CN115108921A - 一种苊衍生物及其应用 - Google Patents
一种苊衍生物及其应用 Download PDFInfo
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- CN115108921A CN115108921A CN202210832927.6A CN202210832927A CN115108921A CN 115108921 A CN115108921 A CN 115108921A CN 202210832927 A CN202210832927 A CN 202210832927A CN 115108921 A CN115108921 A CN 115108921A
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Classifications
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- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
本发明涉及有机电致发光材料技术领域，尤其涉及一种苊衍生物及其应用。所述苊衍生物的结构式如式(I)所示；本发明提供的式(I)所示的苊衍生物，增大了苊的共轭平面，提高了材料热稳定性和输送载流子的能力；将该芴衍生物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，尤其涉及一种苊衍生物及其应用。
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已趋于成熟，一些产品已进入市场，但在产业化过程中，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；尤其是发光元件的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。
鉴于此，特提出本发明。
发明内容
本发明的目的在于提供一种苊衍生物，该苊衍生物有效提高了材料热稳定性和输送载流子的能力，利用该苊衍生物制备的有机电致发光元件可显著降低驱动电压、提高发光效率和寿命；本发明的另一目的在于提供该苊衍生物的应用。
具体地，本发明提供以下技术方案：
本发明提供一种苊衍生物，其结构式如式(I)所示：
其中，Z为CR5R6—CR7R8、CR5＝CR6或CR5＝N；
R1、R2、R3、R4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C6-C60芳胺基、取代或未取代的C2-C60杂环芳基或式(II)组成的群组，并且在R1、R2、R3、R4中至少有一者为式(II)所示基团；
式(II)的结构式如下：
Ar1、Ar2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亚杂芳基；
R5、R6、R7、R8各自独立地选自由氢、氘、卤素、腈基、C1-C40烷基、C3-C40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、取代或未取代的C2-C60杂环芳基或式(II)组成的群组，或者相邻的两个或多个取代基任选地接合或稠合形成取代或未取代的环；
*—表示式(II)与式(I)的连接键。
本发明中，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。
作为优选，所述苊衍生物选自由以下所示结构组成的群组：
优选地，所述Ar1、Ar2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R1、R2、R3、R4、R5、R6、R7、R8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C6-C60芳胺基、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。
进一步地，所述R1、R2、R3、R4、R5、R6、R7、R8各自独立地为氢或式(II)所示基团。
作为优选，所述杂环芳基选自由以下II-1～II-17所示基团组成的群组：
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-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；
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或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；
作为优选，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、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的烷基、C2-C60的烯基、C2-C60的炔基、C1-C60的烷氧基、C3-C60的环烷烃基、C3-C60的环烯烃基、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或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；
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。
本发明中，“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的烷基、C2-C60的烯基、C2-C60的炔基、C1-C60的烷氧基、C3-C60的环烷基、C3-C60的环烯基、C6-C60的芳基、C6-C60的芳氧基、C6-C60的芳硫醚基和C2-C60的杂环芳基中的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。
作为优选，所述苊衍生物的结构式选自由以下C473至C601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。
本发明提供了式(I)所示化合物的合成路线，如下：
