CN113121367A - 一种有机电致发光化合物及其制备方法与应用 - Google Patents
一种有机电致发光化合物及其制备方法与应用 Download PDFInfo
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- CN113121367A CN113121367A CN202110357780.5A CN202110357780A CN113121367A CN 113121367 A CN113121367 A CN 113121367A CN 202110357780 A CN202110357780 A CN 202110357780A CN 113121367 A CN113121367 A CN 113121367A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000000376 reactant Substances 0.000 claims abstract description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims abstract description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 9
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims abstract description 9
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- 238000006243 chemical reaction Methods 0.000 claims description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 230000005525 hole transport Effects 0.000 claims description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 238000002347 injection Methods 0.000 claims description 15
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 10
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
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- 125000003003 spiro group Chemical group 0.000 claims description 4
- -1 tert-butylphenyl Chemical group 0.000 claims description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
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- 238000003756 stirring Methods 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
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- 125000005264 aryl amine group Chemical group 0.000 description 5
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- VUEGYUOUAAVYAS-JGGQBBKZSA-N (6ar,9s,10ar)-9-(dimethylsulfamoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CNC3=C1 VUEGYUOUAAVYAS-JGGQBBKZSA-N 0.000 description 4
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 4
- DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 4
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- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
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- 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
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- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 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
Description
技术领域
本发明涉及有机合成技术领域,更具体的说是涉及一种有机电致发光化合物及其制备方法与应用。
背景技术
信息时代的到来,现代人们的生活水平发生了日新月异的变化,对显示技术的要求也在不断的提高,现有技术中,OLED技术具有对比度高、柔性化、可视角广、响应速度快等优点。这使得OLED技术具有了良好的替代传统显示技术的潜力。
通常OLED发光器件为层叠结构,由空穴注入层、空穴传输层、发光层、电子传输层和电子注入层等结构依次层叠组成。空穴传输层(HTL)负责调节空穴的注入速度和注入量,空穴传输材料直接影响OLED的效率和寿命。现有技术中,空穴传输区域中常用的化合物包括酞菁铜(CuPc)、4,4’-双[N-(1-萘基)-N-苯基氨基]联苯(NPB)、N,N’-二苯基-N,N’-双(3-甲基苯基)-(1,1’-联苯基)-4,4’-二胺(TPD)、4,4’,4”-三(3-甲基苯基苯基氨基)三苯胺(MTDATA)等。
但是,使用这些材料的OLED在使量子效率和使用寿命方面存在问题。这是因为空穴传输材料通常具有低的最高已占据分子轨道(HOMO)值,在发光层中生成的激子扩散到空穴传输层界面或者空穴传输层侧,最终导致在发光层内界面的发光或者发光层内的电荷不均衡,从而在空穴传输层的界面上发光,使有机电致发光器件的色纯度及效率变低。
因此,如何提供一种发光效率高且寿命较好和低电压的空穴传输材料是本领域技术人员亟需解决的技术问题。
发明内容
有鉴于此,本发明提供了一种一种发光效率高且寿命较好和低电压的有机电致发光化合物及其制备方法与其在有机电致发光器件中的应用。
为了实现上述目的,本发明采用如下技术方案:
一种有机电致发光化合物,其结构如式I所示:
其中:
所述R1独立的选自取代或未取代的C1-C10的直链烷基,取代或未取代的C3-C10的环烷基和取代或未取代的C1-C10的支链烷基中的任意一种;优选为甲基,乙基,丙基,叔丁基;
所述R2或R3为所在苯环的任意位置,且R2或R3在其所在苯环上的取代数量为0~4;
所述R2-R3独立地选自氢、氘、取代或未取代的C1-C30烷基、取代或未取代的3-30元环烷基、取代或未取代的3-30元杂环烷基、取代或未取代的C6-C30芳基、取代或未取代的3-30元杂芳基、取代或未取代的3-30元杂芳基胺基、取代或未取代的C6~C60芳基胺基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C60芳氧基中的一种或几种,且至少一个碳原子置换为杂原子氮、氧、硫或硅;
上述取代基能够与相邻取代基连接形成单环或多环C3-C30脂肪族环或3到30元芳香族环;
所述X为化学键、O、S、Si(R4R5)、C(R6R7)或NR8中的任意一种;
所述Ar1-Ar2独立地选自取代或未取代的C6-C30芳基、取代或未取代的3-30元杂芳基、取代或未取代的C10-C30稠环基、取代或未取代的C10-C30螺环基中的任意一种,且至少一个碳原子置换为杂原子氮、氧、硫或硅;
上述取代基能够与相邻取代基连接形成单环或C3-C30脂肪族环或C6-C30芳香族环;
所述L选自取代或未取代的C6-C30芳基或取代或未取代的3-30元杂芳基,优选为萘基、联苯基、菲基、苯基、芴基、芳胺基取代的芳基;
有益效果:本发明选择上述取代基得到的材料易于产品合成,且产品性能好。
优选的,R4-R8独立的选自取代或未取代的(C1-C30)烷基、取代或未取代的(3元-30元)环烷基、取代或未取代的(3元-30元)杂环烷基、取代或未取代的(C6-C30)芳基、取代或未取代的(3元-30元)杂芳基、取代或未取代的(3到30元)杂芳基胺基、取代或未取代的(C6~C60)芳基胺基、取代或未取代的(C1-C30)烷氧基,或与相邻取代基连接形成单环或多环(C3-C30)脂肪族环或(3元到30元)芳香族环中的一种或几种,且至少一个碳原子置换为杂原子氮、氧、硫或硅。
