US3909260A - Sensitizer for use in electrophotographic light-sensitive material - Google Patents
Sensitizer for use in electrophotographic light-sensitive material Download PDFInfo
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- US3909260A US3909260A US406267A US40626773A US3909260A US 3909260 A US3909260 A US 3909260A US 406267 A US406267 A US 406267A US 40626773 A US40626773 A US 40626773A US 3909260 A US3909260 A US 3909260A
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- 239000000463 material Substances 0.000 title abstract description 17
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 claims description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical class C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 40
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 28
- 125000000217 alkyl group Chemical group 0.000 abstract description 15
- 125000005843 halogen group Chemical group 0.000 abstract description 15
- 229910052801 chlorine Inorganic materials 0.000 abstract description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 11
- 229910052794 bromium Inorganic materials 0.000 abstract description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
- 125000001424 substituent group Chemical group 0.000 abstract description 6
- 125000002252 acyl group Chemical group 0.000 abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 abstract description 5
- 125000003282 alkyl amino group Chemical group 0.000 abstract description 5
- 125000003277 amino group Chemical group 0.000 abstract description 5
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract description 5
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 3
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 abstract description 2
- 229910001914 chlorine tetroxide Inorganic materials 0.000 abstract 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 abstract 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- -1 chloropropyl Chemical group 0.000 description 37
- 230000015572 biosynthetic process Effects 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 150000001716 carbazoles Chemical class 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 229910052740 iodine Inorganic materials 0.000 description 10
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- MOUWHELOIWNTJL-UHFFFAOYSA-N 1-(6-bromo-9-ethylcarbazol-3-yl)ethanone Chemical compound C(C)(=O)C=1C=CC=2N(C3=CC=C(C=C3C2C1)Br)CC MOUWHELOIWNTJL-UHFFFAOYSA-N 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 150000007517 lewis acids Chemical group 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000002841 Lewis acid Substances 0.000 description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- AAMBQMDRFSEKOF-UHFFFAOYSA-N 1-(9-ethylcarbazol-3-yl)ethanone Chemical compound CC(=O)C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 AAMBQMDRFSEKOF-UHFFFAOYSA-N 0.000 description 3
- 206010034960 Photophobia Diseases 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 208000013469 light sensitivity Diseases 0.000 description 3
- JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000001235 sensitizing effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LQKYIZSKVFAVBV-UHFFFAOYSA-N 1-(6-chloro-9-ethylcarbazol-3-yl)ethanone Chemical compound CC(=O)C1=CC=C2N(CC)C3=CC=C(Cl)C=C3C2=C1 LQKYIZSKVFAVBV-UHFFFAOYSA-N 0.000 description 2
- CNILDPCFXDESRI-UHFFFAOYSA-N 1-(9h-carbazol-3-yl)ethanone Chemical compound C1=CC=C2C3=CC(C(=O)C)=CC=C3NC2=C1 CNILDPCFXDESRI-UHFFFAOYSA-N 0.000 description 2
- URRDEUPGAMOHGQ-UHFFFAOYSA-N 1-[9-(2-chloroethyl)carbazol-3-yl]ethanone Chemical compound C(C)(=O)C=1C=CC=2N(C3=CC=CC=C3C2C1)CCCl URRDEUPGAMOHGQ-UHFFFAOYSA-N 0.000 description 2
- ZNMVDLYGIWGQKY-UHFFFAOYSA-N 1-[9-(2-hydroxyethyl)carbazol-3-yl]ethanone Chemical compound C(C)(=O)C=1C=CC=2N(C3=CC=CC=C3C2C1)CCO ZNMVDLYGIWGQKY-UHFFFAOYSA-N 0.000 description 2
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
