CN101489961B - 电致发光聚合物及其用途 - Google Patents
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- CN101489961B CN101489961B CN200780026014.9A CN200780026014A CN101489961B CN 101489961 B CN101489961 B CN 101489961B CN 200780026014 A CN200780026014 A CN 200780026014A CN 101489961 B CN101489961 B CN 101489961B
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- 229920000642 polymer Polymers 0.000 title claims abstract description 24
- 239000000126 substance Substances 0.000 claims description 90
- 125000004432 carbon atom Chemical group C* 0.000 claims description 58
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 150000003254 radicals Chemical class 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 239000003205 fragrance Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 238000002347 injection Methods 0.000 claims description 11
- 239000007924 injection Substances 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- 238000000576 coating method Methods 0.000 claims description 9
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 230000021615 conjugation Effects 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- -1 phosphine oxide, sulfoxide Chemical class 0.000 claims description 6
- 230000007704 transition Effects 0.000 claims description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 238000004020 luminiscence type Methods 0.000 claims description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 3
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical compound C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 claims description 3
- 230000008859 change Effects 0.000 claims description 3
- 125000005259 triarylamine group Chemical group 0.000 claims description 3
- ZIZMDHZLHJBNSQ-UHFFFAOYSA-N 1,2-dihydrophenazine Chemical compound C1=CC=C2N=C(C=CCC3)C3=NC2=C1 ZIZMDHZLHJBNSQ-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 2
- 238000006471 dimerization reaction Methods 0.000 claims description 2
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- 229910052741 iridium Inorganic materials 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003233 pyrroles Chemical class 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 235000021286 stilbenes Nutrition 0.000 claims description 2
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 150000003457 sulfones Chemical class 0.000 claims 1
- 239000000178 monomer Substances 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 4
