CN107074765B - 用于有机光电器件的有机分子 - Google Patents
用于有机光电器件的有机分子 Download PDFInfo
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- CN107074765B CN107074765B CN201680003325.2A CN201680003325A CN107074765B CN 107074765 B CN107074765 B CN 107074765B CN 201680003325 A CN201680003325 A CN 201680003325A CN 107074765 B CN107074765 B CN 107074765B
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- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
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- 238000000628 photoluminescence spectroscopy Methods 0.000 description 1
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- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
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- 238000011069 regeneration method Methods 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
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- WSFTWAORPPESCI-UHFFFAOYSA-N triphenyl(thiophen-2-yl)silane Chemical compound C1=CSC([Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 WSFTWAORPPESCI-UHFFFAOYSA-N 0.000 description 1
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- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
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Images
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- 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
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- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- C07D279/26—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom without other substituents attached to the ring system
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- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
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- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- 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
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- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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Abstract
本发明涉及精确具有通过单键或桥基Y相互连接的两个根据式I的单元的有机分子,其中Y=二价化学基团;X=在每次出现时相同或不同地为CN或CF3;D=具有式I‑1结构的化学单元:其中#=式I‑1的单元与根据式I的结构的连接点;A和B=彼此独立地选自由CRR1、CR、NR、N组成的组,其中在A和B之间存在单键或双键以及在B和Z之间存在单键或双键;Z=直接键或二价有机桥基,所述二价有机桥基为取代或未取代的C1‑C9‑亚烷基、C2‑C8‑亚烯基、C2‑C8‑亚炔基或亚芳基或其组合,‑CRR1、‑C=CRR1、‑C=NR、‑NR‑、‑O‑、‑SiRR1‑、‑S‑、‑S(O)‑、‑S(O)2‑、氧间隔的取代或未取代的C1‑C9‑亚烷基、C2‑C8‑亚烯基、C2‑C8‑亚炔基或亚芳基、苯基或取代的苯基单元。
Description
技术领域
本发明涉及纯有机分子及其在有机发光二极管(OLED)和其它有机光电器件中的用途。
背景技术
有机光电器件的特征是将电能转换成光子(有机发光二极管,OLED或发光电化学电池,LEEC)或发生相反过程(有机光伏,OPV)。此处重要的是,这些过程尽可能高效地运行。因此,对于OLED的部分,理想地使用具有最大光致发光量子产率的材料是必要的。通过使用显示出热活化延迟荧光(TADF)的有效材料可以改进OLED材料的有限效率,因为与纯荧光材料相比,可以利用高达100%的激子,而不是在OLED中形成的25%的激子。形成的三线态激子在这种情况下也可以转换成单线态激子,即随后可发出光子的状态。这种热再生的前提条件是最低激发单重态能级(S1)和三重态能级(T1)之间的低能量距离。这可以例如通过使用铜(I)配合物(在这方面参见例如:H.Yersin,U.Monkowius,T.Fischer,T.Hofbeck,WO2010/149748 A1)实现,或者通过纯的有机材料的方法(在这方面参见例如:Q.Zhang等人,J.Am.Chem.Soc.2012,134,14706,WO 2013161437 A1)。
还存在对新材料的大量需求,例如对于深蓝色TADF OLED。现有的蓝色TADF材料通常显示出高的激子寿命,这对于有效和长寿命的OLED是不利的。除了材料的上述性质以外,它们的可用性也与商业化有关。这包括合成结构单元的可用性,以及功能材料的实际合成的成本和便利,特别是包括该材料的纯化。
发明内容
本发明提供新类别的分子,其精确含有两个式I的单元,即第一个式I的单元和第二个式I的单元。
