JPH0742411B2 - Anthraquinone long-wavelength absorption dye - Google Patents
Anthraquinone long-wavelength absorption dyeInfo
- Publication number
- JPH0742411B2 JPH0742411B2 JP60132036A JP13203685A JPH0742411B2 JP H0742411 B2 JPH0742411 B2 JP H0742411B2 JP 60132036 A JP60132036 A JP 60132036A JP 13203685 A JP13203685 A JP 13203685A JP H0742411 B2 JPH0742411 B2 JP H0742411B2
- Authority
- JP
- Japan
- Prior art keywords
- dye
- anthraquinone
- formula
- long
- wavelength absorption
- 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 - Fee Related
Links
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title claims description 6
- 238000010521 absorption reaction Methods 0.000 title claims description 5
- 150000004056 anthraquinones Chemical class 0.000 title claims description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000000975 dye Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 230000003595 spectral effect Effects 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 229920006267 polyester film Polymers 0.000 description 6
- QJQPINQAQJTYMH-UHFFFAOYSA-N 5,8,9,10-tetrahydroxy-2,3-dihydroanthracene-1,4-dione Chemical compound O=C1CCC(=O)C2=C1C(O)=C1C(O)=CC=C(O)C1=C2O QJQPINQAQJTYMH-UHFFFAOYSA-N 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 5
- 239000004327 boric acid Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 3
- 239000001046 green dye Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- -1 anthraquinone compound Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940126540 compound 41 Drugs 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
- G03C1/83—Organic dyestuffs therefor
-
- 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
- G11B7/245—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 a polymeric component
-
- 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
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
- G11B7/2532—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising metals
-
- 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
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
- G11B7/2533—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Optical Filters (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、長波長吸収色素に関する。特に、カラーフィ
ルターに用いるのに有用な、700〜800nmに吸収極大波長
を有するアントラキノン系緑色色素に関する。TECHNICAL FIELD The present invention relates to a long-wavelength absorbing dye. In particular, it relates to an anthraquinone-based green dye having an absorption maximum wavelength at 700 to 800 nm, which is useful for a color filter.
長波長吸収色素の用途としては、レーザー用フィルタ
ー、カラーディスプレー用の微細色分解フィルター用等
に使用されている。The long-wavelength absorbing dyes are used for laser filters, fine color separation filters for color displays and the like.
上記分野に用いる公知の色素としては、例えば特開昭59
−26293号記載の、下記の一般式で示されるアントラキ
ノン系化合物 、特開昭59−199291号、59−199292号、60−15458号記
載の、下記一般式で示されるナフトキノン系化合物が知
られている。Known dyes used in the above fields include, for example, JP-A-59
-26293, an anthraquinone compound represented by the following general formula Also known are naphthoquinone compounds represented by the following general formula, which are described in JP-A-59-199291, 59-199292 and 60-15458.
〔発明が解決しようとする課題〕 しかし、これらの化合物はその製造工程は複雑多岐にわ
たり、さらに有害ガス等の発生や、一般的に収率が低い
ことなどがあり、工業的に製造するには不利な化合物で
あった。また、緑色カラーフィルター用色素としては、
分光特性が不十分であった。 [Problems to be Solved by the Invention] However, these compounds have complicated and diversified manufacturing processes, and further, generation of harmful gases and the like, and generally low yield, and thus industrial production It was a disadvantageous compound. Also, as the dye for the green color filter,
The spectral characteristics were insufficient.
本発明の目的は、カラーフィルターに適した、分光特性
に優れた緑色色素を設計および提供することにある。An object of the present invention is to design and provide a green dye suitable for a color filter and having excellent spectral characteristics.
本発明者らは、上記の目的を達成するために鋭意検討し
た結果、700〜800nmに吸収極大を有する緑色色素であ
る、下記一般式（Ｉ）で示される化合物が、本発明の目
的を満たし得ることを見出して本発明を完成するに至っ
た。The present inventors have conducted intensive studies to achieve the above object, and as a result, a compound represented by the following general formula (I), which is a green dye having an absorption maximum at 700 to 800 nm, satisfies the object of the present invention. The present invention has been completed by finding that it can be obtained.
