CN112794833A - 一种蓝光染料化合物及其应用 - Google Patents
一种蓝光染料化合物及其应用 Download PDFInfo
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- CN112794833A CN112794833A CN201911112691.3A CN201911112691A CN112794833A CN 112794833 A CN112794833 A CN 112794833A CN 201911112691 A CN201911112691 A CN 201911112691A CN 112794833 A CN112794833 A CN 112794833A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 121
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- 239000010410 layer Substances 0.000 claims description 92
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 44
- 239000000463 material Substances 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 239000001045 blue dye Substances 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 16
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- 125000005843 halogen group Chemical group 0.000 claims description 11
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- 238000003756 stirring Methods 0.000 description 10
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 9
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- 238000001816 cooling Methods 0.000 description 7
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- 239000003054 catalyst Substances 0.000 description 6
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Abstract
Description
技术领域
本发明涉及有机电致发光技术领域。更具体地,涉及一种蓝光染料化合物及其应用。
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。因此设计合成综合性能优良的蓝光材料,将成为有机电致发光材料研究的重要课题。
发明内容
基于以上事实,本发明的第一个目的在于提供一种蓝色染料化合物,其发光为深蓝色且发光效率高。
本发明的第二个目的在于提供一种有机电致发光装置。
本发明的第三个目的在于提供如上第一个目的所述的蓝色染料化合物在制备有机电致发光装置中的应用。
本发明的第四个目的在于提供一种有机电致发光材料。
本发明的第五个目的在于提供如上第一个目的所述的蓝色染料化合物在制备有机电致发光材料中的应用。
为达到上述第一个目的,本发明采用下述技术方案:
一种蓝光染料化合物,其结构通式如式I所示:
其中:
R1、R2在每次出现时相同或不同地选自氢、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5-60个原子的芳香族环系或杂芳蔟环系组成的组,前述基团中的每个可被一个或多个基团R取代;
Ar1、Ar2、Ar3、Ar4在每次出现时相同或不同地选自具有5-60个原子的芳香族环系或杂芳族环系组成的组,所述环系可被一个或多个基团R取代;
L表示单键、-B(R’)-、-N(R’)-、-P(R’)-、-O-、-S-、-Se-、-S(=O)-、-S(O2)-、-C(R’R”)-、-Si(R’R”)-或-Ge(R’R”)-;并且R’、R”各自独立地选自C1-C40链烷基、C2-C40链烯基、C2-C40炔基、C1-C40烷氧基、C3-C40环烷烃基、C3-C40环烯烃基、C6-C60芳基、含有C1-C10烷基的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芳硫基中的任意一种;R’、R”可以任选稠合或接合形成环,并且所述基团中的每个可以被一个或多个基团R取代;
任意两个相邻的基团W代表下式(1)基团,两个相邻的基团K代表下式(2)基团,
其中,G代表C(R)2、NR、氧或硫,Z在每次出现时相同或不同地代表CR或N,或者两个相邻的基团Z代表式(1)或式(2),并且^指示式(1)或(2)中的相应的相邻基团W或K;
