CN112430217B - 一种化合物及其应用 - Google Patents
一种化合物及其应用 Download PDFInfo
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- CN112430217B CN112430217B CN201910792518.6A CN201910792518A CN112430217B CN 112430217 B CN112430217 B CN 112430217B CN 201910792518 A CN201910792518 A CN 201910792518A CN 112430217 B CN112430217 B CN 112430217B
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- 239000012074 organic phase Substances 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 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
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 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
本发明涉及一种化合物及其应用,所述化合物具有式(1)所示的结构;所述化合物应用于有机电致发光器件;所述有机电致发光器件包括第一电极、第二电极以及位于第一电极和第二电极之间的有机层,所述有机层中含有式(1)所示的化合物。本发明通过特定的吸电与供电基团的搭配使用,使得分子整体的HOMO与LUMO能级与其他功能层相匹配,降低了载流子的传输壁垒,在通过引入高迁移率的杂芳基取代基团,使得本发明材料具备相比较已有材料,能够使器件具有更低的电压和更高的效率。
Description
技术领域
本发明涉及有机电致发光技术领域,特别涉及一种化合物及其应用。
背景技术
近几年来,有机发光二极管(OLED)发展十分迅猛,在信息显示领域占有一席之地,这主要得益于OLED器件可以利用高饱和度红绿蓝三原色制备全色显示装置,且无需额外的背光源,就能够实现色彩绚丽、轻薄柔软的性能。
OLED器件中起到重要作用的是含有多种有机功能材料的薄层结构,常见的有机功能材料包括发光层材料、电子阻挡层材料、电子传输层材料、空穴阻挡层材料、空穴传输层材料等。接通电源后,电子和空穴分别被注入、传输至发光层并在此复合产生激子,实现发光。因此,对于OLED器件中的有机功能材料的研究是本领域技术人员的重点研究课题。
目前,研究人员已开发出多种多样的有机功能材料以用于各种特定的器件结构,起到提升载流子迁移率、调控载流子平衡、突破电致发光效率、延缓器件衰减的作用。
常见的荧光发光体主要是利用空穴和电子复合时产生的单线态激子发光,这种发光体仍用于各种OLED器件中。此外,还包括磷光发光体,即一种可以同时利用三线态激子和单线态激子发光的材料,例如铱络合物等。最值得关注的是,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)技术就是采用TADF材料,通过能量转移的方式来敏化发光体,实现较高的发光效率,TADF材料在OLED领域有着广阔的应用前景。
虽然多种多样的有机功能层材料已经被开发,但是当今人们对于OLED器件性能的要求越来越高,现有的有机功能材料已经无法适用于更高性能的新型OLED器件。因此,本领域亟待开发更多种类的有机功能材料,使其应用于OLED器件时能够提高发光效率,降低驱动电压。
发明内容
本发明的目的在于提供一种化合物,所述化合物在平衡空穴与电子传输的同时,保持更佳的载流子传输速率,能够满足对OLED器件的光电性能不断提升的需求。
