JPH0436264A - 1,8-diaminopyrene compound - Google Patents
1,8-diaminopyrene compoundInfo
- Publication number
- JPH0436264A JPH0436264A JP13871090A JP13871090A JPH0436264A JP H0436264 A JPH0436264 A JP H0436264A JP 13871090 A JP13871090 A JP 13871090A JP 13871090 A JP13871090 A JP 13871090A JP H0436264 A JPH0436264 A JP H0436264A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- diaminopyrene
- compound
- halogen
- general formula
- 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.)
- Granted
Links
- -1 1,8-diaminopyrene compound Chemical class 0.000 title claims abstract description 13
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 12
- 150000001875 compounds Chemical class 0.000 abstract description 4
- BLYOXQBERINFDU-UHFFFAOYSA-N pyrene-1,8-diamine Chemical compound C1=C2C(N)=CC=C(C=C3)C2=C2C3=CC=C(N)C2=C1 BLYOXQBERINFDU-UHFFFAOYSA-N 0.000 abstract description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 3
- 150000001447 alkali salts Chemical class 0.000 abstract description 3
- 150000005171 halobenzenes Chemical class 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract description 3
- 238000006482 condensation reaction Methods 0.000 abstract description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract description 2
- 239000012433 hydrogen halide Substances 0.000 abstract description 2
- 239000012299 nitrogen atmosphere Substances 0.000 abstract description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 108091008695 photoreceptors Proteins 0.000 description 12
- 238000000034 method Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000049 pigment Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZLFVRXUOSPRRKQ-VHEBQXMUSA-N CI Pigment Red 3 Chemical compound [O-][N+](=O)C1=CC(C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 ZLFVRXUOSPRRKQ-VHEBQXMUSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012860 organic pigment Substances 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- UDHAWRUAECEBHC-UHFFFAOYSA-N 1-iodo-4-methylbenzene Chemical compound CC1=CC=C(I)C=C1 UDHAWRUAECEBHC-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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000004419 Panlite Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000000297 Sandmeyer reaction Methods 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 239000004840 adhesive resin Substances 0.000 description 1
- 229920006223 adhesive resin Polymers 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 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
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process 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
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003921 oil 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
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- JSTHREDTMPIBEX-UHFFFAOYSA-N pyrene-2,7-diamine Chemical class C1=C(N)C=C2C=CC3=CC(N)=CC4=CC=C1C2=C43 JSTHREDTMPIBEX-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 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
- 229930187593 rose bengal Natural products 0.000 description 1
- AZJPTIGZZTZIDR-UHFFFAOYSA-L rose bengal Chemical compound [K+].[K+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 AZJPTIGZZTZIDR-UHFFFAOYSA-L 0.000 description 1
- 229940081623 rose bengal Drugs 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
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 239000001016 thiazine dye Substances 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
Landscapes
- Photoreceptors In Electrophotography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、電子写真用の有機光導電性材料として有用な
、１，８−ジアミノピレン化合物に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to 1,8-diaminopyrene compounds useful as organic photoconductive materials for electrophotography.
従来、電子写真方式において使用される感光体の有機光
導電性素材としては、例えば、ポリ−Ｎ−ビニルカルバ
ゾール、トリフェニルアミン化合物（米国特許第３，１
８０，７３０号）、ベンジジン化合物（米国特許第３，
２６５，４９６．特公昭３９−１１５４６号公報、特開
昭５３−２７０３３号公報）等のような数多くの開業が
なされている。Conventionally, organic photoconductive materials for photoreceptors used in electrophotography include, for example, poly-N-vinylcarbazole and triphenylamine compounds (U.S. Pat. Nos. 3 and 1).
80,730), benzidine compounds (U.S. Pat. No. 3,
265,496. A large number of such businesses have been opened, such as those disclosed in Japanese Patent Publication No. 39-11546 and Japanese Patent Application Laid-Open No. 53-27033.
