CN112300052A - 一种化合物及其应用、包含其的有机电致发光器件 - Google Patents
一种化合物及其应用、包含其的有机电致发光器件 Download PDFInfo
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- CN112300052A CN112300052A CN201910663658.3A CN201910663658A CN112300052A CN 112300052 A CN112300052 A CN 112300052A CN 201910663658 A CN201910663658 A CN 201910663658A CN 112300052 A CN112300052 A CN 112300052A
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- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000005579 tetracene group Chemical group 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
技术领域
本发明涉及有机电致发光技术领域,特别涉及一种新型化合物及其应用、以及包含该化合物的有机电致发光器件。
背景技术
近年来,基于有机材料的光电子器件已经变得越来越受欢迎。有机材料固有的柔性令其十分适合用于在柔性基板上制造,可根据需求设计、生产出美观而炫酷的光电子产品,获得相对于无机材料无以比拟的优势。此类有机光电子器件的示例包括有机发光二极管(OLED),有机场效应管,有机光伏打电池,有机传感器等。其中OLED发展尤其迅速,已经在信息显示领域取得商业上的成功。OLED可以提供高饱和度的红、绿、蓝三颜色,用其制成的全色显示装置无需额外的背光源,具有色彩炫丽,轻薄柔软等优点。
OLED器件核心为含有多种有机功能材料的薄膜结构。常见的功能化有机材料有:空穴注入材料、空穴传输材料、空穴阻挡材料、电子注入材料、电子传输材料,电子阻挡材料以及发光主体材料和发光客体(染料)等。通电时,电子和空穴被分别注入、传输到发光区域并在此复合,从而产生激子并发光。
人们已经开发出多种有机材料,可以提升载流子迁移率、调控载流子平衡、突破电致发光效率、延缓器件衰减。出于量子力学的原因,常见的荧光发光体主要利用电子和空血结合时产生的单线态激子发光,现在仍然广泛地应用于各种OLED产品中。有些金属络合物如铱络合物,可以同时利用三线态激子和单线态激子进行发光,被称为磷光发光体,其能量转换效率可以比传统的荧光发光体提升高达四倍。热激发延迟荧光(TADF)技术通过促进三线态激子朝单线态激子的转变,在不采用金属配合物的情况下,仍然可以有效地利用三线态激子而实现较高的发光效率。热激发敏化荧光(TASF)技术则采用具TADF性质的材料,通过能量转移的方式来敏化发光体,同样可以实现较高的发光效率。
随着OLED产品逐步进入市场,人们对这类产品的性能有越来越高的要求。当前使用的OLED材料和器件结构无法完全解决OLED产品效率、寿命、成本等各方面的问题。本发明的研究人员通过认真思考和不断实验,发现了一种巧妙的分子设计方案,并在下文中详细地进行说明。令人惊讶地,本发明所揭示的化合物非常适合应用于OLED并提升器件的性能。
发明内容
本发明的目的是设计一种具有稠环并咔唑结构的化合物,通过对取代基以及取代位置的选择,确保该类化合物具有较大的共轭平面具有较强的传输能力和较好的薄膜形态,进而获得热稳定性和光学稳定性较好、传输性能好的新型发光层主体材料。
本发明提供了一种由如下通式(1)表示的化合物,
其中:L1选自单键、取代或未取代的C6-C30的亚芳基、取代或未取代的C3~C30亚杂芳基中的一种;
Ar1选自取代或未取代的C6~C30芳基、取代或未取代的C3~C30的杂芳基中的一种;
