KR20230076982A - Organic compound and electroluminescent device comprising the same - Google Patents
Organic compound and electroluminescent device comprising the same Download PDFInfo
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- KR20230076982A KR20230076982A KR1020210162963A KR20210162963A KR20230076982A KR 20230076982 A KR20230076982 A KR 20230076982A KR 1020210162963 A KR1020210162963 A KR 1020210162963A KR 20210162963 A KR20210162963 A KR 20210162963A KR 20230076982 A KR20230076982 A KR 20230076982A
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- 150000002894 organic compounds Chemical class 0.000 title description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 239000000126 substance Substances 0.000 claims abstract description 6
- 239000010410 layer Substances 0.000 claims description 65
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 239000012044 organic layer Substances 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 3
- 125000005104 aryl silyl group Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 229940125904 compound 1 Drugs 0.000 claims 1
- 230000003287 optical effect Effects 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 61
- 238000003786 synthesis reaction Methods 0.000 description 61
- 238000004519 manufacturing process Methods 0.000 description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 39
- 238000003756 stirring Methods 0.000 description 38
- 239000000463 material Substances 0.000 description 33
- -1 1 -Methylpentyl group Chemical group 0.000 description 28
- 239000000203 mixture Substances 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000000460 chlorine Substances 0.000 description 15
- 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 13
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 13
- 238000000605 extraction Methods 0.000 description 13
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 13
- 238000001953 recrystallisation Methods 0.000 description 13
- FNKCOUREFBNNHG-UHFFFAOYSA-N 1,3-dibromo-5-chlorobenzene Chemical compound ClC1=CC(Br)=CC(Br)=C1 FNKCOUREFBNNHG-UHFFFAOYSA-N 0.000 description 11
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 238000000151 deposition Methods 0.000 description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 239000010405 anode material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 3
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 3
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 3
- OIIOPWHTJZYKIL-PMACEKPBSA-N (5S)-5-[[[5-[2-chloro-3-[2-chloro-3-[6-methoxy-5-[[[(2S)-5-oxopyrrolidin-2-yl]methylamino]methyl]pyrazin-2-yl]phenyl]phenyl]-3-methoxypyrazin-2-yl]methylamino]methyl]pyrrolidin-2-one Chemical compound C1(=C(N=C(C2=C(C(C3=CC=CC(=C3Cl)C3=NC(OC)=C(N=C3)CNC[C@H]3NC(=O)CC3)=CC=C2)Cl)C=N1)OC)CNC[C@H]1NC(=O)CC1 OIIOPWHTJZYKIL-PMACEKPBSA-N 0.000 description 3
- 229940126657 Compound 17 Drugs 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 229940125936 compound 42 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- BPTABBGLHGBJQR-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 BPTABBGLHGBJQR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- 150000003852 triazoles Chemical group 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- HXITXNWTGFUOAU-RALIUCGRSA-N (2,3,4,5,6-pentadeuteriophenyl)boronic acid Chemical compound [2H]C1=C([2H])C([2H])=C(B(O)O)C([2H])=C1[2H] HXITXNWTGFUOAU-RALIUCGRSA-N 0.000 description 1
- DMDPAJOXRYGXCB-UHFFFAOYSA-N (9,9-dimethylfluoren-2-yl)boronic acid Chemical compound C1=C(B(O)O)C=C2C(C)(C)C3=CC=CC=C3C2=C1 DMDPAJOXRYGXCB-UHFFFAOYSA-N 0.000 description 1
- BBZVTTKMXRPMHZ-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoro-2-iodopropane Chemical compound FC(F)(F)C(F)(I)C(F)(F)F BBZVTTKMXRPMHZ-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical group C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- 150000000183 1,3-benzoxazoles Chemical class 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
- XHCAGOVGSDHHNP-UHFFFAOYSA-N 1-bromo-4-tert-butylbenzene Chemical compound CC(C)(C)C1=CC=C(Br)C=C1 XHCAGOVGSDHHNP-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- ALLIZEAXNXSFGD-UHFFFAOYSA-N 1-methyl-2-phenylbenzene Chemical group CC1=CC=CC=C1C1=CC=CC=C1 ALLIZEAXNXSFGD-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- SOQIDYYUSMPIDR-UHFFFAOYSA-N 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC=N1 SOQIDYYUSMPIDR-UHFFFAOYSA-N 0.000 description 1
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 1
- BZUUVQCSPHPUQA-UHFFFAOYSA-N 2-bromo-5-chloropyridine Chemical compound ClC1=CC=C(Br)N=C1 BZUUVQCSPHPUQA-UHFFFAOYSA-N 0.000 description 1
- NDDRCPBWWONGJR-UHFFFAOYSA-N 2-bromo-6-chloronaphthalene Chemical compound C1=C(Br)C=CC2=CC(Cl)=CC=C21 NDDRCPBWWONGJR-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-UHFFFAOYSA-N 0.000 description 1
- JTMODJXOTWYBOZ-UHFFFAOYSA-N 2-methyl-n-phenylaniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1 JTMODJXOTWYBOZ-UHFFFAOYSA-N 0.000 description 1
- 125000006607 3,3-dimethylbutyloxy group Chemical group 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical group CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- MQFYUZCANYLWEI-UHFFFAOYSA-N 4-methylnaphthalen-1-amine Chemical group C1=CC=C2C(C)=CC=C(N)C2=C1 MQFYUZCANYLWEI-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- QXDWMAODKPOTKK-UHFFFAOYSA-N 9-methylanthracen-1-amine Chemical group C1=CC(N)=C2C(C)=C(C=CC=C3)C3=CC2=C1 QXDWMAODKPOTKK-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- QPUNHNOEFWYAMU-UHFFFAOYSA-N FC(F)(F)C1=CC(C(F)(F)F)=CC(C=2C=CC(Br)=CC=2)=C1 Chemical group FC(F)(F)C1=CC(C(F)(F)F)=CC(C=2C=CC(Br)=CC=2)=C1 QPUNHNOEFWYAMU-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical group C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
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- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
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- 125000000304 alkynyl group Chemical group 0.000 description 1
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical group C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical group C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- 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 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
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- 229910052804 chromium Inorganic materials 0.000 description 1
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- 239000003086 colorant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
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- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical group C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
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- 239000010931 gold Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005241 heteroarylamino group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
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- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
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- 238000007641 inkjet printing Methods 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
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- 125000005921 isopentoxy group Chemical group 0.000 description 1
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- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006610 n-decyloxy group Chemical group 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000006609 n-nonyloxy group Chemical group 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
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- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 125000005484 neopentoxy group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
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- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
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- 229920000123 polythiophene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium 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
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
- C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
- C07C22/04—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
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Abstract
Description
본 발명은 유기발광소자에 구비되는 광효율 개선층 (Capping layer) 재료로 채용되는 것을 특징으로 하는 유기 화합물과 이를 채용하여 소자의 저전압 구동과 우수한 발광 효율 등의 발광 특성이 현저히 향상된 유기발광소자에 관한 것이다.The present invention relates to an organic light-emitting device characterized in that it is employed as a material for a capping layer provided in an organic light-emitting device, and an organic light-emitting device having significantly improved light-emitting characteristics such as low-voltage driving and excellent light-emitting efficiency by employing the organic compound. will be.
유기발광소자는 투명 기판 위에도 소자를 형성할 수 있을 뿐 아니라, 플라즈마 디스플레이 패널 (Plasma Display Panel)이나 무기전계발광 (EL) 디스플레이에 비해 10 V 이하의 저전압 구동이 가능하고, 전력 소모가 비교적 적으며, 색감이 뛰어나다는 장점이 있고, 녹색, 청색, 적색의 3가지 색을 나타낼 수가 있어 최근에 차세대 디스플레이 소자로 많은 관심의 대상이 되고 있다.Organic light emitting devices can not only be formed on a transparent substrate, but also can be driven at a low voltage of 10 V or less compared to plasma display panels or inorganic electroluminescent (EL) displays, and consume relatively little power. , It has the advantage of being excellent in color, and can show three colors of green, blue, and red, so it has recently become a subject of much interest as a next-generation display device.
다만, 이러한 유기발광소자가 상기와 같은 특징으로 발휘하기 위해서는 소자 내 유기층을 이루는 물질인 정공주입 물질, 정공수송 물질, 발광물질, 전자수송 물질, 전자주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지는 안정하고 효율적인 유기발광소자용 유기층 재료의 개발이 충분히 이루어지지 않은 상태이다.However, in order for the organic light emitting device to exhibit the above characteristics, the materials constituting the organic layer in the device, such as hole injection materials, hole transport materials, light emitting materials, electron transport materials, and electron injection materials, are supported by stable and efficient materials. However, the development of stable and efficient organic layer materials for organic light emitting devices has not yet been sufficiently accomplished.
따라서, 더욱 안정적인 유기발광소자를 구현하고, 소자의 고효율, 장수명, 대형화 등을 위해서는 효율 및 수명 특성 측면에서 추가적인 개선이 요구되고 있는 상황이고, 특히 유기발광소자의 각 유기층을 이루는 소재에 대한 개발이 절실히 필요한 실정이다.Therefore, in order to implement a more stable organic light emitting device, and to achieve high efficiency, long lifespan, and large size of the device, further improvement in terms of efficiency and lifespan characteristics is required, and in particular, development of materials forming each organic layer of the organic light emitting device is required. It is desperately needed.
또한, 최근에는 각 유기층 재료의 성능 변화를 주어 유기발광소자의 특성을 향상시키는 연구뿐만 아니라, 애노드 (anode)와 캐소드 (cathode) 사이에서 최적화된 광학 두께에 의한 색순도 향상 및 발광 효율 증대 기술이 소자 성능을 향상시키는데 중요한 요소 중의 하나로 착안되고 있으며, 이러한 방법의 일 예로 전극에 캡핑층 (capping layer)을 사용하여 광효율 증가와 우수한 색순도를 거두기도 한다.In addition, recently, research on improving the characteristics of an organic light emitting device by changing the performance of each organic layer material, as well as technology for improving color purity and increasing luminous efficiency by optimizing optical thickness between an anode and a cathode, has been conducted. It is considered as one of the important factors to improve performance, and as an example of this method, a capping layer is used on an electrode to increase light efficiency and achieve excellent color purity.
