CN108503655A - 一种杂环化合物及使用该杂环化合物的有机电子装置 - Google Patents
一种杂环化合物及使用该杂环化合物的有机电子装置 Download PDFInfo
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- CN108503655A CN108503655A CN201710204094.8A CN201710204094A CN108503655A CN 108503655 A CN108503655 A CN 108503655A CN 201710204094 A CN201710204094 A CN 201710204094A CN 108503655 A CN108503655 A CN 108503655A
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- organic
- heterocyclic compound
- layer
- electronic device
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- 239000004065 semiconductor Substances 0.000 claims abstract description 32
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 16
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- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
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Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
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Abstract
本发明公开了由下式(I)表示的一种杂环化合物,以及使用该杂环化合物的有机电子装置,其具有良好的性能。此外,本发明的杂环化合物更适用于有机半导体装置、钙钛矿太阳能电池装置以及有机电发光装置(有机EL装置)。
Description
技术领域
本发明涉及一种杂环化合物以及使用该杂环化合物的有机电子装置,具体而言,所述杂环化合物可以适用于有机半导体装置、钙钛矿太阳能电池装置以及有机电发光装置(有机EL装置)。此外,本发明的杂环化合物在应用于钙钛矿太阳能电池装置和有机EL装置,并作为电洞传输层(HTL)或电子传输层(ETL)材料时,具有优异的性能。
背景技术
有机电子材料开发时间已有数十年之久。近来有机电子材料因其在面板、可弯曲屏幕、固态照明、太阳能储存等的潜在应用,引起了产业实务运用的极大关注,并广泛地应用于有机电子装置,如:有机薄膜晶体管(OTFT)、有机EL装置、有机光伏装置(OPV)、钙钛矿太阳能电池装置等。有机EL为发光二极管(LED),其发光层是一种能够通过电流发光的有机化合物薄膜。此有机化合物薄膜发光层介于两个电极之间。有机EL装置有着诸多优点,如:可以自行发射,拥有更宽的视角、更快的反应速度和高发光度。此外,有机EL装置能够通过更简单的制造方式,就能达到与液晶屏幕相同的清晰显示度,因此有机EL装置是目前显示工业中的首选装置,并已投入商业化阶段。有机光伏装置(OPV)包括基板、第一电极、第二电极和光电转换层。第一电极设置于基板上,第二电极设置于第一电极上,光电转换层配置于第一电极和第二电极间。此装置单元通过吸收光而产生电荷。OPV因成本低、容易准备、具有大面积能力,而被认为拥有绿色能源技术的高成长趋势,OPV转换效率已达到可实际应用的程度。有机薄膜晶体管(OTFT)在具有绝缘表面的基板上,至少包含有闸极、与闸极形成的闸极绝缘膜、与闸极绝缘膜接触所形成的有机半导体膜以及与有机半导体膜接触所形成的至少一对汲极与源极,产生电极通过闸极讯号而将载子注入,并将载子导引至有机半导体膜内。OTFT因其具有低成本、灵活度、低温处理、和大面积能力的优点,已成为有机电子的热点。其性能已和非晶硅薄膜晶体管的性能相当。
