CN115669265A - 有机发光元件 - Google Patents
有机发光元件 Download PDFInfo
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- CN115669265A CN115669265A CN202180038014.0A CN202180038014A CN115669265A CN 115669265 A CN115669265 A CN 115669265A CN 202180038014 A CN202180038014 A CN 202180038014A CN 115669265 A CN115669265 A CN 115669265A
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- organic compound
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- 150000002894 organic compounds Chemical class 0.000 claims abstract description 243
- 239000000463 material Substances 0.000 claims abstract description 98
- 230000003111 delayed effect Effects 0.000 claims abstract description 55
- 150000001875 compounds Chemical class 0.000 claims description 103
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- 125000004429 atom Chemical group 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- 238000004020 luminiscence type Methods 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical group N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 218
- 125000001424 substituent group Chemical group 0.000 description 65
- 239000000126 substance Substances 0.000 description 61
- 239000010408 film Substances 0.000 description 60
- 239000000758 substrate Substances 0.000 description 43
- 230000000903 blocking effect Effects 0.000 description 41
- -1 diphenylamino group Chemical group 0.000 description 32
- 230000004888 barrier function Effects 0.000 description 27
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 26
- 238000002347 injection Methods 0.000 description 24
- 239000007924 injection Substances 0.000 description 24
- 230000005525 hole transport Effects 0.000 description 22
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- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- 238000000034 method Methods 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 13
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- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 10
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
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- 229910000831 Steel Inorganic materials 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 229910052805 deuterium Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- 230000005284 excitation Effects 0.000 description 3
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- 125000005647 linker group Chemical group 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
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- 125000004306 triazinyl group Chemical group 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 2
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 150000007978 oxazole derivatives Chemical class 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
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- 230000008569 process Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
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- 239000012780 transparent material Substances 0.000 description 2
- 125000005580 triphenylene group Chemical group 0.000 description 2
- 238000003631 wet chemical etching Methods 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 1
- GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-cycloheptadiene Chemical group C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- OYNJAUIAADXAOW-UHFFFAOYSA-N 2,3,5,6-tetra(carbazol-9-yl)benzene-1,4-dicarbonitrile Chemical compound C1=CC=CC=2C3=CC=CC=C3N(C1=2)C1=C(C(=C(C(=C1C#N)N1C2=CC=CC=C2C=2C=CC=CC1=2)N1C2=CC=CC=C2C=2C=CC=CC1=2)C#N)N1C2=CC=CC=C2C=2C=CC=CC1=2 OYNJAUIAADXAOW-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- XTVRLCUJHGUXCP-UHFFFAOYSA-N 3-methyleneheptane Chemical compound CCCCC(=C)CC XTVRLCUJHGUXCP-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical class C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
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- 229910004205 SiNX Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- OWXLRKWPEIAGAT-UHFFFAOYSA-N [Mg].[Cu] Chemical compound [Mg].[Cu] OWXLRKWPEIAGAT-UHFFFAOYSA-N 0.000 description 1
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- 125000005577 anthracene group Chemical group 0.000 description 1
- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical compound C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-UHFFFAOYSA-N 0.000 description 1
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- CHVJITGCYZJHLR-UHFFFAOYSA-N cyclohepta-1,3,5-triene Chemical group C1C=CC=CC=C1 CHVJITGCYZJHLR-UHFFFAOYSA-N 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical group C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
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- MNBNDZDPVOXAKJ-UHFFFAOYSA-N ethane;9h-fluorene Chemical class CC.C1=CC=C2CC3=CC=CC=C3C2=C1 MNBNDZDPVOXAKJ-UHFFFAOYSA-N 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
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- 239000011147 inorganic material Substances 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
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- 239000011777 magnesium Substances 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
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- 238000002834 transmittance Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
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| CN116368956A (zh) * | 2020-09-18 | 2023-06-30 | 三星显示有限公司 | 有机电致发光器件 |
| JP7780190B2 (ja) * | 2022-03-04 | 2025-12-04 | 株式会社Kyulux | 有機発光素子、遅延蛍光材料の評価方法、遅延蛍光材料の設計方法、有機発光素子の設計方法、およびプログラム |
| JP7780191B2 (ja) * | 2022-03-04 | 2025-12-04 | 株式会社Kyulux | 有機発光素子、遅延蛍光材料の評価方法、遅延蛍光材料の設計方法、有機発光素子の設計方法、およびプログラム |
| JP7780189B2 (ja) * | 2022-03-04 | 2025-12-04 | 株式会社Kyulux | 有機発光素子、遅延蛍光材料の評価方法、遅延蛍光材料の設計方法、有機発光素子の設計方法、およびプログラム |
| CN115745869B (zh) * | 2022-10-28 | 2025-05-13 | 清华大学 | 一种有机化合物及采用该化合物的有机电致发光器 |
| WO2025205402A1 (ja) * | 2024-03-29 | 2025-10-02 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子及び電子機器 |
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| JP5366106B1 (ja) | 2012-04-09 | 2013-12-11 | 国立大学法人九州大学 | 有機発光素子ならびにそれに用いる発光材料および化合物 |
| CN105074951B (zh) * | 2013-03-29 | 2017-09-22 | 九州有机光材股份有限公司 | 有机电致发光元件 |
| KR102577829B1 (ko) | 2013-08-14 | 2023-09-12 | 가부시키가이샤 큐럭스 | 유기 일렉트로루미네선스 소자 |
| EP3266772B1 (de) * | 2016-07-06 | 2019-04-24 | Cynora Gmbh | Organische moleküle, insbesondere zur verwendung in optoelektronischen vorrichtungen |
| DE102016113277A1 (de) * | 2016-07-19 | 2018-01-25 | Cynora Gmbh | Organische Moleküle zur Verwendung in optoelektronischen Bauelementen |
| KR102207689B1 (ko) * | 2016-08-24 | 2021-01-25 | 시노라 게엠베하 | 유기 분자, 특히 유기 광전자 디바이스에 사용하기 위한 유기 분자 |
| CN107778214B (zh) * | 2016-08-25 | 2020-03-31 | 西诺拉股份有限公司 | 有机分子，特别是用于有机光电器件的有机分子 |
| WO2018070348A1 (ja) * | 2016-10-13 | 2018-04-19 | シャープ株式会社 | 表示装置およびその製造方法 |
| KR102490154B1 (ko) | 2016-12-21 | 2023-01-18 | 고쿠리쓰다이가쿠호진 규슈다이가쿠 | 발광 재료, 화합물 및 유기 발광 소자 |
| JP2018111751A (ja) | 2017-01-10 | 2018-07-19 | 国立大学法人九州大学 | 発光材料、化合物および有機発光素子 |
| JP7226806B2 (ja) * | 2017-06-23 | 2023-02-21 | 株式会社Kyulux | 有機発光ダイオードに用いられる組成物 |
| US11584739B2 (en) * | 2017-06-23 | 2023-02-21 | Kyulux, Inc. | Composition of matter for use in organic light-emitting diodes |
| DE102017114345B4 (de) | 2017-06-28 | 2019-01-17 | Cynora Gmbh | Organische Moleküle, insbesondere zur Verwendung in organischen optoelektronischen Vorrichtungen |
| US11069860B2 (en) | 2017-08-21 | 2021-07-20 | Kyulux, Inc. | Composition of matter for use in organic light-emitting diodes |
| JP6776309B2 (ja) | 2018-03-30 | 2020-10-28 | キヤノン株式会社 | 有機発光素子、表示装置、撮像装置および照明装置 |
| DE102018114290B3 (de) | 2018-06-14 | 2019-06-06 | Cynora Gmbh | Organische Moleküle, insbesondere zur Verwendung in optoelektronischen Vorrichtungen |
| CN110759851A (zh) * | 2018-07-25 | 2020-02-07 | 北京鼎材科技有限公司 | 一种有机电致发光材料及其应用 |
| JP7325731B2 (ja) * | 2018-08-23 | 2023-08-15 | 国立大学法人九州大学 | 有機エレクトロルミネッセンス素子 |
| EP3670508B1 (en) * | 2018-12-20 | 2025-10-01 | Samsung Display Co., Ltd. | Organic molecules for use in optoelectronic devices |
| TWI851806B (zh) | 2019-09-05 | 2024-08-11 | 日商九州有機光材股份有限公司 | 用於有機發光二極體之物質組成物 |
| KR20210050829A (ko) * | 2019-10-29 | 2021-05-10 | 솔브레인 주식회사 | 화합물 및 이를 포함하는 유기 발광 소자 |
| KR102793989B1 (ko) * | 2019-11-08 | 2025-04-15 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자 및 유기 전계 발광 소자용 방향족 화합물 |
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