优选的,Ar1-Ar2独立地选自萘基、菲基、苯并菲,苯基、咔唑基、叔丁基苯基、甲基苯基、三联苯基、联苯基、芴基或螺基中的一种或几种。
在上述技术方案中,术语“经取代或未经取代的”意指被选自以下的一个、两个或更多个取代基取代:氘;卤素基团;腈基;羟基;羰基;酯基;甲硅烷基;硼基;经取代或未经取代的烷基;经取代或未经取代的环烷基;经取代或未经取代的烷氧基;经取代或未经取代的烯基;经取代或未经取代的烷基胺基;经取代或未经取代的杂环基胺基;经取代或未经取代的芳基胺基;经取代或未经取代的芳基;和经取代或未经取代的杂环基,或者被以上所示的取代基中的两个或更多个取代基相连接的取代基取代,或者不具有取代基。例如,“两个或更多个取代基相连接的取代基”可以包括联苯基。换言之,联苯基可以为芳基,或者可以解释为两个苯基相连接的取代基。
优选地,所述有机电致发光化合物包括下述结构中的任意一个:
一种有机电致发光化合物的制备方法,式I的合成反应路线如下:
具体制备方法包括以下步骤:
(1)将反应物A和反应物B依次溶于甲苯中,然后在惰性气体保护下一次加入Pd2(dba)3、P(t-Bu)3和t-BuONa,并升温至105-115℃,搅拌反应6-10h,再趁热抽滤后冷却、洗涤,将洗涤液分液并保留有机相,且将水相利用乙酸乙酯萃取,然后合并有机相与乙酸乙酯萃取相、干燥,并旋转蒸发去除溶剂后纯化,得到中间体C;
(2)在惰性气体保护下将所述中间体C、反应物D、四(三苯基膦)钯和碳酸钾依次加入至甲苯、乙醇、水的混合溶剂中,升温至95-105℃回流反应6-8h,反应结束后,冷却至室温析出固体、抽滤、水洗后醇洗,得到滤饼,再对滤饼干燥后重结晶,得到式I所示的化合物。
优选的,步骤(1)所述反应物A、反应物B、Pd2(dba)3、P(t-Bu)3和t-BuONa的摩尔比1:(1.1-1.4):(0.01-0.02):(0.05-0.06):(2.5-3.0)。
有益效果:在本发明限定的比例下反应得到的产物副产品少,速度快,容易提纯。
优选的,步骤(1)所述抽滤为利用硅藻土抽滤,以除去盐和催化剂;所述干燥为硫酸镁干燥;所述纯化为管柱色谱法纯化,且洗脱剂为二氯甲烷和石油醚;所述二氯甲烷和石油醚体积比为1:(1-9)。
有益效果:在本发明限定的洗脱剂比例下,能够将杂质点与产物分开,获得纯度很高的物质。
优选的,步骤(2)所述中间体C、反应物D、四(三苯基膦)钯和碳酸钾的摩尔比为1:(1.0-1.4):(0.01-0.03):(2.0-2.8)。
有益效果:在本发明限定的比例下反应得到的产物副产品少,速度快,容易提纯。
优选的,步骤(2)所述重结晶为将干燥后滤饼置于1,4-二氧六环中重结晶。
一种有机电致发光器件,包括第一电极、第二电极和置于所述两电极之间的有机化合物层,其特征在于,所述有机化合物层包括空穴传输层,所述空穴传输层包括权利要求1-3任一所述的有机电致发光化合物。
所述空穴传输材料是能够接收来自阳极或空穴注入层的空穴并将空穴传输至发光层的材料,并且具有高空穴迁移率的材料。
优选的,还包括空穴注入层、发光辅助层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层的中的一层或多层。
有益效果:本发明将式I所示化合物应用于有机电致发光器件中能够有效提高有机电致发光器件的发光效率,同时能够延长器件寿命。
优选的,所述第一电极作为阳极,阳极优选包含具有高逸出功的材料。例如氧化锡铟(ITO)或氧化铟锌(IZO)。由于在水和/或空气存在下本发明器件的寿命会缩短,所以所述器件被适当地(取决于应用)结构化、提供接点并最后密封。
所述电子阻挡层可以设置在空穴传输层与发光层之间。作为电子阻挡层,可以使用本领域中已知的材料,例如基于芳基胺的有机材料。
发光层的材料是一种通过分别接收来自空穴传输层和电子传输层的空穴和电子,并将所接收的空穴和电子结合而能发出可见光的材料。
发光层包含主体材料和掺杂材料;
主体材料和掺杂材料的质量比为90-99.5:0.5-10;
主体材料包含荧光主体和磷光主体;
掺杂材料包括荧光掺杂和磷光掺杂;
空穴阻挡层材料,可以使用现有技术中公知的具有空穴阻挡作用的化合物,例如,浴铜灵(BCP)等菲咯啉衍生物、噁唑衍生物、三唑衍生物、三嗪衍生物等,但不限于此。
电子传输层可以起到促进电子传输的作用。可以使用现有技术中公知的具有电子传输作用的化合物,例如,8-羟基喹啉的Al配合物;包含Alq3的配合物;有机自由基化合物;羟基黄酮-金属配合物等。
