WO2014203882A1 - アニリン誘導体、電荷輸送性ワニス及び有機エレクトロルミネッセンス素子 - Google Patents
アニリン誘導体、電荷輸送性ワニス及び有機エレクトロルミネッセンス素子 Download PDFInfo
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- WO2014203882A1 WO2014203882A1 PCT/JP2014/065999 JP2014065999W WO2014203882A1 WO 2014203882 A1 WO2014203882 A1 WO 2014203882A1 JP 2014065999 W JP2014065999 W JP 2014065999W WO 2014203882 A1 WO2014203882 A1 WO 2014203882A1
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- Prior art keywords
- group
- carbon atoms
- substituted
- formula
- aniline derivative
- Prior art date
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- 239000002966 varnish Substances 0.000 title claims description 69
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 154
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 60
- 125000005843 halogen group Chemical group 0.000 claims abstract description 51
- 125000003118 aryl group Chemical group 0.000 claims abstract description 37
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 28
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 18
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 14
- 125000003172 aldehyde group Chemical group 0.000 claims abstract description 13
- 125000002843 carboxylic acid group Chemical group 0.000 claims abstract description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- -1 amine compound Chemical class 0.000 claims description 151
- 150000001448 anilines Chemical class 0.000 claims description 67
- 239000010409 thin film Substances 0.000 claims description 40
- 239000002019 doping agent Substances 0.000 claims description 27
- 238000002347 injection Methods 0.000 claims description 25
- 239000007924 injection Substances 0.000 claims description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 20
- 239000003960 organic solvent Substances 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 11
- 230000005525 hole transport Effects 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000002577 pseudohalo group Chemical group 0.000 claims description 8
- 238000005401 electroluminescence Methods 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 3
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 3
- 239000010410 layer Substances 0.000 description 56
- 229910052741 iridium Inorganic materials 0.000 description 48
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 45
- 238000000034 method Methods 0.000 description 39
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 239000000758 substrate Substances 0.000 description 18
- 125000001153 fluoro group Chemical group F* 0.000 description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 229940125904 compound 1 Drugs 0.000 description 14
- 229910052731 fluorine Inorganic materials 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000000576 coating method Methods 0.000 description 11
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 11
- 239000012299 nitrogen atmosphere Substances 0.000 description 11
- 239000011964 heteropoly acid Substances 0.000 description 10
- 239000007983 Tris buffer Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 238000007789 sealing Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 5
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 5
- ONUFSRWQCKNVSL-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(2,3,4,5,6-pentafluorophenyl)benzene Chemical group FC1=C(F)C(F)=C(F)C(F)=C1C1=C(F)C(F)=C(F)C(F)=C1F ONUFSRWQCKNVSL-UHFFFAOYSA-N 0.000 description 4
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 4
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- UXKQNCDDHDBAPD-UHFFFAOYSA-N 4-n,4-n-diphenylbenzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 UXKQNCDDHDBAPD-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 150000004715 keto acids Chemical class 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000002861 polymer material Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 4
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 3
- YPIANBZIVBPMJS-UHFFFAOYSA-N 2-bromo-n,n-diphenylaniline Chemical compound BrC1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 YPIANBZIVBPMJS-UHFFFAOYSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000010304 firing Methods 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 239000011261 inert gas Substances 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
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000011733 molybdenum Substances 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
- 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 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- 239000010937 tungsten Substances 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 239000001211 (E)-4-phenylbut-3-en-2-one Substances 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- WFQFDAGQJUVDKP-UHFFFAOYSA-N 2,8-ditert-butyl-5,11-bis(4-tert-butylphenyl)-6,12-diphenyltetracene Chemical compound C1=CC(C(C)(C)C)=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC(=CC=C2C(C=2C=CC(=CC=2)C(C)(C)C)=C11)C(C)(C)C)=C(C=CC(=C2)C(C)(C)C)C2=C1C1=CC=CC=C1 WFQFDAGQJUVDKP-UHFFFAOYSA-N 0.000 description 2
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 2
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 2
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 2
- PKURFTDCIWJBDF-UHFFFAOYSA-N 2-hexylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCCCCC)=CC=C21 PKURFTDCIWJBDF-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- KIGVOJUDEQXKII-UHFFFAOYSA-N 4-bromo-n-(4-bromophenyl)-n-phenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC(Br)=CC=1)C1=CC=CC=C1 KIGVOJUDEQXKII-UHFFFAOYSA-N 0.000 description 2
- SNLFYGIUTYKKOE-UHFFFAOYSA-N 4-n,4-n-bis(4-aminophenyl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1N(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 SNLFYGIUTYKKOE-UHFFFAOYSA-N 0.000 description 2
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
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- 238000012546 transfer Methods 0.000 description 1
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- OYGYKEULCAINCL-UHFFFAOYSA-N triethoxy(hexadecyl)silane Chemical compound CCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC OYGYKEULCAINCL-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
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- ZRQAIBMAFLMIND-UHFFFAOYSA-N triethoxy(thiophen-2-yl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CS1 ZRQAIBMAFLMIND-UHFFFAOYSA-N 0.000 description 1
- QALDFNLNVLQDSP-UHFFFAOYSA-N triethoxy-(2,3,4,5,6-pentafluorophenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=C(F)C(F)=C(F)C(F)=C1F QALDFNLNVLQDSP-UHFFFAOYSA-N 0.000 description 1
- CUVIJHAPWYUQIV-UHFFFAOYSA-N triethoxy-[3-(1,1,1,2,3,3,3-heptafluoropropan-2-yloxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOC(F)(C(F)(F)F)C(F)(F)F CUVIJHAPWYUQIV-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
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- XSVXWCZFSFKRDO-UHFFFAOYSA-N triphenyl-(3-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=C(C=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XSVXWCZFSFKRDO-UHFFFAOYSA-N 0.000 description 1
- DETFWTCLAIIJRZ-UHFFFAOYSA-N triphenyl-(4-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DETFWTCLAIIJRZ-UHFFFAOYSA-N 0.000 description 1
- LNQMQGXHWZCRFZ-UHFFFAOYSA-N triphenyl-[4-(4-triphenylsilylphenyl)phenyl]silane Chemical group C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 LNQMQGXHWZCRFZ-UHFFFAOYSA-N 0.000 description 1
- HITRWHKLCHWBNZ-UHFFFAOYSA-N triphenyl-[4-(9-phenylfluoren-9-yl)phenyl]silane Chemical compound C1=CC=CC=C1C1(C=2C=CC(=CC=2)[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 HITRWHKLCHWBNZ-UHFFFAOYSA-N 0.000 description 1
- KIGXXTRUJYDDKP-UHFFFAOYSA-N triphenyl-[4-[4-(4-triphenylsilylphenyl)phenyl]phenyl]silane Chemical group C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 KIGXXTRUJYDDKP-UHFFFAOYSA-N 0.000 description 1
- RFDGVZHLJCKEPT-UHFFFAOYSA-N tris(2,4,6-trimethyl-3-pyridin-3-ylphenyl)borane Chemical compound CC1=C(B(C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C(C)=CC(C)=C1C1=CC=CN=C1 RFDGVZHLJCKEPT-UHFFFAOYSA-N 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—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
- C07C211/54—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 two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—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
- C07C211/57—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
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—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
- C07C211/57—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
- 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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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
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- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
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- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
Definitions
- the present invention relates to an aniline derivative, a charge transporting varnish, and an organic electroluminescence (hereinafter referred to as organic EL) element.
- a charge transporting thin film made of an organic compound is used as a light emitting layer or a charge injection layer.
- the hole injection layer is responsible for charge transfer between the anode and the hole transport layer or the light emitting layer, and plays an important function to achieve low voltage driving and high luminance of the organic EL element.
- the method of forming the hole injection layer is roughly divided into a dry process typified by vapor deposition and a wet process typified by spin coating. Compared with these processes, the wet process is flatter in a larger area. A highly efficient thin film can be produced efficiently. Therefore, at the present time when the area of the organic EL display is being increased, a hole injection layer that can be formed by a wet process is desired.
- the present inventors are applicable to various wet processes and have a charge transport property that provides a thin film that can realize excellent EL element characteristics when applied to a hole injection layer of an organic EL element.
- Compounds having good solubility in materials and organic solvents used therefor have been developed (see, for example, Patent Documents 1 to 4).
- the present invention like the technology of the above-mentioned patent document that has been developed so far, exhibits good solubility in an organic solvent and has excellent electrical characteristics when applied to a hole injection layer after being thinned. It is an object to provide a novel aniline derivative capable of realizing an EL element, a charge transporting varnish containing the aniline derivative, and an organic EL element.
- the present inventors show that a specific aniline derivative exhibits high solubility in an organic solvent, and from a varnish prepared by dissolving it in an organic solvent together with a dopant.
- the present invention has been completed by finding that the obtained thin film has high charge transporting properties, and that when the thin film is applied to a hole injection layer of an organic EL device, excellent electrical characteristics can be realized.
- R 2 to R 37 are a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms that may be substituted with Z 1 , an aryl group having 6 to 20 carbon atoms that may be substituted with Z 2 , or —OY 1 aniline derivative which is 2 groups.
- R 1 is an alkyl group having 1 to 20 carbon atoms which may be substituted with Z 1 , an aryl group having 6 to 20 carbon atoms which may be substituted with Z 2 , or a group represented by the formula (2) One or two aniline derivatives. 4).
- R 38 to R 55 are a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms that may be substituted with Z 1 , an aryl group having 6 to 20 carbon atoms that may be substituted with Z 2 , or —OY 4 aniline derivatives which are 2 groups.
- a charge transport material comprising any of the aniline derivatives of 1 to 5.
- a charge transporting varnish comprising the aniline derivative of any one of 1 to 5, a dopant and an organic solvent.
- a charge transporting thin film comprising the aniline derivative according to any one of 1 to 5.
- An electronic device comprising at least one charge transporting thin film of 10.8 or 9.
- An organic electroluminescent device comprising at least one charge-transporting thin film of 11.8 or 9. 12 11.
- 13. An amine compound represented by formula (3), an amine compound represented by formula (4), and an amine compound represented by formula (5) are reacted in the presence of a catalyst.
