CN111777516A - 一种有机发光化合物及其制备方法和应用 - Google Patents
一种有机发光化合物及其制备方法和应用 Download PDFInfo
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- CN111777516A CN111777516A CN202010735141.3A CN202010735141A CN111777516A CN 111777516 A CN111777516 A CN 111777516A CN 202010735141 A CN202010735141 A CN 202010735141A CN 111777516 A CN111777516 A CN 111777516A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 99
- 238000002360 preparation method Methods 0.000 title claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- -1 nitro, amino, hydroxy Chemical group 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 60
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 28
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 238000001556 precipitation Methods 0.000 claims description 15
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims description 14
- 238000004440 column chromatography Methods 0.000 claims description 14
- 230000005525 hole transport Effects 0.000 claims description 13
- 238000001816 cooling Methods 0.000 claims description 9
- 239000002244 precipitate Substances 0.000 claims description 9
- 239000000376 reactant Substances 0.000 claims description 8
- 238000000967 suction filtration Methods 0.000 claims description 5
- 238000002386 leaching Methods 0.000 claims description 4
- 229940126062 Compound A Drugs 0.000 claims description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 18
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 41
- 238000000921 elemental analysis Methods 0.000 description 10
- 238000002347 injection Methods 0.000 description 10
- 239000007924 injection Substances 0.000 description 10
- 238000001819 mass spectrum Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 7
- 238000001514 detection method Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 101100490479 Lactococcus lactis subsp. lactis (strain IL1403) addA gene Proteins 0.000 description 2
- 101100000975 Lactococcus lactis subsp. lactis (strain IL1403) rexB gene Proteins 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
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- 239000011248 coating agent Substances 0.000 description 1
