CN101279969A - 一种有机电致发光材料及其应用 - Google Patents

一种有机电致发光材料及其应用 Download PDF

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CN101279969A
CN101279969A CNA2008100066249A CN200810006624A CN101279969A CN 101279969 A CN101279969 A CN 101279969A CN A2008100066249 A CNA2008100066249 A CN A2008100066249A CN 200810006624 A CN200810006624 A CN 200810006624A CN 101279969 A CN101279969 A CN 101279969A
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thia
compound
group
amido
phenyl
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CN101279969B (zh
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邱勇
陈瀚
李银奎
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Tsinghua University
Beijing Visionox Technology Co Ltd
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Tsinghua University
Beijing Visionox Technology Co Ltd
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Abstract

本发明涉及一种新型化合物和包含该化合物的有机电致发光器件。该化合物的结构通式如下所示，X，Y分别独立选自含一至三个杂原子的五元或六元的芳香环或芳香稠环，或选自亚甲基，且不同时为亚甲基；Ar1，Ar2分别独立选自氢原子、氟原子、羰基、腈基、酰氧基、亚乙烯基、烷基、烷氧基、烷基氨基、烷硫基、芳基或取代芳基、稠环芳基或芳胺基团。本发明的材料可优先用作发光体，同时还可用作电子传输、空穴阻挡材料，利用本发明的材料制备的电致发光器件表现出高色纯度、高亮度、高效率的优越性能。

Description

一种有机电致发光材料及其应用
技术领域
本发明中涉及一种新型化合物，及其在电致发光器件中的应用，属于有机电致发光显示技术领域。
背景技术
发光二极体是一种很重要的光电材料，普遍应用于电子，光电，民生等各项产品。电致发光现象最早是在1936年，Destriau等人以ZnS粉末为发光材料观察到的，现比较常用的是无机的磷砷化镓红色发光二极体，但是由无机发光二极体以不同发光材料配合不同的单晶生产技术，所以无法制造高解析度显示器，与之相比有机分子加工性能好，可以在任何机板上成膜，选择范围款，很多发光材料都有很高的发光效率，并且可以通过结构设计来调控分子的热性能，机械性能，发光性能，电导性能等，使材料有很大的改善空间。
发光材料是有机电致发光器件中很重要的一类材料，一般发光材料要具有以下特点：
(1)在固态或者溶液中在可见光区要有较高的荧光量子效率；
(2)具有较好的电导率，呈现良好的半导体特性；
(3)具有良好的成膜性能，在几百纳米薄膜内基本无针孔；
(4)稳定性强，一般具有良好的机械加工性能。
