CN113620819A - 一种含杂原子稠环胺化合物和应用 - Google Patents

一种含杂原子稠环胺化合物和应用 Download PDF

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CN113620819A
CN113620819A CN202111050632.5A CN202111050632A CN113620819A CN 113620819 A CN113620819 A CN 113620819A CN 202111050632 A CN202111050632 A CN 202111050632A CN 113620819 A CN113620819 A CN 113620819A
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formula
compound
substituted
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hydrogen
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马晓宇
汪康
张鹤
唐志杰
刘萍
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Olide Shanghai Photoelectric Material Technology Co ltd
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Olide Shanghai Photoelectric Material Technology Co ltd
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Abstract

本发明提供了一种式(I)结构的含杂原子稠环胺化合物，本发明特定的发光辅助材料的存在使得从阳极转移的空穴能够平稳地移动到发光层，减少空穴传输层与发光层之间的势垒，降低器件的驱动电压；玻璃化转变温度得到了显著提高；进一步增加空穴的利用率，提高器件的发光效率和寿命。

Description

一种含杂原子稠环胺化合物和应用
技术领域
本发明涉及有机发光材料技术领域，尤其是涉及一种含杂原子稠环胺化合物和应用。
背景技术
有机电致发光(OLED:Organic Light Emission Diodes)器件技术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，有望替代现有的液晶显示和荧光灯照明，应用前景十分广泛。利用有机发光现象的有机电气元件通常具有阳极、阴极及它们之间包括有机物层的结构。为了提高有机电气元件的效率和稳定性，有机物层通常由各种不同物质构成的多层结构组成，
应用于OLED器件的OLED光电功能材料从用途上可划分为两大类，分别为电荷注入传输材料和发光材料。进一步，还可将电荷注入传输材料分为电子注入传输材料、电子阻挡材料、空穴注入传输材料和空穴阻挡材料，还可以将发光材料分为主体发光材料和掺杂材料。
空穴传输层(HTL)负责调节空穴的注入速度和注入量，在所述OLED中，酞菁铜(CuPc)、4，4’-双[N-(1-萘基)-N-苯基氨基]联苯(NPB)、N，N’-二苯基-N，N’-双(3-甲基苯基)-(1，1’-联苯基)-4，4’-二胺(TPD)、4，4’，4”-三(3-甲基苯基苯基氨基)三苯胺(MTDATA)等常用作在空穴传输区域中包含的化合物。然而，使用这些材料的OLED在使量子效率和使用寿命恶化方面存在问题。这是因为当在高电流下驱动OLED时，在阳极与空穴注入层之间出现热应力，并且所述热应力显著降低装置的使用寿命。此外，由于空穴传输区域中使用的有机材料具有非常高的空穴迁移率，所以可能破坏空穴-电子电荷平衡并且量子效率(cd/A)可能降低。
