JP5442200B2 - エレクトロルミネセンスポリマー - Google Patents
エレクトロルミネセンスポリマー Download PDFInfo
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- JP5442200B2 JP5442200B2 JP2007519714A JP2007519714A JP5442200B2 JP 5442200 B2 JP5442200 B2 JP 5442200B2 JP 2007519714 A JP2007519714 A JP 2007519714A JP 2007519714 A JP2007519714 A JP 2007519714A JP 5442200 B2 JP5442200 B2 JP 5442200B2
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- polymer
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- 229920000642 polymer Polymers 0.000 title claims description 108
- 229920001577 copolymer Polymers 0.000 claims description 48
- 229910052751 metal Inorganic materials 0.000 claims description 28
- 239000002184 metal Substances 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 21
- 239000003446 ligand Substances 0.000 claims description 19
- 239000000178 monomer Substances 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 11
- 239000000412 dendrimer Substances 0.000 claims description 10
- 229920000736 dendritic polymer Polymers 0.000 claims description 10
- 229910052741 iridium Inorganic materials 0.000 claims description 10
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229920000547 conjugated polymer Polymers 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical class C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 claims description 6
- -1 aryl silane Chemical compound 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- 150000003384 small molecules Chemical class 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 230000007704 transition Effects 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 4
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- ZIZMDHZLHJBNSQ-UHFFFAOYSA-N 1,2-dihydrophenazine Chemical class C1=CC=C2N=C(C=CCC3)C3=NC2=C1 ZIZMDHZLHJBNSQ-UHFFFAOYSA-N 0.000 claims description 2
- XDFUNRTWHPWCKO-UHFFFAOYSA-N 4,5,9,10-tetrahydropyrene Chemical class C1CC2=CC=CC3=C2C2=C1C=CC=C2CC3 XDFUNRTWHPWCKO-UHFFFAOYSA-N 0.000 claims description 2
- WPCIUCNVWJNRCD-UHFFFAOYSA-N 4,5-dihydropyrene Chemical class C1=CC=C2CCC3=CC=CC4=CC=C1C2=C34 WPCIUCNVWJNRCD-UHFFFAOYSA-N 0.000 claims description 2
- XXPBFNVKTVJZKF-UHFFFAOYSA-N 9,10-dihydrophenanthrene Chemical class C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001454 anthracenes Chemical class 0.000 claims description 2
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 150000001545 azulenes Chemical class 0.000 claims description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 2
- 239000013522 chelant Substances 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- 150000002220 fluorenes Chemical class 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 150000002240 furans Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 150000004866 oxadiazoles Chemical class 0.000 claims description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 2
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 2
- 150000005030 phenoxathiins Chemical class 0.000 claims description 2
- 125000001644 phenoxazinyl group Chemical class C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 2
- 150000003216 pyrazines Chemical class 0.000 claims description 2
- 150000003220 pyrenes Chemical class 0.000 claims description 2
