CN102892860A - 四配位金络合物的合成及其在光发射设备中的应用 - Google Patents
四配位金络合物的合成及其在光发射设备中的应用 Download PDFInfo
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- CN102892860A CN102892860A CN2011800243489A CN201180024348A CN102892860A CN 102892860 A CN102892860 A CN 102892860A CN 2011800243489 A CN2011800243489 A CN 2011800243489A CN 201180024348 A CN201180024348 A CN 201180024348A CN 102892860 A CN102892860 A CN 102892860A
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Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/12—Gold compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
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Abstract
公开了表现出光吸收和光发射性质的金络合物,以及制备和使用所述金络合物的方法。
Description
发明背景
技术领域
本公开涉及能够吸收和/或发射光并且因此在设备中用作放射性或吸收材料的金络合物。
技术背景
能够吸收和/或发射光的化合物非常适合用于许多光学和电光设备中,包括光吸收设备(例如太阳能和光敏设备)、光发射设备(例如有机光发射二极管(OLED))或能够吸收和发射光的设备。许多研究已经致力于发现并优化用于光学和电光设备中的有机和有机金属材料。通常,该领域中的研究旨在实现许多目标,包括提高吸收和发射效率,以及提高加工能力等。
尽管在致力于光学和电光材料的研究中有重大进展,但是包括有机或有机金属材料的许多当前设备尚待优化。当前用于光学和电光设备中的许多材料有很多缺点,包括加工能力差、发射或吸收无效和稳定性不够理想等。因此,需要在光学和电光设备中表现出改进性能的新材料。本发明满足了这种需要和其它需要。
发明概述
本发明涉及显示出光吸收和光发射的金络合物,制备此类化合物的方法及其应用,包括包含所述化合物的光学设备。
在一个实施方案中,所述化合物由下式表示:
其中(R1)2和(R2)2中的每个R1和R2独立地表示氢、经任选取代的C1-C4烷基、卤素、羟基、氨基、硝基或硫醇基;
Y1a表示O、S、NR4a,其中R4a表示经任选取代的C1-C4烷基;Si(R4b)2,其中(R4b)2中的每个R4b独立地表示经任选取代的C1-C4烷基;或C(R4c)2,其中(R4c)2中的每个R4c表示氢或经任选取代的C1-C4烷基;
n为整数0或1;
Y1b,存在时,表示O、S、NR5a,其中R5a表示经任选取代的C1-C4烷基;Si(R5b)2,其中(R5b)2中的每个R5b独立地表示经任选取代的C1-C4烷基;或C(R5c)2,其中(R5c)2中的每个R5c表示氢或经任选取代的C1-C4烷基;
Y2a、Y2b、Y2c和Y2d各自独立地表示N、NR6a或CR6b,其中R6a和R6b各自独立地表示氢、经任选取代的C1-C4烷基、卤素、羟基、氨基、硝基或硫醇基;
Y3a、Y3b、Y3c、Y3d、Y3e、Y4a、Y4b、Y4c和Y4d各自独立地表示N、O、S、NR6a、CR6b,其中R6a和R6b各自独立地表示氢或经任选取代的C1-C4烷基;或Z(R6c)2,其中Z为C或Si,并且其中(R6c)2中的每个R6c独立地表示氢或经任选取代的C1-C4烷基;