一般具有较大共轭面的稠环芳香化合物具有较高的荧光量子效率和较长的荧光发射寿命所以常用来作为发光材料的发光中心，但是单纯的稠环芳香烃存在容易结晶，并且传输能力比较差，发光波长比较单调等问题，而通过一些具有吸电子或者推电子取代基的引入能过改善电导性能，成膜性能以及发光波长。
发明内容
本发明的目的是提出一种新型电致发光材料，克服目前常用的材料所存在的上述问题，提高材料的色纯度、荧光量子效率和电致发光效率，改善材料成膜性能，并保证材料容易合成生产。
杂环化合物具有良好的推电子性能或吸电子性能，并且具有芳香性，可以扩展分子的共轭面，提高发光效率，除此之外，杂原子氮，硫，氧还具有孤对电子，可以与发光中心的芳香基团发生p-π共轭，从而使孤对电子游离于整个分子平面，有利于改善分子的发光性能和电导性能，呈现出p型半导体或n型半导体的性质。
在长期研究后，本发明人发现了特定结构的二萘乙烯分子，具有良好的热稳定性能、高效率的蓝色发光性能、简便的合成方法和提纯步骤。随后将其运用到器件中，发现当改变取代基团的种类和位置时，可以获得发光波长不同的电致发光器件。根据共轭理论，其中4，11位最优位点，当这些位点被杂环基团取代时，器件的发光波长会发生改变，发光效率得到了提高，并且具有半导体类似的传输性能，所得到的器件具有很高的色纯度和效率，可以应用于全彩色显示器的制造生产中。因此本发明采取了在发光中心二萘乙烯的6位和6’为分别或同时接入含一至三个杂原子的杂环，并在杂环的其他位置接入推电基团或者吸电基团来对分子的发光波长和机械性能进行调解。
本发明提出一种新型有机电致发光材料，其结构通式如下所示：
Figure A20081000662400141
X，Y分别独立选自含一至三个杂原子的C4-20的五元或六元的芳香环，或选自含有一至三个杂原子的C6-20 的芳香稠环，或选自亚甲基，且X，Y不同时为亚甲基；
Ar1，Ar2分别独立选自氢原子、氟原子、羰基、腈基、酰氧基、亚乙烯基、C1-30的烷基或取代烷基、C1-30的烷氧基或取代的烷氧基、C2-30的烷基氨基或取代的烷基氨基、C1-30的烷硫基或取代烷硫基、C6-20的芳基或取代芳基、C6-20的稠环芳基或C6-30的芳胺基团。上述通式中，优选的X，Y分别独立选自吡咯基、噻吩基、呋喃基、吡啶基、喹啉基、异喹啉基、咔唑基、菲啶基、苯并噻吩基、苯并呋喃、吡唑基、咪唑基、呋咱基、硫杂吡咯基、氮杂呋喃基、氮杂噻吩基、硫杂嘧啶基、硫杂吡啶基、硫杂喹啉基、硫杂异喹啉基、硫杂哒嗪基、硫杂嘧啶基、硫杂吡嗪基、硫杂哒嗪基、噁二唑、嘧啶基、吡嗪基、氮杂苯并噻吩基、硫杂吲哚、硫杂异吲哚、硫杂吲唑、吡唑并喹啉、亚甲基X，Y相等或不等，X，Y不同时为亚甲基；
优选的Ar1，Ar2分别独立选自氢原子、甲基、乙基、异丙基、叔丁基、羰基、腈基、酰氧基、亚乙烯基、甲氧基、乙氧基、异丙氧基、叔丁基氧基、N，N-二甲基胺基、N，N-二乙基胺基、甲硫基、乙硫基、异丙基硫基、叔丁基硫基、氟原子、苯基、联苯基、萘基、蒽基、芘基、芴基、并四苯基、N，N-二苯基胺基、N，N-二(α-萘基)胺基、N，N-二(β-萘基)胺基、N-苯基-N-(α-萘基)胺基、N-苯基-N-(β-萘基)胺基、N-甲基-N-苯基胺基、咔唑基、对咔唑基苯基、对N’N-二苯基氨基苯基。
一种有机电致发光器件，包括第一电极和第二电极，以及位于两电极之间的有机功能层，其特征在于，有机功能层中的至少一层包含具有下列结构式的化合物：
Figure A20081000662400151
X，Y分别独立选自含一至三个杂原子的C4-20的五元或六元的芳香环，或选自含有一至三个杂原子的C6-20 的芳香稠环，或选自亚甲基，且X，Y不同时为亚甲基；
Ar1，Ar2分别独立选自氢原子、氟原子、羰基、腈基、酰氧基、亚乙烯基、C1-30的烷基或取代烷基、C1-30的烷氧基或取代的烷氧基、C2-30的烷基氨基或取代的烷基氨基、C1-30的烷硫基或取代烷硫基、C6-20的芳基或取代芳基、C6-20的稠环芳基或C6-30的芳胺基团。
