JPH0547533B2 - - Google Patents
Info
- Publication number
- JPH0547533B2 JPH0547533B2 JP58064528A JP6452883A JPH0547533B2 JP H0547533 B2 JPH0547533 B2 JP H0547533B2 JP 58064528 A JP58064528 A JP 58064528A JP 6452883 A JP6452883 A JP 6452883A JP H0547533 B2 JPH0547533 B2 JP H0547533B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- unsubstituted
- chlorine
- lower alkyl
- alkyl group
- 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.)
- Expired - Lifetime
Links
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 108091008695 photoreceptors Proteins 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- -1 halogen ion Chemical class 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 229910052711 selenium Inorganic materials 0.000 description 4
- 239000011669 selenium Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical group OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- LSIXBBPOJBJQHN-UHFFFAOYSA-N 2,3-Dimethylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C(C)=C(C)C1C2 LSIXBBPOJBJQHN-UHFFFAOYSA-N 0.000 description 1
- HUNDKIPOXXHMOS-UHFFFAOYSA-N 2,4-dinitrofluoren-9-one Chemical compound O=C1C2=CC=CC=C2C2=C1C=C([N+](=O)[O-])C=C2[N+]([O-])=O HUNDKIPOXXHMOS-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 1
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- IICCLYANAQEHCI-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 IICCLYANAQEHCI-UHFFFAOYSA-N 0.000 description 1
- XURABDHWIADCPO-UHFFFAOYSA-N 4-prop-2-enylhepta-1,6-diene Chemical compound C=CCC(CC=C)CC=C XURABDHWIADCPO-UHFFFAOYSA-N 0.000 description 1
- CNGYZEMWVAWWOB-VAWYXSNFSA-N 5-[[4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl]amino]-2-[(e)-2-[4-[[4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound N=1C(NC=2C=C(C(\C=C\C=3C(=CC(NC=4N=C(N=C(NC=5C=CC=CC=5)N=4)N(CCO)CCO)=CC=3)S(O)(=O)=O)=CC=2)S(O)(=O)=O)=NC(N(CCO)CCO)=NC=1NC1=CC=CC=C1 CNGYZEMWVAWWOB-VAWYXSNFSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- IWTYTFSSTWXZFU-QPJJXVBHSA-N [(e)-3-chloroprop-1-enyl]benzene Chemical compound ClC\C=C\C1=CC=CC=C1 IWTYTFSSTWXZFU-QPJJXVBHSA-N 0.000 description 1
- AWKOMEXJXBINBQ-DHZHZOJOSA-N [(e)-3-diethoxyphosphorylprop-1-enyl]benzene Chemical compound CCOP(=O)(OCC)C\C=C\C1=CC=CC=C1 AWKOMEXJXBINBQ-DHZHZOJOSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- MRQIXHXHHPWVIL-UHFFFAOYSA-N chembl1397023 Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC1=CC=CC=C1 MRQIXHXHHPWVIL-UHFFFAOYSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- IINNWAYUJNWZRM-UHFFFAOYSA-L erythrosin B Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 IINNWAYUJNWZRM-UHFFFAOYSA-L 0.000 description 1
- 229940011411 erythrosine Drugs 0.000 description 1
- 235000012732 erythrosine Nutrition 0.000 description 1
- 239000004174 erythrosine Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 229940081623 rose bengal Drugs 0.000 description 1
