CN116390959A - 一种高聚物、包含其的组合物、有机光电器件及应用 - Google Patents
一种高聚物、包含其的组合物、有机光电器件及应用 Download PDFInfo
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- CN116390959A CN116390959A CN202180069479.2A CN202180069479A CN116390959A CN 116390959 A CN116390959 A CN 116390959A CN 202180069479 A CN202180069479 A CN 202180069479A CN 116390959 A CN116390959 A CN 116390959A
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- C08F112/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
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- C08F130/04—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
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Abstract
提供一种高聚物、包含其的混合物、组合物、有机光电器件及应用,其中,所述高聚物在侧链上包括一重复结构单元E,此重复结构单元包含B和/或N,具有较窄的发光谱,从而便于实现较高的色纯度;提供一种适合于印刷工艺的高聚物,进而降低有机光电器件特别是OLED的制造成本。
Description
本发明涉及电致发光材料领域,尤其涉及一种高聚物,包含其的组合物、有机光电器件,及高聚物在有机光电器件中的应用,特别是在有机光致发光和电致发光器件中的应用。本发明还涉及包含有按照本发明的高聚物的有机光电器件,及其制备方法。
因为有机半导体材料的在合成上的多样性,实现大面积柔性器件的可能,低的制造成本和高性能的光学和电学性能,有机发光二极管(OLED)在新颖的光电器件的实现中,例如,在平板显示器和照明应用,有很大的潜力。为了提高有机发光二极管的发光效率,各种基于荧光和磷光发光材料体系已被开发出来。使用磷光材料的有机发光二极管已经取得相当高的性能,如已取得了几乎100%的内部发光量子效率。但迄今为止,有实际使用价值的磷光材料是铱和铂配合物,原材料稀有而昂贵,配合物的合成很复杂,因此有相当高的成本。另外,铱和铂配合物虽然可以实现高效的发光效率,但发光谱线都较宽,造成色纯度不高。Hatakeyama等在2016年发现一类BN化合物(参见Hatakeyama等,Adv.Mater.2016,DOI:10.1002/adma.201505491),具有高的发光效率,同时具有很窄的FWHM。
为了充分利用有机材料的优点,人们希望通过打印的方法,低成本,大面积地制备OLED。现有报道的BN化合物及其类似物,分子量比较低,且结构刚性不适合于印刷工艺。
因此,新的适合于印刷的新材料体系有待于开发。
发明内容
鉴于上述现有技术的不足,本发明的目的在于提供一种高聚物、包含其的组合物、有机光电器件及应用,旨在提供一种新的高聚物材料,解决现有材料不适合于印刷工艺的问题。
本发明的技术方案如下:
一种高聚物,包括有如化学式I所示的重复单元:
其中n大于或等于1,X选自O,S,CR
1R
2,SiR
1R
2,NR
3,重复单元E选自如下化学式(1)或(2)的结构单元:
其中使用的符号与标记具有以下含义:
Ar
1~Ar
3相同或不同的选自具有5-24个环原子的芳香族或杂芳香族;
Ar
4~Ar
5相同或不同的选自空或具有5-24个环原子的芳香族或杂芳香族;
当Ar
4~Ar
5不为空时,X
a,X
b选自N、C(R
9)、Si(R
9);Y
a,Y
b选自B、P=O、C(R
9)、Si(R
9);
当Ar
4~Ar
5为空时,相应的X
a或Y
b选自N(R
9)、C(R
9R
10)、Si(R
9R
10)、C=O、O、C=N(R
9)、C=C(R
9R
10)、P(R
9)、P(=O)R
9、S、S=O或SO
2;
X1、X2是空或一个桥接基团;
R
1~R
10可相同或不同的选自取代基分别独立选自H、D、-F,-Cl,Br,I,-CN,-NO
2,-CF
3,具有1至20个C原子的直链的烷基、卤代烷基、烷氧基、硫代烷氧基基团,或者具有3至20个C原子的支链或环状的烷基、卤代烷基、烷氧基、硫代烷氧基基团或者是甲硅烷基基团,或具有1至20个C原子的取代的酮基基团,或具有2至20个C原子的烷氧基羰基基团,或具有7至20个C原子的芳氧基羰基基团,氰基基团(-CN),氨基甲酰基基团(-C(=O)NH
2),卤甲酰基基团(-C(=O)-X其中X代表卤素原子),甲酰基基团(-C(=O)-H),异氰基基团,异氰酸酯基团,硫氰酸酯基团或异硫氰酸酯基团,羟基基团,硝基基团,CF
3基团,Cl,Br,F,可交联的基团或者具有5至40个环原子的取代或未取代的芳族或杂芳族环系,或具有5至40个环原子的芳氧基或杂芳氧基基团,或具有5至40个环原子的芳胺基或杂芳胺基基团,以上取代基任意位置的二取代单元或这些体系的组合,其中一个或多个取代基团可以彼此和/或与所述基团键合的环形成单环或多环的脂族或芳族环系;
一种混合物,包括如上所述的高聚物,及至少另一种有机功能材料。
一种组合物,包括如上所述的高聚物,及至少一种有机溶剂和/或一种有机树脂。
一种有机光电器件,包括一种如上所述的高聚物。
有益效果:本发明的高聚物在有机溶剂中具有较好的溶解性,成膜性能好,同时保持单体窄的发光谱线,从而为印刷OLED提供了较好的材料解决方案。
本发明提供一种高聚物及其在有机电致发光器件中的应用,及包含有此高聚物的有机光电器件及其制备方法,为使本发明的目的、技术方案及效果更加清楚、明确,以下对本发明进一步详细说明。应当理解,此处所描述的具体实施例仅仅用以解释本发明,并不用于限定本发明。
本发明提供一种高聚物,包括有如化学式I所示的重复单元:
其中n大于或等于1,X选自O,S,CR
1R
2,SiR
1R
2,NR
3,重复单元E选自如下化学式(1)或(2)的结构单元:
其中使用的符号与标记具有以下含义:
Ar
