公开(公告)号：US07935828B2

公开(公告)日：2011-05-03

申请号：US11445940

申请日：2006-06-02

申请人： Ken Tomino ,  Shigeru Sugawara ,  Hiroki Maeda ,  Masanao Matsuoka

发明人： Ken Tomino ,  Shigeru Sugawara ,  Hiroki Maeda ,  Masanao Matsuoka

IPC分类号： H01L21/00 ,  H01L51/30 ,  C07D513/04

CPC分类号： H01L51/0071 ,  C09K19/3491 ,  C09K19/3497 ,  H01L51/0076 ,  H01L51/0545 ,  H01L51/0558 ,  Y02E10/549

摘要： The present invention is directed to the provision of a novel liquid crystalline organic semiconductor material that is highly stable under an film forming environment and, at the same time, can easily form a film, for example, by coating. The liquid crystalline organic semiconductor material is represented by chemical formula 1 wherein R1 and R2 represent an identical alkyl group having 7 to 20 carbon atoms: There is also provided a liquid crystalline organic semiconductor material characterized by being represented by chemical formula 2 wherein R3 and R4 represent an identical alkyl group having 7 to 20 carbon atoms:

摘要翻译： 本发明涉及提供一种在成膜环境下高度稳定的新型液晶有机半导体材料，同时可以容易地通过涂布形成膜。 液晶有机半导体材料由化学式1表示，其中R 1和R 2表示相同的具有7至20个碳原子的烷基。还提供了以化学式2表示的液晶有机半导体材料，其中R3和R4 表示具有7至20个碳原子的相同的烷基：

公开(公告)号：US20070128763A1

公开(公告)日：2007-06-07

申请号：US11445939

申请日：2006-06-02

申请人： Ken Tomino ,  Shigeru Sugawara ,  Hiroki Maeda ,  Masanao Matsuoka

发明人： Ken Tomino ,  Shigeru Sugawara ,  Hiroki Maeda ,  Masanao Matsuoka

IPC分类号： H01L51/40

CPC分类号： H01L51/0007 ,  H01L51/0036 ,  H01L51/0076 ,  H01L51/0545 ,  H01L51/0558 ,  Y02E10/549

摘要： This invention is directed to the provision of a method for organic semiconductor layer formation that can easily form a uniform thin film, by coating, which has good charge mobility and a high level of alignment. The method for organic semiconductor layer formation is characterized by comprising the steps of: forming a coating film in a mixed liquid crystal state using a mixture, which can exhibit a thermotropic mixed liquid crystal phase, prepared by mixing an organic semiconductor material with a solvent; and either cooling the coating film to a temperature at which the coating film does not exhibit any mixed liquid crystal state, or removing the solvent while cooling the coating film, to form an organic semiconductor layer comprising a smectic liquid crystal phase or a crystal phase of the organic semiconductor material.

摘要翻译： 本发明涉及提供一种有机半导体层形成方法，其可以容易地形成具有良好的电荷迁移率和较高取向度的均匀的薄膜。 有机半导体层形成方法的特征在于包括以下步骤：使用可以显示通过将有机半导体材料与溶剂混合制备的热致混合液晶相的混合物形成混合液晶状态的涂膜; 并且将涂膜冷却至涂膜不显示任何混合液晶状态的温度，或者在冷却涂膜的同时除去溶剂，形成有机半导体层，该有机半导体层包括层间界面液晶相或晶相 有机半导体材料。

公开(公告)号：US20100224869A1

公开(公告)日：2010-09-09

申请号：US12782046

申请日：2010-05-18

申请人： Ken Tomino ,  Shigeru Sugawara ,  Hiroki Maeda ,  Masanao Matsuoka

发明人： Ken Tomino ,  Shigeru Sugawara ,  Hiroki Maeda ,  Masanao Matsuoka

IPC分类号： H01L51/10 ,  C07D409/14

CPC分类号： H01L51/0068 ,  H01L51/0541 ,  H01L51/0545 ,  Y02E10/549

摘要： The present invention is directed to the provision of a liquid crystalline organic semiconductor material, which is highly stable under a film forming environment and, at the same time, can easily form a film, for example, by coating. The liquid crystalline organic semiconductor material comprises: a thiophene skeleton comprising 3 to 6 thiophenes linearly connected to each other; and an identical alkyl group having 1 to 20 carbon atoms located on both sides of the thiophene skeleton, wherein acetylene skeletons each have been introduced into between the thiophene skeleton and the alkyl group, or acetylene skeletons have been introduced symmetrically into the thiophene skeleton.

