WO2002052661A1 - Verwendung von bor- und aluminium-verbindungen in elektronik-bauteilen - Google Patents
Verwendung von bor- und aluminium-verbindungen in elektronik-bauteilenInfo
- Publication number
- WO2002052661A1 WO2002052661A1 PCT/EP2001/015176 EP0115176W WO02052661A1 WO 2002052661 A1 WO2002052661 A1 WO 2002052661A1 EP 0115176 W EP0115176 W EP 0115176W WO 02052661 A1 WO02052661 A1 WO 02052661A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- same
- different
- atoms
- boron
- compounds
- Prior art date
Links
- 229910052796 boron Inorganic materials 0.000 title claims abstract description 30
- 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 abstract 2
- 229940077746 antacid containing aluminium compound Drugs 0.000 title abstract 2
- 239000000463 material Substances 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 28
- -1 9-anthracenyl Chemical group 0.000 claims description 21
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims description 6
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 6
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-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
- 150000001338 aliphatic hydrocarbons Chemical class 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 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
- 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 3
- 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 3
- OOLUVSIJOMLOCB-UHFFFAOYSA-N 1633-22-3 Chemical compound C1CC(C=C2)=CC=C2CCC2=CC=C1C=C2 OOLUVSIJOMLOCB-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 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
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-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
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=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
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- MWVTWFVJZLCBMC-UHFFFAOYSA-N 4,4'-bipyridine Chemical group C1=NC=CC(C=2C=CN=CC=2)=C1 MWVTWFVJZLCBMC-UHFFFAOYSA-N 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl 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
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 150000001638 boron Chemical class 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004986 diarylamino group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 125000005000 thioaryl group Chemical group 0.000 claims description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 26
- 239000010410 layer Substances 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 238000004128 high performance liquid chromatography Methods 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 20
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 230000008901 benefit Effects 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000002274 desiccant Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- WZWGERGANZMXOM-UHFFFAOYSA-N fluoro-bis(2,4,6-trimethylphenyl)borane Chemical compound CC1=CC(C)=CC(C)=C1B(F)C1=C(C)C=C(C)C=C1C WZWGERGANZMXOM-UHFFFAOYSA-N 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 229920000767 polyaniline Polymers 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-UHFFFAOYSA-N 0.000 description 2
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 2
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 2
- FEYDZHNIIMENOB-UHFFFAOYSA-N 2,6-dibromopyridine Chemical compound BrC1=CC=CC(Br)=N1 FEYDZHNIIMENOB-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- NVILQTPPWMJNGF-UHFFFAOYSA-N [3,5-bis(trimethylstannyl)phenyl]-trimethylstannane Chemical compound C[Sn](C)(C)C1=CC([Sn](C)(C)C)=CC([Sn](C)(C)C)=C1 NVILQTPPWMJNGF-UHFFFAOYSA-N 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 229910000085 borane Inorganic materials 0.000 description 2
- 229920001940 conductive polymer Chemical class 0.000 description 2
- FAMGJMYDHOESPR-UHFFFAOYSA-M dilithium;carbanide;bromide Chemical compound [Li+].[Li+].[CH3-].[Br-] FAMGJMYDHOESPR-UHFFFAOYSA-M 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
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- 125000005259 triarylamine group Chemical group 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 150000000182 1,3,5-triazines Chemical class 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical class N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- IERDDDBDINUYCD-UHFFFAOYSA-N 1-[4-[4-(9h-carbazol-1-yl)phenyl]phenyl]-9h-carbazole Chemical group C12=CC=CC=C2NC2=C1C=CC=C2C(C=C1)=CC=C1C(C=C1)=CC=C1C1=C2NC3=CC=CC=C3C2=CC=C1 IERDDDBDINUYCD-UHFFFAOYSA-N 0.000 description 1
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- OHZMNOWLGDVPNW-UHFFFAOYSA-N 1-tert-butyl-4-(4-tert-butylphenyl)benzene;lithium Chemical group [Li].C1=CC(C(C)(C)C)=CC=C1C1=CC=C(C(C)(C)C)C=C1 OHZMNOWLGDVPNW-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
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- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
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- BCDSSSXUYLVMQY-UHFFFAOYSA-N bis(2,4,6-trimethylphenyl)boron Chemical compound CC1=CC(C)=CC(C)=C1[B]C1=C(C)C=C(C)C=C1C BCDSSSXUYLVMQY-UHFFFAOYSA-N 0.000 description 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 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
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- 238000010438 heat treatment 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
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000013580 millipore water Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- BZBAYMUKLAYQEO-UHFFFAOYSA-N phenylborane Chemical compound BC1=CC=CC=C1 BZBAYMUKLAYQEO-UHFFFAOYSA-N 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000008149 soap solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
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
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/658—Organoboranes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
- H10K85/6565—Oxadiazole compounds
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- 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
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Definitions
- the present invention relates to the use of boron and aluminum compounds in electronics, in particular in phosphorescence OLED devices.
