JP2018524379A - 複素環式化合物、ならびに、電気光学デバイスまたは光電子デバイスにおける複素環式化合物の使用 - Google Patents
複素環式化合物、ならびに、電気光学デバイスまたは光電子デバイスにおける複素環式化合物の使用 Download PDFInfo
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- JP2018524379A JP2018524379A JP2018502225A JP2018502225A JP2018524379A JP 2018524379 A JP2018524379 A JP 2018524379A JP 2018502225 A JP2018502225 A JP 2018502225A JP 2018502225 A JP2018502225 A JP 2018502225A JP 2018524379 A JP2018524379 A JP 2018524379A
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- 230000005693 optoelectronics Effects 0.000 title description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 230000005525 hole transport Effects 0.000 claims abstract description 27
- -1 1-thianthenyl Chemical group 0.000 claims abstract description 16
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 claims description 30
- 238000002347 injection Methods 0.000 claims description 17
- 239000007924 injection Substances 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 17
- 239000002019 doping agent Substances 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
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- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000013086 organic photovoltaic Methods 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 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 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 239000010408 film Substances 0.000 claims description 2
- 238000003384 imaging method Methods 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 2
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 8
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 8
- 230000009477 glass transition Effects 0.000 abstract description 6
- 239000010410 layer Substances 0.000 description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 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 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
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- 239000012043 crude product Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 229910045601 alloy Inorganic materials 0.000 description 5
- 239000000956 alloy Substances 0.000 description 5
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000004054 semiconductor nanocrystal Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 3
- 229920000144 PEDOT:PSS Polymers 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
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- 239000000843 powder Substances 0.000 description 3
- 239000012264 purified product Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- WNEXSUAHKVAPFK-UHFFFAOYSA-N 2,8-dibromodibenzothiophene Chemical compound C1=C(Br)C=C2C3=CC(Br)=CC=C3SC2=C1 WNEXSUAHKVAPFK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- TWWQCBRELPOMER-UHFFFAOYSA-N [4-(n-phenylanilino)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 TWWQCBRELPOMER-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- VNZZUWADVGKWCN-UHFFFAOYSA-J quinoline-2-carboxylate zirconium(4+) Chemical compound [Zr+4].C1=CC=CC2=NC(C(=O)[O-])=CC=C21.C1=CC=CC2=NC(C(=O)[O-])=CC=C21.C1=CC=CC2=NC(C(=O)[O-])=CC=C21.C1=CC=CC2=NC(C(=O)[O-])=CC=C21 VNZZUWADVGKWCN-UHFFFAOYSA-J 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical group C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 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 1
- UPSWHSOSMRAWEH-UHFFFAOYSA-N 2-n,3-n,4-n-tris(3-methylphenyl)-1-n,1-n,2-n,3-n,4-n-pentakis-phenylbenzene-1,2,3,4-tetramine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=C(N(C=3C=CC=CC=3)C=3C=C(C)C=CC=3)C(N(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 UPSWHSOSMRAWEH-UHFFFAOYSA-N 0.000 description 1
