CN110128453B - 基于三苯胺和稀土配合物的白色有机电致发光材料制备方法及应用 - Google Patents
基于三苯胺和稀土配合物的白色有机电致发光材料制备方法及应用 Download PDFInfo
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Abstract
本发明涉及基于三苯胺和稀土配合物的白色有机电致发光材料制备方法及应用。合成的新白光材料以稀土铕配合物作为红光发色团,并组合了蓝光发射的三苯胺荧光团于一个分子内。利用不同发色团的红蓝两种光合理匹配,开发了一类能够发射高纯度白光的稀土有机小分子白光材料。该方法简单易行,得到的白光材料可用作液晶的背光源和固态照明,应用前景广泛。
Description
技术领域
本发明属于稀土配合物、有机化学和材料化学技术领域,涉及到稀土配合物和多功能有机发色团组合的白光材料合成。
背景技术
中国是世界上稀土资源最丰富的国家,素有“稀土王国”之称。但长期以来,由于稀土高科技附加值产品的缺乏,导致稀土被迫低价出口。开发基于稀土的高端下游产品,发挥稀土在荧光、磁性、激光、光纤通信、贮氢能源、超导等材料领域不可替代的作用,已成为当前科技工作者工作的重中之重,关系着国家的经济兴衰。
有机发光二极管(简称OLED)因为其自发光、驱动电压低、柔性显示、响应速度快等特性一直备受科学界和工业界人士关注。1994年,日本Kido课题组首次制备了发白光的白色有机发光二极管(WOLED),为OLED在固态照明领域的研究和应用开辟了先河(AppliedPhysics Letters,1994,64(7):815-7)。WOLED照明器件由于其在绿色环保和节约能源方面的绝对性优势而在全彩平板显示技术、液晶显示技术背光源,尤其是其在作为下一代固态照明光源方面显示出了巨大的应用潜力,成为科学界研究的热点领域。在制备成白色电致发光器件(WOLED)时,单分子白光材料相比于大多数共掺混色发光和多发光层的方法得到白光具有更好的可重复性,稳定性以及更简单的制备工序,可有效避免材料老化速度不同导致的器件不稳定性能以及多材料掺杂体系的材料之间能量转移问题。若实现此类单分子白光材料,则需要红、绿、蓝三原色或其中两种互补色发光材料的组装。
稀土荧光材料以其优异的荧光性能在发光材料领域受到广泛关注,其中稀土铕配合物的红光发射波长窄、荧光寿命长,性质介于无机和有机之间,具备好的发光性质并可作为载流子传输材料。本发明的发明人的在先申请CN104946239A公开了基于稀土铕和香豆素的单分子白光材料,但该材料激发波长和浓度对CIE的影响值较大,应用受限。
发明内容
本发明的目的之一是通过合理巧妙的设计将具有良好光物理性质的三苯胺蓝光发射团与香豆素有机荧光团用碳氮双键连接再与红光发射的稀土铕配合物集中于一个单分子白光材料,通过合理调控其激发波长和浓度,使红光和蓝光合理匹配得到较为纯正的白光发射。
本发明解决上述技术问题所采用的技术方案是:在合成易得的香豆素水合肼原料基础上,利用希夫碱反应引入稀土铕配位点,通过希夫碱上的氮原子,羰基上的氧原子,以及稀土铕配合物TTA(TTA-2-噻吩甲酰三氟丙酮)提供的氧原子配位点,和稀土铕形成螯合配合物,通过三苯胺和香豆素衍生物部分的蓝光发射和稀土铕配合物红光发射实现单分子的白光发射。其具体结构式如下:
本发明的目的之二是提供如下的方法来实现:
该材料的合成方法按如下步骤进行:
a、将香豆素水合肼和等摩尔的4-(二苯胺)苯甲醛化合物溶解于乙醇溶液中,加热至80℃回流二小时,反应液静止冷却,析出的固体过滤收集得黄色粉末CRTRP。
b、将a步骤得到的黄色固体粉末溶于乙醇溶液中,向溶液中滴加0.5倍摩尔的Eu(TTA)3(H2O)2的乙醇溶液,反应液于80℃加热回流六小时。反应液冷却至室温,正己烷扩散产生沉淀。沉淀过滤,粗产品用四氢呋喃重结晶。得到黄色目标产物WOLED-TRPEu。
本发明同时请求上述材料在白光有机发光材料上的应用,特别是用作液晶的背光源和固态照明。
相比于现有技术,本发明的有益效果是:
本发明巧妙地将具有良好光物理性质的三苯胺蓝光发射团与香豆素有机荧光团用碳氮双键连接,三苯胺由于其优异的光化学光物理性质,在有机电致发光材料中可作为蓝色发光材料。将稀土铕配合物的红光与三苯胺的蓝光发射组合于一个单分子材料内,通过组分间的合作和协同作用实现白光材料的开发。该单分子白光材料WOLED-TRPEu的紫外吸收光谱显示其主要吸收峰来自组成它的稀土铕配合物和香豆素三苯胺荧光团。其激发波长从380nm增加到405nm的过程中,其荧光颜色是红光发射,但激发波长从405nm再增大到435nm的过程中几乎只有白光发射。并且在白光材料WOLED-TRPEu浓度从10-6到5×10-5mol/L这个浓度范围时,当激发波长大于405nm后全部呈现为白光发射(相比于在先申请CN104946239A,其405nm后波长对白光材料WOLED-TRPEu的CIE值影响较小)。说明当激发波长大于405nm后,白光材料WOLED-TRPEu的红光和蓝光强度相当,即使浓度改变也能一直保持白光发射。当化合物WOLED-TRPEu浓度为30uM,激发波长为410nm时,此时其CIE坐标值为(0.34,0.32),接近于纯白光(0.33,0.33)。这个实验结果证明,化合物WOLED-TRPEu能够发射较纯正的白光,可以作为一种潜在的白色有机发光材料,为其走向工业化,作为大屏幕全色显示器、照明光源等高科技产品真正步入老百姓的生活提供广阔的前景。
附图说明
图1实施例1b的质谱谱图,其中图中还记载对应1125.1398,1203.1794和1655.4170的实验值和模拟值。
图2实施例1b紫外吸收光谱图。
图3实施例1b的不同激发波长下荧光光谱图,其中左图:WOLED-TRPEu(30μM,乙腈)当激发波长从380nm增加到405nm时的荧光光谱图;右图:激发波长从410nm到450nm处荧光光谱变化放大图。
图4实施例1b的不同激发波长下发光颜色变化图。
图5实施例1b荧光光谱CIE坐标值随激发波长和浓度变化图。
具体实施方式
为了更清楚地说明本发明内容,用具体实施例说明如下,具体实施例不限定本发明内容范围。
实施例1(白光材料WOLED-TRPEu的合成)
a.CRTRP的合成
香豆素水合肼(0.73mmol)和4-(二苯胺)苯甲醛(1.09mmol)溶解于乙醇溶液中,反应液于80℃加热回流二小时,TLC确定反应终点。反应液静置冷却,过滤,得固体产物327mg.收率:85%.1H-NMR(400MHz,CDCl3):δ(ppm)11.79(s,1H,-CO-NH-),8.84(s,1H,–N=CH-),8.12(s,1H,ArH),7.65(d,2H,J=8.8Hz,ArH),7.47(d,1H,J=8.8Hz,ArH),7.29(t,2H,J=8.0Hz,ArH),7.13(d,2H,J=8.0Hz,ArH),7.02-7.08(m,4H,ArH),6.68(d,2H,J=8.8Hz,ArH),6.53(s,1H,ArH),3.47(q,4H,J=7.2Hz,-CH2CH3),1.25(t,6H,J=7.2Hz,-CH2CH3).13CNMR(100MHz,CDCl3):δ(ppm)162.8,159.6,157.7,152.8,149.9,149.0,148.5,147.1,131.4,129.4,128.9,127.0,125.3,123.8,121.8,110.3,109.3,108.7,96.7,45.2,12.4.TOF MS calcd for C33H30N4O3530.2318,found530.2316.
b.WOLED-TRPEu的合成
化合物CRTRP(0.20mmol)溶解于30毫升乙醇溶液中,慢慢滴入Eu(TTA)3(H2O)2的乙醇溶液(0.10mmol),反应液于80℃加热回流搅拌六小时。反应液静置冷却,过滤,得粗产品,乙醇重结晶。收率:80%.HRMS(ESI)calculated for[Eu(TTA)2(CRTRP)2]+1655.36,found1655.42.HRMS(ESI)calculated for[Eu(TTA)2(CRTRP)]+1125.1,found 1125.1.
