CN113402507A - 三亚苯衍生物,发光器件材料及发光器件 - Google Patents
三亚苯衍生物,发光器件材料及发光器件 Download PDFInfo
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- CN113402507A CN113402507A CN202110782424.8A CN202110782424A CN113402507A CN 113402507 A CN113402507 A CN 113402507A CN 202110782424 A CN202110782424 A CN 202110782424A CN 113402507 A CN113402507 A CN 113402507A
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- FQENSZQWKVWYPA-UHFFFAOYSA-N dibenzofuran-3-ylboronic acid Chemical compound C1=CC=C2C3=CC=C(B(O)O)C=C3OC2=C1 FQENSZQWKVWYPA-UHFFFAOYSA-N 0.000 description 1
- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- MORCTKJOZRLKHC-UHFFFAOYSA-N lithium;oxoboron Chemical compound [Li].O=[B] MORCTKJOZRLKHC-UHFFFAOYSA-N 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- DWJIJRSTYFPKGD-UHFFFAOYSA-N naphthalen-2-yl benzoate Chemical compound C=1C=C2C=CC=CC2=CC=1OC(=O)C1=CC=CC=C1 DWJIJRSTYFPKGD-UHFFFAOYSA-N 0.000 description 1
- FSKSOHSZNZOSOC-UHFFFAOYSA-N naphtho[1,2-b][1]benzofuran-8-ylboronic acid Chemical compound C1=CC=C2C(OC3=CC=C(C=C33)B(O)O)=C3C=CC2=C1 FSKSOHSZNZOSOC-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002907 osmium Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 229910052913 potassium silicate Inorganic materials 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
本发明涉及有机发光元件用三亚苯衍生物、含有三亚苯衍生物的发光器件材料及发光器件,更具体而言,涉及一种具有优异的色纯度和高亮度及发光效率的可溶性有机化合物以及使用该化合物的OLED器件。其特征在于下述通式(1)
Description
技术领域
本发明涉及有机发光元件用三亚苯衍生物、含有三亚苯衍生物的发光器件材料及发光器件,更具体而言,涉及一种具有优异的色纯度和高亮度及发光效率的可溶性有机化合物以及使用该化合物的OLED器件。
背景技术
有机电激发光二极管(Organic Light-Emitting Diode,简称为OLED)。该发光器件具有薄型且能在低驱动电压下高亮度发光以及能通过选择发光材料而进行多色发光的特征,因此倍受关注。
该研究自从由柯达公司的C.W.Tang等揭示有机薄膜元件能以高亮度发光以来,大量OLED行业研究人员对于其应用,做了很多研究和推进。有机薄膜发光器件被广泛应用在各种主显示屏等中,其实用化取得长足的进展。
尽管有机电致发光的研究进展非常迅速,但仍有很多亟待解决的问题,例如外量子效率(EQE)仍然需要提高,如何设计与合成出色纯度更高、高效电子传输/空穴阻挡新材料等等。对于有机电致发光器件来说,器件的发光量子效率是各种因素的综合反映,也是衡量器件品质的一个重要指标。
电致发光一般可以分为荧光发光和磷光发光。在荧光发光中,单线态激发状态的有机分子跃迁至基态,由此发出光。另一方面,在磷光发光中,三线态激发状态的有机分子跃迁至基态,由此发出光。
目前来看,部分有机电致发光材料由于其性能优秀,已经在商业上有所应用,但作为有机电致发光器件中的主体材料,除了三线态能级要高于客体材料,防止激子跃迁释放的能量逆传递以外,更重要的是具有良好的空穴迁移性能。目前,主体材料中同时具有高三线态能级和良好空穴迁移率的材料仍然缺乏。因此,如何设计新的性能更好的主体材料,一直是本领域技术人员亟待解决的问题。
发明内容
【发明所需要解决的问题】
如上所述,设计新的性能更好的主体材料是现阶段需要解决的问题。
本发明的目的是提供一种有机发光元件用三亚苯衍生物、含有三亚苯衍生物的发光器件材料及发光器件,更具体而言,涉及一种具有优异的色纯度和高亮度及发光效率的可溶性有机化合物以及使用该化合物的OLED器件。
本发明提供一种三亚苯衍生物,该化合物具有下述通式(1)
其中R1选自如下取代或未取代的取代基
其中,R2,R3选自如下取代或未取代的取代基
其中,R4,R5,R6,R7独立的选自氢、取代或未取代的C1-C15烷基、取代或未取代的C6~C30芳基、取代或未取代的C4~C30杂芳基、或者是它们的组合;
进一步的优选的方式是,所述的有机化合物独立地选自下列化合物
本发明还提供上述一种含三亚苯衍生物在有机发光器件中的应用。
优选的,所述有机发光器件包括阳极、阴极以及位于阳极与阴极之间的若干个有机功能层,所述的有机功能层含有所述的三亚苯衍生物。
本发明的有益效果:
本发明提供一种三亚苯衍生物,该三亚苯衍生物具有通式(1)所示结构,三亚苯结构具有中等的三线态能级,通过调节取代基基团,设计成双极性材料,使之空穴传输能力和电子传输能力得到平衡,更加有利于提升器件性能。另外三亚苯的平面性结构利于分子的堆积,有利于减少不必要的振动能量损失,实现高效的发光性能。本发明的三亚苯衍生物,制备方法简单,原料易得,能够满足工业化需求。
本发明所述的有机电致发光器件是包含有三亚苯衍生物的发光元件,该发光元件包含基板、第一电极、有机物层、第二电极以及覆盖层,优选的器件结构可包括基板,位于基板上的第一电极,位于第一电极上的有机物层,位于有机物层上的第二电极,以及位于第二电极外侧的覆盖层,本发明所述的第二电极外侧是指背离第一电极的一侧。
本发明所述的有机物层可以包含发光层、空穴注入层、空穴传输层、电子传输层、电子注入层作为有机物层的结构。所述的发光元件的有机物层可以由单层结构形成,也可以由层叠包含发光层,空穴注入层,空穴传输层,电子传输层,电子注入层在内的多层结构形成;同时,所述的有机物层还可以包含一层或多层结构,例如,所述的空穴传输层可以包含第一空穴传输层以及第二空穴传输层。在本发明的发光元件中,除了所述发光层包含有本发明所述的三亚苯衍生物外,其它层均可以使用现有公知技术的用于所述层的任何材料。
本发明的发光元件中,基板材料可选用典型的有机发光元件中使用的任何基板。可以是钠玻璃或无碱玻璃或者透明柔性基板,也可以是不透明材料如硅或不锈钢的基板,还可以是柔性聚酰亚胺薄膜。不同基板材料具有不同的性能,应用方向不同。作为本发明的空穴传输层,可通过将空穴传输材料的一种或二种以上层叠或混合的方法,或通过使用空穴传输材料和高分子粘合剂的混合物的方法来形成。空穴传输材料需要在施加了电场的电极之间高效率地传输来自正极的空穴,因此希望空穴注入效率高、能够高效率地传输注入的空穴。因此,要求空穴传输材料具有适当电离势,适当的能级并且具有大的空穴迁移率,进一步材料稳定性优异,制造及使用过程中不容易产生会成为陷阱的杂质。对满足这样的条件的物质,没有特别限定,例如可以是咔唑衍生物、三芳胺衍生物、联苯二胺衍生物、芴衍生物、酞菁类化合物、六腈六氮杂苯并菲类化合物、喹吖啶酮类化合物、苝衍生物、蒽醌类化合物、F4-TCNQ、聚苯胺、聚噻吩、聚乙烯咔唑等,但不限于此。
作为本发明的发光层材料,除了包含本发明提供的三亚苯衍生物,也可以使用和掺杂材料(也称客体材料),可包含多个掺杂材料。另外发光层可为单一的发光层,也可为横向或纵向叠加在一起的复合发光层。对于掺杂材料的种类选择,可以为荧光材料,也可以为磷光材料。对于掺杂材料的用量选择,优选0.1~70%质量,更优选为0.1~30质量%、进一步优选为1~30质量%、更进一步优选为1~20质量%、特别优选为1~10质量%。
可用于本发明的荧光掺杂材料可包括:稠合多环芳族衍生物、苯乙烯基胺衍生物、稠环胺衍生物、含硼化合物、吡咯衍生物、吲哚衍生物、咔唑衍生物等,但不限于此。可用于本发明的磷光掺杂材料可包括:重金属配合物、磷光发光性的稀土类金属配合物等,但不限于此。重金属配合物可举出例如铱配合物、铂配合物、锇配合物等;稀土类金属配合物可举出例如铽络合物、铕络合物等,但不限于此。作为本发明的电子传输材料,优选具备良好电子迁移率的物质,同时具备合适的HOMO和LUMO能级。可作为本发明的电子传输材料包括:金属配合物、氧杂噻唑衍生物、噁唑衍生物、二氮唑衍生物、氮杂苯衍生物、菲罗啉衍生物、二氮蒽衍生物、含硅杂环类化合物、含硼杂环类化合物、氰基类化合物、喹啉衍生物、苯并咪唑衍生物等,但不限于此。
作为本发明的电子传输材料,优选具有传输电子能力的物质,同时具有从阴极注入电子的效应,具有优异的薄膜形成能力。可作为本发明的电子注入材料包括:碱金属化合物,例如氧化锂、氟化锂、8-羟基喹啉锂、氧化锂硼、碳酸铯、8-羟基喹啉铯、硅酸钾、氟化钙、氧化钙、氟化镁、氧化镁;芴酮;含氮五元环衍生物,例如,噁唑衍生物、恶二唑衍生物、咪唑衍生物;金属配合物;蒽醌二甲烷、联苯醌、蒽酮衍生物等,但不限于此,这些化合物可以单独使用,也可与其他材料混合使用。作为本发明的阴极材料,优选具有低功函数的材料,以便容易地将电子注入有机层。可用于本发明的阴极材料包括:金属,例如镁、钙、钠、钾、钛、铟、钇、锂、铝、银、锡、铅,或者它们的合金;以及多层材料,例如LiF/Al或LiO 2/Al,但不限于此。
本发明所述的有机物层材料,它们在使用时,可单独成膜形成单层结构,也可和其他材料一起混合成膜形成单层结构,或者形成单独成膜的单层的层叠结构、混合成膜的单层的叠层结构、单独成膜的单层和混合成膜的单层的叠层结构,但不限于此。本发明所述的有机电致发光器件可以通过依次层叠上述的结构而制造。制造方法可使用干式成膜法、湿式成膜法等公知方法。作为干式成膜法的具体例,可举出真空蒸镀法、溅射法、等离子体法、离子电镀法等。作为湿式成膜法的具体例,可举出旋涂法、浸渍法、流延法、喷墨法等各种涂布法,但不限于此。本发明所述有机发光器件可广泛应用于面板显示、照明光源、柔性OLED、电子纸、有机太阳能电池、有机感光体或有机薄膜晶体管、指示牌、信号灯等领域。
具体实施方式
上述通式(1)所示的三亚苯衍生物的合成可以使用已知的方法进行。例如,使用镍、钯等过渡金属的交叉偶合反应。其他合成方法是使用镁或锌等过渡金属的C-C,C-N偶联生成反应。上述反应,限于反应条件温和、各种官能团的选择性优越等特点,优选Suzuki,Buchwald反应。
本发明的三亚苯衍生物用以下实施例举例说明,但并不限于这些实施例举例的三亚苯衍生物和合成方法。
本发明的初始原料和溶剂购于国药,一些常用的OLED中间体类等产品购于国内的OLED中间体厂商;各种钯催化剂,配体等购于sigma-Aldrich公司。
1H-NMR数据使用JEOL(400MHz)核磁共振仪来测定;HPLC数据使用岛津LC-20AD高效液相仪来测定。
实施例和比较例中使用物质为:
(化合物1)3,6-二(二苯并呋喃-3-基)-11,13-二苯基菲喹唑啉
(化合物20)3,6-双(9,9-二甲基-9H-芴-1-基)-11,13-二苯基菲喹唑啉
(化合物28)3-(9,9-二甲基-9H-芴-4-基)-6,11,13-三苯基菲喹唑啉
(化合物50)6-(萘-1-基)-3-(萘苯并呋喃-8-基)-11,13-二苯基菲喹唑啉