- UDQLIWBWHVOIIF-UHFFFAOYSA-N 3-phenylbenzene-1,2-diamine Chemical compound NC1=CC=CC(C=2C=CC=CC=2)=C1N UDQLIWBWHVOIIF-UHFFFAOYSA-N 0.000 description 1
- KIGVOJUDEQXKII-UHFFFAOYSA-N 4-bromo-n-(4-bromophenyl)-n-phenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC(Br)=CC=1)C1=CC=CC=C1 KIGVOJUDEQXKII-UHFFFAOYSA-N 0.000 description 1
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 1
- CYQJVOFFLVMYOY-UHFFFAOYSA-N 4-phenothiazin-10-yl-N,N-diphenylaniline Chemical compound S1c2ccccc2N(c2ccc(cc2)N(c2ccccc2)c2ccccc2)c2ccccc12 CYQJVOFFLVMYOY-UHFFFAOYSA-N 0.000 description 1
- RRDTWBBIYVHARV-UHFFFAOYSA-N 9-(4-thianthren-1-ylphenyl)carbazole Chemical compound S1c2ccccc2Sc2c1cccc2-c1ccc(cc1)-n1c2ccccc2c2ccccc12 RRDTWBBIYVHARV-UHFFFAOYSA-N 0.000 description 1
- LZSJBLXYNYSKPJ-UHFFFAOYSA-N 9-octyl-9h-fluorene Chemical compound C1=CC=C2C(CCCCCCCC)C3=CC=CC=C3C2=C1 LZSJBLXYNYSKPJ-UHFFFAOYSA-N 0.000 description 1
- 229910018134 Al-Mg Inorganic materials 0.000 description 1
- 229910018467 Al—Mg Inorganic materials 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910008266 Li-Ag Inorganic materials 0.000 description 1
- 229910008445 Li—Ag Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229910006501 ZrSiO Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- IUFDZNVMARBLOJ-UHFFFAOYSA-K aluminum;quinoline-2-carboxylate Chemical compound [Al+3].C1=CC=CC2=NC(C(=O)[O-])=CC=C21.C1=CC=CC2=NC(C(=O)[O-])=CC=C21.C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IUFDZNVMARBLOJ-UHFFFAOYSA-K 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
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- 230000000903 blocking effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 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
- VVOPUZNLRVJDJQ-UHFFFAOYSA-N phthalocyanine copper Chemical compound [Cu].C12=CC=CC=C2C(N=C2NC(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2N1 VVOPUZNLRVJDJQ-UHFFFAOYSA-N 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- FZEWPLIHPXGNTB-UHFFFAOYSA-N thianthren-1-ylboronic acid Chemical compound S1C2=CC=CC=C2SC2=C1C=CC=C2B(O)O FZEWPLIHPXGNTB-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
-
- 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
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
【選択図】なし
Description
正孔輸送材料の一種は、少なくとも2つの芳香族三級アミン部分(例えば、ビフェニルジアミンに基づくもの、もしくは、「スターバースト」構造のもの)を含む芳香族第三級アミンを含む。以下の化合物が芳香族第三級アミンの代表的な化合物であり、現時点では、α−NPB(Tg(℃)98、μh(cm2V−1s−1)1×10−4)が、商業生産にて最も広く受け入れられ、使用されていると考えられている。
R2とR3は、1〜5のアリール環(多環アリール、もしくは、アリール置換された多環アリールを含む)基、アラルキル環基もしくはヘテロアリール環基を形成し、これらは、1つ以上のC1-C4アルキル置換基もしくはC1-C4アルコキシ置換基で置換されても良い。上記の式の化合物は、単体で用いられても良く、また、リチウムキノラートもしくはジルコニウムキノラートなどのキノラートのような、他の電子注入物質と組み合わせて用いられても良い。シッフ塩基は、好ましくは、電子注入層の少なくとも30重量%であり、より好ましくは、少なくとも50重量%である。
<2,8-ジブロモジベンゾチオフェンの合成>
結果 : C, 70.10; H, 3.41; S, 26.53.
C36H20S5の理論値:C, 70.55; H, 3.29; S, 26.16 %.
UV: λmax/nm (ε) (CH2Cl2);294(sh)(30,989)、263(97,473)および230(35,934)
UV: λmax/nm (薄膜); 303 と268;
バンドギャップ: 3.85 eV
FL: λmax/nm(ε) (CH2Cl2); 441 (励起波長: 350 nm),
λmax/nm(ε) (粉末) 439 (励起波長: 350 nm);
λmax/nm(ε) (薄膜), 434, (励起波長: 350 nm)
CV: 電解質(lOOmM-テトラブチルアンモニウムテトラフルオロボラート)、被検物質(1 mM)、溶媒-ジクロロメタン:
HOMO:-6.06 eV および LUMO:-2.2 eV 薄膜の光吸収端から計算
TGA/℃(% 重量減少):486(5)および510(10)
<2-(4'-ジフェニルアミノ)フェニル-8-(1'-チアントレニル)-ジベンゾチオフェン (HTS−11)>
結果 : C 79.37, H 3.67, N 2.45, S 16.04 %,
以下の分析結果も得られた: C 77.52, H 4.13, N 1.89 および S 16.04 %
C42H27NS3の理論値:C 78.59, H 4.24, N 2.18 および S 14.99 %.
