JP6461326B2 - 有機電子素子の製造方法及び有機電子素子 - Google Patents
有機電子素子の製造方法及び有機電子素子 Download PDFInfo
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- JP6461326B2 JP6461326B2 JP2017517338A JP2017517338A JP6461326B2 JP 6461326 B2 JP6461326 B2 JP 6461326B2 JP 2017517338 A JP2017517338 A JP 2017517338A JP 2017517338 A JP2017517338 A JP 2017517338A JP 6461326 B2 JP6461326 B2 JP 6461326B2
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- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 1
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- LWYSGQKOCAQSIV-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)N(C1=CC=2C3(C4=CC(=CC=C4C2C=C1)N(C1=CC=CC2=CC=CC=C12)C1=CC=CC=C1)C1=CC(=CC=C1C=1C=CC(=CC13)N(C1=CC=CC3=CC=CC=C13)C1=CC=CC=C1)N(C1=CC=CC3=CC=CC=C13)C1=CC=CC=C1)C1=CC=CC=C1.C1=C(C=CC3=CC=CC=C13)N(C1=CC=C(C=C1)C1=CC=C(N(C3=CC2=CC=CC=C2C=C3)C3=CC2=CC=CC=C2C=C3)C=C1)C1=CC3=CC=CC=C3C=C1 Chemical compound C1(=CC=CC2=CC=CC=C12)N(C1=CC=2C3(C4=CC(=CC=C4C2C=C1)N(C1=CC=CC2=CC=CC=C12)C1=CC=CC=C1)C1=CC(=CC=C1C=1C=CC(=CC13)N(C1=CC=CC3=CC=CC=C13)C1=CC=CC=C1)N(C1=CC=CC3=CC=CC=C13)C1=CC=CC=C1)C1=CC=CC=C1.C1=C(C=CC3=CC=CC=C13)N(C1=CC=C(C=C1)C1=CC=C(N(C3=CC2=CC=CC=C2C=C3)C3=CC2=CC=CC=C2C=C3)C=C1)C1=CC3=CC=CC=C3C=C1 LWYSGQKOCAQSIV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- MEIZEZBPYQCCKI-UHFFFAOYSA-L FC=1C(=C(C(=C(C(=O)[O-])C1)C)F)F.FC=1C(=C(C(=C(C(=O)[O-])C1)C)F)F.[Cu+].[Cu+] Chemical compound FC=1C(=C(C(=C(C(=O)[O-])C1)C)F)F.FC=1C(=C(C(=C(C(=O)[O-])C1)C)F)F.[Cu+].[Cu+] MEIZEZBPYQCCKI-UHFFFAOYSA-L 0.000 description 1
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000007646 gravure printing 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
- 238000009776 industrial production Methods 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- FQHFBFXXYOQXMN-UHFFFAOYSA-M lithium;quinolin-8-olate Chemical compound [Li+].C1=CN=C2C([O-])=CC=CC2=C1 FQHFBFXXYOQXMN-UHFFFAOYSA-M 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- LBFXFIPIIMAZPK-UHFFFAOYSA-N n-[4-[4-(n-phenanthren-9-ylanilino)phenyl]phenyl]-n-phenylphenanthren-9-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C2=CC=CC=C2C=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C3=CC=CC=C3C=2)C=C1 LBFXFIPIIMAZPK-UHFFFAOYSA-N 0.000 description 1
- LKFCORSLOUZJMB-UHFFFAOYSA-N n-[4-[9-[4-(n-naphthalen-1-ylanilino)phenyl]fluoren-9-yl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 LKFCORSLOUZJMB-UHFFFAOYSA-N 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001894 space-charge-limited current method Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- WRTSXKKAXLYBSH-UHFFFAOYSA-N trifluoromethyl benzoate Chemical compound FC(F)(F)OC(=O)C1=CC=CC=C1 WRTSXKKAXLYBSH-UHFFFAOYSA-N 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07C63/70—Monocarboxylic acids
