公开(公告)号：US08829202B2

公开(公告)日：2014-09-09

申请号：US14237103

申请日：2012-08-03

申请人： Yoshinori Ikeda ,  Azusa Kohno ,  Takashi Shiro ,  Kazuo Takimiya

发明人： Yoshinori Ikeda ,  Azusa Kohno ,  Takashi Shiro ,  Kazuo Takimiya

IPC分类号： C07D495/14 ,  C07D495/18 ,  C07D495/04 ,  C07F7/08

CPC分类号： C07D495/04 ,  C07D495/18 ,  C07F7/0812 ,  H01L51/0036 ,  H01L51/0074 ,  H01L51/0094 ,  H01L51/0558

摘要： Provided is a condensed polycyclic aromatic compound that can be used as a precursor for synthesizing a condensed polycyclic aromatic compound having relatively high solubility. Also provided is a method for synthesizing and using such a novel condensed polycyclic aromatic compound. The condensed polycyclic aromatic compound is represented by formula (II): (II) (where X1 and X2 are each independently selected from the group consisting of a hydrogen atom, halogen atom, alkyl group, and the like, but at least one of X1 and X2 is a halogen atom; B is a condensed ring having at least one benzene ring moiety; each Y is independently selected from chalcogens; and A1 through A4 are each independently selected from the group consisting of hydrogen atoms, halogen atoms, alkyl groups, and the like and two adjacent atoms or groups can bond together to form an aromatic group).

摘要翻译： 提供可以用作合成具有较高溶解度的缩合多环芳族化合物的前体的缩合多环芳族化合物。 还提供了合成和使用这种新型缩合多环芳族化合物的方法。 缩合多环芳香族化合物由式（II）表示：（II）（其中X1和X2各自独立地选自氢原子，卤素原子，烷基等，但是X1中的至少一个 X2是卤素原子; B是具有至少一个苯环部分的稠环;每个Y独立地选自硫属元素;而A1至A4各自独立地选自氢原子，卤素原子，烷基， 等等和两个相邻的原子或基团可以键合在一起形成芳族基团）。

公开(公告)号：US09056871B2

公开(公告)日：2015-06-16

申请号：US13392996

申请日：2010-08-24

申请人： Yoshinori Ikeda ,  Takashi Shiro ,  Kazuo Takimiya

发明人： Yoshinori Ikeda ,  Takashi Shiro ,  Kazuo Takimiya

IPC分类号： C07D495/04 ,  C07D495/22 ,  C07D495/08 ,  C07D495/18 ,  C07D513/18 ,  H01L51/00 ,  H01L51/05

CPC分类号： C07D495/04 ,  C07D495/08 ,  C07D495/18 ,  C07D495/22 ,  C07D513/18 ,  H01L51/0053 ,  H01L51/0074 ,  H01L51/0545

摘要： Provided are a novel adduct compound and a novel α-diketone compound, from which organic semiconductor layers consisting of a fused polycyclic aromatic compound can be formed by a solution method, said solution method being generally easier than a deposition method. Also provided are a method for the purification of the adduct compound, and a solution for the formation of organic semiconductor film, which contains the adduct compound. The adduct compound has a structure wherein a compound having a double bond is added in an eliminable state to a fused polycyclic aromatic compound of general formula (I): Ar1Ar2Ar3 (I), while the α-diketone compound has a structure wherein a compound having a double bond is added in an eliminable state to a fused polycyclic aromatic compound. The fused polycyclic aromatic compound is dinaphthothienothiophene or the like, while the compound having a double bond is hexachlorocyclopentadiene or the like. In general formula (I), Ar1, Ar2 and Ar3 are each as defined in the description.

