CN113816861A - 芳香胺化合物、混合物、组合物及有机电子器件 - Google Patents
芳香胺化合物、混合物、组合物及有机电子器件 Download PDFInfo
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- CN113816861A CN113816861A CN202110056673.9A CN202110056673A CN113816861A CN 113816861 A CN113816861 A CN 113816861A CN 202110056673 A CN202110056673 A CN 202110056673A CN 113816861 A CN113816861 A CN 113816861A
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- 125000003118 aryl group Chemical group 0.000 claims description 34
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
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- 229910052717 sulfur Inorganic materials 0.000 claims description 5
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- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
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- 238000000504 luminescence detection Methods 0.000 description 1
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- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
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- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
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- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
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- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
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- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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Abstract
本发明涉及一种芳香胺化合物、混合物、组合物及有机电子器件。该芳香胺化合物具有式(1)所示结构,表现出优异的空穴传输性质及稳定性,可作为有机电致发光器件中的空穴传输层材料既可降低驱动电压,也可提高电致发光效率,以及延长器件的寿命。
Description
本申请要求于2020年6月19日提交中国专利局、申请号为2020105676514、发明名称为“一种芳香胺化合物及其在有机电子器件中的应用”的中国专利申请的优先权,其全部内容通过引用结合在本申请中。
技术领域
本发明涉及有机电致发光技术领域,特别是涉及一种芳香胺化合物、混合物、组合物及有机电子器件。
背景技术
由于有机发光二极管(OLED)具有种类多、制造成本低和光学与电学性能良好等优点,其在光电器件(例如平板显示器和照明)的应用方面具有很大的潜力。
有机电致发光现象是指利用有机物质将电能转化为光能的现象。利用有机电致发光现象的有机电致发光元件通常具有正极与负极以及在它们中间包含有机物层的结构。为了提高有机电致发光元件的效率与寿命,有机物层具有多层结构,每一层包含有不同的有机物质。具体的,可以包括空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等。在这种有机电致发光元件中,在两个电极之间施加电压,则由正极向有机物层注入空穴,由负极向有机物层注入电子,当注入的空穴与电子相遇时形成激子,该激子跃迁回基态时发出光。这种有机电致发光元件具有自发光、高亮度、高效率、低驱动电压、广视角、高对比度、高响应性等特性。
