JP2894565B2 - Adhesive heat-resistant coating agent - Google Patents
Adhesive heat-resistant coating agentInfo
- Publication number
- JP2894565B2 JP2894565B2 JP1065987A JP6598789A JP2894565B2 JP 2894565 B2 JP2894565 B2 JP 2894565B2 JP 1065987 A JP1065987 A JP 1065987A JP 6598789 A JP6598789 A JP 6598789A JP 2894565 B2 JP2894565 B2 JP 2894565B2
- Authority
- JP
- Japan
- Prior art keywords
- coating agent
- resistant coating
- adhesive heat
- formula
- polyamic acid
- 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.)
- Expired - Lifetime
Links
Classifications
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
Landscapes
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Formation Of Insulating Films (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明はアルミニウム、銅、シリコン、シリコン酸化
膜等に対して接着性に優れた接着性耐熱コーテイング剤
に関する。Description: TECHNICAL FIELD The present invention relates to an adhesive heat-resistant coating agent having excellent adhesion to aluminum, copper, silicon, silicon oxide films and the like.
〔従来の技術〕 従来、半導体の保護膜や層間絶縁膜として多種のポリ
イミドコーテンイグが開発、上市されている。例えば、
ジアミノジフエニルエーテル、パラフエニレンジアミン
のような芳香族ジアミンとピロメリツト酸二無水物、ベ
ンゾフエノンテトラカルボン酸二無水物のようなテトラ
カルボン酸二無水物を原料としたポリイミドコーテイン
グ剤がある。これらは従来のシリコン酸化膜や窒化膜と
比較して平坦化が容易であるため素子の多層化を行う場
合の平坦化材として有望視されている。しかし、これら
のポリイミドコーテインイ剤はいずれもシリコン基板や
シリコン酸化膜上に直接塗布し、絶縁膜を形成した場
合、接着力が弱いためにはく離が生じ易い。特に、プロ
セスの途中ではく離が生じた場合、ポリイミド膜の下の
層の腐食や破壊が起きるため製造プロセス上、大きな問
題となる。そのため、基板とコーテイング剤の間に接着
改良剤を用いることが行われているが、コーテイング剤
による絶縁膜形成後、更に電極のスパツタリング、エツ
チング、ホールの形成、洗浄といつたプロセスを行う場
合、接着力不足によるはく離が顕著に現れ、製品の歩留
りが著しく低下する。また、コーテイング膜形成後の加
熱、減圧等によつて、残留する接着改良剤が分解してガ
スを発生する場合がある。[Related Art] Conventionally, various types of polyimide coatings have been developed and marketed as semiconductor protective films and interlayer insulating films. For example,
There are polyimide coating agents made from aromatic diamines such as diaminodiphenyl ether and paraphenylenediamine and tetracarboxylic dianhydrides such as pyromellitic dianhydride and benzophenone tetracarboxylic dianhydride. Since these are easier to flatten than a conventional silicon oxide film or nitride film, they are considered to be promising as a flattening material in the case of multilayering an element. However, when any of these polyimide coating agents is applied directly on a silicon substrate or a silicon oxide film to form an insulating film, peeling is likely to occur due to weak adhesion. In particular, if peeling occurs during the process, a layer under the polyimide film is corroded or broken, which is a serious problem in the manufacturing process. Therefore, the use of an adhesion improver between the substrate and the coating agent is performed, but after forming the insulating film with the coating agent, further performing electrode sputtering, etching, formation of holes, cleaning and the like, Peeling due to insufficient bonding force appears remarkably, and the yield of the product is significantly reduced. Further, the remaining adhesion improver may be decomposed and generate gas by heating, decompression, etc. after the formation of the coating film.
上記の欠点があるため、ポリイミドコーテイング剤の
持つ低コスト、平坦化可能、軽量、大面積への適用可能
といつた多くのメリツトが発揮されず、現状ではその用
途が非常に限定されている。Due to the above-mentioned drawbacks, many advantages such as low cost, flattenability, light weight, and applicability to a large area of the polyimide coating agent are not exhibited, and at present, its use is very limited.
本発明の目的は上記ポリイミドコーテイング剤の接着
性を改善し、電子部品用材料としての適用範囲を広げ、
更には部品全体の信頼性を高めることにある。The purpose of the present invention is to improve the adhesiveness of the polyimide coating agent, expand the range of application as a material for electronic components,
Another object is to improve the reliability of the entire component.
