JPH0615670B2 - Near infrared absorber and optical recording medium using the same - Google Patents
Near infrared absorber and optical recording medium using the sameInfo
- Publication number
- JPH0615670B2 JPH0615670B2 JP62262595A JP26259587A JPH0615670B2 JP H0615670 B2 JPH0615670 B2 JP H0615670B2 JP 62262595 A JP62262595 A JP 62262595A JP 26259587 A JP26259587 A JP 26259587A JP H0615670 B2 JPH0615670 B2 JP H0615670B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- unsubstituted
- alkyl
- optical recording
- 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
Classifications
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
- G11B7/248—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes porphines; azaporphines, e.g. phthalocyanines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
- C09B47/0673—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having alkyl radicals linked directly to the Pc skeleton; having carbocyclic groups linked directly to the skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
- C09B47/0675—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having oxygen or sulfur linked directly to the skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
- C09B47/0676—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having nitrogen atom(s) linked directly to the skeleton
Description
【発明の詳細な説明】 〔産業上の利用分野〕 近年、近赤外線領域の光を利用したエネルギーシステ
ム、情報記録システム、機器のコントロールシステムが
多数開発されている。本発明の化合物はこれらのシステ
ムに利用出来る近赤外線吸収剤に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial field of application] In recent years, a number of energy systems, information recording systems, and device control systems utilizing light in the near infrared region have been developed. The compounds of the present invention relate to near infrared absorbers that can be used in these systems.
更に詳しくは、光記録媒体、有機感光体、光カード、テ
レビ・音響機器などの制御機構の光吸収あるいは外部近
赤外光遮断、レーザー加工用保護メガネ、熱線遮断によ
る成長制御などの分野に利用出来る化合物を関する。More specifically, it is used in fields such as optical recording media, organic photoconductors, optical cards, optical absorption of control mechanisms such as televisions and audio equipment, external near infrared light blocking, protective glasses for laser processing, growth control by heat ray blocking, etc. It relates to compounds that can.
〔従来の技術〕 ナフタロシアニンを用いた光記録媒体としては、米国特
許4492750号が樹脂とナフタロシアニンを混合した記録
膜を開示している。[Prior Art] As an optical recording medium using naphthalocyanine, US Pat. No. 4,492,750 discloses a recording film in which a resin and naphthalocyanine are mixed.
反射層を有し、吸熱層にナフタロシアニンを用いた記録
媒体が特開昭61-163891 、61-163892 に記載がある。Recording media having a reflective layer and using naphthalocyanine for the endothermic layer are described in JP-A-61-163891 and 61-163892.
しかし、一般的にナフタロシアニンを単独で用いた膜は
反射率が低く、実用性に欠けていた。However, in general, a film using naphthalocyanine alone has a low reflectance and is not practical.
反射率が向上した例として特開昭61-235188 号がある
が、色素の耐久性が悪くなり、やはり実用上問題であっ
た。JP-A-61-235188 is an example of an improved reflectance, but the durability of the dye is deteriorated, which is also a problem in practical use.
本発明は上記の問題点を解決すべくなされたもので、反
射率が高く、かつ耐久性の優れた色素であって、加工時
の欠陥率の小さいナフタロシアニン化合物を提供するこ
とを目的とする。The present invention has been made to solve the above problems, and an object of the present invention is to provide a naphthalocyanine compound having a high reflectance and an excellent durability, and having a small defect rate during processing. .
本発明者らはジナフタロシアニンが近赤外光吸収色素と
して優れかつ適度な溶解性、樹脂との相溶性を有し、耐
久性にも優れていることを見い出し本発明の完成に至っ
た。The present inventors have found that dinaphthalocyanine is excellent as a near-infrared light absorbing dye, has appropriate solubility and compatibility with a resin, and is also excellent in durability, and completed the present invention.
すなわち本発明は、４価の中心元素に対して２個のナフ
タロシアニン環が結合してなることを特徴とする下式
（Ｉ）で示されるジナフタロシアニン近赤外線吸収剤お
よびその互変異性体である。That is, the present invention relates to a dinaphthalocyanine near-infrared absorber represented by the following formula (I) and a tautomer thereof, characterized in that two naphthalocyanine rings are bonded to a tetravalent central element. is there.