近来,太阳能电池对于人们的重要性持续增加,用以作为化石燃料的替代性能源。然而,现今太阳能电池多以硅基为主流,成本相当之高。因此,各种较为廉价的太阳能电池正在研发中,其中洛桑联邦理工学院格雷策尔(Graetzel)等人发表的染料敏化型太阳能电池,受到各方的高度期待(日本专利号2664194;《自然期刊》 Nature,353(1991)737;《美国化学会志》J.Am.Chem.Soc.,115(1993)6382)。
此外,桐荫横浜大学宫坂(Miyasaka)等人于《美国化学会志》(J.Am.Chem.Soc.,131(2009)6050)中发表了能吸光并产生电力的钙钛矿太阳能电池。钙钛矿太阳能电池所使用的钙钛矿结构化合物,是通过混合卤代甲胺和卤化铅制成的。钙钛矿结构化合物对于可见光能呈现强效的吸收作用。《科学期刊》(Science 338(2012)643)中,写道钙钛矿太阳能电池可提升光电转换效率,但其中发表的钙钛矿太阳能电池,并不能取得令人满意的光电转换效率。因此,目前的任务是需要寻找具有更高的光电转换效率的钙钛矿太阳能电池。
有机半导体装置的性能主要以半导体材料的电荷载子迁移率和电流开/关比为基础。理想的半导体在断开状态下,应能具有低导电性和高电荷载子迁移率(>1× 10-3cm2V- 1s-1)。此外,重要的是,若半导体被氧化会造成装置性能的降低,半导体材料应当具有相对稳定的抗氧化作用,即具有高的电离电位。另外,半导体材料也应具有良好的加工能力,特别是对于大规模生产薄层和所需图案;并具有高稳定性、膜均匀性和完整性。
然而,在有机电子装置中仍存在许多技术性问题,如:材料不稳定、功率效率低、寿命较短等;这些因素都阻碍了有机电子装置的商业化。一种良好的有机电子材料对于有机电子装置而言,应具有良好的热稳定性、与更有效率和较长半衰期。
本发明的杂环化合物的现有技术包含:US8313672B2、JP 2005-156822A1、《有机化学通讯》(Org.Lett.)第6卷2号,273-276(2004),《无机化学》(Inorg.Chem.)2011, 50,471-478。
发明内容
本发明提供了一种杂环化合物,可作为电洞传输层(HTL)、电子传输层(ETL)、或有机电子装置(有机EL、OPV、钙钛矿太阳能电池或OTFT)的主动层,本发明的杂环化合物能克服传统材料的缺点,具有较高的稳定性、较长的半衰期、较低的功耗,以及产业利用的经济优势。
本发明的杂环化合物由下式(I)表示,适用于有机半导体装置、钙钛矿太阳能电池装置和有机电发光装置(有机EL装置)。特别地,本发明使用的杂环化合物作为电洞传输层(HTL)、或钙钛矿太阳能电池装置与有机EL装置的电子传输层(ETL),能显示出优异的性能。
其中,X1至X4独立代表硫或硒原子;Ar1至Ar6独立地选自氢原子、卤化物、卤原子、-CN、-NC、-NCS、-SCN、-NH2、-OH、-NO2、-CF3、-NC、取代或未取代的碳原子数为1~30的烷基、取代或未取代的碳原子数为6~30的芳基、取代或未取代的碳原子数为3~30的杂芳基、取代或未取代的碳原子数为6~30的芳烷基、取代或未取代的碳原子数为6~30的烷氧基、取代或未取代的碳原子数为6~30 的烯基,取代或未取代的碳原子数为6~30的烷基胺。
综上所述,本发明的化合物及装置不但在空间型态上确属创新,并能较现有技术增进上述多项功效,应已充分符合新颖性及进步性的法定发明专利要件,爰依法提出申请,恳请贵局核准本件发明专利申请案,以励发明,至感德便。
附图说明
图1为本发明的OTFT装置示意图;
图2为本发明的钙钛矿太阳能电池装置示意图。
