JPS61260038A - Squarylium compound - Google Patents
Squarylium compoundInfo
- Publication number
- JPS61260038A JPS61260038A JP10158085A JP10158085A JPS61260038A JP S61260038 A JPS61260038 A JP S61260038A JP 10158085 A JP10158085 A JP 10158085A JP 10158085 A JP10158085 A JP 10158085A JP S61260038 A JPS61260038 A JP S61260038A
- Authority
- JP
- Japan
- Prior art keywords
- azulene
- benz
- isopropylazulene
- isopropyl
- formula
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing alicyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/683—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings
-
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
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- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
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- C09K19/00—Liquid crystal materials
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、広範囲の溶媒に対する溶解性が良好でかつ溶
液中における極大吸収波長が７００〜９００ ｎｍの付
近にある、耐光性が良好の新規なスクアリリウム化合物
に関する。Detailed Description of the Invention (Industrial Field of Application) The present invention is directed to a novel method that has good solubility in a wide range of solvents, has a maximum absorption wavelength in the vicinity of 700 to 900 nm, and has good light resistance. related to squarylium compounds.
（従来の技術）
スクアリリウム化合物が、光導電性を示し、例えば電子
写真用感光体の電荷発生剤（特開昭４９−１０５５３６
号公報）、レーザー書き込み液晶表示用レーザー光吸収
材料（特開昭５９−１９７４８５号公報）、あるいは光
デイスク用記録材料（特開昭５６−４６２２１号、特開
昭５８−２１７７５８号及び特開昭５９−１２９９５４
号等の各公報）などとして使用さ糺ていることは知られ
ている。(Prior Art) Squarylium compounds exhibit photoconductivity and are used, for example, as charge generating agents for electrophotographic photoreceptors (Japanese Unexamined Patent Publication No. 49-105536).
JP-A-59-197485), laser-absorbing materials for laser-written liquid crystal displays (JP-A-59-197485), or recording materials for optical disks (JP-A-56-46221, JP-A-58-217758, and JP-A-Sho 58-217758) 59-129954
It is known that it is used in various publications such as No.
（発明が解決しようとする問題点）
しかしながら、従来公知のスクアリリウム化合物は、例
えばＮ−ジメチルホルムアミド、Ｎ−メチルピロリドン
、Ｎ−ジメチルアセトアミド、ホルムアミド等の非プロ
トン系極性溶媒などの限られた溶媒にのみ可溶なもので
あるばかシか、例えば特開昭５９−１２９９５４号公報
記載の化合物＆６のように溶解性の非常に乏しいものも
あるなど、溶解性上問題点のあるものであった。また、
これらの多くのものは、溶液中での極大吸収波長が半導
体レーザーの発振波長である７８０ｎｍ、８熟り國９−
から大きく外れておシ、更には耐光性が不充分で安定性
に欠ける、といった問題点のあることからも利用分野に
制限があシ、とくにレーザー光を光源とする各種情報材
料として使用するには満足できるものではなかった。(Problems to be Solved by the Invention) However, conventionally known squarylium compounds cannot be used in limited solvents such as aprotic polar solvents such as N-dimethylformamide, N-methylpyrrolidone, N-dimethylacetamide, and formamide. There are problems in terms of solubility, such as those that are only soluble, and some that have very poor solubility, such as Compound &6 described in JP-A-59-129954. Also,
Many of these have a maximum absorption wavelength in solution of 780 nm, which is the oscillation wavelength of a semiconductor laser.
Furthermore, the field of use is limited due to problems such as the fact that it deviates significantly from the standard, and furthermore, it has insufficient light resistance and lacks stability, especially when used as various information materials that use laser light as a light source. was not satisfactory.
本発明は、従来公知のスクアＩＪ ＩＪウム化合物にあ
る上記の問題点を解決しうる新規なスクアリリウム化合
物の提供を目的とする。The present invention aims to provide a novel squarylium compound that can solve the above-mentioned problems of the conventionally known squarylium compounds.
