JP6547632B2 - 接着剤組成物、接着剤組成物から得られる樹脂硬化物、接着剤組成物を用いた半導体装置の製造方法、及び固体撮像素子 - Google Patents
接着剤組成物、接着剤組成物から得られる樹脂硬化物、接着剤組成物を用いた半導体装置の製造方法、及び固体撮像素子 Download PDFInfo
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- JP6547632B2 JP6547632B2 JP2015560015A JP2015560015A JP6547632B2 JP 6547632 B2 JP6547632 B2 JP 6547632B2 JP 2015560015 A JP2015560015 A JP 2015560015A JP 2015560015 A JP2015560015 A JP 2015560015A JP 6547632 B2 JP6547632 B2 JP 6547632B2
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Classifications
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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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
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- C—CHEMISTRY; METALLURGY
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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- 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
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- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09J133/00—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
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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
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- C09J133/00—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
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- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
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- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
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- H01L24/95—Batch processes at chip-level, i.e. with connecting carried out on a plurality of singulated devices, i.e. on diced chips
- H01L24/97—Batch processes at chip-level, i.e. with connecting carried out on a plurality of singulated devices, i.e. on diced chips the devices being connected to a common substrate, e.g. interposer, said common substrate being separable into individual assemblies after connecting
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Description
また、本明細書において「透明性」とは、接着剤組成物と可視光線との間に相互作用が起こりにくく、電磁波の吸収及び散乱が生じにくいことを意味する。「透明性」の指標としては、入射光と透過光の強度比を百分率で表した透過率を用いる。透過率は対象とする光の波長によって異なるが、本明細書では可視光線を対象とする。可視光線に相当する電磁波とは、JIS Z8120の定義により、下界はおおよそ400nm、上界はおおよそ760nmである。
本実施形態に係る接着剤組成物は、(a)少なくとも2つのエチレン性不飽和基を有する化合物、(b)熱重合開始剤、(c)ヒンダードフェノール系化合物、(d)チオエーテル系化合物、及び、(e)チオール基を有する化合物、を含有する。なお、本明細書において、これらの成分は、単に(a)成分、(b)成分、(c)成分、(d)成分、(e)成分等と称することがある。
本実施形態で用いられる少なくとも2つのエチレン性不飽和基を有する化合物は、好ましくは、少なくとも2つの(メタ)アクリロイル基を有する化合物である。少なくとも2つのエチレン性不飽和基を有する化合物としては、脂環式骨格を有する多官能(メタ)アクリル単量体、脂肪族骨格を有する多官能(メタ)アクリル単量体、ジオキサングリコール骨格を有する多官能(メタ)アクリル単量体、官能基を有する多官能(メタ)アクリル単量体等が挙げられる。なお、ここでの「多官能」とは、エチレン性不飽和基についていうものであり、化合物中に少なくとも2以上のエチレン性不飽和基を有することを意味する。
本実施形態に係る(b)熱重合開始剤としては、t−ヘキシルパーオキシピバレート(パーヘキシルPV、商品名;1時間半減期温度71.3℃、10時間半減期温度53.2℃)、ジラウロイルパーオキサイド(パーヘキシルL、商品名;1時間半減期温度79.3℃、10時間半減期温度61.6℃)、ジ(3,5,5−トリメチルヘキサノイル)パーオキサイド(パーロイル355、商品名;1時間半減期温度76.8℃、10時間半減期温度59.4℃)、1,1,3,3−テトラメチルブチルパーオキシ−2−エチルヘキサノアート(パーオクタO、商品名;1時間半減期温度84.4℃、10時間半減期温度65.3℃)、t−ブチルパーオキシ−2−エチルヘキサノアート(パーブチルO、商品名;1時間半減期温度92.1℃、10時間半減期温度72.1℃)、ベンゾイルパーオキサイド+水(ナイパーBW、商品名;1時間半減期温度92.0℃、10時間半減期温度73.6℃)、1,1−ジ(t−ヘキシルパーオキシ)−3,3,5−トリメチルシクロヘキサン(パーヘキサTMH、商品名;1時間半減期温度106.4℃、10時間半減期温度86.7℃)、1,1−ジ(t−ヘキシルパーオキシ)シクロヘキサン(パーヘキサHC、商品名;1時間半減期温度107.3℃、10時間半減期温度87.1℃)、t−ヘキシルパーオキシイソプロピルモノカルボネート(パーヘキシルI、商品名;1時間半減期温度114.6℃、10時間半減期温度95.0℃)、t−ブチルパーオキシイソプロピルモノカルボネート(パーブチルI、商品名;1時間半減期温度118.4℃、10時間半減期温度98.7℃)、ジクミルパーオキサイド(パークミルD、商品名;1時間半減期温度135.7℃、10時間半減期温度116.4℃)、n−ブチル4,4−ビス(t−ブチルパーオキシ)バレレート(パーヘキサV、商品名;1時間半減期温度126.5℃、10時間半減期温度104.5℃)等の有機過酸化物、2,2’−アゾビスイソブチロニトリル、1,1’−(シクロヘキサン−1,1−カルボニトリル)−2,2’−アゾビス(2−シクロプロピルプロピオニトリル)、2,2’−アゾビス(2,4−ジメチルバレロニトリル)等のアゾ化合物などが挙げられる。これらは、1種を単独で又は2種以上を組み合わせて使用することができる。
dx/dt=k(a−x)・・・(1)
ln{a/(a−x)}=kt・・・(2)
半減期は分解により有機過酸化物濃度が初期の半分に減ずるまでの時間であるから、半減期をt1/2で示し式(2)のxにa/2を代入すれば、下記式(3)のようになる。
kt1/2=ln2・・・(3)
したがって、ある一定温度で熱分解させ、時間(t)とln{a/(a−x)}の関係をプロットし、得られた直線の傾きからkを求めることで、式(3)からその温度における半減期(t1/2)を求めることができる。
lnk=lnA−ΔE/RT ・・・(4)
式(3)及び式(4)よりkを消去すると、