本発明を概説すれば、本発明はアルミニウム、銅およ
び石英ガラスにスピンコートし、その後、加熱キュアし
て接着性耐熱コーティング膜とするための接着性耐熱コ
ーティング剤であって、下記一般式： （式中R1，R2は下記の式： で表される有機基を示す）で表される化学構造単位を有
するポリアミツク酸の有機極性溶液からなることを特徴
とする。In summary, the present invention is an adhesive heat-resistant coating agent for spin-coating aluminum, copper, and quartz glass and then heating and curing to form an adhesive heat-resistant coating film, having the following general formula: (Where R 1 and R 2 are the following formulas: The organic polar solution of polyamic acid having a chemical structural unit represented by the following formula:
本発明者らは合成実験を行った結果、本発明の接着性
耐熱コーテイング剤が前述のポリイミドコーテイング剤
よりもシリコン、石英ガラス、銅、アルミニウムに対し
て、極めて大きな接着性を有する事実を発見した。本発
明の接着性耐熱コーテイング剤には、式Ｉ以外のもの、
更に常用の助剤が配合されていてもよい。そのような例
の１つに下記一般式II: 〔式中R3は下記の式： で表される基からなる群より選ばれた有機基、R4は下記
の式： で表される基からなる群より選ばれた有機基を示す。但
し、式IIは式Ｉと同一の構造の組合せとなる場合を除
く〕で表される化学構造単位を有するポリアミツク酸が
ある。The present inventors have conducted a synthetic experiment and found that the adhesive heat-resistant coating agent of the present invention has much higher adhesiveness to silicon, quartz glass, copper and aluminum than the above-mentioned polyimide coating agent. . The adhesive heat resistant coatings of the present invention include those other than Formula I,
Further, conventional auxiliaries may be blended. One such example is the following general formula II: [Wherein R 3 is the following formula: R 4 is an organic group selected from the group consisting of groups represented by the following formulas: Represents an organic group selected from the group consisting of groups represented by However, Formula II has the same structural combination as that of Formula I], but there is a polyamic acid having a chemical structural unit represented by the following formula:
本発明者らはこのように式IIで表される化合物をブレ
ンドすることにより、多種多様の接着性耐熱コーテイン
グ剤が提供可能である事実を発見した。The present inventors have discovered that a wide variety of adhesive heat-resistant coating agents can be provided by blending the compound represented by Formula II in this way.
本発明で使用する有機極性溶媒の例にはジメチルホル
ムアミド、N,N−ジメチルアセトアミド、Ｎ−メチル−
２−ピロリドン等を挙げることができる。Examples of the organic polar solvent used in the present invention include dimethylformamide, N, N-dimethylacetamide, N-methyl-
2-pyrrolidone and the like can be mentioned.
本発明の接着性耐熱コーテイング剤の使用方法として
は通常のキヤスト法、スピンコーテイング法等を適用す
ることができ、これを350℃まで加熱キユアすることに
より、接着性に優れたポリイミド膜を形成できる。その
ため、ポリイミド膜形成後、更に熱処理、化学処理等を
行つてもはく離が生じにくいため、製品の歩留り、及び
素子の信頼性を確保できる。また、シリコン、シリコン
酸化膜に対して従来必要であつた接着改良剤を用いるこ
となく接着性を確保できる。その結果、コーテイング膜
形成後に接着改良剤を分解等によるガスの発生が全くな
くなるばかりでなく、接着改良剤の塗布による余分のプ
ロセスが省略できるため低コストが実現できる。As a method of using the adhesive heat-resistant coating agent of the present invention, a normal casting method, a spin coating method, or the like can be applied.By heating this to 350 ° C., a polyimide film having excellent adhesiveness can be formed. . Therefore, peeling is unlikely to occur even if heat treatment, chemical treatment, or the like is further performed after the polyimide film is formed, so that product yield and device reliability can be ensured. In addition, it is possible to secure the adhesiveness to silicon and a silicon oxide film without using a conventionally required adhesion improving agent. As a result, generation of gas due to decomposition of the adhesion improving agent after the formation of the coating film is completely eliminated, and an extra process by applying the adhesion improving agent can be omitted, so that low cost can be realized.
