CN113912471B - 蒽衍生物、有机电致发光材料、发光装置及消费型产品 - Google Patents

蒽衍生物、有机电致发光材料、发光装置及消费型产品 Download PDF

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CN113912471B
CN113912471B CN202111228751.5A CN202111228751A CN113912471B CN 113912471 B CN113912471 B CN 113912471B CN 202111228751 A CN202111228751 A CN 202111228751A CN 113912471 B CN113912471 B CN 113912471B
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organic electroluminescent
layer
light
organic
anthracene derivative
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CN113912471A (zh
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曹建华
张海威
郭文龙
边坤
唐怡杰
刘殿君
王振宇
何连贞
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Shanghai 800 Million Spacetime Advanced Material Co ltd
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Abstract

本发明涉及一种蒽衍生物、有机电致发光材料、发光装置及消费型产品，本发明所述的蒽衍生物，所述的蒽衍生物具备蒽与联苯构成七元环非平面结构的新型有机电致发光化合物，七元环蒽衍生物增大了分子位阻、阻碍有机分子间激‑激复合物的生成、提高内量子效率，并且具有与现有化合物相比更短的发光波长，由此得以提高包含该化合物的有机电致发光器件的效率和寿命；此外，该化合物改善对溶液的溶解度而解决以往蓝光材料所具有的工序的生产性以及费用问题。

Description

蒽衍生物、有机电致发光材料、发光装置及消费型产品
技术领域
本发明属于有机电致发光技术领域，具体涉及一种蒽衍生物、有机电致发光材料、发光装置及消费型产品。
背景技术
有机电致发光元件所使用的物质大部分为纯有机物或有机物与金属形成络合物的有机金属络合物，根据用途可区分为空穴注入物、空穴输送物、发光物、电子输送物、电子注入物等。在此，作为空穴注入物或空穴输送物主要使用离子化能相对较小的有机物，作为电子注入物或电子输送物主要使用电负性较大的有机物。此外，作为发光辅助层所使用的物质最好能满足如下特性。
第一、有机电致发光元件中所使用的物质需较好的热稳定性，其原因是在有机电致发光元件内部因电荷的迁移而发生焦耳热，目前，作为空穴输送层通常所使用的材料的玻璃化温度低，因此在低温下驱动时出现因发生结晶化而引起发光效率降低的现象。第二、为了降低驱动电压，需要与阴极和阳极邻接的有机物设计成电荷注入势垒较小，电荷迁移率高。第三、电极和有机层的界面、有机层和有机层的界面上一直存在能量壁垒而不可避免地累积一些电荷，因此需要使用电化学稳定性优异的物质。
发光层由主发光体和掺杂物这两种物质构成，掺杂物需要量子效率高，与掺杂物相比主发光体需要能隙大而容易发生向掺杂物的能量转移。用于电视、移动设备等的显示器根据红色、绿色、蓝色这三原色实现全彩色，发光层分别由红色主发光体/掺杂物、绿色主发光体/掺杂物以及蓝色主发光体/掺杂物构成。目前蓝光材料仍然存在发光量子效率低、色纯度差的问题。造成这种状况的主要原因是因为蓝光来自于能隙较宽的能级间的跃迁，而宽禁带的有机化合物在进行分子设计时存在一定的困难，其次蓝光材料的体系中存在着较强的π-π键相互作用，有着很强的电荷转移特性，从而使宽带隙中存在更多的无辐射弛豫通道，加剧了分子之间荧光淬灭，降低了蓝光体系的量子产率。
鉴于以上原因，特提出本发明。
发明内容
为了解决现有技术存在的以上问题，本发明提供了一种蒽衍生物、有机电致发光材料、发光装置及消费型产品，本发明所述的蒽衍生物发光为蓝色至深蓝色且发光效率高。
