CN105777649B - The gathering induced luminescence material of triphenylethylene base substitution phenanthro- imdazole derivatives and its application in organic electroluminescence device is prepared - Google Patents
The gathering induced luminescence material of triphenylethylene base substitution phenanthro- imdazole derivatives and its application in organic electroluminescence device is prepared Download PDFInfo
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- CN105777649B CN105777649B CN201610191626.4A CN201610191626A CN105777649B CN 105777649 B CN105777649 B CN 105777649B CN 201610191626 A CN201610191626 A CN 201610191626A CN 105777649 B CN105777649 B CN 105777649B
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- bromobenzaldehyde
- phenanthroimidazole
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- 239000000463 material Substances 0.000 title claims abstract description 28
- 238000004020 luminiscence type Methods 0.000 title claims abstract description 5
- 238000005401 electroluminescence Methods 0.000 title abstract description 7
- MKYQPGPNVYRMHI-UHFFFAOYSA-N Triphenylethylene Chemical group C=1C=CC=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 MKYQPGPNVYRMHI-UHFFFAOYSA-N 0.000 title abstract description 4
- 230000037429 base substitution Effects 0.000 title 1
- GZPPANJXLZUWHT-UHFFFAOYSA-N 1h-naphtho[2,1-e]benzimidazole Chemical class C1=CC2=CC=CC=C2C2=C1C(N=CN1)=C1C=C2 GZPPANJXLZUWHT-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000004220 aggregation Methods 0.000 claims abstract description 18
- 230000002776 aggregation Effects 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 239000010410 layer Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 22
- 239000007787 solid Substances 0.000 abstract description 5
- 238000010791 quenching Methods 0.000 abstract description 2
- 230000000171 quenching effect Effects 0.000 abstract description 2
- 238000005286 illumination Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 113
- 230000015572 biosynthetic process Effects 0.000 description 106
- 238000003786 synthesis reaction Methods 0.000 description 106
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 92
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- 238000004949 mass spectrometry Methods 0.000 description 56
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- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 39
- 229940125904 compound 1 Drugs 0.000 description 30
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 26
- 229940125877 compound 31 Drugs 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 description 20
- NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical compound BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 14
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 14
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- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 9
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- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 7
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 239000011541 reaction mixture Substances 0.000 description 6
- DPKTVUKEPNBABS-UHFFFAOYSA-N 3-tert-butylaniline Chemical compound CC(C)(C)C1=CC=CC(N)=C1 DPKTVUKEPNBABS-UHFFFAOYSA-N 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- -1 3,6-diphenylphenanthrenequinone Chemical compound 0.000 description 3
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- 229940043376 ammonium acetate Drugs 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
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- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 3
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
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Abstract
一种三苯乙烯基取代菲并咪唑衍生物的聚集诱导发光材料及其在制备有机电致发光器件中的应用，属于有机电致发光技术领域。该发光材料结构式如下所示，其突出特点是将菲并咪唑基团和三苯乙烯基团通过一个苯环连接在一起，该类分子不仅继承了菲并咪唑良好的热稳定性，较高的电子迁移率和较高的荧光量子效率等优点，而且也继承了三苯乙烯基团聚集诱导发光的性质，克服了聚集引起荧光淬灭问题。同时，分子具有较大的扭曲结构，能够保证化合物在固态时的具有很高的荧光量子效率，利用该类材料作为发光层制备的电致发光器件具有优良的性能，该电致发光器件用于制备照明光源或平板显示器。
The invention relates to an aggregation-induced luminescent material of tristyryl-substituted phenanthroimidazole derivatives and its application in the preparation of organic electroluminescence devices, belonging to the technical field of organic electroluminescence. The structural formula of the luminescent material is as follows. Its outstanding feature is that the phenanthroimidazole group and the triphenylethylene group are connected together through a benzene ring. This type of molecule not only inherits the good thermal stability of phenanthroimidazole, but also has a high It has the advantages of electron mobility and high fluorescence quantum efficiency, and also inherits the property of triphenylethylene group aggregation-induced luminescence, which overcomes the problem of fluorescence quenching caused by aggregation. At the same time, the molecule has a large twisted structure, which can ensure the high fluorescence quantum efficiency of the compound in the solid state. The electroluminescent device prepared by using this type of material as the light-emitting layer has excellent performance. The electroluminescent device is used for Prepare a light source for illumination or a flat panel display.
Description
技术领域technical field
本发明属于有机电致发光技术领域，具体涉及一类三苯乙烯基取代菲并咪唑衍生物的聚集诱导发光材料及其在制备有机电致发光器件中的应用。The invention belongs to the technical field of organic electroluminescence, and in particular relates to a kind of aggregation-induced luminescent material of tristyryl-substituted phenanthroimidazole derivatives and its application in preparing organic electroluminescent devices.
背景技术Background technique
Pope等人于二十世纪六十年代初最早报道了有机电致发光现象，他们在蒽单晶两侧施加四百伏的高压时观察到了蒽发出的蓝光。但是由于单晶难于生长，器件驱动电压很高(400～2000V)，他们所采用的工艺几乎没有实际用途。直到1987年，美国Kodak公司的C.W.Tang等人采用超薄膜技术以空穴传输效果较好的芳香胺作为空穴传输层，以8-羟基喹啉的铝配合物作为发光层，以氧化铟锡(ITO)薄膜和金属合金分别作为阳极和阴极，制备了发光器件。该器件在10V驱动电压下得到了亮度高达1000cd/m2的绿光发射，器件的效率为1.5lm/W(见C.W.TangandS.A.VanSlyke，Appl.Phys.Lett.，1987，51，913)。这一突破性进展使得有机电致发光研究得以在世界范围内迅速深入地开展起来。Pope et al first reported the phenomenon of organic electroluminescence in the early 1960s. They observed the blue light emitted by anthracene when a high voltage of 400 volts was applied to both sides of anthracene single crystal. However, because single crystals are difficult to grow and the driving voltage of the device is very high (400-2000V), the technology they use has almost no practical application. Until 1987, CW Tang et al. of Kodak Corporation of the United States used ultra-thin film technology to use aromatic amines with better hole transport effects as the hole transport layer, aluminum complexes of 8-hydroxyquinoline as the light-emitting layer, and indium tin oxide ( ITO) films and metal alloys were used as anode and cathode, respectively, to prepare light-emitting devices. The device has a green light emission with a brightness of up to 1000cd/ m2 at a driving voltage of 10V, and the efficiency of the device is 1.5lm/W (see CW Tang and S.A. Van Slyke, Appl. Phys. Lett., 1987, 51, 913). This breakthrough has enabled the research of organic electroluminescence to be carried out rapidly and deeply all over the world.
新材料在有机电致发光器件中的应用是推动电致发光技术不断进步并进入实用化阶段的必需手段。近年来，人们对新材料的开发投入了巨大的财力和精力，大量性能优良的材料使有机电致发光取得了一些突破性进展(见U.S.Pat.No.5，150，006；5，141，671；5，073，446；5，061，569；5，059，862；5，059，861；5，047，687；4，950，950；5，104，740；5，227，252；5，256，945；5，069，975；5，122，711；5，554，450；5，683，823；5，593，788；5，645，948；5，451，343；5，623，080；5，395，862)。The application of new materials in organic electroluminescent devices is a necessary means to promote the continuous progress of electroluminescent technology and enter the practical stage. In recent years, people have invested huge financial resources and energy in the development of new materials, and a large number of materials with excellent properties have made some breakthroughs in organic electroluminescence (see U.S. Pat. No. 5, 150, 006; 5, 141, 671; 5,073,446; 5,061,569; 5,059,862; 5,059,861; 5,047,687; 4,950,950; 5,104,740; 5,227,252; 5,256,945; 5,069,975; 5,122,711; 5,554,450; 5,683,823; 5,593,788; 5,645,948; 5,451,343; 5, 623,080; 5,395,862).
2001年，Tang等人发现了一种新的化合物，1-甲基-1,2,3,4,5-五苯基硅杂环戊二烯(见Chem.Commun.2001,1740)，当该种有机分子溶解在有机溶剂中时，几乎不发光，而当处于固体粉末、薄膜或颗粒状态时(即聚集状态时)，却表现出极强的荧光，Tang等人将这种在溶液中不发光，或者发光强度很弱，而在聚集状态时呈现强发光的现象命名为聚集诱导发光(AIE:aggregation induced emission)。这一发现，为设计合成高发光效率有机固体材料提供了有效途径，为有机发光材料的进一步发展注入了新的活力，因此，对聚集诱导发光材料的研究成为目前产业界和科学界的一大热点。In 2001, Tang et al. discovered a new compound, 1-methyl-1,2,3,4,5-pentaphenylsilacyclopentadiene (see Chem.Commun.2001,1740), when When this kind of organic molecule is dissolved in an organic solvent, it hardly emits light, but when it is in the state of solid powder, film or particle (that is, when it is aggregated), it shows extremely strong fluorescence. Tang et al. The phenomenon of no light emission, or very weak light emission intensity, but strong light emission in the aggregated state is named aggregation induced emission (AIE: aggregation induced emission). This discovery provides an effective way to design and synthesize organic solid materials with high luminous efficiency, and injects new vitality into the further development of organic luminescent materials. Therefore, the research on aggregation-induced luminescent materials has become a major industry and scientific research field hot spot.