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 239000011532 electronic conductor Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 229920000265 Polyparaphenylene Polymers 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229920001059 synthetic polymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
- WPCIUCNVWJNRCD-UHFFFAOYSA-N 4,5-dihydropyrene Chemical class C1=CC=C2CCC3=CC=CC4=CC=C1C2=C34 WPCIUCNVWJNRCD-UHFFFAOYSA-N 0.000 description 1
- DOJFBBMXBZGEAG-UHFFFAOYSA-N 5,6-dibromobenzo[a]phenalen-7-one Chemical compound Brc1cc2cccc3-c4ccccc4C(=O)c(c1Br)c23 DOJFBBMXBZGEAG-UHFFFAOYSA-N 0.000 description 1
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical compound C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 description 1
- XXPBFNVKTVJZKF-UHFFFAOYSA-N 9,10-dihydrophenanthrene Chemical class C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 1
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical class C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 description 1
- WVQCISGJPQZUQM-UHFFFAOYSA-N BrC1=CC=C2C=CC=C3C(C=4C=CC=CC4C1=C23)(C)C Chemical compound BrC1=CC=C2C=CC=C3C(C=4C=CC=CC4C1=C23)(C)C WVQCISGJPQZUQM-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- 238000006619 Stille reaction Methods 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000005264 aryl amine group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 150000004646 arylidenes Chemical group 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
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- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 235000021384 green leafy vegetables Nutrition 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910000474 mercury oxide Inorganic materials 0.000 description 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229920001690 polydopamine Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000003245 working effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/269—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of only halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
-
- 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
- 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
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- 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
- C08G61/121—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from organic halides