式（Ｉ）中、ナフタレン環Ａ，Ｂ，Ｃ，Ｄ，Ｅ，Ｆ，
Ｇ，Ｈは、各々独立に無置換であるか、無置換もしくは
ハロゲン、アルキルチオ、アルキル置換フェノキシ基で
置換されたアルキル基；無置換もしくはアルコキシで置
換されたアルコキシ基；無置換もしくはアルコキシ基で
置換されたアルキルチオ基；アルキルアミノ基；フェニ
ル基；アルキルフェニル基；ナフチル基；無置換もしく
はアルキル置換フェノキシ基；ナフトキシ基；無置換ま
たはアルキル置換フェニルチオ基；ナフチルチオ基；フ
ェニルアミノ基；ハロゲンから選ばれる基で置換してい
てもよく、[Met]4+はスズ、ケイ素、ゲルマニウムを表
す。〕 また他の発明はそれを含む記録層を有する光記録媒体で
ある。 In the formula (I), naphthalene rings A, B, C, D, E, F,
G and H are each independently unsubstituted or unsubstituted or substituted with a halogen, an alkylthio, or an alkyl-substituted phenoxy group; an unsubstituted or alkoxy-substituted alkoxy group; an unsubstituted or substituted alkoxy group Alkylthio group; phenyl group; alkylphenyl group; naphthyl group; unsubstituted or alkyl-substituted phenoxy group; naphthoxy group; unsubstituted or alkyl-substituted phenylthio group; naphthylthio group; phenylamino group; group selected from halogen May be substituted with, and [Met] 4+ represents tin, silicon, or germanium. Another invention is an optical recording medium having a recording layer containing the same.
式（Ｉ）で示される化合物の各ナフタレン環に置換して
もよいアルキル基の例としては、炭素数１〜20の直鎖又
は分岐のアルキル基、好ましくは１〜８の直鎖又は分岐
のアルキル基；β−クロルエチル基、ペンチルフロロプ
ロピル基、ヨウ化ブチル基、臭化プロピル基、パーフロ
ロアルキル基などのハロゲン化アルキル基；エチルチオ
エチル基、フェニルチオエチル基、メチルチオブチル基
などのアルキルチオアルキル基などが挙げられる。Examples of the alkyl group which may be substituted on each naphthalene ring of the compound represented by the formula (I) include a linear or branched alkyl group having 1 to 20 carbon atoms, preferably a linear or branched alkyl group having 1 to 8 carbon atoms. Alkyl group: Halogenated alkyl group such as β-chloroethyl group, pentylfluoropropyl group, butyl iodide group, propyl bromide group, perfluoroalkyl group; Alkylthio such as ethylthioethyl group, phenylthioethyl group, methylthiobutyl group An alkyl group etc. are mentioned.
アルコキシ基の例としては、メトキシ基、エトキシ基、
プロポキシ基、ブトキシ基、ペントキシ基、ヘキシルオ
キシ基、ヘプチルオキシ基、オクチルオキシ基のような
炭素数１〜20の分岐又は直鎖の炭化水素オキシ基；メト
キシエトキシ基、エトキシエトキシ基、プロポキシエト
キシ基、ブトキシエトキシ基、フェノキシエトキシ基、
メトキシエトキシエトキシ基、エトキシエトキシエトキ
シ基、メトキシエトキシエトキシエトキシ基、などが挙
げられる。Examples of the alkoxy group include methoxy group, ethoxy group,
A branched or linear hydrocarbon oxy group having 1 to 20 carbon atoms such as a propoxy group, a butoxy group, a pentoxy group, a hexyloxy group, a heptyloxy group, an octyloxy group; a methoxyethoxy group, an ethoxyethoxy group, a propoxyethoxy group. , Butoxyethoxy group, phenoxyethoxy group,
Examples thereof include a methoxyethoxyethoxy group, an ethoxyethoxyethoxy group, and a methoxyethoxyethoxyethoxy group.
置換又は無置換のアルキルチオ基の例としては、メチル
チオ基、エチルチオ基などの炭素数１〜30の直鎖又は分
岐の炭化水素チオ基；メトキシメチルチオ基、メトキシ
エチルチオ基、エトキシエチルチオ基、ブトキシエチル
チオ基、メトキシエトキシエチルチオ基などのオリゴア
ルコキシアルキルチオ基；などが挙げられる。Examples of the substituted or unsubstituted alkylthio group include a linear or branched hydrocarbon thio group having 1 to 30 carbon atoms such as methylthio group and ethylthio group; methoxymethylthio group, methoxyethylthio group, ethoxyethylthio group, butoxy. Examples thereof include oligoalkoxyalkylthio groups such as ethylthio group and methoxyethoxyethylthio group.
