TW201600494A - 苯胺衍生物及其使用 - Google Patents
苯胺衍生物及其使用 Download PDFInfo
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- TW201600494A TW201600494A TW104108132A TW104108132A TW201600494A TW 201600494 A TW201600494 A TW 201600494A TW 104108132 A TW104108132 A TW 104108132A TW 104108132 A TW104108132 A TW 104108132A TW 201600494 A TW201600494 A TW 201600494A
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- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- BJMDYNHSWAKAMX-UHFFFAOYSA-N methyl(diphenyl)sulfanium Chemical compound C=1C=CC=CC=1[S+](C)C1=CC=CC=C1 BJMDYNHSWAKAMX-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 description 1
- GDHRQDYGUDOEIZ-UHFFFAOYSA-N n,n,2-trimethylpropan-1-amine Chemical compound CC(C)CN(C)C GDHRQDYGUDOEIZ-UHFFFAOYSA-N 0.000 description 1
- YPJRZWDWVBNDIW-MBALSZOMSA-N n,n-diphenyl-4-[(e)-2-[4-[4-[(e)-2-[4-(n-phenylanilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]aniline Chemical group C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1/C=C/C(C=C1)=CC=C1C(C=C1)=CC=C1\C=C\C(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 YPJRZWDWVBNDIW-MBALSZOMSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 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
- 239000003208 petroleum Substances 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- RKCAIXNGYQCCAL-UHFFFAOYSA-N porphin Chemical compound N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 RKCAIXNGYQCCAL-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 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
- 150000003839 salts Chemical class 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 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
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 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
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction 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
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 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
- 238000007738 vacuum evaporation 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
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Abstract
例如以下述式所示般的苯胺衍生物,對於有機溶劑之溶解性為良好之同時,將包含該等以作為電荷輸送性物質之薄膜適用於電洞注入層時,可得到具有優異輝度特性的有機EL元件。
□
Description
本發明為關於苯胺衍生物及其使用。
有機電致發光(以下稱為有機EL)元件中,作為發光層或電荷注入層為使用由有機化合物所成的電荷輸送性薄膜。特別是電洞注入層,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重要之機能。
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,與以旋轉塗布法為代表的濕式製程,將該等各製程相比時,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,現今隨著有機EL顯示器的大面積化之進展,期望能以濕式製程來形成電洞注入層。
有鑑於如此般之情事,本發明人已開發一電荷輸送性材料、或使用於其的對於有機溶劑的溶解性為良好的化合物,其係能適用於各種濕式製程之同時,可賦予適用於有機EL元件之電洞注入層時實現優異EL元件特性的薄膜(參考例如專利文獻1~4)。
[先前技術文獻]
[專利文獻]
[專利文獻1]國際公開第2008/067276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
本發明亦與至今已開發的上述專利文獻之技術為相同地以提供一種苯胺衍生物為目的,其係對於有機溶劑為顯示良好溶解性之同時,使其薄膜化並適用於電洞注入層時,可實現具有優異輝度特性的有機EL元件。
