CN115885217A - 负型抗蚀剂膜层叠体及图案形成方法 - Google Patents
负型抗蚀剂膜层叠体及图案形成方法 Download PDFInfo
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- CN115885217A CN115885217A CN202180040680.8A CN202180040680A CN115885217A CN 115885217 A CN115885217 A CN 115885217A CN 202180040680 A CN202180040680 A CN 202180040680A CN 115885217 A CN115885217 A CN 115885217A
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- resist film
- negative resist
- acid
- oxime
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- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
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Abstract
本发明提供负型抗蚀剂膜层叠体,其具备作为第一支承体的热塑性膜和负型抗蚀剂膜,其中,所述负型抗蚀剂膜包含:(A)具有酚羟基的碱可溶性树脂、(B)包含聚酯的增塑剂、(C)光致产酸剂、(D)在1分子中包含平均4个以上的环氧基的环氧化合物、和(E)苯并三唑化合物和/或咪唑化合物。
Description
技术领域
本发明涉及负型抗蚀剂膜层叠体及图案形成方法。
背景技术
通常,在半导体制造工艺中,在膜、片、金属基板、陶瓷基板等支承体上使用抗蚀剂材料形成抗蚀剂膜,但该支承体的表面随着电路形成而形成台阶高差,因此对半导体制造工艺后半段的工艺中使用的抗蚀剂材料要求在具有台阶高差的表面上的均匀的涂膜性、不产生空隙等缺陷。在这样的不均匀的台阶高差支承体上的表面涂布液态的抗蚀剂材料时,难以得到均匀的涂膜的厚度,在台阶高差附近容易产生空隙,因此难以用液态抗蚀剂材料满足上述的要求,抗蚀剂膜适合。
而且,对于满足这样的要求的负型抗蚀剂膜,在专利文献1中记载了使用有机硅氧烷系的树脂来保持可挠性的膜材料,关于显影,是采用有机溶剂的显影,由于与碱水溶液显影不同,因此具有需要改变显影时的设备的问题。另外,在专利文献2中,记载了抑制了在台阶高差基板上产生空隙的负型抗蚀剂膜,但存在固化后被膜的耐化学品性低的问题,期望其改善。
现有技术文献
专利文献
专利文献1:日本特开2011-145664号公报
专利文献2:日本特开2019-128438号公报
发明内容
发明所要解决的课题
本发明是鉴于上述情况而完成的,其目的在于提供负型抗蚀剂膜层叠体以及图案形成方法,该负型抗蚀剂膜层叠体能够在具有台阶高差的支承体不产生空隙地转印负型抗蚀剂膜,固化后的耐化学品性优异。
用于解决课题的手段
本发明人为了实现上述目的而进行了深入研究,结果发现,具备热塑性膜、和包含具有酚羟基的碱可溶性树脂、包含聚酯的增塑剂、光致产酸剂、在1分子中含有平均4个以上的环氧基的环氧化合物、苯并三唑化合物和/或咪唑化合物的负型抗蚀剂膜的负型抗蚀剂膜层叠体能够解决上述课题,完成了本发明。
即,本发明提供下述负型抗蚀剂膜层叠体及图案形成方法。
1.负型抗蚀剂膜层叠体,其具备作为第一支承体的热塑性膜和负型抗蚀剂膜,所述负型抗蚀剂膜包含:
(A)具有酚羟基的碱可溶性树脂,
(B)包含聚酯的增塑剂,
(C)光致产酸剂,
(D)在1分子中含有平均4个以上的环氧基的环氧化合物,以及
(E)苯并三唑化合物和/或咪唑化合物。
2.根据1所述的层叠体,其中,所述聚酯是具有2~6个羧基的多元羧酸系聚酯。
3.图案形成方法,其包括:
(1)在第二支承体上转印根据1或2所述的层叠体的负型抗蚀剂膜的工序,
(2)对所述抗蚀剂膜进行曝光的工序,和
(3)利用碱水溶液对所述抗蚀剂膜进行显影的工序。
4.根据3所述的图案形成方法,其中,在工序(1)中,转印后进行加热处理。
5.根据3或4所述的图案形成方法,其中,在工序(2)中,曝光后进行加热处理。
发明的效果
根据本发明的负型抗蚀剂膜层叠体,即使是具有台阶高差的支承体,也能够在其上不产生空隙地转印负型抗蚀剂膜,固化后能够形成具有高耐化学品性的图案。
具体实施方式
[负型抗蚀剂膜层叠体]
本发明的负型抗蚀剂膜层叠体具备作为第一支承体的热塑性膜和可转印到第二支承体上的负型抗蚀剂膜。
[热塑性膜]
作为第一支承体的热塑性膜由于要成为脱模基材,因此,只要在不损害所述负型抗蚀剂膜的形态的情况下能够从所述负型抗蚀剂膜剥离,就没有特别限定。作为这样的膜,可以使用由单一的聚合物膜构成的单层膜或将多个聚合物膜层叠而成的多层膜。具体而言,可举出尼龙膜、聚乙烯(PE)膜、聚对苯二甲酸乙二醇酯(PET)膜、聚萘二甲酸乙二醇酯膜、聚苯硫醚(PPS)膜、聚丙烯(PP)膜、聚苯乙烯膜、聚甲基戊烯(TPX)膜、聚碳酸酯膜、含氟膜、特殊聚乙烯醇(PVA)膜、实施了脱模处理的聚酯膜等塑料膜等。
其中,作为第一支承体,优选具有适度的可挠性、机械强度和耐热性的PET膜、PP膜。另外,对于这些膜,也可以是进行了电晕处理、涂布了剥离剂这样的各种处理的膜。作为上述热塑性膜,可以使用市售品,例如可列举:Cerapeel(注册商标)WZ(RX)、BX8(R)(东丽膜加工(株)制造)、E7302、E7304(东洋纺(株)制造)、Purex(注册商标)G31、G71T1(帝人FILMSOLUTION(株)制造)、PET38×1-A3、PET38×1-V8、PET38×1-X08(ニッパ(株)制造)等。应予说明,在本发明中,可挠性意指膜在常温常压下显示柔软性、变形时不产生裂纹的性质。
[负型抗蚀剂膜]
上述负型抗蚀剂膜包含:(A)具有酚羟基的碱可溶性树脂、(B)包含聚酯的增塑剂、(C)光致产酸剂、(D)在1分子中包含平均4个以上的环氧基的环氧化合物、以及(E)苯并三唑化合物和/或咪唑化合物。
[(A)具有酚羟基的碱可溶性树脂]
作为上述负型抗蚀剂膜的基础树脂使用的具有酚羟基的碱可溶性树脂,可举出将酚类与醛类在酸催化剂存在下缩聚而成的酚醛清漆树脂、聚羟基苯乙烯树脂、羟基苯乙烯与其他自由基聚合性单体(丙烯酸甲酯、甲基丙烯酸甲酯等丙烯酸系单体、苯乙烯)共聚而成的树脂等。其中,优选酚醛清漆树脂。
