CN114544803A - 一种光刻胶树脂单体丙烯酸酯类化合物的hplc分析方法 - Google Patents
一种光刻胶树脂单体丙烯酸酯类化合物的hplc分析方法 Download PDFInfo
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Abstract
本发明提供了一种光刻胶树脂单体丙烯酸酯类化合物的HPLC分析方法,该方法为采用正相高效液相色谱法,流动相为小极性烷烃溶剂或小极性烷烃溶剂与色谱纯醇的混合溶液,使用紫外检测器对丙烯酸酯类树脂单体进行等度洗脱。本发明方法具有专属性强、方法操作简单、灵敏度高、易于标准化操作优点,可用于树脂单体丙烯酸酯类产品工业化分析检测,提高树脂单体丙烯酸酯类产品工业化生产检测的准确性。
Description
技术领域
本发明属于化学分析技术领域,具体涉及一种光刻胶树脂单体丙烯酸酯类化合物的HPLC分析方法。
背景技术
光刻胶树脂丙烯酸酯类产品是最早一代的193nm光刻胶用树脂。从90年代后半期开始,光刻光源就开始采用248nm的KrF激光;而从2000年代开始,光刻就进一步转向使用193nm波长的ArF准分子激光作为光源。直至今天的20多年里,193nm波长的ArF准分子激光一直是半导体制程领域性能最可靠,使用最广泛的光刻光源。
193nm光刻胶主要用于高端手机、个人电脑/服务器CPU、中高端手机基带、CPU、显卡图形处理器、蓝牙芯片、电源管理芯片、显示芯片等芯片的制作,随着各类高端手机、电子产品的不断更新换代,芯片制作中对于193nm光刻胶的需求量越来越大。同时,丙烯酸酯系列类产品的质量纯度也直接影响光刻胶的感光速度、优良的操作宽度及抗蚀性能,从而直接影响芯片的性能,因此,丙烯酸酯类产品的质量分析已然成为重中之中,急需一种准确可靠的分析方法来为丙烯酸酯类产品的质量把关,提高我国丙烯酸酯系列产品的竞争力。
Kubota N,Hayashi T等人在文献Advanced resist design using AFM analysisfor ArF lithography.中采用IR和NMR检测方法对产品进行了检测,结构确证,而IR和NMR多用于产品结构确证及产品定性分析,NMR多为半定量且误差大,较少用于产品定量分析。同样,在专利JP 2015143307A中,同样采用NMR与IR来对产品进行分析检测。个别文献采用GC方法,考虑到丙烯酸酯产品低温保存,保存条件为30℃以下,GC在分析过程温度高达250℃,易产生杂质干扰检测结果。
发明内容
为使丙烯酸酯类产品达到日常定性定量分析,本发明提供了一种光刻胶树脂单体丙烯酸酯类化合物的HPLC分析方法,降低丙烯酸酯类树脂单体因高温易聚合的可能性,具有专属性强、方法操作简单、灵敏度高、易于标准化操作优点,可用于丙烯酸酯类产品工业化分析检测,提高丙烯酸酯类产品工业化生产检测的准确性。
本发明采用的技术方案是:采用正相高效液相色谱法,流动相为小极性烷烃与色谱纯醇的混合溶液,其中小极性烷烃的体积分数为80-100%,余量为色谱纯醇;使用紫外检测器通过等度洗脱对丙烯酸酯类树脂单体进行分析检测。当流动相中的小极性烷烃的体积分数为100%时,流动相为小极性烷烃溶剂。
进一步地,所述树脂单体丙烯酸酯类化合物为:2-乙基-2-金刚烷基甲基丙烯酸酯、2-乙基-2-金刚烷基丙烯酸酯、2-甲基-2-金刚烷基甲基丙烯酸酯、2-甲基-2-金刚烷基丙烯酸酯、2-金刚烷基甲基丙烯酸酯、2-金刚烷基丙烯酸酯、2-羰基-四氢呋喃-3-羟基-丙烯酸酯、2-羰基-四氢呋喃-3-羟基-甲基丙烯酸酯、2-甲基-2-丙烯酸-4-羟基苯基酯或4-羟基苯基丙烯酸酯。
进一步地,所述流动相中的小极性烷烃为正己烷或环己烷。
进一步地,所述流动相中的色谱纯醇为乙醇或异丙醇。
