CN106432107A - 化合物及使用其制成的电子组件 - Google Patents

化合物及使用其制成的电子组件 Download PDF

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CN106432107A
CN106432107A CN201610633265.4A CN201610633265A CN106432107A CN 106432107 A CN106432107 A CN 106432107A CN 201610633265 A CN201610633265 A CN 201610633265A CN 106432107 A CN106432107 A CN 106432107A
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陈建添
陈济中
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Nichem Fine Technology Co Ltd
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Abstract

本案系提供一种化合物。所述化合物包括：顺式二苯乙烯段；具有四键原子的桥接原子段，以所述四键原子的两个键连接于所述顺式二苯乙烯段，形成七员环结构段；以及喹啉段，连接于所述顺式二苯乙烯段。

Description

化合物及使用其制成的电子组件
技术领域
本发明提出一种化合物及电子组件，特别是一种用于电子组件中发光材料或有机材料的化合物。
背景技术
最早的有机发光二极管(OLED)是由伊斯特曼柯达(Eastman Kodak)公司经由真空蒸镀程序制作，柯达公司的唐(Tang)和凡斯赖克(VanSlyke)于带有芳二胺基的有机层之透明铟锡氧化物(ITO)玻璃上沉积电子传输材料，例如Alq3，随后将金属电极以蒸镀方式沉积于所述Alq3层上，制造成有机电激发光(EL)组件。所述有机EL组件由于具有高亮度、快反应速度、轻量、紧密度、全彩色、无视角差异、无需使用液晶显示器(LCD)背光板以及低能耗，目前已成为新一代的发光组件或显示器。
近年来、一些像是电子传输层及电洞传输层等中间层被设置于阴极及阳极之间，以提高OLED的电流效率及功率效率。例如，如图1中所例示的OLED 100被设计成由阴极11、电子注入层12、发光层15、电洞传输层17及阳极18所构成。
从组件功能概念来看，从OLED 100发出的光线起因于所述发光层15中的电子及电洞重组所产生的激子。然而，根据理论推测，单重态的激子与三重态的激子之比例为3∶1，因此，当小分子荧光材料用于所述OLED 1’的所述发光层时，约有25％激子被用于发光，以及其余75％三重态激子经由非发光机制而损失。所以，一般的荧光材料可已达成的量子效率，相对于原件中外部量子效率5％之量，上限为25％。
再者，研究人员还发现特定的电洞传输式材料可以同时达成电子限制能力，像是由以下化学式1’及2’所表示的材料。所述化学式1’表示了被缩写称为TCTA的三(4-肼甲酰基-9-基-苯基)胺。所述化学式2’表示了被缩写称为NPB的N，N’-二(1-萘基)-N，N’-二苯基-(1，1’-联苯基)-4，4’-二胺。
此外，在OLED应用中为了有效的蓝色发光效能，研究人员开发出基于三芳基胺基二聚物形态的电洞传输式蓝色发光体，像是发明人于实验室中开发得到由以下化学式3’、4’及5’所代表的IDE-102、N-STIF-N，以及螺二芴为基底的系统。
目前，为了有效提升OLED的发旋光性能，OLED制造商及研究人员已付出很多努力而开发得到具有电洞阻挡功能的电子传输材料，像是由以下化学式6’到10’所分别代表的TmPyPb、TPBi、3TPYMB、BmPyPb以及DPyPA。TmPyPb是3，3′-[5′-[3-(3-吡啶基)苯基][1，1′：3′，1″-三苯]-3，3″-二基]双吡啶的缩写，TPBi是1，3，5-Tris(1-苯基-1H-苯并咪唑-2-基)苯的缩写，3TPYMB是参(2，4，6-三甲基-3-(吡啶-3-基1)苯基)硼烷的缩写，BmPyPb是1，3-双(3，5-双吡啶-3-基-苯基)苯的缩写，以及DPyPA是9，10-双(3-(吡啶-3-基)苯基)蒽的缩写。
