CN113429302A - 一种萘并芴衍生物、发光材料、发光元件及消费型产品 - Google Patents
一种萘并芴衍生物、发光材料、发光元件及消费型产品 Download PDFInfo
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- CN113429302A CN113429302A CN202110991724.7A CN202110991724A CN113429302A CN 113429302 A CN113429302 A CN 113429302A CN 202110991724 A CN202110991724 A CN 202110991724A CN 113429302 A CN113429302 A CN 113429302A
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- aromatic
- heteroaromatic ring
- naphthofluorene
- radicals
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- 125000003118 aryl group Chemical group 0.000 claims description 49
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Abstract
Description
技术领域
本发明属于有机电致发光材料技术领域,具体涉及一种萘并芴衍生物、发光材料、发光元件及消费型产品。
背景技术
早在1963年,pope等人首先发现了有机化合物单晶蒽的电致发光现象(Pope M,Kal lmann H, Magnante P. Electroluminescence in organic crystals[J].Chem.Phys., 1963,38(8): 2042-2043.),开启了有机电致发光(简称OLED)及相关的研究。经过二十几年的发展,有机发光(简称EL)材料已经全面实现了红、蓝、绿色发光,应用领域也从小分子扩展到了高分子以及金属络合物等领域。
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,但在产业化时程中,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。尤其是发光元件在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,但是金属配合物具有特殊的电子结构特征,导致其蓝光材料无法达到使用要求。
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器件中的工作电压、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。
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,本发明提供了一种萘并芴衍生物、发光材料、发光元件及消费型产品,本发明所述的萘并芴衍生物适用于荧光或磷光OLED中,具有高的热稳定性,且能够在没有分解和没有残余物的情况下进行升华。
为了实现上述目的,本发明采用如下技术方案:
一种萘并芴衍生物,所述的萘并芴衍生物的结构式如式(I)所示:
R1~R2在每次出现时相同或不同地选自由氢原子、氘原子、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的烯基或炔基基团、具有5至80个、优选5至60个碳原子的芳族环或杂芳族环系组成的群组,R1和R2在每种情况下可以被一个或多个基团R取代,或这些基团中的两个、三个、四个或五个的组合,R在每种情况下可以是相同的或不同的,R1和R2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R取代;
R3~R14在每次出现时相同或不同地选自由氢原子、氘原子、具有C1~C40的直链烷基、具有C3~C40的支链或环状的烷基、具有5至80个、优选5至60个碳原子的芳族环或杂芳族环系、或式(II)组成的群组,R3~R14在每种情况下可以被一个或多个基团R取代,或这些基团中的两个、三个、四个或五个的组合,R在每种情况下可以是相同的或不同的,其中两个或更多个相邻的取代基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R取代;并且R13不是氢原子或氘原子;
Ar1、Ar2各自相同或者不同,选自由具有5至60个碳原子的芳族环系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;Ar1和Ar2可以任选地接合或稠合形成单环或多环的芳族或杂芳族环系;