本発明の接着性耐熱コーテイング剤は基板との密着性
に優れるため、エツチング用マスクとしての有用性も高
い。ドライエツチングに適用する場合には従来のフオト
レジストと比較して耐熱性に優れるため、より過酷な条
件での処理が可能である。特に、高出力RFプラズマを用
いた場合にはレジストの焼け付き等の変質がないため、
短時間のエツチングが可能となる。また、ウエツトエツ
チングに適用する場合には、フツ化水素酸等の強酸に対
して安定であるなど、エツチング液の選択範囲が広が
る。Since the adhesive heat-resistant coating agent of the present invention is excellent in adhesion to a substrate, it is also highly useful as a mask for etching. When applied to dry etching, it is superior in heat resistance as compared with conventional photoresists, so that processing under more severe conditions is possible. In particular, when high-power RF plasma is used, there is no deterioration such as burn-in of the resist,
Short-time etching becomes possible. In addition, when the present invention is applied to wet etching, the selection range of the etching liquid is widened, for example, it is stable against a strong acid such as hydrofluoric acid.
更に、界面の接着力が高いため、エツチング液が界面
に進入して起こるオーバーハングやはく離が生じにく
い。Furthermore, since the interface has a high adhesive strength, overhang or peeling that occurs when the etching liquid enters the interface is less likely to occur.
上記用途以外に本発明の接着性耐熱コーテイング剤は
耐熱性接着剤としての用途にも使用できる。この場合、
接着性耐熱コーテイング剤は接着部に塗布して220℃で
プリベークを行つた後、接着部を圧着して350℃まで徐
々に加熱することで硬化する。In addition to the above-mentioned uses, the adhesive heat-resistant coating agent of the present invention can be used also as a heat-resistant adhesive. in this case,
The adhesive heat-resistant coating agent is applied to the bonded portion and prebaked at 220 ° C., and then the bonded portion is pressed and hardened by gradually heating to 350 ° C.
以下、実施例により本発明を具体的に説明するが、本
発明はこれら実施例に限定されるものではない。Hereinafter, the present invention will be described specifically with reference to Examples, but the present invention is not limited to these Examples.
実施例１ 乾燥窒素雰囲気中で500mlのナスフラスコにジアミノ
ジフエニルエーテル20.024g（0.1000モル）を入れ、N,N
−ジメチルアセトアミド258gを加えて溶解した。この溶
液に、2,2−ビス（3,4−ジカルボキシフエニル）ヘキサ
フルオロプロパン二無水物44.422g（0.1000モル）を加
えて、乾燥窒素雰囲気中で24時間かくはんし、ポリアミ
ツク酸の20％N,N−ジメチルアセトアミド溶液を得た。
この接着性耐熱コーテイング剤の銅、アルミニウム、シ
リコン酸化膜に対する接着性を評価するためにJIS K 68
50に従い、せん断接着強さ測定試験片を作製した。な
お、接着性耐熱コーテイング剤は試験片の片面に塗布
し、窒素雰囲気中で70℃２時間、160℃１時間プリベー
クを行つた後、試験片を貼合わせ、約2kg/cm2の圧力を
かけたまま、更に窒素雰囲気中で250℃１時間、350℃１
時間、ポストベークを行つた。この試料についてせん断
接着強さの測定を行い、結果を他の例と共に表１に示し
た。Example 1 In a dry nitrogen atmosphere, 20.024 g (0.1000 mol) of diaminodiphenyl ether was placed in a 500 ml eggplant flask, and N, N
-258 g of dimethylacetamide was added and dissolved. To this solution, 44.422 g (0.1000 mol) of 2,2-bis (3,4-dicarboxyphenyl) hexafluoropropane dianhydride was added, and the mixture was stirred in a dry nitrogen atmosphere for 24 hours to give 20% of polyamic acid. An N, N-dimethylacetamide solution was obtained.
In order to evaluate the adhesion of this adhesive heat-resistant coating agent to copper, aluminum and silicon oxide films, JIS K 68
According to No. 50, a test piece for measuring a shear adhesive strength was prepared. The adhesive heat-resistant coating agent was applied to one side of the test piece, pre-baked in a nitrogen atmosphere at 70 ° C for 2 hours and at 160 ° C for 1 hour, and then bonded to the test piece, and a pressure of about 2 kg / cm 2 was applied. As it is, at 350 ° C for 1 hour at 250 ° C for 1 hour in a nitrogen atmosphere
Time, post bake. The shear bond strength of this sample was measured, and the results are shown in Table 1 together with other examples.