本发明的第一目的，提供了一种蒽衍生物。
本发明的第二目的，提供了一种有机电致发光材料。
本发明的第三目的，提供了一种有机电致发光装置。
本发明的第四目的，提供了一种消费型产品。
为了实现上述目的，本发明采用如下技术方案：
一种蒽衍生物，所述的蒽衍生物的结构通式如式(I)所示：
Figure BDA0003315206340000021
其中，R1～R15各自相同或不同地选自由氢、氘、具有C1-C40的直链烷基、具有C1-C40的直链杂烷基、具有C3-C40的支链或环状的烷基、具有C3-C40的支链或环状的杂烷基、具有C2-C40的烯基或炔基、具有5～80个，优选5～60个碳原子的芳族或芳族环系或具有2～60个碳原子的杂芳族或杂芳族环系组成的群组，R1～R8或R9～R15中任意相邻的两个或多个基团可以彼此任意的环合或稠合形成环，且R1～R15基团中的每个基团可被一个或多个基团R取代；
Ar1选自由氢、氘、具有5～80个，优选5～60个碳原子的芳族或芳族环系或具有2～60个碳原子的杂芳族或杂芳族环系组成的群组，所述环系可被一个或多个基团R取代；
所述R在每次出现时相同或不同地选自氢原子、氘原子、卤素原子、腈基、硝基、N(Ar2)2、N(R16)2、C(＝O)Ar2、C(＝O)R16、P(＝O)(Ar2)2、具有C1-C40的直链烷基、具有C1-C40的直链杂烷基、具有C3-C40的支链或环状的烷基、具有C3-C40的支链或环状的杂烷基、具有C2-C40的烯基或炔基、具有5至80个碳原子的芳族或芳族环系、杂芳族或杂芳族环系、优选5至60个碳原子的芳族或芳族环系、杂芳族或杂芳族环系、具有5至60个碳原子的芳氧基或杂芳氧基组成的组，所述R基团中的每个基团可被一个或多个基团R16取代，或这些体系的组合，其中一个或多个非相邻的-CH2-基团可被R16C＝CR16、C≡C、Si(R16)2、Ge(R16)2、Sn(R16)2、C＝O、C＝S、C＝Se、C＝NR16、P(＝O)(R16)、SO、SO2、NR16、O、S或CONR16代替，并且其中一个或多个氢原子被氘原子、卤素原子、腈基或硝基代替，其中两个或更多个相邻的R可以任选地接合或稠合形成单环或多环的脂族、芳族或芳族环系、杂芳族或杂芳族环系，所述环系可被一个或多个基团R16取代；
Ar2在每次出现时相同或不同地为具有5～60个碳原子的芳族或芳族环系或具有2～60个碳原子的杂芳族或杂芳族环系，所述环系可被一个或多个非芳族基团R16取代；并且两个Ar2基团也可通过单键或N(R16)、C(R16)2、氧或硫的桥连基彼此桥连；
R16选自由氢原子、氘原子、氟原子、腈基、具有C1-C20的脂族烃基、具有5～30个碳原子的芳族或芳族环系或具有2～60个碳原子的杂芳族或杂芳族环系组成的群组，其中一个或多个氢原子可被氘原子、卤素原子、或腈基代替，其中两个或更多个相邻的R16可彼此形成单环或多环的脂族、芳族或芳族环系、杂芳族或杂芳族环系。
本发明意义上的芳基含有5-60个碳原子，在本发明意义上的杂芳基含有2-60个碳原子和至少一个杂原子，其条件是碳原子和杂原子的总和至少是5；所述杂原子优选选自N、O或S。此处的芳基或杂芳基被认为是指简单的芳族环，即苯、萘等，或简单的杂芳族环，如吡啶、嘧啶、噻吩等，或稠合的芳基或杂芳基，如蒽、菲、喹啉、异喹啉等。通过单键彼此连接的芳族环，例如联苯，相反地不被称为芳基或杂芳基，而是称为芳族环系或杂芳族环系。
在本发明意义上的芳族环系或杂芳族环系旨在被认为是指不必仅含有芳基或杂芳基的体系，而是其中多个芳基或杂芳基还可以由非芳族单元例如C、N、O或S原子连接。因此，例如，和其中两个或更多个芳基被例如短的烷基连接的体系一样，诸如芴、9,9’-螺二芴、9,9-二芳基芴，三芳基胺、二芳基醚等的体系也被认为是指在本发明意义上的芳族环系或杂芳族环系。
本发明中使用的烷基是指碳原子数从1至40的直链或支链的饱和烃去除一个氢原子而得到的一价官能团。作为其非限制性例子，有甲基、乙基、丙基、异丁基、仲丁基、戊基、异戊基、己基等。杂烷基是指烷基上的氢原子或-CH2-被至少一个杂原子取代，所述杂原子选自卤素、腈基、N、O、S或硅，作为非限制性的例子，有二氟甲基、三氟甲基、三氟乙基、五氟乙基、腈基、乙腈基、甲氧基甲基、甲氧基乙基、三甲基硅基、三异丙基硅基等。
本发明中使用的烯基是指从具有一个以上碳碳双键的碳原子数从2至40的直链或支链的不饱和烃去除一个氢原子而得到的一价官能团。作为其非限制性例子，有乙烯基、烯丙基、异丙烯基、2-丁烯基等。
