CN106463636B - 电荷传输性清漆 - Google Patents
电荷传输性清漆 Download PDFInfo
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- CN106463636B CN106463636B CN201580029744.9A CN201580029744A CN106463636B CN 106463636 B CN106463636 B CN 106463636B CN 201580029744 A CN201580029744 A CN 201580029744A CN 106463636 B CN106463636 B CN 106463636B
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- 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
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- 238000001132 ultrasonic dispersion Methods 0.000 description 1
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- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
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- 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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Abstract
本发明提供电荷传输性清漆,其含有电荷传输性物质、非离子型含氟表面活性剂和有机溶剂,其中,非离子型含氟表面活性剂具有例如,由式(1)~(3)表示的含全氟烯基的全氟烃结构以及氧化烯结构;通过使用这样的电荷传输性清漆,可以获得当适用于空穴注入层时能够实现耐久性优良的有机EL元件的电荷传输性薄膜。
Description
技术领域
本发明涉及电荷传输性清漆,更详细地说,涉及含有非离子型含氟表面活性剂的电荷传输性清漆。
背景技术
有机电致发光(EL)元件被期待在显示器或照明等领域中的实用化,为了达到低电压驱动、高亮度、高寿命等的目的,人们在关于材料或元件结构方面进行了各种各样的开发。
在有机EL元件中使用多种功能性薄膜,作为其中之一的空穴注入层,承担着阳极与空穴传输层或发光层之间的电荷的授受,发挥着用于实现有机EL元件的低电压驱动和高亮度的重要功能。
该空穴注入层的形成方法大致分为以蒸镀法为代表的干式法以及以旋转涂布法为代表的湿式法。对这些方法进行比较,湿式法可以高效率地制造大面积且平坦性优良的薄膜,因此,特别是在显示器领域中,往往采用湿式法。
在这种状况下,本发明人等开发了各种含有苯胺衍生物作为电荷传输性物质的电荷传输性清漆(参见专利文献1~4),然而,关于空穴注入层用的湿式法材料经常被要求进行改善,特别是,由于能够有助于提高有机EL元件的亮度特性和寿命特性,对于能够形成平坦性优良的电荷传输性薄膜的材料的需求日益提高。
现有技术文献
专利文献
专利文献1:国际公开第2006/025342号
专利文献2:国际公开第2008/032616号
专利文献3:国际公开第2010/058777号
专利文献4:国际公开第2013/042623号
发明内容
发明所要解决的课题
本发明是鉴于上述情况而完成的,其目的是要提供能够形成平坦性良好的电荷传输性薄膜的电荷传输性清漆。
用于解决课题的手段
本发明人为了达到上述目的而反复进行了精心的研究,结果发现,通过使用在含有电荷传输性物质和有机溶剂的组合物中,配合具有含全氟烯基的全氟烃结构和氧化烯结构的非离子型含氟表面活性剂而调制成的电荷传输性清漆,可以提高所获薄膜的平坦性,例如在适用于带有堤(banks)的像素基板的情况下的像素内的膜的平坦性等,至此完成了本发明。
即,本发明提供:
1、电荷传输性清漆,其含有电荷传输性物质、非离子型含氟表面活性剂、和有机溶剂,其特征在于,
上述非离子型含氟表面活性剂具有含全氟烯基的全氟烃结构和氧化烯结构;
2、1所述的电荷传输性清漆,其中,上述全氟烯基为支链状全氟烯基;
3、1或2所述的电荷传输性清漆,其中,上述含全氟烯基的全氟烃结构由式(1)~(3)任一个表示;
[化1]
4、1~3的任1项所述的电荷传输性清漆,其中,上述氧化烯结构含有由-(A0O)n-(A0表示碳数2~10的亚烷基,n表示2~50的整数)表示的基团;
5、4所述的电荷传输性清漆,其中,上述氧化烯结构由-(CH2CH2O)n-(n如上所述)表示;
6、1~5的任1项所述的电荷传输性清漆,其中,还含有掺杂剂物质;
7、电荷传输性薄膜,其是使用1~6的任1项所述的电荷传输性清漆制作的;
8、电子器件,其具有7所述的电荷传输性薄膜;
9、有机电致发光元件,其具有7所述的电荷传输性薄膜;
10、9所述的有机电致发光元件,其中,上述电荷传输性薄膜构成空穴注入层;
11、电荷传输性薄膜的制造方法,其特征在于,将1~6的任1项所述的电荷传输性清漆涂布到基材上,并使溶剂蒸发。
发明的效果
本发明的电荷传输性清漆由于含有特定的非离子型含氟表面活性剂,因此,通过使用该清漆,可以适用于制作例如,能够形成在带有堤的像素基板的像素内平坦性也优良的薄膜等的高平坦性薄膜。
另外,尽管由本发明的电荷传输性清漆制得的薄膜含有非离子型含氟表面活性剂,但其表面的接触角与不含表面活性剂的薄膜相比也没有很大的差异。
进而,尽管本发明的电荷传输性薄膜含有作为绝缘材料的非离子型含氟表面活性剂,但对于具备该薄膜的有机EL元件特性也没有不良影响。
因此,本发明的电荷传输性清漆可以适用于以有机EL元件为代表的电子器件的薄膜制作,特别地,适用于有机EL元件的空穴注入层的制作。
另外,本发明的电荷传输性清漆即使在采用旋转涂布法或狭缝涂布法等可大面积成膜的各种湿法工艺的情况下,也能够再现性良好地制造电荷传输性优良的薄膜,因此,能够充分应对近年来在有机EL元件领域的进展。
具体实施方式
下面更详细地说明本发明。
本发明所述的电荷传输性清漆含有电荷传输性物质、非离子型含氟表面活性剂和有机溶剂,而非离子型含氟表面活性剂具有含全氟烯基的全氟烃结构和氧化烯结构。
作为本发明中使用的非离子型含氟表面活性剂所具有的含全氟烯基的全氟烃结构,没有特殊限定,可以是直链状、支链状中的任一种,在本发明中优选为含有支链的结构,更优选为含有支链状的全氟烯基的结构。
另外,作为其碳数,也没有特殊限定,优选为碳数2~20左右,更优选为碳数5~20,进一步优选为碳数5~15。
作为适宜的含全氟烯基的全氟烃结构,可列举出由式(1)表示的α-全氟壬烯基结构、或是由式(2)、(3)表示的结构,但不限定于这些结构。
[化2]
另一方面,作为氧化烯结构,也没有特殊限定,优选为含有由-(A0O)n-(A0表示碳数2~10的亚烷基,n表示2~50的整数)表示的基团的氧化烯结构,更优选为含有由-(CH2CH2O)n-(n如上所述)表示的氧化乙烯基的结构。
作为碳数2~10的亚烷基,可列举出亚乙基、亚丙基、三亚甲基、四亚甲基、五亚甲基、六亚甲基、七亚甲基、八亚甲基、九亚甲基、十亚甲基等。优选为碳数2~4的亚烷基。
另外,氧化烯链可以是一部分为支链,或者其亚烷基链中也可以具有羰基。
如果将含全氟烯基的全氟烃结构作为Rf,则作为能够适用于本发明的非离子型含氟表面活性剂,对于式(1)和(2)的结构,可列举出由式(A1)或(A2)表示的结构,对于式(3)的结构,可列举出由式(A3)表示的结构等,但不限定于这些结构。
Rf-O-(A0O)n-R0 (A1)
