TWI657116B - Coloring resin composition, and color filter and display device using the same - Google Patents

Coloring resin composition, and color filter and display device using the same Download PDF

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TWI657116B
TWI657116B TW106144560A TW106144560A TWI657116B TW I657116 B TWI657116 B TW I657116B TW 106144560 A TW106144560 A TW 106144560A TW 106144560 A TW106144560 A TW 106144560A TW I657116 B TWI657116 B TW I657116B
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group
resin composition
substituted
hydrogen atom
atom
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TW201927911A (en
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辻内翔
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住華科技股份有限公司
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    • 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
    • G03F7/027Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • 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

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  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optical Filters (AREA)
  • Materials For Photolithography (AREA)

Abstract

一種著色樹脂組成物、及應用其之彩色濾光片和顯示裝置。著色樹脂組成物包括著色劑、樹脂、光聚合單體、光聚合起始劑以及溶劑。所述著色劑包括染料,所述染料包括具有如化學式1所示的結構的化合物: A colored resin composition, and a color filter and a display device using the same. The colored resin composition includes a colorant, a resin, a photopolymerizable monomer, a photopolymerization initiator, and a solvent. The colorant includes a dye including a compound having a structure shown in Chemical Formula 1:

Description

著色樹脂組成物、及應用其之彩色濾光片和顯示 裝置 Colored resin composition, color filter and display using the same Device

本揭露是關於一種著色樹脂組成物。本揭露也關於一種由所述著色樹脂組成物所形成的彩色濾光片。本揭露還關於一種包括所述彩色濾光片的顯示裝置。 This disclosure relates to a colored resin composition. The present disclosure also relates to a color filter formed from the colored resin composition. The disclosure also relates to a display device including the color filter.

在顯示器中,普遍地使用彩色濾光片來控制各畫素的顏色。舉例來說,在較早期的液晶顯示器中,彩色濾光片被形成在相對於薄膜電晶體基板的基板上,其通常被稱為彩色濾光片基板。彩色濾光片的光阻結構可以使用樹脂組成物來形成。一般來說,為了配合各種類型的顯示器應用,著色樹脂組成物的成分的可加以調整和最佳化。 In a display, a color filter is commonly used to control the color of each pixel. For example, in earlier liquid crystal displays, a color filter was formed on a substrate opposite to a thin film transistor substrate, which is often referred to as a color filter substrate. The photoresist structure of the color filter can be formed using a resin composition. Generally, the composition of the colored resin composition can be adjusted and optimized to match various types of display applications.

本揭露係有關於一種著色樹脂組成物、及應用其之彩色濾光片和顯示裝置。實施例之著色樹脂組成物具有良好的耐熱性。 This disclosure relates to a colored resin composition, and a color filter and a display device using the same. The colored resin composition of the examples has good heat resistance.

根據本揭露之一實施例,提出一種著色樹脂組成物。著色樹脂組成物包括著色劑、樹脂、光聚合單體、光聚合起始劑以及溶 劑。所述著色劑包括染料,所述染料包括具有如化學式1所示的結構的化合物: According to an embodiment of the present disclosure, a colored resin composition is provided. The colored resin composition includes a colorant, a resin, a photopolymerizable monomer, a photopolymerization initiator, and a solvent. The colorant includes a dye including a compound having a structure shown in Chemical Formula 1:

其中R11和R12各自獨立表示氫原子、取代或未取代的烷基、或取代或未取代的芳香基,且R11和R12的至少其中之一包括C-C雙鍵,R21表示氫原子、取代或未取代的烷基、或取代或未取代的芳香基,R31至R38各自獨立表示氫原子、鹵原子、取代或未取代的烷基、取代或未取代的芳香基、氰(cyano)基、硝(nitro)基、磺醯基或羥基,R41至R44各自獨立表示氫原子、取代或未取代的烷基、或取代或未取代的芳香基,且R41至R44的至少其中之一包括C-C雙鍵,且R41與R42和/或R43與R44可鍵結形成環狀結構,X表示硫原子,An表示陰離子,m表示1以上的正整數,a表示1以上的正整數,且m=a。 R11 and R12 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic group, and at least one of R11 and R12 includes a CC double bond, and R21 represents a hydrogen atom, substituted or unsubstituted R31 to R38 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, a cyano group, or a nitro group. ) Group, sulfonyl group or hydroxyl group, R41 to R44 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic group, and at least one of R41 to R44 includes a CC double bond, and R41 and R42 and / or R43 and R44 may be bonded to form a cyclic structure, X represents a sulfur atom, An represents an anion, m represents a positive integer of 1 or more, a represents a positive integer of 1 or more, and m = a.

根據本揭露之另一實施例,提出一種彩色濾光片。此彩色濾光片由例如是前述的著色樹脂組成物所形成。 According to another embodiment of the present disclosure, a color filter is provided. This color filter is formed of, for example, the aforementioned colored resin composition.

根據本揭露之更一實施例,提出一種顯示裝置。此顯示裝置包括例如是前述的彩色濾光片。 According to a further embodiment of the present disclosure, a display device is provided. This display device includes, for example, the aforementioned color filter.

