JPS60228448A - Squarylium compound - Google Patents
Squarylium compoundInfo
- Publication number
- JPS60228448A JPS60228448A JP59085508A JP8550884A JPS60228448A JP S60228448 A JPS60228448 A JP S60228448A JP 59085508 A JP59085508 A JP 59085508A JP 8550884 A JP8550884 A JP 8550884A JP S60228448 A JPS60228448 A JP S60228448A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- alkyl
- groups
- compound shown
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 20
- -1 tetrahydrofurfuryl Chemical group 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 8
- 238000010521 absorption reaction Methods 0.000 abstract description 7
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 2
- 229910052736 halogen Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 101000650578 Salmonella phage P22 Regulatory protein C3 Proteins 0.000 description 1
- 101001040920 Triticum aestivum Alpha-amylase inhibitor 0.28 Proteins 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- QPWNLIBZQKTIJR-UHFFFAOYSA-N n-[3-(diethylamino)-2-methoxyphenyl]acetamide Chemical compound CCN(CC)C1=CC=CC(NC(C)=O)=C1OC QPWNLIBZQKTIJR-UHFFFAOYSA-N 0.000 description 1
- FPUKYOSOAAPHTN-UHFFFAOYSA-N n-[3-(diethylamino)phenyl]acetamide Chemical compound CCN(CC)C1=CC=CC(NC(C)=O)=C1 FPUKYOSOAAPHTN-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 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
Landscapes
- Light Receiving Elements (AREA)
- Photoreceptors In Electrophotography (AREA)
- Furan Compounds (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、新規なスクアリリウム化合物に関するもので
ある。詳しくは１ｇＱ Ｑ ｎｌｎ付近までの領域にお
いて吸収を有しており、レーザー書き込み液晶表示やレ
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
材料やレーザーにより書き込みと読み出しが可能な元デ
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を期待される新規なスクアリリウム
化合物に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a novel squarylium compound. Specifically, it has absorption in the region up to around 1gQQnln, and is used in laser-written liquid crystal displays and electrophotographic photosensitive materials for electrophotographic printers using lasers as light sources, and recording materials for original discs that can be written and read by lasers. The present invention relates to a novel squarylium compound that is expected to be useful in fields such as infrared cut filters.
スクアＩＪ ＩＪウム化合物が光導電性を示し１例えば
、電子写真用感光体の電荷発生剤として使用されている
ことは知られている（４ＩｌＦ開昭ダ９−）θ３よ３６
）。It is known that the SQUA compound exhibits photoconductivity and is used, for example, as a charge generating agent in electrophotographic photoreceptors.
).
しかし、従来のスクアリリウム化合物は、一般に、溶液
中ではせいぜいｂｓｏｒｘｍ付近までの吸収を有するに
すぎず、近年、その応用検討が活発になっているレーザ
ー元ケ光源とする各糧情報材料として使用するには必ず
しも十分とはいえず改善が望まれていた。However, conventional squarylium compounds generally have an absorption of around bsorxm at most in solution, and in recent years, their application has been actively studied for use as a light source for laser sources. were not necessarily sufficient and improvements were desired.
本発明者らは、かかる点に留意し鋭意検討した結果、特
定のスクアＩＪ ＩＪウム化合物が所期の目的を達成し
得ることを知得し１本発明を完成するに到った。The inventors of the present invention, as a result of careful studies with these points in mind, have found that a specific SQUA IJ compound can achieve the intended purpose, and have completed the present invention.
即ち１本発明の要旨は、一般式ｍ
〔式中、Ｒ１およびＲ２は置換基を有していてもよいア
ルキル基、または、テトラヒドロフルフリル基な示し、
また Ｒ１とＲ２は互いに連結して含窒素環を形成して
いてもよい。Ｘは置換基を有していてもよいアルキル基
もしくはアルコキシ基・または・パ°ゲ７原子を示し・
１は」−Ｒ３または一〇〇、−Ｒ４（Ｒ３およびＲ４は
置換基を有していてもよいアルキル基もしくはフェニル
基、または、水素原子ケ示す。）を示す。〕で表わされ
るスクアリリウム化合物に存する。That is, 1 gist of the present invention is the general formula m [wherein R1 and R2 are an alkyl group which may have a substituent or a tetrahydrofurfuryl group,
Further, R1 and R2 may be connected to each other to form a nitrogen-containing ring. X represents an alkyl group or alkoxy group which may have a substituent, or a Page 7 atom.