作为上述酚类,可以举出苯酚;间甲酚、邻甲酚、对甲酚、2,3-二甲苯酚、2,5-二甲苯酚、3,5-二甲苯酚、3,4-二甲苯酚等二甲苯酚类;间乙基苯酚、对乙基苯酚、邻乙基苯酚、2,3,5-三甲基苯酚、2,3,5-三乙基苯酚、4-叔丁基苯酚、3-叔丁基苯酚、2-叔丁基苯酚、2-叔丁基-4-甲基苯酚、2-叔丁基-5-甲基苯酚、6-叔丁基-3-甲基苯酚等烷基酚类;对甲氧基苯酚、间甲氧基苯酚、对乙氧基苯酚、间乙氧基苯酚、对丙氧基苯酚、间丙氧基苯酚等烷氧基苯酚类;邻异丙烯基苯酚、对异丙烯基苯酚、2-甲基-4-异丙烯基苯酚、2-乙基-4-异丙烯基苯酚等异丙烯基苯酚类;4,4'-二羟基联苯、双酚A、苯基苯酚、间苯二酚、对苯二酚、连苯三酚等多羟基酚类;α-萘酚、β-萘酚、二羟基萘等羟基萘类等。其中,优选以苯酚、邻甲酚、间甲酚、对甲酚、2,3-二甲苯酚、2,5-二甲苯酚和/或3,5-二甲苯酚作为原料,更优选以间甲酚和/或对甲酚为原料。
作为上述醛类,可以举出甲醛、多聚甲醛、三噁烷、乙醛、丙醛、丁醛、三甲基乙醛、丙烯醛、巴豆醛、环己基甲醛、糠醛、呋喃基丙烯醛、苯甲醛、对苯二甲醛、苯乙醛、α-苯基丙醛、β-苯基丙醛、邻羟基苯甲醛、间羟基苯甲醛、对羟基苯甲醛、邻甲基苯甲醛、间甲基苯甲醛、对甲基苯甲醛、邻氯苯甲醛、间氯苯甲醛、对氯苯甲醛等。它们可以单独使用1种,也可以组合2种以上使用。这些醛类中,从容易获得考虑,优选甲醛。
上述酚醛清漆树脂,作为原料的酚类,优选在该酚类中使用40摩尔%以上的对甲酚而得到的酚醛清漆树脂,更优选使用45摩尔%以上而得到的酚醛清漆树脂。在这种情况下,对甲酚的使用量的上限为该酚类中的100摩尔%,在除了对甲酚以外还使用其他酚类的情况下,对甲酚的使用量的上限优选为80摩尔%,更优选为70摩尔%。作为上述其他酚类,优选间甲酚、2,5-二甲苯酚、3,5-二甲苯酚,更优选间甲酚。
(A)成分的树脂的重均分子量(Mw)优选为3000~50000,更优选为5000~30000。应予说明,在本发明中,Mw是使用四氢呋喃作为溶剂的采用凝胶渗透色谱法的聚苯乙烯换算测定值。
(A)成分的树脂可以单独使用1种,也可以组合2种以上使用。
[(B)增塑剂]
(B)成分的增塑剂包含聚酯。上述聚酯是多元羧酸和多元醇的缩合物、或者多元羧酸酐和多元醇的缩合物。
作为上述多元羧酸,优选具有2~6个羧基的多元羧酸,具体而言,可以举出草酸、琥珀酸、丙二酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸、癸二酸、巴西基酸、甲基丙二酸、柠康酸、富马酸、马来酸、甲基马来酸、中康酸、戊烯二酸、衣康酸、烯丙基丙二酸、芸康酸、粘康酸、2-丁炔二酸、乌头酸、苹果酸、酒石酸、葡萄酸、柠檬酸、氧代丙二酸、氧代琥珀酸、硫代苹果酸、谷氨酸、乙二胺四乙酸、1,2-环丙烷二羧酸、古柯间二酸、樟脑酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、苯基琥珀酸、2-(3-羧基苯基)-2-氧代乙酸、袂康酸、环丁烷二羧酸等。进而,可以使用它们的酸酐。其中,优选二元羧酸。上述多元羧酸可以单独使用1种,也可以组合使用2种以上。
另外,作为多元醇,可以举出1,2-丙二醇、1,3-丙二醇、1,2-丁二醇、1,3-丁二醇、3-甲基-1,3-丁二醇、1,4-丁二醇、1,4-环己烷二甲醇、1,2-戊二醇、1,3-戊二醇、1,5-戊二醇、1,6-己二醇、2-甲基-2,4-戊二醇、3-甲基-1,5-戊二醇、乙二醇、丙二醇、新戊二醇、甘油、五甘油等。其中,优选二元醇。上述多元醇可以单独使用1种,也可以组合2种以上使用。
使用上述原料,按照公知的方法进行缩聚,从而得到聚酯。原料的使用量可以根据得到的聚合物的分子量适当调整,通常,相对于1摩尔多元羧酸,多元醇为0.5~3摩尔左右。另外,酯化可以是公知的方法,使用硫酸等酸性催化剂、钛化合物、锡化合物、锌化合物、锗化合物、锑化合物等金属,根据需要在150~300℃左右加热,使其缩合反应即可。
作为上述聚酯,可使用市售品,例如,可列举出Polysizer(注册商标)W-2050、W-2310、W-230-H、W-1020-EL、W-1410-EL、W-705(DIC(株)制)、ADK Cizer(注册商标)PN-150、PN-170、PN-230、PN-280、PN-7230、PN-1010、PN-1020、PN-1030、P-200、PN-260、PN-650、PN-7650、PN-1430、HPN--3130、PN-446、PN-7310((株)ADEKA制)、D620、D621、D623、D643、D64、D633、D620N、D623N、D643D、D640A((株)J-Plus制)等。
上述聚酯的Mw优选为700~50000,更优选为1500~45000。如果Mw为上述范围,则显影速度良好,因此优选。
(B)成分为负型抗蚀剂膜的构成成分,因此优选为碱可溶性,特别优选溶解于四甲基氢氧化铵(TMAH)水溶液中。
(B)成分的增塑剂可以只包含所述聚酯,但也可以包含所述聚酯以外的其他增塑剂。作为其他增塑剂,可以使用以往公知的增塑剂。其他增塑剂的含量只要不损害本发明的效果,则没有特别限定。
就(B)成分的含量而言,相对于(A)成分的树脂100质量份,优选为5~100质量份,更优选为10~60质量份,进一步优选为15~50质量份。如果含量在上述范围内,则在将上述负型抗蚀剂膜转印到第二支承体上时不会产生空隙。(B)成分的聚酯可以单独使用1种,也可以将2种以上组合使用。
[(C)光致产酸剂]
作为(C)成分的光致产酸剂,只要是通过高能射线照射产生酸的化合物,则没有特别限定。作为上述高能射线,可以举出紫外线、远紫外线、电子束(EB)等,具体而言,可以举出g射线、h射线、i射线、KrF准分子激光、ArF准分子激光、EB、同步加速器放射光等。
作为优选的光致产酸剂,可以举出锍盐、碘鎓盐、磺酰基重氮甲烷、N-磺酰氧基酰亚胺型光致产酸剂、苯偶姻磺酸酯型光致产酸剂、连苯三酚三磺酸酯型光致产酸剂、硝基苄基磺酸酯型光致产酸剂、砜型光致产酸剂、O-芳基磺酰肟化合物或O-烷基磺酰肟化合物(磺酸肟酯)型光致产酸剂等。
