JP5806336B2 - 電気活性組成物 - Google Patents
電気活性組成物 Download PDFInfo
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- JP5806336B2 JP5806336B2 JP2013554543A JP2013554543A JP5806336B2 JP 5806336 B2 JP5806336 B2 JP 5806336B2 JP 2013554543 A JP2013554543 A JP 2013554543A JP 2013554543 A JP2013554543 A JP 2013554543A JP 5806336 B2 JP5806336 B2 JP 5806336B2
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- 239000000203 mixture Substances 0.000 title claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 59
- 239000002019 doping agent Substances 0.000 claims description 35
- -1 phenylnaphthyl Chemical group 0.000 claims description 25
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 239000000654 additive Substances 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 10
- 230000000996 additive effect Effects 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 3
- 239000010410 layer Substances 0.000 description 115
- 239000000463 material Substances 0.000 description 77
- 150000001875 compounds Chemical class 0.000 description 30
- 239000007788 liquid Substances 0.000 description 26
- 230000005525 hole transport Effects 0.000 description 24
- 238000002347 injection Methods 0.000 description 23
- 239000007924 injection Substances 0.000 description 23
- 229910052751 metal Inorganic materials 0.000 description 21
- 239000002184 metal Substances 0.000 description 21
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- 125000000217 alkyl group Chemical group 0.000 description 17
- 238000000151 deposition Methods 0.000 description 16
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 15
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 14
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- 238000004770 highest occupied molecular orbital Methods 0.000 description 13
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- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
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- 230000005264 electron capture Effects 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 9
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 7
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000005281 excited state Effects 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
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- 229920003026 Acene Polymers 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
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- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 238000004364 calculation method Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000007641 inkjet printing Methods 0.000 description 4
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- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000007764 slot die coating Methods 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 125000005580 triphenylene group Chemical group 0.000 description 4
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 3
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 238000003775 Density Functional Theory Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000002800 charge carrier Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
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- 238000003818 flash chromatography Methods 0.000 description 3
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
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- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 2
