WO2022231285A1 - Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device, and display device - Google Patents
Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device, and display device Download PDFInfo
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- WO2022231285A1 WO2022231285A1 PCT/KR2022/005980 KR2022005980W WO2022231285A1 WO 2022231285 A1 WO2022231285 A1 WO 2022231285A1 KR 2022005980 W KR2022005980 W KR 2022005980W WO 2022231285 A1 WO2022231285 A1 WO 2022231285A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 113
- 230000005693 optoelectronics Effects 0.000 title claims abstract description 76
- 239000000203 mixture Substances 0.000 title claims abstract description 28
- 239000000126 substance Substances 0.000 claims abstract description 45
- 239000010410 layer Substances 0.000 claims description 58
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 30
- 229910052805 deuterium Inorganic materials 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 239000012044 organic layer Substances 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- -1 dibenzofuranyl group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 11
- 125000006267 biphenyl group Chemical group 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 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 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
- 125000005580 triphenylene group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 description 65
- 238000003786 synthesis reaction Methods 0.000 description 65
- 230000005525 hole transport Effects 0.000 description 21
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- 230000000052 comparative effect Effects 0.000 description 17
- 239000002019 doping agent Substances 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
- 238000006467 substitution reaction Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
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- 229940126062 Compound A Drugs 0.000 description 9
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 8
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- 125000005842 heteroatom Chemical group 0.000 description 7
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
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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 6
- 238000010992 reflux Methods 0.000 description 6
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- 239000003446 ligand Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
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- 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 5
- 238000005406 washing Methods 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- CXHXFDQEFKFYQJ-UHFFFAOYSA-N 2-bromo-4-chloro-1-iodobenzene Chemical compound ClC1=CC=C(I)C(Br)=C1 CXHXFDQEFKFYQJ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
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- 229920001940 conductive polymer Polymers 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 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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- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- ROJJKFAXAOCLKK-UHFFFAOYSA-N 1-bromo-4-chloro-2-iodobenzene Chemical compound ClC1=CC=C(Br)C(I)=C1 ROJJKFAXAOCLKK-UHFFFAOYSA-N 0.000 description 2
- MROVZCRMXJZHCN-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2-hydroxyethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCCO)C=CC=1 MROVZCRMXJZHCN-UHFFFAOYSA-N 0.000 description 2
- VVPGEFWZAXBZHR-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]sulfanyl-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)SC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 VVPGEFWZAXBZHR-UHFFFAOYSA-N 0.000 description 2
- NRLQBVLOUUPAMI-UHFFFAOYSA-N 8-[3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxybenzoyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)N2CCC3(CNC(O3)=O)CC2)C=CC=1 NRLQBVLOUUPAMI-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910052693 Europium Inorganic materials 0.000 description 2
- 229910052771 Terbium Inorganic materials 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910052775 Thulium Inorganic materials 0.000 description 2
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 2
- KDSYNTPPPISIJB-UHFFFAOYSA-N [3-[[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxymethyl]phenyl]-(3-fluoro-4-hydroxypyrrolidin-1-yl)methanone Chemical compound NCc1cc(OCc2cccc(c2)C(=O)N2CC(O)C(F)C2)nc(c1)C(F)(F)F KDSYNTPPPISIJB-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
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- 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 2
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- HONNWTDYWUAZJF-UHFFFAOYSA-N tert-butyl 4-[2-[4-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyindol-1-yl]acetyl]piperazine-1-carboxylate Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC1=C2C=CN(C2=CC=C1)CC(=O)N1CCN(CC1)C(=O)OC(C)(C)C HONNWTDYWUAZJF-UHFFFAOYSA-N 0.000 description 2
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- 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
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- CUDDLYMAQMEZDS-UHFFFAOYSA-N 2-[3-[3-(9,9-dimethylfluoren-2-yl)phenyl]phenyl]-4,6-diphenyl-1,3,5-triazine Chemical compound CC1(C)C2=CC=CC=C2C2=C1C=C(C=C2)C1=CC=CC(=C1)C1=CC(=CC=C1)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1 CUDDLYMAQMEZDS-UHFFFAOYSA-N 0.000 description 1
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000000304 alkynyl 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
- 150000001450 anions Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 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
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- MFMVRILBADIIJO-UHFFFAOYSA-N benzo[e][1]benzofuran Chemical compound C1=CC=C2C(C=CO3)=C3C=CC2=C1 MFMVRILBADIIJO-UHFFFAOYSA-N 0.000 description 1
- LJOLGGXHRVADAA-UHFFFAOYSA-N benzo[e][1]benzothiole Chemical compound C1=CC=C2C(C=CS3)=C3C=CC2=C1 LJOLGGXHRVADAA-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 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
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 238000009835 boiling Methods 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
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- YGHUUVGIRWMJGE-UHFFFAOYSA-N chlorodimethylsilane Chemical compound C[SiH](C)Cl YGHUUVGIRWMJGE-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 125000005105 dialkylarylsilyl group Chemical group 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 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
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 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
- 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
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 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
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N isonitrile group Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229940091250 magnesium supplement Drugs 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 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
- 125000001791 phenazinyl group Chemical class 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
- 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
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 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
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 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
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000005106 triarylsilyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- It relates to a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device.
- An organic optoelectronic diode is a device capable of converting electrical energy and optical energy.
- Organic optoelectronic devices can be roughly divided into two types according to their operating principles.
- One is a photoelectric device that generates electrical energy as excitons formed by light energy are separated into electrons and holes, and electrons and holes are transferred to different electrodes, and the other is electrical energy by supplying voltage or current to the electrode
- It is a light emitting device that generates light energy from
- Examples of the organic optoelectronic device include an organic optoelectronic device, an organic light emitting device, an organic solar cell, and an organic photo conductor drum.
- organic light emitting diodes have recently attracted much attention due to an increase in demand for flat panel display devices.
- An organic light emitting device is a device that converts electrical energy into light, and the performance of the organic light emitting device is greatly affected by an organic material positioned between electrodes.
- One embodiment provides a compound for an organic optoelectronic device capable of realizing a high-efficiency and long-life organic optoelectronic device.
- Another embodiment provides a composition for an organic optoelectronic device comprising the compound for an organic optoelectronic device.
- Another embodiment provides an organic optoelectronic device comprising the compound for an organic optoelectronic device or a composition for an organic optoelectronic device.
- Another embodiment provides a display device including the organic optoelectronic device.
- a compound for an organic optoelectronic device represented by a combination of Chemical Formulas 1 and 2 below.
- X 1 is O or S
- L 1 To L 3 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group
- Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
- a1*, a2*, b1*, b2*, b3* and b4* are each independently a linking carbon (C) or CR a ;
- a 1 * and a 2 * are connected to adjacent two of b 1 *, b 2 *, b 3 * and b 4 *, respectively;
- R a and R 1 to R 3 are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group,
- R 4 and R 5 are each independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,
- n1 is one of integers from 1 to 4,
- n2 is an integer of 1 or 2
- n3 is one of integers from 1 to 3.
- composition for an organic optoelectronic device comprising a first compound and a second compound.
- the first compound may be the same as described above, and the second compound may be a compound for an organic optoelectronic device represented by Chemical Formula 3 below.
- X 2 is O, S, NL a -R b , CR c R d or SiR e R f ,
- L a is a single bond, or a substituted or unsubstituted C6 to C12 arylene group
- R b , R c , R d , R e , R f and R 6 are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
- n6 is one of integers from 1 to 4,
- A is any one selected from the rings listed in Group II,
- X 3 is O or S
- R 7 to R 14 are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
- n7, n9, n12 and n14 are each independently an integer of 1 to 4,
- n8, n10, n11 and n13 are each independently an integer of 1 or 2
- At least one of R b and R 6 to R 14 is a group represented by the following formula (a),
- Z 1 to Z 3 are each independently N or CR g ,
- At least two of Z 1 to Z 3 are N,
- R g is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
- L 4 To L 6 are each independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group,
- Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,
- it 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 comprises the compound for an organic optoelectronic device or a composition for an organic optoelectronic device An organic optoelectronic device is provided.
- a display device including the organic optoelectronic device is provided.
- a high-efficiency, long-life organic optoelectronic device can be realized.
- FIG. 1 is a cross-sectional view illustrating an organic light emitting diode according to an exemplary embodiment.
- At least one hydrogen in a substituent or compound is deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or Unsubstituted C1 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 heterocycloalkyl group, C6 to C30 aryl group, C2 to C30 It means substituted with a heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.
- substitution means that at least one hydrogen in a substituent or compound is deuterium, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 It means substituted with a heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a cyano group.
- substitution means that at least one hydrogen in a substituent or compound is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a cyano group.
- substitution means that at least one hydrogen in a substituent or compound is substituted with deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, or a cyano group.
- substitution means that at least one hydrogen in a substituent or compound is substituted with deuterium, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group means it has been
- unsubstituted means that a hydrogen atom remains as a hydrogen atom without being substituted with another substituent.
- hydrofluorescence substitution may include deuterium substitution (-D) or "tritium substitution (-T).
- hetero means that one functional group contains 1 to 3 heteroatoms selected from the group consisting of N, O, S, P and Si, and the remainder is carbon. .
- aryl group is a concept that encompasses a group having one or more hydrocarbon aromatic moieties, and all elements of the hydrocarbon aromatic moiety have p-orbitals, and these p-orbitals are conjugated.
- It contains a form that forms, for example, a phenyl group, a naphthyl group, etc., and includes a form in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, such as a biphenyl group, a terphenyl group, a quaterphenyl group, etc., and two or more hydrocarbon aromatic moieties They may include a fused non-aromatic fused ring, such as a fluorenyl group, directly or indirectly.
- Aryl groups include monocyclic, polycyclic or fused ring polycyclic (ie, rings that share adjacent pairs of carbon atoms) functional groups.
- heterocyclic group is a higher concept including a heteroaryl group, and instead of carbon (C), N, O, It means containing at least one hetero atom selected from the group consisting of S, P and Si.
- C carbon
- N nitrogen
- O oxygen
- the heterocyclic group is a fused ring, the entire heterocyclic group or each ring may include one or more heteroatoms.
- heteroaryl group means containing at least one hetero atom selected from the group consisting of N, O, S, P and Si in the aryl group.
- Two or more heteroaryl groups may be directly connected through a sigma bond, or when the heteroaryl group includes two or more rings, the two or more rings may be fused to each other.
- each ring may include 1 to 3 heteroatoms.
- a substituted or unsubstituted C6 to C30 aryl group includes a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or Unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted p-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted or unsubstituted o- Terphenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted benzophenanthrenyl group, substituted or unsubstituted triphenylene group, substituted
- a substituted or unsubstituted C2 to C30 heterocyclic group is a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, A substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted A substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group,
- the hole property refers to a property capable of forming a hole by donating electrons when an electric field is applied. It refers to a property that facilitates the movement of holes formed in the anode and in the light emitting layer.
- the electronic property refers to a property that can receive electrons when an electric field is applied. It has conduction properties along the LUMO level, so electrons formed in the cathode are injected into the light emitting layer, electrons formed in the light emitting layer are moved to the cathode, and in the light emitting layer. properties that facilitate movement.
- the compound for an organic optoelectronic device is represented by a combination of Chemical Formulas 1 and 2 below.
- X 1 is O or S
- L 1 To L 3 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group
- Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
- a1*, a2*, b1*, b2*, b3* and b4* are each independently a linking carbon (C) or CR a ;
- a 1 * and a 2 * are connected to adjacent two of b 1 *, b 2 *, b 3 * and b 4 *, respectively;
- R a and R 1 to R 3 are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group,
- R 4 and R 5 are each independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,
- n1 is one of integers from 1 to 4,
- n2 is an integer of 1 or 2
- n3 is one of integers from 1 to 3.
- the high glass transition temperature due to these structural features maintains a stable film against Joule heat generated during device driving to ensure stable device characteristics and realize devices with excellent lifetime.
- the device stability is increased in the device manufacturing process using
- the moiety represented by Formula 1 may be represented by any one of Formulas 1A to 1C below depending on the fusion direction of naphtho formed by connecting *.
- X 1 , R 1 , R 2 , n1 , n2 , a1* and a2* are the same as described above.
- the combination of Chemical Formulas 1 and 2 may be represented by any one of the following Chemical Formulas 2A to 2F according to a specific combination position.
- X 1 , L 1 to L 3 , Ar 1 , Ar 2 and R 1 to R 5 , and n1 to n3 are the same as described above,
- R a1 to R a4 are each independently the same as defined above for R a .
- Formula 2A may be represented by any one of Formulas 2A-A, Formula 2A-B, and Formula 2A-C.
- Chemical Formula 2B may be represented by any one of Chemical Formula 2B-A, Chemical Formula 2B-B, and Chemical Formula 2B-C.
- Chemical Formula 2C may be represented by any one of Chemical Formula 2C-A, Chemical Formula 2C-B, and Chemical Formula 2C-C.
- Chemical Formula 2D may be represented by any one of Chemical Formula 2D-A, Chemical Formula 2D-B, and Chemical Formula 2D-C.
- Formula 2E may be represented by any one of Formulas 2E-A, Formula 2E-B, and Formula 2E-C.
- Formula 2F may be represented by any one of Formula 2F-A, Formula 2F-B, and Formula 2F-C.
- the combination of Formulas 1 and 2 may be represented by any one of Formulas 2C-A, 2C-B, 2C-C, 2F-A, 2F-B, and 2F-C.
- Formula 2C-A may be represented by, for example, any one of Formula 2C-A-1, Formula 2C-A-2, Formula 2C-A-3, and Formula 2C-A-4, depending on the specific substitution position of the amine group. have.
- Formula 2C-B may be represented by, for example, any one of Formula 2C-B-1, Formula 2C-B-2, Formula 2C-B-3, and Formula 2C-B-4, depending on the specific substitution position of the amine group. have.
- Formula 2C-C may be represented by, for example, any one of the following Formulas 2C-C-1, Formula 2C-C-2, Formula 2C-C-3, and Formula 2C-C-4, depending on the specific substitution position of the amine group. have.
- Formula 2F-A may be represented by, for example, any one of Formula 2F-A-1, Formula 2F-A-2, Formula 2F-A-3, and Formula 2F-A-4, depending on the specific substitution position of the amine group. have.
- Formula 2F-B may be represented by, for example, any one of Formula 2F-B-1, Formula 2F-B-2, Formula 2F-B-3, and Formula 2F-B-4, depending on the specific substitution position of the amine group. have.
- Formula 2F-C may be represented by, for example, any one of Formula 2F-C-1, Formula 2F-C-2, Formula 2F-C-3, and Formula 2F-C-4, depending on the specific substitution position of the amine group. have.
- X 1 , L 1 to L 3 , Ar 1 , Ar 2 , R 1 to R 5 , R a1 to R a4 and n1 to n3 are the same as described above.
- the combination of Chemical Formula 1 and Chemical Formula 2 includes Chemical Formula 2C-A-2, Chemical Formula 2C-B-2, Chemical Formula 2C-C-2, Chemical Formula 2C-A-3, Chemical Formula 2C-B-3, Any of Formula 2C-C-3, Formula 2F-A-2, Formula 2F-B-2, Formula 2F-C-2, Formula 2F-A-3, Formula 2F-B-3, or Formula 2F-C-3 can be expressed as one.
- Ar 1 and Ar 2 are each independently 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 anthracenyl group group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or It may be an unsubstituted dibenzothiophenyl group or a substituted or unsubstituted dibenzosilolyl group.
- Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted It may be a dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.
- Ar 1 and Ar 2 may each independently be any one selected from the substituents listed in Group I below.
- n15 is one of integers from 1 to 5
- n16 is one of integers from 1 to 7,
- n17 is one of integers from 1 to 3
- n18 is one of integers from 1 to 4,
- L 1 is a single bond
- the L 2 and L 3 may each independently be a single bond or a substituted or unsubstituted phenylene group.
- R 1 to R 3 , R a and R a1 to R a4 may each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.
- R 1 to R 3 , R a and R a1 to R a4 may each be hydrogen or deuterium.
- R 4 and R 5 may each independently represent a substituted or unsubstituted C1 to C5 alkyl group or a substituted or unsubstituted C6 to C12 aryl group.
- R 4 and R 5 may each independently represent a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, or a substituted or unsubstituted phenyl group.
- the compound for an organic optoelectronic device represented by a combination of Chemical Formulas 1 and 2 may include compounds listed in Group 1 below, but is not limited thereto.
- composition for an organic optoelectronic device includes a first compound and a second compound, wherein the first compound is the aforementioned compound for an organic optoelectronic device, and the second compound is an organic compound represented by the following Chemical Formula 3 It may be a compound for an optoelectronic device.
- X 2 is O, S, NL a -R b , CR c R d or SiR e R f ,
- L a is a single bond, or a substituted or unsubstituted C6 to C12 arylene group
- R b , R c , R d , R e , R f and R 6 are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
- n6 is one of integers from 1 to 4,
- A is any one selected from the rings listed in Group II,
- X 3 is O or S
- R 7 to R 14 are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
- n7, n9, n12 and n14 are each independently an integer of 1 to 4,
- n8, n10, n11 and n13 are each independently an integer of 1 or 2
- At least one of R b and R 6 to R 14 is a group represented by the following formula (a),
- Z 1 to Z 3 are each independently N or CR g ,
- At least two of Z 1 to Z 3 are N,
- R g is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
- L 4 To L 6 are each independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group,
- Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,
- the second compound has a structure substituted with a nitrogen-containing 6-membered ring.
- the second compound effectively extends the LUMO energy band by being substituted with a nitrogen-containing 6-membered ring, when used in the light emitting layer together with the above-described first compound, the balance of holes and electrons is increased by increasing the mobility and stability of the charge. It is possible to improve the luminous efficiency and lifespan characteristics of the device and lower the driving voltage.
- ring A of the second compound may be selected from the rings listed in Group II, and for example, the second compound may be represented by any one of the following Chemical Formulas 3-I to 3-XVI.
- Z 1 to Z 3 , R 6 , R 7 , L 4 to L 6 , Ar 3 , Ar 4 , n6 and n7 are the same as described above.
- X 2 , Z 1 to Z 3 , R 6 to R 9 , L 4 to L 6 , Ar 3 , Ar 4 , and n7 to n9 are the same as described above,
- n6 is one of integers from 1 to 3.
- X 2 , Z 1 to Z 3 , R 6 , R 8 , R 9 , L 4 to L 6 , Ar 3 , Ar 4 , n6 and n8 are the same as described above,
- n9 is one of integers from 1 to 3.
- X 2 , Z 1 to Z 3 , R 6 , R 10 to R 12 , L 4 to L 6 , Ar 3 , Ar 4 , n6, n10 and n11 are the same as described above,
- n12 is one of integers from 1 to 3.
- X 2 , X 3 , Z 1 to Z 3 , R 6 , R 13 , R 14 , L 4 to L 6 , Ar 3 , Ar 4 , n13 and n14 are the same as described above,
- n6 is one of integers from 1 to 3.
- X 2 , X 3 , Z 1 to Z 3 , R 6 , R 8 to R 13 , L 4 to L 6 , Ar 3 , Ar 4 , n6, n9, n10, n12 and n14 are the same as described above,
- n8, n10 and n13 are each independently 1;
- the second compound according to an embodiment may be represented by any one of Formula 3-II, Formula 3-III, and Formula 3-VI.
- the second compound according to a specific embodiment may be represented by any one of Formula 3-II-3, Formula 3-III-1, Formula 3-VI-1, and Formula 3-VI-3 below.
- X 2 , Z 1 to Z 3 , R 6 to R 9 , L 4 to L 6 , Ar 3 , Ar 4 and n6 to n8 are the same as described above.
- Ar 3 and Ar 4 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenantre Nyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, or substituted or unsubstituted dibenzosilol It could be the weather.
- Ar 3 and Ar 4 may each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.
- L 4 to L 6 may each independently represent a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.
- L 4 and L 5 may each independently represent a single bond or a substituted or unsubstituted phenylene group, and L 6 may be a single bond.
- R 6 to R 9 are each independently each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a substituted or unsubstituted C2 to C18 heterocyclic group.
- R 6 to R 9 may each independently be hydrogen, deuterium, a phenyl group, or a naphthyl group.
- X 2 is O, S, CR c R d or SiR e R f , and R c , R d , R e and R f are each independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted It may be a C6 to C20 aryl group.
- R c , R d , R e and R f may each independently represent a methyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.
- the second compound may be one selected from the compounds listed in Group 2 below.
- composition for an organic optoelectronic device includes Chemical Formula 2C-A-2, Chemical Formula 2C-A-3, Chemical Formula 2C-B-2, Chemical Formula 2C-C-2, and Chemical Formula 2F-A- 2, the first compound represented by any one of Formula 2F-A-3, and Formula 2F-B-2, and the second compound represented by Formula 3-III-1 may be included.
- the first compound and the second compound may be included, for example, in a weight ratio of 1:99 to 99:1.
- a weight ratio of 1:99 to 99:1 By being included in the above range, it is possible to implement bipolar characteristics by matching an appropriate weight ratio using the electron transport ability of the first compound and the hole transport ability of the second compound to improve efficiency and lifespan.
- it may be included in a weight ratio of about 10:90 to 90:10, about 20:80 to 80:20, such as about 20:80 to about 70:30, about 20:80 to about 60:40, And it may be included in a weight ratio of about 30:70 to about 60:40.
- it may be included in a weight ratio of 40:60, 50:50, or 60:40.
- the compound for an organic optoelectronic device or the composition for an organic optoelectronic device described above may be a composition further comprising a dopant.
- the dopant may be for example a phosphorescent dopant, for example a red, green or blue phosphorescent dopant, for example a red or green phosphorescent dopant.
- a dopant is a material that emits light by being mixed in a small amount in a compound or composition for an organic optoelectronic device.
- a material such as a metal complex that emits light by multiple excitation excitation to a triplet state or more may be used.
- the dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may include one or two or more kinds.
- the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant include Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. and organometallic compounds containing them.
- the phosphorescent dopant may be, for example, a compound represented by the following Chemical Formula Z, but is not limited thereto.
- M is a metal
- L 7 and X 4 are the same as or different from each other and are ligands forming a complex with M.
- M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or a combination thereof, and L 7 and X 4 are, for example, bi It may be a dentate ligand.
- Examples of the ligands represented by L 7 and X 4 may be selected from the formulas listed in Group A, but are not limited thereto.