- 229930187593 rose bengal Natural products 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Description
技術分野
本発明は、新規なジスチリル誘導体に関し、電
子写真用の有機光導電性素材及び螢光増白剤等と
して使用することができ、特に電子写真用の有機
光導電性材料として有用な化合物を提供するもの
である。
従来技術
従来、電子写真方式において使用される感光体
の有機光導電性素材としてポリ−Ｎ−ビニルカル
バゾールをはじめ数多くの材料が提案されてい
る。
ここにいう「電子写真方式」とは一般に光導電
性の感光体を、まず暗所で例えばコロナ放電など
により帯電せしめ、ついで露光部のみの電荷を選
択的に放電させることにより静電潜像を得て、こ
の潜像部をトナーなどを用いて現像手段で可視化
して画像を形成するようにした画像形成法の一つ
である。このような電子写真方式における感光体
に要求される基本的な特性としては、(1)暗所にお
いて適当な電位に帯電されること、(2)暗所におけ
る電荷の放電が少ないこと、(3)光照射により速や
かに電荷を放電すること、などが挙げられる。し
かし、従来の光導電性有機材料はこれらの要求を
かならずしも満足していないのが実状である。
一方、セレンや酸化亜鉛は光導電性無機材料と
して知られており、中でもセレンは広く実用に供
されている。しかし、最近電子写真のプロセスの
点から、感光体に対する種々の要求、即ち一例と
して前述の基本的特性に加えて、例えばその形状
についても可とう性のあるベルト状の感光体など
が要求されるようになつてきている。しかしセレ
ンの場合は一般にこのような形状のものに作成す
ることは困難である。
目 的
本発明の目的は上記のような感光体における光
導電性素材の持つ欠点を除去した、特に光導電性
素材として有用なジスチリル誘導体を提供するこ
とである。
構 成
本発明は、一般式（）
（式中、R1は低級アルキル基、ベンジル基また
は無置換若しくは低級アルキル基、低級アルコキ
シ基または塩素置換のフエニル基を、R2はベン
ジル基または無置換若しくは低級アルコキシ基ま
たは塩素置換のフエニル基を表わす。）
で示されるジスチリル誘導体である。
本発明の化合物を合成するには、一般式（）
［式中、Ｙは
Technical Field The present invention relates to a novel distyryl derivative, which can be used as an organic photoconductive material for electrophotography, a fluorescent brightener, etc., and is particularly useful as an organic photoconductive material for electrophotography. This is what we provide. Prior Art Conventionally, many materials including poly-N-vinylcarbazole have been proposed as organic photoconductive materials for photoreceptors used in electrophotography. The "electrophotographic method" referred to here generally means that a photoconductive photoreceptor is first charged in a dark place by, for example, corona discharge, and then the electrostatic latent image is formed by selectively discharging the charge only in the exposed areas. This is one of the image forming methods in which an image is formed by visualizing this latent image portion using a developing means using toner or the like. The basic characteristics required of a photoreceptor in such an electrophotographic method are (1) to be charged to an appropriate potential in a dark place, (2) to have little discharge of charge in a dark place, and (3) to be charged to an appropriate potential in a dark place. ) Promptly discharging charges by light irradiation. However, the reality is that conventional photoconductive organic materials do not necessarily satisfy these requirements. On the other hand, selenium and zinc oxide are known as photoconductive inorganic materials, and among them selenium is widely used in practical use. However, in recent years, various requirements have been placed on photoreceptors in terms of the electrophotographic process. For example, in addition to the above-mentioned basic characteristics, for example, a belt-like photoreceptor that is flexible in shape is also required. It's starting to look like this. However, in the case of selenium, it is generally