CN116675683A - 一种蒽并噁唑衍生物及其应用 - Google Patents
一种蒽并噁唑衍生物及其应用 Download PDFInfo
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- CN116675683A CN116675683A CN202310609896.2A CN202310609896A CN116675683A CN 116675683 A CN116675683 A CN 116675683A CN 202310609896 A CN202310609896 A CN 202310609896A CN 116675683 A CN116675683 A CN 116675683A
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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 title claims abstract description 15
- 239000000463 material Substances 0.000 claims abstract description 49
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- 239000010410 layer Substances 0.000 claims description 165
- -1 benzanthracenyl Chemical group 0.000 claims description 82
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 30
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 230000000903 blocking effect Effects 0.000 claims description 15
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- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 12
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Classifications
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Electroluminescent Light Sources (AREA)
Abstract
本发明属于有机电致发光材料技术领域,具体涉及一种蒽并噁唑衍生物及其应用。所述蒽并噁唑衍生物的结构通式如式(I)所示;将该蒽并噁唑衍生物作为载流子输送层的材料应用于有机电致发光元件时,由于蒽并噁唑衍生物的载流子迁移率比以往的材料大、具有优异的无定形性、并且薄膜状态稳定,因此,有机电致发光元件能够实现高效率、低驱动电压、长寿命。
Description
技术领域
本发明属于有机电致发光材料技术领域,具体涉及一种蒽并噁唑衍生物及其应用。
背景技术
有机电致发光二极管(OLED)又称为有机电致发光器件,是一种有机材料在电场作用下,通过载流子注入和复合导致发光的技术,它能够将电能通过有机发光材料转化成光能,包括无源驱动型OLED(PMOLED)和有源驱动型OLED(AMOLED)。OLED是继阴极射线管(CRT)、液晶显示器(LCD)之后的新一代显示技术,被称为梦幻般的显示技术。OLED在通信终端、军事领域和柔性显示方面也展现出了良好的发展前景。然而,与其他显示技术相比,OLED发展时间尚短,目前关于有机电致发光显示技术的理论体系仍不够全面系统,该领域也充满了机遇与挑战,例如器件效率差、制作要求与成本较高、器件寿命短与稳定性差等问题仍有待解决。
影响OLED器件效率的关键因素之一为器件中载流子的注入与复合过程,研究发现,通过平衡载流子,可以有效提高器件效率。然而,载流子的平衡很难控制,影响了发光层的激子复合发光,造成器件效率偏低。目前认为,OLED器件中空穴的传输速率远高于电子的传输速率,因此开发具有高传输速率的电子传输材料是提高器件发光效率的有效方式,具有重要的研究意义。一些常见的电子传输材料,如金属有机配合物,这类材料成膜性好、电子传输性能优良;喹啉类材料还原电势值低、机械性能良好且热稳定性高;三嗪类化合物具有优良的耐热性能和较高的电子亲和势能等优点;噁二唑类分子具有化学稳定性优良、电子传输速率高、可降低启动电压、热稳定性良好等优点。
噁唑与噁二唑结构相似,且均具有缺电子性能,但噁唑类的电子传输材料却不常见,噁唑结构在光电材料方面还未得到人们的重视。此前,研究发现可以通过对其进行功能化修饰,研究其作为电子传输材料的性能,填补噁唑作为电子传输材料的科研盲区,为今后的科研工作打下基础。
鉴于以上原因,特提出本发明。
发明内容
本发明的目的在于提供一种蒽并噁唑衍生物及其应用,该蒽并噁唑衍生物作为载流子输送层的材料应用于有机电致发光元件时,由于蒽并噁唑衍生物的载流子迁移率比以往的材料大、具有优异的无定形性、并且薄膜状态稳定,因此,有机电致发光元件能够实现高效率、低驱动电压、长寿命。
为了实现上述目的,本发明采用如下技术方案:
一种蒽并噁唑衍生物,所述蒽并噁唑衍生物的结构通式如式(I)所示:
其中,