따라서, 본 발명은 유기발광소자에 구비되는 광효율 개선층 (capping layer)에 채용되어 소자의 저전압 구동과 향상된 발광 효율 등의 우수한 발광 특성을 구현할 수 있는 신규한 유기 화합물 및 이를 포함하는 유기발광소자를 제공하고자 한다.Therefore, the present invention provides a novel organic compound capable of realizing excellent light emitting characteristics such as low-voltage driving and improved luminous efficiency by being employed in a light efficiency improvement layer (capping layer) provided in an organic light emitting device and an organic light emitting device including the same. want to provide
본 발명은 상기 과제를 해결하기 위하여, 하기 [화학식 Ⅰ]로 표시되는 구조를 갖는 유기 화합물을 제공한다.In order to solve the above problems, the present invention provides an organic compound having a structure represented by the following [Chemical Formula I].
[화학식 Ⅰ][Formula I]
상기 [화학식 Ⅰ]의 특징적인 구조와 이에 의하여 구현되는 본 발명에 따른 구체적인 화합물, Ar1 내지 Ar2 및 L에 대해서는 후술하기로 한다.The characteristic structure of [Formula 1] and the specific compounds, Ar 1 to Ar 2 and L according to the present invention realized thereby will be described later.
또한, 본 발명은 제1 전극, 제2 전극, 및 상기 제1 전극과 제2 전극 사이에 배치된 1층 이상의 유기층을 포함하는 유기발광소자로서, 상기 제1 전극과 제2 전극의 상부 또는 하부 중에서 상기 유기층과 반대되는 적어도 일측에 형성되는 광효율 개선층 (Capping layer)을 더 포함하고, 상기 광효율 개선층은 상기 [화학식 Ⅰ]로 표시되는 유기 화합물을 포함하는 유기발광소자를 제공한다.In addition, the present invention is an organic light emitting device including a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein the upper or lower portions of the first electrode and the second electrode are provided. Further comprising a light efficiency improving layer (capping layer) formed on at least one side opposite to the organic layer, wherein the light efficiency improving layer provides an organic light emitting device including the organic compound represented by the [Chemical Formula I].
본 발명에 따른 유기 화합물은 유기발광소자에 구비되는 광효율 개선층 재료로 채용되어 유기발광소자의 저전압 구동과 우수한 발광 효율, 색순도 등의 향상된 발광 특성을 구현할 수 있어 조명 소자는 물론이고 다양한 디스플레이 소자에 유용하게 사용될 수 있다.The organic compound according to the present invention is employed as a light efficiency improvement layer material provided in an organic light emitting device, and can realize improved light emitting characteristics such as low voltage driving of the organic light emitting device, excellent light emitting efficiency, and color purity, and thus can be used in various display devices as well as lighting devices. can be useful
이하, 본 발명을 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명은 유기발광소자에 구비되는 광효율 개선층 재료로 채용되어 소자의 저전압 구동과 우수한 발광 효율, 색순도 등의 발광 특성을 거둘 수 있는 하기 [화학식 Ⅰ]로 표시되는 것을 특징으로 하는 유기 화합물에 관한 것이다.The present invention relates to an organic compound characterized in that it is represented by the following [Formula I], which is employed as a material for a light efficiency improvement layer provided in an organic light emitting device and can obtain light emitting characteristics such as low voltage driving of the device and excellent light emitting efficiency and color purity. will be.
[화학식 Ⅰ][Formula I]
상기 [화학식 Ⅰ]에서,In the above [Formula I],
L은 각각 독립적으로 직접 결합이거나, 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기 및 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴렌기 중에서 선택되고, n은 0 내지 3의 정수이며, 상기 n이 2 이상인 경우 복수 개의 L은 서로 동일하거나 상이하다.L is each independently a direct bond or is selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, n is an integer of 0 to 3, wherein n When is 2 or more, a plurality of L's are the same as or different from each other.
Ar1 및 Ar2는 서로 동일하거나 상이하며, 각각 독립적으로 중수소 (D), 시아노기 (CN), 할로겐기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 알콕시기, 치환 또는 비치환된 탄소수 1 내지 20의 할로겐화된 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 할로겐화된 알콕시기, 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 헤테로시클로알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴기 및 치환 또는 비치환된 아민기 중에서 선택된다.Ar 1 and Ar 2 are the same as or different from each other, and are each independently deuterium (D), a cyano group (CN), a halogen group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Alkoxy group, substituted or unsubstituted halogenated alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted halogenated alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and a substituted or unsubstituted amine group.
한편, 상기 L, Ar1 및 Ar2의 정의에서 '치환 또는 비치환된'이라 함은 상기 L, Ar1 및 Ar2가 각각 중수소, 할로겐기, 시아노기, 알킬기, 할로겐화된 알킬기, 중수소화된 알킬기, 시클로알킬기, 헤테로시클로알킬기, 알콕시기, 할로겐화된 알콕시기, 중수소화된 알콕시기, 아릴기, 헤테로아릴기, 알킬실릴기, 아릴실릴기 및 카르보닐기 중에서 선택된 1 또는 2 이상의 치환기로 치환되거나, 상기 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다.Meanwhile, 'substituted or unsubstituted' in the definition of L, Ar 1 and Ar 2 means that L, Ar 1 and Ar 2 are deuterium, halogen group, cyano group, alkyl group, halogenated alkyl group, deuterium, respectively. It is substituted with one or two or more substituents selected from an alkyl group, a cycloalkyl group, a heterocycloalkyl group, an alkoxy group, a halogenated alkoxy group, a deuterated alkoxy group, an aryl group, a heteroaryl group, an alkylsilyl group, an arylsilyl group, and a carbonyl group, It means that two or more substituents among the above substituents are substituted with linked substituents or do not have any substituents.
구체적인 예를 들면, 치환된 아릴기라 함은, 페닐기, 비페닐기, 나프탈렌기, 플루오레닐기, 파이레닐기, 페난트레닐기, 페릴렌기, 테트라세닐기, 안트라센닐기 등이 상기와 같은 치환기 등으로 치환된 것을 의미한다.For example, a substituted aryl group refers to a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetracenyl group, an anthracenyl group, etc. means it has been
또한, 치환된 헤테로아릴기라 함은, 피리딜기, 티오페닐기, 트리아진기, 퀴놀린기, 페난트롤린기, 이미다졸기, 티아졸기, 옥사졸기, 카바졸기 및 이들의 축합헤테로고리기, 예컨대 벤즈퀴놀린기, 벤즈이미다졸기, 벤즈옥사졸기, 벤즈티아졸기, 벤즈카바졸기, 디벤조티오페닐기, 디벤조퓨란기 등이 상기와 같은 치환기 등으로 치환된 것을 의미한다.In addition, the substituted heteroaryl group refers to a pyridyl group, a thiophenyl group, a triazine group, a quinoline group, a phenanthroline group, an imidazole group, a thiazole group, an oxazole group, a carbazole group, and condensed heterocyclic groups thereof, such as a benzquinoline group. , It means that a benzimidazole group, a benzoxazole group, a benzthiazole group, a benzcarbazole group, a dibenzothiophenyl group, a dibenzofuran group, etc. are substituted with the above substituents.
본 발명에 있어서, 상기 치환기들의 예시들에 대해서 아래에서 구체적으로 설명하나, 이에 한정되는 것은 아니다.In the present invention, examples of the substituents will be described in detail below, but are not limited thereto.
본 발명에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 구체적인 예로는 메틸기, 에틸기, 프로필기, n-프로필기, 이소프로필기, 부틸기, n-부틸기, 이소부틸기, tert-부틸기, sec-부틸기, 1-메틸-부틸기, 1-에틸-부틸기, 펜틸기, n-펜틸기, 이소펜틸기, 네오펜틸기, tert-펜틸기, 헥실기, n-헥실기, 1-메틸펜틸기, 2-메틸펜틸기, 4-메틸-2-펜틸기, 3,3-디메틸부틸기, 2-에틸부틸기, 헵틸기, n-헵틸기, 1-메틸헥실기, 시클로펜틸메틸기, 시클로헥틸메틸기, 옥틸기, n-옥틸기, tert-옥틸기, 1-메틸헵틸기, 2-에틸헥실기, 2-프로필펜틸기, n-노닐기, 2,2-디메틸헵틸기, 1-에틸-프로필기, 1,1-디메틸-프로필기, 이소헥실기, 2-메틸펜틸기, 4-메틸헥실기, 5-메틸헥실기 등이 있으나, 이들에 한정되지 않는다.In the present invention, the alkyl group may be a straight chain or branched chain, and specific examples include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group , sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1 -Methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentyl group methyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, etc., but is not limited thereto.
본 발명에 있어서, 알콕시기는 직쇄 또는 분지쇄일 수 있다. 구체적으로, 메톡시기, 에톡시기, n-프로폭시기, 이소프로폭시기, i-프로필옥시기, n-부톡시기, 이소부톡시기, tert-부톡시기, sec-부톡시기, n-펜틸옥시기, 네오펜틸옥시기, 이소펜틸옥시기, n-헥실옥시기, 3,3-디메틸부틸옥시기, 2-에틸부틸옥시기, n-옥틸옥시기, n-노닐옥시기, n-데실옥시기, 벤질옥시기, p-메틸벤질옥시기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present invention, the alkoxy group may be straight chain or branched chain. Specifically, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, i-propyloxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group , Neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group , benzyloxy group, p-methylbenzyloxy group, etc., but is not limited thereto.
본 발명에 있어서, 알킬기, 알콕시기는 중수소, 할로겐기 등으로 치환되어 중수소화된 알킬기 또는 알콕시기, 할로겐화된 알킬기 또는 알콕시기일 수 있다.In the present invention, the alkyl group or alkoxy group may be a deuterated alkyl group or alkoxy group, a halogenated alkyl group, or an alkoxy group substituted with deuterium or a halogen group.
본 발명에 있어서, 아릴기는 단환식 또는 다환식일 수 있고, 탄소수는 특별히 한정되지 않으나 6 내지 30인 것이 바람직하며, 또한 시클로알킬 등이 융합된 다환식 아릴기 구조를 포함하고, 단환식 아릴기의 예로는 페닐기, 비페닐기, 터페닐기, 스틸벤기 등이 있고, 다환식 아릴기의 예로는 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 테트라세닐기, 크라이세닐기, 플루오레닐기, 아세나프타센닐기, 트리페닐렌기, 플루오안트렌기 (fluoranthrene) 등이 있으나, 본 발명의 범위가 이들 예로만 한정되는 것은 아니다.In the present invention, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 30, and also includes a polycyclic aryl group structure in which cycloalkyl or the like is fused, and a monocyclic aryl group Examples of include a phenyl group, a biphenyl group, a terphenyl group, a stilbene group, and the like, and examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a tetracenyl group, and a chrysenyl group. , fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthrene group, etc., but the scope of the present invention is not limited only to these examples.