为达此目的,本发明采用以下技术方案:
本发明提供了一种化合物,所述化合物具有式(1)所示的结构;
式(1)中,所述X1和X2中一个为N,另一个为CR5;
所述R1、R2、R3、R4和R5各自独立的选自氢原子、取代或未取代的C1~C12烷基、取代或未取代的C3~C12环烷基、取代或未取代的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、取代或未取代的C3~C30杂芳基中的任意一种,所述R1、R2、R3、R4和R5中相邻的两个取代基之间稠合成环或不稠合成环;示例性地,R1和R2可以稠合成环,也可以为独立的两个取代基。
式(1)中,所述L1、L2和L3各自独立的选自单键、取代或未取代的C6~C30亚芳基、取代或未取代的C3~C30亚杂芳基中的任意一种;
式(1)中,所述Ar1和Ar2各自独立的选自取代或未取代的C6~C30芳基、取代或未取代的C3~C30杂芳基中的任意一种;
式(1)中,所述的Ar3选自如下基团中的任意一种:
所述Z1、Z2、Z3、Z4、Z5、Z6、Z7和Z8各自独立地选自N或CRc,且至少有一项为N;
所述m为1~5的整数,例如1、2、3、4、5,所述a为1~m的整数;
所述n为1~8的整数,例如1、2、3、4、5、6、7、8,所述b为1~n的整数;
所述s为1~7的整数,例如1、2、3、4、5、6、7,所述d为1~s的整数;
所述c为1~7的整数,例如1、2、3、4、5、6、7;
所述Ra、Rb、Rc和Rd各自独立地选自氢原子、卤素、氰基、C1~C12的烷基、C1~C12的烷氧基、C6~C30的芳基、C3~C30的杂芳基中的任意一种;
其中,虚线代表基团的连接位点;
当上述基团存在取代基时,所述取代基各自独立地选自氰基、卤素、C1~C10的烷基或环烷基、C2~C6的烯基、C1~C6的烷氧基或硫代烷氧基、硝基、氨基、羰基、羧基、酯基、C6~C30的单环芳基或稠环芳基、C3~C30的单环杂芳基或稠环杂芳基。
本发明中,Ra、Rb、Rc和Rd独立地代表一类基团,而非特定的一个基团,示例性地,当m为2时,a为1~2的整数,则a为1或2,即Ra可以是R1,也可以是R2,也就是说,当母环上取代有两个Ra时,这两个Ra可以相同,也可以不同。Rb、Rc和Rd同理。
本发明中,实线或虚线划过环的表示方法代表基团的接入位点可以为被划过的环上的任意可成键位置。
本发明材料是以均三苯为中心的母核结构,其中取代基团中必须含有一个2个氮原子的吸电基团(喹唑啉或喹喔啉),保证了分子结构LUMO能级,同时分子结构中必须含有一个芳胺基团,保证分子的HOMO能级,此外,在第三个取代基团中我们引入载流子传输性能良好的杂芳基(Ar3),这几类特定结构的杂芳基(Ar3)与喹唑啉或喹喔啉以及芳胺基团配合,使得分子在平衡空穴与电子传输的同时,保持更佳的载流子传输速率。
总而言之本发明化合物通过上述固定吸电与供电基团的搭配使用,使得分子整体的HOMO与LUMO能级与其他功能层相匹配,降低了载流子的传输壁垒,在通过引入高迁移率的杂芳基取代基团,使得本发明材料具备相比较已有材料,能够使器件具有更低的电压和更高的效率。
本发明中述取代或未取代的C1-C12烷基,优选C1-C10的烷基,更优选C1-C6的烷基,例如可举出:甲基、乙基、正丙基、异丙基、正丁基、正己基、正辛基、异丁基、叔丁基、环丙基、环丁基、环戊基、环己基等。
本发明中取代或未取代的C6-C30芳基,优选C6-C20芳基,优选所述芳基包括苯基、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;所述萘基包括1-萘基或2-萘基;所述蒽基选自1-蒽基、2-蒽基和9-蒽基;所述芴基选自由1-芴基、2-芴基、3-芴基、4-芴基和9-芴基;所述芴基衍生物选自9,9’-二甲基芴、9,9’-螺二芴和苯并芴;所述芘基选自1-芘基、2-芘基和4-芘基;所述并四苯基选自1-并四苯基、2-并四苯基和9-并四苯基。
