JPWO2016013556A1 - 電荷輸送性材料 - Google Patents
電荷輸送性材料 Download PDFInfo
- Publication number
- JPWO2016013556A1 JPWO2016013556A1 JP2016535942A JP2016535942A JPWO2016013556A1 JP WO2016013556 A1 JPWO2016013556 A1 JP WO2016013556A1 JP 2016535942 A JP2016535942 A JP 2016535942A JP 2016535942 A JP2016535942 A JP 2016535942A JP WO2016013556 A1 JPWO2016013556 A1 JP WO2016013556A1
- Authority
- JP
- Japan
- Prior art keywords
- charge transporting
- bis
- charge
- thin film
- halotetracyanoquinodimethane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims abstract description 85
- 239000010409 thin film Substances 0.000 claims abstract description 57
- -1 amide compound Chemical class 0.000 claims abstract description 36
- 239000000126 substance Substances 0.000 claims abstract description 34
- 239000008139 complexing agent Substances 0.000 claims abstract description 30
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 48
- 239000000758 substrate Substances 0.000 claims description 25
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical group FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 11
- 239000011964 heteropoly acid Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 230000000536 complexating effect Effects 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 238000005401 electroluminescence Methods 0.000 claims description 3
- 238000002347 injection Methods 0.000 abstract description 20
- 239000007924 injection Substances 0.000 abstract description 20
- 239000010410 layer Substances 0.000 description 48
- 229910052741 iridium Inorganic materials 0.000 description 38
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 28
- 239000002966 varnish Substances 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- 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 17
- 239000002019 doping agent Substances 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 13
- 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 13
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 238000000576 coating method Methods 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- 230000008569 process Effects 0.000 description 9
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 238000007789 sealing Methods 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 5
- 230000009918 complex formation Effects 0.000 description 5
- 238000010304 firing Methods 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 239000002861 polymer material Substances 0.000 description 5
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 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 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000002356 single layer Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- HASCQPSFPAKVEK-UHFFFAOYSA-N dimethyl(phenyl)phosphine Chemical compound CP(C)C1=CC=CC=C1 HASCQPSFPAKVEK-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- 229910052762 osmium Inorganic materials 0.000 description 3
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- 239000010937 tungsten Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 2
