JPH0570595A - Hole-transporting high-molecular substance - Google Patents
Hole-transporting high-molecular substanceInfo
- Publication number
- JPH0570595A JPH0570595A JP3231898A JP23189891A JPH0570595A JP H0570595 A JPH0570595 A JP H0570595A JP 3231898 A JP3231898 A JP 3231898A JP 23189891 A JP23189891 A JP 23189891A JP H0570595 A JPH0570595 A JP H0570595A
- Authority
- JP
- Japan
- Prior art keywords
- group
- hole
- methyldichlorosilane
- molecular substance
- polysilane
- 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
Links
- 239000000126 substance Substances 0.000 title claims abstract description 19
- 229920000548 poly(silane) polymer Polymers 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000005103 alkyl silyl group Chemical group 0.000 claims abstract description 4
- 125000005104 aryl silyl group Chemical group 0.000 claims abstract description 4
- 229920001519 homopolymer Polymers 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- QPVNWLRQLVKKPS-UHFFFAOYSA-N dichloro-methyl-(trimethylsilylmethyl)silane Chemical compound C[Si](C)(C)C[Si](C)(Cl)Cl QPVNWLRQLVKKPS-UHFFFAOYSA-N 0.000 abstract description 5
- DWZSONOXRMCFDJ-UHFFFAOYSA-M [Cl-].C[Si](C)(C)[Mg+] Chemical compound [Cl-].C[Si](C)(C)[Mg+] DWZSONOXRMCFDJ-UHFFFAOYSA-M 0.000 abstract description 3
- 239000005055 methyl trichlorosilane Substances 0.000 abstract description 3
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 abstract description 3
- OOCUOKHIVGWCTJ-UHFFFAOYSA-N chloromethyl(trimethyl)silane Chemical compound C[Si](C)(C)CCl OOCUOKHIVGWCTJ-UHFFFAOYSA-N 0.000 abstract description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- -1 porphyrin compounds Chemical class 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 238000010992 reflux Methods 0.000 description 14
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000010408 film Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000010586 diagram Methods 0.000 description 4
- ZLONNNXKSOWPRZ-UHFFFAOYSA-N dichloro-methyl-(2-trimethylsilylethyl)silane Chemical compound C[Si](C)(C)CC[Si](C)(Cl)Cl ZLONNNXKSOWPRZ-UHFFFAOYSA-N 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 3
- 238000005336 cracking Methods 0.000 description 3
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 3
- GCSJLQSCSDMKTP-UHFFFAOYSA-N ethenyl(trimethyl)silane Chemical compound C[Si](C)(C)C=C GCSJLQSCSDMKTP-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000005048 methyldichlorosilane Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 108091008695 photoreceptors Proteins 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012050 conventional carrier Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BESDFAJLHTURGH-UHFFFAOYSA-N dichloro-methyl-(3-trimethylsilylpropyl)silane Chemical compound C[Si](C)(C)CCC[Si](C)(Cl)Cl BESDFAJLHTURGH-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SJHHDDDGXWOYOE-UHFFFAOYSA-N oxytitamium phthalocyanine Chemical compound [Ti+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 SJHHDDDGXWOYOE-UHFFFAOYSA-N 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明はエレクトロルミネッセン
ス素子、フォトレジスト或は電子写真感光体等へ応用さ
れるポリシラン系の正孔輸送性高分子物質に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a polysilane-based hole-transporting polymer substance which is applied to an electroluminescence device, a photoresist, an electrophotographic photoreceptor or the like.
【０００２】[0002]
【従来技術】有機薄膜エレクトロルミネッセンス素子
（ＥＬ素子と略記する）には既に数多くの技術開示があ
り、いづれも略10Ｖ付近で数百cd／m2の高輝度ものが得
られるようになって以来、数多くの研究開発が行われて
いる。更に、ＥＬ素子に用いられる物質についてもポリ
フィリン化合物（特開昭57-51781号）、アルカリ土類金
属（特開昭59-194393号）、金属キレート化合物、芳香
族三級アミン化合物（特開昭63-295695号、特開平2-155
595号）をはじめ、更に特開平1-245087号、同1-256584
号、同1-297490号、同2-88689号、同2-216791号、同2-2
89676号、同2-305886号に提案がある。2. Description of the Related Art There have already been many technical disclosures on organic thin film electroluminescent elements (abbreviated as EL elements), and since it has been possible to obtain a high luminance of several hundred cd / m 2 at about 10 V, any of them has been disclosed. , A lot of research and development is done. Further, regarding substances used for EL devices, porphyrin compounds (JP-A-57-51781), alkaline earth metals (JP-A-59-194393), metal chelate compounds, aromatic tertiary amine compounds (JP-A-Sho). 63-295695, JP-A-2-155
No. 595), and JP-A 1-245087 and 1-256584.
No. 1, No. 1-297490, No. 2-88689, No. 2-216791, No. 2-2
There are suggestions in 89676 and 2-305886.
【０００３】これら従来のＥＬ素子は低電圧で高輝度が
えられるけれども、著しく耐久性が低い、全層蒸着成膜
すると良好な輝度を示すがコスト高であり、低コストの
塗布方式では輝度が上がらない等の欠点がある。Although these conventional EL devices can obtain high brightness at low voltage, they are extremely low in durability, exhibit good brightness when deposited by vapor deposition of all layers, but are expensive, and the brightness is low in a low-cost coating method. There are drawbacks such as not rising.
【０００４】更に特開平3-126787号にはポリシランを使
用したＥＬ素子が提示されているがＡＣ駆動ＥＬはＤＣ
低電圧駆動ができないので周辺回路の簡素化が図れない
等の欠点をもっている。Further, JP-A-3-126787 proposes an EL element using polysilane, but an AC driven EL is a DC element.
