Organic encapsulation film composition and its application

An organic encapsulation film composition with cyclic (meth)acrylate and fluorine-containing (meth)acrylate addresses the limitations of existing dielectric materials by providing low dielectric constant and flexibility, suitable for low-temperature processing and enhancing the performance of optoelectronic components.

CN116041999BActive Publication Date: 2024-12-24SHANGSAI (HUANGGANG) NEW MATERIALS CO LTD
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Patent Information

Application Number
CN202211717348.3
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2022-12-29
Publication Date
2024-12-24
Estimated Expiration
2042-12-29

AI Technical Summary

Technical Problem

Existing organic dielectric materials for optoelectronic components suffer from insufficient dielectric properties, poor thermal stability, high thermal expansion coefficients, and water absorption, making them unsuitable for ultra-large-scale integrated circuits and packaging applications.

Method used

An organic encapsulation film composition comprising cyclic (meth)acrylate, fluorine-containing (meth)acrylate, and a photoinitiator, along with optional additives, is developed to provide low dielectric constant, flexibility, and improved mechanical properties through photocuring.

Benefits of technology

The composition achieves low dielectric properties, enhanced flexibility, and improved mechanical strength, suitable for low-temperature processing, addressing the limitations of existing materials and extending the service life of optoelectronic components.

✦ Generated by Eureka AI based on patent content.

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Patent Text Reader

Abstract

The present invention belongs to the field of optoelectronic material application technology, and specifically relates to an organic encapsulation film composition and its application. The organic encapsulation film composition comprises cyclic (meth) acrylate, fluorine-containing (meth) acrylate, and a photoinitiator; wherein the cyclic (meth) acrylate comprises alicyclic (meth) acrylate and heterocyclic alkane (meth) acrylate. The organic encapsulation film composition provided by the present invention has the excellent comprehensive properties of low dielectric, good flexibility, and can be prepared by photocuring.
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Description

Technical Field

[0001] The invention belongs to the field of photoelectric material application technology, and specifically relates to an organic encapsulation film composition and application thereof. Background Art

[0002] Intelligence has become one of the hot spots in the development of science and technology in the world today. From large countries to small technology companies, everyone hopes to seize the opportunity in the rapidly developing process of intelligence. Optoelectronic components such as flexible displays, chips, sensors, etc. with high performance, lightweight, miniaturization and integration are indispensable elements of intelligence. Dielectric materials play an important role in realizing the high performance, lightweight, miniaturization and integration of these optoelectronic components, such as protecting circuits, isolating insulation, buffering heat and preventing signal distortion. Therefore, the dielectric is required to have high insulation resistance, low dielectric constant, dense film layer, good elasticity, toughness and hardness, etc. The dielectric constant of dielectric materials mainly depends on the internal polarization degree of the material in the electric field. To obtain a thin film material with a low dielectric constant, the polarization degree of the material must be reduced. There are two main methods. One is to reduce the polarization ability of the molecules that make up the material, such as introducing saturated σ bonds such as CC, CH, C-Si, CF bonds, and the other is to reduce the number of polarized molecules per unit volume. Organic low-dielectric materials designed by people, such as polyimide, polyarylether, aromatic heterocyclic polymers and polyaryl hydrocarbons (SiLK), have disadvantages such as insufficient dielectric properties, poor thermal stability, low hardness, large thermal expansion coefficient and water absorption rate. In addition, organic light-emitting elements are easy to deteriorate at high temperatures, and it is difficult to apply thermosetting resin compositions. They cannot meet the requirements of ultra-large-scale integrated circuit interlayers or packaging. Therefore, the continuous innovation and performance improvement of low-temperature curing low-dielectric materials has always been a difficult and urgent problem that needs to be solved in the optoelectronic industry. Summary of the invention

[0003] The object of the present invention is to provide an organic encapsulation film composition with low dielectric constant, good flexibility and excellent comprehensive performance which can be prepared by photocuring.

[0004] The first aspect of the present invention provides an organic encapsulation film composition, comprising a cyclic (meth)acrylate, a fluorine-containing (meth)acrylate, and a photoinitiator; wherein the cyclic (meth)acrylate comprises an alicyclic (meth)acrylate and a heterocycloalkane (meth)acrylate.