然而OLED器件在发光效率及使用寿命还需要进一步改善,因为OLED作为电流驱动器件,工作时处于高电流密度状态,材料容易出现焦耳热,导致器件劣化,尤其是在阳极和空穴传输层之间。常用的空穴传输材料玻璃化转变温度较低,焦耳热的积累导致薄膜形貌发生变化,同时会加速材料分解,从而影响器件寿命。此外,有机半导体材料的空穴迁移率普遍高于电子迁移率,导致的空穴-电子传输不平衡从而影响器件发光效率。
目前虽然有大量的空穴传输材料已被开发出来,但仍然存在很多问题,如何设计新的性能更好的材料进行调节,从而达到降低器件电压,提高器件效率和寿命的效果,一直是本领域技术人员亟待解决的问题。
发明内容
基于此,本发明的目的在于提供一种芳香胺化合物、混合物、组合物及有机电子器件,提高器件的效率和寿命。
技术方案如下:
一种芳香胺化合物,具有如通式(1)所示的结构:
其中:
L1-L6独立选自单键,或取代或未取代环原子数为6至40的芳香基团或杂芳香基团;
Ar1-Ar4独立选自取代或未取代环原子数为6至40的芳香基团,或取代或未取代环原子数为5至40的杂芳香基团或非芳香环系。
本发明还提供一种高聚物,所述高聚物包含至少一个重复单元,所述重复单元包含上述的式(1)所示的结构单元。
本发明还提供一种混合物,所述混合物包括上述的芳香胺化合物或上述的高聚物,及至少另一种有机功能材料,所述另一种有机功能材料选自空穴注入材料、空穴传输材料、电子传输材料、电子注入材料、电子阻挡材料、空穴阻挡材料、发光材料、主体材料和有机染料中的至少一种。
本发明还提供一种组合物,所述组合物包括上述的芳香胺化合物或上述的高聚物或上述的混合物,及至少一种有机溶剂。
本发明还提供一种有机电子器件,其至少包括上述的芳香胺化合物,或上述的高聚物,或上述的混合物,或由上述的组合物制备而成。
与现有技术相比,本发明具有如下有益效果:
本发明提供的芳香胺化合物,具有优异的空穴传输性质及稳定性,可作为有机电致发光器件中的空穴传输层材料这样既可降低驱动电压,也可提高电致发光效率,以及延长器件的寿命。
具体实施方式
以下结合具体实施例对本发明作进一步详细的说明。本发明可以以许多不同的形式来实现,并不限于本文所描述的实施方式。相反地,提供这些实施方式的目的是使对本发明公开内容理解更加透彻全面。
除非另有定义,本文所使用的所有的技术和科学术语与属于本发明的技术领域的技术人员通常理解的含义相同。本文中在本发明的说明书中所使用的术语只是为了描述具体的实施例的目的,不是旨在于限制本发明。本文所使用的术语“和/或”包括一个或多个相关的所列项目的任意的和所有的组合。
在本发明中,“取代”表示被取代基中的氢原子被取代基所取代。
本发明中,“取代或未取代”表示所定义的基团可以被取代,也可以不被取代。当所定义的基团被取代时,应理解为任选被本领域可接受的基团所取代,包括但不限于:C1-30烷基、含有3至20个环原子的环烷基、含有3至20个环原子的杂环基、含有5至20个环原子的芳基、含有5至20个环原子的杂芳基、硅烷基、羰基、烷氧基羰基、芳氧基羰基、氨基甲酰基、卤甲酰基、甲酰基、-NRR′、氰基、异氰基、异氰酸酯基、硫氰酸酯基、异硫氰酸酯基、羟基、三氟甲基、硝基或卤素,且上述基团也可以进一步被本领域可接受取代基取代;可理解的,-NRR′中的R和R′各自独立地为本领域可接受的基团所取代,包括但不限于H、C1-6烷基、含有3至8个环原子的环烷基、含有3至8个环原子的杂环基、含有5至20个环原子的芳基或含有5至10个环原子的杂芳基;所述C1-6烷基、含有3至8个环原子的环烷基、含有3至8个环原子的杂环基、含有5至20个环原子的芳基或含有5至10个环原子的杂芳基任选进一步被一个或多个以下基团取代:C1-6烷基、含有3至8个环原子的环烷基、含有3至8个环原子的杂环基、卤素、羟基、硝基或氨基。
在本发明中,“环原子数”表示原子键合成环状而得到的结构化合物(例如,单环化合物、稠环化合物、交联化合物、碳环化合物、杂环化合物)的构成该环自身的原子之中的原子数。该环被取代基所取代时,取代基所包含的原子不包括在成环原子内。关于以下所述的“环原子数”,在没有特别说明的条件下也是同样的。例如,苯环的环原子数为6,萘环的环原子数为10,噻吩基的环原子数为5。
