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CN-121991102-A - Organic compound and application thereof

CN121991102ACN 121991102 ACN121991102 ACN 121991102ACN-121991102-A

Abstract

The invention relates to an organic compound and application thereof, in particular to a polycyclic aromatic compound and application thereof. The aromatic compound of the present invention has a structure represented by the following formula. The aromatic compound is used for an organic electroluminescent device, can effectively improve the efficiency and prolong the service life, and is a blue light material with good performance.

Inventors

  • DENG YAWEN
  • LI YILANG
  • LI GUOMENG

Assignees

  • 北京鼎材科技股份有限公司

Dates

Publication Date
20260508
Application Date
20241030

Claims (11)

  1. 1. A polycyclic aromatic compound having a structure represented by formula (1): in the formula (1), the ring A and the ring B are respectively and independently one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; Y is one of O, S, NAr 1 ; ar 1 is one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, ar 1 is connected or disconnected with ring A, ar 1 is connected or disconnected with ring B; M represents one of a single bond and O, S; R 1 、R 2 is independently selected from one of substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silylalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 arylamino, and substituted or unsubstituted C3-C30 heteroarylamino; U 1 、U 2 、U 3 、U 4 are each independently CR 01 or N; R 01 is independently selected from one of hydrogen, halogen, cyano, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, and two adjacent R 01 are connected in a ring or not; The substitution of each of the above-mentioned substituted or unsubstituted groups in ring A, ring B, ar 1 、R 1 、R 2 、R 01 means that each is independently substituted with a group selected from one or two of deuterium, halogen, cyano, nitro, hydroxy, amino, aldehyde, ester, C1-C20 chain alkyl, C2-C20 alkenyl, C1-C20 alkoxy, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C20 silylalkyl, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl or C3-C30 heteroaryl, each of which is independently unconnected to an adjacent ring structure, or each of which is independently connected to an adjacent ring structure by a chemical bond to form a ring.
  2. 2. The polycyclic aromatic compound according to claim 1, wherein in formula (1), the ring a has a structure as shown in formula (a) or formula (b): in the formulae (a) and (b), the dotted line represents the linking site in the formula (1); X is selected from O or S; U 5 、U 6 、U 7 、U 8 are each independently selected from CR 02 or N; R 02 is independently selected from any one of hydrogen, halogen, cyano, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and adjacent two R 02 are not connected or linked to form a ring; The substitution of each of the substituted or unsubstituted groups described in R 02 means that each is independently substituted with one or a combination of two groups selected from deuterium, halogen, cyano, nitro, hydroxy, amino, aldehyde, ester, C1-C20 chain alkyl, C2-C20 alkenyl, C1-C20 alkoxy, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C20 silylalkyl, C6-C30 aryloxy, C6-C30 arylamino, C6-C30 aryl, or C3-C30 heteroaryl; Preferably, each R 02 is independently selected from any one of hydrogen, halogen, cyano, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, the substituted substituent being any one of halogen, C1-C5 chain alkyl, C6-C18 aryl, C3-C18 heteroaryl.
  3. 3. The polycyclic aromatic compound according to claim 1 or 2, characterized in that in formula (1), the ring B has a structure as shown in formula (c): wherein the dotted line represents the attachment site in formula (1); Each Z 1 、Z 2 、Z 3 is independently selected from CR 03 or N; R 03 is independently selected from any one of hydrogen, halogen, cyano, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 silaaryl, and adjacent two R 03 are not connected or linked to form a ring; The substitution of each of the substituted or unsubstituted groups described in R 03 means that each is independently substituted with one or a combination of two groups selected from deuterium, halogen, cyano, nitro, hydroxy, amino, aldehyde, ester, C1-C20 chain alkyl, C2-C20 alkenyl, C1-C20 alkoxy, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C20 silylalkyl, C6-C30 aryloxy, C6-C30 arylamino, C6-C30 aryl, or C3-C30 heteroaryl; Preferably, each R 03 is independently selected from any one of hydrogen, halogen, cyano, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, and the substituted substituent is any one of halogen, C1-C5 chain alkyl, C6-C18 aryl, and C3-C18 heteroaryl.
  4. 4. The polycyclic aromatic compound according to claim 3, which has a structure represented by the following formula (1-1), formula (1-2), formula (1-3) or formula (1-4): In the formula (1-1), the formula (1-2), the formula (1-3) and the formula (1-4), the definition range of M, R 1 、R 2 、U 1 -U 4 is the same as that in the formula (1), preferably, U 4 is selected from CH or N; X, U 5 -U 8 is the same as the definition in the formula (a) and the formula (b), and Z 1 -Z 3 is the same as the definition in the formula (c); in the formula (1-3), the dotted line represents a connection or disconnection, and M' represents a single bond, O or S; In the formula (1-3) and the formula (1-4), U 9 、U 10 、U 11 、U 12 、U 13 is independently selected from CR 04 or N; R 04 is independently selected from any one of hydrogen, halogen, cyano, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silylalkyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and adjacent two R 04 are not connected or linked to form a ring; The substitution of each of the substituted or unsubstituted groups described in R 04 means that each is independently substituted with one or a combination of two selected from deuterium, halogen, cyano, nitro, hydroxy, amino, aldehyde, ester, C1-C20 chain alkyl, C2-C20 alkenyl, C1-C20 alkoxy, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C20 silylalkyl, C6-C30 aryloxy, C6-C30 arylamino, C6-C30 aryl, or C3-C30 heteroaryl.
  5. 5. The aromatic compound of claim 4 wherein each R 04 is independently selected from any one of hydrogen, halogen, cyano, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silylalkyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and wherein the substituted substituent is any one of halogen, C1-C5 chain alkyl, C6-C18 aryl, C3-C18 heteroaryl, C1-C5 silylalkyl.
  6. 6. The polycyclic aromatic compound of claim 1 or 4 wherein each R 1 、R 2 is independently one of a substituted or unsubstituted C1-C10 chain alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C1-C10 silylalkyl, a substituted or unsubstituted C1-C10 alkoxy, a substituted or unsubstituted C6-C20 aryl, a substituted or unsubstituted C3-C20 heteroaryl, a substituted or unsubstituted C6-C20 aryloxy; The substitution of each of the substituted or unsubstituted groups described in R 1 、R 2 means that each is independently substituted with one group selected from deuterium, halogen, cyano, C1-C5 chain alkyl, C1-C5 alkoxy, C3-C5 cycloalkyl, C2-C5 heterocycloalkyl, C1-C5 silylalkyl, C6-C30 aryloxy, C6-C30 arylamino, C6-C30 aryl or C3-C30 heteroaryl.
  7. 7. The polycyclic aromatic compound according to claim 1 or 4, wherein R 1 、R 2 is each independently selected from any of the substituted or unsubstituted groups shown below, representing the attachment site of a group: the above-mentioned substitution of each group, which is substituted or unsubstituted, means that it is independently substituted with one selected from deuterium, halogen, cyano, C1-C5 chain alkyl, C3-C5 cycloalkyl, C6-C20 aryl or C3-C20 heteroaryl.
  8. 8. The polycyclic aromatic compound according to claim 1, having a structure as shown in any one of the following:
  9. 9. The use of the polycyclic aromatic compound according to any one of claims 1-8 as a functional material in an organic electronic device comprising an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet scanner or electronic paper; preferably, the polycyclic aromatic compound is used as a light emitting layer material in an organic electroluminescent device, more preferably as a doping material in a light emitting layer.
  10. 10. An organic electroluminescent device comprising a first electrode, a second electrode, and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layers comprise a light-emitting layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron blocking layer, the light-emitting layer comprises a host material and a doping material, and the doping material comprises at least one polycyclic aromatic compound according to any one of claims 1 to 8.
  11. 11. An electronic device having a display screen or panel comprising the organic electroluminescent device of claim 9.

