Adhesion Performance and UV-Curing Behaviors of Interpenetrated Structured Pressure Sensitive Adhesives with 3-MPTS for Si-Wafer Dicing Process

Abstract

As Si-wafers, as used in the electronic industry, become thinner and thinner, it is important to investigate the conditions which are suitable for easily peelable acrylic dicing tapes. In the ‘pick-up’ process, the adhesion strength decreased after UV irradiation as a result of polymer network formation. In this study, interpenetrating polymer network (IPN) structured acrylic pressure sensitive adhesives (PSAs) were investigated with two different types of UV irradiation — a steady UV irradiation and a pulsed UV irradiation of 100 mJ/cm². The PSAs binder contained 2-ethylhexyl acrylate (2-EHA), acrylic acid (AA) and 3-methacryloxypropyl trimethoxysilane (3-MPTS). The hexafunctional monomer, dipentaerythritol hexacrylate (DPHA) and 3-methacryloxypropyl trimethoxysilane (3-MPTS) were used as diluent monomers. The adhesion performance as related to the peel strength and the tack properties on the Si-wafer substrates, was examined with increasing UV dose. The effect of UV-curing on the behavior and viscoelastic properties of the ‘pick-up’ acrylic tapes was investigated using Fourier transform infrared — attenuated total reflectance spectroscopy (FTIR–ATR) and an advanced rheometric expansion system (ARES). It is also necessary to consider the contaminants on the Si-wafer substrates left behind after releasing the dicing tapes, because of possible damage to the Si-wafers and subsequent processes. Field emission scanning electron microscopy (FE-SEM) and X-ray photoelectron spectroscopy (XPS) analysis revealed little residue on the Si-wafer after removing the tapes and after more than the specific level of UV dose.     

Sustainable isosorbide‐based transparent pressure‐sensitive adhesives for optically clear adhesive and their adhesion performance

A biomass‐based isosorbide acrylate (ISA) was synthesized in a one‐pot reaction at low temperature with a quite slow dropwise technique using a syringe pump. Using the ISA monomer, UV‐cured transparent acrylic pressure‐sensitive adhesives (PSAs) composed of semi‐interpenetrating networks were prepared. The effect of ISA on the adhesion performance of the resulting acrylic PSAs was investigated by changing the ISA content, while fixing the mole ratio between 2‐ethylhexyl acrylate and 2‐hydroxyethyl acrylate in the PSAs. The prepared acrylic PSAs, with ISA content ranging from 3.2 to 14.3 mol%, were evaluated in terms of 180° peel strength, probe tack, static shear testing and optical properties. Increasing the ISA content in the acrylic PSAs improved the adhesion properties, such as 180° peel strength (0.25–0.32 N/25 mm), shear holding power (0.086–0.023 mm) and probe tack (1.21–2.26 N). Dynamic mechanical analysis indicated that ISA is a good candidate monomer, playing the role of adhesion promoter and hard monomer in the acrylic PSAs. © 2017 Society of Chemical Industry     

Adhesion performance of UV-cured semi-IPN structure acrylic pressure sensitive adhesives

UV-curable solvent-free pressure sensitive adhesives (PSAs) are gaining importance in the area of adhesives because of increasing environmental concerns and the goal to reduce volatile organic compounds (VOCs) in work areas and consumption places. These PSAs have advantages such as low emission of VOCs, a solvent-free process, a fast producton rate at ambient temperature and only a modest requirement for operating space. In this study, UV-curable PSAs were investigated by measuring their adhesion performance in terms of probe tack, peel strength, shear adhesion failure temperature (SAFT) and holding power. PSAs were synthesized from 2-ethylhexyl acrylate (2-EHA), acrylic acid (AA) and vinyl acetate (VAc), using variations in AA concentration to control the glass transition temperature (T _g) of the prepared PSAs. In addition, two types of trifunctional monomers, trimethylolpropane triacrylate (TMPTA) and trimethylolpropane ethoxylated (6) triacrylate (TMPEOTA), which have different chain lengths, were used to form semi-interpenetrating polymer network (semi-IPN) structures after UV exposure. With increasing AA concentration in the PSAs, both the T _g and viscosity increased. Also, probe tack and SAFT increased, but peel strength decreased. After UV irradiation, probe tack decreased, and SAFT and peel strength increased as AA concentration increased in the PSAs. In most cases, cohesive failure changed to interfacial failure after UV exposure. Also, TMPTA increased the cohesion of PSAs; however, TMPEOTA affected the mobility of PSAs due to the different chain lengths of the two types of trifunctional monomer in a different way. The increase of TMPEOTA content diminished the cohesion of PSAs. Consequently, the adhesion performance of the PSAs was closely related to the T _g of the PSAs, and the two types of trifunctional monomer showed different adhesion performances.     