上述锍盐是锍阳离子和磺酸根阴离子的盐。作为上述锍阳离子,可以举出三苯基锍、(4-叔丁氧基苯基)二苯基锍、双(4-叔丁氧基苯基)苯基锍、三(4-叔丁氧基苯基)锍、(3-叔丁氧基苯基)二苯基锍、双(3-叔丁氧基苯基)苯基锍、三(3-叔丁氧基苯基)锍、(3,4-二叔丁氧基苯基)二苯基锍、双(3,4-二叔丁氧基苯基)苯基锍、三(3,4-二叔丁氧基苯基)锍、二苯基(4-硫代苯氧基苯基)锍、(4-叔丁氧基羰基甲氧基苯基)二苯基锍、三(4-叔丁氧基羰基甲氧基苯基)锍、(4-叔丁氧基苯基)双(4-二甲基氨基苯基)锍、三(4-二甲基氨基苯基)锍、2-萘基二苯基锍、二甲基2-萘基锍、4-羟基苯基二甲基锍、4-甲氧基苯基二甲基锍、三甲基锍、2-氧代环己基环己基甲基锍、三萘基锍、三苄基锍等。作为上述磺酸根阴离子,可以举出三氟甲磺酸根、九氟丁磺酸根、十七氟辛磺酸根、2,2,2-三氟乙磺酸根、五氟苯磺酸根、4-三氟甲基苯磺酸根、4-氟苯磺酸根、甲苯磺酸根、苯磺酸根、4-(4-甲苯磺酰氧基)苯磺酸根、萘磺酸根、樟脑磺酸根、辛磺酸根、十二烷基苯磺酸根、丁磺酸根、甲磺酸根等。作为上述锍盐,优选由它们的组合构成。
上述碘鎓盐是碘鎓阳离子和磺酸根阴离子的盐。作为上述碘鎓阳离子,可以举出二苯基碘鎓、双(4-叔丁基苯基)碘鎓、4-叔丁氧基苯基苯基碘鎓、4-甲氧基苯基苯基碘鎓等芳基碘鎓阳离子等。作为上述磺酸根阴离子,可以举出三氟甲磺酸根、九氟丁磺酸根、十七氟辛磺酸根、2,2,2-三氟乙磺酸根、五氟苯磺酸根、4-三氟甲基苯磺酸根、4-氟苯磺酸根、甲苯磺酸根、苯磺酸根、4-(4-甲苯磺酰氧基)苯磺酸根、萘磺酸根、樟脑磺酸根、辛磺酸根、十二烷基苯磺酸根、丁磺酸根、甲磺酸根等。作为上述碘鎓盐,优选由它们的组合构成。
作为上述磺酰基重氮甲烷,可以举出双(乙基磺酰基)重氮甲烷、双(1-甲基丙基磺酰基)重氮甲烷、双(2-甲基丙基磺酰基)重氮甲烷、双(1,1-二甲基乙基磺酰基)重氮甲烷、双(环己基磺酰基)重氮甲烷、双(全氟异丙基磺酰基)重氮甲烷、双(苯基磺酰基)重氮甲烷、双(4-甲基苯基磺酰基)重氮甲烷、双(2,4-二甲基苯基磺酰基)重氮甲烷、双(2-萘基磺酰基)重氮甲烷、4-甲基苯基磺酰基苯甲酰基重氮甲烷、叔丁基羰基-4-甲基苯基磺酰基重氮甲烷、2-萘基磺酰基苯甲酰基重氮甲烷、4-甲基苯基磺酰基-2-萘甲酰基重氮甲烷、甲基磺酰基苯甲酰基重氮甲烷、叔丁氧基羰基-4-甲基苯基磺酰基重氮甲烷等双磺酰基重氮甲烷或磺酰基羰基重氮甲烷。
作为上述N-磺酰氧基酰亚胺型光致产酸剂,可以举出与琥珀酰亚胺、萘二甲酰亚胺、邻苯二甲酰亚胺、环己基二甲酰亚胺、5-降冰片烯-2,3-二甲酰亚胺、7-氧杂双环[2.2.1]-5-庚烯-2,3-二甲酰亚胺等酰亚胺的氮原子结合的氢原子被三氟甲磺酰氧基、九氟丁磺酰氧基、十七氟辛磺酰氧基、2,2,2-三氟乙磺酰氧基、五氟苯磺酰氧基、4-三氟甲基苯磺酰氧基、4-氟苯磺酰氧基、甲苯磺酰氧基、苯磺酰氧基、萘磺酰氧基、樟脑磺酰氧基、辛磺酰氧基、十二烷基苯磺酰氧基、丁磺酰氧基、甲磺酰氧基等磺酰氧基取代的化合物。
作为苯偶姻磺酸酯型光致产酸剂,可以举出苯偶姻甲苯磺酸酯、苯偶姻甲磺酸酯、苯偶姻丁磺酸酯等。
作为连苯三酚三磺酸酯型光致产酸剂,可列举出连苯三酚、间苯三酚、儿茶酚、间苯二酚或氢醌的羟基全部被三氟甲磺酰氧基、九氟丁磺酰氧基、十七氟辛磺酰氧基、2,2,2-三氟乙磺酰氧基、五氟苯磺酰氧基、4-三氟甲基苯磺酰氧基、4-氟苯磺酰氧基、甲苯磺酰氧基、苯磺酰氧基、萘磺酰氧基、樟脑磺酰氧基、辛磺酰氧基、十二烷基苯磺酰氧基、丁磺酰氧基、甲磺酰氧基等磺酰氧基取代的化合物。
作为硝基苄基磺酸酯型光致产酸剂,可以举出2,4-二硝基苄基磺酸酯、2-硝基苄基磺酸酯、2,6-二硝基苄基磺酸酯等硝基苯甲醇与三氟甲磺酸、九氟丁磺酸、十七氟辛磺酸、2,2,2-三氟乙磺酸、五氟苯磺酸、4-三氟甲基苯磺酸、4-氟苯磺酸、甲苯磺酸、苯磺酸、萘磺酸、樟脑磺酸、辛磺酸、十二烷基苯磺酸、丁磺酸、甲磺酸等磺酸的酯。再有,用三氟甲基取代硝基而成的化合物也同样地可以作为光致产酸剂使用。
作为砜型光致产酸剂,可以举出双(苯基磺酰基)甲烷、双(4-甲基苯基磺酰基)甲烷、双(2-萘基磺酰基)甲烷、2,2-双(苯基磺酰基)丙烷、2,2-双(4-甲基苯基磺酰基)丙烷、2,2-双(2-萘基磺酰基)丙烷、2-甲基-2-(对甲苯磺酰基)苯丙酮、2-(环己基羰基)-2-(对甲苯磺酰基)丙烷、2,4-二甲基-2-(对甲苯磺酰基)戊烷-3-酮等。
作为O-芳基磺酰肟化合物或O-烷基磺酰肟化合物(磺酸肟酯)型光致产酸剂,可以举出:乙二肟衍生物型、经由噻吩、环己二烯的共轭体系长的磺酸肟酯型、用三氟甲基这样的吸电子基团增加了化合物的稳定性的磺酸肟酯型、使用了苯基乙腈等取代乙腈衍生物的磺酸肟酯型、磺酸双肟酯型等。
作为乙二肟衍生物型光致产酸剂,可以举出双-O-(对甲苯磺酰基)-α-二甲基乙二肟、双-O-(对甲苯磺酰基)-α-二苯基乙二肟、双-O-(对甲苯磺酰基)-α-二环己基乙二肟、双-O-(对甲苯磺酰基)-2,3-戊二酮=二肟、双-O-(正丁烷磺酰基)-α-二甲基乙二肟、双-O-(正丁烷磺酰基)-α-二苯基乙二肟、双-O-(正丁烷磺酰基)-α-二环己基乙二肟、双-O-(甲烷磺酰基)-α-二甲基乙二肟、双-O-(三氟甲烷磺酰基)-α-二甲基乙二肟、双-O-(2,2,2-三氟乙烷磺酰基)-α-二甲基乙二肟、双-O-(10-樟脑磺酰基)-α-二甲基乙二肟、双-O-(苯磺酰基)-α-二甲基乙二肟、双-O-(4-氟苯磺酰基)-α-二甲基乙二肟、双-O-(4-三氟甲基苯磺酰基)-α-二甲基乙二肟、双-O-(二甲苯磺酰基)-α-二甲基乙二肟、双-O-(三氟甲烷磺酰基)-1,2-环己二酮二肟、双-O-(2,2,2-三氟乙烷磺酰基)-1,2-环己二酮二肟、双-O-(10-樟脑磺酰基)-1,2-环己二酮二肟、双-O-(苯磺酰基)-1,2-环己二酮二肟、双-O-(4-氟苯磺酰基)-1,2-环己二酮二肟、双-O-(4-(三氟甲基)苯磺酰基)-1,2-环己二酮二肟、双-O-(二甲苯磺酰基)-1,2-环己二酮二肟等。
作为介入了噻吩、环己二烯的共轭体系长的肟磺酸酯型光致产酸剂,可列举出(5-(对甲苯磺酰基)氧基亚氨基-5H-噻吩-2-亚基)苯基乙腈、(5-(10-樟脑磺酰基)氧基亚氨基-5H-噻吩-2-亚基)苯基乙腈、(5-正辛烷磺酰氧基亚氨基-5H-噻吩-2-亚基)苯基乙腈、(5-(对甲苯磺酰基)氧基亚氨基-5H-噻吩-2-亚基)(2-甲基苯基)乙腈、(5-(10-樟脑磺酰基)氧基亚氨基-5H-噻吩-2-亚基)(2-甲基苯基)乙腈、(5-正辛烷磺酰氧基亚氨基-5H-噻吩-2-亚基)(2-甲基苯基)乙腈、(5-(4-(对甲苯磺酰氧基)苯磺酰基)氧基亚氨基-5H-噻吩-2-亚基)苯基乙腈、(5-(2,5-双(对甲苯磺酰氧基)苯磺酰基)氧基亚氨基-5H-噻吩-2-亚基)苯基乙腈等。
