CN114605411A - 一种吖啶衍生物及其应用 - Google Patents
一种吖啶衍生物及其应用 Download PDFInfo
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- CN114605411A CN114605411A CN202210334922.0A CN202210334922A CN114605411A CN 114605411 A CN114605411 A CN 114605411A CN 202210334922 A CN202210334922 A CN 202210334922A CN 114605411 A CN114605411 A CN 114605411A
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- QQTOBDXDQYCGMA-UHFFFAOYSA-N naphtho[2,3-e][1,3]benzoxazole Chemical class C1=CC=C2C=C3C(N=CO4)=C4C=CC3=CC2=C1 QQTOBDXDQYCGMA-UHFFFAOYSA-N 0.000 description 1
- 150000005054 naphthyridines Chemical class 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- VXNSQGRKHCZUSU-UHFFFAOYSA-N octylbenzene Chemical compound [CH2]CCCCCCCC1=CC=CC=C1 VXNSQGRKHCZUSU-UHFFFAOYSA-N 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 150000002988 phenazines Chemical class 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- GDISDVBCNPLSDU-UHFFFAOYSA-N pyrido[2,3-g]quinoline Chemical class C1=CC=NC2=CC3=CC=CN=C3C=C21 GDISDVBCNPLSDU-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 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
- 150000003577 thiophenes Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 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
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
Description
技术领域
本发明涉及有机电致发光材料技术领域,尤其涉及一种吖啶衍生物及其应用。
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吖啶衍生物,该吖啶衍生物有效提高了材料热稳定性和输送载流子的能力,利用该吖啶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吖啶衍生物的应用。
具体地,本发明提供以下技术方案:
本发明提供一种吖啶衍生物,其结构式如式(I)所示:
其中,
G选自O、S、CR’R”或NAr2;
R’、R”、Ar1、Ar2各自独立地选自由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、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、取代或未取代的C2-C60杂环芳基组成的群组;R1至R12和Ar1中至少有一者是式(II)所示的基团,R1至R12中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:
Ar3、Ar4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,Ar3和Ar4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;
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。
进一步地,所述R’、R”、Ar1、Ar2各自独立地选自由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、或者取代或未取代的C2-C60杂环芳基组成的群组。
进一步地,所述R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12各自独立地选自由氢、氘、卤素、腈基、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C2-C60杂环芳基组成的群组;R1、R2、R3、R4、R6、R7、R8、R9、R10、R11、R12中至少有一者是式(II)所示的基团。
进一步地,所述Ar3、Ar4各自独立地选自由取代或未取代的C6-C60芳基或者取代或未取代的C2-C60杂环芳基组成的群组。
进一步地,所述m选自0、1或2。
