[go: up one dir, main page]

CN111527075B - Xanthene-based compound and photosensitive resin composition containing the same, photosensitive material, color filter, and display device - Google Patents

Xanthene-based compound and photosensitive resin composition containing the same, photosensitive material, color filter, and display device Download PDF

Info

Publication number
CN111527075B
CN111527075B CN201880084202.5A CN201880084202A CN111527075B CN 111527075 B CN111527075 B CN 111527075B CN 201880084202 A CN201880084202 A CN 201880084202A CN 111527075 B CN111527075 B CN 111527075B
Authority
CN
China
Prior art keywords
group
chemical formula
carbon atoms
substituted
same
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.)
Active
Application number
CN201880084202.5A
Other languages
Chinese (zh)
Other versions
CN111527075A (en
Inventor
朴锺镐
崔相雅
李多美
郑智惠
梁承秦
李永熙
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LG Chem Ltd
Original Assignee
LG Chem Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority claimed from PCT/KR2018/013706 external-priority patent/WO2019194384A1/en
Publication of CN111527075A publication Critical patent/CN111527075A/en
Application granted granted Critical
Publication of CN111527075B publication Critical patent/CN111527075B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic 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
    • C07D311/78Ring systems having three or more relevant rings
    • C07D311/80Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82Xanthenes
    • C07D311/90Xanthenes with hydrocarbon radicals, substituted by amino radicals, directly attached in position 9
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00Optical elements other than lenses
    • G02B5/20Filters
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007Filters, e.g. additive colour filters; Components for display devices
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/09Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Architecture (AREA)
  • Structural Engineering (AREA)
  • Materials For Photolithography (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Optical Filters (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present specification provides a compound represented by chemical formula 1, and a photosensitive resin composition, a photosensitive material, a color filter, and a display device including the same.

Description

呫吨系化合物及包含其的感光性树脂组合物、感光材料、滤色 器、以及显示装置Xanthene compound and photosensitive resin composition, photosensitive material, color filter, and display device containing the same

技术领域Technical Field

本申请主张于2018年04月05日向韩国专利局提交的韩国专利申请第10-2018-0039901号的优先权,其全部内容包含在本说明书中。This application claims the priority of Korean Patent Application No. 10-2018-0039901 filed in the Korean Intellectual Property Office on April 5, 2018, the entire contents of which are incorporated herein by reference.

本申请主张于2018年11月06日向韩国专利局提交的韩国专利申请第10-2018-0135250号的优先权,其全部内容包含在本说明书中。This application claims the priority of Korean Patent Application No. 10-2018-0135250 filed in the Korean Intellectual Property Office on November 6, 2018, the entire contents of which are incorporated herein by reference.

本说明书涉及呫吨系化合物及包含其的感光性树脂组合物。此外,本说明书涉及利用上述感光性树脂组合物制造的感光材料、滤色器、以及包含其的显示装置。The present invention relates to a xanthene compound and a photosensitive resin composition containing the same. In addition, the present invention relates to a photosensitive material and a color filter produced using the photosensitive resin composition, and a display device containing the same.

背景技术Background Art

近年来,滤色器要求以高亮度、高对比度为特征的性能。此外,显示装置开发的主要目的之一是通过提高颜色纯度而实现显示元件性能的差别化及提高制造工序的生产率。In recent years, color filters are required to have high brightness and high contrast. In addition, one of the main goals of display device development is to achieve differentiation of display element performance and improve the productivity of the manufacturing process by improving color purity.

由于以往作为滤色器的色料而使用的颜料类型以粒子分散状态存在于彩色光致抗蚀剂中,因此在通过调节颜料粒子大小和分布来调节亮度和对比度方面存在困难。在颜料粒子的情况下,在滤色器内凝聚而溶解和分散性降低,并且由于凝聚(aggregation)的大粒子而发生光的多重散射(multiple scattering)。这种偏振的光的散射被视为是降低对比度的主要原因。虽然人们持续努力通过颜料的超微粒化和分散稳定化而提高亮度和对比度,但在用于实现高颜色纯度显示装置用色坐标的色料选定中自由度受限。此外,利用已经开发的色料尤其是颜料的颜料分散法在提高利用其的滤色器的颜色纯度、亮度和对比度方面达到了极限。Since the pigment type used as the colorant of the color filter in the past exists in the color photoresist in a particle dispersion state, there are difficulties in adjusting the brightness and contrast by adjusting the pigment particle size and distribution. In the case of pigment particles, the dissolution and dispersibility are reduced by condensation in the color filter, and multiple scattering of light occurs due to the large particles of condensation (aggregation). The scattering of this polarized light is considered to be the main reason for reducing the contrast. Although people continue to make efforts to improve brightness and contrast by ultra-micronization and dispersion stabilization of pigment, the freedom is limited in the colorant selection for realizing the color coordinates of high color purity display devices. In addition, the pigment dispersion method using the colorant, especially the pigment, which has been developed, has reached the limit in improving the color purity, brightness and contrast of the color filter using it.

由此,要求开发能够通过提高颜色纯度而提高色彩再现、亮度和对比度的新型色料。Therefore, there is a demand for the development of new colorants that can improve color reproduction, brightness, and contrast by improving color purity.

发明内容Summary of the invention

技术课题Technical issues

本发明人旨在提供新型结构的呫吨系化合物、包含其的感光性树脂组合物、利用其制造的感光材料、滤色器、以及包含其的显示装置。The present inventors aim to provide a xanthene compound having a novel structure, a photosensitive resin composition containing the same, a photosensitive material and a color filter produced using the same, and a display device containing the same.

课题的解决方法Solution to the problem

本说明书的一实施方式提供由下述化学式1表示的化合物。One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[化学式1][Chemical formula 1]

在上述化学式1中,In the above chemical formula 1,

L1和L2彼此相同或不同,各自独立地为取代或未取代的亚烷基,L1 and L2 are the same or different from each other and are each independently a substituted or unsubstituted alkylene group,

R1和R2彼此相同或不同,各自独立地为含有氮原子的二酐基团,R1 and R2 are the same or different from each other and are each independently a dianhydride group containing a nitrogen atom,

R3和R4彼此相同或不同,各自独立地为取代或未取代的烷基、或者取代或未取代的芳基,R3 and R4 are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,

R5至R12彼此相同或不同,各自独立地选自氢、氘、卤素基团、-OH、-SO3H、-SO3M、-SO2NM1M2、-SO2NHY、-COOH、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的烯基、取代或未取代的环烯基、取代或未取代的芳基、以及取代或未取代的杂芳基,R5 to R12 are the same as or different from each other, and are each independently selected from hydrogen, deuterium, a halogen group, -OH, -SO 3 H, -SO 3 M, -SO 2 NM1M2, -SO 2 NHY, -COOH, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group,

R13至R17彼此相同或不同,各自独立地为氢、氘、卤素基团、-OH、-SO3 -、-SO3H、-SO3M、-SO2NM1M2、-SO2NHY、-COOH、阴离子性基团、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的芳基、或者取代或未取代的杂芳基,R13 to R17 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, -OH, -SO 3 - , -SO 3 H, -SO 3 M, -SO 2 NM1M2, -SO 2 NHY, -COOH, an anionic group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

上述M选自Na+、K+、Rb+、Cs+、Fr+、以及包含铵结构的部分,The above-mentioned M is selected from Na + , K + , Rb + , Cs + , Fr + , and a part containing an ammonium structure,

上述M1、M2和Y彼此相同或不同,各自独立地选自取代或未取代的烷基、取代或未取代的芳基、以及取代或未取代的杂芳基,上述R13至R17中的至少一个为阴离子性基团,The above-mentioned M1, M2 and Y are the same as or different from each other, and are independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl. At least one of the above-mentioned R13 to R17 is an anionic group.

X为阴离子性基团,X is an anionic group,

a为0或1,a is 0 or 1,

r5和r6为0至4的整数,r5为2以上时,R5彼此相同或不同,r6为2以上时,R6彼此相同或不同。r5 and r6 are integers of 0 to 4. When r5 is 2 or more, R5s are the same or different from each other. When r6 is 2 or more, R6s are the same or different from each other.

本说明书的一实施方式提供包含由上述化学式1表示的化合物、粘合剂树脂、多官能性单体、光聚合引发剂、以及溶剂的感光性树脂组合物。One embodiment of the present specification provides a photosensitive resin composition including the compound represented by the above Chemical Formula 1, a binder resin, a multifunctional monomer, a photopolymerization initiator, and a solvent.

本说明书的一实施方式提供利用上述感光性树脂组合物制造的感光材料。One embodiment of the present specification provides a photosensitive material produced using the photosensitive resin composition.

本说明书的一实施方式提供包含上述感光材料的滤色器。One embodiment of the present specification provides a color filter including the above-mentioned photosensitive material.

本说明书的一实施方式提供包含上述滤色器的显示装置。One embodiment of the present specification provides a display device including the above-mentioned color filter.

发明效果Effects of the Invention

根据本说明书的一实施方式的化合物可以在感光性树脂组合物中作为色料使用,通过具有对有机溶剂的溶解度,从而可以减少分散工序,与以往的应用颜料时需要经过分散工序的情况不同,可以用经济的方法使用化合物作为色料。此外,通过减少荧光强度,从而能够在不添加追加的颜料的情况下提高对比度。The compound according to one embodiment of the present specification can be used as a colorant in a photosensitive resin composition, and by having solubility in an organic solvent, the dispersion process can be reduced, and unlike the case where a dispersion process is required when applying a pigment in the past, the compound can be used as a colorant in an economical manner. In addition, by reducing the fluorescence intensity, the contrast can be improved without adding an additional pigment.

另外,根据本说明书的一实施方式的呫吨系化合物作为色料使用,从而可以提高色彩再现、亮度和对比度。In addition, the xanthene-based compound according to one embodiment of the present specification is used as a colorant to improve color reproduction, brightness, and contrast.

附图说明BRIEF DESCRIPTION OF THE DRAWINGS

图1是表示利用根据本说明书的部分实施例和比较例的化合物制造的基板的被检测的荧光强度的图。FIG. 1 is a graph showing the detected fluorescence intensity of a substrate manufactured using compounds according to some examples and comparative examples of the present specification.

图2表示根据本说明书的一实施方式的化合物的视觉 FIG. 2 shows the visual properties of a compound according to one embodiment of the present specification.

图3表示利用根据本说明书的部分实施例和比较例的化合物制造的基板的透射率。FIG. 3 shows the transmittance of substrates manufactured using compounds according to some examples and comparative examples of the present specification.

具体实施方式DETAILED DESCRIPTION

下面,对本说明书更详细地进行说明。Next, this specification is described in more detail.

本说明书中,当指出某一构件位于另一个构件“上”时,其不仅包含某一构件与另一构件接触的情况,还包括两构件之间存在其它构件的情况。In this specification, when it is stated that a certain component is located “on” another component, it not only includes a case where the certain component is in contact with the other component, but also includes a case where other components are present between the two components.

本说明书中,当指出某一部分“包含”某一构成要素时,只要没有特别相反的记载,则意味着可以进一步包含其它构成要素,而不是将其它构成要素排除。In the present specification, when it is stated that a certain part “includes” a certain constituent element, unless there is a particular description to the contrary, it means that other constituent elements may be further included, rather than excluding other constituent elements.

根据本说明书的一实施方式,提供由上述化学式1表示的化合物。According to one embodiment of the present specification, a compound represented by the above Chemical Formula 1 is provided.

本发明通过包含由上述化学式1表示的化合物,从而在有机溶剂中具有优异的溶解度。具体而言,上述化学式1通过在呫吨(Xanthene)结构的氮上取代的芳基被含有硫(S)的取代基取代,并包含如含有氮原子的二酐基团等体积的大的取代基,从而可以增加在有机溶剂中的溶解度。The present invention has excellent solubility in organic solvents by including a compound represented by the above chemical formula 1. Specifically, the above chemical formula 1 can increase the solubility in organic solvents by replacing the aryl group substituted on the nitrogen of the xanthene structure with a substituent containing sulfur (S) and including a bulky substituent such as a dianhydride group containing a nitrogen atom.

另外,上述化学式1在呫吨结构的氮上取代的芳基被含有硫(S)的取代基取代的情况下,与被不含有硫(S)的取代基取代的情况相比,荧光强度减少,在不添加追加的颜料的情况下,也可以得到优异的对比度。In addition, when the aromatic group substituted on the nitrogen of the xanthene structure in the above Chemical Formula 1 is substituted with a substituent containing sulfur (S), the fluorescence intensity is reduced compared to the case where it is substituted with a substituent not containing sulfur (S), and excellent contrast can be obtained without adding an additional pigment.

由此带来溶解度增加,因而可以防止色料间的凝聚,减少色料分散所需的材料的量,从而可以提高经济性。This leads to an increase in solubility, thereby preventing aggregation of pigments and reducing the amount of material required for pigment dispersion, thereby improving economic efficiency.

另外,能够提高对比度(CR,Contrast Ratio),并且可以具有优异的耐热性。为了减少分子的发光(荧光或磷光),有减少分子内的平面性或导入吸收光的分子的方法。在导入吸收光的分子时,由于将需要的进行发光的分子的光以及外部的光全部进行吸收,因此难以选择性地只吸收发光波长的光。因此,为了减少分子内的平面性而导入空间阻位大的取代基(bulky group)。In addition, the contrast ratio (CR) can be improved, and excellent heat resistance can be achieved. In order to reduce the luminescence (fluorescence or phosphorescence) of the molecule, there are methods of reducing the planarity within the molecule or introducing molecules that absorb light. When introducing molecules that absorb light, it is difficult to selectively absorb only the light of the luminescent wavelength because all the light of the molecules that need to emit light and the external light are absorbed. Therefore, in order to reduce the planarity within the molecule, a bulky group with large steric hindrance is introduced.

在基态(ground state)吸收光而成为激发态(excited state)的分子通过振动模式(vibration mode)或旋转模式(rotation mode)移动能量时,可以发生非辐射衰减(non-radiative decay)。即,可以减少发光。When a molecule in an excited state absorbs light in its ground state and transfers energy through a vibration mode or a rotation mode, non-radiative decay can occur, that is, light emission can be reduced.

平面性越大,非辐射衰减越困难,从而增加发光的强度,导入大取代基而越减小平面面积,通过非辐射衰减,越可以减少发光的强度。为了非辐射衰减,可以导入长度长的烷基(alkyl group)、支链型烷基(branch ed alkyl group)、烷氧基(alkoxy group)、胺基(amine group)。但是烷基(alkyl)的情况下,具有耐热性不足的缺点。The greater the planarity, the more difficult the non-radiative attenuation is, thereby increasing the intensity of the luminescence. By introducing a large substituent and reducing the planar area, the intensity of the luminescence can be reduced by non-radiative attenuation. For non-radiative attenuation, long alkyl groups, branched alkyl groups, alkoxy groups, and amine groups can be introduced. However, in the case of alkyl groups, there is a disadvantage of insufficient heat resistance.

而且,在烷氧基(alkoxy)和胺基(amine group)的情况下,作为供电子基团(electron donating group)而发挥作用,从而可以改变吸收光的分子的吸收波长。Furthermore, in the case of an alkoxy group and an amine group, they function as electron donating groups, thereby being able to change the absorption wavelength of the molecule that absorbs light.

与此相比,在导入含有硫(S)的分子时,在吸收光的分子中,供电子基团(electrondonating group)的作用等减少,可以维持耐热性。In contrast, when molecules containing sulfur (S) are introduced, the effect of electron donating groups in the molecules that absorb light is reduced, and heat resistance can be maintained.

在导入与碳、氮、氧相比原子尺寸大的硫原子(sulfur atom)时,被激发的分子的能量向具有各种能级的硫原子(sulfur atom)移动,在硫原子的各种能级之间移动,即根据振动模式(vibration mode)、旋转模式(rotation mode)移动,同时可以发生非辐射衰减(non-radiative decay)。由于这样的特性,在导入硫原子(sulfur atom)时,可以减少分子内的发光的强度。When sulfur atoms, which are larger in size than carbon, nitrogen, and oxygen, are introduced, the energy of the excited molecules moves to sulfur atoms having various energy levels, and moves between the various energy levels of sulfur atoms, that is, according to vibration modes and rotation modes, and non-radiative decay can occur at the same time. Due to such characteristics, when sulfur atoms are introduced, the intensity of luminescence in the molecule can be reduced.

将具有发光的分子应用于液晶显示器(LCD)时,引起对比度(CR,Contrast Ratio)的减少而可能成为品质降低的问题。因此,采取了各种方法试图减少发光。When molecules that emit light are used in liquid crystal displays (LCDs), the contrast ratio (CR) decreases, which may cause quality degradation. Therefore, various methods have been adopted to try to reduce the light emission.

现在为了抑制对比度(CR,Contrast Ratio)减少而投入吸收发光的分子。但是发生颜色纯度降低和色料使用量增加。Currently, molecules that absorb light are added to suppress the decrease in contrast ratio (CR), but this results in a decrease in color purity and an increase in the amount of colorant used.

由上述化学式1表示的化合物的取代基的示例在下文中进行说明,但并不限定于此。Examples of substituents of the compound represented by the above Chemical Formula 1 are described below, but are not limited thereto.

本说明书中,是指与其它取代基或结合部结合的部位。In this manual, It refers to the site that bonds to other substituents or bonding parts.

在本说明书中“取代或未取代的”这一用语的意思是被选自氘;卤素基团;腈基;硝基;-OH;羰基;酯基;-COOH;酰亚胺基;酰胺基;阴离子性基团;烷氧基;烷基;环烷基;烯基;环烯基;芳烷基;膦基;磺酸酯/盐基;胺基;芳基;杂芳基;甲硅烷基;硼基;丙烯酰基;丙烯酸酯基;醚基;含有N、O、S或P原子中的1个以上的杂环基和阴离子性基团中的1个以上的取代基取代或不具有任何取代基。The term "substituted or unsubstituted" in this specification means that the group is substituted with or has no substituent selected from deuterium; a halogen group; a nitrile group; a nitro group; a -OH group; a carbonyl group; an ester group; a -COOH group; an imide group; an amide group; an anionic group; an alkoxy group; an alkyl group; a cycloalkyl group; an alkenyl group; a cycloalkenyl group; an aralkyl group; a phosphino group; a sulfonate group; an amine group; an aryl group; a heteroaryl group; a silyl group; a boryl group; an acryloyl group; an acrylate group; an ether group; a heterocyclic group containing one or more N, O, S or P atoms and one or more substituents selected from anionic groups.

本说明书中,“相邻的”基团可以表示在与该取代基取代的原子直接连接的原子上取代的取代基、与该取代基在立体结构上最接近的取代基、或者在该取代基取代的原子上取代的其它取代基。例如,在苯环中以邻(ortho)位被取代的2个取代基以及在脂肪族环中在同一碳上取代的2个取代基可以解释为彼此“相邻的”基团。In this specification, "adjacent" groups may refer to substituents substituted on atoms directly connected to the atom substituted by the substituent, substituents closest to the substituent in stereostructure, or other substituents substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as "adjacent" groups to each other.

本说明书中,相邻的基团可以结合而形成“环”中的上述环是指芳香族或脂肪族环。具体而言,上述环可以为芳香族环,可以为芳基或杂芳基。上述芳基和杂芳基可以适用后述的说明。In this specification, the adjacent groups may be combined to form a "ring" and the above-mentioned ring refers to an aromatic or aliphatic ring. Specifically, the above-mentioned ring may be an aromatic ring, an aryl group or a heteroaryl group. The above-mentioned aryl group and heteroaryl group may be applied to the following description.

本说明书中,作为卤素基团的例子,有氟、氯、溴或碘。In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

本说明书中,上述羰基可以由–COR表示,上述R可以为氢、氘、取代或未取代的烷基、取代或未取代的环烷基、或者取代或未取代的芳基。上述羰基的碳原子数没有特别限定,但优选碳原子数为1至30。具体而言,可以为如下结构的化合物,但并不限定于此。In the present specification, the carbonyl group may be represented by -COR, and the R may be hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group. The number of carbon atoms in the carbonyl group is not particularly limited, but preferably the number of carbon atoms is 1 to 30. Specifically, the compound may be of the following structure, but is not limited thereto.

本说明书中,上述酯基可以由-COOR表示,上述R可以为氢、氘、取代或未取代的烷基、取代或未取代的环烷基、或者取代或未取代的芳基。上述酯基中,酯基的氧可以被碳原子数1至25的直链、支链或环状烷基、或者碳原子数6至30的芳基取代。具体而言,可以为下述结构式的化合物,但并不限定于此。In this specification, the ester group can be represented by -COOR, and the R can be hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl. In the ester group, the oxygen of the ester group can be substituted by a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, it can be a compound of the following structural formula, but is not limited thereto.

本说明书中,酰亚胺基的碳原子数没有特别限定,但优选碳原子数为1至30。具体而言,可以为如下结构的化合物,但并不限定于此。In the present specification, the number of carbon atoms in the imide group is not particularly limited, but preferably the number of carbon atoms is 1 to 30. Specifically, the compound may have the following structure, but is not limited thereto.

本说明书中,酰胺基中,酰胺基的氮可以被氢、碳原子数1至30的直链、支链或环状烷基、或碳原子数6至30的芳基取代。具体而言,可以为下述结构式的化合物,但并不限定于此。In the present specification, in the amide group, the nitrogen of the amide group may be substituted by hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, the compound may be of the following structural formula, but is not limited thereto.

本说明书中,膦基是指烷基膦基或芳基膦基,上述烷基膦基是指被烷基取代的膦基。上述烷基膦基的碳原子数没有特别限定,但优选1至20。作为上述烷基膦基的例子,有二甲基膦基、二乙基膦基、二正丙基膦基、二异丙基膦基、二正丁基膦基、二仲丁基膦基、二叔丁基膦基、二异丁基膦基、叔丁基异丙基膦基、二正己基膦基、二正辛基膦基、二正甲基膦基等,但并不限定于此。上述芳基膦基是指被芳基取代的膦基。上述芳基膦基的碳原子数没有特别限定,但优选6至30。作为上述芳基膦基的例子,有二苯基膦基、二苄基膦基、甲基苯基膦基、苄基己基膦基、双三甲基甲硅烷基膦基等,但并不限定于此。In this specification, the phosphino group refers to an alkyl phosphino group or an aryl phosphino group, and the alkyl phosphino group refers to a phosphino group substituted by an alkyl group. The number of carbon atoms of the alkyl phosphino group is not particularly limited, but preferably 1 to 20. Examples of the alkyl phosphino group include dimethyl phosphino, diethyl phosphino, di-n-propyl phosphino, diisopropyl phosphino, di-n-butyl phosphino, di-sec-butyl phosphino, di-tert-butyl phosphino, diisobutyl phosphino, tert-butyl isopropyl phosphino, di-n-hexyl phosphino, di-n-octyl phosphino, di-n-methyl phosphino, etc., but are not limited thereto. The aryl phosphino group refers to a phosphino group substituted by an aryl group. The number of carbon atoms of the aryl phosphino group is not particularly limited, but preferably 6 to 30. Examples of the aryl phosphino group include diphenyl phosphino, dibenzyl phosphino, methylphenyl phosphino, benzylhexyl phosphino, bistrimethylsilyl phosphino, etc., but are not limited thereto.

