WO2013109027A1 - Compound, organic electronic element using same and electronic device thereof - Google Patents
Compound, organic electronic element using same and electronic device thereof Download PDFInfo
- Publication number
- WO2013109027A1 WO2013109027A1 PCT/KR2013/000280 KR2013000280W WO2013109027A1 WO 2013109027 A1 WO2013109027 A1 WO 2013109027A1 KR 2013000280 W KR2013000280 W KR 2013000280W WO 2013109027 A1 WO2013109027 A1 WO 2013109027A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- compound
- aryl
- substituted
- mmol
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 615
- 125000003118 aryl group Chemical group 0.000 claims description 58
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 42
- 229910052805 deuterium Inorganic materials 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 125000003342 alkenyl group Chemical group 0.000 claims description 33
- 230000005525 hole transport Effects 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052698 phosphorus Inorganic materials 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 125000005842 heteroatom Chemical group 0.000 claims description 23
- 239000011368 organic material Substances 0.000 claims description 22
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 21
- 125000002560 nitrile group Chemical group 0.000 claims description 21
- 229910052722 tritium Inorganic materials 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 15
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 14
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 13
- 125000005264 aryl amine group Chemical group 0.000 claims description 13
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 150000002825 nitriles Chemical class 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 6
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 5
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000005567 fluorenylene group Chemical group 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 3
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 3
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 3
- 125000006744 (C2-C60) alkenyl group Chemical group 0.000 claims description 2
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 238000005286 illumination Methods 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 230000007423 decrease Effects 0.000 abstract description 4
- 238000004020 luminiscence type Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 123
- 230000015572 biosynthetic process Effects 0.000 description 103
- 238000003786 synthesis reaction Methods 0.000 description 102
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 56
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 38
- 238000001308 synthesis method Methods 0.000 description 38
- 230000000052 comparative effect Effects 0.000 description 35
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 28
- 239000000463 material Substances 0.000 description 28
- 239000007858 starting material Substances 0.000 description 27
- 238000002347 injection Methods 0.000 description 22
- 239000007924 injection Substances 0.000 description 22
- 229910000027 potassium carbonate Inorganic materials 0.000 description 19
- 239000007832 Na2SO4 Substances 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 229910052938 sodium sulfate Inorganic materials 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000012044 organic layer Substances 0.000 description 16
- 235000010290 biphenyl Nutrition 0.000 description 14
- 239000004305 biphenyl Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229960001866 silicon dioxide Drugs 0.000 description 12
- GWOAJJWBCSUGHH-UHFFFAOYSA-N 1-bromo-4-(4-iodophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(I)C=C1 GWOAJJWBCSUGHH-UHFFFAOYSA-N 0.000 description 10
- 238000000434 field desorption mass spectrometry Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- LOXUVZPMEXKUEJ-UHFFFAOYSA-N 2-bromo-7-iodo-9,9-dimethylfluorene Chemical compound C1=C(I)C=C2C(C)(C)C3=CC(Br)=CC=C3C2=C1 LOXUVZPMEXKUEJ-UHFFFAOYSA-N 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 8
- -1 borate compound Chemical class 0.000 description 8
- 0 CC*ON(C)C Chemical compound CC*ON(C)C 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 4
- LPYXADUZSWBHCT-UHFFFAOYSA-N 5-phenyl-1h-indole Chemical compound C=1C=C2NC=CC2=CC=1C1=CC=CC=C1 LPYXADUZSWBHCT-UHFFFAOYSA-N 0.000 description 4
- ROEOVWIEALGNLM-UHFFFAOYSA-N 5h-benzo[b]carbazole Chemical compound C1=CC=C2C=C3C4=CC=CC=C4NC3=CC2=C1 ROEOVWIEALGNLM-UHFFFAOYSA-N 0.000 description 4
- UGFOTZLGPPWNPY-UHFFFAOYSA-N 7h-benzo[c]carbazole Chemical compound C1=CC=CC2=C3C4=CC=CC=C4NC3=CC=C21 UGFOTZLGPPWNPY-UHFFFAOYSA-N 0.000 description 4
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 4
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 125000001041 indolyl group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 3
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- 150000002475 indoles Chemical group 0.000 description 3
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 2
- VXZCZCODBREKPY-UHFFFAOYSA-N 1-bromo-4-(3-iodophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC(I)=C1 VXZCZCODBREKPY-UHFFFAOYSA-N 0.000 description 2
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 2
- GYGKJNGSQQORRG-UHFFFAOYSA-N 2,3-diphenyl-1h-indole Chemical compound C1=CC=CC=C1C1=C(C=2C=CC=CC=2)C2=CC=CC=C2N1 GYGKJNGSQQORRG-UHFFFAOYSA-N 0.000 description 2
- CRJISNQTZDMKQD-UHFFFAOYSA-N 2-bromodibenzofuran Chemical compound C1=CC=C2C3=CC(Br)=CC=C3OC2=C1 CRJISNQTZDMKQD-UHFFFAOYSA-N 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 2
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 2
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 2
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 2
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 2
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 description 2
- STJXCDGCXVZHDU-UHFFFAOYSA-N 7H-Dibenzo[c,g]carbazole Chemical compound N1C2=CC=C3C=CC=CC3=C2C2=C1C=CC1=CC=CC=C12 STJXCDGCXVZHDU-UHFFFAOYSA-N 0.000 description 2
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 2
- 238000006887 Ullmann reaction Methods 0.000 description 2
- 229910001508 alkali metal halide Inorganic materials 0.000 description 2
- 150000008045 alkali metal halides Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- FFYZMBQLAYDJIG-UHFFFAOYSA-N dibenzofuran-2-amine Chemical compound C1=CC=C2C3=CC(N)=CC=C3OC2=C1 FFYZMBQLAYDJIG-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 2
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
- UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
- MJUVRTYWUMPBTR-MRXNPFEDSA-N 1-(2,2-difluoro-1,3-benzodioxol-5-yl)-n-[1-[(2r)-2,3-dihydroxypropyl]-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)indol-5-yl]cyclopropane-1-carboxamide Chemical compound FC=1C=C2N(C[C@@H](O)CO)C(C(C)(CO)C)=CC2=CC=1NC(=O)C1(C=2C=C3OC(F)(F)OC3=CC=2)CC1 MJUVRTYWUMPBTR-MRXNPFEDSA-N 0.000 description 1
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- HIYWOHBEPVGIQN-UHFFFAOYSA-N 1h-benzo[g]indole Chemical compound C1=CC=CC2=C(NC=C3)C3=CC=C21 HIYWOHBEPVGIQN-UHFFFAOYSA-N 0.000 description 1
- MBHPOBSZPYEADG-UHFFFAOYSA-N 2-bromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=CC=C3C2=C1 MBHPOBSZPYEADG-UHFFFAOYSA-N 0.000 description 1
- WNXNWOBGPRKOJF-UHFFFAOYSA-N 2-bromo-9,9-diphenylfluorene Chemical compound C12=CC(Br)=CC=C2C2=CC=CC=C2C1(C=1C=CC=CC=1)C1=CC=CC=C1 WNXNWOBGPRKOJF-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 1
- KUBSCXXKQGDPPD-UHFFFAOYSA-N 3-bromo-9-phenylcarbazole Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 KUBSCXXKQGDPPD-UHFFFAOYSA-N 0.000 description 1
- ALGIYXGLGIECNT-UHFFFAOYSA-N 3h-benzo[e]indole Chemical compound C1=CC=C2C(C=CN3)=C3C=CC2=C1 ALGIYXGLGIECNT-UHFFFAOYSA-N 0.000 description 1
- VJPPLCNBDLZIFG-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C(=C(NC2=C(C=C1F)C(=O)N)C)C VJPPLCNBDLZIFG-ZDUSSCGKSA-N 0.000 description 1
- YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
- GJXAVNQWIVUQOD-UHFFFAOYSA-N 4-bromodibenzothiophene Chemical compound S1C2=CC=CC=C2C2=C1C(Br)=CC=C2 GJXAVNQWIVUQOD-UHFFFAOYSA-N 0.000 description 1
- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OGSSKPOAXPTJCP-UHFFFAOYSA-N Brc(cc1)ccc1-c(cc1)ccc1-[n](cc1)c(cc2)c1cc2-c1ccccc1 Chemical compound Brc(cc1)ccc1-c(cc1)ccc1-[n](cc1)c(cc2)c1cc2-c1ccccc1 OGSSKPOAXPTJCP-UHFFFAOYSA-N 0.000 description 1
- HLKNORYAUCOWPT-UHFFFAOYSA-N Brc(cc1)ccc1-c(cc1)ccc1-c(cc1)cc(c2c3cccc2)c1[n]3-c1ccccc1 Chemical compound Brc(cc1)ccc1-c(cc1)ccc1-c(cc1)cc(c2c3cccc2)c1[n]3-c1ccccc1 HLKNORYAUCOWPT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
- SNHAYZONDJVBLO-LURJTMIESA-N C1C2=C[C@@H]1CCC2 Chemical compound C1C2=C[C@@H]1CCC2 SNHAYZONDJVBLO-LURJTMIESA-N 0.000 description 1
- LEHAJOKVFVIBSH-UHFFFAOYSA-N C1C=CC(C2(c(cc(cc3)N(c(cc4)ccc4-c4ccccc4)c(cc4)ccc4-c(cc4)ccc4-[n]4c5ccccc5cc4-c4ccccc4)c3-c3ccccc23)c2ccccc2)=CC1 Chemical compound C1C=CC(C2(c(cc(cc3)N(c(cc4)ccc4-c4ccccc4)c(cc4)ccc4-c(cc4)ccc4-[n]4c5ccccc5cc4-c4ccccc4)c3-c3ccccc23)c2ccccc2)=CC1 LEHAJOKVFVIBSH-UHFFFAOYSA-N 0.000 description 1
- QIYSRKUHEWJQBL-UHFFFAOYSA-N C=C1c(cccc2)c2-c2ccccc2C1 Chemical compound C=C1c(cccc2)c2-c2ccccc2C1 QIYSRKUHEWJQBL-UHFFFAOYSA-N 0.000 description 1
- ZCZXQKGUOXFVEJ-UHFFFAOYSA-N CC(C)(C)c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)cc(C(C)(C)c2c3)c1-c2ccc3N(C1C=Cc2ccccc2C11)c2c1c(cccc1)c1cc2 Chemical compound CC(C)(C)c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)cc(C(C)(C)c2c3)c1-c2ccc3N(C1C=Cc2ccccc2C11)c2c1c(cccc1)c1cc2 ZCZXQKGUOXFVEJ-UHFFFAOYSA-N 0.000 description 1
- GEEYQOWRHVSDAQ-UHFFFAOYSA-N CC(C)(C)c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-[n]1c2cc(cccc3)c3cc2c2c1cccc2 Chemical compound CC(C)(C)c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-[n]1c2cc(cccc3)c3cc2c2c1cccc2 GEEYQOWRHVSDAQ-UHFFFAOYSA-N 0.000 description 1
- ZZYGWYLMEQLWMH-UHFFFAOYSA-N CC(C)(C)c(cc1)ccc1N(c1ccccc1)c(cc1C2(C)C)ccc1-c(cc1)c2cc1-[n]1c2cc(cccc3)c3cc2c2ccccc12 Chemical compound CC(C)(C)c(cc1)ccc1N(c1ccccc1)c(cc1C2(C)C)ccc1-c(cc1)c2cc1-[n]1c2cc(cccc3)c3cc2c2ccccc12 ZZYGWYLMEQLWMH-UHFFFAOYSA-N 0.000 description 1
- QAVDURNUXOKRCL-UHFFFAOYSA-N CC(C)(c1c2)c(cc(cc3)-[n]4c5cc(cccc6)c6cc5c5ccccc45)c3-c1ccc2N(c1ccccc1)c1ccc2OC3C=CC=CC3c2c1 Chemical compound CC(C)(c1c2)c(cc(cc3)-[n]4c5cc(cccc6)c6cc5c5ccccc45)c3-c1ccc2N(c1ccccc1)c1ccc2OC3C=CC=CC3c2c1 QAVDURNUXOKRCL-UHFFFAOYSA-N 0.000 description 1
- LDZMKSUHCCYMEJ-UHFFFAOYSA-N CC(C)(c1c2)c3cc(Br)ccc3-c1ccc2-[n]1c2ccccc2cc1-c1ccccc1 Chemical compound CC(C)(c1c2)c3cc(Br)ccc3-c1ccc2-[n]1c2ccccc2cc1-c1ccccc1 LDZMKSUHCCYMEJ-UHFFFAOYSA-N 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C Chemical compound CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- UBASCOPZFCGGAV-UHFFFAOYSA-N CC1(C)OB(c(cc2)cc(c3ccccc33)c2[n]3-c2ccccc2)OC1(C)C Chemical compound CC1(C)OB(c(cc2)cc(c3ccccc33)c2[n]3-c2ccccc2)OC1(C)C UBASCOPZFCGGAV-UHFFFAOYSA-N 0.000 description 1
- PSHMBYOXTCUCJK-UHFFFAOYSA-N CC1(C)c(cc(cc2)Br)c2-c(cc2)c1cc2-[n](cc1)c(cc2)c1cc2-c1ccccc1 Chemical compound CC1(C)c(cc(cc2)Br)c2-c(cc2)c1cc2-[n](cc1)c(cc2)c1cc2-c1ccccc1 PSHMBYOXTCUCJK-UHFFFAOYSA-N 0.000 description 1
- VTNZXLGEJVMWDC-UHFFFAOYSA-N CC1(C)c(cc(cc2)N(c(cc3)ccc3-c3ccccc3)c3cc(-c(cc4)cc(c5ccccc55)c4[n]5-c(cc4)ccc4-c4ccccc4)ccc3)c2-c2c1cccc2 Chemical compound CC1(C)c(cc(cc2)N(c(cc3)ccc3-c3ccccc3)c3cc(-c(cc4)cc(c5ccccc55)c4[n]5-c(cc4)ccc4-c4ccccc4)ccc3)c2-c2c1cccc2 VTNZXLGEJVMWDC-UHFFFAOYSA-N 0.000 description 1
- QHUWSCGRKIYGKW-UHFFFAOYSA-N CC1(C)c(cc(cc2)N(c(cc3)ccc3-c3ccccc3)c3cc(-c(cc4)cc(c5ccccc55)c4[n]5-c4ccccc4)ccc3)c2-c2c1cccc2 Chemical compound CC1(C)c(cc(cc2)N(c(cc3)ccc3-c3ccccc3)c3cc(-c(cc4)cc(c5ccccc55)c4[n]5-c4ccccc4)ccc3)c2-c2c1cccc2 QHUWSCGRKIYGKW-UHFFFAOYSA-N 0.000 description 1
- UVPCEUGWHCMDKE-UHFFFAOYSA-N CC1(C)c(cc(cc2)N(c3ccccc3)c(cc3)ccc3-c(cc3)ccc3N(c3ccccc3)c3cccc4ccccc34)c2-c2ccccc12 Chemical compound CC1(C)c(cc(cc2)N(c3ccccc3)c(cc3)ccc3-c(cc3)ccc3N(c3ccccc3)c3cccc4ccccc34)c2-c2ccccc12 UVPCEUGWHCMDKE-UHFFFAOYSA-N 0.000 description 1
- NRYKVVVCAMCHGP-UHFFFAOYSA-N CC1(C)c2cc(-[n](c(-c3ccccc3)c3)c4c3cccc4)ccc2-c(cc2)c1cc2N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c1ccccc1 Chemical compound CC1(C)c2cc(-[n](c(-c3ccccc3)c3)c4c3cccc4)ccc2-c(cc2)c1cc2N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c1ccccc1 NRYKVVVCAMCHGP-UHFFFAOYSA-N 0.000 description 1
- KYNRCKNSNZDZLB-UHFFFAOYSA-N CC1(C)c2cc(-[n](c3c4c(cccc5)c5cc3)c3c4c(cccc4)c4cc3)ccc2-c(cc2)c1cc2N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1N(c1ccccc1)c1ccccc1 Chemical compound CC1(C)c2cc(-[n](c3c4c(cccc5)c5cc3)c3c4c(cccc4)c4cc3)ccc2-c(cc2)c1cc2N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1N(c1ccccc1)c1ccccc1 KYNRCKNSNZDZLB-UHFFFAOYSA-N 0.000 description 1
- ZZILPJLLMMNQFD-UHFFFAOYSA-N CC1(C)c2cc(-[n](c3c4cccc3)c3c4c4ccccc4cc3)ccc2-c(cc2)c1cc2N(c1ccccc1)c(cc1)ccc1-c1ccccc1 Chemical compound CC1(C)c2cc(-[n](c3c4cccc3)c3c4c4ccccc4cc3)ccc2-c(cc2)c1cc2N(c1ccccc1)c(cc1)ccc1-c1ccccc1 ZZILPJLLMMNQFD-UHFFFAOYSA-N 0.000 description 1
- OKSRKNAMHZKAIY-UHFFFAOYSA-N CC1(C)c2cc(-[n](c3c4cccc3)c3c4c4ccccc4cc3)ccc2-c(cc2)c1cc2N(c1ccccc1)c1cc2ccccc2cc1 Chemical compound CC1(C)c2cc(-[n](c3c4cccc3)c3c4c4ccccc4cc3)ccc2-c(cc2)c1cc2N(c1ccccc1)c1cc2ccccc2cc1 OKSRKNAMHZKAIY-UHFFFAOYSA-N 0.000 description 1
- FEXVHWJPYQOFEG-UHFFFAOYSA-N CC1(C)c2cc(-[n](c3c4cccc3)c3c4c4ccccc4cc3)ccc2-c(cc2)c1cc2N(c1ccccc1)c1cccc2c1cccc2 Chemical compound CC1(C)c2cc(-[n](c3c4cccc3)c3c4c4ccccc4cc3)ccc2-c(cc2)c1cc2N(c1ccccc1)c1cccc2c1cccc2 FEXVHWJPYQOFEG-UHFFFAOYSA-N 0.000 description 1
- NDWYUAPEJPOFEU-UHFFFAOYSA-N CC1(C)c2cc(-[n](c3c4cccc3)c3c4c4ccccc4cc3)ccc2-c(cc2)c1cc2N(c1ccccc1)c1ccccc1 Chemical compound CC1(C)c2cc(-[n](c3c4cccc3)c3c4c4ccccc4cc3)ccc2-c(cc2)c1cc2N(c1ccccc1)c1ccccc1 NDWYUAPEJPOFEU-UHFFFAOYSA-N 0.000 description 1
- IKPMAYHRPNIAMN-UHFFFAOYSA-N CC1(C)c2cc(-[n]3c(cccc4)c4c4ccccc34)ccc2-c(cc2)c1cc2N(c1ccccc1)c1cccc2c1cccc2 Chemical compound CC1(C)c2cc(-[n]3c(cccc4)c4c4ccccc34)ccc2-c(cc2)c1cc2N(c1ccccc1)c1cccc2c1cccc2 IKPMAYHRPNIAMN-UHFFFAOYSA-N 0.000 description 1
- PZHWUMDVIZESHU-UHFFFAOYSA-N CC1(C)c2cc(-[n]3c4cc(cccc5)c5cc4c4c3cccc4)ccc2-c(cc2)c1cc2N(c1ccccc1)c(cc1)ccc1N(c1ccccc1)c1ccccc1 Chemical compound CC1(C)c2cc(-[n]3c4cc(cccc5)c5cc4c4c3cccc4)ccc2-c(cc2)c1cc2N(c1ccccc1)c(cc1)ccc1N(c1ccccc1)c1ccccc1 PZHWUMDVIZESHU-UHFFFAOYSA-N 0.000 description 1
- MHTGKIBQEWXULA-UHFFFAOYSA-N CC1(C)c2cc(-[n]3c4cc(cccc5)c5cc4c4c3cccc4)ccc2-c(cc2)c1cc2N(c1ccccc1)c(cc12)ccc1-c1ccccc1C2(c1ccccc1)c1ccccc1 Chemical compound CC1(C)c2cc(-[n]3c4cc(cccc5)c5cc4c4c3cccc4)ccc2-c(cc2)c1cc2N(c1ccccc1)c(cc12)ccc1-c1ccccc1C2(c1ccccc1)c1ccccc1 MHTGKIBQEWXULA-UHFFFAOYSA-N 0.000 description 1
- XSAFGSWARVCCHB-UHFFFAOYSA-N CC1(C)c2cc(-[n]3c4cc(cccc5)c5cc4c4c3cccc4)ccc2-c(cc2)c1cc2N(c1ccccc1)c1ccc2-c3ccccc3C3(c4ccccc4-c4c3cccc4)c2c1 Chemical compound CC1(C)c2cc(-[n]3c4cc(cccc5)c5cc4c4c3cccc4)ccc2-c(cc2)c1cc2N(c1ccccc1)c1ccc2-c3ccccc3C3(c4ccccc4-c4c3cccc4)c2c1 XSAFGSWARVCCHB-UHFFFAOYSA-N 0.000 description 1
- REALJXPZKITOQI-UHFFFAOYSA-N CC1(C)c2cc(-[n]3c4cc(cccc5)c5cc4c4ccccc34)ccc2-c(cc2)c1cc2N(c1ccccc1)c1ccc2[s]c3ccccc3c2c1 Chemical compound CC1(C)c2cc(-[n]3c4cc(cccc5)c5cc4c4ccccc34)ccc2-c(cc2)c1cc2N(c1ccccc1)c1ccc2[s]c3ccccc3c2c1 REALJXPZKITOQI-UHFFFAOYSA-N 0.000 description 1
- YEPDNSYOPNPAGH-UHFFFAOYSA-N CC1(C)c2cc(-[n]3c4ccccc4c4c3cccc4)ccc2-c(cc2)c1cc2N(c(cc1)ccc1-c(cc1)ccc1F)C1=CCCC=C1 Chemical compound CC1(C)c2cc(-[n]3c4ccccc4c4c3cccc4)ccc2-c(cc2)c1cc2N(c(cc1)ccc1-c(cc1)ccc1F)C1=CCCC=C1 YEPDNSYOPNPAGH-UHFFFAOYSA-N 0.000 description 1
- UWVXNYJWEDBCIE-UHFFFAOYSA-N CC1(C)c2cc(-[n]3c4ccccc4c4c3cccc4)ccc2-c(cc2)c1cc2N(c1ccccc1)c(cc1)ccc1-c1cccc2c1cccc2 Chemical compound CC1(C)c2cc(-[n]3c4ccccc4c4c3cccc4)ccc2-c(cc2)c1cc2N(c1ccccc1)c(cc1)ccc1-c1cccc2c1cccc2 UWVXNYJWEDBCIE-UHFFFAOYSA-N 0.000 description 1
- KHVAGRHCACLWED-UHFFFAOYSA-N CC1(C)c2cc(-[n]3c4ccccc4c4c3cccc4)ccc2-c(cc2)c1cc2N(c1ccccc1)c(cc1)ccc1-c1ccccc1 Chemical compound CC1(C)c2cc(-[n]3c4ccccc4c4c3cccc4)ccc2-c(cc2)c1cc2N(c1ccccc1)c(cc1)ccc1-c1ccccc1 KHVAGRHCACLWED-UHFFFAOYSA-N 0.000 description 1
- AXSPNKHXMNCBRO-UHFFFAOYSA-N CC1(C)c2cc(-[n]3c4ccccc4c4c3cccc4)ccc2-c(cc2)c1cc2N(c1ccccc1)c(cc1)ccc1-c1ncccn1 Chemical compound CC1(C)c2cc(-[n]3c4ccccc4c4c3cccc4)ccc2-c(cc2)c1cc2N(c1ccccc1)c(cc1)ccc1-c1ncccn1 AXSPNKHXMNCBRO-UHFFFAOYSA-N 0.000 description 1
- KRHBGCQYWIQZGI-UHFFFAOYSA-N CC1(C)c2cc(-[n]3c4ccccc4c4c3cccc4)ccc2-c(cc2)c1cc2N(c1ccccc1)c(cc1)ccc1OC Chemical compound CC1(C)c2cc(-[n]3c4ccccc4c4c3cccc4)ccc2-c(cc2)c1cc2N(c1ccccc1)c(cc1)ccc1OC KRHBGCQYWIQZGI-UHFFFAOYSA-N 0.000 description 1
- PPPOHTBKNFPBMM-UHFFFAOYSA-N CC1(C)c2cc(-[n]3c4ccccc4c4c3cccc4)ccc2-c(cc2)c1cc2N(c1ccccc1)c1cc2ccccc2cc1 Chemical compound CC1(C)c2cc(-[n]3c4ccccc4c4c3cccc4)ccc2-c(cc2)c1cc2N(c1ccccc1)c1cc2ccccc2cc1 PPPOHTBKNFPBMM-UHFFFAOYSA-N 0.000 description 1
- YYNHZXXWWHGQEM-UHFFFAOYSA-N CC1(C)c2cc(-[n]3c4ccccc4c4c3cccc4)ccc2-c(cc2)c1cc2N(c1ccccc1)c1ccccc1 Chemical compound CC1(C)c2cc(-[n]3c4ccccc4c4c3cccc4)ccc2-c(cc2)c1cc2N(c1ccccc1)c1ccccc1 YYNHZXXWWHGQEM-UHFFFAOYSA-N 0.000 description 1
- WKFDUSKRJPGIPE-UHFFFAOYSA-N CC1(C)c2cc(N(c3ccccc3)c(cc3)cc(C(C)(C)c4c5)c3-c4ccc5-[n]3c4cc(cccc5)c5cc4c4c3cccc4)ccc2-c2ccccc12 Chemical compound CC1(C)c2cc(N(c3ccccc3)c(cc3)cc(C(C)(C)c4c5)c3-c4ccc5-[n]3c4cc(cccc5)c5cc4c4c3cccc4)ccc2-c2ccccc12 WKFDUSKRJPGIPE-UHFFFAOYSA-N 0.000 description 1
- GVMYEQUFGUYMTP-COBSHVIPSA-N C[C@@]1(C2)C2CCC1 Chemical compound C[C@@]1(C2)C2CCC1 GVMYEQUFGUYMTP-COBSHVIPSA-N 0.000 description 1
- BLRHMMGNCXNXJL-UHFFFAOYSA-N C[n](cc1)c2c1cccc2 Chemical compound C[n](cc1)c2c1cccc2 BLRHMMGNCXNXJL-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- FEYNFHSRETUBEM-UHFFFAOYSA-N N-[3-(1,1-difluoroethyl)phenyl]-1-(4-methoxyphenyl)-3-methyl-5-oxo-4H-pyrazole-4-carboxamide Chemical compound COc1ccc(cc1)N1N=C(C)C(C(=O)Nc2cccc(c2)C(C)(F)F)C1=O FEYNFHSRETUBEM-UHFFFAOYSA-N 0.000 description 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- 101100311330 Schizosaccharomyces pombe (strain 972 / ATCC 24843) uap56 gene Proteins 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- MGMCMYQEYRDSMY-UHFFFAOYSA-N c(c1c2ccc(-c3ccccc3)c1)c[n]2-c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c1ccccc1 Chemical compound c(c1c2ccc(-c3ccccc3)c1)c[n]2-c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c1ccccc1 MGMCMYQEYRDSMY-UHFFFAOYSA-N 0.000 description 1
- PXIQMSOHMNIKSP-UHFFFAOYSA-N c(c1ccccc11)c(-c2ccccc2)[n]1-c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c1ccccc1 Chemical compound c(c1ccccc11)c(-c2ccccc2)[n]1-c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c1ccccc1 PXIQMSOHMNIKSP-UHFFFAOYSA-N 0.000 description 1
- JQASNSAAXUVQBB-UHFFFAOYSA-N c(c1ccccc11)c(-c2ccccc2)[n]1-c(cc1C2(c3ccccc3)c3ccccc3)ccc1-c(cc1)c2cc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c1ccccc1 Chemical compound c(c1ccccc11)c(-c2ccccc2)[n]1-c(cc1C2(c3ccccc3)c3ccccc3)ccc1-c(cc1)c2cc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c1ccccc1 JQASNSAAXUVQBB-UHFFFAOYSA-N 0.000 description 1
- MVNKTDXINXDUGK-UHFFFAOYSA-N c(c1ccccc11)c(-c2ccccc2)[n]1-c(cc1C2(c3ccccc3)c3ccccc3)ccc1-c(cc1)c2cc1N(c1ccccc1)c(cc1)ccc1-c1ccccc1 Chemical compound c(c1ccccc11)c(-c2ccccc2)[n]1-c(cc1C2(c3ccccc3)c3ccccc3)ccc1-c(cc1)c2cc1N(c1ccccc1)c(cc1)ccc1-c1ccccc1 MVNKTDXINXDUGK-UHFFFAOYSA-N 0.000 description 1
- IDZTYFNUHIIQOR-UHFFFAOYSA-N c(c1ccccc11)c(-c2ccccc2)[n]1-c(cc1C23c4ccccc4-c4ccccc24)ccc1-c(cc1)c3cc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c1ccccc1 Chemical compound c(c1ccccc11)c(-c2ccccc2)[n]1-c(cc1C23c4ccccc4-c4ccccc24)ccc1-c(cc1)c3cc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c1ccccc1 IDZTYFNUHIIQOR-UHFFFAOYSA-N 0.000 description 1
- DDUVDEJLOTVWFJ-UHFFFAOYSA-N c(c1ccccc11)c(-c2ccccc2)[n]1-c(cc1C23c4ccccc4-c4ccccc24)ccc1-c(cc1)c3cc1N(c1ccccc1)c(cc1)ccc1-c1ccccc1 Chemical compound c(c1ccccc11)c(-c2ccccc2)[n]1-c(cc1C23c4ccccc4-c4ccccc24)ccc1-c(cc1)c3cc1N(c1ccccc1)c(cc1)ccc1-c1ccccc1 DDUVDEJLOTVWFJ-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N c(cc1)cc2c1c(cccc1)c1cc2 Chemical compound c(cc1)cc2c1c(cccc1)c1cc2 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- RABLDJLKKPWZEU-UHFFFAOYSA-N c(cc1)ccc1-[n](c1ccccc1c1c2)c1ccc2-c(cc1)ccc1N(c(cc1)cc(C23c4ccccc4-c4c2cccc4)c1-c1c3cccc1)c1cccc2c1cccc2 Chemical compound c(cc1)ccc1-[n](c1ccccc1c1c2)c1ccc2-c(cc1)ccc1N(c(cc1)cc(C23c4ccccc4-c4c2cccc4)c1-c1c3cccc1)c1cccc2c1cccc2 RABLDJLKKPWZEU-UHFFFAOYSA-N 0.000 description 1
- ZZOPNWXNIKKIAM-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c1cc(-c(cc2)cc(c(cc3)c4cc3-c3ccc(C5(c6ccccc6-6)c7cc(N(c(cc8)ccc8-c(cc8c9ccccc99)ccc8[n]9-c(cc8)ccc8-c8ccccc8)c8c(cccc9)c9ccc8)ccc7-c7ccccc57)c-6c3)c2[n]4-c(cc2)ccc2-c2ccccc2)ccc1 Chemical compound c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c1cc(-c(cc2)cc(c(cc3)c4cc3-c3ccc(C5(c6ccccc6-6)c7cc(N(c(cc8)ccc8-c(cc8c9ccccc99)ccc8[n]9-c(cc8)ccc8-c8ccccc8)c8c(cccc9)c9ccc8)ccc7-c7ccccc57)c-6c3)c2[n]4-c(cc2)ccc2-c2ccccc2)ccc1 ZZOPNWXNIKKIAM-UHFFFAOYSA-N 0.000 description 1
- QGASXPAGHAGIKJ-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c1cc(-c(cc2)cc(c3ccccc33)c2[n]3-c2ccccc2)ccc1 Chemical compound c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c1cc(-c(cc2)cc(c3ccccc33)c2[n]3-c2ccccc2)ccc1 QGASXPAGHAGIKJ-UHFFFAOYSA-N 0.000 description 1
- CLCLHJVMIKZUPL-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-[n]1c2cc(cccc3)c3cc2c2c1cccc2 Chemical compound c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-[n]1c2cc(cccc3)c3cc2c2c1cccc2 CLCLHJVMIKZUPL-UHFFFAOYSA-N 0.000 description 1
- QPJHSFVVKUNEDX-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-[n]1c2ccc(cccc3)c3c2c2c1ccc1c2cccc1 Chemical compound c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-[n]1c2ccc(cccc3)c3c2c2c1ccc1c2cccc1 QPJHSFVVKUNEDX-UHFFFAOYSA-N 0.000 description 1
- SCNIUFXZTKWDOI-UHFFFAOYSA-N c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n](c1c2c(cccc3)c3cc1)c1c2c2ccccc2cc1)c1cc2ccccc2cc1 Chemical compound c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n](c1c2c(cccc3)c3cc1)c1c2c2ccccc2cc1)c1cc2ccccc2cc1 SCNIUFXZTKWDOI-UHFFFAOYSA-N 0.000 description 1
- DUCNMEWJRADQDX-UHFFFAOYSA-N c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n](c1c2c(cccc3)c3cc1)c1c2c2ccccc2cc1)c1cccc2c1cccc2 Chemical compound c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n](c1c2c(cccc3)c3cc1)c1c2c2ccccc2cc1)c1cccc2c1cccc2 DUCNMEWJRADQDX-UHFFFAOYSA-N 0.000 description 1
- MBBYKKIOLJTHCX-UHFFFAOYSA-N c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n]1c(c2ccccc2cc2)c2c2ccccc12)c1ccc2[o]c(cccc3)c3c2c1 Chemical compound c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n]1c(c2ccccc2cc2)c2c2ccccc12)c1ccc2[o]c(cccc3)c3c2c1 MBBYKKIOLJTHCX-UHFFFAOYSA-N 0.000 description 1
- KPFLZPJHASIZTR-UHFFFAOYSA-N c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n]1c2c(cccc3)c3ccc2c2c1cccc2)c(cc1)ccc1-c1cccc2c1cccc2 Chemical compound c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n]1c2c(cccc3)c3ccc2c2c1cccc2)c(cc1)ccc1-c1cccc2c1cccc2 KPFLZPJHASIZTR-UHFFFAOYSA-N 0.000 description 1
- FICBPURYYVDXHZ-UHFFFAOYSA-N c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n]1c2c(cccc3)c3ccc2c2ccccc12)c1ccc2[s]c(cccc3)c3c2c1 Chemical compound c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n]1c2c(cccc3)c3ccc2c2ccccc12)c1ccc2[s]c(cccc3)c3c2c1 FICBPURYYVDXHZ-UHFFFAOYSA-N 0.000 description 1
- FIHMPNFTFDJYIZ-UHFFFAOYSA-N c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n]1c2cc(cccc3)c3cc2c2c1cccc2)c1cc2ccccc2cc1 Chemical compound c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n]1c2cc(cccc3)c3cc2c2c1cccc2)c1cc2ccccc2cc1 FIHMPNFTFDJYIZ-UHFFFAOYSA-N 0.000 description 1
- CTOONURJDTYCKG-UHFFFAOYSA-N c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n]1c2cc(cccc3)c3cc2c2ccccc12)c1ccc2[o]c(cccc3)c3c2c1 Chemical compound c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n]1c2cc(cccc3)c3cc2c2ccccc12)c1ccc2[o]c(cccc3)c3c2c1 CTOONURJDTYCKG-UHFFFAOYSA-N 0.000 description 1
- CDDRPWQLKSVOBK-UHFFFAOYSA-N c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n]1c2cc(cccc3)c3cc2c2ccccc12)c1ccc2[s]c(cccc3)c3c2c1 Chemical compound c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n]1c2cc(cccc3)c3cc2c2ccccc12)c1ccc2[s]c(cccc3)c3c2c1 CDDRPWQLKSVOBK-UHFFFAOYSA-N 0.000 description 1
- AADXLGTZKVCEMH-UHFFFAOYSA-N c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n]1c2cc(cccc3)c3cc2c2ccccc12)c1cccc2c1cccc2 Chemical compound c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-[n]1c2cc(cccc3)c3cc2c2ccccc12)c1cccc2c1cccc2 AADXLGTZKVCEMH-UHFFFAOYSA-N 0.000 description 1
- BGJFGOBJGHQCEL-UHFFFAOYSA-N c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c1c(cccc2)c2ccc1)c1cccc2c1[s]c1ccccc21 Chemical compound c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c1c(cccc2)c2ccc1)c1cccc2c1[s]c1ccccc21 BGJFGOBJGHQCEL-UHFFFAOYSA-N 0.000 description 1
- SNEXFJXOAJFPRS-UHFFFAOYSA-N c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c1cccc2c1cccc2)c1cccc2c1[o]c1c2cccc1 Chemical compound c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c1cccc2c1cccc2)c1cccc2c1[o]c1c2cccc1 SNEXFJXOAJFPRS-UHFFFAOYSA-N 0.000 description 1
- JGJFZSZIIHYZTP-UHFFFAOYSA-N c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-[n]1c2cc(cccc3)c3cc2c2ccccc12 Chemical compound c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-[n]1c2cc(cccc3)c3cc2c2ccccc12 JGJFZSZIIHYZTP-UHFFFAOYSA-N 0.000 description 1
- FNAZWIINUOBQAP-UHFFFAOYSA-N c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-[n]1c2ccc(cccc3)c3c2c2c1ccc1c2cccc1 Chemical compound c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-[n]1c2ccc(cccc3)c3c2c2c1ccc1c2cccc1 FNAZWIINUOBQAP-UHFFFAOYSA-N 0.000 description 1
- WBGPYRPXARXTOR-UHFFFAOYSA-N c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-[n]1c2c(cccc3)c3ccc2c2c1cccc2 Chemical compound c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-[n]1c2c(cccc3)c3ccc2c2c1cccc2 WBGPYRPXARXTOR-UHFFFAOYSA-N 0.000 description 1
- NOVHZGVBSNYUTH-UHFFFAOYSA-N c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-[n]1c2cc(cccc3)c3cc2c2c1cccc2 Chemical compound c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1-[n]1c2cc(cccc3)c3cc2c2c1cccc2 NOVHZGVBSNYUTH-UHFFFAOYSA-N 0.000 description 1
- GOJVJICYVKKROB-UHFFFAOYSA-N c(cc1c2c3)ccc1[o]c2ccc3Nc1ccc2[o]c(cccc3)c3c2c1 Chemical compound c(cc1c2c3)ccc1[o]c2ccc3Nc1ccc2[o]c(cccc3)c3c2c1 GOJVJICYVKKROB-UHFFFAOYSA-N 0.000 description 1
- HKCYIZOJOPTKSL-UHFFFAOYSA-N c1ccc(C2(c3cc(N(c(cc4)ccc4-c4ccccc4)c4cccc(-c(cc5)cc(c6ccccc66)c5[n]6-c5ccccc5)c4)ccc3-c3ccccc23)c2ccccc2)cc1 Chemical compound c1ccc(C2(c3cc(N(c(cc4)ccc4-c4ccccc4)c4cccc(-c(cc5)cc(c6ccccc66)c5[n]6-c5ccccc5)c4)ccc3-c3ccccc23)c2ccccc2)cc1 HKCYIZOJOPTKSL-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- FMASTMURQSHELY-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-3-methyl-n-[(2-methyl-1h-indol-4-yl)methyl]pyridine-4-carboxamide Chemical compound C1=CC=C2NC(C)=CC2=C1CN(C=1C(=CC(F)=CC=1)C)C(=O)C1=CC=NC=C1C FMASTMURQSHELY-UHFFFAOYSA-N 0.000 description 1
- VFBILHPIHUPBPZ-UHFFFAOYSA-N n-[[2-[4-(difluoromethoxy)-3-propan-2-yloxyphenyl]-1,3-oxazol-4-yl]methyl]-2-ethoxybenzamide Chemical compound CCOC1=CC=CC=C1C(=O)NCC1=COC(C=2C=C(OC(C)C)C(OC(F)F)=CC=2)=N1 VFBILHPIHUPBPZ-UHFFFAOYSA-N 0.000 description 1
- DOWVMJFBDGWVML-UHFFFAOYSA-N n-cyclohexyl-n-methyl-4-(1-oxidopyridin-1-ium-3-yl)imidazole-1-carboxamide Chemical compound C1=NC(C=2C=[N+]([O-])C=CC=2)=CN1C(=O)N(C)C1CCCCC1 DOWVMJFBDGWVML-UHFFFAOYSA-N 0.000 description 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 101150018444 sub2 gene Proteins 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/805—Electrodes
- H10K50/81—Anodes
- H10K50/814—Anodes combined with auxiliary electrodes, e.g. ITO layer combined with metal lines
Definitions
- the present invention relates to an organic electric element comprising the compound and an electronic device thereof.
- organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
- An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
- the organic layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electrical device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
- Materials used as the organic material layer in the organic electric element may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions.
- the most problematic problem is the life and efficiency of the organic electroluminescent device which is gradually progressing in large areas as life and efficiency.
- Efficiency, lifespan, and driving voltage are related to each other. If the efficiency is increased, the driving voltage is relatively decreased, and as the driving voltage is decreased, the crystallization of organic materials by Joule heating generated during driving decreases, resulting in a longer lifespan. Indicates.
- simply improving the organic layer may not maximize the efficiency. This is because long life and high efficiency can be achieved at the same time when an optimal combination of energy level and T1 value between each organic material layer and intrinsic properties (mobility, interfacial properties, etc.) of the material is achieved.
- a light emitting auxiliary layer must exist between the hole transport layer and the light emitting layer, and different light emission auxiliary according to each light emitting layer (R, G, B) is required. It is time to develop the floor.
- the deposition method is the mainstream in the formation of the OLED device, a situation that requires a material that can withstand a long time, that is, a material having a strong heat resistance characteristics.
- a material constituting the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material.
- a stable and efficient organic material layer for an organic electric device has not been made sufficiently, and therefore, the development of new materials is still required.
- An object of the present invention is to provide an organic electric device using the compound which can improve the high luminous efficiency, low driving voltage, high heat resistance, color purity and life of the device and its electronic device.
- the present invention provides an organic electric device comprising a compound represented by the following formula (1), a light emitting auxiliary layer containing the formula (1) and a hole transport layer represented by the formula (2).
- the present invention provides an electronic device using an organic electric element containing the compound represented by the above formula.
- FIG. 1 is an exemplary view of an organic electroluminescent device according to an embodiment of the present invention.
- halo or halogen as used herein include fluorine, chlorine, bromine, and iodine unless otherwise stated.
- alkyl or “alkyl group” has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.
- alkenyl or “alkynyl” has a double bond or a triple bond having 2 to 60 carbon atoms, respectively, unless otherwise specified, but is not limited thereto.
- cycloalkyl refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.
- alkoxy group used in the present invention has a carbon number of 1 to 60 unless otherwise stated, it is not limited thereto.
- aryl group and “arylene group” have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.
- an aryl group or an arylene group means a monocyclic or heterocyclic aromatic, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction.
- the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.
- heteroalkyl means an alkyl including one or more heteroatoms unless otherwise indicated.
- heteroaryl group or “heteroarylene group” means an aryl group or arylene group having 3 to 60 carbon atoms, each of which includes one or more heteroatoms, unless otherwise specified. In addition, it includes not only a single ring but also a heterocycle, and adjacent groups may be formed by bonding.
- heterocycloalkyl and “heterocyclic group” include one or more heteroatoms, unless otherwise specified, have a carbon number from 2 to 60, and include heterocycles as well as monocycles. Adjacent groups may be formed in combination.
- the term 'neighborhood' here means a neighboring flag.
- heterocyclic group may mean an alicyclic and / or aromatic including a heteroatom.
- heteroatom refers to N, O, S, P, and Si unless otherwise indicated.
- aliphatic as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms
- aliphatic ring means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
- saturated or unsaturated ring as used herein means a saturated or unsaturated aliphatic ring or an aromatic ring or heterocyclic ring having 6 to 60 carbon atoms.
- heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.
- substituted in the term “substituted or unsubstituted” as used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 20 alkyl group, C 1 ⁇ C 20 alkoxy groups, C 1 to C 20 alkylamine groups, C 1 to C 20 alkylthiophene groups, C 6 to C 20 arylthiophene groups, C 2 to C 20 alkenyl groups, C 2 to C 20 alkynyl group, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 60 aryl group, C 6 ⁇ C 20 aryl group substituted with deuterium, C 8 ⁇ C 20 aryl alkenyl group, silane group, boron Group, germanium group, and C 5 ⁇ C 20 It is meant to be substituted with one or more substituents selected from the group consisting of, but not limited to these substituents.
- FIG. 1 is an exemplary view of an organic electric device according to an embodiment of the present invention.
- the organic electric device 100 includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110.
- An organic material layer containing a compound represented by the formula (1) between) is provided.
- the first electrode 120 may be an anode (anode)
- the second electrode 180 may be a cathode (cathode)
- the first electrode may be a cathode and the second electrode may be an anode.
- the organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence. At this time, the remaining layers except for the light emitting layer 150 may not be formed.
- the hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, the buffer layer 141 may be further included, and the electron transport layer 160 may serve as the hole blocking layer.
- the organic electronic device according to the present invention may further include a protective layer formed on one surface of the first electrode and the second electrode opposite to the organic material layer.
- the compound according to the present invention applied to the organic material layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, the electron injection layer 170, the host of the light emitting layer 150 or the material of the dopant or capping layer Can be used as
- the organic electroluminescent device may be manufactured using a PVD method.
- the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer are formed thereon.
- the organic material layer including the 160 and the electron injection layer 170 it can be prepared by depositing a material that can be used as the cathode 180 thereon.
- the organic layer may be prepared by using a variety of polymer materials, but not by a deposition process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer. It can be prepared in a number of layers. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.
- the organic electric element according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
- the organic electroluminescent device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device.
- OLED organic electroluminescent device
- OPC organic photoconductor
- organic TFT organic transistor
- Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device.
- the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
- An organic electric device includes an anode, a cathode, and an organic material layer formed therebetween, and the organic material layer comprises a light emitting auxiliary layer containing a compound represented by the following Chemical Formula 1 and a hole transport layer represented by the following Chemical Formula 2. It may include.
- the compound according to one aspect of the present invention is represented by the following formula (1).
- the compound represented by Chemical Formula 1 is applied to the light emitting auxiliary layer according to the present invention.
- Ar 3 in Formula 2 is , or to be. That is, Formula 2 may be represented by the following formula.
- the compound represented by Chemical Formula 2 may be applied to the hole transport layer.
- n, o and p are integers of 1 to 4, m is an integer of 1 or 2, and when m, n, o, p 2 or more, a plurality of R One , R 2 , R 3 or R 4 Are the same as or different from each other, i) R One , R 2 , R 3 And R 4 Each independently of one another is hydrogen; heavy hydrogen; Tritium; Halogen group; C 6 ⁇ C 60 Aryl group; C One ⁇ C 50 Alkyl groups; C 2 ⁇ C 40 Alkenyl group; C 6 ⁇ C 60 Arylamine group; C containing at least one heteroatom of O, N, S, Si and P 2 ⁇ C 60 Heterocyclic group of; C 6 ⁇ C 60 Of aromatic rings and C 4 ⁇ C 60 Condensed ring groups of aliphatic rings of; Amine group; Nitro group; Nitrile group; Amide group And Selected from the group consisting of silane groups; Or ii) neighboring R One Neighboring R 2 Neigh
- Ar 1 to Ar 7 are each independently a C 6 ⁇ C 60 aryl group, C 2 ⁇ C 60 heteroaryl group containing at least one heteroatom of O, N, S, Si and P, C 2 ⁇ In the group consisting of C 20 alkenyl group, fluorenyl group, C 1 ⁇ C 30 alkoxy group, C 6 ⁇ C 30 aryloxy group, C 6 ⁇ C 60 arylamine group and C 1 ⁇ C 50 alkyl group Is selected.
- R 1 to R 4 and Ar 1 to Ar 7 are an aryl group, each of these is hydrogen, deuterium, tritium, halogen, C 1 ⁇ C 60 alkyl group, C 1 ⁇ C 60 alkoxy group, C 1 C 60 -C 60 alkylamine group, C 6 -C 60 arylamine group, C 1 -C 60 alkylthiophene group, C 6 -C 60 aryl thiophene group, C 2 -C 60 alkenyl group, C 2 ⁇ C 60 of the alkynyl group, C 3 ⁇ C 60 cycloalkyl group, C 6 ⁇ C 60 aryl group, of a C 6 ⁇ C 60 substituted by deuterium aryl group, a C 8 ⁇ arylalkenyl group of C 60, a substituted Or may be substituted with one or more groups selected from the group consisting of an unsubstituted silane group, a substituted or unsubstituted boron group,
- R One To R 4 And Ar One To Ar 7 Is a heterocyclic group, each of these is hydrogen, deuterium, tritium, halogen, C One ⁇ C 60 Alkyl group, C 2 ⁇ C 60 Alkenyl, C One ⁇ C 60 Alkoxy group, C One ⁇ C 60 Alkylamine groups, C 6 ⁇ C 60 Arylamine group, C One ⁇ C 60 Alkylthio group, C 6 ⁇ C 60 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 7 ⁇ C 20 Arylalkyl group, C 8 ⁇ C 20 Aryl alkenyl group, C 2 ⁇ C 20 Heterocyclic group, C 2 ⁇ C 60 It may be substituted with one or more substituents selected from the group consisting of an alkynyl group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted germanium group,
- R One To R 4 And Ar One To Ar 7 When is an alkyl group, each of these is hydrogen, deuterium, tritium, halogen, C One ⁇ C 20 Alkyl group, C 2 ⁇ C 20 Alkenyl, C One ⁇ C 20 Alkoxy group, C 6 ⁇ C 20 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 7 ⁇ C 20 Arylalkyl group, C 8 ⁇ C 20 Aryl alkenyl group, C 2 ⁇ C 20 It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group, a nitrile group and an acetylene group,
- R One To R 4 And Ar One To Ar 7 Is an alkenyl group, each of these is hydrogen, deuterium, tritium, halogen, C One ⁇ C 20 Alkyl group, C 2 ⁇ C 20 Alkenyl, C One ⁇ C 20 Alkoxy group, C 6 ⁇ C 20 Arylamine group, C 6 ⁇ C 60 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 7 ⁇ C 20 Arylalkyl group, C 8 ⁇ C 20 Aryl alkenyl group, C 2 ⁇ C 20 It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group, a nitrile group and an acetylene group,
- each of these is C One ⁇ C 60 Alkyl group, C 2 ⁇ C 60 Alkenyl, C 6 ⁇ C 60 Aryl group and C 8 ⁇ C 60 It may be substituted with one or more groups selected from the group consisting of arylalkenyl group of; Arylene group, nitro group, nitrile group, halogen group, C One ⁇ C 2 Alkyl group, C One ⁇ C 2 Alkoxy group, C 6 ⁇ C 20 Aryl group, C 2 ⁇ C 20 It may be substituted with one or more groups selected from the group consisting of a hetero ring group and an amino group of;
- R One To R 4 And Ar One To Ar 7 When is an alkoxy group, each of these is hydrogen, deuterium, halogen, amino, nitrile, nitro, C One ⁇ C 20 Alkyl group, C 2 ⁇ C 20 Alkenyl, C One ⁇ C 20 Alkoxy group, C 3 ⁇ C 30 Cycloalkyl group, C 2 ⁇ C 30 Heterocycloalkyl group, C 6 ⁇ C 60 Aryl group of C, substituted with deuterium 6 ⁇ C 60 Aryl group and C 2 ⁇ C 60 It may be substituted with one or more groups selected from the group consisting of a heteroaryl group of;
- Ar 1 and Ar 7 are fluorenyl groups, each of them is hydrogen, deuterium, tritium, halogen group, C 2 ⁇ C 20 alkenyl group, C 1 ⁇ C 20 alkoxy group, C 6 ⁇ C 20 Aryl group, C 6 ⁇ C 20 aryl group substituted with deuterium, C 7 ⁇ C 20 arylalkyl group, C 8 ⁇ C 20 aryl alkenyl group, C 1 ⁇ C 50 alkyl group, C 2 ⁇ C 20 hetero May be substituted with one or more substituents selected from the group consisting of a cyclic group, a nitrile group and an acetylene group,
- Ar 1 to Ar 7 are aryloxy groups, each of them is hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C 1 ⁇ C 20 alkyl group, C 2 ⁇ C 20 alkenyl group, C 1 ⁇ C 20 alkoxy group, C 3 ⁇ C 30 cycloalkyl group, C 2 ⁇ C 30 heterocycloalkyl group, C 2 ⁇ C 30 heterocyclic group, C 6 ⁇ C 60 aryl group, C 6 ⁇ substituted with deuterium heteroaryl group of C 60 aryl group and C 2 ⁇ C 60 of which can be optionally substituted with one or more groups selected from the group consisting of;
- R 1 to R 4 and Ar 1 to Ar 7 arylamine group each of which is a halogen group, an amino group, a nitrile group, a nitro group, C 1 ⁇ C 20 alkyl group, C 2 ⁇ C 20 alkenyl group, C 1 C 20 -C 20 alkoxy group, C 3 -C 30 cycloalkyl group, C 2 -C 30 heterocycloalkyl group, C 6 -C 60 aryl group, C 6 -C 20 aryl group substituted with deuterium and C 2 May be substituted with one or more groups selected from the group consisting of C 60 heteroaryl groups)
- Ar 1 and Ar 2 of Formula 1 may be selected from the following aryl group or fluorenyl group.
- L of Formula 1 may be selected from the following groups.
- Formula 1 may be represented by any one of the following Formula 3 to Formula 9 and Formula 15 to Formula 18.
- Chemical Formulas 6 to 8 correspond to the case where adjacent R 1 combines with each other to form one or more aromatic hydrocarbons.
- L, Ar 1 and Ar 2 are the same as defined in the formula (1).
- Formula 15 to Formula 18 is more specifically, in Formula 1,
- R One And R 2 are the same as or different from each other, i) R One And R 2 Each independently of one another is hydrogen; heavy hydrogen; Tritium; Halogen group; C One ⁇ C 50 Alkyl groups; C containing at least one heteroatom of O, N, S, Si and P 2 ⁇ C 60 Heterocyclic group of; C 2 ⁇ C 20 Alkenyl group; C 6 ⁇ C 60 Aryl group; And C 6 ⁇ C 60 An arylamine group; selected from the group consisting of ii) neighboring R One Companion and neighbor R 2 They combine with each other to form at least one ring (where a group that does not form a ring is as defined in i),
- L is a C 6 ⁇ C 60 arylene group; Fluorenylene group; C 3 ⁇ C 60 Hetero arylene group; Or a divalent aliphatic hydrocarbon, each of which is nitro, nitrile, halogen, C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, C 6 -C 20 aryl group, C 2 -C 20 hetero ring May be substituted with a substituent with one or more substituents selected from the group consisting of a group and an amino group,
- Ar 1 and Ar 2 are C 6 ⁇ C 60 An aryl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 2 -C 20 alkenyl group; And fluorenyl groups; This is the case when it is selected from the group consisting of.
- each of a and b is an integer of 1 to 5, and when a and / or b are 2 or more, a plurality of R's 4 Or R 5 Are the same as or different from each other, i) R 4 And R 5 Are each independently of each other 6 ⁇ C 25 Aryl group; And C 2 ⁇ C 20 R is selected from the group consisting of alkenyl groups, or ii) 4 Chicks and neighboring R 5 Each group combines with each other to form at least one ring (where a group that does not form a ring is as defined in i),
- R 4 and R 5 are an aryl group or an alkenyl group , each of them is one selected from the group consisting of hydrogen, C 1 ⁇ C 4 alkyl group, C 2 ⁇ C 6 alkenyl group and C 6 ⁇ C 20 aryl group It may be substituted with the above substituents.
- Formula 2 may be represented by any one of the following Formula 10 to Formula 14, all of the corresponding R 3 or R 4 are bonded to each other to form one or more aromatic hydrocarbons.
- the compound represented by Chemical Formula 1 may be one of the following Compounds 1-1 to 1-150, and the compound represented by Chemical Formula 2 may be the following Compounds 3-1 to 3-76, 4-1 to 4 -108, 5-1 to 5-52, 6-1 to 6-52, 7-1 to 7-64, 8-1 to 8-63, 9-1 to 9-64, 10-1 to 10-52 It may be one of the.
- Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below.
- Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 16 below.
- 2-TNATA a -N 1 -phenylbenzene-1,4-diamine
- the dopant is doped by 90:10 by weight of CBP [4,4'-N, N'-dicarbazole-biphenyl] as a light emitting layer host and Ir (ppy) 3 [tris (2-phenylpyridine) -iridium] as a dopant.
- CBP 4,4'-N, N'-dicarbazole-biphenyl
- Ir (ppy) 3 tris (2-phenylpyridine) -iridium] as a dopant.
- a light emitting layer having a thickness of 30 nm was deposited on the hole transport layer.