- IHFRMUGEILMHNU-UHFFFAOYSA-N 2-hydroxy-5-nitrobenzaldehyde Chemical compound OC1=CC=C([N+]([O-])=O)C=C1C=O IHFRMUGEILMHNU-UHFFFAOYSA-N 0.000 description 2
- MNOXBMJZRYBLAB-UHFFFAOYSA-N 3-(3-acetylcarbazol-9-yl)propanenitrile Chemical compound C(C)(=O)C=1C=CC=2N(C3=CC=CC=C3C2C1)CCC#N MNOXBMJZRYBLAB-UHFFFAOYSA-N 0.000 description 2
- XNRGRDNWHZWEOT-UHFFFAOYSA-N C1=CC=C2C3=CC(C(=O)C)=CC=C3N(C(C)=O)C2=C1 Chemical compound C1=CC=C2C3=CC(C(=O)C)=CC=C3N(C(C)=O)C2=C1 XNRGRDNWHZWEOT-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000005998 bromoethyl group Chemical group 0.000 description 2
- 125000005997 bromomethyl group Chemical group 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 229920005556 chlorobutyl Polymers 0.000 description 2
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000001003 triarylmethane dye Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RMOVJQZTZDJESW-UHFFFAOYSA-N 1-(9-methylcarbazol-3-yl)ethanone Chemical compound C1=CC=C2C3=CC(C(=O)C)=CC=C3N(C)C2=C1 RMOVJQZTZDJESW-UHFFFAOYSA-N 0.000 description 1
- DGPBVJWCIDNDPN-UHFFFAOYSA-N 2-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=CC=C1C=O DGPBVJWCIDNDPN-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- STBGLXMINLWCNL-UHFFFAOYSA-N 3-bromo-2-hydroxybenzaldehyde Chemical compound OC1=C(Br)C=CC=C1C=O STBGLXMINLWCNL-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 241000582541 Cetraspora helvetica Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- AOADSHDCARXSGL-ZMIIQOOPSA-M alkali blue 4B Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC2=CC=CC=C2S([O-])(=O)=O)=C(\C=C2)/C=C/C\2=N\C2=CC=CC=C2)=CC=C1N.[Na+] AOADSHDCARXSGL-ZMIIQOOPSA-M 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- G03G5/0622—Heterocyclic compounds
- G03G5/0644—Heterocyclic compounds containing two or more hetero rings
- G03G5/0661—Heterocyclic compounds containing two or more hetero rings in different ring systems, each system containing at least one hetero ring
Definitions
- ABSTRACT A sensitizer for use in an electrophotographic lightsensitive material containing an organic photoconductor comprising a pyrylium salt containing a carbazole nucleus represented by the following general formula wherein R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having from 1 to 5 carbon atoms a cyanoalkyl group having from 2 to 6 carbon atoms, a hydroxyalkyl group having 1 to 5 carbon atoms, or an acyl group; R represents a hydrogen atom, a halogen atom or a nitro group, R represents R, represents a hydrogen atom or a hydroxy group; or R and R when taken together form a substituted or unsubstituted benzen
- the present invention relates to a sensitizer for use in an electrophotographic light-sensitive material wherein an organic compound is used as a photoconductor.
- polyvinyl hetero ring compounds represented by poly-N-vinyl carbazole; polynuclear aromatic vinyl polymers such as polyvinylanthracene; low molecular weight compounds having a hetero ring such as an oxazole nucleus, a thiazole nucleus, etc.; and the like, have been used heretofore.
- the present invention provides an absolutely novel sensitizer which, when added to an organic photoconductor, improves not only the light sensitivity but also broadens the wavelength region to which the photoconductor is sensitive. More particularly, the present invention provides a sensitizer comprising a pyrylium salt having a carbazole nucleus.
- synthesis of the various pyrylium salts suitably used in the present invention can be by condensing (A) an ohydroxyarylaldehyde and a carbonyl compound or (B) one molecule of an arylaldehyde and two molecules of a carbonyl compound, in an inert solvent, such as a substituted aromatic hydrocarbon, e.g., nitrobenzene, chlorobenzene, etc., referenced in the above-described literature as one convenient process for synthesizing pyrylium salts.
- an inert solvent such as a substituted aromatic hydrocarbon, e.g., nitrobenzene, chlorobenzene, etc.
