CN111039969B - 一种有机化合物、显示面板及显示装置 - Google Patents
一种有机化合物、显示面板及显示装置 Download PDFInfo
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- CN111039969B CN111039969B CN201911399670.4A CN201911399670A CN111039969B CN 111039969 B CN111039969 B CN 111039969B CN 201911399670 A CN201911399670 A CN 201911399670A CN 111039969 B CN111039969 B CN 111039969B
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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Abstract
Description
技术领域
本申请涉及有机电致发光材料技术领域,尤其涉及一种有机化合物、显示面板及显示装置。
背景技术
根据发光机制,可用于OLED发光层材料主要有以下4种:
1、荧光材料
材料的单线激发态S1,通过辐射跃迁回到基态S0。
2、磷光材料
三线激发态T1直接辐射衰减到基态S0(Nature,1998,395,151)。
3、三线态-三线态湮灭(TTA)材料
两个三线态激子相互作用产生一个单线态激子,通过辐射跃迁回到基态S0(Adv.Funct.Mater.,2013,23,739)。
4、热活化延迟荧光(Thermally Active Delayed Fluorescence,TADF)材料
当S1态与T1态之间的能隙值较小且T1态激子寿命较长时,在一定温度条件下,T1态激子可以逆向系间窜越(RISC)实现T1→S1的过程,再由S1态辐射衰减至基态S0(Nature,2012,492,234-238)。
以上几种材料的理论最大内量子产率、结构设计多样化及材料成本如表1所示:
表1
荧光材料:根据自旋统计,激子中单线态和三线态激子的比例是1:3,所以荧光材料最大内量子产率不超过25%。依据朗伯发光模式,光取出效率为20%左右,故基于荧光材料的OLED器件的EQE不超过5%。
磷光材料:磷光材料由于重原子效应,可以通过自旋偶合作用,加强分子内部系间窜越,可以直接利用75%的三线态激子,从而实现在室温下S1和T1共同参与的发射,理论最大内量子产率可达100%。依据朗伯发光模式,光取出效率为20%左右,故基于磷光材料的OLED器件的EQE可以达到20%。但是磷光材料基本为Ir、Pt、Os、Re、Ru等重金属配合物,生产成本较高,不利于大规模生产。在高电流密度下,磷光材料存在严重的效率滚降现象,同事磷光器件的稳定性并不好。
三线态-三线态湮灭(TTA)材料:两个相邻的三线态激子,复合生成一个更高能级的单线激发态分子和一个基态分子,但是两个三线态激子产生一个单线态激子,所以理论最大内量子产率只能达到62.5%。为了防止产生较大的效率滚降现象,在这个过程中三线态激子的浓度需要调控。
热激活延迟荧光(TADF)材料:当单线激发态和三线激发态的能级差较小时,分子内部发生反向系间窜越RISC,T1态激子通过吸收环境热上转换到S1态,可同时利用75%的三线态激子和25%的单线态激子,理论最大内量子产率可达100%。主要为有机化合物,不需要稀有金属元素,生产成本低。可通过多种方法进行化学修饰。但目前已发现的TADF材料较少,新型的可用于OLED器件的TADF材料亟待开发。
发明内容
有鉴于此,本发明的目的是提供一种有机化合物,具有以下结构通式:
R1、R2、R3、R4分别独立地选自氢、取代或未取代的C4~C40芳基、取代或者非取代的C4~C40杂芳基、取代或未取代的C4~C40稠芳基、取代或未取代的C4~C40稠杂芳基;
m为R1的个数,取值为1~3;
n为R2的个数,取值为1~2;
o为R4的个数,取值为1~2;
p为R3的个数,取值为1~3。
本发明的有机化合物是一种具有热活化延迟荧光(TADF)性质的材料,作为有机电致发光器件的发光层但不限于发光层的主体或客体材料,由于该材料可利用三线态能量,可大幅度提高器件性能。
