TW200403229A - Charge transport compositions and electronic devices made with such compositions - Google Patents
Charge transport compositions and electronic devices made with such compositions Download PDFInfo
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- TW200403229A TW200403229A TW092118886A TW92118886A TW200403229A TW 200403229 A TW200403229 A TW 200403229A TW 092118886 A TW092118886 A TW 092118886A TW 92118886 A TW92118886 A TW 92118886A TW 200403229 A TW200403229 A TW 200403229A
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- Prior art keywords
- group
- heteroaryl
- item
- aryl
- composition
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 99
- 150000001875 compounds Chemical class 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- -1 bulk Chemical group 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 22
- 125000000732 arylene group Chemical group 0.000 claims description 18
- 125000005549 heteroarylene group Chemical group 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000005024 alkenyl aryl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000005025 alkynylaryl group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
- 125000005217 alkenylheteroaryl group Chemical group 0.000 claims description 8
- 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims description 8
- 150000003248 quinolines Chemical class 0.000 claims description 8
- 150000002430 hydrocarbons Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 125000005275 alkylenearyl group Chemical group 0.000 claims description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 150000003252 quinoxalines Chemical class 0.000 claims description 3
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 claims 7
- 125000004474 heteroalkylene group Chemical group 0.000 claims 7
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims 5
- 150000004756 silanes Chemical class 0.000 claims 2
- WKAXDAMWMOBXMP-UHFFFAOYSA-N 2,3-diphenylpyridine Chemical class C1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=C1 WKAXDAMWMOBXMP-UHFFFAOYSA-N 0.000 claims 1
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims 1
- 125000006416 CBr Chemical group BrC* 0.000 claims 1
- 102000017795 Perilipin-1 Human genes 0.000 claims 1
- 108010067162 Perilipin-1 Proteins 0.000 claims 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- 125000003435 aroyl group Chemical group 0.000 claims 1
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 150000007857 hydrazones Chemical class 0.000 claims 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- 229940074404 sodium succinate Drugs 0.000 claims 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical group [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 claims 1
- 239000004575 stone Substances 0.000 claims 1
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 83
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 238000002360 preparation method Methods 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 239000000126 substance Substances 0.000 description 24
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- 229940125904 compound 1 Drugs 0.000 description 17
- 239000000463 material Substances 0.000 description 17
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 12
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000005842 heteroatom Chemical group 0.000 description 10
- 230000005855 radiation Effects 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 238000004293 19F NMR spectroscopy Methods 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000005401 electroluminescence Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 238000012546 transfer Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 125000005647 linker group Chemical group 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229910052741 iridium Inorganic materials 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000010189 synthetic method Methods 0.000 description 6
- 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 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 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 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000010129 solution processing Methods 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- RQFMPANDXVSFMF-UHFFFAOYSA-N Fc(cc1)ccc1-c1c(-c(cc2)ccc2F)nc(cc(cc2)-c(cc3)ccc3-c(cc3)cc4c3nc(-c(cc3)ccc3F)c(-c(cc3)ccc3F)n4)c2n1 Chemical compound Fc(cc1)ccc1-c1c(-c(cc2)ccc2F)nc(cc(cc2)-c(cc3)ccc3-c(cc3)cc4c3nc(-c(cc3)ccc3F)c(-c(cc3)ccc3F)n4)c2n1 RQFMPANDXVSFMF-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
