JP4355939B2 - 半導体装置の絶縁膜形成用組成物およびシリカ系膜の形成方法 - Google Patents
半導体装置の絶縁膜形成用組成物およびシリカ系膜の形成方法 Download PDFInfo
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- JP4355939B2 JP4355939B2 JP2004216346A JP2004216346A JP4355939B2 JP 4355939 B2 JP4355939 B2 JP 4355939B2 JP 2004216346 A JP2004216346 A JP 2004216346A JP 2004216346 A JP2004216346 A JP 2004216346A JP 4355939 B2 JP4355939 B2 JP 4355939B2
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- OJAJJFGMKAZGRZ-UHFFFAOYSA-N trimethyl(phenoxy)silane Chemical compound C[Si](C)(C)OC1=CC=CC=C1 OJAJJFGMKAZGRZ-UHFFFAOYSA-N 0.000 description 1
- PHPGKIATZDCVHL-UHFFFAOYSA-N trimethyl(propoxy)silane Chemical compound CCCO[Si](C)(C)C PHPGKIATZDCVHL-UHFFFAOYSA-N 0.000 description 1
- PGZGBYCKAOEPQZ-UHFFFAOYSA-N trimethyl-[(2-methylpropan-2-yl)oxy]silane Chemical compound CC(C)(C)O[Si](C)(C)C PGZGBYCKAOEPQZ-UHFFFAOYSA-N 0.000 description 1
- FNNJGIKXHZZGCV-UHFFFAOYSA-N triphenoxy(propan-2-yl)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(C(C)C)OC1=CC=CC=C1 FNNJGIKXHZZGCV-UHFFFAOYSA-N 0.000 description 1
- AMUIJRKZTXWCEA-UHFFFAOYSA-N triphenoxy(propyl)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(CCC)OC1=CC=CC=C1 AMUIJRKZTXWCEA-UHFFFAOYSA-N 0.000 description 1
- MUCRQDBOUNQJFE-UHFFFAOYSA-N triphenoxy(triphenoxysilyl)silane Chemical compound C=1C=CC=CC=1O[Si]([Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 MUCRQDBOUNQJFE-UHFFFAOYSA-N 0.000 description 1
- QDOHRQCMIFOPEY-UHFFFAOYSA-N tripropoxy(2-tripropoxysilylethyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)CC[Si](OCCC)(OCCC)OCCC QDOHRQCMIFOPEY-UHFFFAOYSA-N 0.000 description 1
- VUWVDNLZJXLQPT-UHFFFAOYSA-N tripropoxy(propyl)silane Chemical compound CCCO[Si](CCC)(OCCC)OCCC VUWVDNLZJXLQPT-UHFFFAOYSA-N 0.000 description 1
- BZIXIRYKSIMLOB-UHFFFAOYSA-N tripropoxy(tripropoxysilylmethyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)C[Si](OCCC)(OCCC)OCCC BZIXIRYKSIMLOB-UHFFFAOYSA-N 0.000 description 1