两个式I的单元经由单键彼此连接(因而苯环经由单键直接彼此键合),或者通过由R'和/或R”形成的桥基Y彼此连接,单键或桥基Y可选地经由第一个式I的单元的R'和第二个式I的单元的R'、或经由第一个式I的单元的R”和第二个式I的单元的R'、或经由第一个式I的单元的R'和第二个式I的单元的R”、或经由第一个式I的单元的R”和第二个式I的单元的R”来形成。这意味着桥基Y连接到位置R'和/或R”,或者单键各自地存在于两个式I的单元的两个位置R'和/或R”之间。
在式I中
Y=任意的二价化学基团;
X=在每次出现时相同或不同地为CN或CF3;
D=具有式I-1的结构的化学单元:
其中
#=式I-1单元与式I的结构的附着点;
A和B=彼此独立地选自由CRR1、CR、NR、N组成的组,在A和B之间存在单键或双键以及在B和Z之间存在单键或双键;
Z=直接的键或二价有机桥基,该二价有机桥基为取代或未取代的C1-C9-亚烷基、C2-C8-亚烯基、C2-C8-亚炔基或亚芳基或其组合,-CRR1、-C=CRR1、-C=NR、-NR-、-O-、-SiRR1-、-S-、-S(O)-、-S(O)2-、O-间隔的取代或未取代的C1-C9-亚烷基、C2-C8-亚烯基、C2-C8-亚炔基或亚芳基、苯基单元或取代的苯基单元;
其中每个R和R1在每次出现时相同或不同地为H、氘、叠氮化物(N3 -)、F、Cl、Br、I、N(R2)2、CN、CF3、NO2、OH、COOH、COOR2、CO(NR2)2、Si(R2)3、B(OR2)2、C(=O)R2、P(=O)(R2)2、S(=O)R2、S(=O)2R2、OSO2R2、具有1至40个C原子的直链烷基、烷氧基或硫代烷氧基,或具有2至40个C原子的直链烯基或炔基,或具有3至40个C原子的支链或环状烷基、烯基、炔基、烷氧基或硫代烷氧基,在各情况下可以被一个或多个基团R2取代,一个或多个不相邻的CH2基团可以被R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S或CONR2代替,并且一个或多个H原子可以被氘、F、Cl、Br、I、CN、CF3或NO2代替,或者是具有5至60个芳族环原子的芳族或杂芳族环体系,该环体系可以在各情况下被一个或多个基团R2取代,或者是具有5至60个芳族环原子的芳氧基或杂芳氧基,该基团可以被一个或多个基团R2取代,或者是具有10至40个芳族环原子的二芳基氨基、二杂芳基氨基或芳基杂芳基氨基,该基团可以被一个或多个基团R2取代,或者是这些体系的组合,或是可交联单元QE,其可以在存在或不存在光引发剂的情况下通过酸催化、热或UV交联方法或者通过微波辐射交联;这些取代基R和R1中的两个或更多个可以彼此形成单环或多环,脂族,芳族和/或苯并稠合的环体系;
R2,在每次出现时相同或不同地为H、氘、F、Cl、Br、I、N(R3)2、CN、CF3、NO2、OH、COOH、COOR3、CO(NR3)2、Si(R3)3、B(OR3)2、C(=O)R3、P(=O)(R3)2、S(=O)R3、S(=O)2R3、OSO2R3,具有1至40个C原子的直链烷基、烷氧基或硫代烷氧基,或具有2至40个C原子的直链烯基或炔基,或具有3至40个C原子的支链或环状烷基、烯基、炔基、烷氧基或硫代烷氧基,在各情况下可以被一个或多个基团R3取代,一个或多个不相邻的CH2基团可以被R3C=CR3、C≡C、Si(R3)2、Ge(R3)2、Sn(R3)2、C=O、C=S、C=Se、C=NR3、P(=O)(R3)、SO、SO2、NR3、O、S或CONR3代替,并且一个或多个H原子可以被氘、F、Cl、Br、I、CN、CF3或NO2代替,或者是具有5至60个芳族环原子的芳族或杂芳族环体系,该环体系可以在各情况下被一个或多个基团R3取代,或者是具有5至60个芳族环原子的芳氧基或杂芳氧基,该基团可以被一个或多个基团R3取代,或者是具有10至40个芳族环原子的二芳基氨基、二杂芳基氨基或芳基杂芳基氨基,该基团可以被一个或多个基团R3取代,或者是这些体系的组合;这些取代基R2中的两个或更多个可以彼此形成单环或多环,脂族,芳族和/或苯并稠合的环体系;
R3,在每次出现时相同或不同地为H、氘、F、CF3或具有1至20个C原子的脂族、芳族和/或杂芳族烃基,其中一个或多个H原子也可以被F或CF3代替;两个或更多个取代基R3可以彼此形成单环或多环、脂族环体系;
R'=第二个式I的单元的附着位置或选自由以下组成的组:Y,H,N(R4)2,OR4,具有1至40个C原子的直链烷基或烷氧基或具有3至40个C原子的支链或环状烷基或烷氧基,该基团在各情况下可以被一个或多个基团R4取代,和具有5至60个芳族环原子的芳族或杂芳族环体系,该体系在各情况下被一个或多个基团R4取代;
R”=第二个式I的单元的附着位置或选自由以下组成的组:Y,N(R4)2,OR4,具有1至40个C原子的直链烷基或烷氧基或具有3至40个C原子的支链或环状烷基或烷氧基,该基团在各情况下可以被一个或多个基团R4取代,和具有5至60个芳族环原子的芳族或杂芳族环体系,该体系在各情况下被一个或多个基团R4取代;
条件是如果R'为Y,则R”不为Y,并且如果R”为Y,则R'不为Y;
并且条件是如果R'是第二个式I的单元的附着位置,则R”不是第二个式I的单元的附着位置,并且如果R”是第二个式I的单元的附着位置,则R'不是第二个式I的单元的附着位置;
R4,在每次出现时相同或不同地为H、氘、N(R5)2、Si(R5)3、具有1至40个C原子的直链烷基、烷氧基或硫代烷氧基或具有3至40个C原子的支链或环状烷基、烷氧基或硫代烷氧基,该基团在各情况下可以被一个或多个基团R5取代,或者是具有5至60个芳族环原子的芳族或杂芳族环体系,该系在各情况下可以被一个或多个基团R5取代,或者是具有5至60个芳族环原子的芳氧基或杂芳氧基,该基团可以被一个或多个基团R5取代,或者是具有10至40个芳族环原子的二芳基氨基、二杂芳基氨基或芳基杂芳基氨基,该基团可以被一个或多个基团R5取代,或者是这些体系的组合;这些取代基R5中的两个或更多个可以彼此形成单环或多环、脂族、芳族和/或苯并稠合的环体系;
R5,在每次出现时相同或不同地为H、氘或具有1至20个C原子的脂族,芳族和/或杂芳族烃基;两个或更多个取代基R5还可以彼此形成单环或多环脂族环体系。
在另一个实施方案中,R'为H,R”为第二个式I的单元的附着点或者为Y。
在另一个实施方案中,R'选自由以下组成的组:Y、H、N(R4)2、OR4、具有1至40个C原子的直链烷基或烷氧基或具有3至40个C原子的支链或环状烷基或烷氧基,该基团在各情况下可以被一个或多个基团R4取代,以及具有5至60个芳族环原子的芳族或杂芳族环体系,该环体系在各情况下可以被一个或多个基团R4取代,和
R”选自由以下组成的组:Y、N(R4)2、OR4、具有1至40个C原子的直链烷基或烷氧基或具有3至40个C原子的支链或环状烷基或烷氧基,该基团在各情况下可以被一个或多个基团R4取代,以及具有5至60个芳族环原子的芳族或杂芳族环体系,该环体系在各情况下可以被一个或多个基团R4取代;
条件是如果R'为Y,则R”不为Y,并且如果R”为Y,则R'不为Y;
在一个实施方案中,R'=第二个式I的单元的附着位置或选自由以下组成的组:Y、H、N(R4)2、OR4、可被一个或多个基团R4取代的噻吩、具有1至40个C原子的直链烷基或烷氧基或具有3至40个C原子的支链或环状烷基或烷氧基,该基团在各情况下可以被一个或多个基团R4取代,和具有5至60个芳族环原子的芳族环体系,该环体系可以被一个或多个基团R4取代;
