TW201726828A - 電荷輸送性塗料以及有機電致發光元件 - Google Patents
電荷輸送性塗料以及有機電致發光元件 Download PDFInfo
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- TW201726828A TW201726828A TW105116456A TW105116456A TW201726828A TW 201726828 A TW201726828 A TW 201726828A TW 105116456 A TW105116456 A TW 105116456A TW 105116456 A TW105116456 A TW 105116456A TW 201726828 A TW201726828 A TW 201726828A
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- 150000002894 organic compounds Chemical class 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
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical group OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 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
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000011698 potassium fluoride Chemical class 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 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
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000003003 spiro group Chemical group 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
- IKACLGBUTCDQFA-UHFFFAOYSA-N sulfane;toluene;hydrochloride Chemical compound S.Cl.CC1=CC=CC=C1 IKACLGBUTCDQFA-UHFFFAOYSA-N 0.000 description 1
- OCKIJXFPIAVYSS-UHFFFAOYSA-N sulfanium;benzene;chloride Chemical compound [SH3+].[Cl-].C1=CC=CC=C1 OCKIJXFPIAVYSS-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229950009390 symclosene Drugs 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
- SFLXUZPXEWWQNH-UHFFFAOYSA-K tetrabutylazanium;tribromide Chemical compound [Br-].[Br-].[Br-].CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC SFLXUZPXEWWQNH-UHFFFAOYSA-K 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000004360 trifluorophenyl group Chemical group 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- PRXNKYBFWAWBNZ-UHFFFAOYSA-N trimethylphenylammonium tribromide Chemical compound Br[Br-]Br.C[N+](C)(C)C1=CC=CC=C1 PRXNKYBFWAWBNZ-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- PSZXPGFNGPBEFR-UHFFFAOYSA-N trisodium butan-1-olate Chemical compound [Na+].[Na+].[Na+].CCCC[O-].CCCC[O-].CCCC[O-] PSZXPGFNGPBEFR-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 150000003672 ureas Chemical class 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
- 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
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Abstract
本發明提供含有由以下述式(1)表示之寡聚苯胺衍生物所成之電荷輸送物質、不含氟原子之電荷輸送性物質、及有機溶劑之電荷輸送性塗料以及含有由該塗料所得之薄膜之有機EL元件:□(式中,R1表示氫原子或可經取代之烷基,R2~R10分別獨立表示氫原子、鹵原子、硝基、氰基、或可經取代之烷基、烯基、炔基、芳基或雜芳基,A表示特定之含氟取代基,k表示1~20之整數)。
Description
本發明係有關電荷輸送性塗料以及有機電致發光(EL)元件。
有機EL元件中,作為發光層或電荷注入層,係使用由有機化合物所成之電荷輸送性薄膜。尤其,電洞注入層負責陽極與電洞輸送層或發光層間之電荷授受,發揮用以達成有機EL元件之低電壓驅動及高亮度之重要功能。
電洞注入層之形成方法,大致分為以蒸鍍法為代表之乾式製程及以旋塗為代表之濕式製程。若比較該等各製程,則濕式製程可有效地製造大面積且平坦性高的薄膜。因此,於已進展有機EL顯示器之大面積化之現在,期望能以濕式製程形成之電洞注入層。
鑑於此等情況,本發明人等開發出可應用於各種濕式製程、並且可獲得應用於有機EL元件之電洞注入層時可實現優異特性之薄膜之電荷輸送性材料,或對於其所使用之有機溶劑之溶解性良好之化合物及電荷輸送性
塗料(例如參考專利文獻1~4)。
[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
本發明之目的,與迄今已開發之前述專利文獻之技術同樣,在於提供可獲得應用於有機EL元件之電洞注入層時可實現優異特性之薄膜之電荷輸送性塗料,及包含由該塗料所得之薄膜之有機EL元件。
本發明人等為達成前述目的而重複積極檢討之結果,發現由含有特定氟原子之寡聚苯胺衍生物所成之電荷輸送物質、不含氟原子之電荷輸送性物質、有機溶劑、及根據必要之摻雜劑之電荷輸送性塗料所得之薄膜具有高的電荷輸送性,將該薄膜應用於有機EL元件之電洞注入層時,可實現優異電特性,因而完成本發明。
亦即,本發明提供下述電荷輸送性塗料及有
機EL元件。
1. 一種電荷輸送性塗料,其特徵係含有由以下述式(1)表示之含氟原子之寡聚苯胺衍生物所成之電荷輸送物質、不含氟原子之電荷輸送性物質、及有機溶劑,
(式中,R1表示氫原子或可經Z取代之碳數1~20之烷基,Z表示鹵原子、硝基、氰基、醛基、羥基、硫醇基、磺酸基、羧基、可經Z’取代之碳數6~20之芳基或可經Z’取代之碳數2~20之雜芳基,Z’表示鹵原子、硝基、氰基、醛基、羥基、硫醇基、磺酸基、或羧基;R2~R10分別獨立表示氫原子、鹵原子、硝基、氰基、或可經鹵原子取代之碳數1~20之烷基、碳數2~20之烯基、碳數2~20之炔基、碳數6~20之芳基或碳數2~20之雜芳基;A表示可經氰基、氯原子、溴原子、碘原子、硝基或碳數1~20之氟烷氧基取代之碳數1~20之氟烷基、碳數3~20之氟環烷基、碳數4~20之氟雙環烷基、碳數2~20之氟烯基或碳數2~20之氟炔基,可經氰基、氯原子、溴原子、碘原子、硝基、碳數
1~20之烷基、碳數1~20之氟烷基或碳數1~20之氟烷氧基取代之碳數6~20之氟芳基,可經碳數1~20之氟烷基、碳數3~20之氟環烷基、碳數4~20之氟雙環烷基、碳數2~20之氟烯基或碳數2~20之氟炔基取代並且可經氰基、鹵原子或碳數1~20之氟烷氧基取代之碳數6~20之芳基,可經氰基、氯原子、溴原子、碘原子、硝基、碳數1~20之氟烷氧基、碳數1~20之氟烷基、碳數3~20之氟環烷基、碳數4~20之氟雙環烷基、碳數2~20之氟烯基或碳數2~20之氟炔基取代之碳數7~20之氟芳烷基,或可經碳數1~20之氟烷基、碳數3~20之氟環烷基、碳數4~20之氟雙環烷基、碳數2~20之氟烯基或碳數2~20之氟炔基取代並且可經氰基、鹵原子或碳數1~20之氟烷氧基取代之碳數7~20之芳烷基,k表示1~20之整數)。
2. 如1之電荷輸送性塗料,其中A係可經氰基、氯原子、溴原子、碘原子、硝基或碳數1~20之氟烷氧基取代之碳數1~20之氟烷基,可經氰基、氯原子、溴原子、碘原子、硝基、碳數1~20之烷基、碳數1~20之氟烷基或碳數1~20之氟烷氧基取代之碳數6~20之氟芳基,或可經碳數1~20之氟烷基、碳數3~20之氟環烷基、碳數4~20之氟雙環烷基、碳數2~20之氟烯基或碳數2~20之氟炔基取代並且可經氰基、鹵原子或碳數1~20之氟烷氧基取代之碳數6~20之芳基。
3. 如2之電荷輸送性塗料,其中A係可經氰基、氯原子、溴原子、碘原子、硝基、碳數1~20之烷基、碳數1~20之氟烷基或碳數1~20之氟烷氧基取代之經3個以上氟原子取代之苯基,或可經碳數3~20之氟環烷基、碳數4~20之氟雙環烷基、碳數2~20之氟烯基或碳數2~20之氟炔基取代並且可經氰基、鹵原子或碳數1~20之氟烷氧基取代之苯基。
4. 如1~3中任一項之電荷輸送性塗料,其中R1為氫原子。
5. 如1~4中任一項之電荷輸送性塗料,其中R2~R10為氫原子。
6. 如1~5中任一項之電荷輸送性塗料,其中k為2~10之整數。
7. 如1~6中任一項之電荷輸送性塗料,其中前述不含氟原子之電荷輸送性物質係以下述式(4)表示者:
(式中,X1表示-NY1-、-O-、-S-、-(CR17R18)L-或單鍵,但m或n為0時,表示-NY1-;Y1分別獨立為氫原子、可經Z11取代之碳數1~20之烷基、碳數2~20之烯基或碳數2~20之炔基、或可經Z12