- NBAPKCYEEBMZDW-UHFFFAOYSA-N tripropoxy-(2-tripropoxysilylphenyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)C1=CC=CC=C1[Si](OCCC)(OCCC)OCCC NBAPKCYEEBMZDW-UHFFFAOYSA-N 0.000 description 1
- YMAKWPVRMIUZBP-UHFFFAOYSA-N tripropoxy-(3-tripropoxysilylphenyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)C1=CC=CC([Si](OCCC)(OCCC)OCCC)=C1 YMAKWPVRMIUZBP-UHFFFAOYSA-N 0.000 description 1
- OZWKZRFXJPGDFM-UHFFFAOYSA-N tripropoxysilane Chemical compound CCCO[SiH](OCCC)OCCC OZWKZRFXJPGDFM-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- ZZEMYLNHCSTIPH-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[2-[tris[(2-methylpropan-2-yl)oxy]silyl]phenyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C1=CC=CC=C1[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C ZZEMYLNHCSTIPH-UHFFFAOYSA-N 0.000 description 1
- PITXUFPLSLHXRV-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[4-[tris[(2-methylpropan-2-yl)oxy]silyl]phenyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C1=CC=C([Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C)C=C1 PITXUFPLSLHXRV-UHFFFAOYSA-N 0.000 description 1
- QJJZQRNPNLTSNS-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[tris[(2-methylpropan-2-yl)oxy]silylmethyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C QJJZQRNPNLTSNS-UHFFFAOYSA-N 0.000 description 1
- MBTOFLNIAAISNI-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-prop-2-enylsilane Chemical compound CC(C)(C)O[Si](CC=C)(OC(C)(C)C)OC(C)(C)C MBTOFLNIAAISNI-UHFFFAOYSA-N 0.000 description 1
- MJIHPVLPZKWFBL-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-propan-2-ylsilane Chemical compound CC(C)(C)O[Si](C(C)C)(OC(C)(C)C)OC(C)(C)C MJIHPVLPZKWFBL-UHFFFAOYSA-N 0.000 description 1
- DIZPPYBTFPZSGK-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-propylsilane Chemical compound CCC[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C DIZPPYBTFPZSGK-UHFFFAOYSA-N 0.000 description 1
- QCKKBOHAYRLMQP-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]silane Chemical compound CC(C)(C)O[SiH](OC(C)(C)C)OC(C)(C)C QCKKBOHAYRLMQP-UHFFFAOYSA-N 0.000 description 1
