CN110759835B - 苝醌类有机化合物及其应用 - Google Patents
苝醌类有机化合物及其应用 Download PDFInfo
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- CN110759835B CN110759835B CN201911036703.9A CN201911036703A CN110759835B CN 110759835 B CN110759835 B CN 110759835B CN 201911036703 A CN201911036703 A CN 201911036703A CN 110759835 B CN110759835 B CN 110759835B
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- 239000000203 mixture Substances 0.000 claims description 53
- 150000002894 organic compounds Chemical class 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 230000000903 blocking effect Effects 0.000 claims description 17
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- IYYMDGDZPDXTGT-UHFFFAOYSA-N perylene-1,2-dione Chemical compound C1=CC(C2=C3C(=CC(C2=O)=O)C=CC=C32)=C3C2=CC=CC3=C1 IYYMDGDZPDXTGT-UHFFFAOYSA-N 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
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- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 7
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/01—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to acyclic carbon atoms
- C07C205/03—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C207/00—Compounds containing nitroso groups bound to a carbon skeleton
- C07C207/02—Compounds containing nitroso groups bound to a carbon skeleton the carbon skeleton not being further substituted
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
- C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/24—Halogenated aromatic hydrocarbons with unsaturated side chains
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/20—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups being part of rings other than six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/31—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/35—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C255/47—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of rings being part of condensed ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/52—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of six-membered aromatic rings being part of condensed ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
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Abstract
本发明涉及一种如通式(I)或(II)所示的苝醌类有机化合物及其应用。所述苝醌类有机化合物,具有优异的空穴传输性质及稳定性,可作为有机电致发光元件中的空穴注入层材料,也可以作为掺杂剂掺杂在空穴注入层或空穴传输层中,这样既可用低电压驱动,也可提高电致发光效率,延长器件寿命。
Description
本申请要求于2018年12月06日提交中国专利局、申请号为2018114854373发明名称为“一种苝醌类有机化合物及其应用”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,特别是涉及苝醌类有机化合物及其应用。
背景技术
由于有机发光二极管(OLED)具有种类多、制造成本低、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。
有机发光二极管是由正极与负极以及在它们中间的有机物层三部分组成。为了提高有机发光二极管的效率与寿命,有机物层一般具有多层结构,每一层包含有不同的有机物质。具体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。这种有机发光二极管发光的基本原理为:当在两个电极之间施加电压时,正极向有机层注入空穴,负极向有机层注入电子,注入的空穴与电子相遇时会成激子,该激子跃迁回基态时发光。这种有机发光二极管具有自发光、高亮度、高效率、低驱动电压、广视角、高对比度、高响应性等优点。为了提高注入的空穴和电子的复合效率,需要进一步对有机发光二极管的结构和材料等方面进行改良。
所以有科学家利用芳香族二胺衍生物(专利CN104718636A)或芳香族稠环二胺衍生物(专利CN107922312A)作为有机发光二极管的空穴传输材料,以此来提高注入空穴的效率,但这时需要提高使用电压才可以使有机发光二极管充分发光,这就导致了有机发光二极管寿命降低和消耗电量增大的问题。