实施例2(质谱测定)
WOLED-TRPEu在乙腈中的质谱如附图1所示,只有三个明显的峰1125.1398,1203.1794和1655.4170这几个峰分别对应[Eu(TTA)2(CRTRP)]+,[Eu(TTA)2(CRTRP)+CH3OH+C2H5OH]+和[Eu(TTA)2(CRTRP)2]+,这与IsoPro 3.0 program的模拟结果相符,实验数据和理论计算结果能够很好地吻合。说明化合物WOLED-TRPEu在溶液中是能够稳定存在的。
实施例3(实施例1b紫外吸收光谱测定)
称取实施例1中合成的CRTRP和WOLED-TRPEu以及Eu(TTA)3,分别配制成10-5μm的乙腈溶液,测定其紫外吸收光谱,测试结果见附图2。CRTRP的紫外最大吸收峰在432nm(logε=4.85)处,铕配合物的紫外最大吸收峰在336nm(logε=4.71)处。化合物WOLED-TRPEu的紫外吸收光谱上有两个明显的特征吸收峰,一个是336nm(logε=4.75)处的紫外吸收,这个峰和铕配合物峰是相吻合的,应当归属于Eu的配合物特征吸收。另一个就是438nm(logε=4.74)处的紫外吸收,这说明和铕配位后,属于CRTRP的432nm处特征吸收峰的红移至438nm处,这可能是由于和金属配位后分子极性增大的原因。
实施例4(实施例1b在不同激发波长下荧光光谱测定)
称取实施例1b中合成的化合物WOLED-TRPEu配制成10-5μm的乙腈溶液,测试其在不同激发波长时其荧光发射光谱的变化,测试结果见附图3所示。其组成中铕配合物和香豆素部分的最大吸收峰的不同使其在不同位置的激发波长激发时,两个部分的荧光强度也发生了明显的变化。如附图3所示,当激发波长从380nm处增加到405nm处,这一过程中,荧光光谱都是稀土铕配合物的红光发射占主导,肉眼看到的只有红色荧光发射。当激发波长继续增大,稀土铕的红色荧光逐渐减弱,而属于香豆素部分的蓝光发射逐渐增强,红光和蓝光是互补色,当激发波长在到一定值时,由于荧光强度匹配,化合物CRTRP-Eu就发射出明显的白光。如附图4所示,通过调节化合物CRTRP-Eu的激发波长可以调控其荧光发射的颜色的变化。其激发波长从380nm增加到430nm的过程中,其荧光颜色变化明显,从红色变到近乎白光发射。
实施例5(实施例1b不同激发波长下发光颜色变化图)
称取实施例1中的材料WOLED-TRPEu配制成10-5μm的乙腈溶液,当激发波长从380nm变化到430nm时观察其发光颜色的变化,测试结果见附图4。
实施例6(实施例1b荧光光谱CIE坐标值随激发波长和浓度的变化)
称取实施例1中b步骤的材料配制成不同浓度的乙腈溶液,分别测试其在不同激发波长下的CIE坐标值,测试结果见附图5。当化合物WOLED-TRPEu浓度1uM时,380nm处激发波长只能看到红色荧光,此时其荧光颜色为红色,处于CIE坐标图中的红色区域,当激发波长逐渐增加,其蓝色荧光逐渐增强,其CIE坐标逐渐改变成白光。并且,随着化合物WOLED-TRPEu浓度的增大,由于香豆素部分的缔合,蓝光向绿光过渡,化合物WOLED-TRPEu的CIE的坐标也逐渐靠向绿光区。当化合物WOLED-TRPEu浓度为30uM,激发波长为410nm时,此时其CIE坐标值为(0.34,0.32),接近于纯白光(0.33,0.33)。这个实验结果证明,合理调控化合物的激发波长的浓度,化合物WOLED-TRPEu能够发射较纯正的白光,这为进一步开发单分子白色有机发光材料提供了基础。
Claims (4)
2.根据权利要求1所述的基于三苯胺和稀土配合物的白色有机电致发光材料的制备方法,其特征在于,包括以下步骤:
a、将香豆素水合肼和等摩尔的4-(二苯胺)苯甲醛化合物溶解于乙醇溶液中,加热至80℃回流二小时,反应液静止冷却,析出的固体过滤收集得黄色粉末CRTRP;
b、将a步骤得到的黄色固体粉末溶于乙醇溶液中,向溶液中滴加0.5倍摩尔的Eu(TTA)3(H2O)2的乙醇溶液,反应液于80℃加热回流六小时,反应液冷却至室温,正己烷扩散产生沉淀,沉淀过滤,粗产品用四氢呋喃重结晶,得到黄色目标产物WOLED-TRPEu。
3.权利要求1所述的材料在白色有机发光材料上的应用。
4.根据权利要求3所述的应用,其特征在于,用作液晶的背光源和固态照明。
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