JPH02135361A - Electrophotographic sensitive body - Google Patents

Electrophotographic sensitive body

Info

Publication number
JPH02135361A
JPH02135361A JP63287618A JP28761888A JPH02135361A JP H02135361 A JPH02135361 A JP H02135361A JP 63287618 A JP63287618 A JP 63287618A JP 28761888 A JP28761888 A JP 28761888A JP H02135361 A JPH02135361 A JP H02135361A
Authority
JP
Japan
Prior art keywords
group
electrophotographic photoreceptor
charge
photosensitive layer
layer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
JP63287618A
Other languages
Japanese (ja)
Inventor
Yutaka Akasaki
赤崎　豊
Katsumi Nukada
克己 額田
Katsuhiro Sato
克洋 佐藤
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fujifilm Business Innovation Corp
Original Assignee
Fuji Xerox Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Fuji Xerox Co Ltd filed Critical Fuji Xerox Co Ltd
Priority to JP63287618A priority Critical patent/JPH02135361A/en
Priority to US07/436,875 priority patent/US5011757A/en
Priority to US07/506,602 priority patent/US5075487A/en
Publication of JPH02135361A publication Critical patent/JPH02135361A/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/61—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by doubly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/34—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by unsaturated carbon chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/35—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/40—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by doubly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C07C49/683—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
    • C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/57—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • 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
    • G03G5/0609—Acyclic or carbocyclic compounds containing oxygen
    • 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
    • G03G5/0618—Acyclic or carbocyclic compounds containing oxygen and nitrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

Abstract

PURPOSE:To obtain an electrophotographic sensitive body having superior electrophotographic characteristics by incorporating a specified compd. as charge transfer material of a photosensitive layer. CONSTITUTION:A compd. expressed by the formula I is incorporated as charge transfer material of a photosensitive layer formed on an electroconductive base body. In the formula I, each R1 and R2 is an H atom, alkyl group, aryl group, alkoxycarbonyl group, aryloxycarbonyl group, nitro group, halogen atom, alkylcarbonyl group or arylcarbonyl group; R3 is a (substituted)aryl or N-contg. heterocyclic group; (m) is zero or 1; (n) is zero-2. Thus, an electrophotographic sensitive body having superior electrophotographic characteristics is obtd.

Description

【発明の詳細な説明】 産業上の利用分野 本発明は、静電潜像を形成させるための電子写真感光体
に関する。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to an electrophotographic photoreceptor for forming an electrostatic latent image.

従来の技術 従来、有機光導電体を用いた電子写真感光体は、無公害
、高生産性、低コスト等の利点があるため、種々研究さ
れており、感光層に増感材としてジフェニルジシアノエ
チレン誘導体を用いたものも知られている（例えば、特
開昭５４−３０８３４号公報参照）。Conventional technology Conventionally, electrophotographic photoreceptors using organic photoconductors have been studied in various ways because they have advantages such as non-pollution, high productivity, and low cost. Those using derivatives are also known (see, for example, Japanese Patent Application Laid-Open No. 54-30834).

ところで有機光導電体のうち、可視光を吸収して電荷を
発生する物質は、電荷保持力に乏しく、逆に、電荷保持
力が良好で、成膜性に優れた物質は、一般に可視光によ
る光導電性がほとんど無いという欠点がある。この問題
を解決するために、感光層を可視光を吸収して電荷を発
生する電荷発生材と、その電荷の輸送を行う電荷輸送材
とに機能分離した層構成を有する積層型の感光層とする
ことが行われている。そして、電荷発生材及び電荷輸送
材については、数多くのものが提案されている。そして
正孔輸送材としては、アミン化合物、ヒドラゾン化合物
、ピラゾリン化合物、オキサゾール化合物、オキサジア
ゾール化合物、スチルベン化合物、カルバゾール化合物
等が知られており、又、電子輸送材としては、２，４．
７−ドリニトロフルオレノン等がおる。その他、例えば
、特公昭４８−９９８８号公報及びカナダ特許第９１２
０１９号明細書にはボロンを含む化合物が記載されてい
る。By the way, among organic photoconductors, materials that absorb visible light and generate electric charge have poor charge retention ability, whereas materials that have good charge retention ability and excellent film forming properties generally cannot be used with visible light. The drawback is that it has almost no photoconductivity. In order to solve this problem, we developed a laminated photosensitive layer that has a layer structure in which the photosensitive layer is functionally separated into a charge-generating material that absorbs visible light and generates a charge, and a charge-transporting material that transports the charge. things are being done. Many charge generating materials and charge transporting materials have been proposed. As hole transport materials, amine compounds, hydrazone compounds, pyrazoline compounds, oxazole compounds, oxadiazole compounds, stilbene compounds, carbazole compounds, etc. are known, and as electron transport materials, 2, 4.
7-Dolinitrofluorenone, etc. Others, for example, Japanese Patent Publication No. 48-9988 and Canadian Patent No. 912
No. 019 describes compounds containing boron.

発明が解決しようとする課題 ところで、有機光導電体を用いた単層構造の電子写真感
光体においては、増感材として充分実用的なものは未だ
知られていない。又、積層構造の機能分離型電子写真感
光体においては、コロトロンにおけるオゾンの発生防止
、現像におけるトナーの帯電制御等の点から、正帯電型
の方が望ましい。ところが、正帯電型として用いる場合
、電荷輸送材が正孔輸送性の場合、電荷発生層を上層と
する必要があるが、電荷発生層はその性質上、薄膜化さ
せるのが通常でおり、感光体としての機械的特性を満足
させるには不充分でおる。又、負帯電で用いるための複
写機側の工夫も必要である。Problems to be Solved by the Invention However, as for electrophotographic photoreceptors with a single layer structure using an organic photoconductor, a sufficiently practical sensitizing material is not yet known. In addition, in a function-separated type electrophotographic photoreceptor having a laminated structure, a positively charged type is preferable from the viewpoints of preventing ozone generation in the corotron, controlling toner charge during development, and the like. However, when used as a positively charged type, if the charge transport material has hole transport properties, it is necessary to provide a charge generation layer as an upper layer. It is insufficient to satisfy the mechanical properties of the body. In addition, it is necessary to devise measures on the copying machine side for use with negative charging.

そこで比較的厚膜の電荷輸送層を上層として正帯電性の
感光体を得たいという要望も一方におり、そのためには
、電荷輸送層において、電子輸送性の電荷輸送材を用い
ることが必要である。しかしながら、従来提案されてい
る電子輸送性の電荷輸送材で充分有効なものは知られて
いない。Therefore, there is a desire to obtain a positively charged photoreceptor with a relatively thick charge transport layer as an upper layer, and to achieve this, it is necessary to use a charge transport material with electron transport properties in the charge transport layer. be. However, none of the previously proposed charge transport materials with electron transport properties are known to be sufficiently effective.

本発明は、従来の上記のような問題点に鑑みてなされた
ものである。The present invention has been made in view of the above-mentioned conventional problems.

したがって、本発明の目的は、優れた電子写真特性を有
する電子写真感光体を提供することにある。Therefore, an object of the present invention is to provide an electrophotographic photoreceptor having excellent electrophotographic properties.

本発明の他の目的は、優れた電子写真特性を有する正帯
電用の積層型電子写真感光体を提供することにある。Another object of the present invention is to provide a laminated electrophotographic photoreceptor for positive charging that has excellent electrophotographic properties.

課題を解決するための手段 本発明者等は、研究の結果、−群のフルオレノン誘導体
を増感材又は電荷輸送材として用いると、良好な電子写
真特性を示す電子写真感光体が得られることを見出だし
、本発明を完成するに至った。Means for Solving the Problems As a result of research, the present inventors have found that an electrophotographic photoreceptor exhibiting good electrophotographic properties can be obtained by using -group fluorenone derivatives as a sensitizing material or a charge transporting material. This heading led to the completion of the present invention.

本発明の電子写真感光体は、導電性支持体上に、感光層
を有し、そして、感光層が、電荷輸送材として下記−投
銭（Ｉ＞で示される化合物を含有してなることを特徴と
する。The electrophotographic photoreceptor of the present invention is characterized in that it has a photosensitive layer on a conductive support, and the photosensitive layer contains a compound represented by the following I as a charge transporting material. shall be.

示される。shown.

（式中、Ｒ１及びＲ２は、それぞれ水素原子、アルキル
基、アリール基、アリールカルボニル基、アリールオキ
シカルボニル基、ニトロ基、ハロゲン原子、アルキルカ
ルボニル基又はアリールカルボニル基を示し、Ｒ３は置
換されていてもよいアルール基又は含窒素複素環基を示
し、ｍは０又は１を示し、ｎはＯ〜２を示す） 本発明において用いられる上記一般式（Ｉ）で示される
化合物としては、例えば、次のものが例Ｏ これらの化合物は、下記反応式で示すように、−投銭（
ｎ）で示されるフルオレノンカルボン酸を酸クロライド
化し、−投銭Ｒ３Ｈで示される化合物と反応させること
によって得ることができる。(In the formula, R1 and R2 each represent a hydrogen atom, an alkyl group, an aryl group, an arylcarbonyl group, an aryloxycarbonyl group, a nitro group, a halogen atom, an alkylcarbonyl group, or an arylcarbonyl group, and R3 is substituted. (m represents 0 or 1, n represents O-2) The compounds represented by the above general formula (I) used in the present invention include, for example, the following: Example O These compounds, as shown in the reaction formula below, have the following reaction:
It can be obtained by acid chloridizing the fluorenone carboxylic acid represented by n) and reacting it with the compound represented by -R3H.