最近在有机发光二极管的空穴传输层中掺杂电子受体是解决此类问题的新方法,例如四氰基醌二甲烷(TCNQ)或2,3,5,6-四氟-四氰基-1,4-苯并醌二甲烷(F4TCNQ)(Chemical Science 2018,9(19),4468-4476;Appl.Phys.Lett.,2018,112(8),083303/1-083303/2;Chemistry of Materials 2018,30(3),998-1010),然而,这些化合物在用于掺杂有机层时存在诸多缺陷,例如:在有机发光二极管的制作工序中操作不稳定,在有机发光二极管驱动时稳定性不足,寿命下降,或在用真空蒸镀来制造有机发光二极管时,上述化合物会在装置内扩散,污染装置。
目前,仍需进一步改进空穴传输层中掺杂的电子受体,即P-dopant型掺杂剂,特别是需要一种可以实现有机发光二极管低电压化和长寿命化的掺杂剂。
发明内容
鉴于上述现有技术的不足,本发明的目的是提供一种苝醌类有机化合物及其应用。
本发明的技术方案如下:
一种如通式(I)或(II)所示的苝醌类有机化合物:
其中,
X每次出现分别独立选自CR1,N,CR1R2,NR1,C=O,C=NR1,C=CR1R2,C=Ar2,SiR1R2,PR1,O,S,C=SO2或SO2,且至少一个X选自C=O,C=NR1,SO2,C=CR1R2,C=Ar2或C=SO2;
Y选自C或者N或者P;
R1-R2每次出现分别独立选自H、D,碳原子数1~20的直链烷基、烷氧基或硫代烷氧基,或碳原子数3~20的支链或环状的烷基、烷氧基、硫代烷氧基、甲硅烷基,或取代的碳原子数1~20的酮基,或碳原子数2~20的烷氧基羰基,或碳原子数7~20的芳氧基羰基,或氰基,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,亚硝基,CF3,Cl,Br,F,I,可交联的基团,或取代或未取代的碳原子数5~40的芳香基或杂芳香基,或碳原子数5~40的芳氧基或杂芳氧基,或这些基团的组合,两个或者多个相邻的R1和/或两个或多个相邻的R2可任选地彼此形成脂族、芳族或杂芳族环系;
Ar0-Ar2每次出现分别独立选自取代或未取代的环原子数4~40的芳香基团、杂芳香基团、芳氧基基团、杂芳氧基基团或非芳香环系,或这些基团的组合,其中一个或多个基团彼此和/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;
当所述Ar0和Ar1均为环原子数为6的芳香基团,且至少有1个X选自C=CR1R2时,所述R1和R2不同时为H。
一种混合物,所述混合物,包含有至少一种上述的苝醌类有机化合物,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,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,主体材料或有机染料。
一种组合物,所述组合物包含上述的苝醌类有机化合物,及有机溶剂。
一种有机电子器件,所述有机电子器件包含上述的苝醌类有机化合物,或上述的混合物,或上述的组合物。
与现有方案相比,本发明具有以下有益效果:
上述苝醌类有机化合物,具有优异的空穴传输性质及稳定性,可作为有机电致发光元件中的空穴注入层材料,也可以作为掺杂剂掺杂在空穴注入层或空穴传输层中,这样既可用低电压驱动,也可提高电致发光效率,延长器件寿命。
附图说明
图1是本发明的发光器件结构图,图中101是基板,102是阳极,103是空穴注入层(HIL),104是空穴传输层(HTL),105是发光层,106是电子注入层(EIL)或电子传输层(ETL),107是阴极。
具体实施方式
为了便于理解本发明,下面将结合相关附图对本发明进行更全面的描述。附图中给出了本发明的较佳实施例。但是,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例。相反地,提供这些实施例的目的是使对本发明的公开内容的理解更加透彻全面。
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。
本发明所述化合物中,当任何变量(例如R1、R2等)在任何组分中出现超过一次,则其每次出现的定义独立于其它每次出现的定义。同样,允许取代基及变量的组合,只要这种组合使化合物稳定。
在本发明中,组合物、印刷油墨、油墨、和墨水具有相同的含义,可以互换。
在本发明中,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。
在本发明中,金属有机络合物,金属有机配合物,有机金属配合物具有相同的含义,可以互换。
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。
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。
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。以下对这些能级的确定做一介绍。
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 03W(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。
一种如通式(I)或(II)所示的苝醌类有机化合物:
其中,
X每次出现分别独立选自CR1,N,CR1R2,NR1,C=O,C=NR1,C=CR1R2,C=Ar2,SiR1R2,PR1,O,S,C=SO2或SO2,且至少一个X选自C=O,C=NR1,SO2,C=CR1R2,C=Ar2或C=SO2;
Y选自C或者N或者P;
R1-R2每次出现分别独立选自H、D,碳原子数1~20的直链烷基、烷氧基或硫代烷氧基,或碳原子数3~20的支链或环状的烷基、烷氧基、硫代烷氧基、甲硅烷基,或取代的碳原子数1~20的酮基,或碳原子数2~20的烷氧基羰基,或碳原子数7~20的芳氧基羰基,或氰基,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,亚硝基,CF3,Cl,Br,F,I,可交联的基团,或取代或未取代的碳原子数5~40的芳香基或杂芳香基,或碳原子数5~40的芳氧基或杂芳氧基,或这些基团的组合,两个或者多个相邻的R1和/或两个或多个相邻的R2可任选地彼此形成脂族、芳族或杂芳族环系;
Ar0-Ar2每次出现分别独立选自取代或未取代的环原子数4~40的芳香基团、杂芳香基团、芳氧基基团、杂芳氧基基团或非芳香环系,或这些基团的组合,其中一个或多个基团彼此和/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;
当所述Ar0和Ar1均为环原子数为6的芳香基团,且至少有1个X选自C=CR1R2时,所述R1和R2不同时为H。
进一步地,R1-R2每次出现分别独立选自D,碳原子数1~10的直链烷基、烷氧基或硫代烷氧基,或碳原子数3~10的支链或环状的烷基、烷氧基、硫代烷氧基、甲硅烷基,或取代的碳原子数1~10的酮基,或碳原子数2~10的烷氧基羰基,或碳原子数7~10的芳氧基羰基,或氰基,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,亚硝基,CF3,Cl,Br,F,I,或取代或未取代的碳原子数5~20的芳香基或杂芳香基,或碳原子数5~20的芳氧基或杂芳氧基,或这些基团的组合,其中一个或多个基团彼此和/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。