本发明的有机化合通过接入具有大位阻的基团,避免了化合物的聚集,避免共轭平面的直接堆积形成π聚集或激基缔合物,从而提高了发光效率。
本发明的有机化合物具有TADF特性,可以利用传统荧光分子跃迁禁阻得三线态激子来发光,从而提高器件效率。其根本原因在于所设计分子具有大的刚性扭曲,降低了HOMO和LUMO之间的重叠,使得三重态和单重态之间的能级差可以降低到0.25eV以下,满足三线态能量向单线态逆向窜越从而提高发光效率。
本发明的有机化合物本身具有Bipolar特性,作为发光层必将大大提高两种载流子的传输能力和改善载流子平衡,提高荧光量子效率和降低器件电压。
本发明的有机化合物制备的OLED无任何重金属(Ir,Pt,Au),成本低且更环保;与传统无重金属的荧光材料不同,本发明的有机化合物具有TADF特性,可以利用三线态激子能量,从而拥有更高的效率。
附图说明
图1是本发明实施例提供的一种利用gaussian软件计算手段模拟化合物M1的HOMO能级示意图。
图2是本发明实施例提供的一种利用gaussian软件计算手段模拟化合物M1的LUMO能级示意图。
图3是本发明实施例提供的一种利用gaussian软件计算手段模拟化合物M2的HOMO能级示意图。
图4是本发明实施例提供的一种利用gaussian软件计算手段模拟化合物M2的LUMO能级示意图。
图5是本发明实施例提供的一种利用gaussian软件计算手段模拟化合物M3的HOMO能级示意图。
图6是本发明实施例提供的一种利用gaussian软件计算手段模拟化合物M3的LUMO能级示意图。
图7是本发明实施例提供的一种利用gaussian软件计算手段模拟化合物M4的HOMO能级示意图。
图8是本发明实施例提供的一种利用gaussian软件计算手段模拟化合物M4的LUMO能级示意图。
图9是本发明实施例提供的有机发光器件的结构示意图。
具体实施方式
为了更好的理解本申请的技术方案,下面对本申请实施例进行详细描述。
应当明确,所描述的实施例仅仅是本申请一部分实施例,而不是全部的实施例。基于本申请中的实施例,本领域普通技术人员在没有作出创造性劳动前提下所获得的所有其它实施例,都属于本申请保护的范围。
在本申请实施例中使用的术语是仅仅出于描述特定实施例的目的,而非旨在限制本申请。在本申请实施例和所附权利要求书中所使用的单数形式的“一种”、“所述”和“该”也旨在包括多数形式,除非上下文清楚地表示其他含义。
应当理解,本文中使用的术语“和/或”仅仅是一种描述关联对象的关联关系,表示可以存在三种关系,例如,A和/或B,可以表示:单独存在A,同时存在A和B,单独存在B这三种情况。另外,本文中字符“/”,一般表示前后关联对象是一种“或”的关系。
本说明书的描述中,需要理解的是,本申请权利要求及实施例所描述的“基本上”、“近似”、“大约”、“约”、“大致”、“大体上”等词语,是指在合理的工艺操作范围内或者公差范围内,可以大体上认同的,而不是一个精确值。
本发明的一方面提供一种有机化合物,具有以下结构通式:
R1、R2、R3、R4分别独立地选自氢、取代或未取代的C4~C40芳基、取代或者非取代的C4~C40杂芳基、取代或未取代的C4~C40稠芳基、取代或未取代的C4~C40稠杂芳基;
m为R1的个数,取值为1~3;
n为R2的个数,取值为1~2;
o为R4的个数,取值为1~2;
p为R3的个数,取值为1~3。
根据本发明所述化合物的一个实施方式,R1、R2、R3、R4相同。
根据本发明所述化合物的一个实施方式,R1、R3相同。
根据本发明所述化合物的一个实施方式,R2、R4相同。
根据本发明所述化合物的一个实施方式,R1、R2、R3相同,或者R1、R2、R4相同,或者R2、R3、R4相同。
根据本发明所述化合物的一个实施方式,R1、R2、R3、R4分别独立地选自氢、取代或未取代苯基、取代或未取代呋喃基、取代或未取代噻吩基、取代或未取代吡啶基、取代或未取代萘基、取代或未取代的蒽基、取代或未取代氮苯基咔唑基、取代或未取代的三苯胺基、取代或未取代螺二芴基、取代或未取代二甲基芴基、取代或未取代的二苯基咔唑基、取代或未取代三苯胺基、取代或未取代氮杂蒽基、取代或未取代二联苯基、取代或未取代三联苯基、取代或未取代的四联苯基、取代或未取代的噻吩联苯胺基、取代或未取代的呋喃联苯胺基、取代或未取代的苯氧嗪基、取代或未取代的吩噁嗪基、取代或未取代的吩嗪基、取代或未取代的吩噻嗪基、取代或未取代的菲基、取代或未取代的苊烯基、取代或未取代的芘基、取代或未取代的基、取代或未取代的苯并菲基、取代或未取代的苯并蒽基、取代或未取代的荧蒽基、取代或未取代的苉基、取代或未取代的苯并呋喃基、取代或未取代的二苯并呋喃基、取代或未取代的苯并噻吩基、取代或未取代的二苯并噻吩基、取代或未取代的噻蒽基、吖啶基及其衍生物基团中的至少一种,