在本说明书中,阴离子性基团与化学式1的结构具有化学键,上述化学键可以是指离子键。上述阴离子性基团没有特别限定,例如可以适用美国专利第7,939,644号、日本特开第2006-003080号、日本特开第2006-001917号、日本特开第2005-159926号、日本特开第2007-7028897号、日本特开第2005-071680号、韩国申请公开第2007-7000693号、日本特开第2005-111696号、日本特开第2008-249663号、日本特开第2014-199436中记载的阴离子。In this specification, the anionic group has a chemical bond with the structure of Chemical Formula 1, and the chemical bond may refer to an ionic bond. The anionic group is not particularly limited, and for example, anions described in U.S. Patent No. 7,939,644, Japanese Patent Application No. 2006-003080, Japanese Patent Application No. 2006-001917, Japanese Patent Application No. 2005-159926, Japanese Patent Application No. 2007-7028897, Japanese Patent Application No. 2005-071680, Korean Application Publication No. 2007-7000693, Japanese Patent Application No. 2005-111696, Japanese Patent Application No. 2008-249663, and Japanese Patent Application No. 2014-199436 may be applied.

作为上述阴离子性基团的具体例子,有三氟甲磺酸根阴离子、双(三氟甲基磺酰基)酰胺阴离子、双三氟甲烷磺酰亚胺阴离子、双全氟乙基磺酰亚胺阴离子、四苯基硼酸盐阴离子、四(4-氟苯基)硼酸盐阴离子、四(五氟苯基)硼酸盐阴离子、三(三氟甲烷磺酰基)甲基化阴离子、SO3 -、CO2 -、SO2N-SO2CF3、SO2N-SO2CF2CF3、卤素基团、例如氟基团、碘基团、氯基团等,但不仅限于此。Specific examples of the above-mentioned anionic groups include trifluoromethanesulfonate anion, bis(trifluoromethylsulfonyl)amide anion, bistrifluoromethanesulfonimide anion, bisperfluoroethylsulfonimide anion, tetraphenylborate anion, tetrakis(4-fluorophenyl)borate anion, tetrakis(pentafluorophenyl)borate anion, tris(trifluoromethanesulfonyl)methyl anion, SO 3 - , CO 2 - , SO 2 N - SO 2 CF 3 , SO 2 N - SO 2 CF 2 CF 3 , halogen groups such as fluorine groups, iodine groups, chlorine groups, etc., but are not limited thereto.

本说明书中,阴离子性基团其本身可以具有阴离子,或者可以与其它阳离子一起以配位形态存在。因此,根据取代的阴离子性基团的个数,本发明的化合物分子整体电荷之和可能发生变化。例如,上述化学式1包含铵结构时,由于在上述一个铵结构中具有阳离子,因此分子整体电荷之和可以具有从取代的阴离子性基团的个数中减去1而得的值程度的阴离子至0的值。In this specification, anionic groups themselves may have anions, or may exist in coordination with other cations. Therefore, the sum of the overall charges of the compound molecules of the present invention may change depending on the number of substituted anionic groups. For example, when the above chemical formula 1 contains an ammonium structure, since there is a cation in the above one ammonium structure, the sum of the overall charges of the molecule may have a value of anions to 0, which is a value obtained by subtracting 1 from the number of substituted anionic groups.

本说明书中,上述烷氧基可以为直链或支链,碳原子数没有特别限定,但优选为1至30,具体可以为1至20,更具体可以为1至10。In the present specification, the alkoxy group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30, specifically 1 to 20, and more specifically 1 to 10.

本说明书中,上述烷基可以为直链或支链,碳原子数没有特别限定,但优选为1至60。根据一实施方式,上述烷基的碳原子数为1至30。根据另一实施方式,上述烷基的碳原子数为1至20。根据另一实施方式,上述烷基的碳原子数为1至10。作为烷基的具体例子,有甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、正己基、正庚基、正辛基等,但并不限定于此。本说明书中,环烷基没有特别限定,但优选为碳原子数3至30的环烷基,特别优选为环戊基、环己基,但并不限定于此。In the present specification, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, etc., but are not limited thereto. In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, and particularly preferably a cyclopentyl group and a cyclohexyl group, but are not limited thereto.

本说明书中,环烷基没有特别限定,但优选为碳原子数3至60的环烷基,根据一实施方式,上述环烷基的碳原子数为3至30。根据另一实施方式,上述环烷基的碳原子数为3至20。根据另一实施方式,上述环烷基的碳原子数为3至6。具体而言,有环丙基、环丁基、环戊基、环己基、环庚基、环辛基等,但并不限定于此。In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

本说明书中,上述烯基可以为直链或支链,碳原子数没有特别限定,但优选为2至60。根据一实施方式,上述烯基的碳原子数为2至30。根据另一实施方式,上述烯基的碳原子数为2至20。根据另一实施方式,上述烯基的碳原子数为2至10。作为烯基的具体例子,优选茋基(stylbenyl)、苯乙烯基(styrenyl)等芳基被取代的烯基,但并不限定于此。In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 30. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. As specific examples of the alkenyl group, an alkenyl group in which an aryl group is substituted, such as a stylbenyl group and a styrenyl group, is preferred, but not limited thereto.

本说明书中,环烯基没有特别限定,但优选为碳原子数3至60的环烯基,根据一实施方式,上述环烯基的碳原子数为3至30。根据另一实施方式,上述环烯基的碳原子数为3至20。根据另一实施方式,上述环烯基的碳原子数为3至6。作为环烯基的例子,优选为环戊烯基、环己烯基,但并不限定于此。In the present specification, the cycloalkenyl group is not particularly limited, but is preferably a cycloalkenyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkenyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkenyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkenyl group has 3 to 6 carbon atoms. Examples of the cycloalkenyl group include, but are not limited to, cyclopentenyl and cyclohexenyl.

本说明书中,芳基没有特别限定,但优选为碳原子数6至60的芳基,可以为单环芳基或多环芳基。根据一实施方式,上述芳基的碳原子数为6至30。根据一实施方式,上述芳基的碳原子数为6至20。关于上述芳基,作为单环芳基,可以为苯基、联苯基、三联苯基等,但并不限定于此。作为上述多环芳基,可以为萘基、蒽基、茚基、菲基、芘基、苝基、三苯基、基、芴基等,但并不限定于此。In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, etc., but it is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, indenyl, phenanthrenyl, pyrenyl, perylenyl, triphenyl, yl, fluorenyl, etc., but are not limited to these.

本说明书中,芴基可以被取代,2个取代基可以彼此结合而形成螺结构。In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

在上述芴基被取代的情况下,可以成为等螺芴基、(9,9-二甲基芴基)和(9,9-二苯基芴基)等被取代的芴基。但并不限定于此。In the case where the above fluorenyl group is substituted, it can be Spirofluorenyl, (9,9-dimethylfluorenyl) and (9,9-diphenylfluorenyl) and the like substituted fluorenyl, but the present invention is not limited thereto.

本说明书中,具体而言,上述芳烷基的芳基部分的碳原子数可以为6至30,烷基部分的碳原子数可以为1至30。作为具体例子,有苄基、对甲基苄基、间甲基苄基、对乙基苄基、间乙基苄基、3,5-二甲基苄基、α-甲基苄基、α,α-二甲基苄基、α,α-甲基苯基苄基、1-萘基苄基、2-萘基苄基、对氟苄基、3,5-二氟苄基、α,α-双三氟甲基苄基、对甲氧基苄基、间甲氧基苄基、α-苯氧基苄基、α-苄氧基苄基、萘基甲基、萘基乙基、萘基异丙基、吡咯基甲基、吡咯基乙基、氨基苄基、硝基苄基、氰基苄基、1-羟基-2-苯基异丙基、1-氯-2-苯基异丙基等,但并不限定于此。In the present specification, specifically, the number of carbon atoms of the aryl part of the aralkyl group may be 6 to 30, and the number of carbon atoms of the alkyl part may be 1 to 30. Specific examples include benzyl, p-methylbenzyl, m-methylbenzyl, p-ethylbenzyl, m-ethylbenzyl, 3,5-dimethylbenzyl, α-methylbenzyl, α,α-dimethylbenzyl, α,α-methylphenylbenzyl, 1-naphthylbenzyl, 2-naphthylbenzyl, p-fluorobenzyl, 3,5-difluorobenzyl, α,α-bistrifluoromethylbenzyl, p-methoxybenzyl, m-methoxybenzyl, α-phenoxybenzyl, α-benzyloxybenzyl, naphthylmethyl, naphthylethyl, naphthylisopropyl, pyrrolylmethyl, pyrrolylethyl, aminobenzyl, nitrobenzyl, cyanobenzyl, 1-hydroxy-2-phenylisopropyl, 1-chloro-2-phenylisopropyl, and the like, but the present invention is not limited thereto.

本说明书中,上述杂环基是包含O、N或S作为杂原子的杂环基,碳原子数没有特别限定,但碳原子数为2至30,具体而言,碳原子数为2至20。作为杂环基的例子,有噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、唑基、二唑基、三唑基、吡啶基、联吡啶基、三嗪基、吖啶基、哒嗪基、喹啉基、异喹啉基、吲哚基、咔唑基、苯并唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、苯并呋喃基、二苯并呋喃基等,但不仅限于此。In the present specification, the heterocyclic group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but the number of carbon atoms is 2 to 30, specifically, the number of carbon atoms is 2 to 20. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, triazine, acridinyl, pyridazinyl, quinolyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, dibenzofuranyl, etc., but are not limited thereto.

本说明书中,杂芳基为芳香族,除此以外,可以适用上述的关于杂环基的说明。In the present specification, a heteroaryl group is aromatic, and other than this, the above description about the heterocyclic group is applicable.

本说明书中,甲硅烷基可以由–SiZ1Z2Z3的化学式表示,上述Z1、Z2和Z3各自可以为氢、取代或未取代的烷基、或者取代或未取代的芳基。上述甲硅烷基具体有三甲基甲硅烷基(TMS)、三乙基甲硅烷基、叔丁基二甲基甲硅烷基、乙烯基二甲基甲硅烷基、丙基二甲基甲硅烷基、三苯基甲硅烷基、二苯基甲硅烷基、苯基甲硅烷基等,但并不限定于此。In the present specification, the silyl group can be represented by the chemical formula -SiZ1Z2Z3, and the above Z1, Z2 and Z3 can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The above silyl group specifically includes trimethylsilyl (TMS), triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but is not limited thereto.

本说明书中,作为烷基磺酰基(Alkyl sulfoxy),有甲基磺酰基、乙基磺酰基、丙基磺酰基、丁基磺酰基等,但并不限定于此。上述烷基磺酰基中的烷基可以适用上述关于烷基的说明。In this specification, the alkylsulfonyl group ( The alkylsulfoxy group includes methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl and the like, but is not limited thereto. The alkyl group in the alkylsulfonyl group may be the same as the above description of the alkyl group.

本说明书中,硼基可以由-BW4W5的化学式表示,上述W4和W5各自可以为氢、取代或未取代的烷基、或者取代或未取代的芳基。上述硼基具体有三甲基硼基、三乙基硼基、叔丁基二甲基硼基、三苯基硼基、苯基硼基等,但并不限定于此。In the present specification, the boryl group can be represented by the chemical formula -BW4W5, wherein W4 and W5 can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The boryl group specifically includes trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, etc., but is not limited thereto.

本说明书中,丙烯酰基是指光聚合性不饱和基团,例如,可以举出(甲基)丙烯酰基,但并不限定于此。In the present specification, the acryloyl group refers to a photopolymerizable unsaturated group, and examples thereof include a (meth)acryloyl group, but the present invention is not limited thereto.

本说明书中,丙烯酸酯基是指光聚合性不饱和基团,例如,可以举出(甲基)丙烯酸酯基,但并不限定于此。In the present specification, the acrylate group refers to a photopolymerizable unsaturated group, and examples thereof include a (meth)acrylate group, but the present invention is not limited thereto.

本说明书中,“(甲基)丙烯酰基”是指选自丙烯酰基和甲基丙烯酰基中的至少一种。“(甲基)丙烯酸酯”的标记也具有相同的意思。In the present specification, "(meth)acryloyl" means at least one selected from acryloyl and methacryloyl. The term "(meth)acrylate" also has the same meaning.

本说明书中,醚基可以由-COR表示。上述R为取代或未取代的烷基。上述烷基可以适用上述烷基的说明。In the present specification, the ether group can be represented by -COR. The above R is a substituted or unsubstituted alkyl group. The above description of the alkyl group can be applied to the above alkyl group.

本说明书中,磺酸酯/盐基可以为烷基磺酸酯/盐基或芳基磺酸酯/盐基。上述“烷基”可以适用上述关于烷基的说明,上述“芳基”可以适用上述关于芳基的说明。In the present specification, the sulfonate group may be an alkylsulfonate group or an arylsulfonate group. The above description on the alkyl group can be applied to the above "alkyl group", and the above description on the aryl group can be applied to the above "aryl group".

本说明书中,胺基可以选自-NH2、烷基胺基、N-烷基芳基胺基、芳基胺基、N-芳基杂芳基胺基、N-烷基杂芳基胺基和杂芳基胺基,碳原子数没有特别限定,但优选为1至30。作为胺基的具体例子,有甲基胺基、二甲基胺基、乙基胺基、二乙基胺基、苯基胺基、萘基胺基、联苯基胺基、蒽基胺基、9-甲基-蒽基胺基、二苯基胺基、N-苯基萘基胺基、二甲苯基胺基、N-苯基甲苯基胺基、三苯基胺基、N-苯基联苯基胺基、N-苯基萘基胺基、N-联苯基萘基胺基、N-萘基芴基胺基、N-苯基菲基胺基、N-联苯基菲基胺基、N-苯基芴基胺基、N-苯基三联苯基胺基、N-菲基芴基胺基、N-联苯基芴基胺基等,但并不限定于此。In the present specification, the amine group may be selected from -NH 2 , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but preferably 1 to 30. Specific examples of amino groups include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthrylamino, 9-methyl-anthrylamino, diphenylamino, N-phenylnaphthylamino, xylylamino, N-phenyltolylamino, triphenylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrenylamino, N-biphenylphenanthrenylamino, N-phenylfluorenylamino, N-phenylterphenylamino, N-phenanthrenylfluorenylamino, and N-biphenylfluorenylamino.

本说明书中,含有氮原子的二酐基团的碳原子数没有特别限定,但可以为4至30,具体地可以为4至20,更具体地可以为4至15。In the present specification, the number of carbon atoms of the dianhydride group containing a nitrogen atom is not particularly limited, but may be 4 to 30, specifically 4 to 20, and more specifically 4 to 15.

本说明书中,亚烷基是指烷烃(alkane)上有两个结合位置的基团。上述亚烷基可以为直链、支链或环状。亚烷基的碳原子数没有特别限定,例如,碳原子数为1至30,具体为1至20,更具体为1至10。In this specification, an alkylene group refers to a group having two binding positions on an alkane. The alkylene group may be linear, branched or cyclic. The number of carbon atoms in the alkylene group is not particularly limited, for example, the number of carbon atoms is 1 to 30, specifically 1 to 20, and more specifically 1 to 10.

本说明书中,亚杂烷基是指包含O、N或S作为杂原子的烷烃(alkane)上有两个结合位置的基团。上述亚杂烷基可以为直链、支链或环状。亚杂烷基的碳原子数没有特别限定,例如碳原子数为2至30,具体地碳原子数为2至20,更具体地碳原子为数2至10。In this specification, heteroalkylene refers to a group having two binding positions on an alkane containing O, N or S as a heteroatom. The above heteroalkylene may be linear, branched or cyclic. The number of carbon atoms in the heteroalkylene is not particularly limited, for example, the number of carbon atoms is 2 to 30, specifically the number of carbon atoms is 2 to 20, and more specifically the number of carbon atoms is 2 to 10.

本说明书中,亚芳基是指在芳基上有两个结合位置的基团,即2价基团。它们除了各自为2价基团以外,可以适用上述芳基的说明。In the present specification, an arylene group refers to a group having two bonding positions on an aryl group, that is, a divalent group. The above description of the aryl group is applicable to these groups except that they are each a divalent group.

本说明书中,亚杂芳基是指在杂芳基上有两个结合位置的基团,即2价基团。它们除了各自为2价基团以外,可以适用上述杂芳基的说明。In the present specification, a heteroarylene group refers to a group having two bonding positions on a heteroaryl group, that is, a divalent group. Except that each of these groups is a divalent group, the above description of the heteroaryl group is applicable.

本说明书的一实施方式中,上述L1和L2彼此相同或不同,各自独立地为取代或未取代的直链或支链的亚烷基。In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a substituted or unsubstituted linear or branched alkylene group.

本说明书的一实施方式中,上述化学式1的L1和L2彼此相同或不同,各自独立地为碳原子数1至30的取代或未取代的直链或支链的亚烷基。In one embodiment of the present specification, L1 and L2 in the above Chemical Formula 1 are the same as or different from each other, and are each independently a substituted or unsubstituted linear or branched alkylene group having 1 to 30 carbon atoms.

本说明书的一实施方式中,上述化学式1的L1和L2彼此相同或不同,各自独立地为碳原子数1至20的取代或未取代的直链或支链的亚烷基。In one embodiment of the present specification, L1 and L2 in the above Chemical Formula 1 are the same as or different from each other, and are each independently a substituted or unsubstituted linear or branched alkylene group having 1 to 20 carbon atoms.

根据本说明书的一实施方式,上述化学式1的L1和L2彼此相同或不同,各自独立地为碳原子数1至10的取代或未取代的直链或支链的亚烷基。According to one embodiment of the present specification, L1 and L2 in the above Chemical Formula 1 are the same as or different from each other, and are each independently a substituted or unsubstituted linear or branched alkylene group having 1 to 10 carbon atoms.

本说明书的一实施方式中,上述化学式1的L1和L2彼此相同或不同,各自独立地为取代或未取代的亚甲基、取代或未取代的亚乙基、取代或未取代的亚丙基、或者取代或未取代的亚丁基。In one embodiment of the present specification, L1 and L2 in the above Chemical Formula 1 are the same as or different from each other, and are each independently a substituted or unsubstituted methylene group, a substituted or unsubstituted ethylene group, a substituted or unsubstituted propylene group, or a substituted or unsubstituted butylene group.

本说明书的一实施方式中,上述化学式1的L1和L2彼此相同或不同,各自独立地为亚甲基、亚乙基、亚丙基或亚丁基。In one embodiment of the present specification, L1 and L2 in the above Chemical Formula 1 are the same as or different from each other, and are each independently a methylene group, an ethylene group, a propylene group, or a butylene group.

本说明书的一实施方式中,上述化学式1的R1和R2彼此相同或不同,各自独立地为碳原子数4至30的含有氮原子的二酐基团。In one embodiment of the present specification, R1 and R2 in the above Chemical Formula 1 are the same as or different from each other, and are each independently a dianhydride group containing a nitrogen atom and having 4 to 30 carbon atoms.

本说明书的一实施方式中,上述化学式1的R1和R2彼此相同或不同,各自独立地为碳原子数4至20的含有氮原子的二酐基团。In one embodiment of the present specification, R1 and R2 in the above Chemical Formula 1 are the same as or different from each other, and are each independently a dianhydride group having 4 to 20 carbon atoms and containing a nitrogen atom.

本说明书的一实施方式中,上述化学式1的R1和R2彼此相同或不同,各自独立地为碳原子数4至15的含有氮原子的二酐基团。In one embodiment of the present specification, R1 and R2 in the above Chemical Formula 1 are the same as or different from each other, and are each independently a dianhydride group containing a nitrogen atom and having 4 to 15 carbon atoms.

本说明书的一实施方式中,上述含有氮原子的二酐基团可以由下述取代基中的任一个表示。In one embodiment of the present specification, the dianhydride group containing a nitrogen atom may be represented by any of the following substituents.

上述取代基中,表示与上述化学式1中的L1或L2连接的部位,In the above substituents, represents a site connected to L1 or L2 in the above chemical formula 1,

X1、X2和Y1至Y3彼此相同或不同,各自独立地为氢、氘、卤素基团、硝基、-OH、-SO3H、-COOH、膦基、阴离子性基团、取代或未取代的烷基、或者取代或未取代的芳基,或者相邻的基团结合而形成取代或未取代的环。X1, X2 and Y1 to Y3 are the same as or different from each other and are independently hydrogen, deuterium, a halogen group, a nitro group, -OH, -SO3H , -COOH, a phosphine group, an anionic group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or adjacent groups are combined to form a substituted or unsubstituted ring.

本说明书的一实施方式中,上述X1和X2可以彼此结合而形成取代或未取代的环。In one embodiment of the present specification, the above-mentioned X1 and X2 may be combined with each other to form a substituted or unsubstituted ring.

本说明书的一实施方式中,上述X1和X2可以彼此结合而形成取代或未取代的苯环、或者取代或未取代的萘环。In one embodiment of the present specification, X1 and X2 may be bonded to each other to form a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring.

本说明书的一实施方式中,上述X1和X2可以彼此结合而形成被-SO3M或-SO2NHY取代或未取代的苯环、或者被-SO3M或-SO2NHY取代或未取代的萘环,上述M和Y与上述化学式1中的定义相同。In one embodiment of the present specification, X1 and X2 may be combined to form a benzene ring substituted or unsubstituted by -SO 3 M or -SO 2 NHY, or a naphthalene ring substituted or unsubstituted by -SO 3 M or -SO 2 NHY, and M and Y are the same as defined in Chemical Formula 1.

本说明书的一实施方式中,上述X1和X2可以彼此结合而形成被-SO3M或-SO2NHY取代或未取代的苯环、或者被-SO3M或-SO2NHY取代或未取代的萘环,上述M选自氢、Na、K、Rb、Cs、Fr、以及包含铵结构的部分,上述Y为取代或未取代的烷基。In one embodiment of the present specification, X1 and X2 may be combined with each other to form a benzene ring which may be substituted by -SO3M or -SO2NHY , or a naphthalene ring which may be substituted by -SO3M or -SO2NHY , wherein M is selected from hydrogen, Na, K, Rb, Cs, Fr, and a moiety containing an ammonium structure, and Y is a substituted or unsubstituted alkyl group.

