JP6691211B2 - 有機光電子素子用組成物、有機光電子素子および表示装置 - Google Patents
有機光電子素子用組成物、有機光電子素子および表示装置 Download PDFInfo
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- JP6691211B2 JP6691211B2 JP2018521113A JP2018521113A JP6691211B2 JP 6691211 B2 JP6691211 B2 JP 6691211B2 JP 2018521113 A JP2018521113 A JP 2018521113A JP 2018521113 A JP2018521113 A JP 2018521113A JP 6691211 B2 JP6691211 B2 JP 6691211B2
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- 239000000203 mixture Substances 0.000 title claims description 62
- 230000005693 optoelectronics Effects 0.000 title claims description 40
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- 125000003118 aryl group Chemical group 0.000 claims description 58
- 239000010410 layer Substances 0.000 claims description 49
- 239000000126 substance Substances 0.000 claims description 36
- 239000012044 organic layer Substances 0.000 claims description 33
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 31
- 229910052805 deuterium Inorganic materials 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000000732 arylene group Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 14
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 239000002019 doping agent Substances 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
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- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
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- 125000005843 halogen group Chemical group 0.000 claims description 6
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- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000005264 aryl amine group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
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- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
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- 125000006836 terphenylene group Chemical group 0.000 claims description 2
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
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- 239000007787 solid Substances 0.000 description 51
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- 238000006243 chemical reaction Methods 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 38
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 32
- 239000012299 nitrogen atmosphere Substances 0.000 description 30
- 239000012153 distilled water Substances 0.000 description 25
- 238000010992 reflux Methods 0.000 description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- 238000002347 injection Methods 0.000 description 21