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- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic System
- C07F1/08—Copper compounds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60L—PROPULSION OF ELECTRICALLY-PROPELLED VEHICLES; SUPPLYING ELECTRIC POWER FOR AUXILIARY EQUIPMENT OF ELECTRICALLY-PROPELLED VEHICLES; ELECTRODYNAMIC BRAKE SYSTEMS FOR VEHICLES IN GENERAL; MAGNETIC SUSPENSION OR LEVITATION FOR VEHICLES; MONITORING OPERATING VARIABLES OF ELECTRICALLY-PROPELLED VEHICLES; ELECTRIC SAFETY DEVICES FOR ELECTRICALLY-PROPELLED VEHICLES
- B60L15/00—Methods, circuits, or devices for controlling the traction-motor speed of electrically-propelled vehicles
- B60L15/007—Physical arrangements or structures of drive train converters specially adapted for the propulsion motors of electric vehicles
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/94—Bismuth compounds
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- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
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- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02118—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer carbon based polymeric organic or inorganic material, e.g. polyimides, poly cyclobutene or PVC
- H01L21/0212—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer carbon based polymeric organic or inorganic material, e.g. polyimides, poly cyclobutene or PVC the material being fluoro carbon compounds, e.g.(CFx) n, (CHxFy) n or polytetrafluoroethylene
-
- H—ELECTRICITY
- H02—GENERATION; CONVERSION OR DISTRIBUTION OF ELECTRIC POWER
- H02M—APPARATUS FOR CONVERSION BETWEEN AC AND AC, BETWEEN AC AND DC, OR BETWEEN DC AND DC, AND FOR USE WITH MAINS OR SIMILAR POWER SUPPLY SYSTEMS; CONVERSION OF DC OR AC INPUT POWER INTO SURGE OUTPUT POWER; CONTROL OR REGULATION THEREOF
- H02M3/00—Conversion of dc power input into dc power output
- H02M3/02—Conversion of dc power input into dc power output without intermediate conversion into ac
- H02M3/04—Conversion of dc power input into dc power output without intermediate conversion into ac by static converters
- H02M3/10—Conversion of dc power input into dc power output without intermediate conversion into ac by static converters using discharge tubes with control electrode or semiconductor devices with control electrode
- H02M3/145—Conversion of dc power input into dc power output without intermediate conversion into ac by static converters using discharge tubes with control electrode or semiconductor devices with control electrode using devices of a triode or transistor type requiring continuous application of a control signal
- H02M3/155—Conversion of dc power input into dc power output without intermediate conversion into ac by static converters using discharge tubes with control electrode or semiconductor devices with control electrode using devices of a triode or transistor type requiring continuous application of a control signal using semiconductor devices only