(化合物67)3,6-双(萘酚苯并呋喃-10-基)-11,13-二苯基菲喹唑啉
(化合物109)3,6-双(苯并萘酚噻吩-9-基)-11,13-二苯基菲喹唑啉
(化合物135)11,13-二苯基-3,6-双(7-苯基-7H-苯并咔唑-8-基)菲喹唑啉
(化合物155)10-(6-(萘-2-基)-11,13-二苯基菲喹唑啉-3-基)-10H-苯恶嗪
(化合物179)3-(二苯并呋喃-2-基)-6-(萘-2-基)-11,13-二苯基菲喹唑啉
(化合物181)3-(二苯并噻吩-4-基)-6-(萘-2-基)-11,13-二苯基菲喹唑啉
(化合物203)11,13-二苯基-3,6-双(9-苯基-9H-咔唑-2-基)菲并喹唑啉
(化合物239)3,6-双(萘并苯并呋喃-4-基)-11,13-二苯基菲喹唑啉
(化合物270)3,6-双(苯并萘酚噻吩-8-基)-11,13-二苯基菲喹唑啉
(化合物315)3,6-二(9H-咔唑-9-基)-11,13-二苯基菲喹唑啉
实施例1
化合物1的合成
在氩气氛下,反应瓶中加入N-(7,10-二溴三联苯-2-基)苯甲酰胺50.5克(100mmol)和2-氯吡啶12.5克(120mmol)二氯甲烷300ml,降温至-78℃,然后加入三氟甲基磺酸酐31.0克(110mmol),将反应混合物置于冰水浴中并加热至0℃.加入苯甲腈11克(110mmol)。将反应混合物加热到45℃,反应6小时,冷却至室温加入三乙胺中和三氟甲烷磺酸盐。减压去除挥发物,采用闪蒸柱层析法(洗脱液:己烷中10%乙酸乙酯),得到51.9克3,6-二溴-11,13-二苯基菲喹唑啉,收率88%,HPLC纯度99.6%。
1HNMR(DMSO):δ9.10(s,1H),8.93(s,1H),8.81(d,1H),8.35(m,2H),8.29(s,1H),8.12(s,1H),8.05~7.99(m,3H),7.80(d,2H),7.65(t,2H),7.50~7.49(m,4H)
氩气氛围下,反应器中加入3,6-二溴-11,13-二苯基菲喹唑啉59.0g(100mmol)、二苯并呋喃-3-基硼酸50.8g(240mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到65.0g的化合物1,收率85%,HPLC纯度99.3%。
1HNMR(DMSO):δ9.11(d,2H),8.93(s,1H),8.46~8.43(m,4H),8.35(d,2H),8.12(s,1H),8.03~7.98(m,4H),7.82~7.76(m,6H),7.54~7.49(m,6H),7.39~7.31(m,4H)实施例2
化合物20的合成
在氩气氛下,反应瓶中加入N-(7,10-二溴三联苯-2-基)苯甲酰胺50.5克(100mmol)和2-氯吡啶12.5克(120mmol)二氯甲烷300ml,降温至-78℃,然后加入三氟甲基磺酸酐31.0克(110mmol),将反应混合物置于冰水浴中并加热至0℃.加入苯甲腈11克(110mmol)。将反应混合物加热到45℃,反应6小时,冷却至室温加入三乙胺中和三氟甲烷磺酸盐。减压去除挥发物,采用闪蒸柱层析法(洗脱液:己烷中10%乙酸乙酯),得到51.9克3,6-二溴-11,13-二苯基菲喹唑啉,收率88%,HPLC纯度99.6%。
1HNMR(DMSO):δ9.10(s,1H),8.93(s,1H),8.81(d,1H),8.35(m,2H),8.29(s,1H),8.12(s,1H),8.05~7.99(m,3H),7.80(d,2H),7.65(t,2H),7.50~7.49(m,4H)
氩气氛围下,反应器中加入3,6-二溴-11,13-二苯基菲喹唑啉59.0g(100mmol)、(9,9-二甲基-9H-芴-1-基)硼酸57.1g(240mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到71.9g的化合物20,收率88%,HPLC纯度99.5%。
1HNMR(DMSO):δ9.11(d,2H),8.93(s,1H),8.46~8.43(m,4H),8.35(d,2H),8.12(s,1H),8.00(d,2H),7.90(d,2H),7.80(d,2H),7.68~7.65(m,4H),7.57~7.55(m,4H),7.50~7.49(m,4H),7.38(m,4H),7.28(m,4H),1.69(s,12H).
实施例3
化合物28的合成
在氩气氛下,反应瓶中加入N-(7-溴-10-氯苯并-2-基)苯甲酰胺46.0克(100mmol)和2-氯吡啶12.5克(120mmol)二氯甲烷300ml,降温至-78℃,然后加入三氟甲基磺酸酐31.0克(110mmol),将反应混合物置于冰水浴中并加热至0℃.加入苯甲腈11克(110mmol)。将反应混合物加热到45℃,反应6小时,冷却至室温加入三乙胺中和三氟甲烷磺酸盐。减压去除挥发物,采用闪蒸柱层析法(洗脱液:己烷中10%乙酸乙酯),得到46.3克6-溴-3-氯-11,13-二苯基菲喹唑啉,收率85%,HPLC纯度99.4%。
1HNMR(DMSO):δ9.10(s,1H),8.93(s,1H),8.81(d,1H),8.35(m,2H),8.29(s,1H),8.12(s,1H),8.05~7.99(m,3H),7.80(d,2H),7.65(t,2H),7.50~7.49(m,4H)
氩气氛围下,反应器中加入6-溴-3-氯-11,13-二苯基菲喹唑啉54.6g(100mmol)、苯硼酸12.1g(100mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到40.7g的3-氯-6,11,13-三苯基菲喹唑啉,收率75%,HPLC纯度99.1%。
1HNMR(DMSO):δ9.11(d,2H),8.93(s,1H),8.86(d,1H),8.46~8.43(m,2H),8.35(d,2H),8.13~8.12(d,2H),7.89(d,1H),7.80~7.75(m,4H),7.50~7.49(m,6H),7.41(m,1H).
