Methyl radical compound and organic electroluminescent device

Abstract

The invention relates to the technical field of organic electroluminescent materials, in particular to a methyl radical compound and an organic electroluminescent device. According to the methyl free radical compound provided by the invention, a structural unit with a conjugation characteristic and electron donor / acceptor capability is introduced into a molecular skeleton, and the electron distribution and configuration rigidity of molecules are accurately regulated and controlled, so that the dual-state spin characteristic is maintained, meanwhile, the excited state non-radiative attenuation is effectively inhibited, and the photoinduced or electroluminescent efficiency of the methyl free radical compound is improved; meanwhile, the methyl free radical compound contains an aza-aromatic group with a stable free radical center and is connected to a push-pull electronic structure through a pi-conjugate bridging unit, the luminescence performance is adjusted through the charge transfer effect, and the methyl free radical compound is suitable for application scenes such as high-resolution display, biological imaging and low-energy-consumption infrared communication.

Description

Technical Field

[0002] This invention relates to the field of organic electroluminescent materials technology, and more particularly to a methyl radical compound and an organic electroluminescent device. Background Technology

[0003] Organic light-emitting materials (OLEDs) have wide applications in display and lighting fields due to their flexibility, low cost, and color tunability. Among them, organic radical materials, with their unique electronic structure, exhibit a series of excellent optoelectronic properties and have attracted increasing attention. Unlike traditional closed-shell fluorescent or phosphorescent materials, organic radical molecules possess an unpaired electron, and their ground and excited states are typically dual states, theoretically capable of achieving 100% internal quantum efficiency, thus providing a new strategy for the design of high-efficiency organic electroluminescent devices. Stable luminescent radicals have successfully achieved electroluminescence in the near-infrared band, showing potential application value in cutting-edge technologies such as bioimaging and information communication. However, the types of luminescent radical molecules are currently limited, and the synthesis yield is low. Therefore, developing high-performance novel luminescent radical materials remains a key challenge in this field.

[0004] Therefore, there is an urgent need to develop free radical luminescent materials with novel structures, high luminous efficiency, and good stability to meet the higher requirements of next-generation organic optoelectronic devices for the performance of functional materials. Summary of the Invention

[0005] In view of this, the purpose of the present invention is to provide a methyl radical compound and an organic electroluminescent device, wherein the methyl radical compound has high luminous efficiency and good luminous stability.

[0006] To achieve the above-mentioned objectives, the present invention provides the following technical solution: This invention provides a methyl radical compound having the structure shown in Formula 1: Formula 1; In Equation 1, X1, X1 1 X2, X2 1 X2 2 X2 3 X3, X3 1 X3 2 and X3 3 Independently, it consists of hydrogen atom, deuterium atom, halogen, cyano group, unsubstituted alkyl group, and R. 1 Substituted alkyl groups, unsubstituted alkoxy groups, R 1 Substituted alkoxy groups, unsubstituted alkenyl groups, R 1 Substituted alkenyl groups, unsubstituted alkynyl groups, R 1 Substituted alkynyl group, unsubstituted aryl group, R 1Substituted aryl, unsubstituted heteroaryl, or R 1 Substituted heteroaryl groups; R1, R2, and R3 are independently hydrogen atoms, deuterium atoms, halogens, cyano groups, -NO2, and -N(R) atoms. 1 )2、-OR 1 -SR 1 -C(=O)R 1 -P(=O)R 1 、-Si(R 1 3. Unsubstituted alkoxy groups, R 1 Substituted alkoxy groups, unsubstituted alkyl groups, R 1 Substituted alkyl groups, unsubstituted alkenyl groups, R 1 Substituted alkenyl groups, unsubstituted alkynyl groups, R 1 Substituted alkynyl group, unsubstituted aryl group, R 1 Substituted aryl, unsubstituted heteroaryl, or R 1 Substituted heteroaryl groups; The X1, X1 1 X2, X2 1 X2 2 X2 3 X3, X3 1 X3 2 and X3 3 Chinese R 1 Substituted alkyl, R 1 Substituted alkoxy groups, R 1 Substituted alkenyl, R 1 Substituted alkynyl group, R 1 Substituted aryl and R 1 Substituted heteroaryl groups, the N(R) 1 )2、-OR 1 -SR 1 -C(=O)R 1 -P(=O)R 1 and -Si(R 1 )3 in R 1 And R in R1, R2 and R3 1 Substituted alkoxy groups, R 1 Substituted cycloalkyl, R 1 Substituted alkenyl, R 1 Substituted alkynyl group, R 1 Substituted aryl and R 1 The substituted heteroaryl groups are all independently hydrogen atoms, deuterium atoms, halogens, cyano groups, -NO2, -N(R) 2 )2、-OR 2 -SR 2 -C(=O)R 2 -P(=O)R2 、-Si(R 2 3. R 2 Substituted alkyl, R 2 Substituted alkenyl, R 2 Substituted alkynyl group, R 2 Substituted aromatic hydrocarbon groups or R 2 Substituted aromatic heterocyclic groups; The -NO2, -N(R) 2 )2、-OR 2 -SR 2 -C(=O)R 2 -P(=O)R 2 and -Si(R 2 )3 in R 2 and the R 2 Substituted alkenyl, R 2 Substituted alkynyl group, R 2 Substituted aromatic hydrocarbon groups and R 2 R in substituted aromatic heterocyclic groups 2 Each of these can be independently composed of a hydrogen atom, a deuterium atom, a halogen, a cyano group, an alkyl group, an alkoxy group, a cycloalkyl group, an alkenyl group, an aryl group, or a heteroaryl group.