- 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 2
- XNCMQRWVMWLODV-UHFFFAOYSA-N 1-phenylbenzimidazole Chemical compound C1=NC2=CC=CC=C2N1C1=CC=CC=C1 XNCMQRWVMWLODV-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- QIYSYNQRYMNDQI-UHFFFAOYSA-N 5-methyl-1-phenylcyclohexa-2,4-diene-1-carboxamide Chemical compound C1(=CC=CC=C1)C1(C(=O)N)CC(=CC=C1)C QIYSYNQRYMNDQI-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- UHMVYRVEAXSAEB-UHFFFAOYSA-K [Ir+3].FC(C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-])(F)F.FC(F)(F)C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-].FC(F)(F)C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-] Chemical compound [Ir+3].FC(C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-])(F)F.FC(F)(F)C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-].FC(F)(F)C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-] UHMVYRVEAXSAEB-UHFFFAOYSA-K 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
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- 239000012535 impurity Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- YERGTYJYQCLVDM-UHFFFAOYSA-N iridium(3+);2-(4-methylphenyl)pyridine Chemical compound [Ir+3].C1=CC(C)=CC=C1C1=CC=CC=N1.C1=CC(C)=CC=C1C1=CC=CC=N1.C1=CC(C)=CC=C1C1=CC=CC=N1 YERGTYJYQCLVDM-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
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- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
- MQZFZDIZKWNWFX-UHFFFAOYSA-N osmium(2+) Chemical compound [Os+2] MQZFZDIZKWNWFX-UHFFFAOYSA-N 0.000 description 2
- 150000002926 oxygen Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
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- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
- 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 2
- 150000003577 thiophenes Chemical class 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 238000010023 transfer printing Methods 0.000 description 2
- 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 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 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 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- JXPQTGNDMKOBAT-UHFFFAOYSA-K (2-benzylphenyl)-phenylphosphinate iridium(3+) 5-pyridin-2-yl-3-(trifluoromethyl)pyrazole-3-carboxylate Chemical compound [Ir+3].C(C1=CC=CC=C1)C1=C(C=CC=C1)P([O-])(=O)C1=CC=CC=C1.FC(C1(N=NC(=C1)C1=NC=CC=C1)C(=O)[O-])(F)F.FC(C1(N=NC(=C1)C1=NC=CC=C1)C(=O)[O-])(F)F JXPQTGNDMKOBAT-UHFFFAOYSA-K 0.000 description 1
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N (2-methylphenyl)methanol Chemical compound CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 1
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- 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
- 238000000926 separation method Methods 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
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-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
- 238000003860 storage Methods 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
- 238000001308 synthesis method Methods 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
