WO2015178407A1 - 電荷輸送性ワニス - Google Patents
電荷輸送性ワニス Download PDFInfo
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- WO2015178407A1 WO2015178407A1 PCT/JP2015/064418 JP2015064418W WO2015178407A1 WO 2015178407 A1 WO2015178407 A1 WO 2015178407A1 JP 2015064418 W JP2015064418 W JP 2015064418W WO 2015178407 A1 WO2015178407 A1 WO 2015178407A1
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- carbon atoms
- substituted
- charge transporting
- thin film
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- 239000002966 varnish Substances 0.000 title claims abstract description 69
- -1 organosilane compound Chemical class 0.000 claims abstract description 211
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 134
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 74
- 239000010409 thin film Substances 0.000 claims abstract description 63
- 125000005843 halogen group Chemical group 0.000 claims abstract description 55
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
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- 238000009833 condensation Methods 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 47
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 238000005401 electroluminescence Methods 0.000 claims description 29
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- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 230000005525 hole transport Effects 0.000 claims description 16
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- 238000002347 injection Methods 0.000 claims description 15
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- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
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- 125000001153 fluoro group Chemical group F* 0.000 description 16
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- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 6
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- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
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- 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
- 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 3
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- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
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- 229910052771 Terbium Inorganic materials 0.000 description 1
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- WIHKEPSYODOQJR-UHFFFAOYSA-N [9-(4-tert-butylphenyl)-6-triphenylsilylcarbazol-3-yl]-triphenylsilane Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C2=CC=C([Si](C=3C=CC=CC=3)(C=3C=CC=CC=3)C=3C=CC=CC=3)C=C2C2=CC([Si](C=3C=CC=CC=3)(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=C21 WIHKEPSYODOQJR-UHFFFAOYSA-N 0.000 description 1
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- 230000009471 action Effects 0.000 description 1
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
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- 125000002078 anthracen-1-yl 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 1
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- FCDNEESKPPIAJZ-UHFFFAOYSA-N bis[3,5-di(carbazol-9-yl)phenyl]-diphenylsilane Chemical compound C1=CC=CC=C1[Si](C=1C=C(C=C(C=1)N1C2=CC=CC=C2C2=CC=CC=C21)N1C2=CC=CC=C2C2=CC=CC=C21)(C=1C=C(C=C(C=1)N1C2=CC=CC=C2C2=CC=CC=C21)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 FCDNEESKPPIAJZ-UHFFFAOYSA-N 0.000 description 1
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- CJMZLCRLBNZJQR-UHFFFAOYSA-N ethyl 2-amino-4-(4-fluorophenyl)thiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC=C1C1=CC=C(F)C=C1 CJMZLCRLBNZJQR-UHFFFAOYSA-N 0.000 description 1
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- 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 1
- 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 1
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- UWCPBTNCCSZKGT-UHFFFAOYSA-N platinum 25,26,27,28-tetrazahexacyclo[16.6.1.13,6.18,11.113,16.019,24]octacosa-1(25),2,4,6,8(27),9,11,13,15,17,19,21,23-tridecaene Chemical compound [Pt].N1C(C=C2C3=CC=CC=C3C(C=C3NC(=C4)C=C3)=N2)=CC=C1C=C1C=CC4=N1 UWCPBTNCCSZKGT-UHFFFAOYSA-N 0.000 description 1
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- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-N potassium;ethoxymethanedithioic acid Chemical group [K+].CCOC(S)=S JCBJVAJGLKENNC-UHFFFAOYSA-N 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical group C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 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
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- CGFYHILWFSGVJS-UHFFFAOYSA-N silicic acid;trioxotungsten Chemical compound O[Si](O)(O)O.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 CGFYHILWFSGVJS-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
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- 230000001629 suppression Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
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- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer 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
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- FCIABWJRBPKYJO-UHFFFAOYSA-N triethoxy(furan-3-yl)silane Chemical compound CCO[Si](OCC)(OCC)C=1C=COC=1 FCIABWJRBPKYJO-UHFFFAOYSA-N 0.000 description 1
- SAWDTKLQESXBDN-UHFFFAOYSA-N triethoxy(heptyl)silane Chemical compound CCCCCCC[Si](OCC)(OCC)OCC SAWDTKLQESXBDN-UHFFFAOYSA-N 0.000 description 1
- 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
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 description 1
- FHVAUDREWWXPRW-UHFFFAOYSA-N triethoxy(pentyl)silane Chemical compound CCCCC[Si](OCC)(OCC)OCC FHVAUDREWWXPRW-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-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
- PBTDWUVVCOLMFE-UHFFFAOYSA-N triethoxy-[4-(trifluoromethyl)phenyl]silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=C(C(F)(F)F)C=C1 PBTDWUVVCOLMFE-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- HILHCDFHSDUYNX-UHFFFAOYSA-N trimethoxy(pentyl)silane Chemical compound CCCCC[Si](OC)(OC)OC HILHCDFHSDUYNX-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- XFFHTZIRHGKTBQ-UHFFFAOYSA-N trimethoxy-(2,3,4,5,6-pentafluorophenyl)silane Chemical compound CO[Si](OC)(OC)C1=C(F)C(F)=C(F)C(F)=C1F XFFHTZIRHGKTBQ-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 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
- 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-UHFFFAOYSA-L 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
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- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D165/00—Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Coating compositions based on derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/02—Polyamines
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/24—Electrically-conducting paints
-
- H—ELECTRICITY
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Definitions
- the present invention relates to a charge transporting varnish, and more specifically, to a charge transporting varnish containing an organic silane compound obtained by hydrolytic condensation of a predetermined alkoxysilane compound.
- organic electroluminescence (EL) elements are expected to be put into practical use in the fields of displays and lighting, in recent years, various developments regarding materials and element structures have been aimed at low voltage drive, high brightness, long life, etc. Has been made.
- this organic EL element a plurality of functional thin films are used from the viewpoint of enhancing the performance.
- the hole injection layer and the hole transport layer are responsible for charge transfer between the anode and the light emitting layer, and the voltage of the organic EL element. It performs important functions to achieve drive reduction and brightness enhancement.
- the formation method of the hole injection layer and the hole transport layer is roughly divided into a dry process represented by a vapor deposition method and a wet process represented by a spin coating method. Since a thin film having a large area and high flatness can be manufactured more efficiently, a wet process is often used particularly in the display field.
- the present invention has been made in view of the above circumstances, and has charge transportability capable of providing a thin film that has high flatness and high charge transportability and can realize excellent luminance characteristics when applied to an organic EL element.
- the purpose is to provide a varnish.
- a charge transport varnish containing a charge transporting substance and an organic solvent and further containing a predetermined organosilane compound has high flatness and high flatness.
- the inventors have found that a charge-transporting thin film can be provided, and found that when the thin film is applied to an organic EL element, excellent luminance characteristics can be realized, and the present invention has been completed.
- prescribed siloxane type substance in the composition containing conductive polymers, such as a polystyrene sulfonic acid and polyaniline Although it has been reported that characteristics and lifetime can be improved (see Patent Documents 1 and 2), there is no report on a charge transporting varnish containing an organosilane compound used in the present invention.
- the present invention 1.
- R 1 each independently represent an alkyl group or an aryl group which carbon number of 6 to 20 substituted with Z 2, of which carbon number of 1 to 20 substituted by Z 1, R 2 are each Independently, it represents an alkyl group having 1 to 20 carbon atoms which may be substituted with Z 3 , wherein Z 1 represents a halogen atom, a cyano group, a nitro group or an alkoxy group having 1 to 20 carbon atoms substituted with Z 3 represents a heteroaryl group
- the alkoxysilane compound is represented by the formulas (2-1) to (2-3) and at least one selected from the alkoxysilane compounds represented by the formulas (1-1) and (1-2).
- 1 charge transporting varnish containing at least one selected from the following alkoxysilane compounds: Si (OR 3 ) 4 (2-1) SiR 4 2 (OR 3 ) 2 (2-2) SiR 4 (OR 3 ) 3 (2-3)
- each R 3 independently represents an alkyl group having 1 to 20 carbon atoms which may be substituted with Z 3
- each R 4 independently represents an alkyl group having 1 to 20 carbon atoms
- Z 4-substituted-2 carbon atoms which may be 20 alkenyl group is substituted with Z 4 with carbon atoms which may be substituted have 2-20 alkynyl group, an aryl group having 6 to 20 carbon atoms, or Z 5
- Z 3 represents the same meaning as described above, and
- 1 or 2 charge transporting varnishes wherein the alkoxysilane compound comprises an alkoxylane compound represented by the formula (1-1) and an alkoxysilane compound represented by the formula (2-1); 4).
- a method for producing a charge-transporting thin film comprising applying the charge-transporting varnish of any one of 1 to 4 onto a substrate and evaporating the solvent; 9.
- a method for producing an organic electroluminescence device comprising using the charge transporting thin film of 5; 10.
- a method for deepening the ionization potential of a charge-transporting thin film obtained from a charge-transporting varnish containing a charge-transporting substance and an organic solvent comprising the formulas (1-1) and (1-2) Ionization of a charge transporting thin film characterized by adding a polymer having a weight average molecular weight of 500 to 10,000 prepared by hydrolytic condensation of an alkoxysilane compound containing at least one selected from the alkoxysilane compounds represented by Potential deepening method, SiR 1 (OR 2 ) 3 (1-1) SiR 1 2 (OR 2 ) 2 (1-2) (Wherein, R 1 each independently represent an alkyl group or an aryl group which carbon number of 6 to 20 substituted with Z 2, of which carbon number of 1 to 20 substituted by Z 1, R 2 are each Independently, it represents an alkyl group having 1 to 20 carbon atoms which may be substituted with Z 3 , wherein Z 1 represents a halogen atom, a cyano group, a nitro group or an al
- a method for deepening an ionization potential of a charge transporting thin film containing a charge transporting substance wherein the alkoxy compound represented by formulas (1-1) and (1-2) is used together with the charge transporting substance at the time of preparing the charge transporting thin film.