- 150000004892 pyridazines Chemical class 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims description 2
- 150000003233 pyrroles Chemical class 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 150000003248 quinolines Chemical class 0.000 claims description 2
- 150000003252 quinoxalines Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 claims description 2
- 150000005029 thianthrenes Chemical class 0.000 claims description 2
- 150000003577 thiophenes Chemical class 0.000 claims description 2
- 125000005259 triarylamine group Chemical group 0.000 claims description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 2
- 150000008365 aromatic ketones Chemical class 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 claims 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims 1
- 150000001716 carbazoles Chemical class 0.000 claims 1
- 150000004827 dibenzo-1,4-dioxins Chemical class 0.000 claims 1
- 238000004770 highest occupied molecular orbital Methods 0.000 claims 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical class [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 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- 238000000034 method Methods 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- 150000004696 coordination complex Chemical class 0.000 description 12
- 230000008901 benefit Effects 0.000 description 7
- 238000005401 electroluminescence Methods 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 150000002503 iridium Chemical class 0.000 description 5
- 150000002504 iridium compounds Chemical class 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 229920001109 fluorescent polymer Polymers 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 150000002987 phenanthrenes Chemical class 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- LYQPPYHBGKQNCF-UHFFFAOYSA-N 1-(3-bromophenyl)isoquinoline iridium 1-phenylisoquinoline Chemical compound [Ir].c1ccc(cc1)-c1nccc2ccccc12.Brc1cccc(c1)-c1nccc2ccccc12.Brc1cccc(c1)-c1nccc2ccccc12 LYQPPYHBGKQNCF-UHFFFAOYSA-N 0.000 description 2
- RXACYPFGPNTUNV-UHFFFAOYSA-N 9,9-dioctylfluorene Chemical compound C1=CC=C2C(CCCCCCCC)(CCCCCCCC)C3=CC=CC=C3C2=C1 RXACYPFGPNTUNV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- NDUYVVIORORQSV-UHFFFAOYSA-N [Ir].Brc1cccc(c1)-c1nccc2ccccc12.Brc1cccc(c1)-c1nccc2ccccc12.Brc1cccc(c1)-c1nccc2ccccc12 Chemical compound [Ir].Brc1cccc(c1)-c1nccc2ccccc12.Brc1cccc(c1)-c1nccc2ccccc12.Brc1cccc(c1)-c1nccc2ccccc12 NDUYVVIORORQSV-UHFFFAOYSA-N 0.000 description 2
- SYCLNCMMKMFNBA-UHFFFAOYSA-N [Ir]c1ncccc1-c1cc2ccccc2s1.Brc1cccc(c1)-c1nccc2ccccc12.Brc1cccc(c1)-c1nccc2ccccc12 Chemical compound [Ir]c1ncccc1-c1cc2ccccc2s1.Brc1cccc(c1)-c1nccc2ccccc12.Brc1cccc(c1)-c1nccc2ccccc12 SYCLNCMMKMFNBA-UHFFFAOYSA-N 0.000 description 2
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 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 1
- GODFYRLYJQMVAD-UHFFFAOYSA-N C1=CC=CC=C1C1=CC=CN=C1[Ir](C=1C(=CC=CN=1)C=1C=CC=CC=1)C1=NC=CC=C1C1=CC=CC=C1 Chemical compound C1=CC=CC=C1C1=CC=CN=C1[Ir](C=1C(=CC=CN=1)C=1C=CC=CC=1)C1=NC=CC=C1C1=CC=CC=C1 GODFYRLYJQMVAD-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000005264 aryl amine group Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 229920005605 branched copolymer Polymers 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 150000004697 chelate complex Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229920001114 fluorescent copolymer Polymers 0.000 description 1