本发明中,取代或未取代的C3-C30杂芳基,优选C6-C20杂芳基,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。
优选地,所述X1为CR5,X2为N。
优选地,所述Z1、Z2、Z3、Z4、Z5、Z6、Z7和Z8中有且仅有一项为N。
优选地,所述Ra、Rb、Rc和Rd各自独立地选自氢原子、苯基、氰基或甲氧基中的任意一种。
优选地,所述的Ar3选自如下基团中的任意一种:
所述Z1、Z2、Z3、Z4、Z5、Z6、Z7和Z8各自独立地选自N或CH,且所述Z1、Z2、Z3、Z4、Z5、Z6、Z7和Z8中有且仅有一项为N;
其中,Ph代表苯基,虚线代表基团的连接位点。
优选地,所述Ar3选自如下基团中的任意一种:
其中,虚线代表基团的连接位点。
优选地,所述Ar1和Ar2各自独立的选自苯基、萘基、二苯并噻吩基、联苯基或芴基中的任意一种。
优选地,所述L1、L2和L3各自独立的选自单键或者取代或未取代的C6~C30亚芳基;优选单键或C6~C30亚芳基;进一步优选单键或亚苯基。
优选地,所述化合物具有如下P1~P91所示的结构中的任意一种:
本发明的目的之二在于提供一种目的之一所述的化合物的应用,所述化合物应用于有机电致发光器件。
优选地,所述化合物用作所述有机电致发光器件中的发光层材料,优选用作发光层主体材料。
本发明的目的之三在于提供一种有机电致发光器件,所述有机电致发光器件包括第一电极、第二电极以及位于第一电极和第二电极之间的有机层,所述有机层中含有目的之一所述的化合物。
在一个具体实施方式中,所述有机层还可以包括空穴传输区、发光层、电子传输区。
在一个具体实施方式中,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。
空穴传输区的材料可以选自、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至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HI1至HI3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RPD-1至RPD-28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。
阴极为镁银混合物、LiF/Al、ITO等金属、金属混合物、氧化物。
相对于现有技术,本发明具有以下有益效果:
本发明材料是以均三苯为中心的母核结构,其中取代基团中必须含有一个2个氮原子的吸电基团,保证了分子结构LUMO能级,同时分子结构中必须含有一个芳胺基团,保证分子的HOMO能级,在第三个取代基团中我们引入载流子传输性能良好的杂芳基(Ar3),使得分子在平衡空穴与电子传输的同时,保持更佳的载流子传输速率。
总而言之本发明化合物通过上述固定吸电与供电基团的搭配使用,使得分子整体的HOMO与LUMO能级与其他功能层相匹配,降低了载流子的传输壁垒,在通过引入高迁移率的杂芳基取代基团,使得本发明材料具备相比较已有材料,能够使器件具有更低的电压和更高的效率。
具体实施方式
下面通过具体实施方式来进一步说明本发明的技术方案。本领域技术人员应该明了,所述实施例仅仅是帮助理解本发明,不应视为对本发明的具体限制。
本发明式(1)所示的化合物的代表合成方法如下:
其中,X为卤素,具体可选自氯、溴或者碘,-OTF为CF3SO3-。
上述第三步反应和第四步反应均为常见的Suzuki或者Buchwald-Hartwig偶联反应,根据L2、L3、Ar1、Ar2和Ar3的具体结构不同,可以选择不同的原料,具体可参见下文的合成例。
式(1)化合物的合成方法不限于上述方法,本领域技术人员还可以根据现有技术选择其他的合成方法,本发明对其不作限定。
