WO2014157574A1 - 縮合フルオランテン化合物、これを用いた有機エレクトロルミネッセンス素子用材料、並びにこれを用いた有機エレクトロルミネッセンス素子及び電子機器 - Google Patents
縮合フルオランテン化合物、これを用いた有機エレクトロルミネッセンス素子用材料、並びにこれを用いた有機エレクトロルミネッセンス素子及び電子機器 Download PDFInfo
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- WO2014157574A1 WO2014157574A1 PCT/JP2014/059009 JP2014059009W WO2014157574A1 WO 2014157574 A1 WO2014157574 A1 WO 2014157574A1 JP 2014059009 W JP2014059009 W JP 2014059009W WO 2014157574 A1 WO2014157574 A1 WO 2014157574A1
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- -1 fluoranthene compound Chemical class 0.000 title claims abstract description 132
- 239000000463 material Substances 0.000 title claims abstract description 125
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 150000001875 compounds Chemical class 0.000 title abstract description 76
- 125000004432 carbon atom Chemical group C* 0.000 claims description 239
- 125000001424 substituent group Chemical group 0.000 claims description 95
- 238000005401 electroluminescence Methods 0.000 claims description 80
- 125000006413 ring segment Chemical group 0.000 claims description 51
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 47
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 42
- 125000004429 atom Chemical group 0.000 claims description 29
- 239000010409 thin film Substances 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 24
- 229920006395 saturated elastomer Polymers 0.000 claims description 24
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 125000004434 sulfur atom Chemical group 0.000 claims description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 229910052741 iridium Inorganic materials 0.000 claims description 4
- 125000005647 linker group Chemical group 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 abstract description 13
- 125000005842 heteroatom Chemical group 0.000 abstract description 3
- 239000010410 layer Substances 0.000 description 296
- 125000003118 aryl group Chemical group 0.000 description 86
- 230000015572 biosynthetic process Effects 0.000 description 63
- 238000003786 synthesis reaction Methods 0.000 description 58
- 125000000217 alkyl group Chemical group 0.000 description 51
- 239000000047 product Substances 0.000 description 49
- 230000005525 hole transport Effects 0.000 description 46
- 239000002019 doping agent Substances 0.000 description 45
- 238000001819 mass spectrum Methods 0.000 description 45
- 125000001072 heteroaryl group Chemical group 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 229910052799 carbon Inorganic materials 0.000 description 27
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 26
- 238000002347 injection Methods 0.000 description 26
- 239000007924 injection Substances 0.000 description 26
- 229940125904 compound 1 Drugs 0.000 description 25
- 230000004888 barrier function Effects 0.000 description 22
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 20
- 125000003545 alkoxy group Chemical group 0.000 description 20
- 239000010408 film Substances 0.000 description 18
- 125000000732 arylene group Chemical group 0.000 description 17
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 15
- 229940125782 compound 2 Drugs 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 125000004104 aryloxy group Chemical group 0.000 description 13
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 13
- 125000003277 amino group Chemical group 0.000 description 12
- 125000003710 aryl alkyl group Chemical group 0.000 description 12
- 229910052805 deuterium Inorganic materials 0.000 description 12
- 125000005843 halogen group Chemical group 0.000 description 12
- 125000001624 naphthyl group Chemical group 0.000 description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 150000001975 deuterium Chemical group 0.000 description 10
- 125000005549 heteroarylene group Chemical group 0.000 description 10
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 150000001454 anthracenes Chemical class 0.000 description 8
- 150000001721 carbon Chemical class 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- 125000001188 haloalkyl group Chemical group 0.000 description 8
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 7
- 239000012300 argon atmosphere Substances 0.000 description 7
- 150000004982 aromatic amines Chemical class 0.000 description 7
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
- ZUXKRUWSXHOCPI-UHFFFAOYSA-N 2-bromo-3-nitrofluoranthene Chemical compound BrC1=CC=2C3=CC=CC=C3C3=CC=CC(=C1[N+](=O)[O-])C23 ZUXKRUWSXHOCPI-UHFFFAOYSA-N 0.000 description 6
- GEDOYYDMCZUHNW-UHFFFAOYSA-N 2-bromotriphenylene Chemical group C1=CC=C2C3=CC(Br)=CC=C3C3=CC=CC=C3C2=C1 GEDOYYDMCZUHNW-UHFFFAOYSA-N 0.000 description 6
- FFTQZFWZHRWKRI-UHFFFAOYSA-N 2-naphthalen-1-yl-3-nitrofluoranthene Chemical compound C1(=CC=CC2=CC=CC=C12)C1=CC=2C3=CC=CC=C3C3=CC=CC(=C1[N+](=O)[O-])C23 FFTQZFWZHRWKRI-UHFFFAOYSA-N 0.000 description 6
- MNJMBVHRXXIFSX-UHFFFAOYSA-N 3-(3-bromophenyl)fluoranthene Chemical compound BrC1=CC=CC(C=2C=3C=CC=C4C5=CC=CC=C5C(C=34)=CC=2)=C1 MNJMBVHRXXIFSX-UHFFFAOYSA-N 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- 125000001041 indolyl group Chemical group 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 125000003373 pyrazinyl group Chemical group 0.000 description 6
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 6
- 238000005215 recombination Methods 0.000 description 6
- 230000006798 recombination Effects 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- JZOIZKBKSZMVRV-UHFFFAOYSA-N benzo(a)triphenylene Chemical group C1=CC=CC2=C3C4=CC=CC=C4C=CC3=C(C=CC=C3)C3=C21 JZOIZKBKSZMVRV-UHFFFAOYSA-N 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 229940125758 compound 15 Drugs 0.000 description 5
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 238000001296 phosphorescence spectrum Methods 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 229910052761 rare earth metal Inorganic materials 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 125000005110 aryl thio group Chemical group 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 229910052792 caesium Inorganic materials 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000012212 insulator Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000005956 isoquinolyl group Chemical group 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 4
- 229960003540 oxyquinoline Drugs 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 125000005561 phenanthryl group Chemical group 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000005581 pyrene group Chemical group 0.000 description 4
- 125000001725 pyrenyl group Chemical group 0.000 description 4
- 125000005493 quinolyl group Chemical group 0.000 description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 4
- 150000002910 rare earth metals Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 230000027756 respiratory electron transport chain Effects 0.000 description 4
- 230000000630 rising effect Effects 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 125000003808 silyl group Chemical class [H][Si]([H])([H])[*] 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- 125000004306 triazinyl group Chemical group 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 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
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 3
- WCXFCLXZMIFHBU-UHFFFAOYSA-N 3-bromofluoranthene Chemical compound C12=CC=CC=C2C2=CC=CC3=C2C1=CC=C3Br WCXFCLXZMIFHBU-UHFFFAOYSA-N 0.000 description 3
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical group C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229910018068 Li 2 O Inorganic materials 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- DRGJXDFDGMPVQA-UHFFFAOYSA-N N-(2-chlorophenyl)fluoranthen-3-amine Chemical compound ClC1=C(NC=2C=CC=3C4=CC=CC=C4C4=CC=CC2C34)C=CC=C1 DRGJXDFDGMPVQA-UHFFFAOYSA-N 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 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
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 3
- 229940125773 compound 10 Drugs 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
- XNKVIGSNRYAOQZ-UHFFFAOYSA-N dibenzofluorene Chemical group C12=CC=CC=C2C2=CC=CC=C2C2=C1CC1=CC=CC=C12 XNKVIGSNRYAOQZ-UHFFFAOYSA-N 0.000 description 3
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 3
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 3
- 230000005281 excited state Effects 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
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- 150000002484 inorganic compounds Chemical class 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004957 naphthylene group Chemical group 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000004866 oxadiazoles Chemical class 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 3
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- 238000006862 quantum yield reaction Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 238000002366 time-of-flight method Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005106 triarylsilyl group Chemical group 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052727 yttrium Inorganic materials 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 condensed fluoranthene compound, a material for an organic electroluminescence element using the same, and an organic electroluminescence element and electronic equipment using the same.
- an organic electroluminescence (EL) element is composed of an anode, a cathode, and one or more organic thin film layers sandwiched between the anode and the cathode.
- a voltage is applied between both electrodes, electrons from the cathode side and holes from the anode side are injected into the light emitting region, and the injected electrons and holes recombine in the light emitting region to generate an excited state, which is excited.
- Light is emitted when the state returns to the ground state.
- organic EL elements can be obtained in various light emitting colors by using various light emitting materials for the light emitting layer, and therefore, researches for practical application to displays and the like are active. In particular, research on light emitting materials of the three primary colors of red, green, and blue is the most active, and intensive research has been conducted with the aim of improving characteristics.
- Patent Documents 1 to 3 disclose compounds in which an indole structure is condensed at a specific position on a fluoranthene ring.
- development of new material systems is required in order to further improve device performance.
- the present invention has been made to solve the above-described problems, and an object thereof is to provide a novel material useful as an organic EL element material.
- Patent Documents 1 to 3 are only specific compounds having an indolo (f) fluoranthene skeleton or an indolo [2,3-b] fluoranthene skeleton.
- f indolo
- 2,3-b indolo [2,3-b] fluoranthene skeleton
- X a represents Si (R 13a ) (R 14a ), N (R 15a ), a sulfur atom, or an oxygen atom.
- R 1a to R 15a each independently represents a hydrogen atom or a substituent, and adjacent substituents of R 1a to R 15a may be bonded to each other to form a saturated or unsaturated ring structure.
- [2] A material for an organic electroluminescence device containing the condensed fluoranthene compound according to [1].
- the present invention provides a novel material useful as an organic EL element material and an organic EL element using the same.
- the “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. The carbon number of the substituent in the case where it is present 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. In this case, the number of substituent atoms is not included.
- YY is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
- unsubstituted ZZ group in the case of “substituted or unsubstituted ZZ group” means that the hydrogen atom of the ZZ group is not substituted with a substituent.
- hydroxogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (protium), deuterium (deuterium), and tritium (tritium).
- the “ring-forming carbon number” means the ring itself of a compound having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound). This represents the number of carbon atoms among the constituent atoms.
- the carbon contained in the substituent is not included in the ring-forming carbon.
- the “ring-forming carbon number” described below is the same unless otherwise specified.
- 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 ring-forming carbon number.
- the “number of ring-forming atoms” means a compound (for example, a monocyclic compound, a condensed ring compound, a bridging compound, or a carbocyclic compound) having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic ring, a condensed ring, or a ring assembly).
- a heterocyclic compound represents the number of atoms constituting the ring itself.
- An atom that does not constitute a ring for example, a hydrogen atom that terminates a bond of an atom that constitutes a ring
- an atom contained in a substituent when the ring is substituted by a substituent is not included in the number of ring-forming atoms.
- the “number of ring-forming atoms” described below is the same unless otherwise specified.
- the pyridine ring has 6 ring atoms
- the quinazoline ring has 10 ring atoms
- the furan ring has 5 ring atoms.
