JPWO2016117522A1 - 電荷輸送性ワニス、電荷輸送性薄膜及び有機エレクトロルミネッセンス素子 - Google Patents
電荷輸送性ワニス、電荷輸送性薄膜及び有機エレクトロルミネッセンス素子 Download PDFInfo
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- JPWO2016117522A1 JPWO2016117522A1 JP2016570635A JP2016570635A JPWO2016117522A1 JP WO2016117522 A1 JPWO2016117522 A1 JP WO2016117522A1 JP 2016570635 A JP2016570635 A JP 2016570635A JP 2016570635 A JP2016570635 A JP 2016570635A JP WO2016117522 A1 JPWO2016117522 A1 JP WO2016117522A1
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- NJWJVPXCXKIBJD-QURGRASLSA-N n,n-diphenyl-6-[(e)-2-[4-(n-phenylanilino)phenyl]ethenyl]naphthalen-2-amine Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1/C=C/C(C=C1C=C2)=CC=C1C=C2N(C=1C=CC=CC=1)C1=CC=CC=C1 NJWJVPXCXKIBJD-QURGRASLSA-N 0.000 description 1
- ZJFKMIYGRJGWIB-UHFFFAOYSA-N n-[3-methyl-4-[2-methyl-4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound CC1=CC(N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)=CC=C1C(C(=C1)C)=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 ZJFKMIYGRJGWIB-UHFFFAOYSA-N 0.000 description 1
- CLTPAQDLCMKBIS-UHFFFAOYSA-N n-[4-[4-(dinaphthalen-1-ylamino)phenyl]phenyl]-n-naphthalen-1-ylnaphthalen-1-amine Chemical compound C1=CC=C2C(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 CLTPAQDLCMKBIS-UHFFFAOYSA-N 0.000 description 1
- QKCGXXHCELUCKW-UHFFFAOYSA-N n-[4-[4-(dinaphthalen-2-ylamino)phenyl]phenyl]-n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C=C4C=CC=CC4=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=C21 QKCGXXHCELUCKW-UHFFFAOYSA-N 0.000 description 1
- BLFVVZKSHYCRDR-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-2-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-2-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 BLFVVZKSHYCRDR-UHFFFAOYSA-N 0.000 description 1
- LBFXFIPIIMAZPK-UHFFFAOYSA-N n-[4-[4-(n-phenanthren-9-ylanilino)phenyl]phenyl]-n-phenylphenanthren-9-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C2=CC=CC=C2C=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C3=CC=CC=C3C=2)C=C1 LBFXFIPIIMAZPK-UHFFFAOYSA-N 0.000 description 1
- PKQHEBAYOGHIPX-UHFFFAOYSA-N n-[4-[9-[4-(dinaphthalen-2-ylamino)phenyl]fluoren-9-yl]phenyl]-n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(N(C=3C=C4C=CC=CC4=CC=3)C3=CC=C(C=C3)C3(C=4C=CC(=CC=4)N(C=4C=C5C=CC=CC5=CC=4)C=4C=C5C=CC=CC5=CC=4)C4=CC=CC=C4C=4C3=CC=CC=4)=CC=C21 PKQHEBAYOGHIPX-UHFFFAOYSA-N 0.000 description 1
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- 229940017144 n-butyl lactate Drugs 0.000 description 1
- 125000006610 n-decyloxy group Chemical group 0.000 description 1
- ZJBIJOORRHXJDN-UHFFFAOYSA-N n-ethyl-n,2-dimethylpropanamide Chemical compound CCN(C)C(=O)C(C)C ZJBIJOORRHXJDN-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