其中，X1、X2、X3表示I、Br、Cl或OTf；其它所用符号如上文中所定义。
本发明还提供一种有机电致发光材料，其原料包括以上所述的苊衍生物；包括本发明的苊衍生物的有机电致发光材料具有载流子传输的能力或光取出能力。
作为优选，所述有机电致发光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。
本发明同时提供以上所述的苊衍生物在制备有机电致发光元件中的应用。
本发明还提供一种有机电致发光元件，其包括：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、CPL中的至少一层包括以上所述的苊衍生物。
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。
作为优选，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或电子阻挡层。
本发明还提供一种消费型产品，其包括以上所述的有机电致发光元件。
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)所示的苊衍生物，增大了苊的共轭平面，提高了材料热稳定性和输送载流子的能力；将该苊衍生物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的示意图；
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。
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；
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。
具体实施方式
以下实施例用于说明本发明，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1
化合物C481的制备方法，包括如下步骤：
第一步：中间体Int-1的制备
20.0mmol的5-溴-6-碘-1,2-二氢苊、20.0mmol的对氯苯硼酸、0.1mmol的Pd(PPh3)4催化剂和30.0mmol的无水碳酸钠以及100mL的甲苯、20mL的乙醇，通入氮气保护，升温至回流搅拌反应12小时，降到室温，加入100mL的水，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，白色固体，收率：76％。
第二步：中间体Int-2的制备
在氮气保护下，20.0mmol的Int-1溶于60mL干燥的THF中，液氮降温至-78℃，滴加入22.0mmol的2.5M正丁基锂正己烷溶液，搅拌反应10分钟，再滴加入30.0mmol的无水丙酮，升至室温搅拌反应1小时，加入50mL饱和氯化铵水溶液，用乙酸乙酯萃取，有机相干燥，过滤，减压浓缩干，得到黄色油状物用50mL的二氯甲烷溶解，降温至0℃，滴加入40.0mmol的三氟化硼乙醚溶液，升温回流搅拌反应12小时，降到室温，加入50mL饱和盐水溶液，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，得到白色固体Int-2，收率：78％。
参照上述类似的合成方法，制备以下表1所示化合物：
表1
第三步：化合物C481的制备
在氮气保护下，22.0mmol的中间体Int-2溶于60mL干燥的甲苯中，加入20.0mmol的仲胺、30.0mmol的叔丁醇钠、2.0mmol的碘化亚铜、0.2mmol的Pd2(dba)3和0.4mmol的XantPhos，升温至110℃搅拌反应12小时，降到室温，加入50mL的水，分出有机相，水相用甲苯萃取，有机相干燥，减压浓缩干，用硅胶柱分离纯化，得化合物C481，白色固体；
T3为CMe2；收率：84％，MS(MALDI-TOF)：m/z＝554.2854[M+H]+；1HNMR(δ、CDCl3)：8.27～8.23(2H,d)；7.85～7.83(1H,d)；7.43(1H,s)；7.35～7.24(5H,m)；7.19～7.14(3H,m)；7.02～6.94(7H,m)；3.27(4H,s)；1.68(6H,s)；1.62(6H,s)。
T3为9,9-芴基(FR)；收率：82％，MS(MALDI-TOF)：m/z＝676.3012[M+H]+；1HNMR(δ、CDCl3)：8.23～8.21(1H,d)；7.90～7.84(3H,m)；7.54～7.47(2H,m)；7.45～7.36(4H,m)；7.33～7.22(9H,m)；7.20～7.12(5H,m)；7.08～7.05(2H,m)；7.03～6.97(1H,m)；3.27(4H,s)；1.74(6H,s)。
T3为O；收率：83％，MS(MALDI-TOF)：m/z＝528.2333[M+H]+；1HNMR(δ、CDCl3)：8.25～8.23(1H,d)；7.92～7.90(1H,d)；7.65～7.63(1H,d)；7.52～7.44(4H,m)；7.41～7.36(1H,m)；7.32～7.27(3H,m)；7.25～7.20(4H,m)；7.08～7.05(2H,m)；7.03～6.98(1H,m)；6.92～6.88(1H,m)；3.27(4H,s)；1.72(6H,s)。
T3为NPh；收率：85％，MS(MALDI-TOF)：m/z＝603.2814[M+H]+；1HNMR(δ、CDCl3)：8.25(1H,s)；8.17(1H,s)；7.93(1H,s)；7.73～7.71(1H,d)；7.62～7.56(3H,m)；7.51～7.47(5H,m)；7.36～7.34(1H,m)；7.30～7.25(5H,m)；7.22～7.16(3H,m)；7.08～7.05(2H,m)；7.02～6.98(1H,m)；3.27(4H,s)；1.73(6H,s)。
参照上述类似的合成方法，制备以下表2所示化合物：
表2
实施例2
化合物C588的制备方法，包括如下步骤：
第一步：中间体Int-14的制备
在氮气保护下，20.0mmol的6-溴苊-2-酮溶于50mL的三氯氧磷，升温回流搅拌反应12小时，减压浓缩干，用硅胶柱分离纯化，得化合物Int-14，黄色固体，收率：93％。
第二步：中间体Int-15的制备
