KR100398084B1 - New azo metal complex, and use thereof - Google Patents
New azo metal complex, and use thereof Download PDFInfo
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Abstract
본 발명은 다음 화학식 1의 아조계 염료를 여러 가지 금속이온과 반응시켜 얻어진 신규 구조의 다음 화학식 2의 아조계 금속 착화합물과 이 화합물들의 응용에 관한 것이다.The present invention relates to the azo-based metal complex of the following Chemical Formula 2 and its application of a novel structure obtained by reacting an azo dye of the following Chemical Formula 1 with various metal ions.
상기 화학식 1과 2에서, X, R1, R2, R3및 M은 각각 발명의 상세한 설명에서 정의한 바와 같다.In Chemical Formulas 1 and 2, X, R 1 , R 2 , R 3 and M are as defined in the detailed description of the invention, respectively.
Description
본 발명에서는 제조 단가가 적고 합성하기 쉬운 다음 화학식 2의 아조계 금속 착화합물을 제조하여 이를 광기록 매체에 응용한다.In the present invention, the azo-based metal complex of the following formula (2) is prepared and applied to an optical recording medium having a low manufacturing cost and easy to synthesize.
[화학식 2][Formula 2]
상기 화학식 2에서, X는 벤젠 고리, 나프탈렌 고리 또는 안트라센 고리이고, R1, R2및 R3은 각각 수소 원자, 카르복실산기(-COOH), 메톡시기(-OCH3), 알킬기(-(CH2)nCH3, n=0∼5), 나이트로기(-NO2), 하이드록시기(-OH), 할로겐 원자, 페닐기, 시아노기(-CN) 또는 술폰산기(-SO3H)이고, M은 금속이온으로 Ni, Zn, Co, Cu, Fc,Pt, Pb, 또는 Ag를 포함한다.In Formula 2, X is a benzene ring, a naphthalene ring or an anthracene ring, R 1 , R 2 and R 3 are each a hydrogen atom, a carboxylic acid group (-COOH), a methoxy group (-OCH 3 ), an alkyl group (-( CH 2 ) n CH 3 , n = 0 to 5), nitro group (-NO 2 ), hydroxy group (-OH), halogen atom, phenyl group, cyano group (-CN) or sulfonic acid group (-SO 3 H ), M is a metal ion and includes Ni, Zn, Co, Cu, Fc, Pt, Pb, or Ag.
본 발명은 신규 구조의 아조계 염료와 이의 금속 착화합물, 그리고 이들 화합물을 광기록 물질로서 이용하는 광기록 매체에 관한 것이다. 이러한 광기록 매체는 기능에 따라 기록되어진 정보를 재생만 하는 재생전용형(Read Only Memory)과 1회에 한하여 기록이 가능한 추기형(Write Only Read Many: WORM) 및 기록 후 소거 및 재기록이 가능한 소거가능형(Erasable)으로 구분된다. 기록 가능한 광기록 매체는 기록 전후 기록층의 물리적인 변형, 상 변화, 자기적 성질의 변화 등에 기인한 반사율 변화로 기록 재생하게 된다. 상기 추기형 광기록 매체로는 CD-R(Compact Disk Recordable)이 가장 널리 알려져 있다. 이러한 광기록 매체의 특성을 향상시키면서 제조를 용이하게 하기 위하여 여러 가지 광기록 물질들이 제안되어 일부 실용화되고 있다. 상기 CD-R용 광기록 물질로는 시아닌 염료(일본특허공개 소58-125246), 프탈로시아닌 염료(유럽특허 제676751호), 아조 염료(미국특허 제5,441,844호), 이중염 염료(double salt)(미국특허 제4,626,490호) 등이 공지되어 있다.The present invention relates to an azo dye having a novel structure, a metal complex compound thereof, and an optical recording medium using these compounds as an optical recording material. Such optical recording media include a read only memory for reproducing recorded information according to a function, a write once read many (WORM) for recording only once, and an erase for rewriting and rewriting after recording. It is classified as Erasable. The recordable optical recording medium records and reproduces by reflectance change due to physical deformation, phase change, magnetic property change, and the like before and after recording. CD-R (Compact Disk Recordable) is the most widely known recordable optical recording medium. In order to improve the characteristics of the optical recording medium and to facilitate the manufacture of various optical recording materials have been proposed and some practical use. Examples of the optical recording material for CD-R include cyanine dye (Japanese Patent Laid-Open No. 58-125246), phthalocyanine dye (European Patent No. 667751), azo dye (US Pat. No. 5,441,844), double salt ( U.S. Patent No. 4,626,490) and the like are known.
