WO2017022730A1 - 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、及び電子機器 - Google Patents
化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、及び電子機器 Download PDFInfo
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- WO2017022730A1 WO2017022730A1 PCT/JP2016/072565 JP2016072565W WO2017022730A1 WO 2017022730 A1 WO2017022730 A1 WO 2017022730A1 JP 2016072565 W JP2016072565 W JP 2016072565W WO 2017022730 A1 WO2017022730 A1 WO 2017022730A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 158
- 239000000463 material Substances 0.000 title claims description 91
- 238000005401 electroluminescence Methods 0.000 title claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 233
- -1 biphenylyl group Chemical group 0.000 claims description 125
- 230000005525 hole transport Effects 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 53
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 239000010409 thin film Substances 0.000 claims description 28
- 230000000903 blocking effect Effects 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000001188 haloalkyl group Chemical group 0.000 claims description 19
- 125000004104 aryloxy group Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000006413 ring segment Chemical group 0.000 claims description 14
- 125000004434 sulfur atom Chemical group 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000000732 arylene group Chemical group 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000003808 silyl group Chemical class [H][Si]([H])([H])[*] 0.000 claims description 7
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 6
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 6
- 125000002908 as-indacenyl group Chemical group C1(=CC=C2C=CC3=CC=CC3=C12)* 0.000 claims description 6
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 6
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 6
- 125000001725 pyrenyl group Chemical group 0.000 claims description 6
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 claims description 5
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 5
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 4
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 4
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 claims description 4
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000005390 cinnolyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
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- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
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- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
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- 230000015572 biosynthetic process Effects 0.000 description 21
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- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- 229910052799 carbon Inorganic materials 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 239000002019 doping agent Substances 0.000 description 11
- 239000000956 alloy Substances 0.000 description 10
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- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 150000001342 alkaline earth metals Chemical class 0.000 description 7
- 239000011575 calcium Substances 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 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 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 6
- 239000012300 argon atmosphere Substances 0.000 description 6
- GQVWHWAWLPCBHB-UHFFFAOYSA-L beryllium;benzo[h]quinolin-10-olate Chemical compound [Be+2].C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21.C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21 GQVWHWAWLPCBHB-UHFFFAOYSA-L 0.000 description 6
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 6
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- 238000000576 coating method Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- 238000010992 reflux Methods 0.000 description 6
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- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 5
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 5
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- 150000004696 coordination complex Chemical class 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 229910052761 rare earth metal Inorganic materials 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 5
- 238000004544 sputter deposition Methods 0.000 description 5
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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 4
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
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- 238000004458 analytical method Methods 0.000 description 4
- 229910052792 caesium Inorganic materials 0.000 description 4
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000000434 field desorption mass spectrometry Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 description 4
- 229910003437 indium oxide Inorganic materials 0.000 description 4
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 4
- 229910001947 lithium oxide Inorganic materials 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
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- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 150000002910 rare earth metals Chemical class 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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- 238000001771 vacuum deposition Methods 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910052693 Europium Inorganic materials 0.000 description 3
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- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 3
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- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 3
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 3
- 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 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
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- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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Definitions
- the present invention relates to a compound, a material for an organic electroluminescence element, an organic electroluminescence element, and an electronic device.
- an organic electroluminescence element is composed of an anode, a cathode, and an organic thin film layer including one or more layers sandwiched between the anode and the cathode.
- organic EL element organic electroluminescence element
- a voltage is applied between both electrodes, electrons from the cathode side and holes from the anode side are injected into the light emitting region, and the injected electrons and holes recombine in the light emitting region to generate an excited state, which is excited.
- Light is emitted when the state returns to the ground state. Therefore, the development of a compound that efficiently transports electrons or holes to the light emitting region and facilitates recombination of electrons and holes is important in obtaining a high-efficiency organic EL device.
- Patent Document 1 describes a tertiary amine compound, for example, Compound H14, in which at least one dibenzofuran ring or dibenzothiophene ring is bonded to a central nitrogen atom via a linker. It is described that the compound described in Patent Document 1 can be used for a hole injection layer, a hole transport layer, a light emitting layer, and other layers of an organic EL element.
- Patent Document 2 describes tertiary amine compounds in which a 3-phenanthryl group is bonded to a central nitrogen atom directly or via a linker, for example, compounds 1-1, 4-2 and 4-3.
- these compounds can be used in a hole injection layer, a hole transport layer, a light emitting layer, and other layers of an organic EL device.
- these compounds are used in an electron blocking layer (EBL). ing.
- EBL electron blocking layer
- the present invention has been made to solve the above-described problems, and an object thereof is to provide an organic EL element that can be driven at a low voltage and a novel material that can realize such an organic EL element.
- an organic EL device capable of being driven at a low voltage can be obtained by using a compound represented by the following formula (1). It was. Furthermore, it discovered that a long-life organic EL element was obtained.
- R 1 to R 3 each independently represents an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, It represents one selected from the group consisting of a haloalkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, a halogen atom, and a cyano group.
- R 4 and R 5 are each independently an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, It represents one selected from the group consisting of a haloalkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, a halogen atom, and a cyano group.
- a is an integer from 0 to 4
- b is an integer from 0 to 2
- c is an integer from 0 to 3
- d is an integer from 0 to 3
- e is an integer from 0 to 4.
- (R 1 ) 0 , (R 2 ) 0 , (R 3 ) 0 , (R 4 ) 0 and (R 5 ) 0 are each absent R 1 , R 2 , R 3 , R 4 or R 5.
- the four R 5 s may be the same or different, and two adjacent groups selected from R 1 to R 5 are not bonded to each other to form a ring structure.
- L 1 to L 3 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.
- Ar is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 12 ring atoms, or a hetero atom contained in the ring as an oxygen atom and a sulfur atom.
- substituted or unsubstituted include alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 18 ring carbon atoms, cycloalkyl groups having 3 to 50 ring carbon atoms, and ring formation.
- [2] A material for an organic electroluminescence device comprising the compound (1) according to the above [1].
- An electronic device comprising the organic electroluminescence element according to [3].
- the organic EL device produced using the compound (1) can be driven at a low voltage.
- the “carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY” represents the number of carbon atoms when the ZZ group is unsubstituted. The carbon number of the substituent in the case where it is present is not included.
- the “atom number XX to YY” in the expression “a ZZ group having a substituted or unsubstituted atom number XX to YY” represents the number of atoms when the ZZ group is unsubstituted. In this case, the number of substituent atoms is not included.
- unsubstituted ZZ group in the case of “substituted or unsubstituted ZZ group” means that the hydrogen atom of the ZZ group is not substituted with a substituent.
- hydroxogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (protium), deuterium (deuterium), and tritium (tritium).
- the “ring-forming carbon number” means the ring itself of a compound having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound). This represents the number of carbon atoms among the constituent atoms.
- the carbon contained in the substituent is not included in the ring-forming carbon.
- the “ring-forming carbon number” described below is the same unless otherwise specified.
- a benzene ring has 6 ring carbon atoms
- a naphthalene ring has 10 ring carbon atoms
- a pyridine ring has 5 ring carbon atoms
- a furan ring has 4 ring carbon atoms.
- the carbon number of the alkyl group is not included in the number of ring-forming carbons.
- the number of carbon atoms of the fluorene ring as a substituent is not included in the number of carbon atoms forming the ring.
- the “number of ring-forming atoms” means a compound (for example, a monocyclic compound, a condensed ring compound, a bridging compound, or a carbon) having a structure in which atoms are bonded in a cyclic manner (for example, a single ring, a condensed ring, or a ring assembly).
- Ring compound, heterocyclic compound represents the number of atoms constituting the ring itself.
- An atom that does not constitute a ring for example, a hydrogen atom that terminates a bond of an atom that constitutes a ring
- an atom contained in a substituent when the ring is substituted by a substituent is not included in the number of ring-forming atoms.
- the “number of ring-forming atoms” described below is the same unless otherwise specified.
- the pyridine ring has 6 ring atoms
- the quinazoline ring has 10 ring atoms
- the furan ring has 5 ring atoms.
- the hydrogen atoms bonded to the ring-forming carbon atoms of the pyridine ring and quinazoline ring and the atoms constituting the substituent are not included in the number of ring-forming atoms.
- a fluorene ring is bonded to the fluorene ring as a substituent (including a spirobifluorene ring)
- the number of atoms of the fluorene ring as a substituent is not included in the number of ring-forming atoms.
- the examples described for one group, preferred examples thereof, and the like can be arbitrarily combined with any of those described for other groups. Further, a group arbitrarily selected from the examples described for one group, preferred examples thereof, and the like can be combined with a group arbitrarily selected from the examples described for other groups, preferred examples thereof, and the like. Similarly, the number of atoms, the number of carbon atoms, and other aspects can be arbitrarily combined. The same applies to the combinations of the above groups, the number of atoms, the number of carbon atoms, and other aspects.
- the compound according to one embodiment of the present invention is represented by the formula (1).
- R 1 to R 3 each independently represents an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, It represents one selected from the group consisting of a haloalkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, a halogen atom, and a cyano group.
- R 4 and R 5 are each independently an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, It represents one selected from the group consisting of a haloalkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, a halogen atom, and a cyano group.
- a is an integer from 0 to 4
- b is an integer from 0 to 2
- c is an integer from 0 to 3
- d is an integer from 0 to 3
- e is an integer from 0 to 4.
- (R 1 ) 0 , (R 2 ) 0 , (R 3 ) 0 , (R 4 ) 0 and (R 5 ) 0 are each absent R 1 , R 2 , R 3 , R 4 or R 5.
- the four R 5 s may be the same or different, and two adjacent groups selected from R 1 to R 5 are not bonded to each other to form a ring structure.
- L 1 to L 3 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.
- Ar is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 12 ring atoms, or a hetero atom contained in the ring as an oxygen atom and a sulfur atom. And represents a substituted or unsubstituted heteroaryl group having 13 to 50 ring atoms, which is at least one selected from the group consisting of X is an oxygen atom or a sulfur atom.
- the optional substituents when referred to as “substituted or unsubstituted” are: an alkyl group having 1 to 20 carbon atoms; an aryl group having 6 to 18 ring carbon atoms; a cycloalkyl group having 3 to 50 ring carbon atoms; An aralkyl group having 7 to 30 carbon atoms having an aryl group having 6 to 18 carbon atoms; an alkoxy group having 1 to 20 carbon atoms; an aryloxy group having 6 to 18 ring carbon atoms; an alkyl group having 1 to 20 carbon atoms and a ring Mono-substituted, di-substituted or tri-substituted silyl groups having a substituent selected from aryl groups having 6 to 18 carbon atoms; haloalkyl groups having 1 to 20 carbon atoms; haloalkoxy groups having 1 to 20 carbon atoms; halogen atoms; A group selected from the group consisting of a group and
- the compound (1) is preferably a compound represented by any of the following formulas (2) to (5).
- R 1 to R 5 , a to e, L 1 to L 3 , Ar and X are as defined in the formula (1).
- R 1 to R 3 each independently represents an alkyl group having 1 to 20 carbon atoms, preferably 1 to 5 carbon atoms, more preferably 1 to 4 carbon atoms; 3 to 50 ring carbon atoms, preferably 3 to 10 carbon atoms.
- R 1 to R 3 are each independently preferably composed of an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, an aryloxy group having 6 to 50 ring carbon atoms, and a cyano group. It is one selected from the group, more preferably an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 18 ring carbon atoms.
- R 4 and R 5 are each independently an alkyl group having 1 to 20 carbon atoms, preferably 1 to 5 carbon atoms, more preferably 1 to 4 carbon atoms; 3 to 50 ring carbon atoms, preferably 3 to 10 carbon atoms. More preferably a cycloalkyl group having 3 to 6 carbon atoms; a haloalkyl group having 1 to 20 carbon atoms, preferably 1 to 5 carbon atoms, more preferably 1 to 4 carbon atoms; 1 to 20 carbon atoms, preferably 1 to 5 carbon atoms; More preferably an alkoxy group having 1 to 4 carbon atoms; a haloalkoxy group having 1 to 20 carbon atoms, preferably 1 to 5 carbon atoms, more preferably 1 to 4 carbon atoms; an aryl group having 6 to 18 ring carbon atoms, preferably 6 to 12 carbon atoms; An aryloxy group having 6 to 18, preferably 6 to 12 ring carbon atoms; a halogen atom; or
- alkyl group having 1 to 20 carbon atoms examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group (isomer) ), Hexyl group (including isomer), heptyl group (including isomer), octyl group (including isomer), nonyl group (including isomer), decyl group (including isomer), undecyl Groups (including isomers) and dodecyl groups (including isomers), such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t- A butyl group or a pentyl group (including isomers) is preferable, and a methyl group, ethyl group, n-propy
- Examples of the cycloalkyl group having 3 to 50 ring carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
- haloalkyl group having 1 to 20 carbon atoms examples include, for example, at least one, preferably 1 to 7 hydrogen atoms, or all hydrogen atoms of the above-described alkyl group having 1 to 20 carbon atoms, fluorine atom, chlorine atom , A bromine atom, and a halogen atom selected from the group consisting of iodine atoms, preferably a group obtained by substitution with a fluorine atom.
