CN107987019A - 一种若丹明双吡唑乙酸酯有机激光材料的制备方法 - Google Patents
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Abstract
本发明提供了一种若丹明双吡唑乙酸酯有机激光材料的制备方法。本发明提供的若丹明双吡唑乙酸酯有机激光材料制备成本低，合成简单可控，产率高，溶解性好，同时具有较好的热稳定性。该材料在有机激光器件应用中表现出优异的热稳定性能、成膜稳定性和低阈值特性，低的水氧敏感性和高发光强度。其高的发光效率和迁移率，使其在电泵浦有机半导体激光、有机电致发光和有机场效应晶体管方面具有潜在的应用价值。
Description
技术领域
本发明属于激光材料领域，特别涉及一种若丹明双吡唑乙酸酯有机激光材料。
背景技术
传统的激光器存在着许多问题，如对于固体激光器，面临着晶体生长困难，技术要求高，价格昂贵等问题；激光玻璃一般需在高温条件下熔制，对于不同的基质材料和不同的激光工作波段还需要除去OH基和气体保护，工艺条件苛刻，生产成本高。目前使用较多的二氧化碳气体激光，虽然功率高，但其装置笨重庞大，给需要小型化激光器的场合带来了诸多不便。近年来，无机半导体激光得到了飞速的发展和广泛的应用，但是也存在生产成本高的问题。鉴于这些激光器性能上的局限性，科学家们长期以来一直致力于发展新型激光材料以期获得更加完美的激光器。探索和开发新型激光工作物质和材料不仅是未来研制新型高效率激光器及激光系统的前提和基础,而且具有巨大的潜在应用价值。
有机半导体材料由于其良好的光学及电学性能、简单的制备过程以及结构和性能的可调制性，在有机发光二极管(OLEDs)，有机场效应晶体管(OFETs)，有机太阳能电池(OPVs)及有机激光(OrganicLasers)等领域得到了广泛的应用，已经成为有机电子学研究的重要内容。近年来，结构紧凑、价格低廉(甚至可以弃置)的有机激光的研究发展非常迅速。与染料激光器相比，有机半导体材料除了具有有机激光染料的优点(高的发光效率，可调光谱范围宽，可视为四能级系统等)外，还具有高的固态发光效率，载流子传输及成膜性好等使其在激光应用方面受到广泛的关注。然而，由于有机激光在电泵浦下高的激光阈值导致电泵浦有机激光一直难以实现，这也成为一直困扰有机激光发展的瓶颈问题。为降低激光阈值，人们通过优化分子结构设计合成出包括小分子材料、聚合物材料及高分子材料等在内的有机半导体材料。其中具有多维空间拓扑结构单分散大分子，不但可以像小分子那样使用常规的硅胶柱层析进行提纯，还具有类似聚合物的良好的成膜性能。此外，由于它们所具有的空间多维结构减弱了分子间的相互作用，使得它们在极性溶剂中往往具有更好的溶解性形成表面形貌规整、均一的薄膜，同时该类材料还具有各向同性的光电性能。
发明内容
技术问题：为了解决现有技术的缺陷，本发明提供了一种稀土元素络合有机半导体激光材料。
技术方案：本发明提供的一种若丹明双吡唑乙酸酯有机激光材料，其化学式为：
该双吡唑乙酸香豆素衍生物激光材料的熔点在170.2以上。
该双吡唑乙酸香豆素衍生物激光材料在534-536nm之间。
该双吡唑乙酸香豆素衍生物激光材料的PL发射峰的半峰全宽在4.1nm以下。
该双吡唑乙酸香豆素衍生物激光材料的增益系数在92-97cm-1之间。
本发明还提供了上述若丹明双吡唑乙酸酯有机激光材料的制备方法，包括以下步骤：在三乙胺存在下，若丹明110和双(1-吡唑)乙酸反应，得双吡唑乙酸香豆素衍生物；反应式为：
其中，双(1-吡唑)、若丹明110、三乙胺的摩尔比为(1-1.2)：1：(2-4)，反应温度为室温，反应时间为3-5h。
本发明还提供了上述若丹明双吡唑乙酸酯有机激光材料在激光器中的应用。
有益效果：本发明提供的若丹明双吡唑乙酸酯有机激光材料制备成本低，合成简单可控，产率高，溶解性好，同时具有较好的热稳定性。该材料在有机激光器件应用中表现出优异的热稳定性能、成膜稳定性和低阈值特性，低的水氧敏感性和高发光强度。其高的发光效率和迁移率，使其在电泵浦有机半导体激光、有机电致发光和有机场效应晶体管方面具有潜在的应用价值。
具体实施方式
下面对本发明作出进一步说明。
实施例1