其中m为整数1或2;
条件是如果m为1,Y2a和Y2d各自为CH并且Y2b或Y2c为N,则Y4a、Y4b、Y3a或Y3d中的至少一个不为N;并且
条件是如果n为0,m为2,Y2a和Y2d各自为CH并且Y2b或Y2c为N,则Y3b或Y3c中的至少一个不为N。
还公开了光学设备,例如包含作为功能材料的本发明的一种或多种化合物的有机光发射设备、光伏设备(例如,太阳能电池)和发光显示设备,例如光发射体或吸收体,或二者。
附图简述
并入并构成本说明书的一部分的附图说明了几个方面并连同描述一起用于解释本发明的原理。
图1为示例性有机光发射二极管(OLED)的横截面图。
图2说明了:(A)示例性四配位金络合物2-(3-(吡啶-2-基)苯氧基)-6-(吡啶-2-基氧基)苯基]Au(III)Cl,及(B)其在未处理(未脱气)的二氯甲烷(DCM)和脱气(起泡)DCM中的室温发射光谱。
图3为由特定实施方案,在77K下于2-甲基四氢呋喃中获得的2-(3-(吡啶-2-基)苯氧基)-6-(吡啶-2-基氧基)苯基]Au(III)Cl产生的光致发光光谱。
图4为由特定实施方案,在77K下于2-甲基四氢呋喃中获得并且在室温下于二氯甲烷中脱气的[2-(3-(6-(3-甲基-1H-吡唑-5-基)吡啶-2-基氧基)苯氧基)吡啶]Au(III)Cl产生的光致发光光谱。
本发明另外的方面将部分在以下描述中列出,并且部分将从描述中显而易见,或可通过本发明的实践学到。凭借所附权利要求中特别指出的元素和组合将实现并获得本发明的优点。应理解,前述一般描述和以下详细描述均仅为示例性和说明性,如所声明的,并不限制本发明。
发明详述
参考本发明的以下详细描述和其中包括的实施例可更容易地理解本发明。
在公开和描述现存化合物、设备和/或方法之前,应理解除非另有说明它们不限于特定合成方法,或除非另有说明不限于特殊试剂,当然,同样可变化。还应理解,本文所用术语仅仅是为了描述特殊方面的目的并不旨在限制。虽然在本发明的实践或试验中可使用与本文所述方法和材料相似或等效的任何方法和材料,但是现在描述示例性方法和材料。
如说明书和所附权利要求中所使用,除非上下文另外明确指出,单数形式“一个”、“一种”和“所述”包括复数指示物。因此,例如,提到“一种组分”包括两种或更多种组分的混合物。
本文可将范围表示为从“约”一个特殊值,和/或至“约”另一个特殊值。在表示此类范围时,另一方面包括从一个特殊值和/或至其它特殊值。类似地,通过使用先行词“约”将值表示为近似值时,应理解特殊值形成了另一方面。应进一步理解,每个范围的端点,与其它端点有关和独立于其它端点,均很重要。还应理解,本文公开了许多值,并且除值本身以外,本文还将每个值公开为“约”该特殊值。例如,如果公开值“10”,则还公开了“约10”。还应理解,还公开了两个特殊单位之间的每个单位。例如,如果公开了10和15,则还公开了11、12、13和14。
如本文所使用,术语“任选”或“任选地”指随后描述的事件或情况可以发生或可以不发生,并且描述包括所述事件或情况发生的实例和不发生的实例。
如本文所使用的术语“烷基”为1-24个碳原子的支链或直链饱和烃基,例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、仲戊基、新戊基、己基、庚基、辛基、壬基、癸基、十二烷基、十四烷基、十六烷基、二十烷基、二十四烷基等。烷基可为环状或非环状。烷基可为支链或直链。烷基也可经取代或未经取代。例如,烷基可经一个或多个基团取代,包括但不限于如本文所述的经任选取代的烷基、环烷基、烷氧基、氨基、醚、卤化物、羟基、硝基、甲硅烷基、硫代-氧代或硫醇基。“低级烷基”为含有1-6个(例如,1-4个)碳原子的烷基。