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- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
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Abstract
Description
技术领域
本发明属于化学合成及光电材料领域,涉及一种P型掺杂空穴注入化合物及其应用。
背景技术
有机发光现象是指利用有机物质将电能转换为光能的现象。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。有机物层为了提高有机电气元件的效率和稳定性而普遍形成为由各种不同物质构成的多层结构,例如,能够由空穴注入层、空穴输送层、发光层、电子输送层及电子注入层等形成。
目前,随着便携式显示器市场中显示器尺寸变得越来越大,功耗也越来越多。功耗由此成为便携式显示器有限电池电源中亟需解决的问题,除此之外,还需要解决电池效率和寿命问题。
效率,寿命,驱动电压等彼此相关。例如,如果提高效率,则驱动电压相对降低,并且随着驱动电压降低,由于操作期间产生的焦耳热而导致的有机材料的结晶减少,结果寿命显示出增加的趋势。然而,仅通过简单地改善有机材料层并不能得到最大化效率。
此外,为了解决最近的有机电子元件中的空穴传输层的发光问题,在空穴传输层和发光层之间存在发光辅助层。
通常,从电子传输层转移到发光层的电子和从空穴传输层转移到发光层的空穴重新结合以形成激子。由于空穴传输层中使用的材料应具有低HOMO值,因此其主要具有低T1值。从而导致从发光层产生的激子被传输到空穴传输层,使发光层中的电荷不平衡,发光在空穴传输层中或在空穴传输层的界面处发生,最终使得有机发光器件的色纯度,效率和寿命降低。
而且,当使用具有快速空穴迁移率的材料来降低驱动电压时,这倾向于降低效率。在OLED中,由于空穴迁移率比电子迁移率快,导致发光层中的电荷不平衡,从而会降低其效率和寿命。
但仅仅通过关于发光辅助层材料的核心的结构特征不满足这些要求,发光辅助层必须由能够解决空穴传输层问题的材料形成,该材料需要具有合适的空穴迁移率以提供合适的驱动电压,高T1能量值和宽带隙。因此,需要开发具有高T1能量值和宽带隙的有机物层的材料,以提高有机电子元件的效率和寿命。
发明内容
本发明的目的在于提供一种有机发光化合物,以解决上述背景技术中提出的问题。
为了达到上述目的,本发明采用如下技术方案:
一种有机发光化合物,所述有机发光化合物的结构通式为式I:
式I中,Ar1、Ar2、Ar3、Ar4分别独立地选自C6~C30芳基或C3~C30芳族杂环基;
R1和R2分别独立地选自氢、氘、硝基、氨基、羟基、卤素、氰基、巯基、烷基、烷氧基、烯烃基、炔烃基、芳基或芳族杂环基。
优选的,所述R1和R2分别独立地选自氢、氘、硝基、氨基、羟基、卤素、氰基、巯基、C1~C8烷基、C1~C8烷氧基、C2~C6烯烃基、C2~C6炔烃基、C6~C18芳基或C4~C12芳族杂环基。
优选的,所述芳基为取代或未取代的芳基;所述芳族杂环基为取代或未取代的芳族杂环基。
优选的,所述烷基为取代或未取代的直链烷基、支链烷基或环烷基。
优选的,所述取代的基团选自氘、硝基、氨基、羟基、卤素、氰基、羰基或巯基。
优选的,所述有机发光化合物的化学结构式为式L001~式L096中的一种:
本发明还公开了上述有机发光化合物的制备方法,包括以下步骤:
在氮气保护气氛下,将反应物a、反应物b、三(二亚苄基丙酮)二钯、三叔丁基膦、叔丁醇钠置于反应体系中,并加入甲苯,在120℃的条件下反应10小时,然后冷却到室温,待沉淀析出后抽滤,用柱层析提纯,得到中间体1;
将中间体1、化合物c、三(二亚苄基丙酮)二钯、三叔丁基膦、叔丁醇钠置于反应体系中,并加入甲苯,在氮气保护以及120℃的条件下反应10小时,然后冷却到室温,待沉淀析出后抽滤,用柱层析提纯,得到式1化合物,即为有机发光化合物;
上述方法中所述步骤(1)中所述化合物a与所述化合物b的摩尔质量比为1:(0.8~1);所述甲苯的体积与所述化合物a的质量比为100~150ml:8~10g;步骤(2)中所述中间体1与所述化合物c的摩尔质量比为1:(0.8~1);所述甲苯的体积与所述中间体1的质量比为100~150ml:8~10g。
本发明还提供了上述有机发光化合物的另一种制备方法,包括以下步骤:
在氮气保护气氛下,将反应物A、反应物b、三(二亚苄基丙酮)二钯、三叔丁基膦、叔丁醇钠按一定比例置于反应体系中,并加入甲苯,在氮气保护以及120℃的条件下反应10小时,然后冷却到室温,待沉淀析出后,将沉淀抽滤,用柱层析提纯,得到式1化合物,即为有机发光化合物;
上述方法中所述步骤(1)中所述化合物A与所述化合物b的摩尔质量比为1:(2~2.2);所述甲苯的体积与所述化合物A的质量比为100~150ml:8~10g。