取代之碳數6~20之芳基或碳數2~20之雜芳基;R17及R18分別獨立表示氫原子、鹵原子、硝基、氰基、胺基、醛基、羥基、硫醇基、磺酸基、羧基、或可經Z11取代之碳數1~20之烷基、碳數2~20之烯基、或碳數2~20之炔基、可經Z12取代之碳數6~20之芳基或碳數2~20之雜芳基,或表示-NHY2、-NY3Y4、-C(O)Y5、-OY6、-SY7、-SO3Y8、-C(O)OY9、-OC(O)Y10、-C(O)NHY11或-C(O)NY12Y13基;R11~R16分別獨立表示氫原子、鹵原子、硝基、氰基、胺基、醛基、羥基、硫醇基、磺酸基、羧基、或可經Z11取代之碳數1~20之烷基、碳數2~20之烯基、或碳數2~20之炔基、可經Z12取代之碳數6~20之芳基或碳數2~20之雜芳基,或表示-NHY2、-NY3Y4、-C(O)Y5、-OY6、-SY7、-SO3Y8、-C(O)OY9、-OC(O)Y10、-C(O)NHY11或-C(O)NY12Y13基;Y2~Y13分別獨立表示可經Z11取代之碳數1~20之烷基、碳數2~20之烯基、或碳數2~20之炔基、或可經Z12取代之碳數6~20之芳基或碳數2~20之雜芳基;Z11表示鹵原子、硝基、氰基、胺基、醛基、羥基、硫醇基、磺酸基、羧基、或可經Z13取代之碳數6~20之芳基或碳數2~20之雜芳基;Z12表示鹵原子、硝基、氰基、胺基、醛基、羥基、硫醇基、磺酸基、羧基、或可經Z13取代之碳數1~20之烷基、碳數2~20之烯基或碳數2~20之炔基;
Z13表示鹵原子、硝基、氰基、胺基、醛基、羥基、硫醇基、磺酸基或羧基;m及n分別獨立表示0以上之整數,且滿足1≦m+n≦20)。
8. 如1~7中任一項之電荷輸送性塗料,其中進而含有摻雜劑。
9. 一種電荷輸送性薄膜,其係使用如1~8中任一項之電荷輸送性塗料製作者。
10. 一種有機電致發光元件,其具有如9之電荷輸送性薄膜。
11. 一種下述式(1)表示之含氟原子之寡聚苯胺衍生物之製造方法,其特徵為使式(2B)表示之胺化合物與以式(3B)或(3B’)表示之含氟原子之化合物在鹼存在下反應:
(式中,R1~R10、A及k與前述相同,X表示鹵原子,X’表示擬鹵原子;a表示0~19之整數,且滿足k>a)。
由本發明之電荷輸送性塗料製作之薄膜顯示非常高的電荷輸送性。因此,可較好地使用作為以有機EL原件為代表之電子裝置用薄膜。尤其藉由將該薄膜應用於有機EL元件之電洞注入層,可獲得亮度特性優異之有機EL元件。
又,本發明之電荷輸送性塗料由於即使以旋塗法或狹縫塗佈法等之可大面積成膜之各種濕式製程時,亦可再現性良好地製造電荷輸送性優異之薄膜,故亦可充分對應於近幾年之有機EL元件領域之進展。
本發明之電荷輸送性塗料含有由以下述式(1)表示之寡聚苯胺衍生物所成之電荷輸送物質。又,所謂電荷輸送性與導電性同義,亦與電洞輸送性同義。又,本發明之電荷輸送性塗料可為本身具有電荷輸送性,亦可於使用塗料所得之固體膜具有電荷輸送性。
式中,R1表示氫原子或可經Z取代之碳數1~20之烷基。Z表示鹵原子、硝基、氰基、醛基、羥基、硫醇基、磺酸基、羧基、可經Z’取代之碳數6~20之芳基或可經Z’取代之碳數2~20之雜芳基,Z’表示鹵原子、硝基、氰基、醛基、羥基、硫醇基、磺酸基、或羧基。
R2~R10分別獨立表示氫原子、鹵原子、硝基、氰基、或可經鹵原子取代之碳數1~20之烷基、碳數2~20之烯基、碳數2~20之炔基、碳數6~20之芳基或碳數2~20之雜芳基。
作為鹵原子舉例為氟原子、氯原子、溴原子、碘原子等。
碳數1~20之烷基可為直鏈狀、分支鏈狀、環狀之任一種,其具體例列舉為甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基、第三丁基、正戊基、正己基、正庚基、正辛基、正壬基、正癸基等碳數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、雙環癸基等碳數3~20之環狀烷基。
碳數2~20之烯基可為直鏈狀、分支鏈狀、環狀之任一種,其具體例列舉為乙烯基、正-1-丙烯基、正-2-丙烯基、1-甲基乙烯基、正-1-丁烯基、正-2-丁烯基、正-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、正-1-戊
烯基、正-1-癸烯基、正-1-二十碳烯基等。
碳數2~20之炔基可為直鏈狀、分支鏈狀、環狀之任一種,其具體例列舉為乙炔基、正-1-丙炔基、正-2-丙炔基、正-1-丁炔基、正-2-丁炔基、正-3-丁炔基、1-甲基-2-丙烯基、正-1-戊炔基、正-2-戊炔基、正-3-戊炔基、正-4-戊炔基、1-甲基-正-丁烯基、2-甲基-正-丁烯基、3-甲基-正-丁烯基、1,1-二甲基-正-丙烯基、正-1-己炔基、正-1-癸炔基、正-1-十五碳炔基、正-1-二十碳炔基等。
碳數6~20之芳基之具體例列舉為苯基、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。
碳數2~20之雜芳基之具體例列舉為2-噻吩基、3-噻吩基、2-呋喃基、3-呋喃基、2-噁唑基、4-噁唑基、5-噁唑基、3-異噁唑基、4-異噁唑基、5-異噁唑基、2-噻唑基、4-噻唑基、5-噻唑基、3-異噻唑基、4-異噻唑基、5-異噻唑基、2-咪唑基、4-咪唑基、2-吡啶基、3-吡啶基、4-吡啶基等。
該等中,作為R1,考慮寡聚苯胺衍生物對有機溶劑之溶解性時,較好為氫原子或可經Z取代之碳數1~10之烷基,更好為氫原子或可經Z取代之碳數1~4之烷基,最宜為氫原子。又,複數個R1各可相同亦可不同。
R1為氫原子時,與芳基磺酸、雜聚酸等之質
子酸等之摻雜劑一起使用時,可實現特別優異之電荷輸送性。
又,該等中,作為R2~R10,考慮寡聚苯胺衍生物對有機溶劑之溶解性時,較好為氫原子、鹵原子、硝基、氰基、或可經鹵原子取代之碳數1~10之烷基,更好為氫原子、鹵原子、或可經鹵原子取代之碳數1~4之烷基,考慮寡聚苯胺衍生物對有機溶劑之溶解性與電荷輸送性之平衡時,最宜為氫原子。又,複數個R2~R5各可相同亦可不同。
式(1)中,A表示:可經氰基、氯原子、溴原子、碘原子、硝基或碳數1~20之氟烷氧基取代之碳數1~20之氟烷基、碳數3~20之氟環烷基、碳數4~20之氟雙環烷基、碳數2~20之氟烯基或碳數2~20之氟炔基;可經氰基、氯原子、溴原子、碘原子、硝基、碳數1~20之烷基、碳數1~20之氟烷基或碳數1~20之氟烷氧基取代之碳數6~20之氟芳基;可經碳數1~20之氟烷基、碳數3~20之氟環烷基、碳數4~20之氟雙環烷基、碳數2~20之氟烯基或碳數2~20之氟炔基取代並且可經氰基、鹵原子或碳數1~20之氟烷氧基取代之碳數6~20之芳基;可經氰基、氯原子、溴原子、碘原子、硝基、碳數1~20之氟烷氧基、碳數1~20之氟烷基、碳數3~20之氟環烷基、碳數4~20之氟雙環烷基、碳數2~20之氟烯基或碳數2~20之氟炔基取代之碳數7~20之氟芳烷基;或可經碳數1~20之氟烷基、碳數3~20之氟環烷基、碳數4~20之氟雙環烷
基、碳數2~20之氟烯基或碳數2~20之氟炔基取代並且可經氰基、鹵原子或碳數1~20之氟烷氧基取代之碳數7~20之芳烷基。
前述氟烷基若為碳原子上之至少1個氫原子經氟原子取代之直鏈狀或分支鏈狀之烷基則未特別限定,舉例為例如氟甲基、二氟甲基、三氟甲基、1-氟乙基、2-氟乙基、1,2-二氟乙基、1,1-二氟乙基、2,2-二氟乙基、1,1,2-三氟乙基、1,2,2-三氟乙基、2,2,2-三氟乙基、1,1,2,2-四氟乙基、1,2,2,2-四氟乙基、1,1,2,2,2-五氟乙基、1-氟丙基、2-氟丙基、3-氟丙基、1,1-二氟丙基、1,2-二氟丙基、1,3-二氟丙基、2,2-二氟丙基、2,3-二氟丙基、3,3-二氟丙基、1,1,2-三氟丙基、1,1,3-三氟丙基、1,2,3-三氟丙基、1,3,3-三氟丙基、2,2,3-三氟丙基、2,3,3-三氟丙基、3,3,3-三氟丙基、1,1,2,2-四氟丙基、1,1,2,3-四氟丙基、1,2,2,3-四氟丙基、1,3,3,3-四氟丙基、2,2,3,3-四氟丙基、2,3,3,3-四氟丙基、1,1,2,2,3-五氟丙基、1,2,2,3,3-五氟丙基、1,1,3,3,3-五氟丙基、1,2,3,3,3-五氟丙基、2,2,3,3,3-五氟丙基、七氟丙基等。
前述氟環烷基若為碳原子上之至少1個氫原子經氟原子取代之環烷基則未特別限定,舉例為例如1-氟環丙基、2-氟環丙基、2,2-二氟環丙基、2,2,3,3-四氟環丙基、五氟環丙基、2,2-二氟環丁基、2,2,3,3-四氟環丁基、2,2,3,3,4,4-六氟環丁基、七氟環丁基、1-氟環戊基、3-氟環戊基、3,3-二氟環戊基、3,3,4,4-四氟環戊基、九氟環戊
基、1-氟環己基、2-氟環己基、4-氟環己基、4,4-二氟環己基、2,2,3,3-四氟環己基、2,3,4,5,6-五氟環己基、十一氟環己基等。
前述氟雙環烷基若為碳原子上之至少1個氫原子經氟原子取代之雙環烷基則未特別限定,舉例為例如3-氟雙環[1.1.0]丁-1-基、2,2,4,4-四氟雙環[1.1.0]丁-1-基、五氟雙環[1.1.0]丁-1-基、3-氟雙環[1.1.1]戊-1-基、2,2,4,4,5-五氟雙環[1.1.1]戊-1-基、2,2,4,4,5,5-六氟雙環[1.1.1]戊-1-基、5-氟雙環[3.1.0]己-6-基、6-氟雙環[3.1.0]己-6-基、6,6-二氟雙環[3.1.0]己-2-基、2,2,3,3,5,5,6,6-八氟雙環[2.2.0]己-1-基、1-氟雙環[2.2.1]庚-2-基、3-氟雙環[2.2.1]庚-2-基、4-氟雙環[2.2.1]庚-1-基、5-氟雙環[3.1.1]庚-1-基、1,3,3,4,5,5,6,6,7,7-十氟雙環[2.2.1]庚-2-基、十一氟雙環[2.2.1]庚-2-基、3-氟雙環[2.2.2]辛-1-基、4-氟雙環[2.2.2]辛-1-基等。
前述氟烯基若為碳原子上之至少1個氫原子經氟原子取代之烯基則未特別限定,舉例為例如1-氟乙烯基、2-氟乙烯基、1,2-二氟乙烯基、1,2,2-三氟乙烯基、2,3,3-三氟-1-丙烯基、3,3,3-三氟-1-丙烯基、2,3,3,3-四氟-1-丙烯基、五氟-1-丙烯基、1-氟-2-丙烯基、1,1-二氟-2-丙烯基、2,3-二氟-2-丙烯基、3,3-二氟-2-丙烯基、2,3,3-三氟-2-丙烯基、1,2,3,3-四氟-2-丙烯基、五氟-2-丙烯基等。
前述氟炔基若為碳原子上之至少1個氫原子經氟原子取代之炔基則未特別限定,舉例為例如氟乙炔
基、3-氟-1-丙炔基、3,3-二氟-1-丙炔基、3,3,3-三氟-1-丙炔基、1-氟-2-丙炔基、1,1-二氟-2-丙炔基等。
前述氟芳基若為碳原子上之至少1個氫原子經氟原子取代之芳基則未特別限定,舉例為例如2-氟苯基、3-氟苯基、4-氟苯基、2,3-二氟苯基、2,4-二氟苯基、2,5-二氟苯基、2,6-二氟苯基、3,4-二氟苯基、3,5-二氟苯基、2,3,4-三氟苯基、2,3,5-三氟苯基、2,3,6-三氟苯基、2,4,5-三氟苯基、2,4,6-三氟苯基、3,4,5-三氟苯基、2,3,4,5-四氟苯基、2,3,4,6-四氟苯基、2,3,5,6-四氟苯基、五氟苯基、2-氟-1-萘基、3-氟-1-萘基、4-氟-1-萘基、6-氟-1-萘基、7-氟-1-萘基、8-氟-1-萘基、4,5-二氟-1-萘基、5,7-二氟-1-萘基、5,8-二氟-1-萘基、5,6,7,8-四氟-1-萘基、七氟-1-萘基、1-氟-2-萘基、5-氟-2-萘基、6-氟-2-萘基、7-氟-2-萘基、5,7-二氟-2-萘基、七氟-2-萘基等。
作為氟芳基,考慮寡聚苯胺衍生物對有機溶劑之溶解性、寡聚苯胺衍生物之電荷輸送性、寡聚苯胺衍生物之原料獲得容易性等之平衡時,亦可經氰基、氯原子、溴原子、碘原子、硝基、碳數1~20之烷基、碳數1~20之氟烷基或碳數1~20之氟烷氧基取代,較好經3個以上之氟原子取代之苯基。
作為前述氟烷氧基,若為碳原子上之至少1個氫原子經氟原子取代之烷氧基則未特別限定,舉例為例如氟甲氧基、二氟甲氧基、三氟甲氧基、1-氟乙氧基、2-氟乙氧基、1,2-二氟乙氧基、1,1-二氟乙氧基、2,2-二氟乙