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- 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
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
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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
- 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
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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Abstract
本发明涉及包含通式(1)结构单元的电致发光聚合物及其用途。根据本发明的聚合物显示了改进的效率和更长的寿命,特别是当用于聚合物有机发光二极管时。
Description
本发明涉及包含通式(1)结构单元的电致发光聚合物及其用途。根据本发明的聚合物显示改进的效率和更长的寿命,特别是当用于聚合有机发光二极管时。
对基于聚合(有机)发光二极管(PLEDs)的显示和照明元件广泛的商业化研究已经开展了10年多了。该开发是由公开在WO90/13148 A1中的基础开发引发的。首先,虽然简单,但产品(PHILIPSN.V.剃须刀中小的显示器)最近也已经能在市场上获得。然而,使用材料的显著改进仍是必要的,以使这些显示器成为目前主宰市场的液晶显示器(LCDs)的真正竞争者。
为了制造所有三种发光颜色,有必要将某些共聚单体共聚到相应的聚合物中(参见,例如WO 00/046321 A1,WO 03/020790 A2和WO 02/077060 A1)。以这种方法,从发蓝色光基础聚合物(“骨架”)开始,然后通常有可能生产其他两种原色红色和绿色。
已经提出或开发的用于全色显示元件的聚合物是各种种类的材料。因此,例如聚芴衍生物以及聚螺二芴、聚二氢菲和聚茚并芴的衍生物都是适当的。还已经提出了包括所述结构要素的组合的聚合物。另外,目前使用包含聚对亚苯(PPP)作为结构要素的聚合物。
根据现有技术的聚合物在某些情况下用于PLEDs中时已经显示出良好的性能。然而,尽管已经实现了进展,但这些聚合物还不能满足使它们用于高性能应用的要求。
特别是,发绿色,尤其是发蓝色光聚合物的寿命对于许多应用仍不够。这同样适用于发红光聚合物的情况。
令人惊讶地,现在发现一种新颖种类的聚合物具有优于上述现有技术的良好性能。 因此本发明涉及这些聚合物及其在PLEDs中的用途。该新颖的结构单元特别适宜作为聚合物骨架,但取决于取代型式,也可以作为空穴导体、电子导体和/或发光体。
本发明涉及包含通式(1)单元的聚合物,
通式(1)
其中
R每一次出现相同或不同,是H,具有1~40个碳原子的直链烷基链、具有3~40个碳原子的支化烷基链或具有3~40个碳原子的环状烷基链,它们每一个可被R1取代,以及其中另外一个或多个非相邻的碳原子可以被=N-R1、-O-、-S-、-O-CO-O-、-CO-O-、-CR1=CR1-或-C≡C-替代,以及其中另外一个或多个H原子可以被F、Cl、Br、I或CN替代,或者具有5~40个碳原子的芳香环系或具有2~40个碳原子的杂芳环系,它们可被一个或多个基团R1取代;此处两个基团R也可以彼此形成其他的单或多环的芳香或脂肪环系;优选条件是至少一个或两个基团R不等于H;
R1每一次出现相同或不同,是H,具有1~22个碳原子的直链烷基链、具有3~22个碳原子的支化烷基链或具有3~22个碳原子的环状烷基链,其中另外一个或多个非相邻的碳原子可以被=N-R2、-O-、-S-、-O-CO-O-、-CO-O-、-CR2=CR2-或-C≡C-替代,以及其中另外一个或多个H原子可以被F、Cl、Br、I或者CN替代,或者具有5~40个碳原子的芳基、杂芳基、芳氧基或者杂芳氧基基团,它们还可以被一个或多个非芳基R1取代;此处两个或多个基团R1彼此和/或与R也可以形成环系;或者是F、Cl、Br、I、CN、N(R2)2、Si(R2)3或B(R2)2;
R2每一次出现相同或不同,是H或者具有1~20个碳原子的脂肪或者芳香烃基团;
X每一次出现相同或不同,是B、C、N、O、P、S、Se、P=O、S=O或SO2;
n每一次出现相同或不同,是0、1、2或3;
m每一次出现相同或不同,是0、1或2;并且
在通式(1)和在所有其他通式中的虚线键表示聚合物中的链接。此处它不意欲代表甲基。
本发明优选涉及包含通式(1a)单元的聚合物,
通式(1a)
其中
R每一次出现相同或不同,是H,具有1~40个碳原子的直链烷基链、具有3~40个碳原子的支化烷基链或具有3~40个碳原子的环状烷基链,它们每一个可被R1取代,以及其中另外一个或多个非相邻的碳原子可以被=N-R1、-O-、-S-、-O-CO-O-、-CO-O-、-CR1=CR1-或-C≡C-替代,以及其中另外一个或多个H原子可以被F、Cl、Br、I或CN替代,或者具有5~40个碳原子的芳香环系或具有2~40个碳原子的杂芳环系,它们可被一个或多个基团R1取代;此处两个基团R也可以彼此形成其他的单或多环的芳香或脂肪环系;优选条件是至少一个或两个基团R不等于H;