difficult to form it into such a shape. Purpose An object of the present invention is to provide a distyryl derivative that is particularly useful as a photoconductive material, which eliminates the above-mentioned drawbacks of photoconductive materials for photoreceptors. Structure The present invention is based on the general formula () (In the formula, R 1 is a lower alkyl group, a benzyl group, an unsubstituted or lower alkyl group, a lower alkoxy group, or a chlorine-substituted phenyl group, and R 2 is a benzyl group, an unsubstituted or lower alkoxy group, or a chlorine-substituted phenyl group. ) is a distyryl derivative represented by To synthesize the compounds of the present invention, the general formula () [In the formula, Y is
【式】（ここで
Ｚ
はハロゲンイオンを示す）で表わされるトル
フエニルスルホニウム基、又は−PO（OR）2
（ここでＲは低級アルキル基を示す）で表わされ
るジアルキル亜燐酸基である。］
で表わされるフエニル誘導体と、下記一般式
（）
（式中、R1は低級アルキル基、ベンジル基、ま
たは無置換若しくは低級アルキル基、低級アルコ
キシ基、または塩素置換のフエニル基を表わし、
R2はベンジル基または無置換若しくは低級アル
コキシ基または塩素置換のフエニル基を表わす。）
で表わされるアルデヒド化合物とを反応されるこ
とによつて得ることができる。
上記の一般式（）で表わされるフエニル誘導
体は対応するハロメチル化合物と亜リン酸トリア
ルキル又はトリフエニルホスフインとを直接ある
いはトルエン、テトラハイドロフラン、Ｎ，Ｎ−
ジメチルホルムアミドなどの溶媒中で加熱するこ
とにより容易に合成される。ここで亜リン酸トリ
アルキルとしては炭素数１〜４のアルキル基、特
にメチル基、エチル基が好ましい。
こうして得られた一般式（）で表わされるフ
エニル誘導体と一般式（）で表わされるアルデ
ヒド化合物とを塩基性触媒の存在下、室温から
100℃程度の温度において反応させる。
塩基性触媒としては苛性ソーダ、苛性カリ、ナ
トリウムアミド水素化ナトリウム及びナトリウム
メチラート、カリウム−ｔ−ブトキサイドなどの
アルコラートを挙げることができる。また反応溶
媒としては、メタノール、エタノール、イソプロ
パノール、ブタノール、２−メトキシエタノー
ル、１，２−ジメトキシエタン、ビス（２−メト
キシエチル）エーテル、ジオキサン、テトラヒド
ロフラン、トルエン、キシレン、ジメチルスルホ
キシド、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ−メ
チルピロリドン、１，３−ジメチル−２−イミダ
ゾリジノンなどを挙げることができる。中でも極
性溶媒、例えばＮ，Ｎ−ジメチルホルムアミド、
及びジメチルスルホキシドが好適である。
反応温度は(1)使用する溶媒の塩基性触媒に対す
る安定性、(2)縮合成分（一般式（）及び（）
の化合物）の反応性、(3)前記塩基性触媒中におけ
る縮合剤としての反応性によつて広範囲に選択す
ることができる。例えば極性溶媒を用いるときは
実際には室温から100℃好ましくは室温から80℃
である。しかし反応時間の短縮又は活性の低い縮
合剤を使用するときはさらに高い温度でもよい。
このようにして得られる本発明の新規なジスチ
リル誘導体を例示すれば次の通りである。
本発明に係わる新規なジスチリル誘導体は、電
子写真用感光体に於ける光導電性素材として極め
て有用であり、染料やルイス酸などの増感剤によ
つて光学的あるいは化学的に増感される。また有
機顔料あるいは無機顔料を電荷発生物質とするい
わゆる機能分離型感光体に於ける電荷移動物質と
してとりわけ有用である。
上記増感剤の例としては、メチルバイオレツ
ト、クリスタルバイオレツト等のトリアリルメタ
ン染料、ローズベンガル、エリスロシン、ローダ
ミンＢ等のサンテン染料、メチレンブルー等のア
ジン染料、２，４，７−トリニトロ−９−フルオ
レノン、２，４−ジニトロ−９−フルオレノン等
のリユイス酸が挙げるれる。
また有機顔料の例としては、シーアイピグメン
トブルー25（CI No.21180）、シーアイピグメント
レツド41（CI No.21200）、シーアイベーシツクレ
ツド３（CI No.45210）等のアゾ系顔料、シーア
イピグメントブルー16（CI No.74100）等のフタ
ロシアニン系顔料、シーアイバツトブラウン５
（CI No.73410）、シーアイバイオレツトダイ（CI
No.73030）等のインジゴ系顔料、アルゴスカー
レツトＢ、インダンスレンスカーレツトＲ等のペ
リレン等顔料が挙げられる。又、セレン、セレン
−テルル、硫化カドミウム、α−シリコン等の無
機材料も使用できる。
次に実施例により本発明を更に詳細に説明す
る。
実施例 １
トランス シンナミルホスホン酸ジエチル
5.09ｇ（0.02モル）と、４−Ｎ，Ｎ−ジフエニル
アミノベンズアルデヒド 5.47ｇ（0.02モル）と
をＮ，Ｎ−ジメチルホルムアミド40mlに溶解し、
これにナトリウムメトキシドの28％メタノール溶
液4.63ｇを27〜35℃で40分を要して滴下した。滴
下後、室温で３時間攪拌を行ない、60mlのメタノ
ールで希釈し結晶を濾取、水洗、乾燥し黄色結晶
6.20ｇ（収率83.0％）を得た。融点は157.5〜
159.0℃であつた。
次いで、ジオキサン／エタノールの混合溶媒か
ら再結晶し、黄色針状結晶、融点158.5〜160.5℃
の１−フエニル−４−（４−Ｎ，Ｎ−ジフエニル
アミノフエニル）−１，３−ブタジエンの純品を
得た。
元素分析値は、
Ｃ％ Ｈ％ Ｎ％
C28H23Nとしての計算値 90.03 6.22 3.75
実測値 90.16 6.22 3.84
