CN112062774A - 一种有机化合物和使用该化合物的有机电致发光器件 - Google Patents
一种有机化合物和使用该化合物的有机电致发光器件 Download PDFInfo
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- CN112062774A CN112062774A CN202010938193.0A CN202010938193A CN112062774A CN 112062774 A CN112062774 A CN 112062774A CN 202010938193 A CN202010938193 A CN 202010938193A CN 112062774 A CN112062774 A CN 112062774A
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- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
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- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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Abstract
本发明公开了一种应用于有机电致发光领域的一种有机化合物和使用该化合物的有机电致发光器件,该有机化合物的分子结构式为结构式1所示结构:
Description
技术领域
本发明涉及有机电致发光领域的一种有机化合物和使用该化合物的有机电致发光器件,具体为三苯胺衍生物和使用该化合物的有机电致发光器件。
背景技术
有机电致发光器件(OLED:Organic Light Emiss1on Diodes)有视角广阔、响应速度快、色彩质量高、可实现柔性发光等优点,具有广阔的应用前景。OLED器件通常是类三明治结构,包括正负电极膜层及夹在电极膜层之间的有机功能材料层。对OLED器件的电极施加电压,正电荷从正极注入,负电荷从负极注入,在电场作用下正负电荷在有机层中迁移相遇复合发光。已被广泛应用于新型照明灯具、智能手机及平板电脑等产品的显示面板,进一步还将向电视等大尺寸显示产品应用领域扩展,是一种发展快、技术要求高的新型显示技术。
一个效率好寿命长的有机电致发光器件通常是器件结构与各种有机材料的优化搭配的结果。常见的OLED器件通常包括以下种类的有机材料:空穴注入材料、空穴传输材料、电子传输材料,以及各色的发光材料(染料或者掺杂客体材料)和相应的主体材料等。
现在的磷光电致发光器件中大多采用主客体结构,即将磷光发射物质以一定的浓度掺杂在主体物质中,以避免三重态-三重态湮灭,提高磷光发射效率。作为现有的蓝光主体材料是基于蒽的稠环类衍生物,如专利CN1914293B、CN102448945B、 US2015287928A1等所述,然而这些化合物存在发光效率和亮度不充分及器件寿命较差的问题。作为现有技术的发蓝光客体化合物,可采用的是芳基乙烯基胺类化合物(WO 04/013073,WO 04/016575,WO 04/018587)。然而,这些化合物的热稳定性差,易分解,导致器件的寿命差,是目前产业上OLED材料最主要的缺点。此外,这些化合物的色纯度差,难以实现深蓝色的发光。另外,US7233019、KR 2006-0006760等专利公开了利用芳基胺取代基的芘系化合物的有机电致发光元件,但是因为蓝光的色纯度低,很难实现深蓝发光。
在磷光主体材料中,最常使用的是空穴传输型主体材料。这类材料的分子中含有电子给体,如咔唑和三苯胺结构,具有空穴传输的特点。三苯胺具有很高的三线态能级, ET为3.04eV,经常使用空的穴传输材料TAPC、TcTa、TPD等都是三苯胺的衍生物。大多数三苯胺的衍生物的HOMO能级要比咔唑衍生物高,大概为-5.3eV,而且它与 1TO的功函数接近,HOMO也与空穴传输材料NPB接近,有利于空穴的注入,因此它们适合于做电致磷光主体材料。但是由于三苯胺分子结构是扭曲的,缺少刚性,使得三苯胺衍生物的热稳定性和形貌稳定性不够好,这影响了它们的实际应用。所以关于三苯胺衍生物作为磷光主体材料的报道不是很多。