본 발명에 있어서, 플루오레닐기는 2개의 고리 유기화합물이 1개의 원자를 통하여 연결된 구조로서, 예로는 
본 발명에 있어서, 플루오레닐기는 열린 플루오레닐기의 구조를 포함하며, 여기서 열린 플루오레닐기는 2개의 고리 유기화합물이 1개의 원자를 통하여 연결된 구조에서 한쪽 고리 화합물의 연결이 끊어진 상태의 구조로서, 예로는 
또한, 상기 고리의 탄소원자는 N, S 및 O 중에서 선택되는 어느 하나 이상의 헤테로원자로 치환될 수 있으며, 예로는 
본 발명에 있어서, 헤테로아릴기는 이종원자로 O, N 또는 S를 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 3 내지 30인 것이 바람직하며, 시클로알킬 또는 헤테로시클로알킬 등이 융합된 다환식 헤테로아릴기 구조를 포함하며, 본 발명에서 이의 구체적인 예를 들면, 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 트리아졸기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 디벤조퓨라닐기, 페난트롤린기, 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기, 페녹사진기, 페노티아진기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present invention, the heteroaryl group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but preferably has 3 to 30 carbon atoms, and is a polycyclic group in which cycloalkyl or heterocycloalkyl is fused. It includes a heteroaryl group structure, and specific examples thereof in the present invention include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, and a bipyridyl group. , pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, Dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, phenoxazinyl group, phenothiazine group, etc., but only these It is not limited.
본 발명에 있어서, 아민기는 -NH2, 알킬아민기, 아릴아민기, 헤테로아릴아민기, 아릴헤테로아릴아민기 등일 수 있고, 아릴(헤테로아릴)아민기는 아릴기 및/또는 헤테로아릴기로 치환된 아민을 의미하고, 알킬아민기는 알킬로 치환된 아민을 의미하는 것이며, 아릴(헤테로아릴)아민기의 예로는 치환 또는 비치환된 모노 아릴(헤테로아릴)아민기, 치환 또는 비치환된 디 아릴(헤테로아릴)아민기, 또는 치환 또는 비치환된 트리 아릴(헤테로아릴)아민기가 있고, 상기 아릴(헤테로아릴)아민기 중의 아릴기와 헤테로아릴기는 상기 아릴기 및 헤테로아릴기의 정의와 동일하며, 상기 알킬아민기의 알킬기 역시 상기 알킬기의 정의와 동일하다.In the present invention, the amine group may be -NH 2 , an alkylamine group, an arylamine group, a heteroarylamine group, an arylheteroarylamine group, and the like, and the aryl (heteroaryl)amine group is substituted with an aryl group and/or a heteroaryl group. It means an amine, and the alkylamine group means an amine substituted with an alkyl, and examples of the aryl (heteroaryl) amine group include a substituted or unsubstituted mono aryl (heteroaryl) amine group, a substituted or unsubstituted diaryl ( There is a heteroaryl) amine group or a substituted or unsubstituted triaryl (heteroaryl) amine group, and the aryl group and the heteroaryl group in the aryl (heteroaryl) amine group are the same as the definitions of the aryl group and the heteroaryl group, and the above The alkyl group of the alkylamine group is also the same as the definition of the above alkyl group.
예시적으로 상기 아릴아민기로는 페닐아민기, 나프틸아민기, 비페닐아민기, 안트라세닐아민기, 3-메틸-페닐아민기, 4-메틸-나프틸아민기, 2-메틸-비페닐아민기, 9-메틸-안트라세닐아민기, 디페닐 아민기, 페닐나프틸아민기, 디톨릴아민기, 페닐톨릴아민기 및 트리페닐아민기 등이 있으나, 이에 한정되는 것은 아니다.Illustratively, the arylamine group includes a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 3-methyl-phenylamine group, a 4-methyl-naphthylamine group, and a 2-methyl-biphenyl group. amine group, 9-methyl-anthracenylamine group, diphenyl amine group, phenyl naphthylamine group, ditolylamine group, phenyltolylamine group and triphenylamine group, but are not limited thereto.
본 발명에 있어서, 실릴기는 비치환된 실릴기 또는 알킬기, 아릴기 등으로 치환된 알킬실릴기 또는 아릴실릴기로서, 이러한 실릴기의 구체적인 예로는 트리메틸실릴, 트리에틸실릴, 트리페닐실릴, 트리메톡시실릴, 디메톡시페닐실릴, 디페닐메틸실릴, 디페닐비닐실릴, 메틸사이클로뷰틸실릴, 디메틸퓨릴실릴 등을 들 수 있으며, 이에 한정되는 것은 아니다.In the present invention, the silyl group is an unsubstituted silyl group or an alkylsilyl group or an arylsilyl group substituted with an alkyl group or an aryl group, and specific examples of such a silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, and trimethylsilyl. and the like, but are not limited thereto.
본 발명에서 사용되는 치환기인 할로겐기의 구체적인 예로는 플루오르 (F), 클로린 (Cl), 브롬 (Br) 등을 들 수 있다.Specific examples of the substituent halogen group used in the present invention include fluorine (F), chlorine (Cl), and bromine (Br).
본 발명에 있어서, 시클로알킬기는 단환, 다환 및 스피로 알킬 라디칼을 지칭하고, 이를 포함하며, 바람직하게는 탄소수 3 내지 20의 고리 탄소 원자를 함유하는 것으로서, 시클로프로필, 시클로펜틸, 시클로헥실, 비시클로헵틸, 스피로데실, 스피로운데실, 아다만틸 등을 포함하며, 시클로알킬기는 임의로 치환될 수 있다.In the present invention, the cycloalkyl group refers to and includes monocyclic, polycyclic and spiroalkyl radicals, preferably containing ring carbon atoms of 3 to 20 carbon atoms, cyclopropyl, cyclopentyl, cyclohexyl, bicyclo heptyl, spirodecyl, spirundecyl, adamantyl, and the like, and the cycloalkyl group may be optionally substituted.
본 발명에 있어서, 헤테로시클로알킬기는 하나 이상의 헤테로 원자를 함유하는 방향족 및 비방향족 시클릭 라디칼을 지칭하고, 이를 포함하며, 하나 이상의 헤테로원자는 O, S, N, P, B, Si, 및 Se, 바람직하게는 O, N 또는 S로부터 선택되며, 구체적으로 N을 포함하는 경우 아지리딘, 피롤리딘, 피페리딘, 아제판, 아조칸 등일 수 있다.In the present invention, heterocycloalkyl groups refer to and include aromatic and non-aromatic cyclic radicals containing one or more heteroatoms, one or more heteroatoms being O, S, N, P, B, Si, and Se , Preferably selected from O, N or S, specifically, when N is included, it may be aziridine, pyrrolidine, piperidine, azepane, azocan, and the like.
본 발명에 있어서, 카르보닐기는 -COR'로 표시되는 것이며, 여기서 R'은 수소, 알킬기, 아릴기, 시클로알킬기, 알켄일기, 알킨일기, 또는 이들의 조합인 것이다.In the present invention, the carbonyl group is represented by -COR', where R' is hydrogen, an alkyl group, an aryl group, a cycloalkyl group, an alkenyl group, an alkynyl group, or a combination thereof.
상기 [화학식 Ⅰ]로 표시되는 본 발명에 따른 유기 화합물은 그 구조적 특이성으로 인하여 유기발광소자에 구비되는 광효율 개선층 (Capping layer) 재료로 사용될 수 있다.The organic compound according to the present invention represented by [Chemical Formula I] may be used as a material for a light efficiency improvement layer (capping layer) provided in an organic light emitting device due to its structural specificity.
본 발명에 따른 [화학식 Ⅰ]로 표시되는 유기 화합물의 바람직한 구체예로는 하기 화합물들이 있으나, 이들에만 한정되는 것은 아니다.Preferred specific examples of the organic compound represented by [Chemical Formula I] according to the present invention include the following compounds, but are not limited thereto.
이와 같이, 본 발명에 따른 유기 화합물은 고유의 특성을 갖는 모이어티 (moiety)를 이용하여 다양한 특성을 갖는 유기 화합물을 합성할 수 있고, 그 결과 본 발명에 따른 유기 화합물을 유기발광소자에 구비되는 광효율 개선층에 적용할 경우에 소자의 발광효율 등의 발광 특성을 더욱 향상시킬 수 있다.As described above, the organic compound according to the present invention can synthesize organic compounds having various characteristics by using a moiety having intrinsic characteristics, and as a result, the organic compound according to the present invention is provided in an organic light emitting device. When applied to the light efficiency improving layer, light emitting characteristics such as light emitting efficiency of the device can be further improved.
또한, 본 발명의 화합물은 일반적인 유기발광소자 제조방법에 따라 소자에 적용할 수 있으며, 본 발명의 일 실시예에 따른 유기발광소자는 제1 전극과 제2 전극 및 이 사이에 배치된 유기층을 포함하는 구조로 이루어질 수 있으며, 본 발명에 따른 유기발광 화합물을 소자의 유기층에 사용한다는 것을 제외하고는 통상의 소자 제조방법 및 재료를 사용하여 제조될 수 있다.In addition, the compound of the present invention can be applied to a device according to a general organic light emitting device manufacturing method, and an organic light emitting device according to an embodiment of the present invention includes a first electrode and a second electrode and an organic layer disposed therebetween. It can be made of a structure, and can be manufactured using conventional device manufacturing methods and materials, except that the organic light emitting compound according to the present invention is used in the organic layer of the device.
본 발명에 따른 유기발광소자의 유기층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층, 전자저지층, 정공저지층, 광효율 개선층 (Capping layer) 등을 포함하는 구조를 가질 수 있다. 그러나, 이에 한정되지 않고 더 적은 수, 더 많은 수의 유기층을 포함할 수도 있다.The organic layer of the organic light emitting device according to the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, a light efficiency improvement layer (capping layer), and the like. However, it is not limited thereto and may include fewer or more organic layers.
본 발명의 일 실시예에 따른 유기전기발광소자는 기판, 제1 전극 (양극), 유기층, 제2 전극 (음극) 및 광효율 개선층을 포함하며, 상기 광효율 개선층은 제1 전극 하부 (Bottom emission) 또는 제2 전극 상부 (Top emission)에 형성될 수 있다.An organic light emitting device according to an embodiment of the present invention includes a substrate, a first electrode (anode), an organic layer, a second electrode (cathode), and a light efficiency improvement layer, wherein the light efficiency improvement layer is a bottom emission layer of the first electrode. ) or on top of the second electrode (top emission).