- BAlq (1,1'-bisphenyl) -4-oleato) bis (2-methyl-8-quinolineoleito) aluminum
- BAlq (1,1'-bisphenyl) -4-oleato) bis (2-methyl-8-quinolineoleito) aluminum
- BAlq Tris (8-quinolinol) aluminum
- Alq 3 Tris (8-quinolinol) aluminum
- LiF an alkali metal halide
- Al was deposited to a thickness of 150 nm to use an organic light emitting device.
- An organic light emitting diode was manufactured in the same manner as in Example 6, but the hole transport layer was formed using the following Comparative Compound 1 instead of the compound of the present invention.
- the electroluminescent (EL) characteristics of the Example and Comparative Example organic electroluminescent devices manufactured as described above were applied to the PR-650 of photoresearch by applying a forward bias DC voltage, and the measured results were measured at 300 cd / m 2 reference luminance.
- the T90 life was measured using a life measurement instrument manufactured by McScience.
- Table 5 below shows device fabrication and evaluation results of Examples and Comparative Examples to which the compound according to the present invention is applied.
- the indole compound exhibits relatively higher efficiency and lifespan than the compounds of Formula 2.
- the organic electroluminescent device was manufactured by using the compound 4-45 showing the low driving voltage and the indole compound having good efficiency and lifetime as the hole transporting layer and the light emitting auxiliary layer, respectively.
- 2-TNATA was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to form a hole injection layer having a thickness of 60 nm, and then compound 4-45 was vacuum-deposited to a thickness of 20 nm as a hole transport compound on the hole injection layer. A hole transport layer was formed. Next, the compound according to the present invention and the comparative compound were vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emission auxiliary layer.
- CBP 4,4'-N, N'-dicarbazole-biphenyl
- a dopant material as a host material (piq) 2 Ir (acac) [bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate] was doped in a weight ratio of 95: 5 to deposit a light emitting layer with a thickness of 30 nm.
- (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum hereinafter abbreviated as BAlq
- BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum
- Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was formed into a transport layer to a thickness of 40 nm. Thereafter, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm as an electron injection layer, and then, Al was deposited to a thickness of 150 nm to use an organic light emitting device.
- An organic light emitting diode was manufactured in the same manner as in Example 7, except that the light emitting auxiliary layer was formed using the following Comparative Compound 2 instead of the compound of the present invention.
- An organic light emitting diode was manufactured in the same manner as in Example 7, except that the light emitting auxiliary layer was formed using the following Comparative Compound 3 instead of the compound of the present invention.
- An organic light emitting diode was manufactured in the same manner as in Example 7, except that the light emitting auxiliary layer was formed using the following Comparative Compound 4 instead of the compound of the present invention.
- An organic light emitting diode was manufactured in the same manner as in Example 7, except that the light emitting auxiliary layer was formed using the following Comparative Compound 5 instead of the compound of the present invention.
- the electroluminescent (EL) characteristics of the Example and Comparative Example organic electroluminescent devices manufactured as described above were applied to the PR-650 of photoresearch by applying a forward bias DC voltage, and the measured results were measured at 300 cd / m 2 reference luminance.
- the T90 life was measured using a life measurement instrument manufactured by McScience.
- Table 6 below shows device fabrication and evaluation results of Examples and Comparative Examples to which the compound according to the present invention is applied.
- the compounds of the present invention have a high T1 energy level and a deep HOMO energy level, holes are more smoothly transported from the hole transport layer to the light emitting layer, and excitons are confined in the light emitting layer, thereby realizing excellent organic electroluminescent devices. Because this is possible.
- the indole core substituted with a phenyl group has improved efficiency and lifespan than the unsubstituted indole core, and the compound 1-5 of the present invention is an indole core substituted with a phenyl group at position 5,
- the 1-6 lights showed low driving voltage, high efficiency and long life.
- the compound according to the present invention when the compound according to the present invention is applied to an organic electroluminescent device, the device exhibits excellent device characteristics. ), Organic transistors (organic TFTs), monochromatic or white lighting elements, and the like.
- the compound according to the present invention in addition to the hole transport layer or the light emission auxiliary layer, The same effect may be obtained even when used in a hole injection layer, a light emitting layer, a buffer layer, an electron injection layer, an electron transport layer, and the like.
Abstract
The present invention relates to a novel compound, to an organic electronic element using same, and to an electronic device thereof, and the present invention can improve the luminescence efficiency, color purity, and longevity of the element and decrease the driving voltage.
Description
본 발명은 화합물을 포함하는 유기전기소자 및 그 전자 장치에 관한 것이다.The present invention relates to an organic electric element comprising the compound and an electronic device thereof.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛 에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기전기소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물 층은 유기전기소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 등으로 이루어질 수 있다. In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. The organic layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electrical device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
유기전기소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료와 전하수송 재료, 예컨대 정공주입 재료, 정공수송 재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다. Materials used as the organic material layer in the organic electric element may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions.
유기 전기 발광소자에 있어 가장 문제 시 되는 것은 수명과 효율로써 점차 대면적으로 진행되어지는 유기전기 발광소자에 있어서 수명과 효율은 반드시 해결해야 하는 문제점이다. 효율과 수명, 구동전압 등은 서로 연관되어 있으며, 효율을 증가되면 상대적으로 구동전압이 떨어지고, 구동전압이 떨어지면서 구동 시 발생되는 Joule heating에 의한 유기물질의 결정화가 적어져 결과적으로 수명이 높아지는 경향을 나타낸다. 하지만 상기 유기물층을 단순히 개선한다고 하여 효율을 극대화 시킬 수는 없다. 왜냐하면 각 유기물층간의 에너지 level 및 T1 값, 물질의 고유특성(mobility, 계면특성 등)등이 최적의 조합을 이뤘을 때 긴 수명과 높은 효율을 동시에 달성할 수 있기 때문이다. In the organic electroluminescent device, the most problematic problem is the life and efficiency of the organic electroluminescent device which is gradually progressing in large areas as life and efficiency. Efficiency, lifespan, and driving voltage are related to each other.If the efficiency is increased, the driving voltage is relatively decreased, and as the driving voltage is decreased, the crystallization of organic materials by Joule heating generated during driving decreases, resulting in a longer lifespan. Indicates. However, simply improving the organic layer may not maximize the efficiency. This is because long life and high efficiency can be achieved at the same time when an optimal combination of energy level and T1 value between each organic material layer and intrinsic properties (mobility, interfacial properties, etc.) of the material is achieved.
또한, 최근 유기 전기 발광소자에 있어 정공 수송층에서의 발광 문제를 해결하기 위해서는 반드시 정공 수송층과 발광층 사이에 발광보조층이 존재하여야 하며, 각각의 발광층(R, G, B)에 따른 서로 다른 발광 보조층의 개발이 필요한 시점이다. In addition, in order to solve the problem of light emission in the hole transport layer in the organic electroluminescent device, a light emitting auxiliary layer must exist between the hole transport layer and the light emitting layer, and different light emission auxiliary according to each light emitting layer (R, G, B) is required. It is time to develop the floor.
일반적으로 전자 수송층에서 발광층으로 electron이 전달되어지고 hole이 정공 수송층에서 발광층으로 전달되어 recombination이 이루어져 exciton을 형성하게 된다. 하지만 정공 수송층의 사용되는 물질의 경우 낮은 HOMO 값을 가져야 하기 때문에 대부분 낮은 T1 값을 가지며, 이로인해 발광층에서 생성된 exciton이 정공 수송층으로 넘어가게 되어 결과적으로 발광층 내 charge balance가 불균형하여 정공 수송층 계면에서 발광하는 문제가 발생한다. 정공 수송층 계면에서 발광을 하면서 색순도 저하 및 효율 감소 등이 나타나며, 수명이 짧아진다. 따라서 높은 T1 값을 가지며, 정공 수송층 HOMO 에너지 level과 발광층의 HOMO 에너지 level 사이에 HOMO level를 갖는 발광 보조층이 필요한데, 이는 단순히 발광 보조층 물질의 코어의 구조적 특성으로 이루어질 수 없으며, 물질의 코어 및 sub-치환기의 특성이 조합을 이루어졌을 때 가능한 바, 상기와 같은 특성을 갖는 발광 보조층의 개발에 어려움을 겪고 있다.In general, electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer to form recombination to form exciton. However, in the case of the material used for the hole transport layer, since it has to have a low HOMO value, most have a low T1 value, which causes the exciton generated in the light emitting layer to pass to the hole transport layer, resulting in an unbalanced charge balance in the light emitting layer. The problem of light emission occurs. While emitting light at the hole transport layer interface, color purity decreases, efficiency decreases, and the life is shortened. Therefore, there is a need for a light emitting auxiliary layer having a high T1 value and having a HOMO level between the hole transport layer HOMO energy level and the light emitting layer HOMO energy level. When the characteristics of the sub-substituent are combined, it is difficult to develop a light emitting auxiliary layer having the above characteristics.
한편, 유기전기소자의 수명단축 원인 중 하나인 양극전극(ITO)으로부터 금속 산화물이 유기층으로 침투 확산되는 것을 지연시키며, 소자 구동시 발생되는 주울열(Joule heating)에 대해서도 안정된 특성, 즉 높은 유리 전이 온도를 갖는 정공 주입층 재료에 대한 개발이 필요하다. 또한 정공 수송층 재료의 낮은 유리전이 온도는 소자 구동시에 박막 표면의 균일도가 무너지는 특성에 따라 소자수명에 큰 영향을 미치는 것으로 보고되고 있다. 또한, OLED 소자의 형성에 있어서 증착방법이 주류를 이루고 있으며, 이러한 증착방법에 오랫동안 견딜 수 있는 재료 즉 내열성 특성이 강한 재료가 필요한 실정이다. On the other hand, it delays the diffusion of metal oxide into the organic layer from the anode electrode (ITO), which is one of the causes of shortening the life of the organic electronic device, and stable characteristics, that is, high glass transition even for Joule heating generated when driving the device. There is a need for development of a hole injection layer material having a temperature. In addition, the low glass transition temperature of the hole transport layer material has been reported to have a significant effect on the device life, depending on the characteristics of the uniformity of the surface of the thin film when driving the device. In addition, the deposition method is the mainstream in the formation of the OLED device, a situation that requires a material that can withstand a long time, that is, a material having a strong heat resistance characteristics.
전술한 유기전기소자가 갖는 우수한 특징들을 충분히 발휘하기 위해서는 소자 내 유기물층을 이루는 물질, 예컨대 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지 안정하고 효율적인 유기전기소자용 유기물층 재료의 개발이 충분히 이루어지지 않은 상태이며, 따라서 새로운 재료의 개발이 계속 요구되고 있다.In order to fully exhibit the excellent characteristics of the above-described organic electroluminescent device, a material constituting the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material. Although this should be preceded, the development of a stable and efficient organic material layer for an organic electric device has not been made sufficiently, and therefore, the development of new materials is still required.
본 발명은 소자의 높은 발광효율, 낮은 구동전압, 고내열성, 색순도 및 수명을 향상시킬 수 있는 화합물을 이용한 유기전기소자 및 그 전자장치를 제공하는 것을 목적으로 한다. An object of the present invention is to provide an organic electric device using the compound which can improve the high luminous efficiency, low driving voltage, high heat resistance, color purity and life of the device and its electronic device.
일측면에서, 본 발명은 하기 화학식 1로 표시되는 화합물과 상기 화학식 1을 함유하는 발광보조층과 하기 화학식 2로 표시되는 정공수송층을 포함하는 유기전기소자를 제공한다.In one aspect, the present invention provides an organic electric device comprising a compound represented by the following formula (1), a light emitting auxiliary layer containing the formula (1) and a hole transport layer represented by the formula (2).
<화학식 1> <Formula 1>
<화학식 2> <Formula 2>
다른 측면에서, 본 발명은 상기 화학식으로 표시되는 화합물을 함유하는 유기전기소자를 이용한 전자장치를 제공한다.In another aspect, the present invention provides an electronic device using an organic electric element containing the compound represented by the above formula.
본 발명에 따르면 소자의 높은 발광효율, 낮은 구동전압, 고내열성을 달성할 수 있고, 소자의 색순도 및 수명을 크게 향상시킬 수 있다.According to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and color purity and life of the device can be greatly improved.
도 1은 본 발명의 일실시예에 따른 유기전기발광소자의 예시도이다.1 is an exemplary view of an organic electroluminescent device according to an embodiment of the present invention.
이하, 본 발명의 실시예를 첨부된 도면을 참조하여 상세하게 설명한다.Hereinafter, exemplary embodiments of the present invention will be described in detail with reference to the accompanying drawings.
각 도면의 구성요소들에 참조부호를 부가함에 있어서, 동일한 구성요소들에 대해서는 비록 다른 도면상에 표시되더라도 가능한 한 동일한 부호를 가지도록 하고 있음에 유의해야 한다. 또한, 본 발명을 설명함에 있어, 관련된 공지 구성 또는 기능에 대한 구체적인 설명이 본 발명의 요지를 흐릴 수 있다고 판단되는 경우에는 그 상세한 설명은 생략한다.In adding reference numerals to the components of each drawing, it should be noted that the same reference numerals are assigned to the same components as much as possible even though they are shown in different drawings. In addition, in describing the present invention, when it is determined that the detailed description of the related well-known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted.
또한, 본 발명의 구성 요소를 설명하는 데 있어서, 제 1, 제 2, A, B, (a),(b) 등의 용어를 사용할 수 있다. 이러한 용어는 그 구성 요소를 다른 구성 요소와 구별하기 위한 것일 뿐, 그 용어에 의해 해당 구성 요소의 본질이나 차례 또는 순서 등이 한정되지 않는다. 어떤 구성 요소가 다른 구성요소에 "연결", "결합" 또는 "접속"된다고 기재된 경우, 그 구성 요소는 그 다른 구성요소에 직접적으로 연결되거나 또는 접속될 수 있지만, 각 구성 요소 사이에 또 다른 구성 요소가 "연결", "결합" 또는 "접속"될 수도 있다고 이해되어야 할 것이다.In addition, in describing the component of this invention, terms, such as 1st, 2nd, A, B, (a), (b), can be used. These terms are only for distinguishing the components from other components, and the nature, order or order of the components are not limited by the terms. If a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected to or connected to that other component, but there may be another configuration between each component. It is to be understood that the elements may be "connected", "coupled" or "connected".
한편, 본 명세서에서 사용된 용어 "할로" 또는 "할로겐"은 다른 설명이 없는 한 불소, 염소, 브롬, 및 요오드를 포함한다. On the other hand, the terms "halo" or "halogen" as used herein include fluorine, chlorine, bromine, and iodine unless otherwise stated.
본 발명에 사용된 용어 "알킬" 또는 "알킬기"는 다른 설명이 없는 한 1 내지 60의 탄소수를 가지며, 여기에 제한되는 것은 아니다. As used herein, the term "alkyl" or "alkyl group" has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.
본 발명에 사용된 용어 "알케닐" 또는 "알키닐"은 다른 설명이 없는 한 각각 2 내지 60의 탄소수의 이중결합 또는 삼중결합을 가지며, 여기에 제한되는 것은 아니다. As used herein, the term "alkenyl" or "alkynyl" has a double bond or a triple bond having 2 to 60 carbon atoms, respectively, unless otherwise specified, but is not limited thereto.
본 발명에 사용된 용어 "시클로알킬"은 다른 설명이 없는 한 3 내지 60의 탄소수를 갖는 고리를 형성하는 알킬을 의미하며, 여기에 제한되는 것은 아니다. The term "cycloalkyl" as used herein, unless otherwise stated, refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.
본 발명에 사용된 용어 "알콕시기"는 다른 설명이 없는 한 1 내지 60의 탄소수를 가지며, 여기에 제한되는 것은 아니다. The term "alkoxy group" used in the present invention has a carbon number of 1 to 60 unless otherwise stated, it is not limited thereto.
본 발명에 사용된 용어 "아릴기" 및 "아릴렌기"는 다른 설명이 없는 한 각각 6 내지 60의 탄소수를 가지며, 이에 제한되는 것은 아니다. As used herein, the terms "aryl group" and "arylene group" have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.
본 발명에서 아릴기 또는 아릴렌기는 단일환 또는 복소환의 방향족을 의미하며, 이웃한 치환기가 결합 또는 반응에 참여하여 형성된 방향족 링을 포함한다. 예컨대, 아릴기는 페닐기, 비페닐기, 플루오렌기, 스파이로플루오렌기일 수 있다. In the present invention, an aryl group or an arylene group means a monocyclic or heterocyclic aromatic, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.
본 명세서에서 사용된 용어 "헤테로알킬"은 다른 설명이 없는 한 하나 이상의 헤테로원자를 포함하는 알킬을 의미한다. 본 발명에 사용된 용어 "헤테로아릴기" 또는 "헤테로아릴렌기"는 다른 설명이 없는 한 각각 하나 이상의 헤테로원자를 포함하는 탄소수 3 내지 60의 아릴기 또는 아릴렌기를 의미하며, 여기에 제한되는 것은 아니며, 단일환뿐만 아니라 복소환을 포함하며, 이웃한 기가 결합하여 형성될 수도 있다.As used herein, the term “heteroalkyl” means an alkyl including one or more heteroatoms unless otherwise indicated. As used herein, the term "heteroaryl group" or "heteroarylene group" means an aryl group or arylene group having 3 to 60 carbon atoms, each of which includes one or more heteroatoms, unless otherwise specified. In addition, it includes not only a single ring but also a heterocycle, and adjacent groups may be formed by bonding.
본 발명에 사용된 용어 "헤테로시클로알킬", "헤테로고리기"는 다른 설명이 없는 한 하나 또는 그 이상의 헤테로원자를 포함하고, 2 내지 60의 탄소수를 가지며, 단일환뿐만 아니라 복소환을 포함하며, 이웃한 기가 결합하여 형성될 수도 있다. 여기서 '이웃한 기'라 함은 바로 이웃한 기를 말한다. 또한, "헤테로고리기"는 헤테로원자를 포함하는 지환족 및/또는 방향족을 의미할 수 있다.As used herein, the terms "heterocycloalkyl" and "heterocyclic group" include one or more heteroatoms, unless otherwise specified, have a carbon number from 2 to 60, and include heterocycles as well as monocycles. Adjacent groups may be formed in combination. The term 'neighborhood' here means a neighboring flag. In addition, "heterocyclic group" may mean an alicyclic and / or aromatic including a heteroatom.
본 명세서에서 사용된 용어 "헤테로원자"는 다른 설명이 없는 한 N, O, S, P 및 Si를 나타낸다. As used herein, the term “heteroatom” refers to N, O, S, P, and Si unless otherwise indicated.
다른 설명이 없는 한, 본 발명에 사용된 용어 "지방족"은 탄소수 1 내지 60의 지방족 탄화수소를 의미하며, "지방족고리"는 탄소수 3 내지 60의 지방족 탄화수소 고리를 의미한다. Unless otherwise stated, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
다른 설명이 없는 한, 본 발명에 사용된 용어 "포화 또는 불포화 고리"는 포화 또는 불포화 지방족고리 또는 탄소수 6 내지 60의 방향족고리 또는 헤테로고리를 의미한다.Unless otherwise stated, the term "saturated or unsaturated ring" as used herein means a saturated or unsaturated aliphatic ring or an aromatic ring or heterocyclic ring having 6 to 60 carbon atoms.
전술한 헤테로화합물 이외의 그 밖의 다른 헤테로화합물 또는 헤테로라디칼은 하나 이상의 헤테로원자를 포함하며, 여기에 제한되는 것은 아니다. Other heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.
또한 명시적인 설명이 없는 한, 본 발명에서 사용된 용어 "치환 또는 비치환된"에서 "치환"은 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1~C20의 알킬기, C1~C20의 알콕시기, C1~C20의 알킬아민기, C1~C20의 알킬티오펜기, C6~C20의 아릴티오펜기, C2~C20의 알케닐기, C2~C20의 알키닐기, C3~C20의 시클로알킬기, C6~C60의 아릴기, 중수소로 치환된 C6~C20의 아릴기, C8~C20의 아릴알케닐기, 실란기, 붕소기, 게르마늄기, 및 C5~C20의 헤테로고리기로 이루어진 군으로부터 선택되는 1개 이상의 치환기로 치환됨을 의미하며, 이들 치환기에 제한되는 것은 아니다. Also, unless stated otherwise, the term "substituted" in the term "substituted or unsubstituted" as used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ~ C 20 alkyl group, C 1 ~ C 20 alkoxy groups, C 1 to C 20 alkylamine groups, C 1 to C 20 alkylthiophene groups, C 6 to C 20 arylthiophene groups, C 2 to C 20 alkenyl groups, C 2 to C 20 alkynyl group, C 3 ~ C 20 cycloalkyl group, C 6 ~ C 60 aryl group, C 6 ~ C 20 aryl group substituted with deuterium, C 8 ~ C 20 aryl alkenyl group, silane group, boron Group, germanium group, and C 5 ~ C 20 It is meant to be substituted with one or more substituents selected from the group consisting of, but not limited to these substituents.
도 1은 본 발명에 일 실시예에 따른 유기전기소자의 예시도이다.1 is an exemplary view of an organic electric device according to an embodiment of the present invention.
도 1을 참조하면, 본 발명에 따른 유기전기소자(100)는 기판(110) 상에 형성된 제 1전극(120), 제 2전극(180) 및 제 1전극(110)과 제 2전극(180) 사이에 화학식 1로 표시되는 화합물을 포함하는 유기물층을 구비한다. 이때, 제 1전극(120)은 애노드(양극)이고, 제 2전극(180)은 캐소드(음극)일 수 있으며, 인버트형의 경우에는 제 1전극이 캐소드이고 제 2전극이 애노드일 수 있다.Referring to FIG. 1, the organic electric device 100 according to the present invention includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110. An organic material layer containing a compound represented by the formula (1) between) is provided. In this case, the first electrode 120 may be an anode (anode), the second electrode 180 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.
유기물층은 제 1전극(120) 상에 순차적으로 정공주입층(130), 정공수송층(140), 발광층(150), 전자수송층(160) 및 전자주입층(170)을 포함할 수 있다. 이때, 발광층(150)을 제외한 나머지 층들이 형성되지 않을 수 있다. 정공저지층, 전자저지층, 발광보조층(151), 버퍼층(141) 등을 더 포함할 수도 있고, 전자수송층(160) 등이 정공저지층의 역할을 할 수도 있을 것이다. The organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence. At this time, the remaining layers except for the light emitting layer 150 may not be formed. The hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, the buffer layer 141 may be further included, and the electron transport layer 160 may serve as the hole blocking layer.
또한, 미도시하였지만, 본 발명에 따른 유기전기소자는 제 1전극과 제 2전극 중 적어도 일면 중 상기 유기물층과 반대되는 일면에 형성된 보호층을 더 포함할 수 있다. In addition, although not shown, the organic electronic device according to the present invention may further include a protective layer formed on one surface of the first electrode and the second electrode opposite to the organic material layer.
상기 유기물층에 적용되는 본 발명에 따른 화합물은 정공주입층(130), 정공수송층(140), 전자수송층(160), 전자주입층(170), 발광층(150)의 호스트 또는 도펀트 또는 캐핑층의 재료로 사용될 수 있다.The compound according to the present invention applied to the organic material layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, the electron injection layer 170, the host of the light emitting layer 150 or the material of the dopant or capping layer Can be used as
본 발명의 일실시예에 따른 유기전기발광소자는 PVD(physical vapor deposition) 방법을 이용하여 제조될 수 있다. 예컨대, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극(120)을 형성하고, 그 위에 정공주입층(130), 정공수송층(140), 발광층(150), 전자수송층(160) 및 전자주입층(170)을 포함하는 유기물층을 형성한 후, 그 위에 음극(180)으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다.The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a PVD method. For example, the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer are formed thereon. After forming the organic material layer including the 160 and the electron injection layer 170, it can be prepared by depositing a material that can be used as the cathode 180 thereon.
또한, 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 용액 공정 또는 솔벤트 프로세스(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다. 본 발명에 따른 유기물층은 다양한 방법으로 형성될 수 있으므로, 그 형성방법에 의해 본 발명의 권리범위가 제한되는 것은 아니다.In addition, the organic layer may be prepared by using a variety of polymer materials, but not by a deposition process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer. It can be prepared in a number of layers. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.
본 발명에 따른 유기전기소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic electric element according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
또한, 본 발명에 따른 유기전기소자는 유기전기발광소자(OLED), 유기태양전지, 유기감광체(OPC), 유기트랜지스터(유기 TFT), 단색 또는 백색 조명용 소자 중 하나일 수 있다.In addition, the organic electroluminescent device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device.
본 발명의 다른 실시예는 상술한 본 발명의 유기전기소자를 포함하는 디스플레이장치와, 이 디스플레이장치를 제어하는 제어부를 포함하는 전자장치를 포함할 수 있다. 이때, 전자장치는 현재 또는 장래의 유무선 통신단말일 수 있으며, 휴대폰 등의 이동 통신 단말기, PDA, 전자사전, PMP, 리모콘, 네비게이션, 게임기, 각종 TV, 각종 컴퓨터 등 모든 전자장치를 포함한다.Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device. In this case, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
본 발명의 일측면에 따른 유기전기소자는 양극, 음극 및 이들 사이에 형성된 유기물층을 포함하며, 상기 유기물층은 하기 화학식 1로 표시되는 화합물을 함유하는 발광보조층과 하기 화학식 2로 표시되는 정공수송층을 포함할 수 있다.An organic electric device according to an aspect of the present invention includes an anode, a cathode, and an organic material layer formed therebetween, and the organic material layer comprises a light emitting auxiliary layer containing a compound represented by the following Chemical Formula 1 and a hole transport layer represented by the following Chemical Formula 2. It may include.
이하, 본 발명의 일 측면에 따른 유기전기소자에 적용된 화합물 및 그 화합물을 포함하는 유기전기소자에 대하여 설명한다.Hereinafter, a compound applied to an organic electric element according to an aspect of the present invention and an organic electric element including the compound will be described.
본 발명의 일측면에 따른 화합물은 하기 화학식 1로 표시된다.The compound according to one aspect of the present invention is represented by the following formula (1).
[화학식 1] [Formula 1]
상기 화학식 1로 표시되는 화합물은 본 발명에 따른 발광보조층에 적용된다. The compound represented by Chemical Formula 1 is applied to the light emitting auxiliary layer according to the present invention.
[화학식 2][Formula 2]
상기 화학식 2에서 Ar3는 
,
또는 
이다. 즉, 상기 화학식 2는 아래 화학식으로 표시될 수 있을 것이다.Ar 3 in Formula 2 is , or to be. That is, Formula 2 may be represented by the following formula.
상기 화학식 2로 표시되는 화합물은 정공수송층에 적용될 수 있다.The compound represented by Chemical Formula 2 may be applied to the hole transport layer.
상기 화학식 1과 2에서,In Chemical Formulas 1 and 2,
n, o 및 p는 1~4의 정수이고, m은 1 또는 2의 정수이며, m, n, o, p 2 이상인 경우 복수의 R1, R2, R3 또는 R4는 각각 서로 동일하거나 상이하고, i) R1, R2, R3
및 R4 는 각각 서로 독립적으로 수소; 중수소; 삼중수소; 할로겐기; C6~C60의 아릴기; C1~C50의 알킬기; C2~C40의 알케닐기; C6~C60의 아릴아민기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C6~C60의 방향족 고리와 C4~C60의 지방족고리의 축합 고리기; 아민기; 니트로기; 니트릴기; 아미드기 및 실란기로 이루어진 군에서 선택되거나; 또는 ii) 이웃한 R1끼리, 이웃한 R2끼리, 이웃한 R3끼리 및 이웃한 R4끼리 중 적어도 한쌍이 서로 결합하여 적어도 하나의 방향족고리를 형성한다. 이때, 방향족고리를 형성하지 않는 R1, R2, R3
및 R4 는 상기 i)에서 정의된 것과 같다.n, o and p are integers of 1 to 4, m is an integer of 1 or 2, and when m, n, o, p 2 or more, a plurality of ROne, R2, R3 or R4Are the same as or different from each other, i) ROne, R2, R3
And R4 Each independently of one another is hydrogen; heavy hydrogen; Tritium; Halogen group; C6~ C60Aryl group; COne~ C50Alkyl groups; C2~ C40Alkenyl group; C6~ C60Arylamine group; C containing at least one heteroatom of O, N, S, Si and P2~ C60Heterocyclic group of; C6~ C60Of aromatic rings and C4~ C60Condensed ring groups of aliphatic rings of; Amine group; Nitro group; Nitrile group; Amide group And Selected from the group consisting of silane groups; Or ii) neighboring ROneNeighboring R2Neighboring R3Companion and neighbor R4At least one of the pairs combines with each other to form at least one aromatic ring. At this time, R does not form an aromatic ringOne, R2, R3
And R4 Is as defined in i) above.
그리고 화학식 1과 2의 L은 서로 독립적으로, 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; C3~C60의 헤테로 아릴렌기 및 2가의 지방족 탄화수소;로 이루어진 군에서 선택되며(이들 각각은 수소, 중수소, 삼중수소, 니트로, 니트릴, 할로겐, 아세틸렌기, C7~C20의 아릴알킬기, C8~C20의 아릴알케닐기, C1~C50의 알킬기, C2~C20의 알케닐기 C1~C20의 알콕시기, C6~C20의 아릴기, C2~C20의 헤테로 고리기 및 아미노기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환기로 치환될 수 있다),And L in Formula 1 and 2 independently of each other, a single bond; C6~ C60Arylene group; Fluorenylene groups; C3~ C60Hetero arylene group and Divalent aliphatic hydrocarbons; each of which is hydrogen, deuterium, tritium, nitro, nitrile, halogen, acetylene group, C7~ C20Arylalkyl group, C8~ C20Aryl alkenyl group, COne~ C50Alkyl group, C2~ C20Alkenyl group COne~ C20Alkoxy group, C6~ C20Aryl group, C2~ C20May be substituted with one or more substituents selected from the group consisting of a heterocyclic group and an amino group of
Ar1 내지 Ar7은 각각 서로 독립적으로 C6~C60의 아릴기, O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로아릴기, C2~C20의 알케닐기, 플루오렌일기, C1~C30의 알콕시기, C6~C30의 아릴옥시기, C6~C60의 아릴아민기 및 C1~C50의 알킬기로 이루어진 군에서 선택된다.Ar 1 to Ar 7 are each independently a C 6 ~ C 60 aryl group, C 2 ~ C 60 heteroaryl group containing at least one heteroatom of O, N, S, Si and P, C 2 ~ In the group consisting of C 20 alkenyl group, fluorenyl group, C 1 ~ C 30 alkoxy group, C 6 ~ C 30 aryloxy group, C 6 ~ C 60 arylamine group and C 1 ~ C 50 alkyl group Is selected.
(상기 R1 내지 R4 및 Ar1 내지 Ar7가 아릴기인 경우, 이들 각각은 수소, 중수소, 삼중수소, 할로겐기, C1~C60의 알킬기, C1~C60의 알콕시기, C1~C60의 알킬아민기, C6~C60의 아릴아민기, C1~C60의 알킬티오펜기, C6~C60의 아릴 티오펜기, C2~C60의 알케닐기, C2~C60의 알키닐기, C3~C60의 시클로알킬기, C6~C60의 아릴기, 중수소로 치환된 C6~C60의 아릴기, C8~C60의 아릴알케닐기, 치환 또는 비치환된 실란기, 치환 또는 비치환된 붕소기, 치환 또는 비치환된 게르마늄기 및 치환 또는 비치환된 C2~C60의 헤테로고리기로 이루어진 군으로부터 선택된 하나 이상의 기로 치환될 수 있고(단, Ar1 및 Ar2가 아릴기인 경우 상기 치환기 군 중에 중수소, 아미노기, 니트릴기, 니트로기 및 포스핀옥사이드기가 더 포함될 수 있다),(If R 1 to R 4 and Ar 1 to Ar 7 are an aryl group, each of these is hydrogen, deuterium, tritium, halogen, C 1 ~ C 60 alkyl group, C 1 ~ C 60 alkoxy group, C 1 C 60 -C 60 alkylamine group, C 6 -C 60 arylamine group, C 1 -C 60 alkylthiophene group, C 6 -C 60 aryl thiophene group, C 2 -C 60 alkenyl group, C 2 ~ C 60 of the alkynyl group, C 3 ~ C 60 cycloalkyl group, C 6 ~ C 60 aryl group, of a C 6 ~ C 60 substituted by deuterium aryl group, a C 8 ~ arylalkenyl group of C 60, a substituted Or may be substituted with one or more groups selected from the group consisting of an unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted germanium group, and a substituted or unsubstituted C 2 to C 60 heterocyclic group ( , If Ar 1 and Ar 2 is an aryl group, deuterium, amino, nitrile, nitro and phosphine oxide groups may be further included in the substituent group),
R1
내지 R4 및 Ar1 내지 Ar7가 헤테로고리기인 경우, 이들 각각은 수소, 중수소, 삼중수소, 할로겐기, C1~C60의 알킬기, C2~C60의 알케닐기, C1~C60의 알콕시기, C1~C60의 알킬아민기, C6~C60의 아릴아민기, C1~C60의 알킬티오기, C6~C60의 아릴기, 중수소로 치환된 C6~C20의 아릴기, C7~C20의 아릴알킬기, C8~C20의 아릴알케닐기, C2~C20의 헤테로 고리기, C2~C60의 알키닐기, 치환 또는 비치환된 실란기, 치환 또는 비치환된 붕소기, 치환 또는 비치환된 게르마늄기,니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있고,ROne
To R4 And ArOne To Ar7Is a heterocyclic group, each of these is hydrogen, deuterium, tritium, halogen, COne~ C60Alkyl group, C2~ C60Alkenyl, COne~ C60Alkoxy group, COne~ C60Alkylamine groups, C6~ C60Arylamine group, COne~ C60Alkylthio group, C6~ C60Aryl group of C, substituted with deuterium6~ C20Aryl group, C7~ C20Arylalkyl group, C8~ C20Aryl alkenyl group, C2~ C20Heterocyclic group, C2~ C60It may be substituted with one or more substituents selected from the group consisting of an alkynyl group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted germanium group, a nitrile group and an acetylene group,
R1
내지 R4 및 Ar1 내지 Ar7가 알킬기인 경우, 이들 각각은 수소, 중수소, 삼중수소, 할로겐기, C1~C20의 알킬기, C2~C20의 알케닐기, C1~C20의 알콕시기, C6~C20의 아릴기, 중수소로 치환된 C6~C20의 아릴기, C7~C20의 아릴알킬기, C8~C20의 아릴알케닐기, C2~C20의 헤테로 고리기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있고,ROne
To R4 And ArOne To Ar7When is an alkyl group, each of these is hydrogen, deuterium, tritium, halogen, COne~ C20Alkyl group, C2~ C20Alkenyl, COne~ C20Alkoxy group, C6~ C20Aryl group of C, substituted with deuterium6~ C20Aryl group, C7~ C20Arylalkyl group, C8~ C20Aryl alkenyl group, C2~ C20It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group, a nitrile group and an acetylene group,
R1
내지 R4 및 Ar1 내지 Ar7가 알케닐기인 경우, 이들 각각은 수소, 중수소, 삼중수소, 할로겐기, C1~C20의 알킬기, C2~C20의 알케닐기, C1~C20의 알콕시기, C6~C20의 아릴아민기, C6~C60의 아릴기, 중수소로 치환된 C6~C20의 아릴기, C7~C20의 아릴알킬기, C8~C20의 아릴알케닐기, C2~C20의 헤테로 고리기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있고,ROne
To R4 And ArOne To Ar7Is an alkenyl group, each of these is hydrogen, deuterium, tritium, halogen, COne~ C20Alkyl group, C2~ C20Alkenyl, COne~ C20Alkoxy group, C6~ C20Arylamine group, C6~ C60Aryl group of C, substituted with deuterium6~ C20Aryl group, C7~ C20Arylalkyl group, C8~ C20Aryl alkenyl group, C2~ C20It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group, a nitrile group and an acetylene group,
R1
내지 R4이 아민기인 경우, 이들 각각은 C1~C60의 알킬기, C2~C60의 알케닐기, C6~C60의 아릴기 및 C8~C60의 아릴알케닐기로 이루어진 군으로부터 선택된 하나 이상의 기로 치환될 수 있고; 아릴렌기는 니트로기, 니트릴기, 할로겐기, C1~C2의 알킬기, C1~C2의 알콕시기, C6~C20의 아릴기, C2~C20의 헤테로 고리기 및 아미노기로 이루어진 군으로부터 선택된 하나 이상의 기로 치환될 수 있고; ROne
To R4In the case of this amine group, each of these is COne~ C60Alkyl group, C2~ C60Alkenyl, C6~ C60Aryl group and C8~ C60It may be substituted with one or more groups selected from the group consisting of arylalkenyl group of; Arylene group, nitro group, nitrile group, halogen group, COne~ C2Alkyl group, COne~ C2Alkoxy group, C6~ C20Aryl group, C2~ C20It may be substituted with one or more groups selected from the group consisting of a hetero ring group and an amino group of;
R1
내지 R4 및 Ar1 내지 Ar7가 알콕시기인 경우, 이들 각각은 수소, 중수소, 할로겐기, 아미노기, 니트릴기, 니트로기, C1~C20의 알킬기, C2~C20의 알케닐기, C1~C20의 알콕시기, C3~C30의 시클로알킬기, C2~C30의 헤테로시클로알킬기, C6~C60의 아릴기, 중수소로 치환된 C6~C60의 아릴기 및 C2~C60의 헤테로아릴기로 이루어진 군으로부터 선택된 하나 이상의 기로 치환될 수 있고; ROne
To R4 And ArOne To Ar7When is an alkoxy group, each of these is hydrogen, deuterium, halogen, amino, nitrile, nitro, COne~ C20Alkyl group, C2~ C20Alkenyl, COne~ C20Alkoxy group, C3~ C30Cycloalkyl group, C2~ C30Heterocycloalkyl group, C6~ C60Aryl group of C, substituted with deuterium6~ C60Aryl group and C2~ C60It may be substituted with one or more groups selected from the group consisting of a heteroaryl group of;
상기 Ar1 및 Ar7이 플루오렌일기인 경우, 이들 각각은 수소, 중수소, 삼중수소, 할로겐기, C2~C20의 알케닐기, C1~C20의 알콕시기, C6~C20의 아릴기, 중수소로 치환된 C6~C20의 아릴기, C7~C20의 아릴알킬기, C8~C20의 아릴알케닐기, C1~C50의 알킬기, C2~C20의 헤테로 고리기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있고,When Ar 1 and Ar 7 are fluorenyl groups, each of them is hydrogen, deuterium, tritium, halogen group, C 2 ~ C 20 alkenyl group, C 1 ~ C 20 alkoxy group, C 6 ~ C 20 Aryl group, C 6 ~ C 20 aryl group substituted with deuterium, C 7 ~ C 20 arylalkyl group, C 8 ~ C 20 aryl alkenyl group, C 1 ~ C 50 alkyl group, C 2 ~ C 20 hetero May be substituted with one or more substituents selected from the group consisting of a cyclic group, a nitrile group and an acetylene group,
Ar1 내지 Ar7이 아릴옥시기인 경우, 이들 각각은 수소, 중수소, 할로겐기, 아미노기, 니트릴기, 니트로기, C1~C20의 알킬기, C2~C20의 알케닐기, C1~C20의 알콕시기, C3~C30의 시클로알킬기, C2~C30의 헤테로시클로알킬기, C2~C30의 헤테로 고리기, C6~C60의 아릴기, 중수소로 치환된 C6~C60의 아릴기 및 C2~C60의 헤테로아릴기로 이루어진 군으로부터 선택된 하나 이상의 기로 치환될 수 있고; When Ar 1 to Ar 7 are aryloxy groups, each of them is hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C 1 ~ C 20 alkyl group, C 2 ~ C 20 alkenyl group, C 1 ~ C 20 alkoxy group, C 3 ~ C 30 cycloalkyl group, C 2 ~ C 30 heterocycloalkyl group, C 2 ~ C 30 heterocyclic group, C 6 ~ C 60 aryl group, C 6 ~ substituted with deuterium heteroaryl group of C 60 aryl group and C 2 ~ C 60 of which can be optionally substituted with one or more groups selected from the group consisting of;
R1 내지 R4 및 Ar1 내지 Ar7가 아릴아민기인 경우, 이들 각각은 할로겐기, 아미노기, 니트릴기, 니트로기, C1~C20의 알킬기, C2~C20의 알케닐기, C1~C20의 알콕시기, C3~C30의 시클로알킬기, C2~C30의 헤테로시클로알킬기, C6~C60의 아릴기, 중수소로 치환된 C6~C20의 아릴기 및 C2~C60의 헤테로아릴기로 이루어진 군으로부터 선택된 하나 이상의 기로 치환될 수 있다)When the R 1 to R 4 and Ar 1 to Ar 7 arylamine group, each of which is a halogen group, an amino group, a nitrile group, a nitro group, C 1 ~ C 20 alkyl group, C 2 ~ C 20 alkenyl group, C 1 C 20 -C 20 alkoxy group, C 3 -C 30 cycloalkyl group, C 2 -C 30 heterocycloalkyl group, C 6 -C 60 aryl group, C 6 -C 20 aryl group substituted with deuterium and C 2 May be substituted with one or more groups selected from the group consisting of C 60 heteroaryl groups)
한편, 상기 화학식 1의 Ar1과 Ar2는 하기 아릴기 또는 플루오레닐기 중에서 선택될 수 있다.On the other hand, Ar 1 and Ar 2 of Formula 1 may be selected from the following aryl group or fluorenyl group.
또한, 상기 화학식 1의 L은 하기 그룹에서 선택될 수 있다.In addition, L of Formula 1 may be selected from the following groups.
상기 화학식 1은 하기 화학식 3 내지 화학식 9 및 화학식 15 내지 화학식 18 중 어느 하나로 표시될 수 있다. 특히, 화학식 6 내지 8은 이웃한 R1끼리 서로 결합하여 하나 이상의 방향족탄화수소를 형성한 경우에 해당한다.Formula 1 may be represented by any one of the following Formula 3 to Formula 9 and Formula 15 to Formula 18. In particular, Chemical Formulas 6 to 8 correspond to the case where adjacent R 1 combines with each other to form one or more aromatic hydrocarbons.
<화학식 3><Formula 3>
<화학식 4><Formula 4>
<화학식 5><Formula 5>
<화학식 6><Formula 6>
<화학식 7><Formula 7>
<화학식 8><Formula 8>
<화학식 9><Formula 9>
상기 화학식에서, L, Ar1 및 Ar2는 상기 화학식 1에서 정의된 것과 같다.In the above formula, L, Ar 1 and Ar 2 are the same as defined in the formula (1).
상기 화학식 15 내지 화학식 18은 더 자세하게는, 화학식 1에서,Formula 15 to Formula 18 is more specifically, in Formula 1,
m은 1 또는 2의 정수이고, n은 1~4의 정수이며, m 및/또는 n이 2 이상인 경우 복수의 R1 또는 R2는 각각 서로 동일하거나 상이하고, i) R1
및 R2는 각각 서로 독립적으로 수소; 중수소; 삼중수소; 할로겐기; C1~C50의 알킬기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C2~C20의 알케닐기; C6~C60의 아릴기; 및 C6~C60의 아릴아민기;로 이루어진 군에서 선택되거나, 또는 ii)이웃한 R1 끼리 및 이웃한 R2 끼리 서로 결합하여 적어도 하나의 고리를 형성하며(이때, 고리를 형성하지 않는 기는 i)에서 정의된 것과 같음),m is an integer of 1 or 2, n is an integer of 1 to 4, and when m and / or n is 2 or more, a plurality of ROne Or R2Are the same as or different from each other, i) ROne
And R2Each independently of one another is hydrogen; heavy hydrogen; Tritium; Halogen group; COne~ C50Alkyl groups; C containing at least one heteroatom of O, N, S, Si and P2~ C60Heterocyclic group of; C2~ C20Alkenyl group; C6~ C60Aryl group; And C6~ C60An arylamine group; selected from the group consisting of ii) neighboring ROne Companion and neighbor R2 They combine with each other to form at least one ring (where a group that does not form a ring is as defined in i),
L은 C6~C60의 아릴렌기; 플루오레닐렌기; C3~C60의 헤테로 아릴렌기; 또는 2가의 지방족 탄화수소이며, 이들 각각은 니트로, 니트릴, 할로겐, C1~C20의 알킬기, C1~C20의 알콕시기, C6~C20의 아릴기, C2~C20의 헤테로 고리기 및 아미노기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환기로 치환될 수 있고, L is a C 6 ~ C 60 arylene group; Fluorenylene group; C 3 ~ C 60 Hetero arylene group; Or a divalent aliphatic hydrocarbon, each of which is nitro, nitrile, halogen, C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, C 6 -C 20 aryl group, C 2 -C 20 hetero ring May be substituted with a substituent with one or more substituents selected from the group consisting of a group and an amino group,
Ar1 및 Ar2는 C6~C60의 아릴기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C2~C20의 알케닐기; 및 플루오렌일기; 로 이루어진 군에서 선택되는 경우에 해당된다.Ar 1 and Ar 2 are C 6 ~ C 60 An aryl group; C 2 ~ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 2 -C 20 alkenyl group; And fluorenyl groups; This is the case when it is selected from the group consisting of.
그리고 화학식 15 내지 화학식 18에서 a 및 b는 각각 1~5의 정수이며, a 및/또는 b가 2 이상인 경우 복수의 R4 또는 R5는 각각 서로 동일하거나 상이하고, i) R4
및 R5는 각각 서로 독립적으로 C6~C25의 아릴기; 및 C2~C20의 알케닐기로 이루어진 군에서 선택되거나, 또는 ii)이웃한 R4기끼리 및 이웃한 R5기끼리 각각 서로 결합하여 적어도 하나의 고리를 형성하며(이때, 고리를 형성하지 않는 기는 i)에서 정의된 것과 같음),And in Formulas 15 to 18, each of a and b is an integer of 1 to 5, and when a and / or b are 2 or more, a plurality of R's4 Or R5Are the same as or different from each other, i) R4
And R5Are each independently of each other6~ C25Aryl group; And C2~ C20R is selected from the group consisting of alkenyl groups, or ii)4Chicks and neighboring R5Each group combines with each other to form at least one ring (where a group that does not form a ring is as defined in i),
상기 R4 및 R5가 아릴기
또는
알케닐기인 경우, 이들 각각은 수소, C1~C4의 알킬기, C2~C6의 알케닐기 및 C6~C20의 아릴기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있다.When R 4 and R 5 are an aryl group or an alkenyl group , each of them is one selected from the group consisting of hydrogen, C 1 ~ C 4 alkyl group, C 2 ~ C 6 alkenyl group and C 6 ~ C 20 aryl group It may be substituted with the above substituents.
한편, 상기 화학식 2는 하기 화학식 10 내지 화학식 14 중 어느 하나로 표시될 수 있는데, 모두 이웃한 R3 또는 R4끼리 서로 결합하여 하나 이상의 방향족탄화수소를 형성한 경우에 해당한다.On the other hand, Formula 2 may be represented by any one of the following Formula 10 to Formula 14, all of the corresponding R 3 or R 4 are bonded to each other to form one or more aromatic hydrocarbons.
<화학식 14> <Formula 14>
상기 화학식 3 내지 화학식 14에서, L, Ar1, Ar2, Ar4, Ar5, R3, o는 상기 화학식 1 또는 화학식 2에서 정의된 것과 같다.In Formulas 3 to 14, L, Ar 1 , Ar 2 , Ar 4 , Ar 5 , R 3 , o are the same as defined in Formula 1 or Formula 2.
보다 구체적으로, 상기 화학식 1로 표시되는 화합물은 하기 화합물 1-1 ~ 1-150 중 하나일 수 있고, 상기 화학식 2로 표시되는 화합물은 하기 화합물 3-1 ~ 3-76, 4-1 ~ 4-108, 5-1 ~ 5-52, 6-1 ~ 6-52, 7-1 ~ 7-64, 8-1 ~ 8-63, 9-1 ~ 9-64, 10-1 ~ 10-52 중 하나일 수 있다.More specifically, the compound represented by Chemical Formula 1 may be one of the following Compounds 1-1 to 1-150, and the compound represented by Chemical Formula 2 may be the following Compounds 3-1 to 3-76, 4-1 to 4 -108, 5-1 to 5-52, 6-1 to 6-52, 7-1 to 7-64, 8-1 to 8-63, 9-1 to 9-64, 10-1 to 10-52 It may be one of the.
이하에서, 본 발명에 따른 화학식 1 또는 화학식 2로 표시되는 화합물의 합성예 및 유기전기소자의 제조예에 관하여 실시예를 들어 구체적으로 설명하지만, 본 발명이 하기의 실시예로 한정되는 것은 아니다.Hereinafter, the synthesis examples of the compounds represented by the general formula (1) or the general formula (2) according to the present invention and the production examples of the organic electric device will be described in detail by way of examples, the present invention is not limited to the following examples.
합성예Synthesis Example
1 : 화학식 1의 합성 1: Synthesis of Chemical Formula 1
본 발명에 따른 화합물(final products; product 1-1 ~ 1-150)은 하기 반응식 1과 같이 Sub 1과 Sub 2가 반응하여 제조된다.Compounds (final products; products 1-1 to 1-150) according to the present invention are prepared by the reaction of Sub 1 and Sub 2 as in Scheme 1 below.
<반응식 1><Scheme 1>
[실시예 1] Example 1
SubSub
1의 합성 1, synthesis
반응식 1의 sub 1은 하기 반응식 2의 반응경로에 의해 합성될 수 있다.Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below.
<반응식 2><Scheme 2>
Sub 1에 속하는 구체적 화합물의 합성예는 다음과 같다.Synthesis examples of specific compounds belonging to Sub 1 are as follows.
(1) (One)
SubSub
1-1 1-1
합성예Synthesis Example
<반응식 3><Scheme 3>
출발물질인 1H-indole (57.12 g, 487.6 mmol)을 둥근바닥플라스크에 nitrobenzene으로 녹인 후, Sub 1-I-1 (245.06 g, 682.6 mmol), Na2SO4 (69.24 g, 487.6 mmol), K2CO3 (67.29 g, 487.6 mmol), Cu (9.3 g, 146.3 mmol)를 첨가하고 200℃에서 교반하였다. 반응이 완료되면 증류를 통해 nitrobenzene을 제거하고 CH2Cl2와 물로 추출하였다. 유기층을 MgSO4로 건조하고 농축한 후 생성된 화합물을 silicagel column 및 재결정하여 생성물 120.56 g (수율: 71%)를 얻었다.Starting material 1 H -indole (57.12 g, 487.6 mmol) was dissolved in nitrobenzene in a round bottom flask, Sub 1-I-1 (245.06 g, 682.6 mmol), Na 2 SO 4 (69.24 g, 487.6 mmol), K 2 CO 3 (67.29 g, 487.6 mmol), Cu (9.3 g, 146.3 mmol) was added and stirred at 200 ° C. After the reaction was completed, nitrobenzene was removed by distillation and extracted with CH 2 Cl 2 and water. The organic layer was dried over MgSO 4 , concentrated and the resulting compound was silicagel column and recrystallized to give 120.56 g (yield: 71%) of the product.
(2) (2)
SubSub
1-3 1-3
합성예Synthesis Example
<반응식 4><Scheme 4>
출발물질인 5-phenyl-1H-indole (50.82 g, 263 mmol)에 Sub 1-I-1 (132.18 g, 368.2 mmol), Na2SO4 (37.35 g, 263 mmol), K2CO3 (36.29 g, 263 mmol), Cu (5.01 g, 78.9 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-1 합성법을 사용하여 생성물 75.89 g (수율: 68%)를 얻었다.In the starting material 5-phenyl-1 H -indole (50.82 g, 263 mmol), Sub 1-I-1 (132.18 g, 368.2 mmol), Na 2 SO 4 (37.35 g, 263 mmol), K 2 CO 3 ( 36.29 g, 263 mmol), Cu (5.01 g, 78.9 mmol) and nitrobenzene were obtained using the Sub 1-1 synthesis method of Example 1, to obtain 75.89 g (yield: 68%) of the product.
(3) (3)
SubSub
1-5 1-5
합성예Synthesis Example
<반응식 5>Scheme 5
출발물질인 2-phenyl-1H-indole (51.97 g, 268.9 mmol)에 Sub 1-I-1 (135.15 g, 376.5 mmol), Na2SO4
(38.18 g, 268.9 mmol), K2CO3 (37.11 g, 268.9 mmol), Cu (5.13 g, 80.7 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-1 합성법을 사용하여 생성물 71.88 g (수율: 63%)를 얻었다.Starting material 2-phenyl-1H-indole (51.97 g, 268.9 mmol) in Sub 1-I-1 (135.15 g, 376.5 mmol), Na2SO4
(38.18 g, 268.9 mmol), K2CO3 (37.11 g, 268.9 mmol), Cu (5.13 g, 80.7 mmol) and nitrobenzene were obtained using the Sub 1-1 synthesis method of Example 1, to obtain 71.88 g (yield: 63%) of the product.
(4) (4)
SubSub
1-7 1-7
합성예Synthesis Example
<반응식 6><Scheme 6>
출발물질인 2,3-diphenyl-1H-indole (61.54 g, 228.5 mmol)에 Sub 1-I-1 (114.83 g, 319.9 mmol), Na2SO4
(32.45 g, 228.5 mmol), K2CO3
(31.53 g, 228.5 mmol), Cu (4.36 g, 68.6 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-1 합성법을 사용하여 생성물 67.47 g (수율: 59%)를 얻었다.Starting material 2,3-diphenyl-1H-indole (61.54 g, 228.5 mmol) in Sub 1-I-1 (114.83 g, 319.9 mmol), Na2SO4
(32.45 g, 228.5 mmol), K2CO3
(31.53 g, 228.5 mmol), Cu (4.36 g, 68.6 mmol) and nitrobenzene were obtained using the Sub 1-1 synthesis method of Example 1, to obtain 67.47 g (yield: 59%) of the product.
(5) (5)
SubSub
1-9 1-9
합성예Synthesis Example
<반응식 7>Scheme 7
출발물질인 1H-benzo[g]indole (55.36 g, 331.1 mmol)에 Sub 1-I-1 (166.4 g, 463.5 mmol), Na2SO4
(47.02 g, 331.1 mmol), K2CO3 (45.69 g, 331.1 mmol), Cu (6.31 g, 99.3 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-1 합성법을 사용하여 생성물 76.49 g (수율: 58%)를 얻었다.Starting material 1H-benzo [g] indole (55.36 g, 331.1 mmol) in Sub 1-I-1 (166.4 g, 463.5 mmol), Na2SO4
(47.02 g, 331.1 mmol), K2CO3 (45.69 g, 331.1 mmol), Cu (6.31 g, 99.3 mmol) and nitrobenzene were obtained using the Sub 1-1 synthesis method of Example 1, to obtain 76.49 g (yield: 58%) of the product.
(6) (6)
SubSub
1-10 1-10
합성예Synthesis Example
<반응식 8>Scheme 8
출발물질인 1H-dibenzo[e,g]indole (58.77 g, 270.5 mmol)에 Sub 1-I-1 (135.95 g, 378.7 mmol), Na2SO4 (38.41 g, 270.5 mmol), K2CO3 (37.33 g, 270.5 mmol), Cu (5.16 g, 81.2 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-1 합성법을 사용하여 생성물 67.92 g (수율: 56%)를 얻었다.Starting material, 1 H -dibenzo [ e , g ] indole (58.77 g, 270.5 mmol), Sub 1-I-1 (135.95 g, 378.7 mmol), Na 2 SO 4 (38.41 g, 270.5 mmol), K 2 CO 3 (37.33 g, 270.5 mmol), Cu (5.16 g, 81.2 mmol) and nitrobenzene were obtained using the Sub 1-1 synthesis method of Example 1, to obtain 67.92 g (yield: 56%) of the product.
(7) (7)
SubSub
1-11 1-11
합성예Synthesis Example
<반응식 9>Scheme 9
출발물질인 1H-indole (40.17 g, 342.9 mmol)에 Sub 1-I-2 (191.57 g, 480.1 mmol), Na2SO4 (48.69 g, 342.9 mmol), K2CO3 (47.32 g, 342.9 mmol), Cu (6.54 g, 102.9 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-1 합성법을 사용하여 생성물 82.55 g (수율: 62%)를 얻었다.Starting material 1 H -indole (40.17 g, 342.9 mmol), Sub 1-I-2 (191.57 g, 480.1 mmol), Na 2 SO 4 (48.69 g, 342.9 mmol), K 2 CO 3 (47.32 g, 342.9 mmol), Cu (6.54 g, 102.9 mmol) and nitrobenzene were obtained using the Sub 1-1 synthesis method of Example 1, to obtain 82.55 g (yield: 62%) of the product.
