CN111848562A - 有机电致发光材料及其应用 - Google Patents
有机电致发光材料及其应用 Download PDFInfo
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- CN111848562A CN111848562A CN201910339412.0A CN201910339412A CN111848562A CN 111848562 A CN111848562 A CN 111848562A CN 201910339412 A CN201910339412 A CN 201910339412A CN 111848562 A CN111848562 A CN 111848562A
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- 239000000463 material Substances 0.000 title claims abstract description 79
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- 150000001875 compounds Chemical class 0.000 claims description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- -1 amine compound Chemical class 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
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- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
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- 150000002910 rare earth metals Chemical class 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 abstract description 9
- 238000005401 electroluminescence Methods 0.000 abstract description 5
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 abstract description 4
- 230000005012 migration Effects 0.000 abstract description 4
- 238000013508 migration Methods 0.000 abstract description 4
- 125000003277 amino group Chemical group 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 51
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- 230000015572 biosynthetic process Effects 0.000 description 30
- 238000003786 synthesis reaction Methods 0.000 description 30
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 28
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 26
- 238000004128 high performance liquid chromatography Methods 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
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- 229910052757 nitrogen Inorganic materials 0.000 description 16
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 101000806846 Homo sapiens DNA-(apurinic or apyrimidinic site) endonuclease Proteins 0.000 description 2
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- 230000000052 comparative effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
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- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- 101100219315 Arabidopsis thaliana CYP83A1 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 101100269674 Mus musculus Alyref2 gene Proteins 0.000 description 1
- 101100140580 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) REF2 gene Proteins 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- KYKLWYKWCAYAJY-UHFFFAOYSA-N oxotin;zinc Chemical compound [Zn].[Sn]=O KYKLWYKWCAYAJY-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
本发明提供一种有机电致发光材料及其应用,有机电致发光材料包含二苯并呋喃或二苯并噻吩基团且为不对称胺结构,具有较高的溶解能力、较高的空穴迁移能力及较好的稳定性,可以被应用在有机电致发光领域,作为空穴注入传输材料使用,从而可提高OLED器件的性能,扩大OLED器件的应用范围。
Description
技术领域
本发明属于有机电致发光技术领域,涉及有机电致发光材料及其应用。
背景技术
有机电致发光(Organic Light-Emitting Diode,OLED)材料在信息显示材料、有机光电子材料等领域中的应用具有极大的研究价值和美好的应用前景。随着多媒体信息技术的发展,对平板显示器件性能的要求越来越高。目前主要的显示技术有等离子显示器件、场发射显示器件和有机电致发光显示器件。其中,有机电致发光显示器件由于具有自发光、广视角、几乎无穷高的对比度、较低耗电、极高反应速度、颜色丰富等一系列优点,被视为21世纪最具前途的产品之一。
当前,OLED显示技术已经在智能手机、电脑、穿戴配饰等领域获得应用,进一步还将向电视等大尺寸应用领域扩展。但是,和实际的产品应用要求相比,OLED器件的发光效率,使用寿命等性能还需要进一步提升。
对于OLED器件提高性能的研究主要包括:降低器件的驱动电压,提高器件的发光效率,提高器件的使用寿命等。为了实现OLED器件的性能的不断提升,不但需要从OLED器件结构和制作工艺进行创新,更需要对OLED光电功能材料进行不断的研究和创新。
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,即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和空穴注入传输材料;将发光材料分为主体发光材料和掺杂材料。
目前报道的空穴注入传输材料,溶解能力较低、空穴迁移能力较低、稳定性较差,因此增加了制备工艺的难度,难以提高OLED器件的性能。
因此,提供一种新型、具有较高的溶解能力、较高的空穴迁移能力及较好的稳定性的有机电致发光材料,以降低制备工艺的难度,提高OLED器件的性能,扩大OLED器件的应用范围,实属必要。
发明内容
鉴于以上所述现有技术的缺点,本发明的目的在于提供一种新型的、具有较高的溶解能力、较高的空穴迁移能力及较好的稳定性的有机电致发光材料,以降低制备工艺的难度,提高OLED器件的性能,扩大OLED器件的应用范围。
为实现上述目的,本发明提供一种有机电致发光材料,所述有机电致发光材料为不对称胺化合物,其结构通式包括如下中的一种:
其中,X为O或S;R1、R2、R3相同或不同,独立选自取代或未取代的环形成碳数为6~30的芳基、取代或未取代的环形成原子数为5~30的杂芳基、取代或未取代的碳数为1~30的烷基、取代或未取代的碳数为1~30的氟烷基、取代或未取代的环形成碳数为3~30的环烷基、取代或未取代的碳数为7~30的芳烷基、取代磷酰基、取代甲硅烷基、取代锗基、氰基、硝基或羧基。
可选的,R1、R2、R3独立选自以下基团中的任意一种:
可选地,所述有机电致发光材料选自如下化合物中的任意一种:
可选地,所述有机电致发光材料的溶解度大于10mg/ml。
本发明还提供上述有机电致发光材料在有机致电发光器件中的应用;所述有机电致发光材料在所述有机电致发光器件中用作空穴注入传输层。
本发明还提供一种有机电致发光器件,所述有机电致发光器件包括空穴注入传输层,且所述空穴注入传输层包含上述有机电致发光材料。
可选地,所述空穴注入传输层还包含P型材料,且在所述空穴注入传输层中,所述有机电致发光材料的质量百分比的范围包括80%~99.5%。
可选地,所述有机电致发光器件的电子传输层包含掺杂的金属,所述金属包括碱金属、碱土金属及稀土金属中的一种或组合。
可选地,所述有机电致发光器件包括顶发光器件及底发光器件中的一种或组合。
本发明还提供一种显示装置,所述显示装置包括上述所述有机电致发光器件。
本发明还提供一种电子设备,所述电子设备包括上述所述有机电致发光器件。
如上所述,本发明提供的包含二苯并呋喃或二苯并噻吩基团的不对称胺结构的有机电致发光材料,具有较高的溶解能力、较高的空穴迁移能力及较好的稳定性,可以被应用在有机电致发光领域,作为空穴注入传输材料使用,从而可降低制备工艺的难度,提高OLED器件的性能,扩大OLED器件的应用范围。
附图说明
图1显示为本发明中的底发光器件的结构示意图。
图2显示为本发明中的单空穴器件的结构示意图。
元件标号说明
101 阳极
102 空穴注入层
103 空穴传输层
104 电子阻挡层
105 发光层
106 空穴阻挡层
107 电子传输层
108 阴极
111 阳极
112 空穴注入传输复合层
113 阴极
具体实施方式
以下通过特定的具体实例说明本发明的实施方式,本领域技术人员可由本说明书所揭露的内容轻易地了解本发明的其他优点与功效。本发明还可以通过另外不同的具体实施方式加以实施或应用,本说明书中的各项细节也可以基于不同观点与应用,在没有背离本发明的精神下进行各种修饰或改变。
请参阅图1~图2。需要说明的是,本实施例中所提供的图示仅以示意方式说明本发明的基本构想,遂图式中仅显示与本发明中有关的组件而非按照实际实施时的组件数目、形状及尺寸绘制,其实际实施时各组件的型态、数量及比例可为一种随意的改变,且其组件布局型态也可能更为复杂。
本发明提供一种有机电致发光材料,所述有机电致发光材料为不对称胺化合物,其结构通式包括如下中的一种:
其中,X为O或S;R1、R2、R3相同或不同,独立选自取代或未取代的环形成碳数为6~30的芳基、取代或未取代的环形成原子数为5~30的杂芳基、取代或未取代的碳数为1~30的烷基、取代或未取代的碳数为1~30的氟烷基、取代或未取代的环形成碳数为3~30的环烷基、取代或未取代的碳数为7~30的芳烷基、取代磷酰基、取代甲硅烷基、取代锗基、氰基、硝基或羧基。
作为该实施例的进一步实施例,R1、R2、R3独立选自以下基团中的任意一种:
具体的,所述有机电致发光材料采用包含二苯并呋喃或者二苯并噻吩基团的不对称的胺的化合物,使得所述有机电致发光材料具有良好的空穴迁移能力、良好的溶剂溶解能力及较好的稳定性。其中,所述有机电致发光材料的溶解度的范围可大于10mg/ml。所述有机电致发光材料可以被应用在有机电致发光领域,作为空穴注入传输材料使用,从而可降低制备工艺的难度,提高OLED器件的性能,扩大OLED器件的应用范围。
作为该实施例的进一步实施例,所述有机电致发光材料可选自如下化合物中的任意一种:
具体的,以下提供本发明的几种化合物的具体合成实施例:
合成路线如下:
1)中间体HT1-3的合成
将化合物HT1-1(5525.2mg,10mmol)、化合物HT1-2(931.3mg,10mmol)、三(二亚苄基丙酮)二钯(183.1mg,0.2mmol)、三叔丁基膦(1ml,1N,1mmol)、叔丁基醇钠(1441.5mg,15mmol),加入到60ml甲苯中,在氮气保护下,90℃加热5h,反应液降至室温,过滤,减压浓缩有机液,粗品用硅胶柱纯化,得到中间体HT1-3(5010.0mg,收率88.72%)。其中,HPLC(HighPerformance Liquid Chromatography,高效液相色谱)纯度为96.10%,产物MS:[MW+1]=565.8,MS表示(Mass Spectrometry,MS质谱法),MW表示摩尔质量。