氩气氛围下,反应器中加入3-氯-6,11,13-三苯基菲喹唑啉54.3g(100mmol)、(9,9-二甲基-9H-芴-4-基)硼酸28.6g(120mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到55.3g的化合物28,收率79%,HPLC纯度99.7%。
1HNMR(DMSO):δ9.11(d,2H),8.93(s,1H),8.46~8.43(m,4H),8.35(d,2H),8.12(s,1H),7.90(d,1H),7.80~7.75(m,5H),7.65(m,3H),7.55~7.49(m,7H),7.47~7.41(m,2H),1.69(s,6H).
实施例4
化合物50的合成
在氩气氛下,反应瓶中加入N-(7-溴-10-氯苯并-2-基)苯甲酰胺46.0克(100mmol)和2-氯吡啶12.5克(120mmol)二氯甲烷300ml,降温至-78℃,然后加入三氟甲基磺酸酐31.0克(110mmol),将反应混合物置于冰水浴中并加热至0℃.加入苯甲腈11克(110mmol)。将反应混合物加热到45℃,反应6小时,冷却至室温加入三乙胺中和三氟甲烷磺酸盐。减压去除挥发物,采用闪蒸柱层析法(洗脱液:己烷中10%乙酸乙酯),得到46.3克6-溴-3-氯-11,13-二苯基菲喹唑啉,收率85%,HPLC纯度99.4%。
1HNMR(DMSO):δ9.10(s,1H),8.93(s,1H),8.81(d,1H),8.35(m,2H),8.29(s,1H),8.12(s,1H),8.05~7.99(m,3H),7.80(d,2H),7.65(t,2H),7.50~7.49(m,4H)
氩气氛围下,反应器中加入6-溴-3-氯-11,13-二苯基菲喹唑啉54.6g(100mmol)、1-萘硼酸172.0g(100mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到42.7g的3-氯-6-(萘-1-基)-11,13-二苯基菲喹唑啉,收率72%,HPLC纯度99.1%。
1HNMR(DMSO):δ9.11(d,2H),8.95~8.93(m,2H),8.86(d,1H),8.50(d,1H),8.46~8.43(m,2H),8.35(d,2H),8.20(d,1H),8.13~8.12(d,2H),8.09(d,1H),7.89(d,1H),7.80~7.77(m,3H),7.65(m,2H),7.52~7.49(m,5H),7.39(d,1H).
氩气氛围下,反应器中加入3-氯-6-(萘-1-基)-11,13-二苯基菲喹唑啉59.3g(100mmol)、萘并[1,2-b]苯并呋喃-8-基硼酸31.4g(120mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到62.8g的化合物50,收率81%,HPLC纯度99.5%。
1HNMR(DMSO):δ9.11(d,2H),8.95~8.93(m,2H),8.50(d,1H),8.46~8.43(m,4H),8.35(d,2H),8.20~8.16(m,2H),8.12~8.11(d,2H),8.09(d,1H),7.88~7.83(m,3H),7.80~7.77(m,4H),7.69~7.65(m,4H),7.52~7.48(m,6H),7.39(m,1H).
实施例5
化合物67的合成
在氩气氛下,反应瓶中加入N-(7,10-二溴三联苯-2-基)苯甲酰胺50.5克(100mmol)和2-氯吡啶12.5克(120mmol)二氯甲烷300ml,降温至-78℃,然后加入三氟甲基磺酸酐31.0克(110mmol),将反应混合物置于冰水浴中并加热至0℃.加入苯甲腈11克(110mmol)。将反应混合物加热到45℃,反应6小时,冷却至室温加入三乙胺中和三氟甲烷磺酸盐。减压去除挥发物,采用闪蒸柱层析法(洗脱液:己烷中10%乙酸乙酯),得到51.9克3,6-二溴-11,13-二苯基菲喹唑啉,收率88%,HPLC纯度99.6%。
1HNMR(DMSO):δ9.10(s,1H),8.93(s,1H),8.81(d,1H),8.35(m,2H),8.29(s,1H),8.12(s,1H),8.05~7.99(m,3H),7.80(d,2H),7.65(t,2H),7.50~7.49(m,4H)
氩气氛围下,反应器中加入3,6-二溴-11,13-二苯基菲喹唑啉59.0g(100mmol)、萘并苯并呋喃-10-基硼酸62.9g(240mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到72.7g的化合物67,收率84%,HPLC纯度99.3%。
1HNMR(DMSO):δ9.11(d,2H),8.93(s,1H),8.46~8.43(m,4H),8.35(d,2H),8.16(d,2H),8.12~8.11(m,3H),8.08(d,2H),8.02(m,2H),7.84~7.80(m,4H),7.69~7.67(m,4H),7.65(d,2H),7.51~7.48(m,8H).