进一步地,色谱柱为硅胶色谱柱、氨基色谱柱或氰基色谱柱,更具体地,色谱柱为99.999%的高纯多孔球形硅胶填装而成的Platisil Silica柱、采用氨基键合技术的Platisil NH2柱、氰丙基二甲基硅烷高密度键合在高纯硅胶基质上的Platisil CN柱,所述色谱柱填料粒径为5um。
进一步地,色谱柱柱温为20-25℃。
进一步地,所述的紫外检测器检测波长为220-260nm。
进一步地,所述流动相流速为0.8-1.2mL/min。
进一步地,溶解试剂为乙醇或异丙醇。
本发明的有益效果是:
本发明提供一种光刻胶树脂单体丙烯酸酯类化合物的HPLC分析方法,可以快捷准确的实现丙烯酸酯类产品定性、定量分析,方法稳定可靠。
本发明相比GC与NMR分析检测方法,HPLC法操作简单、灵敏度高、准确性强。本发明通过控制色谱柱柱温箱温度,使样品在整个分析过程中,处于20-25℃,降低了丙烯酸酯类产品因高温产生的聚合;用色谱醇作为溶剂溶解样品,提高样品的溶解性,样品溶液稳定,产品不易自聚。
本方法操作简单、灵敏度高,样品分析周期为20min,分析时间大大缩短,通过外标法进行定量分析,结果误差小于0.5%,且HPLC仪器设备更普遍,提高了工业生产中丙烯酸酯类产品的分析检测效率及检测准确性。
附图说明
图1为本发明实施例1的2-乙基-2-金刚烷基甲基丙烯酸酯的HPLC图谱;
图2为本发明实施例2的2-乙基-2-金刚烷基丙烯酸酯的HPLC图谱;
图3为本发明实施例3的2-甲基-2-金刚烷基甲基丙烯酸酯的HPLC图谱;
图4为本发明实施例4的2-甲基-2-金刚烷基丙烯酸酯的HPLC图谱;
图5为本发明实施例5的2-金刚烷基甲基丙烯酸酯的HPLC图谱;
图6为本发明实施例6的2-金刚烷基丙烯酸酯的HPLC图谱;
图7为本发明实施例7的2-羰基-四氢呋喃-3-羟基-丙烯酸酯的HPLC图谱;
图8为本发明实施例8的2-羰基-四氢呋喃-3-羟基-甲基丙烯酸酯的HPLC图谱;
图9为本发明实施例9的2-甲基-2-丙烯酸-4-羟基苯基酯的HPLC图谱;
图10为本发明实施例10的4-羟基苯基丙烯酸酯的HPLC图谱。
具体实施方式
本发明提供了一种光刻胶丙烯酸酯类树脂单体的HPLC分析方法,本方法采用正相高效液相色谱—紫外检测器,采用高纯多孔球形硅胶填装而成的Platisil Silica柱、采用独特氨基键合技术的Platisil NH2柱、氰丙基二甲基硅烷高密度键合在高纯硅胶基质上的Platisil CN柱(250mm×4.6mm,5um),采用紫外可见吸收检测器,以不同比例的小极性烷烃-醇为流动相,低温下等度洗脱,使用色谱纯的醇溶剂为稀释剂,本发明中溶解试剂即稀释剂为乙醇或异丙醇。
本发明中,通过所述的色谱条件,可以有效分析丙烯酸酯类产品及其相关杂质,本发明所述测试方法,柱温、流速及流动相的比例,均会对丙烯酸酯及其相关杂质产生影响。通过调节流动相比例,丙烯酸酯类产品保留时间会推迟,产品及其杂质的分离度降低,在本发明所述的流动相的比例、柱温、流速条件下,丙烯酸酯类产品及其杂质分离度均大于1.5,符合要求,检测限浓度为0.3ug/ml,灵敏度高,可用于丙烯酸酯类产品工业化分析检测。
丙烯酰胺类树脂单体结构式如下所示:
R2的代表结构为H原子或甲基。
本发明HPLC法为正相色谱法,以小极性溶剂为流动相或者以不同比例的小极性溶剂-醇为流动相,使用紫外检测器,在特定波长条件220-260nm下,色谱柱柱温为20-25℃,流动相流速为0.8-1.2mL/min的色谱条件下高效、快速对丙烯酸酯类树脂单体进行定性和定量分析。
所述树脂单体丙烯酸酯类化合物为:2-乙基-2-金刚烷基甲基丙烯酸酯、2-乙基-2-金刚烷基丙烯酸酯、2-甲基-2-金刚烷基甲基丙烯酸酯、2-甲基-2-金刚烷基丙烯酸酯、2-金刚烷基甲基丙烯酸酯、2-金刚烷基丙烯酸酯、2-羰基-四氢呋喃-3-羟基-丙烯酸酯、2-羰基-四氢呋喃-3-羟基-甲基丙烯酸酯、2-甲基-2-丙烯酸-4-羟基苯基酯或4-羟基苯基丙烯酸酯。
