CN101460434B - 用于有机电致发光器件的新材料 - Google Patents
用于有机电致发光器件的新材料 Download PDFInfo
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- CN101460434B CN101460434B CN200780020514.1A CN200780020514A CN101460434B CN 101460434 B CN101460434 B CN 101460434B CN 200780020514 A CN200780020514 A CN 200780020514A CN 101460434 B CN101460434 B CN 101460434B
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/72—Spiro hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/02—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/24—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a seven-membered ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
本发明涉及有机电致发光器件,特别是发蓝色光器件,其中通式(1)~(4)的化合物用作发光层中的主体材料或掺杂物和/或用作空穴传输材料和/或用作电子传输材料。
Description
本发明涉及有机半导体及其在有机电子器件中的用途。
正在开发用于最广义上归于电子工业的许多不同应用场合的有机半导体。例如在US 4539507、US 5151629、EP 0676461和WO 98/27136中描述了有机电致发光器件(OLEDs)的结构,在所述结构中这些有机半导体用作功能材料。然而,这些器件仍然存在相当大的,迫切需要改进的问题:
1.通常使用的化合物没有足够低的LUMO(最低空分子轨道)。为了更容易注入电子,并为了因而工作电压的降低,需要具有相对低LUMO的化合物。
2.在根据现有技术的体系中,通常在发光层的主体材料中使用一种或多种掺杂物。在发光层中具有能用作纯物质的化合物是明智的,因为这代表了在器件生产中技术的简化。
3.对于长寿命、高品位的应用,有机电致发光器件的寿命仍然不够。
4.目前用于有机电致发光器件中的许多有机化合物的热稳定性不够,这意味着在通过体相升华作用纯化材料中,以及在通过热蒸发施用材料期间会出现相当大的问题。特别是,通常用作发蓝色光化合物的、包含苯乙烯胺基团的化合物的施用。
主要稠合的芳香化合物,特别是蒽或芘衍生物,根据现有技术中作为主体材料用于荧光OLEDs,特别是用于发蓝色光的电致发光器件,例如9,10-双(2-萘基)蒽(US 5935721)。WO 03/095445和CN 1362464公开了9,10-双(1-萘基)蒽衍生物用于OLEDs中。其它的蒽衍生物公开于WO0 1/076323,WO 01/021729,WO 04/013073,WO 04/018588,WO 03/087023或WO 04/018587中。基于芳基取代的芘和屈的主体材料公开于WO 04/016575中。对于高性能的应用,有必要利用改进的主体材料。
作为发蓝色光化合物的现有技术,可以提及使用芳基乙烯基胺(例如WO 04/013073、WO 04/016575、WO 04/018587)。然而,这些化合物是热不稳定的,不能在没有分解的情况下蒸发,因此对于合成和OLED制造需要高度复杂的技术,因此表现出技术缺点。另外的缺点是这些化合物的发光颜色:尽管在现有技术中描述了这些化合物的深蓝色发光(CIE y坐标为0.15~0.18),但根据现有技术在简单的器件中不能再现这些彩色坐标。相反,此处得到绿蓝色发光。使用这些化合物如何真实地产生蓝色发光是不明显的。因此,对于高品位的应用场合,有必要具有可用的、改进的发光体,特别关于器件和升华稳定性以及发光颜色。
在磷光OLEDs中,使用的基质材料通常是4,4′-双(N-咔唑基)联苯(CBP)。缺点是用其制造的器件寿命短且通常工作电压高,这导致低的功率效率。另外,CBP具有不足够高的玻璃化转变温度。而且,已经发现CBP不适于发蓝色的电致发光器件,这导致效率低下。另外,包括CBP的器件结构复杂,因为必须额外使用空穴阻挡层和电子传输层。基于酮化合物的改进的三重态基质材料描述于WO 04/093207中。然而,在其中公开的最好的基质材料的合成中需要有毒的无机氰化物,因此,这些材料的制备是生态学上不可接受的。那里描述的其它基质材料的玻璃化转变温度仍不够。
用于有机电致发光器件中的电子传输化合物通常是AlQ3(三羟基喹啉铝)(US 4539507)。这有许多缺点:由于它在升华温度下部分分解,它不能在不留下残余物的情况下蒸汽沉积,这代表了主要的问题,特别是对于生产装置。另外的缺点是AlQ3的高吸湿性,以及低的电子迁移率,这导致较高的电压,并因而导致较低的功率效率。为了防止显示器中的短路,希望增加所述层的厚度;由于低的电荷载流子迁移率,以及结果发生的电压增加,这在使用AlQ3时是不可能的。而且,AlQ3的固有颜色(在固体时为黄色),由于再吸收和弱的再发光,能导致彩色偏移,特别是在蓝色OLEDs中,这被证明是非常不利的。这里仅能制造效率或颜色定位有相当大的减小的蓝色OLEDs。尽管存在所述缺点,但迄今为止AlQ3还是代表了满足OLEDs中电子传输材料各种要求的最佳折衷方案。
因此,仍旧需要改进的材料,特别是用于蓝色荧光发光体和三线态发光体的主体材料,以及发光化合物(特别是发蓝色光化合物)、空穴传输材料和电子传输物料,它们是热稳定的,在有机电子器件中导致良好的效率同时具有长寿命,在器件的制造与操作中给出可重复的结果,以及容易合成获得,并且有高的产率和高的热稳定性。
令人惊讶地,已经发现其中亚苯基团与两个萘基基团在对位连接的化合物,以及这些化合物的杂环衍生物非常高度适合在有机电致发光器件中使用,所述化合物中该萘基基团可以经由1-或2-位连接至亚苯基,并且其中,另外在每一情况下,在亚苯基团和两个萘基基团之间,存在至少一个桥连。这些化合物具有高的热稳定性。而且,使用这些材料,与现有技术的材料相比,增加有机电子器件的效率和寿命是可能的。此外,因为它们具有非常高的玻璃化转变温度,因此这些材料高度适合用于有机电子器件。因此,本发明涉及这些材料及其在有机电子器件,特别是有机电致发光器件中的用途。
本发明涉及通式(1)~通式(4)的化合物,
通式(1) 通式(2)
通式(3)
通式(4)
其中以下应用于符号和标记:
Y 每一次出现相同或不同,是CR1或N;
Z 如果桥连X结合至基团Z,则等于C,并且如果没有桥连基X结合至基团Z,则等于Y;