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、先ず暗所で例えばコロナ放電などにより帯電せ
しめ、次いで画像状露光を行なって露光部の電荷を選択
的に放電させることにより静電潜像を得、更にこの潜像
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。The "electrophotographic method" referred to here generally refers to a method in which a photoconductive photoreceptor is first charged in a dark place by, for example, corona discharge, and then imagewise exposure is performed to selectively discharge the charges in the exposed areas. This is one of the image forming methods in which an electrostatic latent image is obtained, and this latent image portion is visualized by a developing means using toner or the like to form an image. 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.
しかしながら、従来の光導電性有機材料は、これらの要
求を必ずしも満足していないのが実状である。However, the reality is that conventional photoconductive organic materials do not necessarily satisfy these requirements.
一方、ジアミノピレン系化合物としては、Ｎ、Ｎ。On the other hand, examples of diaminopyrene compounds include N and N.
Ｎ’、Ｎ’−テトラフェニル−１，６−ジアミノピレン
化合物が特開昭５５−１４４２５０号公報に開示されて
いるが。A N',N'-tetraphenyl-1,6-diaminopyrene compound is disclosed in JP-A-55-144250.
この化合物は接着樹脂溶液に対してかなり難溶であり、
前記電子写真方式における感光体に要求される諸条件を
満たす良好な感光層を形成するには極めて困難なもので
ある。This compound is quite poorly soluble in adhesive resin solution,
It is extremely difficult to form a good photosensitive layer that satisfies various conditions required for a photoreceptor in the electrophotographic method.
従って、本発明の目的は、基本的な電子写真特性を全て
満足し、光導電性材料として有用な、新規な１，８−ジ
アミノピレン化合物を提供することにある。Therefore, an object of the present invention is to provide a novel 1,8-diaminopyrene compound that satisfies all basic electrophotographic properties and is useful as a photoconductive material.
本発明によれば、下記一般式（Ｉ）
（式中、Ｒ１及びＲ２は、水素原子、アルキル基、アル
コキシ基、ハロゲン原子又は置換若しくは無置換のフェ
ニル基を表わし、各々同一でも異なっていてもよい、）
で表わされる１、８−ジアミノピレン化合物が提供され
る。According to the present invention, the following general formula (I) (wherein R1 and R2 represent a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, or a substituted or unsubstituted phenyl group, and may be the same or different) A 1,8-diaminopyrene compound represented by the following formula is provided.
前記一般式（１）において、Ｒ１及びＲ２のアルキル基
としては、メチル基、エチル基、プロピル基。In the general formula (1), the alkyl groups for R1 and R2 include a methyl group, an ethyl group, and a propyl group.
ブチル基などの低級アルキル基が、またアルコキシ基と
しては、メトキシ基、エトキシ基、プロポキシ基などの
低級アルコキシ基が挙げら九る。ハロゲン原子としては
、フッ素原子、塩素原子、臭素原子等が挙げられる。ま
たフェニル基における置換基としては、低級アルキル基
（例えば、メチル基、エチル基、プロピル基、ブチル基
など）、低級アルコキシ基（例えば、メトキシ基、エト
キシ基、プロポキシ基など）及びハロゲン原子（例えば
臭素、塩素など）が挙げられる。Examples of the alkoxy group include lower alkyl groups such as a butyl group, and lower alkoxy groups such as a methoxy group, an ethoxy group, and a propoxy group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and the like. Substituents on the phenyl group include lower alkyl groups (e.g., methyl, ethyl, propyl, butyl, etc.), lower alkoxy groups (e.g., methoxy, ethoxy, propoxy, etc.), and halogen atoms (e.g., (bromine, chlorine, etc.).
