CN111808559A - Photocuring adhesive layer composition, adhesive and adhesive tape - Google Patents

Photocuring adhesive layer composition, adhesive and adhesive tape Download PDF

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Publication number
CN111808559A
CN111808559A CN202010714952.5A CN202010714952A CN111808559A CN 111808559 A CN111808559 A CN 111808559A CN 202010714952 A CN202010714952 A CN 202010714952A CN 111808559 A CN111808559 A CN 111808559A
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molecular weight
acrylic monomer
acrylic
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张程
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Shanghai Guke Adhesive Tape Technology Co ltd
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Shanghai Guke Adhesive Tape Technology Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J135/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J135/02—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/22—Plastics; Metallised plastics
    • C09J7/25—Plastics; Metallised plastics based on macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C09J7/255—Polyesters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
    • H01L21/304—Mechanical treatment, e.g. grinding, polishing, cutting
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2467/00—Presence of polyester
    • C09J2467/006—Presence of polyester in the substrate

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Physics & Mathematics (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
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  • Manufacturing & Machinery (AREA)
  • Physics & Mathematics (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

The invention relates to the relevant field of adhesives, and particularly provides a photocuring adhesive layer composition, an adhesive and an adhesive tape, wherein the photocuring adhesive layer composition comprises the following raw materials: (a) an acrylic prepolymer; (b) a polymerization initiator which accounts for 0.05 to 1.5 wt% of the acrylic prepolymer; preferably 0.1 to 0.9 wt%; further preferably 0.3 to 0.6 wt%; wherein the acrylic prepolymer is formed by (c) acrylic monomer without active group with weight average molecular weight of 200-800 g/mol, (d) acrylic monomer with active group with weight average molecular weight of 150-650 g/mol and (e) diisocyanate; and the active group comprises any one or more of amino, hydroxyl, carboxyl, amido, phenolic hydroxyl and maleic anhydride. The invention provides a UV-curable adhesive layer composition, which has better viscosity before UV irradiation and avoids splashing in the wafer cutting process; meanwhile, the wafer is easy to peel off after UV irradiation, the picking performance is good, and the phenomenon of wafer pollution or residual glue can not occur.

Description

Photocuring adhesive layer composition, adhesive and adhesive tape
Technical Field
The invention relates to the relevant field of adhesives, and particularly provides a photocuring adhesive layer composition, an adhesive and an adhesive tape.
Background
In recent years, semiconductor components have been rapidly developed, electronic devices tend to be small, light, high in performance and multifunctional, and the preparation of electronic devices depends on the size and refinement of chips to a great extent.
The preparation process of the chip involves the processes of cutting, picking and re-pasting, but in the process, the chip is firstly pasted and fixed through an adhesive tape and needs a certain adhesive force, otherwise, the chip is easy to splash in the cutting process, so that the chip is damaged; in addition, after cutting, the adhesion needs to be reduced after UV irradiation, the mechanical arm is used for high-precision positioning and grabbing the chip, otherwise, the adhesion force is still large after UV irradiation possibly occurs, the mechanical arm cannot achieve good picking, the chip can be damaged in the same way, the surface of the chip can be provided with adhesive residue, and the quality of the chip is affected.
Disclosure of Invention
The technical problem to be solved by the invention is as follows: the invention provides a UV-curable adhesive layer composition, which has better viscosity before UV irradiation and avoids splashing in the wafer cutting process; meanwhile, the wafer is easy to peel off after UV irradiation, the picking performance is good, and the phenomenon of wafer pollution or residual glue can not occur.
The technical scheme adopted by the invention is as follows:
the invention provides a photocuring glue layer composition in a first aspect, which comprises the following raw materials:
(a) an acrylic prepolymer;
(b) a polymerization initiator which accounts for 0.05 to 1.5 wt% of the acrylic prepolymer; preferably 0.1 to 0.9 wt%; further preferably 0.3 to 0.6 wt%;
wherein the acrylic prepolymer is formed by raw materials of (c) acrylic monomer without active group with the weight-average molecular weight of 200-800 g/mol, (d) acrylic monomer with active group with the weight-average molecular weight of 150-650 g/mol and (e) diisocyanate; and the active group comprises any one or more of amino, hydroxyl, carboxyl, amido, phenolic hydroxyl and maleic anhydride.