X 每一次出现相同或不同,是选自B(R1)、C(R1)2、Si(R1)2、C=O、C=NR1、C=C(R1)2、O、S、S=O、SO2、N(R1)、P(R1)和P(=O)R1的二价桥连;
R1 每一次出现相同或不同,是H,F,Cl,Br,I,N(Ar)2,C(=O)Ar,P(=O)Ar2,S(=O)Ar,S(=O)2Ar,CR2=CR2Ar,CN,NO2,Si(R2)3,B(OR2)2,OSO2R2,具有1~40个碳原子的直链烷基、烷氧基或硫代烷氧基,或者具有3~40个碳原子的支链或环状烷基、烷氧基或硫代烷氧基,它们每个可被一个或多个基团R2取代,并且其中一个或多个非相邻的CH2基团可以被R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S或CONR2替代,且其中一个或多个H原子可以被F、Cl、Br、I、CN或NO2替代,或者具有5~40个芳环原子的芳香或杂芳环系,在每一情况下所述环系可以被一个或多个基团R2取代,或者具有5~40个芳环原子的芳氧基或杂芳氧基基团,它们可被一个或多个基团R2取代,或者这些体系的的组合;此处两个或多个相邻的取代基R1还可以彼此形成单或多环的脂肪或芳香环系;
Ar 每一次出现相同或不同,是具有5~30个芳环原子的芳香或杂芳环系,它们可被一个或多个非芳基R1取代;此处两个在相同的氮或磷原子上的基团Ar,还可以通过单键或桥连X彼此连接;
R2 每一次出现相同或不同,是H或具有1~20个碳原子的脂肪、芳香和/或杂芳烃基,其中另外H原子可以被F替代;此处两个或多个相邻的取代基R2还可以彼此形成单或多环的脂肪或芳香环系;
a,b,c,d 每一次出现相同或不同,是0或1,条件是a+b=1或2并且c+d=1或2,其中在每一情况下a=0和b=0和c=0和d=0,意味着不存在相应的桥连X;
以下化合物除外:
通式(1)~通式(4)化合物优选具有的玻璃化转变温度Tg大于70℃,特别优选大于100℃,非常特别优选大于130℃。
为了本发明的目的,相邻的基团R1和R2认为意思是基团或者结合至相同的碳原子,或者结合至相同的杂原子,或者结合至相邻的碳原子或杂原子。
为了本发明的目的,芳基包含6~40个碳原子;为了本发明的目的,杂芳基包含2~40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5。杂原子优选选自N、O和/或S。本发明的芳基或者杂芳基认为是指单个芳香环,即苯,或者单个杂芳环,例如吡啶、嘧啶、噻吩等,或者稠合的芳基或者杂芳基基团,例如萘、蒽、芘、喹啉、异喹啉等。
为了本发明的目的,芳香环系在环系中包含6~40个碳原子。为了本发明的目的,杂芳环系在环系中包含2~40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5。杂原子优选选自N、O和/或S。为了本发明的目的,芳香或杂芳环系认为是指不仅仅包括芳基或杂芳基的体系,而且还包含其中多个芳基或杂芳基可以被短的非芳族单元(小于10%的原子不同于H)间断的体系,所述非芳族单元例如sp3-杂化的C、N或O原子。因此,诸如9,9′-螺二芴、9,9-二芳基芴、三芳基胺、二芳基醚、芪等体系,为了本发明的目的同样被认为是芳香环系。
为了本发明的目的,其中另外单个H原子或CH2基团可以被上述基团取代的C1~C40烷基特别优选认为是指如下基团: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、环戊基、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、五氟乙基、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、环已烯基、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、己炔基或者辛炔基。C1~C40烷氧基特别优选认为是指甲氧基、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、叔丁氧基或者2-甲基丁氧基。在每一情况下还可以被上述基团R取代,以及可以经由任何希望的位置连接至芳香或杂芳环系,具有5~40个芳环原子的芳香或杂芳环系特别是指源于如下的基团:苯、萘、蒽、菲、芘、、茈、萤蒽、丁省、戊省、苯并芘、联苯、亚联苯、三联苯、亚三联苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式或者反式茚并芴、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、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-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、中氮茚和苯并噻二唑。
优选通式(1)~(4)的结构,其中a+b=1且c+d=1。
优选的通式(1)~(4)的化合物选自通式(5)、(6)、(7)、(8)、(9)、(10)、(11)、(12)、(13)、(14)、(15)或(16)的结构,
通式(5) 通式(6)
通式(7) 通式(8)
通式(9) 通式(10)
通式(11) 通式(12)
通式(13) 通式(14)
通式(15) 通式(16)
其中符号X和Y具有如上所述相同的含义。
进一步优选通式(1)~通式(16)的化合物,其中符号Y代表氮的总次数为0、1、2、3或4,其中别的符号Y代表CR1。特别优选通式(1)~通式(16)的化合物,其中符号Y代表氮的总次数为0、1或2。在本发明一个特别优选实施方式中,符号Y代表CR1。
在非常特别优选的实施方案中,通式(1)~(4)的结构选自通式(5a)、(6a)、(7a)、(8a)、(9a)、(10a)和(11a),
通式(5a) 通式(6a)
通式(7a) 通式(8a)
通式(9a) 通式(10a)
通式(11a)
其中符号X和R1具有如上所述相同的含义。
在通式(5a)~(11a)的结构中,两个基团R1在每一情况下特别优选不同于氢。
此外优选通式(1)~(16)和(5a)~(11a)的化合物,其中符号R1每一次出现相同或不同,代表H,F,Br,C(=O)Ar,P(=O)Ar2,CR2=CR2Ar,具有1~5个碳原子的直链烷基或具有3~5个碳原子的支链烷基,其中一个或多个CH2基团可被-R2C=CR2-、-C≡C-或-O-替代,且其中一个或多个H原子可被F替代,或者具有6~16个碳原子的芳基或具有2~16个碳原子的杂芳基,或螺二芴基团,它们每个可被一个或多个基团R2取代,或者这些体系两个或三个的组合。特别优选的基团R1每一次出现相同或不同,是H、F、Br、C(=O)Ar、P(=O)Ar2、甲基、乙基、异丙基、叔丁基,其中一个或多个H原子可被F替代,或者具有6~14个碳原子的芳基,或螺二芴基团,它们的每个可被一个或多个基团R2取代,或者这些体系的两个的组合。