更具体的,针对特定的取代基,还可以选择下述两种特定的合成方法:
方法1:
方法2:
本发明以下合成例中未提到的合成方法的化合物的都是通过商业途径获得的原料产品。本发明中所用溶剂和试剂,例如二氯甲烷、乙醇、喹唑啉、喹喔啉等化学试剂,均可以从国内化工产品市场购买,例如购买自国药集团试剂公司、TCI公司、上海毕得医药公司、百灵威试剂公司等。另外,本领域技术人员也可以通过公知方法合成。
合成例1
化合物P1的合成
将S1(30mmol)、2-氯-4-苯基喹唑啉(60mmol)、碳酸钾(45mmol)、二氧六环(200mL)、四(三苯基膦)钯(0.3mmol)、水50mL加入到反应瓶中,加热至回流反应3h,TLC监控反应完成,将反应液倒入水中过滤,二氯萃取后浓缩后甲苯重结晶得中间体A。
将A(15mmol)、二苯胺(16mmol)、叔丁醇钠(20mmol)、三(二亚苄基丙酮)二钯(0.15mmol)、三叔丁基膦(0.3mmol)、二甲苯200mL加入至反应瓶中,加热至120℃反应6h,TLC监控反应完全,降温后直接过滤,滤饼用二甲苯重结晶得到化合物P1。
合成例2:
化合物P9的合成
与合成例1的区别在于,将2-氯-4-苯基喹唑啉替换成等物质的量的2-氯-3-苯基喹喔啉,得到化合物P9。
合成例3:
化合物P17的合成
将S2(30mmol)、2-氯-4-苯基喹唑啉(60mmol)、碳酸钾(45mmol)、二氧六环(200mL)、四(三苯基膦)钯(0.3mmol)、水50mL加入到反应瓶中,加热至回流反应3h,TLC监控反应完成,将反应液倒入水中过滤,二氯萃取后浓缩后甲苯重结晶得中间体A。
将A(20mmol)、吡啶(40mmol)加入到200mL二氯甲烷中,降温至-5℃,滴加三氟甲磺酸酐(40mmol),滴加完毕后室温反应1h,TLC监控反应完全,加入水淬灭后二氯甲烷萃取浓缩得中间体B。
将B(15mmol)、二苯并噻吩-4-硼酸(15mmol)、碳酸钾(20mmol)、二氧六环(150mL)、四(三苯基膦)钯(0.15mmol)、水30mL加入到反应瓶中,加热至回流反应3h,TLC监控反应完成,将反应液倒入水中过滤,二氯萃取后浓缩后甲苯重结晶得中间体C。
将C(10mmol)、二苯胺(12mmol)、叔丁醇钠(15mmol)、三(二亚苄基丙酮)二钯(0.1mmol)、三叔丁基膦(0.2mmol)、二甲苯150mL加入至反应瓶中,加热至120℃反应6h,TLC监控反应完全,降温后直接过滤,滤饼用二甲苯重结晶得到化合物P17。
合成例4:
化合物P20的合成
将C(10mmol)、三苯胺-4-硼酸(12mmol)、磷酸钾(15mmol)、二氧六环(150mL)、三(二亚苄基丙酮)二钯(0.1mmol)、2-双环己基膦-2',6'-二甲氧基联苯(S-phos)(0.2mmol)加入到反应瓶中,加热至回流反应3h,TLC监控反应完成,将反应液倒入水中过滤,滤饼二甲苯重结晶得到化合物P20。
合成例5:
化合物P53的合成
与合成例3的区别在于,将二苯并噻吩-4-硼酸替换成等物质的量的二苯并呋喃-4-硼酸,得到化合物P53。
合成例6:
化合物P57的合成
将S3(30mmol)、碳酸钾(50mmol)、DMF(200mL)、咔唑(30mmol)加入到反应瓶中加热至回流反应4h,TLC监控反应完成,降温后将反应液加入水中过滤,滤饼乙醇洗涤一次干燥得中间体A。
将A(20mmol)、联频哪醇硼酸酯(30mmol)、([1,1'-双(二苯基膦基)二茂铁]二氯化钯)(pd(dppf)Cl2)(0.2mmol)、醋酸钾(30mmol)、二氧六环(200mL)加入反应瓶中,回流反应3h后加入水及二氯甲烷萃取,有机相浓缩的中间体B。
将B(15mmol)、2-氯-4-苯基喹唑啉(15mmol)、碳酸钾(20mmol)、二氧六环(150mL)、四(三苯基膦)钯(0.15mmol)、水30mL加入到反应瓶中,加热至回流反应3h,TLC监控反应完成,将反应液倒入水中过滤,二氯萃取后浓缩后甲苯重结晶得中间体C。