L表示单键、具有5至60个碳原子的亚芳族环系或亚杂芳族环系中的一种或这些基团的组合;
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、Si(R0)3、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,所述基团中的每个可被一个或多个基团R0取代,其中一个或多个非相邻的-CH2-基团可被R0C=CR0、C≡C、Si(R0)2、Ge(R0)2、Sn(R0)2、C=O、C=S、C=Se、C=NR0、P(=O)(R0)、SO、SO2、NR0、O、S或CONR0代替,并且其中一个或多个氢原子可被氘原子、卤素原子或腈基代替,具有5至60个碳原子的芳族环或杂芳族环系、具有5至60个碳原子的芳胺基或杂芳胺基组成的组,其在每种情况下可以是相同的或不同的,其在每种情况下可以被一个或多个基团R0取代,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R0取代;
R0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个碳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,其中任意相邻的两个或多个相邻的R0可彼此形成单环或多环的脂族、芳族或杂芳族环系。
本发明人经过大量的试验发现,所述的衍生物特别是在寿命、效率和工作电压方面在有机电致发光元件中引起了显著的改进。特别是将本发明的化合物用作空穴传输材料或用作基质材料时,这种情况适用于磷光和荧光的电致发光元件。所述材料通常具有高的热稳定性,并且因此能够在没有分解和没有残余物的情况下进行升华。因此,本发明涉及这些材料,并且涉及包含这种类型的化合物的电子元件。特别地,使用芳族单胺获得了非常好的结果,这是令人惊讶的结果,因为含有至少两个氮原子的空穴传输材料通常被用于有机电致发光元件中。
进一步的,所述R1~R2在每次出现时相同或不同地选自由具有C1~C40的直链烷基、具有C3~C40的支链或环状的烷基、具有5至80个、优选5至60个碳原子的芳族环或杂芳族环系组成的群组,R1和R2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;
R3~R14在每次出现时相同或不同地选自由氢原子、氘原子、具有C1~C40的直链烷基、具有C3~C40的支链或环状的烷基、具有5至80个、优选5至60个碳原子的芳族环或杂芳族环系、或式(II)组成的群组,并且R13不是氢原子或氘原子;
Ar1、Ar2各自相同或者不同,选自由具有5至60个碳原子的芳族环系或杂芳族环系组成的群组,Ar1和Ar2可以任选地接合或稠合形成单环或多环的芳族或杂芳族环系;
L表示单键、具有5至60个碳原子的亚芳族环系或亚杂芳族环系中的一种或这些基团的组合;
进一步的,所述基团Ar1和Ar2在每次出现时相同或不同地选自由式(2)~(27)的基团组成的群组:
其中,虚线键指示与N连接的位置。
进一步的,L选自由式(28)至(44)所示的结构组成的群组:
其中,一个虚线键指示与所述萘并芴主体结构的键合,而另一个虚线指示与N的键合。
进一步的,所述基团(28)至(44)中的R特别优选代表为氢。
进一步的,所述R1、R2特别优选代表为甲基、苯基、芴基。
进一步的,基团R13选自由具有C1~C40的直链烷基、具有C3~C40的支链或环状的烷基、具有5至80个、优选5至60个碳原子的芳族环或杂芳族环系、或式(II)组成的群组。
进一步的,基团R13特别优选代表为甲基、乙基、叔丁基、苯基、联苯基。
进一步的,基团R3~R12选自由氢原子、氘原子、具有C1~C40的直链烷基、具有C3~C40的支链或环状的烷基、具有5至80个、优选5至60个碳原子的芳族环或杂芳族环系或具有式(II)基团组成的组,其中两个或更多个相邻的取代基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R取代;
进一步的,所述基团R3~R12特别优选代表为氢。
进一步的,所述式(II)中的基团Ar1、Ar2各自相同或者不同,选自具有5至60个碳原子的芳族环系或杂芳族环系,所述环系可被一个或多个基团R取代;Ar1和Ar2可以任选地接合或稠合形成单环或多环的芳族或杂芳族环系;如果基团R与Ar1或Ar2键合,则所述基团R在每次出现时相同或不同地选自氢原子或氘原子,具有C1~C10的直链烷基基团或具有C3~C10的支链或环状的烷基基团;
进一步的,所述式(II)中的基团L表示单键、具有5至60个碳原子的亚芳族环系或亚杂芳族环系中的一种或这些基团的组合;