本发明中使用的炔基是指具有一个以上碳碳三键的碳原子数从2至40的直链或支链的不饱和烃去除一个氢原子而得到的一价官能团。作为其非限制性例子，有乙炔基、2-丙炔基等。
一般来说，根据本发明的环烷基、环烯基是指碳原子数从3至40的单环或多环非芳族烃去除一个氢原子而得到的一价官能团。作为其非限制性例子，有环丙基、环丁基、环戊基、环己基、降冰片基、金刚烷基、环丁烯基、环戊烯基、环己烯基、环庚基、环庚烯基，其中一个或多个-CH2-基团可被上述基团代替；此外，一个或多个氢原子还可被氘原子、卤素原子或腈基代替。
本发明中使用的杂环烷基是指原子核数从3至40的非芳香族烃去除一个氢原子而得到的一价官能团。此时，环中一个以上的碳、优选为1至3个碳被诸如N、O或S之类的杂原子取代。作为其非限制性例子，有四氢呋喃、四氢噻吩、吗啉、哌嗪等。
本发明中使用的烷氧基是指RO-所表示的一价官能团，上述R是碳原子数从1至40个的烷基，可以包含直链、支链或环结构。作为这样的烷氧基的非限制性例子，可以举出甲氧基、乙氧基、正丙氧基、1-丙氧基、叔丁氧基、正丁氧基、戊氧基、环戊氧基、环己氧基等。
本发明中使用的芳氧基是指R'O-所表示的一价官能团，上述R'是碳原子数从6至60的芳基。作为这样的芳氧基的非限制性例子，有苯氧基、萘氧基、联苯氧基等。
根据本发明的芳族或杂芳族，在每种情况下芳族或杂芳族环的原子还可被上述R16基团取代的芳族环系或杂芳族环系，特别是指衍生自如下物质的基团：苯、萘、蒽、苯并蒽、菲、芘、
Figure BDA0003315206340000051
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、吲嗪和苯并噻二唑或者衍生自这些体系的组合的基团。
进一步的，所述R1～R15各自相同或不同地选自由氢、氘、具有C1-C40的直链烷基、具有C1-C40的直链杂烷基、具有C3-C40的支链或环状的烷基、具有C3-C40的支链或环状的杂烷基、具有5～60个碳原子的芳族或芳族环系或具有2～60个碳原子的杂芳族或杂芳族环系组成的群组，R1～R8或R9～R15中任意相邻的两个或多个基团可以彼此任意的环合或稠合形成环；
Ar1选自由氢、氘、具有5～60个碳原子的芳族或芳族环系、或具有2～60个碳原子的杂芳族或杂芳族环系组成的群组。
进一步的，所述杂芳族环系是由II-1～II-17所示基团与芳族环系组成的群组，II-1～II-17具体结构如下：
Figure BDA0003315206340000061
其中，Z1、Z2各自独立地选自由氢、氘、卤素、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-C40烷基、C2-C40烯基、C2-C40炔基、C1-C40烷氧基、C3-C40环烷烃基、C3-C40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杂芳基组成的群组；
x1表示1-4的整数；x2表示1-3的整数；x3表示1或2；x4表示1-6的整数；x5表示1-5的整数；
T1表示氧原子或硫原子；
Figure BDA0003315206340000071
表示取代基与主体结构的连接键。
本发明中所述取代的C6-C60的芳基、取代的C6-C60芳氧基、取代的C6-C60芳硫醚基、取代的C2-C60的杂芳基等，所述的取代基选自由氢、氘、卤素、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-C40烷基、C2-C40烯基、C2-C40炔基、C1-C40烷氧基、C3-C40环烷烃基、C3-C40环烯基、C6-C60芳基、C6-C60芳氧基、C6-C60芳硫醚基、或者C2-C60杂环芳基组成的群组。
如本文所使用，“其组合”或“群组”表示适用清单的一或多个成员被组合以形成本领域普通技术人员能够从适用清单中设想的已知或化学稳定的布置。举例来说，烷基和氘可以组合形成部分或完全氘化的烷基；卤素和烷基可以组合形成卤代烷基取代基，例如三氟甲基等；并且卤素、烷基和芳基可以组合形成卤代芳烷基。
进一步的，所述的蒽衍生物为以下CJHB751～CJHB879结构中的一种：
Figure BDA0003315206340000072
Figure BDA0003315206340000081
