KR20150143172A - Method for producing dye master batch - Google Patents

Method for producing dye master batch Download PDF

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KR20150143172A
KR20150143172A KR1020140072352A KR20140072352A KR20150143172A KR 20150143172 A KR20150143172 A KR 20150143172A KR 1020140072352 A KR1020140072352 A KR 1020140072352A KR 20140072352 A KR20140072352 A KR 20140072352A KR 20150143172 A KR20150143172 A KR 20150143172A
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organic solvent
dye
layer
group
formula
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KR1020140072352A
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KR102092333B1 (en
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박일성
김현우
오용호
이종수
최한영
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동우 화인켐 주식회사
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Priority to TW104114877A priority patent/TWI675887B/en
Priority to JP2015097360A priority patent/JP6594027B2/en
Priority to CN201510243152.9A priority patent/CN105315708B/en
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    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0092—Dyes in solid form
    • C09B67/0095—Process features in the making of granulates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • 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
    • C09B57/00—Other synthetic dyes of known constitution
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials

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  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • Optics & Photonics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Mathematical Physics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Optical Filters (AREA)
  • Materials For Photolithography (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The present invention relates to a method for producing a dye master batch. The method for producing a dye master batch of the present invention has advantages capable of reducing a producing time and a producing cost by producing a master batch through a dye extracting operation and a solvent-substitution process without going though a refined dye of powder state in a second step after synthesizing a dye.

Description

염료 마스터 배치의 제조방법 {METHOD FOR PRODUCING DYE MASTER BATCH}METHOD FOR PRODUCING DYE MASTER BATCH [0002]

본 발명은 염료 마스터 배치의 제조방법에 관한 것이다.The present invention relates to a process for preparing a dye masterbatch.

고체 촬상 소자나 액정 표시 소자를 컬러화하기 위하여 소자 위에 형성되는 컬러필터 어레이의 제조방법으로 다양한 방법이 제안되고 있으며, 그 중 색소를 함유하는 착색 감광성 수지 조성물로 이루어진 층을 노광, 현상함으로써 패터닝하는 공정을 필요한 회수만 반복 행하는 컬러 레지스트법이 널리 사용되고 있다.Various methods have been proposed as a method of manufacturing a color filter array formed on a device for coloring solid-state image pickup devices and liquid crystal display devices. In the process of patterning by exposing and developing a layer made of a colored photosensitive resin composition containing a dye Is repeated a necessary number of times is widely used.

컬러 레지스트법에 이용되는 착색 감광성 수지 조성물로서는, 색소로서 안료를 함유하는 것이 널리 보급되어 있다, 그러나, 안료는 입상이며 감광성 수지 조성물에 용해되지 않기 때문에 현상 찌꺼기가 생기는 문제점이 있어, 미세한 패턴의 형성에는 적합하지 않다.As the colored photosensitive resin composition used for the color resist method, it is widely popular that a pigment is contained as a coloring matter. However, since the pigment is granular and does not dissolve in the photosensitive resin composition, there is a problem that a development residue forms, Lt; / RTI >

이에 미세한 패턴의 컬러필터 어레이를 얻을 수 있는 착색 감광성 수지 조성물로서 색소로서 염료를 이용한 감광성 수지 조성물이 제안되고 있으며, 원하는 분광 특성을 구비하고, 박막으로 미세한 착색 패턴을 형성하기 위하여 여러가지 술폰아미드 화합물이 제조되고 있다. 일례로, 대한민국 공개특허 10-2010-0109437호에는 이물질의 발생이 저감된 도포막을 부여하는 조성물에 사용할 수 있는 술폰아미드 화합물의 제조방법을 제공하는 것을 기재하고 있다. 그러나, 상기 제조방법은 염료 합성 후 2회의 결정화와 2회의 세정 및 장시간의 건조를 통하여 정제염료 제조 후, 용제에 용해하는 과정을 통하여 마스터 배치(master batch)를 제조하는 것으로서 2단계 공정(2 step process)로 인하여 장시간의 제조시간과 제조비용이 증가하는 문제점을 가진다.A photosensitive resin composition using a dye as a dye has been proposed as a colored photosensitive resin composition capable of obtaining a fine patterned color filter array. Various photosensitive resin compositions having desired spectroscopic characteristics and various kinds of sulfonamide compounds . For example, Korean Patent Laid-Open No. 10-2010-0109437 discloses a method for producing a sulfonamide compound which can be used in a composition for imparting a coating film with reduced occurrence of foreign matter. However, the above manufacturing method is to prepare a master batch through a process of preparing a purified dye through dissolution in a solvent through crystallization two times after crystallization of the dye, two times of cleaning and drying for a long time, process, which results in an increase in manufacturing time and manufacturing cost over a long period of time.

대한민국 공개특허 제10-2010-0109437호Korean Patent Publication No. 10-2010-0109437

이에, 본 발명은 제조공정을 단순화 시킨 염료 마스터 배치 제조방법을 제공하는 것을 목적으로 한다.Accordingly, it is an object of the present invention to provide a dye masterbatch manufacturing method which simplifies the manufacturing process.

