JPH0426659A - Fluorine-containing n,n,n',n'-tetraarylbenzidine derivative and production thereof - Google Patents
Fluorine-containing n,n,n',n'-tetraarylbenzidine derivative and production thereofInfo
- Publication number
- JPH0426659A JPH0426659A JP2129149A JP12914990A JPH0426659A JP H0426659 A JPH0426659 A JP H0426659A JP 2129149 A JP2129149 A JP 2129149A JP 12914990 A JP12914990 A JP 12914990A JP H0426659 A JPH0426659 A JP H0426659A
- Authority
- JP
- Japan
- Prior art keywords
- fluorinated
- group
- alkyl group
- alkoxy group
- carbon atoms
- 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.)
- Granted
Links
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims description 13
- 229910052731 fluorine Inorganic materials 0.000 title claims description 13
- 239000011737 fluorine Substances 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 28
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims 4
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 10
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 abstract description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 6
- 150000001555 benzenes Chemical class 0.000 abstract description 5
- 229910052802 copper Inorganic materials 0.000 abstract description 4
- 239000010949 copper Substances 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- 150000007514 bases Chemical class 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 3
- -1 3-trifluoromethylphenyl Chemical group 0.000 abstract description 2
- 229910052794 bromium Inorganic materials 0.000 abstract description 2
- 229910052740 iodine Inorganic materials 0.000 abstract description 2
- 239000011368 organic material Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- UTLZBWAGLRNNAY-UHFFFAOYSA-J thorium(4+);dicarbonate Chemical compound [Th+4].[O-]C([O-])=O.[O-]C([O-])=O UTLZBWAGLRNNAY-UHFFFAOYSA-J 0.000 description 1
- SFKTYEXKZXBQRQ-UHFFFAOYSA-J thorium(4+);tetrahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[Th+4] SFKTYEXKZXBQRQ-UHFFFAOYSA-J 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】 〈産業上の利用分野〉 本発明は、新規な化合物である念フッ素Ｎ、Ｎ。[Detailed description of the invention] <Industrial application field> The present invention is directed to novel compounds such as fluorine N and N.
Ｎ’ Ｎ’ −テトラアリールベンジジン誘導体およ
びその製造方法に関する。さらに詳しく述べれば、先導
電性有機Ｈ料として有用な新規な化合物である含フッ素
Ｎ、Ｎ、Ｎ’ 、Ｎ’ −テトラアリールベンジジン誘
導体およびその製造方法に関する。The present invention relates to N'N'-tetraarylbenzidine derivatives and methods for producing the same. More specifically, the present invention relates to a fluorine-containing N,N,N',N'-tetraarylbenzidine derivative, which is a new compound useful as a leading conductive organic H material, and a method for producing the same.
〈従来の技術〉
本発明の含フッ素Ｎ、Ｎ、Ｎ’ 、Ｎ’ −テトラアリ
ールベンジジン誘導体は、いかなる文献にも報告されて
いない新規な化合物である。<Prior Art> The fluorine-containing N,N,N',N'-tetraarylbenzidine derivative of the present invention is a novel compound that has not been reported in any literature.
〈発明が解決しようとする課題〉
本発明の第一の目的は、光導電性何機月料として有用な
新規な化合物である含フッ素Ｎ、 Ｎ、 Ｎ、Ｎ′−テ
トラアリールベンジジン誘導体を提供することにある。<Problems to be Solved by the Invention> The first object of the present invention is to provide a fluorine-containing N,N,N,N'-tetraarylbenzidine derivative, which is a novel compound useful as a photoconductive material. It's about doing.
本発明の第二の目的は、光導電性何機月料として有用な
新規な化合物である含フッ素Ｎ、Ｎ、Ｎ、Ｎ′−テトラ
アリールベンジジン誘導体の製造方法を提供することに
ある。A second object of the present invention is to provide a method for producing a fluorine-containing N,N,N,N'-tetraarylbenzidine derivative, which is a novel compound useful as a photoconductive material.
