JPWO2012098828A1 - 低分子化合物、感放射線性組成物、およびレジストパターン形成方法 - Google Patents
低分子化合物、感放射線性組成物、およびレジストパターン形成方法 Download PDFInfo
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- JPWO2012098828A1 JPWO2012098828A1 JP2012553596A JP2012553596A JPWO2012098828A1 JP WO2012098828 A1 JPWO2012098828 A1 JP WO2012098828A1 JP 2012553596 A JP2012553596 A JP 2012553596A JP 2012553596 A JP2012553596 A JP 2012553596A JP WO2012098828 A1 JPWO2012098828 A1 JP WO2012098828A1
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- 238000002411 thermogravimetry Methods 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- IZBIRHQNPWSIET-UHFFFAOYSA-M trifluoromethanesulfonate;tris(4-fluorophenyl)sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(F)=CC=C1[S+](C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 IZBIRHQNPWSIET-UHFFFAOYSA-M 0.000 description 1
- OXWFVYDECNDRMT-UHFFFAOYSA-M trifluoromethanesulfonate;tris(4-methoxyphenyl)sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC)=CC=C1[S+](C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 OXWFVYDECNDRMT-UHFFFAOYSA-M 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
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- KOFQUBYAUWJFIT-UHFFFAOYSA-M triphenylsulfanium;hydroxide Chemical compound [OH-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 KOFQUBYAUWJFIT-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1785—Unsaturated ethers containing hydroxy or O-metal groups having more than one ether bound
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Materials For Photolithography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
しかしながら、高分子系レジストは分子量が1万〜10万程度と大きく、分子量分布も広いため、高分子系レジストを用いるリソグラフィでは、微細パターン表面にラフネスが生じ、パターン寸法を制御することが困難となり、歩留まりが低下する。従って、従来の高分子系レジスト材料を用いるリソグラフィでは微細化に限界がある。より微細なパターンを作製するために、種々の低分子量レジスト材料が開示されている。