為了對本揭露之上述及其他方面有更佳的瞭解,下文特舉實施例,作詳細說明如下: In order to have a better understanding of the above and other aspects of this disclosure, the following specific examples are described in detail below:

以下係提出各種實施例進行詳細說明,實施例僅用以作為範例說明,並不會限縮本揭露欲保護之範圍,本揭露仍可採用其他特徵、元件、方法及參數來加以實施。實施例的提出,僅係用以例示本揭露的技術特徵,並非用以限定本揭露的申請專利範圍。該技術領域中具有通常知識者,將可根據以下說明書的描述,在不脫離本揭露的精神範圍內,作均等的修飾與變化。 The following is a detailed description of various embodiments. The embodiments are only used as examples, and do not limit the scope of the disclosure. The disclosure can still be implemented by using other features, components, methods and parameters. The proposal of the embodiments is only used to exemplify the technical features of the disclosure, and is not intended to limit the scope of patent application of the disclosure. Those with ordinary knowledge in this technical field will be able to make equal modifications and changes within the scope of the present disclosure without departing from the spirit of the present disclosure, as described in the following description.

本揭露的一些實施例是關於一種著色樹脂組成物。此種著色樹脂組成物包括著色劑(A)、樹脂(B)、光聚合單體(C)、光聚合起始劑(D)、和溶劑(E)。其中,著色劑(A)包括染料,染料包括具有如化學式1所示的結構的化合物:[化學式1] Some embodiments of the present disclosure relate to a colored resin composition. Such a colored resin composition includes a colorant (A), a resin (B), a photopolymerizable monomer (C), a photopolymerization initiator (D), and a solvent (E). Wherein, the colorant (A) includes a dye, and the dye includes a compound having a structure as shown in Chemical Formula 1: [Chemical Formula 1]

其中R11和R12各自獨立表示氫原子、取代或未取代的烷基、或取代或未取代的芳香基,且R11和R12的至少其中之一包括C-C雙鍵,R21表示氫原子、取代或未取代的烷基、或取代或未取代的芳香基,R31至R38各自獨立表示氫原子、鹵原子、取代或未取代的烷基、取代或未取代的芳香基、氰(cyano)基、硝(nitro)基、磺醯基或羥基,R41至R44各自獨立表示氫原子、取代或未取代的烷基、或取代或未取代的芳香基,且R41至R44的至少其中之一包括C-C雙鍵,且R41與R42和/或R43與R44可鍵結形成環狀結構,X表示硫原子,An表示陰離子,m表示1以上的正整數,a表示1以上的正整數,且m=a。 R11 and R12 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic group, and at least one of R11 and R12 includes a CC double bond, and R21 represents a hydrogen atom, substituted or unsubstituted R31 to R38 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, a cyano group, or a nitro group. ) Group, sulfonyl group or hydroxyl group, R41 to R44 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic group, and at least one of R41 to R44 includes a CC double bond, and R41 and R42 and / or R43 and R44 may be bonded to form a cyclic structure, X represents a sulfur atom, An represents an anion, m represents a positive integer of 1 or more, a represents a positive integer of 1 or more, and m = a.

在此,所述著色劑(A)、樹脂(B)、光聚合單體(C)、光聚合起始劑(D)和溶劑(E)等成分用詞,獨立地可包括單一種或多種著 色劑(A)、樹脂(B)、光聚合單體(C)、光聚合起始劑(D)和溶劑(E)等該成分的情況。 Here, the terms such as the colorant (A), the resin (B), the photopolymerizable monomer (C), the photopolymerization initiator (D), and the solvent (E) may independently include a single or a plurality With In the case of such components as a toner (A), a resin (B), a photopolymerizable monomer (C), a photopolymerization initiator (D), and a solvent (E).

根據一些實施例,如前述化學式1所示的結構的化合物中,R11和R12不包括酯基。 According to some embodiments, in the compound having the structure shown in the aforementioned Chemical Formula 1, R11 and R12 do not include an ester group.

根據本揭露的實施例的著色樹脂組成物,由於R11和R12的至少其中之一包括不飽和C-C雙鍵,使染料中的如前述化學式1所示的結構的化合物可進一步和樹脂(B)交聯聚合,而形成交聯度較高而較堅固的樹脂結構,而能夠使得形成在樹脂結構中的染料具有較高的耐熱性,能夠較佳地固定於樹脂(B)的交聯結構中,可以避免後續的熱製程對於著色樹脂組成物造成破壞,進而達到著色樹脂組成物製成的彩色濾光片可同時具有良好耐熱性及高亮度的效果。 According to the colored resin composition according to the embodiment of the present disclosure, since at least one of R11 and R12 includes an unsaturated CC double bond, the compound having the structure shown in the aforementioned Chemical Formula 1 in the dye can further cross-link with the resin (B). Cross-linking polymerization to form a resin structure with a higher degree of cross-linking and a stronger resin structure, which can make the dye formed in the resin structure have higher heat resistance and can be better fixed in the cross-linked structure of the resin (B), It is possible to avoid the subsequent thermal process from damaging the colored resin composition, and further to achieve the effect that the color filter made of the colored resin composition can have good heat resistance and high brightness at the same time.

根據一些實施例,具有如化學式1所示的結構的化合物佔所述著色樹脂組成物的約1~7wt%。 According to some embodiments, the compound having a structure as shown in Chemical Formula 1 accounts for about 1 to 7 wt% of the colored resin composition.