本说明书的一实施方式中,上述X1和X2可以彼此结合而形成被-SO3M或-SO2NHY取代或未取代的苯环、或者被-SO3M或-SO2NHY取代或未取代的萘环,上述M选自氢、Na、K、Rb、Cs、Fr、以及包含铵结构的部分,上述Y为取代或未取代的正己基。In one embodiment of the present specification, X1 and X2 may be combined with each other to form a benzene ring which may be substituted by -SO3M or -SO2NHY , or a naphthalene ring which may be substituted by -SO3M or -SO2NHY , wherein M is selected from hydrogen, Na, K, Rb, Cs, Fr, and a moiety containing an ammonium structure, and Y is a substituted or unsubstituted n-hexyl group.

本说明书的一实施方式中,上述X1和X2可以彼此结合而形成被-SO3M或-SO2NHY取代或未取代的苯环、或者被-SO3M或-SO2NHY取代或未取代的萘环,上述M选自氢、Na、K、Rb、Cs、Fr、以及包含铵结构的部分,上述Y为被乙基取代的正己基。In one embodiment of the present specification, X1 and X2 may be combined with each other to form a benzene ring which may be substituted by -SO3M or -SO2NHY , or a naphthalene ring which may be substituted by -SO3M or -SO2NHY , wherein M is selected from hydrogen, Na, K, Rb, Cs, Fr, and a moiety containing an ammonium structure, and Y is a n-hexyl group substituted by an ethyl group.

本说明书的一实施方式中,上述Y1和Y2、以及Y2和Y3可以结合而形成取代或未取代的环。In one embodiment of the present specification, the above-mentioned Y1 and Y2, and Y2 and Y3 may be combined to form a substituted or unsubstituted ring.

本说明书的一实施方式中,上述Y1和Y2、以及Y2和Y3可以结合而形成取代或未取代的苯环。In one embodiment of the present specification, the above-mentioned Y1 and Y2, and Y2 and Y3 may be combined to form a substituted or unsubstituted benzene ring.

本说明书的一实施方式中,上述Y1和Y2、以及Y2和Y3可以结合而形成被-SO3M或-SO2NHY取代或未取代的苯环,上述M和Y与上述化学式1中的定义相同。In one embodiment of the present specification, Y1 and Y2, and Y2 and Y3 may be combined to form a benzene ring which may be substituted or unsubstituted by -SO 3 M or -SO 2 NHY, and M and Y are the same as defined in the above Chemical Formula 1.

本说明书的一实施方式中,上述Y1和Y2、以及Y2和Y3可以结合而形成被-SO3M或-SO2NHY取代或未取代的苯环,上述M选自Na+、K+、Rb+、Cs+、Fr+、以及包含铵结构的部分,上述Y为取代或未取代的烷基。In one embodiment of the present specification, Y1 and Y2, and Y2 and Y3 may be combined to form a benzene ring substituted or unsubstituted by -SO 3 M or -SO 2 NHY, wherein M is selected from Na + , K + , Rb + , Cs + , Fr + , and a moiety containing an ammonium structure, and Y is a substituted or unsubstituted alkyl group.

本说明书的一实施方式中,上述Y1和Y2、以及Y2和Y3可以结合而形成被-SO3M或-SO2NHY取代或未取代的苯环,上述M选自Na+、K+、Rb+、Cs+、Fr+、以及包含铵结构的部分,上述Y为取代或未取代的正己基。In one embodiment of the present specification, Y1 and Y2, and Y2 and Y3 may be combined to form a benzene ring which is substituted or unsubstituted by -SO 3 M or -SO 2 NHY, wherein M is selected from Na + , K + , Rb + , Cs + , Fr + , and a moiety containing an ammonium structure, and Y is a substituted or unsubstituted n-hexyl group.

本说明书的一实施方式中,上述Y1和Y2、以及Y2和Y3可以结合而形成被-SO3M或-SO2NHY取代或未取代的苯环,上述M选自Na+、K+、Rb+、Cs+、Fr+、以及包含铵结构的部分,上述Y为被乙基取代的正己基。In one embodiment of the present specification, Y1 and Y2, and Y2 and Y3 may be combined to form a benzene ring which is substituted or unsubstituted by -SO 3 M or -SO 2 NHY, wherein M is selected from Na + , K + , Rb + , Cs + , Fr + , and a moiety containing an ammonium structure, and Y is a n-hexyl group substituted by an ethyl group.

本说明书的一实施方式中,上述含有氮原子的二酐基团可以由下述取代基中的任一个表示。In one embodiment of the present specification, the dianhydride group containing a nitrogen atom may be represented by any of the following substituents.

在上述取代基中,表示与上述化学式1中的L1或L2连接的部位,X3至X5和Y4彼此相同或不同,各自独立地为氢、氘、卤素基团、硝基、-OH、-SO3H、-SO3M、-SO2NHY、-COOH、膦基、阴离子性基团、取代或未取代的烷基、或者取代或未取代的芳基,上述M和Y与上述化学式1中的定义相同,x3为0至4的整数,x4、x5和y4为0至6的整数。In the above substituents, represents a site connected to L1 or L2 in the above Chemical Formula 1, X3 to X5 and Y4 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitro group, -OH, -SO3H , -SO3M , -SO2NHY , -COOH, a phosphino group, an anionic group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, the above M and Y are the same as defined in the above Chemical Formula 1, x3 is an integer from 0 to 4, and x4, x5 and y4 are integers from 0 to 6.

在上述取代基中,表示与上述化学式1中的L1或L2连接的部位,X3至X5和Y4彼此相同或不同,各自独立地为氢、-SO3M、或-SO2NHY,上述M和Y与上述化学式1中的定义相同,x3为0至4的整数,x4、x5和y4为0至6的整数。In the above substituents, represents a site connected to L1 or L2 in the above Chemical Formula 1, X3 to X5 and Y4 are the same as or different from each other and are independently hydrogen, -SO 3 M, or -SO 2 NHY, the above M and Y are the same as defined in the above Chemical Formula 1, x3 is an integer of 0 to 4, and x4, x5 and y4 are integers of 0 to 6.

本说明书的一实施方式中,上述化学式1的R3和R4彼此相同或不同,各自独立地为碳原子数1至30的取代或未取代的烷基、或者碳原子数6至30的取代或未取代的芳基。In one embodiment of the present specification, R3 and R4 in the above Chemical Formula 1 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

本说明书的一实施方式中,上述化学式1的R3和R4彼此相同或不同,各自独立地为碳原子数1至20的取代或未取代的烷基、或者碳原子数6至20的取代或未取代的芳基。In one embodiment of the present specification, R3 and R4 in the above Chemical Formula 1 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

本说明书的一实施方式中,上述化学式1的R3和R4彼此相同或不同,各自独立地为碳原子数1至10的取代或未取代的烷基、或者碳原子数6至20的取代或未取代的芳基。In one embodiment of the present specification, R3 and R4 in the above Chemical Formula 1 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

本说明书的一实施方式中,上述化学式1的R3和R4彼此相同或不同,各自独立地为取代或未取代的甲基、或者取代或未取代的苯基。In one embodiment of the present specification, R3 and R4 in the above Chemical Formula 1 are the same as or different from each other, and are independently a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group.

本说明书的一实施方式中,上述化学式1的R3和R4彼此相同或不同,各自独立地为甲基、被卤素基团取代的甲基、或苯基。In one embodiment of the present specification, R3 and R4 in the above Chemical Formula 1 are the same as or different from each other, and are independently a methyl group, a methyl group substituted by a halogen group, or a phenyl group.

本说明书的一实施方式中,上述化学式1的R3和R4彼此相同或不同,各自独立地为甲基、三氟甲基(-CF3)、或苯基。In one embodiment of the present specification, R3 and R4 in the above Chemical Formula 1 are the same as or different from each other, and are each independently a methyl group, a trifluoromethyl group (—CF 3 ), or a phenyl group.

本说明书的一实施方式中,上述化学式1的R5至R12彼此相同或不同,各自独立地选自氢、氘、卤素基团、硝基、羟基、-COR、-COOR、酰亚胺基、酰胺基、阴离子性基团、碳原子数1至30的取代或未取代的烷氧基、碳原子数1至30的取代或未取代的烷基、碳原子数3至30的取代或未取代的环烷基、碳原子数2至30的取代或未取代的烯基、碳原子数3至30的取代或未取代的环烯基、取代或未取代的磺酸盐基、碳原子数1至30的取代或未取代的胺基、碳原子数6至30的取代或未取代的芳基、以及碳原子数2至30的取代或未取代的杂芳基,In one embodiment of the present specification, R5 to R12 in the above Chemical Formula 1 are the same as or different from each other, and are independently selected from hydrogen, deuterium, a halogen group, a nitro group, a hydroxyl group, -COR, -COOR, an imide group, an amide group, an anionic group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, a substituted or unsubstituted sulfonate group, a substituted or unsubstituted amine group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

上述R为氢、碳原子数1至30的取代或未取代的烷基、碳原子数3至30的取代或未取代的环烷基、或者碳原子数6至30的取代或未取代的芳基。The above R is hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

本说明书的一实施方式中,上述化学式1的R5至R12彼此相同或不同,各自独立地选自氢、氘、卤素基团、-OH、-SO3H、-SO3M、-SO2NM1M2、-SO2NHY、-COOH、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的烯基、取代或未取代的环烯基、取代或未取代的芳基、以及取代或未取代的杂芳基,上述M选自Na+、K+、Rb+、Cs+、Fr+、以及包含铵结构的部分,上述M1、M2和Y彼此相同或不同,各自独立地选自取代或未取代的烷基、取代或未取代的芳基、以及取代或未取代的杂芳基。In one embodiment of the present specification, R5 to R12 in the above Chemical Formula 1 are the same as or different from each other, and are each independently selected from hydrogen, deuterium, a halogen group, -OH, -SO 3 H, -SO 3 M, -SO 2 NM1M2, -SO 2 NHY, -COOH, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; the above M is selected from Na + , K + , Rb + , Cs + , Fr + , and a portion including an ammonium structure; the above M1, M2 and Y are the same as or different from each other, and are each independently selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

本说明书的一实施方式中,上述化学式1的R5至R12彼此相同或不同,各自独立地为氢、-SO2NHY、或者取代或未取代的烷基,上述Y为取代或未取代的烷基。In one embodiment of the present specification, R5 to R12 in the above Chemical Formula 1 are the same as or different from each other, and are independently hydrogen, -SO 2 NHY, or a substituted or unsubstituted alkyl group, and the above Y is a substituted or unsubstituted alkyl group.

本说明书的一实施方式中,上述化学式1的R5至R12彼此相同或不同,各自独立地为氢、-SO2NHY、或者碳原子数1至30的取代或未取代的烷基,上述Y为碳原子数1至30的取代或未取代的烷基。In one embodiment of the present specification, R5 to R12 in the above Chemical Formula 1 are the same or different and are independently hydrogen, -SO 2 NHY, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and Y is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

本说明书的一实施方式中,上述化学式1的R5至R12彼此相同或不同,各自独立地为氢、-SO2NHY、或者碳原子数1至20的取代或未取代的烷基,上述Y为碳原子数1至20的取代或未取代的烷基。In one embodiment of the present specification, R5 to R12 in the above Chemical Formula 1 are the same or different and are independently hydrogen, -SO 2 NHY, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and Y is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

本说明书的一实施方式中,上述化学式1的R5至R12彼此相同或不同,各自独立地为氢、-SO2NHY、或者碳原子数1至10的取代或未取代的烷基,上述Y为碳原子数1至10的取代或未取代的烷基。In one embodiment of the present specification, R5 to R12 in the above Chemical Formula 1 are the same or different and are independently hydrogen, -SO 2 NHY, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and Y is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

本说明书的一实施方式中,上述化学式1的R5至R12彼此相同或不同,各自独立地为氢、-SO2NHY、或者取代或未取代的甲基,上述Y为取代或未取代的己基。In one embodiment of the present specification, R5 to R12 in the above Chemical Formula 1 are the same as or different from each other, and are independently hydrogen, -SO 2 NHY, or a substituted or unsubstituted methyl group, and the above Y is a substituted or unsubstituted hexyl group.

本说明书的一实施方式中,上述化学式1的R5至R12彼此相同或不同,各自独立地为氢、-SO2NHY、或者被卤素基团取代或未取代的甲基,上述Y为被乙基取代或未取代的己基。In one embodiment of the present specification, R5 to R12 in the above Chemical Formula 1 are the same or different and are independently hydrogen, -SO 2 NHY, or a methyl group substituted or unsubstituted by a halogen group, and the above Y is a hexyl group substituted or unsubstituted by an ethyl group.

本说明书的一实施方式中,上述化学式1的R5至R12彼此相同或不同,各自独立地为氢、-SO2NHY、或三氟甲基(-CF3),上述Y为被乙基取代的己基。In one embodiment of the present specification, R5 to R12 in the above Chemical Formula 1 are the same as or different from each other, and are independently hydrogen, -SO 2 NHY, or trifluoromethyl (-CF 3 ), and the above Y is a hexyl group substituted with an ethyl group.

本说明书的一实施方式中,上述化学式1的R5为氢或三氟甲基。In one embodiment of the present specification, R5 in the above Chemical Formula 1 is hydrogen or trifluoromethyl.

本说明书的一实施方式中,上述化学式1的R6为氢、-SO2NHY、或三氟甲基,上述Y为被乙基取代的己基。In one embodiment of the present specification, R6 in the above Chemical Formula 1 is hydrogen, -SO 2 NHY, or trifluoromethyl, and the above Y is a hexyl group substituted with an ethyl group.

本说明书的一实施方式中,上述化学式1的R7为氢。In one embodiment of the present specification, R7 in the above Chemical Formula 1 is hydrogen.

本说明书的一实施方式中,上述化学式1的R8为氢。In one embodiment of the present specification, R8 in the above Chemical Formula 1 is hydrogen.

本说明书的一实施方式中,上述化学式1的R9为氢。In one embodiment of the present specification, R9 in the above Chemical Formula 1 is hydrogen.

本说明书的一实施方式中,上述化学式1的R10为氢。In one embodiment of the present specification, R10 in the above Chemical Formula 1 is hydrogen.

本说明书的一实施方式中,上述化学式1的R11为氢。In one embodiment of the present specification, R11 in the above Chemical Formula 1 is hydrogen.

本说明书的一实施方式中,上述化学式1的R12为氢。In one embodiment of the present specification, R12 in the above Chemical Formula 1 is hydrogen.

另外,本说明书的一实施方式中,R13至R17彼此相同或不同,各自独立地为氢、氘、卤素基团、-OH、-SO3 -、-SO3H、-SO3M、-SO2NM1M2、-SO2NHY、-COOH、阴离子性基团、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的芳基、或者取代或未取代的杂芳基,上述M选自Na+、K+、Rb+、Cs+、Fr+、以及包含铵结构的部分,上述M1、M2和Y彼此相同或不同,各自独立地选自取代或未取代的烷基、取代或未取代的芳基、以及取代或未取代的杂芳基,上述R13至R17中的至少一个为阴离子性基团。In addition, in one embodiment of the present specification, R13 to R17 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, -OH, -SO 3 - , -SO 3 H, -SO 3 M, -SO 2 NM1M2, -SO 2 NHY, -COOH, an anionic group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, the above M is selected from Na + , K + , Rb + , Cs + , Fr + , and a portion containing an ammonium structure, the above M1, M2 and Y are the same as or different from each other, and are each independently selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group, and at least one of the above R13 to R17 is an anionic group.

本书明书的一实施方式中,R13至R17彼此相同或不同,各自独立地为氢、-SO3 -、-SO3M或-SO2NHY,上述M和Y与上述定义的相同,上述R13至R17中的至少一个为阴离子性基团。In one embodiment of the present invention, R13 to R17 are the same as or different from each other, and are independently hydrogen, -SO 3 - , -SO 3 M or -SO 2 NHY, and the above M and Y are the same as defined above, and at least one of the above R13 to R17 is an anionic group.

本书明书的一实施方式中,R13至R17彼此相同或不同,各自独立地为氢、-SO3 -、-SO3M、或-SO2NHY,上述M和Y与上述定义的相同,上述R13至R17中的至少一个为-SO3 -In one embodiment of the present invention, R13 to R17 are the same as or different from each other, and are independently hydrogen, -SO 3 - , -SO 3 M, or -SO 2 NHY, wherein M and Y are the same as defined above, and at least one of R13 to R17 is -SO 3 - .

本书明书的一实施方式中,R13为-SO3 -In one embodiment of the present invention, R13 is -SO 3 - .

本书明书的一实施方式中,R4为氢。In one embodiment of the present invention, R4 is hydrogen.

本书明书的一实施方式中,R15为氢、-SO3M或-SO2NHY,上述M和Y与上述定义相同。In one embodiment of the present invention, R15 is hydrogen, -SO 3 M or -SO 2 NHY, and the above M and Y are the same as defined above.

本书明书的一实施方式中,R16为氢。In one embodiment of the present invention, R16 is hydrogen.

本书明书的一实施方式中,R17为氢。In one embodiment of the present invention, R17 is hydrogen.

本书明书的一实施方式中,X为阴离子性基团。In one embodiment of the present invention, X is an anionic group.

本书明书的一实施方式中,X选自含有从钨、钼、硅和磷中选择的至少一种元素和氧的化合物的阴离子;三氟甲磺酸根阴离子;双(三氟甲基磺酰基)酰胺阴离子;双三氟甲烷磺酰亚胺阴离子;双全氟乙基磺酰亚胺阴离子;四苯基硼酸盐阴离子;四(4-氟苯基)硼酸盐阴离子;四(五氟苯基)硼酸盐阴离子;三(三氟甲烷磺酰基)甲基化阴离子;以及卤素基团。In one embodiment of the present invention, X is selected from anions of compounds containing at least one element selected from tungsten, molybdenum, silicon and phosphorus and oxygen; trifluoromethanesulfonate anions; bis(trifluoromethylsulfonyl)amide anions; bistrifluoromethanesulfonyl imide anions; bisperfluoroethylsulfonyl imide anions; tetraphenylborate anions; tetrakis(4-fluorophenyl)borate anions; tetrakis(pentafluorophenyl)borate anions; tris(trifluoromethanesulfonyl)methylated anions; and halogen groups.

本说明书的一实施方式中,X可以为SO3 -In one embodiment of the present specification, X may be SO 3 - .

另外,本说明书的一实施方式中,r5和r6为0至4的整数,r5为2以上时,R5彼此相同或不同,r6为2以上时,R6彼此相同或不同。In one embodiment of the present specification, r5 and r6 are integers of 0 to 4, and when r5 is 2 or more, R5s are the same or different from each other, and when r6 is 2 or more, R6s are the same or different from each other.

本说明书的一实施方式中,r5和r6为0至3的整数,r5为2以上时,R5彼此相同或不同,r6为2以上时,R6彼此相同或不同。In one embodiment of the present specification, r5 and r6 are integers of 0 to 3, and when r5 is 2 or more, R5 are the same or different from each other, and when r6 is 2 or more, R6 are the same or different from each other.

本说明书的一实施方式中,r5和r6为0至2的整数,r5为2以上时,R5彼此相同或不同,r6为2时,R6彼此相同或不同。In one embodiment of the present specification, r5 and r6 are integers of 0 to 2, and when r5 is 2 or more, R5 are the same or different from each other, and when r6 is 2, R6 are the same or different from each other.

本说明书的一实施方式中,r5和r6为0或1。In one embodiment of the present specification, r5 and r6 are 0 or 1.

本说明书的一实施方式中,r5和r6为0。In one embodiment of the present specification, r5 and r6 are 0.

本说明书的一实施方式中,r5和r6为1。In one embodiment of the present specification, r5 and r6 are 1.

本说明书的一实施方式中,上述化学式1可以由下述结构表示,下述结构表示上述化学式1的异构体,上述化学式1表示代表结构。异构体是指分子式相同,但具有彼此不同的物理/化学性质的分子。In one embodiment of the present specification, the chemical formula 1 may be represented by the following structure, which represents an isomer of the chemical formula 1, and the chemical formula 1 represents a representative structure. Isomers are molecules having the same molecular formula but different physical/chemical properties.

在上述结构中,L1、L2、R1至R17、X、a、r5和r6与上述化学式1中的定义相同。In the above structure, L1, L2, R1 to R17, X, a, r5 and r6 are the same as defined in the above Chemical Formula 1.

关于上述异构体的说明可以适用于本说明书中的记载的全部呫吨系染料结构中。The above description on isomers is applicable to all xanthene dye structures described in this specification.

本说明书的一实施方式中,上述-SO3M可以表示-SO3 -和M离子结合或盐结合。In one embodiment of the present specification, the above-mentioned -SO 3 M may represent an ion bond or a salt bond of -SO 3 - and M.

本说明书的一实施方式中,上述M选自Na+、K+、Rb+、Cs+、Fr+、以及包含铵结构的部分,上述包含铵结构的部分可以包含由下述化学式A表示或由下述化学式B表示的单元。In one embodiment of the present specification, the M is selected from Na + , K + , Rb + , Cs + , Fr + , and a portion containing an ammonium structure. The portion containing an ammonium structure may include a unit represented by the following chemical formula A or the following chemical formula B.

[化学式A][Chemical formula A]

[化学式B][Chemical formula B]

在上述化学式A中,In the above chemical formula A,

Ra至Rd彼此相同或不同,各自独立地为氢、取代或未取代的烷基、取代或未取代的烯基、取代或未取代的芳基、取代或未取代的芳烷基、-L1-NHCO-R、或-L2-OCO-R,或者Ra至Rd中的两个彼此结合而形成取代或未取代的环,上述R为氢、取代或未取代的烷基、取代或未取代的芳基、或者取代或未取代的芳烷基,上述L1和L2为取代或未取代的亚烷基,Ra to Rd are the same as or different from each other, and are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl, -L 1 -NHCO-R, or -L 2 -OCO-R, or two of Ra to Rd are combined with each other to form a substituted or unsubstituted ring, the above R is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted aralkyl, and the above L 1 and L 2 are substituted or unsubstituted alkylene,

在上述化学式B中,In the above chemical formula B,

Rb至Rd彼此相同或不同,各自独立地为氢、取代或未取代的烷基、取代或未取代的烯基、取代或未取代的芳基、或者取代或未取代的芳烷基,或者Rb至Rd中的两个彼此结合而形成取代或未取代的环,Z为取代或未取代的亚烷基、取代或未取代的亚芳基、-L3-NHCO-、或-L4-OCO-,上述L3和L4为取代或未取代的亚烷基,Re至Rg彼此相同或不同,各自独立地为氢、或者取代或未取代的烷基。Rb to Rd are the same as or different from each other, and are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, or substituted or unsubstituted aralkyl, or two of Rb to Rd are combined with each other to form a substituted or unsubstituted ring, Z is substituted or unsubstituted alkylene, substituted or unsubstituted arylene, -L 3 -NHCO-, or -L 4 -OCO-, L 3 and L 4 are substituted or unsubstituted alkylene, and Re to Rg are the same as or different from each other, and are each independently hydrogen, or substituted or unsubstituted alkyl.

