CN108264605A - 单体、聚合物和光致抗蚀剂组合物 - Google Patents
单体、聚合物和光致抗蚀剂组合物 Download PDFInfo
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- CN108264605A CN108264605A CN201711424429.3A CN201711424429A CN108264605A CN 108264605 A CN108264605 A CN 108264605A CN 201711424429 A CN201711424429 A CN 201711424429A CN 108264605 A CN108264605 A CN 108264605A
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- RIXVESSVKLKKFV-UHFFFAOYSA-N piperazine-1,4-dicarboxylic acid Chemical class OC(=O)N1CCN(C(O)=O)CC1 RIXVESSVKLKKFV-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- 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
- C07C323/11—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 having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/13—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 having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated and containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- 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
- C07C323/17—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 having the sulfur atom of at least one of the thio groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—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 carboxyl groups bound to the same carbon skeleton
- C07C323/61—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 carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/24—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
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Abstract
提供包含碳脂环基或杂脂环基的单体和聚合物,所述基团包含1)一个或多个酸不稳定环取代基和2)一个或多个醚或硫醚环取代基。还提供包含这类聚合物的光致抗蚀剂。
Description
背景技术
本发明大体上涉及电子装置的制造。更具体来说,本发明涉及光致抗蚀剂组合物和光刻方法,其允许使用负性显影方法形成精细图案。
光致抗蚀剂是用于将图像转移到衬底的感光膜。在衬底上形成光致抗蚀剂涂层并且随后通过光掩模使光致抗蚀剂层曝光于活化辐射源。在暴露后,使光致抗蚀剂显影以提供准许选择性加工衬底的浮雕图像。
已经付出了很大的努力来扩展光致抗蚀剂组合物的实际分辨率能力,包括通过研发各种抗蚀剂组合物材料。参见JP2015111637A;US20160077429;WO2011111807A1;JP2012031381A;US20130004740A1;US8841060B2;JP5618924B2;US20120251948A1;US8846293B2;JP5572656B2;JP5775804B2。
还已探索了浸没式光刻来扩展光致抗蚀剂分辨率。在浸没式光刻中,通过使用流体以使更多的光聚集在抗蚀剂膜中来增加曝光工具镜片的数值孔径。更具体地说,浸没式光刻在成像装置(例如ArF步进器)的最后一个表面与晶片或其它衬底上第一个表面之间使用相对高折射率流体。
电子装置制造商不断地寻求分辨率增加的图案化光致抗蚀剂图像。所期望的是具有可提供增强的成像能力的新型光致抗蚀剂组合物。
发明内容
在一个方面中,现提供新型单体和聚合物以及包含这类聚合物的光致抗蚀剂。
在优选方面中,提供包含有包含碳脂环基或杂脂环基的重复单元的聚合物,所述基团包含1)一个或多个酸不稳定环取代基和2)一个或多个任选被取代的醚化(醚)或硫醚化(硫醚)环取代基。在某些优选方面中,1)酸不稳定环取代基是酯基,并且2)碳脂环基或杂脂环基的碳环原子是酸不稳定酯基的季碳。
碳脂环基或杂脂环基的醚环取代基宜可以是各个部分,如相同或不同的任选被取代的烷氧基,包括可包含1、2、3个或更多个氧原子的任选被取代的C1-20烷氧基,如甲氧基(-OCH3);和任选被取代的芳氧基,如任选被取代的碳环芳氧基,例如任选被取代的苯氧基(-OC6H5)。
碳脂环基或杂脂环基的硫醚环取代基宜可以是各个部分,如相同或不同的任选被取代的硫代烷基,包括可包含1、2、3个或更多个硫原子的任选被取代的C1-20硫代烷基,如甲基硫醚(-SCH3);和任选被取代的芳基硫醚基,如任选被取代的碳环芳基硫醚,例如任选被取代的苯基硫醚(-SC6H5)。
在一优选方面中,聚合物可包含下式(I)或(I')中的任一个或两个的结构:
其中在式(I)中:
X和Y独立地是C、O或S并且形成碳脂环族环或杂脂环族环(X或Y中的一个是杂原子特别是O或S的杂脂环族环);
R是非氢取代基,如任选被取代的烷基(例如,任选被取代的C1-20烷基,包括环烷基)、任选被取代的杂烷基(例如,任选被取代的C1-20烷氧基)和任选被取代的碳环芳基(如任选被取代的苯基);
