KR-20260062257-A - Low dielectric coating composition containing ultraviolet blocking monomers

KR20260062257AKR 20260062257 AKR20260062257 AKR 20260062257AKR-20260062257-A

Abstract

The present invention relates to a low dielectric coating liquid composition comprising a difunctional acrylic compound (B) having low dielectric properties, comprising an ultraviolet blocking monomer (A). More specifically, the invention relates to an ultraviolet blocking low dielectric coating liquid composition having the advantages of excellent cutting ability against ultraviolet and blue light, having a low dielectric constant, having strong resistance to plasma, and exhibiting a low curing shrinkage rate.

Inventors

강지승
최혜라
남은정
허영태
정동섭
허재호
문봉석
홍원기
하민수
이규성
박노길
이현우
변우근
김영은

Assignees

삼성디스플레이 주식회사
주식회사 트리엘

Dates

Publication Date: 20260507
Application Date: 20241028

Claims (18)

A low dielectric coating liquid composition comprising: a UV blocking monomer (A) represented by the following chemical formula 1; a difunctional acrylic compound (B) represented by the following chemical formula 2; and a monofunctional acrylic compound (C) represented by the following chemical formula 3 that is polymerizable with the difunctional acrylic compound (B). [Chemical Formula 1] In the above chemical formula 1, The substituent R1 is any one selected from hydrogen, deuterium, halogen, nitro group, and cyano group, and The substituent R2 is any one selected from a halogen, a nitro group, a cyano group, a hydroxyl group, a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted C1-C8 alkoxy group, a substituted or unsubstituted C1-C8 hydroxyalkyl group, a substituted or unsubstituted C1-C4 monosubstituted amino group, a substituted or unsubstituted C1-C4 disubstituted amino group, a substituted or unsubstituted C1-C3 carboxyalkyl group, and a substituted or unsubstituted C1-C12 perfluoroalkyl group. The substituent R3 is any one selected from hydrogen, deuterium, a substituted or unsubstituted C1-C24 alkyl group, a substituted or unsubstituted C1-C24 alkoxy group, a substituted or unsubstituted C2-C24 alkenyl group, a substituted or unsubstituted C2-C24 alkynyl group, a substituted or unsubstituted C6-C15 aryl group, a substituted or unsubstituted C7-C24 arylalkyl group, a substituted or unsubstituted C7-C24 alkylaryl group, and a substituted or unsubstituted C1-C12 carboxyalkyl group. The substituent R4 is any one selected from hydrogen, deuterium, and substituted or unsubstituted C1-C10 alkyl groups, and The above linker L1 is any one selected from a single bond, a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C1-C20 halogenated alkylene group, a substituted or unsubstituted C1-C20 alkylene ether group, a substituted or unsubstituted C2-C20 alkenylene group, a substituted or unsubstituted C2-C20 alkynylene group, a substituted or unsubstituted C1-C20 heteroalkylene group, a substituted or unsubstituted C6-C15 arylene group, a substituted or unsubstituted C7-C24 arylalkylene group, and a substituted or unsubstituted C7-C24 alkylarylene group. Connector X is any one selected from oxygen (O), sulfur (S), and NR, and The above R is any one selected from hydrogen, deuterium, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 halogenated alkyl group, a substituted or unsubstituted C7-C20 arylalkyl group, and a C4-C20 heteroaryl group comprising 1 to 3 heteroatoms selected from O, N, and S as heteroatoms that are substituted or unsubstituted. [Chemical Formula 2] In the above chemical formula 2, The above substituents R5 and R6 are each the same or different and independently selected from hydrogen, deuterium, and substituted or unsubstituted C1-C10 alkyl groups, and The above substituent Y1 is any one selected from hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 alkyl halide group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted C1-C10 heteroalkyl group, and a substituted or unsubstituted C1-C10 alkoxy group. The above substituent Y2 is any one selected from hydrogen, deuterium, a substituted or unsubstituted C3-C30 alkyl group, a substituted or unsubstituted C3-C30 alkyl halide group, a substituted or unsubstituted C4-C30 alkenyl group, a substituted or unsubstituted C4-C30 alkynyl group, a substituted or unsubstituted C3-C30 heteroalkyl group, and a substituted or unsubstituted C3-C30 alkoxy group, and The above linker L is any one selected from a single bond, a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C1-C30 halogenated alkylene group, a substituted or unsubstituted C2-C30 alkenylene group, a substituted or unsubstituted C2-C30 alkynylene group, a substituted or unsubstituted C1-C30 heteroalkylene group, and -OL'O-, Here, L' is any one selected from