CN101720330A - 发光Cu(I)络合物 - Google Patents
发光Cu(I)络合物 Download PDFInfo
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- CN101720330A CN101720330A CN200880021501A CN200880021501A CN101720330A CN 101720330 A CN101720330 A CN 101720330A CN 200880021501 A CN200880021501 A CN 200880021501A CN 200880021501 A CN200880021501 A CN 200880021501A CN 101720330 A CN101720330 A CN 101720330A
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- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 11
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Images
Classifications
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- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5045—Complexes or chelates of phosphines with metallic compounds or metals
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Abstract
式L Cu A的电中性金属络合物或其质子化或烷基化形式或盐在场致发光用途中表现出良好的发光效率，其中L代表中性配体，尤其是二齿配体，A代表通过至少一个选自N、P、S的杂原子与Cu结合的单阴离子配体，尤其是二齿配体；或其中具有上述特征的配体L和A通过至少一个化学键互连，形成一个共用四齿配体。
Description
本发明涉及Cu(I)金属离子的中性络合物的设计和表征、其特别在发光电子器件、尤其是发射蓝光和绿光的发光电子器件中的应用，以及相应的用途和工艺，以及可用于制备本络合物的一些新型配体。
Rader等人(J.Am.Chem.Soc.103，5906(1981))和Tsuboyama等人(US 2005/014024；WO 03/095587)已经描述了许多场致发光Cu(I)络合物。某些单核电中性铜络合物已主要被提议用作催化剂，参见例如lnoue等人，Macromolecules 36，7432(2003)。
现在已经发现新的一组电中性Cu(I)络合物，其对于发光器件，例如OLED(有机发光二极管)或LEC(发光电池，light emitting cell)，具有尤其有价值的性能，例如在光谱发射特征以及在包括THF、甲苯、二氯甲烷在内的许多溶剂中的良好溶解性方面。含有本发明化合物的器件的其它优点包括易处理、可弃性和低毒性，以及高使用寿命/对氧化剂的低敏感性。
本发明因此涉及式(I)的电中性络合物或其质子化或烷基化形式或盐
L Cu A (I)
其中
L代表中性配体，且
A代表通过至少一个选自N、P、S的杂原子与Cu结合的单阴离子配体；
或其中具有上述特征的配体L和A通过至少一个化学键互连，形成一个共用四齿配体。
A通常是含有键合杂原子(尤其是氮和/或硫)作为环原子的杂环配体。下文进一步列举此类杂环的实例(C1-C18，其任选被取代)。
式I的络合物通常是四配位络合物，例如其中L和A都是二齿配体，L是三齿配体且A是单齿配体，L是单齿配体且A是三齿配体，或具有上述特征的L和A通过至少一个化学键互连形成一个共用四齿配体。
本发明化合物，尤其是其中配体A中的杂原子为氮的那些，进一步可用于传感用途，因为发现，通过尤其在氮原子处的配体改性，例如质子化或烷基化(例如甲基化)，可以实现发射颜色的显著改变。结果，此类络合物不再是电中性的，而是由于改性剂(如H+或CH3+)的加合而带正电荷。由此改性的络合物因此描述为原始电中性络合物的加合盐，例如氢卤化物、硫酸氢盐、甲基硫酸盐或甲基卤化物。
在一类具有主要技术意义的式I的络合物或其质子化或甲基化形式或盐中，
L代表二齿中性配体，且
A代表通过至少一个选自N、P、S的杂原子与Cu结合的二齿单阴离子配体；
或其中具有上述特征的配体L和A通过至少一个化学键互连，形成一个共用四齿配体。
在优选配体A中，负电荷主要位于所提到的杂原子上。通常，该化合物呈现四面体几何。它们尤其耐受双氧和溶剂。
本络合物在充氧溶液中微弱发光，但是在固态或者如果与例如PMMA或PVK之类的聚合物混合则会变成强发光。
如上所述，这2个配体A和L可通过桥基或一个或多个化学键互连形成一个化学体(一个共用四齿配体)。通过用化学键替代各配体上的至少一个H原子，在形式上实现该互连。
优选的一组络合物含有一个基于双膦衍生物的配体和一个带负电荷的N-N配体。
烷基代表任何非环式饱和一价烃基；链烯基是指含有至少一个碳-碳双键的此类基团(例如烯丙基)；类似地，炔基是指含有至少一个碳-碳三键的此类基团(例如炔丙基)。在链烯基或炔基含有多于一个双键的情况下，这些键通常不是累积在一起，而是以交替顺序排列，如在-[CH＝CH-]n或-[CH＝C(CH3)-]n中，其中n可以是例如2-50。优选的烷基含有1-22个碳原子；优选的链烯基和炔基分别含2-22个碳原子，尤其是3-22个碳原子。
具有多于一个、尤其多于2个碳原子的任何烷基残基，或作为另一残基的一部分的此类烷基或亚烷基残基，可以被杂官能团(例如O、S、COO、OCNR10、OCOO、OCONR10、NR10CNR10或NR10)插入，其中R10是H、C1-C12烷基、C4-C12环烷基。它们可以被一个或多个这些间隔基插入，一个基团在各情况下一般插入C-H中，或优选插入碳-碳键中，不出现杂-杂键，例如O-O、S-S、NH-NH等；如果被插入的烷基另外被取代，取代基通常不在杂原子的α位。如果两个或多个-O-、-NR10-、-S-类型的插入基团出现在一个基团中，它们通常是相同的。
因此，术语烷基，无论在何处使用，主要包括特别地未被插入的、和适当时被取代的C1-C22烷基，例如甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、2-乙基丁基、正戊基、异戊基、1-甲基戊基、1，3-二甲基丁基、正己基、1-甲基己基、正庚基、异庚基、1，1，3，3-四甲基丁基、1-甲基庚基、3-甲基庚基、正辛基、2-乙基己基、1，1，3-三甲基己基、1，1，3，3-四甲基戊基、壬基、癸基、十一烷基、1-甲基十一烷基、十二烷基、1，1，3，3，5，5-六甲基己基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基。烷氧基是烷基-O-；烷基硫代是烷基-S-。
术语芳基或芳族残基，无论在何处使用，主要包括C1-C18芳族残基，其可以是含有一个或多个主要选自O、N和S的杂原子作为环结构的一部分的杂环；其优选包含具有可能的最高双键数的单环环或多环环体系，例如优选苯基、萘基、anthrachinyl、蒽基或芴基。烃芳基或芳烃的实例主要是C6-C18，包括苯基、萘基、anthrachinyl、蒽基、芴基；杂环的实例(C1-C18)包括下表中的那些：
