WO2016042781A1 - 新規な化合物 - Google Patents
新規な化合物 Download PDFInfo
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- WO2016042781A1 WO2016042781A1 PCT/JP2015/004810 JP2015004810W WO2016042781A1 WO 2016042781 A1 WO2016042781 A1 WO 2016042781A1 JP 2015004810 W JP2015004810 W JP 2015004810W WO 2016042781 A1 WO2016042781 A1 WO 2016042781A1
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- substituted
- unsubstituted
- carbon atoms
- ring
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 126
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 59
- 125000003118 aryl group Chemical group 0.000 claims abstract description 47
- 125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
- 125000005843 halogen group Chemical group 0.000 claims abstract description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 213
- -1 benzoanthryl group Chemical group 0.000 claims description 69
- 238000005401 electroluminescence Methods 0.000 claims description 60
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 239000000463 material Substances 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 125000006413 ring segment Chemical group 0.000 claims description 35
- 125000002950 monocyclic group Chemical group 0.000 claims description 27
- 125000004429 atom Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000005104 aryl silyl group Chemical group 0.000 claims description 21
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 19
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- 125000001769 aryl amino group Chemical group 0.000 claims description 15
- 125000005110 aryl thio group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 239000002019 doping agent Substances 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 125000005561 phenanthryl group Chemical group 0.000 claims description 10
- 239000010409 thin film Substances 0.000 claims description 10
- 150000001721 carbon Chemical class 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 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 claims description 2
- 239000010410 layer Substances 0.000 description 93
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000010408 film Substances 0.000 description 38
- 238000002347 injection Methods 0.000 description 33
- 239000007924 injection Substances 0.000 description 33
- 239000000243 solution Substances 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- 150000001454 anthracenes Chemical class 0.000 description 19
- 238000010898 silica gel chromatography Methods 0.000 description 18
- 239000012300 argon atmosphere Substances 0.000 description 17
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 16
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- 239000000758 substrate Substances 0.000 description 13
- 230000005525 hole transport Effects 0.000 description 12
- 230000032258 transport Effects 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- 238000001819 mass spectrum Methods 0.000 description 8
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalene Chemical compound C1=CC=C2C(C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 7
- 229940125904 compound 1 Drugs 0.000 description 7
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 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 6
- NNVZVNMCMRPEND-UHFFFAOYSA-N 1,6-dibromo-3,8-di(propan-2-yl)pyrene Chemical compound C1=C2C(C(C)C)=CC(Br)=C(C=C3)C2=C2C3=C(C(C)C)C=C(Br)C2=C1 NNVZVNMCMRPEND-UHFFFAOYSA-N 0.000 description 5
- MLQRWBAGMZFMGH-UHFFFAOYSA-N 2-methyl-N-(2-methylphenyl)-5-phenylaniline Chemical compound CC1=C(NC2=C(C=CC=C2)C)C=C(C=C1)C1=CC=CC=C1 MLQRWBAGMZFMGH-UHFFFAOYSA-N 0.000 description 5
- 239000000956 alloy Substances 0.000 description 5
- 229910045601 alloy Inorganic materials 0.000 description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 5
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 5
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- YLKSTPDTTKOSIL-UHFFFAOYSA-N 2-methyl-5-phenylaniline Chemical compound C1=C(N)C(C)=CC=C1C1=CC=CC=C1 YLKSTPDTTKOSIL-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 4
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- JRCJYPMNBNNCFE-UHFFFAOYSA-N 1,6-dibromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=C(Br)C=CC2=C1 JRCJYPMNBNNCFE-UHFFFAOYSA-N 0.000 description 3
- BVTFEWBUBJTNHZ-UHFFFAOYSA-N 2-bromo-1-methyl-4-phenylbenzene Chemical compound C1=C(Br)C(C)=CC=C1C1=CC=CC=C1 BVTFEWBUBJTNHZ-UHFFFAOYSA-N 0.000 description 3
- ANRAKTDEUFLKDO-UHFFFAOYSA-N 2-bromo-4-iodo-1-methylbenzene Chemical compound CC1=CC=C(I)C=C1Br ANRAKTDEUFLKDO-UHFFFAOYSA-N 0.000 description 3
- JONFSRMLMYTWFM-UHFFFAOYSA-N 2-iodo-1-methyl-4-phenylbenzene Chemical group C1=C(I)C(C)=CC=C1C1=CC=CC=C1 JONFSRMLMYTWFM-UHFFFAOYSA-N 0.000 description 3
- WJGUWCMVSYFLDU-UHFFFAOYSA-N 4-fluoro-2-phenylbenzonitrile Chemical compound FC1=CC=C(C#N)C(C=2C=CC=CC=2)=C1 WJGUWCMVSYFLDU-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004076 pyridyl group Chemical group 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CGQUEXVYVHPDFT-UHFFFAOYSA-N 3-(2-methyl-5-phenylanilino)benzonitrile Chemical compound CC1=C(NC=2C=C(C#N)C=CC=2)C=C(C=C1)C1=CC=CC=C1 CGQUEXVYVHPDFT-UHFFFAOYSA-N 0.000 description 2
- XXHWJEPLAQOVFF-UHFFFAOYSA-N 4-methyl-3-(2-methyl-5-phenylanilino)benzonitrile Chemical compound CC1=C(C=C(C#N)C=C1)NC1=C(C=CC(=C1)C1=CC=CC=C1)C XXHWJEPLAQOVFF-UHFFFAOYSA-N 0.000 description 2
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 2
- 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 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- AZWHFTKIBIQKCA-UHFFFAOYSA-N [Sn+2]=O.[O-2].[In+3] Chemical compound [Sn+2]=O.[O-2].[In+3] AZWHFTKIBIQKCA-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- 150000001717 carbocyclic compounds Chemical class 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 2
- 229910001947 lithium oxide Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 2
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- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- OYQCBJZGELKKPM-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O-2].[Zn+2].[O-2].[In+3] OYQCBJZGELKKPM-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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Definitions
- the present invention relates to a novel compound and an organic electroluminescence device using the same.
- Organic electroluminescence (EL) elements are promising for use as solid-state, inexpensive, large-area full-color display elements, and many developments have been made.
- an organic EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the layer. When an electric field is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side. Further, the electrons recombine with holes in the light emitting layer to generate an excited state, and energy is emitted as light when the excited state returns to the ground state.
- An object of the present invention is to provide a compound capable of producing an organic EL device having excellent luminous efficiency.
- a compound represented by the following formula (1) Ar is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, Each R a is a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms or a substituted or unsubstituted cyclic alkyl group having 3 to 15 carbon atoms; R b1 to R b4 are each a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted cyclic alkyl group having 3 to 15 carbon atoms, a substituted or unsubstituted carbon, An alkylsilyl group having 1 to 45 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, a substituted
- the plurality of R b1 When x is an integer of 2 or more, the plurality of R b1 may be the same or different, and when y is an integer of 2 or more, the plurality of R b2 may be the same or different, and z is When it is an integer of 2 or more, the plurality of R b3 or R b4 may be the same or different. )
- a compound capable of producing an organic EL device having excellent luminous efficiency can be provided.
- Ar is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
- R a is a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms or a substituted or unsubstituted cyclic alkyl group having 3 to 15 carbon atoms.
- R b1 to R b4 are each a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted cyclic alkyl group having 3 to 15 carbon atoms, a substituted or unsubstituted carbon, An alkylsilyl group having 1 to 45 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 15 carbon atoms, a substituted or unsubstituted ring forming carbon atom having 6 to 30 carbon atoms Aryloxy group, substituted or unsubstituted alkylthio group having 1 to 15 carbon atoms, substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, substituted or unsubstituted arylamino group
- R c1 to R c10 are each a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted cyclic alkyl group having 3 to 15 carbon atoms, a substituted or unsubstituted group.
- x is an integer from 0 to 3
- y is an integer from 0 to 4
- z is an integer from 0 to 5, respectively.
- x is an integer of 2 or more
- the plurality of R b1 may be the same or different
- y is an integer of 2 or more
- the plurality of R b2 may be the same or different
- z is When it is an integer of 2 or more, the plurality of R b3 or R b4 may be the same or different.
- the compound according to one embodiment of the present invention can exhibit excellent luminous efficiency when used in an organic EL device by having the above specific structure.
- the above compound is preferably represented by the following formula (2).
- Ar, R a , R b1 to R b4 , R c1 to R c10 , x, z, and * are the same as those in the formula (1).
- R c1 to R c10 are groups other than arylamino groups, that is, a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted carbon number of 3;
- Substituted or unsubstituted aryloxy groups having 6 to 30 ring carbon atoms substituted or unsubstituted alkylthio groups having 1 to 15 carbon atoms, substituted or unsubstituted arylthio groups having 6 to 30 ring carbon atoms, substituted or Bonded to an unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 ring atoms, or a nitrogen atom
- the compound is a disubstituted product of an arylamino group.
- the above compound is preferably represented by the following formula (3), more preferably represented by the following formula (4).
- Ar, R a , R b1 to R b4 , R c2 to R c10 , x, z, and * are the same as those in the formula (1).
- R c2 to R c5 and R c7 to R c10 are each a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, or a substituted or unsubstituted cyclic group having 3 to 15 carbon atoms.
- Alkyl group substituted or unsubstituted alkylsilyl group having 1 to 45 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 15 carbon atoms, substituted or unsubstituted Substituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 15 carbon atoms, substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, substituted or unsubstituted ring An arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring atom number of 3 to 3 30 heteroaryl groups.
- R c2 , R c4 to R c10 are each a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted cyclic alkyl group having 3 to 15 carbon atoms, Substituted or unsubstituted alkylsilyl group having 1 to 45 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 15 carbon atoms, substituted or unsubstituted ring Aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthio
- R c7 is preferably a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms or a substituted or unsubstituted cyclic alkyl group having 3 to 15 carbon atoms.
