CN114456076B - 芴衍生物以及包含它们的有机电致发光元件 - Google Patents
芴衍生物以及包含它们的有机电致发光元件 Download PDFInfo
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- CN114456076B CN114456076B CN202210108906.XA CN202210108906A CN114456076B CN 114456076 B CN114456076 B CN 114456076B CN 202210108906 A CN202210108906 A CN 202210108906A CN 114456076 B CN114456076 B CN 114456076B
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- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Abstract
本发明涉及有机电致发光材料技术领域，具体涉及一种如式I所示的芴衍生物以及包含它们的有机电致发光元件。本发明提供的式I所示的化合物，提高了材料热稳定性和输送载流子的能力，本发明的材料应用在有机电致发光元件中可显著降低驱动电压、提高发光效率和寿命。
Description
技术领域
本发明涉及有机电致发光材料技术领域，具体涉及一种芴衍生物及其在有机电致发光元件中的应用。
背景技术
一般而言，有机发光现象是指在对有机物质施加电能时发出光的现象。即在阳极与阴极之间配置有机层时，如果在两个电极之间施加电压，则空穴会从阳极注入至有机层，电子会从阴极注入至有机层。当所注入的空穴和电子相遇时，会形成激子，当该激子跃迁至基态时，会发出光和热。
最近几年有机电致发光显示技术己趋于成熟，一些产品已进入市场，但在产业化时程中，仍有许多问题亟待解决。特别是用于制作元件的各种有机材料，其载流子注入和传输性能、材料电发光性能、使用寿命、色纯度、各种材料之间及与各电极之间的匹配等，尚有许多问题还未解决。尤其是发光元件在发光效率和使用寿命还达不到实用化要求，这大大限制了OLED技术的发展。而利用三线态发光的金属配合物磷光材料具有高的发光效率，其绿光和红光材料已经达到使用要求，但是金属配合物磷光材料要求具有高三线态能级的磷光材料或空穴材料与之匹配，因此，开发具有高三线态能级的磷光材料或空穴材料是当前OLED发展的迫切需求。
在目前的技术发展下，无论是对于荧光材料还是对于磷光材料，特别是在用于有机电致发光元件中的工作电压、效率和寿命方面和在升华期间的热稳定性方面，都还需要改进。
由此，为了克服如上所述的以往技术问题而进一步提高有机电致发光元件的特性，继续要求对于在有机电致发光元件中可用作磷光材料或空穴材料的更加稳定且有效的物质的开发。
发明内容
本发明的目的是提供一种芴衍生物。
本发明另一个目的是提供一种含有上述芴衍生物的有机电致发光材料。
本发明还有一个目的是提供一种有机电致发光元件，以及上述芴衍生物在制备有机电致发光元件中的应用。
为实现上述目的，本发明采用如下技术方案：
一种芴衍生物，其结构式如式I所示：
其中：
Ra、Rb、Rc、Rd选自由C1～C40的烷基、C3～C40的环烷基或带有支链的烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组；
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12各自独立地选自由氢、氘、卤素、腈基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C2-C60杂环芳基或式(II)组成的群组，任意相邻的两个或多个基团可任选地接合或稠合形成另外的一个多个取代或未取代的环，在所形成的环中含有或不含有一个或多个杂原子N、P、B、O或S；
Ar2、Ar3各自独立地选自由取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组；
m选自0～5的整数；