以及氮杂萘基、菲酚基(phenanthrolyl)、三嗪基、四氢萘基、噻吩基、吡唑基、咪唑基、
如果存在的话，取代基通常选自卤素、C1-C18烷氧基、C1-C18烷基、C2-C18链烯基、C2-C18炔基、C1-C18烷基硫代、C1-C18酰基、C5-C10芳基、C4-C10杂芳基、C3-C12环烷基、C1-C18酰氧基、C5-C10芳氧基、C3-C12环烷氧基、被一个或多个R′取代的上述烃残基，或选自残基COR、CH＝NR、CH＝N-OH、CH＝N-OR、COOR、CONHR、CONRR′、CONH-NHR、CONH-NRR′、SO2R、SO3R、SO2NHR、SO2NRR″、SO2NH-NHR、SO2NH-NRR′、S(O)R、S(O)OR、S(O)NHR、S(O)NRR′、S(O)NH-NHR、S(O)NH-NRR′、SiRR′R″、PORR′、PO(OR)R′、PO(OR)2、PO(NHR)2、PO(NRR′)2、CN、NO2、NHR、NRR′、NH-NHR、NH-NRR′、CONROH；
其中R、R′和R″独立地选自C1-C12烷基、C1-C12卤烷基、C2-C8链烯基、C2-C8炔基、C5-C10芳基、C2-C18酰基、C3-C12环烷基，例如选自C1-C6烷基、苯基、环戊基、环己基；
且R也可以是氢。
当残基被取代时，取代基通常键合到碳原子上，并优选选自C1-C18烷氧基；C1-C18烷基；被卤素、OH、COOH或CONH2取代的所述烷基或烷氧基；被O、S、COO或CONH插入的所述烷基或烷氧基；C2-C8链烯基；C2-C8炔基；C4-C12环烷氧基；C4-C12环烷基；OH；COOH；卤素；C1-C14芳基，例如苯基或萘基；被C1-C8烷基、C1-C8烷氧基、C1-C8卤烷基、C2-C8链烯基、C2-C8炔基、C1-C8烷氧基羰基、C1-C8烷酰氧基、硝基、卤素、OH、COOH、CONH2取代的所述芳基；其中饱和碳也可以被氧代(＝O)取代，相邻取代基可连接到一起以例如形成碳环、内酯、酸酐、环醚(例如氧杂环丁烷(oxethane)或氧杂环丙烷(epoxy))、或酰亚胺环。优选的取代基是卤素、芳基、烷基、链烯基、烷氧基。
卤素是指I、Br、Cl、F，优选为Cl、F，尤其是F。卤烷基是指被卤素取代的烷基；这包括全卤代烷基，例如全氟烷基，尤其是C1-C4全氟烷基，其是支链或直链基团，例如-CF3、-CF2CF3、-CF2CF2CF3、-CF(CF3)2、-(CF2)3CF3和-C(CF3)3。
术语链烯基，无论在何处使用，主要包括直链或支链的、特别是未被插入的，以及适当时被取代的C2-C22烷基，例如乙烯基、烯丙基等。
炔基，如C2-24炔基，是直链或支链的，并优选为C2-8炔基，其可以是未取代的或取代的，例如乙炔基、1-丙炔-3-基、1-丁炔-4-基、1-戊炔-5-基、2-甲基-3-丁炔-2-基、1，4-戊二炔-3-基、1，3-戊二炔-5-基、1-己炔-6-基、顺式-3-甲基-2-戊烯-4-炔-1-基、反式-3-甲基-2-戊烯-4-炔-1-基、1，3-己二炔-5-基、1-辛炔-8-基、1-壬炔-9-基、1-癸炔-10-基或1-二十四炔-24-基。
脂族环状残基包括环烷基、脂族杂环残基及其不饱和变体，例如环烯基。环烷基，例如C3-C18环烷基，优选为C3-C12环烷基或被1至3个C1-C4烷基取代的所述环烷基，并包括环丙基、环丁基、环戊基、甲基环戊基、二甲基环戊基、环己基、甲基环己基、二甲基环己基、三甲基环己基、叔丁基环己基、环庚基、环辛基、环壬基、环癸基、环十二烷基、1-金刚烷基或2-金刚烷基。环己基、1-金刚烷基和环戊基是最优选的。C3-C12环烷基包括环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环壬基、环癸基、环十一烷基、环十二烷基；这些残基中优选的是C3-C6环烷基以及环十二烷基，尤其是环己基。存在的其它环结构是通常含有5至7个环元的杂环脂族环，这些环元中至少1个、尤其1至3个是通常选自O、S、NR10的杂残基，其中R10如上文中对插入的NR10-基团解释的那样；实例包括被S、O或NR10插入的C4-C18环烷基，如哌啶基、四氢呋喃基、哌嗪基和吗啉基。可以由这些结构通过夺取2个相邻环元上的氢原子并在它们之间形成双键来生成不饱和变体；此类残基的一个实例是环己烯基。
烷氧基，例如C1-C24烷氧基，是直链或支链基团，例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基、戊氧基、异戊氧基或叔戊氧基、庚氧基、辛氧基、异辛氧基、壬氧基、癸氧基、十一烷氧基、十二烷氧基、十四烷氧基、十五烷氧基、十六烷氧基、十七烷氧基和十八烷氧基。
环烷氧基是例如环戊氧基、环己氧基、环庚氧基或环辛氧基，或被1至3个C1-C4烷基取代的所述环烷氧基，例如甲基环戊氧基、二甲基环戊氧基、甲基环己氧基、二甲基环己氧基、三甲基环己氧基或叔丁基环己氧基。
酰基代表磺酸或特别是有机羧酸的残基，其在形式上通过夺取酸OH而形成；实例是甲酰基、乙酰基、丙酰基、苯甲酰基。通常，C1-C18酰基代表基团X′-R11，其中X′是CO或SO2，且R11选自一价脂族或芳族有机残基，通常具有最高300的分子量；例如，R11可以选自C1-C18烷基、C2-C18链烯基、可以是未取代的或被C1-C8烷基或卤素或C1-C8烷氧基取代的C5-C10芳基、可以是未取代的或在芳族部分中被C1-C8烷基或卤素或C1-C8烷氧基取代的C6-C15芳基烷基、C4-C12环烷基，并且在X′是CO的情况下，R11也可以是H。酰基优选是有机酸-CO-R11的脂族或芳族残基，通常具有1至30个碳原子，其中R11包括芳基、烷基、链烯基、炔基、环烷基，它们各自可以是取代的或未取代的和/或如其它地方所述(尤其如对烷基残基所述)被插入，或R′可以是H(即，COR′是甲酰基)。因此，优选如对芳基、烷基等所述那样；更优选的酰基残基是取代或未取代的苯甲酰基，取代或未取代的C1-C17烷酰基或烯酰基，例如乙酰基或丙酰基或丁酰基或戊酰基或己酰基、取代或未取代的C5-C12环烷基羰基，例如环己基羰基。
配体L通常符合式II：
D1-G-D2 (II)
其中G代表二价有机桥连基或直接键，且
D1和D2各自独立地代表含有选自氮、硫和/或磷的给电子杂原子的有机残基。
配体A通常符合式III：
D3-G’-D4 (III)
其中G′代表有机桥连基或直接键，
D3代表含有选自氮、氧、硫、磷的给电子杂原子的有机残基，且
D4代表含有选自氮、硫的阴离子杂原子的有机残基；
对于某些配体A，其可以用式IV表示：
其中
Z是与氮原子一起形成不饱和或芳族4元至8元环的有机桥连基，其任选地可以被取代，且
Y-是通过阴离子氮与中心Cu原子结合的脂族或芳族、环状或非环状的有机残基。
在优选的式III配体中，G′代表直接键；
D3代表具有5至14个环原子的不饱和或芳族杂环残基，例如叔芳族氨基残基或相应的氧杂或硫杂残基；
D4代表具有5至14个环原子的不饱和或芳族N-杂环残基的阴离子；
或者配体D3-G’-D4代表符合式V的由具有8至14个环原子的至少2个稠合的环(annealed rings)构成的体系：
