TWI718099B - 電荷輸送性清漆及電荷輸送性薄膜之製造方法 - Google Patents
電荷輸送性清漆及電荷輸送性薄膜之製造方法 Download PDFInfo
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- TWI718099B TWI718099B TW104122316A TW104122316A TWI718099B TW I718099 B TWI718099 B TW I718099B TW 104122316 A TW104122316 A TW 104122316A TW 104122316 A TW104122316 A TW 104122316A TW I718099 B TWI718099 B TW I718099B
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- Prior art keywords
- bis
- charge
- transporting
- naphthyl
- benzidine
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- 239000002966 varnish Substances 0.000 title claims abstract description 61
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- YERGTYJYQCLVDM-UHFFFAOYSA-N iridium(3+);2-(4-methylphenyl)pyridine Chemical compound [Ir+3].C1=CC(C)=CC=C1C1=CC=CC=N1.C1=CC(C)=CC=C1C1=CC=CC=N1.C1=CC(C)=CC=C1C1=CC=CC=N1 YERGTYJYQCLVDM-UHFFFAOYSA-N 0.000 description 1
- ZKYQRJXGGLVQML-UHFFFAOYSA-N iridium(3+);2-phenylpyridine Chemical compound [Ir+3].C1=CC=CC=C1C1=CC=CC=N1 ZKYQRJXGGLVQML-UHFFFAOYSA-N 0.000 description 1
- IZUQUDLUTSCHMX-UHFFFAOYSA-N iridium;1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 IZUQUDLUTSCHMX-UHFFFAOYSA-N 0.000 description 1
- UXTZGRFXOOOBPM-UHFFFAOYSA-N iridium;5-phenyl-1h-pyrazole Chemical compound [Ir].N1C=CC(C=2C=CC=CC=2)=N1 UXTZGRFXOOOBPM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- 229940031993 lithium benzoate Drugs 0.000 description 1
- LDJNSLOKTFFLSL-UHFFFAOYSA-M lithium;benzoate Chemical compound [Li+].[O-]C(=O)C1=CC=CC=C1 LDJNSLOKTFFLSL-UHFFFAOYSA-M 0.000 description 1
- GQCUGWCIKIYVOY-UHFFFAOYSA-M lithium;quinoline-8-carboxylate Chemical compound [Li+].C1=CN=C2C(C(=O)[O-])=CC=CC2=C1 GQCUGWCIKIYVOY-UHFFFAOYSA-M 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
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- NJWJVPXCXKIBJD-QURGRASLSA-N n,n-diphenyl-6-[(e)-2-[4-(n-phenylanilino)phenyl]ethenyl]naphthalen-2-amine Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1/C=C/C(C=C1C=C2)=CC=C1C=C2N(C=1C=CC=CC=1)C1=CC=CC=C1 NJWJVPXCXKIBJD-QURGRASLSA-N 0.000 description 1
- OKPMSRGLGBBULD-UHFFFAOYSA-N n,n-diphenyl-9,9'-spirobi[fluorene]-1-amine Chemical compound C1=CC=CC=C1N(C=1C=2C3(C4=CC=CC=C4C4=CC=CC=C43)C3=CC=CC=C3C=2C=CC=1)C1=CC=CC=C1 OKPMSRGLGBBULD-UHFFFAOYSA-N 0.000 description 1
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- RYZPDEZIQWOVPJ-UHFFFAOYSA-N n-naphthalen-1-yl-n-[4-[4-[naphthalen-1-yl(naphthalen-2-yl)amino]phenyl]phenyl]naphthalen-2-amine Chemical compound C1=CC=C2C(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C4=CC=CC=C4C=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=CC2=C1 RYZPDEZIQWOVPJ-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- MQZFZDIZKWNWFX-UHFFFAOYSA-N osmium(2+) Chemical compound [Os+2] MQZFZDIZKWNWFX-UHFFFAOYSA-N 0.000 description 1
- CDXVUROVRIFQMV-UHFFFAOYSA-N oxo(diphenoxy)phosphanium Chemical compound C=1C=CC=CC=1O[P+](=O)OC1=CC=CC=C1 CDXVUROVRIFQMV-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000734 polysilsesquioxane polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical group C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