根据本发明的一个实施例,所述R’、R”、R5各自独立地选自甲基、乙基、环戊基、环己基、取代或未取代的C6-C60芳基、或者取代或未取代的C2-C60杂环芳基组成的群组;优选地,R’、R”、R5各自独立地选自甲基、苯基或芴基。
根据本发明的一个实施例,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芳胺基组成的群组;优选地,Ar1、Ar2各自独立地选自苯基、联苯基、萘基、芴基、菲基、三亚苯基。
根据本发明的一个实施例,所述Ar3、Ar4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。
根据本发明的一个实施例,所述R1、R2、R3、R4、R6、R7、R8、R9、R10、R11、R12各自独立地选自由氢、氟、腈基、甲基、乙基、叔丁基、取代或未取代的C6-C60芳基、取代或未取代的C2-C60杂环芳基组成的群组;优选地,R1、R2、R3、R4、R6、R7、R8、R9、R10、R11、R12各自独立地选自氢、甲基或叔丁基;R1、R2、R3、R4、R6、R7、R8、R9、R10、R11、R12中至少有一者为式(II)所示的基团。
作为优选,根据本发明的一个实施例,所述R’、R”、R5各自独立地为甲基或苯基。
作为优选,根据本发明的一个实施例,所述Ar1、Ar2各自独立地选自苯基、联苯基、萘基。
作为优选,根据本发明的一个实施例,所述R1、R2、R3、R4、R6、R7、R8、R9、R10、R11、R12各自为氢或式(II)所示的基团,并且至少有一个为式(II)所示的基团。
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、CRxRy或NAr5;
Rx、Ry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,Rx和Ry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,Rx、Ry为甲基、苯基或芴基;
Ar5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,Ar5为甲基、乙基、苯基或萘基;
本发明的芳基或稠环芳基,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,所述吖啶衍生物的结构式选自由以下D415至D558组成的群组:
其中,*—T3—*选自*—O—*、*—S—*或下述结构中的一种:
*—G—*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吖啶衍生物;包括本发明的吖啶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吖啶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吖啶衍生物。
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。
一般来说,OLED包含至少一个有机层,其安置在阳极与阴极之间且与阳极和阴极电连接。图1展示有机发光装置100示意图。图示不一定按比例绘制。装置100可包含衬底101、阳极102、空穴注入层103、空穴传输层104、电子阻挡层105、发光层106、电子传输层107、电子注入层108、阴极109以及封盖层(CPL)110。装置100可通过依序沉积所描述的层来制造。
图2展示倒转的有机发光装置200示意图。所述装置包含衬底201、阴极202、发光层203、空穴传输层204以及阳极205。可通过依序沉积所描述的层来制备装置200。因为最常见的OLED装置具有安置在阳极上的阴极,而装置200具有安置在阳极205下的阴极202,因此装置200可称为“倒转”有机发光装置。在装置200的对应层中,可使用与关于装置100所描述的材料类似的材料。图2提供可如何从装置100的结构省略一些层的一个实例。
图1和图2中所说明的简单分层结构是作为非限制实例而提供,且应当理解,可结合各种各样的其它结构使用本发明的实施例。所描述的特定材料和结构本质上是示范性的,且可使用其它材料和结构。可基于设计、性能和成本因素,通过以不同方式组合所描述的各个层来实现功能性OLED,或可完全省略若干层。还可包含未具体描述的其它层。可使用不同于具体描述的材料。尽管本文所提供的实例中的许多实例将各种层描述为包括单一材料,但将理解,可使用材料的组合,例如基质与掺杂剂的混合物,或更一般来说,混合物。并且,所述层可具有各种子层。本文中给予各个层的名称不意欲为严格限制性的。举例来说,在装置200中,空穴传输层204传输空穴并将空穴注入到发光层203中,且可被描述为空穴传输层或空穴注入层。在一个实施例中,可将OLED描述为具有安置在阴极与阳极之间的有机层。此有机层可包括单个层或可进一步包括如例图1和图2所描述的不同有机材料的多个层。
还可使用未具体描述的结构和材料,例如包含聚合物材料的PLED。作为另一实例,可使用具有单个有机层的OLED或多个堆叠。OLED结构可脱离图1和图2中所说明的简单分层结构。举例来说,衬底可包含有角度的反射表面以改进光耦合。
另一方面,关于本发明的有机电致发光元件,除了上述有机物层中的一层以上包含以上所述的吖啶衍生物之外,可以利用本领域中公知的材料和方法来形成有机物层和电极制造。
