CN107337776B - 聚合物、有机层组成物以及形成图案的方法 - Google Patents
聚合物、有机层组成物以及形成图案的方法 Download PDFInfo
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- CN107337776B CN107337776B CN201610899626.XA CN201610899626A CN107337776B CN 107337776 B CN107337776 B CN 107337776B CN 201610899626 A CN201610899626 A CN 201610899626A CN 107337776 B CN107337776 B CN 107337776B
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Classifications
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- 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
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
- H01L21/308—Chemical or electrical treatment, e.g. electrolytic etching using masks
- H01L21/3081—Chemical or electrical treatment, e.g. electrolytic etching using masks characterised by their composition, e.g. multilayer masks, materials
-
- 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
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
-
- 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
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
-
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Abstract
本发明提供一种聚合物、有机层组成物以及形成图案的方法,包含由化学式1表示的结构单元的聚合物,和包含所述聚合物的有机层组成物,以及形成图案的方法。本发明提供的聚合物具有极好的抗蚀刻性同时具有良好溶解度特征。化学式1与具体实施方式中所定义的相同。
Description
相关申请的交叉引用
本申请主张2015年10月19日在韩国知识产权局提交的韩国专利申请第10-2015-0145367号的优先权和权益,其全部内容以引用的方式并入本文中。
技术领域
本发明涉及一种新颖聚合物、包含所述聚合物的有机层组成物以及使用所述有机层组成物形成图案的方法。尤其涉及一种聚合物、有机层组成物以及形成图案的方法。
背景技术
最近,根据电子装置的尺寸下调(小型化)和复杂性的高度集成设计已加快更高级材料和其相关工艺的发展,并且因此,使用常规的光刻胶的光刻法也需要新的图案化材料和技术。
在图案化工艺中,称为硬掩模层的有机层可形成为硬夹层以将光刻胶的精细图案转移到衬底上的足够深度处而不导致所述图案崩塌。
硬掩模层具有通过选择性蚀刻工艺来将光刻胶的精细图案转移到材料层的间层的作用。因此,硬掩模层需要如抗蚀刻性等的特征以经受多蚀刻工艺。
另一方面,最近已建议使用旋涂法而非化学气相沉积(CVD)法形成硬掩模层。一般来说,因为耐热性和抗蚀刻性与旋涂特征具有折衷(trade-off)关系,所以需要满足所有特征的有机层材料。
发明内容
一个实施例提供一种具有极好的抗蚀刻性并且同时具有良好溶解度特征的聚合物。
另一个实施例提供一种包含所述聚合物的有机层组成物。
又一个实施例提供一种使用有机层组成物形成图案的方法。
根据一个实施例,提供一种包含由化学式1表示的结构单元的聚合物。