“芳基或芳香基团”是指在芳香环化合物的基础上除去一个氢原子衍生的芳族烃基,可以为单环芳基、或稠环芳基、或多环芳基,对于多环的环种,至少一个是芳族环系。例如,“取代或未取代的具有6至40个环原子的芳基”是指包含6至40个环原子的芳基,优选取代或未取代的具有6至30个环原子的芳基,更优选取代或未取代的具有6至18个环原子的芳基,特别优选取代或未取代的具有6至14个环原子的芳基,且芳基上任选进一步被取代;合适的实例包括但不限于:苯、联苯、三联苯、萘、蒽、荧蒽、菲、苯并菲、二萘嵌苯、并四苯、芘、苯并芘、苊、芴及其衍生物。可以理解地,多个芳基也可以被短的非芳族单元间断(例如<10%的非H原子,比如C、N或O原子),具体如苊、芴,或者9,9-二芳基芴、三芳胺、二芳基醚体系也应该包含在芳基的定义中。
“杂芳基或杂芳香基团”是指在芳基的基础上至少一个碳原子被非碳原子所替代,非碳原子可以为N原子、O原子、S原子等。例如,“取代或未取代的具有5至40个环原子的杂芳基”是指具有5至40个环原子的杂芳基,,优选取代或未取代的具有6至30个环原子的杂芳基,更优选取代或未取代的具有6至18个环原子的杂芳基,特别优选取代或未取代的具有6至14个环原子的杂芳基,且杂芳基任选进一步被取代,合适的实例包括但不限于:三嗪、吡啶、嘧啶、咪唑、呋喃、噻吩、苯并呋喃、苯并噻吩、吲哚、咔唑、吡咯并咪唑、吡咯并吡咯、噻吩并吡咯、噻吩并噻吩、呋喃并吡咯、呋喃并呋喃、噻吩并呋喃、苯并异噁唑、苯并异噻唑、苯并咪唑、喹啉、异喹啉、邻二氮萘、喹喔啉、菲啶、伯啶、喹唑啉、喹唑啉酮、二苯并噻吩、二苯并呋喃、咔唑及其衍生物。
“胺基”是指氨的衍生物,具有式-N(X)2的结构特征,其中每个“X”独立地是H、取代的或未被取代的烷基、取代的或未被取代的环烷基、取代的或未被取代的杂环基等。胺基的非限制性类型包括-NH2、-N(烷基)2、-NH(烷基)、-N(环烷基)2、-NH(环烷基)、-N(杂环基)2、-NH(杂环基)、-N(芳基)2、-NH(芳基)、-N(烷基)(芳基)、-N(烷基)(杂环基)、-N(环烷基)(杂环基)、-N(芳基)(杂芳基)、-N(烷基)(杂芳基)等。
“卤素”或“卤基”是指F、Cl、Br或I。
“烷基氨基”是指被至少一个烷基取代的氨基。合适的实例包括但不限于:-NH2、-NH(CH3)、-N(CH3)2、-NH(CH2CH3)、-N(CH2CH3)2。
“芳基烷基”是指烷基上至少一个键合至碳原子的氢原子被芳基代替衍生形成的烃基。其中芳基部分可以包括5~20个碳原子,烷基部分可以包括1~9个碳原子。合适的实例包括但不限于:苄基、2-苯基乙-1-基、萘基甲基、2-萘基乙-1-基、萘并苄基和2-萘并苯基乙-1-基。
术语“烷氧基”是指具有-O-烷基的基团,即如上所定义的烷基经由氧原子连接至母核结构。包含该术语的短语,合适的实例包括但不限于:甲氧基(-O-CH3或-OMe)、乙氧基(-O-CH2CH3或-OEt)和叔丁氧基(-O-C(CH3)3或-OtBu)。
本发明中,与单键相连的“*”表示连接位点。
在本发明实施例中,有机材料的能级结构,三线态能级ET、HOMO、LUMO起着关键的作用。下面对这些能级的做介绍。
HOMO和LUMO能级可以通过光电效应进行测量,例如XPS(X射线光电子光谱法)和UPS(紫外光电子能谱)或通过循环伏安法(以下简称CV)。最近,量子化学方法,例如密度泛函理论(以下简称DFT),也成为行之有效的计算分子轨道能级的方法。
有机材料的三线态能级ET1可通过低温时间分辨发光光谱来测量,或通过量子模拟计算(如通过Time-dependent DFT)得到,如通过商业软件Gaussian 09W(Gaussian Inc.),具体的模拟方法可参见WO2011141110或如下在实施例中所述。
应该注意,HOMO、LUMO、ET1的绝对值取决于所用的测量方法或计算方法,甚至对于相同的方法,不同评价的方法,例如在CV曲线上起始点和峰点可给出不同的HOMO/LUMO值。因此,合理有意义的比较应该用相同的测量方法和相同的评价方法进行。本发明实施例的描述中,HOMO、LUMO、ET1的值是基于Time-dependent DFT的模拟,但不影响其他测量或计算方法的应用。
在发明中,(HOMO-1)定义为第二高的占有轨道能级,(HOMO-2)为第三高的占有轨道能级,以此类推。(LUMO+1)定义为第二低的未占有轨道能级,(LUMO+2)为第三低的占有轨道能级,以此类推。
本发明的目的在于提供一种含氧化噻吩的稠环化合物及其应用,提高器件的效率和寿命。
技术方案如下:
一种芳香胺化合物,具有如通式(1)所示的结构:
其中:
L1-L6独立选自单键,或取代或未取代环原子数为6至40的芳香基团或杂芳香基团;
Ar1-Ar4独立选自取代或未取代环原子数为6至40的芳香基团,或取代或未取代环原子数为5至40的杂芳香基团或非芳香环系。
在一实施例中,,L5-L6选自单键、苯、萘、蒽、菲、芘、吡啶、嘧啶、三嗪、芴、硫芴、硅芴、咔唑、噻吩、呋喃、噻唑、三苯胺、三苯基氧磷,四苯基硅、螺芴、螺硅芴等基团。
进一步地,L5-L6选自单键或具有苯、萘、吡啶、嘧啶或三嗪结构。