如本文所使用的术语“胺”或“氨基”用式NA1A2A3表示,其中A1、A2和A3可独立地为如本文所述的氢或经任选取代的烷基、环烷基、烯基、环烯基、炔基、环炔基、芳基或杂芳基。
如本文所使用的术语“卤化物”指卤素氟、氯、溴和碘。
如本文所使用的术语“羟基”用式-OH表示。
如本文所使用的术语“硝基”用式-NO2表示。
如本文所使用的术语“腈”用式-CN表示。
如本文所使用的术语“硫醇基”用式-SH表示。
公开了用于制备本发明的组合物的组分以及在本文公开的方法中使用的组合物本身。本文公开了这些和其它材料,并且应理解,当公开这些材料的组合、亚类、相互作用、群等时,虽然可以不明确公开这些化合物的每个不同的单独和集体组合及排列的特定参考,但是本文特别包括并描述了每一个。例如,如果公开并讨论了特殊化合物并且讨论了可对包括所述化合物在内的许多分子进行的许多修饰,除非特别指出相反,则特别包括所述化合物的每一种组合及排列和可能的修饰。因此,如果公开了一类分子A、B和C以及一类分子D、E和F并且公开了组合分子A-D的实例,则即使未单独列举每一个分子,但是每一个均是单独和集体包括的有意义组合,考虑公开A-E、A-F、B-D、B-E、B-F、C-D、C-E和C-F。同样,还公开了这些分子的任何亚类或组合。因此,例如,将考虑公开A-E、B-F和C-E的子群。这种概念适用于本申请的所有方面,包括但不限于制备和使用本发明组合物的方法的步骤。因此,如果有多种可进行的附加步骤,应理解可用本发明方法的任何特定实施方案或实施方案的组合进行这些附加步骤的每一步。
在整篇说明书中,应理解,其中利用字母和/或符号表示原子或官能团,并且其中存在相同字母和/或符号的多个实例,每个单独实例可表示与使用相同字母和/或符号的任何其它实例相同或不同的种类(例如,原子和/或官能团)。类似地,将金属描绘成化学结构的一部分时,标记可指单个金属原子和/或多个原子。一方面,金属的标记指单个金属原子。另一方面,金属的标记指多个金属原子。
一方面,本申请公开了磷光性多齿配位基(例如,三齿配位基和/或四齿配位基)金(III)络合物。另一方面,例如可通过修饰配体结构将此发明络合物的发射(例如)从紫外线调整到近红外。另一方面,本发明金络合物可具有比传统发射络合物更高的稳定性和效率。又一方面,本发明金络合物可用作发光标记(例如,在生物应用中)、抗癌剂、光伏吸收体、发射体(在有机光发射二极管(OLED)中)或其组合。
一方面,本公开的发明性金络合物用下式表示:
其中Ar1、Ar2、Ar3和Ar4,如果存在,表示芳族基,每个E表示任选的连接基团,例如,碳或氧,并且R表示辅助配体。
在各个方面,辅助配体可包含以下的一种或多种:
其中辅助配体的R1-R10各自独立地表示氢原子、烷基、卤代烷基、芳烷基、烯基、炔基、芳基、氨基、单或二烷基氨基、单或二芳基氨基、烷氧基、芳氧基、杂芳氧基、烷氧基羰基、酰氧基、酰氨基、烷氧基羰基氨基、芳氧基羰基氨基、磺酰氨基、氨磺酰基、氨甲酰基、烷硫基、亚磺酰基、脲基、磷酰胺基、羟基、巯基、卤原子、氰基、磺基、羧基、硝基、肼基、经取代的甲硅烷基或可聚合基团;进一步地,其中存在多个R,R的数量应从0至约4,并且每个R可与任何其它R相同或不同。一方面,辅助配体可包含氢原子。另一方面,辅助配体可包含烷基。另一方面,辅助配体可包含卤代烷基。另一方面,辅助配体可包含芳烷基。另一方面,辅助配体可包含烯基。另一方面,辅助配体可包含炔基。另一方面,辅助配体可包含芳基。另一方面,辅助配体可包含氨基。另一方面,辅助配体可包含烷氧基、芳氧基、杂芳氧基、烷氧基羰基、酰氧基或其组合。在其它方面,辅助配体可包含酰氨基、烷氧基羰基氨基、芳氧基羰基氨基、磺酰基氨基、氨磺酰基、氨甲酰基、烷硫基、亚磺酰基、脲基、磷酰胺基、羟基、巯基、卤原子、氰基、磺基、羧基、硝基、肼基、经取代的甲硅烷基、可聚合基团或其组合。