2)中间体HT1-5的合成
提供中间体HT1-3(4517.8mg,8mmol),化合物HT1-4(1907.6mg,8mmol),三(二亚苄基丙酮)二钯(146.5mg,0.16mmol),三叔丁基膦(0.8ml,1N,0.8mmol),叔丁基醇钠(1153.2mg,12mmol),加入到60ml甲苯中,在氮气保护下,80℃加热4h,反应液降至室温,过滤,减压浓缩有机液,粗品用硅胶柱纯化,得到中间体HT1-5(4125.0mg,收率76.36%)。其中,HPLC纯度为97.15%,产物MS:[MW+1]=676.2。
3)化合物HT1的合成
将中间体HT1-5(3376.3mg,5mmol),化合物HT1-6(1272mg,6mmol),四三苯基膦钯(289mg,0.25mmol),碳酸钾(2570mg,15mmol),水(10ml)加入到50ml四氢呋喃中,在氮气保护下,加热回流6h,反应液降至室温,过滤,减压浓缩有机液,粗品用硅胶柱纯化,得到化合物HT1(3022.2mg,收率74.90%)。其中,HPLC纯度98.36%,产物MS:[MW+1]=808.0,HNMR(CDCl3,400MHz):7.0-7.1(m,3H),7.2-7.6(m,31H)7.7-7.8(m,6H),8.02-8.06(m,2H),HNMR为核磁标准氢谱。
合成路线如下:
化合物HT2的合成
将中间体HT1-5(675.3mg,1mmol),化合物HT2-1(273.7mg,1.2mmol),四三苯基膦钯(115.6mg,0.1mmol),碳酸钾(414mg,3mmol),水(4ml)加入到20ml四氢呋喃中,在氮气保护下,加热回流6h。反应液降至室温,过滤,减压浓缩有机液,粗品用硅胶柱纯化,得到HT2(605.6mg,收率73.67%)。其中,中间体HT1-5的合成可参阅HT1的合成过程,此处不再赘述,但并不局限于此。HPLC纯度为97.90%,产物MS:[MW+1]=824.0,HNMR(CDCl3,400MHz):7.0-7.1(m,3H),7.2-7.6(m,31H)7.7-7.8(m,6H),8.02-8.06(m,2H)。
合成路线如下:
1)中间体HT3-3的合成
将化合物HT3-1(4941.8mg,20mmol),化合物HT3-2(4400mg,26mmol),三(二亚苄基丙酮)二钯(366mg,0.04mmol),三叔丁基膦(2ml,1N,2mmol),叔丁基醇钠(2883mg,30mmol)加入到100ml甲苯中,在氮气保护下,80℃加热6h。反应液降至室温,过滤,减压浓缩有机液,粗品用硅胶柱纯化,得到中间体HT3-3(5462,6mg,收率81.48%)。HPLC纯度为93.50%,产物MS:[MW+1]=336.4。
2)中间体HT3-5的合成
将中间体HT3-3(5031mg,15mmol),化合物HT3-4(5744mg,16mmol),三(二亚苄基丙酮)二钯(366mg,0.04mmol),三叔丁基膦(2ml,1N,2mmol),碳酸铯(9774mg,30mmol)加入到100ml甲苯中,在氮气保护下,80℃加热4h。反应液降至室温,过滤,减压浓缩有机液,粗品用硅胶柱纯化,得到中间体HT3-5(6234.0mg,收率73.36%)。HPLC纯度为95.28%,产物MS:[MW+1]=567.1。
3)中间体HT3-7的合成
将中间体HT3-5(3399mg,6mmol),化合物HT3-6(838.1mg,9mmol),三(二亚苄基丙酮)二钯(183.1mg,0.2mmol),三叔丁基膦(1ml,1N,1mmol),叔丁基醇钠(1729.8mg,18mmol)加入到60ml甲苯中,氮气保护下,90℃加热16h。反应液降至室温,过滤,减压浓缩有机液,粗品用硅胶柱纯化,得到中间体HT3-7(2448.5mg,收率70.50%)。HPLC纯度为92.60%,产物MS:[MW+1]=579.8。
4)化合物HT3合成:
将中间体HT3-7(1157.4mg,2mmol),化合物HT3-8(969.6mg,3mmol),三(二亚苄基丙酮)二钯(183.1mg,0.2mmol),三叔丁基膦(1ml,1N,1mmol),叔丁基醇钠(576.6mg,6mmol)加入到60ml甲苯中,在氮气保护下,120℃加热4h。反应液降至室温,过滤,减压浓缩有机液,粗品用硅胶柱纯化,得到化合物HT3(855.0mg,收率52.07%)。HPLC纯度为96.90%,产物MS:[MW+1]=822.0,HNMR(CDCl3,400MHz):6.92(d,1H),7.0-7.2(m,4H),7.3-7.6(m,27H),7.7-7.8(m,5H),7.95-8.02(m,3H)。
合成路线如下:
化合物HT4合成
将中间体HT3-7(1157.4mg,2mmol),化合物HT4-1(1017.8mg,3mmol),三(二亚苄基丙酮)二钯(183.1mg,0.2mmol),三叔丁基膦(1ml,1N,1mmol),叔丁基醇钠(576.6mg,6mmol)加入到60ml甲苯中,氮气保护下,120℃加热4h。反应液降至室温,过滤,减压浓缩有机液,粗品用硅胶柱纯化,得到HT4(844.5mg,收率50.47%)。其中,中间体HT3-7的合成参阅化合物HT3的合成过程,此处不再赘述,但并不局限于此。HPLC纯度为97.10%,产物MS:[MW+1]=838.0,HNMR(CDCl3,400MHz):6.92(d,1H),7.0-7.2(m,4H),7.3-7.6(m,27H),7.7-7.8(m,5H),7.95-8.02(m,3H)。
合成路线如下:
1)中间体HT5-3的合成
将化合物HT5-1(2036,7mg,10mmol),化合物HT5-2(7412.7mg,30mmol),三(二亚苄基丙酮)二钯(183.1mg,0.2mmol),三叔丁基膦(1ml,1N,1mmol),叔丁基醇钠(2883mg,30mmol)加入到100ml甲苯中,在氮气保护下,90℃加热5h。反应液降至室温,过滤,减压浓缩有机液,粗品用硅胶柱纯化,得到中间体HT5-3(3448.5mg,收率66.32%)。其中,HPLC纯度为95.08%,产物MS:[MW+1]=537.0。
2)中间体HT5-5的合成
将中间体HT5-3(3216.3mg,6mmol),化合物HT5-4(838.1mg,9mmol),三(二亚苄基丙酮)二钯(183.1mg,0.2mmol),三叔丁基膦(1ml,1N,1mmol),叔丁基醇钠(1729.8mg,18mmol)加入到60ml无水二氧六环中,在氮气保护下,90℃加热16h。反应液降至室温,过滤,减压浓缩有机液,粗品用硅胶柱纯化,得到中间体HT5-5(1668.5mg,收率46.90%)。HPLC纯度为94.40%,产物MS:[MW+1]=593.8。
3)化合物HT5的合成
将中间体HT5-5(1185.4mg,2mmol),化合物HT5-6(969.6mg,3mmol),三(二亚苄基丙酮)二钯(183.1mg,0.2mmol),三叔丁基膦(1ml,1N,1mmol),叔丁基醇钠(576.6mg,6mmol),加入到60ml无水二氧六环中,在氮气保护下,100℃加热16h。反应液降至室温,过滤,减压浓缩有机液,粗品用硅胶柱纯化,得到HT5(744.5mg,收率44.58%)。HPLC纯度为97.50%,MS:[MW+1]=836.0,HNMR(CDCl3,400MHz):6.9-7.0(m,2H),7.05-7.1(m,3H),7.2-7.4(m,14H),7.5-7.6(m,9H),7.7-7.8(m,4H),7.85-8.0(m,6H)。
合成路线如下:
化合物HT6的合成
将中间体HT5-5(592.7mg,1mmol),化合物HT6-1(508.5mg,1.5mmol),三(二亚苄基丙酮)二钯(91.5mg,0.1mmol),三叔丁基膦(1ml,1N,1mmol),叔丁基醇钠(288.3mg,3mmol)加入到40ml无水二氧六环中,在氮气保护下,100℃加热16h。反应液降至室温,过滤,减压浓缩有机液,粗品用硅胶柱纯化,得到化合物HT6(320.6mg,收率37.60%)。其中,中间体HT5-5的合成参阅HT6的合成过程,此处不再赘述,但并不局限于此。HPLC纯度为98.12%,产物MS:[MW+1]=852.0。HNMR(CDCl3,400MHz):6.9-7.0(m,2H),7.05-7.1(m,3H),7.2-7.4(m,14H),7.5-7.6(m,9H),7.7-7.8(m,4H),7.85-8.0(m,6H)。
合成路线如下:
1)中间体HT7-3的合成