本發明人為了達成上述目的經深入研究之結果發現,無法取得醌二亞胺(quinonediimine)構造的指定的苯胺衍生物,係對於有機溶劑具有優異的溶解性,將其溶解至有機溶劑來調製清漆,可自該清漆得到發揮高電荷輸送性的薄膜,以及將該薄膜適用於有機EL元件之電洞注入層時可得到高輝度之元件,因而完成本發明。
即,本發明為提供下述之發明。
<1>.一種苯胺衍生物,其特徵係式(1)所表示,
[式中,R1~R5相互獨立表示氫原子、鹵素原子、硝基、氰基、或可經鹵素原子取代的碳數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;Ph1相互獨立表示式(P1)所表示之基,
(式中,R6~R9相互獨立表示氫原子、鹵素原子、硝基、氰基、或可經鹵素原子取代的碳數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);Ar1相互獨立表示式(A1)~(A14)所表示之任一之基,
;m表示1~5之整數]。
<2>.如前述<1>之苯胺衍生物,其中,前述R1~R9全部為氫原子。
<3>.如前述<1>或<2>之苯胺衍生物,其中,前述Ar1相互獨立為式(A1)~(A12)所表示之任一之基。
<4>.如前述<3>之苯胺衍生物,其中,前述Ar1相互獨立為式(A1)~(A3)、(A5)~(A7)、及(A10)~(A12)所表示之任一之基。
<5>.如前述<1>~<4>中任一項之苯胺衍生物,其中,前述Ar1全部為相同之基。
<6>.一種電荷輸送性物質,其係由前述<1>~<5>中任一項之苯胺衍生物所成。
<7>.一種電荷輸送性材料,其係包含前述<6>之電荷
輸送性物質。
<8>.一種電荷輸送性清漆,其係包含前述<6>之電荷輸送性物質、與有機溶劑。
<9>.如前述<8>之電荷輸送性清漆,其中,進而包含摻雜劑物質。
<10>.如前述<9>之電荷輸送性清漆,其中,前述摻雜劑物質包含鹵代四氰醌二甲烷化合物。
<11>.如前述<10>之電荷輸送性清漆,其中,前述摻雜劑物質進而包含雜多酸。
<12>.一種電荷輸送性薄膜,其係使用前述<8>~<11>中任一項之電荷輸送性清漆而製作。
<13>.一種電子裝置,其係具有前述<12>之電荷輸送性薄膜。
<14>.一種有機電致發光元件,其係具有前述<12>之電荷輸送性薄膜。
<15>.一種電荷輸送性薄膜之製造方法,其特徵係將前述<8>~<11>中任一項之電荷輸送性清漆塗布至基材上並使溶劑蒸發。
<16>.一種前述<1>之苯胺衍生物之製造方法,其特徵係在觸媒存在下,使式(2)所表示之胺化合物與式(3)所表示之芳基化合物反應,
(式中,R1~R5、Ph1、及m表示與前述為相同之意思),【化5】Ar1-Z (3)
(式中,Z表示鹵素原子或擬鹵素基,Ar1表示與前述為相同之意思)。
本發明的苯胺衍生物易溶解於有機溶劑中,將此與摻雜劑(dopant)一起溶解於有機溶劑,可容易地調製電荷輸送性清漆。
由本發明的電荷輸送性清漆而製作的薄膜為展現出高電荷輸送性,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。特以,藉由將此薄膜適用於有機EL元件之電洞注入層,可得到輝度特性為優異的有機EL元件。
又,即使是使用旋轉塗布法或隙縫塗布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。
[實施發明之的最佳形態]
以下,對於本發明更詳細予以說明。
本發明相關的苯胺衍生物為式(1)所表示。
式中,Ph1相互獨立表示式(P1)所表示之基。
上述R1~R9相互獨立表示氫原子、鹵素原子、硝基、氰基、或可經鹵素原子取代的碳數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。
作為鹵素原子,可列舉氟原子、氯原子、溴原子、碘原子等。
作為碳數1~20之烷基,可為直鏈狀、支鏈狀、環狀之任一者,可列舉例如甲基、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2~20之烯基之具體例,可列舉乙烯
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。
作為碳數2~20之炔基之具體例,可列舉乙炔基、n-1-丙炔基、n-2-丙炔基、n-1-丁炔基、n-2-丁炔基、n-3-丁炔基、1-甲基-2-丙炔基、n-1-戊炔基、n-2-戊炔基、n-3-戊炔基、n-4-戊炔基、1-甲基-n-丁炔基、2-甲基-n-丁炔基、3-甲基-n-丁炔基、1,1-二甲基-n-丙炔基、n-1-己炔基、n-1-癸炔基、n-1-十五炔基、n-1-二十炔基等。
作為碳數6~20之芳基之具體例,可列舉苯基、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。
作為碳數2~20之雜芳基之具體例,可列舉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。
此等之中又以R1~R9為氫原子、氟原子、氰基、可經鹵素原子取代的碳數1~20之烷基、可經鹵素原子取代的碳數6~20之芳基、可經鹵素原子取代的碳數2~20之雜芳基為較佳,以氫原子、氟原子、氰基、可經鹵素原子取代的碳數1~10之烷基、可經鹵素原子取代的
苯基為又較佳,以氫原子、氟原子為更佳,以氫原子為最適合。
上述式(1)中的Ar1相互獨立表示式(A1)~(A14)所表示之任一之基。
此等之中又以所謂提升化合物之對於有機溶劑之溶解性、或所得到的薄膜之電荷輸送性之點而言,式(A1)~(A12)所表示之任一之基為較佳,式(A1)~(A3)、(A5)~(A7)、及(A10)~(A12)所表示之任一之基為又較佳,式(A1)、(A5)、及(A10)~(A12)所表示之任一之基為更佳,式(A1)及(A5)所表示之任一之基為又更佳。
上述式(1)中的m表示1~5之整數,但以提高化合物之對於有機溶劑之溶解性之點而言,以4以下為較
佳,以3以下為又較佳,以提高電荷輸送性之點而言,以2以上為較佳,以3以上為又較佳。
尚,在本發明中,上述烷基、烯基及炔基之碳數,較佳為10以下,又較佳為6以下,更佳為4以下。
又,芳基及雜芳基之碳數,較佳為14以下,又較佳為10以下,更佳為6以下。
在上述式(1)中,以Ar1全部為相同之基為較佳,以Ph1全部為相同之基為較佳。
本發明的式(1)所示的苯胺衍生物,其係可在觸媒存在下,使式(2)所表示之胺化合物與式(3)所表示之芳基化合物反應而製造。
