JPH0414711B2 - - Google Patents
Info
- Publication number
- JPH0414711B2 JPH0414711B2 JP58201024A JP20102483A JPH0414711B2 JP H0414711 B2 JPH0414711 B2 JP H0414711B2 JP 58201024 A JP58201024 A JP 58201024A JP 20102483 A JP20102483 A JP 20102483A JP H0414711 B2 JPH0414711 B2 JP H0414711B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- unsubstituted
- lower alkyl
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000005504 styryl group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- -1 halogen ion Chemical class 0.000 claims description 10
- 150000002790 naphthalenes Chemical class 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical group [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
- 108091008695 photoreceptors Proteins 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- CNGYZEMWVAWWOB-VAWYXSNFSA-N 5-[[4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl]amino]-2-[(e)-2-[4-[[4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound N=1C(NC=2C=C(C(\C=C\C=3C(=CC(NC=4N=C(N=C(NC=5C=CC=CC=5)N=4)N(CCO)CCO)=CC=3)S(O)(=O)=O)=CC=2)S(O)(=O)=O)=NC(N(CCO)CCO)=NC=1NC1=CC=CC=C1 CNGYZEMWVAWWOB-VAWYXSNFSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- SVSCLSTYANOQQX-UHFFFAOYSA-N [diethoxyphosphoryl(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(P(=O)(OCC)OCC)C1=CC=CC=C1 SVSCLSTYANOQQX-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
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 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
Description
技術分野
本発明は新規なナフタレン誘導体及びその製造
法に関する。
従来技術
従来、電子写真方式において使用される感光体
の有機光導電性素材としてポリ−Ｎ−ビニルカル
バゾールをはじめ数多くの材料が提案されてい
る。
ここにいう「電子写真方式」とは一般に光導電
性の感光体を、まず暗所で例えばコロナ放電など
により帯電せしめ、ついで露光部のみの電荷を選
択的に放電させることにより静電潜像を得て、こ
の潜像部をトナーなどを用いた現像手段で可視化
して画像を形成するようにした画像形成法の一つ
である。このような電子写真方式における感光体
に要求される基本的な特性としては、(1)暗所にお
いて適当な電位に帯電されること、(2)暗所におけ
る電荷の放電が少ないこと、(3)光照射により速や
かに電荷を放電すること、などが挙げられる。し
かし、従来の光導電性有機材料はこれらの要求を
かならずしも満足していないのが実状である。
一方、セレンや酸化亜鉛は光導電性無機材料と
して知られており、中でもセレンは広く実用に供
されている。しかし、最近電子写真のプロセスの
点から、感光体に対する種々の要求、即わち一例
として前述の基本的特性に加えて、例えばその形
状についても可撓性のあるベルト状の感光体など
が要求されるようになつてきている。しかし、セ
レンの場合は一般にこのような形状のものに作成
することは困難である。
目 的
電子写真用の有機光導電性素材螢光増白剤とし
て使用することができ、特に電子写真用の上記要
望を満足する有機光導電性材料として有用なナフ
タレン誘導体及びその製造法を提供することであ
る。
構 成
第１の発明は、一般式（）
（式中Arは置換もしくは無置換のフエニル基、
または置換もしくは無置換のスチリル基、Ｒは水
素、低級アルキル基または、置換もしくは無置換
のフエニル基を表わす。Ｒが水素である場合Ar
は置換もしくは無置換のスチリル基である。）で
示されるナフタレン誘導体である。
第２の発明は、一般式（）
［式中Arは置換もしくは無置換フエニル基、ま
たは置換もしくは無置換のスチリル基、Ｒは水
素、低級アルキル基または置換もしくは無置換の
フエニル基を表わし、Ｒが水素である場合Arは
置換もしくは無置換のスチリル基である。Ｙは
