CN106495975B - 9,9′-联蒽类蓝光多功能材料及其应用 - Google Patents
9,9′-联蒽类蓝光多功能材料及其应用 Download PDFInfo
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- SXGIRTCIFPJUEQ-UHFFFAOYSA-N 9-anthracen-9-ylanthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C(C=3C4=CC=CC=C4C=C4C=CC=CC4=3)=C21 SXGIRTCIFPJUEQ-UHFFFAOYSA-N 0.000 title abstract description 24
- 239000007777 multifunctional material Substances 0.000 title abstract description 10
- 239000000463 material Substances 0.000 claims abstract description 141
- 230000005540 biological transmission Effects 0.000 claims abstract description 4
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 claims description 43
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 claims description 43
- 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 claims description 43
- 239000000758 substrate Substances 0.000 claims description 35
- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 claims description 26
- 238000002347 injection Methods 0.000 claims description 26
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 230000000903 blocking effect Effects 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
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- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- YTPSFXZMJKMUJE-UHFFFAOYSA-N 2-tert-butylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)(C)C)=CC=C3C(=O)C2=C1 YTPSFXZMJKMUJE-UHFFFAOYSA-N 0.000 claims description 2
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- JUTIJVADGQDBGY-UHFFFAOYSA-N anthracene photodimer Chemical compound C12=CC=CC=C2C2C(C3=CC=CC=C33)C4=CC=CC=C4C3C1C1=CC=CC=C12 JUTIJVADGQDBGY-UHFFFAOYSA-N 0.000 abstract description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- -1 dianilino) Chemical group 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000021615 conjugation Effects 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
- 239000013078 crystal Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
