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CN-122010989-A - Organic compound and application thereof

CN122010989ACN 122010989 ACN122010989 ACN 122010989ACN-122010989-A

Abstract

The invention provides an organic compound and application thereof, wherein the organic compound has a structure shown in a formula I, and the organic compound has narrow emission spectrum characteristics and high luminous efficiency of a multi-resonance material and realizes the purpose of regulating light color through the design of a molecular structure and mutual compounding of groups. The organic compound has excellent electroluminescent performance, narrow spectral characteristics and thermal stability, is used for an organic electroluminescent device, can be used as a fluorescent doping material of a luminescent layer, can effectively improve service life attenuation and efficiency roll-off of the device, improves the luminescent efficiency of the device, prolongs the service life of the device, reduces voltage, ensures that the device has higher color purity, and endows the device with more excellent comprehensive luminescent effect.

Inventors

  • LI YILANG
  • GENG QINGKAI
  • JIA XIAOQIN
  • LI GUOMENG

Assignees

  • 北京鼎材科技股份有限公司

Dates

Publication Date
20260512
Application Date
20241031

Claims (14)

  1. 1. An organic compound, characterized in that the organic compound has a structure as shown in formula I: Wherein each M 1 、M 2 is independently selected from any one of O, S or NR 1 ; R 1 is selected from any one of R P , substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, wherein R 1 is not connected with an adjacent ring structure or is connected with a chemical bond to form a ring; Ring A, ring B, ring C are each independently selected from any one of an unsubstituted or R A -substituted C6-C60 aromatic ring, an unsubstituted or R A -substituted C3-C60 heteroaromatic ring; R A is independently selected from any one of R P , halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, wherein R A is independently not connected with an adjacent ring structure or is connected through a chemical bond to form a ring; At least one of the rings A, B, C, R 1 has a structure as shown in formula a, and at least one of R 1 is a group R P , and/or at least one of R A is a group R P , and R P has a structure as shown in formula B; ,Z 1 、Z 2 、Z 3 、Z 4 、Z 5 、Z 6 、Z 7 、Z 8 、Z 9 、Z 10 、Z 11 in formula a are each independently selected from any one of C, CR 0 or N; r 0 is independently selected from any one of hydrogen, R P , halogen, substituted or unsubstituted C1-C20 straight or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, cyano, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, each R 0 is independently unconnected to an adjacent ring structure or connected through a chemical bond to form a ring; in the formula b, the amino acid sequence of the formula, represents the linking site of the group; L is selected from any one of substituted or unsubstituted C1-C20 linear or branched alkylene, substituted or unsubstituted C1-C20 linear or branched silylene, substituted or unsubstituted C3-C20 cycloalkylene, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene, substituted or unsubstituted C6-C60 arylsilylene, substituted or unsubstituted C6-C60 arylimino, and substituted or unsubstituted C3-C60 heteroarylimino; ar is selected from any one of unsubstituted or R 2 substituted C14-C60 condensed aryl and unsubstituted or R 2 substituted C13-C60 heteroaryl, and a heteroatom in the C13-C60 heteroaryl is at least one of O, S; R 2 is each independently selected from any one of halogen, substituted or unsubstituted C1-C20 straight or branched chain alkylene, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, cyano, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; The substituent groups of the substituents R 1 、R 2 、R A 、R 0 and L are each independently selected from any one or a combination of at least two of halogen, cyano, amino, C1-C20 straight-chain or branched-chain alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl and C3-C60 heteroaryl, and the substituent groups are each independently not connected with adjacent ring structures or are connected through chemical bonds to form a ring.
  2. 2. The organic compound according to claim 1, wherein the organic compound has a structure as shown in formula II: Wherein M 1 、M 2 , ring A, ring B have the same defined ranges as formula I; each X 1 、X 2 、X 3 is independently selected from CR 11 or N; R 11 is independently selected from any one of hydrogen, R P , halogen, cyano, substituted or unsubstituted C1-C20 straight or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and R 11 is independently not connected with an adjacent ring structure or is connected with a chemical bond to form a ring.