- a polymer having a weight average molecular weight of 500 to 10,000 prepared by hydrolytic condensation of an alkoxysilane compound containing at least one selected from silane compounds is used, and the polymer is introduced into the charge transporting thin film.
- R 1 each independently represent an alkyl group or an aryl group which carbon number of 6 to 20 substituted with Z 2, of which carbon number of 1 to 20 substituted by Z 1, R 2 are each Independently, it represents an alkyl group having 1 to 20 carbon atoms which may be substituted with Z 3 , wherein Z 1 represents a halogen atom, a cyano group, a nitro group or an alkoxy group having 1 to 20 carbon atoms substituted with Z 3 represents a heteroaryl group which Z 3 substituted aryl group having 6 to 20 carbon atoms or Z 3 is a C 2-20 substituted with,, Z 2 is a halogen atom, a cyano group, a nitro group, or Z, 3 represents an alkyl group having 1 to 20 carbon atoms substituted with 3 , and Z 3 represents a
- the charge transporting varnish of the present invention By using the charge transporting varnish of the present invention, a charge transporting thin film with good flatness can be obtained with good reproducibility by various wet processes. Further, since the charge transporting varnish of the present invention contains a predetermined organosilane compound, the ionization potential of the obtained thin film becomes deeper than when a varnish not containing this is used. The barrier for charge transport between the functional thin film on the cathode side in contact with the cathode can be reduced.
- the charge transporting thin film of the present invention having good flatness and a suitable ionization potential to a hole injection layer or a hole transport layer of an organic EL device, preferably a hole transport layer, The luminance characteristics can be improved.
- 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.
- the charge transporting thin film of the present invention is also expected to be applied to capacitor electrode protective films, antistatic films, anode buffer layers of organic thin film solar cells, and the like.
- the charge transporting varnish according to the present invention includes a charge transporting material, an organic silane compound comprising a polymer having a weight average molecular weight of 500 to 10,000 prepared by hydrolytic condensation of an alkoxysilane compound in advance, and an organic solvent.
- the alkoxysilane compound contains at least one selected from the alkoxysilane compounds represented by the formulas (1-1) and (1-2). In consideration of further increasing the molecular weight of the polymer, Those containing a trialkoxysilane compound represented by (1-1) are preferred. SiR 1 (OR 2 ) 3 (1-1) SiR 1 2 (OR 2 ) 2 (1-2)
- each R 1 independently represents an alkyl group having 1 to 20 carbon atoms substituted with Z 1 or an aryl group having 6 to 20 carbon atoms substituted with Z 2
- R 2 represents each independently Represents an alkyl group having 1 to 20 carbon atoms which may be substituted with Z 3 , wherein Z 1 is a halogen atom, a cyano group, a nitro group, an alkoxy group having 1 to 20 carbon atoms substituted with Z 3 ; represents a heteroaryl group which Z 3 substituted aryl group having 6 to 20 carbon atoms or Z 3 is a C 2-20 substituted with,, Z 2 is a halogen atom, a cyano group, a nitro group, or Z 3, Represents an alkyl group having 1 to 20 carbon atoms and substituted with Z 3 represents a halogen atom, a cyano group, or a nitro group.
- halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- the alkyl group having 1 to 20 carbon atoms may be linear, branched, or cyclic.
- alkoxy group having 1 to 20 carbon atoms include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butyloxy group, isobutyloxy group, s-butyloxy group, t-butyloxy group, n- A linear or branched alkyl group having 1 to 20 carbon atoms such as pentyloxy group, n-hexyloxy group, n-heptyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group, etc .; cyclopropyl Examples thereof include cyclic alkyl groups having 3 to 20 carbon atoms such as oxy group, cyclobutyloxy group, cyclopentyloxy group, cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group, cyclononyloxy group, and cyclodec
- 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 alkyl 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.
- Z 1 and Z 2 a halogen atom is preferable, and a fluorine atom is optimal, and Z 3 is preferably absent (that is, unsubstituted) in R 2 , and in Z 1 and Z 2 , Halogen atoms are preferred, and fluorine atoms are optimal.
- the alkyl group of Z 3 carbon number of 1 to 20 substituted with the alkyl group having 1 to 20 carbon atoms, at least one hydrogen atom include those substituted with Z 3, as specific examples thereof, Chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trichloroethyl, pentachloroethyl Group, 2,2,2-tribromoethyl group, pentabromoethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group, 3,3,3-trichloropropyl group, 2,2,3, 3-tetrachloropropyl group, 2,2,3,3,3-pentachloropropyl group, heptachloropropyl group, heptachloroisopropyl Group, 3,3,3-tribromopropyl group, 2,2,
- the alkyl group of Z 1 carbon number of 1 to 20 substituted with the alkyl group having 1 to 20 carbon atoms, at least one hydrogen atom include those substituted with Z 1, as specific examples thereof, In addition to the groups exemplified for the alkyl group having 1 to 20 carbon atoms substituted with Z 3 , 3- (heptafluoroisopropoxy) propyl group, 4-trifluoromethylphenylmethyl group and the like can be mentioned.
- An alkyl group substituted with an alkoxy group having a halogen atom, an aryl group or a heteroaryl group is preferred, and an alkyl group substituted with an alkoxy group having a fluorine atom, an aryl group or a heteroaryl group is more preferred.
- alkoxy groups of Z 3 carbon number of 1 to 20 substituted by may exclude hydrogen atoms on hydroxyl groups from an alcohol having an alkyl group of carbon number of 1 to 20 substituted by Z 3 described above Groups such as chloromethoxy group, dichloromethoxy group, trichloromethoxy group, bromomethoxy group, dibromomethoxy group, tribromomethoxy group, fluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2,2,2 -Trichloroethoxy group, pentachloroethoxy group, 2,2,2-tribromoethoxy group, pentabromoethoxy group, 2,2,2-trifluoroethoxy group, pentafluoroethoxy group, 3,3,3-trichloropropoxy Group, 2,2,3,3-tetrachloropropoxy group, 2,2,3,3,3-pentachloropro Poxy group, heptachloropropoxy group, heptachloroiso
- Examples of the aryl group Z 3 carbon number of 6 to 20 substituted with, in the aryl group for 6 to 20 carbon atoms, at least one hydrogen atom include those substituted with Z 3, as specific examples thereof, 4-chlorophenyl group, 4-bromophenyl group, 4-fluorophenyl group, 2,4-dichlorophenyl group, 2,4-dibromophenyl group, 2,4-difluorophenyl group, pentachlorophenyl group, pentabromophenyl group, penta Halogenated aryl groups such as fluorophenyl group; Cyanoaryl groups such as 4-cyanophenyl, 2,4-dicyanophenyl group, 2,4,6-tricyanophenyl group; 4-nitrophenyl group, 2,4-dinitro Examples thereof include a nitroaryl group such as a phenyl group and 2,4,6-trinitrophenyl group, but a halogenated aryl group is preferred.
- a fluorinated aryl group More preferred is a fluorinated aryl group.
- the aryl group having 6 to 20 carbon atoms substituted with Z 2 include 4-trichloromethylphenyl group, 4-tribromo, in addition to the groups exemplified as the aryl group having 6 to 20 carbon atoms substituted with Z 3.
- An aryl group having a halogenated alkyl group such as a methylphenyl group and a 4-trifluoromethylphenyl group is exemplified, and an aryl group having a fluorinated alkyl group is preferred.
- the heteroaryl groups of Z 3 carbon number of 2-20 substituted with at heteroaryl groups of 2 to 20 carbon atoms include those with at least one hydrogen atom substituted with Z 3, and specific examples thereof Are 5-chloro-thiophen-2-yl group, 5-bromo-thiophen-2-yl group, 5-fluoro-thiophen-2-yl group, 5-chloro-thiophen-3-yl group, 5-bromo- Halogenated thienyl groups such as thiophen-3-yl group and 5-fluoro-thiophen-3-yl group; cyanothienyl groups such as 5-cyano-thiophen-2-yl group and 5-cyano-thiophen-3-yl group Nitrothienyl groups such as 5-nitro-thiophen-2-yl group and 5-nitro-thiophen-3-yl group; 5-chloro-furan-2-yl group, 5-bromo-furan-2-yl Group, 5-fluoro-furan-2-yl group, 5-chloro
- cyanofuranyl groups such as 5-cyano-furan-2-yl group and 5-cyano-furan-3-yl group; 5-nitro-furan-2-yl group, 5-nitro-furan-3-yl group and the like
- trialkoxysilane represented by the above formula (1-1) include triethoxy (4- (trifluoromethyl) phenyl) silane, 3,3,3-trifluoropropyltrimethoxysilane, perfluorooctyltrisilane.
- dialkoxysilane represented by the above formula (1-2) include 3,3,3-trifluoropropylmethyldimethoxysilane and the like.
- the formulas (2-1) to (2) -3) may be used in combination with at least one selected from the alkoxysilane compounds represented by formula (2-1).
- the tetrasilane represented by formula (2-1) It is preferable to use an alkoxysilane compound in combination.
- each R 3 independently represents an alkyl group having 1 to 20 carbon atoms which may be substituted with Z 3
- each R 4 independently represents an alkyl group having 1 to 20 carbon atoms
- Z 4 An alkenyl group having 2 to 20 carbon atoms which may be substituted with, an alkynyl group having 2 to 20 carbon atoms which may be substituted with Z 4 , an aryl group having 6 to 20 carbon atoms, or a substituent with Z 5
- Z 4 represents a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, or an aryl group having 6 to 20 carbon atoms which may be substituted with Z 6.
- An alkenyl group or an alkynyl group which 1 carbon atoms which may be ⁇ 20 substituted with Z 6, of Z 6 is - 1 carbon atoms and optionally 20 substituted with,
- Z 6 represents a halogen atom, a nitro group
- Z 3 represents the same meaning as described above.
