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1. 发明公开

EP3372581A1 FULLERENE DERIVATIVE AND n-TYPE SEMICONDUCTOR MATERIAL 有权
公开(公告)号：EP3372581A1
公开(公告)日：2018-09-12
申请号：EP16853695.1
申请日：2016-10-06
申请人： Daikin Industries, Ltd. , Osaka University
发明人： NAGAI, Takabumi , ADACHI, Kenji , ASO, Yoshio , IE, Yutaka , KARAKAWA, Makoto
IPC分类号： C07D209/52 , H01L51/46
CPC分类号： C07D209/52 , C01B32/154 , H01L31/02167 , H01L51/0047 , H01L51/4253 , H01L51/441
摘要： An object of the present invention is to provide a novel fullerene derivative usable in n-type semiconductor materials for organic thin-film solar cells and the like. The object is achieved by a fullerene derivative represented by formula (1)

wherein R 1 represents aryl optionally substituted with at least one substituent, R 2 represents an organic group, R 3 represents an organic group, with the proviso that at least one of R 2 and R 3 is alkyl optionally substituted with at least one substituent or alkyl ether optionally substituted with at least one substituent, R 4 represents hydrogen or an organic group, and a ring A represents a fullerene ring.

2. 发明公开

EP2998293A1 FULLERENE DERIVATIVE AND N-TYPE SEMICONDUCTOR MATERIAL 审中-公开
标题翻译： FULLERENDERIVAT UND N-TYP-HALBLEITERMATERIAL
公开(公告)号：EP2998293A1
公开(公告)日：2016-03-23
申请号：EP14797515.5
申请日：2014-05-16
申请人： Daikin Industries, Ltd. , Osaka University
发明人： NAGAI, Takabumi , ADACHI, Kenji , ASO, Yoshio , IE, Yutaka , KARAKAWA, Makoto
IPC分类号： C07D209/70 , C07D409/04 , C07D417/04 , H01L51/05 , H01L51/30 , H01L51/46
CPC分类号： H01L51/0047 , C07D209/70 , C07D409/04 , C07D417/04 , H01L51/4253 , Y02E10/549
摘要： An object of the present invention is to provide a material that exhibits excellent properties as an n-type semiconductor, in particular as an n-type semiconductor for use in a photoelectric conversion element, such as organic thin-film solar cells. The present invention relates to a fullerene derivative represented by formula (1):

wherein
R 1a and R 1b are the same or different, and each represents a hydrogen atom or a fluorine atom;
R 1c and R 1d are the same or different, and each represents a hydrogen atom, a fluorine atom, alkyl, alkoxy, ester, or cyano;
R 2 represents (1) phenol optionally substituted with at least one substituent selected from the group consisting of fluorine, alkyl, alkoxy, ester, and cyano, or (2) a 5-membered heteroaryl group optionally substituted with 1 to 3 methyl groups; and
ring A represents a fullerene ring,
with the proviso that when R 1a , R 1b , R 1c , and R 1d are each a hydrogen atom, R 2 represents phenyl substituted with 1 or 2 fluorine atoms or a 5-membered heteroaryl group optionally substituted with 1 to 3 methyl groups.
摘要翻译：本发明的目的是提供一种作为n型半导体具有优异性能的材料，特别是作为用于诸如有机薄膜太阳能电池的光电转换元件中的n型半导体。本发明涉及由式（1）表示的富勒烯衍生物：其中R 1a和R 1b相同或不同，各自表示氢原子或氟原子; R 1c和R 1d相同或不同，各自表示氢原子，氟原子，烷基，烷氧基，酯或氰基; R 2表示（1）任选被至少一个选自氟，烷基，烷氧基，酯和氰基的取代基取代的苯酚，或（2）任选被1至3个甲基取代的5元杂芳基; 环A表示富勒烯环，条件是当R 1a，R 1b，R 1c和R 1d各自为氢原子时，R 2表示被1或2个氟原子取代的苯基或任选的5元杂芳基被1〜3个甲基取代。