- a method for producing an aniline derivative. In the formula, R 1 to R 37 are the same as above. X represents a halogen atom or a pseudohalogen group.)
- An amine compound represented by formula (6), an amine compound represented by formula (7), and an amine compound represented by formula (8) are reacted in the presence of a catalyst.
- a method for producing an aniline derivative (In the formula, R 1 to R 37 are the same as above. X represents a halogen atom or a pseudohalogen group.) 15. A catalyst comprising an amine compound represented by formula (9), an amine compound represented by formula (4), an amine compound represented by formula (5), and an amine compound represented by formula (10) 4. A process for producing an aniline derivative according to 4, characterized by reacting in the presence. (In the formula, R 1 to R 55 are the same as above. X represents a halogen atom or a pseudohalogen group.)
- the aniline derivative of the present invention is easily soluble in an organic solvent, and the charge transporting varnish can be easily prepared by dissolving it in an organic solvent together with a dopant. Since the thin film produced from the charge transport varnish of the present invention exhibits high charge transport properties, it can be suitably used as a thin film for electronic devices including organic EL elements. In particular, by applying this thin film to a hole injection layer of an organic EL element, an organic EL element having excellent electrical characteristics can be obtained.
- the charge transporting varnish of the present invention can produce a thin film excellent in charge transporting properties with good reproducibility even when using various wet processes capable of forming a large area such as a spin coating method and a slit coating method, It can sufficiently cope with recent progress in the field of organic EL elements.
- aniline derivatives The aniline derivative according to the present invention is represented by the formula (1).
- R 1 is an alkyl group of Z 1 is 1 carbon atoms which may be ⁇ 20 substituted with an alkenyl group are optionally 2-20 carbon atoms substituted with Z 1, be substituted with Z 1 heteroaryl group or the formula which may alkynyl group having a carbon number of 2 - 20, Z 2 aryl groups are carbon atoms that may 6 to be 20 substituted, Z 2 is 1-2 carbon atoms which may be 20 substituted with ( The group represented by 2) is represented.
- R 2 to R 55 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, an aldehyde group, a hydroxy group, a thiol group, a carboxylic acid group, or a C 1-20 optionally substituted with Z 1 alkyl group
- an alkenyl group of Z 1 is optionally 2-20 carbon atoms substituted with, alkynyl groups which do 2-20 carbon atoms substituted with Z 1, carbon atoms, which may be substituted with Z 2
- Y 1 ⁇ Y 8 are each independently an alkyl group of Z 1 is 1 carbon atoms which may be ⁇ 20 substituted with an alkenyl group are optionally 2-20 carbon atoms substituted with Z 1, substituted by Z 1 is an alkynyl group which may having 2 to 20 carbon atoms have, heteroaryl aryl or Z 2 is optionally 2-20 carbon atoms substituted with Z 2 are carbon atoms 6 also be ⁇ 20 substituted by Represents.
- Z 1 is a halogen atom, a nitro group, a cyano group, an aldehyde group, a hydroxyl group, a thiol group, a sulfonic acid group, a carboxylic acid group, an aryl group, or Z 3 of Z 3 are carbon atoms that may 6 to be 20 substituted with Represents an optionally substituted heteroaryl group having 2 to 20 carbon atoms.
- Z 2 is a halogen atom, a nitro group, a cyano group, an aldehyde group, a hydroxyl group, a thiol group, a sulfonic acid group, a carboxylic acid group
- an alkyl group of Z 3 is - 1 carbon atoms and optionally 20 substituted with at Z 3
- An alkenyl group having 2 to 20 carbon atoms which may be substituted or an alkynyl group having 2 to 20 carbon atoms which may be substituted with Z 3 is represented.
- Z 3 represents a halogen atom, a nitro group, a cyano group, an aldehyde group, a hydroxyl group, a thiol group, a sulfonic acid group, or a carboxylic acid group.
- halogen atom examples include fluorine, chlorine, bromine and iodine atoms.
- the alkyl group having 1 to 20 carbon atoms may be linear, branched or cyclic. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, n-pentyl group, n-hexyl group, a linear or branched alkyl group having 1 to 20 carbon atoms such as n-heptyl group, n-octyl group, n-nonyl group, n-decyl group; cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclo Cyclic alkyl having 3 to 20 carbon atoms such as heptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclobuty
- the alkenyl group having 2 to 20 carbon atoms may be linear, branched or cyclic.
- Specific examples of the alkenyl group include ethenyl group, n-1-propenyl group, n-2-propenyl group, 1-methylethenyl group, n-1-butenyl group, n-2-butenyl group, and n-3-butenyl group.
- the alkynyl group having 2 to 20 carbon atoms may be linear, branched or cyclic.
- Specific examples of the alkynyl group include ethynyl group, n-1-propynyl group, n-2-propynyl group, n-1-butynyl group, n-2-butynyl group, n-3-butynyl group, 1-methyl- 2-propynyl group, n-1-pentynyl group, n-2-pentynyl group, n-3-pentynyl group, n-4-pentynyl group, 1-methyl-n-butynyl group, 2-methyl-n-butynyl group 3-methyl-n-butynyl group, 1,1-dimethyl-n-propynyl group, n-1-hexynyl group, n-1-decynyl group, n-1-pentadecynyl group,
- the carbon number of the alkyl group, alkenyl group and alkynyl group is preferably 12 or less, more preferably 6 or less, and even more preferably 4 or less.
- aryl group having 6 to 20 carbon atoms include phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group. Group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group and the like.
- heteroaryl group having 2 to 20 carbon atoms examples include 2-thienyl group, 3-thienyl group, 2-furanyl group, 3-furanyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 3-isoxazolyl group, 4-isoxazolyl group, 5-isoxazolyl group, 2-thiazolyl group, 4-thiazolyl group, 5-thiazolyl group, 3-isothiazolyl group, 4-isothiazolyl group, 5-isothiazolyl group, 2-imidazolyl group, Examples include 4-imidazolyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, and the like.
- the carbon number of the aryl group and heteroaryl group is preferably 14 or less, more preferably 10 or less, and even more preferably 6 or less.
- R 1 is an alkyl group having 1 to 20 carbon atoms which may be substituted with Z 1 , an aryl group having 6 to 20 carbon atoms which may be substituted with Z 2 , or a group represented by the formula (2) More preferably, an alkyl group having 1 to 10 carbon atoms which may be substituted with Z 1 , a phenyl group which may be substituted with Z 2 , or a group represented by formula (2).
- the group represented by is optimal.
- R 1 is a group represented by the formula (2), particularly R 38 to R 55 are a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may be substituted with Z 1 , or Z 2 substituted 1-6 carbon atoms which may be 20 aryl group, an alkoxy group of Z 1 is to 1 carbon atoms and optionally 20 substituted with (Y 2 are ⁇ 1 carbon atoms which may be substituted with Z 1 20 an aryl group of -OY 2 group is an alkyl group), or Z 2 optionally substituted good 6 to 20 carbon atoms aryloxy group (Y 2 is Z 2 are carbon atoms that may 6 to be 20 substituted with —OY 2 group is preferably a hydrogen atom, a fluorine atom, an alkyl group having 1 to 10 carbon atoms which may be substituted with Z 1 , or a phenyl group which may be substituted with Z 2. atoms, more preferred is also a phenyl group
- R 2 to R 37 are each a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms that may be substituted with Z 1 , or an aryl group having 6 to 20 carbon atoms that may be substituted with Z 2.
- an alkoxy group having 1 to 20 carbon atoms which may be substituted with Z 1 , or an aryloxy group having 6 to 20 carbon atoms which may be substituted with Z 2 is preferably a hydrogen atom, a fluorine atom or Z 1
- An alkyl group having 1 to 10 carbon atoms which may be substituted or a phenyl group which may be substituted with Z 2 is more preferred, and a phenyl group which may be substituted with a hydrogen atom, a fluorine atom or Z 2 is even more preferred.
- a hydrogen atom is optimal.
- R 2 to R 55 and Y 1 to Y 8 are an alkyl group, alkenyl group, alkynyl group, aryl group or heteroaryl group
- the substituent Z 1 may be substituted with a halogen atom or Z 3.
- a preferable aryl group having 6 to 20 carbon atoms is preferable, and a phenyl group which may be substituted with a halogen atom or Z 3 is more preferable, and it is optimal that it is not present (that is, unsubstituted).
- the substituent Z 2 is preferably a halogen atom or an alkyl group having 1 to 20 carbon atoms which may be substituted with Z 3 , and may be an alkyl group having 1 to 4 carbon atoms which may be substituted with a halogen atom or Z 3. It is most preferred that the group be absent and not present (ie, unsubstituted).
- Z 3 is preferably a halogen atom, more preferably fluorine, and optimally not present (that is, unsubstituted).
- the aniline derivative of the present invention comprises an amine compound represented by formula (3), an amine compound represented by formula (4), and an amine compound represented by formula (5) in the presence of a catalyst. (Scheme 1). (In the formula, each X independently represents a halogen atom or a pseudohalogen group. R 1 to R 37 are the same as above.)
- the aniline derivative of the present invention comprises an amine compound represented by formula (6), an amine compound represented by formula (7), and an amine compound represented by formula (8) in the presence of a catalyst. It can also be made to react (Scheme 2). (Wherein X and R 1 to R 37 are the same as above)
- the aniline derivative of the present invention in which R 1 is a group represented by formula (2) is represented by an amine compound represented by formula (9) and formula (4). It can be produced by reacting an amine compound, an amine compound represented by formula (5), and an amine compound represented by formula (10) in the presence of a catalyst (Scheme 3). (Wherein X and R 1 to R 55 are the same as above)
- the pseudohalogen group includes (fluoro) alkylsulfonyloxy groups such as methanesulfonyloxy group, trifluoromethanesulfonyloxy group, and nonafluorobutanesulfonyloxy group; aromatic sulfonyloxy groups such as benzenesulfonyloxy group and toluenesulfonyloxy group Groups and the like.
- Specific examples of the amine compound represented by the formula (3) include N-methyl-bis (4-aminophenyl) amine, N, N-bis (p-aminophenyl) aniline, and the like.