R1、R2、R3、R4不同时为氢。
根据本发明所述化合物的一个实施方式,R1、R2、R3、R4分别独立地选自氢或以下基团中的至少一种,
其中,#表示连接位置;
R5选自氢、卤素、羟基、硝基、C1-C20烷基、C1-C20烷氧基、取代或未取代氨基、C4-C8环烷基、C4-C40芳基、C4-C40杂芳基中的一种。
根据本发明所述化合物的一个实施方式,R1、R2、R3、R4分别独立地选自氢或以下基团中的至少一种,
其中,#表示连接位置。
根据本发明所述化合物的一个实施方式,所述有机化合物选自以下化合物中的一种:
本发明还提供一种显示面板,包括有机发光器件,该有机发光器件包括相对设置的阳极、阴极,以及位于阳极和阴极之间的发光层,所述发光层包括主体材料和客体材料,所述发光层的主体材料或客体材料为上述有机化合物中的至少一种。
本发明还提供一种显示面板,包括有机发光器件,其中该有机发光器件包括相对设置的阳极、阴极,以及位于所述阳极背离所述阴极一侧的基底层,以及位于所述阳极与所述阴极之间的有机膜层,所述有机膜层包括电子传输层、空穴传输层和发光层,所述电子传输层、空穴传输层、发光层中的至少一者的材料为上述有机化合物中的至少一种。
根据本发明所述显示面板的一个实施方式,本发明还提供一种显示装置,包括上述任一的显示面板。
在本发明所述的显示面板中,有机发光器件的阳极材料可以选自金属例如,铜、金、银、铁、铬、镍、锰、钯、铂等及它们的合金;金属氧化物例如,氧化铟、氧化锌、氧化铟锡(ITO)、氧化铟锌(IZO)等;导电性聚合物例如,聚苯胺、聚吡咯、聚(3-甲基噻吩)等。除了以上有助于空穴注入材料及其组合之外,阳极材料还可包括其他已知的适合做阳极的材料。
在本发明所述的显示面板中,有机发光器件的阴极材料可以选自金属例如,铝、镁、银、铟、锡、钛等及它们的合金;多层金属材料例如,LiF/Al、LiO2/Al、BaF2/Al等。除以上有助于电子注入的材料及其组合之外,阴极材料还可包括其他已知的适合做阴极的材料。
在本发明的一个实施例中,所述的显示面板中的有机发光器件可以这样制作:在透明或不透明的光滑的基板上形成阳极,在阳极上形成有机薄层,在有机薄层上形成阴极。有机薄层的形成可以采用如蒸镀、溅射、旋涂、浸渍、离子镀等已知的成膜方法。
上述设计的新化合物可用于有机薄层中的电子传输层、空穴传输层、发光层中的至少一者的材料,可作为主体材料或掺杂材料。
下面提供几个示例性的化合物的合成示例。
实施例1
在250ml三口瓶中依次加入化合物A(11.68g,20mmol)、THF 100ml和镁条1.2g,氮气置换,加热搅拌30min。用60ml甲苯溶解化合物二甲基氯化锡(4.38g,20mmol),将溶液缓慢滴加至反应体系中,滴加完成后自然升至室温反应6h,待反应结束后加入冰水60ml淬灭反应,分别用DCM(100ml*3)和饱和食盐水(100ml*2)萃取反应液,有机相旋蒸得到油状物,使用TOL/EtOH重结晶得到固体B。
结构确认数据如下:MALDI-TOF:573.01;
1H NMR(400MHz,Chloroform)δ7.55(s,2H),7.37(s,2H),7.33(s,2H),7.23(d,J=10.0Hz,4H),7.15(s,2H),7.08(s,2H),7.00(s,2H),6.51(s,2H),1.64(s,6H).
13C NMR(100MHz,Chloroform)δ146.93(d,J=1.3Hz),143.49(s),142.10(s),140.04(s),137.14(s),133.55(s),131.15(s),129.53–129.16(m),125.09(s),124.67(s),123.20(s),122.99(s),116.79(s),53.36(s),26.76(s).