The invention adopts acrylic monomers without active groups and with the weight-average molecular weight of 200-800 g/mol, acrylic monomers with active groups and with the weight-average molecular weight of 150-650 g/mol and diisocyanate to form acrylic prepolymer, namely, the diisocyanate and the acrylic monomers with active groups are utilized to form oligomer with a three-dimensional network structure, so as to be further used for coating the glue line composition; in practical use, in order to control the action of the adhesive layer composition with a base material in the using process, avoid delamination, control the cohesive force of the adhesive layer and the proper adhesive force with a chip or a wafer, and avoid the problems of splashing or adhesive residue, the weight ratio of (c), (d) and (e) needs to be controlled to be 1: (0.55-0.75): (0.45-0.56).
The "weight average molecular weight" in the present invention is a molecular weight obtained by averaging the statistical average molecular weight by mass per unit weight, and is measured by Gel Permeation Chromatography (GPC).
Preferably, the (c) acrylic monomer having a weight average molecular weight of 200 to 800g/mol and not containing an active group in the present invention includes (c1) an acrylic monomer having a number of double bonds as a monofunctional group having a weight average molecular weight of 200 to 350g/mol, (c2) an acrylic monomer having a number of double bonds as a bifunctional group having a weight average molecular weight of 300 to 520g/mol, (c3) an acrylic monomer having a number of double bonds as a bifunctional group having a weight average molecular weight of 320 to 500g/mol and containing a cyclic structure, and (c4) an acrylic monomer having a number of double bonds as a trifunctional group having a weight average molecular weight of 250 to 340g/mol and not containing a cyclic structure, and 3.
In a preferable scheme, the acrylic monomers with different molecular weights, different numbers of double bonds and different molecular structures are adopted as raw materials of the adhesive layer composition, and the applicant finds that the acrylic monomers with different numbers of double bonds, different molecular weights and different molecular structures are favorable for controlling the acting force between the adhesive layer composition and a base material in the experimental process, the formed adhesive tape is prevented from being layered, the adhesive force between the adhesive layer composition and a chip is prevented from being larger, the adhesive force between the adhesive layer and the chip is lower, in the actual operation process, (c1) the acrylic monomer with the weight average molecular weight of 200-350 g/mol and the single functionality, namely the double bond number of 1 is favorable for controlling the molecular weights of the formed acrylic prepolymer and the acrylic polymer when the adhesive layer is cured, the molecular weight and the viscosity of the system are prevented from being too large, and (c2) the acrylic monomer with the weight average molecular weight of 300-520 g/mol and the double functionality, namely the double bond number of 2 is favorable for, meanwhile, the phenomena of chip pollution and adhesive residue caused by the migration of unreacted monomers are avoided; and (c3) bifunctional acrylic monomers with the weight average molecular weight of 320-500 g/mol, namely the number of double bonds is 2, and the acrylic monomers with the cyclic structure, (c4) trifunctional acrylic monomers with the weight average molecular weight of 250-340 g/mol, namely the number of double bonds is 3, and (c2) are cooperated, so that the cohesion of the system is improved, and the mutual restraint is realized, and the excessive cohesion is controlled.
In order to control the reaction activity and the acting influence of different acrylic monomers in the reaction process, the better viscosity is realized before UV irradiation, and splashing in the wafer cutting process is avoided; and meanwhile, the wafer is easy to peel off after UV irradiation, the picking performance is good, the phenomenon of wafer pollution or residual glue is avoided, and the molar ratio of (c1), (c2), (c3) and (c4) is required to be controlled to be 1: (3.1-4.5): (0.35-0.62): (0.45-0.62).
More preferably, (c1) an acid value of an acrylic monomer having a monofunctional group with a weight average molecular weight of 200 to 350g/mol, i.e., the number of double bonds is 1, is not more than 0.5; preferably, the viscosity is 2 to 40cps at 25 ℃; further preferably, the surface tension is 20 to 35; (c1) the weight average molecular weight and the viscosity of the acrylic monomer are relatively low, the surface tension is close to or in gradient distribution with other acrylic monomers, and the difference between the surface tension and the surface tension is not large, so that the acrylic monomer has good fusion property in the reaction process, the reaction efficiency is improved, and the molecular weight of a system is controlled; specifically, (c1) is exemplified by, but not limited to:
Figure BDA0002597803810000031
(Changxing chemical EM-315-LM, weight average molecular weight 254g/mol, acid value less than or equal to 0.5; viscosity 4-8 cps at 25 deg.C; surface tension 28.9).