- Specific examples of the amine compound represented by the formula include N-methyl-bis (4-bromophenyl) amine, N, N-bis (p-bromophenyl) aniline, and the like, represented by the formula (9)
- Specific examples of the amine compound include tris (4-aminophenyl) amine and the like, but they are not limited to these.
- amine compounds represented by the formulas (4), (5) and (10) include 4′-bromo-N-phenyl- [1,1′-biphenyl] -4-amine
- amine compounds represented by the formulas (7) and (8) include N, N-diphenyl-p-phenylenediamine and the like, but they are not limited to these.
- the charge ratio between the amine compound represented by formula (9) and the amine compound represented by formula (4), (5), or (10) is 1 in terms of molar ratio. Although it can be as described above, about 1 to 1.2 is preferable.
- Examples of the catalyst used in the above reaction include copper catalysts such as copper chloride, copper bromide, copper iodide; tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ), bis (triphenylphosphine) dichloropalladium. (Pd (PPh 3 ) 2 Cl 2 ), bis (benzylideneacetone) palladium (Pd (dba) 2 ), tris (benzylideneacetone) dipalladium (Pd 2 (dba) 3 ), bis (tri-t-butylphosphine) Examples thereof include palladium catalysts such as palladium (Pd (Pt-Bu 3 ) 2 ). These catalysts may be used alone or in combination of two or more. These catalysts may be used together with a known appropriate ligand.
- copper catalysts such as copper chloride, copper bromide, copper iodide
- the amount of the catalyst used can be about 0.001 to 0.2 mol with respect to 1 mol of the amine compound represented by the formula (3), (6) or (9), but 0.005 to 0.005. About 05 mol is preferable.
- the amount used can be 0.1 to 5 equivalents relative to the metal complex used, but 1 to 4 equivalents are preferred.
- the above reaction may be performed in a solvent.
- the solvent is not particularly limited as long as it does not adversely influence the reaction.
- Specific examples of the solvent include aliphatic hydrocarbons (pentane, n-hexane, n-octane, n-decane, decalin, etc.), halogenated aliphatic hydrocarbons (chloroform, dichloromethane, dichloroethane, carbon tetrachloride, etc.) , Aromatic hydrocarbons (benzene, nitrobenzene, toluene, o-xylene, m-xylene, p-xylene, mesitylene, etc.), halogenated aromatic hydrocarbons (chlorobenzene, bromobenzene, o-dichlorobenzene, m-di) Chlorobenzene, p-dichlorobenzene, etc.), ethers (diethyl ether, diisoprop
- the reaction temperature may be appropriately set within the range from the melting point to the boiling point of the solvent to be used, but is preferably about 0 to 200 ° C, more preferably 20 to 150 ° C.
- the desired aniline derivative can be obtained by post-treatment according to a conventional method.
- the charge transporting varnish of the present invention contains a charge transporting substance composed of the aniline derivative represented by the formula (1) and an organic solvent. In order to improve the charge transporting ability and the like, a dopant is added as necessary. May be included.
- the dopant is not particularly limited as long as it is soluble in at least one solvent used for the varnish, and any of inorganic dopants and organic dopants can be used.
- Inorganic dopants include inorganic acids such as hydrogen chloride, sulfuric acid, nitric acid and phosphoric acid; aluminum chloride (III) (AlCl 3 ), titanium tetrachloride (IV) (TiCl 4 ), boron tribromide (BBr 3 ), Boron trifluoride ether complex (BF 3 ⁇ OEt 2 ), iron chloride (III) (FeCl 3 ), copper chloride (II) (CuCl 2 ), antimony pentachloride (V) (SbCl 5 ), antimony pentafluoride ( Metal halides such as V) (SbF 5 ), arsenic pentafluoride (V) (AsF 5 ), phosphorus pentafluoride (PF 5 ), tris (4-bromophenyl) aluminum hexachloroantimonate (TBPAH); Cl 2 , Br 2 , I 2 , ICl, ICl 3 , IBr,
- organic dopants include benzenesulfonic acid, tosylic acid, p-styrenesulfonic acid, 2-naphthalenesulfonic acid, 4-hydroxybenzenesulfonic acid, 5-sulfosalicylic acid, p-dodecylbenzenesulfonic acid, dihexylbenzenesulfonic acid, 2 , 5-dihexylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, 6,7-dibutyl-2-naphthalenesulfonic acid, dodecylnaphthalenesulfonic acid, 3-dodecyl-2-naphthalenesulfonic acid, hexylnaphthalenesulfonic acid, 4-hexyl-1 -Naphthalenesulfonic acid, octylnaphthalenesulfonic acid, 2-octyl-1-na
- Dioxane disulfonic acid compounds aryl sulfonic acid compounds described in WO 2006/025342, aryl sulfonic acid compounds described in WO 2009/096352, aryl sulfonic acid compounds such as polystyrene sulfonic acid; 10-camphor sulfonic acid, etc.
- Non-aryl sulfonic acid compounds; organic oxidants such as 7,7,8,8-tetracyanoquinodimethane (TCNQ), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) Can be mentioned.
- These inorganic and organic dopants may be used singly or in combination of two or more.
- heteropolyacids are preferred.
- heteropolyacid as a dopant, not only high hole acceptability from a transparent electrode typified by indium tin oxide (ITO) and indium zinc oxide (IZO) but also from a metal anode typified by aluminum A thin film having a high hole acceptability and excellent charge transportability can be obtained.
- the heteropolyacid typically has a structure in which a heteroatom is located at the center of a molecule, which is represented by a chemical structure of the Keggin type represented by the formula (B1) or the Dawson type represented by the formula (B2), and vanadium ( V), molybdenum (Mo), tungsten (W) and other oxoacids such as isopolyacids, and polyacids formed by condensation of oxoacids of different elements.
- oxo acids of different elements mainly include silicon (Si), phosphorus (P), and arsenic (As) oxo acids.
- heteropolyacids include phosphomolybdic acid, silicomolybdic acid, phosphotungstic acid, silicotungstic acid, and phosphotungstomolybdic acid. You may use these individually by 1 type or in combination of 2 or more types.
- the heteropolyacid used by this invention is available as a commercial item, and can also be synthesize
- the one type of heteropolyacid is preferably phosphotungstic acid or phosphomolybdic acid, and more preferably phosphotungstic acid.
- a dopant consists of 2 or more types of heteropolyacids, it is preferable that at least 1 is the phosphotungstic acid or phosphomolybdic acid among the 2 or more types of heteropolyacid, and it is more preferable that it is phosphotungstic acid.
- the heteropolyacid may be a commercially available product obtained from a structure represented by the general formula or a small number of elements, or a known synthesis method. As long as it is appropriately synthesized according to the above, it can be used in the present invention.
- phosphotungstic acid is generally represented by the chemical formula H 3 (PW 12 O 40 ) ⁇ nH 2 O
- phosphomolybdic acid is represented by the chemical formula H 3 (PMo 12 O 40 ) ⁇ nH 2 O.
- P phosphorus
- O oxygen
- W tungsten
- Mo molybdenum
- the mass of the heteropolyacid defined in the present invention is not the mass of pure phosphotungstic acid (phosphotungstic acid content) in the synthesized product or commercially available product, but a commercially available form and a known synthesis. In a form that can be isolated by the method, it means the total mass in a state containing hydration water and other impurities.
- An aryl sulfonic acid compound can also be used suitably.
- an aryl sulfonic acid compound represented by the formula (11) or (12) is preferable.
- a 1 represents —O— or —S—, preferably —O—.
- a 2 represents a naphthalene ring or an anthracene ring, and a naphthalene ring is preferable.
- a 3 represents a divalent to tetravalent perfluorobiphenyl group, p represents the number of bonds between A 1 and A 3, and is an integer satisfying 2 ⁇ p ⁇ 4, but A 3 is a divalent perfluorobiphenyl group. It is preferable that p is 2.
- q represents the number of sulfonic acid groups bonded to A 2 and is an integer satisfying 1 ⁇ q ⁇ 4, but 2 is preferable.
- a 4 to A 8 each independently represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, or 2 to 20 carbon atoms. Wherein at least three of A 4 to A 8 are halogen atoms.
- r represents the number of sulfonic acid groups bonded to the naphthalene ring, and is an integer satisfying 1 ⁇ r ⁇ 4, preferably 2 to 4, and more preferably 2.
- halogenated alkyl group having 1 to 20 carbon atoms examples include trifluoromethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2,2-pentafluoroethyl group, 3,3,3- Trifluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 1,1,2,2,3,3,3-heptafluoropropyl group, 4,4,4-trifluorobutyl group, 3,3,4,4,4-pentafluorobutyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, 1,1,2,2,3,3,4,4, Examples include 4-nonafluorobutyl group.
- halogenated alkenyl group having 2 to 20 carbon atoms examples include perfluorovinyl group, 1-perfluoropropenyl group, perfluoroallyl group, perfluorobutenyl group and the like.
- Other examples of the halogen atom and the alkyl group having 1 to 20 carbon atoms are the same as those described above, and the halogen atom is preferably a fluorine atom.
- a 4 to A 8 are a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, or a halogenated alkenyl group having 2 to 10 carbon atoms. And at least three of A 4 to A 8 are preferably fluorine atoms. And a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 5 carbon atoms, a fluorinated alkyl group having 1 to 5 carbon atoms, or a fluorinated alkenyl group having 2 to 5 carbon atoms, and A 4 to A 8.
- At least three of them are fluorine atoms. Further, they are a hydrogen atom, a fluorine atom, a cyano group, a perfluoroalkyl group having 1 to 5 carbon atoms or a perfluoroalkenyl group having 1 to 5 carbon atoms, and A 4 , A 5 and A 8 are fluorine atoms. Even more preferred.
- the perfluoroalkyl group is a group in which all hydrogen atoms of the alkyl group are substituted with fluorine atoms
- the perfluoroalkenyl group is a group in which all hydrogen atoms of the alkenyl group are substituted with fluorine atoms.
- aryl sulfonic acid compounds suitable as other dopants in the present invention are listed, but are not limited thereto.
- charge transporting material 1 comprising the aniline derivative of the invention is generally in the range of about 0.01 to 50.