低分子量レジスト材料の候補として、低分子量環状ポリフェノール化合物を主成分として用いるアルカリ現像型のネガ型感放射線性組成物(特許文献3および非特許文献1参照)が提案されている。
すなわち、本発明はつぎの通りである。
1.下記式(1)で表される低分子化合物(B)。
3.さらに、溶媒を含む第2項記載の感放射線性組成物。
4.前記低分子化合物(B)を含む固形成分1〜80重量%および前記溶媒20〜99重量%からなる第2項記載の感放射線性組成物。
5.さらに、レジスト用基材(A)を、固形成分全重量の50〜99.999重量%の範囲で含む第2項記載の感放射線性組成物。
6.さらに、可視光線、紫外線、エキシマレーザー、電子線、極端紫外線(EUV)、X線、およびイオンビームからなる群から選ばれるいずれかの放射線の照射により直接的又は間接的に酸を発生する酸発生剤(C)を含む第2項記載の感放射線性組成物。
7.さらに、酸架橋剤(G)を含む第2項記載の感放射線性組成物。
8.さらに、酸拡散制御剤(E)を含む第2項記載の感放射線性組成物。
9.前記固形成分が、低分子化合物(B)/レジスト用基材(A)/酸発生剤(C)/酸架橋剤(G)/酸拡散制御剤(E)/任意成分(F))を、固形成分基準の重量%で、0.5〜99.989/0〜99.489/0.001〜50/0〜50/0.01〜50/0〜50含有する第8項記載の感放射線性組成物。
10.スピンコートによって、アモルファス膜の形成に用いられる第2項記載の感放射線性組成物。
11.前記アモルファス膜の、23℃における2.38重量%テトラメチルアンモニウムヒドロキシド水溶液に対する溶解速度が10Å/sec以上である第10項記載の感放射線性組成物。
12.前記アモルファス膜に、KrFエキシマレーザー、極端紫外線、電子線又はX線を照射した部分、又は、照射後、さらに20〜250℃で加熱した部分についての、2.38重量%テトラメチルアンモニウムヒドロキシド水溶液に対する溶解速度が、5Å/sec以下である第10項記載の感放射線性組成物。
13.レジスト用基材(A)が下記式(2)で示される化合物である、第5項記載の感放射線性組成物。
14.第2〜13項のいずれかに記載の感放射線性組成物を用いて、基板上にレジスト膜を形成する工程、前記レジスト膜を露光する工程、および前記レジスト膜を現像してレジストパターンを形成する工程を含むレジストパターン形成方法。
[低分子化合物]
本発明は、架橋剤及びレジスト材料として有用な低分子化合物に関する。ここで、本発明の低分子化合物とは、分子量が5000以下の化合物のことをいう。
本発明の低分子化合物は、下記式(1)で表される。
本発明は、前記した式(1−1)で示される低分子化合物(B)と溶媒とを含む感放射線性組成物に関する。
また、本発明は、低分子化合物(B)を含む固形成分1〜80重量%および溶媒20〜99重量%からなる感放射線性組成物であることが好ましく、さらに該混合物が固形成分全重量の50〜99.999重量%である感放射線性組成物であることが好ましい。
上記酸発生剤(C)は、単独で、または2種以上を使用することができる。
本発明の感放射線性組成物において酸架橋剤(G)は、アルコキシアルキル化ウレア化合物もしくはその樹脂、またはアルコキシアルキル化グリコールウリル化合物もしくはその樹脂が好ましい。特に好ましい酸架橋剤(G)としては、下記式(6)で示される化合物及びアルコキシメチル化メラミン化合物を挙げることができる(酸架橋剤(G1))。
前記酸架橋剤(G1)は、例えば尿素化合物またはグリコールウリル化合物、およびホルマリンを縮合反応させてメチロール基を導入した後、さらにメチルアルコール、エチルアルコール、プロピルアルコール、ブチルアルコール等の低級アルコール類でエーテル化し、次いで反応液を冷却して析出する化合物またはその樹脂を回収することで得られる。また前記酸架橋剤(G1)は、CYMEL(商品名、三井サイアナミッド製)、ニカラック(三和ケミカル(株)製)のような市販品としても入手することができる。