为了提高三苯胺的刚性结构,Yang课题组合成了桥联结构的三苯胺衍生物FATPA,[“Afully diarylmethylene-bridged triphenylamine derivative as novel host forhighly efficient green phosphorescent OLEDs”, Org.Lett.2009,11,1503.]它是通过苯胺的邻位与二苯甲烷的亚甲基连接,三苯胺形成了接近平面的环状结构,这样的结构使得分子具有较高的玻璃转化温度,Tg为178℃。该分子同时保持了较高的三线态能级(ET=2.78eV)和HOMO(-5.22eV)能级。
相对于红色磷光材料和绿色磷光材料,蓝色磷光材料是开发得最晚的,也是最不成熟的。这主要是由蓝色磷光波长短能级高,为了获得短波长发光,就必须拉大配体的能隙,即通过修配体的化学结构来拉大配体的HOMO和LUMO的能级,但是,这样又会导致配体和金属之间的配位键的减弱,一方面使得配合物的稳定性降低,配合物容易发生键断裂,而且会加速配合物以非辐射方式衰减会到基态,使磷光效率降低。因此,在蓝色磷光材料中,波长的蓝移和高效发光是一对矛盾,同时兼有两者是两难的选择。同时这也是器件的结构中起发光作用的磷光掺杂材料往往要搭配的主体材料使用的原因,但蓝色磷光材料的三线态能级比较高,所以常常需要比其三线态能级高的主体材料与之相匹配,这样才能保证将能量传递给客体蓝色磷光材料,释放出磷光。如果主体材料的三线态能级低于蓝色磷光材料的三线态能级,则能量会传递到主体材料上释放,而主体材料是纯的有机化合物,在室温下是看不到磷光的,所以器件的发光效率会降低。同时现有的蓝光材料存在热稳定性差,易分解,导致器件的寿命差;色纯度差,难以实现深蓝色的发光,因此在体现天然颜色的全彩色显示器方面有问题。因此,仍需进一步改进材料。高性能的蓝光材料一直是人们的开发重点。
本发明化合物不对称的结构特性提高器件效率,热稳定性、成膜等性能,本专利比较相对合成路线简单。本发明的有机化合物应用于OLED器件中的发光层,并当作蓝光材料使用,本发明化合物三苯胺与芴连接起来三苯胺衍生物,由于螺环上的C原子阻断了三苯胺与其它苯环的共轭,使得分子的三线态得到了维持,具有较高的三线态能级,能量传递更加充分;电子和空穴的传递更加平衡,器件的效率和寿命更高。
发明内容
本发明为解决常用蓝色磷光材料的玻璃化温度较低,材料本身稳定性不高,且在高亮度下具有高效率滚降,阻碍其广泛使用的问题,而提供一种有机化合物、其合成方法及其在有机电致发光领域的应用。该有机化合物的分子结构如结构式1所示:
其中,结构式1中,Ar1至Ar4独立地选自取代或未取代的C6-C60的芳基、取代或未取代的C2-C30的杂芳基,其中杂芳基含有选自B、N、O、S、Si及P中至少一个杂原子。
优先的所述的C6-C30芳基选自苯基、萘基、联苯基、三联苯基和菲基中的一种。
优先的所述的C2-C30杂芳基选自吡啶基、联吡啶基、喹啉基、异喹啉基、菲咯啉基和三嗪基中的一种。
进一步的优选的方式是,所述的有机化合物独立地选自下列化合物:
本发明还提供了一种有机电致发光器件,该器件包括阴极层、阳极层和有机层,该有机层包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子注入层或电子传输层中至少一层,其中有机层中至少有一层含有如结构式1所表示的化合物。
其中,结构式1所表示的一种有机化合物如前所述。
进一步的,结构式1所表示的一种有机化合物作为有机电致发光器件发光层的一种有机材料。
进一步的,结构式1所表示的一种有机化合物作为有机电致发光器件发光层的客体掺杂剂。
进一步的,如结构式1所表示的化合物可以单独使用在有机电致发光器件中,或和其他化合物混合使用;如结构式1所表示的化合物可以使用其中一种化合物,也可以同时使用结构式1中的两种或两种以上化合物;单独使用一种选自结构式1所述的化合物,或同时使用两种以上选自结构式1所述的化合物。
在本发明中,所述发光层可以为红色、黄色或蓝色发光层。在本发明中,所述发光层为蓝色发光层时,采用上述所述的有机电致器件用化合物作为蓝色主体或蓝色掺杂,可得到高效率、高分辨率、高亮度及长寿命的有机电致器件。
在本发明中,所述有机物层优选包括电子传输层,所述电子传输层包括上述技术方案所述的有机电致器件用化合物。在本发明中,所述电子传输层优选还包括金属化合物。