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- 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
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Description
(a)光酸発生剤、光塩基発生剤、増感剤などのイオン性物質、電荷キャリアもしくは腐食性化合物の発生源を含まず、短時間で硬化可能な有機シリカゾル組成物、
(b)トランジスタ構造へのダメージが無く、枚葉プロセスで処理可能な有機シリカ系膜のキュア方法、
(c)吸湿性がなく疎水性に富んだ有機シリカ系膜、
(d)銅ダマシン構造の形成に耐えうる機械的強度を有する有機シリカ系膜、
がLSI用半導体装置の低誘電率層間絶縁膜およびその形成方法として望まれている。
(R9)a−Si−(OR10)4−a・・・(B)
(式中、R9、R10はアルキル基、アリール基、aは0〜3の整数を表す)
R11 b(R12O)3−bSi−(R15)d−Si(OR13)3−cR14 c・・・(C)
[式中、R11〜R14は同一または異なり、それぞれアルキル基、アリール基を示し、bおよびcは同一または異なり、0〜2の数を示し、R15は酸素原子、フェニレン基または−(CH2)m−で表される基(ここで、mは1〜6の整数である)、dは0または1を示す。]
前記塗膜を加熱する工程と、
前記塗膜に紫外線を照射して硬化処理を行う工程と、を含む。
本発明に係る膜形成用組成物は、下記一般式(A)で表される化合物の群から選ばれた少なくとも1種のシラン化合物と、下記一般式(B)、(C)で表される化合物の群から選ばれた少なくとも2種以上のシラン化合物とを加水分解、縮合した加水分解縮合物であって、下記一般式(A1)または(A2)で表される炭素−炭素二重結合を含む有機基を含有する加水分解縮合物(有機シリカゾル)と、有機溶媒と、を含み、熱および紫外線を用いて硬化される。
(R9)a−Si−(OR10)4−a・・・(B)
(式中、R9はアルキル基、アリール基、R10はアルキル基、アリール基、aは0〜3の整数を表す)
R11 b(R12O)3−bSi−(R15)d−Si(OR13)3−cR14 c・・・(C)
[式中、R11〜R14は同一または異なり、それぞれアルキル基、アリール基を示し、bおよびcは同一または異なり、0〜2の数を示し、R15は酸素原子、フェニレン基または−(CH2)m−で表される基(ここで、mは1〜6の整数である)、dは0または1を示す。]
前記一般式(A)で表される化合物(以下、「化合物1」ともいう)、前記一般式(B)で表される化合物(以下、「化合物2」ともいう)、前記一般式(C)で表される化合物(以下、「化合物3」ともいう)としては、以下のものを用いることができる。
化合物1は、一般式(A)で表されるように、一般式(A1)または(A2)で示される炭素−炭素二重結合を有する有機基を含むシラン化合物である。
前記一般式(B)において、R9、R10としては、前記一般式(A)のR1〜R8として例示したものと同様の基を挙げることができる。
前記一般式(C)において、R11〜R14としては、前記一般式(A)のR1〜R8として例示したものと同様の基を挙げることができる。
本発明の膜形成用組成物において、前記化合物1で表される化合物の合計の使用量は、60モル%以下、より好ましくは5モル%以上50モル%以下である。化合物1の使用量が60モル%を超えると、一般式(A1)または(A2)で表される置換基同士での重合等の、脱離以外の副反応が起きて好ましくないことがある。
本発明の膜形成用組成物は、上述した化合物1〜3と水を含む有機溶媒を混合し、必要に応じて加熱することにより得ることができる。有機溶媒としては、1.2.で述べるものを用いることができる。
化合物1〜3の加水分解縮合時に使用可能な金属キレート化合物は、下記一般式(1)で表される。
〔式中、R16はキレート剤、Mは金属原子、R17は炭素数2〜5のアルキル基または炭素数6〜20のアリール基を示し、αは金属Mの原子価、βは1〜αの整数を表す。〕