アルコキシメチル基を有するフェノール誘導体は、対応するヒドロキシメチル基を有するフェノール誘導体とアルコールを酸触媒下で反応させることによって得ることができる。この際、樹脂化やゲル化を防ぐために、反応温度を100℃以下で行うことが好ましい。具体的には、EP632003A1等に記載されている方法にて合成することができる。
上記酸架橋剤(G3)は、通常、1,3−ジアセチルベンゼン等のアセチル基含有化合物に、CH3MgBr等のグリニヤール試薬を反応させてメチル化した後、加水分解する方法や、1,3−ジイソプロピルベンゼン等のイソプロピル基含有化合物を酸素等で酸化して過酸化物を生成させた後、還元する方法により得ることができる。
全酸架橋剤成分において、上記アルコキシメチル化メラミン化合物及び/又は(7−1)〜(7−3)で示される化合物が50〜99重量%、好ましくは60〜99重量%、より好ましくは70〜98重量%、更に好ましくは80〜97重量%であることが好ましい。アルコキシメチル化メラミン化合物及び/又は(7−1)〜(7−3)で示される化合物を全酸架橋剤成分の50重量%以上とすることにより、解像度を向上させることができるので好ましく、99重量%以下とすることにより、パターン断面形状として矩形状の断面形状とし易いので好ましい。
上記酸拡散制御剤としては、例えば、含窒素有機化合物や、露光により分解する塩基性化合物等が挙げられる。上記含窒素有機化合物としては、例えば、下記一般式(8):
上記アミド基含有化合物として具体的には、例えば、ホルムアミド、N−メチルホルムアミド、N,N−ジメチルホルムアミド、アセトアミド、N−メチルアセトアミド、N,N−ジメチルアセトアミド、プロピオンアミド、ベンズアミド、ピロリドン、N−メチルピロリドン等を挙げることができる。
低分子量溶解促進剤は、化合物のアルカリ等の現像液に対する溶解性が低すぎる場合に、その溶解性を高めて、現像時の感放射線性化合物の溶解速度を適度に増大させる作用を有する成分であり、本発明の効果を損なわない範囲で使用することができる。前記溶解促進剤としては、例えば、低分子量のフェノール性化合物を挙げることができ、例えば、ビスフェノール類、トリス(ヒドロキシフェニル)メタン等を挙げることができる。これらの溶解促進剤は、単独でまたは2種以上を混合して使用することができる。溶解促進剤の配合量は、使用する式(1)で示される低分子化合物の種類に応じて適宜調節されるが、式(1)で示される低分子化合物100重量部当たり、0〜100重量部が好ましく、好ましくは0〜30重量部であり、より好ましくは0〜10重量部、更に好ましくは0〜2重量部である。
溶解制御剤は、式(1)で示される化合物(B)がアルカリ等の現像液に対する溶解性が高すぎる場合に、その溶解性を制御して現像時の溶解速度を適度に減少させる作用を有する成分である。このような溶解制御剤としては、レジスト被膜の焼成、放射線照射、現像等の工程において化学変化しないものが好ましい。
溶解制御剤としては、例えば、ナフタレン、フェナントレン、アントラセン、アセナフテン等の芳香族炭化水素類;アセトフェノン、ベンゾフェノン、フェニルナフチルケトン等のケトン類;メチルフェニルスルホン、ジフェニルスルホン、ジナフチルスルホン等のスルホン類等を挙げることができる。これらの溶解制御剤は、単独でまたは2種以上を使用することができる。
溶解制御剤の配合量は、使用する化合物の種類に応じて適宜調節されるが、式(1)で示される化合物100重量部当たり、0〜100重量部が好ましく、好ましくは0〜30重量部であり、より好ましくは0〜10重量部、更に好ましくは0〜2重量部である。
増感剤は、照射された放射線のエネルギーを吸収して、そのエネルギーを酸発生剤(C)に伝達し、それにより酸の生成量を増加する作用を有し、レジストの見掛けの感度を向上させる成分である。このような増感剤としては、例えば、ベンゾフェノン類、ビアセチル類、ピレン類、フェノチアジン類、フルオレン類等を挙げることができるが、特に限定はされない。