X1~X14分别独立的为CR1,所述R1独立地选自氢、C1~C12烷基、C3~C12环烷基、C1~C12烷氧基、卤素、氰基、硝基、羟基、硅烷基、氨基、取代或未取代的C6~C30芳基氨基、取代或未取代的C3~C30杂芳基氨基、取代或未取代的C6~C30芳基、取代或未取代的C3~C30杂芳基中的一种;
进一步优选的,式(1)中,L1为单键。
进一步优选的,式(1)中,所述Ar1选自取代或未取代的C6~C30芳基、取代或未取代的C2~C30的吸电子杂芳基中的一种。
再进一步优选的,所述Ar1选自取代或未取代的下述基团:苯基、萘基、联苯基、三联苯基、三亚苯基、芴基、咔唑基、菲基、二苯并呋喃基、二苯并噻吩基、吡啶基、嘧啶基、三嗪基、喹啉基、喹唑啉基、喹喔啉基、菲咯啉基中的一种或多种的组合;
进一步优选的,式(1)中,所述X7和X8分别为的CR1中,R1独立地选自取代或未取代的C6~C30芳基、取代或未取代的C3~C30供电子杂芳基中的一种;
再进一步优选的,式(1)中,所述X7和X8分别选自的CR1中,R1选自取代或未取代的下述基团:芳胺基、苯基、萘基、联苯基、三联苯基、三亚苯基、芴基、咔唑基、菲基、二苯并呋喃基、二苯并噻吩基中的一种;
在本发明中,如所述取代或未取代的C6~C30芳基中的C6~C30表示基团中碳原子数目。除非特殊说明,一般而言该碳原子数不包括取代基的碳原子数。
本发明中,对于化学元素的表述包含化学性质相同的同位素的概念,例如“氢”的表述,也包括化学性质相同的“氘”、“氚”的概念。
作为上述取代或未取代的C6~C30芳基,优选具有6-20个骨架碳原子,优选所述芳基为由苯基、联苯基、三联苯基、萘基、蒽基、菲基、茚基、芴基及其衍生物、荧蒽基、三亚苯基、芘基、苝基、基和并四苯基所组成的组中的基团。所述联苯基选自2-联苯基、3-联苯基和4-联苯基;所述三联苯基包括对-三联苯基-4-基、对-三联苯基-3-基、对-三联苯基-2-基、间-三联苯基-4-基、间-三联苯基-3-基和间-三联苯基-2-基;所述萘基为1-萘基或2-萘基;所述蒽基选自由1-蒽基、2-蒽基和9-蒽基所组成的组中;所述芴基选自由1-芴基、2-芴基、3-芴基、4-芴基和9-芴基所组成的组中;所述芴基衍生物选自由9,9’-二甲基芴,9,9’-螺二芴和苯并芴所组成的组中;所述芘基选自由1-芘基、2-芘基和4-芘基所组成的组中;所述并四苯基选自由1-并四苯基、2-并四苯基和9-并四苯基所组成的组中。
作为取代或未取代的C6~C30杂芳基,优选具有6-20个骨架碳原子,优选所述杂芳基为呋喃基、噻吩基、吡咯基、苯并呋喃基、苯并噻吩基、异苯并呋喃基、吲哚基、二苯并呋喃基、二苯并噻吩基、咔唑基及其衍生物,其中,所述咔唑基衍生物优选为9-苯基咔唑、9-萘基咔唑苯并咔唑、二苯并咔唑、或吲哚并咔唑。
作为本发明涉及的化合物的优选结构,可以举出以下C1~C306所示结构的化合物,但不限于这些化合物:
具体实施方式
下面将以多个合成实施例为例来详述本发明的上述新化合物的具体制备方法,但本发明的制备方法并不限于这些合成实施例。
本发明中所用的各种化学药品如石油醚、乙酸乙酯、硫酸钠、甲苯、四氢呋喃、二氯甲烷、乙酸、磷酸钾、叔丁醇钠等基础化工原料均购自上海泰坦科技股份有限公司和西陇化工股份有限公司,其它中间体通过定制获得。确定下述化合物所用的质谱仪采用的是ZAB-HS型质谱仪测定(英国Micromass公司制造)。
下面对本发明化合物的合成方法进行简要的说明。
代表性合成路径:
通过替换不同的Br-L-Ar1可以获得不同的目标化合物。
合成实施例1
化合物C1的合成:
在500ml单口瓶中,加入15g(31.94mmol)中间体化合物C、6.2g(38.33mmol)溴苯、292.52mg(391.44umol)三(二亚苄基丙酮)二钯(即Pd2(dba)3)、262.28mg(638.88umol)2-双环己基膦-2',6'-二甲氧基联苯(即sphos),300ml甲苯(Toluene),4.6g(47.92mmol)叔丁醇钠(NaOBu-t),抽真空换氮气3次,反应升温至110℃反应5h。反应完毕,停止反应。冷却至室温,对反应液分液,浓缩有机相,进行硅胶柱层析得化合物C1.M/Z理论值:545,M/Z实测值:546。
合成实施例2
化合物C2的合成