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中含有5~60个碳原子,其中从苯、萘、菲、芴、螺二芴、二苯并呋喃和二苯并噻吩或这些基团的组合构建所述芳族环系。本发明意义上的芳族环系特别是还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R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、䓛、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,所述萘并芴衍生物为以下CJHL900~CJHL999、CJHM000~CJHM076所示结构中的一种:
其中,T为*—O—*、*—S—*或下述结构中的一种:
*—和—*表示连接键。
一种有机电致发光材料,包括所述的萘并芴衍生物。
一种有机电致发光元件,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至少一层有机层,所述有机层的至少一层包含所述的萘并芴衍生物。
进一步的,所述的萘并芴衍生物在有机电致发光元件中用作空穴传输层材料、空穴注入层材料、激子阻挡层材料、荧光发光体或磷光发光体的基质材料。
所述有机电致发光元件包含阴极、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。
在本发明的另外的实施方式中,式(I)的化合物或优选的实施方式既可用于空穴传输层或空穴注入层或激子阻挡层,又可用作荧光发光体或磷光发光体的基质材料。
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元件,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,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修饰本发明式(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。
在本发明的另一个实施方式中,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。
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,可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。
这些方法通常为本领域的技术人员所知,并且可由他在没有付出创造性劳动的情况下应用到包含本发明化合物的有机电致发光元件中。
本发明的有机电致发光元件既可以是顶发射光元件,又可以是底发射光元件。本发明的有机电致发光元件的结构和制备方法没有限定。采用本发明的化合物制得的有机电致发光元件可降低启动电压、提高发光效率和亮度。
一种消费型产品,包含所述的有机电致发光元件。
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。
与现有技术相比,本发明的有益效果为:
(1)本发明所述的萘并芴衍生物是在芴母核的基础上并入萘基,增大芴平面的共轭强度,同时引入大位阻的取代基,使分子不易结晶,提高玻璃化转变温度的同时提高分子的热稳定性;
(2)本发明所述的萘并芴衍生物非常适合用于有机电致发光元中的空穴传输或激子阻挡层中,特别是还适用于与磷光发光层直接相邻的层中,这是由于所述的萘并芴衍生物并不湮灭发光;
(3)本发明所述的萘并芴衍生物用作荧光或磷光发光体的基质材料时,具有非常高的效率和长寿命,尤其是所述衍生物与其它基质材料和磷光发光体一起用作基质材料时特别适用这点;
(4)所述的衍生物用于有机电致发光元件中时,具有较高的效率,并且在使用和低工作电压的情况下导致陡峭的电流-电压曲线,本发明所述的衍生物具有高的热稳定性,并且能够在不分解和没有残余物的情况下进行升华,另外具有高的氧化稳定性,对于衍生物的处理和对于溶液的贮存稳定性具有积极的效果。
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是本发明有机电致发光元件一个底部发光例子的示意图;
图2是本发明有机电致发光元件一个底部发光例子的示意图。
附图标记
1-基板、2-阳极、3-空穴注入层、4-空穴传输/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。
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。
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。
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。
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。
本发明的萘并芴衍生物的合成路线,包括如下步骤:
其中X1选自氢、氯、溴、碘;R、R1、R2、R13、R14、Ar1和Ar2的含义如上文所定义。
实施例1
化合物G的制备方法,包括如下步骤:
第一步:化合物A-1的制备