赤外線吸収スペクトル（KBr錠剤法）を図に
示したが、985cmにトランスのCH＝面外変角振
動に基づく吸収帯が認められた。
実施例 ２
トランス トリフエニルホスホニウムシンナミ
ルクロライド8.30ｇ（0.02モル）と、４−Ｎ，Ｎ
−ジフエニルアミノベンズアルデヒド5.47ｇ
（0.02モル）とをＮ，Ｎ−ジメチルホルムアミド
40mlに溶解し、これにナトリウムメトキシドの28
％メタノール溶液4.63ｇを25〜30℃で30分を要し
て滴下した。滴下後、室温で４時間攪拌を行な
い、40mlの水で希釈した。生成物を水洗、次いで
メタノールで洗浄後、乾燥した。
次いで、微量のヨウ素と共にトルエン／ｎ−ヘ
キサン混合溶楳から再結晶し、黄色針状結晶、融
点157.5〜159.5℃の１−フエニル−４−（４−Ｎ，
Ｎ−ジフエニルアミノフエニル）−１，３−ブタ
ジエンの純品5.08ｇ（収率68.0％）を得た。
元素分析値は、
Ｃ％ Ｈ％ Ｎ％
C28H23Nとしての計算値 90.03 6.22 3.75
実測値 90.12 6.19 3.82
赤外線吸収スペクトル（KBr錠剤法）は実施
例１のものと一致した。
実施例 ３〜８
実施例１において、４−Ｎ，Ｎ−ジフエニルア
ミノベンズアルデヒドに代え下記表１に示すアル
デヒドを用いる他は実施例１と同様に操作し、新
規なジスチリル誘導体を得た。結果を表２に示
す。A tolphenylsulfonium group represented by the formula: (wherein Z represents a halogen ion) or a dialkyl phosphite group represented by -PO(OR) 2 (wherein R represents a lower alkyl group). ] A phenyl derivative represented by the following general formula () (In the formula, R 1 represents a lower alkyl group, a benzyl group, an unsubstituted or lower alkyl group, a lower alkoxy group, or a chlorine-substituted phenyl group,
R 2 represents a benzyl group, an unsubstituted or lower alkoxy group, or a chlorine-substituted phenyl group. ) can be obtained by reacting with an aldehyde compound represented by The phenyl derivative represented by the above general formula () can be prepared by directly combining the corresponding halomethyl compound with trialkyl phosphite or triphenylphosphine, or using toluene, tetrahydrofuran, N,N-
It is easily synthesized by heating in a solvent such as dimethylformamide. Here, the trialkyl phosphite is preferably an alkyl group having 1 to 4 carbon atoms, particularly a methyl group or an ethyl group. The phenyl derivative represented by the general formula () obtained in this way and the aldehyde compound represented by the general formula () are mixed at room temperature in the presence of a basic catalyst.
The reaction is carried out at a temperature of approximately 100℃. As basic catalysts, mention may be made of caustic soda, caustic potash, sodium amide sodium hydride and alcoholates such as sodium methylate and potassium t-butoxide. In addition, reaction solvents include methanol, ethanol, isopropanol, butanol, 2-methoxyethanol, 1,2-dimethoxyethane, bis(2-methoxyethyl) ether, dioxane, tetrahydrofuran, toluene, xylene, dimethyl sulfoxide, N,N- Dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone and the like can be mentioned. Among them, polar solvents such as N,N-dimethylformamide,
and dimethyl sulfoxide are preferred. The reaction temperature depends on (1) the stability of the solvent used against basic catalysts, (2) the condensation components (general formulas () and ()
(3) Reactivity as a condensing agent in the basic catalyst can be selected from a wide range. For example, when using a polar solvent, the temperature should actually be between room temperature and 100°C, preferably between room temperature and 80°C.