近年来，随着在全色显示和固态白光照明领域展示出巨大的应用前景，有机电致发光技术在科研界以及产业界都得到了广泛的研究和关注。有机小分子光电材料因其结构明确、易于修饰、提纯加工简单等优点而被大量的用来开发作为高性能材料。目前来说，能够满足工业需求的发光光材料及主体材料仍然较少。菲并咪唑类化合物具有较大的刚性平面骨架﹑良好的热稳定性及较高的荧光量子效率，同时具有合成简单﹑产率高﹑提纯容易的特点，因此受到人们的广泛关注。In recent years, with the great application prospects in the fields of full-color display and solid-state white lighting, organic electroluminescent technology has received extensive research and attention in both scientific research circles and industrial circles. Organic small molecule optoelectronic materials have been widely used to develop high-performance materials because of their clear structure, easy modification, and simple purification and processing. At present, there are still few luminescent materials and host materials that can meet the needs of the industry. Phenanthroimidazole compounds have large rigid planar framework, good thermal stability and high fluorescence quantum efficiency, and have the characteristics of simple synthesis, high yield and easy purification, so they have attracted widespread attention.
发明内容Contents of the invention
本发明的目的在于提供一类新型的三苯乙烯基取代菲并咪唑衍生物聚集诱导发光材料及其在制备有机电致发光器件中的应用。The purpose of the present invention is to provide a new type of tristyryl-substituted phenanthroimidazole derivative aggregation-induced luminescent material and its application in the preparation of organic electroluminescent devices.
该类新型三苯乙烯基取代菲并咪唑衍生物的突出特点是将菲并咪唑基团和三苯乙烯基团通过一个苯环连接在一起，该类分子不仅继承了菲并咪唑良好的热稳定性、较高的电子迁移率和较高的荧光量子效率等优点，而且也继承了三苯乙烯基聚集诱导发光的性质，克服了聚集引起荧光淬灭问题。同时，分子具有较大的扭曲结构，能够保证化合物在固态时具有很高的荧光量子效率(40％以上)，利用该类材料作为发光层制备的有机电致发光器件具有优良的性能。The outstanding feature of this new type of tristyryl-substituted phenanthroimidazole derivatives is that the phenanthroimidazole group and the tristyryl group are linked together through a benzene ring. This type of molecule not only inherits the good thermal stability of phenanthroimidazole It also inherits the properties of tristyryl-based aggregation-induced luminescence, and overcomes the problem of fluorescence quenching caused by aggregation. At the same time, the molecule has a large twisted structure, which can ensure that the compound has a high fluorescence quantum efficiency (above 40%) in the solid state, and the organic electroluminescent device prepared by using this kind of material as the light-emitting layer has excellent performance.
本发明所涉及的化合物通式如下所示：The general formula of the compound involved in the present invention is as follows:
其中R1可以是H、F、CN、含有1～10个碳原子的直链或支链烷基、含有1～10个碳原子的直链或支链烷氧基、苯环等。Wherein R1 can be H, F, CN, a straight chain or branched chain alkyl group containing 1 to 10 carbon atoms, a straight chain or branched chain alkoxy group containing 1 to 10 carbon atoms, a benzene ring, etc.
R2和R3相同或不相同，可以是H、F、含有1～10个碳原子的直链或支链烷基、含有1～10个碳原子的直链或支链烷氧基、苯环等。 R2 and R3 are the same or different, and can be H, F, straight-chain or branched-chain alkyl containing 1-10 carbon atoms, straight-chain or branched-chain alkoxy containing 1-10 carbon atoms, benzene Ring etc.
Ar可以是含有1～6个碳原子的直链或支链烷基取代的苯环、含有1～6个碳原子的直链或支链烷氧基取代的苯环。Ar may be a straight chain or branched chain alkyl substituted benzene ring containing 1 to 6 carbon atoms, a straight chain or branched chain alkoxy substituted benzene ring containing 1 to 6 carbon atoms.
本发明所涉及的化合物合成路线如下所示：The synthetic routes of the compounds involved in the present invention are as follows:
本发明所涉及到的代表性菲并咪唑衍生物(1-36)其结构式如下所示：The structural formula of representative phenanthroimidazole derivatives (1-36) involved in the present invention is as follows:
附图说明Description of drawings
图1：应用本发明所述材料制备的有机电致发光器件结构示意图。Fig. 1: Schematic diagram of the structure of an organic electroluminescent device prepared by using the material of the present invention.
图2：应用本发明所述化合物9制备的有机电致发光器件光谱图。Fig. 2: Spectrum diagram of an organic electroluminescent device prepared by using compound 9 of the present invention.
图3：应用本发明所述材料32制备的有机电致发光器件光谱图。Fig. 3: Spectrum diagram of an organic electroluminescent device prepared by using the material 32 of the present invention.
本发明所述的有机电致发光器件由阴极、阳极和两电极之间的一层或多层有机层构成，有机层中至少一层为发光层，本发明所述的一种以上三苯乙烯基取代菲并咪唑衍生物的聚集诱导发光材料用于制备该发光层。The organic electroluminescent device of the present invention is composed of one or more organic layers between the cathode, the anode and the two electrodes, at least one of the organic layers is a light-emitting layer, and one or more triphenylethylenes described in the present invention The aggregation-induced luminescent material of substituted phenanthroimidazole derivatives is used to prepare the luminescent layer.
本发明制备的电致发光器件的结构如图1所示，各部件名称为：透明玻璃或其它透明衬底1、附着在透明衬底上的ITO(铟锡氧化物)阳极2、NPB(N，N'-二(1-萘基)-N，N'-二苯基-1，1'-联苯-4，4'-二胺)空穴传输层3、本发明所述材料制备的发光层4、间三(苯基苯并咪唑)苯(TPBI)电子传输层5、LiF电子注入层6、金属Al阴极7。The structure of the electroluminescent device prepared by the present invention is as shown in Figure 1, and each part name is: transparent glass or other transparent substrate 1, the ITO (indium tin oxide) anode 2 that is attached on the transparent substrate, NPB (N , N'-bis(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine) hole transport layer 3, prepared from the material of the present invention Light emitting layer 4 , m-tris(phenylbenzimidazole) benzene (TPBI) electron transport layer 5 , LiF electron injection layer 6 , metal Al cathode 7 .
本发明所述的有机电致发光器件可用于制备有机电致发光显示器或有机电致发光照明光源。The organic electroluminescent device described in the invention can be used to prepare organic electroluminescent displays or organic electroluminescent lighting sources.
NPB及TPBI结构式如下所示：The structural formulas of NPB and TPBI are as follows:
具体实施方式Detailed ways
实施例1：化合物1的合成：Embodiment 1: the synthesis of compound 1:
将菲醌(12mmol)，对溴苯甲醛(12mmol)，苯胺(32mmol)，乙酸铵(62.5mmol)，乙酸(50mL)加入三口瓶中，N2保护下，于油浴123℃加热回流12h。停止反应，将反应混合物倒入蒸馏水中，搅拌过滤，所得灰色滤饼依次用水，冰醋酸，乙醇洗涤，烘干后得到对位溴取代的菲并咪唑中间体(4.57g,产率85％)。将上述得到的对位溴取代菲并咪唑(0.90g,2mmol)，2-(4-(2,2-二苯乙烯基)苯基-4,4,5,5-四甲基-1,3,2-二氧杂戊硼烷(0.84g,2.2mmol)，碳酸钾(1.66g,12mmol)，四(三苯基磷)钯(23.1mg,0.02mmol)与20ml甲苯和6ml水混合加入圆底烧瓶中。脱气三次后氮气保护，在85℃下反应12小时。待反应混合物冷却后，使用二氯甲烷和水进行萃取，取有机相，用无水硫酸钠干燥。减压蒸馏，浓缩溶剂后经硅胶柱层析分析，展开剂为二氯甲烷，得到白色固体936mg，产率为75.0％。质谱分析确定的分子离子质量为：624.67(计算值为：624.26)；理论元素含量(％)C47H32N2：C，90.35；H，5.16；N，4.48，实测元素含量(％)：C，90.55；H，5.10；N，4.34。上述分析结果表明，获得的产物为预计的产品。Add phenanthrenequinone (12mmol), p-bromobenzaldehyde (12mmol), aniline (32mmol), ammonium acetate (62.5mmol), and acetic acid (50mL) into a three-necked flask, and heat to reflux in an oil bath at 123°C for 12h under the protection of N2 . The reaction was stopped, the reaction mixture was poured into distilled water, stirred and filtered, the gray filter cake obtained was washed with water, glacial acetic acid and ethanol successively, and after drying, the phenanthroimidazole intermediate (4.57g, yield 85%) obtained by para-bromine substituted . The para-bromo-substituted phenanthroimidazole obtained above (0.90g, 2mmol), 2-(4-(2,2-distyryl)phenyl-4,4,5,5-tetramethyl-1, 3,2-dioxaborolane (0.84g, 2.2mmol), potassium carbonate (1.66g, 12mmol), tetrakis (triphenylphosphine) palladium (23.1mg, 0.02mmol) mixed with 20ml of toluene and 6ml of water were added In a round bottom flask. After degassing three times, under nitrogen protection, react at 85 ° C for 12 hours. After the reaction mixture is cooled, use dichloromethane and water to extract, take the organic phase, and dry it with anhydrous sodium sulfate. Distillation under reduced pressure, After concentrating the solvent, through silica gel column chromatography analysis, developing agent is dichloromethane, obtains white solid 936mg, productive rate is 75.0%.The molecular ion mass that mass spectrometry determines is: 624.67 (calculated value: 624.26); Theoretical element content ( %) C 47 H 32 N 2 : C, 90.35; H, 5.16; N, 4.48, measured element content (%): C, 90.55; H, 5.10; The product.