[0005] The cyclic (meth)acrylate, taking it as an example, refers to: cyclic acrylate or cyclic methacrylate. It can be understood according to the commonly used expressions in the art. This is the case for other identical expressions in this patent.

[0006] Fluorine-containing (meth)acrylate can be represented by the following general formula I:

[0007]

[0008] wherein each X is independently H or F, R1 is a C1-C6 alkyl group substituted or unsubstituted with a fluorine atom, and Ar1 is a C1-C6 alkyl group substituted or unsubstituted with a hydroxyl group or a methoxy group. 15 Alkyl, hydroxyl or methoxy substituted or unsubstituted C1-C 15 Fluorinated alkyl, hydroxyl or methoxy substituted or unsubstituted C1-C 15 ether groups, hydroxyl or methoxy substituted or unsubstituted C1-C 15 One of a fluorine-containing ether group, an aromatic hydrocarbon group containing 1 to 2 benzene rings which is substituted or unsubstituted with a fluorine atom, and at least one of Ar1, R1 or X contains a fluorine atom;

[0009] m is selected from 1-6.

[0010] Preferably, m is selected from 1-2.

[0011] According to the above technical scheme, in the general formula I, The part is further represented by one of the following structural formulas:

[0012]

[0013] According to the above technical solution, Ar1 is selected from the compounds represented by the following general formula:

[0014]

[0015] Each X in each group is independently H or F.

[0016] According to the above technical solution, Ar1 is selected from the group represented by the following general formula:

[0017]

[0018]

[0019] The cyclic group in the cyclic (meth)acrylate is one of cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclopropene, cyclobutene, cyclopentene, cyclopentadiene, cyclohexene, cycloheptene, cyclooctene, and epoxy groups, or two or more of them are fused together by a common chemical bond.

[0020] According to the above technical scheme, the alicyclic hydrocarbon (meth)acrylate is cyclohexyl (meth)acrylate, adamantane (meth)acrylate, tricyclohexane (meth)acrylate, norbornane (meth)acrylate, cubane (meth)acrylate, decalin (meth)acrylate, dicyclopentene (meth)acrylate, norbornene (meth)acrylate, norbornadiene (meth)acrylate, the epoxy (meth)acrylate, epoxycyclohexyl (meth)acrylate.