在某个优选地实施例中,R1-R2多次出现时,至少一个选自硝基,亚硝基,CF3,Cl,Br,F,I,氰基,或被硝基,亚硝基,CF3,Cl,Br,F,I,氰基取代的芳香基或杂芳香基。
在某个优选地实施例中,R1-R2多次出现时,至少一个选自直链或支链烷基。
在某个优选地实施例中,R1-R2多次出现时,至少一个选自芳香基或杂芳香基;更优选地,选自苯、奈、菲、螺环、三嗪、苯并菲、咔唑、呋喃及其衍生物。
在一些优选的实施例中,至少有1个X选自G1-G27中的一种:
所述E每次出现分别独立选自CR3R4,NR3,O,S或SO2;
R3-R4每次出现分别独立选自H、D,碳原子数1~20的直链烷基、烷氧基或硫代烷氧基,或碳原子数3~20的支链或环状的烷基、烷氧基、硫代烷氧基、甲硅烷基,或取代的碳原子数1~20的酮基,或碳原子数2~20的烷氧基羰基,或碳原子数7~20的芳氧基羰基,或氰基,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,亚硝基,CF3,Cl,Br,F,I,可交联的基团,或取代或未取代的碳原子数5~40的芳香基或杂芳香基,或碳原子数5~40的芳氧基或杂芳氧基,或这些基团的组合,两个或者多个相邻的R3可任选地彼此形成脂族、芳族或杂芳族环系。
进一步地,R3-R4每次出现分别独立选自D,碳原子数1~10的直链烷基、烷氧基或硫代烷氧基,或碳原子数3~10的支链或环状的烷基、烷氧基、硫代烷氧基、甲硅烷基,或取代的碳原子数1~10的酮基,或碳原子数2~10的烷氧基羰基,或碳原子数7~10的芳氧基羰基,或氰基,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,亚硝基,CF3,Cl,Br,F,I,或取代或未取代的碳原子数5~20的芳香基或杂芳香基,或碳原子数5~20的芳氧基或杂芳氧基,或这些基团的组合,两个或者多个相邻的R1和/或两个或多个相邻的R2可任选地彼此形成脂族、芳族或杂芳族环系。
在一优选地实施例中,至少有2个X选自C=O,C=NR1,SO2,C=CR1R2,C=Ar2或C=SO2;在一优选地实施例中,至少有3个X选自C=O,C=NR1,SO2,C=CR1R2,C=Ar2或C=SO2;在一优选地实施例中,至少有4个X选自C=O,C=NR1,SO2,C=CR1R2,C=Ar2或C=SO2;更优选地,至少有4个X选自C=O,C=NR1,C=CR1R2或C=Ar2。
在一优选地实施例中,至少一个X选自C=CR1R2;在一优选地实施例中,至少两个X选自C=CR1R2;在一优选地实施例中,至少3个X选自C=CR1R2;在一优选地实施例中,至少4个X选自C=CR1R2;优选地,R1-R2多次出现时,至少一个选自硝基,亚硝基,CF3,Cl,Br,F,I,氰基,或被硝基,亚硝基,CF3,Cl,Br,F,I,氰基取代的芳香基或杂芳香基;更优选地,R1-R2多次出现时,均选自硝基,亚硝基,CF3,Cl,Br,F,I,氰基,或被硝基,亚硝基,CF3,Cl,Br,F,I,氰基取代的芳香基或杂芳香基。
具体地,C=CR1R2优选自以下基团中的一种:
在一优选地实施例中,至少一个X选自C=Ar2;在一优选地实施例中,至少两个X选自C=Ar2;在一优选地实施例中,至少3个X选自C=Ar2;在一优选地实施例中,至少4个X选自C=Ar2;具体地,C=Ar2优选自以下基团中的一种:
在一优选地实施例中,至少一个X选自C=NR1;在一优选地实施例中,至少两个X选自C=NR1;在一优选地实施例中,至少3个X选自C=NR1;在一优选地实施例中,至少4个X选自C=NR1。
进一步的,Ar0-Ar2每次出现分别独立选自取代或未取代的环原子数4~30的芳香基团、杂芳香基团、芳氧基基团、杂芳氧基基团或非芳香环系,或这些基团的组合,其中一个或多个基团彼此和/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;
进一步的,Ar0-Ar2每次出现分别独立选自取代或未取代的环原子数4~20的芳香基团、杂芳香基团、芳氧基基团、杂芳氧基基团或非芳香环系,或这些基团的组合,其中一个或多个基团彼此和/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。
进一步地,Ar0-Ar2每次出现分别独立选自取代或未取代的环原子数4~15的芳香基团、杂芳香基团、芳氧基基团、杂芳氧基基团或非芳香环系,或这些基团的组合,其中一个或多个基团彼此和/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。
在一些优选的实施例中,所述Ar0-Ar1每次出现分别独立包含以下基团:
其中:
X1每次出现分别独立选自N或CR3;
Y1每次出现分别独立选自NR3,CR3R4,SiR3R4,O、S或PR3;
R3-R4含义同上所述。
在某个优选地实施例中,R3-R4多次出现时,至少一个选自硝基,亚硝基,CF3,Cl,Br,F,I,氰基,或被硝基,亚硝基,CF3,Cl,Br,F,I,氰基取代的芳香基或杂芳香基。
在某个优选地实施例中,R3-R4多次出现时,至少一个选自直链或支链烷基。
在某个优选地实施例中,R3-R4多次出现时,至少一个选自芳香基或杂芳香基;更优选地,选自苯、奈、菲、螺环、三嗪、苯并菲、咔唑、呋喃及其衍生物。
在某个优选地实施例中,R3-R4多次出现时,至少一个选自硝基,亚硝基,CF3,Cl,Br,F,I,氰基,或被硝基,亚硝基,CF3,Cl,Br,F,I,氰基取代的芳香基或杂芳香基。
在某个优选地实施例中,R3-R4多次出现时,至少一个选自直链或支链烷基。
在某个优选地实施例中,R3-R4多次出现时,至少一个选自芳香基或杂芳香基;更优选地,选自苯、奈、菲、螺环、三嗪、苯并菲、咔唑、呋喃及其衍生物。
进一步地,所述Ar0-Ar1每次出现分别独立选自如下结构基团中的一种或它们的组合:
其中:环上的H原子可以进一步被取代。
进一步地,所述Ar0-Ar1每次出现分别独立选自苯、联苯、萘、蒽、菲、苯并菲、芘、苝、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、吡嗪或噁二唑及其衍生物。
在一优选地实施例中,所述通式(I)选自通式(2-1)-(2-4)中的任意一种:
在一优选地实施例中,所述通式(I)和(II)分别独立选自通式(3-1)-(3-5)中的任意一种:
优选地,X每次出现分别独立选自CR1或N。
在一个优选地实施例中,通式(3-2)中Y1每次出现时选自相同的基团;在一个优选地实施例中,通式(3-2)中Y1每次出现时选自不同的基团。
可以理解地,上述苝醌类有机化合物的LUMO能级低于-5.3eV;更优选地,LUMO能级低于-5.4eV;更优选地,LUMO能级低于-5.5eV。
在本发明中,“芳香基团”指至少包含一个芳环的烃基,包括单环基团和多环的环系统。“杂芳香基团”指包含至少一个芳杂环的烃基(含有杂原子),包括单环基团和多环的环系统。这些多环的环可以具有两个或多个环,其中两个碳原子被两个相邻的环共用,即稠环。多环的这些环种,至少一个是芳香族的或芳杂族的。对于本发明的目的,芳香族或芳杂族环系不仅包括芳香基或芳杂基的体系,而且,其中多个芳香基或芳杂基也可以被短的非芳族单元间断(如C、N、O、Si、S或P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。
具体地,芳香基团的例子有:苯、萘、蒽、菲、二萘嵌苯、并四苯、芘、苯并芘、三亚苯、苊、芴、及其衍生物。