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- CGFYHILWFSGVJS-UHFFFAOYSA-N silicic acid;trioxotungsten Chemical compound O[Si](O)(O)O.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 CGFYHILWFSGVJS-UHFFFAOYSA-N 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
- FVRNDBHWWSPNOM-UHFFFAOYSA-L strontium fluoride Chemical compound [F-].[F-].[Sr+2] FVRNDBHWWSPNOM-UHFFFAOYSA-L 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000005259 triarylamine group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XSVXWCZFSFKRDO-UHFFFAOYSA-N triphenyl-(3-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=C(C=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XSVXWCZFSFKRDO-UHFFFAOYSA-N 0.000 description 1
- DETFWTCLAIIJRZ-UHFFFAOYSA-N triphenyl-(4-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DETFWTCLAIIJRZ-UHFFFAOYSA-N 0.000 description 1
- LNQMQGXHWZCRFZ-UHFFFAOYSA-N triphenyl-[4-(4-triphenylsilylphenyl)phenyl]silane Chemical group C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 LNQMQGXHWZCRFZ-UHFFFAOYSA-N 0.000 description 1
- KIGXXTRUJYDDKP-UHFFFAOYSA-N triphenyl-[4-[4-(4-triphenylsilylphenyl)phenyl]phenyl]silane Chemical group C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 KIGXXTRUJYDDKP-UHFFFAOYSA-N 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-N zinc;quinolin-8-ol Chemical compound [Zn+2].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
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- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/30—Doping active layers, e.g. electron transporting layers
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- 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
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- 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]
- H10K50/17—Carrier injection layers
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Abstract
本發明的電荷輸送性清漆為包含電荷輸送性物質、摻雜劑物質與有機溶劑，且電荷輸送性物質為包含選自N,N’-二(1-萘基)聯苯胺、N,N’-二(2-萘基)聯苯胺及N-(1-萘基)-N’-(2-萘基)聯苯胺之至少1種，將該電荷輸送性清漆適用於電洞注入層之情形時，可賦予能實現耐久性為優異的有機EL元件的電荷輸送性薄膜。
Description
本發明為關於電荷輸送性清漆，更詳言之為關於包含N,N’-二萘基聯苯胺來作為電荷輸送性物質的電荷輸送性清漆。
有機電致發光(EL)元件為被期待於顯示器或照明等領域之實用化，以低電壓驅動、高輝度、高壽命等為目的，已開發出有關各式各樣的材料或元件構造。
有機EL元件中為使用複數的機能性薄膜，其中之一的電洞注入層，擔任陽極與電洞輸送層或發光層之電荷之授受，對於用以達成有機EL元件的低電壓驅動及高輝度而言扮演著重要之機能。
該電洞注入層之形成方法，大致可分為以蒸鍍法為代表的乾式製程，與以旋轉塗佈法為代表的濕式製程，將該等製程相比時，濕式製程之方面能有效率地製造大面積、平坦性高的薄膜，因而特別是在顯示器領域中較常使用濕式製程。
於如此般之狀況下，本發明人已開發出各種
包含苯胺衍生物來作為電荷輸送性物質的電荷輸送性清漆(參考專利文獻1~4)，特別是由包含指定的芳基二胺化合物與電子接受性摻雜劑的電荷輸送性清漆所得到的薄膜，藉由將該薄膜使用作為電洞注入層，發現可得到輝度特性等為優異的有機EL元件(專利文獻4)。
然而，有關電洞注入層用的濕式製程材料，經常被要求改善，具備有專利文獻4的薄膜的有機EL元件，於所謂的耐久性之方面具有改善之餘地。
[專利文獻1]國際公開第2006/025342號
[專利文獻2]國際公開第2008/032616號
[專利文獻3]國際公開第2010/058777號
[專利文獻4]國際公開第2013/042623號
本發明為有鑑於如此般情事所完成之發明，目的為提供一種電荷輸送性清漆，其係適用於電洞注入層之情形時，可賦予能實現耐久性為優異的有機EL元件的電荷輸送性薄膜。
本發明人為了達成上述目的經深入研究之結果發現，各種的芳基二胺化合物之中，特別是將N,N’-二萘基聯苯胺使用作為電荷輸送性物質所調製的電荷輸送性清漆，將由該電荷輸送性清漆所製作的薄膜適用於有機EL元件之電洞注入層之情形時，可得到耐久性為良好的有機EL元件，因而完成本發明。
即，本發明為提供下述之發明。
<1>.一種電荷輸送性清漆，其特徵係包含電荷輸送性物質、摻雜劑物質與有機溶劑，前述電荷輸送性物質為包含選自N,N’-二(1-萘基)聯苯胺、N,N’-二(2-萘基)聯苯胺及N-(1-萘基)-N’-(2-萘基)聯苯胺之至少1種。
