TWI330645B - Polymeric charge transport compositions and electronic devices made with such compositions - Google Patents
Polymeric charge transport compositions and electronic devices made with such compositions Download PDFInfo
- Publication number
- TWI330645B TWI330645B TW092118922A TW92118922A TWI330645B TW I330645 B TWI330645 B TW I330645B TW 092118922 A TW092118922 A TW 092118922A TW 92118922 A TW92118922 A TW 92118922A TW I330645 B TWI330645 B TW I330645B
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- Prior art keywords
- group
- aryl
- heteroaryl
- integer
- alkyl
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- 239000000203 mixture Substances 0.000 title claims description 56
- 125000003118 aryl group Chemical group 0.000 claims description 105
- 125000001072 heteroaryl group Chemical group 0.000 claims description 84
- 229920000642 polymer Polymers 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 239000000178 monomer Substances 0.000 claims description 44
- 125000003342 alkenyl group Chemical group 0.000 claims description 40
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 33
- 125000000304 alkynyl group Chemical group 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 18
- -1 p-pyridyl group Chemical group 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000005024 alkenyl aryl group Chemical group 0.000 claims description 13
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000005025 alkynylaryl group Chemical group 0.000 claims description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 11
- 125000006612 decyloxy group Chemical group 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
- 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 9
- 125000006267 biphenyl group Chemical group 0.000 claims description 9
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 9
- 125000005217 alkenylheteroaryl group Chemical group 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 6
- 150000003573 thiols Chemical class 0.000 claims description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 229910052707 ruthenium Inorganic materials 0.000 claims description 5
- 229920001519 homopolymer Polymers 0.000 claims description 4
- 150000002923 oximes Chemical class 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 125000005129 aryl carbonyl 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 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 125000005015 aryl alkynyl group Chemical group 0.000 claims 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims 3
- 239000012964 benzotriazole Substances 0.000 claims 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- LXNHXLLTXMVWPM-UHFFFAOYSA-N Vitamin B6 Chemical class CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 230000000423 heterosexual effect Effects 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 1
- 239000011677 pyridoxine Chemical class 0.000 claims 1
- 235000008160 pyridoxine Nutrition 0.000 claims 1
- 125000002181 pyridoxine group Chemical class 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 239000000052 vinegar Substances 0.000 claims 1
- 235000021419 vinegar Nutrition 0.000 claims 1
