KR20220084559A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents
An electroluminescent compound and an electroluminescent device comprising the same Download PDFInfo
- Publication number
- KR20220084559A KR20220084559A KR1020200174143A KR20200174143A KR20220084559A KR 20220084559 A KR20220084559 A KR 20220084559A KR 1020200174143 A KR1020200174143 A KR 1020200174143A KR 20200174143 A KR20200174143 A KR 20200174143A KR 20220084559 A KR20220084559 A KR 20220084559A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- light emitting
- mol
- layer
- organic light
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 50
- 239000010410 layer Substances 0.000 claims abstract description 62
- 239000012044 organic layer Substances 0.000 claims abstract description 23
- 238000002347 injection Methods 0.000 claims description 19
- 239000007924 injection Substances 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 230000005525 hole transport Effects 0.000 claims description 11
- 230000000903 blocking effect Effects 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 125000005264 aryl amine group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 229940125904 compound 1 Drugs 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000592 heterocycloalkyl group Chemical group 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
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 description 52
- 238000003786 synthesis reaction Methods 0.000 description 52
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- 238000006243 chemical reaction Methods 0.000 description 44
- -1 1-methylpentyl group Chemical group 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 238000004519 manufacturing process Methods 0.000 description 32
- 239000000463 material Substances 0.000 description 31
- 238000000605 extraction Methods 0.000 description 30
- 238000001953 recrystallisation Methods 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 13
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 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
- 239000000758 substrate Substances 0.000 description 6
- 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 5
- 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 5
- 239000011368 organic material Substances 0.000 description 5
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 3
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 3
- BGGALFIXXQOTPY-NRFANRHFSA-N C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC Chemical compound C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC BGGALFIXXQOTPY-NRFANRHFSA-N 0.000 description 3
- 229940127007 Compound 39 Drugs 0.000 description 3
- POFVJRKJJBFPII-UHFFFAOYSA-N N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1(CCCC1)NC=1SC(=C(N=1)C)C1=NC(=NC=C1F)NC1=NC=C(C=C1)CN1CCN(CC1)CC POFVJRKJJBFPII-UHFFFAOYSA-N 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
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 3
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229940127204 compound 29 Drugs 0.000 description 3
- 229940125877 compound 31 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 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
- 125000003367 polycyclic group Chemical group 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical group C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-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
- 150000001412 amines Chemical group 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
- 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
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 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
- UWMISBRPSJFHIR-UHFFFAOYSA-N naphtho[2,3-b][1]benzothiole Chemical compound C1=CC=C2C=C3C4=CC=CC=C4SC3=CC2=C1 UWMISBRPSJFHIR-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000002894 organic compounds Chemical class 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
- 239000002356 single layer Substances 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
- 125000001425 triazolyl group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- YBNDRTRLXPEWKQ-UHFFFAOYSA-N (4-chloro-2-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1F YBNDRTRLXPEWKQ-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 compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 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
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-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
- OTJZMNIBLUCUJZ-UHFFFAOYSA-N 2,4-diphenyl-1,3,5-triazine Chemical compound C1=CC=CC=C1C1=NC=NC(C=2C=CC=CC=2)=N1 OTJZMNIBLUCUJZ-UHFFFAOYSA-N 0.000 description 1
- LONBOJIXBFUBKQ-UHFFFAOYSA-N 2,7-dibromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC(Br)=CC=C3C2=C1 LONBOJIXBFUBKQ-UHFFFAOYSA-N 0.000 description 1
- HJMVGLYGWVBAND-UHFFFAOYSA-N 2-(4-bromophenyl)-4,6-dinaphthalen-1-yl-1,3,5-triazine Chemical compound C1=CC(Br)=CC=C1C1=NC(C=2C3=CC=CC=C3C=CC=2)=NC(C=2C3=CC=CC=C3C=CC=2)=N1 HJMVGLYGWVBAND-UHFFFAOYSA-N 0.000 description 1
- UZBYKKGCTOQGOM-UHFFFAOYSA-N 2-(4-bromophenyl)-4,6-dinaphthalen-2-yl-1,3,5-triazine Chemical compound BrC1=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC2=CC=CC=C2C=C1)C1=CC2=CC=CC=C2C=C1 UZBYKKGCTOQGOM-UHFFFAOYSA-N 0.000 description 1
- NTEIZPBYXABJKN-UHFFFAOYSA-N 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound C1=CC(Cl)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 NTEIZPBYXABJKN-UHFFFAOYSA-N 0.000 description 1
- FVQBRDRAILXTMJ-UHFFFAOYSA-N 2-chloro-4,6-bis(4-phenylphenyl)-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC=1C(C=C1)=CC=C1C1=CC=CC=C1 FVQBRDRAILXTMJ-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
- 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
- XSJLDNSNUICSQC-UHFFFAOYSA-N 4,6-dibromodibenzofuran Chemical compound O1C2=C(Br)C=CC=C2C2=C1C(Br)=CC=C2 XSJLDNSNUICSQC-UHFFFAOYSA-N 0.000 description 1
- PQNQMYMGUXGWTG-UHFFFAOYSA-N 4-bromonaphthalen-2-ol Chemical compound C1=CC=CC2=CC(O)=CC(Br)=C21 PQNQMYMGUXGWTG-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- SNUKBTHMZLUJKR-UHFFFAOYSA-N 9-bromo-7,7-dimethylbenzo[c]fluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=C(C=CC=C4)C4=C3C2=C1 SNUKBTHMZLUJKR-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
- 101100016516 Caenorhabditis elegans hbl-1 gene Proteins 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
- 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- PTTJBNMNZAUITF-UHFFFAOYSA-N [4-(1,3-benzoxazol-2-yl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=NC2=CC=CC=C2O1 PTTJBNMNZAUITF-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 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
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- MFMVRILBADIIJO-UHFFFAOYSA-N benzo[e][1]benzofuran Chemical compound C1=CC=C2C(C=CO3)=C3C=CC2=C1 MFMVRILBADIIJO-UHFFFAOYSA-N 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
- 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
- 229910052794 bromium Inorganic materials 0.000 description 1
- 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
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005266 diarylamine group Chemical group 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
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect 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
- 238000007429 general method Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 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
- 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
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- 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
- 125000001041 indolyl group Chemical group 0.000 description 1
- 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
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000005921 isopentoxy group Chemical group 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 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
- 239000011777 magnesium Substances 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- FTMRMQALUDDFQO-UHFFFAOYSA-N naphtho[2,3-b][1]benzofuran Chemical compound C1=CC=C2C=C3C4=CC=CC=C4OC3=CC2=C1 FTMRMQALUDDFQO-UHFFFAOYSA-N 0.000 description 1
- 239000007773 negative electrode material Substances 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
- 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
- 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
- JCDAUYWOHOLVMH-UHFFFAOYSA-N phenanthren-9-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC3=CC=CC=C3C2=C1 JCDAUYWOHOLVMH-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
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 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
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 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
- 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
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(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
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- 238000007740 vapor deposition Methods 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H01L51/5012—
-
- H01L51/5056—
-
- H01L51/5072—
-
- H01L51/5088—
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
본 발명은 유기발광소자 내의 전자수송층 등의 유기층에 채용되어 소자의 저전압 구동과 우수한 발광 효율 등의 발광 특성을 구현할 수 있는 [화학식 Ⅰ]로 표시되는 신규한 유기발광 화합물 및 이를 포함하는 유기발광소자에 관한 것이다.
[화학식 Ⅰ]
The present invention is a novel organic light emitting compound represented by [Formula I] that is employed in an organic layer such as an electron transport layer in an organic light emitting device to realize light emitting characteristics such as low voltage driving and excellent luminous efficiency of the device, and an organic light emitting device comprising the same is about
[Formula Ⅰ]
Description
본 발명은 유기발광 화합물에 관한 것으로서, 더욱 상세하게는 유기발광소자 내의 유기층 재료로 채용되는 것을 특징으로 하는 유기발광 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 compound, and more particularly, to an organic light emitting compound, characterized in that it is employed as an organic layer material in an organic light emitting device, and an organic light emitting property with significantly improved light emitting properties such as low voltage driving and excellent luminous efficiency of the device by employing the same It relates to a light emitting device.
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.The organic light emitting device can be formed on a transparent substrate as well as being able to drive at a low voltage of 10 V or less compared to a plasma display panel or an inorganic electroluminescent (EL) display, and consume relatively little power. , has the advantage of excellent color, and can represent three colors of green, blue, and red.