（式中、Ｒ１、Ｒ２、Ｒ３、ｍ及びｎ　ハ、上記の定義
と同一である） 次に、上記化合物のうちの代表的なものについて合成例
を示すが、本発明において使用するその他のフルオレン
誘導体も下記の方法に準じて同様に合成することができ
る。(In the formula, R1, R2, R3, m and n are the same as defined above.) Next, synthesis examples will be shown for representative compounds among the above compounds. Derivatives can also be similarly synthesized according to the method below.

（合成例１）　例示化合物（３）の合成５００ｍ、ｌｌ
の三つロフラスコに、９−フルオレノ−４−カルボン１
２５．Ｏｇ（ｌｌｌｍｍｏｌ）及び塩化チオニル３００
ｍ、ｌｌを入れ、窒素気流下で５時間還流した後、塩化
チオニルを減圧留去し、更に残漬に１，２−ジクロロエ
タン１００ｍ、ｌｌを加えて減圧留去し、残留する塩化
チオニルを除いた。生成した酸クロライドに、塩化メヂ
レン２００ｍｆｌを加え、冷浴で一２０℃に冷却し、塩
化アルミニウム２０．０！？　（１５０ｍｍｏｌ）を加
え、窒素気流下、１５時間Ｉａ拝した。その後、ｎ−ブ
チルベンゼン１５．９ｙ　（１１８ｍｍｏｌ）と塩化メ
チレン５０　ｍＦよりなる溶液を３０分間掛けて滴下し
た。滴下終了後、３時間そのまま瞳拌を続け、次いで冷
浴を除き、空温で２０時間隈拝金続けた。更に７．５ｇ
（５６，３ｍｍｏ　ｌ　）を加え、２，５時間攪拌した
後、氷１５０３上に投入し、２０％水酸化カリウム溶液
を水酸化アルミニウムが溶けるまで加え、有機層を分離
した。水層を塩化メチレンで抽出し、得られた有機層を
合わせて、溶剤を減圧留去した。残渣に５％水酸化カリ
ウム２００ｍ、ｌ！を加え、８０℃で加熱して残留する
酸クロライドを分解した後、生成物を塩化メチレンで抽
出した。シリカゲルショートカラム（塩化メチレンで溶
出）で精製し、溶媒を留去した後、ヘキサン、続いて酢
酸エチルで再結晶して例示化合物（３）　１３．８ｇ（
収率３６．４％）を黄色粉末として得た。融点９３〜９
５℃。(Synthesis Example 1) Synthesis of Exemplary Compound (3) 500m, ll
In a three-necked flask, add 9-fluoreno-4-carvone 1
25. Og (llmmol) and thionyl chloride 300
After refluxing for 5 hours under a nitrogen atmosphere, thionyl chloride was distilled off under reduced pressure, and 100 m and 1 of 1,2-dichloroethane was added to the residue and evaporated under reduced pressure to remove the remaining thionyl chloride. Ta. 200 mfl of methylene chloride was added to the produced acid chloride, and the mixture was cooled to -20°C in a cold bath, resulting in aluminum chloride of 20.0 mfl. ? (150 mmol) was added, and the mixture was stirred for 15 hours under a nitrogen stream. Thereafter, a solution consisting of 15.9y (118 mmol) of n-butylbenzene and 50 mF of methylene chloride was added dropwise over 30 minutes. After completion of the dropwise addition, pupil stirring was continued for 3 hours, and then the cold bath was removed and kumaikan was continued for 20 hours at air temperature. Another 7.5g
(56.3 mmol) and stirred for 2.5 hours, poured onto ice 1503, 20% potassium hydroxide solution was added until aluminum hydroxide was dissolved, and the organic layer was separated. The aqueous layer was extracted with methylene chloride, the resulting organic layers were combined, and the solvent was distilled off under reduced pressure. Add 200ml, l of 5% potassium hydroxide to the residue! was added and heated at 80°C to decompose the remaining acid chloride, and then the product was extracted with methylene chloride. After purification with a silica gel short column (eluted with methylene chloride) and distilling off the solvent, recrystallization was performed with hexane and then with ethyl acetate to obtain 13.8 g of Exemplified Compound (3) (
Yield: 36.4%) was obtained as a yellow powder. Melting point 93-9
5℃.

（合成例２）　例示化合物（５）の合成ｎ−ブチルベン
ゼンの代わりにビフェニルを用いる以外は、合成例１に
おけると同様に処理して例示化合物（５）を黄色針状結
晶として得た。融点１５４、５〜１５６℃ （合成例３）　例示化合物（７）の合成ローブチルベン
ゼンの代わりにペンチルビフェニルを用いる以外は、合
成例１におけると同様に処理して目的のフルオレン化合
物（例示化合物７）を淡黄色板状結晶として得た。融点
１５１．５〜１５３°Ｃ 本発明の電子写真感光体において、導電性支持体として
は、例えば、金属パイプ、金属板、金属シート、金属箔
、導電処理を施した高分子フィルム、ＡＩ等の金属の蒸
着層を設けた高分子フィルム、ＳｎＯ，等の金属酸化物
、第４級アンモニウム塩等により被覆された高分子フィ
ルム又は紙等が用いられる。(Synthesis Example 2) Synthesis of Exemplified Compound (5) Exemplified Compound (5) was obtained as yellow needle-like crystals by the same procedure as in Synthesis Example 1, except that biphenyl was used instead of n-butylbenzene. Melting point 154, 5-156°C (Synthesis Example 3) Synthesis of Exemplified Compound (7) The desired fluorene compound (Exemplified Compound 7 ) was obtained as pale yellow plate-like crystals. Melting point: 151.5 to 153°C In the electrophotographic photoreceptor of the present invention, examples of the conductive support include metal pipes, metal plates, metal sheets, metal foils, conductive-treated polymer films, AI, etc. A polymer film provided with a metal vapor deposition layer, a polymer film or paper coated with a metal oxide such as SnO, a quaternary ammonium salt, or the like is used.

本発明の電子写真感光体において、導電性支持体上には
、感光層が設けられるが、感光層は単層構造のものでも
よく、又、電荷発生層と電荷輸送層とに機能分離された
積層構造のものでもよい。In the electrophotographic photoreceptor of the present invention, a photosensitive layer is provided on the conductive support, but the photosensitive layer may have a single layer structure, or may be functionally separated into a charge generation layer and a charge transport layer. It may also have a laminated structure.

感光層が単層構造の場合には、例えば、ポリビニルカル
バゾール等の公知の材料から構成された感光層中に上記
−投銭（Ｉ＞で示される化合物を増感材として含有させ
たもの、又は公知の電荷発生材を含む結着樹脂層中に上
記−投銭（Ｉ＞で示される化合物を電子輸送材として含
有させたものなどが挙げられる。When the photosensitive layer has a single layer structure, for example, a photosensitive layer made of a known material such as polyvinylcarbazole contains the compound represented by I> as a sensitizing material, or a known material. For example, a binder resin layer containing a charge generating material may contain a compound represented by I> as an electron transporting material.

一方、感光層が積層構造の場合において、電荷発生層は
、例えば、電荷発生材を導電性支持体−Ｆに蒸着して得
られたものでもよく、又、電荷発生材と結着樹脂とを主
成分とする塗布液を塗布することによって形成されたも
のでもよい。On the other hand, when the photosensitive layer has a laminated structure, the charge generation layer may be obtained by depositing a charge generation material on a conductive support -F, or may be obtained by depositing a charge generation material and a binder resin. It may be formed by applying a coating liquid as the main component.

電荷発生材及び結着樹脂としては、公知のものならば、
どのようなものでも使用できる。例えば、電荷発生材と
しては、ｔ　ｒ　ｉ　−３ｅなどの無機半導体、ポリビ
ニルカルバゾール等の有機半導体、ビスアゾ系化合物、
トリスアゾ系化合物、フタロシアニン類、ピリリウム化
合物、スクェアリウム化合物等の有機顔料が使用でき、
又、結着樹脂としては、ポリスチレン、シリコーン樹脂
、ポリカーボネート樹脂、アクリル樹脂、メタクリル樹
脂、ポリエステル、ビニル系重合体、セルロース類、ア
ルキッド樹脂等が使用できる。As the charge generating material and the binder resin, any known ones may be used.
You can use anything. For example, charge generating materials include inorganic semiconductors such as tri-3e, organic semiconductors such as polyvinylcarbazole, bisazo compounds,
Organic pigments such as trisazo compounds, phthalocyanines, pyrylium compounds, and squareium compounds can be used.
Further, as the binder resin, polystyrene, silicone resin, polycarbonate resin, acrylic resin, methacrylic resin, polyester, vinyl polymer, cellulose, alkyd resin, etc. can be used.

電荷発生層の膜厚は、Ｏ，ＯＳ〜１０ＩＪｍ程度に設定
される。The thickness of the charge generation layer is set to about O,OS to 10 IJm.

電荷発生層の上には電荷輸送層が形成される。A charge transport layer is formed on the charge generation layer.

この電荷輸送層は、上記−投銭（Ｉ＞で示される化合物
と結着樹脂とより構成されるもので市って、上記−投銭
（Ｉ）で示される化合物、結着樹脂及び適当な溶媒を主
成分とする塗布液を、アプリケータ、バーコータ、デイ
ツプコータ等により、電荷発生層上に塗布することによ
って形成される。This charge transport layer is composed of a compound represented by the above-mentioned -Isen (I) and a binder resin. It is formed by applying a coating liquid containing the main component onto the charge generation layer using an applicator, bar coater, dip coater, or the like.