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(Ar5)2、N(R3)2、C(=O)Ar5、C(=O)R3、P(=O)(Ar5)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、优选5至60个原子的芳族环或杂芳蔟环系、具有5至60个原子的芳氧基或杂芳氧基组成的组,所述基团中的每个可被一个或多个基团R3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R3C=CR3、C≡C、Si(R3)2、Ge(R3)2、Sn(R3)2、C=O、C=S、C=Se、C=NR3、P(=O)(R3)、SO、SO2、NR3、O、S或CONR3代替,并且其中一个或多个氢原子或被氘原子、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、芳族或杂芳族环系,所述环系可被一个或多个基团R3取代;
R3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(Ar5)2、N(R4)2、C(=O)Ar5、C(=O)R4、P(=O)(Ar5)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60个原子的芳族环或杂芳蔟环系、具有5至60个原子的芳氧基或杂芳氧基组成的组,所述基团中的每个可被一个或多个基团R4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R4C=CR4、C≡C、Si(R4)2、Ge(R4)2、Sn(R4)2、C=O、C=S、C=Se、C=NR4、P(=O)(R4)、SO、SO2、NR4、O、S或CONR4代替,并且其中一个或多个氢原子可被氘原子、卤素原子、腈基或硝基代替,其中两个或更多个相邻的取代基R可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系,所述环系可被一个或多个基团R4取代;
Ar5在每次出现时相同或不同地是具有5-30个原子的芳族或杂芳族环系,所述环系可被一个或多个非芳族基团R4取代;此处键合至同一氮原子或磷原子的两个基团Ar5也可通过单键或选自N(R4)、C(R4)2、氧或硫的桥连基彼此桥连;
R4选自氢原子、氘原子、氟原子、腈基、具有C1-C20的脂族烃基、具有5-30个原子的芳族环或杂芳族环系,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取代基R4可彼此形成单环或多环的脂族、芳族或杂芳族环系。
进一步地,所述式I主要包含以下式(3)~(8)组成的组:
其中,R1、R2、Ar1、Ar2、Ar3、Ar4、L、G的含义具有如上定义给出的相同的含义。
本发明意义上的芳基含有6-60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。
在本发明意义上的芳族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。
对于本发明意义上的含有1~40个碳原子并且其中单独的氢原子或-CH2-基团还可被上述基团取代的脂族烃基或者烷基或者烯基或炔基优选被认为是指如下基团:甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、新戊基、环戊基、正己基、新己基、环己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、环己烯基、庚烯基、环庚烯基、辛烯基、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基或辛炔基。烷氧基优选具有1-40个碳原子的烷氧基被认为是指甲氧基、三氟甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、仲戊氧基、2-甲基丁氧基、正己氧基、环己氧基、正庚氧基、环庚氧基、正辛氧基、环辛氧基、2-乙基己氧基、五氟乙氧基和2,2,2-三氟乙氧基。杂烷基优选具有1-40个碳原子的烷基,是指其中单独的氢原子或-CH2-基团可被氧、硫、卤素原子取代的基团,被认为是指烷氧基、烷硫基、氟代的烷氧基、氟代的烷硫基,特别是指甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、三氟甲硫基、三氟甲氧基、五氟乙氧基、五氟乙硫基、2,2,2-三氟乙氧基、2,2,2-三氟乙硫基、乙烯氧基、乙烯硫基、丙烯氧基、丙烯硫基、丁烯硫基、丁烯氧基、戊烯氧基、戊烯硫基、环戊烯氧基、环戊烯硫基、己烯氧基、己烯硫基、环己烯氧基、环己烯硫基、乙炔氧基、乙炔硫基、丙炔氧基、丙炔硫基、丁炔氧基、丁炔硫基、戊炔氧基、戊炔硫基、己炔氧基、己炔硫基。
一般来说,根据本发明的环烷基、环烯基可为环丙基、环丁基、环戊基、环己基、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。
