TWI680116B - 電荷傳輸性塗料、電荷傳輸性薄膜及有機電致發光元件 - Google Patents
電荷傳輸性塗料、電荷傳輸性薄膜及有機電致發光元件 Download PDFInfo
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- TWI680116B TWI680116B TW105101869A TW105101869A TWI680116B TW I680116 B TWI680116 B TW I680116B TW 105101869 A TW105101869 A TW 105101869A TW 105101869 A TW105101869 A TW 105101869A TW I680116 B TWI680116 B TW I680116B
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- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000734 polysilsesquioxane polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- KIWATKANDHUUOB-UHFFFAOYSA-N propan-2-yl 2-hydroxypropanoate Chemical compound CC(C)OC(=O)C(C)O KIWATKANDHUUOB-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-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
- MCSINKKTEDDPNK-UHFFFAOYSA-N propyl propionate Chemical compound CCCOC(=O)CC MCSINKKTEDDPNK-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
- 238000010992 reflux Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- QJHDFBAAFGELLO-UHFFFAOYSA-N sec-butyl butyrate Chemical compound CCCC(=O)OC(C)CC QJHDFBAAFGELLO-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 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
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 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
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- IXXMVXXFAJGOQO-UHFFFAOYSA-N tert-butyl 2-hydroxypropanoate Chemical compound CC(O)C(=O)OC(C)(C)C IXXMVXXFAJGOQO-UHFFFAOYSA-N 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- TWBUVVYSQBFVGZ-UHFFFAOYSA-N tert-butyl butanoate Chemical compound CCCC(=O)OC(C)(C)C TWBUVVYSQBFVGZ-UHFFFAOYSA-N 0.000 description 1
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 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 class COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- XSVXWCZFSFKRDO-UHFFFAOYSA-N triphenyl-(3-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=C(C=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XSVXWCZFSFKRDO-UHFFFAOYSA-N 0.000 description 1
- DETFWTCLAIIJRZ-UHFFFAOYSA-N triphenyl-(4-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DETFWTCLAIIJRZ-UHFFFAOYSA-N 0.000 description 1
- LNQMQGXHWZCRFZ-UHFFFAOYSA-N triphenyl-[4-(4-triphenylsilylphenyl)phenyl]silane Chemical group C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 LNQMQGXHWZCRFZ-UHFFFAOYSA-N 0.000 description 1
- HITRWHKLCHWBNZ-UHFFFAOYSA-N triphenyl-[4-(9-phenylfluoren-9-yl)phenyl]silane Chemical compound C1=CC=CC=C1C1(C=2C=CC(=CC=2)[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 HITRWHKLCHWBNZ-UHFFFAOYSA-N 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 150000003672 ureas Chemical class 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
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 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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- 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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Abstract
提供一種電荷傳輸性塗料,其含有由式(1)表示之芳基胺衍生物所構成之電荷傳輸性物質、摻雜物及有機溶劑。
Description
本發明係關於電荷傳輸性塗料、電荷傳輸性薄膜及有機電致發光(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構成之電荷傳輸性薄膜。特別是電洞注入層,係負責陽極與電洞傳輸層或發光層之電荷授受,在達成有機EL元件之低電壓驅動及高輝度的目的上發揮重要的機能。
電洞注入層之形成方法,係粗分為以蒸鍍法為代表之乾式製程與以旋轉塗佈法為代表之濕式製程。比較此等各製程時,濕式製程較可有效率地製造大面積且平坦性高之薄膜。因此,於有機EL顯示器的大面積化正在進展的現在,期望能夠以濕式製程來形成之電洞注入層。
有鑑於如此之實情,本發明者等人,係有開發賦予可應用於各種濕式製程,而且應用於有機EL元件之電洞注入層時可實現優良之EL元件特性的薄膜之電荷傳輸性材料、或對使用於其之有機溶劑的溶解性良好之化
合物(例如參照專利文獻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
本發明之目的為提供與至今為止所開發之前述專利文獻的技術同樣地,會賦予可應用於各種濕式製程,且應用於有機EL元件之電洞注入層時可實現優良特性之薄膜的電荷傳輸性塗料。