Figure BDA0003315206340000091
Figure BDA0003315206340000101
Figure BDA0003315206340000111
Figure BDA0003315206340000121
Figure BDA0003315206340000131
一种有机电致发光材料，所述的有机电致发光材料包括所述的蒽衍生物。
有机电致发光材料可以单独使用本发明的化合物构成，也可以同时含有其他化合物。
本发明的有机电致发光材料中所含有的本发明的化合物可以用作但不限于发光层材料、载流子传输层材料或光折射层材料。
一种有机电致发光装置，所述的有机电致发光装置包括第一电极、第二电极和置于所述的第一电极和所述的第二电极之间的至少一层有机层，所述的有机层包含本发明提供的蒽衍生物。
所述有机电致发光装置包含阴极、阳极和至少一个发光层。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装置可包含一个发光层，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。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装置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装置的其它层中，特别是在空穴注入和空穴传输层中以及在电子注入和电子传输层中，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装置，其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器件，其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汽喷印方法，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装置，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装置的方法，其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装置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。从液相处理根据本发明的化合物，例如通过旋涂或通过印刷方法进行处理，需要根据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。
进一步的，所述有机层选自电子注入层、电子输送层、空穴阻挡层、电子阻挡层、空穴输送层、空穴注入层和发光层中的一种或几种。
进一步的，所述电子输送层、发光层包含本发明的蒽衍生物。
进一步的，所述发光层包括掺杂物和发光主体，所述掺杂物包括由蒽、萘、蒽、芘、苝、菲、荧蒽、
Figure BDA0003315206340000161
苯并蒽、芴、螺芴和并五苯及其衍生物组成的群组；所述发光主体包含本发明的蒽衍生物。
进一步的，所述的掺杂物与发光主体的质量比为1:99～50:50。
一种由所述的有机电致发光装置制成的消费型产品，所述消费型产品包括本发明提供的有机电致发光装置。
本发明中所述的消费型产品可以是以下产品中的一种：平板显示器、计算机监视器、医疗监视器、电视机、告示牌、用于内部或外部照明和/或发信号的灯、平视显示器、全透明或部分透明的显示器、柔性显示器、激光打印机、电话、蜂窝电话、平板电脑、平板手机、个人数字助理(PDA)、可佩戴装置、膝上型计算机、数码相机、摄像机、取景器、对角线小于2英寸的微型显示器、3-D显示器、虚拟现实或增强现实显示器、交通工具、包含多个平铺在一起的显示器的视频墙、剧院或体育馆屏幕、光疗装置和指示牌。
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。
与现有技术相比，本发明的有益效果为：
本发明所述的蒽衍生物具备蒽与联苯构成七元环非平面结构的新型有机电致发光化合物，七元环蒽衍生物增大了分子位阻、阻碍有机分子间激-激复合物的生成、提高内量子效率，并且具有与现有化合物相比更短的发光波长，由此得以提高包含该化合物的有机电致发光器件的效率和寿命；此外，该化合物改善对溶液的溶解度而解决以往蓝光材料所具有的工序的生产性以及费用问题，并且在原有的工序中不是其蒸镀工序而是在其溶液工序中也可以用于制备发光层。