此外,可用作根据本发明的有机电致发光元件中所包含的阳极的物质没有特别限定,作为非限制性例子,可以使用钒、铬、铜、锌、金、铝等金属或它们的合金;氧化锌、氧化铟、氧化铟锡(ITO)、氧化铟锌(IZO)等金属氧化物;ZnO:Al或SnO2:Sb等金属与氧化物的组合;聚噻吩、聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧)噻吩](PEDT)、聚吡咯和聚苯胺等导电性高分子;以及炭黑等。
可用作根据本发明的有机电致发光元件中所包含的阴极的物质没有特别限定,作为非限制性例子,可以使用镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡或铅等金属或它们的合金;及LiF/Al或Li2O/Al等多层结构物质等。
可用作根据本发明的有机电致发光元件中所包含的基板的物质没有特别限定,作为非限制性例子,可以使用硅片、石英、玻璃板、金属板或塑料膜和片等。
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。
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)所示的吖啶衍生物,增大了三芳胺的刚性,具有高的三线态能级,高的材料热稳定性和输送载流子的能力;将该茚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为本发明的有机发光装置100示意图;
图1中,101是衬底、102是阳极、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、111是封盖层(CPL)。
图2为本发明倒转的有机发光装置200示意图;
图2中,201是衬底、202是阴极、203是发光层、204是空穴传输层、205是阳极。
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,X表示H、I、Br、Cl或OTf;R表示H、烷基、芳基等取代基,其它所用符号如上文中所定义。
实施例1
化合物D415的制备方法,以G为NPh为例,包括如下步骤:
第一步:中间体Int-1的制备
在氮气保护下,30.0mmol的镁屑和50mL干燥的THF,加入一粒碘,加热至沸,滴加入20.0mmol的5-氯-3-溴-1-苯基吲哚溶于20mL干燥的THF溶液,回流反应1小时,降温至0℃,滴加入22.0mmol的邻胺基苯腈溶于THF的溶液,搅拌反应30分钟,升到室温,滴加入20mL的饱和氯化铵水溶液,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:82%。
第二步:中间体Int-2的制备
在氮气保护下,13.0mmol的甲基三苯基磷溴盐分散在100mL干燥的THF中,加入26.0mmol的叔丁醇钠,搅拌反应30分钟,再加入10.0mmol的Int-1,升温至65℃搅拌反应15小时,加入50mL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:75%。
第三步:中间体Int-3的制备
在氮气保护下,20.0mmol的Int-2、24.0mmol的邻溴碘苯、0.2mmol的Pd2(dba)3、0.4mmol的Xantphos、40.0mmol的叔丁醇钠和60mL的甲苯混合,升温至100℃搅拌反应12小时,降到室温,加入20mL饱和盐水溶液,用甲苯萃取,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-3,收率:86%。
第四步:化合物Int-4的制备
在氮气保护下,20.0mmol的Int-3、1.0mmol的醋酸钯、40.0mmol的特戊酸、40.0mmol的无水碳酸钾、4.0mmol的DPPF和80mL的DMA混合,升温至120℃搅拌反应12小时,降到室温,减压浓缩干,用硅胶柱分离纯化,得到黄色固体Int-4,收率:86%。
第五步:化合物Int-5的制备
在氮气保护下,10.0mmol的Int-4溶解于40mL的甲苯中,加入12.0mmol的溴苯、15.0mmol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Int-5,收率:87%。
第六步:化合物D415(G为NPh)的制备
12.0mmol的Int-5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,过滤,滤饼用水洗、乙醇洗,用THF溶解,过硅胶短柱,洗脱液减压浓缩干,得到化合物D415,收率:84%,真空升华后,HPLC:99.96%,MS(MALDI-TOF):m/z=704.3081[M+H]+;1HNMR(δ、CDCl3):8.01(1H,s);7.92~7.90(1H,d);7.74~7.71(2H,m);7.62~7.53(5H,m);7.51~7.40(6H,m);7.29~7.21(6H,m);7.19~7.07(9H,m);7.02~6.94(3H,m);6.43~6.41(1H,d);2.37(3H,s)。
参照上述类似的合成方法,制备以下化合物:
将实施例第一步的5-氯-3-溴-1-苯基吲哚替换为5-氯-3-溴苯并呋喃制备G为O的化合物D415,收率:88%,真空升华后,HPLC:99.94%,MS(MALDI-TOF):m/z=629.2607[M+H]+;1HNMR(δ、CDCl3):8.21(1H,s);7.74~7.71(2H,m);7.58~7.53(3H,m);7.50~7.36(7H,m);7.28~7.13(9H,m);7.11~7.05(4H,m);7.02~6.94(3H,m);2.26(3H,s)。