在一实施例中,L5-L6选自相同的基团;进一步,L5-L6同时选自单键或苯基。
进一步地,L5-L6选自单键,所述的芳香胺化合物如通式(2)所示:
在一实施例中,通式(1)或通式(2)中Ar1和Ar3选自相同的结构;进一步,通式(1)或通式(2)中*-L1-Ar1与*-L3-Ar3选自相同的结构。
在一实施例中,通式(1)或通式(2)中Ar1和Ar3选自相同的结构,且Ar2和Ar4选自相同的结构。
在一实施例中,通式(1)或通式(2)中*-L1-Ar1与*-L3-Ar3选自相同的结构;进一步地,*-L2-Ar2与*-L4-Ar4选自相同的结构。
需要说明的是,在本发明中,*-L1-Ar1与*-L3-Ar3不成环;*-L3-Ar2与*-L4-Ar4不成环。
在一实施例中,所述的Ar1-Ar4独立选自以下所示结构中的任意一种:
其中:
X选自N或CR1;
Y选自O、S、S=O、SO2、NR2、PR2、CR2R3或SiR2R3;
R1-R3每次出现时,分别独立选自:氢,D,具有1至20个C原子的直链烷基,具有1至20个C原子的直链烷氧基,具有1至20个C原子的直链硫代烷氧基,具有3至20个C原子的支链烷基或环状的烷基,具有3至20个C原子的支链烷氧基或环状的烷氧基,具有3至20个C原子的支链硫代烷氧基或环状的硫代烷氧基,甲硅烷基,具有1至20个C原子的酮基,具有2至20个C原子的烷氧基羰基,具有7至20个C原子的芳氧基羰基,氰基,氨基甲酰基,卤甲酰基、甲酰基,异氰基,异氰酸酯基,硫氰酸酯基,异硫氰酸酯基,羟基,硝基,CF3,Cl,Br,F,可交联的基团,具有6至20个环原子的取代或未取代的芳香基团,具有5至20个环原子的取代或未取代的杂芳香基团,具有5至20个环原子的芳氧基,具有5至20个环原子的杂芳氧基基团,或这些基团的组合。
进一步,R1-R3每次出现时,分别独立选自:氢,D,具有1至10个C原子的直链烷基,具有3至10个C原子的支链烷基或环状的烷基,或苯基。
进一步地,通式(1)中的Ar1-Ar4分别独立地选自以下基团中的一种:
n选自0,1,2,3或4。
进一步地,通式(1)中的Ar1-Ar4分别独立选自以下基团中的任意一种:
在一实施例中,通式(1)选自如下所示的结构:
在一实施例中,L1-L4独立选自单键,或取代或未取代环原子数为6至20的芳香基团或杂芳香基团;进一步,L1-L4独立选自单键,或环原子数为6至12的芳香基团;
进一步地,L1-L4每次出现时,分别独立选自单键或以下基团:
在一实施例中,L1-L4每次出现时,分别独立选自单键或苯基。
在一实施例中,通式(1)选自通式(3-1)-(3-6)任一结构:
进一步地,通式(3-1)-(3-6)中L1-L4分别独立选自单键或苯基。
在一实施例中,通式(3-1)-(3-6)中L2、L4选自苯基。更进一步,L1、L3选自单键或苯基。
在一实施例中,通式(3-1)或(3-5)中Y选自O或S。
在一实施例中,L1-L6独立选自单键或苯基。
下面列出本发明的芳香胺化合物的例子,但不限于:
按照本发明的芳香胺化合物,可以作为功能材料用于电子器件的有机功能层中。有机功能层包括,但不限于,空穴注入层(HIL),空穴传输层(HTL),电子传输层(ETL),电子注入层(EIL),电子阻挡层(EBL),空穴阻挡层(HBL),发光层(EML)。
在一实施例中,按照本发明的芳香胺化合物用于空穴传输层中。
本发明进一步涉及一种混合物,包含有至少一种以上所述的芳香胺化合物,及至少另一种有机功能材料,所述至少另一种的有机功能材料可选于空穴注入材料(HIM),空穴传输材料(HTM),电子传输材料(ETM),电子注入材料(EIM),电子阻挡材料(EBM),空穴阻挡材料(HBM),发光材料(Emitter),主体材料(Host)和有机染料。例如在WO2010135519A1,US20090134784A1和WO2011110277A1中对各种有机功能材料有详细的描述,特此将此3专利文件中的全部内容并入本文作为参考。
在一实施例中,所述另一种有机功能材料选自电子传输材料,作为共主体运用于电子器件中。
本发明还涉及一种组合物,包含至少一种如上所述的芳香胺化合物或混合物,及至少一种有机溶剂;所述的至少一种的有机溶剂选自芳族或杂芳族、酯、芳族酮或芳族醚、脂肪族酮或脂肪族醚、脂环族或烯烃类化合物,或硼酸酯或磷酸酯类化合物,或两种及两种以上溶剂的混合物。
在一个优选的实施例中,按照本发明的一种组合物,其特征在于,所述的至少的一种有机溶剂选自基于芳族或杂芳族的溶剂。