本发明的化合物通式中，优选的X、Y、Ar1、Ar2的分子结构式如下：
Figure A20081000662400152
Figure A20081000662400161
Figure A20081000662400171
为了更清楚叙述本发明内容，下面具体叙述但不限于本发明涉及到的分子结构：
Figure A20081000662400181
Figure A20081000662400191
Figure A20081000662400201
Figure A20081000662400211
Figure A20081000662400221
Figure A20081000662400231
Figure A20081000662400241
本发明的材料具有以下优点：
本发明中的这类二萘乙烯分子，是一类全新的可用于OLED的电致发光材料。该材料可以用作有机电致发光器件中的发光层主体材料或者作为发光层中掺杂的染料。该材料还可以用作有机电致发光器件中的电子传输和空穴阻挡层。利用本发明的电致发光材料制备的有机电致发光器件可表现出高纯度、高亮度、高效率的优越性能。
附图说明
图1化合物1制备的OLED2的电致光谱
图2化合物1制备的OLED2的电流效率图
图3化合物32的渡越时间测定的迁移率结果
具体实施方式
下面是本发明的化合物的合成实施例：
实施例一  化合物1：
反应式：
Figure A20081000662400251
过程：
在配有磁力搅拌器，冷凝回流装置及氮气保护装置的500ml三口烧瓶中，加入2-溴-5-碘噻吩28.9克(100mmol)，苯硼酸15.3克(125mmol)，醋酸钯0.22克(1mmol)，三苯基膦0.53克(2mmol)，碳酸钾34.0克(240mmol)，用水泵减压进行真空→氮气→真空的置换，反复进行5次，然后加入甲苯250ml，再次用水泵进行真空→氮气→真空的置换，反复进行5次。加热回流，反应24小时。停止加热，冷却到室温。
将反应液倾入15cm高硅胶柱中，减压抽滤，以石油醚冲洗，收集滤液，旋去溶剂，得2-溴-5-苯基噻吩16.5g。
在配有磁力搅拌器及氮气保护装置的250ml三口烧瓶中，加入2-溴-5-苯基噻吩14.3g(50mmol)，再加入100ml无水THF，搅拌，降温至-78℃。向反应器中滴入0.06mol丁基锂，反应2h，再滴入8.5ml硼酸三甲酯。反应搅拌过夜。加入10ml3M盐酸水解，分液，取有机相。浓缩产物，加入石油醚重结晶。得到5-苯基噻吩-2-硼酸8.9g。
在配有磁力搅拌器，冷凝回流装置及氮气保护装置的100ml三口烧瓶中，加入5-苯基噻吩-2-硼酸5.8克(25mmol)，6-溴-2-萘醛4.7克(20mmol)，醋酸钯0.044克(0.2mmol)，三苯基膦0.106克(0.4mmol)，碳酸钾6.9克(50mmol)，用水泵减压进行真空→氮气→真空的置换，反复进行5次，然后加入甲苯50ml，再次用水泵进行真空→氮气→真空的置换，反复进行5次。加热回流，反应24小时。停止加热，冷却到室温。
将反应液倾入50cm高硅胶柱中，减压抽滤，以石油醚冲去低极性杂质，再以氯仿冲洗，收集滤液，旋干，得6-(5’-苯基-2’-噻吩基)-萘-2-醛4.2g。
在配有温度计、氮气保护装置、恒压滴液漏斗、磁力搅拌、冷凝回流装置的四口100ml烧瓶中，加入锌粉(3.9g，60mmol)，绝对无水四氢呋喃30ml，于恒压滴液漏斗中加入四氯化钛(6.6ml，30mmol)，待用。开动搅拌，冰水降温至-10℃。于30分钟内滴加四氯化钛，加毕，升温至回流，保持回流2小时。将6-(5’-苯基-2’-噻吩基)-萘-2-醛3.14g(10mmol)溶于绝对无水四氢呋喃中30ml，于10分钟内滴加到上述反应液中，加毕，回流过夜。冷到0℃，抽滤，滤饼用5ml四氢呋喃淋洗，得黄绿色固体间杂有颗粒状金属钛。用水分离除去钛粒后，真空干燥得2.8g化合物1。