电子注入层可以起到促进电子注入的作用。具有传输电子的能力,防止发光层中产生的激子迁移至空穴注入层。本发明中使用的电子注入材料包括芴酮、蒽醌二甲烷、联苯醌、噻喃二氧化物、唑、二唑、三唑、咪唑、苝四羧酸、亚芴基甲烷、蒽酮等及其衍生物,金属配合物,含氮五元环衍生物等,但不限于此。
第二电极作为阴极,通常优选具有小功函数的材料使得电子顺利注入有机材料层。例如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅,或其合金。
经由上述的技术方案可知,与现有技术相比,本发明公开提供了一种有机电致发光化合物及其制备方法与应用,本发明以芳环及其衍生物为母核,引入芳胺侧链基团,由于芳胺侧链是优异的给电子基团,具有良好的空穴传输特性,即较高的空穴迁移率。使用该有机电致发光化合物制备的有机电致发光器件具有较高的发光效率;同时用芴基,芳基等取代基对母核进行性能调控,使得化合物具有低驱动电压、较长的寿命。
具体实施方式
下面将结合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:
一种有机电致发光化合物,其结构为化合物1所示,其合成路线如下:
化合物1的具体制备方法包括以下步骤:
步骤1:
在反应容器中加入化学式反应物A-1(50mmol)和反应物B-1(70mmol)溶于200ml甲苯之后,在氮气氛围下加入Pd2(dba)3(0.50mmol)、P(t-Bu)3(2.5mmol)、t-BuONa(125mmol)。添加后,使反应温度缓慢升温到105℃,并且搅拌混合物10h。使用硅藻土趁热抽滤,除去盐和催化剂,滤液冷却至室温后,接着将蒸馏水添加到滤液中进行洗涤,分液后保留有机相,用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层,并且使用旋转式蒸发器去除溶剂。以二氯甲烷:石油醚体积比为1:(1-9)作为洗脱剂,用管柱色谱法纯化剩余物质,获得中间体C-1(19.5g,Ms:481.52,产率为81%)。
步骤2:
N2保护下,将中间体C-41(35mmol)、反应物D-41(35mmol)、四(三苯基膦)钯(1.05mmol)和碳酸钾(98mmol)依次加入到150mL甲苯、50mL乙醇、50mL水的混合溶剂中,升温至95℃回流反应6h,反应结束后,冷却至室温,待固体析出完毕后,抽滤后用水洗涤除去盐,再用少量乙醇淋洗,干燥滤饼。置于1,4-二氧六环中重结晶(150mL),得到化合物1(19.1g,85%)。
对所得化合物1进行检测分析,结果如下:
质谱测试:理论值为643.87;测试值为643.54。
元素分析:
理论值为:C,91.41;H,6.42;N,2.18
测试值为:C,91.42;H,6.42;N,2.18
实施例2:
一种有机电致发光化合物,其结构为化合物26所示,其合成路线如下:
化合物26的具体制备方法包括以下步骤:
在反应容器中加入化学式反应物A-26(50mmol)和反应物B-26(60mmol)溶于200ml甲苯之后,在氮气氛围下加入Pd2(dba)3(1.0mmol)、P(t-Bu)3(3.0mmol)、t-BuONa(150mmol)。添加后,使反应温度缓慢升温到115℃,并且搅拌混合物6h。使用硅藻土趁热抽滤,除去盐和催化剂,滤液冷却至室温后,接着将蒸馏水添加到滤液中进行洗涤,分液后保留有机相,用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层,并且使用旋转式蒸发器去除溶剂。以二氯甲烷:石油醚体积比为1:(1-9)作为洗脱剂,用管柱色谱法纯化剩余物质,获得中间体C-26(24.1g,Ms:581.42,产率为83%)。
步骤2:
N2保护下,将中间体C-26(35mmol)、反应物D-26(49mmol)、四(三苯基膦)钯(0.70mmol)和碳酸钾(70mmol)分别加入到150mL甲苯、50mL乙醇、50mL水的混合溶剂中,升温至105℃回流反应7h,反应结束后,冷却至室温,待固体析出完毕后,抽滤后用水洗涤除去盐,再用少量乙醇淋洗,干燥滤饼。置于1,4-二氧六环中重结晶(150mL),得到化合物26(20.0g,80%)。
对所得化合物26进行检测分析,结果如下:
质谱测试:理论值为715.94;测试值为715.42。
元素分析:
理论值为:C,92.27;H,5.77;N,1.96
测试值为:C,92.26;H,5.77;N,1.97
实施例3:
一种有机电致发光化合物,其结构为化合物71所示,其合成路线如下:
化合物71的具体制备方法包括以下步骤:
步骤1:
在反应容器中加入化学式反应物A-71(50mmol)和反应物B-71(55mmol)溶于200ml甲苯之后,在氮气氛围下加入Pd2(dba)3(0.56mmol)、P(t-Bu)3(2.8mmol)、t-BuONa(150mmol)。添加后,使反应温度缓慢升温到110℃,并且搅拌混合物9h。使用硅藻土趁热抽滤,除去盐和催化剂,滤液冷却至室温后,接着将蒸馏水添加到滤液中进行洗涤,分液后保留有机相,用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层,并且使用旋转式蒸发器去除溶剂。以二氯甲烷:石油醚体积比为1:(1-9)作为洗脱剂,用管柱色谱法纯化剩余物质,获得中间体C-71(17.8g,Ms:455.34,产率为78%)。
步骤2:
N2保护下,将中间体C-71(35mmol)、反应物D-71(38.5mmol)、四(三苯基膦)钯(0.35mmol)和碳酸钾(84mmol)分别加入到150mL甲苯、50mL乙醇、50mL水的混合溶剂中,升温至100℃回流反应8h,反应结束后,冷却至室温,待固体析出完毕后,抽滤后用水洗涤除去盐,再用少量乙醇淋洗,干燥滤饼。置于1,4-二氧六环中重结晶(150mL),得到化合物71(17.4g,82%)。
对所得化合物71进行检测分析,结果如下:
质谱测试:理论值为605.78;测试值为605.56。
元素分析:
理论值为:C,89.22;H,5.82;N,2.31;O,2.64
测试值为:C,89.20;H,5.82;N,2.32;O,2.64
实施例4:
一种有机电致发光化合物,其结构为化合物84所示,其合成路线如下:
化合物84的具体制备方法包括以下步骤:
步骤1:
在反应容器中加入化学式反应物A-84(50mmol)和反应物B-84(55mmol)溶于200ml甲苯之后,在氮气氛围下加入Pd2(dba)3(0.56mmol)、P(t-Bu)3(2.8mmol)、t-BuONa(150mmol)。添加后,使反应温度缓慢升温到110℃,并且搅拌混合物10h。使用硅藻土趁热抽滤,除去盐和催化剂,滤液冷却至室温后,接着将蒸馏水添加到滤液中进行洗涤,分液后保留有机相,用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层,并且使用旋转式蒸发器去除溶剂。以二氯甲烷:石油醚体积比为1:(1-9)作为洗脱剂,用管柱色谱法纯化剩余物质,获得中间体C-84(18.9g,Ms:456.20,产率为83%)。
步骤2:
N2保护下,将中间体C-84(35mmol)、反应物D-84(38.5mmol)、四(三苯基膦)钯(0.35mmol)和碳酸钾(84mmol)分别加入到150mL甲苯、50mL乙醇、50mL水的混合溶剂中,升温至100℃回流反应8h,反应结束后,冷却至室温,待固体析出完毕后,抽滤后用水洗涤除去盐,再用少量乙醇淋洗,干燥滤饼。置于1,4-二氧六环中重结晶(150mL),得到化合物84(19.3g,81%)。
对所得化合物84进行检测分析,结果如下:
质谱测试:理论值为681.88;测试值为681.74。
元素分析:
理论值为:C,88.07;H,5.77;N,6.16
测试值为:C,88.05;H,5.78;N,6.17
实施例5-实施例24
参照实施例1的合成方法完成对化合物5,9,11,14,18,24,30,34,38,42,48,52,58,64,68,72,74,77,78,86的合成,质谱和分子式列于下表1。
另外,需要说明,本申请其他化合物参照上述所列举的实施例的合成方法均可获得。
表1:
应用例1
红光有机电致发光器件的制备
透明基板层为透明PI膜,对ITO阳极层(膜厚为150nm)进行洗涤,依次进行碱洗涤、纯水洗涤、干燥,再进行紫外线-臭氧洗涤以清除透明ITO表面的有机残留物。在进行了上述洗涤之后的ITO阳极层上,利用真空蒸镀装置,蒸镀膜厚为10nm的HAT-CN作为空穴注入层使用。接着蒸镀60nm厚度的化合物1作为空穴传输层。上述空穴传输材料蒸镀结束后,制作OLED发光器件的发光层,其结构包括OLED发光层所使用CBP作为主体材料(比例为95wt%),(btmp)2(acac)作为掺杂材料,掺杂比例为5wt%,发光层膜厚为40nm。
在上述发光层上真空蒸镀厚度为10nmTPBi作为空穴阻挡层,BAlq作为电子传输层;在上述电子传输层上真空蒸镀厚度为1.0nm羟基喹啉锂(Liq),作为电子注入层;在电子注入层上,制作膜厚为150nm的Al电极层,此层为阴极层使用。得到有机电致发光器件1.