根據一些實施例,染料更可包括具有如化學式2所示的結構的化合物:[化學式2] According to some embodiments, the dye may further include a compound having a structure as shown in Chemical Formula 2: [Chemical Formula 2]

其中R21至R24各自獨立表示氫原子、C1至C10的烷基、或取代的芳香基,該C1至C10的烷基中所含的氫原子可由鹵原子取代,且該烷基中所含的CH2-亦可由-O-、-CO-、-NR11-、-OCO-、-COO-、-OCONH-、-CONH-或是-NHCO-所取代,但烷基中所含的鄰接的-CH2-不會同時被取代、末端的-CH2-也不會被取代,R25及R26各自獨立地表示氫原子或C1至C6的烷基,R27及R28各自獨立地表示-OH、-SO3 -、-SO3H、-SO3 -Z+、-CO2 -、-CO2H、-CO2 -Z+、-CO2R10、-SO3R10或是-SO2NR11R12,Y表示陰離子,R10為C1至C20的烷基、該烷基所含之氫原子可由鹵原子取代,Z++N(R13)4、Na+或是K+,R11、R12及R13各自獨立地表示氫原子、或C1至C20的烷基,p表示0~4的整數。 R21 to R24 each independently represent a hydrogen atom, a C1 to C10 alkyl group, or a substituted aromatic group. The hydrogen atom contained in the C1 to C10 alkyl group may be substituted by a halogen atom, and the CH contained in the alkyl group 2 -Can also be replaced by -O-, -CO-, -NR11-, -OCO-, -COO-, -OCONH-, -CONH-, or -NHCO-, but the adjacent -CH contained in the alkyl group 2 -will not be substituted at the same time, and the terminal -CH 2 -will not be substituted, R25 and R26 each independently represent a hydrogen atom or an alkyl group of C1 to C6, and R27 and R28 each independently represent -OH, -SO 3 -, -SO 3 H, -SO 3 - Z +, -CO 2 -, -CO 2 H, -CO 2 - Z +, -CO 2 R 10, -SO 3 R10 or -SO 2 NR11R12, Y represents Anion, R10 is an alkyl group of C1 to C20, a hydrogen atom contained in the alkyl group may be substituted by a halogen atom, Z + is + N (R13) 4 , Na + or K + , and R11, R12 and R13 each independently represent A hydrogen atom or a C1 to C20 alkyl group, and p represents an integer of 0 to 4.

根據一些實施例,舉例而言,染料更可包括具有如化學式3所示的結構的化合物:[化學式3] According to some embodiments, for example, the dye may further include a compound having a structure as shown in Chemical Formula 3: [Chemical Formula 3]

其中R1~R4各自獨立地表示氫原子、一R8或碳數6~10的一價芳香族烴基,或者R1和R2、以及R3和R4各自一起形成包含氮原子的環,該芳香族烴基中包含的氫原子可以經鹵原子、一R8、一OH、一OR8、一SO3 -、一SO3H、一SO3 -M+、一CO2H、一CO2R8、一SO3R8或一SO2NR9R10取代;R5表示一OH、一SO3 -、一SO3H、一SO3M+、一CO2H、一CO2M+、一CO2R8、一SO3R8或一SO2NR9R10;n表示0~5的整數。在n為2以上的整數的情況下,多個R5可以相同也可以相互不同;R6和R7各自獨立地表示氫原子或碳數1~6的烷基;M+表示+N(R11)4、Na+或K+,W表示鹵原子;R8表示碳數1~20的一價飽和烴基,該飽和烴基中包含的氫原子可以經碳數6~10的芳香族烴基或鹵原子取代,該飽和烴基中包含的一CH2-可以被一S-、一O-、一CO一或一NR11-置換;R11表示氫原子、碳數1~20的一價飽和烴基或碳數7~10的芳烷基,在存在多個R11的情況下,它們的全部或一部分可以相同;R9和R10各自獨立地表示氫原子、或碳數1~20的一價飽和烴基,該飽和烴 基中包含的氫原子可以經一OH或鹵原子取代,該飽和脂肪族烴基中包含的一CH2-可以被一S-、一O-、一CO-、一NH-或一NR8-置換,R9和R10可以相互鍵合而形成包含氮原子的3~10元環的雜環;鹵原子係為氟原子、氯原子、溴原子或碘原子,b表示1以上的正整數。 R1 to R4 each independently represent a hydrogen atom, one R8 or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms, or R1 and R2, and R3 and R4 each together form a ring containing a nitrogen atom, and the aromatic hydrocarbon group contains the hydrogen atoms may be by a halogen atom, an R8, an OH, a OR8, a SO 3 -, a SO 3 H, a SO 3 - M +, a CO 2 H, a CO 2 R8, a SO 3 R8 or a SO 2 NR9R10 substituent; R5 represents an OH, a SO 3 -, a SO 3 H, a SO 3 M +, a CO 2 H, a CO 2 M +, a CO 2 R8, a SO 3 R8 or a SO 2 NR9R10; n represents an integer from 0 to 5. When n is an integer of 2 or more, a plurality of R5 may be the same or different from each other; R6 and R7 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; M + represents + N (R11) 4 , Na + or K + , W represents a halogen atom; R8 represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with an aromatic hydrocarbon group or halogen atom having 6 to 10 carbon atoms, and the saturated One CH 2 -contained in a hydrocarbon group may be replaced by one S-, one O-, one CO one, or one NR11-; R11 represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aromatic group having 7 to 10 carbon atoms. In the case of multiple R11 alkyl groups, all or part of them may be the same; R9 and R10 each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group It may be substituted by an OH or a halogen atom. One CH 2 -contained in the saturated aliphatic hydrocarbon group may be replaced by one S-, one O-, one CO-, one NH- or one NR8-, and R9 and R10 may be bonded to each other. Combined to form a 3 to 10 membered heterocyclic ring containing a nitrogen atom; the halogen atom is a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and b represents a positive integer of 1 or more.

