JPH0513941B2 - - Google Patents
Info
- Publication number
- JPH0513941B2 JPH0513941B2 JP58069202A JP6920283A JPH0513941B2 JP H0513941 B2 JPH0513941 B2 JP H0513941B2 JP 58069202 A JP58069202 A JP 58069202A JP 6920283 A JP6920283 A JP 6920283A JP H0513941 B2 JPH0513941 B2 JP H0513941B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- general formula
- photoconductive
- selenium
- 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
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000000463 material Substances 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 108091008695 photoreceptors Proteins 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- -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
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-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
- 239000000975 dye Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 229910052711 selenium Inorganic materials 0.000 description 4
- 239000011669 selenium Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 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
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
- 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
- 239000013078 crystal Substances 0.000 description 2
- 238000007599 discharging Methods 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
- 239000012860 organic pigment Substances 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000009257 reactivity Effects 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BIKDOQRECXQNQR-UHFFFAOYSA-N (4-chlorophenyl)methylphosphanium;chloride Chemical compound [Cl-].[PH3+]CC1=CC=C(Cl)C=C1 BIKDOQRECXQNQR-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- VHQGURIJMFPBKS-UHFFFAOYSA-N 2,4,7-trinitrofluoren-9-one Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C2C3=CC=C([N+](=O)[O-])C=C3C(=O)C2=C1 VHQGURIJMFPBKS-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
- 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
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052980 cadmium sulfide 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
- 239000000460 chlorine 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
- 238000000921 elemental analysis Methods 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
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 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
- 229910052757 nitrogen Inorganic materials 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
- 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 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
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Photoreceptors In Electrophotography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
技術分野
本発明は新規なスチルベン誘導体に関し、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材料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た現像手段で可視化
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、即わち一例
として前述の基本的特性に加えて、例えばその形
状についても可撓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
素材として有用な新規なスチルベン誘導体を提供
することである。
構 成
本発明は、一般式（）
（式中、Ｘは塩素原子、R1は低級アルキル基
又はベンジル基、R2はベンジル基又はフエニル
基を表わす。）
で示されるスチルベン誘導体である。
かかるスチルベン誘導体は、一般式（）
［式中、Ｘはハロゲン原子、Ｙは
TECHNICAL FIELD The present invention relates to a novel stilbene derivative, which can be used as an organic photoconductive material and a fluorescent brightener for electrophotography, and provides a material that is particularly useful as an organic photoconductive material for electrophotography. It is something. 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 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 able to withstand light irradiation. Examples include discharging charges more quickly. 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, recently, in terms of the electrophotographic process, various demands have been placed on the photoreceptor. For example, in addition to the above-mentioned basic characteristics, there is also a demand for a flexible belt-like photoreceptor in terms of shape. However, in the case of selenium, it is generally difficult to create such shapes. Purpose An object of the present invention is to provide a novel stilbene 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, X represents a chlorine atom, R 1 represents a lower alkyl group or a benzyl group, and R 2 represents a benzyl group or a phenyl group.) Such stilbene derivatives have the general formula () [In the formula, X is a halogen atom, Y is
【式】（ここでＺ
はハロゲ
ンイオンを示す）で表わされるトリフエニルホス
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は低級アルキル基又はベンジル基、
R2はベンジル基又は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せるこ
とによつて得られる。
前記一般式（）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
により容易に製造される。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。又、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更に高い温度でも
よい。このようにして得られる本発明にかかわる
新規なスチルベン誘導体を例示すれば次の通りで
ある。
本発明にかかわる新規なスチルベン誘導体は、
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。又有
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。
上記増感剤として例えば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−フルオレノン等が挙
げられる。
又、有機顔料としてはシーアイピグメントブル
ー25（CI No.21180）、シ−アイピグメントレツド
41（CI No.21200）、シーアイベ−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、インタンスレンスカーレツトＲ等のペリレ
ン系顔料が挙げられる。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
４−クロルベンジルホスホニウムクロライド
42.3ｇ（0.1モル）と、４−Ｎ，Ｎ−ジベンジル
アミノベンズアルデヒド30.1ｇ（0.1モル）をＮ，
Ｎ−ジメチルホルムアミド150mlに溶解し、これ
に28％ナトリウムメチラート、メタノール溶液
28.9ｇ（0.15モル）を25〜30℃で30分を要して滴
下した。添加後、２時間室温で攪拌を行つた後、
反応混合物を水300mlで希釈した。析出し粉末を
濾別、水洗、乾燥後、淡黄色の粉末を得た。収量
は37.8ｇ（収率92.0％）で、融点は137.0〜139.0
℃であつた。
微量のヨウ素と共にトルエン−ｎ−ヘキサンの
混合溶媒から再結晶して淡黄色の針状結晶４−ク
ロル−4′−Ｎ，Ｎ−ジベンジルアミノスチルベン
を得た。収量は33.4ｇ（収率81.5％）で、融点は
150.8〜151.6℃であつた。
元素分析値
Ｃ％ Ｈ％ Ｎ％ Cl％
実測値 82.16 5.84 3.46 8.49
C28H24NClとしての計算値
82.03 5.90 3.42 8.65
実施例 ２〜６