摘要翻译： 提供了一种新颖的加合物化合物和新的α-二酮化合物，通过溶液法可以形成由稠合多环芳族化合物组成的有机半导体层，所述溶液方法通常比沉积方法容易。 还提供了用于纯化加合物的方法和含有加合物化合物的用于形成有机半导体膜的溶液。 加成化合物具有这样的结构，其中具有双键的化合物以可消除的状态加入到通式（I）的稠合多环芳族化合物：Ar 1 Ar 2 Ar 3（I）中，而α-二酮化合物具有其中具有 在可消除状态下向稠合多环芳香族化合物添加双键。 稠合多环芳族化合物是二萘并噻吩噻吩等，而具有双键的化合物是六氯环戊二烯等。 在通式（I）中，Ar 1，Ar 2和Ar 3各自如说明书中所定义。

公开(公告)号：US20140187792A1

公开(公告)日：2014-07-03

申请号：US14237103

申请日：2012-08-03

申请人： Yoshinori Ikeda ,  Azusa Kohno ,  Takashi Shiro ,  Kazuo Takimiya

发明人： Yoshinori Ikeda ,  Azusa Kohno ,  Takashi Shiro ,  Kazuo Takimiya

IPC分类号： C07D495/04 ,  C07D495/18 ,  C07F7/08

CPC分类号： C07D495/04 ,  C07D495/18 ,  C07F7/0812 ,  H01L51/0036 ,  H01L51/0074 ,  H01L51/0094 ,  H01L51/0558

摘要： Provided is a condensed polycyclic aromatic compound that can be used as a precursor for synthesizing a condensed polycyclic aromatic compound having relatively high solubility. Also provided is a method for synthesizing and using such a novel condensed polycyclic aromatic compound. The condensed polycyclic aromatic compound is represented by formula (II): (II) (where X1 and X2 are each independently selected from the group consisting of a hydrogen atom, halogen atom, alkyl group, and the like, but at least one of X1 and X2 is a halogen atom; B is a condensed ring having at least one benzene ring moiety; each Y is independently selected from chalcogens; and A1 through A4 are each independently selected from the group consisting of hydrogen atoms, halogen atoms, alkyl groups, and the like and two adjacent atoms or groups can bond together to form an aromatic group.)

摘要翻译： 提供可以用作合成具有较高溶解度的缩合多环芳族化合物的前体的缩合多环芳族化合物。 还提供了合成和使用这种新型缩合多环芳族化合物的方法。 缩合多环芳香族化合物由式（II）表示：（II）（其中X1和X2各自独立地选自氢原子，卤素原子，烷基等，但是X1中的至少一个 X2是卤素原子; B是具有至少一个苯环部分的稠环;每个Y独立地选自硫属元素;而A1至A4各自独立地选自氢原子，卤素原子，烷基， 等等和两个相邻的原子或基团可以键合在一起形成芳族基团。）

公开(公告)号：US20120211731A1

公开(公告)日：2012-08-23

申请号：US13392996

申请日：2010-08-24

申请人： Yoshinori Ikeda ,  Takashi Shiro ,  Kazuo Takimiya

发明人： Yoshinori Ikeda ,  Takashi Shiro ,  Kazuo Takimiya

IPC分类号： H01L51/54 ,  C07D495/14 ,  B29C71/04 ,  H01B1/12 ,  B05D5/12 ,  C07D495/04 ,  C07D209/58

CPC分类号： C07D495/04 ,  C07D495/08 ,  C07D495/18 ,  C07D495/22 ,  C07D513/18 ,  H01L51/0053 ,  H01L51/0074 ,  H01L51/0545

摘要： Provided are a novel adduct compound and a novel α-diketone compound, from which organic semiconductor layers consisting of a fused polycyclic aromatic compound can be formed by a solution method, said solution method being generally easier than a deposition method. Also provided are a method for the purification of the adduct compound, and a solution for the formation of organic semiconductor film, which contains the adduct compound. The adduct compound has a structure wherein a compound having a double bond is added in an eliminable state to a fused polycyclic aromatic compound of general formula (I): Ar1Ar2Ar3 (I), while the α-diketone compound has a structure wherein a compound having a double bond is added in an eliminable state to a fused polycyclic aromatic compound. The fused polycyclic aromatic compound is dinaphthothienothiophene or the like, while the compound having a double bond is hexachlorocyclopentadiene or the like. In general formula (I), Ar1, Ar2 and Ar3 are each as defined in the description.