Rf-O-(A0O)n-Rf (A2)
R0-(OA0)n-O-Rf-O-(A0O)n-R0 (A3)
(式中,Rf相互独立地表示含全氟烯基的全氟烃结构;R0相互独立地表示氢原子或者碳数1~20的烷基。A0和n表示与上述相同的含义。)
作为碳数1~20的烷基,可以是直链状、支链状、环状中的任一种,可列举出例如,甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、正己基、正庚基、正辛基、正壬基、正癸基等碳数1~20的直链或支链状烷基;环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环壬基、环癸基、双环丁基、双环戊基、双环己基、双环庚基、双环辛基、双环壬基、双环癸基等碳数3~20的环状烷基等。
更优选地,Rf-O-为由式(1′)表示的α-全氟壬烯氧基结构,A0为亚乙基的结构,作为其具体例,可列举出α-全氟壬烯氧基-ω-甲基聚环氧乙烷、α-全氟壬烯氧基-ω-全氟壬烯基聚环氧乙烷等。
[化3]
予以说明,本发明中可使用的非离子型含氟表面活性剂,可以按照例如,特开2010-47680号公报、特开2011-57589号公报、特开2012-72287号公报等记载的方法来合成,另外,也可以作为市售品购入。
作为市售品的具体例,可列举出(株)Neos制的属于非离子型含氟表面活性剂的Ftergent M系列(251、212M、215M、250(α-全氟壬烯氧基-ω-甲基聚环氧乙烷))、同F系列(209F、222F、245F)、同G系列(208G、218GL、240G)、同P·D系列(212P、220P、228P、FTX-218、DFX-18)、低聚物系列(710FL、710FM、710FS、730FL、730LM)等,其中,优选M系列、F系列、G系列、P·D系列(212P、220P、228P)、低聚物系列(710FL、710FM、710FS)。
本发明中,非离子型含氟表面活性剂可以单独使用1种,也可以将2种以上组合使用。
对于非离子型含氟表面活性剂的使用量,只要能够发挥所需的平坦化效果、同时对所获薄膜的接触角和有机EL元件特性没有不良影响,就没有特殊限定,在电荷传输性清漆中,优选为0.001~10质量%左右,更优选为0.01~5质量%,进一步优选为0.01~2质量%。
作为本发明中使用的电荷传输性物质,只要是以往有机EL元件中使用的电荷传输性单体、电荷传输性低聚物或者聚合物,就没有限定,优选为电荷传输性低聚物。
作为电荷传输性低聚物的具体例,可列举出苯胺衍生物、噻吩衍生物、吡咯衍生物等各种空穴传输性物质,其中,优选为苯胺衍生物、噻吩衍生物,更优选为苯胺衍生物。
另外,电荷传输性低聚物的分子量通常为200~5,000,从调制能够形成电荷传输性优良的薄膜的清漆的观点考虑,优选为300以上,更优选为400以上,进一步优选为500以上;从调制能够形成平坦性优良的薄膜的均匀清漆的观点考虑,优选为4,000以下,更优选为3,000以下,进一步优选为2,000以下。
作为苯胺衍生物的具体例,可列举出由式(4)表示的苯胺衍生物,但不限定于这些衍生物。
[化4]
式(4)中,X1表示-NY1-、-O-、-S-、-(CR8R9)L-、或者单键,当m1或m2为0时,表示-NY1-。
Y1相互独立地表示氢原子、可被Z7取代的、碳数1~20的烷基、碳数2~20的烯基或者碳数2~20的炔基、或者可被Z8取代的、碳数6~20的芳基或者碳数2~20的杂芳基。
作为碳数1~20的烷基的具体例,可列举出与上述同样的烷基。
作为碳数2~20的烯基的具体例,可列举出乙烯基、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。
作为碳数2~20的炔基的具体例,可列举出乙炔基、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-丙炔基、正-1-戊炔基、正-2-戊炔基、正-3-戊炔基、正-4-戊炔基、1-甲基-正-丁炔基、2-甲基-正-丁炔基、3-甲基-正-丁炔基、1,1-二甲基-正-丙炔基、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。
作为碳数6~20的芳基的具体例,可列举出苯基、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。
作为碳数2~20的杂芳基的具体例,可列举出2-噻吩基、3-噻吩基、2-呋喃基、3-呋喃基、2-唑基、4-唑基、5-唑基、3-异唑基、4-异唑基、5-异唑基、2-噻唑基、4-噻唑基、5-噻唑基、3-异噻唑基、4-异噻唑基、5-异噻唑基、2-咪唑基、4-咪唑基、2-吡啶基、3-吡啶基、4-吡啶基等。
R8和R9相互独立地表示氢原子、卤原子、硝基、氰基、氨基、醛基、羟基、硫醇基、磺酸基、羧酸基、可被Z7取代的、碳数1~20的烷基、碳数2~20的烯基或者碳数2~20的炔基、可被Z8取代的、碳数6~20的芳基或者碳数2~20的杂芳基、或者-NHY2、-NY3Y4、-C(O)Y5、-OY6、-SY7、-SO3Y8、-C(O)OY9、-OC(O)Y10、-C(O)NHY11或者C(O)NY12Y13基。
Y2~Y13相互独立地表示可被Z7取代的、碳数1~20的烷基、碳数2~20的烯基或者碳数2~20的炔基、或者可被Z8取代的、碳数6~20的芳基或者碳数2~20的杂芳基。
Z7为卤原子、硝基、氰基、氨基、醛基、羟基、硫醇基、磺酸基、羧酸基、或者可被Z9取代的、碳数6~20的芳基或者碳数2~20的杂芳基。
Z8为卤原子、硝基、氰基、氨基、醛基、羟基、硫醇基、磺酸基、羧酸基、或者可被Z9取代的、碳数1~20的烷基、碳数2~20的烯基或者碳数2~20的炔基。
Z9为卤原子、硝基、氰基、氨基、醛基、羟基、硫醇基、磺酸基、或者羧酸基。
作为卤原子,可列举出氟原子、氯原子、溴原子、碘原子等。
此外,作为R7~R8和Y2~Y13的烷基、烯基、炔基、芳基以及杂芳基,可列举出与上述同样的基团。
其中,R8和R9优选为氢原子或者可被Z7取代的碳数1~20的烷基,更优选为氢原子或者可被Z7取代的甲基,以全部是氢原子为最佳。
L表示由-(CR8R9)-表示的2价亚烷基的重复单元数,为1~20的整数,优选为1~10,更优选为1~5,进一步优选为1~2,以1为最佳。
予以说明,当L为2以上时,多个R8可以彼此相同或不同,多个R9也可以彼此相同或不同。
特别地,X1优选为-NY1-或者单键。另外,Y1优选为氢原子或者可被Z7取代的碳数1~20的烷基,更优选为氢原子或者可被Z7取代的甲基,以氢原子为最佳。
R2~R5相互独立地表示氢原子、卤原子、硝基、氰基、氨基、醛基、羟基、硫醇基、磺酸基、羧酸基、可被Z7取代的、碳数1~20的烷基、碳数2~20的烯基或者碳数2~20的炔基、可被Z8取代的、碳数6~20的芳基或者碳数2~20的杂芳基、或者-NHY2、-NY3Y4、-C(O)Y5、-OY6、-SY7、-SO3Y8、-C(O)OY9、-OC(O)Y10、-C(O)NHY11或者C(O)NY12Y13(Y2~Y13表示与上述相同的含义)。作为这些卤原子、烷基、烯基、炔基、芳基和杂芳基,可列举出与上述同样的原子和基团。
特别地,在式(4)中,作为R2~R5,优选为氢原子、卤原子、可被Z7取代的碳数1~10的烷基、或者可被Z8取代的碳数6~14的芳基,更优选为氢原子、氟原子、或者可被氟原子取代的碳数1~10的烷基,以全部是氢原子为最佳。
另外,作为R6和R7,优选为氢原子、卤原子、可被Z7取代的碳数1~10的烷基、可被Z8取代的碳数6~14的芳基、或者可被Z8取代的二苯基氨基(Y3和Y4为可被Z8取代的苯基的-NY3Y4基),更优选为氢原子、氟原子、或者可被氟原子取代的二苯基氨基,进一步优选为同时为氢原子或者二苯基氨基。
