CN107428676B - 苯胺衍生物及其利用 - Google Patents
苯胺衍生物及其利用 Download PDFInfo
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- CN107428676B CN107428676B CN201680011898.XA CN201680011898A CN107428676B CN 107428676 B CN107428676 B CN 107428676B CN 201680011898 A CN201680011898 A CN 201680011898A CN 107428676 B CN107428676 B CN 107428676B
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- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title claims abstract 4
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- 239000002253 acid Substances 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
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- 125000005843 halogen group Chemical group 0.000 description 43
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- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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- AFBMXTJJCXKVRZ-UHFFFAOYSA-N dimethyl(phenyl)phosphane osmium(2+) 2-[5-(trifluoromethyl)-1H-1,2,4-triazol-3-yl]pyridine Chemical compound [Os+2].CP(C)C1=CC=CC=C1.FC(F)(F)C1=NNC(C=2N=CC=CC=2)=N1.FC(F)(F)C1=NNC(C=2N=CC=CC=2)=N1 AFBMXTJJCXKVRZ-UHFFFAOYSA-N 0.000 description 1
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- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
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- CJMZLCRLBNZJQR-UHFFFAOYSA-N ethyl 2-amino-4-(4-fluorophenyl)thiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC=C1C1=CC=C(F)C=C1 CJMZLCRLBNZJQR-UHFFFAOYSA-N 0.000 description 1
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- HTSRFYSEWIPFNI-UHFFFAOYSA-N ethyl-dimethoxy-methylsilane Chemical compound CC[Si](C)(OC)OC HTSRFYSEWIPFNI-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
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- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- VRINOTYEGADLMW-UHFFFAOYSA-N heptyl(trimethoxy)silane Chemical compound CCCCCCC[Si](OC)(OC)OC VRINOTYEGADLMW-UHFFFAOYSA-N 0.000 description 1
- RSKGMYDENCAJEN-UHFFFAOYSA-N hexadecyl(trimethoxy)silane Chemical compound CCCCCCCCCCCCCCCC[Si](OC)(OC)OC RSKGMYDENCAJEN-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
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- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 1
- BNASDYJRNOLPQY-UHFFFAOYSA-N iridium 2-phenylquinoline Chemical compound [Ir].c1ccc(cc1)-c1ccc2ccccc2n1.c1ccc(cc1)-c1ccc2ccccc2n1.c1ccc(cc1)-c1ccc2ccccc2n1 BNASDYJRNOLPQY-UHFFFAOYSA-N 0.000 description 1
- QTRRAHGRSMFAKW-UHFFFAOYSA-N iridium(3+);1-phenylpyrazole Chemical compound [Ir+3].C1=CC=NN1C1=CC=CC=[C-]1.C1=CC=NN1C1=CC=CC=[C-]1.C1=CC=NN1C1=CC=CC=[C-]1 QTRRAHGRSMFAKW-UHFFFAOYSA-N 0.000 description 1
- BFBVQPCWYPBWEY-UHFFFAOYSA-N iridium(3+);pentane-2,4-dione;2-phenylpyridine Chemical compound [Ir+3].CC(=O)CC(C)=O.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 BFBVQPCWYPBWEY-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
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- 229910052746 lanthanum Inorganic materials 0.000 description 1
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- 239000002346 layers by function Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
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- COLNWNFTWHPORY-UHFFFAOYSA-M lithium;8-hydroxyquinoline-2-carboxylate Chemical compound [Li+].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 COLNWNFTWHPORY-UHFFFAOYSA-M 0.000 description 1
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- 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
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- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