其任选地可以被取代，其中Z′是含有至少一个选自氮、氧、硫、磷的给电子杂原子、并和与其键合的碳原子一起形成不饱和或芳族4元至8元环的有机桥连基，其任选地可以被取代；且其中Z和Z″独立地选自与氮原子一起构成不饱和或芳族4元至8元环的有机桥连基和直接键，其任选地可以被取代，并且其中Z和Z″中的至少一个不是直接键。
D3通常选自吡啶基、嘧啶基、哒嗪基、吡唑基、吡喃基、香豆素基(cumaryl)、蝶啶基、苯硫基、苯并苯硫基、呋喃基、苯并呋喃基、噻唑基、噻吩并噻吩基、二硫代吲丹烯基(dithiaindacenyl)、喹啉基(chinolyl)、异喹啉基(isochinolyl)、喹喔啉基(chinoxalyl)、吖啶基、氮杂萘基、菲酚基(phenanthrolyl)、三嗪基、噻吩基、
它们各自是未取代的或取代的；
D4来自在残基嘌呤基、吡咯基、吲哚基、咔唑基、三唑基、苯并三唑基、吡唑基、苯并吡唑基、咪唑基、苯并咪唑基、四唑基的N-脱质子化之后可获得的阴离子残基，它们各自是未取代的或取代的；
或者配体D3-G’-D4具有式V，其中Z′是与2个连接碳原子键合的有机桥连基，并选自NCHCHCH、CHNCHCH、NNCHCH、NCHNCH、NCHCHN、NNNCH、NNCHN、OCHCH、CHOCH、OCHN、SCHCH、SCHN、CHSCH，它们的碳原子可任选被取代；且Z″-N--Z是与2个连接碳原子键合的有机桥连基，并且选自N-CHCH、CHN-CH、N-CHN、N-NCH、N-NN，它们的碳原子(如果存在的话)可任选被取代；
特别地，其中来自D3或Z′的杂原子以及阴离子氮在1，3位或1，4位或1，5位。
式II的优选配体L是下述那些：
其中G代表选自C1-C8亚烷基、C2-C8亚烯基、C2-C8亚炔基、O、S、SO、SO2、O插入的C2-C6亚烷基、亚苯基、取代的亚苯基的二价有机桥连基，或代表直接键；且
D1和D2各自独立地选自式VI的氧膦基残基和D3，
P(D5)(D6)D7- (VI)
其中D3是具有5至14个环原子的不饱和或芳族N-杂环残基，例如叔芳族氨基残基；D3优选选自吡啶基、嘧啶基、哒嗪基、吡唑基、吡喃基、香豆素基(cumaryl)、蝶啶基、苯硫基、苯并苯硫基、呋喃基、苯并呋喃基、噻唑基、噻吩并噻吩基、二硫代吲丹烯基(dithiaindacenyl)、喹啉基(chinolyl)、异喹啉基(isochinolyl)、喹喔啉基(chinoxalyl)、吖啶基、氮杂萘基、菲酚基(phenanthrolyl)、三嗪基、噻吩基、
它们各自是未取代的或取代的；
D5和D6独立地是C1-C8烷基、C2-C8链烯基、C2-C8链炔基、或优选C4-C10芳基，例如苯基，它们各自是未取代的或取代的；且
D7是C1-C8亚烷基、C2-C8亚烯基、C2-C8亚炔基、或优选C4-C10亚芳基，例如亚苯基，它们各自是未取代的或取代的；
特别地，其中给电子杂原子在1，4位、1，5位、1，6位、1，7位、1，8位或1，9位。
本发明的大量配体是新型化合物。本发明因此进一步涉及下式的3-吡啶基取代的1，2，4-三唑的用途，用作用于制备过渡金属络合物(例如Cu、Fe、Ni、Ir、Rh、Ru、Pt、Pd络合物)的配体；
以及涉及下式的化合物：
其中
i和m独立地为0、1或2；
k为3至5；
R独立地为C1-C12烷基、C2-C8链烯基、卤素、硝基、氨基、甲氧基；
X是H、C1-C12烷基，或阳离子同等物，例如Li+、Na+、K+、1/2Ca2+、1/2Mg2+、1/2Zn2+。
上式仅显示了本配体A(或其质子化形式)的可能的共振/互变形式之一，其它形式也是可行的，并包含在本发明保护范围内。
本发明的络合物和配体可以方便地与本领域的已知方法(例如一开始提到的)类似地获得。例如，本发明的Cu(I)络合物的制备可以始于合适的铜盐或铜络合物，例如CuHal(其中Hal代表卤素阴离子，例如氯阴离子或溴阴离子)、CuPF6(优选是与例如乙腈等中性配体的络合物的形式)，其然后与配体L和配体A反应，后者优选为其质子化(＝中性)形式。通常使用有机溶剂或溶剂混合物、优选在避开氧的情况下进行该反应。后处理遵循标准程序，例如过滤、干燥等。
配体L是本领域公知的，许多是市售的。
配体A的一些质子化前体也是本领域已知的，另一些可以与已知化合物(例如US 2006/286404中描述的那些)类似地获得。
本发明还涉及包含该金属络合物的电子器件及其制造方法。该电子器件可以包含位于两个电接触层之间的至少一种有机活性材料，其中该器件的至少一个层包括所述金属络合物。该电子器件可以包含阳极层(a)、阴极层(e)和活性层(c)。与阳极层(a)相邻的是任选的空穴注入/传输层(b)，与阴极层(e)相邻的是任选的电子注入/传输层(d)。层(b)和(d)是电荷传输层的实例。
活性层(c)可以包含至少大约1重量％的本发明的金属络合物。
在一些实施方案中，活性层(c)可以是基本100％的该金属络合物，因为不需要基质电荷传输材料，例如Alq3。“基本100％”是指该金属络合物是该层中仅有的材料，可能的例外是来自形成层的过程的杂质或偶发副产物外。尽管如此，在一些实施方案中，该金属络合物可以是基质材料内的掺杂剂，其通常用于辅助活性层(c)内的电荷传输。活性层(c)，包括任何金属络合物，可以是小分子活性材料或聚合活性材料。
所述器件可以包括与阳极层(a)或阴极层(e)相邻的载体或基底(未显示)。最常见地，该载体与阳极层(a)相邻。该载体可以是挠性或刚性的，有机或无机的。通常，使用玻璃或挠性有机薄膜作为载体。阳极层(a)是与阴极层(e)相比更有效注入空穴的电极。阳极可以包括含有金属、混合金属、合金、金属氧化物或混合金属氧化物的材料。阳极层(a)内的合适的金属元素可以包括第4、5、6和8至11族过渡金属。如果阳极层(a)是要透光的，则可以使用第12、13和14族金属的混合金属氧化物，如氧化锡铟。阳极层(a)的材料的一些非限制性具体实例包括氧化锡铟(“ITO”)、氧化锡铝、金、银、铜、镍和硒。
阳极层(a)可以通过化学或物理气相沉积法或旋转浇注(spin-cast)法形成。化学气相沉积可以以等离子体增强的化学气相沉积(“PECVD”)或金属有机化学气相沉积(“MOCVD”)的形式进行。
物理气相沉积可以包括所有形式的溅射(例如离子束溅射)、电子束蒸发和电阻蒸发。
物理气相沉积的具体形式包括例如磁控管溅射或电感耦合等离子体物理气相沉积(“ICP-PVD”)。这些沉积技术是半导体制造领域内公知的。
空穴传输层(b)可以与阳极相邻。空穴传输小分子化合物和聚合物都可使用。
常用的空穴传输分子包括：N，N′-二苯基-N，N′-双(3-甲基苯基)-[1，1′-联苯基]-4，4′-二胺(TPD)、1，1-双[(二-4-甲苯基氨基)苯基]环己烷(TAPC)、N，N′-双(4-甲基苯基)-N，N′-双(4-乙基苯基)-[1，1′-(3，3′-二甲基)联苯基]4，4′-二胺(ETPD)、四-(3-甲基苯基)-N，N，N′，N′-2，5-亚苯基二胺(PDA)、a-苯基-4-N，N-二苯基氨基苯乙烯(TPS)、对-(二乙基氨基)苯甲醛二苯基腙(DEH)、三苯胺(TPA)、双[4-(N，N-二乙基氨基)-2-甲基苯基](4-甲基苯基)甲烷(MPMP)、1-苯基-3-[对-(二乙基氨基)苯乙烯基]-5-[对-(二乙基氨基)苯基]吡唑啉(PPR或DEASP)、1，2-反式-双(9H-咔唑-9-基)环丁烷(DCZB)、N，N，N′，N′-四(4-甲基苯基)-(1，1′-联苯基)-4，4′-二胺(TTB)、4，4’-N，N-二咔唑-联苯基(CBP)、N，N-二咔唑基-1，4-二亚甲基-苯(DCB)、卟啉化合物(porphyrinic compounds)及其组合。