通常会在空穴输送层和发光层之间加入发光辅助层(多层空穴输送层)提高器件寿命和效率。发光辅助层能够起到减少空穴传输层与发光层之间的势垒，降低有机电致发光器件的驱动电压的作用，进一步增加空穴的利用率，从而改善器件的发光效率和寿命。开发更高性能的有机功能材料，满足面板制造企业的要求，显得尤为重要。
发明内容
有鉴于此，本发明要解决的技术问题在于提供一种含杂原子稠环胺化合物，本发明提供的化合物制备得到的有机电致发光器件具有较高的发光效率以及较长的寿命。
本发明提供了一种式(I)结构的含杂原子稠环胺化合物，
Figure BDA0003252824160000021
其中，X为-O-、-S-、-C(R5)(R6)-或-N(R7)-；R5，R6独立的选自甲基、乙基、苯基、甲基苯、联苯基、萘基或环戊基；R7选自苯基、甲基苯、联苯基、环戊基、萘基或三联苯基；
X1为C–Ra或N；X2为C–Rb或N；X2为C–Rc或N；X3为C–Rd或N；X4为C–Re或N；X5为C–Rf或N；X6为C–Rg或N；X7为C–Rh或N；X8为C–Ri或N；所述Ra、Rb、Rc、Rd、Re、Rf、Rg、Rh、Ri独立的选自氢、氘、C1～C10烷基、式II所示的A结构、取代或未取代的C6～C24亚芳基、含有一个或多个杂原子取代或未取代的环碳原子数为2～18亚杂芳基中的一种；所述杂原子选自O、N或S；或者Ra～Ri中任意两个相邻的基团与他们所在的C形成含取代基或不含取代基的苯环；
本发明所述X1～X8中N所在环上的位置优选为X2、X3、X5或X8；N个数为0～3；具体可以为0、1、2或3。
Ra～Ri至少一个为通式II所示结构；所述Ra～Ri最多为3个通式II所示结构。
式(II)中：
L1，L2，L3，Ar1，Ar2独立的选自氢，取代或未取代的C3～C8环烷基，取代或未取代的C6～C20亚芳基、含有一个或多个杂原子取代或未取代的环碳原子数为2～18亚杂芳基中的一种，所述杂原子选自O、N或S。
进一步优选的，所述L1，L2，L3，Ar1，Ar2独立的选自氢、环戊基、环己基、芳氧基、苯基、甲基苯、联苯基、萘基、三联苯基、芴基、二甲基芴、二苯基芴基、苯并噻吩基、苯并呋喃基、二苯并噻吩基、二苯并呋喃基或咔唑基；
L2，Ar1中至少有一个不为氢；
L3，Ar3中至少有一个不为氢。
特别优选的，所述Ra～Ri独立的选自氢、氘、甲基、乙基、丙基、异丙基、叔丁基、环戊基、环己基、烷氧基、苯基、甲基苯、联苯基、萘基、三联苯基、氟、氰基、丁基、戊基、己基、二苯并呋喃基、二苯并噻吩基、菲基、咔唑基或式II。
最优选的，本发明通式II所示结构选自如下结构：
Figure BDA0003252824160000031
Figure BDA0003252824160000041
Ra～Ri分别通过单键或形成苯并结构与所在环上任意位置相连；
Ar1，Ar2之间可以独立存在也可以相互键和成环。
本发明所述式(I)结构化合物为式(I-1)～式(I-14)所示结构：
Figure BDA0003252824160000042
其中，
X为-O-、-S-、-C(R5)(R6)-或-N(R7)-；R5，R6独立的选自甲基、乙基、苯基、甲基苯、联苯基、萘基或环戊基；R7选自苯基、甲基苯、联苯基、环戊基、萘基或三联苯基；
R1，R2，R3，R4独立的选自氢、氘、C1～C10烷基、式II所示的A结构、取代或未取代的C6～C24亚芳基、含有一个或多个杂原子取代或未取代的环碳原子数为2～18亚杂芳基中的一种；所述杂原子选自O、N或S；
R1，R2，R3，R4优选范围与Ra～Ri一致，在此不再赘述。
进一步，式(1)-式(5)中的R1，R2，R3，R4至少含有一个式II所示结构；本发明上述已经对式II所示结构进行了清楚的描述，在此不再赘述。
R1，R2，R3，R4中，非式II所示结构的R优选为取代基氢，氘，甲基，苯基，叔丁基，甲基苯基，甲氧烷基，联苯基、萘基；