（問題点を解決するための手段）
本発明は、一般式（１）
（式中 Ｒ１、Ｒ２及びＲ３はアルキル基を示しＲ４及
びＲは水素原子、アルキル基、アラルキル基又はアリー
ル基を示し、かつＲ４とＲ５は互いに連結して芳香環又
は環状アルキレン基を形成していてもよく、またＲ６及
びＲ７は水素原子、アルキル基又は置換基（例えばアル
コキシ基、アルコキシアルコキシ基等）を有していても
よいアルコキシ基を示す。）で表わされるスクアリリウ
ム化合物を要旨とするものである。(Means for Solving the Problems) The present invention is based on the general formula (1) (wherein R1, R2, and R3 represent an alkyl group, and R4 and R represent a hydrogen atom, an alkyl group, an aralkyl group, or an aryl group, And R4 and R5 may be linked to each other to form an aromatic ring or a cyclic alkylene group, and R6 and R7 have a hydrogen atom, an alkyl group, or a substituent (for example, an alkoxy group, an alkoxyalkoxy group, etc.). This article focuses on squarylium compounds represented by the following formula (indicates an optional alkoxy group).
本発明の前足一般式（１）で表わされるスクアＩＪ Ｉ
Ｊウム化合物は、一般式ｒＩ）及び一般式（式中、Ｒ１
−Ｒ７は前足一般式ＣＩ）におけると同一の意義を有す
る。）で表わされるアズレン誘導体と、下記構造式：
で表わされる３、４−ジヒドロキシ−３−シクロブテン
−１，２−ジオン、すなわちスクアリック酸とを溶媒中
で反応させることによって、容易に製造することができ
る。Square IJ I represented by the front leg general formula (1) of the present invention
The Jium compound has the general formula rI) and the general formula (wherein R1
-R7 has the same meaning as in the forepaw general formula CI). ) and 3,4-dihydroxy-3-cyclobutene-1,2-dione represented by the following structural formula, that is, squaric acid, in a solvent. can.
前足一般式ＣＩ）で表わされる原料化合物としては、例
えば４，６．８−）ジメチルアズレン。Examples of the raw material compound represented by the general formula CI) include 4,6.8-)dimethylazulene.
６−イツブロビルー４，８−ジメチルアズレン。6-itubrobyl-4,8-dimethylazulene.
６− ｔｅｒｔ−ブチル−４，８−ジメチルアズレン等
が挙げられる。Examples include 6-tert-butyl-4,8-dimethylazulene.
また、前示一般式帽〕で表わされる原料化合物としては
、例えば
アズレン。Further, examples of the raw material compound represented by the general formula shown above include azulene.
１−メチル−２−エチル−５−イソプロピルアズレン。1-Methyl-2-ethyl-5-isopropylazulene.
１−メチル−２−エチル−６−メチルアズレン。1-Methyl-2-ethyl-6-methylazulene.
１−エチル−２−ｎ−プロピル−５−イソプロピルアズ
レン。1-Ethyl-2-n-propyl-5-isopropylazulene.
１−エチル−２−ｎ−７’ロピルー６−イソプロピルア
ズレン。1-Ethyl-2-n-7'ropyru-6-isopropylazulene.
１−ｎ−プロピル−２−ｎ−ブチル−５−イソプロピル
アズレン。1-n-propyl-2-n-butyl-5-isopropylazulene.
１−イソプロピル−２−イソプロピル−５−イソプロピ
ルアズレン。1-isopropyl-2-isopropyl-5-isopropylazulene.
１−ｎ−ブチル−２−ｎ−ペンチル−５−イノプロピル
アズレン。1-n-butyl-2-n-pentyl-5-inopropylazulene.
１−ｎ−ペンチル−２−ｎ−へキシル−６−イソプロピ
ルアズレン。1-n-pentyl-2-n-hexyl-6-isopropylazulene.