摘要翻译： 本发明涉及提供一种在成膜环境下高度稳定的液晶有机半导体材料，同时可以容易地通过涂布形成膜。 液晶有机半导体材料包括：包含彼此线性连接的3至6个噻吩的噻吩骨架; 和位于噻吩骨架两侧的碳原子数为1〜20的相同的烷基，其中分别引入了噻吩骨架和烷基之间的乙炔骨架，或者将乙炔骨架对称引入到噻吩骨架中。

公开(公告)号：US20070128764A1

公开(公告)日：2007-06-07

申请号：US11445940

申请日：2006-06-02

申请人： Ken Tomino ,  Shigeru Sugawara ,  Hiroki Maeda ,  Masanao Matsuoka

发明人： Ken Tomino ,  Shigeru Sugawara ,  Hiroki Maeda ,  Masanao Matsuoka

IPC分类号： H01L29/08 ,  H01L51/40

CPC分类号： H01L51/0071 ,  C09K19/3491 ,  C09K19/3497 ,  H01L51/0076 ,  H01L51/0545 ,  H01L51/0558 ,  Y02E10/549

摘要： The present invention is directed to the provision of a novel liquid crystalline organic semiconductor material that is highly stable under an film forming environment and, at the same time, can easily form a film, for example, by coating. The liquid crystalline organic semiconductor material is represented by chemical formula 1 wherein R1 and R2 represent an identical alkyl group having 7 to 20 carbon atoms: There is also provided a liquid crystalline organic semiconductor material characterized by being represented by chemical formula 2 wherein R3 and R4 represent an identical alkyl group having 7 to 20 carbon atoms:

摘要翻译： 本发明涉及提供一种在成膜环境下高度稳定的新型液晶有机半导体材料，同时可以容易地通过涂布形成膜。 液晶有机半导体材料由化学式1表示，其中R 1和R 2表示相同的具有7至20个碳原子的烷基。还提供了以化学式2表示的液晶有机半导体材料，其中R3和R4 表示具有7至20个碳原子的相同的烷基：

公开(公告)号：US07408188B2

公开(公告)日：2008-08-05

申请号：US11449040

申请日：2006-06-07

申请人： Shigeru Sugawara ,  Hiroki Maeda ,  Ken Tomino ,  Masanao Matsuoka

发明人： Shigeru Sugawara ,  Hiroki Maeda ,  Ken Tomino ,  Masanao Matsuoka

IPC分类号： H01L51/30 ,  C07D333/10

CPC分类号： H01L51/0036 ,  C08G61/126 ,  C08G83/005 ,  H01L51/0545 ,  Y02E10/549

摘要： An organic semiconductor material characterized by having a structure represented by chemical formula 1, the planarity of a main chain A1-X-A2 being disintegrated by steric hindrance between B1 and X and steric hindrance between B2 and X, the organic semiconductor material having a number average molecular weight of about 2,000 to about 200,000: wherein A1, A2, B1, B2 and X each have a skeleton structure comprising L 6 π electron rings, M 8 π electron rings, N 10 π electron rings, O 12 π electron rings, P 14 π electron rings, Q 16 π electron rings, R 18 π electron rings, S 20 π electron rings, T 22 π electron rings, U 24 π electron rings, and V 26 π electron rings, wherein L, M, N, O, P, Q, R, S, T, U, and V are each an integer of 0 (zero) to 6 and L+M+N+O+P+Q+R+S+T+U+V=1 to 6; and B1 and B2 have an alkyl group.

摘要翻译： 特征在于具有由化学式1表示的结构的有机半导体材料，通过B1与X之间的空间位阻分解的主链A1-X-A2的平面性和B2与X之间的空间位阻，有机半导体材料具有数 平均分子量为约2,000至约200,000：其中A1，A2，B1，B2和X各自具有包括L 6π电子环，M 8π电子环，N 10π电子环，O 12π电子环的骨架结构， P 14π电子环，Q 16π电子环，R 18π电子环，S 20π电子环，T 22π电子环，U 24π电子环和V 26π电子环，其中L，M，N， O，P，Q，R，S，T，U和V各自为0（零）至6的整数，L + M + N + O + P + Q + R + S + T + U + V = 1至6; 而B1和B2具有烷基。