<2>.如前述<1>記載之電荷輸送性清漆，其中，前述摻雜劑物質為包含芳基磺酸化合物作為必須成分。
<3>.如前述<1>或<2>記載之電荷輸送性清漆，其中，前述電荷輸送性物質為包含N,N’-二(1-萘基)聯苯胺。
<4>.如前述<2>或<3>記載之電荷輸送性清漆，其中，前述摻雜劑物為質進而包含雜多酸。
<5>.一種電荷輸送性薄膜，其特徵係使用前述<1>~<4>中任一項記載之電荷輸送性清漆而製作。
<6>.一種有機電致發光元件，其特徵係具有前述<5>記載之電荷輸送性薄膜。
<7>.如前述<6>記載之有機電致發光元件，其中，前述電荷輸送性薄膜為構成電洞注入層。
<8>.一種電荷輸送性薄膜之製造方法，其特徵係將前
述<1>~<4>中任一項記載之電荷輸送性清漆塗佈至基材上並使溶劑蒸發。
<9>.一種耐久性提升方法，其係有機電致發光元件之輝度之耐久性提升方法，所述有機電致發光元件為具有：陽極及陰極；與介於該等各極間的包含發光層、電洞注入層及電洞輸送層的複數的機能層，其特徵為，使用選自N,N’-二(1-萘基)聯苯胺、N,N’-二(2-萘基)聯苯胺及N-(1-萘基)-N’-(2-萘基)聯苯胺之至少1種來作為構成前述電洞注入層的電荷輸送性物質。
由本發明的電荷輸送性清漆所製作的薄膜為表現出高電荷輸送性，因而可適合使用作為以有機EL元件為首的電子裝置用薄膜，特別是藉由將該薄膜適用於有機EL元件的電洞注入層，可得到輝度之耐久性為優異的有機EL元件。
又，即使是使用旋轉塗佈法或隙縫塗佈法等可成膜為大面積的各種濕式製程，本發明的電荷輸送性清漆亦可再現性良好地製造電荷輸送性為優異的薄膜，因而亦可充分對應於近年有機EL元件領域之進展。
以下對於本發明更詳細地進行說明。
本發明相關的電荷輸送性清漆為包含電荷輸送性物質、摻雜劑物質與有機溶劑，電荷輸送性物質為包含選自N,N’-二(1-萘基)聯苯胺、N,N’-二(2-萘基)聯苯胺及N-(1-萘基)-N’-(2-萘基)聯苯胺之至少1種。
作為電荷輸送性物質，只要是包含上述3種類之至少任一種即可，但其中以N,N’-二(1-萘基)聯苯胺、N,N’-二(2-萘基)聯苯胺為合適，以N,N’-二(1-萘基)聯苯胺為更合適。
尚，作為本發明的電荷輸送性物質，亦可與N,N’-二萘基聯苯胺一起併用其以外的周知的電荷輸送性物質，該情形時，就所謂得到的有機EL元件之耐久性提升之點而言，N,N’-二萘基聯苯胺必須為電荷輸送性物質之主成分(超過50質量%)，較佳為全電荷輸送性物質之70質量%以上為N,N’-二萘基聯苯胺，又較佳為90質量%以上，更佳為100質量%。
基於如此般之理由，本發明之較佳樣態為，全電荷輸送性物質中，以包含N,N’-二(1-萘基)聯苯胺及N,N’-二(2-萘基)聯苯胺之至少任一方為70質量%以上為較佳，又較佳為90質量%以上，更佳為100質量%；本發明之更佳樣態為，全電荷輸送性物質中，以包含N,N’-二(1-萘基)聯苯胺為70質量%以上為較佳，又較佳為90質量%以上，更佳為100質量%。
又，本發明的電荷輸送性清漆為包含摻雜劑物質。
作為摻雜劑物質之具體例，舉例如雜多酸或芳基磺酸化合物，就具備由該清漆所得到的薄膜的有機EL元件之輝度之耐久性提升之觀點而言，作為摻雜劑物質較佳為包含芳基磺酸化合物來作為必須成分。
作為芳基磺酸化合物未特別限定者，可從以往周知物中予以適當選擇使用，例如，可適合使用國際公開第2006/025342號記載的芳基磺酸化合物、國際公開第2009/096352號記載的芳基磺酸化合物等。
其中，較佳為式(1)或(2)所表示的芳基磺酸化合物。
式(1)中，A1為表示O或S，較佳為O。
A2為表示萘環或蒽環，較佳為萘環。
A3為表示二~四價的全氟聯苯基，p為表示A1與A3之鍵結數，並滿足2≦p≦4之整數，較佳為A3為二價的全氟聯苯基，且p為2。
q為表示鍵結於A3的磺酸基數，並為滿足1≦q≦4之整數，以2為最合適。
式(2)中，A4~A8相互獨立表示為氫原子、鹵
素原子、氰基、碳數1~20之烷基、碳數1~20之鹵素化烷基、或碳數2~20之鹵素化烯基，A4~A8中至少3個為鹵素原子。
r為表示鍵結於萘環的磺酸基數，並為滿足1≦r≦4之整數，以2~4為較佳，以2為最合適。
作為鹵素原子，舉例如氟原子、氯原子、溴原子、碘原子等，較佳為氟原子。
作為碳數1~20之烷基，可為直鏈狀、分支鏈狀、環狀之任一者，列舉例如：甲基、乙基、n-丙基、異丙基、n-丁基、異丁基、s-丁基、t-丁基、n-戊基、n-己基、n-庚基、n-辛基、n-壬基、n-癸基等之碳數1~20之直鏈或分支鏈狀烷基；環丙基、環丁基、環戊基、環己基、環庚基、環辛基、環壬基、環癸基、雙環丁基、雙環戊基、雙環己基、雙環庚基、雙環辛基、雙環壬基、雙環癸基等之碳數3~20之環狀烷基等。
作為碳數1~20之鹵素化烷基，可舉例如上述碳數1~20之烷基中之至少1個氫原子為經鹵素原子所取代之基，該具體例方面，舉例如：三氟甲基、2,2,2-三氟乙基、1,1,2,2,2-五氟乙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、1,1,2,2,3,3,3-七氟丙基、4,4,4-三氟丁基、3,3,4,4,4-五氟丁基、2,2,3,3,4,4,4-七氟丁基、1,1,2,2,3,3,4,4,4-九氟丁基等。
作為碳數2~20之鹵素化烯基，可舉例如將下述碳數2~20之烯基中之至少1個氫原子為經鹵素原子所
取代之基，該碳數2~20之烯基可舉例如：乙烯基、n-1-丙烯基、n-2-丙烯基、1-甲基乙烯基、n-1-丁烯基、n-2-丁烯基、n-3-丁烯基、2-甲基-1-丙烯基、2-甲基-2-丙烯基、1-乙基乙烯基、1-甲基-1-丙烯基、1-甲基-2-丙烯基、n-1-戊烯基、n-1-癸烯基、n-1-二十烯基等；該具體例方面，舉例如：全氟乙烯基、全氟丙烯基(烯丙基)、全氟丁烯基等。
此等之中，A4~A8較佳為氫原子、鹵素原子、氰基、碳數1~10之烷基、碳數1~10之鹵素化烷基、或碳數2~10之鹵素化烯基，且A4~A8中至少3個為氟原子；更佳為氫原子、氟原子、氰基、碳數1~5之烷基、碳數1~5之氟化烷基、或碳數2~5之氟化烯基，且A4~A8中至少3個為氟原子；又更佳為氫原子、氟原子、氰基、碳數1~5之全氟烷基、或碳數1~5之全氟烯基，且A4、A5及A8為氟原子。
尚，所謂的全氟烷基，指烷基的全數氫原子為經氟原子所取代之基；所謂的全氟烯基，指烯基的全數氫原子為經氟原子所取代之基。
作為合適的芳基磺酸化合物之具體例可舉例如以下所示者，但不限定於此等。
若作為摻雜劑物質為使用芳基磺酸之情形時，該使用量相對於電荷輸送性物質1而言，以莫耳比計為0.05~15.0，較佳為0.10~10.0，又較佳為0.25~7.0，更佳為0.50~5.0，又更佳為0.75~3.0，藉由設定為此範圍，使用於有機EL元件之情形時，將可再現性良好地得到能賦予高輝度及高耐久性的電荷輸送性薄膜。即，如此般的電荷輸送性清漆，芳基磺酸化合物之物質量(MA)之對於電荷輸送性物質之物質量(MH)之比為滿足0.05≦MA/MH≦15.0，較佳為0.10≦MA/MH≦10.0，又較佳為0.25≦MA/MH≦7.0，更佳為0.50≦MA/MH≦5.0，又更佳為0.75≦MA/MH≦3.0。