제2 전극 상부 (Top emission)에 형성되는 방식은 발광층에서 형성된 빛이 캐소드쪽으로 방출되는데 캐소드쪽으로 방출되는 빛이 굴절률이 상대적으로 높은 본 발명에 따른 화합물로 형성된 광효율 개선층 (CPL)을 통과하면서 빛의 파장이 증폭되고 따라서 광효율이 상승하게 된다.In the method formed on the second electrode (top emission), the light formed in the light emitting layer is emitted toward the cathode, and the light emitted toward the cathode passes through the light efficiency improving layer (CPL) formed of the compound according to the present invention having a relatively high refractive index. The wavelength of the light is amplified and thus the light efficiency is increased.
본 발명에 따른 바람직한 유기발광소자의 유기층 구조 등에 대해서는 후술하는 실시예에서 보다 상세하게 설명한다.An organic layer structure of a preferred organic light emitting device according to the present invention will be described in more detail in Examples to be described later.
또한, 본 발명에 따른 유기발광소자는 스퍼터링 (sputtering)이나 전자빔 증발 (e-beam evaporation)과 같은 PVD (physical vapor deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층, 전자 수송층을 포함하는 유기층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다.In addition, the organic light emitting device according to the present invention uses a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal or conductive metal oxide or an alloy thereof on a substrate. It can be manufactured by depositing an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기층, 양극 물질을 차례로 증착시켜 유기발광소자를 만들 수도 있다. 상기 유기층은 정공 주입층, 정공 수송층, 발광층 및 전자 수송층 등을 포함하는 다층 구조일 수도 있으나, 이에 한정되지 않고 단층 구조일 수 있다. 또한, 상기 유기층은 다양한 고분자 소재를 사용하여 증착법이 아닌 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.In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate. The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic layer can be formed by using various polymer materials and using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. Can be made in layers.
상기 양극 물질로는 통상 유기층으로 정공주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금, 아연 산화물, 인듐 산화물, 인듐 주석 산화물 (ITO), 인듐 아연 산화물 (IZO)과 같은 금속 산화물, ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜 ] (PEDT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.As the anode material, a material having a high work function is generally preferred so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO). Metal oxides, combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT) , but conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.
상기 음극 물질로는 통상 유기층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금, LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다.The cathode material is preferably a material having a small work function so as to easily inject electrons into the organic layer. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof, and multilayers such as LiF/Al or LiO 2 /Al. structural materials, etc., but are not limited thereto.
정공주입 물질로는 낮은 전압에서 양극으로부터 정공을 잘 주입받을 수 있는 물질로서, 정공주입 물질의 HOMO (highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기층의 HOMO 사이인 것이 바람직하다. 정공주입 물질의 구체적인 예로는 금속 포피린 (porphyrine), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴 헥사아자트리페닐렌, 퀴나크리돈 (quinacridone) 계열의 유기물, 페릴렌 (perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.The hole injection material is a material capable of injecting holes well from the anode at a low voltage, and the hole injection material preferably has a highest occupied molecular orbital (HOMO) between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, Anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.
정공수송 물질로는 양극이나 정공주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다.As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high hole mobility is suitable. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.
발광 물질로는 정공수송층과 전자수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물 (Alq3), 카르바졸 계열 화합물, 이량체화 스티릴 (dimerized styryl) 화합물, BAlq, 10-히드록시벤조 퀴놀린-금속 화합물, 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물, 폴리(p-페닐렌비닐렌) (PPV) 계열의 고분자, 스피로 (spiro) 화합물, 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazoles, benzthiazoles, and Examples include benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, and rubrene, but are not limited thereto.
전자수송 물질로는 음극으로부터 전자를 잘 주입받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물, Alq3를 포함한 착물, 유기 라디칼 화합물, 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다.As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is suitable. Specific examples include an Al complex of 8-hydroxyquinoline, a complex including Alq 3 , an organic radical compound, and a hydroxyflavone-metal complex, but are not limited thereto.
본 발명에 따른 유기발광소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a double side emission type depending on the material used.
또한, 본 발명에 따른 유기발광 화합물은 유기 태양 전지, 유기 감광체, 유기 트랜지스터 등을 비롯한 유기 전자 소자에서도 유기발광소자에 적용되는 것과 유사한 원리로 작용할 수 있다.In addition, the organic light emitting compound according to the present invention may act in organic electronic devices including organic solar cells, organic photoreceptors, organic transistors, and the like, on a principle similar to that applied to organic light emitting devices.
이하, 바람직한 실시예를 들어 본 발명을 더욱 상세하게 설명한다. 그러나, 이들 실시예는 본 발명을 보다 구체적으로 설명하기 위한 것으로, 본 발명의 범위가 이에 의하여 제한되지 않고, 본 발명의 범주 및 기술사상 범위 내에서 다양한 변경 및 수정이 가능함은 당업계의 통상의 지식을 가진 자에게 자명할 것이다.Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are intended to explain the present invention in more detail, and the scope of the present invention is not limited thereto, and various changes and modifications are possible within the scope and spirit of the present invention. It will be self-evident to those who have knowledge.
합성예synthesis example 1 : 화합물 7의 합성 1: Synthesis of Compound 7
(1) (One) 제조예manufacturing example 1 : 중간체 7-1의 합성 1: synthesis of intermediate 7-1
1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), Heptafluoro-2-iodopropane (32.9 g, 0.111 mol), Cu (18.8 g, 0.296 mol), DMF 30 mL를 넣고, 질소 조건에서 24시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 7-1>을 7.6 g (수율 45.8%) 수득하였다.1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), Heptafluoro-2-iodopropane (32.9 g, 0.111 mol), Cu (18.8 g, 0.296 mol), and 30 mL of DMF were added and stirred for 24 hours under nitrogen conditions. While stirring at 100 ℃ was reacted. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 7.6 g of <Intermediate 7-1> (yield: 45.8%).
(2) (2) 제조예manufacturing example 2 : 중간체 7-2의 합성 2: synthesis of intermediate 7-2
1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), Phenyl-D5-boronic acid (11.3 g, 0.089 mol), K2CO3 (30.7 g, 0.222 mol), Pd(PPh3)4 (0.9 g, 0.74 mmol)에 Toluene 200 mL, EtOH 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 7-2>를 7.3 g (수율 71.8%) 수득하였다.1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), Phenyl-D5-boronic acid (11.3 g, 0.089 mol), K 2 CO 3 (30.7 g, 0.222 mol), Pd(PPh 3 ) 4 ( 0.9 g, 0.74 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H 2 O, and reacted by stirring at 80 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 7.3 g of <Intermediate 7-2> (yield: 71.8%).
(3) (3) 제조예manufacturing example 3 : 중간체 7-3의 합성 3: synthesis of intermediate 7-3
중간체 7-2 (10.0 g, 0.036 mol), Bis(pinacolato)diboron (25.0 g, 0.043 mol), KOAc (7.1 g, 0.072 mol), Pd(dppf)Cl2 (0.8 g, 1.08 mmol), X-Phos (0.6 g, 1.29 mmol)에 Dioxane 200 mL를 넣고 12시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 7-3>을 9.1 g (수율 68.3%) 수득하였다.Intermediate 7-2 (10.0 g, 0.036 mol), Bis(pinacolato)diboron (25.0 g, 0.043 mol), KOAc (7.1 g, 0.072 mol), Pd(dppf)Cl 2 (0.8 g, 1.08 mmol), X- Dioxane (200 mL) was added to Phos (0.6 g, 1.29 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 9.1 g (yield 68.3%) of <Intermediate 7-3> was obtained by extraction and concentration, followed by column and recrystallization.
(4) (4) 제조예manufacturing example 4 : 화합물 7의 합성 4: synthesis of compound 7
중간체 7-1 (10.0 g, 0.022 mol), 중간체 7-3 (9.8 g, 0.027 mol), K2CO3 (9.2 g, 0.066 mol), Pd(OAc)2 (1.3 g, 1.1 mmol), X-Phos (1.1 g, 2.2 mmol), THF 200 mL와 H2O 50 mL를 넣고 6시간 동안 90 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 7>을 10.3 g (수율 70.8%) 수득하였다.Intermediate 7-1 (10.0 g, 0.022 mol), Intermediate 7-3 (9.8 g, 0.027 mol), K 2 CO 3 (9.2 g, 0.066 mol), Pd(OAc) 2 (1.3 g, 1.1 mmol), X -Phos (1.1 g, 2.2 mmol), 200 mL of THF and 50 mL of H 2 O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 10.3 g of <Compound 7> (yield: 70.8%).
LC/MS: m/z=652[(M)+]LC/MS: m/z = 652 [(M) + ]
합성예synthesis example 2 : 화합물 17의 합성 2: synthesis of compound 17
(1) (One) 제조예manufacturing example 1 : 중간체 17-1의 합성 1: synthesis of intermediate 17-1
1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), 3,5-Bis(tert-butyl)phenyl-pinacolatoboronate (28.1 g, 0.089 mol), K2CO3 (30.7 g, 0.222 mol), Pd(PPh3)4 (0.9 g, 0.74 mmol)에 Toluene 200 mL, EtOH 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 7-1>을 13.8 g (수율 76.3%) 수득하였다.1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), 3,5-Bis(tert-butyl)phenyl-pinacolatoboronate (28.1 g, 0.089 mol), K 2 CO 3 (30.7 g, 0.222 mol), 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H 2 O were added to Pd(PPh 3 ) 4 (0.9 g, 0.74 mmol), followed by stirring at 80 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 13.8 g of <Intermediate 7-1> (yield: 76.3%).
(2) (2) 제조예manufacturing example 2 : 중간체 17-2의 합성 2: synthesis of intermediate 17-2
중간체 17-1 (10.0 g, 0.020 mol), Bis(pinacolato)diboron (14.1 g, 0.024 mol), KOAc (4.0 g, 0.040 mol), Pd(dppf)Cl2 (0.5 g, 0.6 mmol), X-Phos (0.4 g, 0.72 mmol)에 Dioxane 200 mL를 넣고 12시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 17-2>를 8.4 g (수율 70.8%) 수득하였다.Intermediate 17-1 (10.0 g, 0.020 mol), Bis(pinacolato)diboron (14.1 g, 0.024 mol), KOAc (4.0 g, 0.040 mol), Pd(dppf)Cl 2 (0.5 g, 0.6 mmol), X- Dioxane (200 mL) was added to Phos (0.4 g, 0.72 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 8.4 g (yield 70.8%) of <Intermediate 17-2> was obtained by extraction and concentration, followed by column and recrystallization.