- haloalkyl group a heptafluoropropyl group (including isomers), a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, or a trifluoromethyl group is preferable, and a pentafluoroethyl group, 2,2, A 2-trifluoroethyl group or a trifluoromethyl group is more preferable, and a trifluoromethyl group is still more preferable.
- the alkoxy group having 1 to 20 carbon atoms is represented by —OR 11 , and R 11 represents the above alkyl group having 1 to 20 carbon atoms.
- the alkoxy group is preferably a t-butoxy group, a propoxy group (including isomers), an ethoxy group, or a methoxy group, more preferably an ethoxy group or a methoxy group, and even more preferably a methoxy group.
- the haloalkoxy group having 1 to 20 carbon atoms is represented by —OR 12 , and R 12 represents the above haloalkyl group having 1 to 20 carbon atoms, preferably a fluoroalkyl group having 1 to 20 carbon atoms.
- the haloalkoxy group is preferably a heptafluoropropoxy group (including isomers), a pentafluoroethoxy group, a 2,2,2-trifluoroethoxy group, or a trifluoromethoxy group, preferably a pentafluoroethoxy group, 2,2 1,2-trifluoroethoxy group or trifluoromethoxy group is more preferable, and trifluoromethoxy group is more preferable.
- aryl group having 6 to 18 ring carbon atoms examples include a phenyl group, biphenylyl group, terphenylyl group, biphenylenyl group, naphthyl group, acenaphthylenyl group, anthryl group, benzoanthryl group, aceanthryl group, phenanthryl group (“ Phenanthrenyl group ”), benzophenanthryl group, triphenylenyl group, phenenylenyl group, fluorenyl group, benzofluorenyl group, pyrenyl group, chrysenyl group, s-indacenyl group, as-indacenyl group, and fluoranthenyl group
- a phenyl group, a biphenylyl group, a terphenylyl group, or a naphthyl group is preferable, a phenyl group, a biphenylyl group, or a nap
- Examples of the naphthyl group include 1- or 2-naphthyl group
- examples of the biphenylyl group include 2-, 3- or 4-biphenylyl group
- examples of the terphenyl group include 2 -P-terphenylyl group, 4-p-terphenylyl group, 2'-m-terphenylyl group, and 5'-m-terphenylyl group can be mentioned.
- R 5 is a biphenylyl group, it is preferably a 3-biphenylyl group.
- the aryloxy group having 6 to 18 ring carbon atoms is represented by —OR 13 , and R 13 represents an aryl group having 6 to 18 ring carbon atoms, preferably 6 to 12 carbon atoms.
- R 13 represents an aryl group having 6 to 18 ring carbon atoms, preferably 6 to 12 carbon atoms.
- the aryl group include a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, an acenaphthylenyl group, an anthryl group, a benzoanthryl group, an aceanthryl group, a phenanthryl group, a benzophenanthryl group, a triphenylenyl group, A phenalenyl group, a fluorenyl group, a benzofluorenyl group, a pyrenyl group, a chryceny
- the halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a fluorine atom.
- a is an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 0 or 1.
- b is an integer of 0 to 2, preferably 0 or 1.
- c is an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 0 or 1.
- d is an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 0 or 1.
- e is an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 0 or 1.
- each of a to e is 0, that is, (R 1 ) 0 , (R 2 ) 0 , (R 3 ) 0 , (R 4 ) 0 , or (R 5 ) 0 is respectively R 1 , R 2 , R 3 , R 4 , or R 5 is absent, that is, not substituted with R 1 , R 2 , R 3 , R 4 , or R 5 .
- a, b, c, d or e represents an integer of 2 or more, 2 to 4 R 1 , 2 R 2 , 2 or 3 R 3 , 2 or 3 R 4 , and 2 Up to 4 R 5 s may be the same or different. Two adjacent groups selected from R 1 to R 5 are not bonded to each other to form a ring structure.
- Ar represents a substituted or unsubstituted aryl group having 6 to 50, preferably 6 to 24, more preferably 6 to 12 ring carbon atoms; a substituted or unsubstituted heteroaryl group having 5 to 12 ring atoms; or
- the number of substituted or unsubstituted ring-forming atoms in which at least one hetero atom contained in the ring is at least one selected from oxygen and sulfur atoms is 13 to 50, preferably 13 to 30, more preferably 13 to 24, and still more preferably Represents 13-18 heteroaryl groups.
- the heteroaryl group include heteroaryl groups having preferably 1 to 5, more preferably 1 to 3, and still more preferably 1 to 2 ring-forming heteroatoms.
- examples of the aryl group having 6 to 50 ring carbon atoms include a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, an acenaphthylenyl group, an anthryl group, a benzoanthryl group, an aceanthryl group, 2- Phenanthryl group, benzophenanthryl group, phenalenyl group, fluorenyl group, benzofluorenyl group, 9,9'-spirobifluorenyl group, pentacenyl group, picenyl group, pentaphenyl group, pyrenyl group, chrysenyl group, benzocrisenyl group Group, s-indacenyl group, as-indacenyl group, fluoranthenyl group, and perylenyl group.
- aryl group for example, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, or a fluorenyl group is preferable.
- substituted aryl group for example, a 9,9-diphenylfluorenyl group is preferable.
- the heteroaryl group having 5 to 12 ring atoms includes, for example, a pyrrolyl group, a furyl group (also referred to as “furanyl group”, the same shall apply hereinafter), a thienyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group.
- the heteroaryl group having 13 to 50 ring atoms in which the hetero atom is an oxygen atom or a sulfur atom is, for example, a dibenzofuranyl group, a naphthobenzofuranyl group, a dibenzothiophenyl group (“dibenzothienyl group”).
- dibenzofuranyl group a naphthobenzofuranyl group
- dibenzothiophenyl group a dibenzothiophenyl group
- a naphthobenzothiophenyl group also referred to as “naphthobenzothienyl group”, the same applies hereinafter
- a phenoxazinyl group and a xanthenyl group.
- the substituted heteroaryl group for example, a dibenzofuranyl group or a dibenzothiophenyl group is preferable.
- L 1 to L 3 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 30, preferably 6 to 24, more preferably 6 to 12 ring-forming carbon atoms.
- an arylene group having 6 to 30 ring carbon atoms is a group obtained by removing one hydrogen atom from an aryl group having 6 to 30 ring carbon atoms.
- the aryl group include a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, an acenaphthylenyl group, an anthryl group, a benzoanthryl group, an aceanthryl group, a 2-phenanthryl group, a benzophenanthryl group, a triphenylenyl group.
- phenalenyl group for example, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, or a fluorenyl group is preferable.
- substituted arylene group for example, a group obtained by removing one hydrogen atom from a 9,9-diphenylfluorenyl group is preferable.
- an optional substituent when “substituted or unsubstituted” is an alkyl group having 1 to 20, preferably 1 to 5, more preferably 1 to 4 carbon atoms; ring-forming carbon An aryl group having 6 to 18, preferably 6 to 12, more preferably 6 to 10, more preferably 6; a ring-forming carbon number of 3 to 50, preferably 3 to 10, more preferably 3 to 6, More preferably, a cycloalkyl group having 5 or 6; an aralkyl group having 7 to 30 carbon atoms having an aryl group having 6 to 18, preferably 6 to 12, more preferably 6 to 10, and still more preferably 6 ring-forming carbon atoms; An alkoxy group having 1 to 20 carbon atoms, preferably 1 to 5 carbon atoms, more preferably 1 to 4 carbon atoms; an aryloxy group having 6 to 18 ring carbon atoms, preferably 6 to 12 carbon atoms, and more preferably 6 carbon atoms; ,Preferably Mono
- a plurality of the arbitrary substituents may be the same or different.
- the aryl group having 6 to 18 ring carbon atoms is as described above.
- Specific examples thereof include, for example, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, propyldimethylsilyl group, isopropyldimethylsilyl group, triphenylsilyl group, phenyldimethylsilyl group, t-butyldiphenylsilyl group, and tri A tolylsilyl group is mentioned.
- Ar is independently represented by one selected from the group consisting of the following formulas (a) to (m).
- * represents a bond with L 1 in the formulas (1) to (5).
- each R is independently selected from the substituents described above with respect to any substituents when referred to as “substituted or unsubstituted” in the formulas (1) to (5),
- the preferable range is also the same.
- each p independently represents an integer of 0 to 5, preferably an integer of 0 to 3, more preferably 0 or 1, and still more preferably 0.
- Each q independently represents an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 0 or 1, and still more preferably 0.
- Each r independently represents an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 0 or 1, and still more preferably 0.
- s represents an integer of 0 to 2, preferably 0 or 1, more preferably 0.
- t represents 0 or 1, preferably 0.
- each (R) 0 means that R is not present, ie, not substituted with R.
- the groups represented by formulas (a) to (m) preferably have 1 or 2 Rs, and more preferably have 1 R.
- R a and R b are each independently an alkyl group having 1 to 20 carbon atoms, preferably 1 to 5 carbon atoms, more preferably 1 to 4 carbon atoms; 6 to 18 ring carbon atoms, preferably 6 carbon atoms.
- R a and R b are each independently selected from aryl groups having 6 to 12 ring carbon atoms, and more preferably selected from phenyl groups.
- Y represents a nitrogen atom, an oxygen atom, or a sulfur atom.
- Y is preferably an oxygen atom or a sulfur atom, more preferably a sulfur atom.
- two adjacent Rs may be bonded to each other, and a ring structure may be formed together with the ring-forming carbon atom to which the two adjacent Rs are bonded.
- two selected from R, R a and R b may be bonded to each other to form a ring structure.
- the ring structure an aromatic hydrocarbon ring such as a benzene ring or an aromatic heterocycle having a ring-forming heteroatom such as an oxygen atom or a sulfur atom is preferable.
- two adjacent Rs may not be bonded to each other.
- Two members selected from R, R a and R b may be bonded to each other to form a ring structure.
- two adjacent Rs are not bonded to each other to form a ring structure.
- the groups represented by the formulas (a) to (o) preferably have 1 or 2 Rs. More preferably.
- the hydrogen atoms on the groups represented by formulas (a) to (o) are not substituted with R, ie, p to t It is preferred that all of are zero.
- Formula (b) preferably represents a 2-biphenylyl group, a 3-biphenylyl group or a 4-biphenylyl group each optionally substituted by R.
- Formula (c) is preferably a 2-, 3- or 4-p-terphenylyl group, a 2-, 3- or 4-m-terphenylyl group, or 2-, 3 each optionally substituted by R.
- Formula (d) is preferably a 2′-p-terphenylyl group, 2′-, 4′-, or 5′-m-terphenylyl group, or 4′-o-, each optionally substituted with R. Represents a terphenylyl group.
- Formula (e) preferably represents a 1-naphthyl group or a 2-naphthyl group, each of which may be substituted with R.
- Formula (f) represents a 2-phenanthryl group which may be substituted with R.
- R a and R b both represent a phenyl group, or one of R a and R b represents a methyl group and the other represents a phenyl group. More preferably, R a and R b are both phenyl groups.
- the group represented by the formula (g) is bonded to L 1 of the formulas (1) to (5) at the 1 to 4 position, preferably the 2 or 4 position, more preferably the 2 position of the fluorene ring.
- Formula (h) preferably represents a 4- (9-phenylfluoren-9-yl) phenyl group which may be substituted with R.
- the group represented by the formula (i) is bonded to L 1 of the formulas (1) to (5) at the 1 to 4 position, preferably the 2 or 4 position of the fluorene ring.
- the group represented by the formula (j) is preferably bonded to L 1 of the formulas (1) to (5) at the 2-position of the thiophene ring.
- the group represented by the formula (k) is preferably bonded to L 1 of the formulas (1) to (5) at the 2-position of the benzothiophene ring.
