JPH06107905A - Epoxy resin composition for electronic material - Google Patents
Epoxy resin composition for electronic materialInfo
- Publication number
- JPH06107905A JPH06107905A JP28087692A JP28087692A JPH06107905A JP H06107905 A JPH06107905 A JP H06107905A JP 28087692 A JP28087692 A JP 28087692A JP 28087692 A JP28087692 A JP 28087692A JP H06107905 A JPH06107905 A JP H06107905A
- Authority
- JP
- Japan
- Prior art keywords
- indene
- epoxy resin
- resin composition
- weight
- styrene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 32
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 32
- 239000000203 mixture Substances 0.000 title claims abstract description 17
- 239000012776 electronic material Substances 0.000 title claims abstract description 8
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims abstract description 53
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229920005989 resin Polymers 0.000 claims abstract description 15
- 239000011347 resin Substances 0.000 claims abstract description 15
- 239000000178 monomer Substances 0.000 claims abstract description 11
- 239000000470 constituent Substances 0.000 claims abstract description 7
- 150000002989 phenols Chemical class 0.000 claims abstract description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 10
- -1 styrene compound Chemical class 0.000 abstract description 5
- 238000010538 cationic polymerization reaction Methods 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 238000010521 absorption reaction Methods 0.000 description 8
- 239000003607 modifier Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 229920003986 novolac Polymers 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000008393 encapsulating agent Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 230000020169 heat generation Effects 0.000 description 2
- 150000002469 indenes Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 239000007848 Bronsted acid Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000013032 Hydrocarbon resin Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000010692 aromatic oil Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000011335 coal coke Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、半導体封止材、回路基
板等の電子材料用の分野において使用されるエポキシ樹
脂組成物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an epoxy resin composition used in the field of electronic materials such as semiconductor encapsulants and circuit boards.
【０００２】[0002]
【従来の技術】半導体封止材、回路基板等の電子材料用
の分野において使用されるエポキシ樹脂組成物は、エポ
キシ樹脂に硬化剤、硬化促進剤、改質剤、充填材等のい
くつかを配合したものが使用れている。このような用途
においては、吸水率が低いこと、誘電率が低いこと、耐
熱性が優れることなどが要求されている。また、エポキ
シ樹脂に改質剤として石油樹脂を配合することも特開昭
５４−１８０００号公報等により知られている。しかし
ながら、これらの方法では吸水率や誘電率が高いという
エポキシ樹脂の有する欠点を耐熱性（ガラス転移温
度）、寸法安定性（線膨張係数）等の他の物性を犠牲に
せずに改良することはできなかった。近年、半導体は表
面実装化の傾向を強めているが、これに伴って半導体封
止材は対はんだ耐熱性を要求されている。しかし、エポ
キシ樹脂組成物の吸水率が高いとはんだ浸漬時に水分が
膨張、気化してクラック発生の原因となる。また、プリ
ント基板等の回路基板は高周波がかかった場合の発熱が
問題となっているが、これはエポキシ樹脂組成物の誘電
率が高いことが原因となっている。なお、接着剤の分野
ではあるが、エポキシ樹脂系接着剤に改質剤として、変
成した炭化水素樹脂を配合することが知られている（特
開平２−２３５９７７号）。2. Description of the Related Art Epoxy resin compositions used in the field of electronic materials such as semiconductor encapsulants and circuit boards contain some curing agents, curing accelerators, modifiers, fillers, etc. in the epoxy resin. A blended product is used. In such applications, low water absorption, low dielectric constant, and excellent heat resistance are required. It is also known from JP-A-54-18000 to blend a petroleum resin as a modifier with an epoxy resin. However, in these methods, it is not possible to improve the drawbacks of the epoxy resin such as high water absorption and dielectric constant without sacrificing other physical properties such as heat resistance (glass transition temperature) and dimensional stability (coefficient of linear expansion). could not. In recent years, semiconductors are becoming more and more surface-mounted, and semiconductor encapsulating materials are required to have resistance to soldering heat. However, when the water absorption of the epoxy resin composition is high, water expands and vaporizes during immersion of the solder, causing cracks. Further, a circuit board such as a printed circuit board has a problem of heat generation when a high frequency is applied, which is caused by a high dielectric constant of the epoxy resin composition. Although it is in the field of adhesives, it is known to mix a modified hydrocarbon resin as a modifier into an epoxy resin-based adhesive (JP-A-2-235977).