これらの増感剤は、単独でまたは2種以上を使用することができる。増感剤の配合量は、使用する化合物の種類に応じて適宜調節されるが、レジスト用基材(A)100重量部当たり、0〜100重量部が好ましく、好ましくは0〜30重量部であり、より好ましくは0〜10重量部、更に好ましくは0〜2重量部である。
界面活性剤は、感放射線性組成物の塗布性やストリエーション、レジストの現像性等を改良する作用を有する成分である。このような界面活性剤は、アニオン系、カチオン系、ノニオン系あるいは両性のいずれでもよい。好ましい界面活性剤はノニオン系界面活性剤である。ノニオン系界面活性剤は、感放射線性組成物の製造に用いる溶媒との親和性がよく、より効果がある。ノニオン系界面活性剤の例としては、ポリオキシエチレン高級アルキルエーテル類、ポリオキシエチレン高級アルキルフェニルエーテル類、ポリエチレングリコールの高級脂肪酸ジエステル類等が挙げられるが、特に限定はされない。市販品としては、以下商品名で、エフトップ(ジェムコ社製)、メガファック(大日本インキ化学工業社製)、フロラード(住友スリーエム社製)、アサヒガード、サーフロン(以上、旭硝子社製)、ペポール(東邦化学工業社製)、KP(信越化学工業社製)、ポリフロー(共栄社油脂化学工業社製)等を挙げることができる。
界面活性剤の配合量は、使用するレジスト用基材(A)の種類に応じて適宜調節されるが、レジスト用基材(A)100重量部当たり、0〜100重量部が好ましく、好ましくは0〜30重量部であり、より好ましくは0〜10重量部、更に好ましくは0〜2重量部である。
感度劣化防止またはレジストパターン形状、引き置き安定性等の向上の目的で、さらに任意の成分として、有機カルボン酸またはリンのオキソ酸もしくはその誘導体を含有させることができる。なお、酸拡散制御剤と併用することも出来るし、単独で用いても良い。有機カルボン酸としては、例えば、マロン酸、クエン酸、リンゴ酸、コハク酸、安息香酸、サリチル酸などが好適である。リンのオキソ酸もしくはその誘導体としては、リン酸、リン酸ジ−n−ブチルエステル、リン酸ジフェニルエステルなどのリン酸またはそれらのエステルなどの誘導体、ホスホン酸、ホスホン酸ジメチルエステル、ホスホン酸ジ−n−ブチルエステル、フェニルホスホン酸、ホスホン酸ジフェニルエステル、ホスホン酸ジベンジルエステルなどのホスホン酸またはそれらのエステルなどの誘導体、ホスフィン酸、フェニルホスフィン酸などのホスフィン酸およびそれらのエステルなどの誘導体が挙げられ、これらの中で特にホスホン酸が好ましい。
有機カルボン酸またはリンのオキソ酸もしくはその誘導体は、単独でまたは2種以上を使用することができる。有機カルボン酸またはリンのオキソ酸もしくはその誘導体の配合量は、使用する化合物の種類に応じて適宜調節されるが、レジスト用基材(A)100重量部当たり、0〜100重量部が好ましく、好ましくは0〜30重量部であり、より好ましくは0〜10重量部、更に好ましくは0〜2重量部である。
更に、本発明の感放射線性組成物には、本発明の目的を阻害しない範囲で、必要に応じて、上記溶解制御剤、増感剤、及び界面活性剤以外の添加剤を1種又は2種以上配合することができる。そのような添加剤としては、例えば、染料、顔料、及び接着助剤等が挙げられる。例えば、染料又は顔料を配合すると、露光部の潜像を可視化させて、露光時のハレーションの影響を緩和できるので好ましい。また、接着助剤を配合すると、基板との接着性を改善することができるので好ましい。更に、他の添加剤としては、ハレーション防止剤、保存安定剤、消泡剤、形状改良剤等、具体的には4−ヒドロキシ−4’−メチルカルコン等を挙げることができる。
より好ましくは
0.5〜99.989/50〜99.999/0.001〜50/0〜40/0.01〜5/0〜15、
さらに好ましくは
0.5〜99.989/60〜70/10〜25/0〜30/0.01〜3/0〜1
特に好ましくは
