CN107848969A - 用于有机电子器件中的被至少两个电子受体和至少两个电子供体取代的苯基衍生物 - Google Patents
用于有机电子器件中的被至少两个电子受体和至少两个电子供体取代的苯基衍生物 Download PDFInfo
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- CN107848969A CN107848969A CN201680040791.8A CN201680040791A CN107848969A CN 107848969 A CN107848969 A CN 107848969A CN 201680040791 A CN201680040791 A CN 201680040791A CN 107848969 A CN107848969 A CN 107848969A
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- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- YTZKOQUCBOVLHL-UHFFFAOYSA-N p-methylisopropylbenzene Natural products CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 150000003967 siloles Chemical class 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
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Abstract
本发明涉及被至少两个电子受体和至少两个电子供体取代的苯基衍生物化合物。式(I)RA aRD bRS cC6,其中a是2、3或4;b是2、3或4;c是0、1或2;a+b+c=6;RA在每次出现时独立地是具有‑M效应的基团;RB在每次出现时独立地是具有+M效应的基团;RS如权利要求1中所限定的。所述化合物适合用于有机电子器件中,特别是有机电致发光器件中。
Description
技术领域
本发明涉及被至少两个电子受体和至少两个电子供体取代的苯基衍生物化合物。所述化合物适合用于有机电子器件中,特别是有机电致发光器件中。
背景技术
有机电子器件,即包含主要由有机材料制成的层的电子器件,与基于无机材料的常规电子器件相比,具有许多优点。有机电子器件使得能够实现例如良好的可加工性以及改进的最终性能如柔性和/或减轻的重量。通常,这些器件的特征还在于非常低的能量消耗。像这样的性能例如对于诸如平板电脑和智能电话的手持设备相当重要。
有机电子器件的具体实例是有机电致发光器件(OLED)。术语“有机电致发光器件”通常用于包含至少一种当施加电流时发光的有机材料的电子器件。通常的OLED以及它们的结构例如在US 4539507、US 5151629、EP 0676461和WO 98/27136中公开。
虽然已经取得了进展,但对改进有机电子器件、特别是有机电致发光器件例如在寿命、效率和工作电压方面的性能仍然有相当大的兴趣。在这方面的重要因素是有机发光层,特别是其中包含的材料,以及有机电荷传输层。
因此,本发明的一个目的是找到具有改进性能的新型材料。另外,本发明的一个目的是进一步增大适用于通常的有机电子器件,特别是有机电致发光器件的可用材料库。此外,本发明的一个特定目的是增大发射蓝色光的材料库。将从以下描述以及从实施例清楚本发明的其它目的。
发明内容
本申请的发明人此时已经惊奇地发现,上述目的可通过本发明化合物以及通过本申请的其它方面单独地或以任何组合的方式实现。
因此,本申请提供一种通式(I)化合物
RA aRD bRS cC6 (I)
其中
a是2、3或4;b是2、3或4;c是0、1或2;a+b+c=6;
RA在每次出现时独立地是具有-M效应的基团;
RD在每次出现时独立地是具有+-M效应的基团;
RS在每次出现时独立地选自H,D,F,Cl,Br,I,B(OR2)2,CHO,C(=O)R2,CR2=C(R2)2,CN,C(=O)OR2,C(=O)N(R2)2,Si(R2)3,N(R2)2,NO2,P(=O)(R2)2,OSO2R2,OR2,S(=O)R2,S(=O)2R2,OH,SH,具有1至20个C原子的直链的烷基、烷氧基或硫代烷基基团,或具有3至20个C原子的支链或环状的烷基、烷氧基或硫代烷基基团,或具有2至20个C原子的烯基或炔基基团,其中这些基团可被一个或多个基团R2取代,并且其中这些基团中的一个或多个CH2基团可被-R2C=CR2-、-C≡C-、Si(R2)2、C=O、C=S、C=NR2、-C(=O)O-、-C(=O)NR2-、NR2、P(=O)(R2)、-O-、-S-、SO或SO2代替,并且其中这些基团中的一个或多个H原子可被D、F、Cl、Br、I、CN或NO2代替,或具有5至60个芳族环原子的芳族或杂芳族环系,所述环系可被一个或多个基团R2取代,或具有5至60个芳族环原子的芳氧基或杂芳氧基基团,所述基团可被一个或多个基团R2取代,或具有5至60个芳族环原子的芳烷基或杂芳烷基基团,所述基团可被一个或多个基团R2取代,其中两个或更多个基团R2可彼此连接并形成脂族或芳族或杂芳族的环;
R2在每次出现时独立地选自H,D,F,具有1至20个C原子的脂族、芳族和/或杂芳族的烃基基团,其中一个或多个氢原子可被F代替,其中两个或更多个基团R2可一起形成单环或多环的脂族环系。
条件是,对于
(i)a=2,b=4且c=0;或
(ii)a=b=c=2并且两个基团RS彼此呈对位,两个基团RA彼此呈邻位并且两个基团RD彼此呈邻位,
RA不是-CN并且RD不是咔唑或被取代的咔唑。
本申请还提供一种制剂,其包含溶剂和所述化合物。
