JPH04360888A - New perylenetetracarboxylic acid diimide compound - Google Patents
New perylenetetracarboxylic acid diimide compoundInfo
- Publication number
- JPH04360888A JPH04360888A JP3163556A JP16355691A JPH04360888A JP H04360888 A JPH04360888 A JP H04360888A JP 3163556 A JP3163556 A JP 3163556A JP 16355691 A JP16355691 A JP 16355691A JP H04360888 A JPH04360888 A JP H04360888A
- Authority
- JP
- Japan
- Prior art keywords
- perylenetetracarboxylic acid
- acid diimide
- new
- bis
- compound
- 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.)
- Pending
Links
- -1 perylenetetracarboxylic acid diimide compound Chemical class 0.000 title description 9
- 229910000071 diazene Inorganic materials 0.000 title description 8
- 239000000126 substance Substances 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 6
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 5
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 abstract description 4
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 abstract description 4
- QMMOUZOFPLMXKW-UHFFFAOYSA-N 9,10-bis[[3-(trifluoromethyl)phenyl]carbamoyl]perylene-3,4-dicarboxylic acid Chemical compound C=12C3=C(C(=O)NC=4C=C(C=CC=4)C(F)(F)F)C=CC=1C(C1=4)=CC=C(C(O)=O)C=4C(C(=O)O)=CC=C1C2=CC=C3C(=O)NC1=CC=CC(C(F)(F)F)=C1 QMMOUZOFPLMXKW-UHFFFAOYSA-N 0.000 abstract description 2
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 238000010992 reflux Methods 0.000 abstract description 2
- 238000003756 stirring Methods 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000010410 layer Substances 0.000 description 5
- 239000013081 microcrystal Substances 0.000 description 5
- 108091008695 photoreceptors Proteins 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- PONZBUKBFVIXOD-UHFFFAOYSA-N 9,10-dicarbamoylperylene-3,4-dicarboxylic acid Chemical class C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=N)C2=C1C3=CC=C2C(=N)O PONZBUKBFVIXOD-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 2
- KJOLVZJFMDVPGB-UHFFFAOYSA-N perylenediimide Chemical compound C=12C3=CC=C(C(NC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)NC(=O)C4=CC=C3C1=C42 KJOLVZJFMDVPGB-UHFFFAOYSA-N 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 1
- SEMIDUTZXZKVAS-UHFFFAOYSA-N 4-(dibenzylamino)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 SEMIDUTZXZKVAS-UHFFFAOYSA-N 0.000 description 1
- RSRXYYMFVWHYBW-UHFFFAOYSA-N 9,10-bis(methylcarbamoyl)perylene-3,4-dicarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(=O)NC)C2=C1C3=CC=C2C(=O)NC RSRXYYMFVWHYBW-UHFFFAOYSA-N 0.000 description 1
- ALLZRPZUSMGILZ-UHFFFAOYSA-N 9,10-bis(phenylcarbamoyl)perylene-3,4-dicarboxylic acid Chemical compound C=12C3=C(C(=O)NC=4C=CC=CC=4)C=CC=1C(C1=4)=CC=C(C(O)=O)C=4C(C(=O)O)=CC=C1C2=CC=C3C(=O)NC1=CC=CC=C1 ALLZRPZUSMGILZ-UHFFFAOYSA-N 0.000 description 1
- QBNKJPMQSXPRNJ-UHFFFAOYSA-N 9,10-bis[(3,5-dimethylphenyl)carbamoyl]perylene-3,4-dicarboxylic acid Chemical compound CC1=CC(C)=CC(NC(=O)C=2C=3C(C(=O)NC=4C=C(C)C=C(C)C=4)=CC=C4C=5C=CC(=C6C(C(O)=O)=CC=C(C=56)C(C=34)=CC=2)C(O)=O)=C1 QBNKJPMQSXPRNJ-UHFFFAOYSA-N 0.000 description 1
- HGXPHWKUGASKLG-UHFFFAOYSA-N 9,10-bis[(4-chlorophenyl)carbamoyl]perylene-3,4-dicarboxylic acid Chemical compound C=12C3=C(C(=O)NC=4C=CC(Cl)=CC=4)C=CC=1C(C1=4)=CC=C(C(O)=O)C=4C(C(=O)O)=CC=C1C2=CC=C3C(=O)NC1=CC=C(Cl)C=C1 HGXPHWKUGASKLG-UHFFFAOYSA-N 0.000 description 1
- LRFWNVJMIOYNLP-UHFFFAOYSA-N 9,10-bis[(4-methoxyphenyl)carbamoyl]perylene-3,4-dicarboxylic acid Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC=C2C3=C1C(C(=O)NC=1C=CC(OC)=CC=1)=CC=C3C1=C3C2=CC=C(C(O)=O)C3=C(C(O)=O)C=C1 LRFWNVJMIOYNLP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical class [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- JGOAZQAXRONCCI-SDNWHVSQSA-N n-[(e)-benzylideneamino]aniline Chemical compound C=1C=CC=CC=1N\N=C\C1=CC=CC=C1 JGOAZQAXRONCCI-SDNWHVSQSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 229920001230 polyarylate Polymers 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
- 239000002244 precipitate Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Light Receiving Elements (AREA)
- Photoreceptors In Electrophotography (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は新規な３，４，９，１０
−ペリレンテトラカルボン酸ジイミド化合物に関する。
本発明に係わる化合物は、光電変換用材料として極めて
有用であり、太陽電池、光センサー、電子写真感光体等
に有効に利用できる。[Industrial Application Field] The present invention provides novel 3, 4, 9, 10
-Perylenetetracarboxylic acid diimide compound. The compound according to the present invention is extremely useful as a photoelectric conversion material, and can be effectively used in solar cells, optical sensors, electrophotographic photoreceptors, and the like.