この場合、上記−投銭（Ｉ＞で示される化合物と結着樹
脂との混合比は、１　：２０〜２０：１程度に設定され
る。In this case, the mixing ratio of the compound represented by -I> and the binder resin is set to about 1:20 to 20:1.

電荷輸送層に用いる結着樹脂としては、公知のものなら
ば、どのようなものでも使用できる。例えば、スチレン
−ブタジェン共重合体、ビニルトルエン−スチレン共重
合体、スチレン変性アルキッド樹脂、シリコーン変性ア
ルキッド樹脂、大豆油変性アルキッド樹脂、塩化ビニル
デンー塩化ビニル共重合体、ポリビニルブチラール、ニ
トロ化ポリスチレン、ポリメチルスチレン、ポリイソブ
チレン、ポリエステル、フェノール樹脂、ケトン樹脂、
ポリアミド、ポリカーボネート、ポリチオカーボネート
、ポリビニルハロアリレート、酢酸ビニル系樹脂、ポリ
スチレン、ポリビニルアクリレート、ポリスルホン、ポ
リメタクリレート等がめげられる。また、電荷輸送層に
電子供与性物質を添加してもよい。Any known binder resin can be used for the charge transport layer. For example, styrene-butadiene copolymer, vinyltoluene-styrene copolymer, styrene-modified alkyd resin, silicone-modified alkyd resin, soybean oil-modified alkyd resin, vinyldene chloride-vinyl chloride copolymer, polyvinyl butyral, nitrated polystyrene, polymethyl Styrene, polyisobutylene, polyester, phenolic resin, ketone resin,
Examples include polyamide, polycarbonate, polythiocarbonate, polyvinyl haloarylate, vinyl acetate resin, polystyrene, polyvinyl acrylate, polysulfone, polymethacrylate, and the like. Further, an electron donating substance may be added to the charge transport layer.

電荷輸送層の膜厚は、２〜１１０１ｒ程度に設定される
。The thickness of the charge transport layer is set to about 2 to 1101r.

なお、本発明の電子写真感光体においては、導電性支持
体の上に、障壁層を設けてもよい。障壁層は、導電性支
持体からの不必要な電荷の注入を阻止するために有効で
あり、画質を向上させる作用がおる。障壁層を構成する
材料としては、酸化アルミニウム等の金属酸化物あるい
はアクリル樹脂、フェノール樹脂、ポリエステル樹脂、
ポリウレタン等がめげられる。In addition, in the electrophotographic photoreceptor of the present invention, a barrier layer may be provided on the conductive support. The barrier layer is effective in preventing unnecessary charge injection from the conductive support, and has the effect of improving image quality. Materials constituting the barrier layer include metal oxides such as aluminum oxide, acrylic resins, phenolic resins, polyester resins,
Polyurethane etc. are damaged.

実施例 以下、本発明を実施例によって説明する。Example Hereinafter, the present invention will be explained by examples.

実施例１ 導電性基板上に、三方晶系セレン／ポリビニルカルバゾ
ール（三方晶系セレンニア容量％）からなる電荷発生層
（２，５Ｉｊｍ）を設け、その上に、例示化合物（３）
０．５　（ｊ及びビスフェノールＡポリカーボネート（
マクロロン５７０５）０．７５　ｇを塩化メチレン７ｔ
ｊに溶解した溶液を、湿潤時のギャップ５ミルで塗布し
、８０℃で１時間乾燥して、電子写真感光体を作成した
。この電子写真感光体について、静電複写紙試験装置（
ＳＰ４２８　、川口電機製作所ＩｔｉＪ製）を用いて＋
ａｏｏｖ及び−ａｏｏｖに帯電し、５ルツクスの白色光
を露光し、感度（ｄＶ／ｄｔ）を測定した。結果は次の
通りであった。Example 1 A charge generation layer (2,5 Ijm) made of trigonal selenium/polyvinylcarbazole (trigonal selenium capacity %) was provided on a conductive substrate, and exemplified compound (3)
0.5 (j and bisphenol A polycarbonate (
Macrolon 5705) 0.75 g to 7t of methylene chloride
A solution dissolved in J was applied with a wet gap of 5 mil, and dried at 80° C. for 1 hour to prepare an electrophotographic photoreceptor. Regarding this electrophotographic photoreceptor, an electrostatic copying paper tester (
SP428, manufactured by Kawaguchi Electric Seisakusho ItiJ)
It was charged to aoov and -aoov, exposed to 5 lux white light, and the sensitivity (dV/dt) was measured. The results were as follows.

帯電電位　　＋８００Ｖ　　　−８００Ｖ初期感度　　
　５３０ （Ｖ／５ｅｃ） 実施例２〜７ 例示化合物（３）の代わりに、例示化合物（５）、（７
）　、（１０）、（１１）、（１２）、及び（１５）を
用いた以外は、実施例１と同様にして電子写真感光体を
作成し、同様に感度を測定した。結果を第１表に示す。Charge potential +800V -800V Initial sensitivity
530 (V/5ec) Examples 2 to 7 Exemplary compound (5), (7
), (10), (11), (12), and (15) were used. Electrophotographic photoreceptors were prepared in the same manner as in Example 1, and the sensitivity was measured in the same manner. The results are shown in Table 1.

比較例１ 例示化合物（３）の代わりに２．４．７−ドリニトロフ
ルオレノン（丁ＮＦ）を用いた以外は、実施例１におけ
ると同様にして電子写真感光体を作成し、同様にして感
度を測定した。結果を第１表に示す。Comparative Example 1 An electrophotographic photoreceptor was prepared in the same manner as in Example 1, except that 2.4.7-dolinitrofluorenone (DinNF) was used in place of Exemplified Compound (3), and the sensitivity was determined in the same manner. was measured. The results are shown in Table 1.

以下余白 第１表 実施例８ 導電性基板上に、例示化合物（３）　０．５　ｇ、ポリ
ビニルカルバゾール０．７５　＝ｊを、塩化メチレン７
ｇに溶かした溶液を、湿潤時のギャップ５ミルで塗布し
、８０’Ｃで１時間乾燥して、電子写真感光体を作成し
た。これらの電子写真感光体について、静電複写紙試験
装＠　（ＳＰ４２８、川口電機製作所＜ｍ′ｔＡ＞を用
いて＋ａｏｏｖ及び−ａｏｏｖに帯電し、５ルツクスの
白色光を露光し、感度（ｄＶ／ｄＴ）を測定した。結果
は次の通りであった。Table 1 with blank space below Example 8 On a conductive substrate, 0.5 g of exemplified compound (3), 0.75 = j of polyvinylcarbazole, and 7 g of methylene chloride were added.
An electrophotographic photoreceptor was prepared by applying a solution dissolved in 100 g at a wet gap of 5 mil and drying at 80'C for 1 hour. These electrophotographic photoreceptors were charged to +aoov and -aoov using an electrostatic copying paper tester @ (SP428, Kawaguchi Electric Seisakusho <m'tA>), exposed to 5 lux white light, and the sensitivity (dV/ dT) was measured.The results were as follows.

帯！電位＋８００Ｖ　　　−８００Ｖ 初期感度　　４６５　　　１７７ （ｖ、”５ｅｃ） 実施例９〜１４ 例示化合物（３）の代わりに、例示化合物（５）、（旬
、（１０）、（１１）、（１２）、及び（１５）を用い
た以外は、実施例８と同様にして電子写真感光体を作成
し、同様に感度を測定した。結果を第２表に示す。band! Potential +800V -800V Initial sensitivity 465 177 (v, "5ec) Examples 9 to 14 In place of exemplified compound (3), exemplified compound (5), (10), (11), (12), and An electrophotographic photoreceptor was prepared in the same manner as in Example 8, except that (15) was used, and the sensitivity was measured in the same manner.The results are shown in Table 2.

比較例２ 例示化合物（３）の代わりに２．４．７−ドリニトロフ
ルオレノン（ＴＮｒ）を用いた以外は、実施例８におけ
ると同様にして電子写真感光体を作成し、同様にして感
度を測定した。結果を第２表に示す。Comparative Example 2 An electrophotographic photoreceptor was prepared in the same manner as in Example 8, except that 2.4.7-dolinitrofluorenone (TNr) was used instead of Exemplified Compound (3), and the sensitivity was adjusted in the same manner. It was measured. The results are shown in Table 2.

以下余白 第２表 発明の効果 上記実施例と比較例の比較からも明らかなように、本発
明において用いる上記−投銭（Ｉ＞で示される化合物は
、従来比較的滑れたものとして知られている丁ＮＦより
も優れた電子輸送性を示し、したがって、このものを用
いた電子写真感光体は、優れた電子写真特性を示す。特
に、積層型の電子写真感光体の電荷輸送層において電荷
輸送材として用いた場合には、優れた電子写真特性を示
す正帯電型の電子写真感光°体が得られる。Table 2 in the margin below Effects of the Invention As is clear from the comparison between the above Examples and Comparative Examples, the compound represented by I> used in the present invention is conventionally known to be relatively slippery. It exhibits better electron transport properties than DIN NF, and therefore, an electrophotographic photoreceptor using this material exhibits excellent electrophotographic properties.In particular, in the charge transport layer of a laminated electrophotographic photoreceptor, the charge transport material When used as an electrophotographic photoreceptor, a positively charged electrophotographic photoreceptor exhibiting excellent electrophotographic properties can be obtained.