本發明的電荷輸送性清漆中所使用的摻雜劑物質，如同上述，較佳為包含芳基磺酸化合物來作為必須成分，但為了試圖提升電荷輸送能等，除了芳基磺酸化合物以外，因應所需亦可包含其他的摻雜劑物質。
作為其他的摻雜劑物質，只要是可溶解於清漆中使用的至少一種溶劑者即可，沒有特別的限制，使電荷輸送性
物質及芳基磺酸化合物一起進行薄膜化之情形時，就表現出良好的相溶性而言，較佳為雜多酸。
所謂的雜多酸，代表性如式(B1)所示的Keggin型、或式(B2)所示的Dawson型之化學構造所表示，其係具有雜原子為位於分子中心之構造，為釩(V)、鉬(Mo)、鎢(W)等的氧酸之異聚酸、與異種元素之氧酸進行縮合而成的聚酸。如此的異種元素之氧酸方面，主要可舉例如矽(Si)、磷(P)、砷(As)的氧酸。
作為雜多酸之具體例，舉例如：磷鉬酸、矽鉬酸、磷鎢酸、矽鎢酸、磷鎢鉬酸等，此等可單獨使用，亦可組合2種以上使用。尚，在本發明使用的雜多酸，可作為市售品而取得，又，亦可藉由習知方法來予以合成。
特以，當與芳基磺酸化合物一起使用的雜多酸為1種類之情形時，該雜多酸較佳為磷鎢酸或磷鉬酸，以磷鎢酸為最適宜。又，當與芳基磺酸化合物一起使用的雜多酸為2種類以上之情形時，該等之一者，以磷鎢酸或磷鉬酸為佳，更佳為磷鎢酸。
尚，雜多酸在元素分析等的定量分析中，不論是來自
一般式所示之構造之元素數量為多或少，其可為以市售品而取得，或依據習知合成方法而適當合成者，皆可用於本發明。
即，例如一般的磷鎢酸為以化學式H3(PW12O40)‧nH2O，磷鉬酸為以化學式H3(PMo12O40)‧nH2O來分別表示，但在定量分析中，該式中的P(磷)、O(氧)或W(鎢)或Mo(鉬)的數量不論是多或是少，其可為以市售品而取得，或依據習知合成方法而適當合成者，皆可用於本發明。該情形時，本發明中規定的所謂的雜多酸之質量，非指合成物或市售品中之純粹的磷鎢酸之質量(磷鎢酸含量)，係指可以市售品取得形態及以習知合成法可純化形態中，包含在水合水或其他雜質等狀態之全質量。
使用雜多酸之情形時，相對於電荷輸送性物質1而言，以質量比計之雜多酸之使用量為0.5~30.0左右，較佳為1.0~20.0左右，又較佳為2.0~15.0左右，更佳為3.0~12.0左右，又更佳為4.0~11.0左右，藉由設定為此範圍，使用於有機EL元件之情形時，將可再現性良好地得到能賦予高輝度的電荷輸送性薄膜。即，如此般的電荷輸送性清漆，雜多酸之質量(WD)之對於電荷輸送性物質之質量(WH)之比為滿足0.5≦WD/WH≦30.0，較佳為1.0≦WD/WH≦20.0，又較佳為2.0≦WD/WH≦15.0，更佳為3.0≦WD/WH≦12.0，又更佳為4.0≦WD/WH≦11.0。
作為調製電荷輸送性清漆之際所使用的有機溶劑，可使用能良好地溶解電荷輸送性物質及摻雜劑物質
的高溶解性溶劑。
作為如此般的高溶解性溶劑，可列舉例如環己酮、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮、1,3-二甲基-2-咪唑啉酮、二乙二醇單甲基醚等的有機溶劑，但不限定於此等。該等溶劑可使用單獨1種或混合2種以上使用，該使用量相對於清漆中所使用的溶劑全體可設為5~100質量%。
尚，電荷輸送性物質及摻雜劑物質較佳為，均可完全溶解於上述溶劑，或形成均勻分散之狀態，又較佳為可完全溶解。
又，本發明中，藉由於清漆中使含有至少一種類的25℃下具有10~200mPa‧s，特別是35~150mPa‧s之黏度，且常壓(大氣壓)下沸點50~300℃，特別是150~250℃的高黏度有機溶劑，清漆之黏度之調整將變得容易，其結果，可再現性良好地賦予平坦性為高的薄膜且可因應所使用的塗佈方法來調製清漆。
作為高黏度有機溶劑，可列舉例如環己醇、乙二醇、乙二醇二縮水甘油醚、1,3-辛二醇、二乙二醇、二丙二醇、三乙二醇、三丙二醇、1,3-丁二醇、2,3-丁二醇、1,4-丁二醇、丙二醇、己二醇等，但不限定於該等。該等溶劑可單獨使用1種或混合2種以上使用。
相對於本發明的清漆中所使用的溶劑全體，高黏度有機溶劑之添加比例較佳為不析出固體之範圍內，不析出固體下之添加比例又以5~90質量%為佳。
更，以相對於基板的濕潤性的提升、溶劑的表面張力的調整、極性的調整、沸點的調整等之目的，亦可使其他的溶劑，相對於清漆所使用的溶劑全體而言為1~90質量%，較佳為以1~50質量%的比例來混合。
作為如此般的溶劑，可列舉例如丙二醇單甲基醚、乙二醇單丁基醚、二乙二醇二乙基醚、二乙二醇二甲基醚、二乙二醇單乙基醚乙酸酯、二乙二醇單丁基醚乙酸酯、二丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、二乙二醇單乙基醚、二丙酮醇、γ-丁內酯、乳酸乙酯、n-己基乙酸酯等，但不限定於此等。此等溶劑可單獨使用1種，或混合2種以上使用。
本發明的清漆之黏度，可因應製作的薄膜之厚度等或固形分濃度而予以適當設定，但通常為1~50mPa．s(25℃下)。
又，本發明之電荷輸送性清漆之固形分濃度，係考量清漆之黏度及表面張力等、或製作的薄膜之厚度等而予以適當設定，但通常為0.1~10.0質量%左右，就考量清漆之塗佈性之提升時，較佳為0.5~5.0質量%左右，更佳為1.0~3.0質量%左右。
藉由將上述說明的電荷輸送性清漆塗佈於基材上並燒成，可使電荷輸送性薄膜形成於基材上。
作為清漆之塗佈方法未特別限定，可舉例如浸漬法、旋轉塗佈法、轉印印刷法、輥塗法、刷毛塗佈法、噴墨法、噴霧法等，較佳為因應塗佈方法來調節清漆之黏度及
表面張力。
又，使用本發明的清漆時，燒成環境亦未特別限定，不僅是大氣環境，即使是在氮等的惰性氣體或真空中，亦可得到均勻成膜面及具有高電荷輸送性的薄膜。
燒成溫度，考量所得到的薄膜之用途、賦予所得到的薄膜之電荷輸送性之程度、溶劑之種類或沸點等，以在100~260℃左右之範圍內予以適當設定，但將所得到的薄膜作為有機EL元件之電洞注入層使用時，較佳為140~250℃左右，又較佳為145~240℃左右。
尚，於燒成之際，就使展現出更高的均勻成膜性，或使反應在基材上進行為目的下，亦可設以二階段以上的溫度變化，加熱可使用例如加熱板或烘箱等，只要使用適當的機器來進行即可。
電荷輸送性薄膜之膜厚未特別限定，當在有機EL元件內使用作為電洞注入層時，較佳為5~200nm。作為使膜厚變化之方法，如使清漆中的固形分濃度變化之方法、或使塗佈時基板上的溶液量變化之方法等。
使用本發明的電荷輸送性清漆來製作OLED元件時，作為使用材料或製作方法，可舉例如下述者，但不限定於此等。
使用的電極基板，以預先進行由洗劑、醇、純水等之液體洗淨使其淨化為佳，例如，陽極基板係以在使用前施行UV臭氧處理、氧-電漿處理等之表面處理為佳。但，當陽極材料為以有機物作為主成分時，亦可不施行表面處
理。
具有由本發明的電荷輸送性清漆所得之薄膜所構成之電洞注入層之OLED元件之製作方法之例則係如以下所述。
藉由上述之方法，於陽極基板上塗佈本發明的電荷輸送性清漆並燒成，而在電極上製作電洞注入層。將此導入真空蒸鍍裝置內，依序蒸鍍電洞輸送層、發光層、電子輸送層、電子輸送層/電洞阻礙層、陰極金屬而製成OLED元件。尚，因應所需，亦可在發光層與電洞輸送層之間設置電子阻礙層。
