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    • 5. 发明授权
    • Condensation compound between fluorinated cyclopentane ring and aromatic ring, and process for producing the same
    • 氟化环戊烷环和芳环之间的缩合化合物及其制备方法
    • US08008336B2
    • 2011-08-30
    • US11885913
    • 2006-03-02
    • Yutaka IeYoshio Aso
    • Yutaka IeYoshio Aso
    • A61K31/409C07D495/22
    • C07D495/20C07D333/78H01L51/0036
    • A condensation compound of a fluorinated cyclopentane ring and an aromatic ring, which is useful, for example, for electronic materials, and a process for producing the same are provided. For instance, according to Scheme 1 below, a compound (68) containing a condensed structure formed of a hexafluorocyclopentane ring and an aromatic ring is synthesized. The aromatic ring is not limited to a thiophene ring but can be any ring and any substituent can be used. Thus a compound containing a condensed ring structure formed of a hexafluorocyclopentane ring and an aromatic ring, particularly, for instance, a thiophene ring, which was impossible to produce conventionally, can be produced easily with high yield. The compound of the present invention is particularly suitable to be applied to, for example, electronic materials or semiconductors. When it is polymerized and thereby the π-electronic conjugation is extended, it also is expected to be applied to, for example, n-type organic semiconductors and molecular wires that are indispensable for developing molecular electronics elements.
    • 提供氟化环戊烷环和芳环的缩合化合物,其可用于例如电子材料,以及其制备方法。 例如,根据下述方案1,合成含有由六氟环戊烷环和芳香环形成的稠合结构的化合物(68)。 芳环不限于噻吩环,而是可以是任何环,并且可以使用任何取代基。 因此,可以容易地以高产率制备含有由六氟环戊烷环和芳环形成的稠环结构的化合物,特别是例如噻吩环,这是不可能制备的。 本发明的化合物特别适用于例如电子材料或半导体。 当其被聚合并由此延长了电子共轭时,也可以应用于例如用于开发分子电子元件不可或缺的n型有机半导体和分子线。
    • 7. 发明申请
    • CONJUGATED COMPOUND, NITROGENATED CONDENSED-RING COMPOUND, NITROGENATED CONDENSED-RING POLYMER, ORGANIC THIN FILM, AND ORGANIC THIN FILM ELEMENT
    • 连结化合物,氮化聚合环化合物,氮化聚合物聚合物,有机薄膜和有机薄膜元件
    • US20100301314A1
    • 2010-12-02
    • US12745481
    • 2008-11-27
    • Yoshio AsoYutaka IeMakoto OkabeMasashi NitaniMasato Ueda
    • Yoshio AsoYutaka IeMakoto OkabeMasashi NitaniMasato Ueda
    • H01L51/30C07D513/04C07D513/20C07D411/14
    • H01L51/0069C07D277/60C07D333/22C07D333/78C07D409/14C07D417/14C09B3/78C09B57/00C09B57/001H01L51/0036H01L51/0558Y02E10/549
    • According to the first invention group there are provided conjugated compounds having two or more groups represented by the following formula (I) or the following formula (II): wherein one of Ar and Ar′ represents a C6 or greater divalent aromatic hydrocarbon group and the other represents a C4 or greater divalent heterocyclic group, wherein the groups each may have a substituent, with the proviso that the groups as a whole contain no fluorine atoms, R1 and R2 each independently represent a hydrogen atom, a halogen atom or a monovalent group, and Ar″ represents a trivalent aromatic hydrocarbon or trivalent heterocyclic group; when the conjugated compound has two or more groups represented by formula (I), the portion excluding these groups contain no fluorine atoms.According to the second group of the present invention there are provided nitrogen-containing fused-ring compounds represented by the following formula (α-I): in formula (α-I), R21 and R22 each independently represent a hydrogen atom, a halogen atom or an optionally substituted monovalent group, and Z21 and Z22 each independently represent any one of the groups represented by the following formulas (α-i)-(α-ix); wherein R23, R24, R25 and R26 each independently represent a hydrogen atom, a halogen atom or a monovalent group, and R23 and R24 may bond together to form a ring, the left side and the right side of the group represented by formula (α-viii) may be interchanged.