附图说明
为了更清楚地说明本发明实施例或现有技术中的技术方案，下面将对实施例或现有技术描述中所需要使用的附图作简单地介绍，显而易见地，下面描述中的附图仅仅是本发明的一些实施例，对于本领域普通技术人员来讲，在不付出创造性劳动的前提下，还可以根据这些附图获得其他的附图。
图1是本发明的有机电致发光装置的一个底部发光例子的示意图；
图2是本发明的有机电致发光装置的一个顶部发光例子的示意图。
附图标记
1-基板、2-阳极层、3-空穴注入层、4-空穴传输层/电子阻挡层、5-发光层、6-空穴阻挡/电子传输层、7-电子注入层、8-阴极层。
具体实施方式
为使本发明的目的、技术方案和优点更加清楚，下面将对本发明的技术方案进行详细的描述。显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动的前提下所得到的所有其它实施方式，都属于本发明所保护的范围。
本发明中，制备方法如无特殊说明则均为常规方法。所用的原料如无特别说明均可从公开的商业途径获得，所述百分比如无特殊说明均为质量百分比。本发明提供的一系列新型有机化合物，所有的反应都是在众所周知的适合条件下进行，有些涉及到简单的有机制备，例如N,N-二苯胺衍生物的制备均能通过熟练的操作技能合成，在本发明中没有详细描述。
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PhotoResearchPR-715测试；
电流密度和起亮电压：使用数字源表Keithley2420测试；
功率效率：使用NEWPORT1931-C测试；
寿命测试：使用LTS-1004AC寿命测试装置。
实施例1
中间体A1的制备：
中间体A1的制备方法，包括如下步骤：
第一步：化合物Int.-1的制备
Figure BDA0003315206340000182
在氮气保护下，50.0mmol的邻碘溴苯溶于100mL干燥的四氢呋喃中，降温至0℃，滴加入52.0mL的1M异丙基溴化镁THF溶液，搅拌反应1小时，滴加入48.0mmol的9H-三苯并[a,c,e][7]环轮烯-9-酮(CAS:68089-73-6)溶于THF的溶液，升到室温搅拌反应2小时，加入50mL的2N稀盐酸水溶液，用乙酸乙酯萃取，收集有机相，干燥，过滤，滤液减压浓缩干燥，用硅胶柱分离纯化，得到中间体Int.-1，收率94％。
第二步：化合物Int.-2的制备
Figure BDA0003315206340000181
在氮气保护下，40.0mmol第一步制备的Int.-1溶解于100mL的二氯甲烷中，加入80.0mmol的三乙基硅烷，降温到0℃，缓慢滴加入30mL的三氟乙酸，升到室温搅拌反应12小时，加入50mL的水，用二氯甲烷萃取，收集有机相干燥，过滤，滤液减压浓缩干燥，用硅胶柱分离纯化，得到Int.-2，收率82％。
第三步：化合物Int.-3的制备
Figure BDA0003315206340000191
取50.0mmol第二步制备的中间体Int.-2溶解于120mL干燥的THF中，在氮气保护下，降温至-78℃，滴加入22.0mL的2.5M正丁基锂正己烷溶液，搅拌反应1小时，滴加入75.0mmol的DMF，升到室温，搅拌反应1小时，加入50mL的2N稀盐酸水溶液，分出有机相，水相再用二氯甲烷萃取，收集有机相干燥过滤，滤液减压浓缩干燥，用硅胶柱分离纯化，得到Int.-3，收率87％。
第四步：化合物Int.-4的制备
Figure BDA0003315206340000192
在氮气保护下，40.0mmol的中间体Int.-3溶于80mL的二氯甲烷中，加入8.0mmol的三氟化硼乙醚溶液，室温搅拌反应1小时，减压浓缩干燥，用硅胶柱分离纯化，得到中间体Int.-4，收率92％。
第五步：化合物A1的制备
Figure BDA0003315206340000201
41.2mmol的中间体Int.-4溶于120mL的二氯甲烷中，冰水浴降温至0℃，加入4.1mmol的对甲苯磺酸，分批加入42.0mmol的NBS，搅拌反应2小时，加入100mL的10％碳酸氢钠水溶液，分出有机相，用水洗，收集有机相，干燥，过滤，滤液减压浓缩干燥，用硅胶柱分离纯化，得到中间体A1，收率96％。
参照上述的合成方法，制备以下化合物：
Figure BDA0003315206340000202