R1~R6各自独立地选自由氢、氘、氰基、卤原子、取代或未取代的C1~C30烷基、取代或未取代的C3~C30环烷基、取代或未取代的C6~C50芳基、取代或未取代的C2~C50杂芳基、取代或未取代的C6~C50芳基胺基、取代或未取代的C1~C30烷基甲硅烷基、取代或未取代的C5~C50芳基甲硅烷基或*—(L)nNAr3Ar4组成的群组,任意相邻的两个或多个R1~R6可任意的接合或稠合形成取代或未取代的环,所形成的环中可任选地包含一个或多个额外的N、O、S、P、B、Si或Se杂原子;
L选自由单键、取代或未取代的C6~C50亚芳基、取代或未取代的C2~C50亚杂芳基组成的群组;
n表示0~5的整数;
Ar1、Ar2、Ar3、Ar4在每次出现时,各自独立地选自取代或未取代的C6~C50芳基、取代或未取代的C2~C50杂芳基、取代或未取代的C6~C50芳基胺基组成的群组;
*—表示R1~R6与式(I)的连接键。
进一步地,所述R1~R6各自独立地选自由氢、氘、氰基、取代或未取代的苯基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的四联苯基、取代或未取代的吡啶基、取代或未取代的嘧啶基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的三亚苯基、取代或未取代的蒽基、取代或未取代的苯并蒽基、取代或未取代的芘基、取代或未取代的基、取代或未取代的苝基、取代或未取代的荧蒽基、取代或未取代的咔唑基、取代或未取代的芴基、取代或未取代的吲哚基、取代或未取代的苯并呋喃基、取代或未取代的苯并噻吩基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩、取代或未取代的三嗪基、或*—(L)nNAr3Ar4组成的群组。
进一步地,所述Ar1、Ar2、Ar3、Ar4各自独立地选自由取代或未取代的苯基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的四联苯基、取代或未取代的吡啶基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的三亚苯基、取代或未取代的蒽基、取代或未取代的苯并蒽基、取代或未取代的芘基、取代或未取代的基、取代或未取代的苝基、取代或未取代的荧蒽基、取代或未取代的咔唑基、取代或未取代的芴基、取代或未取代的吲哚基、取代或未取代的苯并呋喃基、取代或未取代的苯并噻吩基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩组成的群组。
进一步地,所述R1~R6各自独立地选自由氢、氘、氰基、取代或未取代的苯基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的三亚苯基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基、或*—(L)mHet组成的群组;
Ar1、Ar2各自独立地选自由取代或未取代的苯基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的三亚苯基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基、或*—(L)mHet组成的群组;
m表示0~5的整数;
Het选自C2~C50杂芳基组成的群组;
*—表示R1~R6或Ar1、Ar2与式(I)的连接键。
本发明中使用的烷基是指碳原子数从1至40的直链或支链的饱和烃去除一个氢原子而得到的一价官能团。作为其非限制性例子,有甲基、乙基、丙基、异丁基、仲丁基、戊基、异戊基、己基等;
本发明意义上的芳基含有6~60个碳原子,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。此时,杂芳基的两个以上的环可以彼此简单附着或以缩合的形态附着,进一步地,也可以包含与芳基缩合的形态。作为芳基和杂芳基的非限制性例子,特别是选自以下所述基团:苯基、萘基、蒽基、苯并蒽基、菲基、芘基、基、苝基、荧蒽基、并四苯基、并五苯基、苯并芘基、联苯基、偶苯基、三联苯基、三聚苯基、四联苯基、芴基、螺二芴基、二氢菲基、三亚苯基、二氢芘基、四氢芘基、顺式或反式茚并芴基、顺式或反式茚并咔唑基、吲哚并咔唑基、苯并呋喃并咔唑基、苯并噻吩并咔唑基、苯并咔唑基、二苯并咔唑基、氮杂二苯并[g,Id]萘并[2,1,8-cde]薁、三聚茚基、异三聚茚基、螺三聚茚基、螺异三聚茚基、呋喃基、苯并呋喃基、异苯并呋喃基、二苯并呋喃基、噻吩基、苯并噻吩基、异苯并噻吩基、二苯并噻吩基、吡咯基、吲哚基、异吲哚基、咔唑基、吡啶基、喹啉基、异喹啉基、吖啶基、菲啶基、苯并[5,6]喹啉基、苯并[6,7]喹啉基、苯并[7,8]喹啉基、吩噻嗪基、吩噁嗪基、吡唑基、吲唑基、咪唑基、苯并咪唑基、萘并咪唑基、菲并咪唑基、吡啶并咪唑基、吡嗪并咪唑基、喹喔啉并咪唑基、噁唑基、苯并噁唑基、萘并噁唑基、蒽并噁唑基、菲并噁唑基、异噁唑基、1,2-噻唑基、1,3-噻唑基、苯并噻唑基、哒嗪基、六氮杂苯并菲基、苯并哒嗪基、嘧啶基、苯并嘧啶基、喹喔啉基、1,5-二氮杂蒽基、2,7-二氮杂芘基、2,3-二氮杂芘基、1,6-二氮杂芘基、1,8-二氮杂芘基、4,5-二氮杂芘基、4,5,9,10-四氮杂苝基、吡嗪基、吩嗪基、吩噁嗪基、吩噻嗪基、荧红环基、萘啶基、氮杂咔唑基、苯并咔啉基、咔啉基、菲咯啉基、1,2,3-三唑基、1,2,4-三唑基、苯并三唑基、1,2,3-噁二唑基、1,2,4-噁二唑基、1,2,5-噁二唑基、1,3,4-噁二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,2,5-噻二唑基、1,3,4-噻二唑基、1,3,5-三嗪基、1,2,4-三嗪基、1,2,3-三嗪基、四唑基、1,2,4,5-四嗪基、1,2,3,4-四嗪基、1,2,3,5-四嗪基、嘌呤基、蝶啶基、吲嗪基、喹唑啉基、苯并噻二唑基组成的群组或者衍生自这些体系的组合的基团。
