CN1674747A - 有机电致发光器件 - Google Patents

有机电致发光器件 Download PDF

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CN1674747A
CN1674747A CNA2005100564575A CN200510056457A CN1674747A CN 1674747 A CN1674747 A CN 1674747A CN A2005100564575 A CNA2005100564575 A CN A2005100564575A CN 200510056457 A CN200510056457 A CN 200510056457A CN 1674747 A CN1674747 A CN 1674747A
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李敬勋
徐正大
郑贤哲
朴春键
金重根
金成甲
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LG Display Co Ltd
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Abstract

本发明公开一种有机电致发光器件，以实现改进亮度和降低驱动电压，该有机电致发光器件包括：阳极、空穴注入层、空穴传输层、发射层和阴极，其中，空穴注入层和空穴传输层由下面化学式1所表示的材料形成。

Description

有机电致发光器件
本申请要求于2004年3月22日提交的韩国申请No.10-2004-0019356为优先权，在此将其引入作为参考，视为在本文中被完全提出。
技术领域
本发明涉及一种有机电致发光器件。
背景技术
一般地，有机电致发光器件包括在电子注入电极(阴极)和空穴注入电极(阳极)之间形成的有机层。在这种状态下，根据电荷被注入到有机层，使电子和空穴成为一对，然后湮灭，因而产生光。
有机电致发光器件可形成在如塑料的透明材料的柔性衬底上。另外，与等离子显示器或无机电激发光EL显示器相比，有机电致发光器件可在低于10V的更低电压下操作。并且，有机电致发光器件实现了低功率消耗和高彩色品质。此外，有机电致发光器件可显示红色、绿色和蓝色三种颜色，因而有机电致发光器件作为下一代显示器件已引起很大的关注。
制造有机电致发光器件的方法描述如下：
(1)首先，阳极材料涂覆在透明衬底上。例如，如ITO(铟锡氧化物)的阳极材料被广泛使用。
(2)然后，空穴注入层HIL形成在阳极材料上。此时，空穴注入层HIL通常以涂覆10nm～30nm厚度的铜酞菁(CuPC)的方法而形成。
(3)之后，空穴传输层HTL被涂覆在空穴注入层HIL上。此时，空穴传输层HTL以沉积30nm～60nm厚度的4，4’-二[N-(1-萘基)-N-苯氨基]-联苯(4，4’-bis[N-(1-naphyhyl)-N-phentylamino]-biphenyl)(NPB)的方法而形成。
(4)有机发射层形成在空穴传输层上。在这种情况下，根据所需，掺杂剂可被加入到有机发射层。在发绿光的情况下，三(8-羟基-喹啉酸铝)(tris(8-hydroxy-quinolate)aluminum)(Alq3)作为有机发射层被沉积30nm～60nm的厚度，及MQD(N-甲基喹吖啶酮)被通常用作掺杂剂。
(5)然后，电子注入/传输层EITL可在有机发射层上形成，或者电子传输层ETL和电子注入层EIL可顺序地形成在有机发射层上。在发绿光的情况下，Alq3具有较大的电子传输能力，从而无需形成电子注入/传输层。
(6)接下来，阴极形成在电子传输层(或电子注入/传输层)上，并且然后根据所需，涂覆保护层，从而完成有机电致发光器件。
在有机电致发光器件的上述结构中，空穴注入和传输层会影响器件的亮度和驱动电压。即，空穴注入和传输层对器件的寿命长短起重要作用。因此，有必要研究和开发用于空穴注入和传输层的材料，以实现改进亮度和降低驱动电压。
发明内容
因此，本发明涉及一种有机电致发光器件，该有机电致发光器件实质上避免了由于现有技术的限制和缺点而引起的一种或多种问题。
本发明的目的是提供一种有机电致发光器件以实现改进亮度和降低驱动电压。
本发明的其它的优点、目的和特性在下面的说明中被部分地阐明，并且通过本领域普通技术人员对下面的说明的考查部分地将变得清楚或者可以从本发明的实施中理解。本发明的目的和其它优点可通过所撰写的说明书和权利要求书以及附图中特别指出的结构而实现和达到。
根据本发明的目的，为了实现这些目的和其它优点，正如在本文中具体地和广泛地描述，有机电致发光器件包括阳极、空穴注入层、空穴传输层、发射层和阴极，其中，空穴注入层和传输层由下面化学式1所表示的材料形成，
化学式1
应当理解，本发明前面一般性描述和下面详细描述均是范例性和解释性的并对所要求保护的发明提供更进一步的说明。
具体实施方式
现对本发明的优选实施方式进行详细描述，本发明的实施例通过附图来说明。在全部附图中任何地方所使用的相同参考数字表示相同或相似的部分。
在下文中，将对根据本发明优选实施例的有机电致发光器件描述如下。
根据本发明选实施例的有机电致发光器件由阳极、空穴注入层、空穴传输层、发射层和阴极形成。其中，空穴注入层和/或传输层由下面化学式1所表示的材料形成，
化学式1
Figure A20051005645700261
其中，‘n’为1～4的正数，‘R1’或‘R2’选自取代或未取代的芳基、杂环基、脂族基或氢组成的组。
此外，‘R1’和‘R2’中至少一个可选自取代或未取代的苯基、联苯基、吡啶基、萘基、喹啉基、异喹啉基、芴基、三联苯基、蒽基、菲基、甲基、乙基、丙基、异丙基等。
每个取代的‘R1’和‘R2’中的各取代基可选自包含烷基、芳基、烷氧基、卤素、氰基、烷基芳基、乙烯芳基等的组。
此外，取代基可选自包含甲基、乙基、丙基、异丙基、t-丁基、环己基、甲氧基、乙氧基、丙氧基、丁氧基、氟、氯、苯氧基、甲苯氧基等的组。
因此，用于空穴注入层和空穴传输层的材料可选自下面化学式2中的任一材料，‘R1’和‘R2’被使用于其中：
Figure A20051005645700281
Figure A20051005645700291
Figure A20051005645700311
Figure A20051005645700321
Figure A20051005645700341
Figure A20051005645700371
Figure A20051005645700391
Figure A20051005645700401