在500ml单口瓶中,加入15g(31.94mmol)中间体C、10.47g(38.33mmol)2-溴-9,9-二甲基芴、292.52mg(391.44umol)三(二亚苄基丙酮)二钯(即Pd2(dba)3)、262.28mg(638.88umol)2-双环己基膦-2',6'-二甲氧基联苯(即sphos),300ml甲苯(Toluene),4.6g(47.92mmol)叔丁醇钠(NaOBu-t),抽真空换氮气3次,反应升温至110℃反应5h。反应完毕,停止反应。冷却至室温,对反应液分液,浓缩有机相,进行硅胶柱层析得化合物C2.M/Z理论值:661,M/Z实测值:662。
合成实施例3
化合物C3的合成
在500ml单口瓶中,加入15g(31.94mmol)中间体化合物C、8.94g(38.33mmol)4-溴联苯、292.52mg(391.44umol)三(二亚苄基丙酮)二钯(即Pd2(dba)3)、262.28mg(638.88umol)2-双环己基膦-2',6'-二甲氧基联苯(即sphos),300ml甲苯(Toluene),4.6g(47.92mmol)叔丁醇钠(NaOBu-t),抽真空换氮气3次,反应升温至110℃反应5h。反应完毕,停止反应。冷却至室温,对反应液分液,浓缩有机相,进行硅胶柱层析得化合物C3.M/Z理论值:621,M/Z实测值:622。
合成实施例4
化合物C21的合成
在500ml单口瓶中,加入15g(31.94mmol)中间体化合物C、12.39g(38.33mmol)2-(4-溴苯基)二苯并呋喃、292.52mg(391.44umol)三(二亚苄基丙酮)二钯(即Pd2(dba)3)、262.28mg(638.88umol)2-双环己基膦-2',6'-二甲氧基联苯(即sphos),300ml甲苯(Toluene),4.6g(47.92mmol)叔丁醇钠(NaOBu-t),抽真空换氮气3次,反应升温至110℃反应5h。反应完毕,停止反应。冷却至室温,对反应液分液,浓缩有机相,进行硅胶柱层析得化合物C21.M/Z理论值:711,M/Z实测值:712。
合成实施例5
化合物C38的合成
在500ml单口瓶中,加入15g(31.94mmol)中间体化合物C、12.39g(38.33mmol)2-溴萘、292.52mg(391.44umol)三(二亚苄基丙酮)二钯(即Pd2(dba)3)、262.28mg(638.88umol)2-双环己基膦-2',6'-二甲氧基联苯(即sphos),300ml甲苯(Toluene),4.6g(47.92mmol)叔丁醇钠(NaOBu-t),抽真空换氮气3次,反应升温至110℃反应5h。反应完毕,停止反应。冷却至室温,对反应液分液,浓缩有机相,进行硅胶柱层析得化合物C38.M/Z理论值:595,M/Z实测值:596。
合成实施例6
化合物C82的合成
在500ml单口瓶中,加入15g(28.87mmol)中间体化合物a、9.46g(34.64mmol)2-溴-9,9-二甲基芴、264.34mg(288.67umol)三(二亚苄基丙酮)二钯(即Pd2(dba)3)、237.01mg(577.33umol)2-双环己基膦-2',6'-二甲氧基联苯(即sphos),300ml甲苯(Toluene),4.16g(43.30mmol)叔丁醇钠(NaOBu-t),抽真空换氮气3次,反应升温至110℃反应5h。反应完毕,停止反应。冷却至室温,对反应液分液,浓缩有机相,进行硅胶柱层析得化合物C82。M/Z理论值:711,M/Z实测值:712。
合成实施例7
化合物C83的合成
在500ml单口瓶中,加入15g(28.87mmol)中间体化合物a、8.07g(34.64mmol)4-溴联苯、264.34mg(288.67umol)三(二亚苄基丙酮)二钯(即Pd2(dba)3)、237.01mg(577.33umol)2-双环己基膦-2',6'-二甲氧基联苯(即sphos),300ml甲苯(Toluene),4.16g(43.30mmol)叔丁醇钠(NaOBu-t),抽真空换氮气3次,反应升温至110℃反应5h。反应完毕,停止反应。冷却至室温,对反应液分液,浓缩有机相,进行硅胶柱层析得化合物C83.M/Z理论值:671,M/Z实测值:672。