More preferably, (c2) an acid value of an acrylic monomer having a bifunctional group with a weight average molecular weight of 300 to 520g/mol, i.e., the number of double bonds of 2, of not more than 0.5; preferably, the viscosity is 5 to 85cps at 25 ℃; further preferably, the surface tension is 30 to 43; specifically, (c2) is exemplified by, but not limited to:
Figure BDA0002597803810000032
(Changxing chemical EM-228, weight average molecular weight 408g/mol, acid value less than or equal to 0.5; viscosity at 25 ℃ of 25-45 cps, surface tension of 39).
More preferably, (c3) the acid value of the acrylic monomer containing a cyclic structure and having a bifunctional group with a weight average molecular weight of 350 to 550g/mol, that is, the number of double bonds of 2 is not more than 0.5; preferably, the viscosity is 100 to 800cps at 25 ℃; further preferably, the surface tension is 28 to 40; specifically, for example, but not limited to:
Figure BDA0002597803810000033
(Changxing chemical EM-3261, weight average molecular weight of 540g/mol, acid value less than or equal to 0.5, viscosity of 500-800 cps at 25 ℃ and surface tension of 39); the weight average molecular weights of the acrylic monomers (c2) and (c3) are close to each other and slightly higher than (c1), the molecular weight of the prepolymer in the system is increased in the reaction process, and the molecular weight of the system is increased by the cooperation of the acrylic monomers containing the cyclic structure and the acrylic monomers not containing the cyclic structure, and the pollution to wafers or chips in the cutting and picking processes is reduced by molecular design.
More preferably, (c4) an acrylic monomer having a weight average molecular weight of 250 to 340g/mol and a trifunctional group not containing a cyclic structure, i.e., 3 double bonds, has an acid value of 0.5 or less; preferably, the viscosity is 50 to 200cps at 25 ℃; further preferably, the surface tension is 30 to 40; specifically, for example, but not limited to:
Figure BDA0002597803810000041
(Changxing chemical EM231-TF, weight average molecular weight 296g/mol, acid value less than or equal to 0.5; viscosity at 25 ℃ of 70-110 cps; surface tension of 35); the acrylic monomer with low viscosity and no ring structure and three functionality, namely 3 double bonds, is adopted, and the surface tension of the acrylic monomer is close to that of other acrylic monomers, so that the viscosity of a system is favorably reduced, the adhesive force between an adhesive layer and the surface of a base material is improved, the cohesive force of a polymer can be improved in the curing process, and the small molecules are prevented from overflowing.
The "viscosity" as referred to herein is the viscosity commonly used to refer to glues, and is kinematic viscosity, as measured by a brookfield viscometer.
Preferably, (d) the reactive group-containing acrylic monomer having a weight average molecular weight of 150 to 650g/mol includes (d1) an acrylic monomer having a reactive group number of 1, (d2) an acrylic monomer having a reactive group number of 2, (d3) an acrylic monomer having a reactive group number of 3 or more; further preferably, the reactive group is a hydroxyl group; according to the invention, acrylic monomers containing different active groups are adopted to jointly act with acrylic monomers without active groups and diisocyanate to form a prepolymer, and the density and cohesion of the prepolymer and the bonding capability of a wafer or a chip are influenced by the different active groups; in order to further improve the balance between the cohesive force and the bonding ability to the wafer or the chip, the molar ratio of (d1), (d2), (d3) is controlled to be 1: (2.3-3.2): (0.23-0.47).
As (d1) acrylic monomer having the number of reactive groups of 1, and the reactive groups are hydroxyl, for example but not limited to: hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, and the like.
As (d2) acrylic monomer having the number of reactive groups of 2 and the reactive groups being hydroxyl, there may be mentioned, for example but not limited to: tripropylene glycol diacrylate, 1, 6-ethylene glycol diacrylate, and the like.
As the (d3) acrylic monomer having 3 or more reactive groups and hydroxyl groups, for example, but not limited to: trimethylolpropane triacrylate, pentaerythritol triacrylate, and the like.
