CN112867709A - 作为用于oled的有机电致发光材料的5,6-二苯基-5,6-二氢-二苯并[c,e][1,2]氮杂磷杂苯和6-苯基-6h-二苯并[c,e][1,2]噻嗪-5,5-二氧化物衍生物及类似化合物 - Google Patents
作为用于oled的有机电致发光材料的5,6-二苯基-5,6-二氢-二苯并[c,e][1,2]氮杂磷杂苯和6-苯基-6h-二苯并[c,e][1,2]噻嗪-5,5-二氧化物衍生物及类似化合物 Download PDFInfo
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- CN112867709A CN112867709A CN201980068066.5A CN201980068066A CN112867709A CN 112867709 A CN112867709 A CN 112867709A CN 201980068066 A CN201980068066 A CN 201980068066A CN 112867709 A CN112867709 A CN 112867709A
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- 239000000463 material Substances 0.000 title abstract description 36
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- YQMDBOZKFVFKPJ-UHFFFAOYSA-N azaphosphinine Chemical compound C1=CC=PN=C1 YQMDBOZKFVFKPJ-UHFFFAOYSA-N 0.000 title description 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims description 121
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
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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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
- C07F9/65842—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring
- C07F9/65846—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring the phosphorus atom being part of a six-membered ring which may be condensed with another ring system
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/22—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to two ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/02—1,2-Thiazines; Hydrogenated 1,2-thiazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/36—Seven-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
- C07D291/08—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
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Abstract
本发明涉及式(1)的5,6‑二苯基‑5,6‑二氢‑二苯并[c,e][1,2]氮杂磷杂苯和6‑苯基‑6H‑二苯并[c,e][1,2]噻嗪‑5,5‑二氧化物衍生物以及类似化合物作为有机电致发光材料用于有机电致发光器件中,例如用于有机发光二极管(OLED)中,其中,对于使用的符号:Z在每种情况下相同或不同地为PAr2或S(=O);E在每种情况下相同或不同,如果E键合的符号Z代表PAr2,则所述E是O或S,并且如果E键合的符号Z代表S(=O),则所述E是O;L选自NAr2、O、S、S(=O)2、P(=O)Ar2、‑X=X‑或‑C(=O)‑NAr2;其余符号在权利要求书中定义。本发明涉及根据本发明的化合物的合成实施例、含有所述示例性化合物的OLED的制造、以及所述电致发光器件的结果。
Description
技术领域
本发明涉及用于电子器件中、尤其是用于有机电致发光器件中的材料以及涉及包含这些材料的电子器件、尤其是有机电致发光器件。
背景技术
用于有机电致发光器件(OLED)中的发光材料通常是磷光有机金属络合物。一般而言,在OLED的情况下,此外尤其是在展示出三重态发光(磷光)的OLED的情况下,例如在效率、工作电压和寿命方面仍需要改善。磷光OLED的性质不仅仅由所使用的三重态发光体决定。更特别地,所使用的其它材料例如基质材料在此也是特别重要的。
本发明的一个目的在于提供化合物,其适用于OLED中,尤其是作为磷光发光体的基质材料,而且作为电子传输材料或空穴阻挡材料,并且根据取代方式,还作为空穴传输或空穴注入或电子阻挡材料。本发明的另一目的在于提供用于有机电致发光器件的其它有机半导体,因此使本领域技术人员能够对用于制造OLED的材料有更多可行的选择。
已经令人惊奇地发现,通过下文详细描述的特定化合物实现了这个目的,所述化合物对于在OLED中使用具有良好的适合性。这些OLED尤其具有长寿命、高效率和低工作电压。因此,本发明提供这些化合物和包含该化合物的电子器件、尤其是有机电致发光器件。
WO 2011/137951公开了环状氧化膦和砜衍生物,其中磷或硫原子键合到作为环状体系例如咔唑的一部分的氮原子上。WO 2012/121398公开了氧化膦衍生物,其中磷原子键合到氮原子,其中磷原子上的两个其它取代基各自与氮原子上的两个其它取代基形成环。没有公开根据本发明的化合物。
发明内容
本发明提供一种式(1)的化合物,
其中使用的符号如下:
Z在每种情况下相同或不同并且是PAr2或S(=O);
E在每种情况下相同或不同,且当E键合的符号Z是PAr2时,所述E是O或S,并且当E键合的符号Z是S(=O)时,所述E是O;
L选自单键、NAr2、O、S、S(=O)2、P(=O)Ar2、-X=X-或-C(=O)-NAr2-;
X在每种情况下相同或不同并且是CR或N,其中每个环中不超过两个X基团是N;或者两个相邻的X是下式(2)、(3)或(4)的基团:
其中虚线键指示所述基团在式(1)中的连接;
Y在每种情况下相同或不同并且是CR或N,其中每个环中不超过两个Y基团是N;
