JP5591800B2 - トリフェニレンを含有するホール輸送材料 - Google Patents
トリフェニレンを含有するホール輸送材料 Download PDFInfo
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- JP5591800B2 JP5591800B2 JP2011516801A JP2011516801A JP5591800B2 JP 5591800 B2 JP5591800 B2 JP 5591800B2 JP 2011516801 A JP2011516801 A JP 2011516801A JP 2011516801 A JP2011516801 A JP 2011516801A JP 5591800 B2 JP5591800 B2 JP 5591800B2
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- 239000000463 material Substances 0.000 title claims description 83
- 230000005525 hole transport Effects 0.000 title claims description 31
- 125000005580 triphenylene group Chemical group 0.000 title claims description 25
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 title claims description 17
- 239000000203 mixture Substances 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 8
- 239000002019 doping agent Substances 0.000 claims description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 229930192474 thiophene Natural products 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002524 organometallic group Chemical group 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 66
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 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 9
- 239000007924 injection Substances 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
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- 0 *N(*)c(cc1)ccc1-c(cc1)ccc1N(*)* Chemical compound *N(*)c(cc1)ccc1-c(cc1)ccc1N(*)* 0.000 description 3
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- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 3
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
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- 239000002904 solvent Substances 0.000 description 3
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FAWPKVGTGSNUMQ-UHFFFAOYSA-N Cc(cc1)ccc1-c1ccc(c2ccccc2c2c3cccc2)c3c1 Chemical compound Cc(cc1)ccc1-c1ccc(c2ccccc2c2c3cccc2)c3c1 FAWPKVGTGSNUMQ-UHFFFAOYSA-N 0.000 description 2
- BOJZSXCXPRENSQ-UHFFFAOYSA-N Cc1cccc(-c(cc2)cc3c2c2ccccc2c2ccccc32)c1 Chemical compound Cc1cccc(-c(cc2)cc3c2c2ccccc2c2ccccc32)c1 BOJZSXCXPRENSQ-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
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- 238000013461 design Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical group [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- MWRPTYPXCLUMLH-UHFFFAOYSA-N n-phenyltriphenylen-2-amine Chemical compound C=1C=C2C3=CC=CC=C3C3=CC=CC=C3C2=CC=1NC1=CC=CC=C1 MWRPTYPXCLUMLH-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010129 solution processing Methods 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- HQJQYILBCQPYBI-UHFFFAOYSA-N 1-bromo-4-(4-bromophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(Br)C=C1 HQJQYILBCQPYBI-UHFFFAOYSA-N 0.000 description 1