[0021] According to the above technical scheme, the cyclohexyl (meth)acrylate is selected from: 2-cyclohexyl acrylate, 2-cyclohexyl methacrylate, methyl cyclohexyl acrylate, 1,4-cyclohexyl diacrylate, 1,4-cyclohexyl dimethacrylate; the adamantane (meth)acrylate is selected from: 1-adamantyl acrylate, 1-adamantyl methacrylate, 2-adamantyl acrylate, 2-adamantyl methacrylate, 2-methyl-2-adamantane alcohol acrylate, 2-methyl-2-adamantane alcohol methacrylate, 2-ethyl-2-adamantyl acrylate, 2-ethyl-2-adamantyl methacrylate, 2-isopropyl-2-adamantane alcohol acrylate, 2-isopropyl-2-adamantane methyl acrylate. esters, 5-ethyl-1,3-dimethacrylate adamantyl ester, 5-ethyl-1,3-dimethyl methacrylate adamantyl ester, 3,5-dimethyl-1-adamantyl acrylate, 3,5-dimethyl-1-adamantyl methacrylate, 3-hydroxy-1-adamantyl acrylate, 3-hydroxy-1-adamantyl acrylate, 3,5-dihydroxy-1-adamantyl acrylate, 3,5-dihydroxy-1-adamantyl methacrylate, trifluoromethylacrylate (2-methyl-2-adamantyl ester), 1,3-dimethacrylate adamantyl ester, 1,3-dimethacrylate adamantyl ester, 1,3-adamantanediol diacrylate, 5,7-dimethyl-1,3-adamantanediol diacrylate; The tricyclodecane (meth) acrylate is selected from the group consisting of dicyclopentyl acrylate, dicyclopentyl methacrylate, tricyclodecane dimethanol dimethacrylate, tricyclodecane dimethanol diacrylate, dicyclopentadiene acrylate, and dicyclopentadiene methacrylate; the norbornane (meth) acrylate is selected from the group consisting of norbornane-2-acrylate, norbornane-2-methacrylate, isobornyl acrylate, isobornyl methacrylate, 3-isobornyl cyclohexyl acrylate, 3-isobornyl cyclohexyl methacrylate, 6-hydroxy-5-methyl norbornane-2-acrylate, 6-hydroxy-5-methyl norbornane-2-methacrylate, 7,7-dimethyl norbornane-2-acrylate, 7,7- Dimethyl norbornane-2-methacrylate; the cubane (meth) acrylate is selected from: cubane acrylate, cubane methacrylate, 4-hydroxycubane acrylate, 4-hydroxycubane methacrylate, 4-propylcubane acrylate, 4-propylcubane methacrylate; the decahydronaphthalene (meth) acrylate is selected from: 1,4:5,8-dimethyldecahydronaphthalene-2-methacrylate, 2-ethyl-1,4:5,8-dimethyldecahydronaphthalene-2-methacrylate; the norbornene (meth) acrylate is selected from: the norbornene (meth) acrylate is selected from: 5-norbornene-2-methanol acrylate, 5-norbornene-2-methanol methacrylate;The epoxy (meth) acrylate is selected from the group consisting of (glycidyloxy)ethyl acrylate, (glycidyloxy)ethyl methacrylate, 4-hydroxybutyl acrylate glycidyl ether, 4-hydroxybutyl methacrylate glycidyl ether, glycidyloxy di(ethylene glycol) acrylate, glycidyloxy di(ethylene glycol) methacrylate, glycidyloxy polyethylene glycol acrylate, glycidyloxy polyethylene glycol methacrylate; the epoxy cyclohexyl (meth) acrylate is selected from the group consisting of: 3,4-epoxycyclohexyl methacrylate, 3,4-epoxycyclohexyl methyl methacrylate. ;

[0022] The photoinitiator used in the present invention can be a general photoinitiator, which can usually be used in a photocurable resin composition, for example: a benzoin photoinitiator, a ketone photoinitiator, a phosphine oxide photoinitiator, a peroxide photoinitiator, and an oxime ester photoinitiator.

[0023] According to the above technical scheme, the benzoin-based photoinitiator can include: benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, benzoin isobutyl ether, benzoin dimethyl ether, benzoin diethyl ether, etc. Examples of ketone photoinitiators include benzophenone, 4-phenylbenzophenone, p-chlorobenzophenone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, 2-hydroxy-2-methyl-1-[4-(tert-butyl)phenyl]-1-propanone, 2-hydroxy-2-methyl-1-phenylpropane-1-one, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-(4-hydroxyethoxy)phenyl-1-propanone, poly[2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propanone], bifunctional α-hydroxyketone, 4,4'-bis(diethylamino)benzophenone, 2,2-dimethoxyacetophenone, 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, and 2-isopropylthioxanthone. Examples of phosphine oxide photoinitiators include: (2,4,6-trimethylbenzoyl)diphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, (2,4,6-trimethylbenzoyl)phenylphosphine acid ethyl ester, etc.; examples of peroxy photoinitiators include: tert-butyl perbenzoate, diisopropylbenzene peroxide, dibenzoyl peroxide, etc.; examples of oxime ester photoinitiators include: 1-[4-(phenylthio)phenyl]-1,2-octanedione 2-(O-benzoyl oxime), 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethanone 1-(O-acetyl oxime), etc.

[0024] According to the above technical solution, the composition for forming the dielectric film also contains linear acrylate.

[0025] According to the above technical solution, the linear (meth)acrylate is bisphenol A type multifunctional (meth)acrylate, alkanol type multifunctional (meth)acrylate, polyester type multifunctional (meth)acrylate.

[0026] According to the above technical solution, the linear (meth)acrylate contains two (meth)acrylate functional groups at the end.