  3. 3. The organic compound according to claim 1, wherein the organic compound has a structure as shown in any one of formulas III-1 to III-15: Wherein M 1 、M 2 , ring a, ring B have the same defined range ;Z 1 、Z 2 、Z 3 、Z 4 、Z 5 、Z 6 、Z 7 、Z 8 、Z 9 、Z 10 、Z 11 as in formula I and have the same defined range as in formula a; each X 1 、X 2 、X 3 is independently selected from CR 11 or N; R 11 is each independently selected from any one of hydrogen, R P , halogen, cyano, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, each R 11 is independently unconnected to an adjacent ring structure or connected by a chemical bond to form a ring; The dotted line represents a single bond or no connection.
  4. 4. The organic compound according to claim 3, wherein the organic compound has a structure as shown in any one of formulas IV-1 to IV-14: Wherein M 1 、M 2 has the same definition as in formula I ;Z 1 、Z 2 、Z 3 、Z 4 、Z 5 、Z 6 、Z 7 、Z 8 、Z 9 、Z 10 、Z 11 and has the same definition as in formula a; each X 1 、X 2 、X 3 is independently selected from CR 11 or N; Each X 4 、X 5 、X 6 、X 7 、X 8 、X 9 、X 10 is independently selected from CR B or N; M 3 is any one selected from O, S, se, NR m1 、CR m2 R m3 or SiR m4 R m5 ; r 11 、R B is each independently selected from any one of hydrogen, R P , halogen, cyano, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, each R 11 、R B is independently unconnected to an adjacent ring structure or connected by a chemical bond to form a ring; R m1 、R m2 、R m3 、R m4 、R m5 is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 linear or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, wherein R m2 and R m3 are not connected or are connected through a chemical bond to form a ring, and R m4 and R m5 are not connected or are connected through a chemical bond to form a ring.
  5. 5. The organic compound according to claim 4, wherein at least one of formula IV-1, formula IV-2 and formula IV-3, formula IV-9, formula IV-10, formula IV-11, formula IV-12, formula IV-13 and formula IV-14 is NR 1 ; Preferably, in formula IV-1, formula IV-2, formula IV-3, formula IV-9, formula IV-10, formula IV-11, formula IV-12, formula IV-13 and formula IV-14, M 2 is NR 1 , and M 1 is selected from any one of O, S or NR 1 ; preferably, the R 1 is selected from any one of R P , substituted or unsubstituted C6-C20 aryl and substituted or unsubstituted C3-C20 heteroaryl, and further preferably any one of R P , substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl and 9-phenylcarbazolyl.
  6. 6. The organic compound according to claim 4, wherein each X 1 、X 2 、X 3 is independently selected from CR 11 ; preferably, each R 11 is independently selected from any one of hydrogen, R P , substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, further preferably any one of hydrogen, R P , C1-C6 straight or branched alkyl, substituted or unsubstituted C6-C12 aryl; Preferably, each of said xs 4 、X 5 、X 6 、X 7 、X 8 、X 9 、X 10 is independently selected from CR B ; Preferably, each R B is independently selected from any one of hydrogen, R P , substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, substituted or unsubstituted C6-C20 aryloxy, substituted or unsubstituted C3-C20 heteroaryloxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C30 heteroarylamino; Preferably, each of said Z 1 、Z 2 、Z 3 、Z 4 、Z 5 、Z 6 、Z 7 、Z 8 、Z 9 、Z 10 、Z 11 is independently selected from CR 0 ; Preferably, each R 0 is independently selected from any one of hydrogen, R P , halogen, cyano, substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, substituted or unsubstituted C6-C20 aryloxy.
  7. 7. The organic compound according to claim 1, wherein the organic compound has a structure as shown in any one of formulas V-1 to V-14: wherein the dotted line represents a single bond or no linkage; m 1 is selected from any one of O, S or NR 1 ; M 3 is selected from any one of O, S, NR m1 or CR m2 R m3 ; R m1 、R m2 、R m3 is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 linear or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, wherein R m2 and R m3 are not connected or are connected through a chemical bond to form a ring; R 1 is selected from any one of R P , substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, wherein R 1 is not connected with an adjacent ring structure or is connected with a chemical bond to form a ring; R 11 、R B1 、R B2 、R 21 、R 31 、R 32 each independently represents unsubstituted, monosubstituted to maximally permissible substitution; R 11 、R B1 、R B2 、R 31 、R 32 is independently selected from any one of hydrogen, R P , halogen, cyano, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, each R 11 、R B1 、R B2 is independently unconnected to an adjacent ring structure or connected by a chemical bond to form a ring, and any adjacent at least two groups in R 11 、R B1 、R B2 are unconnected or connected by a chemical bond to form a ring; At least one of the R 1 、R 11 、R B1 、R B2 、R 31 、R 32 groups is a group R P ; R 21 is each independently selected from any one or a combination of at least two of hydrogen, halogen, cyano, amino, C1-C20 straight or branched chain alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl.