0.5〜99.989/60〜70/10〜25/0〜20/0.01〜3/0である。上記配合にすると、感度、解像度、アルカリ現像性等の性能に優れる。
本発明は、上記本発明の感放射線性組成物を用いて、基板上にレジスト膜を形成する工程、前記レジスト膜を露光する工程、および前記レジスト膜を現像してレジストパターンを形成する工程を含むレジストパターン形成方法に関する。本発明のレジストパターンは多層レジストプロセスにおける上層レジストとして形成することもできる。
レジストパターンを形成するには、従来公知の基板上に前記本発明の感放射線性組成物を、回転塗布、流延塗布、ロール塗布等の塗布手段によって塗布することによりレジスト膜を形成する。従来公知の基板とは、特に限定されず、例えば、電子部品用の基板や、これに所定の配線パターンが形成されたもの等を例示することができる。より具体的には、シリコンウェハー、銅、クロム、鉄、アルミニウム等の金属製の基板や、ガラス基板等が挙げられる。配線パターンの材料としては、例えば銅、アルミニウム、ニッケル、金等が挙げられる。また必要に応じて、前述基板上に無機系および/または有機系の膜が設けられたものであってもよい。無機系の膜としては、無機反射防止膜(無機BARC)が挙げられる。有機系の膜としては、有機反射防止膜(有機BARC)が挙げられる。ヘキサメチレンジシラザン等による表面処理を行ってもよい。
次いで、必要に応じ、塗布した基板を加熱する。加熱条件は、感放射線性組成物の配合組成等により変わるが、20〜250℃が好ましく、より好ましくは20〜150℃である。加熱することによって、レジストの基板に対する密着性が向上する場合があり好ましい。次いで、可視光線、紫外線、エキシマレーザー、電子線、極端紫外線(EUV)、X線、およびイオンビームからなる群から選ばれるいずれかの放射線により、レジスト膜を所望のパターンに露光する。露光条件等は、感放射線性組成物の配合組成等に応じて適宜選定される。本発明においては、露光における高精度の微細パターンを安定して形成するために、放射線照射後に加熱するのが好ましい。加熱条件は、感放射線性レジスト組成物の配合組成等により変わるが、20〜250℃が好ましく、より好ましくは20〜150℃である。
また、前記アルカリ現像液には、メタノール、エタノール、イソプロピルアルコールなどのアルコール類や前記界面活性剤を適量添加することもできる。これらのうちイソプロピルアルコールを10〜30質量%添加することが特に好ましい。これにより、レジストに対する現像液の濡れ性を高めることが出来るので好ましい。なお、このようなアルカリ性水溶液からなる現像液を用いた場合は、一般に、現像後、水で洗浄する。
レジストパターンを形成した後、めっきを行うことも出来る。上記めっき法としては、例えば、銅めっき、はんだめっき、ニッケルめっき、金めっきなどがある。
エッチング後の残存レジストパターンは有機溶剤や現像に用いたアルカリ水溶液より強アルカリ性の水溶液で剥離することが出来る。上記有機溶剤として、PGMEA(プロピレングリコールモノメチルエーテルアセテート),PGME(プロピレングリコールモノメチルエーテル),EL(乳酸エチル)等が挙げられ、強アルカリ水溶液としては、例えば1〜20質量%の水酸化ナトリウム水溶液や1〜20質量%の水酸化カリウム水溶液が挙げられる。上記剥離方法としては、例えば、浸漬方法、スプレイ方式等が挙げられる。またレジストパターンが形成された配線基板は、多層配線基板でも良く、小径スルーホールを有していても良い。
本発明で得られる配線基板は、レジストパターン形成後、金属を真空中で蒸着し、その後レジストパターンを溶液で溶かす方法、すなわちリフトオフ法により形成することもできる。
反応後、酢酸エチルを投入し、有機相を1N HClで洗浄、水洗、食塩水洗浄し、乾燥させた。エバポレーションにより濃縮し、カラム精製及び乾燥後、目的生成物(以下、BIP−PHBZ−6M)(3.2g、収率34%) を得た。
この化合物をLC−MSで分析した結果、目的物の分子量473を示した。また得られた生成物の重ジメチルスルホキシド溶媒中での1H−NMRのケミカルシフト値(δppm ,TMS基準)は4.5(s,18H)、5.3(s,1H)、6.9(s,6H)、8.4(s,3H)であった。
