JP2002212181A - Method for producing benzazole group-containing triazine compound - Google Patents
Method for producing benzazole group-containing triazine compoundInfo
- Publication number
- JP2002212181A JP2002212181A JP2001014298A JP2001014298A JP2002212181A JP 2002212181 A JP2002212181 A JP 2002212181A JP 2001014298 A JP2001014298 A JP 2001014298A JP 2001014298 A JP2001014298 A JP 2001014298A JP 2002212181 A JP2002212181 A JP 2002212181A
- Authority
- JP
- Japan
- Prior art keywords
- group
- producing
- triazine compound
- general formula
- acid
- 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
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明はベンゾアゾール基含
有トリアジン系化合物の製造方法に関する。詳しくは本
発明は電界発光素子などの用途に有用なベンゾアゾール
基含有トリアジン系化合物の新規な製造方法に関する。The present invention relates to a method for producing a triazine compound containing a benzoazole group. More specifically, the present invention relates to a novel method for producing a benzoazole group-containing triazine-based compound useful for applications such as electroluminescent devices.
【０００２】[0002]
【従来の技術】特開平７−１５７４７３号公報に下記構
造式：2. Description of the Related Art JP-A-7-157473 discloses the following structural formula:
【０００３】[0003]
【化３】 Embedded image
【０００４】（式中、Ｘは酸素原子、硫黄原子又はＮ−
ＣＨ3基を表す。）で表されるトリアジン系化合物が電
界発光素子用の材料として有用であることが報告されて
おり、また、それらの製造方法として下記構造式：Wherein X is an oxygen atom, a sulfur atom or N-
Represents a CH 3 group. It has been reported that the triazine-based compound represented by the formula (1) is useful as a material for an electroluminescent device.
【０００５】[0005]
【化４】 Embedded image
【０００６】（式中、Ｘは酸素原子、硫黄原子又はＮ−
ＣＨ3基を表す。）で表される２−（４−ヨードフェニ
ル）ベンズアゾール類とシアヌル酸クロリドとをｎ−ブ
チルリチウムの存在下で−７０℃で反応させることが記
載されている。Wherein X is an oxygen atom, a sulfur atom or N-
Represents a CH 3 group. The reaction of 2- (4-iodophenyl) benzazoles represented by the formula (1) with cyanuric chloride at -70 ° C in the presence of n-butyllithium is described.
【０００７】[0007]
【発明が解決しようとする課題】上記の製造方法におい
ては変異原性化合物であるシアヌル酸クロリド及び発火
性物質であるｎ−ブチルリチウムを使用するために安全
上の問題があり、また、−７０℃という低温が必要であ
ることから実用的に有利な製造方法であるとは言えな
い。本発明の目的は上記トリアジン系化合物を製造する
ための安全でかつ実用的に有利な方法を提供することに
ある。In the above-mentioned production method, there are safety problems due to the use of the mutagenic compound cyanuric chloride and the ignitable substance n-butyllithium. Since a low temperature of ° C is required, it cannot be said that this is a practically advantageous production method. An object of the present invention is to provide a safe and practically advantageous method for producing the above triazine-based compound.
【０００８】[0008]
【課題を解決するための手段】即ち本発明の要旨は、下
記一般式（Ｉ）：That is, the gist of the present invention is that of the following general formula (I):
【０００９】[0009]
【化５】 Embedded image
【００１０】（式中、Ｘは酸素原子、硫黄原子又はＮ−
Ｒ基を表し、Ｒはアルキル基又はアリール基を表す。ま
た、芳香環Ａは任意の置換基を有していてもよい）で表
されるニトリル化合物を強酸の存在下に三量化反応させ
て下記一般式（II）：Wherein X is an oxygen atom, a sulfur atom or N-
R represents an R group, and R represents an alkyl group or an aryl group. Further, the nitrile compound represented by the formula (II) may be obtained by trimerizing a nitrile compound represented by the following formula (II):
【００１１】[0011]
【化６】 Embedded image
【００１２】（式中、Ｘ及びＡは上記一般式（Ｉ）にお
けると同じ）で表されるトリアジン系化合物を生成させ
ることを特徴とするベンゾアゾール基含有トリアジン系
化合物の製造方法、に存する。(Wherein X and A are the same as those in the general formula (I)), wherein the method comprises the step of producing a triazine compound having a benzoazole group.