置換又は無置換のアルキルアミノ基又はジアルキルアミ
ノ基の例としては、メチルアミノ基、エチルアミノ基、
N,N-ジメチルアミノ基、N,N-ジエチルアミノ基などの総
炭素数１〜30の直鎖又は分岐のアルキル基置換アミノ
基；などが挙げられる。また各々の置換基は連結基で結
ばれていてもよい。Examples of the substituted or unsubstituted alkylamino group or dialkylamino group include a methylamino group, an ethylamino group,
And a linear or branched alkyl group-substituted amino group having a total of 1 to 30 carbon atoms such as N, N-dimethylamino group and N, N-diethylamino group. Moreover, each substituent may be connected by a linking group.
本発明の式（Ｉ）で示される化合物は次のようにして製
造される。すなわち、次式（II）又は（III） 〔式（II）及び式（III）のナフタレン環は、前述の式
（Ｉ）のナフタレン環Ａ〜Ｈと同じ置換基で置換されて
いてもよい〕 の１〜４種をアルコール類中アルカリ金属アルコキシド
と加熱反応して得たナフタロシアニンアルカリ金属塩と
テトラクロルスズ、テトラクロルゲルマニウム、テトラ
クロルケイ素又はテトラクロルチタンと反応させて得る
か、あるいは（II）又は（III）の化合物とテトラクロ
ルスズ、テトラクロルゲルマニウム、テトラクロルケイ
素又はテトラクロルチタンとをキノリン中塩基の存在下
に反応させて合成したジクロルスズナフタロシアニン、
ジクロルゲルマニウムナフタロシアニン、ジクロルケイ
素ナフタロシアニン又はジクロルチタンナフタロシアニ
ンを上述のアルカリ金属ナフタロシアニンと反応するこ
とにより得られる。The compound of formula (I) of the present invention is produced as follows. That is, the following formula (II) or (III) [The naphthalene rings of the formulas (II) and (III) may be substituted with the same substituents as the naphthalene rings A to H of the above formula (I)]. Naphthalocyanine alkali metal salt obtained by heating reaction with alkoxide and tetrachlorotin, tetrachlorogermanium, tetrachlorosilicon or tetrachlorotitanium, or a compound of (II) or (III) and tetrachlorotin Dichlorotin naphthalocyanine synthesized by reacting tetrachlorogermanium, tetrachlorosilicon or tetrachlorotitanium in quinoline in the presence of a base,
It is obtained by reacting dichlorogermanium naphthalocyanine, dichlorosilicon naphthalocyanine or dichlorotitanium naphthalocyanine with the above-mentioned alkali metal naphthalocyanine.
本発明の色素を用いて光記録媒体を製造する方法として
は、透明基板上に色素を塗布或いは蒸着する方法があ
り、塗布法としては、バインダー樹脂20重量％以下、好
ましくは０％と、色素0.05重量％〜20重量％、好ましく
は０．５重量％〜20重量％となるように溶媒に溶解し、
スピンコーターで塗布する方法などがある。又蒸着方法
としては、10-5〜10-7torr、100〜300℃にて基板上に色
素をのせる方法などがある。As a method for producing an optical recording medium using the dye of the present invention, there is a method of coating or vapor depositing a dye on a transparent substrate. The coating method is 20% by weight or less of a binder resin, preferably 0%. 0.05 wt% to 20 wt%, preferably 0.5 wt% to 20 wt% dissolved in a solvent,
There is a method of applying with a spin coater. As a vapor deposition method, there is a method of placing a dye on a substrate at 10 -5 to 10 -7 torr and 100 to 300 ° C.
基板としては、光学的に透明な樹脂であればよい。例え
ばアクリル樹脂、ポリエチレン樹脂、塩化ビニール樹
脂、塩化ビニリデン樹脂、ポリカーボネイト樹脂、エチ
レン樹脂、ポリオレフィン共重合樹脂、塩化ビニール共
重合樹脂、塩化ビニリデン共重合樹脂、スチレン共重合
樹脂などが挙げられる。The substrate may be any optically transparent resin. Examples thereof include acrylic resin, polyethylene resin, vinyl chloride resin, vinylidene chloride resin, polycarbonate resin, ethylene resin, polyolefin copolymer resin, vinyl chloride copolymer resin, vinylidene chloride copolymer resin, and styrene copolymer resin.