实施例2：化合物2的合成：Embodiment 2: the synthesis of compound 2:
依照化合物1的合成，步骤相同，用对甲基苯胺代替苯胺，得到白色粉末状化合物2(1.05g，产率82％)，质谱分析确定的分子离子质量为：638.18(计算值为：638.27)；理论元素含量(％)C48H34N2：C，90.25；H，5.36；N，4.39；实测元素含量(％)：C，90.10；H，5.33；N，4.56。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, and p-methylaniline is used instead of aniline to obtain white powder compound 2 (1.05g, yield 82%). The molecular ion mass determined by mass spectrometry is: 638.18 (calculated value: 638.27) ; Theoretical element content (%) C 48 H 34 N 2 : C, 90.25; H, 5.36; N, 4.39; Measured element content (%): C, 90.10; H, 5.33; N, 4.56. The above analysis results indicated that the obtained product was the expected product.
实施例3：化合物3的合成：Embodiment 3: the synthesis of compound 3:
依照化合物1的合成，步骤相同，用对叔丁基苯胺代替苯胺，得到白色粉末状化合物3(1.06g，产率78％)，质谱分析确定的分子离子质量为：680.55(计算值为：680.32)；理论元素含量(％)C51H40N2：C，89.96；H，5.92；N，4.11；实测元素含量(％)：C，90.02；H，5.80；N，4.17。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, and aniline is replaced by p-tert-butylaniline to obtain white powder compound 3 (1.06g, yield 78%), and the molecular ion mass determined by mass spectrometry is: 680.55 (calculated value: 680.32 ); theoretical element content (%) C 51 H 40 N 2 : C, 89.96; H, 5.92; N, 4.11; measured element content (%): C, 90.02; H, 5.80; N, 4.17. The above analysis results indicated that the obtained product was the expected product.
实施例4：化合物4的合成：Embodiment 4: the synthesis of compound 4:
依照化合物1的合成，步骤相同，用对甲氧基苯胺代替苯胺，得到白色粉末状化合物4(1.05g，产率80％)，质谱分析确定的分子离子质量为：654.35(计算值为：654.27)；理论元素含量(％)C48H34N2O：C，88.04；H，5.23；N，4.28；实测元素含量(％)：C，88.12；H，5.08；N，4.22。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, and p-methoxyaniline is used instead of aniline to obtain white powder compound 4 (1.05g, yield 80%), and the molecular ion mass determined by mass spectrometry is: 654.35 (calculated value: 654.27 ); theoretical element content (%) C 48 H 34 N 2 O: C, 88.04; H, 5.23; N, 4.28; measured element content (%): C, 88.12; H, 5.08; N, 4.22. The above analysis results indicated that the obtained product was the expected product.
实施例5：化合物5的合成：Embodiment 5: the synthesis of compound 5:
依照化合物1的合成，步骤相同，用对氰基苯胺代替苯胺，得到白色粉末状化合物5(0.99g，产率76％)，质谱分析确定的分子离子质量为：649.42(计算值为：649.25)；理论元素含量(％)C48H31N3：C，88.72；H，4.81；N，6.47；实测元素含量(％)：C，88.48；H，4.95；N，6.56。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, and p-cyanoaniline is used instead of aniline to obtain white powder compound 5 (0.99g, yield 76%), and the molecular ion mass determined by mass spectrometry is: 649.42 (calculated value: 649.25) ; Theoretical element content (%) C 48 H 31 N 3 : C, 88.72; H, 4.81; N, 6.47; Measured element content (%): C, 88.48; H, 4.95; N, 6.56. The above analysis results indicated that the obtained product was the expected product.
实施例6：化合物6的合成：Embodiment 6: the synthesis of compound 6:
依照化合物1的合成，步骤相同，用3-甲基苯胺代替苯胺，得到白色粉末状化合物6(0.97g，产率76％)，质谱分析确定的分子离子质量为：638.33(计算值为：638.27)；理论元素含量(％)C48H34N2：C，90.25；H，5.36；N，4.39；实测元素含量(％)：C，90.15；H，5.30；N，4.55。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, and 3-methylaniline is used instead of aniline to obtain white powder compound 6 (0.97g, yield 76%), and the molecular ion mass determined by mass spectrometry is: 638.33 (calculated value: 638.27 ); theoretical element content (%) C 48 H 34 N 2 : C, 90.25; H, 5.36; N, 4.39; measured element content (%): C, 90.15; H, 5.30; N, 4.55. The above analysis results indicated that the obtained product was the expected product.
实施例7：化合物7的合：Embodiment 7: the synthesis of compound 7:
依照化合物1的合成，步骤相同，用对叔丁基苯胺代替苯胺，得到白色粉末状化合物7(0.99g，产率73％)，质谱分析确定的分子离子质量为：680.46(计算值为：680.32)；理论元素含量(％)C51H40N2：C，89.96；H，5.92；N，4.11；实测元素含量(％)：C，89.76；H，5.99；N，4.24。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, and p-tert-butylaniline is used instead of aniline to obtain white powder compound 7 (0.99g, yield 73%), and the molecular ion mass determined by mass spectrometry is: 680.46 (calculated value: 680.32 ); theoretical element content (%) C 51 H 40 N 2 : C, 89.96; H, 5.92; N, 4.11; measured element content (%): C, 89.76; H, 5.99; N, 4.24. The above analysis results indicated that the obtained product was the expected product.
实施例8：化合物8的合成：Embodiment 8: the synthesis of compound 8:
依照化合物1的合成，步骤相同，用对甲氧基苯胺代替苯胺，得到白色粉末状化合物8(0.94g，产率72％)，质谱分析确定的分子离子质量为：654.39(计算值为：654.27)；理论元素含量(％)C48H34N2O：C，88.04；H，5.23；N，4.28；实测元素含量(％)：C，87.94；H，5.18；N，4.38。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, and p-methoxyaniline is used instead of aniline to obtain white powder compound 8 (0.94g, yield 72%), and the molecular ion mass determined by mass spectrometry is: 654.39 (calculated value: 654.27 ); theoretical element content (%) C 48 H 34 N 2 O: C, 88.04; H, 5.23; N, 4.28; measured element content (%): C, 87.94; H, 5.18; N, 4.38. The above analysis results indicated that the obtained product was the expected product.
实施例9：化合物9的合成：Embodiment 9: the synthesis of compound 9:
依照化合物1的合成，步骤相同，用间溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物9(1.06g，产率85％)，质谱分析确定的分子离子质量为：624.48(计算值为：624.26)；理论元素含量(％)C47H32N2：C，90.35；H，5.16；N，4.48；实测元素含量(％)：C，90.10；H，5.21；N，4.68。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, replace p-bromobenzaldehyde with m-bromobenzaldehyde, obtain white powder compound 9 (1.06g, yield 85%), the molecular ion mass determined by mass spectrometry is: 624.48 (the calculated value is : 624.26); theoretical element content (%) C 47 H 32 N 2 : C, 90.35; H, 5.16; N, 4.48; measured element content (%): C, 90.10; H, 5.21; N, 4.68. The above analysis results indicated that the obtained product was the expected product.
实施例10：化合物10的合成：Embodiment 10: the synthesis of compound 10:
依照化合物1的合成，步骤相同，用对甲基苯胺代替苯胺，间溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物10(0.89g，产率70％)，质谱分析确定的分子离子质量为：638.50(计算值为：638.27)；理论元素含量(％)C48H34N2：C，90.25；H，5.36；N，4.39；实测元素含量(％)：C，90.36；H，5.29；N，4.34。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, with p-methylaniline instead of aniline, m-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 10 (0.89g, yield 70%), the molecular ion mass determined by mass spectrometry For: 638.50 (calculated value: 638.27); theoretical element content (%) C 48 H 34 N 2 : C, 90.25; H, 5.36; N, 4.39; measured element content (%): C, 90.36; H, 5.29 ; N, 4.34. The above analysis results indicated that the obtained product was the expected product.
实施例11：化合物11的合成：Embodiment 11: the synthesis of compound 11:
依照化合物1的合成，步骤相同，用对叔丁基苯胺代替苯胺，间溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物11(0.94g，产率69％)，质谱分析确定的分子离子质量为：680.47(计算值为：680.32)；理论元素含量(％)C51H40N2：C，89.96；H，5.92；N，4.11；实测元素含量(％)：C，90.11；H，5.87；N，4.02。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, replacing aniline with p-tert-butylaniline, and m-bromobenzaldehyde instead of p-bromobenzaldehyde to obtain white powder compound 11 (0.94g, yield 69%), and the molecular ion determined by mass spectrometry Mass: 680.47 (calculated value: 680.32); theoretical element content (%) C 51 H 40 N 2 : C, 89.96; H, 5.92; N, 4.11; measured element content (%): C, 90.11; H, 5.87; N, 4.02. The above analysis results indicated that the obtained product was the expected product.