ln(t1/2)=ΔE/RT−ln(A/2)・・・(5)
で表されるので、数点の温度についてt1/2を求め、ln(t1/2)と1/Tの関係をプロットし得られた直線からt1/2=1hにおける温度(1時間半減期温度)が求められる。10時間半減期温度も、t1/2=10hとした場合の温度を求めることで得られる。
本実施形態に係る(c)ヒンダートフェノール系化合物は、分子中にフェノール性水酸基を有し、熱が起因となり樹脂中に発生した過酸化ラジカル(ROO・)を捕捉する能力を有する化合物である。ヒンダートフェノール系化合物としては、上記作用をもたらすものであれば特に限定はされないが、2,6−ジ−t−ブチル−4−メチルフェノール、n−オクタデシル−3−(3’,5’−ジ−t−ブチル−4’−ヒドロキシフェニル)プロピオネート、テトラキス[メチレン−3−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート]メタン、1,3,5−トリス(3,5−ジ−t−ブチル−4−ヒドロキシベンジル)−1,3,5−トリアジン−2,4,6(1H,3H,5H)−トリオン、4,4’,4’’−(1−メチルプロパニル−3−インデン)トリス(6−t−ブチル−m−クレゾール)、3,9−ビス{2−[3−(3−t−ブチル−4−ヒドロキシ−5−メチルフェニル)プロピオニルオキシ]−1,1−ジメチルエチル}−2,4,8,10−テトラオキサスピロ[5.5]ウンデカン及びトリエチレングリコール−ビス[3−(3−t−ブチル−4−ヒドロキシ−5−メチルフェニル)プロピオネート]が挙げられる。これらは1種を単独で又は2種以上を組み合わせて使用することができる。
本実施形態に係る(d)チオエーテル系化合物は、分子内にチオエーテル結合を有する化合物であり、好ましくは下記一般式(17)で表される化合物である。
本実施形態に係る(e)チオール基を有する化合物は、沸点が250℃以上の化合物であることが好ましい。また、熱により樹脂中に生じる共役系に付加反応しその共役構造を切断する作用を有する化合物であることが好ましく、特に、キノンを分解できる塩基性を示さない水素供与体であることがより好ましい。また、チオール基を3つ以上有する化合物であることが好ましい。
本実施形態に係る接着剤組成物は、(a)成分、(b)成分、(c)成分、(d)成分及び(e)成分以外に、必要に応じて後述の任意成分を、有機溶媒に溶解又は分散してワニス状とすることができる。これにより、基材への塗布性を向上させ、作業性を良好にすることができる。
本実施形態に係る接着剤組成物には、カップリング剤を添加することができる。用いられるカップリング剤としては特に制限はなく、シランカップリング剤、チタネート系カップリング剤、アルミニウム系カップリング剤、ジルコネート系カップリング剤、ジルコアルミネート系カップリング剤等の各種のものが用いられる。
本実施形態に係る接着剤組成物には、更に必要に応じて充填剤を含有してもよい。充填剤の種類としては、無機フィラー、有機フィラー等が挙げられるが、耐熱性若しくは熱伝導性を向上させる、又は溶融粘度の調整若しくはチキソトロピック性を付与する観点から、無機フィラーが好ましい。
本実施形態に係る接着剤組成物には、更に必要に応じてバインダー樹脂を含有してもよい。バインダー樹脂としては、アクリル重合体、エポキシ樹脂、ウレタン樹脂、ポリイミド樹脂等が挙げられる。透明性を向上させる観点から、バインダー樹脂はアクリル重合体が好ましく、(f)重量平均分子量が10万以上であるアクリル重合体がより好ましい。
上記官能基は、ワニス状態でのゲル化、使用時のノズル等のつまり、スピンコート時のピンポール発生などの問題を回避する観点から、アミノ基、アミド基、リン酸基、シアノ基、マレイミド基及びエポキシ基からなる群より選ばれる少なくとも1種であることが好ましい。また、上記官能基は、着色をより高度に防止する観点からは、カルボキシル基、酸無水物基、水酸基、リン酸基及びエポキシ基からなる群より選ばれる少なくとも1種であることが好ましい。さらに、これら両方の観点から、上記官能基は、リン酸基又はエポキシ基であることがより好ましく、エポキシ基であることが更に好ましい。
本実施形態に係る半導体装置の製造方法は、半導体基板上に本実施形態に係る接着剤組成物からなる接着剤層(以下、「接着樹脂層」ともいう)を形成する工程(接着剤層形成工程)と、接着剤層を半導体基板と透明基板とで挟み、該半導体基板及び該透明基板を圧着する工程(圧着工程)と、接着剤層を硬化する工程(硬化工程)と、を備える。