- R 300 to R 302 are each independently hydrogen, deuterium, a halogen substituted or unsubstituted C1 to C30 alkyl group, a C1 to C30 alkyl substituted or unsubstituted C6 to C30 aryl group or halogen,
- R 303 to R 324 are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or an unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF 5 , a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30
- it may include a dopant represented by the following Chemical Formula V.
- R 101 to R 116 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or —SiR 132 R 133 R 134 ;
- R 132 to R 134 are each independently a C1 to C6 alkyl group
- At least one of R 101 to R 116 is a functional group represented by the following Chemical Formula V-1,
- L 100 is a bidentate ligand of a monovalent anion, and is a ligand that coordinates to iridium through a lone pair of electrons of carbon or heteroatom,
- n1 and m2 are each independently any one of an integer of 0 to 3
- m1 + m2 is any one of an integer of 1 to 3
- R 135 to R 139 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or —SiR 132 R 133 R 134 ;
- a dopant represented by the following Chemical Formula Z-1 may be included.
- rings A, B, C, and D each independently represent a 5- or 6-membered carbocyclic or heterocyclic ring;
- R A , RB , R C , and R D each independently represent mono-, di-, tri-, or tetra-substituted, or unsubstituted;
- R A , RB , R C , R D , R , and R' are each hydrogen, deuterium, halogen, an alkyl group, a cycloalkyl group, a heteroalkyl group, an arylalkyl group, an alkoxy group, an aryloxy group, an amino group, a silyl group, an alkenyl group , cycloalkenyl group, heteroalkenyl group, alkynyl group, aryl group, heteroaryl group, acyl group, carbonyl group, carboxylic acid group, ester group, nitrile group, isonitrile group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group independently selected from the group consisting of , and combinations thereof; any adjacent R A , R B , R C , R D , R , and R′ are optionally joined to form a ring; X B , X C
- the dopant according to an embodiment may be a platinum complex, for example, it may be represented by the following Chemical Formula VI.
- X 100 is selected from O, S and NR 131 ,
- R 117 to R 131 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or —SiR 132 R 133 R 134 ;
- R 132 to R 134 are each independently a C1 to C6 alkyl group
- At least one of R 117 to R 131 is -SiR 132 R 133 R 134 or a tert-butyl group
- the R 132 to R 134 are each independently a C1 to C6 alkyl group.
- the organic optoelectronic device is not particularly limited as long as it is a device capable of converting electrical energy and optical energy, and examples thereof include an organic photoelectric device, an organic light emitting device, an organic solar cell, and an organic photosensitive drum.
- FIG. 1 is a cross-sectional view illustrating an organic light emitting diode according to an exemplary embodiment.
- an organic light emitting device 100 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 of, for example, a conductor having a high work function 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 include, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO and Al or SnO 2 and Sb; conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene: PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto. it is not
- the cathode 110 may be made of, for example, a conductor having a low work function to facilitate electron injection, and may be made of, for example, a metal, a metal oxide, and/or a conductive polymer.
- the negative electrode 110 may include, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; and a multilayer structure material such as LiF/Al, LiO 2 /Al, LiF/Ca, LiF/Al, and BaF 2 /Ca, but is not limited thereto.
- the organic layer 105 may include the aforementioned compound for an organic optoelectronic device or a composition for an organic optoelectronic device.
- the organic layer 105 may include the emission layer 130 , and the emission layer 130 may include the aforementioned compound for an organic optoelectronic device or a composition for an organic optoelectronic device.
- composition for an organic optoelectronic device further comprising a dopant may be, for example, a green light-emitting composition.
- the emission layer 130 may include, for example, the above-described compound for an organic optoelectronic device or a composition for an organic optoelectronic device, respectively, as a phosphorescent host.
- the organic layer may further include a charge transport region in addition to the emission layer.
- the charge transport region may be, for example, the hole transport region 140 .
- the hole transport region 140 may further increase hole injection and/or hole mobility between the anode 120 and the emission layer 130 and block electrons.
- the hole transport region 140 may include a hole transport layer between the anode 120 and the light emitting layer 130 and a hole transport auxiliary layer between the light emitting layer 130 and the hole transport layer. At least one of the listed compounds may be included in at least one of the hole transport layer and the hole transport auxiliary layer.
- the charge transport region may be, for example, the electron transport region 150 .
- the electron transport region 150 may further increase electron injection and/or electron mobility between the cathode 110 and the emission layer 130 and block holes.
- the electron transport region 150 may include an electron transport layer between the cathode 110 and the light emitting layer 130 and an electron transport auxiliary layer between the light emitting layer 130 and the electron transport layer. At least one of the listed compounds may be included in at least one of the electron transport layer and the electron transport auxiliary layer.
- One embodiment may be an organic light emitting device including a light emitting layer as an organic layer.
- Another embodiment may be an organic light emitting device including a light emitting layer and a hole transport region as an organic layer.
- Another embodiment may be an organic light emitting device including a light emitting layer and an electron transport region as an organic layer.
- the organic light emitting device may include a hole transport region 140 and an electron transport region 150 in addition to the emission layer 130 as the organic layer 105 .
- the organic light emitting device may further include an electron injection layer (not shown), a hole injection layer (not shown), etc. in addition to the light emitting layer as the above-described organic layer.
- the organic light emitting device 100 After forming an anode or cathode on a substrate, the organic light emitting device 100 forms an organic layer by a dry film deposition method such as vacuum deposition, sputtering, plasma plating and ion plating, etc., and then a cathode or a It can be manufactured by forming an anode.
- a dry film deposition method such as vacuum deposition, sputtering, plasma plating and ion plating, etc.
- the above-described organic light emitting device may be applied to an organic light emitting display device.
- n-BuLi 104.5 ml g, 261.24 mmol
- Synthesis Example 1 SM-16 was used instead of SM-1, 1-bromo-4-chloro-2-iodobenzene was used instead of 2-bromo-4-chloro-1-iodobenzene, and SM-6 was used instead of SM-5.
- Compound 1-68 was synthesized according to Scheme 8 in the same manner as in Synthesis Example 1, except that .
- Compound A-17 was synthesized in the same manner as in step 4 of Synthesis Example 11, using 1.0 equivalents of Int-37 and Int-38, respectively.
- Compound A-37 was synthesized in the same manner as in step 4 of Synthesis Example 11, using 1.0 equivalents of Int-37 and Int-36, respectively.
- a glass substrate coated with a thin film of ITO Indium tin oxide was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning was performed with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a plasma cleaner. After cleaning the substrate using oxygen plasma for 10 minutes, the substrate was transferred to a vacuum evaporator.
- compound A doped with 3% NDP-9 commercially available from Novaled was vacuum-deposited on the top of the ITO substrate to form a hole injection layer with a thickness of 100 ⁇ , and Compound A was deposited thereon to a thickness of 1300 ⁇ to form a hole transport layer.
- Compound B was deposited on the hole transport layer to a thickness of 700 ⁇ to form a hole transport auxiliary layer.
- Compound 1-1 obtained in Synthesis Example 1 was used as a host on the hole transport auxiliary layer, and [Ir(piq) 2 acac] was doped at 2 wt% as a dopant to form an emission layer with a thickness of 400 ⁇ by vacuum deposition.
- compound C was deposited on the light emitting layer to a thickness of 50 ⁇ to form an electron transport auxiliary layer, and compound D and LiQ were simultaneously vacuum deposited at a weight ratio of 1:1 to form an electron transport layer having a thickness of 300 ⁇ .
- An organic light emitting diode was manufactured by sequentially vacuum-depositing 15 ⁇ of LiQ and 1200 ⁇ of Al on the electron transport layer to form a cathode.
- An organic light emitting diode was manufactured in the same manner as in Example 1, except that the host was changed as shown in Table 1 below.
- a glass substrate coated with a thin film of ITO Indium tin oxide was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning was performed with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, and transferred to a plasma cleaner. After cleaning the substrate for 10 minutes using oxygen plasma, the substrate was transferred to a vacuum evaporator.
- compound A doped with 3% NDP-9 commercially available from Novaled was vacuum-deposited on the top of the ITO substrate to form a hole injection layer with a thickness of 100 ⁇ , and Compound A was deposited thereon to a thickness of 1300 ⁇ to form a hole transport layer.
- Compound B was deposited on the hole transport layer to a thickness of 700 ⁇ to form a hole transport auxiliary layer.
- Compound 1-1 obtained in Synthesis Example 1 and compound A-17 obtained in Synthesis Example 12 were simultaneously used as a host on the hole transport layer, and doped with [Ir(piq) 2 acac] as a dopant at 2 wt% to a thickness of 400 ⁇ by vacuum deposition. of the light emitting layer was formed.
- Compound 1-1 and Compound A-17 were used in a weight ratio of 5:5.
- compound C was deposited on the light emitting layer to a thickness of 50 ⁇ to form an electron transport auxiliary layer, and compound D and LiQ were simultaneously vacuum deposited at a weight ratio of 1:1 to form an electron transport layer having a thickness of 300 ⁇ .
- An organic light emitting diode was manufactured by sequentially vacuum-depositing 15 ⁇ of LiQ and 1200 ⁇ of Al on the electron transport layer to form a cathode.
- An organic light emitting diode was manufactured in the same manner as in Example 19, except that the host was changed as shown in Table 2 below.
- the current flowing through the unit device was measured using a current-voltmeter (Keithley 2400) while the voltage was increased from 0V to 10V, and the measured current value was divided by the area to obtain a result.
- the luminance was measured at that time using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0V to 10V, and results were obtained.
- the luminous efficiency (cd/A) of the same current density (10 mA/cm 2 ) was calculated using the luminance, current density, and voltage measured from (1) and (2) above.
- the devices of Examples 1 to 29, and Comparative Examples 1 to 6 using a polaronics lifetime measurement system emit light with an initial luminance (cd/m 2 ) of 6,000 cd/m 2 , and in time The time when the luminance decreased to 95% compared to the initial luminance was measured as the T95 lifetime by measuring the decrease in luminance.
- Example 1 112 109
- Example 2 1-2 114 120
- Example 3 1-6 116 116
- Example 4 1-17
- Example 5 1-21
- Example 6 1-27
- Example 7 1-29
- Example 8 1-35
- Example 9 118
- Example 9 117 122
- Example 10 1-47
- Example 11 1-51
- Example 13 Example 13
- Example 14 1-101
- Example 15 Example 15
- Example 16 Example 16 1-127 113 108
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Abstract
The present invention relates to: a compound for an organic optoelectronic device, the compound being represented by a combination of chemical formula 1 and chemical formula 2; a composition comprising same for an organic optoelectronic device; an organic optoelectronic device; and a display device. The details of chemical formula 1 is as defined in the specification.
Description
유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치에 관한 것이다.It relates to a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device.
유기 광전자 소자(organic optoelectronic diode)는 전기 에너지와 광 에너지를 상호 전환할 수 있는 소자이다.An organic optoelectronic diode is a device capable of converting electrical energy and optical energy.
유기 광전자 소자는 동작 원리에 따라 크게 두 가지로 나눌 수 있다. 하나는 광 에너지에 의해 형성된 엑시톤(exciton)이 전자와 정공으로 분리되고 전자와 정공이 각각 다른 전극으로 전달되면서 전기 에너지를 발생하는 광전 소자이고, 다른 하나는 전극에 전압 또는 전류를 공급하여 전기 에너지로부터 광 에너지를 발생하는 발광 소자이다. Organic optoelectronic devices can be roughly divided into two types according to their operating principles. One is a photoelectric device that generates electrical energy as excitons formed by light energy are separated into electrons and holes, and electrons and holes are transferred to different electrodes, and the other is electrical energy by supplying voltage or current to the electrode It is a light emitting device that generates light energy from
유기 광전자 소자의 예로는 유기 광전 소자, 유기 발광 소자, 유기 태양 전지 및 유기 감광체 드럼(organic photo conductor drum) 등을 들 수 있다. Examples of the organic optoelectronic device include an organic optoelectronic device, an organic light emitting device, an organic solar cell, and an organic photo conductor drum.
이 중, 유기 발광 소자(organic light emitting diode, OLED)는 근래 평판 표시 장치(flat panel display device)의 수요 증가에 따라 크게 주목받고 있다. 유기 발광 소자는 전기 에너지를 빛으로 전환시키는 소자로서, 유기 발광 소자의 성능은 전극 사이에 위치하는 유기 재료에 의해 많은 영향을 받는다. Among them, organic light emitting diodes (OLEDs) have recently attracted much attention due to an increase in demand for flat panel display devices. An organic light emitting device is a device that converts electrical energy into light, and the performance of the organic light emitting device is greatly affected by an organic material positioned between electrodes.
일 구현예는 고효율 및 장수명 유기 광전자 소자를 구현할 수 있는 유기 광전자 소자용 화합물을 제공한다.One embodiment provides a compound for an organic optoelectronic device capable of realizing a high-efficiency and long-life organic optoelectronic device.
다른 구현예는 상기 유기 광전자 소자용 화합물을 포함하는 유기 광전자 소자용 조성물을 제공한다.Another embodiment provides a composition for an organic optoelectronic device comprising the compound for an organic optoelectronic device.
또 다른 구현예는 상기 유기 광전자 소자용 화합물 또는 유기 광전자 소자용 조성물을 포함하는 유기 광전자 소자를 제공한다.Another embodiment provides an organic optoelectronic device comprising the compound for an organic optoelectronic device or a composition for an organic optoelectronic device.
또 다른 구현예는 상기 유기 광전자 소자를 포함하는 표시 장치를 제공한다.Another embodiment provides a display device including the organic optoelectronic device.
일 구현예에 따르면, 하기 화학식 1 및 화학식 2의 조합으로 표현되는 유기 광전자 소자용 화합물을 제공한다.According to one embodiment, there is provided a compound for an organic optoelectronic device represented by a combination of Chemical Formulas 1 and 2 below.
[화학식 1] [화학식 2][Formula 1] [Formula 2]
상기 화학식 1 및 화학식 2에서,In Formula 1 and Formula 2,
X1은 O 또는 S이고,X 1 is O or S,
L1 내지 L3은 각각 독립적으로 단일 결합 또는 치환 또는 비치환된 C6 내지 C20 아릴렌기이고,L 1 To L 3 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C6 내지 C20 아릴기 또는 치환 또는 비치환된 C2 내지 C30 헤테로고리기이고,Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
a1*, a2*, b1*, b2*, b3* 및 b4*는 각각 독립적으로 연결 탄소 (C) 또는 CRa이고,a1*, a2*, b1*, b2*, b3* and b4* are each independently a linking carbon (C) or CR a ;
a1* 및 a2*는 각각 b1*, b2*, b3* 및 b4* 중 인접한 둘과 연결되고,a 1 * and a 2 * are connected to adjacent two of b 1 *, b 2 *, b 3 * and b 4 *, respectively;
Ra 및 R1 내지 R3은 각각 독립적으로 수소, 중수소, 할로겐기, 치환 또는 비치환된 C1 내지 C10 알킬기 또는 치환 또는 비치환된 C6 내지 C12 아릴기이고,R a and R 1 to R 3 are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group,
R4 및 R5는 각각 독립적으로 치환 또는 비치환된 C1 내지 C10 알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고,R 4 and R 5 are each independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,
n1은 1 내지 4의 정수 중 하나이고,n1 is one of integers from 1 to 4,
n2는 1 또는 2의 정수이며,n2 is an integer of 1 or 2,
n3은 1 내지 3의 정수 중 하나이다.n3 is one of integers from 1 to 3.
다른 구현예에 따르면, 제1 화합물, 및 제2 화합물을 포함하는 유기 광전자 소자용 조성물을 제공한다. According to another embodiment, there is provided a composition for an organic optoelectronic device comprising a first compound and a second compound.
상기 제1 화합물은 전술한 바와 같고, 상기 제2 화합물은 하기 화학식 3으로 표현되는 유기 광전자 소자용 화합물일 수 있다.The first compound may be the same as described above, and the second compound may be a compound for an organic optoelectronic device represented by Chemical Formula 3 below.
[화학식 3][Formula 3]
상기 화학식 3에서,In Formula 3,
X2는 O, S, N-La-Rb, CRcRd 또는 SiReRf이고,X 2 is O, S, NL a -R b , CR c R d or SiR e R f ,
La는 단일결합, 또는 치환 또는 비치환된 C6 내지 C12 아릴렌기이고,L a is a single bond, or a substituted or unsubstituted C6 to C12 arylene group,
Rb, Rc, Rd, Re, Rf 및 R6은 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C6 내지 C30 아릴기 또는 치환 또는 비치환된 C2 내지 C30 헤테로고리기이고,R b , R c , R d , R e , R f and R 6 are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
n6은 1 내지 4의 정수 중 하나이고,n6 is one of integers from 1 to 4,
A는 하기 그룹 Ⅱ에 나열된 고리 중에서 선택되는 어느 하나이고,A is any one selected from the rings listed in Group II,
[그룹 Ⅱ][Group II]
상기 그룹 Ⅱ에서,In group II,
*은 연결 지점이고,* is the connection point,
X3은 O 또는 S 이고,X 3 is O or S,
R7 내지 R14는 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C6 내지 C20 아릴기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로고리기이고,R 7 to R 14 are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
n7, n9, n12 및 n14는 각각 독립적으로 1 내지 4의 정수 중 하나이고,n7, n9, n12 and n14 are each independently an integer of 1 to 4,
n8, n10, n11 및 n13은 각각 독립적으로 1 또는 2의 정수이고,n8, n10, n11 and n13 are each independently an integer of 1 or 2,
Rb 및 R6 내지 R14 중 적어도 하나는 하기 화학식 a로 표현되는 기이고,At least one of R b and R 6 to R 14 is a group represented by the following formula (a),
[화학식 a][Formula a]
상기 화학식 a에서,In the above formula (a),
Z1 내지 Z3은 각각 독립적으로 N 또는 CRg이고,Z 1 to Z 3 are each independently N or CR g ,
Z1 내지 Z3 중 적어도 둘은 N이고,At least two of Z 1 to Z 3 are N,
Rg는 수소, 중수소, 치환 또는 비치환된 C1 내지 C30 알킬기, 또는 치환 또는 비치환된 C6 내지 C30 아릴기이고,R g is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
L4 내지 L6은 각각 독립적으로 단일 결합, 또는 치환 또는 비치환된 C6 내지 C30 아릴렌기이고,L 4 To L 6 are each independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group,
Ar3 및 Ar4는 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로아릴기이고,Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,
*는 연결 지점이다.* is the connection point.
또 다른 구현예에 따르면, 서로 마주하는 양극과 음극, 상기 양극과 상기 음극 사이에 위치하는 적어도 1층의 유기층을 포함하고, 상기 유기층은 상기 유기 광전자 소자용 화합물 또는 유기 광전자 소자용 조성물을 포함하는 유기 광전자 소자를 제공한다.According to another embodiment, it 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 comprises the compound for an organic optoelectronic device or a composition for an organic optoelectronic device An organic optoelectronic device is provided.
또 다른 구현예에 따르면, 상기 유기 광전자 소자를 포함하는 표시 장치를 제공한다.According to another embodiment, a display device including the organic optoelectronic device is provided.
고효율 장수명 유기 광전자 소자를 구현할 수 있다.A high-efficiency, long-life organic optoelectronic device can be realized.
도 1은 일 구현예에 따른 유기 발광 소자를 도시한 단면도이다.1 is a cross-sectional view illustrating an organic light emitting diode according to an exemplary embodiment.
<부호의 설명><Explanation of code>
100: 유기 발광 소자100: organic light emitting device
105: 유기층105: organic layer
110: 음극110: cathode
120: 양극120: positive electrode
130: 발광층130: light emitting layer
140: 정공 수송 영역140: hole transport region
150: 전자 수송 영역150: electron transport region
이하, 본 발명의 구현예를 상세히 설명하기로 한다. 다만, 이는 예시로서 제시되는 것으로, 이에 의해 본 발명이 제한되지는 않으며 본 발명은 후술할 청구범위의 범주에 의해 정의될 뿐이다.Hereinafter, embodiments of the present invention will be described in detail. However, this is provided as an example, and the present invention is not limited thereto, and the present invention is only defined by the scope of the claims to be described later.
본 명세서에서 "치환"이란 별도의 정의가 없는 한, 치환기 또는 화합물 중의 적어도 하나의 수소가 중수소, 할로겐기, 히드록실기, 아미노기, 치환 또는 비치환된 C1 내지 C30 아민기, 니트로기, 치환 또는 비치환된 C1 내지 C40 실릴기, C1 내지 C30 알킬기, C1 내지 C10 알킬실릴기, C6 내지 C30 아릴실릴기, C3 내지 C30 시클로알킬기, C3 내지 C30 헤테로시클로알킬기, C6 내지 C30 아릴기, C2 내지 C30 헤테로아릴기, C1 내지 C20 알콕시기, C1 내지 C10 트리플루오로알킬기, 시아노기, 또는 이들의 조합으로 치환된 것을 의미한다. As used herein, unless otherwise defined, at least one hydrogen in a substituent or compound is deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or Unsubstituted C1 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 heterocycloalkyl group, C6 to C30 aryl group, C2 to C30 It means substituted with a heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.
본 발명의 일 예에서, "치환"은 치환기 또는 화합물 중의 적어도 하나의 수소가 중수소, C1 내지 C30 알킬기, C1 내지 C10 알킬실릴기, C6 내지 C30 아릴실릴기, C3 내지 C30 시클로알킬기, C3 내지 C30 헤테로시클로알킬기, C6 내지 C30 아릴기, C2 내지 C30 헤테로아릴기, 또는 시아노기로 치환된 것을 의미한다. 또한, 본 발명의 구체적인 일 예에서, "치환"은 치환기 또는 화합물 중의 적어도 하나의 수소가 중수소, C1 내지 C20 알킬기, C6 내지 C30 아릴기, 또는 시아노기로 치환된 것을 의미한다. 또한, 본 발명의 구체적인 일 예에서, "치환"은 치환기 또는 화합물 중의 적어도 하나의 수소가 중수소, C1 내지 C5 알킬기, C6 내지 C18 아릴기, 시아노기로 치환된 것을 의미한다. 또한, 본 발명의 구체적인 일 예에서, "치환"은 치환기 또는 화합물 중의 적어도 하나의 수소가 중수소, 시아노기, 메틸기, 에틸기, 프로필기, 부틸기, 페닐기, 바이페닐기, 터페닐기 또는 나프틸기로 치환된 것을 의미한다. In one embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is deuterium, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 It means substituted with a heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a cyano group. In addition, in a specific embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a cyano group. In addition, in a specific embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is substituted with deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is substituted with deuterium, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group means it has been
본 명세서에서, “비치환”이란 수소 원자가 다른 치환기로 치환되지 않고 수소 원자로 남아있는 것을 의미한다.As used herein, “unsubstituted” means that a hydrogen atom remains as a hydrogen atom without being substituted with another substituent.