- GEDOYYDMCZUHNW-UHFFFAOYSA-N 2-bromotriphenylene Chemical group C1=CC=C2C3=CC(Br)=CC=C3C3=CC=CC=C3C2=C1 GEDOYYDMCZUHNW-UHFFFAOYSA-N 0.000 description 1
- ABZLRYFYOFGCRQ-UHFFFAOYSA-N 2-methyl-1h-quinoline-2,8-diol Chemical compound C1=CC=C2C=CC(C)(O)NC2=C1O ABZLRYFYOFGCRQ-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical group C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- KTCJNXNAXQFFKU-UHFFFAOYSA-N 4-(4-aminophenyl)aniline Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1.C1=CC(N)=CC=C1C1=CC=C(N)C=C1 KTCJNXNAXQFFKU-UHFFFAOYSA-N 0.000 description 1
- CCIVUDMVXNBUCY-UHFFFAOYSA-N 4-bromo-n-phenylaniline Chemical compound C1=CC(Br)=CC=C1NC1=CC=CC=C1 CCIVUDMVXNBUCY-UHFFFAOYSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical group CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- PAMZIIXCCCIZJR-UHFFFAOYSA-N C1(=CC=CC=C1)N(C1=CC=C(C=C1)B(O)O)C1=CC=CC=C1.C1(=CC=CC=C1)C=1C(=C(C(=C(C1)C1=CC=C(C=C1)N)C1=CC=CC=C1)C1=CC=CC=C1)N Chemical compound C1(=CC=CC=C1)N(C1=CC=C(C=C1)B(O)O)C1=CC=CC=C1.C1(=CC=CC=C1)C=1C(=C(C(=C(C1)C1=CC=C(C=C1)N)C1=CC=CC=C1)C1=CC=CC=C1)N PAMZIIXCCCIZJR-UHFFFAOYSA-N 0.000 description 1
- QYDFVOUIKGDOHM-UHFFFAOYSA-N C1=C(C=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)C=1C=C(C=CC1)C1(CC=C(C=C1)C1=CC=C(C=C1)N)N Chemical compound C1=C(C=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)C=1C=C(C=CC1)C1(CC=C(C=C1)C1=CC=C(C=C1)N)N QYDFVOUIKGDOHM-UHFFFAOYSA-N 0.000 description 1
- WGQZOLTVHMAVPU-UHFFFAOYSA-N C[IH]C1=CC(c(cc2)cc3c2c2ccccc2c2ccccc32)=CCC1 Chemical compound C[IH]C1=CC(c(cc2)cc3c2c2ccccc2c2ccccc32)=CCC1 WGQZOLTVHMAVPU-UHFFFAOYSA-N 0.000 description 1
- ATVWBNMHOBUNKM-UHFFFAOYSA-N Ic1ccc(C2C=C(c3ccccc3-c3ccccc33)C3=CC2)cc1 Chemical compound Ic1ccc(C2C=C(c3ccccc3-c3ccccc33)C3=CC2)cc1 ATVWBNMHOBUNKM-UHFFFAOYSA-N 0.000 description 1
- CECYSNVBDZBOJN-UHFFFAOYSA-N N-[1-phenyl-4-[4-(N-(3-triphenylen-2-ylphenyl)anilino)phenyl]cyclohexa-2,4-dien-1-yl]-3-triphenylen-2-ylaniline Chemical compound C1(=CC=CC=C1)C1(CC=C(C=C1)C1=CC=C(C=C1)N(C1=CC(=CC=C1)C1=CC=2C3=CC=CC=C3C3=CC=CC=C3C=2C=C1)C1=CC=CC=C1)NC1=CC(=CC=C1)C1=CC=2C3=CC=CC=C3C3=CC=CC=C3C=2C=C1 CECYSNVBDZBOJN-UHFFFAOYSA-N 0.000 description 1
- LRHYQVYYQKQABO-UHFFFAOYSA-N N-[1-phenyl-4-[4-(N-triphenylen-2-ylanilino)phenyl]cyclohexa-2,4-dien-1-yl]triphenylen-2-amine Chemical compound C1(=CC=CC=C1)C1(CC=C(C=C1)C1=CC=C(C=C1)N(C1=CC=2C3=CC=CC=C3C3=CC=CC=C3C=2C=C1)C1=CC=CC=C1)NC1=CC=2C3=CC=CC=C3C3=CC=CC=C3C=2C=C1 LRHYQVYYQKQABO-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- FDRNXKXKFNHNCA-UHFFFAOYSA-N c(cc1)ccc1Nc(cc1)ccc1-c(cc1)ccc1Nc1ccccc1 Chemical compound c(cc1)ccc1Nc(cc1)ccc1-c(cc1)ccc1Nc1ccccc1 FDRNXKXKFNHNCA-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