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- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 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
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
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- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
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- 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
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Classifications
-
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Abstract
本发明提供太阳能电池组件和太阳能电池组件的制造方法。例如由下述式表示的苯胺衍生物对于有机溶剂的溶解性良好,同时在将包含它们作为电荷传输性物质的薄膜应用于空穴注入层的情况下能够得到具有优异的寿命特性的有机EL元件。
Description
技术领域
本发明涉及苯胺衍生物及其利用。
背景技术
在有机电致发光(以下称为有机EL)元件中,作为发光层、电荷注入层,使用由有机化合物构成的电荷传输性薄膜。特别地,空穴注入层承担阳极与空穴传输层或发光层的电荷的授受,为了实现有机EL元件的低电压驱动和高亮度而发挥重要的功能。
空穴注入层的形成方法大致分为以蒸镀法为代表的干法和以旋涂法为代表的湿法,将这些各方法进行比较时,湿法能够大面积地高效率地制造平坦性高的薄膜。因此,在有机EL显示器的大面积化不断发展的现今,希望可采用湿法形成的空穴注入层。
鉴于这样的实际情况,本发明人已开发出可适用于各种湿法、同时提供在应用于有机EL元件的空穴注入层的情况下能够实现优异的EL元件特性的薄膜的电荷传输性材料、用于其的对于有机溶剂的溶解性良好的化合物(例如参照专利文献1~4)。
现有技术文献
专利文献
专利文献1:国际公开第2008/032616号
专利文献2:国际公开第2008/129947号
专利文献3:国际公开第2006/025342号
专利文献4:国际公开第2010/058777号
发明内容
发明要解决的课题
本发明也与目前为止开发的上述专利文献的技术同样地,目的在于提供显示在有机溶剂中的良好的溶解性、同时薄膜化而应用于空穴注入层的情况下能够实现具有优异的寿命特性的有机EL元件的苯胺衍生物。
用于解决课题的手段
本发明人为了实现上述目的反复锐意研究,结果发现:规定的苯胺衍生物具有在有机溶剂中的优异的溶解性,由使其在有机溶剂中溶解而制备的清漆得到发挥高电荷传输性的薄膜,以及在将该薄膜应用于有机EL元件的空穴注入层的情况下得到高寿命的元件,完成了本发明。
即,本发明提供
1.苯胺衍生物,其特征在于,由式(1)表示,
[化1]
[式中,Ph1表示由式(P1)表示的基团,
[化2]
(式中,R1~R4相互独立地表示氢原子、卤素原子、硝基、氰基、或者可被卤素原子取代的、碳数1~20的烷基、碳数2~20的烯基、碳数2~20的炔基、碳数6~20的芳基或碳数2~20的杂芳基。)Ar1相互独立地表示由式(A1)~(A34)表示的任一个基团,
[化3]
[化4]
[化5]
[化6]
(式中,R5~R582相互独立地表示氢原子、卤素原子、硝基、氰基、或者可被卤素原子取代的、二苯基氨基、碳数1~20的烷基、碳数2~20的烯基、碳数2~20的炔基、碳数6~20的芳基或碳数2~20的杂芳基,Ar2相互独立地表示可被二(碳数6~20的芳基)氨基取代的碳数6~20的芳基,R583表示氢原子、可被Z1取代的、碳数1~20的烷基、碳数2~20的烯基或碳数2~20的炔基、或者可被Z4取代的、碳数6~20的芳基或碳数2~20的杂芳基,R584和R585相互独立地表示可被Z4取代的、碳数6~20的芳基或碳数2~20的杂芳基,Z1表示卤素原子、硝基、氰基、或者可被Z2取代的、碳数6~20的芳基或碳数2~20的杂芳基,Z2表示卤素原子、硝基、氰基、或者可被Z3取代的、碳数1~20的烷基、碳数2~20的烯基或碳数2~20的炔基,Z3表示卤素原子、硝基或氰基,Z4表示卤素原子、硝基、氰基、或者可被Z5取代的、碳数1~20的烷基、碳数2~20的烯基或碳数2~20的炔基,Z5表示卤素原子、硝基、氰基、或者可被Z3取代的、碳数6~20的芳基或碳数2~20的杂芳基,k表示2~10的整数。)]
2. 1的苯胺衍生物,其中,上述R1~R4全部为氢原子,
3. 1或2的苯胺衍生物,其中,上述R5~R582全部为氢原子,
4.电荷传输性物质,其由1~3的任一项的苯胺衍生物构成,
5.电荷传输性材料,其包含4的电荷传输性物质,
6.电荷传输性清漆,其包含4的电荷传输性物质和有机溶剂,
7. 6的电荷传输性清漆,其还包含掺杂剂物质,
8. 7的电荷传输性清漆,其中,上述掺杂剂物质为芳基磺酸化合物,
9.使用6~8的任一项的电荷传输性清漆制作的电荷传输性薄膜,
10.有机电致发光元件,其具有9的电荷传输性薄膜,
11.电荷传输性薄膜的制造方法,其特征在于,在基材上涂布6~8的任一项的电荷传输性清漆,使溶剂蒸发。
发明的效果
本发明的苯胺衍生物易溶于有机溶剂,使其与掺杂剂一起溶解于有机溶剂,能够容易地制备电荷传输性清漆。
由本发明的电荷传输性清漆制作的薄膜显示高电荷传输性,因此能够适宜地用作以有机EL元件为首的电子器件用薄膜。特别地,通过将该薄膜应用于有机EL元件的空穴注入层,能够得到寿命特性优异的有机EL元件。
另外,本发明的电荷传输性清漆即使在使用了旋涂法、狭缝式涂布法等可大面积地成膜的各种湿法的情况下也能够再现性良好地制造电荷传输性优异的薄膜,因此对于近年来的有机EL元件的领域中的进展也能够充分地应对。
具体实施方式
以下对本发明进一步详细地说明。
本发明涉及的苯胺衍生物由式(1)表示。
[化7]
上述式(1)中的Ph1表示由式(P1)表示的基团。
[化8]
其中,R1~R4相互独立地表示氢原子、卤素原子、硝基、氰基、或者可被卤素原子取代的、碳数1~20的烷基、碳数2~20的烯基、碳数2~20的炔基、碳数6~20的芳基或碳数2~20的杂芳基。
作为卤素原子,可列举出氟原子、氯原子、溴原子、碘原子等。
作为碳数1~20的烷基,直链状、分支链状、环状的烷基均可,例如可列举出甲基、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的直链或分支链状烷基;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。
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-噁唑基、4-噁唑基、5-噁唑基、3-异噁唑基、4-异噁唑基、5-异噁唑基、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。
特别地,作为R1~R4,优选氢原子、氟原子、氰基、可被卤素原子取代的碳数1~20的烷基、可被卤素原子取代的碳数6~20的芳基、可被卤素原子取代的碳数2~20的杂芳基,更优选氢原子、氟原子、氰基、可被卤素原子取代的碳数1~10的烷基、可被卤素原子取代的苯基,进一步优选氢原子、氟原子,最优选氢原子。
以下列举出作为Ph1优选的基团的具体例,但并不限定于此。
[化9]
式(1)中的Ar1相互独立地表示由上述式(A1)~(A34)表示的任一个基团。
特别地,对于式(A1)~(A26)和(A29)~(A34),优选由下述式(A1′)~(A26′)和(A29′)~(A34′)表示的基团。
其中,如果考虑该苯胺化合物的在有机溶剂中的溶解性和得到的薄膜的电荷传输性的平衡,则优选(A1′)、(A2′)、(A25′)、(A26′)、(A29′),更优选(A1′)、(A2′)、(A29′)。
另外,如上述那样,式(1)中的Ar1相互独立地表示由上述式(A1)~(A34)表示的任一个基团,但从化合物的合成的容易性等的观点出发,优选式(1)中的2个Ar1为同一基团。