R1是任选被取代的醚或任选被取代的硫醚;
R2是非氢取代基,如烷基酯(例如,C1-20烷基酯,例如-CH3C(=O)O-、-CH3CH2C(=O)O-);
m是0(其中不存在R2基团)或更大的整数整数;
n是正整数(例如,1、2、3、4、5或6);并且m和n的总和不超过碳脂环族环或杂脂环族环的可用价;
其中在式(I')中:
X和Y独立地是C、O或S并且形成碳脂环族环或杂脂环族环(X或Y中的一个是杂原子特别是O或S的杂脂环族环);
R是非氢取代基,如任选被取代的烷基(例如,任选被取代的C1-20烷基,包括环烷基)、任选被取代的杂烷基(例如,任选被取代的C1-20烷氧基)和任选被取代的碳环芳基(如任选被取代的苯基);
R1是任选被取代的醚或任选被取代的硫醚;
R2是非氢取代基,如烷基酯(例如,C1-20烷基酯,例如-CH3C(=O)O-、-CH3CH2C(=O)O-);
m是0(其中不存在R2基团)或更大的整数整数;
n是正整数(例如,1、2、3、4、5或6);并且m和n的总和不超过碳脂环族环或杂脂环族环的可用价。
在一优选方面中,聚合物可包含下式(IA)的结构:
其中在式(IA)中,
所描绘的环基是碳脂环基,例如具有5到20个碳环原子,优选5或6个碳环原子;并且
R、R1、R2、m和n与上文式(I)中所定义相同。
在一尤其优选方面中,聚合物可包含下式(II)的结构:
其中:
R、R1、R2、m和n与上文式(I)中所定义相同。
在上文式(I)、(I')、(IA)和(II)中,在式结构的顶部的所描绘的波浪线表示化学键,如附接到连接到聚合物主链的基团的附接键,或波浪线描绘为聚合物主链的一部分的化学键或化学连接(例如,-CH2-)。
本发明的聚合物可包含多个不同的重复单元。因此,本发明聚合物可以是均聚物,或更通常是共聚物、三元聚合物、四元聚合物、五元聚合物或其它具有2、3、4、5个或更多个不同重复单元的更高级聚合物。这类额外重复单元无需包含有包含碳脂环基或杂脂环基的结构,所述基团包含1)一个或多个酸不稳定环取代基和2)一个或多个醚或硫醚环取代基,前提是聚合物的至少一个单元包含具有被取代的碳脂环基的这类结构。下文实例描绘优选的额外聚合物单元。
本发明的尤其优选聚合物可包含聚合丙烯酸酯单元。在一相关实施例中,优选的聚合物包含通过使下式(III)、(III')、(IIIA)和(IIIB)中的任一个的一种或多种单体聚合来获得的单元:
其中在式(III)和(III')中:Y'是氢或任选被取代的烷基,如任选被取代的C1-6烷基,包括甲基;并且X、Y、R、R1、R2、m和n与式(I)中所定义相同。
其中在式(III')中:Y'是氢或任选被取代的烷基,如任选被取代的C1-6烷基,包括甲基;并且X、Y、R、R1、R2、m和n与式(I')中所定义相同。
其中在式(IIIa)中:Y'是氢或任选被取代的烷基,如任选被取代的C1-6烷基,包括甲基;并且R、R1、R2、m和n与式(IA)中所定义相同。
其中在式(IIIB)中:Y'是氢或任选被取代的烷基,如任选被取代的C1-6烷基,包括甲基;并且R、R1、R2、m和n与式(II)中所定义相同。
还提供包含一或多种酸产生剂和一种或多种如本文所公开的聚合物的光致抗蚀剂,所述一种或多种聚合物包含有包含碳脂环基或杂脂环基的结构,所述基团包含1)一个或多个酸不稳定环取代基和2)一个或多个醚或硫醚环取代基,所述一种或多种聚合物包括包含如上文所公开的式(I)、(I')、(IA)、(II)、(III)、(III')、(IIIA)和(IIIB)的结构的聚合物。在优选方面中,本发明的光致抗蚀剂可包含第二聚合物,其不同于包含有包含碳脂环基或杂脂环基的结构的聚合物,所述基团包含1)一个或多个酸不稳定环取代基和2)一个或多个醚或硫醚环取代基。包含有包含1)一个或多个酸不稳定环取代基和2)一个或多个醚或硫醚环取代基的碳脂环基或杂脂环基的聚合物(如上文式(I)、(I')、(IA)、(II)、(III)、(III')、(IIIA)和(IIIB)的结构,在本文中有时被称作光致抗蚀剂组合物的“第一聚合物”或“主要聚合物”。在某些优选方面中,本发明光致抗蚀剂可包含不同于第一或主要聚合物的额外聚合物(在本文中有时被称作光致抗蚀剂组合物的“第二聚合物”)。第二聚合物可任选地包含酸不稳定基团。如下文进一步论述,在某些实施例中,第一和第二聚合物可具有不同表面能。
在某些优选方面中,第一聚合物可进一步包含第三单元,所述第三单元(1)包含一个或多个疏水基团和(2)包含有包含碳脂环基或杂脂环基的结构的重复单元,所述基团包含1)一个或多个酸不稳定环取代基和2)一个或多个醚或硫醚环取代基(如上文式(I)、(I')、(IA)、(II)、(III)、(III')、(IIIA)和(IIIB)的结构。适合地,这类一个或多个疏水基团各自包含3、4、5、6、7、8个或更多个碳原子,如具有这类碳原子数的任选被取代的烷基或烷氧基。
还提供处理光致抗蚀剂组合物的方法,其可适合地包含在衬底上涂覆如本文所公开的光致抗蚀剂组合物层;使光致抗蚀剂组合物层曝光于活化辐射;以及使曝光的光致抗蚀剂组合物显影,从而得到光致抗蚀剂浮雕图像。适合地,光致抗蚀剂组合物层可被浸没式曝光。干式(非浸没式)曝光也将是适合的。在某些方面中,注入和EUV光刻工艺也是优选的。
在一优选方面中,用显影剂去除光致抗蚀剂层的未曝光部分,在一个或多个待图案化层上留下光致抗蚀剂图案。逐图案曝光可通过浸没式光刻或替代地使用干式曝光技术进行。
根据另一方面,提供涂布的衬底。涂布的衬底包含衬底和在衬底表面上方的本发明的光致抗蚀剂组合物层。
还提供通过所公开的方法形成的电子装置,包括通过所公开的负性显影工艺形成的装置。
还提供包含有包含碳脂环基或杂脂环基的结构的结构的单体,所述基团包含1)一个或多个酸不稳定环取代基和2)一个或多个醚或硫醚环取代基。优选的单体包含上文式(I)、(I')、(IA)、(II)、(III)、(III')、(IIIA)和(IIIB)的结构。
如本文所使用,除非另外明确地或在上下文中指明,否则冠词“一(a和an)”包括一个或多个/一种或多种。
本发明的其它方面公开于下文中。
具体实施方式