反応終了後、室温まで冷却し、炭酸カリウム0.2g を加え、エバポレーションにより濃縮し、酢酸エチル30mL を加えた。水洗した後、乾燥させ目的生成物(以下、BIP−PHBZ−6MX)(2.13g、収率91%)を得た。
この化合物をLC−MSで分析した結果、目的物の分子量557を示した。また得られた生成物の重ジメチルスルホキシド溶媒中での1H−NMRのケミカルシフト値(δppm ,TMS基準)は3.2(s,18H)、4.4(s,12H)、5.3(s,1H)、6.9(s,6H)、8.4(s,3H)であった。
反応後、酢酸エチルを投入し、有機相を1N HClで洗浄、水洗、食塩水洗浄し、乾燥させた。エバポレーションにより濃縮し、カラム精製及び乾燥後、目的生成物(以下、TEP−DF−8M)(2.8g、収率29%) を得た。
この化合物をLC−MSで分析した結果、目的物の分子量639を示した。また得られた生成物の重ジメチルスルホキシド溶媒中での1H−NMRのケミカルシフト値(δppm ,TMS基準)は4.4(s,16H)、4.7(d,2H)、5.2(s,8H)、7.1(s,8H)、8.2(s,4H)であった。
反応終了後、室温まで冷却し、炭酸カリウム0.2g を加え、エバポレーションにより濃縮し、酢酸エチル30mL を加えた。水洗した後、乾燥させ目的生成物(以下、TEP−DF−8MX)(2.11g、収率88%)を得た。
この化合物をLC−MSで分析した結果、目的物の分子量751を示した。また得られた生成物の重ジメチルスルホキシド溶媒中での1H−NMRのケミカルシフト値(δppm ,TMS基準)は3.2(s,24H)、4.3(s,16H)、4.7(d,2H)、7.2(s,8H)、8.0(s,4H)であった。
十分乾燥し、窒素置換した滴下漏斗、ジム・ロート氏冷却管、温度計、攪拌翼を設置した四つ口フラスコ(2000mL)に、窒素気流下で、関東化学社製レゾルシノール(120g、1.09mol)と、脱水エタノール(1.36L)、濃塩酸(35%)168mLを投入し、エタノール溶液を調製した。次いで4−シクロヘキシルベンズアルデヒド(196g,1.04mol)を混合し、滴下漏斗により10分かけて滴下した後、この溶液を攪拌しながらマントルヒーターで80℃まで加熱した。引き続き80℃で5時間攪拌した。反応終了後、放冷し室温に到達させた。目的粗結晶が生成し、反応後これを濾別し、蒸留水1000mLを加えた。これを濾別し、粗結晶を蒸留水1000mlで6回洗浄し、濾別、真空乾燥させることにより、目的生成物(以下、CR−6Aと示す)(278g、収率91%)を得た。
この化合物の構造は、LC−MSで分析した結果、目的物の分子量1122を示した。また重ジメチルスルホキシド溶媒中での1H−NMRのケミカルシフト値(δppm,TMS基準)は0.8〜1.9(m,44H)、5.5〜5.6(d,4H)、6.0〜6.8(m,24H)、8.4〜8.5(m,8H)であった。
(1)化合物の安全溶媒溶解度試験
合成実施例1および2にて合成したBIP‐PHBZ−6M、BIP‐PHBZ−6MXについて、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)、プロピレングリコールモノメチルエーテル(PGME)、およびシクロヘキサノン(CHN)への溶解量を評価した。結果を第1表に示す。
A:1.0wt% ≦ 溶解量
B:0.1wt% ≦ 溶解量 < 1.0wt%
C:溶解量 < 0.1wt%
(2)パターニング試験
第2表記載の成分を調合し、均一溶液としたのち、孔径0.1μmのテフロン(登録商標)製メンブランフィルターで濾過して、感放射線性組成物を調製し、各々について以下の評価を行った。結果を第3表に示す。