UV:λmax(CH2Cl2)/nm (ε/dm3mol-1cm-1)
338 (25,536) 291 sh(30,643) および 261(72,321).
λmax(薄膜)/nm: 336 sh, 291(sh) および 261 nm.
光学バンドギャップ: 3.26 eV
FL:λmax /nm(CH2Cl2)em: 413; ex/nm: 300;
λmax /nm(粉末)em: 419, ex/nm: 300;
λmax/nm(薄膜) em: 414, ex/nm: 300.
TGA/℃(% 重量減少): 461 (1%) および 509 (5)
<4-(1-チアントレニル)-ビス(トリフェニルアミン) (HTS−13)>
結果: C 81.20, H 4.80, N 3.93, S 10.16 %.
C48H34N2S2の理論値, C 82.02, H 4.88, N 3.98 および S 9.12 %.
UV: λmax(トルエン)/nm (ε/dm3mol-1cm-1) 324.50 (36,506).
λmax (薄膜)/nm: 324.50 および 265.50 nm
光学バンドギャップ: 3.1 eV
FL: λmax/nm(トルエン)em: 394 および 410(sh); ex/nm: 320;
λmax /nm(粉末)em: 427, ex/nm: 320;
λmax /nm(薄膜) em: 428 および 410 (sh), ex/nm: 320.
TGA/℃(% 重量減少): 382 (5) および Td 498℃
<OLEDデバイスの効率>
正孔輸送層にα―NPB、HTS−8、HTS−11を用いたOLEDが製造された。層は以下の通りである(ここで、HILは正孔注入層を意味し、HTLは正孔輸送層を意味し、EMLは発光層を意味し、さらに、ELTは電子輸送層を意味する)。
アノード: ガラス上のITO
HIL : PEDOT:PSS 約40nm、スピンコーティング
HTL : NPB(50nm)、HTS−8(10〜22nm)、
もしくは、HTS−11(10〜30nm)
EML : TCTA:TPBi(3:7):Ir(ppy)2acac、10%ドープ
ETL : TPBi(30nm)
カソード:LiF(0.5nm)/Al(100nm)
る。
Claims (28)
- 2-(4'-ジフェニルアミノ)フェニル-8-(1'-チアントレニル)-ジベンゾチオフェン。
- 4-(1-チアントレニル)-ビス(トリフェニルアミン)。
- 昇華によって精製される、請求項1もしくは2に記載の化合物。
- 請求項1、2、もしくは、3に記載する化合物、ならびに、アクセプタ型の有機分子であるp-ドーパントを含む、正孔輸送物質。
- 前記ドーパントが、前記物質が層を形成するために蒸着される場合に前記ドーパントが前記層の厚さの約10〜40%に寄与する量だけ存在する、請求項4に記載の物質。
- 前記ドーパントが、前記物質が層を形成するために蒸着される場合に前記ドーパントが前記層の厚さの約33%に寄与する量だけ存在する、請求項5に記載の物質。
- 前記ドーパントが、テトラシアノキノジメタン、もしくは、テトラフルオロテトラシアノ-キノジメタンを含む、請求項4〜6のいずれかに記載の物質。
- 一般式が以下の(i)〜(vii)のいずれかである化合物を含む、請求項4〜7のいずれかに記載の物質。
式(i)では、メチル基は、C1〜C4アルキル基、または、単環式アリール基、もしくは、多環式アリール基、または、ヘテロアリール基で置換されても良く、これらの基が、さらに、例えばアルキル基、アリール基もしくはアリールアミノ基、あるいは、式(viii)もしくは(ix)などでさらに置換されても良く、
- α−NPBもしくはβ−NPBである三級アミンを含む、請求項8に記載の物質。
- 第1の電極および第2の電極と、前記第1の電極と前記第2の電極の間にあり、請求項1〜3のいずれかに記載の化合物、もしくは、請求項4〜9のいずれかに記載の物質を含む層と、
を有する光学発光ダイオード。 - 前記層は正孔輸送層である、請求項10に記載のデバイス。
- 蛍光発光体を含む発光層を有する、請求項10または11に記載のデバイス。
- りん光発光体を含む発光層を有する、請求項10または11に記載のデバイス。
- イオン蛍光性の(希土類元素をベースとした)発光体を含む発光層を有する、請求項10または11に記載のデバイス。
- 量子ドットを含む発光層を有する、請求項10または11に記載のデバイス。
- 熱活性蛍光(TADF)物質を含む発光層を有する、請求項10または11に記載のデバイス。
- CuPC、ZnTpTP、2-TNATA、もしくは、以下の化合物を含む正孔注入層を有する、請求項10〜16のいずれかに記載のデバイス。
- フラットパネルディスプレイの一部を形成する、請求項10〜17のいずれかに記載のデバイス。
- ライティングパネルの一部を形成する、請求項10〜17のいずれかに記載のデバイス。
- 請求項1〜3のいずれかに記載の化合物、もしくは、請求項4〜9のいずれかに記載の物質を含む、有機光発電デバイス。
- 請求項1〜3のいずれかに記載の化合物、もしくは、請求項4〜9のいずれかに記載の物質を含む、静電潜像デバイスを形成するイメージング部材。
- 請求項1〜3のいずれかに記載の化合物、もしくは、請求項4〜9のいずれかに記載の物質を含む、有機薄膜トランジスタ。
- 請求項1〜3のいずれかに記載の化合物、もしくは、請求項4〜9のいずれかに記載の物質を含む、色素増感太陽電池デバイス。
- 請求項1〜13のいずれかに記載の化合物、もしくは、請求項4〜9のいずれかに記載の物質を含む、プリントデバイス。