器件结构如下:
ITO/HAT-CN/化合物1/CBP:(btmp)2(acac)/TPBi/BAlq/Liq/Al。
如上所述地完成OLED发光器件后,用公知的驱动电路将阳极和阴极连接起来,测量器件的电流效率以及器件的寿命。按照上述步骤完成电致发光器件的制作后,测量器件的驱动电压,发光效率和寿命。
相关材料的分子结构式如下所示:
应用例2-27
参照应用例1的方法将应用例1中使用的化合物1分别替换为化合物2,4,7,12,16,20,23,25,28,31,33,36,40,44,46,50,53,55,60,63,66,70,75,80,82,83,88作为空穴传输层,制备得到相应的有机电致发光器件2-27。
对比例1
按照与应用例1相同的制备方法制备有机电致发光器件,其中,空穴传输层的化合物替换为式A所示结构的化合物;
对比例2
按照与应用例1相同的制备方法制备有机电致发光器件,其中,空穴传输层的化合物替换为对比例2所示结构的化合物;
对应用例1-27以及对比例1~2制备的有机电致发光器件分别加以正向直流偏置电压,利用Photo Research公司的PR-650光度测量设备测定有机电致发光特性,亮度为8000cd/m2下利用McScience公司的寿命测定装置测定了T95的寿命。结果见表2。
表2应用例1-27以及对比例1~2制备的有机电致发光器件的发光特性测试结果(亮度值为8000cd/m2)
从表2可以看出,与传统的空穴传输材料相比(对比例1),驱动电压,发光效率,器件寿命都得到了显著提升。
与结构相似的空穴传输材料(对比例2)相比,本发明与对比例2都含有芴基,并且在芴基的9位存在取代基,存在芳胺侧链。
区别在于芳胺取代基的位置不同,本发明在芴基的9位存在芳胺基团和烷基,对比例芳胺基团在芴基的苯环上,且9位存在苯基取代。
在性能上驱动电压下降在0.8~1.5V左右,发光效率提升7.9%~13.8%,器件寿命提高51~90h,玻璃化转变温度提高6-18℃。
推测产生这种效果的原因在于芳胺基团取代位置的不同,使材料的空间结构跟有利于空穴传输,同时在9位引入烷基修饰,提高玻璃化转变温度。
由上述表2的结果能确认使用本发明提供的化合物作为空穴传输层材料制备的有机电致发光器件可以表现出高的发光效率及长寿命并降低驱动电压。
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。
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)
1.一种有机电致发光化合物,其特征在于,其结构如式I所示:
其中:
所述R1选自取代或未取代的C1-C10的直链烷基、取代或未取代的C3-C10的环烷基和取代或未取代的C1-C10的支链烷基中的任意一种;
所述R2或R3为所在苯环的任意位置,且所述R2和R3独立地选自氢、氘、取代或未取代的C1-C30烷基、取代或未取代的3-30元环烷基、取代或未取代的3-30元杂环烷基、取代或未取代的C6-C30芳基、取代或未取代的3-30元杂芳基、取代或未取代的3-30元杂芳基胺基、取代或未取代的C6~C60芳基胺基、取代或未取代的C1-C30烷氧基或取代或未取代的C6-C60芳氧基中的一种或几种,且其中至少一个碳原子置换为杂原子氮、氧、硫或硅;
所述X为化学键、O、S、Si(R4R5)、C(R6R7)或NR8中的任意一种;