[化学式1]
在化学式1中,
A为衍生自族群1中的一个化合物的经取代或未经取代的二价环基,
B为二价有机基团,以及
*为连接点。
[族群1]
在族群1中,
R0和R1独立地为氢、羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合。
在族群1中,R1可为经取代或未经取代的苯基。
在化学式1中,B可为经取代或未经取代的C1到C20亚烷基、经取代或未经取代的C3到C20亚环烷基、经取代或未经取代的C6到C20亚芳基、经取代或未经取代的C2到C20亚杂芳基、经取代或未经取代的C2到C20亚烯基、经取代或未经取代的C2到C20亚炔基或其组合。
由化学式1表示结构单元可由化学式1-1和化学式1-2中的一者表示。
[化学式1-1]
[化学式1-2]
在化学式1-1和化学式1-2中,
Z1为NR10、氧(O)或硫(S),Z2为氮(N),
R10、R11以及R12独立地为氢、羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合,
R13到R15独立地为羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合,
a和b独立地为介于0到3范围内的整数,
c为0或1,且
*为连接点。
聚合物可更包含由化学式2表示的结构单元。
[化学式2]
在化学式2中,
C为包含经取代或未经取代的芳环的基团,
D为二价有机基团,以及
*为连接点。
在化学式2中,C可为衍生自族群2中的一个化合物的经取代或未经取代的二价环基。
[族群2]
在族群2中,
Q1和Q2独立地为单键、经取代或未经取代的C1到C20亚烷基、经取代或未经取代的C3到C20亚环烷基、经取代或未经取代的C6到C20亚芳基、经取代或未经取代的C2到C20亚杂芳基、经取代或未经取代的C2到C20亚烯基、经取代或未经取代的C2到C20亚炔基、C=O、NRa、氧(O)、硫(S)或其组合,
Q3为氮(N)、CRb或其组合,且
Ra和Rb独立地为氢、经取代或未经取代的C1到C10烷基、卤素原子、含卤素的基团或其组合。
在化学式2中,D可为经取代或未经取代的C1到C20亚烷基、经取代或未经取代的C3到C20亚环烷基、经取代或未经取代的C6到C20亚芳基、经取代或未经取代的C2到C20亚杂芳基、经取代或未经取代的C2到C20亚烯基、经取代或未经取代的C2到C20亚炔基或其组合。
由化学式2表示的结构单元可由化学式2-1到化学式2-3中的一者表示。
[化学式2-1]
[化学式2-2]
[化学式2-3]
在化学式2-1到化学式2-3中,
R21和R22独立地为氢、羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合,
R23到R26独立地为羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合,
e到h独立地为介于0到2范围内的整数,且
*为连接点。
聚合物的重量平均分子量可为约500到约200,000。
根据另一个实施例,提供一种包含所述聚合物和溶剂的有机层组成物。
根据又一个实施例,一种形成图案的方法包含:在衬底上提供材料层,在材料层上涂覆有机层组成物,热处理有机层组成物以形成硬掩模层,在硬掩模层上形成含硅薄层,在含硅薄层上形成光刻胶层,使光刻胶层曝光并且显影以形成光刻胶图案,使用光刻胶图案选择性地去除含硅薄层和硬掩模层以使材料层的一部分暴露,以及蚀刻材料层的暴露部分。有机层组成物可使用旋涂法涂覆。
本发明提供的新颖聚合物具有令人满意的溶解度特征以及极好的机械特征、抗蚀刻性以及抗热性且适用于旋涂法中。
附图说明
图1为解释计算逸气量的计算方程式1的参考附图;
图2为解释评估平坦化特征的计算方程式3的参考附图。
具体实施方式
本发明的示例性实施例将在下文中进行详细描述,并且可以容易地由具有相关领域中普通技术人员执行。然而,本发明可按多种不同形式实施,并且不理解为限于本文中所阐述的示例性实施例。