Effect of naphthyl curing agent having thermally stable structure on properties of UV-cured pressure sensitive adhesive

Pressure sensitive adhesives (PSAs) with higher thermal stability were synthesized by crosslinking acrylic copolymer with naphthyl curing agent. The acrylic copolymer was synthesized for a base resin of PSAs by solution polymerization of 2-ethylhexyl acrylate, ethyl acrylate, and acrylic acid with N,N′-azobisisobutyronitrile as an initiator. The acrylic copolymer was further modified with glycidyl methacrylate to have the vinyl groups available for UV curing. Thermal stability of acrylic PSAs was improved noticeably with increasing naphthyl curing agent content and UV dose mainly due to the extensive formation of crosslinked structure in the polymer matrix. Although the peel strength decreased with UV curing of acrylic polymer, a proper balance between the thermal stability and the adhesion performance of PSAs was obtained by controlling the UV curing with naphthyl curing agent content and UV dose.     

Optical properties and UV-curing behaviors of optically clear semi-interpenetrated structured acrylic pressure sensitive adhesives

Acrylic pressure-sensitive adhesives (PSAs) with different side-chain lengths in the co-monomer were synthesized. This study employed semi-interpenetrated structured polymer networks using UV-curing with a hexafunctional monomer, dipentaerythritol hexacrylate (DPHA). The optical properties of the acrylic PSAs were examined by UV-visible spectroscopy and a prism coupler. ARES was used to characterize the viscoelastic properties of the acrylic PSAs. Adhesion performance was conducted by the peel strength and probe tack tests. Also UV-curing behavior of the acrylic PSAs was investigated by FTIR.     

Thermal stability and surface properties of acrylic PSAs modified by hexafluorobutyl acrylate

The article attempted to prepare special acrylic adhesives with preferable adhesion property and better thermal stability by introducing a fluorinated monomer. The FT-IR result showed that fluorinated monomers and acrylic monomers participated in copolymerization successfully. Furthermore, fluorinated groups performed good compatibility with acrylic resins, based on differential scanning calorimetry curve. According to the TG test under different heating rates, the activation energy of PSAs containing different content of fluorinated monomers was calculated to evaluate the effect of hexafluorobutyl acrylate on heat resistance of PSAs. Then, the findings of contact angle test revealed that the fluorinated PSAs also had rather lower surface energy than ordinary PSAs. Finally, the results of peel strength measurements indicated that the fluorinated PSAs demonstrated excellent adhesion property on various materials, especially low surface energy substrates.     

Wettability and adhesion characteristics of photo-crosslinkable adhesives for thin silicon wafer

Acrylic pressure-sensitive adhesives (PSAs) have many applications in the processes of electronic industry. As the silicon wafers become thinner, the acrylic PSAs need to show proper adhesion and better wettability on the thin wafer. The acrylic copolymers were synthesized by solution polymerization of 2-ethylhexyl acrylate, ethyl acrylate, and acrylic acid with AIBN as an initiator. Photo-crosslinkable PSAs were synthesized by reaction of the acrylic copolymers with glycidyl methacrylate (GMA) and lauryl glycidyl ether (LGE). The adhesion performance of acrylic photo-crosslinkable PSAs was investigated based on wettability, probe tack, peel strength, cohesiveness, and viscoelastic properties. The adhesion characteristics varied significantly depending on the ratio of GMA to LGE in the photo-crosslinkable PSAs.     