- the benzene ring-containing group to which R b1 is bonded and the benzene ring-containing group to which R b2 are bonded do not have a substituent at the para position relative to the bonding position with the N atom (that is, a hydrogen atom is bonded).
- a substituent at the para position relative to the bonding position with the N atom that is, a hydrogen atom is bonded.
- R b2 is bonded to R b2 is preferably not bonded to the para position with respect to the bonding position with the N atom.
- the emission wavelength is increased by having an alkyl group or an aryl group at this position, and the blue chromaticity of the obtained light emission is reduced. There is a risk.
- this position does not have an alkyl group or an aryl group. The above description does not prevent Rb1 and Ar from being substituted at the para position, and these may be substituted at the para position.
- Ar is preferably bonded to the para position relative to Ra.
- a benzene ring-containing group R b1 is attached is represented by the following formula (10)
- a benzene ring-containing group R b2 are bonded is represented by the following formula (11).
- the molecular arrangement of the compound according to one embodiment of the present invention in the organic film is optimized, and energy transfer from the light emitting layer when used as the light emitting layer dopant material of the organic EL element. It is considered that more efficient light emission can be realized by optimizing the above.
- Ar, R a , R b1 , R b2 and x are the same as those in the formula (1).
- R b3 and R b4 are preferably not bonded to the para position with respect to the bonding position with the N atom. That is, it is preferably bonded to the meta position or the ortho position with respect to the bonding position with the N atom, and preferably bonded to the ortho position.
- the benzene ring-containing group to which R b3 is bonded is preferably represented by the following formula (12)
- the benzene ring-containing group to which R b4 is bonded is preferably represented by the following formula (13).
- R b3 and R b4 are the same as those in formula (1).
- R b3 ′ and R b4 ′ are each a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms or a substituted or unsubstituted cyclic alkyl group having 3 to 15 carbon atoms, z1 is an integer of 0 to 4, respectively.
- R a is preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.
- R b1 to R b4 are preferably groups other than electron-withdrawing groups, specifically, substituted or unsubstituted alkyl groups having 1 to 15 carbon atoms, substituted or unsubstituted C 3 to 15 carbon atoms, respectively.
- a heteroaryl group Preferably a heteroary
- R b1 to R b4 are each a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted cyclic alkyl group having 3 to 15 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 45 carbon atoms. It is more preferably an alkylsilyl group, a substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
- R c1 to R c10 are a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted cyclic alkyl group having 3 to 15 carbon atoms, and a substituted or unsubstituted alkylsilyl group having 1 to 45 carbon atoms.
- a substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms is preferred, and a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms and a substituted or unsubstituted cyclic alkyl group having 3 to 15 carbon atoms are more preferred.
- the compound according to one embodiment of the present invention is preferably a compound represented by any of the following formulas.
- Each group in the formulas (4-2) and (5-2) is as described above.
- the above compounds can be produced by the methods described in the examples. Furthermore, following this reaction, the compound of the present invention can be synthesized by using known alternative reactions and raw materials that match the target product.
- the hydrogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (protium), deuterium (deuterium), and tritium.
- the number of ring-forming carbon atoms refers to an atom constituting 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 bridging compound, a carbocyclic compound, or a heterocyclic compound). Of carbon atoms. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbons.
- the “ring-forming carbon number” described below is the same unless otherwise specified.
- the benzene ring has 6 ring carbon atoms
- the naphthalene ring has 10 ring carbon atoms
- the pyridinyl group has 5 ring carbon atoms
- the furanyl group has 4 ring carbon atoms.
- the carbon number of the alkyl group is not included in the number of ring-forming carbons.
- the carbon number of the fluorene ring as a substituent is not included in the number of ring-forming carbons.
- the number of ring-forming atoms means a compound (for example, a monocyclic compound, a condensed ring compound, a bridging compound, a carbocyclic compound, or a heterocyclic ring) having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic ring, a condensed ring, or a ring assembly). Represents the number of atoms constituting the ring of the compound).
- An atom that does not constitute a ring for example, a hydrogen atom that terminates a bond of an atom that constitutes a ring
- an atom contained in a substituent when the ring is substituted by a substituent is not included in the number of ring-forming atoms.
- the “number of ring-forming atoms” described below is the same unless otherwise specified.
- the pyridine ring has 6 ring atoms
- the quinazoline ring has 10 ring atoms
- the furan ring has 5 ring atoms.
- a hydrogen atom bonded to a carbon atom of a pyridine ring or a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms. Further, when, for example, a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the number of atoms of the fluorene ring as a substituent is not included in the number of ring-forming atoms.
- the “carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY” represents the number of carbon atoms in the case where the ZZ group is unsubstituted and substituted. In this case, the number of carbon atoms in the substituent is not included.
- “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
- atom number XX to YY in the expression “a ZZ group having a substituted or unsubstituted atom number XX to YY” represents the number of atoms when the ZZ group is unsubstituted and substituted. 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 means that a hydrogen atom is bonded without being substituted with the above substituent.
- alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, An n-octyl group and the like can be mentioned.
- the alkyl group preferably has 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms.
- methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl and n-hexyl are preferred.
- cyclic alkyl group examples include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, adamantyl group, norbornyl group and the like.
- the number of ring-forming carbon atoms is preferably 3 to 10, more preferably 3 to 8, and still more preferably 5 to 8. Also, it may be 3-6.
- aryl group for example, phenyl group, naphthyl group, anthryl group, phenanthryl group, naphthacenyl group, pyrenyl group, chrysenyl group, benzo [c] phenanthryl group, benzo [g] chrycenyl group, triphenylenyl group, fluorenyl group, benzofuryl group
- aryl group preferably has 6 to 20 ring carbon atoms, more preferably 6 to 12, and among the aryl groups described above, a phenyl group and a biphenyl group are particularly preferable.
- the alkylsilyl group is represented by —SiY 3, and examples of Y include the above examples of alkyl.
- examples of the alkylsilyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, and a triisopropylsilyl group.
- the arylsilyl group is a silyl group substituted with 1 to 3 aryl groups, and examples of the aryl group include the above examples of aryl. In addition to the aryl group, the above alkyl group may be substituted. Examples of the arylsilyl group include a triphenylsilyl group and a phenyldimethylsilyl group.
- the alkoxy group is represented as —OY, and examples of Y include the above alkyl examples.
- the alkoxy group is, for example, a methoxy group or an ethoxy group.
- the aryloxy group is represented by —OZ, and examples of Z include the above aryl groups.
- the aryloxy group is, for example, a phenoxy group.
- the alkylthio group is represented by —SY, and examples of Y include the above alkyl examples.
- the arylthio group is represented by —SZ, and examples of Z include the above examples of aryl groups.
- the arylamino group is represented as —NZ 2, and examples of Z include the examples of the aryl group described above.
- heteroaryl groups include pyrrolyl, triazinyl, pyrazinyl, pyrimidinyl, pyridinyl, indolyl, isoindolyl, imidazolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, dibenzofuran, Thiophenyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, phenothiazinyl group, phenoxazinyl group, oxazolyl group, oxadiazolyl group, flazanyl group, A thienyl group, a benzothiophenyl group, etc. are mentioned.
- the number of ring-forming atoms of the heteroaryl group is preferably 5-20, and more preferably 5-14.
- the heteroaryl group is preferably a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group, more preferably a 1-dibenzofuranyl group, a 2-dibenzofuranyl group, a 3-dibenzofuranyl group, 4 -Dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group, 4-dibenzothiophenyl group.
- X and Y are each an oxygen atom, a sulfur atom, a nitrogen atom or a —NH— group.
- halogen atom examples include fluorine, chlorine, bromine, iodine, and the like, preferably a fluorine atom.
- substituents may be further substituted with the above substituents.
- a plurality of these substituents may be bonded to each other to form a ring.
- the above-mentioned compound can be used as an organic electroluminescence (EL) element material, preferably an organic EL element issuance material, more preferably a dopant (dopant material).
- EL organic electroluminescence
- one or more organic thin film layers including at least a light emitting layer are sandwiched between a cathode and an anode, and at least one of the organic thin film layers is represented by the above formula (1).
- a light emitting layer contains the above compound.
- a light emitting layer can be comprised only from the said compound, or can also be contained as a host or a dopant.
- the organic EL device preferably includes at least one organic thin film layer, the above compound, an anthracene derivative represented by the following formula (5), or pyrene represented by the following formula (6). Containing at least one derivative.
- the light emitting layer contains the above compound as a dopant and an anthracene derivative as a host.
- the anthracene derivative represented by the formula (5) is the following compound.
- Ar 11 and Ar 12 are each independently a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms or a substituted or unsubstituted condensed ring having 8 to 50 ring atoms. Or a group composed of a combination of a monocyclic group and a condensed ring group.
- R 101 to R 108 are each independently a hydrogen atom, a single atom of 5 to 50 (preferably 5 to 30, more preferably 5 to 20, more preferably 5 to 12) ring-substituted or unsubstituted ring-forming atoms.
- R 101 ⁇ R 108 is a hydrogen atom, or one of R 101 and R 108, one of R 104 and R 106, both of R 101 and R 106, or both by R 108 and R 104 is, Monocyclic group having 5 to 50 ring atoms (preferably phenyl group, biphenylyl group, terphenylyl group), substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably methyl group, ethyl group, n- A group selected from the group consisting of a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group) and a substituted silyl group (preferably a trimethylsilyl group). More preferably, all of 101 to R 108 are hydrogen atoms.
- the monocyclic group in the formula (5) is a group composed only of a ring structure having no fused ring structure.
- Specific examples of the monocyclic group having 5 to 50 ring atoms include aromatic groups such as phenyl group, biphenylyl group, terphenylyl group, quarterphenylyl group, pyridyl group, pyrazyl group, pyrimidyl group, triazinyl group, furyl group.
- heterocyclic groups such as a thienyl group are preferred.
- a phenyl group, a biphenylyl group, and a terphenylyl group are preferable.
- the condensed ring group is a group in which two or more ring structures are condensed.