与现有技术相比,本发明提供了一种新的有机发光化合物,本发明提供的有机发光化合物的合成路线较短,工艺简单,原料易得,成本低,适合工业化生产。并且,使用本发明提供的有机发光材料所制得的有机电致发光器件,其驱动电压明显降低,发光效率以及寿命得到显著提高。
具体实施方式
下面将对本发明实施例中的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
实施例1
该实施例提供了一种有机发光化合物,其化学结构式为发明内容中的式L001,该有机发光化合物的制备方法的反应路线如下:
其具体的制备方法包括以下步骤:
在氮气保护气氛下,称取式001-A所示的化合物(22.5mmol,10.00g)、001-B所示的化合物(49.5mmo1,8.38g)、三(二亚苄基丙酮)二钯(0.23mmol,0.21g)、三叔丁基膦(0.50mmol,0.21g)、叔丁醇钠(90mmol,8.65g)置于反应体系中,并加入100mL甲苯,在氮气保护以及120℃的条件下反应10小时,然后冷却到室温,待沉淀析出后,将沉淀抽滤,用柱层析(柱高6cm)提纯,得到化合物L001,即为有机发光化合物(8.66g,产率为62%)。
将该有机发光化合物用HPLC检测纯度为99.8%;另外,该有机发光化合物质谱计算值为620.84,质谱测试值为621.51,其元素分析的计算值为:C:88.99%;H:6.49%;N:4.51%;元素分析的测试值为:C:88.98%;H:6.50%;N:4.52%。
实施例2
该实施例提供了一种有机发光化合物,其化学结构式为发明内容中的式L045,该有机发光化合物的制备方法的反应路线如下:
其具体的制备方法包括以下步骤:
(1)在氮气保护气氛下,称取式045-A所示的化合物(22.5mmol,8.99g)、045-B所示的化合物(22.5mmo1,6.42g)、三(二亚苄基丙酮)二钯(0.12mmol,0.11g)、三叔丁基膦(0.25mmol,0.12g)、叔丁醇钠(45mmol,4.33g)置于反应体系中,并加入80mL甲苯,在氮气保护以及120℃的条件下反应10小时,然后冷却到室温,待沉淀析出后,将沉淀抽滤,用柱层析(柱高6cm)提纯,得到中间体045-1(10.19g,产率为75%)。
(2)将中间体045-1(16.5mmol,9.96g)、045-C所示的化合物(24.75mmol,4.18g)、三(二亚苄基丙酮)二钯(0.12mmol,0.11g)、三叔丁基膦(0.25mmol,0.12g)、叔丁醇钠(45mmol,4.33g)置于反应体系中,并加入80mL甲苯,在氮气保护以及120℃的条件下反应10小时,然后冷却到室温,待沉淀析出后,将沉淀抽滤,用柱层析(柱高6cm)提纯,得到化合物L045,即为有机发光化合物(10.3g,产率为85%)。
将该有机发光化合物用HPLC检测纯度为99.8%;另外,该有机发光化合物质谱计算值为737.00,质谱测试值为738.12,其元素分析的计算值为:C:89.63%;H:6.56%;N:3.80%;元素分析的测试值为:C:89.62%;H:6.55%;N:3.81%。
实施例3
该实施例提供了一种有机发光化合物,其化学结构式为发明内容中的式L065,该有机发光化合物的制备方法的反应路线如下:
其具体的制备方法包括以下步骤:
在氮气保护气氛下,称取式065-A所示的化合物(22.5mmol,10.55g)、065-B所示的化合物(49.5mmo1,8.38g)、三(二亚苄基丙酮)二钯(0.23mmol,0.21g)、三叔丁基膦(0.50mmol,0.21g)、叔丁醇钠(90mmol,8.65g)置于反应体系中,并加入100mL甲苯,在氮气保护以及120℃的条件下反应10小时,然后冷却到室温,待沉淀析出后,将沉淀抽滤,用柱层析(柱高6cm)提纯,得到化合物L065,即为有机发光化合物(11.33g,产率为78%)。
将该有机发光化合物用HPLC检测纯度为99.8%;另外,该有机发光化合物质谱计算值为645.85,质谱测试值为646.77,其元素分析的计算值为:C:87.41%;H:6.09%;N:6.51%;元素分析的测试值为:C:87.41%;H:6.09%;N:6.51%。
实施例4
该实施例提供了一种有机发光化合物,其化学结构式为发明内容中的式L078,该有机发光化合物的制备方法的反应路线如下:
其具体的制备方法包括以下步骤:
(1)在氮气保护气氛下,称取式078-A所示的化合物(22.5mmol,8.99g)、078-B所示的化合物(22.5mmo1,5.52g)、三(二亚苄基丙酮)二钯(0.12mmol,0.11g)、三叔丁基膦(0.25mmol,0.12g)、叔丁醇钠(45mmol,4.33g)置于反应体系中,并加入80mL甲苯,在氮气保护以及120℃的条件下反应10小时,然后冷却到室温,待沉淀析出后,将沉淀抽滤,用柱层析(柱高6cm)提纯,得到中间体078-1(11.00g,产率为83%)。