尽管各种具有电洞阻挡功能的电子传输材料已开发，使用这些电子传输材料的磷光OLED还无法完成同时具有长时间生命期的装置以及优良的发光效率。因此，由于习知或商业上具有电洞阻挡功能的电子传输材料仍有缺陷，本案发明人已尽最大努力进行发明性研究，且终于提供一系列的具有氰基芳香基及/或氰基杂芳香基的喹啉融合螺顺式二苯乙烯/芴化合物，作为用于OLED的电洞阻挡型的电子传输体以及发光体。
发明内容
本发明之一面向系提供一种化合物，所述化合物包括：顺式二苯乙烯段；具有四键原子的桥接原子段，以所述四键原子的两个键连接于所述顺式二苯乙烯段，形成七员环结构段；以及喹啉段，连接于所述顺式二苯乙烯段。
本发明之另一面向系提供一种电子组件，所述电子组件由化合物制成，其中所述化合物包括：顺式二苯乙烯段；具有四键原子的桥接原子段，以所述四键原子的两个键连接于所述顺式二苯乙烯段，形成七员环结构段；以及喹啉段，连接于所述顺式二苯乙烯段。
本发明之又一面向系提供一种制造由化学式4来表示的化合物的方法，
所述方法包括：将由化学式11来表示的化合物与酸反应。形成由化学式12来表示的化合物：
将由化学式12来表示的化合物与无水酸反应。形成由化学式13来表示的化合物：
以及将由化学式13来表示的化合物与无水物反应。形成由化学式14来表示的化合物：
其中R为H、卤素、-Ar、-CN、-CF3、-Ar-F、芳香胺基、或由化学式3a、3b、3c、3d、3e、3f、3g、3h、3j、3k、3j、3m或3n来表示：
其中卤素为F、Cl、Br或I，Ar及G为苯基，以及所述芳香胺基为-NR4R5，R4或R5为H、苯基或萘基，n＝1或2，以及m＝1、2或3。
本领域技术人员在阅读以下详细实施方式的叙述及所附的图式之后，将对本发明的目的及优点有更清楚明白的了解。
附图说明
图1显示现有的OLED的结构。
图2显示本发明制成OLED的一实施例的结构。
图3显示本发明制成OLED的另一实施例的结构。
主要组件符号说明
11、21：阴极
12、22：电子注入层
15、25：发光层
17、27：电洞传输层
19、29：阳极
23：电子传输层
24：电洞阻挡层
26：电子阻挡层
27：电洞传输层
28：电洞注入层
30：基板
33：电洞阻挡型电子传输层
100、200、300：有机发光二极管
具体实施方式
本发明将藉由下述实施例并配合图示，作进一步的详细说明。值得一提的是，本发明下列实施例的叙述仅用于说明和描述，并非用来限制本发明至任何所揭露的精确形式或数据。
本发明提供一系列的喹啉融合螺顺式二苯乙烯/芴化合物及其衍生物，所述化合物包括顺式二苯乙烯段；具有四键原子的桥接原子段，以所述具有四键原子的两个键连接于所述顺式二苯乙烯段，形成七员环结构段；以及喹啉段，连接于所述顺式二苯乙烯段。所述化合物或其衍生物主要应用于OLED作为电子传输层、电洞阻挡层、电洞阻挡型的电子传输层、或发光层。依据本发明一种实施例的OLED 200如图2所示，OLED 200依序包括阴极21、电子注入层22、电子传输层23、电洞阻挡层24、发光层25、电子阻挡层26、电洞传输层27、电洞注入层28、阳极29以及基板30。当所述电子传输层23及所述电洞阻挡层24以单层形成，所述单层为由所述化合物或其衍生物所制成的电洞阻挡型的电子传输层33，如图3的OLED 300中所示。
前述之各种电子组件可应用于各种具有显示器的组件或装置，例如有机发光装置、太阳能电池装置、有机晶体管、侦测装置、平面显示器、计算机显示屏幕、电视、告示牌、室内或室外照明、室内或室外讯号灯、可挠式显示器、激光打印机、桌上型电话、可携式电话、遥控装置、平板计算机、笔记本电脑、数字相机、摄录像机、探视器、微型显示设备、车用装置、外墙显示设备、视听屏幕、或讯号装置。
本发明提供一系列的喹啉融合螺顺式二苯乙烯/芴化合物及其衍生物，其中所述喹啉段由化学式1来表示：
本发明提供一系列的喹啉融合螺顺式二苯乙烯/芴化合物及其衍生物，其中所述顺式二苯乙烯段由化学式2来表示：