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- 229920006362 Teflon® Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052768 actinide Inorganic materials 0.000 description 2
- 150000001255 actinides Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 2
- 238000007646 gravure printing Methods 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 2
- 238000004776 molecular orbital Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000003921 oil Substances 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
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
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- 239000011148 porous material Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 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 2
- 238000007740 vapor deposition Methods 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- BODYVHJTUHHINQ-UHFFFAOYSA-N (4-boronophenyl)boronic acid Chemical compound OB(O)C1=CC=C(B(O)O)C=C1 BODYVHJTUHHINQ-UHFFFAOYSA-N 0.000 description 1
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 1
- SBHSHIFLFAKJNW-UHFFFAOYSA-N 2,6-ditert-butyl-4-methylaniline Chemical compound CC1=CC(C(C)(C)C)=C(N)C(C(C)(C)C)=C1 SBHSHIFLFAKJNW-UHFFFAOYSA-N 0.000 description 1
- UDGYLQTZGJGKPC-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-(trifluoromethyl)pyridine Chemical compound C1=CC(F)=CC=C1C1=CC=C(C(F)(F)F)C=N1 UDGYLQTZGJGKPC-UHFFFAOYSA-N 0.000 description 1
- XVKLMYQMVPHUPN-UHFFFAOYSA-N 2-bromoquinoxaline Chemical compound C1=CC=CC2=NC(Br)=CN=C21 XVKLMYQMVPHUPN-UHFFFAOYSA-N 0.000 description 1
- JFZJMSDDOOAOIV-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=C(Cl)N=C1 JFZJMSDDOOAOIV-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
- AXNUJYHFQHQZBE-UHFFFAOYSA-N 3-methylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N)=C1N AXNUJYHFQHQZBE-UHFFFAOYSA-N 0.000 description 1
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- 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
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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
- 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
- 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
- C07C211/52—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 the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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Description
200403229 玫、發明說明: 【相關申請案之前後參照】 本業係自美國臨時申請案序號60/394767號,2002年7月1〇 曰申睛’及美國臨時申請案序號60/458277號,2003年3月28 曰申請提出優先權申請。 【發明所屬之技術領域】 本發明係關於一種電荷傳送組合物。本發明進一步係關 於一種感光電子裝置,其中至少有一種包含該電荷傳送組 合物之活性層。 【先前技術】, 在有機感光電子裝置如構成0LED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。在〇LED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 伤曰經使用簡單有機分子、共輛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 走位於感光(例如,發光)層與接觸層之一之間。孔傳送層可 定位於感光層與孔發射接觸層之間,亦稱為陽極。電子傳 送層可足位於感光裝置内之感光層如有機金屬發光物質與 電子發射接觸層之間,亦稱為陰極。 對於電荷傳送物質及抗猝減物質有持續需要。 【發明内容】 86544 200403229
本發明係關於—储兩4/ A 、 種电何傳达組合物,其為喹噚啉衍生 物。1喹噚啉衍生物具有圖1所示之Si,其中:
Rl及R2在每次出現可為相同或不同並選自H、F、a、Br、 ^ 癸久基鉍基、甲矽烷基、矽氧基、烷基、雜 烷基、~基、块基、芳基、雜芳基、伸燒基芳基、 晞基芳基、炔基芳基、伸燒基雜芳基、稀基雜芳基、 、失基2居万基 CnHaFb、〇cnHaFb、c6HcFd及 OC6HcFd, 或R2二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+i,及&扣5, η為1至12之整數;及 ζ為0或1至4之整數。 在另一具體例中’本發明得關认
你關於一種具有圖2所示之式II 之電荷傳送組合物,其中: R1、R2、a至d及η定義如上, R在母次出現可為相同或不同 w 〜1丨』亚選自早鍵及一基團,選 自伸院基、雜伸燒基、伸#甘 v , 伸万基、雜伸芳基、伸芳基 伸烷基、及雜伸芳基伸焓其 甲基,伸炔基、伸決基伸芳 基、伸決基雜伸芳基。 Q選自單键及多價基; m為等於至少2之整數, P為0或1,及 X為0或1至3之整數。 在另一具體例中,本發明係關认 # Ώ >门 了關於一種具有圖3所示之Sin 之電荷傳送組合物,其中·· 86544 200403229 ^、R2、a《d、定義如上, R3在每次出現可為相同或 、 <丨』並選自早鍵及一基團,選 自伸烷基、雜伸垸基 ?万基、雜伸芳基、伸芳基 伸燒基、及雜伸芳基 土斤洗基,伸炔基、伸炔基伸芳 基、伸炔基雜伸芳基。 Q選自單鍵及多價基; m為等於至少2之整數;及 P為0或1。 在另一具體例中’本發明係關於一種電子裝置,具有至 層包含選自圖1至3所示之式卜η及m之物質,並中 本又所用之術語”電荷傳送組合物"意指可接收來自電極 〈電荷並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 U之%子傳送組合物可自陰極接收負電荷並傳送之。術 抗猝減組合物”意指—種物質,其可防止阻滯或消除能 里轉移及電子轉移自感光層之激發狀態至鄰接層。術語"感 光性”意指任何顯示電發冷光性、光致發冷光性及/或光敏性 之物貝。術浯HOMO"意指化合物之最高佔據的分子軌道。 術語"LUMO"意指化合物之最低佔據的分子軌道。術語"基 團”意指化合物之一部分,如有機化合物内之取代基。字首 Π雜’’意指一或多個碳原子用不同原子更換。術語,,燒基π意指 自具有一接附點之脂肪族烴衍生之基團,該基團可未經 取代或經取代。術語’’雜烷基,,意指一自具有至少一個雜原 86544 200403229 子及具有一接附點之脂肪族烴衍生之基團,該基團可未經 取代或經取代。術語”料基”意指—自脂肪族烴衍生並具 有二或多個接附點之基團。術語"雜·基”意指—自具有 至少-個雜原子之脂肪族烴衍生並具有:或多㈣附點之 基團。術語”締基”意指一自具有一或多個碳-碳雙鍵之煙衍 生並具有-接附點之基團,該基團可未經取代或經取代。 術語”炔基”意指一自具有一或多個碳_碳三鍵之烴衍生並且 有一接附點之基團,該基團可未經取代或經取代。術語"伸 締基”意指—自具有—或多㈣·碳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。術語” 伸块基"意指-自具有-或多個碳.碳三鍵之烴衍生並呈有 二或多個接附點之基團’該基團可未經取代或經取代。術 語,,雜稀基,,;”雜伸晞基”、,,雜块基”及"雜伸块基,|意指具 有-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瘦 取代。術語”雜芳基”意指—自具有至少一個雜原子並具有 -接附點之芳香族基衍生之基團,該基團可未經取代或經 :代:術語"芳基伸燒基”意指—自具有芳基取代基之燒基 何生《基團’孩基團可進一步未經取代或經取代。術語”雜 芳基伸燒基”意指—自具有雜芳基取代基之燒純生之基 團及基團可進一步未經取代或經取代。術語n伸芳基”音 指-自具有二接附點之芳香族煙衍生之基團,該基图可: 經取代或經取代。