CN113248652B - 一种用于密封有机发光器件的光固化性组合物 - Google Patents
一种用于密封有机发光器件的光固化性组合物 Download PDFInfo
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- CN113248652B CN113248652B CN202011253169.XA CN202011253169A CN113248652B CN 113248652 B CN113248652 B CN 113248652B CN 202011253169 A CN202011253169 A CN 202011253169A CN 113248652 B CN113248652 B CN 113248652B
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- 239000000178 monomer Substances 0.000 claims description 22
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- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 13
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- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
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- ZNXDCSVNCSSUNB-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)CCOCC1CO1 ZNXDCSVNCSSUNB-UHFFFAOYSA-N 0.000 description 1
- DBUFXGVMAMMWSD-UHFFFAOYSA-N trimethoxy-[3-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(CCC[Si](OC)(OC)OC)CCC2OC21 DBUFXGVMAMMWSD-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
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Abstract
本发明涉及一种有机发光器件密封用光固化性组合物,具体来说,包含非硅氧烷基的二甲基丙烯酸酯,含氟基的二甲基丙烯酸酯,甲基丙烯酸酯和引发剂的密封用光固化性组合物。本发明提供耐等离子体特性优良,固化收缩率低,耐久性强的密封用光固化性组合物。另外,本发明可以提供具有防潮和防氧性能优良,可稳定地用于有机发光电子元件密封材料的密封用光固化性组合物。
Description
技术领域
本发明涉及有机发光器件密封用光固化性组合物,尤其涉及包含非硅系二甲基丙烯酸酯,硅系二甲基丙烯酸酯,甲基丙烯酸酯及引发剂在内的密封用光固化性组合物。
背景技术