作为用三氟甲基这样的吸电子基团增加了化合物的稳定性的肟磺酸酯型光致产酸剂,可列举出2,2,2-三氟-1-苯基乙酮=O-(甲基磺酰基)肟,2,2,2-三氟-1-苯基乙酮=O-(10-樟脑磺酰基)肟,2,2,2-三氟-1-苯基乙酮=O-(4-甲氧基苯磺酰基)肟,2,2,2-三氟-1-苯基乙酮=O-(1-萘基磺酰基)肟、2,2,2-三氟-1-苯基乙酮=O-(2-萘基磺酰基)肟、2,2,2-三氟-1-苯基乙酮=O-(2,4,6-三甲基苯基磺酰基)肟、2,2,2-三氟-1-(4-甲基苯基)乙酮=O-(10-樟脑磺酰基)肟、2,2,2-三氟-1-(4-甲基苯基)乙酮=O-(甲基磺酰基)肟、2,2,2-三氟-1-(2-甲基苯基)乙酮=O-(10-樟脑磺酰基)肟、2,2,2-三氟-1-(2,4-二甲基苯基)乙酮=O-(10-樟脑磺酰基)肟、2,2,2-三氟-1-(2,4-二甲基苯基)乙酮=O-(1-萘基磺酰基)肟、2,2,2-三氟-1-(2,4-二甲基苯基)乙酮=O-(2-萘基磺酰基)肟、2,2,2-三氟-1-(2,4,6-三甲基苯基)乙酮=O-(10-樟脑磺酰基)肟、2,2,2-三氟-1-(2,4,6-三甲基苯基)乙酮=O-(1-萘基磺酰基)肟、2,2,2-三氟-1-(2,4,6-三甲基苯基)乙酮=O-(2-萘基磺酰基)肟、2,2,2-三氟-1-(4-甲氧基苯基)乙酮=O-(甲基磺酰基)肟、2,2,2-三氟-1-(4-甲硫基苯基)乙酮=O-(甲基磺酰基)肟、2,2,2-三氟-1-(3,4-二甲氧基苯基)乙酮=O-(甲基磺酰基)肟、2,2,2-三氟-1-(4-甲氧基苯基)乙酮=O-(4-甲基苯基磺酰基)肟、2,2,2-三氟-1-(4-甲氧基苯基)乙酮=O-(4-甲氧基苯基磺酰基)肟、2,2,2-三氟-1-(4-甲氧基苯基)乙酮=O-(4-十二烷基苯基磺酰基)肟、2,2,2-三氟-1-(4-甲氧基苯基)乙酮=O-(辛基磺酰基)肟、2,2,2-三氟-1-(4-甲硫基苯基)乙酮=O-(4-甲氧基苯基磺酰基)肟、2,2,2-三氟-1-(4-甲硫基苯基)乙酮=O-(4-十二烷基苯基磺酰基)肟、2,2,2-三氟-1-(4-甲硫基苯基)乙酮=O-(辛基磺酰基)肟、2,2,2-三氟-1-(4-甲硫基苯基)乙酮=O-(2-萘基磺酰基)肟、2,2,2-三氟-1-(2-甲基苯基)乙酮=O-(甲基磺酰基)肟、2,2,2-三氟-1-(4-甲基苯基)乙酮=O-(苯基磺酰基)肟、2,2,2-三氟-1-(4-氯苯基)乙酮=O-(苯基磺酰基)肟、2,2,3,3,4,4,4-七氟-1-苯基丁酮=O-(10-樟脑磺酰基)肟、2,2,2-三氟-1-(1-萘基)乙酮=O-(甲基磺酰基)肟、2,2,2-三氟-1-(2-萘基)乙酮=O-(甲基磺酰基)肟、2,2,2-三氟-1-(4-苄基苯基)乙酮=O-(甲基磺酰基)肟、2,2,2-三氟-1-(4-(苯基-1,4-二氧杂-丁-1-基)苯基)乙酮=O-(甲基磺酰基)肟、2,2,2-三氟-1-(1-萘基)乙酮=O-(丙基磺酰基)肟、2,2,2-三氟-1-(2-萘基)乙酮=O-(丙基磺酰基)肟、2,2,2-三氟-1-(4-苄基苯基)乙酮=O-(丙基磺酰基)肟、2,2,2-三氟-1-(4-甲基磺酰基苯基)乙酮=O-(丙基磺酰基)肟、2,2,2-三氟-1-(4-甲基磺酰氧基苯基)乙酮=O-(丙基磺酰基)肟、2,2,2-三氟-1-(4-甲基羰氧基苯基)乙酮=O-(丙基磺酰基)肟、2,2,2-三氟-1-(6H,7H-5,8-二氧代萘甲酰-2-基)乙酮=O-(丙基磺酰基)肟、2,2,2-三氟-1-(4-甲氧基羰基甲氧基苯基)乙酮=O-(丙基磺酰基)肟、2,2,2-三氟-1-(4-(甲氧基羰基)-(4-氨基-1-氧杂-戊-1-基)苯基)乙酮=O-(丙基磺酰基)肟、2,2,2-三氟-1-(3,5-二甲基-4-乙氧基苯基)乙酮=O-(丙基磺酰基)肟、2,2,2-三氟-1-(4-苄氧基苯基)乙酮=O-(丙基磺酰基)肟、2,2,2-三氟-1-(2-噻吩基)乙酮=O-(丙基磺酸酯)肟、和2,2,2-三氟-1-(1-二氧杂噻吩-2-基)乙酮=O-(丙基磺酸酯)肟、2,2,2-三氟-1-(4-(3-(4-(2,2,2-三氟-1-(三氟甲磺酰氧基亚氨基)乙基)苯氧基)丙氧基)苯基)乙酮=O-(三氟甲磺酰基)肟、2,2,2-三氟-1-(4-(3-(4-(2,2,2-三氟-1-(1-丙磺酰氧基亚氨基)乙基)苯氧基)丙氧基)苯基)乙酮=O-(丙基磺酰基)肟、2,2,2-三氟-1-(4-(3-(4-(2,2,2-三氟-1-(1-丁磺酰氧基亚氨基)乙基)苯氧基)丙氧基)苯基)乙酮=O-(丁基磺酰基)肟、2,2,2-三氟-1-(4-(3-(4-(2,2,2-三氟-1-(4-(4-甲基苯基磺酰氧基)苯基磺酰氧基亚氨基)乙基)苯氧基)丙氧基)苯基)乙酮=O-(4-(4-甲基苯基磺酰氧基)苯基磺酰基)肟、2,2,2-三氟-1-(4-(3-(4-(2,2,2-三氟-1-((2,5-双(4-甲基苯基磺酰氧基)苯磺酰氧基)苯基磺酰氧基亚氨基)乙基)苯氧基)丙氧基)苯基)乙酮=O-((2,5-双(4-甲基苯基磺酰氧基)苯磺酰氧基)苯基磺酰基)肟等。
作为使用了取代乙腈衍生物的肟磺酸酯型光致产酸剂,可列举出α-(对甲苯磺酰氧基亚氨基)-苯基乙腈、α-(对氯苯磺酰氧基亚氨基)-苯基乙腈、α-(4-硝基苯磺酰氧基亚氨基)-苯基乙腈、α-(4-硝基-2-三氟甲基苯磺酰氧基亚氨基)-苯基乙腈、α-(苯磺酰氧基亚氨基)-4-氯苯基乙腈、α-(苯磺酰氧基亚氨基)-2,4-二氯苯基乙腈、α-(苯磺酰氧基亚氨基)-2,6-二氯苯基乙腈、α-(苯磺酰氧基亚氨基)-4-甲氧基苯基乙腈、α-(2-氯苯磺酰氧基亚氨基)-4-甲氧基苯基乙腈、α-(苯磺酰氧基亚氨基)-2-噻吩基乙腈、α-(4-十二烷基苯磺酰氧基亚氨基)-苯基乙腈、α-((4-甲苯磺酰氧基亚氨基)-4-甲氧基苯基)乙腈、α-((十二烷基苯磺酰氧基亚氨基)-4-甲氧基苯基)乙腈、α-(甲苯磺酰氧基亚氨基)-3-噻吩基乙腈、α-(甲基磺酰氧基亚氨基)-1-环戊烯基乙腈、α-(乙基磺酰氧基亚氨基)-1-环戊烯基乙腈、α-(异丙基磺酰氧基亚氨基)-1-环戊烯基乙腈、α-(正丁基磺酰氧基亚氨基)-1-环戊烯基乙腈、α-(乙基磺酰氧基亚氨基)-1-环己烯基乙腈、α-(异丙基磺酰氧基亚氨基)-1-环己烯基乙腈、α-(正丁基磺酰氧基亚氨基)-1-环己烯基乙腈等。