[符号说明]
1 基板
2 闸极层
3 绝缘层
4 有机半导体层
5 汲极层
6 源极层
7 ITO玻璃
8 电洞注入层
9 电洞传输层
10 钙钛矿层
11 电子接受层
12 电子传输层
13 金属层
具体实施方法
为方便审查员了解本发明的技术特征、技术优点及其所能达到的技术效果,下面结合具体实施例和附图来进一步描述本发明,本发明的优点和特点将会随着描述而更为清楚。但这些实施例仅是范例性的,并不对本发明的范围构成任何限制。本领域技术人员应该理解的是,在不偏离本发明的精神和范围下可以对本发明技术方案的细节和形式进行修改或替换,但这些修改和替换均落入本发明的保护范围内。
本发明所提供的杂环化合物以及使用该杂环化合物的有机电子装置将于下方提供生产、结构、装置和部分较佳实施例的详细说明,来让本发明能彻底为人所了解。一方面,本发明的应用不限于本领域技术人员熟悉的具体细节。另一方面,众人周知的共同要素与程序并未详细说明,以避免对本发明构成不必要的限制。应当指出的是,除已明确说明的实施例外,本发明也能广泛运用于其它实施例的施行,且这些实施例不对本发明的权利要求范围构成任何限制。
于本发明的实施例中,公开了可用于有机EL装置的有机电子材料、OPV装置、钙钛矿太阳能电池装置或OTFT器件。所述有机电子材料,由下式(I)表示:
其中,X1至X4独立代表硫或硒原子,Ar1至Ar6独立地选自氢原子、卤化物、卤原子、-CN、-NC、-NCS、-SCN、-NH2、-OH、-NO2、-CF3、-NC、取代或未取代的碳原子数为1~30的烷基、取代或未取代的碳原子数为6~30的芳基、取代或未取代的碳原子数为3~30的杂芳基、取代或未取代的碳原子数为6~30的芳烷基、取代或未取代的碳原子数为6~30的烷氧基、取代或未取代的碳原子数为6~30 的烯基,取代或未取代的碳原子数为6~30的烷基胺。
优选的,所述Ar1至Ar6独立地选自下列取代基:
其中,R1和R2代表烷基或芳基。
优选的,在实施例中,所述杂环化合物如下所示:
本发明提供一种有机电子装置,包含本发明所述的杂环化合物。优选的,所述有机电子装置为有机半导体装置、钙钛矿太阳能电池装置或有机电发光装置(有机 EL装置)。
本发明的有机半导体电子装置,包括一闸极、一金属氧化物层、一黏着层、一汲极、一源极及一主动层。优选的,所述主动层包含本发明所述的杂环化合物;优选的,所述闸极由硅、掺杂硅或铝制成;优选的,所述金属氧化物层由氧化硅或氧化铝制成;优选的,所述黏着层由钛、钨或铬制成;优选的,所述汲极由金或白金制成;优选的,所述源极包含一金层或一白金层。
本发明的有机EL装置的电洞传输层或电洞注入层包含本发明所述的杂环化合物。
本发明的有机EL装置的电子传输层包含本发明所述的杂环化合物。
本发明的钙钛矿太阳能电池装置的电洞传输层包含本发明所述的杂环化合物。
本发明的钙钛矿太阳能电池装置的电子传输层包含本发明所述的杂环化合物。
本发明的有机太阳能电池装置的电洞传输层包含本发明所述的杂环化合物。
本发明的有机太阳能电池装置的电子传输层包含本发明所述的杂环化合物。
下面通过具体实施例对本发明进行详细说明。实施例1~6为本发明的杂环化合物的制备实施例。实施例7为本发明的有机TFT装置和I-V-B的制造实施例和有机EL装置的测试报告。实施例8为本发明的钙钛矿太阳能电池装置的制造实施例和I-V与能量转换效率的测试报告。
实施例1化合物1的合成
1、中间体A的合成
将25克(67.6mmol)的乙基5,6-二溴噻吩并[3,2-b]噻吩-2-甲酸乙酯(ethyl 5,6-dibromothieno[3,2-b]thiophene-2-carboxylate)(该化合物按照《无机化学》(Inorg.Chem.)2009,50,471-478的方法合成)、13.0克(101.3mmol)的噻吩-3-基硼酸 (thiophen-3-ylboronic acid)、0.8克(0.067mmol)的四(三苯基膦)钯(Pd(PPh3)4)、101ml 的 2M碳酸钠(Na2CO3)、300ml的甲苯(toluene)和100ml的乙醇(EtOH)混合脱气并置于氮气下,然后在100℃加热12小时。反应完成后,将混合物冷却至室温。有机层用二氯甲烷(dichloromethane)和水萃取,然后用无水硫酸镁(anhydrous magnesium sulfate)干燥,除去溶剂。残余物通过硅胶柱色谱纯化,得到产物(16.8克,66%)。