(式中,Z表示鹵素原子或擬鹵素基,R1~R5、Ar1、Ph1、及m表示與前述為相同之意思)。
作為鹵素原子,可列舉與上述為相同者。
作為擬鹵素基,可列舉甲磺醯氧基(methanesulfonyloxy)、三氟甲磺醯氧基、九氟丁磺醯氧基等之(氟)烷基磺醯氧基;苯磺醯氧基(benzenesulfonyloxy)、甲苯磺醯氧基等之芳香族磺醯氧基等。
式(2)所表示之胺化合物與式(3)所表示之芳基
化合物之置入比,相對於胺化合物之全NH基之物質量,可將芳基化合物設為當量以上,但以1~1.2當量左右為合適。
作為使用於上述反應的觸媒,可列舉例如氯化銅、溴化銅、碘化銅等之銅觸媒;Pd(PPh3)4(肆(三苯基膦)鈀)、Pd(PPh3)2Cl2(雙(三苯基膦)二氯鈀)、Pd(dba)2(雙(亞苄基丙酮)鈀)、Pd2(dba)3(參(亞苄基丙酮)二鈀)、Pd(P-t-Bu3)2(雙(三t-丁基膦)鈀)等之鈀觸媒等。此等觸媒可單獨使用亦可組合2種以上使用。又,此等觸媒亦可同時與周知適當的配位子使用。
觸媒之使用量,相對於式(3)所表示之芳基化合物1mol,可設為0.2mol左右,以0.15mol左右為合適。
又,使用配位子時,該使用量相對於使用的金屬錯合體而言,可設為0.1~5當量,以1~2當量為合適。
上述各反應亦可在溶劑中進行。使用溶劑時,該種類只要是不會對於反應造成不良影響者即可,未特別限制。作為具體例,可列舉脂肪族烴類(戊烷、n-己烷、n-辛烷、n-癸烷、十氫萘等)、鹵素化脂肪族烴類(三氯甲烷、二氯甲烷、二氯乙烷、四氯化碳等)、芳香族烴類(苯、硝基苯、甲苯、o-二甲苯、m-二甲苯、p-二甲苯、均三甲苯等)、鹵素化芳香族烴類(氯苯、溴苯、o-二氯苯、m-二氯苯、p-二氯苯等)、醚類(二乙基醚、二異丙基醚、t-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、甲基異丁酮、二-n-丁酮、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-二甲基咪唑啉酮、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,此等溶劑可單獨使用,亦可混合2種以上使用。
反應溫度係適宜設定在所使用之溶劑之融點至沸點為止之範圍內即可,特以0~200℃左右為較佳,以20~150℃為又較佳。
反應結束後,依據常法進行後處理,而可得到目的之胺衍生物。
以下為舉例式(1)所表示之苯胺衍生物之具體例,但不限定於此。
本發明的電荷輸送性清漆,其係包含由式(1)所表示之苯胺衍生物所成的電荷輸送性物質、與有機溶劑,但因應所得到的薄膜之用途,以提升該電荷輸送能之目的,亦可包含摻雜劑物質。
作為摻雜劑物質,只要是可溶解於清漆中使用之至少1種溶劑中者,未特別限定,可使用無機系之摻雜劑物質、有機系之摻雜劑物質之任一者。
特以,作為無機系之摻雜劑物質,以雜多酸(heteropolyacid)為較佳。
所謂的雜多酸,代表性為式(D1)所示的Keggin型或式(D2)所示的Dawson型之化學構造所表示,具有雜原子位於分子中心之構造,且為釩(V)、鉬(Mo)、鎢(W)等含氧酸之異多酸與異種元素之含氧酸縮合而成之多元酸。作為如此般的異種元素之含氧酸,列舉主要為矽(Si)、磷(P)、砷(As)之含氧酸。
作為雜多酸之具體例,可列舉磷鉬酸、矽鉬酸、磷鎢酸、矽鎢酸、磷鎢鉬酸等,該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,可為以市售品所取得者,又,亦可為藉由周知方法所合成者。
特以,使用1種類的雜多酸時,該1種類的雜多酸以磷鎢酸或磷鉬酸為較佳,以磷鎢酸為最適合。又,使用2種類以上的雜多酸時,該2種類以上的雜多酸之1個,以磷鎢酸或磷鉬酸為較佳,以磷鎢酸為又較佳。
尚,本發明中可使用的雜多元酸可為,無論是元素分
析等之定量分析中來自一般式所表示的構造之元素數量為較多之物或較少之物,其可由市售品取得之物,或依據周知之合成方法適當合成之物。
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分別來表示,本發明可使用無論定量分析中該式中的P(磷)、O(氧)、W(鎢)或Mo(鉬)數量為較多之物或較少之物,其可由市售品取得之物,或依據周知之合成方法適當合成之物。此時本發明中所規定的雜多元酸之質量係指,不為合成物或市售品中純粹的磷鎢酸之質量(磷鎢酸含量),而係可取得之市售品形態及周知之合成法中可單離之形態中,含有水合水及其他雜質等之狀態下的全質量。
本發明的電荷輸送性清漆中所包含的雜多酸,以質量比計,相對於由本發明的苯胺衍生物所成的電荷輸送性物質1,可設為0.01~50左右,較佳為0.1~10左右,又較佳為1.0~5.0左右。
另一方面,作為有機系之摻雜劑物質,特以四氰醌二甲烷衍生物或苯醌衍生物為較佳。
作為四氰醌二甲烷衍生物之具體例,可列舉7,7,8,8-四氰醌二甲烷(TCNQ)、或式(4)所表示之鹵代四氰醌二甲烷等。
又,作為苯醌衍生物之具體例,可列舉四氟-1,4-苯醌(F4BQ)、四氯-1,4-苯醌(氯冉酸)、四溴-1,4-苯醌、2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ)等。
式中,R10~R13相互獨立表示氫原子或鹵素原子,但至少1個為鹵素原子,至少2個為鹵素原子為較佳,至少3個為鹵素原子為又較佳,全部為鹵素原子為最佳。
作為鹵素原子,可列舉與上述為相同者,以氟原子或氯原子為較佳,以氟原子為又較佳。
作為鹵代四氰醌二甲烷化合物之具體例,可列舉2-氟-7,7,8,8-四氰醌二甲烷、2-氯-7,7,8,8-四氰醌二甲烷、2,5-二氟-7,7,8,8-四氰醌二甲烷、2,5-二氯-7,7,8,8-四氰醌二甲烷、2,3,5,6-四氯-7,7,8,8-四氰醌二甲烷、2,3,5,6-四氟-7,7,8,8-四氰醌二甲烷(F4TCNQ)等,本發明中以F4TCNQ為最適合。
本發明的電荷輸送性清漆中的四氰醌二甲烷衍生物及苯醌衍生物之含有量,相對於本發明的苯胺衍生物,較佳為0.0001~50當量,又較佳為0.001~20當量,又更佳為0.01~10當量。
本發明中,若考量可再現性良好地得到高電荷輸送性薄膜、摻雜劑物質之易取得性等時,作為摻雜劑物質,較佳為包含鹵代四氰醌二甲烷及苯醌衍生物之至少1種,又較佳為包含F4TCNQ及DDQ之至少1種。
又,將所得到的薄膜使用作為有機EL元件之電洞注入層之情形,若考量可再現性良好地得到高壽命元件、摻雜劑物質之易取得性等時,作為摻雜劑物質,較佳為包含鹵代四氰醌二甲烷及苯醌衍生物之至少1種與雜多酸,又較佳為包含鹵代四氰醌二甲烷及苯醌衍生物之至少1種與磷鎢酸及磷鉬酸之至少1種,更佳為包含F4TCNQ及DDQ之至少1種與磷鎢酸。
