KR970028877A - 규소계 정공 전송재의 제조방법 - Google Patents

규소계 정공 전송재의 제조방법 Download PDF

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KR970028877A
KR970028877A KR1019960052206A KR19960052206A KR970028877A KR 970028877 A KR970028877 A KR 970028877A KR 1019960052206 A KR1019960052206 A KR 1019960052206A KR 19960052206 A KR19960052206 A KR 19960052206A KR 970028877 A KR970028877 A KR 970028877A
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silicon
hole transport
transport material
group
platinum compound
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KR100445711B1 (ko
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노부오 구시비키
기쿠코 다케우치
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마쓰무라 다다시
다우 코닝 아시아, 리미티드
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0614—Amines
    • G03G5/06142—Amines arylamine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/1876—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-C linkages
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
    • G03G5/0528—Macromolecular bonding materials
    • G03G5/0557—Macromolecular bonding materials obtained otherwise than by reactions only involving carbon-to-carbon unsatured bonds
    • G03G5/0578—Polycondensates comprising silicon atoms in the main chain
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0614—Amines
    • G03G5/06142—Amines arylamine
    • G03G5/06144—Amines arylamine diamine
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0614—Amines
    • G03G5/06142—Amines arylamine
    • G03G5/06144—Amines arylamine diamine
    • G03G5/061443—Amines arylamine diamine benzidine
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0614—Amines
    • G03G5/06142—Amines arylamine
    • G03G5/06147—Amines arylamine alkenylarylamine
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0614—Amines
    • G03G5/06142—Amines arylamine
    • G03G5/06147—Amines arylamine alkenylarylamine
    • G03G5/061473—Amines arylamine alkenylarylamine plural alkenyl groups linked directly to the same aryl group
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/07—Polymeric photoconductive materials
    • G03G5/078—Polymeric photoconductive materials comprising silicon atoms

Abstract

본 발명은 폴리실록산 수지에 전하 전송능을 부여하고, 수지에 가용성인 정공 전송재(charge transporting materials)를 제조하는 방법에 관한 것이다. 정공 전송재는 다수의 방향족 그룹, 및 이들 방향족 그룹 중의 하나 이상에 탄화수소 그룹을 통해 도입되는 실릴 그룹을 갖는 방향족 치환된 3급 아민이다. 당해 방법은 규소계 정공 전송성 화합물을 구성하는 방향족 그룹에 결합되어 있는 불포화 지방족 그룹을 사용하거나, 규소에 대한 치환체가 수소원자 또는 가수분해 가능한 그룹인 실란에 결합되어 있는 신규하게 결합된 불포화 지방족 그룹을 사용한다. 당해 방법은 촉매로서 백금 화합물의 존재하에 하이드로실릴화에 의해서 수행된다. 이후에, 규소계 정공 전송재를 백금 화합물에 대한 흡착재와 접촉시켜서 백금 화합물이 흡착재 위에 흡착되도록 한다. 백금 화합물을 흡착재와 함께 제거하여 잔류하는 백금 화합물의 농도가 10ppm 미만이 되게 한다.

Description

규소계 정공 전송재의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (7)