[0027] According to the above technical scheme, the linear (meth) acrylate is selected from: bisphenol A diacrylate, bisphenol A dimethacrylate, bisphenol A epoxy acrylate, bisphenol A epoxy methacrylate, bisphenol A polyoxyethylene ether diacrylate, bisphenol A polyoxyethylene ether dimethacrylate, ethylene glycol diacrylate, ethylene glycol dimethacrylate, 1,3-propylene glycol diacrylate, 1,3-propylene glycol dimethacrylate, butanediol diacrylate, butanediol dimethacrylate, diethylene glycol diacrylate, diethylene glycol diacrylate Methacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol dimethacrylate, 1,12-dodecanediol diacrylate, 1,12-dodecanediol dimethacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, polypropylene glycol diacrylate, polypropylene glycol dimethacrylate, polybutylene glycol diacrylate, polybutylene glycol dimethacrylate.

[0028] According to the above technical solution, when the organic encapsulation film composition contains linear (meth)acrylate, the content of the linear (meth)acrylate is 1-10 parts by weight.

[0029] Based on the above technical solution, the addition of linear acrylate can further adjust the viscosity and mechanical properties of the composition, thereby obtaining a photocurable composition having a high elastic modulus and excellent impact resistance.

[0030] According to the above technical scheme, functional additives are also added to the composition; the functional additives are one or more of dispersants, defoamers, surfactants, crosslinking agents, adhesion promoters, thickeners, solubilizers, leveling agents, ultraviolet absorbers, and polymerization inhibitors.

[0031] According to the above technical scheme, the dispersant is a solvent selected from one of alcohol solvents, ester solvents, ether solvents, ketone solvents or a mixture thereof. The alcohol solvents include but are not limited to: ethanol, isopropanol, propylene glycol, ethylene glycol isobutyl ether, polyethylene glycol PEG series, wherein the polyethylene glycol PEG series includes but is not limited to: PEG200, PEG300, PEG400, PEG600, PEG800, PEG1000; ester solvents include but are not limited to: ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol mono-n-butyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, Propylene glycol monopropyl ether acetate, propylene glycol monobutyl ether acetate, methoxybutyl acetate, 3-methoxybutyl acetate, methoxypentyl acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol mono-n-butyl ether acetate, dipropylene glycol monomethyl ether acetate, triethylene glycol monomethyl ether acetate, triethylene glycol monoethyl ether acetate, 3-methyl-3-methoxybutyl acetate, ethylene glycol diacetate, 1,3-butanediol diacetate, 1,6-hexanol diacetate, cyclohexanol acetate. Ether solvents include, but are not limited to, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-butyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monomethyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether; ketone solvents include, but are not limited to, acetone, methyl amyl ketone, methyl isopropyl ketone, methyl isoamyl ketone, diisopropyl ketone, diisobutyl ketone, methyl isobutyl ketone, cyclohexanone, ethyl amyl ketone, methyl butyl ketone, methyl hexyl ketone. The addition amount is 10-100 parts.

[0032] Preferably, no solvent is added to the composition.

[0033] According to the above technical solution, the surfactant can use a general surfactant, which can be generally used in a photocurable resin composition. The surfactant used in the present invention includes but is not limited to: BYK-300, BYK301, BYK302, BYK333, BYK352, BYK358N, BYK361N, etc. commercially available from BYK Chemical Company of Germany, KP341, KP310, KP321, etc. commercially available from Shin-Etsu Chemical Co., Ltd. The addition amount is 0.05-1 part.

[0034] According to the above technical solution, the defoamer can use a general defoamer, which can be generally used for photocurable resin compositions. The defoamers used in the present invention include but are not limited to: Shin-Etsu KS-66 defoamer from Shin-Etsu Chemical Co., Ltd. and BYK051, BYK052, BYK066N defoamers from BYK Additives (Shanghai) Co., Ltd. The addition amount is 0.05-1 part.

[0035] According to the above technical solution, the adhesion promoter can use a general adhesion promoter, which can be generally used in resin compositions. The adhesion promoter used in the present invention includes but is not limited to: bis[3-(triethoxysilyl)propyl]amine, 3-(isomethacryloyloxy)propyltrimethoxysilane, (3-mercaptopropyl)trimethoxysilane. The addition amount is 0.05-1 part.