- the condensed ring group having 8 to 50 ring atoms include naphthyl group, phenanthryl group, anthryl group, chrysenyl group, benzoanthryl group, benzophenanthryl group, triphenylenyl group, benzocrisenyl group, indenyl group, fluorenyl Group, benzofluorenyl group, dibenzofluorenyl group, fluoranthenyl group, benzofluoranthenyl group and other condensed aromatic ring groups, benzofuranyl group, benzothiophenyl group, indolyl group, dibenzofuranyl group, dibenzo A condensed heterocyclic group such as a thiophenyl group, a carbazolyl group, a quinolyl group, or a phenanthrolinyl group is preferred.
- the fluorenyl group may have one or two substituents at the 9-position, and examples of the substituent include an alkyl group, an aryl group, an alkylsilyl group, an arylsilyl group, and an alkoxy group. . Specific examples of such a fluorenyl group include a 9,9-dimethylfluorenyl group and a 9,9-diphenylfluorenyl group.
- a fluorenyl group when it is described as a fluorenyl group, it may have the same substituent unless otherwise specified.
- Examples of the condensed ring group include naphthyl group, phenanthryl group, anthryl group, fluorenyl group (specifically, 9,9-dimethylfluorenyl group, etc.), fluoranthenyl group, benzoanthryl group, dibenzothiol.
- a phenyl group, a dibenzofuranyl group, and a carbazolyl group are preferable.
- an alkyl group, a cycloalkyl group (cyclic alkyl group), an alkoxy group, an alkyl part and an aryl part of an aralkyl group, an aryloxy group, a substituted silyl group (an alkylsilyl group, an arylsilyl group), a halogen atom Specific examples are the same as the specific examples of each group in the above-described formula (1) and substituents in “substituted or unsubstituted...”.
- the aralkyl group is represented by —Y—Z.
- Y include alkylene examples corresponding to the above alkyl examples, and examples of Z include the above aryl examples.
- the aralkyl group has 7 to 50 carbon atoms (the aryl moiety has 6 to 49 carbon atoms (preferably 6 to 30, more preferably 6 to 20, particularly preferably 6 to 12), and the alkyl moiety has 1 to 44 carbon atoms. (Preferably 1-30, more preferably 1-20, still more preferably 1-10, particularly preferably 1-6)), for example, benzyl group, phenylethyl group, 2-phenylpropane-2- It is an yl group.
- substituents of “substituted or unsubstituted” for Ar 11 , Ar 12 , R 1 to R 8 monocyclic groups, condensed ring groups, alkyl groups, cycloalkyl groups, silyl groups, alkoxy groups, cyano groups, halogen atoms (Especially fluorine) is preferable, particularly preferably a monocyclic group or a condensed ring group, and preferable specific substituents are as described above.
- the above-mentioned monocyclic group or condensed ring group is preferable as the substituent for Ar 11 and Ar 12 .
- the anthracene derivative represented by the formula (5) is preferably any of the following anthracene derivatives (A), (B), and (C), and is selected depending on the configuration of the organic EL element to be applied and the required characteristics.
- Anthracene derivatives which are substituted or unsubstituted fused ring groups in which Ar 11 and Ar 12 in formula (5) are different (including the difference in the position to which the anthracene ring is bonded) are particularly preferred, and preferred specific examples of the fused ring are as described above. It is. Of these, a naphthyl group, a phenanthryl group, a benzanthryl group, a fluorenyl group (specifically, 9,9-dimethylfluorenyl group, etc.) and a dibenzofuranyl group are preferable.
- Anthracene derivative (B) In the anthracene derivative (B), one of Ar 11 and Ar 12 in formula (5) is a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, and the other of Ar 11 and Ar 12 is substituted or unsubstituted. A substituted condensed ring group having 8 to 50 ring-forming atoms.
- Ar 12 is a naphthyl group, phenanthryl group, benzoanthryl group, fluorenyl group (specifically, 9,9-dimethylfluorenyl group, etc.), or dibenzofuranyl group
- Ar 11 is an unsubstituted phenyl group, a monocyclic group or a condensed ring group (for example, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group (specifically, 9,9-dimethylfluorene group).
- anthracene derivative (B) is a derivative in which Ar 12 is a substituted or unsubstituted condensed ring group having 8 to 50 ring-forming atoms and Ar 11 is an unsubstituted phenyl group.
- the condensed ring group is particularly preferably a phenanthryl group, a fluorenyl group (specifically, 9,9-dimethylfluorenyl group, etc.), a dibenzofuranyl group, or a benzoanthryl group.
- Anthracene derivative (C) In the anthracene derivative (C), Ar 11 and Ar 12 in the formula (5) are each independently a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms.
- a preferred form of the anthracene derivative (C) includes a derivative in which both Ar 11 and Ar 12 are substituted or unsubstituted phenyl groups.
- Ar 11 is an unsubstituted phenyl group
- Ar 12 is a phenyl group substituted with a monocyclic group or a condensed ring group
- Ar 11 and Ar 12 are each independently a monocyclic group. Or it may be a phenyl group substituted by a condensed ring group.
- the preferred monocyclic group and condensed ring group as the substituent are as described above. More preferable monocyclic groups as a substituent are a phenyl group and a biphenyl group, and more preferable condensed ring groups as a substituent are a naphthyl group, a phenanthryl group, a fluorenyl group (specifically, 9,9-dimethylfluorine). An oleenyl group), a dibenzofuranyl group, and a benzoanthryl group.
- anthracene derivative represented by the formula (5) include the following.
- the pyrene derivative represented by the formula (6) is as follows.
- Ar 111 and Ar 222 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
- L 1 and L 2 each independently represent a substituted or unsubstituted divalent arylene group or heterocyclic group having 6 to 30 ring carbon atoms.
- m is an integer from 0 to 1
- n is an integer from 1 to 4
- s is an integer from 0 to 1
- t is an integer from 0 to 3.
- L 1 or Ar 111 is bonded to any one of the 1 to 5 positions of pyrene
- L 2 or Ar 222 is bonded to any of the 6 to 10 positions of pyrene.
- L 1 and L 2 in formula (6) are preferably substituted or unsubstituted phenylene group, substituted or unsubstituted biphenylene group, substituted or unsubstituted naphthylene group, substituted or unsubstituted terphenylene group, substituted or unsubstituted A substituted fluorenylene group or a divalent aryl group composed of a combination of these substituents.
- the substituent is the same as the substituent in “substituted or unsubstituted...” In the above formula (1).
- the substituent for L 1 and L 2 is preferably an alkyl group having 1 to 20 carbon atoms.
- M in the formula (6) is preferably an integer of 0 to 1.
- N in the formula (6) is preferably an integer of 1 to 2.
- s is preferably an integer of 0 to 1.
- T in the formula (6) is preferably an integer of 0 to 2.
- the aryl group of Ar 111 and Ar 222 is the same as the aryl group in the above formula (1). Preferably, it is a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, more preferably a substituted or unsubstituted aryl group having 6 to 16 ring carbon atoms.
- aryl group examples include: A phenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a biphenyl group, an anthryl group, and a pyrenyl group.
- the content of the compound represented by the formula (1) is preferably 0.1 to 20% by mass in the organic thin film layer, and preferably 1 to 10% by mass. % Is more preferable.
- the compound represented by the formula (1) and the anthracene derivative or pyrene derivative can be used for a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer in addition to the light emitting layer.
- the organic EL element having a plurality of organic thin film layers includes (anode / hole injection layer / light emitting layer / cathode), (anode / light emitting layer / electron injection layer / cathode), (anode / Hole injection layer / light emitting layer / electron injection layer / cathode), (anode / hole injection layer / hole transport layer / light emitting layer / electron injection layer / cathode) and the like.
- the organic EL element can prevent luminance and lifetime from being reduced due to quenching by forming the organic thin film layer into a multi-layer structure.
- a light emitting material, a doping material, a hole injection material, and an electron injection material can be used in combination.
- the hole injection layer, the light emitting layer, and the electron injection layer may each be formed of two or more layers. In that case, in the case of a hole injection layer, the layer that injects holes from the electrode is a hole injection layer, and the layer that receives holes from the hole injection layer and transports holes to the light emitting layer is a hole transport layer. Call.
- an electron injection layer a layer that injects electrons from an electrode is referred to as an electron injection layer, and a layer that receives electrons from the electron injection layer and transports electrons to a light emitting layer is referred to as an electron transport layer.
- an electron injection layer a layer that injects electrons from an electrode
- an electron transport layer a layer that receives electrons from the electron injection layer and transports electrons to a light emitting layer.
- Each of these layers is selected and used depending on factors such as the energy level of the material, heat resistance, and adhesion to the organic layer or metal electrode.
- Examples of materials other than the above formulas (5) and (6) that can be used for the light emitting layer together with the compound represented by the formula (1) include naphthalene, phenanthrene, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, Condensed polycyclic aromatic compounds such as coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, fluorene, spirofluorene and their derivatives, organometallic complexes such as tris (8-quinolinolato) aluminum, triarylamine derivatives, styrylamine derivatives , Stilbene derivatives, coumarin derivatives, pyran derivatives, oxazone derivatives, benzothiazole derivatives, benzoxazole derivatives, benzimidazole derivatives, pyrazine derivatives, cinnamic acid ester derivatives
- the hole injection layer is a layer containing a substance having a high hole injection property.
- Substances with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, Tungsten oxide, manganese oxide, aromatic amine compound, or high molecular compound (oligomer, dendrimer, polymer, etc.) can also be used.
- the hole transport layer is a layer containing a substance having a high hole transport property.
- An aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used for the hole transport layer.
- a high molecular compound such as poly (N-vinylcarbazole) (abbreviation: PVK) or poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
- PVK N-vinylcarbazole
- PVTPA poly (4-vinyltriphenylamine)
- the layer containing a substance having a high hole-transport property is not limited to a single layer, and two or more layers containing the above substances may be stacked.
- the electron transport layer is a layer containing a substance having a high electron transport property.
- metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes
- heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives
- 3) polymer compounds can be used.