Description

Organic compound and application thereof Technical Field The invention relates to an organic compound, in particular to a polycyclic aromatic compound, which belongs to the technical field of organic luminescent materials, and also relates to application of the compound in an organic electroluminescent device and the organic electroluminescent device adopting the compound. Background Optoelectronic devices based on organic materials have become increasingly popular in recent years. The OLED device core is a thin film structure containing a plurality of organic functional materials. Common functional organic materials include hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, light-emitting host materials, light-emitting guests (dyes), and the like. When energized, electrons and holes are injected, transported to the light emitting region, respectively, and recombined therein, thereby generating excitons and emitting light. Various organic materials have been developed, and various device structures with specific designs are combined, so that carrier mobility can be improved, carrier balance can be regulated, electroluminescent efficiency can be broken through, and device attenuation can be delayed. For quantum mechanical reasons, common fluorescent emitters emit light mainly using singlet excitons generated when electrons and holes are combined, and are still widely used in various OLED products. Some metal complexes, such as iridium complexes, can emit light using both triplet and singlet excitons, known as phosphorescent emitters, and can have energy conversion efficiencies up to four times greater than conventional fluorescent emitters. The thermal excitation delayed fluorescence (TADF) technique can achieve higher luminous efficiency by promoting transition of triplet excitons to singlet excitons, and still effectively utilizing triplet excitons without using a metal complex. The thermal excitation sensitized fluorescence (TASF) technology adopts a material with TADF property, and sensitizes the luminophor in an energy transfer mode, so that higher luminous efficiency can be realized. In 2016, the professor Takuji Hatakeyama of japan proposed a material design strategy based on TADF (THERMALLYACTIVATED DELAYED Fluorescence ) of the B-N resonance type (adv. The material is composed of boron atoms, nitrogen atoms and a plurality of benzene rings, presents a rigid polycyclic aromatic hydrocarbon structure and has higher fluorescence quantum yield. In particular, compared with the traditional blue fluorescent dye, the fluorescent dye has the advantages of narrower spectrum, higher color purity and obvious advantages. However, due to its rigid structure, which is particularly planar, molecular packing and exciton annihilation are easily caused, resulting in a severe efficiency roll-off. Therefore, the organic electroluminescent material has great room for improvement in terms of luminous performance. As OLED products continue to enter the market, there is an increasing demand for the performance of such products. The currently used OLED materials and device structures cannot completely solve the problems of OLED product efficiency, lifetime, cost, etc. There is a need in the art to develop a greater variety of higher performance organic materials for use in organic electroluminescent devices, which result in better light emitting efficiency, longer lifetime, etc. Disclosure of Invention Aiming at the defects of the prior art, the invention aims to provide an organic compound and application thereof, in particular to a polycyclic aromatic compound and application thereof. To achieve the purpose, the invention adopts the following technical scheme: in a first aspect, the present invention provides a polycyclic aromatic compound having a structure as shown in formula (1): in the formula (1), the ring A and the ring B are respectively and independently one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; Y is one of O, S, NAr 1; ar 1 is one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, ar 1 is connected or disconnected with ring A, ar 1 is connected or disconnected with ring B; M represents one of a single bond and O, S; R 1、R2 is independently selected from one of substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silylalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 arylamino, and substituted or unsubstituted C3-C30 heteroarylamino; U 1、U2、U3、U4 are each independently CR 01 or N; R 01 is independently