Ar1、Ar2在每种情况下相同或不同并且是芳族或杂芳族环系,所述芳族或杂芳族环系具有5至40个芳族环原子且可被一个或多个R基团取代,其中Ar1和Ar2不彼此连接,条件是与Ar1键合的取代基R不是氟;
A在每种情况下相同或不同并且是NAr2、O、S或CR2;
V在每种情况下相同或不同并且是-NAr2-Z(=E)-;
R在每种情况下相同或不同并且是H,D,F,Cl,Br,I,N(Ar3)2,OAr3,SAr3,CN,NO2,NAr3R1,N(R1)2,OR1,SR1,COOR1,C(=O)N(R1)2,Si(R1)3,B(OR1)2,C(=O)R1,P(=O)(R1)2,S(=O)R1,S(=O)2R1,OSO2R1,具有1至20个碳原子的直链烷基基团或具有2至20个碳原子的烯基或炔基基团或具有3至20个碳原子的支链或环状的烷基基团,其中所述烷基、烯基或炔基基团在每种情况下可被一个或多个R1基团取代,其中一个或多个不相邻的CH2基团可被Si(R1)2、C=O、NR1、O、S或CONR1替换,或具有5至40个芳族环原子并且在每种情况下可被一个或多个R1基团取代的芳族或杂芳族环系;同时,两个R基团也可一起形成脂族或杂脂族环系;
Ar3在每种情况下相同或不同并且是芳族或杂芳族环系,所述芳族或杂芳族环系具有5至30个芳族环原子且可被一个或多个R1基团取代;
R1在每种情况下相同或不同并且是H,D,F,Cl,Br,I,N(R2)2,CN,NO2,OR2,SR2,Si(R2)3,B(OR2)2,C(=O)R2,P(=O)(R2)2,S(=O)R2,OSO2R2,具有1至20个碳原子的直链烷基基团或具有2至20个碳原子的烯基或炔基基团或具有3至20个碳原子的支链或环状的烷基基团,其中所述烷基、烯基或炔基基团在每种情况下可被一个或多个R2基团取代,其中一个或多个不相邻的CH2基团可被Si(R2)2、C=O、NR2、O、S或CONR2替换,或具有5至40个芳族环原子并且在每种情况下可被一个或多个R2基团取代的芳族或杂芳族环系;同时,两个或更多个R1基团可一起形成脂族环系;
R2在每种情况下相同或不同并且是H,D,F,CN,或具有1至20个碳原子的脂族、芳族或杂芳族有机基团,尤其是烃基基团,其中一个或多个氢原子也可被F替换;
其中从本发明中排除以下化合物:
在本发明的上下文中,芳基基团含有6至40个碳原子;在本发明的上下文中,杂芳基基团含有2至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和为至少5。杂原子优选选自N、O和/或S。在此,芳基基团或杂芳基基团应理解为意指简单的芳族环,即苯,或简单的杂芳族环,例如吡啶、嘧啶、噻吩等,或缩合(稠合)的芳基或杂芳基基团,例如萘、蒽、菲、喹啉、异喹啉等。相反,通过单键彼此连接的芳族体系,例如联苯,不是芳基或杂芳基基团,而是芳族环系。
在本发明的上下文中,芳族环系在环系中含有6至40个碳原子。在本发明的上下文中,杂芳族环系在环系中含有2至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和为至少5。杂原子优选选自N、O和/或S。在本发明的上下文中,芳族或杂芳族环系应理解为意指以下体系,其不必仅含有芳基或杂芳基基团,而是其中两个或更多个芳基或杂芳基基团也可通过非芳族单元例如碳、氮或氧原子连接。这些同样应理解为意指其中两个或更多个芳基或杂芳基基团彼此直接连接的体系,例如联苯、三联苯、联吡啶或苯基吡啶。例如,在本发明的上下文中,例如芴、9,9’-螺二芴、9,9-二芳基芴、三芳基胺、二芳基醚、茋等的体系也应被视为芳族环系,并且其中两个或更多个芳基基团例如通过短的烷基基团连接的体系也是如此。优选的芳族或杂芳族环系是简单的芳基或杂芳基基团和其中两个或更多个芳基或杂芳基基团彼此直接连接的基团,例如联苯或联吡啶,以及芴或螺二芴。
在本发明的上下文中,可含有1至40个碳原子并且其中个别氢原子或CH2基团也可被上述基团取代的脂族烃基基团或烷基或烯基或炔基基团,优选应理解为意指甲基、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、新戊基、环戊基、正己基、新己基、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、庚炔基或辛炔基基团。具有1至40个碳原子的烷氧基基团OR1优选应理解为意指甲氧基、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、正戊氧基、仲戊氧基、2-甲基丁氧基、正己氧基、环己氧基、正庚氧基、环庚氧基、正辛氧基、环辛氧基、2-乙基己氧基、五氟乙氧基和2,2,2-三氟乙氧基。具有1至40个碳原子的硫代烷基基团SR1应理解为尤其意指甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、正戊硫基、仲戊硫基、正己硫基、环己硫基、正庚硫基、环庚硫基、正辛硫基、环辛硫基、2-乙基己硫基、三氟甲硫基、五氟乙硫基、2,2,2-三氟乙硫基、乙烯硫基、丙烯硫基、丁烯硫基、戊烯硫基、环戊烯硫基、己烯硫基、环己烯硫基、庚烯硫基、环庚烯硫基、辛烯硫基、环辛烯硫基、乙炔硫基、丙炔硫基、丁炔硫基、戊炔硫基、己炔硫基、庚炔硫基或辛炔硫基。通常,根据本发明的烷基、烷氧基或硫代烷基基团可以是直链、支链或环状的,其中一个或多个不相邻的CH2基团可被上述基团替换;另外,一个或多个氢原子还可被D、F、Cl、Br、I、CN或NO2替换,优选被F、Cl或CN替换,更优选被F或CN替换。
具有5至60个芳族环原子并且在每种情况下也可被上述R2基团或烃基基团取代并且可通过任何所需位置连接到所述芳族或杂芳族体系的芳族或杂芳族环系,应理解为尤其意指衍生自以下物质的基团:苯、萘、蒽、苯并蒽、菲、芘、苣、苝、荧蒽、并四苯、并五苯、苯并芘、联苯、联二苯叉、三联苯、联三苯叉、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式或反式茚并芴、顺式或反式茚并咔唑、顺式或反式吲哚并咔唑、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、唑、苯并唑、萘并唑、蒽并唑、菲并唑、异唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、六氮杂联三苯叉、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、吩嗪、吩噻嗪、荧红环、萘啶、氮杂咔唑、苯并咔啉、菲咯啉、1,2,3-***、1,2,4-***、苯并***、1,2,3-二唑、1,2,4-二唑、1,2,5-二唑、1,3,4-二唑、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、喋啶、吲哚嗪和苯并噻二唑,或由这些体系的组合衍生的基团。
在本说明书的上下文中,两个或更多个基团可一起形成环的措辞应理解为尤其意指这两个基团通过化学键彼此连接,形式上消除了两个氢原子。这通过以下方案说明:
然而,另外,上述措辞还应该理解为意指,如果两个基团中的一个是氢,则第二个基团键合到氢原子所键合的位置,从而形成环。这将通过以下方案说明:
在本发明的一个实施方式中,式(1)的化合物不包含任何式(2)、(3)或(4)的基团,使得所述化合物为下式(1-1)中的一种:
其中X在每种情况下相同或不同并且是CR或N,其中每个环中不超过两个X基团是N,并且其它的符号具有上面给出的定义。
当化合物含有式(2)、(3)或(4)的基团时,根据键的位置产生不同的异构体。对于式(1)的化合物和式(2)的基团,这些例如在下面由式(5)至(16)显示:
其中X具有上面给出的定义,并且优选在每种情况下相同或不同并且是CR或N,其中每个环中不超过两个X基团是N,并且其它的符号具有上面给出的定义。
对于式(3)和(4)的稠合基团,类似地得到相应的结构。
在本发明的一个优选的实施方式中,在式(2)、(3)或(4)的基团中,不超过一个符号Y是N,并且其它符号Y相同或不同并且是CR。更优选地,式(2)、(3)和(4)中的所有符号Y都是CR,使得所述基团优选分别是式(2a)、(3a)和(4a)中的一种:
其中使用的符号具有上面给出的定义。
在式(2)或(2a)或式(5)至(16)和下式中的一个优选的实施方式中,A在每种情况下相同或不同且为NAr2。
在本发明的一个优选的实施方式中,式(1)的化合物不含式(2)、(3)或(4)的基团,或总共含有一个或两个式(2)、(3)或(4)的基团,优选每个环中连接不超过一个式(2)、(3)或(4)的基团。更优选地,式(1)的化合物不含或含有一个式(2)、(3)或(4)的基团。不为式(2)、(3)或(4)的基团的其余符号X在每种情况下相同或不同,并且是CR或N。最优选地,式(1)的化合物不含任何式(2)、(3)或(4)的基团,并且符号X相同或不同并且是CR或N。
在本发明的另一个优选的实施方式中,式(1)的每个环中不超过一个符号X是N,并且更优选地总共不超过一个符号X是N。最优选地,不为式(2)、(3)或(4)的基团的符号X在每种情况下相同或不同并且是CR。在本发明的一个特别优选的实施方式中,符号Y在每种情况下相同或不同并且是CR,使得所述基团优选是式(2a)、(3a)或(4a)中的一种,并且不为式(2a)、(3a)或(4a)的基团的符号X在每种情况下相同或不同并且是CR。
因此,式(1)的优选实施方式是下式(1a)和(5a)至(16a)的结构:
其中使用的符号具有上面给出的定义。A在此优选是NAr2。
在式(1)和上面详述的本发明的优选实施方式中,E优选是O。
在本发明的一个实施方式中,L是单键,与L相邻键合的R基团是P(=O)R1或S(=O)2R1,并且与L相邻键合的另一个R基团是N(Ar3)R1,其中这两个R基团一起形成环。这产生下式(17)和(18)的结构,以及优选的实施方式(17a)和(18a):
其中使用的符号具有上面给出的定义并且Z1是PR1或S(=O)。E在此优选是O,并且键合到Z1的R1基团优选是芳族或杂芳族环系,所述芳族或杂芳族环系具有6至30个芳族环原子,优选6至13个芳族环原子,并且可被一个或多个R2基团取代。
在本发明的一个优选的实施方式中,在式(1)的化合物或上面详述的优选结构中,总共不超过三个R基团,更优选不超过两个R基团且最优选不超过一个R基团是不为氢的基团。
特别优选给出下式(1b)或(5b)至(16b)的结构:
其中使用的符号具有上面给出的定义。
在本发明的一个优选的实施方式中,Z在每种情况下相同或不同并且是PAr2。
在本发明的另一个优选的实施方式中,E是O。
在本发明的另一个优选的实施方式中,L是单键、NAr2、O、S、S(=O)2或-CR=CR-,更优选是单键、NAr2或O,且最优选是单键。
在本发明的一个特别优选的实施方式中,Z是PAr2,且E是O,并且L是单键。因此,特别优选的是下式(1c)和(5c)至(16c)的化合物:
其中使用的符号具有上面给出的定义。A在此优选是NAr2。R基团优选在类似于式(1b)和(5b)至(16b)的结构的位置上键合。
下面描述优选的取代基Ar1、Ar2、R、Ar3、R1和R2。在本发明的一个特别优选的实施方式中,上面对X、Y、Z、E和L指明的优选方式和下文对Ar1、Ar2、R、Ar3、R1和R2指明的优选方式同时存在,并且适用于式(1)的结构和上面详述的所有优选的实施方式。
在本发明的一个优选的实施方式中,Ar1和Ar2在每种情况下相同或不同,并且是芳族或杂芳族环系,所述芳族或杂芳族环系具有6至30个芳族环原子且可被一个或多个R基团取代,其中在Ar1的情况下,R基团不是氟。更优选地,Ar1和Ar2在每种情况下相同或不同,并且是芳族或杂芳族环系,所述芳族或杂芳族环系具有6至24个芳族环原子,尤其是6至12个芳族环原子,并且可被一个或多个优选非芳族R基团取代,其中在Ar1的情况下,R基团不是氟。当Ar是杂芳基基团,尤其是三嗪、嘧啶、喹唑啉或咔唑时,所述杂芳基基团上的芳族或杂芳族取代基R也可以取优选方式。还可优选的是Ar1或Ar2被N(Ar3)2基团取代,使得取代基Ar1或Ar2总体上构成三芳基胺或三杂芳基胺基团。
合适的芳族或杂芳族环系Ar1或Ar2在每种情况下相同或不同,并且选自:苯基;联苯,尤其是邻-、间-或对-联苯;三联苯,尤其是邻-、间-或对-三联苯或支链三联苯;四联苯,尤其是邻-、间-或对-四联苯或支链四联苯;可经由1、2、3或4位连接的芴;可经由1、2、3或4位连接的螺二芴;可经由1或2位连接的萘;吲哚;苯并呋喃;苯并噻吩;可经由1、2、3或4位连接的咔唑;可经由1、2、3或4位连接的二苯并呋喃;可经由1、2、3或4位连接的二苯并噻吩;茚并咔唑;吲哚并咔唑;吡啶;嘧啶;吡嗪;哒嗪;三嗪;喹啉;喹唑啉;苯并咪唑;菲;联三苯叉或这些基团中的两个或三个的组合,其各自可被一个或多个R基团,优选非芳族R基团取代。当Ar是杂芳基基团,尤其是三嗪、嘧啶、喹唑啉或咔唑时,所述杂芳基基团上的芳族或杂芳族R基团也可以取优选方式。
Ar1和Ar2在此在每种情况下优选相同或不同且选自下式Ar-1至Ar-76的基团:
其中R具有上面给出的定义,并且在Ar1上的取代基的情况下不是氟,在Ar1的情况下,虚线键表示与氮原子键合的键,并且在Ar2的情况下,虚线键表示与磷或氮原子键合的键,并且另外:
Ar’在每种情况下相同或不同,并且是二价芳族或杂芳族环系,所述二价芳族或杂芳族环系具有6至18个芳族环原子,优选6至13个芳族环原子,并且在每种情况下可被一个或多个R基团取代;
A在每种情况下相同或不同并且是CR2、NR、O或S;
n为0或1,其中n=0意指在所述位置未键合A基团,而是R基团键合到相应的碳原子;
m为0或1,其中m=0意指Ar’基团不存在且相应的芳族或杂芳族基团直接键合到氮原子或磷原子。