如本文所使用,当未另外提供定义时,术语‘取代’可指由选自以下的取代基代替化合物的氢而经取代者:卤素原子(F、Br、Cl或I)、羟基、烷氧基、硝基、氰基、氨基、叠氮基、甲脒基、肼基、亚肼基、羰基、氨甲酰基、硫醇基、酯基、羧基或其盐、磺酸基或其盐、磷酸基或其盐、C1到C20烷基、C2到C20烯基、C2到C20炔基、C6到C30芳基、C7到C30芳烷基、C1到C30烷氧基、C1到C20杂烷基、C2到C20杂芳基、C3到C20杂芳烷基、C3到C30环烷基、C3到C15环烯基、C6到C15环炔基、C2到C30杂环烷基以及其组合。
如本文所用,当未另外提供定义时,术语‘杂’是指包含1个到3个由以下各者中选出的杂原子:N、O、S以及P。
下文中,描述根据一个实施例的聚合物。
根据一个实施例的聚合物包含由化学式1表示的结构单元。
[化学式1]
在化学式1中,
A为包含至少一个杂原子的烃环基且由族群1中选出,B为二价有机基团,以及*为连接点。
[族群1]
在族群1中,
R0和R1独立地为氢、羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合。
由化学式1表示的结构单元中由族群1中选出的环基的连接点不受特定限制。另外,由族群1中选出的环基中的氢可经取代基置换,且在本文中,取代基的类别和数目不受特定限制。
聚合物包含在由化学式1表示的结构单元中包含杂原子的烃环基。
聚合物在结构单元中包含杂原子,如氮、氧或硫,因此不仅可确保抗蚀刻性,而且基于极性通过杂原子增加而提高溶解度。另外,聚合物在结构单元中包含烃环基,因此由使用聚合物形成的有机层可确保极好的膜密度。
举例来说,在化学式1中,当A为时,R1可为经取代或未经取代的芳环基,例如经取代或未经取代的苯基。
在化学式1中,由B表示的二价有机基团可例如为经取代或未经取代的C1到C20亚烷基、经取代或未经取代的C3到C20亚环烷基、经取代或未经取代的C6到C20亚芳基、经取代或未经取代的C2到C20亚杂芳基、经取代或未经取代的C2到C20亚烯基、经取代或未经取代的C2到C20亚炔基或其组合的键联基团。
举例来说,在化学式1中,B可为未经取代的C1到C20亚烷基,或C1到C20亚烷基,其中至少一个氢经羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合置换,但不限于此。
举例来说,由化学式1表示的结构单元可由化学式1-1和化学式1-2中的一者表示,但不限于此。
[化学式1-1]
[化学式1-2]
在化学式1-1和化学式1-2中,
Z1为NR10、氧(O)或硫(S),Z2为氮(N),
R10、R11以及R12独立地为氢、羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合,
R13到R15独立地为羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合,
a和b独立地为介于0到3范围内的整数,
c为0或1,且
*为连接点。
聚合物可还包含由化学式2表示的结构单元。
[化学式2]
在化学式2中,
C为包含经取代或未经取代的芳环的基团,
D为二价有机基团,以及
*为连接点。
举例来说,在化学式2中,C可为衍生自族群2中的一个化合物的经取代或未经取代的二价环基。
[族群2]
在族群2中,
Q1和Q2独立地为单键、经取代或未经取代的C1到C20亚烷基、经取代或未经取代的C3到C20亚环烷基、经取代或未经取代的C6到C20亚芳基、经取代或未经取代的C2到C20亚杂芳基、经取代或未经取代的C2到C20亚烯基、经取代或未经取代的C2到C20亚炔基、C=O、NRa、氧(O)、硫(S)或其组合,
Q3为氮(N)、CRb或其组合,且
Ra和Rb独立地为氢、经取代或未经取代的C1到C10烷基、卤素原子、含卤素的基团或其组合。
举例来说,在化学式2中,D可为以下的键联基团:经取代或未经取代的C1到C20亚烷基、经取代或未经取代的C3到C20亚环烷基、经取代或未经取代的C6到C20亚芳基、经取代或未经取代的C2到C20亚杂芳基、经取代或未经取代的C2到C20亚烯基、经取代或未经取代的C2到C20亚炔基或其组合。
举例来说,在化学式2中,D可为未经取代的C1到C20亚烷基或C1到C20亚烷基,其中至少一个氢经羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合置换,但不限于此。
举例来说,由化学式2表示的结构单元可由化学式2-1到化学式2-3中的一者表示,但不限于此。
[化学式2-1]
[化学式2-2]