L选自单键、取代或未取代的C6-C60的亚芳基、或者取代或未取代的C2-C60的亚杂芳基；
*—表示式(II)与式(I)的连接键。
本说明书中，相邻基团彼此结合而形成的取代或未取代的环中，“环”是指取代或未取代的烃环、或者取代或未取代的杂环。
优选地，所述Ra、Rb、Rc、Rd选自甲基、乙基、环戊基、环己基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组。
优选地，所述R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12各自独立地选自由氢、氘、取代或未取代的C6-C60芳基、取代或未取代的C2-C60杂环芳基或式(II)组成的群组。
优选地，所述Ar2、Ar3各自独立地选自由取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组。
优选地，所述m选自0、1或2。
根据本发明的实施例，所述Ra、Rb、Rc、Rd选自甲基、乙基或苯基组成的群组。
根据本发明的实施例，所述R1、R2、R3、R4各自独立地选自由氢或式(II)组成的群组，且至少有一个为式(II)基团。
根据本发明的实施例，所述R5、R6、R7、R8、R9、R10、R11、R12为氢或氘。
优选地，上述化合物中，所述L选自单键或由以下III-1～III-15所示基团组成的群组：
其中，
Z11和Z12各自独立地选自由氢、氘、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C60烷基、C2-C60烯基、C2-C60炔基、C1-C60烷氧基、C3-C60环烷烃基、C3-C60环烯烃基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫醚基、或者取代或未取代的C2-C60杂环芳基组成的群组；
Z13表示取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫醚基、或者取代或未取代的C2-C60杂环芳基中的一种或多种；
y1表示1-4的整数；y2表示1-6的整数；y3表示1-3的整数；y4表示1-5的整数；
T2表示O、S、CR’R”或NAr’；
R’、R”各自独立地选自由氢、氘、C1～C60的烷基、C1～C60的杂烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组，R’和R”可任选地接合或稠合形成另外的一个多个取代或未取代的环，在所形成的环中含有或不含有一个或多个杂原子N、P、B、O或S；优选地，R’、R”为甲基、苯基或芴基；
Ar’选自由C1～C60的烷基、C1～C60的杂烷基、C3～C60的环烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组；优选地，Ar’为甲基、乙基、苯基或萘基；
表示取代基与主体结构的连接键。
根据本发明的C6-C60芳基，特别是指衍生自如下物质的基团：苯、萘、蒽、苯并蒽、菲、芘、苝、荧蒽、并四苯、并五苯、苯并芘、联苯、偶苯、三联苯、三聚苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式或反式茚并芴、顺式或反式茚并咔唑、顺式或反式吲哚并咔唑、三聚茚、异三聚茚、螺三聚茚、螺异三聚茚、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、二苯并噻吩、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、苯并[5,6]喹啉、苯并[6,7]喹啉、苯并[7,8]喹啉、吩噻嗪、吩噁嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、噁唑、苯并噁唑、萘并噁唑、蒽并噁唑、菲并噁唑、异噁唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、六氮杂苯并菲、