[0036] According to the above technical scheme, the crosslinking agent used in the present invention can use a general crosslinking agent, and the general crosslinking agent can be generally used for photocurable resin compositions. The crosslinking agent used in the present invention is preferably a hydroxy-substituted or unsubstituted alkylene acrylate or alkylene ether acrylate containing 2-8 (meth)acrylate functional groups at the end. Specific examples include: bisphenol A diacrylate, bisphenol A dimethacrylate, bisphenol A epoxy acrylate, bisphenol A epoxy methacrylate, bisphenol A polyoxyethylene ether diacrylate, bisphenol A polyoxyethylene ether dimethacrylate, ethylene glycol diacrylate, ethylene glycol dimethacrylate, 1,3-propylene glycol diacrylate, 1,3-propylene glycol dimethacrylate, butanediol diacrylate, butanediol dimethacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate, 1, 6-hexanediol diacrylate, 1,6-hexanediol dimethacrylate, 1,12-dodecanediol diacrylate, 1,12-dodecanediol dimethacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, polypropylene glycol diacrylate, polypropylene glycol dimethacrylate, polybutylene glycol diacrylate, polybutylene glycol dimethacrylate, trimethylolpropane tri(meth)acrylate, glycerol trihydroxypropyl ether triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, di(trimethylolpropane) tetraacrylate, polydipentaerythritol pentaacrylate, polydipentaerythritol hexaacrylate. The addition amount is 1-10 parts.

[0037] The components in the composition are as follows in parts by weight: 10-40 parts by weight of cyclic (meth)acrylate, 10-40 parts by weight of fluorine-containing (meth)acrylate, and 0.01-5 parts by weight of photoinitiator.

[0038] The method for preparing the organic encapsulation film composition according to the above technical scheme comprises the following steps: 10-40 parts by weight of cyclic (meth)acrylate, 10-40 parts by weight of fluorine-containing (meth)acrylate, and 0.01-5 parts by weight of photoinitiator are put into a reaction kettle and stirred evenly at 20°C-60°C, and then one or more other functional additives are added to the reaction kettle as needed and stirred at 20°C-60°C for 2-6 hours to form a uniform and transparent solution, so as to prepare the organic encapsulation film composition.

[0039] The organic encapsulation film composition is coated by coating, spraying, spin coating, injection, doctor blade, brush coating, nano-imprinting, inkjet printing, screen printing or pad printing, and then cured by ultraviolet light to form an organic encapsulation film.

[0040] Another aspect of the present invention provides an application of the organic encapsulation film composition, wherein the organic encapsulation film composition is applied to display devices, integrated circuits, capacitors, wires, cables, and antennas.

[0041] The present invention provides an organic encapsulation film composition, which is mainly composed of organic substances such as fluorine-containing acrylic resin and cyclic acrylic resin, and avoids the disadvantages of the encapsulation film composition material formed by organic-inorganic hybrid materials, such as uneven quality of the encapsulation film and poor flexibility, etc., due to poor dispersibility and compatibility. The intrinsic low polarizability CF bond in the fluorine-containing acrylic resin cooperates with the microporous structure of the cyclic acrylic resin, so that the low dielectric properties of the material can meet the requirements of the encapsulation film material. At the same time, since the fluorocarbon chain is more rigid than the hydrocarbon chain, the conformation angle tension and P of the ring structure in the introduced cyclic (meth) acrylate are improved. Itzer tension and cross-ring tension enable the material to undergo rotational isomerization when subjected to stress, thereby converting kinetic energy into potential energy for release, eliminating internal stress, and complementing the fluorine-containing resin. The flexibility of the film composition material is improved, the cracking and warping deformation of the film material are solved, and the service life is extended. The viscosity of the material can be adjusted to below 25cps without the need for solvents, thereby avoiding the degradation of the flatness of the film surface due to solvent volatilization during processing or the influence of incomplete solvent volatilization on the life of the device. The material can also be prepared by low-temperature processes such as coating, spraying, spin coating, injection, scraping, brushing, nanoimprinting, inkjet printing, screen printing or pad printing (if it is greater than 30cps, thermal processing is required, and it is difficult to process if it is greater than 35cps). The material is an organic encapsulation film composition with excellent comprehensive performance, low dielectric, good flexibility, and suitable for low-temperature processing technology. It has excellent application prospects in display devices, integrated circuits, capacitors, wires, cables, and antennas. DETAILED DESCRIPTION

[0042] The principles and features of the present invention are described below. The examples given are only used to explain the present invention and are not used to limit the scope of the present invention.