2、中间体B的合成
于已脱气并充满氮气的三口烧瓶内加入1.6克(4.4mmol)的中间体A、0.95克(6.7mmol)的三氟化硼乙醚(boron trifluoride diethyl etherate)和1.6克(7.0mmol)的二氯二氰基苯醌(D.D.Q.),混合并溶于425ml的无水二氯甲烷(anhydrousdichloromethane) 中,于室温下搅拌24小时。然后加入0.03克(0.44mmol)的锌(Zinc)和850ml的甲醇 (MeOH),于室温下搅拌24小时。于混合物中加入水和二氯甲烷(dichloromethane) 以终止反应。分离有机层并以真空的方式除去溶剂。残余物通过硅胶柱色谱纯化,得到产物(0.7克,42%)。
3、中间体C的合成
在-78℃的氮气环境下,将74.8mmol的二异丙基胺(LDA)的四氢呋喃(THF)溶液滴加到140mL含有7.0克(18.7mmol)的中间体B的THF溶液中。将混合物的温度维持1小时,并于-78℃下搅拌1小时,之后在-78℃下向混合物中滴加30.4克 (93mmol)1,2-二溴四氯乙烷(1,2-dibromotetrachloroethane),然后将混合物温热至室温并搅拌过夜。于混合物中加入水以中止反应。分离有机层并以真空的方式除去溶剂。残余物通过硅胶柱色谱纯化,得到产物(5.9克,60%)。
4、中间体D的合成
将5.9克(11.2mmol)的中间体C、22.4ml的1M氢氧化锂(LiOH)(水溶液)和60ml 的四氢呋喃(THF)进行混合。将混合物在60℃下加热2小时。反应完成后,将混合物冷却至室温。有机层用乙酸乙酯(ethyl acetate)和水萃取,然后用无水硫酸镁(anhydrousmagnesium sulfate)干燥,除去溶剂。残余物通过硅胶柱色谱纯化,得到产物(5.3克,95%)。
5、中间体E的合成
将5.3克(10.6mmol)的中间体D、0.4克(6.3mmol)的铜(Copper)和40ml的喹啉(Quinoline)混合,边搅拌边加热回流2小时,直至反应完成。将反应混合物冷却,用二氯甲烷(dichloromethane)和水萃取,然后用无水硫酸镁(anhydrous magnesium sulfate)干燥除去溶剂,得到残余物(2.6克,50%)。
6、中间体F的合成
在-78℃的氮气环境下,将含有10.6mmol二异丙基胺(LDA)的四氢呋喃(THF) 溶液滴加到50mL的含有2.6克(5.3mmol)的中间体E的THF溶液中。将混合物的温度维持1小时,并于-78℃下搅拌1小时,然后在-78℃下将4.3克(13.3mmol)的1,2- 二溴四氯乙烷(1,2-dibromotetrachloroethane)滴加到混合物中,然后将混合物温热至室温并搅拌过夜。于混合物中加入水以终止反应。分离有机层并以真空的方式除去溶剂。残余物通过硅胶柱色谱纯化,得到产物(2克,72%)。
7、中间体G的合成
将5克(10.9mmol)的中间体E、6.7克(26.2mmol)的双(频哪醇)二硼 (bis(pinacolato)diboron)、0.12克(0.11mmol)的四(三苯基膦)钯(Pd(PPh3)4)、3.2克(32.7mmol)的乙酸钾(potassium acetate)、和75ml的1,4-二恶烷(1,4-dioxane)混合脱气并置于氮气下,在90℃下加热16小时。反应完成后,将混合物冷却至室温。分离有机相,用乙酸乙酯(ethyl acetate)和水萃取,然后用无水硫酸镁(anhydrous magnesium sulfate)干燥后,真空除去溶剂。残余物通过硅胶柱色谱纯化,得到产物 (4.9克,81%)。