(2)将中间体078-1(16.5mmol,9.72g)、078-C所示的化合物(24.75mmol,4.18g)、三(二亚苄基丙酮)二钯(0.12mmol,0.11g)、三叔丁基膦(0.25mmol,0.12g)、叔丁醇钠(45mmol,4.33g)置于反应体系中,并加入80mL甲苯,在氮气保护以及120℃的条件下反应10小时,然后冷却到室温,待沉淀析出后,将沉淀抽滤,用柱层析(柱高6cm)提纯,得到化合物L078,即为有机发光化合物(9.76g,产率为82%)。
将该有机发光化合物用HPLC检测纯度为99.8%;另外,该有机发光化合物质谱计算值为721.95,质谱测试值为722.78,其元素分析的计算值为:C:88.18%;H:6.00%;N:5.82%;元素分析的测试值为:C:88.17%;H:6.01%;N:5.83%。
实施例5
该实施例提供了一种有机发光化合物,其化学结构式为发明内容中的式L090,该有机发光化合物的制备方法的反应路线如下:
其具体的制备方法包括以下步骤:
(1)在氮气保护气氛下,称取式090-A所示的化合物(22.5mmol,10.70g)、090-B所示的化合物(22.5mmo1,5.52g)、三(二亚苄基丙酮)二钯(0.12mmol,0.11g)、三叔丁基膦(0.25mmol,0.12g)、叔丁醇钠(45mmol,4.33g)置于反应体系中,并加入80mL甲苯,在氮气保护以及120℃的条件下反应10小时,然后冷却到室温,待沉淀析出后,将沉淀抽滤,用柱层析(柱高6cm)提纯,得到中间体090-1(11.81g,产率为82%)。
(2)将中间体090-1(16.5mmol,10.56g)、090-C所示的化合物(24.75mmol,4.18g)、三(二亚苄基丙酮)二钯(0.12mmol,0.11g)、三叔丁基膦(0.25mmol,0.12g)、叔丁醇钠(45mmol,4.33g)置于反应体系中,并加入80mL甲苯,在氮气保护以及120℃的条件下反应10小时,然后冷却到室温,待沉淀析出后,将沉淀抽滤,用柱层析(柱高6cm)提纯,得到化合物L090,即为有机发光化合物(10.58g,产率为83%)。
将该有机发光化合物用HPLC检测纯度为99.8%;另外,该有机发光化合物质谱计算值为773.04,质谱测试值为774.21,其元素分析的计算值为:C:90.12%;H:6.26%;N:3.62%;元素分析的测试值为:C:90.13%;H:6.25%;N:3.61%。
因结构通式为发明内容中式I的其他化合物的制备方法的合成路线和原理均与上述所列举的实施例1~5的相同,所以在此不再列举,本发明又选取10个化合物(发明内容中的式L012、L025、L028、L041、L057、L063、L073、L081、L084、L093)做为实施例6-15,其对应质谱测试值和分子式如下表1所示。
表1:实施例6-15制备的化合物的分子式和质谱测试值
器件实施例1
该实施例提供了一种有机电致发光器件的制备方法,其包括以下步骤:
(1)将涂层厚度为的ITO玻璃基板放在蒸馏水中清洗2次,超声波洗涤30分钟,用蒸馏水反复清洗2次,超声波洗涤10分钟,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5分钟,接着,将ITO衬底安装在真空气相沉积设备的衬底夹持器上。将HI001引入到所述真空气相沉积设备的单元中,并且随后将所述设备的腔室中的压力控制为10-7托。此后,向所述单元施加电流以蒸发上述引入的材料,由此在ITO衬底上形成厚度为的第一空穴注入层。接着,将HAT-CN引入所述真空气相沉积设备的另一单元中,且通过向所述单元施加电流蒸发,由此在第一空穴注入层上形成厚度为的第二空穴注入层。接着,将如下的化合物NPB引入到真空气相沉积设备的另一单元中,且通过向所述单元施加电流蒸发,由此在第二空穴注入层上形成厚度为的第一空穴传输层。接着,将化合物L001引入到真空气相沉积设备的另一单元中,且通过向所述单元施加电流蒸发,由此在第一空穴传输层上形成厚度为的第二空穴传输层。此后,将化合物RH001引入到真空气相沉积设备的一个单元中作为主体,并且将化合物Ir(piq)2acac中的一种引入到另一个单元中作为掺杂剂。两种材料以不同速率蒸发且以按主体和掺杂剂的总量计重量3%的掺杂量沉积以在第二空穴传输层上形成厚度为的发光层。随后,将ET001引入到一个单元中,并且Liq引入到另一单元中。使两种材料以相同速率蒸发,并且各自以50重量%的掺杂量沉积,以在发光层上形成厚度为的电子输送层。随后,将Liq在电子传输层上沉积成厚度为的电子注入层之后,通过另一个真空气相沉积设备在电子注入层上沉积厚度为的Al阴极。由此,即可得到有机电致发光器件。用于制造OLED装置的所有材料在使用之前都通过在10-4托下真空升华而纯化。
其中,第一空穴注入层化合物HI001和第二空穴注入层化合物HAT-CN结构式为:
其中,第一空穴传输层化合物物NPB结构式为;
其中,主体物质化合物RH001和掺杂物质化合物Ir(piq)2acac的结构式为:
其中,电子传输层ET001和电子传输层和电子注入层Liq的化合物结构式为
