CN106328816A - 一种有机电致发光器件及其制备方法 - Google Patents
一种有机电致发光器件及其制备方法 Download PDFInfo
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- CN106328816A CN106328816A CN201510334281.9A CN201510334281A CN106328816A CN 106328816 A CN106328816 A CN 106328816A CN 201510334281 A CN201510334281 A CN 201510334281A CN 106328816 A CN106328816 A CN 106328816A
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- organic electroluminescent
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- 0 *N=C(C(c1ccc[s]1)=CC=C1c(cc2)ccc2N(c2ccccc2)c2ccccc2)C1=N Chemical compound *N=C(C(c1ccc[s]1)=CC=C1c(cc2)ccc2N(c2ccccc2)c2ccccc2)C1=N 0.000 description 4
- CLJODBZETXWTHG-UHFFFAOYSA-N N#Cc(cc1)ccc1N1C(c(cc2)ccc2-c(cc2)ccc2N(c2ccccc2)c2ccccc2)N=C2c3ccccc3-c3ccccc3C12 Chemical compound N#Cc(cc1)ccc1N1C(c(cc2)ccc2-c(cc2)ccc2N(c2ccccc2)c2ccccc2)N=C2c3ccccc3-c3ccccc3C12 CLJODBZETXWTHG-UHFFFAOYSA-N 0.000 description 1
- IFXRQZSQIIOXRN-UHFFFAOYSA-N c(cc1)ccc1-c(c1n[s]nc11)ccc1-c(cc1)ccc1N(c1ccccc1)c1ccccc1 Chemical compound c(cc1)ccc1-c(c1n[s]nc11)ccc1-c(cc1)ccc1N(c1ccccc1)c1ccccc1 IFXRQZSQIIOXRN-UHFFFAOYSA-N 0.000 description 1
- VUAXJOPFMQTSPS-UHFFFAOYSA-N c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c1ccc(C(N(C23)c4ccccc4)N=C2c2ccccc2-c2c3cccc2)cc1 Chemical compound c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c1ccc(C(N(C23)c4ccccc4)N=C2c2ccccc2-c2c3cccc2)cc1 VUAXJOPFMQTSPS-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及有机电致发光器件,包括基板,以及依次形成在所述基板上的发光器件,所述发光器件是由第一电极层、发光层和第二电极层组成;所述发光层包括主体材料和染料;所述主体材料为是由具有空穴传输能力和空穴传输能力的材料构成;所述主体材料中的至少一种材料的三线态能级T1高于三线态能级S1,并且T1-S1≤0.3eV;或者,所述主体材料中的至少一种材料的三线态能级T1高于三线态能级S1,并且T1-S1≥1eV,并且第二三线态能级和第一单线态能级的差值为-0.1~0.1eV。本发明采用的器件结构可以充分利用主体材料和染料中的三线态能量,提高发光效率的同时,增强了器件的使用寿命。
Description
技术领域
本发明涉及有机电致发光器件技术领域,特别是一种有机层为单一结构的有机电致发光器件。
背景技术
有机电致发光器件OLED通常包括多个像素,每个像素由若干子像素组成。目前在中小尺寸中广泛应用方案之一是由红、绿、蓝三种像素组成一个像素。每种像素包括空穴传输层、发光层、电子传输层,发光层与电子传输层之间设置有空穴/激子阻挡层,所述的发光层包括蓝光发光层,绿光发光层或红光发光层。此外,还可能需要在空穴传输层和空穴传输层之间设置绿光补偿层和红光补偿层,进一步增加了工艺步骤路线。
为解决上述问题,人们探索采用单层发光层的器件结构,传统的单层OLED器件因为多数有机材料的载流子注入不平衡,且载流子的传输速度的巨大差异性,容易导致发光区域偏移至迁移率小的注入电极一侧,如果是金属电极,则容易导致电极对发光的淬灭,从而使效率和寿命受到影响。
发明内容
为此,本发明所要解决的技术问题在于现有结构的单层结构有机电致发光器件由于激子猝灭导致的器件寿命短的问题,进而提供一种有机电致发光器件,该电致发光器件的主体材料的三线态能级T1和单线态能级S1差T1-S1≤0.3eV,本发明采用的器件结构可以充分利用主体材料和染料中的三线态能量,提高发光效率的同时,增强了器件的使用寿命。
本发明还提供一种上述有机电致发光器件的制备方法。
为解决上述技术问题,本发明采用如下技术方案:
一种有机电致发光器件,包括基板,以及依次形成在所述基板上的发光器件,所述发光器件是由第一电极层、发光层和第二电极层组成;所述发光层包括主体材料和染料;
所述主体材料为是由具有空穴传输能力和空穴传输能力的材料构成;
所述主体材料中的至少一种材料的CT激发态的三线态能级T1高于n-π激发态的三线态能级S1,并且T1-S1≤0.3eV;或者,
所述主体材料中的至少一种材料的CT激发态的三线态能级T1高于n-π激发态的三线态能级S1,并且T1-S1≥1eV,并且所述主体材料的n-π激发态的第二三线态能级和CT激发态的第一单线态能级的差值为-0.1~0.1eV。
优选地,所述主体材料为激基复合物,所述的激基复合物为热活化延迟荧光材料。
另一优选地,所述主体材料为电子传输型材料和空穴传输型材料构成的激基复合物,二者的质量比为1:9-9:1。所述电子传输型材料和/或空穴传输型材料的T1-S1≤0.3eV;或电子传输型材料和/或空穴传输型材料的T1-S1≥1eV,并且所述主体材料的n-π激发态的第二三线态能级和CT激发态的第一单线态能级的差值为-0.1~0.1eV。
再一优选地,所述主体材料为热活化延迟荧光材料TADF和空穴传输型材料的组合物,二者的质量比为1:9-9:1。所述热活化延迟荧光材料TADF和/或空穴传输型材料的T1-S1≤0.3eV;或热活化延迟荧光材料TADF和/或空穴传输型材料的T1-S1≥1eV,并且所述主体材料的n-π激发态的第二三线态能级和CT激发态的第一单线态能级的差值为-0.1~0.1eV。
