CN100428522C - 硼和铝化合物在电子组件中的应用 - Google Patents
硼和铝化合物在电子组件中的应用 Download PDFInfo
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- CN100428522C CN100428522C CNB018212573A CN01821257A CN100428522C CN 100428522 C CN100428522 C CN 100428522C CN B018212573 A CNB018212573 A CN B018212573A CN 01821257 A CN01821257 A CN 01821257A CN 100428522 C CN100428522 C CN 100428522C
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- aryl
- compound
- carbon atom
- boron
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- 229910052796 boron Inorganic materials 0.000 title claims abstract description 31
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 150000001399 aluminium compounds Chemical class 0.000 title claims abstract description 22
- 229940077746 antacid containing aluminium compound Drugs 0.000 title abstract 2
- 239000000463 material Substances 0.000 claims abstract description 26
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- -1 4-pyridine radicals Chemical class 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 6
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 239000004411 aluminium Substances 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 230000000903 blocking effect Effects 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 claims description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- NGDCLPXRKSWRPY-UHFFFAOYSA-N Triptycene Chemical compound C12=CC=CC=C2C2C3=CC=CC=C3C1C1=CC=CC=C12 NGDCLPXRKSWRPY-UHFFFAOYSA-N 0.000 claims description 3
- 230000021615 conjugation Effects 0.000 claims description 3
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 2
- SXWIAEOZZQADEY-UHFFFAOYSA-N 1,3,5-triphenylbenzene Chemical compound C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)=C1 SXWIAEOZZQADEY-UHFFFAOYSA-N 0.000 claims description 2
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 claims description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 2
- 150000002475 indoles Chemical class 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims description 2
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 2
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 2
- 150000003233 pyrroles Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 37
- 239000000243 solution Substances 0.000 description 26
- 238000003756 stirring Methods 0.000 description 23
- 239000010410 layer Substances 0.000 description 22
- 238000004128 high performance liquid chromatography Methods 0.000 description 21
- 208000035126 Facies Diseases 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 229910000085 borane Inorganic materials 0.000 description 10
- 239000000376 reactant Substances 0.000 description 10
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- 230000008901 benefit Effects 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 125000001153 fluoro group Chemical group F* 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 230000009102 absorption Effects 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 125000000707 boryl group Chemical group B* 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 229920000767 polyaniline Polymers 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000002322 conducting polymer Substances 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
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- 230000005525 hole transport Effects 0.000 description 2