- 229940011671 vitamin b6 Drugs 0.000 claims 1
- 239000010410 layer Substances 0.000 description 65
- 230000032258 transport Effects 0.000 description 27
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- 239000011148 porous material Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 238000010586 diagram Methods 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000003446 ligand Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 239000002800 charge carrier Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 210000003296 saliva Anatomy 0.000 description 3
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 238000007646 gravure printing Methods 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- UABNNDYJUIQZQZ-UHFFFAOYSA-N 1-(4-chlorobenzoyl)-2-(3,4-dimethoxyphenyl)-2,3a-dihydro-1h-pyrrolo[1,2-a]quinoline-3,3-dicarbonitrile Chemical class C1=C(OC)C(OC)=CC=C1C1C(C#N)(C#N)C(C=CC=2C3=CC=CC=2)N3C1C(=O)C1=CC=C(Cl)C=C1 UABNNDYJUIQZQZ-UHFFFAOYSA-N 0.000 description 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
- MNFZZNNFORDXSV-UHFFFAOYSA-N 4-(diethylamino)benzaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C=C1 MNFZZNNFORDXSV-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- OZOSHTUFPYREHG-UHFFFAOYSA-N 4-phosphanylbenzenethiol Chemical compound PC1=CC=C(S)C=C1 OZOSHTUFPYREHG-UHFFFAOYSA-N 0.000 description 1
- 241000208340 Araliaceae Species 0.000 description 1
- 101100323621 Drosophila melanogaster Drip gene Proteins 0.000 description 1
- 101100136092 Drosophila melanogaster peng gene Proteins 0.000 description 1
- QCWPXJXDPFRUGF-UHFFFAOYSA-N N1C=2C=C(N=3)C=CC=3C=C(N3)C=CC3=CC(=N3)C=CC3=CC1=CC=2C1=CC=CC=C1 Chemical compound N1C=2C=C(N=3)C=CC=3C=C(N3)C=CC3=CC(=N3)C=CC3=CC1=CC=2C1=CC=CC=C1 QCWPXJXDPFRUGF-UHFFFAOYSA-N 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- KWNKLEBXWBFYPB-UHFFFAOYSA-N [Ru].[Sn]=O.[In] Chemical compound [Ru].[Sn]=O.[In] KWNKLEBXWBFYPB-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 125000005418 aryl aryl group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- NKBNCXCSPQPNGS-UHFFFAOYSA-N benzene-1,2-dicarbonitrile;copper Chemical compound [Cu].N#CC1=CC=CC=C1C#N NKBNCXCSPQPNGS-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 150000004696 coordination complex Chemical class 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
- 125000004122 cyclic group Chemical group 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 239000011521 glass Substances 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
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- 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
- C07C211/44—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 only one six-membered aromatic ring
- C07C211/49—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 only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
-
- 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
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- Indole Compounds (AREA)
Description