在本发明的一个优选的实施方式中,R在每种情况下相同或不同并且选自H,D,F,N(Ar3)2,CN,OR1,具有1至10个碳原子的直链烷基基团或具有2至10个碳原子的烯基基团或具有3至10个碳原子的支链或环状的烷基基团,其中所述烷基或烯基基团各自可被一个或多个R1基团取代,但优选是未取代的,并且其中一个或多个不相邻的CH2基团可被O替换,或具有6至30个芳族环原子且在每种情况下可被一个或多个R1基团取代的芳族或杂芳族环系;同时,两个R基团也可一起形成脂族环系。更优选地,R在每种情况下相同或不同,并且选自H,N(Ar3)2,具有1至6个碳原子,尤其具有1、2、3或4个碳原子的直链烷基基团或具有3至6个碳原子的支链或环状的烷基基团,其中所述烷基基团在每种情况下可被一个或多个R1基团取代,但优选是未取代的,或芳族或杂芳族环系,所述芳族或杂芳族环系具有6至24个芳族环原子且在每种情况下可被一个或多个R1基团、优选非芳族R1基团取代。最优选地,R在每种情况下相同或不同,并且选自H或芳族或杂芳族环系,所述芳族或杂芳族环系具有6至24个芳族环原子,更优选6至13个芳族环原子,并且在每种情况下可被一个或多个R1基团、优选非芳族R1基团取代。另外可优选的是,R是可被一个或多个R1基团取代的三芳基胺基团或三杂芳基胺基团。所述基团是芳族或杂芳族环系的一个实施方式,在这种情况下,两个或更多个芳基或杂芳基基团通过氮原子彼此连接。当R是三芳基胺基团或三杂芳基胺基团时,所述基团优选具有18至30个芳族环原子并且可被一个或多个R1基团、优选非芳族R1基团取代。
在本发明的另一个优选的实施方式中,Ar3是芳族或杂芳族环系,所述芳族或杂芳族环系具有6至24个芳族环原子,更优选6至13个芳族环原子,并且可被一个或多个优选非芳族R1基团取代。
在本发明的另一个优选的实施方式中,R1在每种情况下相同或不同,并且选自H,D,F,CN,OR2,具有1至10个碳原子的直链烷基基团或具有2至10个碳原子的烯基基团或具有3至10个碳原子的支链或环状的烷基基团,其中所述烷基或烯基基团在每种情况下可被一个或多个R2基团取代,并且其中一个或多个不相邻的CH2基团可被O替换,或具有6至30个芳族环原子且在每种情况下可被一个或多个R2基团取代的芳族或杂芳族环系;同时,两个或更多个R1基团可一起形成脂族环系。在本发明的一个特别优选的实施方式中,R1在每种情况下相同或不同,并且选自H,具有1至6个碳原子,尤其具有1、2、3或4个碳原子的直链烷基基团或具有3至6个碳原子的支链或环状的烷基基团,其中所述烷基基团可被一个或多个R2基团取代,但优选是未取代的,或芳族或杂芳族环系,所述芳族或杂芳族环系具有6至24个芳族环原子,优选6至13个芳族环原子,且在每种情况下可被一个或多个R2基团取代,但优选是未取代的。
在本发明的另一个优选的实施方式中,R2在每种情况下相同或不同,并且是H,F,具有1至4个碳原子的烷基基团或具有6至10个碳原子的芳基基团,所述芳基基团可被具有1至4个碳原子的烷基基团取代,但优选是未取代的。
合适的芳族或杂芳族环系R或Ar3选自:苯基;联苯,尤其是邻-、间-或对-联苯;三联苯,尤其是邻-、间-或对-三联苯或支链三联苯;四联苯,尤其是邻-、间-或对-四联苯或支链四联苯;可经由1、2、3或4位连接的芴;可经由1、2、3或4位连接的螺二芴;可经由1或2位连接的萘;吲哚;苯并呋喃;苯并噻吩;可经由1、2、3或4位连接的咔唑;可经由1、2、3或4位连接的二苯并呋喃;可经由1、2、3或4位连接的二苯并噻吩;茚并咔唑;吲哚并咔唑;吡啶;嘧啶;吡嗪;哒嗪;三嗪;喹啉;喹唑啉;苯并咪唑;菲;联三苯叉或这些基团中的两个或三个的组合,其各自可被一个或多个R1基团取代。当R或Ar3是杂芳基基团,尤其是三嗪、嘧啶、喹唑啉或咔唑时,所述杂芳基基团上的芳族或杂芳族R1基团也可以取优选方式。
在此,R基团(当它们是芳族或杂芳族环系时)或Ar3优选选自下式R-1至R-76的基团:
其中R1如上所定义,虚线键表示所述基团的连接,并且另外:
Ar’在每种情况下相同或不同,并且是具有6至18个芳族环原子并且在每种情况下可被一个或多个R1基团取代的二价芳族或杂芳族环系;
A在每种情况下相同或不同并且是C(R1)2、NR1、O或S;
n为0或1,其中n=0意指在所述位置未键合A基团,而是R1基团键合到相应的碳原子;
m为0或1,其中m=0意指Ar3基团不存在且相应的芳族或杂芳族基团直接键合到式(1)或优选实施方式中的基础骨架的碳原子,或键合到Ar1或Ar2,或键合到N(Ar3)2基团中的氮原子;条件是对于结构(R-12)、(R-17)、(R-21)、(R-25)、(R-26)、(R-30)、(R-34)、(R-38)和(R-39),当这些基团是Ar3的实施方式时,m=1。
当在Ar1或Ar2的情况下的上述Ar-1至Ar-76基团或在R或Ar3的情况下的R-1至R-76基团具有两个或更多个A基团时,这些的可行选择包括来自A定义的所有组合。在那种情况下的优选实施方式是如下实施方式:其中一个A基团是NR或NR1,而另一个A基团是C(R)2或C(R1)2,或者其中两个A基团都是NR或NR1,或者其中两个A基团都是O。在本发明的一个特别优选的实施方式中,在具有两个或更多个A基团的Ar1、Ar2、R或Ar3基团中,至少一个A基团是C(R)2或C(R1)2或者是NR或NR1。
当在式(2)或式(2a)中或在式Ar-1至Ar-76中或在式R-1至R-76中的A是NR或NR1时,键合到氮原子的取代基R或R1优选是芳族或杂芳族环系,所述芳族或杂芳族环系具有5至24个芳族环原子并且还可被一个或多个R1或R2基团取代。在一个特别优选的实施方式中,所述R或R1取代基在每种情况下相同或不同,并且是芳族或杂芳族环系,所述芳族或杂芳族环系具有6至24个芳族环原子,优选6至12个芳族环原子,并且其不具有其中两个或更多个芳族或杂芳族6-元环基团彼此直接稠合的任何稠合芳基基团或杂芳基基团,并且其在每种情况下也可被一个或多个R1或R2基团取代。特别优选的是具有如上面对于Ar-1至Ar-11或R-1至R-11所列的键合方式的苯基、联苯、三联苯和四联苯,其中这些结构可被一个或多个R1或R2基团取代,但优选是未取代的。
当在式(2)或式(2a)中或在式Ar-1至Ar-76中或在式R-1至R-76中的A为C(R)2或C(R1)2时,键合到所述碳原子上的取代基R或R1优选在每种情况下相同或不同,并且是具有1至10个碳原子的直链烷基基团或具有3至10个碳原子的支链或环状的烷基基团或具有5至24个芳族环原子并且还可被一个或多个R1或R2基团取代的芳族或杂芳族环系。最优选地,R或R1是甲基基团或苯基基团。在这种情况下,R或R1基团也可一起形成环系,这产生螺环系。
另外合适的Ar1、Ar2、R或Ar’基团是式-Ar4-N(Ar5)(Ar6)的基团,其中Ar4、Ar5和Ar6在每种情况下相同或不同,并且是具有5至24个芳族环原子并且在每种情况下可被一个或多个R1基团取代的芳族或杂芳族环系。当Ar1或Ar2基团被N(Ar3)2基团取代时,Ar1或Ar2产生这样的基团。Ar4、Ar5和Ar6中的芳族环原子的总数在此不大于60,且优选不大于40。
在这种情况下,Ar4和Ar5也可经由选自C(R1)2、NR1、O或S的基团彼此键合和/或Ar5和Ar6也可经由选自C(R1)2、NR1、O或S的基团彼此键合。优选地,Ar4和Ar5在与氮原子键合的相应邻位上彼此连接,并且Ar5和Ar6在与氮原子键合的相应邻位上彼此连接。在本发明的另一个实施方式中,Ar4、Ar5和Ar6基团中没有一个彼此键合。
优选地,Ar4是芳族或杂芳族环系,所述芳族或杂芳族环系具有6至24个芳族环原子,尤其是6至12个芳族环原子并且在每种情况下可被一个或多个R1基团取代。更优选地,Ar4选自邻-、间-或对-苯亚基或者邻-、间-或对-联苯,其各自可被一个或多个R1基团取代,但优选是未取代的。最优选地,Ar4是未取代的苯亚基基团。