(3) (3) 제조예manufacturing example 3 : 화합물 17의 합성 3: Synthesis of Compound 17
중간체 7-1 (10.0 g, 0.022 mol), 중간체 17-2 (15.5 g, 0.026 mol), K2CO3 (9.2 g, 0.066 mol), Pd(OAc)2 (1.3 g, 1.1 mmol), X-Phos (1.1 g, 2.2 mmol), THF 200 mL와 H2O 50 mL를 넣고 6시간 동안 90 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 17>을 12.5 g (수율 64.7%) 수득하였다.Intermediate 7-1 (10.0 g, 0.022 mol), Intermediate 17-2 (15.5 g, 0.026 mol), K 2 CO 3 (9.2 g, 0.066 mol), Pd(OAc) 2 (1.3 g, 1.1 mmol), X -Phos (1.1 g, 2.2 mmol), 200 mL of THF and 50 mL of H 2 O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted and concentrated, and then column and recrystallized to obtain 12.5 g of <Compound 17> (yield: 64.7%).
LC/MS: m/z=866[(M)+]LC/MS: m/z=866 [(M) + ]
합성예synthesis example 3 : 화합물 19의 합성 3: synthesis of compound 19
(1) (One) 제조예manufacturing example 1 : 중간체 19-1의 합성 1: synthesis of intermediate 19-1
1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), 3,5-Bis(trifluoromethyl)phenylboronic acid (22.9 g, 0.089 mol), K2CO3 (30.7 g, 0.222 mol), Pd(PPh3)4 (0.9 g, 0.74 mmol)에 Toluene 200 mL, EtOH 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 19-1>을 15.4 g (수율 77.6%) 수득하였다.1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), 3,5-Bis(trifluoromethyl)phenylboronic acid (22.9 g, 0.089 mol), K 2 CO 3 (30.7 g, 0.222 mol), Pd (PPh) 3 ) 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H 2 O were added to 4 (0.9 g, 0.74 mmol), followed by stirring at 80 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 15.4 g of <Intermediate 19-1> (yield: 77.6%).
(2) (2) 제조예manufacturing example 2 : 중간체 19-2의 합성 2: synthesis of intermediate 19-2
중간체 19-1 (10.0 g, 0.019 mol), Bis(pinacolato)diboron (12.8 g, 0.023 mol), KOAc (3.7 g, 0.038 mol), Pd(dppf)Cl2 (0.4 g, 0.57 mmol), X-Phos (0.3 g, 0.69 mmol)에 Dioxane 200 mL를 넣고 12시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 19-2>를 7.9 g (수율 67.5%) 수득하였다.Intermediate 19-1 (10.0 g, 0.019 mol), Bis(pinacolato)diboron (12.8 g, 0.023 mol), KOAc (3.7 g, 0.038 mol), Pd(dppf)Cl 2 (0.4 g, 0.57 mmol), X- Dioxane (200 mL) was added to Phos (0.3 g, 0.69 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 7.9 g (yield 67.5%) of <Intermediate 19-2> was obtained by extraction and concentration, followed by column and recrystallization.
(3) (3) 제조예manufacturing example 3 : 화합물 19의 합성 3: synthesis of compound 19
중간체 7-1 (10.0 g, 0.022 mol), 중간체 19-2 (16.8 g, 0.026 mol), K2CO3 (9.2 g, 0.066 mol), Pd(OAc)2 (1.3 g, 1.1 mmol), X-Phos (1.1 g, 2.2 mmol), THF 200 mL와 H2O 50 mL를 넣고 6시간 동안 90 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 19>를 14.7 g (수율 72.1%) 수득하였다.Intermediate 7-1 (10.0 g, 0.022 mol), Intermediate 19-2 (16.8 g, 0.026 mol), K 2 CO 3 (9.2 g, 0.066 mol), Pd(OAc) 2 (1.3 g, 1.1 mmol), X -Phos (1.1 g, 2.2 mmol), 200 mL of THF and 50 mL of H 2 O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 14.7 g of <Compound 19> (yield: 72.1%).
LC/MS: m/z=914(M)+]LC/MS: m/z=914(M) + ]
합성예synthesis example 4 : 화합물 34의 합성 4: synthesis of compound 34
(1) (One) 제조예manufacturing example 1 : 중간체 34-1의 합성 1: synthesis of intermediate 34-1
4'-Bromo-3,5-Bis(Trifluoromethyl)-1,1'-Biphenyl (10.0 g, 0.027 mol), Bis(pinacolato)diboron (8.3 g, 0.032 mol), KOAc (8.0 g, 0.081 mol), Pd(dppf)Cl2 (1.0 g, 1.35 mmol)에 Dioxane 200 mL를 넣고 12시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 34-1>을 8.6 g (수율 76.3%) 수득하였다.4'-Bromo-3,5-Bis(Trifluoromethyl)-1,1'-Biphenyl (10.0 g, 0.027 mol), Bis(pinacolato)diboron (8.3 g, 0.032 mol), KOAc (8.0 g, 0.081 mol), 200 mL of Dioxane was added to Pd(dppf)Cl 2 (1.0 g, 1.35 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 8.6 g of <Intermediate 34-1> (yield: 76.3%).
(2) (2) 제조예manufacturing example 2 : 중간체 34-2의 합성 2: synthesis of intermediate 34-2
1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), 중간체 34-1 (36.9 g, 0.089 mol), K2CO3 (30.7 g, 0.222 mol), Pd(PPh3)4 (0.9 g, 0.74 mmol)에 Toluene 200 mL, EtOH 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 34-2>를 18.2 g (수율 71.4%) 수득하였다.1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), intermediate 34-1 (36.9 g, 0.089 mol), K 2 CO 3 (30.7 g, 0.222 mol), Pd(PPh 3 ) 4 (0.9 g , 0.74 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H 2 O, and reacted by stirring at 80 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 18.2 g of <Intermediate 34-2> (yield: 71.4%).
(3) (3) 제조예manufacturing example 3 : 중간체 34-3의 합성 3: synthesis of intermediate 34-3
중간체 34-2 (10.0 g, 0.015 mol), Bis(pinacolato)diboron (10.0 g, 0.018 mol), KOAc (2.9 g, 0.030 mol), Pd(dppf)Cl2 (0.3 g, 0.45 mmol), X-Phos (0.3 g, 0.54 mmol)에 Dioxane 200 mL를 넣고 12시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 34-3>을 7.4 g (수율 65.3%) 수득하였다.Intermediate 34-2 (10.0 g, 0.015 mol), Bis(pinacolato)diboron (10.0 g, 0.018 mol), KOAc (2.9 g, 0.030 mol), Pd(dppf)Cl 2 (0.3 g, 0.45 mmol), X- 200 mL of Dioxane was added to Phos (0.3 g, 0.54 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 7.4 g (yield 65.3%) of <Intermediate 34-3> was obtained by extraction, concentration, column and recrystallization.
(4) (4) 제조예manufacturing example 4 : 화합물 34의 합성 4: synthesis of compound 34
중간체 7-1 (10.0 g, 0.022 mol), 중간체 34-3 (20.9 g, 0.026 mol), K2CO3 (9.2 g, 0.066 mol), Pd(OAc)2 (1.3 g, 1.1 mmol), X-Phos (1.1 g, 2.2 mmol), THF 200 mL와 H2O 50 mL를 넣고 6시간 동안 90 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 34>를 16.8 g (수율 70.7%) 수득하였다.Intermediate 7-1 (10.0 g, 0.022 mol), Intermediate 34-3 (20.9 g, 0.026 mol), K 2 CO 3 (9.2 g, 0.066 mol), Pd(OAc) 2 (1.3 g, 1.1 mmol), X -Phos (1.1 g, 2.2 mmol), 200 mL of THF and 50 mL of H 2 O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 16.8 g of <Compound 34> (yield: 70.7%).
LC/MS: m/z=1066(M)+]LC/MS: m/z=1066(M) + ]
합성예synthesis example 5 : 화합물 42의 합성 5: Synthesis of Compound 42
(1) (One) 제조예manufacturing example 1 : 중간체 42-1의 합성 1: synthesis of intermediate 42-1
1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), 2-Pyrrolidinone (7.6 g, 0.089 mol), K3PO4 (33.7 g, 0.104 mol), Pd(dba)2 (2.1 g, 3.7 mmol), Xant-Phos (15.4 g, 0.027 mol), Dioxane을 넣고 16시간 동안 환류 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 42-1>을 8.3 g (수율 80.5%) 수득하였다.1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), 2-Pyrrolidinone (7.6 g, 0.089 mol), K 3 PO 4 (33.7 g, 0.104 mol), Pd(dba) 2 (2.1 g, 3.7 mmol), Xant-Phos (15.4 g, 0.027 mol), and dioxane were added and stirred under reflux for 16 hours to react. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 8.3 g of <Intermediate 42-1> (yield: 80.5%).
(2) (2) 제조예manufacturing example 2 : 중간체 42-2의 합성 2: synthesis of intermediate 42-2
중간체 42-1 (10.0 g, 0.036 mol), Bis(pinacolato)diboron (24.7 g, 0.043 mol), KOAc (7.0 g, 0.072 mol), Pd(dppf)Cl2 (0.8 g, 1.08 mmol), X-Phos (0.6 g, 1.29 mmol)에 Dioxane 200 mL를 넣고 12시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 42-2>를 9.1 g (수율 68.5%) 수득하였다.Intermediate 42-1 (10.0 g, 0.036 mol), Bis(pinacolato)diboron (24.7 g, 0.043 mol), KOAc (7.0 g, 0.072 mol), Pd(dppf)Cl 2 (0.8 g, 1.08 mmol), X- Dioxane (200 mL) was added to Phos (0.6 g, 1.29 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, after extraction and concentration, 9.1 g (yield 68.5%) of <Intermediate 42-2> was obtained by column.
(3) (3) 제조예manufacturing example 3 : 중간체 42-3의 합성 3: synthesis of intermediate 42-3
1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), 중간체 42-2 (32.9 g, 0.089 mol), K2CO3 (30.7 g, 0.222 mol), Pd(PPh3)4 (0.9 g, 0.74 mmol)에 Toluene 200 mL, EtOH 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 42-3>을 17.4 g (수율 78.8%) 수득하였다.1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), intermediate 42-2 (32.9 g, 0.089 mol), K 2 CO 3 (30.7 g, 0.222 mol), Pd(PPh 3 ) 4 (0.9 g , 0.74 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H 2 O, and reacted by stirring at 80 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 17.4 g of <Intermediate 42-3> (yield: 78.8%).