手続補正書 （自発） 平成　１年　７月１９日 特許庁長官　　吉　１）文　毅　殿 １、事件の表示 昭和６３年　特許願　第２８７６１８号２、発明の名称 電子写真感光体 ３、補正をする者 事件との関係　特許出願人 住　所　　東京都港区赤坂３丁目３番５号名　称　　（
５４９）富士ゼロックス株式会社代表者　　小林陽太部 ４、代理人 住所　〒１０１ 東京都千代田区神田錦町１丁目８番５号６、補正の内容 Ｃ）「特許請求の範囲」を別紙の通り補正する。Procedural amendment (voluntary) July 19, 1999 Director General of the Japan Patent Office Yoshi 1) Moon Takeshi 1, Indication of the case 1987 Patent Application No. 287618 2, Name of the invention Electrophotographic photoreceptor 3, Person making the amendment Relationship to the incident Patent applicant address 3-3-5 Akasaka, Minato-ku, Tokyo Name (
549) Fuji Xerox Co., Ltd. Representative: Yotabe Kobayashi 4, Agent Address: 1-8-5-6, Kanda Nishiki-cho, Chiyoda-ku, Tokyo 101, Japan Contents of Amendment C) The "Scope of Claims" will be amended as shown in the attached sheet.

■　明細書第５頁下から第５行目から下から第４行目の
「アルール基」を「アリール基」に補正する Ｇ）同第１３頁第６行目の「塩化ビニルデン」を「塩化
ビニリデン」に補正する。■ Correct the "allyl group" in the fifth line from the bottom of the specification to "aryl group" on page 5 of the specification. Correct to “vinylidene”.

以上 明細書の 「特許請求の範囲」及び「発明の詳細な説明」［別紙］ ２、特許請求の範囲 （１）導電性支持体上に感光層を設けてなる電子写真感
光体において、該感光層が、電荷輸送材として、下記一
般式（Ｉ）で示される化合物を含有してなることを特徴
とする電子写真感光体。"Claims" and "Detailed Description of the Invention" [Attachment] 2. Claims (1) In an electrophotographic photoreceptor comprising a photosensitive layer provided on a conductive support, An electrophotographic photoreceptor characterized in that the layer contains a compound represented by the following general formula (I) as a charge transport material.

（式中、Ｒ１及びＲ２は、それぞれ水素原子、アルキル
基、アリール基、アルコキシカルボニル基、アリールオ
キシカルボニル基、ニトロ基、ハロゲン原子、アルキル
カルボニル基又はアリールカルボニル基を示し、Ｒ３は
置換されていてもよいアリール基又は含窒素複素環基を
示し、ｍは０又はｌを示し、ｎは０〜２を示す）(In the formula, R1 and R2 each represent a hydrogen atom, an alkyl group, an aryl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a nitro group, a halogen atom, an alkylcarbonyl group, or an arylcarbonyl group, and R3 is substituted. aryl group or nitrogen-containing heterocyclic group, m represents 0 or l, n represents 0 to 2)

Claims (1)

【特許請求の範囲】[Claims] （１）導電性支持体上に感光層を設けてなる電子写真感
光体において、該感光層が、電荷輸送材として、下記一
般式（ I ）で示される化合物を含有してなることを特
徴とする電子写真感光体。 ▲数式、化学式、表等があります▼（ I ） （式中、Ｒ＿１及びＲ＿２は、それぞれ水素原子、アル
キル基、アリール基、アルコキシカルボニル基、アリー
ルオキシカルボニル基、ニトロ基、ハロゲン原子、アル
キルカルボニル基又はアリールカルボニル基を示し、Ｒ
＿３は置換されていてもよいアルール基又は含窒素複素
環基を示し、ｍは０又は１を示し、ｎは０〜２を示す）(1) An electrophotographic photoreceptor comprising a photosensitive layer provided on a conductive support, characterized in that the photosensitive layer contains a compound represented by the following general formula (I) as a charge transport material. Electrophotographic photoreceptor. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, R_1 and R_2 are hydrogen atoms, alkyl groups, aryl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, nitro groups, halogen atoms, and alkylcarbonyl groups, respectively. or represents an arylcarbonyl group, R
_3 represents an optionally substituted allyl group or nitrogen-containing heterocyclic group, m represents 0 or 1, and n represents 0 to 2)
JP63287618A 1988-11-16 1988-11-16 Electrophotographic sensitive body Pending JPH02135361A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP63287618A JPH02135361A (en) 1988-11-16 1988-11-16 Electrophotographic sensitive body
US07/436,875 US5011757A (en) 1988-11-16 1989-11-15 Electrophotographic photoreceptor containing a fluorene derivative
US07/506,602 US5075487A (en) 1988-11-16 1990-04-10 Fluorene derivative

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP63287618A JPH02135361A (en) 1988-11-16 1988-11-16 Electrophotographic sensitive body

Publications (1)

Publication Number Publication Date
JPH02135361A true JPH02135361A (en) 1990-05-24

Family

ID=17719595

Family Applications (1)

Application Number Title Priority Date Filing Date
JP63287618A Pending JPH02135361A (en) 1988-11-16 1988-11-16 Electrophotographic sensitive body

Country Status (1)

Country Link
JP (1) JPH02135361A (en)