Since it cannot be driven at a low voltage, it has a drawback that the peripheral circuits cannot be simplified.
【０００５】更に電子写真感光体の分野においても、感
光体の感光層のキャリア（正孔）輸送物質として特定の
構造のポリシランを用いる技術が提案された（特開昭61
-10747号、同62-269964号、同63-285552号参照）。この
ポリシランによれば、従来のキャリア輸送性物質と異り
自己成膜性を有していて、他のバインダと組合せること
なく容易に膜状の感光層を形成することができ、又、正
孔の移動度が約10-4cm2／V・secオーダもしくはそれ以上
にあって従来のキャリア輸送性物質に比して約１桁以上
大きく、従来のキャリア輸送性物質を用いて構成された
有機感光体の欠点は、この物質を用いることによって解
消される。Further, in the field of electrophotographic photoreceptors, a technique has been proposed in which polysilane having a specific structure is used as a carrier (hole) transporting substance in the photosensitive layer of the photoreceptor (JP-A-61).
-10747, 62-269964, 63-285552). According to this polysilane, unlike the conventional carrier-transporting substance, it has a self-film-forming property, and it is possible to easily form a film-shaped photosensitive layer without combining it with other binders. Pore mobility is on the order of about 10 -4 cm 2 / V · sec or more and is about one digit or more larger than that of conventional carrier transporting materials, and it is composed of conventional carrier transporting materials. The drawbacks of organophotoreceptors are eliminated by using this material.
【０００６】しかし、このポリシランを用いて構成され
た感光層は可撓性に乏しく、又膜強度が概して低く、更
に接着性に乏しい。そのため、可撓性をもったベルト基
体上にポリシランを製膜しても罅割れ、膜剥れ等の損傷
が発生しやすく、更に電子写真プロセスを繰返して遂行
すると、更にこの現象が進行し拡大してゆく。However, the photosensitive layer formed by using this polysilane has poor flexibility, and generally has low film strength and poor adhesiveness. Therefore, even if a polysilane film is formed on a flexible belt substrate, damage such as cracking and film peeling is likely to occur, and when the electrophotographic process is repeated, this phenomenon further progresses and spreads. Do it.
【０００７】[0007]
【発明の目的】本発明の目的は前記の状況に基き、
（１）正孔輸送能に優れ、かつ高輝度を与え、（２）可
撓性、機械的強度、接着性に優れ更に高耐久性であり、
（３）塗布による成膜が可能で、罅割れ、膜剥れを起さ
ぬ、正孔輸送性の高分子物質を提供することにある。The object of the present invention is based on the above situation.
(1) It has an excellent hole-transporting ability and gives high brightness, and (2) it has excellent flexibility, mechanical strength, and adhesiveness, and has high durability.
(3) It is intended to provide a high molecular substance having a hole transporting property, which can be formed into a film by coating and does not cause cracking or film peeling.
【０００８】[0008]
【発明の構成】前記本発明の目的は、下記一般式（１）
で表される繰返し単位を有する単独重合体もしくは前記
単位を含有するポリシラン系正孔輸送性高分子物質によ
って達成される。The above-mentioned object of the present invention is represented by the following general formula (1):
This is achieved by a homopolymer having a repeating unit represented by or a polysilane-based hole transporting polymer substance containing the above unit.
【０００９】[0009]
【化２】 [Chemical 2]
【００１０】式中Ｒ1，Ｒ2，Ｒ3及びＲ4は夫々水素原
子、置換もしくは無置換のアルキル基、アルコキシ基、
アルケニル基、アリール基、アルキルシリル基又はアリ
ールシリル基である。ｎは自然数である。ｎには特に制
約はないが１〜５が好ましい。In the formula, R 1 , R 2 , R 3 and R 4 are each a hydrogen atom, a substituted or unsubstituted alkyl group, an alkoxy group,
It is an alkenyl group, an aryl group, an alkylsilyl group or an arylsilyl group. n is a natural number. There is no particular restriction on n, but 1 to 5 is preferable.
【００１１】また前記一般式（１）のＲ1〜Ｒ4の表すア
ルキル基としては、炭素数が１〜24、好ましくは１〜８
の直鎖又は枝分かれしたアルキル基、例えばメチル基、
エチル基、プロピル基、ブチル基、アミル基、ヘキシル
基、オクチル基、ノニル基、デシル基、ペンタデシル
基、ステアリル基、シクロヘキシル基などのシクロアル
キル基、これらの置換アルキル基等を挙げることができ
る。The alkyl group represented by R 1 to R 4 in the general formula (1) has 1 to 24 carbon atoms, preferably 1 to 8 carbon atoms.
A linear or branched alkyl group of, for example, a methyl group,
Examples thereof include ethyl groups, propyl groups, butyl groups, amyl groups, hexyl groups, octyl groups, nonyl groups, decyl groups, pentadecyl groups, stearyl groups, cycloalkyl groups such as cyclohexyl groups, and substituted alkyl groups thereof.
【００１２】アリール基としては、炭素数が６〜24のも
のが好ましく、フェニル基、ナフチル基、アンスリル基
等を挙げることができる。The aryl group preferably has 6 to 24 carbon atoms, and examples thereof include a phenyl group, a naphthyl group and an anthryl group.
【００１３】アルコキシ基としては、炭素数が１〜約10
のものが好ましく、例えばメトキシ基、エトキシ基、プ
ロポキシ基、ブトキシ基を挙げることができる。The alkoxy group has 1 to about 10 carbon atoms.
And a methoxy group, an ethoxy group, a propoxy group and a butoxy group can be exemplified.
