CN106103406B - 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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- CN106103406B CN106103406B CN201580013956.8A CN201580013956A CN106103406B CN 106103406 B CN106103406 B CN 106103406B CN 201580013956 A CN201580013956 A CN 201580013956A CN 106103406 B CN106103406 B CN 106103406B
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- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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- ZKYQRJXGGLVQML-UHFFFAOYSA-N iridium(3+);2-phenylpyridine Chemical compound [Ir+3].C1=CC=CC=C1C1=CC=CC=N1 ZKYQRJXGGLVQML-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
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- UXTZGRFXOOOBPM-UHFFFAOYSA-N iridium;5-phenyl-1h-pyrazole Chemical compound [Ir].N1C=CC(C=2C=CC=CC=2)=N1 UXTZGRFXOOOBPM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
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- WPJCJMUJHATBCW-UHFFFAOYSA-N n,n-bis(4-methylphenyl)anthracen-1-amine Chemical compound C1=CC(C)=CC=C1N(C=1C2=CC3=CC=CC=C3C=C2C=CC=1)C1=CC=C(C)C=C1 WPJCJMUJHATBCW-UHFFFAOYSA-N 0.000 description 1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
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- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HCIIFBHDBOCSAF-UHFFFAOYSA-N octaethylporphyrin Chemical class N1C(C=C2C(=C(CC)C(C=C3C(=C(CC)C(=C4)N3)CC)=N2)CC)=C(CC)C(CC)=C1C=C1C(CC)=C(CC)C4=N1 HCIIFBHDBOCSAF-UHFFFAOYSA-N 0.000 description 1
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- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 1
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- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
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- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
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- 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
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- VQMWBBYLQSCNPO-UHFFFAOYSA-N promethium atom Chemical compound [Pm] VQMWBBYLQSCNPO-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 150000003220 pyrenes Chemical class 0.000 description 1
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- 150000003248 quinolines Chemical class 0.000 description 1
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- 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
- 238000007761 roller coating Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
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- CGFYHILWFSGVJS-UHFFFAOYSA-N silicic acid;trioxotungsten Chemical compound O[Si](O)(O)O.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 CGFYHILWFSGVJS-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
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- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- IRFHMTUHTBSEBK-QGZVFWFLSA-N tert-butyl n-[(2s)-2-(2,5-difluorophenyl)-3-quinolin-3-ylpropyl]carbamate Chemical compound C1([C@H](CC=2C=C3C=CC=CC3=NC=2)CNC(=O)OC(C)(C)C)=CC(F)=CC=C1F IRFHMTUHTBSEBK-QGZVFWFLSA-N 0.000 description 1