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 such an organic light emitting device to exhibit the above characteristics, the material constituting the organic layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, and an electron injection material, is supported by stable and efficient materials. However, the development of a stable and efficient organic layer material for an organic light emitting device has not yet been sufficiently developed.
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 realize a more stable organic light emitting device, and to achieve high efficiency, long lifespan, and large size of the device, additional improvements are required in terms of efficiency and lifespan characteristics. It is desperately needed.
따라서, 본 발명은 유기발광소자 내의 유기층에 채용되어 소자의 저전압 구동과 향상된 발광 효율 등의 우수한 발광 특성을 구현할 수 있는 신규한 유기발광 화합물 및 이를 포함하는 유기발광소자를 제공하고자 한다.Accordingly, an object of the present invention is to provide a novel organic light emitting compound capable of implementing excellent light emitting characteristics such as low voltage driving and improved luminous efficiency of the device by being employed in the organic layer in the organic light emitting device, and an organic light emitting device including the same.
본 발명은 상기 과제를 해결하기 위하여, 하기 [화학식 Ⅰ]로 표시되는 유기발광 화합물을 제공한다.In order to solve the above problems, the present invention provides an organic light emitting compound represented by the following [Formula I].
[화학식 Ⅰ][Formula Ⅰ]
상기 [화학식 Ⅰ]의 특징적인 구조와 이에 의하여 구현되는 화합물, X, L, Ar1 내지 Ar2에 대해서는 후술하기로 한다.The characteristic structure of the [Formula I] and the compounds implemented thereby, X, L, Ar 1 to Ar 2 will be described later.
본 발명에 따른 유기발광 화합물을 유기발광소자 내의 전자수송층 등의 유기층 재료로 채용할 경우에 소자의 저전압 구동과 우수한 발광 효율 등의 발광 특성을 구현할 수 있어 다양한 디스플레이 소자에 유용하게 사용될 수 있다.When the organic light emitting compound according to the present invention is employed as an organic layer material such as an electron transport layer in an organic light emitting device, it is possible to realize light emitting characteristics such as low voltage driving and excellent luminous efficiency of the device, so that it can be usefully used in various display devices.
이하, 본 발명을 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명은 유기발광소자의 소자의 저전압 구동과 우수한 발광 효율 등의 발광 특성을 거둘 수 있는 하기 [화학식 Ⅰ]로 표시되는 유기발광 화합물에 관한 것으로서,The present invention relates to an organic light-emitting compound represented by the following [Formula I], which can achieve light-emitting characteristics such as low voltage driving of the organic light-emitting device and excellent light-emitting efficiency,
구조적으로 하기 [화학식 Ⅰ]로 표시되는 골격 구조, 즉 시아노기(CN)가 결합된 벤조나프토퓨란, 벤조나프토티오펜 또는 벤조플루오렌 구조에 L 연결기를 통한 트리아진 유도체를 도입한 것을 특징으로 하고, 이러한 구조적 특징을 통하여 유기발광소자의 저전압 구동 특성, 발광 효율 특성을 향상시킬 수 있다.It is characterized by introducing a triazine derivative through an L linkage into a skeletal structure structurally represented by the following [Formula I], that is, a benzonaphthofuran, benzonaphthothiophene or benzofluorene structure to which a cyano group (CN) is bonded. And, it is possible to improve the low voltage driving characteristics and luminous efficiency characteristics of the organic light emitting diode through these structural features.
[화학식 Ⅰ][Formula Ⅰ]
상기 [화학식 Ⅰ]에서,In the [Formula I],
X는 O, S 또는 C(CH3)2이다.X is O, S or C(CH 3 ) 2 .
L은 단일결합이거나, 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴렌기 중에서 선택되고, n은 0 내지 3의 정수이고, n이 2 이상인 경우 복수 개의 L은 서로 동일하거나 상이하다.L is a single bond, or is selected from a substituted or unsubstituted C6 to C30 arylene group and a substituted or unsubstituted C3 to C30 heteroarylene group, n is an integer from 0 to 3, and n is 2 or more A plurality of L's are the same as or different from each other.
Ar1 내지 Ar2는 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기 중에서 선택된다.Ar 1 To Ar 2 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, a substituted or unsubstituted C It is selected from an aryl group having 6 to 30 and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
또한, 본 발명의 일 실시예에 의하면, 상기 Ar1 내지 Ar2는 각각 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기 중에서 선택된다.In addition, according to an embodiment of the present invention, Ar 1 to Ar 2 are each selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
또한, 본 발명의 일 실시예에 의하면, 상기 Ar1 내지 Ar2는 각각 다양한 구조를 갖는 치환 또는 비치환된 아릴기 내지 헤테로아릴기일 수 있으며, Ar1 내지 Ar2는 각각 골격 구조와 동일하게 벤조나프토퓨란, 벤조나프토티오펜 또는 벤조플루오렌일 수도 있다.In addition, according to an embodiment of the present invention, Ar One To Ar 2 Each may be a substituted or unsubstituted aryl group to a heteroaryl group having various structures, Ar One To Ar 2 Each is benzo the same as the skeleton structure It may be naphthofuran, benzonaphthothiophene or benzofluorene.
한편, 상기 L, Ar1 내지 Ar2의 정의에서, '치환 또는 비치환된'이라 함은 L, Ar1 내지 Ar2가 각각 중수소, 중수소, 할로겐기, 시아노기, 니트로기, 히드록시기, 실릴기, 알킬기, 할로겐화된 알킬기, 중수소화된 알킬기, 시클로알킬기, 헤테로시클로알킬기, 알콕시기, 할로겐화된 알콕시기, 중수소화된 알콕시기, 아릴기, 헤테로아릴기, 알킬아민기, 아릴아민기 및 실릴기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되거나, 상기 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것인 것을 의미한다.Meanwhile, in the definition of L, Ar 1 to Ar 2 , 'substituted or unsubstituted' means that L and Ar 1 to Ar 2 are deuterium, deuterium, halogen group, cyano group, nitro group, hydroxyl group, silyl group, respectively. , an alkyl group, a halogenated alkyl group, a deuterated 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 alkylamine group, an arylamine group and a silyl group. It means that it is substituted with one or two or more substituents selected from the group consisting of, or substituted with a substituent to which two or more of the substituents are connected, or does not have any substituents.
구체적인 예를 들면, 치환된 아릴기라 함은, 페닐기, 비페닐기, 나프탈렌기, 플루오레닐기, 파이레닐기, 페난트레닐기, 페릴렌기, 테트라세닐기, 안트라센닐기 등이 다른 치환기로 치환된 것을 의미한다.For specific examples, the substituted aryl group means that 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. are substituted with other substituents do.
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 다른 치환기로 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 a condensed heterocyclic group thereof, such as a benzquinoline group. , a benzimidazole group, a benzoxazole group, a benzthiazole group, a benzcarbazole group, a dibenzothiophenyl group, a dibenzofuran group, and the like are substituted with other 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 the present invention is not limited thereto.
본 발명에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 20인 것이 바람직하다. 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 linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, 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, cyclopentylmethyl 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, and the like, but is not limited thereto.
본 발명에 있어서, 알콕시기는 직쇄 또는 분지쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 입체적 방해를 주지 않는 범위인 1 내지 20개인 것이 바람직하다. 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. Although the number of carbon atoms of the alkoxy group is not particularly limited, it is preferably 1 to 20 in a range that does not cause steric hindrance. 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 , a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.
본 발명에 있어서, 중수소화된 알킬기 또는 알콕시기, 할로겐화된 알킬기 또는 알콕시기는 상기 알킬기 또는 알콕시기가 중수소 또는 할로겐기로 치환된 알킬기 또는 알콕시기를 의미한다.In the present invention, a deuterated alkyl group or alkoxy group, halogenated alkyl group or alkoxy group means an alkyl group or alkoxy group in which the alkyl group or alkoxy group is substituted with deuterium or a halogen group.
본 발명에 있어서, 아릴기는 단환식 또는 다환식일 수 있고, 탄소수는 특별히 한정되지 않으나 6 내지 30인 것이 바람직하다. 단환식 아릴기의 예로는 페닐기, 비페닐기, 터페닐기, 스틸벤기 등이 있고, 다환식 아릴기의 예로는 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 테트라세닐기, 크라이세닐기, 플루오레닐기, 아세나프타센닐기, 트리페닐렌기, 플루오안트렌(fluoranthrene)기 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. Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and a stilbene group. Examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, and a tetracenyl group. , chrysenyl group, fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthrene group, etc., but the scope of the present invention is not limited to these examples.