【００１３】[0013]
【発明の実施の形態】以下に本発明の実施の形態につき
詳細に説明する。本発明方法においては、上記ニトリル
化合物（Ｉ）を強酸の存在下に三量化反応させてトリア
ジン系化合物（II）を生成させる。原料の上記ニトリル
化合物（Ｉ）は、例えば下記式（III)：Embodiments of the present invention will be described below in detail. In the method of the present invention, the nitrile compound (I) is subjected to a trimerization reaction in the presence of a strong acid to produce a triazine compound (II). The nitrile compound (I) as a raw material is, for example, represented by the following formula (III):
【００１４】[0014]
【化７】 Embedded image
【００１５】（式中、Ｘ及びＡは前記一般式（Ｉ）にお
けると同じ）で表されるオルトアミノフェノール類、オ
ルトアミノチオフェノール類あるいはオルトフェニレン
ジアミン類とｐ−シアノ安息香酸クロリドとから下記式
（IV）：(Wherein X and A are the same as those in the general formula (I)) from the following formulas from orthoaminophenols, orthoaminothiophenols or orthophenylenediamines and p-cyanobenzoic acid chloride: Formula (IV):
【００１６】[0016]
【化８】 Embedded image
【００１７】（式中、Ｘ及びＡは前記一般式（Ｉ）にお
けると同じ）で表されるアミド化合物を製造し、次いで
該アミド化合物（IV）にｐ−トルエンスルホン酸、塩化
亜鉛などの脱水剤を作用させることにより製造すること
が出来る。なお、前記式（Ｉ）〜（IV）の芳香環Ａの置
換基の種類としては、置換されていてもよいアルキル
基、置換されていてもよいアルコキシ基、シアノ基、ニ
トロ基、ヒドロキシ基、アシル基、アリール基、カルボ
キシル基、アルコキシカルボニル基、カルバモイル基、
アルキルカルバモイル基、ジアルキルカルバモイル基、
アシルオキシ基、ジアルキルアミノ基、ジアリールアミ
ノ基、アシルアミノ基、スルホニルアミノ基、アルキル
スルホニル基、アルコキシスルホニル基、スルファモイ
ル基、アルキルスルファモイル基、ジアルキルスルファ
モイル基などが挙げられる。これらの置換基の数は１〜
４個の範囲内で可能である。有利な置換基としては、低
級アルキル基、低級アルコキシ基などが挙げられる。(Wherein X and A are the same as those in the general formula (I)), and then the amide compound (IV) is dehydrated with p-toluenesulfonic acid, zinc chloride or the like. It can be produced by acting an agent. The types of the substituent of the aromatic ring A in the formulas (I) to (IV) include an alkyl group which may be substituted, an alkoxy group which may be substituted, a cyano group, a nitro group, a hydroxy group, Acyl group, aryl group, carboxyl group, alkoxycarbonyl group, carbamoyl group,
Alkylcarbamoyl group, dialkylcarbamoyl group,
Examples include an acyloxy group, a dialkylamino group, a diarylamino group, an acylamino group, a sulfonylamino group, an alkylsulfonyl group, an alkoxysulfonyl group, a sulfamoyl group, an alkylsulfamoyl group, and a dialkylsulfamoyl group. The number of these substituents is 1 to
Possible within four ranges. Advantageous substituents include lower alkyl groups, lower alkoxy groups, and the like.
【００１８】上記強酸としては特に限定されないが、反
応活性の点からスルホン酸を用いるのが好適である。ス
ルホン酸類としては、例えばフルオロスルホン酸、クロ
ロスルホン酸等のハロゲノスルホン酸類；トリフルオロ
メタンスルホン酸等のフルオロアルカンスルホン酸類そ
の他の脂肪族スルホン酸類；ベンゼンスルホン酸、トル
エンスルホン酸、ナフタレンスルホン酸等の芳香族スル
ホン酸類；スチレン系スルホン酸型陽イオン交換樹脂等
のスルホン酸型陽イオン交換樹脂等が挙げられ、それら
の中ではフルオロスルホン酸、クロロスルホン酸等のハ
ロゲノスルホン酸類並びにトリフルオロメタンスルホン
酸等のフルオロアルカンスルホン酸類がより好適であ
る。The strong acid is not particularly limited, but sulfonic acid is preferably used from the viewpoint of reaction activity. Examples of the sulfonic acids include halogenosulfonic acids such as fluorosulfonic acid and chlorosulfonic acid; fluoroalkanesulfonic acids such as trifluoromethanesulfonic acid and other aliphatic sulfonic acids; aromatics such as benzenesulfonic acid, toluenesulfonic acid, and naphthalenesulfonic acid. Group sulfonic acids; sulfonic acid type cation exchange resins such as styrene type sulfonic acid type cation exchange resins, etc. Among them, halogenosulfonic acids such as fluorosulfonic acid and chlorosulfonic acid and trifluoromethanesulfonic acid etc. Fluoroalkanesulfonic acids are more preferred.