和R”=第二个式I的单元的附着位置或选自由以下组成的组:Y、N(R4)2、OR4、可被一个或多个基团R4取代的噻吩,具有1至40个C原子的直链烷基或烷氧基或具有3至40个C原子的支链或环状烷基或烷氧基,该基团在各情况下可以被一个或多个基团R4取代,和具有5至60个芳族环原子的芳族环体系,该环体系可以被一个或多个基团R4取代;
条件是如果R'为Y,则R”不为Y,并且如果R”为Y,则R'不为Y;
并且条件是如果R'是第二个式I的单元的附着位置,则R”不是第二个式I的单元的附着位置,并且如果R”是第二个式I的单元的附着位置,则R'不是第二个式I的单元的附着位置;
其中Y和R4如上文所定义。
在一个实施方案中,R'=第二个式I的单元的附着位置或选自由以下组成的组:Y、H、N(R4)2、OR4、具有1至40个C原子的直链烷基或烷氧基或具有3至40个C原子的支链或环状烷基或烷氧基,该基团在各情况下可以被一个或多个基团R4取代,和具有5至60个芳族环原子的芳族或杂芳族环体系,该环体系在各情况下可以被一个或多个基团R4取代;
和R”=第二个式I的单元的附着位置或选自由以下组成的组:Y、N(R4)2、OR4、具有1至40个C原子的直链烷基或烷氧基或具有3至40个C原子的支链或环状烷基或烷氧基,该基团在各情况下可以被一个或多个基团R4取代,和具有5至60个芳族环原子的芳族或杂芳族环体系,该环体系在各情况下可以被一个或多个基团R4取代;
条件是杂芳族环体系不是N-杂芳族;
并且条件是如果R'为Y,则R”不为Y,并且如果R”为Y,则R'不为Y;
并且条件是如果R'是第二个式I的单元的附着位置,则R”不是第二个式I的单元的附着位置,并且如果R”是第二个式I的单元的附着位置,则R'不是第二个式I的单元的附着位置;
其中Y和R4如上文所定义。
在本发明意义上的芳基含有6至60个芳族环原子;在本发明意义上的杂芳基含有5至60个芳族环原子,其中至少一个表示杂原子。杂原子优选为N,O和/或S。这是基本定义。如果在本发明的说明书中陈述了其它优选,例如关于存在的芳族环原子或杂原子的数目,则这些适用。
本文的芳基或杂芳基分别为简单的芳环即苯,或简单的杂芳环如吡啶、嘧啶或噻吩,或杂芳族多环体系,例如菲、喹啉或咔唑。在本专利申请意义上的稠合(融合)芳族或杂芳族多环体系由两个或更多个彼此融合的简单芳族和/或杂芳族环组成。
在各情况下可以被上述基团取代并且可以通过芳族或杂芳族部分上的任何所需位置连接的芳基或杂芳基特别理解为指衍生自以下的基团:苯、萘、蒽、芘、二氢芘、(chrysene)、苝、荧蒽、苯并蒽、苯并菲、并四苯、并五苯、苯并芘、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、异喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、吩噻嗪、吩噁嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、噁唑、苯并噁唑、萘并噁唑、蒽噻唑、菲咯噁唑、异噁唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、吡嗪、吩嗪、萘啶、氮杂咔唑、苯并喹啉、菲咯啉、1,2,3-***、1,2,4-***、苯并***、1,2,3-噁二唑、1,2,4-噁二唑、1,2,5-噁二唑、1,2,3,4-四嗪、嘌呤、蝶啶、中氮茚和苯并噻二唑或这些基团的组合。
在本发明意义上的环状烷基、烷氧基或硫代烷氧基是指单环、双环或多环基团。
出于本发明的目的,其中各个H原子或CH2基团也可以被上述基团取代的C1-至C40-烷基是指例如基团甲基、乙基、正丙基、异丙基、环丙基、正丁基、异丁基、仲丁基、叔丁基、环丁基、2-甲基丁基、正戊基、仲戊基、叔戊基、2-戊基、新戊基、环戊基、正己基、仲己基、叔己基、2-己基、3-己基、新己基、环己基、1-甲基环戊基、2-甲基戊基、正庚基、2-庚基、3-庚基、4-庚基、环庚基、1-甲基环己基、正辛基、2-乙基己基、环辛基、1-二环[2.2.2]辛基、2-二环[2.2.2]辛基、2-(2,6-二甲基)辛基、3-(3,7-二甲基)辛基、金刚烷基、三氟甲基、五氟乙基、2,2,2-三氟乙基、1,1-二甲基-正己-1-基、1,1-二甲基-正庚-1-基-、1,1-二甲基-正辛-1-基-、1,1-二甲基-正癸-1-基、1,1-二甲基-正十二烷-1-基-、1,1-二甲基-正十四烷-1-基-、1,1-二甲基-正十六烷-1-基-、1,1-二甲基-正十八烷-1-基-、1,1-二乙基-正己-1-基、1,1-二乙基-正庚-1-基-、1,1-二乙基-正辛-1-基-、1,1-二乙基-正癸基-1-基-、1,1-二乙基-正十二烷-1-基-、1,1-二乙基-正十四烷-1-基-、1,1-二乙基-正十六烷-1-基-、1,1-二乙基-正十八烷-1-基-、1-(正丙基)-环己-1-基-、1-(正丁基)-环己-1-基-、1-(正己基)-环己-1-基-、1-(正辛基)-环己-1-基-、和1-(正癸基)-环己-1-基。烯基是指例如乙烯基、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、环辛烯基或环辛二烯基。炔基是指例如乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基或辛炔基。C1-至C40-烷氧基是指例如甲氧基、三氟甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基或2-甲基丁氧基。
本发明分子中的化学单元D具有供体性质。技术人员从原理上分别意识到供体和受体性质。在一个优选的实施方案中,化学单元D是供电子的。它具有+M效应(正介电效应)。特别地,合适的供体取代基具有带有自由电子对的原子,例如N,O或S原子。本文中优选具有正好一个环杂原子的5元环杂芳基。这些杂芳基还可以具有与它们稠合的其它芳基。在本文中特别优选的是咔唑基或咔唑衍生物。其它合适的供体取代基是吩噁嗪基团或吩噁嗪衍生物。在后者的情况下,吩噁嗪的氧可以被例如-CRR1、-C=CRR1、-C=NR、-NR-、-SiRR1-、-S-、-S(O)-、-S(O)2-、O-间隔的取代或未取代的C1-C9-亚烷基、C2-C8-亚烯基、C2-C8-亚炔基或亚芳基、苯基单元或取代的苯基单元代替。
在一个优选的实施方案中,吸电子基团X发挥-M效应(负介电效应)或-I效应(负诱导效应)。因此,基团X是受体取代基。合适的受体取代基特别为氰基或CF3。
在芳族部分上的供体的邻位,本发明的分子具有取代基。这允许有机分子的HOMO和LUMO的有效分离。
本发明的分子显示出热活化延迟荧光,并优选在可见光谱的深蓝色区域发射。
本发明的分子在光电器件如OLED中的使用导致器件部分的更高的效率。此外,可以实现深蓝色光谱中的OLED。相应的OLED比具有已知发射体材料和相当颜色的OLED具有更大的稳定性。
在一个实施方案中,可交联单元QE包含选自氧杂环丁烷、炔烃和叠氮化物组成的组的化合物,更特别地用于点击反应(click reaction),以及以下烯烃衍生物:
在可选的实施方案中,Z是共价单键或选自取代和未取代的亚烷基(包括支链或环状)、亚烯基、亚炔基、亚芳基和杂亚芳基、O、NR、C=CR2、C=NR、SiR2、S、S(O)、S(O)2、BR、PR、P(O)R,以及可能这些基团的组合(例如O-间隔的亚烷基(包括支链或环状)、亚烯基、亚炔基、亚芳基和亚杂芳基)的二价有机桥。
