CN111187254B - 一种基于咔唑的有机电致磷光材料组成物及其应用 - Google Patents
一种基于咔唑的有机电致磷光材料组成物及其应用 Download PDFInfo
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- CN111187254B CN111187254B CN202010027859.7A CN202010027859A CN111187254B CN 111187254 B CN111187254 B CN 111187254B CN 202010027859 A CN202010027859 A CN 202010027859A CN 111187254 B CN111187254 B CN 111187254B
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 239000000463 material Substances 0.000 title claims abstract description 34
- 239000000203 mixture Substances 0.000 title claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 239000010410 layer Substances 0.000 claims description 133
- 238000002347 injection Methods 0.000 claims description 18
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- 230000005525 hole transport Effects 0.000 claims description 14
- 239000012044 organic layer Substances 0.000 claims description 12
- 239000002346 layers by function Substances 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 6
- 108091008695 photoreceptors Proteins 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 abstract description 3
- 238000002474 experimental method Methods 0.000 abstract description 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229940125758 compound 15 Drugs 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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- 238000004440 column chromatography Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- -1 dibenzofuranyl Chemical group 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 2
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- OHHKQBZOURGNLR-UHFFFAOYSA-N 4-bromo-2-chloro-1-iodobenzene Chemical compound ClC1=CC(Br)=CC=C1I OHHKQBZOURGNLR-UHFFFAOYSA-N 0.000 description 1