【００１９】本発明の三量化反応の実施方法は特に限定
されないが、上記強酸が液体である場合には、通常、上
記の強酸自身を溶媒として用い、常温で反応させた後、
反応液を氷水中に排出し、析出する目的物を濾取し、必
要に応じて再結晶、クロマトグラフィー、昇華などの方
法で精製するなどの方法を採用することができる。The method for carrying out the trimerization reaction of the present invention is not particularly limited. When the strong acid is a liquid, the strong acid itself is usually used as a solvent and reacted at room temperature.
A method in which the reaction solution is discharged into ice water, the target substance that precipitates is collected by filtration, and if necessary, purified by a method such as recrystallization, chromatography, or sublimation can be used.
【００２０】[0020]
【実施例】以下、実施例により本発明の具体的態様を詳
細に説明するが、本発明は、その要旨を越えない限り、
以下の実施例によって限定されるものではない。 実施例１ ２−（ｐ−シアノフェニル）ベンゾオキサゾール２．８
ｇをトリフルオロメタンスルホン酸２５ｇ中に仕込み、
２５〜３０℃で５時間撹拌した後、氷水中に排出し、析
出結晶を濾過し、水洗し、乾燥して淡黄色結晶３．６ｇ
を得た。この結晶をジメチルホルムアミド（ＤＭＦ）か
ら再結晶精製して淡黄色結晶１．５ｇを得た。得られた
結晶は薄層クロマトグラフィーで単一スポットを示し、
マススペクトル測定の結果、親イオンピークとしてｍ／
ｚ＝６６０が検出され、下記式の構造の化合物であるこ
とが確認された。EXAMPLES Hereinafter, specific embodiments of the present invention will be described in detail with reference to Examples.
It is not limited by the following examples. Example 1 2- (p-cyanophenyl) benzoxazole 2.8
g in 25 g of trifluoromethanesulfonic acid,
After stirring at 25 to 30 ° C. for 5 hours, the mixture is discharged into ice water, and the precipitated crystals are filtered, washed with water, and dried to obtain 3.6 g of pale yellow crystals.
I got The crystals were recrystallized and purified from dimethylformamide (DMF) to obtain 1.5 g of pale yellow crystals. The resulting crystals show a single spot by thin layer chromatography,
As a result of the mass spectrum measurement, m /
z = 660 was detected, and it was confirmed that it was a compound of the structure of the following formula.
【００２１】[0021]
【化９】 Embedded image
【００２２】この化合物の吸収スペクトル及び蛍光スペ
クトルの測定結果は下記の通りであり、強い青色の蛍光
を示した。The measurement results of the absorption spectrum and the fluorescence spectrum of this compound are as follows, and showed strong blue fluorescence.