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- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Inorganic materials [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 229910001092 metal group alloy Inorganic materials 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000005259 triarylamine group Chemical group 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 150000000182 1,3,5-triazines Chemical class 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- CDKCEZNPAYWORX-UHFFFAOYSA-N 1-tert-butyl-4-(4-tert-butylphenyl)benzene Chemical group C1=CC(C(C)(C)C)=CC=C1C1=CC=C(C(C)(C)C)C=C1 CDKCEZNPAYWORX-UHFFFAOYSA-N 0.000 description 1
- OHZMNOWLGDVPNW-UHFFFAOYSA-N 1-tert-butyl-4-(4-tert-butylphenyl)benzene;lithium Chemical compound [Li].C1=CC(C(C)(C)C)=CC=C1C1=CC=C(C(C)(C)C)C=C1 OHZMNOWLGDVPNW-UHFFFAOYSA-N 0.000 description 1
- OOLUVSIJOMLOCB-UHFFFAOYSA-N 1633-22-3 Chemical compound C1CC(C=C2)=CC=C2CCC2=CC=C1C=C2 OOLUVSIJOMLOCB-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- AQLLMLUUWKQYRG-UHFFFAOYSA-N [B++] Chemical compound [B++] AQLLMLUUWKQYRG-UHFFFAOYSA-N 0.000 description 1
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
- 239000011469 building brick Substances 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
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- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- BVBRZOLXXOIMQG-UHFFFAOYSA-N fluoroborane Chemical compound FB BVBRZOLXXOIMQG-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
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- 229910000765 intermetallic Inorganic materials 0.000 description 1
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- 239000013580 millipore water Substances 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
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- 229920003227 poly(N-vinyl carbazole) Chemical class 0.000 description 1
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- 238000004321 preservation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical group C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
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Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00128296.1 | 2000-12-22 | ||
| EP00128296A EP1217668A1 (de) | 2000-12-22 | 2000-12-22 | Verwendung von Bor- und Aluminium-Verbindungen in Elektronik-Bauteilen |
Publications (2)
| Publication Number | Publication Date |
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| CN1554127A CN1554127A (zh) | 2004-12-08 |
| CN100428522C true CN100428522C (zh) | 2008-10-22 |
Family
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| Application Number | Title | Priority Date | Filing Date |
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| CNB018212573A Expired - Fee Related CN100428522C (zh) | 2000-12-22 | 2001-12-20 | 硼和铝化合物在电子组件中的应用 |
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Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1217668A1 (de) * | 2000-12-22 | 2002-06-26 | Covion Organic Semiconductors GmbH | Verwendung von Bor- und Aluminium-Verbindungen in Elektronik-Bauteilen |
| JP4804662B2 (ja) * | 2001-07-11 | 2011-11-02 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子及び表示装置 |
| JP4374842B2 (ja) * | 2001-11-09 | 2009-12-02 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子及び表示装置 |
| JP4300788B2 (ja) * | 2001-12-06 | 2009-07-22 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子および表示装置 |
| WO2004056839A1 (ja) * | 2002-12-19 | 2004-07-08 | Semiconductor Energy Laboratory Co., Ltd. | 有機金属錯体および前記有機金属錯体を用いた電界発光素子、並びに前記電界発光素子を用いた発光装置 |
| US6902833B2 (en) | 2003-04-01 | 2005-06-07 | University Of Southern California | Materials and structures for enhancing the performance or organic light emitting devices |
| US20040209116A1 (en) * | 2003-04-21 | 2004-10-21 | Xiaofan Ren | Organic light emitting devices with wide gap host materials |