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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
- H10K85/631—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
- C07C211/55—Diphenylamines
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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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]
- H10K50/14—Carrier transporting layers
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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
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/28—Phenalenes; Hydrogenated phenalenes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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Description
本発明は新規材料に関する。より具体的には、本発明は有機発光デバイス(OLED)において有用な新規材料に関する。
有機材料を使用する光電子デバイスは多くの理由のためますます望ましくなっている。このようなデバイスを作製するのに用いられる材料の多くは比較的安価であり、従って有機光電子デバイスは無機デバイスに対する費用優位の可能性を有する。加えて、有機材料の特有の性質、例えばその柔軟性、はこれらをフレキシブル基板の製造のような特定の用途によく適させるであろう。有機光電子デバイスの例は有機発光デバイス(OLED)、有機フォトトランジスタ、有機光電池および有機光検出器を含む。OLEDについて、有機材料は従来材料を上回る性能優位性を有するであろう。例えば、有機発光層が発光する波長は一般的に適切なドーパントにより容易に調整されるであろう。
一般的に、OLEDは陽極と陰極との間に配置され電子的に接続されている少なくとも1つの有機層を有する。電流を流すと、陽極はホールをおよび陰極は電子を有機層に注入する。注入されたホールおよび電子は逆に帯電した電極に向かってそれぞれ移動する。電子とホールとが同じ分子に局在する場合には、励起エネルギー状態を有する局在した電子−ホールペアである「エキシトン」を生じる。エキシトンが光電子放出メカニズムにより緩和すると発光する。ある場合には、エキシトンはエキシマーまたはエキシプレックスに局在していてもよい。熱緩和のような非放射性メカニズムも起こりうるが、一般的には望ましくないと考えられる。
4−(ジフェニルアミノ)フェニルボロン酸(4.87g,16.8mmol)、4−ブロモ−N−フェニルアニリン(3.5g,14mmol)、リン酸カリウム(9.2g,42mmol)、ジシクロヘキシル(2’,6’−ジメトキシビフェニル−2−イル)ホスフィン(0.23g,0.56mmol)を3つ首フラスコに窒素下で加えた。続いて200mLのトルエンおよび20mLの水を加えた。溶液を窒素を用いて20分間脱気した。Pd2(dba)3(0.13g,0.14mmol)を混合物に加えた。その後混合物を加熱して終夜還流させた。室温まで冷やした後、有機相を分離して硫酸マグネシウムにて乾燥させた。溶媒を蒸発させた後、残渣を溶離剤として1:2のジクロロメタンとヘキサンとを用いるカラムクロマトグラフィーにより精製した。4.7gの所望生成物を得た(81%収率)。
N4,N4,N4’−トリフェニル−N4’−(3−(トリフェニレン−2−イル)フェニル)ビフェニル−4,4’−ジアミンPd2(dba)3(0.07g,0.07mmol)およびジシクロヘキシル(2’,6’−ジメトキシビフェニル−2−イル)ホスフィン(0.13g,0.3mmol)を3つ首フラスコに窒素下で加えた。続いて150mLのキシレンを加えた。溶液を窒素下で20分間撹拌した。この溶液に3−(トリフェニレン−2−イル)フェニルトリフルオロメタンスルホナート(3.87g,8.5mmol)、ナトリウムtert−ブトキシド(1.1g,11.6mmol)およびN4,N4,N4’−トリフェニルビフェニル−4,4’−ジアミン(3.2g,7.7mmol)を順番に加えた。その後混合物を加熱して終夜還流させた。室温まで冷やした後、300mLのジクロロメタンを溶液に加えた。続いて溶液をセライト床を通してろ過した。溶媒を蒸発させた後、残渣を溶離剤として1:3のジクロロメタンとヘキサンとを用いるカラムクロマトグラフィーにより精製した。3.5gの所望生成物を精製後に得た。この生成物を高真空昇華によりさらに精製した(64%収率)。