Cited By (115)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5807974A (en) * 1996-05-16 1998-09-15 Korea Institute Of Science And Technology Fluorene-based alternating copolymers for electroluminescence element and electroluminescence element using such copolymers as light emitting materials
US6207301B1 (en) 1996-08-21 2001-03-27 Sumitomo Chemical Company, Limited Polymer fluorescent substance and organic electroluminescence device
EP1138746A1 (en) 2000-03-31 2001-10-04 Sumitomo Chemical Company, Limited Polymeric fluorescent substance, production method therof, and polymer light-emitting device using the same
US6462356B1 (en) 1999-10-25 2002-10-08 Seiko Epson Corporation Light emitting device
US6512250B1 (en) 1999-06-10 2003-01-28 Seiko Epson Corporation Light-emitting device
US6587620B2 (en) 2000-06-16 2003-07-01 Seiko Epson Corporation Surface emitting device
JP2003197881A (en) * 2001-12-27 2003-07-11 Seiko Epson Corp Semiconductor integrated circuit, manufacturing method for the semiconductor integrated circuit, semiconductor element member, electrooptic device, and electronic equipment
US6704335B1 (en) 1998-12-17 2004-03-09 Seiko Epson Corporation Light-emitting device
US6727646B1 (en) 1999-03-23 2004-04-27 Seiko Epson Corporation Light-emitting device
US6734621B2 (en) 2001-09-10 2004-05-11 Seiko Epson Corporation Light emitting device having magnetized cathode and anode
US6737802B2 (en) 2000-08-11 2004-05-18 Seiko Epson Corporation Light-emitting device
US6791115B2 (en) 2001-03-09 2004-09-14 Seiko Epson Corporation Light emitting device, display device and electronic instrument
US6791660B1 (en) 2002-02-12 2004-09-14 Seiko Epson Corporation Method for manufacturing electrooptical device and apparatus for manufacturing the same, electrooptical device and electronic appliances
US6795463B2 (en) 2000-03-01 2004-09-21 Seiko Epson Corporation Light -emitting device
US6830832B2 (en) 2001-11-09 2004-12-14 Sumitomo Chemical Company, Limited Polymer compound and polymer light-emitting device using the same
WO2004108417A1 (en) 2003-06-04 2004-12-16 Mimaki Engineering Co.,Ltd. Ink jet printer using uv ink
US6858518B2 (en) 2001-12-28 2005-02-22 Seiko Epson Corporation Method for manufacturing semiconductor integrated circuit
US6870182B2 (en) 2001-11-06 2005-03-22 Seiko Epson Corporation Organic semiconductor device
US6926973B2 (en) 2001-12-19 2005-08-09 Sumitomo Chemical Company, Limited Copolymer, polymer composition and polymer light-emitting device
US6943050B2 (en) 2002-07-11 2005-09-13 Seiko Epson Corporation Method for making semiconductor device, semiconductor element composite, electro-optical apparatus, and electronic system
US6982436B2 (en) 2002-07-23 2006-01-03 Seiko Epson Corporation Light-emitting device, method of manufacturing the same, and electronic apparatus
US6985275B2 (en) 2001-11-06 2006-01-10 Seiko Epson Corporation Electro-optical device, film member, laminated film, low refractivity film, laminated multilayer film and electronic appliances
US6995893B2 (en) 2002-05-10 2006-02-07 Seiko Epson Corporation Electro-optical device, method for manufacturing electro-optical device, apparatus for manufacturing electro-optical device, and electronic apparatus
US7025647B2 (en) 2001-10-30 2006-04-11 Seiko Epson Corporation Method for manufacturing laminated film, electro-optical device, method for manufacturing electro-optical device, organic electroluminescence device, and electronic appliances
US7042154B2 (en) 2002-06-07 2006-05-09 Seiko Epson Corporation Organic electroluminescent device having wiring lines under the partition walls and electronic apparatus using the same
US7132789B2 (en) 2003-08-18 2006-11-07 Seiko Epson Corporation Organic EL device, method of manufacturing the same and electronic apparatus
US7138764B2 (en) 2001-10-24 2006-11-21 Seiko Epson Corporation Light-emitting device and electronic instrument
US7148508B2 (en) 2002-03-20 2006-12-12 Seiko Epson Corporation Wiring substrate, electronic device, electro-optical device, and electronic apparatus
US7180924B2 (en) 2002-05-30 2007-02-20 Seiko Epson Corporation Semiconductor apparatus and a semiconductor unit, the semiconductor unit including a functional layer including a semiconductor element, and a highly conductive layer
US7211838B2 (en) 2001-12-27 2007-05-01 Seiko Epson Corporation Apparatus and method for manufacturing electro-optical devices
US7242140B2 (en) 2002-05-10 2007-07-10 Seiko Epson Corporation Light emitting apparatus including resin banks and electronic device having same
US7280933B2 (en) 2004-01-15 2007-10-09 Seiko Epson Corporation Method and apparatus for forming a pattern, device and electronic apparatus
WO2008016067A1 (en) 2006-08-01 2008-02-07 Sumitomo Chemical Company, Limited Polymer compound and polymer light-emitting device
WO2008016091A1 (en) 2006-07-31 2008-02-07 Sumitomo Chemical Company, Limited Polymer compound and polymer light-emitting device using the same
WO2008026649A1 (en) 2006-08-30 2008-03-06 Sumitomo Chemical Company, Limited Organic electroluminescence element
WO2008032843A1 (en) 2006-09-14 2008-03-20 Sumitomo Chemical Company, Limited Organic electroluminescent device
WO2008032720A1 (en) 2006-09-13 2008-03-20 Sumitomo Chemical Company, Limited Polymer compound and polymer light-emitting device
WO2008038747A1 (en) 2006-09-25 2008-04-03 Sumitomo Chemical Company, Limited Polymer compound and polymer light-emitting device using the same
WO2008093821A1 (en) 2007-02-02 2008-08-07 Sumitomo Chemical Company, Limited Polymer light-emitting device, polymer compound, composition, liquid composition, and conductive thin film
WO2008096737A1 (en) 2007-02-06 2008-08-14 Sumitomo Chemical Company, Limited Indole compound-containing composition and light-emitting device using the composition
WO2008096735A1 (en) 2007-02-06 2008-08-14 Sumitomo Chemical Company, Limited Composition containing pyrimidine compound and luminescent element employing the composition
DE112006002668T5 (en) 2005-10-07 2008-08-14 Sumitomo Chemical Company, Ltd. Copolymer and polymeric light-emitting device using the same
WO2008096736A1 (en) 2007-02-06 2008-08-14 Sumitomo Chemical Company, Limited Benzotriazole compound-containing composition and light-emitting device using the composition
WO2008096739A1 (en) 2007-02-06 2008-08-14 Sumitomo Chemical Company, Limited Benzimidazole compound-containing composition and light-emitting device using the composition
WO2008096742A1 (en) 2007-02-06 2008-08-14 Sumitomo Chemical Company, Limited Indazole compound-containing composition and light-emitting device using the composition
DE112006002642T5 (en) 2005-10-07 2008-08-21 Sumitomo Chemical Company, Ltd. Polymer and polymeric luminescent element using this
WO2008111658A1 (en) 2007-03-09 2008-09-18 Sumitomo Chemical Company, Limited Polymer compound and composition containing the same
DE112006002998T5 (en) 2005-11-18 2008-09-18 Sumitomo Chemical Co., Ltd. Polymer compound and polymer-containing light-emitting device using the same
DE112006003090T5 (en) 2005-11-11 2008-09-25 Sumitomo Chemical Co. Ltd. Conjugated polymer compound and polymeric light-emitting device using them
DE112006002147T5 (en) 2005-08-12 2008-10-23 Sumitomo Chemical Co., Ltd. Polymer compound and polymeric light-emitting device using these
EP1986472A2 (en) 2001-09-12 2008-10-29 Seiko Epson Corporation Method for patterning, method for forming film, patterning apparatus, film formation apparatus, electro-optic apparatus and method for manufacturing the same, electronic equipment, and electronic apparatus and method for manufacturing the same
DE112006003570T5 (en) 2005-12-28 2008-11-06 Sumitomo Chemical Co., Ltd. block copolymer
US7449833B2 (en) 2003-11-07 2008-11-11 Seiko Epson Corporation Light-emitting device having openings in electrode
WO2008136492A1 (en) 2007-04-27 2008-11-13 Sumitomo Chemical Company, Limited Pyrene polymer and luminescent element made with the same
DE112007000169T5 (en) 2006-01-16 2008-11-27 Sumitomo Chemical Co. Ltd. Polymer compound and polymer-based light-emitting device using the same
WO2008149829A1 (en) 2007-05-30 2008-12-11 Sumitomo Chemical Company, Limited Organic electroluminescent device and display using the device
DE112007000426T5 (en) 2006-02-22 2009-01-02 Sumation Co. Ltd. Metal complex, polymer compound and device containing it
WO2009008543A1 (en) 2007-07-12 2009-01-15 Sumitomo Chemical Company, Limited Method for manufacturing organic light-emitting device
WO2009017056A1 (en) 2007-07-31 2009-02-05 Sumitomo Chemical Company, Limited Compound, method for producing the same, ink composition using the compound, thin film, organic transistor, and organic electroluminescent device
WO2009048164A1 (en) 2007-10-10 2009-04-16 Sumitomo Chemical Company, Limited Polymer compound and polymer light-emitting device using the same
DE112007001294T5 (en) 2006-05-31 2009-04-23 Sumitomo Chemical Co., Ltd. Polymer compound and polymeric light-emitting device
WO2009069476A1 (en) 2007-11-30 2009-06-04 Sumitomo Chemical Company, Limited Electronic device, display apparatus and method for manufacturing electronic device
WO2009069820A1 (en) 2007-11-29 2009-06-04 Sumitomo Chemical Company, Limited Organic electroluminescent device and method for manufacturing the same
EP2067808A1 (en) 2001-12-07 2009-06-10 Sumitomo Chemical Company, Limited New polymer and polymer light-emitting device using the same
WO2009084590A1 (en) 2007-12-28 2009-07-09 Sumitomo Chemical Company, Limited Polymer light-emitting device, method for manufacturing the same and polymer light-emitting display device
WO2009110642A1 (en) 2008-03-07 2009-09-11 住友化学株式会社 Layered structure
EP2107076A1 (en) 2002-03-15 2009-10-07 Sumitomo Chemical Company, Limited Conjugated polymer comprising dibenzothiophene- or dibenzofuran-units and their use in polymer LEDs
WO2009131254A1 (en) 2008-04-25 2009-10-29 住友化学株式会社 Composition containing nitrogenous heterocyclic compounds
WO2009131255A1 (en) 2008-04-25 2009-10-29 住友化学株式会社 Polymeric compound having residue of nitrogenated heterocyclic compound
WO2009148103A1 (en) 2008-06-05 2009-12-10 住友化学株式会社 Polymer compound and organic transistor using the polymer compound
WO2009151144A1 (en) 2008-06-13 2009-12-17 住友化学株式会社 Copolymer and polymer light-emitting element using the same
WO2009157429A1 (en) 2008-06-23 2009-12-30 住友化学株式会社 Phosphorescence-emitting composition, and light-emitting element utilizing the composition
WO2009157427A1 (en) 2008-06-23 2009-12-30 住友化学株式会社 Composition and light-emitting element comprising the same
WO2009157426A1 (en) 2008-06-23 2009-12-30 住友化学株式会社 Composition and light-emitting element using the composition
WO2009157428A1 (en) 2008-06-23 2009-12-30 住友化学株式会社 Phosphorescent light-emitting composition and light-emitting element comprising the composition
US7656084B2 (en) 2004-03-03 2010-02-02 Seiko Epson Corporation Method of producing laminated type organic electroluminescent element and display apparatus
WO2010013725A1 (en) 2008-07-30 2010-02-04 住友化学株式会社 Laminated structure, method for producing same, and electronic element comprising same
WO2010013827A1 (en) 2008-07-29 2010-02-04 住友化学株式会社 Composition comprising phosphorescence emitting compound, and light emitting element using the composition
WO2010026972A1 (en) 2008-09-03 2010-03-11 住友化学株式会社 Polymer compound and polymer light-emitting element utilizing same
US7679082B2 (en) 2004-11-10 2010-03-16 Qidan Ling Multi-functional copolymers comprising rare earth metal complexes and devices thereof
WO2010041559A1 (en) 2008-10-06 2010-04-15 住友化学株式会社 Polymer compound containing nitrogen-containing heterocyclic structure, and composition, solution, thin film and polymer light-emitting element each containing same
US7754274B2 (en) 2003-11-17 2010-07-13 Seiko Epson Corporation Mask and method for manufacturing the same, method for manufacturing display, method for manufacturing organic electroluminescent display, organic electroluminescent device, and electronic device
WO2010087510A1 (en) 2009-01-29 2010-08-05 住友化学株式会社 High-molecular compound and light-emitting element using same
EP2221354A2 (en) 2001-04-27 2010-08-25 Sumitomo Chemical Company, Limited New polymeric fluorescent substance and polymer light-emitting device using the same
EP2236561A1 (en) 2005-05-20 2010-10-06 Sumitomo Chemical Company, Limited Polymer composition and polymer light-emitting device using same
WO2010123131A1 (en) 2009-04-23 2010-10-28 住友化学株式会社 Metal complex having aromatic ligand that contains nitrogen atom
EP2258808A2 (en) 2001-03-27 2010-12-08 Sumitomo Chemical Company, Limited Polymeric light emitting substance and polymer light emitting device using the same
EP2277979A1 (en) 1999-04-09 2011-01-26 Sumitomo Chemical Company, Limited Polymeric fluorescent substance and polymer light emitting device
EP2302014A1 (en) 2000-03-16 2011-03-30 Sumitomo Chemical Company, Limited Polymeric fluorescent substance, polymeric fluorescent substance solution and polymer light-emitting device having low contents of poor solvents
WO2011040388A1 (en) 2009-09-30 2011-04-07 住友化学株式会社 Laminated structure, polymer, electroluminescent element, and photoelectric conversion element
WO2011049241A1 (en) 2009-10-22 2011-04-28 住友化学株式会社 Organic electroluminescent element
DE112009001538T5 (en) 2008-06-23 2011-05-05 Sumation Co. Ltd. Composition and produced using the composition light emitting element
EP2325225A1 (en) 2002-10-30 2011-05-25 Sumitomo Chemical Company, Limited Complex aryl copolymer compounds and polymer light emitting devices made by using the same
EP2333006A1 (en) 2001-04-27 2011-06-15 Sumitomo Chemical Company, Limited Block copolymer and polymeric luminescent element
WO2011087058A1 (en) 2010-01-15 2011-07-21 住友化学株式会社 Polymer light emitting element
WO2011093428A1 (en) 2010-01-28 2011-08-04 住友化学株式会社 Polymer compound and light-emitting device using same
WO2011093411A1 (en) 2010-01-29 2011-08-04 住友化学株式会社 Polymer compound, method for producing same, and light-emitting element using the polymer compound
WO2011093460A1 (en) 2010-01-29 2011-08-04 住友化学株式会社 Light-emitting material, ink composition, thin film, light-emitting element, and method for manufacturing a light-emitting element
WO2011105622A1 (en) 2010-02-25 2011-09-01 住友化学株式会社 Fluoranthene polymeric compound
WO2011132698A1 (en) 2010-04-20 2011-10-27 住友化学株式会社 Organic light-emitting element
EP2432300A1 (en) 2005-11-30 2012-03-21 Sumitomo Chemical Co., Ltd White organic electroluminescent device
WO2012124770A1 (en) 2011-03-17 2012-09-20 住友化学株式会社 Metal complex compositions and mixture thereof
DE112010004188T5 (en) 2009-10-28 2012-11-22 Sumitomo Chemical Co., Ltd. Metal complex with multidentate ligand
DE112011100845T5 (en) 2010-03-10 2013-01-24 Hiroshima University Thin film and used in the same compound
WO2013146806A1 (en) 2012-03-27 2013-10-03 住友化学株式会社 Polymer compound and light emitting element using same
WO2013151130A1 (en) 2012-04-06 2013-10-10 住友化学株式会社 Organic electroluminescence element and method for manufacturing same
WO2013151170A1 (en) 2012-04-06 2013-10-10 住友化学株式会社 Application system, and method for producing light-emitting device
WO2013151129A1 (en) 2012-04-06 2013-10-10 住友化学株式会社 Organic electroluminescent element and method of manufacturing same
WO2014061493A1 (en) 2012-10-15 2014-04-24 住友化学株式会社 Method for manufacturing electronic device
US9184388B2 (en) 2010-07-29 2015-11-10 Sumitomo Chemical Company, Limited Layered structure, electronic device using same, aromatic compound, and method for manufacturing said compound
US9837612B2 (en) 2010-12-21 2017-12-05 Sumitomo Chemical Company, Limted Polymer compound and light-emitting device using same
WO2018146950A1 (en) 2017-02-09 2018-08-16 住友化学株式会社 Method for manufacturing organic electronic device
WO2019078085A1 (en) 2017-10-19 2019-04-25 住友化学株式会社 Organic electronic device manufacturing method
WO2019131145A1 (en) 2017-12-26 2019-07-04 住友化学株式会社 Method for producing electronic device, and electronic device
WO2020039991A1 (en) 2018-08-21 2020-02-27 住友化学株式会社 Method for manufacturing electronic device