１−ｎ−へキシル−２−ｎ−オクチル−６−イソプロピ
ルアズレン。1-n-hexyl-2-n-octyl-6-isopropylazulene.
１−ｎ−デシル−２−ｎ−ウンデシル−５−イソプロピ
ルアズレン。1-n-decyl-2-n-undecyl-5-isopropylazulene.
１．４−ジメチル−７−イソプロピルアズレン。1.4-dimethyl-7-isopropylazulene.
１−ｎ−ドデシル−２−ｎ−）リゾシル−５−イソプロ
ピルアズレン。1-n-dodecyl-2-n-)lysosyl-5-isopropylazulene.
１−メチル−８−メトキシアズレン。1-Methyl-8-methoxyazulene.
１−エチル−８−メトキシアズレン。1-Ethyl-8-methoxyazulene.
１−メチル−５−イソプロピルアズレン。1-Methyl-5-isopropylazulene.
１−エチル−５−イソプロピルアズレン。1-Ethyl-5-isopropylazulene.
１−ｎ−プロピル−５−イノプロピルアズレン。1-n-propyl-5-inopropyl azulene.
１−ブチル−５−イソプロピルアズレン。1-Butyl-5-isopropylazulene.
１−メチル−６−イソプロピルアズレン。1-Methyl-6-isopropylazulene.
１−プロピル−６−イソプロピルアズレン。1-Propyl-6-isopropylazulene.
１−フェニル−５−イソプロピルアズレン。1-phenyl-5-isopropylazulene.
１−ベンジル−５−インプロピルアズレン。1-Benzyl-5-inpropylazulene.
１−ｎ−オクチル−５−イソプロピルアズレン。1-n-octyl-5-isopropylazulene.
１−ｎ−７’シル−５−イソプロピルアズレン。1-n-7'cyl-5-isopropylazulene.
１−ｎ−オクタデシル−５−イソプロピルアズレン。1-n-octadecyl-5-isopropylazulene.
１−メチル−５−メチル−８−メチルアズレン。1-Methyl-5-methyl-8-methylazulene.
１−メチル−６−メチル−８−メチルアズレン。1-Methyl-6-methyl-8-methylazulene.
１−ｎ−ブチル−５−イソプロピル−８−メトキシアズ
レン。1-n-butyl-5-isopropyl-8-methoxyazulene.
１−ｎ−プロピル−５−イソプロピル−８−ｎ−ヘキシ
ルオキシアズレン。1-n-propyl-5-isopropyl-8-n-hexyloxyazulene.
１−エチル−５−イソプロピル−８−ｎ−オクタデシル
オキシアズレン。1-ethyl-5-isopropyl-8-n-octadecyloxyazulene.
１−ｎ−ペンチル−５−イソプロピル−８−エトキシエ
トキシアズレン。1-n-pentyl-5-isopropyl-8-ethoxyethoxyazulene.
１．２−）ジメチレン−５−イソプロピルアズレン。1.2-) Dimethylene-5-isopropylazulene.
１．２−）ジメチレン−６−インプロビルアズレン。1.2-) Dimethylene-6-improvil azulene.
１．２−トリメチレン−５−メチルアズレン。1.2-trimethylene-5-methylazulene.
１．２−）ジメチレン−６−メチルアズレン。1.2-) Dimethylene-6-methylazulene.
１．２−）リメチレンアズレン。1.2-) Rimethylene azulene.
１．２−テトラメチレンアズレン。1.2-tetramethylene azulene.
１．２−テトラメチレン−５−メチルアズレン。1.2-tetramethylene-5-methylazulene.
１．２−テトラメチレン−６−メチルアズレン。1.2-tetramethylene-6-methylazulene.
１．２−テトラメチレン−５−インプロピルアズレン。1.2-tetramethylene-5-inpropylazulene.