- the group represented by the formula (l) is bonded to L 1 of the formulas (1) to (5) at the 1 to 4 position, preferably the 2 or 4 position of the dibenzofuran ring.
- the group represented by the formula (m) is bonded to L 1 of the formulas (1) to (5) at the 1 to 4 position, preferably the 2 or 4 position of the dibenzothiophene ring.
- Ar independently represents each of the following formulas (b-1), (b-2), (b-3), (c-1 ), (C-2), (c-3), (d-1), (d-2), (d-3), (e-1), (f), (g-1), (i -1), (i-2), (l-1), (l-2), (m-1), or (m-2).
- each of L 1 to L 3 may be a single bond, or each of L 1 to L 3 may form a substituted or unsubstituted ring. It may be an arylene group having 6 to 30 carbon atoms, preferably 6 to 24 carbon atoms, more preferably 6 to 12 carbon atoms. In one embodiment of the compounds represented by formulas (1) to (5), L 3 is preferably a single bond. In one embodiment of the compounds represented by formulas (1) to (5), L 2 is preferably a substituted or unsubstituted ring-forming carbon number of 6 to 30, more preferably 6 to 24, still more preferably 6 to 12 arylene groups.
- the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms represented by L 1 to L 3 is preferably represented by the following formula (ii) or (iii).
- R and q are as defined for formulas (a) to (m).
- L 1 is represented by the formula (ii) or (iii)
- * and ** represents a bond with Ar in the formulas (1) to (5)
- the other represents the formula (1) to (5) Represents a bond with a nitrogen atom in it.
- Formulas (ii) and (iii) are preferably represented by the following formulas.
- Formula (ii) is more preferably a p-phenylene group.
- Ar is represented by the formula (b-1), (b-2), (b-3), (c-1), (c-2), Any one selected from the group consisting of (c-3), (d-1), (d-3), (f), (g-1), (i-1), and (i-2) A compound of formula (2) or formula (3), wherein L 1 and L 3 are single bonds, and L 2 is a group represented by formula (ii); Ar is a group represented by the formula (b-1), (b-2), (c-1), or (g-1), L 1 is a single bond, L 2 and L 3 Is a group represented by formula (ii), a compound of formula (2) or formula (3); Ar is a group represented by the formula (d-2), (e-1), (l-1), (l-2), (m-1), or (m-2), and L A compound of formula (2) or formula (3), wherein 1 and L 2 are a group represented by the formula (ii), and L 3 is a group represented by a single bond; Ar is a group represented by the formula (b-1), (b-2), (b
- a compound of formula (4) or formula (5), and Ar is a group represented by formula (b-1) or (c-1), and L 1 and L 3 are A bond, L 2 is a group represented by the formula (ii), R 4 is a phenyl group, R 5 is a phenyl group or a biphenyl group, d is 0 or 1, and e is 1 Is a compound selected from the group consisting of compounds of formula (2) or formula (3).
- the material for an organic EL device which is one embodiment of the present invention includes a compound represented by the above formula (1) (compound (1)) and a group consisting of the compounds represented by the above formulas (2) to (5). It is preferable to include at least one selected from the above.
- the description relating to the compound (1) includes the compound (1), the compounds represented by the formulas (2) to (5) included therein, and the respective compounds of the subordinate concept included therein. Can be read and replaced.
- Content of the compound (1) in the organic EL device material which is one embodiment of the present invention is not particularly limited, and may be, for example, 1% by mass or more (including 100% by mass), and 10% by mass or more ( 100% by mass), preferably 50% by mass or more (including 100% by mass), more preferably 80% by mass or more (including 100% by mass), and 90% by mass. % Or more (including 100% by mass) is even more preferable.
- the organic EL device material which is one embodiment of the present invention is useful as a material for manufacturing an organic EL device, for example, a host material and a dopant material in a light emitting layer of a fluorescent light emitting unit, or a host in a light emitting layer of a phosphorescent light emitting unit.
- an anode-side organic thin film layer such as a hole transport layer, a hole injection layer, and an electron blocking layer provided between the anode and the light emitting layer, and a cathode and the light emitting layer. It is also useful as a material for cathode-side organic thin film layers such as an electron transport layer, an electron injection layer, and a hole blocking layer provided therebetween.
- the anode-side organic thin film layer may be a multilayer including two or more layers, and the two or more layers may be a hole transport layer.
- the organic EL device material of the present invention may be contained in any one of the two or more hole transport layers. That is, the organic EL device material of the present invention may be used for any of the hole transport layer closest to the light emitting layer, the hole transport layer closest to the anode, and the hole transport layer located in the middle.
- An organic EL element which is one embodiment of the present invention will be described.
- An organic EL element has an organic thin film layer including one or more layers between a cathode and an anode.
- the organic thin film layer includes a light emitting layer, and at least one of the organic thin film layers includes the compound (1).
- Examples of the organic thin film layer containing the compound (1) include an anode-side organic thin film layer (hole transport layer, hole injection layer, electron blocking layer, exciton blocking layer) provided between the anode and the light emitting layer. Etc.), a light emitting layer, a space layer, a blocking layer and the like, but are not limited thereto.
- the compound (1) can be included in any hole transport layer. That is, the compound (1) may be contained in any of the hole transport layer closest to the light emitting layer, the hole transport layer closest to the anode, and the hole transport layer located in the middle.
- the organic EL element which is one embodiment of the present invention may be a fluorescent or phosphorescent monochromatic light emitting element, a fluorescent / phosphorescent hybrid white light emitting element, or a simple type having a single light emitting unit. Alternatively, a tandem type having a plurality of light emitting units may be used.
- the “light emitting unit” includes an organic thin film layer including one or more layers, at least one of which is a light emitting layer, and is a minimum unit that emits light by recombination of injected holes and electrons.
- typical element configurations of simple organic EL elements include the following element configurations.
- the light-emitting unit may be a laminated type having a plurality of phosphorescent light-emitting layers and fluorescent light-emitting layers.
- a space layer may be provided in order to prevent the excitons from diffusing into the fluorescent light emitting layer.
- a typical layer structure of the simple light emitting unit is shown below. The layers in parentheses are optional.
- Each phosphorescent or fluorescent light-emitting layer may have a different emission color.
- the layer structure include a light emitting layer (blue light emission) / electron transport layer.
- An electron barrier layer may be appropriately provided between each light emitting layer and the hole transport layer or space layer.
- a hole blocking layer may be appropriately provided between each light emitting layer and the electron transport layer.
- the following element structure can be mentioned as a typical element structure of a tandem type organic EL element.
- Anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode As the first light-emitting unit and the second light-emitting unit, for example, the above-mentioned simple light-emitting units are cited as examples independently of each other. Each light emitting unit can be selected.
- the intermediate layer is generally called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, or an intermediate insulating layer, and has electrons in the first light emitting unit and holes in the second light emitting unit.
- a known material structure to be supplied can be used.
- FIG. 1 shows a schematic configuration of an example of the organic EL element.
- the organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and a light emitting unit 10 disposed between the anode 3 and the cathode 4.
- the light emitting unit 10 has at least one light emitting layer 5.
- Hole injection / transport layer 6 anode-side organic thin film layer
- electron injection / transport layer 7 cathode-side organic thin film layer
- an electron barrier layer (not shown) may be provided on the anode 3 side of the light emitting layer 5, and a hole barrier layer (not shown) may be provided on the cathode 4 side of the light emitting layer 5.
- a host combined with a fluorescent dopant is called a fluorescent host
- a host combined with a phosphorescent dopant is called a phosphorescent host
- the fluorescent host and the phosphorescent host are not distinguished only by the molecular structure. That is, the phosphorescent host means a material for forming a phosphorescent light emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material for forming a fluorescent light emitting layer. The same applies to the fluorescent host.
- the substrate is used as a support for the organic EL element.
- a plate made of glass, quartz, plastic, or the like can be used.
- a flexible substrate may be used.
- the flexible substrate is a substrate that can be bent (flexible), and examples thereof include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. .
- an inorganic vapor deposition film can also be used.
- a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function specifically, 4.0 eV or more.
- ITO indium tin oxide
- indium oxide-tin oxide containing silicon or silicon oxide indium oxide-zinc oxide
- indium oxide containing tungsten oxide and zinc oxide examples include graphene.
- gold Au
- platinum Pt
- nickel Ni
- tungsten W
- Cr chromium
- Mo molybdenum
- iron Fe
- Co cobalt
- Cu copper
- palladium Pd
- titanium Ti
- a nitride of the metal for example, titanium nitride
- indium oxide-zinc oxide is a target in which 1 to 10% by mass of zinc oxide is added to indium oxide, and indium oxide containing tungsten oxide and zinc oxide is 0.5 to 0.5% in tungsten oxide relative to indium oxide.
- a target containing 5% by mass and zinc oxide of 0.1 to 1% by mass it can be formed by a sputtering method.
- the hole injection layer formed in contact with the anode is formed using a material that is easy to inject holes regardless of the work function of the anode, a material generally used as an electrode material (for example, a metal, an alloy, an electrically conductive compound, a mixture thereof, and an element belonging to Group 1 or Group 2 of the periodic table of elements may be used.
- a material generally used as an electrode material For example, a metal, an alloy, an electrically conductive compound, a mixture thereof, and an element belonging to Group 1 or Group 2 of the periodic table of elements may be used.
- An element belonging to Group 1 or Group 2 of the periodic table which is a material having a low work function, that is, an alkali metal such as lithium (Li) or cesium (Cs), and magnesium (Mg), calcium (Ca), Alkaline earth metals such as strontium (Sr) and alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these can also be used.
- an alkali metal such as lithium (Li) or cesium (Cs)
- Mg calcium
- Alkaline earth metals such as strontium (Sr) and alloys containing these
- MgAg, AlLi Alkaline earth metals
- rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these
- a vacuum evaporation method or a sputtering method can be used.
- the hole injection layer is a layer containing a material having a high hole injection property (hole injection material). You may use the said compound of this invention in a hole injection layer individually or in combination with the following material.
- Hole injection materials include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide Products, manganese oxides, and the like can be used.
- Polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used.
- poly (N-vinylcarbazole) (abbreviation: PVK)
- poly (4-vinyltriphenylamine) (abbreviation: PVTPA)
- PVTPA poly (4-vinyltriphenylamine)
- PTPDMA poly [N- (4- ⁇ N ′-[4- (4-diphenylamino)] Phenyl] phenyl-N′-phenylamino ⁇ phenyl) methacrylamide]
- PTPDMA poly [N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl) benzidine]
- Polymer compounds such as Poly-TPD).
- a polymer compound to which an acid such as poly (3,4-ethylenedioxythiophene) / poly (styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly (styrenesulfonic acid) (PAni / PSS) is added is used. You can also.
- a receptive compound such as a hexaazatriphenylene (HAT) compound represented by the following formula (K) may be used in combination with the compound of the present invention.
- HAT hexaazatriphenylene
- R 21 to R 26 may be the same as or different from each other, and each independently represents a cyano group, —CONH 2 , a carboxyl group, or —COOR 27 (R 27 is a group having 1 to 20 carbon atoms) Represents an alkyl group or a cycloalkyl group having 3 to 20 carbon atoms, and in R 21 and R 22 , R 23 and R 24 , and R 25 and R 26 , two adjacent groups are bonded to each other.
- R 27 examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.
- the hole transport layer is a layer containing a material having a high hole transport property (hole transport material). You may use the said compound (1) for a positive hole transport layer individually or in combination with the following compound.
- an aromatic amine compound for example, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used.
- aromatic amine compound for example, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB), N, N′-bis (3-methylphenyl) -N , N′-diphenyl- [1,1′-biphenyl] -4,4′-diamine (abbreviation: TPD), 4-phenyl-4 ′-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: BAFLP), 4,4′-bis [N- (9,9-dimethylfluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: DFLDPBi), 4,4 ′, 4 ′′ -tris (N, N -Diphenylamino
- the hole-transporting layer includes 4,4′-di (9-carbazolyl) biphenyl (abbreviation: CBP), 9- [4- (9-carbazolyl) phenyl] -10-phenylanthracene (abbreviation: CzPA), 9- Carbazole derivatives such as phenyl-3- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: PCzPA); 2-t-butyl-9,10-di (2-naphthyl) anthracene ( Abbreviations: t-BuDNA), 9,10-di (2-naphthyl) anthracene (abbreviation: DNA), anthracene derivatives such as 9,10-diphenylanthracene (abbreviation: DPAnth); A high molecular compound such as poly (N-vinylcarbazole) (abbreviation: PVK) or poly
- the layer including a compound having a high hole-transport property may be a single layer or a stacked layer including two or more layers including the above compound.