【００１４】アルケニル基としては、炭素数が２〜約10
のものが好ましく、ビニル基、アリル基、ブテニル基等
が挙げられる。The alkenyl group has 2 to about 10 carbon atoms.
The vinyl group, the allyl group, the butenyl group and the like are preferable.
【００１５】アルキルシリル基としては、-SiH(CH3)2，
-Si(CH3)3，-Si(C2H5)3，-Si(C3H7)3，-Si(C4H9)3，-Si
(CH3)2(C2H5)，-Si(CH3)(C2H5)2などを挙げることがで
きる。As the alkylsilyl group, --SiH (CH 3 ) 2 ,
-Si (CH 3) 3, -Si (C 2 H 5) 3, -Si (C 3 H 7) 3, -Si (C 4 H 9) 3, -Si
(CH 3) 2 (C 2 H 5), - Si (CH 3) (C 2 H 5) 2 , and the like.
【００１６】アリールシリル基としては-SiH(C6H5)2、-
Si(CH3)2(C6H5)、-CH2Si(CH3)2(C6H5）などを挙げるこ
とができる。As the arylsilyl group, -SiH (C 6 H 5 ) 2 ,-
Si (CH 3) 2 (C 6 H 5), - CH 2 Si (CH 3) 2 (C 6 H 5) , and the like.
【００１７】前記Ｒ1〜Ｒ4及びアリール基への置換基と
しては、アルキル基、アルコキシ基、アリール基、アミ
ノ基、ニトロ基、シアノ基及びハロゲン原子或はその他
の置換基が挙げられる。Examples of the substituents on R 1 to R 4 and the aryl group include an alkyl group, an alkoxy group, an aryl group, an amino group, a nitro group, a cyano group, a halogen atom and other substituents.
【００１８】一般式（１）モノマー単位と共重合させる
シランモノマー単位としては好ましいものとして下記の
ものが挙げられる。尚水素又は置換基を有する２価のモ
ノシラン残基等の構造を-(R1)Si(R2)-，-(R1)2Si-のよ
うに表示する。Preferred examples of the silane monomer unit copolymerized with the monomer unit of the general formula (1) include the following. The structure of hydrogen or a divalent monosilane residue having a substituent is represented as-(R 1 ) Si (R 2 )-and-(R 1 ) 2 Si-.
【００１９】[0019]
【化３】 [Chemical 3]
【００２０】[0020]
【化４】 [Chemical 4]
【００２１】次に本発明に係るポリシラン系高分子物質
の合成例を示す。Next, a synthesis example of the polysilane polymer material according to the present invention will be shown.
【００２２】（モノマーの合成）本発明に係るモノマー
は下記反応式によって得ることができる。(Synthesis of Monomer) The monomer according to the present invention can be obtained by the following reaction formula.
【００２３】[0023]
【化５】 [Chemical 5]
【００２４】（１）（トリメチルシリルメチル）メチル
ジクロルシラン 滴下漏斗、還流冷却器、撹拌機および窒素導入管をつけ
た300mlフラスコに、マグネシウム5.8g（0.24mmol）と
ジエチルエーテル100mlを入れた。撹拌しながら、これ
にクロルメチルトリメチルシラン24.4g（0.20mol）のジ
エチルエーテル（50ml）溶液を２時間かけて滴下した。
滴下終了後、12時間撹拌し塩化トリメチルシリルマグネ
シウムを調製した。(1) (Trimethylsilylmethyl) methyldichlorosilane In a 300 ml flask equipped with a dropping funnel, a reflux condenser, a stirrer and a nitrogen inlet tube, 5.8 g (0.24 mmol) of magnesium and 100 ml of diethyl ether were placed. With stirring, a solution of chloromethyltrimethylsilane (24.4 g, 0.20 mol) in diethyl ether (50 ml) was added dropwise thereto over 2 hours.
After completion of dropping, the mixture was stirred for 12 hours to prepare trimethylsilylmagnesium chloride.
【００２５】滴下漏斗、還流冷却器、撹拌機および窒素
導入管をつけた１ｌフラスコに、メチルトリクロルシラ
ン149g（１mol）とジエチルエーテル250mlを入れた。撹
拌しながら、この混合物に前記調製した塩化トリメチル
シリルマグネシウムを２時間かけて滴下した。滴下終了
後、36時間撹拌しながら加熱還流した。冷却後、反応混
合物にヘキサン200mlを加え、生成した塩を濾別した。
濾液を濃縮後、減圧蒸留し、（トリメチルシリルメチ
ル）メチルジクロルシランを得た。収量11.7g（収率43
％）。A 1-liter flask equipped with a dropping funnel, a reflux condenser, a stirrer and a nitrogen inlet tube was charged with 149 g (1 mol) of methyltrichlorosilane and 250 ml of diethyl ether. While stirring, the trimethylsilylmagnesium chloride prepared above was added dropwise to this mixture over 2 hours. After completion of the dropping, the mixture was heated under reflux for 36 hours with stirring. After cooling, 200 ml of hexane was added to the reaction mixture, and the produced salt was filtered off.
The filtrate was concentrated and then distilled under reduced pressure to obtain (trimethylsilylmethyl) methyldichlorosilane. Yield 11.7g (Yield 43
%).