최근, 정보량이 점차 증가함에 따라, 저장 정보의 용량을 증가시킨 DVD-R(Digital Versatile Disk Recordable)이 제안되었다. 이 DVD-R은 광원으로서 630 내지 670 nm 파장 영역의 적색 다이오드 레이저를 채용하고 비트 크기 및 트랙 간격을 감소시킴으로써 CD-R의 경우와 비교하여 기억 용량을 6 내지 8배로 증가시켜 기록 밀도를 향상시켰다. DVD-R용 광기록 물질로 사용되기 위해서는 기록 파장에서의 높은 굴절율과 적절한 흡수 특성, 유기용매에서의 뛰어난 용해도, 기록부위의 균일성 및 안정성뿐만 아니라, 합성이 용이하고 재료원가가 저렴해야 한다는 특성 등이 요구된다. DVD-R용 광기록 물질의 예로는 시아닌 염료, 등이 있다. 그러나 기존 염료 물질들의 경우, 프탈로시아닌 염료는 합성하기가 어렵고 제조 단가가 높다는 단점이 있고 시아닌 염료는 광이나 열에 약하다. 이처럼 기존 염료는 상술한 특성 측면에서 아직도 개선의 여지가 많다.In recent years, as the amount of information gradually increases, a digital versatile disk recordable (DVD-R) has been proposed that increases the capacity of stored information. The DVD-R employs a red diode laser in the 630-670 nm wavelength range as a light source and reduces the bit size and track spacing to increase the recording capacity by 6 to 8 times compared to the case of CD-R to improve recording density. . To be used as an optical recording material for DVD-R, high refractive index and proper absorption characteristics at recording wavelengths, excellent solubility in organic solvents, uniformity and stability of recording sites, as well as easy synthesis and low material cost Etc. are required. Examples of the optical recording material for DVD-R include cyanine dyes, and the like. However, in the case of existing dye materials, phthalocyanine dyes are difficult to synthesize and have a high manufacturing cost, and cyanine dyes are weak to light or heat. As such, the existing dyes still have much room for improvement in view of the above-described properties.
본 발명이 이루고자 하는 기술적 과제는 합성하기가 기존의 프탈로시아닌이나 시아닌에 비해 비교적 용이하고, 제조 수율이 높으며, 광적, 열적으로 우수한 특성을 보이는 새로운 아조계 금속 착화합물과, 이를 광기록 물질로 하는 광기록 매체를 제공하는 것이다.The technical problem to be achieved by the present invention is a new azo-based metal complex compound which is relatively easy to synthesize compared to existing phthalocyanine or cyanine, has a high production yield, and has excellent optical and thermal properties, and an optical recording using the same as an optical recording material. To provide a medium.
상기 기술적 과제를 이루기 위하여 본 발명에서는 첫째, 다음 화학식 1로 표시되는 아조계 염료를 제조한다.In order to achieve the above technical problem, the present invention firstly prepares an azo dye represented by the following Chemical Formula 1.
[합성예 1]Synthesis Example 1
화합물 A로 표시되는 아조계 염료를 제조하는 방법은 다음과 같다.The method for producing the azo dye represented by compound A is as follows.