氧基、1,1,2-三氟乙氧基、1,2,2-三氟乙氧基、2,2,2-三氟乙氧基、1,1,2,2-四氟乙氧基、1,2,2,2-四氟乙氧基、1,1,2,2,2-五氟乙氧基、1-氟丙氧基、2-氟丙氧基、3-氟丙氧基、1,1-二氟丙氧基、1,2-二氟丙氧基、1,3-二氟丙氧基、2,2-二氟丙氧基、2,3-二氟丙氧基、3,3-二氟丙氧基、1,1,2-三氟丙氧基、1,1,3-三氟丙氧基、1,2,3-三氟丙氧基、1,3,3-三氟丙氧基、2,2,3-三氟丙氧基、2,3,3-三氟丙氧基、3,3,3-三氟丙氧基、1,1,2,2-四氟丙氧基、1,1,2,3-四氟丙氧基、1,2,2,3-四氟丙氧基、1,3,3,3-四氟丙氧基、2,2,3,3-四氟丙氧基、2,3,3,3-四氟丙氧基、1,1,2,2,3-五氟丙氧基、1,2,2,3,3-五氟丙氧基、1,1,3,3,3-五氟丙氧基、1,2,3,3,3-五氟丙氧基、2,2,3,3,3-五氟丙氧基、七氟丙基等。
作為前述可經碳數1~20之氟烷基、碳數3~20之氟環烷基、碳數4~20之氟雙環烷基、碳數2~20之氟烯基或碳數2~20之氟炔基取代並且可經氰基、鹵原子或碳數1~20之氟烷氧基取代之碳數6~20之芳基(以下方便起見,亦稱為經取代之芳基),若為碳原子上之至少1個氫原子經碳數1~20之氟烷基、碳數3~20之氟環烷基、碳數4~20之氟雙環烷基、碳數2~20之氟烯基或碳數2~20之氟炔基取代之芳基,則未特別限定,舉例為例如2-(三氟甲基)苯基、3-(三氟甲基)苯基、4-(三氟甲基)苯基、4-乙氧基-3-(三氟甲基)苯基、3-氟-4-三氟甲基苯基、4-氟-3-三氟甲基苯基、4-氟-2-三氟甲基苯基、2-氟-5-(三氟甲基)
苯基、3-氟-5-(三氟甲基)苯基、3,5-二(三氟甲基)苯基、2,4,6-三(三氟甲基)苯基、4-(五氟乙基)苯基、4-(3,3,3-三氟丙基)苯基、2,3,5,6-四氟-4-三氟甲基苯基、4-(全氟乙烯基)苯基、4-(全氟丙烯基)苯基、4-(全氟丁烯基)苯基等。
作為前述經取代之芳基,考慮寡聚苯胺衍生物對有機溶劑之溶解性、寡聚苯胺衍生物之電荷輸送性、寡聚苯胺衍生物之原料獲得容易性等之平衡時,較好為可經碳數3~20之氟環烷基、碳數4~20之氟雙環烷基、碳數2~20之氟烯基或碳數2~20之氟炔基取代並且可經氰基、鹵原子或碳數1~20之氟烷氧基取代之苯基(以下方便起見,亦稱為經取代之苯基),更好經1~3個三氟甲基取代之苯基,又更好為對-三氟甲基苯基。
作為前述氟芳烷基若為碳原子上之至少1個氫原子經氟原子取代之芳烷基則未特別限定,舉例為例如2-氟苄基、3-氟苄基、4-氟苄基、2,3-二氟苄基、2,4-二氟苄基、2,5-二氟苄基、2,6-二氟苄基、3,4-二氟苄基、3,5-二氟苄基、2,3,4-三氟苄基、2,3,5-三氟苄基、2,3,6-三氟苄基、2,4,5-三氟苄基、2,4,6-三氟苄基、2,3,4,5-四氟苄基、2,3,4,6-四氟苄基、2,3,5,6-四氟苄基、2,3,4,5,6-五氟苄基等。
作為前述可經碳數1~20之氟烷基、碳數3~20之氟環烷基、碳數4~20之氟雙環烷基、碳數2~20之氟烯基或碳數2~20之氟炔基取代並且可經氰基、鹵原子或碳數1~20之氟烷氧基取代之碳數7~20之芳烷基,若為碳原
子上之至少1個氫原子經碳數1~20之氟烷基、碳數3~20之氟環烷基、碳數4~20之氟雙環烷基、碳數2~20之氟烯基或碳數2~20之氟炔基取代之芳烷基,則未特別限定,舉例為例如2-三氟甲基苄基、3-三氟甲基苄基、4-三氟甲基苄基、2,4-二(三氟甲基)苄基、2,5-二(三氟甲基)苄基、2,6-二(三氟甲基)苄基、3,5-二(三氟甲基)苄基、2,4,6-三(三氟甲基)苄基等。
該等中,A更好為前述可經取代之碳數1~20之氟烷基、前述可經取代之碳數6~20之氟芳基或前述可經取代之芳基,更好為前述可經取代之碳數6~20之氟芳基或前述可經取代之芳基,又更好為前述可經取代之氟苯基或前述可經取代之苯基,再更好為前述可經取代之三氟苯基、前述可經取代之四氟苯基、前述可經取代之五氟苯基或經1~3個三氟甲基取代之苯基。
以下,列舉作為A之較佳基之具體例,但不限定於此。
且,式(1)中,k為1~20之整數,但基於寡聚苯胺衍生物對溶劑之溶解性之方面,較好為10以下,更好為8以下,又更好為5以下,再更好為4以下,且基於提高寡聚苯胺衍生物之電荷輸送性之方面,較好為2以上,更好為3以上,考慮溶解性與電荷輸送性之平衡時,最好為3。
前述含氟原子之寡聚苯胺衍生物可如下述反應流程圖A表示般,藉由使式(2A)表示之胺化合物與式(3A)表示之含氟原子之酸鹵化物反應而合成。此時,為了更有效率地進行反應,較好在鹼存在下進行反應。
(式中,R1~R10、A及k與前述相同,X表示氟原子、氯原子、溴原子、碘原子等之鹵原子,但較好為氯原子或
溴原子)。
式(2A)表示之胺化合物舉例為例如下述式表示者,但不限定於此。
作為式(3A)表示之含氟原子之酸鹵化物舉例為2-氟苯甲醯氯、3-氟苯甲醯氯、4-氟苯甲醯氯、2-氟-4-甲基苯甲醯氯、2-氟-5-甲基苯甲醯氯、3-氟-4-甲基苯甲醯氯、3-氟-6-甲基苯甲醯氯、4-氟-2-甲基苯甲醯氯、4-氟-3-甲基苯甲醯氯、2,3-二氟苯甲醯氯、2,4-二氟苯甲醯氯、2,5-二氟苯甲醯氯、2,6-二氟苯甲醯氯、3,4-二氟苯甲醯氯、3,5-二氟苯甲醯氯、3-氯-2-氟苯甲醯氯、4-氯-2-氟苯甲醯氯、5-氯-2-氟苯甲醯氯、2-氯-6-氟苯甲醯氯、2-氯-3-氟苯甲醯氯、2-氯-4-氟苯甲醯氯、2-氯-5-氟苯甲醯氯、3-氯-4-氟苯甲醯氯、3-氯-5-氟苯甲醯氯、3-溴-2-氟苯甲醯氯、4-溴-2-氟苯甲醯氯、5-溴-2-氟苯甲醯氯、2-溴-6-氟苯甲醯氯、2-溴-3-氟苯甲醯氯、2-溴-4-氟苯甲醯氯、2-溴-5-氟苯甲醯氯、3-溴-4-氟苯甲醯氯、3-溴-5-氟苯甲醯氯、2-氟-5-碘苯甲醯氯、2-氟-6-碘苯甲醯氯、2-氟
-3-(三氟甲基)苯甲醯氯、2-氟-5-(三氟甲基)苯甲醯氯、2-氟-6-(三氟甲基)苯甲醯氯、3-氟-4-(三氟甲基)苯甲醯氯、3-氟-5-(三氟甲基)苯甲醯氯、3-氟-6-(三氟甲基)苯甲醯氯、4-氟-2-(三氟甲基)苯甲醯氯、4-氟-3-(三氟甲基)苯甲醯氯、2-氟-4-硝基苯甲醯氯、2-氟-5-硝基苯甲醯氯、3-氟-2-硝基苯甲醯氯、3-氟-4-硝基苯甲醯氯、3-氟-6-硝基苯甲醯氯、4-氟-2-硝基苯甲醯氯、4-氟-3-硝基苯甲醯氯、4-氰基-2-氟苯甲醯氯、3-氰基-5-氟苯甲醯氯、2,3,4-三氟苯甲醯氯、2,3,5-三氟苯甲醯氯、2,3,6-三氟苯甲醯氯、2,4,5-三氟苯甲醯氯、2,4,6-三氟苯甲醯氯、3,4,5-三氟苯甲醯氯、4-氯-2,4-二氟苯甲醯氯、2,4-二氯-5-氟-4-硝基苯甲醯氯、2,4,5-三氟-3-甲基-6-硝基苯甲醯氯、2,3,4,5-四氟苯甲醯氯、2,3,5,6-四氟苯甲醯氯、2,3,5,6-四氟-4-甲基-苯甲醯氯、2,3,4,5-四氟-6-硝基苯甲醯氯、2,3,4,5,6-五氟苯甲醯氯、2-(三氟甲基)苯甲醯氯、3-(三氟甲基)苯甲醯氯、4-(三氟甲基)苯甲醯氯、3-三氟甲基-4-乙氧機苯甲醯氯、3,5-雙(三氟甲基)苯甲醯氯、2,4,6-三(三氟甲基)苯甲醯氯、4-(五氟乙基)苯甲醯氯、4-(3-四氟丙基)苯甲醯氯、2,3,5,6-四氟-4-(三氟甲基)苯甲醯氯、2,3,5,6-四氟-4-(三氟乙烯基)苯甲醯氯、2,3,5,6-四氟-4-(五氟烯丙基)苯甲醯氯等。
作為鹼舉例為第三丁氧化鈉(t-BuONa)、第三丁氧化鉀等之烷氧化物;氟化鋰、氟化鉀、氟化銫等之氟化物鹽類;碳酸鈉、碳酸鉀、碳酸氫鈉、碳酸氫鉀等之碳
酸鹽類;三甲胺、三乙胺、二異丙基乙胺、四甲基乙二胺、吡啶、嗎啉、N-甲基嗎啉、奎寧環、1,4-二氮雜雙環[2.2.2]辛烷、4-二甲胺基吡啶等之胺類,但若為該反應中所用者則未特別限定。尤其,基於處理容易,較好為三乙胺、吡啶、二異丙基乙胺等。
反應溶劑較好為非質子性極性有機溶劑,例如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-咪唑啶酮、二甲基亞碸、四氫呋喃、二噁烷等。基於反應後之反應溶劑之去除容易性觀點,較好為N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、四氫呋喃、二噁烷等。
反應溫度雖考慮所用原料化合物或觸媒種類或量,而自溶劑之熔點至沸點之範圍適當設定,但通常為0~200℃左右,較好為20~150℃。且反應時間由於根據所用原料化合物或觸媒種類或量、反應溫度等而異故無法一概而論,但通常為1~24小時左右。
反應結束後,依據常用方法進行後處理,可獲得成為目的之含氟原子之寡聚苯胺衍生物。
又,式(3A)表示之含氟原子之酸鹵化物可藉由使對應之含氟羧酸與例如亞硫醯氯或草醯氯、磷醯氯、硫醯氯、三氯化磷、五氯化磷等之親電子之鹵化劑反應而獲得。且,對應之含氟羧酸可使用市售品,亦可以習知方法(例如日本特開平9-67303號公報、日本特開平9-67304號公報、日本特開2002-284733號公報)合成。
前述含氟原子之寡聚苯胺衍生物亦可如下述反應流程圖B或C表示般,使式(2B)表示之胺化合物與式(3B)或(3B’)表示之含氟化合物在鹼存在下反應而合成。
(式中,R1~R10、A及k與前述相同,X表示鹵原子,X’表示擬鹵原子,a表示0~19之整數,且滿足k>a)。
作為鹵原子,舉例為與前述相同者,但較好
為溴原子、碘原子。作為擬鹵原子舉例甲烷磺醯氧基、三氟甲烷磺醯氧基、九氟丁烷磺醯氧基等之(氟)烷基磺醯氧基;苯磺醯氧基、甲苯磺醯氧基等之芳香族磺醯氧基等。
作為式(2B)表示之胺化合物,除了苯胺以外,舉例為與作為式(2A)表示之化合物所例示者。
式(2B)表示之胺化合物與式(3B)或(3B’)表示之含氟原子之化合物之饋入比,相對於胺化合物,含氟化合物可為當量以上,但宜為1~1.2當量。
作為反應所用之觸媒舉例為氯化銅、溴化銅、碘化銅等之銅觸媒;肆(三苯膦)鈀(Pd(PPh3)4)、雙(三苯膦)二氯鈀(Pd(PPh3)2Cl2)、雙(二亞苄基丙酮)鈀(Pd(dba)2)、三(二亞苄基丙酮)二鈀(Pd2(dba)3)、雙(三-第三丁基膦)鈀(Pd(P-t-Bu3)2)、乙酸鈀(Pd(OAc)2)等之鈀觸媒等之金屬觸媒。該等觸媒可單獨使用1種,亦可組合2種以上使用。
又,基於更有效率獲得成為目的之化合物之觀點,亦可與觸媒一起使用習知適當之配位基。作為此等配位基舉例為三苯膦、三-鄰-甲苯膦、二苯基甲基膦、苯基二甲基膦、三甲基膦、三乙基膦、三丁基膦、三-第三丁基膦、二-第三丁基(苯基)膦、二-第三丁基(4-二甲胺基苯基)膦、1,2-雙(二苯基膦醯基)乙烷、1,3-雙(二苯基膦醯基)丙烷、1,4-雙(二苯基膦醯基)丁烷、1,1’-雙(二苯基膦醯基)二茂鐵等之3級膦、亞磷酸三甲酯、亞磷酸三乙酯、亞磷酸三苯酯等之3級亞磷酸酯等。
觸媒之使用量相對於式(2B)表示之胺化合物1mol,可為0.01~0.5mol左右,較好為0.03~0.07mol左右。且,使用配位基時,其使用量相對於使用之金屬錯合物,可為0.1~5當量,較好為1~4當量。
作為鹼之具體例及較佳之鹼,舉例為與反應流程圖A所示之反應有關所例示者相同者。