产物MS(m/e)：596；元素分析(C48H28S2)：理论值C：84.53％，H：4.73％，S：10.75；实测值C：84.51％，H：4.78％，S：10.71％。
实施例二  化合物12：
反应式：
Figure A20081000662400261
过程：
在氮气保护下，在250ml烧杯中加入2-吲哚7.0g 35.7mmol，Cu(OAc)20.8g 4.8mmol，2，4-二甲基吡啶2mL，十四酸1.104g4.8mmol，苯硼酸5.8g 48mmol甲苯100mL暴露在空气中搅拌24小时，过短柱，滤去黑色的粘稠物，石油醚重结晶，得到白色晶体5.8g。
以下步骤同实施例一，得到黄色固体2.4g，收率15.4％。
产物MS(m/e)：662.3；元素分析(C50H34N2)：理论值C：90.59％，H：5.13％，N：4.22％；实测值C：90.60％，H：5.17％，N：4.23％。
实施例三  化合物18
Figure A20081000662400271
在250mL三口瓶内加入5-溴-1，5，5-三甲氧基-1-乙烯基-3乙炔15g，硫酸镁30g，甲醇10mL，甲苯50mL，加分水器回流10小时，加入100mL盐酸搅拌2小时，分液，旋干有机层，得粘稠固体6.2g。
在氮气保护下，在250mL三口瓶中，6mL四氯化钛，8g锌粉回流2小时，100mL二氯甲烷，加入30g6-溴2-萘甲醛，回流4小时，过滤得到白色蜡状固体17g，将此固体加入100mL无水四氢呋喃中，冷却至-78℃，滴加丁基锂，搅拌1小时，加入20mL硼酸三甲酯，盐酸调节pH值至8，过滤，得到黄褐色固体。
在氮气保护下，在250mL三口瓶中加入上述粘稠固体和黄褐色固体，0.5g氯化钯，0.8g三苯基磷，回流10小时，柱色谱分离，乙酸乙酯与石油醚体积比为1∶1混合溶剂作为展开剂。
产物MS(m/e)：564.16；元素分析(C38H20N4O2)：理论值C：80.82％，H：3.54％，N：9.93％，O：5.67％；实测值C：80.84％，H：3.57％，N：9.92％O：5.67％。
实施例四  化合物19：
Figure A20081000662400281
在配有磁力搅拌器，分水器、冷凝回流装置及氮气保护装置的500ml三口烧瓶中，加入2-溴-5-碘噻吩28.9克(100mmol)，N-苯基萘胺24.1克(110mmol)，碘化铜1.9g(10mmol)、无水磷酸钾53g(200mmol)，加入邻二甲苯250ml。加热回流，反应24小时。停止加热，冷却到室温。产物以干柱分离，石油醚洗脱。收集滤液，旋去溶剂，得到N-苯基-N-萘基-5-溴-2-噻吩胺19.6g。
在配有磁力搅拌器及氮气保护装置的250ml三口烧瓶中，加入N-苯基-N-萘基-5-溴-2-噻吩胺19.0g(50mmol)，再加入100ml无水四氢呋喃，搅拌，降温至-78℃。向反应器中滴入0.06mol丁基锂，反应2小时，再滴入8.5ml硼酸三甲酯。反应搅拌过夜。加入10ml3M盐酸水解，分液，取有机相。浓缩产物，加入石油醚重结晶。得到N-苯基-N-萘基-5-胺基噻吩-2-硼酸7.1g。
在配有磁力搅拌器，冷凝回流装置及氮气保护装置的100ml三口烧瓶中，加入N-苯基-N-萘基-5-胺基噻吩-2-硼酸5.2克(15mmol)，6-溴-2-萘醛2.35克(10mmol)，醋酸钯0.022克(0.1mmol)，三苯基膦0.53克(0.2mmol)，碳酸钾3.45克(25mmol)，甲苯50ml。加热回流反应24小时。停止加热，冷却到室温。