玖、發明說明: 挺ji申請案之前彳 本案係自美國臨時申請案序號60/394767號,2002年7月 10曰申5月,及美國臨時申請案序號6〇/458277號,2〇〇3年3 月2 8曰申請提出優先權申請。 【發明所屬之技術領域】 本發明係關於一種聚合電荷傳送組合物。本發明進一步 係關於-種感光電子裳置中至少有―種包含該電荷傳 送組合物之声性層。 【先前技術】 在有機感光電子裝置如構成OLED顯示裝置之發光二極 體(OLED")中’有機活性層夾在〇LED顯示裝置内之二電接 觸層之間。在OLED中,在施加電壓越過電接觸層時,有機 感光層透過光傳輸電接觸層發光。 已知使用有機電發冷光化合物作為發光二極體之活性組 份。曾經使用簡單有機分子、共軛聚合物及有機金屬錯合 物。 使用感光物質之裝置時常包括一或多層電荷傳送層,其 定位於感光(例如,發光)層與接觸層之一之間。孔傳送声 可定位於感1光層與孔發射接觸層之間,亦稱為陽極。電:
傳送層可定位於感光層與電子發射接觸層之間,亦稱為阶 極。 K 對於電荷傳送物質有持續需要。 86574 1330645 【發明内容】 本發明係關於-種電荷傳送組合物,其為低聚合物或聚 合物。本文所用之術語"聚合物"之範圍意指包括具有—個 或多個不同類型單體單元之聚合物極低聚合物並意指具有 至少二個重複單體單元之化合物。術語"聚合性"意指具有 如聚合物之相同範圍。 在〃租例中,本發明係關於一種具有至少一個具有圖 1A之式1(a)之第一單體單元之聚合電荷傳送組合物,其中:
Ar在每^次出現可為相同或不同並選自芳基及雜芳基;
Ar2在每次出現可為相同或不同並選自伸芳基及雜伸芳 基; 雜烧基 、CnHaFb -員環; R在每次出現可為相同或不同並選自Η、烧基、 、芳基、雜芳基、芳基伸烷基、雜芳基伸烷基 、及C6HeFd ;或鄰接R1基可接合以形成5_或6 η為一弩數;及 a、b、c、及d為 〇或整數,使a+b = 2n+i,及c + d=5。 在一具體例中,本發明係關於一種具有至少一個具有式 1(b)之第一單體單元之聚合電荷傳送組合物其
Ar在每次出現可為相同或不同並選自芳基及雜芳美 86574 1330645
Ar2在每次出現可為相同或不同並選自伸芳基及雜伸芳 基; R3在每次出現可為相同或不同並選自Η、ρ、α、Br、經 基、羧基、羰基、甲矽烷基、矽氧基、烷基、雜烷基 、烯基、炔基'芳基、雜芳基、伸烷基芳基、烯基芳 基 '炔基芳基、伸烷基雜芳基、烯基雜芳基、炔基雜 芳基、CnHaFb、〇CnHaFb、C6HeFd及 〇C6HcFd,或 V二 者一起可構成伸芳基或雜伸芳基; a、b、2、:及 d為 〇 或整數,使 a+b = 2n+l,及 c + d=5 ; η為一整數(如上所述); y為0或1至3之整數;及 z為0或1至4之整數。 在一具體例中,本發明係關於一 1C之式1(c)之第一單體單元之聚合# 不I明係關於一種具有至少一個具有圖 單體單元之聚合電荷傳送組合物,其中:
Ar在母-欠出現可為相同或不同並選自
Ar2在每次出現可為相同或不同並選 基, ' 3芳基及雜芳基;--自伸芳基及雜伸芳 适自H、烷基、雜烷基 雜芳基伸烷基、CnHaFb R1在母次出現可為相同或不同並選自 、芳基、雜芳基、芳基伸烷基、雜 86574 W45 、及C^HeFd ;或鄰接R1基可接合以形成5_或6_員環; 汉在母次出現可為相同或不同並選自H、F、Cl、Br、經 基、羧基、羰基、甲矽烷基、矽氧基、烷基、雜烷基 、烯基、炔基、芳基、雜芳基、伸烷基芳基、烯基芳 基、炔基芳基、伸烷基雜芳基、烯基雜芳基、炔基雜 芳基、CnHaFb、〇CnHaFb、C6HcFd及 〇C6HcFd,或 R5二 者一起可構成伸芳基或雜伸芳基; a b、c、及d為 〇 或整數,使a + b = 2n+l,及c + d = 5 ; η為—整數(如上所述); y為0或i至3之整數;及 z為〇或1至4之整數。 在具體例中’本發明係關於一種具有至少一個具有圖 2A、2B及2C之式II(a)、11(13)及11((:)之第一單體單元之聚合 電何傳送組合物,其_ : R2及R3在每次出現可為相同或不同並選自H、F、a、Br 、烷基、雜烷基、烯基、炔基、芳基、雜芳基、CnHaFb 、〇CnHaFb、QHcFdoc^HcFd ; R4在每次出現可為相同或不同並選自伸烷基、雜伸烷基 、伸烯基、伸芳基、雜伸芳基、伸炔基、或伸芳基伸 炔基;· a b、c、及d為 0 或整數,使a+b = 2n+l,及 c + d = 5, η為一整數; Ρ為0或1 ; X為0、1或2;及 86574 哪45 y為〇或1至3之整數。 在一具體例中,本發明係關於一種具有至少一個具有圖 2Β及2C之式II(a)、11(13)及η⑷之第一單體單元之聚合 電荷傳送組合物,如上所述,且其中至少有一個取代 A p 义曰 t、CnHaFb、〇CnHaFb、之芳香族基上。 在一具體例中,本發明係關於一種具有至少—個具有附 圖所不之圖3A、3B、3C及4D之式III(a)、in(b)、Ιπ⑷及ΠΙ⑷ 之第單體單元之聚合電荷傳送組合物,其中: R在每二欠#現可為相同或不同並選自伸烷基、雜伸烷基 '伸烯基、伸芳基、雜伸芳基、或伸芳基伸炔基; R3在每次出現可為相同或不同並選自Η、f、cn' Br '經 基羧基、斂基、曱矽烧基、矽氧基、烧基、雜烧基 、烯基、炔基、芳基、雜芳基、伸烷基芳基、烯基芳 基、炔基芳基、伸烷基雜芳基、烯基雜芳基、炔基雜 芳基、CnHaFb、〇CnHaFb、C6HcFd& OC6HcFd,或 R5二 者一起可構成伸芳基或雜伸芳基; a ' b、c、及d為 〇 或整數,使 a + b = 2n+1,及 c + d = 5, η為一整數; X為0、1或2 ; y為0或1至3之整數;及 z為0或1至4之整數。 —· 在一具體例中,本發明係關於一種具有至少一個具有圖 ΙΑ、1B及1C之式i(a)、I(b)及I(c)之第一單體單元之聚合電 4傳达組合物及至少一個選自圖2八至2C之式11(3)至n(c)及 86574 10 1330645 上述圖3A至3D之式111(a)、111(b)、III(c)及111(d)之第二單體 單元之聚合電荷傳送組合物。 在一具體例中,本發明係關於一種電子裝置,具有至少 一活性層’其包含一個具有至少一個選自圖1A至1C、圖2A 至 2C及圖 3A至 3D之式 I(a)、1(b)、1(c)、11(a)、11(b)、11(c) 、111(a)、111(b)、ni(c)及111(d)之第一單體單元之聚合物, 其中Ar1、Ar2、R1至R3、a至d、η、ρ、及X至z定義如上。 在一具體例中,本發明係關於一種電子裝置,具有至少 一活性層J亭包含一個具有至少一個選自具有圖1Α至1C之 式1(a)、1(b)及1(c)之第一單體單元及至少一個選自圖2 a至 2C 之式 11(a)至 11(c)及上述圖 3A 至 3D 之式 III(a)、Hi(b)、ni(c) 及III(cl)之第二單體單元之聚合物。 本文所用之術語”電荷傳送組合物,,意指可接收來自電極 之電何亚可透過具有相當高效率及小電荷損失之物質厚度 促進移動之物質。孔傳送組合物可自陽極接收正電荷並傳 运之。電子傳送組合物可自陰極接收負電荷並傳送之。術 Γ抗猝減組合物"意指一種物質,其可防止阻滞或消除能 里轉移及電子轉移自感光層之激發狀態至鄰接層。術語 "感先性”意指任何顯示電發冷光性、光致發冷光性及/或光 敏性之物[術語”難〇|,意指化合物之最高佔據的分子軌 道美二Μ意指化合物之最低佔據的分子軌道。㈣ 二"思日化合物之—部分’如有機化合物内之取代基。 子首雜"意指一或多個碳原子 意指 … 反原千用不同原子更換。術語"烷基" 自具有-接附點之脂肪族煙衍生之基團,該基團可 86574 1330645 未經取代或經取代。術語,.雜 雜届工b曰‘ 自具有至少一個 雜原子及具有一接附點之脂肪 + ^ , L 團’該基團可 =代:經取代。術…基"意指—自脂肪族烴衍生 且二:或多個接附點之基團。