TW201711519A - 電荷輸送性膜之製造方法、電荷輸送性膜、有機電致發光元件、有機電致發光元件之製造方法、電荷輸送性膜之電荷輸送性提升方法 - Google Patents
電荷輸送性膜之製造方法、電荷輸送性膜、有機電致發光元件、有機電致發光元件之製造方法、電荷輸送性膜之電荷輸送性提升方法 Download PDFInfo
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- JWPCGLHIVLLRAW-UHFFFAOYSA-N benzhydryl-bis[5-(4-tert-butylpyridin-2-yl)-3-(trifluoromethyl)-1,2,4-triazol-1-yl]phosphane ruthenium(2+) Chemical compound FC(C1=NN(C(=N1)C1=NC=CC(=C1)C(C)(C)C)P(C(C1=CC=CC=C1)C1=CC=CC=C1)N1N=C(N=C1C1=NC=CC(=C1)C(C)(C)C)C(F)(F)F)(F)F.[Ru+2] JWPCGLHIVLLRAW-UHFFFAOYSA-N 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
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- 229910052793 cadmium Inorganic materials 0.000 description 1
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- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-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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- BLFVVZKSHYCRDR-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-2-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-2-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 BLFVVZKSHYCRDR-UHFFFAOYSA-N 0.000 description 1
- QQWXQKMVASVXCI-UHFFFAOYSA-N n-ethyl-n,2-dimethylpropan-1-amine Chemical compound CCN(C)CC(C)C QQWXQKMVASVXCI-UHFFFAOYSA-N 0.000 description 1
- 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
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
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- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
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- 239000012044 organic layer Substances 0.000 description 1
- 150000002923 oximes Chemical class 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
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001681 protective effect Effects 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
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
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- 125000003003 spiro group Chemical group 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- FVRNDBHWWSPNOM-UHFFFAOYSA-L strontium fluoride Chemical compound [F-].[F-].[Sr+2] FVRNDBHWWSPNOM-UHFFFAOYSA-L 0.000 description 1
- 229910001637 strontium fluoride Inorganic materials 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 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
- 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
- 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
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
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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
- H10K85/631—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
- 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