TECHNICAL FIELD The present invention relates to a novel naphthalene derivative and a method for producing the same. Prior Art Conventionally, many materials including poly-N-vinylcarbazole have been proposed as organic photoconductive materials for photoreceptors used in electrophotography. The "electrophotographic method" referred to here generally means that a photoconductive photoreceptor is first charged in a dark place by, for example, corona discharge, and then the electrostatic latent image is formed by selectively discharging the charge only in the exposed areas. This is one of the image forming methods in which an image is formed by visualizing this latent image using a developing means using toner or the like. The basic characteristics required of a photoreceptor in such an electrophotographic method are (1) to be charged to an appropriate potential in a dark place, (2) to have little discharge of charge in a dark place, and (3) to be charged to an appropriate potential in a dark place. ) Promptly discharging charges by light irradiation. However, the reality is that conventional photoconductive organic materials do not necessarily satisfy these requirements. On the other hand, selenium and zinc oxide are known as photoconductive inorganic materials, and among them selenium is widely used in practical use. However, recently, in terms of the electrophotographic process, various demands have been placed on the photoreceptor. For example, in addition to the above-mentioned basic characteristics, there is also a demand for a flexible belt-like photoreceptor in terms of shape. This is becoming more and more common. However, in the case of selenium, it is generally difficult to create such a shape. Purpose: To provide a naphthalene derivative that can be used as an organic photoconductive material for electrophotography as a fluorescent brightener, and is particularly useful as an organic photoconductive material that satisfies the above requirements for electrophotography, and a method for producing the same. That's true. Configuration The first invention is based on the general formula () (In the formula, Ar is a substituted or unsubstituted phenyl group,
or a substituted or unsubstituted styryl group; R represents hydrogen, a lower alkyl group, or a substituted or unsubstituted phenyl group; When R is hydrogen, Ar
is a substituted or unsubstituted styryl group. ) is a naphthalene derivative represented by The second invention is the general formula () [In the formula, Ar represents a substituted or unsubstituted phenyl group, or a substituted or unsubstituted styryl group, R represents hydrogen, a lower alkyl group, or a substituted or unsubstituted phenyl group, and when R is hydrogen, Ar represents a substituted or unsubstituted styryl group. It is a substituted styryl group. Y is
【式】（ここでＺ
はハロゲン
イオンを示す）で表わされるトリフエニルホスホ
ニウム基、又は−PO（OR′）2（ここでR′は低級ア
ルキル基を示す）で表わされるジアルキル亜燐酸
基である］で表わされるフエニル誘導体と下記一
般式（）
で表わされるアルデヒド化合物とを反応させるこ
とを特徴とする下記一般式（）
（式中Arは置換もしくは無置換のフエニル基、
または置換もしくは無置換のスチリル基、Ｒは水
素、低級アルキル基、または置換もしくは無置換
のフエニル基を表わす。Ｒが水素である場合Ar
は置換もしくは無置換のスチリル基である。）で
表わされるナフタレン化合物の製造法である。
前記一般式（）ならびに（）中、Arまた
はＲにおける置換の場合の置換基あるいはArに
おけるスチリル基のベンゼン環上の置換基として
はメチル、エチル、プロピル、ブチルなどのアル
キル基、メトキシ、エトキシ、プロポキシ、ブト
キシなどのアルコキシ基、塩素、臭素などのハロ
ゲン原子などが挙げられる。