其中R1或R11为H、卤素、-Ar、-CN、-CF3、-Ar-F、芳胺基、或由化学式3a、3b、3c、3d、3e、3f、3g、3h、3j、3k、31、3m或3n来表示：
其中卤素为F、Cl、Br或I，Ar及G为苯基，n＝1或2，m＝1、2或3，以及所述芳胺基为-NR4R5，其中R4或R5为H、苯基或萘基。更特定地，所述-NR4R5由化学式3p、3q或34来表示：
其中X为H或未取代或被取代的具有1-20个碳原子的烷基。
本发明提供一系列的喹啉螺顺式二苯乙烯/芴化合物及其衍生物，其中所述具有四键的原子为碳或硅，所述的桥接原子段以所述具有四键原子的另两个键至少其中之一与甲基或苯基连接；更特定地，所述由四键原子构成的桥接原子段为由化学式A1、A2、A3或A4所表示：
其中R3为H、叔丁基或萘基。
第一实施例
根据本发明第一实施例的有机化合物，为所述喹啉融合螺顺式二苯乙烯/芴化合物及其衍生物的其中之一，且为由化学式4A来表示：
其中R同前述之R1及R11。
第二实施例
根据本发明第二实施例的有机化合物，为喹啉融合螺顺式二苯乙烯/芴化合物及其衍生物的其中之一，且为由化学式4B来表示：
其中R1及R11同前述，R3为H、叔丁基或萘基。
第三实施例
根据本发明第三实施例的有机化合物，为喹啉融合螺顺式二苯乙烯/芴化合物及其衍生物的其中之一，且为由化学式4C来表示：
由化学式14表示的所述喹啉融合螺顺式二苯乙烯/芴化合物，其合成方法包括以下步骤。
步骤1
取5505.9毫克(10.7毫莫耳)由化学式11表示的化合物11放入反应瓶中，并加入15ml醋酸，再加入浓盐酸1.5rnL形成溶液，此时反应瓶内的溶液的颜色变为红色。在反应瓶上方安装回流装置，将反应瓶置入约120℃的油浴中，使其反应30分钟后，溶液的红色会褪去，并有大量沈淀出现，升起反应瓶待其回温，将回流管卸下且以正己烷冲洗除去瓶底中残留物中所残余的硅油。将瓶底中残留物以二氯甲烷(三次，每次50毫升)与水萃取，所得到的有机萃取液加入硫酸镁干燥后过滤、回旋浓缩抽干溶剂，粗产物以管柱层析(使用1∶3之比例之二氯甲烷及正己烷)纯化，所得产物再利用二氯甲烷与正己烷以再结晶方式进行纯化，可得到4985.3毫克以化学式12表示的固体化合物12，即3，7-二溴-5，5-螺芴基-5H-二苯并[a，d]环庚烯(3，7-dibromo-5，5-spirofluorenyl-5H-dibenzo[a，d]cycloheptene)，产率为91％。
由化学式12所表示的化合物12的核磁共振(NMR)分析资料如下：m.p.283℃(DSC)；M.W.：500.22；1H NMR(400MHz，CDCl3)δ7.90(d，J＝7.7，2H)，7.76(d，J＝7.6，2H)，7.42(t，J＝7.5，2H)，7.32(dd，J＝8.2，2.0，2H)，7.29(d，J＝7.6，2H)，7.20(d，J＝8.2，2H)，6.98(s，2H)，6.90(s，2H)；13C NMR(100MHz，CDCl3)δ151.53，143.45，138.86，135.18，133.54，132.64，131.91，130.49，128.59，127.87，126.66，122.78，120.59，65.25；MS(FAB)499.9(M+)；TLC Rf0.35(CH2Cl2/hexane，1/5)。
步骤2
取由化学式12表示的化合物2489.8毫克(5毫莫耳)与苯亚硒酸酐(BSA)2340.8毫克(6.5毫莫耳)放入反应瓶中，并加入20ml氯苯，在反应瓶上方安装回流装置，将反应瓶置入约130℃油浴中，使其反应18小时后，以薄层层析法(TLC)确定无反应起始物存在，升高反应瓶待其回温，将回流管卸下且以正己烷冲洗除去瓶底残留物所残余的硅油，利用回旋浓缩仪将氯苯从残留物抽干，加入20毫升正己烷至抽滤漏斗(内置2公分厚硅胶与滤纸)以溶解残留物中的副产物二苯基二硒醚(diphenylselenide)，并过滤以得到固体沈淀物，并以正己烷清洗固体多次，将固体刮下可直接得到粗产物，再利用二氯甲烷与正己烷以再结晶方式进行纯化，可得到2164.5毫克的以化学式13表示的固体化合物13，即螺-芴-3，7-二溴-二苯并环庚烷-10，11-二酮(spiro-fluorene-3，7-dibromo-dibenzosuberan-10，11-dione)，产率为82％，同时可回所述副产物二苯基二硒醚。