術語”雜伸芳基"意指一自具有至少一雜 原子並具有二接附點之芳香族基衍生之基團,該基團可未 86544 -9- 200403229 經取代或經取代。術語”伸芳基伸燒基,,意指一具有芳基與 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 基團。術語”雜伸芳基伸烷基”意指一具有芳基與烷基且在 芳基上具有一接附點而在烷基上具有一接附點之基團,且 其中具有至少一個雜原子。除非另予指明,所有基團皆可 未經取代或經取代。詞句”鄰接至”,當用以指明為裝置中 之層時,並非意指一層直接鄰接至另一層。另一方面,詞 句’’鄰接R基”,意指在化學式中互相鄰接之尺基(即,由键連 接 < 原子上之R基)。術語”化合物,,意指未充電物質,由進 一步由原子所組合之分子所構成,其中原子無法用物理手 段分離。術語”配位體”意指接附至金屬離子之配位區域之 分子、離子或原子。術語,,錯合物”,當用作名詞時,意指 具有至少一個金屬離子與至少一個配位體之化合物。術語 π聚合物”意指涵蓋低聚合物類並包括具有2或多個單體單 π <物質。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i至丨8 (化學與物理之c R c手冊,第8 i 版,2000) 〇 除非另予疋義,本文所用之所有技術與科學術語具有如 熟習本發明所屬技術之一般者共同了解之相同意義。除非 另予定義,圖式中所有字母符號代表原子及該原子縮寫。 雖然類似或等於本文所述之方法及物質可用於實施或試驗 本發明’但適當方法及物質說明如下。本文所述之所有刊 物、專利申請案、專利及其他參考物皆以引例整個併入。 在爭論情況下,本說明書包括定義將受控制。此外,物質、 86544 -10- 200403229 方法及實例僅為例示性而非限制性。 由以下之細郎說明及申睛專利範圍當可明白本發明之其 他特性及優點。 【實施方式】 由圖1所示之式I之喹嘮啉衍生物化合物特別可用作電子 傳送組合物及抗猝減劑。喹吟啉化合物亦可用作發光物質 之宿主。 通常’ η為一整數。在一具體例中,η為1至20之整數。在 一具體例中,η為1至12之整數。 在一具體例中,R1選自苯基晞基及苯基炔基,其可進一 步被取代。 在一具體例中,R1選自醋酸烷酯及芳基羰基,其可進一 步被取代。 在/具體例中,R1選自具有1至12個碳原子之烷基。 在/具體例中,R2選自苯基、經取代苯基、吡啶基、及 經取代说淀基。取代基可選自F、α、Br、羥基、竣基、談 基、f矽:k基、矽氧基、燒基、雜院基、晞基、決基、芳 基、雜芳基、伸烷基芳基、烯基芳基、決基芳基、伸烷基 雜芳基、烯基雜芳基、炔基雜芳基、CnHaFb、〇CnHaFb、 及 0C6HcFd。 在/具體例中,R2二者一起為雙伸芳基,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、Br、羥基、羧基、羰基、甲矽 烷基、矽氧基、垸基、雜烷基、婦基、炔基、芳基、雜芳 86544 -11 - 200403229 基、伸烷基芳基、缔基芳基、炔基芳基、伸烷基雜芳基、 · 晞基雜芳基、块基雜芳基、CnHaFb、0CnHaFb、及 OC6HcFd 〇 — 此類適當ET/AQ化合物之例包括但不限於圖4八至4人〇之 式1(a)至I(ag)所提供者。 由式I表示之組合物可使用標準合成有機技術製備,如實 · 例所示。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”溶液加工”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㈣冒 式。典型溶液加工技術包括,例如,溶液鑄製、滴液鑄製、 簾鑄製、旋塗、網目印刷、噴墨印刷、凹版印刷等。 · 在某些情況了,最好增加化合物之Tg以改良穩定性、可 塗性及其他特性。此可藉連接二或多種化合物與連接基一 起以形成圖2所示具有式η或圖3所示具有式m之化合物完 成。在此等式巾,Q可為單鍵或多價連接基,具有二或多個 ^附”’、占夕饧連接基可為具有二或多個接附點之烴基,並 嚷| 可為脂肪族或芳香族。多價連接基可為雜㈣基或雜伸芳 基其中4原子可為,例如,N、〇、S、或Si。多價連接基 Q〈例包括但不限於,伸燒基、伸晞基及伸決基、及具有雜· =子:類似化合物;單、多環及溶合環芳香族化合物及雜 :曰秩化合物,芳基胺,如三芳基胺;石夕燒及石夕氧燒。多 I接基Q之附加例提供於圖5之式v(a)至乂作)。在式π⑴ §任何妷皆可連接至電荷傳送部份。在式IV(h)中,任何 原子白可連接至電荷傳送部份。亦可使用雜原子如&及 86544 -12- 200403229
Sn。連接基亦可為-[SlMeRLSiMeRl]n•,其中Rl&n定義如 通常,m為至少等於2之整數。實際數目端視卩上之可得 連接位置數目及三芳基甲烷與(^之幾何而定。在一具體例 中,m為2至10之整數。 在一具體例中’在式π中,選自苯基及經取代苯基。取 代基可選自F、a、Br、烷基、雜烷基、缔基、及块基。 在一具體例中,在式II中,選自醋酸烷酯及芳基羰基, 其可進一步被取代。 在一具體例中,在式II中,Ri選自具有丨至12個碳原子之 燒基。 在一具體例中,在式II中,R2選自苯基、經取代苯基、吡 哫基、及經取代吡啶基。取代基可選自F、C1、Br、羥基、 羧基、羰基、甲矽烷基、矽氧基、烷基、雜烷基、缔基、 炔基、方基、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、块基雜芳基、、 〇CnHaFb、C6HcFd及 〇C6HcFd。 在一具體例中,在式II中,R2二者一起為雙伸芳基,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、C1、Br、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 雉方基、烯基雜芳基、炔基雜芳基、CnHaFb、〇CnHaFb、C6HeFd 及 OC6HcFd。 -13- /21 86544 200403229 在一具體例中,在式II中,χ為0。 在一具體例中,在式II中,R3選自芳基、雜芳基、烷基、 及雜燒基。在一具體例中,在式II中,R3選自苯基及經取代 苯基。在一具體例中,在式II中,R3選自具有1至12個碳原 子之烷基及雜烷基,其可進一步被取代。 在一具體例中,在式m中,r1選自苯基烯基及苯基炔基, 其可進一步被取代。 在一具體例中,在式III中,R1選自醋酸烷酯及芳基羰基, 其可進一步被取代。 在一具體例中,在式III中,R1選自具有1至12個碳原子之 烷基。 在一具體例中,在式ΠΙ中,R2為Η。 在一具體例中,在式m中,R3選自芳基、雜芳基、烷基、 及雜烷基。在一具體例中,在式III中,R3選自苯基及經取 代苯基。在一具體例中,在式m中,R3選自具有1至12個碳 原子 < 烷基及雜烷基,其可進一步被取代。 具有式II之連接化合物之特定例提供於圖6人至AI中之式 11(a)至 11(1)。 電子裝f 本發明亦關於一種電子裝置,包含至少一種定位於感光 層Μ私極間之本發明之電荷傳送組合物。典型裝置結構 不於圖8。裝置100具有陽極層110及陰極層160。包含孔傳 运物貝之層120鄰接陽極。包含電子傳送及/或抗猝減物質 之層140(’ET/AQ’’)鄰接陰極。感光層13〇在孔傳送層與電子 722 86544 -14 - 200403229 傳送及/或抗猝減層之間。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100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,其回應輻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 φ 電池,該等術語敘述於Markus,John,Electronics and Nucleonics Dictionary,470 and 476(McGraw-Hill,Inc_ 1966)。 本發明之p奎吟琳衍生物化合物特別可用作層140内之電 ., 子傳送及/或抗猝減組合物,或作為層150内之電子傳送組 · 合物。例如,在一具體例中,本發明之p奎P号淋衍生物化合 物可用作發光二極體内之電子傳送及/或抗猝減層。 亦須知ET/AQ物質必須與所用之感光物質在化學上相 容。例如,ET/AQ物質當沉積在感光物質層上時必須形成 · 平滑膜。若聚結發生時,裝置之性能會惡化。 裝置之其他層可由任何已知用於該層之物質製得。陽極 110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 物如錮-錫氧化物。陽極110亦可包含有機物質如聚苯胺, -15- 7)¾ 86544 200403229 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ΐ· 357, pp 477_479 (1992年 6 月 11 日)。陽極與陰極 中至少一個應至少局部透明以容許看到一般光線。 - 可用於層120之孔傳送物質之例概述於,例如,
Kirk-Othmer Encyclopedia of Chemical Technology,第四版, V〇l· 18, p. 83 7-860, 1996, Y_ 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 k 苯基)-[1,1’-二苯基]-4,4’-二胺(TPD)、1,1-雙[(二-4-甲苯胺基)_ 苯基]%己烷(TAPC)、N,N’-雙(4_甲基苯基)_Ν,Ν,^ (4•乙基 私基)[1,1 -(3,3 - 一甲基)二苯基]_4,4’_二胺(ETPD)、肆-(3_ 甲基苯基卜沭队^一义伸苯二胺^^入^卜苯基-心^…二_ 苯基胺基苯乙烯(TPS)、對_(二乙基胺基)苄醛二苯基腙 (DEH)、三苯胺(TPA)、雙[4+Ν,Ν_二乙基胺基)_2_甲基苯 基](4-甲基苯基)甲燒(MPMP)、L苯基冬[對仁乙基胺基) 苯、希基]5*"[對-(一乙基胺基)苯基]Ρ比吐琳(PPR或 DEASP}、1,2_反式_雙(紐_卡巴唑冬基,環丁燒⑴、書 Ν,Ν,Ν’,Ν’-肆(4-甲基苯基)-〇51,·二苯基 Μ,4,_ 二胺(ΤΤΒ)、及 哺琳化—合物如銅酜菁。共用的孔傳送聚合物為聚乙締卡巴· 坐(苯基甲基)水矽烷及聚苯胺及其混合物。亦可藉摻雜上 述孔傳送分子進入聚合物如聚苯乙烯及聚破酸酉旨内而得孔 傳送聚合物。 感光層130〈例包括所有已知電發冷光物質。以有機金屬 ^ ~光化合物較佳。最佳化合物包括環金屬化錶及銘電 發冷光化合物及其混合物。銥與苯基吡啶 、苯基ρ奎琳、或
