WO2019132399A1 - 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 - Google Patents
유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 Download PDFInfo
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- WO2019132399A1 WO2019132399A1 PCT/KR2018/016246 KR2018016246W WO2019132399A1 WO 2019132399 A1 WO2019132399 A1 WO 2019132399A1 KR 2018016246 W KR2018016246 W KR 2018016246W WO 2019132399 A1 WO2019132399 A1 WO 2019132399A1
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- 230000005693 optoelectronics Effects 0.000 title claims abstract description 98
- 150000001875 compounds Chemical class 0.000 title claims abstract description 93
- 239000000203 mixture Substances 0.000 title claims abstract description 37
- 239000000126 substance Substances 0.000 claims abstract description 11
- 239000010410 layer Substances 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 23
- 229910052805 deuterium Inorganic materials 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- 239000012044 organic layer Substances 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 17
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 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 claims description 6
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- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
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- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 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
- 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
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 229910052775 Thulium 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
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 125000003342 alkenyl 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
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution 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
- 150000001555 benzenes Chemical class 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
- 239000004305 biphenyl Chemical group 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
- GJPFCLXEIGJYKN-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2cc(-c(cc3)cc4c3c(cccc3)c3[o]4)c3[o]c4ccccc4c3c2)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2cc(-c(cc3)cc4c3c(cccc3)c3[o]4)c3[o]c4ccccc4c3c2)nc(-c2ccccc2)n1 GJPFCLXEIGJYKN-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
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([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
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- FQENSZQWKVWYPA-UHFFFAOYSA-N dibenzofuran-3-ylboronic acid Chemical compound C1=CC=C2C3=CC=C(B(O)O)C=C3OC2=C1 FQENSZQWKVWYPA-UHFFFAOYSA-N 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical class C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 238000002523 gelfiltration Methods 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
- 229910052735 hafnium Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 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
- 230000003993 interaction Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002527 isonitriles Chemical class 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 150000003854 isothiazoles Chemical class 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 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
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 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
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 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
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- C—CHEMISTRY; METALLURGY
- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
Definitions
- compositions for organic optoelectronic devices compositions for organic optoelectronic devices, organic optoelectronic devices and display devices.
- An organic optoelectronic diode is a device that can switch between electrical and optical energy.
- Organic optoelectronic devices can be roughly classified into two types according to the operating principle.
- One is an optoelectronic device in which an exciton formed by light energy is separated into an electron and a hole, and the electrons and the holes are transferred to different electrodes to generate electric energy
- the other is a voltage / Emitting device that generates light energy from energy.
- organic optoelectronic devices examples include organic optoelectronic devices, organic light emitting devices, organic solar cells, and organic photo conductor drums.
- the organic light emitting diode is a device that converts electrical energy into light by applying an electric current to the organic light emitting material.
- the organic light emitting diode usually has a structure in which electrons are inserted between an anode and a cathode.
- the organic layer may include a light emitting layer and an optional auxiliary layer.
- the auxiliary layer may include, for example, a hole injecting layer, a hole transporting layer, an electron blocking layer, an electron transporting layer, an electron injecting layer, At least one layer selected from the group consisting of
- the performance of the organic light emitting device is greatly influenced by the characteristics of the organic layer, and the organic light emitting device is highly affected by the organic material contained in the organic layer.
- One embodiment provides a compound for an organic optoelectronic device capable of implementing a high-efficiency and long-lived organic optoelectronic device.
- compositions for organic optoelectronic devices comprising the composition.
- Another embodiment provides an organic optoelectronic device and a display device including the composition for the organic optoelectronic device.
- a compound for an organic optoelectronic device represented by the following formula (1).
- X < 1 > is 0 or Y
- To II 8 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted (having 1 to 10 0 alkyl groups, substituted or unsubstituted 06 to 020 aryl groups, or substituted or unsubstituted 02 to 030 heterocyclic groups ,
- One of the valencies II 6 and II 7 is a substituted or unsubstituted 02 to 030 heterocyclic group containing at least one nitrogen atom,
- X 2 is 0 or
- ⁇ To 3 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted 0 ⁇ to 010 alkyl group, a substituted or unsubstituted € 6 to 020 an aryl group, or a substituted or unsubstituted 02 to 030 heterocyclic group .
- composition for an organic optoelectronic device including the compound for an organic optoelectronic device.
- the organic light emitting device includes an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, wherein the organic layer is a composition for a compound for organic optoelectronic devices or a composition for organic optoelectronic devices Organic photovoltaic devices.
- a display device including the organic optoelectronic device.
- FIG. 1 and 2 are cross-sectional views illustrating an organic light emitting device according to one embodiment.
- At least one hydrogen in the substituent or compound is replaced by a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted 2019/132399 1 »(: 1 ⁇ ⁇ 2018/016246
- " substituted " means that at least one hydrogen in the substituent or compound is deuterium, Substituted with 0 to 30 alkyl groups, (: 1 to 10 alkylsilyl groups, 06 to 030 arylsilyl groups, 03 to 030 cycloalkyl groups, 3 to 030 heterocycloalkyl groups, 06 to 030 aryl groups, 02 to 030 heteroaryl groups . Further, in a specific example of the present invention, " substituted " means that at least one hydrogen in the substituent or compound is deuterium, An alkyl group, a C6 to O30 aryl group, or a C2 to O30
- a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted heteroaryl group is A substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted heteroaryl group.
- Substituent means that at least one hydrogen in the substituent or the compound is substituted with deuterium , ( 1 : 05 alkyl group, 06 to 018 a 1 group, dibenzofuranyl group, or dibenzothiophenyl group)
- " substituted " means that at least one hydrogen in the substituent or the compound is substituted with at least one substituent selected from the group consisting of deuterium, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, , Dibenzofuranyl group, or dibenzothiophenyl group.
- hetero means, unless otherwise defined, one to three heteroatoms selected from the group consisting of the substituents 0, 3, and 4 in one functional group, with the remainder being carbon.
- the alkyl group may be a "saturated alkyl chain " 71) group which does not contain any subordinate bonds or triple bonds.
- the alkyl group may be an alkyl group having 1 to 30 carbon atoms. More specifically, the alkyl group is
- C4 alkyl group means that 1 to 4 carbon atoms are contained in the alkyl chain and is selected from the group consisting of methyl, ethyl, propyl, iso-propyl, 11-butyl, iso-butyl,
- alkyl group examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, 2019/132399 1 »(: 1 ⁇ ⁇ 2018/016246
- 5-butyl group, isobutyl group, t - means, such as a butyl group, a pentyl group, nuclear group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cycloalkyl group nucleus.
- " refers to a grouping of groups having one or more hydrocarbon aromatic moieties
- a structure in which two or more hydrocarbon aromatic moieties are connected through a sigma bond such as a biphenyl group, a terphenyl group, a quarter-phenyl group,
- aryl group may be monocyclic, polycyclic or fused ring polycyclic (i. E.
- heterocyclic group " is a superordinate concept including a heteroaryl group, and includes N, O, or S in the cyclic compound such as an aryl group, a cycloalkyl group, a fused ring thereof, S, P, and Si.
- the heterocyclic group may contain one or more heteroatoms in whole or in each ring. have.
- heteroaryl group means that at least one heteroatom selected from the group consisting of N, O, S, P, and Si is contained in the aryl group. Two or more heteroaryl groups are bonded through a sigma bond When the heteroaryl group includes two or more rings, two or more rings may be fused to each other.
- each ring may contain 1 to 3 of the above heteroatoms.
- the substituted or unsubstituted C6 to C30 aryl group may be substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthrenyl group, A substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted 0- A substituted or unsubstituted phenyl group, 2019/132399 1 »(: 1 ⁇ ⁇ 2018/016246
- the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group,
- the hole property refers to a property of forming holes by donating electrons when an electric field is applied. It has a conduction property along the HOMO level so that the holes formed in the anode are injected into the light emitting layer, Quot; refers to a property that facilitates the movement of the hole to the anode and the movement of the hole in the light emitting layer.
- the electron characteristic refers to a characteristic that electrons can be received when an electric field is applied.
- the electron characteristic has a conduction characteristic along the LUMO level to inject electrons formed in the cathode into the light emitting layer, move electrons formed in the light emitting layer to the cathode, Of the present invention.
- the composition for an organic optoelectronic device according to an embodiment will be described. 2019/132399 1 »(: 1 ⁇ ⁇ 2018/016246
- the compounds for organic optoelectronic devices according to embodiments of the present invention can be represented by the following formula (1).
- X < 1 > is 0 or,
- And to II 8 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted 01 to 010 alkyl group, a substituted or unsubstituted aryl group, 06 to 020, or a substituted or unsubstituted 02 to 030 heterocyclic group,
- the mitmyo 7 popularly least one is a substituted or unsubstituted 02 to 030 ring heterocyclic group comprising from one or more sources of nitrogen,
- Each of Formulas 9 to 13 is independently hydrogen, deuterium, cyano, substituted or unsubstituted 01 to 010 alkyl group, substituted or unsubstituted 06 to 020 aryl group, or substituted or unsubstituted 02 to 030 heterocyclic group .
- the compound represented by Formula 1 may serve as an electron injecting, electron transporting or luminescent material in an organic optoelectronic device.
- a driving voltage can be lowered and an organic optoelectronic device with improved efficiency can be manufactured.
- the compound having an asymmetric structure can suppress the decomposition upon deposition.
- one of the substituents 6 and 7 is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted Or an unsubstituted quinazolinyl group or a substituted or unsubstituted benzothienopyrimidinyl group.
- X 3 to X 5 are each independently or a group of the formula:
- X 3 to X 5 are also at least one
- R 14 and R 5 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted 01 to 010 alkyl group, substituted or unsubstituted 06 to 020 aryl group, or substituted or unsubstituted 02 to 030 heterocyclic group.
- X 3 to X 5 may be more than two.
- each of the moieties 14 and 5 may independently be any one substituent selected from the following Group I. 2019/132399 1 »(: 1 ⁇ ⁇ 2018/016246
- the formula (2) may be represented by the following formula (2-1) or (2-2).
- X < 2 > are each independently 0 or,
- Each of Formulas 9 to II 13 is independently hydrogen, deuterium, cyano, substituted or unsubstituted 01 to 010 alkyl group, substituted or unsubstituted 06 to 020 aryl group, or substituted or unsubstituted 02 to 030 heterocyclic group .
- the compound for organic optoelectronic devices represented by Formula 1 may be selected from the compounds listed in Group 1 below, but is not limited thereto.