又基板は熱硬化性樹脂又は紫外線硬化性樹脂により表面
処理がなされていてもよい。The substrate may be surface-treated with a thermosetting resin or an ultraviolet curable resin.
塗布溶媒としては、ハロゲン化炭化水素（例えば、ジク
ロロメタン、クロロホルム、塩化炭素、テトラクロロエ
チレン、ジクロロジフロロエタンなど）、エーテル類
（例えば、テトラヒドロフラン、ジエチルエーテルな
ど）、ケトン類（例えば、アセトン、メチルエチルケト
ンなど）、アルコール類、（例えば、メタノール、エタ
ノール、プロパノールなど）、セロソルプ類（メチルセ
ロソルブ、エチルセロソルブなど）、炭化水素類（ヘキ
サン、シクロヘキサン、オクタン、ベンゼン、トルエ
ン、キシレンなど）が好適に用いられる。As the coating solvent, halogenated hydrocarbons (eg, dichloromethane, chloroform, carbon chloride, tetrachloroethylene, dichlorodifluoroethane, etc.), ethers (eg, tetrahydrofuran, diethyl ether, etc.), ketones (eg, acetone, methyl ethyl ketone, etc.) , Alcohols (eg, methanol, ethanol, propanol, etc.), cellosolves (methyl cellosolve, ethyl cellosolve, etc.), and hydrocarbons (hexane, cyclohexane, octane, benzene, toluene, xylene, etc.) are preferably used.
実施例１ 6-アミル-2,3- ジシアノナフタレン 248重量部、塩化第
２スズ65重量部をキノリン1000重量部、トリブチルアミ
ン1000重量部中 200℃にて３時間反応させ、室温に冷却
後、メタノール5000重量部に排出した。析出した結晶を
濾別し、メタノール洗浄し、ジクロロスズナフタロシア
ニン100 重量部を得た。一方、6-アミル-2,3- ジシアノ
ナフタレン 248重量部、N,N-ジメチルアミノエタノール
1000重量部、ＤＢＵ 200重量部とナトリウム12重量部を
加熱還流し、系中にナトリウムナフタロシアニンを生成
させた。続いて上述のジクロロスズナフタロシアニン 2
00重量部を加え、３時間還流させた。析出した結晶を濾
別し、スズジナフタロシアニンを得た。λmax ： 785ｎ
ｍ（CHCl３中）。Example 1 248 parts by weight of 6-amyl-2,3-dicyanonaphthalene and 65 parts by weight of stannic chloride were reacted in 1000 parts by weight of quinoline and 1000 parts by weight of tributylamine at 200 ° C. for 3 hours, and after cooling to room temperature, It was discharged to 5000 parts by weight of methanol. The precipitated crystals were separated by filtration and washed with methanol to obtain 100 parts by weight of dichlorotin naphthalocyanine. On the other hand, 248 parts by weight of 6-amyl-2,3-dicyanonaphthalene, N, N-dimethylaminoethanol
1000 parts by weight, 200 parts by weight of DBU and 12 parts by weight of sodium were heated under reflux to generate sodium naphthalocyanine in the system. Then, the above-mentioned dichlorotin naphthalocyanine 2
00 parts by weight was added and the mixture was refluxed for 3 hours. The precipitated crystals were separated by filtration to obtain tin dinaphthalocyanine. λ max: 785n
m (in CHCl 3).
上述のスズジナフタロシアニン１重量部をクロロホルム
1000重量部に溶解し、ガラス基板上にスピンコートし
た。得られた光記録媒体は高感度であった。又反射率は
830ｎｍで25％であった。Chloroform was added to 1 part by weight of the above tin dinaphthalocyanine.
It was dissolved in 1000 parts by weight and spin-coated on a glass substrate. The obtained optical recording medium had high sensitivity. The reflectance is
It was 25% at 830 nm.
実施例２ 2,3- ジシアノナフタレンを用いて実施例１と同様にし
てスズジナフタロシアニンを合成した。Example 2 Tin dinaphthalocyanine was synthesized in the same manner as in Example 1 using 2,3-dicyanonaphthalene.
10-10torr、200℃にてポリカーボネート基板に蒸着し
た。この光記録媒体は反射率35％であり、良好な記録特
性を有していた。It was vapor-deposited on a polycarbonate substrate at 10 -10 torr and 200 ° C. This optical recording medium had a reflectance of 35% and had good recording characteristics.
