KR20230174709A - Organic compound and electroluminescent device comprising the same - Google Patents
Organic compound and electroluminescent device comprising the same Download PDFInfo
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- KR20230174709A KR20230174709A KR1020230073386A KR20230073386A KR20230174709A KR 20230174709 A KR20230174709 A KR 20230174709A KR 1020230073386 A KR1020230073386 A KR 1020230073386A KR 20230073386 A KR20230073386 A KR 20230073386A KR 20230174709 A KR20230174709 A KR 20230174709A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 27
- 239000010410 layer Substances 0.000 claims abstract description 94
- 239000000463 material Substances 0.000 claims abstract description 31
- 239000012044 organic layer Substances 0.000 claims abstract description 27
- 239000000126 substance Substances 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims description 61
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 238000002347 injection Methods 0.000 claims description 21
- 239000007924 injection Substances 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 19
- 230000000903 blocking effect Effects 0.000 claims description 19
- 229910052805 deuterium Inorganic materials 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003367 polycyclic group Chemical group 0.000 claims description 12
- 230000005525 hole transport Effects 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 229940125904 compound 1 Drugs 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 230000015572 biosynthetic process Effects 0.000 description 40
- 238000003786 synthesis reaction Methods 0.000 description 40
- -1 1-methylpentyl group Chemical group 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 238000004519 manufacturing process Methods 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000002019 doping agent Substances 0.000 description 10
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 9
- 125000002950 monocyclic group Chemical group 0.000 description 9
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- 125000005264 aryl amine group Chemical group 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 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
- QIXPSFYLBFVSII-UHFFFAOYSA-N (9-phenylcarbazol-4-yl)boronic acid Chemical compound C12=CC=CC=C2C=2C(B(O)O)=CC=CC=2N1C1=CC=CC=C1 QIXPSFYLBFVSII-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 4
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 4
- PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 description 4
- GDUANFXPOZTYKS-UHFFFAOYSA-N 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid Chemical compound FC1=CC(OC)=CC(F)=C1C(=O)NC1=CC(Br)=CC2=C1OC(C(O)=O)=CC2=O GDUANFXPOZTYKS-UHFFFAOYSA-N 0.000 description 4
- PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 229940126179 compound 72 Drugs 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- MPSDYLBAJCSIMR-UHFFFAOYSA-N 4-bromo-6-phenyldibenzofuran Chemical compound BrC1=CC=CC(C2=CC=C3)=C1OC2=C3C1=CC=CC=C1 MPSDYLBAJCSIMR-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
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 150000001412 amines Chemical group 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 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 3
- 238000000605 extraction Methods 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 238000000034 method Methods 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- DMDPAJOXRYGXCB-UHFFFAOYSA-N (9,9-dimethylfluoren-2-yl)boronic acid Chemical compound C1=C(B(O)O)C=C2C(C)(C)C3=CC=CC=C3C2=C1 DMDPAJOXRYGXCB-UHFFFAOYSA-N 0.000 description 2
- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 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
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 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
- 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
- 125000003282 alkyl amino group 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
- 229940125773 compound 10 Drugs 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 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 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000011368 organic material Substances 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
- 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
- 150000003852 triazoles Chemical group 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 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 1
- RRCMGJCFMJBHQC-UHFFFAOYSA-N (2-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1Cl RRCMGJCFMJBHQC-UHFFFAOYSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 1
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 1
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- 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
- KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-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
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 description 1
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-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
- LGGSHXHPRHARFY-UHFFFAOYSA-N 4-bromo-6-phenyldibenzothiophene Chemical compound BrC1=CC=CC(C2=CC=C3)=C1SC2=C3C1=CC=CC=C1 LGGSHXHPRHARFY-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 1
- XQNMSKCVXVXEJT-UHFFFAOYSA-N 7,14,25,32-tetrazaundecacyclo[21.13.2.22,5.03,19.04,16.06,14.08,13.020,37.024,32.026,31.034,38]tetraconta-1(36),2,4,6,8,10,12,16,18,20(37),21,23(38),24,26,28,30,34,39-octadecaene-15,33-dione 7,14,25,32-tetrazaundecacyclo[21.13.2.22,5.03,19.04,16.06,14.08,13.020,37.025,33.026,31.034,38]tetraconta-1(37),2,4,6,8,10,12,16,18,20,22,26,28,30,32,34(38),35,39-octadecaene-15,24-dione Chemical compound O=c1c2ccc3c4ccc5c6nc7ccccc7n6c(=O)c6ccc(c7ccc(c8nc9ccccc9n18)c2c37)c4c56.O=c1c2ccc3c4ccc5c6c(ccc(c7ccc(c8nc9ccccc9n18)c2c37)c46)c1nc2ccccc2n1c5=O XQNMSKCVXVXEJT-UHFFFAOYSA-N 0.000 description 1
- NJIAKNWTIVDSDA-FQEVSTJZSA-N 7-[4-(1-methylsulfonylpiperidin-4-yl)phenyl]-n-[[(2s)-morpholin-2-yl]methyl]pyrido[3,4-b]pyrazin-5-amine Chemical compound C1CN(S(=O)(=O)C)CCC1C1=CC=C(C=2N=C(NC[C@H]3OCCNC3)C3=NC=CN=C3C=2)C=C1 NJIAKNWTIVDSDA-FQEVSTJZSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- IVLPUVAQMTXCFW-UHFFFAOYSA-N 9-(1-carbazol-9-yl-4-phenylcyclohexa-2,4-dien-1-yl)carbazole Chemical group C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)(N2C3=CC=CC=C3C3=CC=CC=C32)CC=C1C1=CC=CC=C1 IVLPUVAQMTXCFW-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
- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229940127007 Compound 39 Drugs 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
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- LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 1
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- 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
- QHZHWFKZIRMHRT-UHFFFAOYSA-N [4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 QHZHWFKZIRMHRT-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
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical group C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 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 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
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 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
- 229910052799 carbon Inorganic materials 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
- 229940126540 compound 41 Drugs 0.000 description 1
- 229940125844 compound 46 Drugs 0.000 description 1
- 229940126545 compound 53 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 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
- 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
- 238000003618 dip coating Methods 0.000 description 1
- DFBKLUNHFCTMDC-GKRDHZSOSA-N endrin Chemical compound C([C@@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@@H]2[C@H]2[C@@H]1O2 DFBKLUNHFCTMDC-GKRDHZSOSA-N 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
- 238000002474 experimental method Methods 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
- 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
- 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
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[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
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- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 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
- 238000002156 mixing Methods 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
- 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
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 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
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 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
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- FDBYIYFVSAHJLY-UHFFFAOYSA-N resmetirom Chemical compound N1C(=O)C(C(C)C)=CC(OC=2C(=CC(=CC=2Cl)N2C(NC(=O)C(C#N)=N2)=O)Cl)=N1 FDBYIYFVSAHJLY-UHFFFAOYSA-N 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
- 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
- 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C—CHEMISTRY; METALLURGY
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Abstract
본 발명은 유기발광소자 내의 발광층 등의 유기층 재료로 채용되어 발광 효율 및 양자 효율 등의 우수한 발광 특성을 구현할 수 있는 하기 [화학식 Ⅰ]로 표시되는 유기 화합물 및 이를 포함하는 유기발광소자를 제공하고자 한다.
[화학식 Ⅰ]
The present invention seeks to provide an organic compound represented by the following [Chemical Formula I], which can be used as an organic layer material such as a light-emitting layer in an organic light-emitting device to realize excellent light-emitting properties such as luminous efficiency and quantum efficiency, and an organic light-emitting device containing the same. .
[Formula Ⅰ]
Description
본 발명은 유기 화합물에 관한 것으로서, 더욱 상세하게는 화합물이 갖는 구조적 특징에 의해서 유기발광소자 내의 발광층 등의 유기층 재료로 채용되는 유기 화합물 및 이를 채용하여 발광 효율, 양자 효율 등의 발광 특성이 현저히 향상된 유기발광소자에 관한 것이다.The present invention relates to organic compounds, and more specifically, organic compounds used as organic layer materials such as light-emitting layers in organic light-emitting devices due to the structural characteristics of the compounds, and the use of these compounds to significantly improve luminous properties such as luminous efficiency and quantum efficiency. It is about organic light emitting devices.
유기발광소자는 투명 기판 위에도 소자를 형성할 수 있을 뿐 아니라, 플라즈마 디스플레이 패널 (Plasma Display Panel)이나 무기전계발광 (EL) 디스플레이에 비해 10 V 이하의 저전압 구동이 가능하고, 전력 소모가 비교적 적으며, 색감이 뛰어나다는 장점이 있고, 녹색, 청색, 적색의 3가지 색을 나타낼 수가 있어 최근에 차세대 디스플레이 소자로 많은 관심의 대상이 되고 있다.Organic light emitting devices not only can be formed on transparent substrates, but also can be driven at low voltages of 10 V or less compared to plasma display panels or inorganic electroluminescence (EL) displays, and consume relatively little power. , It has the advantage of excellent color and can display three colors of green, blue, and red, so it has recently been the subject of much attention as a next-generation display device.
