WO2015072520A1 - 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および電子機器 - 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および電子機器 Download PDFInfo
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- WO2015072520A1 WO2015072520A1 PCT/JP2014/080086 JP2014080086W WO2015072520A1 WO 2015072520 A1 WO2015072520 A1 WO 2015072520A1 JP 2014080086 W JP2014080086 W JP 2014080086W WO 2015072520 A1 WO2015072520 A1 WO 2015072520A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 165
- 239000000463 material Substances 0.000 title claims description 65
- 125000004432 carbon atom Chemical group C* 0.000 claims description 300
- 239000010410 layer Substances 0.000 claims description 279
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 80
- 125000000623 heterocyclic group Chemical group 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 239000002019 doping agent Substances 0.000 claims description 48
- 125000001424 substituent group Chemical group 0.000 claims description 46
- 125000006413 ring segment Chemical group 0.000 claims description 38
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 125000005647 linker group Chemical group 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 125000004104 aryloxy group Chemical group 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 125000002524 organometallic group Chemical group 0.000 claims description 26
- 239000012044 organic layer Substances 0.000 claims description 23
- 125000005110 aryl thio group Chemical group 0.000 claims description 22
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000005104 aryl silyl group Chemical group 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims description 13
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 13
- 125000001769 aryl amino group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 238000005401 electroluminescence Methods 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 7
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 7
- 150000001340 alkali metals Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 150000002910 rare earth metals Chemical class 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 5
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 5
- 150000001341 alkaline earth metal compounds Chemical class 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 150000002926 oxygen Chemical class 0.000 claims description 4
- 150000003248 quinolines Chemical group 0.000 claims description 4
- 150000003463 sulfur Chemical class 0.000 claims description 4
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000004419 alkynylene group Chemical group 0.000 claims description 3
- 150000002909 rare earth metal compounds Chemical class 0.000 claims description 3
- 150000002537 isoquinolines Chemical group 0.000 claims 2
- -1 R 9 Chemical compound 0.000 description 101
- 238000002347 injection Methods 0.000 description 44
- 239000007924 injection Substances 0.000 description 44
- 230000005525 hole transport Effects 0.000 description 42
- 125000003118 aryl group Chemical group 0.000 description 33
- 239000010408 film Substances 0.000 description 32
- 238000000034 method Methods 0.000 description 27
- 125000004429 atom Chemical group 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 22
- 230000004888 barrier function Effects 0.000 description 21
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 20
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 20
- 150000001721 carbon Chemical group 0.000 description 18
- NMLYGLCBSFKJFI-UHFFFAOYSA-N 4-pyridin-2-ylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC=CC=N1 NMLYGLCBSFKJFI-UHFFFAOYSA-N 0.000 description 16
- 239000000758 substrate Substances 0.000 description 16
- 125000001072 heteroaryl group Chemical group 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 12
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 239000011521 glass Substances 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 9
- 125000001624 naphthyl group Chemical group 0.000 description 9
- 150000001454 anthracenes Chemical class 0.000 description 8
- 125000000732 arylene group Chemical group 0.000 description 8
- 239000010409 thin film Substances 0.000 description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 7
- 150000004982 aromatic amines Chemical class 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Chemical compound [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 description 6
- 125000005107 alkyl diaryl silyl group Chemical group 0.000 description 5
- 229910052788 barium Inorganic materials 0.000 description 5
- 150000004696 coordination complex Chemical class 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 125000005105 dialkylarylsilyl group Chemical group 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 238000004949 mass spectrometry Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 230000027756 respiratory electron transport chain Effects 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 125000005106 triarylsilyl group Chemical group 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- 229910052792 caesium Inorganic materials 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 230000005281 excited state Effects 0.000 description 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- 150000002484 inorganic compounds Chemical class 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- 239000012212 insulator Substances 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229960003540 oxyquinoline Drugs 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 125000001725 pyrenyl group Chemical group 0.000 description 4
- 230000006798 recombination Effects 0.000 description 4
- 238000005215 recombination Methods 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 3
- WYECURVXVYPVAT-UHFFFAOYSA-N 1-(4-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Br)C=C1 WYECURVXVYPVAT-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910001508 alkali metal halide Inorganic materials 0.000 description 3
- 150000008045 alkali metal halides Chemical class 0.000 description 3
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000001555 benzenes Chemical group 0.000 description 3
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 3
- 239000000292 calcium oxide Substances 0.000 description 3
- 150000004697 chelate complex Chemical class 0.000 description 3
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000004866 oxadiazoles Chemical class 0.000 description 3
- 125000005561 phenanthryl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 229910052701 rubidium Inorganic materials 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 229910052712 strontium Inorganic materials 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000005388 borosilicate glass Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 150000001717 carbocyclic compounds Chemical class 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 229910052732 germanium Inorganic materials 0.000 description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000005549 heteroarylene group Chemical group 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 150000002503 iridium Chemical class 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000001989 lithium alloy Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000005581 pyrene group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 150000003230 pyrimidines Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
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- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
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- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
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- 238000012546 transfer Methods 0.000 description 1
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- LKNRQYTYDPPUOX-UHFFFAOYSA-K trifluoroterbium Chemical compound F[Tb](F)F LKNRQYTYDPPUOX-UHFFFAOYSA-K 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 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
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- XASAPYQVQBKMIN-UHFFFAOYSA-K ytterbium(iii) fluoride Chemical compound F[Yb](F)F XASAPYQVQBKMIN-UHFFFAOYSA-K 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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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.
- organic electroluminescence devices using organic substances are promising for use as solid light-emitting, inexpensive, large-area full-color display devices, and many developments have been made. ing.
- an organic EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the light emitting layer. When an electric field is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side. Further, the electrons recombine with holes in the light emitting layer to generate an excited state, and energy is emitted as light when the excited state returns to the ground state.
- organic EL elements have a higher driving voltage and lower luminance and luminous efficiency than inorganic light emitting diodes. Recent organic EL elements are gradually improved, but further lower voltage and higher light emission efficiency are required.
- Patent Document 1 describes an organic EL device using a compound having a pyrimidine ring as an electron transport material.
- Patent Document 2 describes that a compound having a pyridine ring and a pyrimidine ring or a triazine ring is used as an electron transport material or a host material of a light emitting layer.
- Patent Document 3 describes a phosphorescent organic EL device using a compound having a plurality of pyridine rings as an electron transport material.
- Patent Document 4 describes an organic EL device using a compound having a biscarbazole skeleton and a nitrogen-containing heterocycle such as a pyridine ring as a host material of a light emitting layer. In each of Patent Documents 1 to 4, attempts are made to reduce the voltage and increase the light emission efficiency of the organic EL device by using a compound having a nitrogen-containing heterocyclic group in the light emitting layer or the electron transporting layer.
- the objective of this invention is the compound which can improve the performance of an organic EL element, the organic electroluminescent element material containing the said compound, the organic electroluminescent element containing the said compound, and the electronic device provided with the said organic electroluminescent element Is to provide.
- the compound according to one embodiment of the present invention is represented by the following general formula (1).
- Each R 3 is independently Hydrogen atom, A halogen atom, Hydroxyl group, A cyano group, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, A substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms, A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, A substituted or unsubstituted arylthio group having 1 to 30 carbon atom
- R 2 is A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
- the substituent is A halogen atom, Hydroxyl group, A cyano group, Nitro group, A carboxy group, A substituted or unsubstituted alkyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkynyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, A substituted or unsubstituted aryl
- L 1 is a single bond or a linking group, and the linking group in L 1 is: Alkenylene group, An alkynylene group, A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A multiple linking group in which 2 to 4 groups selected from the aromatic hydrocarbon groups are bonded; A multiple linking group in which 2 to 4 groups selected from the heterocyclic group are bonded, or a group in which 2 to 4 groups selected from the aromatic hydrocarbon group and the heterocyclic group are bonded It is a multiple linking group.
- the aromatic hydrocarbon group and the heterocyclic group constituting the multiple linking group may be the same or different from each other, and may form a ring when adjacent groups are bonded to each other or may not form a ring.
- L 2 is a linking group, and the linking group has the same meaning as the linking group in L 1 .
- n and m are each independently an integer of 1 or more and 5 or less. When n is an integer of 2 or more and 5 or less, the plurality of Cz are the same as or different from each other. When m is an integer of 2 or more and 5 or less, the plurality of Az are the same as or different from each other.
- Cz is represented by the following general formula (1a), Az is represented by the following general formula (11). )
- X 1 to X 8 are each independently CR or a nitrogen atom.
- R and R 1 are each independently Hydrogen atom, A halogen atom, Hydroxyl group, A cyano group, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, A substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms, A substituted or unsubstituted alkylthio group having 1 to 30
- X 9 is CR 9 or a nitrogen atom
- X 10 is CR 10 or a nitrogen atom
- R 4 to R 6 , R 9 and R 10 are each independently Hydrogen atom, A halogen atom, Hydroxyl group, A cyano group, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, A substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms, A substituted or unsubstit
- R 4 to R 6 , R 9, and R 10 are bonded to form a ring, and another ring is not formed.
- any one of R 4 to R 6 , R 9 and R 10 is a single bond bonded to L 2 .
- the compound which can improve the performance of an organic electroluminescent element, the organic electroluminescent element material containing the said compound, the organic electroluminescent element containing the said compound, and the electron provided with the said organic electroluminescent element Equipment can be provided.
- each R 3 is independently Hydrogen atom, A halogen atom, Hydroxyl group, A cyano group, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, A substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms, A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, A substituted or unsubstituted arylthio group having 1 to 30 carbon atom
- R 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
- the substituent is A halogen atom, Hydroxyl group, A cyano group, Nitro group, A carboxy group, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, A substituted or unsubstituted ary
- L 1 is a single bond or a linking group, and the linking group in L 1 is: Alkenylene group, An alkynylene group, A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A multiple linking group in which 2 to 4 groups selected from the aromatic hydrocarbon groups are bonded; A multiple linking group in which 2 to 4 groups selected from the heterocyclic group are bonded, or a group in which 2 to 4 groups selected from the aromatic hydrocarbon group and the heterocyclic group are bonded It is a multiple linking group.
- the aromatic hydrocarbon group and the heterocyclic group constituting the multiple linking group may be the same or different from each other, and may form a ring when adjacent groups are bonded to each other or may not form a ring.
- L 2 is a linking group, and the linking group has the same meaning as the linking group in L 1 .
- n and m are each independently an integer of 1 or more and 5 or less. When n is an integer of 2 or more and 5 or less, the plurality of Cz are the same as or different from each other. When m is an integer of 2 or more and 5 or less, the plurality of Az are the same as or different from each other.
- Cz is represented by the following general formula (1a), Az is represented by the following general formula (11). )
- X 1 to X 8 are each independently CR or a nitrogen atom.
- R and R 1 are each independently Hydrogen atom, A halogen atom, Hydroxyl group, A cyano group, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, A substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms, A substituted or unsubstituted alkylthio group having 1 to 30
- X 9 is CR 9 or a nitrogen atom
- X 10 is CR 10 or a nitrogen atom
- R 4 to R 6 , R 9 and R 10 are each independently Hydrogen atom, A halogen atom, Hydroxyl group, A cyano group, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, A substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms, A substituted or unsubstit
- R 4 to R 6 , R 9, and R 10 are bonded to form a ring, and another ring is not formed.
- any one of R 4 to R 6 , R 9 and R 10 is a single bond bonded to L 2 .
- the general formula (1) is preferably represented by the following general formula (1A) or (1B).
- L 1 , L 2 , R 2 , R 3 , Az, n, m are respectively L 1 , L 2 , R 2 , R 3 , Az, n, is synonymous with m .
- X 1 ⁇ X 8 are each synonymous with X 1 ⁇ X 8 in the general formula (1a).
- L 1 , L 2 , R 2 , R 3 , Az, n, m are L 1 , L 2 , R 2 , R 3 , Az, n, .R 1, X 1 ⁇ X 8 is synonymous with m are respectively synonymous with R 1, X 1 ⁇ X 8 in the general formula (1a).
- any one of X 1 to X 8 is a carbon atom bonded to L 1 .
- R 4 to R 6 , R 9 and R 10 in the general formula (11) are combined to form a ring.
- any of R 4 to R 6 , R 9 and R 10 that do not form a ring may be a single bond that binds to L 2 .
- any one of R 4 to R 6 , R 9 and R 10 forming a ring is a single bond further bonded to L 2, that is, among R 4 to R 6 , R 9 and R 10 ring formed by either, may be coupled to L 2.
- R 4 and R 9 when R 4 and R 9 form a ring, when R 5 or R 6 that does not form a ring is a single bond bonded to L 2 , As represented by Formula (11A), the ring formed by R 4 and R 9 may have a bond bonded to L 2 .
- R 5, R 6, X 10 have the same meaning as R 5, R 6, X 10 in the general formula (11).
- X 1 to X 8 are each independently CR.
- Az is a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrimidine ring, a substituted or unsubstituted It is preferably selected from any of a triazine ring, a substituted or unsubstituted quinoline ring, a substituted or unsubstituted isoquinoline ring, a substituted or unsubstituted quinazoline ring, and a substituted or unsubstituted phenanthroline ring.
- Az is any one of an unsubstituted pyridine ring, an unsubstituted pyrimidine ring, an unsubstituted triazine ring, an unsubstituted quinoline ring, an unsubstituted isoquinoline ring, an unsubstituted quinazoline ring, and an unsubstituted phenanthroline ring.
- Az is preferably a group represented by any of the following general formulas (11-a) to (11-x), and among these, a monocyclic structure having no condensed ring is preferable. And a group represented by any one of (11-a) to (11-g) is more preferable.
- the group represented by any one of the following formulas (11-a) to (11-x) may further have a substituent. In the case of “substituted”, it has a substituent.
- the bond is a bond bonded to L 2 in the general formula (1), (1A) or (1B).
- X 9 is preferably CR 9 and X 10 is preferably CR 10 . That is, in the general formulas (1), (1A) and (B), it is preferable that the Az is a substituted or unsubstituted pyridine ring.
- the Az is more preferably an unsubstituted pyridine ring, and is preferably represented by any one of the general formulas (11-a) to (11-c).
- the n is preferably 1 or 2
- the m is preferably 1.
- the general formula (1A) is preferably represented by the following general formula (12A-1) or (12A-2), and the general formula (1B) is represented by the following general formula (12B-1) or (12B- It is preferable to be represented by 2).
- L 1 , L 2, R 2, R 3, Az is the L 1, L 2, R 2 , R 3, Az synonymous in the general formula (1) there .
- R 11, R 12 are, .R 11, R 12 bonded to any carbon atom of the carbazolyl group, R 3 as synonymous .p and q in the general formula (1) is 4.
- the plurality of R 11 and R 12 are the same or different.
- L 1 , L 2, R 2, R 3, Az is in L 1, L 2, R 2 , R 3, Az as defined in the general formula (1)
- R 11 , R 12 , R 13 , and R 14 are bonded to any carbon atom of the carbazolyl group, and R 11 , R 12 , R 13 , and R 14 are R 3 and R 3 in the general formula (1), respectively.
- P, q, r, and s are 4.
- the plurality of R 11 , R 12 , R 13 , and R 14 are the same or different.
- L 1 , L 2, R 2, R 3, Az is the L 1, L 2, R 2 , R 3, Az synonymous in the general formula (1)
- R 1 has the same meaning as R 3 in the general formula (1)
- R 11 and R 12 are any carbon of the carbazolyl group.
- .R 11, R 12 that binds to atom, R 3 as synonymous .p of the general formula (1) is 4, q is 3. more R 11, R 12 are each the same Or different.
- L 1 , L 2, R 2, R 3, Az is the L 1, L 2, R 2 , R 3, Az synonymous in the general formula (1)
- R 1 and R 15 are each independently synonymous with R 3 in the general formula (1)
- R 11 , R 12 , R 13 and R 14 are bonded to any carbon atom of the carbazolyl group
- R 11 , R 12 , R 13 and R 14 have the same meaning as R 3 in the general formula (1)
- p and r are 4 and q and s are 3.
- the plurality of R 11 , R 12 , R 13 , and R 14 are the same or different.
- the compound represented by the general formula (1) is preferably represented by the general formula (1A), and the general formulas (11A), (12A-1) and (12A-2) It is more preferable that it is represented by any of the above.
- L 1 is preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and is represented by any of the following formulas (L-1a) to (L-1f) It is more preferable. Note that the group represented by any one of the following formulas (L-1a) to (L-1f) may further have a substituent. In the case of “substituted”, it has a substituent.