作為陽極材料，可舉出以銦錫氧化物(ITO)、銦鋅氧化物(IZO)所代表之透明電極，或以鋁所代表之金屬或此等之合金等所構成之金屬陽極，以施加有平坦化處理者為佳。亦可使用具有高電荷輸送性之聚噻吩衍生物或聚苯胺衍生物。
尚，作為構成金屬陽極的其他的金屬，列舉例如：鈧、鈦、釩、鉻、錳、鐵、鈷、鎳、銅、鋅、鎵、釔、鋯、鈮、鉬、釕、銠、鈀、鎘、銦、鈧、鑭、鈰、鐠、釹、鉕、釤、銪、釓、鋱、鏑、鈥、鉺、銩、鐿、鉿、鉈、鎢、錸、鋨、銥、鉑、金、鈦、鉛、鉍或該等之合金等，但不限定於該等。
作為形成電洞輸送層之材料，可舉出如：(三苯基胺)二聚物衍生物、[(三苯基胺)二聚物]螺二聚物(Spiro-TAD)、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-聯苯胺(α-
NPD)、N,N’-雙(萘-2-基)-N,N’-雙(苯基)-聯苯胺、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-聯苯胺、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-9,9-旋環雙芴、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-旋環雙芴、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-9,9-二甲基-茀、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-二甲基-茀、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-9,9-二苯基-茀、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-二苯基-茀、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-2,2’-二甲基聯苯胺、2,2’,7,7’-肆(N,N-二苯基胺基)-9,9-旋環雙芴(spirobifluorene)、9,9-雙[4-(N,N-雙-聯苯基-4-基-胺基)苯基]-9H-茀、9,9-雙[4-(N,N-雙-萘-2-基-胺基)苯基]-9H-茀、9,9-雙[4-(N-萘-1-基-N-苯基胺基)-苯基]-9H-茀、2,2’,7,7’-肆[N-萘基(苯基)-胺基]-9,9-旋環雙芴、N,N’-雙(菲-9-基)-N,N’-雙(苯基)-聯苯胺、2,2’-雙[N,N-雙(聯苯基-4-基)胺基]-9,9-旋環雙芴、2,2’-雙(N,N-二苯基胺基)-9,9-旋環雙芴、二-[4-(N,N-二(p-甲苯基)胺基)-苯基]環己烷、2,2’,7,7’-四(N,N-二(p-甲苯基))胺基-9,9-旋環雙芴、N,N,N’,N’-四-萘-2-基-聯苯胺、N,N,N’,N’-四-(3-甲基苯基)-3,3’-二甲基聯苯胺、N,N’-二(萘基)-N,N’-二(萘-2-基)-聯苯胺、N,N,N’,N’-四(萘基)-聯苯胺、N,N’-二(萘-2-基)-N,N’-二苯基聯苯胺-1,4-二胺、N1,N4-二苯基-N1,N4-二(m-甲苯基)苯基-1,4-二胺、N2,N2,N6,N6-四苯基萘-2,6-二胺、參(4-(喹啉-8-基)苯基)胺、2,2’-雙(3-(N,N-二(p-甲苯基)胺基)苯基)聯苯、4,4’,4”-參[3-甲基苯基(苯基)胺基]三苯基
胺(m-MTDATA)、4,4’,4”-參[1-萘(苯基)胺基]三苯基胺(1-TNATA)等之三芳基胺類、5,5”-雙-{4-[雙(4-甲基苯基)胺基]苯基}-2,2’：5’,2”-聯三噻吩(BMA-3T)等之寡噻吩類等。
作為形成發光層之材料，可舉出如：參(8-羥基喹啉)鋁(III)(Alq3)、雙(8-羥基喹啉)鋅(II)(Znq2)、雙(2-甲基-8-羥基喹啉)(p-苯基酚)鋁(III)(BAlq)、4,4’-雙(2,2-二苯基乙烯基)聯苯、9,10-二(萘-2-基)蒽、2-t-丁基-9,10-二(萘-2-基)蒽、2,7-雙[9,9-二(4-甲基苯基)-茀-2-基]-9,9-二(4-甲基苯基)茀、2-甲基-9,10-雙(萘-2-基)蒽、2-(9,9-旋環雙芴-2-基)-9,9-旋環雙芴、2,7-雙(9,9-旋環雙芴-2-基)-9,9-旋環雙芴、2-[9,9-二(4-甲基苯基)-茀-2-基]-9,9-二(4-甲基苯基)茀、2,2’-二芘基-9,9-旋環雙芴、1,3,5-參(芘-1-基)苯、9,9-雙[4-(芘基)苯基]-9H-茀、2,2’-聯(9,10-二苯基蒽)、2,7-二芘基-9,9-旋環雙芴、1,4-二(芘-1-基)苯、1,3-二(芘-1-基)苯、6,13-二(聯苯基-4-基)稠五苯、3,9-二(萘-2-基)苝、3,10-二(萘-2-基)苝、參[4-(芘基)-苯基]胺、10,10’-二(聯苯基-4-基)-9,9’-聯蒽、N,N’-二(萘-1-基)-N,N’-二苯基-[1,1’：4’,1”：4”,1’’’-quarter-苯基]-4,4’’’-二胺、4,4’-二[10-(萘-1-基)蒽-9-基]聯苯、二苯并{[f,f’]-4,4’,7,7’-四苯基}二茚并[1,2,3-cd：1’,2’,3’-lm]苝、1-(7-(9,9’-聯蒽-10-基)-9,9-二甲基-9H-茀-2-基)芘、1-(7-(9,9’-聯蒽-10-基)-9,9-二己基-9H-茀-2-基)芘、1,3-雙(咔唑-9-基)苯基)、1,3,5-參(咔唑-9-基)苯)、4,4’,4”-參(咔唑-9-基)三苯基
胺、4,4’-雙(咔唑-9-基)聯苯(CBP)、4,4’-雙(咔唑-9-基)-2,2’-二甲基聯苯、2,7-雙(咔唑-9-基)-9,9-二甲基茀、2,2’,7,7’-肆(咔唑-9-基)-9,9-旋環雙芴、2,7-雙(咔唑-9-基)-9,9-二(p-甲苯基)茀、9,9-雙[4-(咔唑-9-基)-苯基]茀、2,7-雙(咔唑-9-基)-9,9-旋環雙芴、1,4-雙(三苯基矽烷基)苯、1,3-雙(三苯基矽烷基)苯、雙(4-N,N-二乙基胺基-2-甲基苯基)-4-甲基苯基甲烷、2,7-雙(咔唑-9-基)-9,9-二辛基茀、4,4”-二(三苯基矽烷基)-p-聯三苯、4,4’-二(三苯基矽烷基)聯苯、9-(4-t-丁基苯基)-3,6-雙(三苯基矽烷基)-9H-咔唑、9-(4-t-丁基苯基)-3,6-雙三苯甲基-9H-咔唑、9-(4-t-丁基苯基)-3,6-雙(9-(4-甲氧基苯基)-9H-茀-9-基)-9H-咔唑、2,6-雙(3-(9H-咔唑-9-基)苯基)吡啶、三苯基(4-(9-苯基-9H-茀-9-基)苯基)矽烷、9,9-二甲基-N,N-二苯基-7-(4-(1-苯基-1H-苯并[d]咪唑-2-基)苯基)-9H-茀-2-胺、3,5-雙(3-(9H-咔唑-9-基)苯基)吡啶、9,9-旋環雙芴-2-基-二苯基-膦氧化物、9,9’-(5-(三苯基矽烷基)-1,3-伸苯基)雙(9H-咔唑)、3-(2,7-雙(二苯基磷醯基)-9-苯基-9H-茀-9-基)-9-苯基-9H-咔唑、4,4,8,8,12,12-六(p-甲苯基)-4H-8H-12H-12C-氮雜二苯并[cd,mn]芘、4,7-二(9H-咔唑-9-基)-1,10-啡啉、2,2’-雙(4-(咔唑-9-基)苯基)聯苯、2,8-雙(二苯基磷醯基)二苯并[b,d]噻吩、雙(2-甲基苯基)二苯基矽烷、雙[3,5-二(9H-咔唑-9-基)苯基]二苯基矽烷、3,6-雙(咔唑-9-基)-9-(2-乙基-己基)-9H-咔唑、3-(二苯基磷醯基)-9-(4-(二苯基磷醯基)苯基)-9H-咔唑、3,6-雙[(3,5-二苯基)苯基]-9-苯基咔唑等，
