CN109988259B - 单体、聚合物和包含其的光刻组合物 - Google Patents
单体、聚合物和包含其的光刻组合物 Download PDFInfo
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- CN109988259B CN109988259B CN201811552540.5A CN201811552540A CN109988259B CN 109988259 B CN109988259 B CN 109988259B CN 201811552540 A CN201811552540 A CN 201811552540A CN 109988259 B CN109988259 B CN 109988259B
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Classifications
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- C07D345/00—Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms
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- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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Abstract
包含一个或多个Te原子的新单体和聚合物材料。在一个方面,提供可用于极紫外光刻的含碲单体和聚合物。
Description
技术领域
本发明涉及包含一个或多个Te原子的新单体和聚合物材料。在一个优选方面,提供含碲单体和聚合物,其可用于光致抗蚀剂和用于极紫外光刻的其它涂料组合物。
背景技术
极紫外光刻技术(“EUVL”)是将光学光刻技术替代特征尺寸<20nm的体积半导体制造的主要技术选择之一。极短的波长(13.4nm)是多代技术所需高分辨率的关键促进因素。另外,整个系统概念-扫描曝光、投影光学、掩模格式和抗蚀技术-与当前光学技术所使用的非常相似。像以前的光刻技术代一样,EUVL由抗蚀技术、曝光工具技术和掩膜技术组成。主要挑战是EUV源功率和吞吐量。EUV电源的任何改进都将直接影响目前严格的抗蚀剂灵敏度规格。事实上,EUVL成像中的一个主要问题是抗蚀剂灵敏度,灵敏度越低,需要的源功率越大或者需要完全曝光抗蚀剂的曝光时间越长。功率水平越低,噪音对印刷线的线边缘粗糙度(LER)的影响就越大。
已经进行各种尝试来改变EUV光致抗蚀剂组合物的构成,以改进功能特性的性能。除其它之外,已经报导多种聚合物化合物。参见US 20040241574和5989776。又见WO2017033943A1;WO2017188450;WO2017188451;Fukunaga等人。《光聚合物科学与技术杂志(J.Photo.Polym.Sci.Tech.)》,2017,30,103-107;Kudo等人,《化学快报(Chem.Letters)》,2011,40,762-764。
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。
期望有可以提供增强成像能力的新型光致抗蚀剂组合物,包括可用于EUVL的新型光致抗蚀剂组合物。
发明内容
我们现在提供包含一个或多个碲(Te)原子的新单体和聚合物。我们还提供包括光致抗蚀剂组合物和底层涂料组合物(例如抗反射或平面化组合物)的光刻组合物,其包含一种或多种本发明的单体或聚合物。
在一个优选方面,提供加成型聚合物,其包含一个或多个包含一个或多个Te原子的重复单元。在另一优选方面,提供包含一个或多个侧接于聚合物主链的部分的聚合物,其中一个或多个侧接部分包含一个或多个Te原子。在本发明的聚合物中,聚合物的一个或多个Te原子合适地为二价或四价。
在一优选方面,提供包含(a)一个或多个Te原子;(b)一个或多个不饱和可聚合基团,包括一个或多个烯系可聚合基团的单体。这类单体的一个或多个Te原子合适地为二价或四价。
优选的单体可进一步包含一个或多个酸可裂解基团、极性基团和/或碱反应性基团。
合适的酸可裂解基团包括酯和缩醛基团,其可在光刻处理期间与存在于光致抗蚀剂或其它组合物层的光产生酸反应。多种极性基团将是合适的,包括被一个或多个包含一个或多个杂原子的部分取代的烷基和芳基,例如氰基、羟基或环氧基。合适的碱反应性或酸性基团也可以不同,并且包括例如酸性或碱反应性基团,例如卤代羟基烷基,包括六氟醇(HFA)、羧酸、磺酸、磺酰胺、内酯或酚。
一个或多个可聚合基团合适地可以是烯系不饱和基团,例如任选被取代的丙烯酸酯、任选被取代的丙烯酰胺、任选被取代的乙烯基醚部分、任选被取代的非环状乙烯基或环烯烃部分。
更具体地说,在某些方面中,优选的单体可包括丙烯酸酯部分。优选的丙烯酸酯单体可包含对应于下式(I)的结构:
其中R是氢或被取代的非氢,例如任选被取代的C1-16烷基,包括任选被取代的甲基;并且
P包含一个或多个Te原子。
在某些优选方面,P可包含一个或多个酸可裂解基团、极性基团和/或碱反应性基团。
在某些方面,优选的丙烯酸酯单体包括包含碳或杂芳香族(碳环芳基或杂芳基)或脂环族(碳脂环族或杂脂环族)基团的单体,例如包含下式(IA)的结构的单体:
其中在式(IA)中,R和每个P与上式(I)中的定义相同;
S是连接基团,例如化学键或具有1到20个或更多个可任选被取代的碳和杂原子(N、O、S)的链,其包括在所描绘的酯键附近提供季碳原子;
每个R1是相同或不同的非氢取代基,并且可包含一个或多个酸可裂解基团、极性基团或碱反应性基团,或任选地可包含一个或多个烷基;
m是等于1到G允许的最大价数的整数,并且m通常是1、2、4、5、6、7或8的整数。
n是等于0(其中不存在R1基团)到G允许的最大价数的整数,并且m通常是0、1、2、3、4、5、6、7或8的整数;并且
在某些方面,优选的丙烯酸酯单体可包含一个或多个碳环芳基,例如苯基或萘基。这类优选的单体包括包含对应于下式(IB)的结构的单体:
其中在式(IB)中:
R与上述式(I)中的定义相同;
S是连接基团,例如化学键或具有1到20个或更多个可任选被取代的碳和杂原子(N、O、S)的链,其包括在所描绘的酯键附近提供季碳原子;
P包含一个或多个Te原子和任选地还可包含一个或多个酸可裂解基团、极性基团或碱反应性基团;并且
每个R1是相同或不同的非氢取代基,并且可包含一个或多个酸可裂解基团、极性基团或碱反应性基团,或任选地可包含一个或多个烷基;并且
n是0(其中不存在R1基团)到4的整数,m是1到4的整数。
在某些优选方面,P或至少一个R1基团任选地包含至少一个酸不稳定、极性或碱反应性基团。
在某些方面,优选的丙烯酸酯单体可包含一个或多个碳环芳基,其中Te原子直接被碳环芳环取代(Te和碳环芳环原子之间没有插入其它原子)。举例来说,优选的是包含下式(IC)的结构的单体:
其中在式(IC)中:
R和S各自与上式(IB)中定义的相同;
每个R1是相同或不同的非氢取代基,并且可包含一个或多个酸可裂解基团、极性基团和/或碱反应性基团;
R2是非氢取代基,并且任选地可包含一个或多个酸可裂解基团、极性基团和/或碱反应性基团;和
n是0(其中不存在R1基团)到4的整数。
在式(IC)的单体的某些优选实施例中,至少一个R1基团或一个R2基团包含至少一个酸不稳定、极性或碱反应性基团。
在某些其它方面,优选的单体可包含乙烯基醚部分。优选乙烯基醚单体可包含对应于下式(II)的结构:
其中在式(II)中,R和P与上式(I)中所定义的相同。
在某些方面,优选乙烯基醚单体包括包含碳或杂芳香族(碳环芳基或杂芳基)或脂环族(碳脂环族或杂脂环族)基团的单体,例如包含下式(IIA)的结构的单体:
其中在式(IIA)中,R、每个P、S、每个R1、m和n与上式(IA)定义的相同;并且
优选乙烯基醚单体可包含一个或多个碳环芳基,例如苯基或萘基。这类优选的单体包括包含对应于下式(IIB)的结构的单体:
其中在式(IIB)中,R、S、P、R1和n与上式(IB)中所定义的相同。
包含一个或多个碳环芳基的优选乙烯基醚单体包括其中Te原子直接被碳环芳环取代的基团。举例来说,优选的是包含下式(IIC)的结构的单体:
其中在式(IIC)中,R、S、R1、R2和n与上式(IC)中所定义的相同。
在某些其它方面,优选的单体可包含乙烯基部分并且适当地可包含对应于下式(III)的结构:
其中在式(III)中,R和P与上式(I)中所定义的相同。
在某些方面中,优选乙烯基单体包括包含碳或杂芳香族(碳环芳基或杂芳基)或脂环族(碳脂环族或杂脂环族)基团的单体,例如包含下式(IIIA)的结构的单体:
其中在式(IIIA)中,R、每个P、S、每个R1、m和n与上式(IA)中所定义的相同;并且
在某些方面,优选乙烯基单体可包含一个或多个碳环芳基,例如苯基或萘基。这类优选的单体包括包含对应于下式(IIIB)的结构的单体:
其中在式(IIIA)中,R、P、R1和n与上式(IB)中所定义的相同。
包含一个或多个碳环芳基的优选乙烯基单体包括其中Te原子直接被碳环芳环取代的基团。举例来说,优选的是包含下式(IIIC)的结构的单体:
其中在式(IIIC)中,R、S、R1、R2和n与上式(IC)中所定义的相同。
在一其它优选实施例中,提供包含一个或多个Te原子的环烯烃单体。如本文所提及,环烯烃是具有至少一个内环碳-碳单内环复键的非芳香族环结构(例如5到约20个环原子,在某些实施例中优选具有5或6个环原子)。在某些方面,优选的环烯烃单体包括具有下式(IV)的结构的单体:
其中在式(IV)中:
P包含一个或多个Te原子;
每个R1是相同或不同的非氢取代基,并且可包含一个或多个酸可裂解基团、极性基团或碱反应性基团,或任选地可包含一个或多个烷基;并且