- L 1 is preferably a substituted or unsubstituted benzene ring, and more preferably represented by the above formula (L-1a).
- the general formula (1) is preferably represented by the following general formula (13A).
- L 2, R 2, R 3, Az is .R 11, R 12 the same meanings as L 2, R 2, R 3 , Az in the general formula (1), R 13 and R 14 are bonded to any carbon atom of the carbazolyl group, and R 11 , R 12 , R 13 , R 14 , R 16 , R 17 , and R 18 are R 3 in the general formula (1), respectively.
- P, q, r, and s are 4.
- the plurality of R 11 , R 12 , R 13 , and R 14 are the same or different.
- the general formula (1A) is preferably represented by the following general formula (15A).
- R 2, L 2, Az is .R 11
- R 12 is synonymous with R 2
- Az in the general formula (1) are respectively the general formula (It is synonymous with R 3 in (1).
- the plurality of R 11 are the same or different from each other.
- the plurality of R 12 are the same or different from each other. P and q are 4.
- L 2 is preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
- L 2 is a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, it is preferably a dibenzofuran ring or a dibenzothiophene ring.
- L 2 is more preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and as the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, A substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted biphenylene ring is preferred.
- L 2 is more preferably a group represented by any of the following formulas (L-2a) to (L-2f). Note that the group represented by any one of the following formulas (L-2a) to (L-2f) may further have a substituent. In the case of “substituted”, it has a substituent.
- L 2 is preferably a substituted or unsubstituted benzene ring.
- the L 2 is more preferably represented by any of the above formulas (L-2a) to (L-2c), and more preferably represented by the above formula (L-2a).
- R 2 is preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and is represented by any of the following formulas (R-2a) to (R-2e) It is preferable. Note that the group represented by any one of the following formulas (R-2a) to (R-2e) may further have a substituent. In the case of “substituted”, it has a substituent.
- R 2 is preferably a substituted or unsubstituted phenyl group, and more preferably represented by the above formula (R-2a).
- the general formula (15A) is more preferably represented by the following general formula (16A).
- Az is synonymous with Az in the general formula (1).
- R 11 and R 12 are synonymous with R 3 in the general formula (1).
- Plural R 11 Are the same or different from each other, and the plurality of R 12 are the same or different from each other. P and q are 4.
- Examples of the aromatic hydrocarbon group having 6 to 30 ring carbon atoms (sometimes referred to as an aryl group) in the present embodiment include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, and a phenanthryl group.
- the aromatic hydrocarbon group in this embodiment preferably has 6 to 20 ring carbon atoms, and more preferably 6 to 12 carbon atoms.
- aromatic hydrocarbon groups a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a terphenyl group, and a fluorenyl group are more preferable.
- the aromatic hydrocarbon group having 6 to 24 ring carbon atoms in the first ring structure of the present embodiment a group having 6 to 24 ring carbon atoms among the aromatic hydrocarbon groups described above is used. be able to.
- a heterocyclic group having 5 to 30 ring atoms (sometimes referred to as a heteroaryl group, a heteroaromatic ring group, or an aromatic heterocyclic group) has nitrogen, sulfur, oxygen as a heteroatom.
- it contains at least one atom selected from the group consisting of silicon, selenium atom, and germanium atom, and more preferably contains at least one atom selected from the group consisting of nitrogen, sulfur, and oxygen preferable.
- heterocyclic group having 5 to 30 ring atoms in the present embodiment examples include a pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolyl group, isoquinolinyl group, naphthyridinyl group, phthalazinyl group, quinoxalinyl group, Quinazolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indolyl group, benzimidazolyl group, indazolyl group, imidazolpyridinyl group, benz Triazolyl, carbazolyl, furyl, thienyl, oxazolyl, thiazolyl, isoxazolyl, isothiazo
- the number of ring-forming atoms of the heterocyclic group is preferably 5 to 20, and more preferably 5 to 14.
- the substituted or unsubstituted aromatic hydrocarbon having 6 to 30 ring carbon atoms in the present embodiment is attached to the 9th-position nitrogen atom.
- the group or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms is preferably substituted.
- a group having 6 to 24 ring atoms among the above heterocyclic groups can be used.
- the heterocyclic group may be a group derived from a partial structure represented by the following general formulas (XY-1) to (XY-18), for example.
- X and Y are each independently a hetero atom, preferably an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, or a germanium atom.
- the partial structures represented by the general formulas (XY-1) to (XY-18) have a bond at an arbitrary position to be a heterocyclic group, and this heterocyclic group has a substituent. Also good.
- the substituted or unsubstituted carbazolyl group may also include, for example, a group in which a ring is further condensed with respect to a carbazole ring represented by the following formula. Such a group may also have a substituent. Also, the position of the joint can be changed as appropriate.
- the alkyl group having 1 to 30 carbon atoms may be linear, branched or cyclic.
- the linear or branched alkyl group include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl
- the linear or branched alkyl group preferably has 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms.
- An amyl group, an isoamyl group, and a neopentyl group are more preferable.
- Examples of the cycloalkyl group in this embodiment include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, an adamantyl group, and a norbornyl group.
- the number of carbon atoms forming the ring of the cycloalkyl group is preferably 3 to 10, and more preferably 5 to 8.
- a cyclopentyl group and a cyclohexyl group are more preferable.
- halogenated alkyl group in which the alkyl group is substituted with a halogen atom examples include groups in which the alkyl group having 1 to 30 carbon atoms is substituted with one or more halogen groups. Specific examples include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a trifluoromethylmethyl group, a trifluoroethyl group, and a pentafluoroethyl group.
- the alkenyl group having 2 to 30 carbon atoms may be linear, branched, or cyclic, and examples thereof include a vinyl group, a propenyl group, a butenyl group, an oleyl group, and an eicosapentaenyl group.
- a vinyl group a propenyl group, a butenyl group, an oleyl group, and an eicosapentaenyl group.
- the alkynyl group having 2 to 30 carbon atoms may be linear, branched or cyclic, and examples thereof include ethynyl, propynyl, 2-phenylethynyl and the like.
- alkylsilyl group having 3 to 30 carbon atoms in the present embodiment examples include a trialkylsilyl group having an alkyl group exemplified as the alkyl group having 1 to 30 carbon atoms, specifically, a trimethylsilyl group and a triethylsilyl group.
- the three alkyl groups in the trialkylsilyl group may be the same or different.
- Examples of the arylsilyl group having 6 to 60 ring carbon atoms in the present embodiment include a dialkylarylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group.
- the dialkylarylsilyl group has, for example, two alkyl groups exemplified as the above alkyl group having 1 to 30 carbon atoms, and one dialkylarylsilyl group having one aromatic hydrocarbon group having 6 to 30 ring carbon atoms. Is mentioned.
- the carbon number of the dialkylarylsilyl group is preferably 8-30.
- the alkyldiarylsilyl group includes, for example, one alkyl group exemplified as the alkyl group having 1 to 30 carbon atoms, and two alkyl diarylsilyl groups having the two aromatic hydrocarbon groups having 6 to 30 ring carbon atoms. Is mentioned.
- the alkyldiarylsilyl group preferably has 13 to 30 carbon atoms.
- Examples of the triarylsilyl group include a triarylsilyl group having three aromatic hydrocarbon groups having 6 to 30 ring carbon atoms.
- the carbon number of the triarylsilyl group is preferably 18-30.
- the alkoxy group having 1 to 30 carbon atoms in this embodiment is represented by —OZ 1 .
- Z 1 include the above alkyl groups having 1 to 30 carbon atoms.
- Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group.
- Examples of the halogenated alkoxy group in which the alkoxy group is substituted with a halogen atom include groups in which the alkoxy group having 1 to 30 carbon atoms is substituted with one or more halogen groups.
- the aryloxy group having 6 to 30 ring carbon atoms in the present embodiment is represented by —OZ 2 .
- Z 2 include the aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or the monocyclic group and condensed ring group described later.
- Examples of the aryloxy group include a phenoxy group.
- the alkylamino group having 2 to 30 carbon atoms in the present embodiment is represented by —NHR V or —N (R V ) 2 .
- RV include the alkyl group having 1 to 30 carbon atoms.
- the arylamino group having 6 to 60 ring carbon atoms in the present embodiment is represented by —NHR W or —N (R W ) 2 .
- R W and an aromatic hydrocarbon group of the ring carbon atoms 6 to 30.
- the alkylthio group having 1 to 30 carbon atoms in this embodiment is represented by —SR V.
- RV include the alkyl group having 1 to 30 carbon atoms.
- An arylthio group having 6 to 30 ring carbon atoms is represented by —SR W.
- R W and an aromatic hydrocarbon group of the ring carbon atoms 6 to 30.
- halogen atom in this embodiment examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferable.
- a multiple linking group formed by bonding 2 to 4 groups selected from aromatic hydrocarbon groups and a multiple linking group formed by bonding 2 to 4 groups selected from heterocyclic groups.
- a multiple linking group formed by bonding two to four groups selected from an aromatic hydrocarbon group and the heterocyclic group is selected from the aromatic hydrocarbon group and the heterocyclic group;
- Examples of the multiple linking group formed by bonding 2 to 4 groups selected from the aromatic hydrocarbon group and the heterocyclic group include heterocyclic group-aromatic hydrocarbon group, aromatic hydrocarbon group-heterocyclic group , Aromatic hydrocarbon group-heterocyclic group-aromatic hydrocarbon group, heterocyclic group-aromatic hydrocarbon group-heterocyclic group, aromatic hydrocarbon group-heterocyclic group-aromatic hydrocarbon group-heterocyclic group And heterocyclic group-aromatic hydrocarbon group-heterocyclic group-aromatic hydrocarbon group and the like.
- a divalent group formed by bonding the aromatic hydrocarbon group and the heterocyclic group one by one that is, a heterocyclic group-aromatic hydrocarbon group, and an aromatic hydrocarbon group-heterocyclic group.
- Specific examples of the aromatic hydrocarbon group and the heterocyclic group in these multiple linking groups include the groups described for the aromatic hydrocarbon group and the heterocyclic group.
- the number of ring-forming carbon atoms constitutes 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). Represents the number of carbon atoms in the atom.
- the carbon contained in the substituent is not included in the number of ring-forming carbons.
- the “ring-forming carbon number” described below is the same unless otherwise specified.
- the benzene ring has 6 ring carbon atoms
- the naphthalene ring has 10 ring carbon atoms
- the pyridinyl group has 5 ring carbon atoms
- the furanyl group has 4 ring carbon atoms.
- the carbon number of the alkyl group is not included in the number of ring-forming carbons.
- the carbon number of the fluorene ring as a substituent is not included in the number of ring-forming carbons.
- the number of ring-forming atoms means a compound (for example, a monocyclic compound, a condensed ring compound, a bridging compound, a carbocyclic compound, a heterocycle) having a structure in which atoms are bonded in a cyclic manner (for example, a single ring, a condensed ring, or a ring assembly).
- the ring 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.
- a hydrogen atom bonded to a carbon atom of a pyridine ring or a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms. Further, when, for example, a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the number of atoms of the fluorene ring as a substituent is not included in the number of ring-forming atoms.
- the hydrogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (Protium), deuterium (Deuterium), and tritium (Tritium).
- the substituent in the case of “substituted or unsubstituted” includes the aromatic hydrocarbon group, heterocyclic group, alkyl group (straight chain or branched chain alkyl group, cycloalkyl group) as described above.
- an alkenyl group and an alkynyl group are also included.
- an aromatic hydrocarbon group, a heterocyclic group, an alkyl group, a halogen atom, an alkylsilyl group, an arylsilyl group, and a cyano group are preferable, and more preferable in the description of each substituent.
- the specific substituents are preferred.
- “unsubstituted” in the case of “substituted or unsubstituted” means that a hydrogen atom is bonded without being substituted with the substituent.
- carbon number XX to YY in the expression “substituted or unsubstituted ZZ group having XX to YY” represents the number of carbon atoms in the case where the ZZ group is unsubstituted and substituted. In this case, the number of carbon atoms in the substituent is not included.
- YY is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
- 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 and substituted.
- R 2 has a substituent, that is, a substituted XX group
- the substituent is a halogen atom, a hydroxyl group, a cyano group, a nitro group, a carboxy group, a substituted or unsubstituted carbon number of 1 to 30 Alkyl group, substituted or unsubstituted alkenyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkynyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, substituted or unsubstituted An arylsilyl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubsti
- the compound of this embodiment can be used as an organic EL device material.
- the compound of this embodiment may be used alone as a material for an organic EL device, or the compound of this embodiment may be used together with other materials as a material for an organic EL device.
- the organic EL element in one embodiment of the present invention has a cathode, an anode, and an organic layer disposed between the cathode and the anode.
- the organic layer is composed of a plurality of layers including at least a light emitting layer.
- the organic layer includes at least a light emitting layer and includes an electron transport zone.
- the electron transport zone is a layer provided between the light-emitting layer and the cathode, and the electron transport zone includes at least an electron injection layer, and may include an electron injection layer and an electron transport layer.
- a hole barrier layer or a space layer may be included.
- a layer employed in a known organic EL device such as a hole injection layer, a hole transport layer, or an electron barrier layer may be further included.
- the organic layer may contain an inorganic compound.
- the organic EL element may be a fluorescent or phosphorescent monochromatic light emitting element, a fluorescent and phosphorescent hybrid white light emitting element, or a simple type having a single light emitting unit.
- the tandem type having the light emitting unit may be used, and among them, the phosphorescent type is preferable.
- the following element structure can be mentioned as a typical element structure of a simple type organic EL element.
- Anode / light emitting unit / cathode The above light emitting unit may be a laminated type having a plurality of phosphorescent light emitting layers and fluorescent light emitting layers. In that case, the light emitting unit is generated by a phosphorescent light emitting layer between the light emitting layers. In order to prevent the excitons from diffusing into the fluorescent light emitting layer, a space layer may be provided. A typical layer structure of the light emitting unit is shown below.
- A Hole transport layer / light emitting layer (/ electron transport layer)
- B Hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer (/ electron transport layer)
- C Hole transport layer / phosphorescent layer / space layer / fluorescent layer (/ electron transport layer)
- D Hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer / space layer / fluorescent light emitting layer (/ electron transport layer)
- E Hole transport layer / first phosphorescent light emitting layer / space layer / second phosphorescent light emitting layer / space layer / fluorescent light emitting layer (/ electron transport layer)
- F Hole transport layer / phosphorescent layer / space layer / first fluorescent layer / second fluorescent layer (/ electron transport layer)
- G Hole transport layer / electron barrier layer / light emitting layer (/ electron transport layer)
- H Hole transport layer / light emitting layer / hole barrier layer (
- the phosphorescent light-emitting layer or the fluorescent light-emitting layer in each of the light-emitting units can be configured to exhibit different emission colors.
- hole transport layer / first phosphorescent light emitting layer (red light emitting) / second phosphorescent light emitting layer (green light emitting) / space layer / fluorescent light emitting layer (blue light emitting) / electrons examples thereof include a layer configuration such as a transport layer.
- An electron barrier layer may be provided as appropriate between each light emitting layer and the hole transport layer or between each light emitting layer and the 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, a light-emitting unit similar to the above-described light-emitting unit is used. You can choose.
- 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 electrons are supplied to the first light emitting unit and holes are supplied to the second light emitting unit.
- a host combined with a fluorescent dopant is referred to as a fluorescent host
- a host combined with a phosphorescent dopant is referred to as a phosphorescent host.
- Fluorescent and phosphorescent hosts are not distinguished only by molecular structure. That is, the phosphorescent host means a material constituting a phosphorescent light emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material constituting a fluorescent light emitting layer. The same applies to the fluorescent host.
- FIG. 1 schematic structure of an example of the organic EL element in this embodiment is shown.
- An organic EL element 1 shown in FIG. 1 includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4.
- the organic layer 10 is formed by laminating a hole injection / transport layer 6, a light emitting layer 5, an electron transport layer 7, and an electron injection layer 8 in order from the anode 3 side.
- the electron transport layer 7 and the electron injection layer 8 constitute an electron transport zone 11.
- the electron transport zone 11 preferably includes the compound according to the embodiment of the present invention described above.
- the electron transport zone 11 includes an electron transport layer 7 and an electron injection layer 8.
- the compound according to an embodiment of the present invention may be included in any layer of the electron transport zone 11, but is included in the electron injection layer 8 in the present embodiment.
- band 11 in this embodiment contains the electron donating dopant mentioned later, it is preferable.
- the electron injection layer has a function of efficiently injecting electrons from the cathode into the organic layer unit.