而且,其中,优选R2~R5为氢原子、氟原子、可被氟原子取代的碳数1~10的烷基、R6和R7为氢原子、氟原子、可被氟原子取代的二苯基氨基、X1为-NY1-或者单键、且Y1为氢原子或者甲基的组合,更优选R2~R5为氢原子、R6和R7同时为氢原子或者二苯基氨基、X1为-NH-或者单键的组合。
式(4)中,m1和m2相互独立地表示0以上的整数,且满足1≤m1+m2≤20,从所获薄膜的电荷传输性与苯胺衍生物的溶解性的平衡考虑,优选满足2≤m1+m2≤8,更优选满足2≤m1+m2≤6,进一步优选满足2≤m1+m2≤4。
特别地,Y1~Y13和R2~R9中,取代基Z7优选为卤原子、或者可被Z9取代的碳数6~20的芳基,更优选为卤原子、或者可被Z9取代的苯基,以不存在(即,非取代)为最佳。
另外,取代基Z8优选为卤原子、或者可被Z9取代的碳数1~20的烷基,更优选为卤原子、或者可被Z9取代的碳数1~4的烷基,以不存在(即,非取代)为最佳。
另外,Z9优选为卤原子,更优选为氟原子,以不存在(即,非取代)为最佳。
Y1~Y13和R2~R9中,烷基、烯基和炔基的碳数优选为10以下,更优选为6以下,进一步优选为4以下。
另外,芳基和杂芳基的碳数优选为14以下,更优选为10以下,进一步优选为6以下。
上述苯胺衍生物的分子量通常为300~5,000,从提高溶解性的观点考虑,优选为4,000以下,更优选为3,000以下,进一步优选为2,000以下。
予以说明,作为上述苯胺衍生物的合成法,没有特殊限定,可列举出在Bulletinof 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)、国际公开第2008/032617号、国际公开第2008/032616号、国际公开第2008/129947号、国际公开第2013/084664号等中记载的方法。
作为由式(4)表示的苯胺衍生物的具体例,可列举出苯基二苯胺、苯基三苯胺、苯基四苯胺、苯基五苯胺、四苯胺(苯胺4聚物)、八苯胺(苯胺8聚物)、十六苯胺(苯胺16聚物)、以及由下述式表示的苯胺衍生物,但不限定于这些例子。
[化5]
(式中,DPA表示二苯基氨基。)
[化6]
(式中,Ph表示苯基,TPA表示对-(二苯基氨基)苯基。)
为了提高电荷传输能等,本发明的电荷传输性清漆也可以根据需要,含有掺杂剂物质。
作为掺杂剂物质,只要是能够溶解于在清漆中使用的至少一种溶剂中的,就没有特殊限定,可以使用无机系掺杂剂物质、有机系掺杂剂物质中的任一种。
作为无机系的掺杂剂物质,可列举出氯化氢、硫酸、硝酸、磷酸等无机酸;氯化铝(III)(AlCl3)、四氯化钛(IV)(TiCl4)、三溴化硼(BBr3)、三氟化硼醚配合物(BF3·OEt2)、氯化铁(III)(FeCl3)、氯化铜(II)(CuCl2)、五氯化锑(V)(SbCl5)、五氟化锑(V)(SbF5)、五氟化砷(V)(AsF5)、五氟化磷(PF5)、三(4-溴苯基)六氯锑酸铝(TBPAH)等金属卤化物;Cl2、Br2、I2、ICl、ICl3、IBr、IF4等卤素;磷钼酸、磷钨酸等杂多酸等。
作为有机系掺杂剂物质,可列举出苯磺酸、甲苯磺酸、对-苯乙烯磺酸、2-萘磺酸、4-羟基苯磺酸、5-磺基水杨酸、对-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、国际公开第2005/000832号记载的1,4-苯并二烷二磺酸化合物、国际公开第2006/025342号记载的芳基磺酸化合物、国际公开第2009/096352号记载的芳基磺酸化合物、聚苯乙烯磺酸等芳基磺酸化合物;10-樟脑磺酸等非芳基磺酸化合物;7,7,8,8-四氰基苯醌二甲烷(TCNQ)、2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ)等有机氧化剂。
这些无机系和有机系的掺杂剂物质可以单独使用1种,也可以将2种以上组合使用。
在这些掺杂剂物质中,优选为杂多酸,通过使用杂多酸作为掺杂剂物质,可以获得不仅显示来自以氧化铟锡(ITO)、氧化铟锌(IZO)为代表的透明电极的高空穴受容能力,而且显示来自以铝为代表的金属阳极的高空穴受容能力的电荷传输性优良的薄膜。
所谓杂多酸,是指具有以代表性的式(B1)所示Keggin型或者式(B2)所示Dawson型的化学结构来表示的、杂原子位于分子中心的结构,由钒(V)、钼(Mo)、钨(W)等的含氧酸的同多酸与不同元素的含氧酸缩合而成的多酸。作为这种不同元素的含氧酸,主要可列举出硅(Si)、磷(P)、砷(As)的含氧酸。
[化7]
作为杂多酸的具体例,可列举出:磷钼酸、硅钼酸、磷钨酸、硅钨酸、磷钨钼酸等,它们可以单独使用,也可以将2种以上组合使用。予以说明,本发明中使用的杂多酸可以作为市售品购得,另外,也可以采用公知的方法来合成。
特别地,当掺杂剂物质包含单独1种杂多酸时,该1种杂多酸优选为磷钨酸或者磷钼酸,以磷钨酸为最佳。另外,当掺杂剂物质包含2种以上杂多酸时,该2种以上杂多酸中的1个优选为磷钨酸或者磷钼酸,更优选为磷钨酸。
予以说明,作为杂多酸,在元素分析等定量分析中,按照通式所示结构,不管杂多酸中的元素个数是多的或者是少的,只要它是作为市售品购得的、或者按照公知的合成方法适当合成的,均可以在本发明中使用。
即,例如,一般而言,磷钨酸由化学式H3(PW12O40)·nH2O表示,磷钼酸由化学式H3(PMo12O40)·nH2O表示,但在定量分析中,该式中的P(磷)、O(氧)或W(钨)或Mo(钼)的个数可能多些或者少些,只要它们是作为市售品购得的、或者按照公知的合成方法适当合成的,就可以在本发明中使用。该情况下,本发明中规定的杂多酸的质量不是指合成物或市售品中的纯的磷钨酸的质量(磷钨酸含量),而是指在可作为市售品购得的形态以及按照公知的合成法可分离的形态中,含有水合水或其他杂质等的状态的全部质量。
另外,作为掺杂剂物质,也优选使用芳基磺酸化合物。特别优选由式(5)或者(6)表示的芳基磺酸化合物。
[化8]
A1表示O或者S,优选为O。
A2表示萘环或者蒽环,优选为萘环。
A3表示2~4价的全氟联苯基,p表示A1与A3键合的个数,为满足2≤p≤4的整数,优选是A3为2价全氟联苯基,且p为2。
q表示与A2键合的磺酸基个数,为满足1≤q≤4的整数,以2为最佳。
A4~A8相互独立地表示氢原子、卤原子、氰基、碳数1~20的烷基、碳数1~20的卤代烷基、或者碳数2~20的卤代烯基,A4~A8中的至少3个为卤原子。
作为碳数1~20的卤代烷基,可列举出三氟甲基、2,2,2-三氟乙基、1,1,2,2,2-五氟乙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、1,1,2,2,3,3,3-七氟丙基、4,4,4-三氟丁基、3,3,4,4,4-五氟丁基、2,2,3,3,4,4,4-七氟丁基、1,1,2,2,3,3,4,4,4-九氟丁基等。
作为碳数2~20的卤代烯基,可列举出全氟乙烯基、全氟丙烯基(烯丙基)、全氟丁烯基等。
此外,作为卤原子、碳数1~20的烷基的例子,可列举出与上述同样的原子和基团,作为卤原子,优选为氟原子。
其中,优选是A4~A8为氢原子、卤原子、氰基、碳数1~10的烷基、碳数1~10的卤代烷基、或者碳数2~10的卤代烯基,且A4~A8中的至少3个为氟原子,更优选为氢原子、氟原子、氰基、碳数1~5的烷基、碳数1~5的氟代烷基、或者碳数2~5的氟代烯基、且A4~A8中的至少3个为氟原子,进一步优选为氢原子、氟原子、氰基、碳数1~5的全氟烷基、或者碳数1~5的全氟烯基、且A4、A5和A8为氟原子。
予以说明,全氟烷基是指烷基的全部氢原子被氟原子取代而成的基团;全氟烯基是指烯基的全部氢原子被氟原子取代而成的基团。
r表示与萘环键合的磺酸基个数,为满足1≤r≤4的整数,优选为2~4,以2为最佳。
对于作为掺杂剂物质使用的芳基磺酸化合物的分子量,没有特殊限定,当与电荷传输性低聚物一起使用时,从在有机溶剂中的溶解性等考虑,优选为2000以下,更优选为1500以下。