- the electron injection layer is a layer containing a substance having a high electron injection property.
- the electron injection layer includes an alkali metal such as lithium (Li), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), lithium oxide (LiOx), or an alkaline earth metal. Or a compound thereof.
- the organic EL device in the light emitting layer, in addition to at least one selected from the compound represented by the formula (1), a light emitting material, a doping material, a hole injection material, and a hole transport At least one of the material and the electron injection material may be contained in the same layer.
- a protective layer is provided on the surface of the device, or the entire device is protected by silicon oil, resin, etc. Is also possible.
- a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function specifically, 4.0 eV or more.
- ITO indium oxide-tin oxide
- ITO indium oxide-tin oxide
- gold (Au) platinum (Pt), a nitride of a metal material (for example, titanium nitride), or the like can be given.
- a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (specifically, 3.8 eV or less) for the cathode.
- cathode materials include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth such as magnesium (Mg). And other rare earth metals such as alloys, alloys containing them (for example, MgAg, AlLi), and alloys containing these.
- the anode and the cathode may be formed of two or more layers.
- the substrate is also preferably transparent.
- the transparent electrode is set using the above-described conductive material so that predetermined translucency is ensured by a method such as vapor deposition or sputtering.
- the electrode on the light emitting surface preferably has a light transmittance of 10% or more.
- glass, quartz, plastic, or the like can be used as the substrate.
- a flexible substrate may be used.
- the flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate made of polycarbonate or polyvinyl chloride.
- each layer of the organic EL element any of dry film forming methods such as vacuum deposition, sputtering, plasma, and ion plating, and wet film forming methods such as spin coating, dipping, and flow coating can be applied.
- the film thickness is not particularly limited, but must be set to an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied.
- the normal film thickness is suitably in the range of 5 nm to 10 ⁇ m, but more preferably in the range of 10 nm to 0.2 ⁇ m.
- the material for forming each layer is dissolved or dispersed in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane or the like to form a thin film, and any solvent may be used.
- an organic EL material-containing solution containing a compound represented by the formula (1) and a solvent can be used as the organic EL material.
- the organic EL material includes a host material and a dopant material, the dopant material is a compound represented by formula (1), and the host material is at least one selected from compounds represented by formula (5) Is preferable.
- an appropriate resin or additive may be used for improving the film formability and preventing pinholes in the film.
- the organic EL element in one embodiment of the present invention can be used for a flat light emitter such as a flat panel display of a wall-mounted television, a light source such as a copying machine, a printer, a backlight of a liquid crystal display or instruments, a display board, a marker lamp, and the like.
- the compound according to one embodiment of the present invention can be used not only in an organic EL element but also in fields such as an electrophotographic photosensitive member, a photoelectric conversion element, a solar cell, and an image sensor.
- Example 1 Synthesis of Compound 1> Compound 1 was synthesized according to the following scheme.
- the obtained reaction solution was cooled to room temperature, water was added, extraction was performed with toluene, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
- the obtained residue was purified by silica gel column chromatography to obtain 2-methyl-N- (o-tolyl) -5-phenylaniline (10.17 g). The yield in two steps was 69%.
- the obtained reaction solution was cooled to room temperature, water was added, extraction was performed with toluene, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
- the obtained residue was purified by silica gel column chromatography and recrystallization to obtain compound 1 (0.29 g). The yield was 3%.
- the obtained reaction mixture is returned to room temperature, 10% aqueous sodium hydrogen sulfite solution (50 mL) is added, extraction is performed with diethyl ether, and the organic layer is washed with 10% aqueous sodium hydrogen sulfite solution and dried over anhydrous magnesium sulfate.
- the solvent was distilled off under reduced pressure.
- the obtained residue was purified by silica gel column chromatography to obtain 2-bromo-4-iodotoluene (14.5 g). The yield was 49%.
- the obtained reaction mixture was cooled to room temperature and filtered through Celite, and then the solvent was distilled off under reduced pressure.
- the obtained residue was purified by silica gel column chromatography to obtain N, N-bis (2-methyl-5-phenylphenyl) amine (6.03 g). The yield was 61%.
- Tris (dibenzylideneacetone) dipalladium (0) (0.16 g) and tri-t-butylphosphine tetrafluoroborate (0.16 g) were added to the reaction mixture, and the mixture was further refluxed for 5 hours.
- the resulting reaction solution was cooled to room temperature, water was added, and the solid produced in the system was collected by filtration and washed with water and methanol.
- the obtained residue was purified by silica gel column chromatography and recrystallization to obtain compound 2 (2.18 g). The yield was 17%.
- reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 2-methyl-5-phenyl-N- (3-biphenyl) aniline (23 g). The yield was 53%.
- Tris (dibenzylideneacetone) dipalladium (0) (0.23 g) and 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl (BINAP) (0.32 g) were added and stirred for 14 hours.
- the obtained reaction liquid was cooled to room temperature, and the solvent was distilled off under reduced pressure.
- the obtained residue was purified by silica gel column chromatography to obtain 3- (2-methyl-5-phenylanilino) benzonitrile (2.32 g). The yield was 48%.
- Example 8 Synthesis of Compound 8> Compound 8 was synthesized according to the following scheme.
- the obtained reaction liquid was cooled to room temperature, and the solvent was distilled off under reduced pressure.
- the obtained residue was purified by silica gel column chromatography to obtain 4-methyl-3- (2-methyl-5-phenylanilino) benzonitrile (5.25 g). The yield was 63%.
- the obtained reaction solution was cooled to room temperature and extracted with ethyl acetate, and then the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
- the obtained residue was purified by silica gel column chromatography to obtain 4-fluoro-2-phenylbenzonitrile (22.1 g). The yield was 90%.
- the obtained reaction solution was diluted with toluene (150 mL), added to a hydrochloric acid-ice mixture (100 mL), and stirred for 1 hour.
- the obtained mixture was separated, the toluene layer was washed with hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure.
- the obtained residue was purified by silica gel column chromatography to obtain 4- (2-methyl-5-phenylanilino) -2-phenylbenzonitrile (2.73 g). The yield was 30%.
- the obtained reaction liquid was cooled to room temperature, water was added and stirred, and the generated solid was collected by filtration.
- the obtained solid was purified by silica gel column chromatography and recrystallization to obtain compound 9 (4.8 g). The yield was 60%.
- Example 10 ⁇ Production of organic EL element> A 25 mm ⁇ 75 mm ⁇ 1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes. A glass substrate with a transparent electrode line after washing is mounted on a substrate holder of a vacuum vapor deposition apparatus, and first, compound HI-1 is vapor-deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed. A compound HI-1 film having a thickness of 10 nm was formed. This HI-1 film functions as a hole injection layer.
- ITO transparent electrode anode
- UV ozone cleaning UV ozone cleaning
- the compound HT-1 was vapor-deposited, and an HT-1 film having a thickness of 80 nm was formed on the HI-1 film.
- This HT-1 film functions as a first hole transport layer.
- a compound HT-2 was vapor-deposited to form a 10 nm thick HT-2 film on the HT-1 film.
- This HT-2 film functions as a second hole transport layer.
- BH-1 (host material) and compound 1 (dopant material) were co-evaporated on the HT-2 film so that the ratio (weight ratio) of the compound was 4% to form a light-emitting layer having a thickness of 25 nm.
- ET-1 was vapor-deposited on this light emitting layer to form an electron transport layer having a thickness of 25 nm.
- ET-2 which is an electron injection material, was vapor-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 nm.
- LiF was vapor-deposited on this electron injection layer to form a 1-nm thick LiF film.
- Metal Al was vapor-deposited on this LiF film to form a metal cathode having a thickness of 80 nm.
- the organic EL element was produced as described above. The compounds used are shown below.
- the manufactured organic EL device was evaluated as follows. That is, a voltage was applied to the organic EL element so that the current density was 10 mA / cm 2, and the EL emission spectrum was measured with a spectral radiance meter (CS-1000: manufactured by Konica Minolta). External quantum efficiency EQE (%) and emission peak wavelength were calculated from the obtained spectral radiance spectrum. The results are shown in Table 1.
- Examples 11 to 17 and Comparative Examples 1 to 6 An organic EL device was prepared and evaluated in the same manner as in Example 10 except that the compounds shown in Table 1 were used instead of Compound 1. The results are shown in Table 1.
- Example 18 ⁇ Production of organic EL element> A 25 mm ⁇ 75 mm ⁇ 1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes. A glass substrate with a transparent electrode line after washing is mounted on a substrate holder of a vacuum vapor deposition apparatus, and first, compound HI-1 is vapor-deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed. A compound HI-1 film having a thickness of 5 nm was formed. This HI-1 film functions as a hole injection layer.
- the compound HT-1 was vapor-deposited to form a 90 nm-thick HT-1 film on the HI-1 film.
- This HT-1 film functions as a first hole transport layer.
- the compound HT-2 was vapor-deposited, and an HT-2 film having a thickness of 5 nm was formed on the HT-1 film.
- This HT-2 film functions as a second hole transport layer.
- BH-2 (host material) and compound 1 (dopant material) were co-evaporated on the HT-2 film so that the ratio (weight ratio) of the compound was 4% to form a light emitting layer having a thickness of 25 nm.
- ET-3 was evaporated on this light emitting layer to form an electron transport layer having a thickness of 5 nm.
- ET-2 and ET-4 were vapor deposited at a weight ratio of 1: 1 to form an electron injection layer having a thickness of 25 nm.
- ET-4 was vapor-deposited on this electron injection layer to form an ET-4 film having a thickness of 1 nm.
- Metal Al was deposited on the ET-4 film to form a metal cathode having a thickness of 80 nm.
- the organic EL element was produced as described above. The compounds used are shown below.
- the manufactured organic EL device was evaluated as follows. That is, a voltage was applied to the organic EL element so that the current density was 10 mA / cm 2, and the EL emission spectrum was measured with a spectral radiance meter (CS-1000: manufactured by Konica Minolta). External quantum efficiency EQE (%) and emission peak wavelength were calculated from the obtained spectral radiance spectrum. The results are shown in Table 2.