在更多其它方面,辅助配体可包含与本文特别列举的一个或多个基团差异,并且本发明并非旨在限于任何特殊辅助配体。
在各个方面,可按配体类别分组并说明本发明组合物的特定非限制性实例。一方面,本发明组合物可用通式表示:
其中Au表示金,N表示氮取代的芳族基,每个E表示任选连接原子,例如,碳或氧,X表示卤素或其它带负电的基团,并且每个C表示芳族基。这类配体中本发明组合物的特定实例可包括:
或其组合。
一方面,本发明组合物可用通式表示:
其中Au表示金,每个E表示任选连接原子,例如,碳或氧,R表示辅助配体,并且每个C表示芳族基。这类配体中本发明组合物的特定实例可包括:
或其组合。
一方面,本发明组合物可用通式表示:
其中Au表示金,N表示氮取代的芳族基,每个E表示任选的连接原子,例如,碳或氧,R表示辅助配体,并且每个C表示芳族基。这类配体中本发明组合物的特定实例可包括:
一方面,本发明组合物可用通式表示:
其中Au表示金,每个N表示氮取代的芳族基,每个E表示任选的连接原子,例如,碳或氧,R表示辅助配体,并且C表示芳族基。这类配体中本发明组合物的特定实例可包括:
一方面,本发明组合物可用通式表示:
其中Au表示金,N表示氮取代的芳族基,每个E表示任选的连接原子,例如,碳或氧,并且每个C表示芳族基。这类配体中本发明组合物的特定实例可包括:
一方面,本发明组合物可用通式表示:
其中Au表示金,N表示氮取代的芳族基,每个E表示任选的连接原子,例如,碳或氧,并且每个C表示芳族基。这类配体中本发明组合物的特定实例可包括:
一方面,本发明组合物可用通式表示:
其中Au表示金,每个E表示任选的连接原子,例如,碳或氧,并且每个C表示芳族基。这类配体中本发明组合物的特定实例可包括:
一方面,本发明组合物可用通式表示:
其中Au表示金,每个N表示氮取代的芳族基,每个E表示任选的连接原子,例如,碳或氧,并且每个C表示芳族基。这类配体中本发明组合物的特定实例可包括:
另一方面,本发明组合物可用通式表示:
其中(R1)2和(R2)2中的每个R1和R2独立地表示氢、经任选取代的C1-C4烷基、卤素、羟基、氨基、硝基或硫醇基;R3表示甲基、乙基、丙基或丁基;Y1a表示O、S、NR4a,其中R4a表示经任选取代的C1-C4烷基;Si(R4b)2,其中(R4b)2中的每个R4b独立地表示经任选取代的C1-C4烷基;或C(R4c)2,其中(R4c)2中的每个R4c表示氢或经任选取代的C1-C4烷基;n为整数0或1;Y1b,存在时,表示O、S、NR5a,其中R5a表示经任选取代的C1-C4烷基;Si(R5b)2,其中(R5b)2中的每个R5b独立地表示经任选取代的C1-C4烷基;或C(R5c)2,其中(R5c)2中的每个R5c表示氢或经任选取代的C1-C4烷基;Y2a、Y2b、Y2c和Y2d各自独立地表示N、NR6a或CR6b,其中R6a和R6b各自独立地表示氢、经任选取代的C1-C4烷基、卤素、羟基、氨基、硝基或硫醇基;Y3a、Y3b、Y3c、Y3d、Y3e、Y4a、Y4b、Y4c和Y4d各自独立地表示N、O、S、NR6a、CR6b,其中R6a和R6b各自独立地表示氢或经任选取代的C1-C4烷基;或Z(R6c)2,其中Z为C或Si,并且其中(R6c)2中的每个R6c独立地表示氢或经任选取代的C1-C4烷基;m为整数1或2;其中开口虚线圆指与之缔合的环部分或完全不饱和。
在上式的一个实施方案中,如果m为1,Y2a或Y2d为CH并且Y2c为N,则Y4a、Y4b、Y3a或Y3d中的至少一个不为N。例如,根据该实施方案,下列化合物不包括在上式中:
正如在上述实例中可见,m为1,Y2a和Y2d各自为CH并且Y2c为N。然而,Y4a、Y4b、Y3a或Y3d各自为N。由此得出结论,根据该实施方案,前述实例不包括在上述通式中。在该实施方案的实践中,相似分析可用于确定一种化合物是否包括在上述通式中。
在上述通式的另一实施方案中,如果n为0,m为2,Y2a和Y2d各自为CH,并且Y2b或Y2c为N,则Y3b或Y3c中的至少一个不为N。例如,根据该实施方案,下列化合物不包括在上式中:
正如在上述实例中可见,n为0,m为2,Y2a和Y2d各自为CH,并且Y2b为N。然而,Y3b和Y3c各自为N。由此得出结论,根据该实施方案,前述实例不包括在上述通式中。再次,在该实施方案的实践中,相似分析可用于确定一种化合物是否包括在上述通式中。
在上述通式的一个实施方案中,化合物由下式表示:
该式中特定实施方案的非限制性实例包括:
在上述通式的另一实施方案中,化合物由下式表示:
该式中特定实施方案的非限制性实例包括:
在上述通式的另一实施方案中,化合物由下式表示:
该式中特定实施方案的非限制性实例包括:
在上述通式的另一实施方案中,化合物由下式表示:
该式中特定实施方案的非限制性实例包括:
在上述通式的另一实施方案中,化合物由下式表示:
该式中特定实施方案的非限制性实例包括:
在上述通式的另一实施方案中,化合物由下式表示:
这些式中特定实施方案的非限制性实例包括:
在其它方面,可将通式的任何一个或多个和/或本文所述特定实例排除在本发明之外。例如,一方面,式
不包括在本发明内。
可使用多种方法制备本发明的化合物。在一个实施方案中,其中Y1a为O,可根据方案1提供化合物。
方案1
关于方案1,例如可通过使用催化量的偶联剂,例如CuI,使醇(尤其是苯酚)与卤代苯基偶联,完成步骤“a”。上述方案1中的变量“X”表示卤素(即,Cl、F、I、Br),并且当连同方案1使用时优选为I。
一方面,可单独使用多种方法制备络合金属的配体的每个侧面,所述方法通常取决于Y3a为N还是C。关于以下方案2,当Y4a为N时,可根据方案2(A)提供前体,其中卤代苯基化合物与吡唑、咪唑、1H-1,2,3-三唑、1H-四唑或2H-五唑反应。卤代苯基化合物可包含任何卤素(X),包括Cl、Br、F或I,但是优选为在偶联反应中通常更具活性的I。可使用金属或有机金属偶联剂,例如Cu2O,偶联卤代苯基化合物和相应吡唑、咪唑、1H-1,2,3-三唑、1H-四唑或2H-五唑。此类偶联反应期间,可有利于包括小摩尔比,例如约20mol%的除酸剂,例如顺-2-吡啶乙醛肟。
可选地,当Y4a为C时,可使用不同方法提供前体。关于以下方案2(B),使如以上讨论的卤代苯基与四唑、1,2,3-三唑、吡唑或吡咯反应以实现碳-碳键偶联,与方案2(A)所示碳-氮键偶联相反。也可使用小摩尔比的有机金属催化剂,例如Pd(II)催化剂(例如,Pd(OAc)2)实现碳-碳键偶联,所述有机金属催化剂通常与过量的盐混合物一起使用,例如KI和CuI。如本领域技术人员所了解,当采用方案2中所示每种偶联反应时,一方面,可有利于在干燥环境,例如在氩气下,或甚至在干燥箱中进行反应,以避免潮湿或掺杂氧。
方案2
一方面,本发明的化合物可用于多种光学应用中。作为发光材料时,该化合物可用于有机光发射二极管(OLED)、发光设备和显示器和/或其它光发射设备中。关于图3,例如,特定实施方案2-(3-(吡啶-2-基)苯氧基)-6-(吡啶-2-基氧基)苯基]Au(III)Cl显示出一系列波长的光致发光(吸收光之后发射光),从光谱的蓝光至红光部分。
另一方面,可通过改变金属中心周围配体的结构调整化合物的发射(和吸收)性质。例如,一方面,具有有吸电子取代基的配体的化合物可表现出与具有有供电子取代基的配体的化合物不同的光学性质,包括发射和吸收。通常,化学结构变化影响化合物的电子结构,从而影响化合物的吸收和发射性质。因此,在各个方面,可定制或调整本发明的化合物以适于需要特殊发射或吸收特征的特定应用。