  8. 8. The organic compound according to claim 7, wherein R 1 is selected from any one of R P , substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, preferably any one of R P , substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, 9-phenylcarbazolyl; preferably, each R 11 is independently selected from any one of hydrogen, R P , substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, further preferably any one of hydrogen, R P , C1-C6 straight or branched alkyl, substituted or unsubstituted C6-C12 aryl; Preferably, each R B1 、R B2 is independently selected from any one of hydrogen, R P , substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, substituted or unsubstituted C6-C20 aryloxy, substituted or unsubstituted C3-C20 heteroaryloxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C30 heteroarylamino, further preferably any one of hydrogen, R P , substituted or unsubstituted C1-C10 straight or branched alkyl, phenyl, naphthyl, biphenyl, terphenyl, diphenylamino, phenoxy, pyridyl, pyridyloxy, pyridylphenylamino; Preferably, the substituents in R B1 、R B2 are each independently selected from any one or a combination of at least two of halogen, cyano, C1-C10 straight or branched chain alkyl, C2-C10 alkenyl, C3-C10 cycloalkyl, C6-C20 aryl, C3-C20 heteroaryl, C6-C30 arylamino, each of the substituents in R B1 、R B2 is independently unconnected to an adjacent ring structure or connected by a chemical bond; Preferably, each R 21 is independently selected from any one of hydrogen, C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, C6-C20 aryl.
  9. 9. An organic compound according to any one of claims 1 to 8, wherein Ar is selected from any one of unsubstituted or R 2 substituted C14-C40 fused aryl, unsubstituted or R 2 substituted C13-C40 heteroaryl, preferably any one of unsubstituted or R 2 substituted: wherein — represents the attachment site of the group; Preferably, each R 2 is independently selected from any one of halogen, cyano, substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, substituted or unsubstituted C6-C20 aryloxy, substituted or unsubstituted C3-C20 heteroaryloxy, substituted or unsubstituted C6-C30 arylamino, further preferably any one of halogen, cyano, unsubstituted or halogenated C1-C6 straight or branched alkyl, C1-C6 alkoxy, cyclohexyl, substituted or unsubstituted phenyl, naphthyl, biphenyl, diphenylamino, pyridyl, phenoxy, pyridyloxy, dibenzofuranyl, dibenzothienyl.
  10. 10. The organic compound according to any one of claims 1 to 8, wherein L is selected from any one of a substituted or unsubstituted C1-C10 linear or branched alkylene group, a substituted or unsubstituted C1-C10 linear or branched silylene group, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C3-C20 heteroarylene group, a substituted or unsubstituted C6-C20 arylalkylene group, a substituted or unsubstituted C3-C20 heteroarylimino group; Preferably, the L is selected from any one of substituted or unsubstituted C1-C6 linear or branched alkylene, substituted or unsubstituted: wherein — represents the attachment site of the group; Y is selected from O, S, NR 41 、CR 42 R 43 or SiR 44 R 45 ; R 41 、R 42 、R 43 、R 44 、R 45 is independently selected from any one or a combination of at least two of C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C6-C30 aryl and C3-C30 heteroaryl, wherein R 42 and R 43 are not connected or are connected through a chemical bond to form a ring, and R 44 and R 45 are not connected or are connected through a chemical bond to form a ring; r 46 、R 47 is independently selected from any one of C1-C10 straight-chain or branched-chain alkyl and C6-C20 aryl; R 48 is selected from any one of C6-C20 aryl or C3-C20 heteroaryl; Preferably, each R 41 、R 42 、R 43 、R 44 、R 45 is independently selected from any one or a combination of at least two of C1-C10 straight or branched chain alkyl, C2-C10 alkenyl, C6-C20 aryl; preferably, the substituents of the substituents in L are each independently selected from any one of halogen, cyano, C1-C10 straight or branched alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C6-C20 aryl, C3-C20 heteroaryl.
  11. 11. The organic compound according to claim 1, wherein the organic compound has a structure as shown in any one of M001-M216:
  12. 12. Use of an organic compound according to any one of claims 1 to 11, wherein the organic compound is applied to an organic electronic device; preferably, the organic electronic device comprises an organic electroluminescent device; preferably, the organic compound is used as a light emitting layer material in an organic electroluminescent device.
  13. 13. An organic electroluminescent device, comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises at least one organic compound according to any one of claims 1-11; preferably, the organic layer comprises a light-emitting layer comprising at least one organic compound according to any one of claims 1 to 11; preferably, the light emitting layer comprises a host material and a doping material comprising at least one organic compound according to any one of claims 1-11.
  14. 14. A display device characterized in that the display device comprises the organic electroluminescent device according to claim 13.