接着剤層形成工程としては、本実施形態に係る接着剤組成物を半導体基板上に塗布する方法、又はフィルム状の接着剤組成物を半導体基板に貼り付ける方法を採用することができる。半導体基板は、半導体ウェハ及び半導体素子(半導体チップ)のいずれであってもよい。
接着剤組成物を塗布する方法としては、ディスペンス法、スピンコート法、ダイコート法、ナイフコート法等の手法が挙げられるが、特に高分子量の化合物を含有する組成物の塗布に適しているスピンコート法又はダイコート法が好ましい。
フィルム状の接着剤組成物を貼り付ける方法を採用する場合、充分な濡れ広がりを確保するため、0〜90℃の範囲でラミネートすることが好ましい。また、均一に貼り付けるため、ロールラミネートすることが好ましい。
フィルム状接着剤組成物の製造方法を以下に説明する。本実施形態に係る接着剤組成物を、支持フィルム上に均一に塗布し、使用した溶媒が充分に揮散する条件、例えば、60〜200℃の温度で0.1〜30分間加熱することにより、フィルム状の接着剤組成物を形成する。このとき、フィルム状の接着剤組成物が所望の厚さとなるように、接着剤組成物の溶媒量、粘度、塗布初期の厚さ(ダイコーター、コンマコーター等のコーターを用いる場合は、コーターと支持フィルムのギャップを調整する)、乾燥温度、風量等を調整する。
支持フィルムは、平坦性を有することが好ましい。例えば、PETフィルムのような支持フィルムは静電気による密着が高いため、作業性を向上するために平滑剤を使用している場合がある。平滑剤の種類及び温度によっては、接着剤に微妙な凹凸を転写し平坦性を下げる場合がある。したがって、平滑剤を使用していない支持フィルム又は平滑剤の少ない支持フィルムを使用することが好ましい。また、ポリエチレンフィルム等の支持フィルムは柔軟性に優れる点で好ましいが、ラミネート時にロール痕等が感光性接着剤層表面に転写しないよう、支持フィルムの厚さ及び密度を適宜選択することが好ましい。
続いて、半導体基板上に形成された接着剤層を所望により加熱乾燥する。乾燥する温度には、特に制限はないが、溶媒に溶解又は分散してワニス状とした場合には、使用した溶媒の沸点よりも10〜50℃低くすることが、乾燥時に溶媒の発泡による気泡を作らない意味で好ましい。このような理由で、使用した溶媒の沸点よりも15〜45℃低くすることがより好ましく、使用した溶媒の沸点よりも20〜40℃低くすることが更に好ましい。
なお、上記加熱乾燥は、接着剤層形成工程においてフィルム状の接着剤組成物を貼り付ける方法を採用した場合には、省略することができる。
接着剤層を介して半導体基板と透明基板とを圧着した後、接着剤層を硬化させる。硬化方法は、熱により硬化させる方法が好ましい。
以上の組成を有する本実施形態に係る接着剤層の硬化物のTgは、好ましくは−10℃以上、より好ましくは0℃以上である。
本実施形態に係る光学部品は、上述の接着剤組成物を用いたノンキャビティ構造を有するものである。以下、本実施形態に係る光学部品の一例として、固体撮像素子の裏面照射型構造について、場合により図面を参照しながら説明する。
なお、図8においては、フィルム状接着剤組成物34を予めガラス基板32上に貼り付ける方法について説明したが、支持フィルム36上に形成されたフィルム状接着剤組成物34を、センサ44が搭載された基板42に圧着した後に、支持フィルム36を剥がして、ガラス基板32を圧着してもよい。
また、本実施形態に係る接着剤組成物は硬化後も高い透明性、気密性及び高屈折率を有するため、接着剤としての機能に加えて、ガラス基板の機能を併せ持ち得る。このため、図9に示すように、ガラス基板で封止されていない固体撮像素子とすることもできる(図16参照)。
さらに、図10に示すように、ガラス基板32が積層されたフィルム状接着剤組成物34を、支持台40上で予め個片化し、個片化されたフィルム状接着剤組成物34をセンサ44上にラミネートする方法をとってもよい。
なお、接着剤組成物を塗布する際には、図13の場合と同様に、外周部に、接着剤組成物34を基板42上に留めるための堰46を設けてもよい。
なお、図14及び図15では、液状の接着剤組成物を用いる方法について説明したが、上記と同様にフィルム状接着剤組成物を用いることもできる。
(f−1)
アクリル酸トリシクロ[5.2.1.02,6]デカ−8−イル(FA−513A、日立化成株式会社、商品名)300g、アクリル酸ブチル(BA)350g、メタクリル酸ブチル(BMA)300g、メタクリル酸グリシジル(GMA)50g及びメタクリル酸2−エチルヘキシル(2EHMA)50gを混合し、得られた単量体混合物に更にラウロイルパーオキサイド5g及び連鎖移動剤としてn−オクチルメルカプタン0.45gを溶解させて、混合液とした。