此外,本申请提供一种制造电子器件的方法,所述方法包括以下步骤:
(a)提供所述化合物或包含所述化合物的低聚物、聚合物或树枝状大分子;和
(b)将所述化合物或所述低聚物、聚合物或树枝状大分子沉积在支撑层上。
另外,本申请提供包含所述化合物的有机电子器件,特别是有机电致发光器件。
具体实施方式
定义
出于本申请的目的,术语“有机发光器件”和“有机电致发光器件”可互换使用。
出于本申请的目的,术语“基团”和“取代基”同义使用。
出于本申请的目的,术语“取代的”意在表示如本申请中所限定的取代基R2。
在本申请的化学式中,可使用双键来表示芳族或杂芳族环系中的芳族键。
在本申请中表示为“M效应”的中介(mesomeric)效应归因于取代基或基团,因为其p或π轨道与分子实体的其余部分的p或π轨道重叠而导致该效应。由此引入或扩展了离域,并且电子电荷可流向取代基或从该取代基流出。参见International Union of Pure andApplied Chemistry(国际纯粹与应用化学联合会),Compendium of Chemical Technology(化学技术概要),Gold Book(金色书),2.3.2版,2012-08-19。具有+M效应(“正M效应”)的基团将电子密度贡献给中介体系。具有-M效应(“负M效应”)的基团接受来自中介体系的电子密度。
在本申请中,R1在每次出现时独立地选自H,D,F,Cl,Br,I,B(OR2)2,CHO,C(=O)R2,CR2=C(R2)2,CN,C(=O)OR2,C(=O)N(R2)2,Si(R2)3,N(R2)2,NO2,P(=O)(R2)2,OSO2R2,OR2,S(=O)R2,S(=O)2R2,OH,SH,具有1至20个C原子的直链的烷基、烷氧基或硫代烷基基团,或具有3至20个C原子的支链或环状的烷基、烷氧基或硫代烷基基团,或具有2至20个C原子的烯基或炔基基团,其中这些基团可被一个或多个基团R2取代,并且其中这些基团中的一个或多个CH2基团可被-R2C=CR2-、-C≡C-、Si(R2)2、C=O、C=S、C=NR2、-C(=O)O-、-C(=O)NR2-、NR2、P(=O)(R2)、-O-、-S-、SO或SO2代替,并且其中这些基团中的一个或多个H原子可被D、F、Cl、Br、I、CN或NO2代替,或具有5至60个芳族环原子的芳族或杂芳族环系,所述环系可被一个或多个基团R2取代,或具有5至60个芳族环原子的芳氧基或杂芳氧基基团,所述基团可被一个或多个基团R2取代,或具有5至60个芳族环原子的芳烷基或杂芳烷基基团,所述基团可被一个或多个基团R2取代,其中两个或更多个基团R2可彼此连接并形成脂族或芳族或杂芳族的环。
在本申请中,R2在每次出现时独立地选自H,D,F,具有1至20个C原子的烷基,具有1至20个芳族碳原子的芳族基团和具有1至20个芳族环原子的杂芳族基团,其中所述芳族基团和杂芳族基团可被具有1至20个碳原子的烷基取代。对于R2,优选的示例性的具有1至20个C原子的烷基可选自甲基、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、环戊基、新戊基、正己基、环己基、新己基、正庚基、环庚基、正辛基、环辛基和2-乙基己基。对于R2,优选的示例性的具有1至20个芳族碳原子的芳族基团和具有1至20个芳族环原子的杂芳族基团可选自苯、萘、蒽、苯并蒽、菲、苯并菲、芘、苝、荧蒽、并四苯、并五苯、苯并芘、联苯、偶苯、三联苯、三聚苯、四联苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式或反式茚并芴、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、吲哚并咔唑、茚并咔唑、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、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、蝶啶、吲嗪、苯并噻二唑以及其烷基取代衍生物,其中所述烷基具有1至20个C原子。
在本申请中,R3在每次出现时独立地选自F,具有1至20个C原子的直链的烷基或烷氧基基团,具有3至20个C原子的支链或环状的烷基或烷氧基基团,所述基团中的每个可被一个或多个基团R2取代,其中一个或多个非相邻的CH2基团可被R2C=CR2、C≡C、Si(R2)2、C=O、NR2、O、S或CONR2代替,并且其中一个或多个H原子可被D或F代替,或具有5至24个芳族环原子的芳族或杂芳族环系,所述环系中的每个可各自被一个或多个基团R2取代,或具有5至24个芳族环原子的芳氧基或杂芳氧基基团,所述基团可被一个或多个基团R2取代,或具有5至24个芳族环原子的芳烷基或杂芳烷基基团,所述基团可被一个或多个基团R2取代,其中键合至同一碳原子的两个R2可形成脂族或芳族的环系并因此形成螺环系;或者R3可与相邻的基团R1或R2一起形成脂族环系。
出于本发明的目的,直链、支链或环状的烷基、烯基和炔基基团可优选选自甲基、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、环戊基、新戊基、正己基、环己基、新己基、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、辛炔基和相应取代衍生物,其中它们可被一个或多个基团R2取代,并且其中这些基团中的一个或多个CH2基团可被-R2C=CR2-、-C≡C-、Si(R2)2、C=O、C=S、C=NR2、-C(=O)O-、-C(=O)NR2-、NR2、P(=O)(R2)、-O-、-S-、SO或SO2代替,并且其中这些基团中的一个或多个H原子可被D、F、Cl、Br、I、CN或NO2代替。