【０００２】0002
【従来の技術】光電変換材料として数多くの物質が知ら
れている。中でも可視光域に感光性を示すものとして、
Ｓｉ、Ｓｅ、Ｓｅ／Ｔｅ、Ｓｅ／Ａｓ、ＣｄＳ等の無機
化合物がある。これら無機化合物の多くは、可撓性が無
く、従って加工性に難があり、大面積の光電変換素子が
作成困難であり、かつ毒性が強いものがある。その上、
高価に過ぎ、実用材料として多くの問題を抱えている。BACKGROUND OF THE INVENTION Many substances are known as photoelectric conversion materials. Among them, those that exhibit photosensitivity in the visible light range,
There are inorganic compounds such as Si, Se, Se/Te, Se/As, and CdS. Many of these inorganic compounds are not flexible and therefore have difficulty in processability, making it difficult to produce large-area photoelectric conversion elements, and some are highly toxic. On top of that,
It is too expensive and has many problems as a practical material.
【０００３】一方、有機化合物としては、メロシアニン
化合物、フタロシアニン化合物、ビスアゾ化合物、ペリ
レンテトラカルボン酸ジイミド化合物等の有機染・顔料
類が知られているが、光電変換効率において未だ改良の
余地がある。。On the other hand, as organic compounds, organic dyes and pigments such as merocyanine compounds, phthalocyanine compounds, bisazo compounds, and perylenetetracarboxylic acid diimide compounds are known, but there is still room for improvement in photoelectric conversion efficiency. .
【０００４】0004
【発明が解決しようとする課題】本発明の目的は、代表
的な有機光電変換材料の一つである３，４，９，１０−
ペリレンテトラカルボン酸ジイミド化合物類において、
光電変換効率が更に向上した誘導体を提供することであ
る。[Problems to be Solved by the Invention] The purpose of the present invention is to obtain 3,4,9,10-
In perylenetetracarboxylic acid diimide compounds,
The object of the present invention is to provide a derivative with further improved photoelectric conversion efficiency.
【０００５】[0005]
【課題を解決するための手段】本発明の課題は、化１の
式で表されるＮ，Ｎ´−ビス（２−、３−もしくは４−
トリフルオロメチルフェニル）−３，４，９，１０−ペ
リレンテトラカルボン酸ジイミドを、新規なペリレンテ
トラカルボン酸ジイミド化合物として採用することによ
って、その解決に進歩が見られた。[Means for Solving the Problem] An object of the present invention is to solve the problem of N,N'-bis(2-, 3- or 4-
Progress has been made in the solution by employing (trifluoromethylphenyl)-3,4,9,10-perylenetetracarboxylic acid diimide as a novel perylenetetracarboxylic acid diimide compound.