- the hydrogen atoms bonded to the ring-forming carbon atoms of the pyridine ring and quinazoline ring and the atoms constituting the substituent are not included in the number of ring-forming atoms. 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.
- an optional substituent when referred to as “substituted or unsubstituted” is an alkyl group having 1 to 50 carbon atoms (preferably 1 to 18 and more preferably 1 to 8); 3 to 50 ring carbon atoms (preferably A cycloalkyl group having 3 to 10, more preferably 3 to 8, and further preferably 5 or 6; an aryl group having 6 to 50 ring carbon atoms (preferably 6 to 25, more preferably 6 to 18); ring formation An aralkyl group having 7 to 51 (preferably 7 to 30, more preferably 7 to 20) carbon atoms having an aryl group having 6 to 50 carbon atoms (preferably 6 to 25, more preferably 6 to 18); an amino group; It is selected from an alkyl group having 1 to 50 carbon atoms (preferably 1 to 18, more preferably 1 to 8) and an aryl group having 6 to 50 ring carbon atoms (preferably 6 to 25, more preferably 6 to 18).
- the condensed fluoranthene compound of the present invention is represented by the following general formula (a).
- X a represents Si (R 13a ) (R 14a ), N (R 15a ), a sulfur atom, or an oxygen atom.
- R 1a to R 15a each independently represents a hydrogen atom or a substituent, and adjacent substituents of R 1a to R 15a may be bonded to each other to form a saturated or unsaturated ring structure. . ]
- a polymer having a repeating unit represented by the following general formula (b) and a polymer having a repeating unit represented by the following general formula (d) are also preferred.
- X b represents Si (R 13b ) (R 14b ), N (R 15b ), a sulfur atom, or an oxygen atom.
- R 1b to R 15b each independently represents a hydrogen atom, a substituent, or a bond to L b, and adjacent substituents of R 1b to R 15b are bonded to each other to be saturated or unsaturated.
- a ring structure may be formed.
- L b represents a single bond or a divalent linking group.
- divalent linking group represented by L b include a substituted or unsubstituted aromatic heterocyclic group having 6 to 60 ring carbon atoms (arylene group), a substituted or unsubstituted ring forming atom number of 3 And a heterocyclic group having 1 to 60 carbon atoms (heteroarylene group) and a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms.
- X d represents Si (R 13d ) (R 14d ), N (R 15d ), a sulfur atom, or an oxygen atom.
- R 1d to R 15d each independently represents a hydrogen atom, a substituent, or a bond to L d, and adjacent substituents of R 1d to R 15d are bonded to each other to be saturated or unsaturated.
- a ring structure may be formed.
- L d represents a trivalent organic group.
- condensed fluoranthene compound a compound represented by the following general formula (c) is more preferable.
- X c represents Si (R 13c ) (R 14c ), N (R 15c ), a sulfur atom, or an oxygen atom.
- R 1c to R 15c each independently represents a hydrogen atom, a substituent or a bond to L c, and adjacent substituents among R 1c to R 15c are bonded to each other to form a saturated or unsaturated ring.
- a structure may be formed.
- Y c represents a substituted or unsubstituted p-valent aromatic hydrocarbon group having 6 to 60 ring carbon atoms or a substituted or unsubstituted p-valent heterocyclic group having 3 to 60 ring atoms.
- L c is a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 ring carbon atoms (arylene group), a substituted or unsubstituted divalent complex having 3 to 60 ring atoms.
- p represents an integer of 1 to 6, preferably 1 to 3, more preferably 1 or 2.
- the substituents represented by 1c to R 15c and the substituents represented by R 1d to R 15d are preferably each independently selected from the following group (A): Those selected from the following group (B) are more preferable, those selected from the following group (C) are more preferable, and those selected from the following group (D) are particularly preferable.
- the group (A) is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted ring carbon number 6 to 50 aryl groups, substituted or unsubstituted aralkyl groups having 7 to 51 carbon atoms, amino groups, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, and substituted or unsubstituted aryl groups having 6 to 50 ring carbon atoms A mono- or di-substituted amino group having a substituent selected from the group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, substituted or unsubstituted A mono-, di- or tri-substituted alky
- substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, halogen atom, cyano group, nitro group, substituted or unsubstituted carbon number
- a disubstituted phosphoryl group having a substituent selected from an aryl group having 6 to 50 ring carbon atoms, an alkylsulfonyloxy group, an arylsulfonyloxy group, an alkylcarbonyloxy group, an arylcarbonyloxy group, a boron-containing group,
- the group (B) is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted ring group having 6 to 6 carbon atoms.
- aryl groups substituted or unsubstituted aralkyl groups having 7 to 51 carbon atoms, amino groups, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, and substituted or unsubstituted aryl groups having 6 to 50 ring carbon atoms
- the group (C) is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted ring carbon number 6 to 50 aryl groups, substituted or unsubstituted aralkyl groups having 7 to 51 carbon atoms, amino groups, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, and substituted or unsubstituted aryl groups having 6 to 50 ring carbon atoms A mono- or di-substituted amino group having a substituent selected from the group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, substituted or unsubstituted A mono-, di- or tri-substituted alky
- a substituted or unsubstituted ring atoms 5-50 heteroaryl group a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a halogen atom, a cyano group, and a group consisting of nitro group.
- the group (D) is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted ring carbon number 6 to A mono- or di-substituted amino group having a substituent selected from a 50 aryl group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted Alternatively, it is a group consisting of an unsubstituted heteroaryl group having 5 to 50 ring atoms, a halogen atom, and a cyano group.
- alkyl group having 1 to 50 carbon atoms examples include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, and n-butyl group.
- Examples of the cycloalkyl group having 3 to 50 ring carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclo A heptyl group, a cyclooctyl group, an adamantyl group etc. are mentioned, A cyclopentyl group and a cyclohexyl group are preferable.
- Examples of the aryl group having 6 to 50 ring carbon atoms include, for example, a phenyl group, a naphthyl group, a naphthylphenyl group, and a biphenylyl group.
- Terphenylyl group acenaphthylenyl group, anthryl group, benzoanthryl group, aceanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, fluorenyl group, 9,9'-spirobifluorenyl group, benzofluorenyl Group, dibenzofluorenyl group, picenyl group, pentaphenyl group, pentacenyl group, pyrenyl group, chrycenyl group, benzocricenyl group, s-indacenyl group, as-indacenyl group, fluoranthenyl group, benzofluoranthenyl group, tetracenyl group , Triphenylenyl group, benzotriphenylenyl group Perylenyl group, coronyl group, dibenzoanthryl group, etc., phenyl group, naphthyl group
- the arylene group having 6 to 50 ring carbon atoms (preferably 6 to 25 ring carbon atoms, more preferably 6 to 18 ring carbon atoms) is formed by removing one hydrogen atom from the aryl group.
- a phenylene group, a naphthylene group, a biphenylene group, a terphenylene group, a phenanthrylene group, and a fluorenylene group are preferable.
- At least one, preferably 1 to 5 (more preferably 1 to 3, more preferably 1 to 5 heteroaryl groups having 5 to 50 ring atoms (preferably 5 to 24, more preferably 5 to 13 ring atoms) (Preferably 1 to 2) heteroatoms such as nitrogen, sulfur, oxygen and phosphorus atoms.
- heteroaryl group include pyrrolyl group, furyl group, thienyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyrazolyl group, isoxazolyl group, isothiazolyl group.
- heteroaryl group having 5 to 50 ring atoms a monovalent group obtained by removing one hydrogen atom from any compound represented by the following formula is also preferable.
- A independently represents CR 100 or a nitrogen atom, and R 100 each independently represents a hydrogen atom or a substituent, Each Y independently represents C (R 101 ) (R 102 ), an oxygen atom, a sulfur atom or N (R 103 ); R 101 , R 102 and R 103 each independently represent a hydrogen atom or a substituent, m independently represents 0 or 1, and Y 0 represents a single bond.
- R 101 , R 102 and R 103 each independently represent a hydrogen atom or a substituent, m independently represents 0 or 1, and Y 0 represents a single bond.
- Examples of the aralkyl group having 7 to 51 carbon atoms in total having an aryl group having 6 to 50 ring carbon atoms (preferably 6 to 25, more preferably 6 to 18) include the above aralkyl groups having an aryl group.
- the alkyl group having 1 to 50 carbon atoms (preferably 1 to 18, more preferably 1 to 8) and the aryl group having 6 to 50 ring carbon atoms (preferably 6 to 25, more preferably 6 to 18) are selected.
- Examples of the monosubstituted or disubstituted amino group having a substituent include a monosubstituted or disubstituted amino group having a substituent selected from the above alkyl group and the above aryl group.
- Examples of the alkoxy group having an alkyl group having 1 to 50 carbon atoms include the above alkoxy groups having an alkyl group.
- Examples of the aryloxy group having an aryl group having 6 to 50 ring carbon atoms include the above aryloxy groups having an aryl group.
- alkyl group having 1 to 50 carbon atoms preferably 1 to 18, more preferably 1 to 8
- an aryl group having 6 to 50 ring carbon atoms preferably 6 to 25, more preferably 6 to 18.
- Examples of the monosubstituted, disubstituted or trisubstituted silyl group having a substituent include a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from the above alkyl group and the above aryl group.
- haloalkyl group having 1 to 50 carbon atoms preferably 1 to 18, more preferably 1 to 8
- at least one hydrogen atom of the alkyl group is a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine). And those substituted by an atom).
- alkyl group having 1 to 50 carbon atoms preferably 1 to 18, more preferably 1 to 8 and the aryl group having 6 to 50 ring carbon atoms (preferably 6 to 25, more preferably 6 to 18).
- the sulfonyl group having a selected substituent include a sulfonyl group having a substituent selected from the above alkyl group and the above aryl group.
- the disubstituted phosphoryl group having a selected substituent include a disubstituted phosphoryl group having a substituent selected from the above alkyl group and the above aryl group.
- the partially saturated or saturated ring formed by bonding of adjacent substituents among R 1d to R 15d in the general formula (d) in the general formula (d) is 3 to 50 carbon atoms (preferably 3-6, more preferably 5 or 6) aliphatic hydrocarbon rings are preferred.
- aliphatic hydrocarbon ring having 5 to 50 ring carbon atoms include ring structures selected from cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, and the like. Cyclohexane is preferred.