如上文所论述,优选的聚合物和单体可包含式(I)、(I')、(IA)、(II)、(III)、(III')、(IIIA)和/或(IIIB)的结构,如那些式子在上文阐述。在那些式(I)、(I')、(IA)、(II)、(III)、(III')、(IIIA)和/或(IIIB)中,为任选被取代的醚的优选R1基团可以是各个部分,如相同或不同的任选被取代的烷氧基,包括可包含1、2、3个或更多个氧原子的任选被取代的C1-20烷氧基,如甲氧基(-OCH3);和任选被取代的芳氧基,如任选被取代的碳环芳氧基,例如任选被取代的苯氧基(-OC6H5)。在那些式(I)、(I')、(IA)、(II)、(III)、(III')、(IIIA)和/或(IIIB)中,为任选被取代的硫醚的优选R1基团宜可以是各个部分,如相同或不同的任选被取代的硫代烷基,包括可包含1、2、3个或更多个硫原子的任选被取代的C1-20硫代烷基,如甲基硫醚(-SCH3);和任选被取代的芳基硫醚基团,如任选被取代的碳环芳基硫醚,例如任选被取代的苯基硫醚(-SC6H5)。
如所论述,在某些优选方面中,本发明的光致抗蚀剂可包含至少两种不同聚合物:1)包含碳脂环基或杂脂环基的第一聚合物(主要聚合物),所述基团包含a)一个或多个酸不稳定环取代基和b)一个或多个醚或硫醚环取代基(如式(I)、(I')、(IA)、(II)、(III)、(III')、(IIIA)和(IIIB)的结构;和2)不同于第一聚合物的第二聚合物。第二聚合物无需含有包含a)一个或多个酸不稳定环取代基和b)一个或多个醚或硫醚环取代基的碳脂环基或杂脂环基。在优选的组合物中,在涂布光致抗蚀剂组合物期间,第一聚合物或第二聚合物可朝向抗蚀剂涂层的上表面迁移。在某些系统中,这可形成大体上由迁移第一聚合物或第二聚合物组成的表面层。在某些优选的组合物中,在涂布光致抗蚀剂组合物期间,第二聚合物朝向抗蚀剂涂层的上表面迁移。在曝光和曝光后烘烤(PEB)之后,可使抗蚀剂涂层显影,包括在包含有机溶剂的显影剂中。如果使用有机显影剂,那么这类显影剂去除光致抗蚀剂层的未曝光区域和曝光区域的表面层。也可以使用去除抗蚀剂涂层的曝光区域的水性碱性显影剂。当在干式光刻或浸没式光刻工艺中使用组合物时,可获得本发明光致抗蚀剂组合物的优点。当用于浸没式光刻时,优选的光致抗蚀剂组合物可进一步呈现光致抗蚀剂材料对浸没流体的迁移(浸滤)(也是添加剂聚合物迁移到抗蚀剂表面的结果)降低。显然,这可以在不在光致抗蚀剂上使用顶涂层的情况下实现。
如上文所论述,各种物质和取代基(包括式(I)、(I')、(IA)、(II)、(III)、(III')、(IIIA)和(IIIB)的基团,其可以是“任选被取代的”,宜可以在一个或多个可用的位置被例如以下取代:卤素(F、Cl、Br、I);氰基;硝基;羟基;氨基;烷基,如C1-20烷基或C1-8烷基;烯基,如C2-8烯基;烷氨基,如C1-20烷氨基或C1-8烷氨基;硫代烷基,如C1-20硫代烷基或C1-8硫代烷基;碳环芳基,如苯基、萘基、蒽基等;等等。
光致抗蚀剂可在各种辐射波长下使用,例如小于400nm、小于300nm或小于200nm的波长,或其中248nm、193nm和EUV(例如13.5nm)曝光波长是优选的。组合物可进一步用于电子束(E-beam)曝光工艺。本发明的光致抗蚀剂组合物优选是化学增幅型材料。
优选的单体(包括式(III)、(III')、(IIIA)和/或(IIIB)的优选单体包括以下单体:其可任选地与一种或多种其它单体反应以形成如本文所公开的优选聚合物((包括式(I)、(I')、(IA)和/或(II)的优选聚合物:
可易于制备包含有包含以下的碳脂环基或杂脂环基的单体和聚合物:1)一个或多个酸不稳定环取代基和2)一个或多个醚或硫醚环取代基。举例来说,包含环酮基的碳脂环基或杂脂环基可与格林纳试剂(Grignard reagent)反应以提供具有季环碳的碳脂环基,其中一个或这类碳环原子取代基是羟基部分。羟基可进一步按需要官能化,如通过与卤化酰基反应,以提供丙烯酸酯单体。这类单体可反应,包括与一种或多种不同的其它单体反应以制备所期望的聚合物。参见例如以下实例1到7。
包含有包含1)一个或多个酸不稳定环取代基和2)一个或多个醚或硫醚环取代基的碳脂环基或杂脂环基的聚合物可与这类单体反应以提供均聚物,或与其它不同化合物反应以提供更高级聚合物,如共聚物(至少两个不同重复单元)、三元共聚物(三个不同重复单元)、四元共聚物(四个不同重复单元)或五元共聚物(五个不同重复单元)。可按需要使用引发剂化合物。关于例示性优选合成,参见以下实例8到11。
在光致抗蚀剂组合物中,在优选聚合物的情况下,包含有包含1)一个或多个酸不稳定环取代基和2)一个或多个醚或硫醚环取代基的碳脂环基或杂脂环基的聚合物重复单元可充当酸不稳定基团,并且在光刻工加期间,特别在软烘烤、曝光于活化辐射和曝光后烘烤之后,在由光酸和/或热酸产生剂产生的酸存在下经历脱保护反应。这由光酸诱导的酸不稳定基团裂解产生,引起聚合物的极性变化。
聚合物还可包含一个或多个额外酸不稳定基团,其可例如选自叔烷基碳酸酯、叔烷基酯、叔烷基醚、缩醛和缩酮。优选地,酸不稳定基团是酯基,其含有共价连接到第二基质聚合物的酯的羧基氧的叔非环状烷基碳或叔脂环族碳。所述酸不稳定基团的裂解引起羧酸基团的形成。适合的含有酸不稳定基团的单元包括例如酸不稳定(烷基)丙烯酸酯单元,如(甲基)丙烯酸叔丁酯、(甲基)丙烯酸1-甲基环戊酯、(甲基)丙烯酸1-乙基环戊酯、(甲基)丙烯酸1-异丙基环戊酯、(甲基)丙烯酸1-丙基环戊基酯、(甲基)丙烯酸1-甲基环己酯、(甲基)丙烯酸1-乙基环己酯、(甲基)丙烯酸1-异丙基环己酯、(甲基)丙烯酸1-丙基环己酯、叔丁基甲基金刚烷基(甲基)丙烯酸酯、(甲基)丙烯酸乙基葑酯等等,以及其它环状(包括脂环)和非环状(烷基)丙烯酸酯。缩醛和缩酮酸不稳定基团还可在碱溶性基团如羧基或羟基的末端处被氢原子取代,以便与氧原子键结。当产生酸时,酸裂解缩醛或缩酮基团与缩醛型酸可离解的溶解抑制基团所键结的氧原子之间的键。例示性的这类酸不稳定基团描述于例如美国专利案第US6057083号、第US6136501号和第US8206886号以及欧洲专利公开案第EP01008913A1号和第EP00930542A1号中。同样适合的是作为糖衍生物结构的一部分的缩醛和缩酮基团,其裂解将引起羟基的形成,例如美国专利申请第US2012/0064456A1号中描述的那些。
为用于在某些小于200nm波长如193nm下成像的光致抗蚀剂中,包含有包含1)一个或多个酸不稳定环取代基和2)一个或多个醚或硫醚环取代基的碳脂环基或杂脂环基的聚合物通常基本上不含(例如,小于15摩尔%)、优选地完全不含苯基、苯甲基或其它芳香族基团,其中这类基团高度吸收辐射。
