JPH0244475B2 - FUTAROSHIANIN KAGOBUTSU - Google Patents
FUTAROSHIANIN KAGOBUTSUInfo
- Publication number
- JPH0244475B2 JPH0244475B2 JP28119184A JP28119184A JPH0244475B2 JP H0244475 B2 JPH0244475 B2 JP H0244475B2 JP 28119184 A JP28119184 A JP 28119184A JP 28119184 A JP28119184 A JP 28119184A JP H0244475 B2 JPH0244475 B2 JP H0244475B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- phthalocyanine
- infrared
- compound
- yield
- 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.)
- Expired - Lifetime
Links
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 9
- -1 phthalocyanine compound Chemical class 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229910052733 gallium Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052738 indium Inorganic materials 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- RFCQDOVPMUSZMN-UHFFFAOYSA-N 2-Naphthalenethiol Chemical compound C1=CC=CC2=CC(S)=CC=C21 RFCQDOVPMUSZMN-UHFFFAOYSA-N 0.000 description 1
- 229910021617 Indium monochloride Inorganic materials 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical group ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 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 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- APHGZSBLRQFRCA-UHFFFAOYSA-M indium(1+);chloride Chemical compound [In]Cl APHGZSBLRQFRCA-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000005671 trienes Chemical class 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
【発明の詳細な説明】
発明の背景
技術分野
本発明は、フタロシアニン化合物、特に近赤外
および赤外域に吸収をもつフタロシアニン化合物
に関する。
先行技術とその問題点
フタロシアニン化合物は、光、熱、湿度等、い
ずれに対しても安定であり、堅牢性に優れてい
る。特に、金属フタロシアニンは、その高い安定
性と強い色調から各種の染料あるいは顔料として
広く用いられているほか、大きなπ電子共役系の
中に金属イオンが存在するため、電導、光電導、
エネルギー変換、電極、触媒等の材料として、ま
た高分子とブレンドすることにより高度の機能を
有するフイルムや薄膜等の高分子材料などとして
注目され、種々研究が行われている。
これらのフタロシアニン化合物の用途の１つに
光の吸収剤としての役割が挙げられる。
しかし、吸収剤として用いた場合、近赤外およ
び赤外域に吸収がなく、近赤外および赤外域に吸
収をもつたフタロシアニン化合物が要望されてい
る。
発明の目的
本発明の目的は、近赤外および赤外域に吸収を
もつフタロシアニン化合物を提供するとにある。
発明の開示
このような目的は、下記の本発明によつて達成
される。
すなわち、本発明は
式
MX−Pc（−SR）o（Ｙ）16-o
｛式中、ＭはAl、GaまたはInを表わす。
Ｘは、ハロゲン原子を表わす。
PCは、フタロシアニン核を表わす。
Ｒは、炭素原子数１〜２０のアルキル基または
炭表原子数６〜２４のアリール基、アルキルアリ
ール基、アルコキシアリール基もしくはハロゲン
置換アリール基を表わす。
Ｙは、水素原子またはハロゲン原子を表わす。
ｎは、５〜１６の正の整教を表わす。｝
で示されることを特徴とするフタロシニアン化合
物。
発明の具体的構成
以下、本発明の具体的構成について詳細に説明
する。
本発明のフタロシアニン化合物は、下記式
（）で示されるものである。
式
MX−PC（−SR）ｎ（Ｙ）16-n（）
上記式（）において、Ｍは、Ａ金属原子の
うちAl，Ga，Inである。
Ｘはハロゲン原子、例えばＦ，Cl，Br，Ｉ
等；であり、なかでもCl，Brが好ましい。
Pcは下記式（）で表わされるフタロシアニ
ン核である。
式
上記式（）で、−SRもしくはＹが置換する位
置は１〜16のいずれかである。
Ｒは、炭素数１〜20の非置換のアルキル基、例
えば、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、ドデシル基等；
それぞれ、炭素数６〜24の
非置換のアリール基、例えばフエニル基、ナフ
チル基等；
アルキルアリール基、例えばトリル基、キシリ
基等；
アルコキシアリール基、例えばメトキシフエニ
ル基、BACKGROUND OF THE INVENTION Technical Field The present invention relates to phthalocyanine compounds, particularly phthalocyanine compounds having absorption in the near-infrared and infrared regions. Prior art and its problems Phthalocyanine compounds are stable against light, heat, humidity, etc. and have excellent robustness. In particular, metal phthalocyanines are widely used as various dyes and pigments due to their high stability and strong color tone.In addition, metal phthalocyanines are widely used as various dyes and pigments due to their high stability and strong color tone.