본 발명에 있어서, 플루오레닐기는 2개의 고리 유기화합물이 1개의 원자를 통하여 연결된 구조로서, 예로는 , , 등이 있다.In the present invention, the fluorenyl group is a structure in which two ring organic compounds are connected through one atom, for example, , , etc.
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 , 등이 있다.In the present invention, the fluorenyl group includes a structure of an open fluorenyl group, wherein the open fluorenyl group is a structure in which one ring compound is disconnected in a structure in which two ring organic compounds are connected through one atom. , for example , etc.
또한, 상기 고리의 탄소원자는 N, S 및 O 중에서 선택되는 어느 하나 이상의 헤테로원자로 치환될 수 있으며, 예로는 , , , 등이 있다.In addition, the carbon atom of the ring may be substituted with any one or more heteroatoms selected from N, S and O, for example, , , , etc.
본 발명에 있어서, 헤테로아릴기는 이종원자로 O, N 또는 S를 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 30인 것이 바람직하며, 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 2 to 30 carbon atoms, and for a specific example thereof in the present invention, a thiophene group , furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyra Zinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxa Zol group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadia and a zolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, a phenoxazine group, a phenothiazine group, and the like, but are not limited thereto.
본 발명에 있어서, 실릴기는 비치환된 실릴기 또는 알킬기, 아릴기 등으로 치환된 실릴기로서, 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 a silyl group substituted with an alkyl group, an aryl group, etc., and specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxy phenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, and the like, but is not limited thereto.
본 발명에 있어서, 아민기는 -NH2, 알킬아민기, 아릴아민기 등일 수 있고, 아릴아민기는 아릴로 치환된 아민을 의미하고, 알킬아민기는 알킬로 치환된 아민을 의미하는 것이며, 아릴아민기의 예로는 치환 또는 비치환된 모노아릴아민기, 치환 또는 비치환된 디아릴아민기, 또는 치환 또는 비치환된 트리아릴아민기가 있고, 상기 아릴아민기 중의 아릴기는 상기 아릴기의 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, etc., the arylamine group means an amine substituted with an aryl, the alkylamine group means an amine substituted with an alkyl, and an arylamine group Examples of these include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group, and the aryl group in the arylamine group is the same as the definition of the aryl group, , The alkyl group of the alkylamine group is also the same as the definition of the alkyl group.
본 발명에서 사용되는 치환기인 할로겐기의 구체적인 예로는 플루오르(F), 클로린(Cl), 브롬(Br) 등을 들 수 있다.Specific examples of the halogen group as a substituent used in the present invention include fluorine (F), chlorine (Cl), bromine (Br), and the like.
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 spiro alkyl radicals, and preferably contains 3 to 20 ring carbon atoms, cyclopropyl, cyclopentyl, cyclohexyl, bicyclo heptyl, spirodecyl, spirodecyl, adamantyl, and the like, wherein 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, wherein one or more heteroatoms are O, S, N, P, B, Si, and Se , Preferably it is selected from O, N or S, and specifically, when N is included, it may be aziridine, pyrrolidine, piperidine, azepane, azocan, and the like.
상기 [화학식 Ⅰ]로 표시되는 본 발명에 따른 유기발광 화합물은 그 구조적 특이성으로 인하여 유기발광소자 내의 전자수송층을 포함하여 다양한 유기층으로 사용될 수 있다.The organic light emitting compound according to the present invention represented by the above [Formula I] can be used as various organic layers, including the electron transport layer in the organic light emitting device due to its structural specificity.
본 발명에 따른 [화학식 Ⅰ]로 표시되는 유기발광 화합물의 바람직한 구체예로는 하기 화합물들이 있으나, 이들에만 한정되는 것은 아니다.Preferred examples of the organic light emitting compound represented by [Formula I] according to the present invention include the following compounds, but is not limited thereto.
이와 같이, 본 발명에 따른 유기발광 화합물은 고유의 특성을 발휘하는 특징적인 골격과 이에 도입되는 고유의 특성을 갖는 모이어티 (moiety)를 이용하여 다양한 특성을 갖는 유기발광 화합물을 합성할 수 있고, 그 결과 본 발명에 따른 유기발광 화합물을 발광층, 정공수송층, 전자수송층, 전자저지층, 정공저지층 등 다양한 유기층 물질로 적용할 수 있고, 바람직하게는 전자수송 재료로 소자의 발광효율 등의 발광 특성을 더욱 향상시킬 수 있다.As such, the organic light emitting compound according to the present invention can synthesize an organic light emitting compound having various characteristics using a characteristic skeleton exhibiting unique properties and a moiety having intrinsic properties introduced thereto, As a result, the organic light emitting compound according to the present invention can be applied to various organic layer materials such as a light emitting layer, a hole transport layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. can be further improved.
또한, 본 발명의 화합물은 일반적인 유기발광소자 제조방법에 따라 소자에 적용할 수 있다.In addition, the compound of the present invention can be applied to a device according to a general method for manufacturing an organic light emitting device.
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.The organic light emitting device according to an embodiment of the present invention may have a structure including a first electrode and a second electrode and an organic layer disposed therebetween. Except that, it may be manufactured using a conventional device manufacturing method and material.
본 발명에 따른 유기발광소자의 유기층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층, 전자 저지층, 정공 저지층 등을 포함할 수 있으며, 유기발광소자에 구비되는 광효율 개선층 (Capping layer)을 포함하는 구조를 가질 수도 있으며, 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, but may have a multi-layered structure in which two or more organic layers are stacked. For example, it may include 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, etc., a structure including a light efficiency improving layer (Capping layer) provided in the organic light emitting device may have, but is not limited thereto, and may include a smaller number or a larger number of organic layers.
본 발명에 따른 바람직한 유기발광소자의 유기층 구조 등에 대해서는 후술하는 실시예에서 보다 상세하게 설명한다.The organic layer structure of the preferred organic light emitting device according to the present invention will be described in more detail in the following Examples.
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 PVD (physical vapor deposition) method, such as sputtering or e-beam evaporation, to form a metal or a conductive metal oxide or an alloy thereof on a substrate. It can be prepared 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 in a smaller number by a solvent process rather than a vapor deposition method using various polymer materials, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It 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 large 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, gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc. 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) , a conductive polymer such as polypyrrole and polyaniline, but is 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 to facilitate electron injection into the organic layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof, and multilayered materials such as LiF/Al or LiO 2 /Al Structural materials and the like, but are not limited thereto.
정공 주입 물질로는 낮은 전압에서 양극으로부터 정공을 잘 주입받을 수 있는 물질로서, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기층의 HOMO 사이인 것이 바람직하다. 정공 주입 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 well injecting holes from the anode at a low voltage, and it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is 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 material, hexanitrile hexaazatriphenylene, quinacridone-based organic material, perylene-based organic material, Anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.
정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송 받아 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, 본 발명에 따른 유기발광 화합물을 이용하여 소자의 저전압 구동 특성, 발광효율 및 수명 특성을 더욱 향상시킬 수 있다.As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is suitable, and a material having high hole mobility is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together. can be further improved.
발광 물질로는 정공 수송층과 전자 수송층으로부터 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, benzoxazole, benzthiazole and There are benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, rubrene, and the like, but is not limited thereto.
전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 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 is suitable, and a material having high electron mobility is suitable. Specific examples include, but are not limited to, an Al complex of 8-hydroxyquinoline, a complex including Alq 3 , an organic radical compound, and a hydroxyflavone-metal complex.
본 발명에 따른 유기발광소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting diode according to the present invention may be a top emission type, a back 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 can act on a principle similar to that applied to the organic light emitting device in organic electronic devices including organic solar cells, organic photoreceptors, organic transistors, and the like.
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 for explaining the present invention in more detail, the scope of the present invention is not limited thereby, and it is common in the art that various changes and modifications are possible within the scope and spirit of the present invention. It will be obvious to those with knowledge.