- Base usually triarylamine-based hole transporter
- Electroluminescent devices are Electroluminescent devices.
- Solid-state laser diodes and organic photodetectors prove.
- OLEDs organic light-emitting diodes
- LCD liquid crystal displays
- An organic electroluminescent device usually consists of several layers, which are preferably applied to one another by means of vacuum methods. These layers are one:
- Carrier plate substrate (usually glass or plastic films).
- Transparent anode usually indium tin oxide, ITO.
- Hole Injection Layer e.g. B. based on copper phthalocyanine (CuPc), conductive polymers such as polyaniline (PANI), or polythiophene derivatives (such as PEDOT).
- CuPc copper phthalocyanine
- PANI polyaniline
- PEDOT polythiophene derivatives
- Hole transport layer usually based on triarylamine derivatives.
- Emission layer EML
- EML Electron Transport Layer
- Electron Injection Layer this layer can partially coincide with layer 6 or a small part of the cathode is specially treated or specially deposited.
- Cathode here metals, metal combinations or metal alloys with a low exit function are generally used.
- This entire device is of course structured according to Qe after application), contacted and finally hermetically sealed, since i. d. R. drastically reduces the life of such devices in the presence of water and / or air.
- HBL hole blocking layers
- the individual OLED will emit light that has a color that the EML specifies. In this way it is possible, depending on the EML, to generate the three basic colors (blue, green, red).
- AIQ 3 has long been the best compromise for the various requirements.
- the compound has an obviously usable one
- a major practical disadvantage of AIQ 3 is the strong hygroscopy of it
- AIQ 3 which is synthesized and stored under normal conditions, still contains one in addition to the hydroxyquinoline ligands
- AIQ 3 must therefore be used in OLEDs in complicated, multi-stage,
- AIQ 3 is also used as ETL on the one hand, and on the other hand there is the question of the host material for the actual one
- Triazole derivative The operational lifespans in particular still require a great deal of optimization.
- the compounds are distinguished by the following properties:
- the described boron or aluminum compounds are characterized by a high oxidation stability. When used in corresponding devices according to the invention, this can lead to a significant increase in the operating life. Furthermore, the manufacture of these devices is simplified. 4. The described boron or aluminum compounds have no recognizable
- Hygroscopy as well as high stability against atmospheric oxygen. Storage for several days or weeks with access to air and water vapor does not change the substances. The attachment of water to the compounds cannot be demonstrated. Of course, this has the advantage that the substances can be cleaned, transported, stored and prepared for use under simpler conditions. In contrast to the operations with the AIQ 3 , the use does not have to take place continuously under protective gas.
- the described boron or aluminum compounds can be produced in a reproducible manner with reliable high purity and have no batch fluctuation. An industrial process for producing the electroluminescent devices according to the invention is therefore much more efficient.
- the boron or aluminum compounds described are also characterized by high temperature stability. However, this is not shown as a decisive advantage, it should only be pointed out that this property is also achieved very satisfactorily by the boranes or aluminum organyles.
- the described boron or aluminum compounds have excellent solubility in organic solvents. This means that these materials can also be processed from solution using coating or printing techniques. This property is also advantageous in the usual processing by evaporation, since it considerably simplifies the cleaning of the systems and the shadow masks used.
- Y. Shirota (eg Y. Shirota et al., Adv. Mater. 1999, 11, 283) describes a bisthiophene-bis-borane compound in OLEDs. But here u. a. on an exciplex
- oligoboryl compounds (mainly with anthracene bridges or substituents) are presented, about which - by the same authors - in J. Am. Chem. Soc, 2000, 122, 6335.
- a clear disadvantage of these compounds can also be seen here at once: they have a strong absorption in the range of visible light (cf. the above-mentioned location, FIG. 2).
- Tamano, M. et al. report in JP-2000-290645 and JP-2000-290373 about various borane compounds in OLED applications. However, nothing is mentioned here about a possible use in the above. novel phosphorescence OLEDs are reported.