- alkenyl group having 2 to 20 carbon atoms include ethenyl group, n-1-propenyl group, n-2-propenyl group, 1-methylethenyl group, n-1-butenyl group, n-2-butenyl group, n-3-butenyl group, 2-methyl-1-propenyl group, 2-methyl-2-propenyl group, 1-ethylethenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, n- Examples thereof include a 1-pentenyl group, an n-1-decenyl group, and an n-1-eicosenyl group.
- alkynyl group having 2 to 20 carbon atoms examples include ethynyl group, n-1-propynyl group, n-2-propynyl group, n-1-butynyl group, n-2-butynyl group, and n-3-butynyl.
- 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 3 is preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and further preferably a methyl group or an ethyl group.
- R 4 is preferably an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 14 carbon atoms, An alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 10 carbon atoms is still more preferable, and an alkyl group having 1 to 4 carbon atoms or a phenyl group is more preferable.
- a plurality of R 3 may be all the same or different, and a plurality of R 4 may all be the same or different.
- Z 3 is preferably a halogen atom, more preferably a fluorine atom, and most preferably not present (that is, unsubstituted).
- a halogen atom a phenyl group which may be substituted with Z 6, good furanyl preferably substituted with Z 6, and more preferably a halogen atom, a fluorine atom or the absence, ( That is, it is even more preferable that it is unsubstituted.
- a halogen atom a furanyl group is preferable optionally substituted with an alkyl group, Z 6 of which do ⁇ 1 to 20 carbon atoms substituted with Z 6, more preferably a halogen atom, a fluorine atom Or even absent (ie, unsubstituted) is even more preferred.
- Z 6 is preferably a halogen atom, more preferably a fluorine atom or not (that is, unsubstituted).
- tetraalkoxysilane compound represented by the above formula (2-1) examples include tetraethoxysilane, tetramethoxysilane, and tetrapropoxysilane.
- dialkoxysilane compound represented by the above formula (2-2) include dimethyldimethoxysilane, dimethyldiethoxysilane, methylethyldimethoxysilane, diethyldimethoxysilane, diethyldiethoxysilane, methylpropyldimethoxysilane, methyl Examples include propyldiethoxysilane, diisopropyldimethoxysilane, phenylmethyldimethoxysilane, and vinylmethyldimethoxysilane.
- trialkoxysilane compounds represented by the above formula (2-3) include methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, propyltrimethoxysilane, and propyltriethoxysilane.
- the content of the organosilane compound is usually about 0.1 to 50% by mass with respect to the mass of the charge transporting substance. In consideration of suppression, 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 organic silane compound (polymer) can be obtained, for example, by hydrolyzing and condensing a single substance or a mixture of two or more of the above-mentioned alkoxysilane compounds in the presence of water.
- the method for hydrolysis is not particularly limited, and a general method may be used.
- an acid or a base can be used as a catalyst.
- the charge transporting material used in the present invention is not limited as long as it is a charge transporting monomer, charge transporting oligomer or polymer conventionally used in organic EL devices.
- aniline derivatives for example, aniline derivatives, thiophene derivatives, pyrrole derivatives, etc.
- Various hole transporting substances can be mentioned, among which aniline derivatives and thiophene derivatives are preferable, and aniline derivatives are more preferable.
- aniline derivatives include those represented by the following formula (3).
- X 1 represents —NY 1 —, —O—, —S—, — (CR 11 R 12 ) L —, or a single bond, and when m or n is 0, —NY 1 — is represented.
- Y 1 is independently of each other a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms or an alkynyl group having 2 to 20 carbon atoms, which may be substituted with Z 7 , or An aryl group having 6 to 20 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms, which may be substituted with Z 8 , is represented.
- Specific examples of the alkyl group, alkenyl group, alkynyl group, aryl group, and heteroaryl group include those described above.
- R 11 and R 12 are each independently substituted with a hydrogen atom, a halogen atom, a nitro group, a cyano group, an amino group, an aldehyde group, a hydroxyl group, a thiol group, a sulfonic acid group, a carboxylic acid group, or Z 7.
- Y 2 to Y 13 each independently represent an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, or an alkynyl group having 2 to 20 carbon atoms, which may be substituted with Z 7 , or An aryl group having 6 to 20 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms, which may be substituted with Z 8 , is represented.
- Z 7 is a halogen atom, a nitro group, a cyano group, an amino group, an aldehyde group, a hydroxyl group, a thiol group, a sulfonic acid group, a carboxylic acid group, or an aryl having 6 to 20 carbon atoms which may be substituted with Z 9 Or a heteroaryl group having 2 to 20 carbon atoms.
- Z 8 is a halogen atom, a nitro group, a cyano group, an amino group, an aldehyde group, a hydroxyl group, a thiol group, a sulfonic acid group, a carboxylic acid group, or an alkyl having 1 to 20 carbon atoms which may be substituted with Z 9 A alkenyl group having 2 to 20 carbon atoms or an alkynyl group having 2 to 20 carbon atoms.
- Z 9 is a halogen atom, nitro group, cyano group, amino group, aldehyde group, hydroxyl group, thiol group, sulfonic acid group, or carboxylic acid group.
- halogen atom alkyl group, alkenyl group, alkynyl group, aryl group and heteroaryl group of R 11 to R 12 and Y 2 to Y 13 are the same as those described above.
- R 11 and R 12 hydrogen atom or an alkyl group of Z 7 is 1 carbon atoms which may be ⁇ 20 substituted by are preferred, and a methyl group which may be substituted with a hydrogen atom or Z 7 More preferred are both hydrogen atoms.
- L represents the number of repeating units of a divalent alkylene group represented by — (CR 11 R 12 ) — and is an integer of 1 to 20, preferably 1 to 10, more preferably 1 to 5, ⁇ 2 is even more preferred, with 1 being optimal.
- the plurality of R 11 may be the same as or different from each other, and the plurality of R 12 may be the same as or different from each other.
- X 1 is preferably —NY 1 — or a single bond.
- Y 1 hydrogen atom or an alkyl group of Z 7 which do ⁇ 1 to 20 carbon atoms substituted with, more preferably a methyl group which may be substituted with a hydrogen atom or Z 7, hydrogen atom Is the best.
- R 5 to R 8 are each independently substituted with a hydrogen atom, a halogen atom, a nitro group, a cyano group, an amino group, an aldehyde group, a hydroxyl group, a thiol group, a sulfonic acid group, a carboxylic acid group, or Z 7.
- R 5 to R 8 may be substituted with a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms which may be substituted with Z 7 , or Z 8.
- An aryl group having 6 to 14 carbon atoms is preferable, a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 10 carbon atoms which may be substituted with a fluorine atom is more preferable, and all hydrogen atoms are optimal.
- R 9 and R 10 are each a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms that may be substituted with Z 7 , or an aryl group having 6 to 14 carbon atoms that may be substituted with Z 8.
- a diphenylamino group optionally substituted with Z 8 (Y 3 and Y 4 are a phenyl group optionally substituted with Z 8 —NY 3 Y 4 group), preferably a hydrogen atom, a fluorine atom Or a diphenylamino group optionally substituted with a fluorine atom, more preferably a hydrogen atom or a diphenylamino group.
- R 5 to R 8 are hydrogen atoms, fluorine atoms, alkyl groups having 1 to 10 carbon atoms which may be substituted with fluorine atoms
- R 9 and R 10 are hydrogen atoms, fluorine atoms, fluorine atoms A diphenylamino group which may be substituted with, X 1 is —NY 1 — or a single bond
- Y 1 is preferably a hydrogen atom or a combination of methyl groups
- R 5 to R 8 are hydrogen atoms
- R 9 and R 9 More preferably, 10 is a hydrogen atom or a diphenylamino group, and X 1 is —NH— or a combination of single bonds.
- m and n each independently represent an integer of 0 or more and satisfy 1 ⁇ m + n ⁇ 20, but considering the balance between the charge transportability of the resulting thin film and the solubility of the aniline derivative. Then, it is preferable to satisfy 2 ⁇ m + n ⁇ 8, more preferably 2 ⁇ m + n ⁇ 6, and still more preferably satisfy 2 ⁇ m + n ⁇ 4.
- the substituent Z 7 is preferably a halogen atom or an aryl group having 6 to 20 carbon atoms which may be substituted with Z 9.
- the phenyl group which may be substituted with 9 is more preferred and is optimally absent (ie, unsubstituted).
- the substituent Z 8 is halogen atom or preferably an alkyl group which may having 1 to 20 carbon atoms optionally substituted by Z 9, halogen atom or Z carbon atoms 1 optionally substituted 9 to 4, It is more preferable that the alkyl group is not present (that is, unsubstituted).
- the substituent Z 9 is preferably a halogen atom, more preferably fluorine, and optimally not present (that is, unsubstituted).
- 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.
- the molecular weight of the aniline derivative is usually 300 to 5,000, but is preferably 4,000 or less, more preferably 3,000 or less, and even more preferably 2,000, from the viewpoint of enhancing solubility. It is as follows.
- the method for synthesizing the aniline derivative is not particularly limited, but Bulletin of Chemical Society of Japan, 67, pp.1749-1752, (1994), Synthetic Metals, 84, pp.119-120, (1997), Thin Solid Films, 520 (24), pp. 7157-7163, (2012), International Publication No. 2008/032617, International Publication No. 2008/032616, International Publication No. 2008/129947, International Publication No. The method as described in 2013/084664 etc. is mentioned.
- aniline derivative represented by the formula (3) examples include phenyldianiline, phenyltrianiline, phenyltetraaniline, phenylpentaaniline, tetraaniline (aniline tetramer), octaaniline (aniline octamer), Although hexadecaaniline (aniline 16-mer) and what is represented by a following formula are mentioned, it is not limited to these.
- Ph represents a phenyl group
- DPA represents a diphenylamino group
- TPA represents a 4- (diphenylamino) phenyl group.
- the charge transporting substance various compounds conventionally used widely as hole transporting materials may be used.