86544 -16- 200403229 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WO 02/02714號。其他有機金 屬錯合物敘述於,例如,公告申請案美國專利2001/0019782 號、歐洲專利1191612號、WO 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)之電發冷光裝置敘述於Burrows and Thompson於公告 PCT申請案WO 00/70655號及WO 01/41512號。包含電荷負 載宿主物質及發磷光鉑錯合物之電發冷光發射層敘述於, Thompson等人,美國專利 6,303,238號,Bradley等人,於 Synth· Met. (2001),116(1-3),379-383,及 Campbell 等人,於 Phys· Rev. B,Vol· 65 085210,如一些適當銀錯合物之例提供於圖 7Α至7Ε,如式VI(a)至VI(e)。亦可使用類似配位基鉑錯合 物。此等電發冷光錯合物可單獨使用,或如上述掺雜入電 荷負載宿主内。本發明之p奎崎琳物質亦可作為發射層内之 該電荷負載宿主。 陰極160為一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或非金 屬。陰極用之物質可選自族1之鹼金屬(如Li,Cs)、族2(鹼 土)金屬、族12金屬,包括稀土元素及鑭系元素及锕系元 素。可使用物質如鋁、銦、鈣、鋇、釤及鎂及其組合。含 Li有機金屬化合物,LiF及Li20亦可沉積在有機層與陰極層 之間以降低操作電壓。 已知在有機電子裝置内具有其他層。例如,在陽極110與 孔傳送層120之間可具有一層(圖未示)以利正電荷傳送及/ 86544 -17- 200403229 或層4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,某些或 所有1¼極層110、孔傳送層120、電子傳送層140及150及陰 — 極層160可被表面處理以增加電荷載體傳送效率。對各成份 層物質之選擇最好由平衡提供具有高裝置效率及裝置操作 壽命之裝置之目標決定。 . 須知各官能層可由超過一層所構成。 . 裝置可藉各種技術,包括按序蒸汽沉積個別層在適當基 __ 材上製備。可使用基材如玻璃及聚合膜。可使用傳統汽相 沉積技街如熱蒸發、化學汽相沉積等。或者,有機層可使 用任何傳統塗佈或印刷技術,包括但不限於旋塗、浸塗、 輥-輥技術、噴墨印刷、凹版印刷、及網目印刷自溶液或分 散液於適當溶劑内塗佈。通常,不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12〇, 50 2000i矢,車乂佳為20040Q0埃;感光層丨3〇,ι〇·2〇〇〇埃, 較佳為100-1000埃;電子傳送層14〇及15〇,5〇_2〇〇〇埃,較 嚷| 佳為100-1〇〇〇埃,陰極16〇,2〇〇1〇〇〇〇埃,較佳為3〇〇5〇训 埃。電子-孔再組合區域於裝置内之位置,因而裝置之發射 光譜可被各層之相對厚度影響。因此,應選擇電子-傳送層 · <厚度,使得電子-孔再組合區域在發光層内。層厚度之所 名乂比率端視所用物質之實際性質而定。 本發明《喹嘮啉衍生物化合物可用於〇LEDs以外之應 用例如,此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 86544 -18- 200403229 驅動器應用。 下列實例例示本發明之某種特性及優點。預定其為本發 — 明之例示性而非限制性。除非另予指明,所有百分比皆依 重量計。 1-16 · 此等實例例示喹呤啉衍生物ET/AQ組合物之製備。 私 貫例1 此實例例示圖4N之化合物I(n)之製備。 2,3-(二-4-氟苯基)-6·溴喹嘮啉(2·〇〇克,5.00毫莫耳)、對-第三丁基苯乙烯(1.02克,6.40毫莫耳)、Na2CO3(0.68克,6.40 · 毫莫耳)、反式-二(μ-醋酸基)雙[〇-(二-鄰甲苯基_膦基)苄基] _ 二飽(II) (0.020克’ 0.02¾莫耳)及2,6-二-第三丁基-對甲酉分 (0.5 52克,2.50¾莫耳)與n,N-二甲基醋酸醯胺(12毫升)裝入 爐乾燥可釋放Schlenk燒瓶内。Schlenk燒瓶用鐵氟龍閥密 閉’反應混合物在130°C下加熱21小時。所得混合物冷卻至 _ 室溫、在Et2〇(230毫升)内稀釋並透過矽墊過濾。過滤物用 水(2x100^:升)及鹽水(1x50^:升)洗滌。乾燥有機層並濃縮 以得粗產物,然後,其係藉閃蒸層析術純化以得72%(丨·7 i · 克)產率之淡黃色固體之純產物。19F CD2ei2)· δ-113·48及-113.58。 實例2 此實例例示圖40之化合物1(〇)之製備。 心氟苯基乙炔(0.334克,2.78毫莫耳)、2,3-(二_4_氣苯 86544 -19- 200403229 基)-6-溴喹噚啉(1 克,2.53 毫莫耳)、Pd2(dba)3(0_046克,0.05 毫莫耳)、三苯膦(0.066克,0.253毫莫耳)、Cul(0.010克,0·05 晕莫耳)及三乙胺(15毫升)裝入爐乾燥可釋放schlenk燒瓶 内。然後金閉此燒瓶並在60。〇下加熱24小時。所得混合物 用CHWl2稀釋、用HA及鹽水洗滌、經MgS04乾燥、過濾並 濃縮以得灰白色固體。粗產物係藉己烷(3χ2〇毫升)重複洗滌 純化以得 0.924克(84%產率)。4 NMR(CD2C12,500 ΜΗζ) δ 8.37 (d,1Η,J=1.6),8.20-8.18 (d,1Η,8.8),7.98-7.95 (dd,1Η, J=8.3, 1.5),7.74-7.70 (dd,2H,J=5.4, 3.6),7.64-7.60 (m,4H), 7.24-7.14 (m,6H)。19F NMR(CD2C12, 500 MHz) δ -111.14 (m, 1F),-113.1 (m,2F)。 實例3 此實例例示圖4Q之化合物I(q)之製備。 實例1之化合物1(11)(1.70克,3.55毫莫耳)、£3〇八11140?(1/€ 觸媒(0.056克)及MeOH(45毫升)裝入反應器内。反應混合物 係用氮氣沖洗、加壓至500 psig H2並加熱至60。(:歷8小時。 揮發物在真空下除去’產物係藉閃蒸層析術(5%Et〇At/己燒, 其中nEt’’表示乙基及flOAcn表示醋酸酯)純化以得淡黃色粉 (0.220克,13%)。19F NMR (376.8Hz,CD2C12)J -111.14及 -114.60 〇 實例4 此實例例示圖4B之化合物1(b)之製備。 3,4-二胺基甲苯(28·78克,.236莫耳)與苯偶醯(45克,.214 莫耳)之混合物於738¾升氯仿内與2.16毫升三氟醋酸回流3 86544 -20- 200403229 小時。混合物用10%HC1、鹽水洗滌3次、並經MgS〇4乾燥、 · 過濾、然後透過矽墊用真空過濾。所得熔液蒸發至乾燥狀 怨。自550毫升甲醇再晶化69克粗產物。過濾的固體在5〇〇c — 下於真芝爐内乾燥1小時以得5 5 _ 5 6克乾燥固體。7 8 · 8 %產率。 實例5 此實例例示圖4E之化合物I(e)之製備。 , 3.4- 一胺基甲苯(4.49克,.037莫耳)與4,4,-二甲氧基苯偶 · 醯(9.46克,.035莫耳)之混合物於125毫升氯仿内與〇·35毫升 _ 三氟醋酸回流6小時。混合物用水洗滌2次、並經MgS〇4乾 燥、並蒸發至〜11克。固體溶解於i ·· 1醋酸乙酯:氯仿内供 閃悉層析並用醋酸乙酯洗提。蒸發至9·7克深色固體。72% ^ 產率。 . 實例6 此實例例示圖4C之化合物1(c)之製備。 3.4- 二胺基甲苯(〇.603克,4.93莫耳)與1,1〇_二氮雜菲-5,6- 二酮(0.945克,4.50毫莫耳)之混合物於6〇2毫升氯仿内與 ϋ 0·35毫升三氟醋酸回流6小時。混合物透過介質燒料加熱過 一 滤以在乾燥後獲仔0 _ 8 5克淡黃色固體。產率6 3 %。 在冷卻後自母液可得第二產量以得另外〇·3丨克。 實例7 此實例例示圖4D之化合物1(d)之製備。 3.4- 二胺基甲苯(5.36克,44毫莫耳)與二氮雜菲喹諾酮 (8.33克’ .040莫耳)之混合物於119毫升氯仿内與〇·4毫升三 氟醋酸回流6小時。混合物透過介質燒料過滤並自43〇克甲 86544 -21 - 200403229 基乙基S同以仔5 · 5克鬆軟毛狀黃色產物。46%產率。 實例8 此實例例示圖4F之化合物1(f)之製備。 3.4- 二胺基甲苯(5.36克,44毫莫耳)與2,2,-吡啶(8.49克, 40¾莫耳)之混合物於119毫升氯仿内與〇·4毫升三氟醋酸回 流4小時。分離反應混合物並用1 〇〇毫升水洗滌4次、並蒸發 至10.4克。所得固體溶解於1 : 1醋酸乙酯:氯仿内供閃蒸層 析並用醋酸乙酯洗提。蒸發至9.3克固體。 實例9 此實例例示圖4G之化合物1(g)之製備。 3.4- 一胺基冬甲故甲酉旨(7.28克,44毫莫耳)與苯偶酸(8·41 克’ 40毫莫耳)之混合物於140毫升二氯甲烷内回流2丨小 時。反應混合物蒸發至乾燥狀態,然後在回流下溶解於52〇 毫升甲醇及150毫升二氯甲烷内。然後局部蒸發溶液以選擇 性晶化所欲產物。 實例10 此實例例示圖4κ之化合物I(k)之製備。 3,4-一胺基麥甲甲酉旨(6.37克’ .038莫耳)與4,4,_二甲氧 基本偶驗(9·46克,.035莫耳)之混合物於M2毫升二氯甲院内 與3滴三氟醋酸回流5小時。加入10.7克N-甲基吡咯烷酮並持 續回流26小時以上。混合物用水洗滌3次、經MgS〇4乾燥、 過濾及沉澱產物,以將有機溶液傾析入55〇克甲醇内。在靜 置隔夜後,過濾產物並在95°C下真空乾燥以得1〇·39克產物。 實例11 -22-
?38, 86544 200403229 此實例例示圖4R之化合物I⑴之製備。 · 3,4-二胺基苯甲酸甲醋(6.12克,.037莫耳)與二氮雜菲喹 諾酮(7_08克’ .034莫耳)之混合物於119毫升二氯甲燒内回 流。加入1〇〇克^曱基吡咯烷酮並將氯化溶劑蒸餾出。將罐 加溫至150°C,藉此可得透明溶液,反應藉氣體層析術跟 蹤。產物係藉澆入410克甲醇沉澱並將沉澱的固體過滤出。 · 產物係自甲苯再晶化,然後再自甲基乙基酮12〇〇克、甲苯 . 150克及四氫吱喃1100克之組合再晶化。產率為3·3克珍珠狀 _ 金色毛狀物質。 實例12 此實例例示圖4L之化合物1(1)之製備。 1,2-伸苯二胺(13.91克,0.129莫耳)與4,4,-二溴苯偶醯(45