在250ml三口烧瓶中,依次加入化合物B(11.46g,20mmol)、三溴化硼(6.26g,25mmol)和甲苯100ml,开动搅拌,氮气置换,加热至100℃回流反应24h,HPLC监测反应终点。通入Cl2,继续反应5h。降至室温,干燥过柱,有机相减压蒸馏得到化合物C。
结构确认数据如下:MALDI-TOF:514.99。
1H NMR(400MHz,Chloroform)δ7.54(s,2H),7.36(s,2H),7.32(s,2H),7.22(d,J=10.0Hz,6H),7.07(s,4H),6.99(s,2H).
13C NMR(100MHz,Chloroform)δ184.94(s),150.04(s),146.93(s),146.23(s),143.49(s),142.28(s),133.55(s),132.18(s),129.33(d,J=15.6Hz),128.77(s),127.82(s),124.67(s),123.20(s),122.99(s).
在250ml三口瓶中依次加入化合物D(6.82g,20mmol)、THF 100ml和镁条1.2g,氮气置换,加热搅拌30min。用60ml甲苯溶解化合物二甲基氯化锡(4.38g,20mmol),将溶液缓慢滴加至反应体系中,滴加完成后自然升至室温反应6h,待反应结束后加入冰水60ml淬灭反应,分别用DCM(100ml*3)和饱和食盐水(100ml*2)萃取反应液,有机相旋蒸得到油状物,使用TOL/EtOH重结晶得到固体E。
结构确认数据如下:MALDI-TOF:329.91。
1H NMR(400MHz,Chloroform)δ7.43(s,1H),7.27(s,1H),7.20(s,1H),7.05(s,1H),6.47(s,1H),1.64(s,6H).
13C NMR(100MHz,Chloroform)δ149.00(s),143.09(s),137.23(s),131.14(s),128.95(d,J=10.4Hz),126.45(s),114.92(s),53.36(s),26.76(s).
在250ml三口烧瓶中,依次加入化合物E(6.60g,20mmol)、三溴化硼(6.26g,25mmol)和甲苯100ml,开动搅拌,氮气置换,加热至100℃回流反应24h,HPLC监测反应终点。通入Cl2,继续反应5h。降至室温,干燥过柱,有机相减压蒸馏得到化合物F。
结构确认数据如下:MALDI-TOF:271.88。
1H NMR(400MHz,Chloroform)δ7.53(s,1H),7.27(s,2H),7.20(s,2H).
13C NMR(100MHz,Chloroform)δ184.94(s),148.15(s),144.60(s),130.16(s),128.80(s),127.74(s),127.19(s).
将化合物C(10.30g,20mmol)加入反应瓶中,加入***(50mL)溶解,氮气置换三次。降温至-78℃,待温度达到后控制温度在-65℃以下缓慢滴加n-BuLi 16.08mL(2.5M,40mmol),滴加完全后搅拌30min。再用60mL甲苯溶解化合物F(5.43g,20mmol),缓慢滴加至反应液中,滴加完成后自然升至室温反应6h。反应结束后加入冰水(100mL)淬灭反应。再加入DCM(80mL*2)萃取,最后用饱和食盐水萃取一次。收集有机相旋蒸,得到淡黄色油状物。柱层析(流动相正己烷:二氯甲烷=3:1)纯化产物,得到化合物M1。
结构确认数据如下:MALDI-TOF:467.20。
1H NMR(400MHz,Chloroform)δ7.63(s,1H),7.55(s,4H),7.37(s,4H),7.27(d,J=5.0Hz,6H),7.25(d,J=10.0Hz,4H),7.08(s,4H),7.00(s,2H).
13C NMR(100MHz,Chloroform)δ174.20(s),162.64(s),159.21(s),146.93(s),144.30(s),143.67(s),143.49(s),139.06(s),138.67(d,J=19.5Hz),133.55(s),129.75(s),129.33(d,J=15.6Hz),126.79(s),126.15(s),124.67(s),123.66(s),123.20(s),122.99(s),121.17(s).