在一个优选的实施方案中,彼此独立的D在各情况下是具有供电子性质的供体基团,其选自由以下组成的组:取代和未取代的咔唑、取代或未取代的吲哚、取代和未取代的二氢吲哚、取代和未取代的二氢吖啶、取代和未取代的苯并咪唑、取代和未取代的2,3,4,9-四氢咔唑、取代和未取代的1,2,3,4-四氢喹啉、取代和未取代的吩噻嗪、取代和未取代的吩噁嗪、取代和未取代的二氢吩嗪、取代和未取代的螺环化合物。
在有机分子的一个实施方案中,具有式I-1的供电子性质的供体基团具有式II的结构:
其中#、Z和R的定义如上文关于式I所述。
在一个实施方案中,具有式I-1的供电子性质的供体基团可以具有式III的结构:
其中#和R的定义如上文关于式I所述。
本发明的供体的实例:
式I的接受单元X在一个实施方案中为CN,在另一个实施方案中为CF3。在本发明的另一个实施方案中,式I的基团R'是氢原子,即H。
二价基团Y是有机桥,其在一个实施方案中是取代或未取代的亚烷基、亚烯基、亚炔基、亚芳基或亚杂芳基或其组合,或是-O-、-NR-、-C=CR2、-C=NR、-SiR2-、-S-、-S(O)-、-S(O)2-、O-间隔的烷基(包括支链或环状)、杂烷基、芳基、杂芳基、烯基、苯基单元和取代的苯基单元;R的定义如上所述。
桥基Y可以选自例如式IV至X的结构之一:
其中
#=桥基Y与式I的结构的附着点(即分别标记有R'和/或R”的第一个和第二个式I的单元的位置)。
在一些实施方案中,本发明的分子具有式XI-a、XI-b或XI-c的结构:
其中n=0或1;
并且其中D、R'、R”、X和Y的定义如上所述。
在一个实施方案中,本发明的分子具有式XII的结构。
并且其中D、R'和X的定义如上所述。
在另一个优选的实施方案中,本发明的分子具有式XIII的结构:
其中D和X的定义如上所述。
在另一方面,本发明涉及用于制备本文所述类型的本发明的有机分子的方法。
所示合成是对于本发明的在苯环之间具有单键的分子,以及对于通过桥基Y的键,在各情况下具有至少一个任选的后续反应。
在这种情况下,氮杂环在亲核芳香取代中与芳基卤化物,优选芳基氟化物反应。典型的条件包括例如在非质子极性溶剂如二甲基亚砜(DMSO)或N,N-二甲基甲酰胺(DMF)中使用碱,如磷酸三钾或氢化钠。
可选的合成途径包括通过铜或钯催化引入氮杂环,偶联到芳基卤或芳基类卤化物,优选芳基溴、芳基碘、芳基三氟甲磺酸酯或芳基甲苯磺酸酯。
所述的制备模式可以表示最后的合成反应,亦或是提供前体分子,其可以通过后续反应例如通过改变基团R、R'和/或R”转换成本发明的分子。
本发明的另一方面涉及本文所述类型的有机分子在有机光电器件中作为发光发射体或作为吸收剂和/或作为主体材料和/或作为电子输送材料和/或作为空穴注射材料和/或作为作为空穴阻挡材料的用途。
在这种用途的上下文中,有机光电器件更特别地选自由以下组成的组:
·有机发光二极管(OLED),
·发光电化学电池,
·OLED传感器,特别是非密封外部屏蔽的气体和蒸气传感器,
·有机二极管,
·有机太阳能电池,
·有机晶体管,
·有机场效应晶体管,
·有机激光器和
·下变频元件(down-conversion element)。
在使用的情况下,在有机光电器件中,更具体地在OLED中,有机分子在发射层中的分数为1%至99%,更特别地为5%至80%(重量%)。在可选的实施方案中,有机分子在发射层中的比例为100%。
在一个实施方案中,发光层不仅包括本发明的有机分子,而且还包括三重态(T1)和单重态(S1)能级高于有机分子的三重态(T1)和单重态(S1)能级的主体材料。
在另一方面,本发明涉及一种有机光电器件,其包括本文所述类型的有机分子,更具体地以选自由以下组成的组的器件的形式:有机发光二极管(OLED)、发光电化学电池、OLED传感器、更特别地是非密封外部屏蔽的气体和蒸气传感器、有机二极管、有机太阳能电池、有机晶体管、有机场效应晶体管、有机激光器和下变频元件。
在一个实施方案中,这种类型的有机光电器件具有:
-基材,
-阳极和
-阴极,阳极或阴极特别地直接施加到基材上,和
-至少一个发光层,其设置在阳极和阴极之间,并且包括本发明的有机分子。
在一个实施方案中,光电器件是OLED。典型的OLED具有例如以下层构造:
1.基材(支承材料)
2.阳极
3.空穴注射层(HIL)
4.空穴输送层(HTL)
5.电子阻挡层(EBL)
6.发射层(EML)
7.空穴阻挡层(HBL)
8.电子输送层(ETL)
9.电子注射层(EIL)
10.阴极。
一些层仅任选地存在。此外,这些层中的多个可以彼此同时存在。并且一些层可以在组件中多次存在。
根据一个实施方案,有机组件的至少一个电极在形式上是半透明的。在此处和下文中,“半透明”表示对可见光透射的层。该半透明层可以是透明清晰的即透明的,或者可以是至少部分光吸收的和/或部分光散射的,使得半透明层也可以例如具有漫射或乳状半透明。特别地,本文中被识别为半透明的层在形式上尽可能透明,因此,特别地,光的吸收尽可能小。
根据另一实施方案,有机组件,更具体地OLED,具有逆变器结构。逆变器结构的特征在于,阴极位于基材上,并且其它层相应地以相反的顺序施加:
1.基材(支承材料)
2.阴极
3.电子注射层(EIL)
4.电子输送层(ETL)
5.空穴阻挡层(HBL)
6.发射层(EML)
7.电子阻挡层(EBL)
8.空穴输送层(HTL)
9.空穴注射层(HIL)
10.阳极
一些层仅任选地存在。此外,这些层中的多个可以彼此同时存在。并且一些层可以在组件中多次存在。
在一个实施方案中,在倒转的OLED的情况下,典型构造的阳极层,例如ITO层(氧化铟锡)作为阴极连接。
根据另一实施方案,有机组件,更特别地是OLED,具有堆垛构造。在这种情况下,各个OLED彼此上下排列,而不是以通常的形式彼此并排排列。堆垛构造可允许混合光的产生。该构造可以用于例如产生白光,白光由通常通过来自蓝色,绿色和红色发射器发射的光的组合对整个可见光谱成像而产生。此外,对于几乎相同的效率和相同的亮度,与常规OLED相比可以实现明显更长的寿命。对于堆垛构造,任选地,在两个OLED之间使用称为电荷产生层(CGL)的层。该层由n-掺杂层和p-掺杂层组成,n-掺杂层通常更靠近阳极施加。
在一个实施方案中——称为串联OLED——在阳极和阴极之间存在两个或更多个发射层。在一个实施方案中,三个发射层一个在另一个之上排列,其中一个发射层发射红光,一个发射层发射绿光,一个发射层发射蓝光,并且任选地,在各个发射层之间施加另外的电荷产生层、阻挡层或输送层。在另一实施方案中,各发射层直接相邻地施加。在另一个实施方案中,在各发射层之间存在电荷产生层。也可以在OLED中将由电荷产生层分离的相邻的发射层和发射层直接组合。
在电极和有机层上,可以另外设置封装装置。封装装置可以例如以玻璃盖的形式或以薄膜封装的形式实现。
用作光电器件的支承材料可以是例如玻璃,石英,塑料,金属,硅晶片或任何其它合适的固体或柔性的、任选地透明的材料。
支承材料可以包括例如形式为层、膜、板或层压体的一种或多种材料。
用作光电器件的阳极可以是例如透明导电金属氧化物,例如ITO(氧化铟锡)、氧化锌、氧化锡、氧化镉、氧化钛、氧化铟或氧化铝锌(AZO)、Zn2SnO4、CdSnO3、ZnSnO3、MgIn2O4、GaInO3、Zn2In2O5或In4Sn3O12、或不同透明导电氧化物的混合物。