Figure BDA0003252824160000051
X，X1-X8，R1，R2，R3，R4与上述选取范围相同；在此不再赘述。
进一步，X1-X8中，杂原子个数优选为1-3，杂原子优选为N；
式(6)-式(10)每个式中的R1，R2，R3，R4至少含有一个式II所示结构；本发明上述已经对式II所示结构进行了清楚的描述，在此不再赘述。
R1，R2，R3，R4中，非式II所示结构的R优选为取代基氢，氘，甲基，苯基，叔丁基，甲基苯基，甲氧烷基，联苯基、萘基；
Figure BDA0003252824160000052
Figure BDA0003252824160000061
X，X5-X8，R1，R2，R3，R4与上述选取范围相同；在此不再赘述。
进一步，X5-X8中，杂原子个数为1-3，杂原子优选为N；
式(I-1)-式(I-14)式中的R1，R2，R3，R4至少含有一个式II所示结构；本发明上述已经对式II所示结构进行了清楚的描述，在此不再赘述。
同时，式(I-1)～式(I-5)中，R1、R2、R3、R4至少有两个不为氢。
本申请中的术语“取代或未取代”中的取代是指包括被选自以下至少一个取代基取代：氘、卤素基团、腈基、羟基、羰基、酯基、甲硅烷基、硼基、经取代或未取代的烷基、经取代或未取代的环烷基、经取代或未取代的烷氧基、经取代或未取代的烯基、经取代或未取代的烷基胺基、经取代或未取代的杂环基胺基、经取代或未取代的芳基胺基、经取代或未取代的芳基、和经取代或未取代的杂环基，或者被以上所示的取代基中的两个或更多个取代基相连接的取代基取代。术语“取代或未取代”中的未经取代是指不具有取代基。
按照本发明，所述式(Ⅰ)结构化合物优选具有以下任一结构：
Figure BDA0003252824160000062
Figure BDA0003252824160000071
Figure BDA0003252824160000081
Figure BDA0003252824160000091
Figure BDA0003252824160000101
Figure BDA0003252824160000111
Figure BDA0003252824160000121
本发明对于制备方法不进行限定，本领域技术人员熟知的能够合成上述化合物的方法即可。
本发明合成路线优选如下：
1、当X＝-C(R5)(R6)-时，采用本领域技术人员熟知的格式反应，合环反应，Buchwald–Hartwig偶联反应得到目标化合物。
2、当X＝O、S时，采用本领域技术人员熟知的铃木反应，合环反应，Buchwald–Hartwig偶联反应得到目标化合物。
3、当X＝-N(R7)-时，采用本领域技术人员熟知的Buchwald–Hartwig偶联反应得到目标化合物。
本发明提供了一种含杂原子稠环胺化合物及其制备方法以及以该材料为发光辅助层或空穴传输材料的有机电致发光器件。本发明化合物含杂原子稠环，以及芳胺衍生物为核心，具有较高的玻璃化温度，通过器件结构优化，可有效提升OLED器件的寿命和发光效率。
本发明提供了一种发光辅助层材料，包括上述技术方案任意一项所述的式(Ⅰ)结构的化合物。
本发明所述化合物优选作为发光辅助层材料。
本发明提供了一种有机电致发光器件，其包括第一电极、第二电极和置于所述第一电极和第二电极之间的一个或多个有机化合物层，其中至少一个有机化合物层包含上述技术方案任意一项所述的化合物。
本发明所述一个或多个有机化合物层包括空穴注入层、空穴传输层、发光辅助层、电子阻挡层、发光层、空穴阻挡层、电子传输层和电子注入层中的至少一层或多层。
本发明中，第一电极作为阳极，阳极优选包含具有高逸出功的材料。例如氧化锡铟(ITO)或氧化铟锌(IZO)。
由于在水和/或空气存在下本发明器件的寿命会缩短，因此所述器件被适当地(取决于应用)结构化、提供接点并最后密封。