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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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- 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
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- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
提供即使在膜厚為厚之情況,仍顯示高電荷輸送性,適用於有機EL元件的電洞注入層時可實現優異特性之電荷輸送性膜之製造方法及該電荷輸送性膜。
具有50nm~300nm之範圍內的膜厚之電荷輸送性膜之製造方法,具備將含有僅由N,N’-二芳基聯苯胺衍生物所構成的電荷輸送性物質、與摻雜劑物質、與有機溶劑之電荷輸送性膜形成用塗漆塗佈於基材上之步驟、與使得到的塗膜以下述式(S1)所表示之燒成溫度進行燒成之步驟。
燒成溫度>[232.5℃+(前述膜厚/20nm)×5℃] (S1)
Description
本發明係關於電荷輸送性膜之製造方法及電荷輸送性膜以及電荷輸送性膜之電荷輸送性提升方法。
有機電致發光(以下,稱有機EL)元件中,作為發光層或電荷注入層,使用由有機化合物所構成的電荷輸送性膜。尤其電洞注入層負責陽極與電洞輸送層或者發光層之電荷授受,為了達成有機EL元件的低電壓驅動及高亮度,執行重要的功能。
電洞注入層之形成方法,大抵分為以蒸鍍法為代表的乾製程與以旋轉塗佈法為代表的濕製程,比較此等各製程,濕製程可大面積有效率地製造平坦性高的薄膜。因此在有機EL顯示器大面積化不斷進展的現在,期望可以濕製程形成之電洞注入層。
有鑑於如此,本發明者們開發了能得到可適用各種濕製程,同時適用於有機EL元件的電洞注入層的
場合,可實現優異的EL元件特性之薄膜之電荷輸送性材料或對用於其之有機溶劑溶解性良好的化合物(例如專利文獻1~4作為參考))。
但是關於電洞注入層用之溼製程材料常被要求改善,尤其追求可得到電荷輸送性優異的薄膜之溼製程材料。
[專利文獻1]國際公開第2008/032616號
[專利文獻2]國際公開第2008/129947號
[專利文獻3]國際公開第2006/025342號
[專利文獻4]國際公開第2010/058777號
[專利文獻5]日本特開2009-64696號
然而,有機EL元件的構造大致可分為底部發光構造與頂部發光構造。在底部發光構造之元件,基板側使用透明陽極,由基板側取出光,而在頂部發光構造之元件,使用由金屬所構成的反射陽極,由與基板相反方向之透明電極(陰極)側取出光。
因為頂部發光構造之元件,並非如底部發光構造之元件般為由基板側取出光者,沒有來自發光層之光被TFT遮斷之問題,因此,在頂部發光構造之元件,有可維持高
開口率之優點。結果,由可提高光取出效率、可實現元件的低電耗化或長壽命化,近年頂部發光構造之元件受到注目。
關於如此之頂部發光構造之元件,已知從發光層的發光面到反射陽極為止的光學距離符合指定條件時,藉由干涉效果可實現光取出效率的提升(例如專利文獻5作為參考)。因此,以藉由干涉效果提升光取出效率為目的,進行著嘗試設定從配合發光波長的發光面至反射陽極為止的光學距離,追求具有可確保能實現最適合條件之充分長度的光學距離用之厚度的電洞注入層等之電荷輸送性膜。
本發明為有鑑於上述情形而成者,以提供即使在膜厚為厚之情況,仍顯示高電荷輸送性,適用於有機EL元件的電洞注入層時可實現優異特性之電荷輸送性膜之製造方法、電荷輸送性膜、有機電致發光元件、有機電致發光元件之製造方法、電荷輸送性膜之電荷輸送性提升方法為目的。
本發明者們努力檢討結果,發現藉由將含有僅由N,N’-二芳基聯苯胺衍生物所構成的電荷輸送性物質、摻雜劑物質及有機溶劑之塗漆塗佈於基材上,將藉此而得到的塗膜在指定溫度以上進行燒成,能得到即使為厚膜的場合,電荷輸送性仍優異的電荷輸送性膜、及藉由將
該電荷輸送性膜用於有機EL元件,可實現優異亮度特性,而完成本發明。
即本發明之第1態樣為具有50nm~300nm之範圍內的膜厚之電荷輸送性膜之製造方法,其係以具備將含有僅由N,N’-二芳基聯苯胺衍生物所構成的電荷輸送性物質、與摻雜劑物質、與有機溶劑之電荷輸送性膜形成用塗漆塗佈於基材上之步驟、與將得到的塗膜以式(S1)所表示之燒成溫度進行燒成之步驟為特徵之電荷輸送性膜之製造方法。
燒成溫度>[232.5℃+(前述膜厚/20nm)×5℃] (S1)
本發明之第2態樣為前述燒成溫度以式(S2)表示之第1態樣記載之電荷輸送性膜之製造方法。
燒成溫度>[237.5℃+(前述膜厚/20nm)×5℃] (S2)
本發明之第3態樣為前述摻雜劑物質含有芳基磺酸化合物的第1或2態樣記載之電荷輸送性膜之製造方法。
本發明之第4態樣為前述摻雜劑物質含有雜多元酸的第1~3的任一態樣記載之電荷輸送性膜之製造方法。
本發明之第5態樣為前述N,N’-二芳基聯苯胺衍生物為N,N’-二苯基聯苯胺的第1~4之任一態樣記載之電荷輸送性膜之製造方法。
本發明之第6態樣為以第1~5的任一態樣記載之電荷輸送性膜之製造方法所製造為特徵之電荷輸送性
膜。
本發明之第7態樣為以具有第6態樣記載之電荷輸送性膜為特徵之有機電致發光元件。
本發明之第8態樣為前述電荷輸送性膜為電洞注入層、電洞輸送層或電洞注入輸送層的第7態樣記載之有機電致發光元件。
本發明之第9態樣為以包含第1~5的任一態樣記載之電荷輸送性膜之製造方法為特徵之有機電致發光元件之製造方法。
本發明之第10的態樣為由含有僅由N,N’-二芳基聯苯胺衍生物所構成的電荷輸送性物質、與摻雜劑物質、與有機溶劑之電荷輸送性膜形成用塗漆所得到之具有50nm~300nm之範圍內的膜厚之電荷輸送性膜之電荷輸送性提升方法,其為以具備將前述電荷輸送性膜形成用塗漆所得到之塗膜以式(S1)所表示之燒成溫度進行燒成之步驟為特徵之電荷輸送性膜之電荷輸送性提升方法。
燒成溫度>[232.5℃+(前述膜厚/20nm)×5℃] (S1)
本發明之第11態樣為前述燒成溫度以式(S2)表示之第10的態樣記載之電荷輸送性膜之電荷輸送性提升方法。
燒成溫度>[237.5℃+(前述膜厚/20nm)×5℃] (S2)
根據本發明之製造方法,可得到即使膜厚為