상기 과제를 해결하고자, 본 발명은 염료 전구체로부터 합성된 염료에 물과 유기용매(1)를 가한 후 염료가 용해된 유기용매(1)층만 추출하는 단계; 및 상기 추출된 유기용매(1)층에 유기용매(2)를 가한 후 감압증류하여 유기용매(1)를 제거하는 단계;를 포함하며, 상기 유기용매(2)는 유기용매(1)보다 끓는점이 높은 것인, 염료 마스터 배치를 제조하는 방법을 제공한다.In order to solve the above problems, the present invention provides a method for producing a dye precursor comprising the steps of: adding water and an organic solvent (1) to a dye synthesized from a dye precursor, and then extracting only the organic solvent (1) And removing the organic solvent (1) by distillation under reduced pressure after adding the organic solvent (2) to the extracted organic solvent (1) layer, wherein the organic solvent (2) Is higher than that of the dye masterbatch.

본 발명의 일 구현예는 염료 전구체로부터 합성된 염료를 감압증류하고 물과 유기용매(1)를 가한 후 염료가 용해된 유기용매(1)층만 추출하는 단계; 및 상기 추출된 유기용매(1)층에 유기용매(2)를 가한 후 감압증류하여 유기용매(1)를 제거하는 단계;를 포함할 수 있다.In one embodiment of the present invention, there is provided a dye-sensitized solar cell comprising: a step of subjecting a dye synthesized from a dye precursor to vacuum distillation, adding water and an organic solvent (1), and extracting only a layer of the organic solvent (1) And adding the organic solvent (2) to the extracted organic solvent (1) layer, followed by distillation under reduced pressure to remove the organic solvent (1).

다른 일 구현예는 염료 전구체로부터 합성된 염료를 결정화하여 여과하는 단계; 상기 여과된 염료에 물과 유기용매(1)를 가한 후 염료가 용해된 유기용매(1)층만 추출하는 단계; 및 상기 추출된 유기용매(1)층에 유기용매(2)를 가한 후 감압증류하여 유기용매(1)를 제거하는 단계;를 포함할 수 있다.Another embodiment comprises crystallizing and dyeing a dye synthesized from a dye precursor; Adding water and an organic solvent (1) to the filtered dye, and extracting only the organic solvent (1) layer in which the dye is dissolved; And adding the organic solvent (2) to the extracted organic solvent (1) layer, followed by distillation under reduced pressure to remove the organic solvent (1).

또 다른 일 구현예는 유기용매(1)가 끓는점이 120℃ 미만이며 물에 대한 용해도가 10% 이하인 용매이며, 상기 유기용매(2)는 끓는점이 120℃ 이상인 유기용매인 것일 수 있다.In another embodiment, the organic solvent (1) is a solvent having a boiling point of less than 120 ° C and a solubility in water of 10% or less, and the organic solvent (2) may be an organic solvent having a boiling point of 120 ° C or higher.

또 다른 일 구현예는 유기용매(1)가 디에틸에테르, 디클로로메탄, 클로로포름, 에틸아세테이트, 벤젠 및 톨루엔으로 이루어진 군으로부터 선택되는 1종 이상의 것이며, 상기 유기용매(2)는 프로필렌글리콜메틸에테르아세테이트, 프로필렌글리콜메틸에테르아세테이트, 프로필렌글리콜모노메틸에테르, 에톡시 3-에틸프로피오네이트, 시클로헥사논, 디아세톤알콜, 에틸락테이트, 디프로필렌글리콜모노메틸에테르, 디프로필렌글리콜모노메틸에테르아세테이트, 및 프로필렌글리콜 디아세테이트로 이루어진 군으로부터 선택되는 1종 이상인 것일 수 있다.In another embodiment, the organic solvent (1) is at least one selected from the group consisting of diethyl ether, dichloromethane, chloroform, ethyl acetate, benzene and toluene, and the organic solvent (2) is propylene glycol methyl ether acetate , Propylene glycol methyl ether acetate, propylene glycol monomethyl ether, ethoxy 3-ethyl propionate, cyclohexanone, diacetone alcohol, ethyl lactate, dipropylene glycol monomethyl ether, dipropylene glycol monomethyl ether acetate, and Propylene glycol diacetate, and propylene glycol diacetate.

또 다른 일 구현예는 염료 전구체가 하기 화학식 1로 표시되는 화합물인 것일 수 있다.In another embodiment, the dye precursor may be a compound represented by the following general formula (1).

[화학식 1][Chemical Formula 1]

Figure pat00001
Figure pat00001

상기 화학식 1에서, X는 할로겐 원소 또는 설포닐옥시기이다.In Formula 1, X is a halogen atom or a sulfonyloxy group.

또 다른 일 구현예는 염료가 하기 화학식 2로 표시되는 화합물인 것일 수 있다.In another embodiment, the dye may be a compound represented by the following formula (2).

[화학식 2](2)

Figure pat00002
Figure pat00002

상기 화학식 2에서, R1 내지 R4는 각각 독립적으로, 수소, 헤테로원자를 포함하거나 포함하지 않는 탄소수 1 내지 12의 지방족 탄화수소, 또는 치환되거나 비치환된 탄소수 6 내지 12의 방향족 탄화수소이며, R1과 R3 또는 R2와 R4는 서로 연결되어 고리를 이룰 수 있다.
In Formula 2, R 1 to R 4 each independently represent hydrogen, an aliphatic hydrocarbon having 1 to 12 carbon atoms, which may or may not contain a hetero atom, or a substituted or unsubstituted aromatic hydrocarbon having 6 to 12 carbon atoms, and R 1 And R 3 or R 2 and R 4 may be linked together to form a ring.