すなわち、本発明は、一般式（Ｉ） 〔式中、ベンゼン核Ａ、Ｂ、Ｃ、Ｄのうち少なくとも一
つ以上がハロゲン原子で置換され、残りのベンゼン核は
それぞれ同一または独立に、低級アルキル基で置換され
ていてもよい。〕 で示されるアントラキノン系長波長吸収色素に関するも
のであり、更にはカラーフィルターに用いられることを
特徴とする該色素に関するものである。That is, the present invention has the general formula (I) [In the formula, at least one or more of the benzene nuclei A, B, C, and D may be substituted with a halogen atom, and the remaining benzene nuclei may be identically or independently substituted with a lower alkyl group. ] The present invention relates to an anthraquinone-based long wavelength absorption dye, and further relates to the dye, which is used in a color filter.
一般式（Ｉ）中、ベンゼン核Ａ、Ｂ、Ｃ、Ｄに置換して
もよい置換基としては、フッ素原子、塩素原子、臭素原
子などのハロゲン原子、メチル基、エチル基、ｎ−プロ
ピル基、イソプロピル基、ｎ−ブチル基、イソブチル
基、sec−ブチル基、tert−ブチル基などの炭素数１〜
４の低級アルキル基などが挙げられ、好ましくは、炭素
数１〜３の低級アルキル基、塩素原子である。In the general formula (I), the substituents that may be substituted on the benzene nuclei A, B, C and D include halogen atoms such as fluorine atom, chlorine atom and bromine atom, methyl group, ethyl group, n-propyl group. , Isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, etc.
And a lower alkyl group having 4 to 4 carbon atoms, preferably a lower alkyl group having 1 to 3 carbon atoms and a chlorine atom.
本発明の一般式（Ｉ）で示される色素を製造する方法と
しては、ロイコ−1,4,5,8−テトラヒドロキシアントラ
キノンに対して、４〜50倍モルの式（II）〜（Ｖ） 〔式（II）〜（Ｖ）中のベンゼン核Ａ〜Ｄは、式（Ｉ）
のベンゼン核Ａ〜Ｄと同じ。〕 で表される一種又は二種以上のアニリン誘導体を、自溶
媒または溶媒の存在下、ホウ酸と鉱酸、及び亜鉛の存在
下、50〜300℃、好ましくは100〜200℃にて加熱反応さ
せることにより、前記式（Ｉ）で表される色素を得るこ
とができる。The method for producing the dye represented by the general formula (I) of the present invention is as follows: leuco-1,4,5,8-tetrahydroxyanthraquinone in 4 to 50 moles of the formulas (II) to (V). [The benzene nuclei A to D in the formulas (II) to (V) are represented by the formula (I)
Same as benzene nuclei A to D. ] One or two or more aniline derivatives represented by, in the presence of self-solvent or solvent, boric acid and mineral acid, and in the presence of zinc, at 50 ~ 300 ℃, heating reaction at 100 ~ 200 ℃, preferably By doing so, the dye represented by the above formula (I) can be obtained.
本発明の色素を用いてカラーフィルターを得る方法とし
ては、公知方法、すなわちアルミナゲルなどを塗布、焼
成した透明基材や、透明樹脂（アクリル樹脂、塩化ビニ
ル樹脂、ポリエステル樹脂、ポリオレフィン樹脂等）基
材に本発明の色素を塗布、染色または蒸着させる方法、
あるいは樹脂に本発明の色素を練り込み加工するなどの
方法がある。As a method for obtaining a color filter using the dye of the present invention, a known method, that is, a transparent substrate coated with alumina gel or the like and baked, or a transparent resin (acrylic resin, vinyl chloride resin, polyester resin, polyolefin resin, etc.) group A method of coating, dyeing or vapor depositing the dye of the present invention on a material,
Alternatively, there is a method of kneading and processing the dye of the present invention in a resin.