【０００３】[0003]
【発明が解決しようとする課題】本発明は、電子材料用
のエポキシ樹脂組成物に要求される吸水性、誘電率等が
改良されたエポキシ樹脂組成物を提供することを目的と
する。SUMMARY OF THE INVENTION It is an object of the present invention to provide an epoxy resin composition having improved water absorption, dielectric constant and the like required for an epoxy resin composition for electronic materials.
【０００４】[0004]
【課題を解決するための手段】本発明は、インデン類又
はインデン類及びスチレン類を含むモノマ−をカチオン
重合して得られるインデン系樹脂であって、構成モノマ
−単位としてのインデン類／スチレン類の比（重量比）
が１．５以上であるインデン系樹脂を、必須の配合成分
として含有する電子材料用エポキシ樹脂組成物である。SUMMARY OF THE INVENTION The present invention is an indene resin obtained by cationically polymerizing indene or a monomer containing indene and styrene, wherein indene / styrene as a constituent monomer unit. Ratio (weight ratio)
Is an epoxy resin composition for electronic materials, which contains an indene resin having a ratio of 1.5 or more as an essential component.
【０００５】本発明で使用するインデン系樹脂は、構成
モノマ−中のインデン、アルキルインデン等のインデン
類とスチレン、アルキルスチレン等のスチレンの含有量
の比がインデン類／スチレン類（重量比）として１．５
以上であるものであり、好ましくはインデン類の割合が
全体の６０重量％以上、より好ましくは７０重量％以上
の樹脂である。他の構成モノマ−としてはスチレン類、
クマロン類等の芳香族オレフィンやフェノ−ル類などが
ある。スチレン類は軟化点を低下させる作用があり、フ
ェノ−ル類は相溶性を高める作用があるが、多量に含む
と耐熱性等を低下させる。The indene resin used in the present invention has a ratio of the indenes such as indene and alkylindene to the content of styrene such as styrene and alkylstyrene in the constituent monomer as indene / styrene (weight ratio). 1.5
The above is preferable, and the resin in which the proportion of indene is 60% by weight or more, and more preferably 70% by weight or more of the whole is preferable. Other constituent monomers are styrenes,
There are aromatic olefins such as coumarones and phenols. Styrenes have the effect of lowering the softening point, and phenols have the function of increasing the compatibility, but when contained in a large amount, they lower the heat resistance and the like.
【０００６】このインデン系樹脂は、インデン類又はイ
ンデン類とスチレン類等を含むモノマ−をカチオン重合
して得られるものであり、数平均分子量は５００〜２０
００程度、軟化点３０〜１６０℃程度のものである。こ
の樹脂は、インデン類を所定濃度含有する原料油、好ま
しくはコ−ルタ−ル又はコ−クス炉ガス軽油の蒸留で得
られる１３０〜２００℃留分を主とする原料油や、石油
精製、石油分解の際に生産される芳香族油を蒸留してイ
ンデン類を濃縮した原料油を必要により脱硫処理あるい
は成分調整したのち、ルイス酸、ブレンシュテッド酸又
は固体酸を触媒としてカチオン重合することにより得ら
れる。This indene resin is obtained by cationically polymerizing indene or a monomer containing indene and styrene, and has a number average molecular weight of 500 to 20.
The softening point is about 00 and the softening point is about 30 to 160 ° C. This resin is a feedstock oil containing a predetermined concentration of indene, preferably a feedstock oil mainly composed of a 130 to 200 ° C. fraction obtained by distillation of a coal tar or coke oven gas gas oil, petroleum refining, Aromatic oil produced during petroleum decomposition is distilled to concentrate indene, and if necessary, a raw material oil is subjected to desulfurization treatment or component adjustment, followed by cationic polymerization using Lewis acid, Bronsted acid or solid acid as a catalyst. Is obtained by
【０００７】本発明で使用するエポキシ樹脂は特に限定
するものではないが、ｏ−クレゾ−ルノボラック型エポ
キシ樹脂、フェノ−ルノボラック型エポキシ樹脂、ビフ
ェニル型エポキシ樹脂、ビスフェノ−ルＡ型エポキシ樹
脂、ビスフェノ−ルＦ型エポキシ樹脂、ナフタレン型エ
ポキシ樹脂等が挙げられる。その平均分子量は３００〜
４０００、エポキシ当量は１８０〜３５００ｇ／ｅｑの
範囲が好ましい。The epoxy resin used in the present invention is not particularly limited, but o-cresol novolac type epoxy resin, phenol novolac type epoxy resin, biphenyl type epoxy resin, bisphenol A type epoxy resin, bispheno-type epoxy resin. Examples thereof include F-type epoxy resin and naphthalene-type epoxy resin. Its average molecular weight is 300-
4000, and the epoxy equivalent is preferably in the range of 180 to 3500 g / eq.