- the various pyrylium salts can be synthesized by the above-described reaction (A) using an ohydroxyarylaldehyde represented by the following general formula (III) and a carbonyl group-containing carbazole derivative represented by the following general formula (II), or by the above described reaction (B) using a carbonyl group containing carbazole derivative represented by the following general formula (II) and an arylaldehyde represented by the following general formula (IV).
- Reactions (A) and (B) are schematically described below:
- the reactants are generally used in an equimolar ratio and the reaction is conducted in an inert solvent such as an ester (e.g., ethyl acetate, propyl acetate, butyl acetate, etc.; a cyclic ether (e.g., tetrahydrofuran, etc.) and the like.
- a suitable temperature is from about 1 C to 20C, preferably C to C with reaction times of about 5 minutes to 10 hours, more generally 10 minutes to 1 hour.
- a Lewis acid such as HCl, HBr and H1 is generally present during the reaction.
- reaction (A) represents a hydrogen atom or and R represents a hydrogen atom, a halogen atom (such as a chlorine atom, a bromine atom, an iodine atom or a florine atom), an alkyl group having 1 to 5 carbon atoms (such as methyl, ethyl, propyl, butyl or pentyl), an amino group or an alkylamino group having 1 to 4 carbon atoms (such as ethylamino, methyl amino, propylamino, dimethylamino diethylamino and the like); and Lewis acid represents HCl, HBr, HCIO HNO H 80 BP or BF (C H O; and X represents a Lewis acid residue such as Cl, Br, 1", C10 N0 l-lSOf, or
- HX such as HCl, HBr, HClO HNO H 50 BF or BF ,(C H O wherein X represents a Lewis acid residue such as Cl, Br, C10 N0 H50 or BF ⁇
- HX represents a Lewis acid residue such as Cl, Br, C10 N0 H50 or BF ⁇
- the inventors have experimentally confirmed that, when a hydrogen atom is in the 6-position a triarylmethane dye will be formed under the same reaction conditions.
- R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms (such as methyl, ethyl, propyl, butyl or pentyl), an haloalkyl group having 1 to 5 carbon atoms (such as chloromethyl, chloro-ethyl, chloropropyl, dichloropropyl, chlorobutyl, bromomethyl, bromoethyl, iodomethyl, iodoethyl, fluoromethyl, fluoroethyl, and the like), a cyanoalkyl group having 2 to 6 carbon atoms (such as cyanomethyl, cyanoethyl, cyanopropyl, cyanobutyl, cyanopentyl, and the like), a hydroxyalkyl group having 1 to 5 carbon atoms (such as hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxy
- R represents a hydrogen atom, a halogen atom (such asxachlorine atom, a
- Rgrepresents R represents a hydrogen atom, a halogen atom (such as a chlorine atom, a bromine atom, iodine atom or a florine atom) or an amino group or an alkylamino group having 1 to 4 carbon atoms (such as ethyl amino, methyl amino, propylamino, dimethylamino, diethylamino and the like),'an alkyl group'having l to 5 carbon atoms (such as methyl, ethyl, propyl, butyl or pentyl); and X represents Cl, Br, I, C10 N H80 or BF Preferred substituents for the pyrylium salts of this invention are for R a methyl group, an ethyl group or a hydrogen atom, for R a hydrogen atom or a bromine atom, for R a or
- the reaction time is preferably about 10 minutes to about 1 hour.
- a pyrylium salt is precipitated as crystals.
- the thus formed precipitate is filtered out to obtain the end product pyrylium salt.
- Synthesis Example 2 In the same manner as described in Synthesis Example 1 using 2-hydroxy-a-naphthoaldehyde (ill-6) and 3-acetyl-9-ethylcarbazole (ll-3), a pyrylium salt having the following structural formula was synthesized;
- the absorption maximum wavelength of this compound in chloroform was 547 mu.
- Synthesis Example 3 In the same manner as described in Synthesis Example 1 using 2-hydroxy-5-nitrobenzaldehyde (Ill-5) and 3-acetyl-9-ethylcarbazole (ll-3 a pyrylium salt having the following structural formula was synthesized;
- the absorption maximum wavelength of this compound in chloroform was 574 mu.