厚之場合,電荷輸送性仍優、用作為有機EL元件的電洞注入層時,可實現優異特性之膜。因此,藉由使用該製造方法所得到的膜作為電洞注入層,可以能維持著優異特性的方式確保頂部發光構造之有機EL元件中之從發光面至反射陽極為止的充分距離。由如此之理由,本發明之製造方法,可期待,例如以下之利用:可能引起導因於其元件內的機能性膜薄之干涉所導致的發光效率降低之問題之頂部發光型有機EL元件等,被要求膜的電荷輸送性及膜的厚度之裝置用電荷輸送性膜。
根據本發明之電荷輸送性膜之電荷輸送性提升方法,可有效提升厚膜的電荷輸送性膜的電荷輸送性。
進一步,本發明之該電荷輸送性膜,不僅電荷輸送性、均勻性亦優異,故亦可期待在電容器電極保護膜、防靜電膜、有機薄膜太陽電池的電洞捕集層(陽極緩衝層)等之應用。
以下,將本發明進而詳細說明。
在本發明之電荷輸送性膜之製造方法,使用含有僅由N,N’-二芳基聯苯胺衍生物所構成的電荷輸送性物質、與摻雜劑物質、與有機溶劑之電荷輸送性膜形成用塗漆。
N,N’-二芳基聯苯胺衍生物中之N位及N'位之芳基,可舉例如碳數6~20的芳基,具體例,可舉例如苯基、1-萘基、2-萘基、1-蒽基、2-蒽基、9-蒽基、1-菲
基、2-菲基、3-菲基、4-菲基、9-菲基等。
N,N’-二芳基聯苯胺衍生物中之N位之芳基及N'位之芳基,以相同基為佳。
N,N’-二芳基聯苯胺衍生物之具體例,可舉例如N,N’-二苯基聯苯胺、N,N’-二(1-萘基)聯苯胺、N,N’-二(2-萘基)聯苯胺、N-(1-萘基)-N’-(2-萘基)聯苯胺等,但不限於此等。
此等中,以N,N’-二苯基聯苯胺、N,N’-二(1-萘基)聯苯胺、N,N’-二(2-萘基)聯苯胺為佳,若考量得到的膜的透明性,以N,N’-二苯基聯苯胺為最佳。
摻雜劑物質方面,為溶於塗漆使用之至少一種的溶劑者則不特別限制,可使用無機系之摻雜劑物質、或有機系之摻雜劑物質任一。
尤其無機系之摻雜劑物質方面,以雜多元酸為佳。
雜多元酸係指作為代表之式(D1)所表示之Keggin型或者式(D2)所表示之Dawson型的化學構造所示之具有雜原子在分子中心位置之構造,且為釩(V)、鉬(Mo)、鎢(W)等之含氧酸之異多元酸與異種元素之含氧酸縮合而成的多元酸。如此之異種元素之含氧酸方面,主要可舉例如矽(Si)、磷(P)、砷(As)的含氧酸。
雜多元酸之具體例,可舉例如磷鉬酸、矽鉬酸、磷鎢酸、矽鎢酸、磷鎢鉬酸等,此等可單獨使用,亦可2種以上組合使用。又,本發明使用的雜多元酸可以市售品取得,又,亦可以習知方法合成。
尤其使用1種類的雜多元酸時,該1種類的雜多元酸以磷鎢酸或磷鉬酸為佳、磷鎢酸為最佳。又,使用2種類以上之雜多元酸時,該2種類以上之雜多元酸之1個以磷鎢酸或磷鉬酸為佳、磷鎢酸更佳。
又,雜多元酸為即使在元素分析等的定量分析中,比一般式所表示之構造之元素的數為多者或少者,只要其為以市售品取得者、或者依據習知合成方法適當合成者,則在本發明中皆可使用。
亦即,例如一般磷鎢酸以化學式H3(PW12O40).nH2O、磷鉬酸以化學式H3(PMo12O40).nH2O分別表示,但定量分析中,即使該式中之P(磷)、O(氧)或W(鎢)或者Mo(鉬)的數為多者或少者,只要其為以市售品取得者、或者依據習知合成方法適當合成者,則可在本發明中使用。此時,本發明所規定的雜多元酸之質量非合成物或市售品中純粹的磷鎢酸之質量(磷鎢酸含量),係指可作為市售品取得之形態及習知合成法可單離之形態中,含水合水或其他的雜質等的狀態之全質量。
另一方面,有機系之摻雜劑物質方面,尤以芳基磺酸為宜。其一例,可舉例如式(1)或(2)所表示之芳基磺酸。
式(1)中,A1為-O-或-S-,但以-O-為佳。A2為萘環或蒽環,以萘環為佳。A3為2~4價全氟聯苯基,j1為A1與A3之鍵數,且為符合2≦j1≦4之整數,但以A3為2價全氟聯苯基,且j1為2為佳。j2為鍵結於A2之磺酸基數,且符合1≦j2≦4之整數,但以2為宜。
式(2)中,A4~A8相互獨立,為氫原子、鹵素原子、氰基、碳數1~20的烷基、碳數1~20的鹵化烷基或碳數2~20的鹵化烯基,但A4~A8之中至少3個為鹵素原子。k為鍵結於萘環的磺酸基數,且為符合1≦k≦4的整數,但以2~4為佳、2更佳。
碳數1~20的鹵化烷基,可舉例如三氟甲基、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。碳數2~20的鹵化烯基,可舉例如全氟乙烯基、1-全氟丙烯基、全氟烯丙基、全氟丁烯基等。
鹵素原子、碳數1~20的烷基之例,可舉例與上述相同者,但鹵素原子方面,以氟原子為佳。
此等中,A4~A8為以氫原子、鹵素原子、氰基、碳數1~10的烷基、碳數1~10的鹵化烷基或碳數2~10的鹵化烯基,且A4~A8之中至少3個為氟原子為佳、以氫原子、氟原子、氰基、碳數1~5的烷基、碳數1~5的氟化烷基或碳數2~5的氟化烯基,且A4~A8之中至少3個為氟原子較佳、以氫原子、氟原子、氰基、碳數1~5的全氟烷基或碳數1~5的全氟烯基,且A4、A5及A8為氟原子又再佳。
又,全氟烷基係指烷基之氫原子全部被氟原子取代的基,全氟烯基係指烯基之氫原子全部被氟原子取代的基。
上述芳基磺酸之具體例如(b-1)~(b-6)所列舉,但不限於此等。
在本發明使用的電荷輸送性膜形成用塗漆,
以由該塗漆所得到之電荷輸送性膜的物性的調整等為目的,可含有三甲氧基矽烷、三乙氧基矽烷之烷氧基矽烷等之有機矽烷化合物等之其他的成分。
在本發明使用的電荷輸送性膜形成用塗漆含有的有機溶劑方面,可使用能良好溶解電荷輸送性物質及摻雜劑物質之良溶劑。
如此之良溶劑方面,例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N,N-二甲基丁醯胺、N,N-二乙基丁醯胺、N,N-甲基乙基丁醯胺、N,N-二甲基異丁醯胺、N,N-二乙基異丁醯胺、N-乙基-N-甲基異丁醯胺、N-甲基吡咯啶酮、1,3-二甲基-2-咪唑啉酮等之有機溶劑,但不限於此等。此等的溶劑可1種單獨或2種以上混合使用,其使用量相對於使用之溶劑全體,可為5~100質量%。
又,電荷輸送性物質、摻雜劑物質等皆以完全溶於上述溶劑為佳。
又,本發明中,以對基板之潤濕性的提升、溶劑的表面張力調整、極性的調整、沸點調整等之目的,除上述有機溶劑之外,可含有其他的有機溶劑。如此之其他的有機溶劑方面,以含二醇類、三醇類、烷二醇單烷基醚類、烷二醇二烷基醚類、二烷二醇單烷基醚類、二烷二醇二烷基醚類為佳,雖可舉例如二醇類、烷二醇單烷基醚類、二烷二醇單烷基醚類等,但不限於此等。此等的溶劑可1種單獨或2種以上混合使用,其使用量依共同使用的良溶劑的量而定。