1~Ar
3相同或不同的选自具有5-24个环原子的芳香族或杂芳香族;
Ar
4~Ar
5相同或不同的选自空或具有5-24个环原子的芳香族或杂芳香族;
当Ar
4~Ar
5不为空时,X
a,X
b选自N、C(R
9)、Si(R
9);Y
a,Y
b选自B、P=O、C(R
9)、Si(R
9);
当Ar
4~Ar
5为空时,相应的X
a或Y
b选自N(R
9)、C(R
9R
10)、Si(R
9R
10)、C=O、O、C=N(R
9)、C=C(R
9R
10)、P(R
9)、P(=O)R
9、S、S=O或SO
2;
X
1、X
2是空或一个桥接基团;
R
1~R
10可相同或不同的选自取代基分别独立选自H、D、-F,-Cl,Br,I,-CN,-NO
2,-CF
3,具有1至20个C原子的直链的烷基、卤代烷基、烷氧基、硫代烷氧基基团,或者具有3至20个C原子的支链或环状的烷基、卤代烷基、烷氧基、硫代烷氧基基团或者是甲硅烷基基团,或具有1至20个C原子的取代的酮基基团,或具有2至20个C原子的烷氧基羰基基团,或具有7至20个C原子的芳氧基羰基基团,氰基基团(-CN),氨基甲酰基基团(-C(=O)NH
2),卤甲酰基基团(-C(=O)-X其中X代表卤素原子),甲酰基基团(-C(=O)-H),异氰基基团,异氰酸酯基团,硫氰酸酯基团或异硫氰酸酯基团,羟基基团,硝基基团,CF
3基团,Cl,Br,F,可交联的基团或者具有5至40个环原子的取代或未取代的芳族或杂芳族环系,或具有5至40个环原子的芳氧基或杂芳氧基基团,或具有5至40个环原子的芳胺基或杂芳胺基基团,以上取代基任意位置的二取代单元或这些体系的组合,其中一个或多个取代基团可以彼此和/或与所述基团键合的环形成单环或多环的脂族或芳族环系。
在一个优选的实施例中,X选自CR
1R
2;特别优选的,X选自CH
2。
在某些优选的实施例中,桥连基团X
1、X
2至少有一个是空;特别好的是两个都为空,所述的重复结构单元E选自包含如下化学式(1b)或(2b)或所示的结构单元:
在一些较为优选的实施例中,X
1、X
2至少有一个是单键;特别优先的是,两个都为单键,所述的重复结构单元E选自包含如下化学式(1c)或(2c)所示的结构单元:
在某些实施例中,X
1、X
2在每一次出现时,相同或不同的是二桥联基,优选的二桥联基有:
其中符号R
3、R
4与R
5定义同如上所述的R
1,而上述基团所示虚线键表示与相邻的结构单元键合的键。
对于本发明的目的,芳香环系在环系中包含
个碳原子,杂芳香环系在环系中包含
个碳原子和至少一个杂原子,条件是碳原子和杂原子的总数至少为4。杂原子优选选自Si、N、P、O、S和/或Ge,特别优选选自Si、N、P、O和/或S。对于本发明的目的,芳香族或杂芳香族环系不仅包括芳香基或杂芳香基的体系,而且,其中多个芳基或杂芳基也可以被短的非芳族单元间断(<10%的非H原子,优选小于5%的非H原子,比如C、N或O原子)。因此,比如9,9′-螺二芴,9,9-二芳基芴,三芳胺,二芳基醚等体系,对于该发明目的同样认为是芳香族环系。
对于本发明的目的,其中NH上的H原子或桥联基CH
2基团可以被R
1基团取代;优先的,R
1可选于,(1)C1~C10烷基,特别优选是指如下的基团:甲基、乙基、正丙基、异丙基、环丙基、正丁基、异丁基、仲丁基、叔丁基、环丁基、2-甲基丁基、正戊基、正己基、环己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、三氟甲基、五氟甲基、2,2,2-三氟乙基、乙烯基、丙烯基、丁烯基、戊烯基、环戊烯基、己烯基、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、己炔基和辛炔基;(2)
烷氧基,特别优选的是指甲氧基,乙氧基,正丙氧基,异丙氧基,正丁氧基,异丁氧基,仲丁氧基,叔丁氧基或者2-甲基丁氧基;(3)C2到C10芳基或杂芳基,取决于用途其可以是一价或二价的,在每一情况下也可以被上述提及的基团R
1取代并可以通过任何希望的位置与芳香族或杂芳香环连接,特别优选的是指以下的 基团:苯、萘、蒽、嵌二萘、二氢芘、屈、茈、萤蒽、丁省、戊省、苯并芘、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、硫芴、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、吩恶嗪、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、恶唑、苯并恶唑、萘并恶唑、蒽并恶唑、菲并恶唑、异恶唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、吡嗪、二氮蒽、1,5-二氮杂萘、氮咔唑、苯并咔啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-恶二唑、1,2,4-恶二唑、1,2,5-恶二唑、1,3,4-恶二唑、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、中氮茚和苯并噻二唑。用于本发明的目的,芳香和杂芳族环系认为特别是除上述提及的芳基和杂芳基之外,还指亚联苯基、亚三联苯、芴、螺二芴、二氢菲、四氢芘和顺式或者反式茚并芴。
在一个优选的实施例中,包含化学式(1)-(1e)或(2)-(2e)的化合物,其中Ar
1~Ar
5相同或不同的在每一次出现中可选自具有5到20个环原子的芳香、杂芳族;较好的选自具有5到18个环原子的芳香、杂芳族;更好的选自具有5到15个环原子的芳香、杂芳族;最好的选自具有5到10个环原子的芳香、杂芳族;它们可以未被取代或者被一个或二个R
1基团取代。优选的芳基或者杂芳基有苯、萘、蒽、菲、吡啶、嵌二萘或噻吩。
在另一个优先的实施例中,Ar
1~Ar
5包含有如下结构式,它们各自可能被一个或多个基团R
1取代。
X
3是CR
6或N;
Y
7选自CR
7R
8,SiR
9R
10,NR
6或,C(=O),S,或O;R
6,R
7,R
8,R
9,R
10的定义如上所述。
进一步,Ar
1、Ar
2、Ar
3、Ar
4、Ar
5可独立选自如下化学结构式之一或其组合,其可进一步被任意取代:
对于本发明的目的,按化学式(1)-(1e)或(2)-(2e)的结构单元,在一个特别优选的实施例中,Ar
1~Ar
5为苯基。