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、1,5-二氮杂蒽、2,7-二氮杂芘、2,3-二氮杂芘、1,6-二氮杂芘、1,8-二氮杂芘、4,5-二氮杂芘，4,5,9,10-四氮杂苝、吡嗪、吩嗪、吩噁嗪、吩噻嗪、荧红环、萘啶、氮杂咔唑、苯并咔啉、咔啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-噁二唑、1,2,4-噁二唑、1,2,5-噁二唑、1,3,4-噁二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、吲嗪、喹唑啉和苯并噻二唑或者衍生自这些体系的组合的基团。
本说明书中，“取代或未取代的”这一用语是指，被选自氢、氘、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C60烷基、C2-C60烯基、C2-C60炔基、C1-C60烷氧基、C3-C60环烷基、C3-C60环烯基、C6-C60芳基、C6-C60芳氧基、C6-C60芳硫醚基和C2-C60杂环芳基中的1个以上的取代基取代或未取代，或者被上述例示的取代基中的2个以上的取代基连接而成的取代基取代或未取代。
优选地，所述化合物为以下C01至C111组成的群组：
其中，*—T3—*选自*—O—*、*—S—*或下述结构中的一种：
*—和—*表示连接键。
本发明还提供一种材料，所述材料的原料包含上述的化合物有机电致发光材料，优选的，所述材料为空穴注入层材料、空穴传输层材料、空穴阻挡层材料、发光层材料、电子传输层材料、电子注入层材料、CPL材料或电子阻挡层材料。包含本发明的化合物的材料具有载流子传输的能力或光取出能力。
本发明还提供一种有机电致发光元件，其包含第一电极、第二电极、CPL层和置于所述第一电极、所述第二电极之间的一层以上的有机层；所述有机层或CPL中的至少一层的材料包含上述的化合物。
所述有机电致发光元件包含阴极、阳极、CPL和至少一个发光层。除了这些层之外，它还可以包含其它的层，例如在每种情况下，包含一个或多个空穴注入层、空穴传输层、空穴阻挡层、电子传输层、电子注入层、激子阻挡层、电子阻挡层和/或电荷产生层。具有例如激子阻挡功能的中间层同样可引入两个发光层之间。然而，应当指出，这些层中的每个并非必须都存在。此处所述有机电致发光元件可包含一个发光层，或者它可包含多个发光层。即，将能够发光的多种发光化合物用于所述发光层中。特别优选具有三个发光层的体系，其中所述三个层可显示蓝色、绿色和红色发光。如果存在多于一个的发光层，则根据本发明，这些层中的至少一个层包含本发明的化合物。
进一步地，根据本发明的有机电致发光元件不包含单独的空穴注入层和/或空穴传输层和/或空穴阻挡层和/或电子传输层，即发光层与空穴注入层或阳极直接相邻，和/或发光层与电子传输层或电子注入层或阴极直接相邻。
在根据本发明的有机电致发光元件的其它层中，特别是在空穴传输层中和发光层中以及在CPL中，所有材料可以按照根据现有技术通常所使用的方式来使用。本领域普通技术人员因此将能够在不付出创造性劳动的情况下与根据本发明的发光层组合使用关于有机电致发光元件所知的所有材料。
此外优选如下的有机电致发光元件，可以借助于升华方法施加一个或多个层，其中在真空升华装置中在低于10-5Pa、优选低于10-6Pa的初压下通过气相沉积来施加所述材料。然而，所述初压还可能甚至更低，例如低于10-7Pa。
同样优选如下的有机电致发光元件，也可以借助于有机气相沉积方法或借助于载气升华来施加一个或多个层，其中，在10-5Pa至1Pa之间的压力下施加所述材料。该方法的特别的例子是有机蒸气喷印方法，其中所述材料通过喷嘴直接施加，并且因此是结构化的。
此外优选如下的有机电致发光元件，从溶液中，例如通过旋涂，或借助于任何所希望的印刷方法例如丝网印刷、柔性版印刷、平版印刷、光引发热成像、热转印、喷墨印刷或喷嘴印刷，来产生一个或多个层。可溶性化合物，例如通过适当的取代式I所示的化合物获得可溶性化合物。这些方法也特别适于低聚物、树枝状大分子和聚合物。此外可行的是混合方法，其中例如从溶液中施加一个或多个层并且通过气相沉积施加一个或多个另外的层。