110.0 mmol的三甲基硅基乙炔溶解于80.0 mL干燥的THF中,在氮气保护下,用液氮降温至-78℃,滴加入110.0 mmol的正丁基锂己烷溶液,搅拌反应10分钟,滴加入100.0mmol的2-乙炔基苯甲醛(CAS:38846-64-9)溶于THF的溶液,升至室温搅拌反应1小时,加入20 mL饱和的氯化铵水溶液,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,得到化合物A-1,黄色油状物,收率96%。
第二步:化合物B-1的制备
10.0 mmol的氯化亚铜与6 mL的正丁基氨、14 mL的水混合,在氮气保护下,降温至0℃,加入11.0 mmol的盐酸羟胺,搅拌反应至无色,加入100.0 mmol的中间体A-1溶于二氯甲烷的溶液,搅拌反应5分钟,滴加入150.0 mmol的溴乙炔基苯(CAS:932-87-6)溶于二氯甲烷的溶液,搅拌反应1小时,升到室温,加入50 mL饱和的氯化铵水溶液,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,得到化合物B-1,黄色油状物,收率58%。
第三步:化合物C-1的制备
50.0 mmol的B-1溶于200 mL干燥的二氯甲烷中,加入1.0 mol的二氧化锰固体,于室温搅拌反应5小时,过滤,滤饼用二氯甲烷洗,收集滤液,减压浓缩干燥,用硅胶柱分离纯化,得到黄色固体,收率95%。
第四步:化合物D-1的制备
40.0 mmol的C-1和120.0 mmol的香豆素溶解于120 mL干燥的氯仿中,在氮气保护下,升温回流搅拌反应24小时,冷却至室温,减压浓缩干燥,用硅胶柱分离纯化,得到红色固体,收率47%。
第五步:化合物E-1的制备
50.0 mmol的D-1溶解于150 mL的四氯化碳中,在氮气保护下,降温至0℃,滴加入50.0 mmol的溴素,搅拌反应18小时,加入20 mL的饱和亚硫酸氢钠水溶液,搅拌1小时,分出有机相,水相用二氯甲烷萃取,收集有机相,干燥,过滤,滤液减压浓缩干燥,用硅胶柱分离纯化,得到化合物E-1,红色固体,收率90%。
第六步:化合物F-1的制备
50.0 mmol的E-1溶解于100 mL的二氯甲烷中,在氮气保护下,降温至-5℃,加入0.55 mol的冰醋酸,分批加入125.0 mmol的硼氢化钠,升到室温搅拌反应8小时,加入50 mL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,滤液减压浓缩干燥,用硅胶柱分离纯化,得到化合物F-1,白色固体,收率84%。
第七步:化合物G-1的制备
40.0 mmol的F-1溶解于80 mL的THF中,在氮气保护下,降温至0℃,加入125.0 mol的叔丁醇钾,搅拌反应1小时,加入120.0 mmol的碘甲烷,搅拌反应12小时,加入50 mL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,滤液减压浓缩干燥,用硅胶柱分离纯化,得到化合物G-1,白色固体,收率87%。
参照上述的G-1的合成方法,制备以下化合物:
实施例2
化合物G-17的制备方法,包括如下步骤:
第一步:化合物E-2的制备
50.0 mmol的D-2(参照实施例1的合成方法制备)溶解于100 mL干燥的THF中,滴加入55.0 mmol的四丁基氟化铵THF溶液,于室温搅拌反应2小时,加入100 mL的冰水溶液,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,得到化合物E-2,红色固体,收率100%。
第二步:化合物F-2的制备
45.0 mmol的E-2溶于100 mL干燥的THF中,在氮气保护下,降温至0℃,滴加入54.0mL的1.0M苯基溴化镁THF溶液,搅拌反应1小时,升至室温搅拌反应2小时,滴加入50 mL的2N稀盐酸水溶液,用乙酸乙酯萃取,收集有机相,干燥,减压浓缩干燥,用硅胶柱分离纯化,得到白色固体,收率89%。
第三步:化合物G-17的制备
40.0 mmol的F-2溶解于80 mL干燥的苯中,在氮气保护下,加入40.0 mmol的浓硫酸,升温回流搅拌反应5小时,冷却至室温,滴加入100 mL的饱和碳酸氢钠水溶液,用乙酸乙酯萃取,收集有机相,干燥,减压浓缩干燥,用硅胶柱分离纯化,得到G-17,白色固体,收率86%。
参照上述实施例1和实施例2的合成方法,制备以下化合物:
实施例3
化合物CJHL912的制备:
10.0 mmol的双([1,1'-联苯基]-4-基)胺(CAS:102113-98-4),12.0 mmol的化合物G-1、15.0 mmol的叔丁醇钠,再加入0.05 mmol的Pd2(dba)3CHCl3催化剂、0.05 mL的10%三叔丁基磷甲苯溶液和60 mL的甲苯,在氮气保护下,升温至100℃搅拌反应12小时,冷却到室温,加入50 mL的水稀释,用二氯甲烷萃取,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CJHL912,白色固体,收率84%。