[化学式2-3]
在化学式2-1到化学式2-3中,
R21和R22独立地为氢、羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合,
R23到R26独立地为羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合,
e到h独立地为介于0到2范围内的整数,且
*为连接点。
聚合物可还包含由化学式2表示的结构单元,且进而聚合物可具有改进的抗蚀刻性。
举例来说,聚合物可通过使用作为亲核试剂的杂芳环结构和作为亲电子试剂的多芳环结构单体的缩合聚合来制备。举例来说,包含于由化学式1表示的结构单元中的如氮、氧或硫的杂原子可在形成聚合物之后起阻燃剂的作用,因此改进聚合物的抗蚀刻性以及在缩合聚合期间起还原剂的作用。
举例来说,聚合物的重量平均分子量可为约500到约200,000。当聚合物的重量平均分子量在所述范围内时,包含所述聚合物的有机层组成物(例如硬掩模组成物)可通过调节碳的量和溶剂中的溶解度而最优化。
当聚合物用作有机层材料时,可不仅在下部衬底(或膜)中存在梯级时或形成图案时提供极好的间隙填充和平坦化特征,而且还可在于烘烤期间不形成针孔和空隙或不使厚度分布劣化的情况下形成均一薄膜。
根据另一个实施例,提供一种包含所述聚合物和溶剂的有机层组成物。
溶剂可为足以溶解或分散聚合物的任何溶剂,并且可为例如由以下各者中选出的至少一者:丙二醇、二乙酸丙二醇酯、甲氧基丙二醇、二甘醇、二甘醇丁基醚、三(乙二醇)单甲基醚、丙二醇单甲基醚、丙二醇单甲基醚乙酸酯、环己酮、乳酸乙酯、γ-丁内酯、甲基吡咯烷酮、乙酰丙酮以及3-乙氧基丙酸乙酯。
聚合物可按有机层组成物的总量计约1重量%到50重量%的量包含在内。当聚合物以所述范围被包含时,可控制有机层的厚度、表面粗糙度以及平坦化。
有机层组成物可还包含表面活性剂、交联剂、热酸产生剂、塑化剂等添加剂。
表面活性剂可包含例如烷基苯磺酸盐、烷基吡啶鎓盐、聚乙二醇或季铵盐,但并不限于此。
交联剂可例如为三聚氰胺类试剂、经取代的脲类试剂或聚合物类试剂。在一个实施例中,具有至少两个交联形成取代基的交联剂可例如为如甲氧基甲基化甘脲、丁氧基甲基化甘脲、甲氧基甲基化三聚氰胺、丁氧基甲基化三聚氰胺、甲氧基甲基化苯并胍胺、丁氧基甲基化苯并胍胺、甲氧基甲基化脲、丁氧基甲基化脲、甲氧基甲基化硫脲或丁氧基甲基化硫脲等的化合物。
交联剂可以是具有较高耐热性的交联剂。具有较高耐热性的交联剂可以是在分子中包括含芳族环(例如苯环或萘环)的交联取代基的化合物。
热酸产生剂可以是例如酸性化合物,如对甲苯磺酸、三氟甲磺酸、对甲苯磺酸吡啶鎓、水杨酸、磺基水杨酸、柠檬酸、苯甲酸、羟基苯甲酸、萘碳酸等或/和2,4,4,6-四溴环己二烯酮、安息香甲苯磺酸酯、2-硝基苯甲基甲苯磺酸酯、其它有机磺酸烷基酯等,但不限于此。
以100重量份的有机层组成物计,添加剂可以约0.001重量份到40重量份的量存在。当添加剂以所述范围被包含时,可在不改变有机层组成物光学特性的情况下改进溶解度。
根据另一个实施例,提供使用有机层组成物制造的有机层。有机层可例如由在衬底上涂布有机层组成物并且对其进行热处理以固化来形成,并且可包含例如硬掩模层、平坦化层、牺牲层、填充物等以用于电子装置。
下文描述一种通过使用有机层组成物形成图案的方法。
根据一个实施例,形成图案的方法包含:在衬底上提供材料层,涂覆包含聚合物和溶剂的有机层组成物,热处理包含单体和溶剂的有机层组成物以形成硬掩模层,在硬掩模层上形成含硅薄层,在含硅薄层上形成光刻胶层,使光刻胶层曝光并且显影以形成光刻胶图案,使用光刻胶图案选择性地去除含硅薄层和硬掩模层以使材料层的一部分暴露,以及蚀刻材料层的暴露部分。
衬底可以是例如硅芯片、玻璃衬底或聚合物衬底。
材料层为最终将图案化的材料,例如,金属层,如铝层和铜层;半导体层,如硅层;或绝缘层,如氧化硅层和氮化硅层。材料层可通过如化学气相沉积(chemical vapordeposition;CVD)工艺的方法来形成。
有机层组成物与上文所述的相同,并且可按溶液形式通过旋涂法来涂覆。本文中,有机层组成物的厚度不受特别限制,但可以是例如约50埃到约100,000埃。
可在例如约100℃到约500℃下进行有机层组成物的热处理约10秒到约1小时。