优选地,Ar5和Ar6在每种情况下相同或不同,并且是具有6至24个芳族环原子并且在每种情况下可被一个或多个R1基团取代的芳族或杂芳族环系。特别优选的Ar5和Ar6基团在每种情况下相同或不同,并且选自苯,邻-、间-或对-联苯,邻-、间-或对-三联苯或支链三联苯,邻-、间-或对-四联苯或支链四联苯,1-、2-、3-或4-芴基,1-、2-、3-或4-螺二芴基,1-或2-萘基,吲哚,苯并呋喃,苯并噻吩,1-、2-、3-或4-咔唑,1-、2-、3-或4-二苯并呋喃,1-、2-、3-或4-二苯并噻吩,茚并咔唑,吲哚并咔唑,2-、3-或4-吡啶,2-、4-或5-嘧啶,吡嗪,哒嗪,三嗪,菲,联三苯叉,或这些基团中的两个、三个或四个的组合,其各自可被一个或多个R1基团取代。更优选地,Ar5和Ar6在每种情况下相同或不同,并且是芳族环系,所述芳族环系具有6至24个芳族环原子并且可被一个或多个R1基团取代,尤其选自苯,联苯,尤其是邻-、间-或对-联苯,三联苯,尤其是邻-、间-或对-三联苯或支链三联苯,四联苯,尤其是邻-、间-或对-四联苯或支链四联苯,芴,尤其是1-、2-、3-或4-芴,或螺二芴,尤其是1-、2-、3-或4-螺二芴。
同时,通过真空蒸发加工的化合物中的烷基基团优选具有不超过5个碳原子,更优选不超过4个碳原子,最优选不超过1个碳原子。对于自溶液加工的化合物,合适的化合物也是被具有至多10个碳原子的烷基基团,尤其是支链烷基基团取代的那些化合物,或被低聚芳亚基基团,例如邻-、间-或对-三联苯或支链三联苯或者四联苯基团取代的那些化合物。
当式(1)或优选的实施方式的化合物用作磷光发光体的基质材料或在直接邻接磷光层的层中使用时,优选的是所述化合物不含其中超过两个六元环直接彼此稠合的任何稠合的芳基或杂芳基基团。对此的例外是由菲和联三苯叉形成的,尽管存在稠合的芳族六元环,但它们由于高的三重态能量而可以是优选的。
在权利要求1限定的限制内,上述优选的实施方式可根据需要彼此组合。在本发明的一个特别优选的实施方式中,上述优选方式同时适用。
根据上述具体实施方式的合适化合物的实例是下面列出的化合物。
本发明的化合物可根据以下方案合成。方案1至4显示其中Z=PAr2的化合物的合成,并且方案5显示其中Z=S(=O)的化合物的合成。所引用的参考文献描述了例如对于在氮上具有烷基而不是芳基或杂芳基的化合物的类似反应。
方案1:
方案2:
方案3:
方案4:
方案5:
为了从液相中例如通过旋涂或印刷方法加工本发明的化合物,需要本发明的化合物的制剂。这些制剂可以是例如溶液、分散体或乳液。为此目的,可优选使用两种或更多种溶剂的混合物。合适且优选的溶剂例如是甲苯,苯甲醚,邻-、间-或对-二甲苯,苯甲酸甲酯,均三甲苯,四氢化萘,藜芦醚,THF,甲基-THF,THP,氯苯,二烷,苯氧基甲苯、尤其是3-苯氧基甲苯,(-)-葑酮,1,2,3,5-四甲基苯,1,2,4,5-四甲基苯,1-甲基萘,2-甲基苯并噻唑,2-苯氧基乙醇,2-吡咯烷酮,3-甲基苯甲醚,4-甲基苯甲醚,3,4-二甲基苯甲醚,3,5-二甲基苯甲醚,苯乙酮,α-萜品醇,苯并噻唑,苯甲酸丁酯,异丙苯,环己醇,环己酮,环己基苯,十氢化萘,十二烷基苯,苯甲酸乙酯,茚满,NMP,对伞花烃,苯***,1,4-二异丙基苯,二苄基醚,二乙二醇丁基甲基醚,三乙二醇丁基甲基醚,二乙二醇二丁基醚,三乙二醇二甲醚,二乙二醇单丁醚,三丙二醇二甲醚,四乙二醇二甲醚,2-异丙基萘,戊基苯,己基苯,庚基苯,辛基苯,1,1-双(3,4-二甲基苯基)乙烷,2-甲基联苯,3-甲基联苯,1-甲基萘,1-乙基萘,辛酸乙酯,癸二酸二乙酯,辛基辛酯,庚基苯,异戊酸薄荷酯,己酸环己酯,或这些溶剂的混合物。
因此,本发明还提供一种包含本发明的化合物和至少一种其它化合物的制剂。所述其它化合物可以是例如溶剂,尤其是上述溶剂中的一种或这些溶剂的混合物。所述其它化合物可以可选地是至少一种同样用于电子器件中的其它的有机或无机化合物,例如发光化合物和/或其它的基质材料。合适的发光化合物和其它的基质材料在后面结合有机电致发光器件列出。所述其它化合物也可以是聚合的。
本发明的化合物适用于电子器件,尤其是有机电致发光器件中。
因此,本发明还提供本发明的化合物在电子器件中、尤其是在有机电致发光器件中的用途。
本发明再进一步提供一种包含至少一种本发明的化合物的电子器件。
在本发明的上下文中,电子器件是包括至少一个包含至少一种有机化合物的层的器件。这种组件也可包含无机材料或者完全由无机材料形成的层。
电子器件优选选自有机电致发光器件(OLED)、有机集成电路(O-IC)、有机场效应晶体管(O-FET)、有机薄膜晶体管(O-TFT)、有机发光晶体管(O-LET)、有机太阳能电池(O-SC)、染料敏化的有机太阳能电池(DSSC)、有机光学检测器、有机光感受器、有机场猝熄器件(O-FQD)、发光电化学电池(LEC)、有机激光二极管(O-laser)和有机等离子体发光器件,但优选有机电致发光器件(OLED),更优选磷光OLED。
所述有机电致发光器件包含阴极、阳极和至少一个发光层。除了这些层之外,其还可包含另外的层,例如在每种情况下,一个或多个空穴注入层、空穴传输层、空穴阻挡层、电子传输层、电子注入层、激子阻挡层、电子阻挡层和/或电荷产生层。例如,具有激子阻挡功能的夹层同样可被引入两个发光层之间。然而,应该指出,这些层中的每一个不必都存在。在这种情况下,有机电致发光器件可以包括发光层,或者包括多个发光层。如果存在多个发光层,则这些发光层优选具有总共多个380nm至750nm的发光最大值,使得总体结果是白色发光;换句话说,在发光层中使用可发荧光或磷光的多种发光化合物。尤其优选的是具有三个发光层的体系,其中这三层显示蓝色、绿色和橙色或红色发光。本发明的有机电致发光器件也可以是串联OLED,尤其是发白光的OLED。
根据确切的结构,根据上面的具体实施方式的本发明的化合物可用于不同的层中。优选的是包含在发光层中作为磷光发光体或表现出TADF(热活化的延迟荧光)的发光体,尤其是磷光发光体的基质材料的式(1)的化合物或上面列举的优选实施方式的有机电致发光器件。在这种情况下,有机电致发光器件可包括发光层,或者其可包括多个发光层,其中至少一个发光层含有至少一种本发明的化合物作为基质材料。另外,本发明的化合物还可用于电子传输层和/或空穴阻挡层和/或空穴传输层和/或激子阻挡层中。
当本发明的化合物用作发光层中的磷光化合物的基质材料时,其优选与一种或多种磷光材料(三重态发光体)组合使用。在本发明的上下文中,磷光应理解为意指来自具有较高自旋多重性,即自旋态>1的激发态、尤其是来自激发的三重态的发光。在本申请的上下文中,具有过渡金属或镧系元素的所有发光络合物,尤其是所有铱、铂和铜络合物都应被认为是磷光化合物。
基于发光体与基质材料的总混合物,本发明的化合物与发光化合物的混合物含有99体积%至1体积%、优选98体积%至10体积%、更优选97体积%至60体积%且尤其是95体积%至80体积%的本发明的化合物。相应地,基于发光体与基质材料的总混合物,所述混合物含有1体积%至99体积%、优选2体积%至90体积%、更优选3体积%至40体积%且尤其是5体积%至20体积%的发光体。