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 1
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical class CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 description 1
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- 150000003577 thiophenes Chemical class 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- XVYIJOWQJOQFBG-UHFFFAOYSA-N triethoxy(fluoro)silane Chemical compound CCO[Si](F)(OCC)OCC XVYIJOWQJOQFBG-UHFFFAOYSA-N 0.000 description 1
- FCIABWJRBPKYJO-UHFFFAOYSA-N triethoxy(furan-3-yl)silane Chemical compound CCO[Si](OCC)(OCC)C=1C=COC=1 FCIABWJRBPKYJO-UHFFFAOYSA-N 0.000 description 1
- SAWDTKLQESXBDN-UHFFFAOYSA-N triethoxy(heptyl)silane Chemical compound CCCCCCC[Si](OCC)(OCC)OCC SAWDTKLQESXBDN-UHFFFAOYSA-N 0.000 description 1
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 description 1
- FHVAUDREWWXPRW-UHFFFAOYSA-N triethoxy(pentyl)silane Chemical compound CCCCC[Si](OCC)(OCC)OCC FHVAUDREWWXPRW-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- HILHCDFHSDUYNX-UHFFFAOYSA-N trimethoxy(pentyl)silane Chemical compound CCCCC[Si](OC)(OC)OC HILHCDFHSDUYNX-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
- 125000006617 triphenylamine group Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
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Abstract
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,而且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亮度特性的有机EL元件。
Description
技术领域
本发明涉及苯胺衍生物及其利用。
发明内容
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,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,本发明人开发出了可适用于各种湿法、且给予在应用于有机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,目的在于提供显示对有机溶剂的良好的溶解性、且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亮度特性的有机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,反复深入研究,结果发现:不可能采取醌二亚胺结构的规定的苯胺衍生物具有对有机溶剂的优异的溶解性,由使其溶解于有机溶剂而制备的清漆得到发挥高电荷传输性的薄膜,以及将该薄膜应用于有机EL元件的空穴注入层的情况下,得到高亮度的元件,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,R1~R5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,Ph1相互独立地表示由式(P1)表示的基团,
[化2]
(式中,R6~R9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)~(A14)表示的任一个基团,
[化3]
m表示1~5的整数。]
2.1的苯胺衍生物,其中,上述R1~R9全部为氢原子,
3.1或2的苯胺衍生物,其中,上述Ar1相互独立地为由式(A1)~(A12)表示的任一个基团,
4.3的苯胺衍生物,其中,上述Ar1相互独立地为由式(A1)~(A3)、(A5)~(A7)、和(A10)~(A12)表示的任一个基团,
5.1~4的任一项的苯胺衍生物,其中,上述Ar1全部为相同的基团,
6.电荷传输性物质,其由1~5的任一项的苯胺衍生物构成,
7.电荷传输性材料,其包含6的电荷传输性物质,
8.电荷传输性清漆,其包含6的电荷传输性物质、和有机溶剂,
9.8的电荷传输性清漆,其还包含掺杂剂物质,
10.9的电荷传输性清漆,其中,上述掺杂剂物质包含卤代四氰基醌二甲烷化合物,
11.10的电荷传输性清漆,其中,上述掺杂剂物质还包含杂多酸,
12.使用8~11的任一项的电荷传输性清漆制作的电荷传输性薄膜,
13.电子设备,其具有12的电荷传输性薄膜,
14.有机电致发光元件,其具有12的电荷传输性薄膜,
15.电荷传输性薄膜的制造方法,其特征在于,在基材上涂布8~11的任一项的电荷传输性清漆,使溶剂蒸发,
16.1的苯胺衍生物的制造方法,其特征在于,在催化剂存在下使由式(2)
[化4]
(式中,R1~R5、Ph1、和m表示与上述相同的含义。)
表示的胺化合物与由式(3)
[化5]
Ar1-Z (3)
(式中,Z表示卤素原子或拟卤素基,Ar1表示与上述相同的含义。)
表示的芳基化合物反应。
发明的效果
本发明的苯胺衍生物易溶解于有机溶剂中,使其与掺杂剂一起溶解于有机溶剂中,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,因此能够适宜用作以有机EL元件为首的电子设备用薄膜。特别地,通过将该薄膜应用于有机EL元件的空穴注入层,能够得到亮度特性优异的有机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