克,0.116莫耳)之混合物於558毫升氯仿内與ι·〇毫升三氟醋 酸回流6小時。混合物用10% HC1洗滌3次並蒸發至〜51克。 在回流下用100毫升甲醇自600毫升醋酸乙酯再晶化。大型 晶體隔夜形成、過濾及用甲醇洗滌二次並乾燥至29·63克以 及4.9克自冷卻母液之第二產量。 實例13 此實例例示圖4Η之化合物1(h)之製備。 2,3-二胺基甲苯(4·84克,.040莫耳)與苯偶醯(7.56克,0.036 莫耳)之混合物於112毫升二氯甲燒内回流19小時。混合物 用12% HC1洗滌4次、經MgSCU、過滤並蒸發至〜9.5克棕色 固體。固體在回流下溶解於495克甲醇内,.然後將〜3〇〇克 溶劑蒸餾出。用冰冷卻以得良好晶體。過濾並用甲醇洗滌 86544 -23- 200403229 結晶餅。 實例14 此實例例示圖4(1)之化合物i(i)之製備。 — 2.3- 二胺基苯甲酸甲酯(5·05克,0·041莫耳)與二氮雜菲喹 諾酮(7·84克,0.038莫耳)之混合物於112毫升氯仿内回流” 小時。所得溶液用氯仿洗提物向下層析矽柱。自溶劑笑發 · 產物以在真空爐乾燥纟ij獲得約1 〇克。物質出現結晶。 實例15 赢 此實例例示圖4(J)之化合物Rj)之製備。 3.4- 二胺基苯甲酸甲酯(7·28克,0·044莫耳)與2,2,_峨淀 (8.48克’ 0·040莫耳)之混合物於14〇毫升二氯甲烷内回流7 、, 小時。溶液瘵發至15·7克,固體在回流下溶解於240毫升二 -氯甲烷及140毫升甲醇内。在加入28〇毫升甲醇及蒸發〜15〇 毫升溶劑後,將溶液靜置隔夜。收集所得固體並乾燥至9.8 克。取出7·7克物質並解於203克甲醇及5〇克二氯甲烷内。蒸 餾出>50毫升溶劑。晶體隔夜形成。過濾並在真空爐内乾燥。 實例16 此實例例示圖4Τ之化合物I⑴之製備。 2’3_( —_4_氟冬基)-6•溴ρ奎巧琳(1.23克,3.08毫莫耳)、1,3_ 二乙埽基四甲基矽氧烷(3·4〇毫升,丨4·8毫莫耳)、K〇ac(〇.440 克,4.48 毫莫耳)、Pd(〇Ac)2(〇〇12 克,〇〇6 毫莫耳)、ρ(〇_τ〇1)3 (0.06克’ 〇·2〇毫莫耳)、NEt3(〇 3〇〇毫升)、DMF(〜2毫升)及 水(〇.45毫升)裝入爐乾燥可釋放Schlenk燒瓶内。Schlen]^ 鐵氟龍閥密閉,反應混合物在95 X:下加熱48小時。所 86544 -24- 200403229 得混合物冷卻至室溫、在水(15毫升)内稀釋及產物用 CH2C12(15毫升)萃取。乾燥有機層並濃縮以得粗產物,其係 藉閃蒸層析術純化(3% EtOAc/己烷)以得(0.478克,31%產率) 之淡黃色固體。19F NMR(376.8Hz,CD2C12)·· 5 -113.45(br m)。 實例17-19 此實例例示具有超過一個喹吟啉基之電荷傳送組合物之 製備。
此實例例示圖6E之化合物11(e)之製備。 1,4-伸苯基雙硼酸(2克,12.1毫莫耳)、2,3-(二-4-氟苯 基)-6-溴喹噚啉(9.54 克,24.1 毫莫耳)、Pd(PPh3)4(2.78 克, ^ 2.41毫莫耳)、碳酸鉀(6.67克,48.3毫莫耳)、DME( 150毫升) . 及H2〇( 150毫升)裝入設有氮氣入口及冷凝器之3頸式500毫 升圓底燒瓶。將反應混合物回流24小時,然後用h20及 CHeh稀釋。有機層含有沉澱物,其係藉過濾單離並用 CH2C12洗开条以得2.75克(32%產率)灰白色粉。1η NMR _ (CD2C12, 500 MHz) δ 8.56-8.55 (m5 2Η),8·35-8·33 (d,2Η), 8.29 (m,2Η),8.12 (s,4Η),7·68-7_64 (m5 8Η),7.29-7.16 (m, 8H)。19F NMR(CD2C12, 500 MHz) δ -113.35 (m,2F)。 · 實例18 此實例例示圖6K之化合物II(k)之製備。 1,4-雙苯偶驢(1克,2.92毫莫耳)及4,5-二甲基-i,2-伸苯二 胺(〇·769克’ 5.84¾莫耳)於氯仿(20毫升)内之混合物在氮氣 環境下回流15小時。將己烷加入反應混合物内,沉澱出淡 86544 -25- 200403229 男色〉儿殿物,其係藉過濾單離並用己烷洗滌以得淡黃色粉 · 之產物(1.32 克,83% 產率)。4 NMR(CD2Cl2, $⑻ ΜΗζ:) δ 7.89-7.88 (d,4Η,J=7.1 Ηζ),7.50-7.48 (dd,4Η,J=1.5 Ηζ,7·7 〜 Ηζ),7.45 (s,4Η),7.35-7.31 (m5 1〇η)5 2.53 (s,12Η)。 實例19 此實例例示圖6A之化合物11(a)之製備。 . 3,3 - 一胺基聯苯胺(0.4580克,2.14毫莫耳)與ι,ι〇_二氮雜 菲5,6- 一酉同(0.9458克’4.5¾莫耳)之混合物於1〇克甲基p比 洛燒嗣與0.045毫升三氟醋酸内在85°C下加熱23小時。在周 圍溫度下,將氯仿加入罐内,内含物透過細緻燒料過濾並 用丙酮及二乙醚洗滌,然後在9〇°C及真空下乾燥。 - 實例20 , 此實例例示圖4M之化合物I(m)之製備。 根據用於製備1(〇)之合成法實施此化合物之合成以得 58%產率之所欲產物。1HNMR(CD2C12, 500 ΜΗζ) δ 8.38 (d, 1H,J=1.8 Hz),8.20-8.18 (d,1H,8·4 Hz),7.99-7.97 (dd,1Η, _ J=1.8 Hz,8.7 Hz),7.73-7.71 (m,2H),7.64-7.61 (m,4H), 7.52-7.50 (m,3H),7.19-7.14 (m,4H)。19F NMR(CD2C12, 500 MHz) δ -113.14 (m,2F)。 實例21 此實例例示圖6G之化合物11(g)之製備。 根據用於製備11(e)之合成法實施此化合物之合成以得 13°/。產率之所欲產物。iH NMR(CD2C12, 500 ΜΗζ) δ 8.42-8.41 (d,2Η,J=1.9),8.20-8.18 (d5 2Η,J=8.5),8.13-8.11 (dd,2Η, 86544 -26- 200403229 J=9.1 Hz,2.0 Hz),8.00 (s,4H),7.54-7.51 (dd,8H,J=8.7 Hz, 3.1 Hz),6.9-6.9 (q,8H),5·48 (s,12H)。 實例22 此實例例示圖6D之化合物11(d)之製備。 根據用於製備11(e)之合成法實施此化合物之合成以得 10%產率之所欲產物。1H NMR(CD2C12, 500 ΜΗζ) δ 8.62-8.61 (d,2Η,J二 1.5),8·44-8·41 (m,4Η),8.41-8.39 (d,2Η,J=9.5 Hz), 8.34-8.31 (dd,2H,J-8.3 Hz,1.6 Hz),8.14 (m,6H),8.12-8.11 (m,2H),7.98-7.94 (m,4H),7.38-7.34 (m,4H)。 實例23 此實例例示圖6K之化合物II(k)之製備。 根據用於製備II(j)之合成法實施此化合物之合成以得 66%產率之所欲產物。iH NMR(CD2C12, 500 ΜΗζ) δ 8.09_8.06 (t,2Η,J=7.4 Ηζ),7·98-7·96 (d,2Η,J=7.2 Ηζ),7·69·7·67 (d, 2Η,8.9),7.59-7.51 (m,10Η),7.43-7.40 (m,8Η),2.67 (s,6Η)。 實例24 此實例例示圖6L之化合物11(1)之製備。 根據用於製備II(j)之合成法實施此化合物之合成以得 650/。產率之所欲產物。iH NMR(CD2C12, 500 ΜΗζ) δ 8.29-8.24 (m,1Η),8.07-8.01 (m,1Η),7.90-7.86 (m,1Η),7·80-7·78 (m, 0.6H),7.72-7.66 (m,1H),7.64-7.59 (m,4H),7.51-7.44 (m, 3H)。19F NMR(CD2C12, 500 MHz) δ -108.4 (m,2F),-108.9 (m5 3F),·109·2 (m5 8F),-109.4 (m,8F)。 實例25
86544 -27- 200403229 此實例例示圖6M之化合物II(m)之製備。 使用卞系之合成圖式貫施此化合物之合成。
Br
Br
F f
使用以1(0)於製造65%產率之預期產物之合成法可得化 合物 Il(ma)。4 NMR(CD2C12, 500 ΜΗζ) δ 7.64-7.60 (m,4H), 7.27 (s,2Η), 7.20-7.16 (t,4Η,J=8.9 Hz)。19F NMR(CD2C12, 500 MHz) δ -110.10 (m5 2F)。在氮氣下,將 II(ma)(2.00 克, 6·25 毫莫耳,0· 1 當量)、Adogen 464(0.125 克)、過鐘酸 _ (4·9 克,31.25毫莫耳,5.00當量)、碳酸氫鈉(1.05克,12.5毫莫 耳,2.0當量)、Η2Ο(80毫升)及CH2C12(50毫升)裝入設有冷凝 器之3頸式圓底燒瓶。將混合物回流36小時。在冷卻至室溫 後’將9.3克碳酸氫鈉與4毫升HC1缓慢加入反應混合物内以 中和並除去任何多餘氧化劑。然後,反應混合物用二氯甲 燒及HA稀釋、分離層、有機部份用h2〇、鹽水洗滌並經 MgS〇4乾燥。產物係藉蒸發溶劑,然後自乙醇再晶化以得 86544 -28 - 200403229