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- RYZPDEZIQWOVPJ-UHFFFAOYSA-N n-naphthalen-1-yl-n-[4-[4-[naphthalen-1-yl(naphthalen-2-yl)amino]phenyl]phenyl]naphthalen-2-amine Chemical compound C1=CC=C2C(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C4=CC=CC=C4C=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=CC2=C1 RYZPDEZIQWOVPJ-UHFFFAOYSA-N 0.000 description 1
- 125000006609 n-nonyloxy group Chemical group 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 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 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
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- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
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- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- MQZFZDIZKWNWFX-UHFFFAOYSA-N osmium(2+) Chemical compound [Os+2] MQZFZDIZKWNWFX-UHFFFAOYSA-N 0.000 description 1
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 1
- GXOHBWLPQHTYPF-UHFFFAOYSA-N pentyl 2-hydroxypropanoate Chemical compound CCCCCOC(=O)C(C)O GXOHBWLPQHTYPF-UHFFFAOYSA-N 0.000 description 1
- CFNJLPHOBMVMNS-UHFFFAOYSA-N pentyl butyrate Chemical compound CCCCCOC(=O)CCC CFNJLPHOBMVMNS-UHFFFAOYSA-N 0.000 description 1
- TWSRVQVEYJNFKQ-UHFFFAOYSA-N pentyl propanoate Chemical compound CCCCCOC(=O)CC TWSRVQVEYJNFKQ-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
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- 238000009832 plasma treatment Methods 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000734 polysilsesquioxane polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- VQMWBBYLQSCNPO-UHFFFAOYSA-N promethium atom Chemical compound [Pm] VQMWBBYLQSCNPO-UHFFFAOYSA-N 0.000 description 1
- KIWATKANDHUUOB-UHFFFAOYSA-N propan-2-yl 2-hydroxypropanoate Chemical compound CC(C)OC(=O)C(C)O KIWATKANDHUUOB-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 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
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 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
- 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
- QJHDFBAAFGELLO-UHFFFAOYSA-N sec-butyl butyrate Chemical compound CCCC(=O)OC(C)CC QJHDFBAAFGELLO-UHFFFAOYSA-N 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
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000010561 standard procedure Methods 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
- FVRNDBHWWSPNOM-UHFFFAOYSA-L strontium fluoride Chemical compound [F-].[F-].[Sr+2] FVRNDBHWWSPNOM-UHFFFAOYSA-L 0.000 description 1