实施例6
化合物109的合成
在氩气氛下,反应瓶中加入N-(7,10-二溴三联苯-2-基)苯甲酰胺50.5克(100mmol)和2-氯吡啶12.5克(120mmol)二氯甲烷300ml,降温至-78℃,然后加入三氟甲基磺酸酐31.0克(110mmol),将反应混合物置于冰水浴中并加热至0℃.加入苯甲腈11克(110mmol)。将反应混合物加热到45℃,反应6小时,冷却至室温加入三乙胺中和三氟甲烷磺酸盐。减压去除挥发物,采用闪蒸柱层析法(洗脱液:己烷中10%乙酸乙酯),得到51.9克3,6-二溴-11,13-二苯基菲喹唑啉,收率88%,HPLC纯度99.6%。
1HNMR(DMSO):δ9.10(s,1H),8.93(s,1H),8.81(d,1H),8.35(m,2H),8.29(s,1H),8.12(s,1H),8.05~7.99(m,3H),7.80(d,2H),7.65(t,2H),7.50~7.49(m,4H)
氩气氛围下,反应器中加入3,6-二溴-11,13-二苯基菲喹唑啉59.0g(100mmol)、苯并萘酚噻吩-9-基硼酸66.8g(240mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到74.5g的化合物109,收率83%,HPLC纯度99.4%。
1HNMR(DMSO):δ9.11(d,2H),8.93(s,1H),8.54(m,2H),8.46~8.43(m,4H),8.35(d,2H),8.24~8.17(m,6H),7.99(d,2H),7.80~7.78(m,6H),7.65~7.61(m,4H),7.53~7.50(m,5H).
实施例7
化合物135的合成
在氩气氛下,反应瓶中加入N-(7,10-二溴三联苯-2-基)苯甲酰胺50.5克(100mmol)和2-氯吡啶12.5克(120mmol)二氯甲烷300ml,降温至-78℃,然后加入三氟甲基磺酸酐31.0克(110mmol),将反应混合物置于冰水浴中并加热至0℃.加入苯甲腈11克(110mmol)。将反应混合物加热到45℃,反应6小时,冷却至室温加入三乙胺中和三氟甲烷磺酸盐。减压去除挥发物,采用闪蒸柱层析法(洗脱液:己烷中10%乙酸乙酯),得到51.9克3,6-二溴-11,13-二苯基菲喹唑啉,收率88%,HPLC纯度99.6%。
1HNMR(DMSO):δ9.10(s,1H),8.93(s,1H),8.81(d,1H),8.35(m,2H),8.29(s,1H),8.12(s,1H),8.05~7.99(m,3H),7.80(d,2H),7.65(t,2H),7.50~7.49(m,4H)
氩气氛围下,反应器中加入3,6-二溴-11,13-二苯基菲喹唑啉59.0g(100mmol)、(7-苯基-7H-苯并咔唑-8-基)硼酸80.9g(240mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到87.4g的化合物135,收率86%,HPLC纯度99.5%。
1HNMR(DMSO):δ9.11(d,2H),8.93(s,1H),8.54(m,2H),8.46~8.43(m,4H),8.35(d,2H),8.29(d,2H),8.12(s,1H),8.06~7.94(m,8H),7.80(d,2H),7.65~7.61(m,7H),7.58(d,2H),7.53(d,2H),7.50(m,7H),7.48(m,2H).
实施例8
化合物155的合成
在氩气氛下,反应瓶中加入N-(7-溴-10-氯苯并-2-基)苯甲酰胺46.0克(100mmol)和2-氯吡啶12.5克(120mmol)二氯甲烷300ml,降温至-78℃,然后加入三氟甲基磺酸酐31.0克(110mmol),将反应混合物置于冰水浴中并加热至0℃.加入苯甲腈11克(110mmol)。将反应混合物加热到45℃,反应6小时,冷却至室温加入三乙胺中和三氟甲烷磺酸盐。减压去除挥发物,采用闪蒸柱层析法(洗脱液:己烷中10%乙酸乙酯),得到46.3克6-溴-3-氯-11,13-二苯基菲喹唑啉,收率85%,HPLC纯度99.4%。
1HNMR(DMSO):δ9.10(s,1H),8.93(s,1H),8.81(d,1H),8.35(m,2H),8.29(s,1H),8.12(s,1H),8.05~7.99(m,3H),7.80(d,2H),7.65(t,2H),7.50~7.49(m,4H)
氩气氛围下,反应器中加入6-溴-3-氯-11,13-二苯基菲喹唑啉54.6g(100mmol)、2-萘硼酸172.0g(100mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到42.7g的3-氯-6-(萘-1-基)-11,13-二苯基菲喹唑啉,收率72%,HPLC纯度99.1%。
1HNMR(DMSO):δ9.11(d,2H),8.93(d,1H),8.86(d,1H),8.46~8.43(m,2H),8.35(d,2H),8.13~8.12(m,2H),8.09~7.99(m,3H),7.89(m,1H),7.80(m,2H),7.65~7.63(m,3H),7.60(m,1H),7.55(d,1H),7.50~7.49(m,4H),7.38(d,1H).
在氩气氛下,反应容器中加入叔丁醇钾26.9克(240mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克(1mmol%)3-氯-6-(萘-1-基)-11,13-二苯基菲喹唑啉59.3g(100mmol),10H苯恶嗪22.0克(120mmol)和1000mL乙二醇二甲醚(DME),在80℃加热搅拌15小时。反应混合物冷却到室温,加入500ml水,过滤,粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/己烷),得到59.9克化合物155,HPLC纯度99.3%,收率81%.
1HNMR(DMSO):δ9.11(d,2H),8.93(d,1H),8.88(d,1H),8.46~8.43(m,2H),8.35(d,2H),8.12(s,1H),8.09~8.06(m,2H),7.99(d,1H),7.90(s,1H),7.80(d,2H),7.66~7.63(m,4H),7.60(m,1H),7.50~7.49(m,4H),7.38(d,1H),7.14(d,2H),7.01~6.96(m,6H).