根據一些實施例,舉例而言,前述具有如化學式3所示的結構的化合物例如可以是具有如化學式3-1所示的結構的化合物(A-4): According to some embodiments, for example, the aforementioned compound having a structure as shown in Chemical Formula 3 may be, for example, a compound (A-4) having a structure as shown in Chemical Formula 3-1:

根據一些實施例,舉例而言,染料可包括具有如化學式4所示的結構的化合物(A-2): According to some embodiments, for example, the dye may include a compound (A-2) having a structure as shown in Chemical Formula 4:

根據一些實施例,具有如化學式4所示的結構的化合物(A-2)佔所述著色樹脂組成物的約0.01~10wt%。 According to some embodiments, the compound (A-2) having a structure as shown in Chemical Formula 4 accounts for about 0.01 to 10 wt% of the colored resin composition.

根據一些實施例,舉例而言,染料可包括具有如化學式5所示的結構的化合物(A-3): According to some embodiments, for example, the dye may include a compound (A-3) having a structure as shown in Chemical Formula 5:

根據一些實施例,具有如化學式5所示的結構的化合物(A-3)佔所述著色樹脂組成物的約0.01~10wt%。 According to some embodiments, the compound (A-3) having a structure as shown in Chemical Formula 5 accounts for about 0.01 to 10 wt% of the colored resin composition.

根據一些實施例,樹脂(B)可包括鹼溶性樹脂,例如是但不限於具有(甲基)丙烯酸衍生之結構單元。舉例而言,樹脂(B)可包括具有如化學式6所示的結構的樹脂(B-1): According to some embodiments, the resin (B) may include an alkali-soluble resin, such as, but not limited to, a structural unit having (meth) acrylic acid-derived structural units. For example, the resin (B) may include a resin (B-1) having a structure as shown in Chemical Formula 6:

根據一些實施例,光聚合單體(C)為可藉由光聚合引發劑(D)產生的活性自由基及/或酸而聚合的單體,例如是但不限於具有可聚合性的乙烯性不飽和鍵,像是(甲基)丙烯酸酯化合物。在此,使用括號來敘述的化合物,意味著包括括號內文字存在與不存在的情況,例如前述的(甲基)丙烯酸酯化合物,囊括丙烯酸酯化合物、和甲基丙烯酸酯化合物的情形。舉例來說,光聚合單體(C)可包括但不受限於選自於由下列選項所組成的群組中的至少一者:丙烯酸壬基苯基卡必醇酯、丙烯酸2-羥基-3-苯氧基丙酯、丙烯酸2-乙基己基卡必醇酯、丙烯酸2-羥基乙酯、N-乙烯基吡咯酮等具有一個乙烯性不飽和鍵的聚合性化合物;二(甲基)丙烯酸1,6-己烷二醇酯、二(甲基)丙烯酸乙二醇酯、二(甲基)丙烯酸新戊二醇酯、二(甲基)丙烯酸三乙二醇酯、雙酚A的雙(丙烯醯氧基乙基)醚、二(甲基)丙烯酸3-甲基戊烷二醇酯等具有二個乙烯性不飽和鍵的聚合性化合物;以及三(甲基)丙烯酸三羥甲基丙烷酯、三(甲基)丙烯酸季戊四醇酯、四(甲基)丙烯酸季戊四醇酯、五(甲基)丙烯酸二季戊四醇酯、六(甲基)丙烯酸二季戊四醇酯、八(甲基)丙烯酸三季戊四醇酯、三季戊四醇七(甲基)丙烯酸酯、十(甲基)丙烯酸四季戊四醇酯、九(甲基)丙烯酸四季戊四醇酯、三(2-(甲基)丙烯醯氧基乙基)異氰酸酯、四(甲基)丙烯酸乙二醇改性季戊四醇酯、六(甲基)丙烯酸乙二醇改性二季戊四醇酯、四(甲基)丙烯酸丙二醇改性季戊四醇酯、六(甲基)丙烯酸丙二醇改性二季戊四醇酯、四(甲基)丙烯酸己內酯改性季戊四醇酯、六(甲基)丙烯酸己內酯改性二季戊四醇酯等具有三 個乙烯性不飽和鍵的聚合性化合物。在一些實施方案中,光聚合單體(C)較佳地為具有三個乙烯性不飽和鍵的聚合性化合物。 According to some embodiments, the photopolymerizable monomer (C) is a monomer that can be polymerized by living radicals and / or acids generated by the photopolymerization initiator (D), such as, but not limited to, a polymerizable ethylenic Unsaturated bonds, like (meth) acrylate compounds. Here, the compounds described using parentheses are meant to include the presence or absence of the characters in the parentheses, for example, the aforementioned (meth) acrylate compounds include acrylate compounds and methacrylate compounds. For example, the photopolymerizable monomer (C) may include, but is not limited to, at least one selected from the group consisting of nonylphenyl carbitol acrylate, 2-hydroxy-acrylate Polymerizable compounds with one ethylenically unsaturated bond, such as 3-phenoxypropyl ester, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, and N-vinylpyrrolidone; bis (methyl) 1,6-hexanediol acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, bisphenol A Polymerizable compounds having two ethylenically unsaturated bonds, such as bis (propenyloxyethyl) ether and 3-methylpentanediol di (meth) acrylate; and trimethylol tri (meth) acrylate Propane, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tripentaerythritol octa (meth) acrylate Ester, tripentaerythritol hepta (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tetrapentaerythritol nine (meth) acrylate Ester, tris (2- (meth) acryloxyethyl) isocyanate, ethylene glycol tetra (meth) acrylate modified pentaerythritol, ethylene glycol hexa (meth) acrylate modified dipentaerythritol, tetra ( Propylene glycol methacrylate modified pentaerythritol acrylate, propylene glycol hexa (meth) acrylate modified dipentaerythritol ester, caprolactone tetra (meth) acrylate modified pentaerythritol ester, caprolactone hexa (meth) acrylate modified dipentaerythritol Esters etc. have three Polymerizable compound with ethylenically unsaturated bonds. In some embodiments, the photopolymerizable monomer (C) is preferably a polymerizable compound having three ethylenically unsaturated bonds.

