CN108299389A - 一种基于菲和咔唑的化合物及其用途和有机电致发光器件 - Google Patents
一种基于菲和咔唑的化合物及其用途和有机电致发光器件 Download PDFInfo
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- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical class OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
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Abstract
本发明提供了一种基于菲和咔唑的化合物,其具有如下结构式:该化合物具有较好的热稳定性、高发光效率和高发光纯度,可以应用于有机电致发光器件、有机太阳能电池、有机薄膜晶体管或有机光感受器领域。本发明还提供了一种有机电致发光器件,该器件包含阳极、阴极和有机层,有机层包含发光层、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层,有机层中至少有一层含有如结构式I的化合物,采用该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领域,具体涉及一种基于菲和咔唑的化合物及其用途,还涉及一种有机电致发光器件。
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含空穴传输层、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%(Baldo M.A.,Forrest S.R.Et al,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。
发明内容
本发明提供了一种基于菲和咔唑的化合物,为具有如下结构式I的化合物:
其中,Ar1选自取代或者未取代的C6-C30的芳基;
Ar2选自取代或者未取代的C3-C30的杂芳基、取代或者未取代的C3-C30的芳膦基;
R1-R8独立地选自氢、氘、C1-C12的烷基、C1-C8的烷氧基、取代或者未取代的C6-C30的芳基。
可选的,Ar1选自苯基、氰基苯基、氟取代苯基、联苯基、二苯基取代苯基、萘基、三并苯基、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。
可选的,Ar2选自吡啶基、嘧啶基、哒嗪基、三嗪基、咪唑基、噁唑基、噻唑基、噻二唑基、喹啉基、异喹啉基、喹唑啉基、喹喔啉基、氮杂二苯并呋喃基、氮杂二苯并噻吩基、咪唑基,以上芳基和杂芳基还可以进一步为C1-C12的烷基取代。
可选的,R1-R8独立地选自氢、苯基、甲基。
进一步可选的,基于菲和咔唑的化合物为下列结构式1-68的化合物:
本发明的一种基于菲和咔唑的化合物可以应用在有机电致发光器件、有机太阳能电池、有机薄膜晶体管或有机光感受器领域。
本发明还提供了一种有机电致发光器件,该器件包含阳极、阴极和有机层,有机层包含发光层、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层;
可选的,有机层为发光层;
或者有机层为发光层和电子传输层;
或者有机层为发光层、电子传输层和电子注入层;
或者有机层为空穴传输层和发光层;
或者有机层为空穴注入层、空穴传输层和发光层;
或者有机层为空穴传输层、发光层和电子传输层;
或者有机层为空穴注入层、空穴传输层、发光层和电子传输层;
或者有机层为空穴注入层、空穴传输层、发光层、电子传输层和电子注入层;
或者有机层为空穴注入层、空穴传输层、阻挡层、发光层、电子传输层和电子注入层;
或者有机层为空穴传输层、发光层、电子传输层、电子注入层和空穴阻挡层;
或者有机层为空穴传输层、发光层、电子注入层和空穴阻挡层。
可选的,所述有机层中至少有一层含有如结构式I所述的基于菲和咔唑的化合物;
可选地,如结构式I所述的基于菲和咔唑的化合物所在的层为发光层、空穴传输层、空穴注入层。