レジストを清浄なシリコンウェハー上に回転塗布した後、オーブン中で露光前ベーク(PB)して、厚さ60nmのレジスト膜を形成した。該レジスト膜を電子線描画装置(ELS−7500,(株)エリオニクス社製)を用いて、50nm間隔の1:1のラインアンドスペース設定の電子線を照射した。照射後に、それぞれ所定の温度で、90秒間加熱し、2.38重量%TMAH水溶液に60秒間現像を行った。その後、水で30秒間洗浄し、乾燥して、ネガ型のレジストパターンを形成した。得られたラインアンドスペースを走査型電子顕微鏡((株)日立ハイテクノロジー製S−4800)により観察した。またその際のドーズ量(μC/cm2)を感度とした。
得られた50nm間隔の1:1のラインアンドスペースの断面写真を走査型電子顕微鏡((株)日立ハイテクノロジー製S−4800)により観察し、評価した。
A:矩形パターン(良好なパターン)
B:矩形ではないパターン(良好でないパターン)
50nm間隔の1:1のラインアンドスペースの長さ方向(0.75μm)の任意の300点において、日立半導体用SEM ターミナルPC V5オフライン測長ソフトウェア((株)日立サイエンスシステムズ製)を用いて、エッジと基準線との距離を測定した。測定結果から標準偏差(3σ)を算出した。
A:LER(3σ)≦7.0nm (良好なLER)
B:7.0nm<LER(3σ) (良好でないLER)
感度について以下のように記載した。
A:ドーズ量<50μC/cm2
B:50μC/cm2≦ドーズ量
P−1:トリフェニルベンゼンスルホニウム トリフルオロメタンスルホネート(みどり化学(株))
(G)酸架橋剤
C−1 ニカラックMX−270(三和ケミカル(株))
(E)酸拡散制御剤
Q−1 トリオクチルアミン(東京化成工業(株))
溶媒
S−1 プロピレングリコールモノメチルエーテル(東京化成工業(株))
Claims (14)
- 請求項1に記載の低分子化合物(B)を含む感放射線性組成物。
- さらに、溶媒を含む請求項2記載の感放射線性組成物。
- 前記低分子化合物(B)を含む固形成分1〜80重量%および前記溶媒20〜99重量%からなる請求項2記載の感放射線性組成物。
- さらに、レジスト用基材(A)を、固形成分全重量の50〜99.999重量%の範囲で含む請求項2記載の感放射線性組成物。
- さらに、可視光線、紫外線、エキシマレーザー、電子線、極端紫外線(EUV)、X線、およびイオンビームからなる群から選ばれるいずれかの放射線の照射により直接的又は間接的に酸を発生する酸発生剤(C)を含む請求項2記載の感放射線性組成物。
- さらに、酸架橋剤(G)を含む請求項2記載の感放射線性組成物。
- さらに、酸拡散制御剤(E)を含む請求項2記載の感放射線性組成物。
- 前記固形成分が、低分子化合物(B)/レジスト用基材(A)/酸発生剤(C)/酸架橋剤(G)/酸拡散制御剤(E)/任意成分(F))を、固形成分基準の重量%で、0.5〜99.989/0〜99.489/0.001〜50/0〜50/0.01〜50/0〜50含有する請求項8記載の感放射線性組成物。
- スピンコートによって、アモルファス膜の形成に用いられる請求項2記載の感放射線性組成物。
- 前記アモルファス膜の、23℃における2.38重量%テトラメチルアンモニウムヒドロキシド水溶液に対する溶解速度が、10Å/sec以上である請求項10記載の感放射線性組成物。
- 前記アモルファス膜に、KrFエキシマレーザー、極端紫外線、電子線又はX線を照射した部分、又は、照射後、さらに20〜250℃で加熱した部分についての、2.38重量%テトラメチルアンモニウムヒドロキシド水溶液に対する溶解速度が、5Å/sec以下である請求項10記載の感放射線性組成物。
- 前記レジスト用基材(A)が下記式(2)で示される化合物である請求項5記載の感放射線性組成物。
- 請求項2〜13のいずれかに記載の感放射線性組成物を用いて、基板上にレジスト膜を形成する工程、前記レジスト膜を露光する工程、および前記レジスト膜を現像してレジストパターンを形成する工程を含むレジストパターン形成方法。
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