本发明聚合物可包含各个单元,包括例如含有非芳香族环烯烃(内环双键)(如任选被取代的降冰片烯)的聚合单元的那些,例如美国专利第5,843,624号和第6,048,664号中所描述的聚合物。另外其它适合的聚合物单元包括聚合酐单元,特别地聚合马来酸酐和/或衣康酸酐单元,如公开于欧洲公开申请EP01008913A1和美国专利第6,048,662号中。
在小于200nm波长如193nm和EUV(例如,13.5nm)的情况下,本发明聚合物可包括含有内酯部分的单元,以用于控制聚合物和光致抗蚀剂组合物的溶解速率。用于含有内酯部分的聚合物中的适合的单体包括例如以下:
包含有包含1)一个或多个酸不稳定环取代基和2)一个或多个醚或硫醚环取代基的碳脂环基或杂脂环基的聚合物还可以含有如下重复单元:其增强聚合物和光致抗蚀剂组合物的耐蚀刻性,并且提供控制聚合物和光致抗蚀剂组合物的溶解速率的额外手段。用于形成这类单元的单体包括例如具有额外碳脂环基(包括桥连或多环基团)的那些单体,如以下:
在优选方面中,与下文所描述的第一或添加剂聚合物的表面能相比,包含有包含1)一个或多个酸不稳定环取代基和2)一个或多个醚或硫醚环取代基的碳脂环基或杂脂环基的聚合物具有更高的表面能,并且应与第一聚合物基本上不可混溶。作为表面能不同的结果,可在旋涂期间进行所述聚合物与第一聚合物的分离。第二或基质聚合物的适合的表面能通常是20到50mN/m,优选30到40mN/m。
包含有包含1)一个或多个酸不稳定环取代基和2)一个或多个醚或硫醚环取代基的碳脂环基或杂脂环基的聚合物以足以使抗蚀剂的曝光涂层可在适合的显影剂溶液中显影的量存在于抗蚀剂组合物中。通常,聚合物以按抗蚀剂组合物的总固体计50wt%到95wt%的量存在于组合物中。聚合物的重量平均分子量通常小于100,000,例如是3000到100,000,更通常3000到15,000。上文所描述的聚合物中的两种或更多种的掺合物可适合地用于本发明的光致抗蚀剂组合物中。
可另外用于光致抗蚀剂组合物中的第一聚合物优选地是如下物质:与包含有包含1)一个或多个酸不稳定环取代基和2)一个或多个醚或硫醚环取代基的碳脂环基或杂脂环基的聚合物的表面能相比,具有更低的表面能,并且优选地与第二聚合物基本上不可混溶。以这种方式,促进第一聚合物在涂布过程期间向所涂覆的光致抗蚀剂层的顶部或上部部分的偏析或迁移。虽然第一聚合物的所期望的表面能将取决于特别的主要聚合物和其表面能,但第一聚合物表面能通常是18到40mN/m,优选地20到35mN/m并且更优选29到33mN/m。虽然第一聚合物在涂布过程期间迁移到抗蚀剂层的上表面,但优选的是,在第一聚合物与就在抗蚀剂层表面下方的主要聚合物之间存在一些互混。相信这类互混有助于通过降低或消除由杂散光引起的第二或基质聚合物附近的黑暗区域中产生的酸来降低抗蚀剂层中的表面抑制。互混程度将例如取决于主要聚合物与第一或添加剂聚合物(AP)之间的表面能(SE)的差值(ΔSE=SEMP-SEAP)。对于既定第一或主要聚合物,互混程度可随着ΔSE降低而增加。ΔSE通常是2到32mN/m,优选是5到15mN/m。
第一聚合物优选地不含硅。含硅聚合物与某些蚀刻剂中的有机光致抗蚀剂聚合物相比呈现显著较低的蚀刻速率。因此,含硅第一聚合物聚集在基于有机第二聚合物的抗蚀剂层的表面可在刻蚀过程期间引起锥孔缺陷。第一聚合物可含有氟或可不含氟。优选的第一聚合物在用于调配光致抗蚀剂组合物的相同的有机溶剂中是可溶的。优选的第一聚合物在用于负性显影工艺的有机显影剂中也将是可溶的或在曝光后烘烤(例如120℃持续60秒)之后即变得可溶。
适合的第一聚合物公开于美国专利7968268中,但将优选地包含有包含1)一个或多个酸不稳定环取代基和2)一个或多个醚或硫醚环取代基的碳脂环基或杂脂环基。针对可在特别适用于浸没式光刻的多种聚合物光致抗蚀剂组合物中用作第一或主要聚合物的优选聚合物,还参见以下实例。。
本发明光致抗蚀剂组合物优选地可包含一种或多种光酸产生剂(PAG),其以在曝光于活化辐射时足以在光致抗蚀剂组合物的涂层中产生潜像的量采用。举例来说,按光致抗蚀剂组合物的总固体计,光酸产生剂将宜以约1到20wt%的量存在。通常,较小量的光敏性组分将适用于化学增幅型抗蚀剂。
适合的PAG为化学增幅型光致抗蚀剂领域中已知的并且包括例如:鎓盐,例如三苯基锍三氟甲烷磺酸盐、(对叔丁氧基苯基)二苯基锍三氟甲烷磺酸盐、三(对叔丁氧基苯基)锍三氟甲烷磺酸盐、三苯基锍对甲苯磺酸盐;硝基苯甲基衍生物,例如2-硝基苯甲基-对甲苯磺酸盐、2,6-二硝基苯甲基-对甲苯磺酸盐和2,4-二硝基苯甲基-对甲苯磺酸盐;磺酸酯,例如1,2,3-三(甲烷磺酰基氧基)苯、1,2,3-三(三氟甲烷磺酰基氧基)苯和1,2,3-三(对甲苯磺酰基氧基)苯;重氮甲烷衍生物,例如双(苯磺酰基)重氮甲烷、双(对甲苯磺酰基)重氮甲烷;乙二肟衍生物,例如双-O-(对甲苯磺酰基)-α-二甲基乙二肟和双-O-(正丁烷磺酰基)-α-二甲基乙二肟;N-羟基酰亚胺化合物的磺酸酯衍生物,例如N-羟基丁二酰亚胺甲磺酸酯、N-羟基丁二酰亚胺三氟甲磺酸酯;和含卤素三嗪化合物,例如2-(4-甲氧基苯基)-4,6-双(三氯甲基)-1,3,5-三嗪和2-(4-甲氧基萘基)-4,6-双(三氯甲基)-1,3,5-三嗪。可使用这类PAG中的一种或多种。
用于本发明的光致抗蚀剂组合物的适合溶剂包括例如:二醇醚,如2-甲氧基乙基醚(二乙二醇二甲醚)、乙二醇单甲醚和丙二醇单甲醚;丙二醇单甲基醚乙酸酯;乳酸酯,如乳酸甲酯和乳酸乙酯;丙酸酯,例如丙酸甲酯、丙酸乙酯、乙氧基丙酸乙酯和甲基-2-羟基异丁酸酯;溶纤剂酯,如溶纤剂乙酸甲酯;芳香族烃,如甲苯和二甲苯;以及酮,如甲基乙基酮、环己酮以及2-庚酮。溶剂掺合物,如上文所述的溶剂中的两种、三种或更多种的掺合物也是适合的。按光致抗蚀剂组合物的总重量计,溶剂通常以90到99wt%、更通常95到98wt%的量存在于组合物中。
其它用于光致抗蚀剂组合物的任选的添加剂包括例如光化和对比染料、抗条纹剂、塑化剂、速度增强剂、敏化剂等等。如果使用,那么按光致抗蚀剂组合物的总固体计,这类任选的添加剂通常以较少量如0.1到10wt%存在于组合物中,但按光致抗蚀剂组合物的总固体计,填充剂和染料可以相对较大浓度例如5到30wt%存在。