- the above-mentioned compounds for organic optoelectronic devices can be applied to organic optoelectronic devices alone or in combination with other compounds for organic optoelectronic devices.
- the above-mentioned compound for an organic optoelectronic device is used alone or in combination with another compound for an organic optoelectronic device, it can be applied in the form of a composition.
- the present invention provides a composition for an organic optoelectronic device including the compound for an organic optoelectronic device (compound for a first organic optoelectronic device) represented by the above-mentioned formula (1).
- the present invention can provide a composition for an organic electronic device comprising the compound for the first organic optoelectronic device and the compound represented by the following formula (4) (compound for a second organic optoelectronic device).
- each independently represents a single bond, a substituted or unsubstituted 06 to 030 arylene group, a substituted or unsubstituted 02 to 030 heteroarylene group, or a combination thereof,
- 1 and 2 each independently represent a substituted or unsubstituted 06 to O30 aryl group, a substituted 2019/132399 1 »(: 1 ⁇ ⁇ 2018/016246
- 1 11 is one of 0 to 2 water.
- V 1 and V in Formula 4 may each independently be a single bond, or a substituted or unsubstituted 06 to 018 arylene group.
- the show and show in the formula (4) independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, A substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, an unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, A substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a
- each of 6 to 1 of Formula 4 may be independently hydrogen, deuterium, or a substituted or unsubstituted 06 to (12 aryl) group.
- 111 in Formula 4 may be 0 or 1.
- Formula 4 is one of the structures listed in the following Group II, It can be one of the substituents listed in the above.
- Formula 4 is represented by 0-8 of Group II, And * - - 2 may be represented by one of 6-1 to 4 of the group III. More specifically,
- the present invention also relates to an organic electroluminescent device comprising a compound for the first organic optoelectronic device and a compound consisting of a combination of a moiety represented by the following formula (5) and a moiety represented by the following formula (6)
- ', And 4 are each independently a single bond, substituted or unsubstituted 06 to 30 aryl tengi, substituted or unsubstituted 02 to a combination of 030-heteroaryl group, or a control, shows 1 _ 3 and 4 coming each independently) -, a monocyclic or an unsubstituted 06 to 030 aryl group, a substituted or unsubstituted 02 to 030 heterocyclic group, or a combination thereof,
- 2 to II 25 each independently represent hydrogen, deuterium, a substituted or unsubstituted 01 to 020 alkyl group, a substituted or unsubstituted 06 to 050 aryl group, a substituted or unsubstituted 02 to
- Substituted or unsubstituted C1 to C10 alkyl groups substituted or unsubstituted C6 to C12 aryl groups, substituted or unsubstituted C1 to C12 heterocyclic groups, or combinations thereof.
- the show # and show / may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a combination thereof.
- one of the above 3 and / or the above may include a substituted or unsubstituted carbazole group.
- the second organic compound composed of a combination of moieties may be represented by one of the following formulas (7-1 to 7-5) depending on the bonding position. 2019/132399 1 »(: 1/10 ⁇ 018/016246
- each independently represents a single bond, a substituted or unsubstituted 06 to 030 arylene group, a substituted or unsubstituted 02 to 030 heteroarylene group or a combination thereof, and each of the following groups 3 and 4 independently represents a substituted or unsubstituted 06 A substituted or unsubstituted C2 to O30 aryl group, a substituted or unsubstituted C2 to O30 heterocyclic group,
- 2 to 5 are each independently hydrogen, deuterium, a substituted or unsubstituted 01 to 020 alkyl group, a substituted or unsubstituted 06 to 050 aryl group, a substituted or unsubstituted C2 to 50 heterocyclic group, or combinations thereof. 2019/132399 1 »(: 1/10 ⁇ 018/016246
- one of the groups of 3 and 4 in the formulas (7-1) to (7-5) may be a substituent having a hole property, and may include, for example, a substituted or unsubstituted carbazole group.
- the compound for a second organic optoelectronic device composed of a combination of the moiety represented by Formula 5 and the moiety represented by Formula 6 may be, for example, a compound listed in Group II below. [Group IV] In the specific compounds described in [IV] below, to be.)
- composition according to an embodiment may be applied to an organic layer of an organic optoelectronic device, for example, to a light emitting layer of an organic optoelectronic device, and the compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device may be used as a host Can play a role.
- the compound for the first organic optoelectronic device may be a compound having a bipolar characteristic having a relatively high electron characteristic
- the compound for the second organic optoelectronic device may have a bipolar characteristic having a relatively high hole characteristic. Used in combination with compounds for optoelectronic devices to improve charge mobility and stability.
- the luminous efficiency and lifetime characteristics can be further improved.
- the recombination of the carriers occurs at the interface between the light emitting layer and the electron transporting layer or the hole transporting layer, and the formation of the excitons is relatively increased.
- the light emitting layer in the molecule excitons and transporting layer due to interaction with the surface of the charge efficiency is sharply falling roll-off ⁇ 0 11 - (: 0 phenomenon occurs, and is also rapidly dropped emission life characteristics.
- the compound for a first organic optoelectronic device and the compound for a second organic optoelectronic device are simultaneously introduced into a light emitting layer as a host compound,
- the carrier in the light emitting layer is formed so that the light emitting region is not shifted to either one of the hole transporting layers 2019/132399 1 »(: 1 ⁇ ⁇ 2018/016246
- the compound for the first organic optoelectronic device mentioned above can be prepared by various combinations of the compounds for the organic optoelectronic device.
- the compound for the second organic optoelectronic device can be used in the light emitting layer together with the compound for the first organic optoelectronic device to improve the drift voltage, luminescence efficiency and lifetime characteristics by increasing the residual mobility and increasing the stability.
- the compound for the first organic optoelectronic device of the present invention can be used in a composition of about 1: 9 to 9: 1, 2: 8 to 8: 2, 3: 7 to 7: 4, and 5: 5, and specifically 1: 9 to 8: 2, 1: 9 to 7: 3, 1: 9 to 6: 4,
- composition for an organic optoelectronic device can be used as a host of a green or red organic light emitting device.
- the compound or composition for an organic optoelectronic device may further include at least one organic compound in addition to the compound for another organic optoelectronic device.
- the compound for the first organic optoelectronic device Project 2 The composition including the compound for an organic optoelectronic device may further include a dopant.
- the dopant may be a red, green or blue dopant, for example a red or green phosphorescent dopant.
- the dopant may be a material that emits light by mixing with a small amount and may be a metal complex such as a metal complex that emits light by multiple excitation that excites the triplet state.
- the dopant may be, for example, an inorganic, organic, or organic compound, and may include one or more species.
- Examples of the phosphorescent dopant include organic metal compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd,
- organic metal compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd,
- compounds represented by the following formulas can be used, but are not limited thereto. _
- M is a silver chelate
- X is the same or different from each other and is a ligand that forms a complex with M.
- X may be, for example, a bidentate ligand. More specifically,
- the phosphorescent dopant may be an organometallic compound represented by the following chemical formula (1) .
- II is selected from among, II, III, IV and IV;
- X to O04 are, independently of each other, nitrogen or carbon;
- 01 and 02 ring may be, independently of one another, substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted fluoren, substituted or unsubstituted spiro-fluorene, substituted or unsubstituted indene, Substituted or unsubstituted pyrazole, substituted or unsubstituted thiazole, substituted or unsubstituted thiophene, substituted or unsubstituted thiazole, substituted or unsubstituted thiazole, substituted or unsubstituted thiazole, substituted or unsubstituted thiazole, substituted or unsubstituted thiazole, substituted or unsubstituted thiazole, Substi
- substituted benzooxazole substituted or unsubstituted isobenzoxazole, substituted or unsubstituted triazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted triazine, substituted or unsubstituted dibenzo furan 3 ⁇ 4 6 0 ⁇ 3 ⁇ 411) and a substituted or unsubstituted dibenzothiophene is selected from thiophene ring; where "substituted” means that at least one hydrogen in the substituent or compound deuterium, a halogen group, a hydroxyl group a cyano group, an amino group, a substituted Or unsubstituted A substituted or unsubstituted C1 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstit
- a cycloalkyl group Means a cycloalkyl group, a cycloalkyl group having from 0 to 30 carbon atoms, a heterocyclic cycloalkyl group having from 0 to 30 carbon atoms, an aryl group having from 0 to 30 carbon atoms, a heterocyclic group having from 0 to 30 carbon atoms, a (1-20) alkoxy group, a ⁇ 31 to 010 trifluoroalkyl group, ; Is an organic ligand; Is 1, 2 or 3; to be.
- the above may be any monovalent, divalent or trivalent organic ligand.
- 101 may be a halogen ligand (e.g., a 3 ⁇ 4 diketone ligand (eg,
- carboxylic acid ligands for example, picolinate, dimethyl-3-pyrazole-carboxylic silryeyi agent, benzoate
- carbon monoxide ligand isonitrile ligand
- cyano ligand and phosphorus ligand e.g., phosphine (I), Phosphite ()
- a linking group for example, O alkyl group, -11 '
- the phosphorescent dopant may be a red or green phosphorescent dopant, and may be selected from, but not limited to, the following compounds:
- the mobility of the charge can be controlled by controlling the ratio of the compound for the second organic optoelectronic device and the compound for the first organic optoelectronic device.
- the combination ratio of the dopant The compound for a first organic optoelectronic device and the compound for a second organic optoelectronic device may be contained at a weight ratio of, for example, 1:10 to 10: 1. In particular, it may be 2: 8 to 8: 2, 9: 1 to 5: 5, 8: 2 to 5: 5, The mixing weight ratio of compound for optoelectronic device can be 5: 5.
- the composition may be formed by a dry film forming method such as chemical vapor deposition or a solution process.
- the organic optoelectronic device includes an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, and the organic layer may include the composition for the organic optoelectronic device described above.
- the organic layer includes a light emitting layer
- the light emitting layer may include the composition for an organic optoelectronic device of the present invention. 2019/132399 1 »(: 1 ⁇ ⁇ 2018/016246
- composition for the organic optoelectronic device may be included as a host of the light emitting layer, for example, as a green host.
- the organic layer may include at least one auxiliary layer selected from a light emitting layer and a hole injecting layer, a hole transporting layer, an electron blocking layer, an electron transporting layer, an electron injecting layer and a hole blocking layer, .
- the organic optoelectronic device is not particularly limited as long as it is a device capable of converting electric energy and optical energy.