根據一些實施例,光聚合起始劑(D)可為任何能夠藉由光或熱的作用而產生活性自由基、酸等,進而使得聚合開始的化合物。舉例來說,光聚合起始劑(D)可包括但不受限於選自於由下列選項所組成的群組中的至少一者:O-醯基肟(O-acyloxime)化合物、烷基苯基酮化合物、雙咪唑化合物、三嗪化合物、醯基膦氧化物(acyl phosphine oxide)、安息香化合物、二苯基酮化合物、醌系化合物、10-丁基-2-氯吖啶酮、苄基、苯基甲醯甲酸甲酯、和環戊二烯鈦(titanocene)化合物。在一些實施方案中,光聚合引發劑(D)較佳地包括選自於由下列選項所組成的群組中的至少一者:O-醯基肟化合物、烷基苯基酮化合物、雙咪唑化合物、三嗪化合物、和醯基膦氧化物。舉例來說,在以O-醯基肟化合物作為光聚合引發劑(D)的情況,可使用Irgacure® OXE-01(BASF公司)、Irgacure® OXE-02(BASF公司)、N-1919(ADEKA公司)等市售商品。 According to some embodiments, the photopolymerization initiator (D) may be any compound capable of generating living radicals, acids, and the like through the action of light or heat, thereby starting the polymerization. For example, the photopolymerization initiator (D) may include, but is not limited to, at least one selected from the group consisting of an O-acyloxime compound, an alkyl group Phenyl ketone compound, bisimidazole compound, triazine compound, acyl phosphine oxide, benzoin compound, diphenyl ketone compound, quinone compound, 10-butyl-2-chloroacridone, benzyl Compounds, methyl phenylformamate, and titanocene compounds. In some embodiments, the photopolymerization initiator (D) preferably includes at least one selected from the group consisting of an O-fluorenyl oxime compound, an alkyl phenone compound, and bisimidazole Compounds, triazine compounds, and fluorenylphosphine oxides. For example, when an O-fluorenyl oxime compound is used as the photopolymerization initiator (D), Irgacure® OXE-01 (BASF), Irgacure® OXE-02 (BASF), N-1919 (ADEKA) Companies) and other commercially available products.

根據一些實施例,溶劑(E)可包括但不受限於選自於由下列選項所組成的群組中的至少一者:酯溶劑(在此意指於分子中含有-COO-但不含-O-的溶劑)、醚溶劑(在此意指於分子中含有-O-但不含-COO-的溶劑)、醚酯溶劑(在此意指於分子中含有-COO-及-O-的溶劑)、酮溶劑(在此意指於分子中含有-CO-但不含-COO-的溶劑)、醇溶劑(在此意指於分子中含有OH但不含-O-、-CO-及-COO-的溶劑)、芳香族烴溶劑、醯胺溶劑、二甲基亞碸等。 According to some embodiments, the solvent (E) may include, but is not limited to, at least one selected from the group consisting of: an ester solvent (herein means that the molecule contains -COO- but does not contain -O-solvent), ether solvents (referred to herein as solvents containing -O- but not -COO-), ether ester solvents (referred to herein as containing -COO- and -O- Solvents), ketone solvents (here means solvents containing -CO- but not -COO- in the molecule), alcohol solvents (here means solvent containing OH but -O-, -CO- And -COO- solvents), aromatic hydrocarbon solvents, amidine solvents, dimethyl sulfene and the like.

一些實施例中,著色樹脂組成物的固含量約10~25wt%,較佳地約為14~18wt%;著色劑(A)佔著色樹脂組成物的固成分的約10~40wt%,較佳地約為11~30wt%;染料佔著色劑(A)的約1~100wt%,較佳地約為5~95wt%。基於上述,染料佔著色樹脂組成物的約0.01~10wt%。 In some embodiments, the solid content of the colored resin composition is about 10 to 25 wt%, preferably about 14 to 18 wt%; the colorant (A) accounts for about 10 to 40 wt% of the solid content of the colored resin composition, preferably The ground is about 11 to 30 wt%; the dye accounts for about 1 to 100 wt% of the colorant (A), preferably about 5 to 95 wt%. Based on the above, the dye accounts for about 0.01 to 10% by weight of the colored resin composition.

一些實施例中,樹脂(B)佔著色樹脂組成物的約2~10wt%,光聚合單體(C)佔著色樹脂組成物的約2~10wt%,光聚合起始劑(D)佔著色樹脂組成物的約0.1~2.5wt%,溶劑(E)佔著色樹脂組成物的約75~90wt%。 In some embodiments, the resin (B) accounts for about 2 to 10 wt% of the colored resin composition, the photopolymerization monomer (C) accounts for about 2 to 10 wt%, and the photopolymerization initiator (D) accounts for coloration. About 0.1 to 2.5 wt% of the resin composition, and the solvent (E) accounts for about 75 to 90 wt% of the colored resin composition.