n是等于0(其中不存在R1基团)到脂环族环允许的最大价数的整数,并且n通常是0、1、2、3、4或5。在上式(IV)中,所描绘的环结构可以是多种结构,包括在单一、稠合或连接的环结构中具有5到约20个环原子,并且在某些实施例中,5或6个环原子可以是优选的。尽管一个或多个芳香族环可以与脂环族(非芳香族)环共价连接(包括稠合),但含有式(IV)中所描绘的碳-碳双键的环是非芳香族的。
在又一其它优选方面,提供包含一个或多个Te原子和一个或多个内酯官能团的单体。举例来说,在上式(I)、(IA)、(IB)、(IC)、(II)、(IIA)、(IIB)、(IIC)、(III)、(IIIA)、(IIIB)、(IIIC)和(IV)中,任何P、R1或R2基团可包含一个或多个内酯部分,例如以下结构中之一的基团(其中波浪线表示与单体连接的共价键):
还提供包含一种或多种如本文中所公开的反应的Te单体的聚合物,包括一种或多种上式(I)、(IA)、(IB)、(IC)、(II)、(IIA)、(IIB)、(IIC)、(III)、(IIIA)、(IIIB)、(IIIC)或(IV)中之一的反应的单体。
本发明的优选光致抗蚀剂可包含一种或多种酸产生剂化合物和包含一种或多种如本文中所公开的Te聚合物的聚合物组分。本发明的光致抗蚀剂适当地可以是正作用的或负作用的。
正作用的光致抗蚀剂适当地可包含包括如本文中所公开的酸不稳定基团的组分。酸不稳定基团可以存在于含有一个或多个Te原子的聚合物(Te聚合物),并且/或酸不稳定基团可以存在于另一种光致抗蚀剂组分上,例如不包含Te原子的另一种抗蚀剂树脂。
负作用的光致抗蚀剂适当地可包含交联剂组分,作为单独的组合物或作为抗蚀剂组分的共价连接部分,例如Te聚合物。合适的光致抗蚀剂交联剂包括下文论述的胺基材料作为底层组合物的交联剂。
还提供可被利用的底层组合物,其中将光致抗蚀剂涂布在底层组合物层上面。本发明的底层组合物包含一种或多种如本文中所公开的Te聚合物,并且任选地可包含一种或多种额外的组分,例如交联剂和酸或酸产生剂化合物。优选地,底层涂料组合物可为交联有机膜,并且优选可具有基本上减小的厚度。在某些优选实施例中,底层组合物膜层的干燥厚度是约或更小、或约或更小、约或更小、约或更小、约或更小、约或更小或约或更小。
在一个方面,提供一种方法,其包含将一层包括一种或多种如所公开的Te聚合物的底层组合物涂覆于衬底上;并且将光致抗蚀剂组合物层涂覆于底层涂料组合物层上面。
还提供用于形成本发明光致抗蚀剂组合物的浮雕图像(包括尺寸小于50nm或小于20nm的图案线)的方法。这类方法可包含例如:a)将本发明的光致抗蚀剂涂层涂覆到衬底上;b)将光致抗蚀剂组合物层曝光于包括EUV的活化辐射;以及c)使曝光的光致抗蚀剂组合物涂层显影。
还提供上面涂覆有本发明光致抗蚀剂组合物的衬底,例如微电子晶片。还提供由所公开的方法形成的电子装置。
本发明的其它方面论述于下文中。
具体实施方式
术语Te聚合物是指如本文所公开的聚合物,其包含一个或多个Te原子。
如上文所论述,在一个优选方面,提供加成型聚合物,其包含包括一个或多个Te原子的一个或多个重复单元。如本文所提及的加成聚合物由加成聚合,例如自由基、阳离子、阴离子或配位聚合形成。如本文所提及,加成聚合物可以通过反应形成,其中小分子副产物(例如H2O)或MeOH)不通过反应产生,并且区别于缩合型聚合反应。上式(I)、(IA)、(IB)、(IC)、(II)、(IIA)、(IIB)、(IIC)、(III)、(IIIA)、(IIIB)、(IIIC)和(IV)的优选单体的聚合可提供加成聚合物。在某些优选方面中,可加成聚合物可以通过任何自由基聚合、氮氧化物调控聚合(NMP)、原子转移自由基聚合(ATRP)、可逆的加成-断裂链转移(RAFT)聚合、活性阴离子聚合(LAP)和/或原子转移聚合(ATP)来形成。
又如所论述,在另一优选方面,提供聚合物,其包含一个或多个侧挂到聚合物主链的部分,其中一个或多个侧接部分包含一个或多个Te原子。特别优选的聚合物可包含这类侧链Te部分,但沿聚合物主链没有任何Te原子。上式(I)、(IA)、(IB)、(IC)、(II)、(IIA)、(IIB)、(IIC)、(III)、(IIIA)、(IIIB)、(IIIC)和(IV)的优选单体的聚合可提供这类含Te的侧接部分。
如本文所提及,含Te部分将侧接到聚合物链上,其中所述部分的一个或多个Te原子通过多个基团中的任一个与聚合物主链间隔开,所述基团包括例如烷基(亚烷基);包含碳原子的环基;和/或杂原子,例如氧或任选被取代的硫(例如S(O)、S(O)2),在包含插入聚合物主链与反应性含氮部分之间的1个或多个原子(包括碳原子)、通常1、2、3、4、5、6、7、8、9或10个原子(包括碳原子)的链中。
如所理解,术语聚合物主链是指一系列共价键结的原子,其一起形成聚合物的连续直链。在聚(丙烯酸酯)或聚(烷基丙烯酸酯)(例如聚(甲基丙烯酸酯)树脂)中,侧链Te原子可通过1个或多个原子(包括碳原子)、通过1、2、3、4、5、6、7、8、9或10个原子(包括碳原子)与聚合的丙烯酸酯羧基(-CH2-CH(COO-)-)部分或烷基丙烯酸酯羧基(-CH2-C(烷基)(COO-))部分分隔开。