- IVDFJHOHABJVEH-UHFFFAOYSA-N HOCMe2CMe2OH Natural products CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明公开了有机电致发光材料相关技术领域,特别涉及一种基于咔唑的有机电致磷光材料组成物及其应用,包括具有以下结构式I的化合物:Ar表示为单键的C6‑C30的取代或者未取代的芳基,单键的C3‑C30的取代或者未取代的杂芳基;Cz表示为C6‑C30的取代或者未取代的咔唑基;实验表明,本发明如结构式I的基于咔唑的化合物,具有较好热稳定性,高发光效率,高发光纯度,可溶液加工;采用该基于咔唑的化合物制作的有机电致发光器件,具有电致发光效率良好和色纯度优异,以及寿命长的优点。
Description
技术领域
本发明涉及有机电致发光材料相关技术领域,特别涉及一种基于咔唑的有机电致磷光材料组成物及其应用。
背景技术
有机电致发光器件(OLEDs)为在两个金属电极之间通过旋涂或者真空蒸镀沉积一层有机材料制备而成的器件,一个经典的三层有机电致发光器件包括空穴传输层,发光层和电子传输层。由阳极产生的空穴经空穴传输层跟由阴极产生的电子经电子传输层结合在发光层形成激子,而后发光。有机电致发光器件可以根据需要通过改变发光层的材料来调节发射各种需要的光。
有机电致发光器件作为一种新型的显示技术,具有自发光、宽视角、低能耗、效率高、薄、色彩丰富、响应速度快、适用温度范围广、低驱动电压、可制作柔性可弯曲与透明的显示面板以及环境友好等独特优点,可以应用在平板显示器和新一代照明上,也可以作为LCD的背光源。
自从20世纪80年代底发明以来,有机电致发光器件已经在产业上有所应用,比如作为相机和手机等屏幕,但是目前的OLED器件由于效率低,使用寿命短等因素制约其更广泛的应用,特别是大屏幕显示器,因此需要提高器件的效率。而制约其中的一个重要因素就是有机电致发光器件中的有机电致发光材料的性能。另外由于OLED器件在施加电压运行的时候,会产生焦耳热,使得有机材料容易发生结晶,影响了器件的寿命和效率,因此,也需要开发稳定高效的有机电致发光材料。
有机电致磷光现象,突破了有机电致发光量子效率低于25%的理论限制,提升到100%(BaldoM.A.,ForrestS.R.Etal,Nature,1998,395,151-154),其应用也大大地提高了有机电致发光器件的效率。一般地,电致磷光需要采用主客体掺杂技术,常用的作为磷光主体材料的CBP(4,4'-bis(9-carbazolyl)-biphenyl)具有高效和高三线态能级,当其作为主体材料时,三线态能量能够有效地从发光主体材料转移到客体磷光发光材料。但是由于CBP的空穴易传输而电子难流动的特性,使得发光层的电荷不平衡,结果降低了器件的效率。
鉴于溶液旋涂沉积工艺在实现高分辨率,低成本和大面积的OLED显示器件同时,易于实现大规模生产,从而得到关注。为了满足市场的这些严格要求,开发具有较好热稳定性,高发光效率,高发光纯度的有机电致发光器件,是现有技术迫切需要解决的问题。
发明内容
针对现有技术存在的需要开发具有较好热稳定性,高发光效率,高发光纯度的有机电致发光器件的技术问题,本发明提供一种基于咔唑的有机电致磷光材料组成物及其应用。
为实现上述目的,本发明的技术方案为:
一种基于咔唑的有机电致磷光材料组成物,包括具有以下结构式I的化合物:
Ar表示为单键的C6-C30的取代或者未取代的芳基,单键的C3-C30的取代或者未取代的杂芳基;Cz表示为C6-C30的取代或者未取代的咔唑基。
优选的,所述的基于咔唑的有机电致磷光材料组成物,Ar独立地表示为苯基,联苯基,萘基,三并苯基,N-芳基(C6-C30)或者C1-C4的烷基取代的咔唑基,蒽基,菲基,芘基,苝基,荧蒽基,(9,9-二烷基)芴基,(9,9-二取代或者未取代的芳基)芴基,9,9-螺芴基,取代或者未取代的二苯并噻吩基,取代或者未取代的二苯并呋喃基。
优选的,所述的基于咔唑的有机电致磷光材料组成物,为下列结构式1-22的化合物:
一种上述任一项所述的基于咔唑的有机电致磷光材料组成物的应用,包括有机电致发光器件,所述有机电致发光器件包括依次电连接的阳极、有机层和阴极,所述有机层包括发光层,或者包括所述发光层与空穴注入层、空穴传输层、空穴阻挡层、电子注入层、电子传输层中的至少一个功能层的组合;所述发光层和所述功能层包括所述结构式I的化合物。