본 명세서에서, “수소 치환(-H)은 “중수소 치환(-D) 또는 “삼중수소 치환(-T)을 포함할 수 있다.In the present specification, "hydrogen substitution (-H) may include deuterium substitution (-D) or "tritium substitution (-T).
본 명세서에서 "헤테로"란 별도의 정의가 없는 한, 하나의 작용기 내에 N, O, S, P 및 Si로 이루어진 군에서 선택되는 헤테로 원자를 1 내지 3개 함유하고, 나머지는 탄소인 것을 의미한다.As used herein, unless otherwise defined, "hetero" means that one functional group contains 1 to 3 heteroatoms selected from the group consisting of N, O, S, P and Si, and the remainder is carbon. .
본 명세서에서 "아릴(aryl)기"는 탄화수소 방향족 모이어티를 하나 이상 갖는 그룹을 총괄하는 개념으로서, 탄화수소 방향족 모이어티의 모든 원소가 p-오비탈을 가지면서, 이들 p-오비탈이 공액(conjugation)을 형성하고 있는 형태, 예컨대 페닐기, 나프틸기 등을 포함하고, 2 이상의 탄화수소 방향족 모이어티들이 시그마 결합을 통하여 연결된 형태, 예컨대 바이페닐기, 터페닐기, 쿼터페닐기 등을 포함하며, 2 이상의 탄화수소 방향족 모이어티들이 직접 또는 간접적으로 융합된 비방향족 융합 고리, 예컨대 플루오레닐기 등을 포함할 수 있다.As used herein, the term "aryl group" is a concept that encompasses a group having one or more hydrocarbon aromatic moieties, and all elements of the hydrocarbon aromatic moiety have p-orbitals, and these p-orbitals are conjugated. It contains a form that forms, for example, a phenyl group, a naphthyl group, etc., and includes a form in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, such as a biphenyl group, a terphenyl group, a quaterphenyl group, etc., and two or more hydrocarbon aromatic moieties They may include a fused non-aromatic fused ring, such as a fluorenyl group, directly or indirectly.
아릴기는 모노시클릭, 폴리시클릭 또는 융합 고리 폴리시클릭(즉, 탄소원자들의 인접한 쌍들을 나눠 가지는 고리) 작용기를 포함한다.Aryl groups include monocyclic, polycyclic or fused ring polycyclic (ie, rings that share adjacent pairs of carbon atoms) functional groups.
본 명세서에서 "헤테로고리기(heterocyclic group)"는 헤테로아릴기를 포함하는 상위 개념으로서, 아릴기, 시클로알킬기, 이들의 융합고리 또는 이들의 조합과 같은 고리 화합물 내에 탄소 (C) 대신 N, O, S, P 및 Si로 이루어진 군에서 선택되는 헤테로 원자를 적어도 한 개 함유하는 것을 의미한다. 상기 헤테로고리기가 융합고리인 경우, 상기 헤테로고리기 전체 또는 각각의 고리마다 헤테로 원자를 한 개 이상 포함할 수 있다.In the present specification, "heterocyclic group" is a higher concept including a heteroaryl group, and instead of carbon (C), N, O, It means containing at least one hetero atom selected from the group consisting of S, P and Si. When the heterocyclic group is a fused ring, the entire heterocyclic group or each ring may include one or more heteroatoms.
일 예로 "헤테로아릴(heteroaryl)기"는 아릴기 내에 N, O, S, P 및 Si로 이루어진 군에서 선택되는 헤테로 원자를 적어도 한 개 함유하는 것을 의미한다. 2 이상의 헤테로아릴기는 시그마 결합을 통하여 직접 연결되거나, 상기 헤테로아릴기가 2 이상의 고리를 포함할 경우, 2 이상의 고리들은 서로 융합될 수 있다. 상기 헤테로아릴기가 융합고리인 경우, 각각의 고리마다 상기 헤테로 원자를 1 내지 3개 포함할 수 있다.For example, "heteroaryl group" means containing at least one hetero atom selected from the group consisting of N, O, S, P and Si in the aryl group. Two or more heteroaryl groups may be directly connected through a sigma bond, or when the heteroaryl group includes two or more rings, the two or more rings may be fused to each other. When the heteroaryl group is a fused ring, each ring may include 1 to 3 heteroatoms.
보다 구체적으로, 치환 또는 비치환된 C6 내지 C30 아릴기는, 치환 또는 비치환된 페닐기, 치환 또는 비치환된 나프틸기, 치환 또는 비치환된 안트라세닐기, 치환 또는 비치환된 페난트레닐기, 치환 또는 비치환된 나프타세닐기, 치환 또는 비치환된 피레닐기, 치환 또는 비치환된 바이페닐기, 치환 또는 비치환된 p-터페닐기, 치환 또는 비치환된 m-터페닐기, 치환 또는 비치환된 o-터페닐기, 치환 또는 비치환된 크리세닐기, 치환 또는 비치환된 벤조페난트레닐기, 치환 또는 비치환된 트리페닐렌기, 치환 또는 비치환된 페릴레닐기, 치환 또는 비치환된 플루오레닐기, 치환 또는 비치환된 인데닐기, 치환 또는 비치환된 퓨라닐기, 또는 이들의 조합일 수 있으나, 이에 제한되지는 않는다.More specifically, a substituted or unsubstituted C6 to C30 aryl group includes a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or Unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted p-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted or unsubstituted o- Terphenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted benzophenanthrenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted perylenyl group, substituted or unsubstituted fluorenyl group, substituted Or an unsubstituted indenyl group, a substituted or unsubstituted furanyl group, or a combination thereof, but is not limited thereto.
보다 구체적으로, 치환 또는 비치환된 C2 내지 C30 헤테로고리기는, 치환 또는 비치환된 티오페닐기, 치환 또는 비치환된 피롤릴기, 치환 또는 비치환된 피라졸릴기, 치환 또는 비치환된 이미다졸일기, 치환 또는 비치환된 트리아졸일기, 치환 또는 비치환된 옥사졸일기, 치환 또는 비치환된 티아졸일기, 치환 또는 비치환된 옥사디아졸일기, 치환 또는 비치환된 티아디아졸일기, 치환 또는 비치환된 피리딜기, 치환 또는 비치환된 피리미디닐기, 치환 또는 비치환된 피라지닐기, 치환 또는 비치환된 트리아지닐기, 치환 또는 비치환된 벤조퓨라닐기, 치환 또는 비치환된 벤조티오페닐기, 치환 또는 비치환된 벤즈이미다졸일기, 치환 또는 비치환된 인돌일기, 치환 또는 비치환된 퀴놀리닐기, 치환 또는 비치환된 이소퀴놀리닐기, 치환 또는 비치환된 퀴나졸리닐기, 치환 또는 비치환된 퀴녹살리닐기, 치환 또는 비치환된 나프티리디닐기, 치환 또는 비치환된 벤즈옥사진일기, 치환 또는 비치환된 벤즈티아진일기, 치환 또는 비치환된 아크리디닐기, 치환 또는 비치환된 페나진일기, 치환 또는 비치환된 페노티아진일기, 치환 또는 비치환된 페녹사진일기, 치환 또는 비치환된 카바졸일기, 치환 또는 비치환된 디벤조퓨란일기, 또는 치환 또는 비치환된 디벤조티오펜일기, 치환 또는 비치환된 벤조나프튜퓨란일기, 치환 또는 비치환된 벤조나프토티오펜일기, 치환 또는 비치환된 벤조퓨라노플루오레닐기, 치환 또는 비치환된 벤조티오펜플루오레닐기 또는 이들의 조합일 수 있으나, 이에 제한되지는 않는다.More specifically, a substituted or unsubstituted C2 to C30 heterocyclic group is a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, A substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted A substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, A substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted benzoxazinyl group, substituted or unsubstituted benzthiazinyl group, substituted or unsubstituted acridinyl group, substituted or unsubstituted phenazine A diyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene a diyl group, a substituted or unsubstituted benzonaphthupuranyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted benzofuranofluorenyl group, a substituted or unsubstituted benzothiophenefluorenyl group, or their It may be a combination, but is not limited thereto.
본 명세서에서, 정공 특성이란, 전기장(electric field)을 가했을 때 전자를 공여하여 정공을 형성할 수 있는 특성을 말하는 것으로, HOMO 준위를 따라 전도 특성을 가져 양극에서 형성된 정공의 발광층으로의 주입, 발광층에서 형성된 정공의 양극으로의 이동 및 발광층에서의 이동을 용이하게 하는 특성을 의미한다. As used herein, the hole property refers to a property capable of forming a hole by donating electrons when an electric field is applied. It refers to a property that facilitates the movement of holes formed in the anode and in the light emitting layer.
또한 전자 특성이란, 전기장을 가했을 때 전자를 받을 수 있는 특성을 말하는 것으로, LUMO 준위를 따라 전도 특성을 가져 음극에서 형성된 전자의 발광층으로의 주입, 발광층에서 형성된 전자의 음극으로의 이동 및 발광층에서의 이동을 용이하게 하는 특성을 의미한다. In addition, the electronic property refers to a property that can receive electrons when an electric field is applied. It has conduction properties along the LUMO level, so electrons formed in the cathode are injected into the light emitting layer, electrons formed in the light emitting layer are moved to the cathode, and in the light emitting layer. properties that facilitate movement.
이하 일 구현예에 따른 유기 광전자 소자용 화합물을 설명한다.Hereinafter, a compound for an organic optoelectronic device according to an embodiment will be described.
일 구현예에 따른 유기 광전자 소자용 화합물은 하기 화학식 1 및 화학식 2의 조합으로 표현된다.The compound for an organic optoelectronic device according to an embodiment is represented by a combination of Chemical Formulas 1 and 2 below.
[화학식 1] [화학식 2][Formula 1] [Formula 2]
상기 화학식 1 및 화학식 2에서,In Formula 1 and Formula 2,
X1은 O 또는 S이고,X 1 is O or S,
L1 내지 L3은 각각 독립적으로 단일 결합 또는 치환 또는 비치환된 C6 내지 C20 아릴렌기이고,L 1 To L 3 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C6 내지 C20 아릴기 또는 치환 또는 비치환된 C2 내지 C30 헤테로고리기이고,Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
a1*, a2*, b1*, b2*, b3* 및 b4*는 각각 독립적으로 연결 탄소 (C) 또는 CRa이고,a1*, a2*, b1*, b2*, b3* and b4* are each independently a linking carbon (C) or CR a ;
a1* 및 a2*는 각각 b1*, b2*, b3* 및 b4* 중 인접한 둘과 연결되고,a 1 * and a 2 * are connected to adjacent two of b 1 *, b 2 *, b 3 * and b 4 *, respectively;
*은 연결 지점이고,* is the connection point,
Ra 및 R1 내지 R3은 각각 독립적으로 수소, 중수소, 할로겐기, 치환 또는 비치환된 C1 내지 C10 알킬기 또는 치환 또는 비치환된 C6 내지 C12 아릴기이고,R a and R 1 to R 3 are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group,
R4 및 R5는 각각 독립적으로 치환 또는 비치환된 C1 내지 C10 알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고,R 4 and R 5 are each independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,
n1은 1 내지 4의 정수 중 하나이고,n1 is one of integers from 1 to 4,
n2는 1 또는 2의 정수이며,n2 is an integer of 1 or 2,
n3은 1 내지 3의 정수 중 하나이다.n3 is one of integers from 1 to 3.
화학식 1 및 화학식 2의 조합으로 표현되는 화합물은 디벤조실롤에 나프토퓨란 (또는 나프토티오펜)이 융합됨으로서 분자의 평면성이 증가되어 격자의 쌓임이 좋아지며 이에 따라 유리 전이 온도 상승 및 정공이동도가 증가된다. 또한, 분자간 쌓임에 참여하지 않는 치환기 (R4 및 R5)로 인해 분자량 대비 높은 유리 전이 온도 및 낮은 증착 공정 온도를 가지며, 아민기가 치환됨으로서 정공 주입 및 정공 이동이 빨라진다.In the compound represented by the combination of Chemical Formulas 1 and 2, naphthofuran (or naphthothiophene) is fused to dibenzosilol, so that the planarity of the molecule is increased, so that the lattice stacking is improved, thereby increasing the glass transition temperature and hole mobility. is increased In addition, due to the substituents (R 4 and R 5 ) that do not participate in intermolecular accumulation, it has a high glass transition temperature and a low deposition process temperature compared to the molecular weight, and the hole injection and hole movement are accelerated as the amine group is substituted.
이러한 구조적 특징에 기인한 높은 유리 전이 온도는 소자 구동 시 발생하는 줄열에 대해서도 안정한 막을 유지하게 하여 안정적인 소자의 특성을 보장하여 우수한 수명을 갖는 소자를 구현할 수 있게 해주며, 낮은 증착 공정 온도는 열증착을 이용한 소자 제작 공정에서의 소자 안정성을 증가시키고, 높은 정공이동도 및 빠른 정공주입특성은 소자의 구동전압을 개선시킨다.The high glass transition temperature due to these structural features maintains a stable film against Joule heat generated during device driving to ensure stable device characteristics and realize devices with excellent lifetime. The device stability is increased in the device manufacturing process using
상기 화학식 1로 표현되는 모이어티는 *이 연결되어 형성하는 나프토의 융합 방향에 따라 하기 화학식 1A 내지 화학식 1C 중 어느 하나로 표현될 수 있다.The moiety represented by Formula 1 may be represented by any one of Formulas 1A to 1C below depending on the fusion direction of naphtho formed by connecting *.
[화학식 1A] [화학식 1B] [화학식 1C][Formula 1A] [Formula 1B] [Formula 1C]
상기 화학식 1A 내지 화학식 1C에서,In Formula 1A to Formula 1C,
X1, R1, R2, n1, n2, a1* 및 a2*는 전술한 바와 같다.X 1 , R 1 , R 2 , n1 , n2 , a1* and a2* are the same as described above.
한편, 상기 화학식 1 및 화학식 2의 조합은 구체적인 조합 위치에 따라 하기 화학식 2A 내지 화학식 2F 중 어느 하나로 표현될 수 있다.Meanwhile, the combination of Chemical Formulas 1 and 2 may be represented by any one of the following Chemical Formulas 2A to 2F according to a specific combination position.
[화학식 2A] [Formula 2A]
[화학식 2B][Formula 2B]
[화학식 2C][Formula 2C]
[화학식 2D][Formula 2D]
[화학식 2E][Formula 2E]
[화학식 2F][Formula 2F]
상기 화학식 2A 내지 화학식 2F 에서,In Formulas 2A to 2F,
X1, L1 내지 L3, Ar1, Ar2 및 R1 내지 R5, 및 n1 내지 n3은 전술한 바와 같고,X 1 , L 1 to L 3 , Ar 1 , Ar 2 and R 1 to R 5 , and n1 to n3 are the same as described above,
Ra1 내지 Ra4는 각각 독립적으로 전술한 Ra의 정의와 같다.R a1 to R a4 are each independently the same as defined above for R a .
일 예로, 상기 화학식 2A는 하기 화학식 2A-A, 화학식 2A-B, 및 화학식 2A-C 중 어느 하나로 표현될 수 있다.For example, Formula 2A may be represented by any one of Formulas 2A-A, Formula 2A-B, and Formula 2A-C.
[화학식 2A-A][Formula 2A-A]
[화학식 2A-B][Formula 2A-B]
[화학식 2A-C][Formula 2A-C]
일 예로, 상기 화학식 2B는 하기 화학식 2B-A, 화학식 2B-B, 및 화학식 2B-C 중 어느 하나로 표현될 수 있다.For example, Chemical Formula 2B may be represented by any one of Chemical Formula 2B-A, Chemical Formula 2B-B, and Chemical Formula 2B-C.
[화학식 2B-A][Formula 2B-A]
[화학식 2B-B][Formula 2B-B]
[화학식 2B-C][Formula 2B-C]
일 예로, 상기 화학식 2C는 하기 화학식 2C-A, 화학식 2C-B, 및 화학식 2C-C 중 어느 하나로 표현될 수 있다.For example, Chemical Formula 2C may be represented by any one of Chemical Formula 2C-A, Chemical Formula 2C-B, and Chemical Formula 2C-C.
[화학식 2C-A][Formula 2C-A]
[화학식 2C-B][Formula 2C-B]
[화학식 2C-C][Formula 2C-C]
일 예로, 상기 화학식 2D는 하기 화학식 2D-A, 화학식 2D-B, 및 화학식 2D-C 중 어느 하나로 표현될 수 있다.For example, Chemical Formula 2D may be represented by any one of Chemical Formula 2D-A, Chemical Formula 2D-B, and Chemical Formula 2D-C.
[화학식 2D-A][Formula 2D-A]
[화학식 2D-B][Formula 2D-B]
[화학식 2D-C][Formula 2D-C]
일 예로, 상기 화학식 2E는 하기 화학식 2E-A, 화학식 2E-B, 및 화학식 2E-C 중 어느 하나로 표현될 수 있다.For example, Formula 2E may be represented by any one of Formulas 2E-A, Formula 2E-B, and Formula 2E-C.
[화학식 2E-A][Formula 2E-A]
[화학식 2E-B][Formula 2E-B]
[화학식 2E-C][Formula 2E-C]
일 예로, 상기 화학식 2F는 하기 화학식 2F-A, 화학식 2F-B, 및 화학식 2F-C 중 어느 하나로 표현될 수 있다.For example, Formula 2F may be represented by any one of Formula 2F-A, Formula 2F-B, and Formula 2F-C.
[화학식 2F-A][Formula 2F-A]
[화학식 2F-B][Formula 2F-B]
[화학식 2F-C][Formula 2F-C]
상기 화학식 2A-A, 화학식 2A-B, 화학식 2A-C, 화학식 2B-A, 화학식 2B-B, 화학식 2B-C, 화학식 2C-A, 화학식 2C-B, 화학식 2C-C, 화학식 2D-A, 화학식 2D-B, 화학식 2D-C, 화학식 2E-A, 화학식 2E-B, 화학식 2E-C, 화학식 2F-A, 화학식 2F-B 및 화학식 2F-C에서, X1, L1 내지 L3, Ar1, Ar2, R1 내지 R5, 및 Ra1 내지 Ra4 및 n1 내지 n3은 전술한 바와 같다.Formula 2A-A, Formula 2A-B, Formula 2A-C, Formula 2B-A, Formula 2B-B, Formula 2B-C, Formula 2C-A, Formula 2C-B, Formula 2C-C, Formula 2D-A , in Formula 2D-B, Formula 2D-C, Formula 2E-A, Formula 2E-B, Formula 2E-C, Formula 2F-A, Formula 2F-B, and Formula 2F-C, X 1 , L 1 to L 3 , Ar 1 , Ar 2 , R 1 to R 5 , and R a1 to R a4 and n1 to n3 are the same as described above.
구체적인 일 예로 상기 화학식 1 및 화학식 2의 조합은 상기 화학식 2C-A, 화학식 2C-B, 화학식 2C-C, 화학식 2F-A, 화학식 2F-B 및 화학식 2F-C 중 어느 하나로 표현될 수 있다.As a specific example, the combination of Formulas 1 and 2 may be represented by any one of Formulas 2C-A, 2C-B, 2C-C, 2F-A, 2F-B, and 2F-C.
상기 화학식 2C-A는 아민기의 구체적인 치환 위치에 따라 예컨대 하기 화학식 2C-A-1, 화학식 2C-A-2, 화학식 2C-A-3, 및 화학식 2C-A-4 중 어느 하나로 표현될 수 있다.Formula 2C-A may be represented by, for example, any one of Formula 2C-A-1, Formula 2C-A-2, Formula 2C-A-3, and Formula 2C-A-4, depending on the specific substitution position of the amine group. have.
[화학식 2C-A-1][Formula 2C-A-1]
[화학식 2C-A-2] [Formula 2C-A-2]
[화학식 2C-A-3][Formula 2C-A-3]
[화학식 2C-A-4][Formula 2C-A-4]
상기 화학식 2C-B는 아민기의 구체적인 치환 위치에 따라 예컨대 하기 화학식 2C-B-1, 화학식 2C-B-2, 화학식 2C-B-3, 및 화학식 2C-B-4 중 어느 하나로 표현될 수 있다.Formula 2C-B may be represented by, for example, any one of Formula 2C-B-1, Formula 2C-B-2, Formula 2C-B-3, and Formula 2C-B-4, depending on the specific substitution position of the amine group. have.
[화학식 2C-B-1][Formula 2C-B-1]
[화학식 2C-B-2][Formula 2C-B-2]
[화학식 2C-B-3][Formula 2C-B-3]
[화학식 2C-B-4][Formula 2C-B-4]
상기 화학식 2C-C는 아민기의 구체적인 치환 위치에 따라 예컨대 하기 화학식 2C-C-1, 화학식 2C-C-2, 화학식 2C-C-3, 및 화학식 2C-C-4 중 어느 하나로 표현될 수 있다.Formula 2C-C may be represented by, for example, any one of the following Formulas 2C-C-1, Formula 2C-C-2, Formula 2C-C-3, and Formula 2C-C-4, depending on the specific substitution position of the amine group. have.
[화학식 2C-C-1][Formula 2C-C-1]
[화학식 2C-C-2][Formula 2C-C-2]
[화학식 2C-C-3][Formula 2C-C-3]
[화학식 2C-C-4][Formula 2C-C-4]
상기 화학식 2F-A는 아민기의 구체적인 치환 위치에 따라 예컨대 하기 화학식 2F-A-1, 화학식 2F-A-2, 화학식 2F-A-3, 및 화학식 2F-A-4 중 어느 하나로 표현될 수 있다.Formula 2F-A may be represented by, for example, any one of Formula 2F-A-1, Formula 2F-A-2, Formula 2F-A-3, and Formula 2F-A-4, depending on the specific substitution position of the amine group. have.
[화학식 2F-A-1][Formula 2F-A-1]
[화학식 2F-A-2][Formula 2F-A-2]
[화학식 2F-A-3][Formula 2F-A-3]
[화학식 2F-A-4][Formula 2F-A-4]
상기 화학식 2F-B는 아민기의 구체적인 치환 위치에 따라 예컨대 하기 화학식 2F-B-1, 화학식 2F-B-2, 화학식 2F-B-3, 및 화학식 2F-B-4 중 어느 하나로 표현될 수 있다.Formula 2F-B may be represented by, for example, any one of Formula 2F-B-1, Formula 2F-B-2, Formula 2F-B-3, and Formula 2F-B-4, depending on the specific substitution position of the amine group. have.