具体地,杂芳香基团的例子有:呋喃、苯并呋喃、噻吩、苯并噻吩、吡咯、吡唑、三唑、咪唑、噁唑、噁二唑、噻唑、四唑、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、吡啶、吡嗪、哒嗪、嘧啶、三嗪、喹啉、异喹啉、邻二氮萘、喹喔啉、菲啶、伯啶、喹唑啉、喹唑啉酮、及其衍生物。
在一些实施例中有机化合物的结构如下所示,但不仅限于此:
本发明还涉及所述组合物作为有机铁磁材料,铁磁性有机化合物是指具有铁磁性的有机材料,又称有机铁磁材料,传统铁磁材料都是含铁族或稀土族金属元素的合金和氧化物等无机材料,其强磁性源于原子磁矩,是由电子轨道磁矩和电子自旋磁矩两部分组成,这些无机磁性材料有密度大、加工成型困难等缺陷,在本发明的苝醌类有机化合物其自由基阴离子盐或二阴离子盐中,LUMO能级低,基态稳定,并且存在稳定的未满电子层,可以提供稳定的磁矩源,因此表现为磁性,可应用在铁磁材料中(具体可参照文献Angew.Chem.Int.Ed.Engl.1994,33.385-415)。
下面列出可作为有机铁磁材料的例子:
[M Cp2 *]n+[DPA-k]m-,[M]n+[DPA-k]m-,[M TPP]n+[DPA-k]m-,[M1 M2]n+[DPA-k]m-
M是一金属,有大于40的原子量;M1是一金属,有大于40的原子量;M2是一金属,有大于40的原子量;Cp2 *是二环戊二烯基;TPP是三苯基膦;m,n是一整数,其值从1到此金属的最大配位数。
DPA-k为上述实施例中有机化合物结构,k为编号。
在一些优选的实施例中,有机铁磁材料选自[FeIII Cp2 *]+[DPA-1]-,[CrIII Cp2 *]+[DPA-1]-,[Mn TPP]+[DPA-1]-,[V]+[DPA-1]-,[FeIII Cp2 *]+[DPA-2]-,[CrIII Cp2 *]+[DPA-2]-,[Mn TPP]+[DPA-2]-,[V]+[DPA-2]-。
按照发明的有机化合物,可以作为功能材料用于电子器件的功能层中。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。
在一个特别优选的实施例中,按照本发明的有机化合物用于空穴注入层(HIL)或空穴传输层(HTL)中。
在一个非常优选的实施例中,按照本发明的有机化合物做为p型参杂材料用于空穴注入层(HIL)或空穴传输层(HTL)中。
在某些实施例中,按照发明的有机化合物,其T1≥0.3eV,较好是≥0.6eV,最好是≥0.8eV。
功能材料需要好的热稳定性。一般的,按照本发明的有机化合物,其玻璃化温度Tg≥100℃,在一个优选的实施例中,Tg≥120℃,在一个较为优选的实施例中,Tg≥140℃,在一个更为优选的实施例中,Tg≥160℃,在一个最为优选的实施例中,Tg≥180℃。
在某些优先的实施例中,按照本发明的有机化合物,其((HOMO-(HOMO-1))≥0.2eV,较好是≥0.25eV,更好是≥0.3eV,更更好是≥0.35eV,非常好是≥0.4eV,最好是≥0.45eV。
本发明还提供一种混合物,其特征在于,包含有至少一种以上所述的有机化合物,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WO 2011110277A1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。
在一些优选的实施例中,所述混合物,其中所述的另一种有机功能材料选于空穴注入材料(HIM),空穴传输材料(HTM),和主体材料(Host)。
在某些优先的实施例中,所述混合物,其中所述的有机化合物的LUMO要等于或低于另一种有机功能材料的HOMO+0.2eV。
在某些较为优先的实施例中,所述混合物,其中所述的有机化合物的LUMO要等于或低于另一种有机功能材料的HOMO+0.1eV。
在某些特别优先的实施例中,所述混合物,其中所述的有机化合物的LUMO要等于或低于另一种有机功能材料的HOMO。
在其中一个实施例中,所述混合物包括至少一种空穴注入材料(HIM)或空穴传输材料和一种掺杂剂,所述掺杂剂是上述的苝醌类有机化合物,所述掺杂剂与主体的摩尔比是1:1至1:100000。
下面对HIM/HTM/EBM,和Host(主体材料)作一些较详细的描述(但不限于此)。
1.HIM/HTM/EBM
合适的有机HIM/HTM材料可选包含有如下结构单元的化合物:酞菁、卟啉、胺、芳香胺、联苯类三芳胺、噻吩、并噻吩、吡咯、苯胺、咔唑、氮茚并氮芴及它们的衍生物。另外,合适的HIM也包括含有氟烃的聚合物、含有导电掺杂的聚合物、导电聚合物,如PEDOT/PSS;自组装单体,如含有膦酸和sliane衍生物的化合物;金属氧化物,如MoOx;金属络合物和交联化合物等。
电子阻挡层(EBL)用来阻挡来自相邻功能层,特别是发光层的电子。对比一个没有阻挡层的发光器件,EBL的存在通常会导致发光效率的提高。电子阻挡层(EBL)的电子阻挡材料(EBM)需要有比相邻功能层,如发光层更高的LUMO。在一个优先的实施方案中,EBM有比相邻发光层更大的激发态能级,如单重态或三重态,取决于发光体,同时,EBM有空穴传输功能。通常具有高的LUMO能级的HIM/HTM材料可以作为EBM。
可用作HIM,HTM或EBM的环芳香胺衍生化合物的例子包括(但不限于)如下的一般结构:
每个Ar1~Ar9可独立选自环芳香烃化合物,如苯、联苯、三苯基、苯并、萘、蒽、非那烯、菲、芴、芘、屈、苝、薁;芳香杂环化合物,如二苯并噻吩、二苯并呋喃、呋喃、噻吩、苯并呋喃、苯并噻吩、咔唑、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、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、二苯并硒吩、苯并硒吩、苯并呋喃吡啶、吲哚咔唑、吡啶吲哚、吡咯二吡啶、呋喃二吡啶、苯并噻吩吡啶、噻吩吡啶、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。其中,Ar1~Ar9可以进一步被取代,取代基可选为氢、氘、烷基、烷氧基、氨基、烯、炔、芳烷基、杂烷基、芳基和杂芳基。
在一个方面,Ar1~Ar9可独立选自包含如下结构单元的基团:
Y0每次出现时,独立选自C(R)2或NR或O或S,X0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。
环芳香胺衍生化合物的另外的例子可参见US3567450,US4720432,US5061569,US3615404,和US5061569。
可用作HTM或HIM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,有大于40的原子量;
(Y1-Y2)是一两齿配体,Y1和Y2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。
在一个实施例中,(Y1-Y2)是2-苯基吡啶衍生物。
在另一个实施例中,(Y1-Y2)是一卡宾配体。
在另一个实施例中,M选于Ir、Pt、Os和Zn。
在另一个实施例中,金属络合物的HOMO大于-5.5eV(相对于真空能级)。
在下面的表中列出合适的可作为HIM/HTM/EBM化合物的例子:
2.三重态主体材料(Triplet Host):
