CN1313880C - 光致抗蚀剂聚合物、含有其的组合物和图案形成方法 - Google Patents

光致抗蚀剂聚合物、含有其的组合物和图案形成方法 Download PDF

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CN1313880C
CN1313880C CNB2004100618320A CN200410061832A CN1313880C CN 1313880 C CN1313880 C CN 1313880C CN B2004100618320 A CNB2004100618320 A CN B2004100618320A CN 200410061832 A CN200410061832 A CN 200410061832A CN 1313880 C CN1313880 C CN 1313880C
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郑载昌
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Abstract

本发明涉及光致抗蚀剂聚合物及含有该光致抗蚀剂聚合物的光致抗蚀剂组合物。小于50纳米的光致抗蚀剂图案是使用EUV(极远紫外线)作为曝光光源，由包含下列成份的光致抗蚀剂组合物来获得的：(i)包含式2聚合重复单元的光致抗蚀剂聚合物或(ii)包含式3聚合重复单元的光致抗蚀剂聚合物与聚乙烯基苯酚。结果，虽然该光致抗蚀剂图案具有极小的厚度，但仍可取得优越的抗蚀刻性。其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、a、b、c、d、e、f及g如说明书中所定义。

Description

光致抗蚀剂聚合物、含有其的组合物和图案形成方法
                        技术领域
本发明公开了光致抗蚀剂聚合物及含有该光致抗蚀剂聚合物的光致抗蚀剂组合物，其适用于使用远紫外光区诸如EUV(极远紫外线，13纳米)的光源的光刻法(photolighography)，以制造高度集成半导体装置的超细电路。
                        背景技术
近来，为了在超细电路形成方法中达到较高的灵敏度，已对化学放大型深紫外线(DUV)光致抗蚀剂进行了研究。此类光致抗蚀剂可通过混合光酸生成剂(photoacid generator)与具有酸不稳定基团的基质聚合物而制备。
根据该光致抗蚀剂的反应机制，光酸生成剂在通过紫外线光源照射时产生酸，该基质聚合物的主链或支链在后续的烘烤过程中与所生成的酸反应而分解或交联，使得该聚合物的极性相当程度地改变。此种极性的变化使得曝光区与未曝光区在显影溶液中的溶解度产生差异。
例如，如果为正型光致抗蚀剂，则酸是在曝光区生成，所生成的酸在后续烘烤过程中与基质聚合物反应，使得该聚合物的主链或支链在后续显影过程中分解并溶解。然而，因为未曝光区并未生成酸，保持该聚合物的原始结构且在后续显影过程中不溶解，因此在基材上形成掩模(mask)的正像。
在任何光刻方法中，分辨率都与光源的波长有关。当光源的波长变得较小时，可形成愈细的图案。就形成小于50纳米的图案所需的曝光设备而言，正在开发EUV设备，也正在开发用于小于50纳米图案的改良光致抗蚀剂。对于光致抗蚀剂，预测要成功地形成小于50纳米的图案存在重大的问题。例如，一方面，光致抗蚀剂需要在极薄的膜中沉积，但另一方面，薄膜无法确保充分的抗蚀刻性。因此，需要一种具有优越的抗蚀刻性的改良光致抗蚀利，其可在极薄的膜中沉积，以形成小于50纳米的图案。
                        发明内容