由化学式13所表示的化合物13的NMR分析资料如下：m.p.257.1℃(DSC)；M.W.：527.94；1H NMR(400MHz，CDCl3)δ7.86(d，J＝7.6，2H)，7.72(d，J＝8.3，2H)，7.49(dd，J＝8.3，1.62，2H)，7.46(t，J＝7.5，2H)，7.22(t，J＝7.7，2H)，7.29(t，J＝7.6，2H)，7.66(d，J＝7.1，2H)，6.72(s，2H)；13C NMR(100MHz，CDCl3)δ197.10，152.64，144.45，139.48，133.34，132.83，131.77，131.16，129.31，129.05，128.87，125.41，121.21，67.34；MS(FAB)529.2(M+)；TLC Rf0.3(CH2Cl2/hexane，1/3)。
步骤3
取一50毫升双颈圆底瓶，内放搅拌子，上接回流管，真空干燥后充入氮气，在氮气环境下，分别加入以化学式13表示的化合物1060毫克(2毫莫耳)、邻苯二胺(o-phenylenediamine)238毫克(2.2毫莫耳)及催化剂对甲基苯磺酸并溶于20毫升乙醇，接着开启回流装置将反应置入已预热至约80℃之油锅中使其反应12小时，待其回温后加入饱和碳酸氢钠水溶液淬息反应，使用二氯甲烷(三次，每次20毫升)萃取，所得到的萃取液依序加入硫酸镁干燥、过滤及回旋浓缩，粗产物以管柱层析(使用1：2之比例之二氯甲烷及正己烷)纯化后，得到940毫克的以化学式14所表示之化合物14，产率为78％。
由化学式14所表示的化合物14的NMR分析资料如下：m.p.298℃(DSC)；M.W.：602.32；1H NMR(400MHz，CDCl3)δ 8.27(q，J＝3.2，2H)，8.25(d，J＝8.2，2H)，7.90(q，J＝3.2，2H)，7.77(d，J＝7.6，2H)，7.58(dd，J＝8.2，1.9，2H)，7.36(t，J＝6.9，2H)，7.33(d，J＝1.9，2H)，7.07(bs，2H)，6.65(bs，2H)；13C NMR(100MHz，CDCl3)δ151.9，148.1，147.0，141.8，140.1，136.9，134.8，131.4，131.1，130.7，129.5，128.6，127.5，124.7，120.8，65.7；MS(ESI)601.0(M+H+)；TLC Rf0.40(CH2Cl2/hexanes，1/2)；HR-MS calcd for C33H18Br2N2：599.9837，found：599.9816。
步骤4
取一50毫升双颈圆底瓶并放入搅拌子并上接回流管，真空干燥后充入氮气，接着分别加入602毫克(1毫莫耳)的化合物14与35毫克(0.03毫莫耳)催化剂三苯基膦钯(Pd(PPh3)4)，接着以针筒打入20毫升1，2-二甲氧基乙烷并混合10分钟后，再加入694毫克(2.4毫莫耳)对二苯基胺基苯硼酸与0.1M碳酸钠水溶液1毫升，最后开启回流装置将反应回流12小时，待其回温后通入氧气淬息反应，以二氯甲烷(三次，每次20毫升)萃取，所得到的萃取液依序加入硫酸镁干燥、过滤及回旋浓缩，粗产物以管柱层析(以1∶1比例之二氯甲烷及己烷)纯化，得到847毫克以化学式15表示的化合物，即3，7-二(4-(N，N-二苯基氨基)-苯基)-5，5-螺芴基-二苯并-环庚烯[d]喹啉(3，7-Bis(4-(N，N-diphenylamino)-phenyl)-5，5-spirofluorenyl-dibenzo-suberene[d]quinoxaline)产率为91％