R1每一次出现相同或不同,是H,具有1~22个碳原子的直链烷基链、具有3~22个碳原子的支化烷基链或具有3~22个碳原子的环状烷基链,其中另外一个或多个非相邻的碳原子可以被=N-R2、-O-、-S-、-O-CO-O-、-CO-O-、-CR2=CR2-或-C≡C-替代,以及其中另外一个或多个H原子可以被F、Cl、Br、I或者CN替代,或者具有5~40个碳原子的芳基、杂芳基、芳氧基或者杂芳氧基基团,它们还可以被一个或多个非芳基R1取代;此处两个或多个基团R1彼此和/或与R也可以形成环系;或者是F、Cl、Br、I、CN、N(R2)2、Si(R2)3或B(R2)2;
R2每一次出现相同或不同,是H或者具有1~20个碳原子的脂肪或者芳香烃基团;
X每一次出现相同或不同,是B、C、N、O、P、S、Se、P=O、S=O或SO2;
G每一次出现相同或不同,代表选自第1组、第2组、第3组、第4组、第5组、第6组、第7组或第1~7组多种混合的二价单元。
n每一次出现相同或不同,是0、1、2或3;
m每一次出现相同或不同,是0、1或者2;
p每一次出现相同或不同,是0或1;并且
在通式(1a)和在所有其他通式中的虚线键表示聚合物中的链接;此处它不意欲代表甲基。
尽管这从描述中显而易见,但应该再一次明确地指出此处通式(1)和(1a)的结构单元可以是非对称的取代,即在一个单元上可存在不同的取代基R或R1。
为了本发明的目的,芳香或杂芳环系确定为意思是没有必要分别仅包含芳香或者杂芳基团的体系,而是其中多个芳香或杂芳基团也可以被短的非芳香单元(<10%的非H原子,优选<5%的非H原子)间断,比如sp3-杂化的C、O、N等。因此,比如9,9′-螺二芴,9,9-二芳基芴,三芳基胺等体系,在本发明的应用中也确定为意思是芳香环系。
根据本发明的聚合物通常包含至少5mol%,优选至少10mol,特别优选至少30mol%,特别是至少50mol%的通式(1)或(1a)的单元。已经发现:如果同时存在不同的通式(1)或(1a)的单元,则通式(1)和(1a)所有单元的总和在上述范围内,使得通式(1)和(1a)的单个单元的含量在此情况下也可以小于5mol%。
根据本发明的聚合物是共轭或部分共轭的聚合物。
为了本发明的目的,共轭聚合物是这样的聚合物:在主链中主要包含sp2-杂化的碳原子,所述碳原子也可以被相应的杂原子替代。在最简单的情况下,其意味着在主链上交替存在双和单键。“主要”意思是导致共轭中断的天然缺陷不会使术语“共轭聚合物”无效。而且,如果例如芳基胺单元和/或某些杂环化合物(即经由N、O或S原子共轭)和/或有机金属络合物(即经由金属原子共轭)位于主链中,在此情况下术语共轭同样适用。
相反,单元,比如简单的烷基桥联、(硫)醚、酯、酰胺或酰亚胺链接,清楚地定义为非共轭链段。部分共轭的聚合物确定为意思是其中在主链中延伸的共轭链段被非共轭链段间断的聚合物,或者其中在主链中是非共轭的而在侧链中包含延伸的共轭链段的聚合物。
除通式(1)或(1a)的单元以外,根据本发明的聚合物也可以包含其他结构要素。这些尤其是在WO 02/077060 A1和DE 10337346 A1中公开并大量列出的那些。这些通过参考的方式作为本发明的一部分。其他的结构单元例如可以源自以下种类:
第1组:提高聚合物的空穴注入和/或传导特性的单元;
第2组:提高聚合物的电子注入和/或传输特性的单元;
第3组:具有第一组和第二组单个单元组合的单元;
第4组:改善发光特性达到这样的程度使得能获得电致磷光而非电致发光的单元;
第5组:改善从所谓的单重态到三重态跃迁的单元;
第6组:影响得到的聚合物形态和/或发光色彩的单元;
第7组:通常用作骨架的单元。
根据本发明优选的聚合物是其中至少一个结构要素具有电荷传输特性的那些,即包含源自第1和/或第2组单元的那些。
源自第1组的结构要素具有空穴传输特性,例如是三芳基胺、联苯胺、四芳基对苯二胺、三芳基膦、吩噻嗪、吩噁嗪、二氢吩嗪、噻蒽、二苯并对二噁英、吩噁噻、咔唑、薁、噻吩、吡咯和呋喃衍生物,和其他具有高HOMO(HOMO=最高占据分子轨道)的含O、S或者N的杂环。这些芳基胺和杂环优选导致聚合物中的HOMO大于-5.8ev(相对真空能级),特别优选大于-5.5ev。
源自第2组的结构要素具有电子传输特性,例如是吡啶、嘧啶、哒嗪、吡嗪、噁二唑、喹啉、喹喔啉和吩嗪衍生物,以及三芳基硼烷和其他具有低LUMO(LUMO=最低未占分子轨道)的含O、S或者N的杂环化合物。这些聚合物中的单元优选导致LUMO小于-2.7ev(相对真空能级),特别优选小于-3.0ev。
优选根据本发明的聚合物包含源自第3组的单元,其中增加空穴迁移率的结构和增加电子迁移率的结构(即源自第1和第2组的单元)彼此直接结合。这些单元的一些可以作为发光体并使发光颜色改变为绿色、黄色或红色。它们的用途因此例如适合用于由最初的发蓝色光聚合物制造其他的发光颜色。
第4组的结构要素是能够甚至在室温下自三重态高效率地发光的那些,即显示电致磷光而不是电致发光,这通常引起能量效率的提高。首先适合于该目的是包括原子序数大于36的重原子的化合物。优选包含满足上述条件的d或f过渡金属的化合物。此处特别优选包括第8~10族元素(Ru、Os、Rh、Ir、Pd、Pt)的相应结构单元。此处用于根据本发明的聚合物的适合结构单元例如是各种络合物,例如描述在WO02/068435 A1、DE 10116962 A1、EP 1239526 A2和DE 10238903 A1中。相应的单体描述在WO 02/068435 A1和DE 10350606 A1中。
源自第5组的结构要素是可以改善从单线态到三线态跃迁的那些,可用于支撑第4组的结构要素,改善这些结构要素的磷光特性。适合于该目的特别是咔唑和桥联咔唑二聚单元,如在DE 10304819 A1和DE 10328627 A1中所描述的。还适合于该目的的是酮、氧化膦、亚砜等化合物,如在DE 10349033中描述的。