- the boron or aluminum compounds are generally made using known methods known to those skilled in the art, such as vacuum evaporation, or also from solution by spin coating or using various printing processes (for example ink-jet printing, offset printing, etc.), applied to a substrate in the form of a film.
- the present invention therefore relates to the use of substituted boron or aluminum compounds of the general formula (I)
- Aryl is a carbo- or heterocyclic aromatic ring or
- Ring system with 2 to 60 C atoms, or several aromatic rings, each with 6 to 14 C atoms, which are connected to one another by a conjugated or non-conjugated link or via one or more metal atoms (sandwich complex);
- Ar ,, Ar 2 is phenyl, 1- or 2- at each occurrence
- Q1, Q2, Q3 is the same or different on each occurrence and stands for CN, F, Cl or a straight-chain or branched or cyclic alkyl or alkoxy group with 1 to 20 C atoms, one or more non-adjacent CH 2 groups by -O-, -S-, -CO-, -COO-, -O-CO-, -NR 1 - - (NR 2 R 3 ) + A " ; or -CONR 4 - and where one or several H atoms can be replaced by F, or an aryl or heteroaryl group with 4 to 14 C atoms, which can be substituted by one or more non-aromatic radicals R ' ;
- R ⁇ R 2 , R 3 , R 4 are the same or different, H or an aliphatic or aromatic hydrocarbon radical having 1 to 20 carbon atoms; m the same or different 0, 1, 2, 3, 4, 5; x identical or different 0, 1, 2, 3, 4, 5; y the same or different 0, 1, 2, 3, 4, 5; n 2, 3, 4, 5, 6;
- the boron or aluminum compounds are preferably used in electron transport layers (ETL), hole blocking layers (HBL) or as host systems in the emission layer (EML) in the phosphorescence OLEDs.
- Triplet emitters are suitable as dopants for this.
- they have the advantage that they have a constant brightness even at elevated temperatures (e.g. heating to 130 ° C for several hours).
- the voltage to be applied for a given brightness remains largely constant. It is therefore not necessary to readjust the voltage during continuous operation in order to maintain an initial brightness. This advantage is particularly noticeable in battery operation, since the maximum voltage that is economically possible is severely restricted.
- boron or aluminum compounds in which aryl in formula (I) has the following meaning: benzene, biphenyl, 1, 2- or 1, 3- or 1, 4-terphenyl, tetraphenyl, naphthalene, Fluorene, phenanthrene, 1, 3,5-triphenylbenzene, pyrene, perylene, chrysene, trypticen, [2.2] paracyclophane, ferrocene, pyridine, pyridazine, 4,5-benzopyridazine, pyrimidine .
- boron or aluminum compounds of the formula (I) in which the aryl substituents Ar and Ar 2 are each the same or different and are phenyl, 1-naphthyl, 2-naphthyl.
- R1, R2, R3, R4 is, in each case, the same or different, an alkyl, alkyloxy or aryl radical having 1 to 20 carbon atoms, and corresponding fluoroalkyl or fluoroalkoxy radicals;
- R5, R6 are in each case the same or different H, CN, F, Cl, Br, I, a straight-chain, branched or cyclic alkyl or alkoxy group, a thioalkyl or thioaryl group, a nitro group, a diaryl or dialkylamino group and an ester, amide or carboxylic acid group.
- Q3 in each case the same or different with each occurrence, is CN, F, Cl or a straight-chain or branched or cyclic alkyl or alkoxy group with 1 to 20 C atoms, one or more non-adjacent CH 2 groups being denoted by -O-, -S-, -CO-, -COO-, -O-CO-, -NR 1 -, - (NR 2 R 3 ) + A " , or -CONR 4 - can be replaced and where one or more H atoms can be replaced by F, or an aryl or heteroaryl group with 4 to 14 C atoms, which are characterized by one or more, non-aromatic
- Radicals R ' can be substituted
- R 1 , R 2 , R 3 , R 4 are each the same or different, hydrogen or an aliphatic or aromatic hydrocarbon radical with 1 to
- Aryl in formula (I) or (II) can correspond to one of the substituted benzenes below,
- aryl in formula (I) or (II) can correspond to one of the substituted 1, 3,5-triphenylbenzene, pyrene, perylene, chrysene, trypticen, [2.2] paracyclophane, 1, 1 ' -ferrocene,
- Aryl in formula (I) or (II) can correspond to one of the substituted pyridines, pyridazines, 4,5-benzopyridazines, pyrimidines, pyrazines below,
- 1, 3,5-triazines, 1, 2,5- or 1, 3,4-oxadiazole, or aryl in formula (I) or (II) can be one of the below
- the residues AR, to AR 8 each have the same meaning as the residues Ar, and Ar 2 in formula (I).