由化学式15所表示的化合物15的NMR分析资料如下：Td210℃(TgA)；Tg523℃(DSC)；M.W.：931.13；1H NMR(400MHZ，CDCl3)δ8.44(d，J＝8.2，2H)，8.31(q，J＝3.3，2H)，7.87(q，J＝3.3，2H)，7.72(d，J＝7.4，2H)，7.67(dd，J＝8.1，1.6，8H)，7.48(d，J＝1.6，2H)，7.30-7.23(m，16H)，7.09(d，J＝7.7，8H)，7.03(t，J＝8.0，10H)；13C NMR(100MHz，CDCl3)δ 152.9，149.6，147.6，147.5，146.1，141.8，141.2，140.2，136.4，133.8，133.7，130.1，129.5，129.3，128.1，127.5，127.1，126.8，125.8，124.7，123.4，123.1，120.5，66.8；MS(ESI)931.4(M+H+)；TLC Rf0.45(CH2Cl2/hexane，1/1)；HR-MS calcd for C69H46N4：930.3722，found：930.3855；Anal.Calcd for C69H46N4：C，89.00，H，4.98，N，6.02.Found：C，89.09，H，4.98，N，6.17。
得到化学式14表示的化合物之后，还可以修饰以得到各种不同的喹啉融合螺顺式二苯乙烯/芴化合物，例如合成以化学式16-18所表示之化合物16-18，其合成方法包括以下步骤。
步骤5
取50毫升双颈圆底瓶内置搅拌子与上接回流管，真空干燥后通入氮气。接着将以化学式14代表之化合物14602毫克(1毫莫耳)、双戊酰二硼(bis(pinacolato)diboron)588毫克(2.2毫莫耳)、醋酸钾409毫克(6毫莫耳)、与催化剂Pd(dppf)Cl236毫克(0.05毫莫耳)依序加入圆底瓶中，再以针筒将20mL之脱氧二氧陆环注入圆底瓶中。接着加热反应瓶使其回流反应18小时，再将反应瓶回温至室温并通入氧气以淬息反应。以二氯甲烷(三次，每次20毫升)萃取反应后之混合物，所得萃取液依序以硫酸镁干燥、以硅藻土过滤、再回旋浓缩得粗产物。接着以甲醇(三次，每次20毫升)清洗粗产物，得到408毫克(0.79毫莫耳)以化学式16代表之化合物16的白色固体，产率79％。
利用相似于上述的方法，本领域技术人士可以得到由化学式19来表示之透明结晶物质，即一关键的中间产物，其中R为H、叔丁基或萘基。
此外，本案更多的喹啉融合螺顺式二苯乙烯/芴化合物实施例可对关键的中间产物进行某些化学反应，像是铃木偶联反应(Suzuki coupling reactions)来制造。因此，像是以化学式20-23来表示的喹啉融合螺顺式二苯乙烯/芴化合物20-23：
其中R为H、叔丁基或萘基。
将7.7mmol的由化学式19所表示的化合物其中之一、16.9mmol的2-腈苯基硼酸或3-腈苯基硼酸或16.9mmol的其他类型的硼酸、985mg(0.09mmol)催化剂三苯基膦钯(Pd(PPh3)4)、以及3.3g(30.8mmol)的碳酸钠的混合物，并加入100ml甲苯、10ml乙醇以及10ml蒸馏水，在氩气的环境下加热至85℃持续24小时。然后以二氯甲烷(三次，每次20毫升)萃取反应后之混合物，所得萃取液依序以约2g的無水硫酸镁干燥、再以回旋浓缩得粗产物，粗产物以管柱层析(以2：1比例之二氯甲烷及己烷作为洗涤液)使用硅胶纯化，得到以化学式由化学式20至23表示的化合物20至23其中之一的白色固体，产率61-75％。
由化学式20所表示的化合物20的NMR分析资料如下：Tm357℃M.W.：646.75；1H NMR(400MHz，CDCl3)δ8.52(d，J＝8.0，2H)，8.34-8.32(m，2H)，7.95-7.91(m，2H)，7.77(d，J＝7.8Hz，2H)，7.71-7.63(m，4H)，7.47-7.43(m，6H)，7.10(bs，2H)，6.80(bs，2H)；13C NMR(100MHz，CDCl3)δ152.25，149.01，146.20，144.60，141.89，139.80，138.22，134.15，132.63，130.74，129.57，127.60，127.46，126.52，120.89，118.70，111.29；TLC Rf0.32(CH2Cl2/hexanes，2/1)；HRMS calcd for C47H26N4：46.2157，found：646.2149.