- an organic layer close to the cathode is used as an electron injection layer.
- the electron injection layer 8 of this embodiment includes the compound according to one embodiment of the present invention described above. That is, the general formulas (1), (1A), (1B), (13A), (15A) to (16A), (12A-1) to (12A-2), and (12B-1) to (12B) -2) is included.
- the compound of the present embodiment represented by any one of (2) has a nitrogen-containing heterocyclic group represented by Az at the molecular end, and thus has a high electron injection property.
- the electron transport layer 7 is an organic layer formed between the light emitting layer and the cathode, and has a function of transporting electrons from the cathode to the light emitting layer.
- the compound and organic EL device material according to the above-described embodiment of the present invention are also suitable as an electron transport layer material for forming an electron transport layer.
- an aromatic heterocyclic compound containing one or more heteroatoms in the molecule is preferably used, and a nitrogen-containing ring derivative is more preferable.
- the nitrogen-containing ring derivative is preferably an aromatic ring having a nitrogen-containing 6-membered ring or 5-membered ring skeleton, or a condensed aromatic ring compound having a nitrogen-containing 6-membered ring or 5-membered ring skeleton.
- a nitrogen-containing ring metal chelate complex represented by the following formula (A) is preferable.
- R 2 to R 7 in the formula (A) which is a nitrogen-containing ring metal chelate complex are each independently a hydrogen atom, a halogen atom, a hydroxyl group, an amino group, a hydrocarbon group having 1 to 40 carbon atoms, or 1 to A 40 alkoxy group, an aryloxy group having 6 to 50 carbon atoms, an alkoxycarbonyl group, or an aromatic heterocyclic group having 5 to 50 ring carbon atoms, which may be substituted.
- Examples of the halogen atom include fluorine, chlorine, bromine, iodine and the like.
- the amino group which may be substituted include an alkylamino group, an arylamino group and an aralkylamino group.
- the alkylamino group and the aralkylamino group are represented as —NQ 1 Q 2 .
- Q 1 and Q 2 each independently represents an alkyl group having 1 to 20 carbon atoms or an aralkyl group having 1 to 20 carbon atoms.
- One of Q 1 and Q 2 may be a hydrogen atom.
- the arylamino group is represented as —NAr 1 Ar 2, and Ar 1 and Ar 2 each independently represent a non-condensed aromatic hydrocarbon group or a condensed aromatic hydrocarbon group having 6 to 50 carbon atoms.
- Ar 1 and Ar 2 may be a hydrogen atom.
- the hydrocarbon group having 1 to 40 carbon atoms includes an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, and an aralkyl group.
- the alkoxycarbonyl group is represented as —COOY ′, and Y ′ represents an alkyl group having 1 to 20 carbon atoms.
- M is aluminum (Al), gallium (Ga) or indium (In), and is preferably In.
- L is a group represented by the following formula (A ′) or (A ′′).
- R 8 to R 12 are each independently a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other form a cyclic structure. May be.
- R 13 to R 27 are each independently a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other have a cyclic structure. It may be formed.
- the hydrocarbon group having 1 to 40 carbon atoms represented by R 8 to R 12 and R 13 to R 27 in the formula (A ′) and the formula (A ′′) is a nitrogen-containing ring metal chelate complex in the formula (A).
- the divalent group in the case where the adjacent groups of R 8 to R 12 and R 13 to R 27 form a cyclic structure is the same as the hydrocarbon group represented by R 2 to R 7 of Examples include a methylene group, a pentamethylene group, a hexamethylene group, a diphenylmethane-2,2′-diyl group, a diphenylethane-3,3′-diyl group, and a diphenylpropane-4,4′-diyl group.
- 8-hydroxyquinoline or a metal complex of its derivative, an oxadiazole derivative, or a nitrogen-containing heterocyclic derivative is preferable.
- a metal chelate oxinoid compound containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline), for example, tris (8-quinolinol) aluminum is used.
- 8-quinolinol or 8-hydroxyquinoline a metal chelate oxinoid compound containing a chelate of oxine
- tris (8-quinolinol) aluminum is used.
- an oxadiazole derivative it illustrates below.
- Ar 17 , Ar 18 , Ar 19 , Ar 21 , Ar 22 and Ar 25 each represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 carbon atoms or a condensed aromatic hydrocarbon group
- Ar 17 and Ar 18 , Ar 19 and Ar 21 , Ar 22 and Ar 25 may be the same as or different from each other.
- the aromatic hydrocarbon group or the condensed aromatic hydrocarbon group include a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a perylenyl group, and a pyrenyl group.
- substituents include alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, and cyano groups.
- Ar 20 , Ar 23 and Ar 24 each represent a substituted or unsubstituted divalent aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 50 carbon atoms, and Ar 23 and Ar 24 are identical to each other. But it can be different.
- the divalent aromatic hydrocarbon group or condensed aromatic hydrocarbon group include a phenylene group, a naphthylene group, a biphenylene group, an anthranylene group, a peryleneylene group, and a pyrenylene group.
- substituents include alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, and cyano groups.
- an electron transporting compound having a good thin film forming property is preferably used. Examples of these electron transfer compounds are given below.
- the nitrogen-containing heterocyclic derivative as the electron transfer compound is a nitrogen-containing heterocyclic derivative composed of an organic compound having the following formula, and includes a nitrogen-containing compound that is not a metal complex.
- the nitrogen-containing heterocyclic derivative as a child-transmitting compound includes a compound having a 5-membered or 6-membered ring containing a skeleton represented by the following formula (B) and a compound having a structure represented by the following formula (C). It is done.
- X represents a carbon atom or a nitrogen atom.
- Z 1 and Z 2 each independently represents an atomic group capable of forming a nitrogen-containing heterocycle.
- the nitrogen-containing heterocyclic derivative is more preferably an organic compound having a nitrogen-containing aromatic polycyclic group consisting of a 5-membered ring or a 6-membered ring. Further, in the case of such a nitrogen-containing aromatic polycyclic group having a plurality of nitrogen atoms, the nitrogen-containing compound having a skeleton in which the above formulas (B) and (C) or the above formula (B) and the following formula (D) are combined. Aromatic polycyclic organic compounds are preferred.
- the nitrogen-containing group of the nitrogen-containing aromatic polycyclic organic compound is selected from, for example, nitrogen-containing heterocyclic groups represented by the following formulae.
- R is an aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 40 carbon atoms, an aromatic heterocyclic group or condensed aromatic heterocyclic group having 3 to 40 carbon atoms, 1 to 20 is an alkyl group or an alkoxy group having 1 to 20 carbon atoms, n is an integer of 0 to 5, and when n is an integer of 2 or more, a plurality of R may be the same or different from each other.
- preferred specific compounds include nitrogen-containing heterocyclic derivatives represented by the following formula (D1). HAr-L 1 -Ar 1 -Ar 2 (D1)
- HAr is a substituted or unsubstituted nitrogen-containing heterocyclic group having 3 to 40 carbon atoms
- L 1 is a single bond, substituted or unsubstituted aromatic hydrocarbon having 6 to 40 carbon atoms.
- Ar 1 is a substituted or unsubstituted 2 to 6 carbon atom having 2 to 6 carbon atoms.
- Ar 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 carbon atoms, a condensed aromatic hydrocarbon group, or a substituted or unsubstituted aromatic group having 3 to 40 carbon atoms. It is a heterocyclic group or a condensed aromatic heterocyclic group.
- HAr is selected from the following group, for example.
- L 1 in the formula (D1) is selected from the following group, for example.
- Ar 1 in the formula (D1) is selected from, for example, arylanthranyl groups of the following formulas (D2) and (D3).
- R 1 to R 14 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or a carbon number.
- R 1 to R 8 may be nitrogen-containing heterocyclic derivatives each of which is a hydrogen atom.
- Ar 2 in the formula (D1) is selected from the following group, for example.
- a compound represented by the following formula (D4) is also preferably used as the nitrogen-containing aromatic polycyclic organic compound as the electron-transfer compound.
- R 1 to R 4 are each independently a hydrogen atom, a substituted or unsubstituted aliphatic group having 1 to 20 carbon atoms, a substituted or unsubstituted aliphatic group having 3 to 20 carbon atoms.
- X 1 and X 2 each independently represents an oxygen atom, Represents a sulfur atom or a dicyanomethylene group.
- a compound represented by the following formula (D5) is also preferably used as the electron transfer compound.
- R 1 , R 2 , R 3 and R 4 are the same or different groups, and are an aromatic hydrocarbon group or a condensed aromatic hydrocarbon group represented by the following formula (D6). It is.
- R 5 , R 6 , R 7 , R 8 and R 9 are the same or different from each other, and are a hydrogen atom, a saturated or unsaturated alkoxy group having 1 to 20 carbon atoms, saturated or An unsaturated alkyl group having 1 to 20 carbon atoms, an amino group, or an alkylamino group having 1 to 20 carbon atoms. At least one of R 5 , R 6 , R 7 , R 8 and R 9 is a group other than a hydrogen atom.
- the electron transfer compound may be a polymer compound containing the nitrogen-containing heterocyclic group or the nitrogen-containing heterocyclic derivative.
- the electron transport layer of the organic EL device of the present invention more preferably contains at least one nitrogen-containing heterocyclic derivative represented by the following formulas (E) to (G).
- Z 1 , Z 2 and Z 3 are each independently a nitrogen atom or a carbon atom.
- R 1 and R 2 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, substituted or unsubstituted carbon An alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
- n is an integer of 0 to 5, and when n is an integer of 2 or more, the plurality of R 1 may be the same or different from each other. Further, two adjacent R 1 may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring.
- Ar 1 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
- Ar 2 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted Alternatively, it is an unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
- Ar 1 or Ar 2 is a substituted or unsubstituted condensed aromatic hydrocarbon ring group having 10 to 50 ring carbon atoms or a substituted or unsubstituted condensed aromatic group having 9 to 50 ring atoms. It is a heterocyclic group.
- Ar 3 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 50 ring atoms.
- L 1 , L 2 and L 3 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent ring having 9 to 50 ring atoms.
- aryl group having 6 to 50 ring carbon atoms examples include phenyl group, naphthyl group, anthryl group, phenanthryl group, naphthacenyl group, chrysenyl group, pyrenyl group, biphenyl group, terphenyl group, tolyl group, fluoranthenyl group, fluorenyl Groups and the like.
- heteroaryl group having 5 to 50 ring atoms examples include pyrrolyl group, furyl group, thienyl group, silolyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuryl group, imidazolyl group, pyrimidyl group, carbazolyl group, selenophenyl group Oxadiazolyl group, triazolyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinoxalinyl group, acridinyl group, imidazo [1,2-a] pyridinyl group, imidazo [1,2-a] pyrimidinyl group and the like.
- Examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group.
- Examples of the haloalkyl group having 1 to 20 carbon atoms include groups obtained by substituting one or more hydrogen atoms of the alkyl group with at least one halogen atom selected from fluorine, chlorine, iodine and bromine.
- Examples of the alkoxy group having 1 to 20 carbon atoms include groups having the above alkyl group as an alkyl moiety.
- Examples of the arylene group having 6 to 50 ring carbon atoms include groups obtained by removing one hydrogen atom from the aryl group.
- Examples of the divalent condensed aromatic heterocyclic group having 9 to 50 ring atoms include groups obtained by removing one hydrogen atom from the condensed aromatic heterocyclic group described as the heteroaryl group.
- the thickness of the electron transport layer is not particularly limited, but is preferably 1 nm to 100 nm.
- the electron transport zone 11 of the organic EL element 1 may include a second electron injection layer in addition to the electron injection layer 8.
- the second electron injection layer may be provided between the electron transport layer and the electron injection layer 8.
- an insulator or a semiconductor As a constituent component of the second electron injection layer, it is preferable to use an insulator or a semiconductor as an inorganic compound in addition to the nitrogen-containing ring derivative. If the second electron injection layer is made of an insulator or a semiconductor, current leakage can be effectively prevented and the electron injection property can be improved.
- an insulator it is preferable to use at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides. If the second electron injection layer is composed of these alkali metal chalcogenides or the like, it is preferable in that the electron injection property can be further improved.
- preferable alkali metal chalcogenides include, for example, Li 2 O, K 2 O, Na 2 S, Na 2 Se, and Na 2 O
- preferable alkaline earth metal chalcogenides include, for example, CaO, BaO. , SrO, BeO, BaS and CaSe.
- preferable alkali metal halides include, for example, LiF, NaF, KF, LiCl, KCl, and NaCl.
- preferable alkaline earth metal halides include fluorides such as CaF 2 , BaF 2 , SrF 2 , MgF 2 and BeF 2 , and halides other than fluorides.
- the inorganic compound constituting the second electron injection layer is preferably a microcrystalline or amorphous insulating thin film. If the second electron injection layer is composed of these insulating thin films, a more uniform thin film is formed, and pixel defects such as dark spots can be reduced. Examples of such inorganic compounds include alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides.
- the preferred thickness of the layer is about 0.1 nm to 15 nm.
- the organic EL device of the present embodiment preferably has at least one of an electron donating dopant and an organometallic complex in the electron transport zone or the interface region between the cathode and the organic layer. According to such a configuration, it is possible to improve the light emission luminance and extend the life of the organic EL element.
- the electron donating dopant include at least one selected from alkali metals, alkali metal compounds, alkaline earth metals, alkaline earth metal compounds, rare earth metals, rare earth metal compounds, and the like.
- the organometallic complex include at least one selected from an organometallic complex containing an alkali metal, an organometallic complex containing an alkaline earth metal, an organometallic complex containing a rare earth metal, and the like.
- alkali metal examples include lithium (Li) (work function: 2.93 eV), sodium (Na) (work function: 2.36 eV), potassium (K) (work function: 2.28 eV), rubidium (Rb) (work Function: 2.16 eV), cesium (Cs) (work function: 1.95 eV), and the like, and an alkali metal having a work function of 2.9 eV or less is preferable.
- K, Rb, and Cs are preferable, Rb or Cs is more preferable, and Cs is more preferable.
- alkaline earth metal examples include calcium (Ca) (work function: 2.9 eV), strontium (Sr) (work function: 2.0 eV to 2.5 eV), barium (Ba) (work function: 2.52 eV).
- An alkaline earth metal having a work function of 2.9 eV or less is preferable.
- the rare earth metal examples include scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb), and the like.
- a rare earth metal having a work function of 2.9 eV or less is preferable.
- preferred metals are particularly high in reducing ability, and by adding a relatively small amount to the electron injection region, it is possible to improve the light emission luminance and extend the life of the organic EL element.
- alkali metal compound examples include lithium oxide (Li 2 O), cesium oxide (Cs 2 O), alkali oxides such as potassium oxide (K 2 O), lithium fluoride (LiF), and sodium fluoride (NaF). And alkali halides such as cesium fluoride (CsF) and potassium fluoride (KF). Lithium fluoride (LiF), lithium oxide (Li 2 O), and sodium fluoride (NaF) are preferable.
- alkaline earth metal compound examples include barium oxide (BaO), strontium oxide (SrO), and calcium oxide (CaO).
- alkaline earth metal compound examples include barium strontate mixed with BaO and SrO (Ba x Sr 1-x O) (0 ⁇ x ⁇ 1), and barium calcium oxide mixed with BaO and CaO ( Ba x Ca 1-x O) (0 ⁇ x ⁇ 1).
- BaO, SrO, and CaO are preferable.
- rare earth metal compounds for example, ytterbium fluoride (YbF 3), scandium fluoride (ScF 3), scandium oxide (ScO 3), yttrium oxide (Y 2 O 3), cerium oxide (Ce 2 O 3), fluoride of gadolinium (GdF 3), such as terbium fluoride (TbF 3) can be mentioned, YbF 3, ScF 3, TbF 3 are preferable.
- the organometallic complex is not particularly limited as long as it contains at least one of an alkali metal ion, an alkaline earth metal ion, and a rare earth metal ion as a metal ion as described above.
- the ligand of the organometallic complex include quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiaryloxadiazole, hydroxydiarylthiadiazole, hydroxyphenylpyridine, hydroxyphenyl Benzimidazole, hydroxybenzotriazole, hydroxyfulborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, ⁇ -diketones, azomethines, and derivatives thereof are preferred, but not limited thereto.
- the addition form of the electron donating dopant and the organometallic complex is preferably formed in a layered or island shape in the interface region.
- a forming method while depositing at least one of an electron donating dopant and an organometallic complex by a resistance heating vapor deposition method, an organic material which is a light-emitting material or an electron injection material for forming an interface region is vapor-deposited at the same time.