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;(Y3-Y4)是一两齿配体,Y3和Y4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:X0,Y0含义同上,Ar10~Ar30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:
本发明的一个目的是为蒸镀型OLED提供材料解决方案。
在某些实施例中,按照本发明的金属配合物,其分子量≤1200g/mol,优选≤1100g/mol,很优选≤1000g/mol,更优选≤950g/mol,最优选≤900g/mol。
本发明的另一个目的是为印刷OLED提供材料解决方案。
在某些实施例中,按照本发明的金属配合物,其分子量≥800g/mol,优选≥900g/mol,很优选≥1000g/mol,更优选≥1100g/mol,最优选≥1200g/mol。
在另一些实施例中,按照本发明的金属配合物,在25℃时,在甲苯中的溶解度≥2mg/ml,优选≥3mg/ml,更优选≥4mg/ml,最优选≥5mg/ml。
本发明还涉及一种组合物,包含至少一种如上所述的苝醌类有机化合物或高聚物或混合物,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,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,包含至少一种如上所述的有机金属配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≥275℃或≥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0.01至10wt%的按照本发明的苝醌类有机化合物或高聚物或混合物,较好的是0.1至15wt%,更好的是0.2至5wt%,最好的是0.25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,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 andProduction Methods),ISBN 3-540-67326-1。
本发明还提供一种如上所述的苝醌类有机化合物、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,优选将所述有机化合物用于OLED器件的空穴注入或传输层。
本发明进一步涉及一种有机电子器件,至少包含一种如上所述的苝醌类有机化合物、或混合物。一般地,此种有机电子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有机化合物。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 Emitting Diode)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。
在某些特别优先的实施例中,所述的电致发光器件,其空穴注入或传输层包含一种如上所述的有机化合物或混合物。
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。
进一步的,所述的有机电子器件为有机发光二极管(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 Emitting Diode)。
在其中一个实施例中,本发明是一种有机磁铁,所述磁铁包括上述的苝醌类有机化合物或者其自由基阴离子盐或二阴离子盐。
在其中一个实施例中,本发明是一种有机半导体,所述导体包括上述的苝醌类有机化合物或其自由基阴离子盐或二阴离子盐。
下面对本发明的苝醌类有机化合物用于空穴传输带区域的层中时(空穴注入层或空穴传输层),作一些较详细的描述(但不限于此)。
接着,对本发明的有机电子器件进行说明。
本发明的苝醌类有机化合物在阳极和阴极之间具有包括发光层的一层或多层的有机薄膜层。并且,形成有机薄膜层的至少一层含有本发明的苝醌类有机化合物。
如说明书附图1所示,有机电子器件中,在基板(101)上一次层叠阳极(102)、空穴注入层(HIL)(103)、空穴传输层(HTL)(104)、发光层(105)、电子阻挡层(EBL)、电子注入层(EIL)或电子传输层(ETL)(106)、和阴极(107),在该元件中,有机薄膜层为由空穴注入层(HIL)(103)、空穴传输层(HTL)(104)、发光层(105)、电子阻挡层(EBL)、电子注入层(EIL)或电子传输层(ETL)(106)构成的层叠结构,在形成这些有机薄膜层的层中,至少一层含有本发明的苝醌类有机化合物,由此,可以降低有机电子器件的驱动电压,还可以实现长寿命化。
另外相对于形成含有本发明的苝醌类有机化合物的有机薄膜层的层,该材料的含量优选为1-100摩尔%。
在本发明的有机电子器件中位于阳极(102)和发光层(105)之间的区域(空穴传输带区域)的层,具体而言是空穴注入层(HIL)(103)、或空穴传输层(HTL)(104),较好的有本发明的苝醌类有机化合物。另外,如本实施方式,在具有空穴注入层(103)和空穴传输层(104)二者的元件中,较好的空穴传输层(104)含有上述材料。
另外,将本发明的苝醌类有机化合物用于空穴传输区域的层中时,可以由本发明的化合物单独形成空穴注入层或空穴传输层,也可以与其他的材料混合使用。
按照本发明的发光器件,其发光波长在300到1200nm之间,较好的是在350到1000nm之间,更好的是在400到900nm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
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。
实施例1合成化合物DPA-1
化合物A2的合成:
将化合物A1(3.92g,10mmol),1mol/L NaOH溶液10ml和蒸馏水20ml在70度下搅拌30min,加入Br2 1.2ml继续70度下搅拌24h,然后减压下除去溶剂,用二氯甲烷为洗脱液使剩余物经过硅胶柱已得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物A2(4.85g,67%),MS:[M+H]+=564。
化合物A3的合成:
将叔丁醇钠(2.43g,25mmol)和丙二腈(1.32g,20mmol)在氮气,干燥四氢呋喃条件下,搅拌15min,在室温条件下加入A2(2.82g,5mmol),Pd(PPh3)4(3.4g,3mmol),碘化亚铜(3.9g,20mmol)之后60度条件下搅拌12小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到A3(1.65g,65%)MS:[M+H]+=509。
化合物DPA-1的合成:
使用冰醋酸将A3(5.09g,10mmol)溶解,之后冷却至0度,然后加入硝酸与氢溴酸的混合物,添加完成后室温搅拌,使用蒸馏水淬灭反应,固体析出之后继续搅拌,之后得到固体,DPA-1(3.57g,71%)MS:[M+H]+=505。
实施例2合成化合物DPA-2
化合物A4的合成:
将叔丁醇钠(2.43g,25mmol)和4-氰基-2,3,5,6-四氟苄腈(4.28g,20mmol)在氮气,干燥四氢呋喃条件下,搅拌15min,在室温条件下加入A2(2.82g,5mmol),Pd(PPh3)4(3.4g,3mmol),碘化亚铜(3.9g,20mmol)之后60度条件下搅拌12小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到A4(1.28g,47%)MS:[M+H]+=1101。
化合物DPA-2的合成:
使用冰醋酸将A4(11.00g,10mmol)溶解,之后冷却至0度,然后加入硝酸与氢溴酸的混合物,添加完成后室温搅拌,使用蒸馏水淬灭反应,固体析出之后继续搅拌,之后得到白色固体,DPA-2(3.27g,30%)MS:[M+H]+=1093。
实施例3合成化合物DPA-4
化合物A6的合成:
将叔丁醇钠(2.43g,25mmol)和六氟丙烷(3.04g,20mmol)在氮气,干燥四氢呋喃条件下,搅拌15min,在室温条件下加入A2(2.82g,5mmol),Pd(PPh3)4(3.4g,3mmol),碘化亚铜(3.9g,20mmol)之后60度条件下搅拌12小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到A6(1.71g,81%)MS:[M+H]+=849。
化合物DPA-4的合成:
使用冰醋酸将A6(8.49g,10mmol)溶解,之后冷却至0度,然后加入硝酸与氢溴酸的混合物,添加完成后室温搅拌,使用蒸馏水淬灭反应,固体析出之后继续搅拌,之后得到固体,DPA-4(4.45g,53%)MS:[M+H]+=841。
实施例4合成化合物DPA-8
化合物A12的合成:
将叔丁醇钠(2.43g,25mmol)和4-氰基-2,3,5,6-四氟苄腈(4.28g,20mmol)在氮气,干燥四氢呋喃条件下,搅拌15min,在室温条件下加入A9(3.06g,5mmol),Pd(PPh3)4(3.4g,3mmol),碘化亚铜(3.9g,20mmol)之后60度条件下搅拌12小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到A12(1.80g,69%)MS:[M+H]+=1149。
化合物DPA-8的合成:
使用冰醋酸将A11(11.48g,10mmol)溶解,之后冷却至0度,然后加入硝酸与氢溴酸的混合物,添加完成后室温搅拌,使用蒸馏水淬灭反应,固体析出之后继续搅拌,之后得到固体,DPA-8(6.16g,54%)MS:[M+H]+=1141。
实施例5合成化合物DPA-9
化合物A14的合成:
将化合物A13(4.51g,10mmol),1mol/LnaOH溶液10ml和蒸馏水20ml在70度下搅拌30min,加入Br2 1.2ml继续70度下搅拌24h,然后减压下除去溶剂,用二氯甲烷为洗脱液使剩余物经过硅胶柱已得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物A14(2.50g,40%),MS:[M+H]+=624。
化合物A15的合成:
将叔丁醇钠(2.43g,25mmol)和4-氰基-2,3,5,6-四氟苄腈(4.28g,20mmol)在氮气,干燥四氢呋喃条件下,搅拌15min,在室温条件下加入A14(3.12g,5mmol),Pd(PPh3)4(3.4g,3mmol),碘化亚铜(3.9g,20mmol)之后60度条件下搅拌12小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到A15(1.31g,45%)MS:[M+H]+=1161。
化合物DPA-9的合成:
使用冰醋酸将A15(11.60g,10mmol)溶解,之后冷却至0度,然后加入硝酸与氢溴酸的混合物,添加完成后室温搅拌,使用蒸馏水淬灭反应,固体析出之后继续搅拌,之后得到固体,DPA-9(7.08g,61%)MS:[M+H]+=1153。
实施例6合成化合物DPA-10
化合物A16的合成:
将叔丁醇钠(2.43g,25mmol)和丙二腈(1.32g,20mmol)在氮气,干燥四氢呋喃条件下,搅拌15min,在室温条件下加入A14(3.12g,5mmol),Pd(PPh3)4(3.4g,3mmol),碘化亚铜(3.9g,20mmol)之后60度条件下搅拌12小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到A16(0.76g,45%)MS:[M+H]+=569。
化合物DPA-10的合成:
使用冰醋酸将A16(5.68g,10mmol)溶解,之后冷却至0度,然后加入硝酸与氢溴酸的混合物,添加完成后室温搅拌,使用蒸馏水淬灭反应,固体析出之后继续搅拌,之后得到固体,DPA-10(1.06g,19%)MS:[M+H]+=561。
实施例7合成化合物DPA-11
化合物A18的合成:
将化合物A17(4.18g,10mmol),1mol/L NaOH溶液10ml和蒸馏水20ml在70度下搅拌30min,加入Br2 1.2ml继续70度下搅拌24h,然后减压下除去溶剂,用二氯甲烷为洗脱液使剩余物经过硅胶柱已得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物A18(4.48g,76%),MS:[M+H]+=590。
化合物A19的合成:
将叔丁醇钠(2.43g,25mmol)和4-氰基-2,3,5,6-四氟苄腈(4.28g,20mmol)在氮气,干燥四氢呋喃条件下,搅拌15min,在室温条件下加入A18(2.95g,5mmol),Pd(PPh3)4(3.4g,3mmol),碘化亚铜(3.9g,20mmol)之后60度条件下搅拌12小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到A19(1.88g,67%)MS:[M+H]+=1127。
化合物DPA-11的合成:
使用冰醋酸将A19(11.26g,10mmol)溶解,之后冷却至0度,然后加入硝酸与氢溴酸的混合物,添加完成后室温搅拌,使用蒸馏水淬灭反应,固体析出之后继续搅拌,之后得到固体,DPA-11(7.72g,65%)MS:[M+H]+=1119。
实施例8合成化合物DPA-13
化合物A22的合成:
将化合物A21(4.19g,10mmol),1mol/L NaOH溶液10ml和蒸馏水20ml在70度下搅拌30min,加入Br2 1.2ml继续70度下搅拌24h,然后减压下除去溶剂,用二氯甲烷为洗脱液使剩余物经过硅胶柱已得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物A22(4.46g,77%),MS:[M+H]+=592。
化合物A23的合成:
将叔丁醇钠(2.43g,25mmol)和4-氰基-2,3,5,6-四氟苄腈(4.28g,20mmol)在氮气,干燥四氢呋喃条件下,搅拌15min,在室温条件下加入A22(2.96g,5mmol),Pd(PPh3)4(3.4g,3mmol),碘化亚铜(3.9g,20mmol)之后60度条件下搅拌12小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到A23(1.86g,65%)MS:[M+H]+=1129。
化合物DPA-13的合成:
使用冰醋酸将A23(11.28g,10mmol)溶解,之后冷却至0度,然后加入硝酸与氢溴酸的混合物,添加完成后室温搅拌,使用蒸馏水淬灭反应,固体析出之后继续搅拌,之后得到固体,DPA-13(7.70g,64%)MS:[M+H]+=1121。
实施例9合成化合物DPA-15
化合物A26的合成:
将化合物A25(5.04g,10mmol),1mol/L NaOH溶液10ml和蒸馏水20ml在70度下搅拌30min,加入Br2 1.2ml继续70度下搅拌24h,然后减压下除去溶剂,用二氯甲烷为洗脱液使剩余物经过硅胶柱已得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物A26(3.92g,58%),MS:[M+H]+=676。
化合物A27的合成:
将叔丁醇钠(2.43g,25mmol)和4-氰基-2,3,5,6-四氟苄腈(4.28g,20mmol)在氮气,干燥四氢呋喃条件下,搅拌15min,在室温条件下加入A26(3.38g,5mmol),Pd(PPh3)4(3.4g,3mmol),碘化亚铜(3.9g,20mmol)之后60度条件下搅拌12小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到A23(1.18g,39%)MS:[M+H]+=1213。
化合物DPA-15的合成:
使用冰醋酸将A27(12.13g,10mmol)溶解,之后冷却至0度,然后加入硝酸与氢溴酸的混合物,添加完成后室温搅拌,使用蒸馏水淬灭反应,固体析出之后继续搅拌,之后得到固体,DPA-15(7.00g,58%)MS:[M+H]+=1205。
实施例10合成化合物DPA-17
化合物A29的合成:
将叔丁醇钠(2.43g,25mmol)和二氟甲烷(1.04g,20mmol)在氮气,干燥四氢呋喃条件下,搅拌15min,在室温条件下加入A22(2.96g,5mmol),Pd(PPh3)4(3.4g,3mmol),碘化亚铜(3.9g,20mmol)之后60度条件下搅拌12小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到A29(1.13g,94%)MS:[M+H]+=481。
化合物DPA-17的合成:
使用冰醋酸将A29(4.80g,10mmol)溶解,之后冷却至0度,然后加入硝酸与氢溴酸的混合物,添加完成后室温搅拌,使用蒸馏水淬灭反应,固体析出之后继续搅拌,之后得到固体,DPA-17(4.02,85%)MS:[M+H]+=473。
实施例11合成化合物DPA-19
化合物A32的合成:
将化合物A31(4.51g,10mmol),1mol/L NaOH溶液10ml和蒸馏水20ml在70度下搅拌30min,加入Br2 1.2ml继续70度下搅拌24h,然后减压下除去溶剂,用二氯甲烷为洗脱液使剩余物经过硅胶柱已得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物A18(4.48g,87%),MS:[M+H]+=624。
化合物A33的合成:
将叔丁醇钠(2.43g,25mmol)和4-氰基-2,3,5,6-四氟苄腈(4.28g,20mmol)在氮气,干燥四氢呋喃条件下,搅拌15min,在室温条件下加入A32(3.12g,5mmol),Pd(PPh3)4(3.4g,3mmol),碘化亚铜(3.9g,20mmol)之后60度条件下搅拌12小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到A33(1.01g,35%)MS:[M+H]+=1161。
化合物DPA-19的合成:
使用冰醋酸将A19(11.60g,10mmol)溶解,之后冷却至0度,然后加入硝酸与氢溴酸的混合物,添加完成后室温搅拌,使用蒸馏水淬灭反应,固体析出之后继续搅拌,之后得到固体,DPA-19(8.64g,75%)MS:[M+H]+=1153。
实施例12合成化合物DPA-36
化合物A35的合成:
将化合物A34(4.44g,10mmol),1mol/L NaOH溶液10ml和蒸馏水20ml在70度下搅拌30min,加入Br2 1.2ml继续70度下搅拌24h,然后减压下除去溶剂,用二氯甲烷为洗脱液使剩余物经过硅胶柱已得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物A35(3.26g,53%),MS:[M+H]+=616。
化合物DPA-36的合成:
将叔丁醇钠(2.43g,25mmol)和A36(1.66g,20mmol)在氮气,干燥四氢呋喃条件下,搅拌15min,在室温条件下加入A35(3.08g,5mmol),Pd(PPh3)4(3.4g,3mmol),碘化亚铜(3.9g,20mmol)之后60度条件下搅拌12小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到粗产物,使用冰醋酸将粗产品溶解,之后冷却至0度,然后加入硝酸与氢溴酸的混合物,添加完成后室温搅拌,使用蒸馏水淬灭反应,固体析出之后继续搅拌,之后得到固体,DPA-36(2.26g,36%)MS:[M+H]+=628。
实施例13合成化合物DPA-41
化合物A38的合成:
将化合物A37(5.44g,10mmol),1mol/L NaOH溶液10ml和蒸馏水20ml在70度下搅拌30min,加入Br2 1.2ml继续70度下搅拌24h,然后减压下除去溶剂,用二氯甲烷为洗脱液使剩余物经过硅胶柱已得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物A38(4.77g,67%),MS:[M+H]+=712。
化合物DPA-41的合成:
将叔丁醇钠(2.43g,25mmol)和A39(1.51g,20mmol)在氮气,干燥四氢呋喃条件下,搅拌15min,在室温条件下加入A38(3.56g,5mmol),Pd(PPh3)4(3.4g,3mmol),碘化亚铜(3.9g,20mmol)之后60度条件下搅拌12小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到粗产物,使用冰醋酸将粗产品溶解,之后冷却至0度,然后加入硝酸与氢溴酸的混合物,添加完成后室温搅拌,使用蒸馏水淬灭反应,固体析出之后继续搅拌,之后得到固体,DPA-41(3.09g,45%)MS:[M+H]+=687。
实施例14合成化合物DPA-128
化合物A41的合成:
将化合物A40(4.51g,10mmol),1mol/L NaOH溶液10ml和蒸馏水20ml在70度下搅拌30min,加入Br2 1.2ml继续70度下搅拌24h,然后减压下除去溶剂,用二氯甲烷为洗脱液使剩余物经过硅胶柱已得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物A41(4.04g,65%),MS:[M+H]+=623。
化合物DPA-128的合成:
将叔丁醇钠(2.43g,25mmol)和五氟苯胺(3.66g,20mmol)在氮气,干燥四氢呋喃条件下,搅拌15min,在室温条件下加入A41(3.13g,5mmol),Pd(PPh3)4(3.4g,3mmol),碘化亚铜(3.9g,20mmol)之后60度条件下搅拌12小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到粗产物,使用冰醋酸将粗产品溶解,之后冷却至0度,然后加入硝酸与氢溴酸的混合物,添加完成后室温搅拌,使用蒸馏水淬灭反应,固体析出之后继续搅拌,之后得到固体,DPA-128(5.05g,49%)MS:[M+H]+=1031。