出于本发明的目的,直链或支链的烷氧基和硫代烷基、烯基和炔基基团可优选选自甲氧基、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、2,2,2-三氟乙氧基、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、辛炔硫基和相应取代衍生物,其中它们可被一个或多个基团R2取代,并且其中这些基团中的一个或多个CH2基团可被-R2C=CR2-、-C≡C-、Si(R2)2、C=O、C=S、C=NR2、-C(=O)O-、-C(=O)NR2-、NR2、P(=O)(R2)、-O-、-S-、SO或SO2代替,并且其中这些基团中的一个或多个H原子可被D、F、Cl、Br、I、CN或NO2代替。
出于本发明的目的,芳族环系优选具有6至60个芳族环原子,最优选6至30个芳族环原子。出于本发明的目的,杂芳族环系优选具有5至60个芳族环原子,最优选5至30个芳族环原子,所述环原子中的至少一个是杂原子。合适的杂原子可选自N、O和S。如本文所用的术语“芳族环系”和“杂芳族环系”也可表示其中多个芳基或杂芳基基团通过非芳族单元连接的体系。优选地,这样的非芳族单元包含芳族或杂芳族环系中所包含的不同于H和D的原子的至多10%。合适的非芳族单元的实例可选自sp3杂化的原子(其中所述原子选自C、Si、N和O),sp2杂化的C原子,sp2杂化的N原子和sp杂化的C原子。出于本申请的目的,例如9,9'-螺二芴、9,9'-二芳基芴、三芳基胺、二芳基醚、二苯乙烯的体系,以及其中两个或更多个芳基基团例如通过甲硅烷基的直链或环状的烷基、烯基或炔基基团连接的体系,被认为是芳族环系。此外,出于本申请的目的,其中一个或多个芳基或杂芳基基团通过一个或多个单键连接的体系,例如联苯、三联苯或二苯基三嗪,被认为是芳族或杂芳族体系。
可任选地如上文所限定地被取代并且任选地在如本申请中所限定的芳族或杂芳族环上的任何位置处连接的合适的芳族或杂芳族环系的实例优选选自苯、萘、蒽、苯并蒽、菲、苯并菲、芘、苝、荧蒽、并四苯、并五苯、苯并芘、联苯、偶苯、三联苯、三聚苯、四联苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式或反式茚并芴、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、吲哚并咔唑、茚并咔唑、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、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、蝶啶、吲嗪、苯并噻二唑和任何组合以及其衍生物。
芳基和杂芳基基团(所述基团任选地如上文所限定地被取代并且任选地在如本申请中所限定的芳族或杂芳族环上的任何位置处连接)的实例优选选自苯、萘、蒽、菲、芘、二氢芘、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、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、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、蝶啶、吲嗪和苯并噻二唑。
出于本申请的目的,术语“芳氧基基团”和“杂芳氧基基团”分别用于表示经由二价(醚型)O原子共价键合的如上文所定义的芳基和杂芳基基团。
出于本申请的目的,术语“芳烷基基团”和“杂芳烷基基团”分别用于表示如下芳基和杂芳基基团,其中所述芳基或杂芳基基团被具有1至20个C原子的烷基基团取代,其中在所述烷基基团中,任何H或D原子或任何CH2基团可被上述基团取代,并且其中所述烷基基团用于将芳基或杂芳基基团键合到化合物的其余部分。
化合物
一般而言,本发明化合物的特征在于苯基衍生的结构,其如本文所定义被至少两个电子供体基团和至少两个电子受体基团取代。
H.Uoyama等,Nature(自然),第492卷,2012年12月13日,第234-238页最近公开了类似的化合物。
本发明化合物可由通式(I)表示
RA aRD bRS cC6 (I)
其中RA、RD、RS、a、b和c如本文所限定。
参数a是2、3或4。参数b是2、3或4。参数c是0、1或2。参数a、b和c彼此独立地选择,条件是a+b+c=6。
基团RA彼此独立地选自具有-M效应的基团。所述基团通常是本领域普通技术人员所熟知的并且可见于许多常见的有机化学教科书中。
基团RA的优选实例可选自氟烷基,F,BR1 2,B(OR1)2,CHO,C(=O)R1,CN,C(=O)OR1,C(=O)N(R1)2,CR1=C(CN)2,N3,NO2,P(=O)(R1)2,S(=O)R1,S(=O)2R1,杂芳基,被一个或多个吸电子基团取代的杂芳基和被一个或多个吸电子基团取代的芳基,其中所述吸电子基团选自氟烷基、F、B(OR1)2、CHO、C(=O)R1、CN、C(=O)OR1、C(=O)N(R1)2、NO2、P(=O)(R1)2、S(=O)R1和S(=O)2R1,其中R1如上文所限定。
更优选地,RA在每次出现时独立地选自氟烷基,F,C(=O)R1,CN,杂芳基,被一个或多个吸电子基团取代的杂芳基和被一个或多个吸电子基团取代的芳基,其中所述吸电子基团选自氟烷基、F、C(=O)R1和CN,其中R1如上文所限定。
甚至更优选地,RA在每次出现时独立地选自氟烷基,F,CN,杂芳基,被一个或多个吸电子基团取代的杂芳基和被一个或多个吸电子基团取代的芳基,其中所述吸电子基团选自氟烷基、F、CN。
甚至更优选地,RA在每次出现时独立地选自F和CN。
最优选地,RA是CN。
基团RD彼此独立地选自具有+M效应的基团。所述基团通常是本领域普通技术人员所熟知的并且可见于许多常见的有机化学教科书中。
基团RD的优选实例可具有通式(II)
其中Ar1、Ar2和Y如本文所限定。