含硅薄层可由例如SiCN、SiOC、SiON、SiOCN、SiC、SiO和/或SiN形成。
所述方法可还包含在于含硅薄层上形成光刻胶层之前形成底部抗反射涂层(BARC)。
光刻胶层的曝光可使用例如ArF、KrF或EUV进行。在曝光之后,热处理可在约100℃到约500℃下进行。
可经由使用蚀刻气体的干式蚀刻工艺对材料层的暴露部分实施蚀刻工艺,且蚀刻气体可为例如(但不限于)CHF3、CF4、Cl2、BCl3以及其混合气体。
经蚀刻的材料层可以多个图案形成,并且多个图案可以是金属图案、半导体图案、绝缘图案以及其类似图案,例如半导体集成电路装置的不同图案。
在下文中,参考实例对本发明进行更详细地说明。然而,这些实例是示例性的,并且本发明并不限于此。
合成实例
合成实例1
将吲哚(3.5克,30摩尔)、芘(6克,30摩尔)以及多聚甲醛(1.8克,20摩尔)放入250毫升烧瓶中。随后,将通过溶解对甲苯磺酸单水合物(0.57克,3毫摩尔)于100克丙二醇单甲基醚乙酸酯(propylene glycol monomethyl ether acetate,PGMEA)中获得的溶液放入烧瓶中,且在90℃下搅拌混合物。接着,每小时从聚合反应物获取样品,且当样品具有3,000到3,500的重量平均分子量时,反应完成。
当反应完成时,将反应物冷却到室温并且添加到300克蒸馏水和300克甲醇中,并将混合物剧烈搅拌并使其静置。在自其去除上清液之后,其中的沉淀溶解于100克丙二醇单甲基醚乙酸酯(PGMEA)中,且溶液与300克甲醇和300克蒸馏水一起剧烈搅拌并使其静置(第一工艺)。在再次自其去除获得的上清液之后,其中的沉淀溶解于80克丙二醇单甲基醚乙酸酯(PGMEA)中(第二工艺)。第一工艺和第二工艺被视为一个纯化工艺,并且这一纯化工艺重复三次。
使纯化聚合物溶解于80克丙二醇单甲基醚乙酸酯(PGMEA)中,并且在减压下去除残存于溶液中的甲醇和蒸馏水,获得包含由化学式1a表示的结构单元的聚合物。
[化学式1a]
(重量平均分子量:2,800和多分散性:1.51)
合成实例2
根据与合成实例1相同的方法制备由化学式1b表示的聚合物,不同之处在于使用羟基芘代替合成实例1中的芘。
【化学式1b]
(重量平均分子量:3,150和多分散性:1.59)
合成实例3
根据与合成实例1相同的方法制备包含由化学式1c表示的结构单元的聚合物,不同之处在于使用1-萘酚代替合成实例1中的芘。
[化学式1c]
(重量平均分子量:1,890和多分散性:1.45)
合成实例4
根据与合成实例1相同的方法制备包含由化学式1d表示的结构单元的聚合物,不同之处在于使用2-苯基苯并恶唑代替吲哚且使用1-萘酚代替合成实例1中的芘。
[化学式1d]
(重量平均分子量:2,630和多分散性:1.70)
合成实例5
根据与合成实例1相同的方法制备包含由化学式1e表示的结构单元的聚合物,不同之处在于使用2-苯基苯并恶唑代替吲哚且使用羟基芘代替合成实例1中的芘。
[化学式1e]
(重量平均分子量:3,080和多分散性:1.41)
合成实例6
根据与合成实例1相同的方法制备包含由化学式1f表示的结构单元的聚合物,不同之处在于使用2-苯基苯并恶唑代替吲哚且使用1-萘酚代替合成实例1中的芘。
[化学式1f]
(重量平均分子量:3,650和多分散性:1.38)
合成实例7
根据与合成实例1相同的方法制备包含由化学式1g表示的结构单元的聚合物,不同之处在于使用2-苯基苯并恶唑代替吲哚且使用羟基芘代替合成实例1中的芘。
[化学式1g]
(重量平均分子量:3,810和多分散性:1.72)
合成实例8
根据与合成实例1相同的方法制备包含由化学式1h表示的结构单元的聚合物,不同之处在于使用4,4′-(9H-芴-9,9-二基)二酚代替合成实例1中的芘。
[化学式1h]
(重量平均分子量:3,900和多分散性:1.69)
合成比较例1
将9,9-双(4-羟基苯基)-9H-芴(21克,0.057摩尔)和4,4-甲氧基甲苯(9.6克,0.057摩尔)依序放入500毫升烧瓶中且溶解于51克丙二醇单甲基醚乙酸酯(PGMEA)中,将对甲苯磺酸单水合物(0.001摩尔)添加到其中,且在100℃下搅拌混合物5小时。接着,每小时从聚合反应物获取样品,且当样品具有3,500到4,000的重量平均分子量时,反应完成。接着,通过与合成实例1相同的纯化工艺获得包含由化学式A表示的结构单元的聚合物。