(8) (8)
SubSub
1-12 1-12
합성예Synthesis Example
<반응식 10>Scheme 10
출발물질인 5-phenyl-1H-indole (46.23 g, 239.2 mmol)에 Sub 1-I-2 (133.66 g, 334.9 mmol), Na2SO4
(33.97 g, 239.2 mmol), K2CO3 (33.01 g, 239.2 mmol), Cu (4.56 g, 71.8 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-1 합성법을 사용하여 생성물 63.32 g (수율: 57%)를 얻었다.Starting material 5-phenyl-1H-indole (46.23 g, 239.2 mmol) in Sub 1-I-2 (133.66 g, 334.9 mmol), Na2SO4
(33.97 g, 239.2 mmol), K2CO3 (33.01 g, 239.2 mmol), Cu (4.56 g, 71.8 mmol) and nitrobenzene were obtained using 63.32 g (yield: 57%) of the product using the Sub 1-1 synthesis method of Example 1.
(9) (9)
SubSub
1-13 1-13
합성예Synthesis Example
<반응식 11>Scheme 11
출발물질인 2-phenyl-1H-indole (49.92 g, 258.3 mmol)에 Sub 1-I-2 (144.32 g, 361.7 mmol), Na2SO4
(36.68 g, 258.3 mmol), K2CO3 (35.65 g, 258.3 mmol), Cu (4.92 g, 77.5 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-1 합성법을 사용하여 생성물 75.57 g (수율: 63%)를 얻었다.Starting material 2-phenyl-1H-indole (49.92 g, 258.3 mmol) to Sub 1-I-2 (144.32 g, 361.7 mmol), Na2SO4
(36.68 g, 258.3 mmol), K2CO3 (35.65 g, 258.3 mmol), Cu (4.92 g, 77.5 mmol) and nitrobenzene were obtained using the Sub 1-1 synthesis method of Example 1, to obtain 75.57 g (yield: 63%) of the product.
(10) 10
SubSub
1-14 1-14
합성예Synthesis Example
<반응식 12>Scheme 12
출발물질인 2,3-diphenyl-1H-indole (47.13 g, 175 mmol)에 Sub 1-I-2 (97.77 g, 245 mmol), Na2SO4
(24.85 g, 175 mmol), K2CO3
(24.15 g, 175 mmol), Cu (3.34 g, 52.5 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-1 합성법을 사용하여 생성물 49.18 g (수율: 52%)를 얻었다.Starting material 2,3-diphenyl-1H-indole (47.13 g, 175 mmol) in Sub 1-I-2 (97.77 g, 245 mmol), Na2SO4
(24.85 g, 175 mmol), K2CO3
(24.15 g, 175 mmol), Cu (3.34 g, 52.5 mmol) and nitrobenzene were used to give 49.18 g (yield: 52%) of the product using the Sub 1-1 synthesis method of Example 1.
(11) (11)
SubSub
1-15 1-15
합성예Synthesis Example
<반응식 13>Scheme 13
출발물질인 3H-benzo[e]indole (48.79 g, 291.8 mmol)에 Sub 1-I-2 (163.02 g, 408.5 mmol), Na2SO4
(41.43 g, 291.8 mmol), K2CO3 (40.27 g, 291.8 mmol), Cu (5.56 g, 87.5 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-1 합성법을 사용하여 생성물 60.11 g (수율: 47%)를 얻었다.Starting material 3H-benzo [e] indole (48.79 g, 291.8 mmol) in Sub 1-I-2 (163.02 g, 408.5 mmol), Na2SO4
(41.43 g, 291.8 mmol), K2CO3 (40.27 g, 291.8 mmol), Cu (5.56 g, 87.5 mmol) and nitrobenzene were obtained using the Sub 1-1 synthesis method of Example 1, to obtain 60.11 g (yield: 47%) of the product.
(12) (12)
SubSub
1-19 1-19
합성예Synthesis Example
<반응식 14>Scheme 14
출발물질인 5-phenyl-1H-indole (40.17 g, 208.3 mmol)에 Sub 1-I-3 (152.61 g, 291.7 mmol), Na2SO4
(29.58 g, 208.3 mmol), K2CO3 (28.75 g, 208.3 mmol), Cu (3.97 g, 62.5 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-1 합성법을 사용하여 생성물 74.78 g (수율: 61%)를 얻었다.Starting material 5-phenyl-1H-indole (40.17 g, 208.3 mmol) in Sub 1-I-3 (152.61 g, 291.7 mmol), Na2SO4
(29.58 g, 208.3 mmol), K2CO3 (28.75 g, 208.3 mmol), Cu (3.97 g, 62.5 mmol) and nitrobenzene were obtained using the Sub 1-1 synthesis method of Example 1, yielding 74.78 g (yield: 61%) of the product.
(13) (13)
SubSub
1-25 1-25
합성예Synthesis Example
<반응식 15>Scheme 15
출발물질인 1H-indole (39.94 g, 340.9 mmol)에 Sub 1-I-4 (248.76 g, 477.3 mmol), Na2SO4 (48.41 g, 340.9 mmol), K2CO3 (47.04 g, 340.9 mmol), Cu (6.5 g, 102.3 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-1 합성법을 사용하여 생성물 92.22 g (수율: 53%)를 얻었다.Starting material 1 H -indole (39.94 g, 340.9 mmol) in Sub 1-I-4 (248.76 g, 477.3 mmol), Na 2 SO 4 (48.41 g, 340.9 mmol), K 2 CO 3 (47.04 g, 340.9 mmol), Cu (6.5 g, 102.3 mmol) and nitrobenzene were obtained using the Sub 1-1 synthesis method of Example 1 to obtain 92.22 g (yield: 53%) of the product.
Sub 1-I의 예시는 아래와 같으나, 이에 한정되는 것은 아니다.Examples of Sub 1-I are as follows, but are not limited thereto.
한편, Sub 1의 예시는 아래와 같으나, 이에 한정되는 것은 아니며, 이들의 FD-MS는 하기 표 1과 같다.Meanwhile, examples of Sub 1 are as follows, but are not limited thereto, and their FD-MSs are shown in Table 1 below.
표 1
Table 1
| 화합물 | FD-MS | 화합물 | FD-MS |
| Sub 1-1 | m/z=347.03(C20H14BrN=348.24) | Sub 1-2 | m/z=365.02(C20H13BrFN=366.23) |
| Sub 1-3 | m/z=423.06(C26H18BrN=424.33) | Sub 1-4 | m/z=424.06(C25H17BrN2=425.32) |
| Sub 1-5 | m/z=423.06(C26H18BrN=424.33) | Sub 1-6 | m/z=514.10(C32H23BrN2=515.44) |
| Sub 1-7 | m/z= 499.09(C32H22BrN=500.43) | Sub 1-8 | m/z=397.05(C24H16BrN=398.29) |
| Sub 1-9 | m/z=397.05(C24H16BrN=398.29) | Sub 1-10 | m/z=447.06(C28H18BrN=448.35) |
| Sub 1-11 | m/z=387.06(C23H18BrN=388.30) | Sub 1-12 | m/z=463.09(C29H22BrN=464.40) |
| Sub 1-13 | m/z=463.09(C29H22BrN=464.40) | Sub 1-14 | m/z=539.12(C35H26BrN=540.49) |
| Sub 1-15 | m/z=437.08(C27H20BrN=438.36) | Sub 1-16 | m/z=437.08(C27H20BrN=438.36) |
| Sub 1-17 | m/z=487.09(C31H22BrN=488.42) | Sub 1-18 | m/z=511.09(C33H22BrN=512.44) |
| Sub 1-19 | m/z=587.12(C39H26BrN=588.53) | Sub 1-20 | m/z=587.12(C39H26BrN=588.53) |
| Sub 1-21 | m/z=663.16(C45H30BrN=664.63) | Sub 1-22 | m/z=561.11(C37H24BrN=562.50) |
| Sub 1-23 | m/z=561.11(C37H24BrN=562.50) | Sub 1-24 | m/z=611.12(C41H26BrN=612.56) |
| Sub 1-25 | m/z=509.08(C33H20BrN=510.42) | Sub 1-26 | m/z=585.11(C39H24BrN=586.52) |
| Sub 1-27 | m/z=585.11(C39H24BrN=586.52) | Sub 1-28 | m/z=661.14(C45H28BrN=662.61) |
| compound | FD-MS | compound | FD-MS |
| Sub 1-1 | m / z = 347.03 (C 20 H 14 BrN = 348.24) | Sub 1-2 | m / z = 365.02 (C 20 H 13 BrFN = 366.23) |
| Sub 1-3 | m / z = 423.06 (C 26 H 18 BrN = 424.33) | Sub 1-4 | m / z = 424.06 (C 25 H 17 BrN 2 = 425.32) |
| Sub 1-5 | m / z = 423.06 (C 26 H 18 BrN = 424.33) | Sub 1-6 | m / z = 514.10 (C 32 H 23 BrN 2 = 515.44) |
| Sub 1-7 | m / z = 499.09 (C 32 H 22 BrN = 500.43) | Sub 1-8 | m / z = 397.05 (C 24 H 16 BrN = 398.29) |
| Sub 1-9 | m / z = 397.05 (C 24 H 16 BrN = 398.29) | Sub 1-10 | m / z = 447.06 (C 28 H 18 BrN = 448.35) |
| Sub 1-11 | m / z = 387.06 (C 23 H 18 BrN = 388.30) | Sub 1-12 | m / z = 463.09 (C 29 H 22 BrN = 464.40) |
| Sub 1-13 | m / z = 463.09 (C 29 H 22 BrN = 464.40) | Sub 1-14 | m / z = 539.12 (C 35 H 26 BrN = 540.49) |
| Sub 1-15 | m / z = 437.08 (C 27 H 20 BrN = 438.36) | Sub 1-16 | m / z = 437.08 (C 27 H 20 BrN = 438.36) |
| Sub 1-17 | m / z = 487.09 (C 31 H 22 BrN = 488.42) | Sub 1-18 | m / z = 511.09 (C 33 H 22 BrN = 512.44) |
| Sub 1-19 | m / z = 587.12 (C 39 H 26 BrN = 588.53) | Sub 1-20 | m / z = 587.12 (C 39 H 26 BrN = 588.53) |
| Sub 1-21 | m / z = 663.16 (C 45 H 30 BrN = 664.63) | Sub 1-22 | m / z = 561.11 (C 37 H 24 BrN = 562.50) |
| Sub 1-23 | m / z = 561.11 (C 37 H 24 BrN = 562.50) | Sub 1-24 | m / z = 611.12 (C 41 H 26 BrN = 612.56) |
| Sub 1-25 | m / z = 509.08 (C 33 H 20 BrN = 510.42) | Sub 1-26 | m / z = 585.11 (C 39 H 24 BrN = 586.52) |
| Sub 1-27 | m / z = 585.11 (C 39 H 24 BrN = 586.52) | Sub 1-28 | m / z = 661.14 (C 45 H 28 BrN = 662.61) |
[실시예 2] Example 2
SubSub
2의 합성 2, synthesis
반응식 1의 Sub 2는 하기 반응식 16의 반응경로에 의해 합성될 수 있다.Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 16 below.
<반응식 16>Scheme 16
Sub 2에 속하는 구체적 화합물의 합성예는 다음과 같다.Synthesis examples of specific compounds belonging to Sub 2 are as follows.
(1) (One)
SubSub
2-11 2-11
합성예Synthesis Example
<반응식 17>Scheme 17
출발물질인 bromobenzene (24.18 g, 154.3 mmol)을 둥근바닥플라스크에 toluene으로 녹인 후에, naphthalen-2-amine (44.18 g, 308.6 mmol), Pd2(dba)3 (4.24 g, 4.63 mmol), 50% P(t-Bu)3 (4.5ml, 9.26 mmol), NaOt-Bu (44.49 g, 462.9 mmol)을 첨가하고 40℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축한 후 생성된 화합물을 silicagel column 및 재결정하여 생성물 27.69 g (수율: 82%)를 얻었다.After starting bromobenzene (24.18 g, 154.3 mmol) was dissolved in toluene in a round bottom flask, naphthalen-2-amine (44.18 g, 308.6 mmol), Pd 2 (dba) 3 (4.24 g, 4.63 mmol), 50% P ( t -Bu) 3 (4.5 ml, 9.26 mmol), NaO t -Bu (44.49 g, 462.9 mmol) were added and stirred at 40 ° C. After the reaction was completed, the mixture was extracted with CH 2 Cl 2 and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting compound was purified by silicagel column and recrystallized to give 27.69 g (yield: 82%) of the product.
(2) (2)
SubSub
2-18 2-18
합성예Synthesis Example
<반응식 18>Scheme 18
상기 합성에서 얻어진 4-bromo-1,1'-biphenyl (51.46 g, 220.7 mmol)에 [1,1'-biphenyl]-4-amine (74.71 g, 441.5 mmol), Pd2(dba)3 (6.06g, 6.6 mmol), 50% P(t-Bu)3 (6.5ml, 13.2 mmol), NaOt-Bu (63.63 g, 662.1 mmol), toluene을 상기 실시예 2의 Sub 2-11 합성법을 사용하여 생성물 56.75 g (수율: 80%)를 얻었다.[1,1'-biphenyl] -4-amine (74.71 g, 441.5 mmol), Pd 2 (dba) 3 (6.06) to 4-bromo-1,1'-biphenyl (51.46 g, 220.7 mmol) obtained in the above synthesis. g, 6.6 mmol), 50% P ( t -Bu) 3 (6.5ml, 13.2 mmol), NaO t -Bu (63.63 g, 662.1 mmol), toluene were prepared using the Sub 2-11 synthesis of Example 2 above. 56.75 g (yield: 80%) of the product were obtained.
(3) (3)
SubSub
2-29 2-29
합성예Synthesis Example
<반응식 19>Scheme 19
상기 합성에서 얻어진 2-bromo-9,9-dimethyl-9H-fluorene (40.24 g, 147 mmol)에 [1,1'-biphenyl]-4-amine (49.86 g, 295 mmol), Pd2(dba)3 (4.04 g, 4.4 mmol), 50% P(t-Bu)3 (4.3ml, 8.8 mmol), NaOt-Bu (42.38 g, 441 mmol), toluene을 상기 실시예 2의 Sub 2-11 합성법을 사용하여 생성물 38.26 g (수율: 72%)를 얻었다.To 2-bromo-9,9-dimethyl-9 H -fluorene (40.24 g, 147 mmol) obtained in the above synthesis, [1,1'-biphenyl] -4-amine (49.86 g, 295 mmol), Pd 2 (dba ) 3 (4.04 g, 4.4 mmol), 50% P ( t -Bu) 3 (4.3ml, 8.8 mmol), NaO t -Bu (42.38 g, 441 mmol), toluene Synthesis gave 38.26 g (yield: 72%) of product.
(4) (4)
SubSub
2-33 2-33
합성예Synthesis Example
<반응식 20>Scheme 20
상기 합성에서 얻어진 2-bromo-9,9-diphenyl-9H-fluorene (38.93 g, 98 mmol)에 [1,1'-biphenyl]-4-amine (33.16 g, 196 mmol), Pd2(dba)3 (2.66 g, 2.9 mmol), 50% P(t-Bu)3 (2.9ml, 5.9 mmol), NaOt-Bu (28.26 g, 294 mmol), toluene을 상기 실시예 2의 Sub 2-11 합성법을 사용하여 생성물 32.36 g (수율: 68%)를 얻었다.To 2-bromo-9,9-diphenyl-9 H -fluorene (38.93 g, 98 mmol) obtained in the above synthesis, [1,1'-biphenyl] -4-amine (33.16 g, 196 mmol), Pd 2 (dba ) 3 (2.66 g, 2.9 mmol), 50% P ( t -Bu) 3 (2.9ml, 5.9 mmol), NaO t -Bu (28.26 g, 294 mmol), toluene Synthesis gave 32.36 g (yield: 68%) of product.
(5) (5)
SubSub
2-43 2-43
합성예Synthesis Example
<반응식 21>Scheme 21
상기 합성에서 얻어진 4-bromodibenzo[b,d]thiophene (41.56 g, 157.9 mmol)에 [1,1'-biphenyl]-4-amine (53.45 g, 315.9 mmol), Pd2(dba)3 (4.34 g, 4.7 mmol), 50% P(t-Bu)3 (4.6ml, 9.5 mmol), NaOt-Bu (45.53 g, 473.7 mmol), toluene을 상기 실시예 2의 Sub 2-11 합성법을 사용하여 생성물 43.29 g (수율: 78%)를 얻었다.[1,1'-biphenyl] -4-amine (53.45 g, 315.9 mmol), Pd 2 (dba) 3 (4.34 g) to 4-bromodibenzo [ b , d ] thiophene (41.56 g, 157.9 mmol) obtained in the above synthesis. , 4.7 mmol), 50% P ( t -Bu) 3 (4.6ml, 9.5 mmol), NaO t -Bu (45.53 g, 473.7 mmol), toluene were obtained using the Sub 2-11 synthesis of Example 2 above. 43.29 g (yield: 78%) were obtained.
(6) (6)
SubSub
2-47 2-47
합성예Synthesis Example
<반응식 22>Scheme 22
상기 합성에서 얻어진 2-bromodibenzo[b,d]furan (32.41 g, 131.2 mmol)에 dibenzo[b,d]furan-2-amine (48.06 g, 262 mmol), Pd2(dba)3 (3.6 g, 3.9 mmol), 50% P(t-Bu)3 (3.8ml, 7.9 mmol), NaOt-Bu (37.83 g, 393.6 mmol), toluene을 상기 실시예 2의 Sub 2-11 합성법을 사용하여 생성물 29.34 g (수율: 64%)를 얻었다.2-bromodibenzo [ b , d ] furan (32.41 g, 131.2 mmol) obtained in the above synthesis was converted to dibenzo [ b , d ] furan-2-amine (48.06 g, 262 mmol), Pd 2 (dba) 3 (3.6 g, 3.9 mmol), 50% P ( t -Bu) 3 (3.8ml, 7.9 mmol), NaO t -Bu (37.83 g, 393.6 mmol), toluene were obtained using the Sub 2-11 synthesis of Example 2, and the product was 29.34 g (yield: 64%) was obtained.
한편, Sub 2의 예시는 아래와 같으나, 이에 한정되는 것은 아니며, 이들의 FD-MS는 하기 표 2와 같다.Meanwhile, examples of Sub 2 are as follows, but are not limited thereto, and their FD-MSs are shown in Table 2 below.
표 2
TABLE 2
| 화합물 | FD-MS | 화합물 | FD-MS |
| Sub 2-1 | m/z=169.09(C12H11N=169.22) | Sub 2-2 | m/z=187.08(C12H10FN=187.21) |
| Sub 2-3 | m/z=209.12(C15H15N=209.29) | Sub 2-4 | m/z=205.07(C12H9F2N=205.20) |
| Sub 2-5 | m/z=227.11(C15H14FN=227.28) | Sub 2-6 | m/z=249.15(C18H19N=249.35) |
| Sub 2-7 | m/z=219.10(C16H13N=219.28) | Sub 2-8 | m/z=237.10(C16H12FN=237.27) |
| Sub 2-9 | m/z=259.14(C19H17N=259.34) | Sub 2-10 | m/z=295.14(C22H17N=295.38) |
| Sub 2-11 | m/z=219.10(C16H13N=219.28) | Sub 2-12 | m/z=237.10(C16H12FN=237.27) |
| Sub 2-13 | m/z=259.14(C19H17N=259.34) | Sub 2-14 | m/z=295.14(C22H17N=295.38) |
| Sub 2-15 | m/z=269.12(C20H15N=269.34) | Sub 2-16 | m/z=269.12(C20H15N=269.34) |
| Sub 2-17 | m/z=269.12(C20H15N=269.34) | Sub 2-18 | m/z=321.15(C24H19N=321.41) |
| Sub 2-19 | m/z=245.12(C18H15N=245.32) | Sub 2-20 | m/z=263.11(C18H14FN=263.31) |
| Sub 2-21 | m/z=285.15(C21H19N=285.38) | Sub 2-22 | m/z=321.15(C24H19N=321.41) |
| Sub 2-23 | m/z=397.18(C30H23N=397.51) | Sub 2-24 | m/z=335.17(C25H21N=335.44) |
| Sub 2-25 | m/z=335.17(C25H21N=335.44) | Sub 2-26 | m/z=303.14(C21H18FN=303.37) |
| Sub 2-27 | m/z=325.18(C24H23N=325.45) | Sub 2-28 | m/z=285.15(C21H19N=285.38) |
| Sub 2-29 | m/z=361.18(C27H23N=361.48) | Sub 2-30 | m/z=401.21(C30H27N=401.54) |
| Sub 2-31 | m/z=409.18(C31H23N=409.52) | Sub 2-32 | m/z=459.20(C35H25N=459.58) |
| Sub 2-33 | m/z=485.21(C37H27N=485.62) | Sub 2-34 | m/z=407.17(C31H21N=407.51) |
| Sub 2-35 | m/z=483.20(C37H25N=483.60) | Sub 2-36 | m/z=391.14(C27H21NS=391.53) |
| Sub 2-37 | m/z=325.09(C22H15NS=325.43) | Sub 2-38 | m/z=325.09(C22H15NS=325.43) |
| Sub 2-39 | m/z=293.07(C18H12FNS=293.36) | Sub 2-40 | m/z=315.11(C21H17NS=315.43) |
| Sub 2-41 | m/z=275.08(C18H13NS=275.37) | Sub 2-42 | m/z=351.11(C24H17NS=351.46) |
| Sub 2-43 | m/z=351.11(C24H17NS=351.46) | Sub 2-44 | m/z=410.18(C30H22N2=410.51) |
| Sub 2-45 | m/z=381.06(C24H15NS2=381.51) | Sub 2-46 | m/z=381.06(C24H15NS2=381.51) |
| Sub 2-47 | m/z=349.11(C24H15NO2=349.38) |
| compound | FD-MS | compound | FD-MS |
| Sub 2-1 | m / z = 169.09 (C 12 H 11 N = 169.22) | Sub 2-2 | m / z = 187.08 (C 12 H 10 FN = 187.21) |
| Sub 2-3 | m / z = 209.12 (C 15 H 15 N = 209.29) | Sub 2-4 | m / z = 205.07 (C 12 H 9 F 2 N = 205.20) |
| Sub 2-5 | m / z = 227.11 (C 15 H 14 FN = 227.28) | Sub 2-6 | m / z = 249.15 (C 18 H 19 N = 249.35) |
| Sub 2-7 | m / z = 219.10 (C 16 H 13 N = 219.28) | Sub 2-8 | m / z = 237.10 (C 16 H 12 FN = 237.27) |
| Sub 2-9 | m / z = 259.14 (C 19 H 17 N = 259.34) | Sub 2-10 | m / z = 295.14 (C 22 H 17 N = 295.38) |
| Sub 2-11 | m / z = 219.10 (C 16 H 13 N = 219.28) | Sub 2-12 | m / z = 237.10 (C 16 H 12 FN = 237.27) |
| Sub 2-13 | m / z = 259.14 (C 19 H 17 N = 259.34) | Sub 2-14 | m / z = 295.14 (C 22 H 17 N = 295.38) |
| Sub 2-15 | m / z = 269.12 (C 20 H 15 N = 269.34) | Sub 2-16 | m / z = 269.12 (C 20 H 15 N = 269.34) |
| Sub 2-17 | m / z = 269.12 (C 20 H 15 N = 269.34) | Sub 2-18 | m / z = 321.15 (C 24 H 19 N = 321.41) |
| Sub 2-19 | m / z = 245.12 (C 18 H 15 N = 245.32) | Sub 2-20 | m / z = 263.11 (C 18 H 14 FN = 263.31) |
| Sub 2-21 | m / z = 285.15 (C 21 H 19 N = 285.38) | Sub 2-22 | m / z = 321.15 (C 24 H 19 N = 321.41) |
| Sub 2-23 | m / z = 397.18 (C 30 H 23 N = 397.51) | Sub 2-24 | m / z = 335.17 (C 25 H 21 N = 335.44) |
| Sub 2-25 | m / z = 335.17 (C 25 H 21 N = 335.44) | Sub 2-26 | m / z = 303.14 (C 21 H 18 FN = 303.37) |
| Sub 2-27 | m / z = 325.18 (C 24 H 23 N = 325.45) | Sub 2-28 | m / z = 285.15 (C 21 H 19 N = 285.38) |
| Sub 2-29 | m / z = 361.18 (C 27 H 23 N = 361.48) | Sub 2-30 | m / z = 401.21 (C 30 H 27 N = 401.54) |
| Sub 2-31 | m / z = 409.18 (C 31 H 23 N = 409.52) | Sub 2-32 | m / z = 459.20 (C 35 H 25 N = 459.58) |
| Sub 2-33 | m / z = 485.21 (C 37 H 27 N = 485.62) | Sub 2-34 | m / z = 407.17 (C 31 H 21 N = 407.51) |
| Sub 2-35 | m / z = 483.20 (C 37 H 25 N = 483.60) | Sub 2-36 | m / z = 391.14 (C 27 H 21 NS = 391.53) |
| Sub 2-37 | m / z = 325.09 (C 22 H 15 NS = 325.43) | Sub 2-38 | m / z = 325.09 (C 22 H 15 NS = 325.43) |
| Sub 2-39 | m / z = 293.07 (C 18 H 12 FNS = 293.36) | Sub 2-40 | m / z = 315.11 (C 21 H 17 NS = 315.43) |
| Sub 2-41 | m / z = 275.08 (C 18 H 13 NS = 275.37) | Sub 2-42 | m / z = 351.11 (C 24 H 17 NS = 351.46) |
| Sub 2-43 | m / z = 351.11 (C 24 H 17 NS = 351.46) | Sub 2-44 | m / z = 410.18 (C 30 H 22 N 2 = 410.51) |
| Sub 2-45 | m / z = 381.06 (C 24 H 15 NS 2 = 381.51) | Sub 2-46 | m / z = 381.06 (C 24 H 15 NS 2 = 381.51) |
| Sub 2-47 | m / z = 349.11 (C 24 H 15 NO 2 = 349.38) |
[실시예 3]Example 3
ProductProduct
의 합성Synthesis of
Sub 2 (1 당량)을 둥근바닥플라스크에 toluene으로 녹인 후에, Sub 1 (1.2 당량), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.08 당량), NaOt-Bu (3 당량)을 첨가하고 100°C에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축한 후 생성된 화합물을 silicagel column 및 재결정하여 Final products를 얻었다.Sub 2 (1 equiv) was dissolved in toluene in a round bottom flask, then Sub 1 (1.2 equiv), Pd 2 (dba) 3 (0.03 equiv), P ( t -Bu) 3 (0.08 equiv), NaO t -Bu (3 equiv) was added and stirred at 100 ° C. After completion of the reaction, the mixture was extracted with CH 2 Cl 2 and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting compound was purified by silicagel column and recrystallization to obtain final products.
(1) (One)
ProductProduct
1-1 1-1
합성예Synthesis Example
<반응식 23>Scheme 23
상기 합성에서 얻어진 Sub 2-29 (7.5 g, 20.8 mmol)을 둥근바닥플라스크에 toluene으로 녹인 후에, Sub 1-5 (10.57 g, 24.9 mmol), Pd2(dba)3 (0.57 g, 0.6 mmol), 50% P(t-Bu)3 (0.8ml, 1.7 mmol), NaOt-Bu (6 g, 62.4 mmol)을 첨가하고 100℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축한 후 생성된 화합물을 silicagel column 및 재결정하여 생성물 11.88 g (수율: 81%)를 얻었다.Sub 2-29 (7.5 g, 20.8 mmol) obtained in the above synthesis was dissolved in toluene in a round bottom flask, and then Sub 1-5 (10.57 g, 24.9 mmol), Pd 2 (dba) 3 (0.57 g, 0.6 mmol) , 50% P ( t- Bu) 3 (0.8 ml, 1.7 mmol), NaO t -Bu (6 g, 62.4 mmol) was added and stirred at 100 ° C. After the reaction was completed, the mixture was extracted with CH 2 Cl 2 and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting compound was purified by silicagel column and recrystallized to give the product 11.88 g (yield: 81%).
(2) (2)
ProductProduct
1-2 1-2
합성예Synthesis Example
<반응식 24>Scheme 24
상기 합성에서 얻어진 Sub 2-18 (7.71 g, 24 mmol)에 Sub 1-5 (12.22 g, 28.8 mmol), Pd2(dba)3 (0.64 g, 0.7 mmol), 50% P(t-Bu)3 (0.9ml, 1.9 mmol), NaOt-Bu (6.92 g, 72 mmol), toluene을 상기 실시예 3의 Product 1-1 합성법을 사용하여 생성물 11.81 g (수율: 74%)를 얻었다.Sub 2-18 (7.71 g, 24 mmol) obtained in the above synthesis in Sub 1-5 (12.22 g, 28.8 mmol), Pd 2 (dba) 3 (0.64 g, 0.7 mmol), 50% P ( t -Bu) 3 (0.9 ml, 1.9 mmol), NaO t -Bu (6.92 g, 72 mmol) and toluene were obtained using the Product 1-1 synthesis method of Example 3, to obtain 11.81 g (yield: 74%) of the product.
(3) (3)
ProductProduct
1-4 1-4
합성예Synthesis Example
<반응식 25>Scheme 25
상기 합성에서 얻어진 Sub 2-18 (7.29 g, 22.7 mmol)에 Sub 1-7 (13.62 g, 27.2 mmol), Pd2(dba)3 (0.62 g, 0.7 mmol), 50% P(t-Bu)3 (0.9ml, 1.8 mmol), NaOt-Bu (6.55 g, 68.1 mmol), toluene을 상기 실시예 3의 Product 1-1 합성법을 사용하여 생성물 12.11 g (수율: 72%)를 얻었다.Sub 2-18 (7.29 g, 22.7 mmol) obtained in the above synthesis in Sub 1-7 (13.62 g, 27.2 mmol), Pd 2 (dba) 3 (0.62 g, 0.7 mmol), 50% P ( t -Bu) 3 (0.9 ml, 1.8 mmol), NaO t -Bu (6.55 g, 68.1 mmol) and toluene were obtained using the Product 1-1 synthesis method of Example 3 to obtain 12.11 g (yield: 72%).
(4) (4)
ProductProduct
1-5 1-5
합성예Synthesis Example
<반응식 26>Scheme 26
상기 합성에서 얻어진 Sub 2-29 (8.21 g, 22.7 mmol)에 Sub 1-3 (11.58 g, 27.3 mmol), Pd2(dba)3 (0.62 g, 0.7 mmol), 50% P(t-Bu)3 (0.9ml, 1.8 mmol), NaOt-Bu (6.55 g, 68.1 mmol), toluene을 상기 실시예 3의 Product 1-1 합성법을 사용하여 생성물 12 g (수율: 75%)를 얻었다.Sub 2-29 (8.21 g, 22.7 mmol) obtained in the above synthesis to Sub 1-3 (11.58 g, 27.3 mmol), Pd 2 (dba) 3 (0.62 g, 0.7 mmol), 50% P ( t -Bu) 3 (0.9 ml, 1.8 mmol), NaO t -Bu (6.55 g, 68.1 mmol) and toluene were obtained using the Product 1-1 synthesis method of Example 3, to obtain 12 g (yield: 75%) of the product.
(5) (5)
ProductProduct
1-6 1-6
합성예Synthesis Example
<반응식 27>Scheme 27
상기 합성에서 얻어진 Sub 2-18 (10.37 g, 32.3 mmol)에 Sub 1-3 (16.43 g, 38.7 mmol), Pd2(dba)3 (0.89 g, 1 mmol), 50% P(t-Bu)3 (1.3ml, 2.6 mmol), NaOt-Bu (9.31 g, 96.3 mmol), toluene을 상기 실시예 3의 Product 1-1 합성법을 사용하여 생성물 17.6 g (수율: 82%)를 얻었다.Sub 2-18 (10.37 g, 32.3 mmol) obtained in the above synthesis to Sub 1-3 (16.43 g, 38.7 mmol), Pd 2 (dba) 3 (0.89 g, 1 mmol), 50% P ( t -Bu) 3 (1.3 ml, 2.6 mmol), NaO t -Bu (9.31 g, 96.3 mmol) and toluene were obtained using the Product 1-1 synthesis method of Example 3 to obtain 17.6 g (yield: 82%) of the product.
(6) (6)
ProductProduct
1-13 1-13
합성예Synthesis Example
<반응식 28>Scheme 28
상기 합성에서 얻어진 Sub 2-18 (8.46 g, 26.3 mmol)에 Sub 1-11 (12.26 g, 31.6 mmol), Pd2(dba)3 (0.72 g, 0.8 mmol), 50% P(t-Bu)3 (1ml, 2.1 mmol), NaOt-Bu (7.58 g, 78.9 mmol), toluene을 상기 실시예 3의 Product 1-1 합성법을 사용하여 생성물 13.06 g (수율: 79%)를 얻었다.Sub 2-18 (8.46 g, 26.3 mmol) obtained in the above synthesis in Sub 1-11 (12.26 g, 31.6 mmol), Pd 2 (dba) 3 (0.72 g, 0.8 mmol), 50% P ( t -Bu) 3 (1 ml, 2.1 mmol), NaO t -Bu (7.58 g, 78.9 mmol) and toluene were obtained using 13.06 g (yield: 79%) of the product using the Product 1-1 synthesis method of Example 3.
(7) (7)
ProductProduct
1-14 1-14
합성예Synthesis Example
<반응식 29>Scheme 29
상기 합성에서 얻어진 Sub 2-18 (8.46 g, 26.3 mmol)에 Sub 1-12 (14.67 g, 31.6 mmol), Pd2(dba)3 (0.72 g, 0.8 mmol), 50% P(t-Bu)3 (1ml, 2.1 mmol), NaOt-Bu (7.58 g, 78.9 mmol), toluene을 상기 실시예 3의 Product 1-1 합성법을 사용하여 생성물 14.27 g (수율: 77%)를 얻었다.Sub 2-18 (8.46 g, 26.3 mmol) obtained in the above synthesis to Sub 1-12 (14.67 g, 31.6 mmol), Pd 2 (dba) 3 (0.72 g, 0.8 mmol), 50% P ( t -Bu) 3 (1 ml, 2.1 mmol), NaO t -Bu (7.58 g, 78.9 mmol) and toluene were obtained using 14.27 g (yield: 77%) of the product using the Product 1-1 synthesis method of Example 3.
(8) (8)
ProductProduct
1-15 1-15
합성예Synthesis Example
<반응식 30>Scheme 30
상기 합성에서 얻어진 Sub 2-18 (11.84 g, 36.8 mmol)에 Sub 1-19 (26.02 g, 44.2 mmol), Pd2(dba)3 (1.01 g, 1.1 mmol), 50% P(t-Bu)3 (1.4ml, 2.9 mmol), NaOt-Bu (10.61 g, 110.4 mmol), toluene을 상기 실시예 3의 Product 1-1 합성법을 사용하여 생성물 20.44 g (수율: 67%)를 얻었다.Sub 2-18 (11.84 g, 36.8 mmol) obtained in the above synthesis in Sub 1-19 (26.02 g, 44.2 mmol), Pd 2 (dba) 3 (1.01 g, 1.1 mmol), 50% P ( t -Bu) 3 (1.4 ml, 2.9 mmol), NaO t -Bu (10.61 g, 110.4 mmol) and toluene were obtained using the Product 1-1 synthesis method of Example 3 to obtain 20.44 g (yield: 67%) of the product.
(9) (9)
ProductProduct
1-17 1-17
합성예Synthesis Example
<반응식 31>Scheme 31
상기 합성에서 얻어진 Sub 2-43 (8.33 g, 23.7 mmol)에 Sub 1-1 (9.9 g, 28.4 mmol), Pd2(dba)3 (0.65 g, 0.7 mmol), 50% P(t-Bu)3 (0.9ml, 1.9 mmol), NaOt-Bu (6.83 g, 71.1 mmol), toluene을 상기 실시예 3의 Product 1-1 합성법을 사용하여 생성물 11.29 g (수율: 77%)를 얻었다.To Sub 2-43 (8.33 g, 23.7 mmol) obtained in the above synthesis Sub 1-1 (9.9 g, 28.4 mmol), Pd 2 (dba) 3 (0.65 g, 0.7 mmol), 50% P ( t -Bu) 3 (0.9 ml, 1.9 mmol), NaO t -Bu (6.83 g, 71.1 mmol) and toluene were obtained using 11.29 g (yield: 77%) of the product using the Product 1-1 synthesis method of Example 3.
(10) 10
ProductProduct
1-20 1-20
합성예Synthesis Example
<반응식 32>Scheme 32
상기 합성에서 얻어진 Sub 2-47 (9.81 g, 28.1 mmol)에 Sub 1-25 (17.2 g, 33.7 mmol), Pd2(dba)3 (0.77 g, 0.8 mmol), 50% P(t-Bu)3 (1.1ml, 2.3 mmol), NaOt-Bu (8.1 g, 84.3 mmol), toluene을 상기 실시예 3의 Product 1-1 합성법을 사용하여 생성물 18.17 g (수율: 83%)를 얻었다.To Sub 2-47 (9.81 g, 28.1 mmol) obtained in the above synthesis Sub 1-25 (17.2 g, 33.7 mmol), Pd 2 (dba) 3 (0.77 g, 0.8 mmol), 50% P ( t -Bu) 3 (1.1 ml, 2.3 mmol), NaO t -Bu (8.1 g, 84.3 mmol) and toluene were obtained using the Product 1-1 synthesis method of Example 3 to obtain 18.17 g (yield: 83%) of the product.
(11) (11)
ProductProduct
1-96 1-96
합성예Synthesis Example
<반응식 33>Scheme 33
상기 합성에서 얻어진 Sub 2-11 (7.02 g, 32 mmol)에 Sub 1-13 (17.84 g, 38.4 mmol), Pd2(dba)3 (0.88 g, 1 mmol), 50% P(t-Bu)3 (1.3ml, 2.6 mmol), NaOt-Bu (9.23 g, 96 mmol), toluene을 상기 실시예 3의 Product 1-1 합성법을 사용하여 생성물 13.31 g (수율: 69%)를 얻었다.Sub 2-11 (7.02 g, 32 mmol) obtained in the above synthesis in Sub 1-13 (17.84 g, 38.4 mmol), Pd 2 (dba) 3 (0.88 g, 1 mmol), 50% P ( t -Bu) 3 (1.3 ml, 2.6 mmol), NaO t -Bu (9.23 g, 96 mmol) and toluene were obtained using the Product 1-1 synthesis method of Example 3, to obtain 13.31 g (yield: 69%) of the product.
(12) (12)
ProductProduct
1-112 1-112
합성예Synthesis Example
<반응식 34>Scheme 34
상기 합성에서 얻어진 Sub 2-18 (7.17 g, 22.3 mmol)에 Sub 1-14 (14.47 g, 26.8 mmol), Pd2(dba)3 (0.61 g, 0.7 mmol), 50% P(t-Bu)3 (0.9ml, 1.8 mmol), NaOt-Bu (6.43 g, 66.9 mmol), toluene을 상기 실시예 3의 Product 1-1 합성법을 사용하여 생성물 11.15 g (수율: 64%)를 얻었다.Sub 2-18 (7.17 g, 22.3 mmol) obtained in the above synthesis to Sub 1-14 (14.47 g, 26.8 mmol), Pd 2 (dba) 3 (0.61 g, 0.7 mmol), 50% P ( t -Bu) 3 (0.9 ml, 1.8 mmol), NaO t -Bu (6.43 g, 66.9 mmol) and toluene were obtained using the Product 1-1 synthesis method of Example 3, to obtain 11.15 g (yield: 64%) of the product.
(13) (13)
ProductProduct
1-127 1-127
합성예Synthesis Example
<반응식 35>Scheme 35
상기 합성에서 얻어진 Sub 2-18 (7.05 g, 21.9 mmol)에 Sub 1-15 (11.54 g, 26.3 mmol), Pd2(dba)3 (0.6 g, 0.7 mmol), 50% P(t-Bu)3 (0.9ml, 1.8 mmol), NaOt-Bu (6.31 g, 65.7 mmol), toluene을 상기 실시예 3의 Product 1-1 합성법을 사용하여 생성물 10.56 g (수율: 71%)를 얻었다.Sub 2-18 (7.05 g, 21.9 mmol) obtained in the above synthesis in Sub 1-15 (11.54 g, 26.3 mmol), Pd 2 (dba) 3 (0.6 g, 0.7 mmol), 50% P ( t -Bu) 3 (0.9 ml, 1.8 mmol), NaO t -Bu (6.31 g, 65.7 mmol) and toluene were obtained using the Product 1-1 synthesis method of Example 3, to obtain 10.56 g (yield: 71%) of the product.
(14) (14)
ProductProduct
1-135 1-135
합성예Synthesis Example
<반응식 36>Scheme 36
상기 합성에서 얻어진 Sub 2-33 (7.22 g, 14.9 mmol)에 Sub 1-9 (7.11 g, 17.8 mmol), Pd2(dba)3 (0.41 g, 0.5 mmol), 50% P(t-Bu)3 (0.6ml, 1.2 mmol), NaOt-Bu (4.3 g, 44.7 mmol), toluene을 상기 실시예 3의 Product 1-1 합성법을 사용하여 생성물 9.93 g (수율: 83%)를 얻었다.Sub 2-33 (7.22 g, 14.9 mmol) obtained in the above synthesis in Sub 1-9 (7.11 g, 17.8 mmol), Pd 2 (dba) 3 (0.41 g, 0.5 mmol), 50% P ( t -Bu) 3 (0.6 ml, 1.2 mmol), NaO t -Bu (4.3 g, 44.7 mmol) and toluene were obtained using the Product 1-1 synthesis method of Example 3 to obtain 9.93 g (yield: 83%) of the product.
(15) (15)
ProductProduct
1-142 1-142
합성예Synthesis Example
<반응식 37>Scheme 37
상기 합성에서 얻어진 Sub 2-18 (8.24 g, 25.6 mmol)에 Sub 1-10 (13.8 g, 30.8 mmol), Pd2(dba)3 (0.71 g, 0.8 mmol), 50% P(t-Bu)3 (1ml, 2.1 mmol), NaOt-Bu (7.38 g, 76.8 mmol), toluene을 상기 실시예 3의 Product 1-1 합성법을 사용하여 생성물 13.4 g (수율: 76%)를 얻었다.Sub 2-18 (8.24 g, 25.6 mmol) obtained in the above synthesis in Sub 1-10 (13.8 g, 30.8 mmol), Pd 2 (dba) 3 (0.71 g, 0.8 mmol), 50% P ( t -Bu) 3 (1 ml, 2.1 mmol), NaO t -Bu (7.38 g, 76.8 mmol) and toluene were obtained using the Product 1-1 synthesis method of Example 3, to obtain 13.4 g (yield: 76%) of the product.
한편, 상기와 같은 합성예에 따라 제조된 본 발명의 화합물 1-1 ~ 1-150의 FD-MS 값은 하기 표 3과 같다.On the other hand, FD-MS values of the compounds 1-1 to 1-150 of the present invention prepared according to the synthesis examples as described above are shown in Table 3.
표 3
TABLE 3
| 화합물 | FD-MS | 화합물 | FD-MS |
| 1-1 | m/z=704.32(C53H40N2=704.90) | 1-2 | m/z=664.29(C50H36N2=664.83) |
| 1-3 | m/z=740.32(C56H40N2=740.93) | 1-4 | m/z=740.32(C56H40N2=740.93) |
| 1-5 | m/z=704.32(C53H40N2=704.90) | 1-6 | m/z=664.29(C50H36N2=664.83) |
| 1-7 | m/z=588.26(C44H32N2=588.74) | 1-8 | m/z= 664.29(C50H36N2=664.83) |
| 1-9 | m/z=752.32(C57H40N2=752.94) | 1-10 | m/z=750.30(C57H38N2=750.93) |
| 1-11 | m/z=676.29(C51H36N2=676.84) | 1-12 | m/z=674.27(C51H34N2=674.83) |
| 1-13 | m/z=628.29(C47H36N2=628.80) | 1-14 | m/z=704.32(C53H40N2=704.90) |
| 1-15 | m/z=828.35(C63H44N2=829.04) | 1-16 | m/z=752.32(C57H40N2=752.94) |
| 1-17 | m/z=618.21(C44H30N2S=618.79) | 1-18 | m/z=648.17(C44H28N2S2=648.84) |
| 1-19 | m/z=793.35(C59H43N3=793.99) | 1-20 | m/z=778.26(C57H34N2O2=778.89) |
| 1-21 | m/z=436.19(C32H24N2=436.55) | 1-22 | m/z=486.21(C36H26N2=486.61) |
| 1-23 | m/z=486.21(C36H26N2=486.61) | 1-24 | m/z=512.23C38H28N2=512.64) |
| 1-25 | m/z=542.18(C38H26N2S=542.69) | 1-26 | m/z=552.26(C41H32N2=552.71) |
| 1-27 | m/z=454.18(C32H23FN2=454.54) | 1-28 | m/z=476.23(C35H28N2=476.61) |
| 1-29 | m/z=536.23(C40H28N2=536.66) | 1-30 | m/z=536.23(C40H28N2=536.66) |
| 1-31 | m/z=562.24(C42H30N2=562.70) | 1-32 | m/z=592.20(C42H28N2S=592.75) |
| 1-33 | m/z=602.27(C45H34N2=602.76) | 1-34 | m/z=504.20(C36H25FN2=504.60) |
| 1-35 | m/z=526.24(C39H30N2=526.67) | 1-36 | m/z=536.23(C40H28N2=536.66) |
| 1-37 | m/z=562.24(C42H30N2=562.70) | 1-38 | m/z=592.20(C42H28N2S=592.75) |
| 1-39 | m/z=602.27(C45H34N2=602.76) | 1-40 | m/z=504.20(C36H25FN2=504.60) |
| 1-41 | m/z=526.24(C39H30N2=526.67) | 1-42 | m/z=588.26(C44H32N2=588.74) |
| 1-43 | m/z=618.21(C44H30N2S=618.79) | 1-44 | m/z=628.29(C47H36N2=628.80) |
| 1-45 | m/z=530.22(C38H27FN2=530.63) | 1-46 | m/z=552.26(C41H32N2=552.71) |
| 1-47 | m/z=648.17(C44H28N2S2=648.84) | 1-48 | m/z=658.24(C47H34N2S=658.85) |
| 1-49 | m/z=560.17(C38H25FN2S=560.68) | 1-50 | m/z=582.21(C41H30N2S=582.76) |
| 1-51 | m/z=668.32(C50H40N2=668.87) | 1-52 | m/z=570.25(C41H31FN2=570.70) |
| 1-53 | m/z=592.29(C44H36N2=592.77) | 1-54 | m/z=472.18(C32H22F2N2=472.53) |
| 1-55 | m/z=494.22(C35H27FN2=494.60) | 1-56 | m/z=516.26(C38H32N2=516.67) |
| 1-57 | m/z=454.18(C32H23FN2=454.54) | 1-58 | m/z=512.23(C38H28N2=512.64) |
| 1-59 | m/z=513.22(C37H27N3=513.63) | 1-60 | m/z=603.27(C44H33N3=603.75) |
| 1-61 | m/z=726.30(C55H38N2=726.90) | 1-62 | m/z=552.26(C41H32N2=552.71) |
| 1-63 | m/z=602.27(C45H34N2=602.76) | 1-64 | m/z=526.24(C39H30N2=526.67) |
| 1-65 | m/z=676.29(C51H36N2=676.84) | 1-66 | m/z=726.30(C55H38N2=726.90) |
| 1-67 | m/z=650.27(C49H34N2=650.81) | 1-68 | m/z=750.30(C57H38N2=750.93) |
| 1-69 | m/z=674.27(C51H34N2=674.83) | 1-70 | m/z=724.29(C55H36N2=724.89) |
| 1-71 | m/z=648.26(C49H32N2=648.79) | 1-72 | m/z=828.35(C63H44N2=829.04) |
| 1-73 | m/z=638.27(C48H34N2=638.80) | 1-74 | m/z=562.24(C42H30N2=562.70) |
| 1-75 | m/z=802.33(C61H42N2=803.00) | 1-76 | m/z=678.30(C51H38N2=678.86) |
| 1-77 | m/z=628.29(C47H36N2=628.80) | 1-78 | m/z=678.30(C51H38N2=678.86) |
| 1-79 | m/z=602.27(C45H34N2=602.76) | 1-80 | m/z=726.30(C55H38N2=726.90) |
| 1-81 | m/z=752.32(C57H40N2=752.94) | 1-82 | m/z=802.33(C61H42N2=803.00) |
| 1-83 | m/z=826.33(C63H42N2=827.02) | 1-84 | m/z=750.30(C57H38N2=750.93) |
| 1-85 | m/z=800.32(C61H40N2=800.98) | 1-86 | m/z=724.29(C55H36N2=724.89) |
| 1-87 | m/z=588.26(C44H32N2=588.74) | 1-88 | m/z=828.35(C63H44N2=829.04) |
| 1-89 | m/z=638.27(C48H34N2=638.80) | 1-90 | m/z=562.24(C42H30N2=562.70) |
| 1-91 | m/z=802.33(C61H42N2=803.00) | 1-92 | m/z=678.30(C51H38N2=678.86) |
| 1-93 | m/z=704.32(C53H40N2=704.90) | 1-94 | m/z=628.29(C47H36N2=628.80) |
| 1-95 | m/z=678.30(C51H38N2=678.86) | 1-96 | m/z=602.27(C45H34N2=602.76) |
| 1-97 | m/z=828.35(C63H44N2=829.04) | 1-98 | m/z=752.32(C57H40N2=752.94) |
| 1-99 | m/z=802.33(C61H42N2=803.00) | 1-100 | m/z=726.30(C55H38N2=726.90) |
| 1-101 | m/z=826.33(C63H42N2=827.02) | 1-102 | m/z=750.30(C57H38N2=750.93) |
| 1-103 | m/z=800.32(C61H40N2=800.98) | 1-104 | m/z=724.29(C55H36N2=724.89) |
| 1-105 | m/z=714.30(C54H38N2=714.89) | 1-106 | m/z=664.29(C50H36N2=664.83) |
| 1-107 | m/z=780.35(C59H44N2=780.99) | 1-108 | m/z=904.38(C69H48N2=905.13) |
| 1-109 | m/z=638.27(C48H34N2=638.80) | 1-110 | m/z=878.37(C67H46N2=879.10) |
| 1-111 | m/z=754.33(C57H42N2=754.96) | 1-112 | m/z=780.35(C59H44N2=780.99) |
| 1-113 | m/z=828.35(C63H44N2=829.04) | 1-114 | m/z=704.32(C53H40N2=704.90) |
| 1-115 | m/z=754.33(C57H42N2=754.96) | 1-116 | m/z=678.30(C51H38N2=678.86) |
| 1-117 | m/z=904.38(C69H48N2=905.13) | 1-118 | m/z=826.33(C63H42N2=827.02) |
| 1-119 | m/z=878.37(C67H46N2=879.10) | 1-120 | m/z=802.33(C61H42N2=803.00) |
| 1-121 | m/z=902.37(C69H46N2=903.12) | 1-122 | m/z=876.35(C67H44N2=877.08) |
| 1-123 | m/z=800.32(C61H40N2=800.98) | 1-124 | m/z=638.27(C48H34N2=638.80) |
| 1-125 | m/z=678.30(C51H38N2=678.86) | 1-126 | m/z=802.33(C61H42N2=803.00) |
| 1-127 | m/z=678.30(C51H38N2=678.86) | 1-128 | m/z=718.33(C54H42N2=718.92) |
| 1-129 | m/z=842.37(C64H46N2=843.06) | 1-130 | m/z=802.33(C61H42N2=803.00) |
| 1-131 | m/z=842.37(C64H46N2=843.06) | 1-132 | m/z=966.40(C74H50N2=967.20) |
| 1-133 | m/z=638.27(C48H34N2=638.80) | 1-134 | m/z=678.30(C51H38N2=678.86) |
| 1-135 | m/z=802.33(C61H42N2=803.00) | 1-136 | m/z=678.30(C51H38N2=678.86) |
| 1-137 | m/z=718.33(C54H42N2=718.92) | 1-138 | m/z=842.37(C64H46N2=843.06) |
| 1-139 | m/z=802.33(C61H42N2=803.00) | 1-140 | m/z=842.37(C64H46N2=843.06) |
| 1-141 | m/z=966.40(C74H50N2=967.20) | 1-142 | m/z=688.29(C52H36N2=688.86) |
| 1-143 | m/z=728.32(C55H40N2=728.92) | 1-144 | m/z=852.35(C65H44N2=853.06) |
| 1-145 | m/z=728.32(C55H40N2=728.92) | 1-146 | m/z=768.35(C58H44N2=768.98) |
| 1-147 | m/z=892.38(C68H48N2=893.12) | 1-148 | m/z=852.35(C65H44N2=853.06) |
| 1-149 | m/z=892.38(C68H48N2=893.12) | 1-150 | m/z=1016.41(C78H52N2=1017.26) |
| compound | FD-MS | compound | FD-MS |
| 1-1 | m / z = 704.32 (C 53 H 40 N 2 = 704.90) | 1-2 | m / z = 664.29 (C 50 H 36 N 2 = 664.83) |
| 1-3 | m / z = 740.32 (C 56 H 40 N 2 = 740.93) | 1-4 | m / z = 740.32 (C 56 H 40 N 2 = 740.93) |
| 1-5 | m / z = 704.32 (C 53 H 40 N 2 = 704.90) | 1-6 | m / z = 664.29 (C 50 H 36 N 2 = 664.83) |
| 1-7 | m / z = 588.26 (C 44 H 32 N 2 = 588.74) | 1-8 | m / z = 664.29 (C 50 H 36 N 2 = 664.83) |
| 1-9 | m / z = 752.32 (C 57 H 40 N 2 = 752.94) | 1-10 | m / z = 750.30 (C 57 H 38 N 2 = 750.93) |
| 1-11 | m / z = 676.29 (C 51 H 36 N 2 = 676.84) | 1-12 | m / z = 674.27 (C 51 H 34 N 2 = 674.83) |
| 1-13 | m / z = 628.29 (C 47 H 36 N 2 = 628.80) | 1-14 | m / z = 704.32 (C 53 H 40 N 2 = 704.90) |
| 1-15 | m / z = 828.35 (C 63 H 44 N 2 = 829.04) | 1-16 | m / z = 752.32 (C 57 H 40 N 2 = 752.94) |
| 1-17 | m / z = 618.21 (C 44 H 30 N 2 S = 618.79) | 1-18 | m / z = 648.17 (C 44 H 28 N 2 S 2 = 648.84) |
| 1-19 | m / z = 793.35 (C 59 H 43 N 3 = 793.99) | 1-20 | m / z = 778.26 (C 57 H 34 N 2 O 2 = 778.89) |
| 1-21 | m / z = 436.19 (C 32 H 24 N 2 = 436.55) | 1-22 | m / z = 486.21 (C 36 H 26 N 2 = 486.61) |
| 1-23 | m / z = 486.21 (C 36 H 26 N 2 = 486.61) | 1-24 | m / z = 512.23 C 38 H 28 N 2 = 512.64) |
| 1-25 | m / z = 542.18 (C 38 H 26 N 2 S = 542.69) | 1-26 | m / z = 552.26 (C 41 H 32 N 2 = 552.71) |
| 1-27 | m / z = 454.18 (C 32 H 23 FN 2 = 454.54) | 1-28 | m / z = 476.23 (C 35 H 28 N 2 = 476.61) |
| 1-29 | m / z = 536.23 (C 40 H 28 N 2 = 536.66) | 1-30 | m / z = 536.23 (C 40 H 28 N 2 = 536.66) |
| 1-31 | m / z = 562.24 (C 42 H 30 N 2 = 562.70) | 1-32 | m / z = 592.20 (C 42 H 28 N 2 S = 592.75) |
| 1-33 | m / z = 602.27 (C 45 H 34 N 2 = 602.76) | 1-34 | m / z = 504.20 (C 36 H 25 FN 2 = 504.60) |
| 1-35 | m / z = 526.24 (C 39 H 30 N 2 = 526.67) | 1-36 | m / z = 536.23 (C 40 H 28 N 2 = 536.66) |
| 1-37 | m / z = 562.24 (C 42 H 30 N 2 = 562.70) | 1-38 | m / z = 592.20 (C 42 H 28 N 2 S = 592.75) |
| 1-39 | m / z = 602.27 (C 45 H 34 N 2 = 602.76) | 1-40 | m / z = 504.20 (C 36 H 25 FN 2 = 504.60) |
| 1-41 | m / z = 526.24 (C 39 H 30 N 2 = 526.67) | 1-42 | m / z = 588.26 (C 44 H 32 N 2 = 588.74) |
| 1-43 | m / z = 618.21 (C 44 H 30 N 2 S = 618.79) | 1-44 | m / z = 628.29 (C 47 H 36 N 2 = 628.80) |
| 1-45 | m / z = 530.22 (C 38 H 27 FN 2 = 530.63) | 1-46 | m / z = 552.26 (C 41 H 32 N 2 = 552.71) |
| 1-47 | m / z = 648.17 (C 44 H 28 N 2 S 2 = 648.84) | 1-48 | m / z = 658.24 (C 47 H 34 N 2 S = 658.85) |
| 1-49 | m / z = 560.17 (C 38 H 25 FN 2 S = 560.68) | 1-50 | m / z = 582.21 (C 41 H 30 N 2 S = 582.76) |
| 1-51 | m / z = 668.32 (C 50 H 40 N 2 = 668.87) | 1-52 | m / z = 570.25 (C 41 H 31 FN 2 = 570.70) |
| 1-53 | m / z = 592.29 (C 44 H 36 N 2 = 592.77) | 1-54 | m / z = 472.18 (C 32 H 22 F 2 N 2 = 472.53) |
| 1-55 | m / z = 494.22 (C 35 H 27 FN 2 = 494.60) | 1-56 | m / z = 516.26 (C 38 H 32 N 2 = 516.67) |
| 1-57 | m / z = 454.18 (C 32 H 23 FN 2 = 454.54) | 1-58 | m / z = 512.23 (C 38 H 28 N 2 = 512.64) |
| 1-59 | m / z = 513.22 (C 37 H 27 N 3 = 513.63) | 1-60 | m / z = 603.27 (C 44 H 33 N 3 = 603.75) |
| 1-61 | m / z = 726.30 (C 55 H 38 N 2 = 726.90) | 1-62 | m / z = 552.26 (C 41 H 32 N 2 = 552.71) |
| 1-63 | m / z = 602.27 (C 45 H 34 N 2 = 602.76) | 1-64 | m / z = 526.24 (C 39 H 30 N 2 = 526.67) |
| 1-65 | m / z = 676.29 (C 51 H 36 N 2 = 676.84) | 1-66 | m / z = 726.30 (C 55 H 38 N 2 = 726.90) |
| 1-67 | m / z = 650.27 (C 49 H 34 N 2 = 650.81) | 1-68 | m / z = 750.30 (C 57 H 38 N 2 = 750.93) |
| 1-69 | m / z = 674.27 (C 51 H 34 N 2 = 674.83) | 1-70 | m / z = 724.29 (C 55 H 36 N 2 = 724.89) |
| 1-71 | m / z = 648.26 (C 49 H 32 N 2 = 648.79) | 1-72 | m / z = 828.35 (C 63 H 44 N 2 = 829.04) |
| 1-73 | m / z = 638.27 (C 48 H 34 N 2 = 638.80) | 1-74 | m / z = 562.24 (C 42 H 30 N 2 = 562.70) |
| 1-75 | m / z = 802.33 (C 61 H 42 N 2 = 803.00) | 1-76 | m / z = 678.30 (C 51 H 38 N 2 = 678.86) |
| 1-77 | m / z = 628.29 (C 47 H 36 N 2 = 628.80) | 1-78 | m / z = 678.30 (C 51 H 38 N 2 = 678.86) |
| 1-79 | m / z = 602.27 (C 45 H 34 N 2 = 602.76) | 1-80 | m / z = 726.30 (C 55 H 38 N 2 = 726.90) |
| 1-81 | m / z = 752.32 (C 57 H 40 N 2 = 752.94) | 1-82 | m / z = 802.33 (C 61 H 42 N 2 = 803.00) |
| 1-83 | m / z = 826.33 (C 63 H 42 N 2 = 827.02) | 1-84 | m / z = 750.30 (C 57 H 38 N 2 = 750.93) |
| 1-85 | m / z = 800.32 (C 61 H 40 N 2 = 800.98) | 1-86 | m / z = 724.29 (C 55 H 36 N 2 = 724.89) |
| 1-87 | m / z = 588.26 (C 44 H 32 N 2 = 588.74) | 1-88 | m / z = 828.35 (C 63 H 44 N 2 = 829.04) |
| 1-89 | m / z = 638.27 (C 48 H 34 N 2 = 638.80) | 1-90 | m / z = 562.24 (C 42 H 30 N 2 = 562.70) |
| 1-91 | m / z = 802.33 (C 61 H 42 N 2 = 803.00) | 1-92 | m / z = 678.30 (C 51 H 38 N 2 = 678.86) |
| 1-93 | m / z = 704.32 (C 53 H 40 N 2 = 704.90) | 1-94 | m / z = 628.29 (C 47 H 36 N 2 = 628.80) |
| 1-95 | m / z = 678.30 (C 51 H 38 N 2 = 678.86) | 1-96 | m / z = 602.27 (C 45 H 34 N 2 = 602.76) |
| 1-97 | m / z = 828.35 (C 63 H 44 N 2 = 829.04) | 1-98 | m / z = 752.32 (C 57 H 40 N 2 = 752.94) |
| 1-99 | m / z = 802.33 (C 61 H 42 N 2 = 803.00) | 1-100 | m / z = 726.30 (C 55 H 38 N 2 = 726.90) |
| 1-101 | m / z = 826.33 (C 63 H 42 N 2 = 827.02) | 1-102 | m / z = 750.30 (C 57 H 38 N 2 = 750.93) |
| 1-103 | m / z = 800.32 (C 61 H 40 N 2 = 800.98) | 1-104 | m / z = 724.29 (C 55 H 36 N 2 = 724.89) |
| 1-105 | m / z = 714.30 (C 54 H 38 N 2 = 714.89) | 1-106 | m / z = 664.29 (C 50 H 36 N 2 = 664.83) |
| 1-107 | m / z = 780.35 (C 59 H 44 N 2 = 780.99) | 1-108 | m / z = 904.38 (C 69 H 48 N 2 = 905.13) |
| 1-109 | m / z = 638.27 (C 48 H 34 N 2 = 638.80) | 1-110 | m / z = 878.37 (C 67 H 46 N 2 = 879.10) |
| 1-111 | m / z = 754.33 (C 57 H 42 N 2 = 754.96) | 1-112 | m / z = 780.35 (C 59 H 44 N 2 = 780.99) |
| 1-113 | m / z = 828.35 (C 63 H 44 N 2 = 829.04) | 1-114 | m / z = 704.32 (C 53 H 40 N 2 = 704.90) |
| 1-115 | m / z = 754.33 (C 57 H 42 N 2 = 754.96) | 1-116 | m / z = 678.30 (C 51 H 38 N 2 = 678.86) |
| 1-117 | m / z = 904.38 (C 69 H 48 N 2 = 905.13) | 1-118 | m / z = 826.33 (C 63 H 42 N 2 = 827.02) |
| 1-119 | m / z = 878.37 (C 67 H 46 N 2 = 879.10) | 1-120 | m / z = 802.33 (C 61 H 42 N 2 = 803.00) |
| 1-121 | m / z = 902.37 (C 69 H 46 N 2 = 903.12) | 1-122 | m / z = 876.35 (C 67 H 44 N 2 = 877.08) |
| 1-123 | m / z = 800.32 (C 61 H 40 N 2 = 800.98) | 1-124 | m / z = 638.27 (C 48 H 34 N 2 = 638.80) |
| 1-125 | m / z = 678.30 (C 51 H 38 N 2 = 678.86) | 1-126 | m / z = 802.33 (C 61 H 42 N 2 = 803.00) |
| 1-127 | m / z = 678.30 (C 51 H 38 N 2 = 678.86) | 1-128 | m / z = 718.33 (C 54 H 42 N 2 = 718.92) |
| 1-129 | m / z = 842.37 (C 64 H 46 N 2 = 843.06) | 1-130 | m / z = 802.33 (C 61 H 42 N 2 = 803.00) |
| 1-131 | m / z = 842.37 (C 64 H 46 N 2 = 843.06) | 1-132 | m / z = 966.40 (C 74 H 50 N 2 = 967.20) |
| 1-133 | m / z = 638.27 (C 48 H 34 N 2 = 638.80) | 1-134 | m / z = 678.30 (C 51 H 38 N 2 = 678.86) |
| 1-135 | m / z = 802.33 (C 61 H 42 N 2 = 803.00) | 1-136 | m / z = 678.30 (C 51 H 38 N 2 = 678.86) |
| 1-137 | m / z = 718.33 (C 54 H 42 N 2 = 718.92) | 1-138 | m / z = 842.37 (C 64 H 46 N 2 = 843.06) |
| 1-139 | m / z = 802.33 (C 61 H 42 N 2 = 803.00) | 1-140 | m / z = 842.37 (C 64 H 46 N 2 = 843.06) |
| 1-141 | m / z = 966.40 (C 74 H 50 N 2 = 967.20) | 1-142 | m / z = 688.29 (C 52 H 36 N 2 = 688.86) |
| 1-143 | m / z = 728.32 (C 55 H 40 N 2 = 728.92) | 1-144 | m / z = 852.35 (C 65 H 44 N 2 = 853.06) |
| 1-145 | m / z = 728.32 (C 55 H 40 N 2 = 728.92) | 1-146 | m / z = 768.35 (C 58 H 44 N 2 = 768.98) |
| 1-147 | m / z = 892.38 (C 68 H 48 N 2 = 893.12) | 1-148 | m / z = 852.35 (C 65 H 44 N 2 = 853.06) |
| 1-149 | m / z = 892.38 (C 68 H 48 N 2 = 893.12) | 1-150 | m / z = 1016.41 (C 78 H 52 N 2 = 1017.26) |