術語"雜伸烧基"意指一自 ’、 ^個雜原子之脂肪族烴衍生並且;^ 4 & 點之基團。術語”烯基,,音指—自 有一或多個接附 埽丞心扣自具有一或多個碳-碳雙鍵之 亚具有—接附點之基團,該基團可未經取 代。術語,,块基"意指一自具有一或多個碳-碳三鍵之煙衍生 並具有^附點之基團’該基團可未經取代或經取代。術 浩伸烯基'’意指一自具有一.多 , ^ ^夕惘奴~石反雙鍵之烴衍生並 具有二或多個接附點之基團’該基團可未經取代或經取代 m申炔基”意指-自具有一或多個碳_碳三鍵之烴衍生 亚具有二或多個接附點之基團’該基團可未經取代或經取 代。術語”雜烯基"、"雜伸烯基"、"雜炔基"及"雜伸炔基" 意指具有Γ或多個雜原子之類似基團。術語"芳基"意指一 自具有-接附點之芳香族烴衍生之基團’該基團可未經取 代或經取代。術語”雜芳基"意指一自具有至少一個雜原子 並具有一接附點之芳香族基衍生之基團,該基團可未經取 代或經取代。術語"芳基伸録”意指—自具有芳基取代基 之烷基衍生L之基團,該基團可進一步未經取代或經取代。 術語’'雜彡基伸院基"意才旨—自具冑雜芳基取代基之烧基衍 生之基團,該基團可進—步未經取代或經取代。術語"伸芳 基"意指一自具有二接附點之芳香族烴衍生之基團,該基團 可未經取代或經取代。術語"雜伸芳基,,意指一自具有至少 86574 丄别645 原子並具有一接附點之芳香族基衍生之基團,該基團 可未經取代或經取代。術語"伸芳基伸烷基n意指一具有芳 土/、烷基且在芳基上具有一接附點而在烷基上具有一接附 點之^團。術語"雜伸芳基伸烷基,'意指一具有芳基與烷基 且在方基上具有一接附點而在烷基上具有一接附點之基團 丄且其中具有至少—個雜原子。除非另予指明,所有基團 白可未、丄取代或經取代。詞句"鄰接至",當用以指明為裝 置中之層蛉,亚非意指一層直接鄰接至另一層。另一方面 。司句接基”’意指在化學式中互相鄰接之r基(即,由 鍵連接之原子上之叫。術語”化合物,,意指未充電物質, 由進/由原子所組合之分子所構成,其中原子無法用物 理手&刀離。術語,,配位體,,意指接附至金屬離子之配位區 =分子、離子或原子。術語"錯合物",當用作名詞時, 具有至少一個金屬離子與至少一個配位體之化合物。 此外,完全使用IUPAC編號系統,其中自週期表之族自左 至右編號為!至18(化學與物理之CRc手冊第_,編 除非另予定義,本文所用之所有技術與科學術語具有如 熟習^發明所屬技術之-般者共同了解之相同意義。除非 :予疋義,圖式中所有字母符號代表原子及該原子縮 雖然類似0於本文所述之方法及物質可用 = 本發明,但適當方法及物f 飞。式驗 物、專利申請案、專利及=:下。本文所述之所有刊 及八他參考物皆以引例整個倂入。 在子論情況下,本說明書包括定義將受控制。此外 、方法及實例僅為例示性而非限制性。 物質 86574 -13- X下之、田節έ兒明及申請專利範圍當可明白本發明之其 他特性及優點。 【實施方式】 本發明之聚合組合物可用作電子傳送物質。其可單獨使 用或與其他物質一起使用。其可用作感光物質之宿主。 具有式1(a)至i(c)之三芳基曱烷_衍生物單體單元之聚合 物特別可用作孔傳送物質。 通常’ η為一整數。在一具體例中’ η為1至2〇之整數。在 具體例中η為1至1 2之整數。 在一具體例中,Λι·1選自苯基及聯苯基,其可具有一個或 夕個用雜原子替代之碳原子。所有此等基皆可進一步被取 代°取代基之例包括但不限於’烷基、雜烷基、芳基、雜 芳基 '芳基伸烷基、雜芳基伸烷基、CnHaFb、及C6HcFd, 其中a至d及η定義如上。 在一具體例中’ Ar2選自伸苯基及伸苯基伸烷基,其可進 一步被取代》 在一具體例中,N(R1 h為熔合雜芳香族環基。該基之例 包括但不限於’卡巴β坐、苯并二唾、及苯并三σ坐。 在—具體例中,R1選自具有1至12個碳原子之烷基、苯基 及苄基。二 具有式11(a)至11(c)之二氮雜菲-衍生物單體單元之聚合 物特別可用作電子傳送物質及抗猝減物質。 在一具體例中,R2選自苯基、聯苯基、吡啶基及二吡啶 基’其可進一步被取代。取代基之例包括但不限於,烷基 86574 -14- 1330645 、雜炫基 '芳基、雜芳基、芳基伸院基、雜芳基伸烧基、F 、(:nHaFb、〇CnHaFb、C6HcFd、及 0C6HcFd,其中 及 n定 義如上。 在一具體例中,至少一個R2選自苯基及聯苯基,且進一 步用選自 F、CnHaFb、〇CnHaFb、c6HcFd、及 〇C6HcFd之基團 取代其中a至d及η定義如上。 在一具體例中,R3選自具有1至1 2個碳原子之烧基。 在一具體例中,R4選自伸苯基、伸苯基伸烷基、伸烷基 及伸烯基。. 在一具體例中,至少有一個取代基在選自F、CnHaFb、 OCnHaFb、(:6HcFd、及OC6HcFd之芳香族環上,其中&至d及n 定義如上。 通常’ η為一整數。在一具體例中,^為1至2〇之整數。在 一具體例中,η為1至1 2之整數。 具有式Hl(a)、111(b)、111(c)、及111(d)之喹呤啉-衍生物單 體單元之聚合物且其中該等聚合物並非為均聚合物者,特 別可用作電子傳送物質及抗猝減物質。 通¥ ’η為一整數《在一具體例中,η為1至2〇之整數。在 一具體例中,η為1至1 2之整數。 在一具體i列中’ R4選自伸苯基、伸笨基伸烷基、伸烷基 及伸稀基。 在一具體例中,R5選自苯基烯基及笨基炔基,其可被進 一步取代。 在—具體例中,R5選自醋酸烷酯及芳基羰基,其可被進 86574 -15- 1330645 一步取代。 在一具體例中,R5選自具有1至12個碳原子之烷基。 在一具體例中,R5選自苯基、經取代苯基、吡啶基、及 經取代说咬基。取代基可選自F、C1、B r、經基、叛基、缓 基、甲矽烷基、矽氧基、烷基、雜烷基'烯基、炔基、芳 基、雜芳基、伸烷基芳基、烯基芳基、炔基芳基、伸烷基 雜芳基、烯基雜芳基、炔基雜芳基' CnHaFb' OCnHaFb、C6HeFd 及 OC6HcFd。 在一具體%中,二個鄰接R5 —起為雙伸芳基,其可進一 步被取代。在一具體例中’雙伸芳基係選自雙伸苯基及雙 伸吡啶基。取代基可選自F、C卜B r、羥基、缓基、幾基、 曱矽烷基、矽氧基、烷基、雜烷基、烯基、炔基、芳基、 雜芳基、伸烧基芳基 '烯基芳基 '块基芳基、伸院基雜芳 基、烯基雜芳基、炔基雜芳基、CnHaFb、、CeHUFd 及 OC6HeFd。 亦可在聚合結構中使用孔與電子傳送單體單元。在一冥 體例中,混合電荷傳送物f包含—種具有至少―個圖^至 1C之式I⑷至1(c)之第一 |體單元及至少—個選自圖2A至 2C之式Π⑷至π⑷及圖33D之式m⑷、m⑻、m⑷及 111(d)之第二^單體單元之聚合物。 取孔與電子傳送單體單元可與相同單體單元聚合以形成均 :::。纟亦可與一個或多個不同單體單元聚合以形成共 木&物。孔與電子傳送單體 — 早肢早70可互相或與其他單體單元 如一务基胺、芴、伸贫、从料,丄 勿伸本、伸笨伸乙烯、气二唾、。塞二唾、 86574 -16- 1330645 -唑、卡巴唑等共聚合。低聚合或聚合孔與電子傳 =例包括但不限於’圖从至4卜式IV⑷至IV(f)所示者,其 中· S與t可相同或不同且為以上之整數。 “ 應製備 進一步如實例所述 聚合物可使用已知合成技術如Suzuki或Yamamoto偶合反 1¾ , t隹—/-1 本發明之化合物可藉蒸發技術或傳統溶液加工法作為薄 膜應用。本文所用之術語,,溶液加r意指自液態介質形成 薄膜。液態介質可呈現溶液、分散液、乳液之形式或其他 形式。典2容液加工技術包括,例如,溶液鑄製、滴液缚 製、簾鎊製、方走塗、網目印刷、噴墨印刷、凹版印刷等。 電子裝詈 本發明亦關於一種電子裝置’包含至少一種定位於感光 層與一電極間之本發明之電荷傳送組合物。典型裝置結構 示於圖6 ^裝置1〇〇具有陽極層11〇及陰極層16〇。包含孔傳 送物質之層1 20鄰接陽極。包含電子傳送及/或抗猝減物質 之層140鄰接陰極。感光層13〇在孔傳送層與電子傳送/抗猝 減層之間。作為選擇,裝置時常使用鄰接陰極之另一電子 傳送層150。層120、130、140、及150個別及集合稱為活性 層。 端視裝置i 00之應用而定,感光層130可為發光層,其係 藉施加之電壓作動(如在發光二極體或發光電化學電池内) ’物質層,其回應輕射能量並使用或不使用施加之偏壓產 生信號(如在光檢測器内)。光檢測器之例包括光傳導電池 、光阻器、光控開關、光電晶體管 '光電管及光生伏打電 86574 17 1330645 池’該等術語敘述於 Markus, John,Electronics and