本發明者等人為了達成前述目的重複努力探討的結果,發現由含有由特定之芳基胺衍生物所構成之電荷傳輸性物質、摻雜物及有機溶劑之塗料所得到之薄膜,具有高的電荷傳輸性,將該薄膜應用於有機EL元件之電洞注入層時,可實現優良特性及優良耐久性,而完成了本發明。
亦即,本發明提供下述電荷傳輸性塗料、電
荷傳輸性薄膜及有機EL元件。
1.一種電荷傳輸性塗料,其特徵為含有由式(1)表示之芳基胺衍生物所構成之電荷傳輸性物質、摻雜物及有機溶劑,
[式中,R1及R2係相互獨立地表示氫原子、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、碳數2~20之雜芳基、碳數1~20之烷氧基、碳數2~20之烯氧基、碳數2~20之炔氧基、碳數6~20之芳氧基、碳數2~20之雜芳氧基、或含有至少1個醚構造之碳數2~20之烷基,鍵結於此等之基的碳原子之氫原子的一部分或全部亦可被鹵素原子取代;R係相互獨立地表示鹵素原子、硝基、氰基、可經Z1取代之碳數1~20之烷基、可經Z1取代之碳數2~20之烯基、可經Z1取代之碳數2~20之炔基、可經Z1取代之碳數1~20之烷氧基、可經Z1取代之碳數2~20之烯氧基、或可經Z1取代之碳數2~20之炔氧基;Z1表示鹵素原子、硝基、氰基、可經Z2取代之碳數6~20之芳基、可經Z2取代之碳數2~20之雜芳基、可經
Z2取代之碳數1~20之烷氧基、可經Z2取代之碳數2~20之烯氧基、可經Z2取代之碳數2~20之炔氧基、可經Z2取代之碳數6~20之芳基、或可經Z2取代之碳數2~20之雜芳基;Z2表示鹵素原子、硝基或氰基;n係相互獨立地為0~5之整數、m係相互獨立地為0~4之整數、p係相互獨立地為0~3之整數]。
2.如1之電荷傳輸性塗料,其中R1及R2,均為碳數1~20之烷基或均為含有至少1個醚構造之碳數2~20之烷基。
3.如1或2之電荷傳輸性塗料,其中n、m及p均為0。
4.如1~3中任一項之電荷傳輸性塗料,其中前述摻雜物為雜多酸。
5.一種電荷傳輸性薄膜,其係使用如1~4中任一項之電荷傳輸性塗料所製作。
6.一種有機EL元件,其係具備如5之電荷傳輸性薄膜。
7.如6之有機EL元件,其中前述電荷傳輸性薄膜為電洞注入層。
8.一種以式(1')表示之芳基胺衍生物,
[式中,R1'及R2'係相互獨立地表示含有至少1個醚構造之碳數2~20之烷基,鍵結於該基之碳原子的氫原子之一部分或全部亦可被鹵素原子取代;R係相互獨立地表示鹵素原子、硝基、氰基、可經Z1取代之碳數1~20之烷基、可經Z1取代之碳數2~20之烯基、可經Z1取代之碳數2~20之炔基、可經Z1取代之碳數1~20之烷氧基、可經Z1取代之碳數2~20之烯氧基、或可經Z1取代之碳數2~20之炔氧基;Z1表示鹵素原子、硝基、氰基、可經Z2取代之碳數6~20之芳基、可經Z2取代之碳數2~20之雜芳基、可經Z2取代之碳數1~20之烷氧基、可經Z2取代之碳數2~20之烯氧基、可經Z2取代之碳數2~20之炔氧基、可經Z2取代之碳數6~20之芳基、或可經Z2取代之碳數2~20之雜芳基;Z2表示鹵素原子、硝基或氰基;n係相互獨立地為0~5之整數、m係相互獨立地為0~4之整數、p係相互獨立地為0~3之整數]。
本發明中所用之芳基胺衍生物容易溶解於有機溶劑,將之與摻雜物一起溶解於有機溶劑,可輕易地配製電荷傳輸性塗料。
由本發明之電荷傳輸性塗料所製作之薄膜,顯示高的電荷傳輸性,因此可適合使用作為以有機EL元件為首的電子裝置用薄膜。特別地,藉由將該薄膜應用於有機EL元件之電洞注入層,可得到特性優良之有機EL元件。
又,本發明之電荷傳輸性塗料,即使使用旋轉塗佈法或狹縫塗佈法等可大面積成膜之各種濕式製程,亦可再現性良好地製造電荷傳輸性優良之薄膜,因此亦可充分對應於近年來之有機EL元件領域的進展。
本發明之電荷傳輸性塗料,含有由下述式(1)表示之芳基胺衍生物所構成之電荷傳輸性物質。再者,本發明中,電荷傳輸性,係與導電性相同意義,且與電洞傳輸性相同意義。電荷傳輸性物質,可為其本身具有電荷傳輸性者、亦可為與電子接受性物質一起使用時具有電荷傳輸性者。電荷傳輸性塗料,可為其本身具有電荷傳輸性者、亦可為由其所得到之固體膜具有電荷傳輸性者。
式中,R1及R2係相互獨立地表示氫原子、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、碳數2~20之雜芳基、碳數1~20之烷氧基、碳數2~20之烯氧基、碳數2~20之炔氧基、碳數6~20之芳氧基、碳數2~20之雜芳氧基、或含有至少1個醚構造之碳數2~20之烷基。再者,鍵結於此等之基的碳原子之氫原子的一部分或全部,亦可經鹵素原子取代。
R係相互獨立地表示鹵素原子、硝基、氰基、可經Z1取代之碳數1~20之烷基、可經Z1取代之碳數2~20之烯基、可經Z1取代之碳數2~20之炔基、可經Z1取代之碳數1~20之烷氧基、可經Z1取代之碳數2~20之烯氧基、或可經Z1取代之碳數2~20之炔氧基。
Z1表示鹵素原子、硝基、氰基、可經Z2取代之碳數6~20之芳基、可經Z2取代之碳數2~20之雜芳基、可經Z2取代之碳數1~20之烷氧基、可經Z2取代之碳數2~20之烯氧基、可經Z2取代之碳數2~20之炔氧基、可經Z2取代之碳數6~20之芳基、或可經Z2取代之
碳數2~20之雜芳基。
Z2表示鹵素原子、硝基或氰基。
鹵素原子可列舉氟原子、氯原子、溴原子、碘原子等。
碳數1~20之烷基,係直鏈狀、分支狀、環狀之任意者均可,其具體例子,可列舉甲基、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之直鏈狀或分支狀烷基;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。
碳數2~20之烯基,係直鏈狀、分支狀、環狀之任意者均可,其具體例子,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。
碳數2~20之炔基,係直鏈狀、分支狀、環狀之任意者均可,其具體例子,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。
碳數6~20之芳基之具體例子,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。
碳數2~20之雜芳基之具體例子,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。
碳數1~20之烷氧基,係直鏈狀、分支狀、環狀之任意者均可,其具體例子,可列舉甲氧基、乙氧基、n-丙氧基、異丙氧基、n-丁氧基、異丁氧基、s-丁氧基、t-丁氧基、n-戊氧基、n-己氧基、n-庚氧基、n-辛氧基、n-壬氧基、n-癸氧基等之碳數1~20之直鏈狀或分支狀烷氧基;環丙氧基、環丁氧基、環戊氧基、環己氧基、環庚氧基、環辛氧基、環壬氧基、環癸氧基、雙環丁氧基、雙環戊氧基、雙環己氧基、雙環庚氧基、雙環辛氧基、雙環壬氧基、雙環癸氧基等之碳數3~20之環狀烷氧基。
碳數2~20之烯氧基,係直鏈狀、分支狀、環狀之任意者均可,其具體例子,可列舉乙烯氧基、n-1-丙烯氧基、n-2-丙烯氧基、1-甲基乙烯氧基、n-1-丁烯氧基、n-2-丁烯氧基、n-3-丁烯氧基、2-甲基-1-丙烯氧基、2-甲基-2-丙烯氧基、1-乙基乙烯氧基、1-甲基-1-丙烯氧
基、1-甲基-2-丙烯氧基、n-1-戊烯氧基、n-1-癸烯氧基、n-1-二十烯氧基等。
碳數2~20之炔氧基,係直鏈狀、分支狀、環狀之任意者均可,其具體例子,可列舉乙炔氧基、n-1-丙炔氧基、n-2-丙炔氧基、n-1-丁炔氧基、n-2-丁炔氧基、n-3-丁炔氧基、1-甲基-2-丙炔氧基、n-1-戊炔氧基、n-2-戊炔氧基、n-3-戊炔氧基、n-4-戊炔氧基、1-甲基-n-丁炔氧基、2-甲基-n-丁炔氧基、3-甲基-n-丁炔氧基、1,1-二甲基-n-丙炔氧基、n-1-己炔氧基、n-1-癸炔氧基、n-1-十五炔氧基、n-1-二十炔氧基等。
碳數6~20之芳氧基之具體例子,可列舉苯氧基、1-萘氧基、2-萘氧基、1-蒽氧基、2-蒽氧基、9-蒽氧基、1-菲氧基、2-菲氧基、3-菲氧基、4-菲氧基、9-菲氧基等。
碳數2~20之雜芳氧基之具體例子,可列舉2-噻吩氧基、3-噻吩氧基、2-呋喃氧基、3-呋喃氧基、2-噁唑氧基、4-噁唑氧基、5-噁唑氧基、3-異噁唑氧基、4-異噁唑氧基、5-異噁唑氧基、2-噻唑氧基、4-噻唑氧基、5-噻唑氧基、3-異噻唑氧基、4-異噻唑氧基、5-異噻唑氧基、2-咪唑氧基、4-咪唑氧基、2-吡啶氧基、3-吡啶氧基、4-吡啶氧基等。