합성예Synthesis Example
2 : 화학식 2의 합성 2: Synthesis of Chemical Formula 2
<반응식 38>Scheme 38
[실시예 4] Example 4
1. One.
SubSub
3의 합성 예시 ( Example of synthesis of 3
실시예EXAMPLE
1, One,
실시예EXAMPLE
2와 동일한 실험 Same experiment as 2
methodmethod
))
<반응식 39> - Method 1 Scheme 39 -Method 1
<반응식 40> - Method 2 Scheme 40 -Method 2
(1) (One)
SubSub
3-3-1 합성 예 (L= 3-3-1 Synthesis Example (L =
biphenylbiphenyl
))
<반응식 41>Scheme 41
출발물질인 9H-carbazole (50.16 g, 300 mmol)에 4-bromo-4'-iodo-1,1'-biphenyl (129.2 g, 360 mmol), Na2SO4 (42.6 g, 300 mmol), K2CO3
(41.4 g, 300 mmol), Cu (5.72 g, 90 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-1 합성법을 사용하여 생성물 80.05 g (수율: 67%)를 얻었다.Starter 9H-carbazole (50.16 g, 300 mmol) in 4-bromo-4'-iodo-1,1'-biphenyl (129.2 g, 360 mmol), Na2SO4 (42.6 g, 300 mmol), K2CO3
(41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzene were obtained using the Sub 1-1 synthesis method of Example 1, to obtain 80.05 g (yield: 67%) of the product.
(2) (2)
SubSub
3-3-2 합성 예 (L=9,9- 3-3-2 Synthesis Example (L = 9,9-
dimethyldimethyl
-9H--9H-
fluorenefluorene
))
<반응식 42>Scheme 42
출발물질인 9H-carbazole (50.16 g, 300 mmol)에 2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol), Na2SO4
(42.6 g, 300 mmol), K2CO3
(41.4 g, 300 mmol), Cu (5.72 g, 90 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-11 합성법을 사용하여 생성물 88.11 g (수율: 67%)를 얻었다Starting material 9H-carbazole (50.16 g, 300 mmol) in 2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol), Na2SO4
(42.6 g, 300 mmol), K2CO3
(41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzene were obtained using the Sub 1-11 synthesis method of Example 1 to obtain 88.11 g (yield: 67%) of the product.
(3) (3)
SubSub
3-5-1 합성 예 (L=9,9- 3-5-1 Synthesis Example (L = 9,9-
dimethyldimethyl
-9H--9H-
fluorenefluorene
))
<반응식 43>Scheme 43
출발물질인 7H-benzo[c]carbazole (65.18 g, 300 mmol)에 4-bromo-4'-iodo-1,1'-biphenyl (129.2 g, 360 mmol), Na2SO4
(42.6 g, 300 mmol), K2CO3
(41.4 g, 300 mmol), Cu (5.72 g, 90 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-1 합성법을 사용하여 생성물 92.8 g (수율: 69%)를 얻었다.In the starting material 7H-benzo [c] carbazole (65.18 g, 300 mmol), 4-bromo-4'-iodo-1,1'-biphenyl (129.2 g, 360 mmol), Na2SO4
(42.6 g, 300 mmol), K2CO3
(41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzene were obtained using the Sub 1-1 synthesis method of Example 1 to give 92.8 g (yield: 69%) of the product.
(4) (4)
SubSub
3-5-2 합성 예 (L=9,9- 3-5-2 Synthesis Example (L = 9,9-
dimethyldimethyl
-9H--9H-
fluorenefluorene
))
<반응식 44>Scheme 44
출발물질인 7H-benzo[c]carbazole (65.18 g, 300 mmol)에 2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol), Na2SO4
(42.6 g, 300 mmol), K2CO3
(41.4 g, 300 mmol), Cu (5.72 g, 90 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-11 합성법을 사용하여 생성물 95.24 g (수율: 65%)를 얻었다.In the starting material 7H-benzo [c] carbazole (65.18 g, 300 mmol), 2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol), Na2SO4
(42.6 g, 300 mmol), K2CO3
(41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzene were obtained using the Sub 1-11 synthesis method of Example 1, to obtain 95.24 g (yield: 65%) of the product.
(5) (5)
SubSub
3-6-1 합성 예 (L= 3-6-1 Synthesis Example (L =
biphenylbiphenyl
))
<반응식 45>Scheme 45
출발물질인 11H-benzo[a]carbazole (65.18 g, 300 mmol)에 4-bromo-4'-iodo-1,1'-biphenyl (129.2 g, 360 mmol), Na2SO4
(42.6 g, 300 mmol), K2CO3
(41.4 g, 300 mmol), Cu (5.72 g, 90 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-1 합성법을 사용하여 생성물 80.05 g (수율: 62%)를 얻었다.Starter 11H-benzo [a] carbazole (65.18 g, 300 mmol) in 4-bromo-4'-iodo-1,1'-biphenyl (129.2 g, 360 mmol), Na2SO4
(42.6 g, 300 mmol), K2CO3
(41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzene were obtained using the Sub 1-1 synthesis method of Example 1, to obtain 80.05 g (yield: 62%) of the product.
(6) (6)
SubSub
3-6-2 합성 예 (L=9,9- 3-6-2 Synthesis Example (L = 9,9-
dimethyldimethyl
-9H--9H-
fluorenefluorene
))
<반응식 46>Scheme 46
출발물질인 11H-benzo[a]carbazole (65.18 g, 300 mmol)에 2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol), Na2SO4 (42.6 g, 300 mmol), K2CO3
(41.4 g, 300 mmol), Cu (5.72 g, 90 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-11 합성법을 사용하여 생성물 90.85 g (수율: 62%)를 얻었다.In the starting material 11H-benzo [a] carbazole (65.18 g, 300 mmol), 2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol), Na2SO4 (42.6 g, 300 mmol), K2CO3
(41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzene were obtained using the Sub 1-11 synthesis of Example 1 to obtain 90.85 g (yield: 62%) of the product.
(7) (7)
SubSub
3-7-1 합성 예 (L= 3-7-1 Synthesis Example (L =
biphenylbiphenyl
))
<반응식 47>Scheme 47
출발물질인 5H-benzo[b]carbazole (65.18 g, 300 mmol)에 4-bromo-4'-iodo-1,1'-biphenyl (129.2 g, 360 mmol), Na2SO4 (42.6 g, 300 mmol), K2CO3
(41.4 g, 300 mmol), Cu (5.72 g, 90 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-1 합성법을 사용하여 생성물 80.7 g (수율: 60%)를 얻었다.Starter, 5H-benzo [b] carbazole (65.18 g, 300 mmol), 4-bromo-4'-iodo-1,1'-biphenyl (129.2 g, 360 mmol), Na2SO4 (42.6 g, 300 mmol), K2CO3
(41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzene were obtained using the Sub 1-1 synthesis method of Example 1, to obtain 80.7 g (yield: 60%) of the product.
(8) (8)
SubSub
3-7-2 합성 예 (L=9,9- 3-7-2 Synthesis Example (L = 9,9-
dimethyldimethyl
-9H--9H-
fluorenefluorene
))
<반응식 48>Scheme 48
출발물질인 5H-benzo[b]carbazole (65.18 g, 300 mmol)에 2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol), Na2SO4 (42.6 g, 300 mmol), K2CO3
(41.4 g, 300 mmol), Cu (5.72 g, 90 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-11 합성법을 사용하여 생성물 93.78 g (수율: 64%)를 얻었다.Starter 5H-benzo [b] carbazole (65.18 g, 300 mmol) in 2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol), Na2SO4 (42.6 g, 300 mmol), K2CO3
(41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzene were obtained using the Sub 1-11 synthesis method of Example 1, to obtain 93.78 g (yield: 64%) of the product.
(9) (9)
SubSub
3-8-1 합성 예 (L= 3-8-1 Synthesis Example (L =
biphenylbiphenyl
))
<반응식 49>Scheme 49
출발물질인 9H-dibenzo[a,c]carbazole (80.2 g, 300 mmol)에 4-bromo-4'-iodo-1,1'-biphenyl (129.2 g, 360 mmol), Na2SO4
(42.6 g, 300 mmol), K2CO3 (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-1 합성법을 사용하여 생성물 98.7 g (수율: 66%)를 얻었다.In the starting material 9H-dibenzo [a, c] carbazole (80.2 g, 300 mmol), 4-bromo-4'-iodo-1,1'-biphenyl (129.2 g, 360 mmol), Na2SO4
(42.6 g, 300 mmol), K2CO3 (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzene were obtained using the Sub 1-1 synthesis method of Example 1, to obtain 98.7 g (yield: 66%) of the product.
(10) 10
SubSub
3-8-2 합성 예 (L=9,9- 3-8-2 Synthesis Example (L = 9,9-
dimethyldimethyl
-9H--9H-
fluorenefluorene
))
<반응식 50>Scheme 50
출발물질인 9H-dibenzo[a,c]carbazole (80.2 g, 300 mmol)에 2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol), Na2SO4 (42.6 g, 300 mmol), K2CO3 (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-11 합성법을 사용하여 생성물 109.8 g (수율: 68%)를 얻었다.Starting material 9H-dibenzo [a, c] carbazole (80.2 g, 300 mmol) in 2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol), Na 2 SO 4 ( 42.6 g, 300 mmol), K 2 CO 3 (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol), nitrobenzene were obtained using the Sub 1-11 synthesis method of Example 1, above 109.8 g (yield: 68 %) Was obtained.
(11) (11)
SubSub
3-9-1 합성 예 (L= 3-9-1 Synthesis Example (L =
biphenylbiphenyl
))
<반응식 51>Scheme 51
출발물질인 N-phenylnaphthalen-1-amine (65.8 g, 300 mmol)에 4-bromo-4'-iodo-1,1'-biphenyl (129.2 g, 360 mmol), Na2SO4
(42.6 g, 300 mmol), K2CO3 (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-1 합성법을 사용하여 생성물 89.2 g (수율: 66%)를 얻었다.4-bromo-4'-iodo-1,1'-biphenyl (129.2 g, 360 mmol), Na as starting material N-phenylnaphthalen-1-amine (65.8 g, 300 mmol)2SO4
(42.6 g, 300 mmol), K2CO3 (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzene were obtained using the Sub 1-1 synthesis method of Example 1, to obtain 89.2 g (yield: 66%) of the product.
(12) (12)
SubSub
3-9-2 합성 예 (L=9,9- 3-9-2 Synthesis Example (L = 9,9-
dimethyldimethyl
-9H--9H-
fluorenefluorene
))
<반응식 52>Scheme 52
출발물질인 N-phenylnaphthalen-1-amine (65.8 g, 300 mmol)에 2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol), Na2SO4 (42.6 g, 300 mmol), K2CO3 (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-11 합성법을 사용하여 생성물 97.1g (수율: 66%)를 얻었다.Starting material N-phenylnaphthalen-1-amine (65.8 g, 300 mmol), 2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol), Na 2 SO 4 (42.6 g , 300 mmol), K 2 CO 3 (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol), and nitrobenzene using the Sub 1-11 synthesis of Example 1 above, 97.1 g of a product (yield: 66%) Got.
(13) (13)
SubSub
3-10-1 합성 예 (L= 3-10-1 Synthesis Example (L =
biphenylbiphenyl
))
<반응식 53>Scheme 53
출발물질인 7H-dibenzo[c,g]carbazole (80.2 g, 300 mmol)에 4-bromo-4'-iodo-1,1'-biphenyl (129.2 g, 360 mmol), Na2SO4
(42.6 g, 300 mmol), K2CO3 (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-1 합성법을 사용하여 생성물 97.2 g (수율: 65%)를 얻었다.In the starting material 7H-dibenzo [c, g] carbazole (80.2 g, 300 mmol), 4-bromo-4'-iodo-1,1'-biphenyl (129.2 g, 360 mmol), Na2SO4
(42.6 g, 300 mmol), K2CO3 (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzene were obtained using the Sub 1-1 synthesis method of Example 1, to obtain 97.2 g (yield: 65%) of the product.
(14) (14)
SubSub
3-10-2 합성 예 (L=9,9- 3-10-2 Synthesis Example (L = 9,9-
dimethyldimethyl
-9H--9H-
fluorenefluorene
))
<반응식 54>Scheme 54
출발물질인 7H-dibenzo[c,g]carbazole (80.2 g, 300 mmol)에 2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol), Na2SO4 (42.6 g, 300 mmol), K2CO3 (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol), nitrobenzene을 상기 실시예 1의 Sub 1-11 합성법을 사용하여 생성물 98.5g (수율: 61%)를 얻었다.Starting material, 7H-dibenzo [c, g] carbazole (80.2 g, 300 mmol), 2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol), Na 2 SO 4 ( 42.6 g, 300 mmol), K 2 CO 3 (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol), and nitrobenzene were obtained using 98.5 g of the product using the Sub 1-11 synthesis of Example 1 (yield: 61 %) Was obtained.
2. 2.
SubSub
4의 합성 예시 4 Synthesis Example
<반응식 55>Scheme 55
(1) M4 -2-1 합성예 (R3=H, Ar6=Phenyl) (1) -2-1 Preparation Example M4 (R 3 = H, Ar 6 = Phenyl)
<반응식 56>Scheme 56
3-bromo-9-phenyl-9H-carbazole (45.1 g, 140 mmol) 을 DMF 980mL 에 녹인 후에, Bispinacolborate (39.1 g, 154 mmol), PdCl2(dppf) 촉매 (3.43 g, 4.2 mmol), KOAc (41.3 g, 420 mmol)을 순서대로 첨가한 후 24 시간 교반하여 보레이트 화합물을 합성한 후에, 얻어진 화합물을 silicagel column 및 재결정을 걸쳐서 분리한 후 보레이트 화합물을 35.2 g (68 %)얻었다.After dissolving 3-bromo-9-phenyl-9H-carbazole (45.1 g, 140 mmol) in 980 mL of DMF, Bispinacolborate (39.1 g, 154 mmol), PdCl 2 (dppf) catalyst (3.43 g, 4.2 mmol), KOAc ( 41.3 g, 420 mmol) was added sequentially, followed by stirring for 24 hours to synthesize the borate compound, and the obtained compound was separated through a silicagel column and recrystallization to obtain 35.2 g (68%) of the borate compound.
(2) (2)
M4M4
-2-2 -2-2
합성예Synthesis Example
( (
R3R3
=H, = H,
Ar6Ar6
==
biphenylbiphenyl
))
<반응식 57>Scheme 57
상기 M4-2-1과 동일한 실험방법을 통해서 생성물을 40 g (64%) 얻었다. 40 g (64%) of the product was obtained by the same experimental method as in M4-2-1.
(3) Sub 4-1-1 합성예 [R3=H, Ar6=Phenyl, L= biphenyl (linear)] (3) Sub 4-1-1 Synthesis Example [R3= H, Ar6= Phenyl, L = biphenyl (linear)]
<반응식 58>Scheme 58
M4-2-1 (29.5 g, 80 mmol) 을 THF 360 mL 에 녹인 후에, 4-bromo-4'-iodo-1,1'-biphenyl (30.16 g, 84 mmol), Pd(PPh3)4 (2.8 g, 2.4mmol), NaOH (9.6 g, 240mmol), 물 180 mL 을 첨가한 후, 교반, 환류시킨다. 반응이 완료되면 ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축한 후 생성된 유기물을 silicagel column 및 재결정하여 생성물을 26.56 g (70 %) 얻었다.After dissolving M4-2-1 (29.5 g, 80 mmol) in 360 mL of THF, 4-bromo-4'-iodo-1,1'-biphenyl (30.16 g, 84 mmol), Pd (PPh 3 ) 4 ( 2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol) and 180 mL of water are added, followed by stirring and reflux. After the reaction was completed, the mixture was extracted with ether and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to give 26.56 g (70%).
(4) Sub 4-1-2 합성예 [R3=H, Ar6=Phenyl, L= phenyl] (4) Sub 4-1-2 Synthesis Example [R 3 = H, Ar 6 = Phenyl, L = phenyl]
<반응식 59>Scheme 59
M4-2-1 (29.5 g, 80 mmol), THF 360 mL, 1-bromo-4-iodobenzene (23.8 g, 84 mmol), Pd(PPh3)4 (2.8 g, 2.4mmol), NaOH (9.6 g, 240mmol), 물 180 mL을 첨가한 후, 교반, 환류시킨다. 반응이 완료되면 ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축한 후 생성된 유기물을 silicagel column 및 재결정하여 생성물을 22.9 g (72 %) 얻었다.M4-2-1 (29.5 g, 80 mmol), THF 360 mL, 1-bromo-4-iodobenzene (23.8 g, 84 mmol), Pd (PPh 3 ) 4 (2.8 g, 2.4 mmol), NaOH (9.6 g , 240 mmol) and 180 mL of water are added, followed by stirring and reflux. After the reaction was completed, the mixture was extracted with ether and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to give 22.9 g (72%).
(5) Sub 4-1-3 합성예 [R3=H, Ar6=Phenyl, L= biphenyl (non-linear)] (5) Sub 4-1-3 Synthesis Example [R3= H, Ar6= Phenyl, L = biphenyl (non-linear)]
<반응식 60>Scheme 60
M4-2-1 (29.5 g, 80 mmol) 을 THF 360 mL 에 녹인 후에, 4'-bromo-3-iodo-1,1'-biphenyl (30.16 g, 84 mmol), Pd(PPh3)4 (2.8 g, 2.4mmol), NaOH (9.6 g, 240mmol), 물 180 mL을 첨가한 후, 교반, 환류시킨다. 반응이 완료되면 ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축한 후 생성된 유기물을 silicagel column 및 재결정하여 생성물을 24.7 g (65 %) 얻었다.M4-2-1 (29.5 g, 80 mmol) was dissolved in 360 mL of THF, then 4'-bromo-3-iodo-1,1'-biphenyl (30.16 g, 84 mmol), Pd (PPh 3 ) 4 ( 2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol), 180 mL of water are added, followed by stirring and reflux. After the reaction was completed, the mixture was extracted with ether and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to give 24.7 g (65%).
(6) Sub 4-2-1 합성예 [R3=H, Ar6=biphenyl, L= biphenyl (linear)] (6) Sub 4-2-1 Synthesis Example [R3= H, Ar6= biphenyl, L = biphenyl (linear)]
<반응식 61>Scheme 61
상기 합성에서 얻어진 M4-2-2 (35.63 g, 80 mmol) 을 THF 360 mL 에 녹인 후에, 4-bromo-4'-iodo-1,1'-biphenyl (30.16 g, 84 mmol), Pd(PPh3)4 (2.8 g, 2.4mmol), NaOH (9.6 g, 240mmol), 물 180 mL을 첨가한 후, 교반, 환류시킨다. 반응이 완료되면 ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축한 후 생성된 유기물을 silicagel column 및 재결정하여 생성물을 29.51 g (67 %) 얻었다.M4-2-2 (35.63 g, 80 mmol) obtained in the above synthesis was dissolved in 360 mL of THF, followed by 4-bromo-4'-iodo-1,1'-biphenyl (30.16 g, 84 mmol), Pd (PPh 3 ) 4 (2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol) and 180 mL of water are added, followed by stirring and reflux. After completion of the reaction, the mixture was extracted with ether and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to give 29.51 g (67%) of the product.
(7) Sub 4-2-2 합성예 [R3=H, Ar6=biphenyl, L= phenyl] (7) Sub 4-2-2 Synthesis Example [R3= H, Ar6= biphenyl, L = phenyl]
<반응식 62>Scheme 62
M4-2 (35.63 g, 80 mmol) 을 THF 360 mL 에 녹인 후에, 1-bromo-4-iodobenzene (23.8 g, 84 mmol), Pd(PPh3)4 (2.8 g, 2.4mmol), NaOH (9.6 g, 240mmol), 물 180 mL 을 첨가한 후, 교반, 환류시킨다. 반응이 완료되면 ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축한 후 생성된 유기물을 silicagel column 및 재결정하여 생성물을 25.05 g (66 %) 얻었다.After dissolving M4-2 (35.63 g, 80 mmol) in 360 mL of THF, 1-bromo-4-iodobenzene (23.8 g, 84 mmol), Pd (PPh 3 ) 4 (2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol) and 180 mL of water are added, followed by stirring and reflux. After completion of the reaction, the mixture was extracted with ether and water, and the organic layer was dried over MgSO 4 , concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to give 25.05 g (66%) of the product.
(8) Sub 4-2-3 합성예 [R3=H, Ar6=biphenyl, L= biphenyl (non-linear)] (8) Sub 4-2-3 Synthesis Example [R3= H, Ar6= biphenyl, L = biphenyl (non-linear)]
<반응식 63>Scheme 63
M4-2 (35.63 g, 80 mmol) 을 THF 360 mL 에 녹인 후에, 4'-bromo-3-iodo-1,1'-biphenyl (30.16 g, 84 mmol), Pd(PPh3)4 (2.8 g, 2.4mmol), NaOH (9.6 g, 240mmol), 물 180 mL을 첨가한 후, 교반, 환류시킨다. 반응이 완료되면 ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축한 후 생성된 유기물을 silicagel column 및 재결정하여 생성물을 29.95 g (68 %) 얻었다.M4-2 (35.63 g, 80 mmol) was dissolved in 360 mL of THF, then 4'-bromo-3-iodo-1,1'-biphenyl (30.16 g, 84 mmol), Pd (PPh 3 ) 4 (2.8 g , 2.4 mmol), NaOH (9.6 g, 240 mmol), 180 mL of water are added, followed by stirring and reflux. After completion of the reaction, the mixture was extracted with ether and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain 29.95 g (68%) of the product.
3. 3.
SubSub
5의 합성 예시 5 Synthesis Example
- Sub 5는 상기 sub2 와 동일한 합성법이며, 동일한 화합물 및 유사 화합물을 사용 - Sub 5 is the same as the synthesis method sub2, using the same compounds and similar compounds
[실시예 5] Example 5
ProductProduct
(3-1 ~ 10-52) 합성 예시(상기 (3-1 to 10-52) Synthesis example (above
실시예EXAMPLE
3과 동일한 실험방법) Experimental method same as 3)
Sub 3 또는 Sub 4 (1 당량)을 둥근바닥플라스크에 toluene으로 녹인 후에, Sub 5 (1.2 당량), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.08 당량), NaOt-Bu (3 당량)을 첨가하고 100℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축한 후 생성된 화합물을 silicagel column 및 재결정하여 Final products(3-1 ~ 10-52)를 얻었다. Sub 3 or Sub 4 (1 equiv) was dissolved in toluene in a round bottom flask, then Sub 5 (1.2 equiv), Pd 2 (dba) 3 (0.03 equiv), P ( t -Bu) 3 (0.08 equiv), NaO t- Bu (3 equiv) was added and stirred at 100 ° C. After completion of the reaction, the mixture was extracted with CH 2 Cl 2 and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting compound was purified by silicagel column and recrystallized to obtain Final products (3-1 ~ 10-52).
상기에서 얻은 Product 중 일부의 FD-MS 값은 하기 표 4와 같다. Some of the FD-MS values of the obtained products are shown in Table 4 below.
표 4
Table 4
| 화합물 | FD-MS | 화합물 | FD-MS |
| 3-26 | m/z=638.27 (C48H34N2=638.80) | 3-29 | m/z=678.30 (C51H38N2=678.86) |
| 3-30 | m/z=802.33 (C61H42N2=803.00) | 3-31 | m/z=800.32 (C61H40N2=800.98) |
| 3-34 | m/z=668.23 (C48H32N2S=668.85) | 3-35 | m/z=652.25 (C48H32N2O=652.78) |
| 3-36 | m/z=729.31 (C54H39N3=729.91) | 3-66 | m/z=678.30 (C51H38N2=678.86) |
| 3-68 | m/z=718.33 (C54H42N2=718.92) | 3-69 | m/z=842.37 (C64H46N2=843.06) |
| 3-70 | m/z=840.35 (C64H44N2=841.05) | 3-71 | m/z=708.26 (C51H36N2S=708.91) |
| 3-72 | m/z=692.28 (C51H36N2O=692.84) | 3-73 | m/z=769.35 (C57H43N3=769.97) |
| 4-4 | m/z=638.27 (C48H34N2=638.80) | 4-7 | m/z=652.25 (C48H32N2O=652.78) |
| 4-8 | m/z=668.23 (C48H32N2S=668.85) | 4-9 | m/z=678.30 (C51H38N2=678.86) |
| 4-10 | m/z=802.33 (C61H42N2=803.00) | 4-11 | m/z=800.32 (C61H40N2=800.98) |
| 4-27 | m/z=714.30 (C54H38N2=714.89) | 4-30 | m/z=728.28 (C54H36N2O=728.88) |
| 4-31 | m/z=744.26 (C54H36N2S=744.94) | 4-32 | m/z=754.33 (C57H42N2=754.96) |
| 4-33 | m/z=878.37 (C67H46N2=879.10) | 4-34 | m/z=876.35 (C67H44N2=877.08) |
| 4-35 | m/z=678.30 (C51H38N2=678.86) | 4-43 | m/z=714.30 (C54H38N2=714.89) |
| 4-44 | m/z=754.33 (C57H42N2=754.96) | 4-45 | m/z=878.37 (C67H46N2=879.10) |
| 4-46 | m/z=876.35 (C67H44N2=877.08) | 4-47 | m/z=744.26 (C54H36N2S=744.94) |
| 4-49 | m/z=678.30 (C51H38N2=678.86) | 4-50 | m/z=802.33 (C61H42N2=803.00) |
| 4-51 | m/z=800.32 (C61H40N2=800.98) | 4-55 | m/z=638.27 (C48H34N2=638.80) |
| 4-56 | m/z=688.29 (C52H36N2=688.86) | 4-58 | m/z=714.30 (C54H38N2=714.89) |
| 4-61 | m/z=728.28 (C54H36N2O=728.88) | 4-62 | m/z=744.26 (C54H36N2S=744.94) |
| 4-63 | m/z=754.33 (C57H42N2=754.96) | 4-64 | m/z=878.37 (C67H46N2=879.10) |
| 4-65 | m/z=876.35 (C67H44N2=877.08) | 4-66 | m/z=678.30 (C51H38N2=678.86) |
| 4-67 | m/z=802.33 (C61H42N2=803.00) | 4-68 | m/z=800.32 (C61H40N2=800.98) |
| 4-103 | m/z=754.33 (C57H42N2=754.96) | 4-104 | m/z=878.37 (C67H46N2=879.10) |
| 4-105 | m/z=876.35 (C67H44N2=877.08) | 4-106 | m/z=804.35 (C61H44N2=805.02) |
| 4-107 | m/z=928.38 (C71H48N2=929.15) | 4-108 | m/z=926.37 (C71H46N2=927.14) |
| 5-2 | m/z=586.24 (C44H30N2=586.72) | 5-4 | m/z=612.26 (C46H32N2=612.76) |
| 5-6 | m/z=642.21 (C46H30N2S=642.81) | 5-7 | m/z=626.24 (C46H32N2O=626.74) |
| 5-8 | m/z=703.30 (C52H37N3=703.87) | 5-10 | m/z=652.29 (C49H36N2=652.82) |
| 5-11 | m/z=776.32 (C59H40N2=776.96) | 5-12 | m/z=774.30 (C59H38N2=774.95) |
| 5-13 | m/z=662.27 (C50H34N2=662.82) | 5-16 | m/z=702.30 (C53H38N2=702.88) |
| 5-17 | m/z=826.33 (C63H42N2=827.02) | 5-18 | m/z=824.32 (C63H40N2=825.01) |
| 5-19 | m/z=688.29 (C52H36N2=688.86) | 5-20 | m/z=728.32 (C55H40N2=728.92) |
| 5-21 | m/z=852.35 (C65H44N2=853.06) | 5-22 | m/z=850.33 (C65H42N2=851.04) |
| 5-23 | m/z=718.24 (C52H34N2S=718.90) | 5-24 | m/z=702.27 (C52H34N2O=702.84) |
| 5-36 | m/z=692.32 (C52H40N2=692.89) | 5-37 | m/z=816.35 (C62H44N2=817.03) |
| 5-38 | m/z=814.33 (C62H42N2=815.01) | 5-39 | m/z=702.30 (C53H38N2=702.88) |
| 5-42 | m/z=742.33 (C56H42N2=742.95) | 5-43 | m/z=866.37 (C66H46N2=867.08) |
| 5-44 | m/z=864.35 (C66H44N2=865.07) | 5-45 | m/z=728.32 (C55H40N2=728.92) |
| 5-46 | m/z=768.35 (C58H44N2=768.98) | 5-47 | m/z=892.38 (C68H48N2=893.12) |
| 5-48 | m/z=890.37 (C68H46N2=891.11) | 5-49 | m/z=758.28 (C55H38N2S=758.97) |
| 5-50 | m/z=742.30 (C55H38N2O=742.90) | 6-2 | m/z=586.24 (C44H30N2=586.72) |
| 6-4 | m/z=612.26 (C46H32N2=612.76) | 6-6 | m/z=642.21 (C46H30N2S=642.81) |
| 6-7 | m/z=626.24 (C46H30N2O=626.74) | 6-8 | m/z=703.30 (C52H37N3=703.87) |
| 6-10 | m/z=652.29 (C49H36N2=652.82) | 6-11 | m/z=776.32 (C59H40N2=776.96) |
| 6-12 | m/z=774.30 (C59H38N2=774.95) | 6-13 | m/z=662.27 (C50H34N2=662.82) |
| 6-16 | m/z=702.30 (C53H38N2=702.88) | 6-17 | m/z=826.33 (C63H42N2=827.02) |
| 6-18 | m/z=824.32 (C63H40N2=825.01) | 6-19 | m/z=688.29 (C52H36N2=688.86) |
| 6-20 | m/z=728.32 (C55H40N2=728.92) | 6-21 | m/z=852.35 (C65H44N2=853.06) |
| 6-22 | m/z=850.33 (C65H42N2=851.04) | 6-23 | m/z=718.24 (C52H34N2S=718.90) |
| 6-24 | m/z=702.27 (C52H34N2O=702.84) | 6-36 | m/z=692.32 (C52H40N2=692.89) |
| 6-37 | m/z=816.35 (C62H44N2=817.03) | 6-38 | m/z=814.33 (C62H42N2=815.01) |
| 6-39 | m/z=702.30 (C53H38N2=702.88) | 6-40 | m/z=732.26 (C53H36N2S=732.93) |
| 6-41 | m/z=716.28 (C53H36N2O=716.87) | 6-42 | m/z=742.33 (C56H42N2=742.95) |
| 6-43 | m/z=866.37 (C66H46N2=867.08) | 6-44 | m/z=864.35 (C66H44N2=865.07) |
| 6-45 | m/z=728.32 (C55H40N2=728.92) | 6-46 | m/z=768.35 (C58H44N2=768.98) |
| 6-47 | m/z=892.38 (C68H48N2=893.12) | 6-48 | m/z=890.37 (C68H46N2=891.11) |
| 6-49 | m/z=758.28 (C55H38N2S=758.97) | 6-50 | m/z=742.30 (C55H38N2O=742.90) |
| 7-2 | m/z=586.24 (C44H30N2=586.72) | 7-4 | m/z=612.26 (C46H32N2=612.76) |
| 7-5 | m/z=642.21 (C46H30N2S=642.81) | 7-6 | m/z=626.24 (C46H30N2O=626.74) |
| 7-7 | m/z=703.30 (C52H37N3=703.87) | 7-9 | m/z=652.29 (C49H36N2=652.82) |
| 7-10 | m/z=776.32 (C59H40N2=776.96) | 7-11 | m/z=774.30 (C59H38N2=774.95) |
| 7-12 | m/z=636.26 (C48H32N2=636.78) | 7-14 | m/z=662.27 (C50H34N2=662.82) |
| 7-16 | m/z=692.23 (C50H32N2S=692.87) | 7-17 | m/z=676.25 (C50H32N2O=676.80) |
| 7-18 | m/z=753.31 (C56H39N3=753.93) | 7-19 | m/z=702.30 (C53H38N2=702.88) |
| 7-20 | m/z=826.33 (C63H42N2=827.02) | 7-21 | m/z=824.32 (C63H40N2=825.01) |
| 7-22 | m/z=688.29 (C52H36N2=688.86) | 7-25 | m/z=728.32 (C55H40N2=728.92) |
| 7-26 | m/z=852.35 (C65H44N2=853.06) | 7-27 | m/z=850.33 (C65H42N2=851.04) |
| 7-30 | m/z=718.24 (C52H34N2S=718.90) | 7-31 | m/z=702.27 (C52H34N2O=702.84) |
| 7-38 | m/z=652.29 (C49H36N2=652.82) | 7-39 | m/z=682.24 (C49H34N2S=682.87) |
| 7-40 | m/z=666.27 (C49H34N2O=666.81) | 7-41 | m/z=743.33 (C55H41N3=743.93) |
| 7-43 | m/z=692.32 (C52H40N2=692.89) | 7-44 | m/z=816.35 (C62H44N2=817.03) |
| 7-45 | m/z=814.33 (C62H42N2=815.01) | 7-46 | m/z=676.29 (C51H36N2=676.84) |
| 7-48 | m/z=702.30 (C53H38N2=702.88) | 7-50 | m/z=732.26 (C53H36N2S=732.93) |
| 7-51 | m/z=716.28 (C53H36N2O=716.87) | 7-52 | m/z=793.35 (C59H43N3=793.99) |
| 7-53 | m/z=742.33 (C56H42N2=742.95) | 7-54 | m/z=866.37 (C66H46N2=867.08) |
| 7-55 | m/z=864.35 (C66H44N2=865.07) | 7-56 | m/z=728.32 (C55H40N2=728.92) |
| 7-58 | m/z=768.35 (C58H44N2=768.98) | 7-59 | m/z=892.38 (C68H48N2=893.12) |
| 7-60 | m/z=890.37 (C68H46N2=891.11) | 7-61 | m/z=758.28 (C55H38N2S=758.97) |
| 7-62 | m/z=742.30 (C55H38N2O=742.90) | 7-63 | m/z=819.36 (C61H45N3=820.03) |
| 8-2 | m/z=636.26 (C48H32N2=636.78) | 8-4 | m/z=662.27 (C50H34N2=662.82) |
| 8-5 | m/z=692.23 (C50H32N2S=692.87) | 8-6 | m/z=676.25 (C50H32N2O=676.80) |
| 8-7 | m/z=753.31 (C56H39N3=753.93) | 8-9 | m/z=702.30 (C53H38N2=702.88) |
| 8-10 | m/z=826.33 (C63H42N2=827.02) | 8-11 | m/z=824.32 (C63H40N2=825.01) |
| 8-12 | m/z=686.27 (C52H34N2=686.84) | 8-14 | m/z=712.29 (C54H36N2=712.88) |
| 8-16 | m/z=742.24 (C54H34N2S=742.93) | 8-17 | m/z=726.27 (C54H34N2O=726.86) |
| 8-18 | m/z=803.33 (C60H41N3=803.99) | 8-19 | m/z=752.32 (C57H40N2=752.94) |
| 8-20 | m/z=876.35 (C67H44N2=877.08) | 8-21 | m/z=874.33 (C67H42N2=875.06) |
| 8-22 | m/z=738.30 (C56H38N2=738.91) | 8-23 | m/z=788.32 (C60H40N2=788.97) |
| 8-25 | m/z=778.33 (C59H42N2=778.98) | 8-26 | m/z=902.37 (C69H46N2=903.12) |
| 8-27 | m/z=900.35 (C69H44N2=901.10) | 8-30 | m/z=768.26 (C56H36N2S=768.96) |
| 8-31 | m/z=752.28 (C56H36N2O=752.90) | 8-32 | m/z=829.35 (C62H43N3=830.02) |
| 8-34 | m/z=626.27 (C47H34N2=626.79) | 8-35 | m/z=676.29 (C51H36N2=676.84) |
| 8-36 | m/z=676.29 (C51H36N2=676.84) | 8-37 | m/z=702.30 (C53H38N2=702.88) |
| 8-38 | m/z=732.26 (C53H36N2S=732.93) | 8-39 | m/z=716.28 (C53H36N2O=716.87) |
| 8-40 | m/z=793.35 (C59H43N3=793.99) | 8-42 | m/z=742.33 (C56H42N2=742.95) |
| 8-43 | m/z=866.37 (C66H46N2=867.08) | 8-44 | m/z=864.35 (C66H44N2=865.07) |
| 8-45 | m/z=726.30 (C55H38N2=726.90) | 8-47 | m/z=752.32 (C57H40N2=752.94) |
| 8-49 | m/z=782.28 (C57H38N2S=782.99) | 8-50 | m/z=766.30 (C57H38N2O=766.92) |
| 8-51 | m/z=843.36 (C63H45N3=844.05) | 8-52 | m/z=792.35 (C60H44N2=793.00) |
| 8-53 | m/z=916.38 (C70H48N2=917.14) | 8-54 | m/z=914.37 (C70H46N2=915.13) |
| 8-55 | m/z=778.33 (C59H42N2=778.98) | 8-57 | m/z=818.37 (C62H46N2=819.04) |
| 8-58 | m/z=942.40 (C72H50N2=943.18) | 8-59 | m/z=940.38 (C72H48N2=941.16) |
| 8-60 | m/z=808.29 (C59H40N2S=809.03) | 8-61 | m/z=792.31 (C59H40N2O=792.96) |
| 8-62 | m/z=869.38 (C65H47N3=870.09) | 9-1 | m/z=538.24 (C40H30N2=538.68) |
| 9-2 | m/z=588.26 (C44H32N2=588.74) | 9-3 | m/z=588.26 (C44H32N2=588.74) |
| 9-4 | m/z=614.27 (C46H34N2=614.78) | 9-5 | m/z=644.23 (C46H32N2S=644.82) |
| 9-6 | m/z=628.25 (C46H32N2O=628.76) | 9-7 | m/z=654.30 (C49H38N2=654.84) |
| 9-8 | m/z=778.33 (C59H42N2=778.98) | 9-9 | m/z=776.32 (C59H40N2=776.96) |
| 9-10 | m/z=664.29 (C50H36N2=664.83) | 9-11 | m/z=704.32 (C53H40N2=704.90) |
| 9-12 | m/z=828.35 (C63H44N2=829.04) | 9-13 | m/z=826.33 (C63H42N2=827.02) |
| 9-14 | m/z=694.24 (C50H34N2S=694.88) | 9-15 | m/z=678.27 (C50H34N2O=678.82) |
| 9-16 | m/z=664.29 (C50H36N2=664.83) | 9-17 | m/z=690.30 (C52H38N2=690.87) |
| 9-18 | m/z=730.33 (C55H42N2=730.94) | 9-19 | m/z=854.37 (C65H46N2=855.07) |
| 9-20 | m/z=852.35 (C65H44N2=853.06) | 9-21 | m/z=720.26 (C52H36N2S=720.92) |
| 9-22 | m/z=704.28 (C52H36N2O=704.86) | 9-23 | m/z=640.29 (C48H36N2=640.81) |
| 9-24 | m/z=680.32 (C51H40N2=680.88) | 9-25 | m/z=804.35 (C61H44N2=805.02) |
| 9-26 | m/z=802.33 (C61H42N2=803.00) | 9-27 | m/z=746.28 (C54H38N2S=746.96) |
| 9-28 | m/z=730.30 (C54H38N2O=730.89) | 9-29 | m/z=796.29 (C58H40N2S=797.02) |
| 9-30 | m/z=780.31 (C58H40N2O=780.95) | 9-31 | m/z=918.37 (C68H46N4=919.12) |
| 9-32 | m/z=970.40 (C72H50N4=971.19) | 9-33 | m/z=578.27 (C43H34N2=578.74) |
| 9-34 | m/z=628.29 (C47H36N2=628.80) | 9-35 | m/z=628.29 (C47H36N2=628.80) |
| 9-36 | m/z=654.30 (C49H38N2=654.84) | 9-37 | m/z=684.26 (C49H36N2S=684.89) |
| 9-38 | m/z=668.28 (C49H36N2O=668.82) | 9-39 | m/z=694.33 (C52H42N2=694.90) |
| 9-40 | m/z=818.37 (C62H46N2=819.04) | 9-41 | m/z=816.35 (C62H44N2=817.03) |
| 9-42 | m/z=704.32 (C53H40N2=704.90) | 9-43 | m/z=744.35 (C56H44N2=744.96) |
| 9-44 | m/z=868.38 (C66H48N2=869.10) | 9-45 | m/z=866.37(C66H46N2=867.08) |
| 9-46 | m/z=734.28 (C53H38N2S=734.95) | 9-47 | m/z=718.30 (C53H38N2O=718.88) |
| 9-48 | m/z=704.32 (C53H40N2=704.90) | 9-49 | m/z=730.33 (C55H42N2=730.94) |
| 9-50 | m/z=770.37 (C58H46N2=771.00) | 9-51 | m/z=894.40 (C68H50N2=895.14) |
| 9-52 | m/z=892.38 (C68H48N2=893.12) | 9-53 | m/z=760.29 (C55H40N2S=760.98) |
| 9-54 | m/z=744.31 (C55H40N2O=744.92) | 9-55 | m/z=680.32 (C51H40N2=680.88) |
| 9-56 | m/z=720.35 (C54H44N2=720.94) | 9-57 | m/z=844.38 (C64H48N2=845.08) |
| 9-58 | m/z=842.37 (C64H46N2=843.06) | 9-59 | m/z=786.31 (C57H42N2S=787.02) |
| 9-60 | m/z=770.33 (C57H42N2O=770.96) | 9-61 | m/z=836.32 (C61H44N2S=837.08) |
| 9-62 | m/z=820.35 (C61H44N2O=821.01) | 9-63 | m/z=958.40 (C71H50N4=959.18) |
| 10-2 | m/z=636.26 (C48H32N2=636.78) | 10-4 | m/z=662.27 (C50H34N2=662.82) |
| 10-6 | m/z=692.23 (C50H32N2S=692.87) | 10-7 | m/z=676.25 (C50H32N2O=676.80) |
| 10-10 | m/z=702.30 (C53H38N2=702.88) | 10-11 | m/z=826.33 (C63H42N2=827.02) |
| 10-12 | m/z=824.32 (C63H40N2=825.01) | 10-13 | m/z=712.29 (C54H36N2=712.88) |
| 10-14 | m/z=742.24 (C54H34N2S=742.93) | 10-15 | m/z=726.27 (C54H34N2O=726.86) |
| 10-16 | m/z=752.32 (C57H40N2=752.94) | 10-17 | m/z=876.35 (C67H44N2=877.08) |
| 10-18 | m/z=874.33 (C67H42N2=875.06) | 10-19 | m/z=738.30 (C56H38N2=738.91) |
| 10-20 | m/z=778.33 (C59H42N2=778.98) | 10-21 | m/z=902.37 (C69H46N2=903.12) |
| 10-22 | m/z=900.35 (C69H44N2=901.10) | 10-23 | m/z=768.26 (C56H36N2S=768.96) |
| 10-24 | m/z=752.28 (C56H36N2O=752.90) | 10-27 | m/z=626.27 (C47H34N2=626.79) |
| 10-28 | m/z=676.29 (C51H36N2=676.84) | 10-30 | m/z=702.30 (C53H38N2=702.88) |
| 10-31 | m/z=702.30 (C53H38N2=702.88) | 10-32 | m/z=732.26 (C53H36N2S=732.93) |
| 10-33 | m/z=716.28 (C53H36N2O=716.87) | 10-34 | m/z=793.3 (C59H43N3=793.99) |
| 10-36 | m/z=742.33 (C56H42N2=742.95) | 10-37 | m/z=866.37 (C66H46N2=867.08) |
| 10-38 | m/z=864.35 (C66H44N2=865.07) | 10-39 | m/z=752.32 (C57H40N2=752.94) |
| 10-40 | m/z=782.28 (C57H38N2S=782.99) | 10-41 | m/z=766.30 (C57H38N2O=766.92) |
| 10-45 | m/z=778.33 (C59H42N2=778.98) | 10-49 | m/z=808.29 (C59H40N2S=809.03) |
| 10-50 | m/z=792.31 (C59H40N2O=792.96) |
| compound | FD-MS | compound | FD-MS |
| 3-26 | m / z = 638.27 (C 48 H 34 N 2 = 638.80) | 3-29 | m / z = 678.30 (C 51 H 38 N 2 = 678.86) |
| 3-30 | m / z = 802.33 (C 61 H 42 N 2 = 803.00) | 3-31 | m / z = 800.32 (C 61 H 40 N 2 = 800.98) |
| 3-34 | m / z = 668.23 (C 48 H 32 N 2 S = 668.85) | 3-35 | m / z = 652.25 (C 48 H 32 N 2 O = 652.78) |
| 3-36 | m / z = 729.31 (C 54 H 39 N 3 = 729.91) | 3-66 | m / z = 678.30 (C 51 H 38 N 2 = 678.86) |
| 3-68 | m / z = 718.33 (C 54 H 42 N 2 = 718.92) | 3-69 | m / z = 842.37 (C 64 H 46 N 2 = 843.06) |
| 3-70 | m / z = 840.35 (C 64 H 44 N 2 = 841.05) | 3-71 | m / z = 708.26 (C 51 H 36 N 2 S = 708.91) |
| 3-72 | m / z = 692.28 (C 51 H 36 N 2 O = 692.84) | 3-73 | m / z = 769.35 (C 57 H 43 N 3 = 769.97) |
| 4-4 | m / z = 638.27 (C 48 H 34 N 2 = 638.80) | 4-7 | m / z = 652.25 (C 48 H 32 N 2 O = 652.78) |
| 4-8 | m / z = 668.23 (C 48 H 32 N 2 S = 668.85) | 4-9 | m / z = 678.30 (C 51 H 38 N 2 = 678.86) |
| 4-10 | m / z = 802.33 (C 61 H 42 N 2 = 803.00) | 4-11 | m / z = 800.32 (C 61 H 40 N 2 = 800.98) |
| 4-27 | m / z = 714.30 (C 54 H 38 N 2 = 714.89) | 4-30 | m / z = 728.28 (C 54 H 36 N 2 O = 728.88) |
| 4-31 | m / z = 744.26 (C 54 H 36 N 2 S = 744.94) | 4-32 | m / z = 754.33 (C 57 H 42 N 2 = 754.96) |
| 4-33 | m / z = 878.37 (C 67 H 46 N 2 = 879.10) | 4-34 | m / z = 876.35 (C 67 H 44 N 2 = 877.08) |
| 4-35 | m / z = 678.30 (C 51 H 38 N 2 = 678.86) | 4-43 | m / z = 714.30 (C 54 H 38 N 2 = 714.89) |
| 4-44 | m / z = 754.33 (C 57 H 42 N 2 = 754.96) | 4-45 | m / z = 878.37 (C 67 H 46 N 2 = 879.10) |
| 4-46 | m / z = 876.35 (C 67 H 44 N 2 = 877.08) | 4-47 | m / z = 744.26 (C 54 H 36 N 2 S = 744.94) |
| 4-49 | m / z = 678.30 (C 51 H 38 N 2 = 678.86) | 4-50 | m / z = 802.33 (C 61 H 42 N 2 = 803.00) |
| 4-51 | m / z = 800.32 (C 61 H 40 N 2 = 800.98) | 4-55 | m / z = 638.27 (C 48 H 34 N 2 = 638.80) |
| 4-56 | m / z = 688.29 (C 52 H 36 N 2 = 688.86) | 4-58 | m / z = 714.30 (C 54 H 38 N 2 = 714.89) |
| 4-61 | m / z = 728.28 (C 54 H 36 N 2 O = 728.88) | 4-62 | m / z = 744.26 (C 54 H 36 N 2 S = 744.94) |
| 4-63 | m / z = 754.33 (C 57 H 42 N 2 = 754.96) | 4-64 | m / z = 878.37 (C 67 H 46 N 2 = 879.10) |
| 4-65 | m / z = 876.35 (C 67 H 44 N 2 = 877.08) | 4-66 | m / z = 678.30 (C 51 H 38 N 2 = 678.86) |
| 4-67 | m / z = 802.33 (C 61 H 42 N 2 = 803.00) | 4-68 | m / z = 800.32 (C 61 H 40 N 2 = 800.98) |
| 4-103 | m / z = 754.33 (C 57 H 42 N 2 = 754.96) | 4-104 | m / z = 878.37 (C 67 H 46 N 2 = 879.10) |
| 4-105 | m / z = 876.35 (C 67 H 44 N 2 = 877.08) | 4-106 | m / z = 804.35 (C 61 H 44 N 2 = 805.02) |
| 4-107 | m / z = 928.38 (C 71 H 48 N 2 = 929.15) | 4-108 | m / z = 926.37 (C 71 H 46 N 2 = 927.14) |
| 5-2 | m / z = 586.24 (C 44 H 30 N 2 = 586.72) | 5-4 | m / z = 612.26 (C 46 H 32 N 2 = 612.76) |
| 5-6 | m / z = 642.21 (C 46 H 30 N 2 S = 642.81) | 5-7 | m / z = 626.24 (C 46 H 32 N 2 O = 626.74) |
| 5-8 | m / z = 703.30 (C 52 H 37 N 3 = 703.87) | 5-10 | m / z = 652.29 (C 49 H 36 N 2 = 652.82) |
| 5-11 | m / z = 776.32 (C 59 H 40 N 2 = 776.96) | 5-12 | m / z = 774.30 (C 59 H 38 N 2 = 774.95) |
| 5-13 | m / z = 662.27 (C 50 H 34 N 2 = 662.82) | 5-16 | m / z = 702.30 (C 53 H 38 N 2 = 702.88) |
| 5-17 | m / z = 826.33 (C 63 H 42 N 2 = 827.02) | 5-18 | m / z = 824.32 (C 63 H 40 N 2 = 825.01) |
| 5-19 | m / z = 688.29 (C 52 H 36 N 2 = 688.86) | 5-20 | m / z = 728.32 (C 55 H 40 N 2 = 728.92) |
| 5-21 | m / z = 852.35 (C 65 H 44 N 2 = 853.06) | 5-22 | m / z = 850.33 (C 65 H 42 N 2 = 851.04) |
| 5-23 | m / z = 718.24 (C 52 H 34 N 2 S = 718.90) | 5-24 | m / z = 702.27 (C 52 H 34 N 2 O = 702.84) |
| 5-36 | m / z = 692.32 (C 52 H 40 N 2 = 692.89) | 5-37 | m / z = 816.35 (C 62 H 44 N 2 = 817.03) |