更,將所得到的薄膜使用作為有機EL元件之電洞注入層之情形,若考量可再現性良好地得到高壽命元件時,本發明的電荷輸送性清漆較佳為包含有機矽烷化合物。
作為有機矽烷化合物,可列舉二烷氧基矽烷化合物、三烷氧基矽烷化合物或四烷氧基矽烷化合物,該等可單獨使用,亦可組合2種以上使用。
尤以,作為有機矽烷化合物,以二烷氧基矽烷化合物或三烷氧基矽烷化合物為較佳,以三烷氧基矽烷化合物為又較佳。
作為該等烷氧基矽烷化合物,可列舉例如式(5)~(7)所示者。
Si(OR)4 (5)
SiR'(OR)3 (6)
Si(R')2(OR)2 (7)
式中,R相互獨立表示可經Z1所取代的碳數1~20之烷基、可經Z1所取代的碳數2~20之烯基、可經Z1所取代的碳數2~20之炔基、可經Z2所取代的碳數
6~20之芳基、或可經Z2所取代的碳數2~20之雜芳基;R’相互獨立表示可經Z3所取代的碳數1~20之烷基、可經Z3所取代的碳數2~20之烯基、可經Z3所取代的碳數2~20之炔基、可經Z4所取代的碳數6~20之芳基、或可經Z4所取代的碳數2~20之雜芳基。
Z1表示為鹵素原子、可經Z5所取代的碳數6~20之芳基、或可經Z5所取代的碳數2~20之雜芳基;Z2表示為鹵素原子、可經Z5所取代的碳數1~20之烷基、可經Z5所取代的碳數2~20之烯基、或可經Z5所取代的碳數2~20之炔基。
Z3表示為鹵素原子、可經Z5所取代的碳數6~20之芳基、可經Z5所取代的碳數2~20之雜芳基、環氧環己基、縮水甘油氧基、甲基丙烯醯氧基、丙烯醯氧基、脲基(-NHCONH2)、硫醇基、異氰酸酯基(-NCO)、胺基、-NHY1基、或-NY2Y3基;Z4表示為鹵素原子、可經Z5所取代的碳數1~20之烷基、可經Z5所取代的碳數2~20之烯基、可經Z5所取代的碳數2~20之炔基、環氧環己基、縮水甘油氧基、甲基丙烯醯氧基、丙烯醯氧基、脲基(-NHCONH2)、硫醇基、異氰酸酯基(-NCO)、胺基、-NHY1基、或-NY2Y3基;Y1~Y3相互獨立表示可經Z5所取代的碳數1~20之烷基、可經Z5所取代的碳數2~20之烯基、可經Z5所取代的碳數2~20之炔基、可經Z5所取代的碳數6~20之芳基、或可經Z5所取代的碳數2~20之雜芳基。
Z5表示為鹵素原子、胺基、硝基、氰基或硫醇基。
式(5)~(7)中,作為鹵素原子、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,可列舉與上述為相同者。
R及R’中,烷基、烯基及炔基之碳數,較佳為10以下,又較佳為6以下,更佳為4以下。
又,芳基及雜芳基之碳數,較佳為14以下,又較佳為10以下,更佳為6以下。
作為R,較佳為可經Z1所取代的碳數1~20之烷基或碳數2~20之烯基、或可經Z2所取代的碳數6~20之芳基;又較佳為可經Z1所取代的碳數1~6之烷基或碳數2~6之烯基、或可經Z2所取代的苯基;更佳為可經Z2所取代的碳數1~4之烷基或可經Z2所取代的苯基;又更佳為可經Z1所取代的甲基或乙基。
又,作為R’,較佳為可經Z3所取代的碳數1~20之烷基或可經Z4所取代的碳數6~20之芳基;又較佳為可經Z3所取代的碳數1~10之烷基或可經Z4所取代的碳數6~14之芳基;更佳為可經Z3所取代的碳數1~6之烷基、或可經Z4所取代的碳數6~10之芳基;又更佳為可經Z3所取代的碳數1~4之烷基或可經Z4所取代的苯基。
尚,複數個R可全部為相同亦可為相異;複數個R’亦可全部為相同或相異。
作為Z1,較佳為鹵素原子或可經Z5所取代的碳數6~20之芳基;又較佳為氟原子或可經Z5所取代的苯基;以不存在(即,非取代)為最適合。
又,作為Z2,較佳為鹵素原子或可經Z5所取代的碳數6~20之烷基;又較佳為氟原子或可經Z5所取代的碳數1~10烷基;以不存在(即,非取代)為最適合。
另一方面,作為Z3,較佳為鹵素原子、可經Z5所取代的苯基、可經Z5所取代的呋喃基、環氧環己基、縮水甘油氧基、甲基丙烯醯氧基、丙烯醯氧基、脲基、硫醇基、異氰酸酯基、胺基、可經Z5所取代的苯基胺基、或可經Z5所取代的二苯基胺基;又較佳為鹵素原子;更佳為氟原子、或不存在(即,非取代)。
又,作為Z4,較佳為鹵素原子、可經Z5所取代的碳數1~20之烷基、可經Z5所取代的呋喃基、環氧環己基、縮水甘油氧基、甲基丙烯醯氧基、丙烯醯氧基、脲基、硫醇基、異氰酸酯基、胺基、可經Z5所取代的苯基胺基、或可經Z5所取代的二苯基胺基;又較佳為鹵素原子;更佳為氟原子、或不存在(即,非取代)。
又,作為Z5較佳為鹵素原子;又較佳為氟原子或不存在(即,非取代)。
以下為舉例可在本發明使用的有機矽烷化合物之具體例,但並不限定於此等。
作為二烷氧基矽烷化合物之具體例,列舉如:二甲基二甲氧基矽烷、二甲基二乙氧基矽烷、甲基乙基二甲氧基矽烷、二乙基二甲氧基矽烷、二乙基二乙氧基矽烷、甲基丙基二甲氧基矽烷、甲基丙基二乙氧基矽烷、二異丙基二甲氧基矽烷、苯基甲基二甲氧基矽烷、乙烯基甲基二甲氧
基矽烷、3-縮水甘油氧基丙基甲基二甲氧基矽烷、3-縮水甘油氧基丙基甲基二乙氧基矽烷、3-(3,4-環氧環己基)乙基甲基二甲氧基矽烷、3-甲基丙烯醯氧基丙基甲基二甲氧基矽烷、3-甲基丙烯醯氧基丙基甲基二乙氧基矽烷、3-巰基丙基甲基二甲氧基矽烷、γ-胺基丙基甲基二乙氧基矽烷、N-(2-胺基乙基)胺基丙基甲基二甲氧基矽烷、3,3,3-三氟丙基甲基二甲氧基矽烷等。
作為三烷氧基矽烷化合物之具體例,列舉如:甲基三甲氧基矽烷、甲基三乙氧基矽烷、乙基三甲氧基矽烷、乙基三乙氧基矽烷、丙基三甲氧基矽烷、丙基三乙氧基矽烷、丁基三甲氧基矽烷、丁基三乙氧基矽烷、戊基三甲氧基矽烷、戊基三乙氧基矽烷、庚基三甲氧基矽烷、庚基三乙氧基矽烷、辛基三甲氧基矽烷、辛基三乙氧基矽烷、月桂基三甲氧基矽烷、月桂基三乙氧基矽烷、十六基三甲氧基矽烷、十六基三乙氧基矽烷、十八基三甲氧基矽烷、十八基三乙氧基矽烷、苯基三甲氧基矽烷、苯基三乙氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、3-胺基丙基三甲氧基矽烷、3-胺基丙基三乙氧基矽烷、3-縮水甘油氧丙基三甲氧基矽烷、3-縮水甘油氧丙基三乙氧基矽烷、3-甲基丙烯醯氧基丙基三甲氧基矽烷、3-甲基丙烯醯氧基丙基三乙氧基矽烷、三乙氧基(4-(三氟甲基)苯基)矽烷、月桂基三乙氧基矽烷、3,3,3-三氟丙基三甲氧基矽烷、(三乙氧基矽烷基)環己烷、全氟辛基乙基三乙氧基矽烷、三乙氧基氟矽烷、十三氟-1,1,2,2-四氫辛基三乙氧
基矽烷、五氟苯基三甲氧基矽烷、五氟苯基三乙氧基矽烷、3-(七氟異丙氧基)丙基三乙氧基矽烷、十七氟-1,1,2,2-四氫癸基三乙氧基矽烷、三乙氧基-2-噻吩基矽烷、3-(三乙氧基矽烷基)呋喃等。