参照上述器件实施例1提供的方法,分别选用化学结构式为式L012、L025、L028、L041、L045、L057、L063、L065、L073、L078、L081、L084、L090、L093的有机发光材料替代结构式为式L001的有机发光材料进行蒸镀,作为器件实施例2-15,并制备得到相应的有机电致发光器件。
对比例1
该对比例提供了一种有机电致发光器件,该有机电致发光器件的制备方法与实施例6的唯一区别在于,该有机电致发光器件的是采用现有有机化合物H T002替代L001进行蒸镀。
其中HT002化合物的结构式为:
将上述器件实施例1-15和对比例1得到的有机电致发光器件分别采用KE ITHLEY2400型源测量单元和PR670分光辐射亮度计及寿命测试仪测试其驱动电压、发光效率以及T95寿命等性能,其测试结果如下表2所示。
表2
从上表2可以看出,使用本发明实施例提供的有机发光材料所制得的有机电致发光器件,其驱动电压明显降低,发光效率以及寿命得到显著提高。
本说明书中各个实施例采用递进的方式描述,每个实施例重点说明的都是与其他实施例的不同之处,各个实施例之间相同相似部分互相参见即可。
对所公开的实施例的上述说明,使本领域专业技术人员能够实现或使用本发明。对这些实施例的多种修改对本领域的专业技术人员来说将是显而易见的,本文中所定义的一般原理可以在不脱离本发明的精神或范围的情况下,在其它实施例中实现。因此,本发明将不会被限制于本文所示的这些实施例,而是要符合与本文所公开的原理和新颖特点相一致的最宽的范围。
Claims (10)
2.根据权利要求1所述的一种有机发光化合物,其特征在于,所述R1和R2分别独立地选自氢、氘、硝基、氨基、羟基、卤素、氰基、巯基、C1~C8烷基、C1~C8烷氧基、C2~C6烯烃基、C2~C6炔烃基、C6~C18芳基或C4~C12芳族杂环基。
3.根据权利要求1所述的一种有机发光化合物,其特征在于,所述芳基为取代或未取代的芳基;所述芳族杂环基为取代或未取代的芳族杂环基。
4.根据权利要求1所述的一种有机发光化合物,其特征在于,所述烷基为取代或未取代的直链烷基、支链烷基或环烷基。
5.根据权利要求3或4所述的一种有机发光化合物,其特征在于,所述取代的基团选自氘、硝基、氨基、羟基、卤素、氰基、羰基或巯基。
8.根据权利要求6所述的一种有机发光化合物的制备方法,其特征在于,所述步骤(1)中所述化合物a与所述化合物b的摩尔质量比为1:(0.8~1);所述甲苯的体积与所述化合物a的质量比为100~150ml:8~10g;步骤(2)中所述中间体1与所述化合物c的摩尔质量比为1:(0.8~1);所述甲苯的体积与所述中间体1的质量比为100~150ml:8~10g。
9.根据权利要求7所述的一种有机发光化合物的制备方法,其特征在于,所述步骤(1)中所述化合物A与所述化合物b的摩尔质量比为1:(2~2.2);所述甲苯的体积与所述化合物a的质量比为100~150ml:8~10g。
10.权利要求1-5任一项所述的一种有机发光化合物在制备空穴传输层中应用。
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WO2021164572A1 (zh) * | 2020-02-17 | 2021-08-26 | 陕西莱特光电材料股份有限公司 | 含氮化合物、电子元件和电子装置 |
CN114478269A (zh) * | 2020-11-13 | 2022-05-13 | 广州华睿光电材料有限公司 | 有机化合物、混合物、组合物及有机电子器件 |
WO2022169201A1 (ko) * | 2021-02-08 | 2022-08-11 | 주식회사 엘지화학 | 아민계 화합물 및 이를 포함하는 유기 발광 소자 |
CN115504889A (zh) * | 2021-06-07 | 2022-12-23 | 陕西莱特迈思光电材料有限公司 | 含氮化合物、电子元件和电子装置 |
CN116444467A (zh) * | 2023-06-19 | 2023-07-18 | 吉林奥来德光电材料股份有限公司 | 一种发光辅助材料及其制备方法、有机电致发光器件 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110128279A (zh) * | 2019-06-14 | 2019-08-16 | 陕西莱特光电材料股份有限公司 | 有机电致发光材料及包含该材料的有机电致发光器件 |
CN110183332A (zh) * | 2019-06-17 | 2019-08-30 | 陕西莱特光电材料股份有限公司 | 一种包含多环烷烃的芳香族衍生物及包含该衍生物的有机电致发光器件 |
WO2020050623A1 (ko) * | 2018-09-04 | 2020-03-12 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기발광 소자 |
KR20200037732A (ko) * | 2018-10-01 | 2020-04-09 | 머티어리얼사이언스 주식회사 | 유기 화합물 및 이를 포함하는 유기전계발광소자 |