- 229910001637 strontium fluoride Inorganic materials 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- IXXMVXXFAJGOQO-UHFFFAOYSA-N tert-butyl 2-hydroxypropanoate Chemical compound CC(O)C(=O)OC(C)(C)C IXXMVXXFAJGOQO-UHFFFAOYSA-N 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- TWBUVVYSQBFVGZ-UHFFFAOYSA-N tert-butyl butanoate Chemical compound CCCC(=O)OC(C)(C)C TWBUVVYSQBFVGZ-UHFFFAOYSA-N 0.000 description 1
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 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
- NRTLTGGGUQIRRT-UHFFFAOYSA-N triethylazanium;bromide Chemical compound [Br-].CC[NH+](CC)CC NRTLTGGGUQIRRT-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-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
- 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
- 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
- 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
- 238000001771 vacuum deposition 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
- 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
- 239000003643 water by type Substances 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
-
- 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
- H10K85/60—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
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/76—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and etherified hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
- H10K50/155—Hole transporting layers comprising dopants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Optics & Photonics (AREA)
Abstract
Description
1.式(1)で表されるアリールアミン誘導体からなる電荷輸送性物質、ドーパント及び有機溶媒を含むことを特徴とする電荷輸送性ワニス。
Rは、互いに独立して、ハロゲン原子、ニトロ基、シアノ基、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、Z1で置換されていてもよい炭素数1〜20のアルコキシ基、Z1で置換されていてもよい炭素数2〜20のアルケニルオキシ基、又はZ1で置換されていてもよい炭素数2〜20のアルキニルオキシ基を表し;
Z1は、ハロゲン原子、ニトロ基、シアノ基、Z2で置換されていてもよい炭素数6〜20のアリール基、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、Z2で置換されていてもよい炭素数1〜20のアルコキシ基、Z2で置換されていてもよい炭素数2〜20のアルケニルオキシ基、Z2で置換されていてもよい炭素数2〜20のアルキニルオキシ基、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;
Z2は、ハロゲン原子、ニトロ基又はシアノ基を表し;
nは、互いに独立して、0〜5の整数であり、mは、互いに独立して、0〜4の整数であり、pは、互いに独立して、0〜3の整数である。]
2.R1及びR2が、ともに炭素数1〜20のアルキル基又はともに少なくとも1つのエーテル構造を含む炭素数2〜20のアルキル基である1の電荷輸送性ワニス。
3.n、m及びpが、全て0である1又は2の電荷輸送性ワニス。
4.前記ドーパントがヘテロポリ酸である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備える有機EL素子。
7.前記電荷輸送性薄膜が正孔注入層である6の有機EL素子。
8.式(1')で表されるアリールアミン誘導体。
Rは、互いに独立して、ハロゲン原子、ニトロ基、シアノ基、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、Z1で置換されていてもよい炭素数1〜20のアルコキシ基、Z1で置換されていてもよい炭素数2〜20のアルケニルオキシ基、又はZ1で置換されていてもよい炭素数2〜20のアルキニルオキシ基を表し;
Z1は、ハロゲン原子、ニトロ基、シアノ基、Z2で置換されていてもよい炭素数6〜20のアリール基、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、Z2で置換されていてもよい炭素数1〜20のアルコキシ基、Z2で置換されていてもよい炭素数2〜20のアルケニルオキシ基、Z2で置換されていてもよい炭素数2〜20のアルキニルオキシ基、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;