根据本说明书的一实施方式,在上述化学式A中,Ra至Rd彼此相同或不同,各自独立地为氢、碳原子数1至30的取代或未取代的烷基、碳原子数1至30的取代或未取代的烯基、碳原子数6至30的取代或未取代的芳基、碳原子数6至30的取代或未取代的芳烷基、-L1-NHCO-R、或-L2-OCO-R,或者Ra至Rd中的两个彼此结合而形成取代或未取代的环,上述R为氢、碳原子数1至30的取代或未取代的烷基、碳原子数6至30的取代或未取代的芳基、或者碳原子数6至30的取代或未取代的芳烷基,上述L1和L2为碳原子数1至30的取代或未取代的亚烷基,According to one embodiment of the present specification, in the above chemical formula A, Ra to Rd are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, -L 1 -NHCO-R, or -L 2 -OCO-R, or two of Ra to Rd are combined with each other to form a substituted or unsubstituted ring, the above R is hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, and the above L 1 and L 2 are substituted or unsubstituted alkylene groups having 1 to 30 carbon atoms,

在上述化学式B中,Rb至Rd彼此相同或不同,各自独立地为氢、碳原子数1至30的取代或未取代的烷基、碳原子数1至30的取代或未取代的烯基、碳原子数6至30的取代或未取代的芳基、或者碳原子数6至30的取代或未取代的芳烷基,或者Rb至Rd中的两个彼此结合而形成取代或未取代的环,Z为碳原子数1至30的取代或未取代的亚烷基、碳原子数6至30的取代或未取代的亚芳基、-L3-NHCO-、或-L4-OCO-,上述L3和L4为碳原子数1至30的取代或未取代的亚烷基,Re至Rg彼此相同或不同,各自独立地为氢、或者碳原子数1至30的取代或未取代的烷基。In the above chemical formula B, Rb to Rd are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, or two of Rb to Rd are combined with each other to form a substituted or unsubstituted ring, Z is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, -L 3 -NHCO-, or -L 4 -OCO-, L 3 and L 4 are substituted or unsubstituted alkylene groups having 1 to 30 carbon atoms, and Re to Rg are the same as or different from each other, and are each independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

根据本说明书的一实施方式,在上述化学式A中,Ra至Rd彼此相同或不同,各自独立地为氢、碳原子数1至20的取代或未取代的烷基、碳原子数1至20的取代或未取代的烯基、碳原子数6至20的取代或未取代的芳基、碳原子数6至20的取代或未取代的芳烷基、-L1-NHCO-R、或-L2-OCO-R,或者Ra至Rd中的2个彼此结合而形成取代或未取代的环,上述R为氢、碳原子数1至20的取代或未取代的烷基、碳原子数6至20的取代或未取代的芳基、或者碳原子数6至20的取代或未取代的芳烷基,上述L1和L2为碳原子数1至20的取代或未取代的亚烷基,According to one embodiment of the present specification, in the chemical formula A, Ra to Rd are the same as or different from each other and are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 20 carbon atoms, -L 1 -NHCO-R, or -L 2 -OCO-R, or two of Ra to Rd are combined with each other to form a substituted or unsubstituted ring, R is hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted aralkyl group having 6 to 20 carbon atoms, L 1 and L 2 are substituted or unsubstituted alkylene groups having 1 to 20 carbon atoms,

在上述化学式B中,Rb至Rd彼此相同或不同,各自独立地为氢、碳原子数1至20的取代或未取代的烷基、碳原子数1至20的取代或未取代的烯基、碳原子数6至20的取代或未取代的芳基、或者碳原子数6至20的取代或未取代的芳烷基,或者Rb至Rd中的2个彼此结合而形成取代或未取代的环,Z为碳原子数1至20的取代或未取代的亚烷基、碳原子数6至20的取代或未取代的亚芳基、-L3-NHCO-、或-L4-OCO-,上述L3和L4为碳原子数1至20的取代或未取代的亚烷基,Re至Rg彼此相同或不同,各自独立地为氢、或者碳原子数1至20的取代或未取代的烷基。In the above chemical formula B, Rb to Rd are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted aralkyl group having 6 to 20 carbon atoms, or two of Rb to Rd are combined with each other to form a substituted or unsubstituted ring, Z is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, -L 3 -NHCO-, or -L 4 -OCO-, L 3 and L 4 are substituted or unsubstituted alkylene groups having 1 to 20 carbon atoms, and Re to Rg are the same as or different from each other, and are each independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

本说明书的一实施方式中,上述单元是指单体包含在聚合物中的重复结构,上述单元可以包含在聚合物内的主链中来构成聚合物。In one embodiment of the present specification, the unit refers to a repeating structure of a monomer included in a polymer, and the unit may be included in a main chain in a polymer to constitute the polymer.

本说明书的一实施方式中,包含由上述化学式B表示的单元的化合物可以为高分子。In one embodiment of the present specification, the compound including the unit represented by the above Chemical Formula B may be a polymer.

在包含由上述化学式B表示的单元的化合物为高分子时,可以在1至500个的范围内包含由上述化学式B表示的单元。When the compound including the unit represented by the above Chemical Formula B is a polymer, the number of the unit represented by the above Chemical Formula B may be within a range of 1 to 500.

本说明书的一实施方式中,包含由上述化学式B表示的单元的化合物的重均分子量可以为1000至10000,优选为3000至8000,更优选为5000至7000。In one embodiment of the present specification, the weight average molecular weight of the compound including the unit represented by the above Chemical Formula B may be 1,000 to 10,000, preferably 3,000 to 8,000, and more preferably 5,000 to 7,000.

根据本说明书的一实施方式,包含由上述化学式B表示的单元的化合物的末端可以为氢、卤素基团、或者取代或未取代的烷基。According to one embodiment of the present specification, the terminal of the compound including the unit represented by the above Chemical Formula B may be hydrogen, a halogen group, or a substituted or unsubstituted alkyl group.

本说明书的一实施方式中,上述化学式1可以由下述化学式2表示。In one embodiment of the present specification, the above Chemical Formula 1 can be represented by the following Chemical Formula 2.

[化学式2][Chemical formula 2]

在上述化学式2中,In the above chemical formula 2,

L1、L2、R1至R17、X、a、r5和r6与上述化学式1中的定义相同。L1, L2, R1 to R17, X, a, r5 and r6 are the same as defined in the above Chemical Formula 1.

本说明书的一实施方式中,上述化学式1可以由下述化学式3表示。In one embodiment of the present specification, the above Chemical Formula 1 can be represented by the following Chemical Formula 3.

[化学式3][Chemical formula 3]

在上述化学式3中,In the above chemical formula 3,

L1、L2、R1至R17、X、a、r5和r6与上述化学式1中的定义相同。L1, L2, R1 to R17, X, a, r5 and r6 are the same as defined in the above Chemical Formula 1.

本说明书的一实施方式中,上述化学式1可以由下述化学式4表示。In one embodiment of the present specification, the above Chemical Formula 1 can be represented by the following Chemical Formula 4.

[化学式4][Chemical formula 4]

在上述化学式4中,In the above chemical formula 4,

L1、L2、R1至R17、X、a、r5和r6与上述化学式1中的定义相同。L1, L2, R1 to R17, X, a, r5 and r6 are the same as defined in the above Chemical Formula 1.

本说明书的一实施方式中,上述化学式1的含有氮原子的二酐基团可以是由下述取代基中的任一个表示的化合物。In one embodiment of the present specification, the dianhydride group containing a nitrogen atom of the above Chemical Formula 1 may be a compound represented by any of the following substituents.

在上述取代基中,表示与上述化学式1中的L1或L2连接的部位,In the above substituents, represents a site connected to L1 or L2 in the above chemical formula 1,

X1、X2、Y1至Y3彼此相同或不同,各自独立地为氢、氘、卤素基团、硝基、-OH、-SO3H、-COOH、膦基、阴离子性基团、取代或未取代的烷基、或者取代或未取代的芳基,或者相邻的基团可以结合而形成取代或未取代的环。X1, X2, Y1 to Y3 are the same as or different from each other and are independently hydrogen, deuterium, a halogen group, a nitro group, -OH, -SO3H , -COOH, a phosphine group, an anionic group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or adjacent groups may be combined to form a substituted or unsubstituted ring.

本说明书的一实施方式中,由上述化学式1表示的化合物可以由下述化学式中的任一个表示。In one embodiment of the present specification, the compound represented by the above Chemical Formula 1 may be represented by any of the following Chemical Formulas.

在上述化学式中,M和Y与上述化学式1中的定义相同。In the above chemical formula, M and Y are the same as defined in the above chemical formula 1.

本说明书的一实施方式中,上述化学式的环中没有指定取代位置的取代基表示可以取代于包含在环中的碳的任意部分。In one embodiment of the present specification, a substituent without specifying a substitution position in a ring of the above chemical formula means that it can be substituted on any part of carbon contained in the ring.

中,表示在被-CF3取代的苯环中,除了被-SCH3取代的碳以外,可以在其余碳中的任意一个上被取代,具体而言,可以由下述4个结构表示。exist middle, It means that in the benzene ring substituted with -CF 3 , except for the carbon substituted with -SCH 3 , any of the remaining carbons may be substituted. Specifically, it can be represented by the following four structures.

作为另一个示例,在中,表示在被-SO2NHY取代的萘环中,可以在包含于萘的碳中的任意一个上被取代,具体而言,可以由下述6个结构表示。As another example, in middle, It means that in the naphthalene ring substituted with -SO 2 NHY, substitution may be performed on any of the carbon atoms contained in naphthalene. Specifically, it can be represented by the following six structures.

在上述6个结构中,Y与上述定义的相同。In the above 6 structures, Y is the same as defined above.

另外,根据本说明书的一实施方式,可以提供包含上述化合物的色料组合物。Furthermore, according to one embodiment of the present specification, a coloring material composition including the above-mentioned compound can be provided.

上述色料组合物除了上述化学式1的化合物以外,还可以包含染料和颜料中的至少1种。例如,上述色料组合物可以只包含上述化学式1的化合物,但也可以包含上述化学式1的化合物和1种以上的染料,或者包含上述化学式1的化合物和1种以上的颜料,或者包含上述化学式1的化合物、1种以上的染料和1种以上的颜料。The colorant composition may further include at least one of a dye and a pigment in addition to the compound of the chemical formula 1. For example, the colorant composition may include only the compound of the chemical formula 1, but may also include the compound of the chemical formula 1 and one or more dyes, or include the compound of the chemical formula 1 and one or more pigments, or include the compound of the chemical formula 1, one or more dyes, and one or more pigments.

根据本说明书的一实施方式,可以提供包含上述色料组合物的感光性树脂组合物。According to one embodiment of the present specification, a photosensitive resin composition including the colorant composition can be provided.

根据本说明书的一实施方式,上述感光性树脂组合物还可以包含由上述化学式1表示的化合物、粘合剂树脂、多官能性单体、光聚合引发剂、以及溶剂。According to one embodiment of the present specification, the photosensitive resin composition may further include the compound represented by Chemical Formula 1, a binder resin, a multifunctional monomer, a photopolymerization initiator, and a solvent.

上述粘合剂树脂只要能够显示出由感光性树脂组合物制造的膜的强度、显影性等物性,则没有特别限定。The binder resin is not particularly limited as long as it can exhibit physical properties such as strength and developability of a film produced from the photosensitive resin composition.

上述粘合剂树脂可以利用赋予机械强度的多官能性单体和赋予碱溶性的单体的共聚树脂,还可以包含该技术领域中通常使用的粘合剂。The binder resin may be a copolymer resin of a multifunctional monomer that imparts mechanical strength and a monomer that imparts alkali solubility, and may further include a binder commonly used in the technical field.

赋予上述膜的机械强度的多官能性单体可以为不饱和羧酸酯类、芳香族乙烯基类、不饱和醚类、不饱和酰亚胺类、以及酸酐中的任一种以上。The polyfunctional monomer that imparts mechanical strength to the film may be any one or more of unsaturated carboxylic acid esters, aromatic vinyls, unsaturated ethers, unsaturated imides, and acid anhydrides.

作为上述不饱和羧酸酯类的具体例子,可以选自(甲基)丙烯酸苄酯、(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸二甲基氨基乙酯、(甲基)丙烯酸异丁酯、(甲基)丙烯酸叔丁酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸异冰片酯、(甲基)丙烯酸乙基己酯、(甲基)丙烯酸2-苯氧基乙酯、(甲基)丙烯酸四氢糠基酯、(甲基)丙烯酸羟乙酯、(甲基)丙烯酸-2-羟丙基酯、(甲基)丙烯酸2-羟基-3-氯丙酯、(甲基)丙烯酸4-羟基丁酯、酰基辛氧基-2-羟基丙基(甲基)丙烯酸酯、(甲基)丙烯酸甘油酯、(甲基)丙烯酸2-甲氧基乙酯、(甲基)丙烯酸3-甲氧基丁酯、乙氧基乙二醇(甲基)丙烯酸酯、甲氧基三乙二醇(甲基)丙烯酸酯、甲氧基三丙二醇(甲基)丙烯酸酯、聚(乙二醇)甲醚(甲基)丙烯酸酯、苯氧基二乙二醇(甲基)丙烯酸酯、对壬基苯氧基聚乙二醇(甲基)丙烯酸酯、对壬基苯氧基聚丙二醇(甲基)丙烯酸酯、(甲基)丙烯酸缩水甘油酯、(甲基)丙烯酸四氟丙基酯、(甲基)丙烯酸1,1,1,3,3,3-六氟异丙酯、(甲基)丙烯酸八氟戊基酯、(甲基)丙烯酸十七氟癸基酯、三溴苯基(甲基)丙烯酸酯、(α-羟基甲基)丙烯酸甲酯、(α-羟基甲基)丙烯酸乙酯、(α-羟基甲基)丙烯酸丙酯和(α-羟基甲基)丙烯酸丁酯,但不仅限于此。Specific examples of the unsaturated carboxylic acid esters include benzyl (meth)acrylate, methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, ethylhexyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxy-3-chloropropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, octyloxy-2-hydroxypropyl (meth)acrylate, glyceryl (meth)acrylate, 2-methoxyethyl (meth)acrylate, 3-methoxyethyl (meth)acrylate, The invention also includes but is not limited to butyl (meth)acrylate, ethoxy ethylene glycol (meth)acrylate, methoxy triethylene glycol (meth)acrylate, methoxy tripropylene glycol (meth)acrylate, poly (ethylene glycol) methyl ether (meth)acrylate, phenoxy diethylene glycol (meth)acrylate, p-nonylphenoxy polyethylene glycol (meth)acrylate, p-nonylphenoxy polypropylene glycol (meth)acrylate, glycidyl (meth)acrylate, tetrafluoropropyl (meth)acrylate, 1,1,1,3,3,3-hexafluoroisopropyl (meth)acrylate, octafluoropentyl (meth)acrylate, heptadecafluorodecyl (meth)acrylate, tribromophenyl (meth)acrylate, methyl (α-hydroxymethyl)acrylate, ethyl (α-hydroxymethyl)acrylate, propyl (α-hydroxymethyl)acrylate and butyl (α-hydroxymethyl)acrylate.

作为上述芳香族乙烯基类的具体例子,可以选自苯乙烯、α-甲基苯乙烯、(邻、间、对)-乙烯基甲苯、(邻、间、对)-甲氧基苯乙烯、以及(邻、间、对)-氯苯乙烯,但不仅限于此。Specific examples of the aromatic vinyl groups include, but are not limited to, styrene, α-methylstyrene, (o-, m-, p-)-vinyltoluene, (o-, m-, p-)-methoxystyrene, and (o-, m-, p-)-chlorostyrene.

作为上述不饱和醚类的具体例子,可以选自乙烯基甲醚、乙烯基乙醚、以及烯丙基缩水甘油醚,但不仅限于此。Specific examples of the unsaturated ethers include vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether, but are not limited thereto.

作为上述不饱和酰亚胺类的具体例子,可以选自N-苯基马来酰亚胺、N-(4-氯苯基)马来酰亚胺、N-(4-羟基苯基)马来酰亚胺、以及N-环己基马来酰亚胺,但不仅限于此。Specific examples of the unsaturated imides include, but are not limited to, N-phenylmaleimide, N-(4-chlorophenyl)maleimide, N-(4-hydroxyphenyl)maleimide, and N-cyclohexylmaleimide.

作为上述酸酐,有马来酸酐、甲基马来酸酐、四氢化邻苯二甲酸酐等,但不仅限于此。Examples of the acid anhydride include maleic anhydride, methylmaleic anhydride, tetrahydrophthalic anhydride, and the like, but the acid anhydride is not limited thereto.

上述赋予碱溶性的单体只要包含酸基团,则没有特别限定,例如优选使用选自(甲基)丙烯酸、巴豆酸、衣康酸、马来酸、富马酸、单甲基马来酸、5-降冰片烯-2-羧酸、单(2-((甲基)丙烯酰氧基)乙基邻苯二甲酸酯、单-2-((甲基)丙烯酰氧基)乙基琥珀酸酯、ω-羧基聚己内酯单(甲基)丙烯酸酯中的一种以上,但不仅限于此。The above-mentioned monomer imparting alkali solubility is not particularly limited as long as it contains an acid group. For example, it is preferred to use one or more selected from (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethylmaleic acid, 5-norbornene-2-carboxylic acid, mono-(2-((meth)acryloyloxy)ethyl phthalate, mono-2-((meth)acryloyloxy)ethyl succinate, and ω-carboxy polycaprolactone mono(meth)acrylate, but is not limited thereto.

根据本说明书的一实施方式,上述粘合剂树脂的酸值为50至130KOHmg/g,重均分子量为1000至50000。According to one embodiment of the present specification, the binder resin has an acid value of 50 to 130 KOHmg/g and a weight average molecular weight of 1,000 to 50,000.

上述多官能性单体是起到通过光而形成光致抗蚀刻图像的作用的单体,具体而言,可以为选自甲基丙烯酸丙二醇酯、二季戊四醇六丙烯酸酯、二季戊四醇丙烯酸酯、新戊二醇二丙烯酸酯、1,6-己二醇二丙烯酸酯、四乙二醇甲基丙烯酸酯、双苯氧基乙醇二丙烯酸酯、三羟基乙基异氰尿酸酯三甲基丙烯酸酯、三甲基丙烷三甲基丙烯酸酯、二苯基季戊四醇六丙烯酸酯、季戊四醇三甲基丙烯酸酯、季戊四醇四甲基丙烯酸酯以及二季戊四醇六甲基丙烯酸酯中的一种或两种以上的混合物。The above-mentioned multifunctional monomer is a monomer that plays a role in forming a photoresist image through light. Specifically, it can be one selected from propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol diacrylate, 1,6-hexanediol diacrylate, tetraethylene glycol methacrylate, bisphenoxyethanol diacrylate, trihydroxyethyl isocyanurate trimethacrylate, trimethylolpropane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate, or a mixture of two or more thereof.

上述光聚合引发剂只要是通过光产生自由基而触发交联的引发剂,则没有特别限定,例如可以为选自苯乙酮系化合物、联咪唑系化合物、三嗪系化合物、以及肟系化合物中的一种以上。The photopolymerization initiator is not particularly limited as long as it generates radicals by light to trigger crosslinking, and may be, for example, one or more selected from acetophenone compounds, biimidazole compounds, triazine compounds, and oxime compounds.

上述苯乙酮系化合物有2-羟基-2-甲基-1-苯基丙烷-1-酮、1-(4-异丙基苯基)-2-羟基-2-甲基丙烷-1-酮、4-(2-羟基乙氧基)-苯基-(2-羟基-2-丙基)酮、1-羟基环己基苯基甲酮、苯偶姻甲醚、苯偶姻乙醚、苯偶姻异丁醚、苯偶姻丁醚、2,2-二甲氧基-2-苯基苯乙酮、2-甲基-(4-甲基硫代)苯基-2-吗啉代-1-丙烷-1-酮、2-苄基-2-二甲基氨基-1-(4-吗啉代苯基)-丁烷-1-酮、2-(4-溴-苄基-2-二甲基氨基-1-(4-吗啉代苯基)-丁烷-1-酮或2-甲基-1-[4-(甲基硫代)苯基]-2-吗啉代丙烷-1-酮等,但并不限定于此。The above-mentioned acetophenone compounds include 2-hydroxy-2-methyl-1-phenylpropane-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropane-1-one, 4-(2-hydroxyethoxy)-phenyl-(2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl-(4-methylthio)phenyl-2-morpholino-1-propane-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butane-1-one, 2-(4-bromo-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butane-1-one or 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropane-1-one, but are not limited thereto.

作为上述联咪唑系化合物,有2,2-双(2-氯苯基)-4,4’,5,5’-四苯基联咪唑、2,2’-双(邻氯苯基)-4,4’,5,5’-四(3,4,5-三甲氧基苯基)-1,2’-联咪唑、2,2’-双(2,3-二氯苯基)-4,4’,5,5’-四苯基联咪唑、2,2’-双(邻氯苯基)-4,4,5,5’-四苯基-1,2’-联咪唑等,但并不限定于此。Examples of the biimidazole compounds include, but are not limited to, 2,2-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and 2,2'-bis(o-chlorophenyl)-4,4,5,5'-tetraphenyl-1,2'-biimidazole.