摘要翻译： 提供了一种新颖的加合物化合物和新的α-二酮化合物，通过溶液法可以形成由稠合多环芳族化合物组成的有机半导体层，所述溶液方法通常比沉积方法容易。 还提供了用于纯化加合物的方法和含有加合物化合物的用于形成有机半导体膜的溶液。 加成化合物具有这样的结构，其中具有双键的化合物以可消除的状态加入到通式（I）的稠合多环芳族化合物：Ar 1 Ar 2 Ar 3（I）中，而α-二酮化合物具有其中具有 在可消除状态下向稠合多环芳香族化合物添加双键。 稠合多环芳族化合物是二萘并噻吩噻吩等，而具有双键的化合物是六氯环戊二烯等。 在通式（I）中，Ar 1，Ar 2和Ar 3各自如说明书中所定义。

公开(公告)号：US20140163188A1

公开(公告)日：2014-06-12

申请号：US14234572

申请日：2012-07-25

申请人： Itaru Osaka ,  Kazuo Takimiya

发明人： Itaru Osaka ,  Kazuo Takimiya

IPC分类号： H01L51/00

CPC分类号： H01L51/0036 ,  C08G61/123 ,  C08G61/126 ,  C08G2261/124 ,  C08G2261/1412 ,  C08G2261/3223 ,  C08G2261/3243 ,  C08G2261/3246 ,  C08G2261/364 ,  C08G2261/414 ,  C08G2261/51 ,  C08G2261/91 ,  C08G2261/92 ,  H01L51/0043 ,  H01L51/0558 ,  H01L51/4253

摘要： Provided is an organic semiconductor material with good crystallinity and an excellent carrier mobility. The organic semiconductor material comprises a backbone represented by formula 1. In formula 1, R1 is hydrogen, an alkyl group, an alkylcarbonyl group, an alkoxy group, or an alkoxycarbonyl group, m is an integer of 1 or more, Ar is a monocyclic or condensed polycyclic heteroaromatic ring optionally comprising a substituent, and when a plurality of heteroaromatic rings are linked, the same or different heteroaromatic rings are optionally linked.

摘要翻译： 提供具有良好的结晶度和优异的载流子迁移率的有机半导体材料。 有机半导体材料包括由式1表示的主链。在式1中，R 1是氢，烷基，烷基羰基，烷氧基或烷氧基羰基，m是1或更大的整数，Ar是单环 或任选地包含取代基的稠合多环杂芳环，并且当多个杂芳环连接时，相同或不同的杂芳环任选地连接。

公开(公告)号：US20120116037A1

公开(公告)日：2012-05-10

申请号：US13375724

申请日：2010-05-11

申请人： Kazuo Takimiya ,  Kenji Kohiro ,  Hiroki Terai

发明人： Kazuo Takimiya ,  Kenji Kohiro ,  Hiroki Terai

IPC分类号： C08F234/04

CPC分类号： H01L51/0035 ,  C08G61/126 ,  C08G2261/124 ,  C08G2261/3223 ,  C08G2261/3243 ,  C08G2261/92 ,  H01L51/0036 ,  H01L51/0558

摘要： An organic thin-film transistor of the invention comprises an organic semiconductor layer that contains a polymer compound having a repeating unit represented by the following formula (1) and/or a repeating unit represented by the following formula (2), and a repeating unit represented by the following formula (3).

摘要翻译： 本发明的有机薄膜晶体管包含含有具有下述式（1）表示的重复单元的高分子化合物和/或下述式（2）表示的重复单元的有机半导体层，以及重复单元 由下式（3）表示。