It has attracted attention as a material for energy conversion, electrodes, catalysts, etc., and as a polymer material for films and thin films that have advanced functions when blended with polymers, and various studies are being conducted on it. One of the uses of these phthalocyanine compounds is as a light absorber. However, when used as an absorbent, there is a demand for phthalocyanine compounds that do not absorb in the near-infrared and infrared regions but have absorption in the near-infrared and infrared regions. OBJECT OF THE INVENTION An object of the present invention is to provide a phthalocyanine compound having absorption in the near-infrared and infrared regions. DISCLOSURE OF THE INVENTION These objects are achieved by the invention described below. That is, the present invention has the following formula: MX-Pc(-SR) o (Y) 16-o {wherein M represents Al, Ga, or In. X represents a halogen atom. PC stands for phthalocyanine nucleus. R represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 24 carbon atoms, an alkylaryl group, an alkoxyaryl group, or a halogen-substituted aryl group. Y represents a hydrogen atom or a halogen atom. n represents a positive order of 5 to 16. } A phthalocyanine compound characterized by the following. Specific Configuration of the Invention The specific configuration of the present invention will be described in detail below. The phthalocyanine compound of the present invention is represented by the following formula (). Formula MX-PC(-SR)n(Y) 16- n() In the above formula (), M is Al, Ga, or In among A metal atoms. X is a halogen atom, such as F, Cl, Br, I
etc.; among them, Cl and Br are preferred. Pc is a phthalocyanine nucleus represented by the following formula (). formula In the above formula (), the position substituted by -SR or Y is any one of 1 to 16. R is an unsubstituted alkyl group having 1 to 20 carbon atoms, such as a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, dodecyl group; Aryl groups, such as phenyl group, naphthyl group, etc.; Alkylaryl groups, such as tolyl group, xyly group, etc.; Alkoxyaryl groups, such as methoxyphenyl group,
【式】等；
ハロゲン置換アリール基、例えば塩化フエニル
基等；
である。
Ｙは、水素原子；
ハロゲン原子、例えば、Cl、Br、Ｉ、Ｆ等；
であり、なかでも、Ｈ、Cl、Br、Ｉが好ましい。
ｎは、５〜16の正の整数を表わし、なかでも８
〜16であることが好ましい。
以下に本発明のフタロシアニン化合物の具体例
を挙げる。[Formula] etc.; Halogen-substituted aryl group, such as phenyl chloride group; etc. Y is a hydrogen atom; a halogen atom, such as Cl, Br, I, F, etc.; of these, H, Cl, Br, and I are preferred. n represents a positive integer from 5 to 16, especially 8
-16 is preferred. Specific examples of the phthalocyanine compounds of the present invention are listed below.
【表】【table】
【表】【table】
【表】
本発明のフタロシアニン化合物は、一般に次の
スキームに従う方法で合成することができる。[Table] The phthalocyanine compound of the present invention can generally be synthesized by a method according to the following scheme.
【表】
この方法を用いた場合の反応生成物の精製は次
のように行う。
反応生成物を100℃に冷却し、エタノールで希
釈した後、室温に戻して濾過する。この濾別した
ものをエタノールで洗浄し、さらにエタノール−
水溶液で洗浄し、乾燥する。こうして得られた粗