[化学式A]
合成比较例2
将9,9-双(4-羟基苯基)-9H-芴(35克,0.1摩尔)、1-萘酚(14.4克,0.1摩尔)以及三聚甲醛(1.2克,0.034摩尔)放入500毫升烧瓶中。随后,将通过溶解对甲苯磺酸单水合物(0.19克,0.34摩尔)于162克丙二醇单甲基醚乙酸酯(PGMEA)中获得的溶液添加到烧瓶中。在100℃下搅拌混合物5小时。接着,每小时从聚合反应物获取样品,且当样品具有3,500到4,000的重量平均分子量时,反应完成。接着,通过与合成比较例1相同的纯化工艺获得包含由化学式B表示的结构单元的聚合物。
[化学式B]
制备硬掩模组成物
实例1
根据合成实例1的聚合物溶解于丙二醇单甲基醚乙酸酯(PGMEA)和乳酸乙酯(EL)(7∶3(v/v))的混合溶剂中,且用0.1μm铁氟龙(TEFLON)(四氟乙烯〕过滤器过滤溶液,制备硬掩模组成物。取决于所要厚度,在关于按硬掩模组成物的总重量计3.0重量%到15.0重量%范围内的重量调节聚合物。
实例2到实例8
根据实例2到实例8的每一硬掩模组成物根据与实例1相同的方法制备,不同之处在于分别使用根据合成实例2到合成实例8的聚合物代替根据合成实例1的化合物。
比较例1和比较例2
每一硬掩模组成物根据与实例1相同的方法制备,不同之处在于分别使用根据合成比较例1和合成比较例2的聚合物代替根据合成实例1的聚合物。
评估1:膜密度
根据实例1到实例8和比较例1和比较例2的每一硬掩模组成物旋涂于硅芯片上,在400℃下热处理2分钟,形成约1000埃厚的薄膜。通过使用由帕纳科(PANalytical)制造的X射线衍射设备测量薄膜的膜密度。
结果在表1中示出。
[表1]
膜密度(克/立方厘米) | |
实例1 | 1.35 |
实例2 | 1.36 |
实例3 | 1.31 |
实例4 | 1.30 |
实例5 | 1.31 |
实例6 | 1.29 |
实例7 | 1.29 |
实例8 | 1.29 |
比较例1 | 1.21 |
比较例2 | 1.23 |
参看表1,分别由根据实例1到实例8的硬掩模组成物形成的每一薄膜比分别由根据比较例1和比较例2的硬掩模组成物形成的每一薄膜显示更高膜密度。
换句话说,相比于根据比较例1和比较例2的硬掩模组成物,根据实例1到实例8的硬掩模组成物全部形成致密且坚实的薄膜。
评估2:逸气
根据实例1到实例8和比较例1和比较例2的硬掩模组成物分别在硅芯片上涂布为约2000埃厚且在400℃下烘烤5分钟,且通过使用石英晶体微天平(Quartz CrystalMicrobalance;QCM)测量在烘烤期间产生的逸气,且根据图1中的计算方程式1计算逸气的量(纳克)。
结果示出在表2中。
[表2]
逸气量(纳克) | |
实例1 | 76 |
实例2 | 67 |
实例3 | 92 |
实例4 | 76 |
实例5 | 72 |
实例6 | 69 |
实例7 | 68 |
实例8 | 65 |
比较例1 | 101 |
比较例2 | 98 |
参看表2,相比于分别由根据比较例1和比较例2的硬掩模组成物形成的每一薄膜,分别由根据实例1到实例8的硬掩模组成物形成的每一薄膜在烘烤期间在400℃的高温下产生相对较小量的逸气。因此,确认根据实例1到实例8的硬掩模组成物有利地应用于高温工艺。
评估3:抗蚀刻性
根据实例1到实例8和比较例1和比较例2的硬掩模组成物分别旋涂于硅芯片上且在400℃下在热板上烘烤2分钟,形成约4000埃厚的薄膜。通过使用K-MAC制造的薄膜厚度测量设备来测量薄膜的厚度。
随后,分别用CF4气体和N2/O2混合气体干式蚀刻薄膜60秒和100秒,且接着测量薄膜的厚度。
从如计算方程式2中所示的整体蚀刻速率(BER)评估薄膜的抗蚀刻性。
[计算方程式2]
整体蚀刻速率(BER)=(薄膜初始厚度-蚀刻后薄膜厚度)/蚀刻时间(埃/秒)
结果示于表3中。
[表3]
参看表3,分别由根据实例1到实例8的硬掩模组成物形成的每一薄膜比分别由根据比较例1和比较例2的硬掩模组成物形成的每一薄膜显示更低整体蚀刻速率。
因此,相比于根据比较例1和比较例2的硬掩模组成物,根据实例1到实例8的硬掩模组成物显示高抗蚀刻性。
评估4:间隙填充和平坦化特征
根据实例1到实例8和比较例1和比较例2的硬掩模组成物分别旋涂于图案化硅芯片上且在400℃下烘烤2分钟,且接着通过使用FE-SEM设备检查间隙填充特征和平坦化特征。