以下对本发明更详细地说明。
本发明涉及的苯胺衍生物由式(1)表示。
[化6]
式中,Ph1相互独立地表示由式(P1)表示的基团。
[化7]
上述R1~R9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,可以是直链状、分支链状、环状的任一种,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。
这些中,R1~R9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。
上述式(1)中的Ar1相互独立地表示由式(A1)~(A14)表示的任一个基团。
这些中,从提高化合物对于有机溶剂的溶解性、得到的薄膜的电荷传输性的方面出发,优选由式(A1)~(A12)表示的任一个基团,更优选由式(A1)~(A3)、(A5)~(A7)、和(A10)~(A12)表示的任一个基团,进一步优选由式(A1)、(A5)、和(A10)~(A12)表示的任一个基团,更进一步优选由式(A1)和(A5)表示的任一个基团。
[化8]
上述式(1)中的m表示1~5的整数,从提高化合物对有机溶剂的溶解性的观点出发,优选4以下,更优选3以下,从提高电荷传输性的观点出发,优选2以上,更优选3以上。
再有,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,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。
上述式(1)中,Ar1优选全部为相同的基团,Ph1优选全部为相同的基团。
本发明的由式(1)表示的苯胺衍生物能够在催化剂存在下使由式(2)表示的胺化合物与由式(3)表示的芳基化合物反应而制造。
[化9]
(式中,Z表示卤素原子或拟卤素基,R1~R5、Ar1、Ph1、和m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。
作为拟卤素基,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。
就由式(2)表示的胺化合物与由式(3)表示的芳基化合物的进料比而言,相对于胺化合物的全部NH基的物质量,可以使芳基化合物成为当量以上,优选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)二氯化钯)、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)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,这些催化剂可以与公知的适当的配体一起使用。
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,可以使其为0.2mol左右,优选0.15mol左右。
另外,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,可以使其为0.1~5当量,优选1~2当量。
上述各反应可在溶剂中进行。使用溶剂的情况下,就其种类而言,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(二乙基醚、二异丙基醚、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、甲基乙基酮、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。
就反应温度而言,可在使用的溶剂的熔点至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,可以按照常规方法进行后处理,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。
[化10]
本发明的电荷传输性清漆包含:由式(1)所示的苯胺衍生物构成的电荷传输性物质、和有机溶剂,但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,只要在清漆中使用的至少1种的溶剂中溶解,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。
特别地,作为无机系的掺杂剂物质,优选杂多酸。
杂多酸为具有代表性地由式(D1)表示的Keggin型或由式(D2)表示的Dawson型的化学结构表示的、杂原子位于分子的中心的结构,作为钒(V)、钼(Mo)、钨(W)等的含氧酸的同多酸与异种元素的含氧酸缩合而成的多酸。作为这样的异种元素的含氧酸,主要可列举出硅(Si)、磷(P)、砷(As)的含氧酸。
[化11]
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,这些可以单独使用,也可以将2种以上组合使用。应予说明,本发明中使用的杂多酸可作为市售品获得,另外,也可以采用公知的方法合成。
特别地,使用1种杂多酸的情况下,这1种杂多酸优选磷钨酸或磷钼酸,最优选磷钨酸。另外,使用2种以上的杂多酸的情况下,这2种以上的杂多酸中的1个优选磷钨酸或磷钼酸,更优选磷钨酸。
应予说明,杂多酸在元素分析等的定量分析中,即使相对于由通式表示的结构,元素的数多或少,只要其是作为市售品获得的产品或者按照公知的合成方法适当地合成的产物,都能够在本发明中使用。
即,例如,一般地,磷钨酸用化学式H3(PW12O40)·nH2O表示,磷钼酸用化学式H3(PMo12O40)·nH2O表示,在定量分析中,即使该式中的P(磷)、O(氧)或W(钨)或Mo(钼)的数多或者少,只要其为作为市售品获得的产品或者按照公知的合成方法适当地合成的产物,则都能够在本发明中使用。这种情况下,本发明中规定的杂多酸的质量,不是合成物、市售品中的纯粹的磷钨酸的质量(磷钨酸含量),而是意味着作为市售品可获得的形态和采用公知的合成法可分离的形态下包含水合水、其他杂质等的状态下的总质量。
本发明的电荷传输性清漆中所含的杂多酸,以质量比计,相对于由本发明的苯胺衍生物构成的电荷传输性物质1,可以使其为0.01~50左右,优选为0.1~10左右,更优选为1.0~5.0左右。
另一方面,作为有机系的掺杂剂物质,特别优选四氰基醌二甲烷衍生物、苯醌衍生物。
作为四氰基醌二甲烷衍生物的具体例,可列举出7,7,8,8-四氰基醌二甲烷(TCNQ)、由式(4)表示的卤代四氰基醌二甲烷等。
另外,作为苯醌衍生物的具体例,可列举出四氟-1,4-苯醌(F4BQ)、 四氯-1,4-苯醌(四氯代对苯醌)、四溴-1,4-苯醌、2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ)等。
[化12]
式中,R10~R13相互独立地表示氢原子或卤素原子,但至少1个为卤素原子,优选至少2个为卤素原子,更优选至少3个为卤素原子,最优选全部为卤素原子。
作为卤素原子,可列举出与上述相同的卤素原子,优选氟原子或氯原子,更优选氟原子。