[화학식 2F-B-1][Formula 2F-B-1]
[화학식 2F-B-2][Formula 2F-B-2]
[화학식 2F-B-3][Formula 2F-B-3]
[화학식 2F-B-4][Formula 2F-B-4]
상기 화학식 2F-C는 아민기의 구체적인 치환 위치에 따라 예컨대 하기 화학식 2F-C-1, 화학식 2F-C-2, 화학식 2F-C-3, 및 화학식 2F-C-4 중 어느 하나로 표현될 수 있다.Formula 2F-C may be represented by, for example, any one of Formula 2F-C-1, Formula 2F-C-2, Formula 2F-C-3, and Formula 2F-C-4, depending on the specific substitution position of the amine group. have.
[화학식 2F-C-1][Formula 2F-C-1]
[화학식 2F-C-2][Formula 2F-C-2]
[화학식 2F-C-3][Formula 2F-C-3]
[화학식 2F-C-4][Formula 2F-C-4]
상기 화학식 2C-A-1 내지 화학식 2C-A-4, 화학식 2C-B-1 내지 화학식 2C-B-4, 화학식 2C-C-1 내지 화학식 2C-C-4, 화학식 2F-A-1 내지 화학식 2F-A-4, 화학식 2F-B-1 내지 화학식 2F-B-4 및 화학식 2F-C-1 내지 화학식 2F-C-4에서,Formulas 2C-A-1 to Formula 2C-A-4, Formula 2C-B-1 to Formula 2C-B-4, Formula 2C-C-1 to Formula 2C-C-4, Formula 2F-A-1 to Formula 2C-A-1 to Formula 2C-A-4 In Formulas 2F-A-4, Formulas 2F-B-1 to Formula 2F-B-4, and Formulas 2F-C-1 to Formula 2F-C-4,
X1, L1 내지 L3, Ar1, Ar2, R1 내지 R5, Ra1 내지 Ra4 및 n1 내지 n3은 전술한 바와 같다.X 1 , L 1 to L 3 , Ar 1 , Ar 2 , R 1 to R 5 , R a1 to R a4 and n1 to n3 are the same as described above.
구체적인 일 실시예에서 상기 화학식 1 및 화학식 2의 조합은 상기 화학식 2C-A-2, 화학식 2C-B-2, 화학식 2C-C-2, 화학식 2C-A-3, 화학식 2C-B-3, 화학식 2C-C-3, 화학식 2F-A-2, 화학식 2F-B-2, 화학식 2F-C-2, 화학식 2F-A-3, 화학식 2F-B-3 및 화학식 2F-C-3 중 어느 하나로 표현될 수 있다.In a specific embodiment, the combination of Chemical Formula 1 and Chemical Formula 2 includes Chemical Formula 2C-A-2, Chemical Formula 2C-B-2, Chemical Formula 2C-C-2, Chemical Formula 2C-A-3, Chemical Formula 2C-B-3, Any of Formula 2C-C-3, Formula 2F-A-2, Formula 2F-B-2, Formula 2F-C-2, Formula 2F-A-3, Formula 2F-B-3, or Formula 2F-C-3 can be expressed as one.
일 예로 상기 Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 페닐기, 치환 또는 비치환된 바이페닐기, 치환 또는 비치환된 터페닐기, 치환 또는 비치환된 나프틸기, 치환 또는 비치환된 안트라세닐기, 치환 또는 비치환된 페난트레닐기, 치환 또는 비치환된 크라이세닐기, 치환 또는 비치환된 플루오레닐기, 치환 또는 비치환된 트리페닐렌기, 치환 또는 비치환된 디벤조퓨란일기, 치환 또는 비치환된 디벤조티오펜일기 또는 치환 또는 비치환된 디벤조실롤일기일 수 있다.For example, Ar 1 and Ar 2 are each independently 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 anthracenyl group group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or It may be an unsubstituted dibenzothiophenyl group or a substituted or unsubstituted dibenzosilolyl group.
구체적인 일 예로 상기 Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 페닐기, 치환 또는 비치환된 바이페닐기, 치환 또는 비치환된 나프틸기, 치환 또는 비치환된 플루오레닐기, 치환 또는 비치환된 디벤조퓨란일기, 치환 또는 비치환된 디벤조티오펜일기 또는 치환 또는 비치환된 디벤조실롤일기일 수 있다.In a specific example, Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted It may be a dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.
예컨대 상기 Ar1 및 Ar2는 각각 독립적으로 하기 그룹 Ⅰ에 나열된 치환기 중에서 선택되는 어느 하나일 수 있다.For example, Ar 1 and Ar 2 may each independently be any one selected from the substituents listed in Group I below.
[그룹 Ⅰ][Group I]
상기 그룹 Ⅰ에서,In group I,
D는 중수소를 의미하고,D means deuterium,
n15는 1 내지 5의 정수 중 하나이고,n15 is one of integers from 1 to 5,
n16은 1 내지 7의 정수 중 하나이고,n16 is one of integers from 1 to 7,
n17은 1 내지 3의 정수 중 하나이고,n17 is one of integers from 1 to 3,
n18은 1 내지 4의 정수 중 하나이고,n18 is one of integers from 1 to 4,
*은 연결지점이다.* is the connection point.
일 예로 상기 L1은 단일 결합이고,For example, L 1 is a single bond,
상기 L2 및 L3은 각각 독립적으로 단일 결합 또는 치환 또는 비치환된 페닐렌기일 수 있다.The L 2 and L 3 may each independently be a single bond or a substituted or unsubstituted phenylene group.
일 예로 상기 R1 내지 R3, Ra 및 Ra1 내지 Ra4는 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C1 내지 C5 알킬기 또는 치환 또는 비치환된 C6 내지 C12 아릴기일 수 있다.For example, R 1 to R 3 , R a and R a1 to R a4 may each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.
구체적인 일 예로 상기 R1 내지 R3, Ra 및 Ra1 내지 Ra4는 각각 수소 또는 중수소일 수 있다.In a specific example, R 1 to R 3 , R a and R a1 to R a4 may each be hydrogen or deuterium.
일 예로 상기 R4 및 R5는 각각 독립적으로 치환 또는 비치환된 C1 내지 C5 알킬기 또는 치환 또는 비치환된 C6 내지 C12 아릴기일 수 있다.For example, R 4 and R 5 may each independently represent a substituted or unsubstituted C1 to C5 alkyl group or a substituted or unsubstituted C6 to C12 aryl group.
구체적인 일 예로 상기 R4 및 R5는 각각 독립적으로 치환 또는 비치환된 메틸기, 치환 또는 비치환된 에틸기 또는 치환 또는 비치환된 페닐기일 수 있다.In a specific example, R 4 and R 5 may each independently represent a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, or a substituted or unsubstituted phenyl group.
예컨대 상기 화학식 1 및 화학식 2의 조합으로 표현되는 유기 광전자 소자용 화합물은 하기 그룹 1에 나열된 화합물을 들 수 있으나, 이에 한정되는 것은 아니다.For example, the compound for an organic optoelectronic device represented by a combination of Chemical Formulas 1 and 2 may include compounds listed in Group 1 below, but is not limited thereto.
[그룹 1] [Group 1]
[1-1] [1-2] [1-3] [1-4][1-1] [1-2] [1-3] [1-4]
[1-5] [1-6] [1-7] [1-8][1-5] [1-6] [1-7] [1-8]
[1-9] [1-10] [1-11] [1-12][1-9] [1-10] [1-11] [1-12]
[1-13] [1-14] [1-15] [1-16][1-13] [1-14] [1-15] [1-16]
[1-17] [1-18] [1-19] [1-20][1-17] [1-18] [1-19] [1-20]
[1-21] [1-22] [1-23] [1-24] [1-21] [1-22] [1-23] [1-24]
[1-25] [1-26] [1-27] [1-28] [1-25] [1-26] [1-27] [1-28]
[1-29] [1-30] [1-31] [1-32] [1-29] [1-30] [1-31] [1-32]
[1-33] [1-34] [1-35] [1-36] [1-33] [1-34] [1-35] [1-36]
[1-37] [1-38] [1-39] [1-40] [1-37] [1-38] [1-39] [1-40]
[1-41] [1-42] [1-43] [1-44] [1-41] [1-42] [1-43] [1-44]
[1-45] [1-46] [1-47] [1-48] [1-45] [1-46] [1-47] [1-48]
[1-49] [1-50] [1-51] [1-52] [1-49] [1-50] [1-51] [1-52]
[1-53] [1-54] [1-55] [1-56] [1-53] [1-54] [1-55] [1-56]
[1-57] [1-58] [1-59] [1-60] [1-57] [1-58] [1-59] [1-60]
[1-61] [1-62] [1-63] [1-64] [1-61] [1-62] [1-63] [1-64]
[1-65] [1-66] [1-67] [1-68] [1-65] [1-66] [1-67] [1-68]
[1-69] [1-70] [1-71] [1-72] [1-69] [1-70] [1-71] [1-72]
[1-73] [1-74] [1-75] [1-76] [1-73] [1-74] [1-75] [1-76]
[1-77] [1-78] [1-79] [1-80] [1-77] [1-78] [1-79] [1-80]
[1-81] [1-82] [1-83] [1-84] [1-81] [1-82] [1-83] [1-84]
[1-85] [1-86] [1-87] [1-88] [1-85] [1-86] [1-87] [1-88]
[1-89] [1-90] [1-91] [1-92][1-89] [1-90] [1-91] [1-92]
[1-93] [1-94] [1-95] [1-96][1-93] [1-94] [1-95] [1-96]
[1-97] [1-98] [1-99] [1-100][1-97] [1-98] [1-99] [1-100]
[1-101] [1-102] [1-103] [1-104][1-101] [1-102] [1-103] [1-104]
[1-105] [1-106] [1-107] [1-108][1-105] [1-106] [1-107] [1-108]
[1-109] [1-110] [1-111] [1-112][1-109] [1-110] [1-111] [1-112]
[1-113] [1-114] [1-115] [1-116][1-113] [1-114] [1-115] [1-116]
[1-117] [1-118] [1-119] [1-120][1-117] [1-118] [1-119] [1-120]
[1-121] [1-122] [1-123] [1-124][1-121] [1-122] [1-123] [1-124]
[1-125] [1-126] [1-127] [1-128][1-125] [1-126] [1-127] [1-128]
[1-129] [1-130] [1-131] [1-132][1-129] [1-130] [1-131] [1-132]
[1-133] [1-134] [1-135] [1-136][1-133] [1-134] [1-135] [1-136]
[1-137] [1-138] [1-139] [1-140][1-137] [1-138] [1-139] [1-140]
[1-141] [1-142] [1-143] [1-144][1-141] [1-142] [1-143] [1-144]
[1-145] [1-146] [1-147] [1-148][1-145] [1-146] [1-147] [1-148]
[1-149] [1-150] [1-151] [1-152][1-149] [1-150] [1-151] [1-152]
다른 일 구현예에 따른 유기 광전자 소자용 조성물은 제1 화합물, 및 제2 화합물을 포함하고, 상기 제1 화합물은 전술한 유기 광전자 소자용 화합물이며, 상기 제2 화합물은 하기 화학식 3으로 표현되는 유기 광전자 소자용 화합물일 수 있다.The composition for an organic optoelectronic device according to another exemplary embodiment includes a first compound and a second compound, wherein the first compound is the aforementioned compound for an organic optoelectronic device, and the second compound is an organic compound represented by the following Chemical Formula 3 It may be a compound for an optoelectronic device.
[화학식 3][Formula 3]
상기 화학식 3에서,In Formula 3,
X2는 O, S, N-La-Rb, CRcRd 또는 SiReRf이고,X 2 is O, S, NL a -R b , CR c R d or SiR e R f ,
La는 단일결합, 또는 치환 또는 비치환된 C6 내지 C12 아릴렌기이고,L a is a single bond, or a substituted or unsubstituted C6 to C12 arylene group,
Rb, Rc, Rd, Re, Rf 및 R6은 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C6 내지 C30 아릴기 또는 치환 또는 비치환된 C2 내지 C30 헤테로고리기이고,R b , R c , R d , R e , R f and R 6 are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
n6은 1 내지 4의 정수 중 하나이고,n6 is one of integers from 1 to 4,
A는 하기 그룹 Ⅱ에 나열된 고리 중에서 선택되는 어느 하나이고,A is any one selected from the rings listed in Group II,
[그룹 Ⅱ][Group II]
상기 그룹 Ⅱ에서,In group II,
*은 연결 지점이고,* is the connection point,
X3은 O 또는 S이고,X 3 is O or S,
R7 내지 R14는 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C6 내지 C20 아릴기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로고리기이고,R 7 to R 14 are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
n7, n9, n12 및 n14는 각각 독립적으로 1 내지 4의 정수 중 하나이고,n7, n9, n12 and n14 are each independently an integer of 1 to 4,
n8, n10, n11 및 n13은 각각 독립적으로 1 또는 2의 정수이고,n8, n10, n11 and n13 are each independently an integer of 1 or 2,
Rb 및 R6 내지 R14 중 적어도 하나는 하기 화학식 a로 표현되는 기이고,At least one of R b and R 6 to R 14 is a group represented by the following formula (a),
[화학식 a][Formula a]
상기 화학식 a에서,In the above formula (a),
Z1 내지 Z3은 각각 독립적으로 N 또는 CRg이고,Z 1 to Z 3 are each independently N or CR g ,
Z1 내지 Z3 중 적어도 둘은 N이고,At least two of Z 1 to Z 3 are N,
Rg는 수소, 중수소, 치환 또는 비치환된 C1 내지 C30 알킬기, 또는 치환 또는 비치환된 C6 내지 C30 아릴기이고,R g is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
L4 내지 L6은 각각 독립적으로 단일 결합, 또는 치환 또는 비치환된 C6 내지 C30 아릴렌기이고,L 4 To L 6 are each independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group,
Ar3 및 Ar4는 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로아릴기이고,Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,
*는 연결 지점이다.* is the connection point.
상기 제2 화합물은 질소-함유 6원환으로 치환된 구조를 갖는다.The second compound has a structure substituted with a nitrogen-containing 6-membered ring.
상기 제2 화합물은 질소-함유 6원환으로 치환됨으로써 LUMO 에너지 밴드를 효과적으로 확장시키므로, 전술한 제1 화합물과 함께 발광층에 사용될 경우 전하의 이동성을 높이고 안정성을 높임으로써 정공과 전자의 밸런스를 높여 이를 적용한 소자의 발광 효율 및 수명 특성을 개선시키고 구동 전압을 낮출 수 있다.Since the second compound effectively extends the LUMO energy band by being substituted with a nitrogen-containing 6-membered ring, when used in the light emitting layer together with the above-described first compound, the balance of holes and electrons is increased by increasing the mobility and stability of the charge. It is possible to improve the luminous efficiency and lifespan characteristics of the device and lower the driving voltage.
한편, 상기 제2 화합물의 환 A는 상기 그룹 Ⅱ에 나열된 고리 중에서 선택될 수 있으며, 예컨대 상기 제2 화합물은 하기 화학식 3-Ⅰ 내지 화학식 3-ⅩⅥ 중 어느 하나로 표현될 수 있다.Meanwhile, ring A of the second compound may be selected from the rings listed in Group II, and for example, the second compound may be represented by any one of the following Chemical Formulas 3-I to 3-XVI.
[화학식 3-Ⅰ] [Formula 3-Ⅰ]
상기 화학식 3-Ⅰ에서,In the formula 3-I,
Z1 내지 Z3, R6, R7, L4 내지 L6, Ar3, Ar4, n6 및 n7은 전술한 바와 같다.Z 1 to Z 3 , R 6 , R 7 , L 4 to L 6 , Ar 3 , Ar 4 , n6 and n7 are the same as described above.
[화학식 3-Ⅱ] [화학식 3-Ⅲ][Formula 3-Ⅱ] [Formula 3-Ⅲ]
[화학식 3-Ⅳ] [화학식 3-Ⅴ][Formula 3-IV] [Formula 3-V]
상기 화학식 3-Ⅱ 내지 화학식 3-Ⅴ에서,In the above formulas 3-II to 3-V,
X2, Z1 내지 Z3, R6 내지 R9, L4 내지 L6, Ar3, Ar4, 및 n7 내지 n9는 전술한 바와 같고,X 2 , Z 1 to Z 3 , R 6 to R 9 , L 4 to L 6 , Ar 3 , Ar 4 , and n7 to n9 are the same as described above,
n6은 1 내지 3의 정수 중 하나이다.n6 is one of integers from 1 to 3.
[화학식 3-Ⅵ] [화학식 3-Ⅶ][Formula 3-VI] [Formula 3-VII]
[화학식 3-ⅤⅢ][Formula 3-VIII]
상기 화학식 3-Ⅵ 내지 화학식 3-ⅤⅢ에서,In Formulas 3-VI to 3-VIII,
X2, Z1 내지 Z3, R6, R8, R9, L4 내지 L6, Ar3, Ar4, n6 및 n8은 전술한 바와 같고,X 2 , Z 1 to Z 3 , R 6 , R 8 , R 9 , L 4 to L 6 , Ar 3 , Ar 4 , n6 and n8 are the same as described above,
n9는 1 내지 3의 정수 중 하나이다.n9 is one of integers from 1 to 3.
[화학식 3-Ⅸ] [Formula 3-IX]
상기 화학식 3-Ⅸ에서, In the formula 3-IX,
X2, Z1 내지 Z3, R6, R10 내지 R12, L4 내지 L6, Ar3, Ar4, n6, n10 및 n11은 전술한 바와 같고,X 2 , Z 1 to Z 3 , R 6 , R 10 to R 12 , L 4 to L 6 , Ar 3 , Ar 4 , n6, n10 and n11 are the same as described above,
n12는 1 내지 3의 정수 중 하나이다.n12 is one of integers from 1 to 3.
[화학식 3-Ⅹ][Formula 3-X]
상기 화학식 3-Ⅹ에서, In the formula 3-X,
X2, X3, Z1 내지 Z3, R6, R13, R14, L4 내지 L6, Ar3, Ar4, n13 및 n14는 전술한 바와 같고,X 2 , X 3 , Z 1 to Z 3 , R 6 , R 13 , R 14 , L 4 to L 6 , Ar 3 , Ar 4 , n13 and n14 are the same as described above,
n6은 1 내지 3의 정수 중 하나이다.n6 is one of integers from 1 to 3.
[화학식 3-ⅩⅠ] [화학식 3-ⅩⅡ][Formula 3-XⅠ] [Formula 3-XII]
[화학식 3-ⅩⅢ][Formula 3-XIII]
[화학식 3-ⅩⅣ] [화학식 3-ⅩⅤ][Formula 3-XIV] [Formula 3-XV]
[화학식 3-ⅩⅥ][Formula 3-XVI]
상기 화학식 3-ⅩⅠ 내지 화학식 3-ⅩⅥ에서,In the above formulas 3-XI to 3-XVI,
X2, X3, Z1 내지 Z3, R6, R8 내지 R13, L4 내지 L6, Ar3, Ar4, n6, n9, n10, n12 및 n14는 전술한 바와 같고,X 2 , X 3 , Z 1 to Z 3 , R 6 , R 8 to R 13 , L 4 to L 6 , Ar 3 , Ar 4 , n6, n9, n10, n12 and n14 are the same as described above,
n8, n10 및 n13은 각각 독립적으로 1이다.n8, n10 and n13 are each independently 1;
일 실시예에 따른 제2 화합물은 상기 화학식 3-Ⅱ, 화학식 3-Ⅲ 및 화학식 3-Ⅵ 중 어느 하나로 표현될 수 있다.The second compound according to an embodiment may be represented by any one of Formula 3-II, Formula 3-III, and Formula 3-VI.
구체적인 일 실시예에 따른 제2 화합물은 하기 화학식 3-Ⅱ-3, 화학식 3-Ⅲ-1, 화학식 3-Ⅵ-1 및 하기 화학식 3-Ⅵ-3 중 어느 하나로 표현될 수 있다.The second compound according to a specific embodiment may be represented by any one of Formula 3-II-3, Formula 3-III-1, Formula 3-VI-1, and Formula 3-VI-3 below.
[화학식 3-Ⅱ-3] [화학식 3-Ⅲ-1][Formula 3-Ⅱ-3] [Formula 3-III-1]
[화학식 3-Ⅵ-1] [화학식 3-Ⅵ-3][Formula 3-VI-1] [Formula 3-VI-3]
상기 화학식 3-Ⅱ-3, 화학식 3-Ⅲ-1, 화학식 3-Ⅵ-1 및 하기 화학식 3-Ⅵ-3에서,In Formula 3-II-3, Formula 3-III-1, Formula 3-VI-1, and Formula 3-VI-3,
X2, Z1 내지 Z3, R6 내지 R9, L4 내지 L6, Ar3, Ar4 및 n6 내지 n8은 전술한 바와 같다.X 2 , Z 1 to Z 3 , R 6 to R 9 , L 4 to L 6 , Ar 3 , Ar 4 and n6 to n8 are the same as described above.
일 예로 상기 Ar3 및 Ar4는 각각 독립적으로 치환 또는 비치환된 페닐기, 치환 또는 비치환된 바이페닐기, 치환 또는 비치환된 터페닐기, 치환 또는 비치환된 나프틸기, 치환 또는 비치환된 페난트레닐기, 치환 또는 비치환된 트리페닐렌기, 치환 또는 비치환된 카바졸일기, 치환 또는 비치환된 디벤조퓨란일기, 치환 또는 비치환된 디벤조티오펜일기, 또는 치환 또는 비치환된 디벤조실롤일기일 수 있다.For example, Ar 3 and Ar 4 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenantre Nyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, or substituted or unsubstituted dibenzosilol It could be the weather.
구체적인 일 예로 상기 Ar3 및 Ar4는 각각 독립적으로 치환 또는 비치환된 페닐기, 치환 또는 비치환된 바이페닐기, 또는 치환 또는 비치환된 나프틸기일 수 있다.In a specific example, Ar 3 and Ar 4 may each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.
일 예로 상기 L4 내지 L6은 각각 독립적으로 단일 결합, 치환 또는 비치환된 페닐렌기 또는 치환 또는 비치환된 바이페닐렌기일 수 있다.For example, L 4 to L 6 may each independently represent a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.