Nucleonics Dictionary, 470 and 476 (McGraw-Hill, Inc 1966)。 裝置之層可由任何已知用於該層之物質製得。陽極n 〇 為特別有效於注射正電荷載體之電極。其可由例如含有金 屬、混合金屬、合金、金屬氧化物或混合金屬氧化物之物 質製成’或其可為傳導聚合物及其混合物。適當金屬包括 族11金屬、族4 ’ 5及6金屬以及族8-10過渡金屬。若陽極將 光傳輸時」通常使用族12 ’ 13及14金屬之混合金屬氧化物 如銦-錫氧化物◊陽極丨丨〇亦可包含有機物質如聚苯胺,如 敘述於”由可溶性傳導聚合物製成之撓性發光二極體",
Nature ν〇1· 357’ PP 477-479 (1992年6月 11 日)。陽極與陰極 令至少一個應至少局部透明以容許看到一般光線。 本發明之三芳基甲烷衍生物聚合物,式I(a)至I(c),特別 可用作層1 20之孔傳送組合物。 可用於層120之其他孔傳送物質之例概述於,例如,
Kirk-Othmer Encyclopedia of Chemical Technology,第四版 ,Vol. 18, p. 837_86〇, 1996, γ Wang。可使用孔傳送分子 及聚合物。共用的孔傳送分子為:N,N,-二苯基-N,n,_雙(3_ 甲基苯基)-ΐ_1,Γ-二笨基]-4,4,-二胺(TPD)、1,1_雙[(二-4_甲 笨胺基)苯基環己烷(TAPC)、Ν,Ν,-雙(4-甲基笨基)_Ν,Ν,_雙 (4-乙基笨二曱基)二苯基]_44ι二胺(ETpD) 、肆-(3-甲基苯基)·Ν,Ν,ΝΙ,Νι_2,5_伸苯二胺(pc>A) ' a·苯基 -4-N,N-二苯基胺基笨乙烯(TPS)、對_(二乙基胺基)苄醛二 86574 •18· 1330645 苯基腙(DEH)、三苯胺(ΤΡΑ)、雙[4_(_n,n-二乙基胺基)_2_ 曱基笨基](4-甲基苯基)甲烷(MPMP)、;!-苯基_3_[對乙基 胺基)苯乙烯基]-5-[對-(二乙基胺基)苯基]吡唑啉(ppR = deasp)、1>2-反式-雙(9H_卡巴D坐冬基)環丁烧⑴czb)、 Ν,Ν,Ν',Ν·-肆(4-曱基苯基Η1,1·_二苯基)_4,4,_二胺(ΤΤΒ)、 及哺啉化合物如銅酞腈。共用的孔傳送聚合物為聚乙烯卡 巴唑、(苯基曱基)聚矽烷及聚笨胺及其混合物。亦可藉摻 雜上述孔傳送分子進入聚合物如聚苯乙烯及聚碳酸酯内而 得孔傳送聚合物。 感光層130之例包括所有已知電發冷光物質。以有機金屬 電發冷光化合物較佳。最佳化合物包括環狀金屬化銥及鉑 電發冷光化合物及其混合物。銥與苯基吡啶、苯基喳啉、 或苯基嘧啶配位體之錯合物作為電發冷光化合物揭示於 Petrov等人,公告PCT申請案w〇 〇2/〇2714號。其他有機金 屬錯合物敘述於,例如,公告申請案美國專利2〇〇1/〇〇19782 唬、歐洲專利1191612號、W0 02/15645號及歐洲專利 1191614號。具有摻雜有銥之金屬錯合物之聚乙烯卡巴唑 (PVK)之电發冷光裝置敘述於Burr〇ws and Thompson於公 告PCT申請案WO 00/70655號及WO 01/41 5 12號。包含電荷 負載宿主物j及發填光鉑錯合物之電發冷光發射層敘述於 ’ Thompson等人,美國專利6,3〇3,238號’ Bradley等人,於 Synth· Met. (2001) ’ 116 (1-3),379-383,及 Campbell 等人 ’於Phys. Rev. B,Vol. 65 08 52 10。一些適當銥錯合物之例 提供於圖6 ’如式V(a)至V(f)。亦可使用類似配位基鉑錯合 86574 -19- 1330645 物。此等電發冷光錯合物可單獨使用, 荷負載宿主内。本發明之聚合電从 Υ κ ,雜入電 a之+ σ電何傳送物質可 屬及其他發射物之宿主。 马有機金 本發明之二氮雜菲衍生物及心号啦衍生物聚合物 至11(C)、式III⑷至ΙΠ⑷,特別可用作層14〇内之電子^ ^ 抗猝減組合物,或用作層15。内之電子傳送組合物。本發: 之二氮雜菲衍生物及喹》号啉衍生物聚合物最好用作發‘二 極體内之電子傳送/抗猝減層。 可用於,150内之附加電子傳送物質之例包括金屬螯人· c—d化合物’如參(8_經基ρ奎諾基)铭(Ay;及唾化合: 如2_(4_二苯块基)-5-(4-第三了基苯基)-1,3,4-。号二。坐(PBD) 及3_(4_二苯炔基苯基-5-(4-第三丁基苯基)],2,4-三唑 (TAZ),及其混合物。 陰極1 60為種對注射電子或負電荷載體特別有效之電 極陰極_可為任何具有較陽極更低功函數之金屬戍非金屬 。陰極用之物質可選自族匕驗金屬(如Li,Cs)、族2(=) 金屬、族12金屬,包括稀土元素及鑭系元素及釣系元素。鲁 可使用物質如紹、钢、舞、鋇、彭及錯及其組合。含^有 機金屬化δ物,LiF及Li 2〇亦可沉積在有機層與陰極層之間 以降低操作壓。 已知在有機電子裝置内具有其他層。例如,在陽極110 與孔傳迗層120之間可具有一層(圊未示)以利正電荷傳送 及/或層之帶隙匹配或作為保護層功能。可使用此技藝已知 之層。此外,任何上述層可由二或多層製成。或者,某些 86574 -20· 1330645 二所有陽極層110、孔傳送層12〇、電子傳送 陰極層⑽可被表面處理以增加電荷載體傳送效^對各成 伤層物$之最好由平衡提供裝置具有 標決定。 且双手之曰 須知各官能層可由超過一層所構成。 裝置可藉各種技術,包括接库苄* 序?”、八,儿積個別層在適當基 衣備。可使用基材如玻璃及聚合膜。可使用傳統汽相 沉積技術如熱蒸發、化學汽相沉積等。或I,.有機層可使 用任何傳,塗佈或印刷技術,包括但不限於旋塗、浸塗、 輥-輥技術、喷墨印刷、凹版印刷、及網目印刷自溶=或分 散,於適當溶劑内塗佈。通常,$同層具有下面厚度範圍 •陽極110 ’ 500-5000埃’較佳為1〇〇〇2〇〇〇埃;孔傳送層 120’ 50-2000埃’較佳為2隊屬埃;感光層13〇,心2_ 埃,較佳為1〇〇-1〇〇〇埃;電子傳送層140及15〇,50_2〇〇〇埃 ’較佳為1G(M_埃;陰極⑽,2()(M⑽⑽埃,較佳為 3 00-5000&。電子·孔再組合區域於裝置内之位f 置之發射光譜可被各層之相對厚度影響。因此,應選擇電 子-傳送層之厚度,使得電子·孔再組合區域在發光層内。 層厚度之所欲比率端視所用物質之實際性質而定。 本發明之—三芳基曱烧、二氣雜菲衍生物及口奎十林衍生物 聚合物可用於OLEDs以外之應用。例如,&等組合物可用 於太陽能轉化之光生伏打裝置。其亦可用於場效電晶體供 精靈卡及薄膜電晶體(TFT)顯示驅動器應用。 、 86574 -2]- 1330645 實例 下列實例例示本發明之某種特性及優點。預定其為本發 明之例系性而非限制性。除非另予指明,所有百分比皆依 重量計。 實例1 此實例例示圖4所示之聚合物IV(c)之製備。
