COMPOUND HAVING INDENOCARBAZOLE RING STRUCTURE, AND ORGANIC ELECTROLUMINESCENT ELEMENT
申请人:Hodogaya Chemical Co., Ltd.
公开号:EP3709375A1
公开(公告)日:2020-09-16
[Object] It is an object of the present invention to provide an organic compound having excellent properties such as excellent hole injection/transport performance, electron blocking performance, high stability in a thin-film state, and high light emission efficiency as a material for a highly efficient organic EL device having a high durability, and a highly efficient organic EL device having a high durability by using this compound.
[Solving Means] An organic EL device, including, between an anode and a cathode, at least a first hole transport layer, a second hole transport layer, a green light-emitting layer, and an electron transport layer in the stated order from a side of the anode, the organic EL device being characterized in that the second hole transport layer, or at least one of stacked films disposed between the first hole transport layer and the electron transport layer contains a compound having an indenocarbazole ring structure, the compound being represented by the following general formula (1).
(In the formula, A represents a divalent group of a substituted or unsubstituted aromatic hydrocarbon, a divalent group of a substituted or unsubstituted aromatic heterocycle, or a divalent group of a substituted or unsubstituted fused polycyclic aromatic. Ar1, Ar2, and Ar3 may be the same as or different from each other, and each represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted fused polycyclic aromatic group. Here, A and Ar2 or Ar2 and Ar3 may form a ring with a single bond or may be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring. R1 to R9 may be the same as or different from each other, each represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituted group, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituted group, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituted group, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituted group, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituted group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, and may form a ring with a single bond or may be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring. R10 and R11 may be the same as or different from each other, each represent a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituted group, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituted group, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituted group, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituted group., a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituted group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, and may form a ring with a single bond or may be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring.)
[目的]本发明的目的是提供一种具有优异性能的有机化合物,例如优异的空穴注入/传输性能、电子阻断性能、薄膜状态下的高稳定性和高光发射效率,作为具有高耐用性的高效有机电致发光器件的材料,并通过使用该化合物提供一种具有高耐用性的高效有机电致发光器件。
[解决手段]一种有机电致发光器件,在阳极和阴极之间,从阳极一侧按所述顺序至少包括第一空穴传输层、第二空穴传输层、绿色发光层和电子传输层,该有机电致发光器件的特征在于,第二空穴传输层或设置在第一空穴传输层和电子传输层之间的叠层薄膜中的至少一层含有具有
茚并
咔唑环结构的化合物,该化合物由以下通式(1)表示。
(式中,A 代表取代或未取代的
芳香烃的二价基团,取代或未取代的芳香杂环的二价基团,或取代或未取代的融合多环芳香的二价基团。Ar1、Ar2 和 Ar3 可以彼此相同或不同,各自代表取代或未取代的
芳香烃基团、取代或未取代的芳香杂环基团或取代或未取代的融合多环芳香基团。这里,A 和 Ar2 或 Ar2 和 Ar3 可以通过单键形成一个环,也可以通过取代或未取代的亚甲基、氧原子或
硫原子相互键合形成一个环。R1 至 R9 可彼此相同或不同,各自代表氢原子、
氘原子、
氟原子、
氯原子、
氰基、硝基、具有 1 至 6 个碳原子且可能具有取代基的直链或支链烷基、具有 5 至 10 个碳原子且可能具有取代基的环烷基、具有 2 至 6 个碳原子且可能具有取代基的直链或支链烯基、具有 1 至 6 个碳原子且可能具有取代基的直链或支链烷氧基、具有 5 至 10 个碳原子且可能具有取代基团的环烷氧基、取代或未取代的
芳香烃基、取代或未取代的芳香杂环基、取代或未取代的融合多环芳香基,或取代或未取代的芳氧基,并可通过单键形成环,或通过取代或未取代的亚甲基、氧原子或
硫原子相互键合形成环。R10 和 R11 可彼此相同或不同,各自代表一个具有 1 至 6 个碳原子且可能具有取代基的直链或支链烷基、一个具有 5 至 10 个碳原子且可能具有取代基的环烷基、一个具有 2 至 6 个碳原子且可能具有取代基的直链或支链烯基、一个具有 1 至 6 个碳原子且可能具有取代基的直链或支链烷氧基、具有 5 至 10 个碳原子且可带有取代基的环烷氧基、取代或未取代的
芳香烃基、取代或未取代的芳香杂环基、取代或未取代的融合多环芳香基、取代或未取代的芳氧基,可通过单键形成环,也可通过取代或未取代的亚甲基、氧原子或
硫原子相互键合形成环)。