[0007] Preferably, X1, X1 1 X2, X2 1 X2 2 X2 3 X3, X3 1 X3 2 or X3 3 middle, The unsubstituted alkyl or R 1 The substituted alkyl group has 1 to 20 carbon atoms in the alkyl moiety. The unsubstituted alkoxy or R 1 The number of carbon atoms in the alkoxy group of the substituted alkoxy group is 1 to 20; The unsubstituted alkenyl or R 1 The number of carbon atoms in the substituted alkenyl group is 2 to 20 independently; The unsubstituted alkynyl group or R 1 In substituted alkynyl groups, the number of carbon atoms in the alkynyl group is 2 to 20; The unsubstituted aryl or R 1 The number of carbon atoms in the substituted aryl group is 6 to 40; The unsubstituted heteroaryl or R 1 The number of carbon atoms in the substituted heteroaryl groups is 6 to 40; The R 1 Substituted alkyl, R1 Substituted alkoxy groups, R 1 Substituted alkenyl, R 1 Substituted alkynyl group, R 1 Substituted aryl and R 1 R in substituted heteroaryl groups 1 The number of substitutions is ≥1.

[0008] Preferably, the unsubstituted alkyl group includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, 2-methylhexyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, 3-methylheptyl, n-nonyl, n-decyl, hexadecyl, octadecyl, eicosyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, or cyclooctyl. The unsubstituted alkoxy group is an unsubstituted alkyl group that is substituted by ≥1 alkoxy group; The unsubstituted alkenyl groups include vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanyl, eicosene, 2-ethylhexenyl, allyl, or cyclohexenyl. The unsubstituted alkynyl group includes ethynyl, isopropynyl, butynyl, penynyl, hexynyl, hepynyl, ocynyl, nonynyl, or decynyl; The unsubstituted aryl group includes phenyl, biphenyl, triphenyl, tetraphenyl, or pentaphenyl; The unsubstituted heteroaryl groups include benzothiophenecarbazolyl, benzofuranocarbazolyl, benzofluorenocarbazolyl, benzoanthrayl, benzophenanthryl, fluorenyl, spirobisfluorenyl, triazine, dibenzofuranyl, dibenzothiophene, carbazolyl, N-phenylcarbazolyl, indocarbazolyl, benzimidazolyl, diphenyl-benzimidazolyl, diphenyl-oxadiazolyl, diphenylboryl, triphenylphosphoxy, diphenylphosphoxy, triphenylsilyl, or tetraphenylsilyl.

[0009] Preferably, of R1, R2 and R3, The unsubstituted alkoxy group and R 1 The number of carbon atoms in the alkoxy moiety of the substituted alkoxy group is independently 1 to 20; The unsubstituted alkyl and R 1 The cyclic alkyl moiety in the substituted alkyl group has 3 to 10 carbon atoms independently; The unsubstituted alkenyl and R 1The number of carbon atoms in the alkenyl moiety of the substituted alkenyl group is independently 2 to 20; The unsubstituted alkynyl group and R 1 The number of carbon atoms in the substituted alkynyl group is independently 2 to 20; The unsubstituted aryl and R 1 The number of carbon atoms in the aryl moiety of the substituted aryl group is 6 to 40; The unsubstituted heteroaryl or R 1 The number of carbon atoms in the heteroaryl moiety of the substituted heteroaryl group is 5 to 40; The R 1 Substituted alkoxy groups, R 1 Substituted cycloalkyl, R 1 Substituted alkenyl, R 1 Substituted alkynyl group, R 1 Substituted aryl and R 1 R in substituted heteroaryl groups 1 The number of elements is ≥1.