作為四烷氧基矽烷化合物之具體例,列舉如:四乙氧基矽烷、四甲氧基矽烷、四丙氧基矽烷等。
此等之中又以3,3,3-三氟丙基甲基二甲氧基矽烷、三乙氧基(4-(三氟甲基)苯基)矽烷、3,3,3-三氟丙基三甲氧基矽烷、全氟辛基乙基三乙氧基矽烷、五氟苯基三甲氧基矽烷、五氟苯基三乙氧基矽烷為較佳。
若本發明的電荷輸送性清漆含有有機矽烷化合物時,相對於電荷輸送性物質(包含摻雜劑物質時為電荷輸送性物質及摻雜劑物質)之總質量,有機矽烷化合物之含有量通常為0.1~50質量%左右,但考量抑制所得到的薄膜的電荷輸送性之降低,且能提高對於如上述般將電洞注入層以相接於陰極側之方式所層合之層之電洞注入能時,較佳為0.5~40質量%左右,又較佳為0.8~30質量%左右,更佳為1~20質量%左右。
尚,本發明的電荷輸送性清漆中,除了由上述苯胺衍生物所成的電荷輸送性物質以外,亦可使用其他周知的電荷輸送性物質。
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,N-二甲基異丁醯胺、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之有機溶劑,但不限定於該等。此等溶劑可單獨使用1種,或混合2種以上使用,該使用量,相對於使用於清漆的全體溶劑,可設為5~100質量%。
尚,電荷輸送性物質及摻雜劑物質,較佳為皆能完全溶解於上述溶劑中,或可成為均勻分散之狀態,以能完全溶解為又較佳。
又,本發明中,藉由使清漆中含有至少1種類的高黏度有機溶劑(於25℃時具有10~200mPa‧s,特以35~150mPa‧s之黏度,且常壓(大氣壓)下沸點為50~300℃,特以150~250℃),清漆之黏度調整將變得容易,其結果,清漆之調製可成為能因應所使用的塗布方法而再現性良好地賦予平坦性為高的薄膜。
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。此等溶劑可單獨使用,或混合2種以上使用。
相對於使用於本發明的清漆的全體溶劑,該高黏度有機溶劑之添加比例以固體不會析出之範圍內為較佳,只要固體為不會析出,該添加比例較佳為5~80質量%。
更,為了提升對於基板之濕潤性、溶劑之表
面張力之調整、極性之調整、沸點之調整等之目的,相對於使用於清漆的全體溶劑,亦可以1~90質量%(較佳為1~50質量%)之比例來混合其他溶劑。
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-乙酸己酯等,但不限定於該等。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,但通常在25℃為1~50mPa‧s。
又,本發明中的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,就考量提升清漆之塗布性時,較佳為0.5~5.0質量%左右,又較佳為1.0~3.0質量%左右。
作為電荷輸送性清漆之調製法未特別限定,可列舉例如:將本發明的苯胺衍生物溶解於高溶解性溶劑中,再對此添加高黏度有機溶劑之方法;或,將高溶解性溶劑與高黏度有機溶劑混合,再對此使本發明的苯胺衍生物溶解之方法。
本發明中,電荷輸送性清漆,以再現性良好
地得到平坦性為更高的薄膜之觀點而言,在將電荷輸送性物質、摻雜劑物質等溶解於有機溶劑中後,以使用亞微米級的過濾器等來進行過濾為宜。
藉由將以上所說明的電荷輸送性清漆塗布至基材上並燒成,可使電荷輸送性薄膜形成於基材上。
作為清漆之塗布方法未特別限定,可列舉:浸漬法、旋轉塗布法、轉印印刷法、輥塗法、刷塗法、噴墨法、噴霧法、隙縫塗布法等,較佳為因應塗布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,燒成環境未特別限定,不僅是大氣環境,即使是在氮等之惰性氣體或真空中,亦可得到具有均勻成膜面及電荷輸送性的薄膜,但考量再現性良好地得到高電荷輸送性薄膜時,以大氣環境為較佳。
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,係以在100~260℃左右之範圍內予以適當設定者,但將所得到的薄膜作為有機EL元件之電洞注入層使用時,以140~250℃左右為較佳,以145~240℃左右為又較佳。
尚,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,以5~200nm為較佳。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、或使塗布時基板上的溶液量變化之方法等。
本發明的電荷輸送性薄膜,在有機EL元件中,可適合使用作為電洞注入層,亦可使用作為電洞注入輸送層等之電荷輸送性機能層。
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,於陽極基板上塗布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。將此導入至真空蒸鍍裝置內,依序蒸鍍電洞輸送層、發光層、電子輸送層、電子輸送層/電洞阻擋層、陰極金屬而製成OLED元件。尚,因應所需,發光層與電洞輸送層之間設置電子阻擋層。
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,或由以鋁所代表之金屬或該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金屬,可舉出鈧、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,但並不限定於此等。