【０００６】公知の３，４，９，１０−ペリレンテトラ
カルボン酸ジイミド化合物としては、３，４，９，１０
−ペリレンテトラカルボン酸ジイミド、Ｎ，Ｎ´−ジメ
チル−３，４，９，１０−ペリレンテトラカルボン酸ジ
イミド、Ｎ，Ｎ´−ジフェニル−３，４，９，１０−ペ
リレンテトラカルボン酸ジイミド、Ｎ，Ｎ´−ビス（４
−メトキシフェニル）−３，４，９，１０−ペリレンテ
トラカルボン酸ジイミド、Ｎ，Ｎ´−ビス（４−クロロ
フェニル）−３，４，９，１０−ペリレンテトラカルボ
ン酸ジイミド、Ｎ，Ｎ´−ビス（３，５−ジメチルフェ
ニル）−３，４，９，１０−ペリレンテトラカルボン酸
ジイミド等があるが、いずれも光電変換効率において十
分とは言えない。尤も、これらの中では、Ｎ，Ｎ´−ビ
ス（３，５−ジメチルフェニル）−３，４，９，１０−
ペリレンテトラカルボン酸ジイミドが比較的高い光電変
換効率（電子写真感光体においては光感度）を与えるの
で実用レベルにある、との報告（高分子学会、印刷・情
報記録研究会予稿集、１９９１年２月２１〜２２日、東
京）が見られるが、本発明者の試験によれば一層の改善
が望まれることが判った。Known 3,4,9,10-perylenetetracarboxylic acid diimide compounds include 3,4,9,10-perylenetetracarboxylic acid diimide compounds.
-Perylenetetracarboxylic acid diimide, N,N'-dimethyl-3,4,9,10-perylenetetracarboxylic acid diimide, N,N'-diphenyl-3,4,9,10-perylenetetracarboxylic acid diimide, N ,N′-bis(4
-methoxyphenyl)-3,4,9,10-perylenetetracarboxylic acid diimide, N,N'-bis(4-chlorophenyl)-3,4,9,10-perylenetetracarboxylic acid diimide, N,N'- Although there are bis(3,5-dimethylphenyl)-3,4,9,10-perylenetetracarboxylic acid diimides, none of them can be said to have sufficient photoelectric conversion efficiency. Of course, among these, N,N'-bis(3,5-dimethylphenyl)-3,4,9,10-
A report states that perylenetetracarboxylic acid diimide provides relatively high photoelectric conversion efficiency (photosensitivity in electrophotographic photoreceptors) and is at a practical level (The Society of Polymer Science and Technology, Proceedings of the Printing and Information Recording Research Group, 1991, 2). However, according to the inventor's tests, it was found that further improvement is desired.
【０００７】本発明の化合物を合成するには、（１）２
−、３−もしくは４−トリフルオロメチルアニリンとナ
フタル酸（無水物）とからＮ−（２−、３−もしくは４
−トリフルオロメチルフェニル）−ナフタルイミドを得
て、それをＫＯＨで熔融する方法、あるいは（２）３，
４，９，１０−ペリレンテトラカルボン酸（二無水物）
へ２−、３−もしくは４−トリフルオロメチルアニリン
を反応させる方法、があるが、（２）の方法が最も容易
であった。To synthesize the compound of the present invention, (1)2
-, 3- or 4-trifluoromethylaniline and naphthalic acid (anhydride) to N-(2-, 3- or 4-trifluoromethylaniline and naphthalic acid (anhydride)
-trifluoromethylphenyl)-naphthalimide and melting it with KOH, or (2) 3,
4,9,10-perylenetetracarboxylic acid (dianhydride)
There are methods of reacting 2-, 3-, or 4-trifluoromethylaniline, but method (2) was the easiest.
【０００８】かくして合成された本発明の化合物は、有
機溶媒類に不溶で、熱時不融の、赤色系の微結晶であっ
た。そして、これらの微結晶は太陽電池、光センサー、
光スイッチング素子、電子写真感光体等の光電変換材料
として、公知の３，４，９，１０−ペリレンテトラカル
ボン酸ジイミド化合物に比して、高性能を発揮した。The compound of the present invention thus synthesized was in the form of red microcrystals that were insoluble in organic solvents and infusible when heated. These microcrystals are used in solar cells, optical sensors,
As a photoelectric conversion material for optical switching elements, electrophotographic photoreceptors, etc., it exhibited higher performance than known 3,4,9,10-perylenetetracarboxylic acid diimide compounds.
【０００９】[0009]
【実施例】次に、本発明を実施例により、さらに詳細に
説明する。なお、以下に示す部および％は、断りのない
限り重量基準である。EXAMPLES Next, the present invention will be explained in more detail with reference to examples. Note that parts and percentages shown below are based on weight unless otherwise specified.