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- KAXFFNSOEBLXEE-UHFFFAOYSA-N 2,4-dichloro-6-(4-propan-2-ylphenyl)-1,3,5-triazine Chemical compound C1=CC(C(C)C)=CC=C1C1=NC(Cl)=NC(Cl)=N1 KAXFFNSOEBLXEE-UHFFFAOYSA-N 0.000 description 2
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 2
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical class C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 2
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- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 2
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- CFPMTYLOUSWLLM-UHFFFAOYSA-N 1-naphthalen-2-ylnaphthalene Chemical group C1=CC=C2C(C3=CC4=CC=CC=C4C=C3)=CC=CC2=C1 CFPMTYLOUSWLLM-UHFFFAOYSA-N 0.000 description 1
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- VMAUSAPAESMXAB-UHFFFAOYSA-N 2,3-bis(4-fluorophenyl)quinoxaline Chemical compound C1=CC(F)=CC=C1C1=NC2=CC=CC=C2N=C1C1=CC=C(F)C=C1 VMAUSAPAESMXAB-UHFFFAOYSA-N 0.000 description 1
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- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
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- 125000001072 heteroaryl group Chemical group 0.000 description 1
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 1
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- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
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- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
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- 229920000548 poly(silane) polymer Polymers 0.000 description 1
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- BUAWIRPPAOOHKD-UHFFFAOYSA-N pyrene-1,2-diamine Chemical compound C1=CC=C2C=CC3=C(N)C(N)=CC4=CC=C1C2=C43 BUAWIRPPAOOHKD-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
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- 239000002002 slurry Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JIIYLLUYRFRKMG-UHFFFAOYSA-N tetrathianaphthacene Chemical compound C1=CC=CC2=C3SSC(C4=CC=CC=C44)=C3C3=C4SSC3=C21 JIIYLLUYRFRKMG-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 239000010981 turquoise Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/30—Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/90—Multiple hosts in the emissive layer
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- Electroluminescent Light Sources (AREA)
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Description
本出願は、米国特許法第119条(e)に基づき、2011年2月14日に出願された米国仮特許出願第61/442398号明細書および2011年3月22日に出願された米国仮特許出願第61/466195号明細書の優先権を主張する。上記米国仮特許出願は両方とも記載内容全体が参照により本明細書に援用される。
Eは、それぞれ、同一であるか、または異なって、NまたはC−Ar1であるが、ただし、少なくとも1つのE=Nであり、そして
Ar1は、それぞれ、同一であるか、または異なって、H、Dまたはアリールであるが、ただし、少なくとも1つのAr1はアリールである)
を有する添加剤を含んでなる電気活性組成物が提供される。
以下に記載される実施形態の詳細を記載する前に、一部の用語について定義または説明を行う。
添加剤は、式I
Eは、それぞれ、同一であるか、または異なって、NまたはC−Ar1であるが、ただし、少なくとも1つのE=Nであり、そして
Ar1は、それぞれ、同一であるか、または異なって、H、Dまたはアリールであるが、ただし、少なくとも1つのAr1はアリールである)
を有する化合物である。
新規電気活性組成物は、(a)ホスト、(b)ドーパント、および(c)上記式Iを有する添加剤を含んでなる。いくつかの実施形態において、ホストは、電気活性組成物の全重量に基づき、50〜95重量%の範囲で存在し、ドーパントは、電気活性組成物の全重量に基づき、3〜10重量%の範囲で存在し、そして式Iを有する化合物は、電気活性組成物の全重量に基づき、0.001〜10重量%の範囲で存在する。
いくつかの実施形態において、ホストは重水素化される。いくつかの実施形態において、ホストは少なくとも10%重水素化され、いくつかの実施形態において、少なくとも20%重水素化され、いくつかの実施形態において、少なくとも30%重水素化され、いくつかの実施形態において、少なくとも40%重水素化され、いくつかの実施形態において、少なくとも50%重水素化され、いくつかの実施形態において、少なくとも60%重水素化され、いくつかの実施形態において、少なくとも70%重水素化され、いくつかの実施形態において、少なくとも80%重水素化され、いくつかの実施形態において、少なくとも90%重水素化される。いくつかの実施形態において、ホストは100%重水素化される。