- the hole transport layer may have a two-layer structure of a first hole transport layer (anode side) and a second hole transport layer (light emitting layer side).
- the compound (1) may be contained in either the first hole transport layer or the second hole transport layer.
- the compound (1) is preferably contained in the first hole transport layer, and in another embodiment, the compound (1) is contained in the second hole transport layer. preferable.
- the light emitting layer is a layer including a material having high light emitting property (dopant material), and various materials can be used.
- a fluorescent material or a phosphorescent material can be used as the dopant material.
- the fluorescent light-emitting material is a compound that emits light from a singlet excited state
- the phosphorescent material is a compound that emits light from a triplet excited state.
- pyrene derivatives As a blue fluorescent material that can be used for the light emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, and the like can be used.
- N, N′-bis [4- (9H-carbazol-9-yl) phenyl] -N, N′-diphenylstilbene-4,4′-diamine (abbreviation: YGA2S)
- 4- (9H -Carbazol-9-yl) -4 '-(10-phenyl-9-anthryl) triphenylamine (abbreviation: YGAPA)
- 4- (10-phenyl-9-anthryl) -4'-(9-phenyl-9H -Carbazol-3-yl) triphenylamine abbreviation: PCBAPA
- An aromatic amine derivative or the like can be used as a green fluorescent material that can be used in the light emitting layer.
- Tetracene derivatives, diamine derivatives and the like can be used as red fluorescent materials that can be used for the light emitting layer.
- N, N, N ′, N′-tetrakis (4-methylphenyl) tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N, N, N ′, And N′-tetrakis (4-methylphenyl) acenaphtho [1,2-a] fluoranthene-3,10-diamine (abbreviation: p-mPhAFD).
- a metal complex such as an iridium complex, an osmium complex, or a platinum complex
- a metal complex such as an iridium complex, an osmium complex, or a platinum complex
- a metal complex such as an iridium complex, an osmium complex, or a platinum complex
- a metal complex such as an iridium complex, an osmium complex, or a platinum complex
- a metal complex such as an iridium complex, an osmium complex, or a platinum complex
- FIr6 bis [2- (4 ′ , 6′-difluorophenyl) pyridinato-N, C2 ′] iridium (III) picolinate
- FIrpic bis [2- (3 ′, 5′bistrifluoromethylphenyl) pyridinato-N, C2 ′] iridium (III ) Picolinate (abbreviation: Ir (CF 3 ppy) 2 (
- An iridium complex or the like can be used as a green phosphorescent material that can be used for the light emitting layer.
- red phosphorescent light-emitting material that can be used for the light-emitting layer
- metal complexes such as an iridium complex, a platinum complex, a terbium complex, and a europium complex
- Ir (btp) 2 (acac) bis [2- (2′-benzo [4,5- ⁇ ] thienyl) pyridinato-N, C3 ′] iridium (III) acetylacetonate
- Ir (btp) 2 (acac) bis (1-phenylisoquinolinato-N, C2 ′) iridium (III) acetylacetonate (abbreviation: Ir (piq) 2 (acac))
- Ir (piq) 2 (acac) bis [2,3-bis (4-fluoro Phenyl) quinoxalinato] iridium (III)
- Ir (Fdpq) 2 (acac) 2,3,7,
- tris (acetylacetonate) (monophenanthroline) terbium (III) (abbreviation: Tb (acac) 3 (Phen)
- tris (1,3-diphenyl-1,3-propanedionato) (monophenanthroline) europium (III) (abbreviation: Eu (DBM) 3 (Phen)
- tris [1- (2-thenoyl) -3,3,3-trifluoroacetonato] (monophenanthroline) europium (III) (abbreviation: Eu ( Since rare earth metal complexes such as TTA) 3 (Phen)) emit light from rare earth metal ions (electron transition between different multiplicity), they can be used as phosphorescent materials.
- the light emitting layer may have a configuration in which the above-described dopant material is dispersed in another material (host material).
- the host material the compound (1) and various other materials can be used.
- the lowest unoccupied orbital level (LUMO level) and the highest occupied orbital level (HOMO level) are lower than that of the dopant material. It is preferable to use a material.
- a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex
- (2h) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives
- (3h) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivative
- tris (8-quinolinolato) aluminum (III) (abbreviation: also referred to as Alq 3 or Alq)
- tris (4-methyl-8-quinolinolato) aluminum (III) (abbreviation: Almq 3 )
- bis (10- Hydroxybenzo [h] quinolinato) beryllium (II) (abbreviation: BeBq 2 )
- bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (III) (abbreviation: BAlq)
- bis (8-quinolinolato ) Zinc (II) (abbreviation: Znq)
- bis [2- (2-benzoxazolyl) phenolato] zinc (II) (abbreviation: ZnPBO), bis [2- (2-benzothiazolyl) phenolato] zinc (II)
- a metal complex such as (abbreviation: ZnBTZ); 2- (4-biphenylyl)
- the electron transport layer is a layer containing a material having a high electron transport property (electron transport material).
- a material having a high electron transport property electron transport material
- For the electron transport layer for example, (1e) metal complexes such as aluminum complexes, beryllium complexes, zinc complexes, (2e) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives, (3e) a polymer compound, Can be used.
- metal complex for example, tris (8-quinolinolato) aluminum (III) (abbreviation: Alq), tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq 3 ), bis (10-hydroxybenzo [h] Quinolinato) beryllium (abbreviation: BeBq 2 ), bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (III) (abbreviation: BAlq), bis (8-quinolinolato) zinc (II) (abbreviation: Znq), bis [2- (2-benzoxazolyl) phenolato] zinc (II) (abbreviation: ZnPBO), bis [2- (2-benzothiazolyl) phenolato] zinc (II) (abbreviation: ZnBTZ) .
- heteroaromatic compound for example, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis [5 -(Pt-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 3- (4-tert-butylphenyl) -4-phenyl-5- (4 -Biphenylyl) -1,2,4-triazole (abbreviation: TAZ), 3- (4-tert-butylphenyl) -4- (4-ethylphenyl) -5- (4-biphenylyl) -1,2,4 -Triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), 4,4'-bis (5-methylbenzo
- polymer compound for example, poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF-Py), poly [(9, 9-dioctylfluorene-2,7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy).
- the above materials are mainly materials having an electron mobility of 10 ⁇ 6 cm 2 / Vs or higher. Note that materials other than those described above may be used for the electron-transport layer as long as the material has a higher electron-transport property than the hole-transport property. Further, the electron transport layer is not limited to a single layer, and two or more layers made of the above materials may be stacked. For example, the electron transport layer may have a two-layer structure of a first electron transport layer (light emitting layer side) and a second electron transport layer (cathode side).
- the electron injection layer is a layer containing a material having a high electron injection property.
- a material having a high electron injection property lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), lithium oxide (LiOx), etc.
- Alkali metals, alkaline earth metals, or compounds thereof can be used.
- a material containing an electron transporting property containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a material containing magnesium (Mg) in Alq may be used. In this case, electron injection from the cathode can be performed more efficiently.
- a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer.
- a composite material is excellent in electron injecting property and electron transporting property because the organic compound receives electrons from the electron donor.
- the organic compound is preferably a material excellent in transporting received electrons.
- a material (metal complex, heteroaromatic compound, or the like) constituting the above-described electron transport layer is used. be able to.
- the electron donor may be any material that exhibits an electron donating property with respect to the organic compound.
- alkali metals, alkaline earth metals, and rare earth metals are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like can be given.
- Alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxide, calcium oxide, barium oxide, and the like can be given.
- a Lewis base such as magnesium oxide can also be used.
- an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.
- a cathode material include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg) and calcium (Ca ), Alkaline earth metals such as strontium (Sr), and alloys containing these (for example, rare earth metals such as MgAg, AlLi), europium (Eu), ytterbium (Yb), and alloys containing these.
- the cathode is formed using an alkali metal, an alkaline earth metal, or an alloy containing these.
- a vacuum evaporation method or a sputtering method can be used.
- coating method, the inkjet method, etc. can be used.
- the cathode can be formed using various conductive materials. These conductive materials can be formed by a sputtering method, an inkjet method, a spin coating method, or the like.
- an insulating layer made of an insulating thin film layer may be inserted between the pair of electrodes.
- the material used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, and silicon oxide. Germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, and the like. A mixture or laminate of these may be used.
- the space layer is a fluorescent layer for the purpose of adjusting the carrier balance so that excitons generated in the phosphorescent layer are not diffused into the fluorescent layer. It is a layer provided between the layer and the phosphorescent light emitting layer.
- the space layer can be provided between the plurality of phosphorescent light emitting layers. Since the space layer is provided between the light emitting layers, the material is preferably a material having both electron transporting properties and hole transporting properties. In order to prevent diffusion of triplet energy in the adjacent phosphorescent light emitting layer, the triplet energy is preferably 2.6 eV or more. Examples of the material used for the space layer include the same materials as those used for the above-described hole transport layer.
- a blocking layer such as an electron blocking layer, a hole blocking layer, or a triplet blocking layer may be provided in a portion adjacent to the light emitting layer.
- the electron blocking layer is a layer that prevents electrons from leaking from the light emitting layer to the hole transport layer
- the hole blocking layer is a layer that prevents holes (holes) from leaking from the light emitting layer to the electron transport layer.
- the triplet blocking layer has a function of preventing excitons generated in the light emitting layer from diffusing into surrounding layers and confining the excitons in the light emitting layer.
- the compound (1) can also be preferably used as a material for the electron blocking layer and the triplet blocking layer.
- Each layer of the organic EL element can be formed by a conventionally known vapor deposition method, coating method, or the like.
- the film thickness of each layer is not particularly limited, but in general, if the film thickness is too thin, defects such as pinholes are likely to occur. Conversely, if it is too thick, a high driving voltage is required and the efficiency deteriorates, so 5 nm to 10 ⁇ m is preferable. It is more preferably 0.2 ⁇ m.
- the organic EL element can be used for display devices such as an organic EL panel module, display devices such as a television, a mobile phone, and a personal computer, and electronic equipment such as a light emitting device for lighting and a vehicle lamp.
- display devices such as an organic EL panel module
- display devices such as a television, a mobile phone, and a personal computer
- electronic equipment such as a light emitting device for lighting and a vehicle lamp.
- Phenanthrene-2-boronic acid (11.1 g, 50 mmol), 1-chloro-4-iodobenzene (11.9 g, 50 mmol), tetrakis (synthesized by the method described in WO2009 / 116628 under an argon atmosphere Triphenylphosphine) palladium (0) (1.16 g, 1 mmol), toluene (200 mL), and 2M aqueous sodium carbonate solution (100 mL) were sequentially added, and the mixture was heated to reflux for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene.
- Example 1 A glass substrate with an ITO transparent electrode (length 75 mm ⁇ width 25 mm ⁇ thickness 1.1 mm) (manufactured by Geomatek Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes. The thickness of the ITO transparent electrode was 130 nm.
- the glass substrate with the ITO transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum evaporation apparatus, and the following compound (HI-1) is first formed so as to cover the transparent electrode on the surface where the ITO transparent electrode line is formed. ) was deposited to form a 5 nm thick HI-1 film, and a hole injection layer was formed.
- the following compound HT-1 was vapor-deposited as a first hole transport material on the hole injection layer to form an HT-1 film having a thickness of 80 nm, thereby forming a first hole transport layer.
- the compound H1 was vapor-deposited on the first hole transport layer to form a 10 nm-thick HT-2 film, thereby forming a second hole transport layer.
- compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated to form a co-deposited film having a thickness of 25 nm.
- the concentration of Compound BD-1 was 4.0% by mass. This co-deposited film functions as a light emitting layer.
- the following compound ET-1 was deposited on the light emitting layer to form an ET-1 film having a thickness of 10 nm, thereby forming a first electron transporting layer.
- the following compound ET-2 was deposited on the first electron transport layer to form an ET-2 film having a thickness of 15 nm, thereby forming a second electron transport layer.
- lithium fluoride (LiF) was deposited to form a 1 nm-thick LiF film, thereby forming an electron injecting electrode (cathode).