- H02M3/156—Conversion of dc power input into dc power output without intermediate conversion into ac by static converters using discharge tubes with control electrode or semiconductor devices with control electrode using devices of a triode or transistor type requiring continuous application of a control signal using semiconductor devices only with automatic control of output voltage or current, e.g. switching regulators
- H02M3/158—Conversion of dc power input into dc power output without intermediate conversion into ac by static converters using discharge tubes with control electrode or semiconductor devices with control electrode using devices of a triode or transistor type requiring continuous application of a control signal using semiconductor devices only with automatic control of output voltage or current, e.g. switching regulators including plural semiconductor devices as final control devices for a single load
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- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
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- H10K50/15—Hole transporting layers
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- H10K71/164—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering using vacuum deposition
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- B60—VEHICLES IN GENERAL
- B60L—PROPULSION OF ELECTRICALLY-PROPELLED VEHICLES; SUPPLYING ELECTRIC POWER FOR AUXILIARY EQUIPMENT OF ELECTRICALLY-PROPELLED VEHICLES; ELECTRODYNAMIC BRAKE SYSTEMS FOR VEHICLES IN GENERAL; MAGNETIC SUSPENSION OR LEVITATION FOR VEHICLES; MONITORING OPERATING VARIABLES OF ELECTRICALLY-PROPELLED VEHICLES; ELECTRIC SAFETY DEVICES FOR ELECTRICALLY-PROPELLED VEHICLES
- B60L2210/00—Converter types
- B60L2210/10—DC to DC converters
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60L—PROPULSION OF ELECTRICALLY-PROPELLED VEHICLES; SUPPLYING ELECTRIC POWER FOR AUXILIARY EQUIPMENT OF ELECTRICALLY-PROPELLED VEHICLES; ELECTRODYNAMIC BRAKE SYSTEMS FOR VEHICLES IN GENERAL; MAGNETIC SUSPENSION OR LEVITATION FOR VEHICLES; MONITORING OPERATING VARIABLES OF ELECTRICALLY-PROPELLED VEHICLES; ELECTRIC SAFETY DEVICES FOR ELECTRICALLY-PROPELLED VEHICLES
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- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
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- Y02E10/549—Organic PV cells
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- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
- Y02T10/00—Road transport of goods or passengers
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- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