상기 화학식 3으로 표시되는 아미노벤조산 2.74 g(0.02 mol)을 0 ℃에서 황산 17 mL에 녹인 후 온도를 -20 ℃ 까지 냉각시킨다. 3.8 g의 HO3SONO 을 위의 용액에 천천히 가한 후, 2 시간 동안 교반한다. 노랑색 고체가 생성되면, 화학적 4로 표시되는 다이에틸아미노페놀 3.30 g(0.02 mol)을 상기 교반물에 가하여 커플링 시킨다. 20∼30 분간 교반 한 후, 얼음물 10 mL를 가한다. 이 용액을30 분간 교반한 후, 이 혼합물을 pH 6으로 중화한다. 붉은 갈색의 고체가 생성되면 흡인여과하고 알콜류를 사용하여 재침전 시킨 후 40∼60℃ 에서 진공 건조시켜 제조한다. 상기 A 색소 0.3 g을 테트라플루오로프로판올 10 mL에 용해한 다음, 이를 기판상에 스핀코팅하여 색소층을 형성하였다.2.74 g (0.02 mol) of aminobenzoic acid represented by Chemical Formula 3 was dissolved in 17 mL of sulfuric acid at 0 ° C., and then cooled to −20 ° C. 3.8 g of HO 3 SONO is slowly added to the above solution and then stirred for 2 hours. When a yellow solid is formed, 3.30 g (0.02 mol) of diethylaminophenol represented by Chemical Formula 4 is added to the stirring to couple. After stirring for 20-30 minutes, 10 mL of ice water is added. After stirring this solution for 30 minutes, the mixture is neutralized to pH 6. When a reddish brown solid is produced, the resultant is filtered by suction, reprecipitated with alcohols, and then vacuum dried at 40 to 60 ° C. 0.3 g of the A pigment was dissolved in 10 mL of tetrafluoropropanol, and then spin coated onto a substrate to form a dye layer.
이어서 제조된 박막의 흡수스펙트럼은 UV-VIS 스펙트로포토미터 (Scinco사, S-2100/2000)를 사용하여 조사하였다. 그 결과, A 색소의 최대흡수파장(λmax)은 427 nm로 나타났다.1H NMR (Varian, 400 MHz): CDCl3,ppm, δ1.17(t, 3H), δ3.35∼ 3.59(m, 2H), δ5.98(s, 1H), δ6.4 (d, 1H), δ7.4(d, 1H), δ7.85(d, 1H), δ8.15 (d, 1H)Subsequently, the absorption spectrum of the prepared thin film was investigated using a UV-VIS spectrophotometer (Scinco, S-2100 / 2000). As a result, the maximum absorption wavelength (λ max ) of the A pigment was 427 nm. 1 H NMR (Varian, 400 MHz): CDCl 3, ppm, δ 1.17 (t, 3H), δ 3.35-3.59 (m, 2H), δ 5.98 (s, 1H), δ6.4 (d, 1H), δ 7.4 (d, 1H), δ 7.85 (d, 1H), δ8.15 (d, 1H)
[합성예 2]Synthesis Example 2
화합물 B로 표시되는 아조계 염료를 제조하는 방법은 다음과 같다.The method for producing the azo dye represented by the compound B is as follows.
상기 화학식 5로 표시되는 아미노아세토페논 1.0 g(0.007 mol)을 0 ℃ 에서 황산 17mL에 녹인 후 온도를 -20 ℃ 까지 냉각시킨다. 소량의 물에 아질산나트륨 0.56 g(0.008 mol)을 녹인 용액을 천천히 가하고 20∼30 분간 교반시킨다. 노랑색 고체가 생성되면 얼음을 20 g 을 넣고 10 분간 교반한 후, 화학식 4로 표시되는 다이에틸아미노페놀 1.22 g(0.007 mol)을 메탄올 20 mL에 녹인 용액을 천천히가하고 2 시간 커플링시킨다. 이 혼합물을 pH 5∼6으로 중화한다. 붉은 갈색의 고체가 생성되면 흡인여과하고 알코올류를 사용하여 재침전시킨 후 40∼60 ℃ 에서 진공 건조시켜 제조한다. 상기 B 색소 0.3 g을 테트라플루오로프로판올 10 mL에 용해한 다음, 이를 기판상에 스핀코팅하여 색소층을 형성하였다. 이어서 제조된 박막의 흡수스펙트럼은 UV-VIS 스펙트로포토미터를 이용하여 조사하였다. 그 결과, B 색소의 최대흡수파장(λmax)은 510 nm로 나타났다.1H NMR : CDCl3, ppm, 1.24(t, 3H), δ3.35∼3.59(m, 2H), δ5.98(s, 1H), δ6.48(d, 1H), δ7.35(d, 1H), δ7.69(d, 1H), δ8.0(d, 1H).1.0 g (0.007 mol) of aminoacetophenone represented by Chemical Formula 5 was dissolved in 17 mL of sulfuric acid at 0 ° C., and then cooled to −20 ° C. A solution of 0.56 g (0.008 mol) of sodium nitrite is slowly added to a small amount of water and stirred for 20 to 30 minutes. When a yellow solid is formed, 20 g of ice is added and stirred for 10 minutes. Then, a solution of 1.22 g (0.007 mol) of diethylaminophenol represented by Formula 4 in 20 mL of methanol is slowly added thereto and then coupled for 2 hours. The mixture is neutralized to pH 5-6. When a reddish brown solid is produced, the resultant is filtered by suction, reprecipitated with alcohol, and then vacuum dried at 40 to 60 ° C. 0.3 g of the B pigment was dissolved in 10 mL of tetrafluoropropanol, and then spin coated onto a substrate to form a dye layer. Subsequently, the absorption spectrum of the prepared thin film was examined using a UV-VIS spectrophotometer. As a result, the maximum absorption wavelength (λ max ) of the B pigment was found to be 510 nm. 1 H NMR: CDCl 3 , ppm, 1.24 (t, 3H), δ 3.35-3.59 (m, 2H), δ 5.98 (s, 1H), δ6.48 (d, 1H), δ7.35 (d , 1H), δ 7.69 (d, 1H), δ 8.0 (d, 1H).