由化学式22所表示的化合物20的NMR分析资料如下：Tm383℃(DSC)；M.W.：600.69；1H NMR(400MHz，CDCl3)δ8.61(d，J＝4.8，4H)，8.54(d，J＝8.0，2H)，8.37-8.35(m，2H)，8.25(dd，J＝8.0，1.7，2H)，8.17(d，J＝1.6，2H)，8.07(d，J＝7.8，2H)，7.77(d，J＝7.6，2H)，7.50(d，J＝8.0，2H)，7.41(td，J＝7.5，1.0，2H)，7.11(bs，2H)，6.85(t，J＝4.8，2H)；13C NMR(100MHz，CDCl3)δ164.3，157.0，152.6，152.4，149.5，142.2，139.1，138.6，137.5，133.9，132.7，129.2，128.0，127.5，127.0，126.9，120.4，118.7，66.3；TLC Rf0.25(CH2C12/hexanes，3/1)；HR-MS(ESI)Anal.Calcd for C41H24N6：600.2062，found：600.2066.
前述化合物20至化合物23的玻璃转移温度(Tg)、热裂解温度(Td)、吸收光谱的最高波峰波长值(λmax)、以及光致发光(photoluminescence)光谱的最高波峰波长值(PL_λmax)被量测并记录于表1中。在表1中，Φ代表苯基、C代表碳、N代表氮、QS代表喹啉融合螺顺式二苯乙烯/芴结构、Py代表吡啶基、以及Pm与Pm’其中任一代表嘧啶基。
表1
由表1可知，本发明所提出的喹啉融合螺顺式二苯乙烯/芴化合物及其衍生物的玻璃转移温度范围介于165至175℃之间、以及其热裂解温度范围介于413至421℃之间，此意谓这些喹啉融合螺顺式二苯乙烯/芴化合物及其衍生物衍生物具有优秀的热稳定性，且在高电压或高电流密度操作条件下不易裂解。此外，前述化学式20～化学式23的氧化电位及还原电位可由循环伏安法(CV)来量测并记录于表2中。
表2
由表2可知，本发明所提出的喹啉融合螺顺式二苯乙烯/芴化合物及其衍生物的氧化电位介于1.25V至1.3V之间，以及所量测的还原电位介于-1.91V至-2.04V之间。
依据本发明所制作OLED装置的过程说明如下。将铝基板经清洗后，放入蒸镀机中，于真空度达约7×10-6torr以下，将下列表3中之各种有机材料及金属依序蒸镀至铝基板上，以氮气破真空后取出蒸镀好之基板以进行评估。可选择地，也可以取ITO玻璃来制作所述OLED装置。所述ITO玻璃于清洗后，放入蒸镀机中，以前述相反的顺序于所述ITO玻璃上沉积各种有机材料及金属，来得到所述OLED装置。
为了证明本发明提出的喹啉融合螺顺式二苯乙烯/芴混成材料的确能够应用作为有机发光二极管之电洞阻挡型的电子传输层及/或发光层，多个实验组及控制组的OLED装置被设计及制作，其中OLED的各层组成材料整合于表3。
表3
其中BmPyPb为1，3-二(3，5-二吡啶-3-基-苯基)苯的缩写；DPyPA为9，10-二(3-(吡啶-3-基)苯基)蒽的缩写；TPBi为1，3，5-三(1-苯基-1H-苯并咪唑-2-基)苯的缩写；NPB为N，N’-二(1-萘基)-N，N’-二苯基-(1，1’-联苯基)-4，4’-二胺的缩写；ET01为由化学式24来表示的化合物；TAPC为4，4’-亚环己基双[N，N-双(4-甲基苯)苯胺](4，4’-cyclohexylidenebis[N，N-bis(4-methylphenyl)benzenamine])的缩写；HATCN为1，4，5，8，9，11-六氮杂三伸苯基六腈(1，4，5，8，9，11-hexaazatriphenylene hexacarbonitrile)的缩写；以及绿磷光为11-(4，6-二苯基-1，3，5-三嗪-2-基)-12-苯基-11，12-二氢吲哚[2，3-a]咔唑(11-(4，6-diphenyl-1，3，5-triazin-2-yl)-12-phenyl-11，12-dihydroindolo[2，3-a]carba zole)且由化学式25来表示的化合物。