通过用电子扫描显微镜(SEM)检查图案的横截面以查看是否存在空隙来评估间隙填充特征,且通过从图案横截面的SEM图像测量硬掩模层的厚度且将其放入图2的计算方程式3中评估平坦化特征。本文中,平坦化特征极好,因为厚度h1与厚度h2之间的差异较小。
另一方面,通过调节包含于根据实例1到实例8和比较例1和比较例2的硬掩模组成物中的聚合物的量,烘烤之后的厚度h1为2000埃。
结果示于表4中。
[表4]
参看表4,根据实例1到实例8的硬掩模组成物显示相比于根据比较例1和比较例2的硬掩模组成物的极好平坦化,以及深图案深度(纵横比=1∶15)的条件下的无空隙,因此间隙填充特征极好。
虽然已经结合目前视为实用示例性实施例的内容来描述本发明,但应理解本发明不限于所公开的实施例,而是相反,本发明旨在涵盖包含在所附权利要求书的精神和范围内的各种修改和等效布置。
Claims (18)
1.一种聚合物,包括由化学式1表示的结构单元:
化学式1
其中,在化学式1中,
A为衍生自族群1中的一个化合物的经取代或未经取代的二价环基,
B为二价有机基团,以及
*为连接点,
族群1
其中,在族群1中,
R0和R1独立地为氢、羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合,
其中所述聚合物还包括由化学式2表示的结构单元:
化学式2
其中,在化学式2中,
C为包含经取代或未经取代的芳环的基团,
D为二价有机基团,以及
*为连接点。
2.根据权利要求1所述的聚合物,其中在族群1中,R1为经取代或未经取代的苯基。
3.根据权利要求1所述的聚合物,其中B为经取代或未经取代的C1到C20亚烷基、经取代或未经取代的C3到C20亚环烷基、经取代或未经取代的C6到C20亚芳基、经取代或未经取代的C2到C20亚杂芳基、经取代或未经取代的C2到C20亚烯基、经取代或未经取代的C2到C20亚炔基或其组合。
4.根据权利要求1所述的聚合物,其中由化学式1表示的结构单元由化学式1-1和化学式1-2中的一者表示:
化学式1-1
化学式1-2
其中,在化学式1-1和化学式1-2中,
Z1为NR10、氧或硫,Z2为氮,
R10、R11以及R12独立地为氢、羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合,
R13到R15独立地为羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合,
a和b独立地为介于0到3范围内的整数,
c为0或1,以及
*为连接点。
5.根据权利要求1所述的聚合物,其中C为衍生自族群2中的一个化合物的经取代或未经取代的二价环基:
族群2
其中,在族群2中,
Q1和Q2独立地为单键、经取代或未经取代的C1到C20亚烷基、经取代或未经取代的C3到C20亚环烷基、经取代或未经取代的C6到C20亚芳基、经取代或未经取代的C2到C20亚杂芳基、经取代或未经取代的C2到C20亚烯基、经取代或未经取代的C2到C20亚炔基、C=O、NRa、氧、硫或其组合,
Q3为氮、CRb或其组合,以及
Ra和Rb独立地为氢、经取代或未经取代的C1到C10烷基、卤素原子、含卤素的基团或其组合。
6.根据权利要求1所述的聚合物,其中D为经取代或未经取代的C1到C20亚烷基、经取代或未经取代的C3到C20亚环烷基、经取代或未经取代的C6到C20亚芳基、经取代或未经取代的C2到C20亚杂芳基、经取代或未经取代的C2到C20亚烯基、经取代或未经取代的C2到C20亚炔基或其组合。
7.根据权利要求1所述的聚合物,其中由化学式2表示的结构单元由化学式2-1到化学式2-3中的一者表示:
化学式2-1
化学式2-2
化学式2-3
其中,在化学式2-1到化学式2-3中,
R21和R22独立地为氢、羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合,
R23到R26独立地为羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合,
e到h独立地为介于0到2范围内的整数,以及
*为连接点。
8.根据权利要求1所述的聚合物,其中所述聚合物的重量平均分子量为500到200,000。