The diisocyanate is not particularly limited in the present invention, and examples thereof include, but are not limited to: aromatic diisocyanate: 4, 4' -diphenylmethane diisocyanate, 1, 4-xylylene diisocyanate, 4' -diphenylmethyl diisocyanate, 2, 4-tolylene diisocyanate, 2, 6-tolylene diisocyanate, 4' -toluidine diisocyanate, 2, 4, 6-isocyanatotoluene, 1, 3, 5-triisocyanatobenzene, dianisidine isocyanate, 4' -diphenyl ether diisocyanate, 4', 4 ″ -triphenylmethane triisocyanate; alicyclic diisocyanate: 1, 3-cyclohexane diisocyanate, 1, 4-cyclohexane diisocyanate, methyl-2, 6-cyclohexane diisocyanate, 4' -methylenebis (cyclohexyl isocyanate), 1, 4-bis (isocyanotomethyl) cyclohexane, and the like.
The polymerization initiator is a photoinitiator, and the monomer polymerization is initiated under the UV irradiation to cure the adhesive layer composition, wherein the photoinitiator can be acetophenones, anthraquinones, thioxanthones and the like, wherein the acetophenones include benzoin alkyl ethers, acetophenone, 2-dimethoxy-2-acetophenone, 2-diethoxy-2-acetophenone, 1-dichloroacetophenone and the like; examples of the anthraquinones include 2-methylanthraquinone, 2-ethylanthraquinone, 2-tert-butylanthraquinone, and 1-chloroanthraquinone; examples of the thioxanthones include 2, 4-dimethylthioxanthone, 2, 4-diisopropylthioxanthone, 2-chlorothioxanthone, and 2, 4-diisopropylthioxanthone; preferably, it accounts for 0.05 to 0.1 wt% of the acrylic prepolymer; when the content of the adhesive is less, the cohesive force of the adhesive layer composition is lower, and the problems of adhesive residue and pollution are easy to occur; when the content of the additive is higher, the cohesive force is higher, and the phenomenon of splashing in the cutting process occurs.
The preparation method of the acrylic prepolymer disclosed by the invention comprises the following steps: mixing (c) acrylic monomers without active groups and with the weight-average molecular weight of 200-800 g/mol, (d) acrylic monomers with active groups and with the weight-average molecular weight of 150-650 g/mol, and (e) diisocyanate, and heating and reacting for 4.5-6.5 h at 50-60 ℃ to obtain the high-performance acrylic resin.
The conditions used for UV curing of the photocurable coating composition of the present invention may be well known to those skilled in the art, for example, irradiation with an ultraviolet lamp at an illuminance of 5mW/cm2(ii) a And completely curing the mixture.
In the actual use process, additives such as a softening agent, an aging inhibitor, a filler, a conductive agent, an ultraviolet absorber, a light stabilizer and the like may be added to the adhesive layer composition according to actual needs.
The second aspect of the invention provides an adhesive containing the photo-curable adhesive layer composition.
The third aspect of the present invention provides an adhesive tape comprising the photocurable adhesive layer composition; the adhesive tape sequentially comprises a base material layer, an adhesive layer and a release layer from bottom to top, and the adhesive layer is formed by a photocuring adhesive layer composition.
Examples of the material of the substrate layer include polyvinyl chloride, polyethylene terephthalate, ethylene-vinyl acetate copolymer, ethylene acrylic acid-acrylic ester film, ethylene ethyl acrylate copolymer, polyethylene, polypropylene, propylene-based copolymer, ethylene acrylic acid copolymer, and the like; the substrate film may be a single-layer or multi-layer film or sheet composed of the above materials, or may be obtained by laminating films composed of different materials; the thickness of the base material film is 50 to 150 μm, preferably 70 to 120 μm.
Examples of the release layer material include polyvinyl chloride, polyethylene terephthalate, ethylene-vinyl acetate copolymer, ethylene acrylic acid-acrylic ester film, ethylene ethyl acrylate copolymer, polyethylene, polypropylene, propylene-based copolymer, ethylene acrylic acid copolymer, and the like; the substrate film may be a single-layer or multi-layer film or sheet composed of the above materials, or may be obtained by laminating films composed of different materials; the thickness of the base material film is 50 to 200 μm.