- metal aluminum (Al) was vapor-deposited on the said LiF film
- Example 2-7 an organic EL device was produced in the same manner as in Example 1 except that the compound H1 which is a material used for the second hole transport layer was changed to the compounds shown in Table 1.
- organic EL elements that can be driven at a low voltage and have a long life can be obtained by using the compounds H1 to H4, H6, and H7. It is considered that the compound of the present invention has a structure represented by the formula (1), so that it is easier to transport holes than existing materials. From this, it is possible to drive at a low voltage, and it is considered that the lifetime performance is improved because the carrier balance of the element is optimized.
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Abstract
Description
特許文献2は、3-フェナントリル基が直接又はリンカーを介して中心窒素原子に結合した三級アミン化合物、例えば、化合物1-1、4-2及び4-3、を記載している。これらの化合物は有機EL素子の正孔注入層、正孔輸送層、発光層、その他の層に使用できることが記載されており、実施例では電子阻止層(EBL:Electron-Blocking Layer)に用いられている。
しかしながら、有機EL素子を低電圧で駆動することを可能にする更なる新規材料の開発が依然として望まれている。
[1]下記式(1)で表される化合物(以下、「化合物(1)」ともいう。)。
R1~R3は、それぞれ独立に、炭素数1~20のアルキル基、環形成炭素数3~50のシクロアルキル基、炭素数1~20のハロアルキル基、炭素数1~20のアルコキシ基、炭素数1~20のハロアルコキシ基、環形成炭素数6~18のアリール基、環形成炭素数6~18のアリールオキシ基、ハロゲン原子及びシアノ基からなる群より選ばれる1種を表す。
R4及びR5は、それぞれ独立に、炭素数1~20のアルキル基、環形成炭素数3~50のシクロアルキル基、炭素数1~20のハロアルキル基、炭素数1~20のアルコキシ基、炭素数1~20のハロアルコキシ基、環形成炭素数6~18のアリール基、環形成炭素数6~18のアリールオキシ基、ハロゲン原子及びシアノ基からなる群より選ばれる1種を表す。
aは0~4の整数であり、bは0~2の整数であり、cは0~3の整数であり、dは0~3の整数であり、eは0~4の整数を表す。(R1)0、(R2)0、(R3)0、(R4)0及び(R5)0は、それぞれ、R1、R2、R3、R4又はR5が存在しないことを意味する。a、b、c、d又はeが2以上の整数を表す場合、2~4個のR1、2個のR2、2又は3個のR3、2又は3個のR4、及び2~4個のR5は、それぞれ同一でも異なっていてもよく、R1~R5から選ばれる隣接する2つの基が互いに結合して環構造を形成することはない。
L1~L3は、それぞれ独立に、単結合、又は置換若しくは無置換の環形成炭素数6~30のアリーレン基を表す。
Arは、置換若しくは無置換の環形成炭素数6~50のアリール基、置換若しくは無置換の環形成原子数5~12のヘテロアリール基、又は環中に含有するヘテロ原子が酸素原子及び硫黄原子から選ばれる少なくとも1種である置換若しくは無置換の環形成原子数13~50のヘテロアリール基を表す。
Xは、酸素原子又は硫黄原子である。
前記「置換若しくは無置換」というときの任意の置換基は、炭素数1~20のアルキル基、環形成炭素数6~18のアリール基、環形成炭素数3~50のシクロアルキル基、環形成炭素数6~18のアリール基を有する炭素数7~30のアラルキル基、炭素数1~20のアルコキシ基、環形成炭素数6~18のアリールオキシ基、炭素数1~20のアルキル基及び環形成炭素数6~18のアリール基から選ばれる置換基を有するモノ置換、ジ置換又はトリ置換シリル基、炭素数1~20のハロアルキル基、炭素数1~20のハロアルコキシ基、ハロゲン原子、シアノ基、並びにニトロ基からなる群より選ばれる1種である。当該任意の置換基が複数存在する場合は、それぞれ同一でも異なっていてもよい。〕
[3]陰極、陽極、及び該陰極と該陽極との間に配置された有機薄膜層を有する有機エレクトロルミネッセンス素子であって、該有機薄膜層は1又は複数の層を含み、該有機薄膜層は発光層を含み、該有機薄膜層の少なくとも1層が上記[1]に記載の化合物(1)を含む、有機エレクトロルミネッセンス素子。
[4]上記[3]に記載の有機エレクトロルミネッセンス素子を備える電子機器。
原子数、炭素数、その他の態様についても、同様に任意に組み合わせることができる。また、前記の基、原子数、炭素数、その他の態様相互の組合せについても同様である。
R1~R3は、それぞれ独立に、炭素数1~20のアルキル基、環形成炭素数3~50のシクロアルキル基、炭素数1~20のハロアルキル基、炭素数1~20のアルコキシ基、炭素数1~20のハロアルコキシ基、環形成炭素数6~18のアリール基、環形成炭素数6~18のアリールオキシ基、ハロゲン原子及びシアノ基からなる群より選ばれる1種を表す。
R4及びR5は、それぞれ独立に、炭素数1~20のアルキル基、環形成炭素数3~50のシクロアルキル基、炭素数1~20のハロアルキル基、炭素数1~20のアルコキシ基、炭素数1~20のハロアルコキシ基、環形成炭素数6~18のアリール基、環形成炭素数6~18のアリールオキシ基、ハロゲン原子及びシアノ基からなる群より選ばれる1種を表す。
aは0~4の整数であり、bは0~2の整数であり、cは0~3の整数であり、dは0~3の整数であり、eは0~4の整数を表す。(R1)0、(R2)0、(R3)0、(R4)0及び(R5)0は、それぞれ、R1、R2、R3、R4又はR5が存在しないことを意味する。a、b、c、d又はeが2以上の整数を表す場合、2~4個のR1、2個のR2、2又は3個のR3、2又は3個のR4、及び2~4個のR5は、それぞれ同一でも異なっていてもよく、R1~R5から選ばれる隣接する2つの基が互いに結合して環構造を形成することはない。
L1~L3は、それぞれ独立に、単結合、又は置換若しくは無置換の環形成炭素数6~30のアリーレン基を表す。
Arは、置換若しくは無置換の環形成炭素数6~50のアリール基、置換若しくは無置換の環形成原子数5~12のヘテロアリール基、又は環中に含有するヘテロ原子が酸素原子及び硫黄原子からなる群より選ばれる少なくとも1種である置換若しくは無置換の環形成原子数13~50のヘテロアリール基を表す。
Xは、酸素原子又は硫黄原子である。
前記「置換若しくは無置換」というときの任意の置換基は、炭素数1~20のアルキル基;環形成炭素数6~18のアリール基;環形成炭素数3~50のシクロアルキル基;環形成炭素数6~18のアリール基を有する炭素数7~30のアラルキル基;炭素数1~20のアルコキシ基;環形成炭素数6~18のアリールオキシ基;炭素数1~20のアルキル基及び環形成炭素数6~18のアリール基から選ばれる置換基を有するモノ置換、ジ置換又はトリ置換シリル基;炭素数1~20のハロアルキル基;炭素数1~20のハロアルコキシ基;ハロゲン原子;シアノ基;並びにニトロ基からなる群より選ばれる1種である。当該任意の置換基が複数存在する場合は、それぞれ同一でも異なっていてもよい。
R1~R3は、それぞれ独立に、好ましくは炭素数1~20のアルキル基、環形成炭素数6~18のアリール基、環形成炭素数6~50のアリールオキシ基、及びシアノ基からなる群より選ばれる1種であり、より好ましくは炭素数1~20のアルキル基、環形成炭素数6~18のアリール基である。
好ましくは、R4及びR5は、それぞれ独立に、炭素数1~20のアルキル基、又は環形成炭素数6~18のアリール基から選ばれる。
該アリール基としては、例えば、フェニル基、ビフェニリル基、ターフェニリル基、ビフェニレニル基、ナフチル基、アセナフチレニル基、アントリル基、ベンゾアントリル基、アセアントリル基、フェナントリル基、ベンゾフェナントリル基、トリフェニレニル基、フェナレニル基、フルオレニル基、ベンゾフルオレニル基、ピレニル基、クリセニル基、s-インダセニル基、as-インダセニル基、及びフルオランテニル基が挙げられ、フェニル基、ビフェニリル基、ターフェニリル基、又はナフチル基が好ましく、フェニル基、ビフェニリル基、又はナフチル基がより好ましく、フェニル基であることが更に好ましい。
bは0~2の整数、好ましくは0又は1である。
cは0~3の整数、好ましくは0~2の整数、より好ましくは0又は1である。
dは0~3の整数、好ましくは0~2の整数、より好ましくは0又は1である。
eは0~4の整数、好ましくは0~2の整数、より好ましくは0又は1である。
a~eのそれぞれが0である場合、すなわち、(R1)0、(R2)0、(R3)0、(R4)0、又は(R5)0とは、それぞれ、R1、R2、R3、R4、又はR5が存在しないこと、すなわち、R1、R2、R3、R4、又はR5で置換されていないことを意味する。
a、b、c、d又はeが2以上の整数を表す場合、2~4個のR1、2個のR2、2又は3個のR3、2又は3個のR4、及び2~4個のR5はそれぞれ同一でも異なっていてもよい。R1~R5から選ばれる隣接する2つの基が互いに結合して環構造を形成することはない。
上記へテロアリール基としては、好ましくは1~5個、より好ましくは1~3個、更に好ましくは1~2個の環形成ヘテロ原子を有するヘテロアリール基が挙げられる。
p、q、r又はsが2以上の整数を表す場合、2~5個、2~4個、2~3個、又は2個のRはそれぞれ同一でも異なっていてもよい。
Ra及びRbが表す各基の詳細は、化合物(1)の「置換若しくは無置換」というときの任意の置換基に関して上記した各基と同様である。
好ましくは、Ra及びRbは、それぞれ独立に、環形成炭素数6~12のアリール基から選ばれ、より好ましくはフェニル基から選ばれる。
式(j)及び(k)において、Yは、窒素原子、酸素原子、又は硫黄原子を表す。Yは好ましくは酸素原子又は硫黄原子、より好ましくは硫黄原子である。
環構造としては、ベンゼン環等の芳香族炭化水素環、又は酸素原子、硫黄原子等の環形成ヘテロ原子を有する芳香族複素環が好ましい。
式(1)で表される化合物の他の態様において、隣接する2つのRは互いに結合していなくてもよい。
各R、Ra及びRbから選ばれる2つが互いに結合して、環構造を形成してもよい。
ただし、式(f)及び(k)~(m)において、隣接する2つのRが互いに結合して、環構造を形成することはない。
式(1)~(5)で表される化合物の他の態様において、式(a)~(o)で表される基上の水素原子がRで置換されていないこと、すなわち、p~tのすべてが0であることが好ましい。
(R)0はRが存在しないことを意味する。
ただし、式(b-1)~(b-3)、(c-1)~(c-3)、(d-1)~(d-3)、(e-1)、(f)、(g-1)、(i-1)、(i-2)、(l-1)、(l-2)、(m-1)及び(m-2)において、隣接する2つのRが互いに結合して、環構造を形成することはない。
また、式(1)~(5)で表される化合物の一態様において、L3が好ましくは単結合である。
また、式(1)~(5)で表される化合物の一態様において、L2が好ましくは置換若しくは無置換の環形成炭素数6~30、より好ましくは6~24、更に好ましくは6~12のアリーレン基である。