合成实施例8
化合物C90的合成
在500ml单口瓶中,加入15g(28.87mmol)中间体化合物a、8.56g(34.64mmol)4-溴二苯并呋喃、264.34mg(288.67umol)三(二亚苄基丙酮)二钯(即Pd2(dba)3)、237.01mg(577.33umol)2-双环己基膦-2',6'-二甲氧基联苯(即sphos),300ml甲苯(Toluene),4.16g(43.30mmol)叔丁醇钠(NaOBu-t),抽真空换氮气3次,反应升温至110℃反应5h。反应完毕,停止反应。冷却至室温,对反应液分液,浓缩有机相,进行硅胶柱层析得化合物C90.M/Z理论值:685,M/Z实测值:686。
合成实施例9
化合物C121的合成
在500ml单口瓶中,加入16g(50mmol)中间体化合物B、8g(50mmol)溴苯、230.57mg(251.79umol)三(二亚苄基丙酮)二钯(即Pd2(dba)3)、206.74mg(503.58umol)2-双环己基膦-2',6'-二甲氧基联苯(即sphos),300ml甲苯(Toluene),15g(150mmol)叔丁醇钠(NaOBu-t),抽真空换氮气3次,反应升温至110℃反应5h。反应完毕,停止反应。冷却至室温,对反应液分液,浓缩有机相,进行硅胶柱层析得化合物C121.M/Z理论值:393,M/Z实测值:394。
合成实施例10
化合物C215的合成
在500ml单口瓶中,加入16g(50mmol)中间体化合物D、14g(50mmol)Z-1及1.7g60%的NaH,加完后在氮气氛围中升温至100℃反应5h。反应完毕,停止反应。冷却至室温,对反应液分液,浓缩有机相,进行硅胶柱层析得化合物C215.M/Z理论值:548,M/Z实测值:549。
合成实施例11
化合物C223的合成
在500ml单口瓶中,加入16g(50mmol)中间体化合物D、20.5g(50mmol)Z-2、230.57mg(251.79umol)三(二亚苄基丙酮)二钯(即Pd2(dba)3)、206.74mg(503.58umol)2-双环己基膦-2',6'-二甲氧基联苯(即sphos),300ml甲苯(Toluene),3.63g(37.77mmol)叔丁醇钠(NaOBu-t),抽真空换氮气3次,反应升温至110℃反应5h。反应完毕,停止反应。冷却至室温,对反应液分液,浓缩有机相,进行硅胶柱层析得化合物C223.M/Z理论值:648,M/Z实测值:649。
合成实施例12
化合物C245的合成
在500ml单口瓶中,加入28g(50mmol)中间体化合物E、14g(50mmol)Z-1及1.7g60%的NaH,加完后在氮气氛围中升温至100℃反应5h。反应完毕,停止反应。冷却至室温,对反应液分液,浓缩有机相,进行硅胶柱层析得化合物C245.M/Z理论值:789,M/Z实测值:790。
合成实施例13
化合物C271的合成
在500ml单口瓶中,加入28g(50mmol)中间体化合物E、19.5g(50mmol)Z-3、230.57mg(251.79umol)三(二亚苄基丙酮)二钯(即Pd2(dba)3)、206.74mg(503.58umol)2-双环己基膦-2',6'-二甲氧基联苯(即sphos),300ml甲苯(Toluene),3.63g(37.77mmol)叔丁醇钠(NaOBu-t),抽真空换氮气3次,反应升温至110℃反应5h。反应完毕,停止反应。冷却至室温,对反应液分液,浓缩有机相,进行硅胶柱层析得化合物C271.M/Z理论值:865,M/Z实测值:866。
合成实施例14
化合物C278的合成
在500ml单口瓶中,加入23.5g(50mmol)中间体化合物F、19.5g(50mmol)Z-3、230.57mg(251.79umol)三(二亚苄基丙酮)二钯(即Pd2(dba)3)、206.74mg(503.58umol)2-双环己基膦-2',6'-二甲氧基联苯(即sphos),300ml甲苯(Toluene),3.63g(37.77mmol)叔丁醇钠(NaOBu-t),抽真空换氮气3次,反应升温至110℃反应5h。反应完毕,停止反应。冷却至室温,对反应液分液,浓缩有机相,进行硅胶柱层析得化合物C278.M/Z理论值:776,M/Z实测值:777。