- aromatic hydrocarbon ring having 6 to 50 ring carbon atoms include benzene ring, naphthalene ring, anthracene ring, benzoanthracene ring, phenanthrene ring, benzophenanthrene ring, fluorene ring, benzofluorene ring, dibenzofluorene ring , Picene ring, tetracene ring, pentacene ring, pyrene ring, chrysene ring, benzochrysene ring, s-indacene ring, as-indacene ring, fluoranthene ring, benzofluoranthene ring, triphenylene ring, benzotriphenylene ring, perylene ring, coronene ring , Dibenzoanthracene ring, etc., preferably benzene ring, naphthalene ring, anthracene ring, fluor
- aromatic heterocyclic ring having 5 to 50 ring atoms include pyrrole ring, pyrazole ring, isoindole ring, benzofuran ring, benzothiophene ring, isobenzofuran ring, dibenzothiophene ring, isoquinoline ring, cinnoline ring, Quinoxaline ring, quinazoline ring, phenanthridine ring, phenanthroline ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, imidazopyridine ring, indole ring, indazole ring, benzimidazole ring, quinoline ring, acridine ring, pyrrolidine Ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan ring, thioph
- Saturated rings formed by combining adjacent substituents among R 1a to R 12a in the general formula (a) include R 8a and R 9a , R 9a and R 10a , R 1a and R 2a , It is preferable to form a ring from one or more pairs selected from R 2a and R 3a , R 3a and R 4a .
- R 8a and R 9a or R 9a and R 10a are preferably aromatic hydrocarbon rings, more preferably benzene rings.
- R 1a and R 2a , R 2a and R 3a , R 3a and R 4a are preferably aromatic hydrocarbon rings, more preferably benzene rings, and dibenzofuran rings, dibenzothiophenes together with the benzene rings to which they are bonded.
- a ring, a 9,9-dimethylfluorene ring, or a carbazole ring may be formed.
- R 8d and R 9d , R 9d and R 10d , R 1d and R 2d , R 2d and R 3d , R 3d and R 4d as a pair of adjacent substituents to be formed are also represented by the above general formula (a) (Subscripts a, b, c, d correspond to subscript a).
- R 1a to R 15a in the general formula (a) and R 1c to R 15c in the general formula (c) is a substituted or unsubstituted ring carbon number of 6
- An aromatic hydrocarbon group (aryl group) having from 60 to 60 or a substituted or unsubstituted heterocyclic group having 3 to 60 ring atoms (heteroaryl group) is preferable.
- X a in the formula (a) represents a N (R 15a)
- R 15a is preferably one X c in the formula (c) indicates the N (R 15c)
- said R 15a And R 15c is more preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 ring carbon atoms (aryl group), wherein R 15a and R 15c are substituted or unsubstituted two or more rings.
- condensation fluoranthene compound of the present invention R 15a in the general formula (a), R 15b in the general formula (b), R 15c in the general formula (c) R 15d and in the general formula (d),
- those which are heterocyclic groups having 3 to 60 ring atoms are also preferred.
- substituted or unsubstituted divalent heterocyclic group having 3 to 60 ring atoms are obtained by removing one hydrogen atom from the above-mentioned heteroaryl group. Things.
- Specific examples of the 50 alkylene groups include those obtained by removing one hydrogen atom from those exemplified as the alkyl group.
- Specific examples of the trivalent organic group represented by L d in the general formula (d) are those obtained by removing one hydrogen atom from the divalent group represented by L b and L c. Is mentioned.
- the condensed fluoranthene compound of the present invention preferably has a ring structure-containing group as a substituent, the substituent represented by R 1a to R 15a in the general formula (a), and R 1b to R in the general formula (b).
- X a in the general formula (a) represents N (R 15a )
- the R 15a is a ring structure-containing group
- X b in the general formula (b) represents N (R 15b ).
- R 15b is a ring structure-containing group
- X c in the general formula (c) is N (R 15c )
- R 15c is a ring structure-containing group
- X d in d) represents N (R 15d )
- R 15d is a ring structure-containing group Is more preferable.
- ring structure-containing group examples include substituted or unsubstituted cycloalkyl groups having 5 to 50 (preferably 3 to 6, more preferably 5 or 6) ring-forming carbon atoms, and substituted or unsubstituted ring-forming carbon atoms having 6 to 50 carbon atoms. (Preferably 6 to 24, more preferably 6 to 18) aryl groups, substituted or unsubstituted aryl groups having 6 to 50 ring carbon atoms (preferably 6 to 24, more preferably 6 to 18).
- sulfonyl having a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (preferably 6 to 24, more preferably 6 to 18) as a substituent.
- Examples of the ring structure-containing group include those having a ring structure-containing group on a substituent, and specific examples of this substituent include those described above.
- those represented by the following general formula (1) are particularly preferred, those represented by the following general formula (1a) are more preferred, and those represented by the following general formula (1b). Particularly preferred.
- Z 21 to Z 25 each independently represents C (R 1 ) or a nitrogen atom.
- R 1 independently represents a hydrogen atom, a substituent, or a bond to Ar 1 .
- Ar 1 each independently represents a hydrogen atom or a substituent, preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl having 5 to 50 ring atoms. It is a group.
- L 11 is a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 ring carbon atoms (arylene group), or a substituted or unsubstituted divalent group having 3 to 60 ring atoms.
- m is an integer of 0 to 5.
- Z 26 to Z 28 each independently represents C (R 1 ) or a nitrogen atom.
- R 1 each independently represents a hydrogen atom or a substituent.
- Ar 2 and Ar 3 each independently represent a hydrogen atom or a substituent, preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring atom having 5 to 50 ring atoms.
- L 12 represents a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 ring carbon atoms (arylene group), or a substituted or unsubstituted divalent group having 3 to 60 ring atoms.
- At least one of Z 26 to Z 28 is preferably a nitrogen atom.
- Ar 4 and Ar 5 each independently represent a hydrogen atom or a substituent, preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted group. And more preferably a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms. It is a group.
- L 13 is a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 ring carbon atoms (arylene group), or a substituted or unsubstituted divalent group having 3 to 60 ring atoms.
- arylene group a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 ring carbon atoms
- heteroarylene group a substituted or unsubstituted divalent group having 3 to 60 ring atoms.
- heteroarylene group A heterocyclic group
- Examples of the substituent represented by Ar 1 in the general formula (1), Ar 2 and Ar 3 in the general formula (1a), and Ar 4 and Ar 5 in the general formula (1b) include the group (A). Is preferably selected from group (B), more preferably selected from group (C). Specific examples of L 11 in the general formula (1), L 12 in the general formula (2), and L 13 in the general formula (3) include L b and the general formula ( The same thing as Lc in c) is mentioned.
- Ar 15 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.
- L 14 represents a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 ring carbon atoms (arylene group), or a substituted or unsubstituted divalent aromatic group having 3 to 60 ring atoms.
- a heterocyclic group (heteroarylene group) is shown.
- Examples of the aryl group having 6 to 50 ring carbon atoms as Ar 15 in the general formula (2) include those listed as the aryl groups having 6 to 50 ring carbon atoms in the general formulas (a) to (d). The same thing is mentioned.
- the heteroaryl group having 5 to 50 ring atoms as Ar 15 in the general formula (2) is a heteroaryl group having 5 to 50 ring atoms in the general formulas (a) to (d). The thing similar to what was mentioned is mentioned.
- Specific examples of L 14 in the general formula (1) include the same as L b in the general formula (b) and L c in the general formula (c).
- Ar 15 in the general formula (2) includes phenyl group, naphthyl group, biphenylyl group, terphenylyl group, phenanthryl group, benzophenanthryl group, fluorenyl group, benzofluorenyl group, chrysenyl group, benzocrisenyl group, fluoranthenyl.
- L 14 in the general formula (2) is particularly preferably a single bond, a phenylene group, a naphthylene group, a biphenylene group, a terphenylene group, a phenanthrylene group, or a fluorenylene group.
- the material for an organic EL device of the present invention contains the condensed fluoranthene compound.
- the content of the condensed fluoranthene compound in the organic EL device material of the present invention is not particularly limited, and may be, for example, 1% by mass or more, preferably 10% by mass or more, and preferably 50% by mass or more. Is more preferably 80% by mass or more, and particularly preferably 90% by mass or more.
- the material for an organic EL device of the present invention is useful as a material in an organic EL device, and can be used as, for example, a host material and a dopant material in a light emitting layer of a fluorescent light emitting unit or a host material in a light emitting layer of a phosphorescent light emitting unit. .
- a host material and a dopant material in a light emitting layer of a fluorescent light emitting unit or a host material in a light emitting layer of a phosphorescent light emitting unit. In both the fluorescent light emitting unit and the phosphorescent light emitting unit, an anode-side organic thin film layer provided between the anode of the organic EL element and the light emitting layer, or a cathode provided between the cathode of the organic EL element and the light emitting layer.
- the “light emitting unit” refers to a minimum unit that includes one or more organic layers, one of which is a light emitting layer, and can emit light by recombination of injected holes and electrons.
- the organic EL device of the present invention has an organic thin film layer containing a light emitting layer between a cathode and an anode, and at least one of the organic thin film layers includes the organic EL device material described above. To do.
- the organic thin film layer containing the organic EL element material described above include an anode-side organic thin film layer (hole transport layer, hole injection layer, etc.) provided between the anode and the light emitting layer, a light emitting layer, and a cathode.
- Examples include, but are not limited to, a cathode side organic thin film layer (electron transport layer, electron injection layer, etc.), a space layer, a barrier layer and the like provided between the light emitting layer and the light emitting layer.
- the above-mentioned organic EL element material may be contained in any of the above layers.
- the organic EL element of the present invention may be a fluorescent or phosphorescent monochromatic light emitting element, a fluorescent / phosphorescent hybrid white light emitting element, or a simple type having a single light emitting unit.
- a tandem type having a plurality of light emitting units may be used, and among them, a phosphorescent type is preferable.
- the “light emitting unit” refers to a minimum unit that includes one or more organic layers, one of which is a light emitting layer, and can emit light by recombination of injected holes and electrons.
- typical element configurations of simple organic EL elements include the following element configurations.
- 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 (
- Each phosphorescent or fluorescent light-emitting layer may have a different emission color.
- 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) / Examples include a layer configuration such as an electron transport layer.
- An electron barrier layer may be appropriately provided between each light emitting layer and the hole transport layer or space layer.
- a hole blocking layer may be appropriately provided between each light emitting layer and the electron transport layer.
- the following element structure can be mentioned as a typical element structure of a tandem type organic EL element.
- the intermediate layer is generally called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, or an intermediate insulating layer, and has electrons in the first light emitting unit and holes in the second light emitting unit.
- a known material structure to be supplied can be used.
- FIG. 1 shows a schematic configuration of an example of the organic EL element of the present invention.
- the organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and a light emitting unit 10 disposed between the anode 3 and the cathode 4.
- the light emitting unit 10 includes a light emitting layer 5 including at least one phosphorescent light emitting layer including a phosphorescent host material and a phosphorescent dopant (phosphorescent material).
- a hole injection / transport layer 6 or the like may be formed between the light emitting layer 5 and the anode 3, and an electron injection / transport layer 7 or the like may be formed between the light emitting layer 5 and the cathode 4.
- an electron barrier layer may be provided on the anode 3 side of the light emitting layer 5, and a hole barrier layer may be provided on the cathode 4 side of the light emitting layer 5.