- 請求項1〜3のいずれかに記載の化合物、もしくは、請求項4〜9のいずれかに記載の物質を含む、量子ドットに基づくエレクトロルミネセンスデバイス。
- 請求項1もしくは2に記載の化合物を含む正孔輸送層を有する、請求項25に記載のデバイス。
- 請求項1〜3のいずれかに記載の化合物、もしくは、請求項4〜9のいずれかに記載の物質を含み、導電性、抵抗性、誘電性、圧電性、もしくは、焦電気性のフィルム、配線、または、グリッドにプリントを行う光源として使用されるOLEDデバイス。
- 請求項1〜3のいずれかに記載の化合物、もしくは、請求項4〜9のいずれかに記載の物質を含む、OLEDライティングパネル。
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Application Number | Priority Date | Filing Date | Title |
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GB1512720.2A GB2543732A (en) | 2015-07-20 | 2015-07-20 | Heterocyclic compounds and their use in electro-optical or opto-electronic devices |
GB1512720.2 | 2015-07-20 | ||
PCT/GB2016/052176 WO2017013420A1 (en) | 2015-07-20 | 2016-07-19 | Heterocyclic compounds and their use in electro-optical or opto-electronic devices |
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JP2018524379A true JP2018524379A (ja) | 2018-08-30 |
JP6779973B2 JP6779973B2 (ja) | 2020-11-04 |
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US (1) | US20190123283A1 (ja) |
EP (1) | EP3325463B1 (ja) |
JP (1) | JP6779973B2 (ja) |
KR (1) | KR20180030202A (ja) |
CN (1) | CN107849005A (ja) |
BR (1) | BR112018000721A2 (ja) |
GB (1) | GB2543732A (ja) |
HK (1) | HK1250712A1 (ja) |
WO (1) | WO2017013420A1 (ja) |
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KR102375620B1 (ko) * | 2017-10-16 | 2022-03-16 | 엘지디스플레이 주식회사 | 발광다이오드 및 이를 포함하는 발광장치 |
KR102371410B1 (ko) * | 2017-10-26 | 2022-03-04 | 엘지디스플레이 주식회사 | 발광다이오드 및 이를 포함하는 발광장치 |
CN108550614B (zh) * | 2018-05-31 | 2020-03-13 | 上海天马有机发光显示技术有限公司 | 有机发光显示面板及其显示装置 |
KR102678514B1 (ko) * | 2018-12-05 | 2024-06-25 | 엘지디스플레이 주식회사 | 유기 화합물, 이를 포함하는 발광다이오드 및 발광장치 |
KR20200132537A (ko) | 2019-05-17 | 2020-11-25 | 삼성전자주식회사 | 광전 변환 소자, 유기 센서 및 전자 장치 |
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US5466551A (en) * | 1994-11-15 | 1995-11-14 | Xerox Corporation | Image member including a grounding layer |
DE60033038T2 (de) * | 2000-11-24 | 2007-08-23 | Sony Deutschland Gmbh | Hybridsolarzelle mit thermisch abgeschiedener Halbleiteroxidschicht |
JP4384536B2 (ja) * | 2004-04-27 | 2009-12-16 | 三井化学株式会社 | アントラセン化合物、および該アントラセン化合物を含有する有機電界発光素子 |
KR100679724B1 (ko) * | 2004-10-13 | 2007-02-07 | 주식회사 두산 | 전계 발광 소자용 발색 화합물 및 이를 포함하는 유기전계 발광소자 |
TW200621933A (en) * | 2004-12-30 | 2006-07-01 | Au Optronics Corp | Structure of organic light emitting device |
JP2009267255A (ja) * | 2008-04-28 | 2009-11-12 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