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- 239000010409 thin film Substances 0.000 description 1
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Abstract
本发明公开了一种9,9′‑联蒽类蓝光多功能材料及其应用。本发明通过不同的给电子基团和吸电子基团取代联蒽上的氢原子,通过改变取代基的性质、位置和数目,利用取代基的空间效应和电子效应不仅能够调节材料的最高占据轨道和最低空轨道能级,而且改善材料的发光性能、电荷传输性能以及稳定性。该类材料不仅可以作为深蓝光主体材料,还可以作为发光材料,均具有优异的器件性能。且材料易于合成、提纯方便,可广泛应用于有机场效应晶体管,有机电致发光器件和有机光伏太阳能电池领域。
Description
技术领域
本发明属于有机光电功能材料技术领域,涉及一种蓝光多功能材料,尤其是一种9,9′-联蒽类蓝光主体材料和发光材料及其应用。
背景技术
自从1987年柯达公司的邓青云博士等人首次研制出具有使用价值的低驱动电压有机电致发光器件(OLEDs)以来,便引起了各国科研工作者的极大重视而成为当今显示领域的研究热点。有机电致发光器件展示了下一代平板显示和固态照明方面的应用潜能,主要是因为具有发光效率高、驱动电压低、主动式发光、亮度高、视角宽、响应速度快、可实现全彩平板显示等优点。在OLEDs的研究中,对于全彩显示和白光所需要红,绿,蓝三基色中,由于蓝光材料内在的宽带隙使得很难实现高效率和良好色纯度以及长寿命的蓝光器件。因此,相对于绿光和红光器件,蓝光器件的性能较差。尽管磷光电致发光器件(PhOLEDs)已有大量的研究,但是维持高效和长寿命的性能对磷光蓝光器件却很难。因此,在全彩显示方面,蓝光荧光材料仍具有重要作用(Nature 2006, 440, 908; Appl. Phys. Lett. 2008,92, 053311; Appl. Phys. Lett. 2008, 93, 073304;J. Mater. Chem. C, 2011, 21,13640)。在OLEDs中主体掺杂客体材料发光可以有效避免荧光浓度猝灭,改善器件电致发光(EL)和发光颜色等方面的性能(J. Appl. Phys. 1989, 65, 3610)。目前多种非掺杂蓝光主体材料有了进一步的研究,包括:蒽、芴、苯乙烯亚芳、芘、喹啉和苯亚菲衍生物。其中以蒽为核心的荧光材料广泛被人关注,因为它具有宽能带,高荧光量子效率,良好的热稳定性及双极性电子传输性能。然而能符合国际电视标准委员会(National Television SystemCommittee, NTSC) 制定的蓝光CIE(0.14,0.08)标准的OLEDs很少,所以深蓝器件(CIEy<0.08)的研究意义重大,同时,蓝光材料的效率、色纯度和器件寿命还需进一步的改善,特别重要的是开发具有良好热稳定性和形态稳定性以及高发光效率的蓝光材料。
联蒽类材料具有荧光量子效率高、成膜性好和稳定性高等优点。9,9′-联蒽是两个蒽分子在9,9′-位通过单键相连,晶体数据表明由于1,1’和8,8’位的氢原子强烈的排斥作用,两个蒽分子几乎彼此垂直(二面角为89.4°)(J. Mater. Chem. 2008, 18, 3376; Org.Electron. 2009, 10, 822),在基态的正交结构导致联蒽电子耦合,而激发态的化学结构表现出强烈的电子相互作用,形成了特殊的分子内电荷转移(ICT)特性,这种扭曲的电荷转移特性通过分子内从电荷转移激子向单线态激子的转换实现了电子空穴的复合,使单线态激子的比例大于25%,从而突破荧光外量子效率5% 的限制(Org. Electron. 2013, 14,915)。同时庞大的取代基团中的位阻效应能有效阻止分子间共轭,在固态堆积时有效避免荧光浓度猝灭,提高器件的电致发光性能(J. Mate. Chem. C, 2013, 1, 8117)。
发明内容
本发明的目的在于提供一种9,9′-联蒽类蓝光多功能材料及其应用,该材料具有良好的热稳定性和发光性能,且材料易于合成、提纯方便,可广泛用于有机场效应晶体管,有机电致发光器件和有机光伏太阳能电池等领域。
本发明是采用如下技术方案实现的:
一种9,9′-联蒽类蓝光多功能材料,具有以下分子结构式:
上述分子式中,R1—R4 分别是氢,烷基CnH2n+1(如甲基、乙基、丙基、异丙基、丁基、叔丁基...n≧1),烯烃基CmH2m-1(如乙烯基、丙烯基...m≧2),芳香基(如苯基、甲苯基、萘基、蒽基、芘基、苝基),芳胺基(如二苯胺基),以及甲氧基、氰基、羟基、氟和三氟甲基。