합성예Synthesis example 1 : 화합물 1의 합성 1: Synthesis of compound 1
(1) (One) 제조예production example 1 : 중간체 1-1의 합성 1: Synthesis of Intermediate 1-1
9-Bromo-7,7-dimethyl-7H-benzo[c]fluorene (10.0 g, 0.031 mol), Copper(I) cyanide (5.5 g, 0.062 mol)에 DMF 150 mL를 넣고 12시간 동안 150 ℃에서 환류 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 1-1>을 7.4 g (수율 88.8%) 수득하였다.Add 150 mL of DMF to 9-Bromo-7,7-dimethyl-7H-benzo[c]fluorene (10.0 g, 0.031 mol) and Copper(I) cyanide (5.5 g, 0.062 mol) and reflux at 150 °C for 12 hours. The reaction was stirred. After completion of the reaction, 7.4 g (yield 88.8%) of <Intermediate 1-1> was obtained by extraction, concentration, and column.
(2) (2) 제조예production example 2 : 중간체 1-2의 합성 2: Synthesis of intermediate 1-2
중간체 1-1 (10.0 g, 0.037 mol), N-Bromosuccinimide (7.9 g, 0.045 mol)에 DMF 180 mL를 넣고 6시간 동안 상온에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 1-2>를 9.1 g (수율 70.4%) 수득하였다.180 mL of DMF was added to Intermediate 1-1 (10.0 g, 0.037 mol) and N-Bromosuccinimide (7.9 g, 0.045 mol), and the reaction was stirred at room temperature for 6 hours. After completion of the reaction, 9.1 g (yield 70.4%) of <Intermediate 1-2> was obtained by extraction and concentration, followed by column and recrystallization.
(3) (3) 제조예production example 3 : 중간체 1-3의 합성 3: Synthesis of Intermediate 1-3
중간체 1-2 (10.0 g, 0.029 mol), Bis(pinacolato)diboron (8.8 g, 0.035 mol), KOAc (5.6 g, 0.057 mol), Pd(dppf)Cl2 (0.6 g, 0.001 mol)에 dioxane 200 mL 넣고 100 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 1-3>을 8.3 g (수율 73.1%) 수득하였다.Intermediate 1-2 (10.0 g, 0.029 mol), Bis(pinacolato)diboron (8.8 g, 0.035 mol), KOAc (5.6 g, 0.057 mol), Pd(dppf)Cl 2 (0.6 g, 0.001 mol) in dioxane 200 mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 8.3 g (yield 73.1%) of <Intermediate 1-3>.
(4) (4) 제조예production example 4 : 화합물 1의 합성 4: Synthesis of compound 1
2-Chloro-4,6-diphenyl-1,3,5-triazine (10.0 g, 0.037 mol), 중간체 1-3 (17.7 g, 0.045 mol), K2CO3 (15.5 g, 0.112 mol), Pd(PPh3)4 (0.9 g, 0.001 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 1>을 13.3 g (수율 71.1%) 수득하였다.2-Chloro-4,6-diphenyl-1,3,5-triazine (10.0 g, 0.037 mol), Intermediate 1-3 (17.7 g, 0.045 mol), K 2 CO 3 (15.5 g, 0.112 mol), Pd 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added to (PPh 3 ) 4 (0.9 g, 0.001 mol) and stirred at 100 °C for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 13.3 g (yield 71.1%) of <Compound 1>.
LC/MS: m/z=500[(M+1)+]LC/MS: m/z=500[(M+1) + ]
합성예Synthesis example 2 : 화합물 4의 합성 2: Synthesis of compound 4
(1) (One) 제조예production example 1 : 화합물 4의 합성 1: Synthesis of compound 4
2,4-Bis(4-biphenylyl)-6-chloro-1,3,5-triazine (10.0 g, 0.024 mol), 중간체 1-3 (11.3 g, 0.029 mol), K2CO3 (9.9 g, 0.071 mol), Pd(PPh3)4 (0.6 g, 0.001 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 4>를 11.5 g (수율 73.9%) 수득하였다.2,4-Bis(4-biphenylyl)-6-chloro-1,3,5-triazine (10.0 g, 0.024 mol), Intermediate 1-3 (11.3 g, 0.029 mol), K 2 CO 3 (9.9 g, 0.071 mol), Pd(PPh 3 ) 4 (0.6 g, 0.001 mol) was added with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O, followed by stirring at 100° C. for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 11.5 g (yield 73.9%) of <Compound 4>.
LC/MS: m/z=652[(M+1)+]LC/MS: m/z=652 [(M+1) + ]
합성예Synthesis example 3 : 화합물 6의 합성 3: Synthesis of compound 6
(1) (One) 제조예production example 1 : 중간체 6-1의 합성 1: Synthesis of Intermediate 6-1
Cyanuric chloride (10.0 g, 0.054 mol), 9-Phenanthracenylboronic acid (28.9 g, 0.130 mol), K2CO3 (44.9 g, 0.325 mol), Pd(PPh3)4 (1.2 g, 0.001 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 6-1>을 17.3 g (수율 68.2%) 수득하였다.Cyanuric chloride (10.0 g, 0.054 mol), 9-Phenanthracenylboronic acid (28.9 g, 0.130 mol), K 2 CO 3 (44.9 g, 0.325 mol), Pd(PPh 3 ) 4 (1.2 g, 0.001 mol) toluene 200 mL, 50 mL of ethanol, and 50 mL of H 2 O were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 17.3 g (yield 68.2%) of <Intermediate 6-1>.
(2) (2) 제조예production example 2 : 화합물 6의 합성 2: Synthesis of compound 6
중간체 6-1 (10.0 g, 0.015 mol), 중간체 1-3 (10.1 g, 0.019 mol), K2CO3 (6.4 g, 0.046 mol), Pd(PPh3)4 (0.4 g, 0.001 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 6>을 7.5 g (수율 69.3%) 수득하였다.To Intermediate 6-1 (10.0 g, 0.015 mol), Intermediate 1-3 (10.1 g, 0.019 mol), K 2 CO 3 (6.4 g, 0.046 mol), Pd(PPh 3 ) 4 (0.4 g, 0.001 mol) 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.5 g (yield 69.3%) of <Compound 6>.
LC/MS: m/z=700[(M+1)+]LC/MS: m/z=700[(M+1) + ]
합성예Synthesis example 4 : 화합물 29의 합성 4: Synthesis of compound 29
(1) (One) 제조예production example 1 : 화합물 29의 합성 1: Synthesis of compound 29
2-(4-Bromophenyl)-4,6-di(naphthalen-2-yl)-1,3,5-triazine (10.0 g, 0.021 mol), 중간체 1-3 (9.7 g, 0.025 mol), K2CO3 (8.5 g, 0.061 mol), Pd(PPh3)4 (0.5 g, 0.0004 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 29>를 9.8 g (수율 70.7%) 수득하였다.2-(4-Bromophenyl)-4,6-di(naphthalen-2-yl)-1,3,5-triazine (10.0 g, 0.021 mol), Intermediate 1-3 (9.7 g, 0.025 mol), K 2 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added to CO 3 (8.5 g, 0.061 mol), Pd(PPh 3 ) 4 (0.5 g, 0.0004 mol), and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 9.8 g (yield 70.7%) of <Compound 29>.
LC/MS: m/z=676[(M+1)+]LC/MS: m/z=676[(M+1) + ]
합성예Synthesis example 5 : 화합물 31의 합성 5: Synthesis of compound 31
(1) (One) 제조예production example 1 : 화합물 31의 합성 1: Synthesis of compound 31
2-(4-Bromophenyl)-4,6-di(naphthalen-1-yl)-1,3,5-triazine (10.0 g, 0.021 mol), 중간체 1-3 (9.7 g, 0.025 mol), K2CO3 (8.5 g, 0.061 mol), Pd(PPh3)4 (0.5 g, 0.0004 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 31>을 9.6 g (수율 69.3%) 수득하였다.2-(4-Bromophenyl)-4,6-di(naphthalen-1-yl)-1,3,5-triazine (10.0 g, 0.021 mol), Intermediate 1-3 (9.7 g, 0.025 mol), K 2 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added to CO 3 (8.5 g, 0.061 mol), Pd(PPh 3 ) 4 (0.5 g, 0.0004 mol), and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 9.6 g (yield 69.3%) of <Compound 31>.