参照上述类似的合成方法,制备以下化合物:
实施例4
化合物CJHL963的制备:
25.0 mmol的N-苯基-[1,1'-联苯基]-4-胺(CAS:32228-99-2),10.0 mmol的化合物G-15、30.0 mmol的叔丁醇钠,再加入0.1 mmol的Pd2(dba)3CHCl3催化剂、0.15 mL的30%三叔丁基磷甲苯溶液和80 mL的甲苯,在氮气保护下,升温至110℃搅拌反应12小时,冷却到室温,加入50 mL的水稀释,用二氯甲烷萃取,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CJHL963,白色固体,收率87%。
参照上述类似的合成方法,制备以下化合物:
实施例5
化合物CJHL976的制备:
10.0 mmol的G-8,12.0 mmol的4-(二苯基胺基)苯硼酸频那醇酯(CAS:267221-88-5)、30.0 mmol的碳酸钠,再加入0.01 mmol的Pd(PPh3)4催化剂和40 mL的甲苯、20 mL的乙醇以及20 mL的水,在氮气保护下,升温回流搅拌反应5小时,冷却到室温,加入50 mL的水稀释,用乙酸乙酯萃取,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CJHL976,白色固体,收率88%。
参照上述类似的合成方法,制备以下化合物:
实施例6
化合物CJHM037的制备,包括如下步骤:
第一步:化合物H-1的制备
20.0 mmol的G-25,24.0 mmol的联硼酸频那醇酯、30.0 mmol无水醋酸钾,再加入0.02 mmol的PdCl2(dppf)催化剂和60 mL的DMF,在氮气保护下,升温至90℃,搅拌反应10小时,冷却到室温,加入100 mL的水稀释,用乙酸乙酯萃取,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H-1,白色固体,收率86%。
第二步:化合物CJHM037的制备
12.0 mmol的H-1,10.0 mmol的2-氯-4,6-二苯基-1,3,5-三嗪(CAS:3842-55-5)、30.0 mmol的碳酸钾,再加入0.01 mmol的Pd(PPh3)4催化剂和40 mL的甲苯、20 mL的乙醇以及20 mL的水,在氮气保护下,升温回流搅拌反应10小时,冷却到室温,加入50 mL的水稀释,用乙酸乙酯萃取,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CJHM037,白色固体,收率82%。
参照上述类似的合成方法,制备以下化合物:
本发明提供的OLED元件如图1和图2所示,该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层3和空穴传输/电子阻挡层4。
对比例1
有机电致发光元件的制备
使用下述的式C所示化合物作为空穴注入层材料、式D所示化合物作为空穴传输层材料、式H所示化合物作为电子阻挡层材料、式A所示化合物作为发光层的绿光主体材料,使用下述的式B所示化合物作为发光层的绿光掺杂材料、式E所示化合物作为发光层的红光主体材料、式F所示化合物作为发光层的红光掺杂材料、式G所示化合物作为电子传输层的掺杂材料、LiQ作为电子传输层的主体材料,如下所述的制备有机电致发光元件。
将化合物C (350Å)/ D (350Å)/ H (1200Å)/ A+B (3%) (300Å)/ LiQ+G (50%)(350Å)/ LiF (10Å)/ Al (2 nm)依次采用DOV公司制造的EL蒸镀机蒸镀到ITO玻璃上制作绿光元件,制得作为绿光对比例1的有机电致发光元件。
将化合物C (350Å)/ D (350Å)/ H (1100Å)/ E+F (3%) (300Å)/ LiQ+G (50%)(350Å)/ LiF (10Å)/ Al (2 nm)依次采用DOV公司制造的EL蒸镀机蒸镀到ITO玻璃上制作红光元件,制得作为红光对比例1的有机电致发光元件。
实施例7
如对比例1中绿光有机电致发光元件制备方法,将所述的化合物H替换为本发明的化合物CJHL900~CJHL999和CJHM000~CJHM076,除此之外,采用同样的方法制作有机电致发光元件:ITO/C (350Å)/D (350Å)/[本发明的化合物](1200Å)/A+B (3%) (300Å)/LiQ+G(50%)(350Å)/LiF (10Å)/Al (2 nm)。
所得元件的性能是在元件亮度在1000尼特条下的测试结果,并且电压、外量子效率(EQE)、电流效率(LE)和衰减寿命LT90%的数据是相对于对比例1元件归一化,所得结果列于表1中。
表1:绿光元件性能检测结果
由上可知,本发明的有机材料制备成的绿光元件驱动电压低,效率较高,色纯度较好,而且在元件发光亮度初始为1000尼特为基准的条件下,使用本发明的化合物作为空穴层材料的元件寿命要好很多。
