JP2021113995A - モノマー、ポリマー、及びフォトレジスト組成物 - Google Patents
モノマー、ポリマー、及びフォトレジスト組成物 Download PDFInfo
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- JP2021113995A JP2021113995A JP2021071222A JP2021071222A JP2021113995A JP 2021113995 A JP2021113995 A JP 2021113995A JP 2021071222 A JP2021071222 A JP 2021071222A JP 2021071222 A JP2021071222 A JP 2021071222A JP 2021113995 A JP2021113995 A JP 2021113995A
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- polymer
- photoresist
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- KNCUKAASPPMLPN-UHFFFAOYSA-N CC(CC1)(CCC1OC)OC(C(C)=C)=O Chemical compound CC(CC1)(CCC1OC)OC(C(C)=C)=O KNCUKAASPPMLPN-UHFFFAOYSA-N 0.000 description 1
Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
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- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
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- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
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- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
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Abstract
Description
X及びYが独立して、C、O、またはSであり、かつ炭素脂環式環またはヘテロ脂環式環(XまたはYのうちの1つがヘテロ原子、特にOまたはSである場合、ヘテロ脂環式環)を形成し、
Rが、非水素置換基、そのような任意に置換されたアルキル(例えば、シクロアルキルを含む任意に置換されたC1−20アルキル)、任意に置換されたヘテロアルキル(例えば、任意に置換されたC1−20アルコキシ)、及び任意に置換された炭素環式アリール(任意に置換されたフェニルなど)であり、
R1が、任意に置換されたエーテルまたは任意に置換されたチオエーテルであり、
R2が、アルキルエステル(例えば、C1−20アルキルエステル、例えば、−CH3C(=O)O−、−CH3CH2C(=O)O−)などの非水素置換基であり、
mが、整数、0(この場合、R2基は存在しない)以上の整数であり、
nが、正の整数(例えば、1、2、3、4、5、または6)であり、mとnとの合計が、炭素脂環式環またはヘテロ脂環式環の利用可能な原子価を超えず、
式(I’)において、式中、
X及びYが独立して、C、O、またはSであり、かつ炭素脂環式環またはヘテロ脂環式環(XまたはYのうちの1つがヘテロ原子、特にOまたはSである場合、ヘテロ脂環式環)を形成し、
Rが、非水素置換基、そのような任意に置換されたアルキル(例えば、シクロアルキルを含む任意に置換されたC1−20アルキル)、任意に置換されたヘテロアルキル(例えば、任意に置換されたC1−20アルコキシ)、及び任意に置換された炭素環式アリール(任意に置換されたフェニルなど)であり、
R1が、任意に置換されたエーテルまたは任意に置換されたチオエーテルであり、
R2が、アルキルエステル(例えば、C1−20アルキルエステル、例えば、−CH3C(=O)O−、−CH3CH2C(=O)O−)などの非水素置換基であり、
mが、整数、0(この場合、R2基は存在しない)以上の整数であり、
nが、正の整数(例えば、1、2、3、4、5、または6)であり、mとnとの合計が、炭素脂環式環またはヘテロ脂環式環の利用可能な原子価を超えない。
描写される環式基が、例えば、5〜20個の炭素環原子、好ましくは5または6個の炭素環原子を有する炭素脂環式基であり、
R、R1、R2、m、及びnが、上記の式(I)で定義されるものと同じである。
R、R1、R2、m、及びnが、上記の式(I)で定義されるものと同じである。
式(III′)において、式中、Y’が、水素、または任意に置換されたアルキル、例えば、メチルを含む任意に置換されたC1−6アルキルであり、X、Y、R、R1、R2、m、及びnが、式(I′)で定義されるものと同じであり、
式(IIIA)において、式中、Y’が、水素、または任意に置換されたアルキル、例えば、メチルを含む任意に置換されたC1−6アルキルであり、R、R1、R2、m、及びnが、式(IA)で定義されるものと同じであり、
式(IIIB)において、式中、Y’が、水素、または任意に置換されたアルキル、例
えば、メチルを含む任意に置換されたC1−6アルキルであり、R、R1、R2、m、及びnが、式(II)で定義されるものと同じである。
実施例1:1−エチル−4−メトキシシクロヘキシルメタクリレート(EMCHMA)の合成
4−メトキシシクロヘキサン−1−オン、1−エチル−シクロヘキシルメタクリレート(ECHMA)を実施例1のステップ2と類似の手順で合成した。
4−メトキシシクロヘキサン−1−オン、1−メチルシクロヘキシルメタクリレート(MCHMA)を実施例1のステップ2と類似の手順で合成した。
実施例8〜11に示される一般的な重合手順
異なる量の供給比(表1を参照)で一連のモノマーを、丸底フラスコA中の7:3のエチルラクテート(EL)及びガンマブチロラクトン(GBL)の組成物を含む11.3gの混合溶媒に溶解した。0.51gのジメチル−2,2’−アゾビス−2−メチルプロピオネート(Wako Specialty ChemicalsのV−601アゾ開始剤)を丸底フラスコB中の1.8gの混合EL及びGBL溶液に溶解した。10.8gの混合EL及びBLS溶液を50mlの二口丸底フラスコCに満たした。フラスコC中のこの溶媒をN2ガスでパージし、穏やかに攪拌しながら80℃に加熱した。フラスコB中の溶液をフラスコA中の溶液にゆっくりと添加した。この混合溶液を、シリンジポンプを使用することによって90分の間フラスコCに液滴添加し、次いで、4時間攪拌した。反応混合物を室温に冷却し、重量パーセンテージで9:1のMeOH及びH2Oの337gの溶媒混合物を得た。最終沈殿物をろ過し、16時間乾燥させて標的ポリマーを得た。
3.65gのMCHMA、2.55gのaGBLMA、1.08gのMHLMA、2.72gのHAMAを使用した。(標的ポリマーを一般的な重合手順を使用することによって合成した。標的ポリマーの総収率は、76%(7.61g)であり、8,600のMw、1.57のPDI、及び131.4℃のガラス転移温度を有した。
2.81gのMMCHMA、1.69gのaGBLMA、0.71gのMHLMA、1.80gのHAMAを使用した。標的ポリマーを一般的な重合手順を使用することによって合成した。標的ポリマーの総収率は、51%(3.6g)であり、11,800のMw、1.45のPDI、及び125.4℃のガラス転移温度を有した。
2.91gのEMCHMA、1.64gのaGBLMA、0.69gのMHLMA、1.75gのHAMAを使用した。標的ポリマーを一般的な重合手順を使用することによって合成した。標的ポリマーの総収率は、49%(3.4g)であり、10,000のMw、1.39のPDI、及び135.2℃のガラス転移温度を有した。
2.66gのECHMA、1.74gのaGBLMA、0.74gのMNLMA、1.48gのHAMAを使用した。標的ポリマーを一般的な重合手順を使用することによって合成した。標的ポリマーの総収率は、58%(5.8g)であり、9,900のMw及び1.47のPDIを有した。
PTD(ポジティブトーン現像)用途のためのフォトレジスト調製の一般的な手順
38.85gのポリマー溶液(PGMEA中で15%)、31.04gの1−(4−(tert−ブチル)フェニル)テトラヒドロ−1H−チオフェン−1−イウム2−(2−((1S,2R,4R)−ビシクロ[2.2.1]ヘプタン−2−イル)−1,1,2,2−テトラフルオロエトキシ)−1,1,2,2−テトラフルオロエタン−1−スルホネート溶液(メチル−2−ヒドロキシイソブチレート中で2%)、5.03gのtert−ブチル(1,3−ジヒドロキシ−2−(ヒドロキシメチル)プロパン−2−イル)カルバメート溶液(メチル−2−ヒドロキシイソブチレート中で1%)、0.85gのポリマー(GAM−DFPA/ECPMA(1−エチルシクロペンチルメタクリレート))溶液(PGMEA中で23.6%)、17.64gのPGMEA、及び6.59gのメチル−2−ヒドロキシイソブチレートを混合し、ナイロンフィルターでろ過した。
フォトレジスト1を、フォトレジスト調製の一般的な手順を用いて実施例8で調製したポリマーを使用することによって調製した。
フォトレジスト2を、フォトレジスト調製の一般的な手順を用いて実施例9で調製したポリマーを使用することによって調製した。
フォトレジスト3を、フォトレジスト調製の一般的な手順を用いて実施例10で調製したポリマーを使用することによって調製した。
フォトレジスト4を、フォトレジスト調製の一般的な手順を用いて実施例11で調製したポリマーを使用することによって調製した。
液浸リソグラフィ試験のために、レジスト及び下位の反射防止コーティング(BARC)、ならびにベーキングを、300mmのシリコンウエハを有するLithius Track(TEL,Tokyo Electron Co.)を用いて実施した。露光をNikon S610C液浸193nmスキャナーを用いて行った。露光したウエハを、Lithiusを使用することによって2.38%の水酸化テトラメチルアンモニウム(TMAH)中で現像した。
図5のリソグラフィ能力に関して、MMCHMAをMCHMAと比較し、EMCHMAもECHMAと比較した。より極性の離脱基としてMMCHMAは、密なライン及び単離溝パターンでMCHMAより傾斜なプロファイルを示す。また、EMCHMAは、ECHMAと比較したとき類似の傾向を示す。この傾斜プロファイルがEL及びDoFマージン、ならびにLWRに影響を与えると考えられる。エーテル離脱基(MMCHMA及びEMCHMA)は、対照(MCPMA及びECHMA)より劣るEL及びDoFマージン、ならびにLWRを示す。より親水性の特性及びより低いTgによりエーテル離脱基が対照より速く溶解すると予測されるため、それらの光速度(Eop:最適エネルギー)は、対照より速いスピードを有する。興味深い点は、極性離脱基が単離ラインで対照よりはるかに速いEopを有することである。これは、単離ラインと密なラインとの間のEopバイアスがより小さいことを意味する。極性離脱基を有するポリマーが、TMAH溶液中において、密なライン及び単離溝より、比較的濃い酸濃度を有する単離ラインではるかに簡単に非ブロック化及び現像されると考えられ、より小さな単離ラインCDをもたらす。
17.44gのポリマー(IPAMA(1−イソプロピル−アダマンタニルメタクリレート)/IPCPMA(1−イソプロピル−シクロペンチルメタクリレート)/aGBLMA/X−GM−HL−2)溶液(PGMEA中で15%)、38.75gのトリフェニルスルホニウム4−(((3r,5r,7r)−アダマンタン−1−カルボニル)オキシ)−1,1,2,2−テトラフルオロブタン−1−スルホネート(フルネーム)溶液(メチル−2−ヒドロキシイソブチレート中で1%)、4.58gの(4−(tert−ブチル)フェニル)ジフェニルスルホニウム((3s,5s,7s)−アダマンタン(adamantan)−1−イル)スルファメート(フルネーム)溶液(メチル−2−ヒドロキシイソブチレート中で2%)、1.99gのトリオクチルアミン(フルネーム)溶液(PGMEA中の1%)、1.24gの1−ブチル5−イソブチル2,2,4,4−テトラメチルペンタンジオアートポリマー(PGMEA中の5%)、20.78gのPGMEA、9.69gのガンマ−ブチロラクトン、及び5.52gのメチル−2−ヒドロキシイソブチレートを混合し、ナイロンフィルターでろ過した。
17.44gのポリマー(MMCHMA/IPAMA(1−イソプロピル−アダマンタニルメタクリレート)/IPCPMA(1−イソプロピル−シクロペンチルメタクリレート)/aGBLMA/X−GM−HL−2)溶液(PGMEA中で15%)、38.75gのトリフェニルスルホニウム4−(((3r,5r,7r)−アダマンタン−1−カルボニル)オキシ)−1,1,2,2−テトラフルオロブタン−1−スルホネート溶液(メチル−2−ヒドロキシイソブチレート中で1%)、4.58gの(4−(tert−ブチル)フェニル)ジフェニルスルホニウム((3s,5s,7s)−アダマンタン−1−イル)スルファメート溶液(メチル−2−ヒドロキシイソブチレート中で2%)、1.99gのトリオクチルアミン溶液(PGMEA中の1%)、1.24gの1−ブチル5−イソブチル2,2,4,4−テトラメチルペンタンジオアートポリマー溶液(PGMEA中の5%)、20.78gのPGMEA、9.69gのガンマ−ブチロラクトン、及び5.52gのメチル−2−ヒドロキシイソブチレートを混合し、ナイロンフィルターでろ過した。
300mmのHMDS下塗りシリコンウエハをAR(商標)26N(Rohm and Haas Electronic Materials)でスピンコーティングして、TEL CLEAN TRAC LITHIUS i+上に第1の底部反射防止コーティング(BARC)を形成し、続いて、205℃で60秒間ベーク処理して、900Åの第1のBARC層厚さを提供した。
Claims (5)
- Y’が、水素またはメチル基であり、Rが、メチル基またはエチル基であり、R1が、メトキシ基である、請求項1に記載のフォトレジスト組成物。
- 前記第2のポリマーと前記第1のポリマーの間の表面エネルギーの差が2〜32mN/mである、請求項1または2に記載のフォトレジスト組成物。
- フォトレジスト組成物を処理する方法であって、
基板上に請求項1〜3のいずれか1項に記載のフォトレジスト組成物の層を適用することと、
前記フォトレジスト組成物層を活性化放射に露光することと、
前記露光されたフォトレジスト組成物を現像して、フォトレジストレリーフ画像を提供することと、を含む、方法。 - 前記フォトレジスト組成物層が、液浸露光される、請求項4に記載の方法。
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US11487203B2 (en) | 2022-11-01 |
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CN108264605A (zh) | 2018-07-10 |
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