根据本发明的芳族或杂芳族环原子,在每种情况下还可被上述基团R4取代的芳族或杂芳族环系,特别是指衍生自如下物质的基团:苯、萘、蒽、苯并蒽、菲、芘、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。
进一步地,所述式I所示的化合物主要包括以下式SLC-B421~SLC-B621所示的结构:
其中,G在每次出现时相同或不同地选自C(CH3)2、O或S。
为达到上述第二个目的,本发明提供一种如上第一个目的所述的蓝光染料化合物在制备有机电致发光材料中的应用。
为达到上述第三个目的,本发明提供有机电致发光材料,所述材料由如上第一个目的所述的蓝光染料化合物制备得到。
有机电致发光材料可以单独使用本发明的蓝光染料化合物构成,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蓝光染料化合物可以用作但不限于空穴注入材料、空穴传输材料或荧光发光材料。
为达到上述第四个目的,本发明提供一种有机电致发光装置,所述有机电致发光装置包括第一电极、第二电极和置于所述第一电极、所述第二电极之间的一个或多个有机层,所述一个或多个有机层包含如上第一个目的所述的蓝光染料化合物中的一种或多种。
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。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,如在例如WO2005053051中所述的。
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,其特征在于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,其特征在于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,其特征在于借助于升华方法来施加至少一个层,和/或特征在于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/或特征在于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蓝光染料化合物。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蓝光染料化合物。特别是,所述蓝光染料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蓝光染料化合物,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。
进一步地,所述有机层还包括选自电子注入层、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、发光层的一种以上。
进一步地,所述掺杂物与主发光体的质量比为1:99~50:50。
为达到上述第五个目的,本发明提供一种如上第一个目的所述的蓝光染料化合物在制备有机电致发光装置中的应用。
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。
本发明的有益效果如下:
本发明提供的蓝光染料化合物是一系列具有螺芴结构的新型有机电致发光化合物,是在螺芴分子的一侧引入苯并萘和苯并呋喃或苯并噻吩或苯并芴、增大分子空间位阻的同时,增大分子内的电子密度,减弱分子间的π-π相互作用,使有机分子在低温下也可以进行升华、蒸镀以及进行溶液工序,并且具有与以住的化合物相比更短的发光波长。提高有机分子的稳定性和在有机溶媒中的溶解性;同时,该蓝光染料化合物阻碍有机分子间激-激复合物的生成、增加内部电子密度和稳定性,由此得以提高包含该化合物的有机电致发光器件的效率、寿命;此外,此外,该蓝光染料化合物改善对溶液的溶解度而解决以往蓝光掺杂物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
下面结合附图对本发明的具体实施方式作进一步详细的说明。
图1示出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示出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。
图1、图2中,有机电致发光装置具有基板1、阳极2、阴极8,以及配置于阳极2与阴极8之间的层3~7。其中,在阴极8与发光层5之间配置有空穴阻挡/电子传输层6和电子注入层7,在发光层5与阳极2之间配置有空穴注入3和空穴传输/电子阻挡层4。
具体实施方式
为了更清楚地说明本发明,下面结合优选实施例和附图对本发明做进一步的说明。附图中相似的部件以相同的附图标记进行表示。本领域技术人员应当理解,下面所具体描述的内容是说明性的而非限制性的,不应以此限制本发明的保护范围。
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,例如苯硼酸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;
寿命测试:使用LTS-1004AC寿命测试装置。
实施例1
化合物SLC-B557的制备方法,包括如下步骤:
第一步:化合物Int-1的制备
在氮气保护下,7.65g(37.5mmol)的2-溴-3-甲氧基苯酚溶于120ml干燥的二氯甲烷中,加入5.75ml的三乙胺,用液氮降温至-78℃,缓慢滴加入6.94ml的三氟甲烷磺酸酐,搅拌反应半小时,升温至0℃搅拌反应1小时,加入50ml的饱和氯化铵水溶液,搅拌反应30分钟,分出有机相,水相用二氯甲烷萃取,收集有机相干燥,过滤,滤液减压浓缩干,得到11.9g黄色油状物。
加入10.35g(75.0mmol)的无水碳酸钾、12.5g(41.2mmol)的(2-((异丙基硅基)乙炔基)苯基)硼酸,再加入526.5mg(0.75mmol)的PdCl2(PPh3)2催化剂以及80ml的乙醇和20ml的水,加热升温至90℃搅拌反应12小时,冷却到室温,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10.0g黄色油状物。
第二步:化合物Int-2的制备
在氮气保护下,10.0g(22.5mmol)第一步制备的Int-1溶于100ml干燥的THF中,滴加入33.75ml的1M的TBAF四氢呋喃溶液,搅拌反应12小时,加入50ml的水,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,用硅胶柱分离纯化,得到黄色固体Int-2,收率76%。
第三步:化合物Int-3的制备
取5.0g(17.4mmol)第二步制备的中间体Int-2与80ml的甲苯混合,在氮气保护下,加入0.46g(1.74mmol)的二氯化钯,升温至80℃搅拌反应24小时,冷却到室温,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到黄色固体Int-3,收率72%。
第四步:化合物Int-4的制备
5.0g(17.4mmol)第三步制备的中间体Int-3、20.9mmol的二苯并[b,d]呋喃-4-硼酸或二苯并[b,d]噻吩-4-硼酸或(9,9-二甲基-9H-芴基-1-基)硼酸、7.4g(69.6mmol)的无水碳酸钠和0.1g(0.086mmol)的Pd(PPh3)4催化剂混合,再加入80ml的甲苯、40ml的乙醇和30ml的水,在氮气保护下,加热回流反应12小时,冷却到室温,加入30ml的水稀释,用二氯甲烷萃取,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,收率>80%。
第五步:化合物Int-5的制备
13.0mmol第四步制备的中间体Int-4溶于80ml的二氯甲烷,在氮气保护下,用冰水浴降温至0℃,滴加入19.5ml的1M的三溴化硼-二氯甲烷溶液,搅拌反应1小时,升到室温搅拌反应2小时,加入30ml的盐水稀释,用二氯甲烷萃取,收集有机相,干燥,过滤,滤液减压浓缩干,得到褐色固体。
在氮气保护下,将制备的得到的褐色固体溶于120ml干燥的二氯甲烷中,加入5.75ml的三乙胺,用液氮降温至-78℃,缓慢滴加入6.94ml的三氟甲烷磺酸酐,搅拌反应半小时,升温至0℃搅拌反应1小时,加入50ml的饱和氯化铵水溶液,搅拌反应30分钟,分出有机相,水相用二氯甲烷萃取,收集有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,收率>75%。
第六步:化合物Int-6的制备
10.0mmol第五步制备的中间体Int-5溶于80ml的N,N-二甲基甲酰胺中,加入224.5mg(1.0mmol)的醋酸钯,升温至100℃,分批加入3.3g(10.0mmol)的铁氰化钾固体,搅拌反应12小时,冷却到室温,加入100ml的饱和盐水稀释,过滤,滤饼用水洗,再用硅胶柱分离纯化,得到黄色固体。
第七步:化合物Int-7的制备
13.1mmol第六步制备的中间体Int-6分散于60ml的水中,加入1.75g(26.2mmol)的氢氧化钾,升温回流搅拌反应12小时,冷却到室温,滴加入稀盐酸调至酸性,过滤,滤饼用水洗,得到白色固体。
第八步:化合物Int-8的制备
37.6mmol第七步制备的中间体Int-7分散于150ml的甲烷磺酸中,升温至80℃搅拌反应6小时,冷却到室温,将反应液滴加入冰水中,过滤,滤饼用水洗、乙醇洗,得到黄色固体,收率>72%。
第九步:化合物Int-9的制备
26.3mmol第八步制备的中间体Int-8分散于100ml的33%溴化氢冰醋酸溶液中,升温至60℃,滴加入8.5g(52.6mmol)的溴素,搅拌反应6小时,冷却到室温,将反应液滴加入冰水中,过滤,滤饼用水洗、乙醇洗,再用硅胶柱分离纯化,得到黄色固体。
第十步:化合物Int-10的制备
在氮气保护下,5.0g(21.4mmol)的2-溴联苯溶解于150ml的干燥THF中,用液氮降温至-78℃,滴加入8.6ml的2.5M正丁基锂-己烷溶液,搅拌反应1小时,分批加入20.0mmol上步制备的中间体Int-9,搅拌反应2小时,升到室温,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,得到深黄色的固体。
加入100ml的冰醋酸和2ml的浓硫酸,升温回流搅拌反应5小时,冷却到室温,过滤,滤饼用水洗,乙醇洗,再用硅胶柱分离纯化,得到黄色固体。
第十一步:化合物SLC-B557的制备