- 239000003574 free electron Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 1
- DGQPXSGKGUYXGA-UHFFFAOYSA-N iridium(3+);2-phenylpyridine Chemical class [Ir+3].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 DGQPXSGKGUYXGA-UHFFFAOYSA-N 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000000504 luminescence detection Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
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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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
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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
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/312—Non-condensed aromatic systems, e.g. benzene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
- C08G2261/3142—Condensed aromatic systems, e.g. perylene, anthracene or pyrene fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/37—Metal complexes
- C08G2261/374—Metal complexes of Os, Ir, Pt, Ru, Rh, Pd
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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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- C—CHEMISTRY; METALLURGY
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Description
Mは、各々の出現について同一であるか異なり、原子番号>38を有する主族金属、遷移金属またはランタノイドであり、
DCyは、各々の出現について同一であるか異なり、少なくとも1つのドナー原子、すなわち、自由電子対を有する原子、好ましくは窒素またはリン(これを介して環状基は金属に結合する)を含有し、且つ1個以上の置換基R1を有していてもよい環状基であり、基DCyおよびCCyは、共有結合により互いに結合し、また基R1およびR2により互いにさらなる結合を有していてもよく、
CCyは、各々の出現について同一であるか異なり、炭素原子(これを介して環状基は金属に結合する)を含有し、且つ1個以上の置換基R1を有していてもよい環状基であり、
Lは、各々の出現について同一であるか異なり、二座配位子、好ましくはモノアニオン性の二座キレート配位子であり、
R1は、各々の出現について同一であるか異なり、H、F、Cl、Br、I、NO2、CN、1〜40個のC原子を有する直鎖の、分枝の若しくは環状のアルキル基若しくはアルコキシ基(ここで、1個以上の非隣接のCH2基は、C=O、C=S、C=Se、C=NR2、−R2C=CR2−、−C≡C−、−O−、−S−、−NR2−、Si(R2)2、または−CONR2−により置き換えられていてもよく、且つ1個以上のH原子は、F、Cl、Br、I、CN、NO2により置き換えられていてもよい)、または5〜40個の芳香族環原子を有する芳香族環系若しくは複素環式芳香族環系(これらは、1個以上の非芳香族基R1により置き換えられてもよい)であり、ここで同じ環上、また2つの異なる環上の複数の置換基R1は、さらなる単環または多環の脂肪族環系または芳香族環系を互いに形成していてもよく、
R2は、各々の出現について同一であるか異なり、H、または1〜20個のC原子を有する脂肪族炭化水素基または芳香族炭化水素基であり、
mは、各々の出現について、1、2または3であり、好ましくは2または3であり、特に好ましくは3であり、
nは、各々の出現について、0、1または2であり、好ましくは0または1であり、特に好ましくは0である)。
例1:イリジウム化合物の合成
a)トリス(3−ブロモフェニルイソキノリン)イリジウム(Ir1)の合成
モノマーIr1の合成は、WO 02/068435 に記載される通りに、トリス(フェニルイソキノリン)イリジウム(III)の臭素化により行った。
モノマーIr2およびIr3の合成を、未公開出願 DE 10350606.3 に記載される通りに行った。
可溶な変形例であるイリジウム錯体(Ir4)を、モノマーIr1から、WO 04/026886 に記載されているスズキカップリングにより得た。
用いられるさらなるコモノマーおよび単官能化合物の合成は、WO 02/077060 およびここに挙げられる文献に詳細に記載されている。以下で用いたコモノマーM1〜M7を、明瞭にするためにここで再び示すs。
ポリマーを、WO 03/048225 に一般に記載されるように、スズキカップリングにより合成した。合成したポリマーP1〜P5(例5〜9)の組成と、比較ポリマーまたは比較ブレンドC1〜C3(例10〜13)を、その物性と共に表1に示す。
PLEDを製造することができる方法は、WO 04/037887 とここに挙げられる文献に詳細に記載されている。
調製した全てのポリマーを、PLEDにおいて詳しく調べた。ポリマーの組成とエレクトロルミネセンスの結果を、表1に示す。用いた比較例は、イリジウム錯体のジブロモ誘導体(Ir2およびIr3)を用いて得られる線状(非分枝)ポリマーである。また、比較例として用いたのは、金属錯体を含まないポリマーと、可溶な変形例であるイリジウム錯体(Ir4)およびトリブロム化イリジウムモノマー(Ir1)とのブレンドである。
a モノマーの割合はモル%であり、ポリマー中に存在する全ての繰り返し単位に基づく