合成实施例15
化合物C283的合成
在500ml单口瓶中,加入15.5g(50mmol)中间体化合物D、12g(50mmol)Z-4及1.7g60%的NaH,加完后在氮气氛围中升温至100℃反应5h。反应完毕,停止反应。冷却至室温,对反应液分液,浓缩有机相,进行硅胶柱层析得化合物C283.M/Z理论值:521,M/Z实测值:522。
合成实施例16
化合物C301的合成
在500ml单口瓶中,加入16g(50mmol)中间体化合物D、20g(50mmol)Z-5、230.57mg(251.79umol)三(二亚苄基丙酮)二钯(即Pd2(dba)3)、206.74mg(503.58umol)2-双环己基膦-2',6'-二甲氧基联苯(即sphos),300ml甲苯(Toluene),3.63g(37.77mmol)叔丁醇钠(NaOBu-t),抽真空换氮气3次,反应升温至110℃反应5h。反应完毕,停止反应。冷却至室温,对反应液分液,浓缩有机相,进行硅胶柱层析得化合物C301.M/Z理论值:647,M/Z实测值:648。
合成实施例17
化合物C306的合成
在500ml单口瓶中,加入23.5g(50mmol)中间体化合物G、24.3g(50mmol)Z-6、230.57mg(251.79umol)三(二亚苄基丙酮)二钯(即Pd2(dba)3)、206.74mg(503.58umol)2-双环己基膦-2',6'-二甲氧基联苯(即sphos),300ml甲苯(Toluene),3.63g(37.77mmol)叔丁醇钠(NaOBu-t),抽真空换氮气3次,反应升温至110℃反应5h。反应完毕,停止反应。冷却至室温,对反应液分液,浓缩有机相,进行硅胶柱层析得化合物C306.M/Z理论值:875,M/Z实测值:876。
器件实施例
OLED包括位于第一电极和第二电极,以及位于电极之间的有机材料层。该有机材料又可以分为多个区域。比如,该有机材料层可以包括空穴传输区、发光层、电子传输区。
在具体实施例中,在第一电极下方或者第二电极上方可以使用基板。基板均为具有机械强度、热稳定性、防水性、透明度优异的玻璃或聚合物材料。此外,作为显示器用的基板上也可以带有薄膜晶体管(TFT)。
第一电极可以通过在基板上溅射或者沉积用作第一电极的材料的方式来形成。当第一电极作为阳极时,可以采用铟锡氧(ITO)、铟锌氧(IZO)、二氧化锡(SnO2)、氧化锌(ZnO)等氧化物透明导电材料和它们的任意组合。第一电极作为阴极时,可以采用镁(Mg)、银(Ag)、铝(Al)、铝-锂(Al-Li)、钙(Ca)、镁-铟(Mg-In)、镁-银(Mg-Ag)等金属或合金以及它们之间的任意组合。
有机材料层可以通过真空热蒸镀、旋转涂敷、打印等方法形成于电极之上。用作有机材料层的化合物可以为有机小分子、有机大分子和聚合物,以及它们的组合。
空穴传输区位于阳极和发光层之间。空穴传输区可以为单层结构的空穴传输层(HTL),包括只含有一种化合物的单层空穴传输层和含有多种化合物的单层空穴传输层。空穴传输区也可以为包括空穴注入层(HIL)、空穴传输层(HTL)、电子阻挡层(EBL)中的至少一层的多层结构。
空穴传输区中的空穴传输材料、电子阻挡材料选自、但不限于酞菁衍生物如CuPc、导电聚合物或含导电掺杂剂的聚合物如聚苯撑乙烯、聚苯胺/十二烷基苯磺酸(Pani/DBSA)、聚(3,4-乙撑二氧噻吩)/聚(4-苯乙烯磺酸盐)(PEDOT/PSS)、聚苯胺/樟脑磺酸(Pani/CSA)、聚苯胺/聚(4-苯乙烯磺酸盐)(Pani/PSS)、芳香胺衍生物如下面HT-1至HT-34所示的化合物;或者其任意组合。
空穴注入层位于阳极和空穴传输层之间。空穴注入层可以是单一化合物材料,也可以是多种化合物的组合。例如,空穴注入层可以采用上述HT-1至HT-34的一种或多种化合物,或者采用下述HI-1-HI-3中的一种或多种化合物;也可以采用HT-1至HT-34的一种或多种化合物掺杂下述HI-1-HI-3中的一种或多种化合物。