LC/MS: m/z=676[(M+1)+]LC/MS: m/z=676[(M+1) + ]
합성예Synthesis example 6 : 화합물 39의 합성 6: Synthesis of compound 39
(1) (One) 제조예production example 1 : 중간체 39-1의 합성 1: Synthesis of intermediate 39-1
1-Bromo-4-iodobenzene (10.0 g, 0.035 mol), 중간체 1-3 (16.8 g, 0.042 mol), K2CO3 (14.7 g, 0.106 mol), Pd(PPh3)4 (0.8 g, 0.001 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 39-1>을 7.9 g (수율 52.7%) 수득하였다.1-Bromo-4-iodobenzene (10.0 g, 0.035 mol), Intermediate 1-3 (16.8 g, 0.042 mol), K 2 CO 3 (14.7 g, 0.106 mol), Pd(PPh 3 ) 4 (0.8 g, 0.001) mol) was added 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O, and stirred at 100 °C for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column to obtain 7.9 g (yield: 52.7%) of <Intermediate 39-1>.
(2) (2) 제조예production example 2 : 중간체 39-2의 합성 2: Synthesis of intermediate 39-2
중간체 39-1 (10.0 g, 0.024 mol), Bis(pinacolato)diboron (7.2 g, 0.028 mol), KOAc (4.6 g, 0.047 mol), Pd(dppf)Cl2 (0.5 g, 0.001 mol)에 dioxane 200 mL 넣고 100 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 39-2>를 7.9 g (수율 71.1%) 수득하였다.Intermediate 39-1 (10.0 g, 0.024 mol), Bis(pinacolato)diboron (7.2 g, 0.028 mol), KOAc (4.6 g, 0.047 mol), Pd(dppf)Cl 2 (0.5 g, 0.001 mol) in dioxane 200 mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, extraction and concentration were performed, and then column <Intermediate 39-2> was obtained to obtain 7.9 g (yield 71.1%).
(3) (3) 제조예production example 3 : 중간체 39-3의 합성 3: Synthesis of intermediate 39-3
Cyanuric chloride (10.0 g, 0.054 mol), 4-(2-Benzo[d]oxazolyl)phenylboronic acid (31.1 g, 0.130 mol), K2CO3 (44.9 g, 0.325 mol), Pd(PPh3)4 (1.3 g, 0.001 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 39-3>을 17.2 g (수율 63.2%) 수득하였다.Cyanuric chloride (10.0 g, 0.054 mol), 4-(2-Benzo[d]oxazolyl)phenylboronic acid (31.1 g, 0.130 mol), K 2 CO 3 (44.9 g, 0.325 mol), Pd(PPh 3 ) 4 ( 1.3 g, 0.001 mol) was added to 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 17.2 g (yield: 63.2%) of <Intermediate 39-3>.
(4) (4) 제조예production example 4 : 화합물 39의 합성 4: Synthesis of compound 39
중간체 39-3 (10.0 g, 0.020 mol), 중간체 39-2 (11.3 g, 0.024 mol), K2CO3 (8.3 g, 0.060 mol), Pd(PPh3)4 (0.5 g, 0.001 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 39>를 11.2 g (수율 69.3%) 수득하였다.To intermediate 39-3 (10.0 g, 0.020 mol), intermediate 39-2 (11.3 g, 0.024 mol), K 2 CO 3 (8.3 g, 0.060 mol), Pd(PPh 3 ) 4 (0.5 g, 0.001 mol) 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 11.2 g (yield: 69.3%) of <Compound 39>.
LC/MS: m/z=810[(M+1)+]LC/MS: m/z=810[(M+1) + ]
합성예Synthesis example 7 : 화합물 45의 합성 7: Synthesis of compound 45
(1) (One) 제조예production example 1 : 화합물 45의 합성 1: Synthesis of compound 45
4,6-Diphenyl-1,3,5-triazine (10.0 g, 0.026 mol), 중간체 39-2 (14.6 g, 0.031 mol), K2CO3 (10.7 g, 0.077 mol), Pd(PPh3)4 (0.6 g, 0.001 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 45>를 12.4 g (수율 73.8%) 수득하였다.4,6-Diphenyl-1,3,5-triazine (10.0 g, 0.026 mol), intermediate 39-2 (14.6 g, 0.031 mol), K 2 CO 3 (10.7 g, 0.077 mol), Pd(PPh 3 ) 4 (0.6 g, 0.001 mol) was added with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 12.4 g (yield 73.8%) of <Compound 45>.
LC/MS: m/z=652[(M+1)+]LC/MS: m/z=652 [(M+1) + ]
합성예Synthesis example 8 : 화합물 116의 합성 8: Synthesis of compound 116
(1) (One) 제조예production example 1 : 중간체 116-1의 합성 1: Synthesis of intermediate 116-1
2,7-Dibromo-9,9-dimethyl-9H-fluorene (10.0 g, 0.028 mol), 중간체 1-3 (13.5 g, 0.034 mol), K2CO3 (11.8 g, 0.085 mol), Pd(PPh3)4 (0.7 g, 0.001 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 116-1>을 8.1 g (수율 52.8%) 수득하였다.2,7-Dibromo-9,9-dimethyl-9H-fluorene (10.0 g, 0.028 mol), Intermediate 1-3 (13.5 g, 0.034 mol), K 2 CO 3 (11.8 g, 0.085 mol), Pd(PPh) 3 ) 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added to 4 (0.7 g, 0.001 mol) and stirred at 100 °C for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 8.1 g (yield 52.8%) of <Intermediate 116-1>.
(2) (2) 제조예production example 2 : 중간체 116-2의 합성 2: Synthesis of intermediate 116-2
중간체 116-1 (10.0 g, 0.019 mol), Bis(pinacolato)diboron (5.6 g, 0.022 mol), KOAc (3.6 g, 0.037 mol), Pd(dppf)Cl2 (0.4 g, 0.001 mol)에 dioxane 200 mL 넣고 100 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 116-2>를 7.8 g (수율 71.8%) 수득하였다.Intermediate 116-1 (10.0 g, 0.019 mol), Bis(pinacolato)diboron (5.6 g, 0.022 mol), KOAc (3.6 g, 0.037 mol), dioxane 200 in Pd(dppf)Cl 2 (0.4 g, 0.001 mol) mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column to obtain 7.8 g (yield 71.8%) of <Intermediate 116-2>.
(3) (3) 제조예production example 3 : 화합물 116의 합성 3: Synthesis of compound 116
중간체 116-2 (10.0 g, 0.017 mol), 2-Chloro-4,6-diphenyl-1,3,5-triazine (5.5 g, 0.020 mol), K2CO3 (7.1 g, 0.051 mol), Pd(PPh3)4 (0.4 g, 0.001 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 116>을 8.8 g (수율 74.6%) 수득하였다.Intermediate 116-2 (10.0 g, 0.017 mol), 2-Chloro-4,6-diphenyl-1,3,5-triazine (5.5 g, 0.020 mol), K 2 CO 3 (7.1 g, 0.051 mol), Pd 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added to (PPh 3 ) 4 (0.4 g, 0.001 mol), and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 8.8 g (yield 74.6%) of <Compound 116>.
LC/MS: m/z=692[(M+1)+]LC/MS: m/z=692[(M+1) + ]
합성예Synthesis example 9 : 화합물 138의 합성 9: Synthesis of compound 138
(1) (One) 제조예production example 1 : 중간체 138-1의 합성 1: Synthesis of intermediate 138-1
4,6-Dibromodibenzofuran (10.0 g, 0.031 mol), 중간체 1-3 (14.6 g, 0.037 mol), K2CO3 (12.7 g, 0.092 mol), Pd(PPh3)4 (0.7 g, 0.001 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 138-1>을 8.5 g (수율 53.9%) 수득하였다.4,6-Dibromodibenzofuran (10.0 g, 0.031 mol), Intermediate 1-3 (14.6 g, 0.037 mol), K 2 CO 3 (12.7 g, 0.092 mol), Pd(PPh 3 ) 4 (0.7 g, 0.001 mol) 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added thereto, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 8.5 g (yield 53.9%) of <Intermediate 138-1>.
(2) (2) 제조예production example 2 : 중간체 138-2의 합성 2: Synthesis of intermediate 138-2
중간체 138-1 (10.0 g, 0.019 mol), Bis(pinacolato)diboron (5.9 g, 0.023 mol), KOAc (3.8 g, 0.039 mol), Pd(dppf)Cl2 (0.4 g, 0.001 mol)에 dioxane 200 mL 넣고 100 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 138-2>를 8.2 g (수율 75.1%) 수득하였다.Intermediate 138-1 (10.0 g, 0.019 mol), Bis(pinacolato)diboron (5.9 g, 0.023 mol), KOAc (3.8 g, 0.039 mol), dioxane 200 in Pd(dppf)Cl 2 (0.4 g, 0.001 mol) mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, extraction and concentration were performed to obtain 8.2 g (yield 75.1%) of <Intermediate 138-2>.