Fabrication of optically clear acrylic pressure–sensitive adhesive by photo-polymerization: UV-curing behavior,adhesion performance,and optical properties

Acrylic pressure–sensitive adhesives (PSAs) with 2-phenoxy ethyl acrylate (PEA) were polymerized using UV-curing technology. This study examined the effects of PEA content and UV dose. The photo-polymerization behavior of the pre-polymer was examined by viscosity measurements, real-time Fourier transform infrared spectroscopy, and photo-differential scanning calorimetry. The curing behaviors of the acrylic PSAs were investigated by shrinkage test, a modular advanced rheometer system, and gel content. differential scanning calorimetry and Advanced Rheometric Expansion System were used to characterize the acrylic PSAs. Adhesion performances were measured by probe tack, peel strength, and shear adhesion failure temperature. The optical properties of acrylic PSAs were examined by UV–visible spectroscopy and prism coupler. The PEA content had a larger effect on improving the optical properties, than did the UV dose. The transmittances of the acrylic PSAs with <75% PEA were >95%. The refractive indices of the acrylic PSAs increased with increasing PEA content, due to its high refractive index, >1.5, which affected the overall refractive indices, particularly in the visible region.     

Effect of side chain on wettability and adhesion performance of acrylic pressure-sensitive adhesives on thin silicon wafer

Acrylic pressure-sensitive adhesives (PSAs) need to show proper adhesion and improved wettability on the silicon wafer as the wafer becomes thinner. The acrylic copolymers were synthesized by solution radical polymerization of 2-ethylhexyl acrylate, ethyl acrylate, and acrylic acid with AIBN as an initiator. Adhesion performance and wettability of acrylic PSAs were studied depending on the content of lauryl side chains and the degree of crosslinking. The introduction of lauryl side chain was characterized by Fourier transform infrared spectroscopy. The adhesion performance of acrylic PSAs having lauryl side chain was investigated using contact angle, wettability, probe tack, peel strength, and cohesiveness tests. The wettability of acrylic PSAs was improved significantly with increasing the content of lauryl side chain.     

Adhesion Performance and Thermal Stability of Fluorinated PSAs as a Crosslinking System

The use of pressure sensitive adhesives (PSAs) is becoming increasingly popular in many industrial fields. In the automobile industry the main reasons for using PSAs are that they reduce the overall weight of the vehicles and because they are easy to use. However, in the case of acrylic PSAs, the non-crosslinked linear chains results in low thermal stability. In this study, a fluorinated acrylic pressure sensitive adhesive was synthesized under UV irradiation and crosslinking was applied to the linear chain of acrylic PSAs to improve the thermal stability. The adhesion performance was evaluated by analyzing the peel strength, probe tack and shear adhesion failure temperature (SAFT) as a function of the type of crosslinking system. In particular, the peel strength and probe tack were measured at 25, 50 and 80°C. The viscoelastic properties, which were measured using an advanced rheometric expansion system (ARES), revealed a proper balance between the thermal stability and adhesion performance.     

丁腈橡胶／丙烯酸酯UV固化压敏胶的研究

将丁腈橡胶溶于丙烯酸酯类混合单体中制成胶液，在常温下涂布于基材后进行紫外光辐照制备压敏胶带。采用红外光谱对UV辐照下的聚合过程进行了扫描分析并提出了固化机理。研究了光引发剂、UV辐照剂量、体系组成等对压敏胶带综合性能的影响。     

Optical properties and adhesion performance of acrylic PSAs; influence of functionalized monomer and curing agent

Acrylic pressure–sensitive adhesives (PSAs) were synthesized by solution polymerization using zirconium carboxyethyl acrylate (ZrCEA) with methyl aziridine derivatives (MAZ) as a curing agent. The acrylic PSAs were characterized by Fourier transform-infrared spectroscopy and gel contents. The viscoelastic properties of the acrylic PSAs were determined using an advanced rheometric expansion system. The adhesion performance of the acrylic PSAs was determined by measuring the probe tack, peel strength, shear adhesion failure temperature, and holding power. The optical properties of the acrylic PSAs were evaluated by the transmittance and refractive index. The results show that the adhesion performance and optical properties of the acrylic PSAs are influenced by the ZrCEA and MAZ content.     