化合物1〜3成分との加水分解縮合時に使用可能な酸性化合物としては、有機酸または無機酸が例示できる。有機酸としては、例えば、酢酸、プロピオン酸、ブタン酸、ペンタン酸、ヘキサン酸、ヘプタン酸、オクタン酸、ノナン酸、デカン酸、シュウ酸、マレイン酸、メチルマロン酸、アジピン酸、セバシン酸、没食子酸、酪酸、メリット酸、アラキドン酸、シキミ酸、2−エチルヘキサン酸、オレイン酸、ステアリン酸、リノール酸、リノレイン酸、サリチル酸、安息香酸、p−アミノ安息香酸、p−トルエンスルホン酸、ベンゼンスルホン酸、モノクロロ酢酸、ジクロロ酢酸、トリクロロ酢酸、トリフルオロ酢酸、ギ酸、マロン酸、スルホン酸、フタル酸、フマル酸、クエン酸、酒石酸、無水マレイン酸、フマル酸、イタコン酸、コハク酸、メサコン酸、シトラコン酸、リンゴ酸、マロン酸、グルタル酸の加水分解物、無水マレイン酸の加水分解物、無水フタル酸の加水分解物などを挙げることができる。無機酸としては、例えば、塩酸、硝酸、硫酸、フッ酸、リン酸などを挙げることができる。なかでも、加水分解および縮合反応中のポリマーの析出やゲル化のおそれが少ない点で有機酸が好ましく、このうち、カルボキシル基を有する化合物がより好ましく、なかでも、酢酸、シュウ酸、マレイン酸、ギ酸、マロン酸、フタル酸、フマル酸、イタコン酸、コハク酸、メサコン酸、シトラコン酸、リンゴ酸、マロン酸、グルタル酸、無水マレイン酸の加水分解物が特に好ましい。これらは1種あるいは2種以上を同時に使用してもよい。
化合物1〜3成分との加水分解縮合時に使用可能な塩基性化合物としては、例えば、水酸化ナトリウム、水酸化カリウム、水酸化リチウム、水酸化セリウム、水酸化バリウム、水酸化カルシウム、ピリジン、ピロール、ピペラジン、ピロリジン、ピペリジン、ピコリン、アンモニア、メチルアミン、エチルアミン、プロピルアミン、ブチルアミン、ジメチルアミン、ジエチルアミン、ジプロピルアミン、ジブチルアミン、トリメチルアミン、トリエチルアミン、トリプロピルアミン、トリブチルアミン、モノエタノールアミン、ジエタノールアミン、ジメチルモノエタノールアミン、モノメチルジエタノールアミン、トリエタノールアミン、ジアザビシクロオクラン、ジアザビシクロノナン、ジアザビシクロウンデセン、尿素、テトラメチルアンモニウムハイドロオキサイド、テトラエチルアンモニウムハイドロオキサイド、テトラプロピルアンモニウムハイドロオキサイド、テトラブチルアンモニウムハイドロオキサイド、ベンジルトリメチルアンモニウムハイドロオキサイド、コリン、などを挙げることができる。これらの中で、アンモニア、有機アミン類、アンモニウムハイドロオキサイド類を好ましい例として挙げることができ、テトラメチルアンモニウムハイドロオキサイド、テトラエチルアンモニウムハイドロオキサイド、テトラプロピルアンモニウムハイドロオキサイドが特に好ましい。これらの塩基性化合物は、1種あるいは2種以上を同時に使用してもよい。
本発明においては、シラン化合物1〜3を有機溶媒中で加水分解縮合を行なうことができる。ここで、有機溶媒としては、下記一般式(2)で表される溶剤であることが好ましい。
〔R18およびR19は、それぞれ独立して水素原子、炭素数1〜4のアルキル基またはCH3CO−から選ばれる1価の有機基を示し、γは1〜2の整数を表す。〕
本発明で用いることができる有機溶媒としては、アルコール系溶媒、ケトン系溶媒、アミド系溶媒、エーテル系溶媒、エステル系溶媒、脂肪族炭化水素系溶媒、芳香族系溶媒および含ハロゲン溶媒の群から選ばれた少なくとも1種が挙げられる。
エチレングリコール、1,2−プロピレングリコール、1,3−ブチレングリコール、ペンタンジオール−2,4、2−メチルペンタンジオール−2,4、ヘキサンジオール−2,5、ヘプタンジオール−2,4、2−エチルヘキサンジオール−1,3、ジエチレングリコール、ジプロピレングリコール、トリエチレングリコール、トリプロピレングリコールなどの多価アルコール系溶媒;
エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノプロピルエーテル、エチレングリコールモノブチルエーテル、エチレングリコールモノヘキシルエーテル、エチレングリコールモノフェニルエーテル、エチレングリコールモノ−2−エチルブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノプロピルエーテル、ジエチレングリコールモノブチルエーテル、ジエチレングリコールモノヘキシルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノブチルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノプロピルエーテルなどの多価アルコール部分エーテル系溶媒;などを挙げることができる。これらのアルコール系溶媒は、1種あるいは2種以上を同時に使用してもよい。
