JPH0657689B2 - Fluorene derivative - Google Patents
Fluorene derivativeInfo
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- JPH0657689B2 JPH0657689B2 JP1087860A JP8786089A JPH0657689B2 JP H0657689 B2 JPH0657689 B2 JP H0657689B2 JP 1087860 A JP1087860 A JP 1087860A JP 8786089 A JP8786089 A JP 8786089A JP H0657689 B2 JPH0657689 B2 JP H0657689B2
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- fluorene
- melting point
- compound represented
- structural formula
- fluorene derivative
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Description
【発明の詳細な説明】 産業上の利用分野 本発明は、電子写真感光材料として有用な新規なフルオ
レン誘導体に関する。TECHNICAL FIELD The present invention relates to a novel fluorene derivative useful as an electrophotographic photosensitive material.
従来の技術 従来、有機光導電材料を用いた電子写真感光体について
は、可視光を吸収して電荷を発生する電荷発生材を含む
電荷発生層と、その電荷の輸送を行う電荷輸送材を含む
電荷輸送層とに機能分離された層構成を有する積層型の
感光層を作成することが行われている。そして、電荷輸
送材としては、アミン系化合物、ヒドラゾン化合物、ピ
ラゾリン化合物、オキサジアゾール化合物、スチルベン
化合物、カルバゾール化合物等、正孔輸送性の種々のも
のが知られている。2. Description of the Related Art Conventionally, an electrophotographic photosensitive member using an organic photoconductive material includes a charge generation layer including a charge generation material that absorbs visible light and generates an electric charge, and a charge transport material that transfers the electric charge. A laminated type photosensitive layer having a layer structure in which the function is separated into a charge transport layer is prepared. As the charge transport material, various materials having a hole transport property such as amine compounds, hydrazone compounds, pyrazoline compounds, oxadiazole compounds, stilbene compounds and carbazole compounds are known.
発明が解決しようとする課題 ところで、機能分離型の電子写真感光体においては、機
械的強度の強い電荷輸送層を上層とすることが一般的
で、従来の正孔輸送材料を用いた場合、負帯電型とな
る。しかしながら、コロトロンにおけるオゾンの発生防
止、現像剤におけるトナーの帯電制御等の点から、正帯
電型の方が望ましい。電子写真感光体を正帯電型として
用いる場合、電荷輸送層を上層として用いるには電子輸
送材が必要であるが、従来充分有効な電子輸送材は知ら
れていない。DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention By the way, in a function-separated type electrophotographic photoreceptor, it is common to use a charge transport layer having high mechanical strength as an upper layer. It becomes a charge type. However, the positive charging type is preferable from the viewpoints of preventing the generation of ozone in the corotron and controlling the charging of the toner in the developer. When the electrophotographic photoreceptor is used as a positive charging type, an electron transport material is required to use the charge transport layer as an upper layer, but a sufficiently effective electron transport material has not been known so far.
本発明は、この様な事情に鑑みてなされたもので、正帯
電用の積層型電子写真感光体における電子輸送材として
有用な有機光導電性材料を提供することを目的とする。The present invention has been made in view of such circumstances, and an object of the present invention is to provide an organic photoconductive material useful as an electron transport material in a laminate type electrophotographic photoreceptor for positive charging.
本発明者等は、種々の化合物を合成し、その電子写真特
性について検討した結果、ある一群のフルオレン誘導体
が、電子輸送材として優れたものであることを見出だ
し、本発明を完成するに至った。As a result of synthesizing various compounds and examining their electrophotographic properties, the present inventors have found that a certain group of fluorene derivatives are excellent as electron transport materials, and have completed the present invention. It was
課題を解決するための手段 本発明のフルオレン誘導体は、下記一般式（Ｉ）で示さ
れる。Means for Solving the Problems The fluorene derivative of the present invention is represented by the following general formula (I).
（式中、Ｒ１は水素原子又はフェニル基を表わし、Ｒ２
は水素原子、ニトロ基又はアルコキシカルボニル基を表
わし、Ｒ３及びＲ４は、それぞれ水素原子又はアルキル
基を表わす） 上記一般式（Ｉ）で示されるフルオレン誘導体におい
て、好ましいものは基 がフルオレン核の２位又は４位に存在するものである。
又、Ｒ２がアルコキシカルボニル基を示す場合には、炭
素数２〜９個の基であることが好ましい。 (In the formula, R 1 represents a hydrogen atom or a phenyl group, and R 2
Represents a hydrogen atom, a nitro group or an alkoxycarbonyl group, and R 3 and R 4 each represent a hydrogen atom or an alkyl group.) In the fluorene derivative represented by the general formula (I), a preferable group is Is present at the 2 or 4 position of the fluorene nucleus.