Description

Organic compound and application thereof Technical Field The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to an organic compound and application thereof. Background In recent years, electroluminescent devices (e.g., organic light emitting diodes, OLEDs) based on organic materials have become increasingly popular, and the inherent flexibility of organic materials compared to electroluminescent devices based on inorganic materials has made them very suitable for the manufacture of flexible, thin electroluminescent devices, which can be used to design and produce aesthetically pleasing and cool screens, displays, lighting devices, etc. as desired, with incomparable advantages of inorganic materials. Currently, OLED-based screens and displays have good efficiency and lifetime, but OLED devices having long lifetime, high efficiency and high color purity at the same time remain a difficulty in research and development. With the rapid development of information technology, display technology faces higher requirements, for example, meeting the color gamut standard BT-2020 of image signals in 4K and 8K ages, and the CIEy of green light is 0.797, so that the color gamut coverage rate is remarkably increased. At present, a luminescent material adopting a narrow half-peak width emission spectrum is one of important means for realizing high light color purity, and especially in the current commercialized OLED materials, a green luminescent material mainly adopts a phosphorescent material with wider half-peak width and stronger shoulder at a long wavelength, so that the requirements of high efficiency and excellent color purity are difficult to meet at the same time. In recent years, scientists develop a Thermally Activated Delayed Fluorescence (TADF) material which has both a theoretical exciton utilization ratio of 100% and a narrow emission spectrum, and the material is expected to realize the requirement of high color purity of BT-2020 as an OLED luminescent material, and can ensure higher efficiency. However, the materials have serious efficiency roll-off under high brightness, and the service life of the devices is short, so that the materials can not reach the standards of mass production and use. In order to solve the problem, scientists put forward a super-fluorescence strategy, namely, energy transfer is carried out to transfer excitation state energy of a TADF material or a phosphorescent material to a narrow-spectrum fluorescent material to emit light, so that not only is the exciton utilization rate of 100% theoretically realized, but also a narrow emission spectrum is obtained, and an OLED device with good efficiency, long service life and high color purity is expected to be obtained. However, it is still difficult for the existing fluorescent materials to meet the performance requirements of narrow spectrum, high efficiency and long service life at the same time. In addition, phosphorescent materials are typically based on transition metals, such as iridium, platinum, etc., which are often very expensive in many OLED materials due to their low abundance. Therefore, reducing the amount of phosphorescent material is critical to reduce the cost of the OLED. Accordingly, there is a need in the art to develop a wider variety of organic narrow spectrum luminescent materials with better electroluminescent properties to achieve the above-mentioned desire. Disclosure of Invention Aiming at the defects of the prior art, the invention aims to provide an organic compound and application thereof, which are based on the special design of a molecular structure, so that the organic compound has excellent electroluminescent performance, narrow spectral characteristics and high quantum efficiency, is used for an organic electroluminescent device, can effectively improve the luminous efficiency and service life of the device, reduce voltage and improve color purity. To achieve the purpose, the invention adopts the following technical scheme: In a first aspect, the present invention provides an organic compound having a structure according to formula I: In formula I, M 1、M2 are each independently selected from any one of O, S or NR 1. R 1 is selected from any one of R P, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, wherein R 1 is not connected with an adjacent ring structure or is connected with a chemical bond to form a ring. In the present invention, "R 1 is not connected to the adjacent ring structure" means that R 1 is connected to the N atom only by a single bond, and "R 1 is connected to the adjacent ring structure by a chemical bond to form a ring" means that R 1 is connected to the adjacent ring (e.g., ring A, ring B) by a chemical bond in addition to the N atom to form a condensed ring structure. The following descriptions refer to the same meanings, and are not repeated. Ring A, ring B, ring C are each indep