本发明的抗蚀剂组合物的优选任选的添加剂是添加的碱,其可增强所显影的抗蚀剂浮雕图像的分辨率。适合的碱性淬灭剂包括例如:直链和环状酰胺和其衍生物,如N,N-双(2-羟乙基)棕榈酰胺、N,N-二乙基乙酰胺、N1,N1,N3,N3-四丁基丙二酰胺、1-甲基氮杂环庚烷-2-酮、1-烯丙基氮杂环庚烷-2-酮和及1,3-二羟基-2-(羟甲基)丙-2-基氨基甲酸叔丁酯;芳香族胺,如吡啶和二叔丁基吡啶;脂肪族胺,如三异丙醇胺、正叔丁基二乙醇胺、三(2-乙酰氧基-乙基)胺、2,2',2”,2”'-(乙烷-1,2-二基双(氮烷三基))四乙醇和2-(二丁基氨基)乙醇、2,2',2”-氮基三乙醇;环状脂肪族胺,如1-(叔丁氧基羰基)-4-羟基哌啶、1-吡咯烷甲酸叔丁酯、2-乙基-1H-咪唑-1-甲酸叔丁酯、哌嗪-1,4-二甲酸二叔丁酯和N(2-乙酰氧基-乙基)吗啉。这些碱性淬灭剂中,优选1-(叔丁氧基羰基)-4-羟基哌啶和三异丙醇胺。所添加的碱适宜以相对较小量(例如相对于PAG,1到20wt%,更通常相对于PAG,5到15wt%)使用。
根据本发明使用的光致抗蚀剂通常根据已知程序制备。举例来说,本发明的抗蚀剂可以通过将光致抗蚀剂的组分溶解于适合的溶剂中而以涂层组合物形式制备,所述溶剂例如是以下各项中的一种或多种:二醇醚,如2-甲氧基乙基醚(二乙二醇二甲醚)、乙二醇单甲醚、丙二醇单甲醚;丙二醇单甲基醚乙酸酯;乳酸酯,如乳酸乙酯或乳酸甲酯,其中乳酸乙酯是优选的;丙酸酯,确切地说丙酸甲酯、丙酸乙酯和乙氧基丙酸乙酯;溶纤剂酯,如溶纤剂乙酸甲酯;芳香族烃,如甲苯或二甲苯;或酮,如甲基乙基酮、环己酮和2-庚酮。光致抗蚀剂的所期望的总固体含量将取决于如组合物中的特定聚合物、最终层厚度以及曝光波长的因素。通常,按光致抗蚀剂组合物的总重量计,光致抗蚀剂的固体含量在1到10wt%、更通常2到5wt%范围内变化。
本发明进一步提供用于形成光致抗蚀剂浮雕图像和使用本发明的光致抗蚀剂制造电子装置的方法。本发明还提供新型制品,其包含涂有本发明的光致抗蚀剂组合物的衬底。
在光刻加工中,可在多种衬底上涂覆光致抗蚀剂组合物。所述衬底可具有以下材料:如半导体,如硅或化合物半导体(例如,III-V或II-VI);玻璃;石英;陶瓷;铜等等。通常,衬底是半导体晶片,如单晶硅或化合物半导体晶片,并且可具有形成于其表面上的一个或多个层和图案化特征。可在衬底上提供一个或多个待图案化的层。任选地,下伏基底衬底材料本身可被图案化,例如当期望在衬底材料中形成沟槽时。在对基底衬底材料自身图案化的情况下,图案应被认为形成于衬底的层中。
层可包括例如一个或多个导电层,如铝、铜、钼、钽、钛、钨、合金、这类金属的氮化物或硅化物、掺杂非晶硅或掺杂多晶硅的层;一个或多个介电层,如氧化硅、氮化硅、氮氧化硅或金属氧化物的层;半导体层,如单晶硅,以及其组合。待蚀刻的层可由各种技术形成,所述技术例如化学气相沉积(CVD),如等离子体增强型CVD、低压CVD或外延生长;物理气相沉积(PVD),如溅镀或蒸镀,或电镀。待蚀刻的一个或多个层102的特定厚度将取决于材料和形成的特定装置而变化。
取决于待蚀刻的特定层、膜厚度和待使用的光刻材料和工艺,可能期望在层上安置硬掩模层和/或底部抗反射涂层(BARC),在其上涂布光致抗蚀剂层。使用硬掩模层可能例如在极薄抗蚀剂层的情况下是所期望的,其中待蚀刻的层需要显著蚀刻深度,和/或其中特定蚀刻剂具有不良抗蚀剂选择性。当使用硬掩模层时,待形成的抗蚀剂图案可转移到硬掩模层,其转而可按蚀刻下伏层的掩模形式使用。适合的硬掩模材料和形成方法是所属领域中已知的。典型的材料包括例如钨、钛、氮化钛、氧化钛、氧化锆、氧化铝、氮氧化铝、氧化铪、非晶碳、氮氧化硅和氮化硅。硬掩模层可包括单个层或不同材料的多个层。硬掩模层可例如通过化学或物理气相沉积技术形成。
当衬底和/或下伏层将在光致抗蚀剂曝光期间另外反射大量入射辐射,使得形成的图案的质量将受不利影响时,底部抗反射涂层可为合意的。这类涂层可改进聚焦深度、曝光宽容度、线宽均匀性和CD控制。抗反射涂层通常用于抗蚀剂曝光于深紫外光(300nm或更小),例如KrF准分子激光(248nm)或ArF准分子激光(193nm)的情况下。抗反射涂层可包含单个层或多个不同层。适合的抗反射材料和形成方法在所属领域中已知。抗反射材料是可商购的,例如由Rohm and Haas Electronic Materials LLC(美国马萨诸塞州马波罗(Marlborough,MA USA))以ARTM商标销售的那些,如ARTM40A和ARTM124抗反射材料。
将由如上文所描述的本发明组合物形成的光致抗蚀剂层涂覆到衬底上。光致抗蚀剂组合物通常通过旋涂涂覆到衬底。在旋涂期间,在如本文所公开的包含第一和第二聚合物的抗蚀剂组合物中,光致抗蚀剂中的第一聚合物分离到所形成的抗蚀剂层的上表面,其通常与紧靠上表面并且位于上表面下方的区域中的第二聚合物互混。涂布溶液的固体含量可基于所使用的具体涂布设备、溶液的粘度、涂布工具的速度和允许旋转的时间量进行调节以提供所期望的膜厚度。光致抗蚀剂层的典型厚度是约500到
随后可软烘烤光致抗蚀剂层以使层中的溶剂含量降到最低,由此形成无粘性涂层并且改善层与衬底的粘着。软烘烤可在加热板上或烘箱中进行,其中加热板是典型的。软烘烤温度和时间将取决于例如光致抗蚀剂的特定材料和厚度。典型的软烘烤在约90℃到150℃的温度和约30到90秒的时间下进行。
随后通过光掩模将光致抗蚀剂层适合地曝光于活化辐射以在曝光区域与未曝光区域之间产生溶解度差异。本文中提及将光致抗蚀剂组合物曝光于使组合物活化的辐射指示辐射能够在光致抗蚀剂组合物中形成潜像。光掩模具有对应于抗蚀剂层的区域的光学透明区和光学不透明区以在后续显影步骤中分别保留和去除。曝光波长通常小于400nm、小于300nm或小于200nm,其中248nm、193nm和EUV波长是典型的。光致抗蚀剂材料可进一步用于电子束曝光的情况。所述方法应用于浸没式或干式(非浸没式)光刻技术中。曝光能量通常是约10到80mJ/cm2,其取决于曝光工具和光敏组合物的组分。
在光致抗蚀剂层曝光后,进行曝光后烘烤(PEB)。PEB可例如在加热板上或烘箱中进行。PEB的条件将取决于例如特定光致抗蚀剂组合物和层厚度。PEB通常在约80到150℃的温度和约30到90秒的时间下进行。在光致抗蚀剂中形成由极性切换与非切换区域(分别对应于曝光区域和未曝光区域)之间的边界(虚线)界定的潜像。相信在曝光后烘烤期间脱保护的第一聚合物的碱性部分(例如胺)可防止光致抗蚀剂层的黑暗区域中的极性切换,黑暗区域中可能存在杂散或散射光,产生具有垂直壁的潜像。这是由黑暗区域中PAG产生的酸的中和的结果。因此,可基本上防止这些区域中酸不稳定基团的裂解。