有机发光器件标识装置是利用电致发光现象自行发光的标识装置,包括有机发光器件。当接触到外界水汽及/或氧气时,有机发光器件的发光特性会降低。因此,需要使用密封组合物将其密封。有机发光器件密封时通常使用由无机封装层、有机封装层依次叠加组成的密封组合物。在这种情况下,有机封装层可能会在等离子体沉淀形成无机封装层的过程中被蚀刻,从而导致其封装性能受到影响,继而损害有机发光器件的发光特性和耐久度。
因此,有必要开发一种具有优异的耐等离子体性,低固化收缩率以及优异的耐久性和耐候性的密封用光固化性组合物的相关技术。
发明内容
本发明旨在解决上述技术问题,提供具有优良的耐等离子体性、低固化收缩率并具有良好的耐久性及耐候性的光固化性组合物。
本发明的另一个目的是提供具有良好的防潮和防氧性能,可稳定地用于电子元件有机膜的光固化性组合物。
本发明的另一个目的是提供一种有机发光器件的密封用组合物。该组合物使用易于通过气相沉积或喷墨法制备有机封装层。
本发明的有益效果:
本发明提供具有优异的耐等离子体性,低固化收缩率以及优异的耐久性和耐候性的密封用光固化性组合物。
另外,本发明可以提供具有防潮和防氧性能优良,可稳定地用于电子元件密封材料的密封用光固化性组合物。
具体实施方式
以下结合具体实施例,对本发明作出进一步详细说明。应当理解,本发明所使用的术语、实施例等仅仅用于解释本发明,并帮助普通技术人员理解,并不用于限定本发明。
除非另外定义,否则本发明中使用的技术术语和科学术语表示本领域普通技术人员通常理解的含义。
本发明涉及用于密封用光固化性组合物,其包含非硅氧烷基的二甲基丙烯酸酯,硅氧烷基的二甲基丙烯酸酯,甲基丙烯酸酯和引发剂。
上述密封用光固化性组合物的特征是:含有10~70%重量比的非硅氧烷基的二甲基丙烯酸酯,10~70%的硅氧烷基的二甲基丙烯酸酯,5~40%的甲基丙烯酸酯及1~10%的引发剂。
上述非硅氧烷基的二甲基丙烯酸酯可提高组合物的耐久性并改善固化收缩率。
上述非硅氧烷二甲基丙烯酸酯为不包含硅氧烷且具有两个甲基丙烯酸酯基的光固化性单体。
上述非硅氧烷二甲基丙烯酸酯可以是具有取代或未取代的C1~C20亚烷基的二甲基丙烯酸酯。
例如,甲二醇二(甲基)丙烯酸酯,乙二醛二甲基丙烯酸酯,丙二醇二甲基丙烯酸酯,丁二醇二甲基丙烯酸酯,戊二醇二甲基丙烯酸酯,己二醇二甲基丙烯酸酯,庚二醇二甲基丙烯酸酯,辛二醇二甲基丙烯酸酯,壬二醇二甲基丙烯酸酯,癸二醇二甲基丙烯酸酯,十一烷二醇二甲基丙烯酸酯,十二烷二醇二甲基丙烯酸酯中的一种或多种。
上述非硅氧烷类二甲基丙烯酸酯的使用量以10~70%质量比为最优,当含量小于10%时,耐久性降低,而当其超过70%时,加工性降低。
上述硅氧烷类二甲基丙烯酸酯可用下列化学式1表示。
(R1,R2为以单键连接且各自独立地选自C1~C5的烷基,X1,X2,X3,X4各自独立选自氢,C1 C3的烷基或氟化烷基,R3,R4独立选自氢或甲基)
化学式2至5为化学式1所表示化合物的具体实例。
上述硅氧烷类二甲基丙烯酸酯的使用量以10~70%重量比为最优,当含量小于10%时,耐久性和固化收缩性降低,而当其超过70%时,加工性降低。
上述单甲基丙烯酸酯的作用是调节组合物的粘度,降低其固化收缩率。
上述单甲基丙烯酸酯是甲基丙烯酸甲酯,甲基丙烯酸乙酯,甲基丙烯酸丁酯,甲基丙烯酸己酯,甲基丙烯酸辛酯,甲基丙烯酸壬酯,甲基丙烯酸癸酯,甲基丙烯酸十二烷基酯,甲基丙烯酸月桂酯,甲基丙烯酸十六烷基酯,甲基丙烯酸2-苯氧基乙基酯,甲基2-苯基苯氧基乙基丙烯酸酯,甲基丙烯酸苯氧基苄酯,甲基丙烯酸苯氧基酯,甲基丙烯酸苯氧基酯,甲基丙烯酸2-乙基苯氧基酯,甲基丙烯酸苄基酯,甲基丙烯酸2-苯乙酯甲基丙烯酸酯,甲基丙烯酸3-苯丙酯,甲基丙烯酸4-苯基丁酯,甲基丙烯酸2-(2-甲基苯基)乙酯,甲基丙烯酸2-(3-甲基苯基)乙酯,甲基丙烯酸2-(4-甲基苯基)乙酯比率,甲基丙烯酸2-(4-丙基苯基)乙酯,甲基丙烯酸2-(4-(1-甲基乙基)苯基)乙酯,2-(4-甲氧基苯基)乙基丙烯酸酯,甲基丙烯酸2-(4-环己基苯基)乙酯,甲基丙烯酸2-(2-氯苯基)乙酯,甲基丙烯酸2-(3-氯苯基)乙酯,甲基丙烯酸2-(4-氯苯基)乙酯,甲基丙烯酸2-(4-溴苯基)乙酯等中的至少一种。