反應溶劑只要對該種反應不帶來不良影響者即未特別限定,作為其具體例舉例為脂肪族烴類(戊烷、正己烷、正辛烷、正癸烷、十氫萘等)、鹵化脂肪族烴類(氯仿、二氯甲烷、二氯乙烷、四氯化碳等)、芳香族烴類(苯、硝基苯、甲苯、鄰-二甲苯、間-二甲苯、對-二甲苯、均三甲苯等)、鹵化芳香族烴類(氯苯、溴苯、鄰-二氯苯、間-二氯苯、對-二氯苯等)、醚類(二乙醚、二異丙醚、第三丁基甲基醚、四氫呋喃、二噁烷、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷等)、酮類(丙酮、甲基乙基酮、甲基異丁基酮、二-正丁基酮、環己酮等)、醯胺類(N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等)、內醯胺及內酯類(N-甲基吡咯啶酮、γ-丁內酯等)、尿素類(N,N-二甲基咪唑啶酮、四甲基脲等)、亞碸類(二甲基亞碸、環丁碸等)、腈類(乙腈、丙腈、丁腈等)等。該等溶劑可單獨使用1種,亦可混合2種以上。其中,較好為甲苯、鄰-二甲苯、間-二甲苯、對-二甲苯、二噁烷等。
反應溫度雖考慮所用原料化合物或觸媒種類或量、溶劑種類等,而自溶劑之熔點至沸點之範圍適當設
定,但通常為0~200℃左右,較好為20~150℃。且反應時間由於根據所用原料化合物或觸媒種類或量、反應溫度等而異故無法一概而論,但通常為1~12小時左右。
反應結束後,依據常用方法進行後處理,可獲得成為目的之寡聚苯胺衍生物。
式(3B)表示之含氟化合物可如下述反應流程圖D表示般,以鹵化劑鹵化式(4B)表示之化合物而製造。
(式中,R1~R10、A、X及a與前述相同)。
又,式(3B’)表示之含氟化合物可如下述反應流程圖E表示般,以擬鹵化劑擬鹵化式(4B’)表示之化合物而製造。
(式中,R1~R10、A、X’及a與前述相同)。
作為鹵化劑之具體例舉例為碘、N-碘琥珀醯
亞胺、苄基三甲基銨二氯碘、1,3-二碘-5,5-二甲基乙內醯脲、碘化氫、溴、N-溴琥珀醯亞胺、苄基三甲基銨三溴化物、N-溴乙醯胺、2-溴-2-氰基-N,N-二甲基乙醯胺、溴二甲基鋶溴化物、N-溴苯二醯亞胺、N-溴糖精、1,3-二溴-5,5-二甲基乙內醯脲、二溴異氰尿酸、5,5-二溴米氏酸、4-二甲胺基吡啶鎓溴化物全溴化物、吡啶鎓溴化物全溴化物、2,4,4,6-四溴-2,5-環己烷二烯酮、四丁基銨三溴化物、三甲基苯基銨三溴化物、三苯基膦二溴化物、氯、N-氯琥珀醯亞胺、苄基三甲基銨四氯碘化物、氯胺B、氯胺T.3水合物、鄰-氯胺、N-氯苯二醯亞胺、三聚氰氯、二氯胺T、二氯異氰尿酸鈉、三氯異氰尿酸等。
作為擬鹵化劑之具體例舉例為甲烷磺醯氯、甲烷磺醯溴、甲烷磺酸酐、三氟甲烷磺醯氯、三氟甲烷磺酸酐、九氟丁烷磺醯氯、(氟)烷基磺醯氯;苯磺醯氯、甲苯磺醯氯等。
鹵化劑或擬鹵化劑之使用量,相對於式(4B)或(4B’)表示之化合物1mol,可為1~3mol左右,但較好為1.0~1.1mol左右。
反應溶劑只要對該種反應不帶來不良影響者即未特別限定,作為其具體例舉例為與前述含氟原子之寡聚苯胺衍生物之製造方法中之溶劑具體例同樣者。其中,較好為N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、氯仿、二氯甲烷。
反應溫度雖考慮所用原料化合物或觸媒種類
或量、溶劑種類等,而自溶劑之熔點至沸點之範圍適當設定,但通常為0~200℃左右,較好為0~50℃。且反應時間由於根據所用原料化合物或觸媒種類或量、反應溫度而異故無法一概而論,但通常為1~12小時左右。
反應結束後,依據常用方法進行後處理,可獲得成為目的之化合物。
式(4B)表示之化合物可如下述反應流程圖F表示般,使式(2A’)表示之胺化合物與式(3A)表示之含氟酸鹵化物根據必要在與前述者同樣之鹼存在下反應而製造。
(式中,R1~R10、A、X及a與前述相同)。
作為式(2A’)表示之胺化合物,除了苯胺以外,舉例為與作為式(2A)表示之胺化合物所例示者同樣者。且,作為式(3A)表示之含氟酸鹵化物舉例為與前述同樣者。
反應溶劑只要對該種反應不帶來不良影響者
即未特別限定,作為其具體例舉例為與前述含氟原子之寡聚苯胺衍生物之製造方法中之溶劑具體例同樣者。其中,較好為N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、氯仿、二氯甲烷。
反應溫度雖考慮所用原料化合物或觸媒種類或量、溶劑種類等,而自溶劑之熔點至沸點之範圍適當設定,但通常為0~200℃左右,較好為0~50℃。且反應時間由於根據所用原料化合物或觸媒種類或量、反應溫度等而異故無法一概而論,但通常為1~12小時左右。
反應結束後,依據常用方法進行後處理,可獲得成為目的之化合物。
且,式(4B’)表示之化合物可如下述反應流程圖G表示般,使式(2A”)表示之胺化合物與式(3A)表示之含氟酸鹵化物根據必要在與前述者同樣之鹼存在下反應而製造。此等反應之參考文獻舉例為例如J.Med.Chem.,52(4),1115-1125,(2009)。
(式中,R1~R10、A、X及a與前述相同)。
反應溶劑只要對該種反應不帶來不良影響者即未特別限定,作為其具體例舉例為與前述含氟原子之寡聚苯胺衍生物之製造方法中之溶劑具體例同樣者。其中,較好為N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、氯仿、二氯甲烷。
反應溫度雖考慮所用原料化合物或觸媒種類或量、溶劑種類等,而自溶劑之熔點至沸點之範圍適當設定,但通常為0~200℃左右,較好為0~50℃。且反應時間由於根據所用原料化合物或觸媒種類或量、反應溫度而異故無法一概而論,但通常為1~12小時左右。
反應結束後,依據常用方法進行後處理,可獲得成為目的之化合物。
且,式(2A”)表示之胺化合物可藉由習知方法合成。若舉一例,則可根據下述反應流程圖H,合成期望鏈長之化合物。
以下,列舉式(1)表示之寡聚苯胺衍生物之具
體例,但不限定於此。又,表中之「R1~R10」、「A」及「k」係表示各行中所示之各化合物相關之式(1)中之規定者,例如式(E1)表示之化合物及式(E138)表示之化合物分別如下。
本發明之電荷輸送性塗料含有不含氟原子之電荷輸送性物質。作為不含氟原子之電荷輸送性物質,列舉為苯胺衍生物、噻吩衍生物、吡咯衍生物等之電荷輸送性寡聚物。前述電荷輸送性寡聚物之分子量通常為200~5,000,但基於調製供獲得電荷輸送性高的薄膜之塗料之觀點,較好為300以上,更好為400以上,又更好為500以上,基於調製供獲得平坦性高的薄膜之均一塗料之觀點,較好為4,000以下,更好3,000以下,又更好2,000以下。
前述電荷輸送性寡聚物中,考慮對有機溶劑之溶解性與所得薄膜之電荷輸送性之平衡時,較好為苯胺衍生物。作為苯胺衍生物舉例為日本特開2002-151272號公報中記載之寡聚苯胺衍生物、國際公開第2004/105446號中記載之寡聚苯胺化合物、國際公開第2008/032617號中記載之寡聚苯胺化合物、國際公開第2008/032616號中記載之寡聚苯胺化合物、國際公開第2013/042623號中記載之芳基二胺化合物等。
又,亦可較好地使用下述式(5)表示之苯胺衍生物。
式(5)中,X1表示-NY1-、-O-、-S-、-(CR17R18)L-或單鍵,但m或n為0時,表示-NY1-。
Y1分別獨立為氫原子、可經Z11取代之碳數1~20之烷基、碳數2~20之烯基或碳數2~20之炔基、或可經Z12取代之碳數6~20之芳基或碳數2~20之雜芳基。
碳數1~20之烷基、碳數2~20之烯基、碳數2~20之炔基、碳數6~20之芳基及碳數2~20之雜芳基之具體例舉例為與前述者相同者。
R17及R18分別獨立表示氫原子、氯原子、溴原子、碘原子、硝基、氰基、胺基、醛基、羥基、硫醇基、磺酸基、羧基、或可經Z11取代之碳數1~20之烷基、碳數2~20之烯基、碳數2~20之炔基、可經Z12取代之碳數6~20之芳基或碳數2~20之雜芳基,或表示-NHY2、-NY3Y4、-C(O)Y5、-OY6、-SY7、-SO3Y8、-C(O)OY9、-OC(O)Y10、-C(O)NHY11或-C(O)NY12Y13基。
Y2~Y13分別獨立表示可經Z11取代之碳數1~20之烷基、碳數2~20之烯基、或碳數2~20之炔基、或可經Z12取代之碳數6~20之芳基或碳數2~20之雜芳基。
Z11表示氯原子、溴原子、碘原子、硝基、氰基、胺基、醛基、羥基、硫醇基、磺酸基、羧基、或可經Z13取代之碳數6~20之芳基或碳數2~20之雜芳基。
Z12表示氯原子、溴原子、碘原子、硝基、氰基、胺基、醛基、羥基、硫醇基、磺酸基、羧基、或可經
Z13取代之碳數1~20之烷基、碳數2~20之烯基或碳數2~20之炔基。
Z13表示氯原子、溴原子、碘原子、硝基、氰基、胺基、醛基、羥基、硫醇基、磺酸基或羧基。
R17、R18及Y2~Y13之烷基、烯基、炔基、芳基及雜芳基舉例為與前述相同者。
該等中,作為R17及R18,較好為氫原子或可經Z11取代之碳數1~20之烷基,更好為氫原子或可經Z11取代之甲基,尤其最好為氫原子。
L表示-(CR17R18)-表示之2價基之數,較好為1~20之整數,但較好為1~10,更好為1~5,又更好為1~2,最好為1。又,L為2以上時,複數個R17可相互相同亦可不同,複數個R18亦可相互相同亦可不同。
尤其,作為X1較好為-NY1-或單鍵。且作為Y1,較好為氫原子或可經Z11取代之碳數1~20之烷基,更好為氫原子或可經Z11取代之甲基,最好為氫原子。
式(5)中,R11~R16分別獨立表示氫原子、氯原子、溴原子、碘原子、硝基、氰基、胺基、醛基、羥基、硫醇基、磺酸基、羧基、或可經Z11取代之碳數1~20之烷基、碳數2~20之烯基或碳數2~20之炔基、可經Z12取代之碳數6~20之芳基或碳數2~20之雜芳基,或表示-NHY2、-NY3Y4、-C(O)Y5、-OY6、-SY7、-SO3Y8、-C(O)OY9、-OC(O)Y10、-C(O)NHY11或-C(O)NY12Y13基(Y2~Y13表示與前述相同意義)。該等烷基、烯基、炔基、
芳基及雜芳基舉例為與前述相同者。
尤其,式(5)中,作為R11~R14,較好為氫原子、鹵原子、可經Z11取代之碳數1~10之烷基、或可經Z12取代之碳數6~14之芳基,更佳為氫原子或碳數1~10之烷基,最好全部為氫原子。
又,作為R15及R16,較好為氫原子、氯原子、溴原子、碘原子、可經Z11取代之碳數1~10之烷基、可經Z12取代之碳數6~14之芳基、或可經Z12取代之二苯基胺基(Y3及Y4為可經Z12取代之苯基的-NY3Y4基),更好為氫原子或二苯基胺基,再更好同時為氫原子或二苯基胺基。
該等中,較好係R11~R14為氫原子或碳數1~10之烷基,R15及R16為氫原子或二苯基胺基,X1為-NY1-或單鍵且Y1為氫原子或甲基之組合,更好係R11~R14為氫原子,R15及R16同時為氫原子或二苯基胺基,X1為-NH-或單鍵之組合。
式(5)中,m及n分別獨立表示0以上之整數,且滿足1≦m+n≦20,但考慮所得薄膜之電荷輸送性與苯胺衍生物之溶解性之平衡,較好滿足2≦m+n≦8,更好滿足2≦m+n≦6,又更好滿足2≦m+n≦4。
Y1~Y13及R11~R18中,Z11較好為氯原子、溴原子、碘原子、或可經Z13取代之碳數6~20之芳基,更好為氯原子、溴原子、碘原子、或可經Z13取代之苯基,最好為未存在(亦即為非取代)。
Z12較好為氯原子、溴原子、碘原子、或可經Z13取代之碳數1~20之烷基,更好為氯原子、溴原子、碘原子、可經Z13取代之碳數1~4之烷基,最好為未存在(亦即為非取代)。
Z13較好為氯原子、溴原子或碘原子,最好為未存在(亦即為非取代)。