本文中用作HIL的材料可以是例如PEDOT:PSS(聚-3,4-亚乙基二氧噻吩:聚苯乙烯磺酸)、PEDOT(聚3,4-亚乙基二氧噻吩)、间-MTDATA(4,4',4”-三[苯基(间-甲苯基)氨基]三苯胺)、螺-TAD(2,2',7,7'-四(N,N-二苯基氨基)-9,9-螺二芴)、DNTPD(4,4'-双[N-[4-{N,N-双(3-甲基-苯基)氨基}苯基]-N-苯基氨基]联苯)、NPNPB(N,N'-二苯基-N,N'-二-[4-(N,N-二苯基-氨基)苯基]苯)、MeO-TPD(N,N,N',N'-四(4-甲氧基苯基)苯)、HAT-CN(1,4,5,8,9,11-六氮杂苯并菲六腈)、螺-NPD(N,N'-二苯基-N,N'-双(1-萘基)-9,9'-螺二芴-2,7-二胺)。
用作HTL的材料可以是叔胺、咔唑衍生物、聚苯乙烯磺酸掺杂聚乙烯二氧噻吩、樟脑磺酸掺杂聚苯胺、聚-TPD(聚(4-丁基苯基二苯胺))、[α]-NPD(聚(4-丁基苯基二苯胺))、TAPC(4,4'-亚环己基-双[N,N-双(4-甲基苯基)-苯胺])、TCTA(三(4-咔唑基-9-基苯基)胺)、2-TNATA(4,4',4”-三[2-萘基(苯基)氨基]三苯胺)、螺-TAD、DNTPD、NPNPB、MeO-TPD、HAT-CN或TrisPcz(9,9'-二苯基-6-(9-苯基-9H-咔唑-3-基)-9H,9'H-3,3'-二咔唑)。
HTL可以具有p-掺杂层,其在有机空穴传导基质中包括无机或有机掺杂剂。可以利用的无机掺杂剂的实例包括过渡金属氧化物,例如氧化钒、氧化钼或氧化钨。可以使用的有机掺杂剂包括例如四氟四氰基醌二甲烷(F4-TCNQ),五氟苯甲酸铜(Cu(I)pFBz)或过渡金属配合物。
用作电子阻挡层的材料可以是例如mCP(1,3-双(咔唑-9-基)苯)、TCTA、2-TNATA、mCBP(3,3-二(9H-咔唑-9-基)联苯)、三-Pcz(9,9'-二苯基-6-(9-苯基-9H-咔唑-3-基)-9H,9'H-3,3'-二咔唑)、CzSi(9-(4-叔丁基苯基)-3,6-双(三苯基甲硅烷基)-9H-咔唑)或DCB(N,N'-二咔唑基-1,4-二甲苯)。
发射层EML包括或由以下组成:发射体材料或包含至少两种发射体材料和任选的一种或多种主体材料的混合物。合适的主体材料的实例是mCP、TCTA、2-TNATA、mCBP、Sif87(二苯并[b,d]噻吩-2-基三苯基硅烷)、Sif88(二苯并[b,d]噻吩-2-基)二苯基硅烷)、CBP(4,4'-双-(N-咔唑基)联苯)或DPEPO(双[2-((氧代)二苯基膦基)苯基]醚)。对于以绿色或红色发射的发射体材料或者包括至少两种发射体材料的混合物,共同的基体材料例如CBP是合适的。对于以蓝色发射的发射体材料或包含至少两种发射体材料的混合物,可以使用UHG基体材料(超高能量间隙材料)(参见例如ME Thompson等人,Chem.Mater.2004,16,4743)或其它所谓的宽间隙基质材料。
空穴阻挡层HBL可以包括,例如,BCP(2,9-二甲基-4,7-二苯基-1,10-菲咯啉=深亚铜试剂(bathocuproin)),双(2-甲基-8-羟基喹啉)-(4-苯基苯酚)-铝(III)(BAlq),Nbphen(2,9-双(萘-2-基)-4,7-二苯基-1,10-菲咯啉),Alq3(铝-三(8-羟基喹啉)),TSPO1(二苯基-4-三苯基甲硅烷基苯基氧化膦)或TCB/TCP(1,3,5-三(N-咔唑基)苯/1,3,5-三(咔唑-9-基)苯)。
电子输送层ETL可以包括例如基于AlQ3、TSPO1、BPyTP2(2,7-二(2,2'-联吡啶-5-基)三苯基)或BTB(4,4'-双[2-(4,6-二苯基-1,3,5-三嗪基)]-1,1'-联苯)。
可用于薄电子注射层EIL的材料的实例包括CsF、LiF、8-羟基喹啉合锂(Liq)、Li2O、BaF2、MgO或NaF。
用作阴极层的材料可以是金属或合金,例如Al、Al>AlF、Ag、Pt、Au、Mg、Ag:Mg。典型的层厚度为100-200nm。特别优选例如通过薄的保护性氧化物层的形成来使用一种或多种在空气中稳定和/或自钝化的金属。
适于封装的材料的实例是氧化铝、氧化钒、氧化锌、氧化锆、氧化钛、氧化铪、氧化镧和氧化钽。
本领域技术人员知道用于包括本发明的有机分子的光电器件的材料的组合。
在本发明的有机光电器件的一个实施方案中,本发明的有机分子用作发光层中的发射材料,用作纯的层或与基质材料的组合。
在另一实施方案中,在发光层中的本发明的有机分子,在光学发光器件中更具体地在OLED中的发光层中的分数在5%和80%之间。在本发明的有机光电器件的一个实施方案中,将发光层施加到基材;优选地将阳极和阴极施加到基材并且将发光层施加在阳极和阴极之间。
发光层可以仅以100%浓度具有本发明的有机分子,其中将阳极和阴极施加到基材并且将发光层施加在阳极和阴极之间。
在本发明的有机光电器件的一个实施方案中,在阳极和阴极之间施加空穴注射层和电子注射层,并且在空穴注射层和电子注射层之间施加空穴输送层和电子输送层,并且在空穴输送层和电子输送层之间施加发光层。
在本发明的另一个实施方案中,有机光电器件包括以下:基材、阳极、阴极,以及在各情况下至少一个空穴注射层和电子注射层,以及在各情况下至少一个空穴输送层和电子输送层,和至少一个发光层,其包括本发明的有机分子和其三重态(T1)和单重态(S1)能级显著高于有机分子的三重态(T1)和单重态(S1)能级的主体材料,其中将阳极和阴极施加到基材,并且将空穴注射层和电子注射层施加在阳极和阴极之间,并且将空穴输送层和电子输送层施加在空穴注射层和电子注射层之间,在空穴输送层和电子输送层之间施加发光层。
根据本发明还提供一种包含本发明的有机分子和主体材料的发光材料,主体材料的三重态(T1)和单重态(S1)能级显著高于有机分子的三重态(T1)和单重态(S1)能级,其中发光材料发射荧光或热活化延迟荧光,并且在最低激发单重态(S1)状态和三重态(T1)状态之间具有小于3000cm-1的adeltaE(S1-T1)值。
在另一方面,本发明涉及一种用于制造光电组件的方法。在这种情况下使用本发明的有机分子。
在一个实施方案中,制备方法包括通过真空蒸发方法或从溶液中加工本发明的有机分子。
根据本发明,还提供一种用于制造包括至少一层光电器件的本发明的光电器件的方法:
-通过升华方法涂布,
-通过OVPD(有机气相沉积)方法涂布,
-通过载气升华涂布,和/或
-由溶液或通过印刷方法制备。
实施例
一般操作方案:光物理测量
光学玻璃的预处理
在每次使用后,清洁光学玻璃(由熔融石英制成的杯和基材,直径:1cm)。用二氯甲烷、丙酮、乙醇、软化水各洗涤三次。置于5%Hellmanex溶液中24小时,用软化水彻底冲洗,用氮气吹气以干燥光学玻璃。
样品制备:溶液
将1-2mg样品溶解在100ml的各溶剂中,浓度为10-5mol/l。将杯气密封闭并脱气10分钟。
样品制备,膜:旋涂
仪器:Spin150,SPS欧洲。
样品浓度为10mg/ml,在甲苯或氯苯中制备。
程序:1)在400rpm下3s;2)在1000rpm下以1000rpm/s 20秒;3)在4000rpm下以1000rpm/s 10s。涂布后,在来自LHG的精密热板上在70℃的空气中将膜干燥1分钟。
吸收光谱法
溶液:
在来自Thermo Scientific的Evolution 201仪器上记录UV-VIS光谱。(参见样品制备:溶液)
光致发光光谱法和TCSPC