8、化合物1的合成
将2克(4.4mmol)的中间体E、2.9克(9.7mmol)的三甲基(噻吩并[3,2-b]噻吩-2-基) 锡烷(trimethyl(thieno[3,2-b]thiophen-2-yl)stannane)、0.5克(0.44mmol)的四(三苯基膦) 钯(Pd(PPh3)4)和60ml的甲苯(toluene)混合脱气并置于氮气下,然后在100℃下加热 12小时。反应完成后,将混合物冷却至室温。有机层用二氯甲烷(dichloromethane)和水萃取,然后用无水硫酸镁(anhydrous magnesium sulfate)干燥,真空除去溶剂。残余物通过硅胶柱色谱纯化,得到产物(1.7克,66%)。MS(m/z,,EI+):578.3。
实施例2化合物2的合成
将1克(1.8mmol)的中间体F、1.8克(6.0mmol)的三甲基(噻吩并[3,2-b]噻吩-2-基) 锡烷(trimethyl(thieno[3,2-b]thiophen-2-yl)stannane)、0.21克(0.18mmol)的四(三苯基膦) 钯(Pd(PPh3)4)和30ml的甲苯(toluene)混合脱气并置于氮气下,然后在100℃下加热 12小时。反应完成后,将混合物冷却至室温。有机层用二氯甲烷(dichloromethane)和水萃取,然后用无水硫酸镁(anhydrous magnesium sulfate)干燥,真空除去溶剂。残余物通过硅胶柱色谱纯化,得到产物(0.7克,53%)。MS(m/z,,EI+):716.8。
实施例3化合物3的合成
将2克(4.4mmol)的中间体E、1.6克(9.7mmol)的二苯胺(diphenylamine)、0.5克(0.44mmol)的四(三苯基膦)钯(Pd(PPh3)4)、0.06克(0.22mmol)的丁基鏻四氟硼酸盐(butylphosphoniumtetrafluoroborate)、1.26克(13.2mmol)的叔丁醇钠(sodium tert-butoxide)和60ml的甲苯(toluene)混合脱气并置于氮气下,然后在110℃下加热12小时。反应完成后,将混合物冷却至室温。有机层用二氯甲烷(dichloromethane) 和水萃取,然后用无水硫酸镁(anhydrous magnesium sulfate)干燥,除去溶剂。残余物通过硅胶柱色谱纯化,得到产物(1.3克,48%)。MS(m/z,,EI+):637.0。
实施例4化合物4的合成
将2克(4.4mmol)的中间体E、2.2克(9.7mmol)的双(4-甲氧基苯基)胺 (bis(4-methoxyphenyl)amine)、0.5克(0.44mmol)的四(三苯基膦)钯(Pd(PPh3)4)、0.06 克(0.22mmol)的三叔丁基鏻四氟硼酸盐(tri-tert-butylphosphoniumtetrafluoroborate)、1.26g(13.2mmol)的叔丁醇钠(sodium tert-butoxide)和60ml的甲苯(toluene)混合脱气并置于氮气下,然后在110℃下加热12小时。反应完成后,将混合物冷却至室温。有机层用二氯甲烷(dichloromethane)和水萃取,然后用无水硫酸镁(anhydrous magnesium sulfate)干燥,除去溶剂。残余物通过硅胶柱色谱纯化,得到产物(1.3克, 40%)。MS(m/z,,EI+):757.1。
实施例5化合物5的合成