当并入聚合物、低聚物或树枝状高分子中时,以及在化合物自溶液加工的情况下,还优选具有高达10个碳原子的线性或支化烷基链。为了该化合物用作制备根据本发明其它化合物的中间体,或用作制备聚合物的单体,特别优选溴作为取代基。
进一步优选通式(1)~(16)和(5a)~(11a)的化合物,其中至少一个符号R1代表通式(17)或(18)的基团N(Ar)2,
通式(17) 通式(18)
其中R2具有上述含义,此外:
E 代表单键、O、S、N(R2)或C(R2)2;
Ar1每一次出现相同或不同,是具有5~20个芳环原子的芳基或杂芳基基团,或具有15~30个芳环原子的三芳基胺基团,它们每个可被一个或多个基团R2取代,优选具有6~14个芳环原子的芳基或杂芳基,或具有18~22个芳环原子的三芳基胺基团,它们每个可被一个或多个基团R2取代;
p 每一次出现相同或不同,是0或者1。
特别优选上述通式(5a)~(11a)的化合物,其中基团R1代表通式(17)或通式(18)的基团。
Ar1相同或不同,特别优选代表苯基,邻、间或对甲基苯基,对氟苯基,1-萘基,2-萘基,三苯基胺,萘基二苯基胺,或二萘基苯基胺。
还优选通式(1)~(16)和(5a)~(11a)的化合物,其中符号X每一次出现相同或不同,是选自C(R1)2、C=O、C=NR1、O、S、S=O、SO2、N(R1)、P(R1)和P(=O)R1的二价桥连。特别优选通式(1)~(16)和(5a)~(11a)的化合物,其中符号X每一次出现相同或不同,选自C(R1)2、N(R1)、P(R1)和P(=O)(R1),非常特别优选C(R1)2和N(R1),特别是C(R1)2。此处应该再一次明确指出,多个相邻的基团R1在这里同样可以彼此形成芳香或脂肪环系。如果在基团C(R1)2上的多个基团R1彼此形成环系,这导致螺结构。通过在C(R1)2上的两个基团R1之间形成环系而形成该类型的螺结构,是本发明另外优选的实施方案。这特别适用于如果R1代表取代或未取代苯基,而且两个苯基与桥连X一起形成环系的情况。
优选的结合至桥连X的基团R1相同或不同,选自H,具有1~5个碳原子的直链烷基或具有3~5个碳原子的支链烷基,其中在每一情况下一个或多个非相邻的CH2基团可被-R2C=CR2-、-C≡C-或-O-替代,且其中一个或多个H原子可被F替代,或者具有6~16个碳原子的芳基或具有2~16个碳原子的杂芳基,它们的每个可被一个或多个基团R2取代,或者这些体系的两个或三个的组合;此处两个结合至相同桥原子的基团R1,还可以彼此形成环系。结合至桥连X,特别优选的基团R1相同或不同,选自甲基、乙基、异丙基、叔丁基,其中在每一情况下一个或多个H原子可被F替代,或者具有6~14个碳原子的芳基,所述芳基可被一个或多个基团R2取代,或者这些体系的两个的组合;此处结合至相同桥原子的两个基团R1也可以彼此形成环系。当并入聚合物、低聚物或树枝状高分子中,以及在化合物自溶液加工的情况下,还优选具有高达10个碳原子的直链或支链烷基链。
进一步优选对称的和对称取代的化合物,即其中符号X相同的化合物。在通式(5a)~(11a)结构中,取代基R1进一步优选选择为相同。
通式(1)~通式(16)和(5a)~(11a)的优选化合物的实例是以下描述的结构(1)~(132)。
上述根据本发明的化合物,特别是被反应性离去基团例如溴、碘、硼酸或硼酸酯取代的化合物,还能用作制造相应的共轭、部分共轭或非共轭聚合物、低聚物的共聚单体,或者作为树枝状高分子的核。此处优选经由卤素官能团或硼酸官能团进行聚合。
因此本发明进一步涉及聚合物、低聚物或树枝状高分子,其包含通式(1)~(16)和(5a)~(11a)的一种或多种化合物,其中一个或多个基团R1代表从通式(1)~(16)和(5a)~(11a)的化合物至聚合物或树枝状高分子的结合。这些聚合物、低聚物或树枝状高分子可以是共轭的、部分共轭或非共轭的。
如上所述相同的优选适用于通式(1)~(16)或(5a)~(11a)的重复单元。
这些化合物均聚或与另外的单体共聚。适当和优选的共聚单体选自芴(例如见EP 842208或WO 00/22026),螺二芴(例如见EP 707020,EP 894107或WO 06/061181),对苯撑(例如见WO 92/18552),咔唑(例如见WO 04/070772和WO 04/113468),噻吩(例如见EP 1028136),二氢菲(例如见WO 05/014689),顺式和反式茚并芴(例如见WO 04/041901和WO 04/113412),酮(例如见WO05/040302),菲(例如见WO 05/104264或未公开申请DE102005037734.3),或选自多个这些单元。这些聚合物通常还包含其它的单元,例如发光(荧光或磷光)单元,比如乙烯基三芳基胺(例如,根据未公开申请DE 102005060473.0)或磷光金属配合物(例如,根据WO 06/003000),和/或电荷传输单元,特别是基于三芳基胺的那些单元。
根据本发明通式(1)~(16)和(5a)~(11a)的化合物能通过本领域普通技术人员已知的合成步骤制备。因此,能通过例如相应叔醇的酸催化环化制备不同的骨架,如在示意图1中对于通式(1)的化合物的通常条件所示。该骨架能通过标准方法官能化,例如通过Friedel-Crafts烷基化或酰化。而且,该骨架能通过有机化学的标准方法溴化。溴化的化合物代表了用于进一步官能化的基础。因此,它们能与芳基硼酸或芳基硼酸衍生物通过Suzuki偶联反应,或与有机锡化合物通过Stille方法反应得到广泛的芳香化合物。通过Hartwig-Buchwald方法偶联至芳香或脂族胺,得到相应的胺。而且,溴化的衍生物能通过锂化反应和与亲电子试剂例如苯基腈反应转变为酮,随后酸性水解,或者通过与氯代二苯基膦反应,接着通过氧化成为氧化膦。
示意图1
如果在第一偶联步骤中使用2-萘基硼酸而不是1-萘硼酸,上述方法会完全类似地导致通式(3)或通式(4)的化合物。
而且,溴化化合物或者直接,或者在转化为硼酸衍生物之后,能用作制造聚合物、低聚物或树枝状高分子的单体。
在该合成中,取决于合成条件,会形成5-元环/5-元环衍生物,6-元环/6-元环衍生物,5-元环/6-元环衍生物,或者这些化合物的混合物。这些能或者进一步分离和处理为纯化合物,或它们还可以作为混合物使用。
本发明还涉及用于合成通式(1)~(4)化合物的方法,其包括以下步骤:
a)
将官能化的萘与四官能化的苯衍生物偶联;
b)
任选进一步官能化苯衍生物上的官能团;
c)
用酸催化闭环;以及
d)
通过步骤a)~c)得到的母体结构通过溴化而官能化,随后通过Hartwig-Buchwald偶联至芳香胺,或通过Suzuki偶联至芳基硼酸或芳基硼酸衍生物。
在萘上的官能团此处优选是硼酸基团或硼酸衍生物。在苯衍生物上用于偶联的两个官能团优选是氯、溴或碘,特别优选溴。在苯衍生物上的另外两个官能团优选是通式C(=O)-O-R的两个酯基,其中R代表具有1~20个碳原子的烷基。在步骤b)中能够进行进一步官能化,例如通过加入有机锂化合物,得到叔醇。