作為形成電洞輸送層之材料,列舉如:(三苯基胺)二聚物衍生物、[(三苯基胺)二聚物]螺二聚物、N,N’-雙(萘基-1-基)-N,N’-雙(苯基)-聯苯胺(α-NPD)、N,N’-雙(萘基-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(萘基-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-芴、N,N’-雙(萘基-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(萘基-1-基)-N,N’-雙(苯基)-9,9-二苯基-芴、N,N’-雙(萘基-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、9,9-雙[4-(N,N-雙-聯苯-4-基-胺基)苯基]-9H-芴、9,9-雙[4-(N,N-雙-萘基-2-基-胺基)苯基]-9H-芴、9,9-雙[4-(N-萘基-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-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-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-萘基-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(萘基-2-基)-聯苯胺、N,N,N’,N’-四(萘基)-聯苯胺、N,N’-二(萘基-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,N6-四苯基萘基-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)等之低聚物噻吩類等。
作為形成發光層之材料,列舉如: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-苯基酚根)鋁(III)(BAlq)、4,4’-雙(2,2-二苯基乙烯基)聯苯、9,10-二(萘基-2-基)蒽、2-t-丁基-9,10-二(萘基-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(萘基-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)-芴-2-基]-9,9-二(4-甲基苯基)芴、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-芴、2,2’-雙(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-4-基)稠五苯、3,9-二(萘基-2-基)苝、3,10-二(萘基-2-基)苝、參[4-(芘基)-苯基]胺、10,10’-二(聯苯-4-基)-9,9’-聯蒽、N,N’-二(萘基-1-基)-N,N’-二苯基-[1,1’:4’,1”:4”,1'''-四聯苯]-4,4'''-二胺、4,4’-二[10-(萘基-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-芴-2-基)芘、1-(7-(9,9’-聯蒽-10-基)-9,9-二己烷基-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-旋環雙芴、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-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-苯并[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-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-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進行共蒸鍍而形成發光層。
作為發光性摻雜劑,列舉如:3-(2-苯并噻唑基)-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-苯并噻唑基)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)(乙醯丙酮酸鹽)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)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]二苯乙烯基、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(萘基-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-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)萘基-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-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-二苯基萘基-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-甲基苯并咪唑鎓)(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)-6-三甲苯基-N-(6-三甲苯基喹啉-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-吡喃-4-亞基)丙二腈、4-(二氰基亞甲基)-2-甲基-6-朱咯啶基-9-烯基-4H-吡喃、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-吡喃、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-吡喃、參(二苯甲醯基甲烷)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)(乙醯丙酮酸鹽)銥(III)、參(1-苯基異喹啉)銥(III)、雙(1-苯基異喹啉)(乙醯丙酮酸鹽)銥(III)、雙[1-(9,9-二甲基-9H-芴-2-基)-異喹啉](乙醯丙酮酸鹽)銥(III)、雙[2-(9,9-二甲基-9H-芴-2-基)喹啉](乙醯丙酮酸鹽)銥(III)、參[4,4’-二-t-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)(乙醯丙酮酸鹽)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)(乙醯丙酮酸鹽)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](乙醯丙酮酸鹽)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-芴-2-基)-1-苯基-1H-苯并[d]異吡唑根)(乙醯丙酮酸鹽)銥(III)、雙(2-苯基吡啶)(3-(吡啶-2-基)-2H-苯并哌喃-2-酮鹽)銥(III)、