b CIE座標:the Commission Internationale de l'Eclairage from 1931 の色度座標
c 寿命は、発光ダイオードの光束密度が、10mA/cm2の電流密度において、初期の光束密度の半分にまで低下した時間として定義される
d 寿命を、10mA/cm2の電流密度で測定せず、代わりに800cd/m2の初期輝度で測定した。
Claims (14)
- −0.05〜10モル%の少なくとも一つの三重項エミッタおよび
−ポリマー骨格を形成するさらなる構造要素を含むリン光コポリマーであって、
−前記三重項エミッタが、式(1)の構造を有することを特徴とし、
Mは、各々の出現について同一であるか異なり、イリジウム又は白金であり、
DCyは、各々の出現について同一であるか異なり、少なくとも1つのドナー原子(これらを介して環状基は金属に結合する)を含有し、且つ1個以上の置換基R1を有していてもよい環状基であり、基DCyおよびCCyは、共有結合により互いに結合し、また基R1およびR2により互いにさらなる結合を有していてもよく、
CCyは、各々の出現について同一であるか異なり、炭素原子(これを介して環状基は金属に結合する)を含有し、且つ1個以上の置換基R1を有していてもよい環状基であり、
Lは、各々の出現について同一であるか異なり、二座配位子であり、
R1は、各々の出現について同一であるか異なり、H、F、Cl、Br、I、NO2、CN、1〜40個のC原子を有する直鎖の、分枝の若しくは環状のアルキル基若しくはアルコキシ基(ここで、1個以上の非隣接のCH2基は、C=O、C=S、C=Se、C=NR2、−R2C=CR2−、−C≡C−、−O−、−S−、−NR2−、Si(R2)2、または−CONR2−により置き換えられていてもよく、且つ1個以上のH原子は、F、Cl、Br、I、CN、NO2により置き換えられていてもよい)、または5〜40個の芳香族環原子を有する芳香族環系若しくは複素環式芳香族環系(これらは、1個以上の非芳香族基R1により置き換えられていてもよい)であり、ここで同じ環上、また2つの異なる環上の複数の置換基R1は、さらなる単環または多環の脂肪族環系または芳香族環系を互いに形成していてもよく、
R2は、各々の出現について同一であるか異なり、H、または1〜20個のC原子を有する脂肪族炭化水素基または芳香族炭化水素基であり、
mは、各々の出現について、1、2または3であり、
nは、各々の出現について、0、1または2である)、
−前記三重項エミッタは、前記ポリマーへの少なくとも3つの結合を有することを特徴とし、
−前記さらなる構造要素は、ポリマー骨格を形成し、フルオレン誘導体、スピロビフルオレン誘導体、9,10−ジヒドロフェナントレン誘導体、4,5−ジヒドロピレン誘導体、4,5,9,10−テトラヒドロピレン誘導体、フェナントレン誘導体、並びにシス−およびトランス−インデノフルオレン誘導体から選択され、但し、前記三重項エミッタが無置換のトリス(フェニルピリジン)イリジウム(III)である場合には、前記ポリマーは、9,9−ジオクチルフルオレンを含まないことを特徴とする、
リン光コポリマー。 - 正孔輸送性を有し、トリアリールアミン誘導体、ベンジジン誘導体、テトラアリーレン−パラ−フェニレンジアミン誘導体、トリアリールホスフィン誘導体、フェノチアジン誘導体、フェノキサジン誘導体、ジヒドロフェナジン誘導体、チアントレン誘導体、ジベンゾ−p−ジオキシン誘導体、フェノキサチイン誘導体、カルバゾール誘導体、アズレン誘導体、チオフェン誘導体、ピロール誘導体、フラン誘導体、および高いHOMOを有する他のO−、S−またはN−含有複素環の群から選択されるさらなる構造要素を含むことを特徴とする請求項2記載のリン光コポリマー。
- 電子輸送性を有し、ピリジン誘導体、ピリミジン誘導体、ピリダジン誘導体、ピラジン誘導体、アントラセン誘導体、ピレン誘導体、トリアリールボラン誘導体、オキサジアゾール誘導体、キノリン誘導体、キノキサリン誘導体、フェナジン誘導体、および低いLUMOを有する他のO−、S−またはN−含有複素環の群から選択されるさらなる構造要素を含むことを特徴とする請求項1または2記載のリン光コポリマー。
- 一重項状態から三重項状態への遷移を改善し、カルバゾール、ケトン、ホスフィンオキシド、スルホキシド、およびアリールシランの群から選択されるさらなる構造要素を含むことを特徴とする請求項2または3記載のリン光コポリマー。
- 芳香族ケトンおよび芳香族ホスフィンオキシドから選択されるさらなる構造要素を含むことを特徴とする請求項4に記載のリン光コポリマー。
- モノマーとして、相応して三官能化された三重項エミッタを組み込むことにより得られることを特徴とする請求項1〜5いずれか一項記載のリン光コポリマー。
- 前記三重項エミッタが、キレート配位子のみを含むことを特徴とする請求項1〜6いずれか一項記載のリン光コポリマー。
- 添え字m=2または3であり、添え字n=0であることを特徴とする請求項7に記載のリン光コポリマー。
- 前記ポリマーへの結合が、少なくとも3つの配位子により行われることを特徴とする請求項1〜8いずれか一項記載のリン光コポリマー。
- 請求項1〜9いずれか一項記載の1種以上のコポリマーと、1種以上の共役した、部分的に共役した、または非共役のポリマー、オリゴマー、デンドリマー、または低分子量化合物とのブレンド。
- 1種以上の溶媒中の、請求項1〜10いずれか一項記載の1種以上のコポリマーまたはブレンドの溶液または調合物。
- 有機電子デバイスにおける、請求項1〜11いずれか一項記載のコポリマーまたはブレンドまたは溶液の使用。
- 1つ以上の層を有する有機電子デバイスであって、これらの層の少なくとも1つが、請求項1〜10いずれか一項記載の少なくとも1種のコポリマーまたはブレンドを含む有機電子デバイス。
- 有機若しくはポリマー発光ダイオード、有機太陽電池、非線形光学素子、有機光学検波器、有機電界クエンチデバイス(organic field-quench device)、または有機レーザダイオードであることを特徴とする請求項13に記載の有機電子デバイス。
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- 2005-07-06 JP JP2007519714A patent/JP5442200B2/ja active Active
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JP2008505239A (ja) | 2008-02-21 |
US20070281182A1 (en) | 2007-12-06 |
CN1997722A (zh) | 2007-07-11 |
EP1763566B1 (de) | 2016-10-26 |
KR101206313B1 (ko) | 2012-11-29 |
EP1763566A1 (de) | 2007-03-21 |
WO2006003000A1 (de) | 2006-01-12 |
TW200617141A (en) | 2006-06-01 |
US7820305B2 (en) | 2010-10-26 |
KR20070033416A (ko) | 2007-03-26 |
DE102004032527A1 (de) | 2006-02-02 |
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