因此，本发明公开了光致抗蚀剂聚合物及含有该光致抗蚀剂聚合物的光致抗蚀剂组合物，其可应用于光刻方法，尤其是使用EUV的光刻方法，来形成小于50纳米的超细图案。
本发明也公开了一种使用前述光致抗蚀剂组合物形成光致抗蚀剂图案的方法，及使用前述光致抗蚀剂组合物制得的半导体装置。
                        附图说明
图1是由实施例1制得的光致抗蚀剂聚合物的NMR光谱。
图2是由实施例2制得的光致抗蚀剂聚合物的NMR光谱。
图3是由实施例6制得的接触孔图案的相片。
图4是由实施例7通过抗蚀剂(resist)流动方法制得的接触孔图案的相片。
                      具体实施方式
公开了一种光致抗蚀剂聚合物，其包含式1所示的聚合重复单元：
式1
Figure C20041006183200071
其中R1是氢或甲基；且
R5是直链或支链C1-C10亚烷基。
式1的聚合重复单元包含具有优越抗蚀刻性的蒽型单体。
该光致抗蚀剂聚合物优选包含式2或3所示的聚合重复单元：
式2
其中R1、R2、R3及R4独立地为氢或甲基；
R5及R6独立地为直链或支链C1-C10亚烷基；
R7是酸不稳定保护基；且
a∶b∶c∶d＝20～60摩尔％∶5～20摩尔％∶3～15摩尔％∶20～50摩尔％。
式3
其中R8、R9及R10独立地为氢或甲基；
R11是直链或支链C1-C10亚烷基；
R12是酸不稳定保护基；且
e∶f∶g＝30～60摩尔％∶5～25摩尔％∶30～50摩尔％。
式2的聚合重复单元的优选实例为聚(甲基丙烯酸9-蒽甲酯/甲基丙烯酸2-羟乙酯/丙烯酸叔丁酯/丙烯酸)，式3的聚合重复单元的实例优选为聚(甲基丙烯酸9-蒽甲酯/丙烯酸叔丁酯/丙烯酸)。
酸不稳定保护基是指通过酸可分离的基团，酸不稳定保护基防止该光致抗蚀剂在键合有该酸不稳定保护基时溶解在碱性的显影溶液中。若该酸不稳定保护基通过酸曝露而分离，则该光致抗蚀剂可溶解在碱性溶液中。
该酸不稳定保护基可为任何已知的保护基，一些常规的酸不稳定保护基公开在美国专利第5,212,043号(1993年5月18日)、WO 97/33198(1997年9月12日)、WO 96/37526(1996年11月28日)、EP 0794458(1997年9月10日)、EP 0789278(1997年8月13日)、美国专利第5,750,680号(1998年5月12日)、美国专利第6,051,678号(2000年4月18日)、GB 2,345,286A(2000年7月5日)、美国专利第6,132,926号(2000年10月17日)、美国专利第6,143,463号(2000年11月7日)、美国专利第6,150,069号(2000年11月21日)、美国专利第6,180,316B 1号(2001年1月30日)、美国专利第6,225,020 B1号(2001年5月1日)、美国专利第6,235,448B 1号(2001年5月22日)及美国专利第6,235,447 B1号(2001年5月22日)。该酸不稳定保护基包括，但不限于，任何选自下列的基团：叔丁基、四氢吡喃-2-基、2-甲基四氢吡喃-2-基、四氢呋喃-2-基、2-甲基四氢呋喃-2-基、1-甲氧基丙基、1-甲氧基-1-甲基乙基、1-乙氧基丙基、1-乙氧基-1-甲基乙基、1-甲氧基乙基、1-乙氧基乙基、叔丁氧基乙基、1-异丁氧基乙基及2-乙酰基薄荷(menth)-1-基。
本发明也公开了一种正型光致抗蚀剂组合物，其包含作为基质树脂的前述光致抗蚀剂聚合物、光酸生成剂及有机溶剂。
该基质树脂包含(i)包含式2聚合重复单元的光致抗蚀剂聚合物或(ii)包含式3聚合重复单元的光致抗蚀剂聚合物与聚乙烯基苯酚。