适合本发明的基于芳族或杂芳族溶剂的例子有,但不限制于:对二异丙基苯、戊苯、四氢萘、环己基苯、氯萘、1,4-二甲基萘、3-异丙基联苯、对甲基异丙苯、二戊苯、三戊苯、戊基甲苯、邻二乙苯、间二乙苯、对二乙苯、1,2,3,4-四甲苯、1,2,3,5-四甲苯、1,2,4,5-四甲苯、丁苯、十二烷基苯、二己基苯、二丁基苯、对二异丙基苯、环己基苯、苄基丁基苯、二甲基萘、3-异丙基联苯、对甲基异丙苯、1-甲基萘、1,2,4-三氯苯、4,4-二氟二苯甲烷、1,2-二甲氧基-4-(1-丙烯基)苯、二苯甲烷、2-苯基吡啶、3-苯基吡啶、N-甲基二苯胺、4-异丙基联苯、α,α-二氯二苯甲烷、4-(3-苯基丙基)吡啶、苯甲酸苄酯、1,1-双(3,4-二甲基苯基)乙烷、2-异丙基萘、喹啉、异喹啉、2-呋喃甲酸甲酯、2-呋喃甲酸乙酯等;
适合本发明的基于芳族酮溶剂的例子有,但不限制于:1-四氢萘酮,2-四氢萘酮,2-(苯基环氧)四氢萘酮,6-(甲氧基)四氢萘酮,苯乙酮、苯丙酮、二苯甲酮、及它们的衍生物,如4-甲基苯乙酮、3-甲基苯乙酮、2-甲基苯乙酮、4-甲基苯丙酮、3-甲基苯丙酮、2-甲基苯丙酮等;
适合本发明的基于芳族醚溶剂的例子有,但不限制于:3-苯氧基甲苯、丁氧基苯、对茴香醛二甲基乙缩醛、四氢-2-苯氧基-2H-吡喃、1,2-二甲氧基-4-(1-丙烯基)苯、1,4-苯并二噁烷、1,3-二丙基苯、2,5-二甲氧基甲苯、4-乙基本乙醚、1,3-二丙氧基苯、1,2,4-三甲氧基苯、4-(1-丙烯基)-1,2-二甲氧基苯、1,3-二甲氧基苯、缩水甘油基苯基醚、二苄基醚、4-叔丁基茴香醚、反式-对丙烯基茴香醚、1,2-二甲氧基苯、1-甲氧基萘、二苯醚、2-苯氧基甲醚、2-苯氧基四氢呋喃、乙基-2-萘基醚;
在一些优选的实施例中,按照本发明的组合物,所述的至少一种的有溶剂可选自:脂肪族酮,例如,2-壬酮、3-壬酮、5-壬酮、2-癸酮、2,5-己二酮、2,6,8-三甲基-4-壬酮、葑酮、佛尔酮、异佛尔酮、二正戊基酮等;或脂肪族醚,例如,戊醚、己醚、二辛醚、乙二醇二丁醚、二乙二醇二乙醚、二乙二醇丁基甲醚、二乙二醇二丁醚、三乙二醇二甲醚、三乙二醇乙基甲醚、三乙二醇丁基甲醚、三丙二醇二甲醚、四乙二醇二甲醚等。
在另一些优选的实施例中,按照本发明的组合物,所述的至少一种的有溶剂可选自基于酯的溶剂:辛酸烷酯、癸二酸烷酯、硬脂酸烷酯、苯甲酸烷酯、苯乙酸烷酯、肉桂酸烷酯、草酸烷酯、马来酸烷酯、烷内酯、油酸烷酯等。特别优选辛酸辛酯、癸二酸二乙酯、邻苯二甲酸二烯丙酯、异壬酸异壬酯。
所述的溶剂可以是单独使用,也可以是作为两种或多种有机溶剂的混合物使用。
在某些优选的实施例中,按照本发明的一种组合物,其特征在于,包含至少一种如上所述的有机化合物或高聚物或混合物及至少一种有机溶剂,还可进一步包含另一种有机溶剂。另一种有机溶剂的例子包括(但不限于):甲醇、乙醇、2-甲氧基乙醇、二氯甲烷、三氯甲烷、氯苯、邻二氯苯、四氢呋喃、苯甲醚、吗啉、甲苯、邻二甲苯、间二甲苯、对二甲苯、1,4二氧杂环己烷、丙酮、甲基乙基酮、1,2二氯乙烷、3-苯氧基甲苯、1,1,1-三氯乙烷、1,1,2,2-四氯乙烷、醋酸乙酯、醋酸丁酯、二甲基甲酰胺、二甲基乙酰胺、二甲基亚砜、四氢萘、萘烷、茚和/或它们的混合物。
一些优选的实施例中,特别适合本发明的溶剂是汉森(Hansen)溶解度参数在以下范围内的溶剂:
δd(色散力)在17.0~23.2MPa1/2的范围,尤其是在18.5~21.0MPa1/2的范围;
δp(极性力)在0.2~12.5MPa1/2的范围,尤其是在2.0~6.0MPa1/2的范围;
δh(氢键力)在0.9~14.2MPa1/2的范围,尤其是在2.0~6.0MPa1/2的范围。
按照本发明的组合物,其中有机溶剂在选取时需考虑其沸点参数。本发明中,所述的有机溶剂的沸点≥150℃;优选为≥180℃;较优选为≥200℃;更优为≥250℃;最优为≥300℃。这些范围内的沸点对防止喷墨印刷头的喷嘴堵塞是有益的。所述的有机溶剂可从溶剂体系中蒸发,以形成包含功能材料薄膜。
在一个优选的实施方案中,按照本发明的组合物是一溶液。
在另一个优选的实施方案中,按照本发明的组合物是一悬浮液。
本发明实施例中的组合物中可以包括0.01wt%至10wt%的按照本发明的化合物或混合物,较好的是0.1wt%至15wt%,更好的是0.2wt%至5wt%,最好的是0.25wt%至3wt%。
本发明还涉及所述组合物作为涂料或印刷油墨在制备有机电子器件时的用途,特别优选的是通过打印或涂布的制备方法。
其中,适合的打印或涂布技术包括(但不限于)喷墨打印,喷印(NozzlePrinting),活版印刷,丝网印刷,浸涂,旋转涂布,刮刀涂布,辊筒印花,扭转辊印刷,平版印刷,柔版印刷,轮转印刷,喷涂,刷涂或移印,狭缝型挤压式涂布等。首选的是凹版印刷,喷印及喷墨印刷。溶液或悬浮液可以另外包括一个或多个组份例如表面活性化合物,润滑剂,润湿剂,分散剂,疏水剂,粘接剂等,用于调节粘度,成膜性能,提高附着性等。有关打印技术,及其对有关溶液的相关要求,如溶剂及浓度,粘度等。