其中,良溶劑以外的其他的有機溶劑方面,以二乙二醇、三乙二醇、二丙二醇、1,2-乙二醇、1,2-丙二醇、1,2-丁二醇、2,3-丁二醇、1,3-丁二醇、1,4-丁二醇、乙二醇單甲基醚、乙二醇單乙基醚、乙二醇丙基醚、乙二醇異丙基醚、乙二醇單丁基醚、乙二醇單異丁基醚、丙二醇單甲基醚、丙二醇單乙基醚、丙二醇單丙基醚、丙二醇單異丙基醚、丙二醇單丁基醚、丙二醇單異丁基醚、二乙二醇單甲基醚、二乙二醇單乙基醚、二乙二醇丙基醚、二乙二醇異丙基醚、二乙二醇單丁基醚、二乙二醇單異丁基醚、二丙二醇單甲基醚、二丙二醇單乙基醚、二丙二醇單丙基醚、二丙二醇單異丙基醚、二丙二醇單丁基醚、二丙二醇單異丁基醚為佳,以二乙二醇、三乙二醇、二丙二醇、1,2-乙二醇、1,2-丙二醇、1,2-丁二醇、2,3-丁二醇、1,3-丁二醇、1,4-丁二醇、乙二醇單甲基醚、丙二醇單甲基醚、二乙二醇單甲基醚、二丙二醇單甲基醚更佳。藉由考慮電荷輸送性物質或摻雜劑物質的種類或量的同時,且從如此之溶劑中選擇使用溶劑,可容易調製具有期望的液體物性之塗漆。
在本發明使用的電荷輸送性膜形成用塗漆之黏度,為因應製作之膜的厚度等或固形分濃度適宜設定者,通常在25℃為1~50mPa.s,其表面張力,通常為20~50mN/m。
在本發明使用的電荷輸送性膜形成用之固形分濃度為因應塗漆的黏度及表面張力等或製作之薄膜的厚
度等而適宜設定者,通常為0.1~20.0質量%程度,考量使塗漆的塗佈性提升,則較佳為0.5~10.0質量%程度、更佳為1.0~5.0質量%程度。又,在此所謂固形分係指在本發明使用的電荷輸送性膜形成用塗漆所含有的電荷輸送性物質及摻雜劑物質。
在本發明使用的電荷輸送性膜形成用塗漆中的摻雜劑物質的含量為考量電荷輸送性物質的種類或量等而適宜設定者,通常以質量比計,相對電荷輸送性物質1而言,為0.5~10程度。
尤其作為摻雜劑物質,含有雜多元酸時,雜多元酸之量以質量比計,相對電荷輸送性物質1而言,可為0.01~50程度,但較佳為0.1~10程度、更佳為1.0~5.0程度。又,作為摻雜劑物質,含有芳基磺酸時,芳基磺酸之量以莫耳比計,相對電荷輸送性物質1而言,可為0.1~10程度,但較佳為1.0~5.0程度。
電荷輸送性膜形成用塗漆的調製法方面,雖不特別限定,例如將電荷輸送性物質先溶於溶劑,於其中加入摻雜劑物質之手法或將電荷輸送性物質、摻雜劑物質的混合物溶於溶劑之手法。
又,例如有機溶劑有複數種時,可於良好溶解電荷輸送性物質及摻雜劑物質之溶劑中,首先將此等溶解,再於其中加入其他的溶劑,亦可於複數種的有機溶劑的混合溶劑中,依序溶解電荷輸送性物質及摻雜劑物質、或者同時溶解此等。
本發明中,電荷輸送性膜形成用塗漆,由再現性佳地得到高平坦性膜之觀點,以將電荷輸送性物質、摻雜劑物質等溶於有機溶劑後,使用亞微米等級之過濾器等過濾為佳。
又,在本發明使用的電荷輸送性膜形成用塗漆,同上述,為作為電荷輸送性物質,僅含有N,N’-二芳基聯苯胺衍生物者,換言之,在本發明使用的塗漆所含有的電荷輸送物質成分為僅由N,N’-二芳基聯苯胺衍生物所構成。如此,藉由僅使用N,N’-二芳基聯苯胺衍生物,可再現性佳地得到即使厚膜的場合,電荷輸送性仍優異的電荷輸送性膜。
本發明之製造方法,具備將上述說明之電荷輸送性膜形成用塗漆塗佈於基材上之步驟。又,基材係指塗佈有塗漆者,其具體例,可舉例如玻璃基板、ITO陽極、金屬陽極等,但不限於此等。
塗漆的塗佈方法方面,可舉例如浸漬法、旋轉塗佈法、轉印印刷法、輥塗法、毛刷塗佈、噴墨法、噴霧法、狹縫塗佈等,但不限於此等。塗佈方法,考量再現性佳地得到平坦性高的電荷輸送膜,以旋轉塗佈法、噴墨法、噴霧法為佳。又,以因應塗佈方法,調節塗漆的黏度及表面張力為佳。
本發明中,為了再現性佳地得到具有均勻成膜面及高電荷輸送性的厚膜的電荷輸送性膜,以將塗漆在大氣環境下燒成為佳。
本發明之製造方法,具備將上述步驟所得到的塗膜以下述式(S1)所表示之燒成溫度進行燒成之步驟。藉由採用如此之溫度,不管膜的厚度程度,可再現性佳地得到厚的電荷輸送性膜。
燒成溫度>[232.5℃+(膜厚/20nm)×5℃] (S1)
尤其將得到的電荷輸送性膜用作為有機EL元件的電洞注入層等之機能層時,考量再現性佳地得到耐久性優異的有機EL元件,在本發明中,以將塗膜以下述式(S2)所表示之燒成溫度燒成為佳。
燒成溫度>[237.5℃+(膜厚/20nm)×5℃] (S2)
又,燒成時,滿足上述溫度條件下,以表現更高均勻成膜性、在基材上進行反應之目的,可設定2階段以上之溫度變化。加熱可使用例如加熱板或烤箱等適當的機器進行。
又,以上述式所示之燒成溫度進行燒成前,可以較上述式所示之燒成溫度低的溫度,主要以溶劑的除去等為目的,進行乾燥(預燒成)。
具備以上說明的步驟的本發明之電荷輸送性膜之製造方法,尤其適合於具有50nm~300nm之範圍內的膜厚之電荷輸送性膜之製造。根據本發明之製造方法,可再現性佳地得到即使為如此之厚度,平坦性與電荷輸送性仍優、用作為有機EL元件的電洞注入層時,能實現優異的亮度特性之膜。
例如厚度為50nm時,需要比245℃高、較佳
為比250℃更高之燒成溫度,為300nm時,需要比307.5℃更高、較佳為比312.5℃更高之燒成溫度。
尤其由比以上述式所示之燒成溫度更低溫度燒成之場合,再現性更佳地得到電荷輸送性優異的膜之觀點,膜厚的下限值,較佳為70nm以上、更佳為75nm以上、再佳為90nm以上、又再佳為95nm以上,上限值較佳為250nm、更佳為200nm、再佳為175nm、又更佳為150nm、再更佳為130nm。
本發明之電荷輸送性膜,在有機EL元件中,可適用作為電洞注入層,但亦可用作為電洞注入輸送層等之電荷輸送性機能層。
本發明之有機EL元件,為具有一對電極,且於此等電極間具有前述本發明之電荷輸送性膜者。
有機EL元件的代表構成方面,可舉例如下述(a)~(f),但不限於此等。又,下述構成中,因應必要,亦可於發光層與陽極間設置電子阻隔層等、於發光層與陰極間設置正孔(電洞)阻隔層等。又,電洞注入層、電洞輸送層或者電洞注入輸送層亦可兼備作為電子阻隔層等之機能,電子注入層、電子輸送層或者電子注入輸送層亦可兼備作為正孔(電洞)阻隔層等之機能。
(a)陽極/電洞注入層/電洞輸送層/發光層/電子輸送層/電子注入層/陰極
(b)陽極/電洞注入層/電洞輸送層/發光層/電子注入輸送層/陰極
(c)陽極/電洞注入輸送層/發光層/電子輸送層/電子注入層/陰極