常用的空穴传输聚合物是聚乙烯基咔唑、(苯基甲基)聚硅烷、聚(3，4-亚乙二氧基噻吩)(PEDOT)和聚苯胺。可以通过将空穴传输分子(例如上文提到的那些)掺杂到聚合物(例如聚苯乙烯和聚碳酸酯)中来获得空穴传输聚合物。
可以使用任何传统方法，包括旋涂、浇注和印刷，例如凹版印刷，形成空穴注入/传输层(b)。该层也可以通过喷墨印刷、热图案化或化学或物理气相沉积法施用。
通常，在相同的平版印刷操作过程中将阳极层(a)和空穴注入/传输层(b)图案化。图案可以按需要变化。可以通过例如在施用第一电接触层材料之前将图案化掩模或抗蚀剂放置在第一挠性复合阻隔结构上而按图案形成层。或者，这些层可以整层施用(也称作覆盖沉积)，然后使用例如图案化的抗蚀层和湿化学或干蚀刻技术将其图案化。也可以使用本领域公知的其它图案化方法。在该电子器件位于阵列中时，阳极层(a)和空穴注入/传输层(b)通常形成为具有以基本相同方向延伸的长度的基本平行的条带。
活性层(c)可以包含本文所述的金属络合物。所选特定材料取决于具体用途、操作过程中所用的电势或其它因素。活性层(c)可以包含能够传输电子和/或空穴的基质材料，其被可以捕集电子、空穴和/或激子的发射材料掺杂，以使得经由光电发射机制从该发射材料中释放激子。活性层(c)可以包含兼具传输和发射性质的单一材料。无论发射材料是掺杂剂还是主要成分，该活性层都可以包含其它材料，例如调节该发射材料的发射的掺杂剂。活性层(c)可以包括多种发射材料，它们能够联合发射所需光谱的光。磷光发射材料的实例包括本发明的金属络合物。荧光发射材料的实例包括DCM和DMQA。基质材料的实例包括Alq3、CBP和mCP。在全文经此引用并入本文的US-B-6,303,238中公开了发射材料和基质材料的实例。
活性层(c)可以由溶液通过任何传统技术施用，包括旋涂、浇注和印刷。该活性有机材料可以根据材料性质通过气相沉积法直接施用。
任选的层(d)既可用于促进电子注入/传输，又充当缓冲层或封闭层以防止层界面处的猝灭反应。更具体地，层(d)可以促进电子迁移率和降低猝灭反应的可能性，否则，如果层(c)和(e)直接接触，则存在这种可能性。任选的层(d)的材料的实例包括金属-螯合的喔星化物(oxinoid)，例如，三(8-羟基喹啉合)铝(Alq3)等；基于菲咯啉的化合物，例如2，9-二甲基-4，7-二苯基-1，10-菲咯啉(“DDPA”)、4，7-二苯基-1，10-菲咯啉(“DPA”)等；唑化合物，例如2-(4-联苯基)-5-(4-叔丁基苯基)-1，3，4-噁二唑(“PBD”)等、3-(4-联苯基)-4-苯基-5-(4-叔丁基苯基)-1，2，4-三唑(“TAZ”)等；其它类似化合物；或其任何一种或多种组合。或者，任选的层(d)可以是无机的，并包含BaO、LiF、Li2O等。
电子注入/传输层(d)可以使用任何传统方式形成，包括旋涂、浇注和印刷，例如凹版印刷。该层也可以通过喷墨印刷、热图案化、或化学或物理气相沉积法施用。
阴极层(e)是特别有效地注入电子或负电荷载流子的电极。阴极层(e)可以是功函低于第一电接触层(在这种情况下为阳极层(a))的任何金属或非金属。第二电接触层所用的材料可以选自第1族碱金属(例如Li、Na、K、Rb、Cs)、第2族(碱土)金属、第12族金属、稀土、镧系元素(例如Ce、Sm、Eu等)和锕系元素。也可以使用如铝、铟、钙、钡、钇和镁及其组合的材料。也可以在有机层和阴极层之间沉积含Li的有机金属化合物、LiF和Li2O以降低工作电压。阴极层(e)所用材料的具体非限制性实例包括钡、锂、铈、铯、铕、铷、钇、镁或钐。
阴极层(e)通常通过化学或物理气相沉积法形成。通常，如上文关于阳极层(a)和任选的空穴注入层(b)所述，将阴极层图案化。如果所述器件位于阵列中，可以将阴极层(e)图案化成基本平行的条带，其中阴极层条带的长度以基本相同方向延伸并基本垂直于阳极层条带的长度。
在交点(在从平视或顶视观察阵列时，阳极层条带与阴极层条带在此处交叉)处形成被称作像素的电子元件。
在另一些实施方案中，可以在有机电子器件内存在附加层(s)。例如，空穴注入层(b)和活性层(c)之间的层(未显示)可能促进正电荷传输、层的带隙匹配，充当保护层等。类似地，电子注入层(d)和阴极层(e)之间的附加层(未显示)可能促进负电荷传输、层之间的带隙匹配，充当保护层等。可以使用本领域中已知的层。一些或所有层可以被表面处理以提高电荷载流子传输效率。可以通过权衡提供具有高器件效率的器件的目标以及制造成本、制造复杂性或潜在的其它因素来决定各组成层的材料的选择。
电荷传输层(b)和(d)通常具有与活性层(c)相同的类型。更具体地，如果活性层(c)具有小分子化合物，则电荷传输层(b)和(d)(如果存在任一或二者)可以具有不同的小分子化合物。如果活性层(c)具有聚合物，则电荷传输层(b)和(d)(如果存在任一或二者)也可以具有不同的聚合物。此外，活性层(c)可以是小分子化合物，而其任一相邻电荷传输层可以是聚合物。
各功能层可以由多于一个的层构成。例如，阴极层可以包含第I族金属层和铝层。第I族金属可靠近活性层(c)，且铝可有助于保护该第I族金属远离环境污染物，例如水。
不同层可以具有下述厚度范围(但这不是为了限制)：无机阳极层(a)，通常不大于大约500纳米，例如大约50-200纳米；任选的空穴注入层(b)，通常不大于大约100纳米，例如大约50-200纳米；活性层(c)，通常不大于大约100纳米，例如大约10-80纳米；任选的电子注入层(d)，通常不大于大约100纳米，例如大约10-80纳米；和阴极层(e)，通常不大于大约1000纳米，例如大约30-500纳米。如果阳极层(a)或阴极层(e)需要透过至少一些光，这类层的厚度可能不超过大约100纳米。
所述器件中电子-空穴重组区的位置和因此该器件的发射光谱可能受各层相对厚度的影响。例如，当在电子传输层(d)中使用潜在发光化合物(例如Alq3)时，电子-空穴重组区可位于该Alq3层内。
该发射因而是Alq3的发射，而非所需的窄峰发射。因此，应选择电子传输层的厚度，以使得电子-空穴重组区位于发光层(即活性层(c))内。层厚度的所需比率取决于所用材料的确切性质。
可通过优化所述器件中的其它层来进一步提高用金属络合物制成的器件的效率。例如，可以使用更有效的阴极，例如Ca、Ba、Mg/Ag或LiF/Al。也可采用造成工作电压降低或提高量子效率的成型基底和空穴传输材料。
也可以加入附加层，以调节各种层的能量级和促进场致发光。
根据该电子器件的用途，活性层(c)可以是被信号激活的发光层(例如在发光二极管中)，或是响应辐射能并在有或没有外加电势的情况下(例如检测器或伏打电池)产生信号的材料层。可响应辐射能的电子器件的实例选自光电导管、光敏电阻、光控继电器、光电晶体管和光电管，以及光电池。在阅读本说明书后，技术人员能够选择用于他们具体用途的材料。
所述场致发光器件可用于例如移动电话、电视和个人电脑屏幕中的全色显示板。相应地，本发明还涉及含有本发明的有机发光二极管的器件，其选自固定和移动显示器，例如用于电脑、移动电话、手提电脑、pdas、电视机的显示器、在印刷机、厨房设备、广告板、照明设备、火车和公交车上的信息板和指路牌中的显示器。
