Nippon Steel & Sumikin Chemical Co., Ltd.

Nippon Steel Chemical Co., Ltd.

Megumi Matsumoto

Takahiro Kai

Toshihiro Yamamoto

Masaki Komori

Masanori Hotta

Yuichi Sawada

Junya Ogawa

Mitsuru Suda

Masashi Tada

Tohru Asari

Atsushi Kawada

Takaya Ishiyama

Hideki Tanaka

Yasuhisa Tsutsumi

Masana Jikumaru

Disclosed is an organic electroluminescent device (organic EL device) which is improved in luminous efficiency, sufficiently secures driving stability, and has a simple configuration. The organic EL device of this invention comprises a light-emitting layer between an anode and a cathode piled one upon another on a substrate wherein the light-emitting layer contains a phosphorescent dopant and a 1,9-substituted carbazole compound as a host material. An example of the 1,9-substituted carbazole compound is represented by the following general formula (1). In formula (1), Ar is an aromatic hydrocarbon group or aromatic heterocyclic group; L is an aromatic hydrocarbon group or aromatic heterocyclic group; each of Rto Ris a hydrogen atom, an alkyl group, a cycloalkyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group; n is an integer of 1 to 3.

Organic electroluminescent device

Provided is an organic electroluminescent device (EL device) that uses an indolocarbazole compound. The organic EL device includes an anode, a plurality of organic layers including a phosphorescent light-emitting layer, and a cathode laminated on a substrate, in which at least one organic layer selected from the phosphorescent light-emitting layer, a hole-transporting layer, an electron-transporting layer, and a hole-blocking layer contains an indolocarbazole compound represented by the general formula (1). In the general formula (1), a ring I and a ring II represent rings represented by the formula (1a) and the formula (1b), respectively, each of which are fused to an adjacent ring. X's each represent nitrogen or C&#x2014;Y and at least one of X's represents nitrogen. Y's each represent hydrogen, an alkyl group, a cycloalkyl group, or an aromatic group. A represents an alkyl group, a cycloalkyl group, or an aromatic group. At least one of Y and A represents an alkyl group or a cycloalkyl group. R's each represent hydrogen, an alkyl group, a cycloalkyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group.

Organic electroluminescent element

Provided is an organic electroluminescent device (organic EL device) which exhibits improved luminous efficiency, ensures sufficient driving stability, and has a simple configuration. The organic electroluminescent element includes an anode, a plurality of organic layers, and a cathode laminated on a substrate, and contains a carbazole compound represented by the general formula (1) in at least one layer selected from the group consisting of a emitting layer, a hole-transporting layer, and an electron-blocking layer. In general formula (1), L represents an m-valent aromatic hydrocarbon group or aromatic heterocyclic group, R's each represent hydrogen, an alkyl group, or a cycloalkyl group, m represents an integer of 1 to 3, and n's each represent an integer of 1 to 4, provided that at least one n represents an integer of 2 to 4, and at least one specific structure represented by the formula (1a) is present in the formula.

Provided are a novel nitrogen-containing aromatic heterocyclic compound and an organic electronic device using the compound. Specifically provided is an organic electroluminescent device, including a plurality of organic layers between an anode and a cathode laminated on a substrate, in which at least one of the organic layers contains a nitrogen-containing aromatic compound represented by the following formula (1). In the formula, L represents an n+m-valent group arising from an alkane, a cycloalkane, an aromatic hydrocarbon, an aromatic heterocyclic compound, a triarylamine, or a diarylsulfone, A represents an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a silyl group, an acyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group, X represents C(R), oxygen, S, or Se, R represents H, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group, m represents an integer of 1 to 4, and n represents an integer of 0 to 3. The total number of m and n is 2 to 4. 

Disclosed is an organic electroluminescent device (organic EL device) which is improved in luminous efficiency, sufficiently secures driving stability, and has a simple configuration. The organic EL device of this invention comprises a light-emitting layer between an anode and a cathode piled one upon another on a substrate and the light-emitting layer contains a phosphorescent dopant and an unsymmetrical indolocarbazole compound as a host material. The unsymmetrical indolocarbazole compound has a structure in which two or more groups having an indolocarbazole structure are linked together by a linking group and at least one of the groups has an isomeric indolocarbazole skeleton different from those of the other groups. Examples of the unsymmetrical indolocarbazole compound include compounds represented by the following formula (2) wherein A is a substituent, each of Rto Ris a hydrogen atom or a substituent, and L is a linking group composed of an aromatic group. 

Provided are a novel chalcogen-containing aromatic compound and an organic electronic device using the compound. This compound is a chalcogen-containing aromatic compound represented by the formula (1). Among the organic electronic devices each using this chalcogen-containing aromatic compound are an organic EL device, an organic TFT device, a photovoltaic device, and the like. In the formula (1): X represents oxygen, sulfur, or selenium; A represents an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group, an aromatic heterocyclic group, or an amino group; and n's each independently represent an integer of 0 to 2, provided that a sum of two n's is 1 to 4. 