将第十步制备的5mmol化合物Int-10分散在60ml的甲苯中,加入12.5mmol的4,4’-二甲基二苯基胺,再加入1.5g(15.0mmol)的叔丁醇钠、55.0mg(0.05mmol)的Pd2(dba)3催化剂和0.1ml的10%叔丁基磷甲苯溶液,升温至100℃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,再用二氯甲烷和丙酮重结晶,得到SLC-B557,黄色固体,MS(MALDI-TOF):m/z G=C(CH3)2,923.4373[M+H]+;G=O,896.3748[M+];G=S,912.3517[M+]。
实施例2
化合物SLC-B534的制备:
参照实施例1的制备方法,仅将实施例1中第四步的二苯并[b,d]呋喃-4-硼酸或二苯并[b,d]噻吩-4-硼酸或(9,9-二甲基-9H-芴基-1-基)硼酸替换为二苯并[b,d]呋喃-1-硼酸或二苯并[b,d]噻吩-1-硼酸或(9,9-二甲基-9H-芴基-4-基)硼酸,制备中间体Int-11,将实施例1中第十一步的中间体Int-10替换为Int-11,将实施例1中第十一步的4,4’-二甲基二苯基胺替换为4,4’-二叔丁基二苯基胺,制备化合物SLC-B534,黄色固体,MS(MALDI-TOF):m/z G=C(CH3)2,1090.6147[M+];G=O,1065.5749[M+H]+;G=S,1080.5402[M+]。
实施例3
化合物SLC-B532、SLC-B533、SLC-B535~SLC-B556、SLC-B558~SLC-B603的制备:
参照实施例1和实施例2的制备方法,将实施例1第十一步中的4,4’-二甲基二苯基胺替换为相应取代的芳胺,或将实施例2中的4,4’-二叔丁基二苯基胺替换为相应取代的芳胺制备目标化合物SLC-B532、SLC-B533、SLC-B535~SLC-B556、SLC-B558~SLC-B603。
实施例4
化合物SLC-B457的制备方法,包括如下步骤:
第一步:化合物Int-12的制备
在氮气保护下,4.85g(25.0mmol)的2-菲酚溶于80ml干燥的乙腈中,用液氮降温至-18℃,缓慢滴加入4.2g(27.5mmol)的三氟甲烷磺酸,搅拌反应半小时,分批加入4.9g(27.5mmol)的NBS,搅拌反应1小时,升到室温搅拌反应12小时,加入50ml的饱和亚硫酸氢钠水溶液,搅拌反应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,用硅胶柱分离纯化,得到白色固体,收率74%。
第二步:化合物Int-13的制备
5.0g(18.3mmol)第一步制备的中间体Int-12、21.9mmol的二苯并[b,d]呋喃-4-硼酸或二苯并[b,d]噻吩-4-硼酸或(9,9-二甲基-9H-芴基-1-基)硼酸、10.4g(73.2mmol)的无水碳酸钾和0.1g(0.086mmol)的Pd(PPh3)4催化剂混合,再加入80ml的甲苯、40ml的乙醇和30ml的水,在氮气保护下,加热回流反应12小时,冷却到室温,加入30ml的水稀释,用二氯甲烷萃取,收集有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到褐色固体,收率>75%。
第三步:化合物Int-14的制备
在氮气保护下,将第二步制备的12.0mmol褐色固体溶于120ml干燥的二氯甲烷中,加入5.75ml的三乙胺,用液氮降温至-78℃,缓慢滴加入6.94ml的三氟甲烷磺酸酐,搅拌反应半小时,升温至0℃搅拌反应1小时,加入50ml的饱和氯化铵水溶液,搅拌反应30分钟,分出有机相,水相用二氯甲烷萃取,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。
第四步:化合物Int-15的制备
参照实施例1中第六步的制备方法,将实施例1中第六步的中间体Int-5替换为上步制备的中间体Int-14,制备中间体Int-15,黄色固体。
第五步:化合物Int-16的制备
参照实施例1中第七步的制备方法,将实施例1中第七步的中间体Int-6替换为上步制备的中间体Int-15,制备中间体Int-16,黄色固体。
第六步:化合物Int-17的制备
参照实施例1中第八步的制备方法,将实施例1中第八步的中间体Int-7替换为上步制备的中间体Int-16,制备中间体Int-17,黄色固体。
第七步:化合物Int-18的制备
参照实施例1中第九步的制备方法,将实施例1中第九步的中间体Int-8替换为上步制备的中间体Int-17,制备中间体Int-18,黄色固体。
第八步:化合物Int-19的制备
参照实施例1中第十步的制备方法,将实施例1中第十步的中间体Int-9替换为上步制备的中间体Int-18,制备中间体Int-19,黄色固体。
第九步:化合物SLC-B457的制备