【０００８】本発明のエポキシ樹脂組成物には硬化剤を
配合する。硬化剤の種類は特に限定するものではない
が、ジシアンジアミド等のポリアミド類、ノボラック型
フェノ−ル樹脂等のポリオ−ル等を挙げることができ
る。配合比率は、エポキシ樹脂１００重量部に対し、イ
ンデン系樹脂３〜５０重量部の範囲が好ましく、硬化剤
はエポキシ樹脂に対し当量比０．８〜１．５の範囲で配
合することが好ましい。更に、その他の配合物として、
シリカ等の充填材、ワックス等の離型材等を配合するこ
とができる。A curing agent is added to the epoxy resin composition of the present invention. The type of the curing agent is not particularly limited, but examples thereof include polyamides such as dicyandiamide and polyols such as novolac type phenol resin. The blending ratio is preferably in the range of 3 to 50 parts by weight of the indene resin with respect to 100 parts by weight of the epoxy resin, and the curing agent is preferably blended in an equivalent ratio of 0.8 to 1.5 with respect to the epoxy resin. Furthermore, as other compounds,
A filler such as silica and a release material such as wax can be mixed.
【０００９】[0009]
【作用】本発明のエポキシ樹脂組成物に使用するインデ
ン系樹脂は、エポキシ樹脂に比べて疎水性であるため、
吸水率や誘電率の低減に効果があり、更に主構成モノマ
−であるインデン類が環状芳香族オレフィンであって、
構造が剛直であるので、ガラス転移温度低下による耐熱
性の劣化等物性の低下が小さいものと考えられる。Since the indene resin used in the epoxy resin composition of the present invention is more hydrophobic than the epoxy resin,
It is effective in reducing the water absorption rate and the dielectric constant, and further, the indene which is a main constituent monomer is a cyclic aromatic olefin,
Since the structure is rigid, it is considered that deterioration of physical properties such as deterioration of heat resistance due to a decrease in glass transition temperature is small.
【００１０】[0010]
【実施例】 実施例１〜４ エポキシ樹脂として、ｏ−クレゾ−ルノボラック型エポ
キシ樹脂（日本化薬（株）製、ＥＯＣＮ−１０２９）、
硬化剤としてノボラック型フェノ−ル樹脂（荒川化学工
業（株）製、タマノル７５８）、硬化促進剤としてトリ
フェニルフォスフィン及び表１に示す改質剤を使用し、
エポキシ樹脂１００重量部、硬化剤５４．６重量部、硬
化促進剤２．０６重量部、改質剤２０重量部の割合で配
合し、ロ−ルで混練し、１５０℃でプレス成形後、１８
０℃で１昼夜エ−ジングを行い、試料を調製した。物性
の測定法は以下のとおりであり、測定結果を表２に示
す。Examples Examples 1 to 4 As an epoxy resin, an o-cresol novolac type epoxy resin (EOCN-1029 manufactured by Nippon Kayaku Co., Ltd.),
A novolac-type phenol resin (Tamanor 758, manufactured by Arakawa Chemical Industry Co., Ltd.) was used as a curing agent, triphenylphosphine was used as a curing accelerator, and a modifier shown in Table 1 was used.
100 parts by weight of an epoxy resin, 54.6 parts by weight of a curing agent, 2.06 parts by weight of a curing accelerator and 20 parts by weight of a modifier are blended, kneaded with a roll and press-molded at 150 ° C.
A sample was prepared by aging for one day at 0 ° C. The methods for measuring physical properties are as follows, and the measurement results are shown in Table 2.
【００１１】＊吸水率 プレッシャ−クッカ−テスタ−を用い、１３３℃、１０
０％ＲＨ、圧力３ａｔｍの雰囲気下、９６ｈｒ後の硬化
組成物の重量増加率を測定した。 ＊誘電率 周波数１００ｋＨｚ、２５℃で硬化物の電気容量を測定
し、誘電率を算出した。 ＊ガラス転移温度（ガラス領域）と線膨張係数 ＴＭＡ法を用いた。昇温速度は１０℃／ｍｉｎとし、線
膨張係数は１００℃での値を求めた。* Water absorption rate Using a pressure cooker tester, 133 ° C, 10
The weight increase rate of the cured composition after 96 hours was measured in an atmosphere of 0% RH and a pressure of 3 atm. * Dielectric constant The dielectric constant was calculated by measuring the electric capacity of the cured product at a frequency of 100 kHz and 25 ° C. * Glass transition temperature (glass region) and linear expansion coefficient TMA method was used. The temperature rising rate was 10 ° C./min, and the linear expansion coefficient was a value at 100 ° C.