上述三嗪系化合物有3-{4-[2,4-双(三氯甲基)-均三嗪-6-基]苯硫基}丙酸、1,1,1,3,3,3-六氟异丙基-3-{4-[2,4-双(三氯甲基)-均三嗪-6-基]苯硫基}丙酸酯、乙基2-{4-[2,4-双(三氯甲基)-均三嗪-6-基]苯硫基}乙酸酯、2-环氧基乙基-2-{4-[2,4-双(三氯甲基)-均三嗪-6-基]苯硫基}乙酸酯、环己基-2-{4-[2,4-双(三氯甲基)-均三嗪-6-基]苯硫基}乙酸酯、苄基-2-{4-[2,4-双(三氯甲基)-均三嗪-6-基]苯硫基}乙酸酯、3-{氯-4-[2,4-双(三氯甲基)-均三嗪-6-基]苯硫基}丙酸、3-{4-[2,4-双(三氯甲基)-均三嗪-6-基]苯硫基}丙酰胺、2,4-双(三氯甲基)-6-对甲氧基苯乙烯基-均三嗪、2,4-双(三氯甲基)-6-(1-对二甲基氨基苯基)-1,3-丁二烯-均三嗪、2-三氯甲基-4-氨基-6-对甲氧基苯乙烯基-均三嗪等,但并不限定于此。The above triazine compounds include 3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propionic acid, 1,1,1,3,3,3-hexafluoroisopropyl-3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propionic acid, ethyl 2-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, 2-epoxyethyl-2-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, cyclohexyl-2-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate , benzyl-2-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}acetate, 3-{chloro-4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid, 3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionamide, 2,4-bis(trichloromethyl)-6-p-methoxyphenylvinyl-s-triazine, 2,4-bis(trichloromethyl)-6-(1-p-dimethylaminophenyl)-1,3-butadiene-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxyphenylvinyl-s-triazine, etc., but are not limited thereto.

上述肟系化合物有1-(4-苯硫基)苯基-1,2-辛二酮-2-(o-苯甲酰肟)(CIBA-GEIGY公司,CGI 124)、1-(9-乙基)-6-(2-甲基苯甲酰-3-基)-乙酮-1-(O-乙酰肟)(CGI 242)、N-1919(ADECA公司)等,但并不限定于此。The above-mentioned oxime compounds include 1-(4-phenylthio)phenyl-1,2-octanedione-2-(o-benzoyloxime) (CIBA-GEIGY, CGI 124), 1-(9-ethyl)-6-(2-methylbenzoyl-3-yl)-ethanone-1-(O-acetyloxime) (CGI 242), N-1919 (ADECA), etc., but are not limited to these.

上述溶剂可以为选自丙酮、甲基乙基酮、甲基异丁基酮、甲基溶纤剂、乙基溶纤剂、四氢呋喃、1,4-二烷、乙二醇二甲醚、乙二醇二乙醚、丙二醇二甲醚、丙二醇二乙醚、二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇甲基乙基醚、氯仿、二氯甲烷、1,2-二氯乙烷、1,1,1-三氯乙烷、1,1,2-三氯乙烷、1,1,2-三氯乙烯、己烷、庚烷、辛烷、环己烷、苯、甲苯、二甲苯、甲醇、乙醇、异丙醇、丙醇、丁醇、叔丁醇、2-乙氧基丙醇、2-甲氧基丙醇、3-甲氧基丁醇、环己酮、环戊酮、丙二醇甲醚乙酸酯、丙二醇乙醚乙酸酯、3-甲氧基丁基乙酸酯、3-乙氧基丙酸乙酯、乙基溶纤剂醋酸酯、甲基溶纤剂醋酸酯、乙酸丁酯、丙二醇单甲醚以及二丙二醇单甲醚中的一种以上,但不仅限于此。The solvent may be selected from acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dihydrofuran, The invention can be selected from the group consisting of alkylene, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, dichloromethane, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethylene, 1,1,2-trichloroethylene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, tert-butanol, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, 3-ethoxyethyl propionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether, but is not limited thereto.

本说明书的一实施方式中,以上述感光性树脂组合物的总重量为基准,由上述化学式1表示的化合物的含量为5重量%至60重量%,上述粘合剂树脂的含量为1重量%至60重量%,上述光聚合引发剂的含量为0.1重量%至20重量%,上述多官能性单体的含量为0.1重量%至50重量%,上述溶剂的含量为10重量%至80重量%。In one embodiment of the present specification, based on the total weight of the photosensitive resin composition, the content of the compound represented by the chemical formula 1 is 5 wt % to 60 wt %, the content of the binder resin is 1 wt % to 60 wt %, the content of the photopolymerization initiator is 0.1 wt % to 20 wt %, the content of the multifunctional monomer is 0.1 wt % to 50 wt %, and the content of the solvent is 10 wt % to 80 wt %.

根据本说明书的一实施方式,以上述感光性树脂组合物中的固体成分的总重量为基准,由上述化学式1表示的化合物的含量为5重量%至60重量%,上述粘合剂树脂的含量为1重量%至60重量%,上述光聚合引发剂的含量为0.1重量%至20重量%,上述多官能性单体的含量为0.1重量%至50重量%。According to one embodiment of the present specification, based on the total weight of the solid components in the photosensitive resin composition, the content of the compound represented by the chemical formula 1 is 5 wt % to 60 wt %, the content of the binder resin is 1 wt % to 60 wt %, the content of the photopolymerization initiator is 0.1 wt % to 20 wt %, and the content of the multifunctional monomer is 0.1 wt % to 50 wt %.

具体而言,上述感光性树脂组合物中,以上述感光性树脂组合物中的固体成分的总重量为基准,由上述化学式1表示的化合物的含量为5重量%至50重量%,上述粘合剂树脂的含量为1重量%至50重量%,上述光聚合引发剂的含量为0.1重量%至10重量%,上述多官能性单体的含量为0.1重量%至45重量%。Specifically, in the photosensitive resin composition, based on the total weight of the solid components in the photosensitive resin composition, the content of the compound represented by the chemical formula 1 is 5 wt % to 50 wt %, the content of the binder resin is 1 wt % to 50 wt %, the content of the photopolymerization initiator is 0.1 wt % to 10 wt %, and the content of the multifunctional monomer is 0.1 wt % to 45 wt %.

上述固体成分的总重量是指在树脂组合物中除了溶剂以外的成分的总重量之和。以固体成分和各个成分的固体成分为基准的重量%的基准可以用液相色谱或气相色谱等该领域中使用的一般分析手段进行测定。The total weight of the solid content is the total weight of the components in the resin composition excluding the solvent. The weight % based on the solid content and the solid content of each component can be measured by a general analytical method used in the field such as liquid chromatography or gas chromatography.

根据本说明书的一实施方式,上述感光性树脂组合物可以进一步包含添加剂。According to one embodiment of the present specification, the photosensitive resin composition may further include an additive.

本说明书的一实施方式中,以上述感光性树脂组合物的总重量为基准,可以以0.1重量%至20重量%进一步包含添加剂。In one embodiment of the present specification, the photosensitive resin composition may further contain additives in an amount of 0.1 wt % to 20 wt % based on the total weight of the photosensitive resin composition.

根据本说明书的另一实施方式,以上述感光性树脂组合物中的固体成分的总重量为基准,上述添加剂的含量为0.1重量%至20重量%。According to another embodiment of the present specification, the content of the additive is 0.1 wt % to 20 wt % based on the total weight of the solid content in the photosensitive resin composition.

具体而言,以上述感光性树脂组合物中的固体成分的总重量为基准,上述添加剂的含量为0.1重量%至10重量%。Specifically, the content of the additive is 0.1 wt % to 10 wt % based on the total weight of the solid content in the photosensitive resin composition.

根据本说明书的一实施方式,上述感光性树脂组合物还包含选自光交联敏化剂、固化促进剂、抗氧化剂、密合促进剂、表面活性剂、热聚合抑制剂、紫外线吸收剂、分散剂和流平剂中的1种或2种以上的添加剂。According to one embodiment of the present specification, the photosensitive resin composition further includes one or more additives selected from a photocrosslinking sensitizer, a curing accelerator, an antioxidant, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant, and a leveling agent.

根据本说明书的一实施方式,以上述感光性树脂组合物中的固体成分的总重量为基准,上述添加剂的含量为0.1重量%至20重量%。According to one embodiment of the present specification, the content of the additive is 0.1 wt % to 20 wt % based on the total weight of the solid content in the photosensitive resin composition.

根据本说明书的一实施方式,上述感光性树脂组合物还包含选自光交联敏化剂、固化促进剂、密合促进剂、表面活性剂、热聚合抑制剂、紫外线吸收剂、分散剂和流平剂中的1种或2种以上的添加剂。According to one embodiment of the present specification, the photosensitive resin composition further includes one or more additives selected from a photocrosslinking sensitizer, a curing accelerator, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant, and a leveling agent.

根据本说明书的一实施方式,以上述感光性树脂组合物中的固体成分的总重量为基准,上述添加剂的含量为0.1重量%至20重量%。According to one embodiment of the present specification, the content of the additive is 0.1 wt % to 20 wt % based on the total weight of the solid content in the photosensitive resin composition.

上述光交联敏化剂可以使用选自二苯甲酮、4,4-双(二甲基氨基)二苯甲酮、4,4-双(二乙基氨基)二苯甲酮、2,4,6-三甲基氨基二苯甲酮、邻苯甲酰基苯甲酸甲酯、3,3-二甲基-4-甲氧基二苯甲酮、3,3,4,4-四(叔丁基过氧化羰基)二苯甲酮等二苯甲酮系化合物;9-芴酮、2-氯-9-芴酮、2-甲基-9-芴酮等芴酮系化合物;噻吨酮、2,4-二乙基噻吨酮、2-氯噻吨酮、1-氯-4-丙氧基噻吨酮、异丙基噻吨酮、二异丙基噻吨酮等噻吨酮系化合物;呫吨酮、2-甲基呫吨酮等呫吨酮系化合物;蒽醌、2-甲基蒽醌、2-乙基蒽醌、叔丁基蒽醌、2,6-二氯-9,10-蒽醌等蒽醌系化合物;9-苯基吖啶、1,7-双(9-吖啶基)庚烷、1,5-双(9-吖啶基戊烷)、1,3-双(9-吖啶基)丙烷等吖啶系化合物;苯偶酰、1,7,7-三甲基-二环[2,2,1]庚烷-2,3-二酮、9,10-菲醌等二羰基化合物;2,4,6-三甲基苯甲酰基二苯基氧化膦、双(2,6-二甲氧基苯甲酰基)-2,4,4-三甲基戊基氧化膦等氧化膦系化合物;4-(二甲基氨基)苯甲酸甲酯、4-(二甲基氨基)苯甲酸乙酯、2-正丁氧基乙基-4-(二甲基氨基)苯甲酸酯等苯甲酸酯系化合物;2,5-双(4-二乙基氨基亚苄基)环戊酮、2,6-双(4-二乙基氨基亚苄基)环己酮、2,6-双(4-二乙基氨基亚苄基)-4-甲基-环戊酮等氨基增效剂;3,3-羰基乙烯基-7-(二乙基氨基)香豆素、3-(2-苯并噻唑基)-7-(二乙基氨基)香豆素、3-苯甲酰基-7-(二乙基氨基)香豆素、3-苯甲酰基-7-甲氧基-香豆素、10,10-羰基双[1,1,7,7-四甲基-2,3,6,7-四氢-1H,5H,11H-C1]-苯并吡喃并[6,7,8-ij]-喹嗪-11-酮等香豆素系化合物;4-二乙基氨基查耳酮、4-叠氮亚苄基苯乙酮等查耳酮化合物;以及3-甲基-b-萘并噻唑啉中的1种以上。The photocrosslinking sensitizer may be selected from benzophenone, 4,4-bis(dimethylamino)benzophenone, 4,4-bis(diethylamino)benzophenone, 2,4,6-trimethylaminobenzophenone, methyl o-benzoylbenzoate, 3,3-dimethyl-4-methoxybenzophenone, 3,3,4,4-tetra(tert-butylperoxycarbonyl)benzophenone and the like benzophenone compounds; 9-fluorenone, 2-chloro-9-fluorenone, 2-methyl-9-fluorenone and the like fluorenone compounds; thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propoxythioxanthone, isopropyl Thioxanthone compounds such as thioxanthone and diisopropylthioxanthone; xanthone compounds such as xanthone and 2-methylxanthone; anthraquinone compounds such as anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, tert-butylanthraquinone, 2,6-dichloro-9,10-anthraquinone; acridine compounds such as 9-phenylacridine, 1,7-bis(9-acridinyl)heptane, 1,5-bis(9-acridinylpentane), 1,3-bis(9-acridinyl)propane; dicarbonyl compounds such as benzil, 1,7,7-trimethyl-bicyclo[2,2,1]heptane-2,3-dione, 9,10-phenanthrenequinone; 2,4,6-trimethyl Phosphine oxide compounds such as benzoyldiphenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide; benzoate compounds such as methyl 4-(dimethylamino)benzoate, ethyl 4-(dimethylamino)benzoate, 2-n-butoxyethyl-4-(dimethylamino)benzoate; amino synergists such as 2,5-bis(4-diethylaminobenzylidene)cyclopentanone, 2,6-bis(4-diethylaminobenzylidene)cyclohexanone, 2,6-bis(4-diethylaminobenzylidene)-4-methyl-cyclopentanone; 3,3-carbonylvinyl-7-( Coumarin compounds such as 1,2-diethylamino) coumarin, 3-(2-benzothiazolyl)-7-(diethylamino) coumarin, 3-benzoyl-7-(diethylamino) coumarin, 3-benzoyl-7-methoxy-coumarin, 10,10-carbonylbis[1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-C1]-benzopyrano[6,7,8-ij]-quinolizin-11-one; chalcone compounds such as 4-diethylaminochalcone and 4-azidobenzylideneacetophenone; and 3-methyl-b-naphthothiazoline.

上述固化促进剂用于固化和提高机械强度,具体而言,可以使用选自2-巯基苯并咪唑、2-巯基苯并噻唑、2-巯基苯并唑、2,5-二巯基-1,3,4-噻二唑、2-巯基-4,6-二甲基氨基吡啶、季戊四醇-四(3-巯基丙酸酯)、季戊四醇-三(3-巯基丙酸酯)、季戊四醇-四(2-巯基乙酸酯)、季戊四醇-三(2-巯基乙酸酯)、三羟甲基丙烷-三(2-巯基乙酸酯)、以及三羟甲基丙烷-三(3-巯基丙酸酯)中的1种以上。The curing accelerator is used for curing and improving mechanical strength. Specifically, 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzothiazole, One or more of oxazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis(3-mercaptopropionate), pentaerythritol-tris(3-mercaptopropionate), pentaerythritol-tetrakis(2-mercaptoacetate), pentaerythritol-tris(2-mercaptoacetate), trimethylolpropane-tris(2-mercaptoacetate), and trimethylolpropane-tris(3-mercaptopropionate).

作为本说明书中使用的密合促进剂,可以使用选自甲基丙烯酰氧基丙基三甲氧基硅烷、甲基丙烯酰氧基丙基二甲氧基硅烷、甲基丙烯酰氧基丙基三乙氧基硅烷、甲基丙烯酰氧基丙基二甲氧基硅烷等甲基丙烯酰基硅烷偶联剂中的1种以上,作为烷基三甲氧基硅烷,可以使用选自辛基三甲氧基硅烷、十二烷基三甲氧基硅烷、十八烷基三甲氧基硅烷等中的1种以上。As the adhesion promoter used in this specification, one or more methacrylsilane coupling agents selected from methacryloxypropyltrimethoxysilane, methacryloxypropyldimethoxysilane, methacryloxypropyltriethoxysilane, methacryloxypropyldimethoxysilane, etc. can be used, and as the alkyltrimethoxysilane, one or more selected from octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane, etc. can be used.

上述表面活性剂为硅系表面活性剂或氟系表面活性剂,具体而言,硅系表面活性剂可以使用BYK-Chemie公司的BYK-077、BYK-085、BYK-300、BYK-301、BYK-302、BYK-306、BYK-307、BYK-310、BYK-320、BYK-322、BYK-323、BYK-325、BYK-330、BYK-331、BYK-333、BYK-335、BYK-341v344、BYK-345v346、BYK-348、BYK-354、BYK-355、BYK-356、BYK-358、BYK-361、BYK-370、BYK-371、BYK-375、BYK-380、BYK-390等,作为氟系表面活性剂,可以使用DIC(DaiNippon Ink&Chemicals)公司的F-114、F-177、F-410、F-411、F-450、F-493、F-494、F-443、F-444、F-445、F-446、F-470、F-471、F-472SF、F-474、F-475、F-477、F-478、F-479、F-480SF、F-482、F-483、F-484、F-486、F-487、F-172D、MCF-350SF、TF-1025SF、TF-1117SF、TF-1026SF、TF-1128、TF-1127、TF-1129、TF-1126、TF-1130、TF-1116SF、TF-1131、TF1132、TF1027SF、TF-1441、TF-1442等,但不仅限于此。The above-mentioned surfactant is a silicon-based surfactant or a fluorine-based surfactant. Specifically, the silicon-based surfactant can use BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307, BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-332, BYK-333, BYK-334, BYK-335, BYK-336, BYK-337, BYK-338, BYK-339, BYK-340, BYK-341, BYK-342, BYK-343, BYK-344, BYK-345, BYK-346, BYK-347, BYK-348, BYK-349, BYK-350, BYK-351, BYK-352, BYK-353, BYK-354, BYK-355, BYK-356, BYK-357, BYK-358, BYK-359, BYK-360, BYK-361, BYK-362, BYK-363, BYK-364, BYK-365, BYK-366, BYK-367, BYK-368, BYK-369, BYK-369 As fluorine-based surfactants, DIC (Dai Nippon) can be used. Ink & Chemicals) company's F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446, F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-4 79. F-480SF, F-482, F-483, F-484 , F-486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF, TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, etc., but not limited to.

作为上述抗氧化剂,可以为选自受阻酚系(Hindered phenol)抗氧化剂、胺系抗氧化剂、硫系抗氧化剂、以及膦系抗氧化剂中的1种以上,但不仅限于此。The antioxidant may be one or more selected from the group consisting of hindered phenol antioxidants, amine antioxidants, sulfur antioxidants, and phosphine antioxidants, but is not limited thereto.

作为上述抗氧化剂的具体例子,可列举出如磷酸、磷酸三甲酯或磷酸三乙酯等磷酸系热稳定剂;如2,6-二叔丁基对甲酚、十八烷基-3-(4-羟基-3,5-二叔丁基苯基)丙酸酯、四[亚甲基-3-(3,5-二叔丁基-4-羟基苯基)丙酸酯]甲烷、1,3,5-三甲基-2,4,6-三(3,5-二叔丁基-4-羟基苄基)苯、3,5-二叔丁基-4-羟基苄基亚磷酸二乙酯、2,2-硫代双(4-甲基-6-叔丁基苯酚)、2,6-g,t-丁基苯酚4,4'-亚丁基-双(3-甲基-6-叔丁基苯酚)、4,4’-硫代双(3-甲基-6-叔丁基苯酚)或双[3,3-双-(4’-羟基-3’-叔丁基苯基)丁酸]乙二醇酯(Bis[3,3-bis-(4’-hydroxy-3’-tert-butylphenyl)butanoicacid]glycol ester)等受阻酚(Hindered phenol)系主抗氧化剂;如苯基-α-萘胺、苯基-β-萘胺、N,N’-二苯基-对苯二胺或N,N’-二-β-萘基-对苯二胺等胺系辅助抗氧化剂;二月桂基二硫化物、硫代丙酸二月桂酯、硫代丙酸二硬脂醇酯、巯基苯并噻唑或四甲基秋兰姆二硫化物四[亚甲基-3-(月桂基硫代)丙酸酯]甲烷等硫系辅助抗氧化剂;或如亚磷酸三苯酯、亚磷酸三(壬基苯基)酯、亚磷酸三异癸酯、双(2,4-二丁基苯基)季戊四醇二亚磷酸酯(Bis(2,4-ditbutylphenyl)Pentaerythritol Dip hosphite)或(1,1’-联苯)-4,4’-二基二亚膦酸四[2,4-双(1,1-二甲基乙基)苯基]酯((1,1’-Biphenyl)-4,4’-Diylbisphosphonous acid tetrakis[2,4-bis(1,1-dimet hylethyl)phenyl]ester)等亚磷酸酯系辅助抗氧化剂。Specific examples of the antioxidant include phosphoric acid, trimethyl phosphate, triethyl phosphate, and other phosphoric acid-based heat stabilizers; 2,6-di-tert-butyl-p-cresol, octadecyl-3-(4-hydroxy-3,5-di-tert-butylphenyl) propionate, tetrakis[methylene-3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate]methane, 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, 3,5-di-tert-butyl-4-hydroxybenzyl diethyl phosphite, 2, 2-Thiobis(4-methyl-6-tert-butylphenol), 2,6-g,t-butylphenol, 4,4'-butylene-bis(3-methyl-6-tert-butylphenol), 4,4'-thiobis(3-methyl-6-tert-butylphenol) or Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoic acid]glycol ester) and other hindered phenols as primary antioxidants; amine-based auxiliary antioxidants such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, N,N'-diphenyl-p-phenylenediamine or N,N'-di-β-naphthyl-p-phenylenediamine; sulfur-based auxiliary antioxidants such as dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetrakis[methylene-3-(laurylthio)propionate]methane; or triphenyl phosphite, tris(nonylphenyl) phosphite, triisodecyl phosphite, bis(2,4-dibutylphenyl)pentaerythritol diphosphite Hosphite) or (1,1'-biphenyl)-4,4'-diylbisphosphonous acid tetrakis[2,4-bis(1,1-dimethylethyl)phenyl]ester and other phosphite-based auxiliary antioxidants.

作为上述紫外线吸收剂,可以使用2-(3-叔丁基-5-甲基-2-羟基苯基)-5-氯-苯并三唑、烷氧基二苯甲酮等,但并不限定于此,本领域常用的材料均可以使用。As the ultraviolet absorber, 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chloro-benzotriazole, alkoxybenzophenone, etc. can be used, but it is not limited thereto, and materials commonly used in the art can be used.

作为上述热聚合抑制剂,例如可以包含选自对苯甲醚、氢醌、邻苯二酚(pyrocatechol)、叔丁基邻苯二酚(t-butyl catechol)、N-亚硝基苯基羟基胺铵盐、N-亚硝基苯基羟基胺铝盐、对甲氧基苯酚、二叔丁基对甲酚、连苯三酚、苯醌、4,4-硫代双(3-甲基-6-叔丁基苯酚)、2,2-亚甲基双(4-甲基-6-叔丁基苯酚)、2-巯基咪唑、以及吩噻嗪(phenothiazine)中的1种以上,但不仅限于此,可以包含该技术领域通常已知的热聚合抑制剂。The thermal polymerization inhibitor may include, for example, p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxylamine ammonium salt, N-nitrosophenylhydroxylamine aluminum salt, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, benzoquinone, 4,4-thiobis(3-methyl-6-tert-butylphenol), 2,2-methylenebis(4-methyl-6-tert-butylphenol), 2-mercaptoimidazole, and phenothiazine, but is not limited thereto and may include thermal polymerization inhibitors generally known in the technical field.