Tは、(CR’)g、SiR2、S、SO2、PR、PO、PO2、BRおよびRからなる群から選択され、
Rは、それぞれ、同一であるか、または異なって、アルキル、アリール、シリルまたはそれらの重水素化類似物からなる群から選択され、
R’は、それぞれ、同一であるか、または異なって、H、D、アルキルおよびシリルからなる群から選択され、
gは1〜6の整数であり、そして
mは1〜6の整数である)
を有する。
発光性ドーパント材料には、小分子有機蛍光化合物、ルミネセント金属錯体およびそれらの混合物が含まれる。蛍光化合物の例には、限定されないが、ピレン、ペリレン、ルブレン、クマリン、それらの誘導体およびそれらの混合物が含まれる。金属錯体の例には、限定されないが、トリス(8−ヒドロキシキノラト)アルミニウム(AlQ)などの金属キレート化オキシノイド化合物、Petrovら、米国特許第6,670,645号明細書ならびに国際公開第03/063555号パンフレットおよび同第2004/016710号パンフレットに開示されるフェニルピリジン、フェニルキノリン、フェニルイソキノリンまたはフェニルピリミジン配位子とのイリジウムの錯体などのシクロメタレート化イリジウムおよび白金エレクトロルミネセント化合物、および、例えば、国際公開第03/008424号パンフレット、同第03/091688号パンフレットおよび同第03/040257号パンフレットに記載される有機金属化合物錯体、ならびにそれらの混合物が含まれる。
Aは、それぞれ、同一であるか、または異なって、3〜60個の炭素原子を有する芳香族基であり、
Qは、単結合または3〜60個の炭素原子を有する芳香族基であり、
nおよびmは、独立して、1〜6の整数である)から選択される。
添加剤は、上記で検討された通りである。
いくつかの実施形態において、2種のホストが存在する。いくつかの実施形態において、第1のホスト(a)は電子輸送より速い正孔輸送を促進し、正孔輸送ホストと呼ばれ、そして第2のホスト(d)は、正孔輸送より速い電子輸送を促進し、電子輸送ホストと呼ばれる。
本明細書に記載の電気活性材料を含んでなる1層またはそれ以上の層を有することから有益となり得る有機電子デバイスとしては、限定されないが、(1)電気エネルギーを放射線に変換するデバイス(例えば、発光ダイオード、発光ダイオードディスプレイ、照明デバイス、照明器具、またはダイオードレーザー)、(2)電子的プロセスを介して信号を検出するデバイス(例えば、光検出器、光導電セル、フォトレジスタ、光スイッチ、光トランジスタ、光電管、IR検出器、バイオセンサー)、(3)放射線を電気エネルギーに変換するデバイス(例えば、光起電力デバイスまたは太陽電池)、ならびに(4)1つまたはそれ以上の有機半導体層を含む1つまたはそれ以上の電子部品を含むデバイス(例えば、トランジスタまたはダイオード)が挙げられる。
いくつかの実施形態において、光活性層は、上記電気活性層を含んでなる。いくつかの実施形態において、光活性層は、(a)ホスト、(b)ドーパントおよび(c)式Iを有する添加剤から本質的になる。いくつかの実施形態において、光活性層は、(a)ホスト、(b)ドーパント、(c)式Iを有する添加剤、および(d)第2のホストから本質的になる。ドーパント対全ホスト材料の重量比は、5:95〜70:30、いくつかの実施形態においては90:10〜80:20の範囲にある。
デバイスの他の層は、そのような層で有用であることが知られている任意の材料から製造することができる。
デバイス層は、気相堆積、液相堆積および熱転写などの任意の堆積技術またはそれらの技術の組み合わせによって形成することができる。
本実施例は、化合物C1(4,4’−(6−(4−イソプロピルフェニル)−1,3,5−トリアジン−2,4−ジイル)ジベンゾニトリル)の調製を説明する。
ドライボックス中、3つ口250ml丸底フラスコに、塩化シアヌル酸(1.84g、10mmol)および無水THF(50ml)を装填した。1つ口50ml丸底フラスコに、MgBr2・OEt2(2.58g、10mmol)および無水THF(22ml)を装填した。4−イソ−プロピルブロモベンゼン(1.99g、10mmol)もドライボックス中で、100mlの3つ口丸底フラスコ中で20mlの無水THFに溶解した。全ての3つ口フラスコに栓をして、ドライボックスから取り出し、真空ラインに接続した。臭化アリール溶液を含むフラスコを−78Cまで冷却し、そしてn−ブチルリチウム(8ml、20mmol、ヘキサン中2.5M)の溶液をシリンジで滴下して添加した(シリンジロック使用)。添加の間、混合物の温度を−70℃未満に保持した。冷水浴を取り外し、そして溶液を室温まで加温した。これを室温で30分間攪拌し、次いで−15℃まで冷却した。二臭化マグネシウムスラリーをカニューレを通して迅速に添加したところ、透明な黄色溶液が得られた。塩化シアヌル酸溶液を0℃まで冷却し、滴下漏斗を備えた。グリニャール溶液をカニューレによって滴下漏斗に移し、温度を約−5℃に保持しながら、迅速に添加した。反応混合物を、攪拌しながら、室温まで一晩かけて徐々に加温した。混合物の色は、黄色からオレンジ色、暗赤色に変化した。次の日、クエン酸溶液(50ml、5重量%)の添加によって反応を停止させた。THFを減圧下で除去し、そして水性残渣をCH2Cl2(3×50ml)で抽出した。洗浄した有機相を組み合わせて、Na2SO4上で乾燥し、濃縮したところ、赤色液体が得られた。粗製生成物をフラッシュクロマトグラフィ(CH2Cl2/ヘキサン勾配)によってさらに精製したところ、0.45g(17%)の生成物が得られた。1H NMRおよびLC−MSは構造と一致した。
2,4−ジクロロ−6−(4−イソプロピルフェニル)−1,3,5−トリアジン(1.2g、4.48mmol)を、100ml丸底フラスコ中で、ジメトキシエタン(25ml)に溶解した。水(13ml)を添加し、そして窒素を15分間混合物に通してバブリングした。次に4−シアノフェニルボロン酸(1.56g、10.29mmol)を添加し、続いて、炭酸カリウム(3.71g、26.85mmol)を添加した。テトラキス(トリフェニルホスフィン)パラジウム(0.517g、0.45mmol、10モル%)を最後に添加した。フラスコに、窒素バブラーに接続された還流冷却器を取り付けた。反応混合物を加熱浴に配置し、一晩(19時間)還流させた。次の日、反応混合物を室温に冷却した。揮発性物質を減圧下で除去した。残留する水層を水およびCH2Cl2(それぞれ100ml)で抽出した。水層を分離し、追加のCH2Cl2(110ml)で洗浄した。有機層を組み合わせ、水(2×100ml)、食塩水(100ml)で洗浄し、MgSO4上で乾燥し、濃縮したところ、粗製生成物が得られた。フラッシュクロマトグラフィ(CH2Cl2/ヘキサン勾配)による精製によって、0.1g(5.5%)の生成物が得られた。LC/MSおよび1H NMRによって構造を確認した。
本実施例は、化合物C2(3,3’−(6−(4−イソプロピルフェニル)−1,3,5−トリアジン−2,4−ジイル)ジベンゾニトリル)の調製を説明する。
Claims (6)
- 前記光活性層が、
(d)第2のホスト
をさらに含む、請求項1に記載のデバイス。 - Ar1〜Ar3の少なくとも1つが、電子求引基を有するアリールである、請求項3に記載の組成物。
- 少なくとも1つのAr1が、フェニル、ビフェニル、ナフチル、ビナフチル、フェニルナフチル、ナフチルフェニル、カルバゾリルフェニル、ジアリールアミノフェニル、それらの置換された誘導体、およびそれらの重水素化類似物からなる群から選択される、請求項3に記載の組成物。
- Ar1が炭化水素アリールである、請求項3に記載の組成物。
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