根據一些實施例,著色樹脂組成物還可包括調平劑、聚合起始助劑、填充劑、密著促進劑、抗氧化劑、光安定劑、鏈移動劑等其他添加劑,但不受限於此。 According to some embodiments, the colored resin composition may further include, but is not limited to, other additives such as a leveling agent, a polymerization initiation aid, a filler, an adhesion promoter, an antioxidant, a light stabilizer, a chain shifting agent, and the like. .

本揭露的另一實施例是關於一種彩色濾光片,其可由根據前述任一實施例的著色樹脂組成物所形成。舉例來說,根據前述任一實施例的著色樹脂組成物可藉由光微影法、噴墨法、或印刷法等方法形成所述彩色濾光片,但不受限於此。 Another embodiment of the present disclosure relates to a color filter, which may be formed of the colored resin composition according to any one of the foregoing embodiments. For example, the colored resin composition according to any one of the foregoing embodiments may form the color filter by a photolithography method, an inkjet method, or a printing method, but is not limited thereto.

本揭露的再一實施例是關於一種顯示裝置,其可包括前述的彩色濾光片,但不受限於此。根據一些實施例,所述顯示裝置可為液晶顯示裝置、電致發光顯示裝置、或電漿顯示裝置等顯示器。 Yet another embodiment of the present disclosure relates to a display device, which may include the aforementioned color filter, but is not limited thereto. According to some embodiments, the display device may be a display such as a liquid crystal display device, an electroluminescent display device, or a plasma display device.

以下,本揭露將提供數個實施例和比較例,以更具體地說明根據本揭露實施例的著色樹脂組成物可達成的功效。 Hereinafter, the present disclosure will provide several examples and comparative examples to more specifically explain the effect that the colored resin composition can achieve according to the examples of the present disclosure.

[實施例1~6] [Examples 1 to 6]

使用前述具有如化學式1所示的結構的化合物(化合物A-2、化合物A-3、化合物A-4)之染料作為著色劑(A),且使用前述樹脂(B-1)。使用六(甲基)丙烯酸二季戊四醇酯(DPHA)(日本化藥)作為光聚合單體。使用Irgacure® OXE-01(BASF公司)作為光聚合引發劑。使用丙二醇甲醚醋酸酯(PGMEA)作為溶劑。使用聚酯改質矽油SH8400(道康寧東麗公司)作為調平劑。以表1所列示的比例配製成著色樹脂組成物。將配製完成的著色樹脂組成物以旋塗法塗佈於5公分*5公分的玻璃基板(Eagle2000,Corning公司)上。於100℃預烘烤3分鐘。放置冷卻後,使用曝光機(TME-150RSK,TOPCON(股)製)於大氣環境氣氛下以80mJ/cm2的曝光量(365nm基準)進行光照射,且並未使用光罩。接著在烘箱中於230℃後烘烤30分鐘,得到彩色濾光片的樣品(膜厚2.5μm),並對此樣品測定亮度及色度。將前述製備完成之彩色濾光片(玻璃)樣品量測色度後,接著在烘箱中於230℃後再烘烤120分鐘,再度以色度機量測彩色濾光片(玻璃)樣品之色度,並且計算第二次烘烤前後的色度之△Eab。(△Eab=((L*-L*)^2+(a*-a*)^2+(b*-b*)^2)^(1/2)) As the colorant (A), a dye of the aforementioned compound (Compound A-2, Compound A-3, Compound A-4) having a structure shown in Chemical Formula 1 is used, and the aforementioned resin (B-1) is used. As the photopolymerizable monomer, dipentaerythritol hexa (meth) acrylate (DPHA) (Japanese chemical) was used. Irgacure® OXE-01 (BASF) was used as a photopolymerization initiator. As the solvent, propylene glycol methyl ether acetate (PGMEA) was used. Polyester modified silicone oil SH8400 (Dow Corning Toray) was used as a leveling agent. The colored resin composition was formulated at the ratios shown in Table 1. The prepared colored resin composition was applied to a glass substrate (Eagle2000, Corning) of 5 cm by 5 cm by a spin coating method. Pre-bake at 100 ° C for 3 minutes. After being left to cool, light exposure was performed using an exposure machine (TME-150RSK, manufactured by TOPCON Co., Ltd.) at an exposure of 80 mJ / cm 2 (based on a 365 nm standard) in an atmospheric environment, and a photomask was not used. Then, after baking in an oven at 230 ° C. for 30 minutes, a sample (film thickness: 2.5 μm) of a color filter was obtained, and the brightness and chromaticity of the sample were measured. After measuring the chromaticity of the prepared color filter (glass) sample, then baking it in an oven at 230 ° C for another 120 minutes, and then measuring the color of the color filter (glass) sample with a colorimeter. And calculate the ΔEab of the chromaticity before and after the second baking. (△ Eab = ((L * -L *) ^ 2+ (a * -a *) ^ 2+ (b * -b *) ^ 2) ^ (1/2))

[比較例1~3] [Comparative Examples 1 to 3]

使用具有如以下化學式所示的結構的化合物(A-1)之染料作為著色劑。 As the colorant, a dye of the compound (A-1) having a structure represented by the following chemical formula is used.

其他條件如前述實施例。依照實施例所述的方法製成樣品並進行觀察。 The other conditions are the same as the foregoing embodiments. Samples were made according to the method described in the examples and observed.