本発明で用いる一般式（）で表わされるフエ
ニル誘導体は対応するハロメチル化合物と亜リン
酸トリアルキル又はトフエニルホスフインとを直
接あるいはトルエン、テトラハイドロフラン、
Ｎ，Ｎ−ジメチルホルムアミドなどの溶媒中で加
熱することにより容易に製造される。ここで亜リ
ン酸トリアルキルとしては炭素数１〜４のアルキ
ル基、特にメチル基、エチル基が好ましい。
こうして得られた一般式（）で表わされるフ
エニル誘導体と一般式（）で表わされるアルデ
ヒド化合物とを塩基性触媒の存在下、室温から
100℃程度の温度において反応させる。
塩基性触媒としては苛性ソーダ、苛性カリ、ナ
トリウムアミド水素化ナトリウム及びナトリウム
メチラート、カリウム−ｔ−ブトキサイドなどの
アルコラートを挙げることができる。また、反応
溶媒としてはメタノール、エタノール、イソプロ
パノール、ブタノール、２−メトキシエタノー
ル、１，２−ジメトキシエタン、ビス（２−メト
キシエチル）エーテル、ジオキサン、テトラヒド
ロフラン、トルエン、キシレン、ジメチルスルホ
キシド、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ−メ
チルピロリドン、１，３−ジメチル−２−イミダ
ゾリジノンなどを挙げることができる。中でも極
性溶媒、例えばＮ，Ｎ−ジメチルホルムアミド、
及びジメチルスルホキシドが好適である。
反応温度は(1)使用する溶媒の塩基性触媒に対す
る安定性、(2)縮合成分（一般式（）及び（）
の化合物）の反応性、(3)前記塩基性触媒中におけ
る縮合剤としての反応性によつて広範囲に選択す
ることができる。例えば極性溶媒を用いるときは
実際には室温から100℃好ましくは室温から80℃
である。しかし反応時間の短縮又は活性の低い縮
合剤を使用するときはさらに高い温度でもよい。
このようにして得られる本発明にかかわる新規な
ナフタレン誘導体を例示すれば次の通りである。
実施例 １
１，１−ジフエニルメチルホスホン酸ジエチル
30.4ｇ（0.1モル）と４−Ｎ、Ｎ−ジフエニルア
ミノナフトアルデヒド32.3ｇ（0.1モル）をＮ，
Ｎ−ジメチルホルムアミド100mlに溶解し、これ
にカリウム−ｔ−ブトキサイド16.8ｇ（0.15モ
ル）を25〜30℃で加える。添加後８時間室温でか
きまぜを行なつた後、反応混合物を水200mlで希
釈した。析出した粉末を濾別、水洗、乾燥後、淡
黄色の粉末を得た。収量は38.9ｇ（収率82％）で
あつた。酢酸エチル−エタノールの混合溶媒から
再結晶した後、メタノールで洗浄し、１−Ｎ，Ｎ
−ジフエニルアミノ−４−（β−フエニルスチリ
ル）ナフタレンの純品を得た。熱分析の結果この
ものは200℃迄吸発熱のピークは観察されなかつ
た。A triphenylphosphonium group represented by [Formula] (where Z represents a halogen ion) or a dialkyl phosphorous group represented by -PO(OR') 2 (where R' represents a lower alkyl group) ] and the following general formula () The following general formula () is characterized by reacting with an aldehyde compound represented by (In the formula, Ar is a substituted or unsubstituted phenyl group,
or a substituted or unsubstituted styryl group; R represents hydrogen, a lower alkyl group, or a substituted or unsubstituted phenyl group; When R is hydrogen, Ar
is a substituted or unsubstituted styryl group. ) is a method for producing a naphthalene compound represented by In the general formulas () and (), the substituent in the case of substitution on Ar or R or the substituent on the benzene ring of the styryl group in Ar is an alkyl group such as methyl, ethyl, propyl, butyl, methoxy, ethoxy, Examples include alkoxy groups such as propoxy and butoxy, and halogen atoms such as chlorine and bromine. The phenyl derivative represented by the general formula () used in the present invention can be prepared by directly combining the corresponding halomethyl compound with trialkyl phosphite or tophenylphosphine, or by combining it with toluene, tetrahydrofuran,
It is easily produced by heating in a solvent such as N,N-dimethylformamide. Here, the trialkyl phosphite is preferably an alkyl group having 1 to 4 carbon atoms, particularly a methyl group or an ethyl group. The phenyl derivative represented by the general formula () obtained in this way and the aldehyde compound represented by the general formula () are mixed at room temperature in the presence of a basic catalyst.