可选的,如结构式I所述的基于菲和咔唑的化合物用于发光器件制备时,可以单独使用,也可以和其它化合物混合使用;如结构式I所述的基于菲和咔唑的化合物可以单独使用其中的一种化合物,也可以同时使用结构式I中的两种以上的化合物。
本发明的有机电致发光器件有机层的总厚度为1-1000nm,优选50-500nm。
本发明的有机电致发光器件在使用本发明具有结构式I的化合物时,可以搭配使用其它材料,如在空穴注入层、空穴传输层、发光层、电子传输层、电子注入层和阻挡层中等,而获得蓝光、绿光、黄光、红光或者白光。
本发明有机电致发光器件的空穴传输层和空穴注入层,所需材料具有很好的空穴传输性能,能够有效地把空穴从阳极传输到发光层上。除了可以使用具有本发明的化合物外,还可以包括其它小分子和高分子有机化合物,包括但不限于咔唑类化合物、三芳香胺化合物、联苯二胺化合物、芴类化合物、酞菁类化合物、六氰基六杂三苯(hexanitrilehexaazatriphenylene)、2,3,5,6-四氟-7,7',8,8'-四氰二甲基对苯醌(F4-TCNQ)、聚乙烯基咔唑、聚噻吩、聚乙烯或聚苯磺酸。
本发明的有机电致发光器件的发光层,具有很好的发光特性,可以根据需要调节可见光的范围。除本发明的具有结构式I化合物外,还可以含有如下化合物,但是不限于此,萘类化合物、芘类化合物、芴类化合物、菲类化合物、类化合物、荧蒽类化合物、蒽类化合物、并五苯类化合物、苝类化合物、二芳乙烯类化合物、三苯胺乙烯类化合物、胺类化合物、苯并咪唑类化合物、呋喃类化合物、有机金属螯合物。
本发明有机电致发光器件的有机电子传输材料要求具有很好的电子传输性能,能够有效地把电子从阴极传输到发光层中,具有很大的电子迁移率。可以选择如下化合物,但是不限于此:氧杂恶唑、噻唑类化合物、三氮唑类化合物、三氮嗪类化合物、三氮杂苯类化合物、喔啉类化合物、二氮蒽类化合物、含硅杂环类化合物、喹啉类化合物、菲啰啉类化合物、金属螯合物(如Alq3)、氟取代苯类化合物、苯并咪唑类化合物。
本发明有机电致发光器件的电子注入层,可以有效地把电子从阴极注入到有机层中,主要选自碱金属或者碱金属的化合物,或选自碱土金属或者碱土金属的化合物或者碱金属络合物,可以选择如下化合物,但是不限于此:碱金属、碱土金属、稀土金属、碱金属的氧化物或者卤化物、碱土金属的氧化物或者卤化物、稀土金属的氧化物或者卤化物、碱金属或者碱土金属的有机络合物;优选为锂、氟化锂、氧化锂、氮化锂、8-羟基喹啉锂、铯、碳酸铯、8-羟基喹啉铯、钙、氟化钙、氧化钙、镁、氟化镁、碳酸镁、氧化镁,这些化合物可以单独使用也可以混合物使用,也可以跟其他有机电致发光材料配合使用。
本发明的有机电致发光器件中有机层的每一层,可以通过真空蒸镀法、分子束蒸镀法、溶于溶剂的浸涂法、旋涂法、棒涂法或者喷墨打印等方式制备。对于金属电机可以使用蒸镀法或者溅射法进行制备。
器件实验表明,本发明如结构式I所述的基于菲和咔唑的化合物,具有较好热稳定性、高发光效率、高发光纯度。采用该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
图1为本发明的一种有机电致发光器件结构示意图,
其中,110为玻璃基板,120为阳极,130为空穴注入层,140为空穴传输层,150为阻挡层,160为发光层,170为电子传输层,180为电子注入层,190为阴极。
具体实施方式
为了更详细叙述本发明,特举以下例子,但是不限于此。
实施例1
化合物1的合成路线
中间体1-1的合成方法
在烧瓶中,加入9,10-二溴菲(16g,48mmol),9-苯基-3-咔唑硼酸(13.8g,48mmol),碳酸钾(13.6g,100mmol),四三苯基膦钯(0.5g),四氢呋喃(200mL)和水(100mL),在氮气保护下加热回流12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12.5g,产率52%。
化合物1的合成方法
在烧瓶中,加入中间体1(1.5g,3mmol),3-吡啶硼酸(0.8g,4mmol),碳酸钾(0.8g,6mmol),四三苯基膦钯(50mg),四氢呋喃(20mL)和水(10mL),在氮气保护下加热回流12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1.1g,产率74%。
实施例2
化合物8的合成路线
中间体8-1的合成方法