再一优选地,所述主体材料为热活化延迟荧光材料TADF和电子传输型材料的组合物,二者的质量比为1:9-9:1。所述热活化延迟荧光材料TADF和/或电子传输型材料的T1-S1≤0.3eV;或热活化延迟荧光材料TADF和/或电子传输型材料的T1-S1≥1eV,并且所述主体材料的n-π激发态的第二三线态能级和CT激发态的第一单线态能级的差值为-0.1~0.1eV。
所述的染料为荧光材料和/或磷光材料,所述荧光材料的掺杂浓度为0.5-10wt%,所述磷光材料的掺杂浓度为0.5-20wt%。
所述发光层(2)为的厚度为50-150nm。
所述电子传输型材料为三(8-羟基喹啉)铝、2,9-二甲基-4,7-二苯基-1,10-邻菲咯啉、4,7-二苯基-1,10-邻菲咯啉、二(2-甲基-8-喹啉基)-4-苯基苯酚铝(III)、1,3,5-三(1-苯基-1H-苯并咪唑-2-基)苯或1,3,5-三[(3-吡啶基)-3-苯基]苯;
空穴传输型材料为N,N’-二-1-萘基)-N,N’-二苯基-1,1’-联苯基-4,4’-二胺、N,N’-二苯基-N,N’-双(间甲基苯基)-1,1’-联苯基-4,4’-二胺、4,4'-环己基二[N,N-二(4-甲基苯基)]苯胺、4,4'-N,N'-二咔唑-联苯、4,4',4”-三(咔唑-9-基)三苯胺或1,3-二咔唑-9-基苯;
所述热活化延迟荧光材料TADF具有式(1-1)-(1-100)所示结构:
一种所述的有机电致发光器件的制备方法,包括下述步骤:
在基板上使用开口掩膜板依次蒸镀第一电极层,发光层和第二电极层;
所述发光层的主体材料和染料采用共蒸镀方式。
本发明的上述技术方案相比现有技术具有以下优点:
(1)本发明的目的在于构筑单层的器件结构,提供的有机电致发光器件只需要包括第一电极层、发光层和第二电极层,所述的发光层仅由主体材料和染料采用共蒸镀方式制备,无需制备空穴传输层、空穴阻挡层、电子传输层,电子阻挡层等相关有机层,极大的简化了器件结构,缩短了制备工艺,降低了制备成本。
(2)本发明的发光层主体材料的T1-S1≤0.3eV,该类材料为具有小单三线态能级差的材料,具体是热活化延迟荧光材料TADF,或者电子传输型材料和空穴传输型材料构成的激基复合物,或者电子传输型的热活化延迟荧光材料TADF和空穴传输型材料的组合物,或者空穴传输型的热活化延迟荧光材料TADF和电子传输型材料的组合物,这三种组合的材料具有给体和受体基团,因此具有同时传输空穴和电子的能力。同时,本发明采用的器件结构可以充分利用主体材料和染料中的三线态能量,这是因为单三线态能级差小,有利于电子和空穴的注入,解决了激子淬灭造成的效率低和寿命短的问题。因此,提高发光效率的同时,增强了器件的使用寿命。
附图说明
为了使本发明的内容更容易被清楚地理解,下面根据本发明的具体实施例并结合附图,对本发明作进一步详细的说明,其中
图1为本发明的有机电致发光器件的结构示意图;
其中:1-第一电极层,2-发光层,3-第二电极层。
具体实施方式
下面将通过具体实施例对本发明作进一步的描述。
本发明可以以许多不同的形式实施,而不应该被理解为限于在此阐述的实施例。相反,提供这些实施例,使得本公开将是彻底和完整的,并且将把本发明的构思充分传达给本领域技术人员,本发明将仅由权利要求来限定。在附图中,为了清晰起见,会夸大层和区域的尺寸和相对尺寸。应当理解的是,当元件例如层、区域或基板被称作“形成在”或“设置在”另一元件“上”时,该元件可以直接设置在所述另一元件上,或者也可以存在中间元件。相反,当元件被称作“直接形成在”或“直接设置在”另一元件上时,不存在中间元件。
如图1所示,本发明的有机电致发光器件,包括基板,以及依次形成在所述基板上的发光器件,所述发光器件是由第一电极层1、发光层2和第二电极层3组成;所述发光层是由主体材料和染料组成;
所述主体材料为是由具有空穴传输能力和空穴传输能力的材料构成;
所述主体材料中的至少一种材料的CT激发态的三线态能级T1高于n-π激发态的三线态能级S1,并且T1-S1≤0.3eV;或者,
所述主体材料中的至少一种材料的CT激发态的三线态能级T1高于n-π激发态的三线态能级S1,并且T1-S1≥1eV,并且所述主体材料的n-π激发态的第二三线态能级和CT激发态的第一单线态能级的差值为-0.1~0.1eV。
所述热活化延迟荧光材料为存在电荷转移跃迁的材料,热活化延迟荧光材料中同时存在给体基团单元和受体基团单元,同时具有电子传输能力和空穴传输能力,所述给体基团单元为一个给体基团或两个以上的给体基团连接构成的基团;所述受体基团单元为一个受体基团或两个以上的受体基团连接构成的基团;具体地,所述热活化延迟荧光材料为具有式(1-1)至式(1-100)所示结构的化合物。
本发明中的主体材料可以为单一的热活化延迟荧光材料构成的激基复合物,也可以是电子传输型材料和空穴传输型材料构成的激基复合物。或者热活化延迟荧光材料TADF和空穴传输型材料构成的组合物,主体材料为热活化延迟荧光材料TADF和电子传输型材料构成的组合物。
所述电子传输型材料为三(8-羟基喹啉)铝、2,9-二甲基-4,7-二苯基-1,10-邻菲咯啉、4,7-二苯基-1,10-邻菲咯啉、二(2-甲基-8-喹啉基)-4-苯基苯酚铝(III)、1,3,5-三(1-苯基-1H-苯并咪唑-2-基)苯或1,3,5-三[(3-吡啶基)-3-苯基]苯;
空穴传输型材料为N,N’-二-1-萘基)-N,N’-二苯基-1,1’-联苯基-4,4’-二胺、N,N’-二苯基-N,N’-双(间甲基苯基)-1,1’-联苯基-4,4’-二胺、4,4'-环己基二[N,N-二(4-甲基苯基)]苯胺、4,4'-N,N'-二咔唑-联苯、4,4',4”-三(咔唑-9-基)三苯胺或1,3-二咔唑-9-基苯;
本发明中使用的红光染料为下式所示:
本发明中使用的绿光染料为下式所示:
本发明中使用的蓝光染料为下式所示:
实施例1
本实施例的器件1结构如下:
glass/ITO/1-24:CBP:Ir(piq)2(acac)(5%)/cathode
器件1中是由基板、阳极层、发光层和阴极层组成,不需要空穴注入层、空穴传输层、电子注入层、电子传输层等,发光层主体材料为式(1-24)所示热活化敏化荧光材料和空穴传输型材料CBP构成,二者的质量比为1:1。
实施例2
本实施例的器件2结构如下:
glass/ITO/1-88:BAlq:Ir(piq)2(acac)(5%)/cathode
器件2中发光层主体材料为电子传输型材料和式(1-88)所示热活化敏化荧光材料构成,二者的质量比为1:1;此处热活化敏化荧光材料为空穴传输型材料。
实施例3
本实施例的器件3结构如下:
glass/ITO/1-88:1-24:Ir(piq)2(acac)(5%)/cathode
器件3中发光层主体材料为电子传输型热活化敏化荧光材料和空穴传输型热活化敏化荧光材料构成的激基复合物,二者的质量比为1:1。
对比例1
本对比例的对比器件1结构如下:
glass/ITO/HIL/HTL/CBP:Ir(piq)2(acac)(5%)/HBL/ETL/cathode
对比例2
本对比例的对比器件2结构如下:
glass/ITO/HIL/HTL/BAlq:Ir(piq)2(acac)(20%)/HBL/ETL/cathode
对比例3
本对比例的对比器件3结构如下:
glass/ITO/HIL/HTL/CBP:BAlq:Ir(piq)2(acac)(5%)/HBL/ETL/cathode
表1
实施例4-12:
本实施例的器件4-12结构如下:
glass/ITO/TADF:空穴传输型材料:荧光材料/cathode
其中TADF、空穴传输型材料、荧光材料采用的材料及所占比例如表2;
其中荧光材料的掺杂浓度是指荧光材料占发光层总重量的比例,即荧光材料的掺杂浓度=荧光材料的质量/(荧光材料的质量+TADF的质量+空穴传输型材料)×100%
表2
| TADF | 空穴传输型材料 | 二者质量比 | 荧光材料 | 荧光材料占比 | |
| 器件4 | 式(1-1) | NPB | 1:9 | DCJT | 15wt% |
| 器件5 | 式(1-2) | TCTA | 2:8 | BCzVBi | 15wt% |
| 器件6 | 式(1-3) | CBP | 3:7 | DPAVBi | 5wt% |
| 器件7 | 式(1-4) | mCP | 4:5 | BCzVBi | 5wt% |
| 器件8 | 式(1-5) | TPD | 5:4 | DCJT | 5wt% |
| 器件9 | 式(1-6) | TAPC | 6:3 | DCJT | 5wt% |
| 器件10 | 式(1-11) | CBP | 7:2 | BCzVBi | 5wt% |
| 器件11 | 式(1-15) | mCP | 8:1 | DPAVBi | 5wt% |
| 器件12 | 式(1-20) | mCP | 9:1 | BCzVBi | 5wt% |
实施例13-30:
本实施例的器件13-30结构如下:
glass/ITO/TADF:电子传输型材料:荧光材料/cathode
其中TADF:电子传输型材料:荧光材料采用的材料及所占比例如表3;
其中荧光材料的掺杂浓度是指荧光材料占发光层总重量的比例,即荧光材料的掺杂浓度=荧光材料的质量/(荧光材料的质量+TADF的质量+电子传输型材料)×100%
表3
| TADF | 电子传输型材料 | 二者质量比 | 荧光材料 | 荧光材料占比 | |
| 器件13 | 式(1-21) | TmPyPB | 1:9 | DCJT | 5wt% |
| 器件14 | 式(1-22) | TPBi | 2:8 | BCzVBi | 5wt% |
| 器件15 | 式(1-23) | BCP | 3:7 | DPAVBi | 5wt% |
| 器件16 | 式(1-24) | Bphen | 4:5 | BCzVBi | 5wt% |
| 器件17 | 式(1-25) | BCP | 5:4 | DCJT | 5wt% |
| 器件18 | 式(1-26) | Alq3 | 6:3 | BCzVBi | 5wt% |
| 器件19 | 式(1-31) | Bphen | 7:2 | DPAVBi | 5wt% |
| 器件20 | 式(1-35) | BCP | 8:1 | BCzVBi | 5wt% |
| 器件21 | 式(1-40) | BAlq | 9:1 | DCJT | 5wt% |
| 器件22 | 式(1-45) | Alq3 | 1:9 | DCM | 5wt% |
| 器件23 | 式(1-48) | BAlq | 2:8 | DMQA | 15wt% |
| 器件24 | 式(1-50) | TPBi | 3:7 | TMDBQA | 15wt% |
| 器件25 | 式(1-51) | Bphen | 4:5 | DPAVB | 5wt% |
| 器件26 | 式(1-55) | Bphen | 5:4 | Rubrene | 5wt% |
| 器件27 | 式(1-60) | TPBi | 6:3 | DCJTB | 5wt% |
| 器件28 | 式(1-65) | BAlq | 7:2 | DBQA | 15wt% |
| 器件29 | 式(1-78) | TmPyPB | 8:1 | DCM2 | 5wt% |
| 器件30 | 式(1-86) | Bphen | 9:1 | Rubrene | 5wt% |
实施例31-45:
本实施例的器件31-45结构如下:
glass/ITO/TADF:空穴传输型材料:磷光材料/cathode
其中TADF:空穴传输型材料:磷光材料采用的材料及所占比例如表3;
其中磷光材料的掺杂浓度是指荧光材料占发光层总重量的比例,即磷光材料的掺杂浓度=磷光材料的质量/(磷光材料的质量+TADF的质量+空穴传输型材料)×100%
表3
实施例46-60:
本实施例的器件46-60结构如下:
glass/ITO/TADF:电子传输型材料:磷光材料/cathode
其中TADF:电子传输型材料:磷光材料采用的材料及所占比例如表4;
其中磷光材料的掺杂浓度是指荧光材料占发光层总重量的比例,即磷光材料的掺杂浓度=磷光材料的质量/(磷光材料的质量+TADF的质量+电子传输型材料)×100%
表4
实施例61-74:
本实施例的器件61-74结构如下:
glass/ITO/TADF:染料/cathode
其中TADF:染料采用的材料及所占比例如表4;
【其中染料请列举至少一个磷光染料或至少一个荧光染料】
表4
| TADF | 染料 | 染料名称 | 染料占比 | |
| 器件61 | 式(1-87) | 荧光 | TMDBQA | 10wt% |
| 器件62 | 式(1-88) | 荧光 | DMQA | 5wt% |
| 器件63 | 式(1-89) | 荧光 | DPAVBi | 5wt% |
| 器件64 | 式(1-90) | 荧光 | BCzVBi | 5wt% |
| 器件65 | 式(1-91) | 荧光 | DCJT | 5wt% |
| 器件66 | 式(1-92) | 荧光 | DCJTB | 5wt% |
| 器件67 | 式(1-93) | 荧光 | Rubrene | 5wt% |
| 器件68 | 式(1-94) | 磷光 | Ir(ppy)3 | 30wt% |