Figure BDA0003315206340000211
实施例2
化合物CJHB761的制备：
Figure BDA0003315206340000212
取15.0mmol中间体A1与60mL的甲苯混合，在氮气保护下，加入18.0mmol的(4-(2-萘基)苯基)硼酸、54.0mmol的无水碳酸钠和173.0mg的Pd(PPh3)4催化剂，再加入30mL的乙醇和30mL的水，升温至回流搅拌反应12小时，冷却到室温，过滤，滤饼用水洗、乙醇洗，用硅胶柱分离纯化，得到白色固体CJHB761，收率84％。EI-MS/FAB,m/e:530.76，计算值：530.20。
参照上述的合成方法，制备以下化合物：
Figure BDA0003315206340000213
Figure BDA0003315206340000221
Figure BDA0003315206340000231
Figure BDA0003315206340000241
Figure BDA0003315206340000251
Figure BDA0003315206340000261
Figure BDA0003315206340000271
Figure BDA0003315206340000281
实施例3
化合物CJHB775的制备方法，包括如下步骤：
第一步：化合物Int.-5的制备
Figure BDA0003315206340000282
在氮气保护下，50.0mmol的A1溶解于120mL干燥的THF中，降温到-100℃，滴加入24mL的2.5M正丁基锂正己烷溶液，搅拌反应30分钟，滴加入75.0mmol的硼酸三异丁酯，搅拌反应30分钟，升温到-70℃反应1小时，滴加入50mL的2N稀盐酸水溶液，搅拌30分钟，分出有机相，水相用乙酸乙酯萃取，收集有机相，干燥，过滤，滤液减压浓缩干燥，加入石油醚分散，过滤，得到Int.-5，收率85％。
第二步：化合物CJHB775的制备
Figure BDA0003315206340000283
取12.0mmol中间体Int.-5与60mL的甲苯混合，在氮气保护下，加入10.0mmol的2-氯-4,6-二苯基-1,3,5-三嗪、48.0mmol的水合磷酸钾和11.0mg的Pd132催化剂，再加入30mL的乙醇和30mL的水，升温至回流搅拌反应12小时，冷却到室温，过滤，滤饼用水洗、乙醇洗，用硅胶柱分离纯化，得到白色固体CJHB775，收率76％。EI-MS/FAB,m/e:559.69，计算值：559.20。
参照上述的合成方法，制备以下化合物：
Figure BDA0003315206340000284
Figure BDA0003315206340000291
实施例4
化合物CJHB805的制备：
Figure BDA0003315206340000292
将10.0mmol的中间体A1分散在80mL的甲苯中，加入12.0mmol的N-苯基-[1,1'-联苯基]-4-胺，再加入20.0mmol的叔丁醇钠、0.05mmol的Pd2(dba)3CHCl3催化剂和0.01mL的10％叔丁基磷甲苯溶液，升温至90℃搅拌反应12小时，反应结束后，加入50mL的水，分出有机相，水相用甲苯-THF萃取，收集有机相干燥，过滤，滤液减压浓缩干燥，用硅胶柱分离纯化，得到CJHB805，黄色固体，收率63％。EI-MS/FAB,m/e:571.72，计算值：571.23。
参照上述的合成方法，制备以下化合物：
Figure BDA0003315206340000293
Figure BDA0003315206340000301
实施例5
化合物CJHB780的制备方法，包括如下步骤：
第一步：化合物Int.-6的制备
Figure BDA0003315206340000302
取10.0mmol中间体A2与40mL的甲苯混合，在氮气保护下，加入12.0mmol的(4-(1-苯基-1H-苯并[d]咪唑-2-基)苯基)硼酸(CAS:952514-79-3)、48.0mmol的无水碳酸钾和15.0mg的Pd132催化剂，再加入20mL的乙醇和20mL的水，升温至回流搅拌反应12小时，冷却到室温，过滤，滤饼用水洗、乙醇洗，用硅胶柱分离纯化，得到化合物Int.-6，收率86％。
第二步：化合物Int.-7的制备
Figure BDA0003315206340000311
参照实施例1第五步的合成方法，仅将实施例1第五步的Int.-4替换为Int.-6，经过硅胶柱分离纯化，得到化合物Int.-7，收率92％。