[0043] Example 1

[0044] 15 parts by weight of 3-hydroxy-1-adamantyl methacrylate, 15 parts by weight of cyclohexyl acrylate, 37.5 parts by weight of 2-(perfluorooctyl)ethyl methacrylate and 5 parts by weight of polymerized [2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]acetone] are put into a reaction kettle and stirred evenly at 60° C., then 7.5 parts by weight of polyethylene glycol diacrylate and 0.5 parts by weight of BYK358N are added to the reaction kettle successively and stirred at 25° C. for 2 hours to form a uniform and transparent solution, thereby preparing the organic encapsulation film composition.

[0045] Example 2

[0046] 15 parts by weight of 3-hydroxy-1-adamantyl methacrylate, 15 parts by weight of 3-isobornyl cyclohexyl acrylate, 37.5 parts by weight of 2-(perfluorooctyl)ethyl methacrylate and 5 parts by weight of polymerized [2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]acetone] are put into a reaction kettle and stirred evenly at 60° C., then 7.5 parts by weight of polyethylene glycol diacrylate and 0.5 parts by weight of BYK358N are added to the reaction kettle successively and stirred at 25° C. for 2 hours to form a uniform and transparent solution, thereby preparing the organic encapsulation film composition.

[0047] Example 3

[0048] 15 parts by weight of 3-isobornylcyclohexyl acrylate, 37.5 parts by weight of 2-(perfluorooctyl)ethyl methacrylate and 5 parts by weight of polymerized [2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propanone] are put into a reaction kettle and stirred evenly at 60° C., then 7.5 parts by weight of polyethylene glycol diacrylate and 0.5 parts by weight of BYK358N are added to the reaction kettle successively and stirred at 25° C. for 2 hours to form a uniform and transparent solution, thereby preparing the organic encapsulation film composition.

[0049] Example 4

[0050] 10 parts by weight of dicyclopentyl methacrylate, 30 parts by weight of glycidyl ether oxypolyethylene glycol acrylate, 30 parts by weight of hexafluorobisphenol A diacrylate and 4 parts by weight of dibenzoyl peroxide are put into a reaction kettle and stirred evenly at 60° C., then 0.05 parts by weight of KP341 are added to the reaction kettle and stirred at 25° C. for 2 hours to form a uniform and transparent solution, thereby preparing the organic encapsulation film composition.

[0051] Example 5

[0052] 28 parts by weight of 4-hydroxybutyl acrylate glycidyl ether, 40 parts by weight of 2-(perfluorobutyl)ethyl methacrylate and 2.5 parts by weight of ethyl 2,4,6-trimethylbenzoylphenylphosphonate were put into a reaction kettle and stirred evenly at 60° C., then 0.1 parts by weight of BYK-333 was added to the reaction kettle and stirred at 25° C. for 2 hours to form a uniform and transparent solution, thereby preparing the organic encapsulation film composition.

[0053] Example 6

[0054] 28 parts by weight of 4-hydroxybutyl acrylate glycidyl ether, 40 parts by weight of 3,3,4,4,5,6,6,6-octafluoro-5-trifluoromethylhexyl maleate and 2.5 parts by weight of ethyl 2,4,6-trimethylbenzoylphenylphosphonate were put into a reaction kettle and stirred evenly at 60° C., then 0.1 parts by weight of BYK-333 was added to the reaction kettle and stirred at 25° C. for 2 hours to form a uniform and transparent solution, thereby preparing the organic encapsulation film composition.

[0055] Example 7

[0056] 40 parts by weight of isobornyl acrylate, 22.5 parts by weight of perfluorodiethylene glycol diacrylate and 2 parts by weight of 4,4'-bis(diethylamino)benzophenone are put into a reaction kettle and stirred evenly at 60°C. Then, 7.5 parts by weight of bisphenol A epoxy methacrylate and 0.05 parts by weight of BYK-UV3570 are added to the reaction kettle successively and stirred at 25°C for 2 hours to form a uniform and transparent solution, thereby preparing the organic encapsulation film composition.