在一个实施方案中,化合物可用于OLED中。图1示出了OLED100的横截面视图,所述OLED包括具有阳极104的衬底102(通常为透明材料,例如铟锡氧化物)、空穴传输材料层(HTL)106、光处理材料层108(例如放射性材料(EML),包括发射体和主体)、电子传输材料层(ETL)110和金属阴极层112。
在此类实施方案中,光处理材料层108可包含本发明的一种或多种化合物,任选和主体材料一起。主体材料,如果存在,可为本领域中已知的任何适合主体材料。由光处理材料108的发射能量(光能隙)确定OLED的发光颜色,如以上所讨论,可通过调整发射化合物和/或主体材料的电子结构调整发射能量。HTL层106中的空穴传输材料和/或ETL层110中的电子传输材料可包含本领域中已知的任何适合的空穴传输材料。其选择完全在本领域技术人员的范围之内。
显而易见的是,本发明的化合物可显示出磷光。磷光OLED(即,具有磷光发射体的OLED)通常具有比其它OLED(例如,荧光OLED)更高的设备效率。Baldo等的WO2000/070655中更详细地描述了基于电致磷光发射体的光发射设备,其通过这样参考对OLED,尤其是特殊磷光OLED的教导并入本文。
实施例
提出以下实施例以便为本领域的普通技术人员提供如何制备并评估本文要求保护的化合物、组合物、物品、设备和/或方法的完整公开和描述,旨在仅为本发明的实例并非旨在限制发明人当作其发明的范围。虽然已经努力确保关于数字(例如,量、温度等)的精确性,但是应将一些误差和偏差计算在内。除非另外指出,份为重量份,温度按℃计或为环境温度,并且压力为或接近大气压。
实施例1.特定实施方案[2-(3-(吡啶-2-基)苯氧基)-6-(吡啶-2-基氧基)苯基]Au(III)Cl的制备
3-(吡啶-2-基氧基)苯酚的合成:
在氮气下,将磁性搅拌棒、间苯二酚(110mmol)、2-溴吡啶(100mmol)、1-甲基咪唑(5mmol)和碳酸钾(200mmol)装入压力容器。添加吡啶(80mL)并且用氮气起泡20min,之后添加碘化亚铜(I)(10mmol)并再起泡10min。密封容器并搅拌加热至140℃。2天后,使溶液冷却。过滤掉固体并且用甲苯和甲醇的50∶50混合物冲洗。通过旋转蒸发减少滤液并且添加150ml含有10mL冰醋酸的水并剧烈振荡。将水轻轻倒出并添加50mL的DCM,形成乳白色沉淀,乳白色沉淀可通过真空过滤收集沉淀并用乙醚干燥,产生纯产物3-(吡啶-2-基氧基)苯酚,产率为55%。1H NMR(CDCl3):5.98(s,1H),6.59(s,1H),6.62-6.69(m,2H),6.94(d,1H),f7.02(dd,1H),7.23(vt,1H),7.70(dd,1H),8.23(b,1H)
2-(3-(3-溴苯氧基)苯氧基)吡啶的合成:
在氮气下,将磁性搅拌棒、3-(吡啶-2-基氧基)苯酚(50mmol)、2,6-二溴吡啶(50mmol)、1-甲基咪唑(25mmol)和碳酸钾(100mmol)装入压力容器。添加甲苯(80mL)并且用氮气起泡20min,之后添加碘化亚铜(I)(5mmol)并再使溶液起泡10min。密封容器并搅拌加热至140℃。2天后,使溶液冷却并过滤掉固体,并且用二氯甲烷冲洗固体。将滤液加入装有DCM和水的分液漏斗中。用75mL DCM洗涤水相3次,并且用纯净水洗涤结合有机层一次。收集有机层,用硫酸镁干燥,过滤,并通过旋转蒸发减少滤液。通过在二氧化硅上使用DCM进行柱色谱法纯化所生成的油,产生纯产物2-(3-(3-溴苯氧基)苯氧基)吡啶,产率为60%。1H NMR(CDCl3):6.80-6.85(m,2H),6.91(s,1H),6.94(s,1H),6.97-7.03(m,2H),7.19(vt,1H),7.21-7.24(m,2H),7.36(vt,1H),7.70(dd,1H),8.21(dd,1H)。
