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CN-121974943-A - Silicon-containing compound and organic electroluminescent device thereof

CN121974943ACN 121974943 ACN121974943 ACN 121974943ACN-121974943-A

Abstract

The invention relates to a silicon-containing compound and an organic electroluminescent device thereof, belonging to the technical field of organic electroluminescent materials. The invention mainly solves the problem that the transmission speeds of the holes and the electrons are not matched, so that the recombination probability of the holes and the electrons in the light-emitting layer is greatly reduced, and the performance of the organic electroluminescent device is reduced. The invention provides a silicon-containing compound which has deeper HOMO energy level, higher oxidation potential and wider band gap, can effectively block holes in a light-emitting layer, and improves the transmission efficiency of electrons, thereby increasing the recombination probability of electrons and holes in the light-emitting layer, improving the light-emitting efficiency of the device and prolonging the service life of the device.

Inventors

  • DU MINGZHU
  • GUO YAO
  • LIANG ZHICONG

Assignees

  • 长春海谱润斯科技股份有限公司

Dates

Publication Date
20260505
Application Date
20260127

Claims (9)

  1. 1. A silicon-containing compound characterized by being represented by formula 1: ; Wherein, the X is O or S; Y is C (R 1 ) or N; Each R 1 、R 1 ' is independently any one or more substituted C6-C30 aryl selected from the group consisting of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C30 heteroaryl, unsubstituted or substituted by deuterium, cyano, fluorine, C1-12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C2-C30 heteroaryl; The R 0 is selected from any one of substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C15 heteroaryl; "substituted" for R 0 refers to independently mono-or poly-substituted with deuterium, tritium, cyano, nitro, hydroxy, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, unsubstituted or substituted with any one or more of the group consisting of deuterium, cyano, fluorine, C1-12 alkyl, silyl, C3-C12 cycloalkyl, C6-C30 aryl; The L 0 、L 1 and L 2 are independently selected from a single bond, any one of the following groups or a combination thereof: ; of the above-mentioned groups, the group, The E is independently C (R 5 ) or N, Z is independently C (R 8 ) or N, and at least two of Z are C and M is independently C (R 9 ) or N, and at least two of M are C and Is connected, L is independently C (R 10 ) or N, R is independently C (R 11 ) or N, and at least one of R is C and Are connected; The T is O or S; The Q is O, S, N (R 13 ) or C (R 14 R 15 ); the U is O or S; the R 2 is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted quinolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl and substituted or unsubstituted isoquinolyl, or two adjacent R 2 are connected to form a substituted or unsubstituted ring; The R 3 is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted isoquinolinyl; the R 4 is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl; Each R 5 、R 8 、R 9 、R 10 、R 11 is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, or two adjacent R 9 are connected to form a substituted or unsubstituted ring, or two adjacent R 10 are connected to form a substituted or unsubstituted ring, or two adjacent R 11 are connected to form a substituted or unsubstituted ring; The R 13 is selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl; R 14 、R 15 is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, or R 14 、R 15 is connected to form a substituted or unsubstituted ring; Said n is selected from 1,2, 3, 4 or 5; The a 1 is selected from 1,2, 3 or 4, a 2 is selected from 1,2 or 3, and a 3 is selected from 1 or 2; The "substituted" group is selected from any one of deuterium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; The compounds are not: 。
  2. 2. The silicon-containing compound according to claim 1, wherein the " "Any one selected from the following groups: ; Each R 1 、R 1 ' is independently any one or more substituted C6-C30 aryl selected from the group consisting of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C30 heteroaryl, unsubstituted or substituted by deuterium, cyano, fluorine, C1-12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C2-C30 heteroaryl; The b 1 is selected from 1, 2, or 3, b 2 is selected from 1 or 2, and b 3 is selected from 1, 2, 3, or 4.