通式(1)~通式(16)和(5a)~(11a)的化合物适于在有机电致发光器件(OLEDs,PLEDs)中使用。取决于取代,该化合物能用于OLED中不同的功能和层中。
因此,本发明还涉及通式(1)~(16)和(5a)~(11a)的化合物,特别是如上所述优选实施方案,在有机电子器件,特别是在有机电致发光器件中的用途。
本发明还进一步涉及有机电子器件,其包括至少一种选自通式(1)~(16)和(5a)~(11a)化合物的化合物,特别是涉及有机电致发光器件,所述有机电致发光器件包括阳极、阴极和至少一层发光层,特征在于至少一层包括至少一种选自通式(1)~(16)和(5a)~(11a)化合物的化合物,特别是如上所述的优选实施方案。
除了阴极,阳极和发光层,所述有机电致发光器件还可以包含另外的层。这些层能选自,例如:空穴注入层、空穴传输层、电子传递层、电子注入层和/或电荷产生层(IDMC 2003,台湾;Session 21 OLED(5),T.Matsumoto,T.Nakada,J.Endo,K.Mori,N.Kawamura,A.Yokoi,J.Kido,Multiphoton Organic EL Device Having ChArge GenerationLayer)。然而,应该指出指出这些层的每一个没有必要都存在。
在本发明另外优选实施方式中,该有机电致发光器件包括多层发光层,其中至少一层包括至少一种通式(1)~(16)和(5a)~(11a)的化合物。这些发光层特别优选在380nm和750nm之间具有总的多个发光最大值,总体得到白色发光,即在该发光层中使用能够发荧光或发磷光以及发黄色光、发橙色光或发红色光的各种发光化合物。特别优选三层体系,其中这些层的至少一层包括通式(1)~(16)和(5a)~(11a)的化合物,并且其中所述三层显示蓝色、绿色以及橙色或者红色发光(对于基本结构,例如见WO 05/011013)。同样适合于白色发光的是具有宽波段发光波段的发光体,因此显示白色发光。
在本发明的实施方式中,通式(1)~(16)和(5a)~(11a)的化合物用作用于荧光掺杂物的主体。在这种情况下,一个或多个取代基R1优选选自简单或稠合的芳基或杂芳基,特别是苯基,邻-、间-或对联苯基,1-或2-萘基,蒽基,特别是苯基蒽基或者1-或2-萘基蒽基,2-芴基和2-螺二芴基,它们的每个可被一个或多个基团R2取代。特别是应用于通式(5a)~(11a)结构上的基团R1。
主体材料被认为是在包括主体和掺杂物的体系中以较高比例存在的组分。在包括主体和多种掺杂物的体系中,该主体认为意思是在该混合物中比例最高的组分。
在发光层中,根据本发明的主体材料的比例在50.0wt%与99.9wt%之间,优选在80.0wt%与99.5wt%之间,特别优选在90.0wt%与99.0wt%之间。相应地,在掺杂物中的比例在0.1wt%与50.0wt%之间,优选在0.5wt%与20.0wt%之间,特别优选在1.0wt%与10.0wt%之间。
在荧光器件中,优选的掺杂物选自以下种类:单苯乙烯基胺、二苯乙烯基胺、三苯乙烯基胺、四苯乙烯基胺和芳基胺。单苯乙烯基胺认为是指包含一个苯乙烯基和至少一个优选芳香族的胺的化合物。二苯乙烯基胺认为是指包含两个苯乙烯基和至少一个优选芳香族的胺的化合物。三苯乙烯基胺认为是指包含三个苯乙烯基和至少一个优选芳香族的胺的化合物。四苯乙烯基胺认为是指包含四个苯乙烯基和至少一个优选芳香族的胺的化合物。为了本发明的目的,芳基胺或芳香胺认为是如下的化合物,包含三个直接与氮结合的芳香或杂芳环系,如果在该体系中没有苯乙烯基,则其中至少一个优选是具有至少14个芳环原子的稠环体系。苯乙烯基基团特别优选是芪,其也可以进一步在双键或芳环上被取代。该类型掺杂物的实例是取代或未取代的三芪胺,或其它例如描述在如下文献中的掺杂物:WO 06/000388、WO06/058737、WO 06/000389和未公开专利申请DE 102005058543.4和DE 102006015183.6。另外,优选如WO 06/122630中描述的化合物,同样优选以下提及的根据本发明的通式(1)~(16)和(5a)~(11a)的掺杂物。
在本发明另外的实施方式中,通式(1)~(16)和(5a)~(11a)的化合物用作用于荧光掺杂物的基质。在这种情况下,一个或多个取代基R1和/或桥连X优选包含至少一个基团C=O、P(=O)和/或SO2。这些基团特别优选直接结合至根据本发明的中心单元,而且特别优选还包含一个,或在氧化膦情况下两个其它芳香取代基。特别是应用于通式(5a)~(11a)结构上的基团R1。
在磷光器件中,所述掺杂物优选选自这类金属络合物,其包括至少一种原子序数大于20的元素,优选大于38小于84,特别优选大于56小于80。优选使用包含铜、钼、钨、铼、钌、锇、铑、铱、钯、铂、银、金或铕的金属配合物,特别是包含铱或铂的金属配合物。如根据现有技术使用的磷光材料通常适合本目的。
在本发明又一其它实施方式中,通式(1)~(16)和(5a)~(11a)的化合物用作发光材料。该化合物适合作为发光化合物,特别是如果至少一个取代基R1包含至少一个乙烯基芳基单元、至少一个乙烯基芳胺单元和/或至少一个二芳基胺单元N(Ar)2的情况。这特别适用于在通式(5a)~(11a)结构上的基团R1。在通式(5a)~(11a)结构上的两个基团R1优选选择相同。
在发光层混合物中,通式(1)~(16)和(5a)~(11a)发光化合物的比例在0.1wt%与50.0wt%之间,优选在0.5wt%与20.0wt%之间,特别优选在1.0wt%与10.0wt%之间。相应地,主体材料的比例在50.0wt%与99.9wt%之间,优选在80.0-99.5wt%之间,特别优选在90.0wt%与99.0wt%之间。
适合该目的的主体材料是不同种类的物质。优选的主体材料选自如下种类:低聚亚芳基(例如2,2′,7,7′-四苯基螺二芴,如EP676461中所述,或者二萘基蒽),特别是含稠合芳香基团的低聚亚芳基,低聚亚芳基亚乙烯基(例如DPVBi或者螺-DPVBi,如EP 676461中所述),多配体的金属络合物(例如如WO 04/081017中所述),空穴导电化合物(例如,如WO 04/058911中所述),电子导电化合物,特别是酮、氧化膦、亚砜等(例如,如WO 05/084081和WO 05/084082中所述),阻转异构体(例如WO 06/048268中所述)或者硼酸衍生物(例如WO06/117052中所述)。而且,适合的主体材料还有上述根据本发明的通式(1)~(16)和(5a)~(11a)的化合物。除根据本发明的化合物之外,特别优选的主体材料选自如下的种类:含萘、蒽和/或芘的低聚亚芳基,或者这些化合物的阻转异构体,低聚亚芳基亚乙烯基,酮,氧化膦和亚砜。除根据本发明的化合物之外,非常特别优选的主体材料选自如下种类:包含蒽和/或芘的低聚亚芳基或这些化合物的阻转异构体,氧化膦和亚砜,特别是被两个可以相同或不同的芳基取代的蒽衍生物。为了本发明的目的,低聚亚芳基是指其中至少三个芳基或亚芳基基团彼此结合的化合物。