【００１２】比較例１〜４ 改質剤を配合しない例、改質剤として表１に示す樹脂Ｓ
１〜Ｓ３を使用した例について、実施例１と同様に試料
を調製し、物性を測定した。結果を表２に示す。実施例
に比べ、吸水率、誘電率が高いか、耐熱性が低かった
り、線膨張係数が高いなどの問題があることが分かる。Comparative Examples 1 to 4 Resins S shown in Table 1 as examples of modifiers containing no modifier.
For the examples using 1 to S3, samples were prepared in the same manner as in Example 1 and the physical properties were measured. The results are shown in Table 2. It can be seen that there are problems such as high water absorption and dielectric constant, low heat resistance, and high linear expansion coefficient, as compared with the examples.
【００１３】[0013]
【表１】 [Table 1]
【００１４】[0014]
【表２】 [Table 2]
【００１５】[0015]
【発明の効果】本発明のエポキシ樹脂組成物は低吸水
率、低誘電率であるにも係わらず、物性値の低下が少な
く、はんだ耐熱性に優れ、発熱の少ない材料となり、電
子材料用エポキシ樹脂組成物として優れた物性を有す
る。INDUSTRIAL APPLICABILITY The epoxy resin composition of the present invention has a low water absorption rate and a low dielectric constant, but exhibits little deterioration in physical properties, excellent solder heat resistance, and little heat generation. It has excellent physical properties as a resin composition.
Claims (2)
類を含むモノマ−をカチオン重合して得られるインデン
系樹脂であって、構成モノマ−単位としてのインデン類
／スチレン類の比（重量比）が１．５以上であるインデ
ン系樹脂を、必須の配合成分として含有することを特徴
とする電子材料用エポキシ樹脂組成物。1. An indene resin obtained by cationically polymerizing indene or a monomer containing indene and styrene, wherein the ratio (weight ratio) of indene / styrene as a constituent monomer unit is 1. An epoxy resin composition for electronic materials, which contains an indene resin having a ratio of 0.5 or more as an essential component.
ノマ−単位として１０重量％以下含む請求項１記載の電
子材料用エポキシ樹脂組成物。2. The epoxy resin composition for electronic materials according to claim 1, wherein the indene resin contains phenols in an amount of 10% by weight or less as a constituent monomer unit.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28087692A JP2849512B2 (en) | 1992-09-25 | 1992-09-25 | Epoxy resin composition for electronic materials |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28087692A JP2849512B2 (en) | 1992-09-25 | 1992-09-25 | Epoxy resin composition for electronic materials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06107905A true JPH06107905A (en) | 1994-04-19 |
| JP2849512B2 JP2849512B2 (en) | 1999-01-20 |
Family
ID=17631186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28087692A Expired - Fee Related JP2849512B2 (en) | 1992-09-25 | 1992-09-25 | Epoxy resin composition for electronic materials |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2849512B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110791052A (en) * | 2019-10-22 | 2020-02-14 | 长兴电子材料（昆山）有限公司 | High-reliability epoxy resin composition and application thereof |
| JP2020105279A (en) * | 2018-12-26 | 2020-07-09 | 住友ベークライト株式会社 | Resin composition, resin film with carrier using the same, prepreg, laminate, printed wiring board and semiconductor device |
| WO2020161926A1 (en) * | 2019-02-05 | 2020-08-13 | 株式会社プリンテック | Resin composition and method for producing same |
-
1992
- 1992-09-25 JP JP28087692A patent/JP2849512B2/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020105279A (en) * | 2018-12-26 | 2020-07-09 | 住友ベークライト株式会社 | Resin composition, resin film with carrier using the same, prepreg, laminate, printed wiring board and semiconductor device |
| WO2020161926A1 (en) * | 2019-02-05 | 2020-08-13 | 株式会社プリンテック | Resin composition and method for producing same |
| CN110791052A (en) * | 2019-10-22 | 2020-02-14 | 长兴电子材料（昆山）有限公司 | High-reliability epoxy resin composition and application thereof |
| CN110791052B (en) * | 2019-10-22 | 2023-07-07 | 昆山兴凯半导体材料有限公司 | High-reliability epoxy resin composition and application thereof |
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