源自第6组的结构要素影响聚合物的形态和/或发光颜色,除如上所述的那些外,是具有至少一个别的芳香或者其他共轭结构但不属于上述组的那些,即,对电荷载流子迁移率仅有很小影响,不是有机金属络合物或者对单线态-三重态跃迁没有影响的那些。该类型的结构要素影响得到的聚合物的形态和/或发光颜色。取决于所述单元,因此它们还可以用作发光体。此处优选具有6~40个碳原子的芳香结构,或者二苯乙炔、二苯乙烯或二苯乙烯基亚芳基的衍生物,它们每个可被一个或多个基团R1取代。此处特别优选并入1,4-亚苯基、1,4-亚萘基、1,4-或9,10-亚蒽基、1,6-、2,7-或4,9-亚芘基、3,9-或3,10-亚二萘嵌苯、4,4′-亚联苯基、4,4″-亚三联苯基、4,4′-亚-1,1′-联萘基、4,4′-亚二苯乙炔基、4,4′-亚芪基或4,4″-二苯乙烯基亚芳基衍生物。
源自第7组的结构要素是通常用作聚合物骨架的、包括具有6~40个碳原子芳香结构的单元。这些例如是4,5-二氢芘衍生物、4,5,9,10-四氢芘衍生物、芴衍生物、9,9’-螺二芴衍生物、9,10-二氢菲衍生物、5,7-二氢二苯并氧杂衍生物,以及顺式的和反式的茚并芴衍生物。然而,通式(1)或(1a)单元的比例,特别为至少50mol%,此处这些源自第7组的结构要素不优选用作主要的聚合物骨架,而是最多以较小比例存在于骨架中。
根据本发明优选的聚合物,除通式(1)或(1a)的结构单元之外,同时另外还包括一种以上选自第1~7组的单元。同样优选同时存在源自一组的多于一种的结构单元。
通式(1)或(1a)单元的比例优选至少为10mol%,特别优选至少为30mol%,和特别是至少为50mol%。如果通式(1)或(1a)的单元是聚合物骨架,该优选特别适用。在其他功能情况下,其他比例可以是优选的,例如在电致发光聚合物中空穴导体或发光体的情况下,比例约为5~20mol%。为了其它的应用,例如用于有机晶体管,所述优选的比例也可以不同,例如在空穴或者电子传导单元的情况下,可高达100mol%。
根据本发明的聚合物,优选除通式(1)或(1a)的结构单元之外,还包含至少一种源自上述组类的结构单元。至少两种结构单元特别优选源自上述那些的不同种类。如果存在,这些结构单元的比例在每一情况下优选至少为5mol%,在每一情况下特别优选为至少10mol%。特别地,这些结构单元之一选自空穴传导单元的组和其他发光单元的组,其中这两种功能(空穴传导和发光)也可以由相同的单元承担。
然而,例如为了合成白色发光共聚物,发光单元,特别是绿色和红色发光单元的较小比例也可以是优选的。合成发白色光共聚物的方法详细地描述在DE 10343606 A1中。
本发明的聚合物优选具有10~10,000,特别优选50~5000,特别是50~2000个重复单元。
尤其通过在通式(1)或(1a)单元上,以及任选在其他存在的单元上的取代基R和R1,保证聚合物需要的溶解度。如果存在其他的取代基,这些取代基也可以促进溶解度。
为保证足够的溶解度,优选平均在每个重复单元的取代基中存在至少2个非芳香C原子。此处优选至少4个,特别优选至少8个C原子。其单个碳原子也可以被O或S替代。然而,对于此完全有可能意味着某些比例的重复单元不载带任何其他的非芳香取代基。
为避免损害膜的形态,优选在线性链中没有多于12个C原子的长链取代基,特别优选没有多于8个C原子,特别是没有多于6个C原子的长链取代基。
非芳香C原子例如象在通式(1)或(1a)的R和R1的描述中,存在于相应的直链、支化或者环状的烷基或者烷氧基链中。
优选根据本发明的聚合物,其中对于通式(1)或(1a)的单元,
R每一次出现相同或不同,表示具有1~25个碳原子的直链烷基链、具有3~25个碳原子的支化烷基链或具有3~25个碳原子的环状烷基链,其中另外一个或多个非相邻的碳原子可以被=N-R1、-O-、-S-、-O-CO-O-、-CO-O-、-CH=CH-或-C≡C-取代,以及其中另外一个或多个H原子可以被F或CN替代,或者具有5~20个碳原子的芳香环系或具有2~20个碳原子的杂芳环系,它们可被一个或多个非芳基R1取代;此处两个基团R也可以彼此形成其他的单或多环的芳香或脂肪环系;
R1每一次出现相同或不同,表示H,具有1~22个碳原子的直链烷基链、具有3~22个碳原子的支化烷基链或具有3~22个碳原子的环状烷基链,其中另外一个或多个非相邻的碳原子可以被=N-R2、-O-、-S-、-O-CO-O-、-CO-O-、-CH=CH-或-C≡C-替代,以及其中另外一个或多个H原子可以被F或CN替代,或者具有5~40个碳原子的芳基、杂芳基、芳氧基或杂芳氧基基团,它们还可以被一个或多个非芳基R1取代;此处两个或多个基团R1彼此和/或与R也可以形成单或多环的脂肪或芳香环系;或者是F、Cl、Br、I、CN、N(R2)2、Si(R2)3或B(R2)2;并且
X每一次出现相同或不同,是B、C、N、O、P、S、P=O、S=O或SO2。
优选根据本发明的聚合物,其中对于通式(1)或(1a)的单元,
R每一次出现相同或不同,是具有4~20个碳原子的直链、支化或环状烷基链,特别优选支化烷基链,其中另外一个或多个非相邻的碳原子可以被=N-R1、-O-、-S-、-O-CO-O-、-CO-O-、-CH=CH-或-C≡C-替代,其中另外一个或多个H原子可以被F替代;此处两个基团R也可以彼此形成其他的单或多环环系;
X每一次出现是C;并且
p代表数字0。
脂肪烃基R的优选能这样解释:得到的聚合物还有更好的溶解性和更好的合成可得性。
取决于取代模式,通式(1)或(1a)的单元特别适合于聚合物中的各种功能。因此,这些单元可以优选用作(电子传导)聚合物骨架、作为空穴导体或作为发光体。
而且优选在7,7′-位对称取代的通式(1)或(1a)的单元。该优选能通过该单体更好的合成可得性来解释。因此,对于通式(1)或(1a)单元中所有的R优选是相同的,特别优选还被相同地取代。