- the heteropolyacid when used as a dopant, is about 0.5 to 30.0, preferably about 1.0 to 20.0, more preferably 2.
- Charge transport that provides high brightness when used in an organic EL device by setting it to about 0 to 15.0, more preferably about 3.0 to 12.0, and still more preferably about 4.0 to 11.0. Can be obtained with good reproducibility.
- the aryl sulfonic acid compound when used as a dopant, is 0.05 to 15.0, preferably 0.10 to 10.0, more preferably, in molar ratio to the charge transporting material 1. Is 0.25 to 7.0, more preferably 0.50 to 5.0, and even more preferably 0.75 to 3.0, so that charge transport giving high luminance when used in an organic EL device Can be obtained with good reproducibility.
- the charge transporting varnish of the present invention may contain an organosilane compound.
- the hole injection ability to the layer laminated so as to be in contact with the hole injection layer on the side opposite to the anode, such as the hole transport layer and the light emitting layer can be increased, and as a result, higher Electric characteristics can be realized.
- organosilane compound examples include dialkoxysilane compounds, trialkoxysilane compounds, and tetraalkoxysilane compounds. You may use these individually by 1 type or in combination of 2 or more types.
- the organosilane compound is preferably a dialkoxysilane compound or a trialkoxysilane compound, more preferably a trialkoxysilane compound.
- dialkoxysilane compounds examples include those represented by the formulas (13) to (15).
- SiR ' 2 (OR) 2 (13) SiR '(OR) 3
- Si (OR) 4 (15)
- R each independently represents an alkyl group of Z 4 is 1 carbon atoms which may be ⁇ 20 substituted with an alkenyl group Z 4 is 1-2 carbon atoms which may be 20 substituted with substituted with Z 4 which may be an alkynyl group having 2 to 20 carbon atoms, a heteroaryl group aryl or Z 5 carbon atoms which may be substituted with 2-20 of Z 5 which do 6 to carbon atoms which may be 20 substituted with To express.
- Z 4 represents a heteroaryl group of a halogen atom, Z 8 of which do 6 to carbon atoms which may be 20 substituted with an aryl group, or Z 8 are optionally 2-20 carbon atoms substituted with.
- Z 5 represents a halogen atom, optionally substituted alkenyl group, or Z 8 alkyl groups, which do 2-20 carbon atoms substituted with Z 8 of to 1 carbon atoms which may be ⁇ 20 substituted by Z 8 Or an alkynyl group having 2 to 20 carbon atoms.
- Z 6 represents a halogen atom, an aryl group of carbon atoms which may be have 6 to 20 substituted with Z 8, heteroaryl group which optionally 2-20 carbon atoms substituted with Z 8, epoxycyclohexyl group, a glycidoxy group Methacryloxy group, acryloxy group, ureido group (—NHCONH 2 ), thiol group, isocyanate group (—NCO), amino group, —NHY 9 group or —NY 10 Y 11 group.
- Z 7 is halogen atom, Z 8 substituted by 1 carbon atoms which may be 1-20 alkyl group, an alkenyl group which 1-2 carbon atoms which may be 20 substituted with Z 8, it is substituted with Z 8 C2-C20 alkynyl group, epoxycyclohexyl group, glycidoxy group, methacryloxy group, acryloxy group, ureido group (—NHCONH 2 ), thiol group, isocyanate group (—NCO), amino group, —NHY 9 group or —Ny represents a Y 10 Y 11 group.
- Y 9 ⁇ Y 11 each independently represent an alkyl group which 1 carbon atoms which may be ⁇ 20 substituted by Z 8, an alkenyl group is 2 carbon atoms which may be ⁇ 20 substituted by Z 8, substituted by Z 8 is an alkynyl group of 2 carbon atoms which may be to 20, heteroaryl group of the aryl group or Z 8 is 2 carbon atoms which may be ⁇ 20 substituted with which do 6 to carbon atoms which may be 20 substituted with Z 8 Represents.
- Z 8 represents a halogen atom, an amino group, a nitro group, a cyano group or a thiol group.
- a halogen atom an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and carbon
- the heteroaryl group of 2 to 20 include those similar to the above.
- the carbon number of the alkyl group, alkenyl group, and alkynyl group is preferably 10 or less, more preferably 6 or less, and even more preferably 4 or less.
- the carbon number of the aryl group and heteroaryl group is preferably 14 or less, more preferably 10 or less, and even more preferably 6 or less.
- R is preferably an alkyl group having 1 to 20 carbon atoms which may be substituted with Z 4 , an alkenyl group having 2 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms which may be substituted with Z 5.
- alkyl group of Z 4 is 1 carbon atoms which may be ⁇ replaced by 6, more preferably an alkenyl group or a phenyl group optionally substituted by Z 5 2 to 6 carbon atoms, optionally substituted by Z 4
- Further preferred is an alkyl group having 1 to 4 carbon atoms or a phenyl group which may be substituted with Z 5 , and a methyl group or ethyl group which may be substituted with Z 4 is more preferred.
- an aryl group which may having 6 to 20 carbon atoms substituted with an alkyl group or Z 7 of is 1 carbon atoms which may be ⁇ 20 substituted with Z 6, it is substituted with Z 6 More preferably an alkyl group having 1 to 10 carbon atoms which may be substituted or an aryl group having 6 to 14 carbon atoms which may be substituted with Z 7 , and an alkyl having 1 to 6 carbon atoms which may be substituted with Z 6 more preferably more aryl group having to 10 6 carbon atoms which may be substituted with a group or Z 7, optionally substituted by an alkyl group or Z 7 of is 1 carbon atoms which may be 1-4 substituted with Z 6 A good phenyl group is more preferred.
- a plurality of R may be all the same or different, and a plurality of R ′ may all be the same or different.
- Z 4 is preferably a halogen atom or an aryl group having 6 to 20 carbon atoms which may be substituted with Z 8 , more preferably a fluorine atom or a phenyl group which may be substituted with Z 8 , and not present ( That is, it is optimal to be unsubstituted.
- a halogen atom or an alkyl group Z 8 are optionally 1-6 carbon atoms which may be 20 substituted with preferably an alkyl group having a fluorine atom or Z 8 is 1 carbon atoms which may be ⁇ 10 substituted by Is more preferred and not present (ie, unsubstituted).
- the Z 6, a halogen atom, a phenyl group which may be substituted with Z 8, which may be substituted furanyl group Z 8, epoxycyclohexyl group, a glycidoxy group, a methacryloxy group, an acryloxy group, a ureido group, thiol group, isocyanate group, amino group, good diphenylamino group optionally substituted with an optionally substituted phenylamino group or Z 8 in Z 8 preferably, the more preferred is a halogen atom, no fluorine atom or presence ( That is, it is even more preferable that it is unsubstituted.
- Z 7 halogen atom, Z alkyl group having 1 carbon atoms which may be 20 substituted by 8, which may be substituted furanyl group Z 8, epoxycyclohexyl group, a glycidoxy group, a methacryloxy group, acryloxy group, ureido group, a thiol group, isocyanate group, amino group, good diphenylamino group optionally substituted by a phenyl amino group, or Z 8 may be substituted with Z 8 preferably, more preferably a halogen atom, fluorine Even more preferred is an atom or absence (ie, unsubstituted).
- Z 8 is preferably a halogen atom, more preferably a fluorine atom or not (ie, unsubstituted).
- dialkoxysilane compounds include dimethyldimethoxysilane, dimethyldiethoxysilane, methylethyldimethoxysilane, diethyldimethoxysilane, diethyldiethoxysilane, methylpropyldimethoxysilane, methylpropyldiethoxysilane, diisopropyldimethoxysilane, and phenylmethyl.
- Dimethoxysilane vinylmethyldimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3- (3,4-epoxycyclohexyl) ethylmethyldimethoxysilane, 3-methacryloxy Propylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-mercaptopropylmethyldimethoxysilane, ⁇ -aminopropylmethyl Diethoxy silane, N- (2- aminoethyl) aminopropyl methyl dimethoxy silane, 3,3,3-trifluoropropyl methyl dimethoxy silane, and the like.
- trialkoxysilane compounds include methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, propyltrimethoxysilane, propyltriethoxysilane, butyltrimethoxysilane, butyltriethoxysilane, Pentyltrimethoxysilane, pentyltriethoxysilane, heptyltrimethoxysilane, heptyltriethoxysilane, octyltrimethoxysilane, octyltriethoxysilane, dodecyltrimethoxysilane, dodecyltriethoxysilane, hexadecyltrimethoxysilane, hexadecyltriethoxy Silane, octadecyltrimethoxysilane, o
- tetraalkoxysilane compound examples include tetramethoxysilane, tetraethoxysilane, and tetrapropoxysilane.
- the content thereof is usually based on the total mass of the charge transporting material and the dopant in consideration of maintaining the high charge transporting property of the obtained thin film.
- it is about 0.1 to 50% by mass, it is laminated so as to suppress a decrease in charge transportability of the obtained thin film and to be in contact with the hole injection layer on the side opposite to the anode such as a hole transport layer and a light emitting layer.
- it is preferably about 0.5 to 40% by mass, more preferably about 0.8 to 30% by mass, and still more preferably about 1 to 20% by mass. .
- the charge transport varnish of the present invention may use other known charge transport materials in addition to the above-described charge transport materials composed of aniline derivatives.
- organic solvent used when preparing the charge transporting varnish a highly soluble solvent that can dissolve the charge transporting substance and the dopant satisfactorily can be used.
- Examples of such highly soluble solvents include organic solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, and diethylene glycol monomethyl ether. Can be used. These solvents can be used singly or in combination of two or more, and the amount used can be 5 to 100% by mass with respect to the total solvent used in the varnish.
- charge transporting substance and the dopant are preferably either completely dissolved or uniformly dispersed in the solvent, and more preferably completely dissolved.
- the varnish has a viscosity of 10 to 200 mPa ⁇ s, particularly 35 to 150 mPa ⁇ s at 25 ° C., and a boiling point of 50 to 300 ° C., particularly 150 to 250 ° C. at normal pressure (atmospheric pressure).