Ar1和Ar2彼此独立地选自未被取代的具有6至60个芳族环原子的芳族环系,被取代的具有6至60个芳族环原子的芳族环系,未被取代的具有5至60个芳族环原子的杂芳族环系和被取代的具有6至60个芳族环原子的杂芳族环系。
合适的连接基团Y可例如选自单键、BR1、C(R1)2、Si(R1)2、NR1、PR1、P(=O)R1、P(=S)R1、O、S、S=O和S(=O)2,其中R1如上文所限定。
优选地,所述连接基团Y可选自单键、BR1、C(R1)2、Si(R1)2、NR1、P(=O)R1、O、S和S(=O)2,其中R1如上文所限定。
更优选地,所述连接基团Y可选自单键、BR1、C(R1)2、NR1、P(=O)R1、O和S(=O)2,其中R1如上文所限定。
甚至更优选地,所述连接基团Y可选自单键、C(R1)2、NR1和O,或者可选地选自单键、NR1和O,其中R1如上文所限定。
甚至更优选地,所述连接基团Y可选自单键和O。
最优选地,所述连接基团Y是单键。
特别合适的是如下的式(II)基团,其选自咔唑、氮杂咔唑、缩合咔唑、缩合氮杂咔唑、5,10-二氢-吩硼嗪(5,10-dihydro-phenazaboranes)、9,10-二氢吖啶、9,10-二氢-10-硅杂-吖啶、9,10-二氢-吩嗪、10-氢-吩嗪和10-氢-吩噻嗪,其全部可被取代或未被取代。
咔唑和氮杂咔唑以及相应的缩合衍生物的合适实例由下式(N-1)至(N-11)示出:
5,10-二氢-吩硼嗪、9,10-二氢吖啶、9,10-二氢-10-硅杂-吖啶、9,10-二氢-吩嗪、10-氢-吩嗪和10-氢-吩噻嗪的合适实例由下式(N-12)至(N-16)示出:
在上述式(N-1)至(N-16)中
X是N或CR4,其中R4如上文对于R2所限定的;
X1是BR2、CR1 2、NR2、O或S;优选地CR1 2、NR2、O或S;最优选地CR1 2或NR2,其中R2如上文所限定的;
R5是未被取代的芳基、未被取代的杂芳基、被取代的芳基或被取代的杂芳基,其如果被取代,则优选在2位和6位处被烷基、芳基或CN取代;并且
R6是烷基、未被取代的芳基、未被取代的杂芳基、被取代的芳基或被取代的杂芳基,其任选地可通过如上文所限定的基团Y连接。
基团RS在存在时彼此独立地选自如上文关于R1所限定的群组。RS的优选合适实例可选自H、具有1至10个碳原子的烷基和其中一个或多个氢原子被氟代替的具有1至10个碳原子的烷基。
式(I)化合物的合适实例可选自下式(I-A-1)和(I-A-2)
其中a、b、c、RA、RD和RS如本文所限定。
本发明的式(I)化合物关于参数a、b和c可具有以下组成:
a | b | c | |
(K-1) | 4 | 2 | 0 |
(K-2) | 3 | 3 | 0 |
(K-3) | 3 | 2 | 1 |
(K-4) | 2 | 4 | 0 |
(K-5) | 2 | 3 | 1 |
(K-6) | 2 | 2 | 2 |
其中a=4、b=2和c=0的实例可选自下式(I-B-1)至(I-B-3):
其中a=3、b=3和c=0的实例可选自下式(I-B-4)至(I-B-6):
其中a=3、b=2和c=1的实例可选自下式(I-B-7)至(I-B-12):
其中a=2、b=4和c=0的实例可选自下式(I-B-13)至(I-B-15):
其中a=2、b=3和c=1的实例可选自下式(I-B-16)至(I-B-21):
其中a=2、b=2和c=2的实例可选自下式(I-B-22)至(I-B-32):
式(II)化合物的特别合适的实例是选自式(I-B-1)至(I-B-12)、(I-B-16)至(I-B-24)和(I-B-26)至(I-B-32)的那些,其中RA是-CN并且RD是咔唑或被取代的咔唑。
对于本发明的通式(I)化合物,RA、RD、RS、a、b和c可如本文中所限定地进行选择,条件是,对于
(i)a=2,b=4且c=0;或
(ii)a=b=c=2并且两个基团RS彼此呈对位,两个基团RA彼此呈邻位并且两个基团RD彼此呈邻位,
RA不是-CN并且RD不是咔唑或被取代的咔唑。换言之,对于RA是-CN并且RD是咔唑或被取代的咔唑,本发明化合物不能是式(I-B-13)、(I-B-14)、(I-B-15)和(I-B-25)中的任何一种。
低聚物、聚合物、树枝状大分子
通式(I)化合物,特别是包含反应性基团的这些化合物,可用作单体来制造相应的低聚物、聚合物或树枝状大分子。因此,本发明还提供包含所述通式(I)化合物的低聚物、聚合物和树枝状大分子。
示例性的反应性基团可彼此独立地(如果存在多于一个的这种基团)选自Cl,Br,I,硼酸,硼酸酯,胺,具有末端碳碳双键的烯基,具有末端碳碳三键的炔基,环氧乙烷,氧杂环丁烷,能够进行环加成、特别是1,3-偶极环加成的基团(例如二烯或叠氮化物),碳酸、醇和硅烷的衍生物。这些反应性基团可包含在通式(I)化合物中,例如在基团RA、RD和RS中和/或直接在环碳原子上,如在例如基团Q1、Q2、Z1和Z2的任一个或多个中。取决于式(I)化合物中的一个或多个反应性基团的位置,化合物(I)可最终位于低聚物、聚合物或树枝状大分子的主链中和/或侧链中。
出于本申请的目的,低聚物应理解为包含至少3个重复单元,并且聚合物应理解为包含至少10个重复单元,所述重复单元包含至少一种通式(I)化合物。应注意,上文关于式(I)化合物的定义也适用于这里。
本发明的低聚物、聚合物和树枝状大分子可以是共轭、部分共轭或不共轭的。它们也可以是直链、支链或树枝状的。在直链结构中,重复单元可由合适的式(I)化合物组成,或者可通过二价基团例如被取代或未被取代的亚烷基基团、杂原子或二价芳族或杂芳族基团连接。在支链或树枝状结构中,三个或甚至更多个合适的通式(I)化合物可通过三价或甚至更高价的基团(例如通过三价或更高价的芳族或杂芳族基团)连接,以形成支链或树枝状的低聚物或聚合物。