参照实施例1中第十一步的制备方法,将实施例1中第十一步的中间体Int-10替换为上步制备的中间体Int-19,将实施例1中第十一步的4,4’-二甲基二苯基胺替换为N-(4-叔丁基苯基)二苯并[b,d]呋喃-4-胺或N-(4-叔丁基苯基)二苯并[b,d]噻吩-4-胺或N-(4-叔丁基苯基)-9,9-二甲基-9H-芴-1-胺,得到SLC-B457,黄色固体,MS(MALDI-TOF):m/z G=C(CH3)2、G1=C(CH3)2,1210.6142[M+];G=O、G1=C(CH3)2,1185.5747[M+H]+;G=S、G1=C(CH3)2,1201.5520[M+H]+;G=C(CH3)2、G1=O,1159.5228[M+H]+;G=C(CH3)2、G1=S,1190.4642[M+];G=O、G1=O,1133.4690[M+H]+;G=O、G1=S,1165.4249[M+H]+;G=S、G1=O,1149.4478[M+H]+;G=S、G1=S,1181.4022[M+H]+。
实施例5
化合物SLC-B421~SLC-B456、SLC-B458~SLC-B480的制备:
参照实施例4的制备方法,将实施例4第九步中的N-(4-叔丁基苯基)二苯并[b,d]呋喃-4-胺或N-(4-叔丁基苯基)二苯并[b,d]噻吩-4-胺或N-(4-叔丁基苯基)-9,9-二甲基-9H-芴-1-胺替换为相应取代的二芳胺制备目标化合物SLC-B421~SLC-B456、SLC-B458~SLC-B480。
实施例6
化合物SLC-B510的制备方法,包括如下步骤:
第一步:化合物Int-20的制备
在氮气保护下,19.6g(58.3mmol)的1,4-二溴蒽溶解于100ml的干燥THF中,用液氮降温至-78℃,滴加入25.7ml的2.5M正丁基锂-己烷溶液,搅拌反应1小时,滴加入9.1g(87.5mmol)的硼酸三甲酯,升到室温搅拌反应2小时,加入100ml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,用石油醚分散,过滤,得到白色的固体,收率82%。
第二步:化合物Int-21的制备
13.5g(45.0mmol)第一步制备的中间体Int-20、37.5mmol的1-碘二苯并[b,d]呋喃-2-酚或1-碘二苯并[b,d]噻吩-2-酚或4-溴-9,9-二甲基-9H-芴-3-酚、24.8g(180.0mmol)的无水碳酸钾和520.0mg(0.45mmol)的Pd(PPh3)4催化剂混合,再加入80ml的甲苯、40ml的乙醇和40ml的水,在氮气保护下,升温回流反应12小时,冷却到室温,加入30ml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,收率>60%。
第三步:化合物Int-22的制备
178.0mmol第二步制备的中间体Int-21溶于1200ml的二氯甲烷中,加入28.0g(356.0mmol)的吡啶,用冰水浴降温至0℃,滴加入65.2g(231.0mmol)的三氟甲烷磺酸酐,升到室温搅拌反应12小时,加入500ml的水,分出有机相,水相用二氯甲烷萃取,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,收率>80%。
第四步:化合物Int-23的制备
10.0mmol第三步制备的中间体Int-22溶于80ml的N-甲基-2-吡咯烷酮中,加入22.5mg(0.1mmol)的醋酸钯,升温至140℃,分批加入3.3g(10.0mmol)的铁氰化钾固体,搅拌反应5小时,冷却到室温,加入100ml的饱和盐水稀释,过滤,滤饼用水洗,再用硅胶柱分离纯化,得到黄色固体。
第五步:化合物Int-24的制备
参照实施例1中第七步的制备方法,将实施例1中第七步的中间体Int-6替换为上步制备的中间体Int-23,制备中间体Int-24,黄色固体。
第六步:化合物Int-25的制备
参照实施例1中第八步的制备方法,将实施例1中第八步的中间体Int-7替换为上步制备的中间体Int-24,制备中间体Int-25,黄色固体,收率>40%。
第七步:化合物Int-26的制备
20.0mmol第六步制备的中间体Int-25溶于350ml的二氯甲烷中,于室温下,滴加入3.2g(20.0mmol)的溴素溶于二氯甲烷的溶液,搅拌反应12小时,加入50ml的饱和亚硫酸氢钠水溶液,分出有机相,水相用二氯甲烷萃取,收集有机相,干燥,过滤,滤液减压浓缩干,再用硅胶柱分离纯化,得到黄色固体。
第八步:化合物Int-27的制备
参照实施例1中第十步的制备方法,将实施例1中第十步的中间体Int-9替换为上步制备的中间体Int-26,制备中间体Int-27,黄色固体。
第九步:化合物SLC-B510的制备
参照实施例1中第十一步的制备方法,将实施例1中第十一步的中间体Int-10替换为上步制备的中间体Int-27,将实施例1中第十一步的4,4’-二甲基二苯基胺替换为4,4’-二叔丁基二苯基胺,得到SLC-B510,黄色固体,MS(MALDI-TOF):m/z G=C(CH3)2,1090.6143[M+];G=O,1064.5617[M+];G=S,1080.5404[M+]。
实施例7
化合物SLC-B481~SLC-B509、SLC-B511~SLC-B531的制备:
参照实施例6的制备方法,将实施例6中第九步的4,4’-二叔丁基二苯基胺替换为相应取代的芳胺,制备化合物SLC-B481~SLC-B509、SLC-B511~SLC-B531。
实施例8
化合物SLC-B604的制备方法,包括如下步骤:
第一步:化合物Int-27的制备