雙(2-苯基喹啉)(2,2,6,6-四甲基庚烷-3,5-二酮鹽)銥(III)、雙(苯基異喹啉)(2,2,6,6-四甲基庚烷-3,5-二酮鹽)銥(III)、銥(III)雙(4-苯基噻吩并[3,2-c]吡啶-N,C2’)乙醯丙酮酸鹽、(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-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](乙醯丙酮酸鹽)銥(III)、白金(II)八乙基卟吩、雙(2-甲基二苯并[f,h]喹啉)(乙醯丙酮酸鹽)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/電洞阻擋層之材料,列舉如:8-羥基喹啉酸鹽-鋰、2,2’,2”-(1,3,5-石油醚甲苯基)-參(1-苯基-1-H-苯并咪唑)、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-喹啉酸鹽)-4-(苯基酚根)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-t-丁基苯基-1,2,4-三唑、4-(萘基-1-基)-3,5-二苯基-4H-1,2,4-三唑、2,9-雙(萘基-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-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、參(2,4,6-三甲基-3-(吡啶-3-基)苯基)硼烷、1-甲基-2-(4-(萘基-2-基)苯基)-1H-咪唑并[4,5f][1,10]啡啉、2-(萘基-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-羥基苯并[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,列舉如: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、苯甲酸鋰等。
作為陰極材料,列舉如:鋁、鎂-銀合金、鋁-鋰合金、鋰、鈉、鉀、銫等。
作為形成電子阻擋層之材料,列舉如:參(苯基吡唑)銥等。
使用本發明的電荷輸送性清漆的PLED元件之製作方法並無特別限定,可列舉以下之方法。
在上述OLED元件製作中,藉由依序形成電洞輸送性高分子層、發光性高分子層,來取代進行電洞輸送層、發光層、電子輸送層、電子注入層之真空蒸鍍操作,可製作具有藉由本發明的電荷輸送性清漆所形成的電荷輸送性薄
膜的PLED元件。
具體而言,於陽極基板上塗布本發明的電荷輸送性清漆並藉由上述方法來製作電洞注入層,再於其上方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。
作為所使用的陰極及陽極材料,可使用與上述OLED元件製作時為相同者,並可進行相同的洗淨處理、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,舉例如在電洞輸送性高分子材料或發光性高分子材料、或該等中為添加有摻雜劑物質的材料之中添加溶劑,使其溶解或均勻分散,塗布至電洞注入層或電洞輸送性高分子層之上方後,藉由分別燒成來進行成膜之方法。
作為電洞輸送性高分子材料,列舉如:聚[(9,9-二己基茀基-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,4-二胺基伸苯基)]、聚[(9,9-二辛基茀基-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,1’-伸聯苯-4,4-二胺)]、聚[(9,9-雙{1’-戊烯-5’-基}茀基-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[(9,9-貳二辛基茀基-2,7-二基)-co-(4,4’-(N-(p-丁基苯基))二苯胺)]等。
作為發光性高分子材料,列舉如:聚(9,9-二烷基芴)(PDAF)等之聚芴衍生物、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。
作為塗布方法未特別限定者,可舉出如噴墨法、噴霧法、浸漬法、旋轉塗布法、轉印印刷法、輥塗法、刷塗法等。尚且,塗布係以在氮、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。
尚,由上述說明的電荷輸送性清漆所得到的電荷輸送性薄膜為具有優異的電荷輸送性,不僅如此連由本發明的苯胺衍生物所得到的蒸鍍膜亦具有優異的電荷輸送性,故依用途而異,亦可使用藉由蒸鍍法所得到的電荷輸送性薄膜。
[實施例]
以下,例舉製造例及實施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)1H-NMR:日本電子(股)製JNM-ECP300 FT NMR SYSTEM
(2)MALDI-TOF-MS:Bruker公司製、autoflex III smartbeam
(3)基板洗淨:長州產業(股)製基板洗淨裝置(減壓電漿方式)
(4)清漆之塗布:Mikasa(股)製旋轉塗布機MS-A100
(5)膜厚測定:(股)小坂研究所製微細形狀測量機Surfcorder ET-4000
(6)EL元件之製作:長州產業(股)製多機能蒸鍍裝置系統C-E2L1G1-N
(7)EL元件之輝度等之測定:(有)Tech World製I-V-L測定系統
[1]化合物之合成
[製造例1]苯胺衍生物1之合成
將四苯胺1.50g、4-溴三苯基胺6.92g、Pd(dba)2118mg、及t-丁氧基鈉2.48g置入於反應容器中,將容器內以氮取代後,加入甲苯35mL、及另外預先準備的三-t-丁基膦之甲苯溶液1.4mL(濃度:59g/L),以50℃攪拌24小時。冷卻至室溫後,添加甲苯及飽和食鹽水來進行分液。將有機層以無水硫酸鈉乾燥後,進行矽凝膠過濾,於所得到的濾液中添加活性碳0.3g並於室溫下攪拌1
小時。將活性碳以過濾予以除去,並濃縮濾液。將濃縮液滴下至由乙酸乙酯300mL及甲醇300mL所成的混合溶劑中,並將生成的漿料液過濾。將所得到的粉末乾燥後,使其再次溶解於1,4-二噁烷約100mL中,滴下至甲醇500mL中,並將生成的漿料液過濾。將所得到的粉末乾燥,而得到作為目的之苯胺衍生物1(4.90g,收率76%)。
1H-NMR(300MHz,THF-d8)δ[ppm]:7.17-7.22(m,20H),6.90-7.06(m,57H).
