Hodogaya Chemical Co., Ltd.

Sfc Co., Ltd.

Kouki Kase

Kazuyuki Suruga

Takeshi Yamamoto

Shuichi Hayashi

Shunji Mochizuki

Yuta Hirayama

Norimasa Yokoyama

Eiji Takahashi

Se-Jin Lee

Si-In Kim

Shigeru Kusano

Naoaki Kabasawa

Soon-Wook Cha

Makoto Nagaoka

Kazunori Togashi

Takuya Uehara

Daizou Kanda

Ji-Hwan Kim

Sung-Hoon Joo

Shunji Mochiduki

Junichi Izumida

Seok-Bae Park

Ji-Yung Kim

Shingo Ozawa

Young-Tae Choi

Hiroshi Ohkuma

Teruaki Koizumi

Kyung-Hwa Park

Su-Jin Lee

Eriko Chiba

Jae-Geon Lim

Byung-Sun Yang

It is an object of the present invention to provide, as a material for organic EL device having high efficiency and high durability, an organic compound having excellent characteristics such as excellent electron injection/transport performance, hole blocking performance, and high stability in a film state, and an organic EL device having high efficiency and high durability, which is obtained by using this compound. A compound having a pyrimidine ring structure, the compound being represented by the following general formula (1). (In the formula, Arepresents a substituted or unsubstituted aromatic heterocyclic group. Arrepresents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted fused polycyclic aromatic group. Arrepresents a deuterium atom, a trimethylsilyl group, a triphenylsilyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted fused polycyclic aromatic group. m represents an integer of 1 to 3, n represents an integer of 0 to 2, and o represents an integer of 1 to 2. In a case where m is an integer of two or more, a plurality of Arbonded to the same pyrimidine ring may be the same or different from each other. In a case where n is an integer of two, a plurality of Arbonded to the same pyrimidine ring may be the same or different from each other. In a case where o is an integer of two, a plurality of Abonded to the same pyrimidine ring may be the same or different from each other. However, the sum of the integers of m, n, and o is 4 or less. Note that in a case where n is 0, Arrepresents a hydrogen atom.)

Compound having pyrimidine ring structure and organic electroluminescence device

An object of the present invention is to provide, as a material for a highly efficient and highly durable organic EL element, an organic compound that has excellent properties, including excellent electron-injecting/transporting capability, hole-blocking capability, and high stability in the form of a thin film. Another object of the present invention is to provide a highly efficient and highly durable organic EL element by using this compound. The present invention focuses on the properties of the benzazole ring, which has affinity for electrons, and specifically focuses on the capability of its nitrogen atom to coordinate to a metal and also on excellent heat resistance. The inventors have thus designed and chemically synthesized various compounds having a benzazole ring structure, and then experimentally produced organic EL elements including the compounds, followed by thoroughly evaluating the characteristics thereof. As a result, it has been found that it is possible to obtain an organic EL element having excellent properties by using a specific compound having a benzazole ring structure.

Compound having benzazole ring structure, and organic electroluminescent device

A compound including a benzimidazole ring structure, represented by general formula (1). (In formula (1), Xand Xmay be the same or different and each represent a specific carbon atom or a nitrogen atom, Ar represents a specific group, Rand Rmay be the same or different and each represent a specific group, and m is an integer of 0-4.)

Compound including benzimidazole ring structure and organic electroluminescent element

An object of the present invention is to provide, as a material for a highly efficient and highly durable organic EL element, an organic compound having excellent properties, including excellent electron-injecting/transporting capability, hole-blocking capability, and high stability in the form of a thin film. Another object of the present invention is to provide a highly efficient and highly durable organic EL element by using this compound. The compound having an azabenzoxazole ring structure of the present invention has excellent heat resistance, and good electron-transporting capability. An organic EL element having an electron-transporting layer, a hole-blocking layer, a light-emitting layer, or an electron-injecting layer including the compound had favorable element characteristics.

Compound having azabenzoxazole ring structure and organic electroluminescent element

The present disclosure is related to an organic EL element including a capping layer that contains a compound represented by formula (A-1). In the formula, A and X are monovalent groups represented by formula (B-1) having 1 binding site among Rto R. Z represents a monovalent group represented by formula (B-1) having 1 binding site among Rto R, an aromatic hydrocarbon group, an aromatic heterocyclic group or a fused polycyclic aromatic group. Ar is a single bond or a divalent group of an aromatic hydrocarbon group, an aromatic heterocyclic group, or a fused polycyclic aromatic group. Rto Rare each defined in the specification, and Q represents a nitrogen atom, an oxygen atom, or a sulfur atom.

Organic electroluminescent element and method for producing same

The present invention relates to an organic EL device having at least an anodic electrode, a hole transport layer, a light emitting layer, an electron transport layer, a cathodic electrode, and a capping layer in this order, in which the capping layer contains an amine compound having a benzazole ring structure represented by the following general formula (A-1).

Organic EL device, amine compound having benzazole ring structure, and method in which said amine compound is used in capping layer of organic EL device

An object of the present invention is to provide an organic compound that has excellent properties, with excellent hole injection and transport performance, electron blocking capability, and high stability in a thin film state, and furthermore to provide a highly efficient and highly durable organic EL device by using this compound. The present invention relates to a compound having a triarylamine structure and being represented by the structural formula (A-1) below, where A, B, and C may be the same or different, and each represent a group represented by the structural formula (B-1) below, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted fused polycyclic aromatic group, where at least one of A, B, and C is not the group represented by the structural formula (B-1) below. (For the symbols and the like in the formulae, see the descriptions in the specification.)