【００２３】[0023]
【表１】 吸収スペクトル（溶媒：塩化メチレン） λｍａｘ：３４０ｎｍ（ε：１５５，０００） 蛍光スペクトル（溶媒：塩化メチレン） λｍａｘ：４０７ｎｍTable 1 Absorption spectrum (solvent: methylene chloride) λmax: 340 nm (ε: 155,000) Fluorescence spectrum (solvent: methylene chloride) λmax: 407 nm
【００２４】なお、原料の２−（ｐ−シアノフェニル）
ベンゾオキサゾールは以下の方法で合成した。ｐ−シア
ノベンゾイルクロリド９．５ｇをＮ，Ｎ−ジメチルホル
ムアミド５０ｍｌ中に仕込み、ｏ−アミノフェノール
６．６ｇを添加し、１００〜１１０℃で１時間反応さ
せ、室温まで冷却した後、水２０ｍｌを添加し、析出結
晶を濾過し、水洗し、乾燥して白色結晶７．０ｇを得
た。この結晶３．６ｇをトルエン１００ｍｌ中に仕込
み、ｐ−トルエンスルホン酸０．２ｇを添加し、還流下
３時間反応させた後、溶媒を留去し、残渣をメタノール
で洗浄し、乾燥して白色結晶２．９ｇを得た。上記結晶
は薄層クロマトグラフィーで単一スポットを示し、マス
スペクトル測定の結果、親イオンピークとしてｍ／ｚ＝
２２０が検出され、２−（ｐ−シアノフェニル）ベンゾ
オキサゾールであることが確認された。The starting material, 2- (p-cyanophenyl)
Benzoxazole was synthesized by the following method. 9.5 g of p-cyanobenzoyl chloride was charged into 50 ml of N, N-dimethylformamide, 6.6 g of o-aminophenol was added, and the mixture was reacted at 100 to 110 ° C. for 1 hour. After cooling to room temperature, 20 ml of water was added. The precipitated crystals were filtered, washed with water and dried to obtain 7.0 g of white crystals. 3.6 g of these crystals were charged in 100 ml of toluene, 0.2 g of p-toluenesulfonic acid was added, and the mixture was reacted under reflux for 3 hours. The solvent was distilled off, and the residue was washed with methanol and dried to give white. 2.9 g of crystals were obtained. The crystal shows a single spot by thin layer chromatography, and as a result of mass spectrum measurement, m / z =
220 was detected, and it was confirmed that it was 2- (p-cyanophenyl) benzoxazole.
【００２５】実施例２ ２−（ｐ−シアノフェニル）ベンゾチアゾール３．２ｇ
をトリフルオロメタンスルホン酸２５ｇ中に仕込み、２
５〜３０℃で５時間撹拌した後、氷水中に排出し、析出
結晶を濾過し、水洗し、乾燥して淡黄色結晶３．８ｇを
得た。この結晶をＤＭＦから再結晶精製して淡黄色結晶
１．６ｇを得た。得られた結晶は薄層クロマトグラフィ
ーで単一スポットを示し、マススペクトル測定の結果、
親イオンピークとしてｍ／ｚ＝７０８が検出され、下記
式の構造の化合物であることが確認された。Example 2 3.2 g of 2- (p-cyanophenyl) benzothiazole
In 25 g of trifluoromethanesulfonic acid, and 2
After stirring at 5 to 30 ° C. for 5 hours, the mixture was discharged into ice water, and the precipitated crystals were filtered, washed with water and dried to obtain 3.8 g of pale yellow crystals. The crystals were recrystallized and purified from DMF to obtain 1.6 g of pale yellow crystals. The obtained crystals show a single spot by thin layer chromatography, and as a result of mass spectrum measurement,
M / z = 708 was detected as the parent ion peak, and it was confirmed that the compound had the structure of the following formula.
【００２６】[0026]
【化１０】 Embedded image
【００２７】この化合物の吸収スペクトル及び蛍光スペ
クトルの測定結果は下記の通りであり、強い青色の蛍光
を示した。The measurement results of the absorption spectrum and the fluorescence spectrum of this compound are as follows, and showed strong blue fluorescence.