Y1~Y13及R11~R18中,烷基、烯基及炔基之碳數較好為10以下,更好為6以下,又更好為4以下。且,芳基及雜芳基之碳數較好為14以下,更好為10以下,又更好為6以下。
又,前述苯胺衍生物之合成法並未特別限定,但舉例為Bulletin of Chemical Society of Japan,67,pp,1749-1752(1994)、Synthetic Metals,84,pp.119-120(1997)、Thin Solid Films,520(24),pp.7157-7163(2012)、國際公開第2008/032617號、國際公開第2008/032616號、國際公開第2008/129947號、國際公開第2013/084664號等所記載之方法。
式(5)表示之苯胺衍生物之具體例舉例為下述式表示者,但不限定於此。又,下述式中,DPA表示二苯基胺基,Ph表示苯基,TPA表示對-(二苯基胺基)苯基。
本發明之塗料中之電荷輸送性物質之含量,基於抑制電荷輸送性物質析出之觀點,塗料中較好為0.1~20質量%左右。且,由含氟原子之寡聚苯胺衍生物所成之電荷輸送物質與不含氟原子之電荷輸送性物質之使用比例,若考慮更提高所得有機EL元件之亮度特性,則對於由含氟原子之寡聚苯胺衍生物所成之電荷輸送物質1,以莫耳比計,不含氟原子之電荷輸送性物質較好為0.05~20左右,更好為0.5~5左右。
調製本發明之電荷輸送性塗料時所用之有機溶劑可使用可良好地溶解電荷輸送性物質及摻雜劑之高溶解性溶劑。
作為此種高溶解性溶劑,舉例為例如環己酮、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N,N-二甲基異丁醯胺、N-甲基吡咯啶酮、1,3-二甲基-2-咪唑啶酮等之有機溶劑,但不限定於此。該等溶劑可單獨使用1種或可混合2種以上使用,其使用量可為塗料中所用之全部溶劑中之5~100質量%。
又,較好電荷輸送性物質及摻雜劑均完全溶解於前述溶劑或成為均一分散狀態,更好完全溶解。
又,本發明中,塗料於25℃具有為10~200mPa‧s,特別是35~150mPa‧s之黏度,可含有至少1種在常壓(大氣壓)下沸點50~300℃,尤其是150~250℃之高黏度有機溶劑。藉由添加此溶劑,可容易地調整塗料黏度,可再現性良好地給予平坦性高之薄膜,可根據所用塗佈方法調製塗料。
作為高黏度有機溶劑舉例為例如環己醇、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,但不限於此。
本發明之塗料中高黏度有機溶劑相對於所用之溶劑全體之添加比例,較好為不使固體析出之範圍內,在不使固體析出,添加比例較好為5~90質量%。
進而,為了提高對基板之濡濕性、調整溶劑之表面張力、調整極性、調整沸點等之目的,亦可以塗料中使用之全部溶劑中1~90質量%,較好1~50質量%之比
例混合其他溶劑。
作為此等溶劑,舉例為例如丙二醇單甲醚、二乙二醇單丁醚、二乙二醇二乙醚、二乙二醇單甲醚、二乙二醇二甲醚、二乙二醇單乙醚乙酸酯、二乙二醇單丁醚乙酸酯、二丙二醇單甲醚、丙二醇單甲醚乙酸酯、二乙二醇單乙醚、二丙酮醇、γ-丁內酯、乳酸乙酯、乙酸正己酯等,但不限於此。該等溶劑可單獨使用1種或混合2種以上使用。
本發明之塗料之黏度係根據所製作之薄膜厚度等或固體成分濃度適當設定,但通常在25℃為1~50mPa‧s。又,本發明之電荷輸送性塗料之固體成分濃度係考量塗料之黏度及表面張力等,或製作之薄膜之厚度等適當設定,但通常為0.1~10.0質量%左右,若考慮提高塗料之塗佈性,則較好為0.5~5.0質量%,更好為1.0~3.0質量%。又,所謂固體成分意指塗料成分中有機溶劑除外者。
本發明之電荷輸送性塗料,根據所得薄膜之用途,以提高其電荷輸送能等之目的亦可包含摻雜劑。摻雜劑只要能溶解於塗料中使用之至少一種溶劑者即可無特別限制,可使用無機系之摻雜劑、有機系之摻雜劑之任一種。無機系之摻雜劑及有機系之摻雜劑可單獨使用1種亦可混合2種以上使用。
本發明之電荷輸送性塗料含摻雜劑時,其含量對於不含氟原子之電荷輸送性物質1,以莫耳比計,較好為0.01~20.0左右,更好為0.4~5.0左右。
作為無機系之摻雜劑列舉為氯化氫、硫酸、硝酸、磷酸等之無機酸;氯化鋁(III)(AlCl3)、四氯化鈦(IV)(TiCl4)、三溴化硼(BBr3)、三氟化硼醚錯合物(BF3‧OEt2)、氯化鐵(III)(FeCl3)、氯化銅(II)(CuCl2)、五氯化銻(V)(SbCl5)、五氟化銻(V)(SbF5)、五氟化砷(V)(AsF5)、五氟化磷(PF5)、三(4-溴苯基)鋁六氯銻酸鹽(TBPAH)等之金屬鹵化物;Cl2、Br2、I2、ICl、ICl3、IBr、IF4等之鹵素;磷鉬酸、磷鎢酸等之雜多酸等。該等中,較好為磷鉬酸、磷鎢酸等之雜多酸。
作為有機矽之摻雜劑列舉為苯磺酸、甲苯磺酸、對-苯乙烯磺酸、2-萘磺酸、4-羥基苯磺酸、5-磺基水楊酸、對-十二烷基苯磺酸、二己基苯磺酸、2,5-二己基苯磺酸、二丁基萘磺酸、6,7-二丁基-2-萘磺酸、十二烷基萘磺酸、3-十二烷基-2-萘磺酸、己基萘磺酸、4-己基-1-萘磺酸、辛基萘磺酸、2-辛基-1-萘磺酸、己基萘磺酸、7-己基-1-萘磺酸、6-己基-2-萘磺酸、二壬基萘磺酸、2,7-二壬基-4-萘磺酸、二壬基萘二磺酸、2,7-二壬基-4,5-萘二磺酸、國際公開第2005/000832號記載之1,4-苯并二噁烷二磺酸化合物、國際公開第2006/025342號記載之芳基磺酸化合物、國際公開第2009/096352號記載之芳基磺酸化合物、聚苯乙烯磺酸等之芳基磺酸化合物等。
又,下述式(6)或(7)表示之芳基磺酸化合物亦可較好地使用作為摻雜劑。
式(6)中,A1表示-O-或-S-,較好為-O-。A2表示萘環或蒽環,但較好為萘環。A3表示2~4價之全氟聯苯基,j1表示A1與A3之鍵結數,為滿足2≦j1≦4之整數,但較好A3表示2價之全氟聯苯基,且j1為2。j2表示鍵結於A2之磺酸基數,且為滿足1≦j2≦4之整數,但較好為2。
式(7)中,A4~A8分別獨立表示氫原子、鹵原子、氰基、碳數1~20之烷基、碳數1~20之鹵化烷基或碳數2~20之鹵化烯基,但A4~A8中至少3個為鹵原子。i表示鍵結於萘環之磺酸基數,且為滿足1≦i≦4之整數,但較好為2~4,更好為2。
作為碳數1~20之鹵化烷基舉例為三氟甲基、2,2,2-三氟乙基、全氟乙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、全氟丙基、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、全氟丁基等。作為碳數2~20之鹵化烯基舉例為全氟乙烯基、1-全氟丙烯基、全氟烯丙基、全氟丁烯基等。
作為鹵原子、碳數1~20之烷基舉例為與前述相同者,作為鹵原子較好為氟原子。
該等中,A4~A8較好為氫原子、鹵原子、氰基、碳數1~10之烷基、碳數1~10之鹵化烷基或碳數2~10之鹵化烯基,且A4~A8中至少3個為氟原子,更好為氫原子、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,又更好為氫原子、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。
又,所謂全氟烷基係烷基之氫原子全部取代為氟原子之基,所謂全氟烯基係烯基之氫原子全部取代為氟原子之基。
進而,下述式(8)表示之芳基磺酸化合物亦可較好地作為摻雜劑使用。
[式中,Ar表示式(9)或(10)表示之基。
(式中,p表示1~5之整數,q表示1~7之整數)]。
述式(8)表示之芳基磺酸化合物可藉由使式(11)表示之胺化合物與式(12)表示之酸鹵化物反應而獲得式(8’)表示之芳基磺酸鹽,並藉離子交換處理該鹽而獲得。
[式中,Ar及X與前述相同,Ar’表示式(9’)或(10’)表示之基,
(式中,p及q與前述相同,M表示鈉、鉀等之鹼金屬原子)]。
作為式(11)表示之胺化合物,舉例為苯胺-2,4-二磺酸二鈉、苯胺-2,5-二磺酸二鈉、8-胺基-萘-1,5-二磺酸二鈉、2-胺基-萘-1,5-二磺酸二鈉、2-胺基-萘-3,6-二磺酸二鈉、7-胺基萘-1,5-二磺酸二鈉、7-胺基萘-2,4-二磺酸二鈉、7-胺基萘-1,3-二磺酸二鈉等,但不限於此。又,式
(11)表示之胺化合物亦可使用水合物。
作為式(12)表示之酸鹵化物舉例為苯甲醯氯、苯甲醯溴等。
反應溶劑較好為非質子性極性有機溶劑,例如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-咪唑啶酮、二甲基亞碸、四氫呋喃、二噁烷等。基於反應後之反應溶劑之去除容易性之觀點,較好為N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、四氫呋喃、二噁烷等。
反應溫度通常可為自-50℃至使用之溶劑沸點,但較好為0~140℃之範圍。反應時間通常為0.1~100小時。
反應結束後,藉由過濾、餾除反應溶劑等回收式(8’)表示之芳基磺酸鹽後,藉由例如陽離子交換樹脂將磺酸鹽質子化,可製造式(8)表示之芳基磺酸化合物。
又,式(12)表示之酸鹵化物可藉由使苯甲酸與例如亞硫醯氯或草醯氯、磷醯氯、硫醯氯、三氯化磷、五氯化磷等之親電子之鹵化劑反應而獲得。
作為較佳之摻雜劑之具體例,舉例為磷鉬酸、磷鎢酸及以下所示者,但不限於此。
又,本發明之電荷輸送性塗料,在不損及苯發明效果之範圍內,亦可含習知之其他電荷輸送性物質。
電荷輸送性塗料之調製法並未特別限制,舉例為例如將本發明之寡聚苯胺衍生物溶解於高溶解性溶劑,於其中添加高黏度有機溶劑之方法,或混合高溶解性溶劑與高黏度有機溶劑,於其中溶解本發明之寡聚苯胺衍生物之方法。
本發明中,電荷輸送性塗料基於再現性良好地獲得平坦性更高之薄膜之觀點,期望將電荷輸送性物質、摻雜劑等溶解於有機溶劑後,使用次微米等級之過濾器等過濾。
藉由將本發明之電荷輸送性塗料塗佈於基材上並燒
成,可於基材上形成電荷輸送性薄膜。
塗料之塗佈方法舉例為浸漬法、旋塗法、轉印印刷法、輥塗佈法、刷毛塗佈法、噴墨法、噴霧法、狹縫塗佈法等,但不限於此。較好根據塗佈方法,調節塗料之黏度及表面張力。
又,使用本發明之塗料時,燒成氛圍亦未特別限定,不僅可為大氣氛圍,即使於氮等之惰性氣體或真空中,亦可獲得具有均一成膜面及電荷輸送性之薄膜,但考慮再現性良好地獲得高電荷輸送性薄膜時,較好為大氣氛圍。
燒成溫度可考慮所得薄膜之用途、對所得薄膜賦予之電荷輸送性程度等,而於100~260℃左右之範圍內適當設定,但所得薄膜使用作為有機EL元件之電洞注入層時,較好為140~250℃左右,更好為145~240℃左右。
且燒成時間由於根據燒成溫度而變化故無法一概而論,但通常為1分鐘~1小時左右。
又,燒成時,為展現更高均一成膜性而在基材上進行反應,亦可施以2階段以上之溫度變化。加熱只要使用例如加熱板或烘箱等適當機器進行即可。
電荷輸送性薄膜之膜厚並未特別限定,但在有機EL元件內使用作為電洞注入層時,較好為5~200nm。改變膜厚之方法有改變塗料中之固體成分濃度,改變塗佈時之基板上之溶液量等方法。
本發明之電荷輸送性薄膜可較好地於有機EL元件中作為電洞注入層使用,但亦可使用作為電洞注入輸送層等之電荷輸送性功能層。
本發明之有機EL元件係具有一對電極,於該等電極間具有前述之本發明電荷輸送性薄膜者。