実施例２ 乾燥窒素雰囲気中で500mlのナスフラスコにジアミノ
ジフエニルエーテル20.024g（0.1000モル）を入れ、N,N
−ジメチルアセトアミド258gを加えて溶解した。この溶
液に、ピロメリツト酸無水物21.812g（0.1000モル）を
加えて、乾燥窒素雰囲気中で24時間かくはんし、ポリア
ミツク酸の20％N,N−ジメチルアセトアミド溶液を得
た。このポリアミツク酸溶液に実施例１で合成したポリ
アミツク酸溶液を等量加え、乾燥窒素雰囲気中で溶液が
均一になるまでかくはんした。このポリアミツク酸混合
溶液を用いて実施例１と同様にせん断接着強さ測定試験
片を作製し、せん断接着強さの測定を行つた。結果を表
１に示した。Example 2 In a dry nitrogen atmosphere, 20.024 g (0.1000 mol) of diaminodiphenyl ether was placed in a 500 ml eggplant flask, and N, N
-258 g of dimethylacetamide was added and dissolved. To this solution, 21.812 g (0.1000 mol) of pyromellitic anhydride was added and stirred for 24 hours in a dry nitrogen atmosphere to obtain a 20% N, N-dimethylacetamide solution of polyamic acid. To this polyamic acid solution, an equal amount of the polyamic acid solution synthesized in Example 1 was added and stirred in a dry nitrogen atmosphere until the solution became uniform. Using this polyamic acid mixed solution, a test piece for measuring the shear adhesive strength was prepared in the same manner as in Example 1, and the shear adhesive strength was measured. The results are shown in Table 1.
実施例３〜12 実施例２と同様にして、種々のポリアミツク酸の20％
N,N−ジメチルアセトアミド溶液と実施例１で合成した
ポリアミツク酸溶液の混合溶液を得た。このポリアミツ
ク酸混合溶液を用いて実施例１と同様にせん断接着強さ
測定試験片を作製し、せん断接着強さの測定を行つた。
結果を表１に示した。Examples 3 to 12 In the same manner as in Example 2, 20% of various polyamic acids
A mixed solution of the N, N-dimethylacetamide solution and the polyamic acid solution synthesized in Example 1 was obtained. Using this polyamic acid mixed solution, a test piece for measuring the shear adhesive strength was prepared in the same manner as in Example 1, and the shear adhesive strength was measured.
The results are shown in Table 1.
比較例１ 乾燥窒素雰囲気中で500mlのナスフラスコにジアミノ
ジフエニルエーテル20.024g（0.1000モル）を入れ、N,N
−ジメチルアセトアミド258gを加えて溶解した。この溶
液に、ピロメリツト酸無水物21.812g（0.1000モル）を
加えて、乾燥窒素雰囲気中で24時間かくはんし、ポリア
ミツク酸の20％N,N−ジメチルアセトアミド溶液を得
た。このポリアミツク酸溶液を用いて実施例１と同様に
せん断接着強さ測定試験片を作製し、せん断接着強さの
測定を行つた。結果を表１に示した。Comparative Example 1 In a dry nitrogen atmosphere, 20.024 g (0.1000 mol) of diaminodiphenyl ether was put into a 500 ml eggplant flask, and N, N
-258 g of dimethylacetamide was added and dissolved. To this solution, 21.812 g (0.1000 mol) of pyromellitic anhydride was added and stirred for 24 hours in a dry nitrogen atmosphere to obtain a 20% N, N-dimethylacetamide solution of polyamic acid. Using this polyamic acid solution, a test piece for measuring the shear adhesive strength was prepared in the same manner as in Example 1, and the shear adhesive strength was measured. The results are shown in Table 1.
比較例２ 市販されている代表的なポリイミドコーテイング剤で
ある“セミコフアインSP−740"（東レ社製）を用いて実
施例１と同様にせん断接着強さ測定試験片を作製し、せ
ん断接着強さの測定を行つた。結果表１に示した。Comparative Example 2 A test piece for measuring the shear adhesive strength was prepared in the same manner as in Example 1 using "Semicofine SP-740" (manufactured by Toray Industries, Inc.) which is a commercially available typical polyimide coating agent, and the shear adhesive strength was measured. Measurements were taken. The results are shown in Table 1.
これらの結果から、本発明の接着性耐熱コーテイング
剤は従来のポリイミドコーテイング剤と比較してシリコ
ン、石英ガラス、銅、アルミニウムに対する接着性が優
れていることが明かとなった。 From these results, it became clear that the adhesive heat-resistant coating agent of the present invention had better adhesiveness to silicon, quartz glass, copper, and aluminum than the conventional polyimide coating agent.