以下、実施例により本発明を具体的に説明する。 Hereinafter, the present invention will be specifically described with reference to examples.
実施例１ ロイコ−1,4,5,8−テトラヒドロキシアントラキノン24
g、ｐ−クロロアニリン180g、ホウ酸5g、35％酸塩10g
と、亜鉛2gを混合し、150℃で５時間反応させた。反応
後80℃に冷却し、メタノール500mlに排出し、濾過、洗
浄、ピリジンで再結晶した後乾燥し、下式（Ａ） 元素分析値 Ｃ Ｈ Ｎ Cl 実測値 65.53％ 3.34％ 7.87％ 19.55％ 計算値 64.24％ 3.40％ 7.89％ 19.96％ の化合物39g（収率63％）を得た。λmax（クロロホル
ム）＝745nmであった。また、クロロホルム中での透過
率は700nmで５％、600nmで49％、550nmで73％、500nmで
82％、480nmで84％、400nmで42％であった。Example 1 Leuco-1,4,5,8-tetrahydroxyanthraquinone 24
g, p-chloroaniline 180g, boric acid 5g, 35% acid salt 10g
And 2 g of zinc were mixed and reacted at 150 ° C. for 5 hours. After the reaction, the mixture was cooled to 80 ° C, discharged into 500 ml of methanol, filtered, washed, recrystallized with pyridine and dried to obtain the compound represented by the following formula (A). Elemental analysis value C H N Cl measured value 65.53% 3.34% 7.87% 19.55% calculated value 64.24% 3.40% 7.89% 19.96% of the compound 39g (yield 63%) was obtained. λmax (chloroform) = 745 nm. The transmittance in chloroform is 5% at 700 nm, 49% at 600 nm, 73% at 550 nm, and 500 nm.
It was 82%, 84% at 480 nm, and 42% at 400 nm.
式（Ａ）の色素を減圧下、多孔質アルミナ薄膜を表面に
有するガラス基材に加熱昇華、蒸着させた。このように
して製造した緑色フィルターは耐侯性に優れ、かつ分光
特性が優れていた。The dye of formula (A) was heated and sublimed and evaporated under reduced pressure on a glass substrate having a porous alumina thin film on its surface. The green filter manufactured in this manner had excellent weather resistance and spectral characteristics.
実施例２ ロイコ−1,4,5,8−テトラヒドロキシアントラキノン24
g、ｐ−クロロアニリン90g、アニリン66g、ホウ酸5g、3
5％塩酸10gと、亜鉛2gを混合し、150℃で５時間反応さ
せた。反応後80℃に冷却し、メタノール500mlに排出
し、濾過、洗浄、ピリジンで再結晶した後乾燥し、下式
（Ｂ） 元素分析値 Ｃ Ｈ Ｎ C1 実測値 76.68％ 4.39％ 9.14％ 5.78％ 計算値 75.18％ 4.48％ 9.23％ 5.84％ の化合物42g（収率79％）を得た。λmax（クロロホル
ム）＝752nmであった。Example 2 Leuco-1,4,5,8-tetrahydroxyanthraquinone 24
g, 90 g of p-chloroaniline, 66 g of aniline, 5 g of boric acid, 3
10% of 5% hydrochloric acid and 2 g of zinc were mixed and reacted at 150 ° C. for 5 hours. After the reaction, the mixture was cooled to 80 ° C, discharged into 500 ml of methanol, filtered, washed, recrystallized with pyridine, and dried to obtain the following formula (B). Elemental analysis value C H N C 1 actual value 76.68% 4.39% 9.14% 5.78% calculated value 75.18% 4.48% 9.23% 5.84% of the compound 42g (yield 79%) was obtained. λmax (chloroform) = 752 nm.