本发明中使用的“卤素”或“卤原子”是指选自氟、氯、溴或碘。
本发明意义上的杂烷基是指烷基上的氢原子或-CH2-被至少一个杂原子取代,所述杂原子选自卤素、腈基、N、O、S或硅,作为非限制性的例子,有二氟甲基、三氟甲基、三氟乙基、五氟乙基、腈基、乙腈基、甲氧基甲基、甲氧基乙基、三甲基硅基、三异丙基硅基等。卤代烷基是指烷基上的氢原子被卤素部份取代或全取代,作为非限制性的例子,有氟甲苯、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、三氟乙基、五氟乙基等。
本发明使用的烯基或炔基至少含有两个碳原子,作为非限制性的例子,烯基或炔基优选被认为是指如下基团: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。
本发明使用的烷氧基、烷硫基优选具有1~40个碳原子的烷氧基或烷硫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、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、环烯基可以为环丙基、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N、O或S代替而形成杂环烷基、杂环烯基,例如,环戊基中的一个-CH2-基团被O代替形成四氢呋喃基、环己基中的一个-CH2-基团被O代替形成四氢吡喃基等;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。
本发明中使用的芳氧基是指R’O-所表示的一价官能团,上述R’是碳原子数从6至60的芳基。作为这样的芳氧基的非限制性例子,有苯氧基、萘氧基、联苯氧基等。
本发明中使用的芳硫基是指R”S-所表示的一价官能团,上述R”是碳原子数从6至60的芳基。作为这样的芳硫基的非限制性例子,有苯硫基、萘硫基、联苯硫基等。
本发明中使用的烷基硅基是指被碳原子数1至40的烷基取代的硅烷基,构成烷基硅基的碳原子数至少是3,作为烷基硅基的非限制性例子,有三甲基硅基、三乙基硅基等。芳基硅基是指被至少一个碳原子数从6至60的芳基取代的烷基硅基,作为非限制性例子,有苯基二甲基硅基、萘基二甲基硅基、苯基二乙基硅基、二苯基甲基硅基、二苯基乙基硅基,三苯基硅基等。
本发明意义上的“烷基羰基”、“烷氧基羰基”、“芳基羰基”、“芳基硼羰基”、“烷基硼羰基”是指被取代的羰基(-COR*),其中R*优选的选自由烷基、烷氧基、环烷基、芳基、杂芳基、芳基硼基、烷基硼基组成的群组。
本发明中使用的芳基磷基是指被碳原子数6至60的芳基取代的二芳基磷基,作为芳基磷基的非限制性例子,有二苯基磷基、二(4-三甲基硅基苯)磷基等。芳基氧磷基是二芳基磷基的磷原子被氧化至最高价态。
本发明中使用的芳基硼基是指被碳原子数6至60的芳基取代的二芳基硼基,作为芳基硼基的非限制性例子,有二苯基硼基、二(2,4,6-三甲基苯)硼基等。烷基硼基是指被碳原子数1至40的烷基取代的二烷基硼基,作为烷基硼基的非限制性例子,有二叔丁基硼基、二异丁基硼基等。
根据本发明的芳基烷基是指碳原子数从1至40的直链或支链的饱和烃的至少一个氢原子被碳原子数从6至60的芳基取代的烷基,作为非限制性的例子,可以为苯基甲基、二苯基甲基、三苯基甲基、2-苯基乙基、3-苯基丙基等。
根据本发明的烷基芳基是指碳原子数从6至60的芳基的至少一个氢原子被碳原子数从1至40的直链或支链的饱和烃取代的芳基,作为非限制性的例子,可以为甲基苯基、二甲基苯基、三甲基苯基、叔丁基苯基、异丙基苯基等。
作为优选地,所述杂芳基每次出现时,各自独立地选自由以下II-1~II-13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-C40烷基、C2-C40烯基、C2-C40炔基、C1-C40烷氧基、C3-C40环烷烃基、C3-C40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、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂芳基组成的群组;
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或NAr’;
Ar’选自由C1~C40的烷基、C1~C40的杂烷基、C3~C40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杂芳基组成的群组;优选地,Ar’为甲基、乙基、苯基、联苯基或萘基;
表示基团的连接位点。
进一步地,所述Het选自由式II-1~II-13所示基团组成的群组。