구체적인 일 예로 상기 L4 및 L5는 각각 독립적으로 단일 결합 또는 치환 또는 비치환된 페닐렌기이고, 상기 L6은 단일 결합일 수 있다.In a specific example, L 4 and L 5 may each independently represent a single bond or a substituted or unsubstituted phenylene group, and L 6 may be a single bond.
일 예로 상기 R6 내지 R9는 각각 독립적으로 각각 독립적으로 수소, 중수소, 시아노기, 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C6 내지 C12 아릴기, 또는 치환 또는 비치환된 C2 내지 C18 헤테로고리기일 수 있다.For example, R 6 to R 9 are each independently each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a substituted or unsubstituted C2 to C18 heterocyclic group.
구체적인 일 예로 상기 R6 내지 R9는 각각 독립적으로 수소, 중수소, 페닐기, 또는 나프틸기일 수 있다.In a specific example, R 6 to R 9 may each independently be hydrogen, deuterium, a phenyl group, or a naphthyl group.
일 예로 X2는 O, S, CRcRd 또는 SiReRf이고, Rc, Rd, Re 및 Rf는 각각 독립적으로 치환 또는 비치환된 C1 내지 C10 알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기일 수 있다.For example, X 2 is O, S, CR c R d or SiR e R f , and R c , R d , R e and R f are each independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted It may be a C6 to C20 aryl group.
구체적인 일 예로 상기 Rc, Rd, Re 및 Rf는 각각 독립적으로 메틸기, 치환 또는 비치환된 페닐기, 또는 치환 또는 비치환된 바이페닐기일 수 있다.In a specific example, R c , R d , R e and R f may each independently represent a methyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.
예컨대 상기 제2 화합물은 하기 그룹 2에 나열된 화합물에서 선택된 하나일 수 있다.For example, the second compound may be one selected from the compounds listed in Group 2 below.
[그룹 2]
[Group 2]
본 발명의 더욱 구체적인 일 실시예에 따른 유기 광전자 소자용 조성물에는 상기 화학식 2C-A-2, 화학식 2C-A-3, 화학식 2C-B-2, 화학식 2C-C-2, 화학식 2F-A-2, 화학식 2F-A-3, 및 화학식 2F-B-2 중 어느 하나로 표현되는 제1 화합물 및 상기 화학식 3-Ⅲ-1로 표현되는 제2 화합물이 포함될 수 있다.The composition for an organic optoelectronic device according to a more specific embodiment of the present invention includes Chemical Formula 2C-A-2, Chemical Formula 2C-A-3, Chemical Formula 2C-B-2, Chemical Formula 2C-C-2, and Chemical Formula 2F-A- 2, the first compound represented by any one of Formula 2F-A-3, and Formula 2F-B-2, and the second compound represented by Formula 3-III-1 may be included.
제1 화합물과 제2 화합물은 예컨대 1:99 내지 99:1의 중량비로 포함될 수 있다. 상기 범위로 포함됨으로써 제1 화합물의 전자 수송 능력과 제2 화합물의 정공 수송 능력을 이용해 적절한 중량비를 맞추어 바이폴라 특성을 구현하여 효율과 수명을 개선할 수 있다. 상기 범위 내에서 예컨대 약 10:90 내지 90:10, 약 20:80 내지 80:20의 중량비로 포함될 수 있고, 예컨대 약 20:80 내지 약 70: 30, 약 20:80 내지 약 60:40, 그리고 약 30:70 내지 약 60:40의 중량비로 포함될 수 있다. 구체적인 일 예로, 40:60, 50:50, 또는 60:40의 중량비로 포함될 수 있다.The first compound and the second compound may be included, for example, in a weight ratio of 1:99 to 99:1. By being included in the above range, it is possible to implement bipolar characteristics by matching an appropriate weight ratio using the electron transport ability of the first compound and the hole transport ability of the second compound to improve efficiency and lifespan. Within the above range, for example, it may be included in a weight ratio of about 10:90 to 90:10, about 20:80 to 80:20, such as about 20:80 to about 70:30, about 20:80 to about 60:40, And it may be included in a weight ratio of about 30:70 to about 60:40. As a specific example, it may be included in a weight ratio of 40:60, 50:50, or 60:40.
전술한 제1 화합물 및 제2 화합물 외에 1종 이상의 화합물을 더 포함할 수 있다. It may further include one or more compounds in addition to the first compound and the second compound described above.
전술한 유기 광전자 소자용 화합물 또는 유기 광전자 소자용 조성물은 도펀트를 더 포함하는 조성물일 수 있다. The compound for an organic optoelectronic device or the composition for an organic optoelectronic device described above may be a composition further comprising a dopant.
도펀트는 예컨대 인광 도펀트일 수 있고, 예컨대 적색, 녹색 또는 청색의 인광 도펀트일 수 있고, 예컨대 적색 또는 녹색 인광 도펀트일 수 있다.The dopant may be for example a phosphorescent dopant, for example a red, green or blue phosphorescent dopant, for example a red or green phosphorescent dopant.
도펀트는 유기 광전자 소자용 화합물 또는 조성물에 미량 혼합되어 발광을 일으키는 물질로, 일반적으로 삼중항 상태 이상으로 여기시키는 다중항 여기(multiple excitation)에 의해 발광하는 금속 착체(metal complex)와 같은 물질이 사용될 수 있다. 도펀트는 예컨대 무기, 유기, 유무기 화합물일 수 있으며, 1종 또는 2종 이상 포함될 수 있다.A dopant is a material that emits light by being mixed in a small amount in a compound or composition for an organic optoelectronic device. In general, a material such as a metal complex that emits light by multiple excitation excitation to a triplet state or more may be used. can The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may include one or two or more kinds.
도펀트의 일 예로 인광 도펀트를 들 수 있으며, 인광 도펀트의 예로는 Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd 또는 이들의 조합을 포함하는 유기 금속화합물을 들 수 있다. 인광 도펀트는 예컨대 하기 화학식 Z로 표현되는 화합물을 사용할 수 있으나, 이에 한정되는 것은 아니다.An example of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant include Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. and organometallic compounds containing them. The phosphorescent dopant may be, for example, a compound represented by the following Chemical Formula Z, but is not limited thereto.
[화학식 Z][Formula Z]
L7MX4
L 7 MX 4
상기 화학식 Z에서, M은 금속이고, L7 및 X4는 서로 같거나 다르며 M과 착화합물을 형성하는 리간드이다. In Formula Z, M is a metal, and L 7 and X 4 are the same as or different from each other and are ligands forming a complex with M.
상기 M은 예컨대 Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd 또는 이들의 조합일 수 있고, 상기 L7 및 X4는 예컨대 바이덴테이트 리간드일 수 있다.M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or a combination thereof, and L 7 and X 4 are, for example, bi It may be a dentate ligand.
L7 및 X4로 표시되는 리간드의 예로는 하기 그룹 A에 나열된 화학식에서 선택될 수 있으나 이에 한정되는 것은 아니다.Examples of the ligands represented by L 7 and X 4 may be selected from the formulas listed in Group A, but are not limited thereto.
[그룹 A][Group A]
상기 그룹 A에서,In group A,
R300 내지 R302는 각각 독립적으로, 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 C1 내지 C30의 알킬기, C1 내지 C30의 알킬이 치환되거나 치환되지 않은 C6 내지 C30 아릴기 또는 할로겐이고,R 300 to R 302 are each independently hydrogen, deuterium, a halogen substituted or unsubstituted C1 to C30 alkyl group, a C1 to C30 alkyl substituted or unsubstituted C6 to C30 aryl group or halogen,
R303 내지 R324는 각각 독립적으로, 수소, 중수소, 할로겐, 치환 또는 비치환된 C1 내지 C30의 알킬기, 치환 또는 비치환된 C1 내지 C30 알콕시기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 C2 내지 C30의 알케닐기, 치환 또는 비치환된 C6 내지 C30 아릴기, 치환 또는 비치환된 C1 내지 C30 헤테로아릴기, 치환 또는 비치환된 C1 내지 C30 아미노기, 치환 또는 비치환된 C6 내지 C30 아릴아미노기, SF5, 치환 또는 비치환된 C1 내지 C30의 알킬기를 가지는 트리알킬실릴기, 치환 또는 비치환된 C1 내지 C30의 알킬기와 C6 내지 C30의 아릴기를 가지는 디알킬아릴실릴기, 또는 치환 또는 비치환된 C6 내지 C30의 아릴기를 가지는 트리아릴실릴기이다.R 303 to R 324 are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or an unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF 5 , a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or It is a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.
일 예로 하기 화학식 Ⅴ로 표시되는 도펀트를 포함할 수 있다.For example, it may include a dopant represented by the following Chemical Formula V.
[화학식 Ⅴ] [Formula V]
상기 화학식 Ⅴ에서,In the above formula (V),
R101 내지 R116은 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C6 내지 C20 아릴기, 또는 -SiR132R133R134이고,R 101 to R 116 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or —SiR 132 R 133 R 134 ;
상기 R132 내지 R134은 각각 독립적으로 C1 내지 C6 알킬기이고,wherein R 132 to R 134 are each independently a C1 to C6 alkyl group,
R101 내지 R116 중 적어도 하나는 하기 화학식 Ⅴ-1로 표시되는 작용기이고,At least one of R 101 to R 116 is a functional group represented by the following Chemical Formula V-1,
L100은 1가 음이온의 두자리(bidentate) 리간드로, 탄소 또는 헤테로원자의 비공유 전자쌍을 통하여 이리듐에 배위결합하는 리간드이고,L 100 is a bidentate ligand of a monovalent anion, and is a ligand that coordinates to iridium through a lone pair of electrons of carbon or heteroatom,
m1 및 m2은 서로 독립적으로 0 내지 3의 정수 중 어느 하나이고, m1 + m2는 1 내지 3의 정수 중 어느 하나이고,m1 and m2 are each independently any one of an integer of 0 to 3, m1 + m2 is any one of an integer of 1 to 3,
[화학식 Ⅴ-1][Formula V-1]
상기 화학식 Ⅴ-1에서,In Formula V-1,
R135 내지 R139은 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C6 내지 C20 아릴기, 또는 -SiR132R133R134이고,R 135 to R 139 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or —SiR 132 R 133 R 134 ;
*는 탄소 원자와 연결되는 부분을 의미한다.* means a part connected to a carbon atom.
일 예로 하기 화학식 Z-1로 표시되는 도펀트를 포함할 수도 있다.For example, a dopant represented by the following Chemical Formula Z-1 may be included.
[화학식 Z-1][Formula Z-1]
상기 화학식 Z-1에서, 고리 A, B, C, 및 D는 각각 독립적으로 5원 또는 6원 카르보시클릭 또는 헤테로시클릭 고리를 나타내고;In the above formula (Z-1), rings A, B, C, and D each independently represent a 5- or 6-membered carbocyclic or heterocyclic ring;
RA, RB, RC, 및 RD는 각각 독립적으로 일치환, 이치환, 삼치환, 또는 사치환, 또는 비치환을 나타내고;R A , RB , R C , and R D each independently represent mono-, di-, tri-, or tetra-substituted, or unsubstituted;
LB, LC, 및 LD은 각각 직접 결합, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', 및 이의 조합으로 이루어진 군에서 독립적으로 선택되고;L B , L C , and L D are each a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO 2 , CRR′, SiRR′, GeRR′, and combinations thereof independently selected from the group consisting of;
nA이 1인 경우, LE는 직접 결합, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', 및 이의 조합으로 이루어진 군에서 선택되고; nA이 0인 경우, LE는 존재하지 않고;When nA is 1, L E is a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO 2 , CRR', SiRR', GeRR', and combinations thereof. is selected from; when nA is 0, L E is absent;
RA, RB, RC, RD, R, 및 R'은 각각 수소, 중수소, 할로겐, 알킬기, 시클로알킬기, 헤테로알킬기, 아릴알킬기, 알콕시기, 아릴옥시기, 아미노기, 실릴기, 알케닐기, 시클로알케닐기, 헤테로알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아실기, 카르보닐기, 카르복실산기, 에스테르기, 니트릴기, 이소니트릴기, 설파닐기, 설피닐기, 설포닐기, 포스피노기, 및 이의 조합으로 이루어진 군에서 독립적으로 선택되고; 임의의 인접 RA, RB, RC, RD, R, 및 R'은 임의 연결되어 고리를 형성하고; XB, XC, XD, 및 XE는 각각 탄소 및 질소로 이루어진 군에서 독립적으로 선택되고; Q1, Q2, Q3, 및 Q4는 각각 산소 또는 직접 결합을 나타낸다.R A , RB , R C , R D , R , and R' are each hydrogen, deuterium, halogen, an alkyl group, a cycloalkyl group, a heteroalkyl group, an arylalkyl group, an alkoxy group, an aryloxy group, an amino group, a silyl group, an alkenyl group , cycloalkenyl group, heteroalkenyl group, alkynyl group, aryl group, heteroaryl group, acyl group, carbonyl group, carboxylic acid group, ester group, nitrile group, isonitrile group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group independently selected from the group consisting of , and combinations thereof; any adjacent R A , R B , R C , R D , R , and R′ are optionally joined to form a ring; X B , X C , X D , and X E are each independently selected from the group consisting of carbon and nitrogen; Q 1 , Q 2 , Q 3 , and Q 4 each represent oxygen or a direct bond.
일 실시예에 따른 도펀트는 백금 착물일 수 있으며, 예컨대 하기 화학식 Ⅵ로 표현될 수 있다.The dopant according to an embodiment may be a platinum complex, for example, it may be represented by the following Chemical Formula VI.
[화학식 Ⅵ][Formula Ⅵ]
상기 화학식 Ⅵ에서,In the above formula (VI),
X100은 O, S 및 NR131 중에서 선택되고,X 100 is selected from O, S and NR 131 ,
R117 내지 R131은 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C6 내지 C20 아릴기, 또는 - SiR132R133R134이고,R 117 to R 131 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or —SiR 132 R 133 R 134 ;
상기 R132 내지 R134은 각각 독립적으로 C1 내지 C6 알킬기이고,wherein R 132 to R 134 are each independently a C1 to C6 alkyl group,
R117 내지 R131중 적어도 하나는 -SiR132R133R134 또는 tert-부틸기이고,At least one of R 117 to R 131 is -SiR 132 R 133 R 134 or a tert-butyl group,
상기 R132 내지 R134은 각각 독립적으로 C1 내지 C6 알킬기이다.The R 132 to R 134 are each independently a C1 to C6 alkyl group.
이하 상술한 유기 광전자 소자용 화합물 또는 유기 광전자 소자용 조성물을 적용한 유기 광전자 소자를 설명한다.Hereinafter, an organic optoelectronic device to which the above-described compound for an organic optoelectronic device or a composition for an organic optoelectronic device is applied will be described.
유기 광전자 소자는 전기 에너지와 광 에너지를 상호 전환할 수 있는 소자이면 특별히 한정되지 않으며, 예컨대 유기 광전 소자, 유기 발광 소자, 유기 태양 전지 및 유기 감광체 드럼 등을 들 수 있다.The organic optoelectronic device is not particularly limited as long as it is a device capable of converting electrical energy and optical energy, and examples thereof include an organic photoelectric device, an organic light emitting device, an organic solar cell, and an organic photosensitive drum.
여기서는 유기 광전자 소자의 일 예인 유기 발광 소자를 도면을 참고하여 설명한다.Herein, an organic light emitting device, which is an example of an organic optoelectronic device, will be described with reference to the drawings.
도 1은 일 구현예에 따른 유기 발광 소자를 보여주는 단면도이다.1 is a cross-sectional view illustrating an organic light emitting diode according to an exemplary embodiment.
도 1을 참고하면, 일 구현예에 따른 유기 발광 소자 (100)는 서로 마주하는 양극(120)과 음극(110), 그리고 양극(120)과 음극(110) 사이에 위치하는 유기층(105)을 포함한다.Referring to FIG. 1 , an organic light emitting device 100 according to an 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 . include
양극(120)은 예컨대 정공 주입이 원활하도록 일 함수가 높은 도전체로 만들어질 수 있으며, 예컨대 금속, 금속 산화물 및/또는 도전성 고분자로 만들어질 수 있다. 양극(120)은 예컨대 니켈, 백금, 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐주석산화물(ITO), 인듐아연산화물(IZO)과 같은 금속 산화물; ZnO와 Al 또는 SnO2와 Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리(3,4-(에틸렌-1,2-디옥시)티오펜)(polyehtylenedioxythiophene: PEDOT), 폴리피롤 및 폴리아닐린과 같은 도전성 고분자 등을 들 수 있으나, 이에 한정되는 것은 아니다. The anode 120 may be made of, for example, a conductor having a high work function 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 include, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO and Al or SnO 2 and Sb; conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene: PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto. it is not
음극(110)은 예컨대 전자 주입이 원활하도록 일 함수가 낮은 도전체로 만들어질 수 있으며, 예컨대 금속, 금속 산화물 및/또는 도전성 고분자로 만들어질 수 있다. 음극(110)은 예컨대 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 납, 세슘, 바륨 등과 같은 금속 또는 이들의 합금; LiF/Al, LiO2/Al, LiF/Ca, LiF/Al 및 BaF2/Ca과 같은 다층 구조 물질을 들 수 있으나, 이에 한정되는 것은 아니다. The cathode 110 may be made of, for example, a conductor having a low work function to facilitate electron injection, and may be made of, for example, a metal, a metal oxide, and/or a conductive polymer. The negative electrode 110 may include, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; and a multilayer structure material such as LiF/Al, LiO 2 /Al, LiF/Ca, LiF/Al, and BaF 2 /Ca, but is not limited thereto.
유기층(105)은 전술한 유기 광전자 소자용 화합물 또는 유기 광전자 소자용 조성물을 포함할 수 있다. The organic layer 105 may include the aforementioned compound for an organic optoelectronic device or a composition for an organic optoelectronic device.
상기 유기층(105)는 발광층(130)을 포함하고, 발광층(130)은 전술한 유기 광전자 소자용 화합물 또는 유기 광전자 소자용 조성물을 포함할 수 있다. The organic layer 105 may include the emission layer 130 , and the emission layer 130 may include the aforementioned compound for an organic optoelectronic device or a composition for an organic optoelectronic device.
도펀트를 더욱 포함하는 상기 유기 광전자 소자용 조성물은 예컨대 녹색 발광 조성물일 수 있다.The composition for an organic optoelectronic device further comprising a dopant may be, for example, a green light-emitting composition.
발광층(130)은 예컨대 전술한 유기 광전자 소자용 화합물 또는 유기 광전자 소자용 조성물을 각각 인광 호스트로서 포함할 수 있다.The emission layer 130 may include, for example, the above-described compound for an organic optoelectronic device or a composition for an organic optoelectronic device, respectively, as a phosphorescent host.
유기층은 발광층 외에 전하 수송 영역을 더 포함할 수 있다.The organic layer may further include a charge transport region in addition to the emission layer.
상기 전하 수송 영역은 예컨대 정공 수송 영역(140)일 수 있다.The charge transport region may be, for example, the hole transport region 140 .
상기 정공 수송 영역(140)은 양극(120)과 발광층(130) 사이의 정공 주입 및/또는 정공 이동성을 더욱 높이고 전자를 차단할 수 있다.The hole transport region 140 may further increase hole injection and/or hole mobility between the anode 120 and the emission layer 130 and block electrons.
구체적으로 상기 정공 수송 영역(140)은 양극(120)과 발광층(130) 사이의 정공 수송층, 및 상기 발광층(130)과 상기 정공 수송층 사이의 정공 수송 보조층을 포함할 수 있고, 하기 그룹 B에 나열된 화합물 중 적어도 하나는 상기 정공 수송층, 및 정공 수송 보조층 중 적어도 하나의 층에 포함될 수 있다.Specifically, the hole transport region 140 may include a hole transport layer between the anode 120 and the light emitting layer 130 and a hole transport auxiliary layer between the light emitting layer 130 and the hole transport layer. At least one of the listed compounds may be included in at least one of the hole transport layer and the hole transport auxiliary layer.
[그룹 B][Group B]
상기 정공 수송 영역(140)에는 전술한 화합물 외에도 US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A 등에 기재된 공지의 화합물 및 이와 유사한 구조의 화합물도 사용될 수 있다.In the hole transport region 140, in addition to the compounds described above, known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, and the like, and compounds having a similar structure may also be used.
또한, 상기 전하 수송 영역은 예컨대 전자 수송 영역(150)일 수 있다.Also, the charge transport region may be, for example, the electron transport region 150 .
상기 전자 수송 영역(150)은 음극(110)과 발광층(130) 사이의 전자 주입 및/또는 전자 이동성을 더욱 높이고 정공을 차단할 수 있다.The electron transport region 150 may further increase electron injection and/or electron mobility between the cathode 110 and the emission layer 130 and block holes.
구체적으로 상기 전자 수송 영역(150)은 음극(110)과 발광층(130) 사이의 전자 수송층, 및 상기 발광층(130)과 상기 전자 수송층 사이의 전자 수송 보조층을 포함할 수 있고, 하기 그룹 C에 나열된 화합물 중 적어도 하나는 상기 전자 수송층, 및 전자 수송 보조층 중 적어도 하나의 층에 포함될 수 있다.Specifically, the electron transport region 150 may include an electron transport layer between the cathode 110 and the light emitting layer 130 and an electron transport auxiliary layer between the light emitting layer 130 and the electron transport layer. At least one of the listed compounds may be included in at least one of the electron transport layer and the electron transport auxiliary layer.
[그룹 C][Group C]
일 구현예는 유기층으로서 발광층을 포함한 유기 발광 소자일 수 있다.One embodiment may be an organic light emitting device including a light emitting layer as an organic layer.
다른 일 구현예는 유기층으로서 발광층 및 정공 수송 영역을 포함한 유기 발광 소자일 수 있다.Another embodiment may be an organic light emitting device including a light emitting layer and a hole transport region as an organic layer.
또 다른 일 구현예는 유기층으로서 발광층 및 전자 수송 영역을 포함한 유기 발광 소자일 수 있다.Another embodiment may be an organic light emitting device including a light emitting layer and an electron transport region as an organic layer.
본 발명의 일 구현예에 따른 유기 발광 소자는 도 1에서와 같이 유기층(105)으로서 발광층(130) 외에 정공 수송 영역(140) 및 전자 수송 영역(150)을 포함할 수 있다.As shown in FIG. 1 , the organic light emitting device according to an embodiment of the present invention may include a hole transport region 140 and an electron transport region 150 in addition to the emission layer 130 as the organic layer 105 .