在氮氣下DMF (100毫升)加入la (3.96克,9毫莫耳)、 lb (3.63 克’ 9¾ 莫耳)、辞(4.0 克 ’ 61.2 宅旲耳)、NiCl2(0.23,4 克,1.80毫莫耳)、PPh3 (1.87克,7·2毫莫耳)及二吡啶(〇 29 克’ 1 · 8愛莫耳)之混合物内。所得混合物加熱至9 〇 歷4 8 小時。然後’將其冷卻至室溫並用稀釋。在過渡後 ’固體用CHKh洗滌,組合的有機層用in HC1及鹽水洗蘇 86574 -22- 1330645 。將溶液濃縮並自MeOH沉澱以得聚合物IV(c)。 實例2 此實例例示圖4A所示之聚合物IV(a)之製備。 以類似於對聚合物IV(c)所述之聚合程序製造聚合物IV(a)。
丨 V(a) 實例3 此實例例示圖4D所示之聚合物IV(d)之製備。 以類似於對聚合物IV(c)所述之聚合程序製造聚合物IV(d)。 86574 -23 - 1330645
IV(d) 貫例4 此實例例示圖4F所示之聚合物IV(f)之製備。
放在氮氣·下並設置狄恩-史塔克(Dean-Stark)截流器之圓 底燒瓶裝入4a (5毫莫耳,其係根據J. P. Chen等人’ Synthetic Metals 2003, 132, 1 73所述之程序合成)、苄醛4b (5毫莫耳) 、對甲苯磺酸(9.5毫莫耳)及氣苯(20毫升)。使所得混合物 回流3日,然後,聚合物自MeOH藉沉澱單離。 86574 -24- 1330645 實例5_ 此實例例示圖4E所示之聚合物IV(e)之製備。
在惰性氮氣環境下’圓底燒瓶裝入5a (0.5莫耳)、5b (0.5 莫耳)、Pd(OAC)2 (0.05 莫耳)、Ρ(〇τ〇ι)3 (〇 15 莫耳)、以川及 DMF。將所-得混合物回流3日,產物係藉CH2C12稀釋並自 MeOH沉澱單離。 【圖式簡單說明】 單元之式1(a)、1(b)及1(c) » 體單元之式11(a)、11(b)及 圖ΙΑ、1B及1C顯不電荷傳送單體 圖2A、2B及2C顯示電荷傳送單 11(c)。 86574 -25 - 1330645 圖3A、3B、3C及3D顯示電荷傳送單體單元之式111(a)、 111(b) 、 III(c)、及 111(d)。 圖4A、4B、4C、4D、4E及4F顯示本發明之聚合電荷傳 送組合物之式IV(a)至IV(f)。 圖5A及5B顯示電荷傳送單體單元之式5A及5B。 圖6為發光二極體(LED)之概略圖表。 圖7A、7B、7C、7D及7E顯示電發冷光銥錯合物之式V(a) 至 V(e)。 86574 26-
Claims (1)
- 拾、申請專利範圍: 一種組合物,其包含具有至少一個具有式1(a)之第 體單元之聚合物 —Α「2 — I Arl Ar1 1 (。) NR12 NR12 其中: Ar在每次出現可為相同或不同並選自芳基及雜芳基; Ar2在每次出現可為相同或不同並選自伸芳基及雜伸 芳基; R在每次出現可為相同或不同並選自Η、烷基、雜烷 基 '芳基、雜芳基、芳基伸烷基、雜芳基伸烷基 、CnHaFb、及c6HcFd ;或鄰接R1基可接合以形成5-或6-員環; η為整數;及 a、b、c、及d為 〇 或整數,使 a+b = 2n+l,及c + d = 5。 2,如申請專利範圍第1項之組合物,其中Ar1係選自苯基、 經取代苯基、聯笨基、經取代聯苯基、吡啶基、經取代 p比啶基^二吡啶基、及經取代二吡啶基。 - 3,如申請專利範圍第1項之組合物,其中^^尺^選自卡巴 唑、苯并二唑、及苯并三唑。 4.如申請專利範圍第1項之組合物,其中R1選自具有1至12 個碳原子之烷基、苯基及芊基。 86574 1330645 單 5. —種組合物,其包含具有至少一個具有式II(a)之第 體單元之聚合物 一 r4 — •(R?N^「(R3)x I I (α N 其中: R2及R3在每次出現可為相同或不同並選自H、F、 > Hr、烷基、雜烷基、烯基、炔基、芳基、雜芳 基、CnHaFb、〇CnHaFb、C6HcFd及 〇C6HcFd ; R4在每次出現可為相同或不同並選自伸烧基、雜伸烧 基、伸烯基、伸芳基、或雜伸芳基; a、b、c、及d為 0 或整數’使 a+b = 2n+l,及 c + d = 5, n為整數; ❻0或丨至3之整數; 、二其限制條件為至少有-個取代基在選自F、CnHaFt 6. 〜種、C及0C6HcFd之芳香族基上。 卜⑯’其包含具有至少—個具有式Η⑻之第一單 元之聚合物 8657411(b) 在每次出現可為相同或不同並選自H、F、 Br、院基、雜烧基、稀基、炔基、芳基、雜芳 4 基、CnHaFb、OCnHaFb、c6HcFd及 〇C6HcFd ; 在每次出現可為相同或不同並選自伸烷基、雜伸烷 基、伸烯基、伸芳基、或雜伸芳基; b、c、及d為0或整數,使a + b = 2n+1,及c Ώ為整數; Χ為0、- 1或2 ;及 -¾ 一 乂為0或1至3之整數; 但其限制條件為至少有一個取代基在選自F、 ' 〇C u t: n a b —nHaFb ' C6HcFdA 0C6HcFd2 芳香族基上。 一 j組合物,其包含具有至少一個具有式11(〇之第一單 體單元之聚合物其中: 及芒在母次出現可為相同或不同並選自Η' ρ、cl 、Br、烷基、雜烷基、烯基、炔基、芳基、雜芳 基、CnHaFb、〇CnHaFb、C6HcFd及 〇c6HcFd ; R在每次出現可為相同或不同並選自伸烷基、雜伸烷 基、伸稀基、伸芳基、或雜伸芳基; b、C、及d為 0 或整數,使 a + b = 2n+1,及 c + d = 5, n為整數; p為〇或1 ;及 y為〇或1至3之整數; L其限制條件為至少有一個取代基在選自F、CnHaFb 〇CnHaFb、C6HcFd及 OC6HcFd之芳香族基上。 申叫專利範圍第5,6或7項任—項之組合物,其中r2 係選自苯基、經取代苯基、聯苯基、經取代聯苯基、吡 疋土:,取代比咬基、二p比咬基、及經取代二峨咬基。 9.如申叫專利範圍第5,6或7項之組合物,其中r4選自伸 苯基、伸苯基伸烷基、伸烷基及伸烯基。 ίο. —種組合物,其包含具有至少一個具有之第一 單體單元之聚合物其中: 111(0) R4在每次出現可為相同或不同並選自伸烷基、雜伸烷 基、伸烯基、伸芳基、雜伸芳基、或伸芳基伸炔 基,; R5在每次出現可為相同或不同並選自Η、ρ、C1、Β·Γ 、羥基、羧基、羰基、甲矽烷基、矽氧基、烷基 、雜烷基、烯基、炔基、芳基、雜芳基、伸烷基 芳基、烯基芳基、炔基芳基、伸烷基雜芳基、稀 86574 1330645 基雜芳基、炔基雜芳基、CnHaFb、〇CnHaFb、C6HcFd 及〇C6HeFd,或R5二者一起可構成伸芳基或雜伸芳 基; a 卜及d為0或整數,使a+b = 2n+i,及c + d = 5, η為整數;及 ζ為0或1至4之整數,且其中該聚合物並非為均聚合物。 