另外,作为双肟磺酸酯型光致产酸剂,可以举出双(α-(对甲苯磺酰氧基)亚氨基)-对-亚苯基二乙腈、双(α-(苯磺酰氧基)亚氨基)-对-亚苯基二乙腈、双(α-(甲磺酰氧基)亚氨基)-对-亚苯基二乙腈、双(α-(丁磺酰氧基)亚氨基)-对-亚苯基二乙腈、双(α-(10-樟脑磺酰氧基)亚氨基)-对-亚苯基二乙腈、双(α-(三氟甲磺酰氧基)亚氨基)-对-亚苯基二乙腈、双(α-(4-甲氧基苯磺酰氧基)亚氨基)-对-亚苯基二乙腈、双(α-(对甲苯磺酰氧基)亚氨基)-间-亚苯基二乙腈、双(α-(苯磺酰氧基)亚氨基)-间-亚苯基二乙腈、双(α-(甲磺酰氧基)亚氨基)-间-亚苯基二乙腈、双(α-(丁磺酰氧基)亚氨基)-间-亚苯基二乙腈、双(α-(10-樟脑磺酰氧基)亚氨基)-间-亚苯基二乙腈、双(α-(三氟甲磺酰氧基)亚氨基)-间-亚苯基二乙腈、双(α-(4-甲氧基苯磺酰氧基)亚氨基)-间-亚苯基二乙腈等。
另外,下述式(C1)所示的肟磺酸酯也可以作为光致产酸剂使用。
[化1]
式(C1)中,R1是取代或未取代的碳原子数为1~10的卤代烷基磺酰基或卤代苯磺酰基。R2是碳原子数为1~11的卤代烷基。R3是取代或未取代的芳基或杂芳基。
作为由式(C1)表示的肟磺酸酯,可以举出2-(2,2,3,3,4,4,5,5-八氟-1-(九氟丁基磺酰氧基亚氨基)戊基)芴、2-(2,2,3,3,4,4-五氟-1-(九氟丁基磺酰氧基亚氨基)丁基)芴、2-(2,2,3,3,4,4,5,5,6,6-十氟-1-(九氟丁基磺酰氧基亚氨基)己基)芴、2-(2,2,3,3,4,4,5,5-八氟-1-(九氟丁基磺酰氧基亚氨基)戊基)-4-联苯、2-(2,2,3,3,4,4-五氟-1-(九氟丁基磺酰氧基亚氨基)丁基)-4-联苯、2-(2,2,3,3,4,4,5,5,6,6-十氟-1-(九氟丁基磺酰氧基亚氨基)己基)-4-联苯等。
作为其中优选使用的光致产酸剂,为锍盐、双磺酰基重氮甲烷、N-磺酰氧基酰亚胺、磺酰肟化合物类。
根据聚合物中使用的酸不稳定基团的易断性等,最佳的产生酸的阴离子不同,但一般选择没有挥发性的阴离子、扩散性不极度高的阴离子。在这种情况下,优选的阴离子为苯磺酸阴离子、甲苯磺酸阴离子、4-(4-甲苯磺酰氧基)苯磺酸阴离子、五氟苯磺酸阴离子、2,2,2-三氟乙磺酸阴离子、九氟丁磺酸阴离子、十七氟辛磺酸阴离子、樟脑磺酸阴离子。
就(C)光致产酸剂的含量而言,相对于(A)成分的树脂100质量份,优选为0.2~20质量份,更优选为0.3~10质量份。如果含量在上述范围内,则可以得到实用上没有问题的感光度和图案形状。(C)成分的光致产酸剂可以单独使用1种,也可以将2种以上组合使用。另外,也可以使用曝光波长处的透射率低的光致产酸剂,通过其添加量来控制抗蚀剂膜中的光透射率。
[(D)在1分子中含有平均4个以上的环氧基的环氧化合物]
(D)成分是在1分子中含有平均4个以上的环氧基的环氧化合物,作为交联剂发挥功能。作为这样的化合物,可以举出下述式(D1)~(D3)中的任一个所示的化合物,但并不限定于这些。
[化2]
在式(D1)中,m是0~2的整数。n是2以上的整数,优选2~10的整数。
在式(D1)中,R11是碳原子数1~6的饱和烃基。所述饱和烃基可以是饱和的,也可以是不饱和的,可以是直链状、支链状、环状的任一种。作为其具体例,可以举出甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、正己基等碳原子数1~3的烷基;环丙基、环丁基、环戊基、环己基等碳原子数3~6的环式饱和烃基。
在式(D1)中,L1各自独立地为碳原子数1~10的饱和亚烃基。所述亚烃基可以是直链状、支链状、环状中的任一种,作为其具体例,可以举出亚甲基、亚乙基、丙烷-1,2-二基、丙烷-1,3-二基、丙烷-2,2-二基、丁烷-1,2-二基、丁烷-1,3-二基、丁烷-1,4-二基等亚烷基;亚环丙基、环戊烷-1,2-二基、环己烷-1,2-二基等环式饱和亚烃基。其中,优选亚甲基、亚乙基、丙烷-1,2-二基、丙烷-1,3-二基、丙烷-2,2-二基等。
在式(D2)和(D3)中,p是4~8的整数。q是2~4的整数。R12是碳原子数6~30的p价的烃基,可以含有选自氮原子、氧原子和硫原子中的至少一种。R13是碳原子数6~20的q价的烃基,可以含有选自氮原子、氧原子和硫原子中的至少一种。
作为式(D2)所示的化合物,可以举出以下所示的化合物,但不限于此。
[化3]
作为式(D3)所示的化合物,可以举出以下所示的化合物,但不限于此。
[化4]
作为式(D1)~(D3)中的任一个所示的化合物,特别优选含有芳环的化合物。
就(D)成分的含量而言,相对于(A)成分100质量份,优选为10~200质量份,更优选为30~100质量份。(D)成分的环氧化合物可以单独使用1种,也可以将2种以上组合使用。
[(E)苯并三唑化合物、咪唑化合物]
作为(E)成分的苯并三唑化合物,可列举出由下述式(E1)或(E2)表示的化合物。
[化5]
式(E1)和(E2)中,R21和R23各自独立地为氢原子、羟基、氨基、可具有取代基的碳原子数1~6的烷基、可具有取代基的苯基、具有磺酰基的取代基、或-A1-A2。A1是羰基、碳原子数1~12的饱和亚烃基或-A11-O-,A11是碳原子数1~12的饱和亚烃基。A2是氢原子、卤素原子、氰基、羟基、碳原子数1~6的饱和烃氧基、羧基或各烃基的碳原子数为1~6的二烃基氨基。上述饱和亚烃基和饱和烃氧基和二烃基氨基的烃基部可以是直链状、支链状、环状的任一种。
式(E1)和(E2)中,R22和R24各自独立地为氢原子、卤素原子、羟基、可具有取代基的碳原子数1~6的饱和烃基、碳原子数1~6的饱和烃氧基、具有磺酰基的取代基或由下述式(E3)表示的有机基团。
[化6]
(式中,R25是氢原子或可被取代的碳原子数1~12的饱和烃基。a是0或1。虚线是键合端。)
作为上述苯并三唑化合物,优选苯并三唑、1-羟基苯并三唑、1-甲基苯并三唑、1-羟基甲基苯并三唑、1-乙基苯并三唑、1-(1-羟基乙基)苯并三唑、1-(2-羟基乙基)苯并三唑、1-丙基苯并三唑、1-(1-羟基丙基)苯并三唑、1-(2-羟基丙基)苯并三唑、1-(3-羟基丙基)苯并三唑、4-羟基-1H-苯并三唑、5-甲基-1H-苯并三唑、苯并三唑-5-羧酸、1-甲基苯并三唑-5-羧酸、1-乙基苯并三唑-5-羧酸、1-叔丁基苯并三唑-5-羧酸、1-(2-环戊基乙基)苯并三唑-5-羧酸、1H-苯并三唑-4-磺酸、1H-苯并三唑-1-乙腈、1H-苯并三唑-1-甲醛、2-甲基-2H-苯并三唑、2-乙基-2H-苯并三唑等。
接着,作为(E)成分的咪唑化合物,可以举出由下述式(E4)~(E9)表示的化合物。