将实施例第一步的5-氯-3-溴-1-苯基吲哚替换为5-氯-3-溴苯并噻吩制备G为S的化合物D415,收率:82%,真空升华后,HPLC:99.95%,MS(MALDI-TOF):m/z=645.2382[M+H]+;1HNMR(δ、CDCl3):7.92(1H,s);7.86~7.84(1H,d);7.76~7.72(2H,m);7.57~7.44(5H,m);7.42~7.35(5H,m);7.28~7.14(8H,m);7.10~7.04(4H,m);7.02~6.94(3H,m);2.27(3H,s)。
替换上述实施例第六步的二芳基胺制备化合物D416~D430。
使用不同的卤代物替换上述实施例中第五步的溴苯以及第六步的二芳基胺,制备化合物D493~D529、D545、D546、D551~D558。
实施例2
化合物D444的制备方法,以G为C(CH3)2为例,包括如下步骤:
第一步:中间体Int-6的制备
参照实施例1的合成方法,将实施例1第一步的5-氯-3-溴-1-苯基吲哚替换为3-溴-1,1-甲基-1H-茚,制备化合物Int-6,黄色固体,收率:88%。
第二步:中间体Int-7的制备
参照实施例1的合成方法,仅将实施例1第二步的Int-1替换为Int-6,制备化合物Int-7,黄色固体,收率:76%。
第三步:中间体Int-8的制备
参照实施例1的合成方法,仅将实施例1第三步的Int-2替换为Int-7,制备化合物Int-8,黄色固体,收率:85%。
第四步:化合物Int-9的制备
参照实施例1的合成方法,仅将实施例1第四步的Int-3替换为Int-8,制备化合物Int-8,黄色固体,收率:79%。
第五步:化合物D444(G为C(CH3)2)的制备
在氮气保护下,10.0mmol的Int-9溶解于50mL的甲苯中,加入12.0mmol的N,N-二([1,1'-联苯基]-4-基)-4'-氯-[1,1'-联苯基]-4-胺、15.0mmol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Xphos,升温至110℃搅拌反应16小时,降到室温,加入20mL的水稀释,过滤,滤饼用水洗、乙醇洗,用THF溶解,过硅胶短柱,洗脱液减压浓缩干,得到化合物D444,收率:87%,真空升华后,HPLC:99.93%,MS(MALDI-TOF):m/z=807.3747[M+H]+;1HNMR(δ、CDCl3):7.90(1H,s);7.76~7.72(4H,m);7.57~7.52(8H,m);7.50~7.42(10H,m);7.40~7.21(12H,m);7.09~7.04(1H,m);6.98~6.94(1H,m);1.62(3H,s);1.43(6H,s)。
参照上述类似的合成方法,制备以下化合物:
将实施例2第一步的3-溴-1,1-甲基-1H-茚替换为3-溴-1-芳基吲哚制备G为氮芳基的化合物D444,G为NPh时收率:83%,真空升华后,HPLC:99.95%,MS(MALDI-TOF):m/z=856.3705[M+H]+;1HNMR(δ、CDCl3):8.26(1H,s);7.96~7.93(1H,m);7.76~7.71(4H,m);7.65~7.62(2H,m);7.58~7.52(9H,m);7.50~7.39(9H,m);7.37~7.33(9H,m);7.30~7.26(2H,m);7.21~7.14(3H,m);6.97~6.94(1H,m);6.69~6.67(1H,m);2.38(3H,s)。
将实施例2第一步的3-溴-1,1-甲基-1H-茚替换为3-溴苯并噻吩制备G为S的化合物D444,收率:80%,真空升华后,HPLC:99.92%,MS(MALDI-TOF):m/z=797.3006[M+H]+;1HNMR(δ、CDCl3):7.95~7.93(1H,m);7.76~7.71(5H,m);7.58~7.47(13H,m);7.45~7.36(13H,m);7.29~7.26(1H,m);7.21~7.14(3H,m);6.97~6.94(1H,m);2.39(3H,s)。
将实施例2第一步的3-溴-1,1-甲基-1H-茚替换为3-溴苯并呋喃制备G为O的化合物D444,收率:86%,真空升华后,HPLC:99.96%,MS(MALDI-TOF):m/z=781.3233[M+H]+;1HNMR(δ、CDCl3):7.85(1H,s);7.77~7.72(4H,m);7.57~7.44(14H,m);7.42~7.35(12H,m);7.32~7.25(2H,m);7.20~7.13(3H,m);6.97~6.94(1H,m);2.38(3H,s)。
使用不同的卤代物替换上述实施例中第五步的N,N-二([1,1'-联苯基]-4-基)-4'-氯-[1,1'-联苯基]-4-胺制备化合物D431~D443、D445~D449、D547~D550。
实施例3
化合物D463(以G为NPh为例)的制备:
在氮气保护下,12.0mmol的Int-10(参照实施例1的合成方法制备)溶解于60mL的甲苯中,加入10.0mmol的二芳基胺、15.0mmol的叔丁醇钠、0.1mmol的Pd2(dba)3催化剂,再加入0.2mmol的Xphos,升温至110℃搅拌反应12小时,降到室温,加入20mL的水稀释,过滤,滤饼用水洗、乙醇洗,用THF溶解,过硅胶短柱,洗脱液减压浓缩干,得到化合物D463,收率:87%,真空升华后,HPLC:99.96%,MS(MALDI-TOF):m/z=856.3711[M+H]+;1HNMR(δ、CDCl3):8.24(1H,s);7.95~7.93(1H,m);7.62~7.59(6H,m);7.57~7.52(9H,m);7.50~7.45(6H,m);7.42~7.32(13H,m);7.26~7.21(3H,m);7.14~7.12(1H,d);7.02~7.00(1H,d);6.70~6.67(1H,m);2.31(3H,s)。