- 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.
- the fluorescent host and the phosphorescent host are not distinguished only by the 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.
- the organic EL element of the present invention 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 those using 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 plate include those using polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, polysulfone and the like as raw materials.
- 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 ⁇ / ⁇ 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 includes a host material and a dopant material.
- the host material mainly has a function of encouraging recombination of electrons and holes and confining excitons in the light emitting layer, and the dopant material efficiently emits excitons obtained by recombination. It has a function.
- the host material mainly has a function of confining excitons generated by the dopant in the light emitting layer.
- the light emitting layer employs, for example, a double host (also referred to as host / cohost) that adjusts the carrier balance in the light emitting layer 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.
- a light emitting layer can be formed by well-known methods, such as a vapor deposition method, a spin coat method, LB method, for example.
- 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 deposited film is a thin film formed by deposition from a material compound in a gas phase state or a film formed by solidifying from a material compound in a solution state or a liquid phase state.
- the thin film (molecular accumulation film) formed by the LB method can be classified by the difference in the aggregation structure and the higher-order structure, and the functional difference resulting therefrom.
- the phosphorescent dopant (phosphorescent material) 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, but Ir, Pt, Os, Au, Cu, An organometallic complex containing at least one metal selected from Re and Ru 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 preferred in that the phosphorescent quantum yield is high and the external quantum efficiency of the light emitting device can be further improved, and an iridium complex, an osmium complex, or a platinum complex.
- iridium complexes and platinum complexes are more preferable, and orthometalated iridium complexes are particularly preferable.
- 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, 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.
- 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 organic EL device material of the present invention is useful as a phosphorescent host, but a compound other than the organic EL device material of the present invention can also be appropriately selected as the phosphorescent host according to the above purpose.
- the organic EL device material of the present invention and other compounds may be used in combination as a phosphorescent host material in the same light emitting layer, and when there are a plurality of light emitting layers, the phosphorescent host of one of the light emitting layers.
- the material for an organic EL device of the present invention may be used as a material, and a compound other than the material for an organic EL device of the present invention may be used as a phosphorescent host material for another light emitting layer.
- the organic EL device material of the present invention can be used for organic layers other than the light emitting layer. In that case, a compound other than the organic EL device material of the present invention is used as the phosphorescent host of the light emitting layer. May be.
- compounds other than the organic EL device material of the present invention and 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, porphyrins Compounds, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluorenylidene derivatives And metal complexes of heterocycl
- the organic EL device of the present invention 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.
- an anthracene derivative is preferable as the host material
- an arylamine derivative is preferable as the dopant.
- suitable materials described in International Publication No. 2010/134350 and International Publication No. 2010/134352 are selected.
- the material for an organic EL device of the present invention may be used as a fluorescent light emitting material for the fluorescent light emitting layer or as a host material 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.
- an anthracene derivative represented by the formula (10) is preferable.
- 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 the definition of R 81 to R 88.
- a is an integer of 1 to 7.
- R 81 to R 88 are preferably the same as described above.
- the preferred 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.
- a 20 aryl group is more preferred, and an aryl group having 6 to 12 ring carbon atoms is particularly preferred.
- 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.
- a group is more preferable, and a phenyl group and a naphthyl group are particularly 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.
- the group is more preferable, and the pyrenyl group is particularly preferable.
- the light emitting layer may be a double host (also referred to as a host / cohost). Specifically, the carrier balance in the light emitting layer may be adjusted by combining an electron transporting host and a hole transporting host in the light emitting layer. Moreover, it is good also as a double dopant.
- each dopant emits light by adding two or more dopant materials having a high quantum yield. For example, a yellow light emitting layer may be realized by co-evaporating a host, a red dopant, and a green dopant.
- a light emitting layer may contain a hole transport material, an electron transport material, and a polymer binder as needed.
- the thickness of the light emitting layer is preferably 5 to 50 nm, more preferably 7 to 50 nm, and most preferably 10 to 50 nm. If the thickness is less than 5 nm, it is difficult to form a light emitting layer, and it may be difficult to adjust the chromaticity. If the thickness exceeds 50 nm, the driving voltage may increase.
- the organic EL device of the present invention preferably has an electron donating dopant in the interface region between the cathode and the light emitting unit. 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 means a material containing a metal having a work function of 3.8 eV or less, and specific examples thereof include alkali metals, alkali metal complexes, alkali metal compounds, alkaline earth metals, alkaline earths. Examples thereof include at least one selected from metal complexes, alkaline earth metal compounds, rare earth metals, rare earth metal complexes, rare earth metal compounds, and the like.
- alkali metal examples include Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV), Cs (work function: 1.95 eV), and the like.
- a function of 2.9 eV or less is particularly preferable. Of these, K, Rb, and Cs are preferred, Rb and Cs are more preferred, and Cs is most preferred.
- alkaline earth metals include Ca (work function: 2.9 eV), Sr (work function: 2.0 eV to 2.5 eV), Ba (work function: 2.52 eV), and the like. The thing below 9 eV is especially preferable.
- rare earth metals examples include Sc, Y, Ce, Tb, Yb, and the like, and those having a work function of 2.9 eV or less are particularly preferable.
- alkali metal compound examples include alkali oxides such as Li 2 O, Cs 2 O, and K 2 O, and alkali halides such as LiF, NaF, CsF, and KF, and LiF, Li 2 O, and NaF are preferable.
- alkaline earth metal compound examples include BaO, SrO, CaO, and Ba x Sr 1-x O (0 ⁇ x ⁇ 1), Ba x Ca 1-x O (0 ⁇ x ⁇ 1) mixed with these. BaO, SrO, and CaO are preferable.
- the rare earth metal compound, YbF 3, ScF 3, ScO 3, Y 2 O 3, Ce 2 O 3, GdF 3, TbF 3 and the like, YbF 3, ScF 3, TbF 3 are preferable.
- the alkali metal complex, alkaline earth metal complex, and rare earth metal complex are not particularly limited as long as each metal ion contains at least one of an alkali metal ion, an alkaline earth metal ion, and a rare earth metal ion.
- the ligand includes quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxydiaryl oxadiazole, hydroxydiaryl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxybenzotriazole, Hydroxyfulborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, ⁇ -diketones, azomethines, and derivatives thereof are preferred, but not limited thereto.
- the electron donating dopant it is preferable to form a layered or island shape in the interface region.
- a forming method while depositing an electron donating dopant by resistance heating vapor deposition, an organic compound (light emitting material or electron injecting material) that forms an interface region is simultaneously deposited, and the electron donating dopant is dispersed in the organic compound.
- the electron donating dopant is formed in a layered form
- the reducing dopant is vapor-deposited by a resistance heating vapor deposition method. .1 nm to 15 nm.
- the electron donating dopant is formed in an island shape
- the electron donating dopant is deposited by resistance heating vapor deposition alone, preferably The island is formed with a thickness of 0.05 nm to 1 nm.
- the electron transport layer 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.
- an organic layer close to the cathode may be defined as an electron injection layer.
- the electron injection layer has a function of efficiently injecting electrons from the cathode into the organic layer unit.
- the organic EL device material of the present invention can also be used as an electron transport material contained in the 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 particularly 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 formula (A) are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, an amino group, a hydrocarbon group having 1 to 40 carbon atoms, or an alkoxy group having 1 to 40 carbon atoms. , 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 or a deuterium atom.
- the arylamino group is represented as —NAr 1 Ar 2, and Ar 1 and Ar 2 each independently represents 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 or a deuterium 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, a deuterium atom, or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other are cyclic structures May be formed.
- R 13 to R 27 are each independently a hydrogen atom, a deuterium atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other are An annular structure 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 represented by R 2 to R 7 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 includes a tetramethylene group, a pentamethylene group, a hexamethylene group, and the like. Examples include a methylene group, diphenylmethane-2,2′-diyl group, diphenylethane-3,3′-diyl group, and 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 the following can be mentioned.
- Ar 17 , Ar 18 , Ar 19 , Ar 21 , Ar 22 and Ar 25 each represent a substituted or unsubstituted aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 50 carbon atoms
- Ar 17 and Ar 18 , Ar 19 and Ar 21 , Ar 22 and Ar 25 may be the same or different.
- 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.
- electron transfer compounds those having good thin film forming properties are preferably used.
- Specific examples of these electron transfer compounds include the following.
- 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. Examples thereof include a 5-membered ring or 6-membered ring containing a skeleton represented by the following formula (B) and a structure represented by the following formula (C).
- 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 represents 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 is selected from the following group, for example.
- Ar 1 is selected from, for example, arylanthranyl groups of the following formulas (D2) and (D3).
- R 1 to R 14 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, or an alkoxy having 1 to 20 carbon atoms.
- R 1 to R 8 may be nitrogen-containing heterocyclic derivatives each of which is a hydrogen atom or a deuterium atom.
- Ar 2 is selected from the following group, for example.
- the following compounds are also preferably used as the nitrogen-containing aromatic polycyclic organic compound as the electron transporting compound.
- R 1 to R 4 each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted aliphatic group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon number of 3 to 20
- X 1 and X 2 are each independently Represents an oxygen atom, a sulfur atom, or a dicyanomethylene group.
- the following compounds are 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 deuterium atom, a saturated or unsaturated alkoxy 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 or a deuterium 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 particularly 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 's 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 divalent or substituted or unsubstituted divalent atom 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 Group 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. Moreover, it is preferable to use an insulator or a semiconductor as an inorganic compound in addition to the nitrogen-containing ring derivative as a component of the electron injection layer that can be provided adjacent to the electron transport layer. If the 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 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 electron injection layer is preferably a microcrystalline or amorphous insulating thin film. If the 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 electron injection layer in the present invention is preferable even if it contains the above-mentioned electron donating dopant.
- 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 unit.
- the organic EL device material of the present invention can also be used as a hole transport material contained in the hole transport 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 represented by the following formula (J) is also preferably used for forming the hole transport layer.
- the hole transport layer of the organic EL device of the present invention 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 anode side of the hole transport layer or 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 are each independently a cyano group, —CONH 2 , 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 F4TCNQ (2,3,5,6-Tetrafluoro) as a hole transport material.
- an acceptor material such as ⁇ 7,7,8,8-tetracyanoquinodimethane
- 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. Examples of the material used for the space layer include the same materials as those used for the above-described hole transport layer. As the material for the space layer, the organic EL device material of the present invention can also be used.
- the organic EL device of the present invention 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 organic EL device material of the present invention can also be used.
- 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 ETd and the triplet energy of the compound used as the triplet barrier layer is ETTB, ETd ⁇ ETTB If present, the triplet exciton of the phosphorescent dopant is confined (cannot move to other molecules) in terms of energy, and the energy deactivation path other than the emission on the dopant is interrupted, and the phosphor emits light with high efficiency.
- the organic EL element material of the present invention can be used as a material for a triplet barrier layer having a TTF element structure described in International Publication WO2010 / 134350A1.