含有至少1個醚構造之碳數2~20之烷基,可列舉至少1個亞甲基被氧原子取代之直鏈狀或分支狀之烷基。惟,並非鍵結於茀骨架之亞甲基被氧原子取代者、且
非鄰接之亞甲基同時被氧原子取代者。作為如此之基,考慮到原料化合物之獲得容易性時,較佳為以式(A)表示之基,其中更佳為以式(B)表示之基。
-(RAO)r-RB (A)
-(CH2CH2O)r-CH3 (B)(式中,RA表示碳數1~4之直鏈狀或分支狀之伸烷基,RB表示碳數1~[20-(RA之碳數)×r]之直鏈狀或分支狀之烷基,r為1~9之整數。由與摻雜物之相溶性的觀點,r較佳為2以上、更佳為3以上,由原料化合物之獲得容易性之觀點,較佳為5以下、更佳為4以下)。
含有至少1個醚構造之碳數2~20之烷基,可列舉-CH2OCH3、-CH2OCH2CH3、-CH2O(CH2)2CH3、-CH2OCH(CH3)2、-CH2O(CH2)3CH3、-CH2OCH2CH(CH3)2、-CH2OC(CH3)3、-CH2O(CH2)4CH3、-CH2OCH(CH3)(CH2)2CH3、-CH2O(CH2)2CH(CH3)2、-CH2OCH(CH3)(CH2)3CH3、-CH2O(CH2)5CH3、-CH2OCH2CH(CH3)(CH2)2CH3、-CH2O(CH2)2CH(CH3)CH2CH3、-CH2O(CH2)3CH(CH3)2、-CH2OC(CH3)2(CH2)2CH3、-CH2OCH(CH2CH3)(CH2)2CH3、-CH2OC(CH3)2CH(CH3)2、-CH2O(CH2)6CH3、-CH2O(CH2)7CH3、-CH2OCH2CH(CH2CH3)(CH2)3CH3、-CH2O(CH2)8CH3、-CH2O(CH2)9CH3、-CH2O(CH2)10CH3、-CH2O(CH2)11CH3、-CH2O(CH2)12CH3、-CH2O(CH2)13CH3、-CH2O(CH2)14CH3、-CH2O(CH2)15CH3、-CH2O(CH2)16CH3、-CH2O(CH2)17CH3、-CH2O(CH2)18CH3、-CH2CH2OCH3、-CH2CH2OCH2CH3、-CH2CH2O(CH2)2CH3、-CH2CH2OCH(CH3)2、
-CH2CH2O(CH2)3CH3、-CH2CH2OCH2CH(CH3)2、-CH2CH2OC(CH3)3、-CH2CH2O(CH2)4CH3、-CH2CH2OCH(CH3)(CH2)2CH3、-CH2CH2OCH2CH(CH3)2、-CH2CH2O(CH2)2CH(CH3)2、-CH2CH2OC(CH3)3、-CH2CH2OCH(CH3)(CH2)3CH3、-CH2CH2O(CH2)5CH3、-CH2CH2OCH(CH3)(CH2)3CH3、-CH2CH2OCH2CH(CH3)(CH2)2CH3、-CH2CH2O(CH2)2CH(CH3)CH2CH3、-CH2CH2O(CH2)3CH(CH3)2、-CH2CH2OC(CH3)2(CH2)2CH3、-CH2CH2OCH(CH2CH3)(CH2)2CH3、-CH2CH2OC(CH3)2CH(CH3)2、-CH2CH2O(CH2)6CH3、-CH2CH2O(CH2)7CH3、-CH2CH2OCH2CH(CH2CH3)(CH2)3CH3、-CH2CH2O(CH2)8CH3、-CH2CH2O(CH2)9CH3、-CH2CH2O(CH2)10CH3、-CH2CH2O(CH2)11CH3、-CH2CH2O(CH2)12CH3、-CH2CH2O(CH2)13CH3、-CH2CH2O(CH2)14CH3、-CH2CH2O(CH2)15CH3、-CH2CH2O(CH2)16CH3、-CH2CH2O(CH2)17CH3、-CH2CH2CH2OCH3、-CH2CH2CH2OCH2CH3、-CH2CH2CH2O(CH2)2CH3、-CH2CH2CH2OCH(CH3)2、-CH2CH2CH2O(CH2)3CH3、-CH2CH2CH2OCH2CH(CH3)2、-CH2CH2CH2OC(CH3)3、-CH2CH2CH2O(CH2)4CH3、-CH2CH2CH2OCH(CH3)(CH2)2CH3、-CH2CH2CH2OCH2CH(CH3)2、-CH2CH2CH2O(CH2)2CH(CH3)2、-CH2CH2CH2OC(CH3)3、-CH2CH2CH2OCH(CH3)(CH2)3CH3、-CH2CH2CH2O(CH2)5CH3、-CH2CH2CH2OCH(CH3)(CH2)3CH3、-CH2CH2CH2OCH2CH(CH3)(CH2)2CH3、-CH2CH2CH2O(CH2)2CH(CH3)CH2CH3、-CH2CH2CH2O(CH2)3CH(CH3)2、-CH2CH2CH2OC(CH3)2(CH2)2CH3、-CH2CH2CH2OCH(CH2CH3)(CH2)2CH3、-CH2CH2CH2OC(CH3)2CH(CH3)2、
-CH2CH2CH2O(CH2)6CH3、-CH2CH2CH2O(CH2)7CH3、-CH2CH2CH2OCH2CH(CH2CH3)(CH2)3CH3、-CH2CH2OCH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH3、-CH2CH2CH2OCH2CH2CH2OCH3、-CH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH3、-CH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH3、-CH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH3、-CH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH3、-CH2CH2CH2CH2OCH2CH2CH2CH2OCH2CH2CH2CH2OCH3、-CH2CH2CH2CH2OCH2CH2CH2CH2OCH2CH2CH2CH2OCH2CH2CH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH3、-CH2CH2OCH2CH2OCH2CH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH3、-CH2CH2CH2O(CH2)8CH3、-CH2CH2CH2O(CH2)9CH3、-CH2CH2CH2O(CH2)10CH3、-CH2CH2CH2O(CH2)11CH3、-CH2CH2CH2O(CH2)12CH3、-CH2CH2CH2O(CH2)13CH3、-CH2CH2CH2O(CH2)14CH3、-CH2CH2CH2O(CH2)15CH3、-CH2CH2CH2O(CH2)16CH3等。
R1及R2之至少一者,為前述烷基、烷氧基、烯氧基、炔氧基、芳氧基、雜芳氧基、或含有至少1個醚構造之烷基,較佳為兩者均為此等之基的任一者。特佳為兩者均為烷基、或兩者均為含有至少1個醚構造之烷基。
式(1)中,n係相互獨立地為0~5之整數、m係相互獨立地為0~4之整數、p係相互獨立地為0~3之整數。由提高本發明之茀衍生物的電荷傳輸性之觀點,n、m及p係相互獨立地為0~2較佳、0或1為更佳、0為最佳。特佳係n、m及p均為0。
前述芳基胺衍生物,可遵照下述合成流程A合成式(1')表示之中間體後,利用公知之偶合反應來合成。
鹵素原子可列舉氟原子、氯原子、溴原子、碘原子等。又,擬鹵素基可列舉甲烷磺醯氧基、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。
流程A之反應中所使用的溶劑,較佳為脂肪族烴類(戊烷、n-己烷、n-辛烷、n-癸烷、十氫萘等)、鹵化脂肪族烴類(二氯甲烷、1,2-二氯乙烷、四氯化碳等)、芳香族烴類(苯、甲苯、o-二甲苯、m-二甲苯、p-二甲苯、均三甲苯等)、醚類(二乙基醚、二異丙基醚、t-丁基甲基醚、四氫呋喃、1,4-二噁烷、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷等)、醯胺類(N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等)、尿素類(N,N-二甲基四氫咪唑酮、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)、水等;更佳為甲苯、四氫呋喃、二甲基亞碸、水等。