以下列举出本发明中适宜作为掺杂剂物质的芳基磺酸化合物的具体例,但不限定于这些物质。
[化9]
在本发明的电荷传输性清漆中含有掺杂剂物质的情况下,掺杂剂物质的使用量可以根据掺杂剂物质的种类、所需电荷传输性的程度等来适宜确定,不能一概而论,一般而言,按照质量比计,相对于电荷传输性物质1,为0.01~50的范围内。
作为调制电荷传输性清漆时使用的有机溶剂,可以使用那些能够将电荷传输性物质、非离子型含氟表面活性剂以及根据需要使用的掺杂剂物质良好地溶解的高溶解性溶剂。
作为这类高溶解性溶剂,可列举出例如,环己酮、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基吡咯烷酮、1,3-二甲基-2-咪唑烷酮、二甘醇单甲醚等有机溶剂,但不限定于这些溶剂。这些溶剂可以单独使用1种,或者将2种以上混合使用,相对于清漆中所使用的溶剂全体,其使用量可以为5~100质量%。
予以说明,电荷传输性物质、非离子型含氟表面活性剂等优选均能成为完全溶解于或者均匀分散于任何上述溶剂中的状态,更优选为完全溶解的状态。
另外,本发明中,通过使清漆含有至少1种在25℃的粘度为10~200mPa·s、特别是35~150mPa·s、在常压(大气压)下的沸点为50~300℃、特别是150~250℃的高粘度有机溶剂,可以使清漆的粘度的调整变得容易,其结果,可以调制一类能够再现性良好地形成平坦性优良的薄膜的、适于所采用的涂布方法的清漆。
作为高粘度有机溶剂,可列举出例如,环己醇、乙二醇、乙二醇二缩水甘油醚、1,3-辛二醇、二甘醇、二丙二醇、三甘醇、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,但不限定于这些溶剂。这些溶剂可以单独使用,也可以将2种以上混合使用。
相对于本发明清漆中所用的溶剂全体,高粘度有机溶剂的添加比例优选在不析出固体的范围内,只要不析出固体,添加比例优选为5~90质量%。
进而,为了提高对基板的润湿性、调整溶剂的表面张力、调整极性、调整沸点等,也可以按照相对于清漆中所用的溶剂全体为1~90质量%、优选为1~50质量%的比例混合入其他溶剂。
作为这类溶剂,可列举出例如,丙二醇单甲醚、乙二醇单丁醚、二甘醇二乙醚、二甘醇二甲醚、二甘醇单乙基醚乙酸酯、二甘醇单丁基醚乙酸酯、二丙二醇单甲醚、丙二醇单甲基醚乙酸酯、二甘醇单乙醚、二丙酮醇、γ-丁内酯、乳酸乙酯、乙酸正己酯等,但不限定于这些溶剂。这些溶剂可以单独使用1种,或者将2种以上混合使用。
本发明的清漆的粘度可根据所需制作的薄膜的厚度等或固体成分的浓度来适宜设定,通常在25℃为1~50mPa·s。
另外,本发明的电荷传输性清漆的固体成分浓度,可根据清漆的粘度和表面张力等,以及所需制作的薄膜的厚度等来适宜设定,通常为0.1~10.0质量%左右,从提高清漆的涂布性考虑,优选为0.5~5.0质量%左右,更优选为1.0~3.0质量%左右。
将上述的电荷传输性清漆涂布在基材上,通过烘烤使其在基材上形成电荷传输性薄膜。
作为清漆的涂布方法,没有特殊限定,可举出浸涂法、旋转涂布法、转印法、辊涂法、刷涂法、喷墨法、喷涂法、狭缝涂布法等,优选根据涂布方法来调节清漆的粘度和表面张力。
另外,当使用本发明的清漆时,对于烘烤气氛没有特殊限定,不仅在大气气氛中,而且在氮气等惰性气体或真空中,都能得到具有均匀成膜面和高电荷传输性的薄膜。
从所获薄膜的用途、向所获薄膜赋予的电荷传输性的程度、溶剂的种类和沸点等考虑,烘烤温度可在100~260℃左右的范围内适宜设定,当将所获薄膜用作有机EL元件的空穴注入层时,优选为140~250℃左右,更优选为145~240℃左右。
予以说明,烘烤时,为了使其显现更优良的均匀成膜性,或是为了使其在基材上进行反应,可以采用2阶段以上的温度变化,使用例如加热板或烘箱等适当的设备进行加热。
对电荷传输性薄膜的膜厚没有特殊限定,当在有机EL元件内用作空穴注入层时,优选为5~200nm。作为使膜厚发生变化的方法,有改变清漆中的固体成分浓度、或是改变涂布时基板上的溶液量等的方法。
当使用本发明的电荷传输性清漆制作OLED元件时,作为其使用材料和制作方法,可列举出下述的材料和方法,但不限定于此。
所使用的电极基板优选预先通过用洗涤剂、醇、纯水等进行液体洗涤来净化,例如,优选在临使用前对阳极基板进行UV臭氧处理、氧-等离子体处理等表面处理。但是,当阳极材料以有机物作为主要成分时,也可以不进行表面处理。
具有包含由本发明电荷传输性清漆制得的薄膜的空穴注入层的OLED元件,其制作方法的例子如下。
采用上述的方法,在阳极基板上涂布本发明的电荷传输性清漆,并进行烘烤,在电极上制作空穴注入层。将其导入到真空蒸镀装置内,依次蒸镀空穴传输层、发光层、电子传输层、电子传输层/空穴阻断层、阴极金属,制成OLED元件。予以说明,也可以根据需要,在发光层与空穴传输层之间设置电子阻断层。
作为阳极材料,可列举出以氧化铟锡(ITO)、氧化铟锌(IZO)为代表的透明电极、由以铝为代表的金属或它们的合金等构成的金属阳极,优选事先进行平坦化处理。也可以使用具有高电荷传输性的聚噻吩衍生物或聚苯胺衍生物。
予以说明,作为构成金属阳极的其他金属,可列举出钪、钛、钒、铬、锰、铁、钴、镍、铜、锌、镓、钇、锆、铌、钼、钌、铑、钯、镉、铟、钪、镧、铈、镨、钕、钷、钐、铕、钆、铽、镝、钬、铒、铥、镱、铪、铊、钨、铼、锇、铱、铂、金、钛、铅、铋或它们的合金等,但不限定于这些金属。
作为形成空穴传输层的材料,可列举出(三苯胺)二聚物衍生物、[(三苯胺)二聚物]螺二聚物、N,N'-双(萘-1-基)-N,N'-双(苯基)-联苯胺(α-NPD)、N,N'-双(萘-2-基)-N,N'-双(苯基)-联苯胺、N,N'-双(3-甲基苯基)-N,N'-双(苯基)-联苯胺、N,N'-双(3-甲基苯基)-N,N'-双(苯基)-9,9-螺联芴、N,N'-双(萘-1-基)-N,N'-双(苯基)-9,9-螺联芴、N,N'-双(3-甲基苯基)-N,N'-双(苯基)-9,9-二甲基-芴、N,N'-双(萘-1-基)-N,N'-双(苯基)-9,9-二甲基-芴、N,N'-双(3-甲基苯基)-N,N'-双(苯基)-9,9-二苯基-芴、N,N'-双(萘-1-基)-N,N'-双(苯基)-9,9-二苯基-芴、N,N'-双(萘-1-基)-N,N'-双(苯基)-2,2'-二甲基联苯胺、2,2',7,7'-四(N,N-二苯基氨基)-9,9-螺联芴、9,9-双[4-(N,N-双-联苯-4-基-氨基)苯基]-9H-芴、9,9-双[4-(N,N-双-萘-2-基-氨基)苯基]-9H-芴、9,9-双[4-(N-萘-1-基-N-苯基氨基)-苯基]-9H-芴、2,2',7,7'-四[N-萘基(苯基)-氨基]-9,9-螺联芴、N,N'-双(菲-9-基)-N,N'-双(苯基)-联苯胺、2,2'-双[N,N-双(联苯-4-基)氨基]-9,9-螺联芴、2,2'-双(N,N-二苯基氨基)-9,9-螺联芴、二-[4-(N,N-二(对-甲苯基)氨基)-苯基]环己烷、2,2',7,7'-四(N,N-二(对-甲苯基))氨基-9,9-螺联芴、N,N,N',N'-四-萘-2-基-联苯胺、N,N,N',N'-四-(3-甲基苯基)-3,3'-二甲基联苯胺、N,N'-二(萘基)-N,N'-二(萘-2-基)-联苯胺、N,N,N',N'-四(萘基)-联苯胺、N,N'-二(萘-2-基)-N,N'-二苯基联苯胺-1,4-二胺、N1,N4-二苯基-N1,N4-二(间甲苯基)苯-1,4-二胺、N2,N2,N6,N6-四苯基萘-2,6-二胺、三(4-(喹啉-8-基)苯基)胺、2,2'-双(3-(N,N-二(对-甲苯基)氨基)苯基)联苯、4,4',4”-三[3-甲基苯基(苯基)氨基]三苯胺(m-MTDATA)、4,4',4”-三[1-萘基(苯基)氨基]三苯胺(1-TNATA)等三芳基胺类、5,5”-双-{4-[双(4-甲基苯基)氨基]苯基}-2,2':5',2”-三联噻吩(BMA-3T)等低聚噻吩类等。
