CN114539075B - 一种芴衍生物及其应用 - Google Patents
一种芴衍生物及其应用 Download PDFInfo
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- CN114539075B CN114539075B CN202210135591.8A CN202210135591A CN114539075B CN 114539075 B CN114539075 B CN 114539075B CN 202210135591 A CN202210135591 A CN 202210135591A CN 114539075 B CN114539075 B CN 114539075B
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- organic electroluminescent
- fluorene derivative
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- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 title claims abstract description 26
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Abstract
本发明涉及有机电致发光材料技术领域,尤其涉及一种芴衍生物及其应用。所述芴衍生物的结构式如式(I)所示;本发明提供的式(I)所示的芴衍生物,增大了三芳胺的刚性,具有高的三线态能级,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,尤其涉及一种芴衍生物及其应用。
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己趋于成熟,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芴衍生物,该芴衍生物有效提高了材料热稳定性和输送载流子的能力,利用该芴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芴衍生物的应用。
具体地,本发明提供以下技术方案:
本发明提供一种芴衍生物,其结构式如式(I)所示:
其中,
Ar1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;
Z各自独立地选自CR10或N;
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10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;
式(II)的结构式如下:
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亚杂芳基;
*—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,Ar1选自由甲基、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;
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;
Z选自CR10;
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10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;
m选自0、1或2。
进一步地,R1、R2、R3、R4、R5、R6、R7、R8、R9、R10各自独立地为氢或式(II)所示基团。
作为优选,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;
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,所述芴衍生物的结构式选自由以下C473至C583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。
本发明还提供一种有机电致发光材料,其原料包括以上所述的芴衍生物;包括本发明的芴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层材料或电子阻挡层材料。
本发明同时提供以上所述的芴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层中的至少一层包括以上所述的芴衍生物。
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层或电子阻挡层。
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)所示的芴衍生物,增大了三芳胺的刚性,具有高的三线态能级,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。
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层。
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
式(I)所示化合物的合成路线如下:
其中,X1表示I、Br、Cl或OTf;在I-0至I-4中的R1~R9中其中之一为卤素或OTf,其它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:
第一步:中间体Int-1的制备
20.0mmol的1-溴-8-萘甲酸、50.0mmol的双(4-氯苯基)碘三氟甲磺酸盐、2.0mmol的醋酸钯和20.0mmol的叔丁醇钠以及100mL的二甲苯,通入氮气保护,升温至110℃搅拌反应24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,黄色固体,收率:64%。
第二步:中间体Int-2的制备
在氮气保护下,22.0mmol的苯硼酸、20.0mmol的Int-1、44.0mmol的无水碳酸钠和60mL的甲苯混合,再加入0.1mmol的Pd(PPh3)4催化剂和20mL乙醇以及20mL的水,升温至回流搅拌反应12小时,降至室温,加入100mL饱和盐水溶液,用乙酸乙酯萃取,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:87%。
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Int-3的制备
在氮气保护下,20.0mmol的中间体Int-2溶于80mL干燥的THF,降温至0℃,滴加入24.0mmol的苯基溴化镁THF溶液,升到室温搅拌反应2小时,滴加入20mL的1M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-3,白色固体,收率:90%。
第四步:化合物C-1的制备
在氮气保护下,20.0mmol的中间体Int-3溶于50mL干燥的二氯甲烷,降温至0℃,滴加入30.0mmol的三氟化硼乙醚,升到室温搅拌反应1小时,升温回流反应2小时,降到室温,滴加入50mL的10%氢氧化钠水溶液,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:92%。
参照上述类似的合成方法,制备以下表2所示化合物:
表2
参照上述类似的合成方法,仅将苯基溴化镁替换为甲基碘化镁,制备以下表3所示化合物:
表3
实施例2
化合物C500的制备方法,包括如下步骤:
第一步:中间体Int-5的制备
在氮气保护下,12.0mmol的9-([1,1'-联苯]-3-基)-3-溴-9H-咔唑溶于50mL干燥的THF,降温至-78℃,滴加入14.4mmol的2.5M正丁基锂正己烷溶液,搅拌反应1小时,再滴加入10.0mmol的Int-4溶于THF的溶液,升到室温搅拌反应1小时,滴加入20mL的1M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,黄色固体,收率:93%。
第二步:化合物C500的制备
参照实施例1第四步的合成方法,仅将实施例1第四步中的Int-3替换为Int-5,制备化合物C500,白色固体,收率:88%,真空升华后,HPLC:99.96%,MS(MALDI-TOF):m/z=608.2308[M+H]+;1HNMR(δ、CDCl3):8.81(1H,s);8.50(1H,s);8.25~8.18(4H,m);8.16~8.13(1H,m);7.92~7.90(1H,d);7.75~7.64(8H,m);7.61~7.48(6H,m);7.46~7.38(5H,m);7.21~7.18(1H,m);7.01~6.99(1H,d)。