Z2は、ハロゲン原子、ニトロ基又はシアノ基を表し;
nは、互いに独立して、0〜5の整数であり、mは、互いに独立して、0〜4の整数であり、pは、互いに独立して、0〜3の整数である。]
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、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。
本発明の電荷輸送性ワニスは、下記式(1)で表されるアリールアミン誘導体からなる電荷輸送性物質を含む。なお、本発明において、電荷輸送性とは、導電性と同義であり、正孔輸送性と同義である。電荷輸送性物質は、それ自体に電荷輸送性があるものでもよく、電子受容性物質と共に用いた際に電荷輸送性があるものでもよい。電荷輸送性ワニスは、それ自体に電荷輸送性があるものでもよく、それにより得られる固形膜が電荷輸送性を有するものでもよい。
−(RAO)r−RB (A)
−(CH2CH2O)r−CH3 (B)
(式中、RAは炭素数1〜4の直鎖状又は分岐状のアルキレン基を表し、RBは炭素数1〜[20−(RAの炭素数)×r]の直鎖状又は分岐状のアルキル基を表し、rは1〜9の整数である。rは、ドーパントとの相溶性の観点から、好ましくは2以上、より好ましくは3以上であり、原料化合物の入手容易性の観点から、好ましくは5以下、より好ましくは4以下である。)
-CH2CH2O(CH2)5CH3、-CH2CH2OCH(CH3)(CH2)3CH3、-CH2CH2OCH2CH(CH3)(CH2)2CH3、-CH2CH2O(CH2)2CH(CH3)CH2CH3、-CH2CH2O(CH2)3CH(CH3)2、-CH2CH2OC(CH3)2(CH2)2CH3、-CH2CH2OCH(CH2CH3)(CH2)2CH3、-CH2CH2OC(CH3)2CH(CH3)2、-CH2CH2O(CH2)6CH3、-CH2CH2O(CH2)7CH3、-CH2CH2OCH2CH(CH2CH3)(CH2)3CH3、-CH2CH2O(CH2)8CH3、-CH2CH2O(CH2)9CH3、-CH2CH2O(CH2)10CH3、-CH2CH2O(CH2)11CH3、-CH2CH2O(CH2)12CH3、-CH2CH2O(CH2)13CH3、-CH2CH2O(CH2)14CH3、-CH2CH2O(CH2)15CH3、-CH2CH2O(CH2)16CH3、-CH2CH2O(CH2)17CH3、-CH2CH2CH2OCH3、-CH2CH2CH2OCH2CH3、-CH2CH2CH2O(CH2)2CH3、-CH2CH2CH2OCH(CH3)2、-CH2CH2CH2O(CH2)3CH3、-CH2CH2CH2OCH2CH(CH3)2、-CH2CH2CH2OC(CH3)3、-CH2CH2CH2O(CH2)4CH3、-CH2CH2CH2OCH(CH3)(CH2)2CH3、-CH2CH2CH2OCH2CH(CH3)2、-CH2CH2CH2O(CH2)2CH(CH3)2、-CH2CH2CH2OC(CH3)3、-CH2CH2CH2OCH(CH3)(CH2)3CH3、-CH2CH2CH2O(CH2)5CH3、-CH2CH2CH2OCH(CH3)(CH2)3CH3、-CH2CH2CH2OCH2CH(CH3)(CH2)2CH3、-CH2CH2CH2O(CH2)2CH(CH3)CH2CH3、-CH2CH2CH2O(CH2)3CH(CH3)2、-CH2CH2CH2OC(CH3)2(CH2)2CH3、-CH2CH2CH2OCH(CH2CH3)(CH2)2CH3、-CH2CH2CH2OC(CH3)2CH(CH3)2、-CH2CH2CH2O(CH2)6CH3、-CH2CH2CH2O(CH2)7CH3、-CH2CH2CH2OCH2CH(CH2CH3)(CH2)3CH3、-CH2CH2OCH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH3、-CH2CH2CH2OCH2CH2CH2OCH3、-CH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH3、-CH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH3、-CH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH3、-CH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH3、-CH2CH2CH2CH2OCH2CH2CH2CH2OCH2CH2CH2CH2OCH3、-CH2CH2CH2CH2OCH2CH2CH2CH2OCH2CH2CH2CH2OCH2CH2CH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH3、-CH2CH2OCH2CH2OCH2CH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH3、-CH2CH2CH2O(CH2)8CH3、-CH2CH2CH2O(CH2)9CH3、-CH2CH2CH2O(CH2)10CH3、-CH2CH2CH2O(CH2)11CH3、-CH2CH2CH2O(CH2)12CH3、-CH2CH2CH2O(CH2)13CH3、-CH2CH2CH2O(CH2)14CH3、-CH2CH2CH2O(CH2)15CH3、-CH2CH2CH2O(CH2)16CH3等が挙げられる。
前記アリールアミン誘導体は、下記合成スキームAに従って式(1')で表される中間体を合成した後、公知のカップリング反応を利用して合成することができる。
本発明の電荷輸送性ワニスは、ドーパントを含む。ドーパントとしては、特に限定されず、無機系ドーパント、有機系ドーパントのいずれも用いることができる。
本発明の電荷輸送性ワニスに含まれる有機溶媒は、前記アリールアミン誘導体とドーパントとを良好に溶解するものである限り特に限定されないが、アミド類を含むことが好ましく、下記式(2)で表される酸アミド誘導体を含むことがより好ましい。