在本发明又一其它实施方式中,通式(1)~(16)和(5a)~(11a)的化合物用作空穴传输材料或空穴注入材料。该化合物然后优选被至少一个基团N(Ar)2取代,优选被至少两个基团N(Ar)2取代。基团N(Ar)2优选选自上述通式(17)和(18)。这特别适用于在通式(5a)~(11a)结构上的基团R1。该化合物优选用于空穴传输或空穴注入层中。为了本发明的目的,空穴注入层是直接与阳极邻接的层。为了本发明的目的,空穴传输层是位于空穴注入层和发光层之间的层。如果根据本发明的化合物用作空穴传输或空穴注入材料,它们可以优选用电子受体化合物掺杂,例如用F4-TCNQ,或用如EP 1476881或EP 1596445中描述的化合物。
在本发明的又一其它实施方式中,通式(1)~(16)和(5a)~(11a)的化合物用作电子传输材料。此处优选一个或多个取代基R1包含至少一个单元C=O、P(=O)和/或SO2。这些基团特别优选直接结合至根据本发明的中心单元,而且特别优选还包含一个,或在氧化膦情况下包含两个其它的芳烃取代基。这特别适用于在通式(5a)~(11a)结构上的基团R1。还优选该化合物用电子供体化合物掺杂。
同样在聚合物中,通式(1)~(16)和(5a)~(11a)的重复单元能够或者用作聚合物骨架,或者用作发光单元,空穴传输单元和/或电子传输单元。此处优选的取代方式对应于上面描述的那些。
进一步优选的有机电致发光器件,特征在于通过升华方法涂覆一层或多层,其中在真空升华设备中,在低于10-5毫巴,优选低于10-6毫巴,特别优选低于10-7毫巴的压力下气相沉积所述材料。
同样优选的有机电致发光器件,特征在于通过OVPD(有机气相沉积)方法或者通过载气升华的辅助下,涂覆一层或多层,其中在10-5毫巴与1巴之间压力下施用所述材料。
还优选的有机电致发光器件,特征在于自溶液比如通过旋涂产生一层或多层,或者通过任何希望的印刷方法,比如丝网印刷、柔性版印刷或者胶板印刷产生一层或多层,但是特别优选LITI(光引发热敏成像,热转移印刷)或者喷墨印刷。对于本目的,可溶性化合物是必需的。通过该化合物的适当取代实现高的溶解度。
在用于有机电致发光器件中时,根据本发明的化合物相对于现有技术具有以下令人惊讶的优点:
1.根据本发明的化合物与根据现有技术通常使用的化合物相比,具有较低的LUMO(最低空分子轨道),因此容易还原。这导致电子注入的改进,以及因此工作电压的降低。
2.根据本发明的化合物具有小的能带间距,因此被认为是双极性结构,该结构不仅能良好地还原而且能良好地氧化。因此,它们相同地适合于空穴注入和电子注入。因而,这些化合物是在仅包含一种纯物质的发光层方向上的一个台阶。这代表器件制造中的技术的简化。
3.在有机电致发光器件中的用途上,与现有技术相比,根据本发明的化合物导致显著改进的寿命。
4.根据本发明的化合物具有非常高的热稳定性,有利于直接体相升华以纯化化合物,而且有利于在制造有机电致发光器件期间,化合物没有分解的热气相沉积。
本发明申请文本涉及根据本发明的化合物在OLEDs和PLEDs以及相应显示器中的用途。尽管描述是有限的,但对于本领域普通技术人员而言,不需要另外创造性的劳动,有可能将根据本发明的化合物也用于其它的电子器件,例如有机场效应晶体管(O-FETs),有机薄膜晶体管(O-TFTs),有机发光晶体管(O-LETs),有机集成电路(O-ICs),有机太阳能电池(O-SCs),有机场猝熄器件(O-FQDs),发光电化学电池(LECs),有机激光二极管(O-lasers),或者有机光感受器。
本发明同样涉及根据本发明的化合物在相应器件中的用途和这些器件本身。
通过以下实施例更详细地阐明本发明,而不希望将本发明限制于此。
实施例:
除非另外指出,以下合成在保护性气氛下进行。原料购买自ALDRICH或ABCR。
实施例1:3,8-双(N,N-二苯基胺)-1,2,6,7-二苯并-6,6,12,12-四甲基-6,12-二氢茚并[1,2-b]芴的合成
a)2,5-二萘-1-基对苯二甲酸二乙酯
将193.3g(0.82mol)的萘硼酸,180.4g(474mmol)的二溴对苯二甲酸二乙酯和315.9g(2.29mol)的碳酸钾首先引入850ml甲苯和850ml水的混合物中,用N2饱和30分钟。在加入1.36g(1.18mmol)的Pd(PPh3)4之后,在沸点加热该混合物4小时。冷却到室温之后,加入400ml的乙醇,将该混合物冷却到室温,并搅拌1h,抽滤沉淀,用水、乙醇和庚烷洗涤,在80℃在真空中干燥。无色固体产量为160.7g(71%)。
b)2-[4-(1-羟基-1-甲基乙基)-2,5-二萘-1-基苯基]丙-2-醇
将64.6g(136.4mmol)的2,5-二萘-1-基对苯二甲酸二乙酯首先引入600ml的THF中,将该混合物冷却到-70℃,在-70℃下于60分钟之内逐滴加入400ml(600mmol)的1.6M的甲基锂溶液。在-70℃下2h之后,首先逐滴加入30ml的冰水,然后逐滴加入60ml的50%乙酸,通过用乙酸乙酯/水萃取处理该反应混合物,有机相用Na2SO4干燥,在真空中除去溶剂,得到60.3g(99%)的无色固体。
c)1,2,6,7-二苯并-6,6,12,12-四甲基-6,12-二氢茚[1,2-b]-芴
将34.12g(76mmol)的2-[4-(1-羟基-1-甲基乙基)-2,5-二萘-1-基苯基]丙-2-醇首先引入600ml的甲苯中,加入1ml的浓H2SO4,在分水器上于沸点加热该混合物直到水被完全排出。冷却到室温之后,抽滤沉淀的反应产物(根据1H-NMR,只有两个5-元环),自NMP重结晶,得到带黄色的粉末,纯度>99.5%,产量32g(78%)。
d)3,8-二溴-1,2,6,7-二苯并-6,6,12,12-四甲基-6,12-二氢茚[1,2b]芴
将17.5g(43mmol)的1,2,6,7-二苯并-6,6,12,12-四甲基-6,12-二氢茚并[1,2-b]芴首先避光引入500ml的二氯甲烷中,冷却到5℃,在15分钟之内逐滴加入在40ml二氯甲烷中的4.7ml(86mmol)的溴,在5℃将混合物搅拌6小时。通过HPLC分析反应的等分试样监测反应。当完全转化时,通过添加20ml的乙醇结束反应,抽滤产物,用乙醇洗涤多次,随后自NMP重结晶两次,得到21.3g的淡黄色固体,根据HPLC分析,含量>99.8%。
e)3,8-双(N,N-二苯基胺)-1,2,6,7-二苯并-6,6,12,12-四甲基-6,12-二氢茚并[1,2-b]芴