在某些优选方面,1、2、3、4或5个任选被取代的碳原子(间隔基团)可插入聚合的丙烯酸酯或烷基丙烯酸酯(例如甲基丙烯酸酯)聚合物主链部分与侧接的含Te部分的Te原子之间。
在上式(I)、(IA)、(IB)、(IC)、(II)、(IIA)、(IIB)、(IIC)、(III)、(IIIA)、(IIIB)、(IIIC)和(IV)中,合适的非氢取代基可以是例如卤基(F、Cl、Br或I);氰基、硝基、羟基、任选被取代的C1-20烷基、任选被取代的C1-20烷氧基,例如任选被取代的烷基(例如任选被取代的C1-10烷基);任选被取代的优选地具有2到约20个碳原子的烯基或炔基,例如烯丙基;任选被取代的优选地具有1到约20个碳原子的酮;任选被取代的优选地具有1到约20个碳原子的烷基硫基;任选被取代的优选地具有1到约20个碳原子的烷基亚磺酰基;任选被取代的优选地具有1到约20个碳原子的烷基磺酰基;任选被取代的优选地具有1到约20个碳原子的羧基(其包括例如-COOR′的基团,其中R′是H或C1-8烷基,包括与光酸基本上不反应的酯);任选被取代的烷芳基,例如任选被取代的苯甲基;任选被取代的碳环芳基,例如任选被取代的苯基、萘基、苊基;或任选被取代的杂脂环族或杂芳香族基团,例如吡啶基、呋喃基、吡咯、噻吩、呋喃、咪唑、吡唑、恶唑、异恶唑、噻唑、异噻唑、三唑、呋呫、恶二唑、噻二唑、二噻唑、四唑、吡喃、硫代吡喃、二嗪、恶嗪、噻嗪、二氧杂环己二烯、二噻烷和三嗪,以及含有这类部分中的一个或多个的多芳香族基团。
如本文所提及,术语“亚芳基”是指通过在芳香族环中去除两个氢而获得的具有至少两个价数的官能团,其任选地被指定的一个或多个取代基取代,其限制条件是不超过亚芳基的价数。
如本文所提及,术语“亚杂芳基”是指通过在杂芳香族环中去除两个氢而获得的具有至少两个价数的官能团,其任选地被指定的一个或多个取代基取代,其限制条件是价数不超过亚杂芳基。
如所论述,上式的基团可以在可获得的位置处被一个或多个酸不稳定基团适当地取代。合适的酸不稳定基团可以是多种部分,包括酸不稳定酯和缩醛,例如任选被取代的乙基环戊基酯、甲基金刚烷基酯、乙基金刚烷基酯、叔丁基酯、苯基酯、萘基酯以及其它酯。在某些优选方面,本发明的Te聚合物将含有1或2个共价连接的酸不稳定基团。如本文所提及,在典型光刻处理,包括任何辐射曝露后的热曝露期间,酸不稳定部分或基团(包括酸不稳定酯和缩醛)在产生的酸(来自抗蚀剂中的酸产生剂化合物)存在下进行反应。如本文所提及的酸不稳定基团也可以称为光酸不稳定基团。
可以容易地制备本发明的含Te的单体和聚合物。参见例如下文实例中阐述的合成。
确切地说,本发明的单体化合物包括以下:
如所论述,可优选的是包含酸性或碱反应性基团的单体,所述基团例如醇基(包括卤代醇,例如氟代醇,例如六氟醇(HFA或六氟-2-丙醇))、羧酸基、磺酸基、磺酰胺基或酚基。特别优选的包含酚基的单体包括以下:
包含醇(包括萘酚)、羧酸和卤代醇取代的其它优选单体包括以下:
如所论述,包含一种或多种内酯基团的化合物也可以是优选的,例如以下:
包含一个或多个环氧基的化合物也可以是优选的:
优选的环状烯烃单体包括如下:
包含一个或多个酸不稳定基团的优选化合物包括以下:
优选的聚合物包括以下:
光致抗蚀剂组合物
如上文所论述,如本文所公开的聚合物适用于光致抗蚀剂组合物,包括正作用和负作用化学增幅型抗蚀剂组合物两者。
本发明的光致抗蚀剂通常包含如本文所公开的聚合物和一种或多种光酸产生剂化合物。
本发明的聚合物可包含各种重复单元,其可包含或可能不包含一个或多个Te原子。
举例来说,用于形成本发明聚合物的优选额外单体包括:具有下式(V)的酸不稳定单体、式(VI)的含内酯单体、式(VII)的碱可溶性单体(用于调节碱性显影剂中的溶解速率)和式(VIII)的光酸产生单体或包含至少一种前述单体的组合:
其中每个Ra独立地是H、F、-CN、C1-10烷基或C1-10氟烷基。在式(V)的酸可脱保护单体中,Rb独立地是C1-20烷基、C3-20环烷基、C6-20芳基或C7-20芳烷基,并且每个Rb是独立的或至少一个Rb键结到相邻Rb以形成环状结构。在式(VI)的含内酯单体中,L是单环、多环或稠合多环C4-20含内酯基团。在式(VII)的碱可溶性单体中,W是卤代或非卤代、芳香族或非芳香族C2-50含羟基有机基团,其pKa小于或等于12。在式(VIII)的光酸产生单体中,Q是含酯或不含酯的并且是氟化或非氟化的,并且是C1-20烷基、C3-20环烷基、C6-20芳基或C7-20芳烷基,A是含酯或非含酯的并且是氟化或非氟化的,并且是C1-20烷基、C3-20环烷基、C6-20芳基或C7-20芳烷基,Z-是阴离子部分,其包含羧酸根、磺酸根、磺酰胺阴离子或磺酰亚胺阴离子,并且G+是锍或碘阳离子。
示例性酸不稳定单体包括但不限于:
或包含前述中至少一种的组合,其中Ra是H、F、-CN、C1-6烷基或C1-6氟烷基。
合适的内酯单体可具有下式(IX):