The reaction is carried out at a temperature of approximately 100℃. As basic catalysts, mention may be made of caustic soda, caustic potash, sodium amide sodium hydride and alcoholates such as sodium methylate and potassium t-butoxide. In addition, reaction solvents include methanol, ethanol, isopropanol, butanol, 2-methoxyethanol, 1,2-dimethoxyethane, bis(2-methoxyethyl) ether, dioxane, tetrahydrofuran, toluene, xylene, dimethyl sulfoxide, N,N- Dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone and the like can be mentioned. Among them, polar solvents such as N,N-dimethylformamide,
and dimethyl sulfoxide are preferred. The reaction temperature depends on (1) the stability of the solvent used against basic catalysts, (2) the condensation components (general formulas () and ()
(3) Reactivity as a condensing agent in the basic catalyst can be selected from a wide range. For example, when using a polar solvent, the temperature should actually be between room temperature and 100°C, preferably between room temperature and 80°C.
It is. However, higher temperatures may be used if the reaction time is shortened or a less active condensing agent is used.
Examples of the novel naphthalene derivatives according to the present invention obtained in this way are as follows. Example 1 Diethyl 1,1-diphenylmethylphosphonate
30.4 g (0.1 mol) and 32.3 g (0.1 mol) of 4-N,N-diphenylaminonaphthaldehyde are
Dissolve in 100 ml of N-dimethylformamide and add 16.8 g (0.15 mol) of potassium t-butoxide at 25-30°C. After stirring at room temperature for 8 hours after the addition, the reaction mixture was diluted with 200 ml of water. The precipitated powder was separated by filtration, washed with water, and dried to obtain a pale yellow powder. The yield was 38.9 g (yield 82%). After recrystallizing from a mixed solvent of ethyl acetate and ethanol, washing with methanol, 1-N,N
A pure product of -diphenylamino-4-(β-phenylstyryl)naphthalene was obtained. As a result of thermal analysis, no endothermic peak was observed up to 200°C.
【表】
赤外線吸収スペクトル（KBr錠剤法）を図１
に示した。
実施例 ２〜５
実施例１と同様にして得られたナフタレン誘導
体について表１に示す。[Table] Infrared absorption spectrum (KBr tablet method) is shown in Figure 1.
It was shown to. Examples 2 to 5 Table 1 shows naphthalene derivatives obtained in the same manner as in Example 1.
【表】【table】
【表】
効 果
以上の説明から明らかなように本発明に係るナ
フタレン誘導体は新規な化合物であつて、特に電
子写真用有機光導電性材料として有効なものであ
る。[Table] Effects As is clear from the above description, the naphthalene derivative according to the present invention is a new compound, and is particularly effective as an organic photoconductive material for electrophotography.
図１は１−Ｎ，Ｎ−ジフエニルアミノ−４−
（β−フエニルスチリル）ナフタレンの赤外線吸
収スペクトル図である。
Figure 1 shows 1-N,N-diphenylamino-4-
It is an infrared absorption spectrum diagram of (β-phenylstyryl) naphthalene.
Claims (1)
または置換もしくは無置換のスチリル基、Ｒは水
素、低級アルキル基または、置換もしくは無置換
のフエニル基を表わす。Ｒが水素である場合、
Arは置換もしくは無置換のスチリル基である。
以上において、置換の場合の置換基は、低級アル
キル基、低級アルコキシ基、ハロゲン原子を表わ
す。）で示されるナフタレン誘導体。 ２ 一般式（） ［式中Arは置換もしくは無置換フエニル基、ま
たは置換もしくは無置換スチリル基、Ｒは水素、
低級アルキル基または置換もしくは無置換フエニ
ル基を表わし、Ｒが水素である場合、Arは置換
もしくは無置換のスチリル基である。以上におい
て、置換の場合の置換基は、低級アルキル基、低
級アルコキシ基、ハロゲン原子を表わす。Ｙは
【式】（ここでＺ はハロゲン イオンを示す）で表わされるトリフエニルホスホ
ニウム基、又は−PO（OR′）2（ここでR′は低級ア
ルキル基を示す）で表わされるジアルキル亜燐酸
基である］で表わされるフエニル誘導体と下記一
般式（） で表わされるアルデヒド化合物とを反応させるこ
とを特徴とする下記一般式（） （式中Arは置換もしくは無置換のフエニル基、
または置換もしくは無置換のスチリル基、Ｒは水
素、低級アルキル基、または置換もしくは無置換
のフエニル基を表わす。Ｒが水素である場合、
Arは置換もしくは無置換のスチリル基である。
以上において、置換の場合の置換基は、低級アル
キル基、低級アルコキシ基、ハロゲン原子を表わ
す。）で表わされるナフタレン誘導体の製造法。[Claims] 1 General formula () (In the formula, Ar is a substituted or unsubstituted phenyl group,
or a substituted or unsubstituted styryl group; R represents hydrogen, a lower alkyl group, or a substituted or unsubstituted phenyl group; When R is hydrogen,
Ar is a substituted or unsubstituted styryl group.