[化7]
式(E4)~(E9)中,R31是氢原子、或具有选自羟基、羰基、酯基、醚基、硫醚基、碳酸酯基、氰基及缩醛基中的至少一个极性官能团的碳原子数2~20的饱和烃基。R32、R33和R34各自独立地为氢原子、碳原子数1~10的饱和烃基、碳原子数6~10的芳基或碳原子数7~10的芳烷基。R35、R37、R39和R43各自独立地为碳原子数1~10的饱和亚烃基。R36和R38各自独立地为氢原子或碳原子数1~15的饱和烃基,所述饱和烃基可包含选自羟基、羰基、酯基、醚基、硫醚基、碳酸酯基、氰基和缩醛基中的至少一种。R40是碳原子数1~15的饱和烃基,可含有选自羟基、羰基、酯基、醚基、硫醚基、碳酸酯基、氰基和缩醛基中的至少一种。R41是(b+1)价的碳原子数2~10的烃基。R42各自独立地为氢原子或碳原子数1~15的饱和烃基,所述饱和烃基可含有选自羟基、羰基、酯基、醚基、硫醚基、碳酸酯基、氰基及缩醛基中的至少一种,另外,两个R42可以结合以形成环。b是2、3、4或5。
作为上述咪唑化合物,优选咪唑、2-甲基咪唑、1,2-二甲基咪唑、2-乙基-4-甲基咪唑、2-苯基咪唑、2-苯基-4-甲基咪唑、1-甲氧基甲基咪唑、N-叔丁氧基羰基咪唑、1-(2-氰基乙基)-2-甲基咪唑、1-(2-羟基乙基)咪唑、1-(羧基甲基)咪唑、2-甲基-1-乙烯基咪唑等。
就(E)成分的含量而言,相对于(A)成分100质量份,优选为0.01~10质量份,更优选为0.02~5质量份。如果(E)成分的含量在上述范围内,则可以以实用的感光度形成图案。(E)成分的化合物可以单独使用1种,也可以将2种以上组合使用。
[(F)表面活性剂]
上述负型抗蚀剂膜还可以包含(F)表面活性剂。作为(F)表面活性剂,可以举出聚氧乙烯月桂基醚、聚氧乙烯硬脂基醚、聚氧乙烯十六烷基醚、聚氧乙烯油基醚等聚氧乙烯烷基醚类、聚氧乙烯辛基苯基醚、聚氧乙烯壬基苯基醚等聚氧乙烯烷基烯丙基醚类、聚氧乙烯聚氧丙烯嵌段共聚物类、山梨糖醇酐单月桂酸酯、山梨糖醇酐单棕榈酸酯、山梨糖醇酐单硬脂酸酯等山梨糖醇酐脂肪酸酯类、聚氧乙烯山梨糖醇酐单月桂酸酯、聚氧乙烯山梨糖醇酐单棕榈酸酯、聚氧乙烯山梨糖醇酐单硬脂酸酯、聚醚有机硅、聚氧乙烯山梨糖醇酐三油酸酯、聚氧乙烯山梨糖醇酐三硬脂酸酯等聚氧乙烯山梨糖醇酐脂肪酸酯的非离子系表面活性剂;EFTOP(注册商标)EF301、EF303、EF352((株)Tohkem Products制)、MEGAFAC(注册商标)F171、F172、F173(DIC(株)制)、FLUORAD(注册商标)FC-4430、FC-430、FC-431(3M公司制)、Surflon(注册商标)E1004(日信化学工业(株)制)、Asahi Guard(注册商标)AG710(旭硝子(株)制)、Surflon(注册商标)S-381、S-382、SC101、SC102、SC103、SC104、SC105、SC106、KH-10、KH-20、KH-30、KH-40(AGC Semichemical(株)制)等氟系表面活性剂;有机硅氧烷聚合物KP-341、X-70-092、X-70-093(信越化学工业(株)制);丙烯酸系或甲基丙烯酸系PolyflowNo.75、No.95(共荣社化学(株)制)等。其中,优选FLUORAD FC-4430、KP-341、X-70-093。它们可以单独使用1种或组合使用2种以上。
就(F)成分的表面活性剂的含量而言,相对于(A)成分的树脂100质量份,为0~5质量份,在含有的情况下优选为0.01~2质量份。(F)成分的表面活性剂可以单独使用1种,也可以将2种以上组合使用。
[其他成分]
另外,在不妨碍本发明的效果的范围内,可以在上述负型抗蚀剂膜中进一步添加其他公知的添加剂。作为上述添加剂,例如可以举出各种光致产碱剂、增感剂、水溶性纤维素等溶解促进剂、聚乙烯醇、聚乙烯基烷基醚化合物等应力缓和剂、偶氮化合物、姜黄素等染料、草酸等形状改善剂等。只要不损害本发明的效果,所述添加剂的含量是任意的。
[负型抗蚀剂膜层叠体的制造方法]
对本发明的负型抗蚀剂膜层叠体的制造方法进行说明。首先,将上述的(A)成分、(B)成分、(C)成分、(D)成分和(E)成分以及根据需要的(F)成分、其他成分同时或以任意顺序溶解于有机溶剂中,制备均匀的负型抗蚀剂溶液。根据需要,也可以对得到的均匀的溶液使用过滤器进行过滤。
上述有机溶剂只要对其他成分具有充分的溶解性、具有良好的涂膜性,则没有特别限定。作为这样的有机溶剂,可以举出甲基溶纤剂、乙基溶纤剂、甲基溶纤剂乙酸酯、乙基溶纤剂乙酸酯等溶纤剂系溶剂;丙二醇、二丙二醇等丙二醇系溶剂;丙二醇单甲醚、丙二醇单丁醚等丙二醇烷基醚系溶剂;丙二醇单甲醚乙酸酯、丙二醇二甲醚、丙二醇单乙醚乙酸酯等丙二醇烷基醚乙酸酯系溶剂;乙酸丁酯、乙酸戊酯、乳酸甲酯、乳酸乙酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯等酯系溶剂;甲醇、乙醇、异丙醇、丁醇、己醇、二丙酮醇等醇系溶剂;丙酮、环己酮、环戊酮、甲乙酮、甲基戊基酮、甲基异丁基酮等酮系溶剂;甲基苯基醚、二甘醇二甲醚等醚系溶剂;N,N-二甲基甲酰胺、N-甲基吡咯烷酮、二甲基亚砜等高极性溶剂;以及它们的混合溶剂。
作为特别优选的有机溶剂,可列举出丙二醇烷基醚乙酸酯系溶剂、乳酸烷基酯、烷基酮。作为上述丙二醇烷基醚乙酸酯的烷基,可以举出碳原子数1~4的烷基,例如甲基、乙基、丙基等,优选为甲基和乙基。另外,丙二醇烷基醚乙酸酯中有1,2取代物和1,3取代物,并且根据取代位置的组合有3种异构体,它们也可以是混合物。另外,乳酸烷基酯的烷基可以举出碳原子数1~4的烷基,例如甲基、乙基、丙基等,优选甲基和乙基。作为烷基酮的烷基,可以举出碳原子数1~10的烷基,例如甲基、乙基、丙基、异丁基、环戊基、环己基等,特别优选异丁基、环戊基、环己基。
在制备上述负型抗蚀剂溶液时,相对于(A)成分的树脂100质量份,上述有机溶剂的使用量优选为20~1000质量份,更优选为30~200质量份。如果有机溶剂的使用量在上述范围内,则能够以均匀的膜厚制造膜,在膜中不会产生缺陷。在本发明中,一旦在过剩的有机溶剂中均匀地溶解构成成分,经过后述的干燥工序,制作目标的负型抗蚀剂膜层叠体,因此在构成成分的溶解时,使用的有机溶剂的量可以根据制作的膜的膜厚适当调整。