当该基质树脂含有包含式3聚合重复单元的光致抗蚀剂聚合物与聚乙烯基苯酚时，该聚乙烯基苯酚优选以基于包含式3聚合重复单元的光致抗蚀剂聚合物的5至20重量％的量存在。
该光酸生成剂可选自任何可通过光生成酸的常规的化合物，包括例如前述已知文件中所公开的化合物。其中，优选使用硫化物型或鎓型化合物来作为光酸生成剂。
优选的光酸生成剂是一种或多种选自下列的化合物：六氟磷酸二苯基碘、六氟砷酸二苯基碘、六氟锑酸二苯基碘、三氟甲磺酸二苯基对-甲氧基苯基锍、三氟甲磺酸二苯基对-甲苯基锍、三氟甲磺酸二苯基对-异丁基苯基锍、三氟甲磺酸二苯基对-叔丁基苯基锍、六氟磷酸三苯基锍、六氟砷酸三苯基锍、六氟锑酸三苯基锍、三氟甲磺酸三苯基锍、三氟甲磺酸二丁基萘基锍、苯二甲酰亚氨基三氟甲烷磺酸酯、二硝基苄基甲苯磺酸酯、正癸基二砜、萘基亚氨基三氟甲烷磺酸酯及下式4的化合物。其中，该光酸生成剂以基于该光致抗蚀剂聚合物的1至8重量％的量存在。已发现当该光酸生成剂用量低于1重量％时，光致抗蚀剂的感光灵敏度降低。然而，当用量高于8重量％时，该光酸生成剂吸收远紫外光射线并生成大量的酸，由于显影过程之后的溶解度，因而得到较差的图案并生成粒子。
式4
Figure C20041006183200101
任何常规的有机溶剂都可用在光致抗蚀剂组合物中，包含例如前述文件中所公开的常规的溶剂。该有机溶剂优选包含任何选自下列的组：3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、丙二醇甲基醚乙酸酯、环己酮、2-庚酮、乳酸乙酯及其混合物。该有机溶剂以基于该光致抗蚀剂聚合物的500至8000重量％的量存在，以得到具有所需厚度的光致抗蚀剂薄膜。
所公开的用于形成光致抗蚀剂图案的方法(以下称为″图案化方法″)包含：
(a)将该光致抗蚀剂组合物涂覆在底层的顶部，以形成光致抗蚀剂薄膜；
(b)使该光致抗蚀剂薄膜曝露于光线下；及
(c)将经曝光的光致抗蚀剂薄膜显影，以得到光致抗蚀剂图案。
图案化方法可进一步包含在步骤(b)之前进行的温和烘烤过程或在步骤(b)之后进行的后烘烤过程。该烘烤过程优选在70至200℃的温度下进行。
曝光过程优选使用选自EUV(13纳米)、VUV(157纳米)、E-束、X-束及离子束的光源，以1至100毫焦耳/厘米2的曝光能量进行。
显影过程(c)可使用碱性显影溶液进行，该碱性显影溶液优选0.01至5重量％的TMAH水溶液。
根据所公开正型光致抗蚀剂的机制，该光酸生成剂在曝露于来自光源的紫外线时生成酸。在曝光后的烘烤过程中，该酸与包含式2重复单元的聚合物反应，并分离该酸不稳定保护基。结果，聚合物的支链分解并在后续显影过程中溶解在碱性显影溶液中。或使该酸与包含式3重复单元的聚合物反应，并在曝光后的烘烤过程中分离该酸不稳定保护基。结果，聚合物的支链分解并在后续显影过程中溶解在碱性显影溶液中。在此情况下，聚乙烯基苯酚本身溶解在碱性显影溶液中，因此，显影过程不产生问题。
另一方面，因为在未曝光区域中未生成酸，则包含式2或3重复单元的聚合物不溶解，因而得到掩模影像的正像。
当使用包含式3重复单元的聚合物与聚乙烯基苯酚一起作为基质树脂时，若在形成光致抗蚀剂图案之后进行抗蚀剂流动过程，则在该包含式3重复单元的聚合物中的羧酸与该聚乙烯基苯酚之间发生酯化而生成交联键。该光致抗蚀剂图案通过该种键联，流动后保持其型式。如此，可通过添加作为基质树脂的聚乙烯基苯酚，来改善光致抗蚀剂图案的流动特性。若不使用聚乙烯基苯酚，则预见的问题是可能在抗蚀剂流动过程中发生光致抗蚀剂图案的变形。
此外也公开了使用前述光致抗蚀剂组合物制得的半导体装置。
下文参照以下非限制性实施例更详细地描述所公开的光致抗蚀剂聚合物及含有该光致抗蚀剂聚合物的光致抗蚀剂组合物。
实施例1：光致抗蚀剂聚合物(1)的制备