본 발명의 염료 마스터 배치 제조방법은 염료 합성 후 2단계의 분말상태의 정제염료 상태를 거치지 않고, 염료를 추출조작과 용매치환과정을 통하여 마스터 배치를 제조함으로써 제조시간을 줄이고 제조비용을 절감할 수 있는 장점이 있다.
The master batch preparation method of the present invention can reduce the manufacturing time and the manufacturing cost by preparing the master batch through the extraction operation of the dye and the solvent substitution process without going through the dye state of the powdery state after the dye synthesis There is an advantage.

도 1은 기존 염료 마스터 배치의 제조방법(비교예 1)과 본 발명의 염료 마스터 배치의 제조방법(실시예 2 및 3)의 공정 순서를 나타낸 것이다.FIG. 1 shows the process sequence of the conventional dye master batch manufacturing method (Comparative Example 1) and the dye master batch manufacturing method of the present invention (Examples 2 and 3).

이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.

마스터 배치(master batch)란 염료를 고농도로 농축하여 용해시켜 놓은 염료용액을 의미한다. 염료가 분말상태일 경우 다른 원료와의 혼합 시 사용하기가 어렵고 사용 중에 염료의 비산으로 인하여 주변 환경의 오염이 발생할 우려가 있으므로 염료 마스터 배치를 공정상에 사용하며, 이에 따라 염료 마스터 배치의 제조 공정을 단순화하는 것이 계속하여 요구되어 왔다.A master batch means a dye solution in which the dye is concentrated and dissolved at a high concentration. When the dye is in a powder state, it is difficult to use it in mixing with other raw materials, and since the scattering of the dye during use may cause contamination of the surrounding environment, the dye masterbatch is used in the process, Has continued to be demanded.

본 발명은 이러한 요구에 부응하여, 염료 마스터 배치를 제조하는 방법을 제공하며, 염료 합성 후 2단계의 분말상태의 정제염료 상태를 거치지 않고, 염료를 추출조작 용매치환과정을 통하여 염료 마스터 배치를 제조함으로써 제조시간을 줄이고 제조비용을 절감할 수 있다.
The present invention provides a method for producing a dye master batch in response to such a demand, and it is an object of the present invention to provide a dye master batch Thereby reducing manufacturing time and manufacturing cost.

구체적으로 본 발명은 염료 전구체로부터 합성된 염료에 물과 유기용매(1)를 가한 후 염료가 용해된 유기용매(1)층만 추출하는 단계; 및 상기 추출된 유기용매(1)층에 유기용매(2)를 가한 후 감압증류하여 유기용매(1)를 제거하는 단계;를 포함하며, 상기 유기용매(2)는 유기용매(1)보다 끓는점이 높은 것인, 염료 마스터 배치를 제조하는 방법을 제공한다. Specifically, the present invention relates to a method for producing a dye precursor comprising the steps of: adding water and an organic solvent (1) to a dye synthesized from a dye precursor, and then extracting only the organic solvent (1) And removing the organic solvent (1) by distillation under reduced pressure after adding the organic solvent (2) to the extracted organic solvent (1) layer, wherein the organic solvent (2) Is higher than that of the dye masterbatch.

상기 염료 전구체로부터 합성된 염료에 물과 유기용매(1)를 가하기 전에 감압증류과정을 더 포함할 수 있으며, 감압증류과정을 통해 합성 시의 잔존 반응물 및 용매를 제거할 수 있다.The dye precursor may further comprise a vacuum distillation process before the water and the organic solvent (1) are added to the dye. The residual reactants and the solvent may be removed through the vacuum distillation process.

또한, 상기 염료 전구체로부터 합성된 염료를 결정화하여 여과한 후, 결정화된 염료에 물과 유기용매(1)를 가하여 진행할 수도 있다.Further, the dye synthesized from the dye precursor may be crystallized and filtered, and then water and an organic solvent (1) may be added to the crystallized dye.

상기 염료 마스터 배치의 제조방법은 기존의 염료 합성 -> 염료결정화 -> 여과 -> 세정 -> 재용해 -> 결정화 -> 여과 -> 감압건조 -> 용제 투입과정에서의 결정화 회수를 줄이고 약 24시간 정도 소요되는 감압건조의 공정을 제외함으로써 제조시간과 제조비용을 절감할 수 있다.The method of preparing the dye master batch is to reduce the number of crystallization in the conventional dye synthesis-> dye crystallization-> filtration-> cleaning-> redissolution-> crystallization-> filtration-> vacuum drying-> It is possible to reduce manufacturing time and manufacturing cost.

상기 염료 전구체는 하기 화학식 1로 표시되는 화합물일 수 있으며, 염료는 하기 화학식 2로 표시되는 화합물일 수 있다.The dye precursor may be a compound represented by the following formula (1), and the dye may be a compound represented by the following formula (2).

