CN112707925A - 一种有机电致发光材料及其应用 - Google Patents
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Abstract
Description
技术领域
本发明涉及一种有机电致发光材料及其应用,属于有机光电材料技术领域。
背景技术
Pope等人于1965年首次发现了单晶蒽的电致发光性质,这是有机化合物的首例电致发光现象,经过多年的不断发展,有机电致发光器件既可以用来制造新型显示产品,也可以用于制作新型照明产品,有望取代现有液晶显示与荧光灯照明。
目前,基于OLED显示技术的商品,已经实现产业化。与液晶类显示技术相比,OLED显示技术具有自发光、无辐射、质量轻、厚度薄、广视角、宽色域、颜色稳定、响应速度快、环境适应强、可实现柔性显示等诸多优点,因此,OLED显示技术正在获得人们越来越多的关注和相应的技术投入。
主客掺杂发光体(host guest doped emitter)系统的发明,是促成OLED显示技术进展的关键之一,因为具有优越电子传输及发光特性的主发光体材料,可以和各种高荧光效率的客发光体结合,得到高发光效率的不同色光。这种发光系统的精髓是,用主、客发光体的分子设计及能阶与界面的搭配,将载子的输送、导电功能与其发光机制分开,并个别的改善而使之最佳化,最终的目的是使OLED发光体能够达到最好的电功能与发光效率。
上述理论的深层机理在于,通常有机分子的结构非常复杂,要使有机分子导电,就必须设计分子为扁平型的高共轭电子分布系统,让分子间有效并且有次序的堆栈,从而在一定的电场下发挥最佳的载子传输与迁移。但是,要使有机分子在固态下发光,最好是分子与分子之间没有相互作用或易堆栈的相关性,因为这会导致能量转换与高浓度下的荧光淬灭。而将高质量比的主发光体材料与一定量的高荧光效率的客发光体材料进行合理搭配,即可以获得理想发光效率的发光层。
9,10-二(2-萘基)蒽,又名AND,是美国柯达公司公布的最早的蓝光主发光体材料,其液态与固态下均有相当好的荧光效率,广泛见诸于相关蓝光器件结构。但其薄膜态相当不稳定且易结晶,且色光略显偏绿(CIEx,y=0.20,0.26),已远远无法满足高世代OLED产线的使用需求。
发明内容
本发明针对现有技术存在的不足,提供一种有机电致发光材料及其应用,所述的有机电致发光材料具有较高的玻璃化温度、合适的HOMO能级与LUMO能级、较宽的能隙、合适的S1能级、薄膜态稳定且不易结晶。
本发明解决上述技术问题的技术方案如下:一种有机电致发光材料,所述有机电致发光材料的结构式由下式(Ⅰ)所示:
其中,X1代表碳原子数量不超过16的四取代的脂肪环及其衍生物的任意一种;X2代表二苯并杂芳环衍生物任意一种。所述的有机电致发光材料具有电致发光性能,可以作为有机电致发光器件的功能层材料,应用在有机电致发光领域中。
在上述技术方案的基础上,本发明还可以做如下改进。
进一步的,所述X1选自以下基团中的任意一种:
采用上述进一步方案的有益效果是:得到了更合适的分子大小、非平面的空间立体结构以及合适的分子能级分布。
进一步的,所述X2选自以下基团中的任意一种:
采用上述进一步方案的有益效果是:得到了更合适的分子大小、非平面的空间立体结构以及合适的分子能级分布。
进一步的,所述式(Ⅰ)所示的化合物,具体为下述C01-C21中的任意一种:
采用上述进一步方案的有益效果是:经过分子模拟计算HOMO与LUMO能级、S1能级,可以搭配现有商业成品材料,并且它们通过后期器件评价试验,确认了优良的光电性能。
本发明还公开了所述有机电致发光材料的应用:
所述的有机电致发光材料应用于有机电致发光器件种的至少一个功能层。
进一步的,所述的有机电致发光器件包括阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层及阴极;其中,在所述阳极上依次叠置所述空穴注入层、空穴传输层、发光层、电子传输层、电子注入层和阴极。
进一步的,所述的有机电致发光材料应用于所述的发光层中,所述的有机电致发光材料作为蓝光荧光主体材料应用于发光层中。
本发明的有益效果是:
1)通过常规的有机合成方法,构建了一类以脂肪环酰亚胺为核心结构的化合物分子,均为未见报道的原创结构;
2)所述有机电致发光材料的结构具有合适的分子共轭长度、高度的非平面结构特点,以及适当的分子质量(分子量可达700-1200),使其具有良好的薄膜稳定性(不易结晶)、适合的分子能级(可搭配现有各功能层材料);
3)所述有机电致发光材料非常适合作为小分子OLED器件的发光层,应用于有机电致发光领域中,以该类材料作为发光层,制作的OLED器件,器件的最大亮度4650-6440cd/m2,最大电流效率2.0-3.2cd/A,器件效率良好;
4)所述有机电致发光材料具有较好的蓝光荧光主体材料的发光性能,整体性能明显优于商品化材料ADN,同样的器件设计,本发明中化合物的启亮电压更低,最大电流效率更高,说明本发明所涉及这类材料具有商业化潜力和进一步开发的前景。