- a viscosity of 10 to 200 mPa ⁇ s particularly 35 to 150 mPa ⁇ s at 25 ° C.
- a boiling point of 50 to 300 ° C., particularly 150 to 250 ° C. at normal pressure (atmospheric pressure).
- the high-viscosity organic solvent is not particularly limited.
- cyclohexanol ethylene glycol, ethylene glycol diglycidyl ether, 1,3-octylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol 1,3-butanediol, 2,3-butanediol, 1,4-butanediol, propylene glycol, hexylene glycol and the like.
- These solvents may be used alone or in combination of two or more.
- the addition ratio of the high-viscosity organic solvent to the entire solvent used in the varnish of the present invention is preferably in the range where no solid precipitates, and the addition ratio is preferably 5 to 80% by mass as long as no solid precipitates.
- the other solvent is preferably 1 to 90% by mass with respect to the total solvent used in the varnish, More preferably, it can be mixed at a ratio of 1 to 50% by mass.
- solvents examples include propylene glycol monomethyl ether, ethylene glycol monobutyl ether, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, dipropylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, and diethylene glycol.
- solvents include, but are not limited to, monoethyl ether, diacetone alcohol, ⁇ -butyrolactone, ethyl lactate, and n-hexyl acetate. These solvents can be used alone or in combination of two or more.
- the viscosity of the varnish of the present invention is appropriately set according to the thickness of the thin film to be produced and the solid content concentration, but is usually 1 to 50 mPa ⁇ s at 25 ° C.
- the solid content concentration of the charge transporting varnish in the present invention is appropriately set in consideration of the viscosity and surface tension of the varnish, the thickness of the thin film to be produced, etc., but is usually from 0.1 to 10 In consideration of improving the coatability of the varnish, it is preferably 0.5 to 5.0% by mass, more preferably 1.0 to 3.0% by mass.
- the charge transporting thin film can be formed on the base material by applying the above charge transporting varnish onto the base material and baking it.
- the coating method of the varnish is not particularly limited, and examples thereof include a dipping method, a spin coating method, a transfer printing method, a roll coating method, a brush coating, an ink jet method, a spray method, and a slit coating method. Accordingly, it is preferable to adjust the viscosity and surface tension of the varnish.
- the firing atmosphere is not particularly limited, and a thin film having a uniform film formation surface and a high charge transport property not only in the air atmosphere but also in an inert gas such as nitrogen or in a vacuum. Obtainable.
- the firing temperature is appropriately set within a range of about 100 to 260 ° C. in consideration of the use of the obtained thin film, the degree of charge transportability imparted to the obtained thin film, and the like.
- the temperature is preferably about 140 to 250 ° C, more preferably about 145 to 240 ° C.
- two or more temperature changes may be applied for the purpose of developing a higher uniform film forming property or causing the reaction to proceed on the substrate.
- the heating may be performed using an appropriate device such as a hot plate or an oven.
- the thickness of the charge transporting thin film is not particularly limited, but is preferably 5 to 200 nm when used as a hole injection layer in an organic EL device.
- a method of changing the film thickness there are methods such as changing the solid content concentration in the varnish and changing the amount of the solution on the substrate during coating.
- Organic EL device examples of materials used and methods for producing an OLED element using the charge transporting varnish of the present invention include, but are not limited to, the following.
- the electrode substrate to be used is preferably cleaned in advance by liquid cleaning with a detergent, alcohol, pure water or the like.
- the anode substrate is subjected to surface treatment such as UV ozone treatment or oxygen-plasma treatment immediately before use. It is preferable.
- the surface treatment may not be performed.
- An example of a method for producing an OLED element having a hole injection layer made of a thin film obtained from the charge transporting varnish of the present invention is as follows.
- the charge transporting varnish of the present invention is applied to the anode substrate and baked to form a hole injection layer on the electrode.
- This is introduced into a vacuum deposition apparatus, and a hole transport layer, a light emitting layer, an electron transport layer, an electron transport layer / hole block layer, and a cathode metal are sequentially deposited to form an OLED element.
- an electron blocking layer may be provided between the light emitting layer and the hole transport layer.
- anode material examples include transparent electrodes typified by indium tin oxide (ITO) and indium zinc oxide (IZO), metal anodes typified by aluminum, alloys thereof, and the like. What performed the chemical conversion process is preferable. Polythiophene derivatives and polyaniline derivatives having high charge transporting properties can also be used.
- metals constituting the metal anode include scandium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, gallium, yttrium, zirconium, niobium, molybdenum, ruthenium, rhodium, palladium, and cadmium.
- Materials for forming the hole transport layer include (triphenylamine) dimer derivatives, [(triphenylamine) dimer] spirodimers, N, N′-bis (naphthalen-1-yl) -N, N′-bis (Phenyl) -benzidine ( ⁇ -NPD), N, N′-bis (naphthalen-2-yl) -N, N′-bis (phenyl) -benzidine, N, N′-bis (3-methylphenyl)- N, N′-bis (phenyl) -benzidine, N, N′-bis (3-methylphenyl) -N, N′-bis (phenyl) -9,9-spirobifluorene, N, N′-bis ( Naphthalen-1-yl) -N, N′-bis (phenyl) -9,9-spirobifluorene, N, N′-bis (3-methylphenyl) -N, N′-bis (phenyl) -9,9-s
- Materials for forming the light emitting layer include tris (8-quinolinolato) aluminum (III) (Alq 3 ), bis (8-quinolinolato) zinc (II) (Znq 2 ), bis (2-methyl-8-quinolinolato) ( p-phenylphenolate) aluminum (III) (BAlq), 4,4'-bis (2,2-diphenylvinyl) biphenyl, 9,10-di (naphthalen-2-yl) anthracene, 2-t-butyl- 9,10-di (naphthalen-2-yl) anthracene, 2,7-bis [9,9-di (4-methylphenyl) -fluoren-2-yl] -9,9-di (4-methylphenyl) Fluorene, 2-methyl-9,10-bis (naphthalen-2-yl) anthracene, 2- (9,9-spirobifluoren-2-yl) -9,9-spirobifluorene
- Materials for forming the electron injection layer include lithium oxide (Li 2 O), magnesium oxide (MgO), alumina (Al 2 O 3 ), lithium fluoride (LiF), sodium fluoride (NaF), magnesium fluoride ( MgF 2 ), cesium fluoride (CsF), strontium fluoride (SrF 2 ), molybdenum trioxide (MoO 3 ), aluminum, Li (acac), lithium acetate, lithium benzoate and the like.
- cathode material examples include aluminum, magnesium-silver alloy, aluminum-lithium alloy, lithium, sodium, potassium, cesium and the like.
- Examples of the material for forming the electron block layer include tris (phenylpyrazole) iridium.
- the method for producing a PLED element using the charge transporting varnish of the present invention is not particularly limited, and examples thereof include the following methods.
- the hole transport polymer layer and the light emitting polymer layer are sequentially formed.
- a PLED element having a charge transporting thin film formed by the charge transporting varnish of the invention can be produced.
- the charge transporting varnish of the present invention is applied on the anode substrate to prepare a hole injection layer by the above method, and a hole transporting polymer layer and a light emitting polymer layer are sequentially formed thereon. Then, a cathode electrode is vapor-deposited to obtain a PLED element.
- the same materials as those used in the production of the OLED element can be used, and the same cleaning treatment and surface treatment can be performed.
- a hole transporting polymer material or a light emitting polymer material, or a material in which a dopant is added to these materials are added and dissolved.
- coating on a positive hole injection layer or a positive hole transportable polymer layer, and baking each is mentioned.
- Examples of the light-emitting polymer material include polyfluorene derivatives such as poly (9,9-dialkylfluorene) (PDAF), poly (2-methoxy-5- (2′-ethylhexoxy) -1,4-phenylenevinylene) (MEH). -PPV) and the like, polythiophene derivatives such as poly (3-alkylthiophene) (PAT), polyvinylcarbazole (PVCz) and the like.
- PDAF poly (9,9-dialkylfluorene)
- MEH 2-methoxy-5- (2′-ethylhexoxy) -1,4-phenylenevinylene
- PVT polythiophene derivatives
- PVCz polyvinylcarbazole
- Examples of the solvent include toluene, xylene, chloroform and the like, and examples of the dissolution or uniform dispersion method include stirring, heating and stirring, and ultrasonic dispersion.
- the coating method is not particularly limited, and examples include an inkjet method, a spray method, a dip method, a spin coating method, a transfer printing method, a roll coating method, and a brush coating.
- the application is preferably performed under an inert gas such as nitrogen or argon.
- the deposited film obtained from the aniline derivative of the present invention is also excellent in charge transporting properties. May be used.
- the resulting residue was completely dissolved in 1,4-dioxane (12.5 g) heated to 80 ° C. Dissolved. Thereto was added 0.14 g of activated carbon, and the mixture was stirred for 30 minutes. After completion of the stirring, the activated carbon was removed by hot filtration, and the organic solvent was distilled off from the obtained filtrate under reduced pressure.
- the obtained residue was dissolved in 25 g of toluene, column chromatography was performed, and the presence or absence of the target product was confirmed by a thin layer chromatography (TLC) method or the like to fractionate a fraction containing the target product.
- TLC thin layer chromatography
- Example 2-1 0.062 g of aniline derivative 1 and 0.309 g of phosphotungstic acid (PTA) were dissolved in 4 g of 1,3-dimethyl-2-imidazolidinone (DMI) under a nitrogen atmosphere. To the resulting solution, 6 g of cyclohexanol (CHA) and 2 g of propylene glycol (PG) were added and stirred to prepare a charge transporting varnish.
- DMI 1,3-dimethyl-2-imidazolidinone
- Example 2-2 A charge transporting varnish was prepared in the same manner as in Example 2-1, except that the amounts of aniline derivative 1 and PTA used were 0.053 g and 0.318 g, respectively.
- Example 2-3 0.062 g of aniline derivative 2 and 0.309 g of PTA were dissolved in 4 g of DMI under a nitrogen atmosphere. To the obtained solution, 6 g of CHA and 2 g of PG were added and stirred to prepare a charge transporting varnish.