在氮气保护下，20.0mmol的Int-14、22.0mmol的苯硼酸、40.0mmol的无水碳酸钠、0.2mmol的Pd(PPh3)4催化剂溶于50mL的甲苯、25mL的乙醇和25mL的水中，升温至回流搅拌反应12小时，降到室温，加入20mL的水稀释，用乙酸乙酯萃取，收集有机相，干燥，减压浓缩干，硅胶柱分离纯化，得化合物Int-15，黄色固体，收率：85％。
第三步：中间体Int-16的制备
在氮气保护下，20.0mmol的Int-15溶于50mL的DMF，降温至0℃，分批加入22.0mmol的NBS，搅拌反应1小时，升至室温搅拌反应12小时，将反应液倒入150mL的水中，用乙酸乙酯萃取，收集有机相，用饱和盐水洗，干燥，减压浓缩干，硅胶醉分离纯化，得化合物Int-16，黄色固体，收率：87％。
第四步：中间体Int-17的制备
参照实施例1第二步的合成方法，仅将实施例1第二步的Int-1替换为Int-16，制备化合物Int-17，收率83％。
参照上述类似的合成方法，制备以下表3所示化合物：
表3
第五步：化合物C588的制备
参照实施例1第三步的合成方法，仅将实施例1第三步中的Int-2替换为Int-17，制备化合物C588，黄色固体，收率：82％，真空升华为白色固体，MS(MALDI-TOF)：m/z＝608.2308[M+H]+；1HNMR(δ、CDCl3)：8.55(1H,s)；8.18(1H,s)；8.12～8.10(2H,d)；7.76～7.74(2H,m)；7.58～7.49(5H,m)；7.42～7.34(6H,m)；7.31～7.26(4H,m)；7.24～7.17(3H,m)；7.15～7.07(5H,m)；7.04(1H,s)；1.62(6H,s)。
参照上述类似的合成方法，制备以下表4所示化合物：
表4
实施例3
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CPL110，其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ITO膜上蒸镀金属银作为阳极层，蒸镀膜厚为
蒸镀化合物HI01和HI102作为空穴注入层，其中HI102为HI01质量的3％，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GD010为掺杂材料，GD010为PHT质量的3％，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1:10，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，蒸镀膜厚为
得到本发明提供的OLED元件。
实施例3中使用的化合物HI01、HI102、HTM、PHT、GD010、ET06和LiQ的结构如下：
实施例4
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CPL111。
对比例1
按照与实施例3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；B-1结构式如下：
对比例2
按照与实施例3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；B-2结构式如下：
对比例3
按照与实施例3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；B-3结构式如下：
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5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5各元件性能检测结果
其中，FR为9,9-芴基；Ph为苯基；PhPh为联苯基；Me为甲基。
由表5可知，本发明的苊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C517发光效率和LT95％寿命性能提高明显，苊衍生物的LT95％寿命表现优秀，说明化合物的稳定性得到提高，是性能优异的电子阻挡层材料。
本发明的苊衍生物与对比例1的化合物B-1相比，区别在于苊的稳定性提高，电子传输性能减弱，元件内部的激子复合被限制在发光层中，因此，本发明的化合物在发光元件的性能表现上更加优异。
本发明的苊衍生物与对比例2的化合物B-2相比，区别在于B-2的苊片段是螺芴基，螺芴基的结构是正交结构，空间位阻很大，不利于分子的紧密堆砌，而本发明的苊衍生物为甲基，平面位阻小，其在分子成膜及电荷的传输性能上均较优异，元件内电荷的传输更加平衡，因此，本发明的化合物在发光元件的性能表现上更加优异。
本发明的苊衍生物与对比例3的化合物B-3相比，区别在于B-3的苊片段是苯基，虽然苯基的位阻小，对分子成膜的影响较小，但甲基与苯基相比，平面位阻小，共轭能力较弱，使元件内电荷的传输更加平衡，因此，元件性能提高。
虽然，上文中已经用一般性说明及具体实施方案对本发明作了详尽的描述，但在本发明基础上，可以对之作一些修改或改进，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 (10)
1.一种苊衍生物，其特征在于，其结构式如式(I)所示：
其中，Z为CR5R6—CR7R8、CR5＝CR6或CR5＝N；
R1、R2、R3、R4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C6-C60芳胺基、取代或未取代的C2-C60杂环芳基或式(II)组成的群组，并且在R1、R2、R3、R4中至少有一者为式(II)所示基团；
式(II)的结构式如下：
Ar1、Ar2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亚杂芳基；
R5、R6、R7、R8各自独立地选自由氢、氘、卤素、腈基、C1-C40烷基、C3-C40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、取代或未取代的C2-C60杂环芳基或式(II)组成的群组，或者相邻的两个或多个取代基任选地接合或稠合形成取代或未取代的环；
*—表示式(II)与式(I)的连接键。
2.根据权利要求1所述的苊衍生物，其特征在于，所述苊衍生物选自由以下所示结构组成的群组：