作為有機EL元件之代表構成舉例為下述(a)~(f),但不限於此。又,下述構成中,根據需要,於發光層與陽極之間亦可設置電子阻斷層,於發光層與陰極之間設置電洞(hole)阻斷層等。且,電洞注入層、電洞輸送層或電洞注入輸送層亦可兼具作為電子阻斷層等之功能,電子注入層、電子輸送層或電子注入輸送層亦可兼具作為電洞(hole)阻斷層等之功能。
(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
所謂「電洞注入層」、「電洞輸送層」及「電洞注入輸送層」係形成於發光層與陽極之間之層,具有將電洞自陽極輸送至發光層之功能者。於發光層與陽極之間,僅設置1層電洞輸送性材料之層時,其為「電洞注入輸送層」,於發光層與陽極之間,設置2層以上之電洞輸送性材料之層時,接近陽極之層為「電洞注入層」,其以外之層為「電洞輸送層」。尤其,電洞注入層及電洞注入輸送層係使用不僅自陽極之電洞接收性優異,對電洞輸送層及發光層各者之電洞注入性亦優異之薄膜。
所謂「電子注入層」、「電子輸送層」及「電子注入輸送層」係形成於發光層與陰極之間之層,具有將電子自陰極輸送至發光層之功能者。於發光層與陰極之間,僅設置1層電子輸送性材料之層時,其為「電子注入輸送層」,於發光層與陰極之間,設置2層以上之電子輸送性材料之層時,接近陰極之層為「電子注入層」,其以外之層為「電子輸送層」。
所謂「發光層」係具有發光功能之有機層,於採用摻雜系統時,包含主體材料與摻雜劑材料。此時,主體材料具有主要促進電子與電洞之再結合,將激子封閉於發光層內之功能,摻雜劑材料具有將再結合所得之激子有效率地發光之功能。磷光元件時,主體材料具有將主要由摻雜劑生成之激子封閉於發光層內之功能。
使用本發明之電荷輸送性塗料作為製作有機EL元件時之使用材料或製作方法舉例為如下述者,但不
限定於此。
使用之電極基板較好為以洗劑、醇、純水等預先進行液體洗淨而淨化,例如陽極基板較好在使用前進行UV臭氧處理、氧-電漿處理等之表面處理。但陽極材料以有機物作為主成分時,亦可不進行表面處理。
由本發明之電荷輸送性塗料獲得之薄膜為電洞輸送層時之本發明之有機EL元件之製作方法之一例如以下。
藉由前述方法,將本發明之電荷輸送性塗料塗佈於陽極基板上並燒成,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係根據所用材料之特性,以蒸鍍法或塗佈法(溼式製程)之任一種形成即可。
作為陽極材料列舉為由以銦錫氧化物(ITO)、銦鋅氧化物(IZO)為代表之透明電極,或以鋁為代表之金屬或該等之合金等所構成之金屬陽極,較好為進行平坦化處理者。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。
又,構成金屬陽極之其他金屬列舉為鍶、鈦、釩、鉻、錳、鐵、鈷、鎳、銅、鋅、鎵、釔、鋯、鈮、鉬、釕、銠、鈀、鎘、銦、鍶、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,
但並不限於此。
作為形成電洞輸送層之材料列舉為(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-螺聯茀、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-螺聯茀、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-螺聯茀、9,9-雙[4-(N,N-雙-聯苯-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-螺聯茀、N,N’-雙(菲-9-基)-N,N’-雙(苯基)-聯苯胺、2,2’-雙[N,N-雙(聯苯-4-基)胺基]-9,9-螺聯茀、2,2’-雙(N,N-二苯基胺基)-9,9-螺聯茀、二-[4-(N,N-二(對-甲苯基)胺基)-苯基]環己烷、2,2’,7,7’-肆(N,N-二(對-甲苯基)胺基)-9,9-螺聯茀、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(間-
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(對-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)等三芳基胺類,5,5”-雙-{4-[雙(4-甲基苯基)胺基]苯基}-2,2’:5’,2”-三聯噻吩(BMA-3T)等寡聚噻吩類等之電洞輸送性低分子材料等。
形成發光層之材料列舉為參(8-羥基喹啉(quinolinato))鋁(III)(Alq3)、雙(8-羥基喹啉)鋅(II)(Znq2)、雙(2-甲基-8-羥基喹啉)-4-(對-苯基酚酸)鋁(III)(BAlq)、4,4’-雙(2,2-二苯基乙烯基)聯苯、9,10-二(萘-2-基)蒽、2-第三丁基-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-螺聯茀-2-基)-9,9-螺聯茀、2,7-雙(9,9-螺聯茀-2-基)-9,9-螺聯茀、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-螺聯茀、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-螺聯茀、1,4-二(芘-1-基)苯、1,3-二(芘-1-基)苯、6,13-二(聯苯-4-基)五并苯、3,9-二(萘-2-基)苝、3,10-二(萘-2-基)苝、參[4-(苝基)-苯基]胺、10,10’-二(聯苯-4-基)-9,9’-聯蒽、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、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-螺聯茀、2,7-雙(咔唑-9-基)-9,9-二(對-甲苯基)茀、9,9-雙[4-(咔唑-9-基)-苯基]茀、2,7-雙(咔唑-9-基)-9,9-螺聯茀、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)-對-聯三苯、4,4’-二(三苯基矽烷基)聯苯、9-(4-第三丁基苯基)-3,6-雙(三苯基矽烷基)-9H-咔唑、9-(4-第三丁基苯基)-3,6-二三苯甲基-9H-咔唑、9-(4-第三丁基苯基)-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-螺聯茀-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(二苯基膦基)-9-苯基-9H-茀-9-基)-9-苯基-9H-咔唑、4,4,8,8,12,12-六(對-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-菲繞啉、2,2’-雙(4-(咔唑-9-基)苯基)聯苯、2,8-雙(二苯基膦基)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-(二苯基膦基)-9-(4-(二苯基膦基)苯基)-9H-咔唑、3,6-雙[(3,5-二苯基)苯基]-9-苯基咔唑等。藉由該等材料與發光性摻雜物共蒸鍍,亦可形成發光層。
作為發光性摻雜劑列舉為3-(2-苯并噻唑基)-7-(二乙胺基)香豆素、2,3,6,7-四氫-1,1,7,7-四甲基-1H,5H,11H-10-(2-苯并噻唑基)喹嗪并[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)(乙醯基丙酮酸]銥(III)(Ir(ppy)2(acac))、參[2-(對-甲苯基)吡啶]銥(III)(Ir(mppy)3)、9,10-雙[N,N-二(對-甲苯基)胺基]蒽、9,10-雙[苯基(間-甲苯基)胺基]蒽、雙[2-(2-羥基苯基)苯并噻唑]鋅(II)、N10,N10,N10,N10-四(對-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-9,9’-聯蒽-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-第三丁基苝、1,4-雙[2-(3-N-乙基咔唑基)乙烯基]苯、4,4’-雙[4-(二-對-甲苯基胺基)苯乙烯基]聯苯、4-(二-對-甲苯基胺基)-4’-[(二-對-甲苯基胺基)苯乙烯基]二苯基乙烯、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(2,4-二氟苯基吡啶酸根)肆(1-吡唑基)硼酸銥(III)、N,N’-雙(萘-2-基)-N,N’-雙(苯基)-參(9,9-二甲基伸茀基)、2,7-雙{2-[苯基(間-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-苯基苯胺、fac-銥(III)參(1-苯基-3-甲基苯并咪唑-2-亞基-C,C2)、mer-銥(III)參(1-苯基-3-甲基苯并咪唑-2-亞基-C,C2)、2,7-雙[4-(二苯基胺基)苯乙烯基]-9,9-螺聯茀、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(2,4-二茀苯基吡啶酸根)(5-(吡啶-2-基)-1H-四唑酸根)銥(III)、雙(3-三氟甲基-5-(2-吡啶)吡唑)((2,4-二氟苄基)二苯基膦酸根)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑酸根)(苄基二苯基膦酸根)銥(III)、雙(1-(2,4-二氟苄基)-3-甲基苯并咪唑鎓)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑酸根)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑酸根)(4’,6’-二氟苯基吡啶酸根)銥(III)、雙(4’,6’-二氟吡啶酸根)(3,5-雙(三氟甲基)-2-(2’-吡啶基)吡咯酸根)銥(III)、雙(4’,6’-二氟苯基吡啶酸根)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑酸根)銥(III)、(Z)-6-均三甲苯基-N-(6-均三甲苯基喹啉-2(1H)-亞基)喹啉-2-胺-BF2、(E)-2-(2-(4-(二甲胺基)苯乙烯基)-6-甲基-4H-吡喃-4-亞基)丙二腈、4-(二氰基亞甲基)-2-甲基-6-九洛尼啶(julolidyl)-9-烯基-4H-吡喃、4-(二氰基亞甲基)-2-甲基-6-(1,1,7,7-四甲基九洛尼啶-9-烯基)-4H-吡喃、4-(二氰基亞甲基)-2-第三丁基-6-(1,1,7,7-四甲基九洛尼啶-4-基-乙烯基)-4H-吡喃、參(二苯甲醯基甲烷)菲繞啉銪