发光层包括可以发射不同波长光谱的发光染料(即掺杂剂,dopant),还可以同时包括主体材料(Host)。发光层可以是发射红、绿、蓝等单一颜色的单色发光层。多种不同颜色的单色发光层可以按照像素图形进行平面排列,也可以堆叠在一起而形成彩色发光层。当不同颜色的发光层堆叠在一起时,它们可以彼此隔开,也可以彼此相连。发光层也可以是能同时发射红、绿、蓝等不同颜色的单一彩色发光层。
根据不同的技术,发光层材料可以采用荧光电致发光材料、磷光电致发光材料、热活化延迟荧光发光材料等不同的材料。在一个OLED器件中,可以采用单一的发光技术,也可以采用多种不同的发光技术的组合。这些按技术分类的不同发光材料可以发射同种颜色的光,也可以发射不同种颜色的光。
在本发明的一方面,发光层采用磷光电致发光的技术。其发光层主体材料选自、但不限于本发明式(1)所示的一种或多种化合物的组合;或者选自、但不限于本发明式(1)所示的一种或多种化合物同GPH-1至GPH-80中的一种或多种的组合。
在本发明的一方面,发光层采用磷光电致发光的技术。其发光层磷光掺杂剂可以选自、但不限于以下所罗列的GPD-1至GPD-47的一种或多种的组合。
其中D为氘。
在本发明的一方面,发光层采用磷光电致发光的技术。其发光层磷光掺杂剂可以选自、但不限于以下所罗列的RPD-1至RPD-28的一种或多种的组合。
在本发明的一方面,发光层采用磷光电致发光的技术。其发光层磷光掺杂剂可以选自、但不限于以下所罗列的YPD-1—YPD-11的一种或多种的组合。
OLED有机材料层还可以包括发光层与阴极之间的电子传输区。电子传输区可以为单层结构的电子传输层(ETL),包括只含有一种化合物的单层电子传输层和含有多种化合物的单层电子传输层。电子传输区也可以为包括电子注入层(EIL)、电子传输层(ETL)、空穴阻挡层(HBL)中的至少一层的多层结构。
本发明的一方面,电子传输层材料可以选自、但不限于以下所罗列的ET-1至ET-57的一种或多种的组合。
器件中还可以包括位于电子传输层与阴极之间的电子注入层,电子注入层材料包括但不限于以下罗列的一种或多种的组合:LiQ,LiF,NaCl,CsF,Li2O,Cs2CO3,BaO,Na,Li,Ca。
相对于现有技术,本发明具有以下有益效果:
在本发明中化合物具有特定的内向扭曲的稠环并咔唑结构,该结构使该系列化合物均能获得很好的三线态能级;其次,该内向扭曲结构能够有效控制材料的结晶性能,这对后期制备的无定型态薄膜在器件中的稳定性极为有利,有效的提高了由其所制备的器件的稳定性能。
实施例1
本实施例中有机电致发光器件制备过程如下:
将涂布了ITO透明导电层的玻璃板在商用清洗剂中超声处理,在去离子水中冲洗,在丙酮:乙醇混合溶剂中超声除油,在洁净环境下烘烤至完全除去水份,用紫外光和臭氧清洗,并用低能阳离子束轰击表面;
把上述带有阳极的玻璃基片置于真空腔内,抽真空至<1×10-5,在上述阳极层膜上真空蒸镀HI-3作为空穴注入层,蒸镀速率为0.1nm/s,蒸镀膜厚为10nm;
在空穴注入层之上真空蒸镀HT-4作为器件的空穴传输层,蒸镀速率为0.1nm/s,蒸镀总膜厚为80nm;
在空穴传输层之上,真空蒸镀HT-14作为器件的电子阻挡层,蒸镀速率为0.1nm/s,蒸镀总膜厚为80nm;
在电子阻挡层之上真空蒸镀器件的发光层,发光层包括主体材料和染料材料,利用多源共蒸的方法,调节主体材料C1:GPH-59(比例为2:6)蒸镀速率为0.1nm/s,染料RPD-8蒸镀速率3%比例设定,蒸镀总膜厚为30nm,主体材料:染料RPD-8质量比为97:3;
在发光层之上真空蒸镀器件的电子传输层材料ET-46,50%的比例设定和ET-57,50%的比例设定,其蒸镀速率为0.1nm/s,蒸镀总膜厚为30nm;
在电子传输层(ETL)上真空蒸镀厚度为0.5nm的LiF作为电子注入层,厚度为150nm的Al层作为器件的阴极。
实施例2
本实施例中有机电致发光器件制备过程与实施例1中相同,区别仅在于将化合物C1替换为化合物C2。
实施例3
本实施例中有机电致发光器件制备过程与实施例1中相同,区别仅在于将化合物C1替换为化合物C3。
实施例4