实施例12：化合物12的合成：Embodiment 12: the synthesis of compound 12:
依照化合物1的合成，步骤相同，用对甲氧基苯胺代替苯胺，间溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物12(0.89g，产率68％)，质谱分析确定的分子离子质量为：654.36(计算值为：654.27)；理论元素含量(％)C48H34N2O：C，88.04；H，5.23；N，4.28；实测元素含量(％)：C，88.15；H，5.27；N，4.20。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, with p-methoxyaniline instead of aniline, m-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 12 (0.89g, yield 68%), the molecular ion determined by mass spectrometry Mass: 654.36 (calculated value: 654.27); theoretical element content (%) C 48 H 34 N 2 O: C, 88.04; H, 5.23; N, 4.28; measured element content (%): C, 88.15; H , 5.27; N, 4.20. The above analysis results indicated that the obtained product was the expected product.
实施例13：化合物13的合成：Embodiment 13: the synthesis of compound 13:
依照化合物1的合成，步骤相同，用对氰基苯胺代替苯胺，间溴苯甲醛代替对溴苯甲醛,得到白色粉末状化合物13(0.84g，产率65％)，质谱分析确定的分子离子质量为：649.36(计算值为：649.25)；理论元素含量(％)C48H31N3：C，88.72；H，4.81；N，6.47；实测元素含量(％)：C，88.50；H，4.90；N，6.60。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, with p-cyanoaniline instead of aniline, m-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 13 (0.84g, yield 65%), the molecular ion mass determined by mass spectrometry For: 649.36 (calculated value: 649.25); theoretical element content (%) C 48 H 31 N 3 : C, 88.72; H, 4.81; N, 6.47; measured element content (%): C, 88.50; H, 4.90 ; N, 6.60. The above analysis results indicated that the obtained product was the expected product.
实施例14：化合物14的合成：Embodiment 14: the synthesis of compound 14:
依照化合物1的合成，步骤相同，用3-甲基苯胺代替苯胺，间溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物14(0.83g，产率65％)，质谱分析确定的分子离子质量为：638.49(计算值为：638.27)；理论元素含量(％)C48H34N2：C，90.25；H，5.36；N，4.39；实测元素含量(％)：C，90.15；H，5.39；N，4.45。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, with 3-methylaniline instead of aniline, m-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 14 (0.83g, yield 65%), and the molecular ion determined by mass spectrometry analysis Mass: 638.49 (calculated value: 638.27); theoretical element content (%) C 48 H 34 N 2 : C, 90.25; H, 5.36; N, 4.39; measured element content (%): C, 90.15; H, 5.39; N, 4.45. The above analysis results indicated that the obtained product was the expected product.
实施例15：化合物15的合成：Embodiment 15: the synthesis of compound 15:
依照化合物1的合成，步骤相同，用3-叔丁基苯胺代替苯胺，间溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物15(0.84g，产率62％)，质谱分析确定的分子离子质量为：680.51(计算值为：680.32)；理论元素含量(％)C51H40N2：C，89.96；H，5.92；N，4.11；实测元素含量(％)：C，90.06；H，5.97；N，3.96。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, with 3-tert-butylaniline instead of aniline, and m-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 15 (0.84g, yield 62%), the molecule determined by mass spectrometry Ion mass: 680.51 (calculated value: 680.32); theoretical element content (%) C 51 H 40 N 2 : C, 89.96; H, 5.92; N, 4.11; measured element content (%): C, 90.06; H , 5.97; N, 3.96. The above analysis results indicated that the obtained product was the expected product.
实施例16：化合物16的合成：Embodiment 16: the synthesis of compound 16:
依照化合物1的合成，步骤相同，用3-甲氧基苯胺代替苯胺，间溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物16(0.81g，产率62％)，质谱分析确定的分子离子质量为：654.40(计算值为：654.27)；理论元素含量(％)C48H34N2O：C，88.04；H，5.23；N，4.28；实测元素含量(％)：C，88.21；H，5.20；N，4.22。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, with 3-methoxyaniline instead of aniline, and m-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 16 (0.81g, yield 62%), the molecule determined by mass spectrometry analysis Ion mass: 654.40 (calculated value: 654.27); theoretical element content (%) C 48 H 34 N 2 O: C, 88.04; H, 5.23; N, 4.28; measured element content (%): C, 88.21; H, 5.20; N, 4.22. The above analysis results indicated that the obtained product was the expected product.
实施例17：化合物17的合成：Embodiment 17: the synthesis of compound 17:
依照化合物1的合成，步骤相同，用2-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物17(0.94g，产率75％)，质谱分析确定的分子离子质量为：624.53(计算值为：624.26)；理论元素含量(％)C47H32N2：C，90.35；H，5.16；N，4.48；实测元素含量(％)：C，90.51；H，5.10；N，4.38。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, and 2-bromobenzaldehyde is used instead of p-bromobenzaldehyde to obtain white powder compound 17 (0.94g, yield 75%), and the molecular ion mass determined by mass spectrometry is: 624.53 (calculated value is: 624.26); theoretical element content (%) C 47 H 32 N 2 : C, 90.35; H, 5.16; N, 4.48; measured element content (%): C, 90.51; H, 5.10; N, 4.38. The above analysis results indicated that the obtained product was the expected product.
实施例18：化合物18的合成：Embodiment 18: the synthesis of compound 18:
依照化合物1的合成，步骤相同，用对甲基苯胺代替苯胺，2-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物18(0.80g，产率63％)，质谱分析确定的分子离子质量为：638.39(计算值为：638.27)；理论元素含量(％)C48H34N2：C，90.25；H，5.36；N，4.39；实测元素含量(％)：C，90.38；H，5.31；N，4.30。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, with p-methylaniline instead of aniline, 2-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 18 (0.80g, yield 63%), the molecular ion determined by mass spectrometry Mass: 638.39 (calculated value: 638.27); theoretical element content (%) C 48 H 34 N 2 : C, 90.25; H, 5.36; N, 4.39; measured element content (%): C, 90.38; H, 5.31; N, 4.30. The above analysis results indicated that the obtained product was the expected product.
实施例19：化合物19的合成：Embodiment 19: the synthesis of compound 19:
依照化合物1的合成，步骤相同，用对叔丁基苯胺代替苯胺，2-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物19(0.79g，产率58％)，质谱分析确定的分子离子质量为：680.48(计算值为：680.32)；理论元素含量(％)C51H40N2：C，89.96；H，5.92；N，4.11；实测元素含量(％)：C，90.09；H，5.86；N，4.04。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, with p-tert-butylaniline instead of aniline, and 2-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 19 (0.79g, yield 58%), the molecule determined by mass spectrometry Ion mass: 680.48 (calculated value: 680.32); theoretical element content (%) C 51 H 40 N 2 : C, 89.96; H, 5.92; N, 4.11; measured element content (%): C, 90.09; H , 5.86; N, 4.04. The above analysis results indicated that the obtained product was the expected product.
实施例20：化合物20的合成：Embodiment 20: the synthesis of compound 20:
依照化合物1的合成，步骤相同，用对甲氧基苯胺代替苯胺，2-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物20(0.75g，产率57％)，质谱分析确定的分子离子质量为：654.55(计算值为：654.27)；理论元素含量(％)C48H34N2O：C，88.04；H，5.23；N，4.28；实测元素含量(％)：C，88.18；H，5.19；N，4.16。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, with p-methoxyaniline instead of aniline, and 2-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 20 (0.75g, yield 57%), the molecule determined by mass spectrometry Ion mass: 654.55 (calculated value: 654.27); theoretical element content (%) C 48 H 34 N 2 O: C, 88.04; H, 5.23; N, 4.28; measured element content (%): C, 88.18; H, 5.19; N, 4.16. The above analysis results indicated that the obtained product was the expected product.
实施例21：化合物21的合成：Embodiment 21: the synthesis of compound 21:
依照化合物1的合成，步骤相同，用对氰基苯胺代替苯胺，2-溴苯甲醛代替对溴苯甲醛,得到白色粉末状化合物21(0.77g，产率59％)，质谱分析确定的分子离子质量为：649.41(计算值为：649.25)；理论元素含量(％)C48H31N3：C，88.72；H，4.81；N，6.47；实测元素含量(％)：C，88.85；H，4.76；N，6.38。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, with p-cyanoaniline instead of aniline, 2-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 21 (0.77g, yield 59%), the molecular ion determined by mass spectrometry Mass: 649.41 (calculated value: 649.25); theoretical element content (%) C 48 H 31 N 3 : C, 88.72; H, 4.81; N, 6.47; measured element content (%): C, 88.85; H, 4.76; N, 6.38. The above analysis results indicated that the obtained product was the expected product.
实施例22：化合物22的合成：Embodiment 22: the synthesis of compound 22:
依照化合物1的合成，步骤相同，用对甲基苯胺代替苯胺，2-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物22(0.71g，产率56％)，质谱分析确定的分子离子质量为：638.53(计算值为：638.27)；理论元素含量(％)C48H34N2：C，90.25；H，5.36；N，4.39；实测元素含量(％)：C，90.11；H，5.41；N，4.47。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, replace aniline with p-methylaniline, and replace p-bromobenzaldehyde with 2-bromobenzaldehyde to obtain white powder compound 22 (0.71g, yield 56%), and the molecular ion determined by mass spectrometry analysis Mass: 638.53 (calculated value: 638.27); theoretical element content (%) C 48 H 34 N 2 : C, 90.25; H, 5.36; N, 4.39; measured element content (%): C, 90.11; H, 5.41; N, 4.47. The above analysis results indicated that the obtained product was the expected product.