上述分散剂可以通过以预先对颜料进行表面处理的形态向颜料进行内部添加的方法、或向颜料进行外部添加的方法来使用。作为上述分散剂,可以使用化合物型、非离子性、阴离子性或阳离子性分散剂,可举出氟系、酯系、阳离子系、阴离子系、非离子系、两性表面活性剂等。这些可以各自使用或组合两种以上使用。The above-mentioned dispersant can be used by a method of adding the pigment internally in a form of pre-surface treatment of the pigment, or by a method of adding the pigment externally. As the above-mentioned dispersant, a compound type, nonionic, anionic or cationic dispersant can be used, and fluorine-based, ester-based, cationic, anionic, nonionic, amphoteric surfactants, etc. can be cited. These can be used individually or in combination of two or more.

具体而言,上述分散剂有选自聚亚烷基二醇及其酯、聚氧化烯多元醇、酯烯化氧加成物、醇烯化氧加成物、磺酸酯、磺酸盐、羧酸酯、羧酸盐、烷基酰胺烯化氧加成物、以及烷基胺中的1种以上,但并不限定于此。Specifically, the dispersant may be one or more selected from polyalkylene glycols and esters thereof, polyoxyalkylene polyols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonic acid salts, carboxylates, carboxylates, alkylamide alkylene oxide adducts, and alkylamines, but is not limited thereto.

作为上述流平剂,可以为聚合性或非聚合性。作为聚合性的流平剂的具体例子,可以举出聚乙烯亚胺、聚酰胺-胺、胺与环氧化物的反应生成物,作为非聚合性的流平剂的具体例子,包含非聚合含硫化合物和非聚合含氮化合物,但并不限定于此,该领域常用的流平剂均可使用。The leveling agent may be polymerizable or non-polymerizable. Specific examples of polymerizable leveling agents include polyethyleneimine, polyamide-amine, and reaction products of amines and epoxides. Specific examples of non-polymerizable leveling agents include non-polymerizable sulfur-containing compounds and non-polymerizable nitrogen-containing compounds, but are not limited thereto, and any leveling agent commonly used in the field may be used.

根据本说明书的一实施方式,提供利用上述感光性树脂组合物制造的感光材料。According to one embodiment of the present specification, a photosensitive material produced using the photosensitive resin composition is provided.

更详细而言,将本说明书的感光性树脂组合物通过合适的方法涂布到基材上,并进行固化,从而形成薄膜或图案形态的感光材料。More specifically, the photosensitive resin composition of the present specification is applied onto a substrate by an appropriate method and cured to form a photosensitive material in the form of a thin film or a pattern.

作为上述涂布方法,没有特别限定,可以使用喷涂法、辊涂法、旋涂法等,一般广泛使用旋涂法。此外,在形成涂覆膜后,可以根据情况,在减压下去除部分残留溶剂。The coating method is not particularly limited, and spray coating, roll coating, spin coating, etc. can be used, and spin coating is generally widely used. In addition, after the coating film is formed, a part of the residual solvent can be removed under reduced pressure according to circumstances.

作为用于使根据本说明书的感光性树脂组合物固化的光源,例如有射出波长在250nm至450nm的光的汞蒸气弧(arc)、碳弧、Xe弧等,但并不限定于此。Examples of a light source for curing the photosensitive resin composition according to the present specification include mercury vapor arc, carbon arc, and Xe arc that emit light with a wavelength of 250 nm to 450 nm, but the present invention is not limited thereto.

根据本说明书的感光性树脂组合物可以用于薄膜晶体管液晶显示装置(TFT LCD)滤色器制造用颜料分散型感光材料、薄膜晶体管液晶显示装置(TFT LCD)或有机发光二极管的黑色矩阵形成用感光材料、外涂层形成用感光材料、柱状间隔物感光材料、光固化型涂料、光固化型油墨、光固化型粘接剂、印刷板、印刷线路板用感光材料、等离子体显示面板(PDP)用感光材料等,但其用途没有特别限定。The photosensitive resin composition according to the present specification can be used for pigment dispersion type photosensitive materials for manufacturing color filters of thin film transistor liquid crystal display devices (TFT LCD), photosensitive materials for forming black matrices of thin film transistor liquid crystal display devices (TFT LCD) or organic light emitting diodes, photosensitive materials for forming outer coatings, columnar spacer photosensitive materials, photocurable coatings, photocurable inks, photocurable adhesives, printed boards, photosensitive materials for printed wiring boards, photosensitive materials for plasma display panels (PDP), etc., but its use is not particularly limited.

根据本说明书的一实施方式,提供包含上述感光材料的滤色器。According to one embodiment of the present specification, a color filter including the above-mentioned photosensitive material is provided.

上述滤色器可以利用包含由上述化学式1表示的化合物的感光性树脂组合物来制造。在基板上涂布上述感光性树脂组合物而形成涂覆膜,并且将上述涂覆膜曝光、显影和固化,从而可以形成滤色器。The color filter may be manufactured using a photosensitive resin composition including the compound represented by Chemical Formula 1. The photosensitive resin composition is applied on a substrate to form a coating film, and the coating film is exposed, developed, and cured, thereby forming the color filter.

根据本说明书的一实施方式的感光性树脂组合物的耐热性优异,基于热处理的颜色变化少,因此可以提供即使在制造滤色器时经过固化过程后色彩再现率也高且亮度和对比度高的滤色器。The photosensitive resin composition according to one embodiment of the present specification has excellent heat resistance and little color change due to heat treatment, so that a color filter having high color reproduction rate, high brightness and high contrast can be provided even after a curing process during color filter production.

上述基板可以为玻璃板、硅片以及聚醚砜(Polyethersulfone,PES)、聚碳酸酯(Polycarbonate,PC)等塑料基材的板等,其种类没有特别限定。The substrate may be a glass plate, a silicon wafer, or a plate made of a plastic base material such as polyethersulfone (PES) or polycarbonate (PC), and the type thereof is not particularly limited.

具体而言,可以将根据本说明书的一实施方式的感光性树脂组合物在玻璃(5×5cm2)上进行旋涂(spincoating),在100℃下实施100秒钟前烘处理(prebake)而形成膜。将形成膜的基板和光掩膜(photo mask)之间的间距设为250um,利用曝光机对基板整面照射40mJ/cm2的曝光量。然后,将曝光的基板在显影液(氢氧化钾(KOH),0.05%)中显影60秒钟,可以以230℃进行20分钟的后烘处理(postbake)而制作基板。Specifically, the photosensitive resin composition according to one embodiment of the present specification can be spin coated on glass (5×5 cm 2 ), and pre-baked at 100° C. for 100 seconds to form a film. The gap between the substrate on which the film is formed and the photomask is set to 250 μm, and the entire surface of the substrate is irradiated with an exposure amount of 40 mJ/cm 2 using an exposure machine. Then, the exposed substrate is developed in a developer (potassium hydroxide (KOH), 0.05%) for 60 seconds, and a post-baking treatment can be performed at 230° C. for 20 minutes to produce a substrate.

上述耐热性评价可以根据后述的方法进行测定,将根据上述一实施方式制作的基板利用光谱仪得到380nm至780nm范围的可见光区域的透射率光谱。此外,将前烘处理(prebake)基板进一步在230℃进行20分钟的后烘处理(postbake),在相同的设备和测定范围内得到了透射率光谱。The heat resistance evaluation can be measured according to the method described below, and the substrate prepared according to the above embodiment is used to obtain a transmittance spectrum in the visible light region of 380nm to 780nm using a spectrometer. In addition, the pre-baked substrate is further post-baked at 230°C for 20 minutes, and the transmittance spectrum is obtained in the same equipment and measurement range.

上述光谱仪可以是MCPD-大冢公司的光谱仪,但并不限定于此。The spectrometer may be a spectrometer manufactured by MCPD-Otsuka Corporation, but is not limited thereto.

利用上述得到的透射率光谱和C光源背光,并利用得到的值E(L*,a*,b*)计算颜色变化(以下称为ΔEab)。ΔEab值小说明颜色耐热性优异。具有ΔEab<3的值时,可以用作滤色器用色素,并且可以说是耐热性优异的色料。具体而言,计算ΔEab的式如下所示。The color change (hereinafter referred to as ΔEab) is calculated using the transmittance spectrum obtained above and the C light source backlight, and the obtained value E (L*, a*, b*). A small ΔEab value indicates that the color has excellent heat resistance. When the value has ΔEab<3, it can be used as a color filter pigment, and it can be said to be a colorant with excellent heat resistance. Specifically, the formula for calculating ΔEab is as follows.

[计算式1][Calculation formula 1]

ΔEab(L*,a*,b*)={(ΔL*)2+(Δa*)2+(Δb*)2}1/2 ΔEab(L*, a*, b*)={(ΔL*) 2 +(Δa*) 2 +(Δb*) 2 } 1/2

上述对比度可以根据后述的方法进行测定。将根据上述基板制作方法制作的基板利用对比度测量仪,在2片偏振片之间放置制作的基板,对2片偏振片水平时的亮度和2片偏振片正交时的亮度进行测定,通过下述计算式2计算对比度。The contrast ratio can be measured by the method described below. The substrate produced by the substrate production method is placed between two polarizing plates using a contrast meter, and the brightness when the two polarizing plates are horizontal and when the two polarizing plates are orthogonal is measured, and the contrast ratio is calculated by the following calculation formula 2.

[计算式2][Calculation formula 2]

对比度=2片偏振片水平时的亮度/2片偏振片垂直时的亮度Contrast = Brightness when two polarizing films are horizontal / Brightness when two polarizing films are vertical

上述对比度测量仪可以是CT-1,ZOENTECH公司的测量仪,但并不限定于此。The above-mentioned contrast measurement instrument may be CT-1, a measurement instrument produced by ZOENTECH, but is not limited thereto.

关于根据本说明书的一实施方式的滤色器的荧光强度,可以对上述基板,利用Sinco公司FS-2荧光测量设备,在常温(25℃)下,将激发波长(excitation wavelength)设为545nm,将发射波长(emission wavelength)设为560nm至720nm,从而测定荧光强度。Regarding the fluorescence intensity of the color filter according to one embodiment of the present specification, the fluorescence intensity can be measured by using a Sinco FS-2 fluorescence measuring device for the above-mentioned substrate at room temperature (25° C.) with the excitation wavelength set to 545 nm and the emission wavelength set to 560 nm to 720 nm.

上述滤色器可以包含红色图案、绿色图案、蓝色图案、黑色矩阵。The color filter may include a red pattern, a green pattern, a blue pattern, and a black matrix.

根据另一实施方式,上述滤色器可以进一步包含外涂层。According to another embodiment, the color filter may further include an overcoat layer.

出于提高对比度的目的,可以在滤色器的彩色像素之间配置被称为黑色矩阵的格子状的黑色图案。作为黑色矩阵的材料,可以使用铬。这时,可以利用将铬在玻璃基板整体上进行蒸镀,并且通过蚀刻处理来形成图案的方式。但是,考虑到工序上的高费用、铬的高反射率、由铬废液导致的环境污染,可以使用利用可进行微加工的颜料分散法而得到的的树脂黑色矩阵。For the purpose of improving contrast, a lattice-shaped black pattern called a black matrix can be arranged between the color pixels of the color filter. As the material of the black matrix, chromium can be used. In this case, chromium can be evaporated on the entire glass substrate and the pattern can be formed by etching. However, considering the high cost of the process, the high reflectivity of chromium, and the environmental pollution caused by chromium waste liquid, a resin black matrix obtained by a pigment dispersion method that can be micro-processed can be used.

上述黑色矩阵可以使用黑色颜料或黑色染料作为色料。例如,可以单独使用碳黑,或者将碳黑和着色颜料混合使用,这时由于混合遮光性不足的着色颜料,因此具有即使相对性地增加色料的量,也不会降低膜的强度或对基板的密合性的优点。The black matrix may use black pigment or black dye as colorant. For example, carbon black may be used alone, or carbon black and a coloring pigment may be mixed and used. At this time, due to the insufficient coloring pigment of the mixed light-shielding property, even if the amount of the colorant is relatively increased, the strength of the film or the adhesion to the substrate may not be reduced.

提供包含根据本说明书的滤色器的显示装置。A display device including the color filter according to the present specification is provided.

上述显示装置可以为等离子体显示器(Plasma Display Panel,PDP)、发光二极管(Light Emitting Diode,LED)、有机发光元件(Organic Light Emitting Diode,OLED)、液晶显示装置(Liquid Crystal Display,LCD)、薄膜晶体管液晶显示装置(Thin FilmTransistor-Liquid Crystal Display,LCD-TFT)、以及阴极射线管(Cathode Ray Tube,CRT)中的任一种。The above-mentioned display device can be any one of a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD), a thin film transistor-liquid crystal display (LCD-TFT), and a cathode ray tube (CRT).

实施发明的方式Modes for Carrying Out the Invention

<实施例><Example>

<化合物的合成实施例><Synthesis Examples of Compounds>

合成例1:化合物1的合成Synthesis Example 1: Synthesis of Compound 1

中间体1的合成Synthesis of intermediate 1

在250ml的双颈圆底烧瓶(RBF,Round Bottom Flask)中加入5g(12.34mmol)的A-1、10.31g(74.03mmol)的B-1和80g的N-甲基-2-吡咯烷酮(NMP,N-Methyl-2-pyrrolidone)进行搅拌。升温至150℃并搅拌4小时,将反应溶液冷却至常温后,加入800ml的1M的盐酸(HCl)并搅拌30分钟。5 g (12.34 mmol) of A-1, 10.31 g (74.03 mmol) of B-1 and 80 g of N-methyl-2-pyrrolidone (NMP) were added to a 250 ml double-necked round bottom flask (RBF) and stirred. The mixture was heated to 150°C and stirred for 4 hours. After the reaction solution was cooled to room temperature, 800 ml of 1 M hydrochloric acid (HCl) was added and stirred for 30 minutes.

然后,将得到的析出物在减压下过滤并洗涤,在60℃真空烘箱中干燥12小时,从而得到了7g(11.46mmol)的中间体1。Then, the obtained precipitate was filtered and washed under reduced pressure, and dried in a vacuum oven at 60° C. for 12 hours to obtain 7 g (11.46 mmol) of Intermediate 1.

离子化模式APCI+:m/z=611[M+H],精确质量(Exact Mass):610Ionization mode APCI+: m/z=611[M+H], Exact Mass: 610

化合物1的合成Synthesis of compound 1

在100ml的双颈圆底烧瓶(RBF,Round Bottom Flask)中,将1.5g(2.46mmol)的中间体1、2.958g(9.82mmol)的C-1、1.358g(9.82mmol)的碳酸钾(K2CO3)加入到30g的N-甲基-2-吡咯烷酮(NMP,N-Methyl-2-pyrrolidone)中进行搅拌。升温至100℃并搅拌6小时,将反应溶液冷却至常温后,加入500ml的蒸馏水(去离子水(DI-Water))并搅拌30分钟。将析出物在减压下过滤并水洗,通过柱层析进行分离,在60℃真空烘箱中干燥12小时,从而得到了1.3g(1.358mmol)的化合物1。In a 100 ml two-necked round bottom flask (RBF, Round Bottom Flask), 1.5 g (2.46 mmol) of intermediate 1, 2.958 g (9.82 mmol) of C-1, and 1.358 g (9.82 mmol) of potassium carbonate (K 2 CO 3 ) were added to 30 g of N-methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrolidone) and stirred. The temperature was raised to 100°C and stirred for 6 hours. After the reaction solution was cooled to room temperature, 500 ml of distilled water (deionized water (DI-Water)) was added and stirred for 30 minutes. The precipitate was filtered under reduced pressure and washed with water, separated by column chromatography, and dried in a vacuum oven at 60°C for 12 hours to obtain 1.3 g (1.358 mmol) of compound 1.

离子化模式APCI+:m/z=957[M+H],精确质量(Exact Mass):956Ionization mode APCI+: m/z = 957 [M + H], Exact Mass: 956

合成例2:化合物2的合成Synthesis Example 2: Synthesis of Compound 2

中间体2的合成Synthesis of intermediate 2

在250ml的双颈圆底烧瓶(RBF,Round Bottom Flask)中加入5g(12.34mmol)的A-1、14.90g(74.03mmol)的B-2和80g的N-甲基-2-吡咯烷酮(NMP,N-Methyl-2-pyrrolidone)进行搅拌。升温至150℃并搅拌4小时,将反应溶液冷却至常温后,加入800ml的1M的盐酸(HCl)并搅拌30分钟。5 g (12.34 mmol) of A-1, 14.90 g (74.03 mmol) of B-2 and 80 g of N-methyl-2-pyrrolidone (NMP) were added to a 250 ml double-necked round bottom flask (RBF) and stirred. The mixture was heated to 150°C and stirred for 4 hours. After the reaction solution was cooled to room temperature, 800 ml of 1 M hydrochloric acid (HCl) was added and stirred for 30 minutes.

然后,将析出物在减压下过滤并水洗,在60℃真空烘箱中干燥12小时,从而得到了7.2g(9.80mmol)的中间体2。Then, the precipitate was filtered under reduced pressure, washed with water, and dried in a vacuum oven at 60° C. for 12 hours to obtain 7.2 g (9.80 mmol) of Intermediate 2.

离子化模式APCI+:m/z=735[M+H],精确质量(Exact Mass):734Ionization mode APCI+: m/z=735[M+H], Exact Mass: 734

化合物2的合成Synthesis of compound 2

在100ml的双颈圆底烧瓶(RBF,Round Bottom Flask)中,将1.808g(2.46mmol)的中间体2、2.958g(9.82mmol)的C-1、1.358g(9.82mmol)的碳酸钾(K2CO3)加入到30g的N-甲基-2-吡咯烷酮(NMP,N-Methyl-2-pyrrolidone)中进行搅拌。升温至100℃并搅拌6小时,将反应溶液冷却至常温后,加入500ml的蒸馏水(去离子水(DI-Water))并搅拌30分钟。In a 100 ml two-necked round bottom flask (RBF, Round Bottom Flask), 1.808 g (2.46 mmol) of Intermediate 2, 2.958 g (9.82 mmol) of C-1, and 1.358 g (9.82 mmol) of potassium carbonate ( K2CO3 ) were added to 30 g of N-methyl- 2 -pyrrolidone (NMP, N-Methyl-2-pyrrolidone) and stirred. The temperature was raised to 100°C and stirred for 6 hours. After the reaction solution was cooled to room temperature, 500 ml of distilled water (deionized water (DI-Water)) was added and stirred for 30 minutes.

然后,将得到的析出物在减压下过滤并水洗,通过柱层析进行分离,在60℃真空烘箱中干燥12小时,从而得到了1g(0.925mmol)的化合物2。Then, the obtained precipitate was filtered under reduced pressure, washed with water, separated by column chromatography, and dried in a vacuum oven at 60° C. for 12 hours to obtain 1 g (0.925 mmol) of Compound 2.

离子化模式APCI+:m/z=1081[M+H],精确质量(Exact Mass):1081Ionization mode APCI+: m/z=1081[M+H], Exact Mass: 1081

合成例3:化合物3的合成Synthesis Example 3: Synthesis of Compound 3

中间体3的合成Synthesis of intermediate 3

在250ml的双颈圆底烧瓶(RBF,Round Bottom Flask)中加入5g(12.34mmol)的A-1、10.31g(74.03mmol)的B-3和80g的N-甲基-2-吡咯烷酮(NMP,N-Methyl-2-pyrrolidone)进行搅拌。升温至150℃并搅拌4小时,将反应溶液冷却至常温后,加入800ml的1M的盐酸(HCl)并搅拌30分钟。5 g (12.34 mmol) of A-1, 10.31 g (74.03 mmol) of B-3 and 80 g of N-methyl-2-pyrrolidone (NMP) were added to a 250 ml double-necked round bottom flask (RBF) and stirred. The mixture was heated to 150°C and stirred for 4 hours. After the reaction solution was cooled to room temperature, 800 ml of 1 M hydrochloric acid (HCl) was added and stirred for 30 minutes.

然后,将析出物在减压下过滤并水洗,在60℃真空烘箱中干燥12小时,从而得到了6.8g(11.130mmol)的中间体3。Then, the precipitate was filtered under reduced pressure, washed with water, and dried in a vacuum oven at 60° C. for 12 hours to obtain 6.8 g (11.130 mmol) of Intermediate 3.

离子化模式APCI+:m/z=611[M+H],精确质量(Exact Mass):610Ionization mode APCI+: m/z=611[M+H], Exact Mass: 610

化合物3的合成Synthesis of compound 3

在100ml的双颈圆底烧瓶(RBF,Round Bottom Flask)中,将1.502g(2.46mmol)的中间体3、2.958g(9.82mmol)的C-1、1.358g(9.82mmol)的碳酸钾(K2CO3)加入到30g的N-甲基-2-吡咯烷酮(NMP,N-Methyl-2-pyrrolidone)中进行搅拌。升温至100℃并搅拌6小时,将反应溶液冷却至常温后,加入500ml的蒸馏水(去离子水(DI-Water))并搅拌30分钟。In a 100 ml two-necked round bottom flask (RBF, Round Bottom Flask), 1.502 g (2.46 mmol) of Intermediate 3, 2.958 g (9.82 mmol) of C-1, and 1.358 g (9.82 mmol) of potassium carbonate ( K2CO3 ) were added to 30 g of N-methyl- 2 -pyrrolidone (NMP, N-Methyl-2-pyrrolidone) and stirred. The temperature was raised to 100°C and stirred for 6 hours. After the reaction solution was cooled to room temperature, 500 ml of distilled water (deionized water (DI-Water)) was added and stirred for 30 minutes.

然后,将析出物在减压下过滤并水洗,通过柱层析进行分离,在60℃真空烘箱中干燥12小时,从而得到了1.4g(1.463mmol)的化合物3。Then, the precipitate was filtered under reduced pressure, washed with water, separated by column chromatography, and dried in a vacuum oven at 60° C. for 12 hours to obtain 1.4 g (1.463 mmol) of Compound 3.