１．２−テトラメチレン−６−イソプロピルアズレン。1.2-tetramethylene-6-isopropylazulene.
１．２−ペンタメチレン−５−メチルアズレン。1.2-Pentamethylene-5-methylazulene.
１．２−ペンタメチレン−６−メチルアズレン。1.2-Pentamethylene-6-methylazulene.
１．２−ペンタメチレン−５−イソプロピルアズレン。1.2-Pentamethylene-5-isopropylazulene.
１．２−ペンタメチレン−６−イソプロピルアズレン。1.2-Pentamethylene-6-isopropylazulene.
１．２−へキサメチレン−５−イソプロピルアズレン。1.2-hexamethylene-5-isopropylazulene.
１．２−へキサメチレン−６−イソプロピルアズレン。1.2-hexamethylene-6-isopropylazulene.
１．２−デカメチレン−５−イソプロピルアズレン。1.2-decamethylene-5-isopropylazulene.
１．２−デカメチレン−６−イソプロピルアズレン；（
以下のベンズ（ａ）アズレンのナンバリングはベンズ（
ａ）アズレン。1.2-decamethylene-6-isopropylazulene; (
The numbering of benz(a) azulene below is benz(a)
a) Azulene.
１、２．３．４−テトラヒドロ−３−メチル−ベンズ（
ａ）アズレン。1,2.3.4-tetrahydro-3-methyl-benz (
a) Azulene.
１、２．３．４−テトラヒドロ−３−ｔｅｒｔ−ブチル
−ベンズ（ａ）アズレン。1,2.3.4-Tetrahydro-3-tert-butyl-benz(a) Azulene.
８−インプロピル−ベンズ（ａ）アズレン。8-Inpropyl-benz(a) Azulene.
７−イノプロビルーベンズＣａ）アズレン。7-InoprobyrubenzCa) Azulene.
３−エチル−８゛−イソプロピル−ベンズ（ａ）アズレ
ン。3-ethyl-8'-isopropyl-benz(a) azulene.
３−ｔｅｒｔ−ブチル−８−イソプロピル−ベンズ（ａ
）アズレン。3-tert-butyl-8-isopropyl-benz (a
) Azur Lane.
３−ｎ−オクチル−８−イソプロピル−ベンズ（ａ）ア
ズレン。3-n-octyl-8-isopropyl-benz(a) azulene.
３−ｎ−へブチル−７−メチル−ベンズ〔ａ〕アズレン
。3-n-hebutyl-7-methyl-benz[a]azulene.
３−メトキシ−８−インプロピル−ベンズ（ａ）アズレ
ン。3-methoxy-8-inpropyl-benz(a) azulene.
２−メトキシ−８−インプロピル−ベンズ（ａ）アズレ
ン。2-methoxy-8-inpropyl-benz(a) azulene.
２−ｎ−ブトキシ−８−メチル−ベンズ（ａ）アズレン
。2-n-butoxy-8-methyl-benz(a) azulene.
３−メトキシ−７−イツプロピルーペンズ（ａ）アズレ
ン。3-Methoxy-7-itupropylpenz (a) Azulene.
３−プロモー８−イソプロピル−ベンズ（ａ）アズレン
。3-promo 8-isopropyl-benz(a) azulene.
３−エチル−５−メトキシ−８−インプロピル−ベンズ
（ａ）アズレン。3-ethyl-5-methoxy-8-inpropyl-benz(a) azulene.
３−ｎ−ブチル−５−メトキシ−８−イソプロピル−ベ
ンズ（ａ）アズレン。3-n-Butyl-5-methoxy-8-isopropyl-benz(a) Azulene.
３−ｎ−プロピル−５−ブトキシ−７−インプロピル−
ベンズ（ａ）アズレン。3-n-propyl-5-butoxy-7-inpropyl-
Benz (a) azulene.