优选的,所述的基于咔唑的有机电致磷光材料组成物的应用,所述有机层为所述发光层,依次电连接的所述发光层和所述电子传输层,依次电连接的所述发光层、所述电子传输层和所述电子注入层,依次电连接的所述空穴传输层和所述发光层,依次电连接的所述空穴注入层、所述空穴传输层和所述发光层,依次电连接的所述空穴传输层、所述发光层和所述电子传输层,依次电连接的所述空穴注入层、所述空穴传输层、所述发光层和所述电子传输层,依次电连接的所述空穴注入层、所述空穴传输层、所述发光层、所述电子传输层和所述电子注入层,依次电连接的所述空穴传输层、所述发光层、所述空穴阻挡层、所述电子传输层和所述电子注入层,或者依次电连接的所述空穴注入层、所述空穴传输层、所述发光层、所述空穴阻挡层、所述电子传输层和所述电子注入层。
优选的,所述的基于咔唑的有机电致磷光材料组成物的应用,所述结构式I的合物所在的功能层为所述空穴传输层、所述空穴注入层中的至少一层。
优选的,所述的基于咔唑的有机电致磷光材料组成物的应用,所述结构式I的化合物包括两种或两种以上的具体分子结构。
优选的,所述的基于咔唑的有机电致磷光材料组成物的应用,所述结构式I的化合物的重量占所述发光层总重量的20-99.9%。
优选的,所述的基于咔唑的有机电致磷光材料组成物的应用,所述有机层的总厚度为1-1000nm。
优选的,所述的基于咔唑的有机电致磷光材料组成物的应用,应用领域为有机电致发光器件、有机太阳能电池、有机薄膜晶体管、有机光感受器中的一个或多个领域。
本发明具有如下优点:
1.实验表明,本发明如结构式I的基于咔唑的化合物,具有较好热稳定性,高发光效率,高发光纯度,可溶液加工;
2.采用该基于咔唑的化合物制作的有机电致发光器件,具有电致发光效率良好和色纯度优异,以及寿命长的优点。
附图说明
为了更清楚地说明本发明实施例或现有技术中的技术方案,下面将对实施例或现有技术描述中所需要使用的附图作简单地介绍,显而易见地,下面描述中的附图仅仅是本发明的一些实施例,对于本领域普通技术人员来讲,在不付出创造性劳动的前提下,还可以根据这些附图获得其他的附图。
图1为化合物15的氢核磁谱图;
图2为本发明的一种有机电致发光器件结构示意图;
图3为有机电致发光器件的电压和亮度关系图;
图4为有机电致发光器件的电流密度和电流效率关系图;
图5为有机电致发光器件的电流密度和功率效率图;
图6为有机电致发光器件的电流密度和外量子效率图;
图2中:110-玻璃基板;120-阳极;130-空穴注入层;140-空穴传输层;150-发光层;160-空穴阻挡层;170-电子传输层;180-电子注入层;190-阴极。
具体实施方式
下面结合附图对本发明的具体实施方式作进一步说明。在此需要说明的是,对于这些实施方式的说明用于帮助理解本发明,但并不构成对本发明的限定。此外,在以下说明中,省略了对公知结构、技术及操作的描述,以避免不必要地混淆本发明的概念。另外,下面所描述的本发明各个实施方式中所涉及的技术特征只要彼此之间未构成冲突就可以相互组合。
需要说明的是,在本发明的描述中,术语“上”、“下”等指示的方位或位置关系为基于附图2所示对本发明结构的说明,仅是为了便于描述本发明的简便,而不是指示或暗示所指的装置或元件必须具有特定的方位、以特定的方位构造和操作,因此不能理解为对本发明的限制。
另外,除非另有明确的规定和限定,术语“安装”、“连接”应做广义理解,例如,连接可以是固定连接,也可以是可拆卸连接,或一体地连接;可以是机械连接,也可以是电连接;可以是直接相连,也可以通过中间媒介间接相连,可以是两个结构内部的连通。对于本领域的普通技术人员而言,可以根据本发明的总体思路,联系本方案上下文具体情况理解上述术语在本发明中的具体含义。
为便于教导本领域技术人员实施本发明的技术方案,谨以化合物15为例,通过其具体合成过程,展示本发明中结构式I的化合物的合成方式,本领域技术人员可在不需要进行创造性劳动的基础上,结合本发明实施例的教导与现有技术和自身经验,自行实施,获取包括上述22种结构式的化合物在内的更多的实施方式。
实施例1:化合物15的合成
反应路径如下:
(一)、中间体1的合成
在烧瓶中,加入4-溴-2-氯碘苯(25g,79.4mmol),3-吡啶硼酸频哪醇酯(16.3g,79.4mmol),碳酸钾(22g,160mmol),四氢呋喃(300mL),水(100mL),四三苯基膦钯(1g),在氮气保护下加热回流10小时,冷却,用二氯甲烷萃取,干燥,浓缩,粗产品经柱层析纯化得到产物14.2g,产率67%。