[화학식 1][Chemical Formula 1]

Figure pat00003
Figure pat00003

상기 화학식 1에서, X는 할로겐 원소 또는 설포닐옥시기이다.In Formula 1, X is a halogen atom or a sulfonyloxy group.

[화학식 2](2)

Figure pat00004
Figure pat00004

상기 화학식 2에서, R1 내지 R4는 각각 독립적으로, 수소, 헤테로원자를 포함하거나 포함하지 않는 탄소수 1 내지 12의 지방족 탄화수소, 또는 치환되거나 비치환된 탄소수 6 내지 12의 방향족 탄화수소이며, R1과 R3 또는 R2와 R4는 서로 연결되어 고리를 이룰 수 있다. In Formula 2, R 1 to R 4 each independently represent hydrogen, an aliphatic hydrocarbon having 1 to 12 carbon atoms, which may or may not contain a hetero atom, or a substituted or unsubstituted aromatic hydrocarbon having 6 to 12 carbon atoms, and R 1 And R 3 or R 2 and R 4 may be linked together to form a ring.

상기 헤테로원자를 포함하는 탄소수 1 내지 12의 지방족 탄화수소는 헤테로원자인 질소, 인, 산소, 규소 또는 황 등을 포함하는 탄소수 1 내지 12의 지방족 탄화수소를 말한다. The aliphatic hydrocarbon having 1 to 12 carbon atoms including the hetero atom is an aliphatic hydrocarbon having 1 to 12 carbon atoms including a hetero atom such as nitrogen, phosphorus, oxygen, silicon, or sulfur.

헤테로원자를 포함하지 않는 탄소수 1 내지 12의 지방족 탄화수소는 알킬기, 시클로알킬기 등을 들 수 있으며, 알킬기로는 메틸기, 에틸기, 프로필기, 이소프로필기, 부틸기, 이소부틸기, 펜틸기, 헥실기, 헵틸기, 옥틸기, 1-메틸프로필기, 2-메틸프로필기, 1-메틸부틸기, 2-메틸부틸기, 2-에틸헥실기, 노닐기, 데카닐기, 1,1-디메틸프로필기, 1,2-디메틸프로필기, 2,2-디메틸프로필기 등을 들 수 있고, 시클로알킬기로는 시클로프로필기, 시클로부틸기, 시클로펜틸기, 시클로헥실기, 시클로헵틸기, 시클로옥틸기, 트리시클로데카닐기 등을 들 수 있다.Examples of the alkyl group include an alkyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group, a hexyl group Methylpropyl group, 1-methylbutyl group, 2-methylbutyl group, 2-ethylhexyl group, nonyl group, decanyl group, 1,1-dimethylpropyl group , A 1,2-dimethylpropyl group, and a 2,2-dimethylpropyl group. The cycloalkyl group includes a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, And a tricyclodecanyl group.

치환되거나 비치환된 탄소수 6 내지 12의 방향족 탄화수소는 벤젠, 톨루엔, 에틸벤젠, 크실렌(o-크실렌, m-크실렌, p-크실렌) 등을 들 수 있다.Examples of the substituted or unsubstituted aromatic hydrocarbon having 6 to 12 carbon atoms include benzene, toluene, ethylbenzene, xylene ( o -xylene, m -xylene, p -xylene) and the like.

예컨대, 상기 화학식 2는 화학식 2-1 또는 화학식 2-2로 표시되는 화합물일 수 있다.For example, Formula 2 may be a compound represented by Formula 2-1 or Formula 2-2.

[화학식 2-1][Formula 2-1]

Figure pat00005
Figure pat00005

[화학식 2-2][Formula 2-2]

Figure pat00006
Figure pat00006

상기 염료 전구체로부터 염료의 합성은 화학식 1로 표시되는 화합물에 1차 또는 2차 아민기를 포함하는 화합물로 치환 반응시킴으로써 이루어 질 수 있다. 상기 아민기를 포함하는 화합물은 상기 R1 및 R3로 이루어진 군으로부터 선택되는 1종 이상의 것, 또는 R2 및 R4로 이루어진 군으로 선택되는 1종 이상의 것을 포함하는 것일 수 있다. 아민기를 포함하는 화합물은 치환반응을 통해 화학식 1의 할로겐원자와 치환되어, 화학식 2의 구조를 갖게 된다.The synthesis of the dye from the dye precursor can be carried out by substituting the compound represented by the formula (1) with a compound containing a primary or secondary amine group. The amine compound containing a group R 1 is the And R < 3 >, or at least one selected from the group consisting of R < 2 > and R < 4 >. The compound containing an amine group is substituted with a halogen atom of the formula (1) through a substitution reaction to have a structure of the formula (2).

또한, 염료 전구체로부터 염료의 합성은 화학식 1로 표시되는 화합물에 1차 아민기를 포함하는 화합물로 치환 반응시켜 하기 화학식 3으로 표시되는 화합물로 합성한 후, 할로겐원소를 포함하는 화합물로 치환반응시켜 화학식 2로 표시되는 화합물을 합성할 수 있다.The dye may be synthesized from a dye precursor by a substitution reaction with a compound having a primary amine group and a compound represented by the following formula (1), followed by substitution reaction with a compound containing a halogen element, 2 can be synthesized.