Cited By (148)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5807974A (en) * 1996-05-16 1998-09-15 Korea Institute Of Science And Technology Fluorene-based alternating copolymers for electroluminescence element and electroluminescence element using such copolymers as light emitting materials
US6207301B1 (en) 1996-08-21 2001-03-27 Sumitomo Chemical Company, Limited Polymer fluorescent substance and organic electroluminescence device
US6704335B1 (en) 1998-12-17 2004-03-09 Seiko Epson Corporation Light-emitting device
US6727646B1 (en) 1999-03-23 2004-04-27 Seiko Epson Corporation Light-emitting device
EP2292717A1 (en) 1999-04-09 2011-03-09 Sumitomo Chemical Company, Limited Polymeric fluorescent substance and polymer light emitting device
EP2280583A1 (en) 1999-04-09 2011-02-02 Sumitomo Chemical Company, Limited Polymeric fluorescent substance and polymer light emitting device
EP2277979A1 (en) 1999-04-09 2011-01-26 Sumitomo Chemical Company, Limited Polymeric fluorescent substance and polymer light emitting device
EP2280584A1 (en) 1999-04-09 2011-02-02 Sumitomo Chemical Company, Limited Polymeric fluorescent substance and polymer light emitting device
US6512250B1 (en) 1999-06-10 2003-01-28 Seiko Epson Corporation Light-emitting device
US6462356B1 (en) 1999-10-25 2002-10-08 Seiko Epson Corporation Light emitting device
US6795463B2 (en) 2000-03-01 2004-09-21 Seiko Epson Corporation Light -emitting device
EP2302014A1 (en) 2000-03-16 2011-03-30 Sumitomo Chemical Company, Limited Polymeric fluorescent substance, polymeric fluorescent substance solution and polymer light-emitting device having low contents of poor solvents
EP2308944A1 (en) 2000-03-16 2011-04-13 Sumitomo Chemical Company, Limited Polymeric fluorescent material, solution of this polymeric fluorescent material, and luminescent polymer device containing this material
EP2305773A1 (en) 2000-03-16 2011-04-06 Sumitomo Chemical Company, Limited Polymeric fluorescent substance, polymeric fluorescent substance solution and polymer light-emitting device having low water contents
EP1138746A1 (en) 2000-03-31 2001-10-04 Sumitomo Chemical Company, Limited Polymeric fluorescent substance, production method therof, and polymer light-emitting device using the same
US6587620B2 (en) 2000-06-16 2003-07-01 Seiko Epson Corporation Surface emitting device
US6737802B2 (en) 2000-08-11 2004-05-18 Seiko Epson Corporation Light-emitting device
US6791115B2 (en) 2001-03-09 2004-09-14 Seiko Epson Corporation Light emitting device, display device and electronic instrument
EP2258806A2 (en) 2001-03-27 2010-12-08 Sumitomo Chemical Company, Limited Polymeric light emitting substance and polymer light emitting device using the same
EP2258807A2 (en) 2001-03-27 2010-12-08 Sumitomo Chemical Company, Limited Polymeric light emitting substance and polymer light emitting device using the same
EP2258805A2 (en) 2001-03-27 2010-12-08 Sumitomo Chemical Company, Limited Polymeric light emitting substance and polymer light emitting device using the same
EP2258808A2 (en) 2001-03-27 2010-12-08 Sumitomo Chemical Company, Limited Polymeric light emitting substance and polymer light emitting device using the same
EP2258809A2 (en) 2001-03-27 2010-12-08 Sumitomo Chemical Company, Limited Polymeric light emitting substance and polymer light emitting device using the same
EP2264124A1 (en) 2001-04-27 2010-12-22 Sumitomo Chemical Company, Limited Polymeric fluorescent substance and polymer light-emitting device using the same
EP2221353A2 (en) 2001-04-27 2010-08-25 Sumitomo Chemical Company, Limited New polymeric fluorescent substance and polymer light-emitting device using the same
EP2221354A2 (en) 2001-04-27 2010-08-25 Sumitomo Chemical Company, Limited New polymeric fluorescent substance and polymer light-emitting device using the same
EP2333006A1 (en) 2001-04-27 2011-06-15 Sumitomo Chemical Company, Limited Block copolymer and polymeric luminescent element
EP2333005A1 (en) 2001-04-27 2011-06-15 Sumitomo Chemical Company, Limited Block copolymer and polymeric luminescent element
US6734621B2 (en) 2001-09-10 2004-05-11 Seiko Epson Corporation Light emitting device having magnetized cathode and anode
EP1986472A2 (en) 2001-09-12 2008-10-29 Seiko Epson Corporation Method for patterning, method for forming film, patterning apparatus, film formation apparatus, electro-optic apparatus and method for manufacturing the same, electronic equipment, and electronic apparatus and method for manufacturing the same
US7138764B2 (en) 2001-10-24 2006-11-21 Seiko Epson Corporation Light-emitting device and electronic instrument
US7025647B2 (en) 2001-10-30 2006-04-11 Seiko Epson Corporation Method for manufacturing laminated film, electro-optical device, method for manufacturing electro-optical device, organic electroluminescence device, and electronic appliances
US6870182B2 (en) 2001-11-06 2005-03-22 Seiko Epson Corporation Organic semiconductor device
US6985275B2 (en) 2001-11-06 2006-01-10 Seiko Epson Corporation Electro-optical device, film member, laminated film, low refractivity film, laminated multilayer film and electronic appliances
US7362515B2 (en) 2001-11-06 2008-04-22 Seiko Epson Corporation Electro-optical device, film member, laminated film, low refractivity film, laminated multilayer film and electronic appliances
US6830832B2 (en) 2001-11-09 2004-12-14 Sumitomo Chemical Company, Limited Polymer compound and polymer light-emitting device using the same
EP2067808A1 (en) 2001-12-07 2009-06-10 Sumitomo Chemical Company, Limited New polymer and polymer light-emitting device using the same
EP2067807A1 (en) 2001-12-07 2009-06-10 Sumitomo Chemical Company, Limited New polymer and polymer light-emitting device using the same
EP2033979A1 (en) 2001-12-19 2009-03-11 Sumitomo Chemical Company, Limited Copolymer or polymer composition and polymer light-emitting device
US6926973B2 (en) 2001-12-19 2005-08-09 Sumitomo Chemical Company, Limited Copolymer, polymer composition and polymer light-emitting device
US7244662B2 (en) 2001-12-27 2007-07-17 Seiko Epson Corporation Method for manufacturing semiconductor integrated circuit
JP2003197881A (en) * 2001-12-27 2003-07-11 Seiko Epson Corp Semiconductor integrated circuit, manufacturing method for the semiconductor integrated circuit, semiconductor element member, electrooptic device, and electronic equipment
US7714328B2 (en) 2001-12-27 2010-05-11 Seiko Epson Corporation Apparatus and method for manufacturing electro-optical devices
US7211838B2 (en) 2001-12-27 2007-05-01 Seiko Epson Corporation Apparatus and method for manufacturing electro-optical devices
US6858518B2 (en) 2001-12-28 2005-02-22 Seiko Epson Corporation Method for manufacturing semiconductor integrated circuit
US7317281B2 (en) 2002-02-12 2008-01-08 Seiko Epson Corporation Method for manufacturing electrooptical device and apparatus for manufacturing the same, electrooptical device and electronic appliances
US6791660B1 (en) 2002-02-12 2004-09-14 Seiko Epson Corporation Method for manufacturing electrooptical device and apparatus for manufacturing the same, electrooptical device and electronic appliances
EP2107076A1 (en) 2002-03-15 2009-10-07 Sumitomo Chemical Company, Limited Conjugated polymer comprising dibenzothiophene- or dibenzofuran-units and their use in polymer LEDs
US7696519B2 (en) 2002-03-20 2010-04-13 Seiko Epson Corporation Wiring substrate, electronic device, electro-optical device, and electronic apparatus
US7148508B2 (en) 2002-03-20 2006-12-12 Seiko Epson Corporation Wiring substrate, electronic device, electro-optical device, and electronic apparatus
US7529102B2 (en) 2002-03-20 2009-05-05 Seiko Epson Corporation Wiring substrate, electronic device, electro-optical device, and electronic apparatus
US7710027B2 (en) 2002-05-10 2010-05-04 Seiko Epson Corporation Light emitting apparatus including resin banks and electronic device having same
US7242140B2 (en) 2002-05-10 2007-07-10 Seiko Epson Corporation Light emitting apparatus including resin banks and electronic device having same
US6995893B2 (en) 2002-05-10 2006-02-07 Seiko Epson Corporation Electro-optical device, method for manufacturing electro-optical device, apparatus for manufacturing electro-optical device, and electronic apparatus
US7180924B2 (en) 2002-05-30 2007-02-20 Seiko Epson Corporation Semiconductor apparatus and a semiconductor unit, the semiconductor unit including a functional layer including a semiconductor element, and a highly conductive layer
US7042154B2 (en) 2002-06-07 2006-05-09 Seiko Epson Corporation Organic electroluminescent device having wiring lines under the partition walls and electronic apparatus using the same
US6943050B2 (en) 2002-07-11 2005-09-13 Seiko Epson Corporation Method for making semiconductor device, semiconductor element composite, electro-optical apparatus, and electronic system
US6982436B2 (en) 2002-07-23 2006-01-03 Seiko Epson Corporation Light-emitting device, method of manufacturing the same, and electronic apparatus
US7122845B2 (en) 2002-07-23 2006-10-17 Seiko Epson Corporation Light-emitting device, method of manufacturing the same, and electronic apparatus
EP2325226A1 (en) 2002-10-30 2011-05-25 Sumitomo Chemical Company, Limited Complex aryl copolymer compounds and polymer light emitting devices made by using the same
EP2325225A1 (en) 2002-10-30 2011-05-25 Sumitomo Chemical Company, Limited Complex aryl copolymer compounds and polymer light emitting devices made by using the same
EP2325224A1 (en) 2002-10-30 2011-05-25 Sumitomo Chemical Company, Limited Aryl copolymer compounds and polymer light emitting devices made by using the same
EP2325223A1 (en) 2002-10-30 2011-05-25 Sumitomo Chemical Company, Limited Complex aryl copolymer compounds and polymer light emitting devices made by using the same
WO2004108417A1 (en) 2003-06-04 2004-12-16 Mimaki Engineering Co.,Ltd. Ink jet printer using uv ink
US7132789B2 (en) 2003-08-18 2006-11-07 Seiko Epson Corporation Organic EL device, method of manufacturing the same and electronic apparatus
US7868543B2 (en) 2003-11-07 2011-01-11 Seiko Epson Corporation Light-emitting device having openings in electrode
US7449833B2 (en) 2003-11-07 2008-11-11 Seiko Epson Corporation Light-emitting device having openings in electrode
US7754274B2 (en) 2003-11-17 2010-07-13 Seiko Epson Corporation Mask and method for manufacturing the same, method for manufacturing display, method for manufacturing organic electroluminescent display, organic electroluminescent device, and electronic device