1HNMR:(400MHz,CDCl3)δ8.66-8.63(m,2H),7.79-7.76(tt,1H),7.69(d,1H),7.53-7.47(dd,1H),7.40-7.36(dd,1H),7.22(d,1H)。
(二)、中间体2的合成
在烧瓶中,加入中间体1(3g,11.3mmol),2-苯并菲硼酸(3.1g,11.3mmol),碳酸钾(2.7g,20mmol),四氢呋喃(20mL),水(10mL),四三苯基膦钯(0.2g),在氮气保护下加热回流10小时,冷却,用二氯甲烷萃取,干燥,浓缩,粗产品经柱层析纯化得到产物3.7g,产率79%。
1HNMR:(400MHz,CDCl3)δ8.89(d,1H),8.79-8.75(m,3H),8.71-8.67(m,4H),7.97(d,1H),7.94-7.89(m,2H),7.82-7.80(dd,1H),7.73-7.69(m,4H),7.52(d,1H),7.45-7.42(dd,1H)。
(三)化合物15的合成
在烧瓶中,加入中间体2(2.5g,6mmol),9-苯基咔唑-3-硼酸(1.72g,6mmol),碳酸钾(1.3g,10mmol),四氢呋喃(20mL),水(10mL),醋酸钯(0.1g),X-Phos(0.2g),氮气保护下加热回流24小时,冷却,用二氯甲烷萃取,干燥,浓缩,粗产品经柱层析纯化得到产物2.6g,产率68%;产物的氢核磁谱图如图1所示。
1HNMR:(400MHz,CDCl3)δ8.92(d,1H),8.67-8.76(m,5H),8.58-8.59(d,1H),8.50-8.52(m,1H),8.13-8.15(m,2H),7.97-8.00(m,2H),7.88-7.91(m,1H),7.60-7.70(m,5H),7.40-7.53(m,6H),7.23-7.32(m,4H),7.14-7.18(m,2H)。
实施例1制备的化合物可以在有机电致发光器件、有机太阳能电池、有机薄膜晶体管、有机光感受器等诸多领域进行应用;本处实施例中谨以制备OLED为例进行说明。
诚如前文所述,有机电致发光器件包括依次电连接的阳极、有机层和阴极,有机层包括发光层,或者包括发光层与空穴注入层、空穴传输层、空穴阻挡层、电子注入层、电子传输层中的至少一个功能层的组合;发光层和功能层包括结构式I的化合物。并且,有机层的具体形式多种多样,可以是仅有发光层,也可以是依次电连接的发光层和电子传输层,依次电连接的发光层、电子传输层和电子注入层,依次电连接的空穴传输层和发光层,依次电连接的空穴注入层、空穴传输层和发光层,依次电连接的空穴传输层、发光层和电子传输层,依次电连接的空穴注入层、空穴传输层、发光层和电子传输层,依次电连接的空穴注入层、空穴传输层、发光层、电子传输层和电子注入层,依次电连接的空穴传输层、发光层、空穴阻挡层、电子传输层和电子注入层,或者依次电连接的空穴注入层、空穴传输层、发光层、空穴阻挡层、电子传输层和电子注入层;需要补充说明的是,更优选的情况下,这里所列举的电连接层,写在最前面的层连接的电路更接近正极,写在最后面的层的连接电路更接近负极。并且其中的结构式I的合物所在的层,可以设置在发光层,以及功能层中的空穴传输层、空穴注入层中的某一层或者多层中。而且,结构式I的化合物还能包括两种或两种以上的具体分子结构。如此结合,实施例数量庞大,为使申请文件简要,本发明中谨举一例以教导本领域技术人员实施本发明,本领域技术人员可在不需要进行创造性劳动的基础上,结合本发明实施例的教导与现有技术和自身经验,自行实施,获取更多的实施方式。
实施例2:有机电致发光器件的制备
如图2所示,首先,将透明导电ITO玻璃基板110(上面带有阳极120)(中国南玻集团股份有限公司)依次经:去离子水,乙醇,丙酮和去离子水洗净,再用氧等离子处理30秒。
然后,在ITO上旋涂35nm厚的PEDOT:PSS(聚乙撑二氧噻吩-聚(苯乙烯磺酸盐))作为空穴注入层130,150℃下干燥30min;
然后,在空穴注入层130上旋涂20nm厚的TFB(聚(9,9-二辛基芴-CO-N-(4-丁基苯基)二苯胺))为空穴传输层140,150℃下干燥30min;