将反应液倾入50cm高干柱中，减压抽滤，以石油醚冲去低极性杂质，再以氯仿冲洗，收集滤液，旋干，得6-(N-苯基-N-萘基-5’-胺基噻吩-2-基)-萘-2-醛3.15g。
在配有温度计、氮气保护装置、恒压滴液漏斗、磁力搅拌、冷凝回流装置的四口100ml烧瓶中，加入锌粉(1.95g，30mmol)，绝对无水四氢呋喃30ml，于恒压滴液漏斗中加入四氯化钛(3.3ml，15mmol)，待用。开动搅拌，冰水降温至-10℃。于30分钟内滴加四氯化钛，加毕，升温至回流，保持回流2小时。将6-(N-苯基-N-萘基-5’-胺基噻吩-2-基)-萘-2-醛2.28g(5mmol)溶于绝对无水四氢呋喃中30ml，于10分钟内滴加到上述反应液中，加毕，回流过夜。冷到0℃，抽滤，滤饼用5ml四氢呋喃淋洗，得黄绿色固体间杂有颗粒状金属钛。用水分离除去钛粒后，真空干燥得1.2g。
产物MS(m/e)：879；元素分析(C62H42S2N2)：理论值C：84.70％，H：4.82％，S：7.29，N：3.19％；实测值C：84.71％，H：4.78％，S：7.31％，N：3.20％。
实施例五  化合物29
反应式：
Figure A20081000662400291
过程：
在氮气保护下，在500mL的三口瓶内加入22.3g对溴苯基噁二唑，20g二苯胺，0.5g醋酸钯，0.7g三苯基磷，50g碳酸钾，200mL甲苯，回流6小时，柱色谱分离，滤出黑色粘稠物质，旋干，乙酸乙酯重结晶得到灰白色固体25g.将上述固体溶于200mL无水四氢呋喃中，冷却至-78℃，慢慢滴加150mL丁基锂，搅拌1小时候递加200mL硼酸三甲酯，升至室温后调节PH＝10，析出浅黄色固体，过滤，烘干得到23g.将上诉固体加入250mL三口瓶内，加入6-溴-2萘缩醛14g，0.6g氯化钯，1g三苯基磷，50g碳酸钾，150mL体积比1∶1∶1的甲苯，乙醇，水的混合溶剂回流10小时。加入50mL10％的盐酸，搅拌4小时，分液，旋干得到黄色固体7.2g，将得到的固体溶于100mL无水四氢呋喃中，加入6g6-溴-2-萘磷酸二甲酯，加入3.6g氢化钠，回流4小时候加入冰水中析出黄色固体。过滤，氯仿重结晶得到黄色固体5.3g，将上述黄色固体加入50mL无水四氢呋喃，冷却至-78℃，慢慢滴加30mL丁基锂，搅拌1小时候，滴入10mL N，N-二甲基甲酰胺，搅拌下升至室温，加入10mL 10％的盐酸，乙酸乙酯萃取，旋干，乙醇煮，得到黄色固体3.2g将上述固体加入40mL无水四氢呋喃中，加入4g四氢铝锂，冰浴下搅拌4小时，滴加入10mL水，过滤，旋干得到浅黄色固体，并把所得固体分散在30mL二氯甲烷中，冷却至-30℃，滴加3mL三溴化磷，搅拌2小时候滴加20mL甲醇，析出黄色固体，过滤，干燥得到2.4g固体。将上述固体溶于15mL甲苯中，加入0.08g氯化钯和1.2g三苯基磷，5g碳酸钾，回流5小时，柱色谱分离，石油醚∶二氯甲烷体积比4∶1作为淋洗剂得到橙黄色固体2.2g，收率68.1％
产物MS(m/e)：848.15；元素分析(C61H44N4O)：理论值C：86.31％，H：5.19％，N：6.60％，O：1.89％；实测值C：86.29％，H：5.22％，N：6.60％O：1.88％。
实施例六  化合物32：
反应式
Figure A20081000662400311
氮气保护下，在加有磁力搅拌三口瓶中加入丙二酸二乙酯16g 100mmol，2-溴-甲酰溴20mL，氢化钠5g200mmol，95％乙醇200mL，加热回流4小时，加入50mL水，氯仿萃取得到旋干得到浅黄色液体11mL。
在氮气保护下，在加有磁力搅拌的三口瓶内加入4.8g 40mmol苯甲脒，5mL上步得到浅黄色液体，3.4g乙醇钠50mmol，100mL乙醇回流10小时，加入50mL水，二氯甲烷萃取，旋干得到白色固体8.5g。