作为形成发光层的材料,可列举出三(8-羟基喹啉)铝(III)(Alq3)、双(8-羟基喹啉)锌(II)(Znq2)、双(2-甲基-8-羟基喹啉)(对-苯基苯酚)铝(III)(BAlq)、4,4'-双(2,2-二苯基乙烯基)联苯、9,10-二(萘-2-基)蒽、2-叔丁基-9,10-二(萘-2-基)蒽、2,7-双[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-双(萘-2-基)蒽、2-(9,9-螺联芴-2-基)-9,9-螺联芴、2,7-双(9,9-螺联芴-2-基)-9,9-螺联芴、2-[9,9-二(4-甲基苯基)-芴-2-基]-9,9-二(4-甲基苯基)芴、2,2'-二芘基-9,9-螺联芴、1,3,5-三(芘-1-基)苯、9,9-双[4-(芘基)苯基]-9H-芴、2,2'-双(9,10-二苯基蒽)、2,7-二芘基-9,9-螺联芴、1,4-二(芘-1-基)苯、1,3-二(芘-1-基)苯、6,13-二(联苯-4-基)并五苯、3,9-二(萘-2-基)苝、3,10-二(萘-2-基)苝、三[4-(芘基)-苯基]胺、10,10'-二(联苯-4-基)-9,9'-联蒽、N,N'-二(萘-1-基)-N,N'-二苯基-[1,1':4',1”:4”,1”'-四联苯基]-4,4”'-二胺、4,4'-二[10-(萘-1-基)蒽-9-基]联苯、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'-联蒽-10-基)-9,9-二甲基-9H-芴-2-基)芘、1-(7-(9,9'-联蒽-10-基)-9,9-二己基-9H-芴-2-基)芘、1,3-双(咔唑-9-基)苯、1,3,5-三(咔唑-9-基)苯、4,4',4”-三(咔唑-9-基)三苯胺、4,4'-双(咔唑-9-基)联苯(CBP)、4,4'-双(咔唑-9-基)-2,2'-二甲基联苯、2,7-双(咔唑-9-基)-9,9-二甲基芴、2,2',7,7'-四(咔唑-9-基)-9,9-螺联芴、2,7-双(咔唑-9-基)-9,9-二(对-甲苯基)芴、9,9-双[4-(咔唑-9-基)-苯基]芴、2,7-双(咔唑-9-基)-9,9-螺联芴、1,4-双(三苯基甲硅烷基)苯、1,3-双(三苯基甲硅烷基)苯、双(4-N,N-二乙氨基-2-甲基苯基)-4-甲基苯基甲烷、2,7-双(咔唑-9-基)-9,9-二辛基芴、4,4”-二(三苯基甲硅烷基)-对-三联苯、4,4'-二(三苯基甲硅烷基)联苯、9-(4-叔丁基苯基)-3,6-双(三苯基甲硅烷基)-9H-咔唑、9-(4-叔丁基苯基)-3,6-二三苯甲基-9H-咔唑、9-(4-叔丁基苯基)-3,6-双(9-(4-甲氧基苯基)-9H-芴-9-基)-9H-咔唑、2,6-双(3-(9H-咔唑-9-基)苯基)吡啶、三苯基(4-(9-苯基-9H-芴-9-基)苯基)硅烷、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-双(3-(9H-咔唑-9-基)苯基)吡啶、9,9-螺联芴-2-基-二苯基-氧化膦、9,9'-(5-(三苯基甲硅烷基)-1,3-亚苯基)双(9H-咔唑)、3-(2,7-双(二苯基磷酰基)-9-苯基-9H-芴-9-基)-9-苯基-9H-咔唑、4,4,8,8,12,12-六(对-甲苯基)-4H-8H-12H-12C-吖二苯并[cd,mn]芘、4,7-二(9H-咔唑-9-基)-1,10-菲咯啉、2,2'-双(4-(咔唑-9-基)苯基)联苯、2,8-双(二苯基磷酰基)二苯并[b,d]噻吩、双(2-甲基苯基)二苯基硅烷、双[3,5-二(9H-咔唑-9-基)苯基]二苯基硅烷、3,6-双(咔唑-9-基)-9-(2-乙基-己基)-9H-咔唑、3-(二苯基磷酰基)-9-(4-(二苯基磷酰基)苯基)-9H-咔唑、3,6-双[(3,5-二苯基)苯基]-9-苯基咔唑等,通过与发光性掺杂剂一起蒸镀,可以形成发光层。
作为发光性掺杂剂,可列举出3-(2-苯并噻唑基)-7-(二乙氨基)香豆素、2,3,6,7-四氢-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、喹吖酮、N,N'-二甲基-喹吖酮、三(2-苯基吡啶)铱(III)(Ir(ppy)3)、双(2-苯基吡啶)(乙酰丙酮)铱(III)(Ir(ppy)2(acac))、三[2-(对-甲苯基)吡啶]铱(III)(Ir(mppy)3)、9,10-双[N,N-二(对-甲苯基)氨基]蒽、9,10-双[苯基(间-甲苯基)氨基]蒽、双[2-(2-羟苯基)苯并噻唑]锌(II)、N10,N10,N10',N10'-四(对-甲苯基)-9,9'-联蒽-10,10'-二胺、N10,N10,N10',N10'-四苯基-9,9'-联蒽-10,10'-二胺、N10,N10'-二苯基-N10,N10'-二萘基-9,9'-联蒽-10,10'-二胺、4,4'-双(9-乙基-3-咔唑1,2-亚乙烯基)-1,1'-联苯、苝、2,5,8,11-四-叔丁基苝、1,4-双[2-(3-N-乙基咔唑基)乙烯基]苯、4,4'-双[4-(二-对甲苯基氨基)苯乙烯基]联苯、4-(二-对甲苯基氨基)-4'-[(二-对甲苯基氨基)苯乙烯基]茋、双[3,5-二氟-2-(2-吡啶基)苯基-(2-羧基吡啶基)]铱(III)、4,4'-双[4-(二苯基氨基)苯乙烯基]联苯、双(2,4-二氟苯基吡啶)四(1-吡唑基)硼酸铱(III)、N,N'-双(萘-2-基)-N,N'-双(苯基)-三(9,9-二甲基亚芴基)、2,7-双{2-[苯基(间甲苯基)氨基]-9,9-二甲基-芴-7-基}-9,9-二甲基-芴、N-(4-((E)-2-(6((E)-4-(二苯基氨基)苯乙烯基)萘-2-基)乙烯基)苯基)-N-苯基苯胺、fac-铱(III)三(1-苯基-3-甲基苯并咪唑啉-2-亚基-C,C2')、mer-铱(III)三(1-苯基-3-甲基苯并咪唑啉-2-亚基-C,C2')、2,7-双[4-(二苯基氨基)苯乙烯基]-9,9-螺联芴、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)氨基]苯乙烯基苯、1,4-双(4-(9H-咔唑-9-基)苯乙烯基)苯、(E)-6-(4-(二苯基氨基)苯乙烯基)-N,N-二苯基萘-2-胺、双(2,4-二氟苯基吡啶)(5-(吡啶-2-基)-1H-四唑)铱(III)、双(3-三氟甲基-5-(2-吡啶基)吡唑)((2,4-二氟苄基)二苯基次膦酸)铱(III)、双(3-三氟甲基-5-(2-吡啶基)吡唑)(苄基二苯基次膦酸)铱(III)、双(1-(2,4-二氟苄基)-3-甲基苯并咪唑)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑)铱(III)、双(3-三氟甲基-5-(2-吡啶基)吡唑)(4',6'-二氟苯基吡啶)铱(III)、双(4',6'-二氟苯基吡啶)(3,5-双(三氟甲基)-2-(2'-吡啶基)吡咯)铱(III)、双(4',6'-二氟苯基吡啶)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑)铱(III)、(Z)-6-基-N-(6-基喹啉-2(1H)-亚基)喹啉-2-胺-BF2、(E)-2-(2-(4-(二甲氨基)苯乙烯基)-6-甲基-4H-吡喃-4-亚基)丙二腈、4-(二氰基亚甲基)-2-甲基-6-久洛里定基-9-烯基-4H-吡喃、4-(二氰基亚甲基)-2-甲基-6-(1,1,7,7-四甲基久洛里定基-9-烯基)-4H-吡喃、4-(二氰基亚甲基)-2-叔丁基-6-(1,1,7,7-四甲基久洛里定-4-基-乙烯基)-4H-吡喃、三(二苯甲酰基甲烷)菲咯啉铕(III