く課題を解決するための手段〉
前記諸ｌ」的は、下記の一般式（Ｉ）
（ただし、式中、Ｒ１は炭素数が１〜３のアルキル基、
フッ素化アルキル基、アルコキシ基およびフッ素化アル
コキシ基よりなる群から選ばれた１種のものであり、Ｒ
２は水素、炭素数が１〜３のアルキル基、フッ素化アル
キル基、アルコキシ基およびフッ素化アルコキシ基より
なる群から選ばれた１種のものであり、Ｒ，およびＲ２
のいずれか一つ以−４ユは炭素数か１〜３のフッ素化ア
ルキル基またはフッ素化アルコキシ基を表す）で示され
る含フッ素Ｎ、Ｎ、Ｎ’ 、Ｎ’ −テトラアリールベ
ンジジン誘導体により達成される。Means for Solving the Problems> The above items are represented by the following general formula (I) (wherein R1 is an alkyl group having 1 to 3 carbon atoms,
One type selected from the group consisting of a fluorinated alkyl group, an alkoxy group, and a fluorinated alkoxy group, and R
2 is hydrogen, one type selected from the group consisting of an alkyl group having 1 to 3 carbon atoms, a fluorinated alkyl group, an alkoxy group, and a fluorinated alkoxy group, R, and R2
Achieved by a fluorine-containing N, N, N', N'-tetraarylbenzidine derivative represented by one or more of the following (-4 represents a fluorinated alkyl group or a fluorinated alkoxy group having 1 to 3 carbon atoms) be done.
本発明の一般式（Ｉ）で示される含フッ素Ｎ。The fluorine-containing N represented by the general formula (I) of the present invention.
Ｎ、Ｎ’ 、Ｎ’ −テトラアリールベンジジン誘導体
は、以下の方法により製造することができる。N,N',N'-tetraarylbenzidine derivatives can be produced by the following method.
下記の一般式（ｎ）
（ただし、式中、Ｒ１は炭素数が１〜３のアルキル基、
フッ素化アルキル基、アルコキシ基またはフッ素化アル
コキシ基を示す）で示されるベンジジン誘導体と下記の
一般式（ＩＩＩ）
１ン９
（ただし、式中、Ｒ２−は水素、炭素数が１〜３のアル
キル基、フッ素化アルキル基、アルコキシ基およびフッ
素化アルコキシ基よりなる群から選はれた１種のもので
あり、Ｘはヨウ素または臭素を表す）で示されるハロゲ
ン化ベンゼン誘導体とを銅系触媒および塩基性化合物の
存在下で反応させることにより製造することができる。The following general formula (n) (wherein, R1 is an alkyl group having 1 to 3 carbon atoms,
A benzidine derivative represented by a fluorinated alkyl group, an alkoxy group, or a fluorinated alkoxy group) and the following general formula (III) 1-9 (wherein, R2- is hydrogen, an alkyl group having 1 to 3 carbon atoms) a halogenated benzene derivative selected from the group consisting of a fluorinated alkyl group, a fluorinated alkyl group, an alkoxy group, and a fluorinated alkoxy group, where X represents iodine or bromine) using a copper-based catalyst and It can be produced by reacting in the presence of a basic compound.
く作用〉
本発明によれは、−形式（１）で示される劇フッ素Ｎ、
Ｎ、Ｎ’ 、Ｎ’ −テＩ・ラアリールベンジジン誘導
体は、−形式（ＩＩ ）で示されるベンジジン誘導体と
、−形式（ＩＩＩ）で示されるハロゲン化ベンゼン誘導
体との反応により製造される。該ベンジジン誘導体およ
びハロゲン化ベンゼン誘導体は、通常化学世論量を使用
すれはよいが、反応の促進、収率ならびに経済性を考慮
して、ハロゲン化ベンゼン誘導体は、ベンジジン誘導体
に対して化学量論量の０． ２〜１０倍量、好ましくは
０゜５〜３倍量の範囲で使用すればよい。According to the present invention, - a fluorine N represented by the form (1),
The N,N',N'-teI.laarylbenzidine derivative is produced by the reaction of a benzidine derivative represented by the -format (II) and a halogenated benzene derivative represented by the -format (III). The benzidine derivative and the halogenated benzene derivative may be used in stoichiometric amounts in general, but in consideration of reaction promotion, yield, and economy, the halogenated benzene derivative is used in a stoichiometric amount relative to the benzidine derivative. 0. It may be used in an amount of 2 to 10 times, preferably 0.5 to 3 times.