- Examples of the organic optoelectronic device include organic light emitting devices, organic solar cells, and organic photoconductor drums.
- an organic light emitting diode 100 according to an exemplary embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 positioned between the anode 120 and the cathode 110, .
- the anode 120 may be made, for example, of a high work function conductive body to facilitate hole injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer.
- the anode 120 may be made of a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; zinc oxide, indium oxide, indium tin oxide (0)
- metal oxides such as zinc oxide indum ( ⁇ 0) poly (3-methyl thiophene), poly (3, 4- (ethylene-1, 2- Conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.
- the cathode 110 may be made of a conductive material having a low work function, for example, to facilitate electron injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer.
- the cathode 110 is made of a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lyrium, gadolinium, aluminum, silver, tin, lead, cesium, barium or the like or an alloy thereof; Materials, but are not limited thereto.
- the organic layer 105 includes the light emitting layer 130 including the compound for the organic optoelectronic device described above. 2019/132399 1 »(: 1 ⁇ ⁇ 2018/016246
- FIG. 40 is a sectional view showing an organic light emitting device according to another embodiment.
- the organic light emitting diode 200 further includes a hole-assist layer 140 in addition to the light-emitting layer 130.
- the hole assist layer 140 can further enhance hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.
- the hole-assist layer 140 may be, for example, a hole transport layer, a hole injection layer, and / or an electron blocking layer, and may include at least one layer.
- the organic layer 105 of FIG. 1 or 2 may include an additional layer of an electron injecting layer, an electron transporting layer, an electron transporting auxiliary layer, a hole transporting layer, a hole transporting auxiliary layer, a hole injecting layer, or a combination layer thereof.
- the organic light emitting devices 100 and 200 may be formed by forming an anode or a cathode on a substrate and then performing a vacuum evaporation process, A wet film formation method such as a spin coating method, a dipping method and a flow coating method is used to form an organic layer and then a cathode or anode is formed thereon Can be manufactured.
- the organic light emitting device described above can be applied to an organic light emitting display.
- Synthesis Example 1 Synthesis of Compound 2 2019/132399 1 »(: 1/10 ⁇ 018/016246
- reaction mixture was cooled to room temperature, and THF and distilled water were separated, and then separated THF was added dropwise to 100 mL of methanol to crystallize the resulting solid, which was then filtered and washed with water and methanol. The resulting solid was dried in a vacuum oven to give compound 3-A (20 g, 76% yield).
- the reaction product was poured into methanol to filtrate the solid, and the resulting solid was thoroughly washed with water and methanol and dried, and the resultant was dissolved in 500 mL of chlorobenzene , And the solution was then subjected to silica gel filtration and the solvent was completely removed. The solution was dissolved in 400 mL of toluene by heating and then recrystallized to obtain 16.54 g (yield 69%) of the compound C-99.
- the glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 A was washed with distilled water ultrasonic wave. After washing with distilled water, it was ultrasonically cleaned with isopropyl alcohol, acetone, and methanol, dried and transferred to a plasma cleaner The substrate was cleaned using oxygen plasma for 10 minutes, and then the substrate was transferred to a vacuum co-evaporator.
- Compound A was vacuum deposited on the ITO substrate using the ITO transparent electrode thus prepared to form a hole injection layer having a thickness of 700 A
- Compound B was deposited to a thickness of 50 A on the injection layer, and Compound C was deposited to a thickness of 1020 A to form a hole transport layer.
- Compound C-99 and Compound 2 were simultaneously used as a host on the hole transport layer, Ir (ppy) 3 by the Ping also 7wt% in a vacuum vapor deposition to form an emission increase of 400 a thickness, where the compound C-99 and compound 2 is 6: 4 weight ratio to the embodiment was used to, for example, Compound D and Liq were simultaneously vacuum deposited on the light emitting layer at a ratio of 1: 1 to form an electron transport layer having a thickness of 300 A. Liq l5A and Al 1200 A were successively vacuum-deposited on the electron transport layer Thereby forming an organic light emitting device.
- the organic light emitting device has a structure having five organic thin film layers. Specifically, the organic light emitting device has the following structure.
- Example 2 2-yl) phenyl) quinolone.
- Example 3 and Comparative Example 1 < RTI ID 0.0 >
- Example 2 The organic light emitting devices of Example 2, Example 3, and Comparative Example 1 were fabricated in the same manner as in Example 1. evaluation
- a current-voltmeter (1 ⁇ 6 2400) and 15, 111 by measuring the drive voltage of each element in the show / 0 and 2 results were obtained using a.
- the voltage The current value flowing through the unit device was measured using a current-voltmeter (1 ⁇ ⁇ oil! 6 2400) while increasing the current value to 10 ⁇ and the measured current value was divided by the area to obtain the result.
- the voltage was increased from 0 to 10 ⁇
- the luminance at that time was measured by using the luminance meter (0 ⁇ 03-1000 hr), and the result was obtained.
Abstract
화학식 1로 표현되는 유기 광전자 소자용 화합물; 이를 포함하는 유기 광전자 소자용 조성물, 이를 적용한 유기 광전자 소자 및 표시 장치에 관한 것이다. 상기 화학식 1에 대한 상세 내용은 명세서에서 정의한 바와 같다.
Description
2019/132399 1»（：1^1{2018/016246
【명세서】
【발명의 명칭】
유기광전자소자용화합물，유기 광전자소자용조성물,유기광전자소자 및표시 장치
【기술분야】
유기 광전자소자용화합물，유기 광전자소자용조성물,유기 광전자소자 및표시 장치에 관한것이다.
【배경기술】
유기광전자소자 (orgmic optoelectronic diode)는전기 에너지와광에너지를 상호전환할수있는소자이다.
유기 광전자소자는동작원리에따라크게두가지로나눌수있다. 하나는 광에너지에의해형성된엑시톤 (exdton)이 전자와정공으로분리되고상기 전자와 정공이각각다른전극으로전달되면서 전기 에너지를발생하는광전소자이고, 다른하나는전극에 전압또는전류를공급하여 전기 에너지로부터광에너지를 발생하는발광소자이다.
유기 광전자소자의 예로는유기 광전소자·,유기발광소자,유기 태양전지 및유기 감광체드럼 (organic photo conductor drum)등을들수있다.
이중,유기 발광소자 (organic light emitting diode, OLED)는근래평판표시 장치 (flat panel display device)의수요증가에 따라크게주목받고있다. 상기유기 발광소자는유기발광재료에 전류를가하여 전기 에너지를빛으로전환시키는 소자로서，통상양극 (anode)과음극 (cathode)사이에유기증이삽입된구조로 이루어져 있다. 여기서유기층은발광층과선택적으로보조층을포함할수있으며， 상기보조층은예컨대유기발광소자의 효율과안정성을높이기위한정공주입층， 정공수송층，전자차단층，전자수송층，전자주입 층및정공차단층에서 선택된적어도 1층을포함할수있다.
유기발광소자의성능은상기유기층의특성에 의해영향을많이 받으며， 그중에서도상기유기층에포함된유기 재료에의해영향을많이 받는다.
특히상기유기발광소자가대형 평판표시 장치에 적용되기위해서는정공 및전자의 이동성을높이는동시에 전기화학적 안정성을높일수있는유기 재료의 개발이 필요하다.
2019/132399 1»（：1^1{2018/016246
2
【발명의상세한설명】
【기술적과제】
일구현예는고효율및장수명유기 광전자소자를구현할수있는유기 광전자소자용화합물을제공한다.
다른구현예는상기조성물을포함하는유기 광전자소자용조성물을 제공한다.
또다른구현예는상기유기광전자소자용조성물을포함하는유기 광전자 소자및표시 장치를제공한다.
【기술적해결방법】
일구현예에따르면,하기 화학식 1로표현되는유기 광전자소자용화합물을 제공한다.
[화학식 1]
상기화학식 1에서，
X1은 0또는요이고，
내지 II8은각각독립적으로수소，중수소,시아노기，치환또는비치환된 （그1내지 010알킬기,치환또는비치환된 06내지 020아릴기,또는치환또는 비치환된 02내지 030헤테로고리기이고,
상가 II6및 II7중적어도하나는 1개이상의 질소원자를포함하는치환 또는비치환된 02내지 030헤테로고리기이고，
상기묘5내지묘8중적어도하나는하기화학식 2로표현되고,
[화학식 2]
3 상기화학식 2에서,
X2는 0또는 이고,
^내지 3은각각독립적으로수소，중수소,시아노기，치환또는비치환된 0\내지 010알킬기,치환또는비치환된€6내지 020아릴기,또는치환또는 비치환된 02내지 030헤테로고리기이다.
다른구현예에따르면，상기유기 광전자소자용화합물을포함하는유기 광전자소자용조성물을제공한다.
또다른 .구현예에따르면,서로마주하는양극과음극，그리고상기 양극과 상기음극사이에 위치하는적어도한층의유기층을포함하고，상기유기층은 전술한유기광전자소자용화합물또는유기 광전자소자용조성물을포함하는 유기광전자소자를제공한다.
또다른구현예에따르면상기유기광전자소자를포함하는표시 장치를 제공한다.
【발명의효과】
고효율장수명유기광전자소자를구현할수있다.
【도면의 간단한설명】
도 1및도 2는일구현예에 따른유기 발광소자를도시한단면도이다.
＜부호의설명
100, 200:유기 발광소자
105:유기층
110:음극
120:양극
130:발광층
140:정공보조증
【발명의실시를위한최선의 형태】
이하，본발명의구현예를상세히설명하기로한다. 다만，이는예시로서 제시되는것으로,이에의해본발명이 제한되지는않으며 본발명은후술할 청구범위의 범주에 의해정의될뿐이다.
본명세서에서 "치환”이란별도의 정의가없는한,치환기또는화합물중의 적어도하나의수소가중수소，할로겐기,히드록실기，아미노기,치환또는비치환된
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4 이내지 30아민기，니트로기,치환또는비치환된 01내지 040실릴기,
030알킬기，（그1내지 010알킬실릴기, 06내지。30아릴실릴기, 03내지 030 시클로알킬기, 03내지 030헤테로시클로알킬기, 06내지 030아릴기, 02내지 030 헤테로아릴기,
내지 020알콕시기,（:1내지（：10트리플루오로알킬기,시아노기, 또는이들의조합으로치환된것을의미한다.