亦可藉由與發光性摻雜劑共蒸鍍而形成發光層。
作為發光性摻雜劑，可舉出如：3-(2-苯并噻唑)-7-(二乙基胺基)香豆素、2,3,6,7-四氫-1,1,7,7-四甲基-1H,5H,11H-10-(2-苯并噻唑)喹嗪[9,9a,1gh]香豆素、喹吖酮、N,N’-二甲基-喹吖酮、參(2-苯基吡啶)銥(III)(Ir(ppy)3)、雙(2-苯基吡啶)(乙醯丙酮酸酯)銥(III)(Ir(ppy)2(acac))、參[2-(p-甲苯基)吡啶]銥(III)(Ir(mppy)3)、9,10-雙[N,N-二(p-甲苯基)胺基]蒽、9,10-雙[苯基(m-甲苯基)胺基]蒽、雙[2-(2-羥基苯)苯并噻唑]鋅(II)、N10,N10,N10’,N10’-四(p-甲苯基)-9,9’-聯蒽-10,10’-二胺、N10,N10,N10’,N10’-四苯基-9,9’-聯蒽-10,10’-二胺、N10,N10’-二苯基-N10,,N10’-二萘基-9,9’-聯蒽-10,10’-二胺、4,4’-雙(9-乙基-3-咔唑乙烯基)-1,1’-聯苯、苝、2,5,8,11-四-t-丁基苝、1,4-雙[2-(3-N-乙基咔唑基)乙烯基]苯、4,4’-雙[4-(二-p-甲苯基胺基)苯乙烯基]聯苯、4-(二-p-甲苯基胺基)-4’-[(二-p-甲苯基胺基)苯乙烯基]茋、雙[3,5-二氟-2-(2-吡啶)苯基-(2-羧基吡啶]銥(III)、4,4’-雙[4-(二苯基胺基)苯乙烯基]聯苯、雙(2,4-二氟苯基吡啶)肆(1-吡唑基)硼酸銥(III)、N,N’-雙(萘-2-基)-N,N’-雙(苯基)-參(9,9-二甲基茀基)、2,7-雙{2-[苯基(m-甲苯基)胺基]-9,9-二甲基-茀-7-基}-9,9-二甲基-茀、N-(4-((E)-2-(6((E)-4-(二苯基胺基)苯乙烯基)萘-2-基)乙烯基)苯基)-N-苯基苯基胺、fac-銥(III)參(1-苯基-3-甲基苯并咪唑咻-2-亞基-C,C2’)、mer-銥(III)參(1-苯基-3-甲基苯并咪唑咻-2-亞基-C,C2’)、
2,7-雙[4-(二苯基胺基)苯乙烯基]-9,9-旋環雙芴、6-甲基-2-(4-(9-(4-(6-甲基苯并[d]噻唑-2-基)苯基)蒽-10-基)苯基)苯并[d]噻唑、1,4-二[4-(N,N-二苯基)胺基]苯乙烯基苯、1,4-雙(4-(9H-咔唑-9-基)苯乙烯基)苯、(E)-6-(4-(二苯基胺基)苯乙烯基)-N,N-二苯基萘-2-胺、雙(2,4-二氟苯基吡啶)(5-(吡啶-2-基)-1H-四氮唑)銥(III)、雙(3-三氟甲基-5-(2-吡啶)吡唑)((2,4-二氟苄基)二苯基膦酸酯)銥(III)、雙(3-三氟甲基-5-(2-吡啶)吡唑)(苄基二苯基膦酸酯)銥(III)、雙(1-(2,4-二氟苄基)-3-甲基苯并咪唑)(3-(三氟甲基)-5-(2-吡啶)-1,2,4-三唑酯)銥(III)、雙(3-三氟甲基-5-(2-吡啶)吡唑)(4’,6’-二氟苯基吡啶酯)銥(III)、雙(4’,6’-二氟苯基吡啶)(3,5-雙(三氟甲基)-2-(2’-吡啶)吡咯酯)銥(III)、雙(4’,6’-二氟苯基吡啶)(3-(三氟甲基)-5-(2-吡啶)-1,2,4-三唑酯)銥(III)、(Z)-6-
基-N-(6-
基喹啉-2(1H)-亞基)喹啉-2-胺-BF2、(E)-2-(2-(4-(二甲基胺基)苯乙烯基)-6-甲基-4H-喃-4-亞基)丙二腈、4-(二氰基亞甲基)-2-甲基-6-朱咯啶基(julolidinyl)-9-烯基-4H-喃、4-(二氰基亞甲基)-2-甲基-6-(1,1,7,7-四甲基朱咯啶基-9-烯基)-4H-喃、4-(二氰基亞甲基)-2-t-丁基-6-(1,1,7,7-四甲基朱咯啶基-4-基-乙烯基)-4H-喃、參(二苯并基甲烷)啡啉銪(III)、5,6,11,12-四苯基稠四苯、雙(2-苯并[b]噻吩-2-基-吡啶)(乙醯丙酮酸酯)銥(III)、參(1-苯基異喹啉)銥(III)、雙(1-苯基異喹啉)(乙醯丙酮酸酯)銥(III)、雙[1-(9,9-二甲基-9H-茀-2-基)-異喹啉](乙醯丙酮酸酯)銥(III)、雙[2-(9,9-二甲基-9H-茀-2-基)喹啉](乙醯
丙酮酸酯)銥(III)、參[4,4’-二-t-丁基-(2,2’)-聯吡啶]釕(III)‧雙(六氟磷酸酯)、參(2-苯基喹啉)銥(III)、雙(2-苯基喹啉)(乙醯丙酮酸酯)銥(III)、2,8-二-t-丁基-5,11-雙(4-t-丁基苯基)-6,12-二苯基稠四苯、雙(2-苯基苯并噻唑)(乙醯丙酮酸酯)銥(III)、5,10,15,20-四苯基四苯并卟啉白金、鋨(II)雙(3-三氟甲基-5-(2-吡啶)-吡唑)二甲基苯基膦、鋨(II)雙(3-(三氟甲基)-5-(4-t-丁基吡啶)-1,2,4-三唑酯)二苯基甲基膦、鋨(II)雙(3-(三氟甲基)-5-(2-吡啶)-1,2,4-三唑)二甲基苯基膦、鋨(II)雙(3-(三氟甲基)-5-(4-t-丁基吡啶)-1,2,4-三唑酯)二甲基苯基膦、雙[2-(4-n-己基苯基)喹啉](乙醯丙酮酸酯)銥(III)、參[2-(4-n-己基苯基)喹啉]銥(III)、參[2-苯基-4-甲基喹啉]銥(III)、雙(2-苯基喹啉)(2-(3-甲基苯基)吡啶酯)銥(III)、雙(2-(9,9-二乙基-茀-2-基)-1-苯基-1H-苯并[d]咪唑酯)(乙醯丙酮酸酯)銥(III)、雙(2-苯基吡啶)(3-(吡啶-2-基)-2H-苯并哌喃-2-酮)銥(III)、雙(2-苯基喹啉)(2,2,6,6-四甲基庚烷-3,5-二酮)銥(III)、雙(苯基異喹啉)(2,2,6,6-四甲基庚烷-3,5-二酮)銥(III)、銥(III)雙(4-苯基噻吩[3,2-c]吡啶-N,C2’)乙醯丙酮酸酯、(E)-2-(2-t-丁基-6-(2-(2,6,6-三甲基-2,4,5,6-四氫-1H-吡咯并[3,2,1-ij]喹啉-8-基)乙烯基)-4H-喃-4-亞基)丙二腈、雙(3-三氟甲基-5-(1-異喹啉基)吡唑)(甲基二苯基膦)釕、雙[(4-n-己基苯基)異喹啉](乙醯丙酮酸酯)銥(III)、白金(II)八乙基卟吩、雙(2-甲基二苯并[f，h]喹
啉)(乙醯丙酮酸酯)銥(III)、參[(4-n-己基苯基)氧代喹啉]銥(III)等。
作為形成電子輸送層/電洞阻礙層之材料，可舉出如：8-羥喹啉酸鹽-鋰、2,2’,2”-(1,3,5-苯甲苯基)-參(1-苯基-1-H-苯咪唑)、2-(4-聯苯基)5-(4-t-丁基苯基)-1,3,4-噁二唑、2,9-二甲基-4,7-二苯基-1,10-啡啉、4,7-二苯基-1,10-啡啉、雙(2-甲基-8-喹啉酸酯)-4-(苯基酚氧)鋁、1,3-雙[2-(2,2’-聯吡啶-6-基)-1,3,4-