【００２６】［参考文献］D.Seyferth and E.G.Rochow,
J.Org.Chem., 20, 250 (1955)。[Reference] D. Seyferth and EGRochow,
J. Org. Chem., 20 , 250 (1955).
【００２７】（２）（2-トリメチルシリルエチル）メチ
ルジクロルシラン トリメチルシリルエテン100g（1.0mmol）とメチルジク
ロルシラン127g（1.1mol）を反応させた。滴下漏斗、還
流冷却器、撹拌機および窒素導入管をつけた500mlフラ
スコに、トリメチルシリルエテンとメチルジクロルシラ
ンの混合物20mlを入れ、塩化白金酸（ＶＩ）0.0051g
（0.01mmol）を加えた。撹拌しながら、これに残りのト
リメチルシリルエテンとメチルジクロルシランの混合物
を４時間かけて滴下した。滴下終了後、１時間撹拌し反
応を完結させた。反応混合物にヘキサン200mlを加え、
沈殿した触媒を濾別した。濾液を濃縮後、減圧蒸留し、
（2-トリメチルシリルエチル）メチルジクロルシランを
得た。収量145g（収率75％）。 ［参考文献］J.W.Ryan, G.K.Menzie, and J.L.Speier,
J.Am.Chem.Soc.,82,3601(1960)。(2) (2-Trimethylsilylethyl) methyldichlorosilane 100 g (1.0 mmol) of trimethylsilylethene was reacted with 127 g (1.1 mol) of methyldichlorosilane. 20 ml of a mixture of trimethylsilylethene and methyldichlorosilane was placed in a 500 ml flask equipped with a dropping funnel, a reflux condenser, a stirrer and a nitrogen introducing tube, and 0.0051 g of chloroplatinic acid (VI) was added.
(0.01 mmol) was added. With stirring, the remaining mixture of trimethylsilylethene and methyldichlorosilane was added dropwise thereto over 4 hours. After completion of dropping, the reaction was completed by stirring for 1 hour. 200 ml of hexane was added to the reaction mixture,
The precipitated catalyst was filtered off. After the filtrate is concentrated, it is distilled under reduced pressure,
(2-Trimethylsilylethyl) methyldichlorosilane was obtained. Yield 145 g (75% yield). [References] JWRyan, GKMenzie, and JLSpeier,
J. Am. Chem. Soc., 82 , 3601 (1960).
【００２８】[0028]
【実施例】次に実施例によって前記モノマーを用いて合
成する本発明のポリシランについて具体的に説明する。EXAMPLES Next, the polysilane of the present invention synthesized by using the above-mentioned monomers will be specifically described by way of Examples.
【００２９】（１）ポリ［（トリメチルシリルメチル）
メチルシリレン］の合成 実施例１ 滴下漏斗、還流冷却器、撹拌機及び窒素導入管をつけた
500mlフラスコに、（トリメチルシリルエチル）メチル
ジクロルシラン20g(100mmol)とトルエン200mlを入れ
た。これに加熱（110℃）し撹拌しながら、ナトリウム
（5.3g、270mmol）のトルエン（100ml）スラリーを30分
かけて滴下した。滴下終了後、72時間撹拌しながら加熱
還流した。冷却後、反応混合物にヘキサン50mlとメタノ
ール50mlを加え、未反応のナトリウムを分解した。希塩
酸100mlを加えた後、溶媒相を分離し、水相をヘキサン
で抽出した。分離液と抽出液を合せ、水洗し無水硫酸マ
グネシウムで乾かし、ロータリエバポレータで溶媒を溜
去した。残渣をアセトンで洗い、真空乾燥し、ポリマー
を得た。収量0.50g（収率４％）。Mw＝9.8×105，Mw/Mn
＝1.6。(1) Poly [(trimethylsilylmethyl)
Synthesis of methylsilylene] Example 1 A dropping funnel, a reflux condenser, a stirrer and a nitrogen inlet tube were attached.
A 500 ml flask was charged with 20 g (100 mmol) of (trimethylsilylethyl) methyldichlorosilane and 200 ml of toluene. To this, a toluene (100 ml) slurry of sodium (5.3 g, 270 mmol) was added dropwise over 30 minutes while heating (110 ° C.) and stirring. After completion of the dropping, the mixture was heated under reflux for 72 hours with stirring. After cooling, 50 ml of hexane and 50 ml of methanol were added to the reaction mixture to decompose unreacted sodium. After adding 100 ml of dilute hydrochloric acid, the solvent phase was separated and the aqueous phase was extracted with hexane. The separated liquid and the extracted liquid were combined, washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off with a rotary evaporator. The residue was washed with acetone and vacuum dried to obtain a polymer. Yield 0.50 g (4% yield). Mw = 9.8 × 10 5 , Mw / Mn
= 1.6.
【００３０】実施例２ 滴下漏斗、還流冷却器、撹拌機及び窒素導入管をつけた
300mlフラスコに、ナトリウムとトルエンを入れ、加熱
し激しく撹拌し、ナトリウムを細粒状にした。これに、
加熱（110℃）し撹拌しながら（トリメチルシリルメチ
ル）メチルジクロルシラン7.5g（37mmol）のトルエン80
ml溶液を１時間かけ滴下した。滴下終了後、66時間撹拌
しながら加熱還流した。冷却後、反応混合物にヘキサン
50mlとメタノール50mlを加え、未反応のナトリウムを分
解した。希塩酸100mlを加えた後、溶媒相を分解し、水
相をヘキサンで抽出した。分離液と抽出液を合せ、水洗
し無水硫酸マグネシウムで乾かし、ロータリエバポレー
タで溶媒を溜去した。残渣をアセトンで洗い、真空乾燥
し、ポリマーを得た。収量0.30g（収率６％）。Mw＝9.8
×105，Mw/Mn＝1.6。Example 2 A dropping funnel, a reflux condenser, a stirrer and a nitrogen inlet tube were attached.
Sodium and toluene were placed in a 300 ml flask, and the mixture was heated and vigorously stirred to finely granulate the sodium. to this,
While heating (110 ° C) and stirring, (trimethylsilylmethyl) methyldichlorosilane 7.5 g (37 mmol) toluene 80
The ml solution was added dropwise over 1 hour. After completion of the dropping, the mixture was heated under reflux for 66 hours while stirring. After cooling, add hexane to the reaction mixture.