(d)陽極/電洞注入輸送層/發光層/電子注入輸送層/陰極
(e)陽極/電洞注入層/電洞輸送層/發光層/陰極
(f)陽極/電洞注入輸送層/發光層/陰極
「電洞注入層」、「電洞輸送層」及「電洞注入輸送層」係指發光層與陽極間所形成之層,為具有將電洞從陽極輸送至發光層之機能者。發光層與陽極間,電洞輸送性材料的層僅設置1層時,其為「電洞注入輸送層」,於發光層與陽極間,電洞輸送性材料的層設置2層以上時,靠近陽極之層為「電洞注入層」、其以外的層為「電洞輸送層」。尤其電洞注入層及電洞注入輸送層,使用不僅來自陽極的電洞受容性、對各自電洞輸送層及發光層的電洞注入性亦優異的膜。
「電子注入層」、「電子輸送層」及「電子注入輸送層」係指在發光層與陰極間所形成之層,為具有將電子由陰極輸送至發光層之機能者。在發光層與陰極間,電子輸送性材料的層僅設置1層時,其為「電子注入輸送層」、在發光層與陰極間,電子輸送性材料的層設置2層以上時,靠近陰極之層為「電子注入層」、其以外的層為「電子輸送層」。
「發光層」係指具有發光機能的有機層,採用摻雜系統時,含有主體材料與摻雜劑材料。此時,主體材料主要具有促成電子與電洞之再鍵結,使激發子封閉在
發光層內之機能,摻雜劑材料具有使再鍵結所得到的激發子有效率地發光之機能。磷光元件的場合,主體材料主要具有將摻雜劑所生成之激發子封閉於發光層內之機能。
製作具備本發明之電荷輸送性膜的有機EL元件時之使用材料或製作方法方面,可舉例如下述般者,但不限於此等。
使用的電極基板,以預先進行以洗劑、醇、純水等之液體洗淨淨化為佳,例如在陽極基板,以使用前進行UV臭氧處理、氧-電漿處理等之表面處理為佳。但,陽極材料以有機物為主成分時,可不進行表面處理。
本發明之電荷輸送性膜為電洞注入層時的本發明之有機EL元件之製作方法的一例,如下。
由前述方法,在陽極基板上塗佈電荷輸送性膜形成用塗漆後進行燒成,於電極上製作電洞注入層。於該電洞注入層上,依序設置電洞輸送層、發光層、電子輸送層、電子注入層、陰極。電洞輸送層、發光層、電子輸送層及電子注入層,因應使用的材料的特性等,以蒸鍍法或塗佈法(溼製程)的任一形成即可。
陽極材料方面,可舉例如以銦錫氧化物(ITO)、銦鋅氧化物(IZO)為代表的透明電極或由以鋁為代表的金屬或此等之合金等所構成的金屬陽極,以經平坦化處理者為佳。亦可使用具有高電荷輸送性的聚噻吩衍生物或聚苯胺衍生物。
又,構成金屬陽極的其他的金屬方面,可舉
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、鉍或此等之合金等,但不限於此等。
形成電洞輸送層之材料方面,可舉例如(三苯基胺)二聚物衍生物、[(三苯基胺)二聚物]螺二聚物、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-螺二芴、N,N'-雙(萘-1-基)-N,N'-雙(苯基)-9,9-螺二芴、N,N'-雙(3-甲基苯基)-N,N'-雙(苯基)-9,9-二甲基-芴、N,N'-雙(萘-1-基)-N,N'-雙(苯基)-9,9-二甲基-芴、N,N'-雙(3-甲基苯基)-N,N'-雙(苯基)-9,9-二苯基-芴、N,N'-雙(萘-1-基)-N,N'-雙(苯基)-9,9-二苯基-芴、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-螺二芴、9,9-雙[4-(N,N-雙-聯苯基-4-基-胺基)苯基]-9H-芴、9,9-雙[4-(N,N-雙-萘-2-基-胺基)苯基]-9H-芴、9,9-雙[4-(N-萘-1-基-N-苯基胺基)-苯基]-9H-芴、2,2',7,7'-肆[N-萘基(苯基)-胺基]-9,9-螺二芴、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-螺二芴、2,2'-雙(N,N-二苯基胺基)-9,9-螺二芴、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-螺二芴、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-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-萘基(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"-三噻吩(BMA-3T)等之寡噻吩類等之電洞輸送性低分子材料等。
形成發光層之材料方面,可舉例如參(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)-4-(p-苯基酚鹽)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)-芴-2-基]-9,9-二(4-甲基苯基)芴、2-甲基-9,10-雙(萘-2-基)蒽、2-(9,9-螺二芴-2-基)-9,9-螺二芴、2,7-雙(9,9-螺二芴-2-基)-9,9-螺二芴、2-[9,9-二(4-甲基苯基)-芴-2-基]-9,9-二(4-甲基苯基)芴、2,2'-二芘基-9,9-螺二芴、1,3,5-參(芘-1-基)苯、9,9-雙[4-(芘基)苯基]-9H-芴、2,2'-二(9,10-二苯基蒽)、2,7-二芘基-9,9-螺二芴、1,4-二(芘-1-基)苯、1,3-二(芘-1-基)苯、6,13-二(聯苯基-4-基)並五苯、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-4-基)-