Has the advantages that:
(1) the components have better compatibility in the process of preparing the acrylic prepolymer by adopting the acrylic monomer with specific molecular weight, viscosity and surface tension, and the overflow and migration of small molecules are reduced, so that the storage time of the adhesive layer composition is prolonged, and the pollution to wafers or chips is reduced;
(2) the acrylic prepolymer prepared by adopting different types of acrylic monomers is beneficial to realizing better viscosity before UV irradiation and avoiding splashing in the wafer cutting process;
(3) the acrylic monomer with specific molecular weight, viscosity and surface tension and the polymerization initiator with specific content are adopted to act synergistically, so that the adhesive layer interface has good adhesive property, is easy to peel after UV irradiation, the adhered object has good pickup property, and the problems of wafer pollution or residual adhesive are avoided.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following detailed description, but those skilled in the art will understand that the following described examples are some, not all, of the examples of the present invention, and are only used for illustrating the present invention, and should not be construed as limiting the scope of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The following raw materials were used as components in the examples:
a: the polymerization initiator is acetophenone;
b: the diisocyanate is 4, 4' -diphenyl ether diisocyanate;
c: acrylic monomers free of reactive groups
C1：
Figure BDA0002597803810000071
Purchased from Changxing chemical EM-315-LM, with weight average molecular weight of 254g/mol and acid value less than or equal to 0.5; the viscosity is 4-8 cps at 25 deg.C; surface tension 28.9;
C2：
Figure BDA0002597803810000072
purchased from Changxing chemical EM-228, the weight-average molecular weight is 408g/mol, and the acid value is less than or equal to 0.5; the viscosity is 25-45 cps at 25 deg.C; a surface tension of 39;
C3：
Figure BDA0002597803810000073
purchased from Changxing chemical EM-3261, with weight average molecular weight of 540g/mol and acid value less than or equal to 0.5; the viscosity is 500 to 800cps at 25 ℃; a surface tension of 39;
C4：
Figure BDA0002597803810000075
purchased from Changxing chemical EM231-TF, the weight average molecular weight is 296g/mol, and the acid value is less than or equal to 0.5; the viscosity is 70 to 110cps at 25 ℃; a surface tension of 35;
C5：
Figure BDA0002597803810000076
purchased from Changxing chemical EM 2107, with weight average molecular weight of 310g/mol and acid value less than or equal to 0.5; the viscosity is 130 to 170cps at 25 ℃;
C6：
Figure BDA0002597803810000077
purchased from changxing chemical EM 235; the viscosity is 400-550 cps at 25 ℃;
C7：
Figure BDA0002597803810000078
purchased from Changxing chemical EM 320, with the weight-average molecular weight of 198g/mol and the acid value less than or equal to 0.5; the viscosity is 100 to 300cps at 25 ℃;
d acrylic monomer containing reactive group:
d1: hydroxyethyl methacrylate;
d2: 1, 6-ethylene glycol diacrylate;
d3: pentaerythritol triacrylate.
Example 1
Embodiment 1 of the present invention provides a photo-curable coating composition, including a component a and an acrylic prepolymer, wherein the component a accounts for 1.5 wt% of the acrylic prepolymer; the acrylic prepolymer is formed by a component B, a component C and a component D, wherein the weight ratio of the component C to the component D to the component B is 1: 0.75: 0.56;
the component C comprises C1, C2, C3 and C4; the molar ratio of C1 to C2 to C3 to C4 is 1: 4.5: 0.62: 0.59;
the component D comprises D1, D2 and D3; the molar ratio of D1, D2 and D3 is 1: 3.2: 0.47.
example 2
Embodiment 2 of the present invention provides a photo-curable coating composition, including a component a and an acrylic prepolymer, wherein the component a accounts for 0.1 wt% of the acrylic prepolymer; the acrylic prepolymer is formed by a component B, a component C and a component D, wherein the weight ratio of the component C to the component D to the component B is 1: 0.55: 0.45 of;
the component C comprises C1, C2, C3 and C4; the molar ratio of C1 to C2 to C3 to C4 is 1: 3.5: 0.35: 0.45 of;
the component D comprises D1, D2 and D3; the molar ratio of D1, D2 and D3 is 1: 2.3: 0.23.