将1克(1.8mmol)的中间体G、1.44克(5.4mmol)的2-氯-4,6-二苯基-1,3,5-三嗪(2-chloro-4,6-diphenyl-1,3,5-triazine)、0.02克(0.02mmol)的四(三苯基膦)钯 (Pd(PPh3)4)、2.7ml的2M碳酸钠(Na2CO3)、20ml的甲苯(toluene)和5ml的乙醇(EtOH) 混合脱气并置于氮气下,然后在100℃下加热12小时。反应完成后,将混合物冷却至室温。有机层用二氯甲烷(dichloromethane)和水萃取,然后用无水硫酸镁(anhydrous magnesium sulfate)干燥,真空除去溶剂。残余物通过硅胶柱色谱纯化,得到产物(0.6 克,45%)。MS(m/z,,EI+):764.3。
实施例6化合物6的合成
将2克(4.4mmol)的中间体F、6.3克(14.5mmol)的2-氯-4,6-二苯基-1,3,5-三嗪(2-chloro-4,6-diphenyl-1,3,5-triazine)、0.05克(0.04mmol)的四(三苯基膦)钯 (Pd(PPh3)4)、8.8ml的2M碳酸钠(Na2CO3)、40ml的甲苯(toluene)和10ml的乙醇(EtOH) 混合脱气并置于氮气下,然后在100℃下加热12小时。反应完成后,将混合物冷却至室温。有机层用二氯甲烷(dichloromethane)和水萃取,然后用无水硫酸镁(anhydrous magnesiumsulfate)干燥,除去溶剂。残余物通过硅胶柱色谱纯化,得到产物(3.5克, 66%)。MS(m/z,,EI+):1223.6。
生产有机电子装置的一般性方法
将具有9~12奥姆/平方米的电阻且厚度为120~160nm的ITO涂层玻璃(下称ITO基板)于超音波浴(如:洗涤剂、去离子水)中清洗数次。于有机层蒸汽沉积前,将清洁后的ITO基板通过紫外线和臭氧进一步进行处理。ITO基板的所有预处理疗程,均于无尘室进行(100级)。
通过于高真空单元的气相沉积作用,将有机小分子层(10-7托)依次沉积至ITO 基板上,如:电阻加热的石英舟(借助石英晶体监测器精确监测或设定各层厚度和气相沉积速率(0.1~0.3nm/秒));或也能由个别层组成一种以上的化合物,即加入掺杂剂材料的主体材料(通过两个或更多来源的共蒸镀实现)。
实施例7本发明的有机TFT装置和I-V-B的制造及有机EL装置的测试报告
本发明的有机薄膜晶体管(OTFT)装置的基板,为具有热成长的250nm二氧化硅的磷掺杂硅(p+-doped Si)。于二氧化硅闸极氧化物上以溶胶-凝胶涂覆上聚甲基丙烯酸甲酯(Polymethylmethacrylate)。薄膜的沉积参数及其作为表面修饰层的对象和有机半导体层沉积程序,会在其它地方进行说明。之后,有机半导体层会旋转涂布、或沉积于聚甲基丙烯酸甲酯薄膜上。然后通过热蒸镀让超薄氟化锂层(LiF)沉积至有机半导体层。其中,被修饰的有机半导体层的氟化锂层的厚度范围为0.1至1nm。最后,通过屏蔽将60nm厚的铝,蒸镀到被修饰的有机半导体层上,形成源/汲极。使用石英晶体监视器来量测膜厚。本装置具有一般OTFT装置的信道宽度为20公分、长度为10um的输出特征。
使用与上述一般方法类似的方法,制作具有以下装置结构的OTFT装置(参见图1),其依序设有基板1、闸极层2、绝缘层3、有机半导体层4、汲极层5以及源极层6。其中,有机半导体层4可为实施例1至6的化合物以及其它类似化合物如:并五苯(pentacene)和6,13-双(三异丙基甲硅烷基乙炔基)并五苯(6,13-bis(tri isopropylsilylethynyl)pentacene,TIPS),这些化合物被旋抹涂布或沉积于装置结构上,来各自形成薄膜。
使用HP 4156C和Keithley 4200半导体参数分析仪,在具有氮气环境的手套箱中进行装置电气测量。电容电压(C-V)测量用Agilent E4980A精密阻抗分析仪进行。
现有技术中用于生产标准OTFT装置的、与本发明作为比较的OTFT材料的化学结构式如下:
不同OTFT材料的OTFT装置的场效载子移动率、和开/关电流比数据如表1所示。
表1
由此可见,本发明中具有式(I)的杂环化合物作为OTFT装置的有机薄膜材料可以显示出较现有技术更好的性能。