上述单甲基丙烯酸酯的使用量以5~40%重量比为最优,当含量小于5%时,耐久性降低,而当其超过40%时,加工性降低。
上述引发剂,可以使用磷,苯乙酮,三嗪,二苯甲酮,噻吨酮,安息香,肟等。
磷引发剂可使用二苯基(2,4,6-三甲基苯甲酰基)氧化膦,苄基(二苯基)氧化膦,双(2,6-二甲氧基苯甲酰基)(2,4,4-三甲基戊基)氧化膦或者它们的混合物。
引发剂的含量以1~10%重量比为最优,当含量不足1%时,添加的效果不明显,而当其含量超过10%重量比时,组合物的耐久性降低。
另外,该组合物也包含含丙烯酸酯基的硅烷偶联剂。硅烷偶联剂可以通过提高组合物的结合强度来提高有机层的耐久性。
含丙烯酸酯基的硅烷偶联剂为3-甲基丙烯酰氧基丙基甲基二甲氧基硅烷,3-甲基丙烯酰氧基丙基三甲氧基硅烷,3-甲基丙烯酰氧基丙基甲基二乙氧基硅烷,3-甲基丙烯酰氧基丙基三氧基硅烷。乙氧基硅烷,3-丙烯酰氧基丙基三甲氧基硅烷,甲基丙烯酰氧基甲基三乙氧基硅烷和甲基丙烯酰氧基甲基三甲氧基硅烷等。
硅烷偶联剂的含量以2~10%重量比为最优,当含量不足2%时,添加的效果不明显,而当其含量超过10%重量比时,固化收缩率降低。
上述密封用组合物也包含硅烷偶联剂的低聚物。
硅烷偶联剂低聚物用于改善有机膜的粘附性和耐久性,并且可以通过使含环氧基的硅烷偶联剂和含丙烯酸酯基的硅烷偶联剂反应来制备。
含环氧基的硅烷偶联剂包括2-环氧丙氧基乙基甲基二甲氧基硅烷,2-环氧丙氧基乙基甲基二乙氧基硅烷,3-环氧丙氧基丙基甲基二甲氧基硅烷和3-环氧丙氧基丙基甲基二乙氧基硅烷,2-环氧丙氧基乙基三甲氧基硅烷,2-环氧丙氧基乙基三乙氧基硅烷,3-环氧丙氧基丙基三甲氧基硅烷,3-环氧丙氧基丙基三乙氧基硅烷,2-(3,4-环氧环己基)乙基甲基二甲氧基硅烷,2-(3,4-环氧环己基)乙基甲基二乙氧基硅烷,3-(3,4-环氧环己基)丙基甲基二甲氧基硅烷,3-(3,4-环氧环己基)丙基甲基二乙氧基硅烷,2-(3,4-环氧环己基)乙基三甲氧基硅烷,2-(3,4-环氧环己基)乙基三乙氧基硅烷,3-(3,4-环氧环己基)丙基三甲氧基硅烷,3-(3,4-环氧环己基)丙基三乙氧基硅烷等。
上述含丙烯酸酯基的硅烷偶联剂包括3-甲基丙烯酰氧基丙基甲基二甲氧基硅烷,3-甲基丙烯酰氧基丙基三甲氧基硅烷,3-甲基丙烯酰氧基丙基甲基二乙氧基硅烷,3-甲基丙烯酰氧基丙基三氧基硅烷。乙氧基硅烷,3-丙烯酰氧基丙基三甲氧基硅烷,甲基丙烯酰氧基甲基三乙氧基硅烷和甲基丙烯酰氧基甲基三甲氧基硅烷。
硅烷偶联剂低聚物的重均分子量以1,000~10,000g/mol为最优。
硅烷偶联剂低聚物的含量以2~10%重量比为最优。当含量不足2%时,添加效果不显著,超过10%时,耐久性降低。
上述密封用组合物也包含2~10%重量比的含丙烯酸酯基的硅烷偶联剂和丙烯酸单体的共聚物。
共聚物中包含的多个羧基可以改善组合物的结合强度。