在氮气保护下,10.0mmol的1-碘-2-苯氧基苯或1-碘-2-苯硫基苯或1-碘-2-(2-苯基丙基-2-基)苯溶解于100ml的干燥THF中,用液氮降温至-78℃,滴加入4.0ml的2.5M正丁基锂-己烷溶液,搅拌反应1小时,分批加入10.0mmol的中间体Int-11,搅拌反应2小时,升到室温,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,得到深黄色的固体。
加入80ml的冰醋酸和1ml的浓硫酸,升温回流搅拌反应5小时,冷却到室温,过滤,滤饼用水洗,乙醇洗,再用硅胶柱分离纯化,得到中间体Int-27。
第二步:化合物SLC-B604的制备
将上制备的5mmol化合物Int-27分散在60ml的甲苯中,加入12.5mmol的对叔丁基苯基苯胺,再加入1.5g(15.0mmol)的叔丁醇钠、55.0mg(0.05mmol)的Pd2(dba)3催化剂和0.1ml的10%叔丁基磷甲苯溶液,升温至100℃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,再用二氯甲烷和丙酮重结晶,得到SLC-B604,黄色固体,MS(MALDI-TOF):m/z G=C(CH3)2、G1=C(CH3)2,1020.5357[M+];G=O、G1=C(CH3)2,995.4966[M+H]+;G=S、G1=C(CH3)2,1011.4736[M+H]+;G=C(CH3)2、G1=O,995.4964[M+H]+;G=C(CH3)2、G1=S,1011.4722[M+H]+;G=O、G1=O,969.4448[M+H]+;G=O、G1=S,985.4217[M+H]+;G=S、G1=O,985.4215[M+H]+;G=S、G1=S,1001.3969[M+H]+。
实施例9
化合物SLC-B605~SLC-B620的制备:
参照实施例8的制备方法,将实施例8中第一步的1-碘-2-苯氧基苯或1-碘-2-苯硫基苯或1-碘-2-(2-苯基丙基-2-基)苯替换为10-(2-溴苯基)-10H-吩噁嗪或10-(2-溴苯基)-10H-吩噻嗪或10-(2-溴苯基)-9,9-二甲基-9,10-二氢吖啶,制备化合物SLC-B605~SLC-B620。
实施例10
一种OLED元件,如图1所示,上述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
4)在电子阻挡层上继续蒸镀一层本发明的式I所示的蓝光染料化合物和ADN作为有机发光层,其中,ADN为主体材料和本发明的式I所示的蓝光染料化合物为掺杂材料,式I所示的蓝光染料化合物在ADN中的掺杂浓度为5%,蒸镀膜厚为
按照与上相同的步骤,仅将步骤4)所用式I所示的蓝光染料化合物具体为化合物SLC-B425,得到本发明提供的元件OLED-1;
按照与上相同的步骤,仅将步骤4)所用式I所示的蓝光染料化合物具体为化合物SLC-B455,得到本发明提供的元件OLED-2;
按照与上相同的步骤,仅将步骤4)所用式I所示的蓝光染料化合物具体为化合物SLC-B457,得到本发明提供的元件OLED-3;
按照与上相同的步骤,仅将步骤4)所用式I所示的蓝光染料化合物具体为化合物SLC-B488,得到本发明提供的元件OLED-4;
按照与上相同的步骤,仅将步骤4)所用式I所示的蓝光染料化合物具体为化合物SLC-B510,得到本发明提供的元件OLED-5;
按照与上相同的步骤,仅将步骤4)所用式I所示的蓝光染料化合物具体为化合物SLC-B534,得到本发明提供的元件OLED-6;
按照与上相同的步骤,仅将步骤4)所用式I所示的蓝光染料化合物具体为化合物SLC-B557,得到本发明提供的元件OLED-7;
按照与上相同的步骤,仅将步骤4)所用式I所示的蓝光染料化合物具体为化合物SLC-B604,得到本发明提供的元件OLED-8;
按照与上相同的步骤,仅将步骤4)所用式I所示的蓝光染料化合物改为化合物BD01,得到对比元件OLED-9;
对比化合物BD01的结构为:
所得元件OLED-1至OLED-9的性能检测结果如表1所示:
表1性能检测结果
上述实施例10中使用的化合物结构如下:
上述表中,在电流密度为10mA/cm2条件下的驱动电压、半峰宽FWHM、外量子效率EQE以及在亮度为1000cd/m2初始条件下的器件寿命LT90%的数据是针对比较化合物BD01归一化。
结论:从性能测试结果表1可以看到,本发明的化合物作为蓝光染料相较于采用BD01作为蓝光掺杂材料的有机电致发光器件,色度坐标从0.141,0.154降低到了0.14以下,0.13以下,色纯度大大的提高,获得了深蓝光器件,元件的外量子效率超过了目前己知的蓝光材料,而且器件亮度在1000cd/m2的条件下,器件的LT90%寿命也有了相当大的提高。
产业上的应用可能性
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。
显然,本发明的上述实施例仅仅是为清楚地说明本发明所作的举例,而并非是对本发明的实施方式的限定,对于所属领域的普通技术人员来说,在上述说明的基础上还可以做出其它不同形式的变化或变动,这里无法对所有的实施方式予以穷举,凡是属于本发明的技术方案所引伸出的显而易见的变化或变动仍处于本发明的保护范围之列。
Claims (10)