    • 根据第一发明组,提供具有两个以上由下式(I)或下式(II)表示的基团的共轭化合物:其中Ar和Ar'中的一个表示C6以上的二价芳香族烃基, 其它表示C4以上的二价杂环基,其中各基团可以具有取代基,条件是基团整体上不含氟原子,R 1和R 2各自独立地表示氢原子,卤素原子或一价基团 ,Ar“表示三价芳香族烃或三价杂环基; 当共轭化合物具有两个以上由式(I)表示的基团时,不包括这些基团的部分不含氟原子。 根据本发明的第二组,提供由下式(α-I)表示的含氮稠环化合物:在式(α-I)中,R 21和R 22各自独立地表示氢原子,卤素 原子或任选取代的一价基团,Z 21和Z 22各自独立地表示由下式(α-i) - (α-ix)表示的基团中的任一个。 其中R 23,R 24,R 25和R 26各自独立地表示氢原子,卤素原子或一价基团,R 23和R 24可以键合在一起形成环,式(α)表示的基团的左侧和右侧 -viii)可以互换。
    • 10. 发明授权
    • Conjugated compound, nitrogenated condensed-ring compound, nitrogenated condensed-ring polymer, organic thin film, and organic thin film element
    • 共轭化合物,氮化稠环化合物,氮化缩合环聚合物,有机薄膜和有机薄膜元件
    • US08378338B2
    • 2013-02-19
    • US12745481
    • 2008-11-27
    • Yoshio AsoYutaka IeMakoto OkabeMasashi NitaniMasato Ueda
    • Yoshio AsoYutaka IeMakoto OkabeMasashi NitaniMasato Ueda
    • H01L29/08
    • H01L51/0069C07D277/60C07D333/22C07D333/78C07D409/14C07D417/14C09B3/78C09B57/00C09B57/001H01L51/0036H01L51/0558Y02E10/549
    • According to the first invention group there are provided conjugated compounds having two or more groups represented by the following formula (I) or the following formula (II): wherein one of Ar and Ar′ represents a C6 or greater divalent aromatic hydrocarbon group and the other represents a C4 or greater divalent heterocyclic group, wherein the groups each may have a substituent, with the proviso that the groups as a whole contain no fluorine atoms, R1 and R2 each independently represent a hydrogen atom, a halogen atom or a monovalent group, and Ar″ represents a trivalent aromatic hydrocarbon or trivalent heterocyclic group; when the conjugated compound has two or more groups represented by formula (I), the portion excluding these groups contain no fluorine atoms. According to the second group of the present invention there are provided nitrogen-containing fused-ring compounds represented by the following formula (α-I): in formula (α-I), R21 and R22 each independently represent a hydrogen atom, a halogen atom or an optionally substituted monovalent group, and Z21 and Z22 each independently represent any one of the groups represented by the following formulas (α-i)-(α-ix); wherein R23, R24, R25 and R26 each independently represent a hydrogen atom, a halogen atom or a monovalent group, and R23 and R24 may bond together to form a ring, the left side and the right side of the group represented by formula (α-viii) may be interchanged.
    • 根据第一发明组,提供具有两个以上由下式(I)或下式(II)表示的基团的共轭化合物:其中Ar和Ar'中的一个表示C6以上的二价芳香族烃基, 其它表示C4以上的二价杂环基,其中各基团可以具有取代基,条件是基团整体上不含氟原子,R 1和R 2各自独立地表示氢原子,卤素原子或一价基团 ,Ar“表示三价芳香族烃或三价杂环基; 当共轭化合物具有两个以上由式(I)表示的基团时,不包括这些基团的部分不含氟原子。 根据本发明的第二组,提供由下式(α-I)表示的含氮稠环化合物:在式(α-I)中,R 21和R 22各自独立地表示氢原子,卤素 原子或任选取代的一价基团,Z 21和Z 22各自独立地表示由下式(α-i) - (α-ix)表示的基团中的任一个。 其中R 23,R 24,R 25和R 26各自独立地表示氢原子,卤素原子或一价基团,R 23和R 24可以键合在一起形成环,式(α)表示的基团的左侧和右侧 -viii)可以互换。