다만, 이러한 유기발광소자가 상기와 같은 특징으로 발휘하기 위해서는 소자 내 유기층을 이루는 물질인 정공주입층, 정공수송층, 정공저지층, 발광층 호스트 및 도판트, 전자저지층, 전자수송층, 전자주입층 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 materials that make up the organic layers in the device, such as a hole injection layer, hole transport layer, hole blocking layer, light emitting layer host and dopant, electron blocking layer, electron transport layer, electron injection layer, etc. This should be supported by stable and efficient materials, but the development of stable and efficient organic layer materials for organic light-emitting devices 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 implement more stable organic light-emitting devices and achieve higher efficiency, longer lifespan, and enlargement of devices, additional improvements in terms of efficiency and lifespan characteristics are required. In particular, development of materials forming each organic layer of organic light-emitting devices is required. It is desperately needed.
특히, 발광층에서 최대의 효율을 얻기 위해서는 홀과 전자가 각각 안정적인 전기화학적 경로를 통하여 도판트로 이동하여 엑시톤을 형성할 수 있도록 호스트와 도판트의 에너지 밴드갭이 적절한 조합을 이루어야 한다.In particular, in order to obtain maximum efficiency in the light emitting layer, the energy band gap of the host and the dopant must be appropriately combined so that holes and electrons can each move to the dopant through a stable electrochemical path to form excitons.
따라서, 본 발명은 유기발광소자 내의 발광층 내의 호스트 재료로 채용되어 발광 효율 및 양자 효율 등의 우수한 발광 특성을 구현할 수 있는 유기 화합물 및 이를 포함하는 유기발광소자를 제공하고자 한다.Therefore, the present invention seeks to provide an organic compound that can be used as a host material in the light-emitting layer of an organic light-emitting device to realize excellent light-emitting properties such as luminous efficiency and quantum efficiency, and an organic light-emitting device containing the same.
본 발명은 상기 과제를 해결하기 위하여, 하기 [화학식 Ⅰ]로 표시되는 화합물 중에서 선택된 어느 하나의 유기 화합물 및 이를 발광층에 포함하는 유기발광소자를 제공한다.In order to solve the above problems, the present invention provides an organic compound selected from compounds represented by the following [Chemical Formula I] and an organic light-emitting device including the same in a light-emitting layer.
[화학식 Ⅰ][Formula Ⅰ]
상기 [화학식 Ⅰ]의 특징적인 구조 및 이에 의하여 구현되는 구체적인 화합물과 X, L, m, Ar1 내지 Ar3, D (중수소) 및 n의 정의에 대해서는 후술하기로 한다.The characteristic structure of the above [Chemical Formula I], specific compounds implemented thereby, and the definitions of X, L , m, Ar 1 to Ar 3 , D (deuterium), and n will be described later.
본 발명에 따른 유기 화합물은 유기발광소자 내의 발광층 호스트 재료로 사용되어 소자의 발광 효율 및 양자 효율 등의 우수한 발광 특성을 구현할 수 있어 조명 소자는 물론이고, 평판, 플렉시블, 웨어러블 디스플레이 등 다양한 디스플레이 소자에 유용하게 활용할 수 있다.The organic compound according to the present invention can be used as a host material for the light-emitting layer in an organic light-emitting device to realize excellent light-emitting properties such as luminous efficiency and quantum efficiency of the device, and can be used in various display devices such as lighting devices, flat panels, flexible displays, and wearable displays. It can be useful.
이하, 본 발명을 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명은 하기 [화학식 Ⅰ]로 표시되는 유기 화합물에 관한 것으로서, 구조적 특징에 의해서 유기발광소자 내의 발광층 호스트로 채용되어 발광효율 및 양자효율 등의 우수한 소자 특성을 갖는 유기발광소자를 구현할 수 있다.The present invention relates to an organic compound represented by the following [Chemical Formula I], which can be employed as a light-emitting layer host in an organic light-emitting device due to its structural characteristics to implement an organic light-emitting device having excellent device characteristics such as luminous efficiency and quantum efficiency.
[화학식 Ⅰ][Formula Ⅰ]
상기 [화학식 Ⅰ]에서,In the above [Chemical Formula I],
X는 O, S, 또는 CR1R2이다.X is O, S, or CR 1 R 2 .
상기 R1 및 R2는 수소, 시아노기, 할로겐기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 3 내지 30의 헤테로아릴기 중에서 선택된다.R 1 and R 2 are hydrogen, a cyano group, a halogen group, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, and a substituted or unsubstituted hetero group with 3 to 30 carbon atoms. It is selected from aryl groups.
또한, 상기 R1과 R2는 서로 연결되어 지환족 또는 방향족의 단일환 또는 다환 고리를 형성할 수 있다.Additionally, R 1 and R 2 may be connected to each other to form an alicyclic or aromatic monocyclic or polycyclic ring.
Ar1 및 Ar2는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기 중에서 선택되고, 이때 상기 Ar1 과 Ar2가 모두 수소인 경우는 제외한다.Ar 1 and Ar 2 are the same or different from each other, and are each independently selected from hydrogen, 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, wherein Ar Excluding cases where both 1 and Ar 2 are hydrogen.
Ar3은 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기 중에서 선택된다.Ar 3 is 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.
L은 직접 결합이거나, 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기이고, m은 0 내지 3의 정수이며, 상기 m이 2 이상인 경우 복수 개의 L은 서로 동일하거나 상이하다.L is a direct bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and m is an integer of 0 to 3. When m is 2 or more, the plurality of L's are the same or different from each other.
D는 중수소이고, n은 상기 [화학식 Ⅰ] 내의 수소가 중수소 (D)로 대체된 개수를 의미하고, n은 0 내지 60의 정수이다.D is deuterium, n means the number of hydrogens in [Chemical Formula I] replaced with deuterium (D), and n is an integer from 0 to 60.
상기 [화학식 Ⅰ]은 골격 구조는 물론, 이에 도입되는 R1 및 R2가 중수소일 수 있고, 또한, R1, R2, L 및 Ar1 내지 Ar3가 각각 부분적으로 중수소 (D)로 치환된 화합물, 즉 R1, R2, L 및 Ar1 내지 Ar3가 각각 적어도 하나 이상의 중수소를 치환기로 포함할 수 있다.In the [Formula I], not only the skeletal structure, but also R 1 and R 2 introduced therein may be deuterium, and R 1 , R 2 , L and Ar 1 to Ar 3 are each partially substituted with deuterium (D). The compounds, that is, R 1 , R 2 , L and Ar 1 to Ar 3 may each include at least one deuterium as a substituent.
이에 따라 본 발명의 일 실시예에 의하면, 본 발명에 따른 [화학식 Ⅰ]에서 상기 중수소 (D) 치환율이 10 ~ 90%일 수 있다.Accordingly, according to one embodiment of the present invention, the deuterium (D) substitution rate in [Chemical Formula I] according to the present invention may be 10 to 90%.
이와 같이 본 발명에 따른 화합물은 [화학식 Ⅰ] 구조 내의 일부 수소를 중수소로 대체함으로써, 종래 모이어티 구조에 따라 확인되는 유기발광소자의 낮은 수명 단점을 보완하여 보다 장수명을 갖는 유기발광소자를 구현 가능케 한다.In this way, the compound according to the present invention replaces some of the hydrogen in the structure of [Formula I] with deuterium, making it possible to implement an organic light-emitting device with a longer lifespan by compensating for the shortcomings of the low lifespan of organic light-emitting devices found according to the conventional moiety structure. do.
한편, 상기 R1, R2, L 및 Ar1 내지 Ar3의 정의에서, '치환 또는 비치환된'이라 함은 상기 R1, R2, L 및 Ar1 내지 Ar3이 각각 중수소, 할로겐기, 시아노기, 니트로기, 히드록시기, 알킬기, 시클로알킬기, 헤테로시클로알킬기, 알콕시기, 아릴기, 헤테로아릴기, 아민기 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 것을 의미한다.Meanwhile, the R 1 , R 2 , L And in the definition of Ar 1 to Ar 3 , ‘substituted or unsubstituted’ refers to R 1 , R 2 , L And Ar 1 to Ar 3 are each selected from the group consisting of deuterium, halogen group, cyano group, nitro group, hydroxy group, alkyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, aryl group, heteroaryl group, amine group and silyl group. Alternatively, it means being substituted with two or more substituents, being substituted with a substituent where two or more of the substituents are linked, or not having any substituents.