Ar1、Ar2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；
R1、R2、R3、R4、R5、R6、R7、R8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C6-C60芳胺基、取代或未取代的C2-C60杂环芳基组成的群组；
m选自0、1或2。
3.根据权利要求1或2所述的苊衍生物，其特征在于，所述C2-C60杂环芳基选自由以下II-1～II-17所示基团组成的群组：
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-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；
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或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；
4.根据权利要求1-3任一项所述的苊衍生物，其特征在于，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、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的烷基、C2-C60的烯基、C2-C60的炔基、C1-C60的烷氧基、C3-C60的环烷烃基、C3-C60的环烯烃基、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或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；
5.根据权利要求1-4任一项所述的苊衍生物，其特征在于，所述苊衍生物的结构式选自由以下C473至C601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。
6.一种有机电致发光材料，其特征在于，其原料包括权利要求1-5任一项所述的苊衍生物。
7.权利要求1-5任一项所述的苊衍生物在制备有机电致发光元件中的应用。
8.一种有机电致发光元件，其特征在于，其包括：第一电极、第二电极、CPL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、CPL中的至少一层包括权利要求1-5任一项所述的苊衍生物。
9.根据权利要求8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或电子阻挡层。
10.一种消费型产品，其特征在于，其包括权利要求8或9所述的有机电致发光元件。
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09216855A (ja) * | 1996-02-09 | 1997-08-19 | Hodogaya Chem Co Ltd | アセナフテン化合物 |
| US20070252141A1 (en) * | 2006-04-25 | 2007-11-01 | Canon Kabushiki Kaisha | Organic compound and organic light-emitting element |
| CN104768926A (zh) * | 2012-10-12 | 2015-07-08 | 东丽株式会社 | 1,2-苯并苊衍生物、含有其的发光元件材料及发光元件 |
| CN107522653A (zh) * | 2017-09-01 | 2017-12-29 | 上海道亦化工科技有限公司 | 一种苊类有机电致发光化合物及其有机电致发光器件 |
| CN107586273A (zh) * | 2017-09-01 | 2018-01-16 | 上海道亦化工科技有限公司 | 一种苊类有机电致发光化合物及其有机电致发光器件 |
| CN111362950A (zh) * | 2020-04-15 | 2020-07-03 | 苏州久显新材料有限公司 | 苊并氮杂萘类衍生物及其制备方法和电子器件及发光光谱调节方法 |
| CN114702432A (zh) * | 2022-04-01 | 2022-07-05 | 上海钥熠电子科技有限公司 | 一种含苊的化合物及其在有机电致发光器件中的应用 |
-
2022
- 2022-07-14 CN CN202210832927.6A patent/CN115108921A/zh active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09216855A (ja) * | 1996-02-09 | 1997-08-19 | Hodogaya Chem Co Ltd | アセナフテン化合物 |
| US20070252141A1 (en) * | 2006-04-25 | 2007-11-01 | Canon Kabushiki Kaisha | Organic compound and organic light-emitting element |
| CN104768926A (zh) * | 2012-10-12 | 2015-07-08 | 东丽株式会社 | 1,2-苯并苊衍生物、含有其的发光元件材料及发光元件 |
| CN107522653A (zh) * | 2017-09-01 | 2017-12-29 | 上海道亦化工科技有限公司 | 一种苊类有机电致发光化合物及其有机电致发光器件 |
| CN107586273A (zh) * | 2017-09-01 | 2018-01-16 | 上海道亦化工科技有限公司 | 一种苊类有机电致发光化合物及其有机电致发光器件 |
| CN111362950A (zh) * | 2020-04-15 | 2020-07-03 | 苏州久显新材料有限公司 | 苊并氮杂萘类衍生物及其制备方法和电子器件及发光光谱调节方法 |
| CN114702432A (zh) * | 2022-04-01 | 2022-07-05 | 上海钥熠电子科技有限公司 | 一种含苊的化合物及其在有机电致发光器件中的应用 |
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