(4) (4) 제조예manufacturing example 4 : 중간체 42-4의 합성 4: synthesis of intermediate 42-4
중간체 42-3 (10.0 g, 0.017 mol), Bis(pinacolato)diboron (11.5 g, 0.020 mol), KOAc (3.3 g, 0.034 mol), Pd(dppf)Cl2 (0.4 g, 0.51 mmol), X-Phos (0.3 g, 0.6 mmol)에 Dioxane 200 mL를 넣고 12시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 42-4>를 8.2 g (수율 71.1%) 수득하였다.Intermediate 42-3 (10.0 g, 0.017 mol), Bis(pinacolato)diboron (11.5 g, 0.020 mol), KOAc (3.3 g, 0.034 mol), Pd(dppf)Cl 2 (0.4 g, 0.51 mmol), X- Dioxane (200 mL) was added to Phos (0.3 g, 0.6 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 8.2 g (yield 71.1%) of <Intermediate 42-4> was obtained by extraction and concentration, followed by column and recrystallization.
(5) (5) 제조예manufacturing example 5 : 화합물 42의 합성 5: Synthesis of Compound 42
중간체 7-1 (10.0 g, 0.022 mol), 중간체 42-4 (18.4 g, 0.026 mol), K2CO3 (9.2 g, 0.066 mol), Pd(OAc)2 (1.3 g, 1.1 mmol), X-Phos (1.1 g, 2.2 mmol), THF 200 mL와 H2O 50 mL를 넣고 6시간 동안 90 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 42>를 14.3 g (수율 65.8%) 수득하였다.Intermediate 7-1 (10.0 g, 0.022 mol), Intermediate 42-4 (18.4 g, 0.026 mol), K 2 CO 3 (9.2 g, 0.066 mol), Pd(OAc) 2 (1.3 g, 1.1 mmol), X -Phos (1.1 g, 2.2 mmol), 200 mL of THF and 50 mL of H 2 O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted and concentrated, followed by column and recrystallization to obtain 14.3 g of <Compound 42> (yield: 65.8%).
LC/MS: m/z=1974(M)+]LC/MS: m/z=1974(M) + ]
합성예synthesis example 6 : 화합물 52의 합성 6: synthesis of compound 52
(1) (One) 제조예manufacturing example 1 : 중간체 52-1의 합성 1: synthesis of intermediate 52-1
1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), 5-(2-Trfluoromethylphenyl)pyridine-2-boronic acid pinacol ester (31.0 g, 0.089 mol), K2CO3 (30.7 g, 0.222 mol), Pd(PPh3)4 (0.9 g, 0.74 mmol)에 Toluene 200 mL, EtOH 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 52-1>을 15.1 g (수율 73.6%) 수득하였다.1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), 5-(2-Trfluoromethylphenyl)pyridine-2-boronic acid pinacol ester (31.0 g, 0.089 mol), K 2 CO 3 (30.7 g, 0.222 mol) ) and Pd(PPh 3 ) 4 (0.9 g, 0.74 mmol), 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H 2 O were added and reacted by stirring at 80 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 15.1 g of <Intermediate 52-1> (yield: 73.6%).
(2) (2) 제조예manufacturing example 2 : 중간체 52-2의 합성 2: synthesis of intermediate 52-2
중간체 52-1 (10.0 g, 0.018 mol), Bis(pinacolato)diboron (12.4 g, 0.022 mol), KOAc (3.5 g, 0.036 mol), Pd(dppf)Cl2 (0.4 g, 0.54 mmol), X-Phos (0.3 g, 0.66 mmol)에 Dioxane 200 mL를 넣고 12시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 52-2>를 7.1 g (수율 61.0%) 수득하였다.Intermediate 52-1 (10.0 g, 0.018 mol), Bis(pinacolato)diboron (12.4 g, 0.022 mol), KOAc (3.5 g, 0.036 mol), Pd(dppf)Cl 2 (0.4 g, 0.54 mmol), X- Dioxane (200 mL) was added to Phos (0.3 g, 0.66 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 7.1 g (yield: 61.0%) of <Intermediate 52-2> was obtained by extraction and concentration, followed by column and recrystallization.
(3) (3) 제조예manufacturing example 3 : 화합물 52의 합성 3: Synthesis of Compound 52
중간체 7-1 (10.0 g, 0.022 mol), 중간체 52-2 (17.3 g, 0.026 mol), K2CO3 (9.2 g, 0.066 mol), Pd(OAc)2 (1.3 g, 1.1 mmol), X-Phos (1.1 g, 2.2 mmol), THF 200 mL와 H2O 50 mL를 넣고 6시간 동안 90 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 52>를 14.3 g (수율 68.8%) 수득하였다.Intermediate 7-1 (10.0 g, 0.022 mol), Intermediate 52-2 (17.3 g, 0.026 mol), K 2 CO 3 (9.2 g, 0.066 mol), Pd(OAc) 2 (1.3 g, 1.1 mmol), X -Phos (1.1 g, 2.2 mmol), 200 mL of THF and 50 mL of H 2 O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 14.3 g of <Compound 52> (yield: 68.8%).
LC/MS: m/z=932(M)+]LC/MS: m/z=932(M) + ]
합성예synthesis example 7 : 화합물 105의 합성 7: synthesis of compound 105
(1) (One) 제조예manufacturing example 1 : 중간체 105-1의 합성 1: synthesis of intermediate 105-1
중간체 7-1 (10.0 g, 0.022 mol), Bis(pinacolato)diboron (15.3 g, 0.026 mol), KOAc (4.4 g, 0.044 mol), Pd(dppf)Cl2 (0.5 g, 0.66 mmol), X-Phos (0.4 g, 0.78 mmol)에 Dioxane 200 mL를 넣고 12시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 105-1>을 8.6 g (수율 71.4%) 수득하였다.Intermediate 7-1 (10.0 g, 0.022 mol), Bis(pinacolato)diboron (15.3 g, 0.026 mol), KOAc (4.4 g, 0.044 mol), Pd(dppf)Cl 2 (0.5 g, 0.66 mmol), X- Dioxane (200 mL) was added to Phos (0.4 g, 0.78 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 8.6 g (yield 71.4%) of <Intermediate 105-1> was obtained by extraction and concentration, followed by column and recrystallization.
(2) (2) 제조예manufacturing example 2 : 중간체 105-2의 합성 2: synthesis of intermediate 105-2
1-Bromo-4-chlorobenzene (10.0 g, 0.052 mol), 중간체 105-1 (33.9 g, 0.062 mol), K2CO3 (21.7 g, 0.156 mol), Pd(PPh3)4 (1.2 g, 1.04 mmol)에 Toluene 200 mL, EtOH 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 105-2>를 21.8 g (수율 79.6%) 수득하였다.1-Bromo-4-chlorobenzene (10.0 g, 0.052 mol), intermediate 105-1 (33.9 g, 0.062 mol), K 2 CO 3 (21.7 g, 0.156 mol), Pd(PPh 3 ) 4 (1.2 g, 1.04 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H 2 O, and reacted by stirring at 80 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 21.8 g of <Intermediate 105-2> (yield: 79.6%).
(3) (3) 제조예manufacturing example 3 : 중간체 105-3의 합성 3: synthesis of intermediate 105-3
1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), 9,9-Dimethylfluoren-2-boronic acid (21.1 g, 0.089 mol), K2CO3 (30.7 g, 0.222 mol), Pd(PPh3)4 (0.9 g, 0.74 mmol)에 Toluene 200 mL, EtOH 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 105-3>을 13.7 g (수율 74.5%) 수득하였다.1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), 9,9-Dimethylfluoren-2-boronic acid (21.1 g, 0.089 mol), K 2 CO 3 (30.7 g, 0.222 mol), Pd (PPh) 3 ) 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H 2 O were added to 4 (0.9 g, 0.74 mmol), followed by stirring at 80 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 13.7 g of <Intermediate 105-3> (yield: 74.5%).
(4) (4) 제조예manufacturing example 4 : 중간체 105-4의 합성 4: synthesis of intermediate 105-4
중간체 105-3 (10.0 g, 0.020 mol), Bis(pinacolato)diboron (13.9 g, 0.024 mol), KOAc (4.0 g, 0.040 mol), Pd(dppf)Cl2 (0.4 g, 0.6 mmol), X-Phos (0.4 g, 0.72 mmol)에 Dioxane 200 mL를 넣고 12시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 105-4>를 8.1 g (수율 68.4%) 수득하였다.Intermediate 105-3 (10.0 g, 0.020 mol), Bis(pinacolato)diboron (13.9 g, 0.024 mol), KOAc (4.0 g, 0.040 mol), Pd(dppf)Cl 2 (0.4 g, 0.6 mmol), X- Dioxane (200 mL) was added to Phos (0.4 g, 0.72 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 8.1 g (yield 68.4%) of <Intermediate 105-4> was obtained by extraction and concentration, followed by column and recrystallization.
(5) (5) 제조예manufacturing example 5 : 화합물 105의 합성 5: Synthesis of Compound 105
중간체 105-2 (10.0 g, 0.019 mol), 중간체 105-4 (13.5 g, 0.023 mol), K2CO3 (7.9 g, 0.057 mol), Pd(OAc)2 (1.1 g, 0.95 mmol), X-Phos (0.9 g, 1.9 mmol), THF 200 mL와 H2O 50 mL를 넣고 6시간 동안 90 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 105>를 12.7 g (수율 70.1%) 수득하였다.Intermediate 105-2 (10.0 g, 0.019 mol), Intermediate 105-4 (13.5 g, 0.023 mol), K 2 CO 3 (7.9 g, 0.057 mol), Pd(OAc) 2 (1.1 g, 0.95 mmol), X -Phos (0.9 g, 1.9 mmol), 200 mL of THF and 50 mL of H 2 O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted and concentrated, followed by column and recrystallization to obtain 12.7 g of <Compound 105> (yield: 70.1%).
LC/MS: m/z=950(M)+]LC/MS: m/z=950(M) + ]
합성예synthesis example 8 : 화합물 129의 합성 8: synthesis of compound 129
(1) (One) 제조예manufacturing example 1 : 중간체 129-1의 합성 1: synthesis of intermediate 129-1
2-Bromo-5-chloropyridine (10.0 g, 0.052 mol), 3,5-Bis(trifluoromethyl)phenylboronic acid (16.1 g, 0.062 mol), K2CO3 (21.6 g, 0.156 mol), Pd(PPh3)4 (1.2 g, 1.04 mmol)에 Toluene 200 mL, EtOH 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 129-1>을 12.7 g (수율 75.1%) 수득하였다.2-Bromo-5-chloropyridine (10.0 g, 0.052 mol), 3,5-Bis(trifluoromethyl)phenylboronic acid (16.1 g, 0.062 mol), K 2 CO 3 (21.6 g, 0.156 mol), Pd(PPh 3 ) 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H 2 O were added to 4 (1.2 g, 1.04 mmol) and reacted by stirring at 80 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 12.7 g of <Intermediate 129-1> (yield: 75.1%).