向50克丙二醇甲基醚乙酸酯(PGMEA)中添加5克甲基丙烯酸9-蒽甲酯、1克甲基丙烯酸2-羟基乙酯、3克丙烯酸叔丁酯、1克丙烯酸及0.4克AIBN。将所制备的溶液在66℃下反应8小时。反应之后，将形成的混合物在乙醚中沉淀，过滤，在真空条件下干燥，以得到分子量为12,500的聚(甲基丙烯酸9-蒽甲酯/甲基丙烯酸2-羟基乙酯/丙烯酸叔丁酯/丙烯酸)(产率：88％)(参照图1的NMR光谱)。
实施例2：光致抗蚀剂聚合物(2)的制备
向50克PGMEA中添加6克甲基丙烯酸9-蒽甲酯、3克丙烯酸叔丁酯、1克丙烯酸及0.8克AIBN。将所制备的溶液在66℃下反应8小时。反应之后，将形成的混合物在乙醚中沉淀，过滤，在真空条件下干燥，以得到分子量为11,200的聚(甲基丙烯酸9-蒽甲酯/丙烯酸叔丁酯/丙烯酸)(产率：80％)(参照图2的NMR光谱)。
实施例3：光致抗蚀剂组合物(1)的制备
向13克作为有机溶剂的PGMEA中添加1克实施例1中所制得的聚(甲基丙烯酸9-蒽甲酯/甲基丙烯酸2-羟基乙酯/丙烯酸叔丁酯/丙烯酸)及0.04克作为光酸生成剂的三氟甲磺酸三苯基锍。将形成的混合物在0.20微米的过滤器中过滤，以得到光致抗蚀剂组合物。
实施例4：光致抗蚀剂组合物(2)的制备
向200克作为有机溶剂的环己酮中添加9克实施例2中所制得的聚(甲基丙烯酸9-蒽甲酯/丙烯酸叔丁酯/丙烯酸)、1克分子量为4,000的聚乙烯基苯酚及0.5克作为I-线的光酸生成剂的式4化合物。将形成的混合物在0.20微米的过滤器中过滤，以得到光致抗蚀剂组合物。
实施例5：光致抗蚀剂薄膜的形成
将实施例3中所制得的光致抗蚀剂组合物在3000厚度下旋涂于硅晶片上以形成光致抗蚀剂薄膜，并在130℃下烘烤90秒。烘烤之后，将光致抗蚀剂薄膜使用CF4与Ar的混合气体蚀刻。发现光致抗蚀剂薄膜的蚀刻速度与在相同厚度下形成并蚀刻的KrF光致抗蚀剂薄膜比较约为80％，由此证明改良的抗蚀刻性。
实施例6：接触孔图案的形成
将实施例4中所得的光致抗蚀剂组合物旋涂在硅晶片上以形成光致抗蚀剂薄膜，在120℃下烘烤90秒。烘烤之后，该光致抗蚀剂薄膜使用I-线曝光装置曝光。完成烘烤过程之后，将烘烤的薄膜在2.38重量％TMAH水溶液中显影40秒，以得到300纳米的接触孔图案(参照图3)。
实施例7：抗蚀剂流动特性的评估
将实施例6中所得的300纳米的接触孔图案在160℃下烘烤90秒，以评估其抗蚀剂流动特性。结果，发现该接触孔图案因为抗蚀剂流动而缩小成218纳米，并未发生图案变形(参照图4)。
如前文所述，因为光致抗蚀剂图案是通过使用包含具有优越抗蚀刻性的蒽型化合物的正型光致抗蚀剂组合物形成的，所以虽然该光致抗蚀剂图案具有较小的厚度，但仍可通过使用EUV作为曝光光源来形成具有优越抗蚀刻性且小于50纳米的光致抗蚀剂图案。

Claims (18)

1.一种光致抗蚀剂聚合物，其包含式2或3所示的聚合重复单元：
式2
其中R1、R2、R3及R4独立地为氢或甲基；
R5及R6独立地为直链C1-C10亚烷基或支链C1-C10亚烷基；
R7是酸不稳定保护基；且
a∶b∶c∶d＝20～60摩尔％∶5～20摩尔％∶3～15摩尔％∶20～50摩尔％，
式3
其中R8、R9及R10独立地为氢或甲基；
R11是直链C1-C10亚烷基或支链C1-C10亚烷基；
R12是酸不稳定保护基；且
e∶f∶g＝30～60摩尔％∶5～25摩尔％∶30～50摩尔％。
2.根据权利要求1的光致抗蚀剂聚合物，其中式2的聚合重复单元是聚(甲基丙烯酸9-蒽甲酯/甲基丙烯酸2-羟基乙酯/丙烯酸叔丁酯/丙烯酸)，且
式3的聚合重复单元是聚(甲基丙烯酸9-蒽甲酯/丙烯酸叔丁酯/丙烯酸)。