[化10]
[化11]
[化12]
[化13]
上述R5~R582相互独立地表示氢原子、卤素原子、硝基、氰基、或者可被卤素原子取代的、二苯基氨基、碳数1~20的烷基、碳数2~20的烯基、碳数2~20的炔基、碳数6~20的芳基或碳数2~20的杂芳基,R583表示氢原子、可被Z1取代的、碳数1~20的烷基、碳数2~20的烯基或碳数2~20的炔基、或者可被Z4取代的、碳数6~20的芳基或碳数2~20的杂芳基,R584和R585相互独立地表示可被Z4取代的、碳数6~20的芳基或碳数2~20的杂芳基,Z1表示卤素原子、硝基、氰基、或者可被Z2取代的、碳数6~20的芳基或碳数2~20的杂芳基,Z2表示卤素原子、硝基、氰基、或者可被Z3取代的、碳数1~20的烷基、碳数2~20的烯基或碳数2~20的炔基,Z3表示卤素原子、硝基或氰基,Z4表示卤素原子、硝基、氰基、或者可被Z5取代的、碳数1~20的烷基、碳数2~20的烯基或碳数2~20的炔基,Z5表示卤素原子、硝基、氰基、或者可被Z3取代的、碳数6~20的芳基或碳数2~20的杂芳基。
作为这些卤素原子、碳数1~20的烷基、碳数2~20的烯基、碳数2~20的炔基、碳数6~20的芳基和碳数2~20的杂芳基的具体例,可列举出与上述R1和R2中说明的具体例同样的具体例。
特别地,作为R5~R582,优选氢原子、氟原子、氰基、可被卤素原子取代的二苯基氨基、可被卤素原子取代的碳数1~20的烷基、可被卤素原子取代的碳数6~20的芳基、可被卤素原子取代的碳数2~20的杂芳基,更优选氢原子、氟原子、氰基、可被卤素原子取代的碳数1~10的烷基、可被卤素原子取代的苯基,进一步优选氢原子、氟原子、甲基、三氟甲基,最优选氢原子。
作为R583,优选氢原子、可被Z4取代的碳数6~20的芳基、可被Z4取代的碳数2~20的杂芳基、可被Z1取代的碳数1~20的烷基,更优选氢原子、可被Z4取代的碳数6~14的芳基、可被Z4取代的碳数2~14的杂芳基、可被Z1取代的碳数1~10的烷基,进一步优选氢原子、可被Z4取代的碳数6~14的芳基、可被Z4取代的碳数2~14的含氮杂芳基、可被Z1取代的碳数1~10的烷基,进一步优选氢原子、可被Z4取代的苯基、可被Z4取代的1-萘基、可被Z4取代的2-萘基、可被Z4取代的2-吡啶基、可被Z4取代的3-吡啶基、可被Z4取代的4-吡啶基、可被Z1取代的甲基。
作为R584和R585,优选可被Z4取代的碳数6~14的芳基、可被Z4取代的碳数2~14的杂芳基,更优选可被Z4取代的碳数6~14的芳基,进一步优选可被Z4取代的苯基、可被Z4取代的1-萘基、可被Z4取代的2-萘基。
再有,R583中,取代基Z1优选卤素原子或可被Z2取代的碳数6~20的芳基,更优选卤素原子或可被Z2取代的苯基,最优选不存在(即,为未取代)。
R584和R585中,取代基Z4优选卤素原子或可被Z5取代的碳数1~20的烷基,更优选卤素原子或可被Z5取代的碳数1~4的烷基,最优选不存在(即,为未取代)。
而且,Z2、Z3和Z5优选卤素原子,更优选氟,最优选不存在(即,为未取代)。
上述Ar2相互独立地表示可被二(碳数6~20的芳基)氨基取代的碳数6~20的芳基。
作为碳数6~20的芳基的具体例,可列举出与上述R1中说明的具体例同样的具体例,作为二(碳数6~20的芳基)氨基的具体例,可列举出二苯基氨基、1-萘基苯基氨基、二(1-萘基)氨基、1-萘基-2-萘基氨基、二(2-萘基)氨基等。
作为Ar2,优选苯基、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、对-(二苯基氨基)苯基、对-(1-萘基苯基氨基)苯基、对-(二(1-萘基)氨基)苯基、对-(1-萘基-2-萘基氨基)苯基、对-(二(2-萘基)氨基)苯基,更优选对-(二苯基氨基)苯基。
以下列举出作为Ar1优选的基团的具体例,但并不限定于这些。
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(式中,R583表示与上述相同的含义。)
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本发明中,作为优选作为R583的基团的具体例,可列举出以下的基团,但并不限定于这些。
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上述式(1)中的k表示2~10的整数,但从提高化合物的在有机溶剂中的溶解性的观点出发,优选2~5,更优选2~4,进一步优选2或3。
本发明中,上述烷基、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,上述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。
本发明的由式(1)表示的苯胺衍生物能够通过在催化剂存在下使由式(2)表示的二胺化合物与由式(3)表示的芳基化合物反应而制造。
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(式中,X表示卤素原子或准卤素基团,Ar1、Ph1和k表示与上述相同的含义。)
作为卤素原子,可列举出与上述同样的卤素原子。
作为准卤素基团,可列举出甲磺酰氧基、三氟甲磺酰氧基、九氟丁磺酰氧基等(氟)烷基磺酰氧基;苯磺酰氧基、甲苯磺酰氧基等芳香族磺酰氧基等。
对于由式(2)表示的二胺化合物与由式(3)表示的芳基化合物的进料比而言,相对于二胺化合物的末端NH2基的物质量,优选芳基化合物为1~1.2当量左右。
作为上述反应中使用的催化剂,例如可列举出氯化铜、溴化铜、碘化铜等铜催化剂;Pd(PPh3)4(四(三苯基膦)钯)、Pd(PPh3)2Cl2(双(三苯基膦)二氯钯)、Pd(dba)2(双(亚苄基丙酮)钯)、Pd2(dba)3(三(亚苄基丙酮)二钯)、Pd(P-t-Bu3)2(双(三(叔-丁基)膦)钯)、Pd(OAc)2(醋酸钯)等钯催化剂等。这些催化剂可单独地使用,也可将2种以上组合使用。另外,这些催化剂可与公知的适当的配体一起使用。
作为这样的配体,可列举出三苯基膦、三-邻-甲苯基膦、二苯基甲基膦、苯基二甲基膦、三甲基膦、三乙基膦、三丁基膦、三-叔-丁基膦、二-叔-丁基(苯基)膦、二-叔-丁基(4-二甲基氨基苯基)膦、1,2-双(二苯基膦基)乙烷、1,3-双(二苯基膦基)丙烷、1,4-双(二苯基膦基)丁烷、1,1’-双(二苯基膦基)二茂铁等叔膦、亚磷酸三甲酯、亚磷酸三乙酯、亚磷酸三苯酯等亚磷酸三酯等。
就催化剂的使用量而言,相对于由式(3)表示的芳基化合物1mol,可以设为0.2mol左右,优选0.15mol左右。
另外,在使用配体的情况下,就其使用量而言,相对于使用的金属络合物,可以设为0.1~5当量,优选1~2当量。
原料化合物全部为固体的情况下或者从高效率地得到目标的苯胺衍生物的观点出发,上述各反应在溶剂中进行。在使用溶剂的情况下,其种类只要不对反应产生不良影响,则并无特别限制。作为具体例,可列举出脂肪族烃类(戊烷、正己烷、正辛烷、正癸烷、十氢萘等)、卤代脂肪族烃类(氯仿、二氯甲烷、二氯乙烷、四氯化碳等)、芳香族烃类(苯、硝基苯、甲苯、邻二甲苯、间二甲苯、对二甲苯、均三甲基苯等)、卤代芳香族烃类(氯苯、溴苯、邻二氯苯、间二氯苯、对二氯苯等)、醚类(二乙醚、二异丙醚、叔丁基甲基醚、四氢呋喃、二噁烷、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷等)、酮类(丙酮、甲乙酮、甲基异丁基酮、二正丁基酮、环己酮等)、酰胺类(N,N-二甲基甲酰胺、N,N-二甲基乙酰胺等)、内酰胺和内酯类(N-甲基吡咯烷酮、γ-丁内酯等)、脲类(N,N-二甲基咪唑啉酮、四甲基脲等)、亚砜类(二甲基亚砜、环丁砜等)、腈类(乙腈、丙腈、丁腈等)等,这些溶剂可单独使用,也可将2种以上混合使用。
反应温度可在使用的溶剂的熔点到沸点的范围内适当地设定,特别地,优选0~200℃左右,更优选20~150℃。
反应结束后,按照常规方法进行后处理,能够得到目标的苯胺衍生物。
以下列举出由式(1)表示的苯胺衍生物的具体例,但并不限定于这些。应予说明,表的“2个Ar1”、“Ph1”、“k”和“R583”表示与各行中所示的各化合物有关的式(1)中的规定,例如由式(E1)表示的化合物、由式(E145)表示的化合物分别如下所述。
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[表1]