[0010] Preferably, the unsubstituted alkyl group includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, 2-methylhexyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, 3-methylheptyl, n-nonyl, n-decyl, hexadecyl, octadecyl, eicosyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, or cyclooctyl. The unsubstituted alkoxy group is an unsubstituted alkyl group that is substituted by ≥1 alkoxy group; The unsubstituted alkenyl groups include vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanyl, eicosene, 2-ethylhexenyl, allyl, or cyclohexenyl. The unsubstituted alkynyl group includes ethynyl, isopropynyl, butynyl, penynyl, hexynyl, hepynyl, ocynyl, nonynyl, or decynyl; The unsubstituted aryl group includes phenyl, biphenyl, triphenyl, tetraphenyl, or pentaphenyl; The unsubstituted heteroaryl groups include benzothiophenecarbazolyl, benzofuranocarbazolyl, benzofluorenocarbazolyl, benzoanthrayl, benzophenanthryl, fluorenyl, spirobisfluorenyl, triazine, dibenzofuranyl, dibenzothiophene, carbazolyl, N-phenylcarbazolyl, indocarbazolyl, benzimidazolyl, diphenyl-benzimidazolyl, diphenyl-oxadiazolyl, diphenylboryl, triphenylphosphoxy, diphenylphosphoxy, triphenylsilyl, or tetraphenylsilyl.

[0011] Preferably, the R 2 The number of carbon atoms in the alkyl moiety of the substituted alkyl group is 1 to 20; The R 2 The number of carbon atoms in the alkenyl moiety of the substituted alkenyl group is 2 to 20; The R 2 The number of carbon atoms in the substituted alkynyl group is 2 to 20; The R 2 The number of carbon atoms in the aromatic hydrocarbon group of the substituted aromatic hydrocarbon group is 6 to 40; The R 2 The number of carbon atoms in the aromatic heterocyclic group of the substituted aromatic heterocyclic group is 5 to 40.

[0012] Preferably, the R 2 middle, The alkyl group is a C1~C20 alkyl group; The alkoxy group is a C1~C20 alkoxy group; The cycloalkyl group is a C3~C10 cycloalkyl group; The alkenyl group is a C2~C20 alkenyl group; The alkynyl group is a C2~C20 alkynyl group; The aryl group is a C6~C40 alkynyl group; The heteroaryl group is a C5~C40 heteroaryl group.

[0013] Preferably, R1, R2, and R3 independently have any of the structures shown in formulas Ar-1 to Ar-34: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , or .

[0014] Preferably, any R in formulas Ar-1 to Ar-34 1 The following are all independent compounds: phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, perylene, fluoranthyl, benzo[a]fluoranthyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, azophenyl, terphenyl, tetraphenyl, pentaphenyl, trimerphenyl, fluorenyl, spirobisfluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorenyl, cis or trans monobenzo[a]fluorenyl, cis or trans dibenzo[a]fluorenyl, trimerinyl, isotrimericininyl, spirotrimericininyl, spiroisotrimericininyl, furanyl, Benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, benzothiophenecarbazoyl, pyrroleyl, indolyl, isoindolyl, carbazoyl, indolocarbazoyl, indocarbazoyl, pyridyl, bipyridyl, terpyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, phenothiazinyl, phenotoxazinyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazinyl Azolyl, naphthemidazole, phenanthrenemidazole, pyridinidazole, pyrazinidazole, quinoxalinidazole, oxazolyl, benzoxazolyl, benzoxadiazolyl, naphthemidazole, anthraquinoxazolyl, phenanthrenemidazole, isoxazolyl, thiazolyl, isothiazolyl, benzothiazolyl, benzothiadiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, quinazolinyl, azafluorenyl, diazaanthrayl, diazapyrene, tetraazaperyl, diazanaphthyl, pyrazinyl, phenazinyl, phenoxazinyl, phenthiazolyl Azinyl, fluorescein cycloyl, naphthidyl, azacarbazolyl, benzocarbaolinyl, phenanthrolinel, triazolyl, benzotriazolyl, oxadiazolyl, thiadiazolyl, triazinyl, tetrazolyl, tetraazinyl, purinyl, pteridyl, inazinyl, benzothiadiazolyl, pyridopyrroleyl, pyridotriazolyl, xanthonyl, benzofuranocarbazolyl, benzofluorenocarbazolyl, N-phenylcarbazolyl, diphenyl-benzimidazolyl, diphenyl-oxadiazolyl, diphenylboryl, triphenylphosphoxy, diphenylphosphoxy, triphenylsilyl or tetraphenylsilyl.