a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C1-C30 halogenated alkylene group, a substituted or unsubstituted C6-C18 arylene group, a substituted or unsubstituted C2-C30 alkenylene group, a substituted or unsubstituted C2-C30 alkynylene group, and a substituted or unsubstituted C1-C30 heteroalkylene group. l and n are each the same or different, and independently 0 or 1, and m is 1 or 2, and when m is 2, each L is the same or different from each other, and When all of the above m linkers L are single bonds and l is 0, n is 1 and also Y 2 is a substituent that is not hydrogen or deuterium, and The above connectors X1 and X2 are each identical or different and independently selected from oxygen (O), sulfur (S), and N-R', and The above R' is identical to the substituent R in the above chemical formula 1, and [Chemical Formula 3] In the above [Chemical Formula 3], Each of the above substituents R7 is selected from hydrogen, deuterium, and substituted or unsubstituted C1-C10 alkyl groups, and The above substituent R8 is any one substituent selected from a substituted or unsubstituted C3-C40 alkyl group, a substituted or unsubstituted C3-C40 halogenated alkyl group, a substituted or unsubstituted C3-C40 alkenyl group, a substituted or unsubstituted C3-C40 alkynyl group, an arylalkyl group comprising only one substituted or unsubstituted C8-C40 benzene ring, and an alkylaryl group comprising only one substituted or unsubstituted C8-40 benzene ring. The above connector X 3 is any one selected from oxygen (O), sulfur (S), and NR, and The above R” is identical to the substituent R in the above chemical formula 1, and The term "substituted" in "substituted or unsubstituted" in Formulas 1 to 3 above refers to deuterium, cyano group, halogen group, hydroxyl group, nitro group, C1 - C24 alkyl group, C1 - C24 halogenated alkyl group, C2 - C24 alkenyl group, C2 - C24 alkynyl group, C1-24 heteroalkyl group, C6-C24 aryl group , C7 - C24 arylalkyl group, C2 - C24 heteroaryl group, C2- C24 heteroarylalkyl group, C1-C24 alkoxy group, C1 - C24 alkylthionyl group, C1 - C24 alkylamino group, C6 - C24 It means being substituted with one or more substituents selected from the group consisting of arylamino groups, C1 - C24 heteroarylamino groups, C1 - C24 alkylsilyl groups, C6 - C24 arylsilyl groups, C6 - C24 aryloxy groups, and C6 - C24 arylthionyl groups.
In paragraph 1, A low dielectric coating liquid composition characterized in that the above substituents R 4 to R 7 are each the same or different and are independently selected from hydrogen, deuterium, and C1-C5 unsubstituted alkyl groups.
In paragraph 1, A low dielectric coating liquid composition characterized in that the substituent L1 in the above chemical formula 1 is selected from any one of a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C1-C20 halogenated alkylene group, a substituted or unsubstituted C1-C20 alkylene ether group, and a substituted or unsubstituted C1-C20 heteroalkylene group.
In paragraph 1, A low dielectric coating liquid composition characterized in that the substituent Y1 in the above chemical formula 2 is selected from hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 alkyl halide group, and a substituted or unsubstituted C1-C10 alkoxy group.
In paragraph 1, A low dielectric coating liquid composition characterized in that the substituent Y2 in the above chemical formula 2 is selected from hydrogen, deuterium, a substituted or unsubstituted C3-C30 alkyl group, a substituted or unsubstituted C3-C30 alkyl halide group, and a substituted or unsubstituted C3-C30 alkoxy group.
In paragraph 1, A low dielectric coating liquid composition characterized in that the linker L in the above chemical formula 2 is selected from a single bond, a substituted or unsubstituted C1-C30 alkylene group.
In paragraph 1, A low dielectric coating liquid composition characterized in that the substituent R8 in the above chemical formula 3 is selected from any one of a substituted or unsubstituted C3-C40 alkyl group, a substituted or unsubstituted C3-C40 halogenated alkyl group, a substituted or unsubstituted C9-C40 arylalkyl group containing only one benzene ring, and a substituted or unsubstituted C9-C40 alkylaryl group containing only one benzene ring.
In paragraph 1, A low dielectric coating liquid composition characterized in that the above substituents X, X1 to X3 are each oxygen (O) or sulfur (S).