N−メチルホルムアミド、N,N−ジメチルホルムアミド、N,N−ジエチルホルムアミド、N−メチルアセトアミド、N,N−ジメチルアセトアミド、N−メチルプロピオンアミド、1,3−ジメチル−2−イミダゾリジノン、N−メチルピロリドン等のアミド類;
ジエチレングリコール、トリエチレングリコール、テトラエチレングリコール、ジプロピレングリコール、1,2−エタンジオール(エチレングリコール)、1,2−プロパンジオール(プロピレングリコール)、1,2−ブタンジオール、2,3−ブタンジオール、1,3−ブタンジオール、1,4−ブタンジオール、1,5−ペンタンジオール、2−メチル−2,4−ペンタンジオール(ヘキシレングリコール)、1,3−オクチレングリコール、3,6−オクチレングリコール等のグリコール類;
グリセリン等のトリオール類;
エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノプロピルエーテル、エチレングリコールモノイソプロピルエーテル、エチレングリコールモノブチルエーテル、エチレングリコールモノイソブチルエーテル、エチレングリコールモノヘキシルエーテル等のエチレングリコールモノアルキルエーテル類、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノイソプロピルエーテル、プロピレングリコールモノブチルエーテル、プロピレングリコールモノイソブチルエーテル、プロピレングリコールモノヘキシルエーテル等のプロピレングリコールモノアルキルエーテル類等のアルキレングリコールモノアルキルエーテル類;
エチレングリコールモノフェニルエーテル等のエチレングリコールモノアリールエーテル類、プロピレングリコールモノフェニルエーテル等のプロピレングリコールモノアリールエーテル類等のアルキレングリコールモノアリールエーテル類;
エチレングリコールモノベンジルエーテル等のエチレングリコールモノアラルキルエーテル類、プロピレングリコールモノベンジルエーテル等のプロピレングリコールモノアラルキルエーテル類等のアルキレングリコールモノアラルキルエーテル類;
エチレングリコールブトキシエチルエーテル等のエチレングリコールアルコキシアルキルエーテル類、プロピレングリコールブトキシエチルエーテル等のプロピレングリコールアルコキシアルキルエーテル類等のアルキレングリコールアルコキシアルキルエーテル類;
エチレングリコールジメチルエーテル、エチレングリコールジエチルエーテル、エチレングリコールジプロピルエーテル、エチレングリコールジイソプロピルエーテル、エチレングリコールジブチルエーテル等のエチレングリコールジアルキルエーテル類、プロピレングリコールジメチルエーテル、プロピレングリコールジエチルエーテル、プロピレングリコールジプロピルエーテル、プロピレングリコールジイソプロピルエーテル、プロピレングリコールジブチルエーテル等のプロピレングリコールジアルキルエーテル類等のアルキレングリコールジアルキルエーテル類;
エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノプロピルエーテルアセテート、エチレングリコールモノイソプロピルエーテルアセテート、エチレングリコールモノブチルエーテルアセテート等のエチレングリコールモノアルキルエーテルアセテート類、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノプロピルエーテルアセテート、プロピレングリコールモノイソプロピルエーテルアセテート、プロピレングリコールモノブチルエーテルアセテート等のプロピレングリコールモノアルキルエーテルアセテート類等のアルキレングリコールモノアルキルエーテルアセテート類;
エチレングリコールモノアセテート等のエチレングリコールモノアセテート類、プロピレングリコールモノアセテート等のプロピレングリコールモノアセテート類等のアルキレングリコールモノアセテート類;
エチレングリコールジアセテート等のエチレングリコールジアセテート類、プロピレングリコールジアセテート等のプロピレングリコールジアセテート類等のアルキレングリコールジアセテート類;
ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノプロピルエーテル、ジエチレングリコールモノイソプロピルエーテル、ジエチレングリコールモノブチルエーテル、ジエチレングリコールモノイソブチルエーテル、ジエチレングリコールモノヘキシルエーテルのジエチレングリコールモノアルキルエーテル類、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノプロピルエーテル、ジプロピレングリコールモノイソプロピルエーテル、ジプロピレングリコールモノブチルエーテル、ジプロピレングリコールモノイソブチルエーテル、ジプロピレングリコールモノヘキシルエーテル等のジプロピレングリコールモノアルキルエーテル類等のジアルキレングリコールモノアルキルエーテル類;
ジエチレングリコールモノフェニルエーテル等のジエチレングリコールモノアリールエーテル類、ジプロピレングリコールモノフェニルエーテル等のジプロピレングリコールモノアリールエーテル類等のジアルキレングリコールモノアリールエーテル類;
ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、ジエチレングリコールジプロピルエーテル、ジエチレングリコールジイソプロピルエーテル、ジエチレングリコールジブチルエーテル等のジエチレングリコールジアルキルエーテル類、ジプロピレングリコールジメチルエーテル、ジプロピレングリコールジエチルエーテル、ジプロピレングリコールジプロピルエーテル、ジプロピレングリコールジイソプロピルエーテル、ジプロピレングリコールジブチルエーテル等のジプロピレングリコールジアルキルエーテル類等のジアルキレングリコールジアルキルエーテル類;