置換基R3は、1〜10個のC原子を含む、分枝した又は非分枝の、フッ化された又はフッ化されていない脂肪族炭化水素、アリール及びヘテロアリールを含む群から選択されていて、aは、0又は1であってよい]を示すことができる、本発明による方法に関する。
β−NPB (N,N′−ビス(ナフタレン−2−イル)−N,N′−ビス(フェニル)−ベンジジン)
TPD (N,N′−ビス(3−メチルフェニル)−N,N′−ビス(フェニル)−ベンジジン)
Spiro TPD (N,N′−ビス(3−メチルフェニル)−N,N′−ビス(フェニル)−ベンジジン)
Spiro−NPB (N,N′−ビス(ナフタレン−1−イル)−N,N′−ビス(フェニル)−スピロ)
DMFL−TPD (Ν,Ν′−ビス(3−メチルフェニル)−Ν,Ν′−ビス(フェニル)−9,9−ジメチル−フルオレン)
Ν,Ν′−ビス(ナフタレン−1−イル)−Ν,Ν′−ビス(フェニル)−2,2−ジメチルベンジジン
N,N′−ビス(3−メチルフェニル)−N,N′−ビス(フェニル)−9,9−スピロフルオレン
N,N′−ビス(ナフタレン−1−イル)−N,N′−ビス(フェニル)−9,9−スピロフルオレン
DMFL−NPB (Ν,Ν′−ビス(ナフタレン−1−イル)−Ν,Ν′−ビス(フェニル)−9,9−ジメチル−フルオレン)
DPFL−TPD (Ν,Ν′−ビス(3−メチルフェニル)−Ν,Ν′−ビス(フェニル)−9,9−ジフェニル−フルオレン)
DPFL−NPB (Ν,Ν′−ビス(ナフタレン−1−イル)−Ν,Ν′−ビス(フェニル)−9,9−ジフェニル−フルオレン)
Spiro−TAD (2,2′,7,7′−テトラキス(N,N−ジフェニルアミノ)−9,9′−スピロビフルオレン)
9,9−ビス[4−(N,N−ビス−ビフェニル−4−イル−アミノ)フェニル]−9H−フルオレン
9,9−ビス[4−(N,N−ビス−ナフタレン−2−イル−アミノ)フェニル]−9H−フルオレン
9,9−ビス[4−(N,N′−ビス−ナフタレン−2−イル−N,N′−ビス−フェニル−アミノ)−フェニル]−9H−フルオレン
N,N′−ビス(フェナントレン−9−イル)−N,N′−ビス(フェニル)−ベンジジン
2,7−ビス[N,N−ビス(9,9−スピロ−ビフルオレン−2−イル)−アミノ]−9,9−スピロ−ビフルオレン
2,2′−ビス[N,N−ビス(ビフェニル−4−イル)アミノ]9,9−スピロ−ビフルオレン
2,2′−ビス(N,N−ジ−フェニル−アミノ)9,9−スピロ−ビフルオレン
ジ−[4−(N,N−ジトリル−アミノ)−フェニル]シクロヘキサン
2,2′,7,7′−テトラ(N,N−ジ−トリル)アミノ−スピロ−ビフルオレン
N,N,N′,N′−テトラ−ナフタレン−2−イル−ベンジジン
2,2′,7,7′−テトラキス[N−ナフタレニル(フェニル)−アミノ]−9,9−スピロビフルオレン
Spiro−TTB (2,2′,7,7′−テトラキス−(Ν,Ν′−ジ−p−メチルフェニルアミノ)−9,9′−スピロビフルオレン)
酸化チタン−フタロシアニン
銅−フタロシアニン
2,3,5,6−テトラフルオロ−7,7,8,8−テトラシアノ−キノジメタン
4,4′,4″−トリス(Ν−3−メチルフェニル−N−フェニル−アミノ)トリフェニルアミン
4,4′,4″−トリス(N−(2−ナフチル)−N−フェニル−アミノ)トリフェニルアミン
4,4′,4″−トリス(N−(1−ナフチル)−N−フェニル−アミノ)トリフェニルアミン
4,4′,4″−トリス(N,N−ジフェニル−アミノ)トリフェニルアミン
ピラジノ[2,3−f][1,10]フェナントロリン−2,3−ジカルボニトリル
Ν,Ν,Ν′,Ν′−テトラキス(4−メトキシフェニル)ベンジジン
典型的な導電性材料は、この場合、次のものである:
2,2′,2″−(1,3,5−ベンゼントリイル)トリス(1−フェニル−1−H−ベンズイミダゾール)
2−(4−ビフェニリル)−5−(4−tert−ブチルフェニル)−1,3,4−オキサジアゾール
2,9−ジメチル−4,7−ジフェニル−1,10−フェナントロリン
8−ヒドロキシキノリノラト−リチウム
4−(ナフタレン−1−イル)−3,5−ジフェニル−4H−1,2,4−トリアゾール
1,3−ビス[2−(2,2′−ビピリジン−6−イル)−1,3,4−オキサジアゾ−5−イル]ベンゼン
4,7−ジフェニル−1,10−フェナントロリン
3−(4−ビフェニリル)−4−フェニル−5−tert−ブチルフェニル−1,2,4−トリアゾール
ビス(2−メチル−8−キノリノラート)−4−(フェニルフェノラト)アルミニウム
6,6′−ビス[5−(ビフェニル−4−イル)−1,3,4−オキサジアゾ−2−イル]−2,2′−ビピリジル
2−フェニル−9,10−ジ(ナフタレン−2−イル)−アントラセン
2,7−ビス[2−(2,2′−ビピリジン−6−イル)−1,3,4−オキサジアゾ−5−イル]−9,9−ジメチルフルオレン
1,3−ビス[2−(4−tert−ブチルフェニル)−1,3,4−オキサジアゾ−5−イル]ベンゼン
2−(ナフタレン−2−イル)−4,7−ジフェニル−1,10−フェナントロリン
2,9−ビス(ナフタレン−2−イル)−4,7−ジフェニル−1,10−フェナントロリン
トリス(2,4,6−トリメチル−3−(ピリジン−3−イル)フェニル)ボラン
1−メチル−2−(4−(ナフタレン−2−イル)フェニル)−1H−イミダゾ[4,5−f][1,10]フェナントロリン。
置換基R3は、1〜10個のC原子を含む、分枝した又は非分枝の、フッ化された又はフッ化されていない脂肪族炭化水素、アリール及びヘテロアリールを含む群から選択され、aは、0又は1であってよい]を示すことができる。
実施例Iは、金属錯体の銅(I)ビス−トリフルオロメチルベンゾアート(以後、Cu(3,5−tfmb)と省略する)に関する。
実施例IIは、金属錯体が、ビスマス(III)−トリス−3,5−トリフルオロメチルベンゾアート(以後、Bi(3,5−tfmb)3と省略する)である、本発明による方法に関する。
反応式1:
表1:それぞれの物質のアンプル試験の後に分離したアンプルの2つの異なる場所(場所A、場所B)に関する元素分析による炭素含有率の測定。
参考例Iは、気相堆積のための金属錯体としての、ビスマス(III)−トリス(2,6−ジフルオロベンゾアート)(略してBi(2,6−dfb)3)の使用に関する。
参考例IIは、気相堆積のための金属錯体としての、ビスマス(III)−トリス(4−フルオロベンゾアート)(略してBi(4−fb)3)の使用に関する。