- a method of dispersing at least one of a donor dopant and an organometallic complex reducing dopant is preferable.
- At least one of the electron donating dopant and the organometallic complex in a layered form, after forming the light emitting material or the electron injecting material as the organic layer at the interface in a layered form, at least one of the electron donating dopant and the organometallic complex is formed.
- These are vapor-deposited by a resistance heating vapor deposition method alone, preferably with a layer thickness of 0.1 nm to 15 nm.
- the electron donating dopant and the organometallic complex is formed in an island shape
- the electron donating dopant and the organometallic complex At least one of them is vapor-deposited by a resistance heating vapor deposition method, preferably with an island thickness of 0.05 nm to 1 nm.
- the organic EL element of this embodiment is produced on a translucent substrate.
- the light-transmitting substrate is a substrate that supports the organic EL element, and is preferably a smooth substrate having a light transmittance in the visible region of 400 nm to 700 nm of 50% or more.
- a glass plate, a polymer plate, etc. are mentioned.
- the glass plate include glass plates made of soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz and the like as raw materials.
- the polymer board which uses a polycarbonate, an acryl, a polyethylene terephthalate, polyether sulfide, polysulfone etc. as a raw material can be mentioned.
- the anode of the organic EL element plays a role of injecting holes into the hole transport layer or the light emitting layer, and it is effective to use a material having a work function of 4.5 eV or more.
- Specific examples of the anode material include indium tin oxide alloy (ITO), tin oxide (NESA), indium zinc oxide, gold, silver, platinum, copper, and the like.
- the anode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. When light emitted from the light emitting layer is extracted from the anode, it is preferable that the transmittance of light in the visible region of the anode is greater than 10%.
- the sheet resistance of the anode is preferably several hundred ⁇ / ⁇ (ohm / square) or less.
- the film thickness of the anode depends on the material, but is usually selected in the range of 10 nm to 1 ⁇ m, preferably 10 nm to 200 nm.
- the cathode plays a role of injecting electrons into the electron injection layer, the electron transport layer or the light emitting layer, and is preferably formed of a material having a small work function.
- the cathode material is not particularly limited, and specifically, indium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-lithium alloy, aluminum-scandium-lithium alloy, magnesium-silver alloy and the like can be used.
- the cathode can be produced by forming a thin film by a method such as vapor deposition or sputtering. Moreover, you may take out light emission from the cathode side as needed.
- An organic layer having a light emitting function which includes a host and a dopant when a doping system is employed.
- the host mainly has the function of encouraging recombination of electrons and holes and confining excitons in the light emitting layer, and the dopant has the function of efficiently emitting the excitons obtained by recombination.
- the host mainly has a function of confining excitons generated by the dopant in the light emitting layer.
- the light emitting layer employs a double host (also referred to as a host and a cohost) that adjusts the carrier balance in the light emitting layer, for example, by combining an electron transporting host and a hole transporting host. Also good. Moreover, you may employ
- the above light-emitting layer is a laminate in which a plurality of light-emitting layers are stacked, so that electrons and holes are accumulated at the light-emitting layer interface, and the recombination region is concentrated at the light-emitting layer interface to improve quantum efficiency. Can do.
- the ease of injecting holes into the light emitting layer may be different from the ease of injecting electrons, and the hole transport ability and electron transport ability expressed by the mobility of holes and electrons in the light emitting layer may be different. May be different.
- the light emitting layer can be formed by a known method such as a vapor deposition method, a spin coating method, or an LB method (Langmuir Broadgett method).
- the light emitting layer can also be formed by thinning a solution obtained by dissolving a binder such as a resin and a material compound in a solvent by a spin coating method or the like.
- the light emitting layer is preferably a molecular deposited film.
- the molecular deposition film is a thin film formed by deposition from a material compound in a gas phase state or a film formed by solidification from a material compound in a solution state or a liquid phase state. Normally, this molecular deposited film can be distinguished from a thin film (molecular accumulation film) formed by the LB method by a difference in aggregate structure, a difference in higher order structure, or a functional difference resulting therefrom.
- Examples of the dopant include a fluorescent dopant that exhibits fluorescence emission or a phosphorescence dopant that exhibits phosphorescence emission.
- the phosphorescent dopant that forms the light-emitting layer is a compound that can emit light from the triplet excited state, and is not particularly limited as long as it emits light from the triplet excited state.
- An organometallic complex containing at least one metal and a ligand is preferable.
- the ligand preferably has an ortho metal bond.
- a metal complex containing a metal atom selected from Ir, Os and Pt is preferable in that the phosphorescent quantum yield is high and the external quantum efficiency of the organic EL device can be further improved, and an iridium complex, an osmium complex, platinum Metal complexes such as complexes and orthometalated complexes are more preferred, iridium complexes and platinum complexes are more preferred, and orthometalated iridium complexes are even more preferred.
- the content of the phosphorescent dopant in the light emitting layer is not particularly limited and may be appropriately selected depending on the intended purpose. For example, it is preferably 0.1 to 70% by mass, and more preferably 1 to 30% by mass. If the phosphorescent dopant content is 0.1% by mass or more, sufficient light emission can be obtained, and if it is 70% by mass or less, concentration quenching can be avoided. Specific examples of preferred organometallic complexes as phosphorescent dopants are shown below.
- the phosphorescent host is a compound having a function of efficiently emitting the phosphorescent dopant by efficiently confining the triplet energy of the phosphorescent dopant in the light emitting layer.
- the emission wavelength of the phosphorescent dopant material contained in the light emitting layer is not particularly limited.
- at least one of the phosphorescent dopant materials contained in the light emitting layer preferably has a peak emission wavelength of 490 nm to 700 nm, and more preferably 490 nm to 650 nm.
- a luminescent color of a light emitting layer red, yellow, and green are preferable, for example.
- compounds suitable as a phosphorescent host include carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted Chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidene compounds, porphyrin compounds, anthraquinodimethane derivatives, anthrone derivatives, diphenyl Quinone derivatives, thiopyrandioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, naphth Various metal complex polys
- the organic EL element of the present embodiment may have a light emitting layer containing a fluorescent light emitting material, that is, a fluorescent light emitting layer.
- a fluorescent light emitting layer known fluorescent light emitting materials can be used.
- the fluorescent material is preferably at least one selected from anthracene derivatives, fluoranthene derivatives, styrylamine derivatives and arylamine derivatives, and more preferably anthracene derivatives and arylamine derivatives.
- the host material is more preferably an anthracene derivative, and the dopant is preferably an arylamine derivative.
- suitable materials described in International Publication No. 2010/134350 and International Publication No. 2010/134352 are selected.
- the compound and organic EL device material of the present embodiment described above may be used as a fluorescent light emitting material for the fluorescent light emitting layer, or may be used as a host for the fluorescent light emitting layer.
- the ring-forming carbon number of the anthracene derivative as the fluorescent light-emitting material is preferably 26 to 100, more preferably 26 to 80, and still more preferably 26 to 60. More specifically, the anthracene derivative is preferably an anthracene derivative represented by the following formula (10).
- Ar 31 and Ar 32 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a heterocyclic group having 5 to 50 ring atoms.
- R 81 to R 88 each independently represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, substituted or unsubstituted A substituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted ring carbon number of 6 to 50 aryloxy groups, substituted or unsubstituted arylthio groups having 6 to 50 ring carbon atoms, substituted or unsub
- the aryl group having 6 to 50 ring carbon atoms is preferably an aryl group having 6 to 40 ring carbon atoms, and more preferably an aryl group having 6 to 30 ring carbon atoms.
- the heterocyclic group having 5 to 50 ring atoms is preferably a heterocyclic group having 5 to 40 ring atoms, and more preferably a heterocyclic group having 5 to 30 ring atoms.
- the alkyl group having 1 to 50 carbon atoms is preferably an alkyl group having 1 to 30 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, and further preferably an alkyl group having 1 to 5 carbon atoms.
- the alkoxy group having 1 to 50 carbon atoms is preferably an alkoxy group having 1 to 30 carbon atoms, more preferably an alkoxy group having 1 to 10 carbon atoms, and further preferably an alkoxy group having 1 to 5 carbon atoms.
- the aralkyl group having 7 to 50 carbon atoms is preferably an aralkyl group having 7 to 30 carbon atoms, and more preferably an aralkyl group having 7 to 20 carbon atoms.
- the aryloxy group having 6 to 50 ring carbon atoms is preferably an aryloxy group having 6 to 40 ring carbon atoms, and more preferably an aryloxy group having 6 to 30 ring carbon atoms.
- the arylthio group having 6 to 50 ring carbon atoms is preferably an arylthio group having 6 to 40 ring carbon atoms, and more preferably an arylthio group having 6 to 30 ring carbon atoms.
- the alkoxycarbonyl group having 2 to 50 carbon atoms is preferably an alkoxycarbonyl group having 2 to 30 carbon atoms, more preferably an alkoxycarbonyl group having 2 to 10 carbon atoms, and further preferably an alkoxycarbonyl group having 2 to 5 carbon atoms.
- the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom.
- Ar 31 and Ar 32 are preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
- the anthracene derivative represented by the formula (10) is preferably an anthracene derivative represented by the following formula (10-1).
- Ar 33 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a heterocyclic group having 5 to 50 ring atoms.
- R 81 to R 88 are R 89 is the same as defined for R 81 to R 88.
- a is an integer of 1 to 7.
- the preferred embodiments of R 81 to R 88 are the same as described above.
- the preferred embodiment of R 89 is also the same as R 81 to R 88 .
- a is preferably an integer of 1 to 3, and more preferably 1 or 2.
- the aryl group having 6 to 50 ring carbon atoms represented by Ar 33 is preferably an aryl group having 6 to 40 ring carbon atoms, more preferably an aryl group having 6 to 30 ring carbon atoms, and 6 to 6 ring forming carbon atoms.
- An aryl group having 20 aryl groups is more preferable, and an aryl group having 6 to 12 ring carbon atoms is still more preferable.
- the arylamine derivative as the fluorescent light-emitting material is preferably an aryldiamine derivative, more preferably an aryldiamine derivative containing a pyrene skeleton, and further preferably an aryldiamine derivative containing a pyrene skeleton and a dibenzofuran skeleton. More specifically, the aryldiamine derivative is preferably an aryldiamine derivative represented by the following formula (11).
- Ar 34 to Ar 37 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
- L 21 represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 50 ring atoms.
- the aryl group having 6 to 50 ring carbon atoms is preferably an aryl group having 6 to 30 ring carbon atoms, more preferably an aryl group having 6 to 20 ring carbon atoms, and an aryl group having 6 to 12 ring carbon atoms. Group is more preferable, and phenyl group and naphthyl group are still more preferable.
- the heteroaryl group having 5 to 50 ring atoms is preferably a heteroaryl group having 5 to 40 ring atoms, more preferably a heteroaryl group having 5 to 30 ring atoms, and 5 to 5 ring forming atoms. More preferred are 20 heteroaryl groups.
- heteroaryl group examples include a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and the like, and a dibenzofuranyl group is preferable.
- substituents for the heteroaryl group include aryl groups having 6 to 30 ring carbon atoms (preferably 6 to 20, more preferably 6 to 12), and more preferably a phenyl group and a naphthyl group.
- the arylene group having 6 to 50 ring carbon atoms is preferably an arylene group having 6 to 40 ring carbon atoms, more preferably an arylene group having 6 to 30 ring carbon atoms, and an arylene group having 6 to 20 ring carbon atoms.
- a group is more preferable, and a pyrenyl group is still more preferable.
- the thickness of the light emitting layer is preferably 5 to 50 nm, more preferably 7 to 50 nm, and still more preferably 10 to 50 nm.
- the thickness is 5 nm or more, it is easy to form a light emitting layer, and when the thickness is 50 nm or less, an increase in driving voltage can be avoided.
- the hole transport layer is an organic layer formed between the light emitting layer and the anode, and has a function of transporting holes from the anode to the light emitting layer.
- an organic layer close to the anode may be defined as a hole injection layer.
- the hole injection layer has a function of efficiently injecting holes from the anode into the organic layer.
- an aromatic amine compound for example, an aromatic amine derivative represented by the following formula (H) is preferably used.
- Ar 1 to Ar 4 represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a condensed aromatic hydrocarbon group, a substituted or unsubstituted ring forming atom number of 5 to 50 aromatic heterocyclic groups or condensed aromatic heterocyclic groups, or a group in which these aromatic hydrocarbon groups or condensed aromatic hydrocarbon groups and aromatic heterocyclic groups or condensed aromatic heterocyclic groups are bonded.
- L represents a substituted or unsubstituted aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring forming atom number of 5 to 50. Represents an aromatic heterocyclic group or a condensed aromatic heterocyclic group.
- an aromatic amine of the following formula (J) is also preferably used for forming the hole transport layer.
- the hole transport layer of the organic EL device of this embodiment may have a two-layer structure of a first hole transport layer (anode side) and a second hole transport layer (cathode side).
- the thickness of the hole transport layer is not particularly limited, but is preferably 10 to 200 nm.
- a layer containing an acceptor material may be bonded to the positive hole transport layer or the anode side of the first hole transport layer. This is expected to reduce drive voltage and manufacturing costs.
- the acceptor material a compound represented by the following formula (K) is preferable.
- 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, provided that one or more pairs of R 21 and R 22 , R 23 and R 24 , and R 25 and R 26 are combined together.
- a group represented by —CO—O—CO— may be formed.
- 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 thickness of the layer containing the acceptor material is not particularly limited, but is preferably 5 to 20 nm.
- n doping is a method of doping a metal such as Li or Cs into an electron transport material
- p doping is F 4 TCNQ (2, 3, 5, 6) as a hole transport material.
- 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, a material having both electron transport properties and hole transport properties is preferable. 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.
- the same material as that used for the hole transport layer is used.
- the organic EL device of this embodiment preferably has a barrier layer such as an electron barrier layer, a hole barrier layer, or a triplet barrier layer in a portion adjacent to the light emitting layer.
- the electron barrier layer is a layer that prevents electrons from leaking from the light emitting layer to the hole transport layer
- the hole barrier layer is a layer that prevents holes from leaking from the light emitting layer to the electron transport layer. is there.
- the triplet barrier layer prevents the triplet excitons generated in the light emitting layer from diffusing into the surrounding layers, and confins the triplet excitons in the light emitting layer, thereby transporting electrons other than the light emitting dopant of the triplet excitons. It has a function of suppressing energy deactivation on the molecules of the layer.
- the triplet energy of the phosphorescent dopant in the light emitting layer is E T d and the triplet energy of the compound used as the triplet barrier layer is E T TB , E T d ⁇ If the energy magnitude relationship of E T TB is satisfied, the triplet exciton of the phosphorescent dopant is confined (cannot move to other molecules) and the energy deactivation path other than light emission on the dopant is interrupted. It is assumed that light can be emitted with high efficiency.
- the electron mobility of the material constituting the triplet barrier layer is preferably 10 ⁇ 6 cm 2 / (V ⁇ s) or more in the range of electric field strength of 0.04 to 0.5 MV / cm.
- a method for measuring the electron mobility of an organic material several methods such as the Time of Flight method are known.
- the electron mobility is determined by impedance spectroscopy.
- the electron injection layer is desirably 10 ⁇ 6 cm 2 / (V ⁇ s) or more in the range of electric field strength of 0.04 to 0.5 MV / cm. This facilitates the injection of electrons from the cathode into the electron transport layer, and also promotes the injection of electrons into the adjacent barrier layer and the light emitting layer, thereby enabling driving at a lower voltage.
- the method for forming each layer of the organic EL element of the present embodiment is not limited except as specifically mentioned above, but a dry film forming method such as a vacuum evaporation method, a sputtering method, a plasma method, an ion plating method, a spin method, Known methods such as a coating method, a dipping method, a flow coating method, and a wet film forming method such as an ink jet method can be employed.
- the film thickness of each organic layer of the organic EL element of the present embodiment is not limited except as specifically mentioned above. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and conversely, if it is too thick, it is high. Since an applied voltage is required and the efficiency is deteriorated, the range of several nm to 1 ⁇ m is usually preferable.
- the organic EL element according to the present embodiment can be used for display devices such as an organic EL panel module, display devices such as a television, a mobile phone, a tablet, or a personal computer, and electronic devices such as lighting or a light emitting device for a vehicle lamp. .
- the compound according to the embodiment represented by the general formula (1) or the like is not limited to the mode used for the electron injection layer 8 of the organic EL element 1, but is used for other organic layers. Also good.
- the electron transport layer 7 contains the compound according to the embodiment.