ジエチレングリコールモノメチルエーテルアセテート、ジエチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノプロピルエーテルアセテート、ジエチレングリコールモノイソプロピルエーテルアセテート、ジエチレングリコールモノブチルエーテルアセテート、ジエチレングリコールモノイソブチルエーテルアセテート、ジエチレングリコールモノヘキシルエーテルアセテートのジエチレングリコールモノアルキルエーテルアセテート類、ジプロピレングリコールモノメチルエーテルアセテート、ジプロピレングリコールモノエチルエーテルアセテート、ジプロピレングリコールモノプロピルエーテルアセテート、ジプロピレングリコールモノイソプロピルエーテルアセテート、ジプロピレングリコールモノブチルエーテルアセテート、ジプロピレングリコールモノイソブチルエーテルアセテート、ジプロピレングリコールモノヘキシルエーテルアセテート等のジプロピレングリコールモノアルキルエーテルアセテート類等のジアルキレングリコールモノアルキルエーテルアセテート類;
トリエチレングリコールモノメチルエーテル、トリエチレングリコールモノエチルエーテル等のトリエチレングリコールモノアルキルエーテル類、トリプロピレングリコールモノメチルエーテル、トリプロピレングリコールモノエチルエーテル等のトリプロピレングリコールモノアルキルエーテル類等のトリアルキレングリコールモノアルキルエーテル類;
トリエチレングリコールジメチルエーテル、トリエチレングリコールジエチルエーテル等のトリエチレングリコールジアルキルエーテル類、トリプロピレングリコールジメチルエーテル、トリプロピレングリコールジエチルエーテル等のトリプロピレングリコールジアルキルエーテル類等のトリアルキレングリコールジアルキルエーテル類;
1−プロパノール、2−プロパノール、1−ブタノール、2−ブタノール、1−ペンタノール、1−ヘキサノール、1−ヘプタノール、1−ノナノール、1−デカノール、1−ウンデカノール、1−ドデカノール、1−テトラデカノール等の直鎖脂肪族アルコール類、シクロヘキサノール、2−メチルシクロヘキサノール等の環状脂肪族アルコール類等の脂肪族アルコール類;
フェノール等のフェノール類;
ベンジルアルコール等の芳香族アルコール類;
フルフリルアルコール等の複素環含有アルコール類;
テトラヒドロフルフリルアルコール等の水素化複素環含有アルコール類;
ジイソプロピルエーテル、ジ−n−ブチルエーテル、ジ−n−ヘキシルエーテル等のジアルキルエーテル類;
メチルフェニルエーテル、エチルフェニルエーテル、n−ブチルフェニルエーテル、ベンジル(3−メチルブチル)エーテル、(2−メチルフェニル)メチルエーテル、(3−メチルフェニル)メチルエーテル、(4−メチルフェニル)メチルエーテル等のアルキルアリールエーテル類;
エチルベンジルエーテル等のアルキルアラルキルエーテル類;
2−メチルフラン、テトラヒドロフラン、テトラヒドロピラン等の環状アルキルモノエーテル類;
1,4−ジオキサン等の環状アルキルジエーテル類;
トリオキサン等の環状アルキルトリエーテル類;
ジグリシジルエーテル等のジエポキシアルキルエーテル類;
エチルアセテート、n−プロピルアセテート、イソプロピルアセテート、n−ブチルアセテート、イソブチルアセテート、s−ブチルアセテート、t−ブチルアセテート、n−ペンチルアセテート、(3−メチルブチル)アセテート、n−ヘキシルアセテート、(2−エチルブチル)アセテート、(2−エチルヘキシル)アセテート等の直鎖状又は分岐状アルキルアセテート類、シクロヘキシルアセテート、2−メチルシクロヘキシルアセテート等の環状アルキルアセテート類等のアルキルアセテート類;エチルプロピオネート、n−プロピルプロピオネート、イソプロピルプロピオネート、n−ブチルプロピオネート、イソブチルプロピオネート、s−ブチルプロピオネート、t−ブチルプロピオネート、n−ペンチルプロピオネート、(3−メチルブチル)プロピオネート、n−ヘキシルプロピオネート、(2−エチルブチル)プロピオネート、(2−エチルヘキシル)プロピオネート等の直鎖状又は分岐状アルキルプロピオネート類、シクロヘキシルプロピオネート、2−メチルシクロヘキシルプロピオネート等の環状アルキルプロピオネート類等のアルキルプロピオネート類;エチルブチレート、n−プロピルブチレート、イソプロピルブチレート、n−ブチルブチレート、イソブチルブチレート、s−ブチルブチレート、t−ブチルブチレート、n−ペンチルブチレート、(3−メチルブチル)ブチレート、n−ヘキシルブチレート、(2−エチルブチル)ブチレート、(2−エチルヘキシル)ブチレート等の直鎖状又は分岐状アルキルブチレート類、シクロヘキシルブチレート、2−メチルシクロヘキシルブチレート等の環状アルキルブチレート類等のアルキルブチレート類;エチルラクテート、n−プロピルラクテート、イソプロピルラクテート、n−ブチルラクテート、イソブチルラクテート、s−ブチルラクテート、t−ブチルラクテート、n−ペンチルラクテート、(3−メチルブチル)ラクテート、n−ヘキシルラクテート、(2−エチルブチル)ラクテート、(2−エチルヘキシル)ラクテート等の直鎖状又は分岐状アルキルラクテート類、シクロヘキシルラクテート、2−メチルシクロヘキシルラクテート等の環状アルキルラクテート類等のアルキルラクテート類等のアルキルエステル類;
ベンジルアセテート等のアラルキルアセテート類、ベンジルプロピオネート等のアラルキルプロピオネート類、ベンジルブチレート等のアラルキルブチレート類、ベンジルラクテート等のアラルキルラクテート類等のアラルキルアルキルエステル類;
ジエチルケトン、ジイソブチルケトン、メチルエチルケトン、メチルn−プロピルケトン、メチルn−ブチルケトン、メチルイソブチルケトン、メチルn−プロピルケトン、メチルn−ヘキシルケトン、エチルn−ブチルケトン、ジ−n−プロピルケトン等のジアルキルケトン類;
イソホロン等の環状アルケニルケトン類;
シクロヘキサノン等の環状アルキルケトン類;
4−ヒドロキシ−4−メチル−2−ペンタノン(ジアセトンアルコール)等のヒドロキシジアルキルケトン類;
フルフラール等の複素環含有アルデヒド類;
ヘプタン、オクタン、2,2,3−トリメチルヘキサン、デカン、ドデカン等の直鎖状又は分岐状アルカン類;
トルエン、キシレン、o−キシレン、m−キシレン、p−キシレン、メシチレン、テトラリン、シクロヘキシルベンゼン等のアルキルベンゼン類;