在一个特别优先的实施例中,按照本发明的高聚物,所述的重复结构单元E包含如下化学式(1a)或(2a)所示的结构单元:
其中,X
1和X
2优先选自O,S,特别优先选自O。
在另一个特别优先的实施例中,按照本发明的高聚物,所述的重复结构单元E包含如下化学式(1d)或(2d)或(1e)或(2e)所示的结构单元:
优先的,化学式(2d)和(2e)中的Y
b相同或不同的彼此独立的选自C=O、O、P(=O)R
9、S=O或SO
2;特别优先的选自C=O。
优先的,化学式(1d)和(1e)中的X
a相同或不同的彼此独立的选自N(R
9)、C(R
9R
10)、Si(R
9R
10)、O、S。
在某些优选的实施例中,按照化学所(1),(2),(1a)-(1e),(2a)-(2e)的结构单元中,其中R
4~R
8在多次出现时,可相同或不同地包含以下结构单元或它们中的组合:
其中n是1或2或3或4。
在本发明实施例中,对于有机材料的能级结构,三线态能级(T1)及单线态能级(S1)、HOMO、LUMO、起着关键的作用。以下对这些能级的确定作一介绍。
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T1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 03W(Gaussian Inc.),具体的模拟方法可参见WO2011141110。
有机材料的单线态能级S1,可通过吸收光谱,或发射光谱来确定,也可通过量子模拟计算(如Time-dependent DFT)得到。
应该注意,HOMO、LUMO、T1及S1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、T1及S1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。
按照本发明的高聚物,其的好处是,重复单元E通过非共轭的高聚物主链连接起来,达到较高的分子量,同时保持单个重复单元能量结构,即单个重复单元的HOMO,LUMO,S1和T1基本保持不变。
在某些优先的实施例中,△(S1(E)-T1(E))≤0.30eV,较好是≤0.25eV,更好是≤0.20eV,更更好是≤0.15eV,最好是≤0.10eV。
按照本发明的高聚物,E是一个发光体。一般来说发光体在发光层中的比重有一定的范围。在某些的实施例中,重复单元E在高聚物中的含量是从0.1mol%≤90mol%。
在一个优先的实施例中,重复单元E在高聚物中的含量是从1mol%到80mol%,较好是从2mol%到70mol%,更好是从3mol%到50mol%,最好是从3mol%到30mol%。
在本发明实施例中,主体材料、基质材料、Host材料和Matrix材料具有相同的含义,可以互换。
在本发明实施例中,单线态,单重态具有相同的含义,可以互换。
在本发明实施例中,三线态,三重态具有相同的含义,可以互换。
本文中所定义的术语“小分子”是指不是聚合物,低聚物,树枝状聚合物,或共混物的分子。特别是,小分子中没有重复结构。小分子的分子量≤3000克/摩尔,较好是≤2000克/摩尔,最好是≤1500克/摩尔。
高聚物,即Polymer,包括均聚物(homopolymer),共聚物(copolymer),镶嵌共聚 物(block copolymer)。另外在本发明中,高聚物也包括树状物(dendrimer),有关树状物的合成及应用请参见【Dendrimers and Dendrons,Wiley-VCH Verlag GmbH & Co.KGaA,2002,Ed.George R.Newkome,Charles N.Moorefield,Fritz Vogtle.】。
共轭高聚物(conjugated polymer)是一高聚物,它的主链backbone主要是由C原子的sp2杂化轨道构成,著名的例子有:聚乙炔polyacetylene和poly(phenylene vinylene),其主链上的C原子的也可以被其他非C原子取代,而且当主链上的sp2杂化被一些自然的缺陷打断时,仍然被认为是共轭高聚物。另外在本发明中共轭高聚物也包括主链上包含有芳基胺(aryl amine)、芳基磷化氢(aryl phosphine)及其他杂环芳烃(heteroarmotics)、有机金属络合物(organometallic complexes)等。
在本发明中,重复结构单元E,在多个出现时,可以各自独立的选自相同或不同的结构基团。
在一些优先的实施例中,所述的高聚物,其光致发光谱线的半高宽(FWHM)≤55nm,较好是≤45nm,更好是≤40nm,特别好市≤35nm,最好是≤30nm。
下面给出合适的可作为按照本发明的重复结构单元的例子,其可任意进一步被任意取代:
在一个优选的实施例中,按照本发明的高聚物还包含有另一种的有机功能基团。
在某些实施例中,按照本发明的高聚物具有如下通式:
其中Y的定义如上所述X的定义,F为所述的另一种的有机功能基团,n,m为大于或等于1的整数。
所述另一种的有机功能基团F,在多个出现时,可相互独立地相同或不同地选于空穴(也称电洞)注入或传输基团,空穴阻挡基团,电子注入或传输基团,电子阻挡基团,有机基质基团,单重态发光基团(荧光发光基团),三重态发光基团(磷光发光基团)。这些有机功能基团都对应与相应的小分子有机功能材料:空穴(也称电洞)注入或传输材料(HIM/HTM),空穴阻挡材料(HBM),电子注入或传输材料(EIM/ETM),电子阻挡材料(EBM),有机基质材料(Host),单重态发光体(荧光发光体),三重态发光体(磷光发光体),热激发延迟荧光材料(TADF)。例如在WO2010135519A1、US20090134784A1和WO 2011110277A1中对这些有机功能材料有详细的描述,特此将此3篇专利文件中的全部内容并入本文作为参考。
在一个优先的实施例中,按照本发明的高聚物包含有前述的E,和另一种的有机功能基团F,其中F选自三重态基质基团。
在另一个优先的实施例中,按照本发明的高聚物包含有前述的E,和另一种的有机功能基团F,其中F选自三重态发光基团。
在另一个优先的实施例中,按照本发明的高聚物包含有前述的E,和另一种的有机功能基团F,其中F选自TADF发光基团。
在另一个优先的实施例中,按照本发明的高聚物包含有前述的E,和另外二种的有机功能基团F1和F2,其中F1选自三重态基质基团,F2选自三重态发光基团。