[합성예 3]Synthesis Example 3
화합물 C로 표시되는 아조계 염료를 제조하는 방법은 다음과 같다.The method for producing the azo dye represented by the compound C is as follows.
상기 화학식 6으로 표시되는 디아조나프톨술포닉산 2.9 g(0.01 mol)을 0 ℃ 에서 황산 8.82 g에 녹인 후 온도를 -20 ℃ 까지 냉각시킨다. 소량의 물에 아질산나트륨 0.83 g(0.012 mol)을 녹인 용액을 천천히 가하고 20∼30 분간 교반시킨다. 노랑색 고체가 생성되면, 화학식 4로 표시되는 다이에틸아미노페놀 1.65 g(0.01 mol)을 메탄올에 녹인 후 상기 교반물에 가하여 커플링 시킨다. 20∼30분간 교반한 후, 얼음물 10 mL를 가한다. 이 용액을 30 분간 교반한 후, 이 혼합물을 pH 7으로 중화한다. 붉은 갈색의 고체가 생성되면 흡인여과하고 알콜류를 사용하여 재침전시킨 후 40∼60 ℃에서 진공 건조시켜 제조한다. 상기 C 색소 0.3 g을 테트라플루오로프로판올 10 mL에 용해한 다음, 이를 기판상에 스핀코팅하여 색소층을 형성하였다. 이어서 제조된 박막의 흡수스펙트럼은 UV-VIS 스펙트로포토미터를 사용하여 조사하였다. 그 결과, C 색소의 최대흡수파장(λmax)은 526 nm로 나타났다.1H NMR: D2O, ppm, δ0.65(t, 3H), δ3.36∼3.37(m, 2H), δ5.2(s, 1H), δ5.55(s, 1H), δ6.4(d, 1H), δ6.95(d, 1H), δ7.15(d, 1H), δ7.25(d, 1H), δ7.42(d, 1H), δ8.56(s, 1H)After dissolving 2.9 g (0.01 mol) of diazonaphthol sulfonic acid represented by Chemical Formula 6 at 8.82 g of sulfuric acid at 0 ° C., the temperature is cooled to −20 ° C. Slowly add a solution of 0.83 g (0.012 mol) of sodium nitrite to a small amount of water and stir for 20 to 30 minutes. When a yellow solid is formed, 1.65 g (0.01 mol) of diethylaminophenol represented by Chemical Formula 4 is dissolved in methanol, and then added to the stirred solution to be coupled. After stirring for 20-30 minutes, 10 mL of ice water is added. After the solution is stirred for 30 minutes, the mixture is neutralized to pH 7. When a reddish brown solid is produced, the resultant is filtered by suction, reprecipitated using alcohols, and then vacuum dried at 40 to 60 ° C. 0.3 g of the C dye was dissolved in 10 mL of tetrafluoropropanol, and then spin coated onto a substrate to form a dye layer. Subsequently, the absorption spectrum of the prepared thin film was investigated using a UV-VIS spectrophotometer. As a result, the maximum absorption wavelength (λ max ) of the C dye was found to be 526 nm. 1 H NMR: D 2 O, ppm, δ 0.65 (t, 3H), δ 3.36-3.37 (m, 2H), δ5.2 (s, 1H), δ5.55 (s, 1H), δ6. 4 (d, 1H), δ 6.95 (d, 1H), δ 7.15 (d, 1H), δ 7.25 (d, 1H), δ 7.42 (d, 1H), δ 8.56 (s, 1H )
상기 기술적 과제를 이루기 위하여 본 발명에서는 두 번째로, 상기 화학식 2로 표시되는 아조계 금속 착화합물을 제조한다.In order to achieve the above technical problem, in the present invention, an azo-based metal complex represented by Chemical Formula 2 is prepared.