实施例9
化合物179的合成
在氩气氛下,反应瓶中加入N-(7-溴-10-氯苯并-2-基)苯甲酰胺46.0克(100mmol)和2-氯吡啶12.5克(120mmol)二氯甲烷300ml,降温至-78℃,然后加入三氟甲基磺酸酐31.0克(110mmol),将反应混合物置于冰水浴中并加热至0℃.加入苯甲腈11克(110mmol)。将反应混合物加热到45℃,反应6小时,冷却至室温加入三乙胺中和三氟甲烷磺酸盐。减压去除挥发物,采用闪蒸柱层析法(洗脱液:己烷中10%乙酸乙酯),得到46.3克6-溴-3-氯-11,13-二苯基菲喹唑啉,收率85%,HPLC纯度99.4%。
1HNMR(DMSO):δ9.10(s,1H),8.93(s,1H),8.81(d,1H),8.35(m,2H),8.29(s,1H),8.12(s,1H),8.05~7.99(m,3H),7.80(d,2H),7.65(t,2H),7.50~7.49(m,4H)
氩气氛围下,反应器中加入6-溴-3-氯-11,13-二苯基菲喹唑啉54.6g(100mmol)、2-萘硼酸172.0g(100mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到42.7g的3-氯-6-(萘-1-基)-11,13-二苯基菲喹唑啉,收率72%,HPLC纯度99.1%。
1HNMR(DMSO):δ9.11(d,2H),8.93(d,1H),8.86(d,1H),8.46~8.43(m,2H),8.35(d,2H),8.13~8.12(m,2H),8.09~7.99(m,3H),7.89(m,1H),7.80(m,2H),7.65~7.63(m,3H),7.60(m,1H),7.55(d,1H),7.50~7.49(m,4H),7.38(d,1H).
在氩气氛下,反应容器中加入3-氯-6-(萘-1-基)-11,13-二苯基菲喹唑啉59.3克(100mmol),二苯并呋喃-2-基硼酸25.4g(120mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入800ml水,固体析出,过滤,得到的固体用乙醇洗涤,500ml甲苯重结晶得到58.0g化合物179,收率80%,HPLC纯度99.5%。1HNMR(DMSO):δ9.11(d,2H),8.93(d,1H),8.46~8.43(m,2H),8.35(d,2H),
8.12(s,1H),8.09~7.99(m,3H),7.98(d,1H),7.88~7.83(m,2H),7.80~7.79(m,3H),7.65~7.63(m,3H),7.60(m,1H),7.50~7.49(m,4H),7.39~7.38(m,2H),7.31(m,1H).
实施例10
化合物181的合成
在氩气氛下,反应瓶中加入N-(7-溴-10-氯苯并-2-基)苯甲酰胺46.0克(100mmol)和2-氯吡啶12.5克(120mmol)二氯甲烷300ml,降温至-78℃,然后加入三氟甲基磺酸酐31.0克(110mmol),将反应混合物置于冰水浴中并加热至0℃.加入苯甲腈11克(110mmol)。将反应混合物加热到45℃,反应6小时,冷却至室温加入三乙胺中和三氟甲烷磺酸盐。减压去除挥发物,采用闪蒸柱层析法(洗脱液:己烷中10%乙酸乙酯),得到46.3克6-溴-3-氯-11,13-二苯基菲喹唑啉,收率85%,HPLC纯度99.4%。
1HNMR(DMSO):δ9.10(s,1H),8.93(s,1H),8.81(d,1H),8.35(m,2H),8.29(s,1H),8.12(s,1H),8.05~7.99(m,3H),7.80(d,2H),7.65(t,2H),7.50~7.49(m,4H)
氩气氛围下,反应器中加入6-溴-3-氯-11,13-二苯基菲喹唑啉54.6g(100mmol)、2-萘硼酸172.0g(100mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到42.7g的3-氯-6-(萘-1-基)-11,13-二苯基菲喹唑啉,收率72%,HPLC纯度99.1%。
1HNMR(DMSO):δ9.11(d,2H),8.93(d,1H),8.86(d,1H),8.46~8.43(m,2H),8.35(d,2H),8.13~8.12(m,2H),8.09~7.99(m,3H),7.89(m,1H),7.80(m,2H),7.65~7.63(m,3H),7.60(m,1H),7.55(d,1H),7.50~7.49(m,4H),7.38(d,1H).
在氩气氛下,反应容器中加入3-氯-6-(萘-1-基)-11,13-二苯基菲喹唑啉59.3克(100mmol),二苯并噻吩-4-基硼酸27.3g(120mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入800ml水,固体析出,过滤,得到的固体用乙醇洗涤,500ml甲苯重结晶得到63.0g化合物181,收率85%,HPLC纯度99.3%。
1HNMR(DMSO):δ9.11(d,2H),8.93(d,1H),8.55(m,1H),8.46~8.43(m,5H),8.35~8.32(m,3H),8.12(s,1H),8.09~7.99(m,3H),7.93(d,1H),7.80(m,2H),7.70(m,1H),7.65~7.63(m,3H),7.60(m,1H),7.56~7.55(m,2H),7.50~7.49(m,5H),7.38(d,1H).
实施例11
化合物203的合成
在氩气氛下,反应瓶中加入N-(7,10-二溴三联苯-2-基)苯甲酰胺50.5克(100mmol)和2-氯吡啶12.5克(120mmol)二氯甲烷300ml,降温至-78℃,然后加入三氟甲基磺酸酐31.0克(110mmol),将反应混合物置于冰水浴中并加热至0℃.加入苯甲腈11克(110mmol)。将反应混合物加热到45℃,反应6小时,冷却至室温加入三乙胺中和三氟甲烷磺酸盐。减压去除挥发物,采用闪蒸柱层析法(洗脱液:己烷中10%乙酸乙酯),得到51.9克3,6-二溴-11,13-二苯基菲喹唑啉,收率88%,HPLC纯度99.6%。
1HNMR(DMSO):δ9.10(s,1H),8.93(s,1H),8.81(d,1H),8.35(m,2H),8.29(s,1H),8.12(s,1H),8.05~7.99(m,3H),7.80(d,2H),7.65(t,2H),7.50~7.49(m,4H)
氩气氛围下,反应器中加入3,6-二溴-11,13-二苯基菲喹唑啉59.0g(100mmol)、(9-苯基-9H-咔唑-2-基)硼酸68.9g(240mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到73.2g的化合物203,收率80%,HPLC纯度99.3%。
1HNMR(DMSO):δ9.11(d,2H),8.93(s,1H),8.55(d,2H),8.46~8.43(m,4H),8.35(d,2H),8.31(d,2H),8.12(s,1H),7.94~7.91(m,4H),7.80(d,2H),7.74(s,2H),7.65~7.62(m,6H),7.58(m,2H),7.50~7.49(m,8H),7.35(d,2H),7.16(d,2H).
