公开(公告)号：US20140124764A1

公开(公告)日：2014-05-08

申请号：US14068319

申请日：2013-10-31

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Yasushi Kitano ,  Hiroshi Kadoma ,  Satoko Shitagaki ,  Satoshi Seo ,  Hiromi Seo ,  Tatsuyoshi Takahashi

IPC: H01L51/00

CPC classification number: H01L51/0072 ,  C07D209/86 ,  C07D405/10 ,  C09K11/06 ,  C09K2211/1416 ,  C09K2211/1425 ,  C09K2211/145 ,  C09K2211/1458 ,  H01L51/0073

Abstract: To provide a novel heterocyclic compound capable of being used as a host material in which a light-emitting substance is dispersed. To provide a light-emitting element having a long lifetime. A heterocyclic compound in which a dibenzo[f,h]quinoxalinyl group and a benzo[b]naphtho[1,2-d]furanyl group are bonded through an arylene group having 6 to 13 carbon atoms. The dibenzo[f,h]quinoxalinyl group, the benzo[b]naphtho[1,2-d]furanyl group, and the arylene group separately are unsubstituted or have, as a substituent, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 13 carbon atoms.

Abstract translation: 提供能够用作其中分散有发光物质的主体材料的新型杂环化合物。 提供寿命长的发光元件。 其中二苯并[f，h]喹喔啉基和苯并[b]萘并[1,2-d]呋喃基通过具有6至13个碳原子的亚芳基键合的杂环化合物。 二苯并[f，h]喹喔啉基，苯并[b]萘并[1,2-d]呋喃基和亚芳基分别是未取代的或具有取代基的具有1至4个碳原子的烷基或 具有6至13个碳原子的芳基。

公开(公告)号：US10468602B2

公开(公告)日：2019-11-05

申请号：US15704137

申请日：2017-09-14

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Yasushi Kitano ,  Hiromi Seo ,  Tatsuyoshi Takahashi ,  Satoshi Seo

IPC: H01L51/00 ,  C07D241/38 ,  C09K11/06 ,  H01L51/50

Abstract: A novel heterocyclic compound is provided. A novel heterocyclic compound that can be used for a light-emitting element is provided. A novel heterocyclic compound that can improve the reliability of a light-emitting element when used for a light-emitting element is provided. A light-emitting element, a light-emitting device, an electronic appliance, or a lighting device which includes the novel heterocyclic compound and is highly reliable is provided. One embodiment of the present invention is a heterocyclic compound represented by a general formula (G0). In the general formula (G0), A represents a dibenzo[f,h]quinoxalinyl group, B represents a substituted or unsubstituted fluorenyl group, and Ar represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms. A-Ar—B   (G0)

公开(公告)号：US20130323869A1

公开(公告)日：2013-12-05

申请号：US13905720

申请日：2013-05-30

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Yasushi Kitano ,  Takao Hamada ,  Satoshi Seo ,  Hiroki Suzuki ,  Tomohiro Kubota

IPC: H01L51/00

CPC classification number: H01L51/0072 ,  H01L51/006 ,  H01L51/0074 ,  H01L51/0085 ,  H01L2251/308

Abstract: A novel organic material with fewer impurities, a light-emitting element including the organic material, and a light-emitting device, an electronic appliance, and a lighting device each of which includes the light-emitting element are provided. The organic material is obtained by coupling an aryl halide and an aryl boronic acid or an aryl boronic acid ester. The aryl boronic acid or the aryl boronic acid ester includes at least one of a first impurity in which a boryl group of the aryl boronic acid or the aryl boronic acid ester is substituted by hydrogen and a second impurity in which a molecular mass of 16 or 17 is added to the molecular mass of the first impurity. The concentration of an impurity other than the first impurity and the second impurity is 1% or lower.

Abstract translation: 提供了具有较少杂质的新型有机材料，包括有机材料的发光元件，以及包括发光元件的发光装置，电子设备和照明装置。 有机材料通过偶合芳基卤和芳基硼酸或芳基硼酸酯而获得。 芳基硼酸或芳基硼酸酯包括其中芳基硼酸或芳基硼酸酯的硼基被氢取代的第一杂质和第二杂质中的至少一种，其中分子量为16或 17添加到第一杂质的分子量。 除了第一杂质和第二杂质以外的杂质的浓度为1％以下。

公开(公告)号：US12127479B2

公开(公告)日：2024-10-22

申请号：US18381846

申请日：2023-10-19

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Satoshi Seo ,  Takao Hamada ,  Tatsuyoshi Takahashi ,  Yasushi Kitano ,  Hiroki Suzuki ,  Hideko Inoue