[합성예 4]Synthesis Example 4
화합물 A1으로 표시되는 아조의 니켈 착화합물을 제조하는 방법은 다음과 같다.The method for producing the nickel complex of azo represented by compound A1 is as follows.
상기 화학식 7로 표시되는 아조는 합성예 1에서 제조한 화합물 A이다. 제조한 화학식 7의 아조 0.5 g을 메탄올 10 mL에 녹인 후, 메탄올 0.9 mL에 0.07 g의 니켈아세테이트 4수화물을 녹인 용액을 천천히 가한다. 3시간 동안 교반을 시킨 후 20 mL의 물을 첨가한다. 고체가 생성되면 흡인여과하고 60∼80 ℃에서 진공 건조시켜 제조한다. 상기 A1 색소 0.3 g을 테트라플루오로프로판올 10 mL에 용해한 다음, 이를 기판상에 스핀코팅하여 색소층을 형성하였다. 이어서 제조된 박막의 흡수스펙트럼은 UN-VIS 스펙트로포토미터를 사용하여 조사하였다. 그 결과, A1 색소의 최대흡수파장(λmax)은 476 nm로 나타났다.Azo represented by Formula 7 is Compound A prepared in Synthesis Example 1. After dissolving 0.5 g of the azo compound of Formula 7 in 10 mL of methanol, a solution of 0.07 g of nickel acetate tetrahydrate in 0.9 mL of methanol was slowly added. After stirring for 3 hours, 20 mL of water is added. When a solid is produced, it is produced by suction filtration and vacuum drying at 60 to 80 캜. 0.3 g of the A1 dye was dissolved in 10 mL of tetrafluoropropanol, and then spin coated onto a substrate to form a dye layer. Subsequently, the absorption spectrum of the prepared thin film was investigated using a UN-VIS spectrophotometer. As a result, the maximum absorption wavelength (λ max ) of the A1 dye was found to be 476 nm.
[합성예 5]Synthesis Example 5
화합물 A2으로 표시되는 아조의 코발트 착화합물을 제조하는 방법은 상기 합성예 4와 동일하다. 단지 니켈아세테이트 4수화물 대신 질산코발트 6수화물을사용한다. A2 색소의 최대흡수파장(λmax)은 490 nm로 나타났다.The method for producing the cobalt complex compound of azo represented by compound A2 is the same as in Synthesis Example 4. Use cobalt nitrate hexahydrate instead of nickel acetate tetrahydrate. The maximum absorption wavelength (λ max ) of the A2 dye was found to be 490 nm.
[합성예 6]Synthesis Example 6
화합물 A3으로 표시되는 아조의 아연 착화합물을 제조하는 방법은 상기 합성예 4와 동일하다. 단지 니켈아세테이트 4수화물 대신 질산코발트 6수화물을 사용한다. A3 색소의 최대흡수파장(λmax)은 486 nm로 나타났다.The method for producing the zinc complex of azo represented by the compound A3 is the same as in Synthesis Example 4. Use cobalt nitrate hexahydrate instead of nickel acetate tetrahydrate. The maximum absorption wavelength (λ max ) of the A3 dye was found to be 486 nm.
[합성예 7]Synthesis Example 7
화합물 A4으로 표시되는 아조의 구리 착화합물을 제조하는 방법은 상기 합성예 4와 동일하다. 단지 니켈아세테이트 4수화물 대신 질산구리 수화물을 사용한다. A4 색소의 최대흡수파장(λmax)은 590 nm로 나타났다.The method for producing the copper complex of azo represented by compound A4 is the same as in Synthesis Example 4. Use copper nitrate hydrate instead of nickel acetate tetrahydrate. The maximum absorption wavelength (λ max ) of the A4 dye was found to be 590 nm.