[화학식 3](3)

Figure pat00007
Figure pat00007

상기 화학식 3에서, R5 및 R6는 각각 독립적으로, 헤테로원자를 포함하거나 포함하지 않는 탄소수 1 내지 12의 지방족 탄화수소, 또는 치환되거나 비치환된 탄소수 6 내지 12의 방향족 탄화수소이며, 구체적인 것은 앞서 설명한 바와 같다.In Formula 3, R 5 and R 6 are each independently an aliphatic hydrocarbon having 1 to 12 carbon atoms, which may or may not contain a heteroatom, or a substituted or unsubstituted aromatic hydrocarbon having 6 to 12 carbon atoms, Same as.

화학식 1로 표시되는 화합물에서 화학식 3으로 표시되는 화합물로의 합성에 사용되는 1차 아민기를 포함하는 화합물은 R5 또는 R6를 포함하며, 할로겐원소를 포함하는 화합물은 헤테로원자를 포함하거나 포함하지 않는 탄소수 1 내지 12의 지방족 탄화수소 또는 치환되거나 비치환된 탄소수 6 내지 12의 방향족 탄화수소를 포함할 수 있다.The compound containing a primary amine group used in the synthesis of the compound represented by the general formula (1) in the compound represented by the general formula (1) includes R 5 or R 6 , and the compound containing the halogen element contains or does not contain a hetero atom An aliphatic hydrocarbon having 1 to 12 carbon atoms or a substituted or unsubstituted aromatic hydrocarbon having 6 to 12 carbon atoms.

상기 치환반응 후의 반응물(합성된 염료)에 물과 유기용매(1)를 가하는데, 이때의 유기용매(1)는 끓는점이 120℃ 미만이며 물에 대한 용해도가 10% 이하인 용매일 수 있다. 구체적으로, 유기용매(1)는 디에틸에테르, 디클로로메탄, 클로로포름, 에틸아세테이트, 벤젠 및 톨루엔으로 이루어진 군으로부터 선택되는 1종 이상의 것일 수 있다.Water and an organic solvent (1) are added to the reaction product (synthesized dye) after the substitution reaction. The organic solvent (1) at this time may be a solvent having a boiling point of less than 120 ° C and a solubility in water of 10% or less. Specifically, the organic solvent (1) may be at least one selected from the group consisting of diethyl ether, dichloromethane, chloroform, ethyl acetate, benzene and toluene.

유기용매(1)를 가한 후, 찌꺼기가 있는 물층과 화학식 2로 표시되는 화합물이 용해된 유기용매(1)층을 분리하여 유기용매(1)층만 추출한 후, 마스터배치 용매로 사용되는 유기용매(2)를 가하는데, 이때의 유기용매(2)는 끓는 점이 120℃ 이상인 용매일 수 있다. 구체적으로, 유기용매(2)는 프로필렌글리콜메틸에테르아세테이트, 프로필렌글리콜메틸에테르아세테이트, 프로필렌글리콜모노메틸에테르,에톡시 3-에틸프로피오네이트, 시클로헥사논, 디아세톤알콜, 에틸락테이트, 디프로필렌글리콜모노메틸에테르, 디프로필렌글리콜모노메틸에테르아세테이트, 및 프로필렌글리콜 디아세테이트로 이루어진 군으로부터 선택되는 1종 이상의 것일 수 있다.After the organic solvent (1) is added, the organic solvent (1) layer in which the residue is dissolved and the organic solvent (1) layer in which the compound represented by the general formula (2) is dissolved is extracted and only the organic solvent (1) 2). The organic solvent (2) at this time may be a solvent having a boiling point of 120 ° C or higher. Specifically, the organic solvent (2) is at least one selected from the group consisting of propylene glycol methyl ether acetate, propylene glycol methyl ether acetate, propylene glycol monomethyl ether, ethoxy 3-ethyl propionate, cyclohexanone, diacetone alcohol, ethyl lactate, Glycol monomethyl ether, dipropylene glycol monomethyl ether acetate, and propylene glycol diacetate.

유기용매(2)를 가한 후, 유기용매(1)과 유기용매(2)와의 끓는점 차이를 통해 감압증류하여 유기용매(1)를 선택적으로 제거함으로써 염료 마스터 배치를 얻을 수 있다.After the organic solvent 2 is added, the organic solvent 1 is selectively removed by distillation under reduced pressure through the boiling point difference between the organic solvent 1 and the organic solvent 2 to obtain the dye master batch.

상기 염료 마스터 배치의 제조방법은 필요에 따라 부가적인 단계(공정)을 추가적으로 포함할 수 있다. 예컨대, 유기용매(1)층을 추출한 후 세정단계를 더 포함하거나 감압증류 후 정밀여과하는 단계를 더 포함할 수 있다.
The method of making the dye masterbatch may additionally include additional steps (processes) as needed. For example, it may further comprise a step of extracting the organic solvent (1) layer, followed by a step of washing, or a step of microfiltration after distillation under reduced pressure.