本发明的另一个优选的实施方式是本发明的化合物作为磷光发光体的基质材料与其它基质材料组合的用途。可与本发明化合物组合使用的合适基质材料是芳族酮、芳族氧化膦或芳族亚砜或砜,例如根据WO 2004/013080、WO 2004/093207、WO 2006/005627或WO2010/006680的;三芳基胺、咔唑衍生物,例如CBP(N,N-双咔唑基联苯)或咔唑衍生物,在WO2005/039246、US 2005/0069729、JP 2004/288381、EP 1205527、WO 2008/086851或WO2013/041176中公开的;吲哚并咔唑衍生物,例如根据WO 2007/063754或WO 2008/056746的;茚并咔唑衍生物,例如根据WO 2010/136109、WO 2011/000455、WO 2013/041176或WO2013/056776的;氮杂咔唑衍生物,例如根据EP 1617710、EP 1617711、EP 1731584、JP2005/347160的;双极基质材料,例如根据WO 2007/137725的;硅烷,例如根据WO 2005/111172的;硼氮杂环戊熳或硼酸酯,例如根据WO 2006/117052的;三嗪衍生物,例如根据WO2007/063754、WO 2008/056746、WO 2010/015306、WO 2011/057706、WO 2011/060859或WO2011/060877的;锌络合物,例如根据EP 652273或WO 2009/062578的;硅二氮杂环戊熳或硅四氮杂环戊熳,例如根据WO 2010/054729的;磷二氮杂环戊熳衍生物,例如根据WO 2010/054730的;桥联的咔唑衍生物,例如根据WO 2011/042107、WO 2011/060867、WO 2011/088877和WO 2012/143080的;联三苯叉衍生物,例如根据WO 2012/048781的;或二苯并呋喃衍生物,例如根据WO 2015/169412、WO 2016/015810、WO 2016/023608、WO 2017/148564或WO 2017/148565的。具有比实际发光体短的波长发光的其它磷光发光体同样可以作为共主体存在于混合物中,或者即使参与电荷传输但未在显著程度上参与电荷传输的化合物,如在例如WO 2010/108579中所述的。
尤其适合与本发明的化合物组合作为共基质材料的是具有大带隙并且自身即使参与电荷传输但至少不在显著程度上参与发光层的电荷传输的化合物。这类材料优选是纯烃。这类材料的实例可例如在WO 2006/130598、WO 2009/021126、WO 2009/124627和WO2010/006680中见到。
在本发明的一个优选的实施方式中,所述材料与其它的基质材料组合使用。优选的共基质材料选自联咔唑、桥联咔唑、三芳基胺、二苯并呋喃-咔唑衍生物或二苯并呋喃-胺衍生物、咔唑胺和三嗪衍生物。
优选的联咔唑是下式(19)和(20)的结构:
其中Ar2和A具有上面给出的定义,并且R具有上面给出的定义,但R基团在此也可一起形成芳族或杂芳族环系。在本发明的一个优选的实施方式中,A是CR2。
式(19)和(20)的化合物的优选实施方式是下式(19a)和(20a)的化合物:
其中使用的符号具有上面给出的定义。
合适的式(19)和(20)的化合物的实例是下面描绘的基团:
优选的桥联咔唑是下式(21)的结构:
其中A和R具有上面给出的定义,并且A在每种情况下优选相同或不同,并且选自NAr2和CR2。
式(21)的一个优选的实施方式是式(21a)的化合物,特别优选式(21b)的化合物,并且非常特别优选式(21c)的化合物
其中Ar2和R具有上面给出的定义。Ar2在此在每种情况下优选相同或不同,并且是具有6至18个芳族环原子的芳族环系,例如苯基,邻-、间-或对-联苯或三联苯。茚碳原子上的R基团在每种情况下优选相同或不同,并且是具有1至5个碳原子的烷基基团,尤其是甲基基团,或具有6至18个芳族环原子的芳族环系,尤其是苯基。
优选的三芳基胺是下式(22)的结构:
其中Ar2具有上面给出的定义。
优选的二苯并呋喃衍生物是下式(23)的化合物:
其中氧也可被硫替换以形成二苯并噻吩,L1是单键或芳族或杂芳族环系,所述芳族或杂芳族环系具有5至30个芳族环原子并且也可被一个或多个R基团取代,并且R和Ar2具有上面给出的定义。在此也可行的是,与同一氮原子键合的两个Ar2基团,或与同一氮原子键合的一个Ar2基团和一个L1基团彼此键合,例如得到咔唑。
式(23)的化合物的优选实施方式是下式(23a)和(23b)的化合物:
其中氧也可被硫替换以形成二苯并噻吩,并且R和Ar2具有上面给出的定义,其中两个相邻的R基团,尤其是在咔唑上的两个相邻的R基团,在此也可一起形成芳族或杂芳族环系。
特别优选的实施方式是下式(23c)和(23d)的化合物:
其中氧也可被硫替换以形成二苯并噻吩,并且Ar2具有上面给出的定义,其中两个相邻的R基团,尤其是在咔唑上的两个相邻的R基团,在此也可一起形成芳族或杂芳族环系。
合适的二苯并呋喃衍生物的实例是下面描绘的化合物。
优选的咔唑胺是下式(24)、(25)和(26)的结构:
其中L1是芳族或杂芳族环系,所述芳族或杂芳族环系具有5至30个芳族环原子且可被一个或多个R基团取代,并且R和Ar2具有上面给出的定义,其中两个相邻的R基团在此也可形成芳族环系。
合适的咔唑胺衍生物的实例是下面描绘的化合物。
可与本发明的化合物一起作为混合物使用的优选三嗪或嘧啶衍生物是下式(27)和(28)的化合物:
其中Ar2具有上面给出的定义。上面详述的Ar2的优选实施方式在此也适用于式(27)和(28)的化合物。特别优选的是式(27)的三嗪衍生物。
可与本发明的化合物一起用作基质材料的三嗪衍生物的实例是下面列出的化合物:
合适的磷光化合物(=三重态发光体)尤其是如下化合物,其在被合适地激发时发射优选在可见光区的光,并且还含有至少一个原子序数大于20,优选大于38且小于84,更优选大于56且小于80的原子,尤其是具有所述原子序数的金属。使用的优选磷光发光体是含有铜、钼、钨、铼、钌、锇、铑、铱、钯、铂、银、金或铕的化合物,尤其是含有铱或铂的化合物。
上述发光体的实例可在申请WO 00/70655、WO 2001/41512、WO 2002/02714、WO2002/15645、EP 1191613、EP 1191612、EP 1191614、WO 05/033244、WO 05/019373、US2005/0258742、WO 2009/146770、WO 2010/015307、WO 2010/031485、WO 2010/054731、WO2010/054728、WO 2010/086089、WO 2010/099852、WO 2010/102709、WO 2011/032626、WO2011/066898、WO 2011/157339、WO 2012/007086、WO 2014/008982、WO 2014/023377、WO2014/094961、WO 2014/094960、WO 2015/036074、WO 2015/104045、WO 2015/117718、WO2016/015815、WO 2016/124304、WO 2017/032439、WO 2018/011186和WO 2018/041769、WO2019/020538、WO 2018/178001、WO 2019/115423以及尚未公开的专利申请EP 18156388.3中见到。通常,如根据现有技术用于磷光OLED并且如有机电致发光领域的技术人员已知的所有磷光络合物都是合适的,并且本领域技术人员能够在不付出创造性劳动的情况下使用其它的磷光络合物。