本发明还提供一种如上所述的芳香胺化合物、混合物或组合物在有机电子器件中的应用,所述的有机电子器件可选于,但不限于,有机发光二极管(OLED),有机光伏电池(OPV),有机发光电池(OLEEC),有机场效应管(OFET),有机发光场效应管,有机激光器,有机自旋电子器件,有机传感器及有机等离激元发射二极管(Organic Plasmon EmittingDiode)等,特别优选为OLED。本发明实施例中,优选将所述芳香胺化合物用于OLED器件的空穴传输层。
本发明进一步涉及一种有机电子器件,包含至少一功能层,所述功能层包含一种如上所述的芳香胺化合物、混合物或由上述的组合物制备而成。进一步地,所述有机电子器件,包含阴极、阳极和至少一功能层,所述功能层包含一种如上所述的芳香胺化合物或混合物或由上述的组合物制备而成。所述功能层选自空穴注入层(HIL)、空穴传输层(HTL)、发光层(EML)、电子阻挡层(EBL)、电子注入层(EIL)、电子传输层(ETL)、空穴阻挡层(HBL);优选地,所述功能层选自空穴传输层。
在一实施例中,按照本发明所述的有机电致发光器件,所述的有机功能层包含空穴注入层、第一空穴传输层、第二空穴传输层、发光层、电子传输层;所述第一空穴传输层在所述空穴注入层上方,所述第二空穴传输层在所述第一空穴传输层上方,所述发光层在所述第二空穴传输层上方,所述电子传输层在所述发光层上方;所述第二空穴传输层包含式(1)所示的芳胺类化合物。
所述的有机电子器件可选于,但不限于,有机发光二极管(OLED),有机光伏电池(OPV),有机发光电池(OLEEC),有机场效应管(OFET),有机发光场效应管,有机激光器,有机自旋电子器件,有机传感器及有机等离激元发射二极管(Organic Plasmon EmittingDiode)等,特别优选的是有机电致发光器件,如OLED,OLEEC,有机发光场效应管。
在以上所述的发光器件,特别是OLED中,包括一基片,一阳极,至少一发光层,一阴极。
基片可以是不透明或透明。一个透明的基板可以用来制造一个透明的发光元器件。例如可参见,Bulovic等Nature 1996,380,p29,和Gu等,Appl.Phys.Lett.1996,68,p2606。基片可以是刚性的或弹性的。基片可以是塑料,金属,半导体晶片或玻璃。最好是基片有一个平滑的表面。无表面缺陷的基板是特别理想的选择。在一个优选的实施例中,基片是柔性的,可选于聚合物薄膜或塑料,其玻璃化温度Tg为150℃以上,较好是超过200℃,更好是超过250℃,最好是超过300℃。合适的柔性基板的例子有聚(对苯二甲酸乙二醇酯)(PET)和聚乙二醇(2,6-萘)(PEN)。
阳极可包括一导电金属或金属氧化物,或导电聚合物。阳极可以容易地注入空穴到空穴注入层(HIL)或空穴传输层(HTL)或发光层中。在一个的实施例中,阳极的功函数和发光层中的发光体或作为HIL或HTL或电子阻挡层(EBL)的p型半导体材料的HOMO能级或价带能级的差的绝对值小于0.5eV,较好是小于0.3eV,最好是小于0.2eV。阳极材料的例子包括但不限于:Al、Cu、Au、Ag、Mg、Fe、Co、Ni、Mn、Pd、Pt、ITO、铝掺杂氧化锌(AZO)等。其他合适的阳极材料是已知的,本领域普通技术人员可容易地选择使用。阳极材料可以使用任何合适的技术沉积,如一合适的物理气相沉积法,包括射频磁控溅射,真空热蒸发,电子束(e-beam)等。在某些实施例中,阳极是图案结构化的。图案化的ITO导电基板可在市场上买到,并且可以用来制备根据本发明的器件。
阴极可包括一导电金属或金属氧化物。阴极可以容易地注入电子到EIL或ETL或直接到发光层中。在一个的实施例中,阴极的功函数和发光层中发光体或作为电子注入层(EIL)或电子传输层(ETL)或空穴阻挡层(HBL)的n型半导体材料的LUMO能级或导带能级的差的绝对值小于0.5eV,较好是小于0.3eV,最好是小于0.2eV。原则上,所有可用作OLED的阴极的材料都可能作为本发明器件的阴极材料。阴极材料的例子包括但不限于:Al、Au、Ag、Ca、Ba、Mg、LiF/Al、MgAg合金、BaF2/Al、Cu、Fe、Co、Ni、Mn、Pd、Pt、ITO等。阴极材料可以使用任何合适的技术沉积,如一合适的物理气相沉积法,包括射频磁控溅射,真空热蒸发,电子束(e-beam)等。
OLED还可以包含其他功能层,如空穴注入层(HIL)、空穴传输层(HTL)、电子阻挡层(EBL)、电子注入层(EIL)、电子传输层(ETL)、空穴阻挡层(HBL)。适合用于这些功能层中的材料在上面及在WO2010135519A1、US20090134784A1和WO2011110277A1中有详细的描述,特此将此3篇专利文件中的全部内容并入本文作为参考。