| 5-38 | m / z = 814.33 (C 62 H 42 N 2 = 815.01) | 5-39 | m / z = 702.30 (C 53 H 38 N 2 = 702.88) |
| 5-42 | m / z = 742.33 (C 56 H 42 N 2 = 742.95) | 5-43 | m / z = 866.37 (C 66 H 46 N 2 = 867.08) |
| 5-44 | m / z = 864.35 (C 66 H 44 N 2 = 865.07) | 5-45 | m / z = 728.32 (C 55 H 40 N 2 = 728.92) |
| 5-46 | m / z = 768.35 (C 58 H 44 N 2 = 768.98) | 5-47 | m / z = 892.38 (C 68 H 48 N 2 = 893.12) |
| 5-48 | m / z = 890.37 (C 68 H 46 N 2 = 891.11) | 5-49 | m / z = 758.28 (C 55 H 38 N 2 S = 758.97) |
| 5-50 | m / z = 742.30 (C 55 H 38 N 2 O = 742.90) | 6-2 | m / z = 586.24 (C 44 H 30 N 2 = 586.72) |
| 6-4 | m / z = 612.26 (C 46 H 32 N 2 = 612.76) | 6-6 | m / z = 642.21 (C 46 H 30 N 2 S = 642.81) |
| 6-7 | m / z = 626.24 (C 46 H 30 N 2 O = 626.74) | 6-8 | m / z = 703.30 (C 52 H 37 N 3 = 703.87) |
| 6-10 | m / z = 652.29 (C 49 H 36 N 2 = 652.82) | 6-11 | m / z = 776.32 (C 59 H 40 N 2 = 776.96) |
| 6-12 | m / z = 774.30 (C 59 H 38 N 2 = 774.95) | 6-13 | m / z = 662.27 (C 50 H 34 N 2 = 662.82) |
| 6-16 | m / z = 702.30 (C 53 H 38 N 2 = 702.88) | 6-17 | m / z = 826.33 (C 63 H 42 N 2 = 827.02) |
| 6-18 | m / z = 824.32 (C 63 H 40 N 2 = 825.01) | 6-19 | m / z = 688.29 (C 52 H 36 N 2 = 688.86) |
| 6-20 | m / z = 728.32 (C 55 H 40 N 2 = 728.92) | 6-21 | m / z = 852.35 (C 65 H 44 N 2 = 853.06) |
| 6-22 | m / z = 850.33 (C 65 H 42 N 2 = 851.04) | 6-23 | m / z = 718.24 (C 52 H 34 N 2 S = 718.90) |
| 6-24 | m / z = 702.27 (C 52 H 34 N 2 O = 702.84) | 6-36 | m / z = 692.32 (C 52 H 40 N 2 = 692.89) |
| 6-37 | m / z = 816.35 (C 62 H 44 N 2 = 817.03) | 6-38 | m / z = 814.33 (C 62 H 42 N 2 = 815.01) |
| 6-39 | m / z = 702.30 (C 53 H 38 N 2 = 702.88) | 6-40 | m / z = 732.26 (C 53 H 36 N 2 S = 732.93) |
| 6-41 | m / z = 716.28 (C 53 H 36 N 2 O = 716.87) | 6-42 | m / z = 742.33 (C 56 H 42 N 2 = 742.95) |
| 6-43 | m / z = 866.37 (C 66 H 46 N 2 = 867.08) | 6-44 | m / z = 864.35 (C 66 H 44 N 2 = 865.07) |
| 6-45 | m / z = 728.32 (C 55 H 40 N 2 = 728.92) | 6-46 | m / z = 768.35 (C 58 H 44 N 2 = 768.98) |
| 6-47 | m / z = 892.38 (C 68 H 48 N 2 = 893.12) | 6-48 | m / z = 890.37 (C 68 H 46 N 2 = 891.11) |
| 6-49 | m / z = 758.28 (C 55 H 38 N 2 S = 758.97) | 6-50 | m / z = 742.30 (C 55 H 38 N 2 O = 742.90) |
| 7-2 | m / z = 586.24 (C 44 H 30 N 2 = 586.72) | 7-4 | m / z = 612.26 (C 46 H 32 N 2 = 612.76) |
| 7-5 | m / z = 642.21 (C 46 H 30 N 2 S = 642.81) | 7-6 | m / z = 626.24 (C 46 H 30 N 2 O = 626.74) |
| 7-7 | m / z = 703.30 (C 52 H 37 N 3 = 703.87) | 7-9 | m / z = 652.29 (C 49 H 36 N 2 = 652.82) |
| 7-10 | m / z = 776.32 (C 59 H 40 N 2 = 776.96) | 7-11 | m / z = 774.30 (C 59 H 38 N 2 = 774.95) |
| 7-12 | m / z = 636.26 (C 48 H 32 N 2 = 636.78) | 7-14 | m / z = 662.27 (C 50 H 34 N 2 = 662.82) |
| 7-16 | m / z = 692.23 (C 50 H 32 N 2 S = 692.87) | 7-17 | m / z = 676.25 (C 50 H 32 N 2 O = 676.80) |
| 7-18 | m / z = 753.31 (C 56 H 39 N 3 = 753.93) | 7-19 | m / z = 702.30 (C 53 H 38 N 2 = 702.88) |
| 7-20 | m / z = 826.33 (C 63 H 42 N 2 = 827.02) | 7-21 | m / z = 824.32 (C 63 H 40 N 2 = 825.01) |
| 7-22 | m / z = 688.29 (C 52 H 36 N 2 = 688.86) | 7-25 | m / z = 728.32 (C 55 H 40 N 2 = 728.92) |
| 7-26 | m / z = 852.35 (C 65 H 44 N 2 = 853.06) | 7-27 | m / z = 850.33 (C 65 H 42 N 2 = 851.04) |
| 7-30 | m / z = 718.24 (C 52 H 34 N 2 S = 718.90) | 7-31 | m / z = 702.27 (C 52 H 34 N 2 O = 702.84) |
| 7-38 | m / z = 652.29 (C 49 H 36 N 2 = 652.82) | 7-39 | m / z = 682.24 (C 49 H 34 N 2 S = 682.87) |
| 7-40 | m / z = 666.27 (C 49 H 34 N 2 O = 666.81) | 7-41 | m / z = 743.33 (C 55 H 41 N 3 = 743.93) |
| 7-43 | m / z = 692.32 (C 52 H 40 N 2 = 692.89) | 7-44 | m / z = 816.35 (C 62 H 44 N 2 = 817.03) |
| 7-45 | m / z = 814.33 (C 62 H 42 N 2 = 815.01) | 7-46 | m / z = 676.29 (C 51 H 36 N 2 = 676.84) |
| 7-48 | m / z = 702.30 (C 53 H 38 N 2 = 702.88) | 7-50 | m / z = 732.26 (C 53 H 36 N 2 S = 732.93) |
| 7-51 | m / z = 716.28 (C 53 H 36 N 2 O = 716.87) | 7-52 | m / z = 793.35 (C 59 H 43 N 3 = 793.99) |
| 7-53 | m / z = 742.33 (C 56 H 42 N 2 = 742.95) | 7-54 | m / z = 866.37 (C 66 H 46 N 2 = 867.08) |
| 7-55 | m / z = 864.35 (C 66 H 44 N 2 = 865.07) | 7-56 | m / z = 728.32 (C 55 H 40 N 2 = 728.92) |
| 7-58 | m / z = 768.35 (C 58 H 44 N 2 = 768.98) | 7-59 | m / z = 892.38 (C 68 H 48 N 2 = 893.12) |
| 7-60 | m / z = 890.37 (C 68 H 46 N 2 = 891.11) | 7-61 | m / z = 758.28 (C 55 H 38 N 2 S = 758.97) |
| 7-62 | m / z = 742.30 (C 55 H 38 N 2 O = 742.90) | 7-63 | m / z = 819.36 (C 61 H 45 N 3 = 820.03) |
| 8-2 | m / z = 636.26 (C 48 H 32 N 2 = 636.78) | 8-4 | m / z = 662.27 (C 50 H 34 N 2 = 662.82) |
| 8-5 | m / z = 692.23 (C 50 H 32 N 2 S = 692.87) | 8-6 | m / z = 676.25 (C 50 H 32 N 2 O = 676.80) |
| 8-7 | m / z = 753.31 (C 56 H 39 N 3 = 753.93) | 8-9 | m / z = 702.30 (C 53 H 38 N 2 = 702.88) |
| 8-10 | m / z = 826.33 (C 63 H 42 N 2 = 827.02) | 8-11 | m / z = 824.32 (C 63 H 40 N 2 = 825.01) |
| 8-12 | m / z = 686.27 (C 52 H 34 N 2 = 686.84) | 8-14 | m / z = 712.29 (C 54 H 36 N 2 = 712.88) |
| 8-16 | m / z = 742.24 (C 54 H 34 N 2 S = 742.93) | 8-17 | m / z = 726.27 (C 54 H 34 N 2 O = 726.86) |
| 8-18 | m / z = 803.33 (C 60 H 41 N 3 = 803.99) | 8-19 | m / z = 752.32 (C 57 H 40 N 2 = 752.94) |
| 8-20 | m / z = 876.35 (C 67 H 44 N 2 = 877.08) | 8-21 | m / z = 874.33 (C 67 H 42 N 2 = 875.06) |
| 8-22 | m / z = 738.30 (C 56 H 38 N 2 = 738.91) | 8-23 | m / z = 788.32 (C 60 H 40 N 2 = 788.97) |
| 8-25 | m / z = 778.33 (C 59 H 42 N 2 = 778.98) | 8-26 | m / z = 902.37 (C 69 H 46 N 2 = 903.12) |
| 8-27 | m / z = 900.35 (C 69 H 44 N 2 = 901.10) | 8-30 | m / z = 768.26 (C 56 H 36 N 2 S = 768.96) |
| 8-31 | m / z = 752.28 (C 56 H 36 N 2 O = 752.90) | 8-32 | m / z = 829.35 (C 62 H 43 N 3 = 830.02) |
| 8-34 | m / z = 626.27 (C 47 H 34 N 2 = 626.79) | 8-35 | m / z = 676.29 (C 51 H 36 N 2 = 676.84) |
| 8-36 | m / z = 676.29 (C 51 H 36 N 2 = 676.84) | 8-37 | m / z = 702.30 (C 53 H 38 N 2 = 702.88) |
| 8-38 | m / z = 732.26 (C 53 H 36 N 2 S = 732.93) | 8-39 | m / z = 716.28 (C 53 H 36 N 2 O = 716.87) |
| 8-40 | m / z = 793.35 (C 59 H 43 N 3 = 793.99) | 8-42 | m / z = 742.33 (C 56 H 42 N 2 = 742.95) |
| 8-43 | m / z = 866.37 (C 66 H 46 N 2 = 867.08) | 8-44 | m / z = 864.35 (C 66 H 44 N 2 = 865.07) |
| 8-45 | m / z = 726.30 (C 55 H 38 N 2 = 726.90) | 8-47 | m / z = 752.32 (C 57 H 40 N 2 = 752.94) |
| 8-49 | m / z = 782.28 (C 57 H 38 N 2 S = 782.99) | 8-50 | m / z = 766.30 (C 57 H 38 N 2 O = 766.92) |
| 8-51 | m / z = 843.36 (C 63 H 45 N 3 = 844.05) | 8-52 | m / z = 792.35 (C 60 H 44 N 2 = 793.00) |
| 8-53 | m / z = 916.38 (C 70 H 48 N 2 = 917.14) | 8-54 | m / z = 914.37 (C 70 H 46 N 2 = 915.13) |
| 8-55 | m / z = 778.33 (C 59 H 42 N 2 = 778.98) | 8-57 | m / z = 818.37 (C 62 H 46 N 2 = 819.04) |
| 8-58 | m / z = 942.40 (C 72 H 50 N 2 = 943.18) | 8-59 | m / z = 940.38 (C 72 H 48 N 2 = 941.16) |
| 8-60 | m / z = 808.29 (C 59 H 40 N 2 S = 809.03) | 8-61 | m / z = 792.31 (C 59 H 40 N 2 O = 792.96) |
| 8-62 | m / z = 869.38 (C 65 H 47 N 3 = 870.09) | 9-1 | m / z = 538.24 (C 40 H 30 N 2 = 538.68) |
| 9-2 | m / z = 588.26 (C 44 H 32 N 2 = 588.74) | 9-3 | m / z = 588.26 (C 44 H 32 N 2 = 588.74) |
| 9-4 | m / z = 614.27 (C 46 H 34 N 2 = 614.78) | 9-5 | m / z = 644.23 (C 46 H 32 N 2 S = 644.82) |
| 9-6 | m / z = 628.25 (C 46 H 32 N 2 O = 628.76) | 9-7 | m / z = 654.30 (C 49 H 38 N 2 = 654.84) |
| 9-8 | m / z = 778.33 (C 59 H 42 N 2 = 778.98) | 9-9 | m / z = 776.32 (C 59 H 40 N 2 = 776.96) |
| 9-10 | m / z = 664.29 (C 50 H 36 N 2 = 664.83) | 9-11 | m / z = 704.32 (C 53 H 40 N 2 = 704.90) |
| 9-12 | m / z = 828.35 (C 63 H 44 N 2 = 829.04) | 9-13 | m / z = 826.33 (C 63 H 42 N 2 = 827.02) |
| 9-14 | m / z = 694.24 (C 50 H 34 N 2 S = 694.88) | 9-15 | m / z = 678.27 (C 50 H 34 N 2 O = 678.82) |
| 9-16 | m / z = 664.29 (C 50 H 36 N 2 = 664.83) | 9-17 | m / z = 690.30 (C 52 H 38 N 2 = 690.87) |
| 9-18 | m / z = 730.33 (C 55 H 42 N 2 = 730.94) | 9-19 | m / z = 854.37 (C 65 H 46 N 2 = 855.07) |
| 9-20 | m / z = 852.35 (C 65 H 44 N 2 = 853.06) | 9-21 | m / z = 720.26 (C 52 H 36 N 2 S = 720.92) |
| 9-22 | m / z = 704.28 (C 52 H 36 N 2 O = 704.86) | 9-23 | m / z = 640.29 (C 48 H 36 N 2 = 640.81) |
| 9-24 | m / z = 680.32 (C 51 H 40 N 2 = 680.88) | 9-25 | m / z = 804.35 (C 61 H 44 N 2 = 805.02) |
| 9-26 | m / z = 802.33 (C 61 H 42 N 2 = 803.00) | 9-27 | m / z = 746.28 (C 54 H 38 N 2 S = 746.96) |
| 9-28 | m / z = 730.30 (C 54 H 38 N 2 O = 730.89) | 9-29 | m / z = 796.29 (C 58 H 40 N 2 S = 797.02) |
| 9-30 | m / z = 780.31 (C 58 H 40 N 2 O = 780.95) | 9-31 | m / z = 918.37 (C 68 H 46 N 4 = 919.12) |
| 9-32 | m / z = 970.40 (C 72 H 50 N 4 = 971.19) | 9-33 | m / z = 578.27 (C 43 H 34 N 2 = 578.74) |
| 9-34 | m / z = 628.29 (C 47 H 36 N 2 = 628.80) | 9-35 | m / z = 628.29 (C 47 H 36 N 2 = 628.80) |
| 9-36 | m / z = 654.30 (C 49 H 38 N 2 = 654.84) | 9-37 | m / z = 684.26 (C 49 H 36 N 2 S = 684.89) |
| 9-38 | m / z = 668.28 (C 49 H 36 N 2 O = 668.82) | 9-39 | m / z = 694.33 (C 52 H 42 N 2 = 694.90) |
| 9-40 | m / z = 818.37 (C 62 H 46 N 2 = 819.04) | 9-41 | m / z = 816.35 (C 62 H 44 N 2 = 817.03) |
| 9-42 | m / z = 704.32 (C 53 H 40 N 2 = 704.90) | 9-43 | m / z = 744.35 (C 56 H 44 N 2 = 744.96) |
| 9-44 | m / z = 868.38 (C 66 H 48 N 2 = 869.10) | 9-45 | m / z = 866.37 (C 66 H 46 N 2 = 867.08) |
| 9-46 | m / z = 734.28 (C 53 H 38 N 2 S = 734.95) | 9-47 | m / z = 718.30 (C 53 H 38 N 2 O = 718.88) |
| 9-48 | m / z = 704.32 (C 53 H 40 N 2 = 704.90) | 9-49 | m / z = 730.33 (C 55 H 42 N 2 = 730.94) |
| 9-50 | m / z = 770.37 (C 58 H 46 N 2 = 771.00) | 9-51 | m / z = 894.40 (C 68 H 50 N 2 = 895.14) |
| 9-52 | m / z = 892.38 (C 68 H 48 N 2 = 893.12) | 9-53 | m / z = 760.29 (C 55 H 40 N 2 S = 760.98) |
| 9-54 | m / z = 744.31 (C 55 H 40 N 2 O = 744.92) | 9-55 | m / z = 680.32 (C 51 H 40 N 2 = 680.88) |
| 9-56 | m / z = 720.35 (C 54 H 44 N 2 = 720.94) | 9-57 | m / z = 844.38 (C 64 H 48 N 2 = 845.08) |
| 9-58 | m / z = 842.37 (C 64 H 46 N 2 = 843.06) | 9-59 | m / z = 786.31 (C 57 H 42 N 2 S = 787.02) |
| 9-60 | m / z = 770.33 (C 57 H 42 N 2 O = 770.96) | 9-61 | m / z = 836.32 (C 61 H 44 N 2 S = 837.08) |
| 9-62 | m / z = 820.35 (C 61 H 44 N 2 O = 821.01) | 9-63 | m / z = 958.40 (C 71 H 50 N 4 = 959.18) |
| 10-2 | m / z = 636.26 (C 48 H 32 N 2 = 636.78) | 10-4 | m / z = 662.27 (C 50 H 34 N 2 = 662.82) |
| 10-6 | m / z = 692.23 (C 50 H 32 N 2 S = 692.87) | 10-7 | m / z = 676.25 (C 50 H 32 N 2 O = 676.80) |
| 10-10 | m / z = 702.30 (C 53 H 38 N 2 = 702.88) | 10-11 | m / z = 826.33 (C 63 H 42 N 2 = 827.02) |
| 10-12 | m / z = 824.32 (C 63 H 40 N 2 = 825.01) | 10-13 | m / z = 712.29 (C 54 H 36 N 2 = 712.88) |
| 10-14 | m / z = 742.24 (C 54 H 34 N 2 S = 742.93) | 10-15 | m / z = 726.27 (C 54 H 34 N 2 O = 726.86) |
| 10-16 | m / z = 752.32 (C 57 H 40 N 2 = 752.94) | 10-17 | m / z = 876.35 (C 67 H 44 N 2 = 877.08) |
| 10-18 | m / z = 874.33 (C 67 H 42 N 2 = 875.06) | 10-19 | m / z = 738.30 (C 56 H 38 N 2 = 738.91) |
| 10-20 | m / z = 778.33 (C 59 H 42 N 2 = 778.98) | 10-21 | m / z = 902.37 (C 69 H 46 N 2 = 903.12) |
| 10-22 | m / z = 900.35 (C 69 H 44 N 2 = 901.10) | 10-23 | m / z = 768.26 (C 56 H 36 N 2 S = 768.96) |
| 10-24 | m / z = 752.28 (C 56 H 36 N 2 O = 752.90) | 10-27 | m / z = 626.27 (C 47 H 34 N 2 = 626.79) |
| 10-28 | m / z = 676.29 (C 51 H 36 N 2 = 676.84) | 10-30 | m / z = 702.30 (C 53 H 38 N 2 = 702.88) |
| 10-31 | m / z = 702.30 (C 53 H 38 N 2 = 702.88) | 10-32 | m / z = 732.26 (C 53 H 36 N 2 S = 732.93) |
| 10-33 | m / z = 716.28 (C 53 H 36 N 2 O = 716.87) | 10-34 | m / z = 793.3 (C 59 H 43 N 3 = 793.99) |
| 10-36 | m / z = 742.33 (C 56 H 42 N 2 = 742.95) | 10-37 | m / z = 866.37 (C 66 H 46 N 2 = 867.08) |
| 10-38 | m / z = 864.35 (C 66 H 44 N 2 = 865.07) | 10-39 | m / z = 752.32 (C 57 H 40 N 2 = 752.94) |
| 10-40 | m / z = 782.28 (C 57 H 38 N 2 S = 782.99) | 10-41 | m / z = 766.30 (C 57 H 38 N 2 O = 766.92) |
| 10-45 | m / z = 778.33 (C 59 H 42 N 2 = 778.98) | 10-49 | m / z = 808.29 (C 59 H 40 N 2 S = 809.03) |
| 10-50 | m / z = 792.31 (C 59 H 40 N 2 O = 792.96) |
한편, 상기에서는 화학식 1 또는 화학식 2로 표시되는 본 발명의 예시적 합성예를 설명하였지만, 이들은 모두 Ullmann 반응 및 Buchwald-Hartwig cross coupling 반응 등에 기초한 것으로 구체적 합성예에 명시된 치환기 이외에 다른 치환기(R1, R2, L, Ar1, Ar2 등의 치환기)가 결합되더라도 상기 반응이 진행된다는 것을 당업자라면 쉽게 이해할 수 있을 것이다. 예컨대, Sub 1, Sub 3반응은 Ullmann 반응에 기초한 것이고, Sub 2, Sub 5, Product 합성 반응식은 Buchwald-Hartwig cross coupling 반응에 기초한 것으로, 이들에 구체적으로 명시되지 않은 치환기가 결합되더라도 상기 반응들이 진행할 것이다.On the other hand, in the above described an exemplary synthesis example of the present invention represented by the formula (1) or (2), these are all based on the Ullmann reaction and Buchwald-Hartwig cross coupling reaction and the like other substituents in addition to the substituents specified in the specific synthesis example (R 1 , Those skilled in the art will readily understand that the reaction proceeds even when R 2 , L, substituents such as Ar 1 , Ar 2, etc. are combined. For example, the Sub 1 and Sub 3 reactions are based on the Ullmann reaction, and the Sub 2, Sub 5, Product synthesis scheme is based on the Buchwald-Hartw i g cross coupling reaction, even though the substituents are not specifically specified. Will proceed.
유기전기소자의 제조평가Manufacturing Evaluation of Organic Electrical Device
[실시예 6] Example 6
정공 Hole
수송층Transport layer
먼저, 유기 기판에 형성된 ITO층(양극)위에 우선 정공주입층으로서 N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (2-TNATA로 약기함) 막을 진공증착하여 60nm 두께로 형성하였고 이어서 본 발명에 따른 화합물, 비교 화합물 1을 정공 수송층으로 20nm 두께로 진공 증착 하였다. 정공수송층 위에 발광층 호스트로서는 CBP[4,4'-N,N'-dicarbazole-biphenyl], 도판트로서는 Ir(ppy)3 [tris(2-phenylpyridine)-iridium] 을 90:10 중량으로 도핑함으로써 상기 정공 수송층 위에 30nm 두께의 발광층을 증착하였다. 이어서 홀 저지층으로 (1,1’-비스페닐)-4-올레이토)비스(2-메틸-8-퀴놀린올레이토)알루미늄(이하 BAlq로 약기함)을 10 nm 두께로 진공증착하고, 전자수송층으로 트리스(8-퀴놀리놀)알루미늄(이하 Alq3로 약칭함)을 40 nm 두께로 성막하였다. 이후, 전자주입층으로 할로젠화 알칼리 금속인 LiF를 0.2 nm 두께로 증착하고, 이어서 Al을 150 nm의 두께로 증착하여 음극으로 사용함으로서 유기전계 발광소자를 제조하였다. First, N 1- (naphthalen-2-yl) -N 4 , N 4 -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl as a hole injection layer on the ITO layer (anode) formed on the organic substrate. ) -N 1 -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum deposited to form a thickness of 60 nm, and then the compound according to the present invention, Comparative Compound 1, was vacuum deposited to a hole transport layer at a thickness of 20 nm. The dopant is doped by 90:10 by weight of CBP [4,4'-N, N'-dicarbazole-biphenyl] as a light emitting layer host and Ir (ppy) 3 [tris (2-phenylpyridine) -iridium] as a dopant. A light emitting layer having a thickness of 30 nm was deposited on the hole transport layer. Subsequently, (1,1'-bisphenyl) -4-oleato) bis (2-methyl-8-quinolineoleito) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm with a hole blocking layer, Tris (8-quinolinol) aluminum (hereinafter abbreviated to Alq 3 ) was formed into a transport layer to a thickness of 40 nm. Thereafter, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm as an electron injection layer, and then, Al was deposited to a thickness of 150 nm to use an organic light emitting device.
[[
비교예Comparative example
1] One]
상기 실시예 6과 동일하게 유기전계 발광소자를 제작하되, 본 발명의 화합물 대신 하기 비교 화합물 1을 이용하여 정공수송층을 형성하였다.An organic light emitting diode was manufactured in the same manner as in Example 6, but the hole transport layer was formed using the following Comparative Compound 1 instead of the compound of the present invention.
<비교 화합물 1> <Comparative Compound 1>
이와 같이 제조된 실시예 및 비교예 유기전기발광소자에 순바이어스 직류전압을 가하여 포토리서치(photoresearch)사의 PR-650으로 전기발광(EL) 특성을 측정하였으며, 그 측정 결과 300cd/m2 기준 휘도에서 맥사이언스사에서 제조된 수명 측정 장비를 통해 T90 수명을 측정하였다.The electroluminescent (EL) characteristics of the Example and Comparative Example organic electroluminescent devices manufactured as described above were applied to the PR-650 of photoresearch by applying a forward bias DC voltage, and the measured results were measured at 300 cd / m 2 reference luminance. The T90 life was measured using a life measurement instrument manufactured by McScience.
하기 표 5은 본 발명에 따른 화합물을 적용한 실시예 및 비교예에 대한 소자제작 및 그 평가 결과를 나타낸다.Table 5 below shows device fabrication and evaluation results of Examples and Comparative Examples to which the compound according to the present invention is applied.
표 5
Table 5
| 화합물 | 구동전압 | 전류(mA/cm2) | 휘도(cd/m2) | 효율(cd/A) | T(90) | |
| 비교예(1) | 비교 화합물 1 | 6.2 | 7.9 | 300.0 | 3.8 | 78 |
| 실시예(1) | 화합물(1-1) | 5.3 | 5.7 | 300.0 | 5.3 | 126.7 |
| 실시예(2) | 화합물(1-2) | 5.3 | 5.5 | 300.0 | 5.4 | 104.1 |
| 실시예(3) | 화합물(1-3) | 5.6 | 6.7 | 300.0 | 4.5 | 122.3 |
| 실시예(4) | 화합물(1-4) | 5.1 | 5.6 | 300.0 | 5.3 | 126.5 |
| 실시예(5) | 화합물(1-5) | 4.8 | 5.1 | 300.0 | 5.8 | 130.9 |
| 실시예(6) | 화합물(1-6) | 4.8 | 5.1 | 300.0 | 5.9 | 142.0 |
| 실시예(7) | 화합물(1-7) | 5.3 | 5.3 | 300.0 | 5.6 | 119.5 |
| 실시예(8) | 화합물(1-8) | 5.3 | 5.9 | 300.0 | 5.1 | 96.8 |
| 실시예(9) | 화합물(1-9) | 5.2 | 5.4 | 300.0 | 5.5 | 99.0 |
| 실시예(10) | 화합물(1-10) | 5.4 | 6.2 | 300.0 | 4.8 | 129.4 |
| 실시예(11) | 화합물(1-11) | 5.4 | 8.0 | 300.0 | 3.7 | 95.8 |
| 실시예(12) | 화합물(1-12) | 5.0 | 5.8 | 300.0 | 5.2 | 96.5 |
| 실시예(13) | 화합물(1-13) | 5.7 | 7.1 | 300.0 | 4.2 | 122.0 |
| 실시예(14) | 화합물(1-14) | 4.8 | 5.0 | 300.0 | 6.0 | 124.6 |
| 실시예(15) | 화합물(1-15) | 5.1 | 5.2 | 300.0 | 5.8 | 107.2 |
| 실시예(16) | 화합물(1-16) | 5.2 | 6.8 | 300.0 | 4.4 | 128.4 |
| 실시예(17) | 화합물(1-17) | 5.7 | 7.9 | 300.0 | 3.8 | 125.9 |
| 실시예(18) | 화합물(1-18) | 5.2 | 10.0 | 300.0 | 3.0 | 108.2 |
| 실시예(19) | 화합물(1-19) | 5.0 | 5.1 | 300.0 | 5.9 | 111.9 |
| 실시예(20) | 화합물(1-20) | 5.2 | 9.7 | 300.0 | 3.1 | 97.1 |
| 실시예(21) | 화합물(1-21) | 5.7 | 5.7 | 300.0 | 5.3 | 118.0 |
| 실시예(22) | 화합물(1-22) | 5.6 | 5.2 | 300.0 | 5.7 | 122.3 |
| 실시예(23) | 화합물(1-23) | 5.1 | 9.2 | 300.0 | 3.3 | 121.0 |
| 실시예(24) | 화합물(1-24) | 5.6 | 6.4 | 300.0 | 4.7 | 107.1 |
| 실시예(25) | 화합물(1-25) | 5.1 | 9.3 | 300.0 | 3.2 | 113.3 |
| 실시예(26) | 화합물(1-26) | 5.3 | 8.3 | 300.0 | 3.6 | 119.4 |
| 실시예(27) | 화합물(1-27) | 5.8 | 9.8 | 300.0 | 3.1 | 97.1 |
| 실시예(28) | 화합물(1-28) | 5.9 | 6.3 | 300.0 | 4.7 | 99.9 |
| 실시예(29) | 화합물(1-29) | 5.7 | 7.8 | 300.0 | 3.9 | 106.4 |
| 실시예(30) | 화합물(1-30) | 5.1 | 9.0 | 300.0 | 3.3 | 96.0 |
| 실시예(31) | 화합물(1-31) | 5.7 | 9.3 | 300.0 | 3.2 | 115.0 |
| 실시예(32) | 화합물(1-32) | 5.3 | 7.0 | 300.0 | 4.3 | 122.3 |
| 실시예(33) | 화합물(1-33) | 5.5 | 8.4 | 300.0 | 3.6 | 103.8 |
| 실시예(34) | 화합물(1-34) | 5.3 | 6.8 | 300.0 | 4.4 | 112.5 |
| 실시예(35) | 화합물(1-35) | 5.6 | 7.2 | 300.0 | 4.1 | 110.2 |
| 실시예(36) | 화합물(1-36) | 5.0 | 5.4 | 300.0 | 5.6 | 98.2 |
| 실시예(37) | 화합물(1-37) | 5.7 | 6.1 | 300.0 | 4.9 | 92.1 |
| 실시예(38) | 화합물(1-38) | 5.7 | 6.5 | 300.0 | 4.6 | 117.1 |
| 실시예(39) | 화합물(1-39) | 5.1 | 7.3 | 300.0 | 4.1 | 114.3 |
| 실시예(40) | 화합물(1-40) | 5.5 | 6.1 | 300.0 | 4.9 | 108.0 |
| 실시예(41) | 화합물(1-41) | 5.3 | 6.2 | 300.0 | 4.9 | 98.5 |
| 실시예(42) | 화합물(1-42) | 5.1 | 5.8 | 300.0 | 5.2 | 108.8 |
| 실시예(43) | 화합물(1-43) | 5.3 | 5.9 | 300.0 | 5.1 | 116.8 |
| 실시예(44) | 화합물(1-44) | 5.4 | 6.0 | 300.0 | 5.0 | 110.8 |
| 실시예(45) | 화합물(1-45) | 5.8 | 5.3 | 300.0 | 5.7 | 128.7 |
| 실시예(46) | 화합물(1-46) | 5.6 | 6.4 | 300.0 | 4.7 | 108.6 |
| 실시예(47) | 화합물(1-47) | 5.0 | 8.5 | 300.0 | 3.5 | 94.7 |
| 실시예(48) | 화합물(1-48) | 5.2 | 5.9 | 300.0 | 5.1 | 91.7 |
| 실시예(49) | 화합물(1-49) | 5.5 | 6.9 | 300.0 | 4.3 | 121.1 |
| 실시예(50) | 화합물(1-50) | 5.5 | 8.8 | 300.0 | 3.4 | 90.2 |
| 실시예(51) | 화합물(1-51) | 5.0 | 8.4 | 300.0 | 3.6 | 118.5 |
| 실시예(52) | 화합물(1-52) | 5.8 | 6.4 | 300.0 | 4.7 | 123.4 |
| 실시예(53) | 화합물(1-53) | 5.4 | 6.9 | 300.0 | 4.4 | 114.8 |
| 실시예(54) | 화합물(1-54) | 5.7 | 5.2 | 300.0 | 5.7 | 109.9 |
| 실시예(55) | 화합물(1-55) | 5.8 | 6.7 | 300.0 | 4.5 | 115.6 |
| 실시예(56) | 화합물(1-56) | 5.6 | 5.4 | 300.0 | 5.5 | 126.8 |
| 실시예(57) | 화합물(1-57) | 5.8 | 9.5 | 300.0 | 3.2 | 97.1 |
| 실시예(58) | 화합물(1-58) | 5.8 | 7.2 | 300.0 | 4.2 | 99.4 |
| 실시예(59) | 화합물(1-59) | 5.5 | 7.7 | 300.0 | 3.9 | 113.2 |
| 실시예(60) | 화합물(1-60) | 5.8 | 5.4 | 300.0 | 5.5 | 111.5 |
| 실시예(61) | 화합물(1-61) | 5.0 | 6.5 | 300.0 | 4.6 | 126.2 |
| 실시예(62) | 화합물(1-62) | 5.4 | 7.4 | 300.0 | 4.0 | 123.4 |
| 실시예(63) | 화합물(1-63) | 5.7 | 9.5 | 300.0 | 3.2 | 103.7 |
| 실시예(64) | 화합물(1-64) | 5.1 | 6.2 | 300.0 | 4.9 | 104.5 |
| 실시예(65) | 화합물(1-65) | 5.3 | 6.1 | 300.0 | 5.0 | 114.7 |
| 실시예(66) | 화합물(1-66) | 5.0 | 9.2 | 300.0 | 3.3 | 128.3 |
| 실시예(67) | 화합물(1-67) | 5.7 | 6.6 | 300.0 | 4.6 | 121.3 |
| 실시예(68) | 화합물(1-68) | 5.2 | 5.3 | 300.0 | 5.7 | 119.2 |
| 실시예(69) | 화합물(1-69) | 5.4 | 7.3 | 300.0 | 4.1 | 109.5 |
| 실시예(70) | 화합물(1-70) | 5.4 | 6.6 | 300.0 | 4.5 | 110.7 |
| 실시예(71) | 화합물(1-71) | 5.8 | 5.6 | 300.0 | 5.3 | 92.0 |
| 실시예(72) | 화합물(1-72) | 4.9 | 5.1 | 300.0 | 5.9 | 104.3 |
| 실시예(73) | 화합물(1-73) | 5.1 | 9.3 | 300.0 | 3.2 | 92.4 |
| 실시예(74) | 화합물(1-74) | 5.0 | 6.4 | 300.0 | 4.7 | 93.6 |
| 실시예(75) | 화합물(1-75) | 5.0 | 8.7 | 300.0 | 3.5 | 98.7 |
| 실시예(76) | 화합물(1-76) | 5.1 | 5.5 | 300.0 | 5.5 | 118.2 |
| 실시예(77) | 화합물(1-77) | 5.0 | 8.7 | 300.0 | 3.4 | 94.5 |
| 실시예(78) | 화합물(1-78) | 5.1 | 7.8 | 300.0 | 3.8 | 105.1 |
| 실시예(79) | 화합물(1-79) | 5.0 | 5.2 | 300.0 | 5.7 | 123.3 |
| 실시예(80) | 화합물(1-80) | 5.0 | 5.9 | 300.0 | 5.1 | 100.9 |
| 실시예(81) | 화합물(1-81) | 5.1 | 8.4 | 300.0 | 3.6 | 118.3 |
| 실시예(82) | 화합물(1-82) | 5.1 | 6.7 | 300.0 | 4.5 | 113.7 |
| 실시예(83) | 화합물(1-83) | 5.0 | 9.9 | 300.0 | 3.0 | 97.1 |
| 실시예(84) | 화합물(1-84) | 5.3 | 8.5 | 300.0 | 3.5 | 114.9 |
| 실시예(85) | 화합물(1-85) | 5.1 | 7.2 | 300.0 | 4.2 | 111.3 |
| 실시예(86) | 화합물(1-86) | 5.2 | 8.8 | 300.0 | 3.4 | 91.7 |
| 실시예(87) | 화합물(1-87) | 5.5 | 6.8 | 300.0 | 4.4 | 96.5 |
| 실시예(88) | 화합물(1-88) | 5.3 | 5.7 | 300.0 | 5.3 | 104.9 |
| 실시예(89) | 화합물(1-89) | 5.3 | 7.0 | 300.0 | 4.3 | 123.1 |
| 실시예(90) | 화합물(1-90) | 5.3 | 5.8 | 300.0 | 5.2 | 103.3 |
| 실시예(91) | 화합물(1-91) | 5.8 | 8.1 | 300.0 | 3.7 | 91.0 |
| 실시예(92) | 화합물(1-92) | 5.6 | 9.0 | 300.0 | 3.3 | 109.1 |
| 실시예(93) | 화합물(1-93) | 5.3 | 5.5 | 300.0 | 5.4 | 119.6 |
| 실시예(94) | 화합물(1-94) | 5.8 | 7.5 | 300.0 | 4.0 | 95.4 |
| 실시예(95) | 화합물(1-95) | 5.5 | 7.2 | 300.0 | 4.2 | 90.2 |
| 실시예(96) | 화합물(1-96) | 5.8 | 8.5 | 300.0 | 3.5 | 96.5 |
| 실시예(97) | 화합물(1-97) | 5.2 | 5.4 | 300.0 | 5.5 | 103.3 |
| 실시예(98) | 화합물(1-98) | 5.5 | 5.8 | 300.0 | 5.1 | 96.5 |
| 실시예(99) | 화합물(1-99) | 5.8 | 5.7 | 300.0 | 5.2 | 115.7 |
| 실시예(100) | 화합물(1-100) | 5.1 | 9.1 | 300.0 | 3.3 | 109.7 |
| 실시예(101) | 화합물(1-101) | 5.4 | 9.7 | 300.0 | 3.1 | 117.8 |
| 실시예(102) | 화합물(1-102) | 5.5 | 8.7 | 300.0 | 3.4 | 97.0 |
| 실시예(103) | 화합물(1-103) | 5.5 | 7.1 | 300.0 | 4.2 | 124.3 |
| 실시예(104) | 화합물(1-104) | 5.3 | 9.9 | 300.0 | 3.0 | 119.0 |
| 실시예(105) | 화합물(1-105) | 5.3 | 5.5 | 300.0 | 5.5 | 91.2 |
| 실시예(106) | 화합물(1-106) | 5.3 | 7.4 | 300.0 | 4.0 | 96.9 |
| 실시예(107) | 화합물(1-107) | 5.1 | 5.8 | 300.0 | 5.1 | 91.3 |
| 실시예(108) | 화합물(1-108) | 5.0 | 5.6 | 300.0 | 5.3 | 111.6 |
| 실시예(109) | 화합물(1-109) | 5.4 | 7.7 | 300.0 | 3.9 | 98.8 |
| 실시예(110) | 화합물(1-110) | 5.3 | 9.2 | 300.0 | 3.2 | 114.4 |
| 실시예(111) | 화합물(1-111) | 5.3 | 9.1 | 300.0 | 3.3 | 92.5 |
| 실시예(112) | 화합물(1-112) | 5.1 | 5.6 | 300.0 | 5.3 | 95.0 |
| 실시예(113) | 화합물(1-113) | 5.2 | 8.8 | 300.0 | 3.4 | 128.2 |
| 실시예(114) | 화합물(1-114) | 5.3 | 8.0 | 300.0 | 3.7 | 127.9 |
| 실시예(115) | 화합물(1-115) | 5.3 | 7.0 | 300.0 | 4.3 | 122.0 |
| 실시예(116) | 화합물(1-116) | 5.2 | 8.0 | 300.0 | 3.7 | 112.8 |
| 실시예(117) | 화합물(1-117) | 5.4 | 6.3 | 300.0 | 4.8 | 130.0 |
| 실시예(118) | 화합물(1-118) | 5.4 | 7.8 | 300.0 | 3.9 | 112.6 |
| 실시예(119) | 화합물(1-119) | 5.4 | 9.8 | 300.0 | 3.0 | 91.1 |
| 실시예(120) | 화합물(1-120) | 5.3 | 9.2 | 300.0 | 3.3 | 97.5 |
| 실시예(121) | 화합물(1-121) | 5.2 | 5.3 | 300.0 | 5.6 | 99.2 |
| 실시예(122) | 화합물(1-122) | 5.2 | 5.5 | 300.0 | 5.4 | 124.6 |
| 실시예(123) | 화합물(1-123) | 5.3 | 5.7 | 300.0 | 5.3 | 110.3 |
| 실시예(124) | 화합물(1-124) | 5.5 | 6.1 | 300.0 | 4.9 | 129.0 |
| 실시예(125) | 화합물(1-125) | 5.8 | 6.2 | 300.0 | 4.8 | 115.2 |
| 실시예(126) | 화합물(1-126) | 5.3 | 6.1 | 300.0 | 4.9 | 99.6 |
| 실시예(127) | 화합물(1-127) | 5.4 | 6.5 | 300.0 | 4.6 | 124.7 |
| 실시예(128) | 화합물(1-128) | 5.1 | 6.5 | 300.0 | 4.6 | 104.3 |
| 실시예(129) | 화합물(1-129) | 5.7 | 5.3 | 300.0 | 5.6 | 118.2 |
| 실시예(130) | 화합물(1-130) | 5.1 | 6.9 | 300.0 | 4.4 | 104.7 |
| 실시예(131) | 화합물(1-131) | 5.2 | 7.0 | 300.0 | 4.3 | 124.2 |
| 실시예(132) | 화합물(1-132) | 5.1 | 8.3 | 300.0 | 3.6 | 103.1 |
| 실시예(133) | 화합물(1-133) | 5.8 | 9.6 | 300.0 | 3.1 | 122.8 |
| 실시예(134) | 화합물(1-134) | 5.2 | 5.7 | 300.0 | 5.3 | 123.6 |
| 실시예(135) | 화합물(1-135) | 5.5 | 5.3 | 300.0 | 5.7 | 117.5 |
| 실시예(136) | 화합물(1-136) | 5.1 | 8.2 | 300.0 | 3.6 | 109.7 |
| 실시예(137) | 화합물(1-137) | 5.6 | 6.9 | 300.0 | 4.4 | 108.4 |
| 실시예(138) | 화합물(1-138) | 5.2 | 6.3 | 300.0 | 4.8 | 123.5 |
| 실시예(139) | 화합물(1-139) | 5.6 | 9.2 | 300.0 | 3.2 | 91.5 |
| 실시예(140) | 화합물(1-140) | 5.8 | 7.3 | 300.0 | 4.1 | 123.8 |
| 실시예(141) | 화합물(1-141) | 5.9 | 8.1 | 300.0 | 3.7 | 123.3 |
| 실시예(142) | 화합물(1-142) | 5.2 | 8.5 | 300.0 | 3.5 | 111.7 |
| 실시예(143) | 화합물(1-143) | 5.4 | 6.1 | 300.0 | 4.9 | 93.5 |
| 실시예(144) | 화합물(1-144) | 5.0 | 5.8 | 300.0 | 5.2 | 111.7 |
| 실시예(145) | 화합물(1-145) | 5.8 | 5.9 | 300.0 | 5.1 | 113.6 |
| 실시예(146) | 화합물(1-146) | 5.5 | 5.9 | 300.0 | 5.1 | 97.4 |
| 실시예(147) | 화합물(1-147) | 5.6 | 6.2 | 300.0 | 4.8 | 112.4 |
| 실시예(148) | 화합물(1-148) | 5.8 | 9.4 | 300.0 | 3.2 | 90.0 |
| 실시예(149) | 화합물(1-149) | 5.1 | 6.2 | 300.0 | 4.9 | 99.7 |
| 실시예(150) | 화합물(1-150) | 5.8 | 5.4 | 300.0 | 5.5 | 96.8 |
| 실시예(151) | 화합물(3-1) | 5.0 | 6.6 | 300.0 | 4.5 | 100.1 |
| 실시예(152) | 화합물(3-2) | 5.4 | 9.6 | 300.0 | 3.1 | 116.4 |
| 실시예(153) | 화합물(3-4) | 5.6 | 5.8 | 300.0 | 5.2 | 118.2 |
| 실시예(154) | 화합물(3-4) | 5.1 | 9.1 | 300.0 | 3.3 | 94.5 |
| 실시예(155) | 화합물(3-9) | 5.3 | 5.7 | 300.0 | 5.3 | 97.2 |
| 실시예(156) | 화합물(3-10) | 5.5 | 9.0 | 300.0 | 3.3 | 94.7 |
| 실시예(157) | 화합물(3-11) | 5.4 | 8.2 | 300.0 | 3.7 | 102.4 |
| 실시예(158) | 화합물(3-13) | 5.0 | 8.7 | 300.0 | 3.4 | 94.4 |
| 실시예(159) | 화합물(3-14) | 5.4 | 7.3 | 300.0 | 4.1 | 91.3 |
| 실시예(160) | 화합물(3-15) | 4.9 | 7.7 | 300.0 | 3.9 | 100.0 |
| 실시예(161) | 화합물(3-16) | 5.6 | 9.4 | 300.0 | 3.2 | 117.1 |
| 실시예(162) | 화합물(3-20) | 5.3 | 6.6 | 300.0 | 4.6 | 117.6 |
| 실시예(163) | 화합물(3-21) | 5.1 | 6.2 | 300.0 | 4.8 | 90.1 |
| 실시예(164) | 화합물(3-23) | 5.1 | 7.5 | 300.0 | 4.0 | 110.7 |
| 실시예(165) | 화합물(3-24) | 5.3 | 9.6 | 300.0 | 3.1 | 100.2 |
| 실시예(166) | 화합물(3-25) | 5.1 | 9.4 | 300.0 | 3.2 | 95.1 |
| 실시예(167) | 화합물(3-26) | 5.1 | 6.6 | 300.0 | 4.5 | 114.6 |
| 실시예(168) | 화합물(3-29) | 4.9 | 5.9 | 300.0 | 5.1 | 115.6 |
| 실시예(169) | 화합물(3-30) | 5.4 | 7.3 | 300.0 | 4.1 | 104.7 |
| 실시예(170) | 화합물(3-31) | 5.5 | 9.1 | 300.0 | 3.3 | 110.9 |
| 실시예(171) | 화합물(3-34) | 5.0 | 9.4 | 300.0 | 3.2 | 103.8 |
| 실시예(172) | 화합물(3-35) | 5.1 | 6.9 | 300.0 | 4.4 | 110.2 |
| 실시예(173) | 화합물(3-49) | 5.5 | 6.6 | 300.0 | 4.6 | 103.3 |
| 실시예(174) | 화합물(3-50) | 4.9 | 9.0 | 300.0 | 3.3 | 115.1 |
| 실시예(175) | 화합물(3-58) | 5.6 | 6.0 | 300.0 | 5.0 | 93.2 |
| 실시예(176) | 화합물(3-60) | 5.0 | 6.2 | 300.0 | 4.9 | 118.4 |
| 실시예(177) | 화합물(3-61) | 5.5 | 7.6 | 300.0 | 3.9 | 92.6 |
| 실시예(178) | 화합물(3-66) | 5.5 | 7.3 | 300.0 | 4.1 | 105.5 |
| 실시예(179) | 화합물(3-68) | 5.4 | 8.0 | 300.0 | 3.7 | 99.1 |
| 실시예(180) | 화합물(3-69) | 5.4 | 7.5 | 300.0 | 4.0 | 91.9 |
| 실시예(181) | 화합물(3-70) | 5.3 | 6.8 | 300.0 | 4.4 | 92.5 |
| 실시예(182) | 화합물(3-71) | 5.1 | 6.7 | 300.0 | 4.5 | 104.8 |
| 실시예(183) | 화합물(3-72) | 5.1 | 6.3 | 300.0 | 4.8 | 111.4 |
| 실시예(184) | 화합물(4-4) | 4.9 | 6.7 | 300.0 | 4.5 | 94.2 |
| 실시예(185) | 화합물(4-7) | 5.2 | 8.0 | 300.0 | 3.8 | 102.0 |
| 실시예(186) | 화합물(4-8) | 4.9 | 7.3 | 300.0 | 4.1 | 105.4 |
| 실시예(187) | 화합물(4-9) | 4.7 | 7.0 | 300.0 | 4.3 | 105.3 |
| 실시예(188) | 화합물(4-10) | 4.6 | 6.7 | 300.0 | 4.5 | 94.0 |
| 실시예(189) | 화합물(4-11) | 5.2 | 9.2 | 300.0 | 3.2 | 93.4 |
| 실시예(190) | 화합물(4-24) | 4.8 | 6.3 | 300.0 | 4.7 | 99.9 |
| 실시예(191) | 화합물(4-25) | 5.0 | 8.9 | 300.0 | 3.4 | 98.4 |
| 실시예(192) | 화합물(4-27) | 5.0 | 6.6 | 300.0 | 4.5 | 99.4 |
| 실시예(193) | 화합물(4-32) | 5.0 | 5.8 | 300.0 | 5.2 | 91.4 |
| 실시예(194) | 화합물(4-33) | 4.6 | 6.0 | 300.0 | 5.0 | 95.3 |
| 실시예(195) | 화합물(4-36) | 4.6 | 6.1 | 300.0 | 4.9 | 105.1 |
| 실시예(196) | 화합물(4-43) | 4.8 | 5.8 | 300.0 | 5.2 | 96.0 |
| 실시예(197) | 화합물(4-44) | 4.5 | 6.3 | 300.0 | 4.8 | 90.2 |
| 실시예(198) | 화합물(4-45) | 4.3 | 6.5 | 300.0 | 4.6 | 103.4 |
| 실시예(199) | 화합물(4-47) | 5.1 | 7.0 | 300.0 | 4.3 | 92.5 |
| 실시예(200) | 화합물(4-48) | 4.9 | 6.7 | 300.0 | 4.5 | 96.4 |
| 실시예(201) | 화합물(4-55) | 5.1 | 6.9 | 300.0 | 4.3 | 98.5 |
| 실시예(202) | 화합물(4-58) | 4.8 | 6.2 | 300.0 | 4.8 | 105.0 |
| 실시예(203) | 화합물(4-61) | 4.9 | 7.7 | 300.0 | 3.9 | 105.8 |
| 실시예(204) | 화합물(4-62) | 5.0 | 8.8 | 300.0 | 3.4 | 102.7 |
| 실시예(205) | 화합물(4-63) | 4.9 | 7.5 | 300.0 | 4.0 | 97.3 |
| 실시예(206) | 화합물(4-64) | 5.2 | 6.7 | 300.0 | 4.5 | 108.4 |
| 실시예(207) | 화합물(4-65) | 4.9 | 5.7 | 300.0 | 5.3 | 100.4 |
| 실시예(208) | 화합물(4-66) | 5.1 | 7.0 | 300.0 | 4.3 | 105.8 |
| 실시예(209) | 화합물(4-67) | 5.3 | 7.7 | 300.0 | 3.9 | 101.3 |
| 실시예(210) | 화합물(4-68) | 4.9 | 6.4 | 300.0 | 4.7 | 102.2 |
| 실시예(211) | 화합물(4-69) | 4.8 | 8.2 | 300.0 | 3.6 | 93.2 |
| 실시예(212) | 화합물(4-70) | 5.2 | 6.2 | 300.0 | 4.8 | 106.1 |
| 실시예(213) | 화합물(4-71) | 4.8 | 8.8 | 300.0 | 3.4 | 95.2 |
| 실시예(214) | 화합물(4-104) | 5.3 | 7.6 | 300.0 | 3.9 | 108.3 |
| 실시예(215) | 화합물(4-105) | 5.1 | 7.9 | 300.0 | 3.8 | 103.7 |
| 실시예(216) | 화합물(4-106) | 5.0 | 8.5 | 300.0 | 3.5 | 108.6 |
| 실시예(217) | 화합물(4-107) | 5.1 | 6.7 | 300.0 | 4.4 | 103.3 |
| 실시예(218) | 화합물(4-108) | 5.2 | 9.7 | 300.0 | 3.1 | 92.2 |
| 실시예(219) | 화합물(5-2) | 5.3 | 8.7 | 300.0 | 3.5 | 90.8 |
| 실시예(220) | 화합물(5-4) | 5.3 | 5.8 | 300.0 | 5.2 | 101.7 |
| 실시예(221) | 화합물(5-6) | 5.3 | 9.5 | 300.0 | 3.2 | 98.9 |
| 실시예(222) | 화합물(5-7) | 5.4 | 5.7 | 300.0 | 5.3 | 93.0 |
| 실시예(223) | 화합물(5-10) | 5.5 | 6.1 | 300.0 | 4.9 | 106.5 |
| 실시예(224) | 화합물(5-11) | 5.4 | 8.9 | 300.0 | 3.4 | 92.8 |
| 실시예(225) | 화합물(5-12) | 5.3 | 6.7 | 300.0 | 4.5 | 97.9 |
| 실시예(226) | 화합물(5-16) | 5.1 | 6.9 | 300.0 | 4.3 | 101.9 |
| 실시예(227) | 화합물(5-17) | 5.0 | 8.3 | 300.0 | 3.6 | 103.7 |
| 실시예(228) | 화합물(5-18) | 5.2 | 7.6 | 300.0 | 4.0 | 104.7 |
| 실시예(229) | 화합물(5-19) | 4.8 | 5.9 | 300.0 | 5.1 | 96.9 |
| 실시예(230) | 화합물(5-20) | 4.7 | 6.6 | 300.0 | 4.6 | 98.1 |
| 실시예(231) | 화합물(5-21) | 4.8 | 6.5 | 300.0 | 4.6 | 102.4 |
| 실시예(232) | 화합물(5-22) | 5.0 | 6.2 | 300.0 | 4.9 | 103.7 |
| 실시예(233) | 화합물(5-23) | 5.2 | 7.2 | 300.0 | 4.2 | 109.3 |
| 실시예(234) | 화합물(5-24) | 4.9 | 5.9 | 300.0 | 5.0 | 96.7 |
| 실시예(235) | 화합물(5-27) | 5.5 | 9.0 | 300.0 | 3.3 | 91.3 |
| 실시예(236) | 화합물(5-28) | 5.6 | 9.0 | 300.0 | 3.3 | 92.3 |
| 실시예(237) | 화합물(5-30) | 5.4 | 5.8 | 300.0 | 5.2 | 98.6 |
| 실시예(238) | 화합물(5-32) | 5.5 | 7.6 | 300.0 | 4.0 | 98.2 |
| 실시예(239) | 화합물(5-33) | 5.4 | 8.1 | 300.0 | 3.7 | 104.1 |
| 실시예(240) | 화합물(5-34) | 4.9 | 6.1 | 300.0 | 4.9 | 105.0 |
| 실시예(241) | 화합물(5-36) | 5.4 | 7.0 | 300.0 | 4.3 | 102.2 |
| 실시예(242) | 화합물(5-37) | 5.1 | 6.0 | 300.0 | 5.0 | 96.6 |
| 실시예(243) | 화합물(5-38) | 4.9 | 7.6 | 300.0 | 4.0 | 90.6 |
| 실시예(244) | 화합물(5-40) | 5.4 | 6.4 | 300.0 | 4.7 | 105.2 |
| 실시예(245) | 화합물(5-41) | 4.9 | 6.7 | 300.0 | 4.5 | 93.9 |
| 실시예(246) | 화합물(5-42) | 5.4 | 7.4 | 300.0 | 4.1 | 101.1 |
| 실시예(247) | 화합물(5-43) | 5.5 | 8.0 | 300.0 | 3.7 | 102.9 |
| 실시예(248) | 화합물(5-44) | 5.6 | 5.7 | 300.0 | 5.3 | 94.0 |
| 실시예(249) | 화합물(5-45) | 4.8 | 9.4 | 300.0 | 3.2 | 99.3 |
| 실시예(250) | 화합물(5-47) | 5.3 | 8.3 | 300.0 | 3.6 | 109.2 |
| 실시예(251) | 화합물(5-49) | 5.2 | 6.5 | 300.0 | 4.6 | 103.3 |
| 실시예(252) | 화합물(5-50) | 5.0 | 6.2 | 300.0 | 4.8 | 106.2 |
| 실시예(253) | 화합물(5-51) | 5.3 | 6.2 | 300.0 | 4.8 | 98.8 |
| 실시예(254) | 화합물(6-10) | 5.4 | 9.6 | 300.0 | 3.1 | 91.4 |
| 실시예(255) | 화합물(6-11) | 5.2 | 7.4 | 300.0 | 4.1 | 104.4 |
| 실시예(256) | 화합물(6-12) | 5.3 | 6.2 | 300.0 | 4.8 | 90.2 |
| 실시예(257) | 화합물(6-13) | 5.7 | 6.8 | 300.0 | 4.4 | 105.9 |
| 실시예(258) | 화합물(6-14) | 5.4 | 6.3 | 300.0 | 4.8 | 103.5 |
| 실시예(259) | 화합물(6-15) | 5.4 | 6.5 | 300.0 | 4.6 | 111.5 |
| 실시예(260) | 화합물(6-16) | 5.2 | 6.7 | 300.0 | 4.4 | 109.9 |
| 실시예(261) | 화합물(6-17) | 5.4 | 9.4 | 300.0 | 3.2 | 101.4 |
| 실시예(262) | 화합물(6-18) | 5.5 | 5.7 | 300.0 | 5.3 | 110.0 |
| 실시예(263) | 화합물(6-19) | 5.5 | 6.1 | 300.0 | 4.9 | 111.3 |
| 실시예(264) | 화합물(6-20) | 5.3 | 9.2 | 300.0 | 3.3 | 110.0 |
| 실시예(265) | 화합물(6-21) | 5.2 | 7.2 | 300.0 | 4.2 | 98.8 |
| 실시예(266) | 화합물(6-22) | 5.7 | 6.3 | 300.0 | 4.7 | 97.0 |
| 실시예(267) | 화합물(6-23) | 5.6 | 6.8 | 300.0 | 4.4 | 96.2 |
| 실시예(268) | 화합물(6-24) | 5.6 | 6.6 | 300.0 | 4.6 | 90.9 |
| 실시예(269) | 화합물(6-28) | 5.6 | 7.1 | 300.0 | 4.2 | 116.5 |
| 실시예(270) | 화합물(6-32) | 5.8 | 9.9 | 300.0 | 3.0 | 90.2 |
| 실시예(271) | 화합물(6-33) | 5.4 | 6.4 | 300.0 | 4.7 | 99.7 |
| 실시예(272) | 화합물(6-39) | 5.3 | 7.0 | 300.0 | 4.3 | 95.8 |
| 실시예(273) | 화합물(6-40) | 5.6 | 7.3 | 300.0 | 4.1 | 111.7 |
| 실시예(274) | 화합물(6-41) | 5.7 | 8.5 | 300.0 | 3.5 | 96.2 |
| 실시예(275) | 화합물(6-43) | 5.6 | 6.7 | 300.0 | 4.5 | 92.2 |
| 실시예(276) | 화합물(6-47) | 5.5 | 5.7 | 300.0 | 5.3 | 95.6 |
| 실시예(277) | 화합물(6-49) | 5.5 | 6.8 | 300.0 | 4.4 | 119.5 |
| 실시예(278) | 화합물(6-50) | 5.2 | 7.1 | 300.0 | 4.2 | 101.8 |
| 실시예(279) | 화합물(7-9) | 5.7 | 9.1 | 300.0 | 3.3 | 114.6 |
| 실시예(280) | 화합물(7-10) | 5.8 | 10.0 | 300.0 | 3.0 | 110.4 |
| 실시예(281) | 화합물(7-11) | 5.6 | 6.7 | 300.0 | 4.5 | 100.4 |
| 실시예(282) | 화합물(7-12) | 5.6 | 6.0 | 300.0 | 5.0 | 94.9 |
| 실시예(283) | 화합물(7-14) | 5.8 | 6.8 | 300.0 | 4.4 | 94.9 |
| 실시예(284) | 화합물(7-16) | 5.5 | 7.4 | 300.0 | 4.1 | 94.1 |
| 실시예(285) | 화합물(7-17) | 5.7 | 9.4 | 300.0 | 3.2 | 91.5 |
| 실시예(286) | 화합물(7-19) | 5.7 | 6.0 | 300.0 | 5.0 | 105.0 |
| 실시예(287) | 화합물(7-20) | 5.5 | 9.9 | 300.0 | 3.0 | 104.1 |
| 실시예(288) | 화합물(7-21) | 5.9 | 7.4 | 300.0 | 4.0 | 104.4 |
| 실시예(289) | 화합물(7-22) | 5.6 | 8.0 | 300.0 | 3.8 | 118.1 |
| 실시예(290) | 화합물(7-25) | 5.8 | 9.6 | 300.0 | 3.1 | 108.0 |
| 실시예(291) | 화합물(7-26) | 5.8 | 6.7 | 300.0 | 4.5 | 98.5 |
| 실시예(292) | 화합물(7-27) | 5.7 | 7.8 | 300.0 | 3.8 | 111.9 |