구체적인 예를 들면, 치환된 아릴기라 함은, 페닐기, 비페닐기, 나프탈렌기, 플루오레닐기, 파이레닐기, 페난트레닐기, 페릴렌기, 테트라세닐기, 안트라센닐기 등이 중수소 등의 다른 치환기로 치환된 것을 의미하고, 치환된 헤테로아릴기라 함은, 피리딜기, 티오페닐기, 트리아진기, 퀴놀린기, 페난트롤린기, 이미다졸기, 티아졸기, 옥사졸기, 카바졸기 및 이들의 축합헤테로고리기, 예컨대 벤즈퀴놀린기, 벤즈이미다졸기, 벤즈옥사졸기, 벤즈티아졸기, 벤즈카바졸기, 디벤조티오페닐기, 디벤조퓨란기 등이 역시 중수소 등의 다른 치환기로 치환된 것을 의미한다.For specific examples, a substituted aryl group refers to a phenyl group, biphenyl group, naphthalene group, fluorenyl group, pyrenyl group, phenanthrenyl group, perylene group, tetracenyl group, anthracenyl group, etc. substituted with another substituent such as deuterium. means, and substituted heteroaryl group refers to pyridyl group, thiophenyl group, triazine group, quinoline group, phenanthroline group, imidazole group, thiazole group, oxazole group, carbazole group and condensed heterocyclic groups thereof, such as This means that benzquinoline group, benzimidazole group, benzoxazole group, benzthiazole group, benzcarbazole group, dibenzothiophenyl group, dibenzofuran group, etc. are also substituted with other substituents such as deuterium.
본 발명에 있어서, 상기 치환기들의 예시들에 대해서 아래에서 구체적으로 설명하나, 이에 한정되는 것은 아니다.In the present invention, examples of the above substituents will be described in detail below, but are 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 straight chain 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, etc., but is not limited to these.
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 chain. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 20, which is within 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 , benzyloxy group, p-methylbenzyloxy group, etc., but is not limited thereto.
본 발명에 있어서, 상기 알킬기 내지 알콕시기는 중수소화된 알킬기 또는 알콕시기, 할로겐화된 알킬기 또는 알콕시기일 수 있으며, 이는 상기 알킬기 또는 알콕시기가 중수소 또는 할로겐기로 치환된 알킬기 또는 알콕시기를 의미한다.In the present invention, the alkyl group or alkoxy group may be a deuterated alkyl group or alkoxy group, a halogenated alkyl group, or an alkoxy group, which means an alkyl group or alkoxy group in which the alkyl group or alkoxy group is substituted with a deuterium or halogen group.
본 발명에 있어서, 아릴기는 단환식 또는 다환식일 수 있고, 탄소수는 특별히 한정되지 않으나 6 내지 30인 것이 바람직하며, 또한 시클로알킬 등이 융합된 다환식 아릴기 구조를 포함하고, 단환식 아릴기의 예로는 페닐기 (Ph), 비페닐기, 터페닐기, 스틸벤기 등이 있고, 다환식 아릴기의 예로는 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 테트라세닐기, 크라이세닐기, 플루오레닐기, 아세나프타센닐기, 트리페닐렌기, 플루오안트렌기 (fluoranthrene) 등이 있으나, 본 발명의 범위가 이들 예로만 한정되는 것은 아니다.In the present invention, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 30. It also includes a polycyclic aryl group structure fused with cycloalkyl, etc., and the monocyclic aryl group Examples of phenyl group (Ph), biphenyl group, terphenyl group, stilbene group, etc. Examples of polycyclic aryl groups include naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, 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 the structure of an open fluorenyl group, where the open fluorenyl group is a structure in which one ring compound is disconnected in a structure where 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.Additionally, the carbon atom of the ring may be substituted with one or more heteroatoms selected from N, S, and O, for example , , , etc.
또한, 본 발명에 있어서, 플루오레닐기는 상기 연결된 구조, 열린구조에 단환 또는 다환의 방향족 고리와 단환 또는 다환의 지환족 고리 등이 더 축합된 구조일 수 있다.Additionally, in the present invention, the fluorenyl group may have a structure in which a monocyclic or polycyclic aromatic ring and a monocyclic or polycyclic alicyclic ring, etc. are further condensed to the above linked structure or open structure.
본 발명에 있어서, 헤테로아릴기는 이종원자로 O, N 또는 S를 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 30인 것이 바람직하며, 시클로알킬 또는 헤테로시클로알킬 등이 융합된 다환식 헤테로아릴기 구조를 포함하며, 본 발명에서 이의 구체적인 예를 들면, 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 트리아졸기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 디벤조퓨라닐기, 페난트롤린기, 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기, 페녹사진기, 페노티아진기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present invention, the heteroaryl group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and is a polycyclic group fused with cycloalkyl or heterocycloalkyl, etc. It contains a heteroaryl group structure, and specific examples thereof in the present invention include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, and bipyridyl group. , pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, Dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, phenoxazine group, phenothiazine group, etc., but only these It is not limited.
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. Specific examples of such silyl groups include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, and dimethoxysilyl. Examples include phenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, etc., but are not limited thereto.
본 발명에서 사용되는 할로겐기의 구체적인 예로는 플루오르(F), 클로린(Cl), 브롬(Br) 등을 들 수 있다.Specific examples of the halogen group used in the present invention include fluorine (F), chlorine (Cl), and bromine (Br).
본 발명에 있어서, 시클로알킬기는 단환, 다환 및 스피로 알킬 라디칼을 지칭하고, 이를 포함하며, 바람직하게는 탄소수 3 내지 20의 고리 탄소 원자를 함유하는 것으로서, 시클로프로필, 시클로펜틸, 시클로헥실, 비시클로헵틸, 스피로데실, 스피로운데실, 아다만틸 등을 포함하며, 시클로알킬기는 임의로 치환될 수 있다.In the present invention, cycloalkyl groups refer to and include monocyclic, polycyclic and spiro alkyl radicals, and preferably contain ring carbon atoms having 3 to 20 carbon atoms, such as cyclopropyl, cyclopentyl, cyclohexyl, and bicyclo. It includes heptyl, spirodecyl, spiroundecyl, adamantyl, etc., and the cycloalkyl group may be optionally substituted.
본 발명에 있어서, 헤테로시클로알킬기는 하나 이상의 헤테로 원자를 함유하는 방향족 및 비방향족 시클릭 라디칼을 지칭하고, 이를 포함하며, 하나 이상의 헤테로원자는 O, S, N, P, B, Si 및 Se, 바람직하게는 O, N 또는 S로부터 선택되며, 구체적으로 N을 포함하는 경우 아지리딘, 피롤리딘, 피페리딘, 아제판, 아조칸 등일 수 있다.In the present invention, heterocycloalkyl groups refer to and include aromatic and non-aromatic cyclic radicals containing one or more heteroatoms, wherein one or more heteroatoms are O, S, N, P, B, Si and Se, It is preferably selected from O, N or S, and specifically, when it contains N, it may be aziridine, pyrrolidine, piperidine, azepane, azocan, etc.
본 발명에 있어서, 아민기는 -NH2, 알킬아민기, 아릴아민기, 아릴헤테로아릴아민기 등일 수 있고, 아릴아민기는 아릴로 치환된 아민을 의미하고, 알킬아민기는 알킬로 치환된 아민을 의미하는 것이며, 아릴헤테로아릴아민기는 아릴 및 헤테로아릴기로 치환된 아민을 의미하는 것으로서, 아릴아민기의 예로는 치환 또는 비치환된 모노아릴아민기, 치환 또는 비치환된 디아릴아민기, 또는 치환 또는 비치환된 트리아릴아민기가 있고, 상기 아릴아민기 및 아릴헤테로아릴아민기 중의 아릴기 및 헤테로아릴기는 단환식 아릴기, 단환식 헤테로아릴기일 수 있고, 다환식 아릴기, 다환식 헤테로아릴기일 수 있으며, 상기 아릴기, 헤테로아릴기를 2 이상을 포함하는 아릴아민기, 아릴헤테로아릴아민기는 단환식 아릴기(헤테로아릴기), 다환식 아릴기(헤테로아릴기), 또는 단환식 아릴기(헤테로아릴기)와 다환식 아릴기(헤테로아릴기)를 동시에 포함할 수 있다. 또한, 상기 아릴아민기 및 아릴헤테로아릴아민기 중의 아릴기, 헤테로아릴기는 전술한 아릴기, 헤테로아릴기의 예시 중에서 선택될 수 있다.In the present invention, the amine group may be -NH 2 , an alkylamine group, an arylamine group, an arylheteroarylamine group, etc., an arylamine group refers to an amine substituted with aryl, and an alkylamine group refers to an amine substituted with alkyl. The arylheteroarylamine group refers to an amine substituted with aryl and heteroaryl groups. Examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or There is an unsubstituted triarylamine group, and the aryl group and heteroaryl group in the arylamine group and arylheteroarylamine group may be a monocyclic aryl group, a monocyclic heteroaryl group, or a polycyclic aryl group or a polycyclic heteroaryl group. and the aryl group, the arylamine group containing two or more heteroaryl groups, and the arylheteroarylamine group include a monocyclic aryl group (heteroaryl group), a polycyclic aryl group (heteroaryl group), or a monocyclic aryl group (heteroaryl group). It may contain both an aryl group) and a polycyclic aryl group (heteroaryl group). In addition, the aryl group and heteroaryl group of the arylamine group and the arylheteroarylamine group may be selected from examples of the above-mentioned aryl group and heteroaryl group.