５−エトキシエトキシ−８−イソプロピル−ベンズ（ａ
）アズレン。5-ethoxyethoxy-8-isopropyl-benz (a
) Azur Lane.
３−エチル−７−イノプロピルーベンズ（ａ）アズレン
。3-Ethyl-7-inopropyrubenz(a) Azulene.
３−ｎ−プロピル−７−イノプロピルーベンズ〔ａ〕ア
ズレン。3-n-propyl-7-inopropyrubenz[a]azulene.
３−ｎ−プロピル−８−インプロピル−ベンズ（ａ）ア
ズレン。3-n-propyl-8-inpropyl-benz(a) azulene.
３−ｎ−ブチル−８−イソプロピル−ベンズ（ａ）アズ
レン。3-n-Butyl-8-isopropyl-benz(a) Azulene.
３−ｎ−へキシル−７−イノプロピルーベンズ〔ａ〕ア
ズレン。3-n-hexyl-7-inopropyrubenz[a]azulene.
３−ｎ−へブチル−８−メチル−ベンズ（ａ）アズレン
。3-n-hebutyl-8-methyl-benz(a) azulene.
３−ｎ−オクチル−８−メチル−ベンズ（ａ）アズレン
。3-n-octyl-8-methyl-benz(a) azulene.
ａ−ｎ−トｖｙシルー８−メチルーベンズ〔ａ〕アズレ
ン。a-n-tvysil-8-methyl-benz[a] azulene.
２−ｎ−ブトキシ−８−イソプロピル−ベンズ（ａ）ア
ズレン。2-n-Butoxy-8-isopropyl-benz(a) Azulene.
２−ｎ−へブチルオキシ−８−イソプロピル−ベンズ（
ａ）アズレン。2-n-hebutyloxy-8-isopropyl-benz (
a) Azulene.
３−メトキシ−８−イソプロピル−ベンズ（ａ）アズレ
ン。3-methoxy-8-isopropyl-benz(a) azulene.
３−ｔｅｒｔ−ブチル−５−メトキシ−８−イソプロピ
ル−ベンズＣａ）アズレン。3-tert-butyl-5-methoxy-8-isopropyl-benzCa) azulene.
３−エチル−５−ｎ−ブトキン−８−イソプロビル−ベ
ンズ（ａ）アズレン。3-Ethyl-5-n-butquine-8-isopropyl-benz(a) Azulene.
３−ｎ−プロピル−５−ｎ−オクチルオキシ−７−イノ
プロピルーペンズ（ａ）アズレン。3-n-propyl-5-n-octyloxy-7-inopropylpenz (a) Azulene.
５−ｎ−）リゾシルオキシ−８−イソプロピル−ベンズ
〔ａ）アズレン。5-n-) Lysosyloxy-8-isopropyl-benz [a) Azulene.
２−メトキシエトキシ−８−イソプロピル−ベンズ（ａ
）アズレ／。2-methoxyethoxy-8-isopropyl-benz (a
)Azure/.
２−エトキシエトキシエトキシ−８−イソプロピル−ベ
ンズ（ａ）アズレン。2-Ethoxyethoxyethoxy-8-isopropyl-benz(a) Azulene.
５−メトキシエトキシエトキシ−８−インプロピル−ベ
ンズ〔ａ〕アズレン。5-Methoxyethoxyethoxy-8-inpropyl-benz[a]azulene.
３−ｎ−ペンチル−ベンズ（ａ）アズレン。3-n-pentyl-benz(a) azulene.
３−ｎ−ヘプチル−ベンズ（ａ）アズレン。3-n-heptyl-benz(a) azulene.
３−ｎ−プロピル−ベンズ（ａ）アズレン。3-n-propyl-benz(a) azulene.
３−ｔｅｒｔ−ブチル−８−イソプロピル−ベンズ（ａ
）アズレン。3-tert-butyl-8-isopropyl-benz (a
) Azur Lane.
７−イソプロピルーベンズ（ａ）アズレン。7-Isopropyrubenz(a) Azulene.
３−ｎ−へキシル−ベンズ（ａ）アズレン。3-n-hexyl-benz(a) azulene.
３−ｎ−オクチル−８−イソプロピル−ベンズ（ａ）ア
ズレン。3-n-octyl-8-isopropyl-benz(a) azulene.
３−ｎ−ベンチルー７−インプロピル−ベンズ〔ａ〕ア
ズレン。3-n-benzene-7-inpropyl-benz[a]azulene.
３−ｎ−ブチル−７−イソプロビルーベンズ（ａ）アズ
レン等が挙げられる。Examples include 3-n-butyl-7-isoprobyl-benz(a) azulene.
更に、本発明のスクアリリウム化合物の製造反応におい
て用いられる溶媒としては、例えばメタノール、エタノ
ール、１−プロパツール、イソプロパツール、１−ブタ
ノール。Further, examples of the solvent used in the reaction for producing the squarylium compound of the present invention include methanol, ethanol, 1-propanol, isopropanol, and 1-butanol.
２−ブタノール、アミルアルコール、１−ヘキサノール
、シクロヘキサノール、１−ヘプタツール、１−ノナノ
ール等のアルコール類、又は、これらのアルコール類と
ベンゼン、トルエン、キシレン、クロルベンゼン等の芳
香族炭化水素系溶媒との混合溶媒などが挙げられる。ま
た、上記の製造反応における反応温度としては、通常７
０〜１５０℃、好ましくは９０〜１２０℃の温度が用い
られる。Alcohols such as 2-butanol, amyl alcohol, 1-hexanol, cyclohexanol, 1-heptatool, 1-nonanol, or these alcohols and aromatic hydrocarbon solvents such as benzene, toluene, xylene, chlorobenzene, etc. Examples include mixed solvents with In addition, the reaction temperature in the above production reaction is usually 7
Temperatures of 0 to 150°C, preferably 90 to 120°C are used.
（作用）
かくして得られる本発明の新規なスクアリリウム化合物
は、広範な各種の溶媒に可溶である。すなわち、例えば
クロロホルム、ジクロルメタン、ジクロルエタン等の含
ハロゲン炭化水素系溶媒；ジエチル°エーテル、ジオキ
サン、テトラヒドロフラン、ジメトキシエタン等のエー
テル系溶媒；酢酸エチル等のエステル系溶媒；べ／ゼン
、トルエン、キシレン。(Function) The novel squarylium compound of the present invention thus obtained is soluble in a wide variety of solvents. That is, for example, halogen-containing hydrocarbon solvents such as chloroform, dichloromethane, and dichloroethane; ether solvents such as diethyl ether, dioxane, tetrahydrofuran, and dimethoxyethane; ester solvents such as ethyl acetate; benzene, toluene, and xylene.
クロルベンゼン等の芳香族炭化水素系溶媒；アセトアミ
ド、Ｎ−ジメチルアセトアミド。Aromatic hydrocarbon solvents such as chlorobenzene; acetamide, N-dimethylacetamide.
Ｎ−メチルピロリドン等のアミド系溶媒；メタノール、
エタノール、メチルセロソルブ等（７）フルコール系溶
媒；ジメチルスルホキシドなどの溶媒の・いずれにも可
溶である。加えて、これらの溶媒中における極大吸収ス
ペクトルの吸収波長は、半導体レーザーの発振波長領域
である７００〜９０ Ｏｎｍ付近にあり、かつ耐光性が
良好である。Amide solvents such as N-methylpyrrolidone; methanol,
(7) Flucolic solvents such as ethanol and methyl cellosolve; Soluble in any solvent such as dimethyl sulfoxide. In addition, the absorption wavelength of the maximum absorption spectrum in these solvents is around 700 to 90 Onm, which is the oscillation wavelength region of a semiconductor laser, and the light resistance is good.