- 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
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- GBSZYMVOJYAZPH-UHFFFAOYSA-N thieno[2,3-e][1]benzothiole Chemical class S1C=CC2=C1C=CC1=C2SC=C1 GBSZYMVOJYAZPH-UHFFFAOYSA-N 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical class S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- KIGXXTRUJYDDKP-UHFFFAOYSA-N triphenyl-[4-[4-(4-triphenylsilylphenyl)phenyl]phenyl]silane Chemical group C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 KIGXXTRUJYDDKP-UHFFFAOYSA-N 0.000 description 1
- RFDGVZHLJCKEPT-UHFFFAOYSA-N tris(2,4,6-trimethyl-3-pyridin-3-ylphenyl)borane Chemical compound CC1=C(B(C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C(C)=CC(C)=C1C1=CC=CN=C1 RFDGVZHLJCKEPT-UHFFFAOYSA-N 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 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
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Abstract
Description
正孔注入層の形成方法は、蒸着法に代表されるドライプロセスと、スピンコート法に代表されるウェットプロセスとに大別され、これら各プロセスを比べると、ウェットプロセスの方が大面積に平坦性の高い薄膜を効率的に製造できる。それゆえ、有機ELディスプレイの大面積化が進められている現在、ウェットプロセスで形成可能な正孔注入層が望まれている。
このような事情に鑑み、本発明者らは、各種ウェットプロセスに適用可能であるとともに、有機EL素子の正孔注入層に適用した場合に優れたEL素子特性を実現できる薄膜を与える電荷輸送性材料や、それに用いる有機溶媒に対する溶解性の良好な化合物を開発してきている(例えば特許文献1〜4参照)。
しかし、正孔注入層用のウェットプロセス材料に関しては常に改善が求められており、特に、電荷輸送性に優れた薄膜を与えるウェットプロセス材料が求められている。
1. 電荷輸送性物質と、ハロテトラシアノキノジメタンと、このハロテトラシアノキノジメタンとの錯形成能を有する錯化剤とを含み、前記ハロテトラシアノキノジメタンと錯化剤とが錯形成していることを特徴とする電荷輸送性材料、
2. 前記錯化剤が、アミド化合物である1の電荷輸送性材料、
3. 前記アミド化合物が、1,3−ジメチル−2−イミダゾリジノンである2の電荷輸送性材料、
4. 前記ハロテトラシアノキノジメタンが、2,3,5,6−テトラフルオロ−7,7,8,8−テトラシアノキノジメタンである1〜3のいずれかの電荷輸送性材料、
5. さらにヘテロポリ酸を含む1〜4のいずれかの電荷輸送性材料、
6. 前記電荷輸送性物質が、電荷輸送性オリゴマーである1〜5のいずれかの電荷輸送性材料、
7. 1〜6のいずれかの電荷輸送性材料を用いて作製される電荷輸送性薄膜、
8. 7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、
9. 1〜6のいずれかの電荷輸送性材料を基材上に塗布し、乾燥させることを特徴とする電荷輸送性薄膜の製造方法、
10. 電荷輸送性物質と、ハロテトラシアノキノジメタンとを含む組成物から形成される電荷輸送性薄膜の電荷輸送性向上方法であって、前記組成物に前記ハロテトラシアノキノジメタンとの錯形成能を有する錯化剤を添加することを特徴とする電荷輸送性薄膜の電荷輸送性向上方法、
11. 電荷輸送性物質と、ハロテトラシアノキノジメタンと、有機溶媒とを含む組成物から形成される電荷輸送性薄膜の電荷輸送性向上方法であって、前記有機溶媒の少なくとも一部として、前記ハロテトラシアノキノジメタンとの錯形成能を有する錯化剤を用いることを特徴とする電荷輸送性薄膜の電荷輸送性向上方法、
12. 前記錯化剤が、アミド化合物である10または11の電荷輸送性向上方法、
13. アミド化合物からなるハロテトラシアノキノジメタンの錯化剤、
14. アミド化合物からなる、電荷輸送性物質およびハロテトラシアノキノジメタンを含む電荷輸送性薄膜の電荷輸送性向上剤
を提供する。
また、電荷輸送性材料中でハロテトラシアノキノジメタンが錯化剤と錯形成しているため、材料の保存安定性が向上するという利点も有する。
本発明の電荷輸送性材料から作製した薄膜は、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、低駆動電圧の有機EL素子を得ることができる。
また、本発明の電荷輸送性材料は、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。
本発明に係る電荷輸送性材料は、電荷輸送性物質と、ハロテトラシアノキノジメタンと、このハロテトラシアノキノジメタンとの錯形成能を有する錯化剤とを含み、ハロテトラシアノキノジメタンと錯化剤とが錯形成しているものである。
電荷輸送性化合物の具体例としては、オリゴアニリン誘導体、N,N'−ジアリールベンジジン誘導体、N,N,N',N'−テトラアリールベンジジン誘導体等のアリールアミン誘導体、オリゴチオフェン誘導体、チエノチオフェン誘導体、チエノベンゾチオフェン誘導体等のチオフェン誘導体、オリゴピロール誘導体等のピロール誘導体等の各種正孔輸送性物質が挙げられるが、中でも、アリールアミン誘導体、チオフェン誘導体が好ましく、アリールアミン誘導体がより好ましい。
なお、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、ドーパント物質とともに用いた際に電荷輸送性が発揮されるものでもよい。
また、薄膜化した場合に電荷輸送性物質が分離することを防ぐ観点から、電荷輸送性化合物は分子量分布のない(分散度が1)ことが好ましい(すなわち、単一の分子量であることが好ましい)。
ハロゲン原子としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子等が挙げられるが、フッ素原子または塩素原子が好ましく、フッ素原子がより好ましい。