이하, 본 발명을 실시예 및 비교예를 이용하여 더욱 상세하게 설명한다. 그러나 하기 실시예 및 비교예는 본 발명을 예시하기 위한 것으로서, 본 발명은 하기 실시예 및 비교예에 의해 한정되지 않고 다양하게 수정 및 변경될 수 있다.
Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples. However, the following examples and comparative examples are provided for illustrating the present invention, and the present invention is not limited by the following examples and comparative examples, and can be variously modified and changed.

실시예Example 1 One

하기 화학식 1로 표시되는 화합물(40.5g, 0.1mol)을 NMP(N-메틸피롤리돈)(200g)에 녹이고, 디에틸아민(21.9g, 0.3mol)을 가한 뒤, 80℃에서 24시간 교반해 주어, 하기 화학식 2-1로 표시되는 화합물을 제조하고(하기 반응식 1 참조), 반응혼합물에 증류수(500g)와 디클로로메탄(200g)을 가하고, 분별깔대기를 이용하여, 화학식 2-1로 표시되는 화합물을 유기층으로 추출해내고, 얻어진 추출물에 증류수 500g을 재차 추가하여 동일하게 추출하여 유기용매층을 정재하였다.Diethylamine (21.9 g, 0.3 mol) was added to NMP (N-methylpyrrolidone) (200 g) and the mixture was stirred at 80 ° C for 24 hours Then, distilled water (500 g) and dichloromethane (200 g) were added to the reaction mixture, and a compound represented by the following formula (2-1) was prepared Was extracted into an organic layer, 500 g of distilled water was added again to the obtained extract, and the same extraction was carried out to prepare an organic solvent layer.

얻어진 유기용매층에 PGMEA(프로필렌글리콜메틸에테르아세테이트)(500g)을 가하고, 감압증류하여, 디클로로메탄을 선택적으로 제거하여, 화학식 2-1로 표시된 화합물이 약 10%녹아있는, PGMEA 용액을 얻었다.PGMEA (propyleneglycol methyl ether acetate) (500 g) was added to the obtained organic solvent layer and distilled under reduced pressure to selectively remove dichloromethane to obtain a PGMEA solution in which about 10% of the compound represented by the general formula (2-1) was dissolved.

[반응식 1][Reaction Scheme 1]

Figure pat00008

Figure pat00008

실시예Example 2 2

하기 화학식 3으로 표시되는 화합물(47.9g, 0.1mol)을 NMP(N-메틸피롤리돈)(200g)에 녹이고, 벤질클로라이드(38.0g, 0.3mol)을 가한 뒤, 80℃에서 48시간 교반해 주어, 하기 화학식 2-2로 표시되는 화합물을 제조하고, 반응혼합물에 증류수 (500g)을 가하여, 화학식 2-2로 표시되는 화합물의 미정제 상태의 침전을 얻었다. 얻어진 침전물은 거름종이가 설치된 필터를 이용하여 젖은 고체상태의 화학식 2로 표시되는 화합물을 얻었고 하였다(하기 반응식 2 참조). 젖은 고체상태의 침전물에 증류수 (500g)과 디클로로메탄(200g)을 가하고, 분별깔대기를 이용하여, 화학식 2-2로 표시되는 화합물을 유기층으로 추출해내고, 얻어진 추출물에 증류수 500g을 재차 추가하여 동일하게 추출하여 유기용매층을 정재하였다.Benzyl chloride (38.0 g, 0.3 mol) was added to the solution, and the mixture was stirred at 80 ° C for 48 hours. Subjectively, a compound represented by the following formula (2-2) was prepared, and distilled water (500 g) was added to the reaction mixture to obtain a precipitate in a crude state of the compound represented by the formula (2-2). The resulting precipitate was obtained by using a filter equipped with a filter paper to obtain a compound represented by Chemical Formula 2 in a wet solid state (see the following Reaction Scheme 2). Distilled water (500 g) and dichloromethane (200 g) were added to the precipitate in a wet solid state, and the compound represented by the formula (2-2) was extracted into an organic layer using a separating funnel. 500 g of distilled water was added again to the obtained extract, And the organic solvent layer was recovered.

얻어진 유기용매층에 PGMEA(프로필렌글리콜메틸에테르아세테이트)(500g)을 가하고, 감압증류하여, 디클로로메탄을 선택적으로 제거하여, 화학식 2-2로 표시되는 화합물이 약 10%녹아있는, PGMEA 용액을 얻었다.
PGMEA (propyleneglycol methyl ether acetate) (500 g) was added to the obtained organic solvent layer and distilled under reduced pressure to selectively remove dichloromethane to obtain a PGMEA solution in which about 10% of the compound represented by the general formula (2-2) was dissolved .