在对比例1中有机电致发光元件的红光中,将前述的化合物H替换为本发明的化合物CJHL900~CJHL999和CJHM000~CJHM076,除此之外,采用同样的方法制作有机电致发光元件:ITO/C (350Å)/D (350Å)/[本发明的化合物] (1100Å)/E+F (5%) (300Å)/LiQ+G (50%)(350Å)/LiF (10Å)/Al (2 nm)
所得元件的性能是在元件亮度在1000尼特条下的测试结果,并且电压、外量子效率(EQE)、电流效率(LE)和衰减寿命LT90%的数据是相对于对比例元件归一化,所得结果列于表2中。
表2: 红光元件性能检测结果
由表1的绿光元件性能和表2的红光元件性能测试结果可知,本发明的有机材料制备成的元件驱动电压明显降低,效率高,发光色纯度较好,而且在元件发光初始亮度为1000尼特为基准的条件下,使用本发明的化合物作为绿光或红光主体材料的元件寿命衰减要慢很多。
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 (9)
1.一种萘并芴衍生物,其特征在于,所述的萘并芴衍生物的结构式如式(I)所示:
R1~R2在每次出现时相同或不同地选自由氢原子、氘原子、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的烯基或炔基基团、具有5至80个、优选5至60个碳原子的芳族环或杂芳族环系组成的群组,R1和R2在每种情况下可以被一个或多个基团R取代,或这些基团中的两个、三个、四个或五个的组合,R在每种情况下可以是相同的或不同的,R1和R2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R取代;
R3~R14在每次出现时相同或不同地选自由氢原子、氘原子、具有C1~C40的直链烷基、具有C3~C40的支链或环状的烷基、具有5至80个、优选5至60个碳原子的芳族环或杂芳族环系、或式(II)组成的群组,R3~R14在每种情况下可以被一个或多个基团R取代,或这些基团中的两个、三个、四个或五个的组合,R在每种情况下可以是相同的或不同的,其中两个或更多个相邻的取代基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R取代;并且R13不是氢原子或氘原子;
Ar1、Ar2各自相同或者不同,选自由具有5至60个碳原子的芳族环系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;Ar1和Ar2可以任选地接合或稠合形成单环或多环的芳族或杂芳族环系;
L表示单键、具有5至60个碳原子的亚芳族环系或亚杂芳族环系中的一种或这些基团的组合;
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、Si(R0)3、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,所述基团中的每个可被一个或多个基团R0取代,其中一个或多个非相邻的-CH2-基团可被R0C=CR0、C≡C、Si(R0)2、Ge(R0)2、Sn(R0)2、C=O、C=S、C=Se、C=NR0、P(=O)(R0)、SO、SO2、NR0、O、S或CONR0代替,并且其中一个或多个氢原子可被氘原子、卤素原子或腈基代替,具有5至60个碳原子的芳族环或杂芳族环系、具有5至60个碳原子的芳胺基或杂芳胺基组成的组,其在每种情况下可以是相同的或不同的,其在每种情况下可以被一个或多个基团R0取代,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R0取代;
R0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个碳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,其中任意相邻的两个或多个相邻的R0可彼此形成单环或多环的脂族、芳族或杂芳族环系。
2.根据权利要求1所述的萘并芴衍生物,其特征在于,所述R1~R2在每次出现时相同或不同地选自由具有C1~C40的直链烷基、具有C3~C40的支链或环状的烷基、具有5至80个、优选5至60个碳原子的芳族环或杂芳族环系组成的群组,R1和R2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;
R3~R14在每次出现时相同或不同地选自由氢原子、氘原子、具有C1~C40的直链烷基、具有C3~C40的支链或环状的烷基、具有5至80个、优选5至60个碳原子的芳族环或杂芳族环系、或式(II)组成的群组,并且R13不是氢原子或氘原子;
Ar1、Ar2各自相同或者不同,选自由具有5至60个碳原子的芳族环系或杂芳族环系组成的群组,Ar1和Ar2可以任选地接合或稠合形成单环或多环的芳族或杂芳族环系;
L表示单键、具有5至60个碳原子的亚芳族环系或亚杂芳族环系中的一种或这些基团的组合;