| 실시예(293) | 화합물(7-30) | 5.6 | 6.4 | 300.0 | 4.7 | 92.4 |
| 실시예(294) | 화합물(7-31) | 5.8 | 5.7 | 300.0 | 5.3 | 114.6 |
| 실시예(295) | 화합물(7-36) | 5.8 | 8.9 | 300.0 | 3.4 | 113.0 |
| 실시예(296) | 화합물(7-46) | 5.5 | 8.5 | 300.0 | 3.5 | 116.9 |
| 실시예(297) | 화합물(7-50) | 5.8 | 6.4 | 300.0 | 4.7 | 103.7 |
| 실시예(298) | 화합물(7-51) | 5.8 | 6.2 | 300.0 | 4.8 | 112.2 |
| 실시예(299) | 화합물(7-52) | 5.6 | 8.3 | 300.0 | 3.6 | 94.2 |
| 실시예(300) | 화합물(7-56) | 5.6 | 7.8 | 300.0 | 3.8 | 94.0 |
| 실시예(301) | 화합물(7-61) | 5.6 | 8.8 | 300.0 | 3.4 | 94.3 |
| 실시예(302) | 화합물(7-62) | 5.9 | 6.6 | 300.0 | 4.5 | 103.1 |
| 실시예(303) | 화합물(7-63) | 5.6 | 8.3 | 300.0 | 3.6 | 108.8 |
| 실시예(304) | 화합물(8-1) | 5.2 | 9.5 | 300.0 | 3.2 | 98.5 |
| 실시예(305) | 화합물(8-2) | 5.5 | 6.2 | 300.0 | 4.9 | 110.8 |
| 실시예(306) | 화합물(8-5) | 5.6 | 7.8 | 300.0 | 3.8 | 103.2 |
| 실시예(307) | 화합물(8-6) | 5.4 | 7.2 | 300.0 | 4.2 | 90.7 |
| 실시예(308) | 화합물(8-7) | 5.4 | 7.3 | 300.0 | 4.1 | 103.1 |
| 실시예(309) | 화합물(8-9) | 5.6 | 7.3 | 300.0 | 4.1 | 119.3 |
| 실시예(310) | 화합물(8-10) | 5.3 | 5.9 | 300.0 | 5.1 | 107.6 |
| 실시예(311) | 화합물(8-11) | 5.6 | 5.8 | 300.0 | 5.1 | 95.9 |
| 실시예(312) | 화합물(8-12) | 5.3 | 6.4 | 300.0 | 4.7 | 109.5 |
| 실시예(313) | 화합물(8-16) | 5.2 | 10.0 | 300.0 | 3.0 | 118.9 |
| 실시예(314) | 화합물(8-17) | 5.7 | 8.2 | 300.0 | 3.6 | 118.3 |
| 실시예(315) | 화합물(8-18) | 5.3 | 9.4 | 300.0 | 3.2 | 99.1 |
| 실시예(316) | 화합물(8-20) | 5.2 | 9.8 | 300.0 | 3.1 | 115.4 |
| 실시예(317) | 화합물(8-22) | 5.6 | 7.3 | 300.0 | 4.1 | 103.3 |
| 실시예(318) | 화합물(8-25) | 5.8 | 8.2 | 300.0 | 3.6 | 100.3 |
| 실시예(319) | 화합물(8-26) | 5.6 | 7.0 | 300.0 | 4.3 | 115.9 |
| 실시예(320) | 화합물(8-27) | 5.8 | 7.1 | 300.0 | 4.2 | 108.4 |
| 실시예(321) | 화합물(8-30) | 5.3 | 6.3 | 300.0 | 4.8 | 101.6 |
| 실시예(322) | 화합물(8-31) | 5.6 | 9.9 | 300.0 | 3.0 | 114.0 |
| 실시예(323) | 화합물(8-35) | 5.7 | 6.7 | 300.0 | 4.5 | 106.4 |
| 실시예(324) | 화합물(8-40) | 5.2 | 9.8 | 300.0 | 3.1 | 118.0 |
| 실시예(325) | 화합물(8-47) | 5.4 | 5.7 | 300.0 | 5.2 | 97.0 |
| 실시예(326) | 화합물(8-49) | 5.4 | 5.9 | 300.0 | 5.1 | 104.3 |
| 실시예(327) | 화합물(8-50) | 5.4 | 9.9 | 300.0 | 3.0 | 112.9 |
| 실시예(328) | 화합물(8-51) | 5.3 | 7.0 | 300.0 | 4.3 | 109.0 |
| 실시예(329) | 화합물(8-55) | 5.2 | 7.9 | 300.0 | 3.8 | 90.5 |
| 실시예(330) | 화합물(8-57) | 5.2 | 8.6 | 300.0 | 3.5 | 112.6 |
| 실시예(331) | 화합물(8-58) | 5.7 | 9.8 | 300.0 | 3.1 | 109.1 |
| 실시예(332) | 화합물(8-59) | 5.5 | 7.2 | 300.0 | 4.1 | 101.5 |
| 실시예(333) | 화합물(8-60) | 5.4 | 6.4 | 300.0 | 4.7 | 99.1 |
| 실시예(334) | 화합물(8-61) | 5.6 | 6.9 | 300.0 | 4.4 | 118.6 |
| 실시예(335) | 화합물(9-2) | 5.6 | 6.1 | 300.0 | 4.9 | 98.5 |
| 실시예(336) | 화합물(9-8) | 5.4 | 5.8 | 300.0 | 5.1 | 116.6 |
| 실시예(337) | 화합물(9-11) | 5.5 | 9.4 | 300.0 | 3.2 | 113.9 |
| 실시예(338) | 화합물(9-12) | 5.8 | 6.5 | 300.0 | 4.6 | 95.5 |
| 실시예(339) | 화합물(9-13) | 5.8 | 6.7 | 300.0 | 4.5 | 115.5 |
| 실시예(340) | 화합물(9-14) | 5.5 | 9.2 | 300.0 | 3.3 | 106.5 |
| 실시예(341) | 화합물(9-15) | 5.3 | 6.7 | 300.0 | 4.5 | 116.2 |
| 실시예(342) | 화합물(9-17) | 5.5 | 6.2 | 300.0 | 4.9 | 95.4 |
| 실시예(343) | 화합물(9-18) | 5.8 | 6.0 | 300.0 | 5.0 | 102.5 |
| 실시예(344) | 화합물(9-19) | 5.3 | 5.7 | 300.0 | 5.3 | 118.7 |
| 실시예(345) | 화합물(9-20) | 5.5 | 7.7 | 300.0 | 3.9 | 102.6 |
| 실시예(346) | 화합물(9-21) | 5.3 | 6.8 | 300.0 | 4.4 | 102.3 |
| 실시예(347) | 화합물(9-22) | 5.3 | 8.0 | 300.0 | 3.7 | 91.2 |
| 실시예(348) | 화합물(9-25) | 5.8 | 6.6 | 300.0 | 4.6 | 106.8 |
| 실시예(349) | 화합물(9-27) | 5.7 | 6.6 | 300.0 | 4.6 | 116.0 |
| 실시예(350) | 화합물(9-28) | 5.4 | 5.9 | 300.0 | 5.1 | 94.8 |
| 실시예(351) | 화합물(9-29) | 5.8 | 8.7 | 300.0 | 3.4 | 93.2 |
| 실시예(352) | 화합물(9-30) | 5.3 | 9.9 | 300.0 | 3.0 | 103.9 |
| 실시예(353) | 화합물(9-36) | 5.4 | 9.6 | 300.0 | 3.1 | 108.1 |
| 실시예(354) | 화합물(9-37) | 5.2 | 6.3 | 300.0 | 4.8 | 102.0 |
| 실시예(355) | 화합물(9-38) | 5.4 | 9.1 | 300.0 | 3.3 | 109.1 |
| 실시예(356) | 화합물(9-46) | 5.5 | 6.0 | 300.0 | 5.0 | 92.8 |
| 실시예(357) | 화합물(9-47) | 5.7 | 9.4 | 300.0 | 3.2 | 103.0 |
| 실시예(358) | 화합물(9-49) | 5.5 | 9.4 | 300.0 | 3.2 | 93.4 |
| 실시예(359) | 화합물(9-50) | 5.5 | 6.5 | 300.0 | 4.6 | 98.8 |
| 실시예(360) | 화합물(9-51) | 5.8 | 6.7 | 300.0 | 4.5 | 101.6 |
| 실시예(361) | 화합물(9-53) | 5.2 | 6.6 | 300.0 | 4.5 | 91.6 |
| 실시예(362) | 화합물(9-54) | 5.4 | 6.5 | 300.0 | 4.6 | 109.9 |
| 실시예(363) | 화합물(9-57) | 5.8 | 8.1 | 300.0 | 3.7 | 108.3 |
| 실시예(364) | 화합물(9-58) | 5.4 | 8.6 | 300.0 | 3.5 | 99.3 |
| 실시예(365) | 화합물(10-1) | 5.6 | 6.2 | 300.0 | 4.9 | 100.4 |
| 실시예(366) | 화합물(10-2) | 5.9 | 6.2 | 300.0 | 4.9 | 116.7 |
| 실시예(367) | 화합물(10-4) | 5.7 | 6.2 | 300.0 | 4.8 | 110.5 |
| 실시예(368) | 화합물(10-6) | 5.8 | 7.6 | 300.0 | 4.0 | 113.3 |
| 실시예(369) | 화합물(10-7) | 5.6 | 6.2 | 300.0 | 4.8 | 109.6 |
| 실시예(370) | 화합물(10-8) | 5.7 | 9.4 | 300.0 | 3.2 | 111.8 |
| 실시예(371) | 화합물(10-10) | 5.7 | 6.2 | 300.0 | 4.8 | 97.9 |
| 실시예(372) | 화합물(10-11) | 5.8 | 6.3 | 300.0 | 4.8 | 105.9 |
| 실시예(373) | 화합물(10-12) | 5.5 | 8.1 | 300.0 | 3.7 | 111.5 |
| 실시예(374) | 화합물(10-14) | 5.9 | 5.8 | 300.0 | 5.2 | 94.4 |
| 실시예(375) | 화합물(10-15) | 5.7 | 7.2 | 300.0 | 4.2 | 105.9 |
| 실시예(376) | 화합물(10-16) | 5.8 | 9.0 | 300.0 | 3.3 | 94.0 |
| 실시예(377) | 화합물(10-17) | 5.7 | 7.1 | 300.0 | 4.3 | 116.7 |
| 실시예(378) | 화합물(10-18) | 5.6 | 7.0 | 300.0 | 4.3 | 110.8 |
| 실시예(379) | 화합물(10-19) | 5.7 | 5.9 | 301.0 | 5.1 | 109.0 |
| 실시예(380) | 화합물(10-20) | 5.8 | 7.1 | 302.0 | 4.2 | 90.3 |
| 실시예(381) | 화합물(10-21) | 5.8 | 7.3 | 303.0 | 4.2 | 97.2 |
| 실시예(382) | 화합물(10-22) | 5.6 | 8.8 | 304.0 | 3.5 | 95.4 |
| 실시예(383) | 화합물(10-23) | 5.8 | 8.7 | 305.0 | 3.5 | 93.2 |
| 실시예(384) | 화합물(10-24) | 5.8 | 6.2 | 306.0 | 4.9 | 108.5 |
| 실시예(385) | 화합물(10-45) | 5.7 | 9.4 | 307.0 | 3.3 | 107.9 |
| 실시예(386) | 화합물(10-46) | 5.6 | 6.9 | 308.0 | 4.4 | 119.1 |
| 실시예(387) | 화합물(10-47) | 5.6 | 7.5 | 309.0 | 4.1 | 118.6 |
| 실시예(388) | 화합물(10-48) | 5.8 | 8.1 | 310.0 | 3.8 | 97.6 |
| 실시예(389) | 화합물(10-49) | 5.8 | 10.1 | 311.0 | 3.1 | 92.2 |
| 실시예(390) | 화합물(10-50) | 5.7 | 6.1 | 312.0 | 5.1 | 118.8 |
| compound | Driving voltage | Current (mA / cm2) | Luminance (cd / m2) | Efficiency (cd / A) | T (90) | |
| Comparative Example (1) | Comparative Compound 1 | 6.2 | 7.9 | 300.0 | 3.8 | 78 |
| Example (1) | Compound (1-1) | 5.3 | 5.7 | 300.0 | 5.3 | 126.7 |
| Example (2) | Compound (1-2) | 5.3 | 5.5 | 300.0 | 5.4 | 104.1 |
| Example (3) | Compound (1-3) | 5.6 | 6.7 | 300.0 | 4.5 | 122.3 |
| Example (4) | Compound (1-4) | 5.1 | 5.6 | 300.0 | 5.3 | 126.5 |
| Example (5) | Compound (1-5) | 4.8 | 5.1 | 300.0 | 5.8 | 130.9 |
| Example (6) | Compound (1-6) | 4.8 | 5.1 | 300.0 | 5.9 | 142.0 |
| Example (7) | Compound (1-7) | 5.3 | 5.3 | 300.0 | 5.6 | 119.5 |
| Example (8) | Compound (1-8) | 5.3 | 5.9 | 300.0 | 5.1 | 96.8 |
| Example (9) | Compound (1-9) | 5.2 | 5.4 | 300.0 | 5.5 | 99.0 |
| Example (10) | Compound (1-10) | 5.4 | 6.2 | 300.0 | 4.8 | 129.4 |
| Example (11) | Compound (1-11) | 5.4 | 8.0 | 300.0 | 3.7 | 95.8 |
| Example (12) | Compound (1-12) | 5.0 | 5.8 | 300.0 | 5.2 | 96.5 |
| Example (13) | Compound (1-13) | 5.7 | 7.1 | 300.0 | 4.2 | 122.0 |
| Example (14) | Compound (1-14) | 4.8 | 5.0 | 300.0 | 6.0 | 124.6 |
| Example (15) | Compound (1-15) | 5.1 | 5.2 | 300.0 | 5.8 | 107.2 |
| Example (16) | Compound (1-16) | 5.2 | 6.8 | 300.0 | 4.4 | 128.4 |
| Example (17) | Compound (1-17) | 5.7 | 7.9 | 300.0 | 3.8 | 125.9 |
| Example (18) | Compound (1-18) | 5.2 | 10.0 | 300.0 | 3.0 | 108.2 |
| Example (19) | Compound (1-19) | 5.0 | 5.1 | 300.0 | 5.9 | 111.9 |
| Example (20) | Compound (1-20) | 5.2 | 9.7 | 300.0 | 3.1 | 97.1 |
| Example (21) | Compound (1-21) | 5.7 | 5.7 | 300.0 | 5.3 | 118.0 |
| Example (22) | Compound (1-22) | 5.6 | 5.2 | 300.0 | 5.7 | 122.3 |
| Example (23) | Compound (1-23) | 5.1 | 9.2 | 300.0 | 3.3 | 121.0 |
| Example (24) | Compound (1-24) | 5.6 | 6.4 | 300.0 | 4.7 | 107.1 |
| Example (25) | Compound (1-25) | 5.1 | 9.3 | 300.0 | 3.2 | 113.3 |
| Example (26) | Compound (1-26) | 5.3 | 8.3 | 300.0 | 3.6 | 119.4 |
| Example (27) | Compound (1-27) | 5.8 | 9.8 | 300.0 | 3.1 | 97.1 |
| Example (28) | Compound (1-28) | 5.9 | 6.3 | 300.0 | 4.7 | 99.9 |
| Example (29) | Compound (1-29) | 5.7 | 7.8 | 300.0 | 3.9 | 106.4 |
| Example (30) | Compound (1-30) | 5.1 | 9.0 | 300.0 | 3.3 | 96.0 |
| Example (31) | Compound (1-31) | 5.7 | 9.3 | 300.0 | 3.2 | 115.0 |
| Example (32) | Compound (1-32) | 5.3 | 7.0 | 300.0 | 4.3 | 122.3 |
| Example (33) | Compound (1-33) | 5.5 | 8.4 | 300.0 | 3.6 | 103.8 |
| Example (34) | Compound (1-34) | 5.3 | 6.8 | 300.0 | 4.4 | 112.5 |
| Example (35) | Compound (1-35) | 5.6 | 7.2 | 300.0 | 4.1 | 110.2 |
| Example (36) | Compound (1-36) | 5.0 | 5.4 | 300.0 | 5.6 | 98.2 |
| Example (37) | Compound (1-37) | 5.7 | 6.1 | 300.0 | 4.9 | 92.1 |
| Example (38) | Compound (1-38) | 5.7 | 6.5 | 300.0 | 4.6 | 117.1 |
| Example (39) | Compound (1-39) | 5.1 | 7.3 | 300.0 | 4.1 | 114.3 |
| Example (40) | Compound (1-40) | 5.5 | 6.1 | 300.0 | 4.9 | 108.0 |
| Example (41) | Compound (1-41) | 5.3 | 6.2 | 300.0 | 4.9 | 98.5 |
| Example (42) | Compound (1-42) | 5.1 | 5.8 | 300.0 | 5.2 | 108.8 |
| Example (43) | Compound (1-43) | 5.3 | 5.9 | 300.0 | 5.1 | 116.8 |
| Example (44) | Compound (1-44) | 5.4 | 6.0 | 300.0 | 5.0 | 110.8 |
| Example (45) | Compound (1-45) | 5.8 | 5.3 | 300.0 | 5.7 | 128.7 |
| Example (46) | Compound (1-46) | 5.6 | 6.4 | 300.0 | 4.7 | 108.6 |
| Example (47) | Compound (1-47) | 5.0 | 8.5 | 300.0 | 3.5 | 94.7 |
| Example (48) | Compound (1-48) | 5.2 | 5.9 | 300.0 | 5.1 | 91.7 |
| Example (49) | Compound (1-49) | 5.5 | 6.9 | 300.0 | 4.3 | 121.1 |
| Example (50) | Compound (1-50) | 5.5 | 8.8 | 300.0 | 3.4 | 90.2 |
| Example (51) | Compound (1-51) | 5.0 | 8.4 | 300.0 | 3.6 | 118.5 |
| Example (52) | Compound (1-52) | 5.8 | 6.4 | 300.0 | 4.7 | 123.4 |
| Example (53) | Compound (1-53) | 5.4 | 6.9 | 300.0 | 4.4 | 114.8 |
| Example (54) | Compound (1-54) | 5.7 | 5.2 | 300.0 | 5.7 | 109.9 |
| Example (55) | Compound (1-55) | 5.8 | 6.7 | 300.0 | 4.5 | 115.6 |
| Example (56) | Compound (1-56) | 5.6 | 5.4 | 300.0 | 5.5 | 126.8 |
| Example (57) | Compound (1-57) | 5.8 | 9.5 | 300.0 | 3.2 | 97.1 |
| Example (58) | Compound (1-58) | 5.8 | 7.2 | 300.0 | 4.2 | 99.4 |
| Example (59) | Compound (1-59) | 5.5 | 7.7 | 300.0 | 3.9 | 113.2 |
| Example (60) | Compound (1-60) | 5.8 | 5.4 | 300.0 | 5.5 | 111.5 |
| Example (61) | Compound (1-61) | 5.0 | 6.5 | 300.0 | 4.6 | 126.2 |
| Example (62) | Compound (1-62) | 5.4 | 7.4 | 300.0 | 4.0 | 123.4 |
| Example (63) | Compound (1-63) | 5.7 | 9.5 | 300.0 | 3.2 | 103.7 |
| Example (64) | Compound (1-64) | 5.1 | 6.2 | 300.0 | 4.9 | 104.5 |
| Example (65) | Compound (1-65) | 5.3 | 6.1 | 300.0 | 5.0 | 114.7 |
| Example (66) | Compound (1-66) | 5.0 | 9.2 | 300.0 | 3.3 | 128.3 |
| Example (67) | Compound (1-67) | 5.7 | 6.6 | 300.0 | 4.6 | 121.3 |
| Example (68) | Compound (1-68) | 5.2 | 5.3 | 300.0 | 5.7 | 119.2 |
| Example (69) | Compound (1-69) | 5.4 | 7.3 | 300.0 | 4.1 | 109.5 |
| Example (70) | Compound (1-70) | 5.4 | 6.6 | 300.0 | 4.5 | 110.7 |
| Example (71) | Compound (1-71) | 5.8 | 5.6 | 300.0 | 5.3 | 92.0 |
| Example (72) | Compound (1-72) | 4.9 | 5.1 | 300.0 | 5.9 | 104.3 |
| Example (73) | Compound (1-73) | 5.1 | 9.3 | 300.0 | 3.2 | 92.4 |
| Example (74) | Compound (1-74) | 5.0 | 6.4 | 300.0 | 4.7 | 93.6 |
| Example (75) | Compound (1-75) | 5.0 | 8.7 | 300.0 | 3.5 | 98.7 |
| Example (76) | Compound (1-76) | 5.1 | 5.5 | 300.0 | 5.5 | 118.2 |
| Example (77) | Compound (1-77) | 5.0 | 8.7 | 300.0 | 3.4 | 94.5 |
| Example (78) | Compound (1-78) | 5.1 | 7.8 | 300.0 | 3.8 | 105.1 |
| Example (79) | Compound (1-79) | 5.0 | 5.2 | 300.0 | 5.7 | 123.3 |
| Example (80) | Compound (1-80) | 5.0 | 5.9 | 300.0 | 5.1 | 100.9 |
| Example (81) | Compound (1-81) | 5.1 | 8.4 | 300.0 | 3.6 | 118.3 |
| Example (82) | Compound (1-82) | 5.1 | 6.7 | 300.0 | 4.5 | 113.7 |
| Example (83) | Compound (1-83) | 5.0 | 9.9 | 300.0 | 3.0 | 97.1 |
| Example (84) | Compound (1-84) | 5.3 | 8.5 | 300.0 | 3.5 | 114.9 |
| Example (85) | Compound (1-85) | 5.1 | 7.2 | 300.0 | 4.2 | 111.3 |
| Example (86) | Compound (1-86) | 5.2 | 8.8 | 300.0 | 3.4 | 91.7 |
| Example (87) | Compound (1-87) | 5.5 | 6.8 | 300.0 | 4.4 | 96.5 |
| Example (88) | Compound (1-88) | 5.3 | 5.7 | 300.0 | 5.3 | 104.9 |
| Example (89) | Compound (1-89) | 5.3 | 7.0 | 300.0 | 4.3 | 123.1 |
| Example (90) | Compound (1-90) | 5.3 | 5.8 | 300.0 | 5.2 | 103.3 |
| Example (91) | Compound (1-91) | 5.8 | 8.1 | 300.0 | 3.7 | 91.0 |
| Example (92) | Compound (1-92) | 5.6 | 9.0 | 300.0 | 3.3 | 109.1 |
| Example (93) | Compound (1-93) | 5.3 | 5.5 | 300.0 | 5.4 | 119.6 |
| Example (94) | Compound (1-94) | 5.8 | 7.5 | 300.0 | 4.0 | 95.4 |
| Example (95) | Compound (1-95) | 5.5 | 7.2 | 300.0 | 4.2 | 90.2 |
| Example (96) | Compound (1-96) | 5.8 | 8.5 | 300.0 | 3.5 | 96.5 |
| Example (97) | Compound (1-97) | 5.2 | 5.4 | 300.0 | 5.5 | 103.3 |
| Example (98) | Compound (1-98) | 5.5 | 5.8 | 300.0 | 5.1 | 96.5 |
| Example (99) | Compound (1-99) | 5.8 | 5.7 | 300.0 | 5.2 | 115.7 |
| Example (100) | Compound (1-100) | 5.1 | 9.1 | 300.0 | 3.3 | 109.7 |
| Example (101) | Compound (1-101) | 5.4 | 9.7 | 300.0 | 3.1 | 117.8 |
| Example (102) | Compound (1-102) | 5.5 | 8.7 | 300.0 | 3.4 | 97.0 |
| Example (103) | Compound (1-103) | 5.5 | 7.1 | 300.0 | 4.2 | 124.3 |
| Example (104) | Compound (1-104) | 5.3 | 9.9 | 300.0 | 3.0 | 119.0 |
| Example 105 | Compound (1-105) | 5.3 | 5.5 | 300.0 | 5.5 | 91.2 |
| Example 106 | Compound (1-106) | 5.3 | 7.4 | 300.0 | 4.0 | 96.9 |
| Example 107 | Compound (1-107) | 5.1 | 5.8 | 300.0 | 5.1 | 91.3 |
| Example 108 | Compound (1-108) | 5.0 | 5.6 | 300.0 | 5.3 | 111.6 |
| Example 109 | Compound (1-109) | 5.4 | 7.7 | 300.0 | 3.9 | 98.8 |
| Example (110) | Compound (1-110) | 5.3 | 9.2 | 300.0 | 3.2 | 114.4 |
| Example (111) | Compound (1-111) | 5.3 | 9.1 | 300.0 | 3.3 | 92.5 |
| Example (112) | Compound (1-112) | 5.1 | 5.6 | 300.0 | 5.3 | 95.0 |
| Example (113) | Compound (1-113) | 5.2 | 8.8 | 300.0 | 3.4 | 128.2 |
| Example 114 | Compound (1-114) | 5.3 | 8.0 | 300.0 | 3.7 | 127.9 |
| Example 115 | Compound (1-115) | 5.3 | 7.0 | 300.0 | 4.3 | 122.0 |
| Example 116 | Compound (1-116) | 5.2 | 8.0 | 300.0 | 3.7 | 112.8 |
| Example 117 | Compound (1-117) | 5.4 | 6.3 | 300.0 | 4.8 | 130.0 |
| Example 118 | Compound (1-118) | 5.4 | 7.8 | 300.0 | 3.9 | 112.6 |
| Example (119) | Compound (1-119) | 5.4 | 9.8 | 300.0 | 3.0 | 91.1 |
| Example 120 | Compound (1-120) | 5.3 | 9.2 | 300.0 | 3.3 | 97.5 |
| Example (121) | Compound (1-121) | 5.2 | 5.3 | 300.0 | 5.6 | 99.2 |
| Example (122) | Compound (1-122) | 5.2 | 5.5 | 300.0 | 5.4 | 124.6 |
| Example (123) | Compound (1-123) | 5.3 | 5.7 | 300.0 | 5.3 | 110.3 |
| Example 124 | Compound (1-124) | 5.5 | 6.1 | 300.0 | 4.9 | 129.0 |
| Example (125) | Compound (1-125) | 5.8 | 6.2 | 300.0 | 4.8 | 115.2 |
| Example 126 | Compound (1-126) | 5.3 | 6.1 | 300.0 | 4.9 | 99.6 |
| Example (127) | Compound (1-127) | 5.4 | 6.5 | 300.0 | 4.6 | 124.7 |
| Example 128 | Compound (1-128) | 5.1 | 6.5 | 300.0 | 4.6 | 104.3 |
| Example (129) | Compound (1-129) | 5.7 | 5.3 | 300.0 | 5.6 | 118.2 |
| Example 130 | Compound (1-130) | 5.1 | 6.9 | 300.0 | 4.4 | 104.7 |
| Example 131 | Compound (1-131) | 5.2 | 7.0 | 300.0 | 4.3 | 124.2 |
| Example 132 | Compound (1-132) | 5.1 | 8.3 | 300.0 | 3.6 | 103.1 |
| Example (133) | Compound (1-133) | 5.8 | 9.6 | 300.0 | 3.1 | 122.8 |
| Example 134 | Compound (1-134) | 5.2 | 5.7 | 300.0 | 5.3 | 123.6 |
| Example (135) | Compound (1-135) | 5.5 | 5.3 | 300.0 | 5.7 | 117.5 |
| Example 136 | Compound (1-136) | 5.1 | 8.2 | 300.0 | 3.6 | 109.7 |
| Example (137) | Compound (1-137) | 5.6 | 6.9 | 300.0 | 4.4 | 108.4 |
| Example (138) | Compound (1-138) | 5.2 | 6.3 | 300.0 | 4.8 | 123.5 |
| Example (139) | Compound (1-139) | 5.6 | 9.2 | 300.0 | 3.2 | 91.5 |
| Example 140 | Compound (1-140) | 5.8 | 7.3 | 300.0 | 4.1 | 123.8 |
| Example 141 | Compound (1-141) | 5.9 | 8.1 | 300.0 | 3.7 | 123.3 |
| Example 142 | Compound (1-142) | 5.2 | 8.5 | 300.0 | 3.5 | 111.7 |
| Example 143 | Compound (1-143) | 5.4 | 6.1 | 300.0 | 4.9 | 93.5 |
| Example 144 | Compound (1-144) | 5.0 | 5.8 | 300.0 | 5.2 | 111.7 |
| Example 145 | Compound (1-145) | 5.8 | 5.9 | 300.0 | 5.1 | 113.6 |
| Example (146) | Compound (1-146) | 5.5 | 5.9 | 300.0 | 5.1 | 97.4 |
| Example (147) | Compound (1-147) | 5.6 | 6.2 | 300.0 | 4.8 | 112.4 |
| Example (148) | Compound (1-148) | 5.8 | 9.4 | 300.0 | 3.2 | 90.0 |
| Example 149 | Compound (1-149) | 5.1 | 6.2 | 300.0 | 4.9 | 99.7 |
| Example (150) | Compound (1-150) | 5.8 | 5.4 | 300.0 | 5.5 | 96.8 |
| Example 151 | Compound (3-1) | 5.0 | 6.6 | 300.0 | 4.5 | 100.1 |
| Example 152 | Compound (3-2) | 5.4 | 9.6 | 300.0 | 3.1 | 116.4 |
| Example 153 | Compound (3-4) | 5.6 | 5.8 | 300.0 | 5.2 | 118.2 |
| Example 154 | Compound (3-4) | 5.1 | 9.1 | 300.0 | 3.3 | 94.5 |
| Example (155) | Compound (3-9) | 5.3 | 5.7 | 300.0 | 5.3 | 97.2 |
| Example 156 | Compound (3-10) | 5.5 | 9.0 | 300.0 | 3.3 | 94.7 |
| Example (157) | Compound (3-11) | 5.4 | 8.2 | 300.0 | 3.7 | 102.4 |
| Example 158 | Compound (3-13) | 5.0 | 8.7 | 300.0 | 3.4 | 94.4 |
| Example 159 | Compound (3-14) | 5.4 | 7.3 | 300.0 | 4.1 | 91.3 |
| Example 160 | Compound (3-15) | 4.9 | 7.7 | 300.0 | 3.9 | 100.0 |
| Example 161 | Compound (3-16) | 5.6 | 9.4 | 300.0 | 3.2 | 117.1 |
| Example 162 | Compound (3-20) | 5.3 | 6.6 | 300.0 | 4.6 | 117.6 |
| Example 163 | Compound (3-21) | 5.1 | 6.2 | 300.0 | 4.8 | 90.1 |
| Example 164 | Compound (3-23) | 5.1 | 7.5 | 300.0 | 4.0 | 110.7 |
| Example (165) | Compound (3-24) | 5.3 | 9.6 | 300.0 | 3.1 | 100.2 |
| Example 166 | Compound (3-25) | 5.1 | 9.4 | 300.0 | 3.2 | 95.1 |
| Example 167 | Compound (3-26) | 5.1 | 6.6 | 300.0 | 4.5 | 114.6 |
| Example 168 | Compound (3-29) | 4.9 | 5.9 | 300.0 | 5.1 | 115.6 |
| Example (169) | Compound (3-30) | 5.4 | 7.3 | 300.0 | 4.1 | 104.7 |
| Example 170 | Compound (3-31) | 5.5 | 9.1 | 300.0 | 3.3 | 110.9 |
| Example 171 | Compound (3-34) | 5.0 | 9.4 | 300.0 | 3.2 | 103.8 |
| Example 172 | Compound (3-35) | 5.1 | 6.9 | 300.0 | 4.4 | 110.2 |
| Example (173) | Compound (3-49) | 5.5 | 6.6 | 300.0 | 4.6 | 103.3 |
| Example 174 | Compound (3-50) | 4.9 | 9.0 | 300.0 | 3.3 | 115.1 |
| Example (175) | Compound (3-58) | 5.6 | 6.0 | 300.0 | 5.0 | 93.2 |
| Example (176) | Compound (3-60) | 5.0 | 6.2 | 300.0 | 4.9 | 118.4 |
| Example (177) | Compound (3-61) | 5.5 | 7.6 | 300.0 | 3.9 | 92.6 |
| Example 178 | Compound (3-66) | 5.5 | 7.3 | 300.0 | 4.1 | 105.5 |
| Example (179) | Compound (3-68) | 5.4 | 8.0 | 300.0 | 3.7 | 99.1 |
| Example 180 | Compound (3-69) | 5.4 | 7.5 | 300.0 | 4.0 | 91.9 |
| Example (181) | Compound (3-70) | 5.3 | 6.8 | 300.0 | 4.4 | 92.5 |
| Example 182 | Compound (3-71) | 5.1 | 6.7 | 300.0 | 4.5 | 104.8 |
| Example (183) | Compound (3-72) | 5.1 | 6.3 | 300.0 | 4.8 | 111.4 |
| Example 184 | Compound (4-4) | 4.9 | 6.7 | 300.0 | 4.5 | 94.2 |
| Example (185) | Compound (4-7) | 5.2 | 8.0 | 300.0 | 3.8 | 102.0 |
| Example (186) | Compound (4-8) | 4.9 | 7.3 | 300.0 | 4.1 | 105.4 |
| Example (187) | Compound (4-9) | 4.7 | 7.0 | 300.0 | 4.3 | 105.3 |
| Example (188) | Compound (4-10) | 4.6 | 6.7 | 300.0 | 4.5 | 94.0 |
| Example (189) | Compound (4-11) | 5.2 | 9.2 | 300.0 | 3.2 | 93.4 |
| Example 190 | Compound (4-24) | 4.8 | 6.3 | 300.0 | 4.7 | 99.9 |
| Example (191) | Compound (4-25) | 5.0 | 8.9 | 300.0 | 3.4 | 98.4 |
| Example (192) | Compound (4-27) | 5.0 | 6.6 | 300.0 | 4.5 | 99.4 |
| Example (193) | Compound (4-32) | 5.0 | 5.8 | 300.0 | 5.2 | 91.4 |
| Example 194 | Compound (4-33) | 4.6 | 6.0 | 300.0 | 5.0 | 95.3 |
| Example (195) | Compound (4-36) | 4.6 | 6.1 | 300.0 | 4.9 | 105.1 |
| Example (196) | Compound (4-43) | 4.8 | 5.8 | 300.0 | 5.2 | 96.0 |
| Example (197) | Compound (4-44) | 4.5 | 6.3 | 300.0 | 4.8 | 90.2 |
| Example (198) | Compound (4-45) | 4.3 | 6.5 | 300.0 | 4.6 | 103.4 |
| Example (199) | Compound (4-47) | 5.1 | 7.0 | 300.0 | 4.3 | 92.5 |
| Example (200) | Compound (4-48) | 4.9 | 6.7 | 300.0 | 4.5 | 96.4 |
| Example 201 | Compound (4-55) | 5.1 | 6.9 | 300.0 | 4.3 | 98.5 |
| Example 202 | Compound (4-58) | 4.8 | 6.2 | 300.0 | 4.8 | 105.0 |
| Example (203) | Compound (4-61) | 4.9 | 7.7 | 300.0 | 3.9 | 105.8 |
| Example 204 | Compound (4-62) | 5.0 | 8.8 | 300.0 | 3.4 | 102.7 |
| Example (205) | Compound (4-63) | 4.9 | 7.5 | 300.0 | 4.0 | 97.3 |
| Example 206 | Compound (4-64) | 5.2 | 6.7 | 300.0 | 4.5 | 108.4 |
| Example (207) | Compound (4-65) | 4.9 | 5.7 | 300.0 | 5.3 | 100.4 |
| Example 208 | Compound (4-66) | 5.1 | 7.0 | 300.0 | 4.3 | 105.8 |
| Example (209) | Compound (4-67) | 5.3 | 7.7 | 300.0 | 3.9 | 101.3 |
| Example 210 | Compound (4-68) | 4.9 | 6.4 | 300.0 | 4.7 | 102.2 |
| Example 211 | Compound (4-69) | 4.8 | 8.2 | 300.0 | 3.6 | 93.2 |
| Example 212 | Compound (4-70) | 5.2 | 6.2 | 300.0 | 4.8 | 106.1 |
| Example (213) | Compound (4-71) | 4.8 | 8.8 | 300.0 | 3.4 | 95.2 |
| Example 214 | Compound (4-104) | 5.3 | 7.6 | 300.0 | 3.9 | 108.3 |
| Example 215 | Compound (4-105) | 5.1 | 7.9 | 300.0 | 3.8 | 103.7 |
| Example 216 | Compound (4-106) | 5.0 | 8.5 | 300.0 | 3.5 | 108.6 |
| Example 217 | Compound (4-107) | 5.1 | 6.7 | 300.0 | 4.4 | 103.3 |
| Example 218 | Compound (4-108) | 5.2 | 9.7 | 300.0 | 3.1 | 92.2 |
| Example 219 | Compound (5-2) | 5.3 | 8.7 | 300.0 | 3.5 | 90.8 |
| Example 220 | Compound (5-4) | 5.3 | 5.8 | 300.0 | 5.2 | 101.7 |
| Example 221 | Compound (5-6) | 5.3 | 9.5 | 300.0 | 3.2 | 98.9 |
| Example 222 | Compound (5-7) | 5.4 | 5.7 | 300.0 | 5.3 | 93.0 |
| Example 223 | Compound (5-10) | 5.5 | 6.1 | 300.0 | 4.9 | 106.5 |
| Example 224 | Compound (5-11) | 5.4 | 8.9 | 300.0 | 3.4 | 92.8 |
| Example (225) | Compound (5-12) | 5.3 | 6.7 | 300.0 | 4.5 | 97.9 |
| Example (226) | Compound (5-16) | 5.1 | 6.9 | 300.0 | 4.3 | 101.9 |
| Example (227) | Compound (5-17) | 5.0 | 8.3 | 300.0 | 3.6 | 103.7 |
| Example (228) | Compound (5-18) | 5.2 | 7.6 | 300.0 | 4.0 | 104.7 |
| Example (229) | Compound (5-19) | 4.8 | 5.9 | 300.0 | 5.1 | 96.9 |
| Example 230 | Compound (5-20) | 4.7 | 6.6 | 300.0 | 4.6 | 98.1 |
| Example 231 | Compound (5-21) | 4.8 | 6.5 | 300.0 | 4.6 | 102.4 |
| Example 232 | Compound (5-22) | 5.0 | 6.2 | 300.0 | 4.9 | 103.7 |
| Example (233) | Compound (5-23) | 5.2 | 7.2 | 300.0 | 4.2 | 109.3 |
| Example 234 | Compound (5-24) | 4.9 | 5.9 | 300.0 | 5.0 | 96.7 |
| Example (235) | Compound (5-27) | 5.5 | 9.0 | 300.0 | 3.3 | 91.3 |
| Example 236 | Compound (5-28) | 5.6 | 9.0 | 300.0 | 3.3 | 92.3 |
| Example (237) | Compound (5-30) | 5.4 | 5.8 | 300.0 | 5.2 | 98.6 |
| Example (238) | Compound (5-32) | 5.5 | 7.6 | 300.0 | 4.0 | 98.2 |
| Example (239) | Compound (5-33) | 5.4 | 8.1 | 300.0 | 3.7 | 104.1 |
| Example (240) | Compound (5-34) | 4.9 | 6.1 | 300.0 | 4.9 | 105.0 |
| Example 241 | Compound (5-36) | 5.4 | 7.0 | 300.0 | 4.3 | 102.2 |
| Example 242 | Compound (5-37) | 5.1 | 6.0 | 300.0 | 5.0 | 96.6 |
| Example (243) | Compound (5-38) | 4.9 | 7.6 | 300.0 | 4.0 | 90.6 |
| Example (244) | Compound (5-40) | 5.4 | 6.4 | 300.0 | 4.7 | 105.2 |
| Example (245) | Compound (5-41) | 4.9 | 6.7 | 300.0 | 4.5 | 93.9 |
| Example 246 | Compound (5-42) | 5.4 | 7.4 | 300.0 | 4.1 | 101.1 |
| Example (247) | Compound (5-43) | 5.5 | 8.0 | 300.0 | 3.7 | 102.9 |
| Example 248 | Compound (5-44) | 5.6 | 5.7 | 300.0 | 5.3 | 94.0 |
| Example (249) | Compound (5-45) | 4.8 | 9.4 | 300.0 | 3.2 | 99.3 |
| Example 250 | Compound (5-47) | 5.3 | 8.3 | 300.0 | 3.6 | 109.2 |
| Example 251 | Compound (5-49) | 5.2 | 6.5 | 300.0 | 4.6 | 103.3 |
| Example 252 | Compound (5-50) | 5.0 | 6.2 | 300.0 | 4.8 | 106.2 |
| Example (253) | Compound (5-51) | 5.3 | 6.2 | 300.0 | 4.8 | 98.8 |
| Example (254) | Compound (6-10) | 5.4 | 9.6 | 300.0 | 3.1 | 91.4 |
| Example (255) | Compound (6-11) | 5.2 | 7.4 | 300.0 | 4.1 | 104.4 |
| Example (256) | Compound (6-12) | 5.3 | 6.2 | 300.0 | 4.8 | 90.2 |
| Example (257) | Compound (6-13) | 5.7 | 6.8 | 300.0 | 4.4 | 105.9 |
| Example (258) | Compound (6-14) | 5.4 | 6.3 | 300.0 | 4.8 | 103.5 |
| Example (259) | Compound (6-15) | 5.4 | 6.5 | 300.0 | 4.6 | 111.5 |
| Example 260 | Compound (6-16) | 5.2 | 6.7 | 300.0 | 4.4 | 109.9 |
| Example (261) | Compound (6-17) | 5.4 | 9.4 | 300.0 | 3.2 | 101.4 |
| Example 262 | Compound (6-18) | 5.5 | 5.7 | 300.0 | 5.3 | 110.0 |
| Example (263) | Compound (6-19) | 5.5 | 6.1 | 300.0 | 4.9 | 111.3 |
| Example 264 | Compound (6-20) | 5.3 | 9.2 | 300.0 | 3.3 | 110.0 |
| Example 265 | Compound (6-21) | 5.2 | 7.2 | 300.0 | 4.2 | 98.8 |
| Example (266) | Compound (6-22) | 5.7 | 6.3 | 300.0 | 4.7 | 97.0 |
| Example (267) | Compound (6-23) | 5.6 | 6.8 | 300.0 | 4.4 | 96.2 |
| Example 268 | Compound (6-24) | 5.6 | 6.6 | 300.0 | 4.6 | 90.9 |
| Example (269) | Compound (6-28) | 5.6 | 7.1 | 300.0 | 4.2 | 116.5 |
| Example 270 | Compound (6-32) | 5.8 | 9.9 | 300.0 | 3.0 | 90.2 |
| Example (271) | Compound (6-33) | 5.4 | 6.4 | 300.0 | 4.7 | 99.7 |
| Example 272 | Compound (6-39) | 5.3 | 7.0 | 300.0 | 4.3 | 95.8 |
| Example (273) | Compound (6-40) | 5.6 | 7.3 | 300.0 | 4.1 | 111.7 |
| Example (274) | Compound (6-41) | 5.7 | 8.5 | 300.0 | 3.5 | 96.2 |
| Example (275) | Compound (6-43) | 5.6 | 6.7 | 300.0 | 4.5 | 92.2 |
| Example (276) | Compound (6-47) | 5.5 | 5.7 | 300.0 | 5.3 | 95.6 |
| Example (277) | Compound (6-49) | 5.5 | 6.8 | 300.0 | 4.4 | 119.5 |
| Example (278) | Compound (6-50) | 5.2 | 7.1 | 300.0 | 4.2 | 101.8 |
| Example (279) | Compound (7-9) | 5.7 | 9.1 | 300.0 | 3.3 | 114.6 |
| Example 280 | Compound (7-10) | 5.8 | 10.0 | 300.0 | 3.0 | 110.4 |
| Example (281) | Compound (7-11) | 5.6 | 6.7 | 300.0 | 4.5 | 100.4 |
| Example (282) | Compound (7-12) | 5.6 | 6.0 | 300.0 | 5.0 | 94.9 |
| Example (283) | Compound (7-14) | 5.8 | 6.8 | 300.0 | 4.4 | 94.9 |
| Example (284) | Compound (7-16) | 5.5 | 7.4 | 300.0 | 4.1 | 94.1 |
| Example (285) | Compound (7-17) | 5.7 | 9.4 | 300.0 | 3.2 | 91.5 |
| Example (286) | Compound (7-19) | 5.7 | 6.0 | 300.0 | 5.0 | 105.0 |
| Example (287) | Compound (7-20) | 5.5 | 9.9 | 300.0 | 3.0 | 104.1 |
| Example (288) | Compound (7-21) | 5.9 | 7.4 | 300.0 | 4.0 | 104.4 |
| Example (289) | Compound (7-22) | 5.6 | 8.0 | 300.0 | 3.8 | 118.1 |
| Example 290 | Compound (7-25) | 5.8 | 9.6 | 300.0 | 3.1 | 108.0 |
| Example 291 | Compound (7-26) | 5.8 | 6.7 | 300.0 | 4.5 | 98.5 |
| Example 292 | Compound (7-27) | 5.7 | 7.8 | 300.0 | 3.8 | 111.9 |
| Example 293 | Compound (7-30) | 5.6 | 6.4 | 300.0 | 4.7 | 92.4 |
| Example (294) | Compound (7-31) | 5.8 | 5.7 | 300.0 | 5.3 | 114.6 |
| Example (295) | Compound (7-36) | 5.8 | 8.9 | 300.0 | 3.4 | 113.0 |
| Example (296) | Compound (7-46) | 5.5 | 8.5 | 300.0 | 3.5 | 116.9 |
| Example (297) | Compound (7-50) | 5.8 | 6.4 | 300.0 | 4.7 | 103.7 |
| Example (298) | Compound (7-51) | 5.8 | 6.2 | 300.0 | 4.8 | 112.2 |
| Example (299) | Compound (7-52) | 5.6 | 8.3 | 300.0 | 3.6 | 94.2 |
| Example 300 | Compound (7-56) | 5.6 | 7.8 | 300.0 | 3.8 | 94.0 |
| Example 301 | Compound (7-61) | 5.6 | 8.8 | 300.0 | 3.4 | 94.3 |
| Example 302 | Compound (7-62) | 5.9 | 6.6 | 300.0 | 4.5 | 103.1 |
| Example 303 | Compound (7-63) | 5.6 | 8.3 | 300.0 | 3.6 | 108.8 |
| Example 304 | Compound (8-1) | 5.2 | 9.5 | 300.0 | 3.2 | 98.5 |
| Example 305 | Compound (8-2) | 5.5 | 6.2 | 300.0 | 4.9 | 110.8 |
| Example 306 | Compound (8-5) | 5.6 | 7.8 | 300.0 | 3.8 | 103.2 |
| Example 307 | Compound (8-6) | 5.4 | 7.2 | 300.0 | 4.2 | 90.7 |
| Example 308 | Compound (8-7) | 5.4 | 7.3 | 300.0 | 4.1 | 103.1 |
| Example 309 | Compound (8-9) | 5.6 | 7.3 | 300.0 | 4.1 | 119.3 |
| Example 310 | Compound (8-10) | 5.3 | 5.9 | 300.0 | 5.1 | 107.6 |
| Example 311 | Compound (8-11) | 5.6 | 5.8 | 300.0 | 5.1 | 95.9 |
| Example 312 | Compound (8-12) | 5.3 | 6.4 | 300.0 | 4.7 | 109.5 |
| Example 313 | Compound (8-16) | 5.2 | 10.0 | 300.0 | 3.0 | 118.9 |
| Example 314 | Compound (8-17) | 5.7 | 8.2 | 300.0 | 3.6 | 118.3 |
| Example 315 | Compound (8-18) | 5.3 | 9.4 | 300.0 | 3.2 | 99.1 |
| Example 316 | Compound (8-20) | 5.2 | 9.8 | 300.0 | 3.1 | 115.4 |
| Example (317) | Compound (8-22) | 5.6 | 7.3 | 300.0 | 4.1 | 103.3 |
| Example 318 | Compound (8-25) | 5.8 | 8.2 | 300.0 | 3.6 | 100.3 |
| Example (319) | Compound (8-26) | 5.6 | 7.0 | 300.0 | 4.3 | 115.9 |
| Example 320 | Compound (8-27) | 5.8 | 7.1 | 300.0 | 4.2 | 108.4 |
| Example 321 | Compound (8-30) | 5.3 | 6.3 | 300.0 | 4.8 | 101.6 |
| Example 322 | Compound (8-31) | 5.6 | 9.9 | 300.0 | 3.0 | 114.0 |
| Example 323 | Compound (8-35) | 5.7 | 6.7 | 300.0 | 4.5 | 106.4 |
| Example 324 | Compound (8-40) | 5.2 | 9.8 | 300.0 | 3.1 | 118.0 |
| Example 325 | Compound (8-47) | 5.4 | 5.7 | 300.0 | 5.2 | 97.0 |
| Example 326 | Compound (8-49) | 5.4 | 5.9 | 300.0 | 5.1 | 104.3 |
| Example 327 | Compound (8-50) | 5.4 | 9.9 | 300.0 | 3.0 | 112.9 |
| Example 328 | Compound (8-51) | 5.3 | 7.0 | 300.0 | 4.3 | 109.0 |
| Example (329) | Compound (8-55) | 5.2 | 7.9 | 300.0 | 3.8 | 90.5 |
| Example 330 | Compound (8-57) | 5.2 | 8.6 | 300.0 | 3.5 | 112.6 |
| Example (331) | Compound (8-58) | 5.7 | 9.8 | 300.0 | 3.1 | 109.1 |
| Example 332 | Compound (8-59) | 5.5 | 7.2 | 300.0 | 4.1 | 101.5 |
| Example (333) | Compound (8-60) | 5.4 | 6.4 | 300.0 | 4.7 | 99.1 |
| Example 334 | Compound (8-61) | 5.6 | 6.9 | 300.0 | 4.4 | 118.6 |
| Example (335) | Compound (9-2) | 5.6 | 6.1 | 300.0 | 4.9 | 98.5 |
| Example 336 | Compound (9-8) | 5.4 | 5.8 | 300.0 | 5.1 | 116.6 |
| Example (337) | Compound (9-11) | 5.5 | 9.4 | 300.0 | 3.2 | 113.9 |
| Example 338 | Compound (9-12) | 5.8 | 6.5 | 300.0 | 4.6 | 95.5 |
| Example (339) | Compound (9-13) | 5.8 | 6.7 | 300.0 | 4.5 | 115.5 |
| Example 340 | Compound (9-14) | 5.5 | 9.2 | 300.0 | 3.3 | 106.5 |
| Example 341 | Compound (9-15) | 5.3 | 6.7 | 300.0 | 4.5 | 116.2 |
| Example 342 | Compound (9-17) | 5.5 | 6.2 | 300.0 | 4.9 | 95.4 |
| Example (343) | Compound (9-18) | 5.8 | 6.0 | 300.0 | 5.0 | 102.5 |
| Example 344 | Compound (9-19) | 5.3 | 5.7 | 300.0 | 5.3 | 118.7 |
| Example 345 | Compound (9-20) | 5.5 | 7.7 | 300.0 | 3.9 | 102.6 |
| Example 346 | Compound (9-21) | 5.3 | 6.8 | 300.0 | 4.4 | 102.3 |
| Example 347 | Compound (9-22) | 5.3 | 8.0 | 300.0 | 3.7 | 91.2 |
| Example 348 | Compound (9-25) | 5.8 | 6.6 | 300.0 | 4.6 | 106.8 |
| Example (349) | Compound (9-27) | 5.7 | 6.6 | 300.0 | 4.6 | 116.0 |
| Example 350 | Compound (9-28) | 5.4 | 5.9 | 300.0 | 5.1 | 94.8 |
| Example (351) | Compound (9-29) | 5.8 | 8.7 | 300.0 | 3.4 | 93.2 |
| Example 352 | Compound (9-30) | 5.3 | 9.9 | 300.0 | 3.0 | 103.9 |
| Example (353) | Compound (9-36) | 5.4 | 9.6 | 300.0 | 3.1 | 108.1 |
| Example 354 | Compound (9-37) | 5.2 | 6.3 | 300.0 | 4.8 | 102.0 |
| Example (355) | Compound (9-38) | 5.4 | 9.1 | 300.0 | 3.3 | 109.1 |
| Example 356 | Compound (9-46) | 5.5 | 6.0 | 300.0 | 5.0 | 92.8 |
| Example (357) | Compound (9-47) | 5.7 | 9.4 | 300.0 | 3.2 | 103.0 |
| Example (358) | Compound (9-49) | 5.5 | 9.4 | 300.0 | 3.2 | 93.4 |
| Example (359) | Compound (9-50) | 5.5 | 6.5 | 300.0 | 4.6 | 98.8 |
| Example 360 | Compound (9-51) | 5.8 | 6.7 | 300.0 | 4.5 | 101.6 |
| Example 361 | Compound (9-53) | 5.2 | 6.6 | 300.0 | 4.5 | 91.6 |
| Example 362 | Compound (9-54) | 5.4 | 6.5 | 300.0 | 4.6 | 109.9 |
| Example 363 | Compound (9-57) | 5.8 | 8.1 | 300.0 | 3.7 | 108.3 |
| Example (364) | Compound (9-58) | 5.4 | 8.6 | 300.0 | 3.5 | 99.3 |
| Example 365 | Compound (10-1) | 5.6 | 6.2 | 300.0 | 4.9 | 100.4 |
| Example (366) | Compound (10-2) | 5.9 | 6.2 | 300.0 | 4.9 | 116.7 |
| Example (367) | Compound (10-4) | 5.7 | 6.2 | 300.0 | 4.8 | 110.5 |
| Example (368) | Compound (10-6) | 5.8 | 7.6 | 300.0 | 4.0 | 113.3 |
| Example (369) | Compound (10-7) | 5.6 | 6.2 | 300.0 | 4.8 | 109.6 |
| Example 370 | Compound (10-8) | 5.7 | 9.4 | 300.0 | 3.2 | 111.8 |
| Example (371) | Compound (10-10) | 5.7 | 6.2 | 300.0 | 4.8 | 97.9 |
| Example 372 | Compound (10-11) | 5.8 | 6.3 | 300.0 | 4.8 | 105.9 |
| Example (373) | Compound (10-12) | 5.5 | 8.1 | 300.0 | 3.7 | 111.5 |
| Example 374 | Compound (10-14) | 5.9 | 5.8 | 300.0 | 5.2 | 94.4 |
| Example (375) | Compound (10-15) | 5.7 | 7.2 | 300.0 | 4.2 | 105.9 |
| Example (376) | Compound (10-16) | 5.8 | 9.0 | 300.0 | 3.3 | 94.0 |
| Example (377) | Compound (10-17) | 5.7 | 7.1 | 300.0 | 4.3 | 116.7 |
| Example (378) | Compound (10-18) | 5.6 | 7.0 | 300.0 | 4.3 | 110.8 |
| Example (379) | Compound (10-19) | 5.7 | 5.9 | 301.0 | 5.1 | 109.0 |
| Example 380 | Compound (10-20) | 5.8 | 7.1 | 302.0 | 4.2 | 90.3 |
| Example 381 | Compound (10-21) | 5.8 | 7.3 | 303.0 | 4.2 | 97.2 |
| Example 382 | Compound (10-22) | 5.6 | 8.8 | 304.0 | 3.5 | 95.4 |
| Example (383) | Compound (10-23) | 5.8 | 8.7 | 305.0 | 3.5 | 93.2 |
| Example (384) | Compound (10-24) | 5.8 | 6.2 | 306.0 | 4.9 | 108.5 |
| Example (385) | Compound (10-45) | 5.7 | 9.4 | 307.0 | 3.3 | 107.9 |
| Example (386) | Compound (10-46) | 5.6 | 6.9 | 308.0 | 4.4 | 119.1 |
| Example (387) | Compound (10-47) | 5.6 | 7.5 | 309.0 | 4.1 | 118.6 |
| Example (388) | Compound (10-48) | 5.8 | 8.1 | 310.0 | 3.8 | 97.6 |
| Example (389) | Compound (10-49) | 5.8 | 10.1 | 311.0 | 3.1 | 92.2 |
| Example 390 | Compound (10-50) | 5.7 | 6.1 | 312.0 | 5.1 | 118.8 |
상기 표 5에서 볼 수 있는 것처럼, 화학식 1, 화학식2의 화합물들을 정공 수송층으로 사용해 본 결과 구동전압 측면에서는 화학식 2의 화합물들(Ar3가 
인 경우)이 낮은 구동전압을 나타냈으며, 화합물 1-5, 화합물 1-6도 비교적 낮은 구동전압을 나타내는 것을 확인하였다. As can be seen in Table 5 above, as a result of using the compounds of Formula 1 and Formula 2 as the hole transport layer, the compounds of Formula 2 (Ar 3 is In the case of), a low driving voltage was shown, and it was confirmed that Compounds 1-5 and 1-6 also exhibit relatively low driving voltages.