상기 [화학식 Ⅰ]로 표시되는 본 발명에 따른 유기 화합물은 그 구조적 특이성으로 인하여 유기발광소자의 유기층으로 사용될 수 있고, 보다 구체적으로는 유기층 내 발광층 호스트 등의 재료로 사용될 수 있다.The organic compound according to the present invention represented by the above [Formula I] can be used as an organic layer of an organic light-emitting device due to its structural specificity, and more specifically, can be used as a material such as a light-emitting layer host within the organic layer.
본 발명에 따른 [화학식 Ⅰ]로 표시되는 유기 화합물의 바람직한 구체예로는 하기 화합물들이 있으나, 이들에만 한정되는 것은 아니다.Preferred specific examples of the organic compound represented by [Chemical Formula I] according to the present invention include the following compounds, but are not limited to these.
상기와 같은 특징적 골격 구조 및 치환기를 통하여 골격 구조 및 치환기의 고유 특성을 갖는 유기 화합물을 합성할 수 있으며, 예컨대, 유기발광소자의 제조시 각 유기층에서 요구하는 조건들을 충족시키는 유기 화합물 물질을 제조할 수 있으며, 특히, 본 발명에 따른 [화학식 Ⅰ]의 화합물을 발광층 호스트로 채용한 경우 소자의 발광 효율 등의 소자 특성을 더욱 향상시킬 수 있다.Through the above-mentioned characteristic skeletal structure and substituents, organic compounds with unique characteristics of the skeletal structure and substituents can be synthesized. For example, when manufacturing an organic light-emitting device, an organic compound material that satisfies the conditions required for each organic layer can be manufactured. In particular, when the compound of [Chemical Formula I] according to the present invention is employed as a light-emitting layer host, device characteristics such as luminous efficiency of the device can be further improved.
또한, 본 발명은 제1 전극, 제2 전극 및 상기 제1 전극 및 제2 전극 사이에 개재되는 1층 이상의 유기층으로 이루어진 유기발광소자에 관한 것으로서, 상기 유기층에, 바람직하게는 호스트 및 도판트를 포함하는 발광층의 호스트로 상기에서 정의된 [화학식 Ⅰ]로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기발광소자에 관한 것이다.In addition, the present invention relates to an organic light-emitting device consisting of a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, and the organic layer preferably includes a host and a dopant. It relates to an organic light emitting device characterized in that it contains a compound represented by [Chemical Formula I] defined above as the host of the light emitting layer.
또한, 상기 발광층은 호스트와 도판트로 이루어지는 구조로서, 발광층은 도판트 재료를 더 포함할 수 있으며, 이때 도판트의 함량은 통상적으로 호스트 약 100 중량부를 기준으로 하여 약 0.01 내지 약 20 중량부의 범위에서 선택될 수 있으며, 이에 한정되는 것은 아니다.In addition, the light-emitting layer has a structure consisting of a host and a dopant, and the light-emitting layer may further include a dopant material. In this case, the content of the dopant is typically in the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host. It may be selected, but is not limited to this.
또한, 상기 발광층은 상기 본 발명에 따른 호스트 및 도판트 화합물 이외에도 다양한 호스트와 다양한 도판트 물질을 추가로 포함할 수 있으며, 이에 따라 상기 발광층 중 호스트는 물론이고, 도판트 재료 역시 서로 다른 화합물 1종 이상이 혼합 또는 적층되어 사용될 수 있다.In addition, the light-emitting layer may further include various hosts and various dopant materials in addition to the host and dopant compounds according to the present invention, and accordingly, not only the host but also the dopant material in the light-emitting layer may contain one type of different compound. The above may be mixed or laminated and used.
이에 따라 본 발명의 일 실시예에 의하면, 본 발명에 따른 유기발광소자는 발광층 내 호스트 재료를 복수 개로 구성할 수 있고, 이때 본 발명에 따른 [화학식 Ⅰ]로 표시되는 화합물 외에 다른 화합물을 1종 이상 더 포함하여 혼합 또는 적층하여 형성할 수 있다.Accordingly, according to one embodiment of the present invention, the organic light emitting device according to the present invention may consist of a plurality of host materials in the light emitting layer, and at this time, one type of compound other than the compound represented by [Chemical Formula I] according to the present invention It can be formed by mixing or stacking more than the above.
본 발명에 따른 유기 화합물을 이용하여 통상의 제조방법에 따라 유기발광소자에 적용할 수 있다.The organic compound according to the present invention can be applied to an organic light-emitting device according to a conventional manufacturing method.
본 발명의 일 실시예에 따른 유기발광소자는 제1 전극과 제2 전극 및 이 사이에 배치된 유기층을 포함하는 구조로 이루어질 수 있으며, 본 발명에 따른 유기 화합물을 소자의 유기층에 사용한다는 것을 제외하고는 통상의 소자의 제조 방법 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, a second electrode, and an organic layer disposed between them, except that the organic compound according to the present invention is used in the organic layer of the device. It can be manufactured using conventional device manufacturing methods and materials.
본 발명에 따른 유기발광소자의 유기층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층, 전자저지층 등을 포함하는 구조를 가질 수 있다. 그리고 필요에 따라 광효율 개선층 (Capping layer) 등을 포함하는 구조를 가질 수 있다. 그러나, 이에 한정되지 않고 더 적은 수, 더 많은 수의 유기층을 포함할 수도 있다.The organic layer of the organic light emitting device according to the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, etc. And, if necessary, it may have a structure that includes a light efficiency improvement layer (capping layer), etc. However, it is not limited to this and may include fewer or more 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 examples described later.
또한, 본 발명에 따른 유기발광소자는 스퍼터링 (sputtering)이나 전자빔 증발 (e-beam evaporation)과 같은 PVD (physical vapor deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공주입층, 정공수송층, 정공저지층, 발광층, 전자저지층, 전자수송층, 전자저지층 등을 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 deposits a metal, a conductive metal oxide, or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation. is deposited to form an anode, and an organic layer including a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron blocking layer, an electron transport layer, an electron blocking layer, etc. is formed thereon, and then an organic layer that can be used as a cathode is formed thereon. It can be manufactured by depositing the material.
이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기층, 양극 물질을 차례로 증착시켜 유기발광소자를 만들 수도 있다. 상기 유기층은 정공주입층, 정공수송층, 정공저지층, 발광층, 전자저지층, 전자수송층, 전자저지층 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 can also be made 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 hole blocking layer, a light emitting layer, an electron blocking layer, an electron transport layer, an electron blocking layer, etc., but is not limited to this and may have a single layer structure. In addition, the organic layer uses a variety of polymer materials and is formed using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, to form a smaller number of layers. It can be manufactured in layers.
양극은 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.The anode is usually preferably a material with a large work function to ensure smooth hole injection into the organic layer. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO). Metal oxides, combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT) , conductive polymers such as polypyrrole and polyaniline, but are not limited to these.
음극은 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 is generally preferably made of a material with a low work function to facilitate electron injection into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof, multilayers such as LiF/Al or LiO 2 /Al. Structural materials, etc., but are not limited to these.
정공주입층은 낮은 전압에서 양극으로부터 정공을 잘 주입받을 수 있는 물질로서, 정공주입 물질의 HOMO (highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기층의 HOMO 사이인 것이 바람직하다. 정공주입 물질의 구체적인 예로는 금속 포피린 (porphyrine), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴 헥사아자트리페닐렌, 퀴나크리돈 (quinacridone) 계열의 유기물, 페릴렌 (perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.The hole injection layer is a material that can easily receive holes from the anode at a low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) 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 hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene, quinacridone-based organic substances, perylene-based organic substances, Examples include anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited to these.
정공수송층은 양극이나 정공주입층으로부터 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, 이들에만 한정되는 것은 아니다.The hole transport layer is a material that can transport holes from the anode or hole injection layer and transfer them to the light emitting layer, and a material with high mobility for holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.
전자저지층은 전자의 이동을 저지하는 층으로, 정공수송층 위에 형성될 수 있으며, 전자저지층으로는 정공의 수송에는 영향을 미치지 않으면서 전자의 이동을 저지시킬 수 있는 것을 사용할 수 있다. 또한, 상기 전자저지층 상에는 발광층이 형성될 수 있고, 정공저지층, 전자수송층 및 전자주입층이 형성될 수 있다.The electron blocking layer is a layer that blocks the movement of electrons and can be formed on the hole transport layer. An electron blocking layer that can block the movement of electrons without affecting the transport of holes can be used. Additionally, a light-emitting layer may be formed on the electron blocking layer, and a hole blocking layer, an electron transport layer, and an electron injection layer may be formed.