[0015] The present invention also provides the application of the methyl radical compound described in the above technical solution in organic electroluminescent devices.

[0016] This invention provides a methyl radical compound having the structure shown in Formula 1: Formula 1; In Equation 1, X1, X1 1 X2, X2 1 X2 2 X2 3 X3, X3 1 X3 2 and X3 3 Independently, it consists of hydrogen atom, deuterium atom, halogen, cyano group, unsubstituted alkyl group, and R. 1 Substituted alkyl groups, unsubstituted alkoxy groups, R 1 Substituted alkoxy groups, unsubstituted alkenyl groups, R 1 Substituted alkenyl groups, unsubstituted alkynyl groups, R 1 Substituted alkynyl group, unsubstituted aryl group, R 1 Substituted aryl, unsubstituted heteroaryl, or R 1 Substituted heteroaryl groups; R1, R2, and R3 are independently hydrogen atoms, deuterium atoms, halogens, cyano groups, -NO2, and -N(R) atoms. 1 )2、-OR 1 -SR 1 -C(=O)R 1 -P(=O)R 1 、-Si(R 1 3. Unsubstituted alkoxy groups, R 1 Substituted alkoxy groups, unsubstituted alkyl groups, R 1 Substituted alkyl groups, unsubstituted alkenyl groups, R 1 Substituted alkenyl groups, unsubstituted alkynyl groups, R 1 Substituted alkynyl group, unsubstituted aryl group, R 1 Substituted aryl, unsubstituted heteroaryl, or R 1 Substituted heteroaryl groups; The X1, X1 1 X2, X2 1 X2 2 X2 3 X3, X3 1 X3 2 and X3 3 Chinese R 1 Substituted alkyl, R 1 Substituted alkoxy groups, R 1 Substituted alkenyl, R 1 Substituted alkynyl group, R1 Substituted aryl and R 1 Substituted heteroaryl groups, the N(R) 1 )2、-OR 1 -SR 1 -C(=O)R 1 -P(=O)R 1 and -Si(R 1 )3 in R 1 And R in R1, R2 and R3 1 Substituted alkoxy groups, R 1 Substituted cycloalkyl, R 1 Substituted alkenyl, R 1 Substituted alkynyl group, R 1 Substituted aryl and R 1 The substituted heteroaryl groups are all independently hydrogen atoms, deuterium atoms, halogens, cyano groups, -NO2, -N(R) 2 )2、-OR 2 -SR 2 -C(=O)R 2 -P(=O)R 2 、-Si(R 2 3. R 2 Substituted alkyl, R 2 Substituted alkenyl, R 2 Substituted alkynyl group, R 2 Substituted aromatic hydrocarbon groups or R 2 Substituted aromatic heterocyclic groups; The -NO2, -N(R) 2 )2、-OR 2 -SR 2 -C(=O)R 2 -P(=O)R 2 and -Si(R 2 )3 in R 2 and the R 2 Substituted alkenyl, R 2 Substituted alkynyl group, R 2 Substituted aromatic hydrocarbon groups and R 2 R in substituted aromatic heterocyclic groups 2 Each of these can be independently composed of a hydrogen atom, a deuterium atom, a halogen, a cyano group, an alkyl group, an alkoxy group, a cycloalkyl group, an alkenyl group, an aryl group, or a heteroaryl group.

[0017] The methyl radical compound of this invention introduces structural units with conjugation properties and electron donor / acceptor capabilities into the molecular skeleton. By precisely controlling the electron distribution and configurational rigidity of the molecule, it effectively suppresses non-radiative decay of the excited state while maintaining the dual-state spin characteristics, thereby improving its photoluminescence or electroluminescence efficiency. At the same time, the methyl radical compound contains a nitrogen-containing aromatic group with a stable radical center, which is connected to the push-pull electronic structure through π-conjugated bridging units. The luminescence performance is adjusted through charge transfer, making it suitable for applications such as high-resolution displays, bio-imaging, and low-energy infrared communication. Attached Figure Description