本発明の絶縁膜形成用組成物には、有機ポリマー、界面活性剤、シランカップリング剤、などの成分を添加してもよい。また、これらの添加物は、膜形成用組成物を製造する前の、各成分が溶解もしくは分散された溶剤中に添加されていてもよい。
本発明で用いられる有機ポリマーは、シリカ系膜中に空孔を形成するための易分解成分として添加することができる。このような有機ポリマーを添加することは、特開2000−290590号公報、特開2000−313612号公報、Hedrick, J.L.,et al. "Templating Nanoporosity in Thin Film Die lectric Insulators". Adv. Mater., 10 (13), 1049, 1998.等の参考文献で記述されており、同様な有機ポリマーを添加してもよい。
界面活性剤としては、たとえば、ノニオン系界面活性剤、アニオン系界面活性剤、カチオン系界面活性剤、両性界面活性剤などが挙げられ、さらには、フッ素系界面活性剤、シリコーン系界面活性剤、ポリアルキレンオキシド系界面活性剤、ポリ(メタ)アクリレート系界面活性剤などを挙げることができ、好ましくはフッ素系界面活性剤、シリコーン系界面活性剤を挙げることができる。
シランカップリング剤としては、例えば、3−グリシジロキシプロピルトリメトキシシラン、3−アミノグリシジロキシプロピルトリエトキシシラン、3−メタクリロキシプロピルトリメトキシシラン、3−グリシジロキシプロピルメチルジメトキシシラン、1−メタクリロキシプロピルメチルジメトキシシラン、3−アミノプロピルトリメトキシシラン、3−アミノプロピルトリエトキシシラン、2−アミノプロピルトリメトキシシラン、2−アミノプロピルトリエトキシシラン、N−(2−アミノエチル)−3−アミノプロピルトリメトキシシラン、N−(2−アミノエチル)−3−アミノプロピルメチルジメトキシシラン、3−ウレイドプロピルトリメトキシシラン、3−ウレイドプロピルトリエトキシシラン、N−エトキシカルボニル−3−アミノプロピルトリメトキシシラン、N−エトキシカルボニル−3−アミノプロピルトリエトキシシラン、N−トリエトキシシリルプロピルトリエチレントリアミン、N−トリエトキシシリルプロピルトリエチレントリアミン、10−トリメトキシシリル−1,4,7−トリアザデカン、10−トリエトキシシリル−1,4,7−トリアザデカン、9−トリメトキシシリル−3,6−ジアザノニルアセテート、9−トリエトキシシリル−3,6−ジアザノニルアセテート、N−ベンジル−3−アミノプロピルトリメトキシシラン、N−ベンジル−3−アミノプロピルトリエトキシシラン、N−フェニル−3−アミノプロピルトリメトキシシラン、N−フェニル−3−アミノプロピルトリエトキシシラン、N−ビス(オキシエチレン)−3−アミノプロピルトリメトキシシラン、N−ビス(オキシエチレン)−3−アミノプロピルトリエトキシシランなどが挙げられる。これらは、1種あるいは2種以上を同時に使用しても良い。
本発明のシリカ系膜の形成方法は、膜形成用組成物を基板に塗布し、塗膜を形成する工程と、前記塗膜を加熱する工程と、前記塗膜に紫外線を照射して硬化処理を行う工程と、
を含む。
本発明のシリカ系膜は、後述する実施例からも明らかなように、Δkおよび弾性率が極めて高く、低誘電率である。
(a)膜形成用組成物が特定の置換基を有する有機シリカゾルを含むので、比誘電率、弾性率などの絶縁膜特性に優れ、かつ低温かつ短時間で形成できること、
(b)膜形成用組成物が、紫外線活性な酸発生剤、塩基発生剤、増感剤などのイオン性物質、電荷キャリアもしくは腐食性化合物の発生源を含まなくともよいため、半導体装置への汚染物質を含まないこと、
(c)RIEなどの半導体プロセスによるトランジスタ構造へのダメージが極めて少なく、かつ枚葉プロセスで処理可能な硬化方法を採用できること、
(d)疎水性が高く、吸湿性が低いので、低い比誘電率を維持できること、
(e)弾性率などの機械的強度が優れており、例えば銅ダマシン構造の形成に耐えうること、
などの特徴を有する。
以下、本発明を実施例を挙げてさらに具体的に説明する。本発明は以下の実施例に限定されるものではない。なお、実施例および比較例中の「部」および「%」は、特記しない限り、それぞれ重量部および重量%であることを示している。
以下のようにして、膜形成用組成物の製造およびシリカ系膜の形成を行った。
(実施例1)