空穴传输材料是具有高空穴迁移率的材料，其能够接收来自阳极或空穴注入层的空穴并将空穴传输至发光层。其具体实例包括基于芳基胺的有机材料、导电聚合物、同时具有共轭部分和非共轭部分的嵌段共聚物等。
当所述有机物层包括发光辅助层时，所述发光辅助层可包括通式I所示的化合物。
发光层的材料是一种通过分别接收来自空穴传输层和电子传输层的空穴和电子，并将所接收的空穴和电子结合而能发出可见光的材料。此外，发光层可以包含主体材料和掺杂材料；主体材料和掺杂材料的质量比为90-99.5:0.5-10；掺杂材料可以包括荧光掺杂和磷光掺杂。
空穴阻挡层材料，可以使用现有技术中公知的具有空穴阻挡作用的化合物，例如，浴铜灵(BCP)等菲咯啉衍生物、噁唑衍生物、三唑衍生物、三嗪衍生物等，但不限于此。
电子传输层可以起到促进电子传输的作用。可以使用现有技术中公知的具有电子传输作用的化合物，例如，8-羟基喹啉的Al配合物；包含Alq3的配合物；有机自由基化合物；羟基黄酮-金属配合物等。
电子注入层可以起到促进电子注入的作用。具有传输电子的能力，防止发光层中产生的激子迁移至空穴注入层。本发明中使用的电子注入材料包括芴酮、蒽醌二甲烷、联苯醌、噻喃二氧化物、唑、二唑、三唑、咪唑、苝四羧酸、亚芴基甲烷或蒽酮，以及其衍生物、金属配合物或含氮五元环衍生物等，但不限于此。
本发明中，第二电极作为阴极，通常优选具有小功函数的材料以便电子顺利注入有机材料层。例如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅，或其合金。该层的层厚度优选在0.5和2nm之间。
本发明还提供了一种有机电致发光器件，包括以上有机发光化合物或上述制备方法制备的有机发光化合物；所述有机电致发光器件为本领域技术人员熟知的有机电致发光器件即可。
与现有技术相比，本发明提供了一种式(I)结构的含杂原子稠环胺化合物，本发明特定的发光辅助材料的存在使得从阳极转移的空穴能够平稳地移动到发光层，减少空穴传输层与发光层之间的势垒，降低器件的驱动电压；玻璃化转变温度得到了显著提高；进一步增加空穴的利用率，提高器件的发光效率和寿命。
具体实施方式
本发明提供了一种含杂原子稠环胺化合物和应用，本领域技术人员可以借鉴本文内容，适当改进工艺参数实现。特别需要指出的是，所有类似的替换和改动对本领域技术人员来说是显而易见的，它们都属于本发明保护的范围。本发明的方法及应用已经通过较佳实施例进行了描述，相关人员明显能在不脱离本发明内容、精神和范围内对本文的方法和应用进行改动或适当变更与组合，来实现和应用本发明技术。
为了进一步说明本发明，以下结合实施例对本发明提供的一种含杂原子稠环胺化合物和应用进行详细描述。
实施例1：化学式1的合成
Figure BDA0003252824160000151
步骤1：将化合物A-1(50mmol)与的THF(500mL)混合，并加入Me-Mg-Br(55mmol)。在60℃下搅拌12小时后，将反应溶液在室温下缓慢加入蒸馏水中。用丙烯酸乙酯萃取并经硫酸镁干燥。柱分离得到反应物B-1(16.2g，Ms:391.31，产率：83％)；
步骤2：将中间体B-1(40mmol)加入三口瓶中，加入冰醋酸，加热至120℃，滴加浓硫酸，搅拌5min；冷却至室温，加入碳酸氢钠溶液终止反应，分液，水相用二氯甲烷萃取三次，收集有机相，加入无水硫酸镁干燥，通过旋转蒸发仪除去溶剂，得到中间体C-1(12.8g，Ms:372.05，产率：86％)；
步骤3：在反应容器中加入中间体C-1(30mmol)和反应物D-1(36mmol)溶于500ml甲苯之后，在氮气氛围下加入Pd2(dba)3(0.3mmol)、P(t-Bu)3(1.8mmol)、t-BuONa(72mmol)。添加后，使反应温度缓慢升温到110℃，并且搅拌混合物10h。使用硅藻土趁热抽滤，除去盐和催化剂，滤液冷却至室温后，接着将蒸馏水添加到滤液中进行洗涤，分液后保留有机相，用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层，并且使用旋转式蒸发器去除溶剂。以二氯甲烷：石油醚体积比为1:(1-9)作为洗脱剂，用管柱色谱法纯化剩余物质，获得化合物1(15.9g，产率为81％)。