式（Ｂ）の色素を、エチレングリコールに溶解し、150
℃にてポリエステルフィルムを浸漬し、１時間染色し
た。このポリエステルフィルムは緑色になり、カラーフ
ィルターとしての分光特性に優れていた。Dissolve the dye of formula (B) in ethylene glycol to give 150
The polyester film was dipped at ℃ and dyed for 1 hour. This polyester film turned green and had excellent spectral characteristics as a color filter.
実施例３ ロイコ−1,4,5,8−テトラヒドロキシアントラキノン24
g、ｐ−クロロアニリン90g、ｐ−トルイジン76g、ホウ
酸5g、35％塩酸10gと、亜鉛2gを混合し、150℃で５時間
反応させた。反応後80℃に冷却し、メタノール500mlに
排出し、濾過、洗浄、ピリジンで再結晶した後乾燥し、
下式（Ｃ） 元素分析値 Ｃ Ｈ Ｎ Cl 実測値 77.37％ 5.02％ 8.54％ 5.41％ 計算値 75.86％ 5.12％ 8.63％ 5.46％ の化合物41g（収率72％）を得た。λmax（クロロホル
ム）＝753nmであった。Example 3 Leuco-1,4,5,8-tetrahydroxyanthraquinone 24
g, 90 g of p-chloroaniline, 76 g of p-toluidine, 5 g of boric acid, 10 g of 35% hydrochloric acid and 2 g of zinc were mixed and reacted at 150 ° C. for 5 hours. After the reaction, the mixture was cooled to 80 ° C., discharged into 500 ml of methanol, filtered, washed, recrystallized with pyridine and dried,
The following formula (C) Elemental analysis value C H N Cl actual value 77.37% 5.02% 8.54% 5.41% Calculated value 75.86% 5.12% 8.63% 5.46% of the compound 41 g (yield 72%) was obtained. λmax (chloroform) = 753 nm.
式（Ｃ）の色素を、エチレングリコールに溶解し、150
℃にてポリエステルフィルムを浸漬し、１時間染色し
た。このポリエステルフィルムは緑色になり、カラーフ
ィルターとしての分光特性に優れていた。The dye of formula (C) is dissolved in ethylene glycol to give 150
The polyester film was dipped at ℃ and dyed for 1 hour. This polyester film turned green and had excellent spectral characteristics as a color filter.
実施例４ ロイコ−1,4,5,8−テトラヒドロキシアントラキノン24
g、ｐ−クロロアニリン90g、ｐ−ｎ−ブチルアリニン10
5g、ホウ酸5g、35％塩酸10gと、亜鉛2gを混合し、150℃
で５時間反応させた。反応後80℃に冷却し、メタノール
500mlに排出し、濾過、洗浄、ピリジンで再結晶した後
乾燥し、下式（Ｄ） 元素分析値 Ｃ Ｈ Ｎ Cl 実測値 79.00％ 6.50％ 7.15％ 4.53％ 計算値 77.45％ 6.63％ 7.23％ 4.57％ の化合物42g（収率62％）を得た。λmax（クロロホル
ム）＝754nmであった。Example 4 Leuco-1,4,5,8-tetrahydroxyanthraquinone 24
g, p-chloroaniline 90 g, pn-butylalinine 10
Mix 5g, 5g boric acid, 10g 35% hydrochloric acid and 2g zinc, 150 ℃
And reacted for 5 hours. After reaction, cool to 80 ℃ and methanol.
Discharge to 500 ml, filter, wash, recrystallize with pyridine and dry, then use the formula (D) Elemental analysis value C H N Cl actual value 79.00% 6.50% 7.15% 4.53% Calculated value 77.45% 6.63% 7.23% 4.57% 42 g of the compound (yield 62%) was obtained. λmax (chloroform) = 754 nm.