2-(3-(3-(吡啶-2-基)苯氧基)苯氧基)吡啶的合成:
在氮气下,将磁性搅拌棒、2-(3-(3-溴苯氧基)苯氧基)(10mmol)和2-(三丙基甲锡烷基)吡啶(10mmol)装入烤箱干燥的三颈烧瓶中。添加干燥甲苯(100mL)并用氮气起泡20min,之后添加四(三苯基膦)钯(0)(5mmol),再起泡10min,并使其回流2天。冷却后,过滤烧瓶的内含物,通过旋转蒸发减少液体,并且通过在二氧化硅上使用DCM进行柱色谱法纯化所生成的油,以产生纯产物2-(3-(3-(吡啶-2-基)苯氧基)苯氧基)吡啶,产率为65%。1H NMR(CDCl3):6.84(vt,1H),6.85-6.89(m,2H),6.91(d,1H),6.98(dd,1H),7.11(dd,1H),7.24(dd,1H),7.34(vt,1H),7.44(vt,1H),7.66-7.78(m,5H),8.19(dd,1H),8.67(dd,1H)。
[2-(3-(吡啶-2-基)苯氧基)-6-(吡啶-2-基氧基)苯基]Au(III)Cl的合成:
使2-(3-(3-(吡啶-2-基)苯氧基)苯氧基)吡啶(1mmol)、KAuCl4(1mmol)和醋酸(10mL)的混合物回流3天。使混合物冷却至室温。过滤掉所生成的白色络合物并用H2O、MeOH和Et2O洗涤,在真空下干燥成[2-(3-(吡啶-2-基)苯氧基)-6-(吡啶-2-基氧基)苯基]Au(III)Cl。
Claims (8)
1.一种化合物,所述化合物由下式表示:
其中(R1)2和(R2)2中的每个R1和R2独立地表示氢、经任选取代的C1-C4烷基、卤素、羟基、氨基、硝基或硫醇基;
R3表示甲基、乙基、丙基或丁基;
Y1a表示O、S、NR4a,其中R4a表示经任选取代的C1-C4烷基;Si(R4b)2,其中(R4b)2中的每个R4b独立地表示经任选取代的C1-C4烷基;或C(R4c)2,其中(R4c)2中的每个R4c表示氢或经任选取代的C1-C4烷基;
n为整数0或1;
Y1b,存在时,表示O、S、NR5a,其中R5a表示经任选取代的C1-C4烷基;Si(R5b)2,其中(R5b)2中的每个R5b独立地表示经任选取代的C1-C4烷基;或C(R5c)2,其中(R5c)2中的每个R5c表示氢或经任选取代的C1-C4烷基;
Y2a、Y2b、Y2c和Y2d各自独立地表示N、NR6a或CR6b,其中R6a和R6b各自独立地表示氢、经任选取代的C1-C4烷基、卤素、羟基、氨基、硝基或硫醇基;
Y3a、Y3b、Y3c、Y3d、Y3e、Y4a、Y4b、Y4c和Y4d各自独立地表示N、O、S、NR6a、CR6b,其中R6a和R6b各自独立地表示氢或经任选取代的C1-C4烷基;或Z(R6c)2,其中Z为C或Si,并且其中(R6c)2中的每个R6c独立地表示氢或经任选取代的C1-C4烷基;
其中m为整数1或2;
条件是如果m为1,Y2a和Y2d各自为CH并且Y2b或Y2c为N,则Y4a、Y4b、Y3a或Y3d中的至少一个不为N;并且
条件是如果n为0,m为2,Y2a和Y2d各自为CH并且Y2b或Y2c为N,则Y3b或Y3c中的至少一个不为N。
4.根据权利要求1所述的化合物,所述化合物由下式表示:
7.一种有机光发射二极管(OLED),所述有机光发射二极管包含作为放射性材料的由下式表示的化合物:
其中(R1)2和(R2)2中的每个R1和R2独立地表示氢、经任选取代的C1-C4烷基、卤素、羟基、氨基、硝基或硫醇基;
R3表示甲基、乙基、丙基或丁基;
Y1a表示O、S、NR4a,其中R4a表示经任选取代的C1-C4烷基;Si(R4b)2,其中(R4b)2中的每个R4b独立地表示经任选取代的C1-C4烷基;或C(R4c)2,其中(R4c)2中的每个R4c表示氢或经任选取代的C1-C4烷基;