实施例23：化合物23的合成：Embodiment 23: the synthesis of compound 23:
依照化合物1的合成，步骤相同，用3-叔丁基苯胺代替苯胺，2-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物23(0.72g，产率53％)，质谱分析确定的分子离子质量为：680.45(计算值为：680.32)；理论元素含量(％)C51H40N2：C，89.96；H，5.92；N，4.11；实测元素含量(％)：C，89.90；H，5.89；N，4.21。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, with 3-tert-butylaniline instead of aniline, 2-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 23 (0.72g, yield 53%), mass spectrometry determined Molecular ion mass: 680.45 (calculated value: 680.32); theoretical element content (%) C 51 H 40 N 2 : C, 89.96; H, 5.92; N, 4.11; measured element content (%): C, 89.90; H, 5.89; N, 4.21. The above analysis results indicated that the obtained product was the expected product.
实施例24：化合物24的合成：Embodiment 24: the synthesis of compound 24:
依照化合物1的合成，步骤相同，用3-甲氧基苯胺代替苯胺，2-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物24(0.65g，产率50％)，质谱分析确定的分子离子质量为：654.48(计算值为：654.27)；理论元素含量(％)C48H34N2O：C，88.04；H，5.23；N，4.28；实测元素含量(％)：C，87.98；H，5.19；N，4.44。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, with 3-methoxyaniline instead of aniline, 2-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 24 (0.65g, yield 50%), mass spectrometry determined Molecular ion mass: 654.48 (calculated value: 654.27); theoretical element content (%) C 48 H 34 N 2 O: C, 88.04; H, 5.23; N, 4.28; measured element content (%): C, 87.98 ; H, 5.19; N, 4.44. The above analysis results indicated that the obtained product was the expected product.
实施例25：化合物25的合成：Embodiment 25: the synthesis of compound 25:
依照化合物1的合成，步骤相同，用2,7-二苯基菲醌代替菲醌，得到白色粉末状化合物25(0.71g，产率46％)，质谱分析确定的分子离子质量为：776.46(计算值为：776.32)；理论元素含量(％)C59H40N2：C，91.21；H，5.19；N，3.61；实测元素含量(％)：C，91.15；H，5.12；N，3.72。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, and 2,7-diphenylphenanthrenequinone is used instead of phenanthrenequinone to obtain white powder compound 25 (0.71g, yield 46%), and the molecular ion mass determined by mass spectrometry is: 776.46 ( Calculated value: 776.32); theoretical element content (%) C 59 H 40 N 2 : C, 91.21; H, 5.19; N, 3.61; measured element content (%): C, 91.15; H, 5.12; N, 3.72 . The above analysis results indicated that the obtained product was the expected product.
实施例26：化合物26的合成：Embodiment 26: the synthesis of compound 26:
依照化合物1的合成，步骤相同，用2,7-二苯基菲醌代替菲醌，3-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物26(0.65g，产率42％)，质谱分析确定的分子离子质量为：776.51(计算值为：776.32)；理论元素含量(％)C59H40N2：C，91.21；H，5.19；N，3.61；实测元素含量(％)：C，91.32；H，5.15；N，3.53。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps were the same, and 2,7-diphenylphenanthrenequinone was used instead of phenanthrenequinone, and 3-bromobenzaldehyde was used instead of p-bromobenzaldehyde to obtain white powder compound 26 (0.65g, yield 42%). The molecular ion mass determined by mass spectrometry is: 776.51 (calculated value: 776.32); theoretical element content (%) C 59 H 40 N 2 : C, 91.21; H, 5.19; N, 3.61; measured element content (%): C, 91.32; H, 5.15; N, 3.53. The above analysis results indicated that the obtained product was the expected product.
实施例27：化合物27的合成：Embodiment 27: the synthesis of compound 27:
依照化合物1的合成，步骤相同，用2,7-二苯基菲醌代替菲醌，2-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物27(0.65g，产率42％)，质谱分析确定的分子离子质量为：776.58(计算值为：776.32)；理论元素含量(％)C59H40N2：C，91.21；H，5.19；N，3.61；实测元素含量(％)：C，91.18；H，5.32；N，3.50。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps were the same, and 2,7-diphenylphenanthrenequinone was used instead of phenanthrenequinone, and 2-bromobenzaldehyde was used instead of p-bromobenzaldehyde to obtain white powder compound 27 (0.65g, yield 42%). The molecular ion mass determined by mass spectrometry is: 776.58 (calculated value: 776.32); theoretical element content (%) C 59 H 40 N 2 : C, 91.21; H, 5.19; N, 3.61; measured element content (%): C, 91.18; H, 5.32; N, 3.50. The above analysis results indicated that the obtained product was the expected product.
实施例28：化合物28的合成：Embodiment 28: the synthesis of compound 28:
依照化合物1的合成，步骤相同，用3,6-二苯基菲醌代替菲醌，得到白色粉末状化合物28(0.79g，产率51％)，质谱分析确定的分子离子质量为：776.52(计算值为：776.32)；理论元素含量(％)C59H40N2：C，91.21；H，5.19；N，3.61；实测元素含量(％)：C，91.31；H，5.22；N，3.46。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps are the same, and 3,6-diphenylphenanthrenequinone is used instead of phenanthrenequinone to obtain white powder compound 28 (0.79g, yield 51%), and the molecular ion mass determined by mass spectrometry is: 776.52( Calculated value: 776.32); theoretical element content (%) C 59 H 40 N 2 : C, 91.21; H, 5.19; N, 3.61; measured element content (%): C, 91.31; H, 5.22; N, 3.46 . The above analysis results indicated that the obtained product was the expected product.
实施例29：化合物29的合成：Embodiment 29: the synthesis of compound 29:
依照化合物1的合成，步骤相同，用3,6-二苯基菲醌代替菲醌，3-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物29(0.65g，产率42％)，质谱分析确定的分子离子质量为：776.56(计算值为：776.32)；理论元素含量(％)C59H40N2：C，91.21；H，5.19；N，3.61；实测元素含量(％)：C，91.25；H，5.23；N，3.50。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps were the same, and 3,6-diphenylphenanthrenequinone was used instead of phenanthrenequinone, and 3-bromobenzaldehyde was used instead of p-bromobenzaldehyde to obtain white powder compound 29 (0.65 g, yield 42%). The molecular ion mass determined by mass spectrometry is: 776.56 (calculated value: 776.32); theoretical element content (%) C 59 H 40 N 2 : C, 91.21; H, 5.19; N, 3.61; measured element content (%): C, 91.25; H, 5.23; N, 3.50. The above analysis results indicated that the obtained product was the expected product.
实施例30：化合物30的合成：Embodiment 30: the synthesis of compound 30:
依照化合物1的合成，步骤相同，用3,6-二苯基菲醌代替菲醌，3-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物30(0.76g，产率49％)，质谱分析确定的分子离子质量为：776.42(计算值为：776.32)；理论元素含量(％)C59H40N2：C，91.21；H，5.19；N，3.61；实测元素含量(％)：C，91.15；H，5.33；N，3.52。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 1, the steps were the same, and 3,6-diphenylphenanthrenequinone was used instead of phenanthrenequinone, and 3-bromobenzaldehyde was used instead of p-bromobenzaldehyde to obtain white powder compound 30 (0.76g, yield 49%). The molecular ion mass determined by mass spectrometry is: 776.42 (calculated value: 776.32); theoretical element content (%) C 59 H 40 N 2 : C, 91.21; H, 5.19; N, 3.61; measured element content (%): C, 91.15; H, 5.33; N, 3.52. The above analysis results indicated that the obtained product was the expected product.
实施例31：化合物31的合成：Example 31: Synthesis of Compound 31:
将菲醌(2.52g,12mmol)，对硝基苯甲醛(1.81g,12mmol)，苯胺(2.98g,32mmol)，乙酸铵(4.81g,62.5mmol)，乙酸(50mL)加入三口瓶中，N2保护下，于油浴123℃加热回流12h.停止反应，将反应混合物倒入蒸馏水中，搅拌过滤，所得灰色滤饼依次用水，冰醋酸，乙醇洗涤，烘干后得到灰白色粉末，然后用柱层析方法分离(硅胶，二氯甲烷)得白色粉末状产物4H-NO2(4.58g,产率92％)。The phenanthrenequinone (2.52g, 12mmol), p-nitrobenzaldehyde (1.81g, 12mmol), aniline (2.98g, 32mmol), ammonium acetate (4.81g, 62.5mmol), acetic acid (50mL) was added in the there-necked flask, N Under the protection of 2 , heat and reflux in an oil bath at 123°C for 12 hours. Stop the reaction, pour the reaction mixture into distilled water, stir and filter, and the gray filter cake obtained is washed with water, glacial acetic acid, and ethanol in sequence, and after drying, an off-white powder is obtained. Chromatographic separation (silica gel, dichloromethane) gave the product 4H-NO 2 as white powder (4.58 g, yield 92%).