流程A之反應中所使用的觸媒,可列舉碘化鈉、碘化鉀、碘化銫、四丁基銨氟化物、四丁基銨氯化物、四丁基銨溴化物、四丁基銨碘化物、苄基三乙基銨氯化物、苄基三乙基銨溴化物、苄基三乙基銨碘化物、甲基三-n-辛基銨氯化物等。
反應溫度,通常係於自溶劑之熔點起至沸點之間適當決定,但通常為0~140℃。反應時間通常為0.1~100小時。
以下表示利用偶合反應,由式(1')表示之中間體合成前述芳基胺衍生物的方法之例子。
首先,如下述流程B所示,使式(1')表示之中間體與聯苯基硼酸化合物,於觸媒存在下反應,合成式(1")表示之中間體。
接著,如下述流程C所示,藉由使式(1")表示之中間體、與雙(聯苯基)胺化合物,於觸媒存在下進行交叉偶合反應,可合成式(1)表示之芳基胺衍生物。
流程B及C之反應中所使用的觸媒,可列舉[1,1'-雙(二苯基膦基)二茂鐵]鈀(II)二氯化物(PdCl2(dppf))、肆(三苯基膦)鈀(Pd(PPh3)4)、雙(三苯基膦)二氯鈀(Pd(PPh3)2Cl2)、雙(亞苄基丙酮)鈀(Pd(dba)2)、參(亞苄基丙酮)二鈀(Pd2(dba)3)、雙(三-t-丁基膦)鈀(Pd(P-t-Bu3)2)等之鈀觸媒等。
流程B及C之反應中所使用的溶劑,較佳為芳香族烴類(苯、甲苯、o-二甲苯、m-二甲苯、p-二甲苯、均三甲苯、異丙苯等)、醚類(二乙基醚、二異丙基醚、t-丁基甲基醚、四氫呋喃、1,4-二噁烷、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、二乙二醇二甲基醚等)、醇類(甲醇、乙醇、1-丙醇、2-丙醇等)、酮類(丙酮、甲基乙基酮、甲基異丁基酮、二-n-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)、腈類(乙腈、丙腈、丁腈等)、水等。
反應溫度,通常可為溶劑之熔點或-50℃至所使用的溶劑之沸點,較佳為0~140℃之範圍。反應時間通常為0.1~100小時。
反應結束後,可遵照一般方法進行後處理,得到目標之芳基胺衍生物。
本發明之電荷傳輸性塗料,係含有摻雜物。作為摻雜物並無特殊限定,其係無機系摻雜物、有機系摻雜物均可使用。
作為其中尤最佳之態樣,本發明之電荷傳輸性塗料,係含有雜多酸作為摻雜物。此時,可得到不僅來自以銦錫氧化物(ITO)、銦鋅氧化物(IZO)為代表之透明電極的高電洞接受能力,且亦顯示來自以鋁為代表之金屬陽極的高電洞接受能力之電荷傳輸性優良的薄膜。
雜多酸,代表而言係指具有以式(A1)表示之Keggin型或以式(A2)表示之Dawson型之化學構造所示之雜原子位於分子中心的構造,且係釩(V)、鉬(Mo)、鎢(W)等之含氧酸的同多酸、與異種元素之含氧酸進行縮合而成的多元酸。如此之異種元素之含氧酸,主要可列舉矽(Si)、磷(P)、砷(As)等之含氧酸。
雜多酸之具體例子,可列舉磷鉬酸、矽鉬酸、磷鎢酸、矽鎢酸、磷鎢鉬酸等。此等可1種單獨或組合2種以上使用。再者,本發明中所用之雜多酸,可作為市售品來獲得,又,亦可藉由公知之方法合成。
特別地,摻雜物為由1種之雜多酸所構成
時,該1種之雜多酸較佳為磷鎢酸或磷鉬酸、更佳為磷鎢酸。又,摻雜物為由2種以上之雜多酸所構成時,較佳為其中至少1種為磷鎢酸或磷鉬酸、更佳為磷鎢酸。
再者,雜多酸,不管是元素分析等之定量分析中,由一般式表示之構造來看,元素數為多或少,只要其係作為市售品所獲得者、或遵照公知之合成方法而適切地合成者,即可於本發明中使用。
亦即,例如,一般而言磷鎢酸係以化學式H3(PW12O40).nH2O表示、磷鉬酸係以化學式H3(PMo12O40).nH2O表示,但定量分析中,不管該式中之P(磷)、O(氧)或W(鎢)或Mo(鉬)之數目為多或少,只要其係作為市售品所獲得者、或遵照公知之合成方法而適切地合成者,即可於本發明中使用。此時,本發明所規定之雜多酸的質量,並非合成物或市售品中之純粹的磷鎢酸質量(磷鎢酸含量),而是意指能夠作為市售品而獲得的形態及能夠以公知之合成法單離的形態中,於包含水合水或其他雜質等的狀態下的全部質量。
本發明之電荷傳輸性塗料中所含的摻雜物,以質量比計,相對於電荷傳輸性物質1而言,為0.05~10.0左右。僅使用雜多酸作為摻雜物時,以質量比計,相對於電荷傳輸性物質1而言,雜多酸可為0.05~10.0左右,較佳為0.1~6.0左右。
本發明之電荷傳輸性塗料中所含的有機溶劑,只要係可良好地溶解前述芳基胺衍生物與摻雜物者,則無特殊限定,較佳為含有醯胺類、更佳為含有下述式(2)表示之酸醯胺衍生物。
式中,R11表示丙基或異丙基、較佳為異丙基。R12及R13係相互獨立地表示碳數1~4之烷基。碳數1~4之烷基,係直鏈狀、分支狀、環狀之任意者均可,具體而言可列舉甲基、乙基、n-丙基、異丙基、環丙基、n-丁基、異丁基、s-丁基、t-丁基、環丁基等。此等之中,R12及R13,較佳為甲基或乙基。
式(2)表示之酸醯胺衍生物,可列舉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(DMIB)、N,N-二乙基異丁醯胺、N-乙基-N-甲基異丁醯胺等。此等之中,特佳為DMIB。
式(2)表示之酸醯胺衍生物,可藉由對應之羧酸酯與胺的取代反應來合成、亦可使用市售品。
因為含有式(2)表示之酸醯胺衍生物,故使用本發明之電荷傳輸性塗料時,相較於以往的塗料,更加可藉由各種濕式製程而再現性良好地得到平坦性與均勻性優良之電荷傳輸性薄膜。
又,本發明所用之有機溶劑,亦可含有式(2)表示之酸醯胺衍生物以外的其他有機溶劑。如此之有機溶劑,可列舉N-甲基甲醯胺、N,N-二甲基甲醯胺、N,N-二乙基甲醯胺、N-甲基乙醯胺、N,N-二甲基乙醯胺、N-甲基丙醯胺、1,3-二甲基-2-四氫咪唑酮、N-甲基吡咯啶酮等之醯胺類;二乙二醇、三乙二醇、四乙二醇、二丙二醇、1,2-乙二醇(乙二醇)、1,2-丙二醇(丙二醇)、1,2-丁二醇、2,3-丁二醇、1,3-丁二醇、1,4-丁二醇、1,5-戊二醇、2-甲基-2,4-戊二醇(己二醇)、1,3-辛二醇、3,6-辛二醇等之二醇類;甘油等之三醇類;乙二醇單甲基醚、乙二醇單乙基醚、乙二醇單丙基醚、乙二醇單異丙基醚、乙二醇單丁基醚、乙二醇單異丁基醚、乙二醇單己基醚等之乙二醇單烷基醚類;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、丙二醇單己基醚等之丙二醇單烷基醚類等之烷二醇單烷基醚類;乙二醇單苯基醚等之乙二醇單芳基醚類;丙二醇單苯基醚等之丙二醇單芳基醚類等之烷二醇單芳基醚類;乙二醇單苄基醚等之乙二醇單芳烷基醚類;丙二醇單苄基醚等之丙二醇單芳烷基醚類等之烷二醇單芳烷基醚類;乙二醇丁氧基乙基醚等之乙二醇烷氧基烷基醚類;丙
二醇丁氧基乙基醚等之丙二醇烷氧基烷基醚類等之烷二醇烷氧基烷基醚類;乙二醇二甲基醚、乙二醇二乙基醚、乙二醇二丙基醚、乙二醇二異丙基醚、乙二醇二丁基醚等之乙二醇二烷基醚類;丙二醇二甲基醚、丙二醇二乙基醚、丙二醇二丙基醚、丙二醇二異丙基醚、丙二醇二丁基醚等之丙二醇二烷基醚類等之烷二醇二烷基醚類;乙二醇單甲基醚乙酸酯、乙二醇單乙基醚乙酸酯、乙二醇單丙基醚乙酸酯、乙二醇單異丙基醚乙酸酯、乙二醇單丁基醚乙酸酯等之乙二醇單烷基醚乙酸酯類;丙二醇單甲基醚乙酸酯、丙二醇單乙基醚乙酸酯、丙二醇單丙基醚乙酸酯、丙二醇單異丙基醚乙酸酯、丙二醇單丁基醚乙酸酯等之丙二醇單烷基醚乙酸酯類等之烷二醇單烷基醚乙酸酯類;乙二醇單乙酸酯等之乙二醇單乙酸酯類;丙二醇單乙酸酯等之丙二醇單乙酸酯類等之烷二醇單乙酸酯類;乙二醇二乙酸酯等之乙二醇二乙酸酯類;丙二醇二乙酸酯等之丙二醇二乙酸酯類等之烷二醇二乙酸酯類;二乙二醇單甲基醚、二乙二醇單乙基醚、二乙二醇單丙基醚、二乙二醇單異丙基醚、二乙二醇單丁基醚、二乙二醇單異丁基醚、二乙二醇單己基醚等之二乙二醇單烷基醚類;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、二丙二醇單己基醚等之二丙二醇單烷