[0018] Figure 1 The ultraviolet absorption spectra (UV-Vis) and room temperature fluorescence spectra (PL) of compounds 1-2 and 1-9 are shown. Figure 2 EPR plots for compounds 1-2 and 1-9; Figure 3 The electroluminescence spectrum of the organic electroluminescent device described in Example 1 at 13V; Figure 4 The external quantum efficiency-voltage characteristic curve of the organic electroluminescent device described in Example 1 is shown. Figure 5 The voltage-current density and voltage-radiance characteristic curves of the organic electroluminescent device described in Example 1 are shown. Detailed Implementation

[0019] This invention provides a methyl radical compound having the structure shown in Formula 1: Formula 1; In Equation 1, X1, X1 1 X2, X2 1 X2 2 X2 3 X3, X3 1 X3 2 and X3 3 Independently, it consists of hydrogen atom, deuterium atom, halogen, cyano group, unsubstituted alkyl group, and R. 1 Substituted alkyl groups, unsubstituted alkoxy groups, R 1 Substituted alkoxy groups, unsubstituted alkenyl groups, R 1 Substituted alkenyl groups, unsubstituted alkynyl groups, R 1 Substituted alkynyl group, unsubstituted aryl group, R 1 Substituted aryl, unsubstituted heteroaryl, or R 1 Substituted heteroaryl groups; R1, R2, and R3 are independently hydrogen atoms, deuterium atoms, halogens, cyano groups, -NO2, and -N(R) atoms. 1)2、-OR 1 -SR 1 -C(=O)R 1 -P(=O)R 1 、-Si(R 1 3. Unsubstituted alkoxy groups, R 1 Substituted alkoxy groups, unsubstituted alkyl groups, R 1 Substituted alkyl groups, unsubstituted alkenyl groups, R 1 Substituted alkenyl groups, unsubstituted alkynyl groups, R 1 Substituted alkynyl group, unsubstituted aryl group, R 1 Substituted aryl, unsubstituted heteroaryl, or R 1 Substituted heteroaryl groups; The X1, X1 1 X2, X2 1 X2 2 X2 3 X3, X3 1 X3 2 and X3 3 Chinese R 1 Substituted alkyl, R 1 Substituted alkoxy groups, R 1 Substituted alkenyl, R 1 Substituted alkynyl group, R 1 Substituted aryl and R 1 Substituted heteroaryl groups, the N(R) 1 )2、-OR 1 -SR 1 -C(=O)R 1 -P(=O)R 1 and -Si(R 1 )3 in R 1 And R in R1, R2 and R3 1 Substituted alkoxy groups, R 1 Substituted cycloalkyl, R 1 Substituted alkenyl, R 1 Substituted alkynyl group, R 1 Substituted aryl and R 1 The substituted heteroaryl groups are all independently hydrogen atoms, deuterium atoms, halogens, cyano groups, -NO2, -N(R) 2 )2、-OR 2 -SR 2 -C(=O)R 2 -P(=O)R 2 、-Si(R 2 3. R 2 Substituted alkyl, R 2 Substituted alkenyl, R 2 Substituted alkynyl group, R2 Substituted aromatic hydrocarbon groups or R 2 Substituted aromatic heterocyclic groups; The -NO2, -N(R) 2 )2、-OR 2 -SR 2 -C(=O)R 2 -P(=O)R 2 and -Si(R 2 )3 in R 2 and the R 2 Substituted alkenyl, R 2 Substituted alkynyl group, R 2 Substituted aromatic hydrocarbon groups and R 2 R in substituted aromatic heterocyclic groups 2 Each of these can be independently composed of a hydrogen atom, a deuterium atom, a halogen, a cyano group, an alkyl group, an alkoxy group, a cycloalkyl group, an alkenyl group, an aryl group, or a heteroaryl group.