作为卤代四氰基醌二甲烷化合物的具体例,可列举出2-氟-7,7,8,8-四氰基醌二甲烷、2-氯-7,7,8,8-四氰基醌二甲烷、2,5-二氟-7,7,8,8-四氰基醌二甲烷、2,5-二氯-7,7,8,8-四氰基醌二甲烷、2,3,5,6-四氯-7,7,8,8-四氰基醌二甲烷、2,3,5,6-四氟-7,7,8,8-四氰基醌二甲烷(F4TCNQ)等,本发明中,最优选F4TCNQ。
就本发明的电荷传输性清漆中的四氰基醌二甲烷衍生物和苯醌衍生物的含量而言,相对于本发明的苯胺衍生物,优选为0.0001~50当量,更优选为0.001~20当量,进一步优选为0.01~10当量。
本发明中,如果考虑再现性良好地得到高电荷传输性的薄膜、掺杂剂物质的获得容易性等,作为掺杂剂物质,优选包含卤代四氰基醌二甲烷和苯醌衍生物的至少1种,更优选包含F4TCNQ和DDQ的至少1种。
另外,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、掺杂剂物质的获得容易性等,作为掺杂剂物质,优选包含卤代四氰基醌二甲烷和苯醌衍生物中的至 少1种和杂多酸,更优选包含卤代四氰基醌二甲烷和苯醌衍生物中的至少1种以及磷钨酸和磷钼酸中的至少1种,进一步优选包含F4TCNQ和DDQ中的至少1种以及磷钨酸。
进而,使用得到的薄膜作为有机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,则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。
作为这些烷氧基硅烷化合物,例如可列举出由式(5)~(7)表示的化合物。
Si(OR)4 (5)
SiR′(OR)3 (6)
Si(R′)2(OR)2 (7)
式中,R相互独立地表示可被Z1取代的碳数1~20的烷基、可被Z1取代的碳数2~20的烯基、可被Z1取代的碳数2~20的炔基、可被Z2取代的碳数6~20的芳基、或可被Z2取代的碳数2~20的杂芳基,R′相互独立地表示可被Z3取代的碳数1~20的烷基、可被Z3取代的碳数2~20的烯基、可被Z3取代的碳数2~20的炔基、可被Z4取代的碳数6~20的芳基、或可被Z4取代的碳数2~20的杂芳基。
Z1表示卤素原子、可被Z5取代的碳数6~20的芳基、或可被Z5取代的碳数2~20的杂芳基,Z2表示卤素原子、可被Z5取代的碳数1~20的烷基、可被Z5取代的碳数2~20的烯基、或可被Z5取代的碳数2~20的炔基。
Z3表示卤素原子、可被Z5取代的碳数6~20的芳基、可被Z5取代的碳数2~20的杂芳基、环氧环己基、缩水甘油氧基、甲基丙烯酰氧基、丙烯酰氧基、脲基(-NHCONH2)、硫醇基、异氰酸酯基(-NCO)、氨基、-NHY1基、或-NY2Y3基,Z4表示卤素原子、可被Z5取代的碳数1~20的烷基、可被Z5取代的碳数2~20的烯基、可被Z5取代的碳数2~20的炔基、环氧环己基、缩水甘油氧基、甲基丙烯酰氧基、丙烯酰氧基、脲基(-NHCONH2)、硫醇基、异氰酸酯基(-NCO)、氨基、-NHY1基、或-NY2Y3基,Y1~Y3相互独立地表示可被Z5取代的碳数1~20的烷基、可被Z5取代的碳数2~20的烯基、可被Z5取代的碳数2~20的炔基、可被Z5取代的碳数6~20的芳基、或可被Z5取代的碳数2~20的杂芳基。
Z5表示卤素原子、氨基、硝基、氰基或硫醇基。
作为式(5)~(7)中的、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,可列举出与上述同样的基团。
R和R′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。
作为R,优选可被Z1取代的、碳数1~20的烷基或碳数2~20的烯基、或者可被Z2取代的碳数6~20的芳基,更优选可被Z1取代的、碳数1~6的烷基或碳数2~6的烯基、或者可被Z2取代的苯基,进一步优选可被Z1取代的碳数1~4的烷基或可被Z2取代的苯基,进一步优选可被Z1取代的、甲基或乙基。
另外,作为R′,优选可被Z3取代的碳数1~20的烷基或可被Z4取代的碳数6~20的芳基,更优选可被Z3取代的碳数1~10的烷基或可被Z4取代的碳数6~14的芳基,进一步优选可被Z3取代的碳数1~6的烷基、或可被Z4取代的碳数6~10的芳基,进一步优选可被Z3取代的碳数1~4的烷基或可被Z4取代的苯基。
应予说明,多个R可全部相同也可不同,多个R′也可全部相同也可不同。
作为Z1,优选卤素原子或者可被Z5取代的碳数6~20的芳基,更 优选氟原子或者可被Z5取代的苯基,最优选不存在(即,为未取代)。
另外,作为Z2,优选卤素原子或者可被Z5取代的碳数1~20的烷基,更优选氟原子或者可被Z5取代的碳数1~10的烷基,最优选不存在(即,为未取代)。
另一方面,作为Z3,优选卤素原子、可被Z5取代的苯基、可被Z5取代的呋喃基、环氧环己基、缩水甘油氧基、甲基丙烯酰氧基、丙烯酰氧基、脲基、硫醇基、异氰酸酯基、氨基、可被Z5取代的苯基氨基、或者可被Z5取代的二苯基氨基,更优选卤素原子,进一步优选氟原子、或不存在(即,为未取代)。
另外,作为Z4,优选卤素原子、可被Z5取代的碳数1~20的烷基、可被Z5取代的呋喃基、环氧环己基、缩水甘油氧基、甲基丙烯酰氧基、丙烯酰氧基、脲基、硫醇基、异氰酸酯基、氨基、可被Z5取代的苯基氨基、或可被Z5取代的二苯基氨基,更优选卤素原子,进一步优选氟原子、或不存在(即,为未取代)。
而且,作为Z5,优选卤素原子,更优选氟原子或不存在(即,为未取代)。
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、3-氨基丙基三甲氧基硅烷、3-氨基丙基三乙氧基硅烷、3-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、3-甲基丙烯酰氧基丙基三甲氧基硅烷、3-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、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,其含量相对于电荷传输性物质(包含掺杂剂物质的情况下为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下降、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中的空穴注入能力,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。
应予说明,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,N-二甲基异丁酰胺、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1种单独地使用或者将2种以上混合使用,其使用量相对于清漆中使用的全部溶剂,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、适于采用的涂布方法的清漆的制备成为可能。