6.一种有机电致发光材料,其特征在于,包括权利要求1-5任意一项所述的萘并芴衍生物。
7.一种有机电致发光元件,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至少一层有机层,其特征在于,所述有机层的至少一层包含权利要求1-5任意一项所述的萘并芴衍生物。
8.根据权利要求7所述的有机电致发光元件,其特征在于,所述的萘并芴衍生物在有机电致发光元件中用作空穴传输层材料、空穴注入层材料、激子阻挡层材料、荧光发光体或磷光发光体的基质材料。
9.一种消费型产品,其特征在于,包含权利要求7或8所述的有机电致发光元件。
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114014742A (zh) * | 2021-11-01 | 2022-02-08 | 上海八亿时空先进材料有限公司 | 一种三芳基苯衍生物、发光材料、发光元件及消费型产品 |
CN114907179A (zh) * | 2022-06-10 | 2022-08-16 | 上海八亿时空先进材料有限公司 | 蒽衍生物及使用其的有机电致发光材料、发光装置和消费型产品 |
WO2023065996A1 (zh) * | 2021-10-21 | 2023-04-27 | 上海八亿时空先进材料有限公司 | 蒽衍生物、有机电致发光材料、发光装置及消费型产品 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20180031385A (ko) * | 2016-09-20 | 2018-03-28 | 에스에프씨 주식회사 | 신규한 유기 화합물 및 이를 포함하는 유기 발광 소자 |
KR20190116691A (ko) * | 2018-04-05 | 2019-10-15 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 전자 소자 |
CN111448184A (zh) * | 2018-04-05 | 2020-07-24 | 株式会社Lg化学 | 化合物及包含其的有机电子器件 |
CN112979558A (zh) * | 2019-12-16 | 2021-06-18 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物、多种主体材料和包含其的有机电致发光装置 |
-
2021
- 2021-08-27 CN CN202110991724.7A patent/CN113429302B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20180031385A (ko) * | 2016-09-20 | 2018-03-28 | 에스에프씨 주식회사 | 신규한 유기 화합물 및 이를 포함하는 유기 발광 소자 |
KR20190116691A (ko) * | 2018-04-05 | 2019-10-15 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 전자 소자 |
CN111448184A (zh) * | 2018-04-05 | 2020-07-24 | 株式会社Lg化学 | 化合物及包含其的有机电子器件 |
CN112979558A (zh) * | 2019-12-16 | 2021-06-18 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物、多种主体材料和包含其的有机电致发光装置 |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023065996A1 (zh) * | 2021-10-21 | 2023-04-27 | 上海八亿时空先进材料有限公司 | 蒽衍生物、有机电致发光材料、发光装置及消费型产品 |
CN114014742A (zh) * | 2021-11-01 | 2022-02-08 | 上海八亿时空先进材料有限公司 | 一种三芳基苯衍生物、发光材料、发光元件及消费型产品 |
CN114014742B (zh) * | 2021-11-01 | 2024-05-10 | 上海八亿时空先进材料有限公司 | 一种三芳基苯衍生物、发光材料、发光元件及消费型产品 |
CN114907179A (zh) * | 2022-06-10 | 2022-08-16 | 上海八亿时空先进材料有限公司 | 蒽衍生物及使用其的有机电致发光材料、发光装置和消费型产品 |
CN114907179B (zh) * | 2022-06-10 | 2024-05-14 | 上海八亿时空先进材料有限公司 | 蒽衍生物及使用其的有机电致发光材料、发光装置和消费型产品 |
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