本发明的低聚物或聚合物可均聚或在至少一种其它单体(在下文中称为“共聚单体”)的存在下共聚。合适的共聚单体可选自芴(例如在EP 842208或WO 00/22026中公开的那些),螺二芴(例如在EP 707020、EP 894107或WO 06/061181中公开的那些),对亚苯基(例如在WO 1992/18552中公开的那些),咔唑(例如在WO 04/070772或WO 2004/113468中公开的那些),噻吩(例如在EP 1028136中公开的那些),二氢菲(例如在WO 2005/014689或WO2007/006383中公开的那些),顺式和反式茚并芴(例如在WO 2004/041901或WO 2004/113412中公开的那些),酮(例如在WO 2005/040302中公开的那些),菲(例如在WO 2005/104264或WO 2007/017066中公开的那些)以及这些中的任何一种或多种的共混物。
本发明的低聚物、聚合物和树枝状大分子可包含其它组分,例如发光化合物,其中乙烯基三芳基胺(例如在WO 2007/068325中公开的那些)或金属络合物(例如在WO 2006/003000中公开的那些),和/或电荷传输组分,特别是包含三芳基胺的那些。
本发明的低聚物、聚合物和树枝状大分子通常可通过众所周知的聚合方法来制备。作为导致形成C-C或C-N键的特别合适的聚合方法,可提及以下方法:
(A)SUZUKI聚合;
(B)YAMAMOTO聚合;
(C)STILLE聚合;和
(D)HARTWIG-BUCHWALD聚合。
包括相应聚合条件的这些方法是本领域普通技术人员众所周知的,并且也在文献中详细描述,例如在WO 2003/048225、WO 2004/037887和WO 2004/037887中详细描述。
因此,本申请还提供了通过根据选自Suzuki聚合、Yamamoto聚合、Stille聚合和Hartwig-Buchwald聚合的方法进行聚合来制备上述低聚物和聚合物的方法。相应的树枝状大分子可根据这些方法或类似的方法制备。适于制备这些树枝状大分子的方法例如公开于Jean M.J.Frechet,Craig J.Hawker,"Hyperbranched polyphenylene andhyperbranched polyesters:new soluble,three-dimensional,reactive polymers(超支化聚亚苯基和超支化聚酯:新的可溶性三维反应性聚合物)",Reactive&FunctionalPolymers(活性和功能聚合物)(1995),26(1-3),127-36;H.M.Janssen,E.W.Meijer,"Thesynthesis and characterization of dendritic molecules(树枝状分子的合成和表征)",Materials Science and Technology(材料科学与技术)(1999),20(Synthesis ofPolymers(聚合物的合成)),403-458;Donald A.Tomalia,"Dendrimer molecules(树枝状分子)",Scientific American(科学美国人)(1995),272(5),62-6;WO 2002/067343 A1;以及WO 2005/026144 A1中。
根据本发明的化合物和聚合物还可以以混合物或聚合物共混物的形式使用,例如与单体化合物一起或与具有电荷传输、半导体、导电、光电导和/或发光半导体特性的其它聚合物一起,或者例如与具有空穴阻挡或电子阻挡特性的聚合物一起,用作OLED器件中的中间层或电荷阻挡层。因此,本发明的另一方面涉及一种聚合物共混物,其包含一种或多种根据本发明的聚合物和一种或多种具有一种或多种上述性质的其它聚合物。这些共混物可通过现有技术中描述的和本领域普通技术人员已知的常规方法来制备。通常,将聚合物彼此混合或溶解在合适的溶剂中并将溶液合并。
制剂
本发明的另一方面涉及一种制剂,其包含一种或多种如上文和下文所述的式(I)化合物、低聚物、聚合物、树枝状大分子或聚合物共混物以及一种或多种有机溶剂。这种制剂可以是溶液、悬浮液或乳液。这种制剂的制造是众所周知的,并且例如在WO 2002/072714、WO 2003/019694和其中引用的文献中公开。
合适的有机溶剂可例如选自甲苯,苯甲醚,邻二甲苯,间二甲苯,对二甲苯,苯甲酸甲酯,均三甲苯,萘满,1,2-二甲氧基苯(通常称为“藜芦醚”),四氢呋喃(通常缩写为“THF”),甲基-四氢呋喃,四氢吡喃(烷),氯苯,二烷,苯氧基甲苯,特别是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,萘烷,十二烷基苯,苯甲酸乙酯,茚满,N-甲基-2-吡咯烷酮(通常缩写为“NMP”),对甲基异丙基苯,乙基苯基醚,1,4-二异丙基苯、二苄醚,二乙二醇丁甲醚,三乙二醇丁甲醚,二乙二醇二丁醚,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,戊苯,己苯,庚苯,辛苯,1,1-双(3,4-二甲基-苯基)乙烷和这些中的任何物质的共混物。
有机电子器件
本发明的化合物、低聚物、聚合物和树枝状大分子可用作有机电子器件中的活性材料。术语“活性材料”在本文中用于表示例如电荷注入材料、电荷传输材料、电荷阻挡材料、发光材料或基质材料。
优选地,所述有机电子器件包含阳极、阴极和活性层,所述活性层包含所述活性材料。本发明的有机电子器件包括(但不限于)光学、电光、电子、电致发光和光致发光器件。其实例包括(但不限于)有机场效应晶体管(OFET)、有机薄膜晶体管(OTFT)、有机发光二极管(OLED)、有机发光晶体管(OLET)、有机光伏器件(OPV)、有机光学检测器(OPD)、有机太阳能电池、激光二极管、肖特基二极管、光电导体和光电二极管。优选地,本发明的器件选自有机发光二极管和有机发光晶体管。最优选地,本发明的器件是有机发光二极管。