上述含丙烯酸酯基的硅烷偶联剂包括3-甲基丙烯酰氧基丙基甲基二甲氧基硅烷,3-甲基丙烯酰氧基丙基三甲氧基硅烷,3-甲基丙烯酰氧基丙基甲基二乙氧基硅烷,3-甲基丙烯酰氧基丙基三乙氧基硅烷,3-丙烯酰氧基丙基三甲氧基硅烷,甲基丙烯酰氧基甲基三乙氧基硅烷和甲基丙烯酰氧基甲基三甲氧基硅烷等。
上述丙烯酸单体包括丙烯酸,甲基丙烯酸,甲基丙烯酸,乙基丙烯酸,丁基丙烯酸,2-乙基己基丙烯酸,癸基丙烯酸,甲基甲基丙烯酸,甲基丙烯酸乙酯,甲基丙烯酸丁酯,2-乙基己基甲基丙烯酸,甲基丙烯酸癸酯等。
上述含丙烯酸酯基的硅烷偶联剂和丙烯酸单体的重量比以10~30:70~90为最佳,不足10:90时粘合强度降低,超过30:70时,耐久性降低。
上述含丙烯酸酯基的硅烷偶联剂和丙烯酸单体的共聚物的含量以2~10%重量比为最佳,不足2%时添加效果不明显,超过10%时耐久性降低。
另外,上述组合物也包含含有羧基的不饱和单体和含有环氧基的不饱和单体的共聚物。
含有羧基的不饱和单体包括含有羧基的乙烯基芳香族单体,含羧基的丙烯酸酯单体,含羧基的氰化乙烯基单体和含羧基的基于乙烯基卤素的单体等。
含有环氧基的不饱和单体包括含环氧基的乙烯基芳香族单体,含环氧基的丙烯酸酯单体,含环氧基的基于乙烯基氰化物的单体和含环氧基的乙烯基卤素类单体等。
上述含有羧基的不饱和单体和含有环氧基的不饱和单体的重量比以70~90:10~30为最佳。
含有羧基的不饱和单体与含有环氧基的不饱和单体的共聚物的含量以1~5%重量比为最佳。不足1%时,添加效果不显著,超过5%时,耐久性降低。
另外,该组合物还包含聚酯多元醇。聚酯多元醇分子中含有大量羟基,因而可以提高组合物的结合强度。可以通过使甘醇成分(如乙二醇,丙二醇,丁二醇,3-甲基戊二醇,己二醇和双氧甲基环己烷)与酸成分(如己二酸,对苯二甲酸和间苯二甲酸)聚合来制备。
聚酯多元醇的重均分子量以1000~10000g/mol为最佳。
聚酯多元醇的含量以1~5%重量比为最佳,不足1%时添加效果不明显,超过5%时耐久性和可加工性降低。
上述组合物还包含热稳定剂,例如酚醛,醌,胺和亚磷酸酯等。
热稳定剂的含量以0.1~5%重量比为最佳,在上述范围内固化收缩率和耐久性为最优。
另外,本发明还涉及一种使用将上述密封用光固化性组合物进行光固化制备的有机膜。
密封用光固化性组合物在25℃下的粘度为5~200cPs时,其加工性和耐久性最佳。
将上述密封用光固化性组合物以0.1~20μm的厚度涂膜后,以10~500mW/cm2照射1~100s可使其光固化。
上述有机膜具有优异的防潮和防氧性能,可以稳定地用作密封电子元件(有机发光元件,照明设备,显示器,传感器,激光器,变色元件,太阳能电池,二极管等)的材料。
以下结合实施例和比较例,对本发明进行进一步详细说明。下列实施例仅为本发明的实施而示例,并不用于限定本发明。
实施例1
将50%重量比的1,10-癸二醇二甲基丙烯酸酯,30%重量比的化学式2化合物,17%重量比的甲基丙烯酸十二烷基酯,2.8%重量比的二苯基(2,4,6-三甲基苯甲酰基)氧化膦和0.2%重量比的季戊四醇四(3-(3,5-二叔丁基-4-羟苯基))丙酸酯混合以制备密封用光固化性组合物。
实施例2
将65%重量比的1,10-癸二醇二甲基丙烯酸酯,5%重量比的化学式2化合物,27%重量比的甲基丙烯酸十二烷基酯,2.8%重量比的二苯基(2,4,6-三甲基苯甲酰基)氧化膦和0.2%重量比的季戊四醇四(3-(3,5-二叔丁基-4-羟基苯基))丙酸酯混合以制备密封用光固化性组合物。
实施例3