Compound having triarylamine structure and organic electroluminescence device

To provide an organic EL device having low driving voltage, high luminous efficiency, and particularly a long lifetime by combining various materials for an organic EL device having excellent hole and electron injection/transport performances, electron blocking ability, stability in a thin-film state, and durability as materials for an organic EL device having high luminous efficiency and high durability so as to allow the respective materials to effectively reveal their characteristics. In the organic EL device having at least an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode, in this order, the hole injection layer includes an arylamine compound of the following general formula (1) and a radialene derivative of the following general formula (2).

Organic electroluminescent device

The present disclosure is related to an organic EL element including a capping layer that contains a compound represented by formula (A-1). In the formula, A and X are monovalent groups represented by formula (B-1) having 1 binding site among Rto R. Z represents a monovalent group represented by formula (B-1) having 1 binding site among Rto R, an aromatic hydrocarbon group, an aromatic heterocyclic group or a fused polycyclic aromatic group. Ar is a single bond or a divalent group of an aromatic hydrocarbon group, an aromatic heterocyclic group, or a fused polycyclic aromatic group. Rto Reach represent a linking group as a binding site, a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group, a cycloalkyl group, an alkenyl group, an alkyloxy group, a cycloalkyloxy group, an aromatic hydrocarbon group, an aromatic heterocyclic group, a fused polycyclic aromatic group, or an aryloxy group. Q represents a nitrogen atom, an oxygen atom, or a sulfur atom.

An organic EL device is provided, including at least an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode in this order, wherein the hole transport layer contains an arylamine compound represented by the following formula (1), wherein Arto Arand n1 are defined in the specification, and the electron transport layer contains a compound having a benzoazole ring structure represented by the following formula (2), wherein Ar, Ar, X, Y, Zand Zare defined in the specification.  

Organic electroluminescence device

It is an object of the present invention to provide an organic EL device in which, as a highly efficient and highly durable organic EL material, various materials excelling in electron injection/transport performance, hole blocking performance, hole resistance performance, exciton confinement performance, stability in a film state, and durability, are combined so that properties of each material can be effectively demonstrated, thereby achieving (1) high light emission efficiency and power efficiency, (2) low luminescence starting voltage, (3) low practical driving voltage, and (4) particularly long lifetime. An organic EL device including at least a anode, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and a cathode in this order, characterized in that the hole blocking layer includes a compound having a benzoazole structure represented by the following general formula (1). (In the formula, Arand Armay be the same or different from each other and each represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted fused polycyclic aromatic group, or a substituted or unsubstituted aromatic heterocyclic group. Yrepresents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted fused polycyclic aromatic group, a substituted or unsubstituted aromatic heterocyclic group, a straight-chained or branched alkyl group that has 1 to 6 carbon atoms and may have a substituent group, a cycloalkyl group that has 5 to 10 carbon atoms and may have a substituent group, or a straight-chained or branched alkenyl group that has 2 to 6 carbon atoms and may have a substituent group. X represents an oxygen atom or a sulfur atom. Zand Zmay be the same or different from each other and each represent a carbon atom or a nitrogen atom).

Organic electroluminescence device that includes compound having benzoazole structure

An aryldiamine compound represented by formula (1) and an organic electroluminescent device including a pair of electrodes and at least one organic layer disposed therebetween wherein the at least one organic layer contains the aryldiamine compound. The aryldiamine compound is excellent in hole transporting properties, hole injection properties, electron blocking properties, stability in thin film form, and heat resistance. The organic electroluminescent device achieves high emission efficiency and power efficiency, drives at a low voltage, and, in particular, has a long life. 

Aryldiamine compound and organic electroluminescent element

According to the present invention, there are provided a benzopyridoindole derivative represented by the following general formula (1); and an organic EL element including a pair of electrodes and at least one organic layer sandwiched therebetween, wherein the above derivative is used as a constituent material for the at least one organic layer. The benzopyridoindole derivative of the present invention is excellent in electron injection/transport performance, has hole blocking capability, is highly stable in a thin film state, and excels in various characteristics. Thus, it is useful as a material for an organic EL element with a high efficiency, a low driving voltage, and high durability. 

Benzopyridoindole derivative and organic electroluminescent element

An organic compound with excellent characteristics excelling in hole-injecting/transporting performance and having electron blocking ability, high stability in a thin-film state and high luminous efficiency is provided as material for an organic electroluminescent device. The compound of a general formula () having an indenocarbazole ring structure is used as a constituent material of at least one organic layer in the organic electroluminescent device that includes a pair of electrodes and one or more organic layers sandwiched between the pair of electrodes. 

Compound having indenocarbazole ring structure, and organic electroluminescent device

There is provided an organic compound of excellent characteristics that exhibits excellent hole-injecting/transporting performance and has an electron blocking ability and a highly stable thin-film state with excellent heat resistance. The compound of the present invention is an arylamine compound having a triphenylamine structure. The arylamine compound is used as a constituent material of at least one organic layer in an organic electroluminescent device that includes a pair of electrodes, and one or more organic layers sandwiched between the pair of electrodes.

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Tokyo, Japan

Kouki Kase