특히 인돌 화합물의 경우 화학식 2의 화합물들보다 비교적 높은 효율 및 수명을 나타내는 것을 확인하였다. In particular, it was confirmed that the indole compound exhibits relatively higher efficiency and lifespan than the compounds of Formula 2.
이에 낮은 구동전압을 나타내는 화합물 4-45와 효율 및 수명이 좋은 인돌 화합물들을 각각 정공 수송층과 발광보조층으로 사용하여 하기와 같이 유기전기발광소자를 제작하였다. Accordingly, the organic electroluminescent device was manufactured by using the compound 4-45 showing the low driving voltage and the indole compound having good efficiency and lifetime as the hole transporting layer and the light emitting auxiliary layer, respectively.
[실시예 7] Example 7
발광 radiation
보조층Secondary layer
유리 기판에 형성된 ITO층(양극) 상에 2-TNATA를 진공증착하여 60 nm 두께의 정공주입층을 형성한 후, 정공주입층 위에 정공수송 화합물로서 화합물 4-45를 20 nm 두께로 진공증착하여 정공 수송층을 형성하였다. 다음으로 정공 수송층 위에 발광 보조층 재료로서 본 발명에 따른 화합물 및 비교 화합물을 20 nm의 두께로 진공증착하여 발광 보조층을 형성하였다. 발광 보조층을 형성한 후, 상부에 호스트 물질로 CBP[4,4'-N,N'-dicarbazole-biphenyl]를 도판트 물질로 (piq)2Ir(acac) [bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate]를 95:5 중량비로 도핑하여 30nm 두께로 발광층을 증착하였다. 이어서 홀저지층으로 (1,1’-비스페닐)-4-올레이토)비스(2-메틸-8-퀴놀린올레이토)알루미늄(이하 BAlq로 약기함)을 10 nm 두께로 진공증착하고, 전자수송층으로 트리스(8-퀴놀리놀)알루미늄(이하 Alq3로 약칭함)을 40 nm 두께로 성막하였다. 이후, 전자주입층으로 할로젠화 알칼리 금속인 LiF를 0.2 nm 두께로 증착하고, 이어서 Al을 150 nm의 두께로 증착하여 음극으로 사용함으로서 유기전계 발광소자를 제조하였다.2-TNATA was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to form a hole injection layer having a thickness of 60 nm, and then compound 4-45 was vacuum-deposited to a thickness of 20 nm as a hole transport compound on the hole injection layer. A hole transport layer was formed. Next, the compound according to the present invention and the comparative compound were vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emission auxiliary layer. After the emission auxiliary layer was formed, CBP [4,4'-N, N'-dicarbazole-biphenyl] was used as a dopant material as a host material (piq) 2 Ir (acac) [bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate] was doped in a weight ratio of 95: 5 to deposit a light emitting layer with a thickness of 30 nm. Subsequently, (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm with a holding layer. Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was formed into a transport layer to a thickness of 40 nm. Thereafter, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm as an electron injection layer, and then, Al was deposited to a thickness of 150 nm to use an organic light emitting device.
[[
비교예Comparative example
2] 2]
상기 실시예 7과 동일하게 유기전계 발광소자를 제작하되, 본 발명의 화합물 대신 하기 비교 화합물 2을 이용하여 발광보조층을 형성하였다.An organic light emitting diode was manufactured in the same manner as in Example 7, except that the light emitting auxiliary layer was formed using the following Comparative Compound 2 instead of the compound of the present invention.
<비교 화합물 2> <Comparative Compound 2>
[[
비교예Comparative example
3] 3]
상기 실시예 7과 동일하게 유기전계 발광소자를 제작하되, 본 발명의 화합물 대신 하기 비교 화합물 3을 이용하여 발광보조층을 형성하였다.An organic light emitting diode was manufactured in the same manner as in Example 7, except that the light emitting auxiliary layer was formed using the following Comparative Compound 3 instead of the compound of the present invention.
<비교 화합물 3> Comparative Compound 3
[[
비교예Comparative example
4] 4]
상기 실시예 7과 동일하게 유기전계 발광소자를 제작하되, 본 발명의 화합물 대신 하기 비교 화합물 4을 이용하여 발광보조층을 형성하였다.An organic light emitting diode was manufactured in the same manner as in Example 7, except that the light emitting auxiliary layer was formed using the following Comparative Compound 4 instead of the compound of the present invention.
<비교 화합물 4> <Comparative Compound 4>
[[
비교예Comparative example
5] 5]
상기 실시예 7과 동일하게 유기전계 발광소자를 제작하되, 본 발명의 화합물 대신 하기 비교 화합물 5을 이용하여 발광보조층을 형성하였다.An organic light emitting diode was manufactured in the same manner as in Example 7, except that the light emitting auxiliary layer was formed using the following Comparative Compound 5 instead of the compound of the present invention.
<비교 화합물 5> Comparative Compound 5
[[
비교예Comparative example
6] 6]
상기 실시예에서 발광 보조층을 사용하지 않고 정공 수송층으로 화합물 4-45만을 사용하였다. In the above embodiment, only Compound 4-45 was used as the hole transport layer without using the emission auxiliary layer.
이와 같이 제조된 실시예 및 비교예 유기전기발광소자에 순바이어스 직류전압을 가하여 포토리서치(photoresearch)사의 PR-650으로 전기발광(EL) 특성을 측정하였으며, 그 측정 결과 300cd/m2 기준 휘도에서 맥사이언스사에서 제조된 수명 측정 장비를 통해 T90 수명을 측정하였다.The electroluminescent (EL) characteristics of the Example and Comparative Example organic electroluminescent devices manufactured as described above were applied to the PR-650 of photoresearch by applying a forward bias DC voltage, and the measured results were measured at 300 cd / m 2 reference luminance. The T90 life was measured using a life measurement instrument manufactured by McScience.
하기 표 6은 본 발명에 따른 화합물을 적용한 실시예 및 비교예에 대한 소자제작 및 그 평가 결과를 나타낸다.Table 6 below shows device fabrication and evaluation results of Examples and Comparative Examples to which the compound according to the present invention is applied.
표 6
Table 6
| 화합물 | 구동전압 | 전류(mA/cm2) | 휘도(cd/m2) | 효율(cd/A) | T(90) | CIE | ||
| x | y | |||||||
| 비교예(2) | 비교화합물 2 | 5.7 | 7.2 | 300.0 | 4.2 | 99.1 | 0.66 | 0.32 |
| 비교예(3) | 비교화합물 3 | 5.6 | 7.5 | 300.0 | 4.0 | 95.1 | 0.66 | 0.32 |
| 비교예(4) | 비교화합물 4 | 5.7 | 8.5 | 300.0 | 3.5 | 108.7 | 0.66 | 0.32 |
| 비교예(5) | 비교화합물 5 | 5.6 | 8.2 | 300.0 | 3.7 | 91.8 | 0.66 | 0.32 |
| 비교예(6) | 사용하지 않음 | 4.5 | 6.5 | 300 | 4.6 | 91.6 | 0.66 | 0.32 |
| 실시예(1) | 화합물(1-1) | 5.0 | 5.3 | 300.0 | 5.7 | 158.9 | 0.66 | 0.33 |
| 실시예(2) | 화합물(1-2) | 4.9 | 5.3 | 300.0 | 5.7 | 162.6 | 0.66 | 0.32 |
| 실시예(3) | 화합물(1-3) | 4.9 | 5.6 | 300.0 | 5.3 | 122.0 | 0.66 | 0.33 |
| 실시예(4) | 화합물(1-4) | 4.5 | 5.4 | 300.0 | 5.6 | 157.7 | 0.66 | 0.32 |
| 실시예(5) | 화합물(1-5) | 4.3 | 4.4 | 300.0 | 6.8 | 180.9 | 0.66 | 0.32 |
| 실시예(6) | 화합물(1-6) | 4.3 | 4.5 | 300.0 | 6.7 | 191.0 | 0.66 | 0.32 |
| 실시예(7) | 화합물(1-7) | 4.7 | 5.6 | 300.0 | 5.4 | 131.5 | 0.66 | 0.33 |
| 실시예(8) | 화합물(1-8) | 4.8 | 5.3 | 300.0 | 5.7 | 119.8 | 0.66 | 0.32 |
| 실시예(9) | 화합물(1-9) | 5.2 | 5.3 | 300.0 | 5.7 | 147.5 | 0.66 | 0.32 |
| 실시예(10) | 화합물(1-10) | 4.9 | 5.5 | 300.0 | 5.4 | 138.4 | 0.66 | 0.32 |
| 실시예(11) | 화합물(1-11) | 4.8 | 5.5 | 300.0 | 5.5 | 146.1 | 0.66 | 0.32 |
| 실시예(12) | 화합물(1-12) | 4.7 | 5.5 | 300.0 | 5.4 | 140.8 | 0.66 | 0.33 |
| 실시예(13) | 화합물(1-13) | 4.8 | 5.4 | 300.0 | 5.5 | 138.7 | 0.66 | 0.32 |
| 실시예(14) | 화합물(1-14) | 4.4 | 5.4 | 300.0 | 5.6 | 178.9 | 0.66 | 0.33 |
| 실시예(15) | 화합물(1-15) | 5.0 | 5.5 | 300.0 | 5.5 | 116.1 | 0.66 | 0.33 |
| 실시예(16) | 화합물(1-16) | 5.1 | 5.6 | 300.0 | 5.4 | 147.9 | 0.66 | 0.33 |
| 실시예(17) | 화합물(1-17) | 4.8 | 5.5 | 300.0 | 5.4 | 127.1 | 0.66 | 0.32 |
| 실시예(18) | 화합물(1-18) | 4.9 | 5.3 | 300.0 | 5.7 | 121.1 | 0.66 | 0.32 |
| 실시예(19) | 화합물(1-19) | 5.1 | 5.4 | 300.0 | 5.6 | 134.3 | 0.66 | 0.32 |
| 실시예(20) | 화합물(1-20) | 4.9 | 5.4 | 300.0 | 5.6 | 119.7 | 0.66 | 0.33 |
| 실시예(21) | 화합물(1-21) | 5.0 | 5.6 | 300.0 | 5.4 | 140.7 | 0.66 | 0.32 |
| 실시예(22) | 화합물(1-22) | 4.9 | 5.6 | 300.0 | 5.3 | 144.9 | 0.66 | 0.32 |
| 실시예(23) | 화합물(1-23) | 5.2 | 5.7 | 300.0 | 5.3 | 146.8 | 0.66 | 0.32 |
| 실시예(24) | 화합물(1-24) | 5.1 | 5.3 | 300.0 | 5.6 | 129.1 | 0.66 | 0.33 |
| 실시예(25) | 화합물(1-25) | 5.2 | 5.6 | 300.0 | 5.4 | 125.4 | 0.66 | 0.33 |
| 실시예(26) | 화합물(1-26) | 5.2 | 5.4 | 300.0 | 5.6 | 138.2 | 0.66 | 0.33 |
| 실시예(27) | 화합물(1-27) | 5.0 | 5.6 | 300.0 | 5.3 | 142.6 | 0.66 | 0.32 |
| 실시예(28) | 화합물(1-28) | 5.0 | 5.3 | 300.0 | 5.7 | 145.4 | 0.66 | 0.33 |
| 실시예(29) | 화합물(1-29) | 5.0 | 5.5 | 300.0 | 5.4 | 132.4 | 0.66 | 0.33 |
| 실시예(30) | 화합물(1-30) | 4.8 | 5.6 | 300.0 | 5.3 | 131.6 | 0.66 | 0.33 |
| 실시예(31) | 화합물(1-31) | 5.0 | 5.4 | 300.0 | 5.5 | 145.3 | 0.66 | 0.32 |
| 실시예(32) | 화합물(1-32) | 5.1 | 5.4 | 300.0 | 5.6 | 144.8 | 0.66 | 0.32 |
| 실시예(33) | 화합물(1-33) | 5.1 | 5.6 | 300.0 | 5.3 | 125.7 | 0.66 | 0.33 |
| 실시예(34) | 화합물(1-34) | 4.7 | 5.4 | 300.0 | 5.6 | 129.3 | 0.66 | 0.33 |
| 실시예(35) | 화합물(1-35) | 4.7 | 5.6 | 300.0 | 5.3 | 124.4 | 0.66 | 0.32 |
| 실시예(36) | 화합물(1-36) | 4.9 | 5.4 | 300.0 | 5.6 | 143.1 | 0.66 | 0.33 |
| 실시예(37) | 화합물(1-37) | 4.9 | 5.6 | 300.0 | 5.3 | 117.6 | 0.66 | 0.32 |
| 실시예(38) | 화합물(1-38) | 4.9 | 5.5 | 300.0 | 5.5 | 123.7 | 0.66 | 0.32 |
| 실시예(39) | 화합물(1-39) | 4.8 | 5.5 | 300.0 | 5.5 | 137.3 | 0.66 | 0.32 |
| 실시예(40) | 화합물(1-40) | 5.2 | 5.3 | 300.0 | 5.7 | 126.0 | 0.66 | 0.33 |
| 실시예(41) | 화합물(1-41) | 4.8 | 5.2 | 300.0 | 5.7 | 129.0 | 0.66 | 0.33 |
| 실시예(42) | 화합물(1-42) | 4.9 | 5.3 | 300.0 | 5.7 | 132.1 | 0.66 | 0.32 |
| 실시예(43) | 화합물(1-43) | 5.0 | 5.5 | 300.0 | 5.5 | 126.7 | 0.66 | 0.32 |
| 실시예(44) | 화합물(1-44) | 5.1 | 5.3 | 300.0 | 5.6 | 141.1 | 0.66 | 0.32 |
| 실시예(45) | 화합물(1-45) | 4.8 | 5.6 | 300.0 | 5.4 | 132.2 | 0.66 | 0.32 |
| 실시예(46) | 화합물(1-46) | 5.2 | 5.3 | 300.0 | 5.6 | 129.0 | 0.66 | 0.33 |
| 실시예(47) | 화합물(1-47) | 5.0 | 5.5 | 300.0 | 5.5 | 149.0 | 0.66 | 0.33 |
| 실시예(48) | 화합물(1-48) | 5.2 | 5.2 | 300.0 | 5.7 | 120.6 | 0.66 | 0.33 |
| 실시예(49) | 화합물(1-49) | 4.9 | 5.3 | 300.0 | 5.7 | 140.5 | 0.66 | 0.32 |
| 실시예(50) | 화합물(1-50) | 5.0 | 5.6 | 300.0 | 5.4 | 138.1 | 0.66 | 0.33 |
| 실시예(51) | 화합물(1-51) | 4.8 | 5.4 | 300.0 | 5.5 | 119.2 | 0.66 | 0.32 |
| 실시예(52) | 화합물(1-52) | 5.2 | 5.6 | 300.0 | 5.4 | 141.4 | 0.66 | 0.32 |
| 실시예(53) | 화합물(1-53) | 5.1 | 5.4 | 300.0 | 5.6 | 139.8 | 0.66 | 0.33 |
| 실시예(54) | 화합물(1-54) | 4.9 | 5.5 | 300.0 | 5.4 | 133.0 | 0.66 | 0.32 |
| 실시예(55) | 화합물(1-55) | 5.0 | 5.3 | 300.0 | 5.7 | 146.3 | 0.66 | 0.32 |
| 실시예(56) | 화합물(1-56) | 4.9 | 5.5 | 300.0 | 5.5 | 138.2 | 0.66 | 0.32 |
| 실시예(57) | 화합물(1-57) | 4.8 | 5.4 | 300.0 | 5.6 | 121.7 | 0.66 | 0.33 |
| 실시예(58) | 화합물(1-58) | 4.8 | 5.6 | 300.0 | 5.3 | 133.5 | 0.66 | 0.32 |
| 실시예(59) | 화합물(1-59) | 5.1 | 5.6 | 300.0 | 5.4 | 133.1 | 0.66 | 0.33 |
| 실시예(60) | 화합물(1-60) | 5.0 | 5.4 | 300.0 | 5.5 | 132.9 | 0.66 | 0.32 |
| 실시예(61) | 화합물(1-61) | 4.9 | 5.4 | 300.0 | 5.5 | 120.5 | 0.66 | 0.32 |
| 실시예(62) | 화합물(1-62) | 5.1 | 5.6 | 300.0 | 5.4 | 116.4 | 0.66 | 0.32 |
| 실시예(63) | 화합물(1-63) | 5.1 | 5.2 | 300.0 | 5.7 | 121.4 | 0.66 | 0.32 |
| 실시예(64) | 화합물(1-64) | 4.8 | 5.4 | 300.0 | 5.5 | 126.4 | 0.66 | 0.32 |
| 실시예(65) | 화합물(1-65) | 4.9 | 5.2 | 300.0 | 5.7 | 134.9 | 0.66 | 0.32 |
| 실시예(66) | 화합물(1-66) | 5.0 | 5.4 | 300.0 | 5.6 | 139.2 | 0.66 | 0.32 |
| 실시예(67) | 화합물(1-67) | 4.8 | 5.3 | 300.0 | 5.7 | 133.7 | 0.66 | 0.32 |
| 실시예(68) | 화합물(1-68) | 5.1 | 5.3 | 300.0 | 5.7 | 120.4 | 0.66 | 0.33 |
| 실시예(69) | 화합물(1-69) | 4.8 | 5.4 | 300.0 | 5.5 | 148.3 | 0.66 | 0.32 |
| 실시예(70) | 화합물(1-70) | 5.1 | 5.6 | 300.0 | 5.3 | 115.3 | 0.66 | 0.32 |
| 실시예(71) | 화합물(1-71) | 5.0 | 5.2 | 300.0 | 5.7 | 116.2 | 0.66 | 0.32 |
| 실시예(72) | 화합물(1-72) | 4.4 | 5.6 | 300.0 | 5.4 | 183.5 | 0.66 | 0.33 |
| 실시예(73) | 화합물(1-73) | 4.9 | 5.6 | 300.0 | 5.4 | 129.4 | 0.66 | 0.33 |
| 실시예(74) | 화합물(1-74) | 4.9 | 5.3 | 300.0 | 5.6 | 137.6 | 0.66 | 0.32 |
| 실시예(75) | 화합물(1-75) | 4.7 | 5.7 | 300.0 | 5.3 | 140.7 | 0.66 | 0.33 |
| 실시예(76) | 화합물(1-76) | 5.2 | 5.3 | 300.0 | 5.7 | 120.1 | 0.66 | 0.33 |
| 실시예(77) | 화합물(1-77) | 4.8 | 5.3 | 300.0 | 5.6 | 136.0 | 0.66 | 0.32 |
| 실시예(78) | 화합물(1-78) | 5.0 | 5.5 | 300.0 | 5.5 | 119.2 | 0.66 | 0.33 |
| 실시예(79) | 화합물(1-79) | 5.1 | 5.2 | 300.0 | 5.7 | 143.0 | 0.66 | 0.32 |
| 실시예(80) | 화합물(1-80) | 4.8 | 5.3 | 300.0 | 5.7 | 123.5 | 0.66 | 0.33 |
| 실시예(81) | 화합물(1-81) | 4.8 | 5.4 | 300.0 | 5.5 | 143.2 | 0.66 | 0.32 |
| 실시예(82) | 화합물(1-82) | 5.1 | 5.4 | 300.0 | 5.6 | 144.5 | 0.66 | 0.33 |
| 실시예(83) | 화합물(1-83) | 5.1 | 5.5 | 300.0 | 5.4 | 142.5 | 0.66 | 0.32 |
| 실시예(84) | 화합물(1-84) | 5.0 | 5.6 | 300.0 | 5.3 | 148.8 | 0.66 | 0.33 |
| 실시예(85) | 화합물(1-85) | 5.2 | 5.5 | 300.0 | 5.4 | 121.7 | 0.66 | 0.32 |
| 실시예(86) | 화합물(1-86) | 5.1 | 5.6 | 300.0 | 5.3 | 117.3 | 0.66 | 0.33 |
| 실시예(87) | 화합물(1-87) | 4.9 | 5.5 | 300.0 | 5.4 | 148.2 | 0.66 | 0.32 |
| 실시예(88) | 화합물(1-88) | 4.8 | 5.5 | 300.0 | 5.5 | 118.3 | 0.66 | 0.32 |
| 실시예(89) | 화합물(1-89) | 5.1 | 5.4 | 300.0 | 5.6 | 132.3 | 0.66 | 0.33 |
| 실시예(90) | 화합물(1-90) | 4.8 | 5.3 | 300.0 | 5.7 | 133.3 | 0.66 | 0.33 |
| 실시예(91) | 화합물(1-91) | 5.0 | 5.6 | 300.0 | 5.3 | 132.9 | 0.66 | 0.32 |
| 실시예(92) | 화합물(1-92) | 5.0 | 5.4 | 300.0 | 5.5 | 121.7 | 0.66 | 0.33 |
| 실시예(93) | 화합물(1-93) | 4.9 | 5.3 | 300.0 | 5.6 | 137.8 | 0.66 | 0.33 |
| 실시예(94) | 화합물(1-94) | 4.9 | 5.5 | 300.0 | 5.5 | 141.2 | 0.66 | 0.33 |
| 실시예(95) | 화합물(1-95) | 5.0 | 5.6 | 300.0 | 5.3 | 141.7 | 0.66 | 0.32 |
| 실시예(96) | 화합물(1-96) | 5.0 | 5.2 | 300.0 | 5.7 | 149.8 | 0.66 | 0.32 |
| 실시예(97) | 화합물(1-97) | 4.9 | 5.6 | 300.0 | 5.4 | 134.3 | 0.66 | 0.32 |
| 실시예(98) | 화합물(1-98) | 5.1 | 5.6 | 300.0 | 5.3 | 117.6 | 0.66 | 0.33 |
| 실시예(99) | 화합물(1-99) | 4.9 | 5.3 | 300.0 | 5.6 | 133.9 | 0.66 | 0.33 |
| 실시예(100) | 화합물(1-100) | 4.9 | 5.4 | 300.0 | 5.6 | 143.9 | 0.66 | 0.33 |
| 실시예(101) | 화합물(1-101) | 5.1 | 5.5 | 300.0 | 5.4 | 148.9 | 0.66 | 0.32 |
| 실시예(102) | 화합물(1-102) | 5.2 | 5.4 | 300.0 | 5.6 | 126.8 | 0.66 | 0.32 |
| 실시예(103) | 화합물(1-103) | 4.9 | 5.2 | 300.0 | 5.7 | 129.5 | 0.66 | 0.32 |
| 실시예(104) | 화합물(1-104) | 5.0 | 5.4 | 300.0 | 5.6 | 132.6 | 0.66 | 0.33 |
| 실시예(105) | 화합물(1-105) | 5.0 | 5.3 | 300.0 | 5.6 | 140.5 | 0.66 | 0.33 |
| 실시예(106) | 화합물(1-106) | 4.9 | 5.2 | 300.0 | 5.7 | 117.6 | 0.66 | 0.33 |
| 실시예(107) | 화합물(1-107) | 5.1 | 5.5 | 300.0 | 5.4 | 162.3 | 0.66 | 0.33 |
| 실시예(108) | 화합물(1-108) | 5.0 | 5.5 | 300.0 | 5.4 | 169.4 | 0.66 | 0.32 |
| 실시예(109) | 화합물(1-109) | 5.0 | 5.3 | 300.0 | 5.7 | 133.2 | 0.66 | 0.32 |
| 실시예(110) | 화합물(1-110) | 4.8 | 5.6 | 300.0 | 5.3 | 129.1 | 0.66 | 0.33 |
| 실시예(111) | 화합물(1-111) | 4.9 | 5.6 | 300.0 | 5.3 | 139.0 | 0.66 | 0.32 |
| 실시예(112) | 화합물(1-112) | 5.0 | 5.2 | 300.0 | 5.7 | 124.4 | 0.66 | 0.33 |
| 실시예(113) | 화합물(1-113) | 4.9 | 5.4 | 300.0 | 5.6 | 145.9 | 0.66 | 0.33 |
| 실시예(114) | 화합물(1-114) | 4.8 | 5.5 | 300.0 | 5.4 | 148.8 | 0.66 | 0.32 |
| 실시예(115) | 화합물(1-115) | 5.0 | 5.7 | 300.0 | 5.3 | 117.8 | 0.66 | 0.32 |
| 실시예(116) | 화합물(1-116) | 4.8 | 5.6 | 300.0 | 5.4 | 116.0 | 0.66 | 0.32 |
| 실시예(117) | 화합물(1-117) | 5.1 | 5.4 | 300.0 | 5.5 | 128.8 | 0.66 | 0.32 |
| 실시예(118) | 화합물(1-118) | 5.0 | 5.3 | 300.0 | 5.7 | 122.4 | 0.66 | 0.32 |
| 실시예(119) | 화합물(1-119) | 4.9 | 5.2 | 300.0 | 5.7 | 149.4 | 0.66 | 0.33 |
| 실시예(120) | 화합물(1-120) | 4.8 | 5.5 | 300.0 | 5.5 | 122.3 | 0.66 | 0.33 |
| 실시예(121) | 화합물(1-121) | 4.7 | 5.6 | 300.0 | 5.4 | 128.7 | 0.66 | 0.32 |
| 실시예(122) | 화합물(1-122) | 4.8 | 5.4 | 300.0 | 5.6 | 121.9 | 0.66 | 0.32 |
| 실시예(123) | 화합물(1-123) | 4.9 | 5.6 | 300.0 | 5.4 | 121.6 | 0.66 | 0.33 |
| 실시예(124) | 화합물(1-124) | 5.0 | 5.2 | 300.0 | 5.7 | 135.0 | 0.66 | 0.33 |
| 실시예(125) | 화합물(1-125) | 4.7 | 5.3 | 300.0 | 5.7 | 135.9 | 0.66 | 0.32 |
| 실시예(126) | 화합물(1-126) | 4.8 | 5.6 | 300.0 | 5.3 | 116.7 | 0.66 | 0.32 |
| 실시예(127) | 화합물(1-127) | 4.9 | 5.6 | 300.0 | 5.4 | 148.5 | 0.66 | 0.32 |
| 실시예(128) | 화합물(1-128) | 5.0 | 5.6 | 300.0 | 5.3 | 133.9 | 0.66 | 0.33 |
| 실시예(129) | 화합물(1-129) | 4.7 | 5.4 | 300.0 | 5.6 | 119.1 | 0.66 | 0.33 |
| 실시예(130) | 화합물(1-130) | 4.8 | 5.5 | 300.0 | 5.4 | 141.0 | 0.66 | 0.32 |
| 실시예(131) | 화합물(1-131) | 4.7 | 5.5 | 300.0 | 5.5 | 124.9 | 0.66 | 0.33 |
| 실시예(132) | 화합물(1-132) | 5.0 | 5.5 | 300.0 | 5.4 | 136.5 | 0.66 | 0.32 |
| 실시예(133) | 화합물(1-133) | 5.1 | 5.5 | 300.0 | 5.4 | 149.6 | 0.66 | 0.33 |
| 실시예(134) | 화합물(1-134) | 5.1 | 5.2 | 300.0 | 5.7 | 121.8 | 0.66 | 0.32 |
| 실시예(135) | 화합물(1-135) | 4.9 | 5.6 | 300.0 | 5.4 | 116.6 | 0.66 | 0.32 |
| 실시예(136) | 화합물(1-136) | 4.8 | 5.5 | 300.0 | 5.5 | 144.3 | 0.66 | 0.33 |
| 실시예(137) | 화합물(1-137) | 5.2 | 5.5 | 300.0 | 5.5 | 142.0 | 0.66 | 0.32 |
| 실시예(138) | 화합물(1-138) | 5.2 | 5.5 | 300.0 | 5.5 | 144.8 | 0.66 | 0.33 |
| 실시예(139) | 화합물(1-139) | 4.7 | 5.6 | 300.0 | 5.4 | 118.2 | 0.66 | 0.32 |
| 실시예(140) | 화합물(1-140) | 4.9 | 5.6 | 300.0 | 5.4 | 142.0 | 0.66 | 0.32 |
| 실시예(141) | 화합물(1-141) | 4.9 | 5.5 | 300.0 | 5.5 | 117.2 | 0.66 | 0.32 |
| 실시예(142) | 화합물(1-142) | 4.9 | 5.3 | 300.0 | 5.7 | 135.8 | 0.66 | 0.32 |
| 실시예(143) | 화합물(1-143) | 4.8 | 5.7 | 300.0 | 5.3 | 142.3 | 0.66 | 0.33 |
| 실시예(144) | 화합물(1-144) | 5.1 | 5.4 | 300.0 | 5.6 | 120.7 | 0.66 | 0.32 |
| 실시예(145) | 화합물(1-145) | 4.8 | 5.5 | 300.0 | 5.5 | 117.3 | 0.66 | 0.33 |
| 실시예(146) | 화합물(1-146) | 4.7 | 5.3 | 300.0 | 5.6 | 123.9 | 0.66 | 0.33 |
| 실시예(147) | 화합물(1-147) | 4.8 | 5.2 | 300.0 | 5.7 | 123.4 | 0.66 | 0.33 |
| 실시예(148) | 화합물(1-148) | 4.7 | 5.4 | 300.0 | 5.6 | 123.3 | 0.66 | 0.33 |
| 실시예(149) | 화합물(1-149) | 4.8 | 5.4 | 300.0 | 5.6 | 132.2 | 0.66 | 0.32 |
| 실시예(150) | 화합물(1-150) | 5.1 | 5.3 | 300.0 | 5.7 | 130.5 | 0.66 | 0.33 |
| compound | Driving voltage | Current (mA / cm2) | Luminance (cd / m2) | Efficiency (cd / A) | T (90) | CIE | ||
| x | y | |||||||
| Comparative Example (2) | Comparative Compound 2 | 5.7 | 7.2 | 300.0 | 4.2 | 99.1 | 0.66 | 0.32 |
| Comparative Example (3) | Comparative Compound 3 | 5.6 | 7.5 | 300.0 | 4.0 | 95.1 | 0.66 | 0.32 |
| Comparative Example (4) | Comparative Compound 4 | 5.7 | 8.5 | 300.0 | 3.5 | 108.7 | 0.66 | 0.32 |
| Comparative Example (5) | Comparative Compound 5 | 5.6 | 8.2 | 300.0 | 3.7 | 91.8 | 0.66 | 0.32 |
| Comparative Example (6) | Do not use | 4.5 | 6.5 | 300 | 4.6 | 91.6 | 0.66 | 0.32 |
| Example (1) | Compound (1-1) | 5.0 | 5.3 | 300.0 | 5.7 | 158.9 | 0.66 | 0.33 |
| Example (2) | Compound (1-2) | 4.9 | 5.3 | 300.0 | 5.7 | 162.6 | 0.66 | 0.32 |
| Example (3) | Compound (1-3) | 4.9 | 5.6 | 300.0 | 5.3 | 122.0 | 0.66 | 0.33 |
| Example (4) | Compound (1-4) | 4.5 | 5.4 | 300.0 | 5.6 | 157.7 | 0.66 | 0.32 |
| Example (5) | Compound (1-5) | 4.3 | 4.4 | 300.0 | 6.8 | 180.9 | 0.66 | 0.32 |
| Example (6) | Compound (1-6) | 4.3 | 4.5 | 300.0 | 6.7 | 191.0 | 0.66 | 0.32 |
| Example (7) | Compound (1-7) | 4.7 | 5.6 | 300.0 | 5.4 | 131.5 | 0.66 | 0.33 |
| Example (8) | Compound (1-8) | 4.8 | 5.3 | 300.0 | 5.7 | 119.8 | 0.66 | 0.32 |
| Example (9) | Compound (1-9) | 5.2 | 5.3 | 300.0 | 5.7 | 147.5 | 0.66 | 0.32 |
| Example (10) | Compound (1-10) | 4.9 | 5.5 | 300.0 | 5.4 | 138.4 | 0.66 | 0.32 |
| Example (11) | Compound (1-11) | 4.8 | 5.5 | 300.0 | 5.5 | 146.1 | 0.66 | 0.32 |
| Example (12) | Compound (1-12) | 4.7 | 5.5 | 300.0 | 5.4 | 140.8 | 0.66 | 0.33 |
| Example (13) | Compound (1-13) | 4.8 | 5.4 | 300.0 | 5.5 | 138.7 | 0.66 | 0.32 |
| Example (14) | Compound (1-14) | 4.4 | 5.4 | 300.0 | 5.6 | 178.9 | 0.66 | 0.33 |
| Example (15) | Compound (1-15) | 5.0 | 5.5 | 300.0 | 5.5 | 116.1 | 0.66 | 0.33 |
| Example (16) | Compound (1-16) | 5.1 | 5.6 | 300.0 | 5.4 | 147.9 | 0.66 | 0.33 |
| Example (17) | Compound (1-17) | 4.8 | 5.5 | 300.0 | 5.4 | 127.1 | 0.66 | 0.32 |
| Example (18) | Compound (1-18) | 4.9 | 5.3 | 300.0 | 5.7 | 121.1 | 0.66 | 0.32 |
| Example (19) | Compound (1-19) | 5.1 | 5.4 | 300.0 | 5.6 | 134.3 | 0.66 | 0.32 |
| Example (20) | Compound (1-20) | 4.9 | 5.4 | 300.0 | 5.6 | 119.7 | 0.66 | 0.33 |
| Example (21) | Compound (1-21) | 5.0 | 5.6 | 300.0 | 5.4 | 140.7 | 0.66 | 0.32 |
| Example (22) | Compound (1-22) | 4.9 | 5.6 | 300.0 | 5.3 | 144.9 | 0.66 | 0.32 |
| Example (23) | Compound (1-23) | 5.2 | 5.7 | 300.0 | 5.3 | 146.8 | 0.66 | 0.32 |
| Example (24) | Compound (1-24) | 5.1 | 5.3 | 300.0 | 5.6 | 129.1 | 0.66 | 0.33 |
| Example (25) | Compound (1-25) | 5.2 | 5.6 | 300.0 | 5.4 | 125.4 | 0.66 | 0.33 |
| Example (26) | Compound (1-26) | 5.2 | 5.4 | 300.0 | 5.6 | 138.2 | 0.66 | 0.33 |
| Example (27) | Compound (1-27) | 5.0 | 5.6 | 300.0 | 5.3 | 142.6 | 0.66 | 0.32 |
| Example (28) | Compound (1-28) | 5.0 | 5.3 | 300.0 | 5.7 | 145.4 | 0.66 | 0.33 |
| Example (29) | Compound (1-29) | 5.0 | 5.5 | 300.0 | 5.4 | 132.4 | 0.66 | 0.33 |
| Example (30) | Compound (1-30) | 4.8 | 5.6 | 300.0 | 5.3 | 131.6 | 0.66 | 0.33 |
| Example (31) | Compound (1-31) | 5.0 | 5.4 | 300.0 | 5.5 | 145.3 | 0.66 | 0.32 |
| Example (32) | Compound (1-32) | 5.1 | 5.4 | 300.0 | 5.6 | 144.8 | 0.66 | 0.32 |
| Example (33) | Compound (1-33) | 5.1 | 5.6 | 300.0 | 5.3 | 125.7 | 0.66 | 0.33 |
| Example (34) | Compound (1-34) | 4.7 | 5.4 | 300.0 | 5.6 | 129.3 | 0.66 | 0.33 |
| Example (35) | Compound (1-35) | 4.7 | 5.6 | 300.0 | 5.3 | 124.4 | 0.66 | 0.32 |
| Example (36) | Compound (1-36) | 4.9 | 5.4 | 300.0 | 5.6 | 143.1 | 0.66 | 0.33 |
| Example (37) | Compound (1-37) | 4.9 | 5.6 | 300.0 | 5.3 | 117.6 | 0.66 | 0.32 |
| Example (38) | Compound (1-38) | 4.9 | 5.5 | 300.0 | 5.5 | 123.7 | 0.66 | 0.32 |
| Example (39) | Compound (1-39) | 4.8 | 5.5 | 300.0 | 5.5 | 137.3 | 0.66 | 0.32 |
| Example (40) | Compound (1-40) | 5.2 | 5.3 | 300.0 | 5.7 | 126.0 | 0.66 | 0.33 |
| Example (41) | Compound (1-41) | 4.8 | 5.2 | 300.0 | 5.7 | 129.0 | 0.66 | 0.33 |
| Example (42) | Compound (1-42) | 4.9 | 5.3 | 300.0 | 5.7 | 132.1 | 0.66 | 0.32 |
| Example (43) | Compound (1-43) | 5.0 | 5.5 | 300.0 | 5.5 | 126.7 | 0.66 | 0.32 |
| Example (44) | Compound (1-44) | 5.1 | 5.3 | 300.0 | 5.6 | 141.1 | 0.66 | 0.32 |
| Example (45) | Compound (1-45) | 4.8 | 5.6 | 300.0 | 5.4 | 132.2 | 0.66 | 0.32 |
| Example (46) | Compound (1-46) | 5.2 | 5.3 | 300.0 | 5.6 | 129.0 | 0.66 | 0.33 |
| Example (47) | Compound (1-47) | 5.0 | 5.5 | 300.0 | 5.5 | 149.0 | 0.66 | 0.33 |
| Example (48) | Compound (1-48) | 5.2 | 5.2 | 300.0 | 5.7 | 120.6 | 0.66 | 0.33 |
| Example (49) | Compound (1-49) | 4.9 | 5.3 | 300.0 | 5.7 | 140.5 | 0.66 | 0.32 |
| Example (50) | Compound (1-50) | 5.0 | 5.6 | 300.0 | 5.4 | 138.1 | 0.66 | 0.33 |
| Example (51) | Compound (1-51) | 4.8 | 5.4 | 300.0 | 5.5 | 119.2 | 0.66 | 0.32 |
| Example (52) | Compound (1-52) | 5.2 | 5.6 | 300.0 | 5.4 | 141.4 | 0.66 | 0.32 |
| Example (53) | Compound (1-53) | 5.1 | 5.4 | 300.0 | 5.6 | 139.8 | 0.66 | 0.33 |
| Example (54) | Compound (1-54) | 4.9 | 5.5 | 300.0 | 5.4 | 133.0 | 0.66 | 0.32 |
| Example (55) | Compound (1-55) | 5.0 | 5.3 | 300.0 | 5.7 | 146.3 | 0.66 | 0.32 |
| Example (56) | Compound (1-56) | 4.9 | 5.5 | 300.0 | 5.5 | 138.2 | 0.66 | 0.32 |
| Example (57) | Compound (1-57) | 4.8 | 5.4 | 300.0 | 5.6 | 121.7 | 0.66 | 0.33 |
| Example (58) | Compound (1-58) | 4.8 | 5.6 | 300.0 | 5.3 | 133.5 | 0.66 | 0.32 |
| Example (59) | Compound (1-59) | 5.1 | 5.6 | 300.0 | 5.4 | 133.1 | 0.66 | 0.33 |
| Example (60) | Compound (1-60) | 5.0 | 5.4 | 300.0 | 5.5 | 132.9 | 0.66 | 0.32 |
| Example (61) | Compound (1-61) | 4.9 | 5.4 | 300.0 | 5.5 | 120.5 | 0.66 | 0.32 |
| Example (62) | Compound (1-62) | 5.1 | 5.6 | 300.0 | 5.4 | 116.4 | 0.66 | 0.32 |
| Example (63) | Compound (1-63) | 5.1 | 5.2 | 300.0 | 5.7 | 121.4 | 0.66 | 0.32 |
| Example (64) | Compound (1-64) | 4.8 | 5.4 | 300.0 | 5.5 | 126.4 | 0.66 | 0.32 |
| Example (65) | Compound (1-65) | 4.9 | 5.2 | 300.0 | 5.7 | 134.9 | 0.66 | 0.32 |
| Example (66) | Compound (1-66) | 5.0 | 5.4 | 300.0 | 5.6 | 139.2 | 0.66 | 0.32 |
| Example (67) | Compound (1-67) | 4.8 | 5.3 | 300.0 | 5.7 | 133.7 | 0.66 | 0.32 |
| Example (68) | Compound (1-68) | 5.1 | 5.3 | 300.0 | 5.7 | 120.4 | 0.66 | 0.33 |
| Example (69) | Compound (1-69) | 4.8 | 5.4 | 300.0 | 5.5 | 148.3 | 0.66 | 0.32 |
| Example (70) | Compound (1-70) | 5.1 | 5.6 | 300.0 | 5.3 | 115.3 | 0.66 | 0.32 |
| Example (71) | Compound (1-71) | 5.0 | 5.2 | 300.0 | 5.7 | 116.2 | 0.66 | 0.32 |
| Example (72) | Compound (1-72) | 4.4 | 5.6 | 300.0 | 5.4 | 183.5 | 0.66 | 0.33 |
| Example (73) | Compound (1-73) | 4.9 | 5.6 | 300.0 | 5.4 | 129.4 | 0.66 | 0.33 |
| Example (74) | Compound (1-74) | 4.9 | 5.3 | 300.0 | 5.6 | 137.6 | 0.66 | 0.32 |
| Example (75) | Compound (1-75) | 4.7 | 5.7 | 300.0 | 5.3 | 140.7 | 0.66 | 0.33 |
| Example (76) | Compound (1-76) | 5.2 | 5.3 | 300.0 | 5.7 | 120.1 | 0.66 | 0.33 |
| Example (77) | Compound (1-77) | 4.8 | 5.3 | 300.0 | 5.6 | 136.0 | 0.66 | 0.32 |
| Example (78) | Compound (1-78) | 5.0 | 5.5 | 300.0 | 5.5 | 119.2 | 0.66 | 0.33 |
| Example (79) | Compound (1-79) | 5.1 | 5.2 | 300.0 | 5.7 | 143.0 | 0.66 | 0.32 |
| Example (80) | Compound (1-80) | 4.8 | 5.3 | 300.0 | 5.7 | 123.5 | 0.66 | 0.33 |
| Example (81) | Compound (1-81) | 4.8 | 5.4 | 300.0 | 5.5 | 143.2 | 0.66 | 0.32 |
| Example (82) | Compound (1-82) | 5.1 | 5.4 | 300.0 | 5.6 | 144.5 | 0.66 | 0.33 |
| Example (83) | Compound (1-83) | 5.1 | 5.5 | 300.0 | 5.4 | 142.5 | 0.66 | 0.32 |
| Example (84) | Compound (1-84) | 5.0 | 5.6 | 300.0 | 5.3 | 148.8 | 0.66 | 0.33 |
| Example (85) | Compound (1-85) | 5.2 | 5.5 | 300.0 | 5.4 | 121.7 | 0.66 | 0.32 |
| Example (86) | Compound (1-86) | 5.1 | 5.6 | 300.0 | 5.3 | 117.3 | 0.66 | 0.33 |
| Example (87) | Compound (1-87) | 4.9 | 5.5 | 300.0 | 5.4 | 148.2 | 0.66 | 0.32 |
| Example (88) | Compound (1-88) | 4.8 | 5.5 | 300.0 | 5.5 | 118.3 | 0.66 | 0.32 |
| Example (89) | Compound (1-89) | 5.1 | 5.4 | 300.0 | 5.6 | 132.3 | 0.66 | 0.33 |
| Example (90) | Compound (1-90) | 4.8 | 5.3 | 300.0 | 5.7 | 133.3 | 0.66 | 0.33 |
| Example (91) | Compound (1-91) | 5.0 | 5.6 | 300.0 | 5.3 | 132.9 | 0.66 | 0.32 |
| Example (92) | Compound (1-92) | 5.0 | 5.4 | 300.0 | 5.5 | 121.7 | 0.66 | 0.33 |
| Example (93) | Compound (1-93) | 4.9 | 5.3 | 300.0 | 5.6 | 137.8 | 0.66 | 0.33 |
| Example (94) | Compound (1-94) | 4.9 | 5.5 | 300.0 | 5.5 | 141.2 | 0.66 | 0.33 |
| Example (95) | Compound (1-95) | 5.0 | 5.6 | 300.0 | 5.3 | 141.7 | 0.66 | 0.32 |
| Example (96) | Compound (1-96) | 5.0 | 5.2 | 300.0 | 5.7 | 149.8 | 0.66 | 0.32 |
| Example (97) | Compound (1-97) | 4.9 | 5.6 | 300.0 | 5.4 | 134.3 | 0.66 | 0.32 |
| Example (98) | Compound (1-98) | 5.1 | 5.6 | 300.0 | 5.3 | 117.6 | 0.66 | 0.33 |
| Example (99) | Compound (1-99) | 4.9 | 5.3 | 300.0 | 5.6 | 133.9 | 0.66 | 0.33 |
| Example (100) | Compound (1-100) | 4.9 | 5.4 | 300.0 | 5.6 | 143.9 | 0.66 | 0.33 |
| Example (101) | Compound (1-101) | 5.1 | 5.5 | 300.0 | 5.4 | 148.9 | 0.66 | 0.32 |
| Example (102) | Compound (1-102) | 5.2 | 5.4 | 300.0 | 5.6 | 126.8 | 0.66 | 0.32 |
| Example (103) | Compound (1-103) | 4.9 | 5.2 | 300.0 | 5.7 | 129.5 | 0.66 | 0.32 |
| Example (104) | Compound (1-104) | 5.0 | 5.4 | 300.0 | 5.6 | 132.6 | 0.66 | 0.33 |
| Example 105 | Compound (1-105) | 5.0 | 5.3 | 300.0 | 5.6 | 140.5 | 0.66 | 0.33 |
| Example 106 | Compound (1-106) | 4.9 | 5.2 | 300.0 | 5.7 | 117.6 | 0.66 | 0.33 |
| Example 107 | Compound (1-107) | 5.1 | 5.5 | 300.0 | 5.4 | 162.3 | 0.66 | 0.33 |
| Example 108 | Compound (1-108) | 5.0 | 5.5 | 300.0 | 5.4 | 169.4 | 0.66 | 0.32 |
| Example 109 | Compound (1-109) | 5.0 | 5.3 | 300.0 | 5.7 | 133.2 | 0.66 | 0.32 |
| Example (110) | Compound (1-110) | 4.8 | 5.6 | 300.0 | 5.3 | 129.1 | 0.66 | 0.33 |
| Example (111) | Compound (1-111) | 4.9 | 5.6 | 300.0 | 5.3 | 139.0 | 0.66 | 0.32 |
| Example (112) | Compound (1-112) | 5.0 | 5.2 | 300.0 | 5.7 | 124.4 | 0.66 | 0.33 |
| Example (113) | Compound (1-113) | 4.9 | 5.4 | 300.0 | 5.6 | 145.9 | 0.66 | 0.33 |
| Example 114 | Compound (1-114) | 4.8 | 5.5 | 300.0 | 5.4 | 148.8 | 0.66 | 0.32 |
| Example 115 | Compound (1-115) | 5.0 | 5.7 | 300.0 | 5.3 | 117.8 | 0.66 | 0.32 |
| Example 116 | Compound (1-116) | 4.8 | 5.6 | 300.0 | 5.4 | 116.0 | 0.66 | 0.32 |
| Example 117 | Compound (1-117) | 5.1 | 5.4 | 300.0 | 5.5 | 128.8 | 0.66 | 0.32 |
| Example 118 | Compound (1-118) | 5.0 | 5.3 | 300.0 | 5.7 | 122.4 | 0.66 | 0.32 |
| Example (119) | Compound (1-119) | 4.9 | 5.2 | 300.0 | 5.7 | 149.4 | 0.66 | 0.33 |
| Example 120 | Compound (1-120) | 4.8 | 5.5 | 300.0 | 5.5 | 122.3 | 0.66 | 0.33 |
| Example (121) | Compound (1-121) | 4.7 | 5.6 | 300.0 | 5.4 | 128.7 | 0.66 | 0.32 |
| Example (122) | Compound (1-122) | 4.8 | 5.4 | 300.0 | 5.6 | 121.9 | 0.66 | 0.32 |
| Example (123) | Compound (1-123) | 4.9 | 5.6 | 300.0 | 5.4 | 121.6 | 0.66 | 0.33 |
| Example 124 | Compound (1-124) | 5.0 | 5.2 | 300.0 | 5.7 | 135.0 | 0.66 | 0.33 |
| Example (125) | Compound (1-125) | 4.7 | 5.3 | 300.0 | 5.7 | 135.9 | 0.66 | 0.32 |
| Example 126 | Compound (1-126) | 4.8 | 5.6 | 300.0 | 5.3 | 116.7 | 0.66 | 0.32 |
| Example (127) | Compound (1-127) | 4.9 | 5.6 | 300.0 | 5.4 | 148.5 | 0.66 | 0.32 |
| Example 128 | Compound (1-128) | 5.0 | 5.6 | 300.0 | 5.3 | 133.9 | 0.66 | 0.33 |
| Example (129) | Compound (1-129) | 4.7 | 5.4 | 300.0 | 5.6 | 119.1 | 0.66 | 0.33 |
| Example 130 | Compound (1-130) | 4.8 | 5.5 | 300.0 | 5.4 | 141.0 | 0.66 | 0.32 |
| Example 131 | Compound (1-131) | 4.7 | 5.5 | 300.0 | 5.5 | 124.9 | 0.66 | 0.33 |
| Example 132 | Compound (1-132) | 5.0 | 5.5 | 300.0 | 5.4 | 136.5 | 0.66 | 0.32 |
| Example (133) | Compound (1-133) | 5.1 | 5.5 | 300.0 | 5.4 | 149.6 | 0.66 | 0.33 |
| Example 134 | Compound (1-134) | 5.1 | 5.2 | 300.0 | 5.7 | 121.8 | 0.66 | 0.32 |
| Example (135) | Compound (1-135) | 4.9 | 5.6 | 300.0 | 5.4 | 116.6 | 0.66 | 0.32 |
| Example 136 | Compound (1-136) | 4.8 | 5.5 | 300.0 | 5.5 | 144.3 | 0.66 | 0.33 |
| Example (137) | Compound (1-137) | 5.2 | 5.5 | 300.0 | 5.5 | 142.0 | 0.66 | 0.32 |
| Example (138) | Compound (1-138) | 5.2 | 5.5 | 300.0 | 5.5 | 144.8 | 0.66 | 0.33 |
| Example (139) | Compound (1-139) | 4.7 | 5.6 | 300.0 | 5.4 | 118.2 | 0.66 | 0.32 |
| Example 140 | Compound (1-140) | 4.9 | 5.6 | 300.0 | 5.4 | 142.0 | 0.66 | 0.32 |
| Example 141 | Compound (1-141) | 4.9 | 5.5 | 300.0 | 5.5 | 117.2 | 0.66 | 0.32 |
| Example 142 | Compound (1-142) | 4.9 | 5.3 | 300.0 | 5.7 | 135.8 | 0.66 | 0.32 |
| Example 143 | Compound (1-143) | 4.8 | 5.7 | 300.0 | 5.3 | 142.3 | 0.66 | 0.33 |
| Example 144 | Compound (1-144) | 5.1 | 5.4 | 300.0 | 5.6 | 120.7 | 0.66 | 0.32 |
| Example 145 | Compound (1-145) | 4.8 | 5.5 | 300.0 | 5.5 | 117.3 | 0.66 | 0.33 |
| Example (146) | Compound (1-146) | 4.7 | 5.3 | 300.0 | 5.6 | 123.9 | 0.66 | 0.33 |
| Example (147) | Compound (1-147) | 4.8 | 5.2 | 300.0 | 5.7 | 123.4 | 0.66 | 0.33 |
| Example (148) | Compound (1-148) | 4.7 | 5.4 | 300.0 | 5.6 | 123.3 | 0.66 | 0.33 |
| Example 149 | Compound (1-149) | 4.8 | 5.4 | 300.0 | 5.6 | 132.2 | 0.66 | 0.32 |
| Example (150) | Compound (1-150) | 5.1 | 5.3 | 300.0 | 5.7 | 130.5 | 0.66 | 0.33 |
상기 표 5에서 비교적 높은 효율과 고수명을 보였던 인돌 코어를 적색 인광 발광보조층재료 사용한 결과 상기 표 6에서 다음과 같은 결과를 보여주었다.As a result of using the red phosphorescent auxiliary layer material of the indole core, which showed relatively high efficiency and long life in Table 5, Table 6 shows the following results.
