JP4652365B2 - マトリックス材料とドーピング材料とからなる混合物、及び、ドーピングされた有機材料からなる層の製造方法 - Google Patents
マトリックス材料とドーピング材料とからなる混合物、及び、ドーピングされた有機材料からなる層の製造方法 Download PDFInfo
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- JP4652365B2 JP4652365B2 JP2007075684A JP2007075684A JP4652365B2 JP 4652365 B2 JP4652365 B2 JP 4652365B2 JP 2007075684 A JP2007075684 A JP 2007075684A JP 2007075684 A JP2007075684 A JP 2007075684A JP 4652365 B2 JP4652365 B2 JP 4652365B2
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- doping
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- 239000000463 material Substances 0.000 title claims description 85
- 239000011159 matrix material Substances 0.000 title claims description 57
- 238000004519 manufacturing process Methods 0.000 title claims description 42
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- 239000011368 organic material Substances 0.000 title claims description 9
- 238000001704 evaporation Methods 0.000 claims description 44
- 230000008020 evaporation Effects 0.000 claims description 43
- 239000002019 doping agent Substances 0.000 claims description 37
- 239000002243 precursor Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 15
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- 230000009467 reduction Effects 0.000 claims description 12
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- 238000000034 method Methods 0.000 claims description 8
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- 229920000642 polymer Polymers 0.000 claims description 5
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- 150000002390 heteroarenes Chemical class 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 150000005041 phenanthrolines Chemical class 0.000 claims description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 3
- VZRPHUITQPEYEY-UHFFFAOYSA-N 1,2,3-trimethyl-2-(1,2,3-trimethylbenzimidazol-2-yl)benzimidazole Chemical group CN1C2=CC=CC=C2N(C)C1(C)C1(C)N(C)C2=CC=CC=C2N1C VZRPHUITQPEYEY-UHFFFAOYSA-N 0.000 claims description 2
- 150000003248 quinolines Chemical class 0.000 claims description 2
- ORLFCYGPBAWFTH-UHFFFAOYSA-N 1,2,3-trimethyl-4,5-diphenyl-2-(1,2,3-trimethyl-4,5-diphenylimidazol-2-yl)imidazole Chemical compound CN1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N(C)C1(C)C(N1C)(C)N(C)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 ORLFCYGPBAWFTH-UHFFFAOYSA-N 0.000 claims 1
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- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
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- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 5
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- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 3
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- 125000000753 cycloalkyl group Chemical group 0.000 description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 2
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- BOXSCYUXSBYGRD-UHFFFAOYSA-N cyclopenta-1,3-diene;iron(3+) Chemical compound [Fe+3].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 BOXSCYUXSBYGRD-UHFFFAOYSA-N 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 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 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
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- 150000003839 salts Chemical class 0.000 description 2
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- 239000000126 substance Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- GVPZSYRAEBIWEP-UHFFFAOYSA-N 5,8-bis(methylcarbamoyl)naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)NC)=CC=C(C(=O)NC)C2=C1C(O)=O GVPZSYRAEBIWEP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- APLQAVQJYBLXDR-UHFFFAOYSA-N aluminum quinoline Chemical compound [Al+3].N1=CC=CC2=CC=CC=C12.N1=CC=CC2=CC=CC=C12.N1=CC=CC2=CC=CC=C12 APLQAVQJYBLXDR-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000003975 aryl alkyl amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 125000002228 disulfide group Chemical group 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- 125000005296 thioaryloxy group Chemical group 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000005106 triarylsilyl group Chemical group 0.000 description 1
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- H10K71/30—Doping active layers, e.g. electron transporting layers