作为优选地,本发明“取代或未被取代的”这一用语是指,被选自氘、卤素、氰基、羧基、硝基、羟基、C1-C40烷基、C1-C40卤代烷基、C2-C40烯基、C2-C40炔基、C1-C40烷氧基、C1-C40烷硫基、C3-C40环烷基、C3-C40环烯基、3元至7元杂环烷基、C6-C60芳氧基、C6-C60芳硫基、未取代的或被一个或多个C6-C60芳基取代的3元至30元杂芳基、未取代的或被氘、一个或多个C1-C40烷基和一个或多个3元至30元杂芳基中的至少一个取代的C6-C60芳基、三(C1-C40)的烷基硅基、三(C6-C60)芳基硅基、二(C1-C40)的烷基(C6-C60)芳基硅基、C1-C40的烷基二(C6-C60)芳基硅基、C1-C40烷基羰基、C1-C40烷氧基羰基、C6-C60芳基羰基、二(C6-C60)的芳基硼羰基、二(C1-C40)烷基硼羰基、C1-C40烷基(C6-C60)芳基硼羰基、C6-C60芳基取代的(C1-C40)烷基、以及C1-C40烷基取代的(C6-C60)芳基中的1个以上的取代基取代或未被取代,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被取代。
本发明中的亚芳基是指碳原子数从6至60的芳烃去除两个氢原子而得到的二价官能团。作为其非限制性例子,有亚苯基、亚萘基、亚菲基、亚蒽基、亚芴基、亚螺二芴基等。
本发明中的亚杂芳基或杂亚芳基是指碳原子数从2至60的杂芳烃去除两个氢原子而得到的二价官能团。作为其非限制性例子,有亚吡啶基、亚喹啉基、亚异喹啉基、亚咔啉基、亚嘧啶基、亚三嗪基等。
根据前文所述的亚芳基、亚杂芳基作为二价官能团与Het或N连接,优选地,所述L每次出现时,各自独立地选自单键或由以下III-1~III-25所示基团组成的群组:
其中,X选自O、S、Se、CR’R”、SiR’R”或NAr’;
Z11、Z12、Z13、Z14每次出现时,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杂芳基组成的群组;
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;y5表示1或2的整数;
R’、R”每次出现时,各自独立地选自由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、联苯基或萘基;
其中,虚线代表基团的连接位点。
作为优选,所述X选自O或S。
作为优选,所述L各自独立地选自单键或由III-1~III-15、III-25所示基团组成的群组。
优选地,所述Z11、Z12、Z13、Z14各自独立地选自由氢、氘、氟、腈基组成的群组。
进一步的,所述的蒽并噁唑衍生物选自以下E100~E285结构中的一种或多种:
其中,*—G—*各自独立地选自*—O—*、*—S—*或下述所示结构中的一种:
*—和—*表示连接键。
如本文所使用,“其组合”或“群组”表示适用清单的一个或多个成员被组合以形成本领域普通技术人员能够从适用清单中设想的已知或化学稳定的布置。举例来说,烷基和氘原子可以组合形成部分或完全氘化的烷基;卤素和烷基可以组合形成卤代烷基取代基,例如三氟甲基等;并且卤素、烷基和芳基可以组合形成卤代芳烷基。
一种有机电致发光材料,所述的有机电致发光材料包括所述的蒽并噁唑衍生物。
有机电致发光材料可以单独使用本发明的蒽并噁唑衍生物构成,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蒽并噁唑衍生物可以用作但不限于发光层材料、载流子传输层材料、封盖层或电荷产生层材料。
一种有机电致发光装置,所述的有机电致发光装置包括第一电极、第二电极、封盖层和置于所述的第一电极和所述的第二电极之间的至少一层有机层,所述的有机层和封盖层中的至少一层包含本发明提供的蒽并噁唑衍生物。
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。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蒽并噁唑衍生物。
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。
在根据本发明的有机电致发光装置的其它层中,特别是在空穴传输层和封盖层中以及在电子传输层中,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,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,所述初压还可能更低,例如低于10-7Pa。
同样优选如下的有机电致发光器件,其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式I所示的稠环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稠环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装置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。
进一步的,所述有机层选自电子输送层、空穴阻挡层、电子阻挡层、空穴输送层、空穴注入层、发光层和电荷产生层中的一种或几种。
进一步的,所述电子输送层、发光层、封盖层或电荷产生层包含本发明的蒽并噁唑衍生物。
更进一步地,所述发光层包含本发明的蒽并噁唑衍生物。
