JP2948235B2 - Novolak resin composition for positive photoresist - Google Patents
Novolak resin composition for positive photoresistInfo
- Publication number
- JP2948235B2 JP2948235B2 JP16575389A JP16575389A JP2948235B2 JP 2948235 B2 JP2948235 B2 JP 2948235B2 JP 16575389 A JP16575389 A JP 16575389A JP 16575389 A JP16575389 A JP 16575389A JP 2948235 B2 JP2948235 B2 JP 2948235B2
- Authority
- JP
- Japan
- Prior art keywords
- cresol
- novolak resin
- compound
- meta
- group
- 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
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- Phenolic Resins Or Amino Resins (AREA)
Description
【発明の詳細な説明】 〈産業上の利用分野〉 本発明はポジ型フォトレジスト用ノボラック樹脂組成
物に関し、さらに詳しくは特にパターン形状に優れ、か
つ耐熱性、解像力、感度の良好なポジ型フォトレジスト
用ノボラック樹脂組成物に関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a novolak resin composition for a positive photoresist, and more particularly to a positive photoresist having excellent pattern shape and excellent heat resistance, resolution and sensitivity. The present invention relates to a novolak resin composition for a resist.
〈従来の技術〉 ポジ型フォトレジストはアルカリ可溶性のノボラック
樹脂と、フォトセンシタイザーと呼ばれる光分解成分と
から構成されており、特にIC、LSI等の集積度の高い回
路製作を行う際に使用する写真食刻法におけるエッチン
グ保護膜等として最近利用度が高まってきている。この
集積回路製作については高集積化に伴う微細化が急速に
進行し、今やサブミクロンのパターン形成が要求される
に至っており、今後、更に高集積化にともなってパター
ンの微細化が進むことは必至と考えられている。このよ
うな状況下でパターン形成の良好な、更に耐熱性、解像
力、感度を向上させたポジ型フォトレジストに対する要
求は非常に高いものがある。<Conventional technology> Positive-type photoresists are composed of alkali-soluble novolak resin and photo-decomposition components called photosensitizers, and are used especially when manufacturing highly integrated circuits such as ICs and LSIs. Recently, its use as an etching protective film in a photolithography method has been increasing. With regard to the fabrication of integrated circuits, miniaturization has rapidly progressed due to high integration, and submicron pattern formation is now required. In the future, further miniaturization of patterns will be required with higher integration. It is considered inevitable. Under such circumstances, there is an extremely high demand for a positive photoresist having good pattern formation and further improved heat resistance, resolution and sensitivity.
これらの要求に対応すべく、特開昭62−172341号で
は、溶剤存在下にてフェノール類とアルデヒド類を酸性
触媒で反応させて分子量分布を狭くしたノボラック樹脂
を得ており、これを配合したポジ型フォトレジストのパ
ターン形状性、感度の向上を試みている。To meet these demands, JP-A-62-172341 discloses a novolak resin having a narrow molecular weight distribution by reacting a phenol and an aldehyde with an acidic catalyst in the presence of a solvent. We are trying to improve the pattern shape and sensitivity of positive photoresist.
しかし、これらの方法では樹脂製造に関わる時間が極
端に長くなり作業性が悪くその結果コスト的に高価にな
ってしまうという課題があり、更に、フェノール類の配
合については、メタクレゾール・パラクレゾールの配合
比率或はメタクレゾール・パラクレゾール・キシレノー
ルの配合比率に於てメタククレゾールに対するパラクレ
ゾールの配合、又はメタクレゾールに対するパラクレゾ
ール及びキシレノールの配合を増加させることによりパ
ターン形状を向上させているが、解像力、感度、耐熱性
を共に満足させる上で、解像力及び感度を向上させるた
めには分子量を下げなくてはならずその結果耐熱性の低
下を招く一方、耐熱性を向上させるためには分子量を上
げなくてはならずその結果解像度及び感度の低下を招く
といった欠点があった。However, these methods have the problem that the time involved in resin production becomes extremely long and workability is poor, resulting in high cost.In addition, for the mixing of phenols, meta-cresol and para-cresol The pattern shape is improved by increasing the blending ratio of paracresol to methacresol or the blending ratio of paracresol and xylenol to metacresol in the blending ratio or the blending ratio of meta-cresol-para-cresol-xylenol, In order to satisfy both resolution, sensitivity and heat resistance, it is necessary to lower the molecular weight in order to improve the resolution and sensitivity. Must be increased, resulting in reduced resolution and sensitivity. .