한편, 유기 발광 소자는 전술한 유기층으로서 발광층 외에 추가로 전자주입층(미도시), 정공주입층(미도시) 등을 더 포함할 수도 있다. On the other hand, the organic light emitting device may further include an electron injection layer (not shown), a hole injection layer (not shown), etc. in addition to the light emitting layer as the above-described organic layer.
유기 발광 소자(100)는 기판 위에 양극 또는 음극을 형성한 후, 진공증착법(evaporation), 스퍼터링(sputtering), 플라즈마 도금 및 이온도금과 같은 건식성막법 등으로 유기층을 형성한 후, 그 위에 음극 또는 양극을 형성하여 제조할 수 있다.After forming an anode or cathode on a substrate, the organic light emitting device 100 forms an organic layer by a dry film deposition method such as vacuum deposition, sputtering, plasma plating and ion plating, etc., and then a cathode or a It can be manufactured by forming an anode.
상술한 유기 발광 소자는 유기 발광 표시 장치에 적용될 수 있다.The above-described organic light emitting device may be applied to an organic light emitting display device.
이하 실시예를 통하여 상술한 구현예를 보다 상세하게 설명한다. 다만 하기의 실시예는 단지 설명의 목적을 위한 것이며 권리범위를 제한하는 것은 아니다.The above-described embodiment will be described in more detail through the following examples. However, the following examples are for illustrative purposes only and do not limit the scope of rights.
이하, 실시예 및 합성예에서 사용된 출발물질 및 반응물질은 특별한 언급이 없는 한, Sigma-Aldrich 社, TCI 社, tokyo chemical industry에서 구입하였거나, 공지된 방법을 통해 합성하였다.Hereinafter, starting materials and reactants used in Examples and Synthesis Examples were purchased from Sigma-Aldrich, TCI, Tokyo chemical industry, or synthesized through a known method, unless otherwise specified.
(유기 광전자 소자용 화합물의 제조) (Production of compounds for organic optoelectronic devices)
합성예 1: 화합물 1-1의 합성Synthesis Example 1: Synthesis of compound 1-1
[반응식 1][Scheme 1]
1단계: SM-2의 합성Step 1: Synthesis of SM-2
SM-1 (72.15g 275.33mmol)을 tetrahydrofuran(THF) 1 L에 녹인 후, 여기에 2-bromo-4-chloro-1-iodobenzene (62.79 g, 275.33 mmol)와 tetrakis(triphenylphosphine) palladium(9.54 g, 8.26 mmol)을 넣고 교반시켰다. 그리고 물 500ml에 포화된 potassium carbonate(95.13 g, 688.34 mmol)을 넣고 80 ℃에서 12시간 동안 가열하여 환류 시켰다. 반응 완료 후 반응액에 물을 넣고 Ethyl acetate(EA)로 추출한 다음 magnesium sulfate anhydrous로 수분을 제거한 후, 필터하고 감압 농축하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 SM-2을 78.6g (70%)을 얻었다.After dissolving SM-1 (72.15 g 275.33 mmol) in 1 L of tetrahydrofuran (THF), 2-bromo-4-chloro-1-iodobenzene (62.79 g, 275.33 mmol) and tetrakis(triphenylphosphine) palladium (9.54 g, 8.26 mmol) was added and stirred. Then, saturated potassium carbonate (95.13 g, 688.34 mmol) was added to 500 ml of water and heated at 80° C. for 12 hours to reflux. After completion of the reaction, water was added to the reaction solution, extracted with ethyl acetate (EA), water was removed with magnesium sulfate anhydrous, filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain 78.6 g (70%) of SM-2.
2단계: SM-3의 합성Step 2: Synthesis of SM-3
SM-2 (50.4g 192.35mmol)을 tetrahydrofuran(THF) 670 mL에 녹인 후, 내부온도 -78℃에서 n-BuLi (104.5ml g, 261.24 mmol)을 서서히 적가하고 그 온도에서 1시간동안 교반한다. After dissolving SM-2 (50.4 g 192.35 mmol) in 670 mL of tetrahydrofuran (THF), n-BuLi (104.5 ml g, 261.24 mmol) was slowly added dropwise at an internal temperature of -78 ° C and stirred at that temperature for 1 hour.
chlorodimethylsilane (30.64ml, 281.39 mmol)을 -78℃에서 서서히 적가한 후, 상온에서 12시간 교반시켰다. 반응 완료 후 반응액에 물을 넣고 Ethyl acetate(EA)로 추출한 다음 magnesium sulfate anhydrous로 수분을 제거한 후, 필터하고 감압 농축하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 SM-3을 38g (51%)을 얻었다.Chlorodimethylsilane (30.64ml, 281.39 mmol) was slowly added dropwise at -78°C, followed by stirring at room temperature for 12 hours. After completion of the reaction, water was added to the reaction solution, extracted with ethyl acetate (EA), water was removed with magnesium sulfate anhydrous, filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain 38 g (51%) of SM-3.
3단계: SM-4의 합성Step 3: Synthesis of SM-4
SM-3 (38.8g 100.33mmol)을 Trifluoromethylbenzene 300 mL에 녹인 후, di-tert-butyl peroxide (56.42ml g, 300.99 mmol)을 서서히 적가한다. 내부온도 120 ℃에서 48시간 동안 가열하여 환류 시켰다. 반응 종료 후 반응액을 상온으로 식힌 후, 물 200ml를 넣고 1시간 동안 교반한다. Ethyl acetate(EA)로 추출한 다음 magnesium sulfate anhydrous로 수분을 제거한 후, 필터하고 감압 농축하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 SM-4을 21.2g (55%)을 얻었다.After dissolving SM-3 (38.8 g 100.33 mmol) in 300 mL of trifluoromethylbenzene, di-tert-butyl peroxide (56.42 ml g, 300.99 mmol) is slowly added dropwise. It was refluxed by heating at an internal temperature of 120 °C for 48 hours. After completion of the reaction, the reaction solution is cooled to room temperature, 200 ml of water is added, and the mixture is stirred for 1 hour. After extraction with ethyl acetate (EA), moisture was removed with magnesium sulfate anhydrous, filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain 21.2 g (55%) of SM-4.
4단계: 화합물 1-1의 합성Step 4: Synthesis of compound 1-1
SM-4 3.25g (8.42 mmol), SM-5 2.07 g (8.42 mmol), sodium tert-butoxide 2.42 g (25.26 mmol), 및 Tri-tert-butylphosphine 0.34g (0.84 mmol)을 xylenes 50 ml에 용해시키고, Pd2(dba)3 0.38g (0.42 mmol)을 넣은 후 질소 분위기 하에서 12시간 동안 환류 교반 시킨다. 반응 종료 후 xylenes와 증류수로 추출 후 유기층을 무수황산마그네슘으로 건조, 여과하고 여과액을 감압 농축하였다. 생성물을 n-hexane/dichloromethane(2 :1 부피비)으로 실리카겔 컬럼 크로마토그래피로 정제하여 화합물 1-1 3.8g (수율 76%)을 수득 하였다.3.25 g (8.42 mmol) of SM-4, 2.07 g (8.42 mmol) of SM-5, 2.42 g (25.26 mmol) of sodium tert-butoxide, and 0.34 g (0.84 mmol) of Tri-tert-butylphosphine were dissolved in 50 ml of xylenes. , Pd 2 (dba) 3 0.38 g (0.42 mmol) was added and stirred under reflux for 12 hours under a nitrogen atmosphere. After completion of the reaction, extraction was performed with xylenes and distilled water, the organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with n-hexane/dichloromethane (2:1 volume ratio) to obtain 3.8 g of compound 1-1 (yield 76%).
calcd. C42H31NOSi: C, 84.95; H, 5.26; N, 2.36; O, 2.69; Si, 4.73, found: C, 84.95; H, 5.26; N, 2.36; O, 2.69; Si, 4.73calcd. C42H31NOSi: C, 84.95; H, 5.26; N, 2.36; O, 2.69; Si, 4.73, found: C, 84.95; H, 5.26; N, 2.36; O, 2.69; Si, 4.73
합성예 2: 화합물 1-2의 합성Synthesis Example 2: Synthesis of compound 1-2
[반응식 2] [Scheme 2]
상기 합성예 1에서 SM-5 대신 SM-6을 사용한 것을 제외하고, 상기 합성예 1과 동일한 방법으로 상기 반응식 2에 따라 화합물 1-2을 합성하였다.Compound 1-2 was synthesized according to Scheme 2 in the same manner as in Synthesis Example 1, except that SM-6 was used instead of SM-5 in Synthesis Example 1.
calcd. C46H33NOSi: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36, found: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36calcd. C 46 H 33 NOSi: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36, found: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36
합성예 3: 화합물 1-16의 합성 Synthesis Example 3: Synthesis of compound 1-16
[반응식 3][Scheme 3]
상기 합성예 1에서 SM-1 대신 SM-7을 사용하고, SM-5 대신 SM-6을 사용한 것을 제외하고, 상기 합성예 1과 동일한 방법으로 상기 반응식 3에 따라 화합물 1-16을 합성하였다.Compound 1-16 was synthesized according to Scheme 3 in the same manner as in Synthesis Example 1, except that SM-7 was used instead of SM-1 in Synthesis Example 1, and SM-6 was used instead of SM-5.
calcd. C46H33NOSi: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36, found: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36calcd. C 46 H 33 NOSi: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36, found: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36
합성예 4: 화합물 1-27의 합성 Synthesis Example 4: Synthesis of compound 1-27
[반응식 4][Scheme 4]
상기 합성예 1에서 SM-1 대신 SM-11을 사용한 것과 SM-5 대신 SM-15을 사용한 것을 제외하고, 상기 합성예 1과 동일한 방법으로 상기 반응식 4을 따라 화합물 1-27 을 합성하였다.Compound 1-27 was synthesized according to Scheme 4 in the same manner as in Synthesis Example 1, except that SM-11 was used instead of SM-1 in Synthesis Example 1 and SM-15 was used instead of SM-5.
calcd. C46H33NOSi: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36, found: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36calcd. C 46 H 33 NOSi: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36, found: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36
합성예 5: 화합물 1-36의 합성Synthesis Example 5: Synthesis of compound 1-36
[반응식 5][Scheme 5]
상기 합성예 1에서 SM-1 대신 SM-16을 사용하고, SM-5 대신 SM-6을 사용한 것을 제외하고, 상기 합성예 1과 동일한 방법으로 상기 반응식 5에 따라 화합물 1-36을 합성하였다.Compound 1-36 was synthesized according to Scheme 5 in the same manner as in Synthesis Example 1, except that SM-16 was used instead of SM-1 in Synthesis Example 1, and SM-6 was used instead of SM-5.
calcd. C46H33NOSi: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36, found: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36calcd. C 46 H 33 NOSi: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36, found: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36
합성예 6: 화합물 1-48의 합성 Synthesis Example 6: Synthesis of compounds 1-48
[반응식 6][Scheme 6]
상기 합성예 1에서 SM-1 대신 SM-20을 사용하고, SM-5 대신 SM-15을 사용한 것을 제외하고, 상기 합성예 1과 동일한 방법으로 상기 반응식 6에 따라 화합물 1-48을 합성하였다.Compound 1-48 was synthesized according to Scheme 6 in the same manner as in Synthesis Example 1, except that SM-20 was used instead of SM-1 in Synthesis Example 1, and SM-15 was used instead of SM-5.
calcd. C46H33NOSi: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36, found: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36calcd. C 46 H 33 NOSi: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36, found: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36
합성예 7: 화합물 1-57의 합성 Synthesis Example 7: Synthesis of compound 1-57
[반응식 7][Scheme 7]
상기 합성예 1에서 SM-1 대신 SM-24을 사용하고, SM-5 대신 SM-6을 사용한 것을 제외하고, 상기 합성예 1과 동일한 방법으로 상기 반응식 7에 따라 화합물 1-57을 합성하였다.Compound 1-57 was synthesized according to Scheme 7 in the same manner as in Synthesis Example 1, except that SM-24 was used instead of SM-1 in Synthesis Example 1, and SM-6 was used instead of SM-5.
calcd. C46H33NOSi: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36, found: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36calcd. C 46 H 33 NOSi: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36, found: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36
합성예 8: 화합물 1-68의 합성 Synthesis Example 8: Synthesis of compound 1-68
[반응식 8][Scheme 8]
상기 합성예 1에서 SM-1 대신 SM-16을 사용하고, 2-bromo-4-chloro-1-iodobenzene 대신 1-bromo-4-chloro-2-iodobenzene을 사용하며, SM-5 대신 SM-6을 사용한 것을 제외하고, 상기 합성예 1과 동일한 방법으로 상기 반응식 8에 따라 화합물 1-68을 합성하였다.In Synthesis Example 1, SM-16 was used instead of SM-1, 1-bromo-4-chloro-2-iodobenzene was used instead of 2-bromo-4-chloro-1-iodobenzene, and SM-6 was used instead of SM-5. Compound 1-68 was synthesized according to Scheme 8 in the same manner as in Synthesis Example 1, except that .
calcd. C46H33NOSi: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36, found: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36calcd. C 46 H 33 NOSi: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36, found: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36
합성예 9: 화합물 1-98의 합성 Synthesis Example 9: Synthesis of compound 1-98
[반응식 9][Scheme 9]
상기 합성예 1에서 2-bromo-4-chloro-1-iodobenzene 대신 1-bromo-4-chloro-2-iodobenzene을 사용하고, SM-5 대신 SM-6을 사용한 것을 제외하고, 상기 합성예 1과 동일한 방법으로 반응식 9에 따라 화합물 1-98을 합성하였다.In Synthesis Example 1, 1-bromo-4-chloro-2-iodobenzene was used instead of 2-bromo-4-chloro-1-iodobenzene, and SM-6 was used instead of SM-5. Compound 1-98 was synthesized according to Scheme 9 in the same manner.
calcd. C46H33NOSi: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36, found: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36calcd. C 46 H 33 NOSi: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36, found: C, 85.81; H, 5.17; N, 2.18; O, 2.48; Si, 4.36
합성예 10: 화합물 1-135의 합성 Synthesis Example 10: Synthesis of compound 1-135
[반응식 10][Scheme 10]
상기 합성예 1에서 SM-1대신 SM-34를 사용하는 것을 제외하고, 상기 합성예 1과 동일한 방법으로 상기 반응식 10에 따라 화합물 1-135을 합성하였다.Compound 1-135 was synthesized according to Scheme 10 in the same manner as in Synthesis Example 1, except that SM-34 was used instead of SM-1 in Synthesis Example 1.
calcd. C42H31NSSi: C, 82.72; H, 5.12; N, 2.30; S, 5.26; Si, 4.61, found: C, 82.72; H, 5.12; N, 2.30; S, 5.26; Si, 4.61calcd. C 42 H 31 NSSi: C, 82.72; H, 5.12; N, 2.30; S, 5.26; Si, 4.61, found: C, 82.72; H, 5.12; N, 2.30; S, 5.26; Si, 4.61
합성예 11: 화합물 A-3의 합성Synthesis Example 11: Synthesis of compound A-3
[반응식 11][Scheme 11]
1단계: Int-29의 합성Step 1: Synthesis of Int-29
둥근 바닥 플라스크에 2,4-디클로로-6-페닐-1,3,5-트리아진 22.6g (100 mmol)을 테트라하이드로퓨란 200 mL 및 증류수 100 mL에 넣고, 다이벤조퓨란-3-보론산(CAS No.: 395087-89-5) 0.9 당량, 테트라키스트리페닐포스핀 팔라듐 0.03 당량, 탄산칼륨 2 당량을 넣은 후, 질소 대기하에서 가열 환류한다. 6 시간 후 반응액을 냉각시키고, 물층을 제거한 후, 유기층을 감압하에서 건조시킨다. 얻어진 고체를 물과 헥산으로 씻어준 후, 고체를 톨루엔 200 mL로 재결정하여 Int-29를 21.4 g(60% 수율) 얻었다.In a round bottom flask, 22.6 g (100 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine was added to 200 mL of tetrahydrofuran and 100 mL of distilled water, and dibenzofuran-3-boronic acid ( CAS No.: 395087-89-5) 0.9 equivalents, tetrakistriphenylphosphine palladium 0.03 equivalents, and potassium carbonate 2 equivalents are added, and then heated to reflux under nitrogen atmosphere. After 6 hours, the reaction solution was cooled, the water layer was removed, and the organic layer was dried under reduced pressure. After washing the obtained solid with water and hexane, the solid was recrystallized with 200 mL of toluene to obtain 21.4 g (60% yield) of Int-29.
2단계: Int-30의 합성Step 2: Synthesis of Int-30
둥근 바닥 플라스크에 1-Bromo-4-chloro-benzene 50.0 g (261.16 mmol), 2-naphthalene boronic acid 44.9 g (261.16 mmol), 테트라키스트리페닐포스핀 팔라듐 9.1 g (7.83 mmol), 탄산칼륨 71.2 g (522.33 mmol)을 테트라하이드로퓨란 1000 mL 및 증류수 500 mL에 녹인 후 질소 대기하에서 가열 환류한다. 6 시간 후 반응액을 냉각시키고, 물층을 제거한 후, 유기층을 감압하에서 건조시킨다. 얻어진 고체를 물과 헥산으로 씻어준 후, 고체를 톨루엔 200 mL로 재결정하여 Int-30을 55.0 g(88% 수율) 얻었다.In a round bottom flask, 50.0 g (261.16 mmol) of 1-Bromo-4-chloro-benzene, 44.9 g (261.16 mmol) of 2-naphthalene boronic acid, 9.1 g (7.83 mmol) of tetrakistriphenylphosphine palladium, 71.2 g of potassium carbonate (522.33 mmol) was dissolved in 1000 mL of tetrahydrofuran and 500 mL of distilled water, and then heated to reflux under nitrogen atmosphere. After 6 hours, the reaction solution was cooled, the water layer was removed, and the organic layer was dried under reduced pressure. After washing the obtained solid with water and hexane, the solid was recrystallized with 200 mL of toluene to obtain 55.0 g (88% yield) of Int-30.
3단계: Int-31의 합성Step 3: Synthesis of Int-31
둥근 바닥 플라스크에 상기 합성된 Int-30 100.0 g (418.92 mmol)을 DMF 1000 mL에 넣고, 다이클로로다이페닐포스피노페로센 팔라듐 17.1 g (20.95 mmol), 비스피나콜라토 다이보론 127.7 g (502.70 mmol), 초산칼륨 123.3 g (1256.76 mmol)을 넣은 후, 질소 대기하에서 12 시간 동안 가열 환류시켰다. 반응액을 냉각시키고, 물 2 L에 적하시켜 고체를 잡는다. 얻어진 고체를 끓는 톨루엔에 녹여 실리카겔에서 여과한 후 여액을 농축한다. 농축된 고체를 소량의 헥산과 교반 후, 고체를 여과하여 Int-31를 28.5 g(70% 수율) 얻었다.In a round bottom flask, 100.0 g (418.92 mmol) of the synthesized Int-30 was added to 1000 mL of DMF, 17.1 g (20.95 mmol) of dichlorodiphenylphosphinoferrocene palladium, 127.7 g (502.70 mmol) of bispinacolato diboron. , 123.3 g (1256.76 mmol) of potassium acetate was added, and the mixture was heated to reflux under nitrogen atmosphere for 12 hours. The reaction solution is cooled, and the solid is collected by dropping it into 2 L of water. The obtained solid is dissolved in boiling toluene, filtered through silica gel, and the filtrate is concentrated. After the concentrated solid was stirred with a small amount of hexane, the solid was filtered to obtain 28.5 g (70% yield) of Int-31.