3. 发明公开

EP2999018A1 FULLERENE DERIVATIVE AND N-TYPE SEMICONDUCTOR MATERIAL 有权转让
标题翻译： FULLERENE衍生和N型半导体材料
公开(公告)号：EP2999018A1
公开(公告)日：2016-03-23
申请号：EP14798196.3
申请日：2014-05-16
申请人： Daikin Industries, Ltd. , Osaka University
发明人： NAGAI, Takabumi , ADACHI, Kenji , ASO, Yoshio , IE, Yutaka , KARAKAWA, Makoto
IPC分类号： H01L51/46 , C07D209/58 , C08K3/04 , C08L65/00
CPC分类号： H01L51/0047 , C07D209/70 , C08G2261/124 , C08G2261/3142 , C08G2261/3223 , C08G2261/3243 , C08G2261/91 , C08K3/045 , H01L51/0036 , H01L51/0037 , H01L51/005 , H01L51/4253 , Y02E10/549 , C08K3/04 , C08L65/00
摘要： The object of the present invention is to provide a material having excellent performance as an n-type semiconductor material, in particular an n-type semiconductor for photoelectric conversion elements such as organic thin-film solar cells.
The present invention provides an n-type semiconductor consisting of a fullerene derivative having a purity of 99% or more as defined below, the fullerene derivative being represented by formula (1):

wherein ring A represents C 60 fullerene;
R 1 represents a hydrogen atom, alkyl optionally having at least one substituent, or aryl optionally having at least one substituent; and
Ar represents aryl optionally substituted with at least one alkyl group,
the purity being defined by the following equation: Purity % = 100 − D max %
wherein the D max (%) is the maximum value among the absolute value of the difference between an analysis value and a theoretical value obtained in elemental analysis of carbon, the absolute value of the difference between an analysis value and a theoretical value obtained in elemental analysis of hydrogen, and the absolute value of the difference between an analysis value and a theoretical value obtained in elemental analysis of nitrogen.
摘要翻译：本发明的目的是提供一种作为n型半导体材料，特别是用于诸如有机薄膜太阳能电池等光电转换元件的n型半导体的优异性能的材料。本发明提供由富勒烯衍生物构成的n型半导体，所述富勒烯衍生物具有99％以上的纯度，所述富勒烯衍生物由式（1）表示：其中环A表示C 60富勒烯; R 1表示氢原子，任选具有至少一个取代基的烷基或任选具有至少一个取代基的芳基; Ar表示任选被至少一个烷基取代的芳基，纯度由下式定义：纯度％= 100-Dmax％其中Dmax（％）是分析值之间的差值的绝对值中的最大值碳的元素分析中得到的理论值，氢的元素分析中得到的分析值与理论值之差的绝对值，以及元素分析中得到的分析值与理论值之差的绝对值氮分析。

4. 发明公开

EP2223918A1 CONJUGATED COMPOUND, NITROGENATED CONDENSED-RING COMPOUND, NITROGENATED CONDENSED-RING POLYMER, ORGANIC THIN FILM, AND ORGANIC THIN FILM ELEMENT 审中-公开
标题翻译：共轭连接，具有NITROGENIERTEM稠环连接，具有NITROGENIERTEM稠环聚合物，有机薄膜以及有机薄膜元件，具有
公开(公告)号：EP2223918A1
公开(公告)日：2010-09-01
申请号：EP08853653.7
申请日：2008-11-27
申请人： Osaka University , Sumitomo Chemical Company, Limited
发明人： ASO, Yoshio , IE, Yutaka , OKABE, Makoto , NITANI, Masashi , UEDA, Masato
IPC分类号： C07D333/22 , C07D277/60 , C07D333/78 , C07D409/14 , C07D417/14 , H01L29/786 , H01L29/80 , H01L51/05 , H01L51/30 , H01L51/42 , H01M14/00
CPC分类号： H01L51/0069 , C07D277/60 , C07D333/22 , C07D333/78 , C07D409/14 , C07D417/14 , C09B3/78 , C09B57/00 , C09B57/001 , H01L51/0036 , H01L51/0558 , Y02E10/549
摘要： 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, R 1 and R 2 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), R 21 and R 22 each independently represent a hydrogen atom, a halogen atom or an optionally substituted monovalent group, and Z 21 and Z 22 , each independently represent any one of the groups represented by the following formulas (α-i)-(α-ix);

wherein R 23 , R 24 , R 25 and R 26 each independently represent a hydrogen atom, a halogen atom or a monovalent group, and R 23 and R 24 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.
摘要翻译：。根据第一发明组，提供具有由下式（I）表示的两个或多个基团或下述通式（II）的共轭化合物：darstellt为6以上的二价芳族烃基和所述worin Ar和Ar的一个” 其他darstellt C 4或更大的二价杂环基，worin所述基团各自可以具有取代基，其条件没有组作为一个整体不含有氟原子，R 1和R 2各自独立地表示氢原子，卤原子或一价基团，Ar“darstellt的三价芳族烃基或三价杂环基;当共轭系化合物具有通式（I）表示的两个或多个基团，不包括论文基的部分不含有氟原子。根据第二组的存在。由下式（±-I）表示的本发明，提供有含氮缩合环化合物：式（±-I）中，R 21和R 22各自独立地表示一个氢原子，取代上任选的卤原子或一价基团，Z 21和Z 22各自独立地表示由下式表示的基团中的任何一个（±-i） - （±-ix）; worin R 23，R 24，R 25和R 26各自unabhängig表示氢原子，卤素原子或一价基团，并且R 23和R 24可以相互结合以形成环，所述左侧和所述右侧组式（±-VIII）表示的可以互换。