将4H-NO2(0.93g,2mmol)，80％水合肼(0.13mg,2mmol)，10％Pd/C(0.02mmol)，乙醇(30mL)加入三口瓶中，N2保护下，于油浴80℃加热回流12h。停止反应，将反应混合物过滤，二氯甲烷洗涤滤饼，滤液旋干，得白色粉末状目标产物4H-NH2(0.73g,产率95％)。将菲醌(0.42g，2mmol)，对溴苯甲醛(0.37g，2mmol)，化合物4H-NH2(0.77g，2mmol)，乙酸铵(0.39g，5mmol)，乙酸(10mL)加入三口瓶中，N2保护下，于油浴123℃加热回流12h停止反应，将反应混合物倒入蒸馏水中，搅拌过滤，所得灰色滤饼依次用水、冰醋酸、乙醇洗涤，烘干后得到灰白色粉末，然后用柱层析方法分离(硅胶，二氯甲烷)得白色粉末状对位溴代双菲并咪唑中间体(1.11g，产率75％)。Add 4H-NO 2 (0.93g, 2mmol), 80% hydrazine hydrate (0.13mg, 2mmol), 10% Pd/C (0.02mmol), ethanol (30mL) into a three-necked flask, under N 2 protection, in an oil bath Heated to reflux at 80°C for 12h. The reaction was stopped, the reaction mixture was filtered, the filter cake was washed with dichloromethane, and the filtrate was spin-dried to obtain the target product 4H-NH 2 (0.73 g, yield 95%) in the form of white powder. Add phenanthrenequinone (0.42g, 2mmol), p-bromobenzaldehyde (0.37g, 2mmol), compound 4H-NH 2 (0.77g, 2mmol), ammonium acetate (0.39g, 5mmol), and acetic acid (10mL) into a three-necked flask , under the protection of N 2 , heated and refluxed in an oil bath at 123°C for 12 hours to stop the reaction, poured the reaction mixture into distilled water, stirred and filtered, the obtained gray filter cake was washed with water, glacial acetic acid, and ethanol in sequence, and after drying, an off-white powder was obtained, and then used Separation by column chromatography (silica gel, dichloromethane) gave the p-bromobis-phenanthroimidazole intermediate (1.11 g, yield 75%) in the form of white powder.
将上述得到的对位溴取代双菲并咪唑中间体(1.48g,2mmol)，2-(4-(2,2-二苯乙烯基)苯基-4,4,5,5-四甲基-1,3,2-二氧杂戊硼烷(0.84g,2.2mmol),碳酸钾(1.66g,12mmol),四(三苯基磷)钯(23.1mg,0.02mmol)与20ml甲苯和6ml水混合加入圆底烧瓶中。脱气三次后氮气保护,在85℃下反应12小时。待反应混合物冷却后，使用二氯甲烷和水进行萃取，取有机相，用无水硫酸钠干燥。减压蒸馏，浓缩溶剂后经硅胶柱层析分析，展开剂为二氯甲烷，得到白色固体1.40g，产率为75.0％。质谱分析确定的分子离子质量为：916.45(计算值为：916.36)；理论元素含量(％)C68H44N4：C，89.06；H，4.84；N，6.11；实测元素含量(％)：C，89.23；H，4.74；N，6.02。上述分析结果表明，获得的产物为预计的产品。The p-bromo-substituted bis-phenanthroimidazole intermediate obtained above (1.48g, 2mmol), 2-(4-(2,2-distyryl)phenyl-4,4,5,5-tetramethyl -1,3,2-dioxaborolane (0.84g, 2.2mmol), potassium carbonate (1.66g, 12mmol), tetrakis (triphenylphosphine) palladium (23.1mg, 0.02mmol) with 20ml of toluene and 6ml Water was mixed and added to a round-bottomed flask. After degassing three times, nitrogen was protected and reacted at 85°C for 12 hours. After the reaction mixture was cooled, it was extracted with dichloromethane and water, and the organic phase was taken and dried with anhydrous sodium sulfate. Pressure distillation, after concentrating the solvent, analyze through silica gel column chromatography, developing agent is dichloromethane, obtains white solid 1.40g, productive rate is 75.0%.The molecular ion mass that mass spectrometry determines is: 916.45 (calculated value: 916.36); Theoretical element content (%) C 68 H 44 N 4 : C, 89.06; H, 4.84; N, 6.11; Measured element content (%): C, 89.23; H, 4.74; The product of is the expected product.
实施例32：化合物32的合成：Example 32: Synthesis of Compound 32:
依照化合物31的合成，步骤相同，用3-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物32(1.43g，产率78％)，质谱分析确定的分子离子质量为：916.51(计算值为：916.36)；理论元素含量(％)C68H44N4：C，89.06；H，4.84；N，6.11；实测元素含量(％)：C，89.11；H，4.88；N，6.01。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, and 3-bromobenzaldehyde is used instead of p-bromobenzaldehyde to obtain white powder compound 32 (1.43g, yield 78%), and the molecular ion mass determined by mass spectrometry is: 916.51 (calculated value is: 916.36); theoretical element content (%) C 68 H 44 N 4 : C, 89.06; H, 4.84; N, 6.11; measured element content (%): C, 89.11; H, 4.88; N, 6.01. The above analysis results indicated that the obtained product was the expected product.
实施例33：化合物33的合成：Example 33: Synthesis of Compound 33:
依照化合物31的合成，步骤相同，用2-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物33(1.28g，产率70％)，质谱分析确定的分子离子质量为：916.42(计算值为：916.36)；理论元素含量(％)C68H44N4：C，89.06；H，4.84；N，6.11；实测元素含量(％)：C，89.09；H，4.70；N，6.20。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, and 2-bromobenzaldehyde is used instead of p-bromobenzaldehyde to obtain white powder compound 33 (1.28g, yield 70%), and the molecular ion mass determined by mass spectrometry is: 916.42 (calculated value is: 916.36); theoretical element content (%) C 68 H 44 N 4 : C, 89.06; H, 4.84; N, 6.11; measured element content (%): C, 89.09; H, 4.70; N, 6.20. The above analysis results indicated that the obtained product was the expected product.
实施例34：化合物34的合成：Example 34: Synthesis of Compound 34:
依照化合物31的合成，步骤相同，用4-甲基苯胺代替苯胺，得到白色粉末状化合物34(1.40g，产率75％)，质谱分析确定的分子离子质量为：930.55(计算值为：930.37)；理论元素含量(％)C69H46N4：C，89.00；H，4.98；N，6.02；实测元素含量(％)：C，89.11；H，4.92；N，5.96。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, and 4-methylaniline is used instead of aniline to obtain white powder compound 34 (1.40 g, yield 75%). The molecular ion mass determined by mass spectrometry is: 930.55 (calculated value: 930.37 ); theoretical element content (%) C 69 H 46 N 4 : C, 89.00; H, 4.98; N, 6.02; measured element content (%): C, 89.11; H, 4.92; N, 5.96. The above analysis results indicated that the obtained product was the expected product.
实施例35：化合物35的合成：Example 35: Synthesis of Compound 35:
依照化合物31的合成，步骤相同，用4-叔丁基苯胺代替苯胺，得到白色粉末状化合物35(1.34g，产率69％)，质谱分析确定的分子离子质量为：972.61(计算值为：972.42)；理论元素含量(％)C72H52N4：C，88.86；H，5.39；N，5.76；实测元素含量(％)：C，89.01；H，5.30；N，5.68。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, and aniline is replaced with 4-tert-butylaniline to obtain white powder compound 35 (1.34g, yield 69%), and the molecular ion mass determined by mass spectrometry is: 972.61 (the calculated value is: 972.42); theoretical element content (%) C 72 H 52 N 4 : C, 88.86; H, 5.39; N, 5.76; measured element content (%): C, 89.01; H, 5.30; N, 5.68. The above analysis results indicated that the obtained product was the expected product.
实施例36：化合物36的合成：Example 36: Synthesis of compound 36:
依照化合物31的合成，步骤相同，用4-甲氧基苯胺代替苯胺，得到白色粉末状化合物36(1.34g，产率71％)，质谱分析确定的分子离子质量为：946.48(计算值为：946.37)；理论元素含量(％)C69H46N4O：C，87.50；H，4.90；N，5.92；实测元素含量(％)：C，87.45；H，4.98；N，5.86。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, and aniline is replaced with 4-methoxyaniline to obtain white powder compound 36 (1.34g, yield 71%), and the molecular ion mass determined by mass spectrometry is: 946.48 (the calculated value is: 946.37); theoretical element content (%) C 69 H 46 N 4 O: C, 87.50; H, 4.90; N, 5.92; measured element content (%): C, 87.45; H, 4.98; N, 5.86. The above analysis results indicated that the obtained product was the expected product.
实施例37：化合物37的合成：Example 37: Synthesis of Compound 37:
依照化合物31的合成，步骤相同，用4-氰基苯胺代替苯胺，得到白色粉末状化合物37(1.22g，产率65％)，质谱分析确定的分子离子质量为：941.52(计算值为：941.35)；理论元素含量(％)C69H43N5：C，87.97；H，4.60；N，7.43；实测元素含量(％)：C，87.93；H，4.52；N，7.54。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, and 4-cyanoaniline is used instead of aniline to obtain white powder compound 37 (1.22 g, yield 65%). The molecular ion mass determined by mass spectrometry is: 941.52 (calculated value: 941.35 ); theoretical element content (%) C 69 H 43 N 5 : C, 87.97; H, 4.60; N, 7.43; measured element content (%): C, 87.93; H, 4.52; N, 7.54. The above analysis results indicated that the obtained product was the expected product.
实施例38：化合物38的合成：Example 38: Synthesis of Compound 38:
依照化合物31的合成，步骤相同，用4-甲基苯胺代替苯胺，3-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物38(1.34g，产率72％)，质谱分析确定的分子离子质量为：930.51(计算值为：930.37)；理论元素含量(％)C69H46N4：C，89.00；H，4.98；N，6.02；实测元素含量(％)：C，88.96；H，4.94；N，6.10。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, with 4-methylaniline instead of aniline, and 3-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 38 (1.34g, yield 72%), the molecule determined by mass spectrometry Ion mass: 930.51 (calculated value: 930.37); theoretical element content (%) C 69 H 46 N 4 : C, 89.00; H, 4.98; N, 6.02; measured element content (%): C, 88.96; H , 4.94; N, 6.10. The above analysis results indicated that the obtained product was the expected product.