- the compound according to one embodiment of the present invention has high efficiency by simultaneously having an ortho-position alkyl group and one or more aryl groups in at least one of the side chain substituents (phenyl group) of the diaminopyrene structure. Is obtained.
- the presence of an alkyl group in the ortho position of the phenyl group is considered to reduce energy loss when converting the energy obtained from the host material into light.
- the light emitting layer host material This is considered to contribute to the improvement of the light emission efficiency because of the proper interaction of the light and smooth energy transfer and light emission.
- Comparative Compounds 1, 4, and 6 reveals that the alkyl group at the ortho position contributes to the improvement of luminous efficiency, and the comparison with Comparative Compounds 3 and 5 contributes to the emission effect. You can see that Further, when compared with a compound in which a condensed ring substituent is directly connected in addition to the central pyrene as in Comparative Compound 2, the compound according to one embodiment of the present invention has reduced deactivation due to vibration of a side chain substituent. It is conceivable and higher efficiency is obtained.
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Abstract
Description
下記式(1)で表される化合物。
Raは、それぞれ、置換もしくは無置換の炭素数1~15のアルキル基又は置換もしくは無置換の炭素数3~15の環状アルキル基であり、
Rb1~Rb4は、それぞれ、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~15のアルキル基、置換もしくは無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、置換もしくは無置換の炭素数1~15のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数1~15のアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数6~30のアリールアミノ基、置換もしくは無置換の環形成炭素数6~30のアリール基、又は置換もしくは無置換の環形成原子数3~30のヘテロアリール基であり、
Rc1~Rc10は、それぞれ、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~15のアルキル基、置換もしくは無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、置換もしくは無置換の炭素数1~15のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数1~15のアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数6~30のアリールアミノ基、置換もしくは無置換の環形成炭素数6~30のアリール基、置換もしくは無置換の環形成原子数3~30のヘテロアリール基、又は窒素原子と結合する単結合であり、
*は、Rc1~Rc10のいずれかと窒素原子との結合位置を示し、
xは、0~3の整数であり、
yは、0~4の整数であり、
zは、それぞれ0~5の整数であり、
xが2以上の整数である場合、複数のRb1はそれぞれ同一でも異なっていてもよく、yが2以上の整数である場合、複数のRb2はそれぞれ同一でも異なっていてもよく、zが2以上の整数である場合、複数のRb3又はRb4はそれぞれ同一でも異なっていてもよい。)
Raは、それぞれ、置換もしくは無置換の炭素数1~15のアルキル基又は置換もしくは無置換の炭素数3~15の環状アルキル基である。
Rb1~Rb4は、それぞれ、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~15のアルキル基、置換もしくは無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、置換もしくは無置換の炭素数1~15のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数1~15のアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数6~30のアリールアミノ基、置換もしくは無置換の環形成炭素数6~30のアリール基、又は置換もしくは無置換の環形成原子数3~30のヘテロアリール基である。
Rc1~Rc10は、それぞれ、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~15のアルキル基、置換もしくは無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、置換もしくは無置換の炭素数1~15のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数1~15のアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数6~30のアリールアミノ基、置換もしくは無置換の環形成炭素数6~30のアリール基、置換もしくは無置換の環形成原子数3~30のヘテロアリール基、又は窒素原子と結合する単結合である。
*は、Rc1~Rc10のいずれかと窒素原子との結合位置を示す。
xは、0~3の整数であり、yは、0~4の整数であり、zは、それぞれ0~5の整数である。xが2以上の整数である場合、複数のRb1はそれぞれ同一でも異なっていてもよく、yが2以上の整数である場合、複数のRb2はそれぞれ同一でも異なっていてもよく、zが2以上の整数である場合、複数のRb3又はRb4はそれぞれ同一でも異なっていてもよい。
この場合、上記化合物はアリールアミノ基の2置換体となる。
Rc2~Rc5、Rc7~Rc10は、それぞれ、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~15のアルキル基、置換もしくは無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、置換もしくは無置換の炭素数1~15のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数1~15のアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数6~30のアリールアミノ基、置換もしくは無置換の環形成炭素数6~30のアリール基、又は置換もしくは無置換の環形成原子数3~30のヘテロアリール基である。
Rc3及びRc8は、好ましくは、それぞれ水素原子、炭素数1~6のアルキル基又は炭素数1~6の環状アルキル基である。
Rc2、Rc4~Rc10は、それぞれ、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~15のアルキル基、置換もしくは無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、置換もしくは無置換の炭素数1~15のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数1~15のアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数6~30のアリールアミノ基、置換もしくは無置換の環形成炭素数6~30のアリール基、又は置換もしくは無置換の環形成原子数3~30のヘテロアリール基である。
Rc7は、好ましくは、置換もしくは無置換の炭素数1~15のアルキル基又は置換もしくは無置換の炭素数3~15の環状アルキル基である。
なお、上記記載はRb1とArがパラ位に置換することを妨げるものではなく、これらがパラ位に置換していてもよい。
Rb3’及びRb4’は、それぞれ、置換もしくは無置換の炭素数1~15のアルキル基又は置換もしくは無置換の炭素数3~15の環状アルキル基であり、
z1は、それぞれ、0~4の整数である。
アルキル基の炭素数は、1~10が好ましく、1~6がさらに好ましい。中でもメチル基、エチル基、プロピル基、イソプロピル基、n-ブチル基、s-ブチル基、イソブチル基、t-ブチル基、n-ペンチル基、n-ヘキシル基が好ましい。
アリール基は、環形成炭素数が6~20であることが好ましく、より好ましくは6~12であり、上述したアリール基の中でもフェニル基、ビフェニル基、が特に好ましい。
アリールチオ基は、-SZと表され、Zの例として上記のアリール基の例が挙げられる。
ヘテロアリール基は、好ましくは、ジベンゾフラニル基、ジベンゾチオフェニル基、又はカルバゾリル基であり、より好ましくは、1-ジベンゾフラニル基、2-ジベンゾフラニル基、3-ジベンゾフラニル基、4-ジベンゾフラニル基、1-ジベンゾチオフェニル基、2-ジベンゾチオフェニル基、3-ジベンゾチオフェニル基、4-ジベンゾチオフェニル基である。
好ましくは、発光層が上記化合物を含有する。発光層は上記化合物のみから構成することも、ホストとして、又はドーパントとして含むこともできる。
R101~R108は、それぞれ独立して、水素原子、置換若しくは無置換の環形成原子数5~50(好ましくは5~30、より好ましくは5~20、さらに好ましくは5~12)の単環基、置換若しくは無置換の環形成原子数8~50(好ましくは8~30、より好ましくは8~20、さらに好ましくは8~14)の縮合環基、前記単環基と前記縮合環基との組合せから構成される基、置換若しくは無置換の炭素数1~50(好ましくは1~20、より好ましくは1~10、さらに好ましくは1~6)のアルキル基、置換若しくは無置換の環形成炭素数3~50(好ましくは3~20、より好ましくは3~10、さらに好ましくは5~8)のシクロアルキル基、置換若しくは無置換の炭素数1~50(好ましくは1~20、より好ましくは1~10、さらに好ましくは1~6)のアルコキシ基、置換若しくは無置換の炭素数7~50(好ましくは7~20、より好ましくは7~14)のアラルキル基、置換若しくは無置換の環形成炭素数6~50(好ましくは6~20、より好ましくは6~12)のアリールオキシ基、置換若しくは無置換のシリル基、ハロゲン原子、及びシアノ基からなる群から選ばれる基である。