实施例12
化合物239的合成
在氩气氛下,反应瓶中加入N-(7,10-二溴三联苯-2-基)苯甲酰胺50.5克(100mmol)和2-氯吡啶12.5克(120mmol)二氯甲烷300ml,降温至-78℃,然后加入三氟甲基磺酸酐31.0克(110mmol),将反应混合物置于冰水浴中并加热至0℃.加入苯甲腈11克(110mmol)。将反应混合物加热到45℃,反应6小时,冷却至室温加入三乙胺中和三氟甲烷磺酸盐。减压去除挥发物,采用闪蒸柱层析法(洗脱液:己烷中10%乙酸乙酯),得到51.9克3,6-二溴-11,13-二苯基菲喹唑啉,收率88%,HPLC纯度99.6%。
1HNMR(DMSO):δ9.10(s,1H),8.93(s,1H),8.81(d,1H),8.35(m,2H),8.29(s,1H),8.12(s,1H),8.05~7.99(m,3H),7.80(d,2H),7.65(t,2H),7.50~7.49(m,4H)
氩气氛围下,反应器中加入3,6-二溴-11,13-二苯基菲喹唑啉59.0g(100mmol)、萘并苯并呋喃-4-基硼酸62.9g(240mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到70.9g的化合物239,收率82%,HPLC纯度99.5%。
1HNMR(DMSO):δ9.11(d,2H),8.93(s,1H),8.46~8.43(m,4H),8.35(d,2H),8.28(d,2H),8.12(s,1H),8.11~8.02(m,6H),7.80(d,2H),7.75(d,2H),7.51~7.50(m,5H),7.49(s,2H),7.42(s,2H).
实施例13
化合物270的合成
在氩气氛下,反应瓶中加入N-(7,10-二溴三联苯-2-基)苯甲酰胺50.5克(100mmol)和2-氯吡啶12.5克(120mmol)二氯甲烷300ml,降温至-78℃,然后加入三氟甲基磺酸酐31.0克(110mmol),将反应混合物置于冰水浴中并加热至0℃.加入苯甲腈11克(110mmol)。将反应混合物加热到45℃,反应6小时,冷却至室温加入三乙胺中和三氟甲烷磺酸盐。减压去除挥发物,采用闪蒸柱层析法(洗脱液:己烷中10%乙酸乙酯),得到51.9克3,6-二溴-11,13-二苯基菲喹唑啉,收率88%,HPLC纯度99.6%。
1HNMR(DMSO):δ9.10(s,1H),8.93(s,1H),8.81(d,1H),8.35(m,2H),8.29(s,1H),8.12(s,1H),8.05~7.99(m,3H),7.80(d,2H),7.65(t,2H),7.50~7.49(m,4H)
氩气氛围下,反应器中加入3,6-二溴-11,13-二苯基菲喹唑啉59.0g(100mmol)、萘并苯并呋喃-4-基硼酸66.8g(240mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到74.5g的化合物270,收率83%,HPLC纯度99.5%。
1HNMR(DMSO):δ9.11(d,2H),8.93(s,1H),8.55~8.54(m,4H),8.46~8.43(m,4H),8.35(d,2H),8.32(d,2H),8.12(s,1H),7.99(m,2H),7.80(m,4H),7.78(d,2H),7.70(d,2H),7.65~7.61(m,4H),7.53(m,2H),7.50(m,3H).
实施例14
化合物315的合成
在氩气氛下,反应瓶中加入N-(7,10-二溴三联苯-2-基)苯甲酰胺50.5克(100mmol)和2-氯吡啶12.5克(120mmol)二氯甲烷300ml,降温至-78℃,然后加入三氟甲基磺酸酐31.0克(110mmol),将反应混合物置于冰水浴中并加热至0℃.加入苯甲腈11克(110mmol)。将反应混合物加热到45℃,反应6小时,冷却至室温加入三乙胺中和三氟甲烷磺酸盐。减压去除挥发物,采用闪蒸柱层析法(洗脱液:己烷中10%乙酸乙酯),得到51.9克3,6-二溴-11,13-二苯基菲[9,10-g]喹唑啉,收率88%,HPLC纯度99.6%。
1HNMR(DMSO):δ9.10(s,1H),8.93(s,1H),8.81(d,1H),8.35(m,2H),8.29(s,1H),8.12(s,1H),8.05~7.99(m,3H),7.80(d,2H),7.65(t,2H),7.50~7.49(m,4H)
在氩气氛下,反应容器中加入叔丁醇钾26.9克(240mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克(1mmol%)3,6-二溴-11,13-二苯基菲[9,10-g]喹唑啉59.0g(100mmol),咔唑40.1克(200mmol)和1000mL乙二醇二甲醚(DME),在80℃加热搅拌15小时。反应混合物冷却到室温,加入500ml水,过滤,粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/己烷),得到61.0克3,6-二(9H-咔唑-9-基)-11,13-二苯基菲[9,10-g]喹唑啉,HPLC纯度99.5%,收率80%.
1HNMR(DMSO):δ9.05(d,2H),8.93(s,1H),8.55(d,2H),8.35(d,2H),8.25~8.24(m,2H),8.19(m,2H),8.11(m,3H),8.00(m,1H),7.94(d,2H),7.80(m,2H)7.65(m,2H),7.58(m,2H),7.50~7.49(m,6H),7.35(d,2H),7.20(d,2H),7.16(d,2H).