在OLEDs中，分别从阴极(e)和阳极(a)层注入光活性层(c)的电子和空穴在活性层(c)中形成带负电荷和带正电荷的极化子。这些极化子在外加电场的影响下迁移，与带相反电荷的物质形成极化子激子，并然后发生辐射重组。可以对该器件施加在阳极和阴极之间的充足电势差，通常小于大约20伏特，且在一些情况下不大于大约5伏特。实际电势差可能取决于该器件在更大电子部件中的应用。在许多实施方案中，在该电子器件的工作过程中，对阳极层(a)施加正电压偏压，阴极层(e)处于基本地电位或0伏特。电池或其它电源可以作为电路的一部分电连接到该电子器件上。
在另一些实施方案中，该金属络合物可用作层(b)或(d)中的电荷传输材料。
当用在层(b)、(c)或(d)中时，该化合物不需要在固体基质稀释剂(例如基质电荷传输材料)中才能生效。基于层的总重量，可以使用具有大于大约1重量％的该金属络合物和最多基本100％该络合物的层作为活性层(c)。在活性层(c)中可以与该络合物一起存在其它材料。例如，可存在荧光染料以改变发光颜色。
也可以添加稀释剂。该稀释剂可以是聚合材料，例如聚(N-乙烯基咔唑)和聚硅烷。其也可以是小分子，例如4，4′-N，N′-二咔唑联苯基或叔芳胺。当使用稀释剂时，该络合物通常以少量存在，基于层的总重量，通常为少于20重量％，优选少于10重量％。
所述金属络合物可用在电子器件之外的其它用途中。例如，该络合物可用作催化剂或指示剂，例如氧敏指示剂、生物鉴定中的磷光指示剂等。
下列实施例仅用于举例说明，无论如何不应被认为以任何方式限制本发明。室温(r.t.)是指20至25℃；“过夜”是指12至16小时的时长。
除非另行指明，百分比按重量计。
实施例或其它地方所用的缩写：
| DMF | 二甲基甲酰胺 |
| THF | 四氢呋喃 |
| DCM | 二氯甲烷 |
| DMF | 二甲基甲酰胺 |
| MS | 质谱法 |
| HRMS | 高分辨质谱法 |
| ESI | 电雾化电离 |
| GC | 气相色谱法 |
| NMR | 核磁共振 |
| PMMA | 聚甲基丙烯酸甲酯 |
| PVK | 聚乙烯基咔唑 |
实验部分
配体合成
合成和表征
所有试剂都是分析级的，并原样使用。根据标准程序提纯溶剂。除非注明，所有反应都在惰性气氛下进行(希莱克技术)。所有柱色谱法(CC)采用普通快速程序用硅胶60(粒度63-200微米，230-400目，Merck)进行。
(吡啶-2-基)氨基腙(1)-在温和加热下使10.4克(0.10摩尔)2-氰基吡啶熔融之后，加入5.3毫升(5.5克，0.11摩尔)一水合肼，生成混浊混合物。加入乙醇(～5毫升)直到混合物变澄清，在室温下将所得溶液搅拌过夜，导致形成凝胶状产物。减压除去所有溶剂，将固体悬浮在石油醚(50毫升)中，在冰浴中冷却并过滤，用冷石油醚洗涤，产生9.9克(73％)氨基腙。该固体可以在没有进一步提纯的情况下使用，或从甲苯中结晶。Mp：94-96℃(文献值95-96℃)。1H NMR(CDCl3，300MHz)：δ8.50(d，J＝4.1Hz，1H，Ar)，8.00(d，J＝8.0Hz，1H，Ar)，7.67(t，J＝6.2Hz，1H，Ar)，7.24(d，J＝6.2Hz)，5.39(s，1H，NH2)，4.60(s，1H，NH2)。
文献：F.H.Case，Journal of Organic Chemistry 1965，30，931。
吡啶-2-基-1，2，4-三唑(2a-2f)-一般程序-向经过火焰干燥、氮气吹扫过的30毫升Schlenk管中加入(吡啶-2-基)氨基腙(2.0克，15毫摩尔)和碳酸钠(1.6克，15毫摩尔)。将烧瓶抽空，并温和加热。冷却后，用氮气吹扫该烧瓶。接着，加入15毫升干燥的二甲基乙酰胺(DMAA)和5毫升干燥的THF，产生浅黄色悬浮液，将其冷却至0℃。在另一个干燥的10毫升Schlenk烧瓶中，将15毫摩尔适当的酰氯溶解在5毫升DMAA中。然后将该溶液逐滴添加到预先冷却的氨基腙混合物中，导致其转变成嫩黄色。将该混合物缓慢升温至室温，并再搅拌5小时，产生稠的黄色混合物。将内容物过滤，用水和EtOH洗涤固体，并使所得浅黄色固体风干。将该固体悬浮在20毫升乙二醇中，并加热至190℃达30分钟，产生浅黄色溶液。冷却至室温后，形成白色固体，将其收集在玻璃料上，用去离子水洗涤。该固体在真空下干燥，且不经进一步提纯即使用。
2-(5-苯基-2H-1，2，4-三唑-3-基)-吡啶(2a)-苯甲酰氯。收率：63％。Mp：212-214℃(文献值：212℃)。1H NMR(300MHz，DMSO)：δ8.73(d，1H，J＝4.3Hz)，8.18(d，1H，J＝7.8Hz)，8.10(d，1H，J＝7.0Hz)，8.02(t，1H，J＝7.6Hz)，7.60-7.40(m，4H)。
文献：R.Hage，R.Prins，J.G.Haasnoot，J.Reedijk，J.G.Vos，Journalof the Chemical Society-Dalton Transactions 1987，1389。
4-(5-吡啶-2-基-1H-1，2，4-三唑-3-基)-苯甲酸(2b)-4-(氯羰基)苯甲酸。收率：55％。1H NMR(300MHz，DMSO)：δ8.77(d，1H，J＝4.8Hz)；8.32(d，1H，J＝7.8Hz)；8.27-8.16(m，3H)；8.08(d，1H，J＝8.3Hz)；7.70(dd，1H，J＝5.3Hz，J＝7.3Hz)；5.45(s，1H)。
2-[5-(2，6-二氟苯基)-2H！-1，2，4-三唑-3-基]-吡啶(2c)-2，6-二氟苯甲酰氯。灰白色粉末。收率：45％。Mp：181-183℃。1H NMR(300MHz，DMSO)：δ9.18(s，1H)，8.74(d，1H，J＝4.3Hz)，8.12(d，1H，J＝7.8Hz)，8.01(t，1H，J＝7.6Hz)，7.60(m，2H)，7.28(t，2H，J＝8.1Hz)。
2-[5-(4-氟-苯基)-2H-1，2，4-三唑-3-基]-吡啶(2d)-4-二氟苯甲酰氯。灰白色粉末。收率：72％。Mp：241-243℃。1H NMR(300MHz，DMSO)：δ14.90(s，1H)，8.73(d，1H，J＝4.33Hz)，8.21-8.07(m，3H)，8.02(dt，1H，J＝7.84Hz)，7.55(dd，1H，J＝6.66Hz)，7.35(t，2H，J＝8.84Hz)。
2-[5-(3，5-二氟苯基)-2H-1，2，4-三唑-3-基]-吡啶(2e)-3，5-二氟苯甲酰氯。灰白色粉末。收率：68％。Mp：254-257℃。1H NMR(300MHz，DMSO)：δ15.09(s，1H)，7.68-7.59(m，1H)，8.18(d，1H，J＝7.8Hz)，8.04(dt，1H，J＝1.1Hz，J＝7.7Hz)，7.75-7.52(m，3H)，7.36(t，1H，J＝9.3Hz)。
2-[5-(2，3，4，5，6-五氟苯基)-2H-1，2，4-三唑-3-基]-吡啶(2f)-五氟苯甲酰氯。棕黄色固体。收率：60％。该产品可以在没有进一步提纯的情况下使用，或通过升华(120℃，油泵)产生白色固体以获得分析级纯度。Mp：＞195℃(dec)。1H NMR(300MHz，DMSO)：δ8.75(d，1H，J＝4.4Hz)，8.11(d，1H，J＝7.8Hz)，8.03(dt，1H，J＝1.5Hz，J＝7.8Hz)，7.57(dd，1H，J＝5.2Hz，J＝6.3Hz)。
[Cu(PP)(NN)]型络合物的合成