本発明に係る前記一般式（Ｉ）で示される１、８ジアミ
ノピレン化合物は、新規物質であり、このものは、下記
一般式（ＩＩ）で表わされるハロベンゼン誘導体と下記
一般式（ＩＩＩ）で表わされる１、８−ジアミノピレン
又は下記一般式（ＩＶ）で表わされる１、８−ジハロゲ
ノピレンと下記一般式（Ｖ）で表わされるジフェニルア
ミン誘導体及び銅粉、酸化銅あるいはハロゲン化網など
と縮合反応中に生ずるハロゲン化水素を中和するのに充
分な量のアルカリ塩を加え、溶媒の存在下又は無溶媒下
で、窒素雰囲気下、１５０〜２５０℃程度の温度におい
て反応させることにより製造することができる。The 1,8-diaminopyrene compound represented by the general formula (I) according to the present invention is a new substance, and is composed of a halobenzene derivative represented by the following general formula (II) and a halobenzene derivative represented by the following general formula (III). 1,8-diaminopyrene represented by the following general formula (IV) or 1,8-dihalogenopyrene represented by the following general formula (IV) and a diphenylamine derivative represented by the following general formula (V) and copper powder, copper oxide or halogenated network during a condensation reaction. It can be produced by adding a sufficient amount of alkali salt to neutralize the generated hydrogen halide and reacting in the presence of a solvent or in the absence of a solvent at a temperature of about 150 to 250°C under a nitrogen atmosphere. .
この場合、アルカリ塩としては、苛性ソーダ、苛性カリ
ウム、炭酸ナトリウム、炭酸カリウムなどを挙げること
ができる。また、反応溶媒としては、ニトロベンゼン、
ジクロルベンゼン、キノリン、 Ｎ、Ｎ−ジメチルホル
ムアミド、ジメチルスルホキシド、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。In this case, examples of the alkali salt include caustic soda, caustic potassium, sodium carbonate, potassium carbonate, and the like. In addition, as a reaction solvent, nitrobenzene,
Examples include dichlorobenzene, quinoline, N,N-dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, and the like.
（式中、Ｒ１及びＲ２は前記と同じ。Ｘはハロゲン原子
を表わす。）
（式中、Ｘはハロゲン原子を表わす。）（式中、Ｒ１及
びＲ２は前記と同し。）尚、原料である上記式（ＩＩＩ
）で表わされる１、８−ジアミノピレンの合成法はＣｈ
ｅｍ、 Ｐｈａｒｍ、 Ｂｕｌｌ、、 ３２゜１９９２
Ｐ、 １９８４年に記載されており、又、一般式（ＩＶ
）で表わされる１、８−ジハロゲノピレンは上記１，８
−ジアミノピレンをジアゾニウム塩とし、ハロゲンで置
換する所謂ザンドマイヤー（Ｓａｎｄｍｅｙｅｒ）反応
により容易に合成することができる。(In the formula, R1 and R2 are the same as above. X represents a halogen atom.) (In the formula, X represents a halogen atom.) (In the formula, R1 and R2 are the same as above.) Certain of the above formula (III
) is the synthesis method of 1,8-diaminopyrene represented by Ch.
em, Pharm, Bull, 32°1992
P, was described in 1984, and also has the general formula (IV
1,8-dihalogenopyrene represented by
It can be easily synthesized by the so-called Sandmeyer reaction in which -diaminopyrene is converted into a diazonium salt and substituted with a halogen.
本発明で得られる新規な１．８−ジアミノピレン化合物
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って光
学的あるいは化学的に増感される。更にこのものは、有
機顔料あるいは無機顔料を電荷発生物質とする、所謂機
能分離型感光体に於ける電荷輸送物質としてとりわけ有
用である。The novel 1,8-diaminopyrene compound obtained by the present invention is extremely useful as a photoconductive material in electrophotographic photoreceptors, and can be used optically or chemically with sensitizers such as dyes and Lewis acids. Sensitized. Furthermore, this material is particularly useful as a charge transporting material in a so-called functionally separated photoreceptor in which an organic pigment or an inorganic pigment is used as a charge generating material.