所述流动相中的小极性溶剂为正己烷或环己烷。
所述流动相中的色谱纯醇为乙醇或异丙醇。
所述流动相为小极性烷烃与色谱纯醇的混合溶液,其中小极性烷烃的体积分数为80-100%,余量为色谱纯醇。
实施例1
仪器与条件
色谱柱:Platisil Silica(250*4.6mm,5.0um);
流动相:正己烷:乙醇90:10等度洗脱;
流速:0.8mL/min;
柱温:20℃;
检测波长:220nm;
稀释剂:异丙醇;
进样量:20uL
实验步骤
称取2-乙基-2-金刚烷基甲基丙烯酸酯产品5mg,置于25mL容量瓶中,用异丙醇溶解并稀释至刻度,摇匀,作为供试品溶液,吸取供试品溶液,注入液相色谱仪器,按上述条件采集图谱,记录色谱图。色谱图见图1。
实施例2
仪器与条件
色谱柱:Platisil Silica(250*4.6mm,5.0um);
流动相:正己烷:乙醇90:10等度洗脱;
流速:1.0mL/min;
柱温:20℃;
检测波长:230nm;
稀释剂:异丙醇;
进样量:20uL
实验步骤
称取2-乙基-2-金刚烷基丙烯酸酯产品5mg,置于25mL容量瓶中,用异丙醇溶解并稀释至刻度,摇匀,作为供试品溶液,吸取供试品溶液,注入液相色谱仪器,按上述条件采集图谱,记录色谱图。色谱图见图2。
实施例3
仪器与条件
色谱柱:Platisil Silica(250*4.6mm,5.0um);
流动相:环己烷:异丙醇80:20等度洗脱;
流速:1.0mL/min;
柱温:22℃;
检测波长:240nm;
稀释剂:乙醇;
进样量:20uL
实验步骤
称取2-甲基-2-金刚烷基甲基丙烯酸酯产品5mg,置于25mL容量瓶中,用乙醇溶解并稀释至刻度,摇匀,作为供试品溶液,吸取供试品溶液,注入液相色谱仪器,按上述条件采集图谱,记录色谱图。色谱图见图3。
实施例4
仪器与条件
色谱柱:Platisil Silica(250*4.6mm,5.0um);
流动相:环己烷等度洗脱;
流速:1.0mL/min;
柱温:22℃;
检测波长:220nm;
稀释剂:乙醇;
进样量:20uL
实验步骤
称取2-甲基-2-金刚烷基丙烯酸酯产品5mg,置于25mL容量瓶中,用乙醇溶解并稀释至刻度,摇匀,作为供试品溶液,吸取供试品溶液,注入液相色谱仪器,按上述条件采集图谱,记录色谱图。色谱图见图4。
实施例5
仪器与条件
色谱柱:Platisil NH2,5um(250*4.6mm);
流动相:正己烷:乙醇80:20等度洗脱;
流速:1.2mL/min;
柱温:25℃;
检测波长:220nm;
稀释剂:异丙醇;
进样量:20uL
实验步骤
称取2-金刚烷基甲基丙烯酸酯产品5mg,置于25mL容量瓶中,用异丙醇溶解并稀释至刻度,摇匀,作为供试品溶液,吸取供试品溶液,注入液相色谱仪器,按上述条件采集图谱,记录色谱图。色谱图见图5。
实施例6
仪器与条件
色谱柱:Platisil NH2,5um(250*4.6mm);
流动相:正己烷:乙醇90:10等度洗脱;
流速:0.8mL/min;
柱温:25℃;
检测波长:230nm;
稀释剂:异丙醇;
进样量:20uL
实验步骤
称取2-金刚烷基丙烯酸酯产品5mg,置于25mL容量瓶中,用异丙醇溶解并稀释至刻度,摇匀,作为供试品溶液,吸取供试品溶液,注入液相色谱仪器,按上述条件采集图谱,记录色谱图。色谱图见图6。
实施例7
仪器与条件
色谱柱:Platisil Silica(250*4.6mm,5.0um);
流动相:正己烷:乙醇80:20等度洗脱;
流速:1.0mL/min;
柱温:20℃;
检测波长:220nm;
稀释剂:异丙醇;
进样量:20uL
实验步骤
称取2-羰基-四氢呋喃-3-羟基-丙烯酸酯产品5mg,置于25mL容量瓶中,用异丙醇溶解并稀释至刻度,摇匀,作为供试品溶液,吸取供试品溶液,注入液相色谱仪器,按上述条件采集图谱,记录色谱图。色谱图见图7。