本発明で使用される銅系触媒としては、例えは銅粉末、
酸化銅あるいはハロゲン化銅等の銅化合物を挙げること
かできる。その使用量は、−形式（ＩＩ ）で示される
ベンジジン誘導体に対してモル比で０．２〜１０倍量、
好ましくは０゜５〜３倍量である。Examples of the copper-based catalyst used in the present invention include copper powder,
Copper compounds such as copper oxide or copper halide may be mentioned. The amount used is -0.2 to 10 times the molar ratio of the benzidine derivative represented by the format (II);
Preferably it is 0.5 to 3 times the amount.
本発明で使用される塩基性化合物としては、アルカリ金
属の水酸化物または炭酸塩類が挙げられ、具体的には水
酸化すトリウム、水酸化カリウム、炭酸すトリウム、炭
酸カリウム等を挙げることかできる。その使用量は、−
形式（ＩＩ ）で示されるベンジジン誘導体に対してモ
ル比で１〜２０倍量、好ましくは１．５〜５倍量である
。Examples of the basic compound used in the present invention include alkali metal hydroxides or carbonates, and specific examples include thorium hydroxide, potassium hydroxide, thorium carbonate, potassium carbonate, etc. . Its usage is −
The molar ratio is 1 to 20 times, preferably 1.5 to 5 times, the amount of the benzidine derivative represented by format (II).
本発明においては、必要ならば反応溶媒の共存化で行う
が、例えば二）・ロベンゼン、ジクロルベンゼン、キノ
リン、Ｎ、Ｎ−ジメチルホルムアミド、ジメチルスルホ
キシド、Ｎ−メチルピロリドン、１，３−ジメチル−２
−イミダゾリジノン等の溶媒を単独もしくは組合わせて
使用することができる。その使用量は、−形式（ＩＩ）
で示されるベンジジン誘導体に対して重量比で０．２〜
１０倍量、好ましくは０．５〜５倍量の範囲で使用すれ
ばよい。In the present invention, if necessary, the reaction solvent is coexisted with, for example, 2) lobenzene, dichlorobenzene, quinoline, N,N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, 1,3-dimethyl- 2
-Solvents such as imidazolidinone can be used alone or in combination. Its usage is - form (II)
A weight ratio of 0.2 to the benzidine derivative represented by
It may be used in an amount of 10 times, preferably 0.5 to 5 times.
この際、反応温度を１２０〜２８０℃、好ましくは１５
０〜２５０°Ｃの範囲内で行われ、反応時間は２〜４８
峙間である。At this time, the reaction temperature is 120 to 280°C, preferably 15°C.
It is carried out within the range of 0 to 250 °C, and the reaction time is 2 to 48 °C.
It is Ichima.
このようにして製造される本発明に関わる新規な化合物
である含フツ素テトラアリールベンジジン誘導体を表−
１に例示したが、もとよりこれらに限定されるものでは
ない。The fluorine-containing tetraarylbenzidine derivatives, which are novel compounds related to the present invention produced in this way, are shown below.
1, but is not limited to these.
表 〈実施例〉 次に実施例により本発明について詳細に説明するが、 もとより本発明はこれらに限定されるものではない。table <Example> Next, the present invention will be explained in detail with reference to Examples. Of course, the present invention is not limited to these.
実施例
温度計、
分水器付凝縮器および撹拌機装置３０
０ｍｌガラス製丸底フラスコに９９．５％の０トリジン
１３．９ｇ、９９．４％のｍ−ヨードベンシトリフルオ
ライド１０６．７ｇ・、炭酸カリウム２７ｇ・および銅
粉４ｇを仕込み、１８０℃で２４時間紺：持した。その
際、反応で生成する水は、分水器により反応系外へ取り
出した。Example Thermometer, condenser with water separator, and stirrer device 30 In a 0 ml glass round bottom flask, 13.9 g of 99.5% O-tolidine, 106.7 g of 99.4% m-iodobencitrifluoride, 27 g of potassium carbonate and 4 g of copper powder were charged and kept at 180° C. for 24 hours. At that time, water produced in the reaction was taken out of the reaction system using a water separator.
反応終了後、内容物をトルエン２００ｍ１に希釈し、不
溶解物を濾別して得られたトルエン溶液を減圧下で濃縮
して褐色の油状物を得た。After the reaction was completed, the contents were diluted with 200 ml of toluene, and the toluene solution obtained by filtering off insoluble matter was concentrated under reduced pressure to obtain a brown oil.