除了阳极、阴极和活性层之外,本发明的有机电子器件还可任选地包含至少一个另外的层,其选自电子传输层、空穴传输层、空穴注入层、电子注入层、激子阻挡层、中间层和电荷产生层。所述另外的层的存在(或不存在)取决于有机器件的类型和相应的最终用途。
因为本发明的化合物、低聚物、聚合物或树枝状大分子在有机电致发光器件中作为发光材料使用时显示出特别有利的性能,所以优选将它们用作这些器件的发光层中的发光材料。
如果本发明的有机电子器件是有机电致发光器件,则其包含阳极、阴极和发光层。任选地,除了这些之外,它还可包含一个或多个另外的层,其选自空穴注入层、空穴传输层、空穴阻挡层、电子注入层、电子传输层、电子阻挡层、电荷产生层、激子阻挡层、有机p/n过渡层和无机p/n过渡层。一个或多个空穴传输层也可包含p型掺杂剂。示例性的p型掺杂剂是金属氧化物和(全)氟化的缺电子芳族化合物。合适的金属氧化物的实例是(但不限于)MoO3和WO3。此外可行的是,与空穴传输层的任何掺杂无关,一个或多个电子传输层被n型掺杂剂掺杂。任选地,中间层如果存在,则可存在于两个发光层之间,其例如具有激子阻挡功能和/或引导有机电致发光器件中的电荷平衡。
本发明的有机电子器件也可能具有多于一个的发光层。在这种情况下,优选不同的发光层具有介于380nm与750nm之间的不同的发光峰值,从而使得发射不同颜色的光,并且例如导致发射白光。在这方面尤其优选的是包含三个发光层的有机电子器件,其中优选其中至少一个包含本申请的化合物、低聚物、聚合物或树枝状大分子,并且所述三个发光层发射蓝光、绿光和橙光或红光。关于这种器件的基本结构的描述,例如参考WO 2005/011013。应注意到,代替多种不同的发光化合物,也可使用在宽波长范围内发光并且总体发射白光的一种化合物。
在本发明的一个优选方面中,所述通式(I)化合物被用作一个或多个发光层中的发光体。
如果用作发光层中的发光体,则式(I)化合物优选与一种或多种基质材料组合使用。相对于混合物的总体积,包含式(I)化合物和基质材料的混合物优选包含0.1体积%至99体积%、优选1体积%至90体积%、甚至更优选3体积%至40体积%、最优选5体积%至15体积%的式(I)化合物。
作为基质材料,可使用本领域普通技术人员已知的任何合适的材料,优选其中基质材料的三重态能级高于发光体的三重态能级的这些材料。
本文所用的合适的基质材料可选自以下:酮,氧化膦,亚砜,砜,三芳基胺,咔唑衍生物,吲哚并咔唑衍生物,茚并咔唑衍生物,氮杂咔唑,双极性基质材料,硅烷,氮杂硼杂环戊二烯,硼酸酯,二氮杂硅杂环戊二烯衍生物,三嗪衍生物,锌络合物,二苯并呋喃衍生物和桥连咔唑衍生物。亚砜和砜的合适实例例如公开于WO 2004/013080、WO 2004/093207、WO2006/005627或WO 2010/006680中。咔唑的合适衍生物是例如CBP(N,N-双咔唑基联苯),m-CBP或在WO 2005/039246、US 2005/0069729、JP 2004/288381、EP 1205527、WO 2008/086851和US 2009/0134784中公开的那些。吲哚并咔唑的合适衍生物是例如在WO 2007/063754或WO 2008/056746中公开的那些。茚并咔唑衍生物的合适实例是例如在WO 2010/136109或WO2011/000455中公开的那些。氮杂咔唑的合适实例例如公开在EP 1617710、EP1617711、EP 1731584或JP 2005/347160中。双极性基质材料的合适实例例如公开在WO2007/137725中。硅烷的合适实例例如公开在WO 2005/111172中。氮杂硼杂环戊二烯或硼酸酯的合适实例例如公开在WO 2006/117052中。二氮杂硅杂环戊二烯的合适衍生物例如公开在WO 2010/054729中。二氮杂磷杂环戊二烯的合适衍生物例如公开在WO 2010/054730中。合适的三嗪衍生物例如公开在WO 2010/015306、WO 2007/063754或WO 2008/056746中。合适的锌络合物例如公开在EP 652273或WO 2009/062578中。二苯并呋喃的合适衍生物例如公开在WO 2009/148015中。咔唑的桥连衍生物的合适实例例如公开在US 2009/0136779、WO2010/050778、WO 2011/042107或WO 2011/088877中。
可选地,本申请的化合物、低聚物、聚合物或树枝状大分子可存在于有机电子器件中存在的任何其它层中,例如存在于电子传输层中。
优选地,层的顺序如下:
-阳极,
-任选的空穴注入层,
-任选的一个或多个空穴传输层,
-发光层,
-任选的电子传输层,
-任选的电子注入层,和
-阴极。
应注意,取决于所得器件的预期用途和/或期望性质,任何指示为“任选”的层可存在或不存在。
阳极通常由导电材料形成。示例性的导电材料包括导电金属、导电合金、导电聚合物和导电金属氧化物。示例性的导电金属包括金、银、铜、铝、镍、钯、铂和钛。示例性的导电合金包括不锈钢(例如332不锈钢、316不锈钢)、金合金、银合金、铜合金、铝合金、镍合金、钯合金、铂合金以及钛合金。示例性的导电聚合物包括聚噻吩(例如掺杂的聚(3,4-亚乙基二氧基噻吩)),聚苯胺(例如掺杂的聚苯胺),聚吡咯(例如掺杂的聚吡咯)。示例性的导电金属氧化物包括氧化铟锡、氧化铟锌、氟化氧化锡、氧化锡和氧化锌。优选的是,阳极由具有高逸出功的材料形成,例如逸出功相对于真空为至少4.5eV。在一些实施方式中,使用导电材料的共混物或组合。在一些实施方式中,形成透明材料(例如氧化铟锡或氧化铟锌)的阳极可能是有利的。可选地,阳极可包含多于一个的层,例如它可包含氧化铟锡的内层和氧化钨、氧化钼或氧化钒的外层。