3.根据权利要求1的光致抗蚀剂聚合物，其中该酸不稳定保护基选自下列的基团：叔丁基、四氢吡喃-2-基、2-甲基四氢吡喃-2-基、四氢呋喃-2-基、2-甲基四氢呋喃-2-基、1-甲氧基丙基、1-甲氧基-1-甲基乙基、1-乙氧基丙基、1-乙氧基-1-甲基乙基、1-甲氧基乙基、1-乙氧基乙基、叔丁氧基乙基、1-异丁氧基乙基及2-乙酰基薄荷-1-基。
4.一种光致抗蚀剂组合物，其包含：
作为基质树脂的含有式2聚合重复单元的光致抗蚀剂聚合物；
光酸生成剂；及
有机溶剂：
式2
Figure C2004100618320003C1
其中R1、R2、R3及R4独立地为氢或甲基；
R5及R6分别为直链C1-C10亚烷基或支链C1-C10亚烷基；
R7是酸不稳定保护基；且
a∶b∶c∶d＝20～60摩尔％∶5～20摩尔％∶3～15摩尔％∶20～50摩尔％。
5.一种光致抗蚀剂组合物，其包含聚乙烯基苯酚和作为基质树脂的包含式3聚合重复单元的光致抗蚀剂聚合物；
光酸生成剂；和
有机溶剂；
其中，式3
其中R8、R9及R10独立地为氢或甲基；
R11是直链C1-C10亚烷基或支链C1-C10亚烷基；
R12是酸不稳定保护基；且
e∶f∶g＝30～60摩尔％∶5～25摩尔％∶30～50摩尔％。
6.根据权利要求5的光致抗蚀剂组合物，其中该聚乙烯基苯酚以基于包含式3聚合重复单元的光致抗蚀剂聚合物的5至20重量％的量存在。
7.根据权利要求4或5的光致抗蚀剂组合物，其中该光酸生成剂是一种或多种选自下列的化合物：六氟磷酸二苯基碘、六氟砷酸二苯基碘、六氟锑酸二苯基碘、三氟甲磺酸二苯基对-甲氧基苯基锍、三氟甲磺酸二苯基对-甲苯基锍、三氟甲磺酸二苯基对-异丁基苯基锍、三氟甲磺酸二苯基对-叔丁基苯基锍、六氟磷酸三苯基锍、六氟砷酸三苯基锍、六氟锑酸三苯基锍、三氟甲磺酸三苯基锍、三氟甲磺酸二丁基萘基锍、苯二甲酰亚氨基三氟甲烷磺酸酯、二硝基苄基甲苯磺酸酯、正癸基二砜、萘基亚氨基三氟甲烷磺酸酯及式4的化合物
式4
Figure C2004100618320004C2
8.根据权利要求4或5的光致抗蚀剂组合物，其中该光酸生成剂以基于该基质树脂的1至8重量％的量存在。
9.根据权利要求4或5的光致抗蚀剂组合物，其中该有机溶剂选自：3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、丙二醇甲基醚乙酸酯、环己酮、2-庚酮、乳酸乙酯及其混合物。
10.根据权利要求4或5的光致抗蚀剂组合物，其中该有机溶剂以基于该基质树脂的500至8000重量％的量存在。
11.根据权利要求5的光致抗蚀剂组合物，其中该组合物用于抗蚀剂流动过程。
12.一种形成光致抗蚀剂图案的方法，所述方法包含：
(a)将权利要求4的光致抗蚀剂组合物涂覆在底层的顶部，以形成光致抗蚀剂薄膜；
(b)使该光致抗蚀剂薄膜曝露于光线下；及
(c)将经曝光的光致抗蚀剂薄膜显影，以得到光致抗蚀剂图案。
13.一种形成光致抗蚀剂图案的方法，所述方法包含：
(a)将权利要求5的光致抗蚀剂组合物涂覆在底层的顶部，以形成光致抗蚀剂薄膜；
(b)使该光致抗蚀剂薄膜曝露于光线下；及
(c)将经曝光的光致抗蚀剂薄膜显影，以得到第一光致抗蚀剂图案。
14.根据权利要求13的方法，其进一步包含在(c)部分之后进行抗蚀剂流动过程，以得到第二光致抗蚀剂图案。
15.根据权利要求12或13中任一项的方法，其进一步包含在(b)部分之前进行温和烘烤过程，或在(b)部分之后进行后烘烤过程。
16.根据权利要求12的方法，其中该光源选自EUV、VUV、E-束、X-束及离子束。
17.一种根据权利要求12的方法制得的半导体装置。
18.一种根据权利要求13的方法制得的半导体装置。
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