二唑-5-基]苯、6,6’-雙[5-(聯苯基-4-基)-1,3,4-
二唑-2-基]-2,2’-聯吡啶、3-(4-聯苯基)-4-苯基-5-t-丁基苯基-1,2,4-三唑、4-(萘-1-基)-3,5-二苯基-4H-1,2,4-三唑、2,9-雙(萘-2-基)-4,7-二苯基-1,10-啡啉、2,7-雙[2-(2,2’-聯吡啶-6-基)-1,3,4-
二唑-5-基]-9,9-二甲基茀、1,3-雙[2-(4-t-丁基苯基)-1,3,4-
二唑-5-基]苯、參(2,4,6-三甲基-3-(吡啶-3-基)苯基)硼烷、1-甲基-2-(4-(萘-2-基)苯基)-1H-咪唑[4,5f][1,10]啡啉、2-(萘-2-基)-4,7-二苯基-1,10-啡啉、苯基-二芘基膦氧化物、3,3’,5,5’-四[(m-吡啶)-吩-3-基]聯苯、1,3,5-參[(3-吡啶)-吩-3-基]苯、4,4’-雙(4,6-二苯基-1,3,5-三嗪-2-基)聯苯、1,3-雙[3,5-二(吡啶-3-基)苯基]苯、雙(10-羥苯并[h]喹啉)鈹、二苯基雙(4-(吡啶-3-基)苯基)矽烷、3,5-二(芘-1-基)吡啶等。
作為形成電子注入層之材料，可舉出如氧化鋰(Li2O)、氧化鎂(MgO)、氧化鋁(Al2O3)、氟化鋰(LiF)、氟化鈉(NaF)、氟化鎂(MgF2)、氟化銫(CsF)、氟化鍶(SrF2)、三氧化鉬(MoO3)、鋁、Li(acac)、乙酸鋰、安息香酸鋰等。
作為陰極材料，可舉出如鋁、鎂-銀合金、鋁-鋰合金、鋰、鈉、鉀、銫等。
作為形成電子阻礙層之材料，可舉出如參(苯基吡唑)銥等。
使用本發明之電荷輸送性清漆之PLED元件之製作方法並無特別限定，可舉出如以下之方法。
上述OLED元件製作中，亦可取代電洞輸送層、發光層、電子輸送層、電子注入層之真空蒸鍍操作，藉由依序形成電洞輸送性高分子層、發光性高分子層，而可製成具有由本發明之電荷輸送性清漆所形成之電荷輸送性薄膜之PLED元件。
具體而言，於陽極基板上塗佈本發明之電荷輸送性清漆，藉由上述之方法製作電洞注入層，並於其上依序形成電洞輸送性高分子層、發光性高分子層後，再蒸鍍陰極而製成PLED元件。
作為使用之陰極及陽極材料，可使用與上述OLED元件製作時為相同者，亦可施行相同之洗淨處理、表面處理。
作為電洞輸送性高分子層及發光性高分子層之形成法，可舉出如在電洞輸送性高分子材料或發光性高分子材料、或於此等中添加摻雜劑物質之材料中添加溶劑使其溶解或均勻分散，塗佈於電洞注入層或電洞輸送性高分子層之上後，藉由使分別燒成來進行成膜之方法。
作為電洞輸送性高分子材料，可舉出如聚
[(9,9-二己基茀-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,4-二胺基伸苯基)]、聚[(9,9-二辛基茀-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,1’-亞聯苯基-4,4-二胺)]、聚[(9,9-雙{1’-戊烯-5’-基}茀-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,4-二胺基伸苯基)]、受聚倍半矽氧烷封端之聚[N,N’-雙(4-丁基苯基)-N,N’-雙(苯基)-聯苯胺]、聚[(9,9-貳二辛基茀-2,7-二基)-co-(4,4’-(N-(p-丁基苯基))二苯基胺)]等。
作為發光性高分子材料，可舉出如聚(9,9-二烷基茀)(PDAF)等之聚茀衍生物、聚(2-甲氧基-5-(2’-乙基己氧基)-1,4-苯基乙烯)(MEH-PPV)等之聚苯基乙烯衍生物、聚(3-烷基噻吩)(PAT)等之聚噻吩衍生物、聚乙烯基咔唑(PVCz)等。
作為溶劑，可舉出如甲苯、二甲苯、三氯甲烷等，作為溶解或均勻分散法，可舉出如攪拌、加熱攪拌、超音波分散等之方法。
作為塗佈方法未特別限定者，可舉出如噴墨法、噴霧法、浸漬法、旋轉塗佈法、轉印印刷法、輥塗法、刷塗法等。尚且，塗佈係以在氮、氬等之惰性氣體下進行為佳。
作為進行燒成之方法，可舉出在惰性氣體下或真空中，以烤箱或加熱板進行加熱之方法。
以下，例舉實施例及比較例，更具體地說明本發明，但本發明並不受到下述實施例所限定。尚且，使
用之裝置係如同下述。
(1)基板洗淨：長州產業(股)製 基板洗淨裝置(減壓電漿方式)
(2)清漆之塗佈：Mikasa(股)製 旋轉塗佈機MS-A100
(3)膜厚測定：(股)小坂研究所製 微細形狀測量機Surfcorder ET-4000
(4)EL元件之製作：長州產業(股)製 多機能蒸鍍裝置系統C-E2L1G1-N
(5)EL元件之輝度等之測定：(有)Tech World製 I-V-L測定系統
(6)EL元件之壽命測定(輝度之半衰期之測定)：(股)E etch Sea製 有機EL輝度壽命評價系統PEL-105S
於氮環境下，使N,N’-二(1-萘基)聯苯胺0.211g及式(A1)所表示的芳基磺酸0.218g溶解於1,3-二甲基-2-咪唑啉酮(以下稱為DMI)15g中。對此添加環己醇(以下稱為CHA)3.0g及丙二醇(以下稱為PG)3.0g並攪拌，來調製電荷輸送性清漆。
尚，式(A1)所表示的芳基磺酸為依據國際公開第2006/025342號之記載所合成(以下為相同)。
於氮環境下，使N,N’-二(1-萘基)聯苯胺0.143g、上述式(A1)所表示的芳基磺酸0.200g及磷鎢酸0.086g溶解於DMI 15g中。對此添加CHA 3.0g及PG 3.0g並攪拌，來調製電荷輸送性清漆。
除了使用N,N’-二苯基聯苯胺來取代N,N’-二(1-萘基)聯苯胺以外，與實施例1-2以相同方法來調製電荷輸送性清漆。
使用旋轉塗佈機將實施例1-1中得到的電荷輸送性清漆塗佈於ITO基板後，以80℃乾燥1分鐘，進而在大氣環境下，以230℃燒成15分鐘，而在ITO基板上形成30nm之均勻薄膜。ITO基板方面係使用於表面上銦錫氧化物(ITO)圖型化成膜厚150nm之25mm×25mm×0.7t之玻璃基板，且在使用前藉由O2電漿洗淨裝置(150W、30秒
間)去除表面上之雜質者。
接著，使用蒸鍍裝置(真空度1.0×10-5Pa)，於對形成有薄膜之ITO基板上依序層合N,N’-二(1-萘基)-N,N’-二苯基聯苯胺(α-NPD)、參(8-羥基喹啉)鋁(III)(Alq3)、氟化鋰、及鋁之薄膜，而得到有機EL元件。此時，蒸鍍速率係分別在α-NPD、Alq3及鋁時為0.2nm/秒，在氟化鋰時為0.02nm/秒之條件下來進行，膜厚係分別作成30nm、40nm、0.5nm及100nm。
尚且，為了防止因空氣中之氧、水等之影響所造成的特性劣化，有機EL元件係在藉由密封基板密封後評價該特性。密封係依據以下之順序施行。
在氧濃度2ppm以下、露點-85℃以下之氮環境中，在密封基板之間收納有機EL元件，並藉由接著材料((股)MORESCO製，MOISTURE CUT WB90US(P))貼合密封基板。此時，將捕水劑(Dynic(股)製HD-071010W-40)與有機EL元件一同地收納於密封基板內。對於已貼合之密封基板，照射UV光(波長：365nm、照射量：6,000mJ/cm2)後，在80℃下施行1小時退火處理而使接著材料硬化。