Improvement in wettability of pressure‐sensitive adhesive on silicon wafer using crosslinking agent with siloxane groups

Acrylic copolymers are prepared by radical polymerization of 2‐ethylhexyl acrylate, ethyl acrylate, and acrylic acid followed by crosslinking to manufacture the pressure‐sensitive adhesives (PSAs) for silicon wafer protection. Both higher reliability and wettability are required for the protective acrylic PSAs in the semiconductor processing applications. The siloxane linkages are introduced in the acrylic PSAs via crosslinking with siloxane‐containing crosslinking agent to modify the thermal and wetting properties of PSAs efficiently. The more efficient formation of crosslinked network structure was achieved with higher content of tetra‐functional crosslinking agent, and the surface energy of PSAs decreased significantly with increasing the content of siloxane linkage resulting in the improved areal wetting rate. The thermal stability of PSAs was also improved significantly by incorporation of siloxane linkages. The adhesion properties such as peel strength and probe tack of acrylic PSAs decreased significantly by increasing the content of either crosslinking agent or siloxane linkage. The acrylic PSA with siloxane group showed both satisfactory wetting and clean debonding properties for the optimal protection of thin silicon wafers. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013     

Lamination of high‐density polyethylene by bulk photografting and the mechanism of adhesion

The photolamination of high‐density polyethylene (HDPE) by bulk photografting is described, along with a discussion of the adhesion mechanism. HDPE can be photolaminated very easily with a thin poly(acrylic acid) layer, photopolymerized from acrylic acid, with very strong adhesion obtained after a short time of UV irradiation; the adhesion failure mode is polyethylene breakage. Thicker HDPE sheets require longer irradiation times for strong adhesion. Methacrylic acid or hydroxyethyl methacrylate provides no adhesion of HDPE at all after irradiation. When glycidyl acrylate is used alone between HDPE sheets, the peel strength of the photolaminated polyethylene is only approximately 320 N/m, but when glycidyl acrylate or hydroxyethyl methacrylate is grafted with acrylic acid, very good adhesion can be obtained. It is proposed that stronger adhesion is produced by a less branched grafted chain structure, which permits much more chain entanglement. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci 97: 1097–1106, 2005     

Eco-friendly UV-curable pressure sensitive adhesives containing acryloyl derivatives of monosaccharides and their adhesive performances

Two different monosaccharide acrylate monomers were designed and synthesized from glucose and galactose, and were then used to prepare transparent acrylic pressure sensitive adhesives (PSAs) comprised of semi-interpenetrated structured polymer networks. The effects of the monosaccharide architecture in the acrylate monomers on the adhesive performance of the acrylic PSAs were investigated. Prepared UV-curable acrylic PSA syrups were characterized and the optical properties of the acrylic PSAs were also examined. All of the acrylic PSAs exhibited high transparency in the visible wavelength region. With increasing monosaccharide acrylate concentration in the acrylic PSAs, adhesive performances such as the peel strength, cohesion strength, and probe tack were increased. However, there was no difference in their adhesive performances regardless of the different chemical structures of monosaccharide acrylate monomers.     

Novel pyridinium photoinitiators and their applications for the ultraviolet crosslinking of acrylic pressure‐sensitive adhesives

The demand for ultraviolet (UV)‐crosslinkable pressure‐sensitive adhesives (PSAs) has rapidly been increasing. A variety of different PSAs containing new photoreactive pyridinium derivatives have been evaluated for their effectiveness in improving adhesion and cohesion in UV‐crosslinkable PSAs. PSAs have been evaluated with respect to the tack, peel adhesion, and shear strength. This article summarizes the breakthrough technology used to achieve better performances in UV‐crosslinkable acrylic PSAs. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2007     

Viscoelastic and adhesive properties of single‐component thermo‐resistant acrylic pressure sensitive adhesives