Figure A20051005645700411
Figure A20051005645700421
此时，用于空穴注入层和/或空穴传输层的材料之一的HM-32将被合成如下。
1、[(4-溴-苯基)-二苯基胺]的合成
Figure A20051005645700481
在两颈圆底烧瓶中，50g 0.30mol的二苯胺、104g 0.44mol的二溴苯、7.4g 4％mol的BINAP(2，2’-二(联苯基膦基)-1，1’-联萘)、2.0g 3％mol的Pd(OAc)2(醋酸钯(II))和42.6g 0.44mol的NaOtBu(叔丁醇钠)溶解在400ml甲苯中，然后通过回流维持24小时。反应完成后，冷却装有产物溶液的烧瓶，然后，反应溶剂甲苯从产物溶液中除去。之后，不含甲苯的产物溶液与二氯甲烷和水反应，然后从中除去二氯甲烷，用比例为3∶1的二氯甲烷和己烷的溶剂进行硅胶柱色谱法。之后，溶剂从完成硅胶柱色谱法的产物溶液中除去，然后用二氯甲烷和石油醚过滤和重结晶，因而得到36.5g 40％的白色固体(4-溴-苯基)-二苯胺。
2、(N，N，N’-三苯基-苯-1，4-二胺)的合成
在两颈圆底烧瓶中，12g，0.037mol的(4-溴-苯基)-二苯胺、16.26ml，0.178mol的苯胺、0.4g，3％mol的BINAP、7.4g，4％mol的Pd(OAc)2和17.2g，0.178mol的NaOtBu溶解在300mL甲苯中，然后通过回流维持18小时。反应完成后，冷却装有产物溶液的烧瓶，然后，反应溶剂甲苯从产物溶液中除去。之后，不含甲苯的产物溶液与二氯甲烷和水反应，然后从中除去二氯甲烷，用比例为2∶1的二氯甲烷和己烷的溶剂进行硅胶柱色谱法。之后，溶剂从完成硅胶柱色谱法的产物溶液中除去，然后用二氯甲烷和石油醚过滤和重结晶，因而得到11.0g 88％的白色固体N，N，N’-三苯基-苯-1，4-二胺。
3、N，N’-二(3-溴苯基)-N，N’-联苯基-1，4-苯二胺的合成
Figure A20051005645700491
在两颈圆底烧瓶中，5g 0.019mol的N，N’-联苯基-1，4-苯二胺、45g0.19mol的二溴苯、0.71g 6％mol DPPf[1，1’-二(联苯基膦基)二茂铁]、2.0g4％mol的Pd(OAc)2和7.0g 0.07mol的NaOtBu溶解在150ml甲苯中，然后在110℃下加热50小时。反应完成后，冷却装有产物溶液的烧瓶，然后，反应溶剂甲苯从产物溶液中除去。之后，不含甲苯的产物溶液溶解在二氯甲烷中，然后进行硅胶柱色谱法(二氯甲烷)。然后，溶剂从进行了硅胶柱色谱法的产物溶液中除去，然后用二氯甲烷和甲醇过滤和重结晶，从而得到6.5g 60％的灰色固体N，N’-二(3-溴苯基)-N，N’-联苯基-1，4-苯二胺。
4、HM-32的合成
在两颈圆底烧瓶中，2.54g 0.0066mol的N，N，N’-三苯基-苯-1，4-二胺、1.5g 0.0026mol N，N’-二(3-溴苯基)-N，N’-联苯基-1，4-苯二胺、0.7g4％mol的BINAP、0.02g 3％mol的Pd(OAc)2和17.2g 0.0092mol的NaOtBu溶解在100ml甲苯中，然后通过回流维持40小时。反应完成后，冷却装有产物溶液的烧瓶，然后，反应溶剂甲苯从产物溶液中除去。之后，不含甲苯的产物溶液被甲醇过滤，然后溶解在氯苯中。然后，溶解在氯苯中的溶液进行硅胶柱色谱法，从而从溶液中除去杂质和溶剂。接着，不含杂质和溶剂的溶液使用氯苯和己烷过滤和重结晶，从而得到1.8g 64％的白色固体HM-32。
在下文中，根据本发明使用空穴注入层或空穴传输层材料的有机电致发光器件的优选实施例将说明如下。
实施例1(HM-32用于空穴注入层的材料)
首先，ITO玻璃衬底形成图案3mm×3mm的电致发光面积，清洁ITO玻璃衬底。然后，ITO玻璃衬底装载在真空室内，基本压力设定为1×10-6torr。有机材料按照HM-32(600)/NPB(400)/Alq3(C6)(200，3％)/Alq3(400)/LiF(5)/Al(1000)的顺序在ITO玻璃衬底上形成。如果空穴注入层由HM-32形成，在1mA的电流下，显示亮度为1720cd/m2，驱动电压为9.19V，其中CIE x＝0.335和y＝0.621。
实施例2(HM-02用于空穴传输层的材料)
首先，ITO玻璃衬底形成图案3mm×3mm的电致发光面积，清洁ITO玻璃衬底。然后，ITO玻璃衬底装载在真空室内，基本压力设定为1×10-6torr。有机材料按照CuPC(200)/HM-02(400)/Alq3(C6)(200，3％)/Alq3(400)/LiF(5)/Al(1000)的顺序在ITO玻璃衬底上形成。如果空穴传输层由HM-02形成，其在1mA时，显示亮度为1720cd/m2，驱动电压为9.05V，其中CIE x＝0.335和y＝0.621。
对比本发明，现有技术由CuPC形成空穴注入层的有机电致发光器件将被描述如下。
将ITO玻璃衬底形成图案3mm×3mm的电致发光面积之后，清洁ITO玻璃衬底。然后，ITO玻璃衬底装载在真空室内，基本压力设定为1×10-6torr。有机材料按照CuPC(200)/NPB(400)/Alq3(C6)(300，3％)/Alq3(400)/LiF(5)/Al(1000)的顺序在ITO玻璃衬底上形成。如果空穴注入层由CuPC形成，其在1mA时，显示亮度为1680cd/m2，驱动电压为9.20V，其中CIE x＝0.339和y＝0.619。此时，CuPC、NPB、Alq3和C6可由下面的化学式3表示：
如上所述，在现有技术中，显示亮度为1680cd/m2，驱动电压为9.20V。然而，根据本发明以HM-32形成空穴注入层的情况下，亮度/驱动电压显示为1720cd/m2(9.19V)。如果空穴传输层由HM-02形成，显示亮度为1720cd/m2，驱动电压为9.05V。即，根据本发明的有机电致发光器件实现了亮度的改进和驱动电压的降低。
在本发明的优选实施例中，空穴注入层或空穴传输层由具有化学式1结构的材料形成。但是，即使空穴注入层或空穴传输层由具有化学式3的材料形成，也可能改进亮度和降低驱动电压。此外，空穴注入层和空穴传输层都可由具有化学式1的材料形成，以改进亮度和降低驱动电压。
如上所述，根据本发明的有机电致发光器件具有如下优点。
在根据本发明的有机电致发光器件中，空穴注入层和空穴传输层由具有上述化学式1的材料形成，从而可能改进亮度和降低驱动电压，因而通过改进操作特性来增加该器件的寿命长短。
可对本发明作出各种修改和变化，这对本领域技术人员是显而易见的。因此，本发明包括了落在附属权利要求和其等效范围内的本发明的修改和变化。