| 器件69 | 式(1-95) | 磷光 | Ir(ppy)2(acac) | 15wt% |
| 器件70 | 式(1-96) | 磷光 | FIrPic | 5wt% |
| 器件71 | 式(1-97) | 磷光 | Ir(2-phq)2(acac) | 15wt% |
| 器件72 | 式(1-98) | 磷光 | Ir(ppy)2(acac) | 30wt% |
| 器件73 | 式(1-99) | 磷光 | Ir(btpy)3 | 20wt% |
| 器件74 | 式(1-100) | 磷光 | Be(pp)2 | 5wt% |
对上述器件4-器件74中的部分器件性能测试结果如下:
| 器件 | 亮度(cd/m2) | 发光效率(cd/A) | 外量子效率(%) | 寿命T90(hrs) |
| 器件4 | 5000 | 20 | 17 | 520 |
| 器件8 | 5000 | 17 | 16 | 498 |
| 器件10 | 1000 | 10 | 4 | 163 |
| 器件12 | 1000 | 9 | 3 | 150 |
| 器件15 | 1000 | 6 | 5 | 155 |
| 器件18 | 1000 | 8 | 5 | 164 |
| 器件20 | 1000 | 8 | 5 | 160 |
| 器件24 | 5000 | 20 | 19 | 392 |
| 器件26 | 5000 | 16 | 17 | 511 |
| 器件30 | 5000 | 17 | 17 | 509 |
| 器件35 | 5000 | 60 | 16 | 398 |
| 器件40 | 1000 | 4 | 6 | 89 |
| 器件48 | 1000 | 4 | 5 | 79 |
| 器件55 | 1000 | 6 | 5 | 80 |
| 器件62 | 5000 | 19 | 17 | 355 |
| 器件68 | 5000 | 57 | 15 | 472 |
| 器件70 | 1000 | 5 | 6 | 74 |
| 器件72 | 5000 | 52 | 14 | 394 |
| 器件74 | 1000 | 7 | 13 | 88 |
有关式(1-85)至式(1-98)所示化合物合成的实施例
实施例75
合成式(1-85)所示结构化合物:在氮气氛围下,将1mol叔丁醇钾溶解到20mlDML中搅拌1小时,然后将溶有1mol咔唑的DML溶液逐滴加入,全部加完后搅拌1小时。随后将溶有0.2mol 2,3,4,5,6-五氟苯腈的DMF溶液逐滴加入,搅拌5小时。随后将反应液倒入水中,过滤得到固体。用色谱柱分离。得式(1-85)所示结构化合物,产率90%。
质谱:929。
元素分析:C:86.60,H:4.35,N:9.05。
实施例76
合成式(1-86)所示结构化合物。反应物咔唑替换为叔丁基咔唑,经过与实施例75相同的合成方法,得式(1-86)所示结构化合物,产率91%。
质谱:1490。
元素分析:C:86.20,H:8.16,N:5.64。
实施例77
合成式(1-87)所示结构化合物。反应物咔唑替换为苯基咔唑,经过与实施例75相同的合成方法,得式(1-87)所示结构化合物,产率91%。
质谱:1689。
元素分析:C:90.20H:4.83N:4.97。
实施例78
合成式(1-88)所示结构化合物。在氮气氛围下,将1mol叔丁醇钾溶解到20mlDML中搅拌1小时,然后将溶有1mol咔唑的DML溶液逐滴加入,全部加完后搅拌1小时。随后将溶有0.25mol 2,3,5,6-四氟苯腈的DMF溶液逐滴加入,搅拌5小时。随后将反应液倒入水中,过滤得到固体。用色谱柱分离。得式(1-88)所示结构化合物,产率90%。
质谱:763。
元素分析:C:86.47,H:4.36,N:9.17。
实施例79
合成式(1-89)所示结构化合物。反应物咔唑替换为叔丁基咔唑,经过与实施例78相同的合成方法,得式(1-89)所示结构化合物,产率91%。
质谱:1212。
元素分析:C:86.15,H:8.07,N:5.77。
实施例80
合成式(1-90)所示结构化合物。反应物咔唑替换为甲基咔唑,经过与实施例78相同的合成方法,得式(1-90)所示结构化合物,产率91%。
质谱:876。
元素分析:C:86.36,H:5.65,N:7.99。
实施例81
合成式(1-91)所示结构化合物。反应物咔唑替换为苯基咔唑,经过与实施例78相同的合成方法,得式(1-91)所示结构化合物,产率91%。
质谱:1372。
元素分析:C:90.10H:4.79N:5.10。
实施例82
合成式(1-92)所示结构化合物。反应物咔唑替换为甲氧基咔唑,经过与实施例78相同的合成方法,得式(1-92)所示结构化合物,产率91%。
质谱:1004。
元素分析:C:75.35H:4.93,N:6.97。
实施例83
合成式(1-93)所示结构化合物。在氮气氛围下,将1mol叔丁醇钾溶解到20mlDML中搅拌1小时,然后将溶有1mol甲氧基咔唑的DML溶液逐滴加入,全部加完后搅拌1小时。随后将溶有0.33mol2,4,6-三氟苯腈的DMF溶液逐滴加入,搅拌5小时。随后将反应液倒入水中,过滤得到固体。用色谱柱分离。得式(1-93)所示结构化合物,产率90%。
质谱:778。
元素分析:C:75.55H:4.93N:7.19。
实施例84
合成式(1-94)所示结构化合物。反应物甲氧基咔唑替换为叔丁基咔唑,经过与实施例83相同的合成方法,得式(1-94)所示结构化合物,产率91%。
质谱:935。
元素分析:C:86.00H:7.81N:5.99。
实施例85
合成式(1-95)所示结构化合物。反应物咔唑替换为吩恶嗪,经过与实施例78相同的合成方法,得式(1-95)所示结构化合物,产率91%。
质谱:829。
元素分析:C:79.79H:4.00N:8.48。
实施例86
合成式(1-96)所示结构化合物。反应物咔唑替换为吩噻嗪,经过与实施例78相同的合成方法,得式(1-96)所示结构化合物,产率91%。
质谱:892。
元素分析:C:74.05,H:3.70N:7.88。
实施例87
合成式(1-97)所示结构化合物。反应物咔唑替换为吖啶,经过与实施例78相同的合成方法,得式(1-97)所示结构化合物,产率91%
质谱:932。
元素分析:C:86.32H:6.15N:7.52。
实施例88
合成式(1-98)所示结构化合物。反应物咔唑替换为吩嗪,经过与实施例78相同的合成方法,得式(1-98)所示结构化合物,产率91%。
质谱:880。
元素分析:C:80.50H:5.17N:14.32
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 (12)
