CN109251152B - 一种有机电致发光材料的制备及应用 - Google Patents
一种有机电致发光材料的制备及应用 Download PDFInfo
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- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 1
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
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Abstract
本发明涉及一种有机电致发光材料的制备及应用，这种发光材料可以有效的实现红光发射，属于无机化学的配位化学领域。单体分子式为：C72H90N4O4Pt2，分子量为：1465.70；Pt2L1为3，3′，4，4′‑联苯四胺缩3，5‑二叔丁基水杨醛铂配合物。本发明设计的新型发光材料，最大紫外吸收波长为564nm，最大磷光发射波长为647nm，分解温度为390℃。将Pt2L1作为发光材料制备成有机电致发光二极管，取得了最大电流效率，流明效率，和亮度分别为：1.39cd·A‑1，0.74lm·W‑1和1774cd·m‑2。该材料所采用的制备方法反应操作简单，条件温和，能够作为光电材料应用在电致发光领域。
Description
技术领域
本发明涉及一种有机电致发光材料，具体涉及一种希夫碱铂配合物的有机电致发光材料及其应用。
背景技术
OLEDs的研究始于20世纪60年代，1963年美国纽约大学的Pope教授第一次发现有机材料单晶蒽的电致发光现象。1987年美国Kodak公司的Tang采用超薄膜技术和新型器件结构制成了工作电压低、发光亮度高的有机电致发光器件，使有机电致发光材料的研究产生根本性变革。随后，在1990年，英国剑桥大学Cavendish实验室的Burroughes教授和Friend教授等人以聚对苯乙烯(PPV)为发光材料，制成了聚合物电致发光器件，开辟了聚合物薄膜电致发光器件领域。1997年，美国普林斯顿大学的Forrest教授发现了电致磷光现象。Forrest教授报道的电致磷光(Phosphorescent Organic Light-emitting Devices，PHOLEDs)技术突破了有机电致荧光材料量子效率低于25％的限制。根据量子力学自旋统计理论，形成单线态激子和三线态激子的概率分别为25％、75％。由于自旋禁阻作用，在通常情况下，三线态的磷光发射非常弱，难以测量。然而，在磷光材料中，配合物中由于重金属原子(Ir,Pt,Os,Au,Cu)的引入，提高了自旋和轨道的耦合，缩短了磷光的寿命，使原有的三线态具有了某些单线态的特性，增强了系间窜越能力，导致禁阻的三线态向基态跃迁变为局部允许，从而使磷光得以顺利发射。从原理上，磷光材料可以利用所有的电子和空穴复合能量发光，且器件的内量子效率可以达到100％，因此引起了广泛关注。
近年来铂配合物作为磷光发光材料吸引了光电科学家的研究兴趣。如本课题组在《J.Mater.Chem.》报道了一系列Schiff碱铂配合物，这些配合物具有体积较大的取代基(如叔丁基、三苯胺等)，可以有效地降低铂配合物分子之间的聚集或激态二聚体的形成，减慢器件效率随电流的滑落(roll-off)，从而极大地提高器件效率。然而，铂配合物相比于铱配合物在PHOLEDs上的报道比较少，总体效率也要低很多，更需要进行深入研究。
发明内容
1.本发明的目的是提供一种有机电致发光材料和应用。该材料能发射红光，可作为发光材料应用在光电材料领域。本发明所制备的材料具有很好的热稳定性和光电性质，所采用的制备方法操作简单、反应条件温和。
本发明提供一种有机电致发光材料，其结构式为：
2.本发明提供的有机电致发光材料发光材料包括以下合成步骤：
1)将3,3',4,4'-联苯四胺和3,5-二叔丁基水杨醛通过缩合作用制备希夫碱配体H4L1
2)将希夫碱配体H4L1和K2PtCl4反应合成希夫碱铂配合物Pt2L1
3.本发明提供的有机电致发光材料，具有如下光物理性质：
1)分子式为：C72H90N4O4Pt2，分子量为：1465.70，Pt2L1为3,3',4,4'-联苯四胺缩3,5-二叔丁基水杨醛铂配合物。
2)在二甲基亚砜中的最大紫外吸收和荧光发射波长分别为564nm和648nm。