When R 2 represents an alkoxycarbonyl group, it is preferably a group having 2 to 9 carbon atoms.
本発明の上記フルオレン誘導体は、下記反応式で示すよ
うに、一般式（II）で示されるフルオレン誘導体をピリ
ジン等の溶剤中で酸化して、一般式（III）で示される
フルオレノン誘導体を合成し、次いで、ピリジン等の溶
剤中でマロンニトリルと加熱還流することによって製造
することができる。The fluorene derivative of the present invention is obtained by oxidizing a fluorene derivative represented by the general formula (II) in a solvent such as pyridine to synthesize a fluorenone derivative represented by the general formula (III), as shown in the following reaction formula. Then, it can be produced by heating under reflux with malonnitrile in a solvent such as pyridine.
（式中、Ｒ１ないしＲ４は上記の定義と同一である） なお、一般式（II）で示されるフルオレン誘導体は、ホ
ルミルフルオレンを、例えばジエチルジフェニルメチル
ホスホナートと反応させるか、或いは、クロロメチルフ
ルオレンをトリフェニルホスフィンと反応させ、次い
で、相当するベンズアルデヒドと縮合して合成すること
ができる。 (In the formula, R 1 to R 4 are the same as the above definition.) The fluorene derivative represented by the general formula (II) is obtained by reacting formylfluorene with, for example, diethyldiphenylmethylphosphonate, or chloro. It can be synthesized by reacting methylfluorene with triphenylphosphine and then condensing with the corresponding benzaldehyde.
本発明の上記一般式（Ｉ）で示されるフルオレン誘導体
は、優れた電子輸送性を示し、電子写真感光体の電子輸
送材として使用した場合、優れた電子写真特性を示す正
帯電用電子写真感光体を製造することができる。The fluorene derivative represented by the above general formula (I) of the present invention exhibits excellent electron transporting properties and, when used as an electron transporting material of an electrophotographic photosensitive member, exhibits excellent electrophotographic characteristics. The body can be manufactured.
実施例 実施例１ 2-ホルミルフルオレンとジエチルジフェニルメチルホス
ホナートとをｎ−ブチルリチウムの存在下、テトラヒド
ロフラン中で還流して反応させることによって得られた
下記構造式 で示されるフルオレン化合物（m.p.136.5〜138℃）6.5
ｇ及びピリジン100ｍを、150ｍの三つ口フラスコに
入れ、氷冷し、ベンジルトリメチルアンモニウム・ヒド
ロキシドの40％メタノール溶液0.5ｍを加え、酸素気
流中で１時間撹拌した。反応終了後、内容物を水100ｍ
中に注入し、生成した黄色沈澱を濾別し、希塩酸、次
いで水で洗浄した。次いで、塩化メチレンに溶解し、Na
2SO4で乾燥した後、シリカゲルショートカラム（塩化メ
チレン／ヘキサン＝１／１）で精製し、溶媒を減圧留去
した後、残渣を酢酸エチル−エタノール混液から再結晶
して、下記構造式 で示されるフルオレノン化合物6.5ｇ（収率94％）を橙
黄色針状結晶として得た。融点：172〜173.5℃。Examples Example 1 The following structural formula obtained by refluxing 2-formylfluorene and diethyldiphenylmethylphosphonate in tetrahydrofuran in the presence of n-butyllithium for reaction Fluorene compound represented by (mp136.5-138 ℃) 6.5
g and 100 m of pyridine were placed in a 150 m three-necked flask, cooled with ice, 0.5 m of a 40% methanol solution of benzyltrimethylammonium hydroxide was added, and the mixture was stirred in an oxygen stream for 1 hour. After the reaction is completed, the content is 100m of water
It was poured into and the yellow precipitate formed was filtered off and washed with dilute hydrochloric acid and then with water. Then dissolve in methylene chloride and add Na
After drying with 2 SO 4 , it was purified with a silica gel short column (methylene chloride / hexane = 1/1), the solvent was distilled off under reduced pressure, and the residue was recrystallized from a mixed solution of ethyl acetate-ethanol. 6.5 g (yield 94%) of a fluorenone compound represented by are obtained as orange-yellow needle crystals. Melting point: 172-13.5 ° C.