1.一种有机电致发光器件,包括基板,以及依次形成在所述基板上的发光器件,其特征在于,所述发光器件包括第一电极层(1)、发光层(2)和第二电极层(3);所述发光层包括主体材料和染料;
所述主体材料为是由具有空穴传输能力和空穴传输能力的材料构成;
所述主体材料中的至少一种材料的CT激发态的三线态能级T1高于n-π激发态的三线态能级S1,并且T1-S1≤0.3eV;或者,
所述主体材料中的至少一种材料的CT激发态的三线态能级T1高于n-π激发态的三线态能级S1,并且T1-S1≥1eV,并且所述主体材料的n-π激发态的第二三线态能级和CT激发态的第一单线态能级的差值为-0.1~0.1eV。
2.根据权利要求1所述的有机电致发光器件,其特征在于,所述主体材料为激基复合物,所述的激基复合物为热活化延迟荧光材料。
3.根据权利要求1所述的有机电致发光器件,其特征在于,所述主体材料为电子传输型材料和空穴传输型材料构成的激基复合物,二者的质量比为1:9-9:1。
4.根据权利要求3所述的有机电致发光器件,其特征在于,所述电子传输型材料和/或空穴传输型材料的T1-S1≤0.3eV;或电子传输型材料和/或空穴传输型材料的T1-S1≥1eV,并且所述主体材料的n-π激发态的第二三线态能级和CT激发态的第一单线态能级的差值为-0.1~0.1eV。
5.根据权利要求1所述的有机电致发光器件,其特征在于,所述主体材料为热活化延迟荧光材料和空穴传输型材料的组合物,二者的质量比为1:9-9:1。
6.根据权利要求5所述的有机电致发光器件,其特征在于,所述热活化延迟荧光材料和/或空穴传输型材料的T1-S1≤0.3eV;或热活化延迟荧光材料和/或空穴传输型材料的T1-S1≥1eV,并且所述主体材料的n-π激发态的第二三线态能级和CT激发态的第一单线态能级的差值为-0.1~0.1eV。
7.根据权利要求1所述的有机电致发光器件,其特征在于,所述主体材料为热活化延迟荧光材料和电子传输型材料的组合物,二者的质量比为1:9-9:1。
8.根据权利要求7所述的有机电致发光器件,其特征在于,所述热活化延迟荧光材料和/或电子传输型材料的T1-S1≤0.3eV;或热活化延迟荧光材料和/或电子传输型材料的T1-S1≥1eV,并且所述主体材料的n-π激发态的第二三线态能级和CT激发态的第一单线态能级的差值为-0.1~0.1eV。
9.根据权利要求1-7任一所述的有机电致发光器件,其特征在于,所述的染料为荧光材料和/或磷光材料,所述荧光材料的掺杂浓度为0.5-10wt%,所述磷光材料的掺杂浓度为0.5-20wt%。
10.根据权利要求1所述的有机电致发光器件,其特征在于,所述发光层(2)为的厚度为50-150nm。
11.根据权利要求1-10任一所述的有机电致发光器件,其特征在于,
所述电子传输型材料为三(8-羟基喹啉)铝、2,9-二甲基-4,7-二苯基-1,10-邻菲咯啉、4,7-二苯基-1,10-邻菲咯啉、二(2-甲基-8-喹啉基)-4-苯基苯酚铝(III)、1,3,5-三(1-苯基-1H-苯并咪唑-2-基)苯或1,3,5-三[(3-吡啶基)-3-苯基]苯;
空穴传输型材料为N,N’-二-1-萘基)-N,N’-二苯基-1,1’-联苯基-4,4’-二胺、N,N’-二苯基-N,N’-双(间甲基苯基)-1,1’-联苯基-4,4’-二胺、4,4'-环己基二[N,N-二(4-甲基苯基)]苯胺、4,4'-N,N'-二咔唑-联苯、4,4',4”-三(咔唑-9-基)三苯胺或1,3-二咔唑-9-基苯;
所述热活化延迟荧光材料TADF具有式(1-1)-(1-100)所示结构:
12.一种所述的有机电致发光器件的制备方法,包括下述步骤:
在基板上使用开口掩膜板依次蒸镀第一电极层(1),发光层(2)和第二电极层(3);
所述发光层(2)的主体材料和染料采用共蒸镀方式。
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| CN106939000A (zh) * | 2017-02-13 | 2017-07-11 | 太原理工大学 | 基于1,2,4‑三氮唑受体的热激活延迟荧光材料 |
| CN107556310A (zh) * | 2017-09-20 | 2018-01-09 | 石家庄诚志永华显示材料有限公司 | 咪唑衍生物、包含该咪唑衍生物的材料和有机电致发光器件 |
| CN108232022A (zh) * | 2017-12-29 | 2018-06-29 | 南京邮电大学 | 一种有机电致发光器件及其制备方法 |
| WO2018133836A1 (zh) * | 2017-01-20 | 2018-07-26 | 昆山工研院新型平板显示技术中心有限公司 | 一种有机电致发光器件及其制备方法 |
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Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113889586A (zh) * | 2015-07-08 | 2022-01-04 | 株式会社半导体能源研究所 | 发光元件、显示装置、电子设备以及照明装置 |
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| JP2018107449A (ja) * | 2016-12-27 | 2018-07-05 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、電子機器、および照明装置 |
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| JP6770900B2 (ja) * | 2017-01-12 | 2020-10-21 | 日本放送協会 | 有機エレクトロルミネッセンス素子 |
| KR102083093B1 (ko) * | 2017-10-20 | 2020-02-28 | 주식회사 엘지화학 | 유기 발광 소자 |
| EP3490023B1 (en) * | 2017-11-22 | 2020-04-22 | Samsung Electronics Co., Ltd. | Composition, thin film including the composition, and organic light-emitting device including the thin film |
| KR102778193B1 (ko) * | 2017-11-22 | 2025-03-11 | 삼성전자주식회사 | 조성물, 상기 조성물을 포함한 박막 및 이를 포함한 유기 발광 소자 |