)、5,6,11,12-四苯基并四苯、双(2-苯并[b]噻吩-2-基-吡啶)(乙酰丙酮)铱(III)、三(1-苯基异喹啉)铱(III)、双(1-苯基异喹啉)(乙酰丙酮)铱(III)、双[1-(9,9-二甲基-9H-芴-2-基)-异喹啉](乙酰丙酮)铱(III)、双[2-(9,9-二甲基-9H-芴-2-基)喹啉](乙酰丙酮)铱(III)、三[4,4'-二叔丁基-(2,2')-联吡啶]钌(III)·双(六氟磷酸盐)、三(2-苯基喹啉)铱(III)、双(2-苯基喹啉)(乙酰丙酮)铱(III)、2,8-二叔丁基-5,11-双(4-叔丁基苯基)-6,12-二苯基并四苯、双(2-苯基苯并噻唑)(乙酰丙酮)铱(III)、5,10,15,20-四苯基四苯并卟啉铂、锇(II)双(3-三氟甲基-5-(2-吡啶)-吡唑)二甲基苯基膦、锇(II)双(3-(三氟甲基)-5-(4-叔丁基吡啶基)-1,2,4-三唑)二苯基甲基膦、锇(II)双(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑)二甲基苯基膦、锇(II)双(3-(三氟甲基)-5-(4-叔丁基吡啶基)-1,2,4-三唑)二甲基苯基膦、双[2-(4-正己基苯基)喹啉](乙酰丙酮)铱(III)、三[2-(4-正己基苯基)喹啉]铱(III)、三[2-苯基-4-甲基喹啉]铱(III)、双(2-苯基喹啉)(2-(3-甲基苯基)吡啶)铱(III)、双(2-(9,9-二乙基-芴-2-基)-1-苯基-1H-苯并[d]咪唑)(乙酰丙酮)铱(III)、双(2-苯基吡啶)(3-(吡啶-2-基)-2H-色烯-2-酯基)铱(III)、双(2-苯基喹啉)(2,2,6,6-四甲基庚烷-3,5-二酯基)铱(III)、双(苯基异喹啉)(2,2,6,6-四甲基庚烷-3,5-二酯基)铱(III)、双(4-苯基噻吩并[3,2-c]吡啶-N,C2')乙酰丙酮铱(III)、(E)-2-(2-叔丁基-6-(2-(2,6,6-三甲基-2,4,5,6-四氢-1H-吡咯并[3,2,1-ij]喹啉-8-基)乙烯基)-4H-吡喃-4-亚基)丙二腈、双(3-三氟甲基-5-(1-异喹啉基)吡唑)(甲基二苯基膦)钌、双[(4-正己基苯基)异喹啉](乙酰丙酮)铱(III)、铂(II)八乙基卟吩、双(2-甲基二苯并[f,h]喹喔啉)(乙酰丙酮)铱(III)、三[(4-正己基苯基)氧喹啉]铱(III)等。
作为形成电子传输层/空穴阻断层的材料,可列举出8-羟基喹啉-锂、2,2',2”-(1,3,5-苯并甲苯基)-三(1-苯基-1-H-苯并咪唑)、2-(4-联苯基)5-(4-叔丁基苯基)-1,3,4-二唑、2,9-二甲基-4,7-二苯基-1,10-菲咯啉、4,7-二苯基-1,10-菲咯啉、双(2-甲基-8-羟基喹啉)-4-(苯基苯酚)铝、1,3-双[2-(2,2'-联吡啶-6-基)-1,3,4-二唑-5-基]苯、6,6'-双[5-(联苯-4-基)-1,3,4-二唑-2-基]-2,2'-联吡啶、3-(4-联苯基)-4-苯基-5-叔丁基苯基-1,2,4-三唑、4-(萘-1-基)-3,5-二苯基-4H-1,2,4-三唑、2,9-双(萘-2-基)-4,7-二苯基-1,10-菲咯啉、2,7-双[2-(2,2'-联吡啶-6-基)-1,3,4-二唑-5-基]-9,9-二甲基芴、1,3-双[2-(4-叔丁基苯基)-1,3,4-二唑-5-基]苯、三(2,4,6-三甲基-3-(吡啶-3-基)苯基)硼烷、1-甲基-2-(4-(萘-2-基)苯基)-1H-咪唑并[4,5f][1,10]菲咯啉、2-(萘-2-基)-4,7-二苯基-1,10-菲咯啉、苯基-二芘基氧化膦、3,3',5,5'-四[(间吡啶基)-葑-3-基]联苯、1,3,5-三[(3-吡啶基)-葑-3-基]苯、4,4'-双(4,6-二苯基-1,3,5-三嗪-2-基)联苯、1,3-双[3,5-二(吡啶-3-基)苯基]苯、双(10-羟基苯并[h]喹啉)铍、二苯基双(4-(吡啶-3-基)苯基)硅烷、3,5-二(芘-1-基)吡啶等。
作为形成电子注入层的材料,可列举出氧化锂(Li2O)、氧化镁(MgO)、氧化铝(Al2O3)、氟化锂(LiF)、氟化钠(NaF)、氟化镁(MgF2)、氟化铯(CsF)、氟化锶(SrF2)、三氧化钼(MoO3)、铝、Li(acac)、乙酸锂、苯甲酸锂等。
作为阴极材料,可列举出铝、镁-银合金、铝-锂合金、锂、钠、钾、铯等。
作为形成电子阻断层的材料,可列举出三(苯基吡唑)铱等。
对于使用本发明电荷传输性清漆制作PLED元件的方法,没有特殊限定,可列举出以下的方法。
在上述OLED元件的制作中,不进行空穴传输层、发光层、电子传输层、电子注入层的真空蒸镀操作,而是依次形成空穴传输性高分子层、发光性高分子层,这样可以制作具有由本发明电荷传输性清漆形成的电荷传输性薄膜的PLED元件。
具体而言,在阳极基板上涂布本发明的电荷传输性清漆,采用上述方法制作空穴注入层,再在其上依次形成空穴传输性高分子层、发光性高分子层,进而蒸镀阴极,制成PLED元件。
作为所用的阴极和阳极材料,可以使用与制作上述OLED元件时同样的材料,进行同样的洗涤处理和表面处理。
作为空穴传输性高分子层和发光性高分子层的形成法,可列举出将空穴传输性高分子材料或者发光性高分子材料、或者其中已加入了掺杂剂物质的材料中加入溶剂并使其溶解或均匀分散,分别将其涂布到空穴注入层或者空穴传输性高分子层上之后,通过烘烤来成膜的方法。
作为空穴传输性高分子材料,可列举出聚[(9,9-二己基芴基-2,7-二基)-co-(N,N'-双{对-丁基苯基}-1,4-二氨基亚苯基)]、聚[(9,9-二辛基芴基-2,7-二基)-co-(N,N'-双{对-丁基苯基}-1,1'-亚联苯基-4,4-二胺)]、聚[(9,9-双{1'-戊烯-5'-基}芴基-2,7-二基)-co-(N,N'-双{对-丁基苯基}-1,4-二氨基亚苯基)]、聚[N,N'-双(4-丁基苯基)-N,N'-双(苯基)-联苯胺]-以聚倍半硅氧烷封端、聚[(9,9-二辛基芴基-2,7-二基)-co-(4,4'-(N-(对-丁基苯基))二苯基胺)]等。
作为发光性高分子材料,可列举出聚(9,9-二烷基芴)(PDAF)等聚芴衍生物、聚(2-甲氧基-5-(2'-乙基己氧基)-1,4-亚苯基1,2-亚乙烯基)(MEH-PPV)等聚亚苯基1,2-亚乙烯基衍生物、聚(3-烷基噻吩)(PAT)等聚噻吩衍生物、聚乙烯基咔唑(PVCz)等。
作为溶剂,可列举出甲苯、二甲苯、氯仿等,作为溶解或者均匀分散法,可列举出搅拌、加热搅拌、超声波分散等方法。
对涂布方法没有特殊限定,可列举出喷墨法、喷涂法、浸涂法、旋转涂布法、转印法、辊涂法、刷涂法等。予以说明,涂布操作优选在氮、氩等惰性气体中进行。
作为烘烤方法,可列举出在惰性气体中或者在真空中,用烘箱或者加热板进行加热的方法。
实施例
以下列举出实施例和比较例,更具体地说明本发明,但本发明不限定于下述的实施例。予以说明,所用的装置如下。
(1)基板洗涤:长州产业(株)制基板洗涤装置(减压等离子体方式)
(2)清漆的涂布:Mikasa(株)制旋转涂布机MS-A100
(3)膜厚测定和平坦性评价:(株)小坂研究所制微细形状测定机Surfcorder ET-4000
(4)接触角测定:协和界面化学(株)制接触角计
(5)EL元件的制作:长州产业(株)制多功能蒸镀装置系统C-E2L1G1-N
(6)EL元件的寿命测定(半衰期测定):(株)EHC制有机EL亮度寿命评价系统PEL-105S
[1]电荷传输性清漆的调制
[调制例1]电荷传输性清漆A
在氮气氛中,将按照国际公开第2013/084664号记载的方法合成的由式[1]表示的苯胺衍生物0.137g、按照国际公开第2006/025342号记载的方法合成的由式[2]表示的芳基磺酸0.271g、属于非离子型含氟表面活性剂的Ftergent 251((株)Neos制)0.02g溶解于1,3-二甲基-2-咪唑烷酮6.6g中。向所获溶液中依次加入2,3-丁二醇8.0g、二丙二醇单甲醚5.4g,搅拌,调制电荷传输性清漆A。