- residues AR 1 to AR 8 are particularly preferably the following residues:
- boron or aluminum compounds of the formulas (I) and (II) takes place, for example, by reacting a halogenated aromatic (preferably: bromoaromatic) with a metal (for example Li, Mg), a metal alloy (for example Li-Al-Alloy) or a metal compound (n-, sec-, terf-butyllithium, Grignard-
- a halogenated aromatic preferably: bromoaromatic
- a metal for example Li, Mg
- a metal alloy for example Li-Al- Alloy
- a metal compound n-, sec-, terf-butyllithium, Grignard-
- Diaryl boron or aluminum halides since according to this method - compared to reactions of Grignard compounds with diaryl boron halides already described in the literature [A. Schulz, W. Kaim, Chem. Ber., 1989, 122, 1863-1868] - significantly better yields can be achieved.
- Example 1 Synthesis of 1,4-bis (dimesitylboryl) benzene A well-stirred solution of 2.36 g (10 mmol) 1,4-dibromobenzene in 200 ml absolute THF, cooled to -78 ° C., was added dropwise with 25.9 ml (44 mmol) of a 1.7 M solution of tet ⁇ f-butyllithium in n-hexane were added so that the temperature of the reaction mixture did not exceed -65 ° C.
- Example 2 Synthesis of 1,3-bis (dimesitylboryl) benzene A well-stirred solution of 2.36 g (10 mmol) of 1,3-dibromobenzene in 200 ml of absolute THF, cooled to -78 ° C., was added dropwise with 25.9 ml (44 mmol) of a 1.7 M solution of tert-butyllithium in n-hexane were added so that the temperature of the reaction mixture did not exceed -65 ° C. The solution was stirred at -78.degree. C.
- the yellow crude product (approx. 8 g, purity according to HPLC: 70-75% strength) was repeatedly recrystallized from ethyl acetate / t? -Hexane until a purity of 99.8% was reached by HPLC.
- the yield - with a purity of 99.8% according to HPLC - was 4.4 g corresponding to 53.4%.
- reaction mixture did not exceed -65 ° C.
- the reaction mixture was left under
- Example 4 Synthesis of 4,4 '-bis (dimesitylboryl) biphenyl To a cooled to -78 ° C, well-stirred suspension of 12.3 g (10 mmol) 4,4' - dibromobiphenyl in 200 ml of absolute THF was added dropwise over 20 min so 28.5 ml (48 mmol) of a UM solution of fe / t-butyllithium in n-hexane were added so that the temperature of the reaction mixture did not exceed -65 ° C. The suspension was stirred at -78 ° C.
- the desiccant was filtered off and the organic phase was evaporated to dryness.
- the yellow crude product (approx. 5.7 g, purity according to HPLC: 96-97%) was repeatedly recrystallized from chloroform or ethyl acetate / ethanol until a
- LEDs were produced using the general process outlined below. In individual cases, of course, this had to be adapted to the respective circumstances (e.g. layer thickness variation in order to achieve optimum efficiency or color).
- ITO-coated substrates e.g. glass substrates, PET film
- the ITO-coated substrates e.g. glass substrates, PET film
- Ultrasonic bath cleaned e.g. soap solution, Millipore water, isopropanol.
- Treated ozone plasma device for about 20 minutes. It may be advisable to use a polymer hole injection layer as the first organic layer.
- a conjugated, conductive polymer such as. B. a polyaniline derivative (PANI) or a polythiophene derivative (z. B. PEDOT from BAYER). This is then through
- the organic layers are deposited one after the other by vapor deposition
- the layer thickness of the respective Layer and the evaporation rate exactly tracked or set via a quartz crystal.
- individual layers can also consist of more than one connection, i. H. usually a host material with a guest material. This is achieved by co-evaporation from two or more sources.
- Electrodes are also applied to the organic layers. This is usually done by thermal evaporation (Balzer BA360 or Pfeiffer PL S 500). Then the transparent ITO electrode as the anode and the metal electrode (eg Ca, Yb, Ba-Al) as the cathode are contacted and the device parameters are determined.