实施例15合成化合物DPA-141
化合物A43的合成:
将化合物A42(3.96g,10mmol),1mol/L NaOH溶液10ml和蒸馏水20ml在70度下搅拌30min,加入Br2 1.2ml继续70度下搅拌24h,然后减压下除去溶剂,用二氯甲烷为洗脱液使剩余物经过硅胶柱已得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物A43(1.64g,29%),MS:[M+H]+=568。
化合物DPA-141的合成:
将叔丁醇钠(2.43g,25mmol)、A44(1.16g,5mmol)、A45(0.21g,5mmol)和丙二腈(0.66g,10mmol)在氮气,干燥四氢呋喃条件下,搅拌15min,在室温条件下加入A43(2.84g,5mmol),Pd(PPh3)4(3.4g,3mmol),碘化亚铜(3.9g,20mmol)之后60度条件下搅拌12小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到粗产物,使用冰醋酸将粗产品溶解,之后冷却至0度,然后加入硝酸与氢溴酸的混合物,添加完成后室温搅拌,使用蒸馏水淬灭反应,固体析出之后继续搅拌,之后得到固体,DPA-141(4.62g,73%)MS:[M+H]+=633。
实施例16合成化合物DPA-225
化合物A47的合成:
将化合物A46(4.96g,10mmol),1mol/LNaOH溶液10ml和蒸馏水20ml在70度下搅拌30min,加入Br2 1.2ml继续70度下搅拌24h,然后减压下除去溶剂,用二氯甲烷为洗脱液使剩余物经过硅胶柱已得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物A47(3.84g,59%),MS:[M+H]+=651。
化合物DPA-225的合成:
将叔丁醇钠(2.43g,25mmol)和丙二腈(1.32g,20mmol)在氮气,干燥四氢呋喃条件下,搅拌15min,在室温条件下加入A47(3.26g,5mmol),Pd(PPh3)4(3.4g,3mmol),碘化亚铜(3.9g,20mmol)之后60度条件下搅拌12小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到粗产物,使用冰醋酸将粗产品溶解,之后冷却至0度,然后加入硝酸与氢溴酸的混合物,添加完成后室温搅拌,使用蒸馏水淬灭反应,固体析出之后继续搅拌,之后得到固体,DPA-225(5.03g,81%)MS:[M+H]+=621。
实施例17合成化合物DPA-231
化合物A49的合成:
将化合物A48(3.52g,10mmol),1mol/LNaOH溶液10ml和蒸馏水20ml在70度下搅拌30min,加入Br2 1.2ml继续70度下搅拌24h,然后减压下除去溶剂,用二氯甲烷为洗脱液使剩余物经过硅胶柱已得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物A49(4.46g,88%),MS:[M+H]+=507。
化合物DPA-231的合成:
将叔丁醇钠(2.43g,25mmol)和丙二腈(1.00g,15mmol)在氮气,干燥四氢呋喃条件下,搅拌15min,在室温条件下加入A49(2.54g,5mmol),Pd(PPh3)4(3.4g,3mmol),碘化亚铜(3.9g,20mmol)之后60度条件下搅拌12小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到粗产物,使用冰醋酸将粗产品溶解,之后冷却至0度,然后加入硝酸与氢溴酸的混合物,添加完成后室温搅拌,使用蒸馏水淬灭反应,固体析出之后继续搅拌,之后得到固体,DPA-231(3.45g,75%)MS:[M+H]+=461。
OLED器件的制备与表征
OLED器件各层所使用的材料:
有机化合物材料的能级可通过量子计算得到,比如利用TD-DFT(含时密度泛函理论)通过Gaussian09W(Gaussian Inc.),具体的模拟方法可参见WO2011141110。首先用半经验方法“Ground State/Semi-empirical/Default Spin/AM1”(Charge 0/Spin Singlet)来优化分子几何结构,然后有机分子的能量结构由TD-DFT(含时密度泛函理论)方法算得“TD-SCF/DFT/Default Spin/B3PW91”与基组“6-31G(d)”(Charge 0/Spin Singlet)。HOMO和LUMO能级按照下面的校准公式计算,S1,T1和谐振因子f(S1)直接使用。
HOMO(eV)=((HOMO(G)×27.212)-0.9899)/1.1206
LUMO(eV)=((LUMO(G)×27.212)-2.0041)/1.385
其中HOMO,LUMO,T1和S1是Gaussian 09W的直接计算结果,单位为Hartree。结果如下表1所示:
表1
器件结构为:ITO/HIL(10nm)/HT-1(120nm)/HT-2(10nm)/BH:BD(25nm)/ET:Liq(30nm)/Liq(1nm)/Al(100nm),具体制备步骤如下:
a、导电玻璃基片的清洗:首次使用时,可用多种溶剂进行清洗,例如氯仿、酮、异丙醇进行清洗,然后进行紫外臭氧等离子处理;
b、HIL(10nm),HT-1(120nm),HT-2(10nm),EML(20nm),ETL(30nm):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,HT-1和DPA-1以98:2的比例共蒸镀形成10nm的注入层(HIL),之后依次蒸镀得到120nm的HT-1以及10nm的HT-2层。随后BH和BD以97:3的比例共蒸镀形成25nm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。
所有器件除HI采用不同的化合物作为掺杂剂,其他实施方案均相同。各OLED器件的电流电压(J-V)特性通过表征设备来表征,同时记录重要的参数如效率,寿命及外部量子效率。见表2。经检测,采用化合物DPA-1~化合物DPA-231作为HTL层的掺杂剂,所得到器件的效率和寿命相比F4TCNQ都有提高。
表2
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本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 (4)
2.一种混合物,其特征在于,包含有至少一种权利要求1所述的苝醌类有机化合物,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,主体材料或有机染料。
3.一种组合物,其特征在于,所述组合物包含权利要求1所述的苝醌类有机化合物,及至少有机溶剂。
4.一种有机电子器件,其特征在于,所述有机电子器件包含权利要求1所述的苝醌类有机化合物,或权利要求2所述的混合物。
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