- the electron transport layer 7 preferably further includes at least one of an electron donating dopant and an organometallic complex.
- the specific structure and shape in the implementation of the present invention may be other structures as long as the object of the present invention can be achieved.
- Example 1 A 25 mm ⁇ 75 mm ⁇ 1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes.
- the glass substrate with the transparent electrode line after washing is attached to the substrate holder of the vacuum evaporation apparatus, and the compound (HI-1) is first coated so as to cover the transparent electrode on the surface on which the transparent electrode line is formed.
- a HI-1 film having a thickness of 10 nm was formed by evaporation to form a hole injection layer.
- the above compound (HT-1) is deposited as a first hole transport material to form an HT-1 film having a thickness of 80 nm, thereby forming a first hole transport layer.
- the compound (HT-2) was deposited on the first hole transport layer to form an HT-2 film having a thickness of 10 nm, thereby forming a second hole transport layer.
- the compound (BH-1) as a host material and the compound (BD-1) as a dopant material are co-deposited on the HT-2 film at a weight ratio of 24: 1 with a thickness of 25 nm. Thus, a light emitting layer was obtained.
- the compound (HB-1) was deposited on this light emitting layer to form a 25 nm thick HB-1 film, and a hole blocking layer and an electron transporting layer were formed. Further, the compound (1) synthesized in Synthesis Example 1 was deposited to form an electron injection layer having a thickness of 10 nm. Thereafter, LiF was formed to a thickness of 1 nm, and a metal cathode was formed by vapor-depositing metal Al on the LiF film to a thickness of 150 nm, thereby manufacturing an organic EL element.
- Example 2 an organic EL device was prepared and evaluated in the same manner except that the compound shown in Table 1 was used instead of the compound (1).
- the organic EL element can be reduced in voltage and efficiency.
- the organic EL devices of Examples 1 to 3 using a compound having a nitrogen-containing heterocyclic group at the terminal operate with lower voltage and higher efficiency.
- the compounds (1) to (3) which are compounds according to an embodiment of the present invention, have improved electron injection properties due to the terminal nitrogen-containing heterocyclic group represented by Az in the general formula (1). It is.
- simply replacing the terminal phenyl group of compound E-1 of Comparative Example 1 with a nitrogen-containing heterocyclic group greatly improves the performance as an electron transporting material. That is, it can be seen that the use of the compounds (1) to (3) improved the performance of the organic EL device in terms of driving voltage and light emission efficiency as compared with the case of using the compound (E-1). .
- Example 4 A 25 mm ⁇ 75 mm ⁇ 1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes.
- the glass substrate with the transparent electrode line after washing is attached to the substrate holder of the vacuum evaporation apparatus, and the compound (HI-1) is first coated so as to cover the transparent electrode on the surface on which the transparent electrode line is formed.
- a HI-1 film having a thickness of 5 nm was formed by vapor deposition to form a hole injection layer.
- the above compound (HT-1) is deposited as a first hole transport material to form an HT-1 film having a thickness of 80 nm, thereby forming a first hole transport layer.
- the compound (HT-2) was deposited on the first hole transport layer to form an HT-2 film having a thickness of 10 nm, thereby forming a second hole transport layer.
- the following compound (BH-2) as a host material and the following compound (BD-2) as a dopant material are co-deposited on the HT-2 film at a weight ratio of 24: 1 with a thickness of 25 nm.
- a light emitting layer was obtained.
- the compound (4) synthesized in Synthesis Example 4 was deposited on this light emitting layer to form a compound (4) film having a film thickness of 25 nm to form an electron transport layer. Then, LiF was formed into a film with a thickness of 1 nm, and an organic EL element was manufactured by depositing metal Al on the LiF film to a thickness of 80 nm to form a metal cathode.
- Example 5 The organic EL device of Example 5 was produced in the same manner as in Example 4 except that the compound (5) synthesized in Synthesis Example 5 was used instead of the compound (4) in Example 4.
- Comparative example 2 The organic EL device of Comparative Example 2 was produced in the same manner as in Example 4 except that the following compound (E-2) was used instead of the compound (4) in Example 4.
- the organic EL element can be reduced in voltage and efficiency.
- the organic EL devices of Examples 4 to 5 using a compound having a nitrogen-containing heterocyclic group at the terminal operate with lower voltage and higher efficiency.
- the use of the compound (4) or the compound (5) compared with the case of using the compound (E-2) improved the performance of the organic EL device in terms of driving voltage and light emission efficiency. I understand.
- Example 6 A 25 mm ⁇ 75 mm ⁇ 1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes.
- the glass substrate with the transparent electrode line after washing is mounted on the substrate holder of the vacuum deposition apparatus, and first, the following compound HI-1 is deposited on the surface on which the transparent electrode line is formed so as to cover the transparent electrode. Then, a HI-1 film having a thickness of 5 nm was formed to form a hole injection layer.
- the compound HT-1 was deposited as a first hole transport material to form an HT-1 film having a thickness of 80 nm, thereby forming a first hole transport layer.
- the compound HT-2 was vapor-deposited on the first hole transport layer to form an HT-2 film having a thickness of 10 nm, thereby forming a fourth hole transport layer.
- the host BH-2 and the dopant BD-2 were formed by co-evaporation at a mass ratio of 24: 1 with a film thickness of 25 nm to form a light emitting layer.
- the compound (2) synthesized in Synthesis Example 2 and 8-quinolinolatolithium (Liq) were formed by co-evaporation at a mass ratio of 50:50, and the film thickness was 25 m.
- An electron transport layer was formed.
- Metal Al was vapor-deposited on this electron transport layer, and a metal cathode was formed with a film thickness of 80 nm to produce an organic EL device.
- Comparative example 3 The organic EL device of Comparative Example 3 was produced in the same manner as in Example 6 except that the following compound (E-3) was used instead of the compound (2) in Example 6.
- Example 6 For the organic EL devices produced in Example 6 and Comparative Example 3, the drive voltage was measured in the same manner as described above, and the life LT90 was measured and evaluated by the following method. The results are shown in Table 3.
- SYMBOLS 1 Organic EL element, 2 ... Substrate, 3 ... Anode, 4 ... Cathode, 5 ... Light emitting layer, 6 ... Hole injection / transport layer, 7 ... Electron transport layer, 8 ... Electron injection layer, 10 ... Organic layer, 11 ... electronic transport zone.
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Abstract
Description
R3は、それぞれ独立に、
水素原子、
ハロゲン原子、
ヒドロキシル基、
シアノ基、
置換もしくは無置換の炭素数1~30のアルキル基、
置換もしくは無置換の炭素数3~30のアルキルシリル基、
置換もしくは無置換の環形成炭素数6~60のアリールシリル基、
置換もしくは無置換の炭素数1~30のアルコキシ基、
置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、
置換もしくは無置換の炭素数2~30のアルキルアミノ基、
置換もしくは無置換の環形成炭素数6~60のアリールアミノ基、
置換もしくは無置換の炭素数1~30のアルキルチオ基、
置換もしくは無置換の環形成炭素数6~30のアリールチオ基、
置換もしくは無置換の環形成炭素数6~30の芳香族炭化水素基、又は
置換もしくは無置換の環形成原子数5~30の複素環基である。
R2は、
置換もしくは無置換の環形成炭素数6~30の芳香族炭化水素基である。
R2が置換基を有する場合、置換基は、
ハロゲン原子、
ヒドロキシル基、
シアノ基、
ニトロ基、
カルボキシ基、
置換もしくは無置換の炭素数2~30のアルキル基、
置換もしくは無置換の炭素数2~30のアルケニル基、
置換もしくは無置換の炭素数1~30のアルキニル基、
置換もしくは無置換の炭素数3~30のアルキルシリル基、
置換もしくは無置換の環形成炭素数6~60のアリールシリル基、
置換もしくは無置換の炭素数1~30のアルコキシ基、
置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、
置換もしくは無置換の環形成炭素数6~30のアリールチオ基、
置換もしくは無置換の環形成炭素数5~30の含酸素複素環基、
置換もしくは無置換の環形成炭素数5~30の含硫黄複素環基、又は
置換もしくは無置換の環形成炭素数6~30の芳香族炭化水素基である。
前記アリールオキシ基および前記アリールチオ基が置換基を有する場合、隣接する置換基が結合して環を形成する場合と環を形成しない場合とがある。
L1は、単結合または連結基であり、L1における連結基としては、
アルケニレン基、
アルキニレン基、
置換もしくは無置換の環形成炭素数6~30の芳香族炭化水素基、
置換もしくは無置換の環形成原子数5~30の複素環基、
前記芳香族炭化水素基から選ばれる2個から4個の基が結合してなる多重連結基、
前記複素環基から選ばれる2個から4個の基が結合してなる多重連結基、又は
前記芳香族炭化水素基及び前記複素環基から選ばれる2個から4個の基が結合してなる多重連結基である。
なお、前記多重連結基を構成する前記芳香族炭化水素基および前記複素環基は、互いに同一または異なり、隣り合う基が結合してさらに環を形成する場合と、環を形成しない場合とがある。
L2は、連結基であり、連結基としては、L1における連結基と同義である。
nおよびmは、それぞれ独立に1以上5以下の整数である。
nが2以上5以下の整数である場合、複数のCzは、互いに同一であるか、または異なる。