图1是本发明实施例提供的一种利用gaussian软件计算手段模拟化合物M1的HOMO能级示意图。图2是本发明实施例提供的一种利用gaussian软件计算手段模拟化合物M1的LUMO能级示意图。由图1和2中可以明显看出,分子的HOMO和LUMO分别排布在不同的Unit上,实现了比较完全的分离separation,这有助于减小隙间能差△EST,从而提高逆隙间窜越能力。
实施例2
在250ml三口瓶中依次加入化合物2-1(11.68g,20mmol)、THF 100ml和镁条1.2g,氮气置换,加热搅拌30min。用60ml甲苯溶解化合物二甲基氯化锡(4.38g,20mmol),将溶液缓慢滴加至反应体系中,滴加完成后自然升至室温反应6h,待反应结束后加入冰水60ml淬灭反应,分别用DCM(100ml*3)和饱和食盐水(100ml*2)萃取反应液,有机相旋蒸得到油状物,使用TOL/EtOH重结晶得到固体3-1。
结构确认数据如下:MALDI-TOF:573.01;
1H NMR(400MHz,Chloroform)δ7.55(s,2H),7.37(s,2H),7.33(s,2H),7.23(d,J=10.0Hz,4H),7.15(s,2H),7.08(s,2H),7.00(s,2H),6.51(s,2H),1.64(s,6H).
13C NMR(100MHz,Chloroform)δ146.93(d,J=1.3Hz),143.49(s),142.10(s),140.04(s),137.14(s),133.55(s),131.15(s),129.53–129.16(m),125.09(s),124.67(s),123.20(s),122.99(s),116.79(s),53.36(s),26.76(s).
在250ml三口烧瓶中,依次加入化合物3-1(11.46g,20mmol)、三溴化硼(6.26g,25mmol)和甲苯100ml,开动搅拌,氮气置换,加热至100℃回流反应24h,HPLC监测反应终点。通入Cl2,继续反应5h。降至室温,干燥过柱,有机相减压蒸馏得到化合物4-1。
结构确认数据如下:MALDI-TOF:514.99。
1H NMR(400MHz,Chloroform)δ7.54(s,2H),7.36(s,2H),7.32(s,2H),7.22(d,J=10.0Hz,6H),7.07(s,4H),6.99(s,2H).
13C NMR(100MHz,Chloroform)δ184.94(s),150.04(s),146.93(s),146.23(s),143.49(s),142.28(s),133.55(s),132.18(s),129.33(d,J=15.6Hz),128.77(s),127.82(s),124.67(s),123.20(s),122.99(s).
将化合物4-1(10.30g,20mmol)加入反应瓶中,加入***(50mL)溶解,氮气置换三次。降温至-78℃,待温度达到后控制温度在-65℃以下缓慢滴加n-BuLi 16.08mL(2.5M,40mmol),滴加完全后搅拌30min。再用60mL甲苯溶解化合物4-1(10.30g,20mmol),缓慢滴加至反应液中,滴加完成后自然升至室温反应6h。反应结束后加入冰水(100mL)淬灭反应。再加入DCM(80mL*2)萃取,最后用饱和食盐水萃取一次。收集有机相旋蒸,得到淡黄色油状物。柱层析(流动相正己烷:二氯甲烷=3:1)纯化产物,得到化合物M2。
结构确认数据如下:MALDI-TOF:710.31。
1H NMR(400MHz,Chloroform)δ7.55(s,4H),7.37(s,4H),7.26(d,J=16.0Hz,10H),7.08(s,10H),7.00(s,8H)
13C NMR(100MHz,Chloroform)δ174.20(s),162.64(s),146.93(s),144.30(s),143.49(s),138.67(d,J=15.6Hz),133.55(s),129.33(d,J=12.5Hz),126.15(s),124.67(s),123.20(s),122.99(s),121.17(s).
图3是本发明实施例提供的一种利用gaussian软件计算手段模拟化合物M2的HOMO能级示意图。图4是本发明实施例提供的一种利用gaussian软件计算手段模拟化合物M2的LUMO能级示意图。由图3和4中可以明显看出,分子的HOMO和LUMO分别排布在不同的Unit上,实现了比较完全的分离separation,这有助于减小隙间能差△EST,从而提高逆隙间窜越能力。
实施例3
在250ml三口瓶中依次加入化合物M3-1(11.68g,20mmol)、THF 100ml和镁条1.2g,氮气置换,加热搅拌30min。用60ml甲苯溶解化合物二甲基氯化锡(4.38g,20mmol),将溶液缓慢滴加至反应体系中,滴加完成后自然升至室温反应6h,待反应结束后加入冰水60ml淬灭反应,分别用DCM(100ml*3)和饱和食盐水(100ml*2)萃取反应液,有机相旋蒸得到油状物,使用TOL/EtOH重结晶得到固体M3-2。
结构确认数据如下:MALDI-TOF:573.01;
1H NMR(400MHz,Chloroform)δ7.55(s,2H),7.37(s,2H),7.33(s,2H),7.23(d,J=10.0Hz,4H),7.15(s,2H),7.08(s,2H),7.00(s,2H),6.51(s,2H),1.64(s,6H).