其中Ra是H、F、-CN、C1-6烷基或C1-6氟烷基,R是C1-10烷基、环烷基或杂环烷基,并且w是0到5的整数。在式(IX)中,R直接连接到内酯环上或通常连接到内酯环和/或一个或多个R基团上,并且酯部分直接连接或经由R间接连接到内酯环上。
示例性含内酯的单体包括:
或包含至少一种前述单体的组合,其中Ra是H、F、-CN、C1-10烷基或C1-10氟烷基。
合适的碱可溶性单体可具有下式(X):
其中每个Ra独立地是H、F、-CN、C1-10烷基或C1-10氟烷基,A是含羟基或不含羟基、含酯或不含酯、氟化或非氟化的C1-20亚烷基、C3-20亚环烷基、C6-20亚芳基或C7-20亚芳烷基,并且x是0到4的整数,其中当x是0时,A是含羟基的C6-20亚芳基。
示例性碱可溶性单体包括具有以下结构的单体:
或包含前述中至少一种的组合,其中Ra是H、F、-CN、C1-6烷基或C1-6氟烷基。
优选的光酸产生单体包括式(XI)或式(XII)的单体:
其中每个Ra独立地是H、F、-CN、C1-6烷基或C1-6氟烷基,A是被氟取代的C1-30亚烷基、被氟取代的C3-30亚环烷基、被氟取代的C6-30亚芳基或被氟取代的C7-30亚烷基-亚芳基,并且G+是锍或碘阳离子。
优选地,在式(XI)和式(XII)中,A是[(C(R1)2)xC(=O)O]b-C((R2)2)y(CF2)z-基团或邻位、间位或对位取代的-C6F4-基团,其中每个R1和R2各自独立地是H、F、-CN、C1-6氟烷基或C1-6烷基,b是0或1,x是1到10的整数,y和z独立地是0到10的整数,并且y+z的总和是至少1。
例示性优选的光酸产生单体包括:
或包含前述中至少一种的组合,其中每个Ra独立地是H、F、-CN、C1-6烷基或C1-6氟烷基,k合适地是0到5的整数;并且G+是锍或碘阳离子。
优选的光酸产生单体可包括锍或碘阳离子。优选地,在式(IV)中,G+具有式(XIII):
其中X是S或I;每个R0是卤代或非卤代的并且独立地是C1-30烷基、多环或单环C3-30环烷基、多环或单环C4-30芳基;或包含前述中至少一种的组合,其中当X是S时,R0基团中的一个任选地通过单键连接到一个相邻R0基团,并且a是2或3,其中当X是I时,a是2,或当X是S时,a是3。
示例性酸产生单体包括具有下式的单体:
其中Ra是H、F、-CN、C1-6烷基或C1-6氟烷基。
特别适用于本发明正作用化学增幅型光致抗蚀剂中的具有酸不稳定解块基团的聚合物已经公开于欧洲专利申请0829766A2(具有缩醛的聚合物和缩酮聚合物)和欧洲专利申请EP0783136A2(包括1)苯乙烯;2)羟基苯乙烯;和3)酸不稳定基团(确切地说丙烯酸烷酯酸不稳定基团)的单元的三元共聚物和其它共聚物中。
用于本发明光致抗蚀剂和底层组合物中的Te聚合物的分子量和多分散性可以合适地大幅变化。合适的聚合物包括重量平均Mw是约500或1,000到约50,000、更通常约2,000到约30,000并且分子量分布是约3或更小、更通常分子量分布是约2或更小的聚合物。其它分子量和分子量分布的Te聚合物也是合适的。
本发明的光致抗蚀剂也可以含有其它材料。举例来说,其它任选的添加剂包括光化和对比染料、抗条纹剂、塑化剂、增速剂、敏化剂、光可破坏碱等。这类任选的添加剂通常在光致抗蚀剂组合物中以较小的浓度存在。
包括碱性材料,光可分解阳离子的羧酸盐或磺酸盐优选地提供从酸可分解基团中和酸的机制,并且限制光产生酸的扩散,从而在光致抗蚀剂中提供改善的对比度。
光可破坏碱包括与弱(pKa>2)酸,例如C1-20羧酸的阴离子配对的光可分解的阳离子,以及优选地还适用于制备酸产生剂化合物的碱。示例性的这类羧酸包括甲酸、乙酸、丙酸、酒石酸、琥珀酸、环己基羧酸、苯甲酸、水杨酸和其它这类羧酸。
或者或另外,其它添加剂可包括淬灭剂,其为非光可破坏碱,例如基于氢氧化物、羧酸盐、胺、亚胺和酰胺的碱。优选地,这类淬灭剂包括C1-30有机胺、亚胺或酰胺,或可为强碱(例如氢氧化物或醇盐)或弱碱(例如羧酸盐)的C1-30季铵盐。示例性淬灭剂包括胺,例如三丙胺、十二烷胺、1,1',1"-氮基三丙-2-醇、1,1',1",1"'-(乙烷-1,2-二基双(氮烷三基))四丙-2-醇;芳基胺,例如二苯胺、三苯胺、氨基酚和2-(4-氨基苯基)-2-(4-羟基苯基)丙烷;特罗格氏碱(Troger's base);受阻胺,例如二氮杂双环十一烯(DBU)或二氮杂二环壬烯(DBN);或离子淬灭剂,包括季烷基铵盐,例如氢氧化四丁基铵(TBAH)或乳酸四丁基铵。
表面活性剂包括氟化和非氟化的表面活性剂,并且优选是非离子的。示例性氟化非离子表面活性剂包括全氟C4表面活性剂,例如可购自3M公司的FC-4430和FC-4432表面活性剂;和氟二醇,例如来自欧诺法(Omnova)的POLYFOX PF-636、PF-6320、PF-656和PF-6520氟表面活性剂。