- the hole transporting low molecular weight material include (triphenylamine) dimer derivative, [(triphenylamine) dimer] spirodimer, 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 (naphthalene) -1-yl) -N, N′-bis (phenyl) -9,9-spirobifluorene,
- aniline derivatives disclosed in International Publication No. 2015/050253 can be suitably used.
- the content of the charge transporting substance in the varnish of the present invention is preferably about 0.1 to 20% by mass relative to the whole varnish.
- the charge transporting varnish of the present invention may contain a dopant substance for the purpose of improving its charge transporting ability, etc., depending on the use of the resulting thin film.
- the dopant substance is not particularly limited as long as it dissolves in at least one solvent used for the varnish, and any of inorganic dopant substances and organic dopant substances can be used.
- Inorganic dopant materials include heteropolyacids such as phosphomolybdic acid, silicomolybdic acid, phosphotungstic acid, phosphotungstomolybdic acid and silicotungstic acid; strong 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 ) Metal halides such as copper chloride (II) (CuCl 2 ), antimony pentachloride (V) (SbCl 5 ), arsenic pentafluoride (V) (AsF 5 ), phosphorus pentafluoride (PF 5 ), Cl 2 , Halogens such as Br 2 , I 2 , IC
- organic dopant substances include 7,7,8,8-tetracyanoquinodimethane (TCNQ), 2-fluoro-7,7,8,8-tetracyanoquinodimethane, and 2,5-difluoro.
- Tetracyanoquinodimethanes such as -7,7,8,8-tetracyanoquinodimethane; tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), tetrachloro-7,7, 8,8-tetracyanoquinodimethane, 2-fluoro-7,7,8,8-tetracyanoquinodimethane, 2-chloro-7,7,8,8-tetracyanoquinodimethane, 2,5- Halotetracyanoquinodimethanes (haloTCNQ) such as difluoro-7,7,8,8-tetracyanoquinodimethane, 2,5-dichloro-7,7,8,8-te
- arylsulfonic acid derivative described in International Publication No. 2006/025342, JP-A-2005-108828 Aryl sulfonic acid compounds such as dinonylnaphthalene sulfonic acid derivatives described in the publication, aromatic sulfonic compounds such as polystyrene sulfonic acid; non-aromatic sulfonic compounds such as 10-camphor sulfonic acid, and the like.
- aromatic sulfonic compounds such as polystyrene sulfonic acid
- non-aromatic sulfonic compounds such as 10-camphor sulfonic acid, and the like.
- These inorganic and organic dopant materials may be used alone or in combination of two or more.
- the organic solvent used in preparing the charge transporting varnish is not particularly limited as long as it has the ability to dissolve each component used in the varnish.
- benzene, toluene, xylene, ethylbenzene, chlorobenzene Aromatic hydrocarbon solvents such as n-heptane, n-hexane, cyclohexane; ether solvents such as diethyl ether, tetrahydrofuran, dioxane, 1,2-dimethoxyethane; acetone Ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; ester solvents such as ethyl acetate, normal hexyl acetate, ethyl lactate and ⁇ -butyrolactone; halogenated carbons such as methylene chloride, dichloromethane, 1,2-dichloroethane and chloroform Hydrogen solvents: Am
- 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. In consideration of improving the coatability of the varnish, it is preferably about 0.5 to 5.0% by mass, more preferably about 1.0 to 3.0% by mass.
- solid content here means the charge transport substance and dopant substance which are contained in the charge transport varnish of this invention.
- a charge transporting thin film can be formed on a base material by applying the charge transporting varnish described above 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 intended use of the obtained thin film, the degree of charge transportability imparted to the obtained thin film, the type and boiling point of the solvent, and the like.
- the obtained thin film is used as a hole injection layer of an organic EL device, it is preferably about 140 to 250 ° C., more preferably about 145 to 240 ° C.
- a temperature change of two or more steps may be applied for the purpose of developing a higher uniform film forming property or causing the reaction to proceed on the substrate. What is necessary is just to perform using suitable apparatuses, such as oven.
- the film 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 or a hole transport 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.
- the charge transporting varnish of the present invention contains a predetermined organic silane compound, and as a result, the thin film obtained using the varnish also contains the predetermined organic silane compound.
- This increases the ionization potential of the thin film. That is, it can be said that the predetermined silane compound has an action of deepening the ionization potential of the charge transporting thin film containing the charge transporting substance. Therefore, by applying the charge transporting thin film of the present invention to a hole injection layer or a hole transporting layer of an organic EL element, preferably a hole transporting layer, the functional thin film laminated on the thin film and its cathode side. The barrier for charge transport between the organic element and the organic element becomes small, and the luminance characteristics of the organic element can be improved.
- Examples of materials used and methods for producing an OLED element using the charge transporting varnish of the present invention include the following, but are not limited thereto.
- 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 anode material is mainly composed of an organic material, the surface treatment may not be performed.
- the example of the manufacturing method of the OLED element which has a positive hole transport layer which consists of a thin film obtained from the charge transportable varnish of this invention is as follows.
- the charge transporting varnish of the present invention is applied to the anode substrate or, if necessary, the hole injection layer provided on the anode substrate and baked to produce a hole transport layer on the electrode.
- This is introduced into a vacuum deposition apparatus, and 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. Other metals constituting the metal anode include scandium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, gallium, yttrium, zirconium, niobium, molybdenum, ruthenium, rhodium, palladium, cadmium.
- 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-phenylphenolato) 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-spirobifluoren
- luminescent dopants examples include 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H, 5H, 11H-10-.
- Materials for forming the electron transport layer / hole block layer include 8-hydroxyquinolinolate-lithium, 2,2 ′, 2 ′′-(1,3,5-benztolyl) -tris (1-phenyl-1- H-benzimidazole), 2- (4-biphenyl) 5- (4-t-butylphenyl) -1,3,4-oxadiazole, 2,9-dimethyl-4,7-diphenyl-1,10- Phenanthroline, 4,7-diphenyl-1,10-phenanthroline, bis (2-methyl-8-quinolinolate) -4- (phenylphenolato) aluminum, 1,3-bis [2- (2,2′-bipyridine- 6-yl) -1,3,4-oxadiazo-5-yl] benzene, 6,6′-bis [5- (biphenyl-4-yl) -1,3,4-oxadiazo-2-yl] -2 , 2'- Pyridine, 3- (4-bi
- 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.
- Examples of the cathode material include aluminum, magnesium-silver alloy, aluminum-lithium alloy, lithium, sodium, potassium, cesium and the like.
- Examples of the material for forming the electron blocking layer include tris (phenylpyrazole) iridium.
- the charge transport material used for the hole transport layer a compound other than the hole transport polymer material is used among the charge transport materials exemplified above.
- the manufacturing method of the PLED element using the charge transportable varnish of this invention is not specifically limited, The following methods are mentioned.
- the hole transporting property formed by the charge transporting varnish of the present invention is formed by forming a light emitting polymer layer instead of performing vacuum deposition operation of the light emitting layer, the electron transporting layer, and the electron injection layer.
- a PLED element having a polymer layer can be produced.
- the charge transporting varnish of the present invention is applied to produce a positive hole transport layer by the above-described method.
- a light emitting polymer layer is sequentially formed thereon, and a cathode is further deposited to form a PLED element.
- the cathode and anode material to be used 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.
- the light-emitting polymer layer is formed by adding a solvent to a light-emitting polymer material or a material obtained by adding a dopant substance to the light-emitting polymer material, or after uniformly dispersing and applying it on the hole transport layer. And a method of forming a film by firing each.
- 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). And polyphenylene vinylene derivatives such as -PPV), polythiophene derivatives such as poly (3-alkylthiophene) (PAT), and polyvinylcarbazole (PVCz).
- PDAF poly (9,9-dialkylfluorene)
- MEH 2-methoxy-5- (2′-ethylhexoxy) -1,4-phenylenevinylene
- PVCz polyvinylcarbazole
- Examples of the solvent include toluene, xylene, chloroform, and the like.
- Examples of the dissolution or uniform dispersion method include methods such as stirring, heating and stirring, and ultrasonic dispersion.
- the application method is not particularly limited, and examples thereof include an inkjet method, a spray method, a dipping method, a spin coating method, a transfer printing method, a roll coating method, and a brush coating method.
- the application is preferably performed under an inert gas such as nitrogen or argon.
- Examples of the firing method include a method of heating in an oven or a hot plate under an inert gas or in a vacuum.
- Example 1-2 A charge transporting varnish was prepared in the same manner as in Example 1-1 except that the amount of charge transporting polymer (ADS250BE) used was 0.0251 g.
- This varnish was applied to an ITO substrate using a spin coater, dried at 80 ° C. for 1 minute, and then baked at 230 ° C. for 15 minutes in an air atmosphere to form a 30 nm uniform thin film (holes) on the ITO substrate. Injection layer) was formed.
- a glass substrate of 25 mm ⁇ 25 mm ⁇ 0.7 t in which indium tin oxide (ITO) is patterned on the surface with a film thickness of 150 nm is used, and an O 2 plasma cleaning apparatus (150 W, 30 seconds) before use. To remove impurities on the surface.
- ITO indium tin oxide
- Example 1-1 the charge transporting varnish obtained in Example 1-1 was applied on the thin film formed on the ITO substrate using a spin coater, and then baked at 150 ° C. for 10 minutes in an air atmosphere to be 30 nm. A uniform thin film (hole transport layer) was formed.
- CBP and Ir (PPy) 3 were co-deposited using a vapor deposition apparatus (degree of vacuum 1.0 ⁇ 10 ⁇ 5 Pa). In the co-evaporation, the deposition rate was controlled so that the concentration of Ir (PPy) 3 was 6%, and the layers were laminated to 40 nm.
- an organic EL element was obtained by sequentially laminating thin films of BAlq, lithium fluoride, and aluminum.
- the deposition rate was 0.2 nm / second for BAlq and aluminum and 0.02 nm / second for lithium fluoride, and the film thicknesses were 20 nm, 0.5 nm, and 100 nm, respectively.