参考例IIIは、気相堆積のための金属錯体としての、ビスマス(III)−トリス(3−フルオロベンゾアート)(略してBi(3−fb)3)の使用に関する。
参考例IVは、気相堆積のための金属錯体としての、ビスマス(III)−トリス(3,5−ジフルオロベンゾアート)(略してBi(3,5−dfb)3)の使用に関する。
参考例Vは、気相堆積のための金属錯体としての、ビスマス(III)−トリス(3,4,5−トリフルオロベンゾアート)(略してBi(3,4,5−tfb)3)の使用に関する。
参考例VIは、気相堆積のための金属錯体としての、ビスマス(III)−トリス(ペルフルオロベンゾアート)(略してBi(pfb)3)の使用に関する。
Bi(pfb)3でドープされた有機層の電気特性を、図19、20及び表14、15にまとめる。
参考例VIIは、気相堆積のための金属錯体としての、ビスマス(III)−トリス(4−ペルフルオロトルアート)(略してBi(4−pftl)3)の使用に関する。
参考例VIIIは、気相堆積のための金属錯体としての、ビスマス(III)−トリス(トリフルオロアセタート)(略してBi(tfa)3)の使用に関する。この製造は文献に記載されている(例えば、Suzuki, H.;Matano, Y.、Organobismut Chemistry、Elsevier 2001)。
参考例IXは、気相堆積のための金属錯体としての、ビスマス(III)−トリス(トリアセタート)(略してBi(ac)3)の使用に関する。この錯体は市場で入手可能である。
Claims (14)
- 有機電子素子の製造方法であって、前記素子は、マトリックスを含む少なくとも1つの有機電子層を備え、前記マトリックスは、ドーパントとして金属錯体を含み、前記金属錯体は、少なくとも1つの金属原子Mと、金属原子Mと結合する少なくとも1つの配位子Lとを含有し、前記配位子Lは、互いに無関係に、次の構造:
置換基R1は、互いに無関係に、1〜10個のC原子を有する、分枝された又は非分枝の、フッ化された脂肪族炭化水素を含む群から選択されていて、ここで、n=1〜5であり;かつ
置換基R2は、互いに無関係に、−CN、1〜10個のC原子を有する、分枝された又は非分枝の脂肪族炭化水素、アリール及びヘテロアリールを含む群から選択されていて、ここで、m=0〜最大5−nである]を示し、
前記配位子Lが、互いに無関係に、次の配位の形
前記金属錯体の金属原子Mは、Bi又はCuであり;
ここで、前記少なくとも1つの有機電子層のドーパントの堆積は、蒸発源を用いた気相堆積によって行われ、ここで、前記蒸発源は、前記ドーパントが、前記蒸発源の少なくとも1つの壁部と衝突を起こすように構成されている、前記有機電子素子の製造方法。 - 前記気相堆積は、線蒸発源を用いて行われる、請求項1に記載の方法。
- 置換基R1の少なくとも1つが、−CF3基である、請求項1又は2に記載の方法。
- 前記配位子Lは、正確に2つの置換基R1を備え、置換基R1はそれぞれ−CF3基を形成する、請求項1から3までのいずれか1項に記載の方法。
- 前記配位子Lは、正確に2つの置換基R1を備え、置換基R1は、それぞれ−CF3基を形成し、かつ配位子Lのベンゼン環の3,5位置に配置されている、請求項1から4までのいずれか1項に記載の方法。
- 置換基R2は、互いに無関係に、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基、tert−ブチル基、及び置換された又は非置換のフェニル基を含む群から選択されている、請求項1から5までのいずれか1項に記載の方法。
- 前記金属錯体は、ビスマス錯体であり、かつLは次の一般構造:
置換基R3は、1〜10個のC原子を有する、分枝された又は非分枝の、フッ化された又はフッ化されていない脂肪族炭化水素、アリール及びヘテロアリールを含む群から選択されている]を示すことができる、請求項1又は2に記載の方法。 - 前記配位子Lは、無関係に、
- 前記金属錯体は、前記金属錯体の昇華温度を10ケルビン超えるほど高い分解温度を示す、請求項1から8までのいずれか1項に記載の方法。
- 前記金属錯体は、前記金属錯体の昇華温度を40ケルビン超えるほど高い分解温度を示す、請求項1から9までのいずれか1項に記載の方法。
- 前記金属錯体は、前記金属錯体の昇華温度を70ケルビン超えるほど高い分解温度を示す、請求項1から10までのいずれか1項に記載の方法。
- 少なくとも1つの有機電子層を備えた有機電子素子において、前記有機電子層は、正孔輸送層であり、かつマトリックスを含み、前記マトリックスは、ドーパントとしてビスマス錯体を含み、前記ビスマス錯体は、ビスマス原子に結合した少なくとも1つの配位子Lを備え、配位子Lは、互いに無関係に、次の一般構造:
置換基R3は、1〜10個のC原子を有する、分枝された又は非分枝の、フッ化された又はフッ化されていない脂肪族炭化水素、アリール及びヘテロアリールを含む群から選択されていて、ここで、aは、0又は1であってもよい]を示すことができ、
前記配位子Lは、Biに1つの酸素原子で配位されているか、Biに両方の酸素原子で配位されているか、又はそれぞれ1つのBiに1つの酸素原子で配位されている、有機電子素子。 - Lは、無関係に、
- 前記ビスマス錯体は、錯体
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JP6562975B2 (ja) | 2019-08-21 |
DE202014106226U1 (de) | 2015-10-28 |
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EP3201959A1 (de) | 2017-08-09 |
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KR102167567B1 (ko) | 2020-10-19 |
US20210198285A1 (en) | 2021-07-01 |
US11040988B2 (en) | 2021-06-22 |
CN107078214B (zh) | 2020-10-02 |
US20170327516A1 (en) | 2017-11-16 |
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