进一步的,以上所述基团都是在联蒽的2, 2′, 3, 3′, 6, 6′, 7, 7′位上进行取代,取代基的数目是1,2,3或4。
上述9,9′-联蒽类蓝光多功能材料的制备方法如下:
在氮气氛围中,取相应蒽醌衍生物原料、锌粉、冰醋酸,依次加入容器中,加热搅拌,维持温度在80~100℃,缓慢滴加浓盐酸,滴加完毕,逐渐有固体析出,反应12~15h,停止反应;冷却,过滤,甲苯纯化,烘干得到固体,即9,9′-联蒽类蓝光材料。
基于上述9,9′-联蒽类蓝光多功能材料,制备以下电致发光器件:
一种电致发光器件,采用9,9′-联蒽类蓝光材料作为发光材料,HAT-CN作为空穴注入材料,TAPC作为空穴传输材料,TPBI作为电子传输及激子阻挡材料,Liq作为电子注入材料,制备的电致发光器件结构如下:
玻璃基片/ITO/HAT-CN (5nm)/TAPC (40nm)/发光材料 (20nm)/TPBI (40nm)/Liq(1 nm)/Al (120nm)。
一种电致发光掺杂器件,采用9,9′-联蒽类蓝光材料掺杂3%的DSA-ph材料作为发光材料,HAT-CN作为空穴注入材料,TAPC作为空穴传输材料,TPBI作为电子传输及激子阻挡材料,Liq作为电子注入材料,制备的电致发光器件结构如下:
玻璃基片/ITO/HAT-CN (5nm)/TAPC (40nm)/ 9,9′-联蒽类蓝光材料:3%DSA-ph(20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm)。
另一种电致发光掺杂器件,采用CBP材料掺杂5%的9,9′-联蒽类蓝光材料为发光材料,HAT-CN作为空穴注入材料,TAPC作为空穴传输材料,TPBI作为电子传输及激子阻挡材料,Liq作为电子注入材料,制备的电致发光器件结构如下:
玻璃基片/ITO/HAT-CN (5nm)/TAPC (40nm)/CBP:5%9,9′-联蒽类蓝光材料(20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm)。
上述电致发光器件的制备方法如下:
(1)、预刻有ITO的玻璃基板的清洗:利用热的洗涤剂超声和去离子水超声的方法对透明导电基片ITO玻璃进行清洗,清洗后将其放置在红外灯下烘干,其中导电基片上面的ITO膜作为器件的阳极层,ITO膜的方块电阻为5Ω~100Ω,膜厚为100nm;
(2)、各有机功能层的制备:把做干燥处理后的基片放入到真空腔内,依次蒸镀规定厚度的空穴注入材料、空穴传输材料、发光材料、电子传输及激子阻挡材料,薄膜的蒸镀速率为0.1~0.3nm·s–1;
(3)、阴极的制备:保持上述真空腔内压力不变,在上述电子传输层之上依次蒸镀1nm的Liq和120nm的Al复合阴极层。
将做好的器件拿出真空腔室,在大气环境下测试器件的电流-电压-亮度-效率特性以及电致发光光谱。
本发明还提出9,9′-联蒽类蓝光主体材料和发光材料在有机电致发光器件和有机光伏太阳能电池中的应用。
本发明具有以下有益效果:
1、本发明的9,9′-联蒽类蓝光主体材料通过改变联蒽基团上取代基性质、位置和数目,调节材料的最高占据轨道和最低空轨道能级,并使其发射光谱与客体DSA-ph的吸收光谱有很好的重叠,因而能有效地吸收能量并将能量转移给客体,从而引起客体的发光,使得器件发光亮度明显提高。
2、本发明的9,9′-联蒽类蓝光材料具有良好的热稳定性,优秀的玻璃化温度以及良好的成膜能力;同时具有合适的的最高占据轨道和最低空轨道能级,在溶液和薄膜中都有较好的荧光和较窄的光谱半高宽(FWHM),荧光量子效率高。
3、利用本发明的9,9′-联蒽类蓝光主体材料制备的非掺杂的深蓝光发光器件,能够得到很好的光谱的色坐标 (0.15–0.16, 0.06–0.10),其对应的发光峰在450nm附近,同时具有低启亮电压、高电流效率、高能量效率和高外量子效率。
4、利用本发明的9,9′-联蒽类蓝光发光材料配合合适的主体(CBP)制备的深蓝光发光器件,能够实现深蓝光发射,其色坐标(0.16,0.06)以及具有低启亮电压、高电流效率、高能量效率和高外量子效率。
5、利用本发明的9,9′-联蒽类蓝光主体材料与DSA-ph掺杂制备的蓝光发光器件具有低启亮电压、高亮度、高电流效率、高能量效率和高外量子效率。