(2) (2) 제조예manufacturing example 2 : 중간체 129-2의 합성 2: synthesis of intermediate 129-2
중간체 129-1 (10.0 g, 0.031 mol), Bis(pinacolato)diboron (21.1 g, 0.037 mol), KOAc (6.0 g, 0.062 mol), Pd(dppf)Cl2 (0.7 g, 0.93 mmol), X-Phos (0.5 g, 1.11 mmol)에 Dioxane 200 mL를 넣고 12시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 129-2>를 9.1 g (수율 71.0%) 수득하였다.Intermediate 129-1 (10.0 g, 0.031 mol), Bis(pinacolato)diboron (21.1 g, 0.037 mol), KOAc (6.0 g, 0.062 mol), Pd(dppf)Cl 2 (0.7 g, 0.93 mmol), X- 200 mL of Dioxane was added to Phos (0.5 g, 1.11 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, after extraction and concentration, 9.1 g (yield 71.0%) of <Intermediate 129-2> was obtained by column.
(3) (3) 제조예manufacturing example 3 : 중간체 129-3의 합성 3: synthesis of intermediate 129-3
1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), 중간체 129-2 (37.0 g, 0.089 mol), K2CO3 (30.7 g, 0.222 mol), Pd(PPh3)4 (0.9 g, 0.74 mmol)에 Toluene 200 mL, EtOH 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 129-3>을 18.7 g (수율 73.2%) 수득하였다.1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), intermediate 129-2 (37.0 g, 0.089 mol), K 2 CO 3 (30.7 g, 0.222 mol), Pd(PPh 3 ) 4 (0.9 g , 0.74 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H 2 O, and reacted by stirring at 80 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 18.7 g of <Intermediate 129-3> (yield: 73.2%).
(4) (4) 제조예manufacturing example 4 : 중간체 129-4의 합성 4: synthesis of intermediate 129-4
중간체 129-3 (10.0 g, 0.015 mol), Bis(pinacolato)diboron (10.0 g, 0.018 mol), KOAc (2.8 g, 0.030 mol), Pd(dppf)Cl2 (0.3 g, 0.45 mmol), X-Phos (0.3 g, 0.54 mmol)에 Dioxane 200 mL를 넣고 12시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 129-4>를 7.6 g (수율 67.1%) 수득하였다.Intermediate 129-3 (10.0 g, 0.015 mol), Bis(pinacolato)diboron (10.0 g, 0.018 mol), KOAc (2.8 g, 0.030 mol), Pd(dppf)Cl 2 (0.3 g, 0.45 mmol), X- 200 mL of Dioxane was added to Phos (0.3 g, 0.54 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 7.6 g (yield: 67.1%) of <Intermediate 129-4> was obtained by extraction and concentration, followed by column and recrystallization.
(5) (5) 제조예manufacturing example 5 : 화합물 129의 합성 5: Synthesis of Compound 129
중간체 105-2 (10.0 g, 0.019 mol), 중간체 129-4 (17.9 g, 0.023 mol), K2CO3 (7.9 g, 0.057 mol), Pd(OAc)2 (1.1 g, 0.95 mmol), X-Phos (0.9 g, 1.9 mmol), THF 200 mL와 H2O 50 mL를 넣고 6시간 동안 90 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 129>를 14.2 g (수율 65.1%) 수득하였다.Intermediate 105-2 (10.0 g, 0.019 mol), Intermediate 129-4 (17.9 g, 0.023 mol), K 2 CO 3 (7.9 g, 0.057 mol), Pd(OAc) 2 (1.1 g, 0.95 mmol), X -Phos (0.9 g, 1.9 mmol), 200 mL of THF and 50 mL of H 2 O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 14.2 g of <Compound 129> (yield: 65.1%).
LC/MS: m/z=1144(M)+]LC/MS: m/z=1144(M) + ]
합성예synthesis example 9 : 화합물 139의 합성 9: synthesis of compound 139
(1) (One) 제조예manufacturing example 1 : 중간체 139-1의 합성 1: synthesis of intermediate 139-1
1-Bromo-4-tert-butylbenzene (10.0 g, 0.047 mol), 2-Aminobenzotrifluoride (11.3 g, 0.071 mol), NaOtBu (13.5 g, 0.142 mol), Pd(dba)2 (1.1 g, 1.88 mmol), t-Bu3P (0.8 g, 3.76 mmol)에 Toluene 150 mL를 넣고 4시간 동안 70 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 139-1>을 9.7 g (수율 70.5%) 수득하였다.1-Bromo-4-tert-butylbenzene (10.0 g, 0.047 mol), 2-Aminobenzotrifluoride (11.3 g, 0.071 mol), NaOtBu (13.5 g, 0.142 mol), Pd(dba) 2 (1.1 g, 1.88 mmol), 150 mL of Toluene was added to t-Bu 3 P (0.8 g, 3.76 mmol), followed by stirring at 70 °C for 4 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 9.7 g of <Intermediate 139-1> (yield: 70.5%).
(2) (2) 제조예manufacturing example 2 : 중간체 139-2의 합성 2: synthesis of intermediate 139-2
1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), 중간체 139-1 (32.6 g, 0.111 mol), NaOtBu (21.3 g, 0.222 mol), Pd(dba)2 (0.9 g, 1.48 mmol), t-Bu3P (0.6 g, 2.96 mmol)에 Toluene 150 mL를 넣고 4시간 동안 70 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 139-2>를 18.9 g (수율 73.5%) 수득하였다.1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), intermediate 139-1 (32.6 g, 0.111 mol), NaOtBu (21.3 g, 0.222 mol), Pd(dba) 2 (0.9 g, 1.48 mmol) , Toluene 150 mL was added to t-Bu 3 P (0.6 g, 2.96 mmol) and reacted by stirring at 70 °C for 4 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 18.9 g of <Intermediate 139-2> (yield: 73.5%).
(3) (3) 제조예manufacturing example 3 : 중간체 139-3의 합성 3: synthesis of intermediate 139-3
중간체 139-2 (10.0 g, 0.014 mol), Bis(pinacolato)diboron (9.9 g, 0.017 mol), KOAc (2.8 g, 0.028 mol), Pd(dppf)Cl2 (0.3 g, 0.42 mmol), X-Phos (0.3 g, 0.51 mmol)에 Dioxane 200 mL를 넣고 12시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 139-3>을 7.3 g (수율 64.5%) 수득하였다.Intermediate 139-2 (10.0 g, 0.014 mol), Bis(pinacolato)diboron (9.9 g, 0.017 mol), KOAc (2.8 g, 0.028 mol), Pd(dppf)Cl 2 (0.3 g, 0.42 mmol), X- Dioxane (200 mL) was added to Phos (0.3 g, 0.51 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 7.3 g (yield 64.5%) of <Intermediate 139-3> was obtained by extraction and concentration, followed by column and recrystallization.
(4) (4) 제조예manufacturing example 4 : 화합물 139의 합성 4: Synthesis of Compound 139
중간체 105-2 (10.0 g, 0.019 mol), 중간체 139-3 (18.0 g, 0.023 mol), K2CO3 (7.9 g, 0.057 mol), Pd(OAc)2 (1.1 g, 0.95 mmol), X-Phos (0.9 g, 1.9 mmol), THF 200 mL와 H2O 50 mL를 넣고 6시간 동안 90 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 139>를 14.5 g (수율 66.2%) 수득하였다.Intermediate 105-2 (10.0 g, 0.019 mol), Intermediate 139-3 (18.0 g, 0.023 mol), K 2 CO 3 (7.9 g, 0.057 mol), Pd(OAc) 2 (1.1 g, 0.95 mmol), X -Phos (0.9 g, 1.9 mmol), 200 mL of THF and 50 mL of H 2 O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 14.5 g of <Compound 139> (yield: 66.2%).
LC/MS: m/z=1148(M)+]LC/MS: m/z=1148(M) + ]
합성예synthesis example 10 : 화합물 181의 합성 10: synthesis of compound 181
(1) (One) 제조예manufacturing example 1 : 중간체 181-1의 합성 1: synthesis of intermediate 181-1
2-Bromo-6-chloronaphthalene (10.0 g, 0.041 mol), 중간체 105-1 (26.8 g, 0.049 mol), K2CO3 (17.2 g, 0.123 mol), Pd(PPh3)4 (1.0 g, 0.82 mmol)에 Toluene 200 mL, EtOH 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 181-1>을 17.9 g (수율 75.2%) 수득하였다.2-Bromo-6-chloronaphthalene (10.0 g, 0.041 mol), intermediate 105-1 (26.8 g, 0.049 mol), K 2 CO 3 (17.2 g, 0.123 mol), Pd(PPh 3 ) 4 (1.0 g, 0.82 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H 2 O, and reacted by stirring at 80 °C for 6 hours. After completion of the reaction, 17.9 g (yield 75.2%) of <Intermediate 181-1> was obtained by extraction and concentration, followed by column and recrystallization.
(2) (2) 제조예manufacturing example 2 : 화합물 181의 합성 2: Synthesis of Compound 181
중간체 181-1 (10.0 g, 0.017 mol), 중간체 17-2 (12.1 g, 0.020 mol), K2CO3 (7.2 g, 0.051 mol), Pd(OAc)2 (1.0 g, 0.85 mmol), X-Phos (0.8 g, 1.7 mmol), THF 200 mL와 H2O 50 mL를 넣고 6시간 동안 90 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 181>을 12.6 g (수율 72.9%) 수득하였다.Intermediate 181-1 (10.0 g, 0.017 mol), Intermediate 17-2 (12.1 g, 0.020 mol), K 2 CO 3 (7.2 g, 0.051 mol), Pd(OAc) 2 (1.0 g, 0.85 mmol), X -Phos (0.8 g, 1.7 mmol), 200 mL of THF and 50 mL of H 2 O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 12.6 g of <Compound 181> (yield: 72.9%).
LC/MS: m/z=992(M)+]LC/MS: m/z=992(M) + ]
합성예synthesis example 11 : 화합물 191의 합성 11: synthesis of compound 191
(1) (One) 제조예manufacturing example 1 : 화합물 191의 합성 1: Synthesis of Compound 191
중간체 181-1 (10.0 g, 0.017 mol), 중간체 42-2 (7.7 g, 0.020 mol), K2CO3 (7.2 g, 0.051 mol), Pd(OAc)2 (1.0 g, 0.85 mmol), X-Phos (0.8 g, 1.7 mmol), THF 200 mL와 H2O 50 mL를 넣고 6시간 동안 90 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 191>을 9.3 g (수율 68.3%) 수득하였다.Intermediate 181-1 (10.0 g, 0.017 mol), Intermediate 42-2 (7.7 g, 0.020 mol), K 2 CO 3 (7.2 g, 0.051 mol), Pd(OAc) 2 (1.0 g, 0.85 mmol), X -Phos (0.8 g, 1.7 mmol), 200 mL of THF and 50 mL of H 2 O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 9.3 g of <Compound 191> (yield: 68.3%).