表3中的TPBi、DPyPA、BmPyPb以及ET01也作为OLED装置中的电子传输层。以上各组OLED装置的开启电压(Von)、外部量子效率(ηext)、电流效率(ηc)、功率效率(ηp)、以及最大亮度(Lmax)被量测并记录于表4。
表4
参照表4中对于绿磷光OLED装置的量测数据可以得知，相较于控制组1A、1B、1C的单一电洞传输层的OLED装置，使用单一电洞传输层的实验组1～4的OLED组件具有更优秀的ηext、ηc、ηp及Lmax，且实验组1(CNΦQSΦCN)及实验组2(PyQSPy)显示的结果最佳，其中ηext介于15.0-15.7％的范围，ηc介于54.5-55.8cd/A的范围，ηp介于64.7-70.2lm/w的范围，且Lmax介于139,200-145，320cd/m2的范围。
此外，使用单一电洞传输层的实验组5以及实验组6的OLED装置的ηext、ηc、ηp及Lmax也优于使用复合电洞传输层(即双电洞传输层)的控制组2及控制组3的OLED装置。此外，使用复合电洞传输层的实验组6(PyQSPy)的商业化OLED装置也显示优异的ηext、ηc、ηp及Lmax，优于复合电洞传输层的控制组2及控制组3的OLED装置。
还有，绿磷光OLED装置也经过基于起始亮度为1,000cd/cm2的寿命评估测试，寿命评估测试的结果显示，实验组5与实验组6的绿磷光OLED的半衰寿命(LT50)分别为15，500与16,840小时。而控制组1A与控制组3的绿磷光OLED半衰寿命则分别为1,000与13,500小时。此外，将控制组1A的绿磷光OLED中的BmPyPb替换成TmPyPb，则具有TmPyPb材料的绿磷光OLED的半衰寿命测量到仅有210小时。
经由以上的说明可知，本发明的喹啉融合螺顺式二苯乙烯/芴化合物及其衍生物已可完全地被引进用于OLED，且本发明的材料具有以下优点：(1)本发明具有氰芳基或氰杂芳基取代的喹啉融合螺顺式二苯乙烯/芴化合物及其衍生物具有介于165至175℃之间的玻璃转移温度，及介于413至421℃之间热裂解温度、可逆电子传输特性、以及平衡之电荷载子的移动性。(2)多项实验数据证明，本发明的喹啉融合螺顺式二苯乙烯/芴化合物及其衍生物的确能被使用作为OLED的电洞阻挡型的电子传输体。且实验数据亦显示使用这些喹啉融合螺顺式二苯乙烯/芴化合物及其衍生物作为电洞阻挡型的电子传输体的OLED，其外部量子效率、电流效率、功率效率、最大亮度及组件寿命，皆优于习知或已商业化的OLED。
虽然本发明已将较佳实施例揭露如上，但其并非用以限定本发明，任何熟知本领域的技术人员，在不脱离本发明的精神和范围内，可作更动与润饰。因此本发明的保护范围以后附的权利要求保护的范围为准。本案由熟悉本领域的技术人员所作的各种修饰，皆不脱离所附的权利要求的保护范围。

Claims (11)

1.一种化合物，包括：
顺式二苯乙烯段；
具有四键原子的桥接原子段，以所述四键原子的两个键连接于所述顺式二苯乙烯段，形成七员环结构段；以及
喹啉段，连接于所述顺式二苯乙烯段。
2.如权利要求1所述的化合物，其中所述喹啉段由化学式1来表示：
化学式1
以及
所述顺式二苯乙烯段由化学式2来表示：
化学式2
其中R1或R11为H、卤素、-Ar、-CN、-CF3、-Ar-F、芳香胺基、或由化学式3a、3b、3c、3d、3e、3f、3g、3h、3j、3k、3j、3m或3n来表示：
其中卤素为F、Cl、Br或I，Ar及G为苯基，以及所述芳香胺基为-NR4R5，R4或R5为H、苯基或萘基，n＝1或2，以及m＝1、2或3，所述NR4R5由化学式3p、3q或3r来表示：