按照本发明的发光器件,其发光波长在550到700nm之间,较好的是在600到650nm之间,更好的是在600到640nm之间。
本发明还涉及按照本发明的电致发光器件在各种电子设备中的应用,包含,但不限于,显示设备,照明设备,光源,传感器等等。
下面将结合优选实施例对本发明进行了说明,但本发明并不局限于下述实施例,应当理解,所附权利要求概括了本发明的范围在本发明构思的引导下本领域的技术人员应意识到,对本发明的各实施例进行的一定的改变,都将被本发明的权利要求书的精神和范围所覆盖。
具体实施例
1.化合物的合成
实施例1:化合物A的合成
将化合物1(0.1mol),化合物2(0.2mol),Pd(dba)2 1.72g(0.003mol),t-Bu3P17.2mL(0.009mol),NatOBu 38.44g(0.4mol)溶于500mL无水甲苯,90℃下搅拌反应3小时。冷却至室温,加水终止反应,加乙酸乙酯萃取,收集有机相,有机相用无水硫酸镁干燥,过滤,旋干溶剂,使用硅胶层析法分离提纯,流动相为石油醚,得到47.9g实施例A,产率72%。MS:m/z测试值664.85g/mol。
实施例2:化合物B的合成
(1)中间体5的合成
将化合物3(0.1mol),化合物4(0.1mol),Pd(dba)2 1.72g(0.003mol),t-Bu3P17.2mL(0.009mol),NaOBu 19.22g(0.2mol)溶于500mL无水甲苯,90℃下搅拌反应3小时。冷却至室温,加水终止反应,加乙酸乙酯萃取,收集有机相,有机相用无水硫酸镁干燥,过滤,旋干溶剂,使用硅胶层析法分离提纯,流动相为石油醚/二氯甲烷混合溶剂(VPE:VDCM=10:1),得到21.7g中间体5,产率60%。MS:m/z测试值361.49g/mol。
(2)化合物B的合成
与化合物A的合成步骤类似,区别在于将化合物2替换为中间体5,最后得化合物B。MS:m/z测试值897.18g/mol。
实施例3:化合物C的合成
(1)中间体8的合成
与中间体5的合成步骤类似,区别在于将化合物3替换为化合物6,化合物4替换为化合物7,最后得中间体8。MS:m/z测试值335.41g/mol。
(2)化合物C的合成
与化合物A的合成步骤类似,区别在于将化合物2替换为中间体8,最后得化合物C。MS:m/z测试值845.01g/mol。
实施例4:化合物D的合成
(1)中间体10的合成
与中间体5的合成步骤类似,区别在于将化合物4替换为化合物9,最后得中间体10。MS:m/z测试值295.39g/mol。
(2)化合物D的合成
与化合物A的合成步骤类似,区别在于将化合物2替换为中间体10,最后得化合物D。MS:m/z测试值764.97g/mol。
实施例5:化合物E的合成
(1)中间体11的合成
与实施例A的合成步骤类似,区别在于将化合物2替换为中间体5,中间体5的当量与化合物1相同,最后得中间体11。MS:m/z测试值616.60g/mol。
(2)化合物E的合成
与化合物A的合成步骤类似,区别在于将化合物2替换为化合物12,化合物1替换为中间体11,化合物12和中间体11的当量相同,最后得化合物E。MS:m/z测试值857.11g/mol。
实施例6:化合物F的合成
(1)中间体15的合成
与中间体5的合成步骤类似,区别在于将化合物3替换为化合物13,将化合物4替换为化合物14,最后得中间体15。MS:m/z测试值275.37g/mol。
(2)中间体16的合成
与实施例A的合成步骤类似,区别在于将化合物2替换为中间体15,中间体15的当量与化合物1相同,最后得中间体16。MS:m/z测试值530.48g/mol。
(3)化合物F的合成
与化合物A的合成步骤类似,区别在于将化合物1替换为中间体16,中间体16的当量与化合物2相同,最后得化合物F。MS:m/z测试值694.90g/mol。
实施例7:化合物G的合成
(1)中间体18的合成
与中间体5的合成步骤类似,区别在于将化合物4替换为化合物17,最后得中间体18。MS:m/z测试值410.52g/mol。
(2)化合物G的合成
与化合物A的合成步骤类似,区别在于将化合物2替换为中间体18,最后得化合物G。MS:m/z测试值995.24g/mol。
实施例8:化合物H的合成
(1)中间体21的合成
将化合物19(0.1mol),化合物20(0.1mol),Pd(dba)2 1.72g(0.003mol),t-Bu3P17.2mL(0.009mol),NatOBu 38.44g(0.4mol)溶于500mL无水甲苯,90℃下搅拌反应3小时。冷却至室温,加水终止反应,加乙酸乙酯萃取,收集有机相,有机相用无水硫酸镁干燥,过滤,旋干溶剂,使用硅胶层析法分离提纯,流动相为石油醚,得到40.1g中间体21,产率91%。MS:m/z测试值441.26g/mol。