このフルオレノン誘導体5.0ｇをピリジン90ｍと共に2
50ｍ三つ口フラスコに入れ、窒素気流中100℃に加熱
して溶解した後、マロンニトリル1.8ｇをピリジン10ｍ
に溶解した溶液を、約10分間で滴下し、滴下終了後、
混合物を１時間還流した。次いで室温まで冷却した後、
反応混合物を水100ｍ中に注入し、生成した沈澱を濾
別し、ピリジン、希塩酸、水、メタノールの順に洗浄し
て、下記構造式 で示されるフルオレン化合物（化合物１）5.5ｇ（収率9
7％）を茶褐色粉末として得た。融点：293〜295.5℃ 元素分析： 質量分析：Ｍ＋406 ＵＶ吸収スペクトルλmax：525nm、323nm CH2Cl2中 赤外吸収スペクトル：2220cm-1(KBr) 実施例２ 2,7-ジ-t-ブチル-4-クロルメチルフルオレンをトリフェ
ニルホスフィンと反応させ、次いで、4-ニトロベンズア
ルデヒドと縮合して得られた下記構造式 で示されるフルオレン化合物（融点205.5〜207.5℃）5.
0ｇを、水酸化カリウム0.3ｇ及びピリジン100ｍと共
に、200ｍの丸底フラスコに入れ、空気雰囲気下で室
温において20時間撹拌した。反応終了後、200ｍの水
を加え、塩化メチレンで抽出した後、有機層をＮａ２Ｓ
Ｏ４で乾燥した。溶媒を減圧留去した後、残渣をシリカ
ゲルショートカラム（塩化メチレン／ヘキサン＝2/1）
で精製した。溶媒を減圧留去した後、残渣を酢酸エチル
−エタノール混液から再結晶して、下記構造式 で示されるフルオレノン化合物1.7ｇ（収率33％）を黄
色粉末として得た。融点：223〜224℃。5.0g of this fluorenone derivative together with 90m of pyridine
Put in a 50m three-necked flask, heat to 100 ° C in a nitrogen stream to dissolve, and then dissolve 1.8g of malonnitrile in 10m of pyridine
The solution dissolved in was dripped in about 10 minutes, after the dropping,
The mixture was refluxed for 1 hour. Then after cooling to room temperature,
The reaction mixture was poured into 100 m of water, the precipitate formed was filtered off, washed with pyridine, dilute hydrochloric acid, water and methanol in this order, and 5.5 g of fluorene compound (compound 1) represented by
7%) as a brown powder. Melting point: 293-295.5 ° C Elemental analysis: Mass spectrum: M + 406 UV absorption spectrum λmax: 525 nm, 323 nm In CH 2 Cl 2 Infrared absorption spectrum: 2220 cm −1 (KBr) Example 2 2,7-di-t-butyl-4-chloromethylfluorene The following structural formula obtained by reacting with phenylphosphine and then condensing with 4-nitrobenzaldehyde Fluorene compound represented by (melting point 205.5 to 207.5 ° C) 5.
0 g was placed in a 200 m round bottom flask with 0.3 g potassium hydroxide and 100 m pyridine and stirred for 20 hours at room temperature under air atmosphere. After the reaction was completed, 200 m of water was added and extracted with methylene chloride, and then the organic layer was added to Na 2 S.
Dry with O 4 . After distilling off the solvent under reduced pressure, the residue was put on a silica gel short column (methylene chloride / hexane = 2/1).
Purified in. After distilling off the solvent under reduced pressure, the residue was recrystallized from a mixed solution of ethyl acetate-ethanol to give the following structural formula. 1.7 g (yield 33%) of a fluorenone compound represented by was obtained as a yellow powder. Melting point: 223-224 ° C.