这些方法是本领域普通技术人员通常已知的，并且他们可以在不付出创造性劳动的情况下将其应用于包含根据本发明的化合物的有机电致发光元件。
因此，本发明还涉及制造根据本发明的有机电致发光元件的方法，包括借助于升华方法来施加至少一个层，和/或借助于有机气相沉积方法或借助于载气升华来施加至少一个层，和/或从溶液中通过旋涂或借助于印刷方法来施加至少一个层。
此外，本发明涉及包含至少一种上文指出的本发明的化合物。如上文关于有机电致发光元件指出的相同优选情况适用于所述本发明的化合物。特别是，所述化合物此外还可优选包含其它化合物。从液相处理本发明的化合物，例如通过旋涂或通过印刷方法进行处理，需要处理本发明的化合物的制剂，这些制剂可以例如是溶液、分散体或乳液。出于这个目的、可优选使用两种或更多种溶剂的混合物。合适并且优选的溶剂例如是甲苯、苯甲醚、邻二甲苯、间二甲苯或对二甲苯、苯甲酸甲酯、均三甲苯、萘满、邻二甲氧基苯、四氢呋喃、甲基四氢呋喃、四氢吡喃、氯苯、二噁烷、苯氧基甲苯，特别是3-苯氧基甲苯、(-)-葑酮、1,2,3,5-四甲基苯、1,2,4,5-四甲基苯、1-甲基萘、2-甲基苯并噻唑、2-苯氧基乙醇、2-吡咯烷酮、3-甲基苯甲醚、4-甲基苯甲醚、3,4-二甲基苯甲醚、3,5-二甲基苯甲醚、苯乙酮、α-萜品醇、苯并噻唑、苯甲酸丁酯、异丙苯、环己醇、环己酮、环己基苯、十氢化萘、十二烷基苯、苯甲酸乙酯、茚满、苯甲酸甲酯、1-甲基吡咯烷酮、对甲基异丙基苯、苯乙醚、1,4-二异丙基苯、二苄醚、二乙二醇丁基甲基醚、三乙二醇丁基甲基醚、二乙二醇二丁基醚、三乙二醇二甲基醚、二乙二醇单丁基醚、三丙二醇二甲基醚、四乙二醇二甲基醚、2-异丙基萘、戊苯、己苯、庚苯、辛苯、1,1-双(3,4-二甲基苯基)乙烷，或这些溶剂的混合物。
优选地，上述有机电致发光元件中，所述有机层包括空穴注入层、空穴传输层、空穴阻挡层、发光层、CPL层、电子传输层、电子注入层或电子阻挡层。
本发明还提供上述的化合物在制备有机电致发光元件中的应用。
另外，如无特殊说明，本发明中所用原料均可通过市售商购获得，本发明所记载的任何范围包括端值以及端值之间的任何数值以及端值或者端值之间的任意数值所构成的任意子范围。
本发明所取得的有益效果：
本发明提供的式I所示的芴衍生物，增大了芴端分子的刚性和横截面积，具有高的三线态能级，同时提高了材料热稳定性和阻挡电子的能力，本发明的材料应用在有机电致发光元件中，可显著降低驱动电压、提高发光效率和寿命。
附图说明
图1是本发明的有机电致发光元件的一个含有CPL层的示意图；
图2是本发明的有机电致发光元件的一个不含空穴阻挡层的示意图。
附图标记
图1中，100是有机电致发光元件，101是基板，102是阳极层，103是空穴注入层，104是空穴传输层，105是电子阻挡层，106是发光层，107是空穴阻挡层，108是电子传输层，109是电子注入层，110是阴极层，111是CPL层。
图2中，200是有机电致发光元件，101是基板，102是阳极层，103是空穴注入层，104是空穴传输层，105是电子阻挡层，106是发光层，107是电子传输层，108是电子注入层，109是阴极层，110是CPL层。
具体实施方式
以下结合具体实施例对本发明作进一步详细说明，但不用来限制本发明的范围。
在本发明的描述中，除非另有说明，“多个”的含义是两个或两个以上；术语“上”、“下”等指示的方位或位置关系为基于附图所示的方位或位置关系，仅是为了便于描述本发明和简化描述，而不是指示或暗示所指的装置或元件必须具有特定的方位、以特定的方位构造和操作，因此不能理解为对本发明的限制。
以下实施例中所使用的实验方法如无特殊说明，均为常规方法。以下实施例中所用的实验原料和相关设备等，如无特殊说明，均可从商业途径得到，所述百分比如无特殊说明，均为质量百分比。
下述实施例对OLED材料及元件进行性能测试的测试仪器及方法如下：
OLED元件性能检测条件：
亮度和色度坐标：使用光谱扫描仪PhotoResearch PR-715测试；
电流密度和起亮电压：使用数字源表Keithley 2420测试；
功率效率：使用NEWPORT 1931-C测试。
实施例