4단계: 화합물 A-3의 합성Step 4: Synthesis of Compound A-3
둥근 바닥 플라스크에 Int-31 10.0 g (27.95 mmol), Int-29 11.1 g (33.54 mmol), 테트라키스트리페닐포스핀 팔라듐 1.0 g (0.84 mmol), 및 탄산칼륨 7.7 g (55.90 mmol)을 넣고 테트라하이드로퓨란 150 mL, 증류수 75 mL에 녹인 후 질소 대기하에서 가열 환류한다. 12 시간 후 반응액을 냉각시키고, 물층을 제거한 후, 유기층을 감압하에서 건조시킨다. 얻어진 고체를 물과 메탄올으로 씻어준 후, 고체를 톨루엔 200 mL로 재결정하여 화합물 A-3을 13.4 g(91% 수율) 얻었다.In a round-bottom flask, 10.0 g (27.95 mmol) of Int-31, 11.1 g (33.54 mmol) of Int-29, 1.0 g (0.84 mmol) of tetrakistriphenylphosphine palladium, and 7.7 g (55.90 mmol) of potassium carbonate were placed in a tetra After dissolving in 150 mL of hydrofuran and 75 mL of distilled water, heat to reflux under nitrogen atmosphere. After 12 hours, the reaction solution is cooled, the water layer is removed, and the organic layer is dried under reduced pressure. After washing the obtained solid with water and methanol, the solid was recrystallized with 200 mL of toluene to obtain 13.4 g (91% yield) of Compound A-3.
calcd. C37H23N3O: C, 84.55; H, 4.41; N, 7.99; O, 3.04; found: C, 84.55; H, 4.41; N, 8.00; O, 3.03calcd. C37H23N3O: C, 84.55; H, 4.41; N, 7.99; O, 3.04; found: C, 84.55; H, 4.41; N, 8.00; O, 3.03
합성예 12: 화합물 A-17의 합성Synthesis Example 12: Synthesis of compound A-17
[반응식 12][Scheme 12]
Int-37과 Int-38을 각각 1.0 당량씩 사용하여 상기 합성예 11의 4단계와 같은 방법으로 화합물 A-17을 합성하였다.Compound A-17 was synthesized in the same manner as in step 4 of Synthesis Example 11, using 1.0 equivalents of Int-37 and Int-38, respectively.
calcd. C41H25N3O: C, 85.54; H, 4.38; N, 7.30; O, 2.78; found: C, 85.53; H, 4.38; N, 7.30; O, 2.77calcd. C41H25N3O: C, 85.54; H, 4.38; N, 7.30; O, 2.78; found: C, 85.53; H, 4.38; N, 7.30; O, 2.77
합성예 13: 화합물 A-37의 합성Synthesis Example 13: Synthesis of compound A-37
[반응식 13][Scheme 13]
Int-37과 Int-36를 각각 1.0 당량씩 사용하여 상기 합성예 11의 4단계와 같은 방법으로 화합물 A-37을 합성하였다.Compound A-37 was synthesized in the same manner as in step 4 of Synthesis Example 11, using 1.0 equivalents of Int-37 and Int-36, respectively.
calcd. C37H23N3O: C, 84.55; H, 4.41; N, 7.99; O, 3.04; found: C, 84.57; H, 4.40; N, 7.99; O, 3.03calcd. C37H23N3O: C, 84.55; H, 4.41; N, 7.99; O, 3.04; found: C, 84.57; H, 4.40; N, 7.99; O, 3.03
비교합성예 1: 화합물 C-1의 합성Comparative Synthesis Example 1: Synthesis of Compound C-1
[반응식 14][Scheme 14]
상기 합성예 1에서 SM-1 대신 M-1을 사용한 것을 제외하고, 상기 합성예 1과 동일한 방법으로 상기 반응식 14에 따라 화합물 C-1을 합성하였다.Compound C-1 was synthesized according to Scheme 14 in the same manner as in Synthesis Example 1, except that M-1 was used instead of SM-1 in Synthesis Example 1.
calcd. C38H29NOSi: C, 83.94; H, 5.38; N, 2.58; O, 2.94; Si, 5.17, found: C, 83.94; H, 5.38; N, 2.58; O, 2.94; Si, 5.17calcd. C 38 H 29 NOSi: C, 83.94; H, 5.38; N, 2.58; O, 2.94; Si, 5.17, found: C, 83.94; H, 5.38; N, 2.58; O, 2.94; Si, 5.17
비교합성예 2: 화합물 C-2의 합성Comparative Synthesis Example 2: Synthesis of Compound C-2
[반응식 15][Scheme 15]
상기 합성예 1에서 SM-1 대신 M-5을 사용하고, SM-5의 당량을 M-8에 비하여 2당량을 사용한 것을 제외하고, 상기 합성예 1과 동일한 방법으로 상기 반응식 15에 따라 화합물 C-2를 합성하였다.Compound C according to Scheme 15 in the same manner as in Synthesis Example 1, except that M-5 was used instead of SM-1 in Synthesis Example 1, and 2 equivalents of SM-5 compared to M-8 were used. -2 was synthesized.
calcd. C60H44N2OSi: C, 86.09; H, 5.30; N, 3.35; O, 1.91; Si, 3.35, found: C, 86.09; H, 5.30; N, 3.35; O, 1.91; Si, 3.35calcd. C 60 H 44 N 2 OSi: C, 86.09; H, 5.30; N, 3.35; O, 1.91; Si, 3.35, found: C, 86.09; H, 5.30; N, 3.35; O, 1.91; Si, 3.35
(유기 발광 소자의 제작) (Production of organic light emitting device)
실시예 1Example 1
ITO (Indium tin oxide)로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 이송시킨 다음 산소 플라즈마를 이용하여 상기 기판을 10분간 세정 한 후 진공 증착기로 기판을 이송하였다. 이렇게 준비된 ITO 투명 전극을 양극으로 사용하여 ITO 기판 상부에 3 % NDP-9 (Novaled社로부터 시판됨)으로 도핑된 화합물 A를 진공 증착하여 100Å 두께의 정공주입층을 형성하고, 상기 정공주입층의 상부에 화합물 A를 1300Å의 두께로 증착하여 정공수송층을 형성하였다. 상기 정공수송층 상부에 화합물 B를 700Å의 두께로 증착하여 정공수송보조층을 형성하였다. 정공수송보조층 상부에 합성예 1에서 얻어진 화합물 1-1을 호스트로 사용하고 도판트로 [Ir(piq)2acac]를 2wt% 로 도핑하여 진공 증착으로 400Å 두께의 발광층을 형성하였다. 이어서 상기 발광층 상부에 화합물 C를 50Å의 두께로 증착하여 전자수송보조층을 형성하고, 화합물 D와 LiQ를 동시에 1:1의 중량비로 진공 증착하여 300 Å 두께의 전자수송층을 형성하였다. 상기 전자수송층 상부에 LiQ 15Å과 Al 1200Å을 순차적으로 진공 증착 하여 음극을 형성함으로써 유기발광소자를 제작하였다.A glass substrate coated with a thin film of ITO (Indium tin oxide) was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning was performed with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a plasma cleaner. After cleaning the substrate using oxygen plasma for 10 minutes, the substrate was transferred to a vacuum evaporator. Using the prepared ITO transparent electrode as an anode, compound A doped with 3% NDP-9 (commercially available from Novaled) was vacuum-deposited on the top of the ITO substrate to form a hole injection layer with a thickness of 100 Å, and Compound A was deposited thereon to a thickness of 1300 Å to form a hole transport layer. Compound B was deposited on the hole transport layer to a thickness of 700 Å to form a hole transport auxiliary layer. Compound 1-1 obtained in Synthesis Example 1 was used as a host on the hole transport auxiliary layer, and [Ir(piq) 2 acac] was doped at 2 wt% as a dopant to form an emission layer with a thickness of 400 Å by vacuum deposition. Subsequently, compound C was deposited on the light emitting layer to a thickness of 50 Å to form an electron transport auxiliary layer, and compound D and LiQ were simultaneously vacuum deposited at a weight ratio of 1:1 to form an electron transport layer having a thickness of 300 Å. An organic light emitting diode was manufactured by sequentially vacuum-depositing 15 Å of LiQ and 1200 Å of Al on the electron transport layer to form a cathode.
ITO / 화합물A (3 % NDP-9 doping, 100Å) / 화합물A (1300Å) / 화합물B (700Å) / EML [화합물 1-1 (98wt%), [Ir(piq)2acac] (2wt%)] (400Å) / 화합물C (50Å) / 화합물D : Liq(300Å) / LiQ (15Å) / Al (1200Å)의 구조로 제작하였다.ITO / Compound A (3% NDP-9 doping, 100Å) / Compound A (1300Å) / Compound B (700Å) / EML [Compound 1-1 (98wt%), [Ir(piq) 2 acac] (2wt%) ] (400 Å) / Compound C (50 Å) / Compound D: Liq (300 Å) / LiQ (15 Å) / Al (1200 Å).
화합물 A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amineCompound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine
화합물 B: N,N-di([1,1'-biphenyl]-4-yl)-7,7-dimethyl-7H-fluoreno[4,3-b]benzofuran-10-amineCompound B: N,N-di([1,1'-biphenyl]-4-yl)-7,7-dimethyl-7H-fluoreno[4,3-b]benzofuran-10-amine
화합물 C: 2-(3-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)phenyl)-4,6-diphenyl-1,3,5-triazineCompound C: 2-(3-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)phenyl)-4,6-diphenyl-1,3,5-triazine
화합물 D: 8-(4-(4,6-di(naphthalen-2-yl)-1,3,5-triazin-2-yl)phenyl)quinolineCompound D: 8-(4-(4,6-di(naphthalen-2-yl)-1,3,5-triazin-2-yl)phenyl)quinoline
실시예 2 내지 18, 비교예 1 및 2Examples 2 to 18, Comparative Examples 1 and 2
하기 표 1에 기재한 바와 같이 호스트로 변경한 것을 제외하고, 상기 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that the host was changed as shown in Table 1 below.
실시예 19Example 19
ITO (Indium tin oxide)로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 이송시킨 다음 산소 플라즈마를 이용하여 상기 기판을 10분간 세정한 후 진공 증착기로 기판을 이송하였다. 이렇게 준비된 ITO 투명 전극을 양극으로 사용하여 ITO 기판 상부에 3 % NDP-9 (Novaled社로부터 시판됨)으로 도핑된 화합물 A를 진공 증착하여 100Å 두께의 정공주입층을 형성하고, 상기 정공주입층의 상부에 화합물 A를 1300Å의 두께로 증착하여 정공수송층을 형성하였다. 상기 정공수송층 상부에 화합물 B를 700Å의 두께로 증착하여 정공수송보조층을 형성하였다. 정공수송층 상부에 합성예 1에서 얻어진 화합물 1-1 및 합성예 12에서 얻어진 화합물 A-17을 호스트로 동시에 사용하고 도판트로 [Ir(piq)2acac]를 2wt%로 도핑하여 진공 증착으로 400Å 두께의 발광층을 형성하였다. 여기서 화합물 1-1 및 화합물 A-17은 5:5의 중량비로 사용되었다. 이어서 상기 발광층 상부에 화합물 C를 50Å의 두께로 증착하여 전자수송보조층을 형성하고, 화합물 D와 LiQ를 동시에 1:1의 중량비로 진공 증착하여 300 Å 두께의 전자수송층을 형성하였다. 상기 전자수송층 상부에 LiQ 15Å과 Al 1200Å을 순차적으로 진공 증착 하여 음극을 형성함으로써 유기발광소자를 제작하였다.A glass substrate coated with a thin film of ITO (Indium tin oxide) was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning was performed with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, and transferred to a plasma cleaner. After cleaning the substrate for 10 minutes using oxygen plasma, the substrate was transferred to a vacuum evaporator. Using the prepared ITO transparent electrode as an anode, compound A doped with 3% NDP-9 (commercially available from Novaled) was vacuum-deposited on the top of the ITO substrate to form a hole injection layer with a thickness of 100 Å, and Compound A was deposited thereon to a thickness of 1300 Å to form a hole transport layer. Compound B was deposited on the hole transport layer to a thickness of 700 Å to form a hole transport auxiliary layer. Compound 1-1 obtained in Synthesis Example 1 and compound A-17 obtained in Synthesis Example 12 were simultaneously used as a host on the hole transport layer, and doped with [Ir(piq) 2 acac] as a dopant at 2 wt% to a thickness of 400 Å by vacuum deposition. of the light emitting layer was formed. Here, Compound 1-1 and Compound A-17 were used in a weight ratio of 5:5. Subsequently, compound C was deposited on the light emitting layer to a thickness of 50 Å to form an electron transport auxiliary layer, and compound D and LiQ were simultaneously vacuum deposited at a weight ratio of 1:1 to form an electron transport layer having a thickness of 300 Å. An organic light emitting diode was manufactured by sequentially vacuum-depositing 15 Å of LiQ and 1200 Å of Al on the electron transport layer to form a cathode.
ITO / 화합물A (3 % NDP-9 doping, 100Å) / 화합물A (1300Å) / 화합물B (700Å) / EML [화합물 1-1 : 화합물 A-17 : [Ir(piq)2acac] = 49wt% : 49wt% : (2wt%)] (400Å) / 화합물C (50Å) / 화합물D : Liq(300Å) / LiQ (15Å) / Al (1200Å)의 구조로 제작하였다.ITO / Compound A (3% NDP-9 doping, 100Å) / Compound A (1300Å) / Compound B (700Å) / EML [Compound 1-1: Compound A-17: [Ir(piq) 2 acac] = 49wt% : 49wt%: (2wt%)] (400Å) / Compound C (50Å) / Compound D: Liq (300Å) / LiQ (15Å) / Al (1200Å) was prepared.
실시예 20 내지 29, 및 비교예 3 내지 6Examples 20 to 29, and Comparative Examples 3 to 6
하기 표 2에 기재한 바와 같이 호스트를 변경한 것을 제외하고는, 상기 실시예 19와 동일한 방법으로 유기발광소자를 제작하였다.An organic light emitting diode was manufactured in the same manner as in Example 19, except that the host was changed as shown in Table 2 below.
평가evaluation
실시예 1 내지 29와 비교예 1 내지 6에 따른 유기발광소자의 발광효율 및 수명특성을 평가하였다. The luminous efficiency and lifespan characteristics of the organic light emitting diodes according to Examples 1 to 29 and Comparative Examples 1 to 6 were evaluated.
구체적인 측정방법은 하기와 같고, 그 결과는 표 1 및 표 2와 같다.Specific measurement methods are as follows, and the results are shown in Tables 1 and 2.
(1) 전압변화에 따른 전류밀도의 변화 측정(1) Measurement of change in current density according to voltage change
제조된 유기발광소자에 대해, 전압을 0V 부터 10V까지 상승시키면서 전류-전압계(Keithley 2400)를 이용하여 단위소자에 흐르는 전류값을 측정하고, 측정된 전류값을 면적으로 나누어 결과를 얻었다.For the manufactured organic light emitting device, the current flowing through the unit device was measured using a current-voltmeter (Keithley 2400) while the voltage was increased from 0V to 10V, and the measured current value was divided by the area to obtain a result.
(2) 전압변화에 따른 휘도변화 측정(2) Measurement of luminance change according to voltage change
제조된 유기발광소자에 대해, 전압을 0V 부터 10V까지 상승시키면서 휘도계(Minolta Cs-1000A)를 이용하여 그 때의 휘도를 측정하여 결과를 얻었다. For the manufactured organic light emitting device, the luminance was measured at that time using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0V to 10V, and results were obtained.
(3) 발광효율 측정(3) Measurement of luminous efficiency
상기(1) 및 (2)로부터 측정된 휘도와 전류밀도 및 전압을 이용하여 동일 전류밀도(10 mA/cm2)의 발광효율(cd/A)을 계산하였다.The luminous efficiency (cd/A) of the same current density (10 mA/cm 2 ) was calculated using the luminance, current density, and voltage measured from (1) and (2) above.
비교예 1의 발광효율을 기준으로 한 상대 값을 계산하여 하기 표 1에 나타내었다.The relative values based on the luminous efficiency of Comparative Example 1 were calculated and shown in Table 1 below.
비교예 3의 발광효율을 기준으로 한 상대 값을 계산하여 하기 표 2에 나타내었다.The relative values based on the luminous efficiency of Comparative Example 3 were calculated and shown in Table 2 below.
(4) 수명 측정(4) Lifetime measurement
제조된 유기발광소자에 대해 폴라로닉스 수명측정 시스템을 사용하여 실시예 1 내지 29, 및 비교예 1 내지 6의 소자를 초기휘도(cd/m2)를 6,000cd/m2로 발광시키고 시간경과에 따른 휘도의 감소를 측정하여 초기 휘도 대비 95%로 휘도가 감소된 시점을 T95 수명으로 측정하였다.For the prepared organic light emitting device, the devices of Examples 1 to 29, and Comparative Examples 1 to 6 using a polaronics lifetime measurement system emit light with an initial luminance (cd/m 2 ) of 6,000 cd/m 2 , and in time The time when the luminance decreased to 95% compared to the initial luminance was measured as the T95 lifetime by measuring the decrease in luminance.
비교예 1의 T95 수명을 기준으로 한 상대 값을 계산하여 하기 표 1에 나타내었다.The relative values based on the T95 lifetime of Comparative Example 1 were calculated and shown in Table 1 below.
비교예 3의 T95 수명을 기준으로 한 상대 값을 계산하여 하기 표 2에 나타내었다.The relative values based on the T95 lifetime of Comparative Example 3 were calculated and shown in Table 2 below.
| 구분division | 호스트host | 효율(%)efficiency(%) | T95 수명(%)T95 life (%) |
| 실시예 1Example 1 | 1-11-1 | 112 112 | 109 109 |
| 실시예 2Example 2 | 1-21-2 | 114 114 | 120 120 |
| 실시예 3Example 3 | 1-61-6 | 116 116 | 116 116 |
| 실시예 4Example 4 | 1-171-17 | 111 111 | 110 110 |
| 실시예 5Example 5 | 1-211-21 | 110 110 | 114 114 |
| 실시예 6Example 6 | 1-271-27 | 110 110 | 106 106 |
| 실시예 7Example 7 | 1-291-29 | 109 109 | 108 108 |
| 실시예 8Example 8 | 1-351-35 | 118 118 | 118 118 |
| 실시예 9Example 9 | 1-361-36 | 117 117 | 122 122 |
| 실시예 10Example 10 | 1-471-47 | 109 109 | 110 110 |
| 실시예 11Example 11 | 1-511-51 | 108 108 | 108 108 |
| 실시예 12Example 12 | 1-571-57 | 105 105 | 109 109 |
| 실시예 13Example 13 | 1-681-68 | 110 110 | 106 106 |
| 실시예 14Example 14 | 1-1011-101 | 112 112 | 110 110 |
| 실시예 15Example 15 | 1-1211-121 | 110 110 | 108 108 |
| 실시예 16Example 16 | 1-1271-127 | 113 113 | 108 108 |
| 실시예 17Example 17 | 1-1361-136 | 109 109 | 107 107 |
| 실시예 18Example 18 | 1-1421-142 | 112 112 | 109 109 |
| 비교예 1Comparative Example 1 | C-1C-1 | 100 100 | 100 100 |
| 비교예 2Comparative Example 2 | C-2C-2 | 91 91 | 40 40 |
| 구분division | 호스트host | 효율(%)efficiency(%) | T95 수명(%)T95 Life (%) | |
|
제1 호스트first host |
제2 호스트second host |
|||
| 실시예 19Example 19 | 1-11-1 | A-17A-17 | 110 110 | 110110 |
| 실시예 20Example 20 | 1-61-6 | A-17A-17 | 109 109 | 107 107 |
| 실시예 21Example 21 | 1-171-17 | A-17A-17 | 108 108 | 105105 |
| 실시예 22Example 22 | 1-361-36 | A-17A-17 | 113 113 | 104 104 |
| 실시예 23Example 23 | 1-471-47 | A-17A-17 | 110 110 | 110110 |
| 실시예 24Example 24 | 1-1211-121 | A-17A-17 | 112 112 | 105 105 |
| 실시예 25Example 25 | 1-1271-127 | A-17A-17 | 114 114 | 104104 |
| 실시예 26Example 26 | 1-1361-136 | A-17A-17 | 109 109 | 109109 |
| 실시예 27Example 27 | 1-61-6 | A-37A-37 | 110 110 | 104 104 |
| 실시예 28Example 28 | 1-361-36 | A-37A-37 | 112 112 | 110110 |
| 실시예 29Example 29 | 1-1211-121 | A-37A-37 | 111 111 | 103103 |
| 비교예 3Comparative Example 3 | C-1C-1 | A-17A-17 | 100 100 | 100100 |
| 비교예 4Comparative Example 4 | C-2C-2 | A-17A-17 | 90 90 | 36 36 |
| 비교예 5Comparative Example 5 | C-1C-1 | A-37A-37 | 100 100 | 9999 |
| 비교예 6Comparative Example 6 | C-2C-2 | A-37A-37 | 91 91 | 43 43 |
표 1을 참고하면, 본 발명에 따른 화합물은 비교 화합물 대비 단독호스트에서 효율과 수명이 개선된 것을 확인할 수 있었고, 특히 표 2를 참고하면, 제2 호스트와 조합을 하였을 때 효율, 수명이 전체적으로 크게 개선된 것을 확인할 수 있다.Referring to Table 1, it was confirmed that the compound according to the present invention has improved efficiency and lifespan in a single host compared to the comparative compound. improvement can be seen.
실시예들에 대하여 상세하게 설명하였지만 본 발명의 권리범위는 이에 한정되는 것은 아니고 다음의 청구 범위에서 정의하고 있는 본 발명의 기본 개념을 이용한 당업자의 여러 변형 및 개량 형태 또한 본 발명의 권리범위에 속하는 것이다. Although the embodiments have been described in detail, the scope of the present invention is not limited thereto, and various modifications and improvements by those skilled in the art using the basic concept of the present invention defined in the following claims also fall within the scope of the present invention. will be.