0·6克(25%產率)黃色針狀晶體之II(mb)。4 NMR(CD2C12, 500 MHz) δ 8.25-8.21 (dd,4H,J=8.9 Hz,5.6 Hz),7.98 (s,2H), 7.36-7.32 (t,4H,J=8.70 Hz)。19F NMR(CD2C12, 500 MHz) δ -101.8 (m,2F)。根據用於製備II(k)之程序實施化合物II(m) 之合成以得20%產率之所欲產物。1H NMR(CD2C12, 500 MHz) δ 8.25-8.21 (m,1H),8.19-8.15 (m,1H),7.85-7.78 (m,2H), 7.73-7.64 (m,6H),7.29-7.25 (t,4H),6·69-6·66 (m,2H)。19F NMR(CD2C12, 500 MHz) δ -108.7, -108.8 (m,2F),-112.4 (m, 1F),-112.6 (m,IF) 〇 電子傳送及/或抗猝減組合物之特性概述於下表1。 表1 特性 化合物 吸收開始 吸收最大 E12 對 SCE LUMO 對 (nm),E1-E5 量(nm) (伏), 真空(eV),El 化合物I⑻ 375 345 -1.5 -3.33 化合物1(b) 378 339 -1.6 -3.24 化合物1(c) 400 385 -1.17 -3.67 化合物1(d) 410 397 1.3 -3.54 化合物1(g) 390 352 -1.29 -3.55 化合物11(a) 一- --此線之目的為何? 化合物1(e) 405 369 -1.66 -3.18 化合物1(f) 378 339 -1.53 -3.31 化合物1(〇) 420 382 -1.35 -3.49 化合物1(1) 407 394 -1.28 -3.56 -29- 7 <7 86544 200403229 化合物I(k) 385 343 -1.59 -3.25 化合物I(w) 417 401 -1.03 -3.81 化合物I(p) 380 347 -1.49 -3.35 化合物I(x) 380 342 -1.22 -3.62 化合物A 368 310 -1.85 -2.99 DDPA 化合物B 366 316 -1.95 -2.89 DPA 實例27 此實例例示銥電發冷光錯合物之製備,如圖7A之式V(a) 所示。 笨基吡啶配位體,2-(4-氟笨基V5-三氟甲基吡啶 所用之一般程序敘述於0. Lohse, P. Thevenin,E. Waldvogel Synlett,1999, 45-48。將 200 毫升脫氣水、20 克碳 酸钾、150毫升1,2-二甲氧基乙烷、0.5克Pd(PPh3)4、0.05莫 耳2-氯-5-三氟甲基吡啶及0.05莫耳4-氟苯基硼酸之混合物 回流(80-90°C )16-30小時。所得反應混合物用300毫升水及 用CH2C12(2x100毫升)萃取。組合有機層經MgS04乾燥,溶 劑藉真空除去。液態產物係藉分餾真空蒸餾純化。固體物 質係自己烷再晶化。經單離物質之典型純度為>98%。 銥錯合物 當溫度缓慢(30分鐘)升至185°C (油浴)時,在N2之流動 下,強力攪拌IrCl3 · nH20(54% Ir ; 508毫克)、上述2-(4-氟 苯基)-5-三氟甲基吡啶(2.20克)、Ag〇COCF3(1.01克)及水(1 86544 -30- 200403229 毫升)之混合物。在185-190°C下2小時後,混合物固化。混 合物冷卻至室溫。固體用二氯甲烷萃取,直到萃取物脫色 為止。組合的二氯f7烷透過短矽柱過濾並蒸發。在甲醇(50 毫升)加入殘餘物後,燒瓶保持在-10°C下隔夜。分離參-環 狀金屬化錯合物,圖7A中之化合物V(a)之黃色沉澱物、用 甲醇洗滌、及在真空下乾燥。產率:1.07克(82%)。錯合物 之X射線品質晶體係藉緩慢冷卻其加溫溶液於1,2-二氯乙 燒内而得。 實例28 此實例例示OLEDs使用本發明之電荷傳送組合物之形 成。 包含孔傳送層(HT層)、電發冷光層(EL層)及至少一層電 子傳送及/或抗猝減層(ET/AQ層)之薄膜OLED裝置係藉熱 蒸發技術製造。使用具有油擴散泵之Edward Auto 306蒸發 器。所有薄膜沉積之基本真空範圍為10·6托爾。沉積室可沉 積五種不同之薄膜而不需停止真空。 使用獲自Thin Film Device公司之帶紋氧化錫銦(ITO)塗 佈之玻璃基材。此等ITO’s以塗有1400埃ITO塗料並具有片 材電阻為30歐姆/平方及80%光傳輸率之Corning 1737玻璃 為基礎。然後帶紋ITO基材於清潔劑水溶液内以超音波方式 清潔。然後,基材用蒸餾水、接著異丙醇清洗、然後於甲 苯蒸汽内脫氣〜3小時。 然後,清潔過帶紋ITO基材裝入真空室内而此室向下泵抽 至10_6托爾。進一步使用氧電漿清潔基材約5-10分鐘。在清 86544 •31 - 200403229 潔後,多層薄膜藉熱蒸發按序沉積在基材上。最後,A1或 LiF與A1之帶紋金屬電極透過罩沉積。在沉積期間,使用石 英晶體監視器(Sycon STC-200)測定薄膜厚度。實例中記載 之所有薄膜厚度皆為標稱,假定沉積物質之密度欲為一種 計算。然後,自真空室取出完成之OLED裝置並直接特性化 而不用包膠。 表2概示用本發明之喹呤啉衍生物ET/AQ組合物製成之 裝置。在所有情況下,陽極為ITO,如上所述,孔傳送層為 MPMP,及發射層為具有所示厚度之實例27之銥錯合物。當 呈現時,電子俸送層150為具有規定厚度之參(8-羥基喹諾基) 鋁(III),Alq。陰極為具有規定厚度之A1層或LiF/Al雙層。 表2 裝置 樣品 ht(A) EL, A ET/AQ,A ET,A 陰極,A 比較例A 507 407 化合物A 408 A1721 比較例B 507 405 化合物B 407 A1 732 3-1 545 403 1(a) 430 Alq 430 A1737 3-2 508 625 1(b) 425 A1 732 3-3 509 413 1(c) 416 A1 750 86544 -32- 200403229 3-4 578 411 1(d) 381 A1711 3-5 527 418 1(e) 418 A11027 3-6 535 415 i(f) 459 A11039 3-7 549 425 1(g) 423 A11023 3-8 510 445 II⑻ 415 A1710 3-9 502 403 i(f) 106 Alq 303 LiF5 A1470 3-10 502 402 1(d) 102 Alq 303 LiF5 A1497 3-11 501 402 1(c) 103 Alq 302 LiF5 A1 111 3-12 513 409 1(h) 414 A1718 3-13 514 416 I(i) 408 A1718 3-14 515 500 1(0 410 A1 729 3-15 504 488 ι〇·) 402 A1721 3-16 505 412 I(k) 439 A1 727 86544 -33- 200403229 3-17 516 409 1(1) 432 A1733 3-18 302 403 11(c) Alq 302 LiF 10 102 A1 452 3-19 304 402 11(d) Alq 302 LiF 10 101 A1 452 3-20 305 404 11(e) Alq 303 LiF 10 102 A1 454 3-21 301 402 Π(ί) Alq 305 LiF 10 105 A1451 3-22 303 406 I⑽ Alq 302 LiF 10 103 A1 453 3-23 303 405 n(g) Alq 305 LiF 10 102 A1453 3-24 304 402 I⑻ Alq 303 LiF 10 101 A1453 3-25 303 410 11(h) Alq 305 LiF 10 102 A1453 3-26 306 404 I(〇) Alq 302 LiF 10 103 A1 453 3-27 305 404 II(i) Alq 305 LiF 10 192 A1 453 3-28 303 402 I(P) Alq 304 LiF 10 102 A1456 3-29 303 403 Πϋ) Alq 303 LiF 10 103 A1335 86544 -34- 200403229 3-30 303 405 II(k) Alq 305 LiF 10 102 A1 284 3-31 303 405 11(1) 102 Alq 303 LiF 10 A1 232 OLED樣品係藉測定其⑴電流-電壓(I - V)曲線,(2)電發冷 光輻射對電壓,及(3)電發冷光光譜對電壓特性化。所用之 裝置200顯示於圖9。OLED樣品220之Ι-V曲線係用Keithley 源-測量單元型號237, 280測定。電發冷光輻射(單元為cd/m2) 對電壓係用Minolta LS-110發冷光量尺210測定,而電壓則 使用Keithley SMU掃描。電發冷光光譜係使用一對透鏡 230,透過電子遮光器240,透過光譜儀250分散而收集光, 然後用二極管列陣檢測器260測定。所有三種測定皆同時進 行並由電腦270控制。裝置在某種電壓下之效率係藉LED之 電發冷光輻射除以進行裝置所需之電流密度測定。單元為 cd/A 〇 使用本發明之喹嘮啉衍生物ET/AQ組合物之裝置之結果 示於下表3 : 表3 裝置之電發冷光性 樣品 尖峰輻射 cd/m2 在尖峰輻射下 之效率cd/A 尖峰效率, cd/A 尖辛功率 效率Im/W 化合物F 3000 在22 V 10 14 化合物G 4500 在19V 10 20 -35- ?4 3 86544 200403229 表3 裝置之電發冷光性 樣品 尖峰輻射 cd/m2 在尖峰輻射下 之效率cd/A 尖峰效率, cd/A 尖峰功率 效率Im/W 3-1 2300 在20 V 4 5.4 3-2 2700 在27 V 10 3-3 4000 在15 V 10-16 3-4 90 在22 V 4.4 3-5 200 在22 V 1.1 3-6 2500 在21 V 8.5 3-7 2000 在22 V 13 3-8 290 在16 V 1.8 3-9 7000 在15 V 30 15 3-10 1000 在25 V 14 3-11 6500 在15 V 26 3-12 1200 在20 V 9.5 -36- 744 86544 200403229
表3 裝置之電發冷光性 樣品 尖辛輻射 cd/m2 在尖峰輻射下 之效率cd/A 尖峰效率, cd/A 尖峰功率 效率Im/W 3-13 300 在19 V 2.6 3-14 220 在26 V 2.6 3-15 180 在25 V 8.5 3-16 1600 在22 V 11 3-17 100 在22 V 1.2 3-18 4200-5800 在15 V 16-20 3-19 4000-5000 在15 V 17-20 3-20 4800-5400 在17V 15-17 3-21 2300 在20 V 10.5 3-22 4000 在17 V 15-19 在13V 3-23 5000 在17 V 17-22 在13V 3-24 5600 在17 V 22 在14V 86544 -37- 200403229
表3 裝置之電發冷光性 樣品 尖峰輻射 cd/m2 在尖峰輻射下 之效率cd/A 尖峰效率, cd/A 尖峰功率 效率Im/W 3-25 1400 在17 V 5.5 在13V 3-26 8000 在14V 20 在11V 3-27 7000 在17 V 16 在14V 3-28 6000 在15V 15-20 在 14-11V 3-29 6500 在16 V 18 在13V 3-30 6500 在15 V 19 在11V 3-31 6000 在16V 14 在12V 【圖式之簡單說明】 圖1顯示本發明之電荷傳送組合物之式I。 圖2顯示本發明之電荷傳送組合物之式II。 圖3顯示本發明之電荷傳送組合物之式III。 圖4A至4AG顯示本發明之電荷傳送組合物之式1(a)至 I(ag) 〇 圖5顯示多配位體連接基團之式IV(a)至IV(h)。 圖6 A至6M顯示本發明之電荷傳送組合物之式11(a)至 86544 -38- 200403229 II(m)。 圖7A至7E顯示電發冷光銥錯合物之式V(a)至V(e)。 圖8為發光二極體(LED)之概略圖表。 圖9為LED之試驗裝置之概略圖表。 【圖式代表符號說明】 100 裝置 110 陽極層 160 陰極層 120 孔傳送物質之層 140 電子傳送及/或抗猝減物質之層 130 感光層 220 OLED 樣品 210 Minolta LS-110發冷光量尺 250 光譜儀 240 電子遮光器 230 透鏡 260 二極體列陣檢測器 270 電腦 86544 -39-