光致抗蚀剂进一步包括一般适用于溶解、施配和涂布光致抗蚀剂中所用组分的溶剂。示例性溶剂包括苯甲醚;醇,包括乳酸乙酯、1-甲氧基-2-丙醇和1-乙氧基-2丙醇;酯,包括乙酸正丁酯、乙酸1-甲氧基-2-丙酯、甲氧基乙氧基丙酸酯、乙氧基乙氧基丙酸酯;酮,包括环己酮和2-庚酮;以及包含前述溶剂中的至少一种的组合。
按固体的总重量计,这类光致抗蚀剂可以50到99重量%、确切地说55到95重量%、更确切地说60到90重量%并且再更确切地说65到90重量%的量包括共聚物。按固体的总重量计,光可破坏碱(如果使用)可以0.01到5重量%、确切地说0.1到4重量%并且再更确切地说0.2到3重量%的量存在于光致抗蚀剂中。按固体的总重量计,可以0.01到5重量%、确切地说0.1到4重量%并且再更确切地说0.2到3重量%的量包括表面活性剂。按固体的总重量计,可以相对较少量,例如0.03到5重量%的量包括淬灭剂。按固体的总重量计,可以小于或等于30重量%、确切地说小于或等于20%或更确切地说小于或等于10%的量包括其它添加剂。按固体和溶剂的总重量计,光致抗蚀剂组合物的总固体含量可以是0.5到50重量%、确切地说1到45重量%、更确切地说2到40重量%并且再更确切地说5到30重量%。酸产生剂化合物应以足以能够在抗蚀剂涂层中产生潜像的量存在。更确切地说,一种或多种酸产生剂化合物将合适地以抗蚀剂总固体的约1到50重量%的量存在。应理解,固体包括共聚物、光可破坏碱、淬灭剂、表面活性剂、任何添加的PAG以及任何任选的添加剂,不包括溶剂。
底层组合物
如上文所论述,还提供了底层涂料组合物,其包含一种或多种如本文所公开的Te聚合物。
在某些实施例中,本发明的底层涂料组合物除了Te聚合物之外或作为其组分(即共价连接)也可包含交联剂。举例来说,底层涂料组合物可包括胺基交联剂,例如三聚氰胺材料,包括例如由氰特工业(Cytec Industries)制造并且以商品名Cymel 300、301、303、350、370、380、1116和1130出售的三聚氰胺树脂;甘脲,包括可购自氰特工业的甘脲;和苯并三聚氰胺和脲基材料,包括树脂,例如可以名称Cymel 1123和1125购自氰特工业的苯并三聚氰胺树脂,和可以名称Powderlink 1174和1196购自氰特工业的脲树脂。除了可商购胺基树脂的外,这类胺基树脂可例如通过使丙烯酰胺或甲基丙烯酰胺共聚物与甲醛在含醇溶液中反应来制备,或者通过使N-烷氧基甲基丙烯酰胺或甲基丙烯酰胺与其它合适的单体共聚来制备。
特别地用于反射控制应用的本发明的涂料组合物还可含有额外的染料化合物,其吸收用于曝露外涂光致抗蚀剂层的辐射。
本发明的底层涂料组合物还可含有其它材料,例如一种或多种酸产生剂化合物,包括一种或多种热酸产生剂和/或光酸产生剂。适用于底层涂料组合物的光酸产生剂包括本文所公开的用于外涂光致抗蚀剂组合物的光酸产生剂。关于光酸产生剂在底层涂料组合物中的这类用途的论述,参见美国专利6261743。
为了制备液体底层涂料组合物,将涂料组合物的组分溶解于合适的溶剂中,例如一种或多种氧基异丁酸酯,特别是2-羟基异丁酸甲酯、乳酸乙酯;或二醇醚中的一种或多种,例如2-甲氧基乙醚(二乙二醇二甲醚)、乙二醇单甲醚和丙二醇单甲醚;具有醚和羟基部分的溶剂,例如甲氧基丁醇、乙氧基丁醇、甲氧基丙醇和乙氧基丙醇;2-羟基异丁酸甲酯;酯,例如溶纤剂乙酸甲酯、溶纤剂乙酸乙酯、丙二醇单甲醚乙酸酯、二丙二醇单甲醚乙酸酯和其它溶剂,例如二元酯、碳酸亚丙酯和γ-丁内酯。
干燥组分(期望溶剂的所有涂料组合物)在溶剂中的浓度将取决于若干因素,例如涂覆方法。底层涂料组合物的固体含量通常在涂料组合物的总重量的约0.1到20重量%之间变化,优选固体含量在涂料组合物的约0.1到10重量之间变化。
光刻处理
经过涂布的衬底可以由含有一或多种如本文所公开的Te聚合物的光致抗蚀剂并且通常由酸产生剂化合物形成,其应以足以能够在抗蚀剂和酸产生剂化合物涂层中产生潜像的量存在。这类经过涂布的衬底包括:(a)在其表面上具有一个或多个待图案化的层的衬底;和(b)在所述一个或多个待图案化的层上方的包括酸产生剂化合物的光致抗蚀剂组合物层。对于EUV或电子束成像,光致抗蚀剂可以合适地具有相对较高的酸产生剂化合物含量,例如其中一种或多种酸产生剂化合物包含抗蚀剂总固体的5到10到约65重量%。通常,较小量的光敏性组分将适用于化学增幅型抗蚀剂。
本发明的光致抗蚀剂一般按照已知程序来进行制备,不同之处在于光致抗蚀剂中包括一种或多种本发明的Te聚合物,并且在某些方面,代替这类光致抗蚀剂配方中所用的先前光敏性化合物。本发明的光致抗蚀剂可以根据已知程序来使用。
衬底可以是任何尺寸和形状,并且优选地是适用于光刻的衬底,例如硅、二氧化硅、绝缘体上硅(silicon-on-insulator,SOI)、应变硅、砷化镓;经涂布的衬底,包括用氮化硅、氮氧化硅、氮化钛、氮化钽涂布的衬底;超薄栅极氧化物,例如氧化铪;金属或金属涂布的衬底,包括用钛、钽、铜、铝、钨、其合金涂布的衬底;以及其组合。优选地,本文的衬底表面包括待图案化的临界尺寸层,包括例如一个或多个栅极层或衬底上用于半导体制造的其它临界尺寸层。这类衬底优选地可包括硅、SOI、应变硅和其它这类衬底材料,形成为具有例如20cm、30cm或更大直径的尺寸或适用于晶片制造生产的其它尺寸的圆形晶片。