(3) (3) 제조예production example 3 : 화합물 138의 합성 3: Synthesis of compound 138
중간체 138-2 (10.0 g, 0.018 mol), 2-Chloro-4,6-diphenyl-1,3,5-triazine (5.7 g, 0.021 mol), K2CO3 (7.4 g, 0.053 mol), Pd(PPh3)4 (0.4 g, 0.0004 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 138>을 7.8 g (수율 75.7%) 수득하였다.Intermediate 138-2 (10.0 g, 0.018 mol), 2-Chloro-4,6-diphenyl-1,3,5-triazine (5.7 g, 0.021 mol), K 2 CO 3 (7.4 g, 0.053 mol), Pd 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added to (PPh 3 ) 4 (0.4 g, 0.0004 mol), and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.8 g (yield 75.7%) of <Compound 138>.
LC/MS: m/z=666[(M+1)+]LC/MS: m/z=666[(M+1) + ]
합성예Synthesis example 10 : 화합물 151의 합성 10: Synthesis of compound 151
(1) (One) 제조예production example 1 : 중간체 151-1의 합성 1: Synthesis of intermediate 151-1
4-Bromo-2-naphthol (10.0 g, 0.045 mol), KI (5.2 g, 0.031 mol), KIO3 (2.88 g, 0.130 mol)에 H2O 375 mL, H2SO4 8 mL 넣고 상온에서 18시간 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 151-1>을 7.6 g (수율 48.7%) 수득하였다.To 4-Bromo-2-naphthol (10.0 g, 0.045 mol), KI (5.2 g, 0.031 mol), KIO 3 (2.88 g, 0.130 mol), add 375 mL of H 2 O, 8 mL of H 2 SO 4 and 18 at room temperature. time was reacted. After completion of the reaction, 7.6 g (yield 48.7%) of <Intermediate 151-1> was obtained by extraction, concentration, and column.
(2) (2) 제조예production example 2 : 중간체 151-2의 합성 2: Synthesis of intermediate 151-2
중간체 151-1 (10.0 g, 0.029 mol), K2CO3 (5.5 g, 0.040 mol)에 Acetone 66 mL 넣고 Dimethyl sulfate (4.7 g, 0.037 mol)를 천천히 적가한 후, 55 ℃에서 1시간 동안 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 151-2>를 9.5 g (수율 91.3%) 수득하였다.Intermediate 151-1 (10.0 g, 0.029 mol), K 2 CO 3 (5.5 g, 0.040 mol) was added with 66 mL of Acetone, slowly added dropwise dimethyl sulfate (4.7 g, 0.037 mol), and stirred at 55 °C for 1 hour. and reacted. After completion of the reaction, 9.5 g (yield 91.3%) of <Intermediate 151-2> was obtained by extraction, concentration, and column.
(3) (3) 제조예production example 3 : 중간체 151-3의 합성 3: Synthesis of intermediate 151-3
중간체 151-2 (10.0 g, 0.028 mol), 4-Chloro-2-fluorophenylboronic acid (5.8 g, 0.033 mol), K2CO3 (11.4 g, 0.083 mol), Pd(PPh3)4 (0.6 g, 0.006 mol)에 Toluene 140 mL, EtOH 35 mL, H2O 35 mL 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 151-3>을 7.9 g (수율 51.2%) 수득하였다.Intermediate 151-2 (10.0 g, 0.028 mol), 4-Chloro-2-fluorophenylboronic acid (5.8 g, 0.033 mol), K 2 CO 3 (11.4 g, 0.083 mol), Pd(PPh 3 ) 4 (0.6 g, 0.006 mol) into 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H 2 O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, 7.9 g (yield 51.2%) of <Intermediate 151-3> was obtained by extraction, concentration, and column.
(4) (4) 제조예production example 4 : 중간체 151-4의 합성 4: Synthesis of intermediate 151-4
중간체 151-3 (10.0 g, 0.027 mol)을 anhydrous DCM에 용해시키고, BBr3 (in DCM) (17.13 g, 0.068 mol)를 0 ℃에서 dropwise로 적가하였다. 상온에서 16시간 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 151-4>를 8.2 g (수율 85.3%) 수득하였다.Intermediate 151-3 (10.0 g, 0.027 mol) was dissolved in anhydrous DCM, and BBr 3 (in DCM) (17.13 g, 0.068 mol) was added dropwise at 0 °C dropwise. The reaction was stirred at room temperature for 16 hours. After completion of the reaction, 8.2 g (yield 85.3%) of <Intermediate 151-4> was obtained by extraction, concentration, and column.
(5) (5) 제조예production example 5 : 중간체 151-5의 합성 5: Synthesis of intermediate 151-5
중간체 151-4 (10.0 g, 0.030 mol), K2CO3 (10.3 g, 0.043 mol)에 NMP 500 mL 넣고 180 ℃에서 24시간 동안 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 151-5>를 5.0 g (수율 53.0%) 수득하였다.Intermediate 151-4 (10.0 g, 0.030 mol), K 2 CO 3 (10.3 g, 0.043 mol) NMP 500 mL was added to the reaction was stirred at 180 ℃ for 24 hours. After completion of the reaction, 5.0 g (yield 53.0%) of <Intermediate 151-5> was obtained by extraction, concentration, and column.
(6) (6) 제조예production example 6 : 중간체 151-6의 합성 6: Synthesis of intermediate 151-6
중간체 151-5 (10.0 g, 0.030 mol), Bis(pinacolato)diboron (9.2 g, 0.036 mol), KOAc (5.9 g, 0.060 mol), Pd(dppf)Cl2 (0.7 g, 0.001 mol)에 dioxane 200 mL 넣고 100 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 151-6>을 7.7 g (수율 67.4%) 수득하였다.Intermediate 151-5 (10.0 g, 0.030 mol), Bis(pinacolato)diboron (9.2 g, 0.036 mol), KOAc (5.9 g, 0.060 mol), dioxane 200 in Pd(dppf)Cl 2 (0.7 g, 0.001 mol) mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column to obtain 7.7 g (yield 67.4%) of <Intermediate 151-6>.
(7) (7) 제조예production example 7 : 중간체 151-7의 합성 7: Synthesis of intermediate 151-7
2-Chloro-4,6-diphenyl-1,3,5-triazine (10.0 g, 0.037 mol), 중간체 151-6 (16.9 g, 0.045 mol), K2CO3 (15.5 g, 0.112 mol), Pd(PPh3)4 (0.9 g, 0.001 mol)에 toluene 200 ml, ethanol 50 ml, H2O 50 ml를 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 151-7>을 11.5 g (수율 63.6%) 수득하였다.2-Chloro-4,6-diphenyl-1,3,5-triazine (10.0 g, 0.037 mol), Intermediate 151-6 (16.9 g, 0.045 mol), K 2 CO 3 (15.5 g, 0.112 mol), Pd 200 ml of toluene, 50 ml of ethanol, and 50 ml of H 2 O were added to (PPh 3 ) 4 (0.9 g, 0.001 mol) and stirred at 100° C. for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 11.5 g (yield 63.6%) of <Intermediate 151-7>.
(8) (8) 제조예production example 8 : 화합물 151의 합성 8: Synthesis of compound 151
중간체 151-7 (10.0 g, 0.021 mol), Pd(OAc)2 (0.07 g, 0.0003 mol), X-Phos (0.3 g, 0.0006 mol), K4[Fe(CN)6]·3H2O (0.55 g, 0.0013 mol), K2CO3 (0.7 g, 0.005 mol)에 1:1로 혼합한 water/1,4 dioxane을 넣고 상온에서 10시간 동안 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 151>을 7.1 g (수율 72.4%) 수득하였다.Intermediate 151-7 (10.0 g, 0.021 mol), Pd(OAc) 2 (0.07 g, 0.0003 mol), X-Phos (0.3 g, 0.0006 mol), K 4 [Fe(CN) 6 ] 3H 2 O ( 0.55 g, 0.0013 mol), water/1,4 dioxane mixed 1:1 with K 2 CO 3 (0.7 g, 0.005 mol) was added, and the reaction was stirred at room temperature for 10 hours. After completion of the reaction, 7.1 g (yield 72.4%) of <Compound 151> was obtained by extraction and concentration, followed by column and recrystallization.