Poly(butyl acrylate‐vinyl acetate‐acrylic acid) based acrylic pressure sensitive adhesives (PSAs) were synthesized by solution polymerization for the fabrication of high performance pressure sensitive adhesive tapes. The synthesized PSAs have high shear strength and can be peeled off substrate without residues on the substrate at temperature up to 150°C. The PSAs synthesized in the present work are single‐component crosslinked and they can be used directly once synthesized, which is convenient for real applications compared to commercial multi‐component adhesives. The results demonstrated that the viscosity of the PSAs remained stable during prolonged storage. The effects of the preparation conditions such as initiator concentration, cross‐linker amount, organosiloxane monomer amount and tackifier resin on the polymer properties, such as glass transition temperature (T_g), molecular weight (M_w), surface energy and shear modulus, were studied, and the dependence of the adhesive properties on the polymer properties were also investigated. Crosslinking reactions showed a great improvement in the shear strength at high temperature. The addition of tackifier resin made peel strength increase compared to original PSAs because of the improvement of the adhesion strength. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014 , 131, 40086.     

Optical properties and adhesion performance of optically clear acrylic pressure sensitive adhesives using chelate metal acetylacetonate

Optically clear acrylic pressure-sensitive adhesives (PSAs) with different co-monomers were synthesized. This study employed metal chelate aluminum acetylacetonate and zirconium acetylacetonate as curing agents. The optical properties of the acrylic PSAs were examined by UV–visible spectroscopy and a prism coupler. In addition, the adhesion performance was obtained by assessing the peel strength, the tack, and the shear adhesion failure temperature. The decrease in the adhesion performance may be related to a higher crosslinking density, which also resulted in a higher gel content.     

Solventless UV crosslinkable acrylic pressure sensitive adhesives

The synthesis and characterization of solventless acrylic UV crosslinkable pressure sensitive adhesives are presented. Different prepolymers were synthesized using bulk polymerization procedure. The reaction mixture consisted of acrylic monomers (2-ethylhexyl acrylate, acrylic acid and t-butyl acrylate), azobisisobutyronitrile initiator, chain transfer agent n-dodecylmercaptan and unsaturated UV photoinitiator 4-acryloyloxybezophenone, which was copolymerized into polymer backbone. Different formulations were tested and the prepolymer was characterized by viscosity measurements and final monomer conversions. The prepolymers were coated onto PET foil and crosslinked by application of UV light source. Peel adhesion at 180° on glass plate was measured. Gel phase was determined using the Soxhlet extraction and copolymer glass transition temperatures (T_g) were analyzed by differential scanning calorimetry (DSC). Results showed that the final monomer conversions in highly exothermic bulk polymerization reached a level between 75% and 90%. Prepolymer viscosity was highly influenced by change in polymer molecular weight and by addition of acrylic acid as a comonomer. On the other hand, the viscosity remained at the low level when t-butyl acrylate was used. The amount of gel phase for all adhesives was above 60 wt.%. Peel strength measurements showed decrease in peel strength with decreasing polymer molecular weight and increase of peel, when acrylic acid was used as a comonomer. All adhesive coatings with t-butyl acrylate comonomer showed cohesive failure.     

Synthesis of high‐solid‐content,acrylic pressure‐sensitive adhesives by solvent polymerization

In this study, we prepared high solid content (SC), solvent‐based, acrylic pressure‐sensitive adhesives (PSAs) with n‐dodecyl mercaptan as a chain‐transfer agent (CTA) and studied the crosslinking reactions between the crosslinker and the acrylic PSAs. Acrylic PSAs were prepared from 2‐ethyl hexyl acrylate, acrylic acid (AA), and 2‐azobisisobutyronitrile with a solution polymerization process. The results show AA resulted in an effective molecular weight in the acrylic PSAs, as it improved the hydrophilicity with increasing peel strength of the acrylic PSAs. As for the high SC, the molecular weight and system viscosity decreased through the addition of CTA. At a constant AA amount, the addition of CTA decreased the molecular weight and increased the hydrophobicity of the acrylic PSAs; this decreased the peel strength of the acrylic PSAs on the glass. Furthermore, the addition of CTA decreased the molecular weight and improved the acrylic PSAs' surface morphologies and optical properties. The acrylic PSAs produced in this study could meet production needs. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018 , 135, 46257.