将C(10mmol)、二苯胺(12mmol)、叔丁醇钠(15mmol)、三(二亚苄基丙酮)二钯(0.1mmol)、三叔丁基膦(0.2mmol)、二甲苯150mL加入至反应瓶中,加热至120℃反应6h,TLC监控反应完全,降温后直接过滤,滤饼用二甲苯重结晶得到化合物P57。
合成例7:
化合物P65的合成
与合成例6的区别在于,将咔唑替换成等物质的量的9H-吡啶并[2,3-B]吲哚,得到化合物P65。
本发明示例性的给出以上几种化合物的具体合成方法,对于以下实施例中没有给出具体合成方法的化合物,也通过相似的方法制备而成,只需要替换原料即可得到,此处不再赘述,或者本领域技术人员也可以采用现有技术中其他方式制备得到。
为了验证本发明实施例中所使用的式(1)化合物分子结构的确定性,我们通过元素分析(赛默飞FLASH 2000CHNS/O有机元素分析仪)及质谱信息(英国Micromass公司制造的ZAB-HS型质谱仪)对其进行了确认,结果如表1所示。
表1
实施例1
本实施例提供一种有机电致发光器件,具体制备方法如下:
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ITO阳极的玻璃基片置于真空腔内,抽真空至<1×10-5Pa,在上述阳极层膜上按先后顺序真空热蒸镀10nm的HT-4:HI-3(97/3,w/w)混合物作为空穴注入层,60nm的化合物HT-4作为空穴传输层,40nm的化合物P1:RPD-8(100:3,w/w)二元混合物作为发光层,25nm的化合物ET-46:ET-57(50/50,w/w)混合物作为电子传输层,1nm的LiF作为电子注入层,150nm的金属铝作为阴极。所有有机层和LiF的蒸镀总速率控制在0.1nm/秒,金属电极的蒸镀速率控制在1nm/秒。
实施例2-9与实施例1的区别仅在于将化合物P1替换为其他化合物,具体详见表2。
对比例1
与实施例1的区别在于,将化合物P1替换为化合物C1(详见专利KR1020150122343A)。
对比例2
与实施例8的区别在于,将化合物P85替换为化合物C2(详见专利KR1020110041727A)。
对比例3
与实施例1的区别在于,将化合物P1替换为化合物C3(通过现有技术的合成方法制备得到)。
性能测试:
(1)在同样亮度下,使用Photo Research公司的PR 750型光辐射计、ST-86LA型亮度计(北京师范大学光电仪器厂)及Keithley4200测试系统测定实施例和对比例中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3000cd/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;
(2)LT95的寿命测试如下:使用ST-86LA型亮度计(北京师范大学光电仪器厂)在10000cd/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9500cd/m2的时间,单位为小时。
性能测试结果如表2所示。
表2
表2中的结果表明,本发明的新型有机材料用于有机电致发光器件,可以有效的降低起降电压,提高电流效率,是性能良好的红光主体材料,其中,驱动电压≤3.9V,电流效率≥16.1cd/A,LT95寿命≥58h。
对比例1与实施例1相比,发光主体材料的区别仅在于不含有芳胺基团,器件性能明显下降,驱动电压为4.5V,电流效率为15.5cd/A。
对比例2与实施例8相比,发光主体材料的区别仅在于不含有喹唑啉基团,器件性能明显下降,驱动电压为4.2V,电流效率为15.9cd/A。
对比例3与实施例1相比,发光主体材料的区别仅在于仅含有一个喹唑啉基团(即不含有Ar3),器件性能下降,驱动电压为3.8V,电流效率为13.9cd/A。