LC/MS: m/z=474[(M+1)+]LC/MS: m/z=474[(M+1) + ]
합성예Synthesis example 11 : 화합물 156의 합성 11: Synthesis of compound 156
(1) (One) 제조예production example 1 : 중간체 156-1의 합성 1: Synthesis of Intermediate 156-1
2-(4-Chlorophenyl)-4,6-diphenyl-1,3,5-triazine (10.0 g, 0.029 mol), 중간체 151-6 (13.2 g, 0.035 mol), K2CO3 (12.1 g, 0.087 mol), Pd(PPh3)4 (0.7 g, 0.001 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 100 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 156-1>을 9.8 g (수율 60.2%) 수득하였다.2-(4-Chlorophenyl)-4,6-diphenyl-1,3,5-triazine (10.0 g, 0.029 mol), intermediate 151-6 (13.2 g, 0.035 mol), K 2 CO 3 (12.1 g, 0.087) mol), Pd(PPh 3 ) 4 (0.7 g, 0.001 mol) was added with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O, followed by stirring at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 9.8 g (yield: 60.2%) of <Intermediate 156-1>.
(2) (2) 제조예production example 2 : 화합물 156의 합성 2: Synthesis of compound 156
중간체 156-1 (10.0 g, 0.018 mol), Pd(OAc)2 (0.06 g, 0.0003 mol), X-Phos (0.26 g, 0.0005 mol), K4[Fe(CN)6]·3H2O (0.47 g, 0.0011 mol), K2CO3 (0.62 g, 0.004 mol)에 1:1로 혼합한 water/1,4 dioxane을 넣고 상온에서 10시간 동안 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 156>을 7.1 g (수율 72.2%) 수득하였다.Intermediate 156-1 (10.0 g, 0.018 mol), Pd(OAc) 2 (0.06 g, 0.0003 mol), X-Phos (0.26 g, 0.0005 mol), K 4 [Fe(CN) 6 ] 3H 2 O ( 0.47 g, 0.0011 mol), water/1,4 dioxane mixed 1:1 with K 2 CO 3 (0.62 g, 0.004 mol) was added, and the reaction was stirred at room temperature for 10 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.1 g (yield 72.2%) of <Compound 156>.
LC/MS: m/z=550[(M+1)+]LC/MS: m/z=550[(M+1) + ]
소자 실시예 (ETL)Device Example (ETL)
본 발명에 따른 실시예에서, ITO 투명 전극은 25 mm × 25 mm × 0.7 mm의 유리 기판 위에, ITO 투명 전극이 부착된 ITO 유리 기판을 이용하여, 발광 면적이 2 mm × 2 mm 크기가 되도록 패터닝한 후 세정하였다. 기판을 진공 챔버에 장착한 후 베이스 압력이 1 × 10-6 torr 이상 되도록 한 후 유기물을 상기 ITO 위에 하기 구조로 유기물과 금속을 증착하였다.In an embodiment according to the present invention, the ITO transparent electrode is patterned so that the light emitting area is 2 mm × 2 mm in size, using an ITO glass substrate to which an ITO transparent electrode is attached, on a glass substrate of 25 mm × 25 mm × 0.7 mm After that, it was washed. After the substrate was mounted in a vacuum chamber and the base pressure was set to 1 × 10 -6 torr or more, the organic material and the metal were deposited on the ITO in the following structure.
소자 실시예 1 내지 30Device Examples 1 to 30
본 발명에 따라 구현되는 화합물을 전자수송층으로 사용하였다. 하기와 같은 소자 구조를 갖는 청색 유기발광소자를 제작하여, 전류 효율을 포함한 발광 특성을 측정하였다. The compound implemented according to the present invention was used as the electron transport layer. A blue organic light emitting device having the following device structure was fabricated, and light emitting characteristics including current efficiency were measured .
ITO / 정공주입층 (HAT-CN, 5 nm) / 정공수송층 (α-NPB, 100 nm) / 전자저지층 (EBL1 10 nm) / 발광층 (20 nm) / 정공저지층 (HBL1, 50 nm) / 전자수송층 (201:Liq, 30 nm) / LiF (1 nm) / Al (100 nm)ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (α-NPB, 100 nm) / electron blocking layer (EBL1 10 nm) / light emitting layer (20 nm) / hole blocking layer (HBL1, 50 nm) / Electron transport layer (201:Liq, 30 nm) / LiF (1 nm) / Al (100 nm)
ITO 투명 전극에 정공주입층을 형성하기 위해 [HAT-CN]을 이용하여 5 nm로 증착하고, 이후 정공수송층은 α-NPB를 사용하여 100 nm 성막하였다. 전자저지층은 [EBL1]을 사용하여 10 nm의 두께로 증착하였다. 또한, 발광층에는 호스트 화합물로 [BH1]을 사용하고, 도판트 화합물은 [BD1]을 사용하여 두께가 20 nm 되도록 공증착하였다. 전자수송층은 본 발명으로 구현되는 화합물 화학식 1, 4, 6, 7, 9, 24, 26, 39, 45, 48, 115, 116, 117, 118, 122, 124, 125, 131, 133, 138, 143, 144, 145, 146, 148, 150, 151, 155, 156, 190을 사용하여 30 nm (Liq 도핑) 두께로 성막하였다. LiF 1 nm 및 Al 100 nm를 성막하여 유기발광소자를 제작하였다.To form a hole injection layer on the ITO transparent electrode, [HAT-CN] was used to deposit 5 nm, and then, the hole transport layer was deposited at 100 nm using α-NPB. The electron blocking layer was deposited to a thickness of 10 nm using [EBL1]. In addition, [BH1] was used as the host compound for the light emitting layer, and [BD1] was used as the dopant compound to be co-deposited to a thickness of 20 nm. The electron transport layer is a compound of Formula 1, 4, 6, 7, 9, 24, 26, 39, 45, 48, 115, 116, 117, 118, 122, 124, 125, 131, 133, 138, 143, 144, 145, 146, 148, 150, 151, 155, 156, and 190 were used to form a film to a thickness of 30 nm (Liq doping). An organic light emitting device was manufactured by forming a film of 1 nm LiF and 100 nm of Al.
소자 비교예 1Device Comparative Example 1
소자 비교예 1을 위한 유기발광소자는 상기 실시예 1의 소자구조에서 전자수송층을 본 발명으로 구현되는 화합물 대신에 하기 201을 사용한 것을 제외하고 동일하게 제작하였다.The organic light emitting device for Device Comparative Example 1 was manufactured in the same manner except that 201 was used instead of the compound embodied in the present invention for the electron transport layer in the device structure of Example 1.
소자 비교예 2Device Comparative Example 2
소자 비교예 2를 위한 유기발광소자는 상기 실시예 1의 소자구조에서 전자수송층을 본 발명으로 구현되는 화합물 대신에 하기 ET1을 사용한 것을 제외하고 동일하게 제작하였다.The organic light emitting device for Device Comparative Example 2 was manufactured in the same manner except that ET1 was used instead of the compound embodied in the present invention for the electron transport layer in the device structure of Example 1.
소자 비교예 3Device Comparative Example 3
소자 비교예 3을 위한 유기발광소자는 상기 실시예 1의 소자구조에서 전자수송층을 본 발명으로 구현되는 화합물 대신에 하기 ET2를 사용한 것을 제외하고 동일하게 제작하였다.The organic light emitting device for Device Comparative Example 3 was manufactured in the same manner except that ET2 was used instead of the compound embodied in the present invention for the electron transport layer in the device structure of Example 1.
소자 비교예 4Device Comparative Example 4
소자 비교예 4를 위한 유기발광소자는 상기 실시예 1의 소자구조에서 전자수송층을 본 발명으로 구현되는 화합물 대신에 ET3을 사용한 것을 제외하고 동일하게 제작하였다.The organic light emitting device for Device Comparative Example 4 was manufactured in the same manner except that ET3 was used instead of the compound embodied in the present invention for the electron transport layer in the device structure of Example 1.
실험예 1 : 소자 실시예 1 내지 30의 발광 특성Experimental Example 1: Light emitting characteristics of Device Examples 1 to 30
상기 실시예에 따라 제조된 유기발광소자는 Source meter (Model 237, Keithley)와 휘도계 (PR-650, Photo Research)를 이용하여 전압, 전류 및 발광 효율을 측정하였고, 1000 nit 기준의 결과값은 하기 [표 1]과 같다.The organic light emitting device manufactured according to the above Example was measured for voltage, current and luminous efficiency using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), and the result value based on 1000 nit was It is shown in [Table 1] below.