13C NMR(100MHz,Chloroform)δ146.93(d,J=1.3Hz),143.49(s),142.10(s),140.04(s),137.14(s),133.55(s),131.15(s),129.53–129.16(m),125.09(s),124.67(s),123.20(s),122.99(s),116.79(s),53.36(s),26.76(s).
在250ml三口烧瓶中,依次加入化合物M3-2(11.46g,20mmol)、三溴化硼(6.26g,25mmol)和甲苯100ml,开动搅拌,氮气置换,加热至100℃回流反应24h,HPLC监测反应终点。通入Cl2,继续反应5h。降至室温,干燥过柱,有机相减压蒸馏得到化合物M3-3。
结构确认数据如下:MALDI-TOF:514.99。
1H NMR(400MHz,Chloroform)δ7.54(s,2H),7.36(s,2H),7.32(s,2H),7.22(d,J=10.0Hz,6H),7.07(s,4H),6.99(s,2H).
13C NMR(100MHz,Chloroform)δ184.94(s),150.04(s),146.93(s),146.23(s),143.49(s),142.28(s),133.55(s),132.18(s),129.33(d,J=15.6Hz),128.77(s),127.82(s),124.67(s),123.20(s),122.99(s).
将化合物M3-3(10.30g,20mmol)加入反应瓶中,加入***(50mL)溶解,氮气置换三次。降温至-78℃,待温度达到后控制温度在-65℃以下缓慢滴加n-BuLi 16.08mL(2.5M,40mmol),滴加完全后搅拌30min。再用60mL甲苯溶解化合物M3-4(10.26g,20mmol),缓慢滴加至反应液中,滴加完成后自然升至室温反应6h。反应结束后加入冰水(100mL)淬灭反应。再加入DCM(80mL*2)萃取,最后用饱和食盐水萃取一次。收集有机相旋蒸,得到淡黄色油状物。柱层析(流动相正己烷:二氯甲烷=3:1)纯化产物,得到化合物M3。
结构确认数据如下:MALDI-TOF:708.29。
1H NMR(400MHz,Chloroform)δ8.55(s,1H),8.19(s,1H),7.82(s,2H),7.73(d,J=4.0Hz,4H),7.63–7.38(m,6H),7.38–7.31(m,6H),7.31–7.06(m,10H),7.00(s,4H).
13C NMR(100MHz,Chloroform)δ170.42(s),158.10(s),151.17(s),149.92(s),146.93(s),144.41(s),142.90(s),139.31(s),137.94(s),137.69(s),135.38(s),133.42(s),132.46(s),130.97(s),130.74(s),130.20(s),129.67(s),129.27(s),127.76(d,J=7.2Hz),126.89(s),126.15(s),125.67(s),124.67(s),123.39(s),122.99(s),121.31–121.03(m),117.07(s),114.89(d,J=13.7Hz).
图5是本发明实施例提供的一种利用gaussian软件计算手段模拟化合物M3的HOMO能级示意图。图6是本发明实施例提供的一种利用gaussian软件计算手段模拟化合物M3的LUMO能级示意图。由图5和6中可以明显看出,分子的HOMO和LUMO分别排布在不同的Unit上,实现了比较完全的分离separation,这有助于减小隙间能差△EST,从而提高逆隙间窜越能力。
实施例4
在250ml三口瓶中依次加入化合物M4-1(16.31g,20mmol)、THF 100ml和镁条1.2g,氮气置换,加热搅拌30min。用60ml甲苯溶解化合物二甲基氯化锡(4.38g,20mmol),将溶液缓慢滴加至反应体系中,滴加完成后自然升至室温反应6h,待反应结束后加入冰水60ml淬灭反应,分别用DCM(100ml*3)和饱和食盐水(100ml*2)萃取反应液,有机相旋蒸得到油状物,使用TOL/EtOH重结晶得到固体M4-2。
结构确认数据如下:MALDI-TOF:806.01;
1H NMR(400MHz,Chloroform)δ7.37(d,J=1.6Hz,2H),7.34(s,4H),7.50–7.24(m,8H),7.24–7.03(m,18H),7.00(s,3H).