除了分別使用實施例1-2、比較例1所得到的清漆來取代實施例1-1所得到的清漆以外，與實施例2-1以相同之方法來製作有機EL元件。
對於上述實施例2-1及2-2所製作的元件，測定驅動電壓5V時的電流密度、輝度及電流效率。結果表示於表1中。
又，測定實施例2-1、2-2及比較例2所製作的元件之輝度之半衰期(初期輝度5000cd/m2)。結果表示於表2中。
如表1、2所示可得知般，藉由將由本發明的電荷輸送性清漆所得到的薄膜作為電洞注入層使用，可得到輝度之耐久性為優異的有機EL元件。
Claims (9)
- 一種電荷輸送性清漆，其特徵係包含電荷輸送性物質、摻雜劑物質與有機溶劑，前述電荷輸送性物質為包含選自N,N’-二(1-萘基)聯苯胺、N,N’-二(2-萘基)聯苯胺及N-(1-萘基)-N’-(2-萘基)聯苯胺之至少1種。
- 如請求項1記載之電荷輸送性清漆，其中，前述摻雜劑物質為包含芳基磺酸化合物作為必須成分。
- 如請求項1或2記載之電荷輸送性清漆，其中，前述電荷輸送性物質為包含N,N’-二(1-萘基)聯苯胺。
- 如請求項2記載之電荷輸送性清漆，其中，前述摻雜劑物質為進而包含雜多酸。
- 一種電荷輸送性薄膜，其特徵係使用請求項1~4中任一項記載之電荷輸送性清漆而製作。
- 一種有機電致發光元件，其特徵係具有請求項5記載之電荷輸送性薄膜。
- 如請求項6記載之有機電致發光元件，其中，前述電荷輸送性薄膜為構成電洞注入層。
- 一種電荷輸送性薄膜之製造方法，其特徵係將請求項1~4中任一項記載之電荷輸送性清漆塗佈至基材上並使溶劑蒸發。
- 一種耐久性提升方法，其係有機電致發光元件之輝度之耐久性提升方法，所述有機電致發光元件為具有：陽極及陰極；與介於該等各極間的包含發光層、電洞注入層及電洞輸 送層的複數的機能層，其特徵為，使用選自N,N’-二(1-萘基)聯苯胺、N,N’-二(2-萘基)聯苯胺及N-(1-萘基)-N’-(2-萘基)聯苯胺之至少1種來作為構成前述電洞注入層的電荷輸送性物質。
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| TWI447099B (zh) * | 2008-01-29 | 2014-08-01 | Nissan Chemical Ind Ltd | Aryl sulfonic acid compounds and the use of electron acceptables |
| KR100965044B1 (ko) * | 2008-06-03 | 2010-06-21 | 주식회사 두산 | 신규 실리콘계 화합물, 그 제조 방법 및 이를 이용한 유기발광 소자 |
| WO2010058777A1 (ja) | 2008-11-19 | 2010-05-27 | 日産化学工業株式会社 | 電荷輸送性材料および電荷輸送性ワニス |
| KR102212771B1 (ko) * | 2013-02-26 | 2021-02-05 | 닛산 가가쿠 가부시키가이샤 | 전하 수송성 바니시 |
| CN105190929B (zh) * | 2013-03-18 | 2017-05-10 | 日产化学工业株式会社 | 电荷传输性清漆 |
-
2015
- 2015-07-09 TW TW104122316A patent/TWI718099B/zh active
- 2015-07-10 US US15/325,194 patent/US20170186951A1/en not_active Abandoned
- 2015-07-10 EP EP15818414.3A patent/EP3168888A4/en not_active Withdrawn
- 2015-07-10 JP JP2016532977A patent/JPWO2016006673A1/ja active Pending
- 2015-07-10 CN CN201580037628.1A patent/CN106537629B/zh active Active
- 2015-07-10 WO PCT/JP2015/069821 patent/WO2016006673A1/ja active Application Filing
- 2015-07-10 KR KR1020177002531A patent/KR102430699B1/ko active IP Right Grant
-
2020
- 2020-07-20 JP JP2020123364A patent/JP7161507B2/ja active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5358788A (en) * | 1992-04-02 | 1994-10-25 | Idemitsu Kosan Company Limited | Organic electroluminescence device containing a silanamine compound |
| JP2002151272A (ja) * | 2000-11-09 | 2002-05-24 | Nissan Chem Ind Ltd | 電界発光素子 |
| TW200714679A (en) * | 2005-06-03 | 2007-04-16 | Nissan Chemical Ind Ltd | Charge-transporting varnishes containing charge-transporting polymers and organic electroluminescent devices made by using the same |
| TW201317273A (zh) * | 2011-09-21 | 2013-05-01 | Nissan Chemical Ind Ltd | 電荷輸送性清漆 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106537629B (zh) | 2019-03-29 |
| EP3168888A1 (en) | 2017-05-17 |
| US20170186951A1 (en) | 2017-06-29 |
| KR102430699B1 (ko) | 2022-08-09 |
| JP2020170876A (ja) | 2020-10-15 |
| WO2016006673A1 (ja) | 2016-01-14 |
| EP3168888A4 (en) | 2018-03-14 |
| KR20170029529A (ko) | 2017-03-15 |
| JP7161507B2 (ja) | 2022-10-26 |
| CN106537629A (zh) | 2017-03-22 |
| JPWO2016006673A1 (ja) | 2017-04-27 |
| TW201622200A (zh) | 2016-06-16 |
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