- the characteristic was evaluated. Sealing was performed according to the following procedure. In a nitrogen atmosphere with an oxygen concentration of 2 ppm or less and a dew point of ⁇ 85 ° C.
- the organic EL element is placed between the sealing substrates, and the sealing substrate is adhesive (MORESCO Co., Ltd., Mores Moisture Cut WB90US (P)) Was pasted together.
- a water trapping 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.
- Example 2-2 Comparative Example 2
- An organic EL device was prepared in the same manner as in Example 2-1, except that the varnish obtained in Example 1-2 and Comparative Example 1 was used instead of the varnish obtained in Example 1-1. Manufactured.
- the organic EL device having a thin film obtained from the charge transporting varnish of the present invention has excellent luminance characteristics and current efficiency.
- Example 3-1 Measurement of ionization potential
- the varnish obtained in Example 1-1 was applied to a glass substrate of 25 mm ⁇ 25 mm ⁇ 0.7 t formed of indium tin oxide (ITO) so as to have a film thickness of 150 nm, and then was applied in an air atmosphere to 150 Baking at 10 ° C. for 10 minutes formed a uniform thin film of 30 nm. Before the substrate was used, impurities on the surface were removed by an O 2 plasma cleaning apparatus (150 W, 30 seconds). The ionization potential of the obtained thin film was measured using an atmospheric photoelectron spectrometer AC-3. Specific measurement methods and ionization potential determination methods are shown below.
- compressed air 0.5 to 0.7 MPa
- compressed nitrogen purity: 99.9% or more, pressure: 0.5 to 0.6 MPa
- the main body was connected to a personal computer, communication was established, the light quantity adjustment device was initialized, and the detector voltage was set.
- the light amount was set to 20 nW, and a light amount correction coefficient of 4.8 to 7.0 eV was measured.
- a sample was inserted, and a photoelectron yield of 4.8 to 7.0 eV was measured using the measured light amount correction coefficient.
- Example 3-2 Comparative Example 3
- the ionization potential was measured in the same manner as in Example 3-1, except that the varnish obtained in Example 1-2 and Comparative Example 1 was used instead of the varnish obtained in Example 1-1. did.
- the results are also shown in Table 2.
- the ionization potential of the thin film obtained from the charge transporting varnish of the present invention containing the organosilane compound is higher than that of the thin film obtained from the charge transporting varnish of the comparative example not containing the organosilane compound. You can see that it ’s big. Considering the results of Table 1 together, it can be seen that the luminance characteristics and current efficiency are improved when the value of the ionization potential is high (deep).
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Abstract
Description
この有機EL素子ではその性能を高める観点から複数の機能性薄膜が用いられるが、中でも正孔注入層や正孔輸送層は、陽極と発光層との電荷の授受を担い、有機EL素子の電圧駆動の低下および輝度向上を達成するために重要な機能を果たす。
なお、ポリスチレンスルホン酸やポリアニリン等の導電性ポリマーを含む組成物に、グリシドオキシプロピルトリメトキシシランや所定のシロキサン系物質を含めることで、当該組成物から得られる薄膜を備える有機EL素子の輝度特性や寿命を向上できることが報告されている(特許文献1,2参照)が、本発明で用いる有機シラン化合物を含む電荷輸送性ワニスに関する報告はない。
1. 電荷輸送性物質と、有機シラン化合物と、有機溶媒とを含み、前記有機シラン化合物が、予めアルコキシシラン化合物を加水分解縮合して調製された重量平均分子量500~10000の重合体であり、前記アルコキシシラン化合物が、式(1-1)および(1-2)で表されるアルコキシシラン化合物から選ばれる少なくとも1種を含むことを特徴とする電荷輸送性ワニス、
SiR1(OR2)3 (1-1)
SiR1 2(OR2)2 (1-2)
(式中、R1は、それぞれ独立に、Z1で置換された炭素数1~20のアルキル基、またはZ2で置換された炭素数6~20のアリール基を表し、R2は、それぞれ独立に、Z3で置換されていてもよい炭素数1~20のアルキル基を表し、Z1は、ハロゲン原子、シアノ基、ニトロ基、Z3で置換された炭素数1~20のアルコキシ基、Z3で置換された炭素数6~20のアリール基、またはZ3で置換された炭素数2~20のヘテロアリール基を表し、Z2は、ハロゲン原子、シアノ基、ニトロ基、またはZ3で置換された炭素数1~20のアルキル基を表し、Z3は、ハロゲン原子、シアノ基、またはニトロ基を表す。)
2. 前記アルコキシシラン化合物が、前記式(1-1)および式(1-2)で表されるアルコキシシラン化合物から選ばれる少なくとも1種と、式(2-1)~(2-3)で表されるアルコキシシラン化合物から選ばれる少なくとも1種とを含む1の電荷輸送性ワニス、
Si(OR3)4 (2-1)
SiR4 2(OR3)2 (2-2)
SiR4(OR3)3 (2-3)
(式中、R3は、それぞれ独立に、Z3で置換されていてもよい炭素数1~20のアルキル基を表し、R4は、それぞれ独立に、炭素数1~20のアルキル基、Z4で置換されていてもよい炭素数2~20のアルケニル基、Z4で置換されていてもよい炭素数2~20のアルキニル基、炭素数6~20のアリール基、またはZ5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、Z3は、前記と同じ意味を表し、Z4は、ハロゲン原子、ニトロ基、シアノ基、ヒドロキシル基、チオール基、Z6で置換されていてもよい炭素数6~20のアリール基、またはZ6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、Z5は、ハロゲン原子、ニトロ基、シアノ基、ヒドロキシル基、チオール基、Z6で置換されていてもよい炭素数1~20のアルキル基、Z6で置換されていてもよい炭素数1~20のアルケニル基、またはZ6で置換されていてもよい炭素数1~20のアルキニル基を表し、Z6は、ハロゲン原子、ニトロ基、シアノ基、ヒドロキシル基、またはチオール基を表す。)
3. 前記アルコキシシラン化合物が、前記式(1-1)で表されるアルコキシラン化合物と、前記式(2-1)で表されるアルコキシシラン化合物とを含む1または2の電荷輸送性ワニス、
4. 前記電荷輸送性物質が、アニリン誘導体である1~3のいずれかの電荷輸送性ワニス、
5. 1~4のいずれか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、
6. 5の電荷輸送性薄膜を有する有機エレクトロルミネッセンス素子、
7. 前記電荷輸送性薄膜が、正孔注入層または正孔輸送層である6の有機エレクトロルミネッセンス素子、
8. 1~4のいずれかの電荷輸送性ワニスを基材上に塗布し、溶媒を蒸発させることを特徴とする電荷輸送性薄膜の製造方法、
9. 5の電荷輸送性薄膜を用いることを特徴とする有機エレクトロルミネッセンス素子の製造方法、