在烧瓶中,加入中间体1-1(8g,16mmol),无水四氢呋喃(100mL),氮气保护下冷却至-78℃,缓慢加入2.5M正丁基正己烷溶液(19mmol,7.8mL),反应1小时,再加入硼酸三异丙酯(21mmol,3.9g),缓慢升至室温反应12小时,然后加稀盐酸调节pH至小于7,用二氯甲烷萃取,干燥,浓缩,粗产物用正己烷搅拌,过滤,干燥得到产物5.9g,产率79%。
化合物8的合成方法
合成方法跟化合物1的合成一样,所用原料为中间体8-1和3,5-二苯基-2-氯三嗪,产率64%。
实施例3
化合物16的合成路线
合成方法跟化合物1的合成方法一样,所用原料为中间体8-1和4-(4-溴苯基)-2,6-二苯基嘧啶,产率为72%。
实施例4
化合物25的合成路线
合成方法跟化合物1的合成方法一样,所用原料为中间体8-1和2-(3-溴苯基)-5,5-二苯基三嗪,产率75%。
实施例5
化合物27的合成路线
合成方法跟化合物1的合成一样,所用原料为中间体1-1和B-[4-(1-苯基-1H-苯并咪唑-2-基)苯基]-硼酸,产率81%。
实施例6
化合物35的合成路线
中间体35-1的合成方法
合成方法跟中间体1-1的合成一样,所用原料为9,10-二溴菲和4-(9-咔唑基)苯基-硼酸,产率56%。
化合物35的合成方法
合成方法跟化合物1的合成一样,所用原料为中间体35-1和3-吡啶频哪醇酯,产率77%。
实施例7
化合物44的合成路线
中间体44-1的合成方法
合成方法跟中间体8-1的合成一样,所用原料为中间体35-1,产率68%。
化合物44的合成方法
合成方法跟化合物1的合成一样,所用原料为中间体44-1和4-(3-吡啶基)-溴苯,产率75%。
实施例8
化合物59的合成路线
合成方法跟化合物1的合成一样,所用原料为中间体44-1和2-(3-溴苯基)-5,5-二苯基三嗪,产率82%。
实施例9
化合物61的合成路线
合成方法跟化合物1的合成一样,所用原料为中间体35-1和B-[4-(1-苯基-1H-苯并咪唑-2-基)苯基]-硼酸,产率85%。
实施例10
化合物64的合成路线
合成方法跟化合物1的合成一样,所用原料为中间体35-1和4-(2-苯基-1H-苯并咪唑-1-基)苯基]硼酸,产率69%。
实施例11-20
有机电致发光器件的制备
使用实施例的化合物制备OLED
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上蒸镀3nm厚的MnO3(氧化钼)为空穴注入层130。
然后,在空穴注入层上蒸镀50nm厚的TAPC为空穴传输材料140。
然后,蒸镀TCTA,形成5nm厚的电子阻挡层150。
然后,在电子阻挡层上蒸镀20nm厚的发光层160,其中,本发明化合物为主体发光材料,而以重量比值为3%的Ir(ppy)3作为磷光掺杂客体材料。
然后,在发光层上蒸镀40nm厚的BmPYPB作为电子传输层170。
最后,蒸镀1nm LiF为电子注入层180和80nm Al作为器件阴极190。
所制备的器件(结构示意图见图1)用Photo Research PR650光谱仪测得的在5000cd/m2的亮度下的电流效率为如表1。
比较例1
比较例制备器件的方法跟实施例11-20器件制备方法一样,除了用CBP代替本发明化合物作为主体材料外。
表1
实施例 | 化合物 | 电流效率(cd/A) | 发光颜色 |
11 | 1 | 52 | 绿光 |
12 | 8 | 53 | 绿光 |
13 | 16 | 56 | 绿光 |
14 | 25 | 57 | 绿光 |
15 | 27 | 55 | 绿光 |
16 | 35 | 56 | 绿光 |
17 | 44 | 54 | 绿光 |
18 | 59 | 54 | 绿光 |
19 | 61 | 57 | 绿光 |
20 | 64 | 56 | 绿光 |
比较例1 | CBP | 45 | 绿光 |
器件中所述化合物的结构式如下:
从表1中可以看出,本发明的化合物用于有机电致发光器件,可以降低工作电压,提高器件效率,是具有优良性能的磷光主体材料。如上所述,本发明的化合物具有高的稳定性,制备的有机电致发光器件具有高的效率和光纯度。