[0057] Example 8

[0058] 8.5 parts by weight of dicyclopentadiene methacrylate, 17.5 parts by weight of norbornane-2-acrylate, 40 parts by weight of 2,2,3,3,4,4-hexafluoropentane dimethacrylate and 5 parts by weight of bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide were put into a reaction kettle and stirred evenly at 60° C., then 0.1 parts by weight of KP341 was added to the reaction kettle and stirred at 25° C. for 2 hours to form a uniform and transparent solution, thereby preparing the organic encapsulation film composition.

[0059] Example 9

[0060] 10 parts by weight of cubane methacrylate, 30 parts by weight of cyclohexyl acrylate, 32.5 parts by weight of perfluoropropane-1,3-diylbis(3,3-difluoro-2-methylacrylate) and 4 parts by weight of 1-[4-(phenylthio)phenyl]-1,2-octanedione 2-(O-benzoyloxime) are put into a reaction kettle and stirred evenly at 60° C., then 5 parts by weight of bisphenol A epoxy methacrylate, 0.05 parts by weight of 3-(isomethacryloyloxy)propyltrimethoxysilane and 0.05 parts by weight of BYK301 are added to the reaction kettle successively, and the mixture is stirred at 25° C. for 2 hours to form a uniform and transparent solution, thereby preparing the organic encapsulation film composition.

[0061] Example 10

[0062] 10 parts by weight of cubane methacrylate, 30 parts by weight of 3-isobornylcyclohexyl acrylate, 32.5 parts by weight of perfluoropropane-1,3-diylbis(3,3-difluoro-2-methylacrylate) and 4 parts by weight of 1-[4-(phenylthio)phenyl]-1,2-octanedione 2-(O-benzoyloxime) are put into a reaction kettle and stirred evenly at 60° C., then 5 parts by weight of bisphenol A epoxy methacrylate, 0.05 parts by weight of 3-(isomethacryloyloxy)propyltrimethoxysilane and 0.05 parts by weight of BYK301 are added to the reaction kettle successively, and the mixture is stirred at 25° C. for 2 hours to form a uniform and transparent solution, thereby preparing the organic encapsulation film composition.

[0063] Embodiment 11

[0064] 30 parts by weight of cyclohexyl acrylate, 32.5 parts by weight of perfluoropropane-1,3-diylbis(3,3-difluoro-2-methylacrylate) and 4 parts by weight of 1-[4-(phenylthio)phenyl]-1,2-octanedione 2-(O-benzoyloxime) are put into a reaction kettle and stirred evenly at 60° C., then 5 parts by weight of bisphenol A epoxy methacrylate, 0.05 parts by weight of 3-(isomethacryloyloxy)propyltrimethoxysilane and 0.05 parts by weight of BYK301 are successively added into the reaction kettle and stirred at 25° C. for 2 hours to form a uniform and transparent solution, thereby preparing the organic encapsulation film composition.

[0065] Example 12

[0066] 30 parts by weight of cyclohexyl acrylate, 32.5 parts by weight of perfluoropropane dimethacrylate) and 4 parts by weight of 1-[4-(phenylthio)phenyl]-1,2-octanedione 2-(O-benzoyl oxime) are put into a reaction kettle and stirred evenly at 60° C., then 5 parts by weight of bisphenol A epoxy methacrylate, 0.05 parts by weight of 3-(isomethacryloyloxy)propyltrimethoxysilane and 0.05 parts by weight of BYK301 are successively added into the reaction kettle and stirred at 25° C. for 2 hours to form a uniform and transparent solution, thereby preparing the organic encapsulation film composition.

[0067] Comparative Example 1

[0068] 28 parts by weight of butanediol diacrylate, 40 parts by weight of 2-(perfluorobutyl)ethyl methacrylate and 2.5 parts by weight of ethyl 2,4,6-trimethylbenzoylphenylphosphonate were put into a reaction kettle and stirred evenly at 60° C., then 0.1 parts by weight of BYK-333 was added to the reaction kettle and stirred at 25° C. for 2 hours to form a uniform and transparent solution, thereby preparing the organic encapsulation film composition.