- Synthesis Example 4 In the same manner as described in Synthesis Example 1 using 2-hydroxy-a-naphthoaldehyde (III-6) and 3-acetyl-6-bromo-9-ethylcarbazole (ll-8), a pyrylium salt having the following structural formula was synthesized;
- the absorption maximum wavelength of this compound in chloroform was 542 mu.
- this compound On infrared spectral analysis this compound showed a peak at 1665 cm, characteristic of the acetyl group, and the absorption maximum wavelength of the compound in chloroform was 596 mu. Thus, the compound was tinged blue.
- This compound also possesses a sensitizing effect on an organic photoconductive material, and is described in Japanese Patent Application No. 57400/72, (U.S Ser. N0-367,528,filed.lune,6,1973).
- carbazole nucleus-containing pyrylium salts show efficient sensitizing effects on various organic photoconductive materials.
- they are effective fororganic photoconductive materials of 2 the carbazole system such as those described in U.S.
- the sensitizer of the present invention is added to an organic photoconductive material in an amount of based on the weight of the'organic photoconductive material; t 1
- the organic photoconductive materials for "use in 'electro photography, sensitized with the sensitizer'of the present invention can be processed in eithera dry manner or a wet manner. Specific processing procedures thereof are described in U.S. Pat. Nos.
- an organic photoconductive material such 'as poly-N-vinylcarbazole and the pyrylium salts of the present invention are dissolved in an organic solvent such as a halogenated hydrocarbon, e.g., chloroform, methylene chloride, ethylene chloride, and coated on the conductive support so that the dried thickness is about 5 to 50 microns using bar coating.
- an organic solvent such as a halogenated hydrocarbon, e.g., chloroform, methylene chloride, ethylene chloride
- EXAMPLE 1 been subjected to electroconductivity-imparting processing (by coatingthereon Calgonite ConduetiyeP-olymer 261 (trade name'produced'by the Calgon- Corp.
- the thus obtained light-sensitive material wascharge'din the-dark,'imagewise exposed in an exposure amountof 1901-xlsec'using a white light-emitting source.
- a distinct image was reproduced.
- a developer comprising a carrier of nitrocellulose coated glass beads of a particle size of 0.4mm having adsorbed thereon a kneaded mixture of carbon black and polystyrene (5:5' by weight) was used.
- EXAMPLE 2 The pyrylium salt obtained in Synthesis Example 2 was added to 20 g of a poly-N-vinylcarbazole (as described in Example 1), and the sensitizing effect was examined in the same manner as described in Example 1. The results obtained are shown in the following Table 2.
- the thus obtained light-sensitive materials were charged in the dark, exposed to a white light-emitting source through an original image, and subjected to a development processing using a liquid developer prepared by dispersing l g of a commercially available black offset ink of the following composition in 1 liter of cyclohexane.
- alkali blue toner* rosin modified phenol-formaldehyde resin
- R represents R represents a hydrogen atom or a hydroxy group; or R and R when taken together form a substituted or unsubstituted benzene or naphthalene ring, said substituents being an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a nitro group or a halogen atom; R represents a hydrogen atom or R represents a hydrogen atom, a halogen atom, an amino group, an alkylamino group having from 1 to-4 carbon atoms or an alkyl group having 1 to 5 carbon atoms; X represents Cl, Br, I, ClOf, N0 H50 or BF ⁇ .
- the electrophotographic light-sensitive element of claim 1 wherein said sensitizer is 17 18 4.