- 239000007924 injection Substances 0.000 description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 19
- 239000000706 filtrate Substances 0.000 description 18
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 16
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- JESHZQPNPCJVNG-UHFFFAOYSA-L magnesium;sulfite Chemical compound [Mg+2].[O-]S([O-])=O JESHZQPNPCJVNG-UHFFFAOYSA-L 0.000 description 13
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
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- 230000002194 synthesizing effect Effects 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 229940117389 dichlorobenzene Drugs 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- 238000005259 measurement Methods 0.000 description 6
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- 125000004306 triazinyl group Chemical group 0.000 description 6
- 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 5
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
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- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 4
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- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 3
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
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- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- LNGNZSMIUVQZOX-UHFFFAOYSA-L disodium;dioxido(sulfanylidene)-$l^{4}-sulfane Chemical compound [Na+].[Na+].[O-]S([O-])=S LNGNZSMIUVQZOX-UHFFFAOYSA-L 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
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- 229910052735 hafnium Inorganic materials 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- JWQLJPBJNSPKSG-UHFFFAOYSA-M magnesium;phenylbenzene;bromide Chemical compound [Mg+2].[Br-].C1=CC=CC=C1C1=CC=[C-]C=C1 JWQLJPBJNSPKSG-UHFFFAOYSA-M 0.000 description 2
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
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- 229910052726 zirconium Inorganic materials 0.000 description 2
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 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
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 1
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 1
- KUBSCXXKQGDPPD-UHFFFAOYSA-N 3-bromo-9-phenylcarbazole Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 KUBSCXXKQGDPPD-UHFFFAOYSA-N 0.000 description 1