동일한 인돌 코어를 갖더라도 N을 포함하고 있는 헤테로고리기(비교예 2~비교예 5)보다 아릴아민기(본 발명에 따른 화합물)가 main 치환기로 왔을 때 charge balance 유지 및 높은 T1 값을 나타내어 구동전압을 낮추고 엑시톤이 발광층에 잘 머물도록 효과적으로 블로킹을 크게 함으로써 결과적으로 효율과 수명 모두 크게 향상된 것을 볼 수 있다. 또한 발광 보조층을 사용하지 않은 비교예 6보다 효율과 수명이 매우 크게 증가(2배 이상)되는 것을 확인할 수 있었다. Although having the same indole core, when the arylamine group (compound according to the present invention) is the main substituent, the charge balance is maintained and the T1 value is driven, rather than the heterocyclic group containing N (Comparative Examples 2 to 5). By lowering the voltage and effectively blocking the excitons to stay in the light emitting layer, the result is a significant improvement in both efficiency and lifetime. In addition, it was confirmed that the efficiency and lifespan are significantly increased (more than two times) compared with Comparative Example 6 without using the emission auxiliary layer.
이는 본 발명의 화합물들이 높은 T1 에너지 레벨과 깊은 HOMO 에너지 레벨을 가지면서 정공이 보다 원활하게 정공수송층에서 발광층으로 수송되고 엑시톤이 발광층 내에 가두어져 발광 누수가 방지되는 역할을 통해 우수한 유기전기발광소자 구현이 가능하기 때문이다.This is because the compounds of the present invention have a high T1 energy level and a deep HOMO energy level, holes are more smoothly transported from the hole transport layer to the light emitting layer, and excitons are confined in the light emitting layer, thereby realizing excellent organic electroluminescent devices. Because this is possible.
마지막으로 인돌 코어를 중심으로 보면, phenyl기가 치환된 인돌 코어는 비치환된 인돌 코어보다 효율 및 수명 등이 개선되었고, 특히 5번 위치에 phenyl기로 치환된 인돌 코어인 본 발명의 화합물 1-5, 1-6등은 낮은 구동전압과 고효율, 고수명을 나타내는 것을 확인할 수 있었다. Finally, when the indole core is centered, the indole core substituted with a phenyl group has improved efficiency and lifespan than the unsubstituted indole core, and the compound 1-5 of the present invention is an indole core substituted with a phenyl group at position 5, The 1-6 lights showed low driving voltage, high efficiency and long life.
이는 동일한 인돌 코어라고 해도 어느 위치에 어느 치환기를 결합시키냐에 따라 band gap 및 전기적 특성, 계면 특성 등이 크게 변화될 수 있다는 것을 나타내고 있으며, 특히 발광 보조층의 경우 정공 수송층 및 발광층(호스트)과의 상호관계를 파악해야 하는 바, 유사한 코어를 사용하더라도 본 발명에 따른 화합물이 사용된 발광 보조층에서 나타내는 특징을 유추하는 것은 통상의 기술자라 하더라도 매우 어렵다고 할 것이다.This indicates that even in the same indole core, band gaps, electrical characteristics, and interface characteristics can be greatly changed depending on which substituents are bonded to each position. Particularly, in the case of the light emitting auxiliary layer, Since it is necessary to grasp the interrelationship, even if a similar core is used, it will be very difficult even for a person skilled in the art to infer the characteristics indicated in the light emitting auxiliary layer in which the compound according to the present invention is used.
상기와 같이 본 발명에 따른 화합물을 유기전기소자에 적용할 경우 우수한 소자특성을 보이므로, 본 발명에 따른 화합물은 유기전기 발광소자(OLED)뿐만 아니라, 디스플레이장치, 유기태양전지, 유기감광체(OPC), 유기트랜지스터(유기 TFT), 단색 또는 백색 조명용 소자 등에도 사용될 수 있다. 또한, 본 발명에 따른 화합물은 정공 수송층이나 발광 보조층 이외에, 정공 주입층, 발광층, 버퍼층, 전자 주입층, 전자 수송층 등에 사용되더라도 동일한 효과를 얻을 수 있을 것이다.As described above, when the compound according to the present invention is applied to an organic electroluminescent device, the device exhibits excellent device characteristics. ), Organic transistors (organic TFTs), monochromatic or white lighting elements, and the like. In addition, the compound according to the present invention, in addition to the hole transport layer or the light emission auxiliary layer, The same effect may be obtained even when used in a hole injection layer, a light emitting layer, a buffer layer, an electron injection layer, an electron transport layer, and the like.
이상, 본 발명을 예시적으로 설명하였으며, 본 발명이 속하는 기술분야에서 통상의 지식을 가지는 자라면 본 발명의 본질적인 특성에서 벗어나지 않는 범위에서 다양한 변형이 가능할 것이다. 따라서, 본 명세서에 개시된 실시예들은 본 발명을 한정하기 위한 것이 아니라 설명하기 위한 것이고, 이러한 실시예에 의하여 본 발명의 사상과 범위가 한정되는 것은 아니다. 본 발명의 보호범위는 아래의 청구범위에 의하여 해석되어야 하며, 그와 동등한 범위 내에 있는 모든 기술은 본 발명의 권리범위에 포함하는 것으로 해석되어야 할 것이다.The present invention has been described above by way of example, and those skilled in the art will appreciate that various modifications may be made without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are not intended to limit the present invention but to describe the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The protection scope of the present invention should be interpreted by the following claims, and all the technologies within the equivalent scope should be interpreted as being included in the scope of the present invention.
[부호의 설명][Description of the code]
100 : 유기전기소자 110 : 기판100: organic electric element 110: substrate
120 : 양극 130 : 정공주입층120: anode 130: hole injection layer
140 : 정공수송층 141 : 버퍼층140: hole transport layer 141: buffer layer
150 : 발광층 151 : 발광보조층150 light emitting layer 151 light emitting auxiliary layer
160 : 전자수송층 170 : 전자주입층160: electron transport layer 170: electron injection layer
CROSS-REFERENCE TO RELATED APPLICATIONCROSS-REFERENCE TO RELATED APPLICATION
본 특허출원은 2012년 01월 18일 한국에 출원한 특허출원번호 제 10-2012-0005563 호, 2012년 08월 01일 한국에 출원한 특허출원번호 제 10-2012-0084503 호, 2012년 08월 02일 한국에 출원한 특허출원번호 제 10-2012-0084945 호 및 2012년 08월 17일 한국에 출원한 특허출원번호 제 10-2012-0090101 호에 대해 미국 특허법 119(a)조 (35 U.S.C § 119(a))에 따라 우선권을 주장하며, 그 모든 내용은 참고문헌으로 본 특허출원에 병합된다. 아울러, 본 특허출원은 미국 이외에 국가에 대해서도 위와 동일한 이유로 우선권을 주장하면 그 모든 내용은 참고문헌으로 본 특허출원에 병합된다.This patent application is filed with a patent application No. 10-2012-0005563 filed in Korea on Jan. 18, 2012, and a patent application No. 10-2012-0084503 filed in Korea on Aug. 1, 2012, Aug. 2012 119 (a) (35 USC §) to US Patent Application No. 10-2012-0084945 filed in Korea and Korean Patent Application No. 10-2012-0090101 filed in Korea on August 17, 2012 Priority is claimed under 119 (a)), the contents of which are hereby incorporated by reference in their entirety. In addition, if this patent application claims priority for the same reason for countries other than the United States, all its contents are incorporated into this patent application by reference.
Claims (13)
- 양극, 음극, 및 상기 양극과 음극 사이에 형성된 유기물층을 포함하는 유기전기소자에 있어서, An organic electric device comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode.상기 유기물층은, 발광층과 상기 양극 사이에 형성되며 하기 화학식 1로 표시되는 화합물을 함유하는 발광보조층과, 상기 발광보조층과 상기 양극 사이에 형성되며 하기 화학식 2로 표시되는 화합물을 함유하는 정공수송층을 포함하는 것을 특징으로 하는 유기전기소자.The organic material layer is formed between the light emitting layer and the anode and includes a light emitting auxiliary layer containing a compound represented by the following Chemical Formula 1, and a hole transport layer formed between the light emitting auxiliary layer and the anode and containing the compound represented by the following Chemical Formula 2. An organic electric element comprising a.<화학식 1> <Formula 1>
<화학식 2> <Formula 2>
(상기 화학식 2에서, Ar3는,
또는
이다.)(In Formula 2, Ar 3 is
,orto be.)상기 화학식에서, In the above formula,n, o 및 p는 1~4의 정수이고, m은 1 또는 2의 정수이며, m, n, o, p 2 이상인 경우 복수의 R1, R2, R3 또는 R4는 각각 서로 동일하거나 상이하고, i) R1, R2, R3 및 R4 는 각각 서로 독립적으로 수소; 중수소; 삼중수소; 할로겐기; C6~C60의 아릴기; C1~C50의 알킬기; C2~C40의 알케닐기; C6~C60의 아릴아민기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C6~C60의 방향족 고리와 C4~C60의 지방족고리의 축합 고리기; 아민기; 니트로기; 니트릴기; 아미드기 및 실란기로 이루어진 군에서 선택되거나; 또는 ii) 이웃한 R1끼리, 이웃한 R2끼리, 이웃한 R3끼리 및 이웃한 R4끼리 중 적어도 한쌍이 서로 결합하여 적어도 하나의 방향족고리를 형성하며(이때, 방향족고리를 형성하지 않는 R1, R2, R3 및 R4 는 상기 i)에서 정의된 것과 같음)n, o and p are integers from 1 to 4, m is an integer from 1 or 2, and when m, n, o, p 2 or more, a plurality of R 1 , R 2 , R 3 or R 4 are the same as each other or Different from i) R 1 , R 2 , R 3 and R 4 are each independently hydrogen; heavy hydrogen; Tritium; Halogen group; C 6 ~ C 60 Aryl group; C 1 ~ C 50 Alkyl group; C 2 -C 40 alkenyl group; C 6 ~ C 60 arylamine group; C 2 ~ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Condensed ring groups of C 6 -C 60 aromatic rings and C 4 -C 60 aliphatic rings; Amine group; Nitro group; Nitrile group; An amide group and a silane group; Or ii) at least one pair of neighboring R 1 , neighboring R 2 , neighboring R 3, and neighboring R 4 combine with each other to form at least one aromatic ring (wherein the aromatic ring does not form) R 1 , R 2 , R 3 and R 4 are as defined in i) above)L은 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; C3~C60의 헤테로 아릴렌기 및 2가의 지방족 탄화수소;로 이루어진 군에서 선택되며(이들 각각은 수소, 중수소, 삼중수소, 니트로, 니트릴, 할로겐, 아세틸렌기, C7~C20의 아릴알킬기, C8~C20의 아릴알케닐기, C1~C50의 알킬기, C2~C20의 알케닐기 C1~C20의 알콕시기, C6~C20의 아릴기, C2~C20의 헤테로 고리기 및 아미노기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환기로 치환될 수 있다),L is a single bond; C 6 ~ C 60 arylene group; Fluorenylene groups; C 3 ~ C 60 hetero arylene group and a divalent aliphatic hydrocarbon; (each of hydrogen, deuterium, tritium, nitro, nitrile, halogen, acetylene group, C 7 ~ C 20 arylalkyl group, C 8 ~ C 20 aryl alkenyl group, C 1 ~ C 50 Alkyl group, C 2 ~ C 20 Alkenyl group C 1 ~ C 20 Alkoxy group, C 6 ~ C 20 Aryl group, C 2 ~ C 20 May be substituted with a substituent with one or more substituents selected from the group consisting of a heterocyclic group and an amino group),Ar1 내지 Ar7은 각각 서로 독립적으로 C6~C60의 아릴기, O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로아릴기, C2~C20의 알케닐기, 플루오렌일기, C1~C30의 알콕시기, C6~C30의 아릴옥시기, C6~C60의 아릴아민기 및 C1~C50의 알킬기로 이루어진 군에서 선택된다.Ar 1 to Ar 7 are each independently a C 6 ~ C 60 aryl group, C 2 ~ C 60 heteroaryl group containing at least one heteroatom of O, N, S, Si and P, C 2 ~ In the group consisting of C 20 alkenyl group, fluorenyl group, C 1 ~ C 30 alkoxy group, C 6 ~ C 30 aryloxy group, C 6 ~ C 60 arylamine group and C 1 ~ C 50 alkyl group Is selected.(상기 R1 내지 R4 및 Ar1 내지 Ar7가 아릴기인 경우, 이들 각각은 수소, 중수소, 삼중수소, 할로겐기, C1~C60의 알킬기, C1~C60의 알콕시기, C1~C60의 알킬아민기, C6~C60의 아릴아민기, C1~C60의 알킬티오펜기, C6~C60의 아릴 티오펜기, C2~C60의 알케닐기, C2~C60의 알키닐기, C3~C60의 시클로알킬기, C6~C60의 아릴기, 중수소로 치환된 C6~C60의 아릴기, C8~C60의 아릴알케닐기, 치환 또는 비치환된 실란기, 치환 또는 비치환된 붕소기, 치환 또는 비치환된 게르마늄기 및 치환 또는 비치환된 C2~C60의 헤테로고리기로 이루어진 군으로부터 선택된 하나 이상의 기로 치환될 수 있고(단, Ar1 및 Ar2가 아릴기인 경우 상기 치환기 군 중에 중수소, 아미노기, 니트릴기, 니트로기 및 포스핀옥사이드기가 더 포함될 수 있다),(If R 1 to R 4 and Ar 1 to Ar 7 are an aryl group, each of these is hydrogen, deuterium, tritium, halogen, C 1 ~ C 60 alkyl group, C 1 ~ C 60 alkoxy group, C 1 C 60 -C 60 alkylamine group, C 6 -C 60 arylamine group, C 1 -C 60 alkylthiophene group, C 6 -C 60 aryl thiophene group, C 2 -C 60 alkenyl group, C 2 ~ C 60 of the alkynyl group, C 3 ~ C 60 cycloalkyl group, C 6 ~ C 60 aryl group, of a C 6 ~ C 60 substituted by deuterium aryl group, a C 8 ~ arylalkenyl group of C 60, a substituted Or may be substituted with one or more groups selected from the group consisting of an unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted germanium group, and a substituted or unsubstituted C 2 to C 60 heterocyclic group ( , If Ar 1 and Ar 2 is an aryl group, deuterium, amino, nitrile, nitro and phosphine oxide groups may be further included in the substituent group),R1 내지 R4 및 Ar1 내지 Ar7가 헤테로고리기인 경우, 이들 각각은 수소, 중수소, 삼중수소, 할로겐기, C1~C60의 알킬기, C2~C60의 알케닐기, C1~C60의 알콕시기, C1~C60의 알킬아민기, C6~C60의 아릴아민기, C1~C60의 알킬티오기, C6~C60의 아릴기, 중수소로 치환된 C6~C20의 아릴기, C7~C20의 아릴알킬기, C8~C20의 아릴알케닐기, C2~C20의 헤테로 고리기, C2~C60의 알키닐기, 치환 또는 비치환된 실란기, 치환 또는 비치환된 붕소기, 치환 또는 비치환된 게르마늄기,니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있고,ROne To R4 And ArOne To Ar7Is a heterocyclic group, each of these is hydrogen, deuterium, tritium, halogen, COne~ C60Alkyl group, C2~ C60Alkenyl, COne~ C60Alkoxy group, COne~ C60Alkylamine groups, C6~ C60Arylamine group, COne~ C60Alkylthio group, C6~ C60Aryl group of C, substituted with deuterium6~ C20Aryl group, C7~ C20Arylalkyl group, C8~ C20Aryl alkenyl group, C2~ C20Heterocyclic group, C2~ C60It may be substituted with one or more substituents selected from the group consisting of an alkynyl group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted germanium group, a nitrile group and an acetylene group,R1 내지 R4 및 Ar1 내지 Ar7가 알킬기인 경우, 이들 각각은 수소, 중수소, 삼중수소, 할로겐기, C1~C20의 알킬기, C2~C20의 알케닐기, C1~C20의 알콕시기, C6~C20의 아릴기, 중수소로 치환된 C6~C20의 아릴기, C7~C20의 아릴알킬기, C8~C20의 아릴알케닐기, C2~C20의 헤테로 고리기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있고,ROne To R4 And ArOne To Ar7When is an alkyl group, each of these is hydrogen, deuterium, tritium, halogen, COne~ C20Alkyl group, C2~ C20Alkenyl, COne~ C20Alkoxy group, C6~ C20Aryl group of C, substituted with deuterium6~ C20Aryl group, C7~ C20Arylalkyl group, C8~ C20Aryl alkenyl group, C2~ C20It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group, a nitrile group and an acetylene group,R1 내지 R4 및 Ar1 내지 Ar7가 알케닐기인 경우, 이들 각각은 수소, 중수소, 삼중수소, 할로겐기, C1~C20의 알킬기, C2~C20의 알케닐기, C1~C20의 알콕시기, C6~C20의 아릴아민기, C6~C60의 아릴기, 중수소로 치환된 C6~C20의 아릴기, C7~C20의 아릴알킬기, C8~C20의 아릴알케닐기, C2~C20의 헤테로 고리기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있고,ROne To R4 And ArOne To Ar7Is an alkenyl group, each of these is hydrogen, deuterium, tritium, halogen, COne~ C20Alkyl group, C2~ C20Alkenyl, COne~ C20Alkoxy group, C6~ C20Arylamine group, C6~ C60Aryl group of C, substituted with deuterium6~ C20Aryl group, C7~ C20Arylalkyl group, C8~ C20Aryl alkenyl group, C2~ C20It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group, a nitrile group and an acetylene group,R1 내지 R4이 아민기인 경우, 이들 각각은 C1~C60의 알킬기, C2~C60의 알케닐기, C6~C60의 아릴기 및 C8~C60의 아릴알케닐기로 이루어진 군으로부터 선택된 하나 이상의 기로 치환될 수 있고; 아릴렌기는 니트로기, 니트릴기, 할로겐기, C1~C2의 알킬기, C1~C2의 알콕시기, C6~C20의 아릴기, C2~C20의 헤테로 고리기 및 아미노기로 이루어진 군으로부터 선택된 하나 이상의 기로 치환될 수 있고; ROne To R4In the case of this amine group, each of these is COne~ C60Alkyl group, C2~ C60Alkenyl, C6~ C60Aryl group and C8~ C60It may be substituted with one or more groups selected from the group consisting of arylalkenyl group of; Arylene group, nitro group, nitrile group, halogen group, COne~ C2Alkyl group, COne~ C2Alkoxy group, C6~ C20Aryl group, C2~ C20It may be substituted with one or more groups selected from the group consisting of a hetero ring group and an amino group of;R1 내지 R4 및 Ar1 내지 Ar7가 알콕시기인 경우, 이들 각각은 수소, 중수소, 할로겐기, 아미노기, 니트릴기, 니트로기, C1~C20의 알킬기, C2~C20의 알케닐기, C1~C20의 알콕시기, C3~C30의 시클로알킬기, C2~C30의 헤테로시클로알킬기, C6~C60의 아릴기, 중수소로 치환된 C6~C60의 아릴기 및 C2~C60의 헤테로아릴기로 이루어진 군으로부터 선택된 하나 이상의 기로 치환될 수 있고; ROne To R4 And ArOne To Ar7When is an alkoxy group, each of these is hydrogen, deuterium, halogen, amino, nitrile, nitro, COne~ C20Alkyl group, C2~ C20Alkenyl, COne~ C20Alkoxy group, C3~ C30Cycloalkyl group, C2~ C30Heterocycloalkyl group, C6~ C60Aryl group of C, substituted with deuterium6~ C60Aryl group and C2~ C60It may be substituted with one or more groups selected from the group consisting of a heteroaryl group of;상기 Ar1 및 Ar7이 플루오렌일기인 경우, 이들 각각은 수소, 중수소, 삼중수소, 할로겐기, C2~C20의 알케닐기, C1~C20의 알콕시기, C6~C20의 아릴기, 중수소로 치환된 C6~C20의 아릴기, C7~C20의 아릴알킬기, C8~C20의 아릴알케닐기, C1~C50의 알킬기, C2~C20의 헤테로 고리기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있고,When Ar 1 and Ar 7 are fluorenyl groups, each of them is hydrogen, deuterium, tritium, halogen group, C 2 ~ C 20 alkenyl group, C 1 ~ C 20 alkoxy group, C 6 ~ C 20 Aryl group, C 6 ~ C 20 aryl group substituted with deuterium, C 7 ~ C 20 arylalkyl group, C 8 ~ C 20 aryl alkenyl group, C 1 ~ C 50 alkyl group, C 2 ~ C 20 hetero May be substituted with one or more substituents selected from the group consisting of a cyclic group, a nitrile group and an acetylene group,Ar1 내지 Ar7이 아릴옥시기인 경우, 이들 각각은 수소, 중수소, 할로겐기, 아미노기, 니트릴기, 니트로기, C1~C20의 알킬기, C2~C20의 알케닐기, C1~C20의 알콕시기, C3~C30의 시클로알킬기, C2~C30의 헤테로시클로알킬기, C2~C30의 헤테로 고리기, C6~C60의 아릴기, 중수소로 치환된 C6~C60의 아릴기 및 C2~C60의 헤테로아릴기로 이루어진 군으로부터 선택된 하나 이상의 기로 치환될 수 있고; When Ar 1 to Ar 7 are aryloxy groups, each of them is hydrogen, deuterium, halogen group, amino group, nitrile group, nitro group, C 1 ~ C 20 alkyl group, C 2 ~ C 20 alkenyl group, C 1 ~ C 20 alkoxy group, C 3 ~ C 30 cycloalkyl group, C 2 ~ C 30 heterocycloalkyl group, C 2 ~ C 30 heterocyclic group, C 6 ~ C 60 aryl group, C 6 ~ substituted with deuterium heteroaryl group of C 60 aryl group and C 2 ~ C 60 of which can be optionally substituted with one or more groups selected from the group consisting of;R1 내지 R4 및 Ar1 내지 Ar7가 아릴아민기인 경우, 이들 각각은 할로겐기, 아미노기, 니트릴기, 니트로기, C1~C20의 알킬기, C2~C20의 알케닐기, C1~C20의 알콕시기, C3~C30의 시클로알킬기, C2~C30의 헤테로시클로알킬기, C6~C60의 아릴기, 중수소로 치환된 C6~C20의 아릴기 및 C2~C60의 헤테로아릴기로 이루어진 군으로부터 선택된 하나 이상의 기로 치환될 수 있다)ROne To R4 And ArOne To Ar7When is an arylamine group, each of these is a halogen group, an amino group, a nitrile group, a nitro group, COne~ C20Alkyl group, C2~ C20Alkenyl, COne~ C20Alkoxy group, C3~ C30Cycloalkyl group, C2~ C30Heterocycloalkyl group, C6~ C60Aryl group of C, substituted with deuterium6~ C20Aryl group and C2~ C60It may be substituted with one or more groups selected from the group consisting of a heteroaryl group of - 제 1항에 있어서,The method of claim 1,상기 화학식 1의 Ar1 및 Ar2는 하기 그룹에서 선택되는 것을 특징으로 하는 유기전기소자.Ar 1 and Ar 2 of the general formula (1) is an organic electric device, characterized in that selected from the following groups.,
,
,
,
,,,, - 제 1항에 있어서,The method of claim 1,상기 화학식 1과 화학식 2에서, L은 하기 그룹에서 선택되는 것을 특징으로 하는 유기전기소자.In Chemical Formulas 1 and 2, L is selected from the following groups.
- 제 1항에 있어서,The method of claim 1,상기 화학식 1은 하기 화학식 중 하나로 표시되는 것을 특징으로 하는 유기전기소자.Formula 1 is an organic electric device, characterized in that represented by one of the following formula.<화학식 3> <Formula 3>
<화학식 4> <Formula 4>
<화학식 5> <Formula 5>
<화학식 6> <Formula 6>
<화학식 7> <Formula 7>
<화학식 8><Formula 8>
<화학식 9><Formula 9>
(상기 화학식에서, L, Ar1 및 Ar2는 상기 화학식 1에서 정의된 것과 같고,(In the above formula, L, Ar 1 and Ar 2 are the same as defined in Formula 1,a 및 b는 각각 1~5의 정수이며, a 및/또는 b가 2 이상인 경우 복수의 R4 또는 R5는 각각 서로 동일하거나 상이하고, i) R4 및 R5는 각각 서로 독립적으로 C6~C25의 아릴기; 및 C2~C20의 알케닐기로 이루어진 군에서 선택되거나, 또는 ii)이웃한 R4기끼리 및 이웃한 R5기끼리 각각 서로 결합하여 적어도 하나의 고리를 형성하며(이때, 고리를 형성하지 않는 기는 i)에서 정의된 것과 같음),a and b are each an integer of 1 to 5, and when a and / or b are 2 or more, a plurality of R's4 Or R5Are the same as or different from each other, i) R4 And R5Are each independently of each other6~ C25Aryl group; And C2~ C20R is selected from the group consisting of alkenyl groups, or ii)4Chicks and neighboring R5Each group combines with each other to form at least one ring (where a group that does not form a ring is as defined in i),상기 R4 및 R5가 아릴기 또는 알케닐기인 경우, 이들 각각은 수소, C1~C4의 알킬기, C2~C6의 알케닐기 및 C6~C20의 아릴기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있다)When R 4 and R 5 are an aryl group or an alkenyl group, each of them is one selected from the group consisting of hydrogen, an alkyl group of C 1 to C 4 , an alkenyl group of C 2 to C 6 , and an aryl group of C 6 to C 20 May be substituted with more than one substituent) - 제 1항에 있어서,The method of claim 1,상기 화학식 2는 하기 화학식 중 하나로 표시되는 것을 특징으로 하는 유기전기소자.Formula 2 is an organic electric device, characterized in that represented by one of the following formula.
<화학식 14> <Formula 14>
(상기 화학식에서, L, Ar4, Ar5, R3 및 o는 상기 화학식 2에서 정의된 것과 같다)(In the above formula, L, Ar 4 , Ar 5 , R 3 and o are the same as defined in the formula (2)) - 제 1항에 있어서,The method of claim 1,상기 화학식 1은 하기 화합물 중 하나인 것을 특징으로 하는 유기전기소자.Formula 1 is an organic electric device, characterized in that one of the following compounds.
- 제 1항에 있어서,The method of claim 1,상기 화학식 2는 하기 화합물 중 하나인 것을 특징으로 하는 유기전기소자.Formula 2 is an organic electric device, characterized in that one of the following compounds.
- 제 1항에 있어서,The method of claim 1,상기 화합물을 용액공정에 의해 상기 유기물층으로 형성하는 것을 특징으로 하는 유기전기소자.An organic electric device, characterized in that to form the compound to the organic material layer by a solution process.
- 하기 화학식 1로 표시되는 유기전기 발광소자용 화합물.Compound for an organic electroluminescent device represented by the formula (1).화학식 1 Formula 1
상기 화학식에서,In the above formula,m은 1 또는 2의 정수이고, n은 1~4의 정수이며, m 및/또는 n이 2 이상인 경우 복수의 R1 또는 R2는 각각 서로 동일하거나 상이하고, i) R1 및 R2는 각각 서로 독립적으로 수소; 중수소; 삼중수소; 할로겐기; C1~C50의 알킬기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C2~C20의 알케닐기; C6~C60의 아릴기; 및 C6~C60의 아릴아민기;로 이루어진 군에서 선택되거나, 또는 ii)이웃한 R1 끼리 및 이웃한 R2 끼리 서로 결합하여 적어도 하나의 고리를 형성하며(이때, 고리를 형성하지 않는 기는 i)에서 정의된 것과 같음),m is an integer of 1 or 2, n is an integer of 1 to 4, and when m and / or n is 2 or more, a plurality of ROne Or R2Are the same as or different from each other, i) ROne And R2Each independently of one another is hydrogen; heavy hydrogen; Tritium; Halogen group; COne~ C50Alkyl groups; C containing at least one heteroatom of O, N, S, Si and P2~ C60Heterocyclic group of; C2~ C20Alkenyl group; C6~ C60Aryl group; And C6~ C60An arylamine group; selected from the group consisting of ii) neighboring ROne Companion and neighbor R2 They combine with each other to form at least one ring (where a group that does not form a ring is as defined in i),L은 C6~C60의 아릴렌기; 플루오레닐렌기; C3~C60의 헤테로 아릴렌기; 또는 2가의 지방족 탄화수소이며, 이들 각각은 니트로, 니트릴, 할로겐, C1~C20의 알킬기, C1~C20의 알콕시기, C6~C20의 아릴기, C2~C20의 헤테로 고리기 및 아미노기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환기로 치환될 수 있고, L is a C 6 ~ C 60 arylene group; Fluorenylene group; C 3 ~ C 60 Hetero arylene group; Or a divalent aliphatic hydrocarbon, each of which is nitro, nitrile, halogen, C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, C 6 -C 20 aryl group, C 2 -C 20 hetero ring May be substituted with a substituent with one or more substituents selected from the group consisting of a group and an amino group,Ar1 및 Ar2는 C6~C60의 아릴기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C2~C20의 알케닐기; 및 플루오렌일기; 로 이루어진 군에서 선택된다.Ar 1 and Ar 2 are C 6 ~ C 60 An aryl group; C 2 ~ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 2 -C 20 alkenyl group; And fluorenyl groups; It is selected from the group consisting of.(상기 R1, R2, Ar1 및 Ar2가 헤테로고리기인 경우, 이들 각각은 수소, 중수소, 삼중수소, 할로겐기, C1~C20의 알킬기, C2~C20의 알케닐기, C1~C20의 알콕시기, C6~C20의 아릴아민기, C6~C60의 아릴기, 중수소로 치환된 C6~C20의 아릴기, C7~C20의 아릴알킬기, C8~C20의 아릴알케닐기, C2~C20의 헤테로 고리기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있고,(If R 1 , R 2 , Ar 1 and Ar 2 are heterocyclic groups, each of them is hydrogen, deuterium, tritium, halogen, C 1 ~ C 20 alkyl group, C 2 ~ C 20 alkenyl group, C Alkoxy group of 1 to C 20 , C 6 to C 20 arylamine group, C 6 to C 60 aryl group, C 6 to C 20 aryl group substituted with deuterium, C 7 to C 20 arylalkyl group, C 8 to C 20 arylalkenyl group, C 2 ~ C 20 It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group, a nitrile group and an acetylene group,상기 R1, R2, Ar1 및 Ar2가 알케닐기인 경우, 이들 각각은 수소, 중수소, 삼중수소, 할로겐기, C1~C20의 알킬기, C2~C20의 알케닐기, C1~C20의 알콕시기, C6~C20의 아릴아민기, C6~C60의 아릴기, 중수소로 치환된 C6~C20의 아릴기, C7~C20의 아릴알킬기, C8~C20의 아릴알케닐기, C2~C20의 헤테로 고리기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있고,When R 1 , R 2 , Ar 1 and Ar 2 are alkenyl groups, each of them is hydrogen, deuterium, tritium, halogen group, C 1 ~ C 20 alkyl group, C 2 ~ C 20 alkenyl group, C 1 C 6 -C 20 alkoxy group, C 6 -C 20 arylamine group, C 6 -C 60 aryl group, C 6 -C 20 aryl group substituted with deuterium, C 7 -C 20 arylalkyl group, C 8 It may be substituted with one or more substituents selected from the group consisting of arylalkenyl group of ~ C 20 , C 2 ~ C 20 hetero ring group, a nitrile group and an acetylene group,상기 R1, R2, Ar1 및 Ar2가 아릴기인 경우, 이들 각각은 수소, 중수소, 삼중수소, 할로겐기, C1~C20의 알킬기, C1~C20의 알콕시기, C1~C20의 알킬아민기, C1~C20의 알킬티오펜기, C6~C20의 아릴티오펜기, C2~C20의 알케닐기, C2~C20의 알키닐기, C3~C20의 시클로알킬기, C6~C20의 아릴기, 중수소로 치환된 C6~C20의 아릴기, C6~C20의 아릴아민기, C8~C20의 아릴알케닐기, 실란기, 붕소기, 게르마늄기 및 C2~C20의 헤테로고리기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있고(단, Ar1 및 Ar2가 아릴기인 경우 상기 치환기 군 중에 포스핀옥사이드기가 더 포함될 수 있다),When R 1 , R 2 , Ar 1, and Ar 2 are aryl groups, each of them is hydrogen, deuterium, tritium, halogen, C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, C 1- C 20 alkylamine group, C 1 -C 20 alkylthiophene group, C 6 -C 20 arylthiophene group, C 2 -C 20 alkenyl group, C 2 -C 20 alkynyl group, C 3- an aryl group of C 20 cycloalkyl group, C 6 ~ C 20, of a C 6 ~ C 20 substituted by deuterium aryl group, C 6 ~ C 20 aryl amine, C 8 ~ arylalkenyl group of C 20, a silane group , May be substituted with one or more substituents selected from the group consisting of a boron group, a germanium group and a C 2 ~ C 20 heterocyclic group (wherein Ar 1 and Ar 2 is an aryl group, the phosphine oxide group further included Can be)상기 R1 및 R2가 알킬기인 경우, 이들 각각은 수소, 중수소, 삼중수소, 할로겐기, C2~C20의 알케닐기, C1~C20의 알콕시기, C6~C20의 아릴기, 중수소로 치환된 C6~C20의 아릴기, C7~C20의 아릴알킬기, C8~C20의 아릴알케닐기, C2~C20의 헤테로 고리기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있고,When R 1 and R 2 are alkyl groups, each of them is hydrogen, deuterium, tritium, halogen group, C 2 ~ C 20 alkenyl group, C 1 ~ C 20 alkoxy group, C 6 ~ C 20 aryl group , C 6 ~ C 20 aryl group substituted with deuterium, C 7 ~ C 20 arylalkyl group, C 8 ~ C 20 aryl alkenyl group, C 2 ~ C 20 hetero ring group, nitrile group and acetylene group May be substituted with one or more substituents selected from상기 R1 및 R2가 아릴아민기인 경우, 이들 각각은 C6~C20의 아릴기, 중수소로 치환된 C6~C20의 아릴기 및 C2~C20의 헤테로 고리기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있고,When the R 1 and R 2, an aryl amine group, each of which is C 6 ~ C 20 aryl group, of a C 6 ~ C 20 substituted by deuterium aryl group and C 2 ~ C 20 heterocyclic group selected from the group consisting of May be substituted with one or more substituents,상기 Ar1 및 Ar2가 플루오렌일기인 경우, 이들 각각은 수소, 중수소, 삼중수소, 할로겐기, C2~C20의 알케닐기, C1~C20의 알콕시기, C6~C20의 아릴기, 중수소로 치환된 C6~C20의 아릴기, C7~C20의 아릴알킬기, C8~C20의 아릴알케닐기, C1~C50의 알킬기, C2~C20의 헤테로 고리기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있다)When Ar 1 and Ar 2 are fluorenyl groups, each of them is hydrogen, deuterium, tritium, halogen group, C 2 ~ C 20 alkenyl group, C 1 ~ C 20 alkoxy group, C 6 ~ C 20 Aryl group, C 6 ~ C 20 aryl group substituted with deuterium, C 7 ~ C 20 arylalkyl group, C 8 ~ C 20 aryl alkenyl group, C 1 ~ C 50 alkyl group, C 2 ~ C 20 hetero May be substituted with one or more substituents selected from the group consisting of a cyclic group, a nitrile group and an acetylene group) - 제 9항에 있어서,The method of claim 9,하기 화학식 중 하나로 표시되는 것을 특징으로 하는 화합물.Compound represented by one of the following formula.
(상기 화학식에서,(In the above formula,a 및 b는 각각 1~5의 정수이며, a 및/또는 b가 2 이상인 경우 복수의 R4 또는 R5는 각각 서로 동일하거나 상이하고, i) R4 및 R5는 각각 서로 독립적으로 C6~C25의 아릴기; 및 C2~C20의 알케닐기로 이루어진 군에서 선택되거나, 또는 ii)이웃한 R4기끼리 및 이웃한 R5기끼리 각각 서로 결합하여 적어도 하나의 고리를 형성하며(이때, 고리를 형성하지 않는 기는 i)에서 정의된 것과 같음),a and b are each an integer of 1 to 5, and when a and / or b are 2 or more, a plurality of R's4 Or R5Are the same as or different from each other, i) R4 And R5Are each independently of each other6~ C25Aryl group; And C2~ C20R is selected from the group consisting of alkenyl groups, or ii)4Chicks and neighboring R5Each group combines with each other to form at least one ring (where a group that does not form a ring is as defined in i),상기 R4 및 R5가 아릴기 또는 알케닐기인 경우, 이들 각각은 수소, C1~C4의 알킬기, C2~C6의 알케닐기 및 C6~C20의 아릴기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있다)When R 4 and R 5 are an aryl group or an alkenyl group, each of them is one selected from the group consisting of hydrogen, an alkyl group of C 1 to C 4 , an alkenyl group of C 2 to C 6 , and an aryl group of C 6 to C 20 May be substituted with more than one substituent) - 제 1전극, 제 2전극, 및 상기 제 1전극과 제 2전극 사이에 위치하는 유기물층을 포함하는 유기전기소자에 있어서,In an organic electric device comprising a first electrode, a second electrode, and an organic material layer positioned between the first electrode and the second electrode,상기 유기물층은 제 9항의 화합물을 함유하는 것을 특징으로 하는 유기전기소자.The organic material layer is an organic electroluminescent device comprising the compound of claim 9.
- 제 1항의 유기전기소자를 포함하는 디스플레이장치; 및A display device comprising the organic electroluminescent element of claim 1; And상기 디스플레이장치를 구동하는 제어부; 를 포함하는 전자장치.A controller for driving the display device; Electronic device comprising a.
- 제 12항에 있어서,The method of claim 12,상기 유기전기소자는 유기전기발광소자(OLED ), 유기태양전지, 유기감광체(OPC), 유기트랜지스터(유기 TFT), 및 단색 또는 백색 조명용 소자 중 적어도 하나인 것을 특징으로 하는 전자장치.The organic electroluminescent device is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a device for monochrome or white illumination.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14/362,883 US10026905B2 (en) | 2012-01-18 | 2013-01-14 | Compound, organic electric element using the same, and an electronic device thereof |
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20120005563 | 2012-01-18 | ||
| KR10-2012-0005563 | 2012-01-18 | ||
| KR10-2012-0084503 | 2012-08-01 | ||
| KR1020120084503A KR20130084960A (en) | 2012-01-18 | 2012-08-01 | Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof |
| KR10-2012-0084945 | 2012-08-02 | ||
| KR1020120084945A KR101292554B1 (en) | 2012-08-02 | 2012-08-02 | Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof |
| KR10-2012-0090101 | 2012-08-17 | ||
| KR1020120090101A KR101251451B1 (en) | 2012-08-17 | 2012-08-17 | Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2013109027A1 true WO2013109027A1 (en) | 2013-07-25 |
Family
ID=48799411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2013/000280 WO2013109027A1 (en) | 2012-01-18 | 2013-01-14 | Compound, organic electronic element using same and electronic device thereof |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2013109027A1 (en) |
Cited By (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014030921A1 (en) * | 2012-08-21 | 2014-02-27 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescence compounds and organic electroluminescence device containing the same |
| WO2014088352A1 (en) * | 2012-12-06 | 2014-06-12 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
| US20140374711A1 (en) * | 2013-06-14 | 2014-12-25 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| CN105529405A (en) * | 2014-10-17 | 2016-04-27 | 三星显示有限公司 | Organic light emitting component |
| WO2016107459A1 (en) * | 2014-12-29 | 2016-07-07 | Dow Global Technologies Llc | Compositions with 2, 3-disubstituted indoles as charge transport materials, and display devices fabricated therefrom |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| WO2016126035A1 (en) * | 2015-02-03 | 2016-08-11 | 덕산네오룩스 주식회사 | Organic electronic element, and electronic device comprising same |
| US9533984B2 (en) | 2013-04-19 | 2017-01-03 | Incyte Holdings Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US9533954B2 (en) | 2010-12-22 | 2017-01-03 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3 |
| US9580423B2 (en) | 2015-02-20 | 2017-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| US9611267B2 (en) | 2012-06-13 | 2017-04-04 | Incyte Holdings Corporation | Substituted tricyclic compounds as FGFR inhibitors |
| US9708318B2 (en) | 2015-02-20 | 2017-07-18 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| US9748492B2 (en) | 2012-11-02 | 2017-08-29 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
| US9890156B2 (en) | 2015-02-20 | 2018-02-13 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| CN108929261A (en) * | 2017-05-26 | 2018-12-04 | 东进世美肯株式会社 | Coating formation compound and organic luminescent device comprising it |
| CN108976162A (en) * | 2017-05-31 | 2018-12-11 | 东进世美肯株式会社 | Coating formation compound and organic luminescent device comprising it |
| CN109928950A (en) * | 2017-12-19 | 2019-06-25 | 三星显示有限公司 | Organnic electroluminescent device and amine compounds for Organnic electroluminescent device |
| US10411192B2 (en) | 2013-10-11 | 2019-09-10 | Idemitsu Kosan Co., Ltd. | Aromatic amine compound, organic electroluminescent element and electronic device |
| US10611762B2 (en) | 2017-05-26 | 2020-04-07 | Incyte Corporation | Crystalline forms of a FGFR inhibitor and processes for preparing the same |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| CN112079767A (en) * | 2020-09-04 | 2020-12-15 | 江苏三月科技股份有限公司 | Aromatic amine compound and organic electroluminescent device comprising same |
| US11174257B2 (en) | 2018-05-04 | 2021-11-16 | Incyte Corporation | Salts of an FGFR inhibitor |
| CN114315693A (en) * | 2020-09-30 | 2022-04-12 | 江苏三月科技股份有限公司 | Arylamine compound and organic electroluminescent device comprising same |
| US11407750B2 (en) | 2019-12-04 | 2022-08-09 | Incyte Corporation | Derivatives of an FGFR inhibitor |
| US11466004B2 (en) | 2018-05-04 | 2022-10-11 | Incyte Corporation | Solid forms of an FGFR inhibitor and processes for preparing the same |
| US11566028B2 (en) | 2019-10-16 | 2023-01-31 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US11607416B2 (en) | 2019-10-14 | 2023-03-21 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US11628162B2 (en) | 2019-03-08 | 2023-04-18 | Incyte Corporation | Methods of treating cancer with an FGFR inhibitor |
| US11897891B2 (en) | 2019-12-04 | 2024-02-13 | Incyte Corporation | Tricyclic heterocycles as FGFR inhibitors |
| US11939331B2 (en) | 2021-06-09 | 2024-03-26 | Incyte Corporation | Tricyclic heterocycles as FGFR inhibitors |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10310574A (en) * | 1997-05-09 | 1998-11-24 | Minolta Co Ltd | Novel amino compound, its production and use |
| WO2007148660A1 (en) * | 2006-06-22 | 2007-12-27 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device employing heterocycle-containing arylamine derivative |
| WO2008066196A1 (en) * | 2006-11-27 | 2008-06-05 | Fujifilm Corporation | Organic electroluminescent device and indole derivative |
| WO2011102573A1 (en) * | 2010-02-19 | 2011-08-25 | 덕산하이메탈(주) | Compound including indole derivative, organic electronic element using same, and terminal thereof |
-
2013
- 2013-01-14 WO PCT/KR2013/000280 patent/WO2013109027A1/en active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10310574A (en) * | 1997-05-09 | 1998-11-24 | Minolta Co Ltd | Novel amino compound, its production and use |
| WO2007148660A1 (en) * | 2006-06-22 | 2007-12-27 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device employing heterocycle-containing arylamine derivative |
| WO2008066196A1 (en) * | 2006-11-27 | 2008-06-05 | Fujifilm Corporation | Organic electroluminescent device and indole derivative |
| WO2011102573A1 (en) * | 2010-02-19 | 2011-08-25 | 덕산하이메탈(주) | Compound including indole derivative, organic electronic element using same, and terminal thereof |
Cited By (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9533954B2 (en) | 2010-12-22 | 2017-01-03 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3 |
| US10213427B2 (en) | 2010-12-22 | 2019-02-26 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3 |
| US10813930B2 (en) | 2010-12-22 | 2020-10-27 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3 |
| US11053246B2 (en) | 2012-06-13 | 2021-07-06 | Incyte Corporation | Substituted tricyclic compounds as FGFR inhibitors |
| US10131667B2 (en) | 2012-06-13 | 2018-11-20 | Incyte Corporation | Substituted tricyclic compounds as FGFR inhibitors |
| US11840534B2 (en) | 2012-06-13 | 2023-12-12 | Incyte Corporation | Substituted tricyclic compounds as FGFR inhibitors |
| US9611267B2 (en) | 2012-06-13 | 2017-04-04 | Incyte Holdings Corporation | Substituted tricyclic compounds as FGFR inhibitors |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| US9745311B2 (en) | 2012-08-10 | 2017-08-29 | Incyte Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| WO2014030921A1 (en) * | 2012-08-21 | 2014-02-27 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescence compounds and organic electroluminescence device containing the same |
| US9748492B2 (en) | 2012-11-02 | 2017-08-29 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
| US10388885B2 (en) | 2012-11-02 | 2019-08-20 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
| WO2014088352A1 (en) * | 2012-12-06 | 2014-06-12 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| US9533984B2 (en) | 2013-04-19 | 2017-01-03 | Incyte Holdings Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US10450313B2 (en) | 2013-04-19 | 2019-10-22 | Incyte Holdings Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US11530214B2 (en) | 2013-04-19 | 2022-12-20 | Incyte Holdings Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US10947230B2 (en) | 2013-04-19 | 2021-03-16 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US10040790B2 (en) | 2013-04-19 | 2018-08-07 | Incyte Holdings Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US20140374711A1 (en) * | 2013-06-14 | 2014-12-25 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US10158086B2 (en) * | 2013-06-14 | 2018-12-18 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US10411192B2 (en) | 2013-10-11 | 2019-09-10 | Idemitsu Kosan Co., Ltd. | Aromatic amine compound, organic electroluminescent element and electronic device |
| CN105529405A (en) * | 2014-10-17 | 2016-04-27 | 三星显示有限公司 | Organic light emitting component |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| US9966537B2 (en) | 2014-12-29 | 2018-05-08 | Dow Global Technologies Llc | Compositions with 2,3-disubstituted indoles as charge transport materials, and display devices fabricated therefrom |
| WO2016107459A1 (en) * | 2014-12-29 | 2016-07-07 | Dow Global Technologies Llc | Compositions with 2, 3-disubstituted indoles as charge transport materials, and display devices fabricated therefrom |
| WO2016126035A1 (en) * | 2015-02-03 | 2016-08-11 | 덕산네오룩스 주식회사 | Organic electronic element, and electronic device comprising same |
| US11667635B2 (en) | 2015-02-20 | 2023-06-06 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| US10738048B2 (en) | 2015-02-20 | 2020-08-11 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| US9801889B2 (en) | 2015-02-20 | 2017-10-31 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| US11173162B2 (en) | 2015-02-20 | 2021-11-16 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| US9708318B2 (en) | 2015-02-20 | 2017-07-18 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| US10016438B2 (en) | 2015-02-20 | 2018-07-10 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| US10632126B2 (en) | 2015-02-20 | 2020-04-28 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| US9890156B2 (en) | 2015-02-20 | 2018-02-13 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| US9580423B2 (en) | 2015-02-20 | 2017-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| US10251892B2 (en) | 2015-02-20 | 2019-04-09 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| US11014923B2 (en) | 2015-02-20 | 2021-05-25 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| US10214528B2 (en) | 2015-02-20 | 2019-02-26 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| US10611762B2 (en) | 2017-05-26 | 2020-04-07 | Incyte Corporation | Crystalline forms of a FGFR inhibitor and processes for preparing the same |
| CN108929261A (en) * | 2017-05-26 | 2018-12-04 | 东进世美肯株式会社 | Coating formation compound and organic luminescent device comprising it |
| US11472801B2 (en) | 2017-05-26 | 2022-10-18 | Incyte Corporation | Crystalline forms of a FGFR inhibitor and processes for preparing the same |
| CN108976162A (en) * | 2017-05-31 | 2018-12-11 | 东进世美肯株式会社 | Coating formation compound and organic luminescent device comprising it |
| CN109928950A (en) * | 2017-12-19 | 2019-06-25 | 三星显示有限公司 | Organnic electroluminescent device and amine compounds for Organnic electroluminescent device |
| EP3521280A1 (en) * | 2017-12-19 | 2019-08-07 | Samsung Display Co., Ltd | Organic electroluminescence device and amine compound for organic electroluminescence device |
| US11101442B2 (en) | 2017-12-19 | 2021-08-24 | Samsung Display Co., Ltd. | Organic electroluminescence device and amine compound for organic electroluminescence device |
| US11174257B2 (en) | 2018-05-04 | 2021-11-16 | Incyte Corporation | Salts of an FGFR inhibitor |
| US11466004B2 (en) | 2018-05-04 | 2022-10-11 | Incyte Corporation | Solid forms of an FGFR inhibitor and processes for preparing the same |
| US11628162B2 (en) | 2019-03-08 | 2023-04-18 | Incyte Corporation | Methods of treating cancer with an FGFR inhibitor |
| US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US11607416B2 (en) | 2019-10-14 | 2023-03-21 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US11566028B2 (en) | 2019-10-16 | 2023-01-31 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US11407750B2 (en) | 2019-12-04 | 2022-08-09 | Incyte Corporation | Derivatives of an FGFR inhibitor |
| US11897891B2 (en) | 2019-12-04 | 2024-02-13 | Incyte Corporation | Tricyclic heterocycles as FGFR inhibitors |
| CN112079767A (en) * | 2020-09-04 | 2020-12-15 | 江苏三月科技股份有限公司 | Aromatic amine compound and organic electroluminescent device comprising same |
| CN112079767B (en) * | 2020-09-04 | 2022-05-31 | 江苏三月科技股份有限公司 | Aromatic amine compound and organic electroluminescent device comprising same |
| CN114315693A (en) * | 2020-09-30 | 2022-04-12 | 江苏三月科技股份有限公司 | Arylamine compound and organic electroluminescent device comprising same |
| US11939331B2 (en) | 2021-06-09 | 2024-03-26 | Incyte Corporation | Tricyclic heterocycles as FGFR inhibitors |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2013109027A1 (en) | Compound, organic electronic element using same and electronic device thereof | |
| WO2017200320A1 (en) | Compound for organic electronic device, organic electronic device using same, and electronic apparatus thereof | |
| WO2017179875A1 (en) | Compound for organic electronic element, organic electronic element using same, and electronic device thereof | |
| WO2019231226A1 (en) | Compound for organic electric element, organic electric element using same, and electronic apparatus thereof | |
| WO2017204556A1 (en) | Compound for organic electronic element, organic electronic element using same and electronic device therefor | |
| WO2018012780A1 (en) | Compound for organic electric element, organic electric element using same, and electronic device comprising same organic electric element | |
| WO2017090918A1 (en) | Compound for organic electronic element, organic electronic element using same, and electronic device comprising same | |
| WO2017122978A1 (en) | Compound for organic electronic element, organic electronic element using same, and electronic device manufactured therewith | |
| WO2018021737A1 (en) | Compound for organic electronic element, organic electronic element using same, and electronic device thereof | |
| WO2016072691A1 (en) | Organic electronic device and display device using composition for organic electronic device | |
| WO2013105747A1 (en) | Compound for organic electronic element, organic electronic element using same and electronic device thereof | |
| WO2012177006A2 (en) | Compound for organic electronics, organic electronics using same, and electronic device for same | |
| WO2013081315A1 (en) | Compound for organic electronic device, organic electronic device comprising same and electronic device comprising the organic electronic device | |
| WO2016126022A1 (en) | Organic light-emitting element capable of low-voltage drive and having long life | |
| WO2015174682A1 (en) | Heterocyclic compound containing aromatic amine group, and organic light-emitting device comprising same | |
| WO2018026197A1 (en) | Compound for organic electric element, organic electric element using same, and electronic apparatus comprising same | |
| WO2018034517A1 (en) | Compound for organic electronic element, organic electronic element using same, and electronic device therefor | |
| WO2021112403A1 (en) | Organic electronic element comprising organic compound, and electronic device comprising same | |
| WO2017191976A1 (en) | Compound for organic electric element, organic electric element using same, and electronic device thereof | |
| WO2021025372A1 (en) | Organic electronic device | |
| WO2017188655A1 (en) | Compound for organic electric element, organic electric element using same, and electronic device comprising same organic electronic element | |
| WO2017160089A1 (en) | Compound for organic electric element, organic electric element using same, and electronic device therefrom | |
| WO2016129861A1 (en) | Novel compound for organic electric element, organic electric element using same, and electronic device comprising same | |
| WO2015190867A2 (en) | Compound for organic electronic element, organic electronic element using same, and electronic device thereof | |
| WO2021230651A1 (en) | Organic electronic element comprising compound for organic electronic element, and electronic device thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 13738262 Country of ref document: EP Kind code of ref document: A1 |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 14362883 Country of ref document: US |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 13738262 Country of ref document: EP Kind code of ref document: A1 |