13C NMR(100MHz,Chloroform)δ153.78(s),149.00(s),147.04–146.73(m),142.49(s),140.34(s),139.59(s),136.88(s),135.33(s),134.49(t,J=12.7Hz),131.20(s),130.20(s),129.32(d,J=11.3Hz),125.07(s),124.67(s),118.47(s),109.41(s),97.62(s),-6.21(s).
在250ml三口烧瓶中,依次加入化合物M4-2(16.13g,20mmol)、三溴化硼(6.26g,25mmol)和甲苯100ml,开动搅拌,氮气置换,加热至100℃回流反应24h,HPLC监测反应终点。通入Cl2,继续反应5h。降至室温,干燥过柱,有机相减压蒸馏得到化合物M4-3。
结构确认数据如下:MALDI-TOF:748.07。
1H NMR(400MHz,Chloroform)δ7.37(d,J=1.6Hz,2H),7.34(s,4H),7.50–7.24(m,8H),7.24–7.03(m,12H),7.00(s,3H).
13C NMR(100MHz,Chloroform)δ159.07(s),153.78(s),151.90(s),147.04–146.73(m),142.63(s),140.34(s),138.91(s),135.48(s),133.84(s),132.45(s),131.65(s),130.83(s),130.20(s),129.32(d,J=11.3Hz),126.98(s),125.07(s),124.67(s),119.46(s),109.41(s),97.62(s).
将化合物M4-3(14.92g,20mmol)加入反应瓶中,加入***(50mL)溶解,氮气置换三次。降温至-78℃,待温度达到后控制温度在-65℃以下缓慢滴加n-BuLi 16.08mL(2.5M,40mmol),滴加完全后搅拌30min。再用60mL甲苯溶解化合物M4-4(12.66g,20mmol),缓慢滴加至反应液中,滴加完成后自然升至室温反应6h。反应结束后加入冰水(100mL)淬灭反应。再加入DCM(80mL*2)萃取,最后用饱和食盐水萃取一次。收集有机相旋蒸,得到淡黄色油状物。柱层析(流动相正己烷:二氯甲烷=3:1)纯化产物,得到化合物M4。
结构确认数据如下:MALDI-TOF:1059.42。
1H NMR(400MHz,Chloroform)δ8.55(s,1H),8.19(s,1H),7.82(s,2H),7.73(d,J=4.0Hz,5H),7.54(d,J=12.0Hz,5H),7.39(d,J=12.0Hz,4H),7.31–6.80(m,27H),2.31(s,6H).
13C NMR(100MHz,Chloroform)δ223.99(s),165.99(s),158.10(s),153.78(s),147.14–146.69(m),143.57(s),140.95(s),140.34(s),139.31(s),139.06(s),137.69(s),137.40(d,J=10.5Hz),135.48(d,J=19.9Hz),135.02(s),134.27(s),132.99(s),132.27(s),131.05(s),130.50(s),130.20(d,J=0.8Hz),129.38(s),129.08(s),127.72(s),127.16(s),125.93–125.54(m),123.59(d,J=16.4Hz),122.41(s),121.15(d,J=2.7Hz),120.90(s),120.58(s),119.00(s),116.41(s),114.89(d,J=13.7Hz),109.41(s),108.52(s),97.62(s),21.83(s).