第三步：化合物CJHB780的制备
Figure BDA0003315206340000312
取10.0mmol中间体Int.-7与60mL的THF混合，在氮气保护下，加入15.0mmol的苯硼酸、30.0mmol的无水碳酸钠和12.0mg的Pd(PPh3)4催化剂，再加入20mL的水，升温至回流搅拌反应12小时，冷却到室温，加入50mL的水稀释，用甲苯-THF萃取，收集有机相，干燥，过滤，滤液减压浓缩干燥，用硅胶柱分离纯化，得到化合物CJHB780，收率88％。EI-MS/FAB,m/e:672.96，计算值：672.26。
参照上述的合成方法，制备以下化合物：
Figure BDA0003315206340000313
Figure BDA0003315206340000321
实施例6
化合物CJHB783的制备方法，包括如下步骤：
第一步：化合物Int.-8的制备
Figure BDA0003315206340000322
取20.0mmol中间体A2与60mL的1,4-二氧六环混合，在氮气保护下，加入24.0mmol的联硼酸频那醇酯、30.0mmol的无水醋酸钾、0.2mmol的醋酸钯和0.4mmol的Xphos，升温至回流搅拌反应12小时，冷却到室温，加入50mL的水，用乙酸乙酯萃取，收集有机相，干燥，过滤，滤液减压浓缩干燥，用硅胶柱分离纯化，得到化合物Int.-8，收率87％。
第二步：化合物Int.-9的制备
Figure BDA0003315206340000331
参照实施例5第一步的合成方法，仅将实施例5第一步的A2替换为2-氯-4-苯基喹唑啉(CAS:29874-83-7)，将(4-(1-苯基-1H-苯并[d]咪唑-2-基)苯基)硼酸替换为Int.-8，经过硅胶柱分离纯化，得到化合物Int.-9，收率82％。
第三步：化合物Int.-10的制备
Figure BDA0003315206340000332
参照实施例1第五步的合成方法，仅将实施例1第五步的Int.-4替换为Int.-9，经过硅胶柱分离纯化，得到化合物Int.-10，收率94％。
第四步：化合物CJHB783的制备
Figure BDA0003315206340000333
参照实施例5第三步的合成方法，仅将实施例5第三步的Int.-7替换为Int.-10，经过硅胶柱分离纯化，得到化合物CJHB783，收率81％。EI-MS/FAB,m/e:608.85，计算值：608.23。
参照上述的合成方法，制备以下化合物：
Figure BDA0003315206340000334
Figure BDA0003315206340000341
实施例7
一种OLED元件，如图1所示，本实施例的OLED元件为底部发射光元件，包括基板1、设于基板1上的阳极层2、设于阳极层2上的空穴注入层3、设于空穴注入层3上的空穴传输层4、设于空穴传输层4上的有机发光层5、设于有机发光层5上的电子传输层6、设于电子传输层6上的电子注入层7、设于电子注入层7上的阴极层8，所述的OLED元件的制备方法包括如下步骤：
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，在上述阳极层膜上继续分别蒸镀化合物DNTPD作为空穴注入层，蒸镀膜厚为
Figure BDA0003315206340000342
在上述空穴注入层膜上继续蒸镀NPD为空穴传输层，蒸镀膜厚为
Figure BDA0003315206340000343
3)在空穴传输层上继续蒸镀一层化合物HT202作为电子阻挡层，蒸镀膜厚为
Figure BDA0003315206340000344
4)在电子阻挡层上继续蒸镀一层本发明的式I所示的蒽衍生物和BD017作为有机发光层，其中，BD017为掺杂材料和本发明的式(I)所示的蒽衍生物为主体材料，式(I)所示的化合物在BD017中的掺杂浓度为10％，蒸镀膜厚为
Figure BDA0003315206340000345
5)在上述有机发光层上再继续蒸镀一层化合物TPBI作为空穴阻挡层，蒸镀膜厚为
Figure BDA0003315206340000346
6)在上述空穴阻挡层上再继续蒸镀一层化合物LiQ和ET205作为器件的电子传输层，其中，LiQ和ET205的质量比为1:1，蒸镀膜厚为
Figure BDA0003315206340000347