[結果和評價] [Results and evaluations]

各實施例和比較例的成分比例(重量百分比)和色度觀察結果如表1所列,「Bx」和「By」表示對樣品測定亮度時的色度座標,△Eab的數值越大表示耐熱性越差。如表1所示,各個由實施例的著色樹脂組成物所形成的彩色濾光片的樣品,皆具有良好耐熱性及高亮度。 The composition ratio (weight percentage) and color observation results of each example and comparative example are listed in Table 1. "Bx" and "By" represent the chromaticity coordinates when measuring the brightness of the sample. The worse the sex. As shown in Table 1, each of the color filter samples formed of the colored resin composition of the examples had good heat resistance and high brightness.

綜上所述,雖然本揭露已以實施例揭露如上,然其並非用以限定本揭露。本揭露所屬技術領域中具有通常知識者,在不脫離本揭露之精神和範圍內,當可作各種之更動與潤飾。因此,本揭露之保護範圍當視後附之申請專利範圍所界定者為準。 In summary, although the present disclosure has been disclosed above by way of example, it is not intended to limit the present disclosure. Those with ordinary knowledge in the technical field to which this disclosure pertains can make various changes and modifications without departing from the spirit and scope of this disclosure. Therefore, the scope of protection of this disclosure shall be determined by the scope of the appended patent application.

Claims (7)