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。这些溶剂可以单独地使用,也可以将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,为了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,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。
本发明的清漆的粘度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。
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方法,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高溶解性溶剂,向其中加入高粘度有机溶剂的方法;将高溶解性溶剂和高粘度有机溶剂混合,使本发明的苯胺衍生物溶解于其中的方法。
本发明中,对于电荷传输性清漆,从再现性良好地得到平坦性更高的薄膜的观点出发,希望使电荷传输性物质、掺杂剂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、真空中也能够得到具有均匀的成膜面和电荷传输性的薄膜,但如果考虑再现性良好地得到高电荷传输性薄膜,则优选大气气氛。
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、或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、或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元件中能够适宜地用作空穴注入层,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,优选在即将使用前进行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,进行烧成,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。也可以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。
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)-3,6-二甲苯基-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进行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-***)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'-二氟苯基吡啶合)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-***)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-***)二苯基甲基膦、锇(II)双 (3-(三氟甲基)-5-(2-吡啶基)-1,2,4-***)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-***)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)异喹啉]铱(III)等。
作为形成电子传输层/空穴阻挡层的材料,可列举出8-羟基喹啉锂、2,2',2”-(1,3,5-苯三基(benzenetriyl))-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-***、4-(萘-1-基)-3,5-二苯基-4H-1,2,4-***、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。
作为形成电子阻挡层的材料,可列举出三(苯基吡唑)铱等。
对使用了本发明的电荷传输性清漆的PLED元件的制作方法并无特别限定,可列举出以下的方法。
上述OLED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性高分子层、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PLED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,制成PLED元件。
作为使用的阴极和阳极材料,可以使用与上述OLED元件制作时同样的材料,可以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。
作为进行烧成的方法,可列举在非活性气体下或真空中、用烘箱或热板进行加热的方法。
应予说明,不仅是由上述说明的电荷传输性清漆得到的电荷传输性薄膜,而且由于由本发明的苯胺衍生物得到的蒸镀膜的电荷传输性也优异,因此可根据用途使用采用蒸镀法得到的电荷传输性薄膜。
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)1H-NMR:日本电子(株)制造JNM-ECP300FT NMR SYSTEM
(2)MALDI-TOF-MS:ブルカー社制造、autoflex III smartbeam
(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SURFCORDER ET-4000
(6)EL元件的制作:长州产业(株)制造、多功能蒸镀装置*** 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***
[1]化合物的合成
[制造例1]苯胺衍生物1的合成
[化13]
将联四苯胺1.50g、4-溴三苯基胺6.92g、Pd(dba)2 118mg、和叔丁氧基钠2.48g装入反应容器中,对容器内进行氮置换后,加入甲苯35mL、和另外预先准备的三-叔-丁基膦的甲苯溶液1.4mL(浓度:59g/L),在50℃下搅拌24小时。冷却到室温后,加入甲苯和饱和食盐水,进行分液。将有机层用无水硫酸钠干燥后,进行硅胶过滤,在得到的滤液中加入活性炭0.3g,在室温下搅拌1小时。通过过滤将活性炭除去,将滤液浓缩。将浓缩液滴入由醋酸乙酯300mL和甲醇300mL组成的混合溶剂中,将生成的浆液过滤。将得到的粉末干燥后,再次溶解于1,4-二噁烷约100mL中,滴入甲醇500mL中,将生成的浆液过滤。将得到的粉末干燥,得到了目标的苯胺衍生物1(4.90g,收率76%)。
1H-NMR(300MHz,THF-d8)δ[ppm]:7.17-7.22(m,20H),6.90-7.06(m,57H).