コンデンサーを備えた石英製フラスコ中に、20%水酸化テトラプロピルアンモニウム水溶液31.8g、超純水143.4g、エタノール448.4gを秤取り、25℃で攪拌した。次いで、化合物1としてビニルトリメトキシシラン36.2g、化合物1以外のシラン化合物としてメチルトリメトキシシラン19.9g、テトラエトキシシラン20.3gを連続的に1時間かけて加えた後、さらに60℃で1時間攪拌した。反応液を室温に冷却後、プロピレングリコールモノプロピルエーテル1183.6gと20%マレイン酸水溶液30.6gを加えた。この反応液を固形分濃度が10%となるまで減圧下で濃縮し、ナトリウム含量0.7ppb、カリウム含量0.4ppbおよび鉄含量1.7ppbである膜形成用組成物1を得た。
コンデンサーを備えた石英製フラスコ中に、25%水酸化テトラメチルアンモニウム水溶液5.6g、超純水181.0g、イソプロパノール460.9gを秤取り、25℃で攪拌した。次いで、化合物1としてビニルトリエトキシシラン11.9g、化合物1以外のシラン化合物としてメチルトリメトキシシラン21.2g、テトラエトキシシラン19.5gを連続的に1時間かけて加えた後、さらに60℃で1時間攪拌した。反応液を室温に冷却後、プロピレングリコールモノプロピルエーテル1283.8gと20%マレイン酸水溶液15.12gを加えた。この反応液を固形分濃度が10%となるまで減圧下で濃縮し、ナトリウム含量0.9ppb、カリウム含量0.6ppbおよび鉄含量1.5ppbである膜形成用組成物2を得た。
コンデンサーを備えた石英製フラスコ中に、25%水酸化テトラメチルアンモニウム水溶液18.0g、超純水283.6g、エタノール306.3gを秤取り、25℃で攪拌した。次いで、化合物1としてアリルトリメトキシシラン16.2g、化合物1以外のシラン化合物としてメチルトリエトキシシラン44.6g、テトラエトキシシラン31.2gを連続的に1時間かけて加えた後、さらに60℃で1時間攪拌した。反応液を室温に冷却後、プロピレングリコールモノプロピルエーテル1179.8gと20%マレイン酸水溶液48.5gを加えた。この反応液を固形分濃度が10%となるまで減圧下で濃縮し、ナトリウム含量1.9ppb、カリウム含量1.6ppbおよび鉄含量1.0ppbである膜形成用組成物3を得た。
コンデンサーを備えた石英製フラスコ中で、化合物1としてメチルビニルジメトキシシラン40.4g、化合物1以外のシラン化合物としてメチルトリメトキシシラン103.9g、テトラエトキシシラン95.4gを、プロピレングリコールモノエチルエーテル204.4gに溶解させた後、スリーワンモーターで攪拌して溶液の温度を55℃に安定させた。次に、シュウ酸0.36gを溶解させたイオン交換水254.2gを1時間かけて溶液に添加した。その後、55℃で3時間反応させた後、プロピレングリコールモノエチルエーテル917.2gを加え反応液を室温まで冷却した。この反応液を固形分濃度が10%となるまで減圧下で濃縮し、ナトリウム含量0.7ppb、カリウム含量1.8ppbおよび鉄含量1.2ppbである膜形成用組成物4を得た。
コンデンサーを備えた石英製フラスコ中で、化合物1としてジビニルジメトキシシラン42.5g、化合物1以外のシラン化合物としてメチルトリメトキシシラン100.4g、テトラメトキシシラン67.3gをプロピレングリコールモノエチルエーテル181.9gに溶解させた。次にイオン交換水247.1gを溶液に加え、室温で1時間攪拌した。その後テトラキス(アセチルアセトナート)チタン0.11gをプロピレングリコールモノエチルエーテル60.6gに溶解したものを添加し、温度50℃で3時間反応させた後、プロピレングリコールモノエチルエーテル979.2gを加え反応液を室温まで冷却した。この反応液を固形分濃度が15%以上となるまで減圧下で濃縮し、アセチルアセトン35.0gを加え、更にプロピレングリコールモノエチルエーテルを固形分濃度10%になるように加え、ナトリウム含量1.7ppb、カリウム含量0.6ppbおよび鉄含量1.8ppbである膜形成用組成物5を得た。
コンデンサーを備えた石英製フラスコ中に、20%水酸化テトラプロピルアンモニウム水溶液35.8g、超純水225.0g、エタノール349.6gを秤取り、40℃で攪拌した。次いで、化合物1としてビニルトリメトキシシラン37.3g、化合物1以外のシラン化合物としてテトラエトキシシラン52.4gを連続的に1時間かけて加えた後、さらに80℃で1時間攪拌した。反応液を室温に冷却後、プロピレングリコールモノプロピルエーテル1149.2gと20%マレイン酸水溶液34.5gを加えた。この反応液を固形分濃度が10%となるまで減圧下で濃縮し、ナトリウム含量2.5ppb、カリウム含量1.6ppbおよび鉄含量1.9ppbである膜形成用組成物6を得た。