[0020] In this invention, X1, X1 1 X2, X2 1 X2 2 X2 3 X3, X3 1 X3 2 or X3 3 In this context, the halogen is preferably a fluorine atom, chlorine atom, bromine atom, or iodine atom; the unsubstituted alkyl or R 1 The substituted alkyl group preferably has 1 to 20 carbon atoms in the alkyl moiety; the unsubstituted alkoxy group or R 1 The substituted alkoxy group preferably has 1 to 20 carbon atoms in the alkoxy moiety; the unsubstituted alkenyl or R 1 The number of carbon atoms in the substituted alkenyl group is preferably 2 to 20; the unsubstituted alkynyl group or R 1 The number of carbon atoms in the substituted alkynyl group is preferably 2 to 20; the unsubstituted aryl or R 1 The substituted aryl group preferably has 6 to 40 carbon atoms, with each aryl group having its own number of carbon atoms; the unsubstituted heteroaryl group or R 1 The number of carbon atoms in the substituted heteroaryl group is preferably 6 to 40; the R 1 Substituted alkyl, R 1 Substituted alkoxy groups, R 1 Substituted alkenyl, R 1 Substituted alkynyl group, R 1 Substituted aryl and R 1 R in substituted heteroaryl groups 1The number of substitutions is preferably ≥1. In this invention, the unsubstituted alkyl group preferably includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, 2-methylhexyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, 3-methylheptyl, n-nonyl, n-decyl, hexadecyl, octadecyl, eicosyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethyl Cyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, or cyclooctyl; the unsubstituted alkoxy group is preferably an unsubstituted alkyl group substituted by ≥1 alkoxy group; the unsubstituted alkenyl group preferably includes vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, and undecenyl. Dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosene, 2-ethylhexenyl, allyl, or cyclohexenyl; the unsubstituted alkynyl group preferably includes ethynyl, isopropynyl, butynyl, pentylyl, hexynyl, heptylyl, octylyl, nonynyl, or decynyl; the unsubstituted aryl group preferably includes phenyl, biphenyl, terphenyl, tetraphenyl, or pentaphenyl; Unsubstituted heteroaryl groups preferably include benzothiophenecarbazolyl, benzofuranocarbazolyl, benzofluorenocarbazolyl, benzoanthrayl, benzophenanthryl, fluorenyl, spirobisfluorenyl, triazine, dibenzofuranyl, dibenzothiophene, carbazolyl, N-phenylcarbazolyl, indocarbazolyl, benzimidazolyl, diphenyl-benzimidazolyl, diphenyl-oxadiazolyl, diphenylboryl, triphenylphosphoxy, diphenylphosphoxy, triphenylsilyl, or tetraphenylsilyl.

[0021] In this invention, among R1, R2, and R3, the halogen is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; the unsubstituted alkoxy group and R... 1 The number of carbon atoms in the alkoxy moiety of the substituted alkoxy group is preferably 1 to 20; the unsubstituted alkyl group and R 1 The substituted alkyl group preferably has 3 to 10 carbon atoms in the alkyl moiety; the unsubstituted alkenyl group and R 1 The number of carbon atoms in the alkenyl moiety of the substituted alkenyl group is preferably 2 to 20; the unsubstituted alkynyl group and R 1 The number of carbon atoms in the substituted alkynyl group is preferably 2 to 20; the unsubstituted aryl group and R 1 The substituted aryl group preferably has 6 to 40 carbon atoms in the aryl moiety; the unsubstituted heteroaryl group or R 1 The number of carbon atoms in the heteroaryl moiety of the substituted heteroaryl group is preferably 5 to 40; the R 1Substituted alkoxy groups, R 1 Substituted alkyl, R 1 Substituted alkenyl, R 1 Substituted alkynyl group, R 1 Substituted aryl and R 1 R in substituted heteroaryl groups 1 The number of alkyl groups is preferably ≥1. In this invention, the unsubstituted alkyl group preferably includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, 2-methylhexyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, 3-methylheptyl, n-nonyl, n-decyl, hexadecyl, octadecyl, eicosyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethyl Cyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, or cyclooctyl; the unsubstituted alkoxy group is preferably an unsubstituted alkyl group substituted by ≥1 alkoxy group; the unsubstituted alkenyl group preferably includes vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, and undecenyl. Dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosene, 2-ethylhexenyl, allyl, or cyclohexenyl; the unsubstituted alkynyl group preferably includes ethynyl, isopropynyl, butynyl, pentylyl, hexynyl, heptylyl, octylyl, nonynyl, or decynyl; the unsubstituted aryl group preferably includes phenyl, biphenyl, terphenyl, tetraphenyl, or pentaphenyl; Unsubstituted heteroaryl groups preferably include benzothiophenecarbazolyl, benzofuranocarbazolyl, benzofluorenocarbazolyl, benzoanthrayl, benzophenanthryl, fluorenyl, spirobisfluorenyl, triazine, dibenzofuranyl, dibenzothiophene, carbazolyl, N-phenylcarbazolyl, indocarbazolyl, benzimidazolyl, diphenyl-benzimidazolyl, diphenyl-oxadiazolyl, diphenylboryl, triphenylphosphoxy, diphenylphosphoxy, triphenylsilyl, or tetraphenylsilyl.