- Example 2-4 A charge transporting varnish was prepared in the same manner as in Example 2-3, except that the amounts of aniline derivative 2 and PTA used were 0.053 g and 0.318 g, respectively.
- Example 2-5 0.062 g of aniline derivative 3 and 0.309 g of PTA were dissolved in 4 g of DMI under a nitrogen atmosphere. To the obtained solution, 6 g of CHA and 2 g of PG were added and stirred to prepare a charge transporting varnish.
- Example 2-6 A charge transporting varnish was prepared in the same manner as in Example 2-5, except that the amounts of aniline derivative 3 and PTA used were 0.053 g and 0.318 g, respectively.
- Example 3-1 0.083 g of aniline derivative 1 and 0.161 g of aryl sulfonic acid compound 1 were dissolved in 4 g of DMI under a nitrogen atmosphere. To the obtained solution, 6 g of CHA and 2 g of PG were added and stirred to prepare a charge transporting varnish.
- Example 3-2 0.088 g of aniline derivative 2 and 0.157 g of aryl sulfonic acid compound 1 were dissolved in 4 g of DMI under a nitrogen atmosphere. To the obtained solution, 6 g of CHA and 2 g of PG were added and stirred to prepare a charge transporting varnish.
- Example 3-3 A charge transporting varnish was prepared in the same manner as in Example 3-2 except that the amounts of aniline derivative 2 and arylsulfonic acid compound 1 used were 0.073 g and 0.172 g, respectively.
- Example 3-4 0.082 g of aniline derivative 3 and 0.163 g of aryl sulfonic acid compound 1 were dissolved in 4 g of DMI under a nitrogen atmosphere. To the obtained solution, 6 g of CHA and 2 g of PG were added and stirred to prepare a charge transporting varnish.
- Example 3-5 A charge transporting varnish was prepared in the same manner as in Example 3-4, except that the amounts of aniline derivative 3 and arylsulfonic acid compound 1 used were 0.067 g and 0.178 g, respectively.
- Example 4-1 An aniline derivative 1 (0.107 g) and an aryl sulfonic acid compound 1 (0.138 g) were dissolved in 4 g of DMI under a nitrogen atmosphere. To the resulting solution, 6 g of CHA and 2 g of PG were added and stirred, and 0.016 g of 3,3,3-trifluoropropyltrimethoxysilane and 0.008 g of phenyltrimethoxysilane were further added thereto, and the mixture was further stirred to obtain a charge transport property. A varnish was prepared.
- Example 4-2 A charge transporting varnish was prepared in the same manner as in Example 4-1, except that the amounts of aniline derivative 1 and arylsulfonic acid compound 1 used were 0.083 g and 0.161 g, respectively.
- Example 4-3 0.112 g of aniline derivative 2 and 0.133 g of aryl sulfonic acid compound 1 were dissolved in 4 g of DMI under a nitrogen atmosphere. To the resulting solution, 6 g of CHA and 2 g of PG were added and stirred, and 0.016 g of 3,3,3-trifluoropropyltrimethoxysilane and 0.008 g of phenyltrimethoxysilane were further added thereto, and the mixture was further stirred to obtain a charge transport property. A varnish was prepared.
- Example 4-4 and 4-5 Except that the amounts used of the aniline derivative 2 and the aryl sulfonic acid compound 1 were 0.088 g and 0.157 g (Example 4-4), 0.073 g and 0.172 g (Example 4-5), respectively.
- a charge transporting varnish was prepared in the same manner as in Example 4-3.
- Example 4-6 0.105 g of aniline derivative 3 and 0.140 g of aryl sulfonic acid compound 1 were dissolved in 4 g of DMI under a nitrogen atmosphere. To the resulting solution, 6 g of CHA and 2 g of PG were added and stirred, and 0.016 g of 3,3,3-trifluoropropyltrimethoxysilane and 0.008 g of phenyltrimethoxysilane were further added thereto, and the mixture was further stirred to obtain a charge transport property. A varnish was prepared.
- Example 4-7 and 4-8 Except that the amounts of aniline derivative 3 and arylsulfonic acid compound 1 used were 0.082 g and 0.163 g (Example 4-7), 0.067 g and 0.178 g (Example 4-8), respectively.
- a charge transporting varnish was prepared in the same manner as in Example 4-6.
- Example 5 The varnishes obtained in Examples 2-1 to 4-8 were each applied to an ITO substrate using a spin coater, dried at 50 ° C. for 5 minutes, and further baked at 230 ° C. for 15 minutes in an air atmosphere. A uniform thin film of 30 nm was formed on the ITO substrate.
- ITO indium tin oxide
- a water catching agent manufactured by Dynic Co., Ltd., HD-071010W-40 was placed in a sealing substrate together with the organic EL element.
- the bonded sealing substrate was irradiated with UV light (wavelength: 365 nm, irradiation amount: 6,000 mJ / cm 2 ), and then annealed at 80 ° C. for 1 hour to cure the adhesive.
- Table 1 shows the results of the devices manufactured using the varnishes of Examples 2-1 to 2-6
- Table 2 shows the results of the devices manufactured using the varnishes of Examples 3-1 to 3-6
- Table 3 shows the results of the devices manufactured using 4-1 to 4-8 varnishes.
- the organic EL device provided with the charge transporting thin film obtained from the charge transporting varnish according to the present invention was excellent in durability.
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Abstract
Description
1.式(1)で表されることを特徴とするアニリン誘導体。
Y1~Y8は、それぞれ独立にZ1で置換されていてもよい炭素数1~20のアルキル基、Z1で置換されていてもよい炭素数2~20のアルケニル基、Z1で置換されていてもよい炭素数2~20のアルキニル基、Z2で置換されていてもよい炭素数6~20のアリール基又はZ2で置換されていてもよい炭素数2~20のヘテロアリール基を表し、
Z1は、ハロゲン原子、ニトロ基、シアノ基、アルデヒド基、水酸基、チオール基、スルホン酸基、カルボン酸基、Z3で置換されていてもよい炭素数6~20のアリール基又はZ3で置換されていてもよい炭素数2~20のヘテロアリール基を表し、