此外,一种形成电子装置的方法包括(a)在衬底表面上涂覆光致抗蚀剂组合物层;(b)将光致抗蚀剂组合物层逐图案曝露于活化辐射;以及(c)使曝光的光致抗蚀剂组合物层显影以提供抗蚀剂浮雕图像。
在使用中,本发明的底层涂料组合物通过例如旋涂的多种方法中的任一种以涂层形式涂覆到衬底。通常将涂料组合物涂覆到衬底上并且干燥层厚度在约0.001与0.5μm之间,包含在0.002与0.01μm之间。衬底宜为用于涉和光致抗蚀剂的方法中的任何衬底。举例来说,衬底可为硅、二氧化硅或铝-氧化铝微电子晶片。还可采用砷化镓、碳化硅、陶瓷、石英或铜衬底。
在某些方面,包括EUV成像,底层涂料组合物可宜涂覆在硬掩模层上。
优选在将光致抗蚀剂组合物涂覆到底层涂料组合物上面之前,固化所涂覆的底层涂层。固化条件将随底层涂料组合物的组分而变化。特别地,固化温度将取决于涂料组合物中采用的特定酸或酸(例如热)产生剂。典型的固化条件为在约60℃到225℃下进行约0.5到5分钟。固化条件优选使涂料组合物涂层基本上不溶于光致抗蚀剂溶剂以及待使用的显影剂溶液中。
在这类固化之后,在所涂覆涂料组合物的表面上面涂覆光致抗蚀剂。与底层涂料组合物层的涂覆一样,外涂光致抗蚀剂可通过任何标准方式(例如通过旋涂、浸渍、弯液面涂布或辊涂)来涂覆。在涂覆之后,通常通过加热来干燥光致抗蚀剂涂层以去除溶剂优选直到抗蚀剂层不粘。最理想地,大体上不会互混底部组合物层和外涂光致抗蚀剂层。
随后,以常规方式用活化辐射(例如248nm、193nm或EUV辐射)经由掩模使抗蚀剂层成像。曝露能量足以有效地激活抗蚀剂系统的光敏性组分以在抗蚀剂涂层中产生图案化图像。通常,曝露能量在约3到300mJ/cm2范围内并且部分地取决于曝露工具和所采用的特定抗蚀剂和抗蚀剂处理。如果需要,可使曝露抗蚀剂层经受曝露后烘烤以形成或增强涂层的曝露区域与未曝露区域之间的溶解度差异。举例来说,负性酸硬化光致抗蚀剂通常需要曝露后加热以诱发酸促进的交联反应,并且许多化学增幅型正作用抗蚀剂需要曝露后加热以诱发酸促进的脱保护反应。典型的曝露后烘烤条件包括约50℃或更高的温度、更确切地说在约50℃到约160℃的范围内的温度。
随后,曝光的光致抗蚀剂层的显影通过用能够选择性地去除曝光膜部分(其中光致抗蚀剂是正型)或去除未曝光膜部分(其中光致抗蚀剂在曝光区域中可交联,即是负型)的合适显影剂处理曝光层来实现。优选地,光致抗蚀剂是基于具有酸敏感性(可脱保护)基团的聚合物的正型,并且显影剂优选地是无金属离子的氢氧化四烷基铵溶液,例如0.26N氢氧化四甲基铵水溶液。图案通过显影形成。
另外,对于正性抗蚀剂,未曝光区可以通过用合适于负型显影的非极性溶剂处理来选择性地去除。适于正性光致抗蚀剂的负型显影的程序参见U.S.2011/0294069。用于负型显影的典型非极性溶剂是有机显影剂,例如选自酮、酯、烃和其混合物的溶剂,例如丙酮、2-己酮、乙酸甲酯、乙酸丁酯以及四氢呋喃。
当用于一种或多种这类图案形成工艺中时,光致抗蚀剂可以用于制造电子和光电装置,例如存储器装置、处理器芯片(CPU)、图形芯片以及其它这类裝置。
以下实例是对本发明的说明。
实例1-3:单体合成
实例1:M1合成
单体M1的合成的反应示于以下流程1中。碲吩衍生物1的合成描述于Ahmad,Sohail等人,《有机化学期刊(Journal of Organic Chemistry)》,80(8),3880-3890;2015及Ahmad,Sohail等人,《RSC进展(RSC Advances)》,4(7),3171-3180;2014中。向反应烧瓶中装入2,2'-(碲吩-2,5-二基)双(丙-2-醇)(化合物1,15.0g,50.7mmol)于150mL的二氯甲烷中的溶液。将溶液冷却到0℃。将甲基丙烯酰氯(3.53g,33.8mmol)和三乙胺(3.54g,35.0mmol)添加到反应烧瓶中,并且将混合物在室温下搅拌16h。将有机相用水(3×100mL)洗涤,并且在减压下完全去除溶剂。通过硅胶柱色谱法纯化粗材料。收集含有产物的溶剂洗脱份,并且在减压下完全去除溶剂以产生单体M1。
流程1:
实例2:M2合成
单体化合物M2的合成的反应步骤示于以下流程2中。双(4-羟基苯基)碲化物(2)的合成由S.Zhang等人,《四面体快报(Tetrahedron Letters)》,54(20),2452-2454;2013描述。溴乙酸1-乙基环戊酯(3)的合成由Thackeray,James W.等人描述于US 20140080062中。向化合物2(10.0g,31.80mmol)于75mL N,N-二甲基甲酰胺中的溶液中添加氯乙酸叔丁酯(6.0g,31.50mmol)和4.40g碳酸钾。将混合物在惰性气氛下在80℃下搅拌6小时,冷却到室温并且倒入150mL水中以产生残余物,其包含所需产物4和其它有机组分的混合物。通过柱色谱法将产物4与其它组分分离。在下一步骤中,向反应烧瓶中装入化合物4(10.0g,21.36mmol)于50mL二氯甲烷中的溶液。将溶液冷却到0℃。将甲基丙烯酰氯(2.23g,21.36mmol)和三乙胺(2.5g,24.7mmol)添加到反应烧瓶中,并且将混合物在室温下搅拌16h。将有机相用水(3×75mL)洗涤,并且在减压下完全去除溶剂。通过硅胶柱色谱法纯化粗材料。收集含有产物的溶剂洗脱份,并且在减压下完全去除溶剂以产生单体M2。