图7是本发明实施例提供的一种利用gaussian软件计算手段模拟化合物M4的HOMO能级示意图。图8是本发明实施例提供的一种利用gaussian软件计算手段模拟化合物M4的LUMO能级示意图。由图7和8中可以明显看出,分子的HOMO和LUMO分别排布在不同的Unit上,实现了比较完全的分离separation,这有助于减小隙间能差△EST,从而提高逆隙间窜越能力。
由图1~8中可以明显看出,分子的HOMO和LUMO分别排布在不同的Unit上,实现了比较完全的separation,这有助于减小隙间能差△EST,从而提高逆隙间窜越能力。
表1化合物的能级图
由上表1可以看出,本发明提供的有机化合物具有TADF特性,可以利用传统荧光分子跃迁禁阻的三线态激子来发光,从而提高器件效率,本发明提供的化合物具有大的刚性扭曲,降低了HOMO和LUMO之间的重叠,使得三重态和单重态之间的能级差可以降低到0.25eV以下,满足三线态能量向单线态逆向窜越从而提高发光效率。
有机化合物应用于有机发光器件中:
本实施例提供一种有机发光器件,其结构如图9所示,所述有机发光器件包括:基板1、阳极2(ITO)、空穴注入层3、第一空穴传输层4、第二空穴传输层5、发光层6、第一电子传输层7、第二电子传输层8、电子注入层9和阴极10(铝电极),图9中向上的箭头代表出光方向,其中ITO阳极2的厚度是10nm,空穴注入层3的厚度是5nm,第一空穴传输层4的厚度是50nm、第二空穴传输层5的厚度是10nm、发光层6的厚度是30nm、第一电子传输层7的厚度是5nm、第二电子传输层8的厚度是20nm、电子注入层9的厚度是1nm,铝电极10的厚度是15nm。
以下提供几个本发明的有机化合物应用于有机发光器件中的应用实施例。
应用实施例1
有机发光器件01的制备过程如下::
1)将玻璃基板1切成50mm×50mm×0.7mm的大小,分别在异丙醇和去离子水中超声处理30分钟,然后暴露在臭氧下约10分钟来进行清洁;将所得的具有ITO阳极2的玻璃基板安装到真空沉积设备上;
2)在真空度为2×10-6Pa下,在ITO阳极层2上,通过真空蒸镀方式蒸镀空穴注入层材料HAT-CN,厚度为5nm,该层作为空穴注入层3;
3)在空穴注入层3上真空蒸镀第一空穴传输层4材料为N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(α-NPD),厚度为50nm,作为第一空穴传输层4;
4)在第一空穴传输层4上真空蒸镀第二空穴传输层5材料为1,3-二咔唑-9-基苯(mCP),厚度为10nm,作为第二空穴传输层5;
5)第二空穴传输层5上共沉积发光层6,其中,用化合物M1作为发光层的主体材料,Ir(ppy)3作为掺杂材料,掺杂比例为8%(质量比),厚度为30nm;
6)在发光层6上真空蒸镀第一电子传输层7,第一电子传输层7的材料为二苯基[4-(三苯基硅烷基)苯基]氧膦(TSPO1),厚度为5nm;
7)在第一电子传输层7上真空蒸镀第二电子传输层8,第二电子传输层8的材料为TPBi,厚度为20nm;
8)在第二电子传输层8真空蒸镀电子注入层9,电子注入层9的材料为LiF,厚度为1nm;
9)在电子注入层9上真空蒸镀铝电极,厚度为15nm,作为阴极10。
应用实施例2
有机发光器件02的制备方法同应用实施例1,与应用实施例1的区别在于,将化合物M1替换为化合物M2。
应用实施例3
有机发光器件03的制备方法同应用实施例1,与应用实施例1的区别在于,将化合物M1替换为化合物M3。
应用实施例4
有机发光器件04的制备方法同应用实施例1,与应用实施例1的区别在于,将化合物M1替换为化合物M4。
应用比较例1
有机发光器件05的制备方法同应用实施例1,与应用实施例1的区别在于,将化合物M1替换为DCJTB。
表2
由上表2可以看出,本申请的有机化合物制备的有机发光器件的外量子效率较高,制备的OLED器件电流效率和发光效率高。
本发明的又一方面还提供一种显示装置,其包括如上文所述的有机发光显示面板。
在本发明中,有机发光器件可以是OLED,其可以用在有机发光显示装置中,其中有机发光显示装置可以是手机显示屏、电脑显示屏、液晶电视显示屏、智能手表显示屏、智能汽车显示面板、VR或AR头盔显示屏、各种智能设备的显示屏等。
以上所述仅为本申请的较佳实施例而已,并不用以限制本申请,凡在本申请的精神和原则之内,所做的任何修改、等同替换、改进等,均应包含在本申请保护的范围之内。
Claims (8)
2.根据权利要求1所述的有机化合物,其特征在于,R1、R2、R3、R4相同。
3.根据权利要求1所述的有机化合物,其特征在于,R1、R3相同。
4.根据权利要求1所述的有机化合物,其特征在于,R2、R4相同。
5.根据权利要求1所述的有机化合物,其特征在于,R1、R2、R3相同,或者R1、R2、R4相同,或者R2、R3、R4相同。
7.一种显示面板,包括有机发光器件,所述有机发光器件包括相对设置的阳极、阴极,以及位于阳极和阴极之间的发光层,所述发光层包括主体材料和客体材料,其特征在于,所述发光层的主体材料为权利要求1至6任一项所述的有机化合物中的至少一种。
8.一种显示装置,包括权利要求7所述的显示面板。
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