- the eleetrophotographic light-sensitive element of claim 1 wherein said layer has a dried thickness of from 5 to 50 microns.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Indole Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47103809A JPS4963439A (enExample) | 1972-10-17 | 1972-10-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3909260A true US3909260A (en) | 1975-09-30 |
Family
ID=14363711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US406267A Expired - Lifetime US3909260A (en) | 1972-10-17 | 1973-10-15 | Sensitizer for use in electrophotographic light-sensitive material |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3909260A (enExample) |
| JP (1) | JPS4963439A (enExample) |
| DE (1) | DE2352112A1 (enExample) |
| GB (1) | GB1415950A (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4384034A (en) * | 1981-02-27 | 1983-05-17 | Minnesota Mining And Manufacturing Company | Thiopyrylium dye sensitized photoconductive materials |
| US4841050A (en) * | 1986-03-12 | 1989-06-20 | Basf Aktiengesellschaft | Carbazole containing benzopyrans |
| US20040038142A1 (en) * | 2000-02-21 | 2004-02-26 | Satoshi Yoshida | Developer, and image forming method and process cartridge using such developer |
| US20040101773A1 (en) * | 2002-11-27 | 2004-05-27 | Jiayi Zhu | Photoreceptor for electrophotography having a salt of an electron transport compound |
| US20040247933A1 (en) * | 2003-06-03 | 2004-12-09 | Canon Kabushiki Kaisha | Bipolar asymmetric carbazole-based host materials for electrophosphorescent guest-host OLED systems |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3240595A (en) * | 1959-02-26 | 1966-03-15 | Gevaert Photo Prod Nv | Electrophotographic material |
| US3240594A (en) * | 1959-02-26 | 1966-03-15 | Gevaert Photo Prod Nv | Electrophotographic material |
| US3655378A (en) * | 1971-03-01 | 1972-04-11 | Eastman Kodak Co | Charge-transfer complexes of dibenzofuran-formaldehyde or dibenzothiophene-formaldehyde resins as photoconductive materials |
-
1972
- 1972-10-17 JP JP47103809A patent/JPS4963439A/ja active Pending
-
1973
- 1973-10-15 US US406267A patent/US3909260A/en not_active Expired - Lifetime
- 1973-10-16 GB GB4822573A patent/GB1415950A/en not_active Expired
- 1973-10-17 DE DE19732352112 patent/DE2352112A1/de active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3240595A (en) * | 1959-02-26 | 1966-03-15 | Gevaert Photo Prod Nv | Electrophotographic material |
| US3240594A (en) * | 1959-02-26 | 1966-03-15 | Gevaert Photo Prod Nv | Electrophotographic material |
| US3655378A (en) * | 1971-03-01 | 1972-04-11 | Eastman Kodak Co | Charge-transfer complexes of dibenzofuran-formaldehyde or dibenzothiophene-formaldehyde resins as photoconductive materials |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4384034A (en) * | 1981-02-27 | 1983-05-17 | Minnesota Mining And Manufacturing Company | Thiopyrylium dye sensitized photoconductive materials |
| US4841050A (en) * | 1986-03-12 | 1989-06-20 | Basf Aktiengesellschaft | Carbazole containing benzopyrans |
| US20040038142A1 (en) * | 2000-02-21 | 2004-02-26 | Satoshi Yoshida | Developer, and image forming method and process cartridge using such developer |
| US20040101773A1 (en) * | 2002-11-27 | 2004-05-27 | Jiayi Zhu | Photoreceptor for electrophotography having a salt of an electron transport compound |
| EP1424601A3 (en) * | 2002-11-27 | 2005-01-19 | Samsung Electronics Co., Ltd. | Photoreceptor for electrophotography having a salt of an electron transport compound |
| US7045263B2 (en) | 2002-11-27 | 2006-05-16 | Samsung Electronics Co. Ltd. | Photoreceptor for electrophotography having a salt of an electron transport compound |
| CN100401195C (zh) * | 2002-11-27 | 2008-07-09 | 三星电子株式会社 | 具有电子传输化合物盐的电子照相用受光体 |
| US20040247933A1 (en) * | 2003-06-03 | 2004-12-09 | Canon Kabushiki Kaisha | Bipolar asymmetric carbazole-based host materials for electrophosphorescent guest-host OLED systems |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1415950A (en) | 1975-12-03 |
| DE2352112A1 (de) | 1974-04-18 |
| JPS4963439A (enExample) | 1974-06-19 |
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