（実施例）
次に、本発明を実施例により更に具体的に説明するが、
本発明はこれらの実施例に限定されるものではない。(Example) Next, the present invention will be explained in more detail with reference to Examples.
The present invention is not limited to these examples.
実施例１
３．４−ジヒドロキシ−３−シクロブテン−１，２−ジ
オン０．１１ ｆにｎ−ブチルアルコール３０ｍＪを加
え、約１００℃に加熱して溶解した。この溶液に１，４
−ジメチル−７−イソプロビルアズレン０．２０ ｆ、
４，６．８− ）リメチルアズレン０．１７ ｆ及
ヒドルエン２ｏｍＪｔ加え、１０５〜１１０℃で生成す
る水を共沸的に留去しながら約１時間攪拌した。冷却後
、反応溶液をカラムクロマトグラフィーにより精−製し
て、下記構造式：
で示される化合物ｏ、 ｏ ｓ ｔを得た。本化合物は
２３２〜２３３℃の融点を示し、そのクロロホルム溶液
中での吸収スペクトルの極大吸収波長は７４４ ｎｍで
あった。Example 1 30 mJ of n-butyl alcohol was added to 0.11 f of 3.4-dihydroxy-3-cyclobutene-1,2-dione and dissolved by heating to about 100°C. 1,4 in this solution
-dimethyl-7-isopropylazulene 0.20 f,
0.17 f of 4,6.8-)limethylazulene and 2 omJt of hydrene were added, and the mixture was stirred for about 1 hour while water produced at 105 to 110°C was azeotropically distilled off. After cooling, the reaction solution was purified by column chromatography to obtain compounds o and ost represented by the following structural formulas. This compound exhibited a melting point of 232 to 233°C, and the maximum absorption wavelength of its absorption spectrum in a chloroform solution was 744 nm.
実施例２
実施例１の方法に準じて合成した本発明のスクアリリウ
ム化合物の他の例（３２種）につき、それぞれの構造式
及びクロロホルム溶液中での極大吸収波長λｍａｘ（ｎ
ｍ）をまとめて下記第１表の１〜３に表示する。Example 2 Other examples (32 types) of squarylium compounds of the present invention synthesized according to the method of Example 1, their respective structural formulas and maximum absorption wavelength λmax(n
m) are collectively shown in 1 to 3 of Table 1 below.
（発明の効果）
以上の結果から明らかなように、本発明の新規なスクア
ＩＪ １７ウム化合物は、広範な各種溶媒のいずれにも
可溶性を示すばかりでなく、これらの溶媒中における極
大吸収波長味、半導体レーザーの発振波長領域である７
００〜９００ ｎｍの付近にあシ、シかも耐光性が良好
である、という工業的価値ある顕著な効果を奏するもの
である。したがって、レーザー光を利用する各種情報材
料、例えばレーザー書き込み液晶表示用レーザー光吸収
材料、レーザーを光源とした電子写真プリンターの電子
写真感光材料、レーザーによる書き込みと読み出しが可
能な晃ディスク用記録材料、あるいは赤外線カットフィ
ルターなどの分野で、その有用性が期待される。(Effects of the Invention) As is clear from the above results, the novel SQUA IJ 17um compound of the present invention not only exhibits solubility in a wide range of various solvents, but also exhibits a maximum absorption wavelength in these solvents. , which is the oscillation wavelength region of the semiconductor laser 7
It has excellent light resistance in the vicinity of 00 to 900 nm, which is a remarkable effect of industrial value. Therefore, various information materials that utilize laser light, such as laser-written laser light-absorbing materials for liquid crystal displays, electrophotographic photosensitive materials for electrophotographic printers using lasers as light sources, recording materials for optical discs that can be written and read by laser, It is also expected to be useful in fields such as infrared cut filters.
Claims (1)
、Ｒ＾４及びＲ＾５は水素原子、アルキル基、アラルキ
ル基又はアリール基を示し、かつＲ＾４とＲ＾５は互い
に連結して芳香環又は環状アルキレン基を形成していて
もよく、またＲ＾６及びＲ＾７は水素原子、アルキル基
又は置換基を有していてもよいアルコキシ基を示す。）
で表わされるスクアリリウム化合物。(1) General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼... [I] (In the formula, R^1, R^2 and R^3 represent an alkyl group, R^4 and R ^5 represents a hydrogen atom, an alkyl group, an aralkyl group, or an aryl group, and R^4 and R^5 may be linked to each other to form an aromatic ring or a cyclic alkylene group, and R^6 and R ^7 represents a hydrogen atom, an alkyl group, or an alkoxy group that may have a substituent.)
A squarylium compound represented by
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10158085A JPS61260038A (en) | 1985-05-15 | 1985-05-15 | Squarylium compound |
| DE8585309198T DE3583013D1 (en) | 1984-12-19 | 1985-12-17 | SQUARILIUM COMPOUNDS AND LIQUID CRYSTAL COMPOSITIONS CONTAINING THEM. |
| EP85309198A EP0187015B1 (en) | 1984-12-19 | 1985-12-17 | Squarilium compound and liquid crystal composition containing the same |
| US07/605,215 US5037575A (en) | 1984-12-19 | 1990-10-29 | Squarilium compound and liquid crystal composition containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10158085A JPS61260038A (en) | 1985-05-15 | 1985-05-15 | Squarylium compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS61260038A true JPS61260038A (en) | 1986-11-18 |
Family
ID=14304327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10158085A Pending JPS61260038A (en) | 1984-12-19 | 1985-05-15 | Squarylium compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61260038A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63235370A (en) * | 1987-03-25 | 1988-09-30 | Nippon Kayaku Co Ltd | Light-condensing resin sheet |
| JPH0326593A (en) * | 1989-06-16 | 1991-02-05 | Eastman Kodak Co | Infrared ray absorbing squaleirylium dye for dye donating element which is used for laser induction dye heat transfer |
| US5085909A (en) * | 1988-04-28 | 1992-02-04 | Ricoh Company, Ltd. | Squarylium compounds and optical information recording medium using the same |
| US5275917A (en) * | 1991-07-09 | 1994-01-04 | Brother Kogyo Kabushiki Kaisha | Photocurable composition |
| US5470683A (en) * | 1993-07-28 | 1995-11-28 | Brother Kogyo Kabushiki Kaisha | Photosensitive microcapsule toner |
| US6171759B1 (en) | 1992-05-14 | 2001-01-09 | Brother Kogyo Kabushiki Kaisha | Photocurable composition |
-
1985
- 1985-05-15 JP JP10158085A patent/JPS61260038A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63235370A (en) * | 1987-03-25 | 1988-09-30 | Nippon Kayaku Co Ltd | Light-condensing resin sheet |
| US5085909A (en) * | 1988-04-28 | 1992-02-04 | Ricoh Company, Ltd. | Squarylium compounds and optical information recording medium using the same |
| JPH0326593A (en) * | 1989-06-16 | 1991-02-05 | Eastman Kodak Co | Infrared ray absorbing squaleirylium dye for dye donating element which is used for laser induction dye heat transfer |
| JPH0512156B2 (en) * | 1989-06-16 | 1993-02-17 | Eastman Kodak Co | |
| US5275917A (en) * | 1991-07-09 | 1994-01-04 | Brother Kogyo Kabushiki Kaisha | Photocurable composition |
| US6171759B1 (en) | 1992-05-14 | 2001-01-09 | Brother Kogyo Kabushiki Kaisha | Photocurable composition |
| US5470683A (en) * | 1993-07-28 | 1995-11-28 | Brother Kogyo Kabushiki Kaisha | Photosensitive microcapsule toner |
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