将上述负型抗蚀剂溶液在清洁度1000以下的洁净室中,使用设置在管理为温度5~45℃、优选15~35℃、且湿度5~90%、优选10~70%的区域的正向辊涂机、反向辊涂机、缺角轮涂布机、模压涂布机、唇式涂布机、凹版涂布机、浸涂机、气刀涂布机、毛细管涂布机、R&R(raising and rising)涂布机、刮刀涂布机、棒涂机、涂布器、挤出成型机等,涂布在作为第一支承体的热塑性膜(脱模基材)上。此时,涂布速度优选为0.05~1000m/分钟,更优选为0.1~500m/分钟。然后,将涂布了负型抗蚀剂溶液的热塑性膜在在线干燥器(热风循环烘箱)中,优选在40~130℃、1~40分钟、更优选在50~120℃、2~30分钟下除去有机溶剂和挥发成分,使其干燥,形成负型抗蚀剂膜层叠体。再有,也可以代替在线干燥器而使用基于红外线照射等的溶剂除去、同时使用在线干燥器和红外线照射的方法等多个干燥方法进行溶剂除去而形成负型抗蚀剂膜层叠体。另外,根据需要,也可以使用辊式层压机将保护膜(脱模基材)压接在上述负型抗蚀剂膜层叠体上,进行层叠。
再有,在本发明中,通过在热塑性膜使用特定的成型条件及成型机将负型抗蚀剂溶液交付生产线,从而能够可连续地被辊膜化、处理成所希望的形状的辊膜,另外,在负型抗蚀剂膜层叠体上形成保护膜的情况下也同样。
例如,在将支承膜从膜涂布机的卷出轴卷出并通过膜涂布机头时,在支承膜上以规定的厚度涂布负型抗蚀剂溶液,以规定的温度和规定的时间通过热风循环烘箱,在上述支承膜上干燥后,与从膜涂布机的另外的卷出轴卷出的保护膜一起以规定的压力通过层压辊,与支承膜上的上述负型抗蚀剂层贴合后,卷绕于膜涂布机的卷绕轴,采用该方法能够以卷形态制造负型抗蚀剂膜层叠体。
作为上述保护膜,与热塑性膜同样地,只要不损害负型抗蚀剂膜的形态,能够从负型抗蚀剂膜剥离,则没有特别限定,可以使用单一膜或层叠了多个聚合物膜的多层膜。具体而言,可以举出尼龙膜、聚乙烯(PE)膜、聚对苯二甲酸乙二醇酯(PET)膜、聚萘二甲酸乙二醇酯膜、聚苯硫醚(PPS)膜、聚丙烯(PP)膜、聚苯乙烯膜、聚甲基戊烯(TPX)膜、聚碳酸酯膜、含氟膜、特殊聚乙烯醇(PVA)膜、实施了脱模处理的聚酯膜等塑料膜。
其中,作为保护膜,优选具有适度的可挠性的PET膜、PE膜。它们可以使用市售品,作为PET膜,可以列举出Cerapeel(注册商标)WZ(RX)、BX8(R)(东丽膜加工(株)制)、E7302、E7304(东洋纺(株)制)、PET38×1-A3、PET38×1-V8、PET38×1-X08(Nippa(株)制)等,作为PE膜,例如可以举出GF-8(Tamapoly(株)制)、PE膜0型(Nippa(株)制)、Toretec(注册商标)7332、7111、7721(东丽膜加工(株)制)等。
就上述热塑性膜及保护膜的厚度而言,从制造的稳定性及防止对于卷芯的容易打卷所谓卷曲的观点出发,均优选为10~150μm,更优选25~100μm。
这样制造的卷状的负型抗蚀剂膜层叠体由于保存稳定性优异,所以可以长期使用。
上述负型抗蚀剂膜在上述热塑性膜上形成以能够转印到第二支承体上。上述负型抗蚀剂膜的厚度优选为5~250μm,更优选为10~180μm。再有,作为第二支承体,可以举出塑料膜或片、Si、Cu、SiO2、SiN、SiON、TiN、WSi、BPSG、SOG等半导体基板、Au、Ti、W、Cu、Ni-Fe、Ta、Zn、Co、Pb等金属基板、有机减反射膜等基板、有机基板等。在第二支承体表面,也可以形成采用镀敷、溅射等形成的电路、绝缘性树脂的形成等引起的台阶高差(凹凸)。所述台阶高差优选为0~200μm左右的范围,更优选为3~100μm左右的范围,进一步优选为10~50μm左右的范围。
保护膜对于在上述工序中制造的负型抗蚀剂膜的剥离力通常为0.1~500gf/24mm的范围,以下记述其测定方法。试验方法按照JIS Z0237中记载的“将剥离衬里相对于压敏胶带粘合面剥离的粘合力试验方法”进行。试验环境为标准状态(温度为23±1℃,相对湿度为50±5%)。试验中使用的膜宽为24mm,如果膜宽变动,则剥离力变化,因此不优选。制作规定尺寸的膜后,使用试验机测定时,保护膜的剥离角度为180°,剥离速度为5.0±0.2mm/秒。应予说明,作为测定值,将最初的25mm的测定值除外,将接下来的50mm的平均值用作试验值。
[图案形成方法]
使用真空层压机、辊层压机等各种层压机,将本发明的负型抗蚀剂膜层叠体的抗蚀剂膜粘贴在第二支承体,特别是半导体基板上,剥离热塑性膜,由此能够转印负型抗蚀剂膜。第二支承体可以具有台阶高差结构,通过根据台阶高差的高度来使用适当的负型抗蚀剂膜厚,从而可以在台阶高差内埋入负型抗蚀剂膜,对于具有0~200μm左右的台阶高差的支承体,能够优选使用。转印后,即使不特别进行加热也没有问题,但从提高与基板的密合性的观点出发优选进行加热处理,在进行加热处理的情况下,可以在热板上或烘箱中在60~150℃下预烘焙1~30分钟,优选在80~130℃下预烘焙1~10分钟。
接着,用选自紫外线、远紫外线、EB等中的放射线、优选波长300nm以上、更优选波长350~500nm的放射线,通过规定的掩模进行曝光。曝光量优选为10~5000mJ/cm2左右,更优选为30~2000mJ/cm2左右。曝光后,根据需要,从提高感光度的观点出发,在热板上进行优选60~150℃、1~10分钟、更优选80~120℃、1~5分钟的曝光后烘焙(PEB)。
然后,使用0.1~5质量%、优选2~3质量%的TMAH等碱水溶液的显影液,优选以0.1~60分钟、更优选以0.5~15分钟,采用浸渍(dip)法、旋覆浸没(puddle)法、喷雾(spray)法等公知的方法显影,从而在第二支承体上形成目标图案。图案形成后,也可以根据需要对表面进行冲洗处理。
进而,在显影工序后,可以通过电镀或化学镀敷形成金属镀层,形成镀敷图案。作为电镀或化学镀敷,可以举出电镀Cu、化学镀Cu、电镀Ni、化学镀Ni、电镀Au等,可以在公知的镀浴、镀敷条件下进行镀敷。再有,镀层的厚度一般以抗蚀剂图案的厚度的80~100%形成。例如,种子层为Cu,在其上形成厚度为1μm抗蚀剂图案后,通过电镀Cu,形成厚度0.8~1μm的镀Cu图案。
实施例
以下,示出合成例、实施例及比较例来具体说明本发明,但本发明不限于下述实施例。
[1]酚醛清漆树脂的合成
[合成例1]