【００２８】[0028]
【表２】 吸収スペクトル（溶媒：塩化メチレン） λｍａｘ：３４５ｎｍ（ε：１０４，０００） 蛍光スペクトル（溶媒：塩化メチレン） λｍａｘ：４０７ｎｍTable 2 Absorption spectrum (solvent: methylene chloride) λmax: 345 nm (ε: 104,000) Fluorescence spectrum (solvent: methylene chloride) λmax: 407 nm
【００２９】なお、原料の２−（ｐ−シアノフェニル）
ベンゾチアゾールは以下の方法で合成した。ｐ−シアノ
ベンゾイルクロリド９．５ｇをＮ，Ｎ−ジメチルホルム
アミド５０ｍｌ中に仕込み、ｏ−アミノチオフェノール
７．５ｇを添加し、１００〜１１０℃で１時間反応さ
せ、室温まで冷却した後、水２０ｍｌを添加し、析出結
晶を濾過し、水洗し、乾燥して白色結晶９．８ｇを得
た。この結晶３．８ｇをトルエン１００ｍｌ中に仕込
み、ｐ−トルエンスルホン酸０．２ｇを添加し、還流下
３時間反応させた後、溶媒を留去し、残渣をメタノール
で洗浄し、乾燥して白色結晶３．３ｇを得た。この結晶
は薄層クロマトグラフィーで単一スポットを示し、マス
スペクトル測定の結果、親イオンピークとしてｍ／ｚ＝
２３６が検出され、２−（ｐ−シアノフェニル）ベンゾ
チアゾールであることが確認された。The raw material 2- (p-cyanophenyl)
Benzothiazole was synthesized by the following method. 9.5 g of p-cyanobenzoyl chloride was charged into 50 ml of N, N-dimethylformamide, 7.5 g of o-aminothiophenol was added, the mixture was reacted at 100 to 110 ° C. for 1 hour, cooled to room temperature, and then cooled to 20 ml of water. Was added, and the precipitated crystals were filtered, washed with water and dried to obtain 9.8 g of white crystals. 3.8 g of these crystals were charged in 100 ml of toluene, 0.2 g of p-toluenesulfonic acid was added, and the mixture was reacted under reflux for 3 hours. The solvent was distilled off, and the residue was washed with methanol and dried to give white. 3.3 g of crystals were obtained. This crystal shows a single spot by thin layer chromatography, and as a result of mass spectrum measurement, m / z =
236 was detected, and it was confirmed to be 2- (p-cyanophenyl) benzothiazole.
【００３０】[0030]
【発明の効果】本発明方法により、有機電界発光素子用
材料として有用なベンゾアゾール基含有トリアジン系化
合物（II）を、安全でかつ簡単な操作により収率よく製
造することができる。According to the present invention, a benzoazole group-containing triazine compound (II) useful as a material for an organic electroluminescent device can be produced in a safe and simple operation with a high yield.
Claims (2)
Ｒはアルキル基又はアリール基を表す。また、芳香環Ａ
は任意の置換基を有していてもよい）で表されるニトリ
ル化合物を強酸の存在下に三量化反応させて下記一般式
（II）： 【化２】 （式中、Ｘ及びＡは上記一般式（Ｉ）におけると同じ）
で表されるトリアジン系化合物を生成させることを特徴
とするベンゾアゾール基含有トリアジン系化合物の製造
方法。1. The following general formula (I): (Wherein, X represents an oxygen atom, a sulfur atom or an NR group,
R represents an alkyl group or an aryl group. In addition, aromatic ring A
May optionally have a substituent), and a trimerization reaction of the nitrile compound represented by the following general formula (II): (Wherein X and A are the same as in the above general formula (I))
A process for producing a triazine compound containing a benzoazole group, characterized by producing a triazine compound represented by the formula:
記載のベンゾアゾール基含有トリアジン系化合物の製造
方法。2. The method for producing a triazine compound having a benzoazole group according to claim 1, wherein the strong acid is a sulfonic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001014298A JP2002212181A (en) | 2001-01-23 | 2001-01-23 | Method for producing benzazole group-containing triazine compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001014298A JP2002212181A (en) | 2001-01-23 | 2001-01-23 | Method for producing benzazole group-containing triazine compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2002212181A true JP2002212181A (en) | 2002-07-31 |
Family
ID=18881013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001014298A Pending JP2002212181A (en) | 2001-01-23 | 2001-01-23 | Method for producing benzazole group-containing triazine compound |
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| Country | Link |
|---|---|
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005306862A (en) * | 2004-03-25 | 2005-11-04 | Semiconductor Energy Lab Co Ltd | Triazine derivative, and light-emitting element and light emitter containing the same |
| WO2009081873A1 (en) | 2007-12-25 | 2009-07-02 | National University Corporation Nagoya University | Organic material containing oligophenylene skeleton and light-emitting device using the same |
| EP2197979A2 (en) * | 2007-10-17 | 2010-06-23 | Cheil Industries Inc. | Novel compound for organic photoelectric device and organic photoelectric device including the same |
| WO2010076991A3 (en) * | 2008-12-30 | 2010-09-10 | 제일모직 주식회사 | Novel compounds for an organic photoelectric device, and organic photoelectric device comprising same |
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