従って、現状のポジ型フォトレジストを見ると、パタ
ーン形状、耐熱性、解像力、感度の点で必ずしも要求を
満たしているとは云えない。Therefore, looking at the current positive photoresist, it cannot be said that the requirements are always satisfied in terms of pattern shape, heat resistance, resolution, and sensitivity.
〈発明が解決しようとする課題〉 本発明は上記要望に応えるべくなされたもので、ポジ
型フォトレジストに於て良好なパターン形状、耐熱性、
解像度、感度を与えるノボラック樹脂組成物を提供する
ことを目的とする。<Problems to be Solved by the Invention> The present invention has been made to meet the above-mentioned demands, and has a good pattern shape, heat resistance,
An object of the present invention is to provide a novolak resin composition that provides resolution and sensitivity.
〈問題点を解決しようとする手段〉 本発明者らは上記目的を達成するため、鋭意検討を重
ねた結果、フェノール類として下記一般式で示される化
合物Ａ及び 下記一般式で示される化合物Ｂを用い、 分子量分布を狭くしパターン形状を向上させ、化合物Ａ
または化合物Ｂとメタクレゾール、又はメタクレゾール
・パラクレゾール混合物を用いることにより解像度、感
度及び耐熱性の両立するポジ型フォトレジスト用ノボラ
ックを得ることを見いだし本発明に到った。<Means for Solving the Problems> The present inventors have conducted intensive studies in order to achieve the above object, and as a result, compounds A and phenol represented by the following general formula as phenols Using a compound B represented by the following general formula, Compound A with narrow molecular weight distribution and improved pattern shape
Alternatively, it has been found that a compound novolak for a positive photoresist having both resolution, sensitivity and heat resistance can be obtained by using compound B and meta-cresol or a mixture of meta-cresol and para-cresol.
すなわち、本発明は下記一般式で示される化合物Ａ又
は 下記一般式で示される化合物Ｂに メタクレゾール又はメタクレゾール・パラクレゾール混
合物を配合し、酸の存在下アルデヒド類と反応させるこ
とにより製造されるノボラック樹脂であって、化合物Ａ
または化合物Ｂとメタクレゾール又はメタクレゾール・
パラクレゾール混合物の配合比が1:10〜1:1の範囲内に
あり、かつ重量平均分子量が3,000〜15,000であること
を特徴とするポジ型フォトレジスト用ノボラック樹脂組
成物である。That is, the present invention provides a compound A represented by the following general formula or Compound B represented by the following general formula A novolak resin produced by blending meta-cresol or a mixture of meta-cresol and para-cresol, and reacting with an aldehyde in the presence of an acid, comprising a compound A
Or compound B and meta-cresol or meta-cresol
A novolak resin composition for a positive photoresist, wherein the compounding ratio of the paracresol mixture is in the range of 1:10 to 1: 1 and the weight average molecular weight is 3,000 to 15,000.