| US20210167295A1 (en) * | 2018-04-11 | 2021-06-03 | Nanoco Technologies Ltd. | Electroluminescent display devices and methods of making the same |
| US11367837B2 (en) * | 2018-07-20 | 2022-06-21 | Samsung Electronics Co., Ltd. | Organic light-emitting device |
| JP7252959B2 (ja) | 2018-07-27 | 2023-04-05 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、および電子機器 |
| WO2020059520A1 (ja) * | 2018-09-21 | 2020-03-26 | コニカミノルタ株式会社 | ベンゾニトリル誘導体及びその製造方法、インク組成物、有機エレクトロルミネッセンス素子材料、発光材料、電荷輸送材料、発光性薄膜及び有機エレクトロルミネッセンス素子 |
| US12365678B2 (en) * | 2018-12-18 | 2025-07-22 | Astrazeneca Ab | Pharmaceutical process for the preparation of 4-{4-[(3R)-3-methylmorpholin-4-yl]-6-[1-((R)-S-methylsulfonimidoyl) cyclopropyl]pyrimidin-2-yl}-1H-pyrrolo[2,3-b] pyridine and intermediates |
| CN109713166A (zh) * | 2018-12-21 | 2019-05-03 | 苏州大学 | 一种高效荧光有机发光二极管及其制备方法 |
| US20220190257A1 (en) * | 2019-03-19 | 2022-06-16 | Konica Minolta, Inc. | Functional film, method for forming same, and organic electroluminescent element |
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| US20210119140A1 (en) * | 2019-10-18 | 2021-04-22 | Lg Display Co., Ltd. | Organic light emitting diode and organic light emitting device including the same |
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| KR102875303B1 (ko) * | 2020-09-28 | 2025-10-22 | 엘지디스플레이 주식회사 | 유기발광다이오드 및 유기발광장치 |
| US20220293865A1 (en) * | 2021-03-11 | 2022-09-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN113801102A (zh) * | 2021-10-11 | 2021-12-17 | 上海交通大学 | 基于吩嗪基的化合物及其制备方法与应用 |
| WO2025159172A1 (ja) * | 2024-01-26 | 2025-07-31 | 国立大学法人大阪大学 | 有機電界発光素子 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120298975A1 (en) * | 2002-03-22 | 2012-11-29 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence devices and organic electroluminescence device using the material |
| CN103443949A (zh) * | 2011-03-25 | 2013-12-11 | 出光兴产株式会社 | 有机电致发光器件 |
| TW201510175A (zh) * | 2013-08-14 | 2015-03-16 | Univ Kyushu Nat Univ Corp | 有機電致發光元件 |
| CN104716268A (zh) * | 2013-12-17 | 2015-06-17 | 北京维信诺科技有限公司 | 一种有机电致发光器件及其制备方法 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004058911A2 (de) * | 2002-12-23 | 2004-07-15 | Covion Organic Semiconductors Gmbh | Organisches elektrolumineszenzelement |
| JP4362461B2 (ja) * | 2004-11-05 | 2009-11-11 | 三星モバイルディスプレイ株式會社 | 有機電界発光素子 |
| EP2080762B1 (en) * | 2006-11-09 | 2016-09-14 | Nippon Steel & Sumikin Chemical Co., Ltd. | Compound for organic electroluminescent device and organic electroluminescent device |
| WO2009136596A1 (ja) * | 2008-05-08 | 2009-11-12 | 新日鐵化学株式会社 | 有機電界発光素子 |
| US8632893B2 (en) * | 2008-07-22 | 2014-01-21 | Industrial Technology Research Institute | Organic compound and organic electroluminescence device employing the same |
| WO2010098246A1 (ja) * | 2009-02-27 | 2010-09-02 | 新日鐵化学株式会社 | 有機電界発光素子 |