(1)Cu(DPEphos)(Phptp)。(NN＝2-(5-苯基-2H-1，2，4-三唑-3-基)-吡啶)
典型程序如下。将[Cu(CH3CN)4]PF6(141毫克，0.26毫摩尔)和双[2-(二苯基膦基)苯基]醚(DPEphos；114.5毫克，0.26毫摩尔)在20毫升干燥THF中的混合物在室温下在N2下搅拌1小时，然后用3-苯基-吡啶-2-基-1，2，4-三唑(Phptp；58.2毫克，0.26毫摩尔)在10毫升THF中的溶液处理。再将该反应混合物搅拌4小时并过滤，将澄清的绿色滤液抽真空。残留物通过使用乙酸乙酯/甲醇＝20∶1的硅色谱法提纯，获得白色产品，产量150毫克(70％)。MS(ESI+，MeOH)：m/z 823.1([M+H]+，30)。元素分析：C：61.31H：4.07N：5.19(实测值)；C：61.67H：4.16N：5.64(计算值)。
合成其它中性Cu(I)络合物的程序与(1)中所述基本相同。仅给出所用配体的量、产品产量和MS。
(2)Cu(DPEphos)(COOHPhptp)。(NN＝4-(5-吡啶-2-基-1H-1，2，4-三唑-3-基)-苯甲酸)(80.3毫克，0.30毫摩尔)。产量：210毫克，(81％)。C50H37CuN4O3P2的HRMS计算值867.3473([M+H]+)；实测值867.1710。
在加入无机酸(例如，HCI、H2SO4；参见图8)后，获得该化合物的质子化形式。
(3)Cu(DPEphos)(2FPhptp)。(NN＝2-[5-(2，6-二氟-苯基)-2H-1，2，4-三唑-3-基]-吡啶)(56.4毫克，0.22毫摩尔)。产量：135毫克，(71％)。MS(ESI+，MeOH)：m/z 859.3([M+H]+，30)。C49H35CuF2N4OP2的HRMS计算值859.3187([M+H]+)；实测值859.1823
(4)Cu(DPEphos)(FPhptp)。(NN＝2-[5-(4-氟-苯基)-2H-1，2，4-三唑-3-基]-吡啶)(257.2毫克，1.0毫摩尔)。产量：630毫克，(75％)。MS(ESI+，MeCN/CHCl3)：m/z 841.4([M+H]+，25)。元素分析：C：69.52H：4.57N：6.49(实测值)；C：69.95H：4.31N：6.66(计算值)。
(5)Cu(DPEphos)(3，5-2FPhptp)。(NN＝2-[5-(3，5-二氟-苯基)-2H-1，2，4-三唑-3-基]-吡啶，256.6毫克，0.94毫摩尔)。产量：570毫克(72％)。MS(ESI+，MeOH)：m/z 859.3([M+H]+，30)。
(6)Cu(DPEphos)(5FPhptp)。(NN＝2-[5-(2，3，4，5，6-五氟-苯基)-2H-1，2，4-三唑-3-基]-吡啶)(581.6毫克，1.86毫摩尔)。产量：965毫克(57％)。MS(ESI+，MeCN/CHCl3)：m/z 642.3([M+H]+，40)。C49H32CuF5N4OP2的HRMS计算值913.1268([M+H]+)；实测值913.1340。
(7)Cu(DPEphos)(Pta)。(NN＝2-(5-苯基-3H-1，2，3-三唑-4-基)-吡啶)(163.7毫克，1.12毫摩尔)。产量：569毫克(68％)。MS(ESI+，MeOH)：m/z 747.4([M+H]+，30)。
(8)Cu(DPEphos)(Pbi)。(NN＝2-吡啶-2-基-1H-苯并咪唑)(324.6毫克，1.66毫摩尔)。产量：700毫克(53％)。MS(ESI+，MeCN/CHCl3)：m/z 796.4([M+H]+，40)。
(9)Cu(DPEphos)(Pid)。(NN＝2-(1H-咪唑-2-基)-吡啶)(260毫克，1.79毫摩尔)。产量：1200毫克(50％)。MS(ESI+，MeCN/CHCl3)：m/z 746.3([IVH-H]+，100)。C44H34CuN3OP2的HRMS计算值746.2538([M+H]+)；实测值746.1546。
(10)Cu(DPEphos)(Aza)。(NN＝1H-吡咯并[2，3-b]吡啶)(123.6毫克，1.02毫摩尔)。产量：366毫克(51％)。MS(ESI+，MeCN/CHCl3)：m/z 719.4([M+H]+，15)。C43H33CuN2OP2的HRMS计算值719.2284([M+H]+)；实测值719.1437。
(11)Cu(PhBisBI)(Pbi)。(NN＝2-吡啶-2-基-1H-苯并咪唑)
MS(ESI+，MeCN/CHCl3)：m/z 720.3([M+H]+，15)。C44H30CuN7的HRMS计算值719.1859([M]+)；实测值719.1846。
(12)Cu(BDPEphos)(3，5-2FPhptp)。(NN＝2-[5-(3，5-二氟-苯基)-2H-1，2，4-三唑-3-基]-吡啶)。产量：1.25克(46％)。MS(ES+，THF)：m/z 899.05([M+H]+，13)。
(13)Cu(DPEphos)(3，5-2F)Pta)(NN＝2-(5-苯基-3H-1，2，3-三唑-4-基)-吡啶。MS(ES+，THF)：m/z 859.155。
(14)Cu(DPEphos)(4-MeOPhptp)。(NN＝2-[5-(4-甲氧基-苯基)-2H-1，2，4-三唑-3-基]-吡啶。MS(ES+，THF)：m/z 853.1908。
这些化合物可溶于THF、甲苯、DCM。已经通过NMR、MS和X射线进行表征。上述化合物(编号如在上述实施例中那样)的结构式汇编在下表中：
光物理学。在Varian Cary 5000双光束UV-Vis-NIR光谱仪上测量吸收谱并校正基线。在配有450W氙弧灯、双光栅激发和发射光单色器(2.1nm/mm分散；1200槽/mm)以及Hamamatsu R928光电倍增管或TBX-4-X单光子计数检测器的HORIBA Jobin-Yvon IBH FL-322 Fluorolog 3光谱仪上记录稳态发射谱。通过标准校正曲线，针对源强度(灯和光栅)和发射光谱响应(检测器和光栅)校正发射和激发光谱。在Fluorolog 3上使用时间相关单光子计数(TCSPC)选项进行时间分辨测量。使用重复频率为10kHz至1MHz的NanoLEDs(295或402nm；FWHM＜750ps)激发该样品。激发源直接安装在样品室上，与双光栅发射光单色器(2.1nm/mm分散；1200槽/mm)呈90°，并由TBX-4-X单光子计数检测器收集。该检测器收集的光子通过时间-幅度转换器(TAC)与激发脉冲相关联。使用IBHDataStation Hub光子计数模块收集信号，并使用市售DAS6软件(HORIBA Jobin Yvon IBH)进行数据分析。通过使换算的χ平方函数(χ2)最小化和加权残差的目检，评估拟合的优良度。在Department ofChemistry，University of Münster中进行光谱和元素(CHN)分析。在循环注入的Bruker Daltonics(Bremen，Germany)MicroTof上记录电雾化电离(ESI)质谱。通过二乙醚在室温下气相扩散到Cu(I)络合物的四氢呋喃溶液中，获得Cu(I)络合物的无色单晶。
根据文献程序制备[Cu(CH3CN)4]PF6：G.J.Kubas，Inorg.Synth.1979，19，90.