式（Ｄ）の色素を、エチレングリコールに溶解し、150
℃にてポリエステルフィルムを浸漬し、１時間染色し
た。このポリエステルフィルムは緑色になり、カラーフ
ィルターとしての分光特性に優れていた。The dye of formula (D) is dissolved in ethylene glycol to give 150
The polyester film was dipped at ℃ and dyed for 1 hour. This polyester film turned green and had excellent spectral characteristics as a color filter.
本発明のアントラキノン系長波長吸収色素を用いたカラ
ーフィルターは緑色を呈し、分光特性において優れてお
り、実用上価値ある色素である。The color filter using the anthraquinone-based long-wavelength absorbing dye of the present invention exhibits a green color and is excellent in spectral characteristics, and is a dye of practical value.
Claims (2)
つ以上がハロゲン原子で置換され、残りのベンゼン核は
それぞれ同一または独立に、低級アルキル基で置換され
ていてもよい。〕 で示されるアントラキノン系長波長吸収色素。1. A general formula (I) [In the formula, at least one or more of the benzene nuclei A, B, C, and D may be substituted with a halogen atom, and the remaining benzene nuclei may be identically or independently substituted with a lower alkyl group. ] The anthraquinone long wavelength absorption dye shown by these.
とする特許請求の範囲第１項に記載の色素。2. The dye according to claim 1, which is used for a color filter.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60132036A JPH0742411B2 (en) | 1985-06-19 | 1985-06-19 | Anthraquinone long-wavelength absorption dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60132036A JPH0742411B2 (en) | 1985-06-19 | 1985-06-19 | Anthraquinone long-wavelength absorption dye |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4158005A Division JPH0745263B2 (en) | 1992-06-17 | 1992-06-17 | Laser optical recording medium using anthraquinone-based long wavelength absorbing dye |
| JP26951194A Division JP2569285B2 (en) | 1994-11-02 | 1994-11-02 | Anthraquinone long wavelength absorbing dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61291651A JPS61291651A (en) | 1986-12-22 |
| JPH0742411B2 true JPH0742411B2 (en) | 1995-05-10 |
Family
ID=15072001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60132036A Expired - Fee Related JPH0742411B2 (en) | 1985-06-19 | 1985-06-19 | Anthraquinone long-wavelength absorption dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0742411B2 (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2590109B2 (en) * | 1987-07-03 | 1997-03-12 | 三井東圧化学株式会社 | Sulfur-containing urethane resin for near infrared absorption |
| JPH01129068A (en) * | 1987-11-13 | 1989-05-22 | Mitsui Toatsu Chem Inc | High-purity anthraquinone pigment for near-infrared filter |
| JPH0813930B2 (en) * | 1987-12-28 | 1996-02-14 | 三井東圧化学株式会社 | High-purity anthraquinone dye for near infrared absorption filters |
| JPH0730300B2 (en) * | 1988-04-01 | 1995-04-05 | 三井東圧化学株式会社 | Alkyl phthalocyanine near infrared absorber and display / recording material using the same |
| JP2569285B2 (en) * | 1994-11-02 | 1997-01-08 | 三井東圧化学株式会社 | Anthraquinone long wavelength absorbing dye |
| JP2002274087A (en) * | 2001-03-15 | 2002-09-25 | Dainippon Printing Co Ltd | Transparent card |
| US6811575B2 (en) * | 2001-12-20 | 2004-11-02 | Rohm And Haas Company | Method for marking hydrocarbons with anthraquinones |
| JPWO2006006527A1 (en) | 2004-07-12 | 2008-04-24 | 大日本印刷株式会社 | Electromagnetic shield filter |
| EP4188906A1 (en) * | 2020-07-29 | 2023-06-07 | Dow Global Technologies LLC | Aromatic hydrocarbon-soluble anthraquinone |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62903A (en) * | 1985-06-05 | 1987-01-06 | Sumitomo Chem Co Ltd | Near infrared ray absorbing filter |
-
1985
- 1985-06-19 JP JP60132036A patent/JPH0742411B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61291651A (en) | 1986-12-22 |
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