上記増感剤としては、例えば、メチルバイオレット、ク
リスタルバイオレット等のトリアリールメタン染料、ロ
ーズベンガル、エリスロシン、ローダミン等のキサンチ
ン染料、メチレンブルー等のチアジン染料、２，４．７
−ドリニトロー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。Examples of the sensitizer include triarylmethane dyes such as methyl violet and crystal violet, xanthine dyes such as rose bengal, erythrosine, and rhodamine, thiazine dyes such as methylene blue, etc.
-Dolinitro-9-fluorenone, 2,4-dinitro-
Examples include 9-fluorenone.
また、有機顔料としてはシーアイピグメントブルー２５
（ＣＩ Ｎα２１１８０）、シーアイピグメントレッド
４１（ＣＩ Ｎα２１２００）、シーアイピグメントレ
ッド３（ＣＩＮ１１４５２１０）等のアゾ系顔料、シー
アイピグメントブルー１６（ＣＩ ＆７４１００）等の
フタロシアニン系顔料、シーアイバットブラウン５（Ｃ
Ｉ ＆７３４１０）、シーアイバットダイ（ＣＩ Ｎα
７３０３０）等のインジゴ系顔料、アルゴスカーレット
Ｂ、インダンスレンスカーレットＲ等のペリレン系顔料
が挙げられる。また、セレン、セレン−テルル、硫化カ
ドミウム、α−シリコン等の無機顔料も使用できる。In addition, as an organic pigment, C.I. Pigment Blue 25
(CI Nα21180), CI Pigment Red 41 (CI Nα21200), azo pigments such as CI Pigment Red 3 (CIN1145210), phthalocyanine pigments such as CI Pigment Blue 16 (CI &74100), CI Butt Brown 5 (C
CI &73410), CI Nα
73030), and perylene pigments such as Argo Scarlet B and Indance Scarlet R. Inorganic pigments such as selenium, selenium-tellurium, cadmium sulfide, and α-silicon can also be used.
本発明に係る前記一般式（Ｉ）で示される新規な１．８
−ジアミノピレン化合物は、前記したように光導電性素
材として有効に機能し、また染料やルイス酸などの増感
剤によって光学的あるいは化学的に増感されることから
、電子写真用感光体の感光層の電荷輸送物質等として好
適に使用され、特に電荷発生層と電荷輸送層を二層に区
分した。所謂機能分離型感光層における電荷輸送物質と
して有用なものである。Novel 1.8 represented by the general formula (I) according to the present invention
- Diaminopyrene compounds function effectively as photoconductive materials as described above, and can be sensitized optically or chemically with sensitizers such as dyes and Lewis acids, so they can be used as photoconductors for electrophotography. It is suitably used as a charge transport material in a photosensitive layer, and is particularly divided into two layers: a charge generation layer and a charge transport layer. It is useful as a charge transport material in a so-called functionally separated photosensitive layer.
以下１本発明を実施例により詳細に説明する。 The present invention will be explained in detail below using examples.
実施例１
１．８−ジアミノピレン０．７０ｇ、４−ヨードトルエ
ン２０．９３ｇ、炭酸カリウム２．４９ｇ及び銅粉０．
１９ｇを窒素気流下、共沸脱水しながら、２０９℃で５
時間撹拌し′た。室温まで放冷した後、セライトを用い
て濾過し、濾液にクロロホルムを加え、クロロホルム層
を水洗し、次いで硫酸マグネシウムで乾燥し、更に減圧
濃縮して、暗褐色油状物を得た。これをシリカゲルカラ
ム処理〔溶離液：トルエン／ｎ−ヘキサン（１：３）混
合溶媒〕し、エタノール／Ｎ、Ｎ−ジメチルホルムアミ
ド混合溶媒から再結晶して、黄色柱状結晶の下式で示さ
れるＮ、Ｎ、Ｎ’ 、Ｎ’−テトラキス（４−゛メチル
フェニル）−１，８−ジアミノピレン０．９２ｇ（収率
５１．７％）を得た。このものの融点は２８０℃であっ
た。Example 1 1.8-diaminopyrene 0.70g, 4-iodotoluene 20.93g, potassium carbonate 2.49g and copper powder 0.