L1が式(ii)又は(iii)で表される場合、*と**の一方は前記式(1)~(5)中のArとの結合を表し、他方は前記式(1)~(5)中の窒素原子との結合を表す。
L2が式(ii)又は(iii)で表される場合、*と**の一方は前記式(1)~(5)中のジベンゾフラン環又はジベンゾチオフェン環との結合を表し、他方は前記式(1)~(5)中の窒素原子との結合を表し、
L3が式(ii)又は(iii)で表される場合、*と**の一方は前記式(1)~(5)中の2-フェナントリル基との結合を表し、他方は前記式(1)~(5)中の窒素原子との結合を表す。
Arが、前記式(b-1)、(b-2)、(c-1)、又は(g-1)で表される基であり、L1が単結合であり、L2及びL3が前記式(ii)で表される基である、式(2)又は式(3)の化合物;
Arが、前記式(d-2)、(e-1)、(l-1)、(l-2)、(m-1)、又は(m-2)で表される基であり、L1及びL2が前記式(ii)で表される基であり、L3が単結合で表される基である、式(2)又は式(3)の化合物;
Arが、前記式(b-1)又は(c-1)で表される基であり、L1及びL2が前記式(ii)で表される基であり、L3が単結合で表される基である、式(4)又は式(5)の化合物;及び
Arが、前記式(b-1)又は(c-1)で表される基であり、L1及びL3が単結合であり、L2が前記式(ii)で表される基であり、R4がフェニル基であり、R5がフェニル基又はビフェニル基であり、dが0又は1であり、eが1である、式(2)又は式(3)の化合物;からなる群より選ばれる1種である。
本発明の一態様である有機EL素子用材料は、前記式(1)で表される化合物(化合物(1))を含み、前記式(2)~(5)で表される化合物からなる群より選ばれる少なくとも1種を含むことが好ましい。
なお、以下の説明において、化合物(1)に関する記載は、化合物(1)、それに包含される前記式(2)~(5)で表される化合物、並びにそれに包含される下位概念の前記各化合物に置き換えて読むことができる。
本発明の一態様である有機EL素子用材料における化合物(1)の含有量は、特に制限されず、例えば、1質量%以上(100質量%を含む)であればよく、10質量%以上(100質量%を含む)であることが好ましく、50質量%以上(100質量%を含む)であることがより好ましく、80質量%以上(100質量%を含む)であることが更に好ましく、90質量%以上(100質量%を含む)であることがより更に好ましい。
本発明の一態様である有機EL素子用材料は、有機EL素子製造用の材料として有用であり、例えば、蛍光発光ユニットの発光層におけるホスト材料及びドーパント材料や、燐光発光ユニットの発光層におけるホスト材料として用いることができる。また、蛍光発光ユニット及び燐光発光ユニットのいずれにおいても、陽極と発光層との間に設けられる正孔輸送層、正孔注入層、電子阻止層等の陽極側有機薄膜層、及び陰極と発光層との間に設けられる電子輸送層、電子注入層、正孔阻止層等の陰極側有機薄膜層の材料としても有用である。前記陽極側有機薄膜層は2以上の層を含む多層であってもよく、該2以上の層は正孔輸送層であってもよい。本発明の有機EL素子用材料は、該2以上の正孔輸送層のいずれの層に含まれていてもよい。すなわち、本発明の有機EL素子用材料は、発光層に最も近接する正孔輸送層、陽極に最も近接する正孔輸送層、及び中間に位置する正孔輸送層のいずれに用いてもよい。
次に、本発明の一態様である有機EL素子について説明する。
有機EL素子は、陰極と陽極との間に1以上の層を含む有機薄膜層を有する。この有機薄膜層は発光層を含み、有機薄膜層の少なくとも一層が化合物(1)を含む。
前記化合物(1)が含まれる有機薄膜層の例としては、陽極と発光層との間に設けられる陽極側有機薄膜層(正孔輸送層、正孔注入層、電子阻止層、励起子阻止層等)、発光層、スペース層、阻止層等が挙げられるが、これらに限定されるものではない。例えば、蛍光発光ユニットの発光層におけるホスト材料やドーパント材料、正孔注入層材料、正孔輸送層材料として用いることができる。また、燐光発光ユニットの発光層におけるホスト材料、正孔注入層材料、正孔輸送層材料として用いることができる。前記陽極側有機薄膜層が2以上の正孔輸送層を含む場合、前記化合物(1)は、いずれの正孔輸送層に含まれていてもよい。すなわち、前記化合物(1)は、発光層に最も近接する正孔輸送層、陽極に最も近接する正孔輸送層、及び中間に位置する正孔輸送層のいずれに含まれていてもよい。
(I)陽極/発光ユニット/陰極
また、上記発光ユニットは、燐光発光層や蛍光発光層を複数有する積層型であってもよく、その場合、各発光層の間に、燐光発光層で生成された励起子が蛍光発光層に拡散することを防ぐ目的で、スペース層を有していてもよい。シンプル型発光ユニットの代表的な層構成を以下に示す。括弧内の層は任意である。
(au)(正孔注入層/)正孔輸送層/蛍光発光層(/電子輸送層)
(bu)(正孔注入層/)正孔輸送層/燐光発光層(/電子輸送層)
(cu)(正孔注入層/)正孔輸送層/第1蛍光発光層/第2蛍光発光層(/電子輸送層)
(du)(正孔注入層/)正孔輸送層/第1燐光発光層/第2燐光発光層(/電子輸送層)
(eu)(正孔注入層/)正孔輸送層/燐光発光層/スペース層/蛍光発光層(/電子輸送層)
(fu)(正孔注入層/)正孔輸送層/第1燐光発光層/第2燐光発光層/スペース層/蛍光発光層(/電子輸送層)
(gu)(正孔注入層/)正孔輸送層/第1燐光発光層/スペース層/第2燐光発光層/スペース層/蛍光発光層(/電子輸送層)
(hu)(正孔注入層/)正孔輸送層/燐光発光層/スペース層/第1蛍光発光層/第2蛍光発光層(/電子輸送層)
(iu)(正孔注入層/)正孔輸送層/電子阻止層/蛍光発光層(/電子輸送層)
(ju)(正孔注入層/)正孔輸送層/電子阻止層/燐光発光層(/電子輸送層)
(ku)(正孔注入層/)正孔輸送層/励起子阻止層/蛍光発光層(/電子輸送層)
(lu)(正孔注入層/)正孔輸送層/励起子阻止層/燐光発光層(/電子輸送層)
(mu)(正孔注入層/)第1正孔輸送層/第2正孔輸送層/蛍光発光層(/電子輸送層)
(nu)(正孔注入層/)第1正孔輸送層/第2正孔輸送層/燐光発光層(/電子輸送層)
(ou)(正孔注入層/)正孔輸送層/蛍光発光層/正孔阻止層(/電子輸送層)
(pu)(正孔注入層/)正孔輸送層/蛍光発光層/トリプレット阻止層(/電子輸送層)
なお、各発光層と正孔輸送層あるいはスペース層との間には、適宜、電子障壁層を設けてもよい。また、各発光層と電子輸送層との間には、適宜、正孔障壁層を設けてもよい。電子障壁層や正孔障壁層を設けることで、電子又は正孔を発光層内に閉じ込めて、発光層における電荷の再結合確率を高め、発光効率を向上させることができる。
(II)陽極/第1発光ユニット/中間層/第2発光ユニット/陰極
ここで、上記第1発光ユニット及び第2発光ユニットとしては、例えば、それぞれ独立に上述のシンプル型発光ユニットの一例として挙げた各発光ユニットから選択することができる。
上記中間層は、一般的に、中間電極、中間導電層、電荷発生層、電子引抜層、接続層、中間絶縁層とも呼ばれ、第1発光ユニットに電子を、第2発光ユニットに正孔を供給する、公知の材料構成を用いることができる。
基板は、有機EL素子の支持体として用いられる。基板としては、例えば、ガラス、石英、プラスチック等の板を用いることができる。また、可撓性基板を用いてもよい。可撓性基板とは、折り曲げることができる(フレキシブル)基板のことであり、例えば、ポリカーボネート、ポリアリレート、ポリエーテルスルフォン、ポリプロピレン、ポリエステル、ポリフッ化ビニル、ポリ塩化ビニルからなるプラスチック基板等が挙げられる。また、無機蒸着フィルムを用いることもできる。
基板上に形成される陽極には、仕事関数の大きい(具体的には4.0eV以上)金属、合金、電気伝導性化合物、及びこれらの混合物等を用いることが好ましい。具体的には、例えば、酸化インジウム-酸化スズ(ITO:Indium Tin Oxide)、珪素若しくは酸化珪素を含有した酸化インジウム-酸化スズ、酸化インジウム-酸化亜鉛、酸化タングステン及び酸化亜鉛を含有した酸化インジウム、グラフェン等が挙げられる。この他、金(Au)、白金(Pt)、ニッケル(Ni)、タングステン(W)、クロム(Cr)、モリブデン(Mo)、鉄(Fe)、コバルト(Co)、銅(Cu)、パラジウム(Pd)、チタン(Ti)、又は前記金属の窒化物(例えば、窒化チタン)等が挙げられる。
仕事関数の小さい材料である、元素周期表の第1族又は第2族に属する元素、すなわち、リチウム(Li)やセシウム(Cs)等のアルカリ金属、及びマグネシウム(Mg)、カルシウム(Ca)、ストロンチウム(Sr)等のアルカリ土類金属、及びこれらを含む合金(例えば、MgAg、AlLi)、ユーロピウム(Eu)、イッテルビウム(Yb)等の希土類金属及びこれらを含む合金等を用いることもできる。なお、アルカリ金属、アルカリ土類金属、及びこれらを含む合金を用いて陽極を形成する場合には、真空蒸着法やスパッタリング法を用いることができる。更に、銀ペースト等を用いる場合には、塗布法やインクジェット法等を用いることができる。
正孔注入層は、正孔注入性の高い材料(正孔注入性材料)を含む層である。本発明の前記化合物を単独又は下記の材料と組み合わせて正孔注入層に用いてもよい。
R27としては、例えば、メチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、イソブチル基、t-ブチル基、シクロペンチル基、シクロヘキシル基等が挙げられる。
正孔輸送層は、正孔輸送性の高い材料(正孔輸送性材料)を含む層である。前記化合物(1)を単独又は下記の化合物と組み合わせて正孔輸送層に用いてもよい。
ただし、電子輸送性よりも正孔輸送性の方が高い化合物であれば、上記以外の化合物を用いてもよい。なお、正孔輸送性の高い化合物を含む層は、単層でもよく、上記化合物を含む2以上の層からなる積層でもよい。例えば、正孔輸送層は第1正孔輸送層(陽極側)と第2正孔輸送層(発光層側)の2層構造にしてもよい。この場合、前記化合物(1)は第1正孔輸送層及び第2正孔輸送層のいずれに含まれていてもよい。本発明の一態様においては、前記化合物(1)が第1正孔輸送層に含まれるのが好ましく、他の態様においては、前記化合物(1)が第2正孔輸送層に含まれるのが好ましい。
発光層は、発光性の高い材料(ドーパント材料)を含む層であり、種々の材料を用いることができる。例えば、蛍光発光材料や燐光発光材料をドーパント材料として用いることができる。蛍光発光材料は一重項励起状態から発光する化合物であり、燐光発光材料は三重項励起状態から発光する化合物である。
発光層としては、上述したドーパント材料を他の材料(ホスト材料)に分散させた構成としてもよい。ホスト材料としては、前記化合物(1)、その他各種のものを用いることができ、ドーパント材料よりも最低空軌道準位(LUMO準位)が高く、最高占有軌道準位(HOMO準位)が低い材料を用いることが好ましい。
(1h)アルミニウム錯体、ベリリウム錯体、又は亜鉛錯体等の金属錯体、
(2h)オキサジアゾール誘導体、ベンゾイミダゾール誘導体、又はフェナントロリン誘導体等の複素環化合物、
(3h)カルバゾール誘導体、アントラセン誘導体、フェナントレン誘導体、ピレン誘導体、又はクリセン誘導体等の縮合芳香族化合物、
(4h)トリアリールアミン誘導体又は縮合多環芳香族アミン誘導体等の芳香族アミン化合物、
を使用することができる。
2-(4-ビフェニリル)-5-(4-tert-ブチルフェニル)-1,3,4-オキサジアゾール(略称:PBD)、1,3-ビス[5-(p-tert-ブチルフェニル)-1,3,4-オキサジアゾール-2-イル]ベンゼン(略称:OXD-7)、3-(4-ビフェニリル)-4-フェニル-5-(4-tert-ブチルフェニル)-1,2,4-トリアゾール(略称:TAZ)、2,2’,2’’-(1,3,5-ベンゼントリイル)トリス(1-フェニル-1H-ベンゾイミダゾール)(略称:TPBI)、バソフェナントロリン(略称:BPhen)、バソキュプロイン(略称:BCP)等の複素環化合物;