실시예Example 3 3

하기 화학식 3으로 표시되는 화합물(47.9g, 0.1mol)을 NMP(N-메틸피롤리돈)(200g)에 녹이고, 벤질아민(38.1g, 0.3mol)을 가한 뒤, 80℃에서 48시간 교반해 주어, 하기 화학식 2-2로 표시되는 화합물을 제조하고(하기 반응식 2 참조), 반응 혼합물을 감압증류하여 잔존 반응물 및 용매를 제거하고, 반응혼합물에 증류수 (500g)과 디클로로메탄(200g)을 가하고, 분별깔대기를 이용하여, 화학식 2-2로 표시되는 화합물을 유기층으로 추출해내고, 얻어진 추출물에 증류수 500g을 재차 추가하여 동일하게 추출하여 유기용매층을 정재하였다.Benzylamine (38.1 g, 0.3 mol) was added to NMP (N-methylpyrrolidone) (200 g), and the mixture was stirred at 80 ° C for 48 hours The reaction mixture was distilled under reduced pressure to remove the residual reactants and the solvent. Distilled water (500 g) and dichloromethane (200 g) were added to the reaction mixture, The compound represented by the formula (2-2) was extracted into an organic layer using a separating funnel, and 500 g of distilled water was added again to the obtained extract to extract the organic solvent layer.

얻어진 유기용매층에 PGMEA(프로필렌글리콜메틸에테르아세테이트)(500g)을 가하고, 감압증류하여, 디클로로메탄을 선택적으로 제거하여, 화학식 2-2로 표시되는 화합물이 약 10%녹아있는, PGMEA 용액을 얻었다.PGMEA (propyleneglycol methyl ether acetate) (500 g) was added to the obtained organic solvent layer and distilled under reduced pressure to selectively remove dichloromethane to obtain a PGMEA solution in which about 10% of the compound represented by the general formula (2-2) was dissolved .

[반응식 2][Reaction Scheme 2]

Figure pat00009

Figure pat00009

비교예Comparative Example 1 One

상기 반응식 1과 같이 합성함에 있어서, 화학식 1로 표시되는 화합물(40.5g, 0.1mol)을 NMP(N-메틸피롤리돈)(200g)에 녹이고, 디에틸아민(21.9g, 0.3mol)을 가한 뒤, 80℃에서 24시간 교반해 주어, 화학식 2로 표시되는 화합물을 제조하고, 반응혼합물에 증류수 (500g)을 가하여, 화학식 2로 표시되는 화합물의 침전을 얻었다. 얻어진 침전물은 거름종이가 설치된 필터를 이용하여 젖은 고체상태의 화학식 2로 표시되는 화합물을 얻었고, 공침되어 있는 불순물을 제거 하기 위해서 증류수 (500g)을 추가적으로 필터를 통하여 흘려주어 세정해 주었다. 세정 후 여전히 존재하는 불순물을 제거하기 위해서, 얻어진 젖어있는 고체 생성물을 메탄올(200g)에 녹이고, 증류수(500g)을 추가하여, 또 다시, 화학식 2로 표시되는 화합물의 침전물을 얻었고, 얻어진 침전물은 필터를 통하여, 젖은 상태의 고체 생성물을 얻었고, 잔존 용매를 제거하기 위해서, 100℃ 오븐에서 24시간 건조하여, 분말상태의 화학식 2로 표시되는 화합물을 얻었고, 얻어진 분말 47g을 PGMEA (450g)에 녹여서, 화학식 2로 표시되는 화합물이 약 10%녹아있는, PGMEA 용액을 얻었다.(40.5 g, 0.1 mol) was dissolved in NMP (N-methylpyrrolidone) (200 g), and diethylamine (21.9 g, 0.3 mol) was added thereto Thereafter, the mixture was stirred at 80 DEG C for 24 hours to prepare a compound represented by the formula (2), and distilled water (500 g) was added to the reaction mixture to obtain a precipitate of the compound represented by the formula (2). The obtained precipitate was filtered using a filter equipped with filter paper to obtain a compound represented by Chemical Formula 2 in the form of a wet solid, and 500 g of distilled water (500 g) was further flowed through the filter in order to remove coprecipitated impurities. The wet solid product thus obtained was dissolved in methanol (200 g) and distilled water (500 g) was added to obtain a precipitate of the compound represented by the general formula (2). The resulting precipitate was filtered through a filter To obtain a wet solid product and dried in an oven at 100 DEG C for 24 hours to obtain a compound represented by the formula (2) in a powder state, and 47 g of the obtained powder was dissolved in 450 g of PGMEA, To obtain a PGMEA solution in which about 10% of the compound represented by the general formula (2) was dissolved.

그 결과, 비교예 대비 상기 실시예는 염료를 재결정화하는 단계를 포함하지 않아 제조시간이 마스터 배치 제조시간이 단축됨을 확인하였다.As a result, it was confirmed that the above example of the comparative example does not include the step of recrystallizing the dye, so that the production time shortens the master batch production time.

Claims (7)