撹拌機及びコンデンサを備えた5Lのオートクレーブに懸濁剤としてポリビニルアルコール0.44g及びイオン交換水2000gを加えた。更に撹拌しながら上記混合液を加え、撹拌回転数250min−1、窒素雰囲気下において60℃で5時間、次いで90℃で2時間重合させ、樹脂粒子を得た(重合率は、質量法で99%であった。)。この樹脂粒子を水洗、脱水及び乾燥することによりアクリル重合体(f−1)を得た。得られた(f−1)の重量平均分子量はMw=48万であった。
メタクリル酸グリシジル2.4質量%、メタクリル酸メチル43.5質量%、アクリル酸エチル18.3質量%及びアクリル酸ブチル35.8質量%を単量体基準で混合した以外は(f−1)と同様の方法によって、重量平均分子量Mw=37万であるアクリル重合体(f−2)を得た。
単量体混合物にアクリロニトリル(AN)1質量%を追加した以外は、(f−1)と同様の方法によって、アクリル重合体(f−3)を得た。得られた(f−3)の重量平均分子量はMw=42万であった。
単量体混合物にアクリロニトリル(AN)2質量%を追加した以外は、(f−1)と同様の方法によって、アクリル重合体(f−4)を得た。得られた(f−4)の重量平均分子量はMw=39万であった。
単量体混合物にアクリロニトリル(AN)3質量%を追加した以外は、(f−1)と同様の方法によって、アクリル重合体(f−5)を得た。得られた(f−5)の重量平均分子量はMw=38万であった。
メタクリル酸グリシジル2.4質量%、メタクリル酸メチル43.5質量%、アクリル酸エチル18.3質量%及びアクリル酸ブチル35.8質量%を単量体基準で混合した以外は(f−1)と同様の方法によって、重量平均分子量Mw=5万であるアクリル重合体(f’−6)を得た。
撹拌機、還流冷却機、不活性ガス導入口及び温度計を備えた500mLフラスコに、酢酸エチル207g、メタクリル酸メチル33.5g、メタクリル酸(MA)1.5g、メタクリル酸ブチル(BMA)24.5g、アクリル酸ブチル(BA)3g、メタクリル酸2−エチルヘキシル(2EHMA)7.5g及びベンジルアクリレート(BzMA)30gを仕込み、窒素ガス雰囲気下で75℃まで昇温した。フラスコ温度を75℃に保ちつつ、2,2’−アゾビス(2,4−ジメチルバレロニトリル)(ADVN)0.7gを滴下し、6時間加熱撹拌した。その後、室温まで冷却し、アクリル重合体(f’−7)を得た。得られた(f’−7)の重量平均分子量はMw=6.2万であった。
ポンプ:L6000 Pump(株式会社日立製作所)
検出器:L3300 RI Monitor(株式会社日立製作所)
カラム:Gelpack GL−S300MDT−5(計2本)(株式会社日立ハイテクノロジーズ、商品名)
カラムサイズ:直径8mm×300mm
溶離液:DMF/THF(質量比1/1)+LiBr・H2O 0.03mol/l+H3PO4 0.06mol/l
試料濃度:0.1質量%
流量:1ml/min
測定温度:40℃
得られたアクリル重合体を、4.0cm×5.0cm×120〜170(実測140〜160μm)μmのガラス基板(MATSUNAMI MICRO COVER GLASS 40mm×50mm THICKNESS No.1;松浪硝子工業株式会社、商品名)上にスピンコーターを用いて均一に塗布し、100℃のホットプレートで5分間乾燥し、乾燥後の膜厚20μmの接着剤層を形成し、試験基板を作製した。この接着剤層を形成した試験基板について、分光光度計U−3310(株式会社日立製作所、商品名;開始800nm、終了200nm、スキャンスピード600nm/min、サンプリング間隔1.0nm)を用いて波長300〜800nmの範囲で透過率を測定した。下記の基準に基づいて初期透過率を評価した。
A:波長400nmにおける透過率が97%以上。
B:波長400nmにおける透過率が97%未満。
上述の初期透過率で使用した試験基板を245℃のホットプレート上に5分間静置した。静置中の樹脂のうねり、クラック、白濁、アウトガス、表面荒れ、色の変化等を目視にて観察した。また透過率の測定を実施した。
上述の初期透過率と同様の方法で作製した試験基板の接着剤層に、90℃でリールラミネータを使用して4.0cm×5.0cm×120〜170(実測140〜160μm)μmのガラス基板(MATSUNAMI MICRO COVER GLASS 40mm×50mm THICKNESS No.1;松浪硝子工業株式会社、商品名)を貼付し、ガラス基板/接着剤層/ガラス基板の3層構造の試験基板を得た。得られた試験基板を245℃のホットプレート上に5分間静置した。静置中、ガラス基材と樹脂が剥離するか観察し、下記の基準に基づいて熱時接着性を評価した。