然后,在空穴传输层140上旋涂20nm厚的发光层150,其中,实施例1合成的化合物15为主体发光材料,而以12%重量比的Ir(ppy)3acac作为磷光掺杂客体材料,90℃下干燥30min;具体实施时,结构式I的化合物的重量可以占发光层总重量的20-99.9%;
然后,在发光层150上蒸镀10nm厚的TmPyPB作为空穴阻挡层160;
然后,在空穴阻挡层160上蒸镀10nm厚的TPBi作为电子传输层170;
最后,在电子传输层170上蒸镀1nmLiF为电子注入层180和120nmAl作为器件阴极190。
具体实施时,有机层的总厚度可以在1-1000nm间任意设置,所制备的器件(结构示意图如图2所示)用PhotoResearchPR650光谱仪测得的在15mA/cm2的电流密度下的电流效率为16.2cd/A,功率效率为4.4lm/W,外量子效率为4.1%,CIE(x,y)为(0.34,0.62),具体如图3、4、5和6所示。
对比实施例
除了用CBP代替化合物15做主体材料制备有机电致发光器件以外,本实施例的有机电致发光器件的制备方法跟实施例2均相同。
所制备的有机电致发光器件用PhotoResearchPR650光谱仪测得的在15mA/cm2的电流密度下的电流效率为8.8cd/A,功率效率为1.7lm/W,外量子效率为2.2%,CIE(x,y)为(0.35,0.61),具体如图3、4、5和6所示。
经过对比,可以看出,本发明的化合物用于制备有机电致发光器件,具有优良的器件效率,可以作为具有优良性能的磷光主体材料;相比较以CBP制备的器件,具有更高的效率,亮度,具有高的稳定性,制备的有机电致发光器件具有高的效率和光纯度。
在制备有机电致发光器件的实施例2和对比实施例中使用的其他化合物的结构式如下:
以上结合附图对本发明的实施方式作了详细说明,但本发明不限于所描述的实施方式。对于本领域的技术人员而言,在不脱离本发明原理和精神的情况下,在没有做出创造性劳动前提下,对这些实施方式进行多种变化、修改、替换和变型,仍落入本发明的保护范围内。
Claims (8)
1.一种基于咔唑的有机电致磷光材料组成物,其特征在于:为下列结构式1-10的任意化合物:
2.一种如权利要求1所述的基于咔唑的有机电致磷光材料组成物的应用,其特征在于:用于有机电致发光器件,所述有机电致发光器件包括依次电连接的阳极、有机层和阴极,所述有机层包括发光层,或者包括所述发光层与空穴注入层、空穴传输层、空穴阻挡层、电子注入层、电子传输层中的至少一个功能层的组合;所述发光层和所述功能层包括权利要求1所述的化合物。
3.根据权利要求2所述的基于咔唑的有机电致磷光材料组成物的应用,其特征在于:所述有机层为所述发光层,依次电连接的所述发光层和所述电子传输层,依次电连接的所述发光层、所述电子传输层和所述电子注入层,依次电连接的所述空穴传输层和所述发光层,依次电连接的所述空穴注入层、所述空穴传输层和所述发光层,依次电连接的所述空穴传输层、所述发光层和所述电子传输层,依次电连接的所述空穴注入层、所述空穴传输层、所述发光层和所述电子传输层,依次电连接的所述空穴注入层、所述空穴传输层、所述发光层、所述电子传输层和所述电子注入层,依次电连接的所述空穴传输层、所述发光层、所述空穴阻挡层、所述电子传输层和所述电子注入层,或者依次电连接的所述空穴注入层、所述空穴传输层、所述发光层、所述空穴阻挡层、所述电子传输层和所述电子注入层。
4.根据权利要求2所述的基于咔唑的有机电致磷光材料组成物的应用,其特征在于:所述权利要求1的化合物所在的所述功能层为所述空穴传输层、所述空穴注入层中的至少一层。
5.根据权利要求2所述的基于咔唑的有机电致磷光材料组成物的应用,其特征在于:所述发光层和所述功能层包括权利要求1所述化合物的两种或两种以上。
6.根据权利要求5所述的基于咔唑的有机电致磷光材料组成物的应用,其特征在于:所述权利要求1的化合物的重量占所述发光层总重量的20-99.9%。
7.根据权利要求5所述的基于咔唑的有机电致磷光材料组成物的应用,其特征在于:所述有机层的总厚度为1-1000nm。
8.根据权利要求1所述的基于咔唑的有机电致磷光材料组成物的应用,其特征在于:应用领域为有机电致发光器件、有机太阳能电池、有机薄膜晶体管、有机光感受器中的一个或多个领域。。
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