流程2:
实例3:M3合成
单体化合物M3的合成的反应步骤示于以下流程3。向反应烧瓶中装入化合物2(10.0g,31.86mmol)于50mL二氯甲烷中的溶液。将溶液冷却到0℃。将甲基丙烯酰氯(3.32g,31.86mmol)和三乙胺(2.5g,24.7mmol)添加到反应烧瓶中,并且将混合物在室温下搅拌16h。将有机相用水(3×75mL)洗涤,并且在减压下完全去除溶剂。通过硅胶柱色谱法纯化粗材料。收集含有产物的溶剂洗脱份,并且在减压下完全去除溶剂以产生单体M3。
流程3
实例4:聚合物合成
这一实例描述本发明和比较共聚物的合成。用于合成每种聚合物的单体的摩尔比率阐述下表1中。单体的结构示于下面的流程4中。以下程序用于合成聚合物1(P1)。单体MAMA(10.16g,0.058mol)、单体aGBLMA(8.31g,0.066mol)%和单体HAMA(5.17g,0.022mol)于48g丙二醇单甲醚乙酸酯(“PGMEA”)和引发剂偶氮引发剂二甲基2,2'-偶氮双(2-甲基丙酸酯)(2.5g)在氮气氛围下经加热8小时。将反应冷却到室温并且倒入甲醇中以产生聚合物P1,将其过滤并且干燥。
使用与用于制备共聚物1(P1)相似的程序制备下表1中阐述的额外的聚合物(P2、P3、P4、P5),不同之处在于使用如表1中指定的单体类型和摩尔进料比。
流程4:
表1
实例5:光致抗蚀剂组合物制备
用于PTD(正型显影)应用的光致抗蚀剂制备的通用程序。将38.85g聚合物溶液(在聚合物的PGMEA中15%,例如以上实例4中所描述的P2、P3、P4或P5)、31.04g三苯基锍三氟甲磺酸酯(TPS Tf)(在甲基-2-羟基异丁酸酯中2%)和5.03g(1,3-二羟基-2-(羟甲基)丙-2-基)氨基甲酸叔丁酯溶液(在甲基-2-羟基异丁酸酯中1%)混合并且用尼龙过滤器过滤,得到光致抗蚀剂组合物
实例6:底层组合物
将0.14g以上实例4中所描述的聚合物P1、0.012g作为交联剂的四甲氧基甲基甘脲、0.002g 2,4,6-三甲基吡啶鎓对甲苯磺酸酯溶于82g甲基-2-羟基异丁酸酯溶剂中,以获得流体底层涂料组合物。将制备的流体组合物通过PTFE分子量聚乙烯膜过滤器过滤。然后在1500rpm下将过滤的底层涂料组合物旋涂在硅晶片上,使用a和如此涂覆的晶片在205℃下在热板上加热1分钟。
实例7:光刻处理
如实例5中制备的光致抗蚀剂组合物旋涂在300mm硅晶片上的硬化的有机涂层上,随后在100℃下进行60秒钟的软烘烤。通过掩模将抗蚀剂涂层曝露于图案化的EUV辐射。将曝光的晶片在100℃下烘烤60秒,并且抗蚀剂层在2.38%的氢氧化四甲基铵(TMAH)中显影来提供浮雕图像。
实例8:进一步的光刻处理
如实例5中制备的光致抗蚀剂组合物旋涂在如实例6中制备的烘烤涂层上,随后在100℃下软烘烤60秒。通过掩模将抗蚀剂涂层曝露于图案化的EUV辐射。将曝光的晶片在100℃下烘烤60秒,并且抗蚀剂层在2.38%的氢氧化四甲基铵(TMAH)中显影来提供浮雕图像。
实例9:EUV透射率计算
下表2显示比较和本发明组合物的组成,所述组合物以20重量%各自包含聚合物和光酸产生剂三苯基锍三氟甲磺酸酯(TPS Tf)。本发明组合物C2、C3、C4和C5分别包含本发明聚合物P2、P3、P4和P5。由组合物实例制成的膜在EUV曝光(13.5nm)下的透射是由X射线光学器件中心(the Center for X-Ray Optics)在劳伦斯伯克利国家实验室(LawrenceBerkeley National Laboratory)网站通过输入所计算的组合物分子式并且假设膜密度是1.20g/cm3并且膜厚度是60nm来计算。从表2中可以看出,对于包含本发明实例的配方,能获得较少的透射。这些数据证实含碲聚合物的PAG吸收显著增加。
表2
Claims (4)
2.一种结合光致抗蚀剂使用的底层涂料组合物,所述涂料组合物包含一种或多种根据权利要求1中所定义的聚合物。
3.一种用于提供光致抗蚀剂浮雕图像的方法,其包含:
a)在衬底上涂覆根据权利要求1所述的光致抗蚀剂组合物的涂层;以及
b)使所述光致抗蚀剂组合物层曝露于活化辐射并且使所述曝露的光致抗蚀剂组合物层显影。
4.一种用于提供光致抗蚀剂浮雕图像的方法,其包含:
a)在衬底上涂覆根据权利要求2所述的底层涂料组合物层;
b)在所述底层涂料组合物层上面涂覆光致抗蚀剂组合物层;和
c)使所述光致抗蚀剂组合物层曝露于活化辐射并且使所述曝露的光致抗蚀剂组合物层显影。
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