実施例３ 6-エトキシエトキシエトキシ-2,3- ナフタレンジニトリ
ルを用いて実施例１と同様にしてジクロロスズナフタロ
シアニンを得た。一方、エタノール中ナトリウム存在下
に6-エトキシエトキシエトキシ-2,3- ナフタレンジニト
リルを加熱還流することにより系中にナトリウムナフタ
ロシアニンを合成した。続いて上述のジクロロスズナフ
タロシアニンを加えて加熱還流し、次いで溶媒を留去す
ることによりスズジナフタロシアニンを得た。Example 3 Dichlorotin naphthalocyanine was obtained in the same manner as in Example 1 using 6-ethoxyethoxyethoxy-2,3-naphthalenedinitrile. On the other hand, sodium naphthalocyanine was synthesized in the system by heating and refluxing 6-ethoxyethoxyethoxy-2,3-naphthalenedinitrile in the presence of sodium in ethanol. Subsequently, the above-mentioned dichlorotin naphthalocyanine was added and heated under reflux, and then the solvent was distilled off to obtain tin dinaphthalocyanine.
λmax(エチルセロソルブ中)＝790nm。λmax (in ethyl cellosolve) = 790 nm.
この化合物をエチルセロソルブに溶解し、ポリカーボネ
ート基板上で塗布して光記録媒体を得た。反射率25％で
あった。This compound was dissolved in ethyl cellosolve and coated on a polycarbonate substrate to obtain an optical recording medium. The reflectance was 25%.
実施例４ 6-(p-tert-ブチルフェニルチオ)-2,3-ナフタレンジニト
リル 300重量部をエタノール中金属ナトリウム15重量部
と反応させ、ナトリウムナフタロシアニンを系中に生成
させた。続いて塩化第２スズ30重量部を加え、加熱還流
した。溶媒を留去した後精製してスズジナフタロシアニ
ンを得た。Example 4 300 parts by weight of 6- (p-tert-butylphenylthio) -2,3-naphthalenedinitrile was reacted with 15 parts by weight of metallic sodium in ethanol to form sodium naphthalocyanine in the system. Subsequently, 30 parts by weight of stannic chloride was added, and the mixture was heated under reflux. After distilling off the solvent, purification was performed to obtain tin dinaphthalocyanine.
λmax(ベンゼン中)＝810ｎｍ。λmax (in benzene) = 810 nm.
実施例１〜４によって得られた化合物の反射率と、これ
らを用いた光記録媒体の耐久性、加工性についての結果
を表−１に示した。表中には比較例として公知化合物３
種についても示した。Table 1 shows the reflectances of the compounds obtained in Examples 1 to 4 and the results of the durability and processability of the optical recording medium using them. In the table, as a comparative example, known compound 3
The species is also shown.
○ は良好 × は不良 を表わす。◯ means good x means bad.
1) 米国特許4492750 の色素 2) 特開昭61-163891 の色素 3) 特開昭61-235188 の色素 実施例５〜40 下記一般式（IV）の中間体（表−２の１〜21で表わされ
る中間体）１〜８種を用いて実施例４と同様にしてス
ズ、ゲルマニウム及びケイ素のジナフタロシアニンを合
成した。 1) U.S. Pat. No. 4,492,750 2) Dye of JP-A-61-163891 3) Dye of JP-A-61-235188 Examples 5 to 40 Using the intermediates of the following general formula (IV) (the intermediates represented by 1 to 21 in Table 2) 1 to 8 in the same manner as in Example 4, tin, germanium and silicon dinaphthalocyanine Was synthesized.
異なる中間体、金属より得られた化合物のλmax を表−
３に示す。これらの色素を用いた光記録媒体は高い反射
率と良好な感度を示した。 Show λmax of compounds obtained from different intermediates and metals
3 shows. Optical recording media using these dyes have high reflectance and good sensitivity.