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
化合物C580的制备方法,包括以下步骤:
第一步:化合物Int-6的制备
20.0mmol的C-4溶解于50mL的DMF中,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、0.1mmol的PdCl2(dppf)催化剂,2.0mmol的碘化亚铜,升温至100℃,搅拌反应12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,得到白色固体Int-6,收率82%。
第二步:化合物C580的制备
12.0mmol的Int-6溶解于40mL的甲苯中,在氮气保护下,加入10.0mmol的2-氯-4-苯基-6-联苯基-1,3,5-三嗪、36.0mmol的无水碳酸钠、0.01mmol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,得到白色固体C580,收率82%,真空升华后,HPLC:99.95%,MS(MALDI-TOF):m/z=674.2534[M+H]+;1HNMR(δ、CDCl3):9.06(1H,s);8.93(1H,s);8.50(1H,s);8.35~8.32(2H,m);8.17~8.14(1H,m);7.96~7.92(2H,m);7.74~7.68(5H,m);7.57~7.54(2H,m);7.52~7.47(4H,m);7.45~7.36(5H,m);7.26~7.17(5H,m);7.16~7.08(2H,m)。
参照上述类似的合成方法,制备以下表5所示化合物:
表5
实施例4
化合物C491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C491。
T3为CMe2,收率82%,真空升华后,HPLC:99.94%,MS(MALDI-TOF):m/z=726.3171[M+H]+;1HNMR(δ、CDCl3):8.32~8.26(2H,t);8.11~8.07(1H,d);7.94~7.90(2H,m);7.72~7.61(4H,m);7.55~7.42(8H,m);7.38~7.27(6H,m);7.22~7.17(3H,m);7.15~7.08(4H,m);7.02~6.96(3H,m);1.68(6H,s)。
T3为O,收率83%,真空升华后,HPLC:99.95%,MS(MALDI-TOF):m/z=700.2654[M+H]+;1HNMR(δ、CDCl3):8.32~8.29(1H,d);8.11~8.07(1H,d);7.97~7.94(1H,d);7.90~7.87(1H,m);7.72~7.62(7H,m);7.55~7.44(7H,m);7.39~7.32(5H,m);7.26~7.17(5H,m);7.15~7.08(4H,m);6.91~6.89(1H,d)。
参照上述类似的合成方法,制备以下表6所示化合物:
表6
实施例5
化合物C540的制备方法,包括如下步骤:
第一步:化合物Int-20的制备
参照实施例1第二步的合成方法,仅将Int-1替换为Int-0(实施例1的方法制备),将实施例1第二步中的苯硼酸替换为间甲氧基苯硼酸,制备化合物Int-20,黄色固体,收率93%。
第二步:化合物Int-21的制备
在氮气保护下,20.0mmol的Int-20溶于100mL的醋酸中,滴加入2mL的浓硫酸,升温至回流,搅拌反应2小时,降到室温,减压浓缩干,滴加入150mL的5%氢氧化钠水溶液,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-21,白色固体,收率:78%。
第三步:化合物Int-22的制备
在氮气保护下,20.0mmol的Int-21溶于80mL干燥的二氯甲烷中,降温至0℃,滴加入24.0mol的三溴化硼,搅拌反应1小时,升到室温,加入100mL饱和的碳酸钠水溶液,分出有机相,干燥,减压浓缩干,用硅胶柱分离纯化,得化合物Int-22,白色固体,收率:100%。
第四步:化合物Int-23的制备
在氮气保护下,15.0mmol的Int-22溶于50mL干燥的二氯甲烷中,加入22.5mmol的吡啶,降温至0℃,滴加入18.0mol的三氟甲磺酸酐,搅拌反应1小时,升到室温,加入50mL的2N稀盐酸,分出有机相,干燥,减压浓缩干,用硅胶柱分离纯化,得化合物Int-23,白色固体,收率:96%。
第五步:化合物Int-24的制备
参照实施例3第一步的合成方法,仅将实施例3第一步中的C-4替换为Int-23,制备化合物Int-24,白色固体,收率:86%。
第六步:化合物C540的制备
参照实施例3第二步的合成方法,仅将实施例3第二步中的Int-6替换为Int-24,将2-氯-4-苯基-6-联苯基-1,3,5-三嗪替换为2-氯-4,6-二苯基-1,3,5-三嗪制备化合物C540,白色固体,收率:84%,真空升华后,HPLC:99.89%,MS(MALDI-TOF):m/z=598.2291[M+H]+;1HNMR(δ、CDCl3):8.81~8.77(4H,m);8.45~8.42(1H,m);8.15~8.08(3H,m);7.92(1H,s);7.56~7.49(5H,m);7.46~7.37(8H,m);7.26~7.17(4H,m);7.02~6.97(1H,m)。
参照上述类似的合成方法,制备以下表7所示化合物:
表7
实施例6
化合物C525的制备:
12.0mmol的Int-23溶解于50mL的二甲苯中,在氮气保护下,加入10.0mmol的二([1,1'-联苯]-4-基)胺、18.0mmol的叔丁醇钠、0.1mmol的Pd2(dba)3催化剂,再加入0.2mmol的Xphos,升温至100℃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,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到化合物C525,收率84%,真空升华后,HPLC:99.97%,MS(MALDI-TOF):m/z=686.2788[M+H]+;1HNMR(δ、CDCl3):8.52~8.49(1H,m);8.24~8.21(2H,m);7.92~7.89(1H,m);7.74~7.66(6H,m);7.54~7.45(10H,m);7.42~7.35(7H,m);7.33~7.24(5H,m);7.16~7.12(2H,m);7.07~7.02(1H,m)。
参照上述类似的合成方法,制备以下表8所示化合物:
表8
实施例7
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。
实施例7中使用的化合物HI01、HTM、PHT、GD016、ET06和LiQ的结构如下:
实施例8
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7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7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7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9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9各元件性能检测结果
由表9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C555(T3为CMe2)发光效率有显著提高,而且在电流密度为50mA/cm2起始条件下的LT95%寿命有明显优势。
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 (6)
2.一种有机电致发光材料,其特征在于,其原料包括权利要求1所述的芴衍生物。
3.权利要求1所述的芴衍生物在制备有机电致发光元件中的应用。
4.一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层中的至少一层包括权利要求1所述的芴衍生物。
5.根据权利要求4所述的有机电致发光元件,其特征在于,所述有机层为空穴注入层、空穴传输层、空穴阻挡层、发光层、电子传输层、电子注入层、或电子阻挡层。
6.一种消费型产品,其特征在于,其包括权利要求4或5所述的有机电致发光元件。
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