본발명의일예에서，”치환”은치환기또는화합물중의 적어도하나의 수소가중수소，
내지 030알킬기，（：1내지（：10알킬실릴기， 06내지 030 아릴실릴기, 03내지 030시클로알킬기，〔3내지 030헤테로시클로알킬기, 06내지 030아릴기, 02내지 030헤테로아릴기로치환된것을의미한다. 또한,본발명의 구체적인일 예에서，”치환”은치환기또는화합물중의 적어도하나의수소가 중수소,
알킬기， 06내지 030아릴기 ,또는 02내지 030
헤테로아릴기로치환된것을의미한다.또한，본발명의 구체적인일 예에서,
"치환"은치환기또는화합물중의 적어도하나의수소가중수소,（：1내지 05 알킬기, 06내지 018아 1기,디벤조퓨란일기,또는디벤조티오펜일기로치환된것을 의미한다.또한，본발명의구체적인일예에서,”치환”은치환기또는화합물중의 적어도하나의수소가중수소，메틸기，에틸기,프로판일기,부틸기，페닐기， 바이페닐기，터페닐기，나프틸기，트리페닐기，플루오레닐기，디벤조퓨란일기또는 디벤조티오펜일기로치환된것을의미한다.
본명세서에서 "헤테로"란별도의 정의가없는한，하나의작용기내에代0, 및 ¾로이루어진군에서선택되는헤테로원자를 1내지 3개함유하고， 나머지는탄소인것을의미한다.
본명세서에서’’알킬（ 1어）기"이란별도의 정의가없는한，지방족
탄화수소기를의미한다. 알킬기는어떠한아중결합이나삼중결합을포함하고있지 않은 "포화알킬作 선 ¾;；71）기 "일수있다.
상기 알킬기는＜그1내지 030인알킬기일수있다. 보다구체적으로알킬기는
01내지 020알킬기또는＜그1내지 010알칼기일수도있다.
C4알킬기는알킬쇄에 1내지 4개의 탄소원자가포함되는것을의미하며，메틸， 에틸，프로필，이소-프로필 , 11-부틸,이소-부틸， -부틸및 부뭘로이루어진군에서 선택됨을나타낸다.
상기 알킬기는구체적인예를들어 메틸기，에틸기,프로필기，이소프로필기，
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5 부틸기,이소부틸기， t-부틸기，펜틸기，핵실기,시클로프로필기,시클로부틸기, 시클로펜틸기,시클로핵실기등을의미한다.
본명세서에서’’아릴 (aryl)기’’는탄화수소방향족모이어티를하나이상갖는 그룹을총괄하는개념으로서，
탄화수소방향족모이어티의모든원소가 p-오비탈을가지면서，이들 p- 오비탈이공액 (conjugation)을형성하고있는형태,예컨대페닐기，나프틸기등을 포함하고，
2이상의 탄화수소방향족모이어티들이시그마결합을통하여 연결된형태， 예컨대바이페닐기，터페닐기,쿼터페닐기등을포함하며，
2이상의탄화수소방향족모이어티들이 직접또는간접적으로융합된 비방향족융합고리도포함할수있다. 예컨대,플루오레닐기등을들수있다. 아릴기는모노시클릭,폴리시클릭또는융합고리폴리시클릭 (즉，
탄소원자들의 인접한쌍들을나눠가지는고리)작용기를포함한다.
본명세서에서 "헤테로고리기 (heterocyclic group)”는헤테로아릴기를포함하는 상위개념으로서,아릴기,시클로알킬기，이들의융합고리또는이들의조합과같은 고리화합물내에 탄소 (C)대신 N, O, S, P및 Si로이루어진군에서선택되는 헤테로원자를적어도한개를함유하는것을의미한다.상기헤테로고리기가 융합고리인경우,상기헤테로고리기 전체또는각각의고리마다헤테로원자를한 개이상포함할수있다.
일예로 "헤테로아릴 (heteroaryl)기”는아릴기 내에 N, O, S, P및 Si로이루어진 군에서선택되는헤테로원자를적어도한개를함유하는것을의미한다 .2이상의 헤테로아릴기는시그마결합을통하여 직접 연결되거나，상기헤테로아릴기가 2 이상의고리를포함할경우， 2이상의 고리들은서로융합될수있다. 상기
헤테로아릴기가융합고리인경우,각각의고리마다상기 헤테로원자를 1내지 3개 포함할수있다.
보다구체적으로,치환또는비치환된 C6내지 C30아릴기는,치환또는 비치환된페닐기，치환또는비치환된나프틸기,치환또는비치환된안트라세닐기, 치환또는비치환된페난트레닐기，치환또는비치환된나프타세닐기，치환또는 비치환된피레닐기,치환또는비치환된바이페닐기，치환또는비치환된 p-터페닐기， 치환또는비치환된 m-터페닐기，치환또는비치환된 0-터페닐기，치환또는
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6 비치환된크리세닐기,치환또는비치환된트리페닐렌기,치환또는비치환된 페릴레닐기,치환또는비치환된플루오레닐기,치환또는비치환된인데닐기,또는 이들의조합일수있으나,이에 제한되지는않는다.
보다구체적으로,치환또는비치환된 C2내지 C30헤테로고리기는,치환 또는비치환된퓨라닐기，치환또는비치환된티오페닐기,치환또는비치환된 피롤릴기,치환또는비치환된피라졸릴기，치환또는비치환된이미다졸일기,치환 또는비치환된트리아졸일기，치환또는비치환된옥사졸일기,치환또는비치환된 티아졸일기，치환또는비치환된옥사디아졸일기,치환또는비치환된
티아디아졸일기,치환또는비치환된피리딜기,치환또는비치환된피리미디닐기, 치환또는비치환된피라지닐기,치환또는비치환된트리아지닐기,치환또는 비치환된벤조퓨라닐기，치환또는비치환된벤조티오페닐기,치환또는비치환된 벤즈이미다졸일기,치환또는비치환된인돌일기,치환또는비치환된퀴놀리닐기， 치환또는비치환돤이소퀴놀리닐기,치환또는비치환된퀴나졸리닐기,치환또는 비치환된퀴녹살리닐기,치환또는비치환된벤조퀴놀리닐기，치환또는비치환된 벤조이소퀴놀리닐기，치환또는비치환된벤조퀴나졸리닐기，치환또는비치환된 나프티리디닐기,치환또는비치환된벤즈옥사진일기,치환또는비치환된
벤즈티아진일기,치환또는비치환된아크리디닐기,치환또는비치환된페나진일기, 치환또는비치환된페노티아진일기,치환또는비치환된페녹사진일기,치환또는 비치환된디벤조퓨란일기,또는치환또는비치환된디벤조티오펜일기，또는이들의 조합일수있으나,이에 제한되지는않는다.
본명세서에서，정공특성이란，전기장 (electric field)을가했을때전자를 공여하여 정공을형성할수있는특성을말하는것으로， HOMO준위를따라전도 특성을가져 양극에서 형성된정공의 발광층으로의주입,발광층에서 형성된정공의 양극으로의 이동및발광층에서의 이동을용이하게하는특성을의미한다.
또한전자특성이란，전기장을가했을때전자를받을수있는특성을말하는 것으로, LUMO준위를따라전도특성을가져음극에서 형성된전자의 발광층으로의 주입，발광층에서 형성된전자의음극으로의 이동및발광층에서의 이동을용이하게 하는특성을의미한다. 이하일구현예에따른유기 광전자소자용조성물을설명한다.
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7 일구현예에따른유기 광전자소자용화합물은하기화학식 1로표현될수 있다.
[화학식 1]
상기화학식 1에서,
X1은 0또는 이고，
내지 II8은각각독립적으로수소，중수소，시아노기,치환또는비치환된 01내지 010알킬기,치환또는비치환된 06내지 020아릴기,또는치환또는 비치환된 02내지 030헤테로고리기이고,
상기 및묘7중적어도하나는 1개 이상의 질소원자를포함하는치환 또는비치환된 02내지 030헤테로고리기이고,
상기 내지모8중적어도하나는하기화학식 2로표현되고，
[화학식 2]
상기화학식 2에서，
는 0또는요이고,
묘9내지모13은각각독립적으로수소,중수소,시아노기,치환또는비치환된 01내지 010알킬기,치환또는비치환된 06내지 020아릴기，또는치환또는 비치환된 02내지 030헤테로고리기이다.
상기화학식 1로표현되는화합물은유기광전자소자에서 전자주입， 전자수송또는발광물질의 역할을할수있으며，특히 발광물질로사용될경우 구동전압을저하시킴과동시에교효율의유기광전자소자를제작할수있다. 상기화학식 1에서，상기 내지 II8중적어도하나는하기화학식 2로
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8 표현되기 때문에극성기를가지게되고,이로인해전극과의상호작용이가능해져 전자의주입이용이하고이동도가높아지게되며，궁극적으로구동전압저하및 고효율효과를동시에 얻을수있다.또한,상기 화학식 1로표현되는화합물은 비대칭구조를가지는바,증착시의분해를억제할수있다.
본발명의 일실시예에서,상기화학식 1에서，상기묘6및 7중적어도 하나는치환또는비치환된피리디닐기,치환또는비치환된피리미디닐기,치환 또는비치환된트리아지닐기，치환또는비치환된퀴나졸리닐기또는치환또는 비치환된벤조티에노피리미디닐기일수있다.
예컨대,상기묘6및 II7중적어도하나는하기 화학식 3으로표현될수있다. [화학식 3]
015
상기화학식 3에서,
X3내지 X5는각각독립적으로 또는 0^（^^수소또는（：1내지 010 알킬기임）이고，
X3내지 X5중적어도하나이상은 이고，
요14및 5는각각독립적으로수소,중수소，시아노기，치환또는비치환된 01내지 010알킬기,치환또는비치환된 06내지 020아릴기,또는치환또는 비치환된 02내지 030헤테로고리기이다.
상기화학식 3에서,상기 X3내지 X5중적어도둘이상은 일수있다. : 상기화학식 3에서，상기모14및 5는각각독립적으로하기그룹 I에서 선택된어느하나의 치환기일수있다.
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9
[그룹 I]
상기화학식 2는하기화학식 2-1또는화학식 2-2로표현될수있다.
[화학식 2-1] [화학식 2-2]
상기화학식 2-1내지화학식 2-2에서，
X2는각각독립적으로 0또는 이고，
묘9내지 II13은각각독립적으로수소，중수소，시아노기,치환또는비치환된 01내지 010알킬기，치환또는비치환된 06내지 020아릴기,또는치환또는 비치환된 02내지 030헤테로고리기이다.