实施例39：化合物39的合成：Example 39: Synthesis of Compound 39:
依照化合物31的合成，步骤相同，用4-叔丁基苯胺代替苯胺，3-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物39(1.34g，产率69％)，质谱分析确定的分子离子质量为：972.65(计算值为：972.42)；理论元素含量(％)C72H52N4：C，88.86；H，5.39；N，5.76；实测元素含量(％)：C，88.81；H，5.50；N，5.68。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, with 4-tert-butylaniline instead of aniline, and 3-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 39 (1.34 g, yield 69%), which was determined by mass spectrometry. Molecular ion mass: 972.65 (calculated value: 972.42); theoretical element content (%) C 72 H 52 N 4 : C, 88.86; H, 5.39; N, 5.76; measured element content (%): C, 88.81; H, 5.50; N, 5.68. The above analysis results indicated that the obtained product was the expected product.
实施例40：化合物40的合成：Embodiment 40: the synthesis of compound 40:
依照化合物31的合成，步骤相同，用4-甲氧基苯胺代替苯胺，3-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物40(1.29g，产率68％)，质谱分析确定的分子离子质量为：946.53(计算值为：946.37)；理论元素含量(％)C69H46N4O：C，87.50；H，4.90；N，5.92；实测元素含量(％)：C，87.66；H，4.81；N，5.83。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, with 4-methoxyaniline instead of aniline, 3-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 40 (1.29g, yield 68%), mass spectrometry determined Molecular ion mass: 946.53 (calculated value: 946.37); theoretical element content (%) C 69 H 46 N 4 O: C, 87.50; H, 4.90; N, 5.92; measured element content (%): C, 87.66 ; H, 4.81; N, 5.83. The above analysis results indicated that the obtained product was the expected product.
实施例41：化合物41的合成：Example 41: Synthesis of Compound 41:
依照化合物31的合成，步骤相同，用4-氰基苯胺代替苯胺，3-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物41(1.24g，产率66％)，质谱分析确定的分子离子质量为：941.49(计算值为：941.35)；理论元素含量(％)C69H43N5：C，87.97；H，4.60；N，7.43；实测元素含量(％)：C，88.05；H，4.62；N，7.33。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, with 4-cyanoaniline instead of aniline, and 3-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 41 (1.24g, yield 66%), the molecule determined by mass spectrometry analysis Ion mass: 941.49 (calculated value: 941.35); theoretical element content (%) C 69 H 43 N 5 : C, 87.97; H, 4.60; N, 7.43; measured element content (%): C, 88.05; H , 4.62; N, 7.33. The above analysis results indicated that the obtained product was the expected product.
实施例42：化合物42的合成：Example 42: Synthesis of Compound 42:
依照化合物31的合成，步骤相同，用4-甲基苯胺代替苯胺，2-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物42(1.21g，产率65％)，质谱分析确定的分子离子质量为：930.52(计算值为：930.37)；理论元素含量(％)C69H46N4：C，89.00；H，4.98；N，6.02；实测元素含量(％)：C，88.85；H，5.08；N，6.07。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, with 4-methylaniline instead of aniline, and 2-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 42 (1.21g, yield 65%), the molecule determined by mass spectrometry Ion mass: 930.52 (calculated value: 930.37); theoretical element content (%) C 69 H 46 N 4 : C, 89.00; H, 4.98; N, 6.02; measured element content (%): C, 88.85; H , 5.08; N, 6.07. The above analysis results indicated that the obtained product was the expected product.
实施例43：化合物43的合成：Example 43: Synthesis of Compound 43:
依照化合物31的合成，步骤相同，用4-叔丁基苯胺代替苯胺，2-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物43(1.34g，产率69％)，质谱分析确定的分子离子质量为：972.61(计算值为：972.42)；理论元素含量(％)C72H52N4：C，88.86；H，5.39；N，5.76；实测元素含量(％)：C，88.91；H，5.26；N，5.82。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, with 4-tert-butylaniline instead of aniline, 2-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 43 (1.34g, yield 69%), mass spectrometry determined Molecular ion mass: 972.61 (calculated value: 972.42); theoretical element content (%) C 72 H 52 N 4 : C, 88.86; H, 5.39; N, 5.76; measured element content (%): C, 88.91; H, 5.26; N, 5.82. The above analysis results indicated that the obtained product was the expected product.
实施例44：化合物44的合成：Example 44: Synthesis of Compound 44:
依照化合物31的合成，步骤相同，用4-甲氧基苯胺代替苯胺，2-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物44(1.19g，产率63％)，质谱分析确定的分子离子质量为：946.49(计算值为：946.37)；理论元素含量(％)C69H46N4O：C，87.50；H，4.90；N，5.92；实测元素含量(％)：C，87.56；H，4.94；N，5.82。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, with 4-methoxyaniline instead of aniline, 2-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 44 (1.19g, yield 63%), mass spectrometry determined Molecular ion mass: 946.49 (calculated value: 946.37); theoretical element content (%) C 69 H 46 N 4 O: C, 87.50; H, 4.90; N, 5.92; measured element content (%): C, 87.56 ; H, 4.94; N, 5.82. The above analysis results indicated that the obtained product was the expected product.
实施例45：化合物45的合成：Example 45: Synthesis of Compound 45:
依照化合物31的合成，步骤相同，用4-氰基苯胺代替苯胺，2-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物45(1.11g，产率59％)，质谱分析确定的分子离子质量为：941.58(计算值为：941.35)；理论元素含量(％)C69H43N5：C，87.97；H，4.60；N，7.43；实测元素含量(％)：C，88.15；H，4.52；N，7.32。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, with 4-cyanoaniline instead of aniline, and 2-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 45 (1.11g, yield 59%), the molecule determined by mass spectrometry analysis Ion mass: 941.58 (calculated value: 941.35); theoretical element content (%) C 69 H 43 N 5 : C, 87.97; H, 4.60; N, 7.43; measured element content (%): C, 88.15; H , 4.52; N, 7.32. The above analysis results indicated that the obtained product was the expected product.
实施例46：化合物46的合成：Example 46: Synthesis of compound 46:
依照化合物31的合成，步骤相同，用3-甲基苯胺代替苯胺，得到白色粉末状化合物46(1.30g，产率70％)，质谱分析确定的分子离子质量为：930.52(计算值为：930.37)；理论元素含量(％)C69H46N4：C，89.00；H，4.98；N，6.02；实测元素含量(％)：C，89.05；H，4.82；N，60.12。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, and 3-methylaniline is used instead of aniline to obtain white powder compound 46 (1.30 g, yield 70%), and the molecular ion mass determined by mass spectrometry is: 930.52 (calculated value: 930.37 ); theoretical element content (%) C 69 H 46 N 4 : C, 89.00; H, 4.98; N, 6.02; measured element content (%): C, 89.05; H, 4.82; N, 60.12. The above analysis results indicated that the obtained product was the expected product.
实施例47：化合物47的合成：Example 47: Synthesis of Compound 47:
依照化合物31的合成，步骤相同，用3-叔丁基苯胺代替苯胺，得到白色粉末状化合物47(1.28g，产率66％)，质谱分析确定的分子离子质量为：972.65(计算值为：972.42)；理论元素含量(％)C72H52N4：C，88.86；H，5.39；N，5.76；实测元素含量(％)：C，88.96；H，5.33；N，5.71。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, and aniline is replaced with 3-tert-butylaniline to obtain white powder compound 47 (1.28g, yield 66%), and the molecular ion mass determined by mass spectrometry is: 972.65 (the calculated value is: 972.42); theoretical element content (%) C 72 H 52 N 4 : C, 88.86; H, 5.39; N, 5.76; measured element content (%): C, 88.96; H, 5.33; N, 5.71. The above analysis results indicated that the obtained product was the expected product.
实施例48：化合物48的合成：Example 48: Synthesis of Compound 48:
依照化合物31的合成，步骤相同，用3-甲氧基苯胺代替苯胺，得到白色粉末状化合物48(1.34g，产率71％)，质谱分析确定的分子离子质量为：946.43(计算值为：946.37)；理论元素含量(％)C69H46N4O：C，87.50；H，4.90；N，5.92；实测元素含量(％)：C，87.56；H，4.93；N，5.80。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, and 3-methoxyaniline is used instead of aniline to obtain white powder compound 48 (1.34g, yield 71%), and the molecular ion mass determined by mass spectrometry is: 946.43 (the calculated value is: 946.37); theoretical element content (%) C 69 H 46 N 4 O: C, 87.50; H, 4.90; N, 5.92; measured element content (%): C, 87.56; H, 4.93; N, 5.80. The above analysis results indicated that the obtained product was the expected product.