将上述固体加入密封瓶内，加入100mL无水四氢呋喃，通入甲基胺气体，加压至2个大气压，反应2小时，减压候不处理直接用于下一步反应。
将上诉反应液加入三口瓶内，加入3.8g100mmol四氢铝锂，搅拌2小时，加入10mL水，过滤，旋干得到白色固体6.1g。
将上述白色固体加入三口瓶内，加入10mL丙酮，20mL，10％的盐酸水溶液，搅拌10小时过滤，烘干得到白色固体4.6g。
将上述白色固体加入三口瓶内，加入50mL无水四氢呋喃，丙酮浴，液氮冷却至-70℃，缓慢滴加10mL丁基锂，然后滴加20mL硼酸三甲酯，搅拌2小时，慢慢地入5mL水，调节pH至4，过滤，得到白色固体2.8g。
将上述白色固体加入50mL甲苯，加入3.0g，2-溴-6-萘缩醛2.5g，氯化钯0.05g，三苯基膦0.15g，碳酸钾4g，回流10小时，过短柱，二氯化碳淋洗，旋干，溶于10mL丙酮，加入10mL，10％盐酸水溶液，搅拌4小时，过滤得到黄色固体3.6g。
在氮气保护下，在50mL三口烧瓶内加入20mL无水四氢呋喃，1g锌粉，慢慢滴加2mL四氯化钛，在-30℃下滴加完毕后，升温至回流2小时，将3.6g上述醛溶于40mL无水四氢呋喃中回流4小时，冷却，过滤，用水分离除去钛粒后真空干燥，得到橙色固体1.8g
产物MS(m/e)：694.3；元素分析(C48H34N6)：理论值C：82.99％，H：4.90％，N：12.10％；实测值C：82.97％，H：4.93％，N：12.10％。
下面是本发明化合物的应用实施例：
制备器件的优选实施方式：
OLED器件的典型结构为：基片/阳极/空穴传输层(HTL)/有机发光层/电子传输层(ETL)/阴极。
基片为透明的，可以是玻璃或是柔性基片，柔性基片采用聚酯类、聚酰亚胺类化合物中的一种材料；阳极层可以采用无机材料或有机导电聚合物，无机材料一般为氧化铟锡(以下简称ITO)、氧化锌、氧化锡锌等金属氧化物或金、铜、银等功函数较高的金属，最优化的选择为ITO，有机导电聚合物优选为聚噻吩/聚乙烯基苯磺酸钠(以下简称PEDOT∶PSS)、聚苯胺(以下简称PANI)中的一种材料；阴极层一般采用锂、镁、钙、锶、铝、铟等功函数较低的金属或它们与铜、金、银的合金，或金属与金属氟化物交替形成的电极层，本发明优选为依次的Mg:Ag合金层、Ag层和依次的LiF层、Al层；空穴传输层一般采用三芳胺类材料，本发明优选为N，N’-二-(1-萘基)-N，N’-二苯基-1，1-联苯基-4，4-二胺(NPB)；或者本发明中的材料中的一种，电子传输层，一般为金属有机配合物，优选如三(8-羟基喹啉)铝、三(8-羟基喹啉)镓、(水杨醛缩邻胺苯酚)-(8-羟基喹啉)合镓(III)(以下分别简称Alq3、Gaq3、Ga(Saph-q))，也可为邻菲咯啉类，如4，7-二苯基-1，10-邻菲咯啉(以下简称Bphen)或本发明材料中的一种，本发明的有机发光层中包含了本发明提出的材料，其可以直接发光，也可以作为染料掺杂在相应的主体材料中发光，优选的主体材料为ADN、Alq3、Gaq3、Ga(Saph-q)，或本发明中的材料。
按照以下方法制备本发明的一系列有机电致发光器件：
(1)使用清洗剂、去离子水和有机溶液分几步清洗带有阳极的玻璃基片；
(2)通过真空蒸发的方法蒸镀器件的空穴传输层；
(3)再继续蒸镀包含本发明的红光材料的发光层；
(4)继续蒸镀器件的电子传输层；
(5)再通过蒸镀或溅射的方法制备金属阴极。
实施例一  制备器件OLED-1～OLED-3
制备OLED-1：将涂布了ITO透明导电层的玻璃板在商用清洗剂中超声处理，在去离子水中冲洗，在丙酮∶乙醇混合溶剂中超声除油，在洁净环境下烘烤至完全除去水份，用紫外光清洗机照射10分钟，并用低能阳离子束轰击表面。