CN102131891B (zh) * | 2008-06-30 | 2014-01-29 | 通用显示公司 | 具有含硫基团的空穴传输材料 |
US8969592B2 (en) * | 2012-01-10 | 2015-03-03 | Universal Display Corporation | Heterocyclic host materials |
US9054323B2 (en) * | 2012-03-15 | 2015-06-09 | Universal Display Corporation | Secondary hole transporting layer with diarylamino-phenyl-carbazole compounds |
KR102029336B1 (ko) * | 2012-08-21 | 2019-10-07 | 제일모직 주식회사 | 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치 |
KR20140035737A (ko) * | 2012-09-14 | 2014-03-24 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR102024117B1 (ko) * | 2012-09-17 | 2019-09-24 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
EP3806176A1 (de) * | 2012-10-31 | 2021-04-14 | Merck Patent GmbH | Elektronische vorrichtung |
GB201306365D0 (en) * | 2013-04-09 | 2013-05-22 | Kathirgamanathan Poopathy | Heterocyclic compounds and their use in electro-optical or opto-electronic devices |
CN103346265B (zh) * | 2013-06-21 | 2016-01-06 | 深圳市华星光电技术有限公司 | 一种发光器件、显示面板及其制造方法 |
JP6530318B2 (ja) * | 2013-11-28 | 2019-06-12 | 株式会社Kyulux | 発光材料、有機発光素子および化合物 |
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2015
- 2015-07-20 GB GB1512720.2A patent/GB2543732A/en not_active Withdrawn
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2016
- 2016-07-19 EP EP16744468.6A patent/EP3325463B1/en not_active Not-in-force
- 2016-07-19 CN CN201680042510.2A patent/CN107849005A/zh active Pending
- 2016-07-19 JP JP2018502225A patent/JP6779973B2/ja not_active Expired - Fee Related
- 2016-07-19 BR BR112018000721A patent/BR112018000721A2/pt not_active Application Discontinuation
- 2016-07-19 KR KR1020187004865A patent/KR20180030202A/ko unknown
- 2016-07-19 WO PCT/GB2016/052176 patent/WO2017013420A1/en active Application Filing
- 2016-07-19 US US15/746,347 patent/US20190123283A1/en not_active Abandoned
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2018
- 2018-08-07 HK HK18110148.0A patent/HK1250712A1/zh unknown
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Publication number | Publication date |
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US20190123283A1 (en) | 2019-04-25 |
GB2543732A (en) | 2017-05-03 |
HK1250712A1 (zh) | 2019-01-11 |
WO2017013420A1 (en) | 2017-01-26 |
GB201512720D0 (en) | 2015-08-26 |
JP6779973B2 (ja) | 2020-11-04 |
EP3325463A1 (en) | 2018-05-30 |
BR112018000721A2 (pt) | 2018-09-04 |
CN107849005A (zh) | 2018-03-27 |
KR20180030202A (ko) | 2018-03-21 |
EP3325463B1 (en) | 2019-06-05 |
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