通式(1)或(1a)优选单元的实例是以下的结构,其中在每一情况下在聚合物中的链接如虚线键所示经由3,9-位发生。为清楚起见,可能的取代基通常未示出或不是在每个地方都示出。如对于R的描述,此处烷基通常代表脂肪烷基,芳基代表芳香或杂芳族体系。
根据本发明的聚合物或者是均聚物或者是共聚物。除了通式(1)或(1a)的一个或多个结构,根据本发明的共聚物可以任选包括一个或多个其他的结构,例如上述第1~7组中的那些。
根据本发明的共聚物可以具有无规的、交替的或者嵌段状结构,或者还具有交替排列的多个这些结构。能获得具有嵌段状结构共聚物的方法例如详细地描述于DE 10337077 A1中。该未审公开的说明书以参考的方式成为本申请的一部分。
通过使用多种不同的结构要素能够调节这些性能比如:溶解性、固相形态、颜色、电荷注入和传输特性、温度稳定性、电光特性等等。
根据本发明的聚合物通常通过聚合一种或多种类型的单体制备,其中至少一种单体得到所述聚合物通式(1)或(1a)的单元。原则上有许多对应的聚合反应。然而,这里得到C-C或C-N链接的一些类型被证明是特别成功的:
(A)SUZUKI聚合;
(B)YAMAMOTO聚合;
(C)STILLE聚合;
(D)HARTWIG-BUCHWALD聚合。
可以通过这些方法进行聚合的方式,以及可以从反应介质分离聚合物并纯化的方式详细地描述在例如DE 10249723 A1中。
得到根据本发明聚合物中通式(1)结构单元的单体是在3,9-位具有适当官能团,使得该单体单元能并入聚合物中的衍生物。如果希望另外的链接,则必须相应地改变官能团。
得到该聚合物中通式(1)或(1a)单元的单体是新颖的,因此同样是本发明的主题。
因此,本发明进一步涉及通式(2)或(2a)的双官能单体化合物。
通式(2)
通式(2a)
其特征在于两个官能团A相同或不同,并在C-C或C-N链接反应条件下共聚,其中其他符号和标记具有与通式(1)或(1a)相同的含义。
A优选选自Cl,Br,I,O-甲苯磺酸酯,O-三氟甲磺酸酯,O-SO2R2,B(OR2)2和Sn(R2)3,特别优选选自Br,I和B(OR2)2,其中R2具有如上所述相同的含义,其中两个或多个基团R2也可以彼此形成环系。
所述C-C链接反应优选选自SUZUKI偶联,YAMAMOTO偶联和STILLE偶联;所述C-N链接反应优选为HARTWIG-BUCHWALD偶联。
如上所述对于通式(1)或(1a)结构单元相同的优选适用于通式(2)或(2a)的双官能单体化合物。
优选不使用根据本发明的聚合物作为纯物质,而是作为与任何期望的其他聚合的、低聚的、树枝状的或低分子量的物质一起的混合物(共混物)。这些例如可以改进电子性能,影响从单重态到三重态的跃迁或它们本身从单重态或从三重态的发光。然而,电子惰性的物质也可以是适当的,例如为了影响形成的聚合物膜的形态或聚合物溶液的粘度。因此本发明还涉及该类型的共混物。
本发明还涉及根据本发明的一种或多种聚合物或共混物在一种或多种溶剂中的溶液和制剂。能够制备聚合物溶液的方式例如描述在WO 02/072714 A1、WO 03/019694 A2和在其中引用的文献中。这些溶液可用于生产薄的聚合物层,例如通过表面涂覆方法(例如旋涂)或者印刷工艺(例如喷墨印刷)。
根据本发明的聚合物能用在PLEDs中。这些包括阴极、阳极、发光层和任选的其他层,比如优选空穴注入层和任选在空穴注入层与发光层之间的中间层。能生产PLEDs的方法,作为通常的方法详细地描述在DE 10304819 A1中,其应该相应地适应于个别的情况。
如上所述的,根据本发明的聚合物非常特别适合作为以该方式生产的PLEDs或者显示器中的电致发光材料。
为了本发明的目的,电致发光材料被认为是指能用作PLED中的活性层的材料。活性层意思是在施加电场时发光的层(发光层)和/或改进正和/或负电荷注入和/或传输的层(电荷注入或电荷传输层)。它还可以是在空穴注入层与发光层之间的中间层。
因此本发明还涉及根据本发明的聚合物在PLED中的用途,特别是作为电致发光材料的用途。
因此,本发明同样涉及具有一个或多个活性层的PLED,其中至少这些活性层之一包括一种或多种根据本发明的聚合物。该活性层例如可以是发光层和/或传输层和/或电荷注入层和/或中间层。
根据本发明的聚合物具有以下令人惊讶的优点,超过了在此作为最接近现有技术的WO 03/020790 A2和WO 02/077060 A1中描述的聚螺二芴和聚芴:
(1)已经发现根据本发明的聚合物(以及其他相同或类似的组合物)在应用中具有更高的发光效率。这特别适用于显示蓝色发光的共聚物。这是非常重要的,因为这样可以在较低能量消耗下实现相同的亮度,这特别是在依赖标准或可充电电池的移动应用(移动电话、传呼机、PDAs的显示器等等)中是非常重要的。相反,用相同的能量消耗可以获得更高的亮度,这例如对于照明应用是吸引人的。
(2)此外在直接比较中再次令人惊讶地发现,根据本发明的聚合物具有更长的使用寿命,特别是在发绿色和发蓝色光的PLEDs的情况下。
(3)即使不使用电子传导的共聚单体,根据本发明的聚合物也是良好的电子导体。因为根据现有技术的许多电子导体对于高性能应用不够稳定,因而至今难以实现聚合物的电子传导性能。
本发明申请文本以及以下的实施例涉及根据本发明的聚合物或共混物在PLEDs和相应显示器中的用途。尽管描述是有限的,但对于本领域普通技术人员而言,不需要其他创造性劳动,同样可以将根据本发明的聚合物使用于在其他电子器件中的其它用途,该其他电子器件例如仅提及一些应用:有机集成电路(O-ICs)、有机场效应晶体管(OFETs)、有机薄膜晶体管(OTFTs)、有机太阳能电池(O-SCs)或有机激光二极管(O-lasers)。
本申请同样涉及根据本发明的聚合物在相应器件中的用途和这些器件本身。