9-[4-(10-フェニル-9-アントリル)フェニル]-9H-カルバゾール(略称:CzPA)、3,6-ジフェニル-9-[4-(10-フェニル-9-アントリル)フェニル]-9H-カルバゾール(略称:DPCzPA)、9,10-ビス(3,5-ジフェニルフェニル)アントラセン(略称:DPPA)、9,10-ジ(2-ナフチル)アントラセン(略称:DNA)、2-tert-ブチル-9,10-ジ(2-ナフチル)アントラセン(略称:t-BuDNA)、9,9’-ビアントリル(略称:BANT)、9,9’-(スチルベン-3,3’-ジイル)ジフェナントレン(略称:DPNS)、9,9’-(スチルベン-4,4’-ジイル)ジフェナントレン(略称:DPNS2)、3,3’,3’’-(ベンゼン-1,3,5-トリイル)トリピレン(略称:TPB3)、9,10-ジフェニルアントラセン(略称:DPAnth)、6,12-ジメトキシ-5,11-ジフェニルクリセン等の縮合芳香族化合物;及び
N,N-ジフェニル-9-[4-(10-フェニル-9-アントリル)フェニル]-9H-カルバゾール-3-アミン(略称:CzA1PA)、4-(10-フェニル-9-アントリル)トリフェニルアミン(略称:DPhPA)、N,9-ジフェニル-N-[4-(10-フェニル-9-アントリル)フェニル]-9H-カルバゾール-3-アミン(略称:PCAPA)、N,9-ジフェニル-N-{4-[4-(10-フェニル-9-アントリル)フェニル]フェニル}-9H-カルバゾール-3-アミン(略称:PCAPBA)、N-(9,10-ジフェニル-2-アントリル)-N,9-ジフェニル-9H-カルバゾール-3-アミン(略称:2PCAPA)、4,4’-ビス[N-(1-ナフチル)-N-フェニルアミノ]ビフェニル(略称:NPB又はα-NPD)、N,N’-ビス(3-メチルフェニル)-N,N’-ジフェニル-[1,1’-ビフェニル]-4,4’-ジアミン(略称:TPD)、4,4’-ビス[N-(9,9-ジメチルフルオレン-2-イル)-N-フェニルアミノ]ビフェニル(略称:DFLDPBi)、4,4’-ビス[N-(スピロ-9,9’-ビフルオレン-2-イル)-N-フェニルアミノ]ビフェニル(略称:BSPB)等の芳香族アミン化合物;を用いることができる。これらのホスト材料は1種、又は複数種用いてもよい。
電子輸送層は電子輸送性の高い材料(電子輸送性材料)を含む層である。電子輸送層には、例えば、
(1e)アルミニウム錯体、ベリリウム錯体、亜鉛錯体等の金属錯体、
(2e)イミダゾール誘導体、ベンゾイミダゾール誘導体、アジン誘導体、カルバゾール誘導体、フェナントロリン誘導体等の複素芳香族化合物、
(3e)高分子化合物、
を使用することができる。
電子注入層は、電子注入性の高い材料を含む層である。電子注入層には、リチウム(Li)、セシウム(Cs)、カルシウム(Ca)、フッ化リチウム(LiF)、フッ化セシウム(CsF)、フッ化カルシウム(CaF2)、リチウム酸化物(LiOx)等のアルカリ金属、アルカリ土類金属、又はそれらの化合物を用いることができる。その他、電子輸送性を有する材料にアルカリ金属、アルカリ土類金属、又はそれらの化合物を含有させたもの、具体的にはAlq中にマグネシウム(Mg)を含有させたもの等を用いてもよい。なお、この場合には、陰極からの電子注入をより効率良く行うことができる。
あるいは、電子注入層に、有機化合物と電子供与体(ドナー)とを混合してなる複合材料を用いてもよい。このような複合材料は、有機化合物が電子供与体から電子を受け取るため、電子注入性及び電子輸送性に優れている。この場合、有機化合物としては、受け取った電子の輸送に優れた材料であることが好ましく、具体的には、例えば上述した電子輸送層を構成する材料(金属錯体や複素芳香族化合物等)を用いることができる。電子供与体としては、有機化合物に対し電子供与性を示す材料であればよい。具体的には、アルカリ金属、アルカリ土類金属及び希土類金属が好ましく、リチウム、セシウム、マグネシウム、カルシウム、エルビウム、イッテルビウム等が挙げられる。また、アルカリ金属酸化物やアルカリ土類金属酸化物が好ましく、リチウム酸化物、カルシウム酸化物、バリウム酸化物等が挙げられる。また、酸化マグネシウムのようなルイス塩基を用いることもできる。また、テトラチアフルバレン(略称:TTF)等の有機化合物を用いることもできる。
陰極には、仕事関数の小さい(具体的には3.8eV以下)金属、合金、電気伝導性化合物、及びこれらの混合物等を用いることが好ましい。このような陰極材料の具体例としては、元素周期表の第1族又は第2族に属する元素、すなわちリチウム(Li)やセシウム(Cs)等のアルカリ金属、及びマグネシウム(Mg)、カルシウム(Ca)、ストロンチウム(Sr)等のアルカリ土類金属、及びこれらを含む合金(例えば、MgAg、AlLi)、ユーロピウム(Eu)、イッテルビウム(Yb)等の希土類金属及びこれらを含む合金等が挙げられる。
なお、アルカリ金属、アルカリ土類金属、これらを含む合金を用いて陰極を形成する場合には、真空蒸着法やスパッタリング法を用いることができる。また、銀ペースト等を用いる場合には、塗布法やインクジェット法等を用いることができる。
なお、電子注入層を設けることにより、仕事関数の大小に関わらず、アルミニウム(Al)、銀(Ag)、酸化インジウム錫合金(ITO)、グラフェン、珪素若しくは酸化珪素を含有した酸化インジウム-酸化スズ等様々な導電性材料を用いて陰極を形成することができる。これらの導電性材料は、スパッタリング法やインクジェット法、スピンコート法等を用いて成膜することができる。
有機EL素子は、超薄膜に電界を印加するために、リークやショートによる画素欠陥が生じやすい。これを防止するために、一対の電極間に絶縁性の薄膜層からなる絶縁層を挿入してもよい。
絶縁層に用いられる材料としては、例えば、酸化アルミニウム、フッ化リチウム、酸化リチウム、フッ化セシウム、酸化セシウム、酸化マグネシウム、フッ化マグネシウム、酸化カルシウム、フッ化カルシウム、窒化アルミニウム、酸化チタン、酸化珪素、酸化ゲルマニウム、窒化珪素、窒化ホウ素、酸化モリブデン、酸化ルテニウム、酸化バナジウム等が挙げられる。なお、これらの混合物や積層物を用いてもよい。
上記スペース層とは、例えば、蛍光発光層と燐光発光層とを積層する場合に、燐光発光層で生成する励起子を蛍光発光層に拡散させない、あるいは、キャリアバランスを調整する目的で、蛍光発光層と燐光発光層との間に設けられる層である。また、スペース層は、複数の燐光発光層の間に設けることもできる。
スペース層は発光層間に設けられるため、電子輸送性及び正孔輸送性を兼ね備える材料であることが好ましい。また、隣接する燐光発光層内の三重項エネルギーの拡散を防ぐため、三重項エネルギーが2.6eV以上であることが好ましい。スペース層に用いられる材料としては、上述の正孔輸送層に用いられるものと同様のものが挙げられる。
発光層に隣接する部分に、電子阻止層、正孔阻止層、トリプレット阻止層等の阻止層を設けてもいい。電子阻止層とは発光層から正孔輸送層へ電子が漏れることを防ぐ層であり、正孔阻止層とは発光層から電子輸送層へ正孔(ホール)が漏れることを防ぐ層である。トリプレット阻止層は発光層で生成した励起子が周辺の層へ拡散することを防止し、励起子を発光層内に閉じ込める機能を有する。前記化合物(1)は、電子阻止層及びトリプレット阻止層の材料としても好ましく用いることができる。
室温まで反応液を冷却した後、不溶物を濾過して除き、有機溶媒を減圧下留去した。得られた残渣をシリカゲルカラムクロマトグラフィーにて精製し、化合物H1(4.31g、収率65%)を得た。
LC-MS:calcd for C50H33NO=663、
found m/z=663
室温まで反応液を冷却した後、不溶物を濾過して除き、有機溶媒を減圧下留去した。得られた残渣をシリカゲルカラムクロマトグラフィーにて精製し、化合物H2(5.26g、収率70%)を得た。
LC-MS:calcd for C57H37NO=751、
found m/z=751
室温まで冷却後、反応溶液をトルエンで抽出した。水層を除去し、有機層を水、飽和食塩水で順次洗浄した後、硫酸マグネシウムで乾燥させた。硫酸マグネシウムを濾別後、有機層を濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーにて精製し、化合物A2(12.9g、収率89%)を得た。
室温まで反応液を冷却した後、不溶物を濾過して除き、有機溶媒を減圧下留去した。得られた残渣をシリカゲルカラムクロマトグラフィーにて精製し、化合物H3(3.65g、収率55%)を得た。
LC-MS:calcd for C50H33NO=663、
found m/z=663
室温まで反応液を冷却した後、不溶物を濾過して除き、有機溶媒を減圧下留去した。得られた残渣をシリカゲルカラムクロマトグラフィーにて精製し、化合物H4(2.51g、収率40%)を得た。
LC-MS:calcd for C46H29NS=627、
found m/z=627
室温まで反応液を冷却した後、不溶物を濾過して除き、有機溶媒を減圧下留去した。得られた残渣をシリカゲルカラムクロマトグラフィーにて精製し、化合物H5(3.39g、収率50%)を得た。
LC-MS:calcd for C51H35NO=677、
found m/z=677
化合物H6について、FD-MS分析により構造を同定した。
FD-MS:calcd for C50H33NO=587、
found m/z=587
化合物H7について、FD-MS分析により構造を同定した。
FD-MS:calcd for C50H33NO=763、
found m/z=763
実施例1
縦75mm×横25mm×厚さ1.1mmのITO透明電極付きガラス基板(ジオマテック株式会社製)をイソプロピルアルコール中で超音波洗浄を5分間行なった後、UVオゾン洗浄を30分間行った。ITO透明電極の厚さは130nmとした。
洗浄後のITO透明電極ライン付きガラス基板を真空蒸着装置の基板ホルダーに装着し、まずITO透明電極ラインが形成されている側の面上に前記透明電極を覆うようにして下記化合物(HI-1)を蒸着して膜厚5nmのHI-1膜を成膜し、正孔注入層を形成した。
次に、当該正孔注入層上に、第1正孔輸送材料として下記化合物HT-1を蒸着して膜厚80nmのHT-1膜を成膜し、第1正孔輸送層を形成した。
次に、当該第1正孔輸送層上に、前記化合物H1を蒸着して膜厚10nmのHT-2膜を成膜し、第2正孔輸送層を形成した。
次に、当該第2正孔輸送層上に、化合物BH-1(ホスト材料)と化合物BD-1(ドーパント材料)とを共蒸着し、膜厚25nmの共蒸着膜を成膜した。化合物BD-1の濃度は4.0質量%であった。この共蒸着膜は発光層として機能する。
次に、当該発光層の上に、下記化合物ET-1を蒸着して膜厚10nmのET-1膜を成膜し、第1電子輸送層を形成した。
次に、当該第1電子輸送層の上に、下記化合物ET-2を蒸着して膜厚15nmのET-2膜を成膜し、第2電子輸送層を形成した。
次に、当該第2電子輸送層上に、フッ化リチウム(LiF)を蒸着して膜厚1nmのLiF膜を成膜し、電子注入性電極(陰極)を形成した。
そして、当該LiF膜上に金属アルミニウム(Al)を蒸着して膜厚80nmの金属Al膜を成膜し、金属Al陰極を形成した。
実施例1において、第2正孔輸送層に用いる材料である前記化合物H1を表1に記載の各化合物とした以外は、実施例1と同様にして有機EL素子を作製した。
各実施例及び各比較例で作製した有機EL素子について、電流密度が10mA/cm2となるように電圧を印加し、駆動電圧を測定した。また、電流密度50mA/cm2において駆動した際に、発光輝度が初期輝度の90%となるまでの時間(輝度90%寿命)の評価を実施した。結果を表1に示す。
本発明の化合物は、式(1)で表される構造であることで、既存の材料よりも正孔をより輸送しやすくなったと考えられる。このことから低電圧での駆動が可能となり、また、素子のキャリアバランスが適正化することから寿命性能も向上したと考えられる。
2 基板
3 陽極
4 陰極
5 発光層
6 陽極側有機薄膜層
7 陰極側有機薄膜層
10 発光ユニット
Claims (27)
- 下記式(1)で表される化合物。
〔式(1)中、
R1~R3は、それぞれ独立に、炭素数1~20のアルキル基、環形成炭素数3~50のシクロアルキル基、炭素数1~20のハロアルキル基、炭素数1~20のアルコキシ基、炭素数1~20のハロアルコキシ基、環形成炭素数6~18のアリール基、環形成炭素数6~18のアリールオキシ基、ハロゲン原子及びシアノ基からなる群より選ばれる1種を表す。