  3. 3. The silicon-containing compound of claim 1, wherein each of L 0 、L 1 and L 2 is independently selected from a single bond, any one of the following groups, or a combination thereof: ; Each R 2 、R 2 ' is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted isoquinolinyl, or a connection between two adjacent R 2 forms a substituted or unsubstituted ring; Each R 3 is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted isoquinolinyl; The R 4 is selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl; Each R 5 、R 8 、R 9 、R 10 、R 11 is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, or two adjacent R 9 are connected to form a substituted or unsubstituted ring, or two adjacent R 10 are connected to form a substituted or unsubstituted ring, or two adjacent R 11 are connected to form a substituted or unsubstituted ring; The R 13 is selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl; R 14 、R 15 is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, or R 14 、R 15 is connected to form a substituted or unsubstituted ring; The a 1 is selected from 1,2, 3 or 4, a 2 is selected from 1,2 or 3, a 3 is selected from 1 or 2, a 4 is selected from 1,2, 3,4, 5 or 6, a 5 is selected from 1,2, 3,4, 5, 6, 7 or 8, a 6 is selected from 1,2, 3,4, 5, 6, 7, 8, 9 or 10.
  4. 4. The silicon-containing compound according to claim 1, wherein R 0 is selected from any one of the following groups: ; The Ra is independently selected from any one or more than one substituted aryl of C6-C30 selected from the group consisting of hydrogen, deuterium, tritium, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, unsubstituted or substituted by deuterium, cyano, fluorine, C1-12 alkyl, silyl, C3-C12 cycloalkyl and C6-C30 aryl, or adjacent Ra are connected with each other to form a substituted or unsubstituted ring; The Rb is independently selected from any one or more substituted C6-C30 aryl groups selected from the group consisting of hydrogen, deuterium, tritium, cyano, nitro, hydroxy, substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted silyl groups, unsubstituted or substituted by deuterium, cyano, fluorine, C1-12 alkyl groups, silyl groups, C3-C12 cycloalkyl groups, and C6-C30 aryl groups, or adjacent Rb are connected with each other to form a substituted or unsubstituted ring; The c 1 is selected from 1,2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, c 2 is selected from 1,2, 3, 4 or 5, c 3 is selected from 1,2, 3 or 4, c 4 is selected from 1 or 2, c 5 is selected from 1,2 or 3, and c 6 is selected from 1,2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15.
  5. 5. The silicon-containing compound according to claim 1, wherein the " "Any one selected from the following groups: ; The Ra is independently selected from any one or more than one substituted aryl of C6-C30 selected from the group consisting of hydrogen, deuterium, tritium, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, unsubstituted or substituted by deuterium, cyano, fluorine, C1-12 alkyl, silyl, C3-C12 cycloalkyl and C6-C30 aryl, or adjacent Ra are connected with each other to form a substituted or unsubstituted ring; The Rb is independently selected from any one or more substituted C6-C30 aryl groups selected from the group consisting of hydrogen, deuterium, tritium, cyano, nitro, hydroxy, substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted silyl groups, unsubstituted or substituted by deuterium, cyano, fluorine, C1-12 alkyl groups, silyl groups, C3-C12 cycloalkyl groups, and C6-C30 aryl groups, or adjacent Rb are connected with each other to form a substituted or unsubstituted ring; The c 1 is selected from 1,2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, c 2 is selected from 1,2, 3, 4 or 5, c 3 is selected from 1,2, 3 or 4, c 4 is selected from 1 or 2, c 5 is selected from 1,2 or 3, and c 6 is selected from 1,2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15.
  6. 6. The silicon-containing compound according to claim 1, wherein the compound represented by formula 1 is selected from any one of the following structures: 。
  7. 7. An organic electroluminescent device comprising an anode, a cathode, and an organic functional layer located between the anode and the cathode or outside any one of the anode and the cathode, characterized in that the organic functional layer comprises any one or more of the silicon-containing compounds according to any one of claims 1 to 6.
  8. 8. The organic electroluminescent device according to claim 7, wherein the organic functional layer comprises a hole transport region, a light emitting layer, and an electron transport region, the hole transport region is located between the anode and the light emitting layer, the light emitting layer is located between the hole transport region and the electron transport region, and the electron transport region is located between the cathode and the light emitting layer, wherein the electron transport region comprises any one or more of the silicon-containing compounds according to any one of claims 1 to 6.
  9. 9. The organic electroluminescent device according to claim 7, wherein the organic functional layer comprises a light efficiency improvement layer located outside any one of the anode and the cathode, wherein the light efficiency improvement layer comprises any one or more of the silicon-containing compounds according to any one of claims 1 to 6.