把上述带有阳极的玻璃基片置于真空腔内，抽真空至1×10-5～9×10-3Pa，在上述阳极层膜上继续蒸镀NPB作为空穴传输层，蒸镀速率为0.1nm/s，蒸镀膜厚为50nm；
在空穴传输层之上，继续蒸镀一层掺杂有化合物1的Alq3作为器件的发光层，化合物2与Alq3的蒸镀速率比为1∶100，化合物1在Alq3中的掺杂浓度为3wt％，其蒸镀总速率为0.1nm/s，蒸镀总膜厚为30nm；
再继续蒸镀一层Alq3材料作为器件的电子传输层，其蒸镀速率为0.1nm/s，蒸镀总膜厚为20nm；最后，在上述电子传输层之上依次蒸镀Mg:Ag合金层和Ag层作为器件的阴极层，其中Mg:Ag合金层的蒸镀速率为2.0-3.0nm/s，厚度为100nm，Ag层的蒸镀速率为0.3nm/s，厚度为100nm。
按照上述方法制备OLED-2和OLED-3，仅是改变了化合物1在Alq3中的掺杂浓度，器件的性能详见表1：
器件编号 器件结构组成   发光波长nm   电流密度A/m2   CIE(X，Y)   效率cd/A
  OLED1   NPB/Alq:3％化合物1/Alq/Mg:Ag/Ag   518   4293.02   0.23，0.09   5.2
  OLED2   NPB/Alq:7％化合物1/Alq/Mg:Ag/Ag   520   4591.43   0.22，0.07   4.2
  OLED3   NPB/Alq:15％化合物1/Alq/Mg:Ag/Ag   518   4439.63   0.24，0.12   2.9
实施例二  制备器件OLED-4～OLED-7
制备OLED-4：将涂布了ITO透明导电层的玻璃板在商用清洗剂中超声处理，在去离子水中冲洗，在丙酮∶乙醇混合溶剂中超声除油，在洁净环境下烘烤至完全除去水份，用紫外光清洗机照射10分钟，并用低能阳离子束轰击表面。
把上述带有阳极的玻璃基片置于真空腔内，抽真空至1×10-5～9×10-3Pa，在上述阳极层膜上继续蒸镀NPB作为空穴传输层，蒸镀速率为0.1nm/s，蒸镀膜厚为50nm；
在空穴传输层之上，继续蒸镀一层掺杂有C545T的化合物12(化合物12作为主体染料)作为器件的发光层，C545T与化合物12的蒸镀速率比为1∶100，C545T在化合物12中的掺杂浓度为3wt％，其蒸镀总速率为0.1nm/s，蒸镀总膜厚为30nm；
再继续蒸镀一层Alq3材料作为器件的电子传输层，其蒸镀速率为0.1nm/s，蒸镀总膜厚为20nm；
最后，在上述电子传输层之上依次蒸镀Mg:Ag合金层和Ag层作为器件的阴极层，其中Mg:Ag合金层的蒸镀速率为2.0-3.0nm/s，厚度为100nm，Ag层的蒸镀速率为0.3nm/s，厚度为100nm。
按照实施例的方法制备器件OLED-4～OLED-6，仅是改变了C545T在化合物12中的掺杂浓度，器件的性能详见表2：
器件编号 器件结构组成   发光波长nm 电流密度A/m2 CIE(X，Y) 效率cd/A
  OLED4   NPB/化合物12:3％C545T/Alq/Mg:Ag/Ag   514   2399.64   0.31，0.66   10.2
  OLED5   NPB/化合物12:7％C545T/Alq/Mg:Ag/Ag   522   2408.35   0.31，0.64   8.6
  OLED6   NPB/化合物12:10％C545T/Alq/Mg:Ag/Ag   520   2977.16   0.29，0.70   4.9
实施例三  化合物32空穴迁移率的测定
将涂布了ITO透明导电层的玻璃板在商用清洗剂中超声处理，在去离子水中冲洗，在丙酮∶乙醇混合溶剂中超声除油，在洁净环境下烘烤至完全除去水份，用紫外光清洗机照射10分钟，并用低能阳离子束轰击表面。
把上述带有阳极的玻璃基片置于真空腔内，抽真空至1×10-5～9×10-3Pa，在上述阳极层膜上继续蒸镀化合物32作为空穴传输层，蒸镀速率为0.1nm/s，蒸镀膜厚为200nm；