50 ml and 50 ml of methanol were added to decompose unreacted sodium. After adding 100 ml of dilute hydrochloric acid, the solvent phase was decomposed and the aqueous phase was extracted with hexane. The separated liquid and the extracted liquid were combined, washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off with a rotary evaporator. The residue was washed with acetone and vacuum dried to obtain a polymer. Yield 0.30 g (yield 6%). Mw = 9.8
× 10 5 , Mw / Mn = 1.6.
【００３１】実施例３ 滴下漏斗、還流冷却器、撹拌機及び窒素導入管をつけた
200mlフラスコに、（トリメチルシリルメチル）メチル
ジクロルシラン10g（50mmol）、18-クラウン-6；0.66g
（2.5mmol）及びジエチルエーテル50mlを入れた。これ
に加熱（35℃）し撹拌しながら、ナトリウム（2.7g、11
7mmol）のジエチルエーテル（100ml）スラリーを30分か
けて滴下した。滴下終了後、46時間撹拌しながら加熱還
流した。冷却後、反応混合物にヘキサン50mlとメタノー
ル50mlを加え、未反応のナトリウムを分解した。希塩酸
100mlを加えた後、溶媒相を分解し、水相をヘキサンで
抽出した。分離液と抽出液を合せ、水洗し無水硫酸マグ
ネシウムで乾かし、ロータリエバポレータで溶媒を溜去
した。残渣をアセトンで洗い、真空乾燥し、ポリマーを
得た。収量3.7g（収率57％）。Mw＝9.2×104，Mw/Mn＝
2.3。Example 3 A dropping funnel, a reflux condenser, a stirrer and a nitrogen inlet tube were attached.
In a 200 ml flask, (trimethylsilylmethyl) methyldichlorosilane 10 g (50 mmol), 18-crown-6; 0.66 g
(2.5 mmol) and 50 ml of diethyl ether were added. While heating (35 ° C) and stirring, add sodium (2.7 g, 11
A 7 mmol) slurry of diethyl ether (100 ml) was added dropwise over 30 minutes. After completion of the dropping, the mixture was heated to reflux with stirring for 46 hours. After cooling, 50 ml of hexane and 50 ml of methanol were added to the reaction mixture to decompose unreacted sodium. Dilute hydrochloric acid
After adding 100 ml, the solvent phase was decomposed and the aqueous phase was extracted with hexane. The separated liquid and the extracted liquid were combined, washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off with a rotary evaporator. The residue was washed with acetone and vacuum dried to obtain a polymer. Yield 3.7 g (57% yield). Mw = 9.2 × 10 4 , Mw / Mn =
2.3.
【００３２】得られたポリ［（トリメチルシリルメチ
ル）メチルシリレン］のＩＲスペクトルデータを図１
に、NMRスペクトルを図２に示す。The IR spectrum data of the obtained poly [(trimethylsilylmethyl) methylsilylene] is shown in FIG.
The NMR spectrum is shown in FIG.
【００３３】（２）ポリ［（2-トリメチルシリルエチ
ル）メチルシリレン］の合成 実施例４ 滴下漏斗、還流冷却器、撹拌機及び窒素導入管をつけた
200mlフラスコに、（2-トリメチルシリルエチル）メチ
ルジクロルシラン10g（50mmol）、15-クラウン-5；0.20
g（１mmol）及びトルエン100mlを入れた。これに加熱
（110℃）し撹拌しながら、ナトリウム（2.3g、100mmo
l）のトルエン（40ml）スラリーを30分かけて滴下し
た。滴下終了後、46時間撹拌しながら加熱還流した。冷
却後、反応混合物にヘキサン50mlとメタノール50mlを加
え、未反応のナトリウムを分解した。希塩酸100mlを加
えた後、溶媒相を分解し、水相をヘキサンで抽出した。
分離液と抽出液を合せ、水洗し無水硫酸マグネシウムで
乾かし、ロータリエバポレータで溶媒を溜去した。残渣
をアセトンで洗い、真空乾燥し、ポリマーを得た。収量
2.0g（収率30％）。Mw＝1.6×105，Mw/Mn＝2.5。(2) Synthesis of poly [(2-trimethylsilylethyl) methylsilylene] Example 4 A dropping funnel, a reflux condenser, a stirrer and a nitrogen inlet tube were attached.
In a 200 ml flask, (2-trimethylsilylethyl) methyldichlorosilane 10 g (50 mmol), 15-crown-5; 0.20
g (1 mmol) and 100 ml of toluene were added. While heating (110 ℃) and stirring, add sodium (2.3g, 100mmo
l) Toluene (40 ml) slurry was added dropwise over 30 minutes. After completion of the dropping, the mixture was heated to reflux with stirring for 46 hours. After cooling, 50 ml of hexane and 50 ml of methanol were added to the reaction mixture to decompose unreacted sodium. After adding 100 ml of dilute hydrochloric acid, the solvent phase was decomposed and the aqueous phase was extracted with hexane.
The separated liquid and the extracted liquid were combined, washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off with a rotary evaporator. The residue was washed with acetone and vacuum dried to obtain a polymer. yield
2.0 g (yield 30%). Mw = 1.6 × 10 5 , Mw / Mn = 2.5.
【００３４】得られたポリ［（2-トリメチルシリルエチ
ル）メチルシリレン］のＩＲスペクトルデータを図３
に、NMRスペクトルを図４に示す。The IR spectrum data of the obtained poly [(2-trimethylsilylethyl) methylsilylene] is shown in FIG.
The NMR spectrum is shown in FIG.