在另一个优先的实施例中,按照本发明的高聚物包含有前述的E,和另外二种的有机功能基团F1和F2,其中F1选自空穴传输基团,F2选自电子传输基团。
在一个较为优先的实施例中,按照本发明的高聚物包含有前述的E,和另一种的有机功能基团F,其中F选自单重态基质基团。
在另一个更为优先的实施例中,按照本发明的高聚物包含有前述的E,和另外二种的有机功能基团F1和F2,其中F1选自单重态基质基团,F2选自单重态发光基团。
下面对单重态基质基团和三重态基质基团作一些较详细的描述(但不限于此)。
1、三重态基质材料(TripletHost):
三重态主体材料的例子并不受特别的限制,任何金属络合物或有机化合物都可能被用作为主体,只要其三重态能级比发光体,特别是三重态发光体或磷光发光体更高。
可用作三重态主体(Host)的金属络合物的例子包括(但不限于)如下的一般结构:
M是一金属;(Y
3-Y
4)是一两齿配体,Y
3和Y
4独立地选自C,N,O,P,和S;L是一个辅助配体;m是一整数,其值从1到此金属的最大配位数;在一个优先的实施方案中,可用作三重态主体的金属络合物有如下形式:
(O-N)是一两齿配体,其中金属与O和N原子配位.m是一整数,其值从1到此金属的最大配位数;
在某一个实施方案中,M可选于Ir和Pt。
可作为三重态主体的有机化合物的例子选自包含有环芳香烃基的化合物,例如苯、联苯、三苯基苯、苯并芴;包含有芳香杂环基的化合物,如二苯并噻吩、二苯并呋喃、二苯并硒吩、呋喃、噻吩、苯并呋喃、苯并噻吩、苯并硒吩、咔唑、二苯并咔唑,吲哚咔唑、吡啶吲哚、吡咯二吡啶、吡唑、咪唑、三唑类、恶唑、噻唑、恶二唑、恶三唑、二恶唑、噻二唑、吡啶、哒嗪、嘧啶、吡嗪、三嗪类、恶嗪、恶噻嗪、恶二嗪、吲哚、苯并咪唑、吲唑、恶唑、二苯并恶唑、苯异恶唑、苯并噻唑、喹啉、异喹啉、邻二氮杂萘、喹唑啉、喹喔啉、萘、酞、蝶啶、氧杂蒽、吖啶、吩嗪、吩噻嗪、吩恶嗪、苯并呋喃吡啶、呋喃并吡啶、苯并噻吩吡啶、噻吩吡啶、苯并硒吩吡啶和硒吩苯并二吡啶;包含有2至10环结构的基团,它们可以是相同或不同类型的环芳香烃基团或芳香杂环基团,并彼此直接或通过至少一个以下的基团连结在一起,如氧原子、氮原子、硫原子、硅原子、磷原子、硼原子、链结构单元和脂肪环基团。其中,每个Ar可以进一步被取代,取代基可选为氢、氘、氰基、卤素、烷基、烷氧基、氨基、烯、炔、芳烷基、杂烷基、芳基和杂芳基。
在一个优先的实施方案中,三重态主体材料可选于包含至少一个以下基团的化合物:
其中:当Y多次出现时,Y各自独立地选于C(R)
2或NR或O或S;当X多次出现时,X各自独立地选于CR或N,Ar
1~Ar
3选于芳香基或杂芳香基,R可选于如下的基团:氢、氘、卤原子(F,Cl,Br,I)、氰基、烷基、烷氧基、氨基、烯基、炔基、芳烷基、杂烷基、芳基和杂芳基,n选自1到20的整数。
在下面的表中列出合适的三重态主体材料的例子但不局限于:
2、单重态基质材料(Singlet Host):
单重态主体材料的例子并不受特别的限制,任何有机化合物都可能被用作为主体,只要其单重态能量比发光体,特别是单重态发光体或荧光发光体更高。
作为单重态主体材料使用的有机化合物的例子可选自含有环芳香烃化合物,如苯、联苯、三苯基、苯并、萘、蒽、萉、菲、芴、芘、屈、苝、薁;芳香杂环化合物,如二苯并噻吩、二苯并呋喃、二苯并硒吩、呋喃、噻吩、苯并呋喃、苯并噻吩、苯并硒吩、咔唑、吲哚咔唑、吡啶吲哚、吡咯二吡啶、吡唑、咪唑、三氮唑、异恶唑、噻唑、恶二唑、恶三唑、二恶唑、噻二唑、吡啶、哒嗪、嘧啶、吡嗪、三嗪、恶嗪、恶噻嗪、恶二嗪、吲哚、苯并咪唑、吲唑、吲哚嗪、苯并恶唑、苯异恶唑、苯并噻唑、喹啉、异喹啉、噌啉、喹唑啉、喹喔啉、萘、酞、蝶啶、氧杂蒽、吖啶、吩嗪、吩噻嗪、吩恶嗪、苯并呋喃吡啶、呋喃二吡啶、苯并噻吩吡啶、噻吩二吡啶、苯并硒吩吡啶和硒吩二吡啶;包含有2至10环结构的基团,它们可以是相同或不同类型的环芳香烃基团或芳香杂环基团,并彼此直接或通过至少一个以下的基团连结在一起,如氧原子、氮原子、硫原子、硅原子、磷原子、硼原子、链结构单元和脂肪环基团。
在一个优先的实施方案中,单重态主体材料可选于包含至少一个以下基团的化合物:
Y每次出现时,独立选自C(R)
2或NR或O或S,X每次出现时,独立选自CR或N,R每次出现时,独立选自如下的基团:氢、氘、卤原子(F,Cl,Br,I)、氰基、烷基、烷氧基、氨基、烯基、炔基、芳烷基、杂烷基、芳基和杂芳基,n选自1到20的整数。
在一些优先的实施例中,单重态主体选自蒽的衍生物,如CN102224614 B、CN 100471827C、CN 1914293B、WO2015033559A1、US2014246657A1、WO2016117848A1、WO2016117861A1、WO2016171429A2、CN102369256B、CN102428158B等专利文献中所公开的。
下面的表中列出一些蒽基单重态主体材料的例子:
在一些更加优先的实施例中,蒽基单重态主体材料是氘代的,即主体材料分子中含有至少一个以上的氘原子,这样的例子在CN102369256B、CN102428158B、CN102639671B、US2015021586A1等专利文献中所公开。
本发明还提供一种可聚合的单体,具有如下通式,
其中结构单元E包含有如化学式(1)-(1e)或(2)-(2e)任一个所示的结构。
在一个优先的实施例中,所述的可聚合的单体,其特征在于,(S1(E)-T1(E))≤0.30eV,较好是≤0.25eV,更好是≤0.20eV,最好是≤0.10eV。
本发明还提供一种混合物,包含有至少一种如上所述的高聚物和另一种有机功能材料,所述有机功能材料可选于空穴(也称电洞)注入或传输材料(HIM/HTM),空穴阻挡材料(HBM),电子注入或传输材料(EIM/ETM),电子阻挡材料(EBM),有机基质材料(Host),单重态发光体(荧光发光体),三重态发光体(磷光发光体),及热激发延迟荧光材料(TADF)。这些功能材料前面已有所述。
本发明还涉及一种组合物,包含有一种如上所述的高聚物或可聚合单体及至少一种有机溶剂和/或一种有机树脂。
在一个优先的实施例中,所述的组合物包含一种有机溶剂。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。
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0.01至20wt%的高聚物,较好的是0.1至15wt%,更好的是0.2至10wt%,最好的是0.25至5wt%的高聚物。