Chalcogen-containing aromatic compound, organic semiconductor material, and organic electronic device

Disclosed is an organic electroluminescent device (organic EL device) that is improved in luminous efficiency, sufficiently secures driving stability, and has a simple configuration. This organic EL device is constituted of an anode, organic layers comprising a phosphorescent light-emitting layer, and a cathode piled one upon another on a substrate and at least one organic layer selected from a light-emitting layer, an electron-transporting layer, and a hole-blocking layer contains an indolocarbazole compound represented by general formula (1). In the case where the indolocarbazole compound is incorporated in the light-emitting layer containing a phosphorescent dopant and a host material, it is incorporated as the host material. Some of such indolocarbazole compounds are represented by the following formula (2): wherein each of Aand Ais an aromatic hydrocarbon group; each of Band Bis an aromatic heterocyclic group; each of Rto Ris a hydrogen atom, an alkyl group, a cycloalkyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group; m is an integer of 1 to 3; and n is an integer of 0 to 3. 

Organic electroluminescent device comprising an organic layer containing an indolocarbazole compound

Disclosed is an organic electroluminescent device (organic EL device) that is improved in luminous efficiency, sufficiently secures driving stability, and has a simple configuration. This organic EL device has a light-emitting layer between an anode and a cathode piled one upon another on a substrate and the said light-emitting layer contains a fused polycyclic compound in which seven or more rings are fused together as a host material. The aforementioned fused polycyclic compound has a structure formed by fusing two or more indole rings to a carbazole ring. A specific example thereof is the compound represented by the following formula.

Provided is an organic electroluminescent device (organic EL device) that is improved in luminous efficiency, sufficiently secures driving stability, and has a simple configuration. The device comprises a plurality of organic layers between an anode and a cathode piled one upon another on a substrate wherein at least one of the organic layers contains a nitrogen-containing organic compound represented by the following formula (1). In formula (1), X is N-A, an oxygen atom, or a sulfur atom; A is an alkyl group, a cycloalkyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group; and R is a hydrogen atom, an alkyl group, a cycloalkyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group.

Disclosed is an organic electroluminescent device (organic EL device) that is improved in luminous efficiency, sufficiently secures driving stability, and has a simple configuration. This organic EL device comprises organic layers between an anode and a cathode piled one upon another on a substrate and at least one organic layer selected from a light-emitting layer, a hole-transporting layer, an electron-transporting layer, and a hole-blocking layer contains a carbazole compound represented by the following formula (1). In the case where the light-emitting layer of the organic electroluminescent device contains a phosphorescent dopant and a host material, it is the carbazole compound that is contained as the host material. In formula (1), X is C&#x2014;Y or a nitrogen atom; Y is a hydrogen atom, an alkyl group, a cycloalkyl group, or an aromatic group; n is an integer of 2 to 4: A is an n-valent aromatic group; L is a direct bond or a divalent aromatic group; and R is a hydrogen atom, an alkyl group, or a cycloalkyl group.

Provided are a nitrogen-containing aromatic heterocyclic compound useful as an organic semiconductor material and an organic electronic device using this compound. The nitrogen-containing aromatic heterocyclic compound has a fused indole skeleton represented by the following formula (1), the organic semiconductor material contains the compound, and the organic electronic device uses the organic semiconductor material. In general formula (1), X is N-A', O, S, or Se; A is an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group exclusive of a fused heterocycle consisting of 4 rings or more; and R is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group exclusive of a fused heterocycle consisting of 4 rings or more.

Nitrogen-containing aromatic compound, organic semiconductor material, and organic electronic device

Provided are a novel nitrogen-containing aromatic heterocyclic compound and an organic electronic device using the compound. This nitrogen-containing aromatic compound is represented by the general formula (1). Further, the present invention relates to organic electronic devices such as a light-emitting device, a thin-film transistor, and a photovoltaic device each using the nitrogen-containing aromatic compound. (L represents an m+n-valent aromatic hydrocarbon group or aromatic heterocyclic group, or a group arising from a triarylamine or a diaryl sulfone; X represents N-A, O, S, or Se; A represents an alkyl group or the like; R represent hydrogen, an alkyl group, an aromatic group, or the like; and m+n is an integer of 2 to 4.)

Nitrogenated aromatic compound, organic semiconductor material, and organic electronic device

Disclosed is an organic electroluminescent device (organic EL device) which is improved in luminous efficiency, fully secured of high driving stability, and of a simple structure. The organic EL device is constituted of an anode, organic layers containing a phosphorescent light-emitting layer, and a cathode piled one upon another on a substrate and a phosphine oxide derivative represented by general formula (1) is contained in a phosphorescent light-emitting layer, an electron-transporting layer, a hole-blocking layer, or an exciton-blocking layer. In general formula (1), Lis a direct bond or an aromatic group with a valence of 1-3 and Aris an aromatic group. The two Argroups linked to the same nitrogen atom may form a nitrogen heterocycle and may further form a fused ring together with the said nitrogen heterocycle. 

Provided is an organic electroluminescent device (organic EL device), in which the luminous efficiency of the device is improved, driving stability is sufficiently ensured, and the construction of the device is simple. This organic EL device is an organic electroluminescent device, including a light-emitting layer between an anode and a cathode laminated on a substrate, in which the light-emitting layer contains a phosphorescent light-emitting dopant and an indolocarbazole compound as a host material. Examples of the indolocarbazole compound include a compound represented by the following formula (1). It should be noted that in the formulae: a ring A and a ring B are represented by the formulae (1a) and (1b), respectively; Ar's each represent an aromatic hydrocarbon group or an aromatic heterocyclic group; R's each represent a hydrogen atom, an alkyl group, or a cycloalkyl group; X represents a methine group or a nitrogen atom; A represents an aromatic hydrocarbon group, an alkyl group, a cycloalkyl group, or a group represented by the formula (1c); and n represents 0 or 1.

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Kitakyushu, Japan

Megumi Matsumoto