以下更详细地参考实施例更加详细地阐明本发明,但并不限制于此。
实施例:
实施例1:制备3,9-二溴-7,7-二甲基-7H-苯并[de]蒽
1.1制备3,9-二溴苯并[de]蒽-7-酮
将50g(217mmol)的苯并蒽酮首先引入800ml的硝基苯中,使内部温度达到90℃。在30分钟之内逐滴加入溶解在100ml硝基苯中的25ml(490mmol)的溴。然后该反应混合物被加热到150℃的内部温度。在2小时之后,将该混合物冷却到室温,逐滴加入200ml的EtOH,用抽滤出黄色沉淀,用大量的EtOH洗涤,干燥,得到49.7g(59%)作为黄色粉末的二溴化产物。
1.2制备3,9-二溴-7H-苯并[de]蒽
将37.17g(81.7mmol)的二溴苯并蒽酮和10.9g(81.7mmol)的AlCl3在N2下首先引入已经通过加热干燥的设备中的330ml干燥的乙醚中。然后在冰冷却下逐滴加入在400ml醚中的3.1g(81.7mmol)LiAlH4(预先在冰冷却、N2下溶解或悬浮)。当加入完成时,将该混合物加热至沸腾另外的60分钟。
在冰冷却情况下缓慢加入10ml的乙酸乙酯,随后小心地逐滴加入100ml的6M HCl,用抽滤出得到的沉淀,用1M的HCl和甲醇洗涤,通过抽吸干燥,得到25.6g(84%)的淡黄色固体。
1.3制备3,9-二溴-7,7-二甲基-7H-苯并[de]蒽
将26g(69mmol)的3,9-二溴-7H-苯并[de]蒽于70℃下溶解在280ml干燥的DMSO中,加入40g(416mmol)的NaOtBu,加热该悬浮体到80℃的内部温度。在该温度下缓慢逐滴加入25.9ml(416mmol)的甲基碘(1小时,温度<90℃)。然后,将该内部温度在80~90℃下保持另外的1.5小时。该冷却的批料倒入1000ml的冰水中,搅拌该混合物20分钟,抽滤出得到的固体,用水和甲醇洗涤,自甲苯重结晶六次,得到淡黄色固体,产率77%(21.4g),纯度>99.9%。
实施例2:合成其他单体
另外的如下所述单体M2~M5的合成描述于WO 03/020790和在其中所引用的文献中。
实施例3:合成聚合物
如WO 03/048225中所述,通过SUZUKI偶联合成根据本发明的聚合物和比较的聚合物。根据本发明合成的聚合物P1和P2的成分和比较的聚合物C1和C2的成分注明在表1中。比较的聚合物C1和C2具有与单体M1不同的单体,其得到聚合物中通式(1)的单元。
实施例4:PLEDs的制造
研究聚合物在PLEDs中的用途。在每一情况下该PLEDs是两层体系,即基材//ITO//PEDOT//聚合物//阴极。PEDOT是聚噻吩衍生物(从H.C.Starck,Goslar获得Baytron P)。所有情况中的阴极是Ba/Ag(Aldrich)。生产OLEDs的方法详细地描述在WO 04/037887和在其中引用的文献中。
实施例5~8:器件实施例
在PLEDs中使用根据本发明的聚合物P1和P2得到的结果同样显示于表1中。也显示出使用比较的聚合物C1和C2获得的电致发光结果。
如从结果中可见,根据本发明的聚合物的效率比比较的聚合物的效率更好。发光颜色是可比的,考虑该因素时寿命显著改进。这显示出根据本发明的聚合物比现有技术的聚合物更适用于显示器中。
表1:
实施例 | 聚合物 | 单体 | 最大效率/cd/A | U100cd/m2/V | CIE x/ya | 寿命b/小时 |
5 | P1 | 10%M150%M220%M310%M410%M5 | 7.7 | 2.8 | 0.16/0.24 | 400 |
6 | P2 | 2%M150%M246%M32%M5 | 6.02 | 3.3 | 0.15/0.19 | 1200 |
7 | C1 | 50%M230%M310%M410%M5 | 4.66 | 3.9 | 0.17/0.30 | 180 |
8 | C2 | 50%M246%M32%M42%M5 | 4.70 | 4.7 | 0.17/0.26 | 449 |
a CIE座标:The Commission Internationale de l’Eclairage(国际照明协会)1931的彩色坐标
b 寿命:直到亮度下降到初始亮度50%时的时间,初始亮度为400cd/m2
Claims (14)
1.一种聚合物,其包含通式(1)的单元,
其中
R每一次出现相同或不同,表示具有1~25个碳原子的直链烷基链、具有3~25个碳原子的支化烷基链或具有3~25个碳原子的环状烷基链,其中另外一个或多个非相邻的碳原子可以被=N-R1、-O-、-S-、-O-CO-O-、-CO-O-、-CH=CH-或-C≡C-取代,以及其中另外一个或多个H原子可以被F或CN替代,或者具有5~20个碳原子的芳香环系或具有2~20个碳原子的杂芳环系,它们可被一个或多个非芳基R1取代;此处两个基团R也可以彼此形成其他的单或多环的芳香或脂肪环系;
R1每一次出现相同或不同,表示H,具有1~22个碳原子的直链烷基链、具有3~22个碳原子的支化烷基链或具有3~22个碳原子的环状烷基链,其中另外一个或多个非相邻的碳原子可以被=N-R2、-O-、-S-、-O-CO-O-、-CO-O-、-CH=CH-或-C≡C-替代,以及其中另外一个或多个H原子可以被F或CN替代,或者具有5~40个碳原子的芳基、杂芳基、芳氧基或杂芳氧基基团,它们还可以被一个或多个非芳基R1取代;此处两个或多个基团R1彼此和/或与R也可以形成单或多环的脂肪或芳香环系;或者是F、Cl、Br、I、CN、N(R2)2、Si(R2)3或B(R2)2;
R2每一次出现相同或不同,是H或者具有1~20个碳原子的脂肪或者芳香烃基团;
X是C;
n每一次出现相同或不同,是0、1、2或3;