- LTBWKAYPXIIVPC-UHFFFAOYSA-N 3-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC(Br)=CC=C3NC2=C1 LTBWKAYPXIIVPC-UHFFFAOYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- JUUBLVLOFUPMOY-UHFFFAOYSA-N 8-[4-(4,6-dinaphthalen-2-yl-1,3,5-triazin-2-yl)phenyl]quinoline Chemical compound C1=CN=C2C(C3=CC=C(C=C3)C=3N=C(N=C(N=3)C=3C=C4C=CC=CC4=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=CC2=C1 JUUBLVLOFUPMOY-UHFFFAOYSA-N 0.000 description 1
- GJWBRYKOJMOBHH-UHFFFAOYSA-N 9,9-dimethyl-n-[4-(9-phenylcarbazol-3-yl)phenyl]-n-(4-phenylphenyl)fluoren-2-amine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1N(C=1C=CC(=CC=1)C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C(C=C1)=CC=C1C1=CC=CC=C1 GJWBRYKOJMOBHH-UHFFFAOYSA-N 0.000 description 1
- MZYDBGLUVPLRKR-UHFFFAOYSA-N 9-(3-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 MZYDBGLUVPLRKR-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
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- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 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
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
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- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DLIJPAHLBJIQHE-UHFFFAOYSA-N butylphosphane Chemical compound CCCCP DLIJPAHLBJIQHE-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
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- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
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- 229940126214 compound 3 Drugs 0.000 description 1
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- 238000001816 cooling Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- TYKFGQULNYMDGJ-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C1=CC=C(C=2SC3=C(C21)C=CC=C3)B(O)O.C3=CC=C(C=2SC1=C(C23)C=CC=C1)B(O)O TYKFGQULNYMDGJ-UHFFFAOYSA-N 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 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 1
- 238000001035 drying Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 150000002220 fluorenes Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 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
- 239000000833 heterodimer 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
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 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
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- SRNAAWKKVXHYTI-UHFFFAOYSA-M magnesium;phenylbenzene;bromide Chemical compound [Mg+2].[Br-].C1=CC=CC=C1C1=CC=C[C-]=C1 SRNAAWKKVXHYTI-UHFFFAOYSA-M 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WRGLZAJBHUOPFO-UHFFFAOYSA-N methyl 3-oxo-3-phenylpropanoate Chemical compound COC(=O)CC(=O)C1=CC=CC=C1 WRGLZAJBHUOPFO-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- MESMXXUBQDBBSR-UHFFFAOYSA-N n,9-diphenyl-n-[4-[4-(n-(9-phenylcarbazol-3-yl)anilino)phenyl]phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=C1 MESMXXUBQDBBSR-UHFFFAOYSA-N 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