정공저지층은 전자의 수송에는 영향을 미치지 않으면서 정공의 이동을 저지시킬 수 있는 것을 사용할 수 있으며, 이러한 정공저지층의 예로는 TPBi (1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl), BCP (2,9-dimethyl4,7-diphenyl-1,10-phenanthroline), CBP (4,4-bis(N-carbazolyl)-1,1'-biphenyl), PBD (2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole), PTCBI (bisbenzimidazo[2,1-a:1',2-b']anthra[2,1,9-def:6,5,10-d'e'f']diisoguinoline-10,21-dione) 또는 BPhen (4,7-diphenyl-1,10-phenanthroline) 등이 있으며, 이에 한정되는 것은 아니다.The hole blocking layer can be used to prevent the movement of holes without affecting the transport of electrons. An example of such a hole blocking layer is TPBi (1,3,5-tri(1-phenyl-1H-benzo). [d]imidazol-2-yl)phenyl), BCP (2,9-dimethyl4,7-diphenyl-1,10-phenanthroline), CBP (4,4-bis(N-carbazolyl)-1,1'-biphenyl ), PBD (2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole), PTCBI (bisbenzimidazo[2,1-a:1',2-b']anthra [2,1,9-def:6,5,10-d'e'f']diisoguinoline-10,21-dione) or BPhen (4,7-diphenyl-1,10-phenanthroline), etc. It is not limited.
발광층은 정공수송층과 전자수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물 (Alq3), 카르바졸 계열 화합물, 이량체화 스티릴 (dimerized styryl) 화합물, BAlq, 10-히드록시벤조 퀴놀린-금속 화합물, 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물, 폴리(p-페닐렌비닐렌) (PPV) 계열의 고분자, 스피로 (spiro) 화합물, 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.The light-emitting layer is a material that can emit light in the visible light range by transporting holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining them, and a material with 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 Examples include benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, and rubrene, but are not limited to these.
전자주입층은 음극으로부터 전달된 전자의 주입 효율이 높은 것을 사용할 수 있다. 이러한 전자 주입층의 예로는 리튬 퀴놀레이트(Liq) 등이 있으며, 이에 한정되는 것은 아니다.The electron injection layer can be one that has high injection efficiency of electrons transferred from the cathode. Examples of such electron injection layers include, but are not limited to, lithium quinolate (Liq).
전자수송층은 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.The electron transport layer is a material that can easily receive electrons from the cathode and transfer them to the light emitting layer, and a material with high electron mobility is suitable. Specific examples include, but are not limited to, an Al complex of 8-hydroxyquinoline, a complex containing 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 device according to the present invention may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
또한, 본 발명에 따른 유기발광 화합물은 유기 태양 전지, 유기 감광체, 유기 트랜지스터 등을 비롯한 유기전자소자에서도 유기발광소자에 적용되는 것과 유사한 원리로 작용할 수 있다.In addition, the organic light-emitting compound according to the present invention can function in organic electronic devices, including organic solar cells, organic photoreceptors, and organic transistors, on a principle similar to that applied to organic light-emitting devices.
이하, 본 발명의 이해를 돕기 위하여 바람직한 화합물의 합성예 및 소자 실시예를 제시한다. 그러나, 하기의 실시예는 본 발명을 예시하기 위한 것이며, 이에 의하여 본 발명의 범위가 한정되는 것은 아니다.Hereinafter, synthesis examples of preferred compounds and device examples are presented to aid understanding of the present invention. However, the following examples are for illustrating the present invention and are not intended to limit the scope of the present invention.
합성예Synthesis example 1 : 화합물 1의 합성 1: Synthesis of Compound 1
(1) (One) 제조예Manufacturing example 1 : 중간체 1-1의 합성 1: Synthesis of intermediate 1-1
4-Bromo-6-phenyldibenzofuran (10.0 g, 0.031 mol), B-(9-Phenyl-9H-carbazol-4-yl)boronic acid (10.7 g, 0.037 mol), K2CO3 (12.8 g, 0.093 mol), Pd(PPh3)4 (0.7 g, 0.0006 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 1-1>을 10.8 g (수율 71.9%) 수득하였다.4-Bromo-6-phenyldibenzofuran (10.0 g, 0.031 mol), B-(9-Phenyl-9H-carbazol-4-yl)boronic acid (10.7 g, 0.037 mol), K 2 CO 3 (12.8 g, 0.093 mol) ), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added to Pd(PPh 3 ) 4 (0.7 g, 0.0006 mol) and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 10.8 g (yield 71.9%) of <Intermediate 1-1>.
(2) (2) 제조예Manufacturing example 2 : 중간체 1-2의 합성 2: Synthesis of intermediate 1-2
중간체 1-1 (10.0 g, 0.021 mol) 을 CHCl3 100 mL에 용해시킨 후, Bromine (in CHCl3, 8.2 g, 0.052 mol)을 천천히 적가하여 상온에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 1-2>를 6.1 g (수율 52.5%) 수득하였다.Intermediate 1-1 (10.0 g, 0.021 mol) was dissolved in 100 mL of CHCl 3 , and then bromine (in CHCl 3 , 8.2 g, 0.052 mol) was slowly added dropwise and stirred at room temperature for 12 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 6.1 g of <Intermediate 1-2> (yield 52.5%).
(3) (3) 제조예Manufacturing example 3 : 화합물 1의 합성 3: Synthesis of Compound 1
중간체 1-2 (10.0 g, 0.018 mol), Phenyl Boronic acid (2.6 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 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 1>을 7.6 g (수율 76.4%) 수득하였다.Intermediate 1-2 (10.0 g, 0.018 mol), Phenyl Boronic acid (2.6 g, 0.021 mol), K 2 CO 3 (7.4 g, 0.053 mol), Pd(PPh 3 ) 4 (0.4 g, 0.0004 mol) toluene 200 mL, 50 mL of ethanol, and 50 mL of H 2 O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and recrystallized with a column to obtain 7.6 g of <Compound 1> (yield 76.4%).
LC/MS: m/z=561[(M)+]LC/MS: m/z=561[(M) + ]
합성예Synthesis example 2 : 화합물 10의 합성 2: Synthesis of Compound 10
(1) (One) 제조예Manufacturing example 1 : 화합물 10의 합성 1: Synthesis of Compound 10
중간체 1-2 (10.0 g, 0.018 mol), 9,9-dimethyl-2-fluoreneboronic acid (5.1 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 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 10>을 8.1 g (수율 67.5%) 수득하였다.Intermediate 1-2 (10.0 g, 0.018 mol), 9,9-dimethyl-2-fluoreneboronic acid (5.1 g, 0.021 mol), K 2 CO 3 (7.4 g, 0.053 mol), Pd(PPh 3 ) 4 (0.4 g, 0.0004 mol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, it was extracted, concentrated, and recrystallized with a column to obtain 8.1 g of <Compound 10> (yield 67.5%).
LC/MS: m/z=677[(M)+]LC/MS: m/z=677[(M) + ]
합성예Synthesis example 3 : 화합물 19의 합성 3: Synthesis of Compound 19
(1) (One) 제조예Manufacturing example 1 : 중간체 19-1의 합성 1: Synthesis of intermediate 19-1
중간체 1-2 (10.0 g, 0.018 mol), Bis(pinacolato)diboron (5.4 g, 0.021 mol), KOAc (5.2 g, 0.053 mol), Pd(dppf)Cl2 (0.8 g, 0.002 mol)에 dioxane 200 mL 넣고 100 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 19-1>을 7.6 g (수율 70.2%) 수득하였다.Intermediate 1-2 (10.0 g, 0.018 mol), Bis(pinacolato)diboron (5.4 g, 0.021 mol), KOAc (5.2 g, 0.053 mol), Pd(dppf)Cl 2 (0.8 g, 0.002 mol) dioxane 200 mL was added and stirred at 100°C for 12 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 7.6 g of <Intermediate 19-1> (yield 70.2%).
(2) (2) 제조예Manufacturing example 2 : 화합물 19의 합성 2: Synthesis of Compound 19
중간체 19-1 (10.0 g, 0.016 mol) 2-chloro-4-phenylquinazoline (4.7 g, 0.020 mol), K2CO3 (6.8 g, 0.049 mol), Pd(PPh3)4 (0.4 g, 0.0003 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 19>를 7.1 g (수율 62.9%) 수득하였다.Intermediate 19-1 (10.0 g, 0.016 mol) 2-chloro-4-phenylquinazoline (4.7 g, 0.020 mol), K 2 CO 3 (6.8 g, 0.049 mol), Pd(PPh 3 ) 4 (0.4 g, 0.0003 mol) ), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 7.1 g of <Compound 19> (yield 62.9%).
LC/MS: m/z=689[(M)+]LC/MS: m/z=689[(M) + ]
합성예Synthesis example 4 : 화합물 48의 합성 4: Synthesis of Compound 48
(1) (One) 제조예Manufacturing example 1 : 중간체 48-1의 합성 1: Synthesis of intermediate 48-1
4,6-dibromodibenzofuran (10.0 g, 0.031 mol), B-(9-Phenyl-9H-carbazol-4-yl)boronic acid (10.6 g, 0.037 mol), K2CO3 (12.7 g, 0.092 mol), Pd(PPh3)4 (0.7 g, 0.0006 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 48-1>을 6.8 g (수율 45.4%) 수득하였다.4,6-dibromodibenzofuran (10.0 g, 0.031 mol), B-(9-Phenyl-9H-carbazol-4-yl)boronic acid (10.6 g, 0.037 mol), K 2 CO 3 (12.7 g, 0.092 mol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added to Pd(PPh 3 ) 4 (0.7 g, 0.0006 mol) and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 6.8 g (yield 45.4%) of <Intermediate 48-1>.