实施例49：化合物49的合成：Example 49: Synthesis of Compound 49:
依照化合物31的合成，步骤相同，用3-氰基苯胺代替苯胺，得到白色粉末状化合物49(1.13g，产率60％)，质谱分析确定的分子离子质量为：941.48(计算值为：941.35)；理论元素含量(％)C69H43N5：C，87.97；H，4.60；N，7.43；实测元素含量(％)：C，87.90；H，4.72；N，7.38。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, and 3-cyanoaniline is used instead of aniline to obtain white powder compound 49 (1.13 g, yield 60%), and the molecular ion mass determined by mass spectrometry is: 941.48 (calculated value: 941.35 ); theoretical element content (%) C 69 H 43 N 5 : C, 87.97; H, 4.60; N, 7.43; measured element content (%): C, 87.90; H, 4.72; N, 7.38. The above analysis results indicated that the obtained product was the expected product.
实施例50：化合物50的合成：Embodiment 50: the synthesis of compound 50:
依照化合物31的合成，步骤相同，用3-甲基苯胺代替苯胺，3-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物50(1.28g，产率69％)，质谱分析确定的分子离子质量为：930.60(计算值为：930.37)；理论元素含量(％)C69H46N4：C，89.00；H，4.98；N，6.02；实测元素含量(％)：C，89.13；H，4.92；N，5.95。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, with 3-methylaniline instead of aniline, and 3-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 50 (1.28g, yield 69%), the molecule determined by mass spectrometry analysis Ion mass: 930.60 (calculated value: 930.37); theoretical element content (%) C 69 H 46 N 4 : C, 89.00; H, 4.98; N, 6.02; measured element content (%): C, 89.13; H , 4.92; N, 5.95. The above analysis results indicated that the obtained product was the expected product.
实施例51：化合物51的合成：Example 51: Synthesis of Compound 51:
依照化合物31的合成，步骤相同，用3-叔丁基苯胺代替苯胺，3-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物51(1.34g，产率69％)，质谱分析确定的分子离子质量为：972.59(计算值为：972.42)；理论元素含量(％)C72H52N4：C，88.86；H，5.39；N，5.76；实测元素含量(％)：C，88.69；H，5.48；N，5.82。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, with 3-tert-butylaniline instead of aniline, 3-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 51 (1.34g, yield 69%), mass spectrometry determined Molecular ion mass: 972.59 (calculated value: 972.42); theoretical element content (%) C 72 H 52 N 4 : C, 88.86; H, 5.39; N, 5.76; measured element content (%): C, 88.69; H, 5.48; N, 5.82. The above analysis results indicated that the obtained product was the expected product.
实施例52：化合物52的合成：Example 52: Synthesis of Compound 52:
依照化合物31的合成，步骤相同，用3-甲基苯胺代替苯胺，3-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物52(1.12g，产率59％)，质谱分析确定的分子离子质量为：946.58(计算值为：946.37)；理论元素含量(％)C69H46N4O：C，87.50；H，4.90；N，5.92；实测元素含量(％)：C，87.46；H，4.84；N，6.00。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, with 3-methylaniline instead of aniline, and 3-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 52 (1.12g, yield 59%), the molecule determined by mass spectrometry analysis Ion mass: 946.58 (calculated value: 946.37); theoretical element content (%) C 69 H 46 N 4 O: C, 87.50; H, 4.90; N, 5.92; measured element content (%): C, 87.46; H, 4.84; N, 6.00. The above analysis results indicated that the obtained product was the expected product.
实施例53：化合物53的合成：Example 53: Synthesis of Compound 53:
依照化合物31的合成，步骤相同，用3-氰基苯胺代替苯胺，3-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物53(1.04g，产率55％)，质谱分析确定的分子离子质量为：941.63(计算值为：941.35)；理论元素含量(％)C69H43N5：C，87.97；H，4.60；N，7.43；实测元素含量(％)：C，87.85；H，4.66；N，7.49。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, with 3-cyanoaniline instead of aniline, and 3-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 53 (1.04 g, yield 55%), the molecule determined by mass spectrometry analysis Ion mass: 941.63 (calculated value: 941.35); theoretical element content (%) C 69 H 43 N 5 : C, 87.97; H, 4.60; N, 7.43; measured element content (%): C, 87.85; H , 4.66; N, 7.49. The above analysis results indicated that the obtained product was the expected product.
实施例54：化合物54的合成：Example 54: Synthesis of Compound 54:
依照化合物31的合成，步骤相同，用3-甲基苯胺代替苯胺，2-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物54(1.10g，产率59％)，质谱分析确定的分子离子质量为：930.56(计算值为：930.37)；理论元素含量(％)C69H46N4：C，89.00；H，4.98；N，6.02；实测元素含量(％)：C，89.05；H，5.08；N，5.87。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, with 3-methylaniline instead of aniline, 2-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 54 (1.10g, yield 59%), the molecule determined by mass spectrometry analysis Ion mass: 930.56 (calculated value: 930.37); theoretical element content (%) C 69 H 46 N 4 : C, 89.00; H, 4.98; N, 6.02; measured element content (%): C, 89.05; H , 5.08; N, 5.87. The above analysis results indicated that the obtained product was the expected product.
实施例55：化合物55的合成：Example 55: Synthesis of Compound 55:
依照化合物31的合成，步骤相同，用3-叔丁基苯胺代替苯胺，2-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物55(1.13g，产率58％)，质谱分析确定的分子离子质量为：972.61(计算值为：972.42)；理论元素含量(％)C72H52N4：C，88.86；H，5.39；N，5.76；实测元素含量(％)：C，88.96；H，5.36；N，5.67。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, with 3-tert-butylaniline instead of aniline, 2-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 55 (1.13g, yield 58%), mass spectrometry determined Molecular ion mass: 972.61 (calculated value: 972.42); theoretical element content (%) C 72 H 52 N 4 : C, 88.86; H, 5.39; N, 5.76; measured element content (%): C, 88.96; H, 5.36; N, 5.67. The above analysis results indicated that the obtained product was the expected product.
实施例56：化合物56的合成：Example 56: Synthesis of Compound 56:
依照化合物31的合成，步骤相同，用3-甲基苯胺代替苯胺，2-溴苯甲醛代替对溴苯甲醛，得到白色粉末状化合物56(1.19g，产率63％)，质谱分析确定的分子离子质量为：946.57(计算值为：946.37)；理论元素含量(％)C69H46N4O：C，87.50；H，4.90；N，5.92；实测元素含量(％)：C，87.36；H，4.94；N，6.02。上述分析结果表明，获得的产物为预计的产品。According to the synthesis of compound 31, the steps are the same, with 3-methylaniline instead of aniline, 2-bromobenzaldehyde instead of p-bromobenzaldehyde, to obtain white powder compound 56 (1.19g, yield 63%), the molecule determined by mass spectrometry Ion mass: 946.57 (calculated value: 946.37); theoretical element content (%) C 69 H 46 N 4 O: C, 87.50; H, 4.90; N, 5.92; measured element content (%): C, 87.36; H, 4.94; N, 6.02. The above analysis results indicated that the obtained product was the expected product.
实施例57：发光器件[ITO/NPB/化合物9/TPBI/LiF/Al]Example 57: Light-emitting device [ITO/NPB/Compound 9/TPBI/LiF/Al]
在镀有ITO阳极的玻璃基片上依次蒸镀空穴传输层NPB(厚度为50nm)，发光层为实施例9制备的化合物9(20nm)，电子传输层TPBI(30nm)，电子注入材料LiF(0.5nm)，Al阴极在蒸镀过程中保持压力为5×10-6Pa。该器件开启电压为3.9V，最大电流效率可达1.83cd/A，功率效率1.48lm/W，外量子效率2.30％。该器件发深蓝光，亮度可达3095cd/m2。The hole transport layer NPB (thickness is 50nm) is evaporated successively on the glass substrate that is coated with ITO anode, and light-emitting layer is the compound 9 (20nm) that embodiment 9 prepares, electron transport layer TPBI (30nm), electron injection material LiF ( 0.5nm), Al cathode The pressure was kept at 5×10 -6 Pa during the evaporation process. The turn-on voltage of the device is 3.9V, the maximum current efficiency can reach 1.83cd/A, the power efficiency is 1.48lm/W, and the external quantum efficiency is 2.30%. The device emits deep blue light with a brightness of up to 3095cd/m 2 .
实施例58：发光器件[ITO/NPB/化合物32/TPBI/LiF/Al]Example 58: Light emitting device [ITO/NPB/Compound 32/TPBI/LiF/Al]
在镀有ITO阳极的玻璃基片上依次蒸镀空穴传输层NPB(厚度为50nm)，发光层为实施例32制备的化合物32(20nm)，电子传输层TPBI(30nm)，电子注入材料LiF(0.5nm)，Al阴极在蒸镀过程中保持压力为5×10-6Pa。该器件开启电压为3.3V，最大电流效率可达4.13cd/A，功率效率2.89lm/W，外量子效率3.69％。该器件发深蓝光，亮度可达13740cd/m2。The hole transport layer NPB (thickness is 50nm) is evaporated successively on the glass substrate that is coated with ITO anode, and light-emitting layer is the compound 32 (20nm) that embodiment 32 prepares, electron transport layer TPBI (30nm), electron injection material LiF ( 0.5nm), Al cathode The pressure was kept at 5×10 -6 Pa during the evaporation process. The turn-on voltage of the device is 3.3V, the maximum current efficiency can reach 4.13cd/A, the power efficiency is 2.89lm/W, and the external quantum efficiency is 3.69%. The device emits deep blue light with a brightness of up to 13740cd/m 2 .
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| CN106432353B (en) * | 2016-09-23 | 2018-10-12 | 苏州科技大学 | Enhance ruthenium complex, its preparation method and the application of characteristic with aggregated-state induced phosphorescence |
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