实施例8本发明的钙钛矿太阳能电池装置的制造及I-V与能量转换效率的测试报告
使用与上述一般方法类似的方法,制作具有以下装置结构的钙钛矿太阳能电池装置(参见图2),其依序设有ITO玻璃7、电洞注入层8、电洞传输层9、钙钛矿层10、电子接受层11以及电子传输层12,ITO/二氧乙基噻吩:聚苯乙烯磺酸(PEDOT: PSS)/实施例1~实施例6的化合物(30nm)/钙钛矿层:CH3NH3PbI3/PCBM/ BCP(10nm)/Al(100nm)。
电洞注入层8(HI):将PEDOT:PSS(AI4083)旋涂1分钟(4000rpm)至ITO玻璃 7表面,然后在130℃退火30分钟。
电洞传输层9:实施例1~实施例6的化合物透过热蒸镀沉积。
钙钛矿层10:将碘化铅(PbI2)(比重40%)(99%,Alfa Aesar)溶于无水二甲基亚砜 (Dimethyl sulfoxide,DMSO)中,并于70℃的热板上搅拌过夜。将碘化铅的热溶液以4000rpm(40秒)旋抹涂布于PEDOT:PSS膜上,并将样品于70℃下保持于热板上 30分钟。
将CH3NH3PbI3(比重2%)溶于无水2-丙酮(2-proponal)中,并于70℃的热板上搅拌过夜。将CH3NH3PbI3的热溶液以5000rpm(40秒),旋抹涂布到碘化铅膜,并将样品在100℃下保持在热板上120分钟。
电子接受层11(EA):在中的[6,6]-苯基-C61-丁酸甲酯([6,6]-phenyl-C61-butyric acid methyl ester,PC61BM)(85nm)溶于二氯苯(CB)的溶液(20mg/mL),旋转(6000rpm,60秒)至钙钛矿层10上,然后在90℃退火30分钟。
电子传输层12(ET)和阴极:通过于真空屏蔽下以2,9-二甲基-4,7-二苯基-1,10-菲咯啉(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)(BCP)(10nm)和铝电极(100nm) 的连续热蒸镀,来完成装置结构。
[6,6]-苯基-C61-丁酸甲酯([6,6]-phenyl-C61-butyric acid methyl ester,PC61BM)用于电子受体材料。2,9-二甲基-4,7-二苯基-1,10-菲咯啉 (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)(BCP)作为电子传输材料。
现有技术中用于制备准标钙钛矿装置对照电洞传输层的、与本发明作为比较的有机材料为聚[N,N'-双(4-丁基苯基)-N,N'-双(苯基)-联苯胺] (poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)-benzidine],Poly-TPD),其化学结构如下:
以太阳能仿真器100mW/cm2(1SUN光照设定)的照度,照射于钙钛矿太阳能电池上。当电流电压特性稳定后,测定电流-电压特性,来求出转换效率以作为初始转换效率。将加热测试后的转换效率与初始转换效率的比率进行计算,以求出其保留率。
钙钛矿装置测试报告的I-V数据(1SUN照度设定)如表2所示。
表2
由此可见,本发明的式(I)化合物相较于现有技术的钙钛矿太阳能电池用于电洞传输材料的性能更好。
本发明提供的杂环化合物由下式(I)表示,适用于有机半导体装置、钙钛矿太阳能电池装置、和有机电发光装置(有机EL装置)。特别地,本发明使用的杂环化合物作为电洞传输层(HTL)、或钙钛矿太阳能电池装置与有机EL装置的电子传输层 (ETL),能显示出优异的性能。
其中,X1至X4独立代表硫或硒原子;Ar1至Ar6独立地选自氢原子、卤化物、卤原子、-CN、-NC、-NCS、-SCN、-NH2、-OH、-NO2、-CF3、-NC、取代或未取代的碳原子数为1~30的烷基、取代或未取代的碳原子数为6~30的芳基、取代或未取代的碳原子数为3~30的杂芳基、取代或未取代的碳原子数为6~30的芳烷基、取代或未取代的碳原子数为6~30的烷氧基、取代或未取代的碳原子数为6~30 的烯基,取代或未取代的碳原子数为6~30的烷基胺。