| US9299947B2 (en) * | 2009-03-31 | 2016-03-29 | Nippon Steel & Sumikin Chemical Co., Ltd. | Organic electroluminescent device having an electron- and /or exciton-blocking layer comprising an indolocarbazole compound |
| CN101993440B (zh) | 2009-08-25 | 2012-07-25 | 中国科学院化学研究所 | 基于联苯并噻二唑的多臂共轭分子及其制备方法和应用 |
| WO2011132684A1 (ja) * | 2010-04-20 | 2011-10-27 | 出光興産株式会社 | ビスカルバゾール誘導体、有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
| US9954180B2 (en) * | 2010-08-20 | 2018-04-24 | Universal Display Corporation | Bicarbazole compounds for OLEDs |
| TWI549942B (zh) | 2010-08-26 | 2016-09-21 | 首威公司 | N-苯基三咔唑類 |
| JP2015135836A (ja) * | 2012-03-29 | 2015-07-27 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子および有機エレクトロルミネッセンス素子用材料 |
| JP5594750B2 (ja) * | 2012-05-17 | 2014-09-24 | 国立大学法人九州大学 | 化合物、発光材料および有機発光素子 |
| ES2707628T3 (es) | 2012-06-29 | 2019-04-04 | Airbus Operations Sl | Larguerillo en forma de "t" con extremo del alma redondeado y su método de fabricación |
| US10991892B2 (en) * | 2012-07-23 | 2021-04-27 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| KR101617877B1 (ko) | 2013-01-16 | 2016-05-03 | 서울대학교산학협력단 | 유기발광다이오드 |
| WO2014157610A1 (ja) * | 2013-03-29 | 2014-10-02 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、照明装置、表示装置、有機ルミネッセンス素子用発光性薄膜と組成物及び発光方法 |
| US10141520B2 (en) * | 2013-04-05 | 2018-11-27 | Konica Minolta, Inc. | Coating liquid for forming light emitting layer, organic electroluminescent element, method for manufacturing organic electroluminescent element, and lighting/display device |
| US9365921B2 (en) | 2013-06-28 | 2016-06-14 | Semiconductor Energy Laboratory Co., Ltd. | Method for fabricating light-emitting element using chamber with mass spectrometer |
| KR20160039625A (ko) | 2013-08-09 | 2016-04-11 | 이데미쓰 고산 가부시키가이샤 | 유기 전기발광용 조성물, 유기 전기발광 소자용 재료, 유기 전기발광 소자용 재료 용액 및 유기 전기발광 소자 |
| JP5994753B2 (ja) * | 2013-08-19 | 2016-09-21 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、それに用いる蛍光発光性化合物、当該有機エレクトロルミネッセンス素子を具備する照明装置及び表示装置 |
| US9312498B2 (en) | 2013-09-12 | 2016-04-12 | Semiconductor Energy Laboratory Co., Ltd. | Organic compound, light-emitting element, display module, lighting module, light-emitting device, display device, electronic appliance, and lighting device |
| CN105794321B (zh) * | 2013-12-02 | 2018-05-22 | 株式会社半导体能源研究所 | 发光元件、显示模块、照明模块、发光装置、显示装置、电子设备以及照明装置 |
-
2015
- 2015-06-16 CN CN201510334281.9A patent/CN106328816B/zh active Active
-
2016
- 2016-06-15 JP JP2017564638A patent/JP6595627B2/ja active Active
- 2016-06-15 US US15/737,179 patent/US11437582B2/en active Active
- 2016-06-15 WO PCT/CN2016/085802 patent/WO2016202251A1/zh not_active Ceased
- 2016-06-15 TW TW105118809A patent/TWI634813B/zh active
- 2016-06-15 KR KR1020187000314A patent/KR102015772B1/ko active Active
- 2016-06-15 EP EP16810992.4A patent/EP3312897B1/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120298975A1 (en) * | 2002-03-22 | 2012-11-29 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence devices and organic electroluminescence device using the material |