公开(公告)号：US20070045614A1

公开(公告)日：2007-03-01

申请号：US11449040

申请日：2006-06-07

申请人： Shigeru Sugawara ,  Hiroki Maeda ,  Ken Tomino ,  Masanao Matsuoka

发明人： Shigeru Sugawara ,  Hiroki Maeda ,  Ken Tomino ,  Masanao Matsuoka

IPC分类号： C08G75/32 ,  H01L51/00

CPC分类号： H01L51/0036 ,  C08G61/126 ,  C08G83/005 ,  H01L51/0545 ,  Y02E10/549

摘要： An organic semiconductor material characterized by having a structure represented by chemical formula 1, the planarity of a main chain A1-X-A2 being disintegrated by steric hindrance between B1 and X and steric hindrance between B2 and X, the organic semiconductor material having a number average molecular weight of about 2,000 to about 200,000: wherein A1, A2, B1, B2 and X each have a skeleton structure comprising L 6 π electron rings, M 8 π electron rings, N 10 π electron rings, O 12 π electron rings, P 14 π electron rings, Q 16 π electron rings, R 18 π electron rings, S 20 π electron rings, T 22 π electron rings, U 24 π electron rings, and V 26 π electron rings, wherein L, M, N, O, P, Q, R, S, T, U, and V are each an integer of 0 (zero) to 6 and L+M+N+O+P+Q+R+S+T+U+V=1 to 6; and B1 and B2 have an alkyl group.

摘要翻译： 特征在于具有由化学式1表示的结构的有机半导体材料，通过B1与X之间的空间位阻分解的主链A1-X-A2的平面度和B2与X之间的空间位阻，有机半导体材料具有数 平均分子量为约2,000至约200,000：其中A1，A2，B1，B2和X各自具有包含L 6π电子环，M 8π电子环，N 10π电子环，O 12π电子环的骨架结构， P 14π电子环，Q 16π电子环，R 18π电子环，S 20π电子环，T 22π电子环，U 24π电子环和V 26π电子环，其中L，M，N， O，P，Q，R，S，T，U和V各自为0（零）至6的整数，L + M + N + O + P + Q + R + S + T + U + V = 1至6; 而B1和B2具有烷基。

公开(公告)号：US20070045613A1

公开(公告)日：2007-03-01

申请号：US11445919

申请日：2006-06-02

申请人： Ken Tomino ,  Shigeru Sugawara ,  Hiroki Maeda ,  Masanao Matsuoka

发明人： Ken Tomino ,  Shigeru Sugawara ,  Hiroki Maeda ,  Masanao Matsuoka

IPC分类号： H01L29/08 ,  H01L35/24 ,  H01L51/00

CPC分类号： H01L51/0068 ,  H01L51/0541 ,  H01L51/0545 ,  Y02E10/549

摘要： The present invention is directed to the provision of a liquid crystalline organic semiconductor material, which is highly stable under a film forming environment and, at the same time, can easily form a film, for example, by coating. The liquid crystalline organic semiconductor material comprises: a thiophene skeleton comprising 3 to 6 thiophenes linearly connected to each other; and an identical alkyl group having 1 to 20 carbon atoms located on both sides of the thiophene skeleton, wherein acetylene skeletons each have been introduced into between the thiophene skeleton and the alkyl group, or acetylene skeletons have been introduced symmetrically into the thiophene skeleton.

摘要翻译： 本发明涉及提供一种在成膜环境下高度稳定的液晶有机半导体材料，同时可以容易地通过涂布形成膜。 液晶有机半导体材料包括：包含彼此线性连接的3至6个噻吩的噻吩骨架; 和位于噻吩骨架两侧的碳原子数为1〜20的相同的烷基，其中分别引入了噻吩骨架和烷基之间的乙炔骨架，或者将乙炔骨架对称引入到噻吩骨架中。

公开(公告)号：US08202759B2

公开(公告)日：2012-06-19

申请号：US12863538

申请日：2009-01-21

申请人： Ken Tomino ,  Masanao Matsuoka ,  Tomomi Suzuki ,  Hiroki Maeda

发明人： Ken Tomino ,  Masanao Matsuoka ,  Tomomi Suzuki ,  Hiroki Maeda

IPC分类号： H01L51/40

CPC分类号： H01L51/0013 ,  H01L51/003 ,  H01L51/0076 ,  H01L51/0545 ,  H01L51/0558

摘要： The present invention provides a manufacturing method of an organic semiconductor device comprising a step of transferring an organic semiconductor layer to a gate insulation layer by a thermal transfer at a liquid crystal phase transition temperature of a liquid crystalline organic semiconductor material, and the step uses: an organic semiconductor layer-transferring substrate comprising a parting substrate having parting properties, and the organic semiconductor layer formed on the parting substrate and containing the liquid crystalline organic semiconductor material; and a substrate for forming an organic semiconductor device comprising a substrate, a gate electrode formed on the substrate, and the gate insulation layer formed to cover the gate electrode and having alignment properties which are capable of aligning the liquid crystalline organic semiconductor material on a surface of the gate insulation layer.