example 3
Embodiment 3 of the present invention provides a photo-curable coating composition, including a component a and an acrylic prepolymer, wherein the component a accounts for 0.55 wt% of the acrylic prepolymer; the acrylic prepolymer is formed by a component B, a component C and a component D, wherein the weight ratio of the component C to the component D to the component B is 1: 0.68: 0.52;
the component C comprises C1, C2, C3 and C4; the molar ratio of C1 to C2 to C3 to C4 is 1: 3.9: 0.56: 0.49;
the component D comprises D1, D2 and D3; the molar ratio of D1, D2 and D3 is 1: 2.8: 0.42.
example 4
Example 4 of the present invention provides a photocurable overcoat composition, which is similar to example 3 except that C1 is replaced with C5.
Example 5
Example 5 of the present invention provides a photocurable overcoat composition, which is similar to example 3 except that C4 is replaced with C6.
Example 6
Example 6 of the present invention provides a photocurable overcoat composition, which is substantially the same as example 3, except that the amount of C3 is 0.
Example 7
Example 7 of the present invention provides a photocurable overcoat composition, which is substantially the same as example 3, except that the amount of C2 is replaced with C7.
Example 8
Embodiment 8 of the present invention provides a photocurable glue layer composition, which is the same as embodiment 3 in the following specific point that the molar ratio of C1, C2, C3 and C4 is 1: 3.9: 0.9: 0.8.
example 9
Example 9 of the present invention provides a photocurable overcoat composition, which is substantially the same as example 3, except that the amount of D3 is replaced with hydroxyethyl methacrylate.
Example 10
Example 10 of the present invention provides a photocurable overcoat composition in accordance with the same embodiment as example 3, except that component a comprises 5.5 wt% of the acrylic prepolymer.
The preparation method of the acrylic prepolymer in the embodiments 1 to 10 comprises the following steps: and mixing the component B, the component C and the component D, and heating and reacting for 4.5-5.5 hours at 50-60 ℃ to obtain the high-performance high-temperature-resistant high-performance high-temperature-resistant.
Performance evaluation
Coating the photo-curing adhesive layer composition obtained in the embodiment 1-10 on a base material film of polyethylene terephthalate for coating work to dry the adhesive layer to a thickness of 20 μm, and drying the adhesive layer for 5min at 90 ℃; then attaching a release film of polyethylene terephthalate on the surface of the adhesive layer composition, and curing for 48 hours at 60 ℃ to obtain the adhesive tape; wherein the thickness of the base film is 110 μm, and the thickness of the release film is 90 μm.
The adhesive tapes obtained in examples 1 to 10 were used to bond a ceramic having a length of 80mm, a width of 80mm and a thickness of 0.6mm to an annular frame, and then, each of the cutting and picking-up steps was performed, and the state of the chip in the cutting and picking-up steps was observed:
1. chip splash: the residual ratio of the ceramic chip held on the adhesive sheet after the dicing step was evaluated according to the following criteria:
excellent: the chip flying is less than 5%;
o (good): the chip flying is more than 5% and less than 10%;
x (not): the chip scattering is 10% or more.
2. Pickup property: the evaluation was made according to the following criteria based on the proportion of the ceramic chips that could be picked up in the picking-up step:
excellent: the success rate of picking up the chip is more than 95%;
o (good): the success rate of picking up the chip is more than 80% and less than 95%;
x (not): the success rate of chip pick-up is lower than 80%.
3. Loosening the chip: based on the loosening ratio of the semiconductor chip adjacent to the semiconductor chip to be picked up in the picking-up process due to the impact of the pin projection, evaluation was performed according to the following criteria:
excellent: chip looseness is less than 1%;
o (good): the chip looseness is more than 1% and less than 3%;
x (not): the chip looseness is more than 3%.
4. The phenomenon of adhesive residue: the adhesive scraping was performed by selecting 50 picked up chips at random, observing the side surfaces of the chips with a 500-fold microscope, and evaluating whether or not the adhesive was adhered to the side surfaces of the chips according to the following criteria:
excellent: the adhesive did not adhere on the chip side;
o (good): adhesion of the adhesive on the chip side is less than 5%;
x (not): the adhesion of the adhesive to the chip side is 5% or more.