在一个优先的实施例中,所述的组合物包含一种有机树脂。在另一个优先的实施例中,所述的组合物包含两种及以上的有机树脂。出于本发明的目的,所述的有机树脂是指树脂预聚体或其交联或固化后形成的树脂。
适合本发明的有机树脂,包括但不限制于:聚苯乙烯、聚丙烯酸酯、聚甲基丙烯酸酯、聚碳酸酯、聚胺酯、聚乙烯吡咯烷酮、聚乙酸乙烯酯、聚氯乙烯、聚丁烯、聚乙二 醇、聚硅氧烷、聚丙烯酸酯、环氧树脂、聚乙烯醇、聚丙烯腈、聚偏二氯乙烯(PVDC)、聚苯乙烯-丙烯腈(SAN)、聚对苯二甲酸丁二醇酯(PBT)、聚对苯二甲酸乙二醇酯(PET)、聚丁酸乙烯酯(PVB)、聚氯乙烯(PVC)、聚酰胺、聚甲醛、聚酰亚胺、聚醚酰亚胺或其混合物。
进一步,适合本发明的有机树脂,包含但不限制于由以下单体(树脂预聚体)均聚或共聚形成:苯乙烯衍生物、丙烯酸酯衍生物、丙烯腈衍生物、丙烯酰胺衍生物、乙烯酯衍生物、乙烯醚衍生物、马来酰亚胺衍生物、共轭二烯烃衍生物。
苯乙烯衍生物的例子有:烷基苯乙烯,如α-甲基苯乙烯,邻-、间-、对-甲基苯乙烯,对丁基苯乙烯,尤其是对叔丁基苯乙烯,烷氧基苯乙烯如对甲氧基苯乙烯、对丁氧基苯乙烯、对叔丁氧基苯乙烯。
丙烯酸酯衍生物的例子有:丙烯酸甲酯、甲基丙烯酸甲酯、丙烯酸乙酯、甲基丙烯酸乙酯、丙烯酸正丙酯、甲基丙烯酸正丙酯、丙烯酸异丙酯、甲基丙烯酸异丙酯、丙烯酸正丁酯、甲基丙烯酸正丁酯、丙烯酸异丁酯、甲基丙烯酸异丁酯、丙烯酸仲丁酯、甲基丙烯酸仲丁酯、丙烯酸叔丁酯、甲基丙烯酸叔丁酯、丙烯酸2-羟基乙酯、甲基丙烯酸2-羟基乙酯、丙烯酸2-羟基丙酯、甲基丙烯酸2-羟基丙酯、丙烯酸3-羟基丙酯、甲基丙烯酸3-羟基丙酯、丙烯酸2-羟基丁酯、甲基丙烯酸2-羟基丁酯、丙烯酸3-羟基丁酯、甲基丙烯酸3-羟基丁酯、丙烯酸4-羟基丁酯、甲基丙烯酸4-羟基丁酯、丙烯酸烯丙酯、甲基丙烯酸烯丙酯、丙烯酸苄酯、甲基丙烯酸苄酯、丙烯酸环己酯、甲基丙烯酸环己酯、丙烯酸苯酯、甲基丙烯酸苯酯、丙烯酸2-甲氧基乙酯、甲基丙烯酸2-甲氧基乙酯、丙烯酸2-苯氧基乙酯、甲基丙烯酸2-苯氧基乙酯、甲氧基二甘醇丙烯酸酯、甲氧基二甘醇甲基丙烯酸酯、甲氧基三甘醇丙烯酸酯、甲氧基三甘醇甲基丙烯酸酯、甲氧基丙二醇丙烯酸酯、甲氧基丙二醇甲基丙烯酸酯、甲氧基二丙二醇丙烯酸酯、甲氧基二丙二醇甲基丙烯酸酯、丙烯酸异冰片酯、甲基丙烯酸异冰片酯、丙烯酸双环戊二烯酯、甲基丙烯酸双环戊二烯酯、(甲基)丙烯酸金刚烷酯、(甲基)丙烯酸降冰片酯、丙烯酸2-羟基-3-苯氧基丙酯、甲基丙烯酸2-羟基-3-苯氧基丙酯、单丙烯酸甘油酯和单甲基丙烯酸甘油酯;丙烯酸2-氨基乙酯、甲基丙烯酸2-氨基乙酯、丙烯酸2-二甲基氨基乙酯、甲基丙烯酸2-二甲基氨基乙酯、N,N-二甲基氨基乙基(甲基)丙烯酸、N,N-二乙基氨基乙基(甲基)丙烯酸酯、丙烯酸2-氨基丙酯、甲基丙烯酸2-氨基丙酯、丙烯酸2-二甲基氨基丙酯、甲基丙烯酸2-二甲基氨基丙酯、丙烯酸3-氨基丙酯、甲基丙烯酸3-氨基丙酯、N,N-二甲基-1,3-丙二胺(甲基)丙烯酸苄酯、丙烯酸3-二甲基氨基丙酯和甲基丙烯酸3-二甲基氨基丙酯;丙烯酸缩水甘油酯和甲基丙烯酸缩水甘油酯;
丙烯腈衍生物的例子有:丙烯腈、甲基丙烯腈、α-氯丙烯腈和偏二氰基乙烯;
丙烯酰胺衍生物的例子有:丙烯酰胺、甲基丙烯酰胺、α-氯丙烯酰胺、N-2-羟乙基丙烯酰胺和N-2-羟乙基甲基丙烯酰胺;
乙烯酯衍生物的例子有:乙酸乙烯酯、丙酸乙烯酯、丁酸乙烯酯和苯甲酸乙烯酯;
乙烯醚衍生物的例子有:乙烯基甲基醚、乙烯基乙基醚和烯丙基缩水甘油基醚;
马来酰亚胺衍生物的例子有:马来酰亚胺、苄基马来酰亚胺、N-苯基马来酰亚胺和N-环己基马来酰亚胺;
共轭二烯烃衍生物的例子有:1,3-丁二烯、异戊二烯和氯丁二烯;
所述的均聚物或共聚物可以通过例如自由基聚合、阳离子聚合、阴离子聚合或有机金属催化聚合(例如Ziegler-Natta催化)进行制备。聚合的工艺可以是悬浮聚合、乳液聚合、溶液聚合或本体聚合。
所述的有机树脂通常具有10 000-1 000 000g/mol,优选20 000-750000g/mol,更优选30 000-500 000g/mol的平均摩尔质量Mn(由GPC测定)。
在一些优先的实施方案中,有机树脂为热固性树脂或紫外(UV)可固化树脂。在一些实施方案中,用将促进卷对卷加工的方法固化有机树脂。
热固性树脂需要固化,在固化中它们会经历不可逆的分子交联过程,这使得树脂不可熔化。在一些实施方案中,热固性树脂为环氧树脂、酚醛树脂、乙烯基树脂、三聚氰胺树脂、脲醛树脂、不饱和聚酯树脂、聚氨酯树脂、烯丙基树脂、丙烯酸类树脂、聚酰胺树脂、聚酰胺-酰亚胺树脂、酚胺缩聚树脂、脲三聚氰胺缩聚树脂或其组合。
在一些实施方案中,热固性树脂为环氧树脂。环氧树脂易于固化,不会放出挥发物或因广泛的化学品而生成副产物。环氧树脂也可与大多数基板相容并往往易于润湿表面。参见Boyle,M.A.等人,“Epoxy Resins”,Composites,Vol.21,ASM Handbook,pages 78-89(2001)。
在一些实施方案中,有机树脂为有机硅热固性树脂。在一些实施方案中,有机硅热固性树脂为0E6630A或0E6630B(Dow Corning Corporation(密歇根州奥本市))。
在一些实施方案中,使用热引发剂。在一些实施方案中,热引发剂为AIBN[2,2’-偶氮双(2-甲基丙腈)]或过氧化苯甲酰。
UV可固化树脂是在暴露于特定波长的光时将固化并快速硬化的聚合物。在一些实施方案中,UV可固化树脂为具有自由基聚合基团、阳离子可聚合基团作为官能团的树脂,所述自由基聚合基团为例如(甲基)丙烯酰氧基基团、乙烯基氧基基团、苯乙烯基基团或乙烯基基团;所述阳离子可聚合基团为例如环氧基基团、硫代环氧基基团、乙烯基氧基基团或氧杂环丁烷基基团。在一些实施方案中,UV可固化树脂为聚酯树脂、聚醚树脂、(甲基)丙烯酸类树脂、环氧树脂、聚氨酯树脂、醇酸树脂、螺缩醛树脂、聚丁二烯树脂或硫代烯树脂。