在通过溶解和溶剂蒸发加入聚合物基质中后，实现了本络合物的聚合物基应用。使用这种方法获得在PVK层或用于光谱测试的层中含有本络合物的场致发光器件。
附图简述
图1-7显示了所示化合物的激发光谱。
图8显示了实施例2的化合物在质子化后的发射移动。
图9显示了通过x-射线衍射法测得的化合物2(含硫酸盐的质子化形式)的分子结构。
图10显示了通过x-射线衍射法测得的化合物1的分子结构。
图11显示了通过x-射线衍射法测得的化合物5的分子结构。
图12显示了通过x-射线衍射法测得的化合物13的分子结构。
光谱数据(在DCM或THF中的室温吸收谱，在石英上的纯膜的荧光发射、受激态的寿命)汇编在下表中：
a：Cu(I)络合物在THF溶液中的吸收。
B：Cu(I)络合物在被366nm激发的纯膜中的发射和寿命。
HOMO能级：使用
40系统(Radiometer Analytical)进行循环伏安法(CV)，该系统由PGZ301恒电位仪和
4软件构成。工作电极和对电极分别是Pt盘和Pt线，而使用Ag线作为假参比电极。所有玻璃器具都在使用前干燥。将干燥的电解质六氟磷酸四丁铵(大于99.0％纯度)、被分析物和用作参考的二茂铁(FeCp2)在Schlenk烧瓶中在高温和减压下干燥和脱气，以去除任何水分和氧。结果汇编在下表中。
| 化合物编号 | HOMO(eV) |
| 1 | 5.46 |
| 2 | 5.54 |
| 4 | 5.44 |
| 5 | 5.45 |
| 3 | 5.47 |
| 6 | 5.72 |
| 13 | 5.58 |
在固态中的量子产额(QY)：
使用来自Hamamatsu C9920的适当装置，在366nm下激发粉末的情况下，测量粉末的量子产额。结果汇编在下表中。
| 化合物编号 | 激发波长 | QY |
| 1 | 366 | 0.17 |
| 4 | 366 | 0.24 |
| 3 | 366 | 0.23 |
| 5 | 366 | 0.54 |
| 6 | 360 | 0.24 |
| 10 | 340 | 0.14 |
| 2 | 350 | 0.26 |
| 化合物编号 | 激发波长 | QY |
| 12 | 402 | 0.21 |
| 13 | 366 | 0.39 |
通过标准x-射线衍射程序使用单晶测定该络合物的晶体结构。
Claims (15)
1.式I的电中性络合物或其质子化或烷基化的形式或盐：
LCuA (I)
其中
L代表中性配体，且
A代表通过至少一个选自N、P、S的杂原子与Cu结合的单阴离子配体；
或者其中具有上述特征的配体L和A通过至少一个化学键互连，形成一个共用四齿配体。
2.权利要求1的络合物，其是四配位的，且其中配体A是含有键合的杂原子、尤其是氮和/或硫作为环原子的杂环配体。
3.权利要求1的络合物，或其质子化或烷基化的形式或盐，其中：
L代表二齿中性配体，且
A代表通过至少一个选自N、P、S的杂原子与Cu结合的二齿单阴离子配体；
或者其中具有上述特征的配体L和A通过至少一个化学键互连，形成一个共用四齿配体。
4.权利要求3的络合物，其中配体L符合式II：
D1-G-D2 (II)
其中G代表二价有机桥连基或直接键，且
D1和D2各自独立地代表含有选自氮、硫和/或磷的给电子杂原子的有机残基；和/或
其中配体A符合式III：
D3-G’-D4 (III)
其中G′代表有机桥连基或直接键，
D3代表含有选自氮、氧、硫、磷的给电子杂原子的有机残基，且
D4代表含有选自氮、硫的阴离子杂原子的有机残基。
5.权利要求4的络合物，其中配体A符合式IV：
其中
Z是与氮原子一起形成不饱和或芳族4元至8元环的有机桥连基，其任选地可以被取代，且
Y-是通过阴离子氮与中心Cu原子结合的脂族或芳族、环状或非环状的有机残基，且
其中优选地
G′代表直接键；
D3代表具有5至14个环原子的不饱和或芳族杂环残基，例如叔芳族氨基残基或相应的氧杂或硫杂残基；
D4代表具有5至14个环原子的不饱和或芳族N-杂环残基的阴离子；
或其中配体D3-G’-D4代表符合式V的由具有8至14个环原子的至少2个稠合的环构成的体系：
其任选地可以被取代，其中Z′是含有至少一个选自氮、氧、硫、磷的给电子杂原子、并和与其键合的碳原子一起形成不饱和或芳族4元至8元环的有机桥连基，其任选地可以被取代；且其中Z和Z″独立地选自与氮原子一起构成不饱和或芳族4元至8元环的有机桥连基和直接键，其任选地可以被取代，并且其中Z和Z″的至少一个不是直接键。
6.权利要求4的络合物，其中：
D3选自吡啶基、嘧啶基、哒嗪基、吡唑基、吡喃基、香豆素基、蝶啶基、苯硫基、苯并苯硫基、呋喃基、苯并呋喃基、噻唑基、噻吩并噻吩基、二硫代吲丹烯基、喹啉基、异喹啉基、喹喔啉基、吖啶基、氮杂萘基、菲酚基、三嗪基、噻吩基、
它们各自是未取代的或取代的；且
D4是在残基嘌呤基、吡咯基、吲哚基、咔唑基、三唑基、苯并三唑基、吡唑基、苯并吡唑基、咪唑基、苯并咪唑基、四唑基的N-脱质子化后可获得的阴离子残基，它们各自是未取代的或取代的；
或者其中配体D3-G’-D4具有式V，其中Z′是与2个连接碳原子键合的有机桥连基，并选自NCHCHCH、CHNCHCH、NNCHCH、NCHNCH、NCHCHN、NNNCH、NNCHN、OCHCH、CHOCH、OCHN、SCHCH、SCHN、CHSCH，它们的碳原子可任选被取代；且Z″-N--Z是与2个连接碳原子键合的有机桥连基，并且选自N-CHCH、CHN-CH、N-CHN、N-NCH、N-NN，它们的碳原子如果存在可任选被取代；
特别地，其中来自D3或Z′的杂原子以及阴离子氮在1，3位或1，4位或1，5位。
7.权利要求4的络合物，其中配体L符合式II：
D1-G-D2 (II)
其中G代表选自C1-C8亚烷基、C2-C8亚烯基、C2-C8亚炔基、O、S、SO、SO2、O插入的C2-C6亚烷基、亚苯基、取代的亚苯基的二价有机桥连基，或代表直接键；且
D1和D2各自独立地选自式VI的氧膦基残基和D3：
P(D5)(D6)D7- (VI)
其中D3是具有5至14个环原子的不饱和或芳族N-杂环残基，例如叔芳族氨基残基；D3优选选自吡啶基、嘧啶基、哒嗪基、吡唑基、吡喃基、香豆素基、蝶啶基、苯硫基、苯并苯硫基、呋喃基、苯并呋喃基、噻唑基、噻吩并噻吩基、二硫代吲丹烯基、喹啉基、异喹啉基、喹喔啉基、吖啶基、氮杂萘基、菲酚基、三嗪基、噻吩基、它们各自是未取代的或取代的；