【００１０】実施例１
Ｎ，Ｎ´−ビス（３−トリフルオロメチルフェニル）−
３，４，９，１０−ペリレンテトラカルボン酸ジイミド
の合成：３，４，９，１０−ペリレンテトラカルボン酸
二無水物２．５部へ３−トリフルオロメチルアニリン２
５部を加え、攪拌下に加熱・環流を５３時間続けた。放
冷後、エタノール１００容量部を加え、暫時加熱・攪拌
し、赤色沈殿を熱時瀘過・分離し、エタノールで洗い乾
燥した。この微結晶について、０．５％ＫＯＨ水溶液２
００容量部による熱時懸濁洗浄・瀘過を、瀘液が緑色蛍
光を示さなくなるまで計４回繰り返した後、水洗とメチ
ルエチルケトン洗浄とメタノール洗浄を行い、真空乾燥
した。ここに、赤色微結晶１．４０部（収率３２．４％
）を得た。Example 1 N,N'-bis(3-trifluoromethylphenyl)-
Synthesis of 3,4,9,10-perylenetetracarboxylic acid diimide: 3-trifluoromethylaniline 2 to 2.5 parts of 3,4,9,10-perylenetetracarboxylic dianhydride
5 parts were added, and heating and reflux were continued for 53 hours while stirring. After cooling, 100 parts by volume of ethanol was added, heated and stirred for a while, and the red precipitate was filtered and separated while hot, washed with ethanol and dried. Regarding this microcrystal, 0.5% KOH aqueous solution 2
The hot suspension washing and filtration using 00 parts by volume were repeated four times in total until the filtrate no longer exhibited green fluorescence, followed by washing with water, washing with methyl ethyl ketone, and washing with methanol, followed by vacuum drying. Here, 1.40 parts of red microcrystals (yield 32.4%)
) was obtained.
【００１１】かくして得た赤色微結晶について、元素分
析、赤外吸収スペクトル測定などを行った。
（１）元素分析：計算値 Ｃ ６７．２６％，Ｈ
２．３８％，Ｎ ４．１３％実測値 Ｃ ６７
．０９％，Ｈ ２．５６％，Ｎ ４．４７％
（２）赤外吸収スペクトル（ＫＢｒ錠剤）：図１The red microcrystals thus obtained were subjected to elemental analysis, infrared absorption spectrum measurement, etc. (1) Elemental analysis: Calculated value C 67.26%, H
2.38%, N 4.13% Actual value C 67
．． 09%, H 2.56%, N 4.47% (2) Infrared absorption spectrum (KBr tablet): Figure 1
【００
１２】実施例２
Ｎ，Ｎ´−ビス（３−トリフルオロメチルフェニル）−
３，４，９，１０−ペリレンテトラカルボン酸ジイミド
１部とポリエステル樹脂（東洋紡績製バイロン２００）
１部をテトラヒドロフラン１００部に混合し、ペイント
コンデイショナー装置により、ガラスビーズと共に２時
間分散した。こうして得た分散液をアプリケーターにて
、アルミ蒸着ポリエステルフィルム上に塗布して、膜厚
約０．２μｍの電荷発生層（光電変換作用により電荷を
発生する層）を形成した。塗布層は赤色を呈し、可視部
反射スペクトルにおける吸収極大波長は４７３．０ｎｍ
、５０１．０ｎｍ、５４８．０ｎｍおよび５７２．０ｎ
ｍ（肩）に認められた。次に、ｐ−ジベンジルアミノベ
ンズアルデヒド＝ジフェニルヒドラゾンを、ポリアリレ
ート樹脂（ユニチカ製Ｕ−ポリマー）と１：１の比で混
合し、ジクロロエタンを溶媒として１０％の溶液を作り
、上記の電荷発生層の上にアプリケーターにより塗布し
て、膜厚約２０μｍの電荷輸送層を形成した。00
12] Example 2 N,N'-bis(3-trifluoromethylphenyl)-
1 part of 3,4,9,10-perylenetetracarboxylic acid diimide and polyester resin (Vylon 200 manufactured by Toyobo Co., Ltd.)
One part was mixed with 100 parts of tetrahydrofuran and dispersed with glass beads for 2 hours using a paint conditioner device. The thus obtained dispersion was applied onto an aluminum-deposited polyester film using an applicator to form a charge generation layer (a layer that generates charges by photoelectric conversion) having a thickness of about 0.2 μm. The coating layer exhibits a red color, and the maximum absorption wavelength in the visible reflection spectrum is 473.0 nm.