所述Ar1和Ar2独立地选自取代或未取代的C6-C30芳基、取代或未取代的3-30元杂芳基、取代或未取代的C10-C30稠环基或取代或未取代的C10-C30螺环基中的任意一种,且其中至少一个碳原子置换为杂原子氮、氧、硫或硅;
所述L选自取代或未取代的C6-C30芳基或取代或未取代的3-30元杂芳基。
2.根据权利要求1所述的一种有机电致发光化合物,其特征在于,R4-R8独立的选自取代或未取代的C1-C30烷基、取代或未取代的3元-30元环烷基、取代或未取代的3-30元杂环烷基、取代或未取代的C6-C30芳基、取代或未取代的3-30元杂芳基、取代或未取代的3-30元杂芳基胺基、取代或未取代的C6~C60芳基胺基、取代或未取代的C1-C30烷氧基和与相邻取代基连接形成单环或多环C3-C30脂肪族环或3-30元芳香族环中的一种或几种,且至少一个碳原子置换为杂原子氮、氧、硫或硅。
3.根据权利要求1所述的一种有机电致发光化合物,其特征在于,Ar1-Ar2独立地选自萘基、菲基、苯并菲,苯基、咔唑基、叔丁基苯基、甲基苯基、三联苯基、联苯基、芴基和螺基中的一种或几种。
4.根据权利要求1所述的一种有机电致发光化合物的制备方法,其特征在于,式I的合成反应路线如下:
具体制备方法包括以下步骤:
(1)将反应物A和反应物B依次溶于甲苯中,然后在惰性气体保护下一次加入Pd2(dba)3、P(t-Bu)3和t-BuONa,并升温至105-115℃,搅拌反应6-10h,再趁热抽滤后冷却、洗涤,将洗涤液分液,保留有机相,且水相用乙酸乙酯萃取,然后合并所述有机相与乙酸乙酯萃取相、干燥,并旋转蒸发去除溶剂后纯化,得到中间体C;
(2)在惰性气体保护下将所述中间体C、反应物D、四(三苯基膦)钯和碳酸钾依次加入至甲苯、乙醇和水的混合溶剂中,升温至95-105℃回流反应6-8h,反应结束后,冷却至室温析出固体、抽滤、水洗后醇洗,得到滤饼,再对滤饼干燥后重结晶,得到式I所示的化合物。
5.根据权利要求4所述的一种有机电致发光化合物的制备方法,其特征在于,步骤(1)所述反应物A、反应物B、Pd2(dba)3、P(t-Bu)3和t-BuONa的摩尔比1:(1.1-1.4):(0.01-0.02):(0.05-0.06):(2.5-3.0)。
6.根据权利要求5所述的一种有机电致发光化合物的制备方法,其特征在于,步骤(1)所述干燥为硫酸镁干燥;所述纯化为管柱色谱法纯化,且洗脱剂为二氯甲烷和石油醚;所述二氯甲烷和石油醚体积比为1:(1-9)。
7.根据权利要求4所述的一种有机电致发光化合物的制备方法,其特征在于,步骤(2)所述中间体C、反应物D、四(三苯基膦)钯和碳酸钾的摩尔比为1:(1.0-1.4):(0.01-0.03):(2.0-2.8)。
8.根据权利要求7所述的一种有机电致发光化合物的制备方法,其特征在于,步骤(2)所述重结晶为将干燥后滤饼置于1,4-二氧六环中重结晶。
9.一种有机电致发光器件,包括第一电极、第二电极和置于所述两电极之间的有机化合物层,其特征在于,所述有机化合物层包括空穴传输层,所述空穴传输层包括权利要求1-3任一所述的有机电致发光化合物。
10.根据权利要求9所述的一种有机电致发光器件,其特征在于,还包括空穴注入层、发光辅助层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层的中的一层或多层。
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