- the electron mobility of the material constituting the triplet barrier layer is preferably 10 ⁇ 6 cm 2 / Vs or more in the range of the electric field strength of 0.04 to 0.5 MV / cm.
- the electron mobility is determined by impedance spectroscopy.
- the electron mobility of the electron injection layer is preferably 10 ⁇ 6 cm 2 / Vs 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 organic electroluminescence element of the present invention can be used for display devices such as an organic EL panel module, display devices such as a television, a mobile phone, or a personal computer, and electronic equipment such as a light emitting device for lighting or a vehicle lamp.
- display devices such as an organic EL panel module
- display devices such as a television, a mobile phone, or a personal computer
- electronic equipment such as a light emitting device for lighting or a vehicle lamp.
- Example 28 (Synthesis of Compound 28) (1) Synthesis of 2-bromo-3-nitrofluoranthene 300 mL of acetonitrile was added to 29.6 g of 2-bromo-3-fluoranthamine synthesized by the method described in WO2010 / 123153 and 0.83 g of potassium iodide, The mixture was stirred at room temperature and 50 g of a 70% by mass aqueous solution of t-butyl hydroperoxide was added dropwise. The reaction solution was continuously heated and stirred at 80 ° C. for 15 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and quenched with a saturated aqueous sodium thiosulfate solution.
- reaction solution was extracted with toluene, and the aqueous layer was removed. After the organic layer was dried over magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 14.7 g of 2-bromo-3-nitrofluoranthene.
- intermediate (G) was synthesized in the same manner using compound (G) instead of compound 1 and 3- (3-bromophenyl) fluoranthene instead of intermediate (B).
- intermediate (G) was synthesized in the same manner using Intermediate (G) instead of Compound 1 and Intermediate (C) instead of Intermediate (B).
- the compound 28 was synthesized by the same method using 4-dibenzothiopheneboronic acid instead of 1-naphthaleneboronic acid.
- intermediate (I) was synthesized in the same manner using compound (1) instead of compound 1 and 3- (3-bromophenyl) fluoranthene instead of intermediate (B).
- intermediate (J) was synthesized in the same manner as in Example 1, except that intermediate (J) was used instead of compound 1 and 2-bromotriphenylene was used instead of intermediate (B).
- compound 28 was synthesized in the same manner using benzo [b] naphtho [1,2-d] thiophene-5-boronic acid synthesized by a known method instead of 1-naphthaleneboronic acid. did.
- intermediate (K) was synthesized in the same manner using Compound (K) instead of Compound 1 and 3- (3-bromophenyl) fluoranthene instead of Intermediate (B).
- intermediate (L) was synthesized in the same manner using intermediate (L) instead of compound 1 and intermediate (M) synthesized by a known method instead of intermediate (B).
- Example 50 Manufacture of an organic EL device
- a glass substrate with an ITO transparent electrode of 25 mm ⁇ 75 mm ⁇ thickness 1.1 mm (manufactured by Geomatek Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes.
- the cleaned glass substrate with a transparent electrode line of 130 nm is attached to a substrate holder of a vacuum evaporation apparatus, and first the first hole transport material is formed so as to cover the transparent electrode on the surface on which the transparent electrode line is formed.
- the following compound HT-1 was deposited as a first hole transport layer having a thickness of 45 nm.
- the following compound HT-2 was deposited as a second hole transport material to form a second hole transport layer having a thickness of 10 nm. Further, on the second hole transport layer, the compound 2 obtained in Example 2 as a host material and the following compound RD-1 as a phosphorescent material were co-evaporated to form a phosphorescent layer having a thickness of 40 nm. Filmed. The concentration of Compound RD-1 in the light emitting layer was 5.0% by mass. This co-deposited film functions as a light emitting layer. Following the formation of the light emitting layer, the following compound ET-1 was formed to a thickness of 40 nm. This compound ET-1 film functions as a first electron transport layer.
- LiF was used as an electron injecting electrode (cathode) at a film forming rate of 0.01 nm / sec, and the film thickness was 1 nm.
- Metal Al was vapor-deposited on this LiF film, and a metal cathode was formed with a film thickness of 80 nm to produce an organic EL device.
- the compounds used in Example 50 and Comparative Example 1 are shown below.
- the light emission characteristics of the organic EL device obtained as described above were evaluated as follows.
- the triplet energy was measured as follows.
- Table 1 shows the results obtained by measuring the external quantum efficiency of the obtained organic EL device at room temperature and DC constant current drive (current density 10 mA / cm 2 ) using a luminance meter (Spectral Luminance Radiometer CS-1000 manufactured by Minolta). And in Table 2.
- Triplet energy was determined by the following method.
- the phosphorescence measurement sample placed in the quartz cell was cooled to 77 [K], the excitation light was irradiated onto the phosphorescence measurement sample, and the phosphorescence intensity was measured while changing the wavelength. Is the phosphorescence intensity, and the horizontal axis is the wavelength.
- a tangent line was drawn with respect to the rising edge of the phosphorescence spectrum on the short wavelength side, and a wavelength value ⁇ edge [nm] at the intersection of the tangent line and the horizontal axis was obtained.
- a value obtained by converting this wavelength value into an energy value by the following conversion formula was defined as EgT.
- the maximum point having a peak intensity of 10% or less of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and has the maximum slope value closest to the maximum value on the shortest wavelength side.
- the tangent drawn at the point where the value is taken is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side.
- an F-4500 spectrofluorometer main body manufactured by Hitachi High-Technology Co., Ltd. and optional equipment for low temperature measurement were used. Note that the measurement device is not limited to this, and the measurement may be performed by combining a cooling device and a cryogenic container, an excitation light source, and a light receiving device.
- Example 50 an organic EL device was produced in the same manner as in Example 50 except that the light emitting layer was formed using Comparative Compound 1 instead of using Compound 2 as the host material of the light emitting layer.
- Table 1 shows the measurement results of the external quantum efficiency of the organic EL device and the triplet energy measurement results of Comparative Compound 1.
- the condensed fluoranthene compound of the present invention has a triplet energy higher than that of Comparative Compound 1. Even in the same condensed fluoranthene compound, a high triplet level can be maintained by different condensed ring modes, so that it is possible to maintain high efficiency. Actually, it can be seen from the results in Table 1 that the external quantum efficiency is high. Furthermore, in the compound 2 which is a condensed fluoranthene derivative of the present invention, as compared with the condensed ring mode of the comparative compound 1, the twist on the substituent on N and the condensed fluoranthene mother skeleton is large and almost perpendicular.
- Example 51 The glass substrate with a 130 nm transparent electrode line after cleaning used in Example 50 is mounted on a substrate holder of a vacuum evaporation apparatus, and first, the transparent electrode is covered on the surface on which the transparent electrode line is formed.
- the following compound HA-1 was deposited as a hole injection material to form a 10 nm-thick hole injection layer.
- the following compound HT-3 was deposited as a first hole transport material to form a first hole transport layer having a thickness of 20 nm.
- the following compound HT-4 was deposited as a second hole transport material to form a second hole transport layer having a thickness of 10 nm.
- Example 10 the compound 10 obtained in Example 10 as a host material and the following compound RD-1 as a phosphorescent material were co-evaporated to form a phosphorescent layer having a thickness of 40 nm. Filmed. The concentration of Compound RD-1 in the light emitting layer was 5.0% by mass. This co-deposited film functions as a light emitting layer. Following the formation of the light emitting layer, the following compound ET-1 was formed to a film thickness of 45 nm. This compound ET-1 film functions as a first electron transport layer. Next, LiF was used as an electron injecting electrode (cathode) at a film forming rate of 0.01 nm / sec, and the film thickness was 1 nm. Metal Al was vapor-deposited on this LiF film, and a metal cathode was formed with a film thickness of 80 nm to produce an organic EL device. The compounds used in Examples 51 to 58 and Comparative Examples 2 and 3 are shown below.
- Example 51 a device was prepared and evaluated in the same manner as in Example 51 except that the compounds listed in Table 2 were used instead of Compound 10. The results are shown in Table 2.
- Example 51 an organic EL device was produced in the same manner as in Example 51 except that the light emitting layer was formed using Comparative Compounds 2 and 3 instead of using Compound 10 as the host material of the light emitting layer. Evaluation was performed. The results are shown in Table 2.
- the organic luminescence device using the condensed fluoranthene compound of the present invention uses the condensed fluoranthene compound of Comparative Examples 2 and 3. It can be confirmed that the external quantum efficiency is higher than that of the conventional device.