基醚類等之二烷二醇單烷基醚類;二乙二醇單苯基醚等之二乙二醇單芳基醚類;二丙二醇單苯基醚等之二丙二醇單芳基醚類等之二烷二醇單芳基醚類;二乙二醇二甲基醚、二乙二醇二乙基醚、二乙二醇二丙基醚、二乙二醇二異丙基醚、二乙二醇二丁基醚等之二乙二醇二烷基醚類;二丙二醇二甲基醚、二丙二醇二乙基醚、二丙二醇二丙基醚、二丙二醇二異丙基醚、二丙二醇二丁基醚等之二丙二醇二烷基醚類等之二烷二醇二烷基醚類;二乙二醇單甲基醚乙酸酯、二乙二醇單乙基醚乙酸酯、二乙二醇單丙基醚乙酸酯、二乙二醇單異丙基醚乙酸酯、二乙二醇單丁基醚乙酸酯、二乙二醇單異丁基醚乙酸酯、二乙二醇單己基醚乙酸酯等之二乙二醇單烷基醚乙酸酯類;二丙二醇單甲基醚乙酸酯、二丙二醇單乙基醚乙酸酯、二丙二醇單丙基醚乙酸酯、二丙二醇單異丙基醚乙酸酯、二丙二醇單丁基醚乙酸酯、二丙二醇單異丁基醚乙酸酯、二丙二醇單己基醚乙酸酯等之二丙二醇單烷基醚乙酸酯類等之二烷二醇單烷基醚乙酸酯類;三乙二醇單甲基醚、三乙二醇單乙基醚等之三乙二醇單烷基醚類;三丙二醇單甲基醚、三丙二醇單乙基醚等之三丙二醇單烷基醚類等之三烷二醇單烷基醚類;三乙二醇二甲基醚、三乙二醇二乙基醚等之三乙二醇二烷基醚類;三丙二醇二甲基醚、三丙二醇二乙基醚等之
三丙二醇二烷基醚類等之三烷二醇二烷基醚類;1-丙醇、2-丙醇、1-丁醇、2-丁醇、1-戊醇、1-己醇、1-庚醇、1-壬醇、1-癸醇、1-十一醇、1-十二醇、1-十四醇等之直鏈脂肪族醇類;環己醇、2-甲基環己醇等之環狀脂肪族醇類等之脂肪族醇類;酚等之酚類;苄醇等之芳香族醇類;呋喃甲醇等之含有雜環之醇類;四氫呋喃甲醇等之含有氫化雜環之醇類;二異丙基醚、二-n-丁基醚、二-n-己基醚等之二烷基醚類;甲基苯基醚、乙基苯基醚、n-丁基苯基醚、苄基(3-甲基丁基)醚、(2-甲基苯基)甲基醚、(3-甲基苯基)甲基醚、(4-甲基苯基)甲基醚等之烷基芳基醚類;乙基苄基醚等之烷基芳烷基醚類;2-甲基呋喃、四氫呋喃、四氫吡喃等之環狀烷基單醚類;1,4-二噁烷等之環狀烷基二醚類;三噁烷等之環狀烷基三醚類;二縮水甘油醚等之二環氧基烷基醚類;乙基乙酸酯、n-丙基乙酸酯、異丙基乙酸酯、n-丁基乙酸酯、異丁基乙酸酯、s-丁基乙酸酯、t-丁基乙酸酯、n-戊基乙酸酯、(3-甲基丁基)乙酸酯、n-己基乙酸酯、(2-乙基丁基)乙酸酯、(2-乙基己基)乙酸酯等之直鏈
狀或分支狀烷基乙酸酯類;環己基乙酸酯、2-甲基環己基乙酸酯等之環狀烷基乙酸酯類等之烷基乙酸酯類;乙基丙酸酯、n-丙基丙酸酯、異丙基丙酸酯、n-丁基丙酸酯、異丁基丙酸酯、s-丁基丙酸酯、t-丁基丙酸酯、n-戊基丙酸酯、(3-甲基丁基)丙酸酯、n-己基丙酸酯、(2-乙基丁基)丙酸酯、(2-乙基己基)丙酸酯等之直鏈狀或分支狀烷基丙酸酯類;環己基丙酸酯、2-甲基環己基丙酸酯等之環狀烷基丙酸酯類等之烷基丙酸酯類;乙基丁酸酯、n-丙基丁酸酯、異丙基丁酸酯、n-丁基丁酸酯、異丁基丁酸酯、s-丁基丁酸酯、t-丁基丁酸酯、n-戊基丁酸酯、(3-甲基丁基)丁酸酯、n-己基丁酸酯、(2-乙基丁基)丁酸酯、(2-乙基己基)丁酸酯等之直鏈狀或分支狀烷基丁酸酯類;環己基丁酸酯、2-甲基環己基丁酸酯等之環狀烷基丁酸酯類等之烷基丁酸酯類;乙基乳酸酯、n-丙基乳酸酯、異丙基乳酸酯、n-丁基乳酸酯、異丁基乳酸酯、s-丁基乳酸酯、t-丁基乳酸酯、n-戊基乳酸酯、(3-甲基丁基)乳酸酯、n-己基乳酸酯、(2-乙基丁基)乳酸酯、(2-乙基己基)乳酸酯等之直鏈狀或分支狀烷基乳酸酯類;環己基乳酸酯、2-甲基環己基乳酸酯等之環狀烷基乳酸酯類等之烷基乳酸酯類等之烷基酯類;苄基乙酸酯等之芳烷基乙酸酯類;苄基丙酸酯等之芳烷基丙酸酯類;苄基丁酸酯等之芳烷基丁酸酯類;苄基乳酸酯等之芳烷基乳酸酯類等之芳烷基烷基酯類;二乙基酮、二異丁基酮、甲基乙基酮、甲基n-丙基
酮、甲基n-丁基酮、甲基異丁基酮、甲基n-丙基酮、甲基n-己基酮、乙基n-丁基酮、二-n-丙基酮等之二烷基酮類;異佛酮等之環狀烯基酮類;環己酮等之環狀烷基酮類;4-羥基-4-甲基-2-戊酮(二丙酮醇)等之羥基二烷基酮類;呋喃甲醛等之含有雜環之醛類;庚烷、辛烷、2,2,3-三甲基己烷、癸烷、十二烷等之直鏈狀或分支狀烷類;甲苯、二甲苯、o-二甲苯、m-二甲苯、p-二甲苯、均三甲苯、四氫萘、環己基苯等之烷基苯類;環己烷、甲基環己烷、乙基環己烷等之環狀烷類
等,但不限定於此等。此等溶劑可使用1種或2種以上。
又,本發明之電荷傳輸性塗料含有式(2)表示之酸醯胺以外的其他有機溶劑時,該其他有機溶劑較佳為包含二醇類、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等;更佳為包含二醇類、烷二醇單烷基醚類、二烷二醇單烷基醚類等;又更佳為包含二乙二醇、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、乙二醇單丙基醚、乙二醇單異丙基醚、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、二乙二醇單丙基醚、二乙二醇單異丙基醚、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等;又再更佳為包含二乙二醇、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、二丙二醇單甲基醚等。
使用式(2)表示之酸醯胺衍生物與其他有機溶劑作為有機溶劑時,全部有機溶劑中之該酸醯胺衍生物的含量,由再現性良好地實現膜的平坦性與均勻性之觀點,較佳為35質量%以上、更佳為50質量%以上、又更佳為55質量%以上、又再更佳為60質量%以上、又再更佳為70質量%以上,以後以75質量%以上、80質量%以上之順序為更佳。
本發明之電荷傳輸性塗料,係含有由前述芳基胺衍生物所構成之電荷傳輸性物質、摻雜物及有機溶劑者。
本發明之塗料的黏度,係依所製作之薄膜的厚度等或固體成分濃度來適當設定,但通常於25℃為
1~50mPa.s。
又,本發明中之電荷傳輸性塗料的固體成分濃度,係考量塗料之黏度及表面張力等、或所製作之薄膜的厚度等來適當設定,但通常為0.1~10.0質量%左右,考慮到提高塗料之塗佈性時,較佳為0.5~5.0質量%左右、更佳為1.0~3.0質量%左右。
電荷傳輸性塗料之配製方法並無特殊限定,可列舉例如使芳基胺衍生物先溶解於溶劑,對其添加摻雜物之方法;或使芳基胺衍生物與摻雜物的混合物溶解於溶劑之方法。有機溶劑有複數種時,可首先將芳基胺衍生物或摻雜物溶解於會充分溶解此等的溶劑中,再對其添加其他溶劑,亦可於複數種有機溶劑之混合溶劑中,依次或同時溶解芳基胺衍生物或摻雜物。
本發明中,由再現性良好地得到高平坦性薄膜之觀點,電荷傳輸性塗料較佳為使電荷傳輸性物質、摻雜物等溶解於有機溶劑後,使用次微米級之過濾器等過濾。
本發明之電荷傳輸性塗料,適合作為塗佈型電荷傳輸薄膜形成用塗料,藉由將該塗料塗佈於基材上並燒成,可於基材上形成電荷傳輸性薄膜。
塗料之塗佈方法,可列舉浸漬法、旋轉塗佈法、轉印印刷法、輥塗佈法、刷毛塗佈、噴墨法、噴霧
法、狹縫塗佈法等,但不限定於此等。考慮到再現性良好地得到平坦性高之電荷傳輸薄膜時,塗佈方法較佳為旋轉塗佈法、噴墨法、噴霧法等。再者,較佳為依塗佈方法來調節塗料之黏度及表面張力。
又,使用本發明之塗料時,為了得到具有均勻的成膜面及高的電荷傳輸性之薄膜,必須考慮與本發明所含的前述芳基胺衍生物一起含有的摻雜物或溶劑之種類等,來選擇燒成環境(大氣環境下、氮等之惰性氣體下、真空下等),但大部分的情況,藉由於大氣環境下燒成,即可得到均勻且電荷傳輸性優良之薄膜。
燒成溫度,係考量所得之薄膜的用途、對所得到之薄膜所賦予的電荷傳輸性之程度等,於100~260℃左右之範圍內適當設定,但使用所得到之薄膜作為有機EL元件之電洞注入層時,較佳為140~250℃左右、更佳為145~240℃左右。
再者,燒成時,亦能夠以表現更高之均勻成膜性、或於基材上使反應進行為目的,而附加2階段以上之溫度變化。加熱係例如使用加熱板或烘箱等適當的機器進行即可。
電荷傳輸性薄膜之膜厚並無特殊限定,作為有機EL元件之電洞注入層來使用時,較佳為5~200nm。使膜厚變化之方法,係有使塗料中之固體成分濃度變化、或使塗佈時之基板上的溶液量變化等之方法。
本發明之電荷傳輸性薄膜,於有機EL元件
中,可適合使用作為電洞注入層,但亦可使用作為電洞注入傳輸層等之電荷傳輸性機能層。
本發明之有機EL元件,係具有一對電極,且於此等電極之間,具有前述本發明之電荷傳輸性薄膜者。
作為有機EL元件之代表的構成,可列舉下述(a)~(f),但不限定於此等。再者,下述構成中,亦可依需要,於發光層與陽極之間設置電子阻擋層等,於發光層與陰極之間設置空穴(電洞)阻擋層等。又,電洞注入層、電洞傳輸層或電洞注入傳輸層亦可兼備作為電子阻擋層等之機能,電子注入層、電子傳輸層或電子注入傳輸層亦可兼備作為空穴(電洞)阻擋層等之機能。
(a)陽極/電洞注入層/電洞傳輸層/發光層/電子傳輸層/電子注入層/陰極
(b)陽極/電洞注入層/電洞傳輸層/發光層/電子注入傳輸層/陰極
(c)陽極/電洞注入傳輸層/發光層/電子傳輸層/電子注入層/陰極