A:剥離が観察されなかった。
B:剥離が観察された。
(f)成分のTgは、JIS K6240(原料ゴム−示唆走査熱量測定(DSC)によるガラス転移温度の求め方)に準じた方法で測定した。
・UN−952(根上工業株式会社、商品名;ウレタンアクリレートオリゴマー、官能基数:10、Mw=6500〜11000)
・BPE−100(新中村化学工業株式会社、商品名;エチレンオキサイド変性ビスフェノールA型ジメタクリレート)
・BPE-500(新中村化学工業株式会社、商品名;エチレンオキサイド変性ビスフェノールA型ジメタクリレート)
・PE-3A(共栄社化学株式会社、商品名;ペンタエリスリトールトリアクリレート)
・A−DCP(新中村化学工業株式会社、商品名;トリシクロデカンジメタノールジアクリレート)
・FA−P240A(日立化成株式会社、商品名;ポリプロピレングリコールジアクリレート)
・FA−270A(日立化成株式会社、商品名;ポリエチレングリコールジアクリレート)
・A−DOG(新中村化学工業株式会社、商品名;ジオキサングリコールジアクリレート)
・A−9300(新中村化学工業株式会社、商品名;エチレンオキサイド変性イソシアヌル酸トリアクリレート)
・BAH−100Y(新中村化学工業株式会社、商品名;エポキシアクリレート(単官能アクリレート))
・LA(共栄社化学株式会社、商品名;ラウリルアクリレート(単官能アクリレート))
・A−LEN−10(新中村化学工業株式会社、商品名;エチレンオキサイド変性o−フェニルフェノールアクリレート(単官能アクリレート))
・EHPE3150(株式会社ダイセル、商品名;脂環式エポキシ樹脂)
・パークミルD(日油株式会社、商品名;ジクミルパーオキサイド、1時間半減期温度135.7℃、10時間半減期温度116.4℃)
・AO−80(株式会社ADEKA、商品名;ヒンダードフェノール系酸化防止剤、ビス[3−(3−tert−ブチル−4−ヒドロキシ−5−メチルフェニル)プロピオン酸](2,4,8,10−テトラオキサスピロ[5.5]ウンデカン−3,9−ジイル)ビス(2,2−ジメチル−2,1−エタンジイル))
・AO−60(株式会社ADEKA、商品名;ヒンダードフェノール系酸化防止剤、テトラキス[3−(3’、5’−ジ−t−ブチル4’−ヒドロキシフェニル)プロピオン酸]ペンタエリスリトール)
・AO−503(株式会社ADEKA、商品名;チオエーテル系酸化防止剤、3,3−チオビスプロピオン酸ジトリデシル)
・AO−412S(株式会社ADEKA、商品名;チオエーテル系酸化防止剤、ビス[3−(ドデシルチオ)プロピオン酸]2,2−ビス[[3−(ドデシルチオ)−1−オキソプロピルオキシ]メチル]−1,3−プロパンジイル)
・カレンズ MT NR1(昭和電工株式会社、商品名;1,3,5−トリス(3−メルカプトブチリルオキシエチル)−1,3,5−トリアジン−2,4,6(1H,3H,5H)−トリオン)
(f)成分の比較としては、上述の方法で合成した(f−1)〜(f’−7)及びポリメチルメタクリレート(PMMA)を用いた。
・KBM−503(信越化学工業株式会社、商品名;シランカップリング剤、メタクリル酸3−(トリメトキシシリル)プロピル)
・AY43−001(東レ・ダウコーニング株式会社、商品名;シランカップリング剤)
・1B2PZ(四国化成工業株式会社、商品名;1−ベンジル−2−フェニルイミダゾール)
・I−819(BASF社、商品名;ビス(2,4,6−トリメチルベンゾイル)−フェニルフォスフィンオキサイド)
・I−184(BASF社、商品名;1−ヒドロキシ−シクロヘキシルフェニルケトン)
・DMAc(関東化学株式会社、化学物質名;ジメチルアセトアミド)
・シクロヘキサノン(関東化学株式会社、化学物質名)
・MEK(関東化学株式会社、化学物質名;メチルエチルケトン)
得られた実施例及び比較例の接着剤組成物の溶液を、4.0cm×5.0cm×120〜170(実測140〜160μm)μmのガラス基板(MATSUNAMI MICRO COVER GLASS 40mm×50mm THICKNESS No.1;松浪硝子工業株式会社、商品名)上にスピンコーターを用いて均一に塗布し、100℃のホットプレートで5分間乾燥し、乾燥後の膜厚20μmの接着剤層を形成した。比較例2、3、4及び10以外は、この接着剤層を形成したガラス基材を更に150℃で2時間オーブンで硬化し試験基板を作製した。なお、(b)成分に代えて光重合開始剤を用いた比較例2、3、4及び10では、5000mJ/cm2の露光量を照射して光硬化し、試験基板を作製した。この試験基板について、分光光度計U−3310(株式会社日立製作所、商品名;開始800nm、終了200nm、スキャンスピード600nm/min、サンプリング間隔1.0nm)を用いて800〜300nmの範囲で透過率を測定した。