(III)、5,6,11,12-四苯基萘、雙(2-苯并[b]噻吩-2-基-吡啶)(乙醯基丙酮酸根)銥(III)、參(1-苯基異喹啉)銥(III)、雙(1-苯基異喹啉)(乙醯基丙酮酸根)銥(III)、雙[1-(9,9-二甲基-9H-茀-2-基)-異喹啉](乙醯基丙酮酸根)銥(III)、雙[2-(9,9-二甲基-9H-茀-2-基)喹啉](乙醯基丙酮酸根)銥(III)、參[4,4’-二-第三丁基-(2,2’)-聯吡啶]釕(III)‧雙(六氟磷酸鹽)、參(2-苯基喹啉)銥(III)、雙(2-苯基喹啉)(乙醯基丙酮酸根)銥(III)、2,8-二-第三丁基-5,11-雙(4-第三丁基苯基)-6,12-二苯基四并苯、雙(2-苯基苯并噻唑基)(乙醯基丙酮酸根)銥(III)、5,10,15,20-四苯基四苯并卟啉鉑、鋨(II)雙(3-三氟甲基-5-(2-吡啶)-吡唑酸根)二甲基苯基膦、鋨(II)雙(3-(三氟甲基)-5-(4-第三丁基吡啶基)-1,2,4-三唑酸根)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-第三丁基吡啶基)-1,2,4-三唑酸根)二甲基苯基膦、雙[2-(4-正己基苯基)喹啉](乙醯基丙酮酸根)銥(III)、參[2-(4-正己基苯基)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)吡啶酸根)銥(III)、雙(2-(9,9-二乙基-茀-2-基)-1-苯基-1H-苯并[d]咪唑酸根)(乙醯基丙酮酸根)銥(III)、雙(2-苯基吡啶)(3-(吡啶-2-基)-2H-色烯-2-酸根)銥(III)、雙(2-苯基喹啉)(2,2,6,6-四甲基庚-3,5-二酸根)銥(III)、雙(苯基異喹啉)(2,2,6,6-四甲基庚-3,5-二酸根)銥(III)、銥(III)雙(4-苯基噻吩并[3,2-c]吡啶酸根-N,C2)乙醯基丙酮酸鹽、(E)-2-(2-第三丁基-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-亞基)丙二腈、雙(3-三氟甲基-5-(1-異喹啉)吡唑酸根)(甲基二苯基膦)釕、雙[(4-正己基苯基)異喹啉](乙醯基丙酮酸根)銥(III)、鉑(II)八乙基卟啉、雙(2-甲基二苯并[f,h]喹喔啉)(乙醯基丙酮酸根)銥(III)、參[(4-正己基苯基)喹喔啉]銥(III)等。
作為形成電子輸送層之材料列舉為8-羥基喹啉酸鋰、2,2’,2”-(1,3,5-苯三基)-參(1-苯基-1-H-苯并咪唑)、2-(4-聯苯)-5-(4-第三丁基苯基)-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-羥基喹啉)-4-(苯基酚酸)鋁、1,3-雙[2-(2,2'-聯吡啶-6-基)-1,3,4-噁二唑-5-基]苯、6,6'-雙[5-(聯苯-4-基)-1,3,4-噁二唑-2-基]-2,2’-聯吡啶、3-(4-聯苯基)-4-苯基)-5-第三丁基苯基-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’-聯吡啶-6-基)-1,3,4-噁二唑-5-基]-9,9-二甲基茀、1,3-雙[2-(4-第三丁基苯基)-1,3,4-噁二唑-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-咪唑并[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[(間-吡啶基)-苯-3-基]聯苯、1,3,5-參[(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-羥基苯并[h]喹啉酸根)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列舉為氧化鋰(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、乙醯基丙酮酸鋰(Li(acac))、乙酸鋰、苯甲酸鋰等。
作為陰極材料列舉為鋁、鎂-銀合金、鋁-鋰合金、鋰、鈉、鉀、銫等。
又,由本發明之電荷輸送性塗料所得之薄膜為電洞注入層時之本發明之有機EL元件之製作方法之其他例如以下。
上述有機EL元件製作中,代替進行電洞輸送層、發光層、電子輸送層、電子注入層之真空蒸鍍操作,亦可藉由依序形成電洞輸送層、發光層製作具有利用本發明之電荷輸送性塗料形成之電洞輸送性薄膜之有機EL元件。具體而言,在陽極基板塗佈本發明之電荷輸送性塗料且以上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,進而蒸鍍陰極材料而成為有機EL元件。
使用之陰極及陽極材料可使用與前述者相同者,且可進行相同之洗淨處理、表面處理。
作為電洞輸送層及發光層之形成法列舉為將電洞輸送性高分子材料或發光性高分子材料、或於該等中添加摻雜劑之材料中添加溶劑而溶解或均一分散,且分別塗佈於電洞注入層或電洞輸送層上後,燒成而成膜之方
法。
作為電洞輸送性高分子材料列舉為聚[(9,9-二己基茀-2,7-二基)-共聚-(N,N’-雙{對-丁基苯基}-1,4-二胺基伸苯基)]、聚[(9,9-二辛基茀-2,7-二基)-共聚-(N,N’-雙{對-丁基苯基}-1,1’-聯伸苯基-4,4-二胺)]、聚[(9,9-雙{1’-戊烯-5’-基}茀-2,7-二基)-共聚-(N,N’-雙{對-丁基苯基}-1,4-二胺基伸苯基)]、以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[(9,9-二辛基茀-2,7-二基)-共聚-(4,4’-(N-(對-丁基苯基))二苯基胺)]等。
作為發光性高分子材料列舉為聚(9,9-二烷基茀)(PDAF)等聚茀衍生物、聚(2-甲氧基-5-(2’-乙基己氧基)-1,4-伸苯基伸乙烯基)(MEH-PPV)等聚伸苯基伸乙烯基衍生物、聚(3-烷基噻吩)(PAT)等聚噻吩衍生物、聚乙烯基咔唑(PVCz)等。
作為溶劑列舉為甲苯、二甲苯、氯仿等,溶解或均一分散法列舉為攪拌、加熱攪拌、超音波分散等方法。
塗佈方法並無特別限制,列舉為噴墨法、噴霧法、浸漬法、旋塗法、轉印印刷法、輥塗法、刷毛塗佈等。又,塗佈較好在氮氣、氬氣等惰性氣體下進行。
作為燒成方法列舉為在惰性氣體下或真空中,以烘箱或加熱板加熱之方法。
由本發明之電荷輸送性塗料所得之薄膜為電洞注入輸送層時之本發明之有機EL元件之製作方法之一
例如以下。
在陽極基板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之形成方法及具體例舉例為與前述者相同者。
作為陽極材料、形成發光層、發光性摻雜劑、電子輸送層及電子阻斷層之材料、陰極材料舉例為與前述者相同者。
又,於電極及前述各層之間之任意之間,根據需要亦可設置電洞阻斷層、電子阻斷層等。例如作為電子阻斷層之材料舉例為叁(苯基吡唑)銥等。
構成陽極與陰極及形成於該等之間之層之材料,由於製造具備底部發射構造、頂部發射構造之哪一者之元件並不相同,故係考慮該點而選擇適當材料。
通常,於底部發射構造之元件,基板側係使用透明陽極,於基板側取出光,相對於此,於頂部發射構造之元件,係使用由金屬所成之反射陽極,自位於與基板相反方向之透明電極(陰極)側取出光。因此,若針對例如陽極材料而言,製造底部發射構造之元件時使用ITO等之透明陽極,於製造頂部發射構造之元件時使用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,亦可依據規定方法根據需要與捕水劑一起封入。
以下,列舉實施例及比較例更具體說明本發明,但本發明並不受限於下述之實施例。又,使用之裝置如以下。
(1)1H-NMR測定:日本電子(股)製,JNM-ECP300 FT NMR SYSTEM
(2)基板洗淨:長州產業(股)製,基板洗淨裝置(減壓電漿方式)
(3)塗料之塗佈:MIKASA(股)製,旋轉塗佈器MS-A100
(4)膜厚測定:小坂研究所(股)製,微細形狀測定機SURFCORDAR ET-4000
(5)EL元件之製作:長州產業(股)製,多功能蒸鍍裝置系統C-E2L1G1-N
(6)EL元件之亮度等之測定:TEC WORLD(有)製,I-V-L測定系統
(7)EL元件之壽命等之測定:EHC(股)製,有機EL亮度壽命評價系統PEL-105S
於燒瓶內,饋入四苯胺3.0g、2,3,4,5-四氟苯甲醯氯1.91g及N,N-二甲基乙醯胺60g後,對燒瓶內進行氮氣置換,於室溫攪拌1小時。
攪拌結束後,添加30mL之5mol/L氫氧化鈉水溶液,進而攪拌30分鐘。於反應液中混合乙酸乙酯及飽和食鹽水,直至pH為7,進行分液處理(3次)。所得有機層以硫酸鈉乾燥,其次進行減壓濃縮。於該濃縮液中添加THF 15mL。將該溶液滴加於異丙醇210mL中,所得漿料於室溫攪拌30分鐘。
最後,過濾漿料,使所得過濾物乾燥,獲得目的之寡聚苯胺衍生物A(收量2.94g)。1H-NMR測定結果示於以下。
1H-NMR(400MHz,DMSO-d6)δ[ppm]:10.35(s,1H),7.83(s,1H),7.79-7.68(m,3H),7.49(d,J=8.0Hz,2H),7.15(t,J=8.0Hz,2H),7.01-6.90(m,12H),6.68(t,J=8.0Hz,1H)
於燒瓶內,饋入4-碘苯胺2.54g、N,N-二甲基乙醯胺25mL及三乙胺1.6mL後,進行氮氣置換,滴加2,3,4,5-四氟苯甲醯氯2.72g,於室溫攪拌2小時。攪拌結束後,將反應液滴加於離子交換水250mL中,於室溫攪拌1小時。過濾懸浮液,獲得2,3,4,5-四氟-N-(4-碘苯基)苯甲醯胺(收量3.67g)。
其次,於燒瓶內,饋入N1-苯基苯-1,4-二胺0.63g、2,3,4,5-四氟-N-(4-碘苯基)苯甲醯胺1.51g、Pd(dba)2 80mg及t-BuONa 1.67g後,進行氮氣置換,添加甲苯20mL及另外預先調製之苯基-二(第三丁基)膦之甲苯溶液(濃度:75g/L)0.82mL,於50℃攪拌3.5小時。使反應液冷卻至室溫後,進行過濾,於過濾物中添加N,N-二甲基甲醯胺20mL調製溶液,將該溶液滴加於離子交換水中,於室溫進行攪拌。過濾懸浮物,使所得過濾物乾燥。針對乾固之
固體,使用1,4-二噁烷進行再結晶,獲得目的之寡聚苯胺衍生物B(收量0.49g)。
於燒瓶內,饋入N1-苯基本-1,4-二胺5.01g、N,N-二甲基乙醯胺25mL及三乙胺4.5mL後,進行氮氣置換,滴加2,3,4,5-四氟苯甲醯氯6.36g,於室溫攪拌2小時。攪拌結束後,將反應液滴加於離子交換水250mL中,於室溫攪拌1小時。過濾懸浮液,於所得過濾物中添加1,4-二噁烷10g及乙醇15g,進行再結晶,獲得目的之寡聚苯胺衍生物C(收量3.36g)。1H-NMR測定結果示於以下。
1H-NMR(400MHz,DMSO-d6)δ[ppm]:10.41(s,1H),8.13(s,1H),7.71-7.73(m,1H),7.53(d,J=7.2Hz,2H),7.18(t,J=7.6Hz,2H),7.04(d,J=7.2Hz,2H),7.01(d,J=7.6Hz,2H),6.74-6.78(m,1H).
於燒瓶內,饋入寡聚苯胺衍生物C 9.85g、N,N-二甲基甲醯胺100mL及N-溴琥珀醯亞胺5.08g後,進行氮氣置換,於室溫攪拌3小時。攪拌結束後,將反應液滴加於離子交換水1L中,於室溫攪拌。進行懸浮液之過濾,使過濾物乾燥後,於所得過濾物中添加1,4-二噁烷10g及乙醇15g,進行再結晶,獲得目的之寡聚苯胺衍生物C’(收量6.55g)。1H-NMR測定結果示於以下。
1H-NMR(400MHz,DMSO-d6)δ[ppm]:8.16-8.19(m,1H),7.83-7.86(m,1H),7.53(d,J=8.8Hz,2H),7.36(d,J=8.8Hz),7.08(d,J=8.8Hz,2H),6.93(d,J=8.8Hz,2H).
於燒瓶內,饋入寡聚苯胺衍生物C’1.31g、N1-苯基苯-1,4-二胺0.50g、Pd(dba)2 63mg及t-BuONa 1.34g,進行氮氣置換後,添加甲苯15mL及另外預先調製之苯基-二(第三丁基)膦之甲苯溶液(濃度:88g/L)0.55mL,於50℃攪拌5.5小時。使反應液冷卻至室溫後,進行過濾,將所得過濾物溶解於N,N-二甲基甲醯胺中,進行過濾。將該濾液滴加於離子交換水中,於室溫攪拌。過濾所得懸浮物,使過濾物乾燥後,以1,4-二噁烷進行再結晶,獲得目的之寡聚苯胺衍生物A(收量0.72g)。1H-NMR測定結果與合成例1相同。
於燒瓶內饋入4,4’-二胺基二苯基胺(3.18g,16.0mmol)、4-溴三苯基胺(11.4g,35.2mmol)、Pd(dba)2(0.185g,0.322mmol)、t-BuONa(3.38g,35.2mmol),進行氮氣置換後,添加甲苯(200mL)及PhP(t-Bu)2(0.142g,0.639mmol),於80℃攪拌5小時。反應混合物冷卻至室溫
後,添加水停止反應,藉由分液分離有機層。有機層以飽和食鹽水洗淨,以MgSO4乾燥後,減壓餾除溶劑,獲得粗產物。所得粗產物以矽膠管柱層析(甲苯/乙酸乙酯)純化,獲得目的之苯胺衍生物X(收量:6.83g)。
在氮氣氛圍下,將合成例1中合成之寡聚苯胺衍生物A 0.051g、下述式表示之苯基四苯胺0.169g及下述式表示之芳基磺酸A 0.344g溶解於1,3-二甲基-2-咪唑啶酮(DMI)6.7g、環己醇(CHA)10g及丙二醇(PG)3.3g之混合溶劑中,調製電荷輸送性塗料A。又,苯基四苯胺係依據Bulletin of Chemical Society of Japan,1994,67,pp.1749-1752中記載之方法合成。且芳基磺酸A係依據國際公開第2006/025342號合成。
在氮氣氛圍下,將合成例1中合成之寡聚苯胺衍生物
A 0.083g、合成例6中合成之苯胺衍生物X0.139g及磷鎢酸(關東化學(股)製)0.694g溶解於DMI 6.7g、CHA 10g及PG 3.3g之混合溶劑中,調製電荷輸送性塗料B。
在氮氣氛圍下,將合成例1中合成之寡聚苯胺衍生物A 0.051g、合成例6中合成之苯胺衍生物X0.129g及芳基磺酸A 0.383g溶解於DMI 6.7g、CHA 10g及PG 3.3g之混合溶劑中,調製電荷輸送性塗料C。
在氮氣氛圍下,將合成例1中合成之寡聚苯胺衍生物A 0.073g、N,N’-二苯基聯苯胺(東京化成工業(股)製)0.362g及芳基磺酸A 0.384g溶解於DMI 14g、2,3-丁二醇4g及二丙二醇單甲醚2g之混合溶劑中,調製電荷輸送性塗料D。
在氮氣氛圍下,將合成例2中合成之寡聚苯胺衍生物B 0.051g、合成例6中合成之苯胺衍生物X 0.129g及芳基磺酸A 0.383g溶解於DMI 6.7g、CHA 10g及PG 3.3g之混合溶劑中,調製電荷輸送性塗料E。
在氮氣氛圍下,將合成例3中合成之寡聚苯胺衍生物C 0.051g、合成例6中合成之苯胺衍生物X 0.129g及芳基磺酸A 0.383g溶解於DMI 6.7g、CHA 10g及PG 3.3g之混合溶劑中,調製電荷輸送性塗料F。
以下之實施例及比較例中,係使用作為ITO基板係使用於表面上以膜厚150nm圖型化ITO之25mm×25mm×0.7t之玻璃基板,於使用前藉O2電漿洗淨裝置(150W,30秒)去除表面上之雜質者。
使用旋轉塗佈器將實施例1-1所得之塗料塗佈於ITO基板後,於大氣下,於80℃燒成1分鐘,其次於230℃正式燒成15分鐘,於ITO基板上形成40nm之薄膜。
使用蒸鍍裝置(真空鍍4.0×10-5Pa)於其上形成鋁膜獲得單層元件。蒸鍍係以蒸鍍速率0.2nm/秒之條件進行。鋁薄膜膜厚為100nm。
又,為防止因空氣中之氧、水等之影響造成之特性劣化,故利用密封基板密封SLD後,評價其特性。密封係藉以下順序進行。
在氧濃度2ppm以下、露點-85℃以下之氮氣氛圍中,將SLD放置在密封基板之間,以接著材(MORESCO(股)製
之MORESCO MOISTURE CUT WB90US(P))貼合密封基板。此時,將捕水劑(DYNIC(股)製,HD-071010W-40)與SLD一起收納於密封基板內。對貼合之密封基板照射UV光(波長365nm,照射量6,000mJ/cm2)後,在80℃下退火處理1小時,使接著材硬化。
除了使用實施例1-2~1-6所得之塗料代替實施例1-1所得之塗料以外,餘與實施例2-1相同之方法製造SLD。
代替實施例1-1所得之塗料而使用聚乙二氧基噻吩-聚苯乙烯磺酸水溶液(H.C.Starck公司製,AI4083),代替於230℃燒成15分鐘而在150℃燒成30分鐘以外,以與實施例2-1同樣方法製作SLD。
使用旋轉塗佈器將實施例1-1所得之塗料塗佈於ITO基板後,在大氣下於80℃燒成1分鐘,其次於230℃正式燒成15分鐘,於ITO基板上形成40nm之薄膜(電洞注入層)。
使用蒸鍍裝置(真空鍍2.0×10-5Pa)於其上依序積層α-NPD及鋁膜,獲得僅電洞元件。蒸鍍係以蒸鍍速率
0.2nm/秒之條件進行。α-NPD及鋁薄膜膜厚分別設為20nm及100nm。
又,為防止因空氣中之氧、水等之影響造成之特性劣化,故利用密封基板密封HOD後,評價其特性。密封係藉與前述同樣方法進行。
除了使用實施例1-2~1-6所得之塗料代替實施例1-1所得之塗料以外,餘與實施例3-1相同之方法製造HOD。
代替實施例1-1所得之塗料而使用聚乙二氧基噻吩-聚苯乙烯磺酸水溶液(H.C.Starck公司製,AI4083),代替於230℃燒成15分鐘而在150℃燒成30分鐘以外,以與實施例3-1同樣方法製作HOD。
針對前述實施例及比較例製作之各SLD及HOD,測定驅動電壓3V之電流密度。結果示於表4。且於同電壓中,一起顯示HOD電流密度相對於SLD電流密度之相對強度。又,該相對強度高時,表示可效率良好地實現對電洞輸送層之電洞供給。
如表4所示可知,使用由本發明之電荷輸送性塗料製作之電洞注入層之元件,HOD電流密度相對於SLD電流密度之相對強度均較高。
使用旋轉塗佈器將實施例1-1所得之塗料塗佈於ITO基板後,於80℃乾燥1分鐘,進而於大氣氛圍下,於230℃燒成15分鐘,於ITO基板上形成40nm之均一薄膜(電洞注入層)。
使用蒸鍍裝置(真空鍍2.0×10-5Pa)於其上積層α-NPD 20nm。此時之蒸鍍速率為0.2nm/秒。其次共蒸鍍CBP與Ir(ppy)3。共蒸鍍係以Ir(ppy)3濃度成為6%之方式控制蒸鍍速率,而積層40nm。其次,依序積層BAlq、氟化鋰及鋁之薄膜,獲得有機EL元件。此時,蒸鍍速率對於BAlq及鋁為0.2nm/秒,對於氟化鋰為0.02nm/秒。BAlq、氟化鋰及鋁之薄膜膜厚分別設為20nm、0.5nm及100nm。
又,為防止因空氣中之氧、水等之影響造成之特性劣化,故利用密封基板密封有機EL元件後,評價其特性。密封係藉與前述同樣方法進行。
除了使用實施例1-2~1-4所得之塗料代替實施例1-1所得之塗料以外,餘與實施例4-1相同之方法製造有機EL元件。
代替實施例1-1所得之塗料而使用聚乙二氧基噻吩-聚苯乙烯磺酸水溶液(H.C.Starck公司製,AI4083),代替於230℃燒成15分鐘而在150℃燒成30分鐘以外,以與實施例4-1同樣方法製作有機EL元件。
針對該等元件,測定亮度5,000cd/m2之電壓、電流密度、電流效率、半衰期(初期亮度5,000cd/m2)。結果示於表5。又,各元件之發光面尺寸之面積為2mm×2mm。
如表5所示,藉由本發明之電荷輸送性塗料,獲得驅動電壓低、半衰期長之有機EL元件。
使用旋轉塗佈器將實施例1-3所得之塗料塗佈於ITO基板後,於80℃乾燥1分鐘,進而於大氣氛圍下,於230℃燒成15分鐘,於ITO基板上形成40nm之均一薄膜(電洞注入層)。
此用旋轉塗佈器於其上塗佈聚[(9,9-二辛基茀-2,7-二基)-共聚-(4,4’-(N-(對-丁基苯基))二苯基胺)](和光純藥工業(股)製)之0.7質量%二甲苯溶液後,於150℃燒成10分鐘,於電洞注入層上形成20nm之均一薄膜(電洞輸送層)。
進而使用蒸鍍裝置(真空鍍2.0×10-5Pa)於其上共蒸鍍CBP與Ir(ppy)3。共蒸鍍係以Ir(ppy)3濃度成為6%之方式控制蒸鍍速率,而積層40nm。其次,依序積層BAlq、氟化鋰及鋁之薄膜,獲得有機EL元件。此時,蒸鍍速率對於BAlq及鋁為0.2nm/秒,對於氟化鋰為0.02nm/秒。BAlq、氟化鋰及鋁之薄膜膜厚分別設為20nm、0.5nm及100nm。
又,為防止因空氣中之氧、水等之影響造成之特性劣化,故利用密封基板密封有機EL元件後,評價其特性。密封係藉與前述同樣方法進行。
除了使用實施例1-5、1-6所得之塗料代替實施例1-3所得之塗料以外,餘與實施例5-1相同之方法製造有機EL元件。
針對該等元件,測定亮度1,000cd/m2之電壓、電流密度、電流效率、半衰期(初期亮度1,000cd/m2)。結果示於表6。又,各元件之發光面尺寸之面積為2mm×2mm。
如表6所示,藉由本發明之電荷輸送性塗料,獲得驅動電壓低、半衰期長之有機EL元件。
Claims (11)
- 一種電荷輸送性塗料,其特徵係含有由以下述式(1)表示之含氟原子之寡聚苯胺衍生物所成之電荷輸送物質、不含氟原子之電荷輸送性物質、及有機溶劑,
- 如請求項1之電荷輸送性塗料,其中A係可經氰基、氯原子、溴原子、碘原子、硝基或碳數1~20之氟烷氧基取代之碳數1~20之氟烷基,可經氰基、氯原子、溴原子、碘原子、硝基、碳數1~20之烷基、碳數1~20之氟烷基或碳數1~20之氟烷氧基取代之碳數6~20之氟芳基,或可經碳數1~20之氟烷基、碳數3~20之氟環烷基、碳數4~20之氟雙環烷基、碳數2~20之氟烯基或碳數2~20之氟炔基取代並且可經氰基、鹵原子或碳數1~20之氟烷氧基取代之碳數6~20之芳基。
- 如請求項2之電荷輸送性塗料,其中A係可經氰基、氯原子、溴原子、碘原子、硝基、碳數1~20之烷基、碳數1~20之氟烷基或碳數1~20之氟烷氧基取代之經3個以上氟原子取代之苯基,或可經碳數3~20之氟環烷基、碳數4~20之氟雙環烷基、碳數2~20之氟烯基或碳數2~20之氟炔基取代並且可經氰基、鹵原子或碳數1~20之氟烷氧基取代之苯基。
- 如請求項1~3中任一項之電荷輸送性塗料,其中R1為氫原子。
- 如請求項1~4中任一項之電荷輸送性塗料,其中R2~R10為氫原子。
- 如請求項1~5中任一項之電荷輸送性塗料,其中k為2~10之整數。
- 如請求項1~6中任一項之電荷輸送性塗料,其中前述不含氟原子之電荷輸送性物質係以下述式(4)表示者:
- 如請求項1~7中任一項之電荷輸送性塗料,其中進而含有摻雜劑。
- 一種電荷輸送性薄膜,其係使用如請求項1~8中任一項之電荷輸送性塗料製作者。
- 一種有機電致發光元件,其具有如請求項9之電荷輸送性薄膜。
- 一種下述式(1)表示之含氟原子之寡聚苯胺衍生物之製造方法,其特徵為使式(2B)表示之胺化合物與以式(3B)或(3B’)表示之含氟原子之化合物在鹼存在下反應:
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