このフルオレノン誘導体110mg、マロンニトリル0.33
ｇ、及びピリジン50ｍを、100ｍ枝付きフラスコに
入れ、混合物を窒素気流中１時間還流した後、ピリジン
を減圧留去した。残渣を塩化メチレンに溶かし、シリカ
ゲルショートカラム（塩化メチレンで溶出）で精製し
た。塩化メチレンを減圧留去した後、残渣をメタノール
で洗浄し、酢酸エチルから再結晶して、下記構造式 で示されるフルオレノン化合物（化合物２）0.84ｇ（収
率69％）を赤茶色針状結晶として得た。融点：289〜290
℃。This fluorenone derivative 110 mg, malonnitrile 0.33
g and 50 m of pyridine were placed in a 100 m branched flask, and the mixture was refluxed in a nitrogen stream for 1 hour, and then pyridine was distilled off under reduced pressure. The residue was dissolved in methylene chloride and purified by silica gel short column (eluted with methylene chloride). After distilling off methylene chloride under reduced pressure, the residue was washed with methanol and recrystallized from ethyl acetate to obtain the following structural formula. 0.84 g (yield 69%) of a fluorenone compound represented by (Compound 2) was obtained as reddish brown needle crystals. Melting point: 289-290
° C.
元素分析： 質量分析：Ｍ＋487 ＵＶ吸収スペクトルλmax：366nm、259nm CH2Cl2中 赤外吸収スペクトル：2224、1594、1528、1344cm-1(KBr) 実施例３ 4-クロルメチルフルオレンをトリフェニルホスフィンと
反応させ、次いで、4-ホルミル安息香酸ブチルを反応さ
せることによって合成された下記構造式 で示されるフルオレン化合物（融点76〜77℃）を、実施
例２におけると同様にして処理して、シリカゲルカラム
（塩化メチレン／ヘキサン＝1/2〜1/0）で精製し、下記
構造式 で示されるフルオレノン化合物［シス体、融点：96.5〜
97.5℃（収率7.7％）、トランス体、融点：116〜117.5
℃（収率81.3％）］を得た。Elemental analysis: Mass spectrum: M + 487 UV absorption spectrum λmax: 366 nm, 259 nm In CH 2 Cl 2 Infrared absorption spectrum: 2224, 1594, 1528, 1344 cm −1 (KBr) Example 3 4-Chloromethylfluorene was reacted with triphenylphosphine, Then, the following structural formula synthesized by reacting butyl 4-formylbenzoate The fluorene compound represented by the formula (melting point: 76 to 77 ° C.) was treated in the same manner as in Example 2 and purified by a silica gel column (methylene chloride / hexane = 1/2 to 1/0). Fluorenone compound represented by [cis isomer, melting point: 96.5-
97.5 ° C (7.7% yield), trans form, melting point: 116-117.5
C (yield 81.3%)] was obtained.
上記のトランス体を用い、実施例２におけると同様に処
理して、下記構造式 で示されるフルオレン化合物（化合物３）を赤橙色針状
結晶として得た。融点：171〜172℃（収率77.6％） 元素分析： 質量分析：Ｍ＋430 ＵＶ吸収スペクトルλmax：345nm、316nm、267nm 赤外吸収スペクトル：2220、1730、1708cm-1(KBr)、2224、1
712cm-1(CHCl3) 実施例４ 実施例３において得られた構造式（１）で示されるフル
オレノン化合物のシス体を用い、実施例２におけると同
様に処理して、下記構造式 で示されるフルオレン化合物（化合物４）を橙色粉末と
して得た。融点：163〜165℃（収率81.2％） 元素分析： 質量分析：Ｍ＋430 ＵＶ吸収スペクトルλmax：358nm、297nm、286nm、270nm 赤外吸収スペクトル：2224、1718cm-1(KBr) 実施例５ 下記構造式 （式中、Ｐｈはフェニル基を表わす） で示されるフルオレン化合物と4-ホルミル安息香酸オク
チルを反応させることによって合成された下記構造式 で示されるフルオレン化合物（融点：67〜73℃）を、実
施例２におけると同様にして処理して、シリカゲルカラ
ム（塩化メチレン／ヘキサン＝1/2〜1/0）で精製し、下
記構造式 で示されるフルオレノン化合物［シス体、融点：81〜83
℃（収率6.9％）、トランス体、融点：113.5〜114.5℃
（収率80.2％）］を得た。Using the above trans form, the same treatment as in Example 2 was carried out, and the following structural formula The fluorene compound represented by (Compound 3) was obtained as reddish orange needle crystals. Melting point: 171-172 ° C (77.6% yield) Elemental analysis: Mass spectrum: M + 430 UV absorption spectrum λmax: 345nm, 316nm, 267nm Infrared absorption spectrum: 2220, 1730, 1708cm -1 (KBr), 2224, 1
712 cm -1 (CHCl 3 ) Example 4 Using the cis form of the fluorenone compound represented by the structural formula (1) obtained in Example 3, the same treatment as in Example 2 was carried out, and the following structural formula The fluorene compound represented by (Compound 4) was obtained as an orange powder. Melting point: 163-165 ° C (yield 81.2%) Elemental analysis: Mass spectrum: M + 430 UV absorption spectrum λmax: 358 nm, 297 nm, 286 nm, 270 nm Infrared absorption spectrum: 2224, 1718 cm -1 (KBr) Example 5 Structural formula below (Wherein Ph represents a phenyl group) and the following structural formula synthesized by reacting octyl 4-formylbenzoate with The fluorene compound represented by (melting point: 67 to 73 ° C.) was treated in the same manner as in Example 2 and purified by a silica gel column (methylene chloride / hexane = 1/2 to 1/0). Fluorenone compound represented by [cis isomer, melting point: 81-83
℃ (yield 6.9%), trans form, melting point: 113.5-114.5 ℃
(Yield 80.2%)] was obtained.