3)以饱和Ag/Ag+电极为参比电极，测试了材料的氧化还原(CV)曲线，所得起始氧化电位为+1.00V,通过经验公式[HOMO＝-(Eox+4.71)]eV计算得到材料的最高占有轨道(HOMO)的能级为-5.71eV，通过公式[LUMO＝HOMO+Eg]计算得到最低空轨道(LUMO)的能级为-3.65eV，其中能带隙[Eg＝1240/λmax]，Ag/Ag+电极电势为4.71V。
4)热分解温度为390℃。
5)将Pt2L1作为发光材料制备成有机电致发光二极管，取得了最大电流效率，流明效率，和亮度分别为：1.39cd·A-1,0.74lm·W-1and 1774cd·m-2。
6)本发明得到的有机电致发光材料是一种红光发光材料，该材料具有好的热稳定性，电化学性质和电致发光性质。该材料所采用的制备方法反应操作简单，条件温和，能够作为光电材料应用在电致发光领域。
附图说明
图1为本发明Pt2L1的磷光发射图。
图2为本发明Pt2L1的紫外可见吸收图。
图3为本发明Pt2L1的热重分析图。
图4为本发明Pt2L1的磷光寿命衰减图。
图5为本发明Pt2L1的循环伏安图。
图6为本发明Pt2L1的有机电致发光器件结构图。
图7为本发明Pt2L1的有机电致发光器件性质测试图。(a)电致发光谱图；(b)电流-电压和亮度-电压曲线；(c)外量子效率-电流曲线；(d)电流效率-电流和电压效率-电流曲线。
图8有机电致发光二极管器件测试性能参数。
具体实施方式
实施列1
1)取3,3'-二氨基联苯胺(100mg,0.47mmol)和3,5-二叔丁基水杨醛(475mg,1.90mmol)，置于50ml圆底烧瓶中，加入15ml的无水乙醇，磁力搅拌，回流6小时左右，在冷藏室中冷却至有大量红色固体析出，减压抽滤。用95％乙醇洗涤2～3次，放在干燥箱中烘干。产品为红色粉末，称重386mg，产率为76.4％。1HNMR(400MHz,CDCl3):δ13.67-13.65(m,4H,OH),8.74(m,4H,CH＝N),7.61(d,J＝8.7Hz,1H,Ar-H),7.54(d,J＝8.9Hz,1H,Ar-H),7.45(s,6H,Ar-H),7.40-7.31(m,4H,Ar-H),7.16(m,1H,Ar-H),7.09(s,1H,Ar-H),1.49-1.33(m,72H,CH3).IR(cm-1,KBr):3387,2957,2907,2870,2359,2342,1616,1589,1483,1439,1362,1252,1200,1171,980,878,822,773,644.HRMS(MALDI-TOF,positive mode,DHB):m/z＝1079.7909[M]+(C72H49N4O4Pt2:calcd.1079.5680).
2)取已经干燥好的席夫碱配体(200mg,0.185mmol)置于50ml圆底烧瓶，加入5mlDMF溶解，再加入干燥的氢氧化钾(42mg,0.75mmol)。同时称取K2PtCl4(166mg,0.40mmol)，并用3ml DMSO加热、溶解再加入反应烧瓶中。在无氧无水环境下反应24小时后，停止反应。用柱层析分离杂质和产物，得到红色固体产物50mg，产率18.5％。1HNMR(400MHz,CDCl3):δ9.03(dd,J＝37.6,13.0Hz,4H,CH＝N),8.26(d,J＝13.9Hz,1H,Ar-H),8.16(q,J＝14.8Hz,1H,Ar-H),7.75(d,J＝12.7Hz,2H,Ar-H),7.67(m,2H,Ar-H),7.43-7.29(m,8H,Ar-H),1.63-1.29(m,72H,CH3).IR(cm-1,KBr):3445,2950,2905,2866,2359,2322,1614,1580,1520,1481,1416,1387,1360,1258,1169,1130,928,891,635.HRMS(MALDI-TOF,positive mode,DHB):m/z＝1466.4808[M+H]+(C72H90N4O4Pt2:calcd.1465.7040).
实施列2
准确称取10mg希夫碱铂配合物溶解在二甲基亚砜中，制得1.0×10-5M溶液，准确移取3.0ml上述溶液加入比色皿中，然后在FLS980荧光仪上测定，激发狭缝和发射狭缝宽度都为10nm,激发波长为564nm。紫外吸收光谱的测定在Shimadzu UV-2450UV/Vis紫外可见吸仪器上测定。测试在室温和外界大气压下进行。发射和吸收测试图谱归一化结果见图1和图2。从图可知，最大紫外吸收波长为564nm,最大磷光发射波长为648nm.