本发明设计合理,通过不同的给电子基团和吸电子基团取代联蒽上的氢原子,通过改变取代基的性质、位置和数目,利用取代基的空间效应和电子效应不仅能够调节材料的最高占据轨道和最低空轨道能级,而且改善材料的发光性能、电荷传输性能以及稳定性。该类材料不仅可以作为深蓝光主体材料,还可以作为发光材料,均具有优异的器件性能。且材料易于合成、提纯方便,可广泛应用于有机场效应晶体管,有机电致发光器件和有机光伏太阳能电池领域。
附图说明
图1 表示本发明提供的9,9′-联蒽类多功能材料的分子结构示意图。
图2 表示材料MBA所制备的非掺杂器件ITO/HAT-CN (5nm)/TAPC (40nm)/MBA(20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm) 的电流密度-电压-亮度曲线图。
图3 表示材料MBA所制备的非掺杂器件ITO/HAT-CN (5nm)/TAPC (40nm)/MBA(20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm)的电流效率-电流密度-能量效率曲线图。
图4 表示材料MBA作为蓝光主体所制备的掺杂器件ITO/HAT-CN (5nm)/TAPC(40nm)/MBA: 3%DSA-ph (20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm)的电流密度-电压-亮度曲线图。
图5 表示材料MBA作为蓝光主体所制备的掺杂器件ITO/HAT-CN (5nm)/TAPC(40nm)/MBA:3%DSA-ph (20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm)的电流效率-电流密度-能量效率曲线图。
图6 表示材料TBBA作为蓝光主体所制备的非掺杂器件ITO/HAT-CN (5nm)/TAPC(40nm)/TBBA (20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm)的电流密度-电压-亮度曲线图;
图7 表示材料TBBA作为蓝光主体所制备的非掺杂器件ITO/HAT-CN (5nm)/TAPC(40nm)/TBBA (20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm)的电流效率-电流密度-能量效率曲线图。
图8 表示材料TBBA作为蓝光主体所制备的掺杂器件ITO/HAT-CN (5nm)/TAPC(40nm)/TBBA:3%DSA-ph (20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm) 的电流密度-电压-亮度曲线图。
图9 表示材料TBBA作为蓝光主体所制备的掺杂器件ITO/HAT-CN (5nm)/TAPC(40nm)/TBBA:3%DSA-ph (20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm)的电流效率-电流密度-能量效率曲线图。
图10表示材料MBA作为蓝光发光材料与主体(CBP)所制备的掺杂器件ITO/HAT-CN(5nm)/TAPC (40nm)/CBP:5%MBA (20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm)的电流密度-电压-亮度曲线图。
图11表示材料MBA作为蓝光发光材料与主体(CBP)所制备的掺杂器件ITO/HAT-CN(5nm)/TAPC (40nm)/CBP:5%MBA (20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm)的电流效率-电流密度-能量效率曲线图。
图12 表示图1中联蒽材料MBA和TBBA的荧光发射光谱。
具体实施方式
一种9,9′-联蒽类蓝光多功能材料,具有以下分子结构式:
上述分子式中,R1—R4分别是氢,烷基CnH2n+1(如甲基、乙基、丙基、异丙基、丁基、叔丁基...n≧1),烯烃基CmH2m-1(如乙烯基、丙烯基...m≧2),芳香基(如苯基、甲苯基、萘基、蒽基、芘基、苝基),芳胺基(如二苯胺基),以及甲氧基、氰基、羟基、氟和三氟甲基。其中,上述基团都是在联蒽的2, 2′, 3, 3′, 6, 6′, 7, 7′位上进行取代,取代基的数目是1, 2, 3或4。
进一步的,R1—R4的具体分布如下:
该类材料在有机电致发光器件和有机光伏太阳能电池中具有潜在的应用。
下面结合实施例和附图对本发明做进一步详细描述:
实施例1
甲基取代的9,9′-联蒽蓝光材料(MBA)的合成:
在氮气氛围中,取2-甲基蒽醌60mmol(13.32 g),锌粉346mmol(22.5g),冰醋酸300mL,依次加入500mL三孔圆颈烧瓶中,加热搅拌,维持温度在80~100℃,缓慢滴加浓盐酸70mL,滴加完毕,颜色逐渐变成淡黄色,逐渐有固体析出,反应15h,点板确定没有原料存在,停止反应。冷却,过滤,甲苯纯化,烘干得到淡黄色固体9g,产率78%。1H NMR (400 MHz,CDCl3):δ8.58 – 8.47 (m, 2H), 8.08 – 7.80 (m, 4H), 7.39 – 7.30 (m, 2H), 7.07 –6.96 (m, 4H), 6.95 – 6.88 (m, 4H), 2.54 – 2.30 (m, 6H)。
实施例2
叔丁基取代的9,9′-联蒽蓝光材料(TBBA)的合成:
在氮气氛围中,取2-叔丁基蒽醌60mmol(15.84 g),锌粉346mmol(22.5g),冰醋酸300mL,依次加入500mL三孔圆颈烧瓶中,加热搅拌,维持温度在80~100℃,缓慢滴加浓盐酸70mL,滴加完毕,颜色逐渐变成白色,逐渐有固体析出,反应15h,点板确定没有原料存在,停止反应。冷却,过滤,甲苯纯化,烘干得到白色固体12g,产率90%。1H NMR (400 MHz, CDCl3):δ8.70 – 8.56 (m, 2H), 8.19 – 8.00 (m, 4H), 7.61 – 7.00 (m, 10H), 1.60 –1.35(m, 18H)。
实施例3
一种电致发光器件,采用材料MBA为蓝光发光材料,HAT-CN作为空穴注入材料,TAPC作为空穴传输材料,TPBI作为电子传输及激子阻挡材料,Liq作为电子注入材料,制备的电致发光器件结构如下:
玻璃基片/ITO/HAT-CN (5nm)/TAPC (40nm)/MBA (20nm)/TPBI (40nm)/Liq(1nm)/Al (120nm)。
具体制备方法如下:
(1)、预刻有ITO的玻璃基板的清洗:利用热的洗涤剂超声和去离子水超声的方法对透明导电基片ITO玻璃进行清洗,清洗后将其放置在红外灯下烘干,其中导电基片上面的ITO膜作为器件的阳极层,ITO膜的方块电阻为5Ω~100Ω,膜厚为100nm左右。
(2)、各有机功能层的制备:把做干燥处理后的基片放入到真空腔内,依次蒸镀5nm的HAT-CN、40nm的TAPC、20nm的MBA和40nm的TPBI,薄膜的蒸镀速率为0.1~0.3nm s–1。
(3)、阴极的制备:保持上述真空腔内压力不变,在上述电子传输层之上依次蒸镀1nm的Liq和120nm的Al复合阴极层。
(4)、将做好的器件拿出真空腔室,在大气环境下测试器件的电流-电压-亮度-效率特性以及电致发光光谱。
图2为材料MBA所制备的非掺杂器件ITO/HAT-CN (5nm)/TAPC (40nm)/MBA(20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm)的电流密度-电压-亮度曲线图,启亮电压为3.1 V,最大发光亮度可达3546 cd m–1。
图3为材料MBA所制备的非掺杂器件ITO/HAT-CN (5nm)/TAPC (40nm)/MBA(20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm)的电流效率-电流密度-能量效率曲图,其最大电流效率为2.26 cd A–1,最大能量效率为1.92 lm W–1,最大外量子效率为2.51%,CIE坐标(0.15,0.10)。
实施例4
一种电致发光掺杂器件,采用材料MBA掺杂3%的DSA-ph作为发光材料,HAT-CN作为空穴注入材料,TAPC作为空穴传输材料,TPBI作为电子传输及激子阻挡材料,Liq作为电子注入材料,制备的电致发光器件结构如下:
玻璃基片/ITO/HAT-CN (5nm)/TAPC (40nm)/材料MBA:3%DSA-ph (20nm)/TPBI(40nm)/Liq (1nm)/Al (120nm)。
制备方法同实施例3。
图4是材料MBA作为蓝光主体所制备的掺杂器件ITO/HAT-CN (5nm)/TAPC (40nm)/MBA:3%DSA-ph (20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm)的电流密度-电压-亮度曲线图,启亮电压为3.0V,最大发光亮度可达13800 cd m–1。
图5是材料MBA作为蓝光主体所制备的掺杂器件ITO/HAT-CN (5nm)/TAPC (40nm)/MBA:3%DSA-ph (20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm)的电流效率-电流密度-能量效率曲线图,其最大电流效率为16.54 cd A–1,最大能量效率为16.57 lm W–1,最大外量子效率为9.30%,其最大发光峰为448nm,表现出较高的电致发光性能。