将化合物HT7-1(5525.2mg,10mmol),化合物HT7-2(2030.8mg,12mmol),三(二亚苄基丙酮)二钯(183.1mg,0.2mmol),三叔丁基膦(1ml,1N,1mmol),叔丁基醇钠(1441.5mg,15mmol)加入到60ml甲苯中,在氮气保护下,90℃加热5h。反应液降至室温,过滤,减压浓缩有机液,粗品用硅胶柱纯化,得到中间体HT7-3(5225.2mg,收率81.28%)。HPLC纯度为96.52%,MS:[MW+1]=641.8。
2)化合物HT7的合成
将中间体HT7-3(3204.1mg,5mmol),化合物HT7-4(1615.9mg,5mmol),三(二亚苄基丙酮)二钯(91.6mg,0.1mmol),三叔丁基膦(0.5ml,1N,0.5mmol),叔丁基醇钠(961mg,10mmol)加入到40ml甲苯中,在氮气保护下,120℃加热6h。反应液降至室温,过滤,减压浓缩有机液,粗品用硅胶柱纯化,得到化合物HT7(2645mg,收率59.91%)。HPLC纯度为98.44%,产物MS:[MW+1]=884.0,HNMR(CDCl3,400MHz):7.3-7.5(m,18H),7.52-7.75(m,18H),7.8-7.9(m,8H),7.95-8.0(m,2H)。
合成路线如下:
化合物HT8的合成
将中间体HT7-3(1602.1mg,2.5mmol),化合物HT8-1(807.9mg,2.5mmol),三(二亚苄基丙酮)二钯(45.8mg,0.05mmol),三叔丁基膦(0.25ml,1N,0.25mmol),叔丁基醇钠(484mg,5mmol)加入到30ml甲苯中,在氮气保护下,120℃加热6h。反应液降至室温,过滤,减压浓缩有机液,粗品用硅胶柱纯化,得到化合物HT8(1418.2mg,收率63.10%)。HPLC纯度为96.80%,产物MS:[MW+1]=900.2,HNMR(CDCl3,400MHz):7.3-7.5(m,18H),7.52-7.75(m,18H),7.8-7.9(m,8H),7.95-8.0(m,2H)。
依据上述技术方案,只需要简单替换对应的原料,可以合成以下化合物:
作为该实施例的进一步实施例,所述有机电致发光材料可应用于有机致电发光(OLED)器件中,其中,所述有机电致发光材料在所述有机电致发光器件中优选为用作空穴注入传输层。
具体的,所述有机致电发光材料由于具有较高的溶解能力、较高的空穴迁移能力及较好的稳定性,因此可用以制作OLED器件的空穴注入传输层,以降低制备工艺的难度,提高OLED器件的性能,扩大OLED器件的应用范围,所述空穴注入传输层至少包括空穴传输层还可包括空穴注入层及电子阻挡层,本发明所述有机电致发光材料可应用于所述空穴传输层及所述空穴注入层中的一种或组合。
本发明还提供一种有机电致发光(OLED)器件,所述有机电致发光器件包括阳极、阴极及位于所述阳极与阴极之间的有机层,其中,所述有机层至少包括空穴注入传输层、发光层及电子注入传输层,所述空穴注入传输层包含所述有机电致发光材料。
具体的,所述空穴注入传输层至少包括空穴传输层还可包括空穴注入层及电子阻挡层,本发明所述有机电致发光材料可应用于所述空穴传输层及所述空穴注入层中的一种或组合。所述电子注入传输层至少包括电子传输层,还可包括电子注入层及空穴阻挡层中的一种或组合。
作为该实施例的进一步实施例,所述空穴注入传输层还包含P型材料,且在所述空穴注入传输层中,所述有机电致发光材料的质量百分比的范围包括80%~99.5%。
具体的,所述空穴注入传输层中的所述空穴传输层及空穴注入层中的一种或组合可仅应用所述有机电致发光材料;为进一步的提升所述有机电致发光材料的空穴注入传输性能,所述空穴传输层及空穴注入层中的一种或组合还可包括由所述有机电致发光材料与P型材料所形成的混合材料制成,且在所述混合材料中所述有机电致发光材料的质量百分比的范围可包括80%~99.5%,如85%,90%,95%。
作为该实施例的进一步实施例,所述有机电致发光器件的电子传输层包含掺杂的金属,所述金属包括碱金属、碱土金属及稀土金属中的一种或组合。
具体的,所述有机电致发光器件的所述电子传输层可包括由金属掺杂的材料制成,以进一步的提高所述电子传输层的电子传输性能,从而提高所述有机电致发光器件的性能。其中,所述金属可包括Yb金属、Li金属及Sm金属中的一种或组合。
作为该实施例的进一步实施例,所述阳极的材料可包括氧化铟锡、氧化锌、氧化锡锌、金、银或铜中的至少一种,所述阴极的材料可选自锂、镁、银、钙、锶、铝、铟、铜、金和银中的至少一种。
作为该实施例的进一步实施例,所述有机电致发光器件可包括顶发光器件及底发光器件中的一种或组合,当采用所述顶发光器件,所述有机电致发光器件优选包含与所述阴极相接触的光学耦合层。