上述对比结果证明,本发明提供的化合物中喹唑啉或喹喔啉、芳胺基团以及特定结构的杂芳基(Ar3)三个取代基之间相互配合,使化合物用于有机电致发光器件时,能够提高发光效率,降低驱动电压,这三种基团缺一不可。
本发明通过上述实施例来说明本发明的详细方法,但本发明并不局限于上述详细方法,即不意味着本发明必须依赖上述详细方法才能实施。所属技术领域的技术人员应该明了,对本发明的任何改进,对本发明产品各原料的等效替换及辅助成分的添加、具体方式的选择等,均落在本发明的保护范围和公开范围之内。
Claims (13)
1.一种用于发光层主体材料的化合物,其特征在于,所述化合物具有式(1)所示的结构;
式(1)中,所述X1和X2中一个为N,另一个为CR5;
所述R1、R2、R3、R4和R5各自独立的选自氢原子、C1~C10烷基、C3~C12环烷基、C1~C12烷氧基、卤素、氰基、C6~C20芳基、C3~C20杂芳基中的任意一种,所述R1、R2、R3、R4和R5中相邻的两个取代基之间不稠合成环;
式(1)中,所述L1、L2和L3各自独立的选自单键、C6~C30亚芳基、C3~C30亚杂芳基中的任意一种;
式(1)中,所述Ar1和Ar2各自独立的选自取代或未取代的C6~C20芳基、取代或未取代的C3~C20杂芳基中的任意一种;
式(1)中,所述的Ar3选自如下基团中的任意一种:
所述s为1~7的整数,所述d为1~s的整数;
所述Rd各自独立地选自氢原子、卤素、氰基、C1~C12的烷基、C1~C12的烷氧基、C6~C20的芳基中的任意一种;
其中,虚线代表基团的连接位点;
当上述基团存在取代基时,所述取代基各自独立地选自氰基、卤素、C1~C10的烷基或环烷基、C1~C6的烷氧基或硫代烷氧基、C6~C30的单环芳基或稠环芳基。
2.根据权利要求1所述的化合物,其特征在于,所述X1为CR5,X2为N。
3.根据权利要求1所述的化合物,其特征在于,所述Rd各自独立地选自氢原子、苯基、氰基或甲氧基中的任意一种。
4.根据权利要求1所述的化合物,其特征在于,所述的Ar3选自如下基团中的任意一种:
其中,虚线代表基团的连接位点。
5.根据权利要求1所述的化合物,其特征在于,所述Ar3选自如下基团中的任意一种:
其中,虚线代表基团的连接位点。
6.根据权利要求1~5中任一项所述的化合物,其特征在于,所述Ar1和Ar2各自独立的选自苯基、萘基、二苯并噻吩基、联苯基或芴基中的任意一种。
7.根据权利要求1所述的化合物,其特征在于,所述L1、L2和L3各自独立的选自单键或C6~C30亚芳基。
8.根据权利要求1所述的化合物,其特征在于,所述L1、L2和L3各自独立的选自单键或亚苯基。
9.根据权利要求1所述的化合物,其特征在于,所述化合物具有如下所示的结构中的任意一种:
10.一种根据权利要求1~9中任一项所述的化合物的应用,其特征在于,所述化合物应用于有机电致发光器件。
11.根据权利要求10所述的化合物的应用,其特征在于,所述化合物用作所述有机电致发光器件中的发光层材料。
12.根据权利要求11所述的化合物的应用,其特征在于,所述化合物用作发光层主体材料。
13.一种有机电致发光器件,其特征在于,所述有机电致发光器件包括第一电极、第二电极以及位于第一电极和第二电极之间的有机层,所述有机层中含有权利要求1~9中任一项所述的化合物。
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN106661001A (zh) * | 2014-05-14 | 2017-05-10 | 哈佛学院院长等 | 有机发光二极管材料 |
CN108690083A (zh) * | 2017-04-06 | 2018-10-23 | 北京鼎材科技有限公司 | 化合物及其有机电致发光器件 |
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