质谱测试：理论值为653.87；测试值为653.46。
元素分析：
理论值：C,91.85；H,6.01；N,2.14
测试值：C,91.86；H,6.00；N,2.15
实施例2：化学式58的合成
Figure BDA0003252824160000161
步骤1：N2保护下，将反应物A-58(50mmol)、反应物B-58(55mmol)、四(三苯基膦)钯(0.5mmol)和碳酸钾(110mmol)分别加入到400mL甲苯、150mL乙醇、150mL水的混合溶剂中，升温至100℃回流反应8h，反应结束后，冷却至室温，待固体析出完毕后，抽滤后用水洗涤除去盐，再用少量乙醇淋洗，干燥滤饼。置于1,4-二氧六环中重结晶，得到中间体C-58(13.7g，Ms:333.09，82％)；
步骤2：在-10℃下搅拌中间体C-58(40mmol)、四氢呋喃(120mL，THF)、和160mL冰醋酸(HOAc)的混合物，在10min内滴加(CH3)3CONO(亚硝酸叔丁酯)(120mmol)。将反应混合物在-10℃搅拌2小时，然后缓慢升温至室温，反应5小时。反应完成后，加入700mL水稀释。粗沉淀物通过硅胶上的柱色谱法纯化，得到中间体D-58(8.5g，Ms：302.76，产率：70％)；
步骤3：在反应容器中加入中间体D-58(25mmol)和反应物E-58(27.5mmol)溶于100ml甲苯之后，在氮气氛围下加入Pd2(dba)3(0.25mmol)、P(t-Bu)3(13.8mmol)、t-BuONa(55mmol)。添加后，使反应温度缓慢升温到110℃，并且搅拌混合物10h。使用硅藻土趁热抽滤，除去盐和催化剂，滤液冷却至室温后，接着将蒸馏水添加到滤液中进行洗涤，分液后保留有机相，用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层，并且使用旋转式蒸发器去除溶剂。以二氯甲烷：石油醚体积比为1:(1-9)作为洗脱剂，用管柱色谱法纯化剩余物质，获得化合物58(18.6g，产率为80％)。
质谱测试：理论值为663.26；测试值为663.51。
元素分析：
理论值：C,90.47；H,5.01；N,2.11；O,2.41
测试值：C,90.45；H,5.01；N,2.12；O,2.42
实施例3：化学式67的合成
Figure BDA0003252824160000171
步骤1：在反应容器中加入中间体C-67(50mmol)和反应物D-67(60mmol)溶于500ml甲苯之后，在氮气氛围下加入Pd2(dba)3(0.5mmol)、P(t-Bu)3(3mmol)、t-BuONa(100mmol)。添加后，使反应温度缓慢升温到110℃，并且搅拌混合物10h。使用硅藻土趁热抽滤，除去盐和催化剂，滤液冷却至室温后，接着将蒸馏水添加到滤液中进行洗涤，分液后保留有机相，用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层，并且使用旋转式蒸发器去除溶剂。以二氯甲烷：石油醚体积比为1:(1-9)作为洗脱剂，用管柱色谱法纯化剩余物质，获得化合物67(28.7g，产率为80％)。
质谱测试：理论值为716.28；测试值为716.35。
元素分析：
理论值：C,88.80；H,5.06；N,3.91；O,2.23
测试值：C,88.80；H,5.08；N,3.90；O,2.21
实施例4：化学式84的合成
Figure BDA0003252824160000181