【００３５】（３）ポリ［（3-トリメチルシリルプロピ
ル）メチルシリレン］の合成 実施例５ 滴下漏斗、還流冷却器、撹拌機及び窒素導入管をつけた
300mlフラスコに、（3-トリメチルシリルプロピル）メ
チルジクロルシラン10g（43mmol）、15-クラウン-5；0.
48g（2.2mmol）及びジエチルエーテル80mlを入れた。こ
れに加熱（35℃）し撹拌しながら、ナトリウム（2.4g、
104mmol）のジエチメエーテル（120ml）スラリーを30分
かけて滴下した。滴下終了後、46時間撹拌しながら加熱
還流した。冷却後、反応混合物にヘキサン50mlとメタノ
ール50mlを加え、未反応のナトリウムを分解した。希塩
酸100mlを加えた後、溶媒相を分解し、水相をヘキサン
で抽出した。分離液と抽出液を合せ、水洗し無水硫酸マ
グネシウムで乾かし、ロータリエバポレータで溶媒を溜
去した。残渣をアセトンで洗い、真空乾燥し、ポリマー
を得た。収量1.0g（収率15％）。Mw＝3.6×104，Mw/Mn
＝1.7。(3) Synthesis of poly [(3-trimethylsilylpropyl) methylsilylene] Example 5 A dropping funnel, a reflux condenser, a stirrer and a nitrogen inlet tube were attached.
In a 300 ml flask, (3-trimethylsilylpropyl) methyldichlorosilane 10 g (43 mmol), 15-crown-5;
48 g (2.2 mmol) and 80 ml of diethyl ether were added. While heating (35 ° C) and stirring, sodium (2.4 g,
A 104 mmol) diethyl ether (120 ml) slurry was added dropwise over 30 minutes. After completion of the dropping, the mixture was heated to reflux with stirring for 46 hours. After cooling, 50 ml of hexane and 50 ml of methanol were added to the reaction mixture to decompose unreacted sodium. After adding 100 ml of dilute hydrochloric acid, the solvent phase was decomposed and the aqueous phase was extracted with hexane. The separated liquid and the extracted liquid were combined, washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off with a rotary evaporator. The residue was washed with acetone and vacuum dried to obtain a polymer. Yield 1.0 g (15% yield). Mw = 3.6 × 10 4 , Mw / Mn
= 1.7.
【００３６】得られたポリ［（3-トリメチルシリルプロ
ピル）メチルシリレン］のＩＲスペクトルデータを図５
に、NMRスペクトルを図６に示す。The IR spectrum data of the obtained poly [(3-trimethylsilylpropyl) methylsilylene] is shown in FIG.
The NMR spectrum is shown in FIG.
【００３７】前記実施例によってえられるポリシランを
下記に示す。The polysilanes obtained in the above examples are shown below.
【００３８】[0038]
【化６】 [Chemical 6]
【００３９】[0039]
【化７】 [Chemical 7]
【００４０】[0040]
【化８】 [Chemical 8]
【００４１】正孔移動度測定 スライドガラス上にAl電極を蒸着した。Ｙ型チタニルフ
タロシアニン １重量部、ポリビニルブチラール樹脂
１重量部、酢酸t-ブチル 100重量部をサンドグライン
ダで分散し、この分散液を前述のAl電極上に電荷発生層
を0.3μm形成した。更にＰ−１をトルエンに18wt％で溶
解し、その溶液にて電荷輸送層を15μm形成した。更に
この上に半透明の金電極を形成し、TOF（Time of Fligh
t）測定サンプルとした。Measurement of hole mobility An Al electrode was vapor-deposited on a slide glass. Y-type titanyl phthalocyanine 1 part by weight, polyvinyl butyral resin
1 part by weight and 100 parts by weight of t-butyl acetate were dispersed by a sand grinder, and this dispersion was used to form a charge generation layer of 0.3 μm on the Al electrode. Further, P-1 was dissolved in toluene at 18 wt%, and the solution formed a charge transport layer of 15 μm. Furthermore, a semi-transparent gold electrode is formed on top of this, and TOF (Time of Fligh
t) Used as a measurement sample.
【００４２】TOF測定はJournal of polymer Science Pa
rtＡ vol.25,823〜827（1987），Ｍ． Stolka et alに
記載方法と実質的に同一方法で行った。TOF is measured in the Journal of polymer Science Pa
rtA vol.25, 823-827 (1987), M.A. Substantially the same as described in Stolka et al.
【００４３】その結果23℃下で印加電圧600Ｖで1.4×10
-5cm2／V・sの移動度μを示した。As a result, 1.4 × 10 at an applied voltage of 600 V at 23 ° C.
The mobility μ of −5 cm 2 / V · s was shown.
【００４４】Ｐ-２，３及びポリメチルフェニルシラン
についても同様に行った。The same procedure was performed for P-2,3 and polymethylphenylsilane.
【００４５】 可撓性測定 75μmポリエチレンテレフタレート（ＰＥＴ）ベース上
にＰ−１トルエン溶液（18wt％）からＰ−１を15μm塗
工した。[0045] Flexibility measurement P-1 was coated on a 75 μm polyethylene terephthalate (PET) base from a P-1 toluene solution (18 wt%) in a thickness of 15 μm.
【００４６】このＰ−１が塗工されたＰＥＴベースを折
曲げて、その可撓性を調べた。The PET base coated with P-1 was bent to examine its flexibility.
【００４７】Ｐ−２，３及び比較のポリメチルフェニル
シランについても同様に試料を作成と、同様のテストを
行った。With respect to P-2,3 and comparative polymethylphenylsilane, samples were prepared in the same manner and the same test was conducted.
【００４８】 Ｐ−１ 罅割れ、膜剥れ無、可撓性良好。P-1 No cracking, no film peeling, good flexibility.