G为C(CH3)2,收率:78%,真空升华后,HPLC:99.89%,MS(MALDI-TOF):m/z=807.3749[M+H]+;1HNMR(δ、CDCl3):7.76~7.72(6H,m);7.57~7.46(14H,m);7.44~7.35(11H,m);7.24~7.21(1H,m);7.17~7.11(4H,m);7.05~7.02(1H,m);1.62(3H,s);1.43(6H,s)。
G为O,收率:85%,真空升华后,HPLC:99.92%,MS(MALDI-TOF):m/z=781.3225[M+H]+;1HNMR(δ、CDCl3):7.86~7.83(1H,m);7.62~7.59(7H,m);7.57~7.50(6H,m);7.48~7.39(12H,m);7.37~7.25(8H,m);7.21(1H,s);7.14~7.12(1H,d);7.06~7.04(1H,d);2.27(3H,s)。
G为S,收率:83%,真空升华后,HPLC:99.95%,MS(MALDI-TOF):m/z=797.2996[M+H]+;1HNMR(δ、CDCl3):7.95~7.92(1H,m);7.76~7.72(7H,m);7.57~7.48(13H,m);7.46~7.40(6H,m);7.38~7.32(6H,m);7.28~7.22(2H,m);7.14~7.12(1H,d);7.05~7.03(1H,d);2.27(3H,s)。
参照上述类似的合成方法,制备化合物:D450~D462、D464~D471、D482、D487~D492。
实施例4
化合物D479(以G为NPh为例)的制备:
在氮气保护下,10.0mmol的Int-10(参照实施例1的合成方法制备)溶解于40mL的甲苯中,加入12.0mmol的(4-(9H-咔唑-9-基)苯基)硼酸、25.0mmol的无水碳酸钠、0.1mmol的Pd(PPh3)4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,降到室温,加入40mL的水稀释,过滤,滤饼用水洗、乙醇洗,用THF溶解,过硅胶短柱,洗脱液减压浓缩干,得到化合物D479,收率:87%,真空升华后,HPLC:99.95%,MS(MALDI-TOF):m/z=869.3662[M+H]+;1HNMR(δ、CDCl3):8.54~8.52(2H,m);8.26~8.24(1H,m);7.95~7.90(6H,m);7.74(1H,s);7.64~7.56(4H,m);7.52~7.44(5H,m);7.38~7.22(9H,m);7.20~7.12(6H,m);7.09~7.04(4H,m);7.01~6.97(2H,m);6.64~6.59(1H,m);2.35(3H,s)。
G为C(CH3)2,收率:84%,真空升华后,HPLC:99.92%,MS(MALDI-TOF):m/z=820.3711[M+H]+;1HNMR(δ、CDCl3):8.55~8.52(2H,m);8.01(1H,s);7.95~7.90(5H,m);7.58~7.54(2H,m);7.52~7.34(6H,m);7.24~7.10(13H,m);7.08~6.97(7H,m);1.43(6H,s);1.08(3H,s)。
G为O,收率:86%,真空升华后,HPLC:99.95%,MS(MALDI-TOF):m/z=794.3187[M+H]+;1HNMR(δ、CDCl3):8.55~8.52(2H,m);8.22(1H,s);7.95~7.90(5H,m);7.74(1H,s);7.62~7.58(2H,m);7.52~7.40(5H,m);7.38~7.30(3H,m);7.28~7.12(11H,m);7.09~6.98(6H,m);2.26(3H,s)。
G为S,收率:86%,真空升华后,HPLC:99.97%,MS(MALDI-TOF):m/z=810.2957[M+H]+;1HNMR(δ、CDCl3):8.55~8.52(2H,m);8.21(1H,s);7.95~7.90(5H,m);7.75~7.72(2H,m);7.49~7.41(6H,m);7.38~7.34(3H,m);7.29~7.12(11H,m);7.09~6.98(6H,m);2.26(3H,s)。
参照上述类似的合成方法,制备化合物:D472~D478、D480、D481、D483~D486、D530~D544。
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、电子传输层108、电子注入层109、阴极层110,以及设于阴极层110之上的CPL层111,其制备方法(不包括空穴阻挡层)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5中使用的化合物HTP、HTM、BH11、BD16、ET08和LiQ的结构如下:
对比例1
按照与实施例5相同的步骤,将步骤2)中的式(I)所示的化合物替换为HI01,得到对比元件1;HI01结构式如下:
对比例2
按照与实施例5相同的步骤,将步骤2)中的式(I)所示的化合物替换为HI02,得到对比元件2;HI02结构式如下:
对上述过程制备的有机电致发光元件进行如下性能测试:
在同样亮度下,使用数字源表及亮度计测定实施例5及对比例1和对比例2中制备得到的有机电致发光元件的驱动电压和电流效率以及元件的寿命。具体而言,以每秒0.1V的速率提升电压,测定当有机电致发光元件的电流密度达到10mA/cm2时的电压即驱动电压,同时测出此时的亮度;亮度与电流密度的比值即为电流效率;LT95%寿命测试如下:使用亮度计在1000cd/m2亮度下,保持恒定的电流,测量有机电致发光元件的亮度衰减为950cd/m2的时间,单位为小时。
表1各元件性能检测结果
由表1可知,本发明的吖啶衍生物作为空穴注入层材料制备成的发光元件同样在10mA/cm2条件下,效率有提高显著,而且LT95%寿命有明显优势,是性能良好的空穴注入材料。
对比例2中的化合物HI02与本发明式(I)所示的化合物相比,区别在于吖啶母核的共轭平面小,共轭能力较弱,而苯并呋喃、苯并噻吩或吲哚为平面的吖啶母核,共轭平面增强、增大,所以其在分子成膜及电荷的传输上均较HI02优异,使元件内电荷的传输更加平衡,在元件性能和寿命上表现更有优势。
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 (10)
1.一种吖啶衍生物,其特征在于,其结构式如式(I)所示:
其中,
G选自O、S、CR’R”或NAr2;
R’、R”、Ar1、Ar2各自独立地选自由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、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、取代或未取代的C2-C60杂环芳基组成的群组;R1至R12和Ar1中至少有一者是式(II)所示的基团,R1至R12中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:
Ar3、Ar4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,Ar3和Ar4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;
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。
2.根据权利要求1所述的吖啶衍生物,其特征在于,所述R’、R”、Ar1、Ar2各自独立地选自由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、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、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C2-C60杂环芳基组成的群组;R1、R2、R3、R4、R6、R7、R8、R9、R10、R11、R12中至少有一者是式(II)所示的基团;
式(II)的结构式如下:
Ar3、Ar4各自独立地选自由取代或未取代的C6-C60芳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、1或2;
*—表示式(II)与式(I)的连接键。
3.根据权利要求1或2所述的吖啶衍生物,其特征在于,所述R’、R”、R5各自独立地选自甲基、乙基、环戊基、环己基、取代或未取代的C6-C60芳基、或者取代或未取代的C2-C60杂环芳基组成的群组;优选地,R’、R”、R5各自独立地选自甲基、苯基或芴基;
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芳胺基组成的群组;优选地,Ar1、Ar2各自独立地选自苯基、联苯基、萘基、芴基、菲基、三亚苯基;
Ar3、Ar4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、R6、R7、R8、R9、R10、R11、R12各自独立地选自由氢、氟、腈基、甲基、乙基、叔丁基、取代或未取代的C6-C60芳基、取代或未取代的C2-C60杂环芳基组成的群组;优选地,R1、R2、R3、R4、R6、R7、R8、R9、R10、R11、R12各自独立地选自氢、甲基或叔丁基;R1、R2、R3、R4、R6、R7、R8、R9、R10、R11、R12中至少有一者为式(II)所示的基团。
4.根据权利要求1~3任一项所述的吖啶衍生物,其特征在于,所述R’、R”、R5各自独立地为甲基或苯基;Ar1、Ar2各自独立地选自苯基、联苯基、萘基;
R1、R2、R3、R4、R6、R7、R8、R9、R10、R11、R12各自为氢或式(II)所示的基团,并且至少有一个为式(II)所示的基团。
5.根据权利要求1-4任一项所述的吖啶衍生物,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、CRxRy或NAr5;
Rx、Ry为甲基、苯基或芴基;
Ar5为甲基、乙基、苯基或萘基;
7.一种有机电致发光材料,其特征在于,其原料包括权利要求1-6任一项所述的吖啶衍生物。
8.权利要求1-6任一项所述的吖啶衍生物在制备有机电致发光元件中的应用。
9.一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1-6任一项所述的吖啶衍生物。
10.根据权利要求9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。
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