一種著色樹脂組成物,包括:著色劑,包括染料,所述染料包括具有如化學式1所示的結構的化合物:其中R11和R12各自獨立表示氫原子、取代或未取代的烷基、或取代或未取代的芳香基,且R11和R12的至少其中之一包括C-C雙鍵,R21表示氫原子、取代或未取代的烷基、或取代或未取代的芳香基,R31至R38各自獨立表示氫原子、鹵原子、取代或未取代的烷基、取代或未取代的芳香基、氰(cyano)基、硝(nitro)基、磺醯基或羥基,R41至R44各自獨立表示氫原子、取代或未取代的烷基、或取代或未取代的芳香基,且R41至R44的至少其中之一包括C-C雙鍵,且R41與R42和/或R43與R44可鍵結形成環狀結構,X表示硫原子,An表示陰離子,m表示1以上的正整數,a表示1以上的正整數,且m=a;樹脂;光聚合單體;光聚合起始劑;以及溶劑,其中所述著色劑佔所述著色樹脂組成物的10~40wt%,所述染料佔所述著色劑的1~100wt%,所述樹脂佔所述著色樹脂組成物的2~10wt%,所述光聚合單體佔所述著色樹脂組成物的2~10wt%,所述光聚合起始劑佔所述著色樹脂組成物的0.1~2.5wt%,所述溶劑佔所述著色樹脂組成物的75~90wt%。A colored resin composition includes: a colorant including a dye, the dye including a compound having a structure shown in Chemical Formula 1: R11 and R12 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic group, and at least one of R11 and R12 includes a CC double bond, and R21 represents a hydrogen atom, substituted or unsubstituted R31 to R38 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, a cyano group, or a nitro group. ) Group, sulfonyl group or hydroxyl group, R41 to R44 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic group, and at least one of R41 to R44 includes a CC double bond, and R41 and R42 and / or R43 and R44 may be bonded to form a cyclic structure, X represents a sulfur atom, An represents an anion, m represents a positive integer of 1 or more, a represents a positive integer of 1 or more, and m = a; resin; light A polymerization monomer; a photopolymerization initiator; and a solvent, wherein the colorant accounts for 10 to 40% by weight of the coloring resin composition, the dye accounts for 1 to 100% by weight of the colorant, and the resin accounts for 2 to 10% by weight of the colored resin composition, and the photopolymerizable monomer accounts for the colored tree 2 to 10% by weight of the fat composition, the photopolymerization initiator accounts for 0.1 to 2.5% by weight of the colored resin composition, and the solvent accounts for 75 to 90% by weight of the colored resin composition. 如申請專利範圍第1項所述之著色樹脂組成物,其中R11和R12不包括酯基。The colored resin composition according to item 1 of the scope of patent application, wherein R11 and R12 do not include an ester group. 如申請專利範圍第1項所述之著色樹脂組成物,其中所述染料更包括具有如化學式2所示的結構的化合物:[化學式2]其中R21至R24各自獨立表示氫原子、C1至C10的烷基、或取代的芳香基,該C1至C10的烷基中所含的氫原子可由鹵原子取代,且該烷基中所含的CH2-亦可由-O-、-CO-、-NR11-、-OCO-、-COO-、-OCONH-、-CONH-或是-NHCO-所取代,但烷基中所含的鄰接的-CH2-不會同時被取代、末端的-CH2-也不會被取代,R25及R26各自獨立地表示氫原子或C1至C6的烷基,R27及R28各自獨立地表示-OH、-SO3 -、-SO3H、-SO3 -Z+、-CO2 -、-CO2H、-CO2 -Z+、-CO2R10、-SO3R10或是-SO2NR11R12,Y表示陰離子,R10為C1至C20的烷基、該烷基所含之氫原子可由鹵原子取代,Z++N(R13)4、Na+或是K+,R11、R12及R13各自獨立地表示氫原子、或C1至C20的烷基,p表示0~4的整數。The colored resin composition according to item 1 of the scope of patent application, wherein the dye further includes a compound having a structure as shown in Chemical Formula 2: [Chemical Formula 2] R21 to R24 each independently represent a hydrogen atom, a C1 to C10 alkyl group, or a substituted aromatic group. The hydrogen atom contained in the C1 to C10 alkyl group may be substituted by a halogen atom, and the CH contained in the alkyl group 2 -Can also be replaced by -O-, -CO-, -NR11-, -OCO-, -COO-, -OCONH-, -CONH-, or -NHCO-, but the adjacent -CH contained in the alkyl group 2 -will not be substituted at the same time, and the terminal -CH 2 -will not be substituted, R25 and R26 each independently represent a hydrogen atom or an alkyl group of C1 to C6, and R27 and R28 each independently represent -OH, -SO 3 -, -SO 3 H, -SO 3 - Z +, -CO 2 -, -CO 2 H, -CO 2 - Z +, -CO 2 R10, -SO 3 R10 or -SO 2 NR11R12, Y represents an anion , R 10 is an alkyl group of C1 to C20, a hydrogen atom contained in the alkyl group may be substituted by a halogen atom, Z + is + N (R13) 4 , Na + or K + , and R11, R12 and R13 each independently represent A hydrogen atom or a C1 to C20 alkyl group, and p represents an integer of 0 to 4. 如申請專利範圍第3項所述之著色樹脂組成物,其中所述染料更包括具有如化學式3所示的結構的化合物:[化學式3]其中R1~R4各自獨立地表示氫原子、一R8或碳數6~10的一價芳香族烴基,或者R1和R2、以及R3和R4各自一起形成包含氮原子的環,該芳香族烴基中包含的氫原子可以經鹵原子、一R8、一OH、一OR8、一SO3 -、一SO3H、一SO3 -M+、一CO2H、一CO2R8、一SO3R8或一SO2NR9R10取代;R5表示一OH、一SO3 -、一SO3H、一SO3M+、一CO2H、一CO2M+、一CO2R8、一SO3R8或一SO2NR9R10;n表示0~5的整數;在n為2以上的整數的情況下,多個R5可以相同也可以相互不同;R6和R7各自獨立地表示氫原子或碳數1~6的烷基;M+表示+N(R11)4、Na+或K+,W表示鹵原子;R8表示碳數1~20的一價飽和烴基,該飽和烴基中包含的氫原子可以經碳數6~10的芳香族烴基或鹵原子取代,該飽和烴基中包含的一CH2-可以被一S-、一O-、一CO一或一NR11-置換;R11表示氫原子、碳數1~20的一價飽和烴基或碳數7~10的芳烷基,在存在多個R11的情況下,它們的全部或一部分可以相同;R9和R10各自獨立地表示氫原子、或碳數1~20的一價飽和烴基,該飽和烴基中包含的氫原子可以經一OH或鹵原子取代,該飽和脂肪族烴基中包含的一CH2-可以被一S-、一O-、一CO-、一NH-或一NR8-置換,R9和R10可以相互鍵合而形成包含氮原子的3~10元環的雜環;鹵原子係為氟原子、氯原子、溴原子或碘原子,b表示1以上的正整數。The colored resin composition according to item 3 of the scope of patent application, wherein the dye further includes a compound having a structure as shown in Chemical Formula 3: [Chemical Formula 3] R1 to R4 each independently represent a hydrogen atom, one R8 or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms, or R1 and R2, and R3 and R4 each together form a ring containing a nitrogen atom, and the aromatic hydrocarbon group contains the hydrogen atoms may be by a halogen atom, an R8, an OH, a OR8, a SO 3 -, a SO 3 H, a SO 3 - M +, a CO 2 H, a CO 2 R8, a SO 3 R8 or a SO 2 NR9R10 substituent; R5 represents an OH, a SO 3 -, a SO 3 H, a SO 3 M +, a CO 2 H, a CO 2 M +, a CO 2 R8, a SO 3 R8 or a SO 2 NR9R10; n represents an integer of 0 to 5; when n is an integer of 2 or more, multiple R5 may be the same or different from each other; R6 and R7 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; M + represents + N (R11) 4 , Na + or K + , and W represents a halogen atom; R8 represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group can pass 6 to 10 carbon atoms. An aromatic hydrocarbon group or a halogen atom is substituted, and one CH 2 -contained in the saturated hydrocarbon group may be replaced by one S-, one O-, one CO one, or one NR11-; R11 represents a hydrogen atom and a monovalent carbon number of 1 to 20. Saturated hydrocarbon group or aralkyl group with 7-10 carbon atoms, In the case where there are multiple R11, all or part of them may be the same; R9 and R10 each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms. The hydrogen atom contained in the saturated hydrocarbon group may be OH or halogen atom substitution, one CH 2 -contained in the saturated aliphatic hydrocarbon group may be replaced by one S-, one O-, one CO-, one NH- or one NR8-, and R9 and R10 may be bonded to each other to form A 3- to 10-membered heterocyclic ring containing a nitrogen atom; the halogen atom is a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and b represents a positive integer of 1 or more. 如申請專利範圍第1項所述之著色樹脂組成物,其中所述具有如化學式1所示的結構的化合物佔所述著色樹脂組成物的1~7wt%。The colored resin composition according to item 1 of the scope of the patent application, wherein the compound having a structure as shown in Chemical Formula 1 accounts for 1 to 7 wt% of the colored resin composition. 一種彩色濾光片,由如申請專利範圍第1~5項中任一項所述之著色樹脂組成物所形成。A color filter is formed of the colored resin composition according to any one of claims 1 to 5 of the scope of patent application. 一種顯示裝置,包括如申請專利範圍第6項所述之彩色濾光片。A display device includes the color filter described in item 6 of the scope of patent application.
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