1 represents -R3 or 100, -R4 (R3 and R4 represent an optionally substituted alkyl group or phenyl group, or a hydrogen atom). ] It exists in the squarylium compound represented by
本発明を説明するに１本発明のスクアリリウム化合物は
前記一般式［１１で表わされるものである。To explain the present invention, the squarylium compound of the present invention is represented by the general formula [11].
式中 Ｂｌおよび斧は置換基を有していてもよいメチル
基、エチル基、プロピル基、ブチル基、ペンチル基、ヘ
キシル基、ヘプチル基等のアルキル基、または、テトラ
ヒドロフルフリル基ン示す０
置換基としては、ヒドロキシ基；シアノ基；フッ素原子
、塩素原子、臭素原子等のハロゲン原子；メトキシ基、
プロポキシ基、ブトキシ基、オクトキシ基等のアルコキ
シ基；メトキシエトキシ基、ブトキシエトキシ基、エト
キシメトキシ基、ヒドロキシブトキシ基等のアルコキシ
アルコキシ基ニジクロヘキシル基、プロピルシクロヘキ
シル基、ブチルシクロヘキシル基、ペンチルシクロヘキ
シル基等のシクロアルキル基；アセチルアミノ基、ペン
タノイルアミノ基、オクタノイルアミノ基等のアシルア
ミノ基；アセチルオキシ基、ゾロパノイルオキシ基、ヘ
キサノイルオキシ基等のアシルオキシ基：フェニル基、
プロピルフェニル基、ブチルフェニル基。In the formula, Bl and ax represent an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and a heptyl group, which may have a substituent, or a tetrahydrofurfuryl group. As a group, hydroxy group; cyano group; halogen atom such as fluorine atom, chlorine atom, bromine atom; methoxy group,
Alkoxy groups such as propoxy, butoxy, octoxy groups; alkoxyalkoxy groups such as methoxyethoxy, butoxyethoxy, ethoxymethoxy, hydroxybutoxy, dichlorohexyl, propylcyclohexyl, butylcyclohexyl, pentylcyclohexyl, etc. cycloalkyl group; acylamino group such as acetylamino group, pentanoylamino group, octanoylamino group; acyloxy group such as acetyloxy group, zolopanoyloxy group, hexanoyloxy group: phenyl group,
Propylphenyl group, butylphenyl group.
ヘプチルフェニル基、ブトキシフェニル基、ペンチルオ
キシフェニル基、ヘキシルオキシフェニル基、ヘプチル
オキシフェニル基、ブトキシメチルフェニル基等のアリ
ール基；フェノキシ基、ブチルフェノキシ基、ヘキシル
フェノキシ基、ブトキシフェノキシ基、エトキシメチル
フェノキシ基等のアリールオキシ基；プロポキシカルボ
ニル基、ブトキシカルボニル基、ヘプチルオキシカルボ
ニル基等のアルコキシカルボニル基等が挙げられる。Aryl groups such as heptyl phenyl group, butoxyphenyl group, pentyloxyphenyl group, hexyloxyphenyl group, heptyloxyphenyl group, butoxymethylphenyl group; phenoxy group, butylphenoxy group, hexylphenoxy group, butoxyphenoxy group, ethoxymethylphenoxy Aryloxy groups such as groups; alkoxycarbonyl groups such as propoxycarbonyl group, butoxycarbonyl group, heptyloxycarbonyl group, and the like.
また Ｒ１と頂は互いに連結してモルホリノ基。Also, R1 and the apex are connected to each other to form a morpholino group.
ヒヘラジノ基等の含窒素環を形成していてもよい。A nitrogen-containing ring such as a hyherazino group may be formed.