MALDI-TOF-MS m/Z测定:1582.47([M]+计算:1581.71).
[2]电荷传输性清漆的制备
[实施例1]
使作为电荷传输性物质的苯胺衍生物1的0.108g、作为掺杂剂物质的磷钨酸(PTA)0.202g和四氟四氰基醌二甲烷(F4TCNQ)0.094g 溶解于1,3-二甲基-2-咪唑啉酮(DMI)14.0g中。向其中加入2,3-丁二醇4.0g和丙二醇单甲基醚(PGME)2.0g,搅拌,进而向其中加入3,3,3-三氟丙基三甲氧基硅烷(信越化学工业(株)制造)0.007g和苯基三甲氧基硅烷(信越化学工业(株)制造)0.013g,搅拌,制备电荷传输性清漆。
[3]有机EL元件的制造和特性评价
[实施例2]
使用旋涂器将实施例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、150℃下烧成5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成膜为30nm。接下来,将CBP和Ir(PPy)3共蒸镀。就共蒸镀而言,控制蒸镀速率以使Ir(PPy)3的浓度成为6%,层叠40nm。接下来,依次层叠BAlq、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BAlq和铝,在0.2nm/秒的条件下进行,对于氟化锂,在0.02nm/秒的条件下进行,使膜厚分别为20nm、0.5nm和120nm。
应予说明,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元件用密封基板密封后,对其特性进行了评价。密封按照以下的程序进行。在氧浓度2ppm以下、露点-85℃以下的氮气氛中将有机EL元件收入密封基板之间,用粘接材料((株)MORESCO制造、モレスコモイスチャーカットWB90US(P))将密封基板贴合。此时,将捕水剂(ダイニック(株)制造,HD-071010W-40)与有机EL元件一起收入密封基板内。对于贴合的密封基板,照射UV光(波长:365nm、照射量:6,000mJ/cm2)后,在80℃下进行1小时退火处理,使粘接材料固化。
对于制作的元件,测定了驱动电流0.7mA下的驱动电压、亮度和发光效率。将结果示于表1。应予说明,各元件的发光面大小的面积为2mm×2mm。
[表1]
电压(V) | 亮度(cd/m<sup>2</sup>) | 发光效率(cd/A) | |
实施例2 | 9.29 | 4979 | 28.5 |
如表1中所示那样,可知具有由本发明的电荷传输性清漆得到了的电荷传输性薄膜作为空穴注入层的有机EL元件的亮度特性优异。
Claims (12)
1.苯胺衍生物,其特征在于,由式(1)表示:
式中,R1~R5表示氢原子,
Ph1相互独立地表示由式(P1)表示的基团,
式中,R6~R9表示氢原子,
Ar1表示由式(A5)表示的基团,
m为3。
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,上述掺杂剂物质包含卤代四氰基醌二甲烷化合物。
7.权利要求6所述的电荷传输性清漆,其中,上述掺杂剂物质还包含杂多酸。
8.电荷传输性薄膜,其使用权利要求4~7的任一项所述的电荷传输性清漆来制作。
9.电子设备,其具有权利要求8所述的电荷传输性薄膜。
10.有机电致发光元件,其具有权利要求8所述的电荷传输性薄膜。
11.电荷传输性薄膜的制造方法,其特征在于,在基材上涂布权利要求4~7的任一项所述的电荷传输性清漆,使溶剂蒸发。
12.权利要求1所述的苯胺衍生物的制造方法,其特征在于,在催化剂存在下使由式(2)表示的胺化合物与式(3)表示的芳基化合物反应,
式中,R1~R5、Ph1、和m表示与上述相同的含义,
Ar1-Z (3)
式中,Z表示卤素原子或拟卤素基,Ar1表示与上述相同的含义。
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