次いで、褐色の油状物をカラムクロマトグラフィー（ア
ルミナ／トルエン）で精製し、得られた淡黄色油状物を
ｎ−ヘキサジで再結晶を行って純度９９．８％の３，３
′ −ジメチル−Ｎ、 Ｎ、 ＮＮ′−テトラキス（３
−１−リフルオロメチルフェニル）−［１，１’−ビフ
ェニル］−４，４−ジアミンの白色結晶２８．０ｇを得
た（牧牛５４．４％）。Next, the brown oil was purified by column chromatography (alumina/toluene), and the pale yellow oil obtained was recrystallized with n-hexadiene to obtain 3,3 with a purity of 99.8%.
' -dimethyl-N, N, NN'-tetrakis (3
28.0 g of white crystals of -1-lifluoromethylphenyl)-[1,1'-biphenyl]-4,4-diamine were obtained (54.4% from cattle).
融 点 １５２．８′Ｃ
元素分析値（Ｃ４２１１２８Ｆ１２Ｎ２として計算）Ｃ
ＩＩ ｌ” Ｎ
計算値 ６３．９６％３．５８％２８．９Ｌ％３．５５
％実／１１り値 ６３．８０％３．７２％２８．８０％
３．６５％第１図に、３，３′ −ジメチル−Ｎ、 Ｎ
、 Ｎ’Ｎ′−テトラキス（３−１−リフルオロメチル
フェニル）−［１，１’ −ビフェニル］−４，４’ジ
アミンの赤外線吸収スペクトル（ＫＢｒ錠剤法）を示し
た。Melting point 152.8'C Elemental analysis value (calculated as C421128F12N2)C
II l”N Calculated value 63.96%3.58%28.9L%3.55
%Actual/11 value 63.80%3.72%28.80%
3.65% Figure 1 shows 3,3'-dimethyl-N, N
, shows an infrared absorption spectrum (KBr tablet method) of N'N'-tetrakis(3-1-lifluoromethylphenyl)-[1,1'-biphenyl]-4,4'diamine.
〈発明の効果〉
本発明に関わる新規な化合物である含フツ素テトラアリ
ールベンジジン誘導体は、光導電性向゛機材料として有
用な化合物である。<Effects of the Invention> The fluorine-containing tetraarylbenzidine derivative, which is a novel compound related to the present invention, is a compound useful as a photoconductive organic material.
第１図は、実施例１で得られた３、３′ −ジメチル−
Ｎ、 Ｎ、 Ｎ’ 、 Ｎ’−テトラキス（３−１−リ
フルオロメチルフェニル：）−［１，１’ −ビフェ
ニル］ −４，４’ −ジアミンの赤外線吸収スペクト
ルを示したものである。
］２Figure 1 shows the 3,3'-dimethyl-
It shows the infrared absorption spectrum of N, N, N', N'-tetrakis(3-1-lifluoromethylphenyl:)-[1,1'-biphenyl]-4,4'-diamine. ]2
Claims (2)
、フッ素化アルキル基、アルコキシ基およびフッ素化ア
ルコキシ基よりなる群から選ばれた１種のものであり、
Ｒ＿２は水素、炭素数が１〜３のアルキル基、フッ素化
アルキル基、アルコキシ基およびフッ素化アルコキシ基
よりなる群から選ばれた１種のものであり、Ｒ＿１およ
びＲ＿２のいずれか一つ以上は炭素数が１〜３のフッ素
化アルキル基またはフッ素化アルコキシ基を表す）で示
される含フッ素Ｎ，Ｎ，Ｎ′，Ｎ′−テトラアリールベ
ンジジン誘導体。(1) The following general formula I ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (I) (In the formula, R_1 is an alkyl group having 1 to 3 carbon atoms, a fluorinated alkyl group, an alkoxy group, and a fluorinated alkoxy It is one type selected from the group consisting of the following:
R_2 is one selected from the group consisting of hydrogen, an alkyl group having 1 to 3 carbon atoms, a fluorinated alkyl group, an alkoxy group, and a fluorinated alkoxy group, and at least one of R_1 and R_2 is A fluorine-containing N,N,N',N'-tetraarylbenzidine derivative represented by a fluorinated alkyl group or a fluorinated alkoxy group having 1 to 3 carbon atoms.