随后适合地使曝光的光致抗蚀剂层显影以去除光致抗蚀剂层的未曝光区域。可使用水性碱性显影剂,如烷基铵水性显影剂。显影剂还可以是有机显影剂,例如选自酮、酯、醚、烃和其混合物的溶剂。适合的酮溶剂包括例如丙酮、2-己酮、5-甲基-2-己酮、2-庚酮、4-庚酮、1-辛酮、2-辛酮、1-壬酮、2-壬酮、二异丁基酮、环己酮、甲基环己酮、苯基丙酮、甲基乙基酮和甲基异丁基酮。适合的酯溶剂包括例如乙酸甲酯、乙酸丁酯、乙酸乙酯、乙酸异丙酯、乙酸戊酯、丙二醇单甲醚乙酸酯、乙二醇单乙醚乙酸酯、二乙二醇单丁醚乙酸酯、二乙二醇单乙醚乙酸酯、乙基-3-乙氧基丙酸酯、乙酸3-甲氧基丁酯、乙酸3-甲基-3-甲氧基丁酯、甲酸甲酯、甲酸乙酯、甲酸丁酯、甲酸丙酯、乳酸乙酯、乳酸丁酯和乳酸丙酯。适合的醚溶剂包括例如二恶烷、四氢呋喃和二醇醚溶剂,例如乙二醇单甲醚、丙二醇单甲醚、乙二醇单乙醚、丙二醇单乙醚、二乙二醇单甲醚、三乙二醇单乙醚和甲氧基甲基丁醇。适合的酰胺溶剂包括例如N-甲基-2-吡咯烷酮、N,N-二甲基乙酰胺和N,N-二甲基甲酰胺。适合的烃溶剂包括例如芳香族烃溶剂,如甲苯和二甲苯。另外,可使用这些溶剂的混合物,或与除上文所述的那些以外的溶剂混合或与水混合的所列溶剂中的一种或多种。其它适合的溶剂包括用于光致抗蚀剂组合物中的那些。显影剂优选是2-庚酮或乙酸丁酯,如乙酸正丁酯。
通常通过旋涂将显影剂涂覆到衬底。显影时间是可有效去除光致抗蚀剂的未曝光区域的时段,其中5到30秒的时间是典型的。显影通常在室温下进行。可在显影后不使用清洁冲洗的情况下进行显影工艺。在这一方面,已发现显影工艺可产生无残余物的晶片表面,使得无需这类额外冲洗步骤。
BARC层如果存在,那么使用抗蚀剂图案作为蚀刻掩模来选择性蚀刻,暴露下伏硬掩模层。随后选择性蚀刻硬掩模层,再使用抗蚀剂图案作为蚀刻掩模,产生图案化BARC和硬掩模层。用于蚀刻BARC层和硬掩模层的适合的蚀刻技术和化学物质在所属领域中已知并且将取决于例如这些层的特定材料。干式蚀刻工艺,如反应性离子蚀刻是典型的。随后使用已知技术,例如氧等离子体灰化从衬底去除抗蚀剂图案和图案化BARC层。
以下非限制性实例说明本发明。
以下非限制性实例说明本发明。
实例1-7:合成单体
实例1:合成甲基丙烯酸1-乙基-4-甲氧基环己酯(EMCHMA)
步骤1.在500ml圆底烧瓶A中将36ml的EtMgBr溶液(3M于乙醚中)添加到100ml无水甲苯中。将12.6g的4-甲氧基环己-1-酮溶解于13ml THF中。在0℃下历经1小时将制备的THF溶液逐滴添加到圆底烧瓶A中。在0℃下搅拌反应混合物2小时。将50ml水性NH4Cl缓慢添加到烧瓶A中。用CH2Cl2萃取反应混合物。所萃取的有机相用Na2SO4干燥并且在真空中蒸发。通过柱色谱纯化粗产物,得到最终产物,即产率是52%的1-乙基-4-甲氧基环己-1-醇(8.24g)。1H NMR(600MHz,CDCl3):δ(ppm)3.39(m,0.4H),3.36~3.31(m,3H),3.13(M,0.6H),1.82(m,2H),1.82~1.60(m,5H),1.55~1.45(m,2H),1.40~1.30(m,2H),0.93(t,3H)。
步骤2.将8.24g的1-乙基-4-甲氧基环己-1-醇溶解于103ml的CH2Cl2中。直接添加15.88ml的TEA。在0℃下缓慢添加6.01ml甲基丙烯酰氯并且在室温下搅拌4小时。连续添加20ml水和20ml的HCl水溶液(6N)。用100ml的MC萃取反应混合物。将收集的有机层用100ml水性NaHCO3中和两次,用Na2SO4干燥,并且在真空中蒸发。通过柱色谱纯化粗产物,得到最终产物,即产率是60%的甲基丙烯酸1-乙基-4-甲氧基环己酯(EMCHMA)(7.08g)。1H NMR(600MHz,CDCl3):δ6.06~6.04(m,1H),5.50(s,1H),3.42(m,0.4H),3.35~3.31(m,3H),3.18(M,0.6H),2.42(m,1H),2.09(m,1H),1.96~1.90(m,6H),1.68~1.57(m,6H),1.45(m,1H),1.32(m,1H),1.29(m,1H),0.85(t,3H)。
实例2:合成甲基丙烯酸4-甲氧基-1-甲基环己酯(MMCHMA)
步骤1.在500ml圆底烧瓶A中将48ml的MeMgBr溶液(3M于乙醚中)添加到140ml无水甲苯中。将17.0g的4-甲氧基环己-1-酮溶解于30ml的THF中。在0℃下历经1小时将制备的THF溶液逐滴添加到圆底烧瓶A中。在0℃下搅拌反应混合物2小时。将110ml水性NH4Cl缓慢添加到烧瓶A中。用CH2Cl2萃取反应混合物。萃取的有机相用Na2SO4干燥并且在真空中蒸发。通过柱色谱纯化粗产物,得到最终产物,即产率是71%的4-甲氧基-1-甲基环己-1-醇(13.7g)。1H NMR(600MHz,CDCl3):δ(ppm)3.35(m,2H),3.32(s,1.43H),3.13(m,0.5H),1.82(m,2H),1.70(m,2H),1.61(m,2H),1.44(m,2H),1.16(d,3H)。
步骤2.将13.7g的4-甲氧基-1-甲基环己-1-醇溶解于200ml的CH2Cl2中。直接添加28.9ml的TEA。在0℃下缓慢添加11.13ml的甲基丙烯酰氯并且在室温下搅拌16小时。连续添加150ml水、50ml水性NH4Cl和20ml的HCl水溶液(6N)。用200ml的MC萃取反应混合物。将收集的有机层用100ml水性NaHCO3中和两次,用Na2SO4干燥,过滤,并且在真空中蒸发。通过柱色谱纯化粗产物,得到最终产物,即产率是73%的甲基丙烯酸4-甲氧基-1-甲基环己酯(MMCHMA)。1H NMR(600MHz,CDCl3):δ6.05~6.03(m,1H),5.50(s,1H),3.41(m,0.44H),3.35~3.31(m,3H),3.18(M,0.56H),2.39(m,1H),2.06(m,1H),1.92(s,3H),1.86(m,1H),1.80~1.55(m,3H),1.53(s,3H),1.47(m,1H),1.45(m,3H)。
实例3:合成甲基丙烯酸1-乙基-环己酯(ECHMA)
用具有实例1步骤2的类似程序合成4-甲氧基环己-1-酮、甲基丙烯酸1-乙基-环己酯(ECHMA)。
实例4:合成甲基丙烯酸1-甲基环己酯(MCHMA)
用具有实例1步骤2的类似程序合成4-甲氧基环己-1-酮、甲基丙烯酸1-甲基环己酯(MCHMA)。
实例5:合成甲基丙烯酸3-乙基-6-甲氧基四氢-2H-吡喃-3-基酯
通过根据上文实例1的程序,但用6-甲氧基二氢-2H-吡喃-3(4H)-酮取代4-甲氧基环己-1酮,制备标题化合物甲基丙烯酸3-乙基-6-甲氧基四氢-2H-吡喃-3-基酯。