式I所示化合物的合成路线如下：
所用符号如上文中所定义。
实施例1
化合物C-1的制备方法，包括如下步骤：
化合物Int-1的制备：
0.26mol的1-氯-2,7-二甲氧基萘溶于1000mL干燥的THF，通入氮气保护，降温至-100℃，滴加入0.52mol的1.25M正丁基锂正己烷溶液，升温至-10℃搅拌反应2小时，降温至-78℃，滴加入0.78mol的DMF，升到室温搅拌反应2小时，滴加入200mL的3M稀盐酸水溶液，分出有机相，水相用乙酸乙酯萃取，收集有机相，干燥，减压浓缩干，过硅胶柱分离纯化，得化合物Int-1，黄色固体，收率：65％。
化合物Int-2的制备：
在氮气保护下，0.2mol的Int-1溶于1000mL的二氯甲烷，降温至0℃，滴加入0.48mol的三溴化硼，搅拌反应2小时，加入500mL饱和盐水溶液，分出有机相，水相用二氯甲烷萃取，有机相干燥，过滤，减压浓缩干，用硅胶柱分离纯化，得到黄色固体Int-2，收率：86％。
化合物Int-3的制备：
在氮气保护下，50.0mmol的中间体Int-2溶于250mL的二氯甲烷，降温至0℃，加入150.0mmol的吡啶，滴加入120.0mmol的三氟甲烷磺酸酐，升到室温搅拌反应12小时，滴加入100mL的2M稀盐酸，分出有机相，水相用二氯甲烷萃取，有机相干燥，减压浓缩干，用硅胶柱分离纯化，得化合物Int-3，黄色固体，收率：92％。
化合物Int-4的制备：
在氮气保护下，24.0mmol的苯硼酸溶解于60mL的甲苯中，加入10.0mmol的化合物Int-3、96.0mmol的无水碳酸钠、0.02mmol的Pd(PPh3)4催化剂，再加入40mL的乙醇和40mL的水，升温至回流搅拌反应10小时，降到室温，加入50mL的水稀释，用乙酸乙酯萃取，收集有机相，干燥，过滤，滤液减压浓缩干，用硅胶柱分离纯化，得到黄色固体Int-4，收率84％。
化合物Int-5的制备：
在氮气保护下，20.0mmol的Int-4溶解于120mL干燥的THF中，降温至0℃，滴加入50.0mmol的1M甲基溴化镁THF溶液，升到室温搅拌反应10小时，加入50mL的2M稀盐酸，分出有机相，水相用乙酸乙酯萃取，有机相干燥，减压浓缩干，用硅胶柱分离纯化，得化合物Int-5，白色固体，收率：94％。
化合物Int-6的制备：
20.0mmol的Int-5溶解于500mL干燥的二氯甲烷中，降温至5℃，加入20.0g的分子筛和48.0mmol的氯铬酸吡啶盐，搅拌反应5小时，过滤，滤液内加入100mL的2M稀盐酸，分出有机相，再用水洗、饱和碳酸氢钠水溶液洗，有机相干燥，减压浓缩干，用硅胶柱分离纯化，得化合物Int-6，白色固体，收率：100％。
化合物C-1的制备：
在氮气保护下，20.0mmol的Int-6溶解于100mL干燥的THF中，降温至0℃，滴加入48.0mmol的1M甲基溴化镁THF溶液，升到室温搅拌反应10小时，加入50mL的2M稀盐酸，分出有机相，水相用乙酸乙酯萃取，有机相干燥，减压浓缩干，加入150mL干燥的二氯甲烷搅拌溶解，滴加入50.0mmol的三氟化硼乙醚溶液，搅拌反应12小时，加入50mL饱和的碳酸钠水溶液，分出有机相，水相用二氯甲烷萃取，有机相干燥，减压浓缩干，用硅胶柱分离纯化，得化合物C-1，白色固体，收率：77％，GC-MS(EI)：394.15、395.15。
参照上述的类似的合成方法，制备以下化合物：
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实施例2
化合物C19的制备：
12.0mmol的C-1溶解于60mL的二甲苯中，在氮气保护下，加入10.0mmol的二芳基胺、18.0mmol的叔丁醇钠、0.1mmol的碘化亚铜、0.1mmol的Pd2(dba)3催化剂，再加入0.2mmol的Xantphos，升温至110℃搅拌反应16小时，降到室温，加入20mL的水稀释，用甲苯萃取，收集有机相，干燥，过滤，滤液减压浓缩干，用硅胶柱分离纯化，得到化合物C19；