阴极通常由导电材料、优选具有低逸出功的导电材料形成。合适的示例性材料是金属,例如碱土金属、主族金属或镧系元素。这些金属的特别实例是Ca、Ba、Mg、Al、In、Yb、Sm和Eu以及它们的合金。也可使用银与碱金属或碱土金属的合金,例如银与镁的合金。阴极也可由多于一个的层形成,在这种情况下,可存在具有较高逸出功的金属或合金。具有较高逸出功的这些金属或合金的实例是Ag、Al、Ca/Ag合金、Mg/Ag合金和Ba/Ag合金。
在一些实施方式中,阴极还可包含具有高介电常数的材料的层。合适材料的实例是金属氟化物、氧化物或碳酸盐,其中所述金属选自碱金属和碱土金属。这些材料的具体实例是LiF、Li2O、BaF2、MgO、NaF、CsF、Cs2CO3或CaF2。也可使用喹啉锂。
用于电荷传输层,例如用于空穴传输层或电子传输层的其它合适的材料例如在Y.Shirota等,Chemical Reviews(化学评论)2007,107(4),953-1010中公开。合适的实例是铝络合物、锆络合物、苯并咪唑、三嗪、吡啶、嘧啶、吡嗪、喹喔啉、喹啉、二唑、芳族酮、内酰胺、硼烷、二氮杂磷杂环戊二烯、氧化膦和其衍生物,如在例如JP2000/053957、WO 2003/060956、WO 2004/028217、WO 2004/080975或WO 2010/072300中所公开的。
可用于空穴传输、空穴注入或电子阻挡层中的空穴传输材料的优选实例是茚并芴胺衍生物(例如在WO 06/122630或WO 06/100896中公开的),胺(例如EP 1661888中公开的胺或WO 95/09147中公开的那些),六氮杂苯并菲衍生物(例如在WO 01/049806中公开的),具有缩合芳基的胺的衍生物(例如,如US 5,061,569中所公开的),单苯并茚并芴胺(例如,如WO 08/006449中所公开的),二苯并茚并芴胺(例如,如WO 07/140847中所公开的),螺二芴胺(例如,如WO 2012/034627中所公开的),芴胺,螺二苯并吡喃胺和吖啶衍生物。
为了避免或降低水和空气的破坏作用,随后将本发明的有机电子器件封闭和密封。
如上文所定义的本发明化合物、低聚物、聚合物或树枝状大分子,或者如上文所定义的它们各自的制剂,可用于制造有机电子器件,特别是有机发光二极管(OLED)。特别地,它们可用于制造有机发光二极管的发光层。
本发明的有机电子器件可通过任何合适的方法制造。例如,可通过升华,通过有机气相沉积(OPVD),通过载气升华,通过有机蒸气喷印,通过旋涂或通过任何印刷方法例如丝网印刷、喷墨印刷、柔性版印刷或光引发热成像,来沉积包含在这种有机电子器件中的一个或多个层。
因此,本发明还提供一种制造本发明电子器件的方法,所述方法包括以下步骤
(a)提供本发明的化合物、聚合物、低聚物或树枝状大分子;和(b)将所述化合物、聚合物、低聚物或树枝状大分子沉积在支撑层上。
本发明的有机电子器件可例如用于显示器中,照明器具中的光源以及例如医疗和美容器具中。
据信本发明的化合物、低聚物、聚合物和树枝状大分子在有机发光器件中具有特别有利的性质,因为S1能级与T1能级之间的能量差减小,这已经通过计算得到证实。不希望被理论所束缚,认为这是本发明化合物的六元环上的取代基的特定排列的结果。所述计算此外表明,本发明的化合物将在蓝光区域发光,并且因此特别适用于有机发光化合物中。
Claims (11)
1.一种通式(I)化合物,
RA aRD bRS cC6 (I)
其中
a是2、3或4;b是2、3或4;c是0、1或2;a+b+c=6;
RA在每次出现时独立地是具有-M效应的基团;
RD在每次出现时独立地是具有+-M效应的基团;
RS在每次出现时独立地选自H,D,F,Cl,Br,I,B(OR2)2,CHO,C(=O)R2,CR2=C(R2)2,CN,C(=O)OR2,C(=O)N(R2)2,Si(R2)3,N(R2)2,NO2,P(=O)(R2)2,OSO2R2,OR2,S(=O)R2,S(=O)2R2,OH,SH,具有1至20个C原子的直链的烷基、烷氧基或硫代烷基基团,或具有3至20个C原子的支链或环状的烷基、烷氧基或硫代烷基基团,或具有2至20个C原子的烯基或炔基基团,其中这些基团可被一个或多个基团R2取代,并且其中这些基团中的一个或多个CH2基团可被-R2C=CR2-、-C≡C-、Si(R2)2、C=O、C=S、C=NR2、-C(=O)O-、-C(=O)NR2-、NR2、P(=O)(R2)、-O-、-S-、SO或SO2代替,并且其中这些基团中的一个或多个H原子可被D、F、Cl、Br、I、CN或NO2代替,或具有5至60个芳族环原子的芳族或杂芳族环系,所述环系可被一个或多个基团R2取代,或具有5至60个芳族环原子的芳氧基或杂芳氧基基团,所述基团可被一个或多个基团R2取代,或具有5至60个芳族环原子的芳烷基或杂芳烷基基团,所述基团可被一个或多个基团R2取代,其中两个或更多个基团R2可彼此连接并形成脂族或芳族或杂芳族的环;
R2在每次出现时独立地选自H,D,F,具有1至20个C原子的脂族、芳族和/或杂芳族的烃基基团,其中一个或多个氢原子可被F代替,其中两个或更多个基团R2可一起形成单环或多环的脂族环系,
条件是,对于
(i)a=2,b=4且c=0;或
(ii)a=b=c=2并且两个基团RS彼此呈对位,两个基团RA彼此呈邻位并且两个基团RD彼此呈邻位,
RA不是-CN并且RD不是咔唑或被取代的咔唑。
2.根据权利要求1所述的化合物,其中所述化合物为式(I-A-1)和(I-A-2)之一
其中a、b、c、RA、RD和RS如权利要求1中所限定的。
3.根据权利要求1所述的化合物,其中所述化合物选自式(I-B-1)至(I-B-32)
其中a、b、c、RA、RD和RS如权利要求1中所限定的。
4.根据前述权利要求中的任一项或多项所述的化合物,其中RA在每次出现时独立地选自-CN、-F、-(CH2)d-CF3和-C6R5,其中d是0、1、2、3或4,其中R选自-CN、-F、-(CH2)d-CF3,其中d是0、1、2、3或4。