公开(公告)号：US20110204295A1

公开(公告)日：2011-08-25

申请号：US13126771

申请日：2009-11-20

申请人： Hirokazu Kuwabara ,  Masaaki Ikeda ,  Kazuo Takimiya

发明人： Hirokazu Kuwabara ,  Masaaki Ikeda ,  Kazuo Takimiya

IPC分类号： C09K19/34 ,  H01B1/12 ,  C07D495/14 ,  C07D209/86

CPC分类号： C09K19/3491 ,  C07D495/14 ,  C07D517/14 ,  C09B57/00 ,  C09B57/008 ,  C09K11/06 ,  C09K19/40 ,  C09K2211/1011 ,  C09K2211/1014 ,  C09K2211/1029 ,  C09K2211/1092 ,  C09K2211/1096 ,  G02F1/133634 ,  H01L51/0059 ,  H01L51/006 ,  H01L51/0071 ,  H01L51/0072 ,  H01L51/0074 ,  H01L51/0541 ,  H01L51/0545 ,  H01L51/5048 ,  H05B33/14 ,  Y02E10/549

摘要： Disclosed are a heterocyclic compound characterized by being represented by formula (1), and a composition of the compound. Also disclosed is an organic electronic device using the compound. (In formula (1), X1, X2 and X3 each independently represents a sulfur atom or a selenium atom; and R1-R6 each independently represents an aromatic hydrocarbon group, an aliphatic hydrocarbon group, a halogen atom, a hydroxyl group, an alkoxyl group, a mercapto group, an alkylthio group, a boronic acid group, a nitro group, a substituted amino group, an amide group, an acyl group, a carboxyl group, an acyloxy group, a cyano group, a sulfo group, a sulfamoyl group, an alkylsulfamoyl group, a carbamoyl group, an alkylcarbamoyl group or a hydrogen atom, provided that all the R1-R6 are not hydrogen atoms at the same time.) The compound represented by formula (1) is suitable for use in an organic electronic device such as an organic EL element, an organic transistor element and a liquid crystal element.

摘要翻译： 公开了以式（1）表示的杂环化合物和化合物的组成。 还公开了使用该化合物的有机电子器件。 （式（1）中，X1，X2和X3各自独立地表示硫原子或硒原子; R1-R6分别独立地表示芳香族烃基，脂肪族烃基，卤素原子，羟基，烷氧基 基团，巯基，烷硫基，硼酸基，硝基，取代氨基，酰胺基，酰基，羧基，酰氧基，氰基，磺基，氨磺酰基 基团，烷基氨磺酰基，氨基甲酰基，烷基氨基甲酰基或氢原子，条件是所有的R 1 -R 6不同时为氢原子。）式（1）表示的化合物适用于有机 电子器件如有机EL元件，有机晶体管元件和液晶元件。

公开(公告)号：US20100137617A1

公开(公告)日：2010-06-03

申请号：US12451537

申请日：2008-05-13

申请人： Hirokazu Kuwabara ,  Masaaki Ikeda ,  Kazuo Takimiya

发明人： Hirokazu Kuwabara ,  Masaaki Ikeda ,  Kazuo Takimiya

IPC分类号： C07D495/04 ,  C07D345/00

CPC分类号： C07D495/04 ,  C07D495/22 ,  C07D517/04

摘要： Disclosed is a method for producing an aromatic compound represented by the general formula (2) below, which is characterized in that a compound represented by the general formula (1) below is reacted with a sulfur compound (at least one member selected from the group consisting of sulfur, hydrogen sulfide, metal hydrosulfides and metal sulfides) or a selenium compound. (In the formula (1), R1 represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an ester group, an optionally substituted alkyl group having 1-18 carbon atoms or the like; R2 represents a halogen atom; R3 represents a hydrogen atom, C≡C—R1 or R2; and n represents an integer of 0-4. When n is not less than 2, R3's may be the same as or different from each other.) (In the formula (2), R1, R3 and n are as defined in the formula (1); and X represents a sulfur atom or a selenium atom.)