步骤1：N2保护下，将反应物A-84(50mmol)、反应物B-84(55mmol)、四(三苯基膦)钯(0.5mmol)和碳酸钾(110mmol)分别加入到400mL甲苯、150mL乙醇、150mL水的混合溶剂中，升温至100℃回流反应8h，反应结束后，冷却至室温，待固体析出完毕后，抽滤后用水洗涤除去盐，再用少量乙醇淋洗，干燥滤饼。置于1,4-二氧六环中重结晶，得到中间体C-84(16.6g，Ms:410.90，81％)；
步骤2：在-10℃下搅拌中间体C-84(40mmol)、四氢呋喃(120mL，THF)、和160mL冰醋酸(HOAc)的混合物，在10min内滴加(CH3)3CONO(亚硝酸叔丁酯)(120mmol)。将反应混合物在-10℃搅拌2小时，然后缓慢升温至室温，反应5小时。反应完成后，加入700mL水稀释。粗沉淀物通过硅胶上的柱色谱法纯化，得到中间体D-84(10.6g，Ms：379.08，产率：75％)；
步骤3：在反应容器中加入中间体D-84(25mmol)和反应物E-84(27.5mmol)溶于100ml甲苯之后，在氮气氛围下加入Pd2(dba)3(0.25mmol)、P(t-Bu)3(13.8mmol)、t-BuONa(55mmol)。添加后，使反应温度缓慢升温到110℃，并且搅拌混合物10h。使用硅藻土趁热抽滤，除去盐和催化剂，滤液冷却至室温后，接着将蒸馏水添加到滤液中进行洗涤，分液后保留有机相，用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层，并且使用旋转式蒸发器去除溶剂。以二氯甲烷：石油醚体积比为1:(1-9)作为洗脱剂，用管柱色谱法纯化剩余物质，获得化合物84(14.5g，产率为84％)。
质谱测试：理论值为688.25；测试值为688.72。
元素分析：
理论值：C,88.93；H,4.68；N,4.07；O,2.32
测试值：C,88.94；H,4.69；N,4.07；O,2.30
实施例5：化学式124的合成
Figure BDA0003252824160000191
步骤1：将化合物A-124(50mmol)与的THF(500mL)混合，并加入Me-Mg-Br(55mmol)(144.26mmol，乙醚中的3.0M)。在60℃下搅拌12小时后，将反应溶液在室温下缓慢加入蒸馏水中。用丙烯酸乙酯萃取并经硫酸镁干燥。柱分离得到反应物B-124(18.0g，Ms:440.08，产率：82％)；
步骤2：将中间体B-124(40mmol)加入三口瓶中，加入冰醋酸，加热至120℃，滴加浓硫酸，搅拌5min；冷却至室温，加入碳酸氢钠溶液终止反应，分液，水相用二氯甲烷萃取三次，收集有机相，加入无水硫酸镁干燥，通过旋转蒸发仪除去溶剂，得到中间体C-124(14.0g，Ms:422.07，产率：83％)；
步骤3：在反应容器中加入中间体C-124(30mmol)和反应物D-124(36mmol)溶于500ml甲苯之后，在氮气氛围下加入Pd2(dba)3(0.3mmol)、P(t-Bu)3(1.8mmol)、t-BuONa(72mmol)。添加后，使反应温度缓慢升温到110℃，并且搅拌混合物10h。使用硅藻土趁热抽滤，除去盐和催化剂，滤液冷却至室温后，接着将蒸馏水添加到滤液中进行洗涤，分液后保留有机相，用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层，并且使用旋转式蒸发器去除溶剂。以二氯甲烷：石油醚体积比为1:(1-9)作为洗脱剂，用管柱色谱法纯化剩余物质，获得化合物124(16.5g，产率为73％)。
质谱测试：理论值为753.34；测试值为753.58。
元素分析：
理论值：C,92.39；H,5.75；N,1.86
测试值：C,92.37；H,5.76；N,1.87
实施例6至实施例18
参照实施例1至5的合成方法完成对化合物18，23，36，48，60，70，78，90，95，100，105，120，128的合成，质谱、分子式以及产率如表1。
表1：
Figure BDA0003252824160000201