WO2020080872A1 (ko) * | 2018-10-18 | 2020-04-23 | 주식회사 엘지화학 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
CN111138298A (zh) * | 2019-12-31 | 2020-05-12 | 陕西莱特光电材料股份有限公司 | 含氮化合物、电子元件和电子装置 |
CN111892505A (zh) * | 2020-02-17 | 2020-11-06 | 陕西莱特光电材料股份有限公司 | 含氮化合物、电子元件和电子装置 |
-
2020
- 2020-07-28 CN CN202010735141.3A patent/CN111777516B/zh active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020050623A1 (ko) * | 2018-09-04 | 2020-03-12 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기발광 소자 |
KR20200037732A (ko) * | 2018-10-01 | 2020-04-09 | 머티어리얼사이언스 주식회사 | 유기 화합물 및 이를 포함하는 유기전계발광소자 |
WO2020080872A1 (ko) * | 2018-10-18 | 2020-04-23 | 주식회사 엘지화학 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
CN110128279A (zh) * | 2019-06-14 | 2019-08-16 | 陕西莱特光电材料股份有限公司 | 有机电致发光材料及包含该材料的有机电致发光器件 |
CN110183332A (zh) * | 2019-06-17 | 2019-08-30 | 陕西莱特光电材料股份有限公司 | 一种包含多环烷烃的芳香族衍生物及包含该衍生物的有机电致发光器件 |
CN111138298A (zh) * | 2019-12-31 | 2020-05-12 | 陕西莱特光电材料股份有限公司 | 含氮化合物、电子元件和电子装置 |
CN111892505A (zh) * | 2020-02-17 | 2020-11-06 | 陕西莱特光电材料股份有限公司 | 含氮化合物、电子元件和电子装置 |
Non-Patent Citations (2)
Title |
---|
CHING-HSIN,等: "Synthesis and characterization of spiro(adamantane-2,9"-fluorene)-based triaryldiamines: thermally stable hole-transporting materials", 《SYNTHETIC METALS》 * |
刘涛平,等: "三芳胺合成的研究进展", 《有机化学》 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021164572A1 (zh) * | 2020-02-17 | 2021-08-26 | 陕西莱特光电材料股份有限公司 | 含氮化合物、电子元件和电子装置 |
CN114478269A (zh) * | 2020-11-13 | 2022-05-13 | 广州华睿光电材料有限公司 | 有机化合物、混合物、组合物及有机电子器件 |
CN114478269B (zh) * | 2020-11-13 | 2024-02-02 | 广州华睿光电材料有限公司 | 有机化合物、混合物、组合物及有机电子器件 |
WO2022169201A1 (ko) * | 2021-02-08 | 2022-08-11 | 주식회사 엘지화학 | 아민계 화합물 및 이를 포함하는 유기 발광 소자 |
CN115504889A (zh) * | 2021-06-07 | 2022-12-23 | 陕西莱特迈思光电材料有限公司 | 含氮化合物、电子元件和电子装置 |
CN115504889B (zh) * | 2021-06-07 | 2023-12-08 | 陕西莱特迈思光电材料有限公司 | 含氮化合物、电子元件和电子装置 |
CN116444467A (zh) * | 2023-06-19 | 2023-07-18 | 吉林奥来德光电材料股份有限公司 | 一种发光辅助材料及其制备方法、有机电致发光器件 |
CN116444467B (zh) * | 2023-06-19 | 2023-10-13 | 吉林奥来德光电材料股份有限公司 | 一种发光辅助材料及其制备方法、有机电致发光器件 |
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