mが2以上5以下の整数である場合、複数のAzは、互いに同一であるか、または異なる。
Czは、下記一般式(1a)で表され、
Azは、下記一般式(11)で表される。)
X1~X8は、それぞれ独立にCRまたは窒素原子である。
RおよびR1は、それぞれ独立に、
水素原子、
ハロゲン原子、
ヒドロキシル基、
シアノ基、
置換もしくは無置換の炭素数1~30のアルキル基、
置換もしくは無置換の炭素数3~30のアルキルシリル基、
置換もしくは無置換の環形成炭素数6~60のアリールシリル基、
置換もしくは無置換の炭素数1~30のアルコキシ基、
置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、
置換もしくは無置換の炭素数2~30のアルキルアミノ基、
置換もしくは無置換の環形成炭素数6~60のアリールアミノ基、
置換もしくは無置換の炭素数1~30のアルキルチオ基、
置換もしくは無置換の環形成炭素数6~30のアリールチオ基、
置換もしくは無置換の環形成炭素数6~30の芳香族炭化水素基、又は
置換もしくは無置換の環形成原子数5~30の複素環基である。
互いに隣接するRが結合して、環を形成する場合と、環を形成しない場合とがある。
Rが複数ある場合、複数のRは、互いに同一、または異なる。
ただし、RおよびR1のいずれか1つは、前記一般式(1)のL1に結合する単結合である。
また、R1と隣接するRとが互いに結合して、環を形成する場合と、環を形成しない場合とがある。)
X9は、CR9または窒素原子であり、X10は、CR10または窒素原子である。
R4~R6,R9およびR10は、それぞれ独立に、
水素原子、
ハロゲン原子、
ヒドロキシル基、
シアノ基、
置換もしくは無置換の炭素数1~30のアルキル基、
置換もしくは無置換の炭素数3~30のアルキルシリル基、
置換もしくは無置換の環形成炭素数6~60のアリールシリル基、
置換もしくは無置換の炭素数1~30のアルコキシ基、
置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、
置換もしくは無置換の炭素数2~30のアルキルアミノ基、
置換もしくは無置換の環形成炭素数6~60のアリールアミノ基、
置換もしくは無置換の炭素数1~30のアルキルチオ基、又は
置換もしくは無置換の環形成炭素数6~30のアリールチオ基である。
R4~R6,R9およびR10のうち隣り合う基が結合してさらに環を形成する場合と、環を形成しない場合とがある。
ただし、R4~R6,R9およびR10のうちいずれか1つは、L2に結合する単結合である。)
本発明の一実施形態に係る化合物は、下記一般式(1)で表されることを特徴とする。
水素原子、
ハロゲン原子、
ヒドロキシル基、
シアノ基、
置換もしくは無置換の炭素数1~30のアルキル基、
置換もしくは無置換の炭素数3~30のアルキルシリル基、
置換もしくは無置換の環形成炭素数6~60のアリールシリル基、
置換もしくは無置換の炭素数1~30のアルコキシ基、
置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、
置換もしくは無置換の炭素数2~30のアルキルアミノ基、
置換もしくは無置換の環形成炭素数6~60のアリールアミノ基、
置換もしくは無置換の炭素数1~30のアルキルチオ基、
置換もしくは無置換の環形成炭素数6~30のアリールチオ基、
置換もしくは無置換の環形成炭素数6~30の芳香族炭化水素基、又は
置換もしくは無置換の環形成原子数5~30の複素環基である。
R2は、置換もしくは無置換の環形成炭素数6~30の芳香族炭化水素基である。
R2が置換基を有する場合、置換基は、
ハロゲン原子、
ヒドロキシル基、
シアノ基、
ニトロ基、
カルボキシ基、
置換もしくは無置換の炭素数1~30のアルキル基、
置換もしくは無置換の炭素数2~30のアルケニル基、
置換もしくは無置換の炭素数2~30のアルキニル基、
置換もしくは無置換の炭素数3~30のアルキルシリル基、
置換もしくは無置換の環形成炭素数6~60のアリールシリル基、
置換もしくは無置換の炭素数1~30のアルコキシ基、
置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、
置換もしくは無置換の環形成炭素数6~30のアリールチオ基、
置換もしくは無置換の環形成炭素数5~30の含酸素複素環基、
置換もしくは無置換の環形成炭素数5~30の含硫黄複素環基、又は
置換もしくは無置換の環形成炭素数6~30の芳香族炭化水素基である。
前記アリールオキシ基および前記アリールチオ基が置換基を有する場合、隣接する置換基が結合して環を形成する場合と環を形成しない場合とがある。
L1は、単結合または連結基であり、L1における連結基としては、
アルケニレン基、
アルキニレン基、
置換もしくは無置換の環形成炭素数6~30の芳香族炭化水素基、
置換もしくは無置換の環形成原子数5~30の複素環基、
前記芳香族炭化水素基から選ばれる2個から4個の基が結合してなる多重連結基、
前記複素環基から選ばれる2個から4個の基が結合してなる多重連結基、又は
前記芳香族炭化水素基及び前記複素環基から選ばれる2個から4個の基が結合してなる多重連結基である。
なお、前記多重連結基を構成する前記芳香族炭化水素基および前記複素環基は、互いに同一または異なり、隣り合う基が結合してさらに環を形成する場合と、環を形成しない場合とがある。
L2は、連結基であり、連結基としては、L1における連結基と同義である。
nおよびmは、それぞれ独立に1以上5以下の整数である。
nが2以上5以下の整数である場合、複数のCzは、互いに同一であるか、または異なる。
mが2以上5以下の整数である場合、複数のAzは、互いに同一であるか、または異なる。
Czは、下記一般式(1a)で表され、
Azは、下記一般式(11)で表される。)
X1~X8は、それぞれ独立にCRまたは窒素原子である。
RおよびR1は、それぞれ独立に、
水素原子、
ハロゲン原子、
ヒドロキシル基、
シアノ基、
置換もしくは無置換の炭素数1~30のアルキル基、
置換もしくは無置換の炭素数3~30のアルキルシリル基、
置換もしくは無置換の環形成炭素数6~60のアリールシリル基、
置換もしくは無置換の炭素数1~30のアルコキシ基、
置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、
置換もしくは無置換の炭素数2~30のアルキルアミノ基、
置換もしくは無置換の環形成炭素数6~60のアリールアミノ基、
置換もしくは無置換の炭素数1~30のアルキルチオ基、
置換もしくは無置換の環形成炭素数6~30のアリールチオ基、
置換もしくは無置換の環形成炭素数6~30の芳香族炭化水素基、又は
置換もしくは無置換の環形成原子数5~30の複素環基である。
互いに隣接するRが結合して、環を形成する場合と、環を形成しない場合とがある。
Rが複数ある場合、複数のRは、互いに同一、または異なる。
ただし、RおよびR1のいずれか1つは、前記一般式(1)のL1に結合する単結合である。
また、R1と隣接するRとが互いに結合して、環を形成する場合と、環を形成しない場合とがある。)
X9は、CR9または窒素原子であり、X10は、CR10または窒素原子である。
R4~R6,R9およびR10は、それぞれ独立に、
水素原子、
ハロゲン原子、
ヒドロキシル基、
シアノ基、
置換もしくは無置換の炭素数1~30のアルキル基、
置換もしくは無置換の炭素数3~30のアルキルシリル基、
置換もしくは無置換の環形成炭素数6~60のアリールシリル基、
置換もしくは無置換の炭素数1~30のアルコキシ基、
置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、
置換もしくは無置換の炭素数2~30のアルキルアミノ基、
置換もしくは無置換の環形成炭素数6~60のアリールアミノ基、
置換もしくは無置換の炭素数1~30のアルキルチオ基、又は
置換もしくは無置換の環形成炭素数6~30のアリールチオ基である。
R4~R6,R9およびR10のうち隣り合う基が結合してさらに環を形成する場合と、環を形成しない場合とがある。
ただし、R4~R6,R9およびR10のうちいずれか1つは、L2に結合する単結合である。)
ただし、前記一般式(1B)において、X1~X8のうちいずれか1つは、L1に結合する炭素原子である。)
さらに、前記Azは、下記一般式(11-a)から(11-x)までのいずれかで表される基であることが好ましく、これらの中でも、縮合環を有さない単環の構造を有する基であることがより好ましく、(11-a)から(11-g)までのいずれかで表される基であることがさらに好ましい。
なお、下記式(11-a)から(11-x)までのいずれかで表される基は、さらに置換基を有していてもよく、置換基を有する場合は、後述する「置換もしくは無置換の」という場合における置換基を有する。
なお、下記式(L-1a)から(L-1f)までのいずれかで表される基は、さらに置換基を有していてもよく、置換基を有する場合は、後述する「置換もしくは無置換の」という場合における置換基を有する。
なお、下記式(L-2a)から(L-2f)までのいずれかで表される基は、さらに置換基を有していてもよく、置換基を有する場合は、後述する「置換もしくは無置換の」という場合における置換基を有する。
なお、下記式(R-2a)から(R-2e)までのいずれかで表される基は、さらに置換基を有していてもよく、置換基を有する場合は、後述する「置換もしくは無置換の」という場合における置換基を有する。
本実施形態における芳香族炭化水素基としては、環形成炭素数が6~20であることが好ましく、6~12であることがより好ましい。上記芳香族炭化水素基の中でもフェニル基、ビフェニル基、ナフチル基、フェナントリル基、ターフェニル基、フルオレニル基がさらに好ましい。1-フルオレニル基、2-フルオレニル基、3-フルオレニル基および4-フルオレニル基については、9位の炭素原子に、後述する本実施形態における置換もしくは無置換の炭素数1~30のアルキル基、または置換もしくは無置換の環形成炭素数6~18のアリール基が置換されていることが好ましい。
また、本実施形態の第一の環構造における環形成炭素数6~24の芳香族炭化水素基としては、上記した芳香族炭化水素基のうち環形成炭素数が6~24である基を用いることができる。
本実施形態における環形成原子数5~30の複素環基としては、例えば、ピリジル基、ピリミジニル基、ピラジニル基、ピリダジニル基、トリアジニル基、キノリル基、イソキノリニル基、ナフチリジニル基、フタラジニル基、キノキサリニル基、キナゾリニル基、フェナントリジニル基、アクリジニル基、フェナントロリニル基、ピロリル基、イミダゾリル基、ピラゾリル基、トリアゾリル基、テトラゾリル基、インドリル基、ベンズイミダゾリル基、インダゾリル基、イミダゾピリジニル基、ベンズトリアゾリル基、カルバゾリル基、フリル基、チエニル基、オキサゾリル基、チアゾリル基、イソキサゾリル基、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、ベンゾフラニル基、ベンゾチオフェニル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、ベンゾイソキサゾリル基、ベンゾイソチアゾリル基、ベンゾオキサジアゾリル基、ベンゾチアジアゾリル基、ジベンゾフラニル基、ジベンゾチオフェニル基、ピペリジニル基、ピロリジニル基、ピペラジニル基、モルホリル基、フェナジニル基、フェノチアジニル基、フェノキサジニル基などが挙げられる。
本実施形態における複素環基の環形成原子数は5~20であることが好ましく、5~14であることがより好ましい。上記複素環基の中でも1-ジベンゾフラニル基、2-ジベンゾフラニル基、3-ジベンゾフラニル基、4-ジベンゾフラニル基、1-ジベンゾチオフェニル基、2-ジベンゾチオフェニル基、3-ジベンゾチオフェニル基、4-ジベンゾチオフェニル基、1-カルバゾリル基、2-カルバゾリル基、3-カルバゾリル基、4-カルバゾリル基、9-カルバゾリル基がさらに好ましい。1-カルバゾリル基、2-カルバゾリル基、3-カルバゾリル基および4-カルバゾリル基については、9位の窒素原子に、本実施形態における置換もしくは無置換の環形成炭素数6~30の芳香族炭化水素基または置換もしくは無置換の環形成原子数5~30の複素環基が置換されていることが好ましい。
また、本実施形態の第一の環構造における環形成原子数6~24の複素環基としては、上記した複素環基のうち環形成原子数が6~24である基を用いることができる。
本実施形態における直鎖または分岐鎖のアルキル基の炭素数は、1~10であることが好ましく、1~6であることがより好ましい。上記直鎖または分岐鎖のアルキル基の中でもメチル基、エチル基、プロピル基、イソプロピル基、n-ブチル基、s-ブチル基、イソブチル基、t-ブチル基、n-ペンチル基、n-ヘキシル基、アミル基、イソアミル基、ネオペンチル基がさらに好ましい。
本実施形態におけるシクロアルキル基としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、4-メチルシクロヘキシル基、アダマンチル基、ノルボルニル基等が挙げられる。シクロアルキル基の環形成炭素数は、3~10であることが好ましく、5~8であることがより好ましい。上記シクロアルキル基の中でも、シクロペンチル基やシクロヘキシル基がさらに好ましい。
アルキル基がハロゲン原子で置換されたハロゲン化アルキル基としては、例えば、上記炭素数1~30のアルキル基が1以上のハロゲン基で置換された基が挙げられる。具体的には、フルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、フルオロエチル基、トリフルオロメチルメチル基、トリフルオロエチル基、ペンタフルオロエチル基等が挙げられる。
ジアルキルアリールシリル基は、例えば、上記炭素数1~30のアルキル基で例示したアルキル基を2つ有し、上記環形成炭素数6~30の芳香族炭化水素基を1つ有するジアルキルアリールシリル基が挙げられる。ジアルキルアリールシリル基の炭素数は、8~30であることが好ましい。
アルキルジアリールシリル基は、例えば、上記炭素数1~30のアルキル基で例示したアルキル基を1つ有し、上記環形成炭素数6~30の芳香族炭化水素基を2つ有するアルキルジアリールシリル基が挙げられる。アルキルジアリールシリル基の炭素数は、13~30であることが好ましい。
トリアリールシリル基は、例えば、上記環形成炭素数6~30の芳香族炭化水素基を3つ有するトリアリールシリル基が挙げられる。トリアリールシリル基の炭素数は、18~30であることが好ましい。
アルコキシ基がハロゲン原子で置換されたハロゲン化アルコキシ基としては、例えば、上記炭素数1~30のアルコキシ基が1以上のハロゲン基で置換された基が挙げられる。
環形成炭素数6~30のアリールチオ基は、-SRWと表される。このRWの例として、上記環形成炭素数6~30の芳香族炭化水素基が挙げられる。
本実施形態において、環形成原子数とは、原子が環状に結合した構造(例えば単環、縮合環、環集合)の化合物(例えば単環化合物、縮合環化合物、架橋化合物、炭素環化合物、複素環化合物)の当該環自体を構成する原子の数を表す。環を構成しない原子(例えば環を構成する原子の結合手を終端する水素原子)や、当該環が置換基によって置換される場合の置換基に含まれる原子は環形成原子数には含まない。以下で記される「環形成原子数」については、特筆しない限り同様とする。例えば、ピリジン環は、環形成原子数が6であり、キナゾリン環は、環形成原子数が10であり、フラン環は、環形成原子数が5である。ピリジン環やキナゾリン環の炭素原子にそれぞれ結合している水素原子や置換基を構成する原子については、環形成原子数の数に含めない。また、フルオレン環に置換基として例えばフルオレン環が結合している場合(スピロフルオレン環を含む)、置換基としてのフルオレン環の原子数は環形成原子数の数に含めない。
ここで挙げた置換基の中では、芳香族炭化水素基、複素環基、アルキル基、ハロゲン原子、アルキルシリル基、アリールシリル基、シアノ基が好ましく、さらには、各置換基の説明において好ましいとした具体的な置換基が好ましい。
本明細書において、「置換もしくは無置換の」という場合における「無置換」とは前記置換基で置換されておらず、水素原子が結合していることを意味する。
なお、本明細書において、「置換または無置換の炭素数XX~YYのZZ基」という表現における「炭素数XX~YY」は、ZZ基が無置換である場合の炭素数を表し、置換されている場合の置換基の炭素数は含めない。ここで、「YY」は「XX」よりも大きく、「XX」と「YY」はそれぞれ1以上の整数を意味する。
本実施形態において、「置換または無置換の原子数XX~YYのZZ基」という表現における「原子数XX~YY」は、ZZ基が無置換である場合の原子数を表し、置換されている場合の置換基の原子数は含めない。ここで、「YY」は「XX」よりも大きく、「XX」と「YY」はそれぞれ1以上の整数を意味する。
以下に説明する化合物またはその部分構造において、「置換もしくは無置換の」という場合についても、前記と同様である。
ただし、前記一般式(1)、(1A)、(1B)、(12A-1)、(12A-2)、(12B-1)、(12B-2)、(13A)、および(15A)において、R2が置換基を有する場合、すなわち、置換のXX基である場合の置換基は、ハロゲン原子、ヒドロキシル基、シアノ基、ニトロ基、カルボキシ基、置換もしくは無置換の炭素数1~30のアルキル基、置換もしくは無置換の炭素数1~30のアルケニル基、置換もしくは無置換の炭素数1~30のアルキニル基、置換もしくは無置換の炭素数3~30のアルキルシリル基、置換もしくは無置換の環形成炭素数6~60のアリールシリル基、置換もしくは無置換の炭素数1~30のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数5~30の含酸素複素環基、置換もしくは無置換の環形成炭素数5~30の含硫黄複素環基、又は置換もしくは無置換の環形成炭素数6~30の芳香族炭化水素基であり、前記アリールオキシ基および前記アリールチオ基が置換基を有する場合、隣接する置換当該置換基が結合して環を形成する場合と環を形成しない場合とがある。
本実施形態の化合物は、有機EL素子用材料として用いることができる。この場合、本実施形態の化合物を単独で有機EL素子用材料としてもよいし、本実施形態の化合物を他の材料とともに用いて有機EL素子用材料としてもよい。
本発明の一実施形態における有機EL素子は、陰極と、陽極と、陰極と陽極との間に配置された有機層とを有する。有機層は、少なくとも発光層を含む複数層で構成される。
本実施形態の有機EL素子において、有機層は、少なくとも発光層を含み、電子輸送帯域を含む。電子輸送帯域は、発光層と陰極との間に設けられた層であって、電子輸送帯域は、少なくとも電子注入層を含み、電子注入層と電子輸送層とを含んでいてもよく、さらに正孔障壁層やスペース層を含んでいてもよい。これらの層のほかに、さらに、正孔注入層、正孔輸送層、電子障壁層等の公知の有機EL素子で採用される層を有していてもよい。有機層は、無機化合物を含んでいてもよい。
(1)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。発光ユニットの代表的な層構成を以下に示す。
(a)正孔輸送層/発光層(/電子輸送層)
(b)正孔輸送層/第一燐光発光層/第二燐光発光層(/電子輸送層)
(c)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)
(d)正孔輸送層/第一燐光発光層/第二燐光発光層/スペース層/蛍光発光層(/電子輸送層)
(e)正孔輸送層/第一燐光発光層/スペース層/第二燐光発光層/スペース層/蛍光発光層(/電子輸送層)
(f)正孔輸送層/燐光発光層/スペース層/第一蛍光発光層/第二蛍光発光層(/電子輸送層)