  1. 촉매로서의 하이드로실릴화 백금 화합물의 존재하에 탄화수소 그룹을 사용하여, 이온화 전위 범위가 4.5 내지 6.2eV인 전하 전송성 화합물의 방향족 그룹 중의 하나 이상의 방향족 환에 실릴 그룹을 도입시키고, 규소계 정공 전송재를 백금 화합물용 흡착재와 접촉시켜 백금 화합물을 흡착재에 흡착시킨 다음, 규소계 정공 전송재로부터 백금 화합물과 흡착재를 분리시킴으로써 규소계 정공 전송재 중의 잔류 백금 화합물의 농도가 10ppm 미만으로 되도록 함을 포함하여, 가수분해 가능한 그룹 Q를 함유하는 실릴 그룹과 다수의 방향족 그룹을 갖는 방향족 치환된 3급 아민임을 특징으로 하는 화학식 (1)의 규소계 정공 전송재를 제조하는 방법.
    A-[R1SiR2 3-nQn]p(1)
    상기 화학식 (1)에서, A는 다수의 방향족 그룹을 갖는 방향족 치환된 3급 아민으로서, 이온화 전위 범위가 4.5 내지 6.2eV인 전하 전송성 화합물로부터 유도된 유기 그룹이고, R1은 탄소수 1 내지 18의 알킬렌 그룹이며, R2는 탄소수 1 내지 15의 1가 탄화수소 그룹 또는 할로겐 치환된 1가 탄화수소 그룹이고, Q는 가수분해 가능한 그룹이며, n 및 p는 각각 1 내지 3이다.
  2. 제1항에 있어서, 가수분해 가능한 그룹 Q가 알콕시 그룹인 방법.
  3. 제2항에 있어서, 전하 전송성 화합물의 방향족 그룹의 일부 또는 전부가 불포화 탄화수소 그룹 형태의 치환체[여기서, 치환체는 알콕시실란을 사용하여 하이드로실릴화합으로써 화학식 (1)의 규소계 정공 전송재를 수득한다]를 갖는 방법.
  4. 제1항에 있어서, 흡착재가 규소계 정공 전송재에 대하여 불활성이고, 활성탄, 실리카 겔 및 다공성 알루미나로 이루어진 그룹으로부터 선택되는 방법.
  5. 제1항에 있어서, 규소계 정공 전송재가 용해된 용액으로서의 규소계 정공 전송재가 흡착재와 접촉되고, 용액을 흡착재로 충전된 칼럼을 통과시킴으로써 백금 화합물이 규소졔 정공 전송재로부터 분리되는 방법.
  6. 제1항에 따르는 방법으로 수득한 규소계 정공 전송재.
  7. 촉매로서의 하이드로실릴화 백금 화합물의 존재하에, 방향족 환에 치환된 비닐 그룹을 갖는 전하 전송성 화합물의 방향족 환과 규소에 결합된 수소원자를 갖는 유기 규소 화합물의 규소원자 사이에 탄화수소 그룹을 도입시키고, 규소계 정공 전송재를 백금 화합물용 흡착재와 접촉시켜 백금 화합물을 흡착재에 흡착시킨 다음, 규소계 정공 전송재로부터 백금 화합물과 흡착재를 분리시킴으로써 규소계 정공 전송재 중의 잔류 백금 화합물의 농도가 10ppm 미만으로 되도록 함을 포함하여, 화학식 (1)의 규소계 정공 전송재를 제조하는 방법.
    A-[R1SiR2 3-nQn]p(1)
    상기 화학식 (1)에서, A는 다수의 방향족 그룹을 갖는 방향족 치환된 3급 아민으로서, 이온화 전위 범위가 4.5 내지 6.2eV인 전하 전송성 화합물로부터 유도된 유기 그룹이고, R1은 탄소수 1 내지 18의 알킬렌 그룹이며, R2는 탄소수 1 내지 15의 1가 탄화수소 그룹 또는 할로겐 치환된 1가 탄화수소 그룹이고, Q는 가수분해 가능한 그룹이며, n 및 p는 각각 1 내지 3이다.
    ※ 참고사항:최초출원 내용에 의하여 공개하는 것임.
KR1019960052206A 1995-11-06 1996-11-06 규소계정공전송재및이의제조방법 KR100445711B1 (ko)

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JP95-287644 1995-11-06
JP28764495A JP3614222B2 (ja) 1995-11-06 1995-11-06 ケイ素系正孔輸送材の製造方法

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US (1) US5688961A (ko)
EP (1) EP0771807B1 (ko)
JP (1) JP3614222B2 (ko)
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CN (1) CN1067398C (ko)
AU (1) AU707231B2 (ko)
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TW (1) TW349186B (ko)

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CN1067398C (zh) 2001-06-20
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DE69619465T2 (de) 2002-10-17
AU707231B2 (en) 1999-07-08
US5688961A (en) 1997-11-18
CN1150591A (zh) 1997-05-28
AU7059496A (en) 1997-05-15
JP3614222B2 (ja) 2005-01-26
EP0771807A1 (en) 1997-05-07

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