下面举出磷光掺杂剂的实例。
本发明的化合物也适合作为有机电致发光器件中的磷光发光体的基质材料,如在例如WO 98/24271、US 2011/0248247和US 2012/0223633中所述的。在这些多色显示组件中,通过在整个区域上气相沉积将附加的蓝色发光层施用到所有像素,包括具有除蓝色外的颜色的那些像素。
在本发明的另一个实施方式中,本发明的有机电致发光器件不包括任何单独的空穴注入层和/或空穴传输层和/或空穴阻挡层和/或电子传输层,意味着发光层与空穴注入层或阳极直接邻接,和/或发光层与电子传输层或电子注入层或阴极直接邻接,如在例如WO2005/053051中所述的。另外地,可以使用与发光层中的金属络合物相同或类似的金属络合物作为与发光层直接邻接的空穴传输或空穴注入材料,如在例如WO 2009/030981中所述的。
在本发明的有机电致发光器件的其它层中,可以使用如根据现有技术通常使用的任何材料。因此,本领域技术人员将能够在不付出创造性劳动的情况下将已知用于有机电致发光器件的任何材料与式(1)或(2)的本发明化合物或上面列举的优选实施方式组合使用。
另外优选的是一种有机电致发光器件,其特征在于通过升华工序涂覆一层或多层。在这种情况下,材料在真空升华***中在小于10-5mbar、优选小于10-6mbar的初始压力下通过气相沉积施用。然而,初始压力也可以甚至更低,例如小于10-7mbar。
同样优选的是一种有机电致发光器件,其特征在于一层或多层是通过OVPD(有机气相沉积)方法或借助于载气升华涂覆的。在这种情况下,材料是在10-5mbar和1bar之间的压力下施用的。所述方法的一个特例是OVJP(有机蒸气喷射印刷)方法,其中材料通过喷嘴直接施用并因此结构化。
另外优选的是一种有机电致发光器件,其特征在于一层或多层是从溶液中例如通过旋涂,或通过任何印刷方法如丝网印刷、柔版印刷、胶版印刷、LITI(光诱导热成像、热转移印刷)、喷墨印刷或喷嘴印刷制造的。为此目的,需要可溶性化合物,其例如通过合适的取代获得。
另外,混合方法是可行的,其中例如一个或多个层从溶液中施用,并且一个或多个其它层通过气相沉积施用。
这些方法对于本领域的技术人员而言是通常已知的,并且本领域技术人员可在不付出创造性劳动的情况下施用到包含本发明的化合物的有机电致发光器件。
与现有技术相比,本发明的化合物和本发明的有机电致发光器件值得注意地具有以下令人惊奇的优点中的一个或多个:
1.用作磷光发光体的基质材料的本发明的化合物产生长寿命。
2.本发明的化合物产生高效率。当化合物用作磷光发光体的基质材料时尤其如此。
3.本发明的化合物产生低工作电压。当化合物用作磷光发光体的基质材料时尤其如此。
具体实施方式
通过以下实施例更详细地说明本发明,但并非意图限制本发明。本领域技术人员将能够在所公开的整个范围内使用给出的信息来实施本发明,并且在不付出创造性劳动的情况下制备本发明的其它化合物并将其用于电子器件或者采用本发明的方法。
实施例:
合成实施例
除非另有说明,否则下面的合成是在保护气氛下在干燥的溶剂中进行。溶剂和试剂可购自奥德里奇公司(ALDRICH)或ABCR。对于不可商购的反应物给出的数字是相应的CAS号。
a)6-氯-5H-苯并[c][2,1]苯并氮杂磷杂苯
将在70ml三氯化磷中的8g(50mmol)2-氨基联苯在回流下加热8小时,然后在减压下蒸除残留的PCl3,并且将残留物(Ar-NH-PCl2)与0.5g的AlCl3一起加热到180~220℃,持续6小时。将混合物溶解在甲苯中,且通过玻璃棉过滤,因此与盐分离。纯化通过在180~190℃(0.05mm)下升华进行,以白色针形式得到,其对水解非常敏感。产量:4.2g(24mmol);理论值的42%;纯度:97%,NMR。
以下化合物可以类似方式制备:
b)6-苯基-5H-苯并[c][2,1]苯并氮杂磷杂苯
在保护气体下,将4.2g(24mmol)6-氯-5H-苯并[c][2,1]苯并氮杂磷杂苯溶解在120ml无水甲苯中。将所述溶液在15分钟内添加到在100ml***中由16.2g(103mmol)溴苯和1.5g锂合成的苯基锂溶液中,并且在回流下煮沸1小时。冷却之后,将混合物添加到冰水中,并且分离出有机相。在减压下浓缩有机相,并且使产物从甲苯中重结晶。产量:3g(11mmol);理论值的61%;纯度:98%,NMR。
以下化合物可以类似方式制备:
c)5,6-二苯基苯并[c][2,1]苯并氮杂磷杂苯
在氩气下,使在220ml无水DMF中的6.8g(25mmol,1.00当量)6-苯基-5H-苯并[c][2,1]苯并氮杂磷杂苯、21.3ml(128mmol,5.2当量)碘苯和7.20g碳酸钾(52.1mmol,2.10当量)的初始装料惰性化。随后,添加0.62g(2.7mmol,0.11当量)1,3-二(2-吡啶基)丙烷-1,3-二酮和0.52g(2.7mmol,0.11当量)碘化铜(I)并且将混合物在140℃下加热三天。反应结束之后,将混合物在旋转蒸发器上小心地浓缩,并且抽滤出沉淀的固体,且用水和乙醇洗涤。粗产物借助于热提取(甲苯/庚烷1:1)纯化两次,并且使获得的固体从甲苯中重结晶。产量:4.5g(12.8mmol);理论值的52%。
以下化合物可以类似方式制备:
通过升华将化合物19c、20c和22c~24c纯化至纯度为99.9%。
d)5,6-二苯基苯并[c][2,1]苯并氮杂磷杂苯-6-氧化物
在室温下将4.5g(12.8mmol)溶解在40ml乙醇中,并且在30分钟内逐滴添加80ml的H2O2(30%)。在70℃下搅拌1小时之后,将100ml二氯甲烷添加到溶液中,分离各相,浓缩有机相,并且将产物从庚烷/二氯甲烷2:1中结晶。产量:3.9g(10.5mmol);理论值的93%。
使化合物1d~3d、5d、7d、9d和10d从甲苯中重结晶,并且最后分级升华两次(p为约10-6mbar,T=330~450℃)。
e)2-溴-5,6-二苯基苯并[c][1,2]苯并氮杂磷杂苯-6-氧化物
在0℃下在排除光的情况下,向56g(154mmol)5,6-二苯基苯并[c][2,1]苯并氮杂磷杂苯-6-氧化物在氯仿(1000ml)中的溶液中逐份添加N-溴代琥珀酰亚胺(24.7g,139mmol),并且将混合物在所述温度下搅拌2小时。通过添加亚硫酸钠溶液终止反应,并且将混合物在室温下再搅拌30分钟。相分离之后,将有机相用水洗涤,且将水相用二氯甲烷提取。将合并的有机相经硫酸钠干燥并在减压下浓缩。将残留物溶解于甲苯中并通过硅胶过滤。随后,将粗产物从甲苯/庚烷中重结晶。产量:44g(99mmol),理论值的65%,无色固体。
以下化合物可以类似方式制备:
f)5,6-二苯基-2-(9-苯基咔唑-3-基)苯并[c][1,2]苯并氮杂磷杂苯-6-氧化物
将31g(70mmol)2-溴-5,6-二苯基苯并[c][1,2]苯并氮杂磷杂苯-6-氧化物、20.8g(75mmol)苯基咔唑-3-硼酸和14.7g(139mmol)碳酸钠悬浮于200ml甲苯、52ml乙醇和100ml水中。将80mg(0.69mmol)四(三苯基膦)钯(0)添加到所述悬浮液中,并且将反应混合物在回流下加热16小时。冷却之后,去除有机相,通过硅胶过滤,用200ml水洗涤三次,然后浓缩至干。将残留物从庚烷/二氯甲烷中重结晶。产量为33g(55mmol);理论值的79%。