实施例8
仪器与条件
色谱柱:Platisil Silica(250*4.6mm,5.0um);
流动相:正己烷:乙醇90:10等度洗脱;
流速:0.8mL/min;
柱温:20℃;
检测波长:230nm;
稀释剂:异丙醇;
进样量:20uL
实验步骤
称取2-羰基-四氢呋喃-3-羟基-甲基丙烯酸酯产品5mg,置于25mL容量瓶中,用异丙醇溶解并稀释至刻度,摇匀,作为供试品溶液,吸取供试品溶液,注入液相色谱仪器,按上述条件采集图谱,记录色谱图。色谱图如图8。
实施例9
仪器与条件
色谱柱:Platisil CN(250x4.6mm,5um);
流动相:正己烷:乙醇90:10等度洗脱;
流速:1.0mL/min;
柱温:20℃;
检测波长:254nm;
稀释剂:二氯甲烷;
进样量:20uL
实验步骤
称取2-甲基-2-丙烯酸-4-羟基苯基酯产品5mg,置于25mL容量瓶中,用二氯甲烷溶解并稀释至刻度,摇匀,作为供试品溶液,吸取供试品溶液,注入液相色谱仪器,按上述条件采集图谱,记录色谱图。色谱图见图9。
实施例10
仪器与条件
色谱柱:Platisil CN(250x4.6mm,5um);
流动相:正己烷:乙醇90:10等度洗脱;
流速:1.0mL/min;
柱温:20℃;
检测波长:260nm;
稀释剂:二氯甲烷;
进样量:20uL
实验步骤
称取4-羟基苯基丙烯酸酯产品5mg,置于25mL容量瓶中,用二氯甲烷溶解并稀释至刻度,摇匀,作为供试品溶液,吸取供试品溶液,注入液相色谱仪器,按上述条件采集图谱,记录色谱图。色谱图见图10。
以上所述实施方式为本发明的优选实施例,而非本发明可行实施的穷举。对于本领域的技术人员而言,在不脱离本发明的精神和实质的情况下,做出的各种改进,都应当被认为包含在本发明的保护范围内。
Claims (9)
1.一种光刻胶树脂单体丙烯酸酯类化合物的HPLC分析方法,其特征在于,采用正相高效液相色谱法,流动相为小极性烷烃与色谱纯醇的混合溶液,其中小极性烷烃的体积分数为80-100%,余量为色谱纯醇;使用紫外检测器通过等度洗脱对丙烯酸酯类树脂单体进行分析检测。
2.根据权利要求1所述的一种光刻胶树脂单体丙烯酸酯类化合物的HPLC分析方法,其特征在于,所述树脂单体丙烯酸酯类化合物为:2-乙基-2-金刚烷基甲基丙烯酸酯、2-乙基-2-金刚烷基丙烯酸酯、2-甲基-2-金刚烷基甲基丙烯酸酯、2-甲基-2-金刚烷基丙烯酸酯、2-金刚烷基甲基丙烯酸酯、2-金刚烷基丙烯酸酯、2-羰基-四氢呋喃-3-羟基-丙烯酸酯、2-羰基-四氢呋喃-3-羟基-甲基丙烯酸酯、2-甲基-2-丙烯酸-4-羟基苯基酯或4-羟基苯基丙烯酸酯。
3.根据权利要求1所述的一种光刻胶树脂单体丙烯酸酯类化合物的HPLC分析方法,其特征在于,所述流动相中的小极性烷烃为正己烷或环己烷。
4.根据权利要求1所述的一种光刻胶树脂单体丙烯酸酯类化合物的HPLC分析方法,其特征在于,所述流动相中的色谱纯醇为乙醇或异丙醇。
5.根据权利要求1所述的一种光刻胶树脂单体丙烯酸酯类化合物的HPLC分析方法,其特征在于,色谱柱为硅胶色谱柱、氨基色谱柱或氰基色谱柱,所述色谱柱填料粒径为5um。
6.根据权利要求5所述的一种光刻胶树脂单体丙烯酸酯类化合物的HPLC分析方法,其特征在于,色谱柱柱温为20-25℃。
7.根据权利要求1所述的一种光刻胶树脂单体丙烯酸酯类化合物的HPLC分析方法,其特征在于,所述的紫外检测器检测波长为220-260nm。
8.根据权利要求1所述的一种光刻胶树脂单体丙烯酸酯类化合物的HPLC分析方法,其特征在于,所述流动相流速为0.8-1.2mL/min。
9.根据权利要求1所述的一种光刻胶树脂单体丙烯酸酯类化合物的HPLC分析方法,其特征在于,溶解试剂为乙醇或异丙醇。
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