Figure BDA0003252824160000211
[器件应用例1]作为发光辅助材料制备的有机电致发光器件：
将费希尔公司涂层厚度为150nm的ITO玻璃基板放在蒸馏水中清洗2次，超声波洗涤30min，用蒸馏水反复清洗2次，超声波洗涤10min，蒸馏水清洗结束后，异丙醇、丙酮、甲醇等溶剂按顺序超声波洗涤以后干燥，转移到等离子体清洗机里，将上述基板洗涤5min，送到蒸镀机里。将化合物HT以及P-dopant(3％)引入真空气相沉积设备的小室中，将所述设备的腔室中的压力控制到10-6托。此后，向小室施加电流以使以上引入的材料蒸发，从而在ITO基板上形成具有10nm厚度的空穴注入层。在形成的空穴注入层上面真空蒸镀厚度为35nm的HT为空穴传输层，在上述空穴输送层上以20nm的厚度真空沉积本发明的化合物1来形成发光辅助层后制作OLED发光器件的发光层，其结构包括OLED发光层所使用Host作为主体材料，Dopant作为掺杂材料，掺杂材料掺杂比例为3％重量比，发光层膜厚为40nm。
在上述发光层上真空蒸镀厚度为12nmTPBi作为空穴阻挡层，在上述空穴阻挡层上以40nm的厚度真空沉积ET作为电子传输层；在上述电子传输层上真空蒸镀厚度为1.0nm羟基喹啉锂(Liq)，作为电子注入层。在电子注入层上，制作膜厚为150nm的Al电极层，此层为阴极层使用。
器件结构：
ITO/HT:p-dopant/HT/化合物1/Host:Dopant/TPBi/ET/Liq/Al。
如上所述地完成OLED发光器件后，用公知的驱动电路将阳极和阴极连接起来，测量器件的电流效率以及器件的寿命。按照上述步骤完成电致发光器件的制作后，测量器件的驱动电压，发光效率和寿命。
相关材料的分子结构式如下所示：
Figure BDA0003252824160000221
[器件应用例2]-[器件应用例136]
参照上述方法，将器件应用例1中使用的化合物1分别替换为式I中化合物2-136作为发光辅助层，制备得到相应的有机电致发光器件。
[器件对比例1]-[器件对比例4]
参照上述方法，将器件应用例1中使用的化合物1分别替换为对比化合物1、对比化合物2、对比化合物3，对比化合物4作为发光辅助层，制备得到相应的有机电致发光器件。
Figure BDA0003252824160000231
对上述制备的有机电致发光器件加以正向直流偏置电压，利用Photo Research公司的PR-650光度测量设备测定有机电致发光特性，亮度为6000cd/m2下利用McScience公司的寿命测定装置测定了T95的寿命。结果见表2。
表2器件应用例1～136以及器件对比例1～4制备的有机电致发光器件的发光特性测试结果(亮度值为6000cd/m2)
Figure BDA0003252824160000232
Figure BDA0003252824160000241
Figure BDA0003252824160000251
Figure BDA0003252824160000261
Figure BDA0003252824160000271
Figure BDA0003252824160000281
从表2可以看出，
器件性能显示，器件实施例1-器件实施例136与对比例1-4相比，在寿命，发光效率，玻璃化器件性能有显著提高。
驱动电压主要受主体影响，主体一致的情况下，驱动电压略有降低，在0.1-0.3V。
以上所述仅是本发明的优选实施方式，应当指出，对于本技术领域的普通技术人员来说，在不脱离本发明原理的前提下，还可以做出若干改进和润饰，这些改进和润饰也应视为本发明的保护范围。

Claims (9)

1.一种式(I)结构的含杂原子稠环胺化合物，
Figure FDA0003252824150000011
其中，X为-O-、-S-、-C(R5)(R6)-或-N(R7)-；R5，R6独立的选自甲基、乙基、苯基、甲基苯、联苯基、萘基或环戊基；R7选自苯基、甲基苯、联苯基、环戊基、萘基或三联苯基；