[0022] In this invention, the R 2 The number of carbon atoms in the alkyl moiety of the substituted alkyl group is preferably 1 to 20; the R 2 The number of carbon atoms in the alkenyl moiety of the substituted alkenyl group is preferably 2 to 20; the R 2 The number of carbon atoms in the substituted alkynyl group is preferably 2 to 20; the R 2 The number of carbon atoms in the aromatic hydrocarbon group of the substituted aromatic hydrocarbon group is preferably 6 to 40; the R 2 The number of carbon atoms in the aromatic heterocyclic group of the substituted aromatic heterocyclic group is preferably 5 to 40. In this invention, the R... 2In this context, the alkyl group is preferably a C1-C20 alkyl group, more preferably methyl, ethyl, n-propyl, isopropyl, or n-butyl; the alkoxy group is preferably a C1-C20 alkoxy group, more preferably an unsubstituted alkyl group substituted by ≥1 alkoxy group; the cycloalkyl group is preferably a C3-C10 cycloalkyl group, more preferably cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, or 4-methylcyclohexyl; the alkenyl group is preferably... The aryl group is preferably C2-C20 alkenyl, more preferably vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, or octenyl; the alkynyl group is preferably C2-C20 alkynyl, more preferably ethynyl, isopropynyl, butynyl, or pentylyl; the aryl group is preferably C6-C40 aryl, more preferably phenyl, biphenyl, or terphenyl; the heteroaryl group is preferably C5-C40 heteroaryl, more preferably benzothiophenecarbazolyl, benzofuranocarbazolyl, or benzofluorenecarbazolyl.

[0023] In this invention, R1, R2, and R3 preferably have the structure shown in any of formulas Ar-1 to Ar-34: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , or .

[0024] In this invention, any R1 in formulas Ar-1 to Ar-34 is preferably defined independently as described in the above technical solutions, and more preferably phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, benzo[a]phenanthryl, pyrene, perylene, fluoranthyl, benzo[a]fluoranthyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphylphenyl, terphenyl, tetraphenyl, pentaphenyl, triphenyl, spirobisfluorenyl, dihydrophenanthryl, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorenyl, cis or trans monobenzo[a]indo[a]fluorenyl, cis or trans-dibenzo-indofluorenyl, trimerinyl, isotrimerininyl, spirotrimerininyl, spiroisotrimerininyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, benzothiophenecarbazoyl, pyrroleyl, indolyl, isoindolyl, carbazoyl, indolocarbazoyl, indocarbazoyl, pyridyl, bipyridyl, terpyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl Phenyriazinyl, phenoxazinyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazoleyl, naphzimidazoleyl, phenanthreneimidazoleyl, pyridinimidazoleyl, pyrazinimidazoleyl, quinoxalinimidazoleyl, oxazolyl, benzoxazolyl, benzoxadiazolyl, naphzimidazoleyl, anthraquinoxazolyl, phenanthreneimidazoleyl, isoxazolyl, thiazolyl, isothiazolyl, benzothiazolyl, benzothiadiazolyl, pyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, quinazolinyl, azirmonyl, diazaanthrayl, diazapyrene, tetrazaperyl, diazanaphthyl, pyrazinyl Phenazinyl, phenoxazinyl, phenthiazinyl, fluorescein cycloyl, naphridinyl, azacarbazoyl, benzocarbaolinyl, phenanthrolineyl, triazolyl, benzotriazolyl, oxadiazolyl, thiadiazolyl, triazinyl, tetrazolyl, tetraazinyl, purine, pteridinyl, inazinyl, benzothiadiazolyl, pyridopyrroleyl, pyridotriazolyl, xanthonyl, benzofuranocarbazoyl, benzofluorenocarbazoyl, N-phenylcarbazoyl, diphenyl-benzimidazolyl, diphenyl-oxadiazolyl, diphenylboryl, triphenylphosphoxy, diphenylphosphoxy, triphenylsilyl or tetraphenylsilyl.

[0025] In this invention, the methyl radical compound is preferably any one of compound 1-1 to compound 1-40; .

[0026] In this invention, the methyl radical compound is preferably prepared by using M1 as the reactant through a halogen substitution reaction, Suzuki coupling reaction, or Buchwald-Hartwig coupling reaction known to those skilled in the art.

[0027] In this invention, M1 is specifically (2,4,6-trichloropyrimidinyl)bis(2,4,6-trichlorophenyl)methane, with the following structural formula: .