T3为CMe2，收率：78％，真空升华后，HPLC：99.95％，MS(MALDI-TOF)：m/z＝720.3644[M+H]+；1HNMR(δ、CDCl3)：8.37(1H,s)；8.27(1H,s)；8.13(1H,s)；8.05(1H,s)；7.93～7.90(3H,t)；7.62～7.58(4H,m)；7.51～7.27(11H,m)；7.24(1H,s)；7.17～7.06(4H,m)；1.81(6H,s)；1.74(6H,s)；1.67(6H,s)。
T3为NPh，收率：76％，真空升华后，HPLC：99.96％，MS(MALDI-TOF)：m/z＝769.3596[M+H]+；1HNMR(δ、CDCl3)：8.38(1H,s)；8.17～8.11(2H,m)；8.05(1H,s)；7.93(2H,s)；7.62～7.57(4H,m)；7.55～7.49(5H,m)；7.44～7.27(11H,m)；7.25～7.17(5H,m)；7.15～7.12(1H,m)；1.81(6H,s)；1.74(6H,s)。
参照上述类似的合成方法，制备以下化合物：
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实施例3
化合物C73的制备：
在氮气保护下，10.0mmol的C-1溶解于40mL的甲苯中，加入12.0mmol的芳基硼酸频哪醇酯或芳基硼酸、30.0mmol的无水碳酸钾、0.1mmol的碘化亚铜、0.01mmol的Pd132催化剂，再加入20mL的乙醇和20mL的水，升温回流搅拌反应16小时，降到室温，加入50mL的水稀释，用乙酸乙酯萃取，收集有机相，干燥，过滤，滤液减压浓缩干，用硅胶柱分离纯化，得到化合物C73；
T3为O，收率：86％，真空升华后，HPLC：99.96％，MS(MALDI-TOF)：m/z＝770.3433[M+H]+；1HNMR(δ、CDCl3)：8.25～8.20(3H,m)；8.09(1H,s)；7.98～7.93(1H,m)；7.89～7.78(6H,m)；7.56～7.48(7H,m)；7.39～7.25(10H,m)；7.08～7.04(2H,m)；7.00～6.97(1H,m)；1.81(6H,s)；1.78(6H,s)。
T3为NPh，收率：85％，真空升华后，HPLC：99.94％，MS(MALDI-TOF)：m/z＝845.3903[M+H]+；1HNMR(δ、CDCl3)：8.54～8.51(1H,m)；8.24～8.21(3H,m)；8.08(1H,s)；7.97～7.88(3H,m)；7.79～7.71(4H,m)；7.65～7.49(11H,m)；7.36～7.28(7H,m)；7.23～7.15(3H,m)；7.07～7.02(2H,m)；6.98～6.95(1H,m)；1.80(6H,s)；1.78(6H,s)。
参照上述的类似的合成方法，制备以下化合物：
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实施例4
一种有机电致发光元件200，其结构如图2所示，包括基板101、设于基板101上的阳极层102、设于阳极层102上的空穴注入层103、设于空穴注入层103上的空穴传输层104、设于空穴传输层104上的电子阻挡层105、设于电子阻挡层105上的发光层106、设于发光层106上的电子传输层107、设于电子传输层107上的电子注入层108、设于电子注入层108上的阴极层109，以及设于阴极层之上的CPL层110，其制备包括如下步骤：
1)将涂布了ITO导电层的玻璃基片在清洗剂中超声处理30分钟，在去离子水中冲洗，在丙酮/乙醇混合溶剂中超声30分钟，在洁净的环境下烘烤至完全干燥，用紫外光清洗机照射10分钟，并用低能阳离子束轰击表面。
2)把上述处理好的ITO玻璃基片置于真空腔内，抽真空至1×10-5～9×10-3Pa，在上述ITO膜上蒸镀金属铝作为阳极层，蒸镀膜厚为蒸镀化合物HI01作为空穴注入层，蒸镀膜厚为/>
3)在上述空穴注入层上继续蒸镀化合物HTM为空穴传输层，蒸镀膜厚为
4)在上述空穴传输层上继续蒸镀本发明式I所示的化合物为电子阻挡层，蒸镀膜厚为
5)在电子阻挡层上继续蒸镀PHT为主体材料和GD110为掺杂材料，GD110为mCBP质量的5％，作为有机发光层，蒸镀膜厚为