(g)正孔輸送層/電子障壁層/発光層(/電子輸送層)
(h)正孔輸送層/発光層/正孔障壁層(/電子輸送層)
(i)正孔輸送層/蛍光発光層/トリプレット障壁層(/電子輸送層)
尚、各発光層と正孔輸送層との間、あるいは各発光層と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、寿命を向上させることができる。
(2)陽極/第一発光ユニット/中間層/第二発光ユニット/陰極
ここで、上記第一発光ユニット及び第二発光ユニットとしては、例えば、それぞれ独立に上述の発光ユニットと同様の発光ユニットを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、または中間絶縁層とも呼ばれ、第一発光ユニットに電子を、第二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。
図1に示す有機EL素子1は、基板2と、陽極3と、陰極4と、陽極3と陰極4との間に配置された有機層10と、を有する。
そして、有機層10は、陽極3側から順に、正孔注入・輸送層6、発光層5、電子輸送層7、および電子注入層8が積層されて構成される。このうち、電子輸送層7と電子注入層8が電子輸送帯域11を構成している。
本実施形態の有機EL素子1における、電子輸送帯域11は、前記した本発明の一実施形態に係る化合物を含むことが好ましい。本実施形態においては、電子輸送帯域11は、電子輸送層7と電子注入層8とを含む。本発明の一実施形態に係る化合物は、電子輸送帯域11のいずれの層に含まれていてもよいが、本実施形態においては、電子注入層8に含まれる。
なお、本実施形態における電子輸送帯域11は、後述する電子供与性ドーパントを含有していても好ましい。
電子注入層は、陰極から電子を効率的に有機層ユニットに注入する機能を有する。電子輸送帯域が複数層で構成される場合、陰極に近い有機層を電子注入層とする。本実施形態の電子注入層8は、前記した本発明の一実施形態に係る化合物を含む。すなわち、前記一般式(1)、(1A)、(1B)、(13A)、(15A)~(16A)、(12A-1)~(12A-2)、および(12B-1)~(12B-2)のいずれかで表される化合物を含む。
電子輸送層7は、発光層と陰極との間に形成される有機層であって、電子を陰極から発光層へ輸送する機能を有する。前記した本発明の一実施形態に係る化合物および有機EL素子用材料は、電子輸送層を形成する電子輸送層用材料としても好適である。
この含窒素環誘導体としては、例えば、下記式(A)で表される含窒素環金属キレート錯体が好ましい。
置換されていてもよいアミノ基の例としては、アルキルアミノ基、アリールアミノ基、アラルキルアミノ基が挙げられる。
アルキルアミノ基及びアラルキルアミノ基は-NQ1Q2と表される。Q1及びQ2は、それぞれ独立に、炭素数1~20のアルキル基又は炭素数1~20のアラルキル基を表す。Q1及びQ2の一方は水素原子であってもよい。
アリールアミノ基は-NAr1Ar2と表され、Ar1及びAr2は、それぞれ独立に、炭素数6~50の非縮合芳香族炭化水素基又は縮合芳香族炭化水素基を表す。Ar1及びAr2の一方は水素原子であってもよい。
アルコキシカルボニル基は-COOY’と表され、Y’は炭素数1~20のアルキル基を表す。
Mは、アルミニウム(Al)、ガリウム(Ga)又はインジウム(In)であり、Inであると好ましい。
Lは、下記式(A’)又は(A”)で表される基である。
HAr-L1-Ar1-Ar2 (D1)
前記式(D1)中、HArは、置換もしくは無置換の炭素数3~40の含窒素複素環基であり、L1は単結合、置換もしくは無置換の炭素数6~40の芳香族炭化水素基又は縮合芳香族炭化水素基又は置換もしくは無置換の炭素数3~40の芳香族複素環基又は縮合芳香族複素環基であり、Ar1は置換もしくは無置換の炭素数6~40の2価の芳香族炭化水素基であり、Ar2は置換もしくは無置換の炭素数6~40の芳香族炭化水素基又は縮合芳香族炭化水素基又は置換もしくは無置換の炭素数3~40の芳香族複素環基又は縮合芳香族複素環基である。
R1及びR2は、それぞれ独立に、置換もしくは無置換の環形成炭素数6~50のアリール基、置換もしくは無置換の環形成原子数5~50のヘテロアリール基、置換もしくは無置換の炭素数1~20のアルキル基、置換もしくは無置換の炭素数1~20のハロアルキル基又は置換もしくは無置換の炭素数1~20のアルコキシ基である。
Ar1は、置換もしくは無置換の環形成炭素数6~50のアリール基又は置換もしくは無置換の環形成原子数5~50のヘテロアリール基である。
Ar2は、水素原子、置換もしくは無置換の炭素数1~20のアルキル基、置換もしくは無置換の炭素数1~20のハロアルキル基、置換もしくは無置換の炭素数1~20のアルコキシ基、置換もしくは無置換の環形成炭素数6~50のアリール基又は置換もしくは無置換の環形成原子数5~50のヘテロアリール基である。
Ar3は、置換もしくは無置換の環形成炭素数6~50のアリーレン基又は置換もしくは無置換の環形成原子数5~50のヘテロアリーレン基である。
L1、L2及びL3は、それぞれ独立に、単結合、置換もしくは無置換の環形成炭素数6~50のアリーレン基、又は置換もしくは無置換の環形成原子数9~50の2価の縮合芳香族複素環基である。
環形成原子数5~50のヘテロアリール基としては、ピロリル基、フリル基、チエニル基、シローリル基、ピリジル基、キノリル基、イソキノリル基、ベンゾフリル基、イミダゾリル基、ピリミジル基、カルバゾリル基、セレノフェニル基、オキサジアゾリル基、トリアゾリル基、ピラジニル基、ピリダジニル基、トリアジニル基、キノキサリニル基、アクリジニル基、イミダゾ[1,2-a]ピリジニル基、イミダゾ[1,2-a]ピリミジニル基等が挙げられる。
炭素数1~20のハロアルキル基としては、前記アルキル基の1又は2以上の水素原子をフッ素、塩素、ヨウ素及び臭素から選ばれる少なくとも1のハロゲン原子で置換して得られる基が挙げられる。
炭素数1~20のアルコキシ基としては、前記アルキル基をアルキル部位としては有する基が挙げられる。
環形成炭素数6~50のアリーレン基としては、前記アリール基から水素原子1個を除去して得られる基が挙げられる。
環形成原子数9~50の2価の縮合芳香族複素環基としては、前記ヘテロアリール基として記載した縮合芳香族複素環基から水素原子1個を除去して得られる基が挙げられる。
また、有機EL素子1の電子輸送帯域11は、電子注入層8の他に、第二の電子注入層を備えていてもよい。第二の電子注入層は、電子輸送層と電子注入層8との間に設けられていてもよい。第二の電子注入層の構成成分としては、含窒素環誘導体の他に無機化合物としての絶縁体又は半導体を使用することが好ましい。第二の電子注入層が絶縁体や半導体で構成されていれば、電流のリークを有効に防止して、電子注入性を向上させることができる。
本実施形態の有機EL素子は、電子輸送帯域または陰極と有機層との界面領域に電子供与性ドーパントおよび有機金属錯体の少なくともいずれかを有することも好ましい。
このような構成によれば、有機EL素子における発光輝度の向上や長寿命化が図られる。
電子供与性ドーパントとしては、アルカリ金属、アルカリ金属化合物、アルカリ土類金属、アルカリ土類金属化合物、希土類金属、および希土類金属化合物などから選ばれた少なくとも一種類が挙げられる。
有機金属錯体としては、アルカリ金属を含む有機金属錯体、アルカリ土類金属を含む有機金属錯体、および希土類金属を含む有機金属錯体などから選ばれた少なくとも一種類が挙げられる。
アルカリ土類金属としては、カルシウム(Ca)(仕事関数:2.9eV)、ストロンチウム(Sr)(仕事関数:2.0eV以上2.5eV以下)、バリウム(Ba)(仕事関数:2.52eV)などが挙げられ、仕事関数が2.9eV以下のアルカリ土類金属が好ましい。
希土類金属としては、スカンジウム(Sc)、イットリウム(Y)、セリウム(Ce)、テルビウム(Tb)、イッテルビウム(Yb)などが挙げられ、仕事関数が2.9eV以下の希土類金属が好ましい。
以上の金属のうち好ましい金属は、特に還元能力が高く、電子注入域への比較的少量の添加により、有機EL素子における発光輝度の向上や長寿命化が可能である。
アルカリ土類金属化合物としては、例えば、酸化バリウム(BaO)、酸化ストロンチウム(SrO)、酸化カルシウム(CaO)などが挙げられる。また、アルカリ土類金属化合物としては、例えば、BaOおよびSrOを混合したストロンチウム酸バリウム(BaxSr1-xO)(0<x<1)、並びにBaO、およびCaOを混合したカルシウム酸バリウム(BaxCa1-xO)(0<x<1)などが挙げられる。アルカリ土類金属化合物としては、BaO、SrO、CaOが好ましい。
希土類金属化合物としては、例えば、フッ化イッテルビウム(YbF3)、フッ化スカンジウム(ScF3)、酸化スカンジウム(ScO3)、酸化イットリウム(Y2O3)、酸化セリウム(Ce2O3)、フッ化ガドリニウム(GdF3)、フッ化テルビウム(TbF3)などが挙げられ、YbF3、ScF3、TbF3が好ましい。
電子供与性ドーパントおよび有機金属錯体の少なくともいずれかを層状に形成する場合は、界面の有機層である発光材料や電子注入材料を層状に形成した後に、電子供与性ドーパントおよび有機金属錯体の少なくともいずれかを単独で抵抗加熱蒸着法により蒸着し、好ましくは層の厚み0.1nm以上15nm以下で形成する。
電子供与性ドーパントおよび有機金属錯体の少なくともいずれかを島状に形成する場合は、界面の有機層である発光材料や電子注入材料を島状に形成した後に、電子供与性ドーパントおよび有機金属錯体の少なくともいずれかを単独で抵抗加熱蒸着法により蒸着し、好ましくは島の厚み0.05nm以上1nm以下で形成する。
また、本発明の有機EL素子における、主成分と電子供与性ドーパントおよび有機金属錯体の少なくともいずれかとの割合としては、モル比で主成分:電子供与性ドーパント,有機金属錯体=5:1から1:5までであると好ましく、2:1から1:2までであるとさらに好ましい。
本実施形態の有機EL素子は、透光性基板上に作製する。透光性基板は有機EL素子を支持する基板であり、400nm~700nmの可視領域の光の透過率が50%以上で平滑な基板が好ましい。具体的には、ガラス板、ポリマー板等が挙げられる。ガラス板としては、例えば、ソーダ石灰ガラス、バリウム・ストロンチウム含有ガラス、鉛ガラス、アルミノケイ酸ガラス、ホウケイ酸ガラス、バリウムホウケイ酸ガラス、石英等を原料として用いてなるガラス板が挙げられる。またポリマー板としては、ポリカーボネート、アクリル、ポリエチレンテレフタレート、ポリエーテルサルファイド、ポリサルフォン等を原料として用いてなるポリマー板を挙げることができる。
有機EL素子の陽極は、正孔を正孔輸送層又は発光層に注入する役割を担い、4.5eV以上の仕事関数を有する材料を用いることが効果的である。陽極材料の具体例としては、酸化インジウム錫合金(ITO)、酸化錫(NESA)、酸化インジウム亜鉛酸化物、金、銀、白金、銅等が挙げられる。陽極はこれらの電極物質を蒸着法やスパッタリング法等の方法で薄膜を形成させることにより作製することができる。発光層からの発光を陽極から取り出す場合、陽極の可視領域の光の透過率を10%より大きくすることが好ましい。また、陽極のシート抵抗は、数百Ω/□(オーム/スクウェア)以下が好ましい。陽極の膜厚は、材料にもよるが、通常10nm~1μm、好ましくは10nm~200nmの範囲で選択される。
陰極は電子注入層、電子輸送層又は発光層に電子を注入する役割を担い、仕事関数の小さい材料により形成するのが好ましい。陰極材料は特に限定されないが、具体的にはインジウム、アルミニウム、マグネシウム、マグネシウム-インジウム合金、マグネシウム-アルミニウム合金、アルミニウム-リチウム合金、アルミニウム-スカンジウム-リチウム合金、マグネシウム-銀合金等が使用できる。陰極も、陽極と同様に、蒸着法やスパッタリング法等の方法で薄膜を形成させることにより作製することができる。また、必要に応じて、陰極側から発光を取り出してもよい。
発光機能を有する有機層であって、ドーピングシステムを採用する場合、ホストとドーパントを含んでいる。このとき、ホストは、主に電子と正孔の再結合を促し、励起子を発光層内に閉じ込める機能を有し、ドーパントは、再結合で得られた励起子を効率的に発光させる機能を有する。
燐光素子の場合、ホストは主にドーパントで生成された励起子を発光層内に閉じ込める機能を有する。
また、量子収率の高いドーパントを二種類以上入れることによって、それぞれのドーパントが発光するダブルドーパントを採用してもよい。具体的には、ホスト、赤色ドーパント及び緑色ドーパントを共蒸着することによって、発光層を共通化して黄色発光を実現する態様が挙げられる。
発光層への正孔の注入し易さと電子の注入し易さは異なっていてもよく、また、発光層中での正孔と電子の移動度で表される正孔輸送能と電子輸送能が異なっていてもよい。
発光層は、分子堆積膜であることが好ましい。分子堆積膜とは、気相状態の材料化合物から沈着され形成された薄膜や、溶液状態又は液相状態の材料化合物から固体化され形成された膜のことである。通常、この分子堆積膜は、LB法により形成された薄膜(分子累積膜)とは、凝集構造の相違や、高次構造の相違、またはそれに起因する機能的な相違により区分することができる。
燐光ドーパントとして好ましい有機金属錯体の具体例を、以下に示す。
R81~R88は、それぞれ独立に、水素原子、置換もしくは無置換の環形成炭素数6~50のアリール基、置換もしくは無置換の環形成原子数5~50の複素環基、置換もしくは無置換の炭素数1~50のアルキル基、置換もしくは無置換の炭素数1~50のアルコキシ基、置換もしくは無置換の炭素数7~50のアラルキル基、置換もしくは無置換の環形成炭素数6~50のアリールオキシ基、置換もしくは無置換の環形成炭素数6~50のアリールチオ基、置換もしくは無置換の炭素数2~50のアルコキシカルボニル基、置換もしくは無置換のシリル基、カルボキシル基、ハロゲン原子、シアノ基、ニトロ基又はヒドロキシル基である。)
上記環形成原子数5~50の複素環基としては、いずれも、環形成原子数5~40の複素環基が好ましく、環形成原子数5~30の複素環基がより好ましい。
上記炭素数1~50のアルキル基としては、炭素数1~30のアルキル基が好ましく、炭素数1~10のアルキル基がより好ましく、炭素数1~5のアルキル基がさらに好ましい。
上記炭素数1~50のアルコキシ基としては、炭素数1~30のアルコキシ基が好ましく、炭素数1~10のアルコキシ基がより好ましく、炭素数1~5のアルコキシ基がさらに好ましい。
上記炭素数7~50のアラルキル基としては、炭素数7~30のアラルキル基が好ましく、炭素数7~20のアラルキル基がより好ましい。
上記環形成炭素数6~50のアリールオキシ基としては、環形成炭素数6~40のアリールオキシ基が好ましく、環形成炭素数6~30のアリールオキシ基がより好ましい。
上記環形成炭素数6~50のアリールチオ基としては、環形成炭素数6~40のアリールチオ基が好ましく、環形成炭素数6~30のアリールチオ基がより好ましい。
上記炭素数2~50のアルコキシカルボニル基としては、炭素数2~30のアルコキシカルボニル基が好ましく、炭素数2~10のアルコキシカルボニル基がより好ましく、炭素数2~5のアルコキシカルボニル基がさらに好ましい。
上記ハロゲン原子としては、フッ素原子、塩素原子、臭素原子等が挙げられる。
Ar31及びAr32は、置換もしくは無置換の環形成炭素数6~50のアリール基であることが好ましい。
R81~R88の好ましい態様も前記同様である。また、R89の好ましい態様も、R81~R88と同様である。aは1~3の整数が好ましく、1又は2がより好ましい。
Ar33が表す環形成炭素数6~50のアリール基としては、環形成炭素数6~40のアリール基が好ましく、環形成炭素数6~30のアリール基がより好ましく、環形成炭素数6~20のアリール基がさらに好ましく、環形成炭素数6~12のアリール基がよりさらに好ましい。
アリールジアミン誘導体としては、より具体的には、下記式(11)で表されるアリールジアミン誘導体が好ましい。
L21は、置換もしくは無置換の環形成炭素数6~50のアリーレン基又は置換もしくは無置換の環形成原子数5~50のヘテロアリーレン基を表す。)
上記環形成原子数5~50のヘテロアリール基としては、環形成原子数5~40のヘテロアリール基が好ましく、環形成原子数5~30のヘテロアリール基がより好ましく、環形成原子数5~20のヘテロアリール基がさらに好ましい。ヘテロアリール基としては、カルバゾリル基、ジベンゾフラニル基、ジベンゾチオフェニル基などが挙げられ、ジベンゾフラニル基が好ましい。該ヘテロアリール基の好ましい置換基としては、環形成炭素数6~30(好ましくは6~20、より好ましくは6~12)のアリール基が挙げられ、フェニル基、ナフチル基がより好ましい。
上記環形成炭素数6~50のアリーレン基としては、環形成炭素数6~40のアリーレン基が好ましく、環形成炭素数6~30のアリーレン基がより好ましく、環形成炭素数6~20のアリーレン基がさらに好ましく、ピレニル基がよりさらに好ましい。
正孔輸送層は、発光層と陽極との間に形成される有機層であって、正孔を陽極から発光層へ輸送する機能を有する。正孔輸送層が複数層で構成される場合、陽極に近い有機層を正孔注入層と定義することがある。正孔注入層は、陽極から正孔を効率的に有機層に注入する機能を有する。
また、前記式(H)において、Lは置換もしくは無置換の環形成炭素数6~50の芳香族炭化水素基又は縮合芳香族炭化水素基、又は置換もしくは無置換の環形成原子数5~50の芳香族複素環基又は縮合芳香族複素環基を表す。
正孔輸送層の膜厚は特に限定されないが、10~200nmであるのが好ましい。
前記アクセプター材料としては下記式(K)で表される化合物が好ましい。
R27としては、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。
アクセプター材料を含有する層の膜厚は特に限定されないが、5~20nmであるのが好ましい。
上述の正孔輸送層や電子輸送帯域においては、特許第3695714号明細書に記載されているように、ドナー性材料のドーピング(n)やアクセプター性材料のドーピング(p)により、キャリア注入能を調整することができる。
nドーピングの代表例としては、電子輸送材料にLiやCs等の金属をドーピングする方法が挙げられ、pドーピングの代表例としては、正孔輸送材料にF4TCNQ(2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane)等のアクセプター材料をドーピングする方法が挙げられる。
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、電子輸送性と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。スペース層には、上述の正孔輸送層に用いられる材料と同様の材料が用いられる。
本実施形態の有機EL素子は、発光層に隣接する部分に、電子障壁層、正孔障壁層、トリプレット障壁層といった障壁層を有することが好ましい。ここで、電子障壁層とは、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、正孔障壁層とは、発光層から電子輸送層へ正孔が漏れることを防ぐ層である。
トリプレット障壁層は、発光層で生成する三重項励起子が、周辺の層へ拡散することを防止し、三重項励起子を発光層内に閉じ込めることによって三重項励起子の発光ドーパント以外の電子輸送層の分子上でのエネルギー失活を抑制する機能を有する。
電子注入層は、電界強度0.04~0.5MV/cmの範囲において、10-6cm2/(V・s)以上であることが望ましい。これにより陰極からの電子輸送層への電子注入が促進され、ひいては隣接する障壁層、発光層への電子注入も促進し、より低電圧での駆動を可能にするためである。