[0069] For the organic encapsulation film compositions prepared in Examples 1 to 12 and Comparative Example 1, the viscosity at 25° C. was tested using a rotary viscometer of model LV-SSR, the surface tension at 25° C. was tested using an automatic surface tension meter of model BZY-101, the dielectric constant was tested using an LCR meter and an impedance analyzer, and the elongation at break of a film having a thickness of 5 μm formed after curing by irradiating 395 nm ultraviolet light at 2000 mJ / cm was tested using an AGS-X universal testing machine. The test results are described in the following table.

[0070]

[0071]

[0072] It can be seen from the above table that the intrinsic low polarizability CF bond in the fluorine-containing acrylic resin cooperates with the microporous structure of the cyclic acrylic resin, so that the material has lower low dielectric properties. At the same time, since the fluorocarbon chain is more rigid than the hydrocarbon chain, the cyclic structure in the cyclic (meth) acrylate eliminates internal stress through rotational isomerization, complements the fluorine-containing resin, and improves the flexibility of the film composition material. The elongation at break of Examples 1 to 12 is significantly improved compared to the conventional acrylate without a cyclic structure in Comparative Example 1. In general, the encapsulation film composition material of the present invention provides excellent viscosity, dielectric properties and flexibility, is suitable for low-temperature processing technology, and has excellent comprehensive performance.

[0073] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims

1. An organic encapsulation film composition, characterized in that: Include: Cyclic (meth)acrylates; Fluorinated (meth)acrylates; Photoinitiator; The cyclic (meth)acrylate is selected from cyclohexyl (meth)acrylate, tricyclodecane (meth)acrylate, norbornane (meth)acrylate, cubane (meth)acrylate, decalin (meth)acrylate, dicyclopentene (meth)acrylate, norbornene (meth)acrylate, and epoxy (meth)acrylate; The fluorine-containing (meth)acrylate is represented by the following general formula I: wherein each X is independently H or F, R1 is a C1-C6 alkyl group substituted or unsubstituted with a fluorine atom, and Ar1 is a C1-C6 alkyl group substituted or unsubstituted with a hydroxyl group or a methoxy group. 15 Alkyl, hydroxyl or methoxy substituted or unsubstituted C1-C 15 Fluorinated alkyl, hydroxyl or methoxy substituted or unsubstituted C1-C 15 ether groups, hydroxyl or methoxy substituted or unsubstituted C1-C 15 One of a fluorine-containing ether group, an aromatic hydrocarbon group containing 1 to 2 benzene rings substituted or unsubstituted with a fluorine atom, and at least one of Ar1, R1 or X contains a fluorine atom; m is selected from 1 to 6; The components in the organic encapsulation film composition are calculated in parts by weight as follows: 10-40 parts by weight of cyclic (meth)acrylate; 10-40 parts by weight of fluorine-containing (meth)acrylate; and 0.01-5 parts by weight of photoinitiator.

2. The organic encapsulation film composition according to claim 1, characterized in that: In the general formula I The part is further represented by one of the following structural formulas:

3. The organic encapsulation film composition according to claim 1, characterized in that: The Ar1 is selected from the compounds represented by the following general formula: Each X in each group is independently H or F.

4. The organic encapsulation film composition according to claim 1, characterized in that: Functional additives are also added to the composition; the functional additives are one or more of dispersants, defoamers, surfactants, crosslinking agents, adhesion promoters, thickeners, solubilizers, leveling agents, ultraviolet absorbers or polymerization inhibitors.

5. The organic encapsulation film composition according to claim 1, characterized in that : The epoxy (meth) acrylate is epoxy cyclohexyl (meth) acrylate.

6. The organic encapsulation film composition according to claim 1, characterized in that: The norbornene (meth)acrylate is norbornadiene (meth)acrylate.

7. The organic encapsulation film composition according to claim 1, characterized in that: The organic encapsulation film composition is formed by coating by spraying, spin coating, brush coating, injection, doctor blade, nano-imprinting, inkjet printing, screen printing or pad printing and then cured by ultraviolet light.

8. A use of the organic encapsulation film composition according to any one of claims 1 to 7, characterized in that: The organic encapsulation film composition is used for preparing a display device, an integrated circuit, a capacitor, a wire or an antenna.

Citation Information

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