(d)陽極/電洞注入傳輸層/發光層/電子注入傳輸層/陰極
(e)陽極/電洞注入層/電洞傳輸層/發光層/陰極
(f)陽極/電洞注入傳輸層/發光層/陰極
「電洞注入層」、「電洞傳輸層」及「電洞
注入傳輸層」,係指於發光層與陽極之間所形成的層,且係具有將電洞由陽極對發光層傳輸之機能者。於發光層與陽極之間,僅設置1層的電洞傳輸性材料之層時,其係「電洞注入傳輸層」,於發光層與陽極之間,設置2層以上的電洞傳輸性材料之層時,靠近陽極之層為「電洞注入層」、其以外之層為「電洞傳輸層」。特別地,電洞注入層及電洞注入傳輸層,係使用不僅來自陽極之電洞接受性,且分別對電洞傳輸層及發光層之電洞注入性亦優良的薄膜。
「電子注入層」、「電子傳輸層」及「電子注入傳輸層」,係指於發光層與陰極之間所形成的層,且係具有將電子由陰極對發光層傳輸之機能者。於發光層與陰極之間,僅設置有1層的電子傳輸性材料之層時,其係「電子注入傳輸層」,於發光層與陰極之間,設置有2層以上的電子傳輸性材料之層時,靠近陰極之層為「電子注入層」,其以外之層為「電子傳輸層」。
「發光層」係指具有發光機能之有機層,採用摻雜系統時,係包含主體材料與摻雜物材料。此時,主體材料,主要具有促進電子與電洞之再結合,將激子關閉在發光層內之機能,摻雜物材料,具有使因再結合而得到之激子有效率地發光之機能。磷光元件的情況時,主體材料主要具有將由摻雜物所生成之激子關閉在發光層內之機能。
使用本發明之電荷傳輸性塗料來製作有機EL
元件時的使用材料或製作方法,可列舉如下述者,但不限定於此等。
所使用之電極基板,較佳為以洗劑、醇、純水等預先進行液體洗淨而先淨化,例如,於陽極基板時,較佳為於臨使用前進行UV臭氧處理、氧-電漿處理等之表面處理。惟,陽極材料以有機物為主成分時,亦可不進行表面處理。
由本發明之電荷傳輸性塗料所得到之薄膜為電洞注入層時,本發明之有機EL元件之製作方法的一例,係如以下所述。
藉由前述方法,於陽極基板上塗佈本發明之電荷傳輸性塗料並燒成,於電極上製作電洞注入層。於此電洞注入層之上,依序設置電洞傳輸層、發光層、電子傳輸層、電子注入層、陰極。電洞傳輸層、發光層、電子傳輸層及電子注入層,係依所用之材料的特性等,以蒸鍍法或塗佈法(濕式製程)的任一者形成即可。
陽極材料可列舉以銦錫氧化物(ITO)、銦鋅氧化物(IZO)為代表之透明電極;或由以鋁為代表之金屬或此等之合金等所構成之金屬陽極,較佳為進行過平坦化處理者。亦可使用具有高電荷傳輸性之聚噻吩衍生物或聚苯胺衍生物。
再者,構成金屬陽極之其他金屬可列舉鈧、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,但不限定於此等。
形成電洞傳輸層之材料,可列舉(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(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(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"-聯三噻吩(BMA-3T)等之寡噻吩類等之電洞傳輸性低分子材料等。
形成發光層之材料,可列舉參(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)鋁(III)(BAlq)、4,4'-雙(2,2-二苯基乙烯基)聯苯、9,10-二(萘-2-基)蒽、2-t-丁基-9,10-二(萘-2-基)蒽、2,7-雙[9,9-二(4-甲基苯基)-茀-2-基]-9,9-二(4-甲基苯基)茀、2-甲基-9,10-雙(萘-2-基)蒽、2-(9,9-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)稠五苯、3,9-
二(萘-2-基)苝、3,10-二(萘-2-基)苝、參[4-(芘基)-苯基]胺、10,10'-二(聯苯-4-基)-9,9'-聯蒽、N,N'-二(萘-1-基)-N,N'-二苯基-[1,1':4',1":4",1'''-聯四苯]-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'-1m]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(p-甲苯基)茀、9,9-雙[4-(咔唑-9-基)-苯基]茀、2,7-雙(咔唑-9-基)-9,9-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)-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-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(二苯基磷醯基)-9-苯基-9H-茀-9-基)-9-苯基-9H-咔唑、4,4,8,8,12,12-六(p-甲苯基)-4H-8H-12H-12C-氮雜二苯并[cd,mn]芘、4,7-二(9H-咔唑-9-基)-1,10-啡啉、2,2'-雙(4-(咔唑-9-基)苯基)聯苯、2,8-雙(二苯基磷醯基)二苯并[b,d]噻吩、雙(2-甲基苯基)二苯基矽烷、雙[3,5-二(9H-咔唑-9-基)苯基]二苯基矽烷、3,6-雙(咔唑-9-基)-9-(2-乙基-己基)-9H-咔唑、3-(二苯基磷醯基)-9-(4-(二苯基磷醯基)苯基)-9H-咔唑、3,6-雙[(3,5-二苯基)苯基]-9-苯基咔唑等。亦可藉由將此等材料與發光性摻雜物予以共蒸鍍,來形成發光層。
發光性摻雜物,可列舉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)喹啉啶并(quinolidino)[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)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-乙基咔唑基)乙烯基]苯、4,4'-雙[4-(二-p-甲苯基胺基)苯乙烯基]聯苯、4-(二-p-甲苯基胺基)-4'-[(二-p-甲苯基胺基)苯乙烯基]二苯乙烯、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)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(m-甲苯基)胺基]-9,9-二甲基-茀-7-基}-9,9-二甲基-茀、N-(4-((E)-2-(6((E)-4-(二苯基胺基)苯乙烯基)萘-2-基)乙烯基)苯基)-N-苯基苯胺、fac-銥(III)參(1-苯基-3-甲基苯并咪唑啉-2-亞基-C,C2)、mer-銥(III)參(1-苯基-3-甲基苯并咪唑啉-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(2,4-二氟苯基吡啶)(5-(吡啶-2-基)-1H-四唑酸)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)吡唑酸)(苄基二苯基亞膦酸酯)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-吡啶基)-1,2,4-三唑)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑酸)(4',6'-二氟苯基吡啶酸)銥(III)、雙(4',6'-二氟苯基吡啶)(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)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑)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-久咯啶基-9-烯基-4H-吡喃、4-(二氰基亞甲基)-2-甲基-6-(1,1,7,7-四甲基久咯啶基-9-烯基)-4H-吡喃、4-(二氰基亞甲基)-2-t-丁基-6-(1,1,7,7-四甲基久咯啶-4-基-乙烯基)-4H-吡喃、參(二苄醯基甲烷)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)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-茀-2-基)-異喹啉](乙醯丙酮酸)銥(III)、雙[2-(9,9-二甲基-9H-茀-2-基)喹啉](乙醯丙酮酸)銥(III)、參[4,4'-二-t-丁基-(2,2')-聯吡啶]釕(III).