LC/MS: m/z=782(M)+]LC/MS: m/z=782(M) + ]
소자 device 실시예Example (CPL) (CPL)
본 발명에 따른 실시예에서, 양극은 25 mm × 25 mm × 0.7 mm의 Ag를 포함하는 ITO 유리 기판을 이용하여, 발광 면적이 2 mm × 2 mm 크기가 되도록 패터닝한 후 세정하였다. 패터닝된 ITO 기판을 진공 챔버에 장착한 후, 1 × 10-6 torr 이상의 공정 압력에서 기판 위에 하기 구조로 유기물과 금속을 증착하였다.In an example according to the present invention, the anode was patterned to have a light emitting area of 2 mm × 2 mm using an ITO glass substrate containing Ag of 25 mm × 25 mm × 0.7 mm, and then washed. After mounting the patterned ITO substrate in a vacuum chamber, an organic material and a metal were deposited on the substrate at a process pressure of 1 × 10 -6 torr or more in the following structure.
소자 device 실시예Example 1 내지 31 1 to 31
본 발명에 따라 구현되는 화합물을 소자에 구비되는 광효율 개선층에 채용하여, 하기와 같은 소자 구조를 갖는 유기발광소자를 제작 후, 본 발명에 따라 구현되는 화합물과 이를 포함하는 소자가 갖는 발광 및 구동 특성을 측정하였다.After employing the compound implemented according to the present invention in the light efficiency improvement layer provided in the device to manufacture an organic light emitting device having the following device structure, light emission and driving of the compound implemented according to the present invention and the device including the same properties were measured.
Ag/ITO / 정공주입층 (HAT-CN, 5 nm) / 정공수송층 (α-NPB, 100 nm) / 전자저지층 (EB1, 10 nm) / 발광층 (20 nm) / 전자수송층 (ET1:Liq, 30 nm) / LiF (1 nm) / Mg:Ag (15 nm) / 광효율 개선층 (70 nm)Ag/ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (α-NPB, 100 nm) / electron blocking layer (EB1, 10 nm) / light emitting layer (20 nm) / electron transport layer (ET1:Liq, 30 nm) / LiF (1 nm) / Mg:Ag (15 nm) / light efficiency improvement layer (70 nm)
유리 기판상에 Ag를 포함하는 ITO 투명 전극 상부에 [HAT-CN]을 5 nm 두께로 성막하여 정공주입층을 형성하고, [α-NPB]를 100 nm로 성막하여 정공수송층을 형성하였으며, [EB1]을 10 nm 두께로 성막하여 전자저지층을 형성하였다. 이후, 호스트 화합물로 [BH1], 도펀트 화합물로 [BD1]을 사용하여 20 nm로 공증착하여 발광층을 형성하였으며, 전자수송층 (하기 [201] 화합물 Liq 50% 도핑)을 30 nm 증착한 후, LiF를 1 nm의 두께로 성막하여 전자주입층을 형성하였으며, Mg:Ag를 1:9의 비율로 15 nm의 두께로 성막하여 캐소드를 형성하였다. 그리고, 광효율 개선층 (capping layer)은 본 발명으로 구현되는 화합물로 70 nm의 두께로 성막하여 유기발광소자를 제작하였다.A hole injection layer was formed by depositing [HAT-CN] to a thickness of 5 nm on top of an ITO transparent electrode containing Ag on a glass substrate, and a hole transport layer was formed by depositing [α-NPB] to a thickness of 100 nm, [ EB1] was formed to a thickness of 10 nm to form an electron blocking layer. Thereafter, [BH1] as a host compound and [BD1] as a dopant compound were used to form a light emitting layer by co-evaporation to 20 nm, and an electron transport layer (50% doped with Liq of [201] compound) was deposited at 30 nm, followed by LiF was formed to a thickness of 1 nm to form an electron injection layer, and Mg:Ag was formed to a thickness of 15 nm at a ratio of 1:9 to form a cathode. In addition, a light efficiency improvement layer (capping layer) was formed to a thickness of 70 nm with a compound implemented according to the present invention to manufacture an organic light emitting device.
소자 device 비교예comparative example 1 One
소자 비교예 1을 위한 유기발광소자는 상기 실시예 1 내지 31의 소자구조에서 광효율 개선층을 구비하지 않는 점을 제외하고 동일하게 제작하였다.The organic light emitting device for Device Comparative Example 1 was manufactured in the same manner as the device structures of Examples 1 to 31, except that the light efficiency improving layer was not provided.
소자 device 비교예comparative example 2 2
소자 비교예 2를 위한 유기발광소자는 상기 실시예 1 내지 31의 소자구조에서 광효율 개선층 화합물로 본 발명에 따른 화합물 대신 Alq3를 사용한 것을 제외하고 동일하게 제작하였다.The organic light emitting device for Device Comparative Example 2 was manufactured in the same manner as in the device structures of Examples 1 to 31, except that Alq 3 was used instead of the compound according to the present invention as a light efficiency improving layer compound.
실험예Experimental example 1 : 소자 1: element 실시예Example 1 내지 31의 발광 특성 Luminescence characteristics of 1 to 31
상기 실시예 및 비교예에 따라 제조된 유기발광소자에 대해서 Source meter (Model 237, Keithley)와 휘도계 (PR-650, Photo Research)를 이용하여 구동 전압, 전류 효율 및 색좌표를 측정하였고, 1,000 nit 기준의 결과값은 하기 [표 1]과 같다.Driving voltage, current efficiency and color coordinates were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research) for the organic light emitting device manufactured according to the above Examples and Comparative Examples, 1,000 nit The standard result values are shown in [Table 1] below.
상기 [표 1]에 나타낸 결과를 살펴보면, 본 발명에 따른 화합물을 소자에 구비되는 광효율 개선층에 채용한 유기발광소자의 경우 종래 광효율 개선층을 구비하지 않은 소자 및 종래에 광효율 개선층 재료로 사용되고 있는 화합물을 채용한 소자 (비교예 1 및 2)에 비하여 구동 전압이 감소하고, 전류 효율이 향상되는 것을 확인할 수 있다.Looking at the results shown in [Table 1], in the case of an organic light emitting device employing the compound according to the present invention in the light efficiency improvement layer provided in the device, it is used as a conventional light efficiency improvement layer material and a device without a light efficiency improvement layer. It can be confirmed that the driving voltage is reduced and the current efficiency is improved compared to the devices (Comparative Examples 1 and 2) employing the compound having the compound.
[HAT_CN] [α-NPB] [BH1] [BD1] [ET1][HAT_CN] [α-NPB] [BH1] [BD1] [ET1]
[EB1][EB1]
Claims (5)
[화학식 Ⅰ]
상기 [화학식 Ⅰ]에서,
L은 각각 독립적으로 직접 결합이거나, 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기 및 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴렌기 중에서 선택되는 어느 하나이고,
n은 0 내지 3의 정수이며, 상기 n이 2이상인 경우 복수 개의 L은 서로 동일하거나 상이하고,
Ar1 및 Ar2는 서로 동일하거나 상이하며, 각각 독립적으로 중수소 (D), 시아노기 (CN), 할로겐기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 알콕시기, 치환 또는 비치환된 탄소수 1 내지 20의 할로겐화된 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 할로겐화된 알콕시기, 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 헤테로시클로알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴기 및 치환 또는 비치환된 아민기 중에서 선택되는 어느 하나이다.A compound represented by the following [Formula I]:
[Formula I]
In the above [Formula I],
L is each independently a direct bond, or any one selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms,
n is an integer from 0 to 3, and when n is 2 or more, a plurality of L's are the same as or different from each other;
Ar 1 and Ar 2 are the same as or different from each other, and are each independently deuterium (D), a cyano group (CN), a halogen group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Alkoxy group, substituted or unsubstituted halogenated alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted halogenated alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted It is any one selected from a heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and a substituted or unsubstituted amine group.
상기 L, Ar1 및 Ar2의 정의에서 '치환 또는 비치환된'이라 함은 상기 L, Ar1 및 Ar2가 각각 중수소, 할로겐기, 시아노기, 알킬기, 할로겐화된 알킬기, 중수소화된 알킬기, 시클로알킬기, 헤테로시클로알킬기, 알콕시기, 할로겐화된 알콕시기, 중수소화된 알콕시기, 아릴기, 헤테로아릴기, 알킬실릴기, 아릴실릴기 및 카르보닐기 중에서 선택된 1 또는 2 이상의 치환기로 치환되거나, 상기 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미하는 화합물.According to claim 1,
In the definition of L, Ar 1 and Ar 2 , 'substituted or unsubstituted' means that L, Ar 1 and Ar 2 are deuterium, a halogen group, a cyano group, an alkyl group, a halogenated alkyl group, a deuterated alkyl group, Substituted with one or two or more substituents selected from a cycloalkyl group, a heterocycloalkyl group, an alkoxy group, a halogenated alkoxy group, a deuterated alkoxy group, an aryl group, a heteroaryl group, an alkylsilyl group, an arylsilyl group, and a carbonyl group, or the above substituents A compound which means that two or more of the substituents are substituted with linked substituents or have no substituents.
상기 [화학식 Ⅰ]은 하기 [화합물 1] 내지 [화합물 206] 중에서 선택되는 어느 하나인 화합물:
[Formula I] is any one compound selected from the following [Compound 1] to [Compound 206]:
상기 제1 전극과 제2 전극의 상부 또는 하부 중에서 상기 유기층과 반대되는 적어도 일측에 형성되는 광효율 개선층 (Capping layer)을 더 포함하고,
상기 광효율 개선층은 상기 [화학식 Ⅰ]로 표시되는 화합물을 포함하는 유기발광소자.An organic light emitting device comprising a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode,
Further comprising a light efficiency improvement layer (Capping layer) formed on at least one side opposite to the organic layer among the upper or lower portions of the first electrode and the second electrode,
The light efficiency improving layer is an organic light emitting device including a compound represented by [Chemical Formula I].
상기 광효율 개선층은 상기 제1 전극의 하부 또는 상기 제2 전극의 상부 중 적어도 하나에 형성되는 유기발광소자.According to claim 4,
The light efficiency improving layer is formed on at least one of a lower portion of the first electrode and an upper portion of the second electrode.
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