JP5241183B2 - キノキサリン誘導体、発光素子、発光装置及び電子機器 - Google Patents
キノキサリン誘導体、発光素子、発光装置及び電子機器 Download PDFInfo
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- JP5241183B2 JP5241183B2 JP2007238831A JP2007238831A JP5241183B2 JP 5241183 B2 JP5241183 B2 JP 5241183B2 JP 2007238831 A JP2007238831 A JP 2007238831A JP 2007238831 A JP2007238831 A JP 2007238831A JP 5241183 B2 JP5241183 B2 JP 5241183B2
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- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 title claims description 10
- 239000000463 material Substances 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 11
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- 238000002347 injection Methods 0.000 description 45
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- 238000000295 emission spectrum Methods 0.000 description 15
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- 125000003118 aryl group Chemical group 0.000 description 13
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 8
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- FEOWHLLJXAECMU-UHFFFAOYSA-N 4,7-dibromo-2,1,3-benzothiadiazole Chemical compound BrC1=CC=C(Br)C2=NSN=C12 FEOWHLLJXAECMU-UHFFFAOYSA-N 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
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- 230000005284 excitation Effects 0.000 description 6
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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 6
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- VPYOROSRDYVFDU-UHFFFAOYSA-N 2,3,5,8-tetraphenylquinoxaline Chemical compound C1=CC=CC=C1C(C1=NC(=C(C=2C=CC=CC=2)N=C11)C=2C=CC=CC=2)=CC=C1C1=CC=CC=C1 VPYOROSRDYVFDU-UHFFFAOYSA-N 0.000 description 5
- YDYISBUENKJUMI-UHFFFAOYSA-N 2,3-diphenyl-5,8-bis(2-phenylphenyl)quinoxaline Chemical compound C1=CC=CC=C1C1=CC=CC=C1C(C1=NC(=C(C=2C=CC=CC=2)N=C11)C=2C=CC=CC=2)=CC=C1C1=CC=CC=C1C1=CC=CC=C1 YDYISBUENKJUMI-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 5
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 238000002310 reflectometry Methods 0.000 description 5
- 239000000565 sealant Substances 0.000 description 5
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- 238000001308 synthesis method Methods 0.000 description 5
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 4
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 4
- YUQQAABAQIVPPC-UHFFFAOYSA-N 4,7-bis(2-phenylphenyl)-2,1,3-benzothiadiazole Chemical compound C1=CC=CC=C1C1=CC=CC=C1C(C1=NSN=C11)=CC=C1C1=CC=CC=C1C1=CC=CC=C1 YUQQAABAQIVPPC-UHFFFAOYSA-N 0.000 description 4
- DGYFWWPKSJCTTE-UHFFFAOYSA-N 4,7-dinaphthalen-1-yl-2,1,3-benzothiadiazole Chemical compound C1=CC=C2C(C3=CC=C(C4=NSN=C43)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 DGYFWWPKSJCTTE-UHFFFAOYSA-N 0.000 description 4
- VTRHMOORCMZQNN-UHFFFAOYSA-N 5,8-dinaphthalen-1-yl-2,3-diphenylquinoxaline Chemical compound C1=CC=CC=C1C1=NC2=C(C=3C4=CC=CC=C4C=CC=3)C=CC(C=3C4=CC=CC=C4C=CC=3)=C2N=C1C1=CC=CC=C1 VTRHMOORCMZQNN-UHFFFAOYSA-N 0.000 description 4
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
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- 150000004820 halides Chemical class 0.000 description 4
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000004544 sputter deposition Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- SGEOBWZVSUBWHX-UHFFFAOYSA-N 3,6-bis(2-phenylphenyl)benzene-1,2-diamine Chemical compound NC1=C(N)C(C=2C(=CC=CC=2)C=2C=CC=CC=2)=CC=C1C1=CC=CC=C1C1=CC=CC=C1 SGEOBWZVSUBWHX-UHFFFAOYSA-N 0.000 description 3
- QTHSFXSFJQHHHL-UHFFFAOYSA-N 3,6-dinaphthalen-1-ylbenzene-1,2-diamine Chemical compound C1=CC=C2C(C=3C(N)=C(C(=CC=3)C=3C4=CC=CC=C4C=CC=3)N)=CC=CC2=C1 QTHSFXSFJQHHHL-UHFFFAOYSA-N 0.000 description 3
- BFTONFBWVCVMTD-UHFFFAOYSA-N 4,7-diphenyl-2,1,3-benzothiadiazole Chemical compound C1=CC=CC=C1C(C1=NSN=C11)=CC=C1C1=CC=CC=C1 BFTONFBWVCVMTD-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000001413 cellular effect Effects 0.000 description 3
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- 125000005843 halogen group Chemical group 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
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- 239000011734 sodium Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 3
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- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 2
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 2
- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 0 Cc1c(*)c(*)c(*)c(*2)c1*C(c1ccccc1)=C2c1ccccc1 Chemical compound Cc1c(*)c(*)c(*)c(*2)c1*C(c1ccccc1)=C2c1ccccc1 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 2
- 229910001618 alkaline earth metal fluoride Inorganic materials 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000011152 fibreglass Substances 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 239000007769 metal material Substances 0.000 description 2
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- YRZZLAGRKZIJJI-UHFFFAOYSA-N oxyvanadium phthalocyanine Chemical compound [V+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 YRZZLAGRKZIJJI-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920002620 polyvinyl fluoride Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 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 2
- 229910052709 silver Inorganic materials 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
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| US10570113B2 (en) * | 2010-04-09 | 2020-02-25 | Semiconductor Energy Laboratory Co., Ltd. | Aromatic amine derivative, light-emitting element, light-emitting device, electronic device, and lighting device |
| KR101636968B1 (ko) * | 2013-10-29 | 2016-07-08 | 주식회사 엠비케이 | 신규한 전자주입 또는 수송층 화합물 및 이를 포함하는 유기전기발광소자 |
| KR102431667B1 (ko) * | 2017-09-21 | 2022-08-12 | 삼성디스플레이 주식회사 | 헤테로환 화합물, 이를 포함하는 유기 전계 발광 소자 및 유기 전계 발광 표시 장치 |
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| JP3621977B2 (ja) * | 1993-08-12 | 2005-02-23 | 隆一 山本 | 有機ｅｌ素子 |
| GB0004541D0 (en) * | 2000-02-25 | 2000-04-19 | Cambridge Display Tech Ltd | Luminescent polymer |
| JP3982164B2 (ja) * | 2000-09-26 | 2007-09-26 | 三菱化学株式会社 | 有機電界発光素子及びその製造方法 |
| JP4612846B2 (ja) * | 2005-02-09 | 2011-01-12 | キヤノン株式会社 | ビスキノキサリン化合物および有機発光素子 |
| DE102005058557A1 (de) * | 2005-12-08 | 2007-06-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
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