11· 一種組合物,其包含具有至少一個具有式^(勾之第一 單體單元之聚合物其中: R4在每次出現可為相同或不同並選自伸烷基、雜伸烷 基、伸烯基、伸芳基、雜伸芳基、或伸芳基伸炔 基; R在母··人出現可為相同或不同並選自Η、F、Cl、Br 、羥基、羧基、羰基、曱矽烷基、矽氧基、烷基 、雜烷基、烯基、炔基、芳基、雜芳基、伸烷基 芳基、烯基芳基、炔基芳基、伸烧基雜芳基 '烯 基@芳基、炔基雜芳基、CnHaFb、◦CnHaFb、 及OC6HeFd,或R5二者一起可構成伸芳基或雜伸芳 基; a、b、c、及d為 0 或整數,使a + b=2n+1,及c + d=5, η為整數;及 86574 1330645 x為0、1或2。 12.如申請專利範圍第10或11項之組合物,其中R4選自伸苯 基、伸苯基伸烷基、伸烷基及伸烯基。 1 3 ·如申請專利範圍第1 0或11項之組合物,其中R5係選自苯 基烯基、苯基炔基、醋酸烷酯基、芳基羰基、具有1至 1 2個碳原子之烷基、苯基、經取代苯基、吡啶基及經取 代峨σ定基。 1 4.如申請專利範圍第1 0或11項之組合物,其中二個鄰接R5 一起為一伸芳基。 •— 一 15_ —種物質,其包含具有至少一個具有式1(a)至1(c)之第 一單體單元之聚合物 —— I/c\ , Ar1 Ar1 NR12 NR1286574 -6 - 13306451(c) 及至少一個選自式11(a)至11(c)之第二單體單元 86574 — ra —I I (0)(R11(b) II (Ο |y III(α)1330645III (b)(R5)x III (〇) III (d) 其中: 在式 中: Ar在母_人出現可為相同或不同並選自芳基及雜芳義. 在母-人出現可為相同或不同並選自伸芳基及雜伸 芳基; R在母-人出現可為相同或不同並選自Η、烧基、雜烧 基二芳基、雜芳基、芳基伸烷基、雜芳基伸烷基 、CnHaFb、及C6HeFd ;或鄰接R1基可接合以形成5-或6-員環; n為整數;及 a、b、c、及d為 0 或整數,使 a+b = 2n+l,及 c + d = 5 ; 86574 1330645 在至 life)中: R2及R3在每次出現可為相同或不同並選自H、F、Cl 、Br、烷基、雜烷基、烯基 '炔基、芳基、雜芳 基 ' CnHaFb、OCnHaFb、C6HcFd及 〇C6HcFd ; R4在每次出現可為相同或不同並選自伸烷基、雜伸烷 基' 伸烯基、伸芳基、或雜伸芳基; a b、c、及d為 0 或整數’使a + b = 2n+l ’ 及c + d = 5, n為整數; Ρ為0或1 ; • - X為0、1或2 ;及 y為〇或1至3之整數; 八限制條件為至少有一個取代基在選自F、CnHaFb 〇CnHaFb ' c6hcF(^ 〇C6HcFd之芳香族基上; 在至 mm 中: R在每次出現可為相同或不同並選自伸烷基、雜伸烷 伸稀基、伸芳基、雜伸芳基、或伸芳基伸快 基; R在每次出現可為相同或不同並選自H、F、CM、Br 、經基基、甲錢基、錢基、烧基 二,燒基、稀基、炔基、芳基、雜芳基、伸烧基 方基、烯基芳基、炔基芳基、伸烷基雜芳基、^ 基雜芳基、快基雜芳基、CnHaFb、0CnHaFb、 :〇C6HcFd’或r5二者一起可構成伸芳基或雜伸芳 86574 1330645 a、b、c、及d為 0 或整數,使 a + b = 2n+l,及 c + d = 5, η為整數; χ為0、1或2 ; y為0、1或3 ;及 z為0或1至4之整數。 16. —種組合物,其包含具有至少一個選自式IV(a)至IV(e) 之第一單體單元之聚合物IV( α) IV(b-) 86574 • 10- 1330645IV( c)IV(d ) IV(e). 86574 -11 - 1330645 17. —種組合物,其包含具有至少一個具有式IV(f)之第一 單體單元之聚合物IV(f ). 18. —種電子裝置,其包含具有至少一個具有式1(a) ' 1(b) 或I(c:L之-·第一單體單元之聚合物之組合物86574 -12- 其中: 在每次出現可為相同或不同並選自芳基及雜芳基; Ar2在每次出現可為相同或不同並選自伸芳基及雜伸 芳基; Rl在每次出現可為相同或不同並選自Η、烷基、雜烧 基、芳基、雜芳基、芳基伸烷基、雜芳基伸烷基 、CnHaFb、及C6HcFd ;或鄰接R1基可接合以形成5_ 或6-員環; n為整歎; • ^ 一 y為 0、1、2或 3 ; 2為〇、1、2、3或4 ;及 a、b、c、及d為 0 或整數,使 a+b = 2n+l,及 c + d = 5。 19·如申請專利範圍第18項之裝置,其中Ari係選自笨基、 經取代笨基、聯苯基、經取代聯苯基、吡啶基、經取代 p比。定基、二吡啶基、及經取代二吡啶基。 2〇·如申請專利範圍第18項之裝置,其中n(ri)2選自卡巴唑 、笨并二唑、及苯并三唑。 21·如申請專利範圍第18項之裝置,其中Ri選自具有1至12 個碳原子之烷基、苯基及芊基。 22 ·—種電f裝置,其包含具有至少一個具有式II(a)之第〆 單體單元之聚合物之組合物 86574 丄:UIK)4!)R及R在每次出現可為相同或不同並選自H、f、c 、Br、烷基、雜烷基、烯基、炔基、芳基、雜芳 * 土 CnHaFb、〇cnHaFb、c6HcFd及 〇C6HcFd ; R在母次出現可為相同或不同並選自伸烷基、雜伸烷 基、伸缔基、伸芳基、或雜伸芳基; ^卜及d為〇或整數,使a + b = 2n+1,及c + d = 5, n為整數; X為0、1或2 ;及 0或1至3之整數; 、二其限制條件為至少有一個取代基在選自f 23. -種:叫之芳香族基上。& b 單體;H其包含具有至少—個具有式n(b)之第〜 疋之水合物之組合物 •RX 1(b) 其中: 86574 及R在每次出現可為相同或不同並選自H' p、d Br、烷基、雜烷基、烯基、炔基、芳基、雜芳 基、CnHaFb、〇CnHaFb、C6HcFd及 〇c6HcFd ; 在每次出現可為相同或不同並選自伸烷基、雜伸烷 基、伸稀基、伸芳基、或雜伸芳基; _ b c、及d為〇或整數,使a+b = 2n+l ,及c + d=s n為整數; X為0、1或2 ;及 1至3之整數; 〜其限制條件為至少有一個取代基在選自F、c η P 〇C U V n a b 24. nWaFb、C6HcFd及OC6HcFd之芳香族基上。 種電子裝置’其包含具有至少一個具有式II(C)之第一 單元之聚合物之組合物11(c)其中: R2及R3在每次出現可為相同或不同並選自H、F、C1 、三r、烷基、雜烷基、烯基、炔基、芳基、雜芳 基、CnHaFb、OCnHaFb、C^HcFc^OC^HcFd ; R4在每次出現可為相同或不同並選自伸烷基、雜伸烷 基、伸烯基、伸芳基、或雜伸芳基; a、b、c、及d 為 〇 或整數’使 a+b = 2n+l ’ 及 c + d=5, 86574 -15- η為―整數; Μ 0或1 ;及 % 0或1至3之整數; L其限制條件為至少有一個取代基在選自F、CnHaFb nHaFb、c6HeFd及 〇C6HcFd之芳香族基上。 •如申請專利範圍第22,23或24項中任一項之裝置,其中 仏選自笨基、經取代苯基、聯笨基、經取代聯苯基、 吡啶基、經取代吡啶基、二吡啶基、及經取代二吡啶 基。 6.如申請專利範圍第22,23或24項之裝置,其中R4選自伸 苯基、伸笨基伸烷基、伸烷基及伸烯基。 