进一步的,所述发光层包括掺杂物和发光主体,所述掺杂物包括由蒽、萘、蒽、芘、苝、菲、荧蒽、苯并蒽、芴、螺芴和并五苯及其衍生物或含有硼原子的化合物组成的群组,此外,还能够使用各种金属络合物、双苯乙烯基苯衍生物、噁唑衍生物、聚对亚苯基亚乙烯基衍生物、具有吲哚环作为稠环的部分结构的杂环化合物、具有咔唑环作为稠环的部分结构的杂环化合物、咔唑衍生物、噻唑衍生物、苯并咪唑衍生物、聚二烷基芴衍生物等。另外,作为掺杂剂材料,除此以外,还能够使用:在分子中具有芘骨架的芘衍生物、具有吲哚环作为稠环的部分结构的杂环化合物、具有咔唑环作为稠环的部分结构的杂环化合物、咔唑衍生物、噻唑衍生物、苯并咪唑衍生物、聚二烷基芴衍生物、喹吖啶酮、香豆素、红荧烯、苝及它们的衍生物、苯并吡喃衍生物、茚并菲衍生物、若丹明衍生物、氨基苯乙烯基衍生物等。它们可以单独成膜,也可以作为与其他材料一起混合而成膜的单层使用,也可以作为单独成膜的层之间、混合而成膜的层之间、或者单独成膜的层与混合而成膜的层的层叠结构。
另外,也可以使用磷光发光体作为掺杂物。作为磷光发光体,能够使用铱、铂等金属络合物的磷光发光体。可使用Ir(ppy)3等绿色磷光发光体、Firpic、Fir6等蓝色磷光发光体、Btp2Ir(acac)等红色磷光发光体等,作为此时的主体材料,优选使用本发明的咔唑衍生物。此外,作为空穴注入、传输性的主体材料(P型材料),能够使用4,4’-二(N-咔唑基)联苯(CBP)、4,4',4'-三(咔唑-9-基)三苯胺(TCTA)、9,9'-(1,3-苯基)二-9H-咔唑(mCP)等咔唑衍生物等。作为电子传输性的主体材料(n型材料),能够使用对-双(三苯基甲硅烷基)苯(UGH2)、2,2’,2”-(1,3,5-亚苯基)-三(1-苯基-1H-苯并咪唑)(TPBI)等,能够制作高性能的发光元件。
就磷光性的发光材料向主体材料的掺杂而言,为了避免浓度淬灭,优选在相对于发光层重量为1~10%的范围内通过共蒸镀进行掺杂。
另外,作为发光掺杂材料,也可以使用2-联苯基-4,6-双(12-苯基吲哚并[2,3-a]咔唑-11-基)-1,3,5-三嗪(PIC-TRZ)、9,9”-(6-苯基-1,3,5-三嗪-2,4-二基)双((9H-3,9'-联咔唑))(CC2TA)、苯并恶嗪-2,4,6-三苯基-1,3,5-三嗪(PXZ-TRZ)、2,4,5,6-四(9-咔唑基)-间苯二腈(4CzIPN)等发射延迟荧光的材料。
进一步的,所述发光主体包含本发明的蒽并噁唑衍生物。
进一步的,所述的掺杂物与发光主体的质量比为1:99~50:50。
一种由所述的有机电致发光装置制成的消费型产品,所述消费型产品包括本发明提供的有机电致发光装置。
本发明中所述的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:
本发明所述的蒽并噁唑衍生物具有大平面共轭的蒽并噁唑新型刚性结构,就本发明的通式(I)表示的化合物而言,由于具有(1)载流子的迁移率大;(2)内量子效率高;(3)薄膜状态稳定;(4)耐热性优异这样的特性,因此适合作为本发明的有机电致发光元件的发光层的构成材料来使用。
就将本发明的上述通式(I)表示的蒽并噁唑衍生物作为发光层的主体材料而使用本发明的有机电致发光元件而言,由于使用了载流子迁移率比以往的材料大、具有高的内量子效率、具有优异的无定形性、并且薄膜状态稳定的化合物,因此能够实现高效率、低驱动电压、长寿命的有机电致发光元件。
进而,在本发明中,通过上述通式(I)的蒽并噁唑衍生物来形成发光层,能够最大限度地有效利用该化合物具有的高量子效率性能和耐热性性,能够以更高效率实现长寿命的有机电致发光元件。
另外,在本发明中,就上述发光层、或两个以上的发光层配置的层叠膜的至少任一层中使用了由上述通式(I)表示的蒽并噁唑衍生物作为其构成材料的本发明的有机电致发光元件而言,由于使用了具有高载流子迁移率、高内量子效率和优异的无定形性、且薄膜状态稳定的化合物,因此能够实现高效率、低驱动电压、长寿命的有机电致发光元件。
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、空穴阻挡层107、电子传输层108、电子注入层109、阴极110以及封盖层(CPL)111。装置100可通过依序沉积所描述的层来制造。
图2展示两个发光层的有机发光装置200示意图。所述装置包含衬底201、阳极202、空穴注入203、空穴传输层204、第一发光层205、电子传输层206、电荷产生层207、空穴注入层208、空穴传输层209、第二发光层210、电子传输层211、电子注入层212以及阴极213。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装置具有一个发光层,而装置200具有第一发光层和第二发光层,第一发光层和第二发光层的发光峰形可以是重叠的或交叉重叠的或非重叠的。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提供如何从装置100的结构增加一些层的一个实例。
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。
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。
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。
