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CN-122010988-A - Organic compound and application thereof

CN122010988ACN 122010988 ACN122010988 ACN 122010988ACN-122010988-A

Abstract

The invention provides a polycyclic aromatic compound and application thereof, wherein the polycyclic aromatic compound has a structure shown in a formula (1). The polycyclic aromatic compound provided by the invention has good stability and spatial configuration, and excellent carrier transmission efficiency, and can be used as a material of a luminescent layer for an organic electroluminescent device, so that the service life of the device can be effectively prolonged, and the luminous efficiency can be improved.

Inventors

  • DENG YAWEN
  • LI YILANG
  • LI GUOMENG

Assignees

  • 北京鼎材科技股份有限公司

Dates

Publication Date
20260512
Application Date
20241030

Claims (10)

  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 selected from one of an unsubstituted C6-C30 aromatic ring or an R 0 substituted C3-C30 heteroaromatic ring or an unsubstituted C 0 substituted C3-C30 heteroaromatic ring; R 0 is independently selected from one or two of deuterium, R A , halogen, cyano, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkyl silicon base, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl and C6-C30 aryl, adjacent two R 0 are connected or not connected, and each R 0 is independently connected with the adjacent ring structure or is connected through a chemical bond to form a ring; X 1 、X 2 、X 3 、X 4 、X 5 、X 6 、X 7 、X 8 、X 9 、X 10 Each independently selected from N or CR 1 , and at least one of which is selected from N, wherein two adjacent R 1 are connected in a ring or not; R 2 represents a substituent group monosubstituted to the maximum allowable number; R 1 、R 2 is each independently selected from one of hydrogen, R A , halogen, cyano, unsubstituted or R 01 substituted C1-C20 straight or branched alkyl, unsubstituted or R 01 substituted C3-C20 cycloalkyl, unsubstituted or R 01 substituted C2-C20 alkenyl, unsubstituted or R 01 substituted C3-C30 heteroaryl, unsubstituted or R 01 substituted C6-C30 aryl; R 01 is independently selected from one or two of deuterium, halogen, cyano, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkyl silicon base, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl and C6-C30 aryl, two adjacent R 01 are connected or not connected, and each R 01 is independently disconnected with an adjacent ring structure or connected through a chemical bond to form a ring; At least one of the R 0 、R 1 、R 2 is a substituted or unsubstituted C6-C60 aryl group with R A ,R A being T1<2.40eV, a substituted or unsubstituted C3-C60 heteroaryl group with T1<2.40eV, wherein each substituent of the substitution is independently selected from deuterium, halogen, cyano, amino, C1-C20 straight or branched alkyl, C2-C20 alkenyl, C1-C20 alkoxy, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, or a combination of two; Y 1 and Y 2 are each independently selected from a single bond, O or S, n 1 and n 2 are each independently 0 or 1, and n 1 +n 2 is 1 or 2.
  2. 2. The polycyclic aromatic compound according to claim 1, wherein in formula (1), at least one of R 0 、R 1 、R 2 is selected from R A , said R A being one of substituted or unsubstituted C13-C40 aryl with T1<2.40eV, substituted or unsubstituted C12-C40 heteroaryl with T1<2.40 eV; preferably, R A is selected from one of the following substituted or unsubstituted groups, — represents the attachment site of the group: Wherein the substituted substituents are each independently selected from one or a combination of two of deuterium, halogen, cyano, amino, C1-C20 straight or branched alkyl, C2-C20 alkenyl, C1-C20 alkoxy, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, preferably the substituted substituents are each independently selected from one or a combination of two of deuterium, halogen, cyano, amino, C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, C2-C10 heterocycloalkyl, C6-C20 aryl, C3-C20 heteroaryl.
  3. 3. The polycyclic aromatic compound according to claim 1 or 2, characterized by a structure selected from the group consisting of the following formula (1-1), formula (1-2), formula (1-3), formula (1-4) and formula (1-5): wherein the definition range of X 2 -X 10 、R 2 is the same as that in formula (1); Y 1 and Y 2 are each independently selected from O or S; Each Z 2 、Z 3 、Z 4 、Z 5 、Z 6 、Z 7 、Z 8 is independently selected from N or CR 3 ; R 3 is independently selected from one or two of hydrogen, deuterium, R A , halogen, cyano, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkyl silicon base, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl and C6-C30 aryl, and two adjacent R 3 are connected in a ring or not; y 3 is selected from O or S.
  4. 4. The polycyclic aromatic compound according to claim 1 or 3, wherein at least one of X 2 -X 10 is selected from N and up to four are selected from N and the remainder from CR 1 , preferably at least one of said X 3 、X 5 、X 8 、X 10 is selected from N and the remainder from CR 1 , further preferably at most two of said X 3 、X 5 、X 8 、X 10 are selected from N and the remainder from CR 1 , further preferably X 3 and/or X 5 are selected from N, X 8 、X 10 is selected from N or CR 1 and the remainder from CR 1 , most preferably X 3 and/or X 5 are selected from N, X 2 、X 4 is selected from CH, X 8 、X 10 is selected from N or CR 1 and the remainder from CR 1 ; Each R 1 is independently selected from one of hydrogen, R A , halogen, cyano, C1-C10 straight or branched alkyl which is unsubstituted or substituted by R 01 , C3-C10 cycloalkyl which is unsubstituted or substituted by R 01 , C3-C30 heteroaryl which is unsubstituted or substituted by R 01 , C6-C30 aryl which is unsubstituted or substituted by R 01 , each R 01 is independently selected from one of deuterium, halogen, cyano, C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylsilyl, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryl, C6-C30 aryl; Preferably, each R 1 is independently selected from hydrogen, R A , halogen, cyano or any of the following groups— represents the attachment site of the group:
  5. 5. The polycyclic aromatic compound according to claim 3, wherein at most one of Z 2 ～Z 8 is selected from N and the remainder are selected from CR 3 , preferably Z 2 ～Z 8 are each independently selected from CR 3 ; Each R 3 is independently selected from one or a combination of two of hydrogen, deuterium, R A , halogen, cyano, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C3-C30 heteroaryl, C6-C30 aryl; Preferably, each R 3 is independently selected from hydrogen, R A , halogen, cyano or any of the following groups— represents the attachment site of the group:
  6. 6. The polycyclic aromatic compound of claim 1 or 3, wherein each R 2 is independently selected from one of hydrogen, R A , halogen, cyano, unsubstituted or R 01 substituted C1-C10 straight or branched alkyl, unsubstituted or R 01 substituted C3-C10 cycloalkyl, unsubstituted or R 01 substituted C3-C30 heteroaryl, unsubstituted or R 01 substituted C6-C30 aryl, R 01 is independently selected from one of deuterium, halogen, cyano, C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylsilyl, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryl, C6-C30 aryl; Preferably, each R 2 is independently selected from hydrogen, R A , halogen, cyano or any of the following groups— represents the attachment site of the group:
  7. 7. The polycyclic aromatic compound according to any one of claims 1-6, wherein the aromatic compound has any one of the following structures:
  8. 8. the use of the polycyclic aromatic compound according to any one of claims 1-7 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.
  9. 9. 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 7.
  10. 10. 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 belongs to the technical field of organic luminescent materials, in particular relates to a polycyclic aromatic compound, and also relates to application of the compound in an organic electroluminescent device and the organic electroluminescent device adopting the compound. Background The inherent flexibility of organic materials makes them very suitable for fabrication on flexible substrates, which can be designed to produce aesthetically pleasing and cool optoelectronic products, as desired, with no comparable advantages over inorganic materials. Examples of such organic optoelectronic devices include Organic Light Emitting Diodes (OLEDs), organic field effect transistors, organic photovoltaic cells, organic sensors, and the like. Among them, OLED has been developed particularly rapidly, and has been commercially successful in the field of information display. OLED can provide three colors of red, green and blue with high saturation, and the full-color display device manufactured by the OLED does not need extra backlight source, and has the advantages of colorful, light, thin, soft and the like. 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 to improve carrier mobility, regulate carrier balance, break through electroluminescent efficiency, and delay device decay. In 2016, the professor Takuji Hatakeyama of japan proposed a material design strategy based on TADF (THERMALLY ACTIVATED 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. Therefore, there is a need in the art to develop a wider variety of organic materials with higher performance, which are applied to organic electroluminescent devices, so that the devices have better light emitting effect, longer lifetime, etc. Disclosure of Invention Aiming at the defects of the prior art, the invention aims to provide an aromatic compound and application thereof, in particular to a polycyclic aromatic compound and application thereof. According to the polycyclic aromatic compound provided by the invention, N atoms are introduced into a parent nucleus (such as a BN parent nucleus), and meanwhile, specific low triplet fragment structural groups are introduced into the periphery, so that on one hand, the HOMO energy level of the material can be reduced, hole capturing is reduced, the proportion of holes and electrons in the device is more balanced, and the efficiency and the service life are improved. On the other hand, the low triplet state fragment can reduce the triplet state energy level of the molecule, which is beneficial to further improving the service life of the device. The polycyclic aromatic compounds provided by the invention are very suitable for application to OLEDs and improve device performance through smart molecular design/device design. 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 according to formula (1): In the formula (1), the ring A and the ring B are respectively and independently selected from one of an unsubstituted C6-C30 aromatic ring or an R 0 substituted C3-C30 heteroaromatic ring or an unsubstituted C 0 substituted C3-C30 heteroaromatic ring; R 0 is independently selected from one or two of deuterium, R A, halogen, cyano, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkyl silicon base, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 he