[합성예 8]Synthesis Example 8
화합물 B1으로 표시되는 아조의 니켈 착화합물을 제조하는 방법은 다음과 같다.The method for producing the nickel complex of azo represented by compound B1 is as follows.
상기 화학식 8로 표시되는 아조는 상기 합성예 2에서 제조한 화합물 B이다.제조한 화학식 8의 아조 0.2 g을 메탄올 4.5 mL에 녹인 후, 메탄올 0.9 mL에 0.07 g의 니켈아세테이트 4수화물을 녹인 용액을 천천히 가한다. 3시간 동안 교반을 시킨후 20 mL의 물을 첨가한다. 고체가 생성되면 흡인여과하고 6O∼80 ℃에서 진공 건조시켜 제조한다. 상기 B1 색소 0.3 g을 테트라플루오로프로판올 10 mL에 용해한 다음, 이를 기판상에 스핀코팅하여 색소층을 형성하였다. 이어서 제조된 박막의 흡수스펙트럼은 UV-VIS 스펙트로포토미터를 사용하여 조사하였다. 그 결과, B1 색소의 최대흡수파장(λmax)은 538 nm로 나타났다.Azo represented by Chemical Formula 8 is Compound B prepared in Synthesis Example 2. 0.2 g of azo prepared in Chemical Formula 8 was dissolved in 4.5 mL of methanol, and then 0.07 g of nickel acetate tetrahydrate was dissolved in 0.9 mL of methanol. Apply slowly After stirring for 3 hours, 20 mL of water are added. When a solid is produced, it is produced by suction filtration and vacuum drying at 60-80 ° C. 0.3 g of the B1 dye was dissolved in 10 mL of tetrafluoropropanol, and then spin coated onto a substrate to form a dye layer. Subsequently, the absorption spectrum of the prepared thin film was investigated using a UV-VIS spectrophotometer. As a result, the maximum absorption wavelength (λ max ) of the B1 dye was found to be 538 nm.
[합성예 9]Synthesis Example 9
화합물 B2으로 표시되는 아조의 코발트 착화합물을 제조하는 방법은 상기 합성예 8과 동일하다. 단지 니켈아세테이트 4수화물 대신 질산코발트 6수화물을 사용한다. B2 색소의 최대흡수파장(λmax)은 550 nm로 나타났다.The method for producing the cobalt complex compound of azo represented by compound B2 was the same as in Synthesis Example 8. Use cobalt nitrate hexahydrate instead of nickel acetate tetrahydrate. The maximum absorption wavelength (λ max ) of the B2 pigment was found to be 550 nm.
[합성예 10]Synthesis Example 10
화합물 B3으로 표시되는 아조의 아연 착화합물을 제조하는 방법은 상기 합성예 8과 동일하다. 단지 니켈아세테이트 4수화물 대신 질산코발트 6수화물을 사용한다. B3 색소의 최대흡수파장(λmax)은 542 nm로 나타났다.The method for producing the zinc complex of azo represented by the compound B3 was the same as in Synthesis Example 8. Use cobalt nitrate hexahydrate instead of nickel acetate tetrahydrate. The maximum absorption wavelength (λ max ) of the B3 dye was found to be 542 nm.
[합성예 11]Synthesis Example 11
화합물 B4으로 표시되는 아조의 구리 착화합물을 제조하는 방법은 상기 합성예 8과 동일하다. 단지 니켈아세테이트 4수화물 대신 질산구리 x수화물을 사용한다. B4 색소의 최대흡수파장(λmax)은 542 nm로 나타났다.The method for producing the azo copper complex represented by compound B4 is the same as in Synthesis Example 8. Use copper nitrate xhydrate instead of nickel acetate tetrahydrate. The maximum absorption wavelength (λ max ) of the B4 dye was found to be 542 nm.
[합성예 12]Synthesis Example 12
화화물 C1으로 표시되는 아조의 니켈 착화합물을 제조하는 방법은 다음과 같다.The method for producing the azo nickel complex represented by the sulfide C1 is as follows.