19g was heated at 209℃ for 5 minutes while azeotropically dehydrating it under a nitrogen stream.
Stir for an hour. After cooling to room temperature, the mixture was filtered through Celite, chloroform was added to the filtrate, and the chloroform layer was washed with water, dried over magnesium sulfate, and further concentrated under reduced pressure to obtain a dark brown oil. This was treated with a silica gel column [eluent: toluene/n-hexane (1:3) mixed solvent] and recrystallized from an ethanol/N,N-dimethylformamide mixed solvent. , N, N', N'-tetrakis(4-'methylphenyl)-1,8-diaminopyrene 0.92 g (yield 51.7%) was obtained. The melting point of this product was 280°C.
Ｕち 元素分析値はＣ４４８，ｓＮ２と ０％ 実測値 ８９．１０ 計算値 ８９．１５ して下記の通りであった。Uchi Elemental analysis values are C448, sN2 0% Actual value: 89.10 Calculated value 89.15 It was as follows.
Ｎ％ Ｎ％
６．０５ ４．６０
６．１２ ４．７３
この化合物の赤外吸収スペクトル（ＫＢｒ錠剤法）を第
１図に示す。N% N% 6.05 4.60 6.12 4.73 The infrared absorption spectrum (KBr tablet method) of this compound is shown in FIG.
応用例
電荷発生物質として下記ビスアゾ化合物７．５部及びポ
リエステル樹脂〔■東洋紡績製バイロン２００〕の０．
５％テトラヒドロフラン溶液５００部をボールミル中で
粉砕混合し、得られた分散液をアルミニウム蒸着ポリエ
ステルフィルム上にドクターブレードで塗布し、自然乾
燥して約ＩＨ厚の電荷発生層を形成した。次に、ポリカ
ーボネート樹脂［■今人製パンライトに一１３００］１
部とテトラヒドロフラン８部の樹脂溶液に、電荷輸送物
質として実施例１の化合物１部を溶解し、この溶液を前
記電荷発生層上にドクターブレードで塗布し、８０℃で
２分間。Application Example As a charge generating substance, 7.5 parts of the following bisazo compound and 0.0 parts of polyester resin [■Vylon 200 manufactured by Toyobo Co., Ltd.] were used.
500 parts of a 5% tetrahydrofuran solution was pulverized and mixed in a ball mill, and the resulting dispersion was applied onto an aluminum-deposited polyester film using a doctor blade and air-dried to form a charge generation layer having a thickness of about IH. Next, polycarbonate resin [■Konjin Panlite 11300] 1
1 part of the compound of Example 1 as a charge transport substance was dissolved in a resin solution containing 1 part and 8 parts of tetrahydrofuran, and this solution was applied onto the charge generation layer using a doctor blade at 80°C for 2 minutes.
次いで１２０℃で５分間乾燥して厚さ約２０．の電荷輸
送層を形成して感光体を作成した。Then, it was dried at 120°C for 5 minutes to a thickness of about 20mm. A photoreceptor was prepared by forming a charge transport layer.
次に、こうして得られた積層型電子写真感光体の可視域
での感度を調べるため、この感光体に静電複写紙試験装
置〔■川口電機製作所製５Ｐ４２８型〕を用いて暗所で
一６ＫＶのコロナ放電を２０秒間行なって帯電させた後
、感光体の表面電位ＶＯＩ（Ｖ）を測定し、更に２０秒
間暗所に放置した後１表面型位Ｖｏ（ｖ）を測定した。Next, in order to examine the sensitivity of the laminated electrophotographic photoreceptor thus obtained in the visible range, this photoreceptor was tested at 16 KV in a dark place using an electrostatic copying paper tester [Type 5P428 manufactured by Kawaguchi Electric Manufacturing Co., Ltd.]. After charging the photoreceptor by corona discharge for 20 seconds, the surface potential VOI (V) of the photoreceptor was measured, and after being left in a dark place for another 20 seconds, the surface potential VoI (v) was measured.