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP01984879A EP1346421A1 (de) | 2000-12-22 | 2001-12-20 | Verwendung von bor- und aluminium-verbindungen in elektronik-bauteilen |
US10/250,594 US7060369B2 (en) | 2000-12-22 | 2001-12-20 | Use of boron and aluminum compounds in electronic components |
KR1020037008201A KR100832765B1 (ko) | 2000-12-22 | 2001-12-20 | 전자 부품에서의 붕소 및 알루미늄 화합물의 용도 |
JP2002553254A JP2005501372A (ja) | 2000-12-22 | 2001-12-20 | ホウ素化合物及びアルミニウム化合物を電子部品の中に使用する方法 |
US11/436,854 US7279603B2 (en) | 2000-12-22 | 2006-05-18 | Boron and aluminum compounds in electronic components |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP00128296.1 | 2000-12-22 | ||
EP00128296A EP1217668A1 (de) | 2000-12-22 | 2000-12-22 | Verwendung von Bor- und Aluminium-Verbindungen in Elektronik-Bauteilen |
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US10250594 A-371-Of-International | 2001-12-20 | ||
US11/436,854 Continuation US7279603B2 (en) | 2000-12-22 | 2006-05-18 | Boron and aluminum compounds in electronic components |
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US (2) | US7060369B2 (de) |
EP (2) | EP1217668A1 (de) |
JP (1) | JP2005501372A (de) |
KR (1) | KR100832765B1 (de) |
CN (1) | CN100428522C (de) |
WO (1) | WO2002052661A1 (de) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004095598A2 (en) * | 2003-04-21 | 2004-11-04 | The Trustees Of Princeton University | Organic light emitting devices with wide gap host materials |
WO2005057680A1 (en) * | 2003-12-05 | 2005-06-23 | Eastman Kodak Company | Organic element for electroluminescent devices |
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 |
WO2006117052A1 (de) * | 2005-05-03 | 2006-11-09 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtung und in deren herstellung verwendete boronsäure- und borinsäure-derivate |
JPWO2005062675A1 (ja) * | 2003-12-24 | 2007-12-13 | 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 |
JP2008177559A (ja) * | 2007-12-21 | 2008-07-31 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子及び表示装置 |
WO2012013271A1 (de) | 2010-07-30 | 2012-02-02 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtung |
EP3904361A2 (de) | 2013-10-02 | 2021-11-03 | Merck Patent GmbH | Borenthaltende verbindungen |
Families Citing this family (37)
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 |
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WO2004095598A2 (en) * | 2003-04-21 | 2004-11-04 | The Trustees Of Princeton University | Organic light emitting devices with wide gap host materials |
WO2004095598A3 (en) * | 2003-04-21 | 2005-05-19 | Univ Princeton | 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 |
WO2005057680A1 (en) * | 2003-12-05 | 2005-06-23 | Eastman Kodak Company | Organic element for electroluminescent devices |
US7074502B2 (en) | 2003-12-05 | 2006-07-11 | Eastman Kodak Company | Organic element for electroluminescent devices |
JPWO2005062675A1 (ja) * | 2003-12-24 | 2007-12-13 | 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 |
WO2006117052A1 (de) * | 2005-05-03 | 2006-11-09 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtung und in deren herstellung verwendete boronsäure- und borinsäure-derivate |
US8674141B2 (en) | 2005-05-03 | 2014-03-18 | Merck Patent Gmbh | Organic electroluminescent device and boric acid and borinic acid derivatives used therein |
US9403849B2 (en) | 2005-05-03 | 2016-08-02 | Merck Patent Gmbh | Organic electroluminescent device and boric acid and borinic acid derivatives used therein |
US9871213B2 (en) | 2005-05-03 | 2018-01-16 | Merck Patent Gmbh | Organic electroluminescent device |
JP2008177559A (ja) * | 2007-12-21 | 2008-07-31 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子及び表示装置 |
WO2012013271A1 (de) | 2010-07-30 | 2012-02-02 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtung |
EP3904361A2 (de) | 2013-10-02 | 2021-11-03 | Merck Patent GmbH | Borenthaltende verbindungen |
Also Published As
Publication number | Publication date |
---|---|
US7060369B2 (en) | 2006-06-13 |
EP1217668A1 (de) | 2002-06-26 |
CN1554127A (zh) | 2004-12-08 |
JP2005501372A (ja) | 2005-01-13 |
US7279603B2 (en) | 2007-10-09 |
EP1346421A1 (de) | 2003-09-24 |
US20040058194A1 (en) | 2004-03-25 |
US20060241321A1 (en) | 2006-10-26 |
KR20030077556A (ko) | 2003-10-01 |
KR100832765B1 (ko) | 2008-05-27 |
CN100428522C (zh) | 2008-10-22 |
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