上記のトランス体を用い、実施例２におけると同様に処
理して、下記構造式 で示されるフルオレン化合物（化合物５）を赤橙色針状
結晶として得た。融点142〜144℃（収率82.0％） 元素分析 質量分析：Ｍ＋486 ＵＶ吸収スペクトルλmax：345nm、315nm、265nm 赤外吸収スペクトル：2220、1728、1710cm-1(KBr) 実施例６ 実施例５において得られた構造式（２）で示されるフル
オレノン化合物のシス体を用い、実施例２におけると同
様に処理して、下記構造式 で示されるフルオレン化合物（化合物６）を橙色綿状結
晶として得た。融点：120〜121.5℃（収率60.4％） 元素分析： 質量分析：Ｍ＋486 ＵＶ吸収スペクトルλmax：355nm、297nm、285nm、270nm 赤外吸収スペクトル：2224、1708cm-1(KBr) 応用例１ 導電性基板上に、三方晶系セレン／ポリビニルカルバゾ
ール（三方晶系セレン：７容量％）からなる電荷発生層
（2.5μｍ）を設け、その上に、化合物３、４、５又は
６ 0.5ｇ及びポリカーボネート0.75ｇを塩化メチレン
７ｇに溶解した溶液を、湿潤時のギャップ５ミルで塗布
し乾燥して、電子写真感光体を作成した。これらの電子
写真感光体について、静電複写紙試験装置（SP428、川
口電機製作所（株）製）を用いて＋800V及び−800Vに帯
電し、５ルックスの白色光を露光し、感度(dV/dT)を測
定した。結果を第１表に示す。Using the above trans form, the same treatment as in Example 2 was carried out, and the following structural formula A fluorene compound represented by (Compound 5) was obtained as reddish orange needle crystals. Melting point 142-144 ℃ (Yield 82.0%) Elemental analysis Mass spectrum: M + 486 UV absorption spectrum λmax: 345 nm, 315 nm, 265 nm Infrared absorption spectrum: 2220, 1728, 1710 cm −1 (KBr) Example 6 Example 6 of the fluorenone compound represented by the structural formula (2) obtained in Example 5 Using the cis form, the same treatment as in Example 2 was carried out, and the following structural formula A fluorene compound represented by (Compound 6) was obtained as orange cotton crystals. Melting point: 120-121.5 ° C (yield 60.4%) Elemental analysis: Mass spectrum: M + 486 UV absorption spectrum λmax: 355nm, 297nm, 285nm, 270nm Infrared absorption spectrum: 2224, 1708cm -1 (KBr) Application example 1 Trigonal selenium / polyvinylcarbazole (trigonal selenium) on a conductive substrate. : 7% by volume), a charge generation layer (2.5 μm) is provided, on which a solution of 0.5 g of compound 3, 4, 5 or 6 and 0.75 g of polycarbonate dissolved in 7 g of methylene chloride is added, and a gap 5 when wet is formed. It was coated with a mill and dried to prepare an electrophotographic photoreceptor. These electrophotographic photoconductors were charged to +800 V and −800 V by using an electrostatic copying paper tester (SP428, manufactured by Kawaguchi Denki Seisakusho Co., Ltd.), exposed to white light of 5 lux, and sensitivity (dV / dT ) Was measured. The results are shown in Table 1.