10. 電荷輸送性物質と有機溶媒とを含む電荷輸送性ワニスから得られる電荷輸送性薄膜のイオン化ポテンシャル深化方法であって、前記電荷輸送性ワニス中に、式(1-1)および(1-2)で表されるアルコキシシラン化合物から選ばれる少なくとも1種を含むアルコキシシラン化合物を加水分解縮合して調製された重量平均分子量500~10000の重合体を添加することを特徴とする電荷輸送性薄膜のイオン化ポテンシャル深化方法、
SiR1(OR2)3 (1-1)
SiR1 2(OR2)2 (1-2)
(式中、R1は、それぞれ独立に、Z1で置換された炭素数1~20のアルキル基、またはZ2で置換された炭素数6~20のアリール基を表し、R2は、それぞれ独立に、Z3で置換されていてもよい炭素数1~20のアルキル基を表し、Z1は、ハロゲン原子、シアノ基、ニトロ基、Z3で置換された炭素数1~20のアルコキシ基、Z3で置換された炭素数6~20のアリール基、またはZ3で置換された炭素数2~20のヘテロアリール基を表し、Z2は、ハロゲン原子、シアノ基、ニトロ基、またはZ3で置換された炭素数1~20のアルキル基を表し、Z3は、ハロゲン原子、シアノ基、またはニトロ基を表す。)
11. 電荷輸送性物質を含む電荷輸送性薄膜のイオン化ポテンシャル深化方法であって、前記電荷輸送性薄膜作製時に、前記電荷輸送性物質とともに式(1-1)および(1-2)で表されるアルコキシシラン化合物から選ばれる少なくとも1種を含むアルコキシシラン化合物を加水分解縮合して調製された重量平均分子量500~10000の重合体を用い、前記電荷輸送性薄膜内に前記重合体を導入することを特徴とする電荷輸送性薄膜のイオン化ポテンシャル深化方法
SiR1(OR2)3 (1-1)
SiR1 2(OR2)2 (1-2)
(式中、R1は、それぞれ独立に、Z1で置換された炭素数1~20のアルキル基、またはZ2で置換された炭素数6~20のアリール基を表し、R2は、それぞれ独立に、Z3で置換されていてもよい炭素数1~20のアルキル基を表し、Z1は、ハロゲン原子、シアノ基、ニトロ基、Z3で置換された炭素数1~20のアルコキシ基、Z3で置換された炭素数6~20のアリール基、またはZ3で置換された炭素数2~20のヘテロアリール基を表し、Z2は、ハロゲン原子、シアノ基、ニトロ基、またはZ3で置換された炭素数1~20のアルキル基を表し、Z3は、ハロゲン原子、シアノ基、またはニトロ基を表す。)
を提供する。
また、本発明の電荷輸送性ワニスは、所定の有機シラン化合物を含むことから、これを含まないワニスを用いた場合と比較し、得られる薄膜のイオン化ポテンシャルが深くなり、その結果、当該薄膜とそれに接する陰極側の機能性薄膜との間の電荷輸送の障壁が低減されたものとなり得る。
この平坦性が良好で、好適なイオン化ポテンシャルを有する本発明の電荷輸送性薄膜を、有機EL素子の正孔注入層や正孔輸送層、好ましくは正孔輸送層に適用することで、素子の輝度特性の向上を図ることができる。
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。
なお、本発明の電荷輸送性薄膜は、コンデンサ電極保護膜、帯電防止膜、有機薄膜太陽電池の陽極バッファ層等への応用も期待される。
本発明に係る電荷輸送性ワニスは、電荷輸送性物質と、予めアルコキシシラン化合物を加水分解縮合して調製された重量平均分子量500~10000の重合体からなる有機シラン化合物と、有機溶媒とを含み、上記アルコキシシラン化合物が、式(1-1)および(1-2)で表されるアルコキシシラン化合物から選ばれる少なくとも1種を含むものであるが、重合体の分子量をより高めることを考慮すると、式(1-1)で表されるトリアルコキシシラン化合物を含むものが好ましい。
SiR1(OR2)3 (1-1)
SiR1 2(OR2)2 (1-2)
炭素数1~20のアルキル基としては、直鎖状、分岐鎖状、環状のいずれでもよく、例えば、メチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、イソブチル基、s-ブチル基、t-ブチル基、n-ペンチル基、n-ヘキシル基、n-ヘプチル基、n-オクチル基、n-ノニル基、n-デシル基等の炭素数1~20の直鎖または分岐鎖状アルキル基;シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基、シクロノニル基、シクロデシル基、ビシクロブチル基、ビシクロペンチル基、ビシクロヘキシル基、ビシクロヘプチル基、ビシクロオクチル基、ビシクロノニル基、ビシクロデシル基等の炭素数3~20の環状アルキル基などが挙げられる。
炭素数2~20のヘテロアリール基の具体例としては、2-チエニル基、3-チエニル基、2-フラニル基、3-フラニル基、2-オキサゾリル基、4-オキサゾリル基、5-オキサゾリル基、3-イソオキサゾリル基、4-イソオキサゾリル基、5-イソオキサゾリル基、2-チアゾリル基、4-チアゾリル基、5-チアゾリル基、3-イソチアゾリル基、4-イソチアゾリル基、5-イソチアゾリル基、2-イミダゾリル基、4-イミダゾリル基、2-ピリジル基、3-ピリジル基、4-ピリジル基等が挙げられる。
また、アリール基およびヘテロアリール基の炭素数は、好ましくは14以下であり、より好ましくは10以下であり、より一層好ましくは6以下である。
Z1およびZ2としては、ハロゲン原子が好ましく、フッ素原子が最適であり、Z3としては、R2においては存在しない(すなわち、非置換である)ことが好ましく、Z1およびZ2においてはハロゲン原子が好ましく、フッ素原子が最適である。
Z2で置換された炭素数6~20のアリール基としては、上記Z3で置換された炭素数6~20のアリール基で例示した基に加え、4-トリクロロメチルフェニル基、4-トリブロモメチルフェニル基、4-トリフルオロメチルフェニル基等のハロゲン化アルキル基を有するアリール基等が挙げられるが、フッ化アルキル基を有するアリール基が好ましい。
Si(OR3)4 (2-1)
SiR4 2(OR3)2 (2-2)
SiR4(OR3)3 (2-3)
その他、ハロゲン原子、炭素数1~20のアルキル基、炭素数6~20のアリール基、炭素数2~20のヘテロアリール基の具体例としては、上記と同様のものが挙げられる。
また、アリール基およびヘテロアリール基の炭素数は、好ましくは14以下であり、より好ましくは10以下であり、より一層好ましくは6以下である。
また、R4としては、炭素数1~20のアルキル基または炭素数6~20のアリール基が好ましく、炭素数1~10のアルキル基または炭素数6~14のアリール基がより好ましく、炭素数1~6のアルキル基または炭素数6~10のアリール基がより一層好ましく、炭素数1~4のアルキル基またはフェニル基がさらに好ましい。
なお、複数のR3は、すべて同一でも異なっていてもよく、複数のR4も、すべて同一でも異なっていてもよい。
また、Z4としては、ハロゲン原子、Z6で置換されていてもよいフェニル基、Z6で置換されていてもよいフラニル基が好ましく、ハロゲン原子がより好ましく、フッ素原子、または存在しないこと(すなわち、非置換であること)がより一層好ましい。
また、Z5としては、ハロゲン原子、Z6で置換されていてもよい炭素数1~20のアルキル基、Z6で置換されていてもよいフラニル基が好ましく、ハロゲン原子がより好ましく、フッ素原子、または存在しないこと(すなわち、非置換であること)がより一層好ましい。
そして、Z6としては、ハロゲン原子が好ましく、フッ素原子または存在しないこと(すなわち、非置換であること)がより好ましい。
上記式(2-2)で表される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等が挙げられる。
上記式(2-3)で表されるトリアルコキシシラン化合物の具体例としては、メチルトリメトキシシラン、メチルトリエトキシシラン、エチルトリメトキシシラン、エチルトリエトキシシラン、プロピルトリメトキシシラン、プロピルトリエトキシシラン、ブチルトリメトキシシラン、ブチルトリエトキシシラン、ペンチルトリメトキシシラン、ペンチルトリエトキシシラン、ヘプチルトリメトキシシラン、ヘプチルトリエトキシシラン、オクチルトリメトキシシラン、オクチルトリエトキシシラン、ドデシルトリメトキシシラン、ドデシルトリエトキシシラン、ヘキサデシルトリメトキシシラン、ヘキサデシルトリエトキシシラン、オクタデシルトリメトキシシラン、オクタデシルトリエトキシシラン、フェニルトリメトキシシラン、フェニルトリエトキシシラン、ビニルトリメトキシシラン、ビニルトリエトキシシラン、トリエトキシ-2-チエニルシラン、3-(トリエトキシシリル)フラン等が挙げられる。
加水分解の手法としては、特に限定されるものではなく一般的な手法を用いればよい。一例を挙げると、アルコキシシラン化合物を、水系溶媒中で20~100℃程度で1~24時間処理する手法が挙げられる。この際、酸または塩基を触媒として用いることもできる。
Y1は、互いに独立して、水素原子、Z7で置換されていてもよい、炭素数1~20のアルキル基、炭素数2~20のアルケニル基もしくは炭素数2~20のアルキニル基、またはZ8で置換されていてもよい、炭素数6~20のアリール基もしくは炭素数2~20のヘテロアリール基を表す。
なお、アルキル基、アルケニル基、アルキニル基、アリール基、およびヘテロアリール基の具体例としては、上記と同様のものが挙げられる。
Y2~Y13は、互いに独立して、Z7で置換されていてもよい、炭素数1~20のアルキル基、炭素数2~20のアルケニル基もしくは炭素数2~20のアルキニル基、またはZ8で置換されていてもよい、炭素数6~20のアリール基もしくは炭素数2~20のヘテロアリール基を表す。
Z8は、ハロゲン原子、ニトロ基、シアノ基、アミノ基、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、またはZ9で置換されていてもよい、炭素数1~20のアルキル基、炭素数2~20のアルケニル基もしくは炭素数2~20のアルキニル基である。
Z9は、ハロゲン原子、ニトロ基、シアノ基、アミノ基、アルデヒド基、水酸基、チオール基、スルホン酸基、またはカルボン酸基である。
なお、Lが2以上である場合、複数のR11は、互いに同一であっても異なっていてもよく、複数のR12も、互いに同一であっても異なっていてもよい。
また、置換基Z8は、ハロゲン原子、またはZ9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、またはZ9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、置換基Z9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。
また、アリール基およびヘテロアリール基の炭素数は、好ましくは14以下であり、より好ましくは10以下であり、より一層好ましくは6以下である。