使用来自Horiba Scientific的配备有150W氙弧灯、激发和发射单色器和Hamamatsu R928光电倍增管以及还具有TCSPC选项的FluoroMax-4荧光光谱仪进行稳态发射光谱法。使用标准校正曲线校正发射和激发光谱。
量子效率的确定
使用来自Hamamatsu Photonics的Absolute PL Quantum Yield MeasurementC9920-03G***测量光致发光量子产率。该***由150W氙气放电灯、可自动调节的Czerny-Turner单色仪(250–950nm)和具有高反射Spektralon(特氟龙衍生物)涂层的乌布利希球组成,通过玻璃纤维线缆连接到具有1024×122像素(尺寸24×24μm)的BT(背面变薄)CCD芯片的PMA-12多通道检测器。使用版本3.6.0的U6039-05软件分析量子效率和CIE坐标。
发射最大值以nm表示,量子产率Φ以%表示,CIE色度坐标以x,y值表示。
根据以下方案测定聚合物膜、溶液和粉末样品的PLQY:
使用的参考材料是在乙醇中的已知浓度的蒽。首先测定样品的最大吸收,并用于激发样品。随后在氮气气氛下对脱气的溶液和膜测定绝对量子产率。
该***自身根据以下等式使用光子数n光子和强度Int进行计算:
根据密度泛函理论的计算
使用BP86功能(Becke,A.D.Phys.Rev.A1988,38,3098–3100;Perdew,J.P.Phys.Rev.B1986,33,8822–8827),利用恒等分辨率(RI)近似(Sierka,M.;Hogekamp,A.;Ahlrichs,R.J.Chem.Phys.2003,118,9136–9148;Becke,A.D.,J.Chem.Phys.98(1993)5648-5652;Lee,C;Yang,W;Parr,R.G.Phys.Rev.B 37(1988)785-789)优化分子结构。在使用BP86通过使用B3LYP功能性的时间依赖性DFT(TD-DFT)方法优化结构的情况下计算激发能量(Becke,A.D.,J.Chem.Phys.98(1993)5648-5652;Lee,C;Yang,W;Parr,R.G.Phys.Rev.B 37(1988)785-789;Vosko,S.H.;Wilk,L.;Nusair,M.Can.J.Phys.58(1980)1200-1211;Stephens,P.J.;Devlin,F.J.;Chabalowski,C.F.;Frisch,M.J.J.Phys.Chem.98(1994)11623-11627)。所有计算使用def2-SV(P)库集(Weigend,F.;Ahlrichs,R.Phys.Chem.Chem.Phys.2005,7,3297–3305;Rappoport,D.;Furche,F.J.Chem.Phys.2010,133,134105/1–134105/11)和m4网格进行数字积分。所有DFT计算使用Turbomole程序包(版本6.5)(TURBOMOLE V6.42012,Karlsruhe University和Forschungszentrum Karlsruhe GmbH的研究,1989-2007,TURBOMOLE GmbH,自2007;http://www.turbomole.com)进行。
实施例1
阶段1:
将3-溴-4-氟三氟甲苯(65.8mmol)、双(频哪醇)二硼(32.9mmol)、Pd2(dba)3(0.33mmol)、SPhos(1.32mmol)和磷酸三钾(197mmol)在氮气下在110℃的二氧杂环己烷/水混合物(300ml/20ml)中搅拌16小时。随后通过过滤除去反应混合物的不溶性成分,用二氧杂环己烷洗涤过滤器上的物质。除去滤液的溶剂,将所得残余物溶于二氯甲烷中,并通过少量硅胶过滤。获得黄色固体状产物。1H NMR(500MHz,氯仿-d)δ=7.72-7.69(m,4H),7.34-7.31(m,2H)ppm。
阶段2:
将1a(5mmol),3,6-二甲氧基咔唑(12mmol)和磷酸三钾(20mmol)在氮气下悬浮于DMSO(20ml)中并在100℃下搅拌(16小时)。然后将反应混合物引入150ml水中,用二氯甲烷(2×100ml)萃取。将合并的有机相用饱和氯化钠溶液(2×150ml)洗涤,用硫酸镁干燥,然后除去溶剂。将粗产物吸收在二氯甲烷中并通过少量硅胶(洗脱液:二氯甲烷)过滤。最后,除去溶剂后,通过从乙醇和氯仿的混合物中的重结晶进行纯化。得到为白色固体的产物1。
1H NMR(500MHz,氯仿-d)δ8.15(d,J=2.1Hz,2H),7.59(dd,J=8.3,2.1Hz,2H),7.23(d,J=8.3Hz,3H),6.94(br s,2H),6.79-6.48(br m,4H),6.36(br s,2H),5.68(br s,2H),3.86(s,12H)。
可以在图1中看到1的膜发射(在PMMA中为10%)。发射最大值在461nm。光致发光量子产率(PLQY)为47%。
实施例2
阶段1:
将3-溴-4-氟苯腈(125mmol)、双(频哪醇)二硼(62.5mmol)、Pd2(dba)3(0.63mmol)、SPhos(2.50mmol)和磷酸三钾(375mmol)在氮气下在110℃的二氧杂环己烷/水混合物(350ml/20ml)中搅拌16小时。随后通过过滤除去反应混合物的不溶性成分,用二氧杂环己烷洗涤过滤器上的物质。除去滤液的溶剂,将所得残余物溶于四氢呋喃中,并通过少量硅胶过滤。获得黄色固体状产物。1H NMR(500MHz,氯仿-d)δ=7.79-7.76(m,2H),7.74-7.73(m,2H),7.36-7.33(m,2H)ppm。
阶段2:
将2a(8.33mmol),3,6-二甲氧基咔唑(19.2mmol)和磷酸三钾(33.3mmol)在氮气下悬浮于DMSO(30ml)中并在110℃下搅拌(16小时)。然后将反应混合物引入400ml饱和氯化钠溶液中,并用二氯甲烷(3×150ml)萃取。将合并的有机相用饱和氯化钠溶液(2×150ml)洗涤,用硫酸镁干燥,然后除去溶剂。最后,通过从甲苯中重结晶来纯化粗产物。获得为黄色固体的产物2。
1H NMR(500MHz,氯仿-d)δ=8.19(d,J=1.9Hz,2H),7.62(dd,J=8.3,2.0Hz,2H),7.24(d,J=8.3Hz,2H),7.21(br s,2H),6.87(br s,2H),6.72(br s,2H),6.49(br s,2H),6.38(br s,2H),5.65(br s,2H),3.94-3.75(m,12H)。
可以在图2中看到2的膜发射(在PMMA中为10%)。发射最大值在478nm。光致发光量子产率(PLQY)为75%。发射寿命为25μs。
实施例3
薄层色谱:Rf=0.5(环己烷/乙酸乙酯5:1)
可以在图3中看到3的膜发射(在PMMA中为10%)。发射最大值在495nm。光致发光量子产率(PLQY)为64%。发射寿命为13μs。
实施例4
薄层色谱:Rf=0.5(环己烷/乙酸乙酯5:1)
可以在图4中看到4的膜发射(在PMMA中为10%)。发射最大值在507nm。光致发光量子产率(PLQY)为66%。发射寿命为10μs。
实施例5
薄层色谱:Rf=0.5(环己烷/乙酸乙酯5:1)
可以在图5中看到5的膜发射(在PMMA中为10%)。发射最大值在450nm。光致发光量子产率(PLQY)为62%并且半峰全宽(FWHM)为64nm。