7)在上述空穴阻挡层上再继续蒸镀一层化合物LiF作为器件的电子传输层，蒸镀膜厚为
Figure BDA0003315206340000351
最后，在上述电子传输层之上蒸镀金属铝作为元件的阴极层，蒸镀膜厚为
Figure BDA0003315206340000352
上述实施例7中使用的化合物结构如下：
Figure BDA0003315206340000353
实施例8
一种有机电致发光元件，为顶发射光元件，其结构如图2所示，包括基板1、设于基板1上的阳极层2、设于阳极层2上的空穴注入层3、设于空穴注入层3上的电子阻挡层4、设于电子阻挡层4上的有机发光层5、设于有机发光层5上的空穴阻挡层6、设于空穴阻挡层6上的电子注入层7、设于电子注入层7上的阴极层8。
具体的制备方法同实施例7所述的OLED元件。
对比例1
参照实施例7相同的步骤，不同之处在于使用化合物α,β-ADN代替式(I)所示的蒽衍生物。化合物α,β-ADN的结构为：
Figure BDA0003315206340000354
在电流密度为10mA/cm2条件下，测量了OLED元件的驱动电压、半峰宽FWHM、电流效率，以及在亮度为1000cd/m2初始条件下的器件寿命LT90％，并对以上数据相较于比较例1进行归一化，所得有机发光元件的性能检测结果示于下表1中：
表1
Figure BDA0003315206340000361
Figure BDA0003315206340000371
Figure BDA0003315206340000381
Figure BDA0003315206340000391
从表1中可以看出，本发明的化合物作为蓝光材料获得了深蓝光有机电致发光器件，相较于采用ɑ,β-ADN作为蓝光主体材料的有机电致发光元件，元件的电流效率更高、驱动电压相当，而且器件初始亮度在1000cd/m2的条件下，器件的LT90％寿命也有了很大的改善。
本发明的有机电致发光装置可以在壁挂电视、平板显示器、照明等的平面发光体、复印机、打印机、液晶显示器的背光源或计量仪器类等的光源，显示板、标识灯等中应用。
以上所述，仅为本发明的具体实施方式，但本发明的保护范围并不局限于此，任何熟悉本技术领域的技术人员在本发明揭露的技术范围内，可轻易想到变化或替换，都应涵盖在本发明的保护范围之内。因此，本发明的保护范围应以所述权利要求的保护范围为准。

Claims (8)

1.一种蒽衍生物，其特征在于，所述的蒽衍生物为以下CJHB751～CJHB879结构中的一种：
Figure FDA0003512141760000011
Figure FDA0003512141760000021
Figure FDA0003512141760000031
Figure FDA0003512141760000041
Figure FDA0003512141760000051
Figure FDA0003512141760000061
Figure FDA0003512141760000071
Figure FDA0003512141760000081
Figure FDA0003512141760000091
2.一种有机电致发光材料，其特征在于，所述的有机电致发光材料包括权利要求1所述的蒽衍生物。
3.一种有机电致发光装置，其特征在于，所述的有机电致发光装置包括第一电极、第二电极和置于所述的第一电极和所述的第二电极之间的至少一层有机层，所述有机层包含权利要求1所述的蒽衍生物。
4.根据权利要求3所述的有机电致发光装置，其特征在于，所述的有机层选自电子注入层、电子输送层、空穴阻挡层、电子阻挡层、空穴输送层、空穴注入层和发光层中的一种或几种。
5.根据权利要求4所述的有机电致发光装置，其特征在于，所述电子输送层、发光层包含所述的蒽衍生物。
6.根据权利要求5所述的有机电致发光装置，其特征在于，所述发光层包括掺杂物和发光主体，所述掺杂物包括由蒽、萘、蒽、芘、苝、菲、荧蒽、
Figure FDA0003512141760000092
苯并蒽、芴、螺芴和并五苯及其衍生物组成的群组；所述发光主体包含所述的蒽衍生物。
7.根据权利要求6所述的有机电致发光装置，其特征在于，所述的掺杂物与发光主体的质量比为1:99～50:50。
8.一种消费型产品，其特征在于，包含权利要求3-7任一项所述的有机电致发光装置。
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