9,9'-雙蒽、N,N'-二(萘-1-基)-N,N'-二苯基-[1,1':4',1":4",1'''-四聯苯]-4,4'''-二胺、4,4'-二[10-(萘-1-基)蒽-9-基]聯苯、二苯並{[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'-雙蒽-10-基)-9,9-二甲基-9H-芴-2-基)芘、1-(7-(9,9'-雙蒽-10-基)-9,9-二己基-9H-芴-2-基)芘、1,3-雙(咔唑-9-基)苯、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)-9,9-二甲基芴、2,2',7,7'-肆(咔唑-9-基)-9,9-螺二芴、2,7-雙(咔唑-9-基)-9,9-二(p-甲苯基)芴、9,9-雙[4-(咔唑-9-基)-苯基]芴、2,7-雙(咔唑-9-基)-9,9-螺二芴、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)-9,9-二辛基芴、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)-3,6-二三苯甲基-9H-咔唑、9-(4-t-丁基苯基)-3,6-雙(9-(4-甲氧基苯基)-9H-芴-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-芴-9-基)苯基)矽烷、9,9-二甲基-N,N-二苯基-7-(4-(1-苯基-1H-苯並[d]咪唑-2-基)苯基)-9H-芴-2-胺、3,5-雙(3-(9H-咔唑-9-基)苯基)吡啶、9,9-螺二芴-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-芴-9-基)-9-苯基-9H-咔唑、4,4,8,8,12,12-六(p-甲苯基)-4H-
8H-12H-12C-氮雜二苯並[cd,mn]芘、4,7-二(9H-咔唑-9-基)-1,10-菲繞啉、2,2'-雙(4-(咔唑-9-基)苯基)聯苯、2,8-雙(二苯基磷醯基)二苯並[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,形成發光層。
發光性摻雜劑方面,可舉例如3-(2-苯並噻唑基)-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-苯並噻唑基)喹嗪並[9,9a,1gh]香豆素、喹吖啶酮、N,N'-二甲基-喹吖啶酮、參(2-苯基吡啶)銥(III)(Ir(ppy)3)、雙(2-苯基吡啶)(乙醯丙酮酸)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-羥基苯基)苯並噻唑基]鋅(II)、N10,N10,N10,N10-四(p-甲苯基)-9,9'-雙蒽-10,10'-二胺、N10,N10,N10,N10-四苯基-9,9'-雙蒽-10,10'-二胺、N10,N10-二苯基-N10,N10-二萘基-9,9'-雙蒽-10,10'-二胺、4,4'-雙(9-乙基-3-咔唑伸乙烯基)-1,1'-聯苯、苝、2,5,8,11-四-t-丁基苝、1,4-雙[2-(3-N-乙基咔唑)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-吡啶基)苯基-(2-羧基吡啶基)]銥(III)、4,4'-雙
[4-(二苯基胺基)苯乙烯基]聯苯、雙(2,4-二氟苯基吡啶基)肆(1-吡唑基)硼酸鹽銥(III)、N,N'-雙(萘-2-基)-N,N'-雙(苯基)-參(9,9-二甲基亞芴)、2,7-雙{2-[苯基(m-甲苯基)胺基]-9,9-二甲基-芴-7-基}-9,9-二甲基-芴、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-苯基苯胺、fac-銥(III)參(1-苯基-3-甲基苯咪唑啉-2-叉-C,C2)、mer-銥(III)參(1-苯基-3-甲基苯咪唑啉-2-叉-C,C2)、2,7-雙[4-(二苯基胺基)苯乙烯基]-9,9-螺二芴、6-甲基-2-(4-(9-(4-(6-甲基苯並[d]噻唑-2-基)苯基)蒽-10-基)苯基)苯並[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(2,4-二氟苯基吡啶基)(5-(吡啶-2-基)-1H-四唑基)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑)((2,4-二氟苄基)二苯基亞膦酸酯)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑特)(苄基二苯基亞膦酸酯)銥(III)、雙(1-(2,4-二氟苄基)-3-甲基苯咪唑鎓)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑基)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑特)(4',6'-二氟苯基吡啶基)銥(III)、雙(4',6'-二氟苯基吡啶基)(3,5-雙(三氟甲基)-2-(2'-吡啶基)吡咯)銥(III)、雙(4',6'-二氟苯基吡啶基)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑基)銥(III)、(Z)-6-基-N-(6-基喹啉-2(1H)-叉)喹啉-2-胺-BF2、(E)-2-(2-(4-(二甲基胺基)苯乙烯基)-6-甲基-4H-吡喃-4-叉)丙二腈、4-(二氰基伸甲基)-2-甲基-6-久洛尼定基-9-烯基-4H-吡喃、4-(二氰基伸甲基)-2-甲基-6-
(1,1,7,7-四甲基久洛尼定基-9-烯基)-4H-吡喃、4-(二氰基伸甲基)-2-t-丁基-6-(1,1,7,7-四甲基久洛尼定-4-基-乙烯基)-4H-吡喃、參(二苯甲醯基甲烷)菲繞啉銪(III)、5,6,11,12-四苯基丁省、雙(2-苯並[b]噻吩-2-基-吡啶)(乙醯丙酮酸)銥(III)、參(1-苯基異喹啉)銥(III)、雙(1-苯基異喹啉)(乙醯丙酮酸)銥(III)、雙[1-(9,9-二甲基-9H-芴-2-基)-異喹啉](乙醯丙酮酸)銥(III)、雙[2-(9,9-二甲基-9H-芴-2-基)喹啉](乙醯丙酮酸)銥(III)、參[4,4'-二-t-丁基-(2,2')-二吡啶]釕(III).雙(六氟磷酸鹽)、參(2-苯基喹啉)銥(III)、雙(2-苯基喹啉)(乙醯丙酮酸)銥(III)、2,8-二-t-丁基-5,11-雙(4-t-丁基苯基)-6,12-二苯基四並苯、雙(2-苯基苯並噻唑基)(乙醯丙酮酸)銥(III)、5,10,15,20-四苯基四苯並卟啉鉑、鋨(II)雙(3-三氟甲基-5-(2-吡啶)-吡唑特)二甲基苯基膦、鋨(II)雙(3-(三氟甲基)-5-(4-t-丁基吡啶基)-1,2,4-三唑基)二苯基甲基膦、鋨(II)雙(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑)二甲基苯基膦、鋨(II)雙(3-(三氟甲基)-5-(4-t-丁基吡啶基)-1,2,4-三唑基)二甲基苯基膦、雙[2-(4-n-己基苯基)喹啉](乙醯丙酮酸)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)吡啶基)銥(III)、雙(2-(9,9-二乙基-芴-2-基)-1-苯基-1H-苯並[d]咪唑)(乙醯丙酮酸)銥(III)、雙(2-苯基吡啶)(3-(吡啶-2-基)-2H-色烯-2-歐尼)銥(III)、雙(2-苯基喹啉)(2,2,6,6-四甲基庚烷-3,5-二歐尼)銥(III)、雙(苯基異喹啉)(2,2,6,6-四甲基庚烷-3,5-二歐尼)銥(III)、銥(III)雙