1.一种蓝光染料化合物,其特征在于,所述化合物的结构通式如式I所示:
其中:
R1、R2在每次出现时相同或不同地选自氢、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5-60个原子的芳香族环系或杂芳蔟环系组成的组,前述基团中的每个可被一个或多个基团R取代;
Ar1、Ar2、Ar3、Ar4在每次出现时相同或不同地选自具有5-60个原子的芳香族环系或杂芳族环系组成的组,所述环系可被一个或多个基团R取代;
L表示单键、-B(R’)-、-N(R’)-、-P(R’)-、-O-、-S-、-Se-、-S(=O)-、-S(O2)-、-C(R’R”)-、-Si(R’R”)-或-Ge(R’R”)-;并且R’、R”各自独立地选自C1-C40链烷基、C2-C40链烯基、C2-C40炔基、C1-C40烷氧基、C3-C40环烷烃基、C3-C40环烯烃基、C6-C60芳基、含有C1-C10烷基的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芳硫基中的任意一种;R’、R”可以任选稠合或接合形成环,并且所述基团中的每个可以被一个或多个基团R取代;
任意两个相邻的基团W代表下式(1)基团,两个相邻的基团K代表下式(2)基团,
其中,G代表C(R)2、NR、氧或硫,Z在每次出现时相同或不同地代表CR或N,或者两个相邻的基团Z代表式(1)或式(2),并且^指示式(1)或(2)中的相应的相邻基团W或K;
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(Ar5)2、N(R3)2、C(=O)Ar5、C(=O)R3、P(=O)(Ar5)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、优选5至60个原子的芳族环或杂芳蔟环系、具有5至60个原子的芳氧基或杂芳氧基组成的组,所述基团中的每个可被一个或多个基团R3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R3C=CR3、C≡C、Si(R3)2、Ge(R3)2、Sn(R3)2、C=O、C=S、C=Se、C=NR3、P(=O)(R3)、SO、SO2、NR3、O、S或CONR3代替,并且其中一个或多个氢原子或被氘原子、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、芳族或杂芳族环系,所述环系可被一个或多个基团R3取代;
R3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(Ar5)2、N(R4)2、C(=O)Ar5、C(=O)R4、P(=O)(Ar5)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60个原子的芳族环或杂芳蔟环系、具有5至60个原子的芳氧基或杂芳氧基组成的组,所述基团中的每个可被一个或多个基团R4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R4C=CR4、C≡C、Si(R4)2、Ge(R4)2、Sn(R4)2、C=O、C=S、C=Se、C=NR4、P(=O)(R4)、SO、SO2、NR4、O、S或CONR4代替,并且其中一个或多个氢原子可被氘原子、卤素原子、腈基或硝基代替,其中两个或更多个相邻的取代基R可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系,所述环系可被一个或多个基团R4取代;
Ar5在每次出现时相同或不同地是具有5-30个原子的芳族或杂芳族环系,所述环系可被一个或多个非芳族基团R4取代;此处键合至同一氮原子或磷原子的两个基团Ar5也可通过单键或选自N(R4)、C(R4)2、氧或硫的桥连基彼此桥连;
R4选自氢原子、氘原子、氟原子、腈基、具有C1-C20的脂族烃基、具有5-30个原子的芳族环或杂芳族环系,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取代基R4可彼此形成单环或多环的脂族、芳族或杂芳族环系。
4.一种如权利要求1-3任一项所述的蓝光染料化合物在制备有机电致发光材料中的应用。
5.一种有机电致发光材料,其特征在于,所述材料由如权利要求1-3任一项所述的蓝光染料化合物制备得到。
6.一种有机电致发光装置,其特征在于,所述有机电致发光装置包括第一电极、第二电极和置于所述第一电极、所述第二电极之间的一个或多个有机层,所述一个或多个有机层包含权利要求1-3任一项所述的蓝光染料化合物中的一种或多种。
7.根据权利要求6所述的有机电致发光装置,其特征在于,所述有机层还包括选自电子注入层、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、发光层的一种以上。
9.根据权利要求8所述的有机电致发光装置,其特征在于,所述掺杂物与主发光体的质量比为1:99~50:50。
10.一种如权利要求1-3任一项所述的蓝光染料化合物在制备有机电致发光装置中的应用。
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