[化10]
[调制例2]电荷传输性清漆B
除了使用Ftergent 212M((株)Neos制)代替Ftergent 251以外,其余按照与调制例1同样的方法调制电荷传输性清漆B。
[调制例3]电荷传输性清漆C
除了使用Ftergent 215M((株)Neos制)代替Ftergent 251以外,其余按照与调制例1同样的方法调制电荷传输性清漆C。
[调制例4]电荷传输性清漆D
除了使用Ftergent 250((株)Neos制)代替Ftergent 251以外,其余按照与调制例1同样的方法调制电荷传输性清漆D。
[调制例5]电荷传输性清漆E
除了使用Ftergent 209F((株)Neos制)代替Ftergent 251以外,其余按照与调制例1同样的方法调制电荷传输性清漆E。
[调制例6]电荷传输性清漆F
除了使用Ftergent 222F((株)Neos制)代替Ftergent 251以外,其余按照与调制例1同样的方法调制电荷传输性清漆F。
[调制例7]电荷传输性清漆G
除了使用Ftergent 245F((株)Neos制)代替Ftergent 251以外,其余按照与调制例1同样的方法调制电荷传输性清漆G。
[调制例8]电荷传输性清漆H
除了使用Ftergent 208G((株)Neos制)代替Ftergent 251以外,其余按照与调制例1同样的方法调制电荷传输性清漆H。
[调制例9]电荷传输性清漆I
除了使用Ftergent 240G((株)Neos制)代替Ftergent 251以外,其余按照与调制例1同样的方法调制电荷传输性清漆I。
[调制例10]电荷传输性清漆J
除了使用Ftergent 212P((株)Neos制)代替Ftergent 251以外,其余按照与调制例1同样的方法调制电荷传输性清漆J。
[调制例11]电荷传输性清漆K
除了使用Ftergent 220P((株)Neos制)代替Ftergent 251以外,其余按照与调制例1同样的方法调制电荷传输性清漆K。
[调制例12]电荷传输性清漆L
除了使用Ftergent 228P((株)Neos制)代替Ftergent 251以外,其余按照与调制例1同样的方法调制电荷传输性清漆L。
[比较调制例1]电荷传输性清漆M
除了不使用Ftergent 251以外,按照与调制例1同样的方法调制电荷传输性清漆M。
[调制例13]电荷传输性清漆N
除了使用Ftergent 710FL((株)Neos制)代替Ftergent 251以外,其余按照与调制例1同样的方法调制电荷传输性清漆N。
[调制例14]电荷传输性清漆O
除了使用Ftergent 710FL((株)Neos制)0.04g代替Ftergent 251以外,其余按照与调制例1同样的方法调制电荷传输性清漆O。
[调制例15]电荷传输性清漆P
除了使用Ftergent 710FM((株)Neos制)代替Ftergent 251以外,其余按照与调制例1同样的方法调制电荷传输性清漆P。
[调制例16]电荷传输性清漆Q
除了使用Ftergent 710FM((株)Neos制)0.04g代替Ftergent 251以外,其余按照与调制例1同样的方法调制电荷传输性清漆Q。
[调制例17]电荷传输性清漆R
除了使用Ftergent 710FS((株)Neos制)代替Ftergent 251以外,其余按照与调制例1同样的方法调制电荷传输性清漆R。
[调制例18]电荷传输性清漆S
除了使用Ftergent 710FS((株)Neos制)0.04g代替Ftergent251以外,其余按照与调制例1同样的方法调制电荷传输性清漆S。
[2]像素内平坦性评价
[实施例1-1、比较例1-1]
在使用正性感光性聚酰亚胺制作的带有像素宽度(结构物之间)50×100μm的结构物的ITO基板上,采用旋转涂布法将电荷传输性清漆A~M成膜,在大气中,用加热板在80℃干燥1分钟,在230℃加热烘烤15分钟,制成膜厚30nm的薄膜。用触针式膜厚计测定像素部分的膜的最大段差。结果示于表1。
[表1]
如表1所示,对于未添加非离子型含氟表面活性剂的电荷传输性清漆M,其最大段差为17.4nm,而对于添加了非离子型含氟表面活性剂的电荷传输性清漆A~L,其最大段差变成3nm以下,可以看出,其像素内平坦性显著提高。
[实施例1-2]
在使用正性感光性聚酰亚胺制作的带有像素宽度(结构物之间)50×100μm的结构物的ITO基板上,采用旋转涂布法将电荷传输性清漆N~S成膜,在大气中,用加热板在80℃干燥1分钟,在230℃加热烘烤15分钟,制成膜厚30nm、60nm、100nm的薄膜。用触针式膜厚计测定像素部分的膜的最大段差。结果示于表2。
[表2]
如表2所示,对于添加了非离子型含氟表面活性剂的电荷传输性清漆N~S,当膜厚为30~100nm时,最大段差变成3nm以下,可以看出,其像素内平坦性显著提高。
[3]接触角评价
[实施例2-1、比较例2-1]
在设置ITO基板上,采用旋转涂布法将电荷传输性清漆A~M成膜,在大气中,用加热板在80℃干燥1分钟,在230℃加热烘烤15分钟,制成膜厚30nm的薄膜。测定环己基苯(CHB)和3-苯氧基甲苯(3PT)对于所获薄膜的接触角。结果示于表3。
[表3]
如表3所示,由添加了非离子型含氟表面活性剂的电荷传输性清漆A~L制成的薄膜上的接触角,与由未添加非离子型含氟表面活性剂的电荷传输性清漆M制成的薄膜上的接触角相比没有变化,可以看出,所添加的表面活性剂对表层的润湿性没有不良影响。
[实施例2-2]接触角评价
在设置ITO基板上,采用旋转涂布法将电荷传输性清漆N~S成膜,在大气中,用加热板在80℃干燥1分钟,在230℃加热烘烤15分钟,制成膜厚30nm、60nm、100nm的薄膜。测定环己基苯(CHB)对于所获薄膜的接触角。结果示于表4。
[表4]
如表4所示,当膜厚为30~100nm时,由添加了非离子型含氟表面活性剂的电荷传输性清漆N~S制成的薄膜上的接触角全部在5°以下,可以看出,所添加的表面活性剂对于表层涂布时的润湿性没有不良影响。
[4]有机EL元件(OLED元件)的制作及其特性评价
作为评价电学特性时的基板,使用氧化铟锡在表面上形成了膜厚150nm的图案的25mm×25mm×0.7t的玻璃基板(以下简写为ITO基板)。对于ITO基板,先用O2等离子体洗涤装置(150W、30秒钟)除去表面上的杂质后再使用。
[实施例3-1]使用电荷传输性清漆A制作OLED元件
使用旋转涂布机将调制例1中制得的电荷传输性清漆A涂布到ITO基板上,然后,在80℃干燥1分钟,再在230℃烘烤15分钟,在ITO基板上形成35nm的均匀薄膜。
接着,使用蒸镀装置(真空度1.0×10-5Pa),在形成了薄膜的ITO基板上,依次叠层N,N′-二(1-萘基)-N,N′-二苯基联苯胺(α-NPD)、三(8-羟基喹啉)铝(III)(Alq3)、氟化锂、以及铝的薄膜,得到OLED元件。此时,按照Alq3和铝各自的蒸镀速率均为0.2nm/秒、氟化锂的蒸镀速率为0.02nm/秒的条件进行,膜厚分别为30nm、40nm、0.5nm和100nm。
予以说明,为了防止由于空气中的氧、水等的影响所导致的特性劣化,利用密封基板将OLED元件密封后,评价其特性。密封按以下的顺序进行。
在氧浓度2ppm以下、露点-85℃以下的氮气氛中,将有机EL元件置于密封基板之间,将密封基板用胶粘剂(Nagase Chemtex(株)制,XNR5516Z-B1)贴合。此时,将干燥剂(Dynic株)制,HD-071010W-40)与OLED元件一起置于密封基板内。
向贴合了的密封基板照射UV光(波长:365nm、照射量:6000mJ/cm2),然后,在80℃退火处理1小时,使胶粘剂固化。
[实施例3-2]使用电荷传输性清漆B制作OLED元件