本実施形態の有機EL素子の各層の形成方法としては、上記で特に言及した以外には制限されないが、真空蒸着法、スパッタリング法、プラズマ法、イオンプレーティング法などの乾式成膜法や、スピンコーティング法、ディッピング法、フローコーティング法、インクジェット法などの湿式成膜法などの公知の方法を採用することができる。
本実施形態の有機EL素子の各有機層の膜厚は、上記で特に言及した以外には制限されないが、一般に膜厚が薄すぎるとピンホール等の欠陥が生じやすく、逆に厚すぎると高い印加電圧が必要となり効率が悪くなるため、通常は数nmから1μmの範囲が好ましい。
本実施形態に係る有機EL素子は、有機ELパネルモジュール等の表示部品、テレビ、携帯電話、タブレットもしくはパーソナルコンピュータ等の表示装置、および照明、もしくは車両用灯具の発光装置等の電子機器に使用できる。
なお、本発明は、上述の実施形態に限定されず、本発明の目的を達成できる範囲での変更、改良などは、本発明に含まれる。
化合物(1)の合成スキームを以下に示す。
アルゴン雰囲気下、4-(ピリジン-2-イル)ベンズアルデヒド(5.00 g, 27.3 mmol)、4-ブロモアセトフェノン(5.43 g, 27.3 mmol)、およびナトリウムメトキシド(147 mg, 0.273 mmol)にエタノール(88 mL)を加え、室温で2時間撹拌し、さらに還流温度で3時間撹拌した。その後、ベンズアミジン塩酸塩(4.40 g, 28.1 mmol)、および水酸化ナトリウム(2.18 g, 54.6 mmol)を添加して、還流温度で3時間撹拌した。反応終了後、析出物をろ別し、水とメタノールで洗浄し、中間体(A1)(5.13 g, 11.0 mmol)(収率40%)を得た。
アルゴン雰囲気下、中間体(A1)(2.97 g, 6.40 mmol)、カルバゾール(1.07 g, 6.40 mmol)、トリス(ジベンジリデンアセトン)ジパラジウム(0)(117 mg, 0.128 mmol)、tert-ブチルホスフィンのテトラフルオロホウ酸塩(149 mg, 0.514 mmol)、およびナトリウム-tert-ブトキシド(861 mg, 8.96 mmol)にトルエン(26 mL)を加え、還流温度で7時間撹拌した。反応終了後、混合物をろ別し、水とメタノールで洗浄した。混合物を還流温度のトルエンに溶解し、シリカゲルのショートカラムクロマトグラフィーに通した。その後、溶液をトルエンの還流温度まで加熱し、100℃でメタノールを加えた後、析出した固体をろ別乾燥して化合物(1)(2.34 g, 4.25 mmol)(収率66%)を得た。本化合物は、質量分析の結果、目的物であり、分子量550.65に対し、m/e=550であった。
化合物(2)の合成スキームを以下に示す。
化合物(3)の合成スキームを以下に示す。
化合物(4)の合成スキームを以下に示す。
化合物(5)の合成スキームを以下に示す。
以下に、有機EL素子の製造に用いた化合物を示す。
25mm×75mm×1.1mm厚のITO透明電極(陽極)付きガラス基板(ジオマティック社製)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分間行なった。洗浄後の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上記化合物(HI-1)を蒸着して膜厚10nmのHI-1膜を成膜し、正孔注入層を形成した。
次に、この正孔注入層上に、第1正孔輸送材料として上記化合物(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、この第1正孔輸送層上に、上記化合物(HT-2)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。
さらに、このHT-2膜上に膜厚25nmで、ホスト材料として上記化合物(BH-1)と、ドーパント材料として上記化合物(BD-1)とを24:1の重量比で共蒸着により成膜し、発光層とした。
さらに、上記合成例1にて合成した化合物(1)を蒸着し、膜厚10nmの電子注入層を形成した。
その後、LiFを膜厚1nmで成膜し、このLiF膜上に金属Alを150nm蒸着させ金属陰極を形成することにより、有機EL素子を製造した。
実施例1において、化合物(1)の代わりに表1に示す化合物を用いた以外は同様にして有機EL素子を作製し、評価した。
実施例1~3及び比較例1において作製した有機EL素子について、以下の評価を行った。評価結果を表1に示す。
電流密度が10mA/cm2となるように陽極(ITO透明電極)と金属陰極(金属Al)との間に通電したときの電圧(単位:V)を計測した。
・外部量子効率EQE
電流密度が10mA/cm2となるように素子に電圧を印加した時の分光放射輝度スペクトルを分光放射輝度計CS-1000(コニカミノルタ社製)で計測した。得られた上記分光放射輝度スペクトルから、ランバシアン放射を行なったと仮定し外部量子効率(単位:%)を算出した。
これは本発明の一実施形態に係る化合物である化合物(1)~(3)が、前記一般式(1)においてAzで表される末端の含窒素複素環基により電子注入性が向上するためである。このように、比較例1の化合物E-1の末端のフェニル基を含窒素複素環基に置換するだけで、電子輸送材料として大きく性能改善することが分かる。すなわち、化合物(E-1)を用いた場合と比べて、化合物(1)~(3)を用いたことで、駆動電圧および発光効率の点で、有機EL素子の性能が向上したことが分かる。
25mm×75mm×1.1mm厚のITO透明電極(陽極)付きガラス基板(ジオマティック社製)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分間行なった。洗浄後の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上記化合物(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、この正孔注入層上に、第1正孔輸送材料として上記化合物(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、この第1正孔輸送層上に、上記化合物(HT-2)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。
さらに、このHT-2膜上に膜厚25nmで、ホスト材料として下記化合物(BH-2)と、ドーパント材料として下記化合物(BD-2)とを24:1の重量比で共蒸着により成膜し、発光層とした。
この発光層上に上記合成例4で合成した化合物(4)を蒸着して、膜厚25nmの化合物(4)膜を成膜し、電子輸送層を形成した。
その後、LiFを膜厚1nmで成膜し、このLiF膜上に金属Alを80nm蒸着させ金属陰極を形成することにより、有機EL素子を製造した。
実施例5の有機EL素子は、実施例4における化合物(4)の代わりに上記合成例5で合成した化合物(5)を用いたこと以外は実施例4と同様にして製造した。
比較例2の有機EL素子は、実施例4における化合物(4)の代わりに下記化合物(E-2)を用いたこと以外は実施例4と同様にして製造した。
25mm×75mm×1.1mm厚のITO透明電極(陽極)付きガラス基板(ジオマティック社製)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分間行なった。洗浄後の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、この正孔注入層上に、第1正孔輸送材料として前記化合物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、この第1正孔輸送層上に、前記化合物HT-2を蒸着して膜厚10nmのHT-2膜を成膜し、第4正孔輸送層を形成した。
さらに、このHT-2膜上に膜厚25nmで前記ホストBH-2と前記ドーパントBD-2を24:1の質量比で共蒸着により成膜し、発光層とした。
この発光層成膜に続けて、前記合成例2で合成した化合物(2)と8-キノリノラトリチウム(Liq)とを50:50の質量比で共蒸着により成膜し、膜厚25mの電子輸送層を成膜した。この電子輸送層上に金属Alを蒸着させ、金属陰極を膜厚80nmで形成し有機EL素子を製造した。
比較例3の有機EL素子は、実施例6における化合物(2)の代わりに下記化合物(E-3)を用いたこと以外は実施例6と同様にして製造した。
Claims (20)
- 下記一般式(1)で表されることを特徴とする化合物。
(前記一般式(1)において、
R3は、それぞれ独立に、
水素原子、
ハロゲン原子、
ヒドロキシル基、
シアノ基、
置換もしくは無置換の炭素数1~30のアルキル基、
置換もしくは無置換の炭素数3~30のアルキルシリル基、
置換もしくは無置換の環形成炭素数6~60のアリールシリル基、
置換もしくは無置換の炭素数1~30のアルコキシ基、
置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、
置換もしくは無置換の炭素数2~30のアルキルアミノ基、
置換もしくは無置換の環形成炭素数6~60のアリールアミノ基、
置換もしくは無置換の炭素数1~30のアルキルチオ基、
置換もしくは無置換の環形成炭素数6~30のアリールチオ基、
置換もしくは無置換の環形成炭素数6~30の芳香族炭化水素基、又は
置換もしくは無置換の環形成原子数5~30の複素環基である。
R2は、置換もしくは無置換の環形成炭素数6~30の芳香族炭化水素基である。
R2が置換基を有する場合、置換基は、
ハロゲン原子、
ヒドロキシル基、
シアノ基、
ニトロ基、
カルボキシ基、
置換もしくは無置換の炭素数1~30のアルキル基、
置換もしくは無置換の炭素数2~30のアルケニル基、
置換もしくは無置換の炭素数2~30のアルキニル基、
置換もしくは無置換の炭素数3~30のアルキルシリル基、
置換もしくは無置換の環形成炭素数6~60のアリールシリル基、
置換もしくは無置換の炭素数1~30のアルコキシ基、
置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、
置換もしくは無置換の環形成炭素数6~30のアリールチオ基、
置換もしくは無置換の環形成炭素数5~30の含酸素複素環基、
置換もしくは無置換の環形成炭素数5~30の含硫黄複素環基、又は
置換もしくは無置換の環形成炭素数6~30の芳香族炭化水素基である。
前記アリールオキシ基および前記アリールチオ基が置換基を有する場合、隣接する置換基が結合して環を形成する場合と環を形成しない場合とがある。
L1は、単結合または連結基であり、L1における連結基としては、
アルケニレン基、
アルキニレン基、
置換もしくは無置換の環形成炭素数6~30の芳香族炭化水素基、
置換もしくは無置換の環形成原子数5~30の複素環基、
前記芳香族炭化水素基から選ばれる2個から4個の基が結合してなる多重連結基、
前記複素環基から選ばれる2個から4個の基が結合してなる多重連結基、又は
前記芳香族炭化水素基及び前記複素環基から選ばれる2個から4個の基が結合してなる多重連結基である。
なお、前記多重連結基を構成する前記芳香族炭化水素基および前記複素環基は、互いに同一または異なり、隣り合う基が結合してさらに環を形成する場合と、環を形成しない場合とがある。
L2は、連結基であり、連結基としては、L1における連結基と同義である。
nおよびmは、それぞれ独立に1以上5以下の整数である。
nが2以上5以下の整数である場合、複数のCzは、互いに同一であるか、または異なる。
mが2以上5以下の整数である場合、Azは、互いに同一であるか、または異なる。
Czは、下記一般式(1a)で表され、
Azは、下記一般式(11)で表される。)
(前記一般式(1a)において、
X1~X8は、それぞれ独立にCRまたは窒素原子である。
RおよびR1は、それぞれ独立に、
水素原子、
ハロゲン原子、
ヒドロキシル基、
シアノ基、
置換もしくは無置換の炭素数1~30のアルキル基、
置換もしくは無置換の炭素数3~30のアルキルシリル基、
置換もしくは無置換の環形成炭素数6~60のアリールシリル基、
置換もしくは無置換の炭素数1~30のアルコキシ基、
置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、
置換もしくは無置換の炭素数2~30のアルキルアミノ基、
置換もしくは無置換の環形成炭素数6~60のアリールアミノ基、
置換もしくは無置換の炭素数1~30のアルキルチオ基、
置換もしくは無置換の環形成炭素数6~30のアリールチオ基、
置換もしくは無置換の環形成炭素数6~30の芳香族炭化水素基、又は
置換もしくは無置換の環形成原子数5~30の複素環基である。
互いに隣接するRが結合して、環を形成する場合と、環を形成しない場合とがある。
Rが複数ある場合、複数のRは、互いに同一、または異なる。
ただし、RおよびR1のいずれか1つは、前記一般式(1)のL1に結合する単結合である。
また、R1と隣接するRとが互いに結合して、環を形成する場合と、環を形成しない場合とがある。)
(前記一般式(11)において、
X9は、CR9または窒素原子であり、X10は、CR10または窒素原子である。
R4~R6,R9およびR10は、それぞれ独立に、
水素原子、
ハロゲン原子、
ヒドロキシル基、
シアノ基、
置換もしくは無置換の炭素数1~30のアルキル基、
置換もしくは無置換の炭素数3~30のアルキルシリル基、
置換もしくは無置換の環形成炭素数6~60のアリールシリル基、
置換もしくは無置換の炭素数1~30のアルコキシ基、
置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、
置換もしくは無置換の炭素数2~30のアルキルアミノ基、
置換もしくは無置換の環形成炭素数6~60のアリールアミノ基、
置換もしくは無置換の炭素数1~30のアルキルチオ基、又は
置換もしくは無置換の環形成炭素数6~30のアリールチオ基である。
R4~R6,R9およびR10のうち隣り合う基が結合してさらに環を形成する場合と、環を形成しない場合とがある。
ただし、R4~R6,R9およびR10のうちいずれか1つは、L2に結合する単結合である。) - 請求項1に記載の化合物であって、前記一般式(1)は、下記一般式(1A)または(1B)で表されることを特徴とする化合物。
(前記一般式(1A)においてL1,L2,R2,R3,Az,n,mは、それぞれ前記一般式(1)におけるL1,L2,R2,R3,Az,n,mと同義である。
X1~X8は、それぞれ前記一般式(1a)におけるX1~X8と同義である。)
(前記一般式(1B)において、
L1,L2,R2,R3,Az,n,mは、それぞれ前記一般式(1)におけるL1,L2,R2,R3,Az,n,mと同義である。
R1,X1~X8は、それぞれ前記一般式(1a)におけるR1,X1~X8と同義である。
ただし、前記一般式(1B)において、X1~X8のうちいずれか1つは、L1に結合する炭素原子である。) - 請求項1または請求項2に記載の化合物において、
前記X1からX8までは、それぞれ独立にCRであることを特徴とする化合物。 - 請求項1から請求項3のいずれか一項に記載の化合物において、
前記Azは、置換もしくは無置換のピリジン環、置換もしくは無置換のピリミジン環、置換もしくは無置換のトリアジン環、置換もしくは無置換のキノリン環、置換もしくは無置換のイソキノリン環、置換もしくは無置換のキナゾリン環、および置換もしくは無置換のフェナントロリン環のいずれかから選ばれることを特徴とする化合物。 - 請求項4に記載の化合物において、
前記Azは、無置換のピリジン環、無置換のピリミジン環、無置換のトリアジン環、無置換のキノリン環、無置換のイソキノリン環、無置換のキナゾリン環および無置換のフェナントロリン環のいずれかから選ばれることを特徴とする化合物。 - 請求項1から請求項4のいずれか一項に記載の化合物において、
前記X9は、CR9であり、前記X10は、CR10であることを特徴とする化合物。 - 請求項2から請求項6のいずれか一項に記載の化合物において、
前記一般式(1A)で表されることを特徴とする化合物。 - 請求項1から請求項7までのいずれか一項に記載の化合物において、
前記L1は、置換または無置換の環形成炭素数6~30の芳香族炭化水素基であることを特徴とする化合物。 - 請求項1から請求項8のいずれか一項に記載の化合物において、
前記L1は、置換または無置換のベンゼン環であることを特徴とする化合物。 - 請求項1から請求項9のいずれか一項に記載の化合物において、
前記nは、1または2であり、
前記mは、1であることを特徴とする化合物。 - 請求項1から請求項12のいずれか一項に記載の化合物において、
前記L2は、置換もしくは無置換の環形成炭素数6~30の芳香族炭化水素基であることを特徴とする化合物。 - 請求項1から請求項13のいずれか一項に記載の化合物において、
前記L2は、置換または無置換のベンゼン環であることを特徴とする化合物。 - 請求項1から請求項14のいずれか一項に記載の化合物を含むことを特徴とする有機エレクトロルミネッセンス素子用材料。
- 陽極と、
前記陽極と対向して設けられた陰極と、
前記陽極および前記陰極の間に、少なくとも発光層を含む1層以上の有機層と、を有し、
前記有機層の少なくとも1層が、請求項1から請求項14のいずれか一項に記載の化合物を含むことを特徴とする有機エレクトロルミネッセンス素子。 - 請求項16に記載の有機エレクトロルミネッセンス素子において、
前記有機層は、前記発光層と前記陰極との間に電子輸送帯域を含み、
前記化合物を含む前記有機層の少なくとも1層は、前記電子輸送帯域であることを特徴とする有機エレクトロルミネッセンス素子。 - 請求項17に記載の有機エレクトロルミネッセンス素子において、
前記電子輸送帯域が、電子供与性ドーパントおよび有機金属錯体の少なくとも一方をさらに含有することを特徴とする有機エレクトロルミネッセンス素子。 - 請求項18に記載の有機エレクトロルミネッセンス素子において、
前記電子供与性ドーパントおよび有機金属錯体の少なくとも一方が、アルカリ金属、アルカリ金属化合物、アルカリ土類金属、アルカリ土類金属化合物、希土類金属、希土類金属化合物、アルカリ金属を含む有機金属錯体、アルカリ土類金属を含む有機金属錯体、および希土類金属を含む有機金属錯体からなる群から選択される少なくとも1種であることを特徴とする有機エレクトロルミネッセンス素子。 - 請求項16から請求項19のいずれか一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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KR101882592B1 (ko) | 2018-08-24 |
JP6182217B2 (ja) | 2017-08-16 |
CN105473569B (zh) | 2021-01-01 |
EP3040335B1 (en) | 2019-04-03 |
CN105473569A (zh) | 2016-04-06 |
JPWO2015072520A1 (ja) | 2017-03-16 |
KR20160075492A (ko) | 2016-06-29 |
EP3040335A4 (en) | 2017-03-22 |
US10217954B2 (en) | 2019-02-26 |
EP3040335A1 (en) | 2016-07-06 |
US20160181564A1 (en) | 2016-06-23 |
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