(4-苯基噻吩並[3,2-c]吡啶基-N,C2)乙醯丙酮酸、(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-吡喃-4-叉)丙二腈、雙(3-三氟甲基-5-(1-異喹啉基)吡唑特)(甲基二苯基膦)釕、雙[(4-n-己基苯基)異喹啉](乙醯基丙酮)銥(III)、白金(II)八乙基卟啉、雙(2-甲基二苯並[f,h]喹喔啉)(乙醯基丙酮)銥(III)、三[(4-n-己基苯基)羥基喹啉]銥(III)等。
形成電子輸送層之材料方面,可舉例如8-羥基喹啉-鋰、2,2',2"-(1,3,5-苄基甲苯基)-三(1-苯基-1-H-苯並咪唑)、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-菲繞啉、4,7-二苯基-1,10-菲繞啉、雙(2-甲基-8-喹啉)-4-(苯基苯酚)鋁、1,3-雙[2-(2,2'-二吡啶-6-基)-1,3,4-噁二唑5-基]苯、6,6'-雙[5-(聯苯基-4-基)-1,3,4-噁二唑2-基]-2,2'-二吡啶、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-菲繞啉、2,7-雙[2-(2,2'-二吡啶-6-基)-1,3,4-噁二唑5-基]-9,9-二甲基芴、1,3-雙[2-(4-t-丁基苯基)-1,3,4-噁二唑5-基]苯、三(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]菲繞啉、2-(萘-2-基)-4,7-二苯基-1,10-菲繞啉、苯基-二芘基膦氧化物、3,3',5,5'-四[(m-吡啶基)-苯-3-基]聯苯、1,3,5-三[(3-吡啶基)-苯-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-羥基苯並[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。
形成電子注入層之材料方面,例如氧化鋰(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、鋰乙醯丙酮酸(Li(acac))、乙酸鋰、安息香酸鋰等。
陰極材料方面,例如鋁、鎂-銀合金、鋁-鋰合金、鋰、鈉、鉀、銫等。
又,本發明之電荷輸送性膜為電洞注入層時的本發明之有機EL元件之製作方法的其他例,如下。
前述EL元件製作方法中,藉由取代進行電洞輸送層、發光層、電子輸送層、電子注入層的真空蒸鍍操作,依序形成電洞輸送層、發光層,可製作具有本發明之電荷輸送性膜之有機EL元件。具體上於陽極基板上塗佈電荷輸送性膜形成用塗漆,以前述方法,製作電洞注入層,於其上,依序形成電洞輸送層、發光層,進而蒸鍍陰極電極作成有機EL元件。
使用之陰極及陽極材料方面,可使用與前述相同者,可進行同樣的洗淨處理、表面處理。
電洞輸送層及發光層的形成方法方面,可舉例如於電洞輸送性高分子材料或者發光性高分子材料、或此等中加入有摻雜劑之材料,添加溶劑進行溶解、或均勻分散,各自塗佈於電洞注入層或電洞輸送層上後,進行燒成而成膜之方法。
電洞輸送性高分子材料方面,可舉例如聚[(9,9-二己基芴基-2,7-二基)-co-(N,N'-雙{p-丁基苯基}-1,4-二胺基伸苯基)]、聚[(9,9-二辛基芴基-2,7-二基)-co-(N,N'-雙{p-丁基苯基}-1,1'-伸二苯基-4,4-二胺)]、聚[(9,9-雙{1'-戊烯-5'-基}芴基-2,7-二基)-co-(N,N'-雙{p-丁基苯基}-1,4-二胺基伸苯基)]、聚[N,N'-雙(4-丁基苯基)-N,N'-雙(苯基)-聯苯胺]-以聚倍半矽氧烷封端、聚[(9,9-二辛基芴基-2,7-二基)-co-(4,4'-(N-(p-丁基苯基))二苯基胺)]等。
發光性高分子材料方面,可舉例如聚(9,9-二烷基芴)(PDAF)等的聚芴衍生物、聚(2-甲氧基-5-(2'-乙基己氧基)-1,4-伸苯基伸乙烯基)(MEH-PPV)等的聚伸苯基伸乙烯基衍生物、聚(3-烷基噻吩)(PAT)等的聚噻吩衍生物、聚乙烯基咔唑(PVCz)等。
溶劑方面,可舉例如甲苯、二甲苯、氯仿等,作為溶解或均勻分散法,可舉例如攪拌、加熱攪拌、超音波分散等的方法。
塗佈方法方面,非特別限定者,可舉例如噴墨法、噴霧法、浸漬法、旋轉塗佈法、轉印印刷法、輥塗法、刷毛塗佈等。又,塗佈以在氮、氬等的惰性氣體下進行為佳。
燒成方法方面,可舉例如惰性氣體下或真空中,以烤箱或加熱板進行加熱之方法。
本發明之電荷輸送性膜為電洞注入輸送層時的本發明之有機EL元件之製作方法的一例,如下。
於陽極基板上形成電洞注入輸送層,於該電洞注入輸送層上,依序設置發光層、電子輸送層、電子注入層、陰極。發光層、電子輸送層及電子注入層的形成方法及具體例可舉如同前述者。
陽極材料、形成發光層、發光性摻雜劑、電子輸送層及電子阻隔層之材料、陰極材料方面,可舉如同前述者。
又,電極及前述各層間之任意之間,因應必要可設置正孔阻隔層、電子阻隔層等。例如形成電子阻隔層之材料方面,例如參(苯基吡唑)銥等。
構成陽極與陰極及於此等間所形成之層之材料,因是否製造具備底部發光構造、頂部發光構造之任一的元件而異,故考量該點,選擇適宜材料。
通常在底部發光構造之元件,基板側使用透明陽極,由基板側取出光,而在頂部發光構造之元件,使用由金屬所構成的反射陽極,由位於基板相反方向之透明電極(陰極)側取出光。因此,例如陽極材料,分別係製造底部發光構造之元件時使用ITO等之透明陽極,製造頂部發光構造之元件時使用Al/Nd等之反射陽極。
本發明之有機EL元件,為了防止特性惡化,依據標準方法,因應必要可與捕水劑等同時密封。
以下,舉實施例將本發明更具體地說明,但本發明不限於下述實施例。又,使用裝置如下。
(1)基板洗淨:長州產業(股)製 基板洗淨裝置(減壓電漿方式)