将40g(70mmol)的3,8-二溴-1,2,6,7-二苯并-6,6,12,12-四甲基-6,12-二氢茚并[1,2-b]芴和31g(184mmol)的二苯胺悬浮在750ml无水甲苯中,随后加入600mg(3mmol)的三叔丁基膦和340mg(1.5mmol)的Pd(OAc)2和20g(211mmol)的叔丁醇钠,在沸点加热该反应混合物4小时。当反应完全时,加入400ml的水,抽滤固体,用乙醇洗涤,并干燥。自NMP重结晶四次,用沸腾的乙醇洗涤一次,随后二次升华(340℃,2×10-5毫巴)得到41.7g(80%)的淡黄色固体,通过HPLC确定的纯度>99.9%。
类似上述方法制备以下化合物(在升华之后得到的纯度>99.9%)(实施例2~9)。
实施例10:3,8-双(4-三苯基胺)-1,2,6,7-二苯并-6,6,12,12-四甲基-6,12-二氢茚并[1,2-b]芴的合成
将69g(122mmol)的3,8-二溴-1,2,6,7-二苯并-6,6,12,12-四甲基-6,12-二氢茚并[1,2-b]芴(来自实施例1d),115g(365mmol)的三苯基胺-4-硼酸乙二醇酯和109g(512mmol)的磷酸三钾悬浮在450ml甲苯、150ml二氧六环和600ml水的混合物中,用氮饱和该混合物,加入4.4g(14.6mmol)的三邻甲苯基膦,随后加入0.5g(2.4mmol)的乙酸钯,在沸点加热该混合物12小时。在加入500ml乙醇之后,抽滤沉淀,干燥,并自NMP重结晶五次。用沸腾的乙醇洗涤,二次升华(370℃,2x10-5毫巴)得到70g(78mmol)的二胺,纯度>99.9%(HPLC)。
类似上述方法制备以下化合物(在升华之后得到的纯度>99.9%)(实施例11~13)。
实施例14:1,2,6,7-二苯并-6,6,12,12-四-(4-叔丁基苯基)-6,12-二氢茚并[1,2-b]芴的合成
a){4-[双(4-叔丁基苯基)羟甲基]-2,5-二萘-1-基-苯基}双(4-叔丁基苯基)甲醇
将42.5g(200mmol)的叔丁基溴苯首先引入200ml的干燥THF中,将该混合物冷却到-75℃,在30分钟之内逐滴加入100ml(200mmol)的正丁基锂(在环己烷中,2M),在-75℃下搅拌该混合物另外的2小时。将21.3g(45mmol)的2,5-二萘-1-基对苯二甲酸二乙酯(如实施例1a所述制备)溶解在160ml的干燥的THF中,在-75℃下于30分钟之内逐滴加入该溶液,在-75℃下搅拌该混合物1小时,在温热到室温之后,逐滴加入20ml的50%乙酸。通过用乙酸乙酯和水萃取处理该反应混合物,用Na2SO4干燥有机相,在真空中去除溶剂,得到无色固体二醇,通过1H-NMR波谱测定的纯度>99%(40.5g,98%)。
b)1,2,6,7-二苯并-6,6,12,12-四-(4-叔丁基苯基)-6,12-二氢茚并[1,2-b]芴
将41.4g(45mmol)的{4-[双(4-叔丁基苯基)羟甲基]-2,5-二萘-1-基苯基}双(4-叔丁基苯基)甲醇悬浮在500ml的浓乙酸中,加入2ml的浓HCl,在沸点加热该混合物4小时。过滤粗产物,根据1H-NMR分析,由5,5-和6,6-环相连接的产物的混合物组成(约3:1)。通过自二氯苯重结晶七次进行分离和纯化。二次加入并通过蒸馏除去甲苯,用沸腾的正庚烷洗涤,最后二次升华(400℃,2×10-5毫巴)得到形式为无色固体的产物(16.7g,42%)。
类似实施例1和10,根据实施例14的化合物能进一步官能化。
实施例15:2,7-双(N,N-二苯基胺)-3,4,8,9-二苯并-6,6,12,12-四甲基-6,12-二氢茚并[1,2-b]芴的合成
a)2,7-双(N,N-二苯基胺)-3,4,8,9-二苯并-6,6,12,12-四甲基-6,12-二氢茚并[1,2-b]芴
类似实施例1制备该化合物,从2-萘硼酸开始而不是1-萘硼酸,通过自氯苯重结晶四次纯化,最后升华(350℃,2×10-5毫巴)。胺化的产率为66%,纯度>99.9%(HPLC)。
类似上述方法制备以下化合物(在升华之后得到的纯度>99.9%)(实施例16~23)。
实施例24:2,7-双(4-三苯基胺)-3,4,8,9-二苯并-6,6,12,12-四甲基-6,12-二氢茚并[1,2-b]芴的合成
类似实施例10制备该化合物,从2-萘硼酸开始而不是1-萘硼酸,通过自NMP重结晶四次纯化,随后升华(390℃,2×10-5毫巴)。Suzuki反应的产率为77%,纯度>99.9%(HPLC)。
类似上述方法制备以下化合物(在升华之后得到的纯度>99.9%)(实施例25~27)。
实施例28:OLEDs的制造
通过如WO 04/058911描述的一般方法制造OLEDs,在个别情况改变以匹配特定的环境(例如为实现最佳效率或色彩的层厚变化)。
在以下实施例29~47中提供各种OLEDs的结果。涂有结构化的ITO(氧化锡铟)的玻璃板形成基材。对于改进的处理,将PEDOT(自水旋涂;购买自H.C.Starck,Goslar,德国;聚(3,4-亚乙基二氧基-2,5-噻吩))直接施加到基质。OLEDs总是由以下层顺序组成:基材/PEDOT20nm/空穴注入层(HIL 1)20nm/空穴传输层(HTM 1)20nm/发光层(EML)30nm/电子传输层(ETM 1)20nm和最后是阴极。除PEDOT之外,在真空室中热气相沉积其它材料。此处的EML总是由基质材料(主体,缩写为H)和掺杂物(客体或掺杂物,缩写为D)组成,所述的掺杂物通过共蒸发与主体混合。该阴极由1nm薄的LiF层和在它上面沉积的100nm的Al层形成。表1显示所使用材料的结构。
表1:所使用材料的结构
此处ETM-1是根据现有技术的电子传输材料。ETM-2是本发明的电子传输材料。H1、H2和H3是根据现有技术的主体材料。H4是本发明的主体材料。D1是根据现有技术的掺杂物。D2、D3、D4、D5、D6和D7是根据本发明的掺杂物。
上述OLEDs通过标准方法表征;为此目的,确定电致发光光谱、效率(以cd/A测定)、作为明亮度的函数由电流/电压/亮度特性线(IUL特性线)计算的功率效率(以1m/W测定),以及和寿命。寿命定义为初始明亮度2000cd/m2下降到一半后的时间。
表2显示一些OLEDs的层结构(实施例29~47)和它们的结果。
表2:OLEDs的层结构和结果
实施例 | EML | ETL | 最大效率(cd/A) | 在1000cd/m2的电压(V) | CIE | 在2000cd/m2的寿命(h) |
29a) | H3+5%D1 | ETM1 | 6.9 | 5.8 | x=0.15/y=0.20 | 2200 |
30 | H4+5%D1 | ETM1 | 7.3 | 5.6 | x=0.15/y=0.19 | 2200 |
31 | H3+5%D1 | ETM2 | 7.5 | 5.3 | x=0.15/y=0.19 | 2600 |
32 | H1+5%D2 | ETM1 | 7.0 | 5.7 | x=0.16/y=0.20 | 2400 |
33 | H3+5%D2 | ETM1 | 7.2 | 5.3 | x=0.14/y=0.19 | 3100 |
34 | H4+5%D2 | ETM2 | 7.5 | 5.2 | x=0.14/y=0.19 | 2900 |