, 501.0nm, 548.0nm and 572.0n
m (shoulder). Next, p-dibenzylaminobenzaldehyde=diphenylhydrazone was mixed with a polyarylate resin (U-polymer manufactured by Unitika) at a ratio of 1:1, a 10% solution was prepared using dichloroethane as a solvent, and the above charge generation layer was prepared. A charge transport layer having a thickness of about 20 μm was formed by applying the charge transport layer onto the film using an applicator.
【００１３】このようにして作成した積層型電子写真感
光体を、静電記録試験装置（川口電気製ＳＰ−４２８）
により電子写真特性評価試験を行った。
測定条件：印加電圧−６ｋＶ、スタテイックＮｏ．３（
ターンテーブルの回転スピードモード）その結果、電位
半減露光量は５．２８ルックス・秒なる値を示した。The laminated electrophotographic photoreceptor thus produced was tested using an electrostatic recording tester (SP-428 manufactured by Kawaguchi Electric).
An electrophotographic property evaluation test was conducted. Measurement conditions: Applied voltage -6kV, static No. 3(
Turntable rotation speed mode) As a result, the potential half-reduction exposure amount showed a value of 5.28 lux·sec.
【００１４】一方、本発明のＮ，Ｎ´−ビス（３−トリ
フルオロメチルフェニル）−３，４，９，１０−ペリレ
ンテトラカルボン酸ジイミドの代りに、比較用に同様の
方法で合成したＮ，Ｎ´−ビス（３，５−ジメチルフェ
ニル）−３，４，９，１０−ペリレンテトラカルボン酸
ジイミドを用いて、同様に作成した積層型電子写真感光
体について同じ試験を行ったところ、電位半減露光量は
２８．６０ルックス・秒なる値を示し，本発明の新規な
ペリレンテトラカルボン酸ジイミド化合物に比べて、遥
かに低活性であることが判明した。On the other hand, in place of the N,N'-bis(3-trifluoromethylphenyl)-3,4,9,10-perylenetetracarboxylic acid diimide of the present invention, for comparison, N , N'-bis(3,5-dimethylphenyl)-3,4,9,10-perylenetetracarboxylic acid diimide. When the same test was conducted on a laminated electrophotographic photoreceptor prepared in the same manner, the potential was The half-life exposure amount showed a value of 28.60 lux·sec, and it was found that the activity was much lower than that of the novel perylenetetracarboxylic acid diimide compound of the present invention.
【００１５】[0015]
【発明の効果】本発明を実施することにより、公知の３
，４，９，１０−ペリレンテトラカルボン酸ジイミド化
合物よりも光電変換作用が高活性の誘導体を得ることが
できた。Effect of the invention: By carrying out the present invention, three known
, 4,9,10-perylenetetracarboxylic acid diimide compound was able to obtain a derivative having a higher photoelectric conversion activity than that of the diimide compound.
【図１】本発明の化合物の一つであるＮ，Ｎ´−ビス（
３−トリフルオロメチルフェニル）−３，４，９，１０
−ペリレンテトラカルボン酸ジイミドの赤外吸収スペク
トル図（ＫＢｒ錠剤法）。[Figure 1] N,N'-bis(
3-trifluoromethylphenyl)-3,4,9,10
- Infrared absorption spectrum diagram of perylenetetracarboxylic acid diimide (KBr tablet method).
Claims (1)
−、３−もしくは４−トリフルオロメチルフェニル）−
３，４，９，１０−ペリレンテトラカルボン酸ジイミド
。 【化１】[Claim 1] N,N′-bis(2
-, 3- or 4-trifluoromethylphenyl)-
3,4,9,10-perylenetetracarboxylic acid diimide. [Chemical formula 1]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3163556A JPH04360888A (en) | 1991-06-06 | 1991-06-06 | New perylenetetracarboxylic acid diimide compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3163556A JPH04360888A (en) | 1991-06-06 | 1991-06-06 | New perylenetetracarboxylic acid diimide compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04360888A true JPH04360888A (en) | 1992-12-14 |
Family
ID=15776147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3163556A Pending JPH04360888A (en) | 1991-06-06 | 1991-06-06 | New perylenetetracarboxylic acid diimide compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04360888A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003101060A (en) * | 2001-09-20 | 2003-04-04 | National Institute Of Advanced Industrial & Technology | Organic photocurrent amplifier element and manufacturing method therefor |
-
1991
- 1991-06-06 JP JP3163556A patent/JPH04360888A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003101060A (en) * | 2001-09-20 | 2003-04-04 | National Institute Of Advanced Industrial & Technology | Organic photocurrent amplifier element and manufacturing method therefor |
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