9.一种有机层组成物,包括包含由化学式1表示的结构单元的聚合物以及溶剂:
化学式1
其中,在化学式1中,
A为衍生自族群1中的一个化合物的经取代或未经取代的二价环基,
B为二价有机基团,以及
*为连接点,
族群1
其中,在族群1中,
R0和R1独立地为氢、羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合,
其中所述聚合物还包括由化学式2表示的结构单元:
化学式2
其中,在化学式2中,
C为包含经取代或未经取代的芳环的基团,
D为二价有机基团,以及
*为连接点。
10.根据权利要求9所述的有机层组成物,其中在族群1中,R1为经取代或未经取代的苯基。
11.根据权利要求9所述的有机层组成物,其中B为经取代或未经取代的C1到C20亚烷基、经取代或未经取代的C3到C20亚环烷基、经取代或未经取代的C6到C20亚芳基、经取代或未经取代的C2到C20亚杂芳基、经取代或未经取代的C2到C20亚烯基、经取代或未经取代的C2到C20亚炔基或其组合。
12.根据权利要求9所述的有机层组成物,其中由化学式1表示的结构单元由化学式1-1和化学式1-2中的一者表示:
化学式1-1
化学式1-2
其中,在化学式1-1和化学式1-2中,
Z1为NR10、氧或硫,Z2为氮,
R10、R11以及R12独立地为氢、羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合,
R13到R15独立地为羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合,
a和b独立地为介于0到3范围内的整数,
c为0或1,以及
*为连接点。
13.根据权利要求9所述的有机层组成物,其中C为衍生自族群2中的一个化合物的经取代或未经取代的二价环基:
族群2
其中,在族群2中,
Q1和Q2独立地为单键、经取代或未经取代的C1到C20亚烷基、经取代或未经取代的C3到C20亚环烷基、经取代或未经取代的C6到C20亚芳基、经取代或未经取代的C2到C20亚杂芳基、经取代或未经取代的C2到C20亚烯基、经取代或未经取代的C2到C20亚炔基、C=O、NRa、氧、硫或其组合,
Q3为氮、CRb或其组合,以及
Ra和Rb独立地为氢、经取代或未经取代的C1到C10烷基、卤素原子、含卤素的基团或其组合。
14.根据权利要求9所述的有机层组成物,其中D为经取代或未经取代的C1到C20亚烷基、经取代或未经取代的C3到C20亚环烷基、经取代或未经取代的C6到C20亚芳基、经取代或未经取代的C2到C20亚杂芳基、经取代或未经取代的C2到C20亚烯基、经取代或未经取代的C2到C20亚炔基或其组合。
15.根据权利要求9所述的有机层组成物,其中由化学式2表示的结构单元由化学式2-1到化学式2-3中的一者表示:
化学式2-1
化学式2-2
化学式2-3
其中,在化学式2-1到化学式2-3中,
R21和R22独立地为氢、羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合,
R23到R26独立地为羟基、甲氧基、乙氧基、卤素原子、含卤素的基团、经取代或未经取代的C1到C30烷基、经取代或未经取代的C6到C30芳基或其组合,
e到h独立地为介于0到2范围内的整数,以及
*为连接点。
16.根据权利要求9所述的有机层组成物,其中所述聚合物的重量平均分子量为500到200,000。
17.一种形成图案的方法,包括:
在衬底上提供材料层,
在所述材料层上涂覆根据权利要求9到16中任一项所述的有机层组成物,
热处理所述有机层组成物以提供硬掩模层,
在所述硬掩模层上提供含硅薄层,
在所述含硅薄层上提供光刻胶层,
使所述光刻胶层曝光并且显影以形成光刻胶图案,
使用所述光刻胶图案选择性地去除所述含硅薄层和所述硬掩模层以使所述材料层的一部分暴露,以及
蚀刻所述材料层的暴露部分。
18.根据权利要求17所述的形成图案的方法,其中所述有机层组成物使用旋涂法涂覆。
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JP6923301B2 (ja) | 2021-08-18 |
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