環形成原子数5~50の単環基の具体例としては、フェニル基、ビフェニリル基、ターフェニリル基、クォーターフェニリル基等の芳香族基と、ピリジル基、ピラジル基、ピリミジル基、トリアジニル基、フリル基、チエニル基等の複素環基が好ましい。
上記単環基としては、中でも、フェニル基、ビフェニリル基、ターフェニリル基が好ましい。
環形成原子数8~50の縮合環基の具体例としては、ナフチル基、フェナントリル基、アントリル基、クリセニル基、ベンゾアントリル基、ベンゾフェナントリル基、トリフェニレニル基、ベンゾクリセニル基、インデニル基、フルオレニル基、ベンゾフルオレニル基、ジベンゾフルオレニル基、フルオランテニル基、ベンゾフルオランテニル基等の縮合芳香族環基や、ベンゾフラニル基、ベンゾチオフェニル基、インドリル基、ジベンゾフラニル基、ジベンゾチオフェニル基、カルバゾリル基、キノリル基、フェナントロリニル基等の縮合複素環基が好ましい。
上記フルオレニル基は、9位に置換基を1つ又は2つ有していてもよく、置換基としては、例えば、アルキル基、アリール基、アルキルシリル基、アリールシリル基、アルコキシ基等が挙げられる。このようなフルオレニル基の具体例としては、例えば、9,9-ジメチルフルオレニル基や9,9-ジフェニルフルオレニル基等が挙げられる。以後、フルオレニル基と記載した場合には、特筆しない限り同様の置換基を有していてもよいものとする。
尚、Ar11及びAr12の置換基は、上述の単環基又は縮合環基が好ましい。
アントラセン誘導体(A)は、式(5)におけるAr11及びAr12が、それぞれ独立して、置換若しくは無置換の環形成原子数8~50の縮合環基である。当該アントラセン誘導体としては、Ar11及びAr12は同一でも異なっていてもよい。
アントラセン誘導体(B)は、式(5)におけるAr11及びAr12の一方が置換若しくは無置換の環形成原子数5~50の単環基であり、Ar11及びAr12の他方が置換若しくは無置換の環形成原子数8~50の縮合環基である。
アントラセン誘導体(B)の好ましい形態としては、Ar12がナフチル基、フェナントリル基、ベンゾアントリル基、フルオレニル基(具体的には、9,9-ジメチルフルオレニル基等)、又はジベンゾフラニル基であり、Ar11が無置換フェニル基、又は、単環基又は縮合環基(例えば、フェニル基、ビフェニル基、ナフチル基、フェナントリル基、フルオレニル基(具体的には、9,9-ジメチルフルオレニル基等)、ジベンゾフラニル基)で置換されたフェニル基である誘導体が挙げられる。好ましい単環基、縮合環基の具体的な基は上述した通りである。
アントラセン誘導体(B)の別の好ましい形態としては、Ar12が置換若しくは無置換の環形成原子数8~50の縮合環基であり、Ar11が無置換のフェニル基である誘導体が挙げられる。この場合、縮合環基としては、フェナントリル基、フルオレニル基(具体的には、9,9-ジメチルフルオレニル基等)、ジベンゾフラニル基、ベンゾアントリル基が特に好ましい。
アントラセン誘導体(C)は、式(5)におけるAr11及びAr12が、それぞれ独立して、置換若しくは無置換の環形成原子数5~50の単環基である。
アントラセン誘導体(C)の好ましい形態としては、Ar11、Ar12ともに置換若しくは無置換のフェニル基である誘導体が挙げられる。さらに好ましい形態として、Ar11が無置換のフェニル基であり、Ar12が単環基又は縮合環基で置換されたフェニル基である場合と、Ar11、Ar12がそれぞれ独立して単環基又は縮合環基で置換されたフェニル基である場合がある。
前記置換基としての好ましい単環基、縮合環基の具体例は上述した通りである。置換基としてのさらに好ましい単環基は、フェニル基、ビフェニル基であり、置換基としてのさらに好ましい縮合環基は、ナフチル基、フェナントリル基、フルオレニル基(具体的には、9,9-ジメチルフルオレニル基等)、ジベンゾフラニル基、ベンゾアントリル基である。
L1及びL2は、それぞれ独立して、置換若しくは無置換の環形成炭素数6~30の2価のアリーレン基又は複素環基を示す。
mは0~1の整数、nは1~4の整数、sは0~1の整数、tは0~3の整数である。
また、L1又はAr111はピレンの1~5位のいずれかに結合し、L2又はAr222はピレンの6~10位のいずれかに結合する。
また、この置換基としては、上記式(1)における「置換若しくは無置換の・・・」における置換基と同様である。L1及びL2の置換基は、好ましくは、炭素数1~20のアルキル基である。
Ar111及びAr222のアリール基は、上記式(1)におけるアリール基と同様である。好ましくは、置換若しくは無置換の環形成炭素数6~20のアリール基、より好ましくは、置換若しくは無置換の環形成炭素数6~16のアリール基であり、アリール基の好ましい具体例としては、フェニル基、ナフチル基、フェナントリル基、フルオレニル基、ビフェニル基、アントリル基、ピレニル基である。
陽極及び陰極は、必要があれば二層以上の層構成により形成されていてもよい。
基板としては、例えば、ガラス、石英、プラスチックなどを用いることができる。また、可撓性基板を用いてもよい。可撓性基板とは、折り曲げることができる(フレキシブル)基板のことであり、例えば、ポリカーボネート、ポリ塩化ビニルからなるプラスチック基板等が挙げられる。
このような湿式成膜法に適した溶液として、有機EL材料として式(1)で表される化合物と溶媒とを含有する有機EL材料含有溶液を用いることができる。
アルゴン雰囲気下、5-ブロモ-2-メチルアニリン(10.0g)、フェニルボロン酸(8.52g)、テトラキス(トリフェニルホスフィン)パラジウム(0)(1.86g)、2M炭酸ナトリウム水溶液(80.6mL)及び1,2-ジメトキシエタン(DME)(135mL)の混合物を5時間還流した。得られた反応液を室温に冷却し、ジクロロメタンで抽出を行った後、有機層を水で洗浄し、無水硫酸マグネシウムで乾燥し、溶媒を減圧留去した。得られた2-メチル-5-フェニルアニリンの粗精製物をそのまま次工程に用いた。
アルゴン雰囲気下、工程(1-1)で得た2-メチル-5-フェニルアニリンの粗精製物、2-ブロモトルエン(7.35g)、トリス(ジベンジリデンアセトン)ジパラジウム(0)(0.98g)、2,2’-ビス(ジフェニルホスフィノ)-1,1’-ビナフチル(BINAP)(1.67g)、ナトリウム-t-ブトキシド(7.75g)及びトルエン(270g)の混合物を5時間還流した。得られた反応液を室温に冷却し、水を加え、トルエンで抽出を行った後、有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、溶媒を減圧留去した。得られた残渣をシリカゲルカラムクロマトグラフィーで精製し、2-メチル-N-(o-トリル)-5-フェニルアニリン(10.17g)を得た。2工程で収率69%であった。
アルゴン雰囲気下、1,6-ジブロモピレン(5.82g)、工程(1-2)で得た2-メチル-N-(o-トリル)-5-フェニルアニリン(10.17g)、トリス(ジベンジリデンアセトン)ジパラジウム(0)(0.89g)、テトラフルオロほう酸トリ-t-ブチルホスフィン(0.56g)、ナトリウム-t-ブトキシド(6.22g)及びトルエン(162mL)の混合物を7時間還流した。得られた反応液を室温に冷却し、水を加え、トルエンで抽出を行った後、有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、溶媒を減圧留去した。得られた残渣をシリカゲルカラムクロマトグラフィー及び再結晶で精製し、化合物1(0.29g)を得た。収率3%であった。得られたものは、マススペクトル分析の結果化合物1であり、分子量744.35に対しm/e=744であった。
アルゴン雰囲気下、3-ブロモ-4-メチルアニリン(18.6g)と6M塩酸(80mL)の混合物を-5℃に冷却し、0℃以下を保ちながら亜硝酸ナトリウム(7.35g)の水溶液(15mL)を滴下した後、-8℃にて45分間撹拌した。得られた混合物に、0℃以下を保ちながらヨウ化カリウム(33.2g)を3時間かけて加えた。得られた反応混合物を室温に戻し、10%亜硫酸水素ナトリウム水溶液(50mL)を加え、ジエチルエーテルで抽出を行った後、有機層を10%亜硫酸水素ナトリウム水溶液で洗浄し、無水硫酸マグネシウムで乾燥し、溶媒を減圧留去した。得られた残渣をシリカゲルカラムクロマトグラフィーで精製し、2-ブロモ-4-ヨードトルエン(14.5g)を得た。収率49%であった。
アルゴン雰囲気下、工程(2-1)で得た2-ブロモ-4-ヨードトルエン(14.5g)、フェニルボロン酸(6.35g)、テトラキス(トリフェニルホスフィン)パラジウム(0)(1.69g)、炭酸カリウム(20.2g)、1,4-ジオキサン(117mL)及び水(13mL)の混合物を3時間還流した。得られた反応混合物を室温に冷却し、ジクロロメタンで抽出を行った後、得られた有機層を飽和食塩水で洗浄し、溶媒を減圧留去した。得られた残渣をシリカゲルカラムクロマトグラフィーで精製し、2-ブロモ-1-メチル-4-フェニルベンゼン(8.6g)を得た。収率71%であった。
アルゴン雰囲気下、実施例1の工程(1-1)と同様の操作で、5-ブロモ-2-メチルアニリン6.59gから製造した2-メチル-5-フェニルアニリンの粗精製物、工程(2-2)で得た2-ブロモ-1-メチル-4-フェニルベンゼン(7.0g)、トリス(ジベンジリデンアセトン)ジパラジウム(0)(0.65g)、BINAP(1.1g)、ナトリウム-t-ブトキシド(5.1g)及びトルエン(100mL)の混合物を4.5時間還流した。得られた反応混合物を室温に冷却し、セライト濾過を行った後、溶媒を減圧留去した。得られた残渣をシリカゲルカラムクロマトグラフィーで精製し、N,N-ビス(2-メチル-5-フェニルフェニル)アミン(6.03g)を得た。収率61%であった。
アルゴン雰囲気下、1,6-ジブロモピレン(5.09g)、工程(2-3)で得たN,N-ビス(2-メチル-5-フェニルフェニル)アミン(11.87g)、トリス(ジベンジリデンアセトン)ジパラジウム(0)(0.78g)、テトラフルオロほう酸トリ-t-ブチルホスフィン(0.82g)、ナトリウム-t-ブトキシド(4.08g)及びトルエン(150mL)の混合物を6.5時間還流した。反応混合物に、トリス(ジベンジリデンアセトン)ジパラジウム(0)(0.16g)及びテトラフルオロほう酸トリ-t-ブチルホスフィン(0.16g)を加え、さらに5時間還流した。得られた反応液を室温に冷却し、水を加え、系内に生成した固体をろ取して水、メタノールで洗浄した。得られた残渣をシリカゲルカラムクロマトグラフィー及び再結晶で精製し、化合物2(2.18g)を得た。収率17%であった。得られたものは、マススペクトル分析の結果化合物2であり、分子量896.41に対しm/e=896であった。
2-メチル-N-(o-トリル)-5-フェニルアニリン(62.6g)、アセトニトリル(130mL)及び氷水(200g)に、0℃以下に保ちながら濃塩酸(169mL)を滴下し30分間撹拌した。得られた反応液に、-5℃にて亜硝酸ナトリウム(28.4g)の水溶液(250mL)を滴下し、-5℃にて1時間撹拌した。得られた反応液に、-2℃に保ちながらヨウ化カリウム(142g)の水溶液(200mL)を加え、反応液を室温に戻し終夜撹拌した。得られた反応液にクロロホルム、チオ硫酸ナトリウム水溶液を加え、撹拌した。反応液を分液し、クロロホルム層を水で洗浄し、溶媒を減圧留去した。得られた残渣をシリカゲルカラムクロマトグラフィーで精製し、3-ヨード-4-メチルビフェニル(73.4g)を得た。収率73%であった。
アルゴン雰囲気下、工程(6-1)で合成した3-ヨード-4-メチルビフェニル(38g)、3-アミノビフェニル(43.7g)、トリス(ジベンジリデンアセトン)ジパラジウム(0)(4.57g)、2,2’-ビス(ジフェニルホスフィノ)-1,1’-ビナフチル(BINAP)(2.41g)、ナトリウム-t-ブトキシド(27.3g)及びキシレン(820mL)の混合物を105℃で9時間撹拌した。得られた反応液を室温に冷却し、溶媒を減圧留去し、シリカゲルカラムクロマトグラフィーで精製し、2-メチル-5-フェニル-N-(3-ビフェニル)アニリン(23g)を得た。収率53%であった。