| CN103443949A (zh) * | 2011-03-25 | 2013-12-11 | 出光兴产株式会社 | 有机电致发光器件 |
| TW201510175A (zh) * | 2013-08-14 | 2015-03-16 | Univ Kyushu Nat Univ Corp | 有機電致發光元件 |
| CN104716268A (zh) * | 2013-12-17 | 2015-06-17 | 北京维信诺科技有限公司 | 一种有机电致发光器件及其制备方法 |
Non-Patent Citations (2)
| Title |
|---|
| YOUNG-SEO PARK等: "Exciplex-Forming Co-host for Organic Light-Emitting Diodes with Ultimate Efficiency", 《ADV. FUNCT. MATER.》 * |
| 杨兵等: "新一代有机电致发光材料突破激子统计", 《中国科学: 化学》 * |
Cited By (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12365835B2 (en) | 2015-08-07 | 2025-07-22 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, display device, electronic device, and lighting device |
| CN106220649B (zh) * | 2016-04-25 | 2018-07-24 | 中节能万润股份有限公司 | 一种基于二芳基酮的化合物及其在有机电致发光器件上的应用 |
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| US12289991B2 (en) | 2017-01-19 | 2025-04-29 | Samsung Display Co., Ltd. | Organic electroluminescence device |
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| CN108336237A (zh) * | 2017-01-20 | 2018-07-27 | 昆山工研院新型平板显示技术中心有限公司 | 一种有机电致发光器件 |
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| US11158821B2 (en) | 2017-01-20 | 2021-10-26 | Kunshan New Flat Panel Display Technology Center Co., Ltd. | Organic electroluminescent device and manufacturing method thereof |
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| CN108530357A (zh) * | 2017-03-03 | 2018-09-14 | 中国科学院宁波材料技术与工程研究所 | 吖啶类d-a型热活化延迟荧光材料、其制备方法及应用 |
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| US11557731B2 (en) | 2018-12-27 | 2023-01-17 | Lg Display Co., Ltd. | Organic light emitting diode having n-type host with narrow band gap and organic light emitting display device including the same |
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| CN109678851A (zh) * | 2019-01-31 | 2019-04-26 | 武汉华星光电半导体显示技术有限公司 | 热激活延迟荧光材料、有机电致发光器件及显示面板 |
| CN110183361A (zh) * | 2019-06-12 | 2019-08-30 | 常州大学 | ‘十字架’型热活性延迟荧光材料的构筑及其应用 |
| CN110437135A (zh) * | 2019-08-12 | 2019-11-12 | 三明学院 | D-a-d’型荧光化合物及合成、应用 |
| CN110627821A (zh) * | 2019-09-29 | 2019-12-31 | 上海天马有机发光显示技术有限公司 | 一种化合物、有机电致发光器件、显示面板及显示装置 |
| CN111916570B (zh) * | 2020-06-23 | 2021-08-06 | 华南理工大学 | 一种tadf敏化的荧光有机发光二极管及其制备方法 |
| CN111916570A (zh) * | 2020-06-23 | 2020-11-10 | 华南理工大学 | 一种热活化延迟荧光敏化的荧光有机发光二极管及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20180015242A (ko) | 2018-02-12 |
| KR102015772B1 (ko) | 2019-08-29 |
| EP3312897A1 (en) | 2018-04-25 |
| TW201701727A (zh) | 2017-01-01 |
| EP3312897B1 (en) | 2023-12-27 |
| JP2018519663A (ja) | 2018-07-19 |
| WO2016202251A1 (zh) | 2016-12-22 |
| TWI634813B (zh) | 2018-09-01 |
| CN106328816B (zh) | 2018-11-13 |
| JP6595627B2 (ja) | 2019-10-23 |
| US20180175294A1 (en) | 2018-06-21 |
| EP3312897A4 (en) | 2019-04-03 |
| US11437582B2 (en) | 2022-09-06 |
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