US7280933B2 (en) 2004-01-15 2007-10-09 Seiko Epson Corporation Method and apparatus for forming a pattern, device and electronic apparatus
US7656084B2 (en) 2004-03-03 2010-02-02 Seiko Epson Corporation Method of producing laminated type organic electroluminescent element and display apparatus
US7679082B2 (en) 2004-11-10 2010-03-16 Qidan Ling Multi-functional copolymers comprising rare earth metal complexes and devices thereof
EP2236561A1 (en) 2005-05-20 2010-10-06 Sumitomo Chemical Company, Limited Polymer composition and polymer light-emitting device using same
EP2960299A1 (en) 2005-05-20 2015-12-30 Sumitomo Chemical Co., Ltd. Polymer composition and polymer light-emitting device using the same
DE112006002147T5 (en) 2005-08-12 2008-10-23 Sumitomo Chemical Co., Ltd. Polymer compound and polymeric light-emitting device using these
DE112006002668T5 (en) 2005-10-07 2008-08-14 Sumitomo Chemical Company, Ltd. Copolymer and polymeric light-emitting device using the same
DE112006002642T5 (en) 2005-10-07 2008-08-21 Sumitomo Chemical Company, Ltd. Polymer and polymeric luminescent element using this
DE112006003090T5 (en) 2005-11-11 2008-09-25 Sumitomo Chemical Co. Ltd. Conjugated polymer compound and polymeric light-emitting device using them
DE112006002998T5 (en) 2005-11-18 2008-09-18 Sumitomo Chemical Co., Ltd. Polymer compound and polymer-containing light-emitting device using the same
EP2432300A1 (en) 2005-11-30 2012-03-21 Sumitomo Chemical Co., Ltd White organic electroluminescent device
DE112006003570T5 (en) 2005-12-28 2008-11-06 Sumitomo Chemical Co., Ltd. block copolymer
DE112007000169T5 (en) 2006-01-16 2008-11-27 Sumitomo Chemical Co. Ltd. Polymer compound and polymer-based light-emitting device using the same
DE112007000426T5 (en) 2006-02-22 2009-01-02 Sumation Co. Ltd. Metal complex, polymer compound and device containing it
DE112007001294T5 (en) 2006-05-31 2009-04-23 Sumitomo Chemical Co., Ltd. Polymer compound and polymeric light-emitting device
WO2008016091A1 (en) 2006-07-31 2008-02-07 Sumitomo Chemical Company, Limited Polymer compound and polymer light-emitting device using the same
WO2008016067A1 (en) 2006-08-01 2008-02-07 Sumitomo Chemical Company, Limited Polymer compound and polymer light-emitting device
WO2008026649A1 (en) 2006-08-30 2008-03-06 Sumitomo Chemical Company, Limited Organic electroluminescence element
WO2008032720A1 (en) 2006-09-13 2008-03-20 Sumitomo Chemical Company, Limited Polymer compound and polymer light-emitting device
WO2008032843A1 (en) 2006-09-14 2008-03-20 Sumitomo Chemical Company, Limited Organic electroluminescent device
WO2008038747A1 (en) 2006-09-25 2008-04-03 Sumitomo Chemical Company, Limited Polymer compound and polymer light-emitting device using the same
WO2008093821A1 (en) 2007-02-02 2008-08-07 Sumitomo Chemical Company, Limited Polymer light-emitting device, polymer compound, composition, liquid composition, and conductive thin film
EP2471834A1 (en) 2007-02-02 2012-07-04 Sumitomo Chemical Co., Ltd. New polymer, composition, liquid composition, and conductive thin film
EP2471833A1 (en) 2007-02-02 2012-07-04 Sumitomo Chemical Co., Ltd. Polymer, composition, liquid composition, and conductive thin film
WO2008096735A1 (en) 2007-02-06 2008-08-14 Sumitomo Chemical Company, Limited Composition containing pyrimidine compound and luminescent element employing the composition
WO2008096742A1 (en) 2007-02-06 2008-08-14 Sumitomo Chemical Company, Limited Indazole compound-containing composition and light-emitting device using the composition
WO2008096739A1 (en) 2007-02-06 2008-08-14 Sumitomo Chemical Company, Limited Benzimidazole compound-containing composition and light-emitting device using the composition
WO2008096736A1 (en) 2007-02-06 2008-08-14 Sumitomo Chemical Company, Limited Benzotriazole compound-containing composition and light-emitting device using the composition
EP2479236A1 (en) 2007-02-06 2012-07-25 Sumitomo Chemical Co., Ltd. Indazole compound-containing composition and light-emitting device using the composition
WO2008096737A1 (en) 2007-02-06 2008-08-14 Sumitomo Chemical Company, Limited Indole compound-containing composition and light-emitting device using the composition
EP2479235A1 (en) 2007-02-06 2012-07-25 Sumitomo Chemical Co., Ltd Indole compound-containing composition and light-emitting device using the composition
WO2008111658A1 (en) 2007-03-09 2008-09-18 Sumitomo Chemical Company, Limited Polymer compound and composition containing the same
WO2008136492A1 (en) 2007-04-27 2008-11-13 Sumitomo Chemical Company, Limited Pyrene polymer and luminescent element made with the same
WO2008149829A1 (en) 2007-05-30 2008-12-11 Sumitomo Chemical Company, Limited Organic electroluminescent device and display using the device
WO2009008543A1 (en) 2007-07-12 2009-01-15 Sumitomo Chemical Company, Limited Method for manufacturing organic light-emitting device
WO2009017056A1 (en) 2007-07-31 2009-02-05 Sumitomo Chemical Company, Limited Compound, method for producing the same, ink composition using the compound, thin film, organic transistor, and organic electroluminescent device
WO2009048164A1 (en) 2007-10-10 2009-04-16 Sumitomo Chemical Company, Limited Polymer compound and polymer light-emitting device using the same
WO2009069820A1 (en) 2007-11-29 2009-06-04 Sumitomo Chemical Company, Limited Organic electroluminescent device and method for manufacturing the same
WO2009069476A1 (en) 2007-11-30 2009-06-04 Sumitomo Chemical Company, Limited Electronic device, display apparatus and method for manufacturing electronic device
WO2009084590A1 (en) 2007-12-28 2009-07-09 Sumitomo Chemical Company, Limited Polymer light-emitting device, method for manufacturing the same and polymer light-emitting display device
WO2009110642A1 (en) 2008-03-07 2009-09-11 住友化学株式会社 Layered structure
EP2846374A1 (en) 2008-03-07 2015-03-11 Sumitomo Chemical Company Limited Layered structure
WO2009131254A1 (en) 2008-04-25 2009-10-29 住友化学株式会社 Composition containing nitrogenous heterocyclic compounds
WO2009131255A1 (en) 2008-04-25 2009-10-29 住友化学株式会社 Polymeric compound having residue of nitrogenated heterocyclic compound
WO2009148103A1 (en) 2008-06-05 2009-12-10 住友化学株式会社 Polymer compound and organic transistor using the polymer compound
WO2009151144A1 (en) 2008-06-13 2009-12-17 住友化学株式会社 Copolymer and polymer light-emitting element using the same
WO2009157426A1 (en) 2008-06-23 2009-12-30 住友化学株式会社 Composition and light-emitting element using the composition
DE112009001538T5 (en) 2008-06-23 2011-05-05 Sumation Co. Ltd. Composition and produced using the composition light emitting element
WO2009157428A1 (en) 2008-06-23 2009-12-30 住友化学株式会社 Phosphorescent light-emitting composition and light-emitting element comprising the composition
WO2009157427A1 (en) 2008-06-23 2009-12-30 住友化学株式会社 Composition and light-emitting element comprising the same
WO2009157429A1 (en) 2008-06-23 2009-12-30 住友化学株式会社 Phosphorescence-emitting composition, and light-emitting element utilizing the composition
WO2010013827A1 (en) 2008-07-29 2010-02-04 住友化学株式会社 Composition comprising phosphorescence emitting compound, and light emitting element using the composition
WO2010013725A1 (en) 2008-07-30 2010-02-04 住友化学株式会社 Laminated structure, method for producing same, and electronic element comprising same
WO2010026972A1 (en) 2008-09-03 2010-03-11 住友化学株式会社 Polymer compound and polymer light-emitting element utilizing same
WO2010041559A1 (en) 2008-10-06 2010-04-15 住友化学株式会社 Polymer compound containing nitrogen-containing heterocyclic structure, and composition, solution, thin film and polymer light-emitting element each containing same
WO2010087510A1 (en) 2009-01-29 2010-08-05 住友化学株式会社 High-molecular compound and light-emitting element using same
WO2010123131A1 (en) 2009-04-23 2010-10-28 住友化学株式会社 Metal complex having aromatic ligand that contains nitrogen atom
WO2011040388A1 (en) 2009-09-30 2011-04-07 住友化学株式会社 Laminated structure, polymer, electroluminescent element, and photoelectric conversion element
WO2011049241A1 (en) 2009-10-22 2011-04-28 住友化学株式会社 Organic electroluminescent element
DE112010004188T5 (en) 2009-10-28 2012-11-22 Sumitomo Chemical Co., Ltd. Metal complex with multidentate ligand
WO2011087058A1 (en) 2010-01-15 2011-07-21 住友化学株式会社 Polymer light emitting element
WO2011093428A1 (en) 2010-01-28 2011-08-04 住友化学株式会社 Polymer compound and light-emitting device using same
WO2011093411A1 (en) 2010-01-29 2011-08-04 住友化学株式会社 Polymer compound, method for producing same, and light-emitting element using the polymer compound
WO2011093460A1 (en) 2010-01-29 2011-08-04 住友化学株式会社 Light-emitting material, ink composition, thin film, light-emitting element, and method for manufacturing a light-emitting element
WO2011105622A1 (en) 2010-02-25 2011-09-01 住友化学株式会社 Fluoranthene polymeric compound
DE112011100845T5 (en) 2010-03-10 2013-01-24 Hiroshima University Thin film and used in the same compound
WO2011132698A1 (en) 2010-04-20 2011-10-27 住友化学株式会社 Organic light-emitting element
US9184388B2 (en) 2010-07-29 2015-11-10 Sumitomo Chemical Company, Limited Layered structure, electronic device using same, aromatic compound, and method for manufacturing said compound
US9837612B2 (en) 2010-12-21 2017-12-05 Sumitomo Chemical Company, Limted Polymer compound and light-emitting device using same
WO2012124770A1 (en) 2011-03-17 2012-09-20 住友化学株式会社 Metal complex compositions and mixture thereof
US9929347B2 (en) 2012-03-27 2018-03-27 Sumitomo Chemical Company, Limtied Polymer compound and light emitting element using same
WO2013146806A1 (en) 2012-03-27 2013-10-03 住友化学株式会社 Polymer compound and light emitting element using same
WO2013151129A1 (en) 2012-04-06 2013-10-10 住友化学株式会社 Organic electroluminescent element and method of manufacturing same
WO2013151170A1 (en) 2012-04-06 2013-10-10 住友化学株式会社 Application system, and method for producing light-emitting device
WO2013151130A1 (en) 2012-04-06 2013-10-10 住友化学株式会社 Organic electroluminescence element and method for manufacturing same
WO2014061493A1 (en) 2012-10-15 2014-04-24 住友化学株式会社 Method for manufacturing electronic device
WO2018146950A1 (en) 2017-02-09 2018-08-16 住友化学株式会社 Method for manufacturing organic electronic device
WO2019078085A1 (en) 2017-10-19 2019-04-25 住友化学株式会社 Organic electronic device manufacturing method
WO2019131145A1 (en) 2017-12-26 2019-07-04 住友化学株式会社 Method for producing electronic device, and electronic device
WO2020039991A1 (en) 2018-08-21 2020-02-27 住友化学株式会社 Method for manufacturing electronic device