(2) (2) 제조예Manufacturing example 2 : 중간체 48-2의 합성 2: Synthesis of intermediate 48-2
중간체 48-1 (10.0 g, 0.021 mol), 4-Biphenylboronic acid (4.9 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 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 48-2>를 8.4 g (수율 73.0%) 수득하였다.Intermediate 48-1 (10.0 g, 0.021 mol), 4-Biphenylboronic acid (4.9 g, 0.025 mol), K 2 CO 3 (8.5 g, 0.061 mol), Pd(PPh 3 ) 4 (0.5 g, 0.0004 mol) 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 8.4 g (yield 73.0%) of <Intermediate 48-2>.
(3) (3) 제조예Manufacturing example 3 : 중간체 48-3의 합성 3: Synthesis of intermediate 48-3
중간체 48-2 (10.0 g, 0.018 mol)를 CHCl3 100 mL에 용해시킨 후, Bromine (in CHCl3, 7.1 g, 0.045 mol)을 천천히 적가하여 상온에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 48-3>을 5.2 g (수율 45.6%) 수득하였다.Intermediate 48-2 (10.0 g, 0.018 mol) was dissolved in 100 mL of CHCl 3 , and then bromine (in CHCl 3 , 7.1 g, 0.045 mol) was slowly added dropwise and stirred at room temperature for 12 hours to react. After completion of the reaction, the extract was extracted, concentrated, and recrystallized using a column to obtain 5.2 g of <Intermediate 48-3> (yield 45.6%).
(4) (4) 제조예Manufacturing example 4 : 화합물 48의 합성 4: Synthesis of Compound 48
중간체 48-3 (10.0 g, 0.016 mol), Phenyl Boronic acid (2.3 g, 0.019 mol), K2CO3 (6.5 g, 0.047 mol), Pd(PPh3)4 (0.4 g, 0.0003 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 48>을 7.6 g (수율 76.3%) 수득하였다.Intermediate 48-3 (10.0 g, 0.016 mol), Phenyl Boronic acid (2.3 g, 0.019 mol), K 2 CO 3 (6.5 g, 0.047 mol), Pd(PPh 3 ) 4 (0.4 g, 0.0003 mol) toluene 200 mL, 50 mL of ethanol, and 50 mL of H 2 O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and recrystallized with a column to obtain 7.6 g of <Compound 48> (yield 76.3%).
LC/MS: m/z=637[(M)+]LC/MS: m/z=637[(M) + ]
합성예Synthesis example 5 : 화합물 72의 합성 5: Synthesis of Compound 72
(1) (One) 제조예Manufacturing example 1 : 중간체 72-1의 합성 1: Synthesis of intermediate 72-1
중간체 48-1 (10.0 g, 0.021 mol), (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (8.7 g, 0.025 mol), K2CO3 (8.5 g, 0.061 mol), Pd(PPh3)4 (0.5 g, 0.0006 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 72-1>을 8.1 g (수율 55.2%) 수득하였다.Intermediate 48-1 (10.0 g, 0.021 mol), (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (8.7 g, 0.025 mol), K 2 CO 3 (8.5 g, 0.061 mol) and Pd(PPh 3 ) 4 (0.5 g, 0.0006 mol) were added with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O, and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 8.1 g (yield 55.2%) of <Intermediate 72-1>.
(2) (2) 제조예Manufacturing example 2 : 중간체 72-2의 합성 2: Synthesis of intermediate 72-2
중간체 72-1 (10.0 g, 0.014 mol)를 CHCl3 100 mL에 용해시킨 후, Bromine (in CHCl3, 5.6 g, 0.035 mol)을 천천히 적가하여 상온에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 72-2>를 5.2 g (수율 46.8%) 수득하였다.Intermediate 72-1 (10.0 g, 0.014 mol) was dissolved in 100 mL of CHCl 3 , and then bromine (in CHCl 3 , 5.6 g, 0.035 mol) was slowly added dropwise and stirred at room temperature for 12 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 5.2 g of <Intermediate 72-2> (yield 46.8%).
(3) (3) 제조예Manufacturing example 3 : 화합물 72의 합성 3: Synthesis of Compound 72
중간체 72-2 (10.0 g, 0.013 mol), Phenyl Boronic acid (1.8 g, 0.015 mol), K2CO3 (5.2 g, 0.038 mol), Pd(PPh3)4 (0.3 g, 0.0003 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 72>를 7.6 g (수율 76.3%) 수득하였다.Intermediate 72-2 (10.0 g, 0.013 mol), Phenyl Boronic acid (1.8 g, 0.015 mol), K 2 CO 3 (5.2 g, 0.038 mol), Pd(PPh 3 ) 4 (0.3 g, 0.0003 mol) toluene 200 mL, 50 mL of ethanol, and 50 mL of H 2 O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and recrystallized with a column to obtain 7.6 g of <Compound 72> (yield 76.3%).
LC/MS: m/z=792[(M)+]LC/MS: m/z=792[(M) + ]
합성예Synthesis example 6 : 화합물 83의 합성 6: Synthesis of Compound 83
(1) (One) 제조예Manufacturing example 1 : 중간체 83-1의 합성 1: Synthesis of intermediate 83-1
4-Bromo-6-phenyldibenzofuran (10.0 g, 0.031 mol), 2-Chlorophenylboronic acid (5.8 g, 0.037 mol), K2CO3 (12.8 g, 0.093 mol), Pd(PPh3)4 (0.7 g, 0.6 mmol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 83-1>을 7.0 g (수율 63.8%) 수득하였다.4-Bromo-6-phenyldibenzofuran (10.0 g, 0.031 mol), 2-Chlorophenylboronic acid (5.8 g, 0.037 mol), K 2 CO 3 (12.8 g, 0.093 mol), Pd(PPh 3 ) 4 (0.7 g, 0.6 mmol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and recrystallized using a column to obtain 7.0 g of <Intermediate 83-1> (yield 63.8%).
(2) (2) 제조예Manufacturing example 2 : 화합물 83의 합성 2: Synthesis of Compound 83
중간체 83-1 (10.0 g, 0.028 mol), B-(9-Phenyl-9H-carbazol-4-yl)boronic acid (9.7 g, 0.034 mol), K2CO3 (11.7 g, 0.085 mol), Pd(OAc)2 (1.6 g, 0.001 mol), X-Phos (1.3 g, 0.003 mol), THF 200 mL와 H2O 50 mL를 넣고 70 ℃에서 6시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 83>을 11.4 g (수율 72.0%) 수득하였다.Intermediate 83-1 (10.0 g, 0.028 mol), B-(9-Phenyl-9H-carbazol-4-yl)boronic acid (9.7 g, 0.034 mol), K 2 CO 3 (11.7 g, 0.085 mol), Pd (OAc ) 2 (1.6 g, 0.001 mol), After completion of the reaction, the extract was extracted, concentrated, and recrystallized with a column to obtain 11.4 g of <Compound 83> (yield 72.0%).
LC/MS: m/z=561[(M)+]LC/MS: m/z=561[(M) + ]
합성예Synthesis example 7 : 화합물 128의 합성 7: Synthesis of Compound 128
(1) (One) 제조예Manufacturing example 1 : 중간체 128-1의 합성 1: Synthesis of intermediate 128-1
4-Bromo-6-phenyldibenzofuran (10.0 g, 0.031 mol), 4-Chlorophenylboronic acid (5.8 g, 0.037 mol), K2CO3 (12.8 g, 0.093 mol), Pd(PPh3)4 (0.7 g, 0.0006 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 128-1>을 7.2 g (수율 65.6%) 수득하였다.4-Bromo-6-phenyldibenzofuran (10.0 g, 0.031 mol), 4-Chlorophenylboronic acid (5.8 g, 0.037 mol), K 2 CO 3 (12.8 g, 0.093 mol), Pd(PPh 3 ) 4 (0.7 g, 0.0006 mol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, extraction was performed, concentration was performed, and then column was used to obtain 7.2 g of <Intermediate 128-1> (yield 65.6%).
