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    TETRATHIAFULVALENYL GROUP-CONTAINING DIACETYLENE DERIVATIVE AND ITS PRODUCTION
    31.
    发明专利
    TETRATHIAFULVALENYL GROUP-CONTAINING DIACETYLENE DERIVATIVE AND ITS PRODUCTION 失效

    公开(公告)号：JPH09227552A

    公开(公告)日：1997-09-02

    申请号：JP4274896

    申请日：1996-02-29

    Applicant: AGENCY IND SCIENCE TECHN

    Inventor： SHIMADA SATORU ,  MATSUDA HIROO ,  OKADA SHUJI ,  NAKANISHI HACHIRO

    IPC: G03C1/73 ,  C07D339/06 ,  C08F38/02 ,  G02B1/04

    Abstract: PROBLEM TO BE SOLVED: To obtain a new compound useful as a raw material for a functional material such as nonlinear optical material, photosensitive material, polymer semiconductor crystal, etc., having solid-phase polymerizability. SOLUTION: This diacetylene derivative is shown by formula I (Ar is a bifunctional aromatic group; (m) and (n) are each 2-12). The compound of formula I is obtained by reacting a 1,3-alkadiynecarboxylic acid amide compound of the formula, CH3 -(CH2 )m-C≡C-C≡C-(CH2 )n -CONH-Ar-COOH or its acid halide with hydroxymethyltetrathiafulvalene of formula II in an inert gas atmosphere (e.g. nitrogen gas) in a solvent (e.g. methylene chloride) at 0-50 deg.C. The 1,3-alkadiynecarboxylic acid amide compound is obtained by reacting an 1,3- alkadiynecarboxylic acid compound of the formula, CH3 -(CH2 )m - C≡C-C≡C-(CH2 )n -COOR (R is H or a halogen) with an aromatic aminocarboxylic acid ester of the formula, H2 N-Ar-COOR (R is a hydrocarbon) and hydrolyzing the ester bond.

    DIACETYLENE DERIVATIVE AND PRODUCTION THEREOF
    32.
    发明专利
    DIACETYLENE DERIVATIVE AND PRODUCTION THEREOF 失效

    公开(公告)号：JPH07233141A

    公开(公告)日：1995-09-05

    申请号：JP5133894

    申请日：1994-02-23

    Applicant: AGENCY IND SCIENCE TECHN

    Inventor： SHIMADA SATORU ,  MATSUDA HIROO ,  MINAMI SHINJI ,  OKADA SHUJI ,  NAKANISHI HACHIRO

    IPC: C07C319/18 ,  C07C319/14 ,  C07C323/19

    Abstract: PURPOSE:To obtain a diacetylene derivative which has an S atom directly bonded to a C atom in the triple bond and shows a large electronic effect and solid-phase polymerizability, thus is useful as a functional material such as a nonlinear optical material, a photosensitive material and a polymer semiconductor crystal. CONSTITUTION:The compound of formula I [Ar , Ar are (substituted) phenyl; n is 1-8], for example, 8-(4-bromophenyl)thio-5,7-octadiynyl phenylcarbamate. The compound of formula I is prepared by protecting the terminal hydroxy group in omega-hydroxy-1,3-alkadiyne of formula II, introducing an arylthio group into the 1-position of the protected omega-hydroxy-1,3-alkadiyne, deprotecting the product of the diacetylene derivative of formula III and allowing the deprotected hydroxyl to react with an aryl isocyanate to effect introduction of a urethane group on the chain terminal.

    NONLINEAR OPTICAL ORGANIC MATERIAL
    35.
    发明专利
    NONLINEAR OPTICAL ORGANIC MATERIAL 失效

    公开(公告)号：JPH0192727A

    公开(公告)日：1989-04-12

    申请号：JP12285188

    申请日：1988-05-19

    Applicant: AGENCY IND SCIENCE TECHN

    Inventor： OKADA SHUJI ,  MATSUDA HIROO ,  NAKANISHI HACHIRO ,  KATO MASAO ,  SAMURA HIDEO

    IPC: C09K3/00 ,  C07C67/00 ,  C07C209/00 ,  C07C211/52 ,  G02F1/35 ,  G02F1/355 ,  G02F1/361

    Abstract: PURPOSE:To obtain a nonlinear optical org. material which has the second harmonic waves generation as large as several times that of urea, is stable at room temp. and is easily growable to a large single crystal by using specific 4-amino-4'-nitrobiphenyl as said org. material. CONSTITUTION:The 4-amino-4'-nitrobiphenyl expressed by the formula I is the single crystal without having a symmetrical center and, therefore, exhibits the second harmonic wave generation (SGH) activity of several times that of urea and is stable at room temp. Said material generates the second harmonic waves (SHG) and generates green light of the wavelength (532mum) of half the wavelength of incident light when measurement is made by projection of Nd: YAG laser (wavelength = 1064mum, output 3mJ/pulse) in the powder state. This material is growable to a single crystal of mm order. The org. crystal which has the large SHG activity, is stable at room temp. and is easily growable to the large single crystal at need is thereby obtd. This crystal is adequate as a material for light wavelength conversion elements, optical shutters, high- speed optical switching elements and optical logical gates as well as the stock for optical transistors, etc.

    NONLINEAR OPTICAL ORGANIC MATERIAL
    37.
    发明专利
    NONLINEAR OPTICAL ORGANIC MATERIAL 失效

    公开(公告)号：JPS6259934A

    公开(公告)日：1987-03-16

    申请号：JP19970585

    申请日：1985-09-10

    Applicant: AGENCY IND SCIENCE TECHN

    Inventor： OKADA SHUJI ,  MATSUDA HIROO ,  NAKANISHI HACHIRO ,  KATO MASAO ,  SAMURA HIDEO

    IPC: G02F1/35 ,  C07C211/42 ,  G02F1/313 ,  G02F1/355 ,  G02F1/361

    Abstract: PURPOSE:To obtain the titled material having a large 2nd high frequency generating capacity (SHG) and a high stability at a room temp. and a large-sized monocrystal by incorporating a specific org. compd. to the titled material. CONSTITUTION:The titled material comprises a 2-amino fluorenone shown by formula I or a 4-amino-4'-nitrobiphenyl shown by formula II. The prescribed compds. may grow to the large monocrystal by a slow evaporation method. The prescribed compds. has a SHG larger than that of an urea by few times and has a good stability at the room temp. and may be easily grown to the large monocrystal. Thus, the titled material is used for materials of an optical wavelength conversion element, an optical shutter, a high switching element, a optical logical gate and an phototransistor.

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