Table 1 results of performance testing
Figure BDA0002597803810000101
Figure BDA0002597803810000111
The foregoing examples are merely illustrative and serve to explain some of the features of the method of the present invention. The appended claims are intended to claim as broad a scope as is contemplated, and the examples presented herein are merely illustrative of selected implementations in accordance with all possible combinations of examples. Accordingly, it is applicants' intention that the appended claims are not to be limited by the choice of examples illustrating features of the invention. Also, where numerical ranges are used in the claims, subranges therein are included, and variations in these ranges are also to be construed as possible being covered by the appended claims.

Claims (10)

1. A photo-curing glue layer composition is characterized in that the raw materials comprise:
(a) an acrylic prepolymer;
(b) a polymerization initiator which accounts for 0.05 to 1.5 wt% of the acrylic prepolymer;
wherein the acrylic prepolymer is formed by raw materials of (c) acrylic monomer without active group with the weight-average molecular weight of 200-800 g/mol, (d) acrylic monomer with active group with the weight-average molecular weight of 150-650 g/mol and (e) diisocyanate; and the active group comprises any one or more of amino, hydroxyl, carboxyl, amido, phenolic hydroxyl and maleic anhydride.
2. The photocurable coating composition of claim 1, wherein the (c) acrylic monomer having a weight average molecular weight of 200 to 800g/mol and not containing an active group comprises (c1) an acrylic monomer having a weight average molecular weight of 200 to 350g/mol and having a number of monofunctional double bonds of 1, (c2) an acrylic monomer having a weight average molecular weight of 300 to 520g/mol and having a number of bifunctional double bonds of 2, (c3) an acrylic monomer having a weight average molecular weight of 320 to 500g/mol and having a cyclic structure and having a number of bifunctional double bonds of 2, and (c4) an acrylic monomer having a weight average molecular weight of 250 to 340g/mol and not containing a cyclic structure and having a number of trifunctional double bonds of 3.
3. The photocurable overcoat composition of claim 2 wherein (c1) an acrylic monomer having a weight average molecular weight of 200 to 350g/mol and a monofunctional number of 1 double bonds has an acid value of 0.5 or less; preferably, the viscosity is 2 to 40cps at 25 ℃; further preferably, the surface tension is 20 to 35.
4. The photocurable overcoat composition of claim 2 wherein (c2) the acrylic monomer having a weight average molecular weight of 300 to 520g/mol and a bifunctional group with a number of double bonds of 2 has an acid value of 0.5 or less; preferably, the viscosity is 5 to 85cps at 25 ℃; further preferably, the surface tension is 30 to 43.
5. The photocurable overcoat composition of claim 2 wherein (c3) the acrylic monomer having a weight average molecular weight of 350 to 550g/mol, which has a bifunctional group with a double bond number of 2 and a cyclic structure, has an acid value of 0.5 or less; preferably, the viscosity is 100 to 800cps at 25 ℃; further preferably, the surface tension is 28 to 40.
6. The photocurable overcoat composition of claim 2 wherein (c4) an acrylic monomer having a weight average molecular weight of 250-340 g/mol and a trifunctional group without a cyclic structure, i.e., 3 double bonds, has an acid number of 0.5 or less; preferably, the viscosity is 50 to 200cps at 25 ℃; further preferably, the surface tension is 30 to 40.
7. The photocurable overcoat composition of any one of claims 2-6 wherein the molar ratio of (c1), (c2), (c3) and (c4) is 1: (3.1-4.5): (0.45-0.62): (0.45-0.62).
8. The photocurable overcoat composition of any one of claims 2-7 wherein the (d) reactive group-containing acrylic monomer having a weight average molecular weight of 150-650 g/mol comprises (d1) 1 reactive group number of acrylic monomer, (d2) 2 reactive group number of acrylic monomer, and (d3) 3 reactive group number of acrylic monomer.
9. An adhesive comprising the photocurable adhesive layer composition according to any one of claims 1 to 8.
10. An adhesive tape comprising the photocurable adhesive layer composition according to any one of claims 1 to 8.
CN202010714952.5A 2020-07-23 2020-07-23 Photocuring adhesive layer composition, adhesive and adhesive tape Withdrawn CN111808559A (en)

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