以上详细描述了本发明的较佳具体实施例。应当理解,本领域的普通技术人员无需创造性劳动就可以根据本发明的构思作出诸多修改和变化。因此,凡本技术领域中技术人员依本发明的构思在现有技术的基础上通过逻辑分析、推理或者有限的实验可以得到的技术方案,皆应在由权利要求书所确定的保护范围内。
Claims (10)
1.一种基于菲和咔唑的化合物,其特征在于,为具有如下结构式I的化合物:
其中,Ar1选自取代或者未取代的C6-C30的芳基;
Ar2选自取代或者未取代的C3-C30的杂芳基、取代或者未取代的C3-C30的芳膦基;
R1-R8独立地选自氢、氘、C1-C12的烷基、C1-C8的烷氧基、取代或者未取代的C6-C30的芳基。
2.如权利要求1所述的基于菲和咔唑的化合物,其特征在于,Ar1选自苯基、氰基苯基、氟取代苯基、联苯基、二苯基取代苯基、萘基、三并苯基、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。
3.如权利要求1所述的基于菲和咔唑的化合物,其特征在于,Ar2选自吡啶基、嘧啶基、哒嗪基、三嗪基、咪唑基、噁唑基、噻唑基、噻二唑基、喹啉基、异喹啉基、喹唑啉基、喹喔啉基、氮杂二苯并呋喃基、氮杂二苯并噻吩基、咪唑基,以上芳基和杂芳基还可以进一步为C1-C12的烷基取代。
4.如权利要求1所述的基于菲和咔唑的化合物,其特征在于,R1-R8独立地选自氢、苯基、甲基。
5.如权利要求1所述的基于菲和咔唑的化合物,其特征在于,为下列结构式1-68的化合物:
6.权利要求1所述的基于菲和咔唑的化合物在有机电致发光器件中的应用。
7.一种有机电致发光器件,该器件包含阳极、阴极和有机层,有机层包含发光层、空穴注入层、空穴传输层、激子阻挡层、电子传输层中的至少一层,其特征在于,所述有机层中至少一层含有如权利要求1所述的基于菲和咔唑的化合物。
8.如权利要求7所述的有机电致发光器件,其特征在于,如结构式I所述的基于菲和咔唑的化合物所在的有机层为发光层。
9.如权利要求7所述的有机电致发光器件,其特征在于,如结构式I所述的基于菲和咔唑的化合物单独使用其中的一种化合物,或者同时使用结构式I中的两种或两种以上的化合物。
10.如权利要求7所述的有机电致发光器件,其特征在于,所述有机层的总厚度为1-1000nm。
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111205269A (zh) * | 2020-01-10 | 2020-05-29 | 上海百豪新材料有限公司 | 基于咔唑的有机电致磷光材料组成物制备方法及应用制备 |
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102918037A (zh) * | 2010-06-02 | 2013-02-06 | 捷恩智株式会社 | 具有含接受电子的氮的杂芳基的取代基的咔唑化合物及有机电激发光元件 |
CN106033798A (zh) * | 2015-03-09 | 2016-10-19 | 广东阿格蕾雅光电材料有限公司 | 有机电致发光器件 |
-
2017
- 2017-12-26 CN CN201711435598.7A patent/CN108299389A/zh active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102918037A (zh) * | 2010-06-02 | 2013-02-06 | 捷恩智株式会社 | 具有含接受电子的氮的杂芳基的取代基的咔唑化合物及有机电激发光元件 |
CN106033798A (zh) * | 2015-03-09 | 2016-10-19 | 广东阿格蕾雅光电材料有限公司 | 有机电致发光器件 |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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TWI761014B (zh) * | 2020-01-08 | 2022-04-11 | 大陸商上海傳勤新材料有限公司 | 一種含有氮原子雜環的有機電子材料及其製備方法和應用 |
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