〔発明の効果〕 以上説明したように、本発明の接着性耐熱コーテイン
グ剤は従来のポリイミドコーテイング剤と比較して石英
ガラス、銅、アルミニウムに対する接着性が優れている
ので、アルミニウム、銅および石英ガラスにスピンコー
トし、その後、加熱キュアして接着性耐熱コーティング
膜とすることが可能となる。[Effects of the Invention] As described above, the adhesive heat-resistant coating agent of the present invention has excellent adhesion to quartz glass, copper, and aluminum as compared with conventional polyimide coating agents. , And then cured by heating to form an adhesive heat-resistant coating film.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭60−49031（ＪＰ，Ａ) 特開 昭60−177659（ＪＰ，Ａ) 特開 昭62−18426（ＪＰ，Ａ) 特開 昭62−66932（ＪＰ，Ａ) 特開 昭62−231937（ＪＰ，Ａ) 特開 昭59−206434（ＪＰ，Ａ) ──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-60-49031 (JP, A) JP-A-60-177659 (JP, A) JP-A-62-18426 (JP, A) JP-A 62-18426 66932 (JP, A) JP-A-62-231937 (JP, A) JP-A-59-206434 (JP, A)
Claims (2)
温度でプリベークし、その後250℃以上好ましくは350℃
の温度で加熱キュアしてLSI用層間絶縁膜及びエッチン
グマスク用接着性耐熱コーティング膜とするための接着
性耐熱コーティング剤であって、 下記一般式I: （式中R1、R2は下記の式： で表される有機基を示す）で表される化学構造のポリア
ミック酸の有機極性溶液からなることを特徴とするLSI
用層間絶縁膜及びエッチングマスク用接着性耐熱コーテ
ィング剤。1. Coating on a substrate, followed by pre-baking at a temperature of 220 ° C. or less, and then 250 ° C. or more, preferably 350 ° C.
An adhesive heat-resistant coating agent for heating and curing at a temperature of an interlayer insulating film for LSI and an adhesive heat-resistant coating film for an etching mask, having the following general formula I: (Where R1 and R2 are the following formulas: An organic polar solution of a polyamic acid having a chemical structure represented by the following formula:
Adhesive heat-resistant coating agent for interlayer insulation film for etching and etching mask.
式II: （式中R3は下記の式： で表される基からなる群より選ばれた有機基、R4は下記
の式： で表される基からなる群より選ばれた有機基を示す。但
し、式IIは式Ｉと同一の構造の組合わせとなる場合を除
く）で表される化学構造のポリアミック酸の少なくとも
一種を含有していることを特徴とする請求項１記載のLS
I用層間絶縁膜及びエッチングマスク用接着性耐熱コー
ティング剤。2. The adhesive heat-resistant coating agent has the following general formula II: (Where R3 is the following formula: R4 is an organic group selected from the group consisting of groups represented by the following formulas: Represents an organic group selected from the group consisting of groups represented by 2. The LS according to claim 1, wherein the compound contains at least one kind of polyamic acid having a chemical structure represented by the formula (2) except that formula II has the same structural combination as formula (I).
Adhesive heat-resistant coating agent for interlayer insulation film for I and etching mask.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1065987A JP2894565B2 (en) | 1989-03-20 | 1989-03-20 | Adhesive heat-resistant coating agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1065987A JP2894565B2 (en) | 1989-03-20 | 1989-03-20 | Adhesive heat-resistant coating agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02247276A JPH02247276A (en) | 1990-10-03 |
| JP2894565B2 true JP2894565B2 (en) | 1999-05-24 |
Family
ID=13302874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1065987A Expired - Lifetime JP2894565B2 (en) | 1989-03-20 | 1989-03-20 | Adhesive heat-resistant coating agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2894565B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011080014A (en) * | 2009-10-09 | 2011-04-21 | Hitachi Chem Co Ltd | Adhesion improver for glass, resin composition, and method for producing laminate of them and glass |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6266932A (en) * | 1985-09-19 | 1987-03-26 | 三菱化学株式会社 | Resin film and manufacture thereof |
| JPS62231937A (en) * | 1986-04-01 | 1987-10-12 | Canon Inc | Liquid crystal element |
-
1989
- 1989-03-20 JP JP1065987A patent/JP2894565B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02247276A (en) | 1990-10-03 |
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