实例6:合成甲基丙烯酸3-乙基-6-甲氧基四氢-2H-硫代吡喃-3-基酯
通过根据上文实例1的程序,但用6-甲氧基二氢-2H-硫代吡喃-3(4H)-酮取代4-甲氧基环己-1-酮,制备标题化合物甲基丙烯酸3-乙基-6-甲氧基四氢-2H-硫代吡喃-3-基酯。
实例7:
通过根据上文实例1的程序,但用6-甲硫基环己-1-酮取代4-甲氧基环己-1-酮,制备标题化合物4-甲硫基-1-甲基环己基甲基丙烯酸酯。
实例8-11:聚合物合成
通用聚合程序显示于实例8到11中
在圆底烧瓶A中将一系列具有不同馈送比率(参见表1)的量的单体溶解于与7到3种乳酸乙酯(EL)和γ丁内酯(GBL)的组合物的11.3g混合溶剂中。在圆底烧瓶B中将0.51g二甲基-2,2'-偶氮双-2-甲基丙酸酯(来自Wako Specialty Chemicals的V-601偶氮引发剂)溶解于1.8g的混合EL和GBL溶液中。对50ml两颈圆底烧瓶C馈入10.8g的混合EL和BLS溶液。将烧瓶C中的这种溶剂用N2气体净化并且在温和搅拌下加热到80℃。将烧瓶B中的溶液缓慢添加到烧瓶A中的溶液中。在90分钟期间通过使用注射泵将这种混合溶液逐滴添加到烧瓶C中并且接着搅拌4小时。将反应混合物冷却到室温,并且MeOH和H2O以9:1重量百分比的337g溶剂混合物。过滤最终沉淀物并且干燥16小时,获得目标聚合物。
表1.用于聚合物合成的一系列单体的馈送比率
实例编号 | MCHMA | ECHMA | MMCHMA | EMCHMA | aGBLMA | MNLMA | HAMA |
8 | 40 | - | - | - | 30 | 7 | 23 |
9 | - | - | 40 | - | 30 | 7 | 23 |
10 | - | 40 | - | - | 30 | 7 | 23 |
11 | - | - | - | 40 | 30 | 7 | 23 |
(表1中的MMCHMA、EMCHMA、MCHMA和ECHMA是通过使用实例1到4的合成程序来制备。aGBLMA(2-甲基-丙烯酸2-氧代-四氢-呋喃-3-基甲基丙烯酸酯)、HAMA(甲基丙烯酸3-羟基-金刚烷基酯)和MHLMA(2-氧代-2-(((1R,6S,8S)-5-氧代-4-氧杂三环[4.3.1.13,8]十一烷-2-基)氧基)乙基甲基丙烯酸酯)是可商购的。)
实例8:合成MCHMA/aGBLMA/X-GM-HL2/HAMA
使用3.65g的MCHMA、2.55g的aGBLMA、1.08g的MHLMA、2.72g的HAMA。通过使用通用聚合程序合成(目标聚合物。目标聚合物的总产率是76%(7.61g),具有8,600的Mw,1.57的PDI和131.4℃的玻璃转移温度。
实例9:合成MMCHMA/aGBLMA/X-GM-HL2/HAMA
使用2.81g的MMCHMA、1.69g的aGBLMA、0.71g的MHLMA、1.80g的HAMA。通过使用通用聚合程序合成目标聚合物。目标聚合物的总产率是51%(3.6g),具有11,800的Mw,1.45的PDI和125.4℃的玻璃转移温度。
实例10:合成ECHMA/aGBLMA/X-GM-HL2/HAMA
使用2.91g的EMCHMA、1.64g的aGBLMA、0.69g的MHLMA、1.75g的HAMA。通过使用通用聚合程序合成目标聚合物。目标聚合物的总产率是49%(3.4g),具有10,000的Mw,1.39的PDI和135.2℃的玻璃转移温度。
实例11:合成EMCHMA/aGBLMA/X-GM-HL2/HAMA
使用2.66g的ECHMA、1.74g的aGBLMA、0.74g的MNLMA、1.48g的HAMA。通过使用通用聚合程序合成目标聚合物。目标聚合物的总产率是58%(5.8g),具有9,900的Mw和1.47的PDI。
实例12-15:光致抗蚀剂组合物制备
用于PTD(正性显影)应用的光致抗蚀剂制备的通用程序
混合38.85g聚合物溶液(15%于PGMEA中)、31.04g的1-(4-(叔丁基)苯基)四氢-1H-噻吩-1-鎓2-(2-((1S,2R,4R)-双环[2.2.1]庚-2-基)-1,1,2,2-四氟乙氧基)-1,1,2,2-四氟乙烷-1-磺酸酯溶液(2%于甲基-2-羟基异丁酸酯中)、5.03g的(1,3-二羟基-2-(羟甲基)丙-2-基)氨基甲酸叔丁酯溶液(1%于甲基-2-羟基异丁酸酯中)、0.85g聚合物(GAM-DFPA/ECPMA)溶液(23.6%于PGMEA中)、17.64g的PGMEA和6.59g甲基-2-羟基异丁酸酯,并且用尼龙过滤器过滤。
实例11:通过掺合实例8中所制备的聚合物来制备光致抗蚀剂1
通过使用实例8中所制备的聚合物,使用光致抗蚀剂制备的通用程序,来制备光致抗蚀剂1。
实例12:通过掺合实例9中所制备的聚合物来制备光致抗蚀剂2
通过使用实例9中所制备的聚合物,使用光致抗蚀剂制备的通用程序,来制备光致抗蚀剂2。
实例13:通过掺合实例10中所制备的聚合物来制备光致抗蚀剂3
通过使用实例10中所制备的聚合物,使用光致抗蚀剂制备的通用程序,来制备光致抗蚀剂3。
实例14:通过掺合实例11中所制备的聚合物来制备光致抗蚀剂4
通过使用实例11中所制备的聚合物,使用光致抗蚀剂制备的通用程序,来制备光致抗蚀剂4。
实例15:光刻加工和性能
针对浸没式光刻测试,用具有300mm硅晶片的Lithius Track(TEL,TokyoElectron Co.)执行抗蚀剂和下伏抗反射涂层(BARC)和烘烤。用Nikon S610C浸没式193nm扫描仪进行曝光。通过使用Lithius,在2.38%氢氧化四甲基铵(TMAH)中使曝光的晶片显影。
光刻加工条件阐述于下表5中。衬底条件是具有最小反射性的双BARC(具有的BARC B,其在具有的BARC A上)。在100℃的软烘烤温度(SB)下光致抗蚀剂抗蚀剂膜厚度是曝光后烘烤(PEB)是100℃。照明条件是0.93NA,和具有0.8外和0.51内σ的环圈。相移掩模(PSM)用于以下的掩模图案的情况:对于致密线是72.5nm线和160nm间距,对于隔离线是110nm线和700nm间距,并且对于隔离沟槽是100nm空间和700nm间距。目标CD对于致密线是80nm线,并且对于隔离线是90nm线,并且对于隔离沟槽是90nm空间。
表5.光刻工艺条件
新型醚离去基的光刻性能