5. 发明公开

EP3564245A1 NAPHTHOBISCHALCOGENADIAZOLE DERIVATIVE AND PRODUCTION METHOD THEREFOR 审中-公开
公开(公告)号：EP3564245A1
公开(公告)日：2019-11-06
申请号：EP17889337.6
申请日：2017-10-13
申请人： Osaka University , Ishihara Sangyo Kaisha, Ltd.
发明人： IE, Yutaka , ASO, Yoshio , SEO, Takuji , MORIYAMA, Taichi
IPC分类号： C07D513/04 , C07D517/04
摘要： In order to provide a naphthobischalcogenadiazole derivative that can be used as an intermediate for producing a naphthobischalcogenadiazole compound into which a fluorine atom has been introduced, the naphthobischalcogenadiazole derivative in accordance with an aspect of the present invention is represented by a formula (I):

where each of A 1 and A 2 is independently an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom; and each of X 1 and X 2 is independently a hydrogen atom, a halogen atom, a boronic acid group, a boronic acid ester group, a boronic acid diaminonaphthalene amide group, an N-methyliminodiacetic acid boronate group, a trifluoroborate salt group, or a triolborate salt group.

6. 发明公开

EP1997821A1 FLUORINE-CONTAINING COMPOUND AND METHOD FOR PRODUCING SAME, FLUORINE-CONTAINING POLYMER, ORGANIC THIN FILM, AND ORGANIC THIN FILM DEVICE 审中-公开
标题翻译： FLUOR含有ITS，含氟聚合物，有机薄膜元件及有机薄膜复合AND METHOD
公开(公告)号：EP1997821A1
公开(公告)日：2008-12-03
申请号：EP07714779.1
申请日：2007-02-22
申请人： Osaka University , Sumitomo Chemical Company, Limited
发明人： IE, Yutaka , ASO, Yoshio , NITANI, Masashi , UEDA, Masato
IPC分类号： C07D495/04 , C07D519/00 , C07F7/22 , C08G61/00 , H01L29/786 , H01L51/05 , H01L51/30 , H01L51/42
CPC分类号： H01L51/0039 , C07D495/04 , C07D495/20 , C07D519/00 , C07F7/2212 , C08G61/00 , H01L51/0036 , H01L51/0043 , H01L51/0541 , H01L51/0545 , Y02E10/549 , Y02P70/521
摘要： Fluorinated compounds of the invention are represented by the following general formula (I).

[In formula (I), Ar 1 and Ar 2 each independently represent a C10 or greater aromatic hydrocarbon or C4 or greater heterocyclic group, R 1 represents hydrogen or a monovalent substituent, R 2 and R 3 each independently represent a monovalent substituent, and s1 and t1 each independently represent an integer of 0 or greater. When s1 is 2 or greater, the multiple R 2 groups may be the same or different, and when t1 is 2 or greater the multiple R 3 groups may be the same or different.]
摘要翻译：本发明的氟化化合物由下述通式（I）表示。 [在式（I）中，Ar 1和Ar 2各自独立地表示C 10以上的芳烃基或C4或更高的杂环基，R 1个darstellt氢或一价取代基，R 2和R 3各自独立地表示一价取代基，并 S1和T1每个unabhängig在0或更大的整数代表。当S1为2或更大时，多个存在的R 2基团可以是相同的或不同的，且当t1为2或更大时多个R 3基团可以相同或不同。]