【００４９】 Ｐ−２ 〃 〃 〃 Ｐ−３ 〃 〃 〃 ポリメチルフェニルシラン 罅割れ、膜剥れ著しい。可撓性劣。P-2 〃 〃 〃 P-3 〃 〃 〃 Polymethylphenylsilane Cracks and film peeling are remarkable. Poor flexibility.
【００５０】[0050]
【発明の効果】塗布方式の採用が可能となり、しかも輝
度、耐久性が高く、物性的に強靭で接着性良好な正孔輸
送性高分子物質が提供できる。EFFECT OF THE INVENTION It is possible to provide a hole transporting polymer substance which can be applied by a coating method, has high brightness and durability, is tough in terms of physical properties, and has good adhesiveness.
【図１】ポリ〔(トリメチルシリルメチル)メチルシリレ
ン〕のＩＲスペクトル図FIG. 1 is an IR spectrum diagram of poly [(trimethylsilylmethyl) methylsilylene].
【図２】ポリ〔(トリメチルシリルメチル)メチルシリレ
ン〕の1HNMRスペクトル図FIG. 2 1 H NMR spectrum of poly [(trimethylsilylmethyl) methylsilylene]
【図３】ポリ〔(2-トリメチルシリルエチル)メチルシリ
レン〕のＩＲスペクトル図FIG. 3 is an IR spectrum diagram of poly [(2-trimethylsilylethyl) methylsilylene].
【図４】ポリ〔(2-トリメチルシリルエチル)メチルシリ
レン〕の1HNMRスペクトル図FIG. 4 1 H NMR spectrum diagram of poly [(2-trimethylsilylethyl) methylsilylene]
【図５】ポリ〔(3-トリメチルシリルプロピル)メチルシ
リレン〕のＩＲスペクトル図FIG. 5: IR spectrum of poly [(3-trimethylsilylpropyl) methylsilylene]
【図６】ポリ〔(3-トリメチルシリルプロピル)メチルシ
リレン〕の1HNMRスペクトル図FIG. 6 1 H NMR spectrum diagram of poly [(3-trimethylsilylpropyl) methylsilylene]
Claims (1)
を有する単独重合体もしくは前記単位を含有するポリシ
ラン系正孔輸送性高分子物質。 【化１】 〔式中Ｒ1,Ｒ2,Ｒ3及びＲ4は夫々水素原子、置換もしく
は無置換の続記６つの基；アルキル基、アルコキシ基、
アルケニル基、アリール基、アルキルシリル基又はアリ
ールシリル基である。ｎは自然数である。〕1. A homopolymer having a repeating unit represented by the following general formula (1) or a polysilane-based hole-transporting polymeric substance containing the unit. [Chemical 1] [Wherein R 1 , R 2 , R 3 and R 4 are each a hydrogen atom, a substituted or unsubstituted 6 group; an alkyl group, an alkoxy group,
It is an alkenyl group, an aryl group, an alkylsilyl group or an arylsilyl group. n is a natural number. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3231898A JPH0570595A (en) | 1991-09-11 | 1991-09-11 | Hole-transporting high-molecular substance |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3231898A JPH0570595A (en) | 1991-09-11 | 1991-09-11 | Hole-transporting high-molecular substance |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0570595A true JPH0570595A (en) | 1993-03-23 |
Family
ID=16930772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3231898A Pending JPH0570595A (en) | 1991-09-11 | 1991-09-11 | Hole-transporting high-molecular substance |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0570595A (en) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0711244A (en) * | 1993-06-24 | 1995-01-13 | Mitsui Petrochem Ind Ltd | Thin film element emitting light in electric field and method for producing same |
| US5908687A (en) * | 1996-12-16 | 1999-06-01 | Tohoku Ricoh Co., Ltd. | Heat-sensitive stencil and method of fabricating same |
| US6285059B1 (en) * | 1999-03-18 | 2001-09-04 | United Microelectronics Corp. | Structure for laterally diffused metal-oxide semiconductor |
| US6389964B1 (en) | 1999-04-28 | 2002-05-21 | Tohoku Ricoh Co., Ltd. | Stencil printer |
| EP1600822A2 (en) | 2004-05-25 | 2005-11-30 | Ricoh Company, Ltd. | Electrophotographic photoreceptor and image forming method, apparatus and process cartridge therefor using the photoreceptor |
| KR100706091B1 (en) * | 2004-06-25 | 2007-04-11 | 세이코 엡슨 가부시키가이샤 | Organic electroluminescent device, method for producing the same, and electronic apparatus |
| US7416823B2 (en) | 2004-01-15 | 2008-08-26 | Ricoh Company, Ltd. | Electrophotographic photoconductor, and image formation method, image formation apparatus, and process cartridge for image formation apparatus using the same |
| EP2017676A1 (en) | 2006-04-17 | 2009-01-21 | Ricoh Company, Ltd. | Image forming apparatus, image forming method, and process cartridge |
| US7865114B2 (en) | 2006-11-21 | 2011-01-04 | Ricoh Company Limited | Image forming apparatus, image forming method and process cartridge |
| US7914959B2 (en) | 2005-11-28 | 2011-03-29 | Ricoh Company, Limited | Image bearing member, image forming method, and image forming apparatus |
| US8043773B2 (en) | 2006-11-16 | 2011-10-25 | Ricoh Company, Limited | Image bearing member, image forming apparatus and process cartridge |
| US8148038B2 (en) | 2007-07-02 | 2012-04-03 | Ricoh Company, Ltd. | Image bearing member, process cartridge, image forming apparatus and method of forming image bearing member |
| WO2012099182A1 (en) | 2011-01-21 | 2012-07-26 | Ricoh Company, Ltd. | Electrophotographic photoconductor, and image forming method, image forming apparatus, and process cartridge using the electrophotographic photoconductor |
| EP2824130A4 (en) * | 2012-03-07 | 2015-10-14 | Nippon Soda Co | Method for producing polydialkylsilane |
| US9535344B2 (en) | 2014-12-26 | 2017-01-03 | Ricoh Company, Ltd. | Photoconductor, image-forming apparatus, and cartridge |
-
1991
- 1991-09-11 JP JP3231898A patent/JPH0570595A/en active Pending