예컨대,상기 화학식 1로표현되는유기광전자소자용화합물은하기 그룹 1에 나열된화합물에서선택될수있으나，이에 한정되는것은아니다.
[그룹 1]
15
전술한유기광전자소자용화합물은단독으로또는다른유기 광전자 소자용화합물과함께유기 광전자소자에 적용될수있다. 전술한유기 광전자 소자용화합물이단독으로또는다른유기 광전자소자용화합물과함께사용되는 경우，조성물의 형태로적용될수있다.
본발명은상기에서 언급한상기화학식 1로표현되는유기광전자소자용 화합물（제 1유기광전자소자용화합물）을포함하는유기광전자소자용조성물을 제공한다.
또한，본발명은상기 제 1유기 광전자소자용화합물및하기의화학식 4로 표현되는화합물（제 2유기 광전자소자용화합물）을포함하는유기전자소자용 조성물을제공할수있다.
[화학식 4]
상기화학식 4에서,
및 는각각독립적으로단일결합,치환또는비치환된 06내지 030 아릴렌기，치환또는비치환된 02내지 030헤테로아릴렌기，또는이들의조합이고，
1및사2는각각독립적으로치환또는비치환된 06내지 030아릴기，치환
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111은 0내지 2의정수중하나이다.
본발명의 일실시예에서，상기화학식 4의 V1및 는각각독립적으로 단일결합，또는치환또는비치환된 06내지 018아릴렌기일수있다.
본발명의 일실시예에서,상기화학식 4의쇼 및쇼는각각독립적으로, 치환또는비치환된페닐기，치환또는비치환된바이페닐기,치환또는비치환된 터페닐기，치환또는비치환된나프틸기,치환또는비치환된안트라세닐기,치환 또는비치환된트리페닐레닐기,치환또는비치환된피리디닐기,치환또는 비치환된피리미디닐기,치환또는비치환된퀴나졸일기,치환또는비치환된 이소퀴나졸일기，치환또는비치환된디벤조티오펜일기，치환또는비치환된 디벤조퓨란일기，치환또는비치환된카바졸일기，치환또는비치환된플루오레닐기, 또는이들의조합일수있다.
본발명의 일실시예에서，상기화학식 4의 6내지 1은각각독립적으로 수소,중수소,또는치환또는비치환된 06내지（：12아릴기일수있다.
본발명의 일실시예에서,상기화학식 4의 111은 0또는 1일수있다.
본발명의구체적인일실시예에서,상기 화학식 4는하기그룹 II에나열된 구조중하나이고,
江［에 나열된치환기중 하나일수있다.
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[그룹 五 ]
상기그룹 II 및그룹 III에서，*은연결지점이다.
구체적으로,상기화학식 4는상기 그룹 II의 0-8로표현되고，상기
및 *- - 2는상기그룹 III의 6-1내지 4중어느하나로표현될수있다. 더욱구체적으로，상기
이들의조합에서선택될수있다.
상기화학식 4로표시되는제 2유기광전자소자용화합물은예컨대하기
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18 그룹 2에나열된화합물일수있으나,이에 한정되는것은아니다·
[그룹 2]
10
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또한， 본 발명은 상기 제 1 유기 광전자소자용 화합물 및 하기 화학식 5로 표현되는 모이어티와하기 화학식 6으로표현되는모이어티의 조합으로 이루어진 화합물（제 2 유기 광전자소자용화합물）을포함하는유기 광전자소자용 조성물을
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23 제공할수있다.
[화학식 5] [화학식 6]
상기화학식 5및화학식 6에서，
' 및 4는각각독립적으로단일결합，치환또는비치환된 06내지 30 아릴텐기，치환또는비치환된 02내지 030헤테로아릴렌기，또는어들의조합이고, 쇼1_3및 4는각각독립적으)-·一—로치환또는비치환된 06내지 030아릴기,치환 또는비치환된 02내지 030헤테로고리기，또는이들의조합이고，
2내지 II25는각각독립적으로수소,중수소,치환또는비치환된 01내지 020알킬기,치환또는비치환된 06내지 050아릴기,치환또는비치환된 02내지
050헤테로고리기또는이들의조합이고，
상기화학식 5의 인접한두개의 *는상기화학식 6의두개의 *와결합하여 융합고리를형성하고，상기화학식 5에서융합고리를형성하지 않은 *는각각 독립적으로 ^이고，
수소,중수소,치환또는비치환된（그1내지 010알킬기,치환또는 비치환된 06내지（：12아릴기，치환또는비치환된 01내지 012헤테로고리기， 또는이들의조합이다.
예컨대，상기쇼#및쇼/는각각독립적으로,치환또는비치환된페닐기， 치환또는비치환된바이페닐기,치환또는비치환된터페닐기,또는이들의조합일 수있다.
예컨대,상기 3및쇼/중적어도하나는치환또는비치환된카바졸기를 포함할수있다.
상기화학식 5로표현되는모이어티와상기화학식 6으로표현되는
모이어티의조합으로이루어진제 2유기화합물은결합위치에 따라예컨대하기 화학식 7-1내지 7-5중어느하나로표현될수있다.
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[화학식 7-1] [화학식 7-2]
상기화학식 7-1내지 7-5에서,
및 는각각독립적으로단일결합，치환또는비치환된 06내지 030 아릴렌기，치환또는비치환된 02내지 030헤테로아릴렌기또는이들의조합이고, 사3및 4는각각독립적으로치환또는비치환된 06내지 030아릴기，치환 또는비치환된 02내지 030헤테로고리기또는이들의조합이고,
2내지 5는각각독립적으로수소,중수소，치환또는비치환된 01내지 020알킬기,치환또는비치환된 06내지 050아릴기，치환또는비치환된 C2내지 50헤테로고리기또는이들의조합이다.
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25 예컨대,상기 화학식 7-1내지 7-5의 3및 4중적어도하나는정공 특성을가지는치환기일수있으며，예컨대，치환또는비치환된카바졸기를포함할 수있다. 상기 화학식 5로표현되는모이어티와상기 화학식 6으로표현되는 모이어티의 조합으로이루어진제 2유기 광전자소자용화합물은예컨대하기 그룹 II에 나열된화합물일수있으나，이에 한정되는것은아니다.［그룹 IV］（하기 ［그룹 IV］에 기재된구체화합물에서，헤테로원자는
이다.）
［그룹 IV］
대체용지（규직제 26조）
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대체용지（규직제26조）
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일실시예에 따른조성물은유기 광전자소자의유기층에 적용될수있으며, 예컨대유기 광전자소자의 발광층에 적용될수있으며，상기 제 1유기 광전자 소자용화합물과상기 제 2유기 광전자소자용화합물은호스트（ ）로서 역할을할 수있다. 이때,상기 제 1유기광전자소자용화합물은전자특성이상대적으로 강한바이폴라특성을가지는화합물일수있고상기 제 2유기 광전자소자용 화합물은정공특성이상대적으로강한바이폴라특성을가지는화합물로,상기 제 1 유기광전자소자용화합물과함께사용되어 전하의 이동성 및안정성을
높임으로써 발광효율및수명특성을더욱개선시킬수있다. ,
전자혹은정공특성이 한쪽으로치우친재료를발광층으로도입한소자는 발광층과전자또는정공수송층의 계면에서 캐리어의 재결합이 일어나면서 엑시톤의 형성이상대적으로많이 일어나게된다. 그결과발광층내분자 여기자와수송층계면의 전하와의상호작용으로인해효율이 급격히 떨어지는롤- 오프江011-（：0현상이 발생하고발광수명특성또한급격히떨어지게된다. 이러한 문제를해결하기위하여상기제 1유기 광전자소자용화합물및제 2유기 광전자 소자용화합물을호스트화합물로서동시에 발광층에도입하여 전자또는
정공수송층어느한쪽으로발광영역이 치우치지 않도록발광층내의 캐리어
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29 밸런스를맞출수있는소자를제작함으로써롤-오프의 개선과동시에 수명특성 또한현저히 개선시킬수있다.
전술한제 1유기광전자소자용화합물과제 2유기 광전자소자용화합물은 다양한조합에의해다양한조성물을준비할수있다.
전술한바와같이,상기 제 2유기 광전자소자용화합물은상기 제 1유기 광전자소자용화합물과함께발광층에사용되어 잔하의 이동성을높이고안정성을 높임으로써구동전압，발광효율및수명특성을개선시킬수있다.
또한,상기 제 1유기 광전자소자용화합물과제 2유기 광전자소자용 화합물은예컨대 약 1:9내지 9:1, 2:8내지 8:2, 3:7내지 7:3, 4:6내지 6:4,그리고 5:5의중량비로포함될수있고,구체적으로 1:9내지 8:2, 1:9내지 7:3, 1:9내지 6:4,
1:9내지 5:5의중량비로포함될수있으며,더욱구체적으로， 2:8내지 7:3, 2:8내지 6:4,그리고 2:8내지 5:5의중량비로포함될수있다. 또한， 3:7내지 6:4,그리고 3:7 내지 5:5의중량비로포함될수있으며,가장구체적으로 3:7내지 4:6또는 5:5의 중량비로포함될수있다.
상기유기광전자소자용조성물은그린또는레드유기발광소자의호스트로 사용될수있다.
상기유기광전자소자용화합물또는조성물은다른유기광전자소자용 화합물외에 1종이상의유기화합물을더포함할수있다.
상기제 1유기광전자소자용화합물과제 2유기 광전자소자용화합물을 포함하는조성물은도판트를더포함할수있다.
상기도펀트는적색,녹색또는청색의도펀트일수있으며,예컨대적색 또는녹색의 인광도펀트일수있다.
상기도펀트는미량혼합되어 발광을일으키는물질로，일반적으로삼중항 상태이상으로여기시키는다중항여기 (multiple excitation)에 의해발광하는금속 착체 (metal complex)와같은물질이사용될수있다. 상기 도펀트는예컨대무기， 유기，유무기화합물일수있으며， 1종또는 2종이상포함될수있다.
상기 인광도펀트의 예로는 Ir，Pt, Os, Ti, Zr，Hf，Eu，Tb，Tm，Fe，Co，Ni, Ru，Rh, Pd 또는이들의조합을포함하는유기금속화합물을들수있고,예컨대하기화학식 로표현되는화합물을사용할수있으나，이에 한정되는것은아니다. _
[화학식 Z]
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1>21ᆻ故
상기화학식 에서， M은금속이고, 및 X는서로같거나다르며 M과 착화합물을형성하는리간드이다.