7. 发明公开

EP1878736A1 COATED HETEROAROMATIC RING COMPOUND 审中-公开
标题翻译： VERBINDUNG MIT BESCHICHTETEM HETEROAROMATISCHEM RING
公开(公告)号：EP1878736A1
公开(公告)日：2008-01-16
申请号：EP06715077.1
申请日：2006-03-02
申请人： OSAKA UNIVERSITY , Japan Science and Technology Agency
发明人： ASO, Yoshio , IE, Yutaka , HAN, Aihong
IPC分类号： C07F7/18
CPC分类号： C07F7/1856 , C07F7/1844 , C08G61/123 , C08G61/124 , C08G61/125 , C08G61/126 , C09D165/00 , C09K11/06 , C09K2211/1458 , H01L51/0036 , H01L51/0068 , H01L51/0094 , H05B33/14
摘要： The present invention provide a covered heteroaromatic ring compound whose hetero ring effectively is covered and that is suitable for electronic materials and the like. For example, following Scheme 1 below, first, a thiophene monomer unit (1T) is synthesized, and then oligomers (2T) to (16T) are synthesized by repeating oxidative polymerization. The hetero ring is not limited to thiophene, and may be furan or pyrrole, for example. Also, substituents on silicon are not limited to those in Scheme 1, and any substituents may be used. The degree of polymerization and the synthesis method are not limited to those in Scheme 1. In the compound of the present invention, π electronic conjugation effectively is kept as shown in the ultraviolet and visible absorption spectrum in FIG. 1, for example. Accordingly, the compound is useful, for example, as a research tool for clarifying electrical properties according to the degree of polymerization of oligoheterocyclic compounds, and as molecular wires that are important in molecular electronics devices.
摘要翻译：本发明提供一种被覆盖的杂环芳族化合物，其杂环有效地被覆盖并且适用于电子材料等。例如，按照下面的方案1，首先合成噻吩单体单元（1T），然后通过重复氧化聚合合成低聚物（2T）至（16T）。异环不限于噻吩，例如可以是呋喃或吡咯。此外，硅上的取代基不限于方案1中的取代基，并且可以使用任何取代基。聚合度和合成方法不限于方案1中的方法。在本发明的化合物中，电子共轭有效地保持在图1中的紫外和可见吸收光谱中。 1，例如。因此，该化合物可用作例如根据低聚杂环化合物的聚合度以及分子电子器件中重要的分子线来澄清电性能的研究工具。

8. 发明公开

EP2251335A1 BRANCHED COMPOUNDS, ORGANIC THIN FILMS MADE BY USING THE SAME, AND ORGANIC THIN FILM DEVICES 审中-公开
标题翻译： VERZWEIGTE VERBINDUNGEN，DAMN HERGESTELLTE ORGANISCHEDÜNNSCHICHTENUND ORGANISCHEDÜNNSCHICHTELEMENTE
公开(公告)号：EP2251335A1
公开(公告)日：2010-11-17
申请号：EP09709735.6
申请日：2009-01-07
申请人： Osaka University , Sumitomo Chemical Company, Limited
发明人： IE, Yutaka , UTO, Toshihiko , ASO, Yoshio , UEDA, Masato
IPC分类号： C07D333/16 , C07D333/08 , C07D333/12 , C07D409/14 , C07D471/04 , H01L29/786 , H01L51/05 , H01L51/30 , H01L51/42
CPC分类号： C07D333/08 , B82Y10/00 , C07D333/12 , C07D333/16 , C07D409/14 , C07D471/04 , H01L51/0047 , H01L51/0053 , H01L51/0068 , H01L51/0095 , H01L51/0512 , H01L51/0558 , Y02E10/549
摘要： A branched compound including a core part, at least one side chain part bonded to the core part, and an end, wherein one repeating unit or two or more repeating units expressed by the following formula (1) repeat in the or each side chain part, with the proviso that in a repeating unit bonded to the core part, T is bonded to the core part, and in two or more contiguous repeating units, each L is bonded to the T, each L is formed of a plurality of conjugation-forming units linked together; each L includes at least one thienylene unit as the conjugation-forming unit; and at least two of the groups existing at the ends of Ls (the ends of the L in sides which are not bonded to T) are acceptor groups.

(In the formula, each L represents a divalent organic group which may have a substituent and the T represents a trivalent organic group which may have a substituent.)
摘要翻译：一种支链化合物，其包含核心部分，至少一个侧链部分与核心部分结合，以及末端，其中一个重复单元或两个或更多个由下式（1）表示的重复单元在该侧链或各侧链部分中重复条件是在与核心部分结合的重复单元中，T结合到核心部分，并且在两个或更多个连续重复单元中，每个L结合到T，每个L由多个共轭 - 形成单元连接在一起; 每个L包括至少一个噻吩基单元作为共轭形成单元; 并且存在于Ls的末端的两个组中的至少两个（L侧不与T结合的端部）是受体组。（式中，L表示可以具有取代基的二价有机基团，T表示可具有取代基的三价有机基团。）

