Hodogaya Chemical Co., Ltd.

Mitsubishi Paper Mills Limited

Sfc Co., Ltd.

Kazuyuki Suruga

Kouki Kase

Takeshi Yamamoto

Shunji Mochizuki

Shuichi Hayashi

Yuta Hirayama

Si-In Kim

Naoaki Kabasawa

Tamotsu Horiuchi

Se-Jin Lee

Soon-Wook Cha

Makoto Nagaoka

Bong-Ki Shin

Ji-Hwan Kim

Makoto Okaji

Sung-Hoon Joo

Keigo Naito

Oun-Gyu Lee

Hiroshi Ookuma

Michihiko Sato

Ji-Yung Kim

Su-Jin Lee

Eriko Chiba

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

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

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.

There is provided an organic electroluminescence device, including at least an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode in the stated order, the organic electroluminescence device being characterized in that the hole transport layer contains an arylamine compound represented by formula (1), and the light-emitting layer contains a heterocyclic compound having a fused ring structure represented by formula (2) or a heterocyclic compound having a fused ring stricture represented by formula (3), wherein each of formulas (1), (2) and (3) are set forth in the specification.

Organic electroluminescence device

To provide a material for an organic EL device that is excellent in hole injection and transport abilities, electron blocking ability, thin film stability, and durability, as a material for an organic EL device with high efficiency and high durability, and also to provide an organic EL device having a high efficiency, a low driving voltage, and a long lifetime by combining the material with various materials for an organic EL device that is excellent in hole and electron injection and transport abilities, electron blocking ability, thin film stability, and durability. An organic electroluminescent device comprising 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 comprises a carbazole compound of the following general formula (1), and the light emitting layer comprises a blue light emitting dopant. 

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.  

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

To provide an organic EL device having (1) high luminous efficiency and high power efficiency, (2) low turn on voltage, (3) low actual driving voltage, and (4) a long lifetime, by combining various materials for an organic EL device, which are excellent in hole injection/transport performances, electron injection/transport performances, electron blocking ability, stability in a thin-film state, and 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 transport layer, a light emitting layer, an electron transport layer and a cathode in this order, the hole transport layer includes an arylamine compound of the following general formula (1), and the electron transport layer includes a compound of the following general formula (2) having a benzazole ring structure. 

Oxytitanium phthalocyanine having a novel crystal form having excellent electrophotographic properties, such as a high charge potential, a high sensitivity and stable performances free from causing changes in various properties in repeated use, can be produced in the absence of a halogen substance, by carrying out the crystal transformation of amorphous oxytitanium phthalocyanine in a solvent comprising water and naphthalene.

Growing community of inventors

Tokyo, Japan

Kazuyuki Suruga