器件实施方案
发光材料器件的评价
器件实施例中所用的各有机层化合物如下所示:
实施例15
器件制备方式:
器件的基本结构模型为:ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/EML:RD(Ir配合物)(40nm)=94:6/ETL(30nm)/LiF(1nm)/Al(80nm)
依次使用丙酮、乙醇和蒸馏水对透明阳极氧化铟锡(ITO)20(10Ω/sq)玻璃基板进行超声清洗,再用臭氧等离子处理15分钟。
然后在真空气相蒸镀设备的衬底固定器上安装ITO衬底。在蒸镀设备中,控制体系压力在10-6托。向ITO衬底上蒸发厚度为60nm的空穴传输层材料HAT-CN。
然后蒸发厚度为40nm的发光层材料EML(化合物1),其中掺杂不同质量分数的RD金属铱配合物掺杂剂。
然后蒸发厚度为30nm的电子传输层材料ETL。
然后蒸发厚度为1nm的LiF为电子注入层。
最后蒸发厚度为80nm的Al作为阴极,利用玻璃封装盖对器件进行封装。
实施例16
除了EML材料为化合物20以外,其余与实施例20作成相同的元件进行评价,测试结果见表1。
实施例17
除了EML材料为化合物28以外,其余与实施例20作成相同的元件进行评价,测试结果见表1。
实施例18
除了EML材料为化合物50以外,其余与实施例20作成相同的元件进行评价,测试结果见表1。
实施例19
除了EML材料为化合物67以外,其余与实施例20作成相同的元件进行评价,测试结果见表1。
实施例20
除了EML材料为化合物109以外,其余与实施例20作成相同的元件进行评价,测试结果见表1。
实施例21
除了EML材料为化合物135以外,其余与实施例20作成相同的元件进行评价,测试结果见表1。
实施例22
除了EML材料为化合物155以外,其余与实施例20作成相同的元件进行评价,测试结果见表1。
实施例23
除了EML材料为化合物179以外,其余与实施例20作成相同的元件进行评价,测试结果见表1。
实施例24
除了EML材料为化合物181以外,其余与实施例20作成相同的元件进行评价,测试结果见表1。
实施例25
除了EML材料为化合物203以外,其余与实施例20作成相同的元件进行评价,测试结果见表1。
实施例26
除了EML材料为化合物239以外,其余与实施例20作成相同的元件进行评价,测试结果见表1。
实施例27
除了EML材料为化合物270以外,其余与实施例20作成相同的元件进行评价,测试结果见表1。
实施例28
除了EML材料为化合物315以外,其余与实施例20作成相同的元件进行评价,测试结果见表1。
对比例1
除了EML材料为化合物RH-01以外,其余与实施例20作成相同的元件进行评价,测试结果见表1。
对比例2
除了EML材料为化合物RH-02以外,其余与实施例20作成相同的元件进行评价,测试结果见表1。
【表1】
序号 | 主体材料 | 电流(mA/cm<sup>2</sup>) | 电流效率(cd/A) | LT98(hr) |
实施例15 | 1 | 10 | 16.8 | 11.0 |
实施例16 | 20 | 10 | 16.1 | 11.8 |
实施例17 | 28 | 10 | 16.7 | 12.1 |
实施例18 | 50 | 10 | 15.9 | 13.3 |
实施例19 | 67 | 10 | 14.8 | 12.3 |
实施例20 | 109 | 10 | 16.5 | 14.2 |
实施例21 | 135 | 10 | 15.9 | 11.9 |
实施例22 | 155 | 10 | 14.7 | 12.3 |
实施例23 | 179 | 10 | 16.9 | 11.8 |
实施例24 | 181 | 10 | 17.1 | 12.8 |
实施例25 | 203 | 10 | 16.3 | 11.7 |
实施例26 | 239 | 10 | 15.4 | 11.6 |
实施例27 | 270 | 10 | 15.9 | 12.3 |
实施例28 | 315 | 10 | 15.3 | 12.6 |
对比例1 | RH01 | 10 | 9.7 | 10.8 |
对比例2 | RH02 | 10 | 8.2 | 10.7 |
器件结构除了发光层不同外,其它均一致,基于RH-01和RH-02的器件性能为参考,三亚苯衍生物的电流效率有了显著提升,同时器件寿命也有所提升。综上所述,本发明所制备的新型三亚苯衍生物有机材料,在有机发光二极管上具有有较大的应用价值。
Claims (8)
3.一种有机光电器件,其特征在于,包括:
第一电极;
第二电极,与所述第一电极相面对;
有机功能层,夹设于所述第一电极和所述第二电极之间;
其中,有机功能层包含权利要求1-2中所述的三亚苯衍生物。
4.根据权利要求3所述的有机光电器件,其特征在于,有机光电器件为有机光伏器件、有机发光器件(OLED)、有机太阳电池(OSC)、电子纸(e-paper)、有机感光体(OPC)、有机薄膜晶体管(OTFT)及有机内存器件(Organic Memory Element)、照明和显示装置。
5.一种有机光电元件,包括阴极层、阳极层和有机层,该有机层包括空穴注入层、空穴传输层、发光层或活性层、电子注入层、电子传输层中至少一层,其特征在于:该器件的任一层中含有权利要求1-2所述的三亚苯衍生物。
6.根据权利要求3或5所述的有机光电元件为有机电致发光器件,其特征在于,发光层中含有所述有机化合物和相应的客体材料,其中所述有机化合物的质量百分数在1%至99%,客体材料没有任何限制。
7.根据权利要求3或5所述的有机光电元件为有机电致发光器件,其特征在于,电子传输层中含有所述有机化合物,其中所述有机化合物的质量百分数在1%至100%。
8.一种显示或照明装置,其特征在于,所述的显示或照明装置含有权利要求3至7所述的有机光电元件。
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CN114591301A (zh) * | 2022-03-31 | 2022-06-07 | 武汉天马微电子有限公司 | 一种有机化合物及其电致发光的应用 |
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