アルゴン雰囲気下、1,6-ジブロモピレン(10g)、工程(6-2)で得られた2-メチル-5-フェニル-N-(3-ビフェニル)アニリン(20.5g)、酢酸パラジウム(II)(0.25g)、トリ-t-ブチルホスフィン(0.45g)、LiHMDSのトルエン溶液(1M、67mL)及びキシレン(300mL)の混合物を120℃にて18時間撹拌した。得られた反応液を室温に冷却し、濃縮後、シリカゲルカラムクロマトグラフィー及び再結晶で精製し、化合物6(17.9g)を得た。収率74%であった。得られたものは、マススペクトル分析の結果化合物6であり、分子量868.38に対しm/e=868であった。
アルゴン雰囲気下、3-アミノベンゾニトリル(2.41g)、3-ヨード-4-メチルビフェニル(5.0g)、トリス(ジベンジリデンアセトン)ジパラジウム(0)(0.23g)、2,2’-ビス(ジフェニルホスフィノ)-1,1’-ビナフチル(BINAP)(0.32g)、ナトリウム-t-ブトキシド(2.45g)及びキシレン(57mL)の混合物を110℃で1時間、次いで130℃で2時間撹拌した。トリス(ジベンジリデンアセトン)ジパラジウム(0)(0.23g)、2,2’-ビス(ジフェニルホスフィノ)-1,1’-ビナフチル(BINAP)(0.32g)を加え14時間撹拌した。得られた反応液を室温に冷却し、溶媒を減圧留去した。得られた残渣をシリカゲルカラムクロマトグラフィーで精製し、3-(2-メチル-5-フェニルアニリノ)ベンゾニトリル(2.32g)を得た。収率48%であった。
アルゴン雰囲気下、1,6-ジブロモ-3,8-ジイソプロピルピレン(1.65g)、工程(7-1)で得た3-(2-メチル-5-フェニルアニリノ)ベンゾニトリル(2.32g)、酢酸パラジウム(II)(0.033g)、テトラフルオロほう酸トリ-t-ブチルホスフィン(0.086g)、LiHMDSのトルエン溶液(1M、8.9mL)及びキシレン(74mL)の混合物を120℃にて終夜撹拌した。得られた反応液を室温に冷却し、濃縮した後、シリカゲルカラムクロマトグラフィー及び再結晶で精製し、化合物7(1.9g)を得た。収率60%であった。得られたものは、マススペクトル分析の結果化合物7であり、分子量850.40に対しm/e=850であった。
アルゴン雰囲気下、3-ブロモ-4-メチルベンゾニトリル(5.88g)、2-メチル-N-(o-トリル)-5-フェニルアニリン(5.0g)、トリス(ジベンジリデンアセトン)ジパラジウム(0)(0.50g)、2,2’-ビス(ジフェニルホスフィノ)-1,1’-ビナフチル(BINAP)(0.68g)、ナトリウム-t-ブトキシド(3.93g)及びキシレン(91mL)の混合物を110℃で3.5時間撹拌した。得られた反応液を室温に冷却し、溶媒を減圧留去した。得られた残渣をシリカゲルカラムクロマトグラフィーで精製し、4-メチル-3-(2-メチル-5-フェニルアニリノ)ベンゾニトリル(5.25g)を得た。収率63%であった。
アルゴン雰囲気下、1,6-ジブロモ-3,8-ジイソプロピルピレン(5.0g)、工程(8-1)と同様の操作で得た4-メチル-3-(2-メチル-5-フェニルアニリノ)ベンゾニトリル(7.39g)、酢酸パラジウム(II)(0.10g)、テトラフルオロほう酸トリ-t-ブチルホスフィン(0.26g)、LiHMDSのトルエン溶液(1M、27mL)及びキシレン(225mL)の混合物を125℃にて6時間撹拌した。得られた反応液を室温に冷却し、シリカゲルカラムクロマトグラフィー及び再結晶で精製し、化合物8(4.26g)を得た。収率43%であった。得られたものは、マススペクトル分析の結果化合物8であり、分子量878.43に対しm/e=878であった。
アルゴン雰囲気下、2-ブロモ-4-フルオロベンゾニトリル(25.0g)、フェニルボロン酸(18.32g)、テトラキス(トリフェニルホスフィン)パラジウム(0)(2.89g)、2M炭酸ナトリウム水溶液(125mL)及び1,2-ジメトキシエタン(DME)(250mL)の混合物を80℃で3時間撹拌した。得られた反応液を室温に冷却し、酢酸エチルで抽出を行った後、有機層を水、飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、溶媒を減圧留去した。得られた残渣をシリカゲルカラムクロマトグラフィーで精製し、4-フルオロ-2-フェニルベンゾニトリル(22.1g)を得た。収率90%であった。
2-メチル-N-(o-トリル)-5-フェニルアニリン(9.16g)のDMSO(32mL)溶液に水素化ナトリウム(2.2g)を加え、室温で1時間撹拌した。得られた反応液に(9-1)で合成した4-フルオロ-2-フェニルベンゾニトリル(4.93g)のDMSO(31mL)溶液を、水冷下で1時間かけて滴下し、6時間撹拌した。得られた反応液をトルエン(150mL)で希釈し、塩酸-氷の混合物中(100mL)に加え、1時間撹拌した。得られた混合物を分液し、トルエン層を塩酸、飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、溶媒を減圧留去した。得られた残渣をシリカゲルカラムクロマトグラフィーで精製し、4-(2-メチル-5-フェニルアニリノ)-2-フェニルベンゾニトリル(2.73g)を得た。収率30%であった。
アルゴン雰囲気下、1,6-ジブロモ-3,8-ジイソプロピルピレン(3.5g)、工程(9-2)と同様の操作で得た4-(2-メチル-5-フェニルアニリノ)-2-フェニルベンゾニトリル(5.68g)、酢酸パラジウム(II)(0.07g)、テトラフルオロほう酸トリ-t-ブチルホスフィン(0.18g)、LiHMDSのトルエン溶液(1M、18.9mL)及びキシレン(158mL)の混合物を125℃にて6時間撹拌した。得られた反応液を室温に冷却し、水を加え撹拌し、生成した固体をろ取した。得られた固体をシリカゲルカラムクロマトグラフィー及び再結晶で精製し、化合物9(4.8g)を得た。収率60%であった。得られたものは、マススペクトル分析の結果化合物9であり、分子量1002.47に対しm/e=1002であった。
<有機EL素子の作製>
25mm×75mm×1.1mm厚のITO透明電極(陽極)付きガラス基板(ジオマティック社製)をイソプロピルアルコール中で超音波洗浄を5分間行なった後、UVオゾン洗浄を30分間行なった。
洗浄後の透明電極ライン付きガラス基板を真空蒸着装置の基板ホルダーに装着し、まず透明電極ラインが形成されている側の面上に透明電極を覆うようにして化合物HI-1を蒸着し、膜厚10nmの化合物HI-1膜を形成した。このHI-1膜は、正孔注入層として機能する。
HT-1膜の成膜に続けて化合物HT-2を蒸着し、HT-1膜上に膜厚10nmのHT-2膜を成膜した。このHT-2膜は第2の正孔輸送層として機能する。
HT-2膜上にBH-1(ホスト材料)及び化合物1(ドーパント材料)を化合物の割合(重量比)が4%となるように共蒸着し、膜厚25nmの発光層を成膜した。
以上のようにして有機EL素子を作製した。用いた化合物を以下に示す。
製造した有機EL素子について以下のように評価を行った。即ち、電流密度が10mA/cm2となるように有機EL素子に電圧を印加し、EL発光スペクトルを分光放射輝度計(CS-1000:コニカミノルタ社製)にて計測した。得られた分光放射輝度スペクトルから、外部量子効率EQE(%)及び発光ピーク波長を算出した。結果を表1に示す。
<有機EL素子の作製>
25mm×75mm×1.1mm厚のITO透明電極(陽極)付きガラス基板(ジオマティック社製)をイソプロピルアルコール中で超音波洗浄を5分間行なった後、UVオゾン洗浄を30分間行なった。
洗浄後の透明電極ライン付きガラス基板を真空蒸着装置の基板ホルダーに装着し、まず透明電極ラインが形成されている側の面上に透明電極を覆うようにして化合物HI-1を蒸着し、膜厚5nmの化合物HI-1膜を形成した。このHI-1膜は、正孔注入層として機能する。
このHI-1膜の成膜に続けて化合物HT-1を蒸着し、HI-1膜上に膜厚90nmのHT-1膜を成膜した。このHT-1膜は第1の正孔輸送層として機能する。
HT-1膜の成膜に続けて化合物HT-2を蒸着し、HT-1膜上に膜厚5nmのHT-2膜を成膜した。このHT-2膜は第2の正孔輸送層として機能する。
HT-2膜上にBH-2(ホスト材料)及び化合物1(ドーパント材料)を化合物の割合(重量比)が4%となるように共蒸着し、膜厚25nmの発光層を成膜した。
以上のようにして有機EL素子を作製した。用いた化合物を以下に示す。
製造した有機EL素子について以下のように評価を行った。即ち、電流密度が10mA/cm2となるように有機EL素子に電圧を印加し、EL発光スペクトルを分光放射輝度計(CS-1000:コニカミノルタ社製)にて計測した。得られた分光放射輝度スペクトルから、外部量子効率EQE(%)及び発光ピーク波長を算出した。結果を表2に示す。
本発明の一態様に係る化合物は、ジアミノピレン構造の一方の側鎖置換基(フェニル基)の少なくとも1つに、オルト位のアルキル基と1以上のアリール基を同時に有することにより、高効率化が得られる。フェニル基のオルト位にアルキル基が存在することにより、ホスト材料から得たエネルギーを光に変換する際のエネルギーロスを低減できると考えられ、1以上のアリール基を有することで発光層ホスト材料との相互作用性が適正化し、円滑なエネルギー移動と発光が行われるため、発光効率の向上に寄与すると考えられる。
比較化合物1、4及び6との比較により、当該オルト位のアルキル基が発光効率向上に寄与していることが分かり、比較化合物3及び5との比較により、アリール基の存在が発光効果に寄与していることが分かる。また、比較化合物2のように、中心ピレン以外に縮合環の置換基が直結するものと比較した場合、本発明の一態様に係る化合物は側鎖置換基の振動による失活が低減されると考えられ、より高い効率が得られている。
本願のパリ優先の基礎となる日本出願明細書の内容を全てここに援用する。
Claims (32)
- 下記式(1)で表される化合物。
Raは、それぞれ、置換もしくは無置換の炭素数1~15のアルキル基又は置換もしくは無置換の炭素数3~15の環状アルキル基であり、
Rb1~Rb4は、それぞれ、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~15のアルキル基、置換もしくは無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、置換もしくは無置換の炭素数1~15のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数1~15のアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数6~30のアリールアミノ基、置換もしくは無置換の環形成炭素数6~30のアリール基、又は置換もしくは無置換の環形成原子数3~30のヘテロアリール基であり、
Rc1~Rc10は、それぞれ、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~15のアルキル基、置換もしくは無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、置換もしくは無置換の炭素数1~15のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数1~15のアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数6~30のアリールアミノ基、置換もしくは無置換の環形成炭素数6~30のアリール基、置換もしくは無置換の環形成原子数3~30のヘテロアリール基、又は窒素原子と結合する単結合であり、
*は、Rc1~Rc10のいずれかと窒素原子との結合位置を示し、
xは、0~3の整数であり、