实施例5
一种电致发光器件,采用材料TBBA作为发光材料,HAT-CN作为空穴注入材料,TAPC作为空穴传输材料,TPBI作为电子传输及激子阻挡材料,Liq作为电子注入材料,制备的电致发光器件结构如下:
玻璃基片/ITO/HAT-CN (5nm)/TAPC (40nm)/TBBA (20nm)/TPBI (40nm)/Liq(1nm)/Al (120nm)。
制备方法同实施例3。
图6为材料TBBA所制备的非掺杂器件ITO/HAT-CN (5nm)/TAPC (40nm)/TBBA(20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm)的电流密度-电压-亮度曲线图,启亮电压为2.9 V,最大发光亮度可达2013 cd m–1。
图7为材料TBBA所制备的非掺杂器件ITO/HAT-CN (5nm)/TAPC (40nm)/TBBA(20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm)的电流效率-电流密度-能量效率曲线图,其最大电流效率为2.52 cd A–1,最大能量效率为2.73 lm W–1,最大外量子效率为3.18%,尤其CIE坐标(0.15,0.06),实现深蓝光发射。
实施例6
一种电致发光掺杂器件,采用材料TBBA掺杂3%的DSA-ph作为发光材料,HAT-CN作为空穴注入材料,TAPC作为空穴传输材料,TPBI作为电子传输及激子阻挡材料,Liq作为电子注入材料,制备的电致发光器件结构如下:
玻璃基片/ITO/HAT-CN (5nm)/TAPC (40nm)/TBBA:3%DSA-ph (20nm)/TPBI(40nm)/Liq (1 nm)/Al (120nm)。
制备方法同实施例3。
图8是材料TBBA作为蓝光主体所制备的掺杂器件ITO/HAT-CN (5nm)/TAPC(40nm)/TBBA:3%DSA-ph (20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm)的电流密度-电压-亮度曲线图,启亮电压为2.9 V,最大发光亮度可高达10900 cd m–1。
图9是材料TBBA作为蓝光主体所制备的掺杂器件ITO/HAT-CN (5nm)/TAPC(40nm)/TBBA:3%DSA-ph (20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm)的电流效率-电流密度-能量效率曲图,其最大电流效率为11.33 cd A–1,最大能量效率为10.45 lm W–1,最大外量子效率为6.92%。
实施例7
一种电致发光掺杂器件,采用CBP掺杂5%MBA材料作为发光材料,HAT-CN作为空穴注入材料,TAPC作为空穴传输材料,TPBI作为电子传输及激子阻挡材料,Liq作为电子注入材料,制备的电致发光器件结构如下:
玻璃基片/ITO/HAT-CN (5nm)/TAPC (40nm)/CBP:5%MBA (20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm)。
制备方法同实施例3。
图10是材料MBA作为蓝光发光材料配合主体(CBP)所制备的掺杂器件ITO/HAT-CN(5nm)/TAPC (40nm)/CBP:5%MBA (20nm)/TPBI (40nm)/Liq (1nm)/Al (120nm)的电流密度-电压-亮度曲线图;其最大发光亮度为3175 cd A–1。
图11是材料MBA作为蓝光发光材料配合主体(CBP)所制备的掺杂器件ITO/HAT-CN(5nm)/TAPC (40nm)/CBP:5%MBA (20nm)/TPBI (40nm)/Liq (1 nm)/Al (120 nm)的电流效率-电流密度-能量效率曲线图;其最大电流效率为2.76 cd A–1,最大能量效率为2.40 lmW–1,最大外量子效率为3.6%,尤其CIE坐标(0.16, 0.06),实现深蓝光发射。
图12为MBA和TBBA的荧光发射光谱,其发射峰在450 nm附近。
最后所应说明的是,以上实施例仅用以说明本发明的技术方案而非限制,尽管参照本发明实施例进行了详细说明,本领域的普通技术人员应当理解,对本发明的技术方案进行修改或者等同替换,都不脱离本发明的技术方案的精神和范围,其均应涵盖权利要求保护范围中。