シクロヘキサン、メチルシクロヘキサン、エチルシクロヘキサン等の環状アルカン類
等が挙げられるが、これらに限定されない。これらの溶媒は、1種又は2種以上使用することができる。
本発明の電荷輸送性ワニスは、前記アリールアミン誘導体からなる電荷輸送性物質、ドーパント及び有機溶媒を含むものである。
本発明の電荷輸送性ワニスは、塗布型電荷輸送薄膜形成用ワニスとして好適であり、当該ワニスを基材上に塗布して焼成することで、基材上に電荷輸送性薄膜を形成させることができる。
本発明の有機EL素子は、一対の電極を有し、これら電極の間に、前述の本発明の電荷輸送性薄膜を有するものである。
(a)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
(b)陽極/正孔注入層/正孔輸送層/発光層/電子注入輸送層/陰極
(c)陽極/正孔注入輸送層/発光層/電子輸送層/電子注入層/陰極
(d)陽極/正孔注入輸送層/発光層/電子注入輸送層/陰極
(e)陽極/正孔注入層/正孔輸送層/発光層/陰極
(f)陽極/正孔注入輸送層/発光層/陰極
(1)1H-NMR測定:日本電子(株)製、ECX-300
(2)ES-MS:Waters社製、ZQ2000
(3)MALDI-TOF MS:Bruker Daltonics社製、autoflex III smartbeam
(4)基板洗浄:長州産業(株)製、基板洗浄装置(減圧プラズマ方式)
(5)ワニスの塗布:ミカサ(株)製、スピンコーターMS-A100
(6)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
(7)有機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
(8)有機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
[合成例1]化合物H1の合成
特開2013−234169号公報に記載の方法に従い、下記式で表される化合物H1を合成した。
フラスコ内に、2−ブロモ−7−ヨードフルオレン7.42g、ジメチルスルホキシド30mL、ヨウ化カリウム330mg及び水酸化カリウム2.81gを入れた後、氷浴条件で攪拌しながらジエチレングリコール2−ブロモエチルメチルエーテルのジメチルスルホキシド混合液30mL(濃度:330g/L)を滴下した。1.5時間後、氷浴を外し室温で更に58.5時間攪拌した。反応混合物にイオン交換水及び酢酸エチルを加え、分液処理を行った。得られた有機層をイオン交換水、飽和食塩水で分液洗浄し、硫酸マグネシウムで乾燥した。溶媒を減圧留去した後、シリカゲルカラムクロマトグラフィー(展開溶媒:ヘキサン/酢酸エチル=40/60→0/100)により、分離、精製を行い、目的物を含むフラクションを集め、溶媒を減圧留去した後、乾燥を行い、下記式で表される中間体Aを得た(収量:8.16g、収率:62%)。1H-NMR及びES-MSの測定結果を以下に示す。
1H-NMR (300MHz, CDCl3 ) δ [ppm]: 7.74(d, J=1.4Hz, 1H), 7.67(dd, J=8.2,1.4Hz,1H), 7.44-7.54(m, 3H), 7.39(d, J=8.2Hz, 1H), 3.47-3.55(m, 8H), 3.37-3.41(m, 4H), 3.34(s, 6H), 3.19-3.22(m, 4H), 2.79(t, J=7.2Hz, 4H), 2.33(t, J=7.2Hz, 4H).
ES(+)-MS m/Z found: 680.19 ([M+NH4]+ calcd: 680.11).
フラスコ内に、中間体A4.97g、4−ビフェニルボロン酸1.49g、Pd(PPh3)4 175mg、トルエン35mL及び炭酸ナトリウム水溶液7mL(濃度:210g/L)を入れ、4時間還流攪拌した。放冷後、反応混合物にイオン交換水及び酢酸エチルを加え、分液処理を行った。得られた有機層をイオン交換水、飽和食塩水で分液洗浄し、硫酸マグネシウムで乾燥した。溶媒を減圧留去した後、シリカゲルカラムクロマトグラフィー(展開溶媒:ヘキサン/酢酸エチル=40/60→20/80)により、分離、精製を行い、目的物を含むフラクションを集め、溶媒を減圧留去した後、乾燥を行い、下記式で表される中間体Bを得た(収量:2.08g、収率:40%)。1H-NMR及びES-MSの測定結果を以下に示す。
1H-NMR(300MHz, CDCL3) δ [ppm]: 7.32-7.75(m, 15H), 3.42-3.51(m, 8H), 3.36-3.40(m, 4H), 3.30(s, 6H), 3.20-3.23(m, 4H), 2.82-2.88(m, 4H), 2.39-2.45(m, 4H).
ES(+)-MS m/Z found:706.46 ([M+NH4]+ calcd: 706.27).
フラスコ内に、中間体B2.08g、ビス(4−ビフェニリル)アミン1.06g、Pd(dba)2 51.8mg及びt−ブトキシナトリウム397mgを入れ、窒素置換をした後、トルエン15mL、あらかじめ調製しておいたトリ−t−ブチルホスフィンのトルエン溶液0.5mL(濃度:73g/L)を加え、80℃で2時間攪拌した。放冷後、反応混合物にイオン交換水及び酢酸エチルを加え、分液処理を行った。得られた有機層をイオン交換水、飽和食塩水で分液洗浄し、硫酸マグネシウムで乾燥した。溶媒を減圧留去した後、シリカゲルカラムクロマトグラフィー(展開溶媒:ヘキサン/酢酸エチル=70/30→0/100)により、分離、精製を行い、目的物を含むフラクションを集め、溶媒を減圧留去した後、乾燥を行い、下記式で表される化合物TEG−H1を得た(収量:2.19g、収率:78%)。1H-NMR及びMALDI-TOF MSの測定結果を以下に示す。
1H-NMR(300MHz, CDCl3) δ [ppm]: 7.14-7.76(m, 33H), 3.41-3.52(m, 12H), 3.25-3.35(m, 10H), 2.86-2.99(m, 4H), 2.26-2.43(m, 4H).
MALDI-TOF MS m/Z found: 929.07([m]+calcd: 929.47).