Z2は、ハロゲン原子、ニトロ基、シアノ基、アルデヒド基、水酸基、チオール基、スルホン酸基、カルボン酸基、Z3で置換されていてもよい炭素数1~20のアルキル基、Z3で置換されていてもよい炭素数2~20のアルケニル基又はZ3で置換されていてもよい炭素数2~20のアルキニル基を表し、
Z3は、ハロゲン原子、ニトロ基、シアノ基、アルデヒド基、水酸基、チオール基、スルホン酸基又はカルボン酸基を表す。)
2.R2~R37が水素原子、ハロゲン原子、Z1で置換されていてもよい炭素数1~20のアルキル基、Z2で置換されていてもよい炭素数6~20のアリール基又は-OY2基である1のアニリン誘導体。
3.R1が、Z1で置換されていてもよい炭素数1~20のアルキル基、Z2で置換されていてもよい炭素数6~20のアリール基又は式(2)で表される基である1又は2のアニリン誘導体。
4.R1が式(2)で表される基である3のアニリン誘導体。
5.R38~R55が水素原子、ハロゲン原子、Z1で置換されていてもよい炭素数1~20のアルキル基、Z2で置換されていてもよい炭素数6~20のアリール基又は-OY2基である4のアニリン誘導体。
6.1~5のいずれかのアニリン誘導体からなる電荷輸送性物質。
7.1~5のいずれかのアニリン誘導体、ドーパント及び有機溶媒を含む電荷輸送性ワニス。
8.7の電荷輸送性ワニスを用いて作製される電荷輸送性薄膜。
9.1~5のいずれかのアニリン誘導体を含む電荷輸送性薄膜。
10.8又は9の電荷輸送性薄膜を少なくとも1層備える電子デバイス。
11.8又は9の電荷輸送性薄膜を少なくとも1層備える有機エレクトロルミネッセンス素子。
12.前記電荷輸送性薄膜が、正孔注入層又は正孔輸送層である11の有機エレクトロルミネッセンス素子。
13.式(3)で表されるアミン化合物と、式(4)で表されるアミン化合物と、式(5)で表されるアミン化合物とを、触媒存在下で反応させることを特徴とする1のアニリン誘導体の製造方法。
14.式(6)で表されるアミン化合物と、式(7)で表されるアミン化合物と、式(8)で表されるアミン化合物とを、触媒存在下で反応させることを特徴とする1のアニリン誘導体の製造方法。
15.式(9)で表されるアミン化合物と、式(4)で表されるアミン化合物と、式(5)で表されるアミン化合物と、式(10)で表されるアミン化合物とを、触媒存在下で反応させることを特徴とする4のアニリン誘導体の製造方法。
本発明の電荷輸送性ワニスから作製した薄膜は高い電荷輸送性を示すため、有機EL素子をはじめとした電子デバイス用薄膜として好適に用いることができる。特に、この薄膜を有機EL素子の正孔注入層に適用することで、電気特性に優れた有機EL素子を得ることができる。
また、本発明の電荷輸送性ワニスは、スピンコート法やスリットコート法等、大面積に成膜可能な各種ウェットプロセスを用いた場合でも電荷輸送性に優れた薄膜を再現性よく製造できるため、近年の有機EL素子の分野における進展にも十分対応できる。
また、置換基Z2は、ハロゲン原子又はZ3で置換されていてもよい炭素数1~20のアルキル基が好ましく、ハロゲン原子又はZ3で置換されていてもよい炭素数1~4のアルキル基がより好ましく、存在しないこと(すなわち、非置換であること)が最適である。
そして、Z3は、ハロゲン原子が好ましく、フッ素がより好ましく、存在しないこと(すなわち、非置換であること)が最適である。
本発明のアニリン誘導体は、式(3)で表されるアミン化合物と、式(4)で表されるアミン化合物と、式(5)で表されるアミン化合物とを、触媒存在下で反応させて製造することができる(スキーム1)。
また、配位子を用いる場合、その使用量は、使用する金属錯体に対し0.1~5当量とすることができるが、1~4当量が好適である。
反応終了後は、常法にしたがって後処理をし、目的とするアニリン誘導体を得ることができる。
本発明の電荷輸送性ワニスは、式(1)で表されるアニリン誘導体からなる電荷輸送性物質と有機溶媒とを含むものであるが、電荷輸送能等を向上させるために、必要に応じてドーパントを含んでいてもよい。
その他、ハロゲン原子、炭素数1~20のアルキル基の例としては上記と同様のものが挙げられるが、ハロゲン原子としては、フッ素原子が好ましい。
SiR'2(OR)2 (13)
SiR'(OR)3 (14)
Si(OR)4 (15)
Z5は、ハロゲン原子、Z8で置換されていてもよい炭素数1~20のアルキル基、Z8で置換されていてもよい炭素数2~20のアルケニル基又はZ8で置換されていてもよい炭素数2~20のアルキニル基を表す。
Z6は、ハロゲン原子、Z8で置換されていてもよい炭素数6~20のアリール基、Z8で置換されていてもよい炭素数2~20のヘテロアリール基、エポキシシクロヘキシル基、グリシドキシ基、メタクリロキシ基、アクリロキシ基、ウレイド基(-NHCONH2)、チオール基、イソシアネート基(-NCO)、アミノ基、-NHY9基又は-NY10Y11基を表す。
Z8は、ハロゲン原子、アミノ基、ニトロ基、シアノ基又はチオール基を表す。
ジアルコキシシラン化合物の具体例としては、ジメチルジメトキシシラン、ジメチルジエトキシシラン、メチルエチルジメトキシシラン、ジエチルジメトキシシラン、ジエチルジエトキシシラン、メチルプロピルジメトキシシラン、メチルプロピルジエトキシシラン、ジイソプロピルジメトキシシラン、フェニルメチルジメトキシシラン、ビニルメチルジメトキシシラン、3-グリシドキシプロピルメチルジメトキシシシラン、3-グリシドキシプロピルメチルジエトキシシシラン、3-(3,4-エポキシシクロヘキシル)エチルメチルジメトキシシラン、3-メタクリロキシプロピルメチルジメトキシシラン、3-メタクリロキシプロピルメチルジエトキシシラン、3-メルカプトプロピルメチルジメトキシシラン、γ-アミノプロピルメチルジエトキシシラン、N-(2-アミノエチル)アミノプロピルメチルジメトキシシラン、3,3,3-トリフルオロプロピルメチルジメトキシシラン等が挙げられる。
本発明の電荷輸送性ワニスを用いてOLED素子を作製する場合の使用材料や、作製方法としては、下記のようなものが挙げられるが、これらに限定されない。
(1)MALDI-TOF-MS:ブルカー社製、autoflex III smartbeam
(2)1H-NMR:日本電子(株)製、JNM-ECP300 FT NMR SYSTEM
(3)基板洗浄:長州産業(株)製、基板洗浄装置(減圧プラズマ方式)
(4)ワニスの塗布:ミカサ(株)製、スピンコーターMS-A100
(5)膜厚測定:(株)小坂研究所製、微細形状測定機サーフコーダET-4000
(6)EL素子の作製:長州産業(株)製、多機能蒸着装置システムC-E2L1G1-N
(7)EL素子の輝度等の測定:(有)テック・ワールド製、I-V-L測定システム
(8)EL素子の寿命測定(半減期の測定):(株)イーエッチシー製、有機EL輝度寿命評価システムPEL-105S
室温まで放冷後、反応後に析出しているアリールスルホン酸化合物1を再溶解させるために、N,N-ジメチルホルムアミドを更に500mL加え、室温で90分攪拌した。室温攪拌後、この溶液をろ過して炭酸カリウム残渣を除去し、減圧濃縮した。更に、残存している不純物を除去するために、残渣にメタノール100mLを加え、室温で攪拌した。
室温で30分間攪拌後、懸濁溶液をろ過し、ろ物を得た。ろ物に超純水300mLを加えて溶解し、陽イオン交換樹脂ダウエックス650C(ダウ・ケミカル社製、Hタイプ約200mL、留出溶媒:超純水)を用いたカラムクロマトグラフィーによりイオン交換した。
pH1以下の分画を減圧下で濃縮乾固し、残渣を減圧下で乾固して黄色粉末11gを得た(収率85%)。
反応液を室温まで放冷した後、そこへイオン交換水及び酢酸エチルを加えて分液処理をし、得られた有機層を硫酸マグネシウムを用いて乾燥した。
その後、溶媒を減圧留去し、得られた残渣をジオキサン及びイソプロパノールの混合溶媒(1/4(v/v))に溶解させ、この溶液をメタノールへ滴下することで再沈殿を行った。
ろ過によって回収した沈殿物を酢酸エチルで洗浄し、減圧加熱下でよく乾燥して、アニリン誘導体1を得た(収量:12g、収率:73%)。1H-NMRの測定結果を以下に示す。
1H-NMR (300MHz, DMSO-d6) δ[ppm]: 7.94 (s, 2H), 7.21-7.25 (t, 8H), 6.86-7.02 (m, 28H), 3.17 (s, 3H).
攪拌終了後、2mol/L水酸化ナトリウム水溶液30mLを用いて分液処理を行い、得られた有機層をイオン交換水にて2回洗浄した。洗浄後、その有機層を硫酸ナトリウムを用いて乾燥し、乾燥した有機層へ活性炭0.4gを加えて室温で40分攪拌した。その後、活性炭を除去してから有機溶媒を減圧留去した。
得られた残渣から、トルエン4.3gとヘキサン12.9gとを用いて再結晶を行い、ろ過により回収した析出物をよく乾燥して、N,N-ジフェニル-p-フェニレンジアミンを得た(収量:2.41g、収率:74%)。
次いで、得られた有機層を硫酸ナトリウムを用いて乾燥し、その後、減圧下で溶媒を留去し、得られた残渣を80℃に加熱した1,4-ジオキサン(12.5g)に完全に溶解させた。そこへ活性炭0.14gを加えて30分攪拌し、攪拌終了後、活性炭を熱時ろ過により除去し、得られたろ液から有機溶媒を減圧留去した。得られた残渣をトルエン25gに溶解させ、カラムクロマトグラフィーを行い、薄層クロマトグラフィー(TLC)法等により目的物の有無を確認することで目的物を含むフラクションを分取した。
分取したフラクションから減圧下で溶媒を留去した後、得られた残渣を90℃に加熱したトルエン(15.3g)に溶解させて、その溶液を0℃まで冷却し、ろ過により回収した析出物をよく乾燥して、アニリン誘導体2を得た(収量:1.14g、収率:45%)。1H-NMR及びMALDI-TOF-MSの測定結果を以下に示す。
1H-NMR (300MHz, DMSO-d6) δ[ppm]: 8.09 (s, 2H), 7.21-7.26 (m, 11H), 6.91-7.04 (m, 30H).
MALDI-TOF-MS m/Z found: 761.72 ([M]+calcd: 761.35)
次いで、そのろ液と飽和食塩水とを用いて分液処理を行い、得られた有機層を、硫酸ナトリウムを用いて乾燥した後、減圧下で溶媒を留去し、得られた残渣及びクロロホルムを用いてショートカラムを行った。
得られた溶液へ活性炭0.5gを加えて30分攪拌し、その活性炭をろ過により除去した。そのろ液から溶媒を留去することで得た残渣をクロロホルムとn-ヘキサンの混合溶媒(1/1(v/v))に溶解させた。
得られた溶液を用いて、カラムクロマトグラフィーを行い、TLC法等により目的物の有無を確認することで目的物を含むフラクションを分取して、その溶媒を減圧留去した。
得られた残渣を溶解させたトルエン溶液へn-ヘキサンを加えて再沈殿を行い、ろ過によって回収した沈殿物を減圧下でよく乾燥して、アニリン誘導体3を得た(収量:2.01g、収率:39%)。MALDI-TOF-MSの測定結果を以下に示す。
MALDI-TOF-MS m/Z found: 1019.98 ([M]+calcd: 1019.47)
アニリン誘導体1 0.062gとリンタングステン酸(PTA)0.309gとを、窒素雰囲気下で1,3-ジメチル-2-イミダゾリジノン(DMI)4gに溶解させた。得られた溶液に、シクロヘキサノール(CHA)6g及びプロピレングリコール(PG)2gを加えて攪拌し、電荷輸送性ワニスを調製した。
アニリン誘導体1及びPTAの使用量を、それぞれ0.053g及び0.318gとした以外は、実施例2-1と同様の方法で電荷輸送性ワニスを調製した。
アニリン誘導体2 0.062gとPTA0.309gとを、窒素雰囲気下でDMI4gに溶解させた。得られた溶液に、CHA6g及びPG2gを加えて攪拌し、電荷輸送性ワニスを調製した。
アニリン誘導体2及びPTAの使用量を、それぞれ0.053g及び0.318gとした以外は、実施例2-3と同様の方法で電荷輸送性ワニスを調製した。
アニリン誘導体3 0.062gとPTA0.309gとを、窒素雰囲気下でDMI4gに溶解させた。得られた溶液に、CHA6g及びPG2gを加えて攪拌し、電荷輸送性ワニスを調製した。
アニリン誘導体3及びPTAの使用量を、それぞれ0.053g及び0.318gとした以外は、実施例2-5と同様の方法で電荷輸送性ワニスを調製した。
アニリン誘導体1 0.083gとアリールスルホン酸化合物1 0.161gとを、窒素雰囲気下でDMI4gに溶解させた。得られた溶液に、CHA6g及びPG2gを加えて攪拌し、電荷輸送性ワニスを調製した。