以下化合物可以类似方式获得:
OLED的制造
随后的实施例E1至E9(参见表1)提供本发明的材料在OLED中的用途。
实施例E1~E9的预处理:在涂覆之前用氧等离子体处理用厚度为50nm的结构化ITO(氧化锡铟)涂覆的玻璃板,然后用氩等离子体处理。这些经等离子体处理的玻璃板形成OLED所施用的基底。
OLED基本上具有以下层结构:基底/空穴注入层(HIL)/空穴传输层(HTL)/电子阻挡层(EBL)/发光层(EML)/任选的空穴阻挡层(HBL)/电子传输层(ETL)/任选的电子注入层(EIL),且最后是阴极。阴极由厚度为100nm的铝层形成。OLED的精确结构可在表1中见到。制造OLED所需的材料示于表2中。
所有材料都通过在真空室中热气相沉积施用。在这种情况下,发光层总是由至少一种基质材料(主体材料)和发光掺杂剂(发光体)组成,所述发光掺杂剂通过共蒸发以特定体积比例添加到一种或多种基质材料中。以例如IC1:IC2:TEG1(55%:35%:10%)的形式给出的细节在此意指材料IC1以55%的体积比例、IC2以35%的体积比例且TEG1以10%的体积比例存在于层中。类似地,电子传输层也可由两种材料的混合物组成。
以标准方式表征OLED。电致发光光谱在1000cd/m2的亮度下确定,并由此计算CIE1931x和y色坐标。
本发明的混合物在OLED中的用途
本发明的材料可用作磷光绿色OLED中的发光层中的基质材料。结果整理在表3中。
表1:OLED的结构
表2:用于OLED的材料的结构式
表3:电致发光器件的结果
Claims (14)
1.一种式(1)的化合物,
其中使用的符号如下:
Z在每种情况下相同或不同并且是PAr2或S(=O);
E在每种情况下相同或不同,且当E键合的符号Z是PAr2时,所述E是O或S,并且当E键合的符号Z是S(=O)时,所述E是O;
L选自单键、NAr2、O、S、S(=O)2、P(=O)Ar2、-X=X-和-C(=O)-NAr2-;
X在每种情况下相同或不同并且是CR或N,其中每个环中不超过两个X基团是N;或者两个相邻的X是下式(2)、(3)或(4)的基团:
其中虚线键指示所述基团在所述式(1)中的连接;
Y在每种情况下相同或不同并且是CR或N,其中每个环中不超过两个Y基团是N;
Ar1、Ar2在每种情况下相同或不同并且是芳族或杂芳族环系,所述芳族或杂芳族环系具有5至40个芳族环原子且可被一个或多个R基团取代,其中Ar1和Ar2不彼此连接,条件是与Ar1键合的取代基R不是氟;
A在每种情况下相同或不同并且是NAr2、O、S或CR2;
V在每种情况下相同或不同并且是-NAr2-Z(=E)-;
R在每种情况下相同或不同并且是H,D,F,Cl,Br,I,N(Ar3)2,OAr3,SAr3,CN,NO2,NAr3R1,N(R1)2,OR1,SR1,COOR1,C(=O)N(R1)2,Si(R1)3,B(OR1)2,C(=O)R1,P(=O)(R1)2,S(=O)R1,S(=O)2R1,OSO2R1,具有1至20个碳原子的直链烷基基团或具有2至20个碳原子的烯基或炔基基团或具有3至20个碳原子的支链或环状的烷基基团,其中所述烷基、烯基或炔基基团在每种情况下可被一个或多个R1基团取代,其中一个或多个不相邻的CH2基团可被Si(R1)2、C=O、NR1、O、S或CONR1替换,或具有5至40个芳族环原子并且在每种情况下可被一个或多个R1基团取代的芳族或杂芳族环系;同时,两个R基团也可一起形成脂族或杂脂族环系;
Ar3在每种情况下相同或不同并且是芳族或杂芳族环系,所述芳族或杂芳族环系具有5至30个芳族环原子且可被一个或多个R1基团取代;
R1在每种情况下相同或不同并且是H,D,F,Cl,Br,I,N(R2)2,CN,NO2,OR2,SR2,Si(R2)3,B(OR2)2,C(=O)R2,P(=O)(R2)2,S(=O)R2,OSO2R2,具有1至20个碳原子的直链烷基基团或具有2至20个碳原子的烯基或炔基基团或具有3至20个碳原子的支链或环状的烷基基团,其中所述烷基、烯基或炔基基团在每种情况下可被一个或多个R2基团取代,其中一个或多个不相邻的CH2基团可被Si(R2)2、C=O、NR2、O、S或CONR2替换,或具有5至40个芳族环原子并且在每种情况下可被一个或多个R2基团取代的芳族或杂芳族环系;同时,两个或更多个R1基团可一起形成脂族环系;
R2在每种情况下相同或不同并且是H,D,F,CN,或具有1至20个碳原子的脂族、芳族或杂芳族有机基团,尤其是烃基基团,其中一个或多个氢原子也可被F替换;
其中从本发明中排除以下化合物:
4.根据权利要求1至3中的一项或多项所述的化合物,其特征在于不为所述式(2)、(3)或(4)的基团的符号X在每种情况下相同或不同且是CR,并且其特征在于符号Y在每种情况下相同或不同且是CR。
8.根据权利要求1至7中的一项或多项所述的化合物,其特征在于Z是PAr2,且E是O,并且L是单键。
9.根据权利要求1至8中的一项或多项所述的化合物,其特征在于Ar1和Ar2在每种情况下相同或不同,并且是芳族或杂芳族环系,所述芳族或杂芳族环系具有6至24个芳族环原子且可被一个或多个R基团取代,其中在Ar1的情况下,R基团不是氟。
10.根据权利要求1至9中的一项或多项所述的化合物,其特征在于R在每种情况下相同或不同并且选自H,D,F,N(Ar3)2,CN,OR1,具有1至10个碳原子的直链烷基基团或具有2至10个碳原子的烯基基团或具有3至10个碳原子的支链或环状的烷基基团,其中所述烷基或烯基基团在每种情况下可被一个或多个R1基团取代,其中一个或多个不相邻的CH2基团可被O替换,或具有6至30个芳族环原子且在每种情况下可被一个或多个R1基团取代的芳族或杂芳族环系;同时,两个R基团也可一起形成脂族环系。
11.一种制剂,所述制剂包含至少一种根据权利要求1至10中的一项或多项所述的化合物和至少一种另外的化合物和/或溶剂。
12.根据权利要求1至10中的一项或多项所述的化合物在电子器件中的用途。
13.一种电子器件,所述电子器件包含至少一种根据权利要求1至10中的一项或多项所述的化合物。
14.根据权利要求13所述的电子器件,所述电子器件是有机电致发光器件,其特征在于根据权利要求1至10中的一项或多项所述的化合物存在于发光层中,尤其是作为基质材料存在于发光层中,和/或存在于电子传输层中和/或空穴阻挡层中和/或空穴传输层中和/或激子阻挡层中。
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CN113980055B (zh) * | 2021-11-26 | 2023-09-29 | 南阳师范学院 | 具联芳骨架的环状膦酰胺类衍生物、合成方法及应用 |
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US20220020934A1 (en) | 2022-01-20 |
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