[0028] In this invention, the method for preparing M1 preferably includes the following steps: The synthesis route is shown in equation a: Formula a; The preferred specific preparation process is as follows: In a 350 mL pressure flask, 2,4,6-trichloro-5-pyrimidinecarboxaldehyde (5.00 g, 23.65 mmol, 1.00 equivalent), 1,3,5-trichlorobenzene (10.73 g, 59.12 mmol, 2.50 equivalent), and trifluoromethanesulfonic acid (70.98 g, 472.98 mmol, 20.00 equivalent) were added sequentially. The flask was then sealed and heated at 180 °C for 24 h. After cooling to room temperature, the reaction mixture was neutralized to pH 7 with an aqueous sodium bicarbonate solution, followed by multiple extractions with dichloromethane. The combined organic phases were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using petroleum ether as eluent to give a white solid M1.

[0029] In this invention, the raw materials for preparing the methyl radical compound are preferably boric acid functionalized compounds corresponding to R1, R2 or R3, or amine derivative compounds corresponding to R1, R2 or R3.

[0030] In this invention, the method for preparing the methyl radical compound preferably includes the following steps: The intermediate product is obtained by mixing the compound M1, the boric acid functionalized compound corresponding to R1, R2 or R3, a palladium catalyst, anhydrous potassium carbonate and a mixed solvent and carrying out a metal-catalyzed coupling reaction. The intermediate product was mixed with a mixed solvent of acetonitrile and tetrahydrofuran, and then a tetrabutylammonium hydroxide methanol solution was added. The mixture was stirred overnight, and tetrachlorobenzoquinone was added to continue the reaction, thereby obtaining the methyl radical compound.

[0031] The present invention involves mixing the compound M1, the boric acid functionalized compound corresponding to R1, R2 or R3, a palladium catalyst, anhydrous potassium carbonate and a mixed solvent to carry out a metal-catalyzed coupling reaction to obtain the intermediate product.

[0032] In this invention, the palladium catalyst is preferably tetra(triphenylphosphine)palladium.

[0033] In this invention, the mixed solvent preferably includes toluene, ethanol and water; the volume ratio of toluene, ethanol and water is preferably (6~12):1:2, more preferably 6:1:2, 7:1:2, 8:1:2, 9:1:2, 10:1:2, 11:1:2 or 12:1:2.

[0034] In this invention, the molar ratio of compound M1, the boric acid functionalized compound corresponding to R1, R2 or R3, palladium catalyst and anhydrous potassium carbonate is preferably (10~30):20:1:80, more preferably (15~25):20:1:80, and most preferably 24:20:1:80.

[0035] The present invention does not impose any special limitation on the amount of the mixed solvent; any amount known to those skilled in the art can be used.

[0036] In this invention, the metal-catalyzed coupling reaction is preferably carried out in a protective atmosphere, preferably a nitrogen atmosphere, and the temperature of the metal-catalyzed coupling reaction is preferably 80~120℃, and the time is preferably 20~35h.

[0037] After the metal-catalyzed coupling reaction is completed, the present invention preferably further includes sequentially cooling to room temperature, pouring the mixture into a saturated NaCl aqueous solution, and extracting three times with dichloromethane (50 mL × 3). The mixture is then purified by drying, vacuum concentration, and silica gel column chromatography (petroleum ether / dichloromethane = 3:1, v / v).

[0038] After obtaining the intermediate product, the present invention further includes mixing the intermediate product with a mixed solvent of acetonitrile and tetrahydrofuran, adding a tetrabutylammonium hydroxide methanol solution, stirring overnight in the dark, adding tetrachlorobenzoquinone, and continuing the reaction to obtain the methyl radical compound.

[0039] In this invention, the volume ratio of acetonitrile to tetrahydrofuran in the mixed solvent of acetonitrile and tetrahydrofuran is preferably 3:1.

[0040] In this invention, the concentration of the tetrabutylammonium hydroxide methanol solution is preferably (0.5~2.5) M, more preferably 1.5 M.

[0041] In this invention, the molar ratio of the intermediate product to tetrabutylammonium hydroxide in the methanol solution is preferably 1:(2~5), more preferably 1:3.

[0042] In this invention, the molar ratio of the intermediate product to tetrachlorobenzoquinone is preferably 1:(2~5), more preferably 1:2.5.

[0043] In this invention, the continued reaction time is preferably 2 to 5 hours, more preferably 4 hours.

[0044] After the continued reaction is completed, the present invention preferably includes post-processing, wherein the post-processing preferably involves filtering the obtained product system through diatomaceous earth, concentrating under reduced pressure, and purifying it by silica gel column chromatography (petroleum ether / dichloromethane = 3:1, v / v).

[0045] Alternatively, in this invention, the method for preparing the methyl radical compound preferably includes the following steps: The intermediate product is obtained