이들의조합일수있고，상기 및 X는예컨대바이덴테이트리간드일수있다. 더욱구체적으로,상기
1切, 1¾，? 1또는이들의조합중하나를포함하는유기금속화합물일수있고, 구체적인밀실시예에서,상기 인광도펀트는하기화학식 4()1로표시되는 유기금속화합물일수있다.
<화학식 401 ñ
상기 화학식 401중， 은 II·， ,이, ¾ ¾ ¾ ¾ ¾및 ¾중에서선택되고; X 내지 ¾04는서로독립적으로，질소또는탄소이고; 01및 02고리는서로 독립적으로,치환또는비치환된벤젠,치환또는비치환된나프탈렌，치환또는 비치환된플루오텐，치환또는비치환된스파이로-플루오렌，치환또는비치환된 인덴，치환또는비치환된피롤,치환또는비치환된티오펜，치환또는비치환된 퓨란 ( )，치환또는비치환된이미다졸,치환또는비치환된피라졸，치환또는 비치환된티아졸,치환또는비치환된이소티아졸，치환또는비치환된옥사졸，치환 또는비치환된이속사졸 예 크 뗘,치환또는비치환된피리딘,치환또는비치환된 피라진，치환또는비치환된피리미딘,치환또는비치환된피리다진,치환또는 비치환된퀴놀린,치환또는비치환된이소퀴놀린，치환또는비치환된벤조퀴놀린, 치환또는비치환된퀴녹살린,치환또는비치환된퀴나졸린，치환또는비치환된 카바졸,치환또는비치환된벤조이미다졸,치환또는비치환된벤조퓨란
치환또는비치환된벤조티오펜,치환또는비치환된이소벤조티오펜,치환또는
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31 비치환된벤조옥사졸，치환또는비치환된이소벤조옥사졸,치환또는비치환된 트리아졸，치환또는비치환된옥사디아졸,치환또는비치환된트리아진，치환또는 비치환된디벤조퓨란 ¾6 0加¾11）및치환또는비치환된디벤조티오펜중에서 선택되고;여기서 "치환”이란치환기또는화합물중의 적어도하나의수소가 중수소,할로겐기,히드록실기 시아노기,아미노기,치환또는비치환된
내지 030아민기，니트로기，치환또는비치환된 01내지。40실릴기， 01내지 030 알킬기,（〕1내지 010알킬실릴기， 06내지 030아릴실릴기, 03내지 030
시클로알킬기, 03내지 030헤테로시클로알킬기, 06내지 030아릴기, 02내지 030 헤테로고리기，（：1내지 020알콕시기，＜31내지 010트리플루오로알킬기,또는이들의 조합으로치환된것을의미하고; 이은유기 리간드이고;
은 1, 2또는 3이고;
이다.
상기 이은임의의 1가， 2가또는 3가의유기 리간드일수있다.예를들어, 1 01은할로겐리간드（예를들면, ，¾디케톤리간드（예를들면，
아세틸아세토네이트, 1,3 -디페닐- 1，3 -프로판디오네이트, 2,2,6,6 -테트라메틸- 3,5- 헵탄디오네이트,핵사플루오로아세토네이트），카르복실산리간드（예를들면, 피콜리네이트,디메틸- 3 -피라졸카르복실례이트，벤조에이트）,카본모노옥사이드 리간드，이소니트릴리간드,시아노리간드및포스포러스리간드（예를들면， 포스핀（ 야 ）,포스파이트（ 야 ））중선택될수있으나,이에 한정되는것은 아니다.
상기화학식 401
치환기를가질경우, 이의 2이상의 치환기를서로결합하여포화또는불포화고리를형성할수있다.
상기화학식 401중쇼402가 2이상의치환기를가질경우, 02의 2아상의 치환기를서로결합하여포화또는불포화고리를형성할수있다.
상기화학식 401중 1이 2이상일경우,화학식 401중복수의 리간드
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예컨대,상기 인광도펀트는적색또는녹색의 인광도펀트일수있으며, 하기화합물 ?01내지 ?075중에서 선택될수있으나,이에 한정되는것은아니다:
905 ?06
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0
또한상기 제 2유기 광전자소자용화합물과상기 제 1유기 광전자소자용 화합물의 비율을조절함으로써 전하의 이동성을조절할수있다.본발명의 조성물이호스트로사용되는경우이들의조합비율은사용된도판트의종류나 도판트의성향에따라달라질수있으며,상기 제 1유기 광전자소자용화합물과 상기 제 2유기 광전자소자용화합물은예컨대 1:10내지 10:1의중량비로포함될 수있다. 구체적으로 2:8내지 8:2, 9:1내지 5:5， 8:2내지 5:5, 7:3내지 5:5일수 있고 가장구체적인예로서，제 1유기 광전자소자용화합물과제 2유기 광전자 소자용화합물의혼합중량비는 5:5일수있다.
상기중량비 범위로포함됨으로써 바이폴라특성이 더욱효과적으로 구현되어효율과수명을동시에 개선할수있다.
상기조성물은화학기상증착과같은건식성막법 또는용액공정으로형성될 수있다.
이하전술한유기 광전자소자용조성물을적용한유기 광전자소자를 설명한다.
다른구현예에 따른유기 광전자소자는서로마주하는양극과음극,그리고 상기 양극과상기음극사이에 위치하는적어도한층의유기층을포함하고，상기 유기층은전술한유기 광전자소자용조성물을포함할수있다.
일예로상기유기층은발광층을포함하고,상기 발광층은본발명의유기 광전자소자용조성물을포함할수있다.
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39 구체적으로,상기유기광전자소자용조성물은상기발광층의호스트， 예컨대그린호스트로서포함될수있다.
또한,상기유기층은발광층,및정공주입층，정공수송층,전자차단층， 전자수송층，전자주입층및정공차단층에서선택된적어도하나의보조층을 포함하고,상기보조층은상기유기광전자소자용조성물을포함할수있다.
상기유기광전자소자는전기에너지와광에너지를상호전환할수있는 소자이면특별히 한정되지 않으며,예컨대유기광전소자，유기발광소자,유기 태양전지 및유기 감광체드럼등을들수있다.
여기서는유기 광전자소자의 일 예인유기 발광소자를도면을참고하여 설명한다.
도 1및도 2는일구현예에 따른유기발광소자를보여주는단면도이다. 도 1을참고하면,일구현예에따른유기 발광소자 (100)는서로마주하는 양극 (120)과음극 (110)，그리고양극 (120)과음극 (110)사이에위치하는유기층 (105)을 포함한다.
양극 (120)은예컨대정공주입이 원활하도록일함수가높은도전체로 만들어질수있으며,예컨대금속,금속산화물및/또는도전성고분자로만들어질 수있다. 양극 (120)은예컨대니켈,백금,바나듐,크롬,구리,아연，금과같은금속 또는이들의합금;아연산화물，인듐산화물,인둠주석산화물 ( 0),
인둠아연산화물 (位0)과같은금속산화물;프110와 또는 ¾102와 와같은금속과 산화물의조합;폴리 (3 -메틸티오펜)，폴리 (3, 4-(에틸렌- 1,2-
폴리피롤및폴리아닐린과같은 도전성고분자등을들수있으나,이에 한정되는것은아니다.
음극 (110)은예컨대전자주입이 원활하도록일함수가낮은도전체로 만들어질수있으며,예컨대금속，금속산화물및/또는도전성고분자로만들어질 수있다. 음극 (110)은예컨대마그네슘,칼슘，나트륨，칼륨,타이타늄,인둠，이트륨, 리륨，가돌리늄，알루미늄，은,주석,납,세슘,바륨등과같은금속또는이들의 합금;
물질을들수 있으나,이에 한정되는것은아니다.
유기층 (105)은전술한유기 광전자소자용화합물을포함하는발광층 (130)을 포함한다.
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40 도 2는다른구현예에따른유기 발광소자를보여주는단면도이다.
도 2를참고하면，유기발광소자 (200)는발광층 (130)외에 정공보조층 (140)을 더포함한다. 정공보조층 (140)은양극 (120)과발광층 (130)사이의 정공주입 및/또는정공이동성을더욱높이고전자를차단할수있다. 정공보조층 (140)은 예컨대정공수송층,정공주입층및/또는전자차단층일수있으며,적어도 1층을 포함할수있다.
도 1또는도 2의유기층 (105)은도시하지는않았지만,전자주입층, 전자수송층,전자수송보조층,정공수송층,정공수송보조층，정공주입층또는이들의 조합층을추가로더포함할수있다. 본발명의유기광전자소자용화합물은이들 유기층에포함될수있다.유기 발광소자 (100, 200)는기판위에 양극또는음극을 형성한후，진공증착법 (evaporation),스퍼터링 (sputtering),들라즈마도금및 이온도금과같은건식성막법 ;또는스핀코팅 (spin coating),침지법 (dipping), 유동코팅법 (flow coating)과같은습식성막법등으로유기층을형성한후，그위에 음극또는양극을형성하여 제조할수있다.
전술한유기 발광소자는유기 발광표시장치에 적용될수있다.
【발명의 실시를위한형태】
이하에서는본발명의구체적인실시예들을제시한다. 다만,하기에 기재된 실시예들은본발명을구체적으로예시하거나설명하기 위한것에불과하며 ,이로서 본발명이 제한되어서는아니된다.
이하，실시예및합성예에서사용된출발물질및반응물질은특별한언급이 없는한, Sigma-Aldrich it또는 TCI It에서구입하였거나,공지된방법을통해 합성하였다.
(유기광전자소자용화합물의제조)
본발명와화합물의보다구체적인예로서 제시된화합물을하기 단계를 통해합성하였다.
(제 1유기광전자소자용화합물)
합성예 1 :화합물 2의합성
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(1)둥근바닥풀라스크에 4-bromo-2-chloro-Dibenzofuran 15 g (53.58 mmol), 2- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-Dibenzofurane 15.76 g (53.58 mmol),
테트라키스 (트리페닐포스핀)팔라듐 [Pd(PPh3)4] 1.858 g (1.61 mmol),포타슘카보네이트
7.406 g (53.58 mmol)을 THF 200 mL,증류수 100 mL에 넣고 12시간동안가열 환류하였다.반응이완결되면상온으로냉각하고 THF와증류수를분리한다음, 메탄올 100 mL에분리된 THF를적가하며 결정화시킨후,생성된고형물을여과하고, 물과메탄올로세정하였다.이로부터수득한고형물을진공오븐에서 건조하여 화합물 2-A (13 g, 66%와수율)을수득하였다.