本实施例中有机电致发光器件制备过程与实施例1中相同,区别仅在于将化合物C1替换为化合物C21。
实施例5
本实施例中有机电致发光器件制备过程与实施例1中相同,区别仅在于将化合物C1替换为化合物C38。
实施例6
本实施例中有机电致发光器件制备过程与实施例1中相同,区别仅在于将化合物C1替换为化合物C82。
实施例7
本实施例中有机电致发光器件制备过程与实施例1中相同,区别仅在于将化合物C1替换为化合物C83。
实施例8
本实施例中有机电致发光器件制备过程与实施例1中相同,区别仅在于将化合物C1替换为化合物C90。
实施例9
本实施例中有机电致发光器件制备过程与实施例1中相同,区别仅在于将化合物C1替换为化合物C164。
对比例1
在该对比例中,有机电致发光器件制备过程与实施例1中相同,区别仅在于,将化合物C1替换为现有技术中的化合物I(a)作为主体材料,所述的I(a)结构如下。
对实施例1-9和对比例1制备的有机电致发光器件进行如下性能测定:
在同样亮度下,使用数字源表及亮度计测定实施例1-9和对比例1制备得到的有机电致发光器件的驱动电压和电流效率以及器件的寿命。具体而言,以每秒0.1V的速率提升电压,测定当有机电致发光器件的亮度达到5000cd/m2时的电压即驱动电压,同时测出此时的电流密度;亮度与电流密度的比值即为电流效率;LT95的寿命测试如下:使用亮度计在5000cd/m2亮度下,保持恒定的电流,测量有机电致发光器件的亮度降为4750cd/m2的时间,单位为小时。测定结果如表1所示。
表1:
从表1结果可以看出,本发明所述化合物C121同对比例1相比,其开启电压大幅下降,电流效率及寿命均有所改善;在本发明中,其它实施例均表现出更优的开启电压及寿命较优光电性能。
实施例10
本实施例中有机电致发光器件制备过程如下:
将涂布了ITO透明导电层的玻璃板在商用清洗剂中超声处理,在去离子水中冲洗,在丙酮:乙醇混合溶剂中超声除油,在洁净环境下烘烤至完全除去水份,用紫外光和臭氧清洗,并用低能阳离子束轰击表面;
把上述带有阳极的玻璃基片置于真空腔内,抽真空至<1×10-5,在上述阳极层膜上真空蒸镀HI-3作为空穴注入层,蒸镀速率为0.1nm/s,蒸镀膜厚为10nm;
在空穴注入层之上真空蒸镀HT-4作为器件的空穴传输层,蒸镀速率为0.1nm/s,蒸镀总膜厚为80nm;
在空穴传输层之上,真空蒸镀HT-14作为器件的电子阻挡层,蒸镀速率为0.1nm/s,蒸镀总膜厚为80nm;
在电子阻挡层之上真空蒸镀器件的发光层,发光层包括主体材料和染料材料,利用多源共蒸的方法,调节主体材料C215蒸镀速率为0.1nm/s,染料RPD-8蒸镀速率3%比例设定,蒸镀总膜厚为30nm;
在发光层之上真空蒸镀器件的电子传输层材料ET-46,50%的比例设定和ET-57,50%的比例设定,其蒸镀速率为0.1nm/s,蒸镀总膜厚为30nm
在电子传输层(ETL)上真空蒸镀厚度为0.5nm的LiF作为电子注入层,厚度为150nm的Al层作为器件的阴极。
实施例11
本实施例中有机电致发光器件制备过程与实施例10中相同,区别仅在于将化合物C215替换为化合物C223作为主体材料。
实施例12
本实施例中有机电致发光器件制备过程与实施例10中相同,区别仅在于将化合物C215替换为化合物C245作为主体材料。
实施例13
本实施例中有机电致发光器件制备过程与实施例10中相同,区别仅在于将化合物C215替换为化合物C271作为主体材料。
实施例14
本实施例中有机电致发光器件制备过程与实施例10中相同,区别仅在于将化合物C215替换为化合物C278作为主体材料。
实施例15
本实施例中有机电致发光器件制备过程与实施例10中相同,区别仅在于将化合物C215替换为化合物C283作为主体材料。
实施例16
本实施例中有机电致发光器件制备过程与实施例10中相同,区别仅在于将化合物C215替换为化合物C301作为主体材料。
实施例17
本实施例中有机电致发光器件制备过程与实施例10中相同,区别仅在于将化合物C215替换为化合物C306作为主体材料。
对比例2
在该对比例中,有机电致发光器件制备过程与实施例10中相同,区别仅在于,将化合物C215替换为现有技术中的化合物I(b)作为主体材料,所述的I(b)结构如下。