正孔輸送性低分子材料としては、(トリフェニルアミン)ダイマー誘導体、[(トリフェニルアミン)ダイマー]スピロダイマー、N,N’-ビス(ナフタレン-1-イル)-N,N’-ビス(フェニル)-ベンジジン(α-NPD)、N,N’-ビス(ナフタレン-2-イル)-N,N’-ビス(フェニル)-ベンジジン、N,N’-ビス(3-メチルフェニル)-N,N’-ビス(フェニル)-ベンジジン、N,N’-ビス(3-メチルフェニル)-N,N’-ビス(フェニル)-9,9-スピロビフルオレン、N,N’-ビス(ナフタレン-1-イル)-N,N’-ビス(フェニル)-9,9-スピロビフルオレン、N,N’-ビス(3-メチルフェニル)-N,N’-ビス(フェニル)-9,9-ジメチル-フルオレン、N,N’-ビス(ナフタレン-1-イル)-N,N’-ビス(フェニル)-9,9-ジメチル-フルオレン、N,N’-ビス(3-メチルフェニル)-N,N’-ビス(フェニル)-9,9-ジフェニル-フルオレン、N,N’-ビス(ナフタレン-1-イル)-N,N’-ビス(フェニル)-9,9-ジフェニル-フルオレン、N,N’-ビス(ナフタレン-1-イル)-N,N’-ビス(フェニル)-2,2’-ジメチルベンジジン、2,2’,7,7’-テトラキス(N,N-ジフェニルアミノ)-9,9-スピロビフルオレン、9,9-ビス[4-(N,N-ビス-ビフェニル-4-イル-アミノ)フェニル]-9H-フルオレン、9,9-ビス[4-(N,N-ビス-ナフタレン-2-イル-アミノ)フェニル]-9H-フルオレン、9,9-ビス[4-(N-ナフタレン-1-イル-N-フェニルアミノ)-フェニル]-9H-フルオレン、2,2’,7,7’-テトラキス[N-ナフタレニル(フェニル)-アミノ]-9,9-スピロビフルオレン、N,N’-ビス(フェナントレン-9-イル)-N,N’-ビス(フェニル)-ベンジジン、2,2’-ビス[N,N-ビス(ビフェニル-4-イル)アミノ]-9,9-スピロビフルオレン、2,2’-ビス(N,N-ジフェニルアミノ)-9,9-スピロビフルオレン、ジ-[4-(N,N-ジ(p-トリル)アミノ)-フェニル]シクロヘキサン、2,2’,7,7’-テトラ(N,N-ジ(p-トリル))アミノ-9,9-スピロビフルオレン、N,N,N’,N’-テトラ-ナフタレン-2-イル-ベンジジン、N,N,N’,N’-テトラ-(3-メチルフェニル)-3,3’-ジメチルベンジジン、N,N’-ジ(ナフタレニル)-N,N’-ジ(ナフタレン-2-イル)-ベンジジン、N,N,N’,N’-テトラ(ナフタレニル)-ベンジジン、N,N’-ジ(ナフタレン-2-イル)-N,N’-ジフェニルベンジジン-1,4-ジアミン、N1,N4-ジフェニル-N1,N4-ジ(m-トリル)ベンゼン-1,4-ジアミン、N2,N2,N6,N6-テトラフェニルナフタレン-2,6-ジアミン、トリス(4-(キノリン-8-イル)フェニル)アミン、2,2’-ビス(3-(N,N-ジ(p-トリル)アミノ)フェニル)ビフェニル、4,4’,4”-トリス[3-メチルフェニル(フェニル)アミノ]トリフェニルアミン(m-MTDATA)、4,4’,4”-トリス[1-ナフチル(フェニル)アミノ]トリフェニルアミン(1-TNATA)等のトリアリールアミン類、5,5”-ビス-{4-[ビス(4-メチルフェニル)アミノ]フェニル}-2,2’:5’,2”-ターチオフェン(BMA-3T)等のオリゴチオフェン類などが挙げられる。
ドーパント物質としては、ワニスに使用する少なくとも一種の溶媒に溶解するものであれば特に限定されず、無機系のドーパント物質、有機系のドーパント物質のいずれも使用できる。
これら無機系および有機系のドーパント物質は、1種類単独で用いてもよく、2種類以上組み合わせて用いてもよい。
なお、これらの有機溶媒は、それぞれ単独で、または2種以上混合して用いることができる。
また、本発明における電荷輸送性ワニスの固形分濃度は、ワニスの粘度および表面張力等や、作製する薄膜の厚み等を勘案して適宜設定されるものではあるが、通常、0.1~10.0質量%程度であり、ワニスの塗布性を向上させることを考慮すると、好ましくは0.5~5.0質量%程度、より好ましくは1.0~3.0質量%程度である。なお、ここでいう固形分とは、本発明の電荷輸送性ワニスに含まれる電荷輸送性物質およびドーパント物質を意味する。
ワニスの塗布方法としては、特に限定されるものではなく、ディップ法、スピンコート法、転写印刷法、ロールコート法、刷毛塗り、インクジェット法、スプレー法、スリットコート法等が挙げられ、塗布方法に応じてワニスの粘度および表面張力を調節することが好ましい。
なお、焼成の際、より高い均一成膜性を発現させたり、基材上で反応を進行させたりする目的で、2段階以上の温度変化をつけてもよく、加熱は、例えば、ホットプレートやオーブン等、適当な機器を用いて行えばよい。
したがって、本発明の電荷輸送性薄膜を、有機EL素子の正孔注入層や正孔輸送層、好ましくは正孔輸送層に適用することで、当該薄膜とその陰極側に積層される機能性薄膜との間の電荷輸送の障壁が小さくなり、有機素子の輝度特性の向上を図ることができる。
使用する電極基板は、洗剤、アルコール、純水等による液体洗浄を予め行って浄化しておくことが好ましく、例えば、陽極基板では使用直前にUVオゾン処理、酸素-プラズマ処理等の表面処理を行うことが好ましい。ただし陽極材料が有機物を主成分とする場合、表面処理を行わなくともよい。
上記の方法により、陽極基板上、あるいは必要に応じて陽極基板上に設けられた正孔注入層上に本発明の電荷輸送性ワニスを塗布して焼成し、電極上に正孔輸送層を作製する。これを真空蒸着装置内に導入し、発光層、電子輸送層、電子輸送層/ホールブロック層、陰極金属を順次蒸着してOLED素子とする。なお、必要に応じて、発光層と正孔輸送層との間に電子ブロック層を設けてよい。
陽極材料としては、インジウム錫酸化物(ITO)、インジウム亜鉛酸化物(IZO)に代表される透明電極や、アルミニウムに代表される金属やこれらの合金等から構成される金属陽極が挙げられ、平坦化処理を行ったものが好ましい。高電荷輸送性を有するポリチオフェン誘導体やポリアニリン誘導体を用いることもできる。
なお、金属陽極を構成するその他の金属としては、スカンジウム、チタン、バナジウム、クロム、マンガン、鉄、コバルト、ニッケル、銅、亜鉛、ガリウム、イットリウム、ジルコニウム、ニオブ、モリブデン、ルテニウム、ロジウム、パラジウム、カドミウム、インジウム、スカンジウム、ランタン、セリウム、プラセオジム、ネオジム、プロメチウム、サマリウム、ユウロピウム、ガドリニウム、テルビウム、ジスプロシウム、ホルミウム、エルビウム、ツリウム、イッテルビウム、ハフニウム、タリウム、タングステン、レニウム、オスミウム、イリジウム、プラチナ、金、チタン、鉛、ビスマスやこれらの合金等が挙げられるが、これらに限定されるわけではない。
陰極材料としては、アルミニウム、マグネシウム-銀合金、アルミニウム-リチウム合金、リチウム、ナトリウム、カリウム、セシウム等が挙げられる。
電子ブロック層を形成する材料としては、トリス(フェニルピラゾール)イリジウム等が挙げられる。
なお、正孔輸送層に用いる電荷輸送性物質としては、先に例示した電荷輸送性物質の中で、正孔輸送性高分子材料以外の化合物が用いられる。
上記OLED素子作製において、発光層、電子輸送層、電子注入層の真空蒸着操作を行う代わりに、発光性高分子層を形成することによって本発明の電荷輸送性ワニスによって形成される正孔輸送性高分子層を有するPLED素子を作製することができる。
具体的には、陽極基板あるいは陽極基板上に必要に応じて形成された正孔注入層上に、本発明の電荷輸送性ワニスを塗布して上記の方法により正孔輸送層を作製し、その上に発光性高分子層を順次形成し、さらに陰極を蒸着してPLED素子とする。
発光性高分子層の形成法としては、発光性高分子材料、またはこれにドーパント物質を加えた材料に溶媒を加えて溶解するか、均一に分散し、正孔輸送層の上に塗布した後、それぞれ焼成することで成膜する方法が挙げられる。
なお、正孔輸送層に用いる電荷輸送性物質としては、先に例示した正孔輸送性高分子材料が用いられる。
塗布方法としては、特に限定されるものではなく、インクジェット法、スプレー法、ディップ法、スピンコート法、転写印刷法、ロールコート法、刷毛塗り等が挙げられる。なお、塗布は、窒素、アルゴン等の不活性ガス下で行うことが好ましい。
焼成する方法としては、不活性ガス下または真空中、オーブンまたはホットプレートで加熱する方法が挙げられる。
(1)分子量測定:昭和電工(株)製、常温ゲル浸透クロマトグラフィー(GPC)装置(GPC-101)およびShodex製カラム(KD-803L)
(測定条件)
・カラム温度:40℃
・溶離液:テトラヒドロフラン(THF),10ml/L
・流速:1.0ml/分
・検量線作成用標準サンプル:昭和電工(株)製、SL-105,標準ポリスチレン(分子量約580,2970,7200,19900,52400)
(2)1H-NMR測定: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)イオン化ポテンシャルの測定:理研計器(株)製、大気中光電子分光装置AC-3
[合成例1]有機シラン化合物の合成
温度計および還流管を備え付けた200mLの四つ口反応フラスコ中で、ヘキシレングリコール18.4g、ブチルセロソルブ6.1g、テトラエトキシシラン23.3g、および3,3,3-トリフルオロプロピルトリメトキシシラン10.5gを混合し、アルコキシシランモノマーの溶液を調製した。
この溶液に、予めヘキシレングリコール9.2g、ブチルセロソルブ3.1g、水8.6gおよび触媒として蓚酸0.7gを混合した溶液を、室温下で30分かけて滴下し、さらに室温で30分撹拌した。その後、オイルバスを用いて加熱して1時間還流させた後、放冷して、SiO2換算濃度が12質量%のポリシロキサン溶液を得た。
得られたポリシロキサンの数平均分子量は2,500であり、重量平均分子量は3,500であった。
なお、得られたポリシロキサン溶液10.0g、ヘキシレングリコール42.0g、およびブチルセロソルブ14.0gを混合し、SiO2換算濃度が5質量%のポリシロキサン溶液を調製し、このポリシロキサン溶液を電荷輸送性ワニスの調製に用いた。
[実施例1-1]
窒素雰囲気下で、電荷輸送性ポリマーであるポリ[(9,9-ジヘキシルフルオレニル-2,7-ジイル)-co-(N,N’-ビス{p-ブチルフェニル}-1,4-ジアミノフェニレン)](ADS250BE,American Dye Source,Inc製、以下同様)0.05gと、合成例1で得られたポリシロキサン溶液0.0151gと、トルエン10gとをよく混合して、電荷輸送性ワニスを調製した。
電荷輸送性ポリマー(ADS250BE)の使用量を0.0251gとした以外は、実施例1-1と同様の方法で電荷輸送性ワニスを調製した。
窒素雰囲気下で、電荷輸送性ポリマー(ADS250BE)0.05gと、トルエン10gとをよく混合して、電荷輸送性ワニスを調製した。
[実施例2-1]