IPC: H01L51/50 ,  C07D403/14 ,  H10K85/60 ,  H10K85/30

CPC classification number: H10K85/6572 ,  C07D403/14 ,  H10K85/342 ,  H10K85/633 ,  H10K85/636 ,  Y02P20/582

Abstract: To provide a light-emitting element with an improved reliability, a light-emitting element with a high current efficiency (or a high quantum efficiency), and a novel dibenzo[f,h]quinoxaline derivative that is favorably used in a light-emitting element which is one embodiment of the present invention. A light-emitting element includes an EL layer between an anode and a cathode. The EL layer includes a light-emitting layer; the light-emitting layer contains a first organic compound having an electron-transport property and a hole-transport property, a second organic compound having a hole-transport property, and a light-emitting substance; the combination of the first organic compound and the second organic compound forms an exciplex; the HOMO level of the first organic compound is lower than the HOMO level of the second organic compound; and a difference between the HOMO level of the first organic compound and the HOMO level of the second organic compound is less than or equal to 0.4 eV.

公开(公告)号：US11090577B2

公开(公告)日：2021-08-17

申请号：US16090914

申请日：2017-03-30

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Sachiko Kawakami ,  Yasushi Kitano ,  Kanata Abe

IPC: B01D7/02 ,  B01D7/00 ,  B01D1/14 ,  C07B63/00 ,  C09K11/06 ,  H01L51/00 ,  H01L51/50 ,  H01L51/56 ,  H01L51/52

Abstract: A novel sublimation purification method is provided. Moreover, a novel sublimation purification apparatus is provided. A purification method using a purification apparatus including a purification portion where a substance is purified by vaporization, a temperature adjustment means, a gas supply means, and a gas discharge means is provided. In the purification method, the inside of the purification portion is made to have a first pressure with use of the gas discharge means, a temperature gradient is generated in the purification portion with use of the temperature adjustment means such that the substance is purified, the pressure in the purification portion is then set at a second pressure with use of the gas supply means, and the purification portion is cooled with use of the temperature adjustment means. The second pressure is higher than the first pressure and the second pressure is higher than or equal to an atmospheric pressure.

公开(公告)号：US12139446B2

公开(公告)日：2024-11-12

申请号：US17213709

申请日：2021-03-26

Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.

Inventor： Satoshi Seo ,  Nobuharu Ohsawa ,  Tomohiro Kubota ,  Takeyoshi Watabe ,  Airi Ueda ,  Yasushi Kitano ,  Takao Tosu

IPC: C07C211/56 ,  H10K50/15 ,  H10K50/17 ,  H10K85/60

Abstract: To provide a novel arylamine compound with a low refractive index. The provided arylamine compound includes at least one aromatic group. The aromatic group includes a first benzene ring, a second benzene ring, a third benzene ring, and at least three alkyl groups. The first benzene ring, the second benzene ring, and the third benzene ring are directly bonded in this order. The first benzene ring is bonded to nitrogen of amine. The first benzene ring may further include a substituted or unsubstituted phenyl group. The second benzene ring or the third benzene ring may further include an alkylated phenyl group. Each of first positions and third positions of two or more of the first to third benzene rings is independently bonded to another benzene ring, a benzene ring of the alkylated phenyl group, any of the at least three alkyl groups, or the nitrogen of the amine.

公开(公告)号：US09985221B2

公开(公告)日：2018-05-29

申请号：US14807426

申请日：2015-07-23

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Satoshi Seo ,  Takao Hamada ,  Tatsuyoshi Takahashi ,  Yasushi Kitano ,  Hiroki Suzuki ,  Hideko Inoue

IPC: H01L51/50 ,  H01L51/00 ,  C07D403/14

CPC classification number: H01L51/0072 ,  C07D403/14 ,  H01L51/006 ,  H01L51/0061 ,  H01L51/0085 ,  Y02P20/582

Abstract: To provide a light-emitting element with an improved reliability, a light-emitting element with a high current efficiency (or a high quantum efficiency), and a novel dibenzo[f,h]quinoxaline derivative that is favorably used in a light-emitting element which is one embodiment of the present invention. A light-emitting element includes an EL layer between an anode and a cathode. The EL layer includes a light-emitting layer; the light-emitting layer contains a first organic compound having an electron-transport property and a hole-transport property, a second organic compound having a hole-transport property, and a light-emitting substance; the combination of the first organic compound and the second organic compound forms an exciplex; the HOMO level of the first organic compound is lower than the HOMO level of the second organic compound; and a difference between the HOMO level of the first organic compound and the HOMO level of the second organic compound is less than or equal to 0.4 eV.