9. 发明公开

EP2407465A1 CONJUGATED COMPOUND, AND ORGANIC THIN FILM AND ORGANIC THIN FILM ELEMENT EACH COMPRISING SAME 审中-公开
标题翻译：共轭化合物以及有机薄膜以及有机薄膜元素
公开(公告)号：EP2407465A1
公开(公告)日：2012-01-18
申请号：EP10750884.8
申请日：2010-03-10
申请人： Sumitomo Chemical Company, Limited , Osaka University
发明人： IE, Yutaka , OKABE, Makoto , ASO, Yoshio , UEDA, Masato
IPC分类号： C07D333/78 , H01L29/786 , H01L29/80 , H01L51/05 , H01L51/30 , H01L51/42
CPC分类号： H01L51/0068 , C07D333/78 , C07D495/04 , C07D495/14 , C09B3/78 , C09B23/0058 , C09B23/04 , C09B57/00 , C09B57/001 , H01L51/0036 , H01L51/0051 , H01L51/0074 , H01L51/008 , H01L51/0541 , Y02E10/549
摘要： A conjugated compound having a group represented by formula (I) and/or formula (II).

[In the formulas, Ar represents an optionally substituted trivalent aromatic hydrocarbon or optionally substituted trivalent heterocyclic group, and A represents hydrogen, a halogen atom or a monovalent group. When multiple A groups are present they may be the same or different, and at least one A represents an electron-withdrawing group. Ar' represents an optionally substituted C6 or greater divalent aromatic hydrocarbon or optionally substituted C4 or greater divalent heterocyclic group, and R 1 and R 2 are the same or different and each represents hydrogen, a halogen atom or a monovalent group, while A' represents hydrogen, a halogen atom or a monovalent group. When multiple A' groups are present they may be the same or different, and at least one A' represents an electron-withdrawing group.]
摘要翻译：具有由式（I）表示的基团和/或式（II）的共轭化合物。 [式中，Ar darstellt到任选substituiertem三价芳族烃基或三价杂环基可以substituiertem，和A darstellt氢，卤原子或一价基团。当多个基团存在甲它们可以是相同或不同的，和至少一个吸电子基团的甲darstellt。中，Ar“darstellt到任选substituiertem C6以上的2价的芳香族烃或任选substituiertem C4以上的2价的杂环基，和R 1和R 2是相同或不同，并且各自darstellt氢，卤原子或一价基团，而A” darstellt 氢，卤原子或一价基团。当多个A“基团存在时，它们可以相同或不同，并且至少一个A” darstellt吸电子基团的。]

10. 发明公开

EP2243796A1 POLYMER, ORGANIC THIN FILM USING THE SAME, AND ORGANIC THIN FILM DEVICE 审中-公开
标题翻译：聚合物，有机加工聚合物生物技术有限公司DÜNNSCHICHTVORRICHTUNG
公开(公告)号：EP2243796A1
公开(公告)日：2010-10-27
申请号：EP09711231.2
申请日：2009-02-09
申请人： Osaka University , Sumitomo Chemical Company, Limited
发明人： KARAKAWA, Makoto , ASO, Yoshio , UEDA, Masato
IPC分类号： C08G61/12 , H01L29/786 , H01L51/05 , H01L51/30 , H01L51/40 , H01L51/42
CPC分类号： H01L51/0036 , C08G61/126 , C08G2261/312 , C08G2261/3223 , C08G2261/91 , C08G2261/92 , C08G2261/94 , H01L51/0043 , H01L51/0541 , H01L51/0545
摘要： A polymer according to the present invention comprises a repeating structure represented by the following formula (1), wherein L and X each independently have a configuration in which are linked a plurality of conjugation forming structures each conjugated by itself, and each have at least one thienylene structure as the conjugation forming structure:

wherein each X represents a monovalent organic group that may have a substituent, each L represents a divalent organic group that may have a substituent, and each T represents a trivalent organic group that may have a substituent, with the proviso that in the formula, the X's represent the same group, the L's represent the same group, and the T's represent the same group.
摘要翻译：根据本发明的聚合物包含由下式（1）表示的重复结构，其中L和X各自独立地具有连接多个共轭形成结构的结构，每个共轭形成结构各自结合，并且各自具有至少一个噻吩基结构作为共轭形成结构：其中每个X表示可以具有取代基的一价有机基团，每个L表示可以具有取代基的二价有机基团，并且每个T表示可以具有取代基的三价有机基团，条件是在公式中，X代表同一组，L代表同一组，T代表同一组。

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