N4,N4’−ジフェニル−N4,N4’−ビス(3−(トリフェニレン−2−イル)フェニル)ビフェニル−4,4’−ジアミンPd2(dba)3(0.1g,0.1mmol)およびジシクロヘキシル(2’,6’−ジメトキシビフェニル−2−イル)ホスフィン(0.17g,0.4mmol)を3つ首フラスコに窒素下で加えた。続いて150mLのキシレンを加えた。溶液を窒素下で20分間撹拌した。この溶液に3−(トリフェニレン−2−イル)フェニルトリフルオロメタンスルホナート(5.0g,11.1mmol)、ナトリウムtert−ブトキシド(1.5g,15mmol)およびN4,N4’−ジフェニルビフェニル−4,4’−ジアミン(1.7g,5mmol)を順番に加えた。その後混合物を加熱して終夜還流させた。室温にまで冷やした後、混合物は300mLのメタノールから沈殿した。固体をろ過により集めた。続いて固体をジクロロメタンに再溶解させて硫酸マグネシウムにて乾燥させた。溶媒を蒸発させた後、4.4gの所望生成物を得た。化合物を高真空昇華によりさらに精製した。
酢酸パラジウム(0.01g,0.06mmol)およびトルエン中1.0Mのトリ(t−ブチル)ホスフィン溶液(0.02mL,0.02mmol)を3つ首フラスコに窒素下で加えた。続いて100mLのトルエンを加えた。色が消えるまで溶液を窒素下で撹拌した。この溶液に2−ブロモトリフェニレン(2g,6.5mmol)、ナトリウムtert−ブトキシド(0.94g,9.8mmol)およびアニリン(1.8g,20mmol)を順番に加えた。その後混合物を加熱して終夜還流させた。室温にまで冷やした後、混合物をセライト床を通してろ過してジクロロメタンで十分に洗浄した。生成物を溶離剤として1:7のジクロロメタンとヘキサンとを用いるカラムクロマトグラフィーにより精製した。0.8gの所望生成物を精製後に得た。
N4,N4’−ジフェニル−N4,N4’−ジ(トリフェニレン−2−イル)ビフェニル−4,4’−ジアミンパラジウムアセタート(0.2mg,0.03mmol)およびトルエン中1.0Mのトリ(t−ブチル)ホスフィン溶液(0.1mL,0.1mmol)を3つ首フラスコに窒素下で加えた。続いて60mLのキシレンを加えた。色が消えるまで溶液を窒素下で撹拌した。この溶液に4,4’−ジブロムビフェニル(dibrombiphenyl)(0.33g,1mmol)、ナトリウムtert−ブトキシド(0.3g,3mmol)およびN−フェニルトリフェニレン−2−アミン(0.7g,2.2mmol)を順番に加えた。その後混合物を加熱して終夜還流させた。室温にまで冷やした後に、混合物をセライト床を通してろ過してジクロロメタンで十分に洗浄した。生成物を溶離剤として1:2のジクロロメタンとヘキサンとを用いるカラムクロマトグラフィーにより精製した。0.4gの所望生成物を精製後に得た。生成物を高真空昇華によりさらに精製した。
デバイスを標準的な技術を用いて作製した。デバイスは図1に示すものと同様の構造を有するが、表に記載する具体的な層と材料とを含む。Cmpd.は化合物の省略形である。Ex.は例の省略形である。
例1(比較)と例2との間の違いは例1はα−NPD HTLを有し、一方で例2は化合物C−1のHTLを有することである。HTL C−1とホストとしての化合物2との組み合わせはα−NPD HTLを用いる同様のデバイスよりも優れた結果を与える。例2はデバイス電圧、発光効率および寿命における優れた性能を示す。さらに、例2の結果は一般に緑色発光デバイスについて特に良好であり、C−1と同様の化合物を有するHTLと化合物2と同様のホストとを組み合わせることの望ましさを示している。
例3(比較)と例4との間の違いは例3はα−NPD HTLを有し、一方で例4は化合物C−1のHTLを有することである。ホール注入層(HIL)における違いも存在する。HTL C−1とホストとしての化合物3との組み合わせはα−NPD HTLを用いる同様のデバイスよりも優れた結果を示す。例4は効率および寿命における優れた性能を示す。さらに、例4の結果は一般に緑色発光デバイスについて特に良好であり、C−1と同様の化合物を有するHTLと化合物3と同様のホストとを組み合わせることの望ましさを示している。
LG−201の代わりにAlq3のETLを用いることを除いては、グループ3はグループ2においてしたものと同様の比較をした。グループ2からと同じ結論をグループ3から得ることができる。
例7(比較)と例8および9との間の違いは例7はNPD HTLを有し、一方で例8および9は化合物C−1およびA−1のHTLをそれぞれ有することである。すべてのHTLをBAlqホストと組み合わせて示す。例8および9はα−NPD HTL比較例7に対して効率および寿命の点ではより低い性能を示す。しかしながら、例8および9のデバイスの性能は市販のデバイスについて求められるものよりもなお十分に高い。
化合物1の代わりにLG−101のHILを用いることを除いては、グループ5はグループ4においてしたものと同様の比較をする。グループ4からと同じ結論をグループ5から得ることができる。
Claims (20)
- 以下を備える有機発光デバイス:
陽極;
陰極;
前記陽極と前記陰極との間に配置された有機発光層であって,前記有機発光層はホストおよびリン光を発するドーパントをさらに含む;
前記有機発光層と前記陽極との間に配置され、前記有機発光層と直接接触するホール輸送材料を含む有機ホール輸送層;
ここで前記ホール輸送材料は以下の構造を有する:
ここでR1、R2、R3およびR4の少なくとも1つは以下からなる群から選択される:
ここでR1、R2、R3およびR4のそれぞれはR1、R2、R3およびR4と縮合しない置換基でさらに置換されていてもよい。 - 前記ドーパントが有機金属イリジウム材料である請求項12に記載のデバイス。
- 前記ホストがトリフェニレン含有ベンゾ縮合チオフェンを含む化合物である請求項12に記載のデバイス。
- 前記ホストがアリールトリフェニレン化合物である請求項12に記載のデバイス。
- 消費者製品であって、前記消費者製品は有機発光デバイスを含み、これはさらに以下の化学構造を有する物質の組成物を含む:
ここでR1、R2、R3およびR4のそれぞれは以下からなる群から独立して選択される:
ここでR1、R2、R3およびR4の少なくとも1つは以下からなる群から選択される:
ここでR1、R2、R3およびR4のそれぞれはR1、R2、R3およびR4と縮合しない置換基でさらに置換されていてもよい。
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