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本发明的电荷传输性清漆包括包含由式(1)表示的苯胺衍生物的电荷传输性物质和有机溶剂,根据得到的薄膜的用途,以其电荷传输能力的提高等为目的,可包含掺杂剂物质。
作为掺杂剂物质,只要是在清漆中使用的至少一种的溶剂中溶解的掺杂剂物质,则并无特别限定,无机系的掺杂剂物质、有机系的掺杂剂物质都能够使用。
另外,无机系和有机系的掺杂剂物质可1种单独地使用,也可将2种以上组合使用。
作为掺杂剂物质的具体例,可列举出苯磺酸、甲苯磺酸、樟脑磺酸、羟基苯磺酸、5-磺基水杨酸、十二烷基苯磺酸、聚苯乙烯磺酸、国际公开第2005/000832号中记载的1,4-苯并二噁烷二磺酸化合物、国际公开第2006/025342号中记载的芳基磺酸化合物、日本特开2005-108828号公报中记载的二壬基萘磺酸化合物等有机强酸;国际公开第2010/058777号中记载的磷钼酸、磷钨酸、磷钨钼酸等杂多酸等无机氧化剂等,可将它们各自组合使用。
其中,优选芳基磺酸化合物,作为其具体例,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-苯并二噁烷二磺酸化合物、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等。
作为优选作为本发明中的掺杂剂物质的芳基磺酸化合物的例子,可列举出由式(4)或(5)表示的芳基磺酸化合物。
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A1表示O或S,优选O。
A2表示萘环或蒽环,优选萘环。
A3表示2~4价的全氟联苯基,p表示A1与A3的键合数,是满足2≦p≦4的整数,优选地,A3为全氟亚联苯基,优选为全氟联苯-4,4’-二基,并且p为2。
q表示与A2键合的磺酸基数,是满足1≦q≦4的整数,最优选2。
A4~A8相互独立地表示氢原子、卤素原子、氰基、碳数1~20的烷基、碳数1~20的卤代烷基、或碳数2~20的卤代烯基,但A4~A8中至少3个为卤素原子。
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,作为卤素原子、碳数1~20的烷基的例子,可列举出与上述同样的例子,作为卤素原子,优选氟原子。
这些中,A4~A8优选为氢原子、卤素原子、氰基、碳数1~10的烷基、碳数1~10的卤代烷基、或碳数2~10的卤代烯基,并且A4~A8中至少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、或碳数2~5的氟代烯基,并且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、或碳数1~5的全氟烯基,并且A4、A5和A8为氟原子。
应予说明,全氟烷基是将烷基的全部氢原子取代为氟原子的基团,作为全氟烯基,是将烯基的全部氢原子取代为氟原子的基团。
r表示与萘环键合的磺酸基数,是满足1≦r≦4的整数,优选2~4,最优选2。
对作为掺杂剂物质使用的芳基磺酸化合物的分子量并无特别限定,如果考虑与本发明的苯胺衍生物一起使用的情况下的在有机溶剂中的溶解性,优选为2000以下,更优选为1500以下。
以下列举出优选的芳基磺酸化合物的具体例,但并不限定于这些。
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就本发明的电荷传输性清漆中的芳基磺酸化合物的含量而言,相对于由式(1)表示的该苯胺衍生物,优选为0.1~10当量,更优选为0.5~5当量,进一步优选为0.8~3当量。
芳基磺酸化合物可使用市售品,也能够采用国际公开第2006/025342号、国际公开第2009/096352号等中记载的公知的方法合成。
进而,将得到的薄膜用作有机EL元件的空穴注入层的情况下,如果考虑再现性良好地得到高寿命的元件,本发明的电荷传输性清漆优选包含有机硅烷化合物。
作为有机硅烷化合物,可列举出二烷氧基硅烷化合物、三烷氧基硅烷化合物或四烷氧基硅烷化合物,这些可单独地使用,也可将2种以上组合使用。
特别地,作为有机硅烷化合物,优选二烷氧基硅烷化合物或三烷氧基硅烷化合物,更优选三烷氧基硅烷化合物。
以下列举出本发明中可使用的有机硅烷化合物的具体例,但并不限定于这些。
作为二烷氧基硅烷化合物的具体例,可列举出二甲基二甲氧基硅烷、二甲基二乙氧基硅烷、甲基乙基二甲氧基硅烷、二乙基二甲氧基硅烷、二乙基二乙氧基硅烷、甲基丙基二甲氧基硅烷、甲基丙基二乙氧基硅烷、二异丙基二甲氧基硅烷、苯基甲基二甲氧基硅烷、乙烯基甲基二甲氧基硅烷、3-缩水甘油氧基丙基甲基二甲氧基硅烷、3-缩水甘油氧基丙基甲基二乙氧基硅烷、3-(3,4-环氧环己基)乙基甲基二甲氧基硅烷、3-甲基丙烯酰氧基丙基甲基二甲氧基硅烷、3-甲基丙烯酰氧基丙基甲基二乙氧基硅烷、3-巯基丙基甲基二甲氧基硅烷、γ-氨基丙基甲基二乙氧基硅烷、N-(2-氨基乙基)氨基丙基甲基二甲氧基硅烷、3,3,3-三氟丙基甲基二甲氧基硅烷等。
作为三烷氧基硅烷化合物的具体例,可列举出甲基三甲氧基硅烷、甲基三乙氧基硅烷、乙基三甲氧基硅烷、乙基三乙氧基硅烷、丙基三甲氧基硅烷、丙基三乙氧基硅烷、丁基三甲氧基硅烷、丁基三乙氧基硅烷、戊基三甲氧基硅烷、戊基三乙氧基硅烷、庚基三甲氧基硅烷、庚基三乙氧基硅烷、辛基三甲氧基硅烷、辛基三乙氧基硅烷、十二烷基三甲氧基硅烷、十二烷基三乙氧基硅烷、十六烷基三甲氧基硅烷、十六烷基三乙氧基硅烷、十八烷基三甲氧基硅烷、十八烷基三乙氧基硅烷、苯基三甲氧基硅烷、苯基三乙氧基硅烷、乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、γ-氨基丙基三甲氧基硅烷、3-氨基丙基三乙氧基硅烷、γ-缩水甘油氧基丙基三甲氧基硅烷、3-缩水甘油氧基丙基三乙氧基硅烷、γ-甲基丙烯酰氧基丙基三甲氧基硅烷、γ-甲基丙烯酰氧基丙基三乙氧基硅烷、三乙氧基(4-(三氟甲基)苯基)硅烷、十二烷基三乙氧基硅烷、3,3,3-三氟丙基三甲氧基硅烷、(三乙氧基甲硅烷基)环己烷、全氟辛基乙基三乙氧基硅烷、三乙氧基氟硅烷、十三氟-1,1,2,2-四氢辛基三乙氧基硅烷、五氟苯基三甲氧基硅烷、五氟苯基三乙氧基硅烷、3-(七氟异丙氧基)丙基三乙氧基硅烷、十七氟-1,1,2,2-四氢癸基三乙氧基硅烷、三乙氧基-2-噻吩基硅烷、3-(三乙氧基甲硅烷基)呋喃等。
作为四烷氧基硅烷化合物的具体例,可列举出四乙氧基硅烷、四甲氧基硅烷、四丙氧基硅烷等。
这些中,优选3,3,3-三氟丙基甲基二甲氧基硅烷、三乙氧基(4-(三氟甲基)苯基)硅烷、3,3,3-三氟丙基三甲氧基硅烷、全氟辛基乙基三乙氧基硅烷或五氟苯基三甲氧基硅烷、五氟苯基三乙氧基硅烷。
本发明的电荷传输性清漆含有有机硅烷化合物的情况下,就其含量而言,相对于电荷传输性物质和掺杂剂物质的总质量,通常为0.1~50质量%左右,如果考虑抑制得到的薄膜的电荷传输性的降低,并且提高向在上述的阴极侧以与空穴注入层相接的方式层叠的层的空穴注入能力,优选为0.5~40质量%左右,更优选为0.8~30质量%左右,进一步优选为1~20质量%左右。
再有,在本发明的电荷传输性清漆中,除了由上述的苯胺衍生物构成的电荷传输性物质以外,也能够使用公知的其他的电荷传输性物质。
作为制备电荷传输性清漆时使用的有机溶剂,能够使用可良好地溶解电荷传输性物质和掺杂剂物质的高溶解性溶剂。
作为这样的高溶解性溶剂,例如可列举出环己酮、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-咪唑啉酮、二甘醇单甲基醚等有机溶剂,但并不限定于这些。这些溶剂可以1种单独地使用或者将2种以上混合使用,相对于在清漆中使用的全部溶剂,其使用量可以设为5~100质量%。
再有,电荷传输性物质和掺杂剂物质优选均成为了在上述溶剂中完全地溶解或者均匀地分散的状态,更优选完全地溶解。
另外,本发明中,通过使清漆中含有至少1种25℃下具有10~200mPa·s、特别地35~150mPa·s的粘度、常压(大气压)下沸点50~300℃、特别地150~250℃的高粘度有机溶剂,清漆的粘度的调节变得容易,其结果再现性良好地给予平坦性高的薄膜、与采用的涂布方法相符的清漆制备成为可能。