Claims (1)
- 200403229 拾、申請專利範園: 1· 一種組合物,包含具有式I之喹吟啉衍生物I ) 其中: r1及R2在每次出現可為相同或不同並選自Η、ρ、α、Βι , 垸基、雜燒基、烯基、块基、芳基、雜芳基、伸燒基^芳 _ 基、晞基芳基、块基芳基、伸烷基雜芳基、烯基雜芳基、 炔基滹万基、CnHaFb、〇CnHaFb、c6HcFd& 〇C6HcFd,戈 ^ R2二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 2. ζ為0或1至4之整數。 如申凊專利範圍第1項之組合物,其中 R及R2在每次出現可為相同或不同並選自H、F、Cl、Br、 垸基、雜燒基、芳基、雜芳基、伸垸基芳基、婦基芳基、 块基芳基、伸垸基雜芳基、晞基雜芳基、块基雜芳基、 CnHaFb、OCnHaFb、及叱6邮,或r2二者一起可 構成伸芳基或雜伸芳基,及 η為1至12之整數。 3. 如申請專利範圍第1項之組人 ^ , 1 、、且口物,其中R1選自苯基缔基 經取代苯基烯基、苯基缺_其$ 不丞炔基及經取代苯基炔基。 ?4| 86544 200403229 4. 如申請專利範圍第1項之組合物,其中Ri選自醋酸烷酯及 芳基羰基。 5. 如申請專利範圍第1項之組合物,其中R1選自具有1至12 個竣原子之垸基。 6·如申請專利範圍第1項之組合物,其中R2選自苯基、經取 代苯基、峨淀基及經取代ρ比症基。 7·如申請專利範圍第1項之組合物,其中R2二者可一起選自 二伸芳基及經取代二伸芳基。 8 ·如申請專利範圍第7項之組合物,其中R2 一起選自_伸苯 基、經取代一伸冬基、一伸峨淀基及經取代二伸咐淀基。 9·如申請專利範圍第1項之組合物,其中喹噚啉衍生物係選 自式I⑷至I⑴及I(k)至I(ag) ?4§ 86544Kb) 2- 200403229 h7c1(c)1(d)He)1(f) i(Q) 86544 20040322986544 -4- 200403229I(P)86544 20040322986544 6- 2004032297 si 86544 200403229I (ασI ( ob Br 7 ς g 86544 200403229I (ad )I(〇e) 7 s-6 86544 200403229Kaf ) I(ag). 10.如申請專利範圍第1項之組合物,其中p奎崎p林衍生物為式 I(j)86544 -10- ZUU4U3229 U· —種具有式Π之組合物R及R在每次出現可為相同或不同並選自…卜。,、 燒基:雜燒基、稀基、块基、芳基、雜芳基、伸垸基芳 基、烯基方基、炔基芳基、伸烷基雜芳基、烯基雜芳基、 块2基雉方基、CnHaFb、〇CnHaFb、及 oc^eh,或 R2二者一起可構成伸芳基或雜伸芳基; R在每次出現可為相同或不同並選自單鍵及一基團,其 餘選自伸燒基、雜伸垸基、伸芳基、雜伸芳基、伸芳基 伸燒基、及雜伸芳基伸烷基; Q選自單鍵及多價基; a b、c、及 d為 〇或整數,使 a+b=:2n+i,及c+d=5 m為等於至少2之整數; η為整數; Ρ為0或1 ;及 X為0或1至3之整數。 12·如申請專利範圍第11項之組合物,其中: m為2至1〇之整數; 86544 -11 - 200403229 η為1至12之整數; 但其限制條件為,當Q為單鍵時,ρ為0。 13. 如申請專利範園第u項之組合物,其中·· R1及R2在每次出現可為相同或不同並選自h、f、c卜阶、 垸基、雜燒基、芳基、雜芳基、伸燒基芳基、缔基芳基、 块基万基、伸&基雜芳基、晞基雜芳基、块基雜芳基、 CnHaFb、QCnHaFb、㈣匕及,或r2:者一起可 構成伸芳基或雜伸芳基; m為2至1 〇之整數; η為1至12之整數;及 ρ為0。 14. 如申請專利範圍第u項之组合物,其中⑽選自具有至少 一個接附點《烴基,選自脂肪族基、雜脂肪族基、芳香 放基、及雜芳香族基。 15. 如申請專利範圍第14項之組合物,其中Q係選自伸烷基、 雜伸燒基、伸晞基、雜伸埽基、伸块基及雜伸块基。 16. 如申凊專利範圍第11項之組合物,其中Q係選自單環芳香 族基、多環芳香族基、熔合環芳香族基、單環雜芳香族 基、多環芳香族基、熔合環雜芳香族基、芳基胺、矽烷 及石夕氧燒。 17·如申凊專利範圍第11項之組合物,其中Q係選自式IV(a) 至 IV(h) 86544 -12- 200403229CIV(O)IV(b)IV(c)IV(d )IV(f ) 86544 -13- 200403229Si—( IV(g) /1 — Sic/l in Si I 1 ,Si--0 〕—- •ς; IV(h). 18_如申請專利範圍第11項之組合物,其中R1選自苯基及經取 代苯基。 19·如申請專利範圍第18項之組合物,其中R1係選自經取代苯 基’其具有至少一個取代基,選自F、CH、Br、燒基、雜 烷基、烯基及块基。 2〇·如申請專利範圍第11項之組合物,其中R1係選自酷酸燒酉旨 及芳基羰基。 21·如申請專利範圍第11項之組合物,其中R1係選自具有1至 12個碳原子之燒基。 22.如申請專利範圍第11項之組合物,其中R2係選自苯基、經 取代苯基、吨咬基及經取代p比淀基。 23·如申請專利範圍第11項之組合物,其中r2可一起選自二伸 芳基。 24·如申請專利範圍第23項之組合物,其中二伸芳基係選自 86544 -14- 200403229 二伸苯基、經取代二伸苯基、二伸吡啶基及經取代二伸 口比淀基。 25. 如申請專利範圍第11項之組合物,其中r3係選自芳基、雜 芳基、烷基及雜烷基。 26. 如申請專利範圍第11項之組合物,其中R3係選自苯基及經 取代苯基。 27·如申請專利範圍第11項之組合物,其中R3係選自具有1至 12個碳原子之垸基及雜垸基。 28.如申請專利範圍第丨丨項之組合物,其係選自式π⑻至^⑷ 及II⑴至II(k)86544-15- 200403229-16- 20040322986544 -17- 200403229IKk). 29.如申請專利範圍第11項之組合物,其係選自式11(a)、 11(h)、11(1)及 II(m)-18- 86544 200403229 PH PHIK I )30. —種具有式III之組合物(III) 其中: R1及R2在每次出現可為相同或不同並選自H、F、C卜Br、 烷基、雜烷基、烯基、炔基、芳基、雜芳基、伸烷基芳 基、烯基芳基、块基芳基、伸烷基雜芳基、烯基雜芳基、 炔基雜芳基、CnHaFb、OCnHaFb、C6HcFd及 OC6HcFd,或 R2二者一起可構成伸芳基或雜伸芳基; 86544 -19- 早鍵及一基團,其 雖伸芳基、伸芳基 R3在每次出現可為相同或不同並選自單 係選自伸烷基、雜伸烷基、伸芳基、雜 伸燒基、及雜伸芳基伸烷基; Q選自單鍵及多價基; a b、c、及 d 為 〇 或整數,使 a+b=2n+l,及 c+d=5 ; m為等於至少2之整數; η為2之整數; Ρ為0或1 ;及 X為0或1至4之整數。 31·如申叫專利範圍第π項之組合物,其中q係選自具有至少 二個接附點之烴基,其係選自脂肪族基、雜脂肪族基、 芳香族基、及雜芳香族基。 32·如申請專利範圍第31項之組合物,其中Q係選自伸烷基、 雜伸烷基、伸烯基、雜伸烯基、伸炔基及雜伸炔基。 33·如申請專利範圍第3〇項之組合物,其中q係選自單環芳香 族基、多環芳香族基、熔合環芳香族基、單環雜芳香族 基、多環芳香族基、熔合環芳香族基、芳基胺、矽烷及 碎氧燒。34·如申請專利範圍第3〇項之組合物,其中q係選自式v(a)至 V(e) 86544 -20- 200403229V(d) 86544 -21 Λ 200403229V( e) 35·如申請專利範圍第3〇項之組合物,其中r1係選自苯基晞 基、經取代苯基烯基、苯基炔基及經取代苯基炔基。 36·如申請專利範圍第30項之組合物,其中R1係選自醋酸烷酯 及芳基羰基。 37·如申請專利範圍第3〇項之組合物,其中R1係選自具有1至 12個碳原子之燒基。 38·如申請專利範圍第30項之組合物,其中R2係為η。 39·如申請專利範圍第30項之組合物,其中R3係選自芳基、雜 芳基、燒基及雜燒基。 40·如申請專利範圍第30項之組合物,其中R3係選自苯基及經 取代苯基。 41.如申請專利範圍第30項之組合物,其中R3係選自具有1至 12個碳原子之烷基及雜烷基。 42· —種包含感光層及第二層之電子裝置,其中至少一層包 含具有式I之喹噚琳衍生物86544 -22- R及R在每次出現可為相同或不同並選自H、f、c卜Br、 烷基、雜烷基、烯基、炔基、芳基、雜芳基、伸烷基芳〜 基、稀基芳基、炔基芳基、伸燒基雜芳基、烯基雜芳基、 炔基雜芳基、CnHJb、OCnHaFb、C6HcFd 及 〇C6HeFd,或 R2二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;及 ζ為0或1至4之整數。 43·如申請專利範園第42項之裝置,其中第二層包含具有圖1 所示之式I之ρ奎巧琳衍生物,此處,其中: R1及R2在每次出現可為相同或不同並選自H、F、ci、Bi·、 燒基、雜烷基、芳基、雜芳基、伸燒基芳基、埽基芳基、 块基芳基、伸烷基雜芳基、晞基雜芳基、炔基雜芳基、 CnHaFb、〇CnHaFb、C6HcFd 及 OC6HcFd,或 R2二者一起可 構成伸芳基或雜伸芳基,及 η為1至12之整數。 44·如申請專利範圍第42項之裝置,其中R1係選自苯基烯基、 經取代苯基烯基、苯基炔基及經取代苯基炔基。 45·如申請專利範圍第42項之裝置,其中R1係選自醋酸烷酯及 方基幾基。 46·如申請專利範圍第42項之裝置,其中R1係選自具有1至12 個碳原子之烷基。 47·如申請專利範圍第42項之裝置,其中R2係選自苯基、經取 86544 -23- 200403229 代苯基、吡啶基及經取代吡啶基。 48·如申请專利範圍第42項之裝置,其中R2二去i —可』一起選自 二伸芳基及經取代二伸芳基。 49·如申請專利範圍第42項之裝置,其中R2—起選自二伸苯 基、經取代二伸苯基、二伸吡啶基及經取代二伸吡啶基。 50.