(2) (2) 제조예Manufacturing example 2 : 중간체 128-2의 합성 2: Synthesis of intermediate 128-2
중간체 128-1 (10.0 g, 0.028 mol), B-(9-Phenyl-9H-carbazol-4-yl)boronic acid (9.7 g, 0.034 mol), K2CO3 (11.7 g, 0.085 mol), Pd(OAc)2 (1.6 g, 0.001 mol), X-Phos (1.3 g, 0.003 mol), THF 200 mL와 H2O 50 mL를 넣고 70 ℃에서 6시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 128-2>를 11.2 g (수율 70.8%) 수득하였다Intermediate 128-1 (10.0 g, 0.028 mol), B-(9-Phenyl-9H-carbazol-4-yl)boronic acid (9.7 g, 0.034 mol), K 2 CO 3 (11.7 g, 0.085 mol), Pd (OAc ) 2 (1.6 g, 0.001 mol), After completion of the reaction, extraction was performed, concentration was performed, and 11.2 g of <Intermediate 128-2> was obtained (yield 70.8%).
(3) (3) 제조예Manufacturing example 3 : 중간체 128-3의 합성 3: Synthesis of intermediate 128-3
중간체 128-2 (10.0 g, 0.018 mol)을 CHCl3 100 mL에 용해시킨 후, Bromine (in CHCl3, 7.1 g, 0.045 mol)을 천천히 적가하여 상온에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 128-3>을 4.8 g (수율 42.1%) 수득하였다.Intermediate 128-2 (10.0 g, 0.018 mol) was dissolved in 100 mL of CHCl 3 , and then bromine (in CHCl 3 , 7.1 g, 0.045 mol) was slowly added dropwise and stirred at room temperature for 12 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 4.8 g of <Intermediate 128-3> (yield 42.1%).
(4) (4) 제조예Manufacturing example 4 : 화합물 128의 합성 4: Synthesis of Compound 128
중간체 128-3 (10.0 g, 0.016 mol), 9,9-dimethyl-2-fluoreneboronic acid (4.5 g, 0.019 mol), K2CO3 (6.5 g, 0.047 mol), Pd(PPh3)4 (0.4 g, 0.3 mmol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 128>을 7.5 g (수율 59.5%) 수득하였다.Intermediate 128-3 (10.0 g, 0.016 mol), 9,9-dimethyl-2-fluoreneboronic acid (4.5 g, 0.019 mol), K 2 CO 3 (6.5 g, 0.047 mol), Pd(PPh 3 ) 4 (0.4 g, 0.3 mmol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and recrystallized with a column to obtain 7.5 g (59.5% yield) of <Compound 128>.
LC/MS: m/z=753[(M)+]LC/MS: m/z=753[(M) + ]
합성예Synthesis example 8 : 화합물 132의 합성 8: Synthesis of Compound 132
(1) (One) 제조예Manufacturing example 1 : 화합물 132의 합성 1: Synthesis of Compound 132
중간체 128-1 (10.0 g, 0.028 mol), B-(9-[1,1'-Biphenyl]-3-yl-9H-carbazol-4-yl)boronic acid (12.3 g, 0.034 mol), K2CO3 (11.7 g, 0.085 mol), Pd(OAc)2 (1.6 g, 0.001 mol), X-Phos (1.3 g, 0.003 mol), THF 200 mL와 H2O 50 mL를 넣고 70 ℃에서 6시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 132>를 11.2 g (수율 70.8%) 수득하였다Intermediate 128-1 (10.0 g, 0.028 mol), B-(9-[1,1'-Biphenyl]-3-yl-9H-carbazol-4-yl)boronic acid (12.3 g, 0.034 mol), K 2 Add CO 3 (11.7 g , 0.085 mol), Pd(OAc) 2 (1.6 g, 0.001 mol), The reaction was stirred for a while. After completion of the reaction, extraction and concentration were performed on a column and recrystallization to obtain 11.2 g of <Compound 132> (yield 70.8%).
LC/MS: m/z=637[(M)+]LC/MS: m/z=637[(M) + ]
합성예Synthesis example 9 : 화합물 140의 합성 9: Synthesis of Compound 140
(1) (One) 제조예Manufacturing example 1 : 중간체 140-1의 합성 1: Synthesis of intermediate 140-1
4-Bromo-6-phenyldibenzothiophene (10.0 g, 0.030 mol), B-(9-Phenyl-9H-carbazol-4-yl)boronic acid (10.2 g, 0.035 mol), K2CO3 (12.2 g, 0.088 mol), Pd(PPh3)4 (0.7 g, 0.0006 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 140-1>을 8.1 g (수율 54.8%) 수득하였다.4-Bromo-6-phenyldibenzothiophene (10.0 g, 0.030 mol), B-(9-Phenyl-9H-carbazol-4-yl)boronic acid (10.2 g, 0.035 mol), K 2 CO 3 (12.2 g, 0.088 mol) ), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added to Pd(PPh 3 ) 4 (0.7 g, 0.0006 mol) and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 8.1 g (yield 54.8%) of <Intermediate 140-1>.
(2) (2) 제조예Manufacturing example 2 : 중간체 140-2의 합성 2: Synthesis of intermediate 140-2
중간체 140-1 (10.0 g, 0.020 mol)을 CHCl3 100 mL에 용해시킨 후, Bromine (in CHCl3, 8.0 g, 0.050 mol)을 천천히 적가하여 상온에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 140-2>를 4.1 g (수율 35.4%) 수득하였다.Intermediate 140-1 (10.0 g, 0.020 mol) was dissolved in 100 mL of CHCl 3 , and bromine (in CHCl 3 , 8.0 g, 0.050 mol) was slowly added dropwise and stirred at room temperature for 12 hours to react. After completion of the reaction, it was extracted, concentrated, and then recrystallized with a column to obtain 4.1 g of <Intermediate 140-2> (yield 35.4%).
(3) (3) 제조예Manufacturing example 3 : 화합물 140의 합성 3: Synthesis of Compound 140
중간체 140-2 (10.0 g, 0.017 mol), Phenyl Boronic acid (2.5 g, 0.021 mol), K2CO3 (7.1 g, 0.052 mol), Pd(PPh3)4 (0.4 g, 0.0003 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 140>을 7.2 g (수율 72.4%) 수득하였다.Intermediate 140-2 (10.0 g, 0.017 mol), Phenyl Boronic acid (2.5 g, 0.021 mol), K 2 CO 3 (7.1 g, 0.052 mol), Pd(PPh 3 ) 4 (0.4 g, 0.0003 mol) toluene 200 mL, 50 mL of ethanol, and 50 mL of H 2 O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and recrystallized with a column to obtain 7.2 g of <Compound 140> (yield 72.4%).
LC/MS: m/z=577[(M)+]LC/MS: m/z=577[(M) + ]
소자 device 실시예Example
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 torr가 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 using an ITO glass substrate to which the ITO transparent electrode is attached on a glass substrate of 25 mm × 25 mm × 0.7 mm. and then washed. After the substrate was mounted in a vacuum chamber and the base pressure was set to 1 × 10 -6 torr, organic materials and metals were deposited on the ITO in the following structure.
소자 device 실시예Example 1 내지 45 1 to 45
본 발명에 따라 구현되는 화합물을 발광층 내 호스트로 사용하여 하기와 같은 소자 구조를 갖는 유기발광소자를 제작하여, 전류 효율을 포함한 발광 특성을 측정하였다. An organic light-emitting device having the following device structure was manufactured using the compound implemented according to the present invention as a host in the light-emitting layer, and light-emitting properties including current efficiency were measured .
ITO / 정공주입층 (HAT-CN, 5 nm) / 정공수송층 (HT1, 100 nm) / 전자저지층 (EB1, 10 nm) / 발광층 (제1 호스트:제2 호스트:Ir(ppy)3, 30 nm) / 전자수송층 (ET1, 30 nm) / LiF (1 nm) / Al (100 nm)ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (HT1, 100 nm) / electron blocking layer (EB1, 10 nm) / light emitting layer (1st host: 2nd host: Ir(ppy) 3 , 30 nm) / electron transport layer (ET1, 30 nm) / LiF (1 nm) / Al (100 nm)
ITO 투명 전극 상부에 정공주입층을 형성하기 위해 [HAT-CN]을 5 nm의 두께로 성막하고, 이후 정공수송층은 [HT1]을 사용하여 100 nm 성막하였다. 정공저지층은 [EB1]을 사용하여 10 nm의 두께로 증착하였다. 또한, 발광층은 복수의 호스트로 구성하면서, 제1 호스트는 하기 [표 1]에 기재된 본 발명에 따른 화합물을, 제2 호스트는 하기 [GH2]를 사용하여 6:4로 혼합하여 사용하였으며, 도판트는 Ir(ppy)3를 도핑하여 30 nm 두께로 공증착하였다. 추가로 전자수송층 (하기 [ET1] 화합물 Liq 50% 도핑) 30 nm 성막하였다. 전자주입층으로 LiF 1nm 두께로 증착하고 이어서 Al 100 nm를 성막하여 유기발광소자를 제작하였다.To form a hole injection layer on the top of the ITO transparent electrode, [HAT-CN] was deposited to a thickness of 5 nm, and then a hole transport layer was deposited at 100 nm using [HT1]. The hole blocking layer was deposited to a thickness of 10 nm using [EB1]. In addition, the light-emitting layer was composed of a plurality of hosts, and the first host was a compound according to the present invention shown in Table 1 below, and the second host was mixed in a ratio of 6:4 using [GH2] below. Ir(ppy) 3 was doped and co-deposited to a thickness of 30 nm. Additionally, a 30 nm electron transport layer (50% doped with [ET1] compound Liq below) was deposited. An organic light emitting device was manufactured by depositing LiF to a thickness of 1 nm as an electron injection layer and then forming a 100 nm layer of Al.