(2)化合物H的合成
将中间体21(0.2mol)、化合物1(0.1mol)溶于1,4-二氧六环与水(210/2ml)的混合溶剂中,并加入Pd(PPh3)4(5mmol)和碳酸钾(0.3mol)。在氮气气氛下,100℃搅拌6h。冷却后,旋蒸除去大部分溶剂,然后萃取并水洗分液,有机相柱层析并重结晶得到化合物H摩尔量为0.073mol,产率:73%。MS:m/z测试值969.45g/mol
2、OLED器件的制备及表征
下面通过具体实施例来详细说明采用上述的OLED器件的制备过程,红光OLED器件的结构为:ITO/HI/HT-1/HT-2/EML/ET:Liq/Liq/Al。
器件实施例1:
a、ITO(铟锡氧化物)导电玻璃基片的清洗:使用各种溶剂(例如氯仿、丙酮或异丙醇中的一种或几种)清洗,然后进行紫外臭氧处理;
b、蒸镀:将ITO基片移入真空气相沉积设备中,在高真空(1×10-6毫巴)下,采用电阻加热蒸发源形成厚度为30nm的空穴注入层(材料为化合物HI),在空穴注入层层上依次加热形成60nm的第一空穴传输层(材料为HT-1),紧接着在第一空穴传输层上蒸镀化合物A形成10nm的第二空穴传输层。随后RH置于一个蒸发单元,并且将化合物RD置于另外一个蒸发单元作为掺杂剂,使材料按不同速率气化,使得RH:RD的重量比在100:3,在第二空穴传输层上形成40nm的发光层。接着将ET和Liq置于不同的蒸发单元,使其分别以50重量%的比例进行共沉积,在发光层上形成30nm的电子传输层,随后在电子传输层上沉积1nm的Liq作为电子注入层,最后在所述电子注入层上沉积厚度为100nm的Al阴极。
c、封装:器件在氮气手套箱中用紫外线硬化树脂封装。
器件实施例2至8,对比例1至4的实施方法同器件实施例1,选用的HT-2层的材料如表1所示。
对上述实施例和对比例的器件性能进行测试,其中驱动电压、电流效率是在10mA/cm2电流密度下进行测试;T95的器件寿命是指在恒定电流密度50mA/cm2亮度衰减至95%的时间。结构如表1所示:
表1
和对比例1至4相比,器件实施例1至8的电流效率和寿命都有明显的提升,说明本发明的化合物应用于OLED器件中,可以提升器件的电流效率和寿命,同时还可以降低器件的驱动电压。
以上所述实施例的各技术特征可以进行任意的组合,为使描述简洁,未对上述实施例中的各个技术特征所有可能的组合都进行描述,然而,只要这些技术特征的组合不存在矛盾,都应当认为是本说明书记载的范围。
以上所述实施例仅表达了本发明的几种实施方式,其描述较为具体和详细,但并不能因此而理解为对发明专利范围的限制。应当指出的是,对于本领域的普通技术人员来说,在不脱离本发明构思的前提下,还可以做出若干变形和改进,这些都属于本发明的保护范围。因此,本发明专利的保护范围应以所附权利要求为准。
Claims (10)
2.根据权利要求1所述的芳香胺化合物,其特征在于,L1-L6独立选自单键或苯基。
4.根据权利要求1至3任一项所述的芳香胺化合物,其特征在于,所述的Ar1-Ar4独立选自以下所示结构中的任意一种:
其中:
X选自N或CR1;
Y选自O、S、S=O、SO2、NR2、PR2、CR2R3或SiR2R3;
R1-R3每次出现时,分别独立选自:氢,D,具有1至20个C原子的直链烷基,具有1至20个C原子的直链烷氧基,具有1至20个C原子的直链硫代烷氧基,具有3至20个C原子的支链烷基或环状的烷基,具有3至20个C原子的支链烷氧基或环状的烷氧基,具有3至20个C原子的支链硫代烷氧基或环状的硫代烷氧基,甲硅烷基,具有1至20个C原子的酮基,具有2至20个C原子的烷氧基羰基,具有7至20个C原子的芳氧基羰基,氰基,氨基甲酰基,卤甲酰基、甲酰基,异氰基,异氰酸酯基,硫氰酸酯基,异硫氰酸酯基,羟基,硝基,CF3,Cl,Br,F,可交联的基团,具有6至20个环原子的取代或未取代的芳香基团,具有5至20个环原子的取代或未取代的杂芳香基团,具有5至20个环原子的芳氧基,具有5至20个环原子的杂芳氧基基团,或这些基团的组合。
8.一种混合物,其特征在于,包含一种权利要求1至7任一项所述的芳香胺化合物,及至少另一种有机功能材料,所述另一种有机功能材料选自空穴注入材料、空穴传输材料、电子传输材料、电子注入材料、电子阻挡材料、空穴阻挡材料、发光材料、主体材料和有机染料中的至少一种。
9.一种组合物,其特征在于,包含至少一种权利要求1至7任一项所述的芳香胺化合物,或权利要求8所述的混合物,及至少一种有机溶剂。
10.一种有机电子器件,包含一功能层,其特征在于,所述功能层包含一种如权利要求1至7任一项所述的芳香胺化合物,或如权利要求8所述的混合物,或由权利要求9所述的组合物制备而成。
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