在一些实施方案中,UV可固化树脂选自聚氨酯丙烯酸酯、烯丙氧基化的二丙烯酸环己酯、双(丙烯酰氧基乙基)羟基异氰脲酸酯、双(丙烯酰氧基新戊基二醇)己二酸酯、双酚A二丙烯酸酯、双酚A二甲基丙烯酸酯、1,4-丁二醇二丙烯酸酯、1,4-丁二醇二甲基丙烯酸酯、1,3-丁二醇二丙烯酸酯、1,3-丁二醇二甲基丙烯酸酯、二环戊基二丙烯酸酯、二乙二醇二丙烯酸酯、二乙二醇二甲基丙烯酸酯、二季戊四醇六丙烯酸酯、二季戊四醇单羟基五丙烯酸酯、二(三羟甲基丙烷)四丙烯酸酯、三乙二醇二甲基丙烯酸酯、甲基丙烯酸甘油酯、1,6-己二醇二丙烯酸酯、新戊二醇二甲基丙烯酸酯、新戊二醇羟基新戊酸二丙烯酸酯、季戊四醇三丙烯酸酯、季戊四醇四丙烯酸酯、磷酸二甲基丙烯酸酯、聚乙二醇二丙烯酸酯、聚丙二醇二丙烯酸酯、四乙二醇二丙烯酸酯、四溴双酚A二丙烯酸酯、三乙二醇二乙烯基醚、二丙烯酸三甘油酯、三羟甲基丙烷三丙烯酸酯、三丙二醇二丙烯酸酯、三(丙烯酰氧基乙基)异氰脲酸酯、磷酸三丙烯酸酯、磷酸二丙烯酸酯、丙烯酸焕丙基酯、乙烯基封端聚二甲基硅氧烷、乙烯基封端二苯基硅氧烷-二甲基硅氧烷共聚物、乙烯基封端聚苯基甲基硅氧烷、乙烯基封端二氟甲基硅氧烷-二甲基硅氧烷共聚物、乙烯基封端二乙基硅氧烷-二甲基硅氧烷共聚物、乙烯基甲基硅氧烷、单甲基丙烯酰氧基丙基封端聚二甲基硅氧烷、单乙烯基封端聚二甲基硅氧烷、单烯丙基-单三甲基甲硅烷氧基封端聚环氧乙烷及其组合。
在一些实施方案中,UV可固化树脂为巯基官能化合物,其可在UV固化条件下与异氰酸酯、环氧树脂或不饱和化合物交联。在一些实施方案中,巯基官能化合物为多硫醇。在一些实施方案中,多硫醇为季戊四醇四(3-巯基丙酸酯)(PETMP);三羟甲基丙烷三(3-巯基丙酸酯)(TMPMP);乙二醇二(3-巯基丙酸酯)(GDMP);三[25-(3-巯基-丙酰氧基)乙基]异氰尿酸酯(TEMPIC);二季戊四醇六(3-巯基丙酸酯)(Di-PETMP);乙氧基化三羟甲基丙烷三(3-巯基丙酸酯)(ETTMP 1300和ETTMP 700);聚己内酯四(3-巯基丙酸酯)(PCL4MP1350);季戊四醇四巯基乙酸酯(PETMA);三羟甲基丙烷 三巯基乙酸酯(TMPMA);或乙二醇二巯基乙酸酯(GDMA)。这些化合物由Bruno Bock(德国马尔沙赫特)以商品名
出售。
在一些实施方案中,UV可固化树脂还包含光引发剂。光引发剂将在暴露于光的过程中引发光敏材料的交联和/或固化反应。在一些实施方案中,光引发剂是基于苯乙酮的、基于安息香的或基于噻吨酮的。
在一些实施方案中,UV可固化树脂包含巯基官能化合物和甲基丙烯酸酯、丙烯酸酯、异氰酸酯或其组合。在一些实施方案中,UV可固化树脂包括多硫醇和甲基丙烯酸酯、丙烯酸酯、异氰酸酯或其组合。
在一些实施方案中,光引发剂为MINS-311RM(Minuta Technology Co.,Ltd(韩国))。
在一些实施方案中,光引发剂为
127、
184、
184D、
2022、
2100、
250、
270、
2959、
369、
369EG、
379、
500、
651、
754、
784、
819、
819DW、
907、
907FF、
OxeOl、
TPO-L、
1173、
1173D、
4265,
BP或
MBF(BASF Corporation(密歇根州怀恩多特))。在一些实施方案中,光引发剂为TPO(2,4,6-三甲基苯甲酰-二苯基-氧化麟)或MBF(苯甲酰甲酸甲酯)。
在一些实施方案中,有机树脂按组合物的重量百分数(重量/重量)计在约50%至约99%、约50%至约95%、约50%至约90%、约50%至约85%、约50%至约80%、约50%至约70%、约50%至约60%、约60%至约99%、约60%至约95%、约60%至约90%、约60%至约85%、约60%至约80%、约60%至约70%、约70%至约99%、约70%至约95%、约70%至约90%、约70%至约85%、约70%至约80%、约80%至约99%、约80%至约95%、约80%至约90%、约80%至约85%、约85%至约99%、约85%至约95%、约85%至约90%、约90%至约99%、约90%至约95%、或约95%至约99%之间。
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光电器件时的用途,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,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,丝网印刷及喷墨印刷。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,的详细信息请参见Helmut Kipphan主编的《印刷媒体手册:技术和生产方法》(Handbook of Print Media:Technologies and Production Methods),ISBN 3-540-67326-1。
基于上述高聚物,本发明还提供一种如上所述的高聚物的应用,即将所述高聚物应用于有机光电器件,所述的有机光电器件可选于,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,有机自旋光电器件,有机传感器及有机等离激元发射二极管(Organic Plasmon Emitting Diode)等,特别是OLED。本发明实施例中,优选地将所述有机化合物用于OLED器件的发光层中。
在一个优先的实施例中,所述高聚物用于OLED器件的发光层。
本发明进一步涉及一种有机光电器件,至少包含一种如上所述的高聚物。一般的,此种有机光电器件至少包含一个阴极,一个阳极及位于阴极和阳极之间的一个功能层, 其中所述的功能层中至少包含一种如上所述的高聚物。所述的有机光电器件可选于,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,有机自旋光电器件,有机传感器及有机等离激元发射二极管(Organic Plasmon Emitting Diode),及颜色转换器件。
所述的颜色转换器件可以是下转换颜色转换器,用以制造彩色显示器,其中将蓝光转换成绿光和红光。
在一个特别优选的实施例中,所述的有机光电器件是OLED,其中包括一基片,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。
在一个优选的实施例中,按照本发明的发光器件中,其发光层是通过打印本发明的组合物制备而成。
按照本发明的发光器件,其发光波长在300到1000nm之间,较好的是在350到900nm之间,更好的是在400到800nm之间。
本发明还涉及按照本发明的有机光电器件在各种电子设备中的应用,包括,但不限于,显示设备,照明设备,光源,传感器等等。