35 | H1+5%D3 | ETM1 | 21.4 | 5.1 | x=0.18/y=0.42 | 6300 |
36 | H2+5%D3 | ETM1 | 18.4 | 5.2 | x=0.18/y=0.43 | 7200 |
37 | H3+5%D3 | ETM1 | 20.2 | 5.3 | x=0.18/y=0.42 | 7500 |
38 | H1+5%D4 | ETM1 | 12.3 | 5.5 | x=0.15/y=0.30 | 5200 |
39 | H3+5%D4 | ETM1 | 12.7 | 5.4 | x=0.14/y=0.29 | 5300 |
40 | H3+5%D4 | ETM2 | 13.8 | 5.2 | x=0.14/y=0.29 | 5800 |
41 | H1+5%D5 | ETM1 | 9.2 | 5.6 | x=0.15/y=0.26 | 3100 |
42 | H2+5%D5 | ETM2 | 10.8 | 5.3 | x=0.14/y=0.26 | 3700 |
43 | H3+5%D5 | ETM2 | 9.9 | 5.5 | x=0.14/y=0.26 | 3800 |
44 | H1+5%D6 | ETM1 | 6.2 | 5.7 | x=0.15/y=0.14 | 2000 |
45 | H2+5%D6 | ETM1 | 6.0 | 5.6 | x=0.14/y=0.13 | 2200 |
46 | H3+5%D6 | ETM2 | 6.1 | 5.6 | x=0.14/y=0.13 | 2400 |
47 | H3+5%D7 | ETM2 | 12.6 | 5.3 | x=0.14/y=0.28 | 5900 |
a)现有技术的比较实验。
如从表2中的结果可见,根据本发明的OLEDs比根据现有技术的OLEDs(实施例29)具有更长的寿命。
Claims (12)
1.通式(5)、(8)、(11)、(12)、(13)、(14)、(15)或(16)的化合物,
其中以下应用于符号和标记:
Y每一次出现相同或不同,是CR1;
X每一次出现相同或
不同,是C(R1)2的二价桥连;
R1每一次出现相同或不同,是H,F,Cl,Br,I,N(Ar)2,C(=O)Ar,P(=O)Ar2,S(=O)Ar,S(=O)2Ar,CR2=CR2Ar,CN,NO2,Si(R2)3,B(OR2)2,OSO2R2,具有1~40个碳原子的直链烷基、烷氧基或硫代烷氧基,或具有3~40个碳原子的支链或环状烷基、烷氧基或硫代烷氧基,它们每个可被一个或多个基团R2取代,并且其中一个或多个非相邻的CH2基团可以被R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S或CONR2替代,且其中一个或多个H原子可以被F、Cl、Br、I、CN或NO2替代,或者具有5~40个芳环原子的芳香或杂芳环系,在每一情况下所述环系可以被一个或多个基团R2取代,或者具有5~40个芳环原子的芳氧基或杂芳氧基基团,它们可被一个或多个基团R2取代,或者这些体系的的组合;此处两个或多个相邻的取代基R1还可以彼此形成单或多环的脂肪或芳香环系;
Ar每一次出现相同或不同,是具有5~30个芳环原子的芳香或杂芳环系,它们可被一个或多个非芳基R1取代;此处两个在相同的氮或磷原子上的基团Ar,还可以通过单键或桥连X彼此连接;
R2每一次出现相同或不同,是H或具有1~20个碳原子的脂肪、芳香和/或杂芳烃基,其中另外H原子也可以被F替代;此处两个或多个相邻的取代基R2还可以彼此形成单或多环的脂肪或芳香环系;
以下化合物除外:
3.如权利要求1所述的化合物,其特征在于所述标记R1,每一次出现相同或不同,代表H,F,Br,C(=O)Ar,P(=O)Ar2,CR2=CR2Ar,具有1~5个碳原子的直链烷基或具有3~5个碳原子的支链烷基,其中一个或多个非相邻的CH2基团可被-R2C=CR2-、-C≡C-或-O-替代,且其中一个或多个H原子可以被F替代,或者具有6~16个碳原子的芳基或具有2~16个碳原子的杂芳基,或螺二芴基团,它们每个可被一个或多个基团R2被取代,或者这些体系两个或三个的组合,和/或特征在于至少一个符号R1代表通式(17)或(18)的基团N(Ar)2,
其中E代表单键、O、S、N(R2)或C(R2)2;
Ar1每一次出现相同或不同,是具有5~20个芳环原子的芳基或杂芳基基团,或具有15~30个芳环原子的三芳基胺基团,它们每个可被一个或多个基团R2取代;
P每一次出现相同或不同,是0或者1。
4.如权利要求1所述的化合物,其特征在于包含在桥连X中的基团R1相同或不同,选自H,具有1~5个碳原子的直链烷基或具有3~5个碳原子的支链烷基,其中一个或多个非相邻的CH2基团可被-R2C=CR2-、-C≡C-或-O-替代,且其中一个或多个H原子可被F替代,或者具有6~16个碳原子的芳基或具有2~16个碳原子的杂芳基,它们的每个可被一个或多个基团R2取代,或者这些体系的两个或三个的组合;此处两个结合至相同桥原子的基团R1还可以彼此形成环系。
5.包括一种或多种如权利要求1~4任一项所述化合物的聚合物或低聚物,其特征在于一个或多个基团R1代表至聚合物或低聚物的结合。
6.包括一种或多种如权利要求1~4任一项所述化合物的树枝状高分子,其特征在于一个或多个基团R1代表至所述树枝状高分子的结合。
7.制备如权利要求1~4任一项所述化合物的方法,其包括如下步骤:
a)将官能化的萘与四官能化的苯衍生物偶联;
b)利用酸催化闭环;以及
c)通过步骤a)和b)得到的母体结构通过溴化而官能化,随后通过Hartwig-Buchwald偶联至芳香胺,或通过Suzuki偶联至芳基硼酸或芳基硼酸衍生物。
8.如权利要求1~6任一项所述化合物在有机电子器件中的用途。
9.一种有机电子器件,其包括阳极,阴极和至少一层有机层,所述有机层包括至少一种如权利要求1~6任一项所述的化合物。
10.如权利要求9所述的有机电子器件,选自有机电致发光器件、有机场影响晶体管、有机薄膜晶体管、有机发光晶体管、有机集成电路、有机太阳能电池、有机场猝熄器件、发光电化学电池、有机激光器二极管和有机光感受器。
11.如权利要求10所述的有机电子器件,其选自有机电致发光器件,其包括阴极、阳极、一层或多层发光层以及任选的其它层,所述其它层选自空穴注入层、空穴传输层、电子传输层、电子注入层和/或电荷产生层。
12.如权利要求11所述的有机电子器件,其特征在于一个或多个取代基R1选自简单或稠合的芳基或杂芳基,并且如权利要求1~4任一项所述的化合物用作用于荧光掺杂物的主体,和/或特征在于一个或多个取代基R1和/或桥连X包含至少一个基团C=O、P(=O)和/或SO2,并且如权利要求1~4任一项所述的化合物用作用于磷光掺杂物的基质,和/或特征在于一个或多个取代基R1包含至少一个乙烯基芳基单元、至少一个乙烯基芳胺单元和/或至少一个芳基胺单元,并且如权利要求1~4任一项所述的化合物用作发光材料,和/或特征在于一个或多个取代基R1代表基团N(Ar)2,并且如权利要求1~4任一项所述的化合物任选用电子受体化合物掺杂,和特征在于它用作空穴传输材料或空穴注入材料,和/或特征在于一个或多个取代基R1包含至少一个单元C=O、P(=O)和/或SO2,并且如权利要求1~4任一项所述的化合物可以任选用电子供体化合物掺杂,并用作电子传输材料。