It is. However, higher temperatures may be used if the reaction time is shortened or a less active condensing agent is used. Examples of the novel distyryl derivatives of the present invention thus obtained are as follows. The novel distyryl derivative according to the present invention is extremely useful as a photoconductive material in electrophotographic photoreceptors, and can be optically or chemically sensitized with a sensitizer such as a dye or a Lewis acid. . It is also particularly useful as a charge transfer material in so-called functionally separated photoreceptors that use organic pigments or inorganic pigments as charge generating materials. Examples of the above-mentioned sensitizers include triallylmethane dyes such as methyl violet and crystal violet, Santen dyes such as rose bengal, erythrosine, and rhodamine B, azine dyes such as methylene blue, and 2,4,7-trinitro-9. - Fluorenone, 2,4-dinitro-9-fluorenone, and other Ruyuis acids. Examples of organic pigments include azo pigments such as CI Pigment Blue 25 (CI No. 21180), CI Pigment Red 41 (CI No. 21200), and CI Basic Cred 3 (CI No. 45210); Phthalocyanine pigments such as Blue 16 (CI No. 74100), Sea Butt Brown 5
(CI No.73410), CI Violet Dye (CI
Examples include indigo pigments such as No. 73030) and perylene pigments such as Argo Scarlet B and Indane Scarlet R. Inorganic materials such as selenium, selenium-tellurium, cadmium sulfide, and α-silicon can also be used. Next, the present invention will be explained in more detail with reference to Examples. Example 1 Diethyl trans-cinnamylphosphonate
5.09 g (0.02 mol) and 5.47 g (0.02 mol) of 4-N,N-diphenylaminobenzaldehyde were dissolved in 40 ml of N,N-dimethylformamide,
To this, 4.63 g of a 28% methanol solution of sodium methoxide was added dropwise at 27 to 35°C over 40 minutes. After dropping, stir at room temperature for 3 hours, dilute with 60ml of methanol, collect crystals by filtration, wash with water, and dry to obtain yellow crystals.
6.20g (yield 83.0%) was obtained. Melting point is 157.5 ~
It was 159.0℃. Then, it was recrystallized from a mixed solvent of dioxane/ethanol to give yellow needle-like crystals, melting point 158.5-160.5℃.
A pure product of 1-phenyl-4-(4-N,N-diphenylaminophenyl)-1,3-butadiene was obtained. The elemental analysis values are: C% H% N% C 28 H 23 Calculated value as N 90.03 6.22 3.75 Actual value 90.16 6.22 3.84 The infrared absorption spectrum (KBr tablet method) is shown in the figure, and the CH= plane of the transformer is shown at 985 cm. An absorption band based on external bending vibration was observed. Example 2 8.30 g (0.02 mol) of trans triphenylphosphonium cinnamyl chloride and 4-N,N
- Diphenylaminobenzaldehyde 5.47g
(0.02 mol) and N,N-dimethylformamide
of sodium methoxide dissolved in 40 ml of this
% methanol solution was added dropwise at 25 to 30°C over 30 minutes. After the dropwise addition, the mixture was stirred at room temperature for 4 hours and diluted with 40 ml of water. The product was washed with water, then with methanol, and then dried. Next, it was recrystallized from a toluene/n-hexane mixture with a trace amount of iodine to give 1-phenyl-4-(4-N,
5.08 g (yield 68.0%) of pure N-diphenylaminophenyl-1,3-butadiene was obtained. The elemental analysis values were: C% H% N% Calculated value as C 28 H 23 N 90.03 6.22 3.75 Actual value 90.12 6.19 3.82 The infrared absorption spectrum (KBr tablet method) was consistent with that of Example 1. Examples 3 to 8 New distyryl derivatives were obtained in the same manner as in Example 1, except that the aldehydes shown in Table 1 below were used in place of 4-N,N-diphenylaminobenzaldehyde. The results are shown in Table 2.