本发明还涉及包含有按照本发明的有机光电器件的电子设备,包括,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所进行的一定的改变,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.单体的合成
⑴单体E1的合成
合成路线如下图所示:
合成步骤如下:
a.氮气环境保护下,将10mmol的化合物1溶解于250ml的干燥DMF溶液中,所得反应溶液置入冰浴中搅拌,逐滴加入11.0mmol的三氯氧磷(POCl
3)溶液,滴加完毕后,继续反应30分钟,逐渐升至室温并反应2小时,加水淬灭反应,二氯甲烷萃取,水洗涤,合并有机相,用无水硫酸钠干燥,过滤,蒸干有机溶剂,得化合物2的粗产物,粗产物用二氯甲烷与正已烷重结晶得产品7.5mmol,产率:75.0%。真空干燥待用。MS(ASAP)=448.2。
b.将上述所得5.0mmol化合物2溶解于200ml干燥的四氢呋喃(THF)溶液中,氮气环境保护下,反应液置于-78℃的温度下搅拌,逐滴加入8.0mmol亚甲基三苯基磷(Wittig试剂),待加入完毕后,逐渐升至室温,继续在室温下搅拌过夜,加水淬灭反应,所有反应液用二氯甲烷萃取,有机相用水洗涤,最后合并有机相,用无水硫酸钠干燥,过滤,蒸干有机溶剂,所得产物用硅胶柱纯化,流动相为三氯甲烷:石油醚=1:2,最后得到3.85mmol单体E1,产率:77.0%。真空环境下干燥待用。MS(ASAP)=446.2。
(2)单体E2的合成
合成路线如下图所示:
合成步骤如下:
a.合成方法与单体E1的合成方法相似,产率:74.8%。真空干燥待用。MS(ASAP)=728.4。
b.合成方法与单体E1的合成方法相似,产率:78.9%。真空环境下干燥待用。MS(ASAP)=726.4。
(3)单体E3的合成:
合成路线如下图所示:
合成步骤如下:
a.合成方法与单体E1的合成方法相似,产率:76.7%。真空干燥待用。MS(ASAP)=417.1。
b.合成方法与单体E1的合成方法相似,产率:79.5%。真空环境下干燥待用。MS(ASAP)=417.1。
(4)单体E4的合成:
合成路线如下图所示:
合成步骤如下:
a.氮气环境保护下,将10mmol的化合物1溶解于250ml的干燥THF溶液中,所得反应溶液置入冰浴中搅拌,逐滴加入11.0mmol的正丁基锂(n-BuLi)溶液,滴加完毕后,继续反应30分钟,滴入11.0mmol的DMF溶剂,滴加完毕后,逐渐升至室温并反应2小时,加水淬灭反应,二氯甲烷萃取,水洗涤,合并有机相,用无水硫酸钠干燥,过滤,蒸干有机溶剂,得化合物2的粗产物,粗产物用二氯甲烷与正已烷重结晶得产品7.55mmol,产率:75.5%。真空干燥待用。MS(ASAP)=545.2。
b.合成方法与单体E1的合成方法相似,产率:88.4%。真空环境下干燥待用。MS(ASAP)=543.2。
(5)单体E5的合成:
合成步骤如下:
a.合成方法与单体E4的合成方法相似,产率:74.7%。真空干燥待用。MS(ASAP)=723.3。
b.合成方法与单体E1的合成方法相似,产率:81.4%。真空环境下干燥待用。MS(ASAP)=721.3。
(5)单体F1的合成
合成实验路线如下图所示:
合成步骤如下:
a.氮气环境保护下,将10mmol的化合物1溶解于250ml的干燥THF溶液中,所得反应溶液置入冰浴中搅拌,逐滴加入11.0mmol的正丁基锂(n-BuLi)溶液,滴加完毕后,继续反应30分钟,滴入11.0mmol的DMF溶剂,滴加完毕后,逐渐升至室温并反应2小时,加水淬灭反应,二氯甲烷萃取,水洗涤,合并有机相,用无水硫酸钠干燥,过滤,蒸干有机溶剂,得化合物2的粗产物,粗产物用二氯甲烷与正已烷重结晶得产品7.8mmol,产率:78.0%。真空干燥待用。MS(ASAP)=685.2。
b.将上述所得5.0mmol化合物2溶解于200ml干燥的四氢呋喃(THF)溶液中,氮气环境保护下,反应液置于-78℃的温度下搅拌,逐滴加入8.0mmol亚甲基三苯基磷(Wittig试剂),待加入完毕后,逐渐升至室温,继续在室温下搅拌过夜,加水淬灭反应,所有反应液用二氯甲烷萃取,有机相用水洗涤,最后合并有机相,用无水硫酸钠干燥,过滤,蒸干有机溶剂,所得产物用硅胶柱纯化,流动相为二氯甲烷:石油醚=1:4,最后得到4.4mmol单体F1,产率:88.0%。真空环境下干燥待用。MS(ASAP)=683.2
(6)单体F2的合成
合成实验路线如下图所示:
合成步骤如下:
a.合成方法与单体F1的合成方法相似,产率:61.4%。真空干燥待用。MS(ASAP)=210.1。
b.合成方法与单体F1的合成方法相似,产率:45.8%。真空环境下干燥待用。MS(ASAP)=208.1。
(7)单体F3的合成
合成实验路线如下图所示:
合成步骤如下:
a.合成方法与单体F1的合成方法相似,产率:60.5%。真空干燥待用。MS(ASAP)=408.1。
b.合成方法与单体F1的合成方法相似,产率:67.4%。真空环境下干燥待用。MS(ASAP)=406.2。
(8)单体F4的合成
合成实验路线如下图所示:
合成步骤如下:
a.合成方法与单体F1的合成方法相似,产率:68.1%。真空干燥待用。MS(ASAP)=273.1。
b.合成方法与单体F1的合成方法相似,产率:78.4%。真空环境下干燥待用。MS(ASAP)=271.2。
2.高聚物的合成
对于高聚物的合成,其主要合成步骤如下:以P1聚合物的合成为例,在氮气保护条件下,将0.10mmolE1,0.40mmolF1及0.5molF5的单体溶解于苯溶剂中,同时用注射器加入0.01mmol 2,2-偶氮二异丁腈(AIBN引发剂),密封,在60℃下反应4小时,当反应完成后,冷却至室温,用甲醇来沉淀出聚合物。沉淀用四氢呋喃(THF)溶解,再用甲醇沉淀。如此重复
次,真空干燥,得到聚合物P1的固体。
对于P2~P13合成步骤与P1类似,不同的是含不同比例的乙烯基单体,对于P2~P13 所包含的单体及比例如下表所示:
高聚物 | E1 | E2 | E3 | E4 | E5 | F1 | F2 | F3 | F4 | F5 |
P1 | 10 | 40 | 50 | |||||||
P2 | 10 | 40 | 50 | |||||||
P3 | 10 | 40 | 50 | |||||||
P4 | 10 | 40 | 50 | |||||||
P5 | 10 | 40 | 50 | |||||||