m每一次出现相同或不同,是0、1或2;以及
此处虚线键表示聚合物中的链接,
其中通式(1)单元的比例为至少5mol%,
其中除通式(1)的单元外,所述聚合物还包含其它结构要素,所述其它结构要素能提高空穴注入和/或传输特性和/或增加电子注入和/或传输特性,
2.根据权利要求1的聚合物,其特征在于至少一个或两个基团R不等于H。
3.根据权利要求1或2的聚合物,其特征在于它们是共轭或者部分共轭的聚合物。
4.根据权利要求1或2的聚合物,其特征在于除通式(1)的单元外,它们包含其它结构要素,该其它结构要素具有根据权利要求1的单个单元的组合。
5.根据权利要求1或2的聚合物,其特征在于除通式(1)的单元外,它们包含其它结构要素,该其它结构要素选自包括Ru、Os、Rh、Ir、Pd或Pt的结构单元并能改变发光特性到这样的程度,使得能够获得电致磷光而非电致发光。
6.根据权利要求1或2的聚合物,其特征在于除通式(1)的单元外,它们包含其它结构要素,该其它结构要素能改进从单重态到三重态的跃迁,并选自咔唑和桥联咔唑二聚单元、酮、氧化膦、亚砜和砜。
7.根据权利要求1或2的聚合物,其特征在于除通式(1)的单元外,它们包含其它结构要素,该其它结构要素能影响聚合物形态和/或发光颜色,并选自1,4-亚苯基、1,4-亚萘基、1,4-或9,10-亚蒽基、1,6-、2,7-或4,9-亚芘基、3,9-或3,10-亚二萘嵌苯、4,4′-亚联苯基、4,4″-亚三联苯基、4,4′-亚-1,1′-联萘基、4,4′-亚二苯乙炔基或4,4′-亚芪基。
8.根据权利要求1或2的聚合物,其特征在于通式(1)的单元经由3,9-链接结合在聚合物中。
9.一种根据权利要求1~8至少一项的一种或多种聚合物与其他聚合的和/或低分子量的物质的共混物。
10.一种根据权利要求1~8至少一项的一种或多种聚合物或者根据权利要求9的共混物在一种或多种溶剂中的溶液和制剂。
11.根据权利要求1~8至少一项的聚合物、根据权利要求9的共混物或根据权利要求10的溶液在发光二极管中的用途。
12.一种具有一个或多个活性层的有机电子组件,其特征在于这些活性层的至少一个包括根据权利要求1~8至少一项的一种或多种聚合物或者根据权利要求9的共混物。
13.根据权利要求12的有机电子组件,其特征在于它是聚合物发光二极管、有机集成电路、有机场效应晶体管、有机薄膜晶体管、有机太阳能电池或有机激光二极管。
14.根据权利要求13的有机电子组件,其特征在于它是聚合物发光二极管。
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DE102006031991A DE102006031991A1 (de) | 2006-07-11 | 2006-07-11 | Elektrolumineszierende Polymere und ihre Verwendung |
PCT/EP2007/005500 WO2008006454A1 (de) | 2006-07-11 | 2007-06-22 | Elektrolumineszierende polymere und ihre verwendung |
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JP5617150B2 (ja) * | 2005-11-11 | 2014-11-05 | 住友化学株式会社 | 共役高分子化合物およびそれを用いた高分子発光素子 |
US20120116050A1 (en) * | 2009-06-15 | 2012-05-10 | Technische Universitaet Graz | Pyrene-based polymers for organic light emitting diodes (oleds) |
KR20110104765A (ko) * | 2010-03-17 | 2011-09-23 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 |
RU2572414C2 (ru) * | 2013-08-29 | 2016-01-10 | Федеральное государственное бюджетное учреждение науки Институт проблем химической физики Российской академии наук (ИПХФ РАН) | Органическое люминесцентное вещество на основе производных пирена и электролюминесцентное устройство, содержащее это вещество |
KR101759238B1 (ko) | 2013-09-05 | 2017-07-18 | 제일모직 주식회사 | 유기 광전자 소자용 화합물, 이를 포함하는 유기 광전자 소자 및 상기 유기 광전자 소자를 포함하는 표시장치 |
KR102220425B1 (ko) | 2014-03-10 | 2021-02-26 | 삼성디스플레이 주식회사 | 화합물 및 이를 포함한 유기 발광 소자 |
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CN104017586B (zh) * | 2014-05-29 | 2015-07-15 | 京东方科技集团股份有限公司 | 液晶化合物、液晶组合物及其制备方法、液晶显示面板 |
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