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 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
- 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
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 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
- 239000008096 xylene Substances 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/008—Triarylamine dyes containing no other chromophores
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Description
X1〜X12は、それぞれ独立に、N、C、またはCRaであり、
X1〜X6のうちの少なくとも1つは、Nであり、
X7〜X12のうちの少なくとも1つは、Nであり、
Raは、それぞれ独立に、水素、重水素、置換もしくは非置換のC1〜C30アルキル基、置換もしくは非置換のC1〜C30アルケニル基、置換もしくは非置換のC1〜C30アルキニル基、置換もしくは非置換のC6〜C30アリール基、置換もしくは非置換のC6〜C30アリールオキシ基、置換もしくは非置換のC6〜C30アリールチオ基、置換もしくは非置換のC2〜C30ヘテロアリール基、ヒドロキシル基、チオール基、またはこれらの組み合わせであり、
Raは、それぞれ独立に存在するか、隣接したRaは、互いに連結されて環を形成し、
L1は、重水素、C1〜C40シリル基、C1〜C30アルキル基、C3〜C30シクロアルキル基、C2〜C30ヘテロシクロアルキル基、またはC6〜C30アリール基で置換されているか非置換のC6〜C30アリーレン基であり;
L2〜L4は、それぞれ独立に、単結合、置換もしくは非置換のC6〜C30アリーレン基、または置換もしくは非置換のC2〜C30ヘテロアリーレン基であり、
Ar1〜Ar3は、それぞれ独立に、置換もしくは非置換のC6〜C30アリール基、置換もしくは非置換のC2〜C30ヘテロ環基、またはこれらの組み合わせであり、
前記化学式1および2の「置換」は、別途の定義がない限り、少なくとも1つの水素が重水素、ハロゲン基、ヒドロキシル基、アミノ基、C1〜C30アミン基、C6〜C30アリールアミン基、ニトロ基、C1〜C40シリル基、C1〜C30アルキル基、C3〜C30シクロアルキル基、C2〜C30ヘテロシクロアルキル基、C6〜C30アリール基、C2〜C30ヘテロ環基、C1〜C20アルコキシ基、C1〜C10トリフルオロアルキル基またはシアノ基で置換されていることを意味する。
炭化水素芳香族部分のすべての元素がp軌道を有しかつ、これらp軌道が共役(conjugation)を形成している形態、例えば、フェニル基、ナフチル基などを含み、
2以上の炭化水素芳香族部分がσ結合により連結された形態、例えば、ビフェニル基、ターフェニル基、クォーターフェニル基などを含み、
2以上の炭化水素芳香族部分が直接または間接的に縮合された非芳香族縮合環も含むことができる。例えば、フルオレニル基などが挙げられる。
L1は、重水素、C1〜C40シリル基、C1〜C30アルキル基、C3〜C30シクロアルキル基、C2〜C30ヘテロシクロアルキル基、またはC6〜C30アリール基で置換されているか非置換のC6〜C30アリーレン基であり;
L2〜L4は、それぞれ独立に、単結合、置換もしくは非置換のC6〜C30アリーレン基、または置換もしくは非置換のC2〜C30ヘテロアリーレン基であり、
Ar1〜Ar3は、それぞれ独立に、置換もしくは非置換のC6〜C30アリール基、置換もしくは非置換のC2〜C30ヘテロ環基、またはこれらの組み合わせであり、
前記化学式1および2の「置換」は、別途の定義がない限り、少なくとも1つの水素が重水素、ハロゲン基、ヒドロキシル基、アミノ基、C1〜C30アミン基、C6〜C30アリールアミン基、ニトロ基、C1〜C40シリル基、C1〜C30アルキル基、C3〜C30シクロアルキル基、C2〜C30ヘテロシクロアルキル基、C6〜C30アリール基、C2〜C30ヘテロ環基、C1〜C20アルコキシ基、C1〜C10トリフルオロアルキル基またはシアノ基で置換されていることを意味する。
具体的には、水素、または置換もしくは非置換のC6〜C30アリール基であってもよいし、
さらに具体的には、水素、置換もしくは非置換のフェニル基、置換もしくは非置換のビフェニル基、置換もしくは非置換のターフェニル基、置換もしくは非置換のクォーターフェニル基、置換もしくは非置換のナフチル基、置換もしくは非置換のアントラセニル基、置換もしくは非置換のトリフェニレン基、置換もしくは非置換のフェナントレニル基、置換もしくは非置換のピレニル基であってもよい。
前記隣接したRaは、互いに連結されて置換もしくは非置換のキナゾリニル基を形成してもよい。