2 7. —種電子裝置,其包含具有至少—個具有式111(幻之第 一單體單元之聚合物之組合物111(a) 其中: R在每次出現可為相同或不同並選自伸烷基、雜伸烷 基 '伸烯基、伸芳基、雜伸芳基、或伸芳基伸炔 基,; R3在每次出現可為相同或不同並選自Η、F、ci、 、經基、缓基、羰基、曱矽烷基、矽氧基、烷基 、雜烷基、烯基、炔基、芳基、雜芳基、伸烷基 芳基、烯基芳基、炔基芳基、伸烷基雜芳基、烯 86574 -16· 1330645 基雜芳基、块基雜芳基、 及 OC6HcFd,或 R5 二者一 基; CnHaFb、〇CnHaFb、C6HcFd 起可構成伸芳基或雜伸芳 、' c '及ύ為〇或整數,使a+b=2n+1,及c+d=5, η為整數;及 ζ為0或1至4之整數。 28·種包子裝置,其包含具有至少-個具有式111(b)至 111(d)之第_ f體單元之聚合物之組合物 二4^X^~(r5)x ιπ (b) (R5)xHI (C)(r5)xIII (d)其中 R在每次出現可為相同或不同並選自伸烷基、雜伸烷 基、伸烯基、伸芳基、雜伸芳基、或伸芳基伸炔 基; R在每次出現可為相同戒不同並選自H、F、Cl、Br 86574 •17- 1330645 、羥基、羧基、羰基、甲矽烷基、矽氧基、烷基 、雜烷基、烯基、炔基、芳基、雜芳基、伸烷基 芳基、烯基芳基、炔基芳基、伸烷基雜芳基、烯 基雜芳基、炔基雜芳基、(:nHaFb、OUPb、e6HePd 及OC6HeFd,或R 一者一起可構成伸芳基或雜伸芳 基; a、b、c、及d為 0 或整數’使 a + b = 2n+l,及 c + d = 5, η為整數; X 為 0、_ 1 或 2 ; y為〇、1、2或3 ;及 z為 0、1、2、3 或 4。 29.如申請專利範圍第27或28項之裝置,其中R4選自伸苯基 、伸苯基伸烷基、伸烷基及伸烯基。 3 0.如申請專利範圍第27或28項之裝置,其中R5係選自苯基 烯基、苯基炔基、醋酸烧醋基、芳基幾基、具有1至12 個碳原子之烷基、苯基、經取代苯基、吡啶基及經取代 吡啶基。 3 1 ·如申請專利範圍第27或28項之裝置,其中二個鄰接R5 起為二伸芳基。 種電f裝置,其包含具有至少一個具有式1(a)至1(c) •^第一單體單元之聚合物之物質 86574 1330645 Ar2Α广2 I (c 及至少一個選自式11(a)至11(c)之第二單體單元 R4·II (α 86574 19 1330645II(b 11(c)及式 IIIU)至 111(d)III(a) III(b)/ III (OIII (d)86574 20· 1330645 其中: 在式1(a)至ΙΟΛ中·_ Αγ1在每次出現可為相同或不同並選自芳基及雜芳基; Ar2在每次出現可為相同或不同並選自伸芳基及雜伸 芳基; R1在每次出現可為相同或不同並選自Η、烷基、雜烷 基、芳基、雜芳基、芳基伸烷基 '雜芳基伸烷基 、CnHaFb、及C6HeFd ;或鄰接R1基可接合以形成5_ 或6.-員環; η為整數; y為0、1、2或3; z為〇、1、2、3或 4;及 a、b、c、及d為 0 或整數,使 a+b = 2n+1,及 c + d = 5 ; 曼 IKc、中: R及R3在每次出現可為相同或不同並選自H、f、d Br、院基、雜烧基、稀基、炔基、芳基、雜芳 基、CnHaFb、OCnHaFb、C6HeFd及 OC6HcFd ; R4在每次出現可為相同或不同並選自伸烷基、雜伸燒 基、伸烯基、伸芳基、或雜伸芳基; a' b^c、及d為 〇 或整數,使a + b = 2n+l,及 c + d = 5 , n為整數; P為0或1 ; x為0、1或2 ;及 y為0或1至3之整數; 86574 但其限制條件為至少有一個取代基在選自F、CnHaFb 、〇CnHaFb、C6HcFd及 0C6HcFd之芳香族基上; 支又 111(a)至_ TTTM、中—_ R在每次出現可為相同或不同並選自伸烷基、雜伸烷 基、伸烯基、伸芳基、雜伸芳基、或伸芳基伸炔 基; 在每次出現可為相同或不同並選自H、F、C卜Br 、羥基、羧基'羰基、曱矽烷基、矽氧基、烷基 二,烷基、烯基、炔基、芳基、雜芳基、伸烷基 芳基、烯基芳基、炔基芳基、伸烷基雜芳基、烯 基雜芳基、炔基雜芳基、CnHaFb、OHFb、GHJd 及〇C6HcFd,或R3二者一起可構成伸芳基或雜伸芳 基; a b、c、及 d為 0 或整數,使 a + b = 2n+1,及 c + d=5, n為整數; χ為0、1或2 ; y為〇、1、2或3 ;及 z為〇或1至4之整數。 33. 一種電子裝置,其包含具有至少一個選自式1¥(3)至IV(e) 之第一号體單元之聚合物之組合物 86574 -22- 1330645IV(b-)86574 -23- 1330645IV(e). 34. —種電子裝置,其包含具有至少一個具有式IV(f)之第 一單體單元之聚合物之組合物IV(干). 3 5. —種組合物,其包含具有至少一個具有式1(b)或1(c)之 第一單體單元之聚合物 86574 •24 -1330645 n,r12 Αγ1其中: Αι^在每_人出現可為相同或不同並選自芳基及雜芳基; “在每次出現可為相同或不同並選自伸芳基及 芳基; R在每次出現可為相同或不同並選自h、f、c卜以 羥基、羧基、羰基、甲矽烷基、矽氧基、烷基 、雜烷基、烯基、炔基、芳基、雜芳基、伸烷= 方基、稀基芳基、块基芳基、伸燒基雜芳基、缔 基雜芳基、块基雜芳基、(:nHaFb、〇CnHaFb、c啦 :0C6HeFd ’或r5二者一起可構成伸芳基或雜伸芳d a、b、C' 及d為 〇或整數,使a + b = 2n+i,及c + , n為整數(如上所述); -25- 36. y為〇或1至3之整數; Ζ為0或1至4之整數;及 其中該聚合物並非主 卫非為岣聚合物。 種、'且。4勿,其包含具有至少-個具有式111(C)或111(d) 之第一單體單元之聚合物I I I (d ) 其中: R在每次出現可為相同或不同並選自伸烷基、雜伸烷_ 基、伸稀基、伸芳基、雜伸芳基、或伸芳基伸炔 基; R5在,次出現可為相同或不同並選自H、F、CM、Br 、羥基、羧基、羰基、曱矽烷基、矽氧基、烷^ 、雜烷基、烯基、炔基、芳基、雜芳基、伸烷基 芳基、烯基芳基、炔基芳基、伸烷基雜芳基、稀 基雜芳基、炔基雜芳基、CnHaFb、0CnHaFb、c6HcFd 86574 •26- 及0C6HeFd,或R5二者,起可構成伸芳基或雜伸芳 基; D、c、及d 為 0 或整數,使a+b = 2n+l,及 c + d = 5, n為整數; X為0、1或2 ; 37. 或1至3之整數;及 其中該聚合物並非為均聚合物。 種組合物,其包含具有玄少一個具有式III(b)之第— 單體單元之聚合物 • ^ -111(b). 其中: R4在每次出現可為相同或不同並選自伸烷基、雜伸燒 基、伸烯基、伸芳基、雜伸芳基、或伸芳基伸炔 基; ' R3在每次出現可為相同或不同並選自h、f、cn、Bf 、羥基、羧基、羰基、曱矽烷基'矽氧基、院基 、墼烷基、烯基、炔基、芳基、雜芳基、伸烷基 芳基、烯基芳基、炔基芳基、伸烷基雜芳基、士 基雜芳基、炔基雜芳基、CnHafb、〇CnHaFb、 及OC6HeFd,或R3二者一起可構成伸芳基或雜伸 基; 86574 -27· 1330645 a ' b ' c ' 及 d 為 0 或整數,使 a + b = 2n+l,及 c + d = 5, n為整數; X為0、1或2 ;及 其中該聚合物並非為均聚合物。 3 8. —種包含物質層之裝置,該物質層包含如申請專利範圍 第35、36或37項聚合物。 3 9.如申請專利範圍第18或38項之裝置,其中該裝置為發光 二極體、發光電化學電池或光檢測器。 86574 -28 -
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