〔発明の効果〕 本発明の近赤外線吸収剤は耐湿性、耐光性に優れてお
り、又光記録媒体を製造する時の取り扱い（加工性）に
優れている。 [Advantages of the Invention] The near-infrared absorber of the present invention is excellent in moisture resistance and light resistance, and is also excellent in handling (processability) when manufacturing an optical recording medium.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 中塚 正勝 神奈川県横浜市栄区飯島町2882 (72)発明者 榎本 堅 神奈川県横須賀市津久井180 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Masakatsu Nakatsuka 2882 Iijima-cho, Sakae-ku, Yokohama-shi, Kanagawa Prefecture (72) Ken Enomoto 180 Tsukui, Yokosuka-shi, Kanagawa Prefecture
Claims (2)
Ｇ，Ｈは、各々独立に無置換であるか、無置換もしくは
ハロゲン、アルキルチオ、アルキル置換フェノキシ基で
置換されたアルキル基；無置換もしくはアルコキシで置
換されたアルコキシ基；無置換もしくはアルコキシ基で
置換されたアルキルチオ基；アルキルアミノ基；フェニ
ル基；アルキルフェニル基；ナフチル基；無置換もしく
はアルキル置換フェノキシ基；ナフトキシ基；無置換ま
たはアルキル置換フェニルチオ基；ナフチルチオ基；フ
ェニルアミノ基；ハロゲンから選ばれる基で置換してい
てもよく、[Met]4+はスズ、ケイ素、ゲルマニウムを表
す。〕 で示されるジナフタロシアニン近赤外線吸収剤及びその
互変異性体。1. The following formula (I) [In the formula (I), a naphthalene ring A, B, C, D, E, F,
G and H are each independently unsubstituted or unsubstituted or substituted with a halogen, an alkylthio, or an alkyl-substituted phenoxy group; an unsubstituted or alkoxy-substituted alkoxy group; an unsubstituted or substituted alkoxy group Alkylthio group; phenyl group; alkylphenyl group; naphthyl group; unsubstituted or alkyl-substituted phenoxy group; naphthoxy group; unsubstituted or alkyl-substituted phenylthio group; naphthylthio group; phenylamino group; group selected from halogen May be substituted with, and [Met] 4+ represents tin, silicon, or germanium. ] The dinaphthalocyanine near-infrared absorber and its tautomer shown by these.
Ｇ，Ｈは、各々独立に無置換であるか、無置換もしくは
ハロゲン、アルキルチオ、アルキル置換フェノキシ基で
置換されたアルキル基；無置換もしくはアルコキシで置
換されたアルコキシ基；無置換もしくはアルコキシ基で
置換されたアルキルチオ基；アルキルアミノ基；フェニ
ル基；アルキルフェニル基；ナフチル基；無置換もしく
はアルキル置換フェノキシ基；ナフトキシ基；無置換ま
たはアルキル置換フェニルチオ基；ナフチルチオ基；フ
ェニルアミノ基；ハロゲンから選ばれる基で置換してい
てもよく、[Met]4+はスズ、ケイ素、ゲルマニウムを表
す。〕 で示されるジナフタロシアニン近赤外線吸収剤及びその
互変異性体を記録層に含有する光記録媒体。2. The following formula (I) [In the formula (I), a naphthalene ring A, B, C, D, E, F,
G and H are each independently unsubstituted or unsubstituted or substituted with a halogen, an alkylthio, or an alkyl-substituted phenoxy group; an unsubstituted or alkoxy-substituted alkoxy group; an unsubstituted or substituted alkoxy group Alkylthio group; phenyl group; alkylphenyl group; naphthyl group; unsubstituted or alkyl-substituted phenoxy group; naphthoxy group; unsubstituted or alkyl-substituted phenylthio group; naphthylthio group; phenylamino group; group selected from halogen May be substituted with, and [Met] 4+ represents tin, silicon, or germanium. ] An optical recording medium containing a dinaphthalocyanine near-infrared absorber represented by and its tautomer in a recording layer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62262595A JPH0615670B2 (en) | 1987-10-20 | 1987-10-20 | Near infrared absorber and optical recording medium using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62262595A JPH0615670B2 (en) | 1987-10-20 | 1987-10-20 | Near infrared absorber and optical recording medium using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01108264A JPH01108264A (en) | 1989-04-25 |
| JPH0615670B2 true JPH0615670B2 (en) | 1994-03-02 |
Family
ID=17377982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62262595A Expired - Lifetime JPH0615670B2 (en) | 1987-10-20 | 1987-10-20 | Near infrared absorber and optical recording medium using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0615670B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07118273A (en) * | 1993-10-22 | 1995-05-09 | Hiroyoshi Shirai | Naphthalocyanine compound, its production, naphthalocyanine polymer and its production |
| US7470315B2 (en) | 2005-07-05 | 2008-12-30 | Silverbrook Research Pty Ltd | Red-shifted water dispersible napthalocyanine dyes |
| JP7128804B2 (en) | 2017-04-07 | 2022-08-31 | 山本化成株式会社 | Naphthalocyanine compound, production method and use thereof |
-
1987
- 1987-10-20 JP JP62262595A patent/JPH0615670B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01108264A (en) | 1989-04-25 |
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