公开(公告)号：US09960368B2

公开(公告)日：2018-05-01

申请号：US15428634

申请日：2017-02-09

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hiroshi Kadoma ,  Yasushi Kitano ,  Satoko Shitagaki ,  Nobuharu Ohsawa ,  Satoshi Seo

IPC: H01L51/00 ,  C07D409/10 ,  C09K11/06 ,  C09K11/02 ,  H01L51/52 ,  H01L51/50

CPC classification number: H01L51/0072 ,  C07D403/10 ,  C07D405/10 ,  C07D409/10 ,  C09K11/025 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1014 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/185 ,  H01L51/0052 ,  H01L51/0056 ,  H01L51/0058 ,  H01L51/0073 ,  H01L51/0074 ,  H01L51/0085 ,  H01L51/5012 ,  H01L51/5016 ,  H01L51/5056 ,  H01L51/5072 ,  H01L51/508 ,  H01L51/5206 ,  H01L51/5221 ,  H05B33/14

Abstract: Provided is a novel heterocyclic compound which can be used for a light-emitting element, as a host material of a light-emitting layer in which a light-emitting substance is dispersed. A heterocyclic compound represented by a general formula (G1) is provided. In the formula, A represents any of a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted carbazolyl group, R11 to R19 separately represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and Ar represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms.

公开(公告)号：US09570690B2

公开(公告)日：2017-02-14

申请号：US14734067

申请日：2015-06-09

Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.

Inventor： Hiroshi Kadoma ,  Yasushi Kitano ,  Satoko Shitagaki ,  Nobuharu Ohsawa ,  Satoshi Seo

IPC: H01L51/00 ,  C07D403/10 ,  C07D405/10 ,  C07D409/10 ,  C09K11/06 ,  H05B33/14 ,  H01L51/50

CPC classification number: H01L51/0072 ,  C07D403/10 ,  C07D405/10 ,  C07D409/10 ,  C09K11/025 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1014 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/185 ,  H01L51/0052 ,  H01L51/0056 ,  H01L51/0058 ,  H01L51/0073 ,  H01L51/0074 ,  H01L51/0085 ,  H01L51/5012 ,  H01L51/5016 ,  H01L51/5056 ,  H01L51/5072 ,  H01L51/508 ,  H01L51/5206 ,  H01L51/5221 ,  H05B33/14

Abstract: Provided is a novel heterocyclic compound which can be used for a light-emitting element, as a host material of a light-emitting layer in which a light-emitting substance is dispersed. A heterocyclic compound represented by a general formula (G1) is provided. In the formula, A represents any of a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted carbazolyl group, R11 to R19 separately represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and Ar represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms.

Abstract translation: 提供可以用作发光元件的新颖的杂环化合物作为分散有发光物质的发光层的主体材料。 提供由通式（G1）表示的杂环化合物。 式中，A表示取代或未取代的二苯并噻吩基，取代或未取代的二苯并呋喃基，取代或未取代的咔唑基，R11〜R19分别表示氢，碳原子数为1〜4的烷基， 取代或未取代的碳原子数6〜13的芳基，Ar表示取代或未取代的碳原子数6〜13的亚芳基。

公开(公告)号：US09368732B2

公开(公告)日：2016-06-14

申请号：US14068319

申请日：2013-10-31

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Yasushi Kitano ,  Hiroshi Kadoma ,  Satoko Shitagaki ,  Satoshi Seo ,  Hiromi Seo ,  Tatsuyoshi Takahashi

IPC: H01L51/00 ,  C07D405/10 ,  C07D209/86 ,  C09K11/06

CPC classification number: H01L51/0072 ,  C07D209/86 ,  C07D405/10 ,  C09K11/06 ,  C09K2211/1416 ,  C09K2211/1425 ,  C09K2211/145 ,  C09K2211/1458 ,  H01L51/0073

Abstract: To provide a novel heterocyclic compound capable of being used as a host material in which a light-emitting substance is dispersed. To provide a light-emitting element having a long lifetime. A heterocyclic compound in which a dibenzo[f,h]quinoxalinyl group and a benzo[b]naphtho[1,2-d]furanyl group are bonded through an arylene group having 6 to 13 carbon atoms. The dibenzo[f,h]quinoxalinyl group, the benzo[b]naphtho[1,2-d]furanyl group, and the arylene group separately are unsubstituted or have, as a substituent, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 13 carbon atoms.

Abstract translation: 提供能够用作其中分散有发光物质的主体材料的新型杂环化合物。 提供寿命长的发光元件。 其中二苯并[f，h]喹喔啉基和苯并[b]萘并[1,2-d]呋喃基通过具有6至13个碳原子的亚芳基键合的杂环化合物。 二苯并[f，h]喹喔啉基，苯并[b]萘并[1,2-d]呋喃基和亚芳基分别是未取代的或具有取代基的具有1至4个碳原子的烷基或 具有6至13个碳原子的芳基。