6)在有机发光层上继续蒸镀一层LiQ和ET06作为电子传输层，LiQ和ET06的质量比为50:50，蒸镀膜厚为
7)在电子传输层之上继续蒸镀一层LiF为电子注入层，蒸镀膜厚为
8)在电子注入层之上蒸镀金属镁和银作为透明阴极层，镁和银的质量比为1:2，蒸镀膜厚为
9)在透明阴极层之上再蒸镀一层NPB作为元件的CPL层，蒸镀膜厚为得到本发明提供的OLED元件。
实施例4中使用的化合物HI01、HTM、PHT、GD110、ET06和LiQ的结构如下：
实施例5
一种有机电致发光元件100，其结构如图1所示，包括基板101、设于基板101上的阳极层102、设于阳极层102上的空穴注入层103、设于空穴注入层103上的空穴传输层104、设于空穴传输层104上的电子阻挡层105、设于电子阻挡层105上的发光层106、设于发光层106上的空穴阻挡层107、设于空穴阻挡层107上的电子传输层108、设于电子传输层108上的电子注入层109、设于电子注入层109上的阴极层110，以及设于阴极层110之上的CPL层111。
对比例1
按照与实施例4相同的步骤，将步骤4)中的式I所示的化合物替换为B-1，得到对比元件1；
对比例2
按照与实施例4相同的步骤，将步骤4)中的式I所示的化合物替换为B-2，得到对比元件2；
对比例3
按照与实施例4相同的步骤，将步骤4)中的式I所示的化合物替换为B-3，得到对比元件3；
所得元件的性能检测数据以对比元件1为基准进行归一化处理，其结果列于表1中，其中驱动电压、发光效率和半峰宽(FWHM)是在元件的电流密度为10mA/cm2条件下得出，元件的LT95％寿命是在电流密度为50mA/cm2的起始条件下测得。
表1，元件性能结果
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由表1可知，本发明的芴衍生物作为电子阻挡材料制备成的发光元件同样在10mA/cm2条件下，驱动电压相较B-1、B-2、B-3降低，尤其是化合物C93(T3为NPh)驱动电压较B-1降低11％；而化合物C29(T3为NPh)发光效率较B-1提高12％，驱动电压降低9％，表现出优异的发光性能，在电流密度为50mA/cm2起始条件下的LT95％寿命有明显优势。说明本发明所公开的化合物由于在中间萘环上引入了具有强供电子基的芳胺基，与对比例的化合物相比获得了更优异的载流子平衡能力。本发明的化合物用作电子阻挡材料表现的性能能证明本发明的化合物是一类优秀的空穴材料。
虽然，上文中已经用一般性说明、具体实施方式及试验，对本发明作了详尽的描述，但在本发明基础上，可以对其作一些修改或改进，这对本领域技术人员而言是显而易见的。因此，在不偏离本发明精神的基础上所做的这些修改或改进，均属于本发明要求保护的范围。
Claims (6)
1.一种芴衍生物，其特征在于，所述芴衍生物的结构式选自由以下C01至C111组成的群组：
其中，*—T3—*选自*—O—*、*—S—*或下述结构中的一种：
*—和—*表示连接键。
2.一种有机电致发光材料，其特征在于，所述有机电致发光材料的原料包含权利要求1所述的化合物。
3.一种有机电致发光元件，其特征在于，包含第一电极、第二电极、CPL层和置于所述第一电极、所述第二电极之间的一层以上的有机层；所述有机层的材料包含权利要求1所述的化合物。
4.根据权利要求3所述的有机电致发光元件，其特征在于，所述有机层包括空穴注入层、空穴传输层、空穴阻挡层、发光层、电子传输层、电子注入层、CPL层或电子阻挡层。
5.权利要求1所述的化合物在有机电致发光元件中的应用，其特征在于，将所述化合物用于所述有机电致发光元件的空穴传输层、空穴阻挡层、发光层、电子传输层、电子注入层、CPL层或电子阻挡层。
6.一种消费型产品，其包含有机电致发光元件，所述有机电致发光元件包含：第一电极、第二电极和置于所述第一电极、所述第二电极之间的有机层，其中所述有机层包含化合物，所述化合物包含权利要求1所述的化合物。
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