Similar Documents

Publication Publication Date Title
JPH02135361A (en) Electrophotographic sensitive body
JPH02135359A (en) Electrophotographic sensitive body
JP2990307B2 (en) Electrophotographic photoreceptor
JPH04338760A (en) Electrophotographic sensitive body
JPH07168377A (en) Electrophotographic photoreceptor
US5011757A (en) Electrophotographic photoreceptor containing a fluorene derivative
JPH07175236A (en) Electrophotographic photoreceptor
JP2518365B2 (en) Electron-accepting compound and method for producing the same
JPH0743918A (en) Electrophotographic photoreceptor
JPH02135357A (en) Electrophotographic sensitive body
JPH02135358A (en) Electrophotographic sensitive body
JPH02135356A (en) Electrophotographic sensitive body
JPH08278647A (en) Electrophotographic photoreceptor
JPH02135362A (en) Electrophotographic sensitive body
JP2518366B2 (en) Electron-accepting compound and method for producing the same
JP3328860B2 (en) Phthalimide compound and electrophotographic photoreceptor containing the same
JPH0452262B2 (en)
JPH02135360A (en) Electrophotographic sensitive body
JPH07160023A (en) Electrophotographic photoreceptor
JP2990305B2 (en) Electrophotographic photoreceptor
JPH07160022A (en) Electrophotographic photoreceptor
JPH07281461A (en) Electrophotographic photoreceptor
JPH05173342A (en) Electrophotographic sensitive body
JPS59214035A (en) Electrophotographic sensitive body
JPS63239455A (en) Electrophotographic sensitive body