综上所述,本发明的化合物及装置不仅于技术思想上确属创新,并具备现有技术所不及的上述多项功效,已充分符合新颖性及进步性的法定发明专利要件,爰依法提出申请。
Claims (18)
1.一种杂环化合物,其特征在于,由下式(I)表示:
其中,X1至X4独立代表硫或硒原子;Ar1至Ar6独立地选自氢原子、卤化物、-CN、-NC、-NCS、-SCN、-NH2、-OH、-NO2、-CF3、-NC、取代或未取代的碳原子数为1~30的烷基、取代或未取代的碳原子数为6~30的芳基、取代或未取代的碳原子数为3~30的杂芳基、取代或未取代的碳原子数为6~30的芳烷基、取代或未取代的碳原子数为6~30的烷氧基、取代或未取代的碳原子数为6~30的烯基,取代或未取代的碳原子数为6~30的烷基胺。
2.如权利要求1所述的杂环化合物,其特征在于,所述Ar1至Ar6独立地选自下列取代基:
其中,R1和R2代表烷基或芳基。
3.如权利要求1所述的杂环化合物,其特征在于,所述杂环化合物由下式之一表示:
4.一种有机电子装置,其特征在于,所述有机电子装置包含如权利要求1所述的杂环化合物。
5.如权利要求4所述的有机电子装置,其特征在于,所述装置为有机半导体装置、钙钛矿太阳能电池装置、有机太阳能电池装置或有机电发光装置(有机EL装置)。
6.一种有机半导体电子装置,其特征在于,包括一闸极、一金属氧化物层、一黏着层、一汲极、一源极及一主动层。
7.如权利要求6所述的有机半导体电子装置,其特征在于,所述主动层包含如权利要求1所述的杂环化合物。
8.如权利要求6所述的有机半导体电子装置,其特征在于,所述闸极由硅、掺杂硅或铝制成。
9.如权利要求6所述的有机半导体电子装置,其特征在于,所述金属氧化物层由氧化硅或氧化铝制成。
10.如权利要求6所述的有机半导体电子装置,其特征在于,所述黏着层由钛、钨或铬制成。
11.如权利要求6所述的有机半导体电子装置,其特征在于,所述汲极由金或白金制成。
12.如权利要求6所述的有机半导体电子装置,其特征在于,所述源极包含一金层或一白金层。
13.一种有机EL装置,其特征在于,所述装置的电洞传输层或电洞注入层包含如权利要求1所述的杂环化合物。
14.一种有机EL装置,其特征在于,所述装置的电子传输层包含如权利要求1所述的杂环化合物。
15.一种钙钛矿太阳能电池装置,其特征在于,所述装置的电洞传输层包含如权利要求1所述的杂环化合物。
16.一种钙钛矿太阳能电池装置,其特征在于,所述装置的电子传输层包含如权利要求1所述的杂环化合物。
17.一种有机太阳能电池装置,其特征在于,所述装置的电洞传输层包含如权利要求1所述的杂环化合物。
18.一种有机太阳能电池装置,其特征在于,所述装置的电子传输层包含如权利要求1所述的杂环化合物。
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US15/442,713 | 2017-02-27 |
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CN108727405B (zh) * | 2018-07-27 | 2022-02-01 | 武汉天马微电子有限公司 | 一种芳杂环化合物以及有机发光显示装置 |
US11380848B2 (en) * | 2019-01-16 | 2022-07-05 | Luminescence Technology Corp. | Organic compound and organic electroluminescence device using the same |
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