MS(m/z, [M]+): 368.81
(2)둥근바닥플라스크에중간체화합물 2-A 13 g (35.32 mmol), Pd(dppf)C12 1.442 g (1.77 mmol), Tricyclohexylphosphine 1.981 g (7.06 mmol), Potassium Acetate 10.4 g (105.96 mmol), Bis(pinacolato)diboron 10.76 g (42.76 mmol)을 DMF lOO ml에현탁시키고 48시간 동안환류교반한다.반응종료후증류수 300 ml에 넣어 생성된고체를 1시간교반 하고 filter후,실리카겔필터하여목적화합물인화합물 2-B (10 g, 62°/c의수율)을 수득하였다.
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MS(m/z, [M]+): 460.33
(3)둥근바닥플라스크에 2-B 10 g (22.47 mmol), 2-chloro-4,6-diphenyl-l, 3,5- Triazine 6 g (22.47 mmol),테트라키스 (트리페닐포스핀)팔라듐 [Pd(PPh3)4] 1.298 g (1.12 mmol),포타슘카보네이트 9.315 g (67.4mmol)을 THF lOO mL,증류수 30 mL에 넣고 12시간동안가열환류하였다.반응이완결되면상온으로냉각하고 THF와증류수를 분리한다음,메탄올 lW mL에분리된 THF를적가하며 결정화시킨후,생성된 고형물을여과하고，물과메탄올로세정하였다.이로부터수득한고형물을 진공오븐에서건조하여 화합물 2 (9 g, 71%의수율)을수득하였다.
MS(m/z, [M]+): 565.62 합성예 2 :화합물 3의합성
[반응식]
43 환류하였다.반응이완결되면상온으로냉각하고 THF와증류수를분리한다음， 메탄올 100 mL에분리된 THF를적가하며 결정화시킨후,생성된고형물을여과하고, 물과메탄올로세정하였다.이로부터수득한고형물을진공오븐에서 건조하여 화합물 3-A (20 g，76%의수율)을수득하였다.
MS(m/z, [M]+): 368.81
(2)둥근바닥플라스크에중간체화합물 3-A 20 g (54.34 mmol), Pd(dppf)C122.2 g (2.72 mmol), Tricyclohexylphosphine 3 g (10.87 mmol), Potassium Acetate 16 g (163 mmol), Bis(pinacolato)diboron 16.55 g (65.21 mmol)을 DMF 135 ml에 현탁시키고 48시간동안 환류교반한다.반응종료후증류수 300 ml에 넣어 생성된고체를 1시간교반하고 filter후,실리카겔필터하여목적화합물인화합물 3-B (16 g, 64%의수율)을
수득하였다.
MS(m/z, [M]+): 460.33 (3)둥근바닥플라스크에 3-B 15.5 g (33.7 mmol), 2-chloro-4,6-diphenyl-l,3,5-
Triazine 9 g (33.7 mmol),테트라키스 (트리페닐포스핀)팔라듐 [Pd(PPh3)4] 1.947 g (1.69 mmol),포타슘카보네이트 13.973 g (101.1 mmol)을 THF 170 mL,증류수 50 mL에 넣고 12시간동안가열환류하였다.반응이완결되면상온으로넁각하고 THF와증류수를· 분리한다음,메탄올 100 mL에분리된 THF를적가하며 결정화시킨후,생성된 고형물을여과하고,물과메탄올로세정하였다.이로부터수득한고형물을
진공오븐에서 건조하여화합물 3 (12 g, 63%의수율)을수득하였다.
MS(m/z, [M]+): 565.62 합성예 3 :화합물 7의합성
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[반응식]
둥근바닥클라스크에 3-B 12 g (26.23 mmol), 2-[ 1 ,1 '-biphenyl]-4-yl-4-chloro-6- phenyl-1 ,3,5-Triazine 9 g (26.23 mmol),테트라키스 (트리페닐포스편)팔라듐 [Pd(PPh3)4] 1.513 g (1.31 mmol),포타슘카보네이트 10.877 g (78.70 mmol)을 THF 130 mL,증류수 40 mL에 넣고 12시간동안가열환류하였다.반응이 완결되면상온으로냉각하고 THF와증류수를분리한다음,메탄올 100 mL에 분리된 THF를적가하며 결정화시킨 후，생성된고형물을여과하고,물과메탄올로세정하였다.이로부터수득한 고형물을진공오븐에서 건조하여화합물 7 (12 g, 71%의수율)을수득하였다.
MS(m/z, [M]+): 641.71 비교합성예 1:화합물 <:의합성
[반응식]
(1)둥근바닥플라스크에중간체 C-l(PhaimaBlock, cas: 1472062-94-4) 12 g (34.98 mmol), 3-chlorophenyl boronic acid 5.457 g (34.98 mmol),탄산칼륨 14.5g (104.93 mmol), Pd(PPh3)4(Tetrakis- (triphenylphosphine) palladium(O)) 2.021 g (1.75 mmol)을
테트라하이드로퓨란 150mL,물 75 mL에 넣어준후，질소기류하에서 12시간동안 70°C로가열하였다.이로부터수득한혼합물을메탄올 500 mL에 가하여 결정화된 고형분을여과한후，다이클로로벤젠에녹여실리카겔/셀라이트로여과하고，유기 용매를적당량제거한후,메탄올로재결정하여 화합물 C-2 (12 g, 82%의수율)을
2019/132399 1»（：1^1{2018/016246
45 수득하였다.
MS(m/z, [M]+): 419.12
(2)둥근바닥플라스크에중간체 C-2 12 g (28.63 mmol), B-3-dibenzofuranyl- Boronic acid, 6.072 g (28.63 mmol),탄산칼륨 11.871 g (85.89 mmol), Pd(PPh3)4(Tetrakis- (triphenylphosphine) palladium(O)) 1.654 g (1.43 mmol)을테트라하이드로퓨란 130 mL,물 40 mL에 넣어준후,질소기류하에서 12시간동안 70°C로가열하였다.이로부터 수득한혼합물을메탄올 500 mL에가하여 결정화된고형분을여과한후, 다이클로로벤젠에 녹여실리카겔/셀라이트로여과하고，유기용매를적당량제거한 후，메탄올로재결정하여 화합물 C (10 g，63%의수율)을수득하였다.
MS(m/z, [M]+): 551.20
(제2유기광전자소자용화합물)
합성예 4 :화합물 C-99의합성
질소분위기하교반기가부착된 500 mL둥근바닥플라스크에 3 -브로모-: N- 바이페닐카바졸 15.00 g(37.66mmol), 3 -보로닉에스터- N-바이페닐카바졸 16.77 g(37.66 mmol)및테트라하이드로퓨란:톨루엔 (1:1) 200mL와 2M-탄산칼륨수용액 100mL를 혼합한후，테트라키스트리페닐포스핀팔라둠 (0) 2.18 g(1.88mmol)을넣고
질소기류하에서 12시간동안가열환류하였다.반응종결후반응물을메탄올에 부어고형물을여과한다음,이로부터수득한고형물을물과메탄올로충분히 세정하고건조하였다.이로부터수득한결과물을 500mL의클로로벤젠에 고형물을 녹인다음용액을실리카겔필터하고용매를완전히 제거하고, 400mL의톨루엔에 가열하여녹인다음재결정 하여화합물 C-99 16.54 g (수율 69%)을수득하였다.
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46
[화학식 0-99]
(유기발광소자의 제작)
실시예 1:
ITO (Indium tin oxide)가 1500 A두께로박막코팅된유리 기판을증류수 초음파로세척하였다.증류수세척이 끝나면 이소프로필알코올，아세톤,메탄올 등의용제로초음파세척을하고건조시킨후플라즈마세정기로이송시킨다음 산소플라즈마를이용하여상기 기판을 10분간세정 한후진공증착기로기판을 이송하였다.이렇게준비된 ITO투명 전극을양극으로사용하여 ITO기판상부에 화합물 A을진공증착하여 700 A두께의 정공주입층을형성하고상기주입층 상부에 화합물 B를 50A의두께로증착한후,화합물 C를 1020A의두께로 증착하여 정공수송층을형성하였다.정공수송층상부에 화합물 C-99및화합물 2를 동시에호스트로사용하고도판트로 Ir(ppy)3를 7wt%로도핑하여 진공증착으로 400 A두께의 발광증을형성하였다.여기서 화합물 C-99와화합물 2은 6:4중량비로 사용되었으며,하기 실시예의 경우별도로비율을기술하였다.이어서상기 발광층 상부에 화합물 D와 Liq를동시에 1:1비율로진공증착하여 300A두께의 전자수송층을형성하고상기 전자수송층상부에 Liq l5A과 A1 1200A을순차적으로 진공증착하여음극을형성함으로써 유기발광소자를제작하였다.
상기유기발광소자는 5층의유기 박막층을가지는구조로되어 있으며, 구체적으로다음과같다.
ITO/화합물 A(700A)/화합물 B(50A)/화합물 C(1020A)/EML [화합물 C- 99:화합물 2:Ir(ppy)3(7wt%)](400A)/화합물 D:Liq(300 A)/Liq(15 A)/A1(1200A)의구조로
2019/132399 1»(：1^1{2018/016246
47 제작하였다.
화합물 N4,N4'-dipllenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)biphenyl-4,4'-
화합물 0: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-
911-011(凡611-2-31고뇨16
화합물 I): 8-(4-(4,6-di(naphthalen-2-yl)- 1 ,3 ,5 - triazin-2-yl)phenyl)quinolone 실시예 2.실시예 3및비교예 1
하기 표 1에 기재된바와같이 제 1호스트및제 2호스트를사용하여실시예
1과동일한방법으로실시예 2,실시예 3및 비교예 1의유기발광소자를제작하였다. 평가
실시예 1내지 실시예 3,그리고비교예 1에따른유기발광소자의 효과를 다음과같이 평가하였다. 구체적인측정방법은하기와같다.
(1)구동전압측정
전류-전압계 (1＜ 加 6 2400)를이용하여 15 111쇼/0고2에서각소자의구동전압을 측정하여 결과를얻었다.
(2)전압변화에 따른전류밀도의 변화측정
제조된유기발광소자에 대해,전압을
부터 10¥까지상승시키면서 전류- 전압계 (1¾油! 6 2400)를이용하여단위소자에흐르는전류값을측정하고,측정된 전류값을면적으로나누어 결과를얻었다.
(3)전압변화에 따른휘도변화측정
제조된유기발광소자에 대해,전압을 0 부터 10¥까지상승시키면서
휘도계 ( 止0^ 03-1000시를이용하여 그때의 휘도를측정하여 결과를얻었다.