附图说明
图1为实施例中所述有机电致发光器件的结构示意图;
图2为实施例中所述化合物C01的核磁氢谱谱图;
图3为实施例中所述化合物C01的质谱谱图;
图中,1阳极,2空穴注入层,3空穴传输层,4发光层,5电子传输层,6电子注入层,7阴极。
具体实施方式
为使本发明的上述目的、特征和优点能够更加明显易懂,下面对本发明的具体实施方式做详细的说明。在下面的描述中阐述了很多具体细节以便于充分理解本发明。但是本发明能够以很多不同于在此描述的其它方式来实施,本领域技术人员可以在不违背本发明内涵的情况下做类似改进,因此本发明不受下面公开的具体实施例的限制。
除非另有定义,本文所使用的所有的技术和科学术语与属于本发明的技术领域的技术人员通常理解的含义相同。本文中在本发明的说明书中所使用的术语只是为了描述具体的实施方式的目的,不是旨在于限制本发明。
化合物制备实施例:
实施例1化合物C01的制备
在250mL三口瓶中,加入CBDA(3.9g,0.02mol),硼胺中间体A(15.9g,0.04mol),丙酸(120g),体系在氮气保护下,缓慢升温至100~120℃。保温反应24h后,反应体系析出类白色固体粉末。体系降至室温,抽滤,得白色滤饼。使用100g四氢呋喃加热溶解滤饼,所得溶液快速过15cm厚的硅胶柱,过柱液脱溶剂得白色固体粗品,粗品使用甲苯:石油醚=1:2重结晶纯化,冷却后抽滤并干燥,得到化合物C01,白色固体14.7g,收率77.0%。
质谱,APCI源,负离子模式,分子式C62H64B2N2O6,理论值954.50,测试值953.33。元素分析(C62H64B2N2O6),理论值C:77.99,H:6.76,O:10.06,实测值C:77.92,H:6.81,O:10.09。
实施例2化合物C02的制备
按照实施例1所述方法(化合物C01的制备),投入硼胺中间体B(12.5g,0.04mol),代替硼胺中间体A(15.9g,0.04mol),得到化合物C02,白色固体10.0g,收率63.6%。
质谱,APCI源,负离子模式,分子式C50H40B2N2O6,理论值786.31,测试值785.18。元素分析(C50H40B2N2O6),理论值C:76.36,H:5.13,O:12.20,实测值C:76.31,H:5.18,O:12.22。
实施例3化合物C07的制备
按照实施例1所述方法(化合物C01的制备),投入DMCBDA(4.5g,0.02mol),代替CBDA(3.9g,0.02mol),得到化合物C07,白色固体15.7g,收率79.9%。
质谱,APCI源,负离子模式,分子式C64H68B2N2O6,理论值982.53,测试值981.44。元素分析(C64H68B2N2O6),理论值C:78.21,H:6.97,O:9.77,实测值C:78.27,H:6.91,O:9.72。
实施例4化合物C08的制备
按照实施例3所述方法(化合物C07的制备),投入氮胺中间体A(12.7g,0.04mol),代替硼胺中间体A(15.9g,0.04mol),得到化合物C08,白色固体9.1g,收率55.4%。
质谱,APCI源,负离子模式,分子式C52H44N4O6,理论值820.33,测试值819.27。元素分析(C52H44N4O6),理论值C:76.08,H:5.40,O:11.69,实测值C:76.04,H:5.42,O:11.71。
实施例5化合物C10的制备
按照实施例3所述方法(化合物C07的制备),投入硼胺中间体C(12.0g,0.04mol),代替硼胺中间体A(15.9g,0.04mol),得到化合物C10,白色固体9.4g,收率59.8%。
质谱,APCI源,负离子模式,分子式C50H40B2N2O6,理论值786.31,测试值785.10。元素分析(C50H40B2N2O6),理论值C:76.36,H:5.13,O:12.20,实测值C:76.40,H:5.10,O:12.24。
实施例6化合物C13的制备
按照实施例1所述方法(化合物C01的制备),投入HPMDA(4.5g,0.02mol),代替CBDA(3.9g,0.02mol),得到化合物C13,白色固体14.1g,收率71.7%。
质谱,APCI源,负离子模式,分子式C64H68B2N2O6,理论值982.53,测试值981.37。元素分析(C64H68B2N2O6),理论值C:78.21,H:6.97,O:9.77,实测值C:78.25,H:6.90,O:9.79。
实施例7化合物C16的制备
按照实施例1所述方法(化合物C01的制备),投入BVDA(5.0g,0.02mol),代替CBDA(3.9g,0.02mol),得到化合物C16,白色固体15.3g,收率76.0%。
质谱,APCI源,负离子模式,分子式C66H68B2N2O6,理论值1006.53,测试值1005.27。元素分析(C66H68B2N2O6),理论值C:78.73,H:6.81,O:9.53,实测值C:78.68,H:6.86,O:9.56。