雙(六氟磷酸酯)、參(2-苯基喹啉)銥(III)、雙(2-苯基喹啉)(乙醯丙酮酸)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)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)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)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)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)吡啶酸)銥(III)、雙(2-(9,9-二乙基-茀-2-基)-1-苯基-1H-苯并[d]咪唑(imidazolato))(乙醯丙酮酸)銥(III)、雙(2-苯基吡啶)(3-(吡啶-2-基)-2H-苯并吡喃-2-酮酸)銥(III)、雙(2-苯基喹啉)(2,2,6,6-四甲基庚烷-3,5-二酮酸)銥(III)、雙(苯基異喹啉)(2,2,6,6-四甲基庚烷-3,5-二酮酸)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)吡唑酸)(甲基二苯基膦)釕、雙[(4-n-己基苯基)異喹啉](乙醯丙酮酸)銥(III)、鉑(II)八乙基卟吩、雙(2-甲基二苯并[f,h]喹噁啉)(乙醯丙酮酸)銥(III)、參[(4-n-己基苯基)異喹啉]銥(III)等。
形成電子傳輸層之材料,可列舉8-羥基羥基喹啉-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-羥基喹啉)-4-(苯基酚)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-1-基)-3,5-二苯基-4H-1,2,4-三唑、2,9-雙(萘-2-基)-4,7-二苯基-1,10-啡啉、2,7-雙[2-(2,2'-聯吡啶-6-基)-1,3,4-噁二唑-5-基]-9,9-二甲基茀、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-2-基)苯基)-1H-咪唑并[4,5f][1,10]啡啉、2-(萘-2-基)-4,7-二苯基-1,10-啡啉、苯基-二芘基膦氧化物、3,3',5,5'-四[(m-吡啶基)-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)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,可列舉氧化鋰(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、鋰乙醯丙酮酸鹽(Li(acac))、乙酸鋰、安息香酸鋰等。
陰極材料可列舉鋁、鎂-銀合金、鋁-鋰合金、
鋰、鈉、鉀、銫等。
又,由本發明之電荷傳輸性塗料所得到之薄膜為電洞注入層時,本發明之有機EL元件之製作方法的其他之例子,係如以下所述。
前述之有機EL元件製作方法中,藉由依次形成電洞傳輸層、發光層,以取代進行電洞傳輸層、發光層、電子傳輸層、電子注入層之真空蒸鍍操作,可製作具有由本發明之電荷傳輸性塗料所形成之電荷傳輸性薄膜的有機EL元件。具體而言,於陽極基板上塗佈本發明之電荷傳輸性塗料,藉由前述方法製作電洞注入層,於其上依次形成電洞傳輸層、發光層,進而蒸鍍陰極材料,而成為有機EL元件。
所使用之陰極及陽極材料,可使用與前述為相同者,可進行同樣之洗淨處理、表面處理。
電洞傳輸層及發光層之形成方法,可列舉對電洞傳輸性高分子材料或發光性高分子材料、或於此等中添加有摻雜物之材料添加溶劑而進行溶解、或均勻分散,分別於電洞注入層或電洞傳輸層之上進行塗佈後,燒成藉以成膜之方法。
電洞傳輸性高分子材料,可列舉聚[(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'-聯伸苯基-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)]、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(end capped with polysilsesquioxane)、聚[(9,9-二二辛基茀基-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,可列舉聚(9,9-二烷基茀)(PDAF)等之聚茀衍生物、聚(2-甲氧基-5-(2'-乙基己氧基)-1,4-伸苯基伸乙烯基)(MEH-PPV)等之聚伸苯基伸乙烯基衍生物、聚(3-烷基噻吩)(PAT)等之聚噻吩衍生物、聚乙烯基咔唑(PVCz)等。
溶劑可列舉甲苯、二甲苯、氯仿等。溶解或均勻分散法,可列舉攪拌、加熱攪拌、超音波分散等之方法。
塗佈方法並無特殊限定,可列舉噴墨法、噴霧法、浸漬法、旋轉塗佈法、轉印印刷法、輥塗佈法、刷毛塗佈等。再者,塗佈較佳為在氮、氬等之惰性氣體下進行。
燒成方法可列舉在惰性氣體下或真空中,以烘箱或加熱板加熱之方法。
由本發明之電荷傳輸性塗料所得到之薄膜為電洞注入傳輸層時,本發明之有機EL元件之製作方法的一例,係如以下所述。
於陽極基板上形成電洞注入傳輸層,於該電洞注入傳輸層之上,依序設置發光層、電子傳輸層、電子
注入層、陰極。發光層、電子傳輸層及電子注入層之形成方法及具體例子,可列舉與前述者為相同者。
形成陽極材料、發光層、發光性摻雜物、電子傳輸層及電子阻擋層之材料、陰極材料,可列舉與前述者為相同者。
再者,亦可於電極及前述各層之間的任意之間,依需要設置空穴阻擋層、電子阻擋層等。例如,作為形成電子阻擋層之材料,可列舉參(苯基吡唑)銥等。
構成於陽極與陰極及此等之間所形成之層的材料,係於具備底部發光構造、頂部發光構造之何者的元件製造上相異,因此係考慮該點來選擇適當材料。
通常,於底部發光構造之元件中,於基板側係使用透明陽極,自基板側取出光,相對於此,於頂部發光構造之元件中,係使用由金屬所成之反射陽極,且由位於與基板相反方向的透明電極(陰極)側取出光。因此,例如提到陽極材料時,製造底部發光構造之元件時係使用ITO等之透明陽極、製造頂部發光構造之元件時係使用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,亦可遵照特定方法,依需要與捕水劑等一起進行密封。
以下,列舉實施例以更具體說明本發明,但本發明不受下述實施例限定。再者,所使用之裝置係如以
下所述。
(1)1H-NMR測定:日本電子(股)製、ECX-300
(2)ES-MS:Waters公司製、ZQ2000
(3)MALDI-TOF MS:Bruker Daltonics公司製、autoflex III smartbeam
(4)基板洗淨:長州產業(股)製、基板洗淨裝置(減壓電漿方式)
(5)塗料之塗佈:Mikasa(股)製、旋轉塗佈器MS-A100
(6)膜厚測定:(股)小坂研究所製、微細形狀測定機Surfcorder ET-4000
(7)有機EL元件之製作:長州產業(股)製、多機能蒸鍍裝置系統C-E2L1G1-N
(8)有機EL元件之輝度等之測定:(有)Tech World製、I-V-L測定系統
遵照日本特開2013-234169號公報記載之方法,合成下述式表示之化合物H1。
於燒瓶內加入2-溴-7-碘茀7.42g、二甲基亞碸30mL、碘化鉀330mg及氫氧化鉀2.81g後,於冰浴條件下一邊攪拌一邊滴下二乙二醇2-溴乙基甲基醚之二甲基亞碸混合液30mL(濃度:330g/L)。1.5小時後,移去冰浴,於室溫進一步攪拌58.5小時。對反應混合物添加離子交換水及乙酸乙酯,進行分液處理。將所得之有機層以離子交換水、飽和食鹽水進行分液洗淨,以硫酸鎂乾燥。將溶劑減壓餾去後,藉由二氧化矽凝膠管柱層析(展開溶劑:己烷/乙酸乙酯=40/60→0/100)進行分離、精製,收集含目標物之區分,將溶劑減壓餾去後,進行乾燥,得到下述式表示之中間體A(產量:8.16g、產率:62%)。1H-NMR及ES-MS之測定結果如以下所示。