상기 [표 1]에 나타낸 결과를 살펴보면, 본 발명에 따른 화합물을 유기발광소자 내의 전자수송층에 적용한 경우 종래의 화합물 및 본 발명에 따른 특징적 구조를 갖지 않는 화합물을 채용한 소자 (비교예 1 내지 4)에 비하여 저전압 구동 특성, 발광 효율, 양자 효율 등 발광 특성이 현저히 우수함을 확인할 수 있다.Looking at the results shown in [Table 1], when the compound according to the present invention is applied to the electron transport layer in the organic light emitting device, a device employing a conventional compound and a compound having no characteristic structure according to the present invention (Comparative Examples 1 to 4) ), it can be seen that the luminescence characteristics such as low voltage driving characteristics, luminous efficiency, and quantum efficiency are significantly superior.
[HAT_CN] [α-NPB] [BH1] [BD1] [EBL1][HAT_CN] [α-NPB] [BH1] [BD1] [EBL1]
[201] [ET1] [ET2] [ET3][201] [ET1] [ET2] [ET3]
Claims (6)
[화학식 Ⅰ]
상기 [화학식 Ⅰ]에서,
X는 O, S 또는 C(CH3)2이고,
L은 단일결합이거나, 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴렌기 중에서 선택되고 (n은 0 내지 3의 정수이고, n이 2 이상인 경우 복수 개의 L은 서로 동일하거나 상이함),
Ar1 내지 Ar2는 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기 중에서 선택되며,
CN은 시아노기 (cyano group)를 의미한다.An organic light emitting compound represented by the following [Formula I]:
[Formula Ⅰ]
In the [Formula I],
X is O, S or C(CH 3 ) 2 ,
L is a single bond, or is selected from a substituted or unsubstituted C6 to C30 arylene group and a substituted or unsubstituted C3 to C30 heteroarylene group (n is an integer from 0 to 3, and n is 2 or more a plurality of L's are the same or different from each other),
Ar 1 To Ar 2 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, a substituted or unsubstituted C It is selected from an aryl group having 6 to 30 and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,
CN means a cyano group.
상기 L, Ar1 내지 Ar2의 정의에서, '치환 또는 비치환된'이라 함은 L, Ar1 내지 Ar2가 각각 중수소, 할로겐기, 시아노기, 니트로기, 히드록시기, 실릴기, 알킬기, 할로겐화된 알킬기, 중수소화된 알킬기, 시클로알킬기, 헤테로시클로알킬기, 알콕시기, 할로겐화된 알콕시기, 중수소화된 알콕시기, 아릴기, 헤테로아릴기, 알킬아민기, 아릴아민기 및 실릴기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되거나, 상기 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것인 것을 특징으로 하는 유기발광 화합물.The method of claim 1,
In the definition of L, Ar 1 to Ar 2 , 'substituted or unsubstituted' means that L and Ar 1 to Ar 2 are deuterium, a halogen group, a cyano group, a nitro group, a hydroxy group, a silyl group, an alkyl group, a halogenated selected from the group consisting of an alkyl group, a deuterated 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 alkylamine group, an arylamine group and a silyl group. An organic light-emitting compound, characterized in that it is substituted with one or two or more substituents, or is substituted with a substituent to which two or more of the substituents are connected, or does not have any substituents.
상기 [화학식 Ⅰ]은 하기 [화합물 1] 내지 [화합물 190] 중에서 선택되는 어느 하나인 것을 특징으로 하는 유기발광 화합물:
The method of claim 1,
The [Formula I] is an organic light emitting compound, characterized in that any one selected from the following [Compound 1] to [Compound 190]:
상기 유기층 중 1 층 이상은 제1항에 따른 [화학식 Ⅰ]의 유기발광 화합물을 포함하는 것인 유기발광소자.An organic light emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode,
At least one of the organic layers is an organic light emitting device comprising the organic light emitting compound of [Formula I] according to claim 1.
상기 유기층은 정공 주입층, 정공 수송층, 정공 주입과 정공 수송 기능을 동시에 하는 층, 전자 수송층, 전자 주입층, 전자 수송과 전자 주입 기능을 동시에 하는 층, 전자 저지층, 정공 저지층 및 발광층 중에서 선택되는 1층 이상을 포함하고,
상기 층들 중 1층 이상이 상기 [화학식 Ⅰ]로 표시되는 유기발광 화합물을 포함하는 것을 특징으로 하는 유기발광소자.5. The method of claim 4,
The organic layer is selected from a hole injection layer, a hole transport layer, a layer that performs both hole injection and hole transport functions, an electron transport layer, an electron injection layer, a layer that performs both electron transport and electron injection functions, an electron blocking layer, a hole blocking layer and a light emitting layer including one or more floors that become
At least one of the layers comprises an organic light emitting compound represented by the [Formula I].
상기 전자 수송층, 전자 주입층 및 전자 수송과 전자 주입 기능을 동시에 하는 층 중 어느 하나에 상기 [화학식 Ⅰ]로 표시되는 유기발광 화합물을 포함하는 것을 특징으로 하는 유기발광소자.6. The method of claim 5,
An organic light emitting device comprising an organic light emitting compound represented by the above [Formula I] in any one of the electron transport layer, the electron injection layer, and the layer that performs both electron transport and electron injection functions.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020200174143A KR20220084559A (en) | 2020-12-14 | 2020-12-14 | An electroluminescent compound and an electroluminescent device comprising the same |
PCT/KR2021/016686 WO2022131575A1 (en) | 2020-12-14 | 2021-11-16 | Organic compound and organic light-emitting device comprising same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020200174143A KR20220084559A (en) | 2020-12-14 | 2020-12-14 | An electroluminescent compound and an electroluminescent device comprising the same |
Publications (1)
Publication Number | Publication Date |
---|---|
KR20220084559A true KR20220084559A (en) | 2022-06-21 |
Family
ID=82057884
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020200174143A KR20220084559A (en) | 2020-12-14 | 2020-12-14 | An electroluminescent compound and an electroluminescent device comprising the same |
Country Status (2)
Country | Link |
---|---|
KR (1) | KR20220084559A (en) |
WO (1) | WO2022131575A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023219071A1 (en) * | 2022-05-13 | 2023-11-16 | 出光興産株式会社 | Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20130055198A (en) * | 2011-11-18 | 2013-05-28 | 롬엔드하스전자재료코리아유한회사 | Novel compounds for organic electronic material and organic electroluminescent device using the same |
KR101814875B1 (en) * | 2014-10-07 | 2018-01-05 | 주식회사 엘지화학 | Hetero-cyclic compound and organic electronic device using the same |
KR102040226B1 (en) * | 2016-12-14 | 2019-11-27 | 주식회사 엘지화학 | Organic light emitting device |
KR102038031B1 (en) * | 2017-09-15 | 2019-10-30 | 엘티소재주식회사 | Heterocyclic compound and organic light emitting device comprising the same |
CN108129429B (en) * | 2017-12-14 | 2021-07-20 | 张家港九力新材料科技有限公司 | Naphthalene benzofuran derivative and preparation method thereof |
-
2020
- 2020-12-14 KR KR1020200174143A patent/KR20220084559A/en unknown
-
2021
- 2021-11-16 WO PCT/KR2021/016686 patent/WO2022131575A1/en active Application Filing
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023219071A1 (en) * | 2022-05-13 | 2023-11-16 | 出光興産株式会社 | Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device |
Also Published As
Publication number | Publication date |
---|---|
WO2022131575A1 (en) | 2022-06-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR20230146997A (en) | Organic compound and electroluminescent device comprising the same | |
KR102356004B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
KR20220084559A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
KR20220116604A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
KR20220136613A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
KR20220139474A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
KR20230174766A (en) | Organic compound and electroluminescent device comprising the same | |
KR20220137294A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
KR20230013358A (en) | Organic compound and electroluminescent device comprising the same | |
KR20230031455A (en) | Organic compound and electroluminescent device comprising the same | |
KR20220100224A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
KR20220157681A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
KR20220140174A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
KR20220094826A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
KR20220167416A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
KR20240055330A (en) | Organic compound and electroluminescent device comprising the same | |
KR20220101829A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
KR20230120146A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
KR20220010440A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
KR20220142989A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
KR20220081550A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
KR20220164950A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
KR20220078216A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
KR20230076939A (en) | A plurality of host materials and organic electroluminescent device comprising the sam | |
KR20220098887A (en) | An electroluminescent compound and an electroluminescent device comprising the same |