作为高粘度有机溶剂,例如可列举出环己醇、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,但并不限定于这些。这些溶剂可单独地使用,也可将2种以上混合使用。
相对于本发明的清漆中使用的全部溶剂的高粘度有机溶剂的添加比例优选为固体不析出的范围内,只要固体不析出,添加比例优选5~80质量%。
进而,出于对于基板的润湿性的提高、溶剂的表面张力的调节、极性的调节、沸点的调节等目的,相对于清漆中使用的全部溶剂,也可以以1~90质量%、优选地1~50质量%的比例混合其他溶剂。
作为这样的溶剂,例如可列举出丙二醇单甲基醚、乙二醇单丁基醚、二甘醇二乙基醚、二甘醇二甲基醚、二甘醇单乙基醚乙酸酯、二甘醇单丁基醚乙酸酯、二丙二醇单甲基醚、丙二醇单甲基醚乙酸酯、二甘醇单乙基醚、双丙酮醇、γ-丁内酯、乳酸乙酯、乙酸正己酯等,但并不限定于这些。这些溶剂可以1种单独地使用或者将2种以上混合使用。
就本发明的清漆的粘度和表面张力而言,在考虑使用的涂布法的同时根据制作的薄膜的厚度等、固体成分浓度适当地设定,通常在25℃下为1~50mPa·s,其表面张力通常为20~50mN/m。
另外,就本发明中的电荷传输性清漆的固体成分浓度而言,考虑清漆的粘度和表面张力等、制作的薄膜的厚度等适当地设定,通常为0.1~10.0质量%左右,如果考虑提高清漆的涂布性,优选为0.5~5.0质量%左右,更优选为1.0~3.0质量%左右。
作为电荷传输性清漆的制备法,并无特别限定,例如可列举出使本发明的苯胺衍生物溶解于溶剂,向其中加入掺杂剂物质等其他成分的方法;使电荷传输性物质和其他成分的混合物溶解于溶剂中的方法。
另外,有多种有机溶剂的情况下,可在将电荷传输性物质等充分溶解的溶剂中首先使它们溶解,向其中加入其他溶剂,也可在多种有机溶剂的混合溶剂中使电荷传输性物质、其他成分依次溶解或者使它们同时溶解。
本发明中,对于电荷传输性清漆,从再现性良好地得到高平坦性薄膜的观点出发,希望使电荷传输性物质等溶解于有机溶剂后,使用亚微米级的过滤器等进行过滤。
通过将以上说明的电荷传输性清漆在基材上涂布、烧成,从而能够在基材上形成电荷传输性薄膜。
作为清漆的涂布方法,并无特别限定,可列举出浸渍法、旋涂法、转印印刷法、辊涂法、毛刷涂布、喷墨法、喷涂法、狭缝式涂布法等,优选根据涂布方法来调节清漆的粘度和表面张力。
另外,使用本发明的清漆的情况下,对烧成气氛也无特别限定,不仅是大气气氛,即使在氮等非活性气体、真空中也能够得到均匀的成膜面的薄膜,如果考虑再现性良好地得到高电荷传输性的薄膜,则优选大气气氛下。
就烧成温度而言,考虑得到的薄膜的用途、对得到的薄膜赋予的电荷传输性的程度、溶剂的种类、沸点等,在100~260℃左右的范围内适当地设定,使用得到的薄膜作为有机EL元件的空穴注入层的情况下,优选140~250℃左右,更优选145~240℃左右。
再有,烧成时,为了使更高的均匀成膜性显现,在基材上使反应进行,可给予2阶段以上的温度变化,加热例如可使用热板、烘箱等适当的设备进行。
对电荷传输性薄膜的膜厚并无特别限定,在有机EL元件内用作空穴注入层的情况下,优选5~200nm。作为使膜厚变化的方法,有使清漆中的固体成分浓度变化、使涂布时的基板上的溶液量变化等方法。
本发明的电荷传输性薄膜在有机EL元件中能够优选地用作空穴注入层,但也可作为空穴注入传输层等电荷传输性功能层使用。
作为使用本发明的电荷传输性清漆制作OLED元件时的使用材料、制作方法,可列举出下述的使用材料、制作方法,但并不限定于这些。
就使用的电极基板而言,优选预先进行采用洗涤剂、醇、纯水等的液体清洗进行净化,例如,对于阳极基板,优选在使用前即刻进行UV臭氧处理、氧-等离子体处理等表面处理。不过,阳极材料以有机物作为主成分的情况下,也可不进行表面处理。
具有由本发明的电荷传输性清漆得到的薄膜构成的空穴注入层的OLED元件的制作方法的例子如以下所述。
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烧成,在电极上制作空穴注入层。将其导入真空蒸镀装置内,依次蒸镀空穴传输层、发光层、电子传输层、电子传输层/空穴阻挡层、阴极金属,制成OLED元件。再有,根据需要,可在发光层与空穴传输层之间设置电子阻挡层。
作为阳极材料,可列举出以铟锡氧化物(ITO)、铟锌氧化物(IZO)为代表的透明电极、由以铝为代表的金属、它们的合金等构成的金属阳极,优选进行了平坦化处理的阳极材料。也能够使用具有高电荷传输性的聚噻吩衍生物、聚苯胺衍生物。
再有,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、它们的合金等,但并不限定于这些。
作为形成空穴传输层的材料,可列举出(三苯基胺)二聚体衍生物、[(三苯基胺)二聚体]螺二聚体、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-螺双芴、N,N'-双(萘-1-基)-N,N'-双(苯基)-9,9-螺双芴、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-螺双芴、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-螺双芴、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-螺双芴、2,2'-双(N,N-二苯基氨基)-9,9-螺双芴、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-螺双芴、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]三苯基胺(m-MTDATA)、4,4',4″-三[1-萘基(苯基)氨基]三苯基胺(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)等低聚噻吩类等空穴传输性低分子材料等。
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)-4-(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-螺双芴-2-基)-9,9-螺双芴、2,7-双(9,9-螺双芴-2-基)-9,9-螺双芴、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-螺双芴、1,3,5-三(芘-1-基)苯、9,9-双[4-(芘基)苯基]-9H-芴、2,2'-联(9,10-二苯基蒽)、2,7-二芘基-9,9-螺双芴、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]-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)三苯基胺、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-螺双芴、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-螺双芴、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-二乙基氨基-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-螺双芴-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-氮杂二苯并[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,可通过与发光性掺杂剂共蒸镀而形成发光层。