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0711244A (en) * | 1993-06-24 | 1995-01-13 | Mitsui Petrochem Ind Ltd | Thin film element emitting light in electric field and method for producing same |
| US5908687A (en) * | 1996-12-16 | 1999-06-01 | Tohoku Ricoh Co., Ltd. | Heat-sensitive stencil and method of fabricating same |
| US6285059B1 (en) * | 1999-03-18 | 2001-09-04 | United Microelectronics Corp. | Structure for laterally diffused metal-oxide semiconductor |
| US6389964B1 (en) | 1999-04-28 | 2002-05-21 | Tohoku Ricoh Co., Ltd. | Stencil printer |
| US7416823B2 (en) | 2004-01-15 | 2008-08-26 | Ricoh Company, Ltd. | Electrophotographic photoconductor, and image formation method, image formation apparatus, and process cartridge for image formation apparatus using the same |
| EP1600822A2 (en) | 2004-05-25 | 2005-11-30 | Ricoh Company, Ltd. | Electrophotographic photoreceptor and image forming method, apparatus and process cartridge therefor using the photoreceptor |
| KR100706091B1 (en) * | 2004-06-25 | 2007-04-11 | 세이코 엡슨 가부시키가이샤 | Organic electroluminescent device, method for producing the same, and electronic apparatus |
| US7914959B2 (en) | 2005-11-28 | 2011-03-29 | Ricoh Company, Limited | Image bearing member, image forming method, and image forming apparatus |
| EP2017676A1 (en) | 2006-04-17 | 2009-01-21 | Ricoh Company, Ltd. | Image forming apparatus, image forming method, and process cartridge |
| US8043773B2 (en) | 2006-11-16 | 2011-10-25 | Ricoh Company, Limited | Image bearing member, image forming apparatus and process cartridge |
| US7865114B2 (en) | 2006-11-21 | 2011-01-04 | Ricoh Company Limited | Image forming apparatus, image forming method and process cartridge |
| US8148038B2 (en) | 2007-07-02 | 2012-04-03 | Ricoh Company, Ltd. | Image bearing member, process cartridge, image forming apparatus and method of forming image bearing member |
| WO2012099182A1 (en) | 2011-01-21 | 2012-07-26 | Ricoh Company, Ltd. | Electrophotographic photoconductor, and image forming method, image forming apparatus, and process cartridge using the electrophotographic photoconductor |
| EP2824130A4 (en) * | 2012-03-07 | 2015-10-14 | Nippon Soda Co | Method for producing polydialkylsilane |
| US9535344B2 (en) | 2014-12-26 | 2017-01-03 | Ricoh Company, Ltd. | Photoconductor, image-forming apparatus, and cartridge |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0570595A (en) | Hole-transporting high-molecular substance | |
| CA1300796C (en) | Ladder polysilanes | |
| WO2004018488A1 (en) | π-CONJUGATED ORGANIC MATERIAL OF POLYCYCLIC FUSED RING TYPE, INTERMEDIATE THEREFOR, AND PROCESS FOR PRODUCING π-CONJUGATED ORGANIC MATERIAL OF POLYCYCLIC FUSED RING TYPE | |
| US5420238A (en) | Poly(silyleneethynylene phenyleneethynylenes), method for preparing same and hardened product thereof | |
| JP3459985B2 (en) | Method for producing thin film of borazine-containing silicon polymer and borazine-containing silicon polymer | |
| US7973190B2 (en) | Polycyclic fused ring type π-conjugated organic material, intermediate therefor, process for producing polycyclic fused ring type π-conjugated organic material, and process for producing intermediate of polycyclic fused ring type π-conjugated organic material | |
| JPH05310942A (en) | Silsequioxane ladder polymer and its production | |
| JPH0995537A (en) | Polysilane compound, its production and raw material therefor | |
| JPH0570772A (en) | Thin-film organic electroluminescence element | |
| JPH0827275A (en) | N-carbazolylpolysilane and organo-n-carbazolyldihalogenosilane compound | |
| JP3089416B1 (en) | Polycarbosilane and method for producing the same | |
| JPH07309882A (en) | New organohalosilane compound | |
| JP2914221B2 (en) | New organohalosilane compounds | |
| JP3567250B2 (en) | Aromatic polycarbosilanes | |
| JP3076845B1 (en) | Organosilicon polymer having functional group and method for producing the same | |
| JP2634430B2 (en) | Ladder-like polysilanes and method for producing the same | |
| JP3673855B2 (en) | Polycarbosilanes having functional groups and method for producing the same | |
| JP5650959B2 (en) | Luminescent material having phthalocyanine in side chain and method for producing the same | |
| JP3425318B2 (en) | Organosilicon polymer and method for producing the same | |
| JP2003531942A (en) | Curable silicone resin composition and reactive silicon compound | |
| JP2576312B2 (en) | Polysilane film composition and crosslinked polysilane film | |
| JP2001261836A (en) | Method for producing aromatic polycarbosilane | |
| JP2671951B2 (en) | Tristanylene-containing polymer and method for producing the same | |
| JP2721860B2 (en) | Method for producing polysilane compound | |
| JP3398425B2 (en) | Polybenzobisoxazole having organopolysiloxane side chain and method for producing the same |