まず、窒素雰囲気下で、国際公開第2013/084664号記載の方法に従って合成した式(A1)で表されるアニリン誘導体0.165gと、国際公開第2006/025342号記載の方法に従って合成した式(S1)で表されるアリールスルホン酸0.325gとを、1,3-ジメチル-2-イミダゾリジノン8.0gに溶解させた。そこへ、シクロヘキサノール12.0gおよびプロピレングリコール4.0gを加えて撹拌し、さらにそこへ3,3,3-トリフルオロプロピルトリメトキシシラン0.016gおよびフェニルトリメトキシシラン0.033gを溶解させて撹拌して正孔注入層形成用ワニスを得た。
次いで、ITO基板上に形成された薄膜の上に、スピンコーターを用いて実施例1-1で得られた電荷輸送性ワニスを塗布した後、大気雰囲気下、150℃で10分間焼成し、30nmの均一な薄膜(正孔輸送層)を形成した。
その上に、蒸着装置(真空度1.0×10-5Pa)を用いてCBPとIr(PPy)3を共蒸着した。共蒸着はIr(PPy)3の濃度が6%になるように蒸着レートをコントロールし、40nm積層させた。次いで、BAlq、フッ化リチウムおよびアルミニウムの薄膜を順次積層して有機EL素子を得た。この際、蒸着レートは、BAlqおよ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20nm、0.5nmおよび100nm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((株)MORESCO製、モレスコモイスチャーカット WB90US(P))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1-1で得られたワニスの代わりに、それぞれ、実施例1-2、比較例1で得られたワニスを用いた以外は、実施例2-1と同様の方法で有機EL素子を製造した。
[実施例3-1]
実施例1-1で得られたワニスをインジウム錫酸化物(ITO)が膜厚150nmとなるように成膜された25mm×25mm×0.7tのガラス基板に塗布した後、大気雰囲気下、150℃で10分間焼成し、30nmの均一な薄膜を形成した。基板は使用前に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去した。
得られた薄膜について、大気中光電子分光装置AC-3を用いてイオン化ポテンシャルを測定した。具体的な測定方法とイオン化ポテンシャルの決定方法を下記に示す。
まず、装置本体内に圧搾空気(0.5~0.7MPa)と圧搾窒素(純度:99.9%以上、圧力:0.5~0.6MPa)を供給し、装置を暖機した。その後、本体とパソコンを接続し、通信の確立、光量調節装置の初期化、検知器電圧設定を行った。次に、光量を20nWに設定し、4.8~7.0eVの光量補正係数を測定した。続いて、サンプルを挿入し、測定した光量補正係数を用いて4.8~7.0eVの光電子収率を測定した。測定終了後、横軸が照射光のエネルギー、縦軸が光電子収率実測値の平方根のグラフを作成し、最小二乗法で得られた外挿直線とグランドレベルとの交点からイオン化ポテンシャルを決定した。結果を表2に示す。
実施例1-1で得られたワニスの代わりに、それぞれ、実施例1-2、比較例1で得られたワニスを用いた以外は、実施例3-1と同様の方法でイオン化ポテンシャルを測定した。結果を併せて表2に示す。
Claims (11)
- 電荷輸送性物質と、有機シラン化合物と、有機溶媒とを含み、
前記有機シラン化合物が、予めアルコキシシラン化合物を加水分解縮合して調製された重量平均分子量500~10000の重合体であり、
前記アルコキシシラン化合物が、式(1-1)および(1-2)で表されるアルコキシシラン化合物から選ばれる少なくとも1種を含むことを特徴とする電荷輸送性ワニス。
SiR1(OR2)3 (1-1)
SiR1 2(OR2)2 (1-2)
(式中、R1は、それぞれ独立に、Z1で置換された炭素数1~20のアルキル基、またはZ2で置換された炭素数6~20のアリール基を表し、
R2は、それぞれ独立に、Z3で置換されていてもよい炭素数1~20のアルキル基を表し、
Z1は、ハロゲン原子、シアノ基、ニトロ基、Z3で置換された炭素数1~20のアルコキシ基、Z3で置換された炭素数6~20のアリール基、またはZ3で置換された炭素数2~20のヘテロアリール基を表し、
Z2は、ハロゲン原子、シアノ基、ニトロ基、またはZ3で置換された炭素数1~20のアルキル基を表し、
Z3は、ハロゲン原子、シアノ基、またはニトロ基を表す。) - 前記アルコキシシラン化合物が、前記式(1-1)および式(1-2)で表されるアルコキシシラン化合物から選ばれる少なくとも1種と、式(2-1)~(2-3)で表されるアルコキシシラン化合物から選ばれる少なくとも1種類とを含む請求項1記載の電荷輸送性ワニス。
Si(OR3)4 (2-1)
SiR4 2(OR3)2 (2-2)
SiR4(OR3)3 (2-3)
(式中、R3は、それぞれ独立に、Z3で置換されていてもよい炭素数1~20のアルキル基を表し、
R4は、それぞれ独立に、炭素数1~20のアルキル基、Z4で置換されていてもよい炭素数2~20のアルケニル基、Z4で置換されていてもよい炭素数2~20のアルキニル基、炭素数6~20のアリール基、またはZ5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、
Z3は、前記と同じ意味を表し、
Z4は、ハロゲン原子、ニトロ基、シアノ基、ヒドロキシル基、チオール基、Z6で置換されていてもよい炭素数6~20のアリール基、またはZ6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、
Z5は、ハロゲン原子、ニトロ基、シアノ基、ヒドロキシル基、チオール基、Z6で置換されていてもよい炭素数1~20のアルキル基、Z6で置換されていてもよい炭素数1~20のアルケニル基、またはZ6で置換されていてもよい炭素数1~20のアルキニル基を表し、
Z6は、ハロゲン原子、ニトロ基、シアノ基、ヒドロキシル基、またはチオール基を表す。) - 前記アルコキシシラン化合物が、前記式(1-1)で表されるアルコキシラン化合物と、前記式(2-1)で表されるアルコキシシラン化合物とを含む請求項1または2記載の電荷輸送性ワニス。
- 前記電荷輸送性物質が、アニリン誘導体である請求項1~3のいずれか1項記載の電荷輸送性ワニス。
- 請求項1~4のいずれか1項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5記載の電荷輸送性薄膜を有す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、正孔注入層または正孔輸送層である請求項6記載の有機エレクトロルミネッセンス素子。
- 請求項1~4のいずれか1項記載の電荷輸送性ワニスを基材上に塗布し、溶媒を蒸発させることを特徴とする電荷輸送性薄膜の製造方法。
- 請求項5記載の電荷輸送性薄膜を用いることを特徴とする有機エレクトロルミネッセンス素子の製造方法。
- 電荷輸送性物質と有機溶媒とを含む電荷輸送性ワニスから得られる電荷輸送性薄膜のイオン化ポテンシャル深化方法であって、
前記電荷輸送性ワニス中に、式(1-1)および(1-2)で表されるアルコキシシラン化合物から選ばれる少なくとも1種を含むアルコキシシラン化合物を加水分解縮合して調製された重量平均分子量500~10000の重合体を添加することを特徴とする電荷輸送性薄膜のイオン化ポテンシャル深化方法。
SiR1(OR2)3 (1-1)
SiR1 2(OR2)2 (1-2)
(式中、R1は、それぞれ独立に、Z1で置換された炭素数1~20のアルキル基、またはZ2で置換された炭素数6~20のアリール基を表し、
R2は、それぞれ独立に、Z3で置換されていてもよい炭素数1~20のアルキル基を表し、
Z1は、ハロゲン原子、シアノ基、ニトロ基、Z3で置換された炭素数1~20のアルコキシ基、Z3で置換された炭素数6~20のアリール基、またはZ3で置換された炭素数2~20のヘテロアリール基を表し、
Z2は、ハロゲン原子、シアノ基、ニトロ基、またはZ3で置換された炭素数1~20のアルキル基を表し、
Z3は、ハロゲン原子、シアノ基、またはニトロ基を表す。) - 電荷輸送性物質を含む電荷輸送性薄膜のイオン化ポテンシャル深化方法であって、
前記電荷輸送性薄膜作製時に、前記電荷輸送性物質とともに式(1-1)および(1-2)で表されるアルコキシシラン化合物から選ばれる少なくとも1種を含むアルコキシシラン化合物を加水分解縮合して調製された重量平均分子量500~10000の重合体を用い、前記電荷輸送性薄膜内に前記重合体を導入することを特徴とする電荷輸送性薄膜のイオン化ポテンシャル深化方法。
SiR1(OR2)3 (1-1)
SiR1 2(OR2)2 (1-2)
(式中、R1は、それぞれ独立に、Z1で置換された炭素数1~20のアルキル基、またはZ2で置換された炭素数6~20のアリール基を表し、
R2は、それぞれ独立に、Z3で置換されていてもよい炭素数1~20のアルキル基を表し、
Z1は、ハロゲン原子、シアノ基、ニトロ基、Z3で置換された炭素数1~20のアルコキシ基、Z3で置換された炭素数6~20のアリール基、またはZ3で置換された炭素数2~20のヘテロアリール基を表し、
Z2は、ハロゲン原子、シアノ基、ニトロ基、またはZ3で置換された炭素数1~20のアルキル基を表し、
Z3は、ハロゲン原子、シアノ基、またはニトロ基を表す。)
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US15/313,399 US10090477B2 (en) | 2014-05-23 | 2015-05-20 | Charge-transporting varnish |
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WO2022018572A1 (ja) * | 2020-07-24 | 2022-01-27 | 株式会社半導体エネルギー研究所 | 発光デバイス、発光装置、電子機器および照明装置 |
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JP6627755B2 (ja) | 2020-01-08 |
TW201610038A (zh) | 2016-03-16 |
KR20170013899A (ko) | 2017-02-07 |
EP3147960A4 (en) | 2018-01-03 |
TWI656182B (zh) | 2019-04-11 |
CN106463631B (zh) | 2018-09-04 |
CN106463631A (zh) | 2017-02-22 |
EP3147960A1 (en) | 2017-03-29 |
US20170186982A1 (en) | 2017-06-29 |
KR102445034B1 (ko) | 2022-09-20 |
JPWO2015178407A1 (ja) | 2017-04-20 |
US10090477B2 (en) | 2018-10-02 |
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