n为整数0或1;
Y1b,存在时,表示O、S、NR5a,其中R5a表示经任选取代的C1-C4烷基;Si(R5b)2,其中(R5b)2中的每个R5b独立地表示经任选取代的C1-C4烷基;或C(R5c)2,其中(R5c)2中的每个R5c表示氢或经任选取代的C1-C4烷基;
Y2a、Y2b、Y2c和Y2d各自独立地表示N、NR61或CR6b,其中R6a和R6b各自独立地表示氢、经任选取代的C1-C4烷基、卤素、羟基、氨基、硝基或硫醇基;
Y3a、Y3b、Y3c、Y3d、Y3d、Y4a、Y4b、Y4c和Y4d各自独立地表示N、O、S、NR6a、CR6b,其中R6a和R6b各自独立地表示氢或经任选取代的C1-C4烷基;或Z(R6c)2,其中Z为C或Si,并且其中(R6c)2中的每个R6c独立地表示氢或经任选取代的C1-C4烷基;
其中m为整数1或2;
条件是如果m为1,Y2a和Y2d各自为CH并且Y2b或Y2c为N,则Y4a、Y4b、Y3a或Y3d中的至少一个不为N;并且
条件是如果n为0,m为2,Y2a和Y2d各自为CH并且Y2b或Y2c为N,则Y3b或Y3c中的至少一个不为N。
8.一种有机光伏设备,所述有机光伏设备包含作为供体或受体材料的由下式表示的化合物:
其中(R1)2和(R2)2中的每个R1和R2独立地表示氢、经任选取代的C1-C4烷基、卤素、羟基、氨基、硝基或硫醇基;
R3表示甲基、乙基、丙基或丁基;
Y1a表示O、S、NR4a,其中R4a表示经任选取代的C1-C4烷基;Si(R4b)2,其中(R4b)2中的每个R4b独立地表示经任选取代的C1-C4烷基;或C(R4c)2,其中(R4c)2中的每个R4c表示氢或经任选取代的C1-C4烷基;
n为整数0或1;
Y1b,存在时,表示O、S、NR5a,其中R5a表示经任选取代的C1-C4烷基;Si(R5b)2,其中(R5b)2中的每个R5b独立地表示经任选取代的C1-C4烷基;或C(R5c)2,其中(R5c)2中的每个R5c表示氢或经任选取代的C1-C4烷基;
Y2a、Y2b、Y2c和Y2d各自独立地表示N、NR6a或CR6b,其中R6a和R6b各自独立地表示氢、经任选取代的C1-C4烷基、卤素、羟基、氨基、硝基或硫醇基;
Y3a、Y3b、Y3c、Y3d、Y3e、Y4a、Y4b、Y4c和Y4d各自独立地表示N、O、S、NR6a、CR6b,其中R61和R6b各自独立地表示氢或经任选取代的C1-C4烷基;或Z(R6c)2,其中Z为C或Si,并且其中(R6c)2中的每个R6c独立地表示氢或经任选取代的C1-C4烷基;
其中m为整数1或2;
条件是如果m为1,Y2a和Y2d各自为CH并且Y2b或Y2c为N,则Y4a、Y4b、Y3a或Y3d中的至少一个不为N;并且
条件是如果n为0,m为2,Y2a和Y2d各自为CH并且Y2b或Y2c为N,则Y3b或Y3c中的至少一个不为N。
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WO2011137431A2 (en) | 2011-11-03 |
US20130237706A1 (en) | 2013-09-12 |
JP2013525436A (ja) | 2013-06-20 |
KR20130109947A (ko) | 2013-10-08 |
US9324957B2 (en) | 2016-04-26 |
CN102892860B (zh) | 2016-06-22 |
DE112011101527T5 (de) | 2013-05-16 |
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