JPH0558032B2 - - Google Patents

Info

Publication number: JPH0558032B2
Authority: JP; Japan
Prior art keywords: compound; disazo; photoreceptor; charge; present
Prior art date: 1984-09-26
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

Application number

JP59200995A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6178876A (ja

Inventor

Mitsuru Hashimoto

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ricoh Co Ltd

Original Assignee

Ricoh Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-09-26

Filing date

1984-09-26

Publication date

1993-08-25

1984-09-26 Application filed by Ricoh Co Ltd filed Critical Ricoh Co Ltd

1984-09-26 Priority to JP59200995A priority Critical patent/JPS6178876A/ja

1986-04-22 Publication of JPS6178876A publication Critical patent/JPS6178876A/ja

1993-08-25 Publication of JPH0558032B2 publication Critical patent/JPH0558032B2/ja

Status Granted legal-status Critical Current

Links

-1 disazo compound Chemical class 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000004970 halomethyl group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
108091008695 photoreceptors Proteins 0.000 description 32
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 15
239000010410 layer Substances 0.000 description 15
150000001875 compounds Chemical class 0.000 description 14
238000004519 manufacturing process Methods 0.000 description 14
239000000243 solution Substances 0.000 description 12
238000000034 method Methods 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
150000003839 salts Chemical class 0.000 description 9
230000035945 sensitivity Effects 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000000862 absorption spectrum Methods 0.000 description 6
238000006193 diazotization reaction Methods 0.000 description 6
239000000463 material Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000000049 pigment Substances 0.000 description 4
239000011347 resin Substances 0.000 description 4
229920005989 resin Polymers 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000002800 charge carrier Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
230000003595 spectral effect Effects 0.000 description 3
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 3
235000021286 stilbenes Nutrition 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
OJJHIWJWSXSTNE-UHFFFAOYSA-N 1,2-diaminothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(N)C(N)=CC=C3SC2=C1 OJJHIWJWSXSTNE-UHFFFAOYSA-N 0.000 description 1
JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 description 1
NIZIGUQDQIALBQ-UHFFFAOYSA-N 4-(2,2-diphenylethenyl)-n,n-diphenylaniline Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 NIZIGUQDQIALBQ-UHFFFAOYSA-N 0.000 description 1
229910017008 AsF 6 Inorganic materials 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
239000004419 Panlite Substances 0.000 description 1
229910018286 SbF 6 Inorganic materials 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
230000002238 attenuated effect Effects 0.000 description 1
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
239000011230 binding agent Substances 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
238000001816 cooling Methods 0.000 description 1
238000010586 diagram Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000010419 fine particle Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000005286 illumination Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229920005668 polycarbonate resin Polymers 0.000 description 1
239000004431 polycarbonate resin Substances 0.000 description 1
229920001225 polyester resin Polymers 0.000 description 1
239000004645 polyester resin Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000002356 single layer Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical group C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-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
238000007738 vacuum evaporation Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
- G03G5/0675—Azo dyes
- G03G5/0679—Disazo dyes
- G03G5/0681—Disazo dyes containing hetero rings in the part of the molecule between the azo-groups
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom

Landscapes

Physics & Mathematics (AREA)
Spectroscopy & Molecular Physics (AREA)
General Physics & Mathematics (AREA)
Light Receiving Elements (AREA)
Photoreceptors In Electrophotography (AREA)

JP59200995A 1984-09-26 1984-09-26 ジスアゾ化合物 Granted JPS6178876A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP59200995A JPS6178876A (ja)	1984-09-26	1984-09-26	ジスアゾ化合物

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP59200995A JPS6178876A (ja)	1984-09-26	1984-09-26	ジスアゾ化合物

Publications (2)

Publication Number	Publication Date
JPS6178876A JPS6178876A (ja)	1986-04-22
JPH0558032B2 true JPH0558032B2 (ko)	1993-08-25

Family

ID=16433753

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP59200995A Granted JPS6178876A (ja)	1984-09-26	1984-09-26	ジスアゾ化合物

Country Status (1)

Country	Link
JP (1)	JPS6178876A (ko)

1984
- 1984-09-26 JP JP59200995A patent/JPS6178876A/ja active Granted

Also Published As

Publication number	Publication date
JPS6178876A (ja)	1986-04-22

Legal Events

Date	Code	Title	Description
2004-09-26	EXPY	Cancellation because of completion of term

Publication	Publication Date	Title
JPH0158182B2 (ko)	1989-12-11
JPH0334503B2 (ko)	1991-05-22
JPH0466905B2 (ko)	1992-10-26
JPS5935935B2 (ja)	1984-08-31	新規なジスアゾ化合物およびその製造方法
JPH0753829B2 (ja)	1995-06-07	新規なビスアゾ化合物及びその製造方法
JPH0558032B2 (ko)	1993-08-25
JPH0784565B2 (ja)	1995-09-13	ジスアゾ化合物
JPH0368070B2 (ko)	1991-10-25
JP2906149B2 (ja)	1999-06-14	ビスアゾ化合物及びその製造法
JPH0158180B2 (ko)	1989-12-11
JPH0721116B2 (ja)	1995-03-08	新規なジスアゾ化合物およびその製造方法
JPH0562150B2 (ko)	1993-09-07
JPH0554510B2 (ko)	1993-08-12
JP2504989B2 (ja)	1996-06-05	１，１０−ビス（４−アミノフエニル）−１，３，５，７，９−デカペンタエン及びその製造法
JPH0447714B2 (ko)	1992-08-04
JPH0449585B2 (ko)	1992-08-11
JPH0554509B2 (ko)	1993-08-12
JP2504972B2 (ja)	1996-06-05	１，１２−ビス（４−アミノフエニル）−１，３，５，７，９，１１−ドデカヘキサエン及びその製造法
JPH0723453B2 (ja)	1995-03-15	ジスアゾ化合物
JPH032912B2 (ko)	1991-01-17
JPH0735359B2 (ja)	1995-04-19	新規なテトラゾニウム塩化合物及びその製造方法
JPS60141764A (ja)	1985-07-26	ジスアゾ化合物およびその製造方法
JPH0948757A (ja)	1997-02-18	トリスアゾ化合物
JPH08209007A (ja)	1996-08-13	ビスアゾ化合物及びその製造用の中間体
JPH0819340B2 (ja)	1996-02-28	フエナジン誘導体及びその製造方法