R4及びR5は、それぞれ独立に、炭素数1~20のアルキル基、環形成炭素数3~50のシクロアルキル基、炭素数1~20のハロアルキル基、炭素数1~20のアルコキシ基、炭素数1~20のハロアルコキシ基、環形成炭素数6~18のアリール基、環形成炭素数6~18のアリールオキシ基、ハロゲン原子及びシアノ基からなる群より選ばれる1種を表す。
aは0~4の整数であり、bは0~2の整数であり、cは0~3の整数であり、dは0~3の整数であり、eは0~4の整数を表す。(R1)0、(R2)0、(R3)0、(R4)0及び(R5)0は、それぞれ、R1、R2、R3、R4又はR5が存在しないことを意味する。a、b、c、d又はeが2以上の整数を表す場合、2~4個のR1、2個のR2、2又は3個のR3、2又は3個のR4、及び2~4個のR5は、それぞれ同一でも異なっていてもよく、R1~R5から選ばれる隣接する2つの基が互いに結合して環構造を形成することはない。
L1~L3は、それぞれ独立に、単結合、又は置換若しくは無置換の環形成炭素数6~30のアリーレン基を表す。
Arは、置換若しくは無置換の環形成炭素数6~50のアリール基、置換若しくは無置換の環形成原子数5~12のヘテロアリール基、又は環中に含有するヘテロ原子が酸素原子及び硫黄原子からなる群より選ばれる少なくとも1種である置換若しくは無置換の環形成原子数13~50のヘテロアリール基を表す。
Xは、酸素原子又は硫黄原子である。
前記「置換若しくは無置換」というときの任意の置換基は、炭素数1~20のアルキル基、環形成炭素数6~18のアリール基、環形成炭素数3~50のシクロアルキル基、環形成炭素数6~18のアリール基を有する炭素数7~30のアラルキル基、炭素数1~20のアルコキシ基、環形成炭素数6~18のアリールオキシ基、炭素数1~20のアルキル基及び環形成炭素数6~18のアリール基から選ばれる置換基を有するモノ置換、ジ置換又はトリ置換シリル基、炭素数1~20のハロアルキル基、炭素数1~20のハロアルコキシ基、ハロゲン原子、シアノ基、並びにニトロ基からなる群より選ばれる1種である。当該任意の置換基が複数存在する場合は、それぞれ同一でも異なっていてもよい。〕 - Arにおいて、環形成炭素数6~50のアリール基は、フェニル基、ビフェニリル基、ターフェニリル基、ビフェニレニル基、ナフチル基、アセナフチレニル基、アントリル基、ベンゾアントリル基、アセアントリル基、2-フェナントリル基、ベンゾフェナントリル基、フェナレニル基、フルオレニル基、ペンタセニル基、ピセニル基、ペンタフェニル基、ピレニル基、クリセニル基、ベンゾクリセニル基、s-インダセニル基、as-インダセニル基、フルオランテニル基、及びペリレニル基からなる群より選ばれる1種である、請求項1~5のいずれか1項に記載の化合物。
- Arにおいて、環形成原子数5~12のヘテロアリール基は、ピロリル基、フリル基、チエニル基、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、トリアジニル基、イミダゾリル基、オキサゾリル基、チアゾリル基、ピラゾリル基、イソオキサゾリル基、イソチアゾリル基、オキサジアゾリル基、チアジアゾリル基、トリアゾリル基、インドリル基、イソインドリル基、ベンゾフラニル基、イソベンゾフラニル基、ベンゾチオフェニル基、インドリジニル基、キノリジニル基、キノリル基、イソキノリル基、シンノリル基、フタラジニル基、キナゾリニル基、キノキサリニル基、ベンゾイミダゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、インダゾリル基、ベンゾイソキサゾリル基、及びベンゾイソチアゾリル基からなる群より選ばれる1種である、請求項1~5のいずれか1項に記載の化合物。
- Arにおいて、ヘテロ原子が酸素原子又は硫黄原子である環形成原子数13~50のヘテロアリール基は、ジベンゾフラニル基、ナフトベンゾフラニル基、ジベンゾチオフェニル基、ナフトベンゾチオフェニル基、フェノキサジニル基、及びキサンテニル基からなる群より選ばれる1種である、請求項1~5のいずれか1項に記載の化合物。
- Arが下記式(a)~(m)からなる群より選ばれる1種で表される請求項1~8のいずれか1項に記載の化合物。
〔式(a)~(m)において、
*は、前記式(1)中のL1との結合を表す。
各Rは、それぞれ独立に、炭素数1~20のアルキル基、環形成炭素数6~18のアリール基、環形成炭素数3~50のシクロアルキル基、環形成炭素数6~18のアリール基を有する炭素数7~30のアラルキル基、炭素数1~20のアルコキシ基、環形成炭素数6~18のアリールオキシ基、炭素数1~20のアルキル基及び環形成炭素数6~18のアリール基から選ばれる置換基を有するモノ置換、ジ置換又はトリ置換シリル基、炭素数1~20のハロアルキル基、炭素数1~20のハロアルコキシ基、ハロゲン原子、シアノ基、並びにニトロ基からなる群より選ばれる1種の基を表す。
各pはそれぞれ独立に0~5の整数、各qはそれぞれ独立に0~4の整数、rはそれぞれ独立に0~3の整数、sはそれぞれ独立に0~2の整数、tはそれぞれ独立に0又は1を表す。(R)0はRが存在しないことを意味する。p、q、r又はsが2以上の整数を表す場合、2~5個、2~4個、2~3個、又は2個のRはそれぞれ同一でも異なっていてもよい。
式(g)において、Ra及びRbは、それぞれ独立に、炭素数1~20のアルキル基、環形成炭素数6~18のアリール基、環形成炭素数3~50のシクロアルキル基、環形成炭素数6~18のアリール基を有する炭素数7~30のアラルキル基、炭素数1~20のアルコキシ基、環形成炭素数6~18のアリールオキシ基、炭素数1~20のアルキル基及び環形成炭素数6~18のアリール基から選ばれる置換基を有するモノ置換、ジ置換又はトリ置換シリル基、炭素数1~20のハロアルキル基、炭素数1~20のハロアルコキシ基、ハロゲン原子、シアノ基、並びにニトロ基からなる群より選ばれる1種の基を表す。
式(j)及び(k)において、Yは、窒素原子、酸素原子、又は硫黄原子を表す。
式(a)~(e)及び(h)~(j)において、隣接する2つのRは互いに結合して、環構造を形成してもよく、また、式(g)において、各R、Ra及びRbから選ばれる2つが互いに結合して、環構造を形成してもよい。式(f)及び(k)~(m)において、隣接する2つのRが互いに結合して、環構造を形成することはない。〕 - Arで表される構造が、下記式(b-1)、(b-2)、(b-3)、(c-1)、(c-2)、(c-3)、(d-1)、(d-2)、(d-3)、(e-1)、(f)、(g-1)、(i-1)、(i-2)、(l-1)、(l-2)、(m-1)、又は(m-2)で表される請求項1~8のいずれか1項に記載の化合物。
〔式(b-1)、(b-2)、(b-3)、(c-1)、(c-2)、(c-3)、(d-1)、(d-2)、(d-3)、(e-1)、(f)、(g-1)、(i-1)、(i-2)、(l-1)、(l-2)、(m-1)及び(m-2)において、R、p、q、r、s及び*は前記式(a)~(m)に関して定義したとおりである。
(R)0はRが存在しないことを意味する。p、q、r又はsが2以上の整数を表す場合、2~5個、2~4個、2~3個、又は2個のRはそれぞれ同一でも異なっていてもよい。
ただし、当該各式において、隣接する2つのRが互いに結合して、環構造を形成することはない。〕 - L1~L3において、環形成炭素数6~30のアリーレン基が、フェニル基、ビフェニリル基、ターフェニリル基、ビフェニレニル基、ナフチル基、アセナフチレニル基、アントリル基、ベンゾアントリル基、アセアントリル基、2-フェナントリル基、ベンゾフェナントリル基、トリフェニレニル基、フェナレニル基、フルオレニル基、ベンゾフルオレニル基、9,9’-スピロビフルオレニル基、ペンタセニル基、ピセニル基、ペンタフェニル基、ピレニル基、クリセニル基、ベンゾクリセニル基、s-インダセニル基、as-インダセニル基、フルオランテニル基、及びペリレニル基から1個の水素原子を除いて得られる2価の基からなる群より選ばれる1種である、請求項1~10のいずれか1項に記載の化合物。
- L1~L3が、それぞれ独立に、単結合又は下記式(ii)及び(iii)のいずれかで表されるアリーレン基である請求項1~11のいずれか1項に記載の化合物。
〔式(ii)及び(iii)中、Rとqは式(a)~(m)に関して定義したとおりであり、L1が式(ii)又は(iii)で表される場合、**と***の一方は前記式(1)中のArとの結合を表し、他方は前記式(1)中の窒素原子との結合を表す。L2が式(ii)又は(iii)で表される場合、**と***の一方は前記式(1)中のジベンゾフラン環又はジベンゾチオフェン環との結合を表し、他方は前記式(1)中の窒素原子との結合を表す。L3が式(ii)又は(iii)で表される場合、**と***の一方は前記式(1)中の2-フェナントリル基との結合を表し、他方は前記式(1)中の窒素原子との結合を表す。〕 - L3が単結合である請求項1~12のいずれか1項に記載の化合物。
- Arが、前記式(b-1)、(b-2)、(b-3)、(c-1)、(c-2)、(c-3)、(d-1)、(d-3)、(f)、(g-1)、(i-1)、又は(i-2)で表される基であり、
L1及びL3が単結合であり、
L2が前記式(ii)で表される基である、請求項2又は3に記載の化合物。 - Arが、前記式(b-1)、(b-2)、(c-1)、又は(g-1)で表される基であり、
L1が単結合であり、
L2及びL3が前記式(ii)で表される基である、請求項2又は3に記載の化合物。 - Arが、前記式(d-2)、(e-1)、(l-1)、(l-2)、(m-1)、又は(m-2)で表される基であり、
L1及びL2が前記式(ii)で表される基であり、
L3が単結合で表される基である、請求項2又は3に記載の化合物。 - Arが、前記式(b-1)又は(c-1)で表される基であり、
L1及びL2が前記式(ii)で表される基であり、
L3が単結合で表される基である、請求項4又は5に記載の化合物。 - 前記式(ii)で表される基が、p-フェニレン基である、請求項12~17のいずれか1項に記載の化合物。
- R4及びR5が表す置換若しくは無置換の環形成炭素数6~18のアリール基において、該アリール基が、フェニル基又はビフェニリル基である、請求項1~18のいずれか1項に記載の化合物。
- 請求項1~19のいずれか1項に記載の化合物を含む有機エレクトロルミネッセンス素子用材料。
- 陰極、陽極、及び該陰極と該陽極の間に配置された有機薄膜層を有する有機エレクトロルミネッセンス素子であって、該有機薄膜層が1又は複数の層を含み、該有機薄膜層が発光層を含み、該有機薄膜層の少なくとも1層が請求項1~19のいずれか1項に記載の化合物を含む有機エレクトロルミネッセンス素子。
- 陽極と発光層との間に正孔輸送層を含み、該正孔輸送層が前記化合物を含む請求項21に記載の有機エレクトロルミネッセンス素子。
- 陽極と発光層との間に電子阻止層を含み、該電子阻止層が前記化合物を含む請求項21に記載の有機エレクトロルミネッセンス素子。
- 陽極と発光層との間に励起子阻止層を含み、該励起子阻止層が前記化合物を含む請求項21に記載の有機エレクトロルミネッセンス素子。
- 陽極と発光層との間に2以上の層を含む陽極側有機薄膜層を含み、該陽極側有機薄膜層の少なくとも1層が前記化合物を含む請求項21に記載の有機エレクトロルミネッセンス素子。
- 前記陽極側有機薄膜層の2以上の層が正孔輸送層であり、発光層に最も近接する正孔輸送層が前記化合物を含む請求項25に記載の有機エレクトロルミネッセンス素子。
- 請求項21~26のいずれか1項に記載の有機エレクトロルミネッセンス素子を備える電子機器。
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CN107849001B (zh) | 2022-05-10 |
CN107849001A (zh) | 2018-03-27 |
JP6879559B2 (ja) | 2021-06-02 |
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