在表5中针对光刻性能,比较MMCHMA与MCHMA,并且还比较EMCHMA与ECHMA。与MCHMA相比,作为更具极性的离去基的MMCHMA在致密线和隔离沟槽图案下显示更倾斜的轮廓。当与ECHMA相比较时,EMCHMA也显示出类似的趋势。看起来这种倾斜轮廓影响EL和DoF界限以及LWR。与对照(MCPMA和ECHMA)相比,醚离去基(MMCHMA和EMCHMA)显示更差的EL和DoF界限以及LWR。由于因更具亲水特性和更低Tg所致,预期醚离去基比对照溶解地更快,因此其光速度(Eop:最优能量)比对照更快。令人关注的要点是与对照相比,极性离去基在隔离线下具有快得多的Eop。其意味着隔离线与致密线之间的Eop偏移更小。似乎与在致密线和隔离沟槽下相比,在具有相对丰富的酸浓度的隔离线下,具有极性离去基的聚合物更容易被去阻断并且在TMAH溶液中显影,并且其生成更小的隔离线CD。
实例16:制备用于NTD应用的光致抗蚀剂5
混合17.44g聚合物(IPAMA/IPCPMA/aGBLMA/X-GM-HL-2)溶液(15%于PGMEA中)、38.75g三苯基锍4-(((3r,5r,7r)-金刚烷-1-羰基)氧基)-1,1,2,2-四氟丁烷-1-磺酸盐(全称)溶液(1%于甲基-2-羟基异丁酸酯中)、4.58g的(4-(叔丁基)苯基)二苯基锍((3s,5s,7s)-金刚烷-1-基)氨基磺酸盐(全称)溶液(2%于甲基-2-羟基异丁酸酯中)、1.99g三辛胺(全称)溶液(1%于PGMEA中)、1.24g的2,2,4,4-四甲基戊二酸1-丁基5-异丁酯聚合物(5%于PGMEA中)、20.78g的PGMEA、9.69g的γ-丁内酯和5.52g的甲基-2-羟基异丁酸酯,并且用尼龙过滤器过滤。
实例17.-制备用于NTD应用的光致抗蚀剂6
混合17.44g聚合物(MMCHMA/IPAMA/IPCPMA/aGBLMA/X-GM-HL-2)溶液(15%于PGMEA中)、38.75g三苯基锍4-(((3r,5r,7r)-金刚烷-1-羰基)氧基)-1,1,2,2-四氟丁烷-1-磺酸盐溶液(1%于甲基-2-羟基异丁酸酯中)、4.58g的(4-(叔丁基)苯基)二苯基锍((3s,5s,7s)-金刚烷-1-基)氨基磺酸盐溶液(2%于甲基-2-羟基异丁酸酯中)、1.99g三辛胺溶液(1%于PGMEA中)、1.24g的2,2,4,4-四甲基戊二酸1-丁基5-异丁酯聚合物溶液(5%于PGMEA中)、20.78g的PGMEA、9.69g的γ-丁内酯和5.52g的甲基-2-羟基异丁酸酯,并且用尼龙过滤器过滤。
实例18.用于NTD应用的光刻性能
在TEL CLEAN TRAC LITHIUS i+上,300mm经HMDS底涂的硅晶片用ARTM26N(Rohmand Haas Electronic Materials)旋涂以形成第一底部抗反射涂层(BARC),随后在205℃下进行60秒烘烤过程,得到的第一BARC层厚度。
接着使用如下照射条件,通过Nikon S306C ArF浸没式扫描仪上的掩模曝光所制成的膜:1.3NA,具有XY极化的环圈,δ0.64-0.8。曝光剂量从23.0mJ/cm2以1mJ/cm2变化到47.0mJ/cm2。接着将曝光膜在90℃下曝光后烘烤60秒,随后使用TEL CLEAN TRAC LITHIUSi+,用乙酸正丁酯显影18秒,得到具有负性显影的图案。在Hitachi CG4000CD SEM上测量44nm 126间距沟槽、相移180°之亮场与透射率0.06之图案之临界尺寸(CD)。
Claims (15)
1.一种聚合物,包含有包含以下的重复单元:
碳脂环或杂脂环基,所述基团包含1)一个或多个酸不稳定环取代基和2)一个或多个任选被取代的醚或任选被取代的硫醚环取代基。
2.根据权利要求1所述的聚合物,其中所述重复单元包含碳脂环基。
3.根据权利要求1所述的聚合物,其中所述重复单元包含杂脂环基。
4.根据权利要求1或2所述的聚合物,其中1)所述酸不稳定环取代基是酯基,并且2)所述碳脂环或杂脂环基的碳环原子是所述酸不稳定酯基的季碳。
5.根据权利要求1到3中任一项所述的聚合物,其中所述碳脂环或杂脂环基包含一个或多个任选被取代的烷氧基环取代基。
6.根据权利要求1到5中任一项所述的聚合物,包含下式(I)或(I′)的结构:
其中在式(I)和(I′)中的每一个中:
X和Y独立地是C、O或S并且形成碳脂环族环或杂脂环族环;
R是非氢取代基;
R1是任选被取代的醚或任选被取代的硫醚;
R2是非氢取代基;
m是0或更大的整数整数;
n是正整数;并且m和n的总和不超过所述碳脂环族环或杂脂环族环的可用价。
7.根据权利要求1到6中任一项所述的聚合物,包含下式(II)的结构:
其中在式(II)中:
R是非氢取代基;
R1是任选被取代的醚或任选被取代的硫醚;
R2是非氢取代基;
m是0(其中不存在R2基团)或更大的整数整数;
n是正整数;并且m和n的总和不超过所述碳脂环族环或杂脂环族环的可用价。
8.根据权利要求1到7中任一项所述的聚合物,其中所述重复单元是聚合丙烯酸酯化合物。
9.一种光致抗蚀剂组合物,包含光敏性组分和根据权利要求1到8中任一项所述的聚合物。
10.根据权利要求9所述的光致抗蚀剂组合物,进一步包含第二不同聚合物。
11.一种加工光致抗蚀剂组合物的方法,包含:
在衬底上涂覆根据权利要求9或10所述的光致抗蚀剂组合物的层;
使所述光致抗蚀剂组合物层曝光于活化辐射;和
使所述曝光的光致抗蚀剂组合物显影,从而得到光致抗蚀剂浮雕图像。
12.根据权利要求11所述的方法,其中所述光致抗蚀剂组合物层被浸没式曝光。
13.一种单体,包含下式(I)或(I′)的结构:
其中在式(I)和(I′)中的每一个中:
X和Y独立地是C、O或S并且形成碳脂环族环或杂脂环族环;
R是非氢取代基;
R1是任选被取代的醚或任选被取代的硫醚;
R2是非氢取代基;
m是0或更大的整数整数;
n是正整数;并且m和n的总和不超过所述碳脂环族环或杂脂环族环的可用价。
14.一种单体,包含下式(II)的结构:
其中在式(II)中:
R是非氢取代基;
R1是任选被取代的醚或任选被取代的硫醚;
R2是非氢取代基;
m是0(其中不存在R2基团)或更大的整数整数;
n是正整数;并且m和n的总和不超过所述碳脂环族环或杂脂环族环的可用价。
15.根据权利要求13或14所述的单体,其中所述单体是丙烯酸酯化合物。
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US11487203B2 (en) | 2022-11-01 |
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