摘要翻译： 本发明提供了一种有机半导体器件的制造方法，其包括通过在液晶有机半导体材料的液晶相变温度下的热转印将有机半导体层转印到栅极绝缘层的步骤，并且该步骤用途： 包括具有分离性质的分离基板的有机半导体层转移基板和形成在分型基板上并含有液晶有机半导体材料的有机半导体层; 以及用于形成有机半导体器件的衬底，包括衬底，形成在衬底上的栅极电极和形成为覆盖栅电极并具有能够使液晶有机半导体材料在表面上对准的取向性能的栅极绝缘层 的栅极绝缘层。

公开(公告)号：US20110053313A1

公开(公告)日：2011-03-03

申请号：US12863538

申请日：2009-01-21

申请人： Ken Tomino ,  Masanao Matsuoka ,  Tomomi Suzuki ,  Hiroki Maeda

发明人： Ken Tomino ,  Masanao Matsuoka ,  Tomomi Suzuki ,  Hiroki Maeda

IPC分类号： H01L51/10

CPC分类号： H01L51/0013 ,  H01L51/003 ,  H01L51/0076 ,  H01L51/0545 ,  H01L51/0558

摘要： The present invention provides a manufacturing method of an organic semiconductor device comprising a step of transferring an organic semiconductor layer to a gate insulation layer by a thermal transfer at a liquid crystal phase transition temperature of a liquid crystalline organic semiconductor material, and the step uses: an organic semiconductor layer-transferring substrate comprising a parting substrate having parting properties, and the organic semiconductor layer formed on the parting substrate and containing the liquid crystalline organic semiconductor material; and a substrate for forming an organic semiconductor device comprising a substrate, a gate electrode formed on the substrate, and the gate insulation layer formed to cover the gate electrode and having alignment properties which are capable of aligning the liquid crystalline organic semiconductor material on a surface of the gate insulation layer.

摘要翻译： 本发明提供了一种有机半导体器件的制造方法，其包括通过在液晶有机半导体材料的液晶相变温度下的热转印将有机半导体层转印到栅极绝缘层的步骤，并且该步骤用途： 包括具有分离性质的分离基板的有机半导体层转移基板和形成在分型基板上并含有液晶有机半导体材料的有机半导体层; 以及用于形成有机半导体器件的衬底，包括衬底，形成在衬底上的栅极电极和形成为覆盖栅电极并具有能够使液晶有机半导体材料在表面上对准的取向性能的栅极绝缘层 的栅极绝缘层。

公开(公告)号：US20060076554A1

公开(公告)日：2006-04-13

申请号：US11092238

申请日：2005-03-29

申请人： Hiroki Maeda ,  Ken Tomino ,  Shigeru Sugawara ,  Masahiro Funahashi ,  Junichi Hanna

发明人： Hiroki Maeda ,  Ken Tomino ,  Shigeru Sugawara ,  Masahiro Funahashi ,  Junichi Hanna

IPC分类号： H01L29/08

CPC分类号： H01L51/0068 ,  H01L51/0036 ,  H01L51/0076 ,  H01L51/0545 ,  Y02E10/549 ,  Y10T428/31504

摘要： The object is to provide an organic semiconductor material, enabling to exhibit liquid crystal phase at wide temperature range including at least ordinary temperature and to exhibit high charge carrier mobility, and an organic semiconductor structure and organic semiconductor device formed from the organic semiconductor material. To achieve the object, the present invention provides an organic semiconductor material comprising a quaterthiophene skeleton shown in a following chemical formula 1, wherein R1 in the chemical formula 1 is an alkyl group of C1 to C20 or a hydrogen, and R2 is an alkyl group of C1 to C20 or a hydrogen.

摘要翻译： 本发明的目的是提供一种有机半导体材料，其能够在至少包含常温的宽温度范围内显示出液晶相，并表现出高的载流子迁移率，以及由有机半导体材料形成的有机半导体结构和有机半导体器件。 为了达到上述目的，本发明提供一种有机半导体材料，其含有下述化学式1所示的四噻吩骨架，其中化学式1中的R1为C1〜C20的烷基或氢，R2为烷基 的C1至C20或氢。