申请人:Ciba Specialty Chemicals Holding Inc.
公开号:EP1087006A1
公开(公告)日:2001-03-28
Electroluminescent device comprising in this order
(a) an anode
(b) a hole transporting layer
(c) a light-emitting layer
(d) optionally an electron transporting layer and
(e) a cathode
and a light-emitting substance, wherein the light-emitting substance is a diketopyrrolopyrrole represented by formula I or formula III
wherein R1 and R2, independently from each other, stand for C1-C25-alkyl, allyl which can be substituted one to three times with C1-C3alkyl or Ar3, or -CR3R4-(CH2)m-Ar3, wherein R3 and R4 independently from each other stand for hydrogen or C1-C4alkyl, or phenyl which can be substituted one to three times with C1-C3 alkyl,
Ar3 stands for phenyl or 1- or 2-naphthyl which can be substituted one to three times with C1-C8alkyl, C1-C8alkoxy, halogen or phenyl, which can be substituted with C1-C8alkyl or C1-C8alkoxy one to three times, and m stands for 0, 1, 2, 3 or 4,
Ar1 and Ar2, independently from each other, stand for aryl radicals, preferably for
or
or
wherein
R5, R6 and R7, independently from each other, stand for hydrogen, cyano, halogen, C1-C6alkyl, -NR8R9, -OR10, -S(O)nR8, -Se(O)nR8, or phenyl, which can be substituted one to three times with C1-C8alkyl or C1-C8alkoxy,
wherein R8 and R9, independently from each other, stand for hydrogen, phenyl, C1-C25-alkyl, C5-C12-cycloalkyl, -CR3R4-(CH2)m-Ph, R10, wherein R10 stands for C6-C24-aryl, or a saturated or unsaturated heterocyclic radical comprising five to seven ring atoms, wherein the ring consists of carbon atoms and one to three hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein Ph, the aryl and heterocyclic radical can be substituted one to three times with C1-C8alkyl, C1-C8alkoxy, or halogen, or R8 and R9 stand for -C(O)R10, wherein R11 can be C1-C25-alkyl, C5-C12-cycloalkyl, R10, -OR12 or -NR13R14, wherein R12, R13, and R14 stand for C1-C25-alkyl, C5-C12-cycloalkyl, C6-C24-aryl, or
a saturated or unsaturated heterocyclic radical comprising five to seven ring atoms, wherein the ring consists of carbon atoms and one to three hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein the aryl and heterocyclic radical can be substituted one to three times with C1-C8alkyl or C1-C8alkoxy, or -NR8R9 stands for a five- or sixmembered heterocyclic radical in which R8 and R9 together stand for tetramethylene, pentamethylene, -CH2-CH2-O-CH2-CH2-, or -CH2-CH2-NR5-CH2-CH2-, preferably -CH2-CH2-O-CH2-CH2-, and n stands for 0, 1, 2 or 3,
and wherein Z stands for a diradical selected from the group consisting of a single bond, C2-C6alkylene, which can be substituted one to three times with C1-C4alkyl, C1-C4alkoxy, or phenyl, phenylene or naphthylene, processes for the preparation of compounds I, its uses and compositions comprising the compounds I and/or III.
电致发光装置依次包括
(a) 阳极
(b) 空穴传输层
(c) 发光层
(d) 可选的电子传输层和
(e) 阴极
和一种发光物质,其中发光物质是由式 I 或式 III 表示的二酮吡咯啉
其中 R1 和 R2 独立地代表 C1-C25 烷基、可被 C1-C3 烷基或 Ar3 取代一至三次的烯丙基,或 -CR3R4-(CH2)m-Ar3,其中 R3 和 R4 独立地代表氢或 C1-C4 烷基,或可被 C1-C3 烷基取代一至三次的苯基、
Ar3 代表苯基或 1-或 2-萘基,可被 C1-C8烷基、C1-C8烷氧基、卤素或苯基取代 1 至 3 次,后者可被 C1-C8 烷基或 C1-C8 烷氧基取代 1 至 3 次,m 代表 0、1、2、3 或 4、
Ar1 和 Ar2 各自代表芳基,最好为
或
或
其中
R5、R6 和 R7 相互独立地代表氢、氰基、卤素、C1-C6烷基、-NR8R9、-OR10、-S(O)nR8、-Se(O)nR8 或苯基,苯基可被 C1-C8 烷基或 C1-C8 烷氧基取代一至三次、
其中 R8 和 R9 各自代表氢、苯基、C1-C25-烷基、C5-C12-环烷基、-CR3R4-(CH2)m-Ph、R10(其中 R10 代表 C6-C24-芳基)或由 5 至 7 个环原子组成的饱和或不饱和杂环基,其中环由碳原子和 1 至 3 个选自氮组成的杂原子组成、其中 Ph、芳基和杂环基可被 C1-C8烷基、C1-C8烷氧基或卤素取代一至三次,或 R8 和 R9 代表-C(O)R10,其中 R11 可以是 C1-C25-烷基、C5-C12-环烷基、R10、-OR12 或-NR13R14,其中 R12、R13 和 R14 代表 C1-C25-烷基、C5-C12-环烷基、C6-C24-芳基或饱和或不饱和杂环基。
由五至七个环原子组成的饱和或不饱和杂环基,其中环由碳原子和一至三个选自氮、氧和硫的杂原子组成,其中芳基和杂环基可被 C1-C8 烷基或 C1-C8 烷氧基取代一至三次、或 -NR8R9 代表五元或六元杂环基,其中 R8 和 R9 分别代表四亚甲基、五亚甲基、-CH2-CH2-O-CH2-CH2-或 -CH2-CH2-NR5-CH2-CH2-,最好是 -CH2-CH2-O-CH2-CH2-,n 代表 0、1、2 或 3、
其中 Z 代表选自由单键、可被 C1-C4 烷基、C1-C4 烷氧基或苯基、亚苯基或亚萘基取代 1 至 3 次的 C2-C6 烷基、化合物 I 的制备工艺、其用途和包含化合物 I 和/或 III 的组合物组成的组中的二叉。