生成物をシリカカラムでトリエンによつて展開
し、分離して精製する。
発明の具体的作用効果
本発明のフタロシアニン化合物は、
MX−Pc（−SR）o（Ｙ）16-o
で示されるものであるため、近赤外および赤外域
に吸収をもつものが得られる。
従つて、きわめて光や熱に対して堅牢性の高い
近赤外・赤外吸収剤が実現し、光記録媒体や電子
写真感光体用等の吸収剤として有用である。
発明の具体的実施例
以下、本発明の具体的実施例を示し、本発明を
さらに詳細に説明する。
実施例１ 例示化合物(9)の合成
１モルと、エチルメルカプタン（EtSH）４モ
ルとを130℃で２時間で反応させ、
を得た。
この化合物４モル倍にLi+（OC5H11）-2モルを加
えて140℃で２時間反応させ、Li2Pc（−SEt）16を得
た。さらに、この化合物１モルにInCl31モルを加
え、アミルアルコー中で130℃で２時間反応させ、
目的物を得た。得られた反応生成物を100℃に冷
却した後、エタノール（EtOH）で希釈して室温
に戻し、濾過した。濾別したものをEtOHで洗浄
し、さらにEtOH−H2O（１：１）溶液で洗浄し、
乾燥した。このようにして得られた粗生成物をシ
リカカラムでトルエンによつて展開し、分離、精
製して目的物を得た。
収 率 18.5％
元素分析
Ｃ Ｈ Ｎ In
計算値／％ 47.31 4.93 6.90 7.07
実測値／％ 45.98 4.95 6.92 7.05
吸収極大 λmax
830nm（スピンナー塗布により0.1μm厚の薄
膜を形成して測定）
実施例２ 例示化合物(2)の合成
実施例１と同様にして目的物を得た。
収 率 23.4％
元素分析
Ｃ Ｈ Ｎ In
計算値／％ 40.61 2.82 7.90 8.10
実測値／％ 40.79 2.83 7.85 8.04
実施例３ 例示化合物(3)の合成
実施例１と同様にして目的物を得た。
収 率 21.8％
元素分析
Ｃ Ｈ Ｎ Ga
計算値／％ 54.63 2.28 6.37 3.97
実測値／％ 54.95 2.28 6.35 3.99
実施例４ 例示化合物(7)の合成
実施例１と同様にして目的物を得た。
収 率 21.9％
元素分析
Ｃ Ｈ Ｎ In
計算値／％ 48.12 1.74 4.88 5.01
実測値／％ 48.95 1.72 4.82 4.98
実施例５ 例示化合物(10)の合成
２−チオナフトール18モルとKOH18モルとを
キノリン中で140℃にて１時間反応させた。これ
にInClPc（Cl）161モルを加え、160〜180℃にて１
時間反応させた。得られた反応生成物は実施例１
と同様に精製した。
収 率 23.8％
元素分析
Ｃ Ｈ Ｎ In
計算値／％ 72.20 3.51 3.51 3.60
実測値／％ 71.21 3.54 3.52 3.59
吸収極大 λmax
840nm（スピンナー塗布により0.1μm厚の薄
膜を形成して測定）
実施例６ 例示化合物(11)の合成
実施例５と同様にして目的物を得た。
収 率 29.4％
元素分析
Ｃ Ｈ Ｎ Ga
計算値／％ 51.99 6.07 6.07 3.78
実測値／％ 50.92 6.09 6.08 3.74
実施例７ 例示化合物(6)の合成
実施例５と同様にして目的物を得た。
収 率 17.2％
元素分析
Ｃ Ｈ Ｎ Al
計算値／％ 47.44 2.52 5.03 1.21
実測値／％ 47.35 2.53 5.01 1.21
実施例８ 例示化合物(13)の合成
実施例５と同様にして目的物を得た。
収 率 12.8％
元素分析
Ｃ Ｈ Ｎ In
計算値／％ 57.78 1.49 4.65 4.77
実測値／％ 57.92 1.48 4.63 4.75[Table] Purification of the reaction product using this method is carried out as follows. The reaction product is cooled to 100°C, diluted with ethanol, then returned to room temperature and filtered. This filtered material is washed with ethanol, and then ethanol-
Wash with aqueous solution and dry. The crude product thus obtained is developed on a silica column with triene, separated and purified. Specific Effects of the Invention Since the phthalocyanine compound of the present invention is represented by MX-Pc(-SR) o (Y) 16-o , one having absorption in the near-infrared and infrared regions can be obtained. Therefore, near-infrared/infrared absorbers with extremely high fastness to light and heat have been realized, and are useful as absorbers for optical recording media, electrophotographic photoreceptors, and the like. Specific Examples of the Invention Hereinafter, specific examples of the present invention will be shown and the present invention will be explained in further detail. Example 1 Synthesis of exemplified compound (9) 1 mole and 4 moles of ethyl mercaptan (EtSH) were reacted at 130°C for 2 hours, I got it. Li + (OC 5 H 11 ) - 2 mol was added to 4 mol of this compound and reacted at 140°C for 2 hours to obtain Li 2 Pc(-SEt) 16 . Furthermore, 1 mol of InCl 3 was added to 1 mol of this compound and reacted in amyl alcohol at 130°C for 2 hours.