[実施例1−1]
化合物TEG−H1 0.052g及びリンタングステン酸(日本新金属(株)製)0.010gを、窒素雰囲気下でDMIB2gに溶解させて攪拌し、得られた溶液を孔径0.2μmのPTFE製フィルターを用いて濾過し、電荷輸送性ワニスを得た。
化合物H1 0.025g及びリンタングステン酸(日本新金属(株)製)0.005gを、窒素雰囲気下でDMIB2gに溶解させて攪拌し、得られた溶液を孔径0.2μmのPTFE製フィルターを用いて濾過し、電荷輸送性ワニスを得た。
化合物TEG−H1 0.062gを、窒素雰囲気下でDMIB2gに溶解させて攪拌し、得られた溶液を孔径0.2μmのPTFE製フィルターを用いて濾過し、電荷輸送性ワニスを得た。
[実施例2−1]
実施例1−1で得たワニスを、スピンコーターを用いてITO基板に塗布した後、80℃で1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25nmの均一な薄膜(正孔注入層)を形成した。ITO基板としては、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去した。
その上に、蒸着装置(真空度1.0×10-5Pa)を用いてα−NPD30nmを積層した。この際の蒸着レートは、0.2nm/秒とした。次いで、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、フッ化リチウム及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20nm、0.5nm及び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かわりに実施例1−2で得たワニスを用いた以外は、実施例2−1と同様の方法で素子を得た。
実施例1−1で得られたワニスのかわりに比較例1で得たワニスを用いた以外は、実施例2−1と同様の方法で素子を得た。
Claims (8)
- 式(1)で表されるアリールアミン誘導体からなる電荷輸送性物質、ドーパント及び有機溶媒を含むことを特徴とする電荷輸送性ワニス。
Rは、互いに独立して、ハロゲン原子、ニトロ基、シアノ基、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、Z1で置換されていてもよい炭素数1〜20のアルコキシ基、Z1で置換されていてもよい炭素数2〜20のアルケニルオキシ基、又はZ1で置換されていてもよい炭素数2〜20のアルキニルオキシ基を表し;
Z1は、ハロゲン原子、ニトロ基、シアノ基、Z2で置換されていてもよい炭素数6〜20のアリール基、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、Z2で置換されていてもよい炭素数1〜20のアルコキシ基、Z2で置換されていてもよい炭素数2〜20のアルケニルオキシ基、Z2で置換されていてもよい炭素数2〜20のアルキニルオキシ基、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;
Z2は、ハロゲン原子、ニトロ基又はシアノ基を表し;
nは、互いに独立して、0〜5の整数であり、mは、互いに独立して、0〜4の整数であり、pは、互いに独立して、0〜3の整数である。] - R1及びR2が、ともに炭素数1〜20のアルキル基又はともに少なくとも1つのエーテル構造を含む炭素数2〜20のアルキル基である請求項1記載の電荷輸送性ワニス。
- n、m及びpが、全て0である請求項1又は2記載の電荷輸送性ワニス。
- 前記ドーパントがヘテロポリ酸である請求項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。
- 式(1')で表されるアリールアミン誘導体。
Rは、互いに独立して、ハロゲン原子、ニトロ基、シアノ基、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、Z1で置換されていてもよい炭素数1〜20のアルコキシ基、Z1で置換されていてもよい炭素数2〜20のアルケニルオキシ基、又はZ1で置換されていてもよい炭素数2〜20のアルキニルオキシ基を表し;
Z1は、ハロゲン原子、ニトロ基、シアノ基、Z2で置換されていてもよい炭素数6〜20のアリール基、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、Z2で置換されていてもよい炭素数1〜20のアルコキシ基、Z2で置換されていてもよい炭素数2〜20のアルケニルオキシ基、Z2で置換されていてもよい炭素数2〜20のアルキニルオキシ基、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;
Z2は、ハロゲン原子、ニトロ基又はシアノ基を表し;
nは、互いに独立して、0〜5の整数であり、mは、互いに独立して、0〜4の整数であり、pは、互いに独立して、0〜3の整数である。]
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WO2008032616A1 (en) | 2006-09-13 | 2008-03-20 | Nissan Chemical Industries, Ltd. | Oligoaniline compounds |
CN101679206B (zh) | 2007-04-12 | 2016-05-11 | 日产化学工业株式会社 | 低聚苯胺化合物 |
CN102219700A (zh) * | 2011-04-22 | 2011-10-19 | 南京邮电大学 | 一种基于芴苯胺结构的有机光电材料 |
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JP2017135127A (ja) * | 2014-04-21 | 2017-08-03 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
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EP3249710B1 (en) | 2019-11-13 |
EP3249710A1 (en) | 2017-11-29 |
KR20170106397A (ko) | 2017-09-20 |
CN107210378A (zh) | 2017-09-26 |
TW201641486A (zh) | 2016-12-01 |
TWI680116B (zh) | 2019-12-21 |
EP3249710A4 (en) | 2018-10-03 |
WO2016117522A1 (ja) | 2016-07-28 |
JP6658549B2 (ja) | 2020-03-04 |
CN107210378B (zh) | 2019-11-26 |
KR102543975B1 (ko) | 2023-06-15 |
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