Claims (18)
- 하기 화학식 1 및 화학식 2의 조합으로 표현되는 유기 광전자 소자용 화합물:A compound for an organic optoelectronic device represented by a combination of Formula 1 and Formula 2 below:[화학식 1] [화학식 2][Formula 1] [Formula 2]
상기 화학식 1 및 화학식 2에서,In Formula 1 and Formula 2,X1은 O 또는 S이고,X 1 is O or S,L1 내지 L3은 각각 독립적으로 단일 결합 또는 치환 또는 비치환된 C6 내지 C20 아릴렌기이고,L 1 To L 3 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C6 내지 C20 아릴기 또는 치환 또는 비치환된 C2 내지 C30 헤테로고리기이고,Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,a1*, a2*, b1*, b2*, b3* 및 b4*는 각각 독립적으로 연결 탄소 (C) 또는 CRa이고,a1*, a2*, b1*, b2*, b3* and b4* are each independently a linking carbon (C) or CR a ;a1* 및 a2*는 각각 b1*, b2*, b3* 및 b4* 중 인접한 둘과 연결되고,a 1 * and a 2 * are connected to adjacent two of b 1 *, b 2 *, b 3 * and b 4 *, respectively;*은 연결 지점이고,* is the connection point,Ra 및 R1 내지 R3은 각각 독립적으로 수소, 중수소, 할로겐기, 치환 또는 비치환된 C1 내지 C10 알킬기 또는 치환 또는 비치환된 C6 내지 C12 아릴기이고,R a and R 1 to R 3 are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group,R4 및 R5는 각각 독립적으로 치환 또는 비치환된 C1 내지 C10 알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고,R 4 and R 5 are each independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,n1은 1 내지 4의 정수 중 하나이고,n1 is one of integers from 1 to 4,n2는 1 또는 2의 정수이며,n2 is an integer of 1 or 2,n3은 1 내지 3의 정수 중 하나이다.n3 is one of integers from 1 to 3. - 제1항에서, In claim 1,상기 화학식 1은 하기 화학식 1A 내지 화학식 1C 중 어느 하나로 표현되는 유기 광전자 소자용 화합물:Formula 1 is a compound for an organic optoelectronic device represented by any one of Formula 1A to Formula 1C:[화학식 1A] [화학식 1B] [화학식 1C][Formula 1A] [Formula 1B] [Formula 1C]
상기 화학식 1A 내지 화학식 1C에서,In Formula 1A to Formula 1C,X1, R1, R2, n1, n2, a1* 및 a2*는 제1항에서 정의한 바와 같다.X 1 , R 1 , R 2 , n1, n2, a1* and a2* are as defined in claim 1. - 제1항에서, In claim 1,상기 화학식 1 및 화학식 2의 조합은 하기 화학식 2A 내지 화학식 2F 중 어느 하나로 표현되는 것인, 유기 광전자 소자용 화합물:The combination of Formula 1 and Formula 2 is represented by any one of Formulas 2A to 2F below, a compound for an organic optoelectronic device:[화학식 2A] [Formula 2A]
[화학식 2B][Formula 2B]
[화학식 2C][Formula 2C]
[화학식 2D][Formula 2D]
[화학식 2E][Formula 2E]
[화학식 2F][Formula 2F]
상기 화학식 2A 내지 화학식 2F 에서,In Formulas 2A to 2F,X1, L1 내지 L3, Ar1, Ar2 및 R1 내지 R5, 및 n1 내지 n3은 제1항에서 정의한 바와 같고,X 1 , L 1 to L 3 , Ar 1 , Ar 2 and R 1 to R 5 , and n1 to n3 are as defined in claim 1 ,Ra1 내지 Ra4는 각각 독립적으로 제1항에서 정의한 Ra와 같다.R a1 to R a4 are each independently the same as R a defined in claim 1 . - 제1항에 있어서,According to claim 1,상기 화학식 1 및 화학식 2의 조합은 하기 화학식 2C-A, 화학식 2C-B, 화학식 2C-C, 화학식 2F-A, 화학식 2F-B 및 화학식 2F-C 중 어느 하나로 표현되는 유기 광전자 소자용 화합물:The combination of Formula 1 and Formula 2 is a compound for an organic optoelectronic device represented by any one of Formula 2C-A, Formula 2C-B, Formula 2C-C, Formula 2F-A, Formula 2F-B, and Formula 2F-C:[화학식 2C-A][Formula 2C-A]
[화학식 2C-B][Formula 2C-B]
[화학식 2C-C][Formula 2C-C]
[화학식 2F-A][Formula 2F-A]
[화학식 2F-B][Formula 2F-B]
[화학식 2F-C][Formula 2F-C]
상기 화학식 2C-A, 화학식 2C-B, 화학식 2C-C, 화학식 2F-A, 화학식 2F-B 및 화학식 2F-C에서,In Formula 2C-A, Formula 2C-B, Formula 2C-C, Formula 2F-A, Formula 2F-B and Formula 2F-C,X1, L1 내지 L3, Ar1, Ar2 및 R1 내지 R5 및 n1 내지 n3은 제1항에서 정의한 바와 같고,X 1 , L 1 to L 3 , Ar 1 , Ar 2 and R 1 to R 5 and n1 to n3 are as defined in claim 1,Ra1 내지 Ra4는 각각 독립적으로 제1항에서 정의한 Ra와 같다.R a1 to R a4 are each independently the same as R a defined in claim 1 . - 제4항에 있어서,5. The method of claim 4,하기 화학식 2C-A-2, 화학식 2C-B-2, 화학식 2C-C-2, 화학식 2C-A-3, 화학식 2C-B-3, 화학식 2C-C-3, 화학식 2F-A-2, 화학식 2F-B-2, 화학식 2F-C-2, 화학식 2F-A-3, 화학식 2F-B-3 및 화학식 2F-C-3 중 어느 하나로 표현되는 유기 광전자 소자용 화합물:Formula 2C-A-2, Formula 2C-B-2, Formula 2C-C-2, Formula 2C-A-3, Formula 2C-B-3, Formula 2C-C-3, Formula 2F-A-2, A compound for an organic optoelectronic device represented by any one of Formula 2F-B-2, Formula 2F-C-2, Formula 2F-A-3, Formula 2F-B-3, and Formula 2F-C-3:[화학식 2C-A-2][Formula 2C-A-2]
[화학식 2C-B-2][Formula 2C-B-2]
[화학식 2C-C-2][Formula 2C-C-2]
[화학식 2C-A-3][Formula 2C-A-3]
[화학식 2C-B-3][Formula 2C-B-3]
[화학식 2C-C-3][Formula 2C-C-3]
[화학식 2F-A-2][Formula 2F-A-2]
[화학식 2F-B-2][Formula 2F-B-2]
[화학식 2F-C-2][Formula 2F-C-2]
[화학식 2F-A-3][Formula 2F-A-3]
[화학식 2F-B-3][Formula 2F-B-3]
[화학식 2F-C-3][Formula 2F-C-3]
화학식 2C-A-2, 화학식 2C-B-2, 화학식 2C-C-2, 화학식 2C-A-3, 화학식 2C-B-3, 화학식 2C-C-3, 화학식 2F-A-2, 화학식 2F-B-2, 화학식 2F-C-2, 화학식 2F-A-3, 화학식 2F-B-3 및 화학식 2F-C-3에서,Formula 2C-A-2, Formula 2C-B-2, Formula 2C-C-2, Formula 2C-A-3, Formula 2C-B-3, Formula 2C-C-3, Formula 2F-A-2, Formula In 2F-B-2, Formula 2F-C-2, Formula 2F-A-3, Formula 2F-B-3 and Formula 2F-C-3,X1, L1 내지 L3, Ar1, Ar2, R1 내지 R5, 및 Ra1 내지 Ra4및 n1 내지 n3은 제4항에서 정의한 바와 같다.X 1 , L 1 to L 3 , Ar 1 , Ar 2 , R 1 to R 5 , and R a1 to R a4 and n1 to n3 are as defined in claim 4 . - 제1항에 있어서,According to claim 1,상기 Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 페닐기, 치환 또는 비치환된 바이페닐기, 치환 또는 비치환된 터페닐기, 치환 또는 비치환된 나프틸기, 치환 또는 비치환된 안트라세닐기, 치환 또는 비치환된 페난트레닐기, 치환 또는 비치환된 크라이세닐기, 치환 또는 비치환된 플루오레닐기, 치환 또는 비치환된 트리페닐렌기, 치환 또는 비치환된 디벤조퓨란일기, 치환 또는 비치환된 디벤조티오펜일기 또는 치환 또는 비치환된 디벤조실롤일기인, 유기 광전자 소자용 화합물.wherein Ar 1 and Ar 2 are each independently 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 anthracenyl group, A substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted A compound for an organic optoelectronic device, which is a dibenzothiophenyl group or a substituted or unsubstituted dibenzosilolyl group.
- 제1항에 있어서,According to claim 1,상기 Ar1 및 Ar2는 각각 독립적으로 하기 그룹 Ⅰ에 나열된 치환기 중에서 선택되는 어느 하나인, 유기 광전자 소자용 화합물:Wherein Ar 1 And Ar 2 Are each independently any one selected from the substituents listed in Group I, the compound for an organic optoelectronic device:[그룹 Ⅰ][Group I]
상기 그룹 Ⅰ에서, In group I,D는 중수소를 의미하고,D means deuterium,n15는 1 내지 5의 정수 중 하나이고,n15 is an integer from 1 to 5,n16은 1 내지 7의 정수 중 하나이고,n16 is one of integers from 1 to 7,n17은 1 내지 3의 정수 중 하나이고,n17 is one of integers from 1 to 3,n18은 1 내지 4의 정수 중 하나이고,n18 is one of integers from 1 to 4,*은 연결 지점이다.* is the connection point. - 제1항에 있어서,According to claim 1,상기 L1은 단일 결합이고,The L 1 is a single bond,상기 L2 및 L3은 각각 독립적으로 단일 결합, 또는 치환 또는 비치환된 페닐렌기인, 유기 광전자 소자용 화합물.The L 2 and L 3 are each independently a single bond, or a substituted or unsubstituted phenylene group, a compound for an organic optoelectronic device.
- 제1항에 있어서,According to claim 1,하기 그룹 1에 나열된 화합물 중에서 선택되는 하나인 유기 광전자 소자용 화합물:A compound for an organic optoelectronic device, which is one selected from the compounds listed in Group 1:[그룹 1] [Group 1][1-1] [1-2] [1-3] [1-4][1-1] [1-2] [1-3] [1-4]
[1-5] [1-6] [1-7] [1-8][1-5] [1-6] [1-7] [1-8]
[1-9] [1-10] [1-11] [1-12][1-9] [1-10] [1-11] [1-12]
[1-13] [1-14] [1-15] [1-16][1-13] [1-14] [1-15] [1-16]
[1-17] [1-18] [1-19] [1-20][1-17] [1-18] [1-19] [1-20]
[1-21] [1-22] [1-23] [1-24] [1-21] [1-22] [1-23] [1-24]
[1-25] [1-26] [1-27] [1-28] [1-25] [1-26] [1-27] [1-28]
[1-29] [1-30] [1-31] [1-32] [1-29] [1-30] [1-31] [1-32]
[1-33] [1-34] [1-35] [1-36] [1-33] [1-34] [1-35] [1-36]
[1-37] [1-38] [1-39] [1-40] [1-37] [1-38] [1-39] [1-40]
[1-41] [1-42] [1-43] [1-44] [1-41] [1-42] [1-43] [1-44]
[1-45] [1-46] [1-47] [1-48] [1-45] [1-46] [1-47] [1-48]
[1-49] [1-50] [1-51] [1-52] [1-49] [1-50] [1-51] [1-52]
[1-53] [1-54] [1-55] [1-56] [1-53] [1-54] [1-55] [1-56]
[1-57] [1-58] [1-59] [1-60] [1-57] [1-58] [1-59] [1-60]
[1-61] [1-62] [1-63] [1-64] [1-61] [1-62] [1-63] [1-64]
[1-65] [1-66] [1-67] [1-68] [1-65] [1-66] [1-67] [1-68]
[1-69] [1-70] [1-71] [1-72] [1-69] [1-70] [1-71] [1-72]
[1-73] [1-74] [1-75] [1-76] [1-73] [1-74] [1-75] [1-76]
[1-77] [1-78] [1-79] [1-80] [1-77] [1-78] [1-79] [1-80]
[1-81] [1-82] [1-83] [1-84] [1-81] [1-82] [1-83] [1-84]
[1-85] [1-86] [1-87] [1-88] [1-85] [1-86] [1-87] [1-88]
[1-89] [1-90] [1-91] [1-92][1-89] [1-90] [1-91] [1-92]
[1-93] [1-94] [1-95] [1-96][1-93] [1-94] [1-95] [1-96]
[1-97] [1-98] [1-99] [1-100][1-97] [1-98] [1-99] [1-100]
[1-101] [1-102] [1-103] [1-104][1-101] [1-102] [1-103] [1-104]
[1-105] [1-106] [1-107] [1-108][1-105] [1-106] [1-107] [1-108]
[1-109] [1-110] [1-111] [1-112][1-109] [1-110] [1-111] [1-112]
[1-113] [1-114] [1-115] [1-116][1-113] [1-114] [1-115] [1-116]
[1-117] [1-118] [1-119] [1-120][1-117] [1-118] [1-119] [1-120]
[1-121] [1-122] [1-123] [1-124][1-121] [1-122] [1-123] [1-124]
[1-125] [1-126] [1-127] [1-128][1-125] [1-126] [1-127] [1-128]
[1-129] [1-130] [1-131] [1-132][1-129] [1-130] [1-131] [1-132]
[1-133] [1-134] [1-135] [1-136][1-133] [1-134] [1-135] [1-136]
[1-137] [1-138] [1-139] [1-140][1-137] [1-138] [1-139] [1-140]
[1-141] [1-142] [1-143] [1-144][1-141] [1-142] [1-143] [1-144]
[1-145] [1-146] [1-147] [1-148][1-145] [1-146] [1-147] [1-148]
[1-149] [1-150] [1-151] [1-152][1-149] [1-150] [1-151] [1-152].
. - 제1 화합물 및 제2 화합물을 포함하고,a first compound and a second compound;상기 제1 화합물은 제1항에 따른 유기 광전자 소자용 화합물이며,The first compound is a compound for an organic optoelectronic device according to claim 1,상기 제2 화합물은 하기 화학식 3으로 표현되는 유기 광전자 소자용 화합물인, 유기 광전자 소자용 조성물:The second compound is a compound for an organic optoelectronic device represented by the following Chemical Formula 3, a composition for an organic optoelectronic device:[화학식 3][Formula 3]
상기 화학식 3에서,In Formula 3,X2는 O, S, N-La-Rb, CRcRd 또는 SiReRf이고,X 2 is O, S, NL a -R b , CR c R d or SiR e R f ,La는 단일결합, 또는 치환 또는 비치환된 C6 내지 C12 아릴렌기이고,L a is a single bond, or a substituted or unsubstituted C6 to C12 arylene group,Rb, Rc, Rd, Re, Rf 및 R6은 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C6 내지 C30 아릴기 또는 치환 또는 비치환된 C2 내지 C30 헤테로고리기이고,R b , R c , R d , R e , R f and R 6 are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,n6은 1 내지 4의 정수 중 하나이고,n6 is one of integers from 1 to 4,A는 하기 그룹 Ⅱ에 나열된 고리 중에서 선택되는 어느 하나이고,A is any one selected from the rings listed in Group II,[그룹 Ⅱ][Group II]
상기 그룹 Ⅱ에서,In group II,*은 연결 지점이고,* is the connection point,X3은 O 또는 S이고,X 3 is O or S,R7 내지 R14는 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C6 내지 C20 아릴기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로고리기이고,R 7 to R 14 are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,n7, n9, n12 및 n14는 각각 독립적으로 1 내지 4의 정수 중 하나이고,n7, n9, n12 and n14 are each independently an integer of 1 to 4,n8, n10, n11 및 n13은 각각 독립적으로 1 또는 2의 정수이고,n8, n10, n11 and n13 are each independently an integer of 1 or 2,Rb 및 R6 내지 R14 중 적어도 하나는 하기 화학식 a로 표현되는 기이고,At least one of R b and R 6 to R 14 is a group represented by the following formula (a),[화학식 a][Formula a]
상기 화학식 a에서,In the above formula (a),Z1 내지 Z3은 각각 독립적으로 N 또는 CRg이고,Z 1 to Z 3 are each independently N or CR g ,Z1 내지 Z3 중 적어도 둘은 N이고,At least two of Z 1 to Z 3 are N,Rg는 수소, 중수소, 치환 또는 비치환된 C1 내지 C30 알킬기, 또는 치환 또는 비치환된 C6 내지 C30 아릴기이고,R g is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,L4 내지 L6은 각각 독립적으로 단일 결합, 또는 치환 또는 비치환된 C6 내지 C30 아릴렌기이고,L 4 To L 6 are each independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group,Ar3 및 Ar4는 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로아릴기이고,Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,*는 연결 지점이다.* is the connection point. - 제10항에 있어서,11. The method of claim 10,상기 화학식 3은 하기 화학식 3-Ⅰ 내지 화학식 3-ⅩⅥ 중 어느 하나로 표현되는 유기 광전자 소자용 조성물:Chemical formula 3 is a composition for an organic optoelectronic device represented by any one of the following Chemical Formulas 3-I to 3-XVI:[화학식 3-Ⅰ] [Formula 3-Ⅰ]
상기 화학식 3-Ⅰ에서,In the formula 3-I,Z1 내지 Z3, R6, R7, L4 내지 L6, Ar3, Ar4, n6 및 n7은 전술한 바와 같고;Z 1 to Z 3 , R 6 , R 7 , L 4 to L 6 , Ar 3 , Ar 4 , n6 and n7 are as described above;[화학식 3-Ⅱ] [화학식 3-Ⅲ][Formula 3-Ⅱ] [Formula 3-Ⅲ]
[화학식 3-Ⅳ] [화학식 3-Ⅴ][Formula 3-IV] [Formula 3-V]
상기 화학식 3-Ⅱ 내지 화학식 3-Ⅴ에서,In the above formulas 3-II to 3-V,X2, Z1 내지 Z3, R6 내지 R9, L4 내지 L6, Ar3, Ar4, 및 n7 내지 n9는 제10항에서 정의한 바와 같고,X 2 , Z 1 to Z 3 , R 6 to R 9 , L 4 to L 6 , Ar 3 , Ar 4 , and n7 to n9 are as defined in claim 10,n6은 1 내지 3의 정수 중 하나이고;n6 is an integer from 1 to 3;[화학식 3-Ⅵ] [화학식 3-Ⅶ][Formula 3-VI] [Formula 3-VII]
[화학식 3-ⅤⅢ][Formula 3-VIII]
상기 화학식 3-Ⅵ 내지 화학식 3-ⅤⅢ에서,In Formulas 3-VI to 3-VIII,X2, Z1 내지 Z3, R6, R8, R9, L4 내지 L6, Ar3, Ar4, n6 및 n8은 제10항에서 정의한 바와 같고,X 2 , Z 1 to Z 3 , R 6 , R 8 , R 9 , L 4 to L 6 , Ar 3 , Ar 4 , n6 and n8 are as defined in claim 10,n9는 1 내지 3의 정수 중 하나이고;n9 is an integer from 1 to 3;[화학식 3-Ⅸ] [Formula 3-IX]
상기 화학식 3-Ⅸ에서, In the formula 3-IX,X2, Z1 내지 Z3, R6, R10 내지 R12, L4 내지 L6, Ar3, Ar4, n6, n10 및 n11은 제10항에서 정의한 바와 같고,X 2 , Z 1 to Z 3 , R 6 , R 10 to R 12 , L 4 to L 6 , Ar 3 , Ar 4 , n6, n10 and n11 are as defined in claim 10,n12는 1 내지 3의 정수 중 하나이며;n12 is an integer from 1 to 3;[화학식 3-Ⅹ][Formula 3-X]
상기 화학식 3-Ⅹ에서, In the formula 3-X,X2, X3, Z1 내지 Z3, R6, R13, R14, L4 내지 L6, Ar3, Ar4, n13 및 n14는 제10항에서 정의한 바와 같고,X 2 , X 3 , Z 1 to Z 3 , R 6 , R 13 , R 14 , L 4 to L 6 , Ar 3 , Ar 4 , n13 and n14 are as defined in claim 10,n6은 1 내지 3의 정수 중 하나이고;n6 is an integer from 1 to 3;[화학식 3-ⅩⅠ] [화학식 3-ⅩⅡ][Formula 3-XⅠ] [Formula 3-XII]
[화학식 3-ⅩⅢ][Formula 3-XIII]
[화학식 3-ⅩⅣ] [화학식 3-ⅩⅤ][Formula 3-XIV] [Formula 3-XV]
[화학식 3-ⅩⅥ][Formula 3-XVI]
상기 화학식 3-ⅩⅠ 내지 화학식 3-ⅩⅥ에서,In the above formulas 3-XI to 3-XVI,X2, X3, Z1 내지 Z3, R6, R8 내지 R13, L4 내지 L6, Ar3, Ar4, n6, n9, n10, n12 및 n14는 제10항에서 정의한 바와 같고,X 2 , X 3 , Z 1 to Z 3 , R 6 , R 8 to R 13 , L 4 to L 6 , Ar 3 , Ar 4 , n6, n9, n10, n12 and n14 are as defined in claim 10 and ,n8, n10 및 n13은 각각 독립적으로 1이다.n8, n10 and n13 are each independently 1; - 제10항에 있어서,11. The method of claim 10,상기 제2 화합물은 하기 화학식 3-Ⅱ, 화학식 3-Ⅲ 및 화학식 3-Ⅵ 중 어느 하나로 표현되는 유기 광전자 소자용 조성물.The second compound is a composition for an organic optoelectronic device represented by any one of Formula 3-II, Formula 3-III, and Formula 3-VI.
- 제10항에 있어서,11. The method of claim 10,상기 제2 화합물은 하기 화학식 3-Ⅱ-3, 화학식 3-Ⅲ-1, 화학식 3-Ⅵ-1 및 하기 화학식 3-Ⅵ-3 중 어느 하나로 표현되는 유기 광전자 소자용 조성물: The second compound is a composition for an organic optoelectronic device represented by any one of Formula 3-II-3, Formula 3-III-1, Formula 3-VI-1, and Formula 3-VI-3:[화학식 3-Ⅱ-3] [화학식 3-Ⅲ-1][Formula 3-Ⅱ-3] [Formula 3-III-1]
[화학식 3-Ⅵ-1] [화학식 3-Ⅵ-3][Formula 3-VI-1] [Formula 3-VI-3]
상기 화학식 3-Ⅰ-3, 화학식 3-Ⅲ-1, 화학식 3-Ⅵ-1 및 하기 화학식 3-Ⅵ-3에서,In Formula 3-I-3, Formula 3-III-1, Formula 3-VI-1, and Formula 3-VI-3,X2, Z1 내지 Z3, R6 내지 R9, L4 내지 L6, Ar3, Ar4 및 n6 내지 n8은 제10항에서 정의한 바와 같다.X 2 , Z 1 to Z 3 , R 6 to R 9 , L 4 to L 6 , Ar 3 , Ar 4 and n6 to n8 are as defined in claim 10 . - 제10항에 있어서,11. The method of claim 10,상기 Ar3 및 Ar4는 각각 독립적으로 치환 또는 비치환된 페닐기, 치환 또는 비치환된 바이페닐기, 치환 또는 비치환된 터페닐기, 치환 또는 비치환된 나프틸기, 치환 또는 비치환된 페난트레닐기, 치환 또는 비치환된 트리페닐렌기, 치환 또는 비치환된 카바졸일기, 치환 또는 비치환된 디벤조퓨란일기, 치환 또는 비치환된 디벤조티오펜일기, 또는 치환 또는 비치환된 디벤조실롤일기인, 유기 광전자 소자용 조성물.wherein Ar 3 and Ar 4 are each independently 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 phenanthrenyl group, A substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group , a composition for an organic optoelectronic device.
- 제10항에 있어서,11. The method of claim 10,상기 제2 화합물은 하기 그룹 2에 나열된 화합물 중에서 선택되는 하나인 유기 광전자 소자용 조성물:The second compound is a composition for an organic optoelectronic device which is one selected from the compounds listed in Group 2:[그룹 2][Group 2]
.
. - 서로 마주하는 양극과 음극,positive and negative poles facing each other,상기 양극과 상기 음극 사이에 위치하는 적어도 1층의 유기층을 포함하고,At least one organic layer positioned between the anode and the cathode,상기 유기층은 제1항 내지 제9항 중 어느 한 항에 따른 유기 광전자 소자용 화합물; 또는The organic layer is a compound for an organic optoelectronic device according to any one of claims 1 to 9; or제10항 내지 제15항 중 어느 한 항에 따른 유기 광전자 소자용 조성물을 포함하는 유기 광전자 소자.An organic optoelectronic device comprising the composition for an organic optoelectronic device according to any one of claims 10 to 15.
- 제16항에 있어서,17. The method of claim 16,상기 유기층은 발광층을 포함하고,The organic layer includes a light emitting layer,상기 발광층은 상기 유기 광전자 소자용 화합물 또는 상기 유기 광전자 소자용 조성물을 포함하는 유기 광전자 소자.The light emitting layer is an organic optoelectronic device comprising the compound for an organic optoelectronic device or the composition for an organic optoelectronic device.
- 제16항에 따른 유기 광전자 소자를 포함하는 표시 장치.A display device comprising the organic optoelectronic device according to claim 16 .
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