その他のドーパント物質としては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。
特に、1種類のヘテロポリ酸を用いる場合、その1種類のヘテロポリ酸は、リンタングステン酸またはリンモリブデン酸が好ましく、リンタングステン酸が最適である。また、2種類以上のヘテロポリ酸を用いる場合、その2種類以上のヘテロポリ酸の1つは、リンタングステン酸またはリンモリブデン酸が好ましく、リンタングステン酸がより好ましい。
なお、ヘテロポリ酸は、元素分析等の定量分析において、一般式で示される構造から元素の数が多いもの、または少ないものであっても、それが市販品として入手したもの、あるいは、公知の合成方法にしたがって適切に合成したものである限り、本発明において用いることができる。
すなわち、例えば、一般的には、リンタングステン酸は化学式H3(PW12O40)・nH2Oで、リンモリブデン酸は化学式H3(PMo12O40)・nH2Oでそれぞれ示されるが、定量分析において、この式中のP(リン)、O(酸素)またはW(タングステン)もしくはMo(モリブデン)の数が多いもの、または少ないものであっても、それが市販品として入手したもの、あるいは、公知の合成方法にしたがって適切に合成したものである限り、本発明において用いることができる。この場合、本発明に規定されるヘテロポリ酸の質量とは、合成物や市販品中における純粋なリンタングステン酸の質量(リンタングステン酸含量)ではなく、市販品として入手可能な形態および公知の合成法にて単離可能な形態において、水和水やその他の不純物等を含んだ状態での全質量を意味する。
ベンゾキノン誘導体の具体例としては、テトラクロロ−1,4−ベンゾキノン(クロラニル)、2,3−ジクロロ−5,6−ジシアノ−1,4−ベンゾキノン(DDQ)などが挙げられる。
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。
アミド化合物の具体例としては、1,3−ジメチル−2−イミダゾリジノン、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,N−ジメチルアセトアミド、N−メチルピロリドン等の常温で液状の炭素数3〜5のアミド化合物が挙げられるが、中でも、1,3−ジメチル−2−イミダゾリジノンが好ましい。
なお、このような炭素数3〜5のアミド化合物は、電荷輸送性物質(特に分子量200〜9,000の電荷輸送性化合物)およびハロテトラシアノキノジメタン化合物を良好に溶解するため、錯化剤および溶液(ワニス)の態様である本発明の電荷輸送性材料の溶媒として機能し得る。それゆえ、当該アミド化合物を用いることで、平坦性に優れる薄膜を与えるワニスとして、本発明の電荷輸送性材料を得ることができる。
このような高溶解性溶媒としては、例えば、シクロヘキサノン、ジエチレングリコールモノメチルエーテル等の有機溶媒が挙げられる。これらの溶媒は1種単独で、または2種以上混合して用いることができ、その使用量は、溶媒全体に対して1〜90質量%の範囲内で、錯形成の阻害の程度、電荷輸送性物質等の溶解性の程度等を考慮しながら適宜決定される。
なお、ここで言う「溶媒全体」の「溶媒」とは、錯化剤が溶媒として機能する場合は当該錯化剤全ておよびその他の溶媒全ての合算を意味し、錯化剤が溶媒として機能しない場合はその他の溶媒全ての合算を意味する(以下、同様)。
高粘度有機溶媒としては、例えば、シクロヘキサノール、エチレングリコール、エチレングリコールジクリシジルエーテル、1,3−オクチレングリコール、ジエチレングリコール、ジプロピレングリコール、トリエチレングリコール、トリプロピレングリコール、1,3−ブタンジオール、2,3−ブタンジオール、1,4−ブタンジオール、プロピレングリコール、へキシレングリコール等が挙げられる。これらの溶媒は単独で用いてもよく、2種以上混合して用いてもよい。
高粘度有機溶媒の添加割合は、溶媒全体に対して1〜90質量%の範囲内で、錯形成の阻害の程度、電荷輸送性物質等の溶解性の程度等を考慮しながら適宜決定される。
これらの溶媒は1種単独で、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材料の固形分濃度は、電荷輸送性材料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、電荷輸送性材料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。
そ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、スリットコート法、転写印刷法、ロールコート法、刷毛塗り、インクジェット法、スプレー法等が挙げられ、塗布方法に応じて電荷輸送性材料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。
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、陽極基板上に本発明の電荷輸送性材料を塗布して焼成し、電極上に正孔注入層を作製する。これを真空蒸着装置内に導入し、正孔輸送層、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。
上記OLED素子作製において、正孔輸送層、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、正孔輸送性高分子層、発光性高分子層を順次形成することによって本発明の電荷輸送性材料によって形成される電荷輸送性薄膜を有するPLED素子を作製することができる。
具体的には、陽極基板上に本発明の電荷輸送性材料を塗布して上記の方法により正孔注入層を作製し、その上に正孔輸送性高分子層、発光性高分子層を順次形成し、さらに陰極電極を蒸着してPLED素子とする。
正孔輸送性高分子層および発光性高分子層の形成法としては、正孔輸送性高分子材料もしくは発光性高分子材料、またはこれら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、正孔注入層または正孔輸送性高分子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。
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)1H−NMR:日本電子(株)製 JNM−ECP300 FT NMR SYSTEM
(2)ワニスのUV−Visスペクトル測定:(株)島津製作所製 可視紫外線吸収スペクトル測定装置UV−3100PC
(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
1H-NMR(300MHz, DMSO-d6) δ[ppm]:8.10(d, J=7.8Hz, 2H), 7.99(d, J=1.8Hz, 2H), 7.59-7.66(m, 4H), 7.42-7.51(m, 6H), 7.23-7.29(m, 7H), 6.94-7.18(m, 11H).