상기 화학식 9로 표시되는 아조는 상기 합성예 3에서 제조한 화합물 C이다. 제조한 화학식 9의 아조 1.1 g을 메탄올 15 mL에 녹인 후, 메탄올 4 mL에 1.49 g의 니켈아세테이트 4수화물을 녹인 용액을 천천히 가한다. 3시간 동안 교반 시킨 후 20 mL의 물을 첨가한다. 고체가 생성되면 흡인여과하고 60∼80 ℃에서 진공 건조시켜 제조한다. 상기 C1 색소 0.3 g을 테트라플루오로프로판올 10 mL에 용해한 다음, 이를 기판상에 스핀코팅하여 색소층을 형성하였다. 이어서 제조된 박막의 흡수스펙트럼은 UN-VIS 스펙트로포토미터를 사용하여 조사하였다. 그 결과, C1 색소의 최대흡수파장(λmax)은 545 nm로 나타났다.Azo represented by the formula (9) is compound C prepared in Synthesis Example 3. After dissolving 1.1 g of the azo compound of Formula 9 in 15 mL of methanol, a solution of 1.49 g of nickel acetate tetrahydrate in 4 mL of methanol was slowly added. After stirring for 3 hours, 20 mL of water is added. When a solid is produced, it is produced by suction filtration and vacuum drying at 60 to 80 캜. 0.3 g of the C1 dye was dissolved in 10 mL of tetrafluoropropanol, and then spin coated onto a substrate to form a dye layer. Subsequently, the absorption spectrum of the prepared thin film was investigated using a UN-VIS spectrophotometer. As a result, the maximum absorption wavelength (λ max ) of the C1 dye was found to be 545 nm.
[합성예 13]Synthesis Example 13
화합물 C2으로 표시되는 아조의 코발트 착화합물을 제조하는 방법은 상기 합성예 12와 동일하다. 단지 니켈아세테이트 4수화물 대신 질산코발트 6수화물을 사용한다. C2 색소의 최대흡수파장(λmax)은 560 nm로 나타났다.The method for producing the cobalt complex compound of azo represented by the compound C2 was the same as in Synthesis Example 12. Use cobalt nitrate hexahydrate instead of nickel acetate tetrahydrate. The maximum absorption wavelength (λ max ) of the C2 dye was found to be 560 nm.
[합성예 14]Synthesis Example 14
화합물 C3으로 표시되는 아조의 아연 착화합물을 제조하는 방법은 상기 합성예 12와 동일하다. 단지 니켈아세테이트 4수화물 대신 질산아연 6수화물을 사용한다. C3 색소의 최대흡수파장(λmax)은 550 nm로 나타났다.The method for producing the zinc complex of azo represented by the compound C3 is the same as in Synthesis Example 12. Use zinc nitrate hexahydrate instead of nickel acetate tetrahydrate. The maximum absorption wavelength (λ max ) of the C3 dye was found to be 550 nm.
[합성예 15]Synthesis Example 15
화합물 B4으로 표시되는 아조의 구리 착화합물을 제조하는 방법은 상기 합성예 12와 동일하다. 단지 니켈아세테이트 4수화물 대신 질산구리 x수화물을 사용한다. B4 색소의 최대흡수파장(λmax)은 544 nm로 나타났다.The method for producing the copper complex of azo represented by compound B4 is the same as in Synthesis Example 12. Use copper nitrate xhydrate instead of nickel acetate tetrahydrate. The maximum absorption wavelength (λ max ) of the B4 dye was 544 nm.
이상에서 살펴본 바와 같이, 상기 화학식 1로 표시되는 아조계 염료는 합성하기가 용이할 뿐만 아니라 합성 수율이 우수하다. 그리고 상기 화학식 2로 표시되는 아조계 금속 착화합물 또한 합성이 용이하다. 따라서 상기한 화학식 1로 표시되는 아조계 염료와 상기 화학식 2로 표시되는 아조계 금속 착화합물을 광기록 물질로 이용하면 종래의 광기록 물질을 이용한 경우와 비교하여 광기록 물질의 제조단가 등의 측면에서 유리하다.As described above, the azo dye represented by Chemical Formula 1 is not only easy to synthesize, but also has excellent synthesis yield. In addition, the azo-based metal complex represented by Formula 2 is also easy to synthesize. Therefore, when the azo dye represented by Chemical Formula 1 and the azo metal complex compound represented by Chemical Formula 2 are used as the optical recording material, the cost of manufacturing the optical recording material is higher than that of the conventional optical recording material. It is advantageous.
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