コンデンサーを備えた石英製フラスコ中に、20%水酸化テトラプロピルアンモニウム水溶液39.2g、超純水176.8g、エタノール389.2gを秤取り、40℃で攪拌した。次いで、化合物1以外のシラン化合物としてメチルトリメトキシシラン34.5g、テトラエトキシシラン57.3gを連続的に1時間かけて加えた後、さらに80℃で1時間攪拌した。反応液を室温に冷却後、プロピレングリコールモノプロピルエーテル1132.0gと20%マレイン酸水溶液37.8gを加えた。この反応液を固形分濃度が10%となるまで減圧下で濃縮し、ナトリウム含量1.1ppb、カリウム含量1.2ppbおよび鉄含量1.4ppbである膜形成用組成物7を得た。
コンデンサーを備えた石英製フラスコ中に、15%水酸化テトラブチルアンモニウム水溶液37.6g、超純水46.4g、イソプロパノール545.0gを秤取り、40℃で攪拌した。次いで、化合物1としてビニルトリメトキシシラン48.6g、化合物1以外のシラン化合物としてメチルトリメトキシシラン12.7g、テトラエトキシシラン9.7gを連続的に1時間かけて加えた後、さらに80℃で1時間攪拌した。反応液を室温に冷却後、プロピレングリコールモノプロピルエーテル1182.8gと20%マレイン酸水溶液21.3gを加えた。この反応液を固形分濃度が10%となるまで減圧下で濃縮し、ナトリウム含量2.8ppb、カリウム含量1.1ppbおよび鉄含量0.9ppbである膜形成用組成物8を得た。
表1に示す組成物および硬化条件を用いて実施例8〜17,比較例2〜7の有機シリカ系膜を得た。
8インチシリコンウエハ上に、スピンコート法を用いて(1)で得られた膜形成用組成物を塗布し、塗膜をホットプレート上で90℃で1分間、窒素雰囲気下200℃で1分間乾燥した。その後、ホットプレート上で塗膜を加熱しながら紫外線を照射して塗膜の硬化を行い、有機シリカ系膜のサンプルを得た。膜形成用組成物の種類および硬化条件(紫外線の種類,加熱温度,加熱およびUV照射を行うキュア時間)を表1に示す。
実施例8〜17,比較例5では、硬化処理において、加熱と紫外線1の照射を同時に行った。これに対し、比較例2、3、4では、紫外線の照射を行わず、表1に示す条件による熱処理のみを行って塗膜をキュアし、サンプルを得た。
実施例1〜10,比較例4では、硬化処理において、加熱と紫外線1の照射を同時に行った。これに対し、比較例5では、紫外線源1の250nm以下の波長を紫外線カットフィルターでカットした紫外線(以下、「紫外線2」という)を使用して塗膜をキュアし、サンプルを得た。
実施例8〜17,比較例5では、硬化処理において、加熱と紫外線1の照射を同時に行った。これに対し、比較例7では、硬化処理を行わず、乾燥後のサンプルを使用した。
前記4.1.(2)で得られた有機シリカ系膜に関する各種の評価は、次のようにして行った。
0.1Ω・cm以下の抵抗率を有する8インチのN型シリコンウエハ上に、上述の方法で形成された有機シリカ系膜に、蒸着法によりアルミニウム電極パターンを形成させ比誘電率測定用サンプルを作成した。該サンプルを周波数100kHzの周波数で、アリジェント社製、HP16451B電極およびHP4284AプレシジョンLCRメータを用いてCV法により有機シリカ系膜の比誘電率を測定した。
MTS社製超微小硬度計(Nanoindentator XP)にバーコビッチ型圧子を取り付け、連続剛性測定法により、上述の方法で形成された絶縁膜の弾性率を測定した。
デジラボジャパン製FT−IR(FTS3000)によって測定を行った。
固体粉末試料を外径7mmのジルコニア製ローターに詰め、300MHzフーリエ変換NMR分光計(Bruker社製Avance 300)を用いて、13C−NMRをcross-polarization magic angle spining法(CP-MAS)で行った。測定温度30℃、バルス間隔5秒、試料管回転数3000〜7000Hz、観測中心周波数75.48MHz、観測周波数範囲26.46kHz、データポイント16k、積算回数10〜5,000で測定を行った。化学シフトの標準試料として予めグリシンを測定し、カルボニル基のピークを176.03ppmに補正した際のdecoupler frequency offset値を読み取り、各試料の測定時にその値を入力することで補正した。
4.3.1.比誘電率、Δk、弾性率
実施例8〜17および比較例2〜7で得られたシリカ系膜について、比誘電率、弾性率およびΔkを求めた。評価結果を表1に示す。