[実施例1−1]
AN1 0.143g、リンタングステン酸(PTA)0.416gおよびF4TCNQ0.273gを、窒素雰囲気下で、錯化剤である1,3−ジメチル−2−イミダゾリジノン(DMI)14.0gに溶解させた。得られた溶液に、2,3−ブタンジオール(2,3−BD)4.0gおよびジプロピレングリコールモノメチルエーテル(DPM)2.0gを加えて撹拌し、電荷輸送性材料(ワニス)を調製した。
AN1 0.143g、PTA0.416gおよびF4TCNQ0.273gを、窒素雰囲気下で、シクロヘキサノン(CHN)20gに溶解させ、得られた溶液を撹拌し、電荷輸送性材料(ワニス)を調製した。
実施例1−1および比較例1−1で調製したワニスを、それぞれ質量基準で1,000倍に希釈した。なお、実施例1−1のワニスの希釈には、混合溶媒(DMI:2,3−BD:DPM=70:20:10)を、比較例1−1のワニスの希釈にはシクロヘキサノンを、それぞれ用いた。そして、各希釈したワニスのUV−Visスペクトル(波長300〜1,000nm、以下同様)を測定した。結果を図1に示す。
F4TCNQ0.068gを、窒素雰囲気下で、DMI3.5gに溶解させた。得られた溶液に、2,3−BD1.0gおよびDPM0.5gを加えて撹拌し、溶液A1を調製した。
(2)溶液A2
PTA0.104gを、窒素雰囲気下で、DMI3.5gに溶解させた。得られた溶液に、2,3−BD1.0gおよびDPM0.5gを加えて撹拌し、溶液A2を調製した。
(3)溶液A3
AN1 0.143gを、窒素雰囲気下で、DMI3.5gに溶解させた。得られた溶液に、2,3−BD1.0gおよびDPM0.5gを加えて撹拌し、溶液A3を調製した。
(4)溶液A4
F4TCNQ0.068gを、窒素雰囲気下で、DMI5gを加えて溶解させ、得られた溶液を撹拌し、溶液A4を調製した。
一方、図1に示されるように、比較例1−1のワニスは、波長600〜1,000nmに上述のような吸収を有していなかった。
また、図2に示されるように、F4TCNQを添加せずにリンタングステン酸のみやアリールアミン誘導体(AN1)のみを混合溶媒に溶解させて調製した溶液も波長600〜1,000nmに上述のような吸収を有していなかった。
これらの事実は、ワニス中でF4TCNQとDMIが相互作用し、ある種の錯体を形成していることを示唆している。
なお、実施例1−1のワニスの600〜1,000nmにかけての吸収では、2つの顕著なピークが認められる(750〜800nmの間および850〜900nmの間)。それぞれピークの波長は、762nm、866nmであった。
電気特性を評価する際の基板には、インジウム錫酸化物が表面上に膜厚150nmでパターニングされた25mm×25mm×0.7tのガラス基板(以下、ITO基板と略す)を用いた。ITO基板は、O2プラズマ洗浄装置(150W、30秒間)を用いて表面上の不純物を除去してから使用した。
実施例1−1で得られたワニスを、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、さらに、大気雰囲気下、230℃で15分間焼成し、ITO基板上に30nmの均一な薄膜を形成した。
次いで、薄膜を形成したITO基板に対し、蒸着装置を用いてアルミニウム薄膜を形成して単層素子を得た。アルミニウム薄膜の膜厚は120nmとし、蒸着は、真空度1.3×10-3Pa、蒸着レート0.2nm/秒の条件で行った。
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、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、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、比較例1−1で得られたワニスを用いた以外は、実施例2−1と同様の方法で単層素子を作製した。
[実施例3−1]
実施例1−1で得られたワニスを用い、実施例2−1と同様の方法で、ITO基板上に30nmの均一な薄膜を形成した。