本発明で用いられるフェノール類の内、一般式Ａで示
される化合物、または一般式Ｂで示される化合物におい
て、Ｒはアルキル基、アルコキシ基、アリール基または
アラールキル基である。アルキル基としては分岐鎖状あ
るいは環状炭素数10までのアルキル基、例えばメチル
基、エチル基、イソプロピル基、ブチル基、２−エチル
ヘキシル基、シクロヘキシル基があり、アルコキシ基と
しては炭素数４以下のアルコキシ基、例えばメトキシ
基、エトキシ基、プロポキシ基、ブトキシ基がある。ア
リール基としては例えばフェニル基、トリル基、クミル
基等があり、アラールキル基としては炭素数６〜10のア
ラールキル基例えばベンジル基、フェネチル基等をあげ
ることが出来る。又、アルデヒド類は特に限定しないが
ホルマリン、パラホルムアルデヒド、トリオキサン、テ
トラオキサン等があげられる。Among the phenols used in the present invention, in the compound represented by the general formula A or the compound represented by the general formula B, R is an alkyl group, an alkoxy group, an aryl group or an aralkyl group. Examples of the alkyl group include a branched or cyclic alkyl group having up to 10 carbon atoms, such as a methyl group, an ethyl group, an isopropyl group, a butyl group, a 2-ethylhexyl group, and a cyclohexyl group. There are groups such as methoxy, ethoxy, propoxy, butoxy. Examples of the aryl group include a phenyl group, a tolyl group, and a cumyl group. Examples of the aralkyl group include an aralkyl group having 6 to 10 carbon atoms, such as a benzyl group and a phenethyl group. The aldehydes are not particularly limited, but include formalin, paraformaldehyde, trioxane, tetraoxane and the like.
更に、化合物Ａまたは化合物Ｂとメタクレゾール又は
メタクレゾール・パラクレゾール混合物との重量比1:10
〜1:1の範囲内にあることが好ましく、1:10よりも大き
くなるとこれを用いたフォトレジストのパターン形状の
改善は余り期待できず1:1よりも小さくなると感度が大
幅に低下し、実用的でなくなる。又、メタクレゾール及
びパラクレゾール混合物に於けるメタクレゾールとパラ
クレゾールの配合組成比は10:0〜5:5が好ましく、この
配合組成比よりパラクレゾールが多くなるとフォトレジ
ストの現像性が低下し、実用的でなくなる。Furthermore, the weight ratio of compound A or compound B to meta-cresol or a mixture of meta-cresol and para-cresol 1:10
It is preferable to be in the range of ~ 1: 1, and if it is larger than 1:10, the pattern shape of the photoresist using this cannot be expected to be improved much, and if it is smaller than 1: 1 the sensitivity is greatly reduced, It becomes impractical. Also, the composition ratio of meta-cresol and para-cresol in the mixture of meta-cresol and para-cresol is preferably from 10: 0 to 5: 5. It becomes impractical.
なお、これらを反応させる際、化合物Ａまたは化合物
Ｂをフェノール類、アルデヒド類と共に仕込んで反応さ
せることが望ましいが、化合物Ａまたは化合物Ｂとフェ
ノール類を最初に反応させ、次いでアルデヒド類を添加
して反応しても構わず、その際溶剤を加えて反応しても
差し支えない。When reacting them, it is desirable to react compound A or compound B with phenols and aldehydes, but it is desirable to react compound A or compound B with phenols first, and then add aldehydes. The reaction may be performed, and at that time, the reaction may be performed by adding a solvent.
〈実施例〉 本発明を更に具体的に説明するが、本発明はこれらの
実施例によって何等制約されるものではない。<Examples> The present invention will be described more specifically, but the present invention is not limited by these examples.
実施例１ 内容積500mの三ツ口フラスコにメタクレゾール150
g、化合物A20g、37％ホルマリン100g、エチルセロソル
ブ60gを仕込み、撹拌しながらシュウ酸1gを添加し反応
温度95〜100℃に保ち10時間反応させた。反応後減圧下
にて脱水及び脱溶剤を行い重量平均分子量8,000のノボ
ラック樹脂を得た。Example 1 Metacresol 150 was placed in a three-necked flask having an inner volume of 500 m.
g, Compound A (20 g), 37% formalin (100 g), and ethyl cellosolve (60 g) were charged, and oxalic acid (1 g) was added with stirring, and the mixture was reacted at a reaction temperature of 95 to 100 ° C. for 10 hours. After the reaction, dehydration and solvent removal were performed under reduced pressure to obtain a novolak resin having a weight average molecular weight of 8,000.
実施例２ 実施例１と同様な反応装置にメタクレゾール150g、化
合物B20g、37％ホルマリン105g、エチルセロソルブ60g
を仕込み、撹拌しながらシュウ酸1gを添加し、反応温度
95〜100℃に保ち、10時間反応させた。反応後実施例１
と同様に減圧下で脱水、脱溶剤し重量平均分子量13,500
のノボラック樹脂を得た。Example 2 150 g of meta-cresol, 20 g of compound B, 105 g of 37% formalin, and 60 g of ethyl cellosolve were placed in the same reaction apparatus as in Example 1.
Was added, and 1 g of oxalic acid was added with stirring.
The reaction was maintained at 95-100 ° C for 10 hours. Example 1 after reaction
Dehydration and desolvation under reduced pressure in the same manner as described above, weight average molecular weight 13,500
Novolak resin was obtained.
実施例３ 実施例１と同様な反応装置に混合クレゾール（メタク
レゾール／パラクレゾールの重量比＝6/4）37g、メタク
レゾール110g、化合物A45g、37％ホルマリン80g、エチ
ルセロソルブ60gを仕込み、撹拌しながらシュウ酸1gを
添加し、反応温度95〜100℃に保ち、10時間反応させ
た。反応後、減圧下にて脱水、脱溶剤を行い重量平均分
子量5,000のノボラック樹脂を得た。Example 3 A reaction apparatus similar to that of Example 1 was charged with 37 g of mixed cresol (weight ratio of meta-cresol / para-cresol = 6/4), 110 g of meta-cresol, 45 g of compound A, 80 g of 37% formalin, and 60 g of ethyl cellosolve, and stirred. While adding 1 g of oxalic acid, the mixture was reacted at a reaction temperature of 95 to 100 ° C. for 10 hours. After the reaction, dehydration and solvent removal were performed under reduced pressure to obtain a novolak resin having a weight average molecular weight of 5,000.
実施例４ 実施例１〜３の比較として、実施例１と同様な反応装
置に混合クレゾール（メタクレゾール／パラクレゾール
の重量比＝6/4）150g、37％ホルマリン80g、エチルセロ
ソルブ60gを仕込み、撹拌しながらシュウ酸1gを添加
し、反応温度95〜100℃に保ち、10時間反応させた。反
応後、減圧下にて脱水、脱溶剤を行い重量平均分子量8,
000のノボラック樹脂を得た。Example 4 As a comparison with Examples 1 to 3, 150 g of mixed cresol (weight ratio of meta-cresol / para-cresol = 6/4), 80 g of 37% formalin, and 60 g of ethyl cellosolve were charged into the same reactor as in Example 1. While stirring, 1 g of oxalic acid was added, and the reaction was maintained at a reaction temperature of 95 to 100 ° C. and reacted for 10 hours. After the reaction, dehydration and desolvation were performed under reduced pressure, and the weight average molecular weight was 8,
000 novolak resins were obtained.
実施例１〜４で得られたノボラック樹脂100重量部と
ナフトキノン1,2−ジアジド−５−スルホン酸の2,3,4−
トリヒドロキシベンゾフェノンエステル30重量部とをエ
チレングリコールモノエチルエーテルアセテート390重
量部に溶解し、レジスト液を調合した。これらの各組成
物を0.2μｍのメンブレンフィルターを用い濾過し、レ
ジスト液とした。このレジスト組成物を常法により洗浄
した後シリコンウエハーに1,3μｍ厚に塗布した。100 parts by weight of the novolak resin obtained in Examples 1-4 and 2,3,4-naphthoquinone 1,2-diazide-5-sulfonic acid
30 parts by weight of trihydroxybenzophenone ester and 390 parts by weight of ethylene glycol monoethyl ether acetate were dissolved to prepare a resist solution. Each of these compositions was filtered using a 0.2 μm membrane filter to obtain a resist solution. The resist composition was washed by a conventional method and applied to a silicon wafer to a thickness of 1.3 μm.
次いでこのシリコンウエハーを110℃で90秒間乾燥し
た。その後縮小投影露光装置を用いテストチャートマス
クを介して露光し、現像液NMD−３（東京応化工業製）
を用い30秒間現像した。Next, the silicon wafer was dried at 110 ° C. for 90 seconds. Thereafter, exposure is performed through a test chart mask using a reduction projection exposure apparatus, and a developing solution NMD-3 (manufactured by Tokyo Ohka Kogyo)
For 30 seconds.
現像後のレジストパターンについたシリコンウエハー
を種々の温度に設定したクリーンオーブン中に30秒間放
置し、その後レジストパターンを走査型電子顕微鏡で観
察することによりパターン形状、耐熱性を評価した。The silicon wafer having the developed resist pattern was left in a clean oven set at various temperatures for 30 seconds, and then the resist pattern was observed with a scanning electron microscope to evaluate the pattern shape and heat resistance.
これらの結果をまとめて表１に記した。The results are summarized in Table 1.
〈発明の効果〉 本発明より得られたノボラック樹脂はフォトレジスト
用として適切な分子量を有し、その結果このノボラック
樹脂を使用したポジ型フォトレジストは良好なパターン
形状を有し、かつ感度も良く、耐熱性等の性能面も良好
である。 <Effect of the Invention> The novolak resin obtained from the present invention has an appropriate molecular weight for use as a photoresist, and as a result, a positive photoresist using this novolak resin has a good pattern shape, and has good sensitivity. Also, the performances such as heat resistance are good.
従って、微細な回路パターンを有する集積回路を製作
することが出来る。Therefore, an integrated circuit having a fine circuit pattern can be manufactured.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 木村 陽子 群馬県高崎市大八木町622番地 群栄化 学工業株式会社内 (72)発明者 長谷川 正 群馬県高崎市大八木町622番地 群栄化 学工業株式会社内 (56)参考文献 特開 平２−37348（ＪＰ，Ａ) (58)調査した分野(Int.Cl.6，ＤＢ名) G03F 7/00 - 7/42 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Yoko Kimura 622 Oyagi-cho, Takasaki City, Gunma Prefecture Inside Gunei Kagaku Kogyo Co., Ltd. (56) References JP-A-2-37348 (JP, A) (58) Fields investigated (Int. Cl. 6 , DB name) G03F 7/ 00-7/42
Claims (4)
式中Ｒはアルキル基、アルコキシ基、アリール基または
アラールキル基を示す）と、 メタクレゾールの混合物を酸の存在下でアルデヒド類と
反応させることによって製造されるノボラック樹脂であ
って、上記化合物Ａとメタクレゾールの重量比が1:10〜
1:1の範囲内にあり、かつ上記ノボラック樹脂の重量平
均分子量が3,000〜15,000であることを特徴とするポジ
型フォトレジスト用ノボラック樹脂組成物。(1) a compound A represented by the following general formula (provided that
Wherein R represents an alkyl group, an alkoxy group, an aryl group or an aralkyl group); A novolak resin produced by reacting a mixture of meta-cresol with aldehydes in the presence of an acid, wherein the weight ratio of the compound A to meta-cresol is from 1:10 to
A novolak resin composition for a positive photoresist, wherein the composition is in the range of 1: 1 and the weight average molecular weight of the novolak resin is 3,000 to 15,000.
式中Ｒはアルキル基、アルコキシ基、アリール基または
アラールキル基を示す）と、 メタクレゾールの混合物を酸の存在下でアルデヒド類と
反応させることによって製造されるノボラック樹脂であ
って、上記化合物Ｂとメタクレゾールの重量比が1:10〜
1:1の範囲内にあり、かつ上記ノボラック樹脂の重量平
均分子量が3,000〜15,000であることを特徴とするポジ
型フォトレジスト用ノボラック樹脂組成物。2. A compound B represented by the following general formula (provided that
Wherein R represents an alkyl group, an alkoxy group, an aryl group or an aralkyl group); A novolak resin produced by reacting a mixture of meta-cresol with aldehydes in the presence of an acid, wherein the weight ratio of the compound B to meta-cresol is from 1:10 to
A novolak resin composition for a positive photoresist, wherein the composition is in the range of 1: 1 and the weight average molecular weight of the novolak resin is 3,000 to 15,000.
式中Ｒはアルキル基、アルコキシ基、アリール基または
アラールキル基を示す）と、 メタクレゾール及びパラクレゾールの混合物を酸の存在
下でアルデヒド類と反応させることによって製造される
樹脂であって、上記化合物Ａと、組成重量比が10:0〜5:
5であるメタクレゾール及びパラクレゾール混合物との
重量比が1:10〜1:1の範囲内にあり、かつ上記ノボラッ
ク樹脂の重量平均分子量が3,000〜15,000であることを
特徴とするポジ型フォトレジスト用ノボラック樹脂組成
物。A compound A represented by the following general formula (provided that
Wherein R represents an alkyl group, an alkoxy group, an aryl group or an aralkyl group); A resin produced by reacting a mixture of meta-cresol and para-cresol with an aldehyde in the presence of an acid, wherein the compound A has a composition weight ratio of 10: 0 to 5:
The positive photoresist is characterized in that the weight ratio between the meta-cresol and para-cresol mixture that is 5 is in the range of 1:10 to 1: 1 and the weight-average molecular weight of the novolak resin is 3,000 to 15,000. Novolak resin composition.
式中Ｒはアルキル基、アルコキシ基、アリール基または
アラールキル基を示す）と、 メタクレゾール及びパラクレゾールの混合物を酸の存在
下でアルデヒド類と反応させることによって製造される
ノボラック樹脂であって、上記化合物Ｂと、組成重量比
が10:0〜5:5であるメタクレゾール及びパラクレゾール
混合物との重量比が1:10〜1:1の範囲内でにあり、かつ
上記ノボラック樹脂の重量平均分子量が3,000〜15,000
であることを特徴とするポジ型フォトレジスト用ノボラ
ック樹脂組成物。4. A compound B represented by the following general formula (provided that
Wherein R represents an alkyl group, an alkoxy group, an aryl group or an aralkyl group); A novolak resin produced by reacting a mixture of meta-cresol and para-cresol with an aldehyde in the presence of an acid, wherein the compound B has a composition weight ratio of 10: 0 to 5: 5, and The weight ratio with the paracresol mixture is in the range of 1:10 to 1: 1 and the weight average molecular weight of the novolak resin is 3,000 to 15,000.
A novolak resin composition for a positive photoresist, characterized in that:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16575389A JP2948235B2 (en) | 1989-06-28 | 1989-06-28 | Novolak resin composition for positive photoresist |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16575389A JP2948235B2 (en) | 1989-06-28 | 1989-06-28 | Novolak resin composition for positive photoresist |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0329949A JPH0329949A (en) | 1991-02-07 |
| JP2948235B2 true JP2948235B2 (en) | 1999-09-13 |
Family
ID=15818411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16575389A Expired - Lifetime JP2948235B2 (en) | 1989-06-28 | 1989-06-28 | Novolak resin composition for positive photoresist |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2948235B2 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5188921A (en) * | 1989-09-07 | 1993-02-23 | Ocg Microelectronic Materials, Inc. | Selected block copolymer novolak binder resins in radiation-sensitive resist compositions |
| US5235022A (en) * | 1989-09-07 | 1993-08-10 | Ocg Microelectronic Materials, Inc. | Selected block copolymer novolak binder resins |
| US5234795A (en) * | 1989-09-07 | 1993-08-10 | Ocg Microelectronic Materials, Inc. | Process of developing an image-wise exposed resist-coated substrate |
| US5196289A (en) * | 1989-09-07 | 1993-03-23 | Ocg Microelectronic Materials, Inc. | Selected block phenolic oligomers and their use in radiation-sensitive resist compositions |
| US5232819A (en) * | 1989-09-07 | 1993-08-03 | Ocg Microelectronic Materials, Inc. | Selected block phenolic oligomers and their use in phenolic resin compositions and in radiation-sensitive resist compositions |
| US5413894A (en) * | 1993-05-07 | 1995-05-09 | Ocg Microelectronic Materials, Inc. | High ortho-ortho bonded novolak binder resins and their use in radiation-sensitive compositions |
-
1989
- 1989-06-28 JP JP16575389A patent/JP2948235B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0329949A (en) | 1991-02-07 |
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