D5和D6独立地是C1-C8烷基、C2-C8链烯基、C2-C8链炔基、或优选C4-C10芳基，例如苯基，它们各自是未取代的或取代的；且
D7是C1-C8亚烷基、C2-C8亚烯基、C2-C8亚炔基、或优选C4-C10亚芳基，例如亚苯基，它们各自是未取代的或取代的；
特别地，其中给电子杂原子在1，4位、1，5位、1，6位、1，7位、1，8位或1，9位。
8.根据前述权利要求任一项的络合物，其中如果存在任何取代基，其选自C1-C18烷氧基；C1-C18烷基；被卤素、OH、COOH或CONH2取代的所述烷基或烷氧基；被O、S、COO或CONH插入的所述烷基或烷氧基；C2-C8链烯基；C2-C8炔基；C4-C12环烷氧基；C4-C12环烷基；OH；COOH；卤素；C1-C14芳基，例如苯基或萘基；被C1-C8烷基、C1-C8烷氧基、C1-C8卤烷基、C2-C8链烯基、C2-C8炔基、C1-C8烷氧基羰基、C1-C8烷酰氧基、硝基、卤素、OH、COOH、CONH2取代的所述芳基；其中饱和碳也可以被氧代(＝O)取代，相邻的取代基可连接到一起以例如形成碳环、内酯、酸酐、环醚，例如氧杂环丁烷或氧杂环丙烷，或酰亚胺环。
9.有机电子器件，尤其是有机发光二极管或发光电池，其包含发光层，其中该发光层包含根据权利要求1至8任一项的化合物。
10.权利要求9的器件，进一步包含空穴传输材料，尤其选自聚乙烯基咔唑、N，N′-二苯基-N，N′-双(3-甲基苯基)-[1，1′-联苯基]-4，4′-二胺(TPD)、1，1-双[(二-4-甲苯基氨基)苯基]环己烷(TAPC)、N，N′-双(4-甲基苯基)-N，N′-双(4-乙基苯基)-[1，1′-(3，3′-二甲基)联苯基]4，4′-二胺(ETPD)、四-(3-甲基苯基)-N，N，N ′，N′-2，5-亚苯基二胺(PDA)、a-苯基-4-N，N-二苯基氨基苯乙烯(TPS)、对-(二乙基氨基)苯甲醛二苯基腙(DEH)、三苯胺(TPA)、双[4-(N，N-二乙基氨基)-2-甲基苯基](4-甲基苯基)甲烷(MPMP)、1-苯基-3-[对-(二乙基氨基)苯乙烯基]-5-[对-(二乙基氨基)苯基]吡唑啉(PPR或DEASP)、1，2-反式-双(9H-咔唑-9-基)环丁烷(DCZB)、N，N，N′，N′-四(4-甲基苯基)-(1，1′-联苯基)-4，4′-二胺(TTB)、4，4’-N，N-二咔唑-联苯基(CBP)、N，N-二咔唑基-1，4-二亚甲基-苯(DCB)、卟啉化合物、(苯基甲基)聚硅烷、聚(3，4-亚乙二氧基噻吩)(PEDOT)、聚苯胺、及其组合，或掺入例如聚苯乙烯、聚碳酸酯的聚合物中的一种或多种上述组分。
11.根据权利要求1至8任一项的化合物在电子器件中的用途，尤其是用作有机发光二极管或发光电池中的活性组分、用作氧敏指示剂、用作pH敏感指示剂、用作生物鉴定中的磷光指示剂或用作催化剂。
12.制备发光器件、特别是有机发光二极管或发光电池的方法，该方法包括在基底上的一对电极之间提供有机物质层，该有机物质层含有根据权利要求1至8任一项的络合物或络合物盐。
13.含有根据权利要求9或10的有机发光二极管的器件，该器件选自固定和移动显示器，例如用于电脑、移动电话、手提电脑、pdas、电视机的显示器、在印刷机、厨房设备、广告板、照明设备、例如火车和公交车上的信息板和指路牌中的显示器。
14.下式的化合物：
其中
i和m独立地为0、1或2；
k为3至5；
R独立地为C1-C12烷基、C2-C8链烯基、卤素、硝基、氨基、甲氧基；
X是H、C1-C12烷基，或阳离子同等物，例如Li+、Na+、K+、1/2Ca2+、1/2Mg2+、1/2Zn2+。
15.权利要求14的3-吡啶基取代的1，2，4-三唑化合物的用途，用作用于制备过渡金属络合物的配体。
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103493236A (zh) * | 2011-04-08 | 2014-01-01 | 欧司朗光电半导体有限公司 | 光电子器件和铜络合物作为掺杂材料以用于对层进行掺杂的应用 |
| CN103797017A (zh) * | 2011-07-08 | 2014-05-14 | 辛诺拉有限公司 | 用于光电设备的铜(i)配合物 |
| CN102899029A (zh) * | 2012-09-04 | 2013-01-30 | 中国计量学院 | 一种碘化亚铜基配合物发光材料及其制备方法 |
| CN103130841A (zh) * | 2013-03-25 | 2013-06-05 | 南京工业大学 | 一种5-(萘啶-4-基)三氮唑衍生物过渡金属配合物与发光应用 |
| CN110746602A (zh) * | 2019-10-29 | 2020-02-04 | 大连理工大学 | 一种金属钴卟啉基多孔有机聚合物及其制备方法和应用 |
| CN112358500A (zh) * | 2020-11-09 | 2021-02-12 | 江西科技师范大学 | 一种具有高摩尔吸光系数的Cu(I)配合物发光材料 |
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| EP2170911A2 (en) | 2010-04-07 |
| WO2009000673A3 (en) | 2009-02-19 |
| KR101539789B1 (ko) | 2015-07-27 |
| US20100252820A1 (en) | 2010-10-07 |
| WO2009000673A2 (en) | 2008-12-31 |
| EP2170911B1 (en) | 2018-11-28 |
| KR20100052458A (ko) | 2010-05-19 |
| US8440826B2 (en) | 2013-05-14 |
| CN101720330B (zh) | 2017-06-09 |
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