P6 | 10 | 40 | 50 | |||||||
P7 | 10 | 40 | 50 | |||||||
P8 | 10 | 40 | 15 | 35 | ||||||
P9 | 10 | 40 | 15 | 35 | ||||||
P10 | 10 | 40 | 15 | 10 | 35 | |||||
P11 | 10 | 40 | 10 | 10 | 30 | |||||
P10 | 15 | 85 | ||||||||
P11 | 15 | 85 | ||||||||
P12 | 15 | 85 | ||||||||
P13 | 15 | 85 |
3.OLED器件的制备及测量
下面通过具体实施例来详细说明采用上述高聚物的OLED器件的制备过程,该OLED器件的结构为:ITO/HIL/HTL/EML/ETL/阴极,制备步骤如下:
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、HIL(空穴注入层,60nm):60nm的PEDOT(聚乙撑二氧噻吩,Clevios
TM AI4083)作为HIL在超净室旋转涂布而成,并在180℃的热板上处理10分钟;
c、HTL(空穴传输层,20nm):20nm的TFB是在氮气手套箱中通过旋转涂布而成,所用的溶液是TFB的甲苯溶剂溶液,溶度5mg/ml,随后在180℃的热板上处理60分钟;
其中,TFB(H.W.SandsCorp.)是一种空穴传输材料,用于HTL,其结构式如下:
d、EML(有机发光层):EML是在氮气手套箱中通过旋转涂布而成,所用的溶液是加入至甲苯溶剂的高聚物(P1-P9),溶液溶度10mg/ml,随后在180℃的热板上处理10分钟;表二列出器件的EML的组分和厚度;
表二
器件 | HTL | EML | 颜色 | V@1knits[V] | 效率@1knits[Cd/A] |
OLED1 | TFB | P1(65nm) | 蓝 | 6.5 | 5.5 |
OLED2 | TFB | P2(65nm) | 蓝 | 6.3 | 6.1 |
OLED3 | TFB | P3(80nm) | 蓝 | 7.1 | 6.2 |
OLED4 | TFB | P4(80nm) | 绿 | 4.5 | 62 |
OLED5 | TFB | P5(80nm) | 绿 | 4.8 | 58 |
OLED6 | TFB | P6(65nm) | 绿 | 7.0 | 41 |
OLED7 | TFB | P7(65nm) | 绿 | 6.6 | 45 |
OLED8 | TFB | P8(65nm) | 蓝 | 6.7 | 6.7 |
OLED9 | TFB | P9(80nm) | 绿 | 6.4 | 56 |
e、阴极:Ba/Al(2nm/100nm)在高真空(1×10
-6毫巴)中热蒸镀而成;
f、封装:器件在氮气手套箱中用紫外线固化树脂封装。
各OLED器件的电流电压及发光(IVL)特性通过表征设备来表征,同时记录重要的参数如效率,寿命及驱动电压。OLED器件的性能总结在表二中,所有OLED的发光谱的的FWHM都小于40nm。
4.颜色转换膜的制备
将高聚物(P10-P13)溶在甲苯溶剂里配成溶液,溶液溶度20mg/ml,在氮气手套箱中在基板上通过旋转涂布形成100-300nm的薄膜,随后在180℃的热板上处理10分钟。所得的薄膜可以用作颜色转换介质,其中P10,P11为蓝光,P12和P13为绿光,发光谱的FWHM都小于40nm。
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 (11)
- 一种高聚物,包括有如化学式I所示的重复单元:其中n大于或等于1,X选自O,S,CR 1R 2,SiR 1R 2,NR 3,重复单元E选自如下化学式(1)或(2)的结构单元:其中使用的符号与标记具有以下含义:Ar 1~Ar 3相同或不同的选自具有5-24个环原子的芳香族或杂芳香族;Ar 4~Ar 5相同或不同的选自空或具有5-24个环原子的芳香族或杂芳香族;当Ar 4~Ar 5不为空时,X a,X b选自N、C(R 9)、Si(R 9);Y a,Y b选自B、P=O、C(R 9)、Si(R 9);当Ar 4~Ar 5为空时,相应的X a或Y b选自N(R 9)、C(R 9R 10)、Si(R 9R 10)、C=O、O、C=N(R 9)、C=C(R 9R 10)、P(R 9)、P(=O)R 9、S、S=O或SO 2;X 1、X 2是空或一个桥接基团;R 1~R 10可相同或不同的选自取代基分别独立选自H、D、-F,-Cl,Br,I,-CN,-NO 2,-CF 3,具有1至20个C原子的直链的烷基、卤代烷基、烷氧基、硫代烷氧基基团,或者具有3至20个C原子的支链或环状的烷基、卤代烷基、烷氧基、硫代烷氧基基团或者是甲硅烷基基团,或具有1至20个C原子的取代的酮基基团,或具有2至20个C原子的烷氧基羰基基团,或具有7至20个C原子的芳氧基羰基基团,氰基基团(-CN),氨基甲酰基基团(-C(=O)NH 2),卤甲酰基基团(-C(=O)-X其中X代表卤素原子),甲酰基基团(-C(=O)-H),异氰基基团,异氰酸酯基团,硫氰酸酯基团或异硫氰酸酯基团,羟基基团,硝基基团,CF 3基团,Cl,Br,F,可交联的基团或者具有5至40个环原子的取代或未取代的芳族或杂芳族环系,或具有5至40个环原子的芳氧基或杂芳氧基基团,或具有5至40个环原子的芳胺基或杂芳胺基基团,以上取代基任意位置的二取代单元或这些体系的组合,其中一个或多个取代基团可以彼此和/或与所述基团键合的环形成单环或多环的脂族或芳族环系。
- 根据权利要求1所述的高聚物,其特征在于,其发光谱线的半高宽(FWHM)≤45nm。
- 一种混合物,包含有一种如权利要求1所述的高聚物,及至少另一种的有机功能材料,所述的至少另一种的有机功能材料选于空穴(也称电洞)注入或传输材料(HIM/HTM),空穴阻挡材料(HBM),电子注入或传输材料(EIM/ETM),电子阻挡材料(EBM),有机基质材料(Host),单重态发光体(荧光发光体),三重态发光体(磷光发光体)。
- 一种组合物,包含有一种如权利要求1所述的高聚物,至少一种有机溶剂和/或一种有机树脂。
- 一种有机光电器件,至少包括一种如权利要求1所述的高聚物。
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