5.根据前述权利要求中的任一项或多项所述的化合物,其中RD在每次出现时独立地是通式(II)的基团
其中
Ar1和Ar2彼此独立地选自被取代或未被取代的具有5至30个芳族环原子的芳基或杂芳基;
Y选自单键、BR1、C(R1)2、Si(R1)2、NR1、PR1、P(=O)R1、P(=S)R1、O、S、S=O和S(=O)2;并且
R1在每次出现时独立地选自H,D,F,Cl,Br,I,B(OR2)2,CHO,C(=O)R2,CR2=C(R2)2,CN,C(=O)OR2,C(=O)N(R2)2,Si(R2)3,N(R2)2,NO2,P(=O)(R2)2,OSO2R2,OR2,S(=O)R2,S(=O)2R2,OH,SH,具有1至20个C原子的直链的烷基、烷氧基或硫代烷基基团,或具有3至20个C原子的支链或环状的烷基、烷氧基或硫代烷基基团,或具有2至20个C原子的烯基或炔基基团,其中这些基团可被一个或多个基团R2取代,并且其中这些基团中的一个或多个CH2基团可被-R2C=CR2-、-C≡C-、Si(R2)2、C=O、C=S、C=NR2、-C(=O)O-、-C(=O)NR2-、NR2、P(=O)(R2)、-O-、-S-、SO或SO2代替,并且其中这些基团中的一个或多个H原子可被D、F、Cl、Br、I、CN或NO2代替,或具有5至60个芳族环原子的芳族或杂芳族环系,所述环系可被一个或多个基团R2取代,或具有5至60个芳族环原子的芳氧基或杂芳氧基基团,所述基团可被一个或多个基团R2取代,或具有5至60个芳族环原子的芳烷基或杂芳烷基基团,所述基团可被一个或多个基团R2取代,其中两个或更多个基团R2可彼此连接并形成脂族或芳族或杂芳族的环;
R2在每次出现时独立地选自H,D,F,具有1至20个C原子的脂族、芳族和/或杂芳族的烃基基团,其中一个或多个氢原子可被F代替,其中两个或更多个基团R2可一起形成单环或多环的脂族环系。
6.一种低聚物、聚合物或树枝状大分子,所述低聚物、聚合物或树枝状大分子包含一种或多种根据前述权利要求中的任一项或多项所述的化合物,其中至少一个与所述低聚物、聚合物或树枝状大分子连接的键在基团RA、RD或RS的任一个或多个上。
7.一种制剂,所述制剂包含溶剂和根据权利要求1至5中的任一项或多项所述的化合物或根据权利要求6所述的低聚物、聚合物或树枝状大分子。
8.一种电子器件,所述电子器件选自有机集成电路(OIC)、有机场效应晶体管(OFET)、有机薄膜晶体管(OTFT)、有机发光晶体管(OLET)、有机光伏电池、有机光学检测器、有机光感受器、有机场猝熄器件(OFQD)、有机发光电化学电池(OLEC)、有机激光二极管(O-Laser)和有机电致发光器件(OLED),其特征在于所述电子器件包含根据权利要求1至5中的任一项或多项所述的化合物。
9.根据权利要求16所述的电子器件,其中所述电子器件是有机电致发光器件,其特征在于所述有机电致发光器件包含阳极、阴极和至少一个有机层,所述有机层包含根据权利要求1至5中的任一项或多项所述的化合物作为发光层中的基质材料与一种或多种掺杂剂组合,或者所述化合物作为电子传输材料包含在电子传输层、电子注入层或空穴阻挡层中。
10.根据权利要求1至5中的任一项或多项所述的化合物在电子器件中的用途。
11.一种制造根据权利要求8或权利要求9所述的电子器件的方法,所述方法包括以下步骤:
(a)提供根据权利要求1至5中的任一项或多项所述的化合物或者根据权利要求6所述的低聚物、聚合物或树枝状大分子;和
(b)将所述化合物或所述低聚物、聚合物或树枝状大分子沉积在支撑层上。
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- 2015-07-23 GB GBGB1513037.0A patent/GB201513037D0/en not_active Ceased
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- 2016-07-01 US US15/746,228 patent/US11581495B2/en active Active
- 2016-07-01 KR KR1020187005316A patent/KR20180030206A/ko unknown
- 2016-07-01 WO PCT/EP2016/001119 patent/WO2017012694A1/en active Application Filing
- 2016-07-01 CN CN201680040791.8A patent/CN107848969A/zh active Pending
- 2016-07-01 JP JP2018503492A patent/JP2018524819A/ja active Pending
- 2016-07-20 TW TW105122926A patent/TW201718488A/zh unknown
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US11581495B2 (en) | 2023-02-14 |
TW201718488A (zh) | 2017-06-01 |
KR20180030206A (ko) | 2018-03-21 |
GB201513037D0 (en) | 2015-09-09 |
WO2017012694A1 (en) | 2017-01-26 |
JP2018524819A (ja) | 2018-08-30 |
US20180226586A1 (en) | 2018-08-09 |
EP3325442A1 (en) | 2018-05-30 |
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