(4)발광효율측정
상기 (2)및 (3)로부터측정된휘도와전류밀도및전압을이용하여동일 전류밀도 (10«1 ¥2)의 전류효율 /시을계산하였다.
(5)외부양자효율여(3피
제조된유기발광소자에 대해,모든소자는흡습제와함께봉지하여
2019/132399 1»（可/1012018/016246
48 평가하였으며, IPCE measurement system을이용하여 이용하여요구휘도（） 00 cd/m2）일 때의 EQE를측정하였다.
[표 1]
Claims
[화학식 1]
상기 화학식 1에서
X1은 0또는 이고，
II1내지 II8은각각독립적으로수소,중수소,시아노기，치환또는비치환된 01내지 010알킬기,치환또는비치환된 C6내지 020아릴기,또는치환또는 비치환된 C2내지 030해테로고리기이고,
상기묘6및모7중적어도하나는 1개 이상의 질소원자를포함하는치환 또는비치환된 02내지 030헤테로고리기이고,
상기모5내지묘8중적어도하나는하기 화학식 2로표현되고，
[화학식 2]
상기화학식 2에서,
X2는 0또는 £이고,
^내지묘13은각각독립적으로수소,중수소，시아노기，치환또는비치환된 01내지 010알킬기,치환또는비치환된 C6내지 020아릴기，또는치환또는 비치환된 02내지 030헤테로고리기이다.
【청구항 2]
제 1항에 있어서,
상기요6및모7중적어도하나는치환또는비치환된피리디닐기，치환또는
2019/132399 1»(그1^1{2018/016246
50 비치환된피리미디닐기，치환또는비치환된트리아지닐기，치환또는비치환된 퀴나졸리닐기또는치환또는비치환된벤조티에노피리미디닐기인유기 광전자 소자용화합물.
【청구항 3】
제 1항에 있어서,
상기 #및 II7중적어도하나는하기화학식 3으로표현되는유기 광전자 소자용화합물:
[화학식 3]
상기 화학식 3에서，
X3내지 X5는각각독립적으로 X또는여 은수소또는 01내지 010 알킬기임）이고,
X3내지 X5중적어도하나이상은 이고，
묘14및모15는각각독립적으로수소，중수소，시아노기,치환또는비치환된 01내지 010알킬기，치환또는비치환된 06내지 020아릴기，또는치환또는 비치환된 02내지 030헤테로고리기이다.
【청구항 4]
제 3항에 있어서，
상기 X3내지 X5중적어도둘이상은 X인유기 광전자소자용화합물.
【청구항 5】
제 3항에 있어서,
상기묘14및 II15는각각독립적으로하기그룹 I에서선택된어느하나의 치환기인유기광전자소자용화합물.
\¥0 2019/132399 1»（：1^1{2018/016246
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[그룹 I]
【청구항 6]
제 1항에 있어서，
상기화학식 2는하기화학식 2-1또는화학식 2-2로표현되는유기 광전자 소자용화합물:
[화학식 2-1] [화학식 2-2]
상기화학식 2-1내지 화학식 2-2에서,
X2는각각독립적으로 0또는 이고,
내지 3은각각독립적으로수소，중수소,시아노기，치환또는비치환된 01내지 010알킬기,치환또는비치환된 06내지 020아릴기,또는치환또는 비치환된 02내지 030헤테로고리기이다.
【청구항 7】
제 1항의유기 광전자소자용화합물을포함하는유기광전자소자용조성물.
【청구항 8】
제 7항에 있어서，
상기유기 광전자소자용조성물은하기화학식 4로표현되는유기 광전자 소자용화합물또는하기 화학식 5로표현되는모이어티와하기 화학식 6으로 표현되는모이어티의조합으로이루어진유기 광전자소자용화합물을더포함하는 유기 광전자소자용조성물:
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［화학식 4］
상기화학식 4에서，
및 는각각독립적으로단일결합，치환또는비치환된 06내지 030 아릴렌기，치환또는비치환된 02내지 030헤테로아릴렌기，또는이들의조합이고, 쇼］·1및쇼!·2는각각독립적으로치환또는비치환된 06내지 030아릴기，치환 또는비치환된 02내지 030해테로고리기 ,또는이들의 조합이고，
及）6내지요21은각각독립적으로수소，중수소，치환또는비치환된 01내지 020알킬기,치환또는비치환된 06내지 030아릴기,치환또는비치환된 02내지 050헤테로고리기,또는이들의조합이고,
은 0내지 2의 정수중하나이고，
［화학식 5］ ［화학식 6］
상기화학식 5및 6에서,
및 는각각독립적으로단일결합,치환또는비치환된 06내지 030 아릴렌기,치환또는비치환된 02내지 030헤테로아릴렌기,또는이들의조합이고, 쇼戶및쇼/는각각독립적으로치환또는비치환된 06내지 030아릴기，치환 또는비치환된 02내지 030헤테로고리기，또는이들의 조합이고,
II22내지묘25는각각독립적으로수소，중수소,치환또는비치환된 01내지 020알킬기,치환또는비치환된 06내지 050아릴기,치환또는비치환된 02내지
2019/132399 1»（그 ^1{2018/016246
53
050헤테로고리기또는이들의조합이고,
상기 화학식 5의 인접한두개의 *는상기 화학식 6의두개의 *와결합하여 융합고리를형성하고,상기화학식 5에서융합고리를형성하지 않은 *는각각 독립적으로
이고,
수소,중수소,치환또는비치환된 01내지 010알킬기,치환또는 비치환된 06내지 012아릴기 ,치환또는비치환된 02내지 012헤테로고리기 , 또는이들의조합이다.
【청구항 9】
제 8항에 있어서,
상기 화학식 4의쇼!:1및쇼는각각독립적으로치환또는비치환된페닐기, 치환또는비치환된바이페닐기，치환또는비치환된터페닐기，치환또는비치환된 나프틸기,치환또는비치환된안트라세닐기,치환또는비치환된트리페닐레닐기, 치환또는비치환된피.리디닐기，치환또는비치환된피리미디닐기，치환또는 비치환된퀴나졸일기,치환또는비치환된이소퀴나졸일기,치환또는비치환된 디벤조티오펜일기 ,치환또는비치환된디벤조퓨란일기，치환또는비치환된 카바졸일기,치환또는비치환된플루오레닐기또는이들의조합인유기 광전자 소자용조성물:
【청구항 10】
제 8항에 있어서，
상기화학식 4는하기 그룹 II에나열된구조중하나이고,상기
- - 2는하기그룹 III에 나열된치환기중하나인유기광전자소자용조성물:
2019/132399 1»(：1/1(1公018/016246
54
[그룹 II ]
[그룹 III]
상기 그룹 II 및그룹이에서, *은연결지점이다.
【청구항 11】
제 10항에 있어서,
각각독립적으로상기그룹 III의 8-1내지：8-4중어느하나로표현되는유기 광전자소자용조성물.
2019/132399 1»（：1/10公018/016246
55
【청구항 12】
제 8항에 있어서，
상기화학식 5로표현되는모이어티와상기화학식 6으로표현되는 모이어티의조합으로이루어진화합물은하기 화학식 7-1내지화학식 7-5중 적어도하나로표현되는유기 광전자소자용조성물:
[화학식 7-1] [화학식 7-2]
상기화학식 7-1내지 7-5에서,
V3및 는각각독립적으로단일결 치환또는비치환된 06내지 030 아릴렌기,치환또는비치환된 02내지 030헤테로아릴렌기또는이들의 조합이고，
\¥0 2019/132399 1»（：1^1{2018/016246
56 쇼戶및쇼］·4는각각독립적으로치환또는비치환된 06내지 030아릴기，치환 또는비치환된 02내지 030헤테로고리기또는이들의조합이고，
모22내지 5는각각독립적으로수소，중수소,치환또는비치환된 01내지 020알킬기，치환또는비치환된 06내지 050아릴기，치환또는비치환된 02내지 050헤테로고리기또는이들의 조합이다.
【청구항 13】
제 8항에 있어서,
상기 하기화학식 1로표현되는유기 광전자소자용화합물과상기화학식 4로표현되는유기 광전자소자용화합물은 3:7내지 6:4의 중량비로포함되는유기 광전자소자용조성물.
【청구항 14】
서로마주하는양극과음극，그리고
상기 양극과상기 음극사이에위치하는적어도한층의유기층을포함하고， 상기 유기층은제 1항내지 제 6항중어느한항에따른유기 광전자소자용 화합물또는제 7항내지 제 13항중어느한항에 따른유기 광전자소자용 조성물을포함하는유기 광전자소자.
【청구항 15】
제 14항에 있어서，
상기유기층은발광층을포함하고,
상기유기 광전자소자용조성물은상기 발광층의 호스트로서포함되는유기 광전자소자.
【청구항 16】
제 14항에 따른유기 광전자소자를포함하는표시장치.
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| KR1020170181462A KR102162404B1 (ko) | 2017-12-27 | 2017-12-27 | 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 |
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Cited By (3)
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| CN113993863A (zh) * | 2019-10-08 | 2022-01-28 | Lt素材株式会社 | 杂环化合物、包括其的有机发光二极管、用于有机发光二极管有机层的组成物以及制造有机发光二极管的方法 |
| WO2022124367A1 (ja) * | 2020-12-11 | 2022-06-16 | 日鉄ケミカル＆マテリアル株式会社 | 有機電界発光素子用材料及び有機電界発光素子 |
| US11482681B2 (en) | 2018-07-27 | 2022-10-25 | Idemitsu Kosan Co., Ltd. | Compound, material for organic electroluminescence element, organic electroluminescence element, and electronic device |
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| KR102275039B1 (ko) * | 2019-10-08 | 2021-07-08 | 엘티소재주식회사 | 유기 발광 소자, 이의 제조 방법 및 유기 발광 소자의 유기물층용 조성물 |
| KR102318675B1 (ko) * | 2019-12-24 | 2021-11-01 | 엘티소재주식회사 | 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 유기 발광 소자의 유기물층용 조성물 및 유기 발광 소자의 제조 방법 |
| KR102319692B1 (ko) * | 2019-12-26 | 2021-11-02 | 엘티소재주식회사 | 헤테로고리 화합물, 이를 포함하는 유기 발광 소자 및 유기 발광 소자의 유기물층용 조성물 |
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| KR20190079339A (ko) | 2019-07-05 |
| KR102162404B1 (ko) | 2020-10-06 |
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