次いで、タングステンランプ光を感光体表面での照度が
４．５１ｕｘになるように照射して、Ｖｏが１／２にな
るまでの露光量Ｅｌ／２（４ｕｘ−ｓｅｃ）を測定した
。その結果、ｖＯは−１３２１（Ｖ）またＥｌ ／２は
０．９５（Ｑｕｘｏｓｅｃ）であった。Next, tungsten lamp light was irradiated so that the illuminance on the surface of the photoreceptor was 4.51 ux, and the exposure amount El/2 (4 ux-sec) until Vo became 1/2 was measured. As a result, vO was -1321 (V) and El/2 was 0.95 (Quxosec).
第１図は実施例１で得られた１、８−ジアミノピレン化
合物の赤外線吸収スペクトル図（ＫＢｒＢｒ法）である
。
特許出願人 株式会社 リ゛ コ
代 理 人弁理士池浦敏明
（ほか１名）
手続補正書
ｉ、□１
平成３年す月２／日FIG. 1 is an infrared absorption spectrum diagram (KBrBr method) of the 1,8-diaminopyrene compound obtained in Example 1. Patent applicant Riko Co., Ltd. Agent Toshiaki Ikeura (and 1 other person) Patent attorney Procedural amendment i, □1 Date of April 2, 1991
Claims (1)
アルコキシ基、ハロゲン原子又は置換若しくは無置換の
フェニル基を表わし、各々同一でも異なっていてもよい
、） で表わされる１、８−ジアミノピレン化合物。(1) General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R^1 and R^2 are hydrogen atoms, alkyl groups,
A 1,8-diaminopyrene compound representing an alkoxy group, a halogen atom, or a substituted or unsubstituted phenyl group, each of which may be the same or different.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13871090A JP2849730B2 (en) | 1990-05-29 | 1990-05-29 | 1,8-diaminopyrene compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13871090A JP2849730B2 (en) | 1990-05-29 | 1990-05-29 | 1,8-diaminopyrene compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0436264A true JPH0436264A (en) | 1992-02-06 |
| JP2849730B2 JP2849730B2 (en) | 1999-01-27 |
Family
ID=15228321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13871090A Expired - Fee Related JP2849730B2 (en) | 1990-05-29 | 1990-05-29 | 1,8-diaminopyrene compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2849730B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5344985A (en) * | 1991-12-28 | 1994-09-06 | Ricoh Company, Ltd. | Aldehyde intermediates for the preparation of pyrenylamine derivatives having unsaturated bond |
| US5475137A (en) * | 1991-09-02 | 1995-12-12 | Ricoh Company, Ltd. | M-phenylenediamine derivatives |
| US5672728A (en) * | 1991-12-28 | 1997-09-30 | Ricoh Company, Ltd. | Method for preparing the pyrenylamine derivatives |
| EP1604974A4 (en) * | 2003-03-20 | 2007-11-14 | Idemitsu Kosan Co | Aromatic amine derivative and organic electroluminescent element made with the same |
-
1990
- 1990-05-29 JP JP13871090A patent/JP2849730B2/en not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5475137A (en) * | 1991-09-02 | 1995-12-12 | Ricoh Company, Ltd. | M-phenylenediamine derivatives |
| US5344985A (en) * | 1991-12-28 | 1994-09-06 | Ricoh Company, Ltd. | Aldehyde intermediates for the preparation of pyrenylamine derivatives having unsaturated bond |
| US5672728A (en) * | 1991-12-28 | 1997-09-30 | Ricoh Company, Ltd. | Method for preparing the pyrenylamine derivatives |
| EP1604974A4 (en) * | 2003-03-20 | 2007-11-14 | Idemitsu Kosan Co | Aromatic amine derivative and organic electroluminescent element made with the same |
| US8592051B2 (en) | 2003-03-20 | 2013-11-26 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative and organic electroluminescent element made with the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2849730B2 (en) | 1999-01-27 |
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