In paragraph 1, A low dielectric coating liquid composition characterized in that the UV blocking monomer represented by the above chemical formula 1 is any one selected from <Compound 1> to <Compound 60> below. <Compound 1><Compound2><Compound3> <Compound 4><Compound5><Compound6> <Compound 7><Compound8><Compound9> <Compound 10><Compound11><Compound12> <Compound 13><Compound14><Compound15> <Compound 16><Compound17><Compound18> <Compound 19><Compound20><Compound21> <Compound 22><Compound23><Compound24> <Compound 25><Compound26><Compound27> <Compound 28><Compound29><Compound30> <Compound 31><Compound32><Compound33> <Compound 34><Compound35><Compound36> <Compound 37><Compound38><Compound39> <Compound 40><Compound41><Compound42> <Compound 43><Compound44><Compound45> <Compound 46><Compound47><Compound48> <Compound 49><Compound50><Compound51> <Compound 52><Compound53><Compound54> <Compound 55><Compound56><Compound57> <Compound 58><Compound59><Compound60>
In paragraph 1, The difunctional acrylic compound (B) represented by the above chemical formula 2 comprises two groups in an alkanediol having a straight-chain methylene structure, such as 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, 1,12-dodecanediol di(meth)acrylate, 1,14-tetradecanediol di(meth)acrylate, 1,14-tetradecanediol di(meth)acrylate, 1,16-hexadecanediol di(meth)acrylate, dodecane-1,2-di(meth)acrylate, tetradecane-1,2-di(meth)acrylate, and polytetramethyleneglycol di(meth)acrylate. Structures substituted with (meth)acrylic groups, polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, etc., structures in which two (meth)acrylic groups are substituted on polyethylene glycol or polypropylene glycol, tricyclodecanedimethanol diacrylate, adamantan-1,2-dinylda(meth)acrylate, adamantan-1,3-diol di(meth)acrylate, adamantan-1,3-dimethanol di(meth)acrylate, adamantan-1,3-diethanol di(meth)acrylate, 5,7-dimethyladamantan-1,3-diol di(meth)acrylate, 5,7-Dimethyladamantan-1,3-DimethanolDi(Meta)Acrylate, A low dielectric coating liquid composition characterized by using one to five compounds selected from 5,7-dimethyladamantan-1,3-diethanol di(meth)acrylate alone or in combination.
In paragraph 1, The monofunctional acrylic compound (C) represented by the above chemical formula 3 is propyl(meth)acrylate, butyl(meth)acrylate, hexyl(meth)acrylate, octyl(meth)acrylate, cyclohexyl(meth)acrylate, decyl(meth)acrylate, lauryl(meth)acrylate, dodecyl(meth)acrylate, hexadecyl(meth)acrylate, octadecyl(meth)acrylate, icosyl(meth)acrylate, butycosyl(meth)acrylate, isobornyl(meth)acrylate, adamantyl(meth)acrylate, benzyl(meth)acrylate, phenoxybenzyl(meth)acrylate, 2-methoxyethyl(meth)acrylate, 2-ethoxyethyl(meth)acrylate, Characterized by using one to five compounds selected from 2-decyltetradecyl (meth)acrylate, 2-dodecylhexadecyl (meth)acrylate, dicyclofentanyl (meth)acrylate, dicyclofentenyl (meth)acrylate, dicyclofentenyloxyethyl (meth)acrylate, cyclohexyl (meth)acrylate, cyclohexanedimethanol mono(meth)acrylate, 5-methyl-5-dicyclofentanyl (meth)acrylate, 5-ethyl-5-dicyclofentanyl (meth)acrylate, 5-isopropyl-5-dicyclofentanyl (meth)acrylate, 4-dicyclofentanyl (meth)acrylate, and 2-(dicyclopentan-4-nyl)ethyl (meth)acrylate, either alone or in a mixture. Low dielectric coating liquid composition.
In paragraph 1, A low dielectric coating liquid composition characterized in that the above-mentioned UV blocking monomer (A) is in the range of 1 to 20 parts by weight based on 100 parts by weight of the total amount of the composition excluding the UV blocking monomer (A) in the total composition.
In paragraph 1, The above coating liquid composition is characterized by additionally including a polymerization initiator (D).
In Paragraph 13, A low dielectric coating composition characterized by comprising, based on a total content of 100% by weight of the total composition, 10 to 70% by weight of an acrylic compound (B) represented by Chemical Formula 2; 10 to 80% by weight of a monofunctional acrylic compound (C) capable of polymerizing with the acrylic compound (B); and 0.1 to 20% by weight of a polymerization initiator (D).
In paragraph 1, The above coating solution composition further comprises an organic solvent, wherein A low dielectric coating liquid composition characterized by comprising 1 to 300 parts by weight of the organic solvent, based on 100 parts by weight of the total amount of the composition excluding the organic solvent.
An organic coating film characterized by being manufactured by heat curing or photocuring a coating liquid composition described in any one of claims 1 to 15.
In Paragraph 16, The above organic coating film is characterized by additionally including one or more of an organic layer or an inorganic layer.
In Paragraph 16, The above organic coating film is characterized by being used in any one selected from organic light-emitting diodes, electrochromic devices, photochromic devices, solar cells, lighting devices, integrated circuits, LCD devices, light-emitting diodes, and encapsulating materials.