最后，在上述电子传输层之上依次蒸镀Mg:Ag合金层和Ag层作为器件的阴极层，其中Mg:Ag合金层的蒸镀速率为2.0-3.0nm/s，厚度为100nm，Ag层的蒸镀速率为0.3nm/s，厚度为100nm。
载流子迁移率由实验室搭建的渡越时间测量法测量结果为10-4m2/sV。

Claims (6)

1、一种化合物，结构通式如下所示：
Figure A20081000662400021
X，Y分别独立选自含一至三个杂原子的C4-20的五元或六元的芳香环，或选自含有一至三个杂原子的C6-20 的芳香稠环，或选自亚甲基，且X，Y不同时为亚甲基；
Ar1，Ar2分别独立选自氢原子、氟原子、羰基、腈基、酰氧基、亚乙烯基、C1-30的烷基或取代烷基、C1-30的烷氧基或取代的烷氧基、C2-30的烷基氨基或取代的烷基氨基、C1-30的烷硫基或取代烷硫基、C6-20的芳基或取代芳基、C6-20的稠环芳基或C6-30的芳胺基团。
2、根据权利要求1的化合物，其特征在于，X，Y分别独立选自吡咯基、噻吩基、呋喃基、吡啶基、喹啉基、异喹啉基、咔唑基、菲啶基、苯并噻吩基、苯并呋喃、吡唑基、咪唑基、呋咱基、硫杂吡咯基、氮杂呋喃基、氮杂噻吩基、硫杂嘧啶基、硫杂吡啶基、硫杂喹啉基、硫杂异喹啉基、硫杂哒嗪基、硫杂嘧啶基、硫杂吡嗪基、硫杂哒嗪基、噁二唑、嘧啶基、吡嗪基、氮杂苯并噻吩基、硫杂吲哚、硫杂异吲哚、硫杂吲唑、吡唑并喹啉、亚甲基X，Y相等或不等，X，Y不同时为亚甲基；
Ar1，Ar2分别独立选自氢原子、甲基、乙基、异丙基、叔丁基、羰基、腈基、酰氧基、亚乙烯基、甲氧基、乙氧基、异丙氧基、叔丁基氧基、N，N-二甲基胺基、N，N-二乙基胺基、甲硫基、乙硫基、异丙基硫基、叔丁基硫基、氟原子、苯基、联苯基、萘基、蒽基、芘基、芴基、并四苯基、N，N-二苯基胺基、N，N-二(α-萘基)胺基、N，N-二(β-萘基)胺基、N-苯基-N-(α-萘基)胺基、N-苯基-N-(β-萘基)胺基、N-甲基-N-苯基胺基、咔唑基、对咔唑基苯基、对N’N-二苯基氨基苯基。
3、根据权利要求1的化合物，其中优选的X、Y、Ar1、Ar2的分子结构式如下：
Figure A20081000662400022
Figure A20081000662400031
Figure A20081000662400041
4、根据权利要求1的化合物，其中优选化合物的分子结构式如下：
Figure A20081000662400042
Figure A20081000662400061
Figure A20081000662400071
Figure A20081000662400081
Figure A20081000662400091
Figure A20081000662400101
5、权利要求1所述的化合物在有机电致发光器件中的应用，可用作发光材料或电子传输和空穴阻挡材料。
6、一种有机电致发光器件，包括第一电极和第二电极，以及位于两电极之间的有机功能层，其特征在于，有机功能层中的至少一层包含具有下列结构式的化合物：
Figure A20081000662400121
X，Y分别独立选自含一至三个杂原子的C4-20的五元或六元的芳香环，或选自含有一至三个杂原子的C6-20 的芳香稠环，或选自亚甲基，且X，Y不同时为亚甲基；
Ar1，Ar2分别独立选自氢原子、氟原子、羰基、腈基、酰氧基、亚乙烯基、C1-30的烷基或取代烷基、C1-30的烷氧基或取代的烷氧基、C2-30的烷基氨基或取代的烷基氨基、C1-30的烷硫基或取代烷硫基、C6-20的芳基或取代芳基、C6-20的稠环芳基或C6-30的芳胺基团。
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