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E155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,20.0mmol的3-氰基-2-碘萘溶于110mL的1,2-二氯乙烷中,再加入22.0mmol的NBS、10.0mmol的对甲苯磺酸和1.0mmol的醋酸钯,升温至70℃,搅拌反应12小时,降至室温,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,滤液减压浓缩干燥,用硅胶柱分离纯化,得到化合物Int-1,黄色固体,收率:83%。
第二步:化合物Int-2的制备
在氮气保护下,20.0mmol的Int-1溶于80mL干燥的THF中,降温至0℃,滴加入22.0mmol苯基溴化镁的THF溶液,搅拌反应1小时,升至室温,加入50mL的2M稀盐酸水溶液,分出有机相,水相用乙酸乙酯萃取,收集有机相干燥,过滤,滤液减压浓缩干燥,用硅胶柱分离纯化,得到化合物Int-2,黄色固体,收率:85%。
第三步:化合物Int-3的制备
在氮气保护下,20.0mmol的Int-2、22.0mmol的对氯苯甲酰胺基丙炔与60mL的乙腈和6mL的三乙胺混合,加入1.0mmol的碘化亚铜、1.0mmol的PdCl2(PPh3)2催化剂,升温至回流搅拌反应2小时,冷却到室温,加入100mL的饱和氯化铵水溶液,用乙酸乙酯萃取,收集有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到化合物Int-3,黄色固体,收率:65%。
第四步:化合物Int-4的制备
在氮气保护下,20.0mmol上步制备的Int-3、2.0mmol的三氟乙酸银、50mL的1,2-二氯乙烷和20.0mmol水混合,于室温搅拌反应2小时,再加入40.0mmol的对甲苯磺酸,升温至85℃搅拌反应1小时,冷却到室温,加入50mL的饱和碳酸氢钠水溶液,用乙酸乙酯萃取,收集有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到化合物Int-4,黄色固体,收率:62%。
第五步:化合物Int-5的制备
在氮气保护下,20.0mmol上步制备的Int-4、24.0mmol的苯硼酸、60.0mmol的无水碳酸钠、2.0mmol的四丁基溴化铵、0.1mmol的Pd(PPh3)4和60mL的甲苯溶液混合,再加入30mL的乙醇和30mL的水,升温至回流搅拌反应15小时,降至室温,加入50mL水,分出有机相,水相用甲苯萃取,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Int-5,收率73%。
第六步:化合物Int-6的制备
在氮气保护下,20.0mmol上步制备的Int-5和2.0mmol的对甲苯磺酸溶于100mL的二氯甲烷,分批加入22.0mmol的NBS,搅拌反应2小时,加入50mL水,分出有机相,水相用二氯甲烷萃取,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Int-6,收率93%。
第七步:化合物Int-7的制备
参照第五步的合成方法,仅将Int-4替换为Int-6,制备获得到化合物Int-7,收率84%。
第八步:化合物Int-8的制备
在氮气保护下,20.0mmol上步制备的Int-7、24.0mmol的联硼酸频哪醇酯、30.0mmol的无水醋酸钾、2.0mmol的碘化亚铜、0.2mmol的PdCl2(dppf)、0.4mmol的XPhos和80mL的DMF混合,升温至100℃,搅拌反应15小时,降至室温,将反应液倒入150mL饱和的氯化钠水溶液,过滤,滤饼用水洗,用硅胶柱分离纯化,得到化合物Int-8,白色固体,收率85%。
第九步:化合物E950的制备
在氮气保护下,22.0mmol上步制备的Int-8(反应物1)、20.0mmol的对溴苯腈(反应物2)、60.0mmol的无水碳酸钠、2.0mmol的四丁基溴化铵、0.1mmol的Pd(PPh3)4和60mL的甲苯溶液混合,再加入30mL的乙醇和30mL的水,升温至回流搅拌反应15小时,降至室温,加入50mL水,分出有机相,水相用甲苯萃取,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E155,收率76%,MS(TOF):m/z 625.2218[M+H]+,1HNMR(δ、CDCl3):8.22(2H,s);7.94~7.92(2H,d);7.84~7.80(5H,m);7.65~7.58(4H,m);7.54~7.46(6H,m);7.44~7.36(5H,m);7.26~7.24(2H,d);7.22~7.20(2H,d)。
实施例2~实施例102
参照上述类似的合成方法,制备以下化合物:
实施例103化合物E238的制备:
在氮气保护下,22.0mmol的Int-4’(反应物1)、20.0mmol的二([1,1'-联苯基]-4-基)胺(反应物2)、30.0mmol的叔丁醇钠与60mL的甲苯混合,再加入0.2mmol的Pd2(dba)3催化剂和0.4mmol的Xantphos,升温至110℃搅拌反应15小时,冷却到室温,加入50mL的水,用乙酸乙酯萃取,收集有机相干燥,过滤,滤液减压浓缩干燥,用硅胶柱分离纯化,得到化合物E238,黄色固体,收率86%,MS(TOF):m/z691.2763[M+H]+,1HNMR(δ、CDCl3):8.51~8.49(2H,d);8.16~8.14(2H,m);7.82(1H,s);7.75~7.69(4H,m);7.66~7.60(4H,m);7.57~7.45(12H,m);7.42~7.36(4H,m);7.34~7.29(4H,m);7.15~7.11(1H,m)。