Claims (5)

1、一种有机电致发光器件，包括：
阳极、空穴注入层、空穴传输层、发射层和阴极，其中，空穴注入层和空穴传输层由下面化学式1所表示的材料形成：
其中，‘n’为1～4的正数，且‘R1’或‘R2’选自包含取代或未取代的芳基、杂环基、脂族基或氢的组。
2、根据权利要求1所述的有机电致发光器件，其特征在于，‘R1’和‘R2’中至少一个选自取代或未取代的苯基、联苯基、吡啶基、萘基、喹啉基、异喹啉基、芴基、三联苯基、蒽基、菲基、甲基、乙基、丙基、异丙基等。
3、根据权利要求1所述的有机电致发光器件，其特征在于，各个取代的‘R1’和‘R2’中的取代基可选自包含烷基、芳基、烷氧基、卤素、氰基、烷基芳基、乙烯芳基等的组。
4、根据权利要求3所述的有机电致发光器件，其特征在于，取代基可选自包含甲基、乙基、丙基、异丙基、t-丁基、环己基、甲氧基、乙氧基、丙氧基、丁氧基、氟、氯、苯氧基、甲苯氧基等的组。
5、根据权利要求1所述的有机电致发光器件，其特征在于，空穴注入层和空穴传输层由具有下面化学式2的任一种材料形成：
Figure A2005100564570003C1
Figure A2005100564570004C1
Figure A2005100564570009C1
Figure A2005100564570011C1
Figure A2005100564570012C1
Figure A2005100564570016C1
Figure A2005100564570018C1
Figure A2005100564570020C1
Figure A2005100564570021C1
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