Obtained the object. The obtained reaction product was cooled to 100°C, diluted with ethanol (EtOH), returned to room temperature, and filtered. The filtered material was washed with EtOH, further washed with EtOH-H 2 O (1:1) solution,
Dry. The crude product thus obtained was developed with toluene on a silica column, separated and purified to obtain the desired product. Yield 18.5% Elemental analysis C H N In Calculated value/% 47.31 4.93 6.90 7.07 Actual value/% 45.98 4.95 6.92 7.05 Absorption maximum λmax 830 nm (measured by forming a 0.1 μm thick thin film by spinner coating) Example 2 Exemplary compound Synthesis of (2) The target product was obtained in the same manner as in Example 1. Yield 23.4% Elemental analysis C H N In Calculated value/% 40.61 2.82 7.90 8.10 Actual value/% 40.79 2.83 7.85 8.04 Example 3 Synthesis of exemplified compound (3) The target product was obtained in the same manner as in Example 1. Yield 21.8% Elemental analysis C H N Ga Calculated value/% 54.63 2.28 6.37 3.97 Actual value/% 54.95 2.28 6.35 3.99 Example 4 Synthesis of exemplified compound (7) The target product was obtained in the same manner as in Example 1. Yield 21.9% Elemental analysis C H N In Calculated value/% 48.12 1.74 4.88 5.01 Actual value/% 48.95 1.72 4.82 4.98 Example 5 Synthesis of exemplified compound (10) 18 moles of 2-thionaphthol and 18 moles of KOH were dissolved in quinoline. The reaction was carried out at 140°C for 1 hour. Add 1 mol of InClPc(Cl) 16 to this and
Allowed time to react. The obtained reaction product is Example 1
It was purified in the same way. Yield 23.8% Elemental analysis C H N In Calculated value/% 72.20 3.51 3.51 3.60 Actual value/% 71.21 3.54 3.52 3.59 Absorption maximum λmax 840 nm (measured by forming a 0.1 μm thick thin film by spinner coating) Example 6 Exemplary compound Synthesis of (11) The target product was obtained in the same manner as in Example 5. Yield 29.4% Elemental analysis C H N Ga Calculated value/% 51.99 6.07 6.07 3.78 Actual value/% 50.92 6.09 6.08 3.74 Example 7 Synthesis of exemplified compound (6) The target product was obtained in the same manner as in Example 5. Yield 17.2% Elemental analysis C H N Al Calculated value/% 47.44 2.52 5.03 1.21 Actual value/% 47.35 2.53 5.01 1.21 Example 8 Synthesis of exemplified compound (13) The target product was obtained in the same manner as in Example 5. Yield 12.8% Elemental analysis C H N In Calculated value/% 57.78 1.49 4.65 4.77 Actual value/% 57.92 1.48 4.63 4.75
Claims (1)
素原子数６〜24のアリール基、アルキルアリール
基、アルコキシアリール基もしくはハロゲン置換
アリール基を表わす。 Ｙは、水素原子またはハロゲン原子を表わす。 ｎは、５〜16の正の整数を表わす。｝ で示されることを特徴とするフタロシアニン化合
物。[Claims] 1 Formula MX-Pc(-SR) o (Y) 16-o {wherein M represents Al, Ga or In. X represents a halogen atom. Pc represents a phthalocyanine nucleus. R represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 24 carbon atoms, an alkylaryl group, an alkoxyaryl group, or a halogen-substituted aryl group. Y represents a hydrogen atom or a halogen atom. n represents a positive integer from 5 to 16. } A phthalocyanine compound characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28119184A JPH0244475B2 (en) | 1984-12-27 | 1984-12-27 | FUTAROSHIANIN KAGOBUTSU |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28119184A JPH0244475B2 (en) | 1984-12-27 | 1984-12-27 | FUTAROSHIANIN KAGOBUTSU |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61152685A JPS61152685A (en) | 1986-07-11 |
| JPH0244475B2 true JPH0244475B2 (en) | 1990-10-04 |
Family
ID=17635612
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28119184A Expired - Lifetime JPH0244475B2 (en) | 1984-12-27 | 1984-12-27 | FUTAROSHIANIN KAGOBUTSU |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0244475B2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0631239B2 (en) * | 1987-04-06 | 1994-04-27 | 株式会社日本触媒 | Novel fluorine-containing phthalocyanine compound and method for producing the same |
| JPH0721118B2 (en) * | 1987-06-26 | 1995-03-08 | 日立化成工業株式会社 | Naphthalocyanine derivative, method for producing the same, optical recording medium using the same, and method for producing the optical recording medium |
| JP3077458B2 (en) * | 1993-07-23 | 2000-08-14 | 東洋インキ製造株式会社 | Method for producing aluminum phthalocyanine composition |
| EP0718375B1 (en) * | 1994-12-21 | 2000-07-05 | Mitsui Chemicals, Inc. | Near infrared absorber, preparation process thereof and use thereof |
| JP6016507B2 (en) * | 2012-08-02 | 2016-10-26 | 株式会社日本触媒 | Phthalocyanine compound and infrared cut filter containing the same |
-
1984
- 1984-12-27 JP JP28119184A patent/JPH0244475B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61152685A (en) | 1986-07-11 |
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