摘要翻译： 公开了下述通式（2）表示的芳香族化合物的制造方法，其特征在于，将下述通式（1）表示的化合物与硫化合物（选自下述的至少一种 由硫，硫化氢，金属氢硫化物和金属硫化物组成）或硒化合物。 （式（1）中，R 1表示氢原子，卤素原子，羟基，氰基，硝基，酯基，可具有取代基的碳原子数为1〜18的烷基等; R 2 表示卤素原子; R3表示氢原子，C≡C-R1或R2; n表示0-4的整数，当n不小于2时，R 3可以相同或不同） （式（2）中，R 1，R 3，n如式（1）所定义，X表示硫原子或硒原子。

公开(公告)号：US09073938B2

公开(公告)日：2015-07-07

申请号：US12451537

申请日：2008-05-13

申请人： Hirokazu Kuwabara ,  Masaaki Ikeda ,  Kazuo Takimiya

发明人： Hirokazu Kuwabara ,  Masaaki Ikeda ,  Kazuo Takimiya

IPC分类号： C07D495/04 ,  C07D495/22 ,  C07D517/04

CPC分类号： C07D495/04 ,  C07D495/22 ,  C07D517/04

摘要： Disclosed is a method for producing an aromatic compound represented by the general formula (2) below, which is characterized in that a compound represented by the general formula (1) below is reacted with a sulfur compound (at least one member selected from the group consisting of sulfur, hydrogen sulfide, metal hydrosulfides and metal sulfides) or a selenium compound. (In the formula (1), R1 represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an ester group, an optionally substituted alkyl group having 1-18 carbon atoms or the like; R2 represents a halogen atom; R3 represents a hydrogen atom, C≡C—R1 or R2; and n represents an integer of 0-4. When n is not less than 2, R3's may be the same as or different from each other.) (In the formula (2), R1, R3 and n are as defined in the formula (1); and X represents a sulfur atom or a selenium atom.)

摘要翻译： 公开了下述通式（2）表示的芳香族化合物的制造方法，其特征在于，将下述通式（1）表示的化合物与硫化合物（选自下述的至少一种 由硫，硫化氢，金属氢硫化物和金属硫化物组成）或硒化合物。 （式（1）中，R 1表示氢原子，卤素原子，羟基，氰基，硝基，酯基，可具有取代基的碳原子数为1〜18的烷基等; R 2 表示卤素原子; R3表示氢原子，C≡C-R1或R2; n表示0-4的整数，当n不小于2时，R 3可以相同或不同） （式（2）中，R 1，R 3，n如式（1）所定义，X表示硫原子或硒原子。

公开(公告)号：US09018630B2

公开(公告)日：2015-04-28

申请号：US14000440

申请日：2012-02-24

申请人： Kazuo Takimiya ,  Kazuki Niimi ,  Hirokazu Kuwabara ,  Yuichi Sadamitsu ,  Eisei Kanoh

发明人： Kazuo Takimiya ,  Kazuki Niimi ,  Hirokazu Kuwabara ,  Yuichi Sadamitsu ,  Eisei Kanoh

IPC分类号： H01L51/05 ,  H01L51/40 ,  C07D495/04 ,  H01L51/00 ,  C07C319/20 ,  C09K11/06

CPC分类号： H01L51/0074 ,  C07C319/20 ,  C07D495/04 ,  C09B57/00 ,  C09K11/06 ,  C09K2211/1011 ,  C09K2211/1092 ,  H01L51/0558 ,  C07C321/28

摘要： Provided are a novel heterocyclic compound represented by formula (1), and a field-effect transistor having a semiconductor layer comprising the aforementioned compound. Also provided is a method for producing an intermediate enabling the production of the aforementioned novel heterocyclic compound. (In the formula, R1 and R2 represent a hydrogen atom, a C2-16 alkyl group or an aryl group. However, when R1 each independently represents a C2-16 alkyl group or an aryl group, R2 represents a hydrogen atom or each independently represents an aryl group; and when R1 represents a hydrogen atom, R2 each independently represents an aryl group.)

摘要翻译： 提供由式（1）表示的新型杂环化合物和具有包含上述化合物的半导体层的场效应晶体管。 还提供了一种能够制备上述新型杂环化合物的中间体的制备方法。 （式中，R 1，R 2表示氢原子，C 16-16烷基或芳基，但R 1各自独立地表示C 2-6烷基或芳基时，R 2表示氢原子， 表示芳基;当R 1表示氢原子时，R 2各自独立地表示芳基。