参考例 化合物３の代わりに2,4,7-トリニトロフルオレノン(TN
F)を用いた以外は、応用例１におけると同様にして電子
写真感光体を作成し、同様にして感度を測定した。結果
を第１表に示す。Reference example 2,4,7-trinitrofluorenone (TN
An electrophotographic photosensitive member was prepared in the same manner as in Application Example 1 except that F) was used, and the sensitivity was measured in the same manner. The results are shown in Table 1.
応用例２ 導電性基板上に、無金属フタロシアニンを蒸着して、厚
さ0.1μｍの電荷発生層を形成した。一方、化合物１ま
たは２ 0.5ｇ及びビスフェノールＡポリカーボネート
0.75ｇを1,2ジクロルエタンに分散させ、ボールミルで
処理した後、得られた分散物を、上記電荷発生層上に、
湿潤時のギャップ７ミルで塗布し乾燥して、電子写真感
光体を作成した。これらの電子写真感光体について、応
用例１におけると同様にして感度を測定した。ただし、
表面電位＋500V及び−500Vに帯電した。結果を第１表に
示す。Application Example 2 Metal-free phthalocyanine was vapor-deposited on a conductive substrate to form a charge generation layer having a thickness of 0.1 μm. On the other hand, compound 1 or 2 0.5 g and bisphenol A polycarbonate
After 0.75 g was dispersed in 1,2 dichloroethane and treated with a ball mill, the resulting dispersion was placed on the above charge generation layer.
A wet gap of 7 mil was applied and dried to prepare an electrophotographic photoreceptor. The sensitivity of these electrophotographic photosensitive members was measured in the same manner as in Application Example 1. However,
The surface potential was charged to + 500V and -500V. The results are shown in Table 1.
発明の効果 本発明の上記一般式（Ｉ）で示されるフルオレン誘導体
は、従来比較的優れたものとして知られているＴＮＦよ
りも優れた電子輸送性を示し、電子写真感光体の電子輸
送材として有用である。例えば、導電性支持体上に電荷
発生層を設けた後、上記フルオレン誘導体を成膜性の樹
脂と共に塗布して電荷輸送層を形成させると、優れた電
子写真特性を有する正帯電用電子写真感光体を製造する
ことができる。 EFFECT OF THE INVENTION The fluorene derivative represented by the above general formula (I) of the present invention exhibits an electron transporting property superior to that of TNF which is conventionally known to be relatively excellent, and is useful as an electron transporting material of an electrophotographic photoreceptor. It is useful. For example, when a charge generation layer is provided on a conductive support and then the fluorene derivative is applied together with a film-forming resin to form a charge transport layer, a positive charging electrophotographic photosensitive material having excellent electrophotographic characteristics is obtained. The body can be manufactured.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｇ０３Ｇ 5/06 ３１４ Ｂ 9221−2Ｈ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Office reference number FI technical display location G03G 5/06 314 B 9221-2H
Claims (1)
は水素原子、ニトロ基又はアルコキシカルボニル基を表
わし、Ｒ３及びＲ４は、それぞれ水素原子又はアルキル
基を表わす）1. A fluorene derivative represented by the following general formula. (In the formula, R 1 represents a hydrogen atom or a phenyl group, and R 2
Represents a hydrogen atom, a nitro group or an alkoxycarbonyl group, and R 3 and R 4 each represent a hydrogen atom or an alkyl group)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1087860A JPH0657689B2 (en) | 1989-04-10 | 1989-04-10 | Fluorene derivative |
| US07/506,602 US5075487A (en) | 1988-11-16 | 1990-04-10 | Fluorene derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1087860A JPH0657689B2 (en) | 1989-04-10 | 1989-04-10 | Fluorene derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02268146A JPH02268146A (en) | 1990-11-01 |
| JPH0657689B2 true JPH0657689B2 (en) | 1994-08-03 |
Family
ID=13926640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1087860A Expired - Fee Related JPH0657689B2 (en) | 1988-11-16 | 1989-04-10 | Fluorene derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0657689B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100450188B1 (en) * | 1996-12-04 | 2004-12-03 | 삼성에스디아이 주식회사 | Electron receptor for color display panel light conducting layer, especially including fluorenone derivative |
| JP5289979B2 (en) * | 2007-07-18 | 2013-09-11 | 出光興産株式会社 | Material for organic electroluminescence device and organic electroluminescence device |
-
1989
- 1989-04-10 JP JP1087860A patent/JPH0657689B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02268146A (en) | 1990-11-01 |
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