上述の硬化後透過率の測定で使用した試験基板を265℃のホットプレート上に15分間静置した。その後、分光光度計U−3310(株式会社日立製作所、商品名;開始800nm、終了200nm、スキャンスピード600nm/min、サンプリング間隔1.0nm)を用いて波長800〜300nmの範囲で透過率を測定した。
上述の硬化後透過率と同様の方法で、接着樹脂層を形成したガラス基材を得た。このガラス基材の接着樹脂層に、4.0cm×5.0cm×120〜170(実測140〜160μm)μmのガラス基板(MATSUNAMI MICRO COVER GLASS 40mm×50mm THICKNESS No.1;松浪硝子工業株式会社、商品名)を貼り付け、ガラス基板/接着剤層/ガラス基板の3層構造の試験基板を得た。比較例2、3、4及び10以外の試験基板については、150℃で2時間加熱して硬化させた。比較例2、3、4及び10の試験基板は、5000mJ/cm2の露光量を照射して光硬化させた。これらの試験基板を、260℃の熱板上で15分間放置した後、室温(25℃)に戻して5分間保持する操作を行い、試験基板の外観を目視にて観察し、下記の基準に基づいて耐リフロー剥離性を評価した。
A:外観異常が見られなかった。
B:基板の一部に剥離が見られた。
C:基板全面に剥離が見られた。
実施例及び比較例の接着剤組成物の溶液を、離型処理したPETフィルム上にナイフコーターを用いて均一に塗布し、115℃で15分間オーブンにて乾燥させ、乾燥後の膜厚25μmの接着剤層を形成した。この接着剤層を4枚貼り合わせて厚さ100μmとしたものを、180℃で2時間オーブンにて硬化させた。硬化物のTg及び25℃における弾性率を粘弾性試験器(RSA−III;ティー・エイ・インスツルメント社、商品名)により測定した。なお、測定は試験モード:引っ張り試験、試験温度:−50℃〜300℃、昇温速度:5℃/分、周波数:1Hz、チャック間距離:20mmの条件にて行った。
下記の基準に基づいて硬化物のTgを評価した。
A:0℃以上。
B:0℃未満。
以下の基準に基づいて硬化物の25℃における弾性率を評価した。
A:10GPa以下、0.01GPa以上。
B:0.01GPa未満。
Claims (8)
- (a)少なくとも2つのエチレン性不飽和基を有する化合物、
(b)熱重合開始剤、
(c)ヒンダードフェノール系化合物、
(d)チオエーテル系化合物、及び、
(e)チオール基を有する化合物、
を含有する接着剤組成物。 - (f)重量平均分子量が10万以上であるアクリル重合体を更に含有する、請求項1に記載の接着剤組成物。
- 前記(f)重量平均分子量が10万以上であるアクリル重合体がエポキシ基を有する構造単位を含む、請求項2に記載の接着剤組成物。
- 前記(a)少なくとも2つのエチレン性不飽和基を有する化合物が(メタ)アクリロイル基を有するウレタン系化合物を含む、請求項1〜3のいずれか一項に記載の接着剤組成物。
- 光学部品用である、請求項1〜4のいずれか一項に記載の接着剤組成物。
- 請求項1〜5のいずれか一項に記載の接着剤組成物から得られる樹脂硬化物。
- 半導体基板上に請求項1〜5のいずれか一項に記載の接着剤組成物からなる接着剤層を形成する工程と、
前記接着剤層を前記半導体基板と透明基板とで挟み、該半導体基板及び該透明基板を圧着する工程と、
接着剤層を硬化する工程と、
を備える、半導体装置の製造方法。 - 上面に受光部が設けられた半導体基板と、
前記半導体基板上に前記受光部を覆うように設けられた接着剤層と、
前記接着剤層によって前記半導体基板に接着された透明基板と、
を備える固体撮像素子であって、
前記接着剤層は、請求項6に記載の樹脂硬化物である、固体撮像素子。
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KR20160114049A (ko) | 2016-10-04 |
WO2015115552A1 (ja) | 2015-08-06 |
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