(2)塗漆的塗佈:Mikasa(股)製 旋轉塗佈機MS-A100
(3)膜厚測定:(股)小坂研究所製 微細形狀測定機SurfcorderET-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元件的亮度等之測定:(有)Tech world製 I-V-L測定系統
(6)EL元件的壽命測定(半衰期的測定):(股)EHC製 有機EL亮度壽命評估系統PEL-105S
將N,N'-二苯基聯苯胺0.851g、與式(b-1)所表示之芳基磺酸化合物1.191g、與磷鎢酸(關東化學(股)製)0.511g溶於N,N’-二甲基咪唑啉酮20g。於得到的溶液中,加入三乙二醇單甲基醚12g、與己二醇8g,進行攪拌,得到塗漆。又,該芳基磺酸係依據國際公開第2006/025342號進行合成。
將調製例1所得到的塗漆塗佈於ITO基板上後,在120℃進行1分鐘乾燥,進一步,在255℃進行15分鐘燒成,於ITO基板上形成厚度80nm之均勻膜。ITO基板方面,使用銦錫氧化物(ITO)在表面上以膜厚150nm圖型化的25mm×25mm×0.7t之玻璃基板,使用前以O2電漿洗淨裝置(150W、30秒鐘)除去表面上之雜質。
接著,對形成膜的ITO基板,使用蒸鍍裝置(真空度1.0×10-5Pa),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,得到有機EL元件。此時,蒸鍍速度,以α-NPD、Alq3及鋁為0.2nm/秒、氟化鋰為0.02nm/秒之條件各自進行,膜厚各自為30nm、40nm、0.5nm及100nm。
又,為了防止空氣中的氧、水等之影響所致之特性劣化,EL元件在以密封基板密封後,評估其特性。密封用以下的程序進行。
在氧濃度2ppm以下,露點-85℃以下的氮環境中,將EL元件收納於密封基板間,將密封基板以接著材
((股)MORESCO製Moresco Moisture Cut WB90US(P))貼合。此時,將捕水劑(dynic(股)製HD-071010W-40)與EL元件一起收納於密封基板內。對經貼合的密封基板,照射UV光(波長365nm、照射量6,000mJ/cm2)後,在80℃進行1小時退火處理,使接著材硬化。
除使燒成溫度各自為260℃、265℃、270℃以外,與樣本1-1同樣方法,得到元件。
除使於ITO基板上形成之膜的厚度為100nm以外,與樣本1-1同樣方法,得到元件。
除使燒成溫度各自為260℃、265℃、270℃以外,與比較樣本1同樣方法,得到元件。
除使燒成溫度為260℃,ITO基板上形成之膜的厚度為120nm以外,與樣本1-1同樣方法,得到元件。
除使燒成溫度各自為265℃、270℃以外,與比較樣
本2同樣方法,得到元件。
測定使得到的元件以5V驅動時的亮度。結果如表1所示。測定得到的元件的亮度半衰期(初期亮度:5000cd/m2)。結果如表2所示。
如表1所示,在將本發明使用的上述說明之電荷輸送性膜形成用塗漆以符合燒成溫度>[232.5℃+(前述膜厚/20nm)×5℃]之式的燒成溫度進行燒成時,可得到亮
度特性優異的元件。即在燒成溫度為255℃時,電洞注入層的厚度為80nm時,初期亮度特性優異,但在厚度為100nm時,初期亮度特性差。又,在燒成溫度為260℃時,厚度為80nm及100nm時,初期亮度特性優異,但在厚度為120nm時,初期亮度特性差。進一步,在燒成溫度為265℃時,厚度為80nm及100nm時,初期亮度特性優,且厚度為120nm時,亮度特性亦良好。又,在燒成溫度為270℃時,厚度為80nm、100nm及120nm之任一膜厚時,皆亮度特性優異。
其中,如表2所示,尤其在符合燒成溫度>[237.5℃+(前述膜厚/20nm)×5℃]之式的燒成溫度進行燒成時,可得到亮度壽命亦優異之元件。即在燒成溫度為260℃、厚度為80nm時,燒成溫度為265℃、厚度為80nm及100nm時,以及燒成溫度為270℃厚度為80nm、100nm及120nm時,可得到初期亮度特性與亮度壽命優異的元件,但在燒成溫度為255℃、厚度為80nm時,燒成溫度為260℃、厚度為100nm時,以及燒成溫度為265℃、厚度為120nm時,如上述只能得到初期亮度特性雖優,但亮度壽命差之元件。
Claims (11)
- 一種電荷輸送性膜之製造方法,其係具有50nm~300nm之範圍內的膜厚之電荷輸送性膜之製造方法,其特徵為具備將含有僅由N,N’-二芳基聯苯胺衍生物所構成的電荷輸送性物質、與摻雜劑物質、與有機溶劑之電荷輸送性膜形成用塗漆塗佈於基材上之步驟、與將得到的塗膜以式(S1)所表示之燒成溫度進行燒成之步驟,燒成溫度>[232.5℃+(前述膜厚/20nm)×5℃] (S1)。
- 如請求項1記載之電荷輸送性膜之製造方法,其中,前述燒成溫度以式(S2)表示,燒成溫度>[237.5℃+(前述膜厚/20nm)×5℃] (S2)。
- 如請求項1記載之電荷輸送性膜之製造方法,其中,前述摻雜劑物質含有芳基磺酸化合物。
- 如請求項1記載之電荷輸送性膜之製造方法,其中,前述摻雜劑物質含有雜多元酸。
- 如請求項1記載之電荷輸送性膜之製造方法,其中,前述N,N’-二芳基聯苯胺衍生物為N,N’-二苯基聯苯胺。
- 一種電荷輸送性膜,其特徵為以請求項1~5中任1項記載之電荷輸送性膜之製造方法所製造。
- 一種有機電致發光元件,其特徵為具有請求項6 記載之電荷輸送性膜。
- 如請求項7記載之有機電致發光元件,其中,前述電荷輸送性膜為電洞注入層、電洞輸送層或電洞注入輸送層。
- 一種有機電致發光元件之製造方法,其特徵係含有請求項1~5中任1項記載之電荷輸送性膜之製造方法。
- 一種電荷輸送性膜之電荷輸送性提升方法,其係由含有僅由N,N’-二芳基聯苯胺衍生物所構成的電荷輸送性物質、與摻雜劑物質、與有機溶劑之電荷輸送性膜形成用塗漆所得到之具有50nm~300nm之範圍內的膜厚之電荷輸送性膜之電荷輸送性提升方法,其特徵為具備將由前述電荷輸送性膜形成用塗漆所得到之塗膜以式(S1)所表示之燒成溫度進行燒成之步驟,燒成溫度>[232.5℃+(前述膜厚/20nm)×5℃] (S1)。
- 如請求項10記載之電荷輸送性膜之電荷輸送性提升方法,其中,前述燒成溫度以式(S2)表示,燒成溫度>[237.5℃+(前述膜厚/20nm)×5℃] (S2)。
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