yは、0~4の整数であり、
zは、それぞれ0~5の整数であり、
xが2以上の整数である場合、複数のRb1はそれぞれ同一でも異なっていてもよく、yが2以上の整数である場合、複数のRb2はそれぞれ同一でも異なっていてもよく、zが2以上の整数である場合、複数のRb3又はRb4はそれぞれ同一でも異なっていてもよい。) - Rc1~Rc10が、それぞれ、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~15のアルキル基、置換もしくは無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、置換もしくは無置換の炭素数1~15のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数1~15のアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数6~30のアリール基、置換もしくは無置換の環形成原子数3~30のヘテロアリール基、又は窒素原子と結合する単結合である請求項1又は2に記載の化合物。
- 下記式(4)で表される請求項1~4のいずれかに記載の化合物。
Rc2~Rc5、Rc7~Rc10は、それぞれ、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~15のアルキル基、置換もしくは無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、置換もしくは無置換の炭素数1~15のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数1~15のアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数6~30のアリールアミノ基、置換もしくは無置換の環形成炭素数6~30のアリール基、又は置換もしくは無置換の環形成原子数3~30のヘテロアリール基である。) - Rc3及びRc8が、それぞれ水素原子、炭素数1~6のアルキル基又は炭素数1~6の環状アルキル基である請求項6に記載の化合物。
- 下記式(5)で表される請求項1~4のいずれかに記載の化合物。
Rc2、Rc4~Rc10は、それぞれ、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~15のアルキル基、置換もしくは無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、置換もしくは無置換の炭素数1~15のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数1~15のアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数6~30のアリールアミノ基、置換もしくは無置換の環形成炭素数6~30のアリール基、又は置換もしくは無置換の環形成原子数3~30のヘテロアリール基である。) - Rc7が、置換もしくは無置換の炭素数1~15のアルキル基又は置換もしくは無置換の炭素数3~15の環状アルキル基である請求項9に記載の化合物。
- Rb1が結合するベンゼン環含有基において、Rb1とArのいずれもがN原子との結合位置に対してパラ位に結合せず、かつRb2が結合するベンゼン環含有基において、Rb2がN原子との結合位置に対してパラ位に結合しない請求項1~10のいずれかに記載の化合物。
- Rb1~Rb4が、それぞれ、置換もしくは無置換の炭素数1~15のアルキル基、置換もしくは無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、置換もしくは無置換の炭素数1~15のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数1~15のアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数6~30のアリールアミノ基、置換もしくは無置換の環形成炭素数6~30のアリール基、又は置換もしくは無置換の環形成原子数3~30のヘテロアリール基である請求項1~13のいずれかに記載の化合物。
- Rb1~Rb4が、それぞれ置換もしくは無置換の炭素数1~15のアルキル基、置換または無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、又は置換もしくは無置換の環形成炭素数6~30のアリール基である請求項1~14のいずれかに記載の化合物。
- Raが、それぞれ置換もしくは無置換の炭素数1~6のアルキル基である請求項1~15のいずれかに記載の化合物。
- 有機エレクトロルミネッセンス素子用材料である請求項1~16のいずれかに記載の化合物。
- 有機エレクトロルミネッセンス素子用発光材料である請求項1~16のいずれかに記載の化合物。
- 有機エレクトロルミネッセンス素子用ドーピング材料である請求項1~16のいずれかに記載の化合物。
- 陰極と陽極の間に少なくとも発光層を含む1以上の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一層が、請求項1~16のいずれかに記載の化合物を単独もしくは混合物の成分として含有する有機エレクトロルミネッセンス素子。
- 前記少なくとも一層が、発光層である請求項20に記載の有機エレクトロルミネッセンス素子。
- 前記化合物がドーパント材料である請求項20又は21に記載の有機エレクトロルミネッセンス素子。
- 前記少なくとも一層が請求項1~16のいずれかに記載の化合物と、下記式(5)で表される化合物とを含有する請求項20に記載の有機エレクトロルミネッセンス素子。
R101~R108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原子数5~50の単環基、置換もしくは無置換の環形成原子数8~50の縮合環基、前記単環基と前記縮合環基の組合せから構成される基、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環形成炭素数3~50のシクロアルキル基、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、置換もしくは無置換のシリル基、ハロゲン原子、シアノ基から選ばれる基である。) - 前記式(5)において、Ar11、Ar12がそれぞれ置換もしくは無置換の環形成炭素数8~50の縮合環基である請求項23に記載の有機エレクトロルミネッセンス素子。
- 前記式(5)において、Ar11及びAr12の一方が置換もしくは無置換の環形成原子数5~50の単環基であり、他方が置換もしくは無置換の環形成原子数8~50の縮合環基である請求項23に記載の有機エレクトロルミネッセンス素子。
- 前記式(5)において、Ar12がナフチル基、フェナントリル基、ベンゾアントリル基、フルオレニル基又はジベンゾフラニル基であり、Ar11が無置換又は、単環基又は縮合環基が置換されたフェニル基である請求項25に記載の有機エレクトロルミネッセンス素子。
- 前記式(5)において、Ar12が置換もしくは無置換の環形成原子数8~50の縮合環基であり、Ar11が無置換のフェニル基である請求項25に記載の有機エレクトロルミネッセンス素子。
- 前記式(5)において、Ar11及びAr12が、それぞれ独立に、置換もしくは無置換の環形成原子数5~50の単環基である請求項23に記載の有機エレクトロルミネッセンス素子。
- 前記式(5)において、Ar11、Ar12がそれぞれ独立に置換もしくは無置換のフェニル基である請求項28に記載の有機エレクトロルミネッセンス素子。
- 前記式(5)において、Ar11が無置換のフェニル基であり、Ar12が、単環基又は縮合環基を置換基として有するフェニル基である請求項29に記載の有機エレクトロルミネッセンス素子。
- 前記式(5)において、Ar11、Ar12がそれぞれ独立に、単環基又は縮合環基を置換基として有するフェニル基である請求項29に記載の有機エレクトロルミネッセンス素子。
- 請求項20~31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搭載した電子機器。
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2015
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- 2015-09-18 KR KR1020167031760A patent/KR101780621B1/ko active IP Right Grant
- 2015-09-18 KR KR1020167001391A patent/KR101780605B1/ko active IP Right Grant
- 2015-09-18 JP JP2015560459A patent/JP6012889B2/ja active Active
- 2015-09-18 CN CN201580001476.XA patent/CN106170474B/zh active Active
- 2015-09-18 US US14/908,929 patent/US9902687B2/en active Active
- 2015-09-18 EP EP15823488.0A patent/EP3196187A4/en not_active Withdrawn
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- 2017-01-05 US US15/399,295 patent/US10118889B2/en active Active
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JP2019038798A (ja) * | 2017-08-22 | 2019-03-14 | 学校法人関西学院 | 多環芳香族化合物 |
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Also Published As
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US20190023648A1 (en) | 2019-01-24 |
JPWO2016042781A1 (ja) | 2017-04-27 |
KR102031678B1 (ko) | 2019-10-14 |
KR20160137647A (ko) | 2016-11-30 |
EP3196187A4 (en) | 2018-04-18 |
KR20170046107A (ko) | 2017-04-28 |
US10118889B2 (en) | 2018-11-06 |
KR101780621B1 (ko) | 2017-09-21 |
US9902687B2 (en) | 2018-02-27 |
KR20160140568A (ko) | 2016-12-07 |
CN106170474B (zh) | 2018-11-06 |
JP2017036293A (ja) | 2017-02-16 |
JP6012889B2 (ja) | 2016-10-25 |
US20170183291A1 (en) | 2017-06-29 |
CN106170474A (zh) | 2016-11-30 |
JP6338630B2 (ja) | 2018-06-06 |
EP3196187A1 (en) | 2017-07-26 |
US20170117469A1 (en) | 2017-04-27 |
KR101780605B1 (ko) | 2017-09-21 |
US10435350B2 (en) | 2019-10-08 |
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