、フッ素化アルキル基、アルコキシ基またはフッ素化ア
ルコキシ基を表す）で示されるベンジジン誘導体と下記
の一般式（III） ▲数式、化学式、表等があります▼（III） （ただし、式中、Ｒ＿２は水素、炭素数が１〜３のアル
キル基、フッ素化アルキル基、アルコキシ基およびフッ
素化アルコキシ基よりなる群から選ばれた１種のもので
あり、Ｘはヨウ素または臭素を表す）で示されるハロゲ
ン化ベンゼン誘導体とを銅系触媒および塩基性化合物の
存在下で反応させることを特徴とする下記の一般式（
I ） ▲数式、化学式、表等があります▼（ I ） （ただし、式中、Ｒ＿１は炭素数が１〜３のアルキル基
、フッ素化アルキル基、アルコキシ基およびフッ素化ア
ルコキシ基よりなる群から選ばれた１種のものであり、
Ｒ＿２は水素、炭素数が１〜３のアルキル基、フッ素化
アルキル基、アルコキシ基およびフッ素化アルコキシ基
よりなる群から選ばれた１種のものであり、Ｒ＿１およ
びＲ＿２のいずれか一つ以上は、炭素数が１〜３のフッ
素化アルキル基またはフッ素化アルコキシ基を表す）で
示される含フッ素Ｎ，Ｎ，Ｎ′，Ｎ′−テトラアリール
ベンジジン誘導体の製造方法。(2) The following general formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) (However, in the formula, R_1 is an alkyl group having 1 to 3 carbon atoms, a fluorinated alkyl group, an alkoxy group, or fluorine represents alkoxy group) and the general formula (III) below ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (III) (However, in the formula, R_2 is hydrogen, alkyl having 1 to 3 carbon atoms a halogenated benzene derivative represented by a group consisting of a fluorinated alkyl group, a fluorinated alkyl group, an alkoxy group, and a fluorinated alkoxy group, where The following general formula (
I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (However, in the formula, R_1 is selected from the group consisting of an alkyl group having 1 to 3 carbon atoms, a fluorinated alkyl group, an alkoxy group, and a fluorinated alkoxy group. It is one type of
R_2 is one selected from the group consisting of hydrogen, an alkyl group having 1 to 3 carbon atoms, a fluorinated alkyl group, an alkoxy group, and a fluorinated alkoxy group, and at least one of R_1 and R_2 is represents a fluorinated alkyl group or a fluorinated alkoxy group having 1 to 3 carbon atoms).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2129149A JP2863264B2 (en) | 1990-05-21 | 1990-05-21 | Fluorinated N, N, N ', N'-tetraarylbenzidine derivatives and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2129149A JP2863264B2 (en) | 1990-05-21 | 1990-05-21 | Fluorinated N, N, N ', N'-tetraarylbenzidine derivatives and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0426659A true JPH0426659A (en) | 1992-01-29 |
| JP2863264B2 JP2863264B2 (en) | 1999-03-03 |
Family
ID=15002353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2129149A Expired - Fee Related JP2863264B2 (en) | 1990-05-21 | 1990-05-21 | Fluorinated N, N, N ', N'-tetraarylbenzidine derivatives and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2863264B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998006692A1 (en) * | 1996-08-12 | 1998-02-19 | Celgene Corporation | Novel immunotherapeutic agents and their use in the reduction of cytokine levels |
| JP2004217638A (en) * | 2002-12-27 | 2004-08-05 | Hodogaya Chem Co Ltd | Method for producing material for electronic product |
| JP4480827B2 (en) * | 1998-12-25 | 2010-06-16 | 保土谷化学工業株式会社 | Method for producing triarylamine derivative |
-
1990
- 1990-05-21 JP JP2129149A patent/JP2863264B2/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998006692A1 (en) * | 1996-08-12 | 1998-02-19 | Celgene Corporation | Novel immunotherapeutic agents and their use in the reduction of cytokine levels |
| JP4480827B2 (en) * | 1998-12-25 | 2010-06-16 | 保土谷化学工業株式会社 | Method for producing triarylamine derivative |
| JP2004217638A (en) * | 2002-12-27 | 2004-08-05 | Hodogaya Chem Co Ltd | Method for producing material for electronic product |
| JP4536365B2 (en) * | 2002-12-27 | 2010-09-01 | 保土谷化学工業株式会社 | Manufacturing method of electronic product material |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2863264B2 (en) | 1999-03-03 |
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