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のかわりに下記表−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、新規なスチルベン誘導体を得た。結果を表−
２に示す。A triphenylphosphonium group represented by [Formula] (wherein Z represents a halogen ion) or a dialkylphosphorous acid group represented by -PO(OR) 2 (herein, R represents a lower alkyl group)] The phenyl derivative represented by the following general formula () (In the formula, R 1 is a lower alkyl group or a benzyl group,
R 2 represents a benzyl group or a phenyl group. ) can be obtained by reacting with an aldehyde compound represented by: The phenyl derivative represented by the general formula () can be obtained by heating the corresponding halomethyl compound and trialkyl phosphite or triphenylphosphine directly or in a solvent such as toluene, tetrahydrofuran, or N,N-dimethylformamide. easily manufactured by 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 () thus obtained 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, as a reaction solvent, 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 etc. 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 the basic catalyst, 2) the reactivity of the condensation components (compounds of general formulas () and ()), and 3) the reactivity as a condensing agent in the basic catalyst. Therefore, a wide range of choices can be made. For example, when using a polar solvent, the temperature is actually room temperature to 100°C, preferably room temperature to 80°C. However, when the reaction time is shortened or a less active condensing agent is used, higher temperatures may be used. Examples of novel stilbene derivatives according to the present invention obtained in this way are as follows. The novel stilbene derivative according to the present invention is
It is extremely useful as a photoconductive material in electrophotographic photoreceptors, and can be sensitized optically or chemically with sensitizers such as dyes and Lewis acids. 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 generation materials. Examples of the sensitizer include methyl violet,
Triallylmethane dyes such as crystal violet, Santen dyes such as rose bengal, erythrosine, and rhodamine B, azine dyes such as methylene blue, 2,4,7-trinitro-9-fluorenone, 2,4-dinitro-9-fluorenone, etc. can be mentioned. In addition, as organic pigments, CI Pigment Blue 25 (CI No. 21180), CI Pigment Red
41 (CI No.21200), CI Base Cred 3
(CI No. 45210), phthalocyanine pigments such as CI Pigment Blue 16 (CI No. 74100), CI Butt Brown 5 (CI No.
73410), CI Violet Dye (CI No.
73030), and perylene pigments such as Argo Scarlet B and Instance 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 4-chlorobenzylphosphonium chloride
42.3 g (0.1 mol) and 30.1 g (0.1 mol) of 4-N,N-dibenzylaminobenzaldehyde in N,
Dissolve in 150 ml of N-dimethylformamide, add 28% sodium methylate, methanol solution
28.9 g (0.15 mol) was added dropwise at 25 to 30°C over 30 minutes. After addition, after stirring at room temperature for 2 hours,
The reaction mixture was diluted with 300ml of water. The precipitated powder was separated by filtration, washed with water, and dried to obtain a pale yellow powder. Yield: 37.8g (yield 92.0%), melting point: 137.0-139.0
It was warm at ℃. Recrystallization from a mixed solvent of toluene-n-hexane with a trace amount of iodine gave pale yellow needle-like crystals of 4-chloro-4'-N,N-dibenzylaminostilbene. The yield was 33.4g (yield 81.5%), and the melting point was
The temperature was 150.8-151.6°C. Elemental analysis value C% H% N% Cl% Actual value 82.16 5.84 3.46 8.49 C 28 H 24 Calculated value as NCl 82.03 5.90 3.42 8.65 Examples 2 to 6 In Example 1, 4-N,N-diphenylaminobenzaldehyde A novel stilbene derivative was obtained in the same manner as in Example 1, except that aldehydes shown in Table 1 below were used instead. Display the results -
Shown in 2.
【表】【table】
【表】
効 果
以上の説明から明らかなように、本発明に係る
スチルベン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電性材料として有効なもの
である。[Table] Effects As is clear from the above explanation, the stilbene derivative according to the present invention is a new compound and is particularly effective as an organic photoconductive material for electrophotography.
図は４−クロル−4′−Ｎ，Ｎ−ジベンジルアミ
ノスチルベンの赤外線吸収スペクトル図である。
The figure is an infrared absorption spectrum diagram of 4-chloro-4'-N,N-dibenzylaminostilbene.
Claims (1)
又はベンジル基、R2はベンジル基又はフエニル
基を表わす。） で示されるスチルベン誘導体。[Claims] 1 General formula () (In the formula, X represents a chlorine atom, R 1 represents a lower alkyl group or a benzyl group, and R 2 represents a benzyl group or a phenyl group.) A stilbene derivative represented by the formula:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58069202A JPS59196845A (en) | 1983-04-21 | 1983-04-21 | Stilbene derivative and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58069202A JPS59196845A (en) | 1983-04-21 | 1983-04-21 | Stilbene derivative and its preparation |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4105090A Division JPH02243657A (en) | 1990-02-23 | 1990-02-23 | Stilbene derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59196845A JPS59196845A (en) | 1984-11-08 |
| JPH0513941B2 true JPH0513941B2 (en) | 1993-02-23 |
Family
ID=13395900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58069202A Granted JPS59196845A (en) | 1983-04-21 | 1983-04-21 | Stilbene derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59196845A (en) |
-
1983
- 1983-04-21 JP JP58069202A patent/JPS59196845A/en active Granted
Non-Patent Citations (2)
| Title |
|---|
| ZEITSCHRIFT FUR NATURFORSCHUNG=1980 * |
| ZEITSCHRIFT FUR NATURFORSCHUNG=1981 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59196845A (en) | 1984-11-08 |
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