作为发光性掺杂剂,可列举出3-(2-苯并噻唑基)-7-(二乙基氨基)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、喹吖啶酮、N,N'-二甲基-喹吖啶酮、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-羟基苯基)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]均二苯乙烯、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)硼酸酯铱(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-螺双芴、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)二苯基次磷酸酯)铱(III)、双(3-三氟甲基-5-(2-吡啶基)吡唑)(苄基二苯基次磷酸酯)铱(III)、双(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)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-均三甲苯基-N-(6-均三甲苯基喹啉-2(1H)-亚基)喹啉-2-胺-BF2、(E)-2-(2-(4-(二甲基氨基)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-久洛尼定基-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尼定基-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尼定-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-酮)铱(III)、双(2-苯基喹啉)(2,2,6,6-四甲基庚烷-3,5-二酮)铱(III)、双(苯基异喹啉)(2,2,6,6-四甲基庚烷-3,5-二酮)铱(III)、双(4-苯基噻吩并[3,2-c]吡啶合-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)、八乙基卟吩铂(II)、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)喹喔啉]铱(III)等。
作为形成电子传输层的材料,可列举出8-羟基喹啉酚-锂、2,2',2″-(1,3,5-苯三基)-三(1-苯基-1-H-苯并咪唑)、2-(4-联苯)5-(4-叔-丁基苯基)-1,3,4-噁二唑、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-噁二唑-5-基]苯、6,6'-双[5-(联苯-4-基)-1,3,4-噁二唑-2-基]-2,2'-联吡啶、3-(4-联苯)-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-噁二唑-5-基]-9,9-二甲基芴、1,3-双[2-(4-叔-丁基苯基)-1,3,4-噁二唑-5-基]苯、三(2,4,6-三甲基-3-(吡啶-3-基)苯基)硼烷、1-甲基-2-(4-(萘-2-基)苯基)-1H-咪唑并[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)-苯-3-基]联苯、1,3,5-三[(3-吡啶基)-苯-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)、醋酸锂、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。
另外,具有由本发明的电荷传输性清漆得到的薄膜构成的空穴注入层的有机EL元件的制作方法的其他的例子如以下所述。
在上述EL元件制作中,通过代替进行空穴传输层、发光层、电子传输层、电子注入层的真空蒸镀操作而依次形成空穴传输层(以下记为空穴传输性高分子层)、发光层(以下记为发光性高分子层),能够制作具有由本发明的电荷传输性清漆形成的电荷传输性薄膜的有机EL元件。
具体地,在阳极基板上涂布本发明的电荷传输性清漆,采用上述的方法制作空穴注入层,在其上依次形成空穴传输性高分子层、发光性高分子层,进而蒸镀阴极电极,制成有机EL元件。
作为使用的阴极和阳极材料,能够使用与上述的阴极和阳极材料同样的阴极和阳极材料,能够进行同样的清洗处理、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,可列举出下述方法:通过在空穴传输性高分子材料或发光性高分子材料、或者在它们中加入了掺杂剂物质的材料中加入溶剂而溶解,或者均匀地分散,在空穴注入层或空穴传输性高分子层上涂布后,分别进行烧成,从而成膜。
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)-共-(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)-共-(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)-共-(N,N'-双{对-丁基苯基}-1,4-二氨基亚苯基)]、用聚硅倍半氧烷封端的聚[N,N'-双(4-丁基苯基)-N,N'-双(苯基)-联苯胺]、聚[(9,9-二辛基芴基-2,7-二基)-共-(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-亚苯基亚乙烯基)(MEH-PPV)等聚亚苯基亚乙烯基衍生物、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,作为溶解或均匀分散法,可列举出搅拌、加热搅拌、超声波分散等方法。
作为涂布方法,并无特别限定,可列举出喷墨法、喷涂法、浸渍法、旋涂法、转印印刷法、辊涂法、毛刷涂布等。再有,涂布优选在氮、氩等非活性气体下进行。
作为烧成的方法,可列举出在非活性气体下或真空中、用烘箱或热板进行加热的方法。
再有,在电极和上述各层之间的任意之间,根据需要可设置空穴阻挡层、电子阻挡层等。例如,作为形成电子阻挡层的材料,可列举出三(苯基吡唑)铱等。
构成阳极和阴极以及在它们之间所形成的层的材料,由于因制造具有底部发射结构、顶部发射结构的哪一种结构的元件而异,因此考虑这点来适当地选择材料。
通常,在底部发射结构的元件中,在基板侧使用透明阳极,从基板侧将光取出,而在顶部发射结构的元件中,使用由金属构成的反射阳极,从位于基板的相反方向的透明电极(阴极)侧将光取出,因此,例如对于阳极材料而言,制造底部发射结构的元件时使用ITO等的透明阳极,制造顶部发射结构的元件时使用Al/Nd等的反射阳极。
就本发明的有机EL元件而言,为了防止特性恶化,可按照常规方法、根据需要与捕水剂等一起进行密封。
实施例
以下列举制造例和实施例对本发明更具体地说明,但本发明并不限定于下述的实施例。应予说明,使用的装置如以下所述。
(1)MALDI-TOF-MS:Bruker Daltonics公司制造、autoflex III smartbeam
(2)1H-NMR:日本电子(株)制造JNM-ECP300 FT NMR SYSTEM
(3)基板清洗:长州产业(株)制造基板清洗装置(减压等离子体方式)
(4)清漆的涂布:ミカサ(株)制造旋涂器MS-A100
(5)膜厚测定:(株)小坂研究所制造微细形状测定机SURFCORDERET-4000
(6)EL元件的制作:长州产业(株)制造多功能蒸镀装置系统C-E2L1G1-N
(7)EL元件的亮度等的测定:(有)テック·ワールド制造I-V-L测定系统
(8)EL元件的寿命测定(半衰期的测定):(株)イーエッチシー制造有机EL亮度寿命评价系统PEL-105S
[1]化合物的合成
[制造例1]N1-(菲-9-基)-N4-(4-(菲-9-基氨基)苯基)苯-1,4-二胺的合成
[化36]
将N1-(4-氨基苯基)苯-1,4-二胺2.01g、9-溴菲5.68g、Pd(PPh3)40.46g和叔丁氧基钠2.32g装入反应容器中,进行了氮置换后,装入二甲苯50mL,在加热回流条件下搅拌5小时使其反应。将反应液冷却到室温后,加入甲苯和饱和食盐水,将生成的不溶物过滤。将得到的滤物按离子交换水、甲醇、甲苯的顺序洗净,使洗净后的滤物溶解于四氢呋喃(THF),在该溶液中加入活性炭,在50℃下搅拌了1小时。通过过滤将活性炭除去后,将得到的滤液浓缩、干燥,得到了目标的N1-(菲-9-基)-N4-(4-(菲-9-基氨基)苯基)苯-1,4-二胺(苯胺衍生物1)(产量:3.48g,收率:63%)。
1H-NMR(300MHz,DMSO-d6)δ[ppm]:8.83(d,J=8.9Hz,2H),8.67(d,J=8.9Hz,2H),8.41(d,J=7.7Hz,2H),7.97(s,2H),7.87(s,1H),7.65-7.76(m,6H),7.39-7.50(m,4H),7.24(s,2H),7.17(d,J=8.9Hz,4H),7.10(d,J=8.9Hz,4H).