如申請專利範圍第42項之裝置,其中喹呤啉衍生物係選 自式 1(a)至 I(i)及 I(k)至 I(ag)1(〇) 1(b)1(c) 86544 -24- 2004032291(d)1(f)1(g) 86544 -25- 20040322920040322986544 -27- 20040322986544 -28- 20040322986544 -29 200403229I (αα ) BrI ( ab ) Brl(ac) 86544 -30- 2004032290I (ad )I(〇e) I (af ) 77x 86544 -31 - 200403229I(ag )# 51.如申請專利範圍第42項之裝置,其中喹噚啉衍生物具有 式 I(j) ηKi ), 52. —種包含感光層及第二層之電子裝置,其中至少一層包 含選自式II及式III之喹呤啉衍生物86544 -32- 200403229其中: R及R在每次出現可為相同或不同並選自H、f、c卜Br、 烷基、雜烷基、蹄基、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、OCnHaFb、C6HeFd 及 〇C6HeFd,或 R二者一起可構成伸芳基或雜伸芳基; R在每次出現可為相同或不同並選自單键及一基團,其 係選自伸烷基、雜伸烷基、伸芳基、雜伸芳基、伸芳基 伸燒基、及雜伸芳基伸烷基; Q選自單鍵及多價基; a b、C、及d為 〇或整數,使a+b=2n+1,及c+d=5 ; m為等於至少2之整數; η為整數; Ρ為0或1 ;及 χ為0或1至3之整數。 53. 如申請專利範圍第52項之裝置,其中第二層包含具有式η 之峻3 Ρ林衍生物 86544 200403229且其中: m為2至10之整數; η為1至12之整數; 但其限制條件為,當Q為單鍵時,ρ為0。 54.如申請專利範圍第52項之裝置,其中第二層包含具有式II 之峻$淋衍生物(II) 且其中: R1及R2在每次出現可為相同或不同並選自H^F'ChBr、 烷基、雜烷基、芳基、雜芳基、伸烷基芳基、烯基芳基、 決基芳基、伸院基雜芳基、晞基雜芳基、块基雜芳基、 CnHaFb、OCnHaFb、C6HcFd及 OC6HcFd,或 R2二者一起可 構成伸芳基或雜伸芳基; 86544 -34- 200403229 m為2至10之整數; η為1至12之整數;及 ρ為0。 55·如申請專利範圍第52項之裝置,其中q係選自具有至少二 個接附點之烴基,選自脂肪族基、雜脂肪族基、芳香族 基、及雜芳香族基。 56. 如申請專利範圍第52項之裝置,其中Q係選自伸烷基、雜 伸烷基、伸烯基、雜伸烯基、伸炔基及雜伸炔基。 57. 如申請專利範圍第52項之裝置,其中Q係選自單環芳夭族 基、多環芳香族基、熔合環芳香族基、單環雜芳 多環芳香族基、熔合環芳香族基、芳基胺、矽烷及碎"氧 58. 如申請專利範圍第52項之裝置,其中 丁 V你選自式v(a) V(e) W-35- V(Q) 12 86544 200403229V(b) mϊί:; 86544 -36- 20040322959.如申請專利範圍第52項之裝置,其中喹噚啉衍生物係選 , 自式 11(b)至 11(g)及 II(i)至 II(k) φ11(b) ?84 8654411(d) -37- 20040322986544 -38- 200403229IKK). 86544 -39- 200403229 60·如申請專利範圍第52項之裝置,其中喹噚啉衍生物係選 自式 11(a)、11(h)、11(1)及 II(m)86544-40- 20040322961.如申請專利範圍第41-59項之電子裝置,其中該裝置為發 光二極體、發光電化學電池或光檢測器。 86544 -41 -
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2003
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- 2003-07-02 US US10/612,237 patent/US7074534B2/en not_active Expired - Fee Related
- 2003-07-02 US US10/612,482 patent/US7265378B2/en not_active Expired - Lifetime
- 2003-07-02 US US10/612,493 patent/US6962995B2/en not_active Expired - Lifetime
- 2003-07-09 EP EP03763462A patent/EP1520452A2/en not_active Withdrawn
- 2003-07-09 WO PCT/US2003/021612 patent/WO2004005406A2/en not_active Application Discontinuation
- 2003-07-09 EP EP03763463A patent/EP1520305A2/en not_active Withdrawn
- 2003-07-09 CA CA002492688A patent/CA2492688A1/en not_active Abandoned
- 2003-07-09 JP JP2004520121A patent/JP2005533341A/ja active Pending
- 2003-07-09 JP JP2004520122A patent/JP2005533139A/ja active Pending
- 2003-07-09 JP JP2004520120A patent/JP2006505115A/ja active Pending
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- 2003-07-09 WO PCT/US2003/021613 patent/WO2004006354A2/en not_active Application Discontinuation
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- 2003-07-09 KR KR1020117007652A patent/KR20110043792A/ko not_active Application Discontinuation
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- 2003-07-09 WO PCT/US2003/021617 patent/WO2004006352A2/en not_active Application Discontinuation
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- 2003-07-09 KR KR1020057000318A patent/KR101011883B1/ko not_active IP Right Cessation
- 2003-07-09 CA CA002492690A patent/CA2492690A1/en not_active Abandoned
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- 2003-07-09 EP EP03763460A patent/EP1520308A2/en not_active Withdrawn
- 2003-07-09 WO PCT/US2003/021618 patent/WO2004006355A2/en not_active Application Discontinuation
- 2003-07-09 AU AU2003249016A patent/AU2003249016A1/en not_active Abandoned
- 2003-07-09 CN CNA038164620A patent/CN1668616A/zh active Pending
- 2003-07-09 AU AU2003251850A patent/AU2003251850A1/en not_active Abandoned
- 2003-07-09 KR KR1020107021786A patent/KR20100110401A/ko not_active Application Discontinuation
- 2003-07-10 TW TW092118919A patent/TW200413365A/zh unknown
- 2003-07-10 TW TW092118886A patent/TW200403229A/zh unknown
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- 2003-07-10 TW TW092118922A patent/TWI330645B/zh not_active IP Right Cessation
- 2003-07-10 TW TW092118918A patent/TW200415225A/zh unknown
- 2003-12-08 US US10/612,704 patent/US7399432B2/en not_active Expired - Fee Related
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2005
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2006
- 2006-04-21 HK HK06104776.6A patent/HK1084775A1/xx not_active IP Right Cessation
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2007
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- 2008-05-23 US US12/126,061 patent/US7914706B2/en active Active
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2009
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI665287B (zh) * | 2018-08-23 | 2019-07-11 | 祥德科技股份有限公司 | Quinoxaline dimer-containing electron transport material as organic light-emitting element |
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