在本发明中,所述有机物层优选包括发光层和电子传输层,所述发光层和电子传输层均含有上述技术方案所述的有机电致器件用化合物,所述发光层和电子传输层中的有机化合物可以相同也可以不同。
本发明对所述有机电致器件的制备方法没有特殊的限制,除了使用式1的有机电致器件用化合物之外,采用本领域技术人员熟知的发光器件的制备方法和材料制备得到即可。
本发明所述的有机电致发光器件是有机光伏器件、有机发光器件(OLED)、有机太阳电池(OSC)、电子纸(e-paper)、有机感光体(OPC)、有机薄膜晶体管(OTFT) 及有机内存器件(Organ1c Memory Element)中任意一种。
在本发明中,有机电致发光器件是可以利用喷溅涂覆法、电子束蒸发、真空蒸镀等方法在基板上蒸镀金属或具有导电性的氧化物以及它们的合金形成阳极;在制备得到的阳极表面按顺序蒸镀空穴注入层、空穴传输层、发光层、空气阻挡层和电子传输层,以后再蒸镀阴极的方法制备。以上方法以外基板上按阴极、有机物层、阳极顺序蒸镀制作有机电致发光器件。所述有机物层是也可以包括空穴注入层、空穴传输层、发光层、空穴阻挡层及电子传输层等多层结构。在本发明中有机物层是采用高分子材料按溶剂工程 (旋转涂膜(sp1n-coat1ng)、薄带成型(tape-cast1ng)、刮片法(doctor-blad1ng)、丝网印刷 (Screen-Pr1nt1ng)、喷墨印刷或热成像(Thermal-1mag1ng)等)替代蒸镀方法制备,可以减少器件层数。
根据本发明的有机电致发光器件所使用的材料可以分为顶发射、低发射或双面发射。根据本发明实施方案的有机电致发光器件的化合物可以有机电致发光器件类似的原理适用于有机太阳能电池、照明的OLED、柔性OLED、有机感光体,有机薄膜晶体管等电致器件方面。
与现有技术相比,本发明的有益效果是:
本发明新型一种有机化合物分子量比较大,通过单键连接的多个共轭平面基团,空间对称性差,不易结晶分解,提高了材料的玻璃化温度,保证了材料长时间蒸镀不被分解;.本发明的有机化合物应用于电致发光器件,具有较大的T1能够阻挡激子扩散,提高器件的效率和寿命;本发明的一种有机磷光化合物能够平衡空穴和电子的传递,提高器件的寿命。
附图说明
图1为本发明的有机电发光二极管发光色度和可见度关系图。
具体实施方式
为了使本发明的目的、技术方案及优点更加清楚明白,以下结合具体实施例,对本发明进行进一步详细说明。应当理解,此处所描述的具体实施例仅仅用以解释本发明,并不用于限定本发明。
中间体L的合成:
1、在2L圆底烧瓶中投入L-4(117.0g,0.283mol)、中间体L-5(60.6g,0.340mmol)、[1,1’-双(二苯基膦)二茂铁]二氯钯(6.94g,0.008mol)、碘化铜(1.62g,0.008mol)、三苯基膦(7.4g,0.028mol)、三乙胺(500mL),并在氮气条件下进行5个小时的回流搅拌。再反应完毕之后冷却至常温,并投入庚烷400mL而使反应结束。过滤以后减压蒸馏得到固体L-3(118.5g,82%)
2、在2L圆底烧瓶中将L-3(118.5g,0.232mol)溶剂投入于二氯甲烷960ml,并在氮气条件下冷却至-78.再冷却溶液中滴加一氯化碘(278ml,0.279mol),并在常温下搅拌了12小时。反应完毕之后,肉肉硫代硫酸钠饱和水溶液并进行了搅拌。利用二氯甲烷和水进行萃取而对有机层进行分离,并进行了减压浓缩。利用甲醇进行重结晶而得到了中间体L-2(90.1g,61%)。
3、在氮气条件下,碳酸铯(390mg,1.2mmol),双(苄腈)二氯钯(9.6mg, 0.025mmol)和三{3,5-双(三氟甲基)苯基}-膦(34mg,0.050mmol)是置于20mL Schlenktube中。加入L-2(318mg,0.50mmol)在甲苯(2.0mL)中的溶液。将所得混合物在110℃下搅拌24h。然后将混合物冷却至室温。加入盐酸(1M,6mL),并用乙酸乙酯(10mL×3)萃取产物。然后将有机层用盐水洗涤,并用无水硫酸钠干燥。蒸发掉挥发物后,以己烷为洗脱液通过硅胶柱纯化,得到L-1(203mg,0.400mmol, 80%产率)。