若丹明双吡唑乙酸酯有机激光材料的制备方法，包括以下步骤：在三乙胺存在下，若丹明110和双(1-吡唑)乙酸室温反应3-5h，得双吡唑乙酸香豆素衍生物；其中，双(1-吡唑)、若丹明110、三乙胺的摩尔比为1.1：1：3；收率85.6％；
反应式为：
实施例2
若丹明双吡唑乙酸酯有机激光材料的制备方法，包括以下步骤：在三乙胺存在下，若丹明110和双(1-吡唑)乙酸室温反应5h，得双吡唑乙酸香豆素衍生物；其中，双(1-吡唑)、若丹明110、三乙胺的摩尔比为1：1：2；收率84.2％。
实施例3
若丹明双吡唑乙酸酯有机激光材料的制备方法，包括以下步骤：在三乙胺存在下，若丹明110和双(1-吡唑)乙酸室温反应3h，得双吡唑乙酸香豆素衍生物；其中，双(1-吡唑)、若丹明110、三乙胺的摩尔比为1.2：1：4；收率83.6％。
实施例4
测试实施例1至3的若丹明双吡唑乙酸酯有机激光材料的溶解性，结果见表1。
表1
| 实施例1 | 实施例2 | 实施例3 | |
| 熔点℃ | 171.1-172.2 | 170.2-171.1 | 171.5-172.6 |
测试实施例1至3的若丹明双吡唑乙酸酯有机激光材料的溶解性，结果见表2。
表2
| 溶剂 | 实施例1 | 实施例2 | 实施例3 |
| 甲醇 | △ | △ | △ |
| 乙醇 | △ | △ | △ |
| 丙酮 | √ | √ | √ |
| 二氯甲烷 | √ | √ | √ |
| 四氢呋喃 | √ | √ | √ |
| DMF | √ | √ | √ |
| DMSO | √ | √ | √ |
| 甲苯 | △ | △ | △ |
| 环己烷 | × | × | × |
√：完全溶解；△：部分溶解；×，不溶解。
采用THF做溶剂，发光主体采用实施例1至3的若丹明双吡唑乙酸酯有机激光材料，分别配成20mg/mL的溶液。石英片经超声波清洗，采用旋涂的方式制备有机激光器件，旋涂条件为2000rpm，膜厚100nm左右。测定其性能，结果见表3。
表3
Claims (6)
1.一种若丹明双吡唑乙酸酯有机激光材料的制备方法，其特征在于：包括以下步骤：在三乙胺存在下，若丹明110和双(1-吡唑)乙酸反应，得双吡唑乙酸香豆素衍生物；反应式为：
2.根据权利要求3所述的一种若丹明双吡唑乙酸酯有机激光材料的制备方法，其特征在于：双(1-吡唑)、若丹明110、三乙胺的摩尔比为(1-1.2)：1：(2-4)，反应温度为室温，反应时间为3-5h。
3.根据权利要求3所述的一种若丹明双吡唑乙酸酯有机激光材料的制备方法，其特征在于：该双吡唑乙酸香豆素衍生物激光材料的熔点在170.2以上。
4.根据权利要求3所述的一种若丹明双吡唑乙酸酯有机激光材料的制备方法，其特征在于：该双吡唑乙酸香豆素衍生物激光材料在534-536nm之间。
5.根据权利要求3所述的一种若丹明双吡唑乙酸酯有机激光材料的制备方法，其特征在于：该双吡唑乙酸香豆素衍生物激光材料的PL发射峰的半峰全宽在4.1nm以下。
6.根据权利要求3所述的一种若丹明双吡唑乙酸酯有机激光材料的制备方法，其特征在于：该双吡唑乙酸香豆素衍生物激光材料的增益系数在92-97cm-1之间。
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| DE19843873A1 (de) * | 1998-09-25 | 2000-03-30 | Univ Halle Wittenberg | Verfahren zur Bestimmung von Proteaseaktivitäten auf Zelloberflächen |
| US20100233744A1 (en) * | 2009-03-11 | 2010-09-16 | Marker Gene Technologies, Inc. | Enzyme substrates for visualizing acidic organelles |
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| CN108129388A (zh) * | 2018-01-08 | 2018-06-08 | 深圳市佶达德科技有限公司 | 一种若丹明双吡唑乙酸酯有机激光材料及其应用 |
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