| US7018723B2 (en) * | 2003-07-25 | 2006-03-28 | The University Of Southern California | Materials and structures for enhancing the performance of organic light emitting devices |
| US7795801B2 (en) * | 2003-09-30 | 2010-09-14 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, illuminator, display and compound |
| JP4243237B2 (ja) * | 2003-11-10 | 2009-03-25 | 淳二 城戸 | 有機素子、有機ｅｌ素子、有機太陽電池、及び、有機ｆｅｔ構造、並びに、有機素子の製造方法 |
| US7074502B2 (en) * | 2003-12-05 | 2006-07-11 | Eastman Kodak Company | Organic element for electroluminescent devices |
| TW200528536A (en) * | 2003-12-19 | 2005-09-01 | Showa Denko Kk | Boron-containing polymer compound and organic light emitting device using the same |
| JP4600288B2 (ja) * | 2003-12-24 | 2010-12-15 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置および表示装置 |
| JP4600287B2 (ja) * | 2003-12-24 | 2010-12-15 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置および表示装置 |
| DE10361385B4 (de) * | 2003-12-29 | 2011-07-28 | OSRAM Opto Semiconductors GmbH, 93055 | Polymere, phosphoreszierende, organisch halbleitende Emittermaterialien auf Basis perarylierter Borane, Verfahren zu deren Herstellung und Verwendungen davon |
| US8178214B2 (en) * | 2004-02-26 | 2012-05-15 | Konica Minolta Holdings, Inc. | Material for organic electroluminescence element, organic electroluminescence element, display device and illumination device |
| US7790890B2 (en) * | 2004-03-31 | 2010-09-07 | Konica Minolta Holdings, Inc. | Organic electroluminescence element material, organic electroluminescence element, display device and illumination device |
| DE102004023219B4 (de) * | 2004-05-11 | 2006-03-09 | Siemens Ag | Organisches elektronisches Bauelement |
| JP5242380B2 (ja) | 2005-05-03 | 2013-07-24 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子 |
| JP5040080B2 (ja) * | 2005-07-20 | 2012-10-03 | Ｊｎｃ株式会社 | 有機電界発光素子 |
| DE102006025846A1 (de) * | 2006-06-02 | 2007-12-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
| JP5326280B2 (ja) * | 2006-06-15 | 2013-10-30 | 東レ株式会社 | 発光素子材料および発光素子 |
| GB0625789D0 (en) * | 2006-12-22 | 2007-02-07 | Univ Cardiff | Organometallic sensor device |
| JP4798128B2 (ja) * | 2007-12-21 | 2011-10-19 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子及び表示装置 |
| CN101633668B (zh) * | 2008-07-24 | 2015-06-03 | 通用电气公司 | 含苯吡啶单元的化合物 |
| JP5968885B2 (ja) | 2010-07-30 | 2016-08-10 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネセンスデバイス |
| JP5379179B2 (ja) * | 2011-03-17 | 2013-12-25 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子及び表示装置 |
| JP5129359B2 (ja) * | 2011-03-17 | 2013-01-30 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子及び表示装置 |
| JP5767915B2 (ja) * | 2011-09-06 | 2015-08-26 | 株式会社日本触媒 | ホウ素含有化合物 |
| TWI425076B (zh) | 2011-11-01 | 2014-02-01 | Ind Tech Res Inst | 咔唑衍生物及包含此衍生物之有機發光二極體 |
| CN103183691B (zh) * | 2011-12-29 | 2016-05-25 | 昆山维信诺显示技术有限公司 | 含有取代或非取代咔唑基的6-均三甲苯基-6H-6-硼杂苯并[cd]芘衍生物及制备方法及应用及含其的发光器件 |
| CN102899027B (zh) * | 2012-04-12 | 2014-03-12 | 杭州师范大学 | 一类含硼发光材料及其制备方法与应用 |
| CN102827196B (zh) * | 2012-09-12 | 2015-06-03 | 山西大学 | 一种含硼吲哚[3,2-b]咔唑衍生物及其制备方法和应用 |
| TWI599570B (zh) * | 2012-09-28 | 2017-09-21 | 新日鐵住金化學股份有限公司 | Compounds for organic electroluminescent devices and organic electroluminescent devices |
| CN103360416B (zh) * | 2013-07-16 | 2016-03-30 | 山西大学 | 一种基于咔唑的芳基硼化合物及其制备和应用 |
| CN103483365B (zh) * | 2013-09-03 | 2016-04-27 | 太仓碧奇新材料研发有限公司 | 一种并三噻吩硼烷晶体管材料及其制备方法 |
| CN103483364A (zh) * | 2013-09-03 | 2014-01-01 | 太仓碧奇新材料研发有限公司 | 一种双苯并噻吩硼烷发光材料及其制备方法 |
| CN103450240B (zh) * | 2013-09-03 | 2016-04-27 | 太仓碧奇新材料研发有限公司 | 一种芘基硼烷分子电子材料及其制备方法 |
| EP3904361A3 (de) | 2013-10-02 | 2022-04-20 | Merck Patent GmbH | Borenthaltende verbindungen |