さらに具体的には、X1〜X6から構成されたヘテロ環基は、ピリミジニル基、またはトリアジニル基であってもよく、X7〜X12から構成されたヘテロ環基も、ピリミジニル基、またはトリアジニル基であってもよい。
前記C6〜C30アリール基は、置換もしくは非置換のフェニル基、置換もしくは非置換のビフェニル基、置換もしくは非置換のターフェニル基、置換もしくは非置換のクォーターフェニル基、置換もしくは非置換のナフチル基、置換もしくは非置換のアントラセニル基、置換もしくは非置換のフルオレニル基、置換もしくは非置換のトリフェニレン基、または置換もしくは非置換のフェナントレニル基であってもよい。また、一例において、Raの「置換もしくは非置換の」における「置換」は、重水素、C1〜C10アルキル基、C6〜20アリール基、またはピリミジン基であってもよい。
例えば、単結合、置換もしくは非置換のフェニレン基、置換もしくは非置換のビフェニレン基、置換もしくは非置換のナフチル基、置換もしくは非置換のフルオレニル基、置換もしくは非置換のピリジニル基、置換もしくは非置換のピリミジニル基、置換もしくは非置換のキノリニル基、またはこれらの組み合わせであってもよい。
さらに具体的には、置換もしくは非置換のフェニル基、置換もしくは非置換のビフェニル基、置換もしくは非置換のターフェニル基、置換もしくは非置換のクォーターフェニル基、置換もしくは非置換のナフチル基、置換もしくは非置換のフルオレニル基、置換もしくは非置換のカルバゾリル基、置換もしくは非置換のジベンゾフラニル基、置換もしくは非置換のジベンゾチオフェニル基、置換もしくは非置換のアントラセニル基、置換もしくは非置換のフェナントレニル基、置換もしくは非置換のトリフェニレン基、置換もしくは非置換のキノリニル基、置換もしくは非置換のピリジニル基、置換もしくは非置換のピリミジニル基、置換もしくは非置換のチオフェニル基、またはこれらの組み合わせであってもよい。
ここで、「置換」は、前述した通りである。
合成例1:化合物1の合成
a)中間体1−1の合成
a)中間体3−1の合成
a)中間体100−1の合成
a)中間体4−2の合成
a)中間体16−2の合成
合成例7:化合物126の合成
a)中間体140−1の合成
a)中間体113−3の合成
a)中間体q−3の合成
合成例Ad−2:化合物180の合成
合成例Ad−1のa)中間体q−3の合成段階において「4−ビフェニルボロン酸」の代わりに「フェニルボロン酸」を用い、合成例Ad−1の合成法を適切に用いて化合物180を合成した。
合成例Ad−1のa)中間体q−3の合成段階において「4−ビフェニルボロン酸」の代わりに「フェニルボロン酸」を用い、合成例Ad−1の合成法を適切に用いて化合物183を合成した。
合成例Ad−1のa)中間体q−3の合成段階において「4−ビフェニルボロン酸」の代わりに「フェニルボロン酸」を用い、b)段階において「2−クロロフェニルボロン酸」の代わりに「2−クロロ−2’−ビフェニルボロン酸」を用い、合成例Ad−1の合成法を適切に用いて化合物190を合成した。
中間体M−1の合成
合成例13:化合物A−10の合成
実施例1
ITO(Indium tin oxide)が1500Åの厚さに薄膜コーティングされたガラス基板を、蒸留水で超音波洗浄した。蒸留水洗浄が終わると、イソプロピルアルコール、アセトン、メタノールなどの溶剤で超音波洗浄をし乾燥させた後、プラズマ洗浄機に移送させた後、酸素プラズマを用いて前記基板を10分間洗浄した後、真空蒸着機に基板を移送した。このように準備されたITO透明電極を陽極として用いて、ITO基板の上部に化合物Aを真空蒸着して700Åの厚さの正孔注入層を形成し、前記正孔注入層の上部に化合物Bを50Åの厚さに蒸着した後、化合物Cを1020Åの厚さに蒸着して正孔輸送層を形成した。正孔輸送層の上部に合成例1の化合物1および合成例10の化合物A−414を同時にホストとして用い、ドーパントとしてトリス(2−フェニルピリジン)イリジウム(III)[Ir(ppy)3]を10wt%でドーピングして、真空蒸着で400Åの厚さの発光層を形成した。ここで、化合物1と化合物A−414とは3:7の重量比で使用され、下記の実施例の場合、別途に比率を記述した。次に、前記発光層の上部に化合物DとLiqとを同時に1:1の比率で真空蒸着して、300Åの厚さの電子輸送層を形成し、前記電子輸送層の上部にLiq15ÅとAl 1200Åとを順次に真空蒸着して陰極を形成することによって、有機発光素子を作製した。
化合物B:1,4,5,8,9,11−hexaazatriphenylene−hexacarbonitrile(HAT−CN)
化合物C:N−(biphenyl−4−yl)−9,9−dimethyl−N−(4−(9−phenyl−9H−carbazol−3−yl)phenyl)−9H−fluoren−2−amine
化合物D:8−(4−(4,6−di(naphthalen−2−yl)−1,3,5−triazin−2−yl)phenyl)quinoline。
下記表1に示すように、第1ホストおよび第2ホストを当該比率で用いて、前記実施例1と同様の方法で実施例2〜実施例16の有機発光素子を作製した。
下記表1に示すように、第1ホストを単独ホストとして用いて、前記実施例1と同様の方法で比較例1〜10の有機発光素子を作製した。
化合物A−414と下記の比較例の化合物Iをホストとして5:5の比率で用いて、実施例1と同様の方法で素子を作製した。
化合物1とmCP(1,3−Bis(N−carbazolyl)benzene)をホストとして5:5の比率で用いて、実施例1と同様の方法で素子を作製した。
実施例17
合成例Ad−1の化合物181および合成例23の化合物C31をそれぞれ3:7の重量比で混合して同時にホストとして用い、ドーパントとして[Ir(piq)2acac]を5wt%でドーピングして発光層を形成したことを除けば、前記実施例1と同様の方法で実施例17の有機発光素子を作製した。
下記表2に示すように、第1ホストおよび第2ホストを当該比率で用いて、前記実施例17と同様の方法で実施例18〜実施例20の有機発光素子を作製した。