소자 device 비교예Comparative example 1 One
소자 비교예 1을 위한 유기발광소자는 상기 실시예 1의 소자구조에서 제1 호스트로 본 발명에 따른 화합물 대신 하기 [GH1]을 사용한 것을 제외하고 동일하게 제작하였다.The organic light emitting device for Comparative Device Example 1 was manufactured in the same manner as in the device structure of Example 1 except that [GH1] below was used as the first host instead of the compound according to the present invention.
실험예Experiment example 1: 소자 1: element 실시예Example 1 내지 45의 발광 특성 Luminous properties from 1 to 45
상기 실시예 및 비교예에 따라 제조된 유기발광소자에 대해서 Source meter (Model 237, Keithley)와 휘도계 (PR-650, Photo Research)를 이용하여 구동 전압, 전류 효율 및 색좌표를 측정하였고, 1,000 nit 기준의 결과값은 하기 [표 1]과 같다.The driving voltage, current efficiency, and color coordinates of the organic light emitting devices manufactured according to the above examples and comparative examples were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), and were measured at 1,000 nit. The standard result values are shown in [Table 1] below.
상기 [표 1]에 나타낸 결과를 살펴보면, 복수 개의 호스트 화합물로 구성되는 발광층을 채용한 유기발광소자에 있어서, 본 발명에 따른 화합물을 발광층 내 제1 호스트로 채용하면서 복수 개의 호스트로 구성한 경우에, 종래 호스트 화합물로서 본 발명에 따른 화합물이 갖는 구조적 특징과 대비되는 화합물을 이용하여 구성한 소자 (비교예 1)에 비하여 저전압 구동 특성 및 전류 효율 등의 발광 특성이 현저히 우수함을 확인할 수 있다.Looking at the results shown in [Table 1], in an organic light-emitting device employing a light-emitting layer composed of a plurality of host compounds, when the compound according to the present invention is employed as the first host in the light-emitting layer and is composed of a plurality of hosts, It can be confirmed that the luminous properties, such as low-voltage driving characteristics and current efficiency, are significantly superior to a device (Comparative Example 1) constructed using a compound that has structural characteristics and contrasts with the structural characteristics of the compound according to the present invention as a conventional host compound.
[HAT-CN] [HT1] [EB1] [ET1][HAT-CN] [HT1] [EB1] [ET1]
[GH1] [GH2] [Ir(ppy)3][GH1] [GH2] [Ir(ppy) 3 ]
Claims (11)
[화학식 Ⅰ]
상기 [화학식 Ⅰ]에서,
X는 O, S, 또는 CR1R2이고,
상기 R1 및 R2는 수소, 시아노기, 할로겐기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 3 내지 30의 헤테로아릴기 중에서 선택되는 어느 하나이며,
상기 R1과 R2는 서로 연결되어 지환족 또는 방향족의 단일환 또는 다환 고리를 형성할 수 있고,
Ar1 및 Ar2는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기 중에서 선택되는 어느 하나이고 (단, Ar1 과 Ar2가 모두 수소인 경우는 제외함),
Ar3은 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기 중에서 선택되는 어느 하나이며,
L은 직접 결합이거나, 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기이고, m은 0 내지 3의 정수이며, 상기 m이 2 이상인 경우 복수 개의 L은 서로 동일하거나 상이하며,
D는 중수소이고, n은 상기 [화학식 Ⅰ내의 수소가 중수소 (D)로 대체된 개수를 의미하고, n은 0 내지 60의 정수이다.Organic compounds represented by the following [Chemical Formula I]:
[Formula Ⅰ]
In the above [Chemical Formula I],
X is O, S, or CR 1 R 2 ,
R 1 and R 2 are hydrogen, a cyano group, a halogen group, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, and a substituted or unsubstituted hetero group with 3 to 30 carbon atoms. Any one selected from the aryl group,
R 1 and R 2 may be connected to each other to form an alicyclic or aromatic monocyclic or polycyclic ring,
Ar 1 and Ar 2 are the same as or different from each other, and are each independently selected from hydrogen, 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 ( However, excluding the case where Ar 1 and Ar 2 are both hydrogen),
Ar 3 is any one 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,
L is a direct bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, m is an integer of 0 to 3, and when m is 2 or more, the plurality of Ls are the same or different from each other,
D is deuterium, n refers to the number of hydrogens in the formula (I) replaced with deuterium (D), and n is an integer from 0 to 60.
상기 R1, R2, L 및 Ar1 내지 Ar3의 정의에서, '치환 또는 비치환된'이라 함은 상기 R1, R2, L 및 Ar1 내지 Ar3이 각각 중수소, 할로겐기, 시아노기, 니트로기, 히드록시기, 알킬기, 시클로알킬기, 헤테로시클로알킬기, 알콕시기, 아릴기, 헤테로아릴기, 아민기 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 것을 의미하는 유기 화합물.According to paragraph 1,
The R 1 , R 2 , L And in the definition of Ar 1 to Ar 3 , ‘substituted or unsubstituted’ refers to R 1 , R 2 , L And Ar 1 to Ar 3 are each selected from the group consisting of deuterium, halogen group, cyano group, nitro group, hydroxy group, alkyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, aryl group, heteroaryl group, amine group and silyl group. or an organic compound meaning that it is substituted with two or more substituents, is substituted with a substituent in which two or more of the substituents are linked, or does not have any substituents.
상기 [화학식 Ⅰ]은 [화학식 Ⅰ] 내에 존재하는 수소가 부분적으로 중수소 (D)로 치환된 화합물인 것을 특징으로 하고, 상기 중수소 (D) 치환율이 10 ~ 90%인 것을 특징으로 하는 유기 화합물.According to paragraph 1,
[Formula I] is an organic compound characterized in that the hydrogen present in [Formula I] is partially substituted with deuterium (D), and the deuterium (D) substitution rate is 10 to 90%.
상기 중수소 (D) 치환율이 20 ~ 80%인 것을 특징으로 하는 유기 화합물.According to paragraph 3,
An organic compound characterized in that the deuterium (D) substitution rate is 20 to 80%.
상기 중수소 (D) 치환율이 30 ~ 70%인 것을 특징으로 하는 유기 화합물.According to clause 4,
An organic compound characterized in that the deuterium (D) substitution rate is 30 to 70%.
상기 [화학식 Ⅰ]은 하기 [화합물 1] 내지 [화합물 331] 중에서 선택되는 것을 특징으로 하는 유기 화합물:
According to paragraph 1,
[Formula I] is an organic compound selected from the following [Compound 1] to [Compound 331]:
상기 유기층 중 1 층 이상은 제1항에 따른 [화학식 Ⅰ]의 유기 화합물을 포함하는 것인 유기발광소자.An organic light-emitting device comprising a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode,
An organic light emitting device wherein at least one of the organic layers includes an organic compound of [Chemical Formula I] according to claim 1.
상기 유기층은 전자주입층, 전자수송층, 정공주입층, 정공수송층, 전자저지층, 정공저지층 및 발광층 중 1층 이상을 포함하고,
상기 층들 중 1층 이상이 상기 [화학식 Ⅰ]로 표시되는 유기 화합물을 포함하는 것을 특징으로 하는 유기발광소자.In clause 7,
The organic layer includes one or more of an electron injection layer, an electron transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, and a light emitting layer,
An organic light-emitting device, wherein at least one of the layers includes an organic compound represented by the formula (I).
상기 발광층에 상기 [화학식 Ⅰ]로 표시되는 유기 화합물을 포함하는 것을 특징으로 하는 유기발광소자.According to clause 8,
An organic light-emitting device comprising an organic compound represented by [Chemical Formula I] in the light-emitting layer.
상기 [화학식 Ⅰ]로 표시되는 유기 화합물은 발광층 내 호스트 재료인 것을 특징으로 하는 유기발광소자.According to clause 9,
An organic light-emitting device, characterized in that the organic compound represented by [Chemical Formula I] is a host material in the light-emitting layer.
상기 호스트 재료는 상기 상기 [화학식 Ⅰ]로 표시되는 유기 화합물 외에 다른 화합물을 1종 이상 더 포함하여 복수 개로 혼합 또는 적층되어 구성되는 것을 특징으로 하는 유기발광소자.According to clause 10,
An organic light-emitting device, wherein the host material includes one or more other compounds in addition to the organic compound represented by [Chemical Formula I] and is mixed or stacked in plural pieces.
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| KR20140073695A (en) * | 2012-12-06 | 2014-06-17 | 롬엔드하스전자재료코리아유한회사 | Organic Electroluminescent Compounds and Organic Electroluminescent Device Comprising the Same |
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