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Abstract
Description
また、有機EL素子は、発光層に種々の発光材料を用いることにより、多様な発光色を得ることが可能であることから、ディスプレイなどへの実用化研究が盛んである。特に赤色、緑色、青色の三原色の発光材料の研究が最も活発であり、特性向上を目指して鋭意研究がなされている。
しかしながら、有機EL素子の分野においては、さらなる素子性能の向上を目指すため、新たな材料系の開発が求められている。
本発明者らが鋭意検討した結果、上記化合物とは縮合位置や向きが異なる縮合フルオランテン化合物を有機EL素子用材料として提供し得ることを見出した。
[1]下記一般式(a)で表される縮合フルオランテン化合物。
R1a~R15aは、それぞれ独立に、水素原子または置換基を示し、R1a~R15aのうち隣接する置換基同士は、互いに結合して飽和または不飽和の環構造を形成してもよい。]
[2]上記[1]に記載の縮合フルオランテン化合物を含有する有機エレクトロルミネッセンス素子用材料。
[3]陰極と陽極間に少なくとも発光層を含む一層又は複数層からなる有機薄膜層が挟持されている有機エレクトロルミネッセンス素子において、該有機薄膜層の少なくとも1層が、上記[1]又は[2]に記載の縮合フルオランテン化合物を含有する有機エレクトロルミネッセンス素子。
[4]上記[3]に記載の有機エレクトロルミネッセンス素子を備える電子機器。
これらの置換基は、さらに上述の任意の置換基により置換されていてもよい。また、任意の置換基同士が結合して環を形成していてもよい。
本発明の縮合フルオランテン化合物は、下記一般式(a)で表される。
R1a~R15aは、それぞれ独立に、水素原子または置換基を示し、R1a~R15aのうち隣接する置換基同士は、互いに結合して飽和または不飽和の環構造を形成してもよい。]
R1b~R15bは、それぞれ独立に、水素原子、置換基、又はLbとの結合手を示し、R1b~R15bのうち隣接する置換基同士は、互いに結合して飽和または不飽和の環構造を形成してもよい。
Lbは、単結合または、2価の連結基を示す。]
Lbで表される2価の連結基の具体例としては、置換もしくは無置換の環形成炭素数6~60の芳香族複素環基(アリーレン基)、置換もしくは無置換の環形成原子数3~60の複素環基(ヘテロアリーレン基)、置換もしくは無置換の炭素数1~50のアルキレン基等が挙げられる。
R1d~R15dは、それぞれ独立に、水素原子、置換基、又はLdとの結合手を示し、R1d~R15dのうち隣接する置換基同士は、互いに結合して飽和または不飽和の環構造を形成してもよい。
Ldは、3価の有機基を示す。]
R1c~R15cは、それぞれ独立に、水素原子、置換基又はLcとの結合手を示し、R1c~R15cのうち隣接する置換基同士は、互いに結合して飽和または不飽和の環構造を形成してもよい。
Ycは、置換もしくは無置換の環形成炭素数6~60のp価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3~60のp価の複素環基を示す。
Lcは、単結合、置換もしくは無置換の環形成炭素数6~60の2価の芳香族炭化水素基(アリーレン基)、置換もしくは無置換の環形成原子数3~60の2価の複素環基(ヘテロアリーレン基)、または、置換もしくは無置換の炭素数1~50のアルキレン基を示す。
pは、1~6の整数を示し、好ましくは1~3、より好ましくは1又は2である。]
また、前記環形成炭素数6~50(好ましくは環形成炭素数6~25、より好ましくは環形成炭素数6~18)のアリーレン基としては、上記アリール基より1個の水素原子を除いてなるものが挙げられ、フェニレン基、ナフチレン基、ビフェニレン基、タ-フェニレン基、フェナントリレン基、フルオレニレン基が好ましい。
Yは、それぞれ独立に、C(R101)(R102)、酸素原子、硫黄原子又はN(R103)を表し、
R101、R102及びR103は、それぞれ独立に、水素原子又は置換基を表わし、mは、それぞれ独立に、0または1を表し、Y0は単結合を表す。]
上記式中における置換基としては、上述のものと同様のものが挙げられる。
前記炭素数1~50(好ましくは1~18、より好ましくは1~8)のアルキル基及び環形成炭素数6~50のアリール基(好ましくは6~25、より好ましくは6~18)から選ばれる置換基を有するモノ置換又はジ置換アミノ基としては、上記アルキル基及び上記アリール基から選ばれる置換基を有するモノ置換又はジ置換アミノ基が挙げられる。
前記炭素数1~50(好ましくは1~18、より好ましくは1~8)のアルキル基を有するアルコキシ基としては、上記アルキル基を有するアルコキシ基が挙げられる。
前記環形成炭素数6~50(好ましくは6~25、より好ましくは6~18)のアリール基を有するアリールオキシ基としては、上記アリール基を有するアリールオキシ基が挙げられる。
前記炭素数1~50(好ましくは1~18、より好ましくは1~8)のハロアルキル基としては、上記アルキル基の水素原子の1以上が、ハロゲン原子(フッ素原子、塩素原子、臭素原子、ヨウ素原子)により置換されたものが挙げられる。
前記炭素数1~50(好ましくは1~18、より好ましくは1~8)のアルキル基及び前記環形成炭素数6~50(好ましくは6~25、より好ましくは6~18)のアリール基から選ばれる置換基を有するジ置換ホスフォリル基としては、上記アルキル基及び上記アリール基から選ばれる置換基を有するジ置換ホスフォリル基が挙げられる。
また、前記一般式(a)におけるR1a~R15aのうち隣接する置換基同士が互いに結合して形成する不飽和の環、前記一般式(b)におけるR1b~R15bのうち隣接する置換基同士が互いに結合して形成する不飽和の環、前記一般式(c)におけるR1c~R15cのうち隣接する置換基同士が互いに結合して形成する不飽和の環、前記一般式(d)におけるR1d~R15dのうち隣接する置換基同士が互いに結合して形成する不飽和の環としては、それぞれ、環形成炭素数6~50(好ましくは6~24、より好ましくは6~18)の芳香族炭化水素環、又は環形成原子数5~50(好ましくは5~24、より好ましくは5~13)の芳香族複素環が好ましい。
また、前記一般式(b)のR1b~R12bのうち互いに結合して飽和の環を形成する隣接する置換基同士の組としてのR8bとR9b、R9bとR10b、R1bとR2b、R2bとR3b、R3bとR4b、前記一般式(c)のR1cとR12cのうち互いに結合して飽和の環を形成する隣接する置換基同士の組としてのR8cとR9c、R9cとR10c、R1cとR2c、R2cとR3c、R3cとR4c、前記一般式(d)のR1dとR12dのうち互いに結合して飽和の環を形成する隣接する置換基同士の組としてのR8dとR9d、R9dとR10d、R1dとR2d、R2dとR3d、R3dとR4d、についても、上記一般式(a)と同様である(添え字aに添え字b、c、dを対応させる)。
本発明の縮合フルオランテン化合物は、前記一般式(a)におけるXaがN(R15a)を示し、前記一般式(c)におけるXcがN(R15c)を示すものが好ましく、該R15a及びR15cが、置換もしくは無置換の環形成炭素数6~60の芳香族炭化水素基(アリール基)を示すものがより好ましく、該R15a及びR15cが、置換もしくは無置換の2環以上が縮環してなる環形成炭素数10~60の縮合芳香族炭化水素基であるものがさらに好ましい。
また、本発明の縮合フルオランテン化合物は、前記一般式(a)におけるR15a、前記一般式(b)におけるR15b、前記一般式(c)におけるR15c、及び前記一般式(d)におけるR15dが、環形成原子数3~60の複素環基(ヘテロアリール基)であるものも好ましい。
上記一般式(b)においてLbで表される置換もしくは無置換の環形成原子数3~60の2価の複素環基(ヘテロアリーレン基)、及び上記一般式(c)においてLcで表される置換もしくは無置換の環形成原子数3~60の2価の複素環基(ヘテロアリーレン基)の具体例としては、上記へテロアリール基として挙げられたものから水素原子を1つ除いてなるものが挙げられる。
上記一般式(b)においてLbで表される置換もしくは無置換の炭素数1~50のアルキレン基、及び上記一般式(c)においてLcで表される置換もしくは無置換の炭素数1~50のアルキレン基の具体例としては、上記アルキル基として挙げられたものから水素原子を1つ除いてなるものが挙げられる。
また、上記一般式(d)においてLdで表される3価の有機基の具体例としては、上記Lb及びLcで表される2価の基より水素原子を1つ除いてなるものが挙げられる。
縮合フルオランテン化合物が環構造含有基を有することにより、有機EL素子用材料として用いた場合に、該材料を含む有機薄膜の均一性、緻密性が向上するなどの効果を奏する。
環構造含有基としては、置換もしくは無置換の環形成炭素数5~50(好ましくは3~6、より好ましくは5又は6)のシクロアルキル基、置換もしくは無置換の環形成炭素数6~50(好ましくは6~24、より好ましくは6~18)のアリール基、置換もしくは無置換の環形成炭素数6~50(好ましくは6~24、より好ましくは6~18)のアリール基を有する総炭素数7~51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のアリール基(好ましくは6~24、より好ましくは6~18)を置換基として有するモノ又はジアリールアミノ基、置換もしくは無置換の環形成炭素数6~50(好ましくは6~24、より好ましくは6~18)のアリール基を有するアリールオキシ基、置換もしくは無置換の環形成炭素数6~50(好ましくは6~24、より好ましくは6~18)のアリール基を置換基として有するモノ、ジ、又はトリアリールシリル基、置換もしくは無置換の環形成原子数5~50(好ましくは5~24、より好ましくは5~13)のヘテロアリール基、置換もしくは無置換の環形成炭素数6~50(好ましくは6~24、より好ましくは6~18)のアリール基を置換基として有するスルフォニル基、置換もしくは無置換の環形成炭素数6~50(好ましくは6~24、より好ましくは6~18)のアリール基を置換基として有するホスフォニル基から選択される基を含有する基が挙げられ、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、又は置換もしくは無置換の環形成炭素数6~50のアリール基を有するモノ又はジアリールアミノ基を含有する基がより好ましい。これらの基の詳細は、上述のものと同様である。
上記環構造含有基としては、置換基上に環構造含有基を有するものも包含され、この置換基の具体例としては、上述したものが挙げられる。
R1は、それぞれ独立に、水素原子、置換基又はAr1への結合手を表す。
Ar1は、それぞれ独立に、水素原子又は置換基を表し、好ましく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。
L11は、単結合、置換もしくは無置換の環形成炭素数6~60の2価の芳香族炭化水素基(アリーレン基)、または、置換もしくは無置換の環形成原子数3~60の2価の複素環基(ヘテロアリーレン基)を示す。
mは0~5の整数である。]
R1は、それぞれ独立に、水素原子、又は置換基を表す。
Ar2及びAr3は、それぞれ独立に、水素原子又は置換基を表し、好ましく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。
L12は、単結合、置換もしくは無置換の環形成炭素数6~60の2価の芳香族炭化水素基(アリーレン基)、または、置換もしくは無置換の環形成原子数3~60の2価の複素環基(ヘテロアリーレン基)を示す。]
Z26~Z28の少なくとも1つが窒素原子であることが好ましい。
L13は、単結合、置換もしくは無置換の環形成炭素数6~60の2価の芳香族炭化水素基(アリーレン基)、または、置換もしくは無置換の環形成原子数3~60の2価の複素環基(ヘテロアリーレン基)を示す。]
上記一般式(1)におけるL11、上記一般式(2)におけるL12、及び上記一般式(3)におけるL13の具体例としては、上述の一般式(b)におけるLb及び一般式(c)におけるLcと同様のものが挙げられる。
Ar15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。
L14は、単結合、置換もしくは無置換の環形成炭素数6~60の2価の芳香族炭化水素基(アリーレン基)、又は置換もしくは無置換の環形成原子数3~60の2価の複素環基(ヘテロアリーレン基)を示す。]
上記一般式(1)におけるL14の具体例としては、上述の一般式(b)におけるLb及び一般式(c)におけるLcと同様のものが挙げられる。
一般式(2)におけるL14としては、単結合、フェニレン基、ナフチレン基、ビフェニレン基、タ-フェニレン基、フェナントリレン基、フルオレニレン基が特に好ましい。
本発明の有機EL素子用材料は、上記縮合フルオランテン化合物を含む。本発明の有機EL素子用材料における縮合フルオランテン化合物の含有量は、特に制限されず、例えば、1質量%以上であればよく、10質量%以上であることが好ましく、50質量%以上であることがより好ましく、80質量%以上であることがさらに好ましく、90質量%以上であることが特に好ましい。
本発明の有機EL素子用材料は、有機EL素子における材料として有用であり、例えば、蛍光発光ユニットの発光層におけるホスト材料及びドーパント材料や、燐光発光ユニットの発光層におけるホスト材料として用いることができる。また、蛍光発光ユニット及び燐光発光ユニットのいずれにおいても、有機EL素子の陽極と発光層との間に設けられる陽極側有機薄膜層や、有機EL素子の陰極と発光層との間に設けられる陰極側有機薄膜層の材料、すなわち、正孔輸送層、正孔注入層、電子輸送層、電子注入層、正孔阻止層、電子阻止層等の材料としても有用である。