下記表2に示すように、第1ホストを単独ホストとして用いて、前記実施例17と同様の方法で比較例13〜比較例15の有機発光素子を作製した。
前記実施例1〜20、および比較例1〜15による有機発光素子の発光効率および寿命特性を評価した。具体的な測定方法は下記の通りであり、その結果は表1および表2の通りである。
製造された有機発光素子に対して、電圧を0Vから10Vまで上昇させながら、電流−電圧計(Keithley2400)を用いて単位素子に流れる電流値を測定し、測定された電流値を面積で割って結果を得た。
製造された有機発光素子に対して、電圧を0Vから10Vまで上昇させながら、輝度計(Minolta Cs−1000A)を用いてその時の輝度を測定して結果を得た。
前記(1)および(2)から測定された輝度と電流密度および電圧を用いて同一電流密度(10mA/cm2)の電流効率(cd/A)を計算した。
製造された有機発光素子に対して、ポーラロニックス寿命測定システムを用いて、実施例1〜20および比較例1〜比較例15の素子を、初期輝度(cd/m2)を5000cd/m2で発光させ、時間の経過に応じた輝度の減少を測定して、初期輝度対比90%に輝度が減少した時点をT90寿命として測定した。
電流−電圧計(Keithley2400)を用いて15mA/cm2で各素子の駆動電圧を測定し、その結果を下記表1および表2に記載した。
105 有機層、
110 カソード、
120 アノード、
130 発光層、
140 補助層。
Claims (12)
- 下記化学式1で表される少なくとも1種の第1化合物;
下記化学式2で表される少なくとも1種の第2化合物;および
燐光ドーパント、を含む、有機光電子素子用組成物:
X1〜X12は、それぞれ独立に、N、C、またはCRaであり、
X1〜X6のうちの少なくとも2つは、Nであり、
X7〜X12のうちの少なくとも2つは、Nであり、
Raは、それぞれ独立に、水素、重水素、置換もしくは非置換のC1〜C30アルキル基、置換もしくは非置換のC1〜C30アルケニル基、置換もしくは非置換のC1〜C30アルキニル基、置換もしくは非置換のC6〜C30アリール基、置換もしくは非置換のC6〜C30アリールオキシ基、置換もしくは非置換のC6〜C30アリールチオ基、置換もしくは非置換のC2〜C30ヘテロアリール基、ヒドロキシル基、チオール基、またはこれらの組み合わせであり、
Raは、それぞれ独立に存在するか、隣接したRaは、互いに連結されて環を形成し、
L1は、重水素、C1〜C40シリル基、C1〜C30アルキル基、C3〜C30シクロアルキル基、C2〜C30ヘテロシクロアルキル基、またはC6〜C30アリール基で置換されているか非置換のC6〜C30アリーレン基であり;
L2〜L4は、それぞれ独立に、単結合、置換もしくは非置換のC6〜C30アリーレン基、または置換もしくは非置換のC2〜C30ヘテロアリーレン基であり、
Ar1〜Ar3は、それぞれ独立に、置換もしくは非置換のC6〜C30アリール基、置換もしくは非置換のC2〜C30ヘテロ環基、またはこれらの組み合わせであり、
前記化学式1および2の「置換」は、別途の定義がない限り、少なくとも1つの水素が重水素、ハロゲン基、ヒドロキシル基、アミノ基、C1〜C30アミン基、C6〜C30アリールアミン基、ニトロ基、C1〜C40シリル基、C1〜C30アルキル基、C3〜C30シクロアルキル基、C2〜C30ヘテロシクロアルキル基、C6〜C30アリール基、C2〜C30ヘテロ環基、C1〜C20アルコキシ基、C1〜C10トリフルオロアルキル基またはシアノ基で置換されていることを意味する。 - 前記化学式1は、下記化学式1−I〜化学式1−IVのうちのいずれか1つで表される、請求項1に記載の有機光電子素子用組成物:
Zは、それぞれ独立に、N、またはCRaであり、
Zを含むそれぞれの環において少なくとも2つのZは、Nであり、
Ra、Ra1〜Ra4、Rc、Rd、Re、Rf、Rg、およびRhは、それぞれ独立に、水素、重水素、置換もしくは非置換のC1〜C30アルキル基、置換もしくは非置換のC6〜C30アリール基、置換もしくは非置換のC2〜C30ヘテロアリール基、またはこれらの組み合わせであり、
L1は、重水素、C1〜C40シリル基、C1〜C30アルキル基、C3〜C30シクロアルキル基、C2〜C30ヘテロシクロアルキル基、またはC6〜C30アリール基で置換されているか非置換のC6〜C30アリーレン基であり、
ここで、「置換」は、請求項1で定義した通りである。 - 前記L1は、重水素、C1〜C40シリル基、C1〜C30アルキル基、もしくはC6〜C30アリール基で置換されているか非置換のフェニレン基;
重水素、C1〜C40シリル基、C1〜C30アルキル基、もしくはC6〜C30アリール基で置換されているか非置換のビフェニレン基;
重水素、C1〜C40シリル基、C1〜C30アルキル基、もしくはC6〜C30アリール基で置換されているか非置換のターフェニレン基;または
重水素、C1〜C40シリル基、C1〜C30アルキル基、もしくはC6〜C30アリール基で置換されているか非置換のクォーターフェニレン基である、請求項1または2に記載の有機光電子素子用組成物。 - 前記L1は、置換されているか非置換の下記グループ2に挙げられた連結基から選択される、請求項1または2に記載の有機光電子素子用組成物:
- 前記化学式1のX1〜X12は、それぞれ独立に、N、C、またはCRaであり、
X1〜X6のうちの3つは、Nであり、
X7〜X12のうちの2つ〜3つは、Nであり、
Raは、それぞれ独立に、水素、重水素、置換もしくは非置換のC1〜C30アルキル基、置換もしくは非置換のC6〜C30アリール基、置換もしくは非置換のC2〜C30ヘテロアリール基、またはこれらの組み合わせであり、
L1は、重水素、C1〜C30アルキル基、またはC6〜C30アリール基で置換されているか非置換のC6〜C30アリーレン基であり、