在装有搅拌器、冷凝器及温度计的3口烧瓶中,装入对甲酚54.1g(0.5mol)、间甲酚43.3g(0.4mol)、2,5-二甲基苯酚12.2g(0.1mol)37质量%甲醛水溶液52.3g(0.549mol)和作为缩聚催化剂的草酸二水合物0.30g(2.40×10-3mol),将烧瓶浸入油浴中,将烧瓶内的温度保持在100℃,进行80分钟的缩聚。反应结束后,加入500mL的甲基异丁基酮(MIBK),搅拌30分钟后,分离水层,将提取到MIBK层的产物用300mL的纯水水洗5次后,分液,用蒸发器以4mmHg进行150℃的减压汽提,得到了重均分子量(Mw)6000的酚醛清漆树脂(87g)。再有,Mw的测定使用东曹(株)制、GPC柱(G-2000H6:2根,G-3000H6:1根,G-4000H6:1根),在流量1.5mL/分钟、洗脱溶剂THF、柱温度40℃下进行。
[2]负型抗蚀剂膜层叠体的制作
[实施例1~8、比较例1~4]
按照下述表1所示的组成,将(A)~(F)成分及其他成分混合以制备溶液后,用1.0μm的膜滤器过滤,制备抗蚀剂溶液1~12。
应予说明,表1中的各成分如下所述。
(A)具有酚羟基的碱可溶性树脂
·NP1:合成例1中合成的酚醛清漆树脂
·EP6050G:旭有机材(株)制酚醛清漆树脂(Mw=2500-4000)
(B)聚酯
·PE1:PolysizerW-2050(DIC(株)制己二酸系聚酯,Mw=3900)
·PE2:ADK Cizer P-300((株)ADEKA制己二酸系聚酯,Mw=4900)
(C)光致产酸剂
·PAG1:PAI-101(Midori Kagaku Co.,Ltd.制)
·PAG2:HT-1CS(San-Apro Ltd制)
(D)交联剂
·CL1:EOCN-1020(日本化药(株)制)、环氧当量191-207
[化8]
·CL2:TEPIC-UC(日产化学(株)制)、环氧当量185-205
[化9]
·CL3:TEP-G(旭有机材(株)制)、环氧当量160-180
[化10]
·CL4:Nikalak MW-30HM((株)三和化学制甲基化三聚氰胺)
(E)苯并三唑化合物、咪唑化合物
·BTA-1:苯并三唑
·4MI:4-甲基咪唑
(F)有机溶剂
·CP:环戊酮
·PGMEA:丙二醇单甲醚乙酸酯
(其他成分)
·KP-341:信越化学工业(株)制
·NT-300P:东洋合成工业(株)制
·姜黄素:(株)三和化学制
·TrisP-PA:本州化学工业(株)制
[表1]
将抗蚀剂溶液1~12在清洁度为1000、湿度为40~45%、温度为22~26℃的洁净室中,使用模压涂布机作为膜涂布机,在作为热塑性膜的PET膜(厚度38μm)上涂布,用热风循环烘箱在表2记载的烘箱温度下干燥5分钟,制作具有膜厚40μm的负型抗蚀剂膜的层叠体。然后,在制作的抗蚀剂膜的表面,将作为保护膜的PE膜(厚度50μm)以1MPa的压力贴合,以卷状态制作了负型抗蚀剂膜层叠体1~12。
[表2]
[3]对产生空隙的评价
对于制作的负型抗蚀剂膜层叠体1~12,首先,剥离保护膜,使用真空层压机TEAM-100M((株)TAKATORI制),将真空腔室内设定为真空度80Pa,将热塑性膜上的负型抗蚀剂膜转印到最大具有50μm的台阶高差的200mm的Cu基板上。此时的温度条件为60℃。返回常压后,从真空层压机取出上述基板,剥离热塑性膜后,使用光学显微镜((株)尼康制)评价基板上是否产生空隙。对各实施例及比较例进行5次评价,用其平均值进行判定。没有产生空隙的记为○。将结果示于表3。
[表3]
负型抗蚀剂膜层叠体 | 产生空隙 | |
实施例1 | 1 | ○ |
实施例2 | 2 | ○ |
实施例3 | 3 | ○ |
实施例4 | 4 | ○ |
实施例5 | 5 | ○ |
实施例6 | 6 | ○ |
实施例7 | 7 | ○ |
实施例8 | 8 | ○ |
比较例1 | 9 | ○ |
比较例2 | 10 | 层叠时产生裂纹 |
比较例3 | 11 | 层叠时产生裂纹 |
比较例4 | 12 | ○ |
[4]保存稳定性评价
将制作的卷状态的负型抗蚀剂膜层叠体1~12在23℃下保存,确认了1个月后的膜状态。将结果示于表4。
[表4]
负型抗蚀剂膜层叠体 | 保存稳定性 | |
实施例1 | 1 | 无变化 |
实施例2 | 2 | 无变化 |
实施例3 | 3 | 无变化 |
实施例4 | 4 | 无变化 |
实施例5 | 5 | 无变化 |
实施例6 | 6 | 无变化 |
实施例7 | 7 | 无变化 |
实施例8 | 8 | 无变化 |
比较例1 | 9 | 无变化 |
比较例2 | 10 | 使用时产生裂纹 |
比较例3 | 11 | 使用时产生裂纹 |
比较例4 | 12 | 无变化 |
[5]图案形成的评价
使用真空层压机将负型抗蚀剂膜层叠体1~12层压在分别通过溅射蒸镀了Cu的8英寸硅晶片上,接着在热板上在110℃下进行5分钟预烘焙。接着,将形成的感光性树脂被膜经由中间掩模使用i线用步进式曝光机((株)尼康制NSR-2205i11D)曝光,在100℃下进行了2分钟PEB后,使用2.38质量%TMAH水溶液即碱显影液进行5分钟喷雾显影,干燥,形成了图案。
对于得到的图案,使用扫描型电子显微镜((株)日立高新技术制S-4700),进行最佳曝光量及分辨率的确认。应予说明,最佳曝光量设为50μm尺寸的孔图案成为50μm的曝光量,分辨率设为以最佳曝光量对最小的孔图案进行析像的掩模尺寸。将结果示于表5。
[表5]
[6]耐溶剂性评价
使用真空层压机将负型抗蚀剂膜层叠体1~12层压在8英寸硅晶片上,接着在热板上进行110℃、5分钟的预烘焙后,使用烘箱在190℃下进行了2小时的热处理。然后,将晶片在50℃下在下述表6所示的各种溶剂中浸渍15分钟,将未溶解的情形记为○,将观察到部分溶解的情形记为△,将完全溶解的情形记为×。
[表6]
Claims (5)
1.负型抗蚀剂膜层叠体,其具备作为第一支承体的热塑性膜、和负型抗蚀剂膜,所述负型抗蚀剂膜包含:
(A)具有酚羟基的碱可溶性树脂,
(B)包含聚酯的增塑剂,
(C)光致产酸剂,
(D)在1分子中含有平均4个以上的环氧基的环氧化合物,以及
(E)苯并三唑化合物和/或咪唑化合物。
2.根据权利要求1所述的层叠体,其中,所述聚酯是具有2~6个羧基的多元羧酸系聚酯。
3.图案形成方法,其包括:
(1)在第二支承体上转印根据权利要求1或2所述的层叠体的负型抗蚀剂膜的工序,
(2)对所述抗蚀剂膜进行曝光的工序,和
(3)利用碱水溶液对所述抗蚀剂膜进行显影的工序。
4.根据权利要求3所述的图案形成方法,其中,在工序(1)中,转印后进行加热处理。
5.根据权利要求3或4所述的图案形成方法,其中,在工序(2)中,曝光后进行加热处理。
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