ここで、「発光ユニット」とは、一層以上の有機層を含み、そのうちの一層が発光層であり、注入された正孔と電子が再結合することにより発光することができる最小単位をいう。
次に、本発明の有機EL素子について説明する。
本発明の有機EL素子は、陰極と陽極の間に発光層を含有する有機薄膜層を有し、この有機薄膜層のうちの少なくとも1層が前述した有機EL素子用材料を含むことを特徴とする。
前述の有機EL素子用材料が含まれる有機薄膜層の例としては、陽極と発光層との間に設けられる陽極側有機薄膜層(正孔輸送層、正孔注入層等)、発光層、陰極と発光層との間に設けられる陰極側有機薄膜層(電子輸送層、電子注入層等)、スペース層、障壁層等が挙げられるが、これらに限定されるものではない。前述の有機EL素子用材料は、上記いずれの層に含まれていてもよく、例えば、蛍光発光ユニットの発光層におけるホスト材料やドーパント材料、燐光発光ユニットの発光層におけるホスト材料、発光ユニットの正孔輸送層、電子輸送層等として用いることができる。
(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)
なお、各発光層と正孔輸送層あるいはスペース層との間には、適宜、電子障壁層を設けてもよい。また、各発光層と電子輸送層との間には、適宜、正孔障壁層を設けてもよい。電子障壁層や正孔障壁層を設けることで、電子又は正孔を発光層内に閉じ込めて、発光層における電荷の再結合確率を高め、発光効率を向上させることができる。
(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もの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、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。
本発明の有機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、特にソーダ石灰ガラス、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ものを挙げられる。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もの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うものであり、4.5eV以上の仕事関数を有するもの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/□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うものであり、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、ホスト材料とドーパント材料を含んでいる。このとき、ホスト材料は、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、ドーパント材料は、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、ホスト材料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材料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り、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、高次構造の相違や、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。
本発明の有機EL素子用材料とそれ以外の化合物を同一の発光層内の燐光ホスト材料として併用してもよいし、複数の発光層がある場合には、そのうちの一つの発光層の燐光ホスト材料として本発明の有機EL素子用材料を用い、別の一つの発光層の燐光ホスト材料として本発明の有機EL素子用材料以外の化合物を用いてもよい。また、本発明の有機EL素子用材料は発光層以外の有機層にも使用しうるものであり、その場合には発光層の燐光ホストとして、本発明の有機EL素子用材料以外の化合物を用いてもよい。
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。)
上記環形成炭素数6~50のアリール基としては、いずれも、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い。
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。
特に、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。
また、式(10)で表されるアントラセン誘導体としては、下記式(10-1)で表されるアントラセン誘導体が好ましい。
R81~R88は、好ましいものも前記同様である。また、R89の好ましいものも、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のアリール基が特に好ましい。
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。)
上記環形成炭素数6~50のアリール基としては、環形成炭素数6~30のアリール基が好ましく、環形成炭素数6~20のアリール基がより好ましく、環形成炭素数6~12のアリール基がさらに好ましく、フェニル基、ナフチル基が特に好ましい。
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、ピレニル基が特に好ましい。
また、ダブルドーパントとしてもよい。発光層において、量子収率の高いドーパント材料を2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。例えば、ホストと赤色ドーパント、緑色のドーパントを共蒸着することによって、黄色の発光層を実現することがある。
さらに、発光層の膜厚は、好ましくは5~50nm、より好ましくは7~50nm、最も好ましくは10~50nmである。5nm未満では発光層形成が困難となり、色度の調整が困難となる恐れがあり、50nmを超えると駆動電圧が上昇する恐れがある。
本発明の有機EL素子は、陰極と発光ユニットとの界面領域に電子供与性ドーパント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。ここで、電子供与性ドーパントとは、仕事関数3.8eV以下の金属を含有するものをいい、その具体例としては、アルカリ金属、アルカリ金属錯体、アルカリ金属化合物、アルカリ土類金属、アルカリ土類金属錯体、アルカリ土類金属化合物、希土類金属、希土類金属錯体、及び希土類金属化合物等から選ばれた少なくとも一種類が挙げられる。
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の割合は、モル比で主成分:電子供与性ドーパント=5:1~1:5であると好ましく、2:1~1:2であるとさらに好ましい。
電子輸送層は、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。電子輸送層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定義することがある。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。本発明の有機EL素子用材料は、電子輸送層に含有される電子輸送材料として用いることもできる。
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の一方は水素原子又は重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または縮合芳香族炭化水素基を表す。Ar1及びAr2の一方は水素原子又は重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。
nは、0~5の整数であり、nが2以上の整数であるとき、複数のR1は互いに同一でも異なっていてもよい。また、隣接する2つのR1同士が互いに結合して、置換もしくは無置換の炭化水素環を形成していてもよい。
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。
但し、Ar1、Ar2のいずれか一方は、置換もしくは無置換の環形成炭素数10~50の縮合芳香族炭化水素環基又は置換もしくは無置換の環形成原子数9~50の縮合芳香族複素環基である。
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、ピローリル基、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、べンゾフリル基、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、トリアゾーリル基、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]ピリミジニル基などが挙げられる。
炭素数1~20のアルキル基としては、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、へキシル基などが挙げられる。
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、ヨウ素およ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、電子輸送層に隣接して設けることができる電子注入層の構成成分として、含窒素環誘導体の他に無機化合物として、絶縁体又は半導体を使用することが好ましい。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。
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ユニットに注入する機能を有する。本発明の有機EL素子用材料は、正孔輸送層に含有される正孔輸送材料として用いることもできる。
正孔輸送層を形成する他の材料としては、芳香族アミン化合物、例えば、下記式(H)で表される芳香族アミン誘導体が好適に用いられる。
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層においては、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。スペース層に用いられる材料としては、上述の正孔輸送層に用いられるものと同様のものが挙げられる。スペース層用の材料として、本発明の有機EL素子用材料を用いることもできる。
本発明の有機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。正孔障壁層用の材料として、本発明の有機EL素子用材料を用いることもできる。
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。
トリプレット障壁層を設ける場合、燐光素子においては、発光層中の燐光発光性ドーパントの三重項エネルギーをETd、トリプレット障壁層として用いる化合物の三重項エネルギーをETTBとすると、ETd<ETTBのエネルギー大小関係であれば、エネルギー関係上、燐光発光性ドーパントの三重項励起子が閉じ込められ(他分子へ移動できなくなり)、該ドーパント上で発光する以外のエネルギー失活経路が断たれ、高効率に発光することができると推測される。ただし、ETd<ETTBの関係が成り立つ場合であってもこのエネルギー差ΔET=ETTB-ETdが小さい場合には、実際の素子駆動環境である室温程度の環境下では、周辺の熱エネルギーにより吸熱的にこのエネルギー差ΔETを乗り越えて三重項励起子が他分子へ移動することが可能であると考えられる。特に燐光発光の場合は蛍光発光に比べて励起子寿命が長いため、相対的に吸熱的励起子移動過程の影響が現れやすくなる。室温の熱エネルギーに対してこのエネルギー差ΔETは大きい程好ましく、0.1eV以上であるとさらに好ましく、0.2eV以上であると特に好ましい。一方、蛍光素子においては、国際公開WO2010/134350A1に記載するTTF素子構成のトリプレット障壁層用の材料として、本発明の有機EL素子用材料を用いることもできる。
電子注入層の電子移動度は、電界強度0.04~0.5MV/cmの範囲において、10-6cm2/Vs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。
実施例1(化合物1の合成)
アルゴン雰囲気下、3-ブロモフルオランテン7.0g、2-クロロアニリン4.76g、トリスジベンジリデンアセトンジパラジウム(0)0.46g、トリ-t-ブチルホスフィンテトラフルオロハイドロボレート0.58g、ナトリウム-t-ブトキシド3.4g、脱水トルエン200mLをフラスコに仕込み、80℃で8時間加熱撹拌した。室温まで冷却した後、反応溶液をトルエンで抽出し、セライトろ過した。ろ液を濃縮し、残渣をシリカゲルカラムクロマトグラフィで精製し、3-(2-クロロアニリノ)フルオランテン6.14gを得た。(収率75%)