对实施例10-14和对比例2制备的有机电致发光器件进行如下性能测定:
在同样亮度下,使用数字源表及亮度计测定实施例10-14和对比例2制备得到的有机电致发光器件的驱动电压和电流效率以及器件的寿命。具体而言,以每秒0.1V的速率提升电压,测定当有机电致发光器件的亮度达到5000cd/m2时的电压即驱动电压,同时测出此时的电流密度;亮度与电流密度的比值即为电流效率;LT95的寿命测试如下:使用亮度计在5000cd/m2亮度下,保持恒定的电流,测量有机电致发光器件的亮度降为4750cd/m2的时间,单位为小时。测定结果如表1所示。
表2:
从表2结果可以看出,本发明所述化合物C215同对比例2比较具有更低启动电压,更优的电流效率及寿命;本发明中,其它实施例均表现出更优的开启电压及寿命。
从上述结果可知,上述化合物作为发光层主体材料制备的器件具有启动电压低、性能高、寿命长的特点,这可能归结于本专利所设计的材料同对比材料相比较具有更好的空间堆积形态,这种堆积既能改善薄膜激子传输性能、又能获得更稳定的薄膜形态,有利于材料的稳定性提高,总而言之,该类材料是性能良好的主体材料。
尽管结合实施例对本发明进行了说明,但本发明并不局限于上述实施例,应当理解,在本发明构思的引导下,本领域技术人员可进行各种修改和改进,所附权利要求概括了本发明的范围。
显然,上述实施例仅仅是为清楚地说明所作的举例,而并非对实施方式的限定。对于所属领域的普通技术人员来说,在上述说明的基础上还可以做出其它不同形式的变化或变动。这里无需也无法对所有的实施方式予以穷举。而由此所引伸出的显而易见的变化或变动仍处于本发明创造的保护范围之中。
Claims (9)
1.一种通式化合物,如下式(1)所示:
其中:L1选自单键、取代或未取代的C6~C30的亚芳基、取代或未取代的C3~C30亚杂芳基中的一种;
Ar1选自取代或未取代的C6~C30芳基、取代或未取代的C3~C30的杂芳基中的一种;
X1~X14分别独立地为CR1,所述R1独立地选自氢、C1~C12烷基、C3~C12环烷基、C1~C12烷氧基、卤素、氰基、硝基、羟基、硅烷基、氨基、取代或未取代的C6~C30芳基氨基、取代或未取代的C3~C30杂芳基氨基、取代或未取代的C6~C30芳基、取代或未取代的C3~C30杂芳基中的一种;
当上述基团存在取代基时,所述取代基选自C1-C10的烷基、C3-C10的环烷基、C2-C10烯基、C1-C6的烷氧基或硫代烷氧基、C6-C30的单环芳烃或稠环芳烃基团、C3-C30的单环杂芳烃或稠环杂芳烃基团中的一种或者至少两种的组合。
2.根据权利要求1所述的通式化合物,式(1)中,L1为单键。
3.根据权利要求1或2所述的通式化合物,式(1)中,所述Ar1选自取代或未取代的C6~C30芳基、取代或未取代的C2~C30的吸电子杂芳基中的一种。
4.根据权利要求1或2所述的通式化合物,式(1)中,所述Ar1选自取代或未取代的下述基团:苯基、萘基、联苯基、三联苯基、三亚苯基、芴基、咔唑基、菲基、二苯并呋喃基、二苯并噻吩基、吡啶基、嘧啶基、三嗪基、喹啉基、喹唑啉基、喹喔啉基、菲咯啉基中的一种或多种的组合。
5.根据权利要求1-4中任一所述的通式化合物,式(1)中,所述X7和X8分别为的CR1中,R1独立地选自取代或未取代的C6~C30芳基、取代或未取代的C3~C30供电子杂芳基中的一种。
6.根据权利要求1-4中任一所述的通式化合物,式(1)中,所述X7和X8分别为的CR1中,R1选自取代或未取代的下述基团:芳胺基、苯基、萘基、联苯基、三联苯基、三亚苯基、芴基、咔唑基、菲基、二苯并呋喃基、二苯并噻吩基中的一种。
8.权利要求1-7中任一所述的化合物的应用,所述应用为在有机电致发光器件中作为发光层主体材料。
9.一种有机电致发光器件,该器件包括第一电极、第二电极和插入所述第一电极和第二电极之间的一层或多层有机层,其特征在于,所述有机层中包括至少一种由权利要求1-7中任一所述的化合物。
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