离子化模式APCI+:m/z=957[M+H],精确质量(Exact Mass):956Ionization mode APCI+: m/z = 957 [M + H], Exact Mass: 956

合成例4:化合物4的合成Synthesis Example 4: Synthesis of Compound 4

中间体4的合成Synthesis of intermediate 4

在250ml的双颈圆底烧瓶(RBF,Round Bottom Flask)中加入5g(12.34mmol)的A-1、10.31g(74.03mmol)的B-4和80g的N-甲基-2-吡咯烷酮(NMP,N-Methyl-2-pyrrolidone)进行搅拌。升温至150℃并搅拌4小时,将反应溶液冷却至常温后,加入800ml的1M的盐酸(HCl)并搅拌30分钟。5 g (12.34 mmol) of A-1, 10.31 g (74.03 mmol) of B-4 and 80 g of N-methyl-2-pyrrolidone (NMP) were added to a 250 ml double-necked round bottom flask (RBF) and stirred. The mixture was heated to 150°C and stirred for 4 hours. After the reaction solution was cooled to room temperature, 800 ml of 1 M hydrochloric acid (HCl) was added and stirred for 30 minutes.

然后,将析出物在减压下过滤并水洗,在60℃真空烘箱中干燥12小时,从而得到了6.5g(10.64mmol)的中间体4。Then, the precipitate was filtered under reduced pressure, washed with water, and dried in a vacuum oven at 60° C. for 12 hours to obtain 6.5 g (10.64 mmol) of Intermediate 4.

离子化模式APCI+:m/z=611{M+H],精确质量(Exact Mass):610Ionization mode APCI+: m/z=611{M+H], Exact Mass: 610

化合物4的合成Synthesis of compound 4

在100ml的双颈圆底烧瓶(RBF,Round Bottom Flask)中,将1.502g(2.46mmol)的中间体4、2.958g(9.82mmol)的C-1、1.358g(9.82mmol)的碳酸钾(K2CO3)加入到30g的N-甲基-2-吡咯烷酮(NMP,N-Methyl-2-pyrrolidone)中进行搅拌。升温至100℃并搅拌6小时,将反应溶液冷却至常温后,加入500ml的蒸馏水(去离子水(DI-Water))并搅拌30分钟。In a 100 ml two-necked round bottom flask (RBF, Round Bottom Flask), 1.502 g (2.46 mmol) of intermediate 4, 2.958 g (9.82 mmol) of C-1, and 1.358 g (9.82 mmol) of potassium carbonate ( K2CO3 ) were added to 30 g of N-methyl- 2 -pyrrolidone (NMP, N-Methyl-2-pyrrolidone) and stirred. The temperature was raised to 100°C and stirred for 6 hours. After the reaction solution was cooled to room temperature, 500 ml of distilled water (deionized water (DI-Water)) was added and stirred for 30 minutes.

将析出物在减压下过滤并水洗,通过柱层析进行分离,在60℃真空烘箱中干燥12小时,从而得到了1.7g(1.776mmol)的化合物4。The precipitate was filtered under reduced pressure, washed with water, separated by column chromatography, and dried in a vacuum oven at 60° C. for 12 hours to obtain 1.7 g (1.776 mmol) of Compound 4.

离子化模式APCI+:m/z=957[M+H],精确质量(Exact Mass):956Ionization mode APCI+: m/z = 957 [M + H], Exact Mass: 956

合成例5:化合物5的合成Synthesis Example 5: Synthesis of Compound 5

中间体5的合成Synthesis of intermediate 5

在250ml的双颈圆底烧瓶(RBF,Round Bottom Flask)中,加入5g(12.34mmol)的A-1、14.30g(74.03mmol)的B-5和80g的N-甲基-2-吡咯烷酮(NMP,N-Methyl-2-pyrrolidone)进行搅拌。升温至150℃并搅拌4小时,将反应溶液冷却至常温后,加入800ml的1M的盐酸(HCl)并搅拌30分钟。In a 250 ml double-necked round bottom flask (RBF, Round Bottom Flask), 5 g (12.34 mmol) of A-1, 14.30 g (74.03 mmol) of B-5 and 80 g of N-methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrolidone) were added and stirred. The temperature was raised to 150°C and stirred for 4 hours. After the reaction solution was cooled to room temperature, 800 ml of 1M hydrochloric acid (HCl) was added and stirred for 30 minutes.

然后,将析出物在减压下过滤并水洗,在60℃真空烘箱中干燥12小时,从而得到了7.2g(10.02mmol)的中间体5。Then, the precipitate was filtered under reduced pressure, washed with water, and dried in a vacuum oven at 60° C. for 12 hours to obtain 7.2 g (10.02 mmol) of Intermediate 5.

离子化模式APCI+:m/z=719[M+H],精确质量(Exact Mass):718Ionization mode APCI+: m/z=719 [M+H], Exact Mass: 718

化合物5的合成Synthesis of compound 5

在100ml的双颈圆底烧瓶(RBF,Round Bottom Flask)中,将1.768g(2.46mmol)的中间体5、2.958g(9.82mmol)的C-1、1.358g(9.82mmol)的碳酸钾(K2CO3)加入到30g的N-甲基-2-吡咯烷酮(NMP,N-Methyl-2-pyrrolidone)中进行搅拌。升温至100℃并搅拌6小时,将反应溶液冷却至常温后,加入500ml的蒸馏水(去离子水(DI-Water))并搅拌30分钟。In a 100 ml two-necked round bottom flask (RBF, Round Bottom Flask), 1.768 g (2.46 mmol) of intermediate 5, 2.958 g (9.82 mmol) of C-1, and 1.358 g (9.82 mmol) of potassium carbonate ( K2CO3 ) were added to 30 g of N-methyl- 2 -pyrrolidone (NMP, N-Methyl-2-pyrrolidone) and stirred. The temperature was raised to 100°C and stirred for 6 hours. After the reaction solution was cooled to room temperature, 500 ml of distilled water (deionized water (DI-Water)) was added and stirred for 30 minutes.

将析出物在减压下过滤并水洗,通过柱层析进行分离,在60℃真空烘箱中干燥12小时,从而得到了2.1g(1.972mmol)的化合物5。The precipitate was filtered under reduced pressure, washed with water, separated by column chromatography, and dried in a vacuum oven at 60° C. for 12 hours to obtain 2.1 g (1.972 mmol) of Compound 5.

离子化模式APCI+:m/z=1065[M+H],精确质量(Exact Mass):1064Ionization mode APCI+: m/z=1065[M+H], Exact Mass: 1064

合成例6:化合物6的合成Synthesis Example 6: Synthesis of Compound 6

中间体6的合成Synthesis of intermediate 6

在250ml的双颈圆底烧瓶(RBF,Round Bottom Flask)中,加入5g(12.34mmol)的A-1、15.33g(74.03mmol)的B-6和80g的N-甲基-2-吡咯烷酮(NMP,N-Methyl-2-pyrrolidone)进行搅拌。升温至150℃并搅拌4小时,将反应溶液冷却至常温后,加入800ml的1M的盐酸(HCl)并搅拌30分钟。In a 250 ml double-necked round bottom flask (RBF, Round Bottom Flask), 5 g (12.34 mmol) of A-1, 15.33 g (74.03 mmol) of B-6 and 80 g of N-methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrolidone) were added and stirred. The temperature was raised to 150°C and stirred for 4 hours. After the reaction solution was cooled to room temperature, 800 ml of 1M hydrochloric acid (HCl) was added and stirred for 30 minutes.

将析出物在减压下过滤并水洗,在60℃真空烘箱中干燥12小时,从而得到了7.4g(9.91mmol)的中间体6。The precipitate was filtered under reduced pressure, washed with water, and dried in a vacuum oven at 60° C. for 12 hours to obtain 7.4 g (9.91 mmol) of Intermediate 6.

离子化模式APCI+:m/z=747[M+H],精确质量(Exact Mass):746Ionization mode APCI+: m/z=747 [M+H], Exact Mass: 746

化合物6的合成Synthesis of compound 6

在100ml的双颈圆底烧瓶(RBF,Round Bottom Flask)中,将1.837g(2.46mmol)的中间体6、2.958g(9.82mmol)的C-1、1.358g(9.82mmol)的碳酸钾(K2CO3)加入到30g的N-甲基-2-吡咯烷酮(NMP,N-Methyl-2-pyrrolidone)中进行搅拌。升温至100℃并搅拌6小时,将反应溶液冷却至常温后,加入500ml的蒸馏水(去离子水(DI-Water))并搅拌30分钟。In a 100 ml two-necked round bottom flask (RBF, Round Bottom Flask), 1.837 g (2.46 mmol) of intermediate 6, 2.958 g (9.82 mmol) of C-1, and 1.358 g (9.82 mmol) of potassium carbonate ( K2CO3 ) were added to 30 g of N-methyl- 2 -pyrrolidone (NMP, N-Methyl-2-pyrrolidone) and stirred. The temperature was raised to 100°C and stirred for 6 hours. After the reaction solution was cooled to room temperature, 500 ml of distilled water (deionized water (DI-Water)) was added and stirred for 30 minutes.

将析出物在减压下过滤并水洗,通过柱层析进行分离,在60℃真空烘箱中干燥12小时,从而得到了2.5g(2.287mmol)的化合物6。The precipitate was filtered under reduced pressure, washed with water, separated by column chromatography, and dried in a vacuum oven at 60° C. for 12 hours to obtain 2.5 g (2.287 mmol) of Compound 6.

离子化模式APCI+:m/z=1093[M+H],精确质量(Exact Mass):1092Ionization mode APCI+: m/z=1093[M+H], Exact Mass: 1092

合成例7:化合物7的合成Synthesis Example 7: Synthesis of Compound 7

在上述化合物1的制造中,将C-1变更为C-2,除此以外,通过相同的方法得到了化合物7。Compound 7 was obtained by the same method as in the preparation of Compound 1, except that C-1 was changed to C-2.

离子化模式APCI+:m/z=985[M+H],精确质量(Exact Mass):984Ionization mode APCI+: m/z = 985 [M + H], Exact Mass: 984

合成例8:化合物8的合成Synthesis Example 8: Synthesis of Compound 8

在上述化合物2的制造中,将C-1变更为C-2,除此以外,通过相同的方法得到了化合物8。Compound 8 was obtained by the same method as above except that C-1 was changed to C-2 in the preparation of Compound 2.

离子化模式APCI+:m/z=1109[M+H],精确质量(Exact Mass):1108Ionization mode APCI+: m/z=1109 [M+H], Exact Mass: 1108

合成例9:化合物9的合成Synthesis Example 9: Synthesis of Compound 9

在上述化合物3的制造中,将C-1变更为C-2,除此以外,通过相同的方法得到了化合物9。Compound 9 was obtained by the same method as in the preparation of Compound 3, except that C-1 was changed to C-2.

离子化模式APCI+:m/z=985[M+H],精确质量(Exact Mass):984Ionization mode APCI+: m/z = 985 [M + H], Exact Mass: 984

合成例10:化合物10的合成Synthesis Example 10: Synthesis of Compound 10

在上述化合物4的制造中,将C-1变更为C-2,除此以外,通过相同的方法得到了化合物10。Compound 10 was obtained by the same method as in the preparation of Compound 4, except that C-1 was changed to C-2.

离子化模式APCI+:m/z=985[M+H],精确质量(Exact Mass):984Ionization mode APCI+: m/z = 985 [M + H], Exact Mass: 984

合成例11:化合物11的合成Synthesis Example 11: Synthesis of Compound 11

在上述化合物5的制造中,将C-1变更为C-2,除此以外,通过相同的方法得到了化合物11。Compound 11 was obtained by the same method as in the preparation of Compound 5, except that C-1 was changed to C-2.

离子化模式APCI+:m/z=1093[M+H],精确质量(Exact Mass):1092Ionization mode APCI+: m/z=1093[M+H], Exact Mass: 1092

合成例12:化合物12的合成Synthesis Example 12: Synthesis of Compound 12

在上述化合物6的制造中,将C-1变更为C-2,除此以外,通过相同的方法得到了化合物12。Compound 12 was obtained by the same method as in the preparation of Compound 6, except that C-1 was changed to C-2.

离子化模式APCI+:m/z=1121[M+H],精确质量(Exact Mass):1120Ionization mode APCI+: m/z=1121[M+H], Exact Mass: 1120

合成例13至18:化合物13至18的合成Synthesis Examples 13 to 18: Synthesis of Compounds 13 to 18

在化合物1至6的制造中,将C-1变更为C-3,除此以外,通过相同的方法得到了如下述所示的化合物13至18。In the preparation of compounds 1 to 6, compounds 13 to 18 shown below were obtained by the same method except that C-1 was changed to C-3.

化合物13:离子化模式APCI+:m/z=1085[M+H],精确质量(Exact Mass):1084Compound 13: Ionization mode APCI+: m/z=1085 [M+H], Exact Mass: 1084

化合物14:离子化模式APCI+:m/z=1209[M+H],精确质量(Exact Mass):1208Compound 14: Ionization mode APCI+: m/z=1209 [M+H], Exact Mass: 1208

化合物15:离子化模式APCI+:m/z=1085[M+H],精确质量(Exact Mass):1084Compound 15: Ionization mode APCI+: m/z=1085 [M+H], Exact Mass: 1084

化合物16:离子化模式APCI+:m/z=1085[M+H],精确质量(Exact Mass):1084Compound 16: Ionization mode APCI+: m/z=1085 [M+H], Exact Mass: 1084

化合物17:离子化模式APCI+:m/z=1193[M+H],精确质量(Exact Mass):1192Compound 17: Ionization mode APCI+: m/z=1193 [M+H], Exact Mass: 1192

化合物18:离子化模式APCI+:m/z=1221[M+H],精确质量(Exact Mass):1220Compound 18: Ionization mode APCI+: m/z=1221 [M+H], Exact Mass: 1220

比较化合物1.Comparative Compound 1.

在100ml的双颈圆底烧瓶(RBF,Round Bottom Flask)中,将1.414g(2.46mmol)的S1、1.21g(9.82mmol)的溴丙烷(bromopropane)、1.358g(9.82mmol)的碳酸钾(K2CO3)加入到30g的N-甲基-2-吡咯烷酮(NMP,N-Methyl-2-pyrrolidone)中进行搅拌。升温至100℃并搅拌6小时,将反应溶液冷却至常温后,加入500ml的蒸馏水(去离子水(DI-Water))并搅拌30分钟。In a 100 ml two-necked round bottom flask (RBF, Round Bottom Flask), 1.414 g (2.46 mmol) of S1, 1.21 g (9.82 mmol) of bromopropane, and 1.358 g (9.82 mmol) of potassium carbonate ( K2CO3 ) were added to 30 g of N-methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrolidone) and stirred. The temperature was raised to 100°C and stirred for 6 hours. After the reaction solution was cooled to room temperature, 500 ml of distilled water (deionized water (DI-Water)) was added and stirred for 30 minutes.

将析出物在减压下过滤并水洗,通过柱层析进行分离,在60℃真空烘箱中干燥12小时,从而得到了比较化合物1。The precipitate was filtered under reduced pressure, washed with water, separated by column chromatography, and dried in a vacuum oven at 60° C. for 12 hours, thereby obtaining Comparative Compound 1.

离子化模式APCI+:m/z=659[M+H],精确质量(Exact Mass):658Ionization mode APCI+: m/z=659[M+H], Exact Mass: 658

比较化合物2Comparative Compound 2

在100ml的双颈圆底烧瓶(RBF,Round Bottom Flask)中,将1.4234g(2.46mmol)的S2、3.094g(9.82mmol)的C-2、1.358g(9.82mmol)的碳酸钾(K2CO3)加入到30g的N-甲基-2-吡咯烷酮(NMP,N-Methyl-2-pyrrolidone)中进行搅拌。升温至100℃并搅拌6小时,将反应溶液冷却至常温后,加入500ml的蒸馏水(去离子水(DI-Water))并搅拌30分钟。In a 100 ml two-necked round bottom flask (RBF, Round Bottom Flask), 1.4234 g (2.46 mmol) of S2, 3.094 g (9.82 mmol) of C-2, and 1.358 g (9.82 mmol ) of potassium carbonate ( K2CO3 ) were added to 30 g of N-methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrolidone) and stirred. The temperature was raised to 100°C and stirred for 6 hours. After the reaction solution was cooled to room temperature, 500 ml of distilled water (deionized water (DI-Water)) was added and stirred for 30 minutes.

将析出物在减压下过滤并水洗,通过柱层析进行分离,在60℃真空烘箱中干燥12小时,从而得到了比较化合物2。The precipitate was filtered under reduced pressure, washed with water, separated by column chromatography, and dried in a vacuum oven at 60° C. for 12 hours, thereby obtaining Comparative Compound 2.

离子化模式APCI+:m/z=953[M+H],精确质量(Exact Mass):952Ionization mode APCI+: m/z = 953 [M + H], Exact Mass: 952

比较化合物3Comparative Compound 3

在合成例1中,通过与中间体1的合成相同的方法,利用S3和S4代替A-1和B-1,从而合成了比较化合物3。In Synthesis Example 1, Comparative Compound 3 was synthesized by the same method as in the synthesis of Intermediate 1 except that S3 and S4 were used instead of A-1 and B-1.

比较化合物4Comparative Compound 4

在10℃的98%硫酸50g中,加入3g(4.553mmol)的比较化合物1进行溶解。然后,加入0.807g(4.553mmol)的N-羟甲基邻苯二甲酰亚胺(N-hydroxymethylphthalimide),升温至45℃并搅拌2小时。将反应溶液添加到500g的水中析出结晶,将析出物在减压下过滤而得到了比较化合物4。3 g (4.553 mmol) of comparative compound 1 was added to 50 g of 98% sulfuric acid at 10°C and dissolved. Then, 0.807 g (4.553 mmol) of N-hydroxymethylphthalimide was added, the temperature was raised to 45°C and stirred for 2 hours. The reaction solution was added to 500 g of water to precipitate crystals, and the precipitate was filtered under reduced pressure to obtain comparative compound 4.

实施例1Example 1

将5.554g的化合物1、10.376g的作为粘合剂树脂的甲基丙烯酸苄酯与甲基丙烯酸的共聚物(摩尔比70:30,酸值为113KOH mg/g,用凝胶渗透色谱(GPC)测定的重均分子量20000g/mol,分子量分布(PDI)2.0g,固体成分(S.C)25%,包含溶剂聚丙二醇单甲醚乙酸酯(PGMEA))、2.018g的作为光聚合引发剂的I-369(BASF公司)、12.443g的作为多官能性单体的DPHA(日本化药)、68.593g的溶剂PGMEA(聚丙二醇单甲醚乙酸酯)、以及1.016g的作为添加剂的表面活性剂DIC公司的F-475进行混合,从而制造了感光性树脂组合物1。5.554 g of compound 1, 10.376 g of a copolymer of benzyl methacrylate and methacrylic acid as a binder resin (molar ratio 70:30, acid value 113 KOH mg/g, weight average molecular weight 20000 g/mol measured by gel permeation chromatography (GPC), molecular weight distribution (PDI) 2.0 g, solid content (S.C) 25%, containing solvent polypropylene glycol monomethyl ether acetate (PGMEA)), 2.018 g of I-369 (BASF) as a photopolymerization initiator, 12.443 g of DPHA (Nippon Kayaku) as a multifunctional monomer, 68.593 g of solvent PGMEA (polypropylene glycol monomethyl ether acetate), and 1.016 g of surfactant F-475 of DIC Corporation as an additive were mixed to produce a photosensitive resin composition 1.

实施例2至18Examples 2 to 18

在实施例1中,将化合物1变更为化合物2至18,除此以外,利用相同的组成分别制造了感光性树脂组合物2至18。In Example 1, except that Compound 1 was changed to Compounds 2 to 18, photosensitive resin compositions 2 to 18 were respectively produced with the same composition.

比较例1Comparative Example 1

将5.554g的比较化合物1、10.376g的作为粘合剂树脂的甲基丙烯酸苄酯和甲基丙烯酸的共聚物(摩尔比70:30,酸值为113KOH mg/g,用凝胶渗透色谱(GPC)测定的重均分子量20000g/mol,分子量分布(PDI)2.0g,固体成分(S.C)25%,包含溶剂聚丙二醇单甲醚乙酸酯(PGMEA))、2.018g的作为光聚合引发剂的I-369(BASF公司)、12.443g的作为多官能性单体的DPHA(日本化药)、68.593g的溶剂PGMEA(聚丙二醇单甲醚乙酸酯)、以及1.016g的作为添加剂的表面活性剂DIC公司的F-475进行混合,从而制造了比较例1的感光性树脂组合物。5.554 g of comparative compound 1, 10.376 g of a copolymer of benzyl methacrylate and methacrylic acid as a binder resin (molar ratio 70:30, acid value 113 KOH mg/g, weight average molecular weight 20000 g/mol measured by gel permeation chromatography (GPC), molecular weight distribution (PDI) 2.0 g, solid content (S.C) 25%, containing solvent polypropylene glycol monomethyl ether acetate (PGMEA)), 2.018 g of I-369 (BASF) as a photopolymerization initiator, 12.443 g of DPHA (Nippon Kayaku) as a multifunctional monomer, 68.593 g of solvent PGMEA (polypropylene glycol monomethyl ether acetate), and 1.016 g of surfactant F-475 of DIC Corporation as an additive were mixed to prepare a photosensitive resin composition of Comparative Example 1.

比较例2至4Comparative Examples 2 to 4

在上述比较例1中,将比较化合物1分别变更为比较化合物2至4,除此以外,通过相同的组成制造了比较例2至4的感光性树脂组合物。In the above-mentioned Comparative Example 1, except having changed the Comparative Compound 1 into the Comparative Compounds 2 to 4, respectively, the photosensitive resin compositions of Comparative Examples 2 to 4 were produced with the same composition.

<实验例><Experimental example>

基板制作Substrate production

将根据上述实施例1至18、比较例1至4的感光性树脂组合物分别用于基板制作。具体而言,将根据上述实施例1至18、比较例1至4的感光性树脂组合物在玻璃(5×5cm2)上进行旋涂(spincoating),在100℃实施100秒钟前烘处理(prebake)而形成了膜。The photosensitive resin compositions of Examples 1 to 18 and Comparative Examples 1 to 4 were used to prepare substrates. Specifically, the photosensitive resin compositions of Examples 1 to 18 and Comparative Examples 1 to 4 were spin coated on glass (5×5 cm 2 ) and pre-baked at 100° C. for 100 seconds to form films.

将形成膜的基板与光掩膜(photo mask)之间的间距设为250um,利用曝光机对基板整面照射40mJ/cm2的曝光量。然后,将曝光的基板在显影液(氢氧化钾(KOH),0.05%)中显影60秒钟,以230℃进行20分钟的后烘处理(post bake)而制作基板。The gap between the substrate on which the film is to be formed and the photomask is set to 250 μm, and the entire surface of the substrate is irradiated with an exposure dose of 40 mJ/cm 2 using an exposure machine. Then, the exposed substrate is developed in a developer (potassium hydroxide (KOH), 0.05%) for 60 seconds, and a post-baking treatment is performed at 230° C. for 20 minutes to prepare the substrate.