Ｘは、置換基を有していてもよいメチル基。X is a methyl group which may have a substituent.
エチル基、プロピル基、ブチル基、ペンチル基。Ethyl group, propyl group, butyl group, pentyl group.
ヘキシル基、ヘプチル基等のアルキル基もしくはメトキ
シ基、エトキシ基、プロポ中シ基、ブトキシ基等のアル
コキシ基、または、フッ素原子、臭素原子、塩素原子等
のハロゲン原子を示す。It represents an alkyl group such as a hexyl group or a heptyl group, an alkoxy group such as a methoxy group, an ethoxy group, a propoxy group, or a butoxy group, or a halogen atom such as a fluorine atom, a bromine atom, or a chlorine atom.
ここでアルキル基の置換基としては、メトキシ基、エト
キシ基、ブトキシ基、ヘキシルオキシ基等のアルコキシ
基：Ｎ、Ｎ−ジメチルアミノ基、Ｎ−メチル−Ｎ−エチ
ルアミノ基、Ｎ−メチル−Ｎ−ブチルアミノ基等のアル
キルアミノ基等が挙げられる。また、アルコキシ基の置
換基としては、メトキシ基、エトキシ基、ブトキシ基等
のアルコキシ基；メトキシエトキシ基。Here, as substituents for the alkyl group, alkoxy groups such as methoxy group, ethoxy group, butoxy group, hexyloxy group: N, N-dimethylamino group, N-methyl-N-ethylamino group, N-methyl-N Examples include alkylamino groups such as -butylamino group. Further, as a substituent for an alkoxy group, an alkoxy group such as a methoxy group, an ethoxy group, a butoxy group; a methoxyethoxy group;
エトキシブトキシ基、ブトキシエトキシ基等のアルコキ
シアルコキシ基等が挙げられる。Examples include alkoxyalkoxy groups such as ethoxybutoxy group and butoxyethoxy group.
Ｙは、Ａ−Ｒ３１りｋｔ−８０ｚＲ４Ｙ示ス。Ｒｓオヨ
ヒＲ４は、置換基を有していてもよいメチル基、エチル
基、プロピル基、ブチル基、ヘキシル基。Y indicates A-R31kt-80zR4Y. Rs Oyohi R4 is a methyl group, ethyl group, propyl group, butyl group, or hexyl group that may have a substituent.
オクチル基等のアルキル基もしくはフェニル基。Alkyl groups such as octyl groups or phenyl groups.
または、水素原子乞示す。Or ask for a hydrogen atom.
ここでアルキル基の置換基としては、メトキシ基、エト
キシ基、ブトキシ基等のアルコキシ基；フッ素原子、臭
素原子、塩素原子等の７・ロゲン原子が挙げられる、ま
た、フェニル基の置換基としては、メチル基、エチル基
、プロピル基、ブチル基等のアルキル基；メトキシ基、
工゛トキシ基、ブトキシ基等のアルコキシ基等が挙げら
れる。Examples of substituents for the alkyl group include alkoxy groups such as methoxy, ethoxy, and butoxy groups; and 7-rogen atoms such as fluorine, bromine, and chlorine atoms. , alkyl groups such as methyl group, ethyl group, propyl group, butyl group; methoxy group,
Examples include alkoxy groups such as methoxy groups and butoxy groups.
前記一般式［Ｉ）で示される化合物は例えば下記構造式
ＣＩＩＩ
（式中、 Ｒ１，Ｒ２，ＸオｊびＹ ハ式［：Ｉｌｃお
けると同一の意義を有する。）で示される化合物と３、
タージヒドロキシ−３−シクロブテン−１，コージオン
とｔ溶媒中で反応させることによって製造される。The compound represented by the general formula [I] is, for example, a compound represented by the following structural formula CIII (wherein, R1, R2,
It is produced by reacting terdihydroxy-3-cyclobutene-1 with cordion in a t-solvent.
本発明のスクアリリウム化合物は、後述の実施例に示す
ようにｂｏｏからざ０θｎｍ付近に極大吸収を有する。The squarylium compound of the present invention has maximum absorption near 0θnm from boo, as shown in the Examples below.
従って、レーザー光を光源とする各種情報材料、例えば
、レーザー書き込み液晶表示やレーザー！光源とした電
子写真プリンターの電子写真感光材料やレーザーにより
書き込みと読み出しが可能な光デイ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を
期待される。Therefore, various information materials that use laser light as a light source, such as laser-written liquid crystal displays and laser! It is expected to be useful in fields such as electrophotographic photosensitive materials for electrophotographic printers that use light sources, recording materials for optical disks that can be written and read by laser, and infrared cut filters.
次に本発明を実施例によってさらに具体的に説明する。 Next, the present invention will be explained in more detail with reference to Examples.
実施例１
３、ｌ−ジヒドロキシ−３−シクロブテン−７，コージ
オン０．．ｊｇｊｉＫｎ−ブチルアルコールｔｒｍｌｚ
加え７００℃に加熱して溶解する。この溶液にコーメト
キシー３−アセチルアミノ−Ｎ、Ｎ−ジエチルアニリン
ｔ、ｂｓｇ）−ｏ−ジクロロベンゼンコＡ；ｒｄｙｇ加
え還流下、生ずる水乞除きながら３０分反応させた。室
温に冷却様反応液なカラムクロマトにより精製して下記
構造式で示される化合物を得た。本化合物はコＯａ、Ｏ
〜２０４１．１℃の融点を示しクロロホルム溶液中での
可視部吸収スペクトルの極大吸収波長は７ダｊｎｌｆｌ
であった。Example 1 3, l-dihydroxy-3-cyclobutene-7, cordion 0. ．． jgjiKn-butyl alcohol trmlz
Add and heat to 700°C to dissolve. Comethoxy 3-acetylamino-N,N-diethylaniline t, bsg)-o-dichlorobenzene A;rdyg was added to this solution and allowed to react for 30 minutes under reflux while removing the resulting water. The reaction solution was cooled to room temperature and purified by column chromatography to obtain a compound represented by the following structural formula. This compound is co-Oa, O
It has a melting point of ~2041.1°C and the maximum absorption wavelength of the visible absorption spectrum in a chloroform solution is 7 dajnlfl.
Met.
実施例コ
実施例１において使用した２−メトキシ−３−アセチル
アミノ−Ｎ、Ｎ−ジエチルアニリンのかわりに、λ−メ
トキシー３−ホルムアミノーＮ、Ｎ−ジエチルアニリノ
１．１１．
と以外は実施例／と同様の操作方法により下記構造式
で示される化合物を得た。本化合物はコθ０．０〜コＯ
Ｏ．Ｓ℃の融点を示し、クロロホルム溶液中での可視部
吸収スペクトルの極大吸収波長は。Example Instead of 2-methoxy-3-acetylamino-N,N-diethylaniline used in Example 1, λ-methoxy-3-formamino-N,N-diethylanilino 1.11. A compound represented by the following structural formula was obtained in the same manner as in Example except for the above. This compound is 0.0 to 0
O. It shows the melting point of S°C and the maximum absorption wavelength of the visible absorption spectrum in chloroform solution.
りＩＩＯｎｍであった。It was IIOnm.
実施例３
実施例１及び実施例−に準じて合成した本発明のスクア
リリウム化合物の例を第１表にクロロホルム溶液中での
極大吸収波長とともに記す。Example 3 Examples of squarylium compounds of the present invention synthesized according to Examples 1 and 2 are shown in Table 1 along with their maximum absorption wavelengths in chloroform solutions.
第１表 １− − 第１頁の続きTable 1 1- − Continuation of page 1
Claims (1)
ルキル基、または、テトラヒドロフルフリル基を示し、
また Ｒ１とＢｌｚは互いに連結して含窒素環音形成し
ていてもよい。Ｘは置換基を有していても占いアルキル
基もしくはアルコキシ基、または、ハロゲン原子を示し
。 Ｙは−３−Ｒ３′ｆ−たは−８０，−Ｒ４け゛および１
゛シ１置換基を有していてもよいアルキル基もしくはフ
ェニル基、または、水１Ｌ原子ｌ示す。）を示す。〕で
表わされるスクアリリウム化合物。(1) General formula [■] [In the formula, R1 and R represent an alkyl group that may have a substituent or a tetrahydrofurfuryl group,
Further, R1 and Blz may be linked to each other to form a nitrogen-containing ring. Even if X has a substituent, it represents an alkyl group, an alkoxy group, or a halogen atom. Y is -3-R3'f- or -80, -R4 digits and 1
゛1 indicates an alkyl group or phenyl group which may have a substituent, or 1 L atom of water. ) is shown. ] A squarylium compound represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59085508A JPS60228448A (en) | 1984-04-27 | 1984-04-27 | Squarylium compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59085508A JPS60228448A (en) | 1984-04-27 | 1984-04-27 | Squarylium compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS60228448A true JPS60228448A (en) | 1985-11-13 |
Family
ID=13860870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59085508A Pending JPS60228448A (en) | 1984-04-27 | 1984-04-27 | Squarylium compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60228448A (en) |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5543086A (en) * | 1987-08-12 | 1996-08-06 | Gentex Corporation | Squarylium dyestuffs and compostions containing same |
| US6171759B1 (en) | 1992-05-14 | 2001-01-09 | Brother Kogyo Kabushiki Kaisha | Photocurable composition |
| WO2002020671A1 (en) * | 2000-09-04 | 2002-03-14 | Mitsubishi Chemical Corporation | Diphenylsquarylium compound and display filter containing the same |
| WO2006025887A3 (en) * | 2004-05-21 | 2006-08-10 | Becton Dickinson Co | Long wavelength thiol-reactive fluorophores |
| JP2014059550A (en) * | 2012-08-23 | 2014-04-03 | Asahi Glass Co Ltd | Near-infrared cut filter |
| JP2014066918A (en) * | 2012-09-26 | 2014-04-17 | Asahi Glass Co Ltd | Image capturing lens and image capturing device |
| WO2015056734A1 (en) * | 2013-10-17 | 2015-04-23 | Jsr株式会社 | Optical filter, solid-state image pickup device, and camera module |
| JP2015086378A (en) * | 2013-09-26 | 2015-05-07 | 住友化学株式会社 | Compound |
| US9575213B2 (en) | 2011-10-14 | 2017-02-21 | Jsr Corporation | Optical filter, and solid-state image pickup device and camera module using the optical filter |
| US9746595B2 (en) | 2012-06-25 | 2017-08-29 | Jsr Corporation | Solid-state image capture element optical filter and application thereof |
| US9966402B2 (en) | 2014-12-04 | 2018-05-08 | Jsr Corporation | Solid-state imaging device |
| CN108727859A (en) * | 2017-05-23 | 2018-11-02 | 福州大学 | Squaraine dye and its colorimetric fluorescence double-bang firecracker answer copper ion probe prepare application |
| US10473836B2 (en) | 2015-07-28 | 2019-11-12 | Jsr Corporation | Optical filter and ambient light sensor including optical filter |
| US10854661B2 (en) | 2015-01-21 | 2020-12-01 | Jsr Corporation | Solid-state imaging device, infrared-absorbing composition, and flattened-film-forming curable composition |
| KR20210013239A (en) * | 2013-09-26 | 2021-02-03 | 동우 화인켐 주식회사 | Colored curable resin composition |
| US11163098B2 (en) | 2016-06-08 | 2021-11-02 | Jsr Corporation | Optical filter and optical sensor device |
-
1984
- 1984-04-27 JP JP59085508A patent/JPS60228448A/en active Pending
Cited By (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5543086A (en) * | 1987-08-12 | 1996-08-06 | Gentex Corporation | Squarylium dyestuffs and compostions containing same |
| 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 |
| WO2002020671A1 (en) * | 2000-09-04 | 2002-03-14 | Mitsubishi Chemical Corporation | Diphenylsquarylium compound and display filter containing the same |
| US6836383B1 (en) | 2000-09-04 | 2004-12-28 | Mitsubishi Chemical Corporation | Diphenylsquarylium compound and filter for display containing the same |
| WO2006025887A3 (en) * | 2004-05-21 | 2006-08-10 | Becton Dickinson Co | Long wavelength thiol-reactive fluorophores |
| US7563891B2 (en) | 2004-05-21 | 2009-07-21 | Becton, Dickinson & Company | Long wavelength thiol-reactive fluorophores |
| US7767821B2 (en) | 2004-05-21 | 2010-08-03 | Becton, Dickinson & Company | Long wavelength thiol-reactive fluorophores |
| US8071794B2 (en) | 2004-05-21 | 2011-12-06 | Becton, Dickinson And Company | Long wavelength thiol-reactive fluorophores |
| US8129525B2 (en) | 2004-05-21 | 2012-03-06 | Becton Dickinson And Company | Long wavelength thiol-reactive fluorophores |
| US9791606B2 (en) | 2011-10-14 | 2017-10-17 | Jsr Corporation | Optical filter, and solid-state image pickup device and camera module using the optical filter |
| US9791596B2 (en) | 2011-10-14 | 2017-10-17 | Jsr Corporation | Optical filter, and solid-state image pickup device and camera module using the optical filter |
| US9575213B2 (en) | 2011-10-14 | 2017-02-21 | Jsr Corporation | Optical filter, and solid-state image pickup device and camera module using the optical filter |
| US9746595B2 (en) | 2012-06-25 | 2017-08-29 | Jsr Corporation | Solid-state image capture element optical filter and application thereof |
| JP2014059550A (en) * | 2012-08-23 | 2014-04-03 | Asahi Glass Co Ltd | Near-infrared cut filter |
| JP2014066918A (en) * | 2012-09-26 | 2014-04-17 | Asahi Glass Co Ltd | Image capturing lens and image capturing device |
| KR20210013239A (en) * | 2013-09-26 | 2021-02-03 | 동우 화인켐 주식회사 | Colored curable resin composition |
| JP2015086378A (en) * | 2013-09-26 | 2015-05-07 | 住友化学株式会社 | Compound |
| JP5884953B2 (en) * | 2013-10-17 | 2016-03-15 | Jsr株式会社 | Optical filter, solid-state imaging device, and camera module |
| WO2015056734A1 (en) * | 2013-10-17 | 2015-04-23 | Jsr株式会社 | Optical filter, solid-state image pickup device, and camera module |
| JPWO2015056734A1 (en) * | 2013-10-17 | 2017-03-09 | Jsr株式会社 | Optical filter, solid-state imaging device, and camera module |
| US9606275B2 (en) | 2013-10-17 | 2017-03-28 | Jsr Corporation | Optical filter, solid-state image pickup device and camera module |
| US9966402B2 (en) | 2014-12-04 | 2018-05-08 | Jsr Corporation | Solid-state imaging device |
| US10854661B2 (en) | 2015-01-21 | 2020-12-01 | Jsr Corporation | Solid-state imaging device, infrared-absorbing composition, and flattened-film-forming curable composition |
| US10473836B2 (en) | 2015-07-28 | 2019-11-12 | Jsr Corporation | Optical filter and ambient light sensor including optical filter |
| US11226442B2 (en) | 2015-07-28 | 2022-01-18 | Jsr Corporation | Optical filter and ambient light sensor including optical filter |
| US11163098B2 (en) | 2016-06-08 | 2021-11-02 | Jsr Corporation | Optical filter and optical sensor device |
| CN108727859B (en) * | 2017-05-23 | 2019-12-17 | 福州大学 | squaric acid dye and application thereof in preparation of colorimetric fluorescence dual-response copper ion probe |
| CN108727859A (en) * | 2017-05-23 | 2018-11-02 | 福州大学 | Squaraine dye and its colorimetric fluorescence double-bang firecracker answer copper ion probe prepare application |
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