In the above, the substituent in the case of substitution represents a lower alkyl group, a lower alkoxy group, or a halogen atom. ) naphthalene derivatives. 2 General formula () [In the formula, Ar is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted styryl group, R is hydrogen,
It represents a lower alkyl group or a substituted or unsubstituted phenyl group, and when R is hydrogen, Ar is a substituted or unsubstituted styryl group. In the above, the substituent in the case of substitution represents a lower alkyl group, a lower alkoxy group, or a halogen atom. Y is a triphenylphosphonium group represented by the formula (where Z represents a halogen ion) or a dialkyl phosphorous group represented by -PO(OR') 2 (where R' represents a lower alkyl group) phenyl derivatives represented by ] and the following general formula () The following general formula () is characterized by reacting with an aldehyde compound represented by (In the formula, Ar is a substituted or unsubstituted phenyl group,
or a substituted or unsubstituted styryl group; R represents hydrogen, a lower alkyl group, or a substituted or unsubstituted phenyl group; When R is hydrogen,
Ar is a substituted or unsubstituted styryl group.
In the above, the substituent in the case of substitution represents a lower alkyl group, a lower alkoxy group, or a halogen atom. ) A method for producing a naphthalene derivative represented by
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58201024A JPS6094461A (en) | 1983-10-28 | 1983-10-28 | Naphthaelene derivative and production thereof |
| US06/646,064 US4603097A (en) | 1983-10-28 | 1984-08-31 | Styrene derivatives and electrophotographic photoconductor comprising one of the styrene derivatives |
| DE19843439113 DE3439113A1 (en) | 1983-10-28 | 1984-10-25 | STYRENE DERIVATIVES AND ELECTROPHOTOGRAPHIC PHOTO LADDERS, WHICH CONTAIN AT LEAST ONE OF THE DERIVATIVES |
| GB08427280A GB2151223B (en) | 1983-10-28 | 1984-10-29 | Styrene derivatives and electrophotograhic photoconductors containing them |
| US07/545,124 US5072043A (en) | 1983-10-28 | 1990-06-27 | Styrene derivatives and electrophotographic photoconductor comprising one of the styrene derivatives |
| US07/754,552 US5292896A (en) | 1983-10-28 | 1991-09-04 | Amino styrene derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58201024A JPS6094461A (en) | 1983-10-28 | 1983-10-28 | Naphthaelene derivative and production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6094461A JPS6094461A (en) | 1985-05-27 |
| JPH0414711B2 true JPH0414711B2 (en) | 1992-03-13 |
Family
ID=16434187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58201024A Granted JPS6094461A (en) | 1983-10-28 | 1983-10-28 | Naphthaelene derivative and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6094461A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02277070A (en) * | 1989-04-19 | 1990-11-13 | Somar Corp | Organic photosensitive body containing substituted naphthalene compound |
-
1983
- 1983-10-28 JP JP58201024A patent/JPS6094461A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6094461A (en) | 1985-05-27 |
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