ここで、「置換」は、別途の定義がない限り、少なくとも1つの水素が重水素、ハロゲン基、ヒドロキシル基、C1〜C40シリル基、C1〜C30アルキル基、C3〜C30シクロアルキル基、C2〜C30ヘテロシクロアルキル基、C6〜C30アリール基、またはC2〜C30ヘテロ環基で置換されている、請求項1〜4のいずれか1項に記載の有機光電子素子用組成物。 - 前記Raは、置換もしくは非置換のC6〜C30アリール基であり、
前記C6〜C30アリール基は、置換もしくは非置換のフェニル基、置換もしくは非置換のビフェニル基、置換もしくは非置換のターフェニル基、置換もしくは非置換のクォーターフェニル基、置換もしくは非置換のナフチル基、置換もしくは非置換のアントラセニル基、置換もしくは非置換のフルオレニル基、置換もしくは非置換のトリフェニレン基、または置換もしくは非置換のフェナントレニル基である、請求項5に記載の有機光電子素子用組成物。 - 前記化学式2のL2〜L4は、それぞれ独立に、単結合、置換もしくは非置換のフェニレン基、置換もしくは非置換のビフェニレン基、置換もしくは非置換のナフチル基、置換もしくは非置換のフルオレニル基、置換もしくは非置換のピリジニル基、置換もしくは非置換のピリミジニル基、置換もしくは非置換のキノリニル基、またはこれらの組み合わせであり、
Ar1〜Ar3は、それぞれ独立に、置換もしくは非置換のフェニル基、置換もしくは非置換のビフェニル基、置換もしくは非置換のターフェニル基、置換もしくは非置換のクォーターフェニル基、置換もしくは非置換のナフチル基、置換もしくは非置換のフルオレニル基、置換もしくは非置換のカルバゾリル基、置換もしくは非置換のジベンゾフラニル基、置換もしくは非置換のジベンゾチオフェニル基、置換もしくは非置換のアントラセニル基、置換もしくは非置換のフェナントレニル基、置換もしくは非置換のトリフェニレン基、置換もしくは非置換のキノリニル基、置換もしくは非置換のピリジニル基、置換もしくは非置換のピリミジニル基、置換もしくは非置換のチオフェニル基、またはこれらの組み合わせである、請求項1〜6のいずれか1項に記載の有機光電子素子用組成物。 - 前記化学式2のAr1〜Ar3は、置換もしくは非置換の下記グループ4に挙げられた基から選択される、請求項7に記載の有機光電子素子用組成物:
- 前記第1化合物は、下記化学式1−Iaまたは化学式1−IVaで表され、
前記第2化合物は、前記化学式2のL2〜L4がそれぞれ独立に、単結合、または置換もしくは非置換のフェニレン基であり、Ar1〜Ar3がそれぞれ独立に、置換もしくは非置換のC6〜C30アリール基、または置換もしくは非置換のC2〜C30ヘテロ環基であるものの、Ar1〜Ar3のうちの少なくとも1つは、置換もしくは非置換のC2〜C30ヘテロ環基である、請求項1〜8のいずれか1項に記載の有機光電子素子用組成物:
Z1〜Z6は、それぞれ独立に、N、またはCRaであり、
Z1〜Z3のうちの少なくとも2つは、Nであり、
Z4〜Z6のうちの少なくとも2つは、Nであり、
Ra、およびRa1〜Ra4は、それぞれ独立に、水素、または置換もしくは非置換のC6〜C30アリール基であり、
L1は、重水素、C1〜C30アルキル基、またはC6〜C30アリール基で置換されているか非置換のC6〜C30アリーレン基であり、
ここで、「置換」は、請求項1で定義した通りである。 - 互いに対向するアノードおよびカソードと、
前記アノードと前記カソードとの間に位置する少なくとも1層の有機層とを含み、
前記有機層は、請求項1〜9のいずれか1項に記載の有機光電子素子用組成物を含む有機光電子素子。 - 前記有機層は、発光層を含み、
前記発光層は、前記有機光電子素子用組成物を含む、請求項10に記載の有機光電子素子。 - 請求項10または11に記載の有機光電子素子を含む表示装置。
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KR101602533B1 (ko) * | 2013-09-30 | 2016-03-10 | 주식회사 엘지화학 | 헤테로환 화합물 및 이를 포함하는 유기 발광 소자 |
KR102093186B1 (ko) * | 2013-12-03 | 2020-03-25 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
CN103985822B (zh) * | 2014-05-30 | 2017-05-10 | 广州华睿光电材料有限公司 | 有机混合物、包含其的组合物、有机电子器件及应用 |
KR102054277B1 (ko) * | 2016-07-29 | 2019-12-10 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 |
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- 2016-10-10 EP EP16857700.5A patent/EP3366749B1/en active Active
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EP3366749A1 (en) | 2018-08-29 |
US20180301635A1 (en) | 2018-10-18 |
KR20170048159A (ko) | 2017-05-08 |
CN108350351B (zh) | 2020-09-15 |
EP3366749B1 (en) | 2021-12-08 |
EP3366749A4 (en) | 2019-06-26 |
JP2019501516A (ja) | 2019-01-17 |
CN108350351A (zh) | 2018-07-31 |
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