实施例104~实施例187
参照上述实施例类似的合成方法,制备以下化合物:
上述实施例中,*—G—*各自独立地选自*—O—*、*—S—*或下述所示结构中的一种:
*—和—*表示连接键。
应用例1~应用例186
一种OLED元件100,如图1所示,本实施例的OLED元件为顶发射光元件,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上的有机发光层106、设于有机发光层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以及设于电子注入层109上的阴极110和阴极之上的封盖层111,不包含空穴阻挡层107的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,抽真空至小于1×10-5Pa,在上述ITO膜上蒸镀金属银作为阳极层,蒸镀膜厚为继续分别蒸镀化合物HI01和HI02作为空穴注入层,其中,HI02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化合物HT025作为电子阻挡层,蒸镀膜厚为
5)在电子阻挡层上继续蒸镀本发明的式(I)所示化合物作为主体材料以及RD030为掺杂材料,其中,RD030为式(I)所示化合物质量的5%,作为元件的有机发光层,蒸镀所得有机发光层的膜厚为
6)在有机发光层上继续蒸镀一层LiQ和化合物ET036作为元件的电子传输层,其中,化合物ET036为LiQ质量的40%,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元件的透明阴极层,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HTM作为元件的CPL层,蒸镀膜厚为得到本发明提供的OLED元件。
上述应用例中使用的化合物结构如下:
应用例187
一种有机电致发光元件200,其结构如图2所示,其包含衬底201、阳极202、空穴注入203、空穴传输层204、第一发光层205、电子传输层206、电荷产生层207、空穴注入层208、空穴传输层209、第二发光层210、电子传输层211、电子注入层212以及阴极213,参照实施例6类似的制备方法制备电致发光元件200。
对比例1
按照与应用例1相同的步骤,将步骤5)中的本发明的(I)所示化合物式替换为E02,得到对比元件1;
在同样亮度下,使用数字源表及亮度计测定应用例1~应用例186、应用例187及对比例1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亮度达到1000cd/m2时的电压即驱动电压,同时测出此时的电流密度;亮度与电流密度的比值即为电流效率;LT90%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900cd/m2的时间,单位为小时。所有结果概述于表1中,以对比例1的测试数据(括号内数据)为基准归一化以便于比较。
表1各元件性能检测结果
其中,Me为甲基;Ph为苯基;PhPh为联苯基,Nap为萘基。
本发明的化合物作为发光层的材料获得了高效率和长寿命的有机电致发光元件,元件的驱动电压低、电流效率高,LT90%寿命也取得优异的表现,表明本发明的化合物是性能优异的有机电致发光材料。
对比例1中的化合物E02与本发明的化合物相比,区别在于E02的菲并噁唑引入三芳基胺基团后,电子传输能力比空穴传输能力弱,造成元件内激子的传送不平衡,元件驱动电压升高,效率降低。而本发明的化合物在蒽并噁唑母核引入取代基团后增强了平面共轭,提高了电子传输能力,所以其激子的传输性能有较大幅度的提升,元件内激子的传输更加平衡,元件性能提高显著。
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。
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 (10)
1.一种蒽并噁唑衍生物,其特征在于,所述蒽并噁唑衍生物的结构通式如式(I)所示:
其中,
R1~R6各自独立地选自由氢、氘、氰基、卤原子、取代或未取代的C1~C30烷基、取代或未取代的C3~C30环烷基、取代或未取代的C6~C50芳基、取代或未取代的C2~C50杂芳基、取代或未取代的C6~C50芳基胺基、取代或未取代的C1~C30烷基甲硅烷基、取代或未取代的C5~C50芳基甲硅烷基或*—(L)nNAr3Ar4组成的群组,任意相邻的两个或多个R1~R6可任意的接合或稠合形成取代或未取代的环,所形成的环中可任选地包含一个或多个额外的N、O、S、P、B、Si或Se杂原子;
L选自由单键、取代或未取代的C6~C50亚芳基、取代或未取代的C2~C50亚杂芳基组成的群组;
n表示0~5的整数;
Ar1、Ar2、Ar3、Ar4在每次出现时,各自独立地选自取代或未取代的C6~C50芳基、取代或未取代的C2~C50杂芳基、取代或未取代的C6~C50芳基胺基组成的群组;
*—表示R1~R6与式(I)的连接键。