【表】【table】
【表】
効 果
以上の説明から明らかなように、本発明に係わ
るジスチリル誘導体は新規な化合物であつて、特
に電子写真用の有機光導性材料として有効なもの
である。[Table] Effects As is clear from the above explanation, the distyryl derivative according to the present invention is a novel compound, and is particularly effective as an organic photoconductive material for electrophotography.
図は、１−フエニル−４−（４−Ｎ，Ｎ−ジフ
エニルアミノフエニル）−１，３−ブタジエンの
赤外吸収スペクトル図である。
The figure is an infrared absorption spectrum diagram of 1-phenyl-4-(4-N,N-diphenylaminophenyl)-1,3-butadiene.
Claims (1)
は、無置換若しくは低級アルキル基、低級アルコ
キシ基または塩素置換のフエニル基を表わし、
R2はベンジル基または、無置換若しくは低級ア
ルコキシ基または塩素置換のフエニル基を表わ
す。） で示されるジスチリル誘導体。[Claims] 1 General formula () (In the formula, R 1 represents a lower alkyl group, a benzyl group, an unsubstituted or lower alkyl group, a lower alkoxy group, or a chlorine-substituted phenyl group,
R 2 represents a benzyl group, an unsubstituted or lower alkoxy group, or a chlorine-substituted phenyl group. ) A distyryl derivative represented by
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6452883A JPS59190931A (en) | 1983-04-14 | 1983-04-14 | Distyryl derivative and its preparation |
| US06/595,022 US4515883A (en) | 1983-04-14 | 1984-03-30 | Stilbene derivatives, distyryl derivatives and electrophotographic photoconductor comprising at least one of the derivatives |
| DE19843414141 DE3414141A1 (en) | 1983-04-14 | 1984-04-14 | STILB DERIVATIVES, DISTYRYL DERIVATIVES AND ELECTROPHOTOGRAPHIC PHOTO LADDERS, WHICH CONTAIN AT LEAST ONE OF THE DERIVATIVES |
| GB08409813A GB2138001B (en) | 1983-04-14 | 1984-04-16 | Stilbene and distyryl derivatives and electrophotographic photoconductors containing them |
| US06/704,675 US4709096A (en) | 1983-04-14 | 1985-02-22 | Stilbene derivatives, distyryl derivatives and electrophotographic photoconductor comprising at least one of the derivatives |
| GB08623489A GB2179942B (en) | 1983-04-14 | 1986-09-30 | Distyryl derivatives and electrophotographic photoconductors containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6452883A JPS59190931A (en) | 1983-04-14 | 1983-04-14 | Distyryl derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59190931A JPS59190931A (en) | 1984-10-29 |
| JPH0547533B2 true JPH0547533B2 (en) | 1993-07-19 |
Family
ID=13260808
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6452883A Granted JPS59190931A (en) | 1983-04-14 | 1983-04-14 | Distyryl derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59190931A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005289842A (en) * | 2004-03-31 | 2005-10-20 | Hodogaya Chem Co Ltd | Method for purifying electronic article material |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6769408B2 (en) * | 2017-07-21 | 2020-10-14 | 京セラドキュメントソリューションズ株式会社 | Electrophotographic photosensitive member, process cartridge, and image forming apparatus |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49104921A (en) * | 1973-01-12 | 1974-10-04 | ||
| US3997342A (en) * | 1975-10-08 | 1976-12-14 | Eastman Kodak Company | Photoconductive element exhibiting persistent conductivity |
-
1983
- 1983-04-14 JP JP6452883A patent/JPS59190931A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49104921A (en) * | 1973-01-12 | 1974-10-04 | ||
| US3997342A (en) * | 1975-10-08 | 1976-12-14 | Eastman Kodak Company | Photoconductive element exhibiting persistent conductivity |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005289842A (en) * | 2004-03-31 | 2005-10-20 | Hodogaya Chem Co Ltd | Method for purifying electronic article material |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59190931A (en) | 1984-10-29 |
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