实施列3
在氮气保护下，采用TA Instruments SDTQ600仪器进行该材料的热重分析(TGA)得到分解温度为390℃，升温速率都为10℃/分钟。测量结果如图3。
实施列4
准确称取10mg希夫碱铂配合物溶解在二甲基亚砜中，制得1.0×10-4M溶液。准确取4.0ml溶液加入10.0ml烧杯中，在AUTOLAB三电极系统中测试该化合物的循环伏安曲线，参比电极为饱和甘汞电极，支持电解质为0.1mol/l的四丁基六氟磷酸铵，室温下扫描速度为50mv/s.测量结果如图5.
实施列5
取ITO透明玻璃为阳极，超声清洗后干燥至于真空腔中，抽真空至5×10-5Pa，在上述阳极基板上真空蒸镀材料为MoO3，厚度为8nm的空穴注入层。在穴注入层上真空蒸镀NPB作为空穴传输层，蒸镀厚度为80nm。在空穴传输层上真空蒸镀mCP作为电子阻挡层，蒸镀厚度为10nm。在电子阻挡层上真空蒸镀mCP/PtL作为发光层，掺杂浓度为3wt％，蒸镀厚度为25nm。在发光层上真空蒸镀TPBI作为电子传输层，蒸镀厚度为40nm。在电子传输层上蒸镀材料为LiF，厚度为1nm的电子注入层。在电子注入层上蒸镀金属Al的阴极导电层，封装，得到电致发光器件。图6为本发明Pt2L1的有机电致发光器件结构图。
本应用实施例的电致发光器件电致发光谱图、电流-电压和亮度-电压曲线、外量子效率-电流曲线、电流效率-电流和电压效率-电流曲线如图7所示。从图中可以看出，以Pt2L1为发光材料制备的电致发光器件的电流效率最大值为1.39cd·A-1，流明效率最大值为0.74lm·W-1，亮度最大值为1774cd·m-2。图8为有机电致发光二极管器件测试性能参数。
实施列6
取ITO透明玻璃为阳极，超声清洗后干燥至于真空腔中，抽真空至5×10-5Pa，在上述阳极基板上真空蒸镀材料为MoO3，厚度为8nm的空穴注入层。在穴注入层上真空蒸镀NPB作为空穴传输层，蒸镀厚度为60nm。在空穴传输层上真空蒸镀mCP作为电子阻挡层，蒸镀厚度为10nm。在电子阻挡层上真空蒸镀mCP/PtL作为发光层，掺杂浓度为3wt％，蒸镀厚度为25nm。在发光层上真空蒸镀TPBI作为电子传输层，蒸镀厚度为40nm。在电子传输层上蒸镀材料为LiF，厚度为1nm的电子注入层。在电子注入层上蒸镀金属Al的阴极导电层，封装，得到电致发光器件。图6为本发明Pt2L1的有机电致发光器件结构图。
本应用实施例的电致发光器件电致发光谱图、电流-电压和亮度-电压曲线、外量子效率-电流曲线、电流效率-电流和电压效率-电流曲线如图7所示。从图中可以看出，以Pt2L1为发光材料制备的电致发光器件的电流效率最大值为1.33cd·A-1，流明效率最大值为0.76lm·W-1，亮度最大值为1521cd·m-2。图8为有机电致发光二极管器件测试性能参数。
本发明中所描述的具体实施例仅是对本发明精神作举例说明。本发明所属技术领域的技术人员可以对所描述的具体实施例做各种各样的修改或补充或采用类似的方式替代，但并不会偏离本发明的精神或者超越所附权利要求书所定义的范围。
Claims (6)
1.一种有机电致发光材料，其特征在于结构式为：
2.如权利要求1所述的有机电致发光材料的制备方法，其特征在于，包括如下步骤：
1)将3，3′，4，4′-联苯四胺和3，5-二叔丁基水杨醛通过缩合作用制备希夫碱配体H4L1；
2)将希夫碱配体H4L1和K2PtCl4反应合成希夫碱铂配合物Pt2L1。
3.根据权利要求2所述的一种有机电致发光材料的制备方法，其特征在于：步骤1)中所述的配体为希夫碱配体，使用3，3′，4，4′-联苯四胺和3，5-二叔丁基水杨醛以摩尔比1∶4制备。
4.根据权利要求2所述一种有机电致发光材料的制备方法，其特征在于：步骤2)中所述的配合物为希夫碱铂配合物，使用希夫碱配体和K2PtCl4以摩尔比1∶2制备。
5.如权利要求1所述的有机电致发光材料，其特征在于：所述的发光材料可应用在有机光电显示器中。
6.一种有机发光器件，包括第一电极、第二电极和置于所述两电极之间的一个或多个有机化合物层，其特征在于，至少一个有机化合物层包含如权利要求1所述的有机电致发光材料。
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