实施例6
薄层色谱:Rf=0.6(环己烷/乙酸乙酯10:1)
可以在图6中看到6的膜发射(在PMMA中为10%)。发射最大值在472nm。光致发光量子产率(PLQY)为32%。
实施例7
1H NMR(500MHz,氯仿-d)δ7.79(dd,J=8.2,2.0Hz,2H),7.63(d,J=2.0Hz,2H),7.48-7.32(m,6H),7.20-5.30(br m,J=510.3Hz,12H),1.87(s,6H),0.80(s,6H)。
可以在图7中看到7的膜发射(在PMMA中为10%)。发射最大值在471nm。光致发光量子产率(PLQY)为65%并且半峰全宽(FWHM)为83nm。发射寿命为21μs。
实施例8
测量8的膜发射(在PMMA中为10%)。发射最大值在461nm。光致发光量子产率(PLQY)为47%。半峰全宽(FWHM)为76nm。
实施例9
可以在图9中看到9的膜发射(在PMMA中为10%)。发射最大值在430nm。光致发光量子产率(PLQY)为23%。半峰全宽(FWHM)为76nm。
实施例10
可以在图10中看到10的膜发射(在PMMA中为10%)。发射最大值在434nm。光致发光量子产率(PLQY)为30%。半峰全宽(FWHM)为67nm。
实施例11
可以在图11中看到11的膜发射(在PMMA中为10%)。发射最大值在432nm。光致发光量子产率(PLQY)为42%。半峰全宽(FWHM)为62nm。
实施例12
测量12的膜发射(在PMMA中为10%)。发射最大值在441nm。光致发光量子产率(PLQY)为58%。半峰全宽(FWHM)为61nm。
实施例13
测量13的膜发射(在PMMA中为10%)。发射最大值在441nm。光致发光量子产率(PLQY)为48%。半峰全宽(FWHM)为66nm。
实施例14
测量14的膜发射(在PMMA中为10%)。发射最大值在433nm。光致发光量子产率(PLQY)为53%。半峰全宽(FWHM)为59nm。
实施例15
测量15的膜发射(在PMMA中为10%)。发射最大值在431nm。光致发光量子产率(PLQY)为21%。半峰全宽(FWHM)为68nm。
实施例16
测量16的膜发射(在PMMA中为10%)。发射最大值在448nm。光致发光量子产率(PLQY)为50%。半峰全宽(FWHM)为62nm。
实施例17
测量17的膜发射(在PMMA中为10%)。发射最大值在486nm。光致发光量子产率(PLQY)为61%。半峰全宽(FWHM)为91nm。
实施例18
测量18的膜发射(在PMMA中为10%)。发射最大值在442nm。光致发光量子产率(PLQY)为56%。半峰全宽(FWHM)为62nm。
实施例19
测量19的膜发射(在PMMA中为10%)。发射最大值在435nm。光致发光量子产率(PLQY)为45%。半峰全宽(FWHM)为58nm。
实施例20
测量20的膜发射。发射最大值在425nm。光致发光量子产率(PLQY)为31%。半峰全宽(FWHM)为63nm。
实施例21
测量21的膜发射(在PMMA中为10%)。发射最大值在475nm。光致发光量子产率(PLQY)为39%。半峰全宽(FWHM)为92nm。
实施例22
测量22的膜发射(在PMMA中为10%)。发射最大值在459nm。光致发光量子产率(PLQY)为54%。半峰全宽(FWHM)为74nm。
实施例23
测量23的膜发射(在PMMA中为10%)。发射最大值在432nm。光致发光量子产率(PLQY)为40%。半峰全宽(FWHM)为61nm。
实施例24
测量24的膜发射(在PMMA中为10%)。发射最大值在437nm。光致发光量子产率(PLQY)为52%。半峰全宽(FWHM)为61nm。
实施例25
测量25的膜发射(在PMMA中为10%)。发射最大值在449nm。光致发光量子产率(PLQY)为25%。半峰全宽(FWHM)为81nm。
实施例26
测量26的膜发射(在PMMA中为10%)。发射最大值在420nm。光致发光量子产率(PLQY)为22%。半峰全宽(FWHM)为61nm。
实施例27
测量27的膜发射(在PMMA中为10%)。发射最大值在435nm。光致发光量子产率(PLQY)为55%。半峰全宽(FWHM)为58nm。
实施例28
测量28的膜发射(在PMMA中为10%)。发射最大值在423nm。光致发光量子产率(PLQY)为20%。半峰全宽(FWHM)为71nm。
实施例29
测量29的膜发射(在PMMA中为10%)。发射最大值在429nm。光致发光量子产率(PLQY)为42%。半峰全宽(FWHM)为73nm。
实施例30
测量30的膜发射(在PMMA中为10%)。发射最大值在435nm。光致发光量子产率(PLQY)为41%。半峰全宽(FWHM)为77nm。
实施例31
测量31的膜发射(在PMMA中为10%)。发射最大值在405nm。光致发光量子产率(PLQY)为33%。半峰全宽(FWHM)为52nm。
实施例32
测量32的膜发射(在PMMA中为10%)(图8)。发射最大值在444nm。光致发光量子产率(PLQY)为68%。半峰全宽(FWHM)为59nm。
在具有以下构造的OLED组件(“组件X3”)中试验分子5(发射层中本发明的分子的分数以质量百分比报道):
具有根据本发明的结构的有机分子的其它实例:
附图说明
图1:1的膜发射(在PMMA中为10%)。
图2:2的膜发射(在PMMA中为10%)。
图3:3的膜发射(在PMMA中为10%)。
图4:4的膜发射(在PMMA中为10%)。
图5:5的膜发射(在PMMA中为10%)。
图6:6的膜发射(在PMMA中为10%)。
图7:7的膜发射(在PMMA中为10%)。
图8:32的膜发射(在PMMA中为10%)。
图9:9的膜发射(在PMMA中为10%)。
图10:10的膜发射(在PMMA中为10%)。
图11:11的膜发射(在PMMA中为10%)。
图12:OLED组件X3的电流密度和亮度。
图13:OLED组件X3的功率效率。
图14:OLED组件X3的电流效率。
图15:OLED组件X3的外部量子效率。
图16:在14V下操作的OLED组件X3的电致发光光谱。
Claims (16)
1.一种有机分子,其精确具有通过单键或桥基Y相互连接的两个式I的单元,
其中
Y=二价化学基团;
X=CN;
D=具有式I-1结构的化学单元:
其中
#=式I-1的单元与式I的结构的附着点;
A和B=彼此独立地选自由CRR1、CR、NR、N组成的组,在A和B之间存在单键或双键以及在B和Z之间存在单键或双键;
Z=直接的键或二价有机桥基,所述二价有机桥基为取代或未取代的C1-C9-亚烷基、C2-C8-亚烯基、C2-C8-亚炔基或亚芳基或其组合,-CRR1、-C=CRR1、-C=NR、-NR-、-O-、-SiRR1-、-S-、-S(O)-、-S(O)2-,O-间隔的取代或未取代的C1-C9-亚烷基、C2-C8-亚烯基、C2-C8-亚炔基或亚芳基、苯基单元或取代的苯基单元;