其中X为H或未取代或被取代的具有1-20个碳原子的烷基。
3.如权利要求1所述的化合物，其中所述四键原子为碳或硅，所述桥接原子段以所述四键原子的另两个键的至少其中之一与甲基或苯基连接，所述桥接原子段为由化学式A1、A2、A3或A4所表示：
其中R3为H、叔丁基或萘基，所述化合物为由化学式4来表示：
化学式4。
4.如权利要求1所述的化合物，其中
所述化合物的玻璃移转温度(Tg)介于165℃至175℃之间，或热裂解温度(Td)介于413℃至421℃之间；
所述化合物的的氧化电位介于1.25V至1.30V之间，或还原电位介于-1.91V至-2.04V之间；或
所述化合物作为有机发光电子组件中的电子传输层的材料、电洞阻挡层的材料、发光材料或其组合。
5.一种电子组件，所述电子组件由化合物制成，其中所述化合物包括：
顺式二苯乙烯段；
具有四键原子的桥接原子段，以以所述四键原子的两个键连接于所述顺式二苯乙烯段，形成七员环结构段；以及
喹啉段，连接于所述顺式二苯乙烯段。
6.如权利要求5所述的电子组件，其中所述电子组件包括：
第一电极；
第二电极设置于所述第一电极对面；以及
有机层，设置于所述第一电极及所述第二电极之间；
其中所述有机层包含所述化合物。
7.如权利要求5所述的电子组件，其中所述电子组件还包括设置介于所述发光层及所述第二电极之间的电洞传输层、电子阻挡层或其组合，所述第一电极为阴极，所述第二电极为阳极，所述有机层为电子传输层、电洞阻档层、发光层或其组合，而所述电子组件为有机发光组件，当所述有机层为所述电子传输层与所述电洞阻挡层之组合时，所述有机层以单层形成。
8.如权利要求7所述的电子组件，还包括设置介于所述发光层及所述第二电极之间的电洞传输层、电子阻挡层或其组合，所述第一电极为阴极，所述第二电极为阳极，所述有机层为电子传输层、电洞阻档层、发光层或其组合，而所述电子组件为有机发光组件，当所述有机层为所述电子传输层与所述电洞阻挡层之组合时，所述有机层以单层形成，所述有机发光组件还包括设置于所述发光层及阳极之间的电洞传输层、设置于于所述电洞传输层及发光层之间的电子阻挡层、设置于于所述电子阻挡层及阳极之间的电洞注入层、以及设置于所述电子传输层与所述阴极之间的电子注入层。
9.如权利要求5所述的电子组件，其中所述的电子组件系用于有机发光装置、太阳能电池装置、有机晶体管、侦测装置、平面显示器、计算机显示屏幕、电视、告示牌、室内或室外照明、室内或室外讯号灯、可挠式显示器、激光打印机、桌上型电话、可携式电话、遥控装置、平板计算机、笔记本电脑、数字相机、摄录像机、探视器、微型显示设备、车用装置、外墙显示设备、视听屏幕、或讯号装置。
10.一种制造由化学式4来表示的化合物的方法，
化学式4，
所述方法包括：
将由化学式11来表示的化合物与酸反应。形成由化学式12来表示的化合物：
将由化学式12来表示的化合物与无水酸反应。形成由化学式13来表示的化合物：
以及
将由化学式13来表示的化合物与无水物反应。形成由化学式14来表示的化合物：
其中R为H、卤素、-Ar、-CN、-CF3、-Ar-F、芳香胺基、或由化学式3a、3b、3c、3d、3e、3f、3g、3h、3j、3k、3j、3m或3n来表示：
其中卤素为F、Cl、Br或I，Ar及G为苯基，以及所述芳香胺基为-NR4R5，R4或R5为H、苯基或萘基，n＝1或2，以及m＝1、2或3。
11.如权利要求10所述的方法，其中所述酸包括醋酸及盐酸，所述无水酸包括无水苯亚酸，而当R为芳香胺基时，所述由化学式4来表示的化合物为由化学式15来表示的化合物：
化学式15，
且所述方法还包括将由化学式4来表示的化合物与对二苯基胺基苯硼酸反应，以得到所述由化学式15来表示的化合物。
化学式4
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