[制造例2]N1-(9,9’-螺双[芴]-2-基)-N4-(4-(9,9’-螺双[芴]-2-基氨基)苯基)苯-1,4-二胺的合成
[化37]
在烧杯内装入双(4-氨基苯基)胺0.500g、2-溴-9,9’-螺双[芴]2.18g、Pd(PPh3)40.117g和叔丁氧基钠0.579g后,对烧杯内进行了氮置换。向其中装入二甲苯20mL,在加热回流条件下搅拌了5小时。
然后,将反应混合物冷却到室温,将冷却的反应混合物、甲苯和离子交换水混合,进行分液处理,将得到的有机层用离子交换水洗净,进而用饱和食盐水洗净。
接下来,将洗净后的有机层用硫酸钠干燥后浓缩,使用浓缩液进行硅胶柱色谱(展开溶剂:甲苯),通过采用色谱(TLC)法确认目标物的有无,从而将包含目标物的级分分取。
最后,在减压下从分取的级分中将溶剂除去,得到了目标的N1-(9,9’-螺双[芴]-2-基)-N4-(4-(9,9’-螺双[芴]-2-基氨基)苯基)苯-1,4-二胺(苯胺衍生物2)(产量:0.926g,收率:46%)。
MALDI-TOF-MS m/Z测定值:826.45([M]+计算值:827.33).
[制造例3]N1-(萘-1-基)-N4-(4-((4-(萘-1-基(苯基)氨基)苯基氨基)苯基氨基)苯基)-N1-苯基苯-1,4-二胺的合成
[化38]
在烧杯内装入双(4-氨基苯基)胺1.59g、N-(4-溴苯基)-N-苯基萘-1-胺6.29g、Pd(PPh3)40.373g和叔丁氧基钠1.84g后,对烧杯内进行了氮置换。向其中放入二甲苯100mL,在加热回流条件下搅拌了4.5小时。
搅拌结束后,将反应混合物冷却到室温,将冷却的反应混合物和醋酸乙酯和离子交换水混合,进行了分液处理。将得到的有机层以离子交换水、饱和食盐水的顺序洗净,用硫酸镁进行了干燥。将其过滤,将溶剂减压馏除后,采用硅胶柱色谱(展开溶剂:氯仿/醋酸乙酯=100/0→0/100)进行分离、精制,收集包含目标物的级分,将溶剂减压馏除后,用1,4-二噁烷/乙醇进行重结晶。最后将结晶过滤,将得到的滤物干燥,得到了N1-(萘-1-基)-N4-(4-((4-(萘-1-基(苯基)氨基)苯基氨基)苯基氨基)苯基)-N1-苯基苯-1,4-二胺(苯胺衍生物3)(产量:0.994g、收率:16%)。
1H-NMR(400MHz,THF-d8)δ[ppm]:7.97(d,J=8.4Hz,2H),7.85(d,J=8.0Hz,2H),7.71(d,J=8.0Hz,2H),7.38-7.44(m,4H),7.25-7.33(m,4H),6.73-7.07(m,29H).
MALDI-TOF-MS m/Z测定值:785.00([M]+计算值:785.35).
[制造例4]N1-(9-苯基-9H-咔唑-3-基)-N4-(4-((9-苯基-9H-咔唑-3-基)氨基)苯基)苯-1,4-二胺的合成
[化39]
在烧杯内装入双(4-氨基苯基)胺3.18g、3-溴-9-苯基-9H-咔唑11.3g、Pd(dba)20.183g和叔丁氧基钠3.39g后,对烧杯内进行了氮置换。接下来,加入甲苯200mL、预先制备的二-叔-丁基(苯基)膦的甲苯溶液1.45mL(浓度:98g/L),在50℃下搅拌。2小时后升温到80℃,进一步搅拌了3小时。搅拌结束后,将反应混合物冷却到室温,过滤。将滤液的溶剂减压馏除后,采用硅胶柱色谱(展开溶剂:甲苯/醋酸乙酯=100/0→70/30)进行分离、精制,收集包含目标物的级分,将溶剂减压馏除。使其溶解于THF中,滴入搅拌着的甲醇中,将得到的浆料进一步在室温下搅拌。最后,将浆料过滤,将得到的滤物干燥,得到了N1-(9-苯基-9H-咔唑-3-基)-N4-(4-((9-苯基-9H-咔唑-3-基)氨基)苯基)苯-1,4-二胺(苯胺衍生物4)(产量:5.14g,收率:47%)。
1H-NMR(400MHz,DMSO-d6)δ[ppm]:8.12-8.14(m,2H),7.81(d,J=1.6Hz,2H),7.49-7.74(m,13H),7.37-7.39(m,4H),7.30(d,J=8.8Hz,2H),7.19-7.23(m,2H),7.14(dd,J=8.8,2.0Hz,2H),6.96-7.04(m,8H).
MALDI-TOF-MS m/Z测定值:681.04([M]+计算值:681.29).