実施例8〜10および比較例2、7で得られたシリカ系膜について、FT−IRにより、赤外線吸収スペクトルを測定した。
実施例10および比較例2で得られたシリカ系膜について、NMRにより、膜中の組成物の置換基の量を評価した。
Claims (7)
- 下記一般式(A)で表される化合物の群から選ばれた少なくとも1種のシラン化合物(I)と、下記一般式(B)で表される化合物および下記一般式(C)で表される化合物の群から選ばれた少なくとも1種のシラン化合物(II)とを、加水分解、縮合した加水分解縮合物ならびに有機溶媒を含み、
前記シラン化合物(I)および(II)の合計に対して、前記一般式(A)で表される化合物が、5モル%以上50モル%以下である、熱および250nm以下の波長の紫外線を用いて硬化する半導体装置の絶縁膜形成用組成物。
(R9)a−Si−(OR10)4−a・・・(B)
(式中、R9、R10はアルキル基、アリール基、aは0〜3の整数を表す)
R11 b(R12O)3−bSi−(R15)d−Si(OR13)3−cR14 c・・・(C)
[式中、R11〜R14は同一または異なり、それぞれアルキル基、アリール基を示し、bおよびcは同一または異なり、0〜2の数を示し、R15は酸素原子、フェニレン基または−(CH2)m−で表される基(ここで、mは1〜6の整数である)、dは0または1を示す。] - 請求項1において、
前記一般式(B)で表される化合物および前記一般式(C)で表される化合物からなる群から選ばれる2種以上のシラン化合物を用いる、熱および紫外線を用いて硬化する半導体装置の絶縁膜形成用組成物。 - 請求項2において、
前記一般式(B)で表される化合物および前記一般式(C)で表される化合物からなる群から選ばれる2種以上のシラン化合物が、アルキルトリアルコキシシランおよびテトラアルコキシシランである、熱および紫外線を用いて硬化する半導体装置の絶縁膜形成用組成物。 - 請求項1〜3のいずれかにおいて、
紫外線活性を有する反応促進剤を含まない、熱および紫外線を用いて硬化する半導体装置の絶縁膜形成用組成物。 - 請求項4において、
前記紫外線活性を有する反応促進剤は、反応開始剤、酸発生剤、塩基発生剤および紫外線吸収機能を有する増感剤のいずれか、または2種以上の組合せである、熱および紫外線を用いて硬化する半導体装置の絶縁膜形成用組成物。 - 請求項1ないし5のいずれかにおいて、
Na、K、Feの含有量がそれぞれ100ppb以下である、熱および紫外線を用いて硬化する半導体装置の絶縁膜形成用組成物。 - 請求項1ないし6のいずれかに記載された膜形成用組成物を基板に塗布し、塗膜を形成する工程と、
前記塗膜を100〜450℃に加熱した状態で、該塗膜に波長250nm以下の紫外線を照射して硬化処理を行う工程と、
を含む、シリカ系膜の形成方法。
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JP4355939B2 (ja) | 2004-07-23 | 2009-11-04 | Jsr株式会社 | 半導体装置の絶縁膜形成用組成物およびシリカ系膜の形成方法 |
JP2007165914A (ja) * | 2007-01-04 | 2007-06-28 | Fujitsu Ltd | 低誘電率膜形成用組成物 |
JP4437820B2 (ja) * | 2007-01-04 | 2010-03-24 | 富士通マイクロエレクトロニクス株式会社 | 低誘電率膜の製造方法 |
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- 2005-07-21 KR KR1020050066164A patent/KR100709644B1/ko active IP Right Grant
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US7291567B2 (en) | 2007-11-06 |
EP1619226A1 (en) | 2006-01-25 |
JP2006041052A (ja) | 2006-02-09 |
KR20060053974A (ko) | 2006-05-22 |
US20060024980A1 (en) | 2006-02-02 |
TWI277154B (en) | 2007-03-21 |
TW200618111A (en) | 2006-06-01 |
KR100709644B1 (ko) | 2007-04-23 |
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