除了使用调制例2中制得的电荷传输性清漆B代替电荷传输性清漆A以外,其余按照与实施例3-1同样的方法制作OLED元件。
[实施例3-3]使用电荷传输性清漆C制作OLED元件
除了使用调制例3中制得的电荷传输性清漆C代替电荷传输性清漆A以外,其余按照与实施例3-1同样的方法制作OLED元件。
[实施例3-4]使用电荷传输性清漆D制作OLED元件
除了使用调制例4中制得的电荷传输性清漆D代替电荷传输性清漆A以外,其余按照与实施例3-1同样的方法制作OLED元件。
[实施例3-5]使用电荷传输性清漆E制作OLED元件
除了使用调制例5中制得的电荷传输性清漆E代替电荷传输性清漆A以外,其余按照与实施例3-1同样的方法制作OLED元件。
[实施例3-6]使用电荷传输性清漆F制作OLED元件
除了使用调制例6中制得的电荷传输性清漆F代替电荷传输性清漆A以外,其余按照与实施例3-1同样的方法制作OLED元件。
[实施例3-7]使用电荷传输性清漆G制作OLED元件
除了使用调制例7中制得的电荷传输性清漆G代替电荷传输性清漆A以外,其余按照与实施例3-1同样的方法制作OLED元件。
[实施例3-8]使用电荷传输性清漆H制作OLED元件
除了使用调制例8中制得的电荷传输性清漆H代替电荷传输性清漆A以外,其余按照与实施例3-1同样的方法制作OLED元件。
[实施例3-9]使用电荷传输性清漆I制作OLED元件
除了使用调制例9中制得的电荷传输性清漆I代替电荷传输性清漆A以外,其余按照与实施例3-1同样的方法制作OLED元件。
[实施例3-10]使用电荷传输性清漆J制作OLED元件
除了使用调制例10中制得的电荷传输性清漆J代替电荷传输性清漆A以外,其余按照与实施例3-1同样的方法制作OLED元件。
[实施例3-11]使用电荷传输性清漆K制作OLED元件
除了使用调制例11中制得的电荷传输性清漆K代替电荷传输性清漆A以外,其余按照与实施例3-1同样的方法制作OLED元件。
[实施例3-12]使用电荷传输性清漆L制作OLED元件
除了使用调制例12中制得的电荷传输性清漆L代替电荷传输性清漆A以外,其余按照与实施例3-1同样的方法制作OLED元件。
[实施例3-13]使用电荷传输性清漆N制作OLED元件
除了使用调制例13中制得的电荷传输性清漆N代替电荷传输性清漆A以外,其余按照与实施例3-1同样的方法制作OLED元件。
[实施例3-14]使用电荷传输性清漆O制作OLED元件
除了使用调制例14中制得的电荷传输性清漆O代替电荷传输性清漆A以外,其余按照与实施例3-1同样的方法制作OLED元件。
[实施例3-15]使用电荷传输性清漆P制作OLED元件
除了使用调制例15中制得的电荷传输性清漆P代替电荷传输性清漆A以外,其余按照与实施例3-1同样的方法制作OLED元件。
[实施例3-16]使用电荷传输性清漆Q制作OLED元件
除了使用调制例16中制得的电荷传输性清漆Q代替电荷传输性清漆A以外,其余按照与实施例3-1同样的方法制作OLED元件。
[实施例3-17]使用电荷传输性清漆R制作OLED元件
除了使用调制例17中制得的电荷传输性清漆R代替电荷传输性清漆A以外,其余按照与实施例3-1同样的方法制作OLED元件。
[实施例3-18]使用电荷传输性清漆S制作OLED元件
除了使用调制例18中制得的电荷传输性清漆S代替电荷传输性清漆A以外,其余按照与实施例3-1同样的方法制作OLED元件。
[比较例3-1]使用电荷传输性清漆M制作OLED元件
除了使用比较调制例1中制得的电荷传输性清漆M代替电荷传输性清漆A以外,其余按照与实施例3-1同样的方法制作OLED元件。
测定实施例3-1~3-18和比较例3-1中制得的OLED元件在亮度5000cd/m2时的电压、电流密度和电流效率、以及亮度的半衰期(初期亮度5000cd/m2)。结果示于表5。
[表5]
如表5所示,在清漆中添加了非离子型含氟表面活性剂的实施例3-1~3-18的元件,与未添加的比较例3-1的元件相比,其初期特性和半衰期寿命没有很大的区别,可以看出,所添加的非离子型含氟表面活性剂对元件特性没有影响。
Claims (11)
1.电荷传输性清漆,其含有电荷传输性物质、非离子型含氟表面活性剂、有机溶剂和掺杂剂物质;其特征在于,
上述非离子型含氟表面活性剂具有含全氟烯基的全氟烃结构和氧化烯结构,
上述掺杂剂物质包含选自杂多酸和分子量为2000以下的芳基磺酸化合物中的至少一种,
上述非离子型含氟表面活性剂由式(A1)~(A3)的任一个表示:
Rf-O-(A0O)n-R0 (A1)
Rf-O-(A0O)n-Rf (A2)
R0-(OA0)n-O-Rf-O-(A0O)n-R0 (A3)
式中,Rf相互独立地表示含全氟烯基的全氟烃结构;R0相互独立地表示氢原子或者碳数1~20的烷基;A0表示碳数2~10的亚烷基,n表示2~50的整数。
2.权利要求1所述的电荷传输性清漆,其中,上述全氟烯基为支链状全氟烯基。
4.权利要求1所述的电荷传输性清漆,其中,A0为亚乙基。
6.权利要求1所述的电荷传输性清漆,其中,上述电荷传输性物质由下述式(4)表示:
式(4)中,X1表示-NY1-、-O-、-S-、或者-(CR8R9)L-,当m1或m2为0时,表示-NY1-;
Y1相互独立地表示氢原子、可被Z7取代的、碳数1~20的烷基、碳数2~20的烯基或者碳数2~20的炔基、或者可被Z8取代的、碳数6~20的芳基或者碳数2~20的杂芳基;
R8和R9相互独立地表示氢原子、卤原子、硝基、氰基、氨基、醛基、羟基、硫醇基、磺酸基、羧酸基、可被Z7取代的、碳数1~20的烷基、碳数2~20的烯基或者碳数2~20的炔基、可被Z8取代的、碳数6~20的芳基或者碳数2~20的杂芳基、或者-NHY2、-NY3Y4、-C(O)Y5、-OY6、-SY7、-SO3Y8、-C(O)OY9、-OC(O)Y10、-C(O)NHY11或者C(O)NY12Y13基;
L表示由-(CR8R9)-表示的2价亚烷基的重复单元数,为1~20的整数;
R2~R5相互独立地表示氢原子、卤原子、硝基、氰基、氨基、醛基、羟基、硫醇基、磺酸基、羧酸基、可被Z7取代的、碳数1~20的烷基、碳数2~20的烯基或者碳数2~20的炔基、可被Z8取代的、碳数6~20的芳基或者碳数2~20的杂芳基、或者-NHY2、-NY3Y4、-C(O)Y5、-OY6、-SY7、-SO3Y8、-C(O)OY9、-OC(O)Y10、-C(O)NHY11或者C(O)NY12Y13;
R6和R7表示氢原子、卤原子、可被Z7取代的碳数1~10的烷基、可被Z8取代的碳数6~14的芳基、或者可被Z8取代的二苯基氨基;
Y2~Y13相互独立地表示可被Z7取代的、碳数1~20的烷基、碳数2~20的烯基或者碳数2~20的炔基、或者可被Z8取代的、碳数6~20的芳基或者碳数2~20的杂芳基;
Z7为卤原子、硝基、氰基、氨基、醛基、羟基、硫醇基、磺酸基、羧酸基、或者可被Z9取代的、碳数6~20的芳基或者碳数2~20的杂芳基;
Z8为卤原子、硝基、氰基、氨基、醛基、羟基、硫醇基、磺酸基、羧酸基、或者可被Z9取代的、碳数1~20的烷基、碳数2~20的烯基或者碳数2~20的炔基;
Z9为卤原子、硝基、氰基、氨基、醛基、羟基、硫醇基、磺酸基、或者羧酸基;
m1和m2相互独立地表示0以上的整数,且满足1≤m1+m2≤20。
7.电荷传输性薄膜,其是使用权利要求1~6的任1项所述的电荷传输性清漆制作的。
8.电子器件,其具有权利要求7所述的电荷传输性薄膜。
9.有机电致发光元件,其具有权利要求7所述的电荷传输性薄膜。
10.权利要求9所述的有机电致发光元件,其中,上述电荷传输性薄膜构成空穴注入层。
11.电荷传输性薄膜的制造方法,其特征在于,将权利要求1~6的任1项所述的电荷传输性清漆涂布到基材上,并使溶剂蒸发。
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