Claims (3)
1.一种电致发光器件,其特征在于:采用材料MBA掺杂3%的DSA-ph作为发光材料,HAT-CN作为空穴注入材料,TAPC作为空穴传输材料,TPBI作为电子传输及激子阻挡材料,Liq作为电子注入材料,制备的电致发光器件结构如下:
玻璃基片/ITO/HAT-CN 5nm/TAPC 40nm/材料MBA:3%DSA-ph 20nm/TPBI 40nm/Liq1nm/Al 120nm;
所述MBA的合成:在氮气氛围中,取2-甲基蒽醌13.32g,锌粉22.5g,冰醋酸300mL,依次加入500mL三孔圆颈烧瓶中,加热搅拌,维持温度在80~100℃,缓慢滴加浓盐酸70mL,滴加完毕,颜色逐渐变成淡黄色,逐渐有固体析出,反应15h,点板确定没有原料存在,停止反应;冷却,过滤,甲苯纯化,烘干得到淡黄色固体9g,产率78%;
器件制备方法如下:
(1)、预刻有ITO的玻璃基板的清洗:利用洗涤剂超声和去离子水超声的方法对透明导电基片ITO玻璃进行清洗,清洗后将其放置在红外灯下烘干,其中导电基片上面的ITO膜作为器件的阳极层,ITO膜的方块电阻为5Ω~100Ω,膜厚为100nm;
(2)、各有机功能层的制备:把做干燥处理后的基片放入到真空腔内,依次蒸镀空穴注入材料、空穴传输材料、发光材料、电子传输及激子阻挡材料,薄膜的蒸镀速率为0.1~0.3nm·s–1;
(3)、阴极的制备:保持上述真空腔内压力不变,在上述电子传输层之上依次蒸镀1nm的Liq和120nm的Al复合阴极层。
2.一种电致发光掺杂器件,其特征在于:采用材料TBBA掺杂3%的DSA-ph作为发光材料,HAT-CN作为空穴注入材料,TAPC作为空穴传输材料,TPBI作为电子传输及激子阻挡材料,Liq作为电子注入材料,制备的电致发光器件结构如下:
玻璃基片/ITO/HAT-CN 5nm/TAPC 40nm/TBBA:3%DSA-ph 20nm/TPBI 40nm/Liq 1nm/Al120nm;
所述TBBA的合成:在氮气氛围中,取2-叔丁基蒽醌15.84g,锌粉22.5g,冰醋酸300mL,依次加入500mL三孔圆颈烧瓶中,加热搅拌,维持温度在80~100℃,缓慢滴加浓盐酸70mL,滴加完毕,颜色逐渐变成白色,逐渐有固体析出,反应15h,点板确定没有原料存在,停止反应;冷却,过滤,甲苯纯化,烘干得到白色固体12g,产率90%;
器件制备方法如下:
(1)、预刻有ITO的玻璃基板的清洗:利用洗涤剂超声和去离子水超声的方法对透明导电基片ITO玻璃进行清洗,清洗后将其放置在红外灯下烘干,其中导电基片上面的ITO膜作为器件的阳极层,ITO膜的方块电阻为5Ω~100Ω,膜厚为100nm;
(2)、各有机功能层的制备:把做干燥处理后的基片放入到真空腔内,依次蒸镀空穴注入材料、空穴传输材料、发光材料、电子传输及激子阻挡材料,薄膜的蒸镀速率为0.1~0.3nm·s–1;
(3)、阴极的制备:保持上述真空腔内压力不变,在上述电子传输层之上依次蒸镀1nm的Liq和120nm的Al复合阴极层。
3.一种电致发光掺杂器件,其特征在于:采用CBP掺杂5%MBA材料作为发光材料,HAT-CN作为空穴注入材料,TAPC作为空穴传输材料,TPBI作为电子传输及激子阻挡材料,Liq作为电子注入材料,制备的电致发光器件结构如下:
玻璃基片/ITO/HAT-CN 5nm/TAPC 40nm/CBP:5%MBA 20nm/TPBI 40nm/Liq 1nm/Al120nm;
所述MBA的合成:在氮气氛围中,取2-甲基蒽醌13.32g,锌粉22.5g,冰醋酸300mL,依次加入500mL三孔圆颈烧瓶中,加热搅拌,维持温度在80~100℃,缓慢滴加浓盐酸70mL,滴加完毕,颜色逐渐变成淡黄色,逐渐有固体析出,反应15h,点板确定没有原料存在,停止反应;冷却,过滤,甲苯纯化,烘干得到淡黄色固体9g,产率78%;
器件制备方法如下:
(1)、预刻有ITO的玻璃基板的清洗:利用洗涤剂超声和去离子水超声的方法对透明导电基片ITO玻璃进行清洗,清洗后将其放置在红外灯下烘干,其中导电基片上面的ITO膜作为器件的阳极层,ITO膜的方块电阻为5Ω~100Ω,膜厚为100nm;
(2)、各有机功能层的制备:把做干燥处理后的基片放入到真空腔内,依次蒸镀空穴注入材料、空穴传输材料、发光材料、电子传输及激子阻挡材料,薄膜的蒸镀速率为0.1~0.3nm·s–1;
(3)、阴极的制备:保持上述真空腔内压力不变,在上述电子传输层之上依次蒸镀1nm的Liq和120nm的Al复合阴极层。
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