염료 전구체로부터 합성된 염료에 물과 유기용매(1)를 가한 후 염료가 용해된 유기용매(1)층만 추출하는 단계; 및
상기 추출된 유기용매(1)층에 유기용매(2)를 가한 후 감압증류하여 유기용매(1)를 제거하는 단계;를 포함하며,
상기 유기용매(2)는 유기용매(1)보다 끓는점이 높은 것인, 염료 마스터 배치를 제조하는 방법.Adding water and an organic solvent (1) to a dye synthesized from a dye precursor, and extracting only the organic solvent (1) layer in which the dye is dissolved; And
Adding an organic solvent (2) to the extracted organic solvent (1) layer, and distilling the organic solvent (1) under reduced pressure to remove the organic solvent (1)
Wherein the organic solvent (2) has a higher boiling point than the organic solvent (1). 청구항 1에 있어서, 염료 전구체로부터 합성된 염료를 감압증류하고 물과 유기용매(1)를 가한 후 염료가 용해된 유기용매(1)층만 추출하는 단계; 및
상기 추출된 유기용매(1)층에 유기용매(2)를 가한 후 감압증류하여 유기용매(1)를 제거하는 단계;를 포함하는, 염료 마스터 배치를 제조하는 방법.[2] The method according to claim 1, further comprising the steps of: distilling the dye synthesized from the dye precursor under reduced pressure, adding water and an organic solvent (1), and extracting only the organic solvent (1) And
Adding an organic solvent (2) to the extracted organic solvent (1) layer, and distilling the organic solvent (1) under reduced pressure to remove the organic solvent (1). 청구항 1에 있어서, 염료 전구체로부터 합성된 염료를 결정화하여 여과하는 단계;
상기 여과된 염료에 물과 유기용매(1)를 가한 후 염료가 용해된 유기용매(1)층만 추출하는 단계; 및
상기 추출된 유기용매(1)층에 유기용매(2)를 가한 후 감압증류하여 유기용매(1)를 제거하는 단계;를 포함하는, 염료 마스터 배치를 제조하는 방법.The method of claim 1, further comprising crystallizing and dyeing the dye synthesized from the dye precursor;
Adding water and an organic solvent (1) to the filtered dye, and extracting only the organic solvent (1) layer in which the dye is dissolved; And
Adding an organic solvent (2) to the extracted organic solvent (1) layer and then distilling off the organic solvent (1) under reduced pressure to remove the organic solvent (1). 청구항 1에 있어서, 상기 유기용매(1)는 끓는점이 120℃ 미만이며 물에 대한 용해도가 10% 이하인 용매이며, 상기 유기용매(2)는 끓는 점이 120℃ 이상인 유기용매인 것인, 염료 마스터 배치를 제조하는 방법.The method of claim 1, wherein the organic solvent (1) is a solvent having a boiling point of less than 120 ° C and a solubility in water of 10% or less, and the organic solvent (2) is an organic solvent having a boiling point of 120 ° C or higher. ≪ / RTI > 청구항 1에 있어서, 상기 유기용매(1)는 디에틸에테르, 디클로로메탄, 클로로포름, 에틸아세테이트, 벤젠 및 톨루엔으로 이루어진 군으로부터 선택되는 1종 이상의 것이며,
상기 유기용매(2)는 프로필렌글리콜메틸에테르아세테이트, 프로필렌글리콜메틸에테르아세테이트, 프로필렌글리콜모노메틸에테르, 에톡시 3-에틸프로피오네이트, 시클로헥사논, 디아세톤알콜, 에틸락테이트, 디프로필렌글리콜모노메틸에테르, 디프로필렌글리콜모노메틸에테르아세테이트, 및 프로필렌글리콜 디아세테이트로 이루어진 군으로부터 선택되는 1종 이상의 것인, 염료 마스터 배치를 제조하는 방법.The method of claim 1, wherein the organic solvent (1) is at least one selected from the group consisting of diethyl ether, dichloromethane, chloroform, ethyl acetate, benzene, and toluene,
The organic solvent (2) is at least one selected from the group consisting of propylene glycol methyl ether acetate, propylene glycol methyl ether acetate, propylene glycol monomethyl ether, ethoxy 3-ethyl propionate, cyclohexanone, diacetone alcohol, ethyl lactate, dipropylene glycol mono Methyl ether, dipropylene glycol monomethyl ether acetate, and propylene glycol diacetate. ≪ RTI ID = 0.0 > 11. < / RTI > 청구항 1에 있어서, 상기 염료 전구체는 하기 화학식 1로 표시되는 화합물인, 염료 마스터 배치를 제조하는 방법.
[화학식 1]
Figure pat00010

상기 화학식 1에서, X는 할로겐 원소 또는 설포닐옥시기이다.The method of claim 1, wherein the dye precursor is a compound represented by the following formula (1).
[Chemical Formula 1]
Figure pat00010

In Formula 1, X is a halogen atom or a sulfonyloxy group. 청구항 1에 있어서, 상기 염료는 하기 화학식 2로 표시되는 화합물인, 염료 마스터 배치를 제조하는 방법.
[화학식 2]
Figure pat00011

상기 화학식 2에서, R1 내지 R4는 각각 독립적으로, 수소, 헤테로원자를 포함하거나 포함하지 않는 탄소수 1 내지 12의 지방족 탄화수소, 또는 치환되거나 비치환된 탄소수 6 내지 12의 방향족 탄화수소이며,
R1과 R3 또는 R2와 R4는 서로 연결되어 고리를 이룰 수 있다.The method according to claim 1, wherein the dye is a compound represented by the following formula (2).
(2)
Figure pat00011

In Formula 2, R 1 to R 4 each independently represent hydrogen, an aliphatic hydrocarbon having 1 to 12 carbon atoms, which may or may not contain a hetero atom, or a substituted or unsubstituted aromatic hydrocarbon having 6 to 12 carbon atoms,
R 1 and R 3 or R 2 and R 4 may be linked together to form a ring.
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