| CN103601747B (zh) * | 2013-11-27 | 2015-09-30 | 山西大学 | 一种基于吲哚[3,2-b]咔唑的芳基硼化合物及其制备和应用 |
| KR102313358B1 (ko) * | 2014-07-10 | 2021-10-18 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| CN109804027B (zh) | 2016-11-25 | 2022-03-01 | 株式会社Lg化学 | 离子化合物、包含其的涂覆组合物和有机发光二极管 |
| TWI636033B (zh) * | 2017-09-11 | 2018-09-21 | 晶宜科技股份有限公司 | 有機電激發光裝置及其材料 |
| CN109734739B (zh) * | 2019-02-25 | 2021-06-25 | 南京邮电大学 | 一种有机硼发光材料及其制备方法和应用 |
| CN113501834A (zh) * | 2021-06-21 | 2021-10-15 | 兰州大学 | 一种激发可调的单组分有机三芳基硼室温磷光材料 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000290373A (ja) * | 1999-04-08 | 2000-10-17 | Dainippon Ink & Chem Inc | 吸水性複合体の製造方法 |
| JP2000290645A (ja) * | 1999-04-12 | 2000-10-17 | Toyo Ink Mfg Co Ltd | 有機エレクトロルミネッセンス素子用材料およびそれを使用した有機エレクトロルミネッセンス素子 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW466256B (en) * | 1995-11-24 | 2001-12-01 | Ciba Sc Holding Ag | Borate photoinitiator compounds and compositions comprising the same |
| US6312835B1 (en) * | 1997-02-13 | 2001-11-06 | Queen's University At Kingston | Luminescent compounds and methods of making and using same |
| JPH10321374A (ja) * | 1997-05-20 | 1998-12-04 | Tdk Corp | 有機ｅｌ素子 |
| DE19803889A1 (de) * | 1998-01-31 | 1999-08-05 | Bosch Gmbh Robert | Elektrolumineszierende Anordnung unter Verwendung von dotierten Blendsystemen |
| DE19829947A1 (de) | 1998-07-04 | 2000-01-05 | Bayer Ag | Elektrolumineszierende Anordnungen mit Bor-Chelaten |
| DE69932263T2 (de) | 1999-01-08 | 2007-06-06 | Chisso Corp. | Borderivate und organische elektrolumineszierende verbindungen |
| US6391482B1 (en) * | 1999-02-04 | 2002-05-21 | Matsushita Electric Industrial Co., Ltd. | Organic material for electroluminescent device and electroluminescent device using the same |
| DE50104149D1 (de) * | 2000-12-22 | 2004-11-18 | Covion Organic Semiconductors | Bor- oder aluminium-spiroverbindungen, deren verwendung in elekronikindustrie |
| EP1217668A1 (de) * | 2000-12-22 | 2002-06-26 | Covion Organic Semiconductors GmbH | Verwendung von Bor- und Aluminium-Verbindungen in Elektronik-Bauteilen |
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2000
- 2000-12-22 EP EP00128296A patent/EP1217668A1/de not_active Withdrawn
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2001
- 2001-12-20 JP JP2002553254A patent/JP2005501372A/ja active Pending
- 2001-12-20 CN CNB018212573A patent/CN100428522C/zh not_active Expired - Fee Related
- 2001-12-20 KR KR1020037008201A patent/KR100832765B1/ko active IP Right Grant
- 2001-12-20 EP EP01984879A patent/EP1346421A1/de not_active Withdrawn
- 2001-12-20 US US10/250,594 patent/US7060369B2/en not_active Expired - Fee Related
- 2001-12-20 WO PCT/EP2001/015176 patent/WO2002052661A1/de active Application Filing
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- 2006-05-18 US US11/436,854 patent/US7279603B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000290373A (ja) * | 1999-04-08 | 2000-10-17 | Dainippon Ink & Chem Inc | 吸水性複合体の製造方法 |
| JP2000290645A (ja) * | 1999-04-12 | 2000-10-17 | Toyo Ink Mfg Co Ltd | 有機エレクトロルミネッセンス素子用材料およびそれを使用した有機エレクトロルミネッセンス素子 |
Also Published As
| Publication number | Publication date |
|---|---|
| US7279603B2 (en) | 2007-10-09 |
| CN1554127A (zh) | 2004-12-08 |
| KR100832765B1 (ko) | 2008-05-27 |
| EP1217668A1 (de) | 2002-06-26 |
| US20060241321A1 (en) | 2006-10-26 |
| JP2005501372A (ja) | 2005-01-13 |
| US20040058194A1 (en) | 2004-03-25 |
| WO2002052661A1 (de) | 2002-07-04 |
| EP1346421A1 (de) | 2003-09-24 |
| US7060369B2 (en) | 2006-06-13 |
| KR20030077556A (ko) | 2003-10-01 |
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