Description

Low dielectric coating composition containing ultraviolet blocking monomers The present invention relates to a low dielectric coating liquid composition comprising an ultraviolet blocking monomer (A), and more specifically, to a low dielectric coating liquid composition capable of realizing excellent cutting ability of ultraviolet and blue light and a low dielectric constant of an organic coating film formed by a sealing coating liquid composition used for applications such as semiconductors, electronic devices, and displays. As a sealing coating composition used for applications such as semiconductors, electronic devices, and displays, polymers of acrylates or methacrylates may be used. These serve as useful monomer components that provide polymers with various excellent performance characteristics when polymerized alone or copolymerized with other monomers. Polymers prepared using these components generally exhibit excellent weather resistance and transparency. Furthermore, since polymers with diverse performance characteristics can be produced depending on the type of ester substituent, they have high potential for application, particularly as coating compositions for sealing or display applications. For example, acrylates or methacrylates in which bulky alicyclic substituents are introduced as ester substituents have low chemical reactivity and can be copolymerized with existing polymer monomers, so there is high industry interest in their commercial production. As prior art regarding such coating compositions for sealing or display purposes, Korean Published Patent Application No. 10-2016-0030077 (March 16, 2016) describes a resin composition for sealing organic EL devices and a cured product thereof, Korean Published Patent Application No. 10-2019-0065896 (June 26, 2019) describes a composition for encapsulating organic light-emitting diodes and an organic light-emitting diode display device manufactured therefrom, and Korean Published Patent Application No. 10-2016-0053751 (May 13, 2016) presents a composition for a display sealing material, an organic protective layer including the same, and a display device including the same. However, despite the prior art including the aforementioned prior art, there is a need for a coating liquid composition suitable for a process of forming a resin layer on a continuously moving substrate as a coating composition for sealing or display applications, which has a low dielectric constant and excellent adhesion, and there is a continuous need for the development of a novel coating liquid composition having these characteristics. Meanwhile, adverse effects caused by the eyes being exposed to ultraviolet rays or visible light near ultraviolet rays have been a concern for some time. In particular, light in the blue region (380 to 500 nm) (blue light) has high energy and can cause damage to the user's retina, etc. To prevent damage caused by the blue light (blue light hazard), it is desirable to cut out blue light with a relatively short wavelength of 380 to 405 nm among visible light. However, conventional methods for cutting this use a method of lowering the brightness of blue light through a driving program during the operation of the finished product to reduce damage caused by ultraviolet rays. In this case, the overall brightness is lowered and the color quality may decrease. In addition, ultraviolet or ultraviolet-side visible light components emitted from the display pixels can cause damage to surrounding elements if emitted for a long time, so it is necessary to block these ultraviolet components. Therefore, there is a need to develop a display device capable of blocking ultraviolet components emitted from display pixels or blue light components in the short-wavelength region of visible light without affecting overall brightness. Unless otherwise specifically defined in this invention, technical terms used in this invention shall be interpreted in the sense generally understood by those skilled in the art to which this invention pertains, and shall not be interpreted in an overly broad or overly narrow sense. In describing the principles of a preferred embodiment of the present invention in detail, if it is determined that a specific description of related known functions or configurations could unnecessarily obscure the essence of the present invention, such detailed description is omitted. Specific examples of the present application are to be described in more detail. However, the contents described in the present application are provided to convey the spirit of the present application and are not limited thereto. The low dielectric coating liquid composition according to the present invention is characterized by comprising a UV blocking monomer (A) represented by the following chemical formula 1, a difunctional acrylic compound (A) represented by the following chemical formula 2, a monofunctional acrylic compound (C) represented by the following chemical fo