其中每个R和R1在每次出现时相同或不同地为H、氘、叠氮化物(N3 -)、F、Cl、Br、I、N(R2)2、CN、CF3、NO2、OH、COOH、COOR2、CO(NR2)2、Si(R2)3、B(OR2)2、C(=O)R2、P(=O)(R2)2、S(=O)R2、S(=O)2R2、OSO2R2,具有1至40个C原子的直链烷基、烷氧基或硫代烷氧基,或具有2至40个C原子的直链烯基或炔基,或具有3至40个C原子的支链或环状烷基、烯基、炔基、烷氧基或硫代烷氧基,在各情况下可以被一个或多个基团R2取代,一个或多个不相邻的CH2基团可以被R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S或CONR2代替,并且一个或多个H原子可以被氘、F、Cl、Br、I、CN、CF3或NO2代替,或者是具有5至60个芳族环原子的芳族或杂芳族环体系,此环体系可以在各情况下被一个或多个基团R2取代,或者是具有5至60个芳族环原子的芳氧基或杂芳氧基,此基团可以被一个或多个基团R2取代,或者是具有10至40个芳族环原子的二芳基氨基、二杂芳基氨基或芳基杂芳基氨基,此基团可以被一个或多个基团R2取代,或者是这些体系的组合,或是可交联单元QE,其可以在存在或不存在光引发剂的情况下通过酸催化、热或UV交联方法或者通过微波辐射而交联;任选地这些取代基R和R1中的两个或更多个可以彼此形成单环或多环、脂族、芳族和/或苯并稠合的环体系;
R2,在每次出现时相同或不同地为H、氘、F、Cl、Br、I、N(R3)2、CN、CF3、NO2、OH、COOH、COOR3、CO(NR3)2、Si(R3)3、B(OR3)2、C(=O)R3、P(=O)(R3)2、S(=O)R3、S(=O)2R3、OSO2R3,具有1至40个C原子的直链烷基、烷氧基或硫代烷氧基,或具有2至40个C原子的直链烯基或炔基,或具有3至40个C原子的支链或环状烷基、烯基、炔基、烷氧基或硫代烷氧基,在各情况下可以被一个或多个基团R3取代,一个或多个不相邻的CH2基团可以被R3C=CR3、C≡C、Si(R3)2、Ge(R3)2、Sn(R3)2、C=O、C=S、C=Se、C=NR3、P(=O)(R3)、SO、SO2、NR3、O、S或CONR3代替,并且一个或多个H原子可以被氘、F、Cl、Br、I、CN、CF3或NO2代替,或者是具有5至60个芳族环原子的芳族或杂芳族环体系,此体系可以在各情况下被一个或多个基团R3取代,或者是具有5至60个芳族环原子的芳氧基或杂芳氧基,此基团可以被一个或多个基团R3取代,或者是具有10至40个芳族环原子的二芳基氨基、二杂芳基氨基或芳基杂芳基氨基,此基团可以被一个或多个基团R3取代,或者是这些体系的组合;其中任选地这些取代基R2中的两个或更多个可以彼此形成单环或多环、脂族、芳族和/或苯并稠合的环体系;
R3,在每次出现时相同或不同地为H、氘、F、CF3或具有1至20个C原子的脂族、芳族和/或杂芳族烃基团,其中一个或多个H原子也可以被F或CF3代替;其中任选地两个或更多个取代基R3可以彼此形成单环或多环、脂族环体系;
R'=第二个式I的单元的附着位置或选自由以下组成的组:Y、H、N(R4)2、OR4、具有1至40个C原子的直链烷基或烷氧基或具有3至40个C原子的支链或环状烷基或烷氧基,此基团在各情况下可以被一个或多个基团R4取代,和具有5至60个芳族环原子的芳族或杂芳族环体系,此体系在各情况可下被一个或多个基团R4取代;
R”=第二个式I的单元的附着位置或选自由以下组成的组:Y、N(R4)2、OR4、具有1至40个C原子的直链烷基或烷氧基或具有3至40个C原子的支链或环状烷基或烷氧基,此基团在各情况下可以被一个或多个基团R4取代,和具有5至60个芳族环原子的芳族或杂芳族环体系,此体系在各情况下可被一个或多个基团R4取代;
其中R’和R”中所述杂芳族环体系不是N-杂芳族;
条件是如果R'为Y,则R”不为Y,并且如果R”为Y,则R'不为Y;
并且条件是如果R'是第二个式I的单元的附着位置,则R”不是第二个式I的单元的附着位置,并且如果R”是第二个式I的单元的附着位置,则R'不是第二个式I的单元的附着位置;
R4,在每次出现时相同或不同地为H、氘、N(R5)2、Si(R5)3、具有1至40个C原子的直链烷基、烷氧基或硫代烷氧基,或具有3至40个C原子的支链或环状烷基、烷氧基或硫代烷氧基,此基团在各情况下可以被一个或多个基团R5取代,或者是具有5至60个芳族环原子的芳族或杂芳族环体系,此体系在各情况下可以被一个或多个基团R5取代,或者是具有5至60个芳族环原子的芳氧基或杂芳氧基,此基团可以被一个或多个基团R5取代,或者是具有10至40个芳族环原子的二芳基氨基、二杂芳基氨基或芳基杂芳基氨基,此基团可以被一个或多个基团R5取代,或者是这些体系的组合;其中任选地这些取代基R5中的两个或更多个可以彼此形成单环或多环、脂族、芳族和/或苯并稠合的环体系;
R5,在每次出现时相同或不同地为H、氘或具有1至20个C原子的脂族、芳族和/或杂芳族烃基;其中任选地两个或更多个取代基R5还可以彼此形成单环或多环脂族环体系。
2.根据权利要求1所述的有机分子,其中
R'=第二个式I的单元的附着位置或选自由以下组成的组:Y、H、N(R4)2、OR4、可被一个或多个基团R4取代的噻吩、具有1至40个C原子的直链烷基或烷氧基,或具有3至40个C原子的支链或环状烷基或烷氧基,此基团在各情况下可以被一个或多个基团R4取代,和具有5至60个芳族环原子的芳族环体系,此体系可以被一个或多个基团R4取代;
和R”=第二个式I的单元的附着位置或选自由以下组成的组:Y、N(R4)2、OR4、可被一个或多个基团R4取代的噻吩、具有1至40个C原子的直链烷基或烷氧基,或具有3至40个C原子的支链或环状烷基或烷氧基,此基团在各情况下可以被一个或多个基团R4取代,和具有5至60个芳族环原子的芳族环体系,此体系可以被一个或多个基团R4取代;
其中,如果R'为Y,则R”不为Y,并且如果R”为Y,则R'不为Y;
并且其中,如果R'是第二个式I的单元的附着位置,则R”不是第二个式I的单元的附着位置,并且如果R”是第二个式I的单元的附着位置,则R'不是第二个式I的单元的附着位置;
其中Y和R4如权利要求1所定义。
3.根据权利要求1所述的有机分子,其中
R'为H,并且R”为第二个式I的单元的附着点或为Y;
其中Y如权利要求1所定义。
7.根据权利要求6所述的有机分子,其中R'为H。
10.根据权利要求1至8任一项所述的有机分子在有机光电器件中作为发光发射体或作为吸收剂和/或作为主体材料和/或作为电子输送材料和/或作为空穴注射材料和/或作为空穴阻挡材料的用途。
11.根据权利要求10所述的用途,其中所述有机光电器件选自由以下组成的组:
·发光电化学电池,
·OLED传感器
·有机二极管,
·有机太阳能电池,
·有机晶体管,
·有机激光器和
·下变频元件。
12.根据权利要求10或11所述的用途,其中在有机光电器件中,所述有机分子在发射层中的分数为1%至99%。
13.一种包括根据权利要求1至8任一项所述的有机分子的有机光电器件,其为选自由以下组成的组的器件的形式:发光电化学电池、OLED传感器、有机二极管、有机太阳能电池、有机晶体管、有机激光器和下变频元件。
14.根据权利要求13所述的有机光电器件,其包括
-基材,
-阳极和
-阴极,将所述阳极或所述阴极施加到所述基材上,和
-至少一个发光层,其设置在阳极和阴极之间,并且包括根据权利要求1至8任一项所述的有机分子。
15.一种生产光电组件的方法,其使用根据权利要求1至8任一项所述的有机分子。
16.根据权利要求15所述的方法,其包括通过真空蒸发工艺或从溶液中加工所述有机分子。
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