X1为C–Ra或N；X2为C–Rb或N；X2为C–Rc或N；X3为C–Rd或N；X4为C–Re或N；X5为C–Rf或N；X6为C–Rg或N；X7为C–Rh或N；X8为C–Ri或N；所述Ra、Rb、Rc、Rd、Re、Rf、Rg、Rh、Ri独立的选自氢、氘、C1～C10烷基、式II所示的A结构、取代或未取代的C6～C24亚芳基、含有一个或多个杂原子取代或未取代的环碳原子数为2～18亚杂芳基中的一种；所述杂原子选自O、N或S；或者Ra～Ri中任意两个相邻的基团与他们所在的C形成含取代基或不含取代基的苯环；所述取代基选自氢、氘、C1～C10烷基、式II所示的A结构、取代或未取代的C6～C24亚芳基、含有一个或多个杂原子取代或未取代的环碳原子数为2～18亚杂芳基中的一种；
Ra～Ri至少一个为通式II所示结构；
L1，L2，L3，Ar1，Ar2独立的选自氢，取代或未取代的C3～C8环烷基，取代或未取代的C6～C20亚芳基、含有一个或多个杂原子取代或未取代的环碳原子数为2～18亚杂芳基中的一种，所述杂原子选自O、N或S。
2.根据权利要求1所述的化合物，其特征在于，所述X1～X8中N所在环上的位置为X2、X3、X5或X8；N个数为0～3；
所述Ra～Ri最多为3个通式II所示结构。
3.根据权利要求1所述的化合物，其特征在于，所述L1，L2，L3，Ar1，Ar2独立的选自氢、环戊基、环己基、芳氧基、苯基、甲基苯、联苯基、萘基、三联苯基、芴基、二甲基芴、二苯基芴基、苯并噻吩基、苯并呋喃基、二苯并噻吩基、二苯并呋喃基或咔唑基；
L2，Ar1中至少有一个不为氢；
L3，Ar3中至少有一个不为氢。
4.根据权利要求1所述的化合物，其特征在于，所述Ra～Ri独立的选自氢、氘、甲基、乙基、丙基、异丙基、叔丁基、环戊基、环己基、烷氧基、苯基、甲基苯、联苯基、萘基、三联苯基、氟、氰基、丁基、戊基、己基、二苯并呋喃基、二苯并噻吩基、菲基、咔唑基或式II。
5.根据权利要求4所述的化合物，其特征在于，式II的结构具体为如下结构：
Figure FDA0003252824150000021
Figure FDA0003252824150000031
6.根据权利要求1所述的化合物，其特征在于，所述式(I)结构化合物为式(I-1)～式(I-14)所示结构：
Figure FDA0003252824150000032
Figure FDA0003252824150000041
其中，R1、R2、R3、R4独立的选自氢、氘、C1～C10烷基、式II所示的A结构、取代或未取代的C6～C24亚芳基、含有一个或多个杂原子取代或未取代的环碳原子数为2～18亚杂芳基中的一种；所述杂原子选自O、N或S；R1、R2、R3、R4至少一个为通式II所示结构；且式(I-1)～式(I-5)中，R1、R2、R3、R4至少有两个不为氢。
7.根据权利要求6所述的化合物，其特征在于，所述式(Ⅰ)结构化合物具有以下任一结构：
Figure FDA0003252824150000042
Figure FDA0003252824150000051
Figure FDA0003252824150000061
Figure FDA0003252824150000071
Figure FDA0003252824150000081
Figure FDA0003252824150000091
Figure FDA0003252824150000101
8.一种发光辅助层材料，其特征在于，包括权利要求1～7任意一项所述的式(Ⅰ)结构的化合物。
9.一种有机电致发光器件，其包括第一电极、第二电极和置于所述第一电极和第二电极之间的一个或多个有机化合物层，其中至少一个有机化合物层包含权利要求1～7任意一项所述的化合物。
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