[2]电荷传输性清漆的制备
[实施例1-1]
使0.105g作为电荷传输性物质的苯胺衍生物1和0.139g作为掺杂剂物质的采用国际公开第2006/025342号记载的方法合成的由上述式(4-1)表示的芳基磺酸化合物溶解于1,3-二甲基-2-咪唑啉酮(以下记为DMI)4.0g中。向其中加入环己醇6.0g和丙二醇2.0g,搅拌,制备了电荷传输性清漆。
[实施例1-2]
使0.088g作为电荷传输性物质的苯胺衍生物1和0.116g由上述式(4-1)表示的芳基磺酸化合物溶解于3.3g DMI。向其中加入2,3-丁二醇(以下记为2,3-BD)4.0g和二丙二醇单甲基醚(以下记为DPM)2.7g,搅拌,制备了电荷传输性清漆。
[实施例1-3]
除了将苯胺衍生物1和由式(4-1)表示的芳基磺酸化合物的使用量分别变为0.068g和0.136g以外,与实施例1-2同样地制备了电荷传输性清漆。
[实施例1-4]
除了将苯胺衍生物1和由式(4-1)表示的芳基磺酸化合物的使用量分别变为0.058g和0.148g以外,与实施例1-2同样地制备了电荷传输性清漆。
[实施例1-5]
除了使用了0.135g苯胺衍生物2和0.110g由式(4-1)表示的芳基磺酸化合物以外,与实施例1-1同样地制备了电荷传输性清漆。
[实施例1-6]
除了使用了0.112g苯胺衍生物2和0.092g由式(4-1)表示的芳基磺酸化合物以外,与实施例1-2同样地制备了电荷传输性清漆。
[实施例1-7]
除了使用了0.092g苯胺衍生物2和0.112g由式(4-1)表示的芳基磺酸化合物以外,与实施例1-2同样地制备了电荷传输性清漆。
[实施例1-8]
除了使用了0.075g苯胺衍生物3和0.129g由式(4-1)表示的芳基磺酸化合物以外,与实施例1-2同样地制备了电荷传输性清漆。
[实施例1-9]
除了使用了0.065g苯胺衍生物3和0.139g由式(4-1)表示的芳基磺酸化合物以外,与实施例1-2同样地制备了电荷传输性清漆。
[实施例1-10]
除了使用了0.057g苯胺衍生物3和0.147g由式(4-1)表示的芳基磺酸化合物以外,与实施例1-2同样地制备了电荷传输性清漆。
[实施例1-11]
使0.137g苯胺衍生物4和0.271g由式(4-1)表示的芳基磺酸化合物溶解于6.6gDMI。向其中加入8.0g 2,3-BD和5.4g DPM,搅拌,制备了电荷传输性清漆。
[实施例1-12]
除了使用了0.117g苯胺衍生物4和0.291g由式(4-1)表示的芳基磺酸化合物以外,与实施例1-11同样地制备了电荷传输性清漆。
[实施例1-13]
除了使用了0.103g苯胺衍生物4和0.306g由式(4-1)表示的芳基磺酸化合物以外,与实施例1-11同样地制备了电荷传输性清漆。
[3]有机EL元件的制造和特性评价
[实施例2-1]
使用旋涂器将实施例1-1中得到的清漆涂布于ITO基板后,在80℃下干燥1分钟,进而,在大气气氛下、230℃下烧成15分钟,在ITO基板上形成了30nm的均一的薄膜。作为ITO基板,使用在表面上以膜厚150nm将铟锡氧化物(ITO)图案化的25mm×25mm×0.7t的玻璃基板,在使用前采用O2等离子体清洗装置(150W、30秒)将表面上的杂质除去。
接下来,对于形成了薄膜的ITO基板,使用蒸镀装置(真空度1.0×10-5Pa)依次层叠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)、氟化锂和铝的薄膜,得到了有机EL元件。此时,就蒸镀速率而言,对于α-NPD、Alq3和铝在0.2nm/秒、对于氟化锂在0.02nm/秒的条件下分别进行,使膜厚分别为30nm、40nm、0.5nm和100nm。
再有,为了防止空气中的氧、水等的影响导致的特性劣化,将有机EL元件用封装基板封装后,对其特性进行了评价(下同)。按照以下的程序进行了封装。在氧浓度2ppm以下、露点-85℃以下的氮气氛中将有机EL元件收入封装基板之间,采用粘接材料((株)MORESCO制造、MORESCO MOISTURE CUT WB90US(P))将封装基板贴合。此时,将捕水剂(ダイニック(株)制造、HD-071010W-40)与有机EL元件一起收入封装基板内。对于贴合的封装基板,照射了UV光(波长:365nm、照射量:6,000mJ/cm2)后,在80℃下进行退火处理1小时,使粘接材料固化。
[实施例2-2~2-7]
除了代替实施例1-1中得到的清漆而分别使用了实施例1-2~1-12、1-14、1-16、1-18、1-20~1-24中得到的清漆以外,采用与实施例2-1同样的方法制作了有机EL元件。
[实施例2-8]
使用旋涂器将实施例1-8中得到的清漆涂布于ITO基板后,在80℃下干燥1分钟,进而,在大气气氛下、230℃下烧成15分钟,在ITO基板上形成了30nm的均匀的薄膜。作为ITO基板,使用在表面上以膜厚150nm将铟锡氧化物(ITO)图案化的25mm×25mm×0.7t的玻璃基板,在使用前采用O2等离子体清洗装置(150W、30秒)将表面上的杂质除去。
接下来,对于形成了薄膜的ITO基板,使用蒸镀装置(真空度1.0×10-5Pa)以0.2nm/秒将α-NPD成膜30nm。接下来,将CBP和Ir(PPy)3共蒸镀。就共蒸镀而言,控制蒸镀速率以致Ir(PPy)3的浓度成为6%,层叠了40nm。接下来,依次层叠氟化锂和铝的薄膜,得到了有机EL元件。此时,就蒸镀速率而言,对于铝在0.2nm/秒、对于氟化锂在0.02nm/秒的条件下分别进行,使膜厚分别为0.5nm和100nm。
[实施例2-9~2-13]
除了代替实施例1-8中得到的清漆而分别使用了实施例1-9~1-13中得到的清漆以外,采用与实施例2-8同样的方法制作了有机EL元件。
对于实施例2-1~2-7中制作的元件测定了以亮度1000cd/m2驱动时的驱动电压、电流密度和发光效率,对于实施例2-8~2-13中制作的元件测定了以亮度5000cd/m2驱动时的驱动电压、电流密度和发光效率,以及测定了实施例2-1、2-2、2-5、2-6、2-8和2-9中制作的元件的亮度的半衰期(初期5000cd/m2)。将结果示于表6中。
[表6]
如表6中所示那样,可知具有由本发明的电荷传输性清漆得到的电荷传输性薄膜作为空穴注入层的有机EL元件的耐久性优异。
Claims (9)
2.电荷传输性物质,其由权利要求1所述的苯胺衍生物构成。
3.电荷传输性材料,其包含权利要求2所述的电荷传输性物质。
4.电荷传输性清漆,其包含权利要求2所述的电荷传输性物质和有机溶剂。
5.权利要求4所述的电荷传输性清漆,其还包含掺杂剂物质。
6.权利要求5所述的电荷传输性清漆,其中,上述掺杂剂物质为芳基磺酸化合物。
7.使用权利要求4~6的任一项所述的电荷传输性清漆制作的电荷传输性薄膜。
8.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。
9.电荷传输性薄膜的制造方法,其特征在于,在基材上涂布权利要求4~6的任一项所述的电荷传输性清漆,使溶剂蒸发。
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Application Number | Priority Date | Filing Date | Title |
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JP2015033810 | 2015-02-24 | ||
JP2015-033810 | 2015-02-24 | ||
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KR102128152B1 (ko) * | 2017-07-07 | 2020-06-29 | 주식회사 엘지화학 | 화합물, 이를 포함하는 코팅 조성물, 이를 이용한 유기 발광 소자 및 이의 제조방법 |
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WO2016136544A1 (ja) | 2016-09-01 |
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KR20170119697A (ko) | 2017-10-27 |
TWI673255B (zh) | 2019-10-01 |
JP2019206591A (ja) | 2019-12-05 |
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