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/20—Two benzimidazolyl-2 radicals linked together directly or via a hydrocarbon or substituted hydrocarbon radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/107—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with two aryl or substituted aryl radicals attached in positions 2 and 5
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H05B33/00—Electroluminescent light sources
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- H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
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- H10K85/649—Aromatic compounds comprising a hetero atom
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- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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Description
従来、半導体材料に対してドーピング材料を加えることで、例えば、有機発光ダイオード(OLED)などを実現することが知られている。これに伴い、ドーピング材料を加えた半導体はさまざまな性質の層に区分される。電荷輸送層にするには、強力なドナー化合物あるいは、アクセプター化合物を添加する。これにより、マトリックス材料とドーピング材料との間の電荷輸送体によって、上述の層における電子または正孔の導電率を大幅に高めることが可能となる。したがって、わずかな使用電圧で必要とされる一定の明るさを実現できるまでに、有機発光ダイオードの電気的な性質を改善することが可能となる。それ以上に、さらに多数の利点(例えば、電極からの電荷注入が改善されるなどの利点)を生み出すためには、したがって、さらにどのような物質を選択するかが問題になる。さらに、上記輸送層の抵抗損によって部材の機能が損なわれることのないように、広範囲にドーピング材料を追加した層厚を可変にする必要がある。例えば、層厚を選択可能にすれば、部材にとって最適な導電性を有する干渉を介して、部材において発生した光を放射することができる。
(i)1つの半導体材料と1つのドーピング材料とを混合することによる予備ドープ(前ドープ)された材料の製造
(ii)予備ドープされた材料の真空容器中の1つの蒸発源での加熱による蒸発、及び、基板上への蒸気の堆積、及び
(iii)堆積した層のエネルギー付加による活性化
予備ドープされた材料の製造は、例えば、成分を固体の状態で混合してもよいし、溶液の状態で混合しその後溶媒を除去してもよい。好ましい形態としては、予備ドープされた材料は、特別な形態で用いられることが好ましい。例えば、予備ドープされた材料から、圧縮材(プレス加工品)を製造し、続く工程(ii)で用いることが好ましい。他の目的のためには、予備ドープされた材料は、粉末として用いることが好ましい場合がある。
nドープ可能なマトリックス材料として、特に、例えばアルミニウムのキノリン錯体または他の主要基金属(キノリンリガンドも置換されうる)を用いることができる。特に、マトリックス材料は、トリス(8‐ヒドロキシ‐キノリン)アルミニウムであってもよい。さらに、Oおよび/またはNドナー原子を有する他のアルミニウム錯体を用いてもよい場合もある。
マトリクス分子と、ポリマーマトリクス分子のモノマー単位とが≦1:1である、好ましくは1:2未満、特に好ましくは1:5未満または1:10未満の、ドーピング濃度を有するドーパントが存在していることが好ましい。このドーピング濃度は、1:1から、1:100000まで、特に1:5から1:10000まで、または、1:10から1:1000まで(例えば、1:10から1:100まで、または、1:25から1:50まで)であってもよいが、これに制限されるものではない。
上記したように、予備ドープされた材料を用いる場合、2つの問題点がある。以下の実施例は、できる限り類似した蒸発温度を有するマトリックス材料およびドーピング材料によって行われたことが好ましい。これにより、本発明の予備ドープされた材料および本発明の方法は、実際、2つの問題点(つまりドーパントとマトリクスとの化学反応)を解決することを示すことができる。しかし、この制限が上記他の解決策との組み合わせによって、本発明のドーピング材料とともに複数の他の伝達材料を予備ドープされた材料として用いることができるということは、当業者には明白である。
予備ドープされた材料ルブレン:D2を、1gのルブレンZn(ZnTPP)と、0.1gのD2とから生成した。
Claims (9)
- ドーピングされた有機物質からなる層の製造に用いられ、少なくとも一つのマトリクス材料と少なくとも一つのドーピング材料とからなる混合物であって、
上記ドーピング材料は、不活性のドーパント前駆体であり、
上記ドーピング材料は、ドーパントの、ダイマー、オリゴマー、ポリマー、ジスピロ化合物、又は多環式化合物から選択され、
活性化エネルギーの付与によって分解されることを特徴とする、混合物。 - 上記ドーパント前駆体が、1,2,3,1’,2’,3’‐ヘキサメチル‐2,3,2’,3’‐テトラヒドロ‐2,2’‐ビ‐1H‐ベンズイミダゾールまたは1,2,3,1’,2’,3’‐ヘキサメチル‐4,5,4’,5’‐テトラフェニル‐2,3,2’,3’‐テトラヒドロ‐2,2’‐ビ‐1H‐イミダゾールであることを特徴とする、請求項1に記載の混合物。
- 上記マトリクス材料として、電子輸送材料が選択されることを特徴とする、請求項1又は2に記載の混合物。
- 上記マトリクス材料は、キノリン錯体、フェナントロリン、複素芳香族化合物、メタルフタロシアニン錯体及び/又はバックミンスターフラーレンから選択されることを特徴とする、請求項3に記載の混合物。
- ドーパント前駆体化合物の酸化電位をV OX _ DP 、マトリクス材料の還元電位をV red _ Mat としたときに、V OX _ DP −V red _ Mat が0.05Vよりも大きいことを特徴とする請求項1ないし4のいずれか1項に記載の混合物。
- 基板の上にドーピングされた有機物質からなる層を堆積により製造する製造方法であって、
上記ドーピングされた有機物質が、少なくとも一つのマトリクス材料と、少なくとも一つのドーピング材料とを含んでいる方法であって、
請求項1ないし5のいずれか1項に記載の混合物が、共通の蒸発源にて蒸気相へ運ばれ、続いて基板上へ堆積され、
上記ドーピング材料は不活性のドーピング材料として用いられ、製造工程中に活性化されることを特徴とする、製造方法。 - 上記活性化は、光エネルギー、マイクロ波、超音波、熱エネルギー及び/又は電気エネルギーにより生じることを特徴とする、請求項6に記載の製造方法。
- 有機発光ダイオードのドープされた輸送層を作るために請求項6又は7に記載の製造方法を用いる、製造方法の使用。
- 太陽電池のドープされた輸送層を作るために請求項6又は7に記載の製造方法を用いる、製造方法の使用。
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EP06005687A EP1837926B1 (de) | 2006-03-21 | 2006-03-21 | Heterocyclisches Radikal oder Diradikal, deren Dimere, Oligomere, Polymere, Dispiroverbindungen und Polycyclen, deren Verwendung, organisches halbleitendes Material sowie elektronisches Bauelement |
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WO2007107356A1 (en) | 2007-09-27 |
US20100233844A1 (en) | 2010-09-16 |
DE102007014048A1 (de) | 2007-09-27 |
EP2008318B1 (en) | 2013-02-13 |
EP2008318A1 (en) | 2008-12-31 |
JP2007273978A (ja) | 2007-10-18 |
TWI353677B (en) | 2011-12-01 |
DE102007014048B4 (de) | 2013-02-21 |
TW200739980A (en) | 2007-10-16 |
KR20090025188A (ko) | 2009-03-10 |
US9065055B2 (en) | 2015-06-23 |
KR101361710B1 (ko) | 2014-02-10 |
JP2009530836A (ja) | 2009-08-27 |
JP5683104B2 (ja) | 2015-03-11 |
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