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CN-121991133-A - Organic metal compound and preparation method and application thereof

CN121991133ACN 121991133 ACN121991133 ACN 121991133ACN-121991133-A

Abstract

The invention discloses an organic metal compound, a preparation method and application thereof, and relates to the technical field of organic electroluminescence. According to the invention, by introducing some benzene, biphenyl and other functional groups into the dibenzofuran ring main body and adding some electron withdrawing groups such as cyano groups or methyl groups into the benzene ring, compared with the compound of the comparative example, the compound of the invention has the advantages that the molecular configuration is changed, the conjugated system is increased, the electrochemical characteristics of the compound are regulated, and after the obtained organic compound is used for an organic electroluminescent device, the starting voltage of the device is reduced, and the luminous efficiency and the service life of the device are improved.

Inventors

  • WANG HUI
  • MOU YANG
  • LIU HUAN
  • CHAI LIPENG
  • ZHAO JIAXU
  • GUO YANLIANG
  • YIN JIAN

Assignees

  • 吉林奥来德光电材料股份有限公司

Dates

Publication Date
20260508
Application Date
20241107

Claims (6)

  1. 1. An organometallic compound characterized by the structure of formula I: Wherein each of said R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 is independently selected from any one of-H, -D, -T, -F, -CN, -CH 3 、-CD 3 、-CT 3 、-CF 3 、-CH 2 F、-CHF 2 , silicon-based, germanium-based, substituted or unsubstituted C 2 -C 10 alkyl, substituted or unsubstituted C 3 -C 8 cycloalkyl, substituted or unsubstituted C 6 -C 20 aryl, substituted or unsubstituted 4-to 8-membered heterocyclyl; Each R 13 、R 14 、R 15 、R 16 is independently selected from H and at least one substituent is S 1 ; the N 1 、N 2 、N 3 、N 4 、N 5 、N 6 groups are each independently selected from H, and at least three are simultaneously independently selected from substituted or unsubstituted phenyl groups.
  2. 2. An organometallic compound according to claim 1, characterized in that the ligand L A is selected from any of the following structures L A -1～L A -96:
  3. 3. An organometallic compound according to claim 1, characterized in that the ligand L B is selected from any of the following structures L B -1～L B -90:
  4. 4. an organometallic compound according to claim 1, characterized in that the formula I is selected from any of the following structures L-1 to L-900:
  5. 5. a process for the preparation of an organometallic compound as claimed in any of claims 1 to 4, characterized by the following synthetic route: the substituents in the formulae above are as defined in any of claims 1 to 4; the method comprises the following specific steps: Adding a raw material L-A under the condition of nitrogen, reacting iridium trichloride, ethylene glycol diethyl ether and water at 120 ℃ for 48 hours, performing suction filtration, leaching with ethanol and petroleum ether, and drying to obtain an intermediate L-A1 Adding an intermediate L-A1, silver trifluoromethane sulfonate, isopropanol and dichloromethane under the condition of nitrogen, reacting for 48 hours at 25 ℃, then passing through a silica gel funnel, leaching with the dichloromethane until no product exists, and merging organic phases to spin dry to obtain an intermediate L-A2; and thirdly, adding intermediates L-A2 and L-B under the condition of nitrogen, reacting for 48 hours at 90 ℃ with ethanol, and then performing suction filtration, wherein the product L is obtained by column chromatography.
  6. 6. Use of an organometallic compound according to claims 1-4 or an organometallic compound obtained by a process for preparing an organometallic compound according to claim 5 in an organic electroluminescent device.

Description

Organic metal compound and preparation method and application thereof Technical Field The invention relates to the technical field of organic electroluminescence, in particular to an organic metal compound and a preparation method and application thereof. Background An Organic LIGHT EMITTING (OLED) is a device with a sandwich-like structure, and includes positive and negative electrode layers and an Organic functional material layer sandwiched between the electrode layers. When a voltage is applied to the electrode of the OLED device, positive charges are injected from the positive electrode, negative charges are injected from the negative electrode, and positive charges and negative charges migrate in the organic layer to meet and recombine to emit light under the action of an electric field. Because the OLED device has the advantages of high brightness, quick response, wide viewing angle, simple process, flexibility and the like, the OLED device has a great deal of attention in the novel display technical field and the novel illumination technical field. At present, the OLED device is widely applied to display panels of products such as novel illumination lamps, smart phones and tablet computers, and further expands the application field of large-size display products such as televisions, so that the OLED device is a novel display technology with rapid development and high technical requirements. And research on high-efficiency phosphorescent organic electroluminescent devices provides an important driving force for the development of flat panels and portable display industries. Therefore, how to develop a high performance phosphorescent material that can provide the organic electroluminescent device with high efficiency, long lifetime, low voltage and other comprehensive characteristics is a technical problem that needs to be solved by those skilled in the art. Disclosure of Invention In view of the above, the present invention provides an organometallic compound which, after being used in an organic electroluminescent device, reduces the starting voltage of the device, and improves the luminous efficiency and lifetime of the device, and a method for preparing the same and applications thereof. In order to achieve the above purpose, the present invention adopts the following technical scheme: An organometallic compound having the structure shown in formula I: Wherein each of said R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12 is independently selected from any one of-H, -D, -T, -F, -CN, -CH 3、-CD3、-CT3、-CF3、-CH2F、-CHF2, silicon-based, germanium-based, substituted or unsubstituted C 2-C10 alkyl, substituted or unsubstituted C 3-C8 cycloalkyl, substituted or unsubstituted C 6-C20 aryl, substituted or unsubstituted 4-to 8-membered heterocyclyl; Each R 13、R14、R15、R16 is independently selected from H and at least one substituent is S 1; the N 1、N2、N3、N4、N5、N6 groups are each independently selected from H, and at least three are simultaneously independently selected from substituted or unsubstituted phenyl groups. Preferably, ligand L A is selected from any one of the following structures L A-1～LA -96: Preferably, ligand L B is selected from any one of the following structures L B-1～LB -90: preferably, the formula I is selected from any one of the following structures L-1 to L-900: Another object of the present invention is to provide a method for preparing the above organometallic compound, the synthetic route is as follows: the substituents in the formulae described above are the same as the substituents in the organometallic compounds described above; the method comprises the following specific steps: Adding a raw material L-A under the condition of nitrogen, reacting iridium trichloride, ethylene glycol diethyl ether and water at 120 ℃ for 48 hours, performing suction filtration, leaching with ethanol and petroleum ether, and drying to obtain an intermediate L-A1 Adding an intermediate L-A1, silver trifluoromethane sulfonate, isopropanol and dichloromethane under the condition of nitrogen, reacting for 48 hours at 25 ℃, then passing through a silica gel funnel, leaching with the dichloromethane until no product exists, and merging organic phases to spin dry to obtain an intermediate L-A2; and thirdly, adding intermediates L-A2 and L-B under the condition of nitrogen, reacting for 48 hours at 90 ℃ with ethanol, and then performing suction filtration, wherein the product L is obtained by column chromatography. It is also an object of the present invention to provide the use of the organometallic compounds described above in organic electroluminescent devices. Compared with the prior art, the invention has the following beneficial effects: The organic electroluminescent device provided by the invention adopts a doping material with a specific structure, and by introducing some benzene, biphenyl and other functional groups into the dibenzofuran ring main body and adding some electron withdrawing groups such as cyano g