1H-NMR(300MHz,CDCl3)δ[ppm]:7.74(d,J=1.4Hz,1H),7.67(dd,J=8.2,1.4Hz,1H),7.44-7.54(m,3H),7.39(d,J=8.2Hz,1H),3.47-3.55(m,8H),3.37-3.41(m,4H),3.34(s,6H),3.19-3.22(m,4H),2.79(t,J=7.2Hz,4H),2.33(t,
J=7.2Hz,4H)。
ES(+)-MS m/Z found:680.19([M+NH4]+ calcd:680.11)。
於燒瓶內加入中間體A4.97g、4-聯苯基硼酸1.49g、Pd(PPh3)4 175mg、甲苯35mL及碳酸鈉水溶液7mL(濃度:210g/L),回流攪拌4小時。放冷後,對反應混合物添加離子交換水及乙酸乙酯,進行分液處理。將所得之有機層以離子交換水、飽和食鹽水進行分液洗淨,以硫酸鎂乾燥。將溶劑減壓餾去後,藉由二氧化矽凝膠管柱層析(展開溶劑:己烷/乙酸乙酯=40/60→20/80)進行分離、精製,收集含目標物之區分,將溶劑減壓餾去後,進行乾燥,得到下述式表示之中間體B(產量:2.08g、產率:40%)。1H-NMR及ES-MS之測定結果如以下所示。
1H-NMR(300MHz,CDCL3)δ[ppm]:7.32-7.75(m,15H),3.42-3.51(m,8H),3.36-3.40(m,4H),3.30(s,6H),
3.20-3.23(m,4H),2.82-2.88(m,4H),2.39-2.45(m,4H)。
ES(+)-MS m/Z found:706.46([M+NH4]+ calcd:706.27)。
於燒瓶內加入中間體B2.08g、雙(4-聯苯基)胺1.06g、Pd(dba)2 51.8mg及t-丁氧基鈉397mg,進行氮取代後,添加甲苯15mL、預先配製之三-t-丁基膦之甲苯溶液0.5mL(濃度:73g/L),於80℃攪拌2小時。放冷後,對反應混合物添加離子交換水及乙酸乙酯,進行分液處理。將所得之有機層以離子交換水、飽和食鹽水進行分液洗淨,以硫酸鎂乾燥。將溶劑減壓餾去後,藉由二氧化矽凝膠管柱層析(展開溶劑:己烷/乙酸乙酯=70/30→0/100)進行分離、精製,收集含目標物之區分,將溶劑減壓餾去後,進行乾燥,得到下述式表示之化合物TEG-H1(產量:2.19g、產率:78%)。1H-NMR及
MALDI-TOF MS之測定結果如以下所示。
1H-NMR(300MHz,CDCl3)δ[ppm]:7.14-7.76(m,33H),3.41-3.52(m,12H),3.25-3.35(m,10H),2.86-2.99(m,4H),2.26-2.43(m,4H)。
MALDI-TOF MS m/Z found:929.07([m]+calcd:929.47)。
將化合物TEG-H1 0.052g及磷鎢酸(日本新金屬(股)製)0.010g,於氮環境下溶解於DMIB 2g並攪拌,將所得之溶液使用孔徑0.2μm之PTFE製過濾器過濾,得到電荷傳輸性塗料。
將化合物H1 0.025g及磷鎢酸(日本新金屬(股)
製)0.005g,於氮環境下溶解於DMIB 2g並攪拌,將所得之溶液使用孔徑0.2μm之PTFE製過濾器過濾,得到電荷傳輸性塗料。
將化合物TEG-H1 0.062g,於氮環境下溶解於DMIB 2g並攪拌,將所得之溶液使用孔徑0.2μm之PTFE製過濾器過濾,得到電荷傳輸性塗料。
將實施例1-1中得到之塗料,使用旋轉塗佈器塗佈於ITO基板後,於80℃乾燥1分鐘,進一步於大氣環境下、230℃燒成15分鐘,於ITO基板上形成25nm之均勻薄膜(電洞注入層)。作為ITO基板,係使用銦錫氧化物(ITO)於表面上以膜厚150nm被圖型化之25mm×25mm×0.7t的玻璃基板,使用前藉由O2電漿洗淨裝置(150W、30秒)去除表面上之雜質。
於其上使用蒸鍍裝置(真空度1.0×10-5Pa)層合α-NPD30nm。此時之蒸鍍速率,係設為0.2nm/秒。接著,將CBP與Ir(PPy)3共蒸鍍。共蒸鍍係以Ir(PPy)3之濃度成為6%的方式來控制蒸鍍速率,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,就BAlq及鋁而言為0.2nm/秒、就氟化鋰而言為
0.02nm/秒之條件分別進行,膜厚分別為20nm、0.5nm及100nm。
再者,為了防止空氣中之氧、水等之影響所致的特性劣化,有機EL元件係藉由密封基板密封後,評估其特性。密封係由以下順序進行。
於氧濃度2ppm以下、露點-85℃以下之氮環境中,使有機EL元件容納於密封基板之間,將密封基板以接著材料((股)MORESCO製MORESCO MOISTURE CUT WB90US(P))貼合。此時,將捕水劑(Dynic(股)製HD-071010W-40)與有機EL元件一起容納於密封基板內。對貼合之密封基板照射UV光(波長365nm、照射量6,000mJ/cm2)後,於80℃退火處理1小時,使接著材料硬化。
除了使用實施例1-2中得到之塗料以取代實施例1-1中得到之塗料以外,係以與實施例2-1相同之方法得到元件。
除了使用比較例1中得到之塗料以取代實施例1-1中得到之塗料以外,係以與實施例2-1相同之方法得到元件。
於驅動電壓10V時之電流密度、輝度、電流
效率、及輝度之半衰期(初期輝度5,000cd/m2)示於表1。
如表1所示,藉由使用由本發明之電荷傳輸性塗料所得到之電荷傳輸性薄膜作為電洞注入層,可得到具有優良之輝度特性、及耐久性的有機EL元件。
Claims (10)
- 一種電荷傳輸性塗料,其特徵為含有由式(1)表示之芳基胺衍生物所構成之電荷傳輸性物質、摻雜物及有機溶劑,[式中,R1及R2係均表示含有至少1個醚構造之碳數2~20之烷基,鍵結於此等之基的碳原子之氫原子的一部分或全部亦可被鹵素原子取代;R係相互獨立地表示鹵素原子、硝基、氰基、可經Z1取代之碳數1~20之烷基、可經Z1取代之碳數2~20之烯基、可經Z1取代之碳數2~20之炔基、可經Z1取代之碳數1~20之烷氧基、可經Z1取代之碳數2~20之烯氧基、或可經Z1取代之碳數2~20之炔氧基;Z1表示鹵素原子、硝基、氰基、可經Z2取代之碳數6~20之芳基、可經Z2取代之碳數2~20之雜芳基、可經Z2取代之碳數1~20之烷氧基、可經Z2取代之碳數2~20之烯氧基、可經Z2取代之碳數2~20之炔氧基、可經Z2取代之碳數6~20之芳基、或可經Z2取代之碳數2~20之雜芳基;Z2表示鹵素原子、硝基或氰基;n係相互獨立地為0~5之整數、m係相互獨立地為0~4之整數、p係相互獨立地為0~3之整數]。
- 如請求項1之電荷傳輸性塗料,其中n、m及p均為0。
- 如請求項1或2之電荷傳輸性塗料,其中前述摻雜物為雜多酸。
- 一種電荷傳輸性薄膜,其係使用如請求項1~3中任一項之電荷傳輸性塗料所製作。
- 一種有機電致發光元件,其係具備如請求項4之電荷傳輸性薄膜。
- 如請求項5之有機電致發光元件,其中前述電荷傳輸性薄膜為電洞注入層。
- 一種以式(1')表示之芳基胺衍生物,[式中,R1'及R2'均表示含有至少1個醚構造之碳數2~20之烷基,鍵結於該基之碳原子的氫原子之一部分或全部亦可被鹵素原子取代;R係相互獨立地表示鹵素原子、硝基、氰基、可經Z1取代之碳數1~20之烷基、可經Z1取代之碳數2~20之烯基、可經Z1取代之碳數2~20之炔基、可經Z1取代之碳數1~20之烷氧基、可經Z1取代之碳數2~20之烯氧基、或可經Z1取代之碳數2~20之炔氧基;Z1表示鹵素原子、硝基、氰基、可經Z2取代之碳數6~20之芳基、可經Z2取代之碳數2~20之雜芳基、可經Z2取代之碳數1~20之烷氧基、可經Z2取代之碳數2~20之烯氧基、可經Z2取代之碳數2~20之炔氧基、可經Z2取代之碳數6~20之芳基、或可經Z2取代之碳數2~20之雜芳基;Z2表示鹵素原子、硝基或氰基;n係相互獨立地為0~5之整數、m係相互獨立地為0~4之整數、p係相互獨立地為0~3之整數]。
- 如請求項1之電荷傳輸性塗料,其中前述含有至少1個醚構造之碳數2~20之烷基,係以下述式(A)表示者;-(RAO)r-RB (A)(式中,RA表示碳數1~4之直鏈狀或分支狀之伸烷基,RB表示碳數1~[20-(RA之碳數)×r]之直鏈狀或分支狀之烷基,r為1~9之整數)。
- 如請求項8之電荷傳輸性塗料,其中前述含有至少1個醚構造之碳數2~20之烷基,係以下述式(B)表示者;-(CH2CH2O)r-CH3 (B)(式中,r為1~9之整數)。
- 如請求項3之電荷傳輸性塗料,其中前述摻雜物為磷鎢酸。
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