作为该实施例的进一步实施例,所述有机电致发光器件包括单色器件及多色器件中的一种或组合。
作为该实施例的进一步实施例,所述有机电致发光器件可被应用于制备显示装置或电子设备。
具体的,可将上述任一所述有机电致发光材料应用于所述有机电致发光器件中的所述空穴注入传输层,以制备包括OLED显示面板的所述显示装置,所述电子设备可包括手机、电脑、电视机、智能穿戴、智能家居设备等,此处不作特殊限定。
如图1,所述有机电致发光器件采用底发光器件,所述底发光器件自下而上依次包括:阳极101,ITO(15nm)/空穴注入层102,HT1:PD-1(10nm,质量百分比如表1)/空穴传输层103,HT1(100nm)/电子阻挡层104,EBL(20nm)/发光层105,BH:BD(30nm,质量百分比97%:3%)/空穴阻挡层106,HBL(10nm)/电子传输层107,ET:LIQ(30nm,质量百分比50%:50%)/阴极108,Ag(100nm)。需要说明的是,表1中,实施例与对比例中器件的对应各层的制备方法及测试条件均相同。
表1:
由表1可以得出,本发明提供的包含二苯并呋喃或二苯并噻吩基团的不对称胺结构的有机电致发光材料所形成的OLED器件具有较低的电压及较高的光效率,可扩大OLED器件的应用范围。
为进一步说明所述有机电致发光材料的性能,本发明还提供一种单空穴器件,如图2,所述单空穴器件包括阳极111,ITO(厚度15nm)/空穴注入传输复合层112/阴极113,Ag(厚度100nm),其中,所述空穴注入传输复合层112依次包括:REF1:PD-1(厚度10nm,质量百分比95%:5%)/HT(X),(厚度及材料如表2)/PD-1(厚度10nm)。需要说明的是,表2中,实施例与对比例中器件的对应各层的制备方法及测试条件均相同,电压是在电流为10mA/cm2下测得:
表2:
具体的,在表2中,HT1~HT4、REF1、REF2的化合物的结构式如下:
由表2可以得出,所述单空穴器件具有较低的电压(HOD),且随着所述有机电致发光材料厚度的变化,所述电压变化较小,因此所述有机电致发光材料具有较好的空穴传输性能及稳定性,所述有机电致发光材料可以被应用在有机电致发光领域,作为空穴注入传输材料使用,从而可提高OLED器件的稳定性,扩大OLED器件的应用范围。
综上所述,本发明提供的包含二苯并呋喃或二苯并噻吩基团的不对称胺结构的有机电致发光材料,具有较高的溶解能力、较高的空穴迁移能力及较好的稳定性,可以被应用在有机电致发光领域,作为空穴注入传输材料使用,从而可提高OLED器件的性能,扩大OLED器件的应用范围。所以,本发明有效克服了现有技术中的种种缺点而具高度产业利用价值。
上述实施例仅例示性说明本发明的原理及其功效,而非用于限制本发明。任何熟悉此技术的人士皆可在不违背本发明的精神及范畴下,对上述实施例进行修饰或改变。因此,举凡所属技术领域中具有通常知识者在未脱离本发明所揭示的精神与技术思想下所完成的一切等效修饰或改变,仍应由本发明的权利要求所涵盖。
Claims (11)
4.根据权利要求1所述的有机电致发光材料,其特征在于:所述有机电致发光材料的溶解度大于10mg/ml。
5.一种权利要求1~4中任一项所述的有机电致发光材料在有机致电发光器件中的应用;所述有机电致发光材料在所述有机电致发光器件中用作空穴注入传输层。
6.一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空穴注入传输层,且所述空穴注入传输层包含权利要求1~4中任一所述有机电致发光材料。
7.根据权利要求6所述的有机电致发光器件,其特征在于:所述空穴注入传输层还包含P型材料,且在所述空穴注入传输层中,所述有机电致发光材料的质量百分比的范围包括80%~99.5%。
8.根据权利要求6所述的有机电致发光器件,其特征在于:所述有机电致发光器件的电子传输层包含掺杂的金属,所述金属包括碱金属、碱土金属及稀土金属中的一种或组合。
9.根据权利要求6所述的有机电致发光器件,其特征在于:所述有机电致发光器件包括顶发光器件及底发光器件中的一种或组合。
10.一种显示装置,其特征在于:所述显示装置包括权利要求6~9中任一所述有机电致发光器件。
11.一种电子设备,其特征在于:所述电子设备包括权利要求6~9中任一所述有机电致发光器件。
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