Description

Silicon-containing compound and organic electroluminescent device thereof Technical Field The invention relates to the field of organic electroluminescent materials, in particular to a silicon-containing compound and an organic electroluminescent device containing the same. Background Research into organic electroluminescent devices (OLEDs) has been rapidly progressed in a few decades. Such devices are favored because of their light weight, thinness, flexibility, ease of manufacture, and low manufacturing cost. In addition, the good performance characteristics of the color enhancement device are that the color enhancement device is not less in color enhancement, such as color emission of a large color gamut, low power consumption, wide viewing angle and the like. This is also one of the main reasons that apple and samsung, etc. companies apply to display applications. However, its application is not limited to displays only. These devices also exhibit good luminous properties, emitting light of uniform color. These properties may be used in other applications such as sensors, OLED bulbs, visible Light Communication (VLC), and other portable applications. Organic electroluminescence is a low-voltage, high-current injection type light emission, and is commonly referred to as an Organic Light Emitting Diode (OLED) because of its properties of a light emitting diode. In an OLED, when a voltage is applied between two electrodes, holes are injected from the anode into the organic material layer and electrons are injected from the cathode into the organic material layer. The injected holes and electrons meet to form excitons, and when these excitons drop to the ground state, light is emitted. However, due to different structural characteristics of the materials, the hole mobility of the hole transport material is two orders of magnitude higher than the electron mobility of the electron transport material, so that the recombination probability of holes and electrons in the light-emitting layer is greatly reduced, and the performance of the device is seriously affected. Therefore, the complete recombination of holes and electrons in the light emitting layer is one of the problems that needs to be solved by current OLED materials. Disclosure of Invention In order to solve the problems in the prior art, the invention provides a silicon-containing compound and an organic electroluminescent device thereof, which can effectively block holes and improve the electron transmission efficiency, thereby improving the performance of the organic electroluminescent device. The invention provides a silicon-containing compound, which is shown as a formula 1: ; Wherein, the X is O or S; Y is C (R 1) or N; Each R 1、R1' is independently any one or more substituted C6-C30 aryl selected from the group consisting of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C30 heteroaryl, unsubstituted or substituted by deuterium, cyano, fluorine, C1-12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C2-C30 heteroaryl; The R 0 is selected from any one of substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C15 heteroaryl; "substituted" for R 0 refers to independently mono-or poly-substituted with deuterium, tritium, cyano, nitro, hydroxy, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, unsubstituted or substituted with any one or more of the group consisting of deuterium, cyano, fluorine, C1-12 alkyl, silyl, C3-C12 cycloalkyl, C6-C30 aryl; The L 0、L1 and L 2 are independently selected from a single bond, any one of the following groups or a combination thereof: ; of the above-mentioned groups, the group, The E is independently C (R 5) or N, Z is independently C (R 8) or N, and at least two of Z are C andM is independently C (R 9) or N, and at least two of M are C andIs connected, L is independently C (R 10) or N, R is independently C (R 11) or N, and at least one of R is C andAre connected; The T is O or S; The Q is O, S, N (R 13) or C (R 14R15); the U is O or S; the R 2 is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted quinolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl and substituted or unsubstituted isoquinolyl, or two adjacent R 2 are connected to form a substituted or unsubstituted ring; The R 3 is independently selected from any one