耐热性评价Heat resistance evaluation

将根据上述基板制作方法制作的基板利用光谱仪(MCPD-大冢公司)得到了380nm至780nm范围的可见光区域的透射率光谱。此外,将前烘处理(prebake)基板进一步在230℃进行20分钟后烘处理(post bake),在相同的设备和测定范围内得到了透射率光谱。The substrate prepared according to the above-mentioned substrate preparation method was used to obtain a transmittance spectrum in the visible light region ranging from 380nm to 780nm using a spectrometer (MCPD-Otsuka Co., Ltd.). In addition, the pre-baked substrate was further post-baked at 230°C for 20 minutes, and the transmittance spectrum was obtained using the same equipment and measurement range.

利用得到的透射率光谱和C光源背光,并利用得到的值E(L*,a*,b*)计算颜色变化(以下称为△Eab),示于下述表1。The color change (hereinafter referred to as ΔEab) was calculated using the obtained transmittance spectrum and C light source backlight and the obtained values E (L*, a*, b*), and is shown in Table 1 below.

ΔEab值小说明颜色耐热性优异。A small ΔEab value indicates excellent heat resistance of the color.

当具有ΔEab<3的值时,可以作为滤色器用色素使用,可以说是耐热性优异的色料。具体而言,计算ΔEab的式如下所示。When the value of ΔEab<3 is achieved, the colorant can be used as a color filter dye, and can be said to be a colorant with excellent heat resistance. Specifically, the formula for calculating ΔEab is as follows.

[计算式1][Calculation formula 1]

ΔEab(L*,a*,b*)={(ΔL*)2+(Δa*)2+(Δb*)2}1/2 ΔEab(L*, a*, b*)={(ΔL*) 2 +(Δa*) 2 +(Δb*) 2 } 1/2

[表1][Table 1]

ΔEab(后烘处理-前烘处理)ΔEab (post-baking treatment - pre-baking treatment) 实施例1Example 1 1.281.28 实施例2Example 2 1.271.27 实施例3Example 3 0.850.85 实施例4Example 4 1.361.36 实施例5Example 5 1.751.75 实施例6Example 6 0.940.94 实施例7Example 7 1.451.45 实施例8Example 8 1.391.39 实施例9Embodiment 9 1.121.12 实施例10Example 10 1.471.47 实施例11Embodiment 11 1.681.68 实施例12Example 12 1.271.27 实施例13Example 13 0.970.97 实施例14Embodiment 14 1.541.54 实施例15Embodiment 15 1.981.98 实施例16Example 16 1.761.76 实施例17Embodiment 17 1.641.64 实施例18Embodiment 18 1.441.44

参考上述表1,利用本发明的实施例1至18的感光性树脂组合物形成的彩色图案基板,后烘处理和后烘处理后透射光谱之差(ΔEab)小于3,可以确认颜色稳定性高且耐热性优异。Referring to Table 1, the color pattern substrates formed using the photosensitive resin compositions of Examples 1 to 18 of the present invention have a difference (ΔEab) in the transmission spectrum before and after the post-bake treatment of less than 3, which confirms high color stability and excellent heat resistance.

对比度测定Contrast measurement

将根据上述基板制作方法制作的基板利用对比度测量仪(CT-1,ZOENTECH公司),在2片偏振片之间放入制作的基板,对2片偏振片水平时的亮度和2片偏振片正交时的亮度进行测定,用下述计算式2计算出对比度。The substrate produced according to the above-mentioned substrate production method is placed between two polarizing plates using a contrast meter (CT-1, ZOENTECH). The brightness when the two polarizing plates are horizontal and when the two polarizing plates are orthogonal are measured, and the contrast is calculated using the following calculation formula 2.

[计算式2][Calculation formula 2]

对比度=2片偏振片水平时的亮度/2片偏振片垂直时的亮度Contrast = Brightness when two polarizing films are horizontal / Brightness when two polarizing films are vertical

将根据上述计算式2计算的对比度用下述计算式3计算出对比度改善率,记载于下述表2。The contrast calculated by the above-mentioned calculation formula 2 was used to calculate the contrast improvement rate using the following calculation formula 3, and the result is recorded in the following Table 2.

[计算式3][Calculation formula 3]

对比度改善率=(实施例的对比度-比较例1、2或4的对比度)/比较例1、2或4的对比度*100Contrast improvement rate = (contrast of the embodiment - contrast of comparative example 1, 2 or 4) / contrast of comparative example 1, 2 or 4 * 100

[表2][Table 2]

参考上述表2可以确认,与上述比较例1相比,上述实施例1至18的对比度改善了220.47%至532.38%。此外,可以确认,与上述比较例2相比,上述实施例1至18的对比度改善了136.48%至329.57%。此外,可以确认,与上述比较例4相比,上述实施例1至18的对比度改善了197.83%至510.43%。With reference to Table 2, it can be confirmed that the contrast ratios of Examples 1 to 18 are improved by 220.47% to 532.38% compared to Comparative Example 1. It can also be confirmed that the contrast ratios of Examples 1 to 18 are improved by 136.48% to 329.57% compared to Comparative Example 2. It can also be confirmed that the contrast ratios of Examples 1 to 18 are improved by 197.83% to 510.43% compared to Comparative Example 4.

荧光强度测定Fluorescence intensity measurement

对根据上述基板制作方法制作的基板,利用Sinco公司FS-2荧光测量设备,在常温(25℃)下,将激发波长(excitation wavelength)设为545nm,将发射波长(emissionwavelength)设为560nm至720nm而测定荧光强度,并示于图1。The fluorescence intensity of the substrate produced according to the above-mentioned substrate production method was measured using a Sinco FS-2 fluorescence measuring device at room temperature (25° C.) with an excitation wavelength of 545 nm and an emission wavelength of 560 nm to 720 nm. The fluorescence intensity is shown in FIG. 1 .

根据图1,可以确认,根据本说明书的一实施方式的实施例6、7和12的荧光强度低于比较例1和2,在不添加追加的染料的情况下,也可以得到优异的对比度。According to FIG. 1 , it can be confirmed that the fluorescence intensity of Examples 6, 7, and 12 according to one embodiment of the present specification is lower than that of Comparative Examples 1 and 2, and that excellent contrast can be obtained without adding an additional dye.

透射率评价Transmittance evaluation

将根据上述基板制作方法制作的基板,利用光谱仪(MCPD-大冢公司),以230℃进行20分钟后烘处理(postbake),从而得到了380nm至780nm范围的可见光区域的透射率光谱。The substrate produced by the above-mentioned substrate production method was post-baked at 230° C. for 20 minutes using a spectrometer (MCPD, Otsuka Corporation), thereby obtaining a transmittance spectrum in the visible light region ranging from 380 nm to 780 nm.

特别是在蓝色滤色器的情况下,在视觉x、视觉y、视觉z中,在380nm~480nm下最大透射率高的情况下,可以显示出更优异的亮度。In particular, in the case of a blue color filter, when the maximum transmittance is high at 380 nm to 480 nm in visual x, visual y, and visual z, more excellent brightness can be exhibited.

图2表示视觉x、视觉y、视觉z。Figure 2 shows visual x, visual y, and visual z.

[表3][Table 3]

透射率%(在380nm~480nm下的最大透射率%)Transmittance % (maximum transmittance % at 380nm ~ 480nm) 实施例1Example 1 95.75695.756 实施例7Example 7 92.90692.906 实施例13Example 13 95.72195.721 比较例3Comparative Example 3 88.52888.528

参考上述表3可知,与上述比较例3相比,上述实施例1和7、13的在380nm~480nm下的最大透射率高。With reference to Table 3, it can be seen that the maximum transmittances of Examples 1, 7, and 13 at 380 nm to 480 nm are higher than that of Comparative Example 3.

根据图3可以确认,根据本说明书的一实施方式的实施例1、7和13的在380nm~480nm下的透射率大于比较例3,在蓝色滤色器中能够显示出更优异的亮度。3 , it can be confirmed that Examples 1, 7, and 13 according to one embodiment of the present specification have a transmittance at 380 nm to 480 nm greater than that of Comparative Example 3, and can exhibit more excellent brightness in the blue color filter.

Claims (12)

1.一种由下述化学式1表示的化合物:1. A compound represented by the following chemical formula 1: 化学式1Chemical formula 1 在所述化学式1中,In the chemical formula 1, L1和L2彼此相同或不同,各自独立地为碳原子数1至20的直链或支链的亚烷基,L1 and L2 are the same or different from each other, and are each independently a linear or branched alkylene group having 1 to 20 carbon atoms, R1和R2彼此相同或不同,各自独立地为含有氮原子的二酐基团,R1 and R2 are the same or different from each other and are each independently a dianhydride group containing a nitrogen atom, R3和R4彼此相同或不同,各自独立地为经卤素基团取代或未取代的碳原子数1至20的烷基、或者经卤素基团取代或未取代的碳原子数6至20的芳基,R3 and R4 are the same as or different from each other, and are each independently an alkyl group having 1 to 20 carbon atoms, which may be substituted by a halogen group or an aryl group having 6 to 20 carbon atoms, which may be substituted by a halogen group or an aryl group having 6 to 20 carbon atoms, R5至R6彼此相同或不同,各自独立地选自氢、氘、卤素基团、-SO2NHY、或者经卤素基团取代或未取代的碳原子数1至20的烷基,R5 to R6 are the same as or different from each other, and are independently selected from hydrogen, deuterium, a halogen group, -SO 2 NHY, or an alkyl group having 1 to 20 carbon atoms which may be substituted with a halogen group. R7至R12彼此相同或不同,各自独立地选自氢或氘,R7 to R12 are the same as or different from each other and are each independently selected from hydrogen or deuterium, R13至R17彼此相同或不同,各自独立地为氢、氘、卤素基团、-SO3 -、-SO3M、-或-SO2NHY,R13 to R17 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, -SO 3 - , -SO 3 M, - or -SO 2 NHY, 所述M选自Na+、K+、Rb+、Cs+、Fr+、以及包含铵结构的部分,The M is selected from Na + , K + , Rb + , Cs + , Fr + , and a portion containing an ammonium structure, 所述Y为碳原子数1至20的烷基,Y is an alkyl group having 1 to 20 carbon atoms, 所述R13至R17中的至少一个为-SO3 -At least one of R13 to R17 is -SO 3 - , X为阴离子性基团,X is an anionic group, a为0,a is 0, r5和r6为0至4的整数,r5为2以上时R5彼此相同或不同,r6为2以上时R6彼此相同或不同,r5 and r6 are integers from 0 to 4, when r5 is 2 or more, R5 are the same or different from each other, and when r6 is 2 or more, R6 are the same or different from each other, 其中,所述含有氮原子的二酐基团由下述取代基中的任一个表示:Wherein, the dianhydride group containing a nitrogen atom is represented by any one of the following substituents: 在所述取代基中,表示与所述化学式1中的L1或L2连接的部位,In the substituent, represents a site connected to L1 or L2 in the chemical formula 1, X3至X5和Y4彼此相同或不同,各自独立地为氢、氘、-SO3M、或-SO2NHY,所述M和Y与所述化学式1中的定义相同,x3为0至4的整数,x4、x5和y4为0至6的整数。X3 to X5 and Y4 are the same as or different from each other and are independently hydrogen, deuterium, —SO 3 M, or —SO 2 NHY; M and Y are the same as defined in Chemical Formula 1; x3 is an integer of 0-4; and x4, x5, and y4 are integers of 0-6. 2.根据权利要求1所述的化合物,其中,2. The compound according to claim 1, wherein 所述包含铵结构的部分包含由下述化学式A表示或由下述化学式B表示的单元:The ammonium structure-containing portion includes a unit represented by the following chemical formula A or a unit represented by the following chemical formula B: 化学式AChemical formula A 化学式BChemical formula B 在所述化学式A中,In the chemical formula A, Ra至Rd彼此相同或不同,各自独立地为氢、碳原子数1至20的烷基、碳原子数1至20的烯基、碳原子数6至20的芳基、碳原子数6至20的芳烷基、-L1-NHCO-R、或-L2-OCO-R,Ra to Rd are the same as or different from each other, and are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 6 to 20 carbon atoms, -L 1 -NHCO-R, or -L 2 -OCO-R, 所述R为氢、碳原子数1至20的烷基、碳原子数6至20的芳基、或者碳原子数6至20的芳烷基,R is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 6 to 20 carbon atoms, 所述L1和L2为碳原子数1至20的亚烷基,The L1 and L2 are alkylene groups having 1 to 20 carbon atoms, 在所述化学式B中,In the chemical formula B, Rb至Rd彼此相同或不同,各自独立地为氢、碳原子数1至20的烷基、碳原子数1至20的烯基、碳原子数6至20的芳基、或者碳原子数6至20的芳烷基,Rb to Rd are the same as or different from each other, and are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 6 to 20 carbon atoms, Z为碳原子数1至20的亚烷基、碳原子数6至20的亚芳基、-L3-NHCO-、或-L4-OCO-,Z is an alkylene group having 1 to 20 carbon atoms, an arylene group having 6 to 20 carbon atoms, -L 3 -NHCO-, or -L 4 -OCO-, 所述L3和L4为碳原子数1至20的亚烷基,The L3 and L4 are alkylene groups having 1 to 20 carbon atoms, Re至Rg彼此相同或不同,各自独立地为氢、或者碳原子数1至20的烷基。Re to Rg are the same as or different from each other, and are each independently hydrogen or an alkyl group having 1 to 20 carbon atoms. 3.根据权利要求1所述的化合物,其中,所述化学式1由下述化学式2表示:3. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 2: 化学式2Chemical formula 2 在所述化学式2中,In the chemical formula 2, L1、L2、R1至R17、X、a、r5和r6与所述化学式1中的定义相同。L1, L2, R1 to R17, X, a, r5 and r6 are the same as defined in Chemical Formula 1. 4.根据权利要求1所述的化合物,其中,所述化学式1由下述化学式3表示:4. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 3: 化学式3Chemical formula 3 在所述化学式3中,In the chemical formula 3, L1、L2、R1至R17、X、a、r5和r6与所述化学式1中的定义相同。L1, L2, R1 to R17, X, a, r5 and r6 are the same as defined in Chemical Formula 1. 5.根据权利要求1所述的化合物,其中,所述化学式1由下述化学式4表示:5. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 4: 化学式4Chemical formula 4 在所述化学式4中,In the chemical formula 4, L1、L2、R1至R17、X、a、r5和r6与所述化学式1中的定义相同。L1, L2, R1 to R17, X, a, r5 and r6 are the same as defined in Chemical Formula 1. 6.根据权利要求1所述的化合物,其中,由所述化学式1表示的化合物由下述化学式中的任一个表示:6. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is represented by any one of the following chemical formulas: 在所述化学式中,In the chemical formula, M和Y与所述化学式1中的定义相同。M and Y are the same as defined in Chemical Formula 1. 7.一种感光性树脂组合物,其中,包含权利要求1至6中任一项所述的化合物、粘合剂树脂、多官能性单体、光聚合引发剂、以及溶剂。7 . A photosensitive resin composition comprising the compound according to claim 1 , a binder resin, a polyfunctional monomer, a photopolymerization initiator, and a solvent. 8.根据权利要求7所述的感光性树脂组合物,其中,以所述感光性树脂组合物中的固体成分的总重量为基准,由所述化学式1表示的化合物的含量为5重量%至60重量%,8. The photosensitive resin composition according to claim 7, wherein the content of the compound represented by Chemical Formula 1 is 5 wt % to 60 wt % based on the total weight of the solid components in the photosensitive resin composition. 所述粘合剂树脂的含量为1重量%至60重量%,The content of the binder resin is 1 wt % to 60 wt %, 所述光聚合引发剂的含量为0.1重量%至20重量%,The content of the photopolymerization initiator is 0.1 wt % to 20 wt %. 所述多官能性单体的含量为0.1重量%至50重量%。The content of the multifunctional monomer is 0.1 wt % to 50 wt %. 9.根据权利要求7所述的感光性树脂组合物,其中,还包含添加剂。9 . The photosensitive resin composition according to claim 7 , further comprising an additive. 10.一种感光材料,其利用权利要求7所述的树脂组合物进行制造。10 . A photosensitive material produced using the resin composition according to claim 7 . 11.一种滤色器,其包含权利要求10所述的感光材料。A color filter comprising the photosensitive material according to claim 10 . 12.一种显示装置,其包含权利要求11所述的滤色器。12 . A display device comprising the color filter according to claim 11 .
CN201880084202.5A 2018-04-05 2018-11-12 Xanthene-based compound and photosensitive resin composition containing the same, photosensitive material, color filter, and display device Active CN111527075B (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
KR10-2018-0039901 2018-04-05
KR20180039901 2018-04-05
KR10-2018-0135250 2018-11-06
KR1020180135250A KR102156478B1 (en) 2018-04-05 2018-11-06 Xanthene-based compound photosensitive resin composition, photoresist, color filter, and display device comprising the same
PCT/KR2018/013706 WO2019194384A1 (en) 2018-04-05 2018-11-12 Xanthene-based compound, and photosensitive resin composition, photosensitive material, color filter and display device including same

Publications (2)

Publication Number Publication Date
CN111527075A CN111527075A (en) 2020-08-11
CN111527075B true CN111527075B (en) 2024-03-15

Family

ID=68209448

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201880084202.5A Active CN111527075B (en) 2018-04-05 2018-11-12 Xanthene-based compound and photosensitive resin composition containing the same, photosensitive material, color filter, and display device

Country Status (4)

Country Link
JP (1) JP6940231B2 (en)
KR (1) KR102156478B1 (en)
CN (1) CN111527075B (en)
TW (1) TWI679200B (en)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016047907A (en) * 2014-03-27 2016-04-07 富士フイルム株式会社 Compound, coloring composition, inkjet recording ink, inkjet recording method, inkjet printer cartridge, inkjet recorded matter, color filter, color toner and transfer ink
CN107656423A (en) * 2016-07-26 2018-02-02 株式会社Lg化学 Photosensitive resin composition and color filter containing the photosensitive resin composition
CN107656422A (en) * 2016-07-26 2018-02-02 株式会社Lg化学 Photosensitive resin composition and color filter comprising the photosensitive resin composition
CN107656421A (en) * 2016-07-26 2018-02-02 株式会社Lg化学 Photosensitive resin composition and color filter containing the photosensitive resin composition
CN107743487A (en) * 2015-06-17 2018-02-27 株式会社Lg化学 Xanthene compound and photosensitive resin composition containing same

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20010009058A (en) 1999-07-07 2001-02-05 성재갑 Photosensitive resin composition
JP2012255963A (en) * 2011-06-10 2012-12-27 Sumitomo Chemical Co Ltd Colored photosensitive resin composition
JP5978670B2 (en) * 2012-03-15 2016-08-24 住友化学株式会社 Colored curable resin composition
KR102055478B1 (en) * 2015-09-21 2019-12-12 주식회사 엘지화학 Xanthene-based compound, colorant composition comprising the same and resin composition comprising the same

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016047907A (en) * 2014-03-27 2016-04-07 富士フイルム株式会社 Compound, coloring composition, inkjet recording ink, inkjet recording method, inkjet printer cartridge, inkjet recorded matter, color filter, color toner and transfer ink
CN107743487A (en) * 2015-06-17 2018-02-27 株式会社Lg化学 Xanthene compound and photosensitive resin composition containing same
CN107656423A (en) * 2016-07-26 2018-02-02 株式会社Lg化学 Photosensitive resin composition and color filter containing the photosensitive resin composition
CN107656422A (en) * 2016-07-26 2018-02-02 株式会社Lg化学 Photosensitive resin composition and color filter comprising the photosensitive resin composition
CN107656421A (en) * 2016-07-26 2018-02-02 株式会社Lg化学 Photosensitive resin composition and color filter containing the photosensitive resin composition

Also Published As

Publication number Publication date
KR20190116897A (en) 2019-10-15
JP6940231B2 (en) 2021-09-22
JP2021508746A (en) 2021-03-11
CN111527075A (en) 2020-08-11
TW201943714A (en) 2019-11-16
KR102156478B1 (en) 2020-09-16
TWI679200B (en) 2019-12-11

Similar Documents

Publication Publication Date Title
CN107428715B (en) Xanthene compound, colorant composition containing same, and resin composition containing same
CN107417665B (en) Compound, colorant composition containing the same, and resin composition containing the same
CN111936932B (en) Compound, colorant composition, photosensitive material, color filter and display device
CN107656422A (en) Photosensitive resin composition and color filter comprising the photosensitive resin composition
KR101997656B1 (en) Xanthene-based compound and photosensitive resin composition comprising the same
CN104768925B (en) Styrene-based compounds and their applications in coloring materials, photosensitive resins, photoresist materials, color filters and display devices
CN110546139B (en) Compound, colorant composition containing the same, and resin composition containing the same
KR102331461B1 (en) Compound, photosensitive resin composition comprising the same, photo resist, color filter, and display device
CN107656423A (en) Photosensitive resin composition and color filter containing the photosensitive resin composition
JP6927551B2 (en) Xanthene compounds and photosensitive resin compositions containing them
CN111801620B (en) Photosensitive resin composition, photosensitive material, color filter and display device
KR102690127B1 (en) Compound, colorant composition comprising same, photosensitive resin composition, photosensitive material, color filter, display device comprising same
KR20200034309A (en) Compound and photosensitive resin composition comprising the same, photoresist, color filter and display device
CN111527075B (en) Xanthene-based compound and photosensitive resin composition containing the same, photosensitive material, color filter, and display device
CN111032637B (en) Compound, polymer, coloring material composition, resin composition, color filter and display device
CN110557947B (en) Quinophthalone-based compound, photosensitive resin composition containing the same, photosensitive material, color filter, and display device
CN111971621B (en) Colorant composition, photosensitive material, color filter and display device
CN112204465B (en) Photosensitive resin composition, photosensitive material, color filter and display device
KR102268234B1 (en) Compound, colorant composition, photosensitive resin composition, photoresist, color filter, and display device
CN112204466B (en) Photosensitive resin composition, photosensitive material, color filter and display device
KR102718652B1 (en) Compound, photosensitive resin composition comprising the same, photoresist, color filter and display device
KR102306981B1 (en) Xanthene-based compound, color material composition comprising the same, photosensitive resin composition, photoresist, color filter, and display device
KR20190140747A (en) Compound, photosensitive resin composition comprising the same, photo resist, color filter, and display device
KR20200143927A (en) Compound, photosensitive resin composition comprising same, photosensitive material, color filter and display device
KR20200137750A (en) Compound, photosensitive resin composition comprising same, photosensitive material, color filter and display device

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant