JP2017110223A - 重合体、有機膜組成物、およびパターン形成方法 - Google Patents
重合体、有機膜組成物、およびパターン形成方法 Download PDFInfo
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- JP2017110223A JP2017110223A JP2016244691A JP2016244691A JP2017110223A JP 2017110223 A JP2017110223 A JP 2017110223A JP 2016244691 A JP2016244691 A JP 2016244691A JP 2016244691 A JP2016244691 A JP 2016244691A JP 2017110223 A JP2017110223 A JP 2017110223A
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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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
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Abstract
【解決手段】本発明の一実施形態に係る重合体は、下記の化学式1で表される構造単位を含む。
(前記化学式1の定義は、明細書中の定義と同様である。)
【選択図】図1
Description
Ar1およびAr2は、それぞれ独立して、置換もしくは非置換のフェニレン基、または置換もしくは非置換のベンゼン環2個〜4個が縮合されている芳香族環基であり、
A1およびA2は、それぞれ独立して、置換もしくは非置換の芳香族環基であって、A1およびA2のうちの少なくとも一つは水素結合可能基により置換されており、A1における水素結合可能基の個数とA2における水素結合可能基の個数との合計は、3個以上であり、
Lは、2価の有機基であり、
*は、連結点である。
aおよびbは、それぞれ独立して、0または1であり、
cは、1〜5である整数であり、
Y1〜Y4は、それぞれ独立して、下記グループ2から選択されたいずれか一つの化合物から誘導された基が置換もしくは非置換されたものであり、
*は、連結点である。
M、M’およびM’’は、それぞれ独立して、置換もしくは非置換のC1〜C10アルキレン基、O、S、SO2、CRaRb、NRc、またはカルボニル基であり、ここでRa、RbおよびRcは、それぞれ独立して、水素原子、置換もしくは非置換のC1〜C10アルキル基、置換もしくは非置換のC6〜C30アリール基、ハロゲン原子またはこれらの組み合わせであり、
rは、0〜10である整数であり、
sは、3〜10である整数である。
R1〜R6は、それぞれ独立して、ヒドロキシ基、アミノ基、またはこれらの組み合わせであり、
n1〜n6は、それぞれ独立して、0〜3である整数であり、ただし、n1およびn2の合計とn3〜n6の合計は、それぞれ独立して、3以上であり、
Z1およびZ2は、それぞれ独立して、ヒドロキシ基、メトキシ基、エトキシ基、ハロゲン基、置換もしくは非置換のC1〜C30アルキル基、置換もしくは非置換のC6〜C30アリール基、置換もしくは非置換のC1〜C30アルコキシ基、またはこれらの組み合わせであり、
k1およびk2は、それぞれ独立して、0〜4である整数であり、
Lは、2価の有機基であり、
*は、連結点である。
Xは、少なくとも一つの水素結合可能基で置換された芳香族環、または少なくとも一つの水素結合可能基で置換されたヘテロ芳香族環基であり、
Lは、2価の有機基であり、
*は、連結点である。
Ar1およびAr2は、それぞれ独立して、置換もしくは非置換のフェニレン基、または置換もしくは非置換のベンゼン環2個〜4個が縮合されている芳香族環基であり、
A1およびA2は、それぞれ独立して、置換もしくは非置換の芳香族環基であって、A1およびA2のうちの少なくとも一つは、水素結合可能基により置換されており、A1における水素結合可能基の個数とA2における水素結合可能基の個数との合計は、3個以上であり、
Lは、2価の有機基であり、
*は、連結点である。
aおよびbは、それぞれ独立して、0または1であり、
cは、1〜5である整数であり、
Y1〜Y4は、それぞれ独立して、下記グループ2から選択されたいずれか一つの化合物から誘導された基が置換もしくは置換されていないものであり、
*は、連結点である。
M、M’およびM’’は、それぞれ独立して、置換もしくは非置換のC1〜C10アルキレン基、O、S、SO2、CRaRb、NRc、またはカルボニル基であり、ここでRa、RbおよびRcは、それぞれ独立して、水素、置換もしくは非置換のC1〜C10アルキル基、置換もしくは非置換のC6〜C30アリール基、ハロゲン原子またはこれらの組み合わせであり、
rは、0〜10である整数であり、
sは、3〜10である整数である。
R1〜R6は、それぞれ独立して、ヒドロキシ基、アミノ基、またはこれらの組み合わせであり、
n1〜n6は、それぞれ独立して、0〜3である整数であるが、ただし、n1およびn2の合計とn3〜n6の合計は、それぞれ独立して、3以上であり、
Z1およびZ2は、それぞれ独立して、ヒドロキシ基、メトキシ基、エトキシ基、ハロゲン基、置換もしくは非置換のC1〜C30アルキル基、置換もしくは非置換のC6〜C30アリール基、置換もしくは非置換のC1〜C30アルコキシ基、またはこれらの組み合わせであり、
k1およびk2は、それぞれ独立して、0〜4である整数であり、
Lは、2価の有機基であり、
*は、連結点である。
Xは、少なくとも一つの水素結合可能基で置換された芳香族環基、または少なくとも一つの水素結合可能基で置換されたヘテロ芳香族環基であり、
Lは、2価の有機基であり、
*は、連結点である。
以下、前述した有機膜組成物を用いてパターンを形成する方法について説明する。
合成例1
フラスコに4,4’−(9H−フルオレン−9,9−ジイル)ジベンゼン−1,2−ジオール(4,4’−(9H−fluorene−9,9−diyl)dibenzene−1,2−diol)(38g)、1,4−ビス(メトキシメチル)ベンゼン(1,4−bis(methoxymethyl)benzene)17g、プロピレングリコールモノメチルエーテルアセテート(PGMEA)82gおよびジエチルスルフェート(diethylsulfate)0.5gを投入し、100℃で攪拌して重合反応を行った。重量平均分子量が2,000〜3,500である時に反応を完了した。重合反応が完了した後、反応物を常温で徐々に冷却させた後、前記反応物を蒸留水40gおよびメタノール400gに投入して強く攪拌して、放置させた。上澄液を除去し、沈殿物をプロピレングリコールモノメチルエーテルアセテート(PGMEA)80gに溶かした後、メタノール320g、蒸留水320gを用いて強く攪拌した後、放置させた(1次工程)。この時に得られる上澄液を再び除去し、沈殿物をプロピレングリコールモノメチルエーテルアセテート(PGMEA)80gに溶解させた(2次工程)。前記1次および2次工程を1回の精製工程とし、この精製工程を合計3回実施した。精製が終わった重合体をプロピレングリコールモノメチルエーテルアセテート(PGMEA)80gに溶かした後、減圧下で溶液に残っているメタノールおよび蒸溜水を除去して下記の化学式1aで表される構造単位を含む重合体を得た(Mw:3,500)。
6,6’−(9H−フルオレン−9,9−ジイル)ジナフタレン−1,2−ジオール(6,6’−(9H−fluorene−9,9−diyl)dinaphthalene−1,2−diol)(48g)、1,3−bis(メトキシメチル)ベンゼン(1,3−bis(methoxymethyl)benzene)17g、プロピレングリコールモノメチルエーテルアセテート(PGMEA)98gおよびジエチルスルフェート(diethylsulfate)0.5gを用いて合成例1と同様な合成過程を経て化学式1bで表される構造単位を含む重合体を得た(Mw:3,500)。
ピレン−1,6−ジオール(pyrene−1,6−diol)(23g)、1,4−ビス(メトキシメチル)ベンゼン(1,4−bis(methoxymethyl)benzene)(34g)、4,4’−(9H−フルオレン−9,9−ジイル)ジベンゼン−1,2−ジオール(4,4’−(9H−fluorene−9,9−diyl)dibenzene−1,2−diol)38g、プロピレングリコールモノメチルエーテルアセテート(PGMEA)143gおよびジエチルスルフェート(diethylsulfate)0.7gを用いて合成例1と同様な合成過程を経て化学式1cで表される構造単位を含む重合体を得た(Mw:3,200)。
4,4’−(9H−フルオレン−9,9−ジイル)ジベンゼン−1,2−ジオール(4,4’−(9H−fluorene−9,9−diyl)dibenzene−1,2−diol)(38g)、4,4’−(プロパン−2,2−ジイル)ビス((4−(メトキシメチル)フェノキシ)ベンゼン)(4,4’−(propane−2,2−diyl)bis((4−(methoxymethyl)phenoxy)benzene))(47g)、プロピレングリコールモノメチルエーテルアセテート(PGMEA)128gおよびジエチルスルフェート(diethylsulfate)0.5gを用いて合成例1と同様な合成過程を経て化学式1dで表される構造単位を含む重合体を得た(Mw:3,500)。
5,5’−(9H−フルオレン−9,9−ジイル)ジベンゼン−1,2,3−トリオール(5,5’−(9H−fluorene−9,9−diyl)dibenzene−1,2,3−triol)(41g)、4,4’−オキシビス((メトキシメチル)ベンゼン)(4,4’−oxybis((methoxymethyl)benzene))(47g)、プロピレングリコールモノメチルエーテルアセテート(PGMEA)133gおよびジエチルスルフェート(diethylsulfate)0.5gを用いて合成例1と同様な合成過程を経て化学式1eで表される構造単位を含む重合体を得た(Mw:3,100)。
5,5’−(9H−フルオレン−9,9−ジイル)ジベンゼン−1,2,3−トリオール(5,5’−(9H−fluorene−9,9−diyl)dibenzene−1,2,3−triol)(41g)、1,6−ビス(4−(メトキシメチル)フェノキシ)ヘキサン(1,6−bis(4−(methoxymethyl)phenoxy)hexane)(36g)、プロピレングリコールモノメチルエーテルアセテート(PGMEA)116gおよびジエチルスルフェート(diethylsulfate)0.5gを用いて合成例1と同様な合成過程を経て化学式1fで表される構造単位を含む重合体を得た(Mw:3,200)。
5,5’−(9H−フルオレン−9,9−ジイル)ジベンゼン−1,2,3−トリオール(5,5’−(9H−fluorene−9,9−diyl)dibenzene−1,2,3−triol)(20g)、1,3−bis(メトキシメチル)ベンゼン(1,3−bis(methoxymethyl)benzene)(17g)、1H−インドール−5−オール(1H−indol−5−ol)(7g)、プロピレングリコールモノメチルエーテルアセテート(PGMEA)103gおよびジエチルスルフェート(diethylsulfate)0.5gを用いて合成例1と同様な合成過程を経て化学式1gで表される構造単位を含む重合体を得た(Mw:3,000)。
5,5’−(9H−フルオレン−9,9−ジイル)ジベンゼン−1,2,3−トリオール(5,5’−(9H−fluorene−9,9−diyl)dibenzene−1,2,3−triol)(20g)、4,4’−オキシビス((メトキシメチル)ベンゼン)(4,4’−oxybis((methoxymethyl)benzene))(26g)、1H−インドール(1H−indol)(6g)、プロピレングリコールモノメチルエーテルアセテート(PGMEA)123gおよびジエチルスルフェート(diethylsulfate)0.5gを用いて合成例1と同様な合成過程を経て化学式1hで表される構造単位を含む重合体を得た(Mw:3,500)。
6,6’−(9H−フルオレン−9,9−ジイル)ジナフタレン−1,2−ジオール(6,6’−(9H−fluorene−9,9−diyl)dinaphthalene−1,2−diol)(48g)、4−ヒドロキシベンズアルデヒド(4−hydroxybenzaldehyde)(12g)、プロピレングリコールモノメチルエーテルアセテート(PGMEA)141gおよびジエチルスルフェート(diethylsulfate)0.3gを用いて合成例1と同様な合成過程を経て化学式1iで表される構造単位を含む重合体を得た(Mw:3,500)。
4,4’−(9H−フルオレン−9,9−ジイル)ジベンゼン−1,2−ジオール(4,4’−(9H−fluorene−9,9−diyl)dibenzene−1,2−diol)(38g)、4−ヒドロキシ−1−ナフトアルデヒド(4−hydroxy−1−naphthaldehyde)(17g)、プロピレングリコールモノメチルエーテルアセテート(PGMEA)129gおよびジエチルスルフェート(diethylsulfate)0.3gを用いて合成例1と同様な合成過程を経て化学式1jで表される構造単位を含む重合体を得た(Mw:3,200)。
4,4’−(9H−フルオレン−9,9−ジイル)ジベンゼン−1,2−ジオール(4,4’−(9H−fluorene−9,9−diyl)dibenzene−1,2−diol)(19g)、2−ヒドロキシ−1−ナフトアルデヒド(2−hydroxy−1−naphthaldehyde)(17g)、ナフタレン−1−オール(naphthalen−1−ol)(7g)、プロピレングリコールモノメチルエーテルアセテート(PGMEA)91gおよびp−トルエンスルホン酸−水和物(0.3g)を用いて合成例1と同様な合成過程を経て化学式1kで表される構造単位を含む重合体を得た(Mw:3,000)。
4,4’−(9H−フルオレン−9,9−ジイル)ジベンゼン−1,2−ジオール(4,4’−(9H−fluorene−9,9−diyl)dibenzene−1,2−diol)(19g)、4,4’−オキシビス((メトキシメチル)ベンゼン)(4,4’−oxybis((methoxymethyl)benzene))(26g)、ナフタレン−2−オール(naphthalen−2−ol)(7g)、プロピレングリコールモノメチルエーテルアセテート(PGMEA)122gおよびジエチルスルフェート(diethylsulfate)0.5gを用いて合成例1と同様な合成過程を経て化学式1lで表される構造単位を含む重合体を得た(Mw:3,100)。
ベンゾペリレン(23g)、1,4−ビス(メトキシメチル)ベンゼン(1,4−bis(methoxymethyl)benzene)17g、プロピレングリコールモノメチルエーテルアセテート(PGMEA)60g、およびジエチルスルフェート(diethylsulfate)(1.23g)を投入した後、100℃で2〜24時間攪拌して重合反応を行った。重量平均分子量が2,000〜3,500である時に反応を完了した。重合反応が完了した後、反応物を常温で徐々に冷却させた後、前記反応物を蒸溜水40gおよびメタノール400gに投入して強く攪拌して、定置させた。上澄液を除去し、沈殿物をシクロヘキサノン(cyclohexanone)80gに溶かした後、メタノール320gを用いて強く攪拌した後、定置させた(1次)。この時に得られる上澄液を再び除去し、沈殿物をシクロヘキサノン80gに溶かした(2次)。合成例1と同様に精製過程を経て化学式Xで表される構造単位を含む重合体を得た(Mw:2,700)。
6,6’−(9H−フルオレン−9,9−ジイル)ジナフタレン−2−オール(6,6’−(9H−fluorene−9,9−diyl)dinaphthalen−2−ol)(45g)、1,4−ビス(メトキシメチル)ベンゼン(1,4−bis(methoxymethyl)benzene)17g、プロピレングリコールモノメチルエーテルアセテート(PGMEA)62g、およびジエチルスルフェート(diethylsulfate)(0.6g)を用いて合成例1と同様な合成過程を経て化学式Yで表される構造単位を含む重合体を得た(Mw:3,500)。
実施例1
合成例1で得られた重合体をプロピレングリコールモノメチルエーテルアセテート(propylene glycol monomethyl ether acetate、PGMEA)とシクロヘキサノン(cyclohexanone)(7:3(v/v))の混合溶媒に溶かした後、濾過してハードマスク組成物を製造した。目的とする厚さにより前記化合物の含有量は前記ハードマスク組成物の総重量に対して1〜20重量%の含有量の範囲で調節した。
合成例1で得られた重合体の代わりに、合成例2〜12から得られた重合体をそれぞれ用いたことを除いては、実施例1と同様な方法でハードマスク組成物を製造した。
合成例1で得られた重合体の代わりに、比較合成例1および2で得られた重合体をそれぞれ用いたことを除いては、実施例1と同様な方法でハードマスク組成物を製造した。
ホールパターンが形成されたシリコンウエハーの上に実施例1〜12と、比較例1および2によるハードマスク組成物をスピンオンコーティングして薄膜を形成した後、断面をV−SEM装置を用いて観察した。前記ハードマスク組成物内の重合体の含有量はベアウエハー上での薄膜の厚さが2,000Åになるように調節した。
ホールパターンが形成されたシリコンウエハーの上に実施例1〜5、7、8、11、および12、そして比較例1および2によるハードマスク組成物をスピンオンコーティングして400℃、2分間でベーク工程を経て薄膜を形成した後、断面をV−SEM装備を用いて観察した。前記ハードマスク組成物内の化合物の含有量はベアウエハー上での薄膜の厚さが1,400Åになるように調節した。
Claims (12)
- 下記の化学式1で表される構造単位を含む重合体:
Ar1およびAr2は、それぞれ独立して、置換もしくは非置換のフェニレン基、または置換もしくは非置換のベンゼン環2個〜4個が縮合されている芳香族環基であり、
A1およびA2は、それぞれ独立して、置換もしくは非置換の芳香族環基であって、A1およびA2のうちの少なくとも一つは、水素結合可能基により置換されており、A1における水素結合可能基の個数とA2における水素結合可能基の個数との合計は、3個以上であり、
Lは、2価の有機基であり、
*は、連結点である。 - 前記水素結合可能基は、ヒドロキシ基、アミノ基、またはこれらの組み合わせである、請求項1に記載の重合体。
- 前記A1およびA2は、それぞれ独立して、下記グループ1から選択されるいずれか一つの化合物から誘導された芳香族環基が置換もしくは置換されていないものである、請求項1または2に記載の重合体:
- 前記Lは、下記の化学式Z1〜化学式Z4のうちのいずれか一つで表される、請求項1〜3のいずれか1項に記載の重合体:
aおよびbは、それぞれ独立して、0または1であり、
cは、1〜5である整数であり、
Y1〜Y4は、それぞれ独立して、下記グループ2から選択されるいずれか一つの化合物から誘導された基が置換もしくは置換されていないものであり、
*は、連結点である。
M、M’およびM’’は、それぞれ独立して、置換もしくは非置換のC1〜C10アルキレン基、O、S、SO2、CRaRb、NRc、またはカルボニル基であり、ここでRa、RbおよびRcは、それぞれ独立して、水素原子、置換もしくは非置換のC1〜C10アルキル基、置換もしくは非置換のC6〜C30アリール基、ハロゲン原子またはこれらの組み合わせであり、
rは、0〜10である整数であり、
sは、3〜10である整数である。 - 前記A1における水素結合可能基の個数とA2における水素結合可能基の個数との合計は、3個以上6個以下である、請求項1〜4のいずれか1項に記載の重合体。
- 前記化学式1で表される構造単位は、下記の化学式1−1〜1−2のうちのいずれか一つで表される、請求項1〜5のいずれか1項に記載の重合体:
R1〜R6は、それぞれ独立して、ヒドロキシ基、アミノ基、またはこれらの組み合わせであり、
n1〜n6は、それぞれ独立して、0〜3である整数であり、ただし、n1およびn2の合計とn3〜n6の合計は、それぞれ独立して、3以上であり、
Z1およびZ2は、それぞれ独立して、ヒドロキシ基、メトキシ基、エトキシ基、ハロゲン基、置換もしくは非置換のC1〜C30アルキル基、置換もしくは非置換のC6〜C30アリール基、置換もしくは非置換のC1〜C30アルコキシ基、またはこれらの組み合わせであり、
k1およびk2は、それぞれ独立して、0〜4である整数であり、
Lは、2価の有機基であり、
*は、連結点である。 - 下記の化学式2で表される構造単位をさらに含む、請求項1〜6のいずれか1項に記載の重合体:
Xは、少なくとも一つの水素結合可能基で置換された芳香族環基、または少なくとも一つの水素結合可能基で置換されたヘテロ芳香族環基であり、
Lは、2価の有機基であり、
*は、連結点である。 - 前記化学式2における水素結合可能基は、ヒドロキシ基、アミノ基、またはこれらの組み合わせである、請求項7に記載の重合体。
- 重量平均分子量は、500〜200,000である、請求項1〜8のいずれか1項に記載の重合体。
- 請求項1〜9のいずれか1項に記載の重合体と、
溶媒と、
を含む有機膜組成物。 - 基板上に材料層を形成する段階と、
前記材料層上に請求項10に記載の有機膜組成物を塗布する段階と、
前記有機膜組成物を熱処理してハードマスク層を形成する段階と、
前記ハードマスク層上にシリコン含有薄膜層を形成する段階と、
前記シリコン含有薄膜層上にフォトレジスト層を形成する段階と、
前記フォトレジスト層を露光および現像してフォトレジストパターンを形成する段階と、
前記フォトレジストパターンを用いて前記シリコン含有薄膜層および前記ハードマスク層を選択的に除去し、前記材料層の一部を露出する段階と、
前記材料層の露出した部分をエッチングする段階と、
を含むパターン形成方法。 - 前記有機膜組成物を塗布する段階を、スピンオンコーティング法により行う、請求項11に記載のパターン形成方法。
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