实施例8化合物C21的制备
按照实施例7所述方法(化合物C16的制备),投入硼胺中间体D(13.7g,0.04mol),代替硼胺中间体A(15.9g,0.04mol),得到化合物C21,白色固体8.2g,收率45.6%。
质谱,APCI源,负离子模式,分子式C60H42B4N2O4,理论值898.35,测试值897.16。元素分析(C60H42B4N2O4),理论值C:80.23,H:4.71,O:7.12,实测值C:80.19,H:4.74,O:7.13。
有机电致发光器件实施例:
本发明选取化合物C01、化合物C02、化合物C07、化合物C08、化合物C10、化合物C13、化合物C16、化合物C21作为发光层材料,制作有机电致发光器件,应当理解,器件实施过程与结果,只是为了更好地解释本发明,并非对本发明的限制。
器件实施例1化合物C01在有机电致发光器件中的应用
本实施例按照下述方法制备有机电致发光器件一:
a)清洗ITO(氧化铟锡)玻璃:分别用去离子水、丙酮、乙醇超声清洗ITO玻璃各30分钟,然后在等离子体清洗器中处理15分钟;
b)在阳极1ITO玻璃上真空蒸镀空穴注入层2HAT-CN,厚度为25nm;
c)在空穴注入层2上真空蒸镀空穴传输层3NPB,厚度为40nm;
d)在空穴传输层3NPB之上,真空混合蒸镀发光层化合物4C01:TBP=9:1(W/W),厚度为35nm;
e)在发光层4之上,真空蒸镀电子传输层5TPBI,厚度为50nm;
f)在电子传输层5之上,真空蒸镀电子注入层6LiF,厚度为1nm;
g)在电子注入层6之上,真空蒸镀阴极7Al,厚度为120nm。
器件一的结构为ITO/HAT-CN(25nm)/NPB(40nm)/化合物C01:TBP=9:1(W/W)(35nm)/TPBI(50nm)/LiF(1nm)/Al(120nm),真空蒸镀过程中,压力<1.0×10-3Pa,器件一的启亮电压、最大电流效率、色纯度等光电数据列于后文表1中。
器件实施例2-器件实施例8化合物C07-化合物C21在有机电致发光器件中的应用
分别以化合物C02、化合物C07、化合物C08、化合物C10、化合物C13、化合物C16、化合物C21代替化合物C01,按照器件实施例1所述方法,制作有机电致发光器件二至器件八,器件二至器件八的结构,分别为ITO/HAT-CN(25nm)/NPB(40nm)/(化合物C02-化合物C21):TBP=9:1(W/W)(35nm)/TPBI(50nm)/LiF(1nm)/Al(120nm),器件二至器件六的启亮电压、最大电流效率、色纯度等光电数据如下表1所示。
对比实施例1对比材料ADN在有机电致发光器件中的应用
以商品化主体材料ADN代替化合物C01,按照器件实施例1所述方法,制作有机电致发光器件九,其结构为ITO/HAT-CN(25nm)/NPB(40nm)/ADN:TBP=9:1(W/W)(35nm)/TPBI(50nm)/LiF(1nm)/Al(120nm),器件九的启亮电压、最大电流效率、色纯度等光电数据如下表1所示。
其中的穴注入层HAT-CN、空穴传输层NPB、电子传输层TPBI、发光层材料TBP与ADN具体结构如下:
表1器件一至器件七的光电数据表
本发明所涉及该类材料具有较好的发光性能,通过器件结构优化,可显著提升有机电致发光器件的光电性能及其寿命,具有商业化潜力和进一步开发的前景。
以上所述实施例的各技术特征可以进行任意的组合,为使描述简洁,未对上述实施例中的各个技术特征所有可能的组合都进行描述,然而,只要这些技术特征的组合不存在矛盾,都应当认为是本说明书记载的范围。
以上所述实施例仅表达了本发明的几种实施方式,其描述较为具体和详细,但并不能因此而理解为对发明专利范围的限制。应当指出的是,对于本领域的普通技术人员来说,在不脱离本发明构思的前提下,还可以做出若干变形和改进,这些都属于本发明的保护范围。因此,本发明专利的保护范围应以所附权利要求为准。
Claims (7)
5.一种根据权利要求1-4任意一项所述的一种有机电致发光材料的应用,其特征在于,所述的有机电致发光材料应用于有机电致发光器件种的至少一个功能层。
6.根据权利要求5所述的一种有机电致发光材料的应用,其特征在于,所述的有机电致发光器件包括阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层及阴极;其中,在所述阳极上依次叠置所述空穴注入层、空穴传输层、发光层、电子传输层、电子注入层和阴极。
7.根据权利要求6所述的一种有机电致发光材料的应用,其特征在于,所述的有机电致发光材料应用于所述的发光层中,所述的有机电致发光材料作为蓝光荧光主体材料应用于发光层中。
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