次いで、薄膜を形成したITO基板に対し、蒸着装置(真空度1.0×10-5Pa)を用いてN,N'−ジ(1−ナフチル)−N,N'−ジフェニルベンジジン(α−NPD)、トリス(8−キノリノラート)アルミニウム(III)(Alq3)、フッ化リチウム、およびアルミニウムの薄膜を順次積層し、有機EL素子を得た。この際、蒸着レートは、α−NPD、Alq3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30nm、40nm、0.5nmおよび100nmとした。
そして、実施例2−1と同様の方法で、有機EL素子は封止基板により封止した。
実施例1−1で得られたワニスの代わりに、比較例1−1で得られたワニスを用いた以外は、実施例3−1と同様の方法で有機EL素子を作製した。
以上のとおり、本発明の電荷輸送性材料から得られる薄膜を有機EL素子の正孔注入層として用いることで、有機EL素子の低駆動電圧化が可能となる。
Claims (14)
- 電荷輸送性物質と、ハロテトラシアノキノジメタンと、このハロテトラシアノキノジメタンとの錯形成能を有する錯化剤とを含み、
前記ハロテトラシアノキノジメタンと錯化剤とが錯形成していることを特徴とする電荷輸送性材料。 - 前記錯化剤が、アミド化合物である請求項1記載の電荷輸送性材料。
- 前記アミド化合物が、1,3−ジメチル−2−イミダゾリジノンである請求項2記載の電荷輸送性材料。
- 前記ハロテトラシアノキノジメタンが、2,3,5,6−テトラフルオロ−7,7,8,8−テトラシアノキノジメタンである請求項1〜3のいずれか1項記載の電荷輸送性材料。
- さらにヘテロポリ酸を含む請求項1〜4のいずれか1項記載の電荷輸送性材料。
- 前記電荷輸送性物質が、電荷輸送性オリゴマーである請求項1〜5のいずれか1項記載の電荷輸送性材料。
- 請求項1〜6のいずれか1項記載の電荷輸送性材料を用いて作製される電荷輸送性薄膜。
- 請求項7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。
- 請求項1〜6のいずれか1項記載の電荷輸送性材料を基材上に塗布し、乾燥させることを特徴とする電荷輸送性薄膜の製造方法。
- 電荷輸送性物質と、ハロテトラシアノキノジメタンとを含む組成物から形成される電荷輸送性薄膜の電荷輸送性向上方法であって、前記組成物に前記ハロテトラシアノキノジメタンとの錯形成能を有する錯化剤を添加することを特徴とする電荷輸送性薄膜の電荷輸送性向上方法。
- 電荷輸送性物質と、ハロテトラシアノキノジメタンと、有機溶媒とを含む組成物から形成される電荷輸送性薄膜の電荷輸送性向上方法であって、
前記有機溶媒の少なくとも一部として、前記ハロテトラシアノキノジメタンとの錯形成能を有する錯化剤を用いることを特徴とする電荷輸送性薄膜の電荷輸送性向上方法。 - 前記錯化剤が、アミド化合物である請求項10または11記載の電荷輸送性向上方法。
- アミド化合物からなるハロテトラシアノキノジメタンの錯化剤。
- アミド化合物からなる、電荷輸送性物質およびハロテトラシアノキノジメタンを含む電荷輸送性薄膜の電荷輸送性向上剤。
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EP3174116B1 (en) | 2020-09-23 |
EP3174116A4 (en) | 2018-01-17 |
KR20220100088A (ko) | 2022-07-14 |
US20170213981A1 (en) | 2017-07-27 |
KR102586572B1 (ko) | 2023-10-10 |
EP3174116A1 (en) | 2017-05-31 |
CN106663741B (zh) | 2019-06-28 |
TWI674253B (zh) | 2019-10-11 |
US10141517B2 (en) | 2018-11-27 |
CN106663741A (zh) | 2017-05-10 |
TW201619127A (zh) | 2016-06-01 |
KR20170035994A (ko) | 2017-03-31 |
WO2016013556A1 (ja) | 2016-01-28 |
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