アルゴン雰囲気下、3-(2-クロロアニリノ)フルオランテン6.14g、酢酸パラジウム0.13g、炭酸カリウム5.18g、トリシクロヘキシルホスフィンテトラフルオロハイドロボレート0.41g、N,N-ジメチルアセトアミド40mLをフラスコに仕込み、140℃で24時間加熱撹拌した。室温まで冷却後、トルエンを用いて抽出し、不溶物をろ別した。ろ液を濃縮し、残渣をシリカゲルカラムクロマトグラフィで精製し、化合物1 1.87gを得た。(収率34%)
WO2010/123153記載の方法で合成した2-ブロモ-3-フルオランテンアミン29.6g、ヨウ化カリウム0.83gにアセトニトリル300mLを加え、室温にて撹拌し、t-ブチルヒドロパーオキシドの70質量%水溶液50gを滴下した。反応溶液を80℃にて15時間加熱撹拌を続けた。反応終了後、室温まで冷却後、飽和チオ硫酸ナトリウム水溶液でクエンチした。反応溶液をトルエンを用いて抽出し、水層を除去した。有機層を硫酸マグネシウムで乾燥させた後、溶媒を減圧留去した。残渣をシリカゲルカラムクロマトグラフィにて精製し、2-ブロモ-3-ニトロフルオランテン14.7gを得た。
(2)2-(1-ナフチル)-3-ニトロフルオランテンの合成
アルゴン雰囲気下1-ナフタレンボロン酸8.53g、2-ブロモ-3-ニトロフルオランテン14.7g、テトラキストリフェニルホスフィンパラジウム(0)1.04g、1,2-ジメトキシエタン70mL、トルエン70mL、2M炭酸ナトリウム水溶液70mLをフラスコに仕込み、8時間加熱還流攪拌した。室温まで冷却後、反応溶液をトルエンを用いて抽出し、水層を除去した後、有機層を飽和食塩水で洗浄した。有機層を硫酸マグネシウムで乾燥させた後、濃縮し、残渣をシリカゲルカラムクロマトグラフィで精製し2-(1-ナフチル)-3-ニトロフルオランテン10.4gを得た。
(3)中間体(G)の合成
アルゴン雰囲気下、2-(1-ナフチル)-3-ニトロフルオランテン10.4g、トリフェニルホスフィン18.3g、o-ジクロロベンゼン400mLを仕込み、48時間加熱還流撹拌した。室温まで冷却後、ヘキサン1Lを加え析出した結晶をろ取した。得られた個体をトルエンで再結晶し、中間体(G)3.95gを得た。
(4)化合物28の合成
化合物2の合成において、化合物1の代わりに中間体(G)を、中間体(B)の代わりに2-クロロ-4-フェニルキナゾリンを用いて同様の方法で合成した。このものは、マススペクトル分析の結果、目的物であり、分子量545.19に対し、m/e=545であった。
25mm×75mm×厚さ1.1mmのITO透明電極付きガラス基板(ジオマテック株式会社製)をイソプロピルアルコール中で超音波洗浄を5分間行なった後、UVオゾン洗浄を30分間行った。
洗浄後の130nm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第1正孔輸送材料として下記化合物HT-1を蒸着し、膜厚45nmの第1正孔輸送層を成膜した。第1正孔輸送層の成膜に続けて、第2正孔輸送材料として下記化合物HT-2を蒸着し、膜厚10nmの第2正孔輸送層を成膜した。
さらに、この第2正孔輸送層上に、ホスト材料として前記実施例2で得た化合物2と、燐光発光材料として下記化合物RD-1とを共蒸着し、膜厚40nmの燐光発光層を成膜した。発光層内における化合物RD-1の濃度は5.0質量%であった。この共蒸着膜は発光層として機能する。
そして、この発光層成膜に続けて下記化合物ET-1を膜厚40nmで成膜した。この化合物ET-1膜は第1電子輸送層として機能する。
次に、LiFを電子注入性電極(陰極)として成膜速度0.01nm/secで成膜し、膜厚を1nmとした。このLiF膜上に金属Alを蒸着させ、金属陰極を膜厚80nmで形成し有機EL素子を作製した。
以下に、実施例50および比較例1で使用した化合物を示す。
得られた有機EL素子の室温及びDC定電流駆動(電流密度10mA/cm2)での外部量子効率を輝度計(ミノルタ社製分光輝度放射計CS-1000)を用いて測定した結果を表1及び表2に示す。
三重項エネルギー(EgT)は、以下の方法により求めた。
各化合物を、公知の燐光測定法(例えば、「光化学の世界」(日本化学会編,1993)50頁付近の記載の方法)により測定した。具体的には、各化合物を溶媒に溶解(試料10[μmol/リットル]、EPA(ジエチルエーテル:イソペンタン:エタノール=5:5:5(容積比)、各溶媒は分光用グレード)し、燐光測定用試料とした。石英セルへ入れた燐光測定用試料を77[K]に冷却し、励起光を燐光測定用試料に照射し、波長を変えながら燐光強度を測定した。燐光スペクトルは、縦軸を燐光強度、横軸を波長とした。
この燐光スペクトルの短波長側の立ち上がりに対して接線を引き、その接線と横軸との交点の波長値λedge[nm]を求めた。この波長値を次に示す換算式でエネルギー値に換算した値をEgTとした。
換算式:EgT[eV]=1239.85/λedge
燐光スペクトルの短波長側の立ち上がりに対する接線は以下のように引いた。燐光スペクトルの短波長側から、スペクトルの極大値のうち、最も短波長側の極大値までスペクトル曲線上を移動する際に、長波長側に向けて曲線上の各点における接線を考える。この接線は、曲線が立ち上がるにつれ(つまり縦軸が増加するにつれ)、傾きが増加する。この傾きの値が極大値をとる点において引いた接線が、当該燐光スペクトルの短波長側の立ち上がりに対する接線とした。
なお、スペクトルの最大ピーク強度の10%以下のピーク強度をもつ極大点は、上述の最も短波長側の極大値には含めず、最も短波長側の極大値に最も近い、傾きの値が極大値をとる点において引いた接線を当該燐光スペクトルの短波長側の立ち上がりに対する接線とする。
燐光の測定には、(株)日立ハイテクノロジー製のF-4500形分光蛍光光度計本体と低温測定用オプション備品を用いた。なお、測定装置はこの限りではなく、冷却装置及び低温用容器と、励起光源と、受光装置とを組み合わせることにより、測定してもよい。
実施例50において、発光層のホスト材料として化合物2を用いる代わりに比較化合物1を用いて発光層を形成した以外は実施例50と同様にして有機EL素子を作製した。有機EL素子の外部量子効率の測定結果と、比較化合物1の三重項エネルギーの測定結果を表1に示す。
さらに、本発明の縮環フルオランテン誘導体である化合物2は、比較化合物1の縮環様式と比較して、N上の置換基と縮合フルオランテン母骨格とのねじれが大きく、ほぼ直角になる。このことにより、化合物2を発光層のホスト材料として用いた実施例1の素子では、ホスト分子自体の立体排除性が増すため、ホスト分子中に数%の割合で含有されるドーパント同士の会合による濃度消光が防止され、高効率化に寄与している効果もあると考えられる。
実施例50で用いた洗浄後の130nm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正孔注入材料として下記化合物HA-1を蒸着し、膜厚10nmの正孔注入層を成膜した。正孔注入層の成膜に続けて、第1正孔輸送材料として下記化合物HT-3を蒸着し、膜厚20nmの第1正孔輸送層を成膜した。第1正孔輸送層の成膜に続けて、第2正孔輸送材料として下記化合物HT-4を蒸着し、膜厚10nmの第2正孔輸送層を成膜した。
さらに、この第2正孔輸送層上に、ホスト材料として前記実施例10で得た化合物10と、燐光発光材料として下記化合物RD-1とを共蒸着し、膜厚40nmの燐光発光層を成膜した。発光層内における化合物RD-1の濃度は5.0質量%であった。この共蒸着膜は発光層として機能する。
そして、この発光層成膜に続けて下記化合物ET-1を膜厚45nmで成膜した。この化合物ET-1膜は第1電子輸送層として機能する。
次に、LiFを電子注入性電極(陰極)として成膜速度0.01nm/secで成膜し、膜厚を1nmとした。このLiF膜上に金属Alを蒸着させ、金属陰極を膜厚80nmで形成し有機EL素子を作製した。
以下に、実施例51~58および比較例2、3で使用した化合物を示す。
実施例51において、化合物10を用いる代わりに表2に記載した化合物を用いた以外は実施例51と同様にして素子を作製し、評価を実施した。結果を表2に示す。
実施例51において、発光層のホスト材料として化合物10を用いる代わりに比較化合物2、3を用いて発光層を形成した以外は実施例51と同様にして有機EL素子を作製し、
評価を実施した。結果を表2に示す。
2 基板
3 陽極
4 陰極
5 発光層
6 陽極側有機薄膜層
7 陰極側有機薄膜層
10 有機薄膜層
Claims (18)
- 下記一般式(c)で表されることを特徴とする請求項1に記載の縮合フルオランテン化合物。
R1c~R15cは、それぞれ独立に、水素原子、置換基又はLcとの結合手を示し、R1c~R15cのうち隣接する置換基同士は、互いに結合して飽和または不飽和の環構造を形成してもよい。
Ycは、置換もしくは無置換の環形成炭素数6~60のp価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3~60のp価の複素環基を示す。
Lcは、単結合または、置換もしくは無置換の環形成炭素数6~60の2価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3~60の2価の複素環基、または、置換もしくは無置換の炭素数1~50のアルキレン基を示す。
pは、1~6の整数を示す。] - 前記一般式(a)におけるR1a~R15a、前記(b)におけるR1b~R15b、前記(c)におけるR1c~R15c及び前記一般式(d)におけるR1d~R15dのうち少なくとも1つが置換もしくは無置換の環形成炭素数6~60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3~60の複素環基である請求項1~4いずれかに記載の縮合フルオランテン化合物。
- 前記一般式(a)におけるXaがN(R15a)を示し、前記一般式(b)におけるXbがN(R15b)を示し、前記一般式(c)におけるXcがN(R15c)を示し、前記一般式(d)におけるXdがN(R15d)を示す請求項1~5のいずれかに記載の縮合フルオランテン化合物。
- 前記一般式(a)におけるR15a、前記一般式(b)におけるR15b、前記一般式(c)におけるR15c及び前記一般式(d)におけるR15dが、置換もしくは無置換の環形成炭素数6~60の芳香族炭化水素基を示す請求項6に記載の縮合フルオランテン化合物。
- 前記一般式(a)におけるR15a、前記一般式(b)におけるR15b、前記一般式(c)におけるR15c及び前記一般式(d)におけるR15dが、置換もしくは無置換の2環以上が縮環してなる環形成炭素数10~60の縮合芳香族炭化水素基である請求項7に記載の縮合フルオランテン化合物。
- 前記一般式(a)におけるR15a、前記一般式(b)におけるR15b、前記一般式(c)におけるR15c及び前記一般式(d)におけるR15dが、置換もしくは無置換の環形成原子数3~60の複素環基である請求項6に記載の縮合フルオランテン化合物。
- 請求項1~9のいずれかに記載の縮合フルオランテン化合物を含有する有機エレクトロルミネッセンス素子用材料。
- 陰極と陽極間に少なくとも発光層を含む一層又は複数層からなる有機薄膜層が挟持されている有機エレクトロルミネッセンス素子において、該有機薄膜層の少なくとも1層が、請求項1~9のいずれかに記載の縮合フルオランテン化合物を含有する有機エレクトロルミネッセンス素子。
- 前記発光層が前記縮合フルオランテン化合物を含有する請求項11に記載の有機エレクトロルミネッセンス素子。
- 前記陽極と前記発光層との間に、さらに陽極側有機薄膜層を有し、該陽極側有機薄膜層が前記縮合フルオランテン化合物を含有する請求項11又は12に記載の有機エレクトロルミネッセンス素子。
- 前記陰極と前記発光層との間に、さらに陰極側有機薄膜層を有し、該陰極側有機薄膜層が前記縮合フルオランテン化合物を含有する請求項11~13のいずれかに記載の有機エレクトロルミネッセンス素子。
- 前記発光層が燐光発光材料を含有する請求項11~14のいずれかに記載の有機エレクトロルミネッセンス素子。
- 前記発光層が蛍光発光材料を含有する請求項11~14のいずれかに記載の有機エレクトロルミネッセンス素子。
- 前記燐光発光材料が、イリジウム(Ir)、オスミウム(Os)、白金(Pt)から選択される金属原子のオルトメタル化錯体である請求項15に記載の有機エレクトロルミネッセンス素子。
- 請求項11~17のいずれか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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US20160322587A1 (en) | 2016-11-03 |
KR20150108813A (ko) | 2015-09-30 |
JP5802854B2 (ja) | 2015-11-04 |
KR101645145B1 (ko) | 2016-08-02 |
US9741943B2 (en) | 2017-08-22 |
CN104768928A (zh) | 2015-07-08 |
JPWO2014157574A1 (ja) | 2017-02-16 |
KR101838833B1 (ko) | 2018-04-26 |
CN104768928B (zh) | 2018-06-08 |
JP2015180643A (ja) | 2015-10-15 |
JP5802862B2 (ja) | 2015-11-04 |
KR20160092059A (ko) | 2016-08-03 |
US9419226B2 (en) | 2016-08-16 |
US20150228904A1 (en) | 2015-08-13 |
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