2.根据权利要求1所述的蒽并噁唑衍生物,其特征在于,所述R1~R6各自独立地选自由氢、氘、氰基、取代或未取代的苯基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的四联苯基、取代或未取代的吡啶基、取代或未取代的嘧啶基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的三亚苯基、取代或未取代的蒽基、取代或未取代的苯并蒽基、取代或未取代的芘基、取代或未取代的基、取代或未取代的苝基、取代或未取代的荧蒽基、取代或未取代的咔唑基、取代或未取代的芴基、取代或未取代的吲哚基、取代或未取代的苯并呋喃基、取代或未取代的苯并噻吩基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩、取代或未取代的三嗪基、或*—(L)nNAr3Ar4组成的群组;
和/或,所述Ar1、Ar2、Ar3、Ar4各自独立地选自由取代或未取代的苯基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的四联苯基、取代或未取代的吡啶基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的三亚苯基、取代或未取代的蒽基、取代或未取代的苯并蒽基、取代或未取代的芘基、取代或未取代的基、取代或未取代的苝基、取代或未取代的荧蒽基、取代或未取代的咔唑基、取代或未取代的芴基、取代或未取代的吲哚基、取代或未取代的苯并呋喃基、取代或未取代的苯并噻吩基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩组成的群组。
3.根据权利要求1所述的蒽并噁唑衍生物,其特征在于,所述R1~R6各自独立地选自由氢、氘、氰基、取代或未取代的苯基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的三亚苯基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基、或*—(L)mHet组成的群组;
所述Ar1、Ar2各自独立地选自由取代或未取代的苯基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的三亚苯基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基、或*—(L)mHet组成的群组;
m表示0~5的整数;
Het选自C2~C50杂芳基组成的群组;
*—表示R1~R6或Ar1、Ar2与式(I)的连接键。
4.根据权利要求1~3任一项所述的蒽并噁唑衍生物,其特征在于,所述杂芳基每次出现时,各自独立地选自由以下II-1~II-13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-C40烷基、C2-C40烯基、C2-C40炔基、C1-C40烷氧基、C3-C40环烷烃基、C3-C40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、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂芳基组成的群组;
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或NAr’;
Ar’选自由C1~C40的烷基、C1~C40的杂烷基、C3~C40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杂芳基组成的群组;优选地,Ar’为甲基、乙基、苯基、联苯基或萘基;
表示基团的连接位点。
5.根据权利要求1~3任一项所述的蒽并噁唑衍生物,其特征在于,所述L每次出现时,各自独立地选自单键或由以下III-1~III-25所示基团组成的群组:
其中,X选自O、S、Se、CR’R”、SiR’R”或NAr’;
Z11、Z12、Z13、Z14每次出现时,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杂芳基组成的群组;
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;y5表示1或2的整数;
R’、R”每次出现时,各自独立地选自由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、联苯基或萘基;
其中,虚线代表基团的连接位点。
6.根据权利要求1-5任意一项所述的蒽并噁唑衍生物,其特征在于,所述蒽并噁唑衍生物选自以下所示E100~E285结构中的一种或多种:
其中,*—G—*各自独立地选自*—O—*、*—S—*或下述所示结构中的一种:
*—和—*表示连接键。
7.一种有机电致发光材料,其特征在于,所述的有机电致发光材料包括权利要求1-6任意一项所述的蒽并噁唑衍生物。
8.一种有机电致发光装置,其特征在于,所述的有机电致发光装置包括第一电极、第二电极、封盖层和置于所述的第一电极和所述的第二电极之间的至少一层有机层,所述有机层和封盖层中的至少一层包含权利要求1-6任意一项所述的蒽并噁唑衍生物。
9.根据权利要求8所述的有机电致发光装置,其特征在于,所述有机层包括空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层或电荷产生层;其中任一有机层可以是一层、二层或多层;
优选地,所述的发光层、电子传输层、封盖层和电荷产生层中的至少一层中包含权利要求1-6任意一项所述的蒽并噁唑衍生物。
10.一种消费型产品,其特征在于,包含权利要求8或9所述的有机电致发光装置。
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