アニリン誘導体2 0.088gとアリールスルホン酸化合物1 0.157gとを、窒素雰囲気下でDMI4gに溶解させた。得られた溶液に、CHA6g及びPG2gを加えて攪拌し、電荷輸送性ワニスを調製した。
アニリン誘導体2及びアリールスルホン酸化合物1の使用量を、それぞれ0.073g及び0.172gとした以外は、実施例3-2と同様の方法で電荷輸送性ワニスを調製した。
アニリン誘導体3 0.082gと、アリールスルホン酸化合物1 0.163gを、窒素雰囲気下でDMI4gに溶解させた。得られた溶液に、CHA6g及びPG2gを加えて攪拌し、電荷輸送性ワニスを調製した。
アニリン誘導体3及びアリールスルホン酸化合物1の使用量を、それぞれ0.067g及び0.178gとした以外は、実施例3-4と同様の方法で電荷輸送性ワニスを調製した。
アニリン誘導体1 0.107gとアリールスルホン酸化合物1 0.138gとを、窒素雰囲気下でDMI4gに溶解させた。得られた溶液に、CHA6g及びPG2gを加えて攪拌し、そこへ3,3,3-トリフルオロプロピルトリメトキシシラン0.016g及びフェニルトリメトキシシラン0.008gを加えて更に攪拌し、電荷輸送性ワニスを調製した。
アニリン誘導体1及びアリールスルホン酸化合物1の使用量を、それぞれ0.083g及び0.161gとした以外は、実施例4-1と同様の方法で電荷輸送性ワニスを調製した。
アニリン誘導体2 0.112gとアリールスルホン酸化合物1 0.133gとを、窒素雰囲気下でDMI4gに溶解させた。得られた溶液に、CHA6g及びPG2gを加えて攪拌し、そこへ3,3,3-トリフルオロプロピルトリメトキシシラン0.016g及びフェニルトリメトキシシラン0.008gを加えて更に攪拌し、電荷輸送性ワニスを調製した。
アニリン誘導体2及びアリールスルホン酸化合物1の使用量を、それぞれ0.088g及び0.157g(実施例4-4)、0.073g及び0.172g(実施例4-5)とした以外は、実施例4-3と同様の方法で電荷輸送性ワニスを調製した。
アニリン誘導体3 0.105gとアリールスルホン酸化合物1 0.140gとを、窒素雰囲気下でDMI4gに溶解させた。得られた溶液に、CHA6g及びPG2gを加えて攪拌し、そこへ3,3,3-トリフルオロプロピルトリメトキシシラン0.016g及びフェニルトリメトキシシラン0.008gを加えて更に攪拌し、電荷輸送性ワニスを調製した。
アニリン誘導体3及びアリールスルホン酸化合物1の使用量を、それぞれ0.082g及び0.163g(実施例4-7)、0.067g及び0.178g(実施例4-8)とした以外は、実施例4-6と同様の方法で電荷輸送性ワニスを調製した。
実施例2-1~4-8で得られたワニスをそれぞれスピンコーターを用いてITO基板に塗布した後、50℃で5分間乾燥し、更に、大気雰囲気下、230℃で15分間焼成し、ITO基板上に30nmの均一な薄膜を形成した。ITO基板として、インジウム錫酸化物(ITO)が表面上に膜厚150nmでパターニングされた25mm×25mm×0.7tのガラス基板を用い、使用前にO2プラズマ洗浄装置(150W、30秒間)によって表面上の不純物を除却した。
次いで、薄膜を形成したITO基板に対し、蒸着装置(真空度1.0×10-5Pa)を用いてN,N'-ジ(1-ナフチル)-N,N'-ジフェニルベンジジン(α-NPD)、トリス(8-キノリノラート)アルミニウム(III)(Alq3)、フッ化リチウム、及びアルミニウムの薄膜を順次積層し、有機EL素子を得た。この際、蒸着レートは、α-NPD、Alq3及びアルミニウムについては0.2nm/秒、フッ化リチウムについては0.02nm/秒の条件でそれぞれ行い、膜厚は、それぞれ30nm、40nm、0.5nm及び120nmとした。
なお、空気中の酸素、水等の影響による特性劣化を防止するため、有機EL素子は封止基板により封止した後、その特性を評価した。封止は、以下の手順で行った。
酸素濃度2ppm以下、露点-85℃以下の窒素雰囲気中で、有機EL素子を封止基板の間に収め、封止基板を接着材(ナガセケムテックス(株)製、XNR5516Z-B1)により貼り合わせた。この際、捕水剤(ダイニック(株)製、HD-071010W-40)を有機EL素子と共に封止基板内に収めた。
貼り合わせた封止基板に対し、UV光を照射(波長:365nm、照射量:6,000mJ/cm2)した後、80℃で1時間、アニーリング処理して接着材を硬化させた。
実施例2-1~2-6のワニスを用いて作製した素子の結果を表1に、実施例3-1~3-6のワニスを用いて作製した素子の結果を表2に、実施例4-1~4-8のワニスを用いて作製した素子の結果を表3に示す。
Claims (15)
- 式(1)で表されることを特徴とするアニリン誘導体。
Y1~Y8は、それぞれ独立にZ1で置換されていてもよい炭素数1~20のアルキル基、Z1で置換されていてもよい炭素数2~20のアルケニル基、Z1で置換されていてもよい炭素数2~20のアルキニル基、Z2で置換されていてもよい炭素数6~20のアリール基又はZ2で置換されていてもよい炭素数2~20のヘテロアリール基を表し、
Z1は、ハロゲン原子、ニトロ基、シアノ基、アルデヒド基、水酸基、チオール基、スルホン酸基、カルボン酸基、Z3で置換されていてもよい炭素数6~20のアリール基又はZ3で置換されていてもよい炭素数2~20のヘテロアリール基を表し、
Z2は、ハロゲン原子、ニトロ基、シアノ基、アルデヒド基、水酸基、チオール基、スルホン酸基、カルボン酸基、Z3で置換されていてもよい炭素数1~20のアルキル基、Z3で置換されていてもよい炭素数2~20のアルケニル基又はZ3で置換されていてもよい炭素数2~20のアルキニル基を表し、
Z3は、ハロゲン原子、ニトロ基、シアノ基、アルデヒド基、水酸基、チオール基、スルホン酸基又はカルボン酸基を表す。) - R2~R37が水素原子、ハロゲン原子、Z1で置換されていてもよい炭素数1~20のアルキル基、Z2で置換されていてもよい炭素数6~20のアリール基又は-OY2基である請求項1記載のアニリン誘導体。
- R1が、Z1で置換されていてもよい炭素数1~20のアルキル基、Z2で置換されていてもよい炭素数6~20のアリール基又は式(2)で表される基である請求項1又は2記載のアニリン誘導体。
- R1が式(2)で表される基である請求項3記載のアニリン誘導体。
- R38~R55が水素原子、ハロゲン原子、Z1で置換されていてもよい炭素数1~20のアルキル基、Z2で置換されていてもよい炭素数6~20のアリール基又は-OY2基である請求項4記載のアニリン誘導体。
- 請求項1~5のいずれか1項記載のアニリン誘導体からなる電荷輸送性物質。
- 請求項1~5のいずれか1項記載のアニリン誘導体、ドーパント及び有機溶媒を含む電荷輸送性ワニス。
- 請求項7記載の電荷輸送性ワニスを用いて作製される電荷輸送性薄膜。
- 請求項1~5のいずれか1項記載のアニリン誘導体を含む電荷輸送性薄膜。
- 請求項8又は9記載の電荷輸送性薄膜を少なくとも1層備える電子デバイス。
- 請求項8又は9記載の電荷輸送性薄膜を少なくとも1層備える有機エレクトロルミネッセンス素子。
- 前記電荷輸送性薄膜が、正孔注入層又は正孔輸送層である請求項11記載の有機エレクトロルミネッセンス素子。
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KR1020167001186A KR102257209B1 (ko) | 2013-06-21 | 2014-06-17 | 아닐린 유도체, 전하 수송성 바니시 및 유기 일렉트로루미네선스 소자 |
US14/899,854 US10164196B2 (en) | 2013-06-21 | 2014-06-17 | Aniline derivative, charge-transporting varnish and organic electroluminescent device |
CN201480035252.6A CN105324360B (zh) | 2013-06-21 | 2014-06-17 | 苯胺衍生物、电荷传输性清漆以及有机电致发光元件 |
JP2015522925A JP6061034B2 (ja) | 2013-06-21 | 2014-06-17 | アニリン誘導体、電荷輸送性ワニス及び有機エレクトロルミネッセンス素子 |
EP14813882.9A EP3012245B1 (en) | 2013-06-21 | 2014-06-17 | Aniline derivative, charge-transporting varnish and organic electroluminescent device |
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EP (1) | EP3012245B1 (ja) |
JP (1) | JP6061034B2 (ja) |
KR (1) | KR102257209B1 (ja) |
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CN107895760A (zh) * | 2017-12-01 | 2018-04-10 | 苏州宝澜环保科技有限公司 | 一种硅纳米线阵列异质结太阳能电池及其制备方法 |
WO2020027014A1 (ja) * | 2018-08-01 | 2020-02-06 | 日産化学株式会社 | 重合体及びその利用 |
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CN113631536A (zh) * | 2019-03-29 | 2021-11-09 | 日产化学株式会社 | 芴衍生物及其利用 |
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- 2014-06-17 EP EP14813882.9A patent/EP3012245B1/en not_active Expired - Fee Related
- 2014-06-17 WO PCT/JP2014/065999 patent/WO2014203882A1/ja active Application Filing
- 2014-06-17 CN CN201480035252.6A patent/CN105324360B/zh active Active
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WO2020027014A1 (ja) * | 2018-08-01 | 2020-02-06 | 日産化学株式会社 | 重合体及びその利用 |
JPWO2020027014A1 (ja) * | 2018-08-01 | 2021-08-10 | 日産化学株式会社 | 重合体及びその利用 |
JP7322884B2 (ja) | 2018-08-01 | 2023-08-08 | 日産化学株式会社 | 重合体及びその利用 |
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Publication number | Publication date |
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EP3012245A1 (en) | 2016-04-27 |
JPWO2014203882A1 (ja) | 2017-02-23 |
KR102257209B1 (ko) | 2021-05-27 |
CN105324360B (zh) | 2018-06-22 |
US10164196B2 (en) | 2018-12-25 |
KR20160021447A (ko) | 2016-02-25 |
EP3012245B1 (en) | 2018-08-08 |
US20160141507A1 (en) | 2016-05-19 |
EP3012245A4 (en) | 2017-01-25 |
JP6061034B2 (ja) | 2017-01-18 |
CN105324360A (zh) | 2016-02-10 |
TW201512154A (zh) | 2015-04-01 |
TWI603946B (zh) | 2017-11-01 |
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