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WO2024132993A1 (de) | 2022-12-19 | 2024-06-27 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2024132892A1 (en) | 2022-12-19 | 2024-06-27 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2024133048A1 (en) | 2022-12-20 | 2024-06-27 | Merck Patent Gmbh | Method for preparing deuterated aromatic compounds |
WO2024170609A1 (en) | 2023-02-17 | 2024-08-22 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2024170605A1 (en) | 2023-02-17 | 2024-08-22 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
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CN1606393A (zh) * | 2003-09-30 | 2005-04-13 | 三洋电机株式会社 | 有机电致发光元件 |
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US5942340A (en) * | 1997-10-02 | 1999-08-24 | Xerox Corporation | Indolocarbazole electroluminescent devices |
JP4996794B2 (ja) | 2000-08-10 | 2012-08-08 | 三井化学株式会社 | 炭化水素化合物、有機電界発光素子用材料および有機電界発光素子 |
EP1217668A1 (de) * | 2000-12-22 | 2002-06-26 | Covion Organic Semiconductors GmbH | Verwendung von Bor- und Aluminium-Verbindungen in Elektronik-Bauteilen |
KR100578424B1 (ko) * | 2002-05-07 | 2006-05-11 | 주식회사 엘지화학 | 새로운 유기 발광용 화합물 및 이를 이용한 유기 발광 소자 |
JP2004075567A (ja) | 2002-08-12 | 2004-03-11 | Idemitsu Kosan Co Ltd | オリゴアリーレン誘導体及びそれを利用した有機エレクトロルミネッセンス素子 |
US6849348B2 (en) | 2002-12-31 | 2005-02-01 | Eastman Kodak Company | Complex fluorene-containing compounds |
TWI278503B (en) * | 2003-01-21 | 2007-04-11 | Univ Nat Taiwan | Pyrimidine containing di-fluorene oligomer for OLED |
JP4810830B2 (ja) * | 2004-01-15 | 2011-11-09 | 東ソー株式会社 | フルオレン基を母核とするアミン化合物並びにその製造方法及び用途 |
JP4065547B2 (ja) * | 2004-04-12 | 2008-03-26 | キヤノン株式会社 | フルオレン化合物及びそれを用いた有機発光素子 |
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- 2007-05-03 US US12/303,200 patent/US8932732B2/en active Active
- 2007-05-03 KR KR1020087032190A patent/KR101465270B1/ko active IP Right Grant
- 2007-05-03 AT AT07724812T patent/ATE549306T1/de active
- 2007-05-03 EP EP07724812A patent/EP2024310B1/de active Active
- 2007-05-03 WO PCT/EP2007/003886 patent/WO2007140847A1/de active Application Filing
- 2007-05-03 JP JP2009512440A patent/JP5518472B2/ja active Active
- 2007-05-03 CN CN200780020514.1A patent/CN101460434B/zh active Active
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TW200815313A (en) | 2008-04-01 |
DE102006025846A1 (de) | 2007-12-06 |
KR101465270B1 (ko) | 2014-11-26 |
ATE549306T1 (de) | 2012-03-15 |
JP2009538839A (ja) | 2009-11-12 |
EP2024310A1 (de) | 2009-02-18 |
US20090184313A1 (en) | 2009-07-23 |
EP2024310B1 (de) | 2012-03-14 |
WO2007140847A1 (de) | 2007-12-13 |
CN101460434A (zh) | 2009-06-17 |
KR20090024756A (ko) | 2009-03-09 |
US8932732B2 (en) | 2015-01-13 |
JP5518472B2 (ja) | 2014-06-11 |
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