将15%重量比的1,10-癸二醇二甲基丙烯酸酯,75%重量比的化学式2化合物,7%重量比的甲基丙烯酸十二烷基酯,2.8%重量比的二苯基(2,4,6-三甲基苯甲酰基)氧化膦和0.2%重量比的季戊四醇四(3-(3,5-二叔丁基-4-羟基苯基))丙酸酯混合以制备密封用光固化性组合物。
实施例4
将50%重量比的1,10-癸二醇二甲基丙烯酸酯,25%重量比的化学式2化合物,17%重量比的甲基丙烯酸十二烷基酯,5%重量比的3-甲基丙烯酰氧基丙基三甲氧基硅烷,2.8%重量比的二苯基(2,4,6-三甲基苯甲酰基)氧化膦和0.2%重量比的季戊四醇四(3-(3,5-二叔丁基-4-羟基苯基))丙酸酯混合以制备密封用光固化性组合物。
实施例5
将70%重量比的3-环氧丙氧基丙基三甲氧基硅烷与30%重量比的3-甲基丙烯酰氧基丙基三甲氧基硅烷混合反应制备硅烷偶联剂低聚物。
将50%重量比的1,10-癸二醇二甲基丙烯酸酯,25%重量比的化学式2化合物,17%重量比的甲基丙烯酸十二烷基酯,5%重量比的硅烷偶联剂低聚物,2.8%重量比的二苯基(2,4,6-三甲基苯甲酰基)氧化膦和0.2%重量比的季戊四醇四(3-(3,5-二叔丁基-4-羟基苯基))丙酸酯混合以制备密封用光固化性组合物。
实施例6
首先制备3-甲基丙烯酰氧基丙基三甲氧基硅烷和丙烯酸的共聚物。
将50%重量比的1,10-癸二醇二甲基丙烯酸酯,25%重量比的化学式2化合物,17%重量比的甲基丙烯酸十二烷基酯,5%重量比的共聚物,2.8%重量比的二苯基(2,4,6-三甲基苯甲酰基)氧化膦和0.2%重量比的季戊四醇四(3-(3,5-二叔丁基-4-羟基苯基))丙酸酯混合以制备密封用光固化性组合物。
比较例1
按照实施例1制备密封用光固化性组合物,但不添加化学式2化合物。
将上述实施例和比较例中制造的密封用光固化性组合物进行光固化处理后合成有机膜,对其特性进行评价,结果见表1。
根据KS K ISO 3759测定尺寸变化率。
根据KS M ISO 1514测定耐水性,干燥72小时后,将样品浸水放置24小时,取出,室温干燥2小时后,观察涂膜的状态,用优,良,中,差四个等级标记涂膜的状态。
通过使用固体比重计测量光固化前液体的比重和光固化后固体的比重来计算固化收缩率(%)。
根据JIS K 5600-5-6测定附着力,用优,良,中,差四个等级来标记。
表1
从表1的数据可以看出,实施例1~6的密封用光固化组合物均表现出较好的尺寸表化率,耐水性,固化收缩率和附着力,其中实施例4~6的性能最优,而比较例的性能则相对较差。
Claims (9)
3.根据权利要求1所述的密封用光固化性组合物,其特征在于:它还包含2~10%重量比的含丙烯酸酯基的硅烷偶联剂。
4.根据权利要求3所述的密封用光固化性组合物,其特征在于:它还包含2~10%重量比的硅烷偶联剂低聚物。
5.根据权利要求4所述的密封用光固化性组合物,其特征在于:它还包含2~10%重量比的含丙烯酸酯基的硅烷偶联剂与丙烯酸单体的共聚物。
6.根据权利要求1所述的密封用光固化性组合物,其中(C)甲基丙烯酸酯是非硅氧烷单甲基丙烯酸酯。
7.根据权利要求1所述的密封用光固化性组合物,其特征在于:它还包含热稳定剂。
8.根据权利要求7所述的密封用光固化性用组合物,上述热稳定剂的含量相对于(A),(B),(C),(D)的总和,为0.01至2000ppm。
9.根据权利要求1所述的密封用光固化性组合物在25℃±2℃下粘度为5至50cps。
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