4、在500mL圆底烧瓶中加入了L-1(7.6g,15mmol)、二氯甲烷180mL并常温搅拌。将溴(1.7mL,33mmol)稀释滴加到二氯甲烷50mL,常温下搅拌8小时,反应完毕后在反应容器中国投入丙酮100mL并搅拌。将生成的固体过滤之后利用丙酮进行清洗。用一氯苯重结晶固体而获得中间体L(7.5g,收率,75%)。质谱m/z,理论值:666.36;实测值: 665.97。
实施例1:化合物C-1的合成
在250mL圆底烧瓶中加入L(7.1g,10.6mmol)、3-甲基二苯胺(4.7g,25.4mol)、 Pd2(dba)3(0.08g,0.4mmol)、叔丁醇钠(3.4g,0.035mol)、三叔丁基膦(0.07g,0.4mmol)、甲苯60mL,并回流搅拌2小时。在反应完毕之后常温冷却。利用二氯甲烷和水对反应溶液进行萃取。分离有机层,并用硫酸镁进行干燥,然后减压浓缩。利用柱层析法对物质进行分离提纯,后利用二氯甲烷和丙酮进行重结晶而获得化合物C-1(7.4g,85%)。质谱m/z,理论值:871.03;实测值:870.32。
实施例2:化合物C-23的制备
将实施例1中的合成方法,得到化合物C-23。质谱m/z,理论值:1039.28;实测值:1038.43。
实施例3:化合物C-29的制备
将实施例1中的合成方法,得到化合物C-29。质谱m/z,理论值:650.72;实测值:650.21。
实施例4:化合物C-38的制备
将实施例1中的合成方法,得到化合物C-38。质谱m/z,理论值:943.02;实测值:942.27。
实施例5:化合物C-41的制备
将实施例1中的合成方法,得到化合物C-41。质谱m/z,理论值:1119.33;实测值:1118.43。
本发明还通过热蒸镀的方式制备了8个底发光器件,各个具体的器件结构如下:
器件实施例:
将费希尔公司涂层厚度为的1TO玻璃基板放在蒸馏水中清洗2次,超声波洗涤30分钟,再用蒸馏水反复清洗2次,超声波洗涤10分钟,蒸馏水清洗结束后,采用异丙醇、丙酮、甲醇溶剂按顺序进行超声波洗涤后干燥,将干燥后的基板转移到等离子体清洗机里,将上述基板洗涤5分钟后送到蒸镀机里。
在已经清洗好的1TO透明电极上依次蒸镀空穴注入层2-TNATA蒸镀厚度为空穴传输层a-NPD蒸镀厚度为ADN(9,10-二(2-萘基)蒽)和5%的BD1~BD3或本发明一种有机化合物蒸镀厚度为空穴阻挡层及电子传输层TPB1蒸镀厚度为L1F蒸镀厚度为和Al蒸镀厚度为形成阴极;上述过程有机物蒸镀速度保持L1F的蒸镀速度为Al的蒸镀速度为
表1为本发明实施例和比较例制备得到的有机发光器件的性能检测结果。
[表1]
从上述表1结果中,采用本发明提供的有机电致发光器件用化合物制备有机电致发光器件,有机电致发光器件的发光效率和寿命特性显著提高。
以上所述,仅为本发明较佳的具体实施方式,但本发明的保护范围并不局限于此,任何熟悉本技术领域的技术人员在本发明揭露的技术范围内,根据本发明的技术方案及其发明构思加以等同替换或改变,都应涵盖在本发明的保护范围之内。
Claims (8)
2.根据权利要求1所述的有机化合物,其特征在于:所述的C6-C30芳基选自苯基、萘基、联苯基、三联苯基和菲基中的一种。
3.根据权利要求1所述的有机化合物,其特征在于:所述的C2-C30杂芳基选自吡啶基、联吡啶基、喹啉基、异喹啉基、菲咯啉基和三嗪基中的一种。
5.一种有机电致发光器件,包括阴极层、阳极层和有机层,该有机层包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子注入层、电子传输层中的至少一层,其特征在于:该器件的有机层中至少有一层含有如权利要求1所述的有机化合物。
6.根据权利要求5所述的有机电致发光器件,其特征在于,有机电致发光器件发光层中含有权利要求1所述的化合物。
7.根据权利要求5或权利要求6所述的有机电致发光器件,其特征在于,权利要求1所述的化合物在有机电致发光器件发光层中作为客体掺杂剂使用。
8.根据权利要求5所述的有机电致发光器件,其特征在于,权利要求1所述的化合物可以单独使用,或和其他化合物混合使用。
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CN111116628A (zh) * | 2019-12-31 | 2020-05-08 | 浙江华显光电科技有限公司 | 一种有机化合物和使用该化合物的有机电致发光器件 |
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