MALDI-TOF-MS m/Z found:1582.47([M]+calcd:1581.71).
[2]電荷輸送性清漆之調製
[實施例1]
將電荷輸送性物質的苯胺衍生物10.108g、摻雜劑物質的磷鎢酸(PTA)0.202g及四氟四氰醌二甲烷(F4TCNQ)0.094g溶解於1,3-二甲基-2-咪唑啉酮(DMI)14.0g中。於此中添加2,3-丁二醇4.0g及丙二醇單甲基醚(PGME)2.0g並予以攪拌,進而再於此中添加3,3,3-三氟丙基三甲氧基矽烷(信越化學工業(股)製)0.007g及苯基三甲氧基矽烷(信越化學工業(股)製)0.013g並予以攪拌,來調製電荷輸送性清漆。
[3]有機EL元件之製造及特性評價
[實施例2]
使用旋轉塗布機將以實施例1所得到的清漆塗布至ITO基板後,以80℃乾燥1分鐘,進而在大氣環境下,以150℃燒成5分鐘,而在ITO基板上形成30nm的均勻薄膜。作為ITO基板,係使用於表面上銦錫氧化物(ITO)圖型化成膜厚150nm的25mm×25mm×0.7t的玻璃基板,且在使用前藉由O2電漿洗淨裝置(150W、30秒鐘)去除表面上之雜質。
接著,使用蒸鍍裝置(真空度1.0×10-5Pa),對於形成有薄膜之ITO基板上以0.2nm/秒來成膜30nm的α-NPD。接下來,共蒸鍍CBP與Ir(PPy)3。共蒸鍍為以Ir(PPy)3之濃度成為6%之方式來控制蒸鍍速率,並層合40nm。接著,依序層合BAlq、氟化鋰及鋁之薄膜,得到有機EL元件。此時,蒸鍍速率方面,關於BAlq及鋁為以0.2nm/秒、關於氟化鋰為以0.02nm/秒之條件來分別進行,分別使膜厚成為20nm、0.5nm及120nm。
尚,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。對於已貼合的密封基板,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。
對於已製作的元件,測定驅動電流0.7mA中的驅動電壓、輝度及發光效率。結果如表1中所示。尚,各元件之發光面尺寸之面積為2mm×2mm。
如表1所示可得知般,具有將由本發明的電荷輸送性清漆所得到的電荷輸送性薄膜作為電洞注入層的有機EL元件,輝度特性為優異。
Claims (16)
- 一種苯胺衍生物,其特徵係式(1)所表示,
- 如請求項1之苯胺衍生物,其中,前述R1~R9全部為氫原子。
- 如請求項1或2之苯胺衍生物,其中,前述Ar1相互獨立為式(A1)~(A12)所表示之任一之基。
- 如請求項3之苯胺衍生物,其中,前述Ar1相互獨立為式(A1)~(A3)、(A5)~(A7)、及(A10)~(A12)所表示之任一之基。
- 如請求項1~4中任一項之苯胺衍生物,其中,前述Ar1全部為相同之基。
- 一種電荷輸送性物質,其係由請求項1~5中任一項之苯胺衍生物所成。
- 一種電荷輸送性材料,其係包含請求項6之電荷輸送性物質。
- 一種電荷輸送性清漆,其係包含請求項6之電荷輸送性物質、與有機溶劑。
- 如請求項8之電荷輸送性清漆,其中,進而包含摻雜劑物質。
- 如請求項9之電荷輸送性清漆,其中,前述摻雜劑物質包含鹵代四氰醌二甲烷化合物。
- 如請求項10之電荷輸送性清漆,其中,前述摻雜劑物質進而包含雜多酸。
- 一種電荷輸送性薄膜,其係使用請求項8~11中任一項之電荷輸送性清漆而製作。
- 一種電子裝置,其係具有請求項12之電荷輸送性薄膜。
- 一種有機電致發光元件,其係具有請求項12之電荷輸送性薄膜。
- 一種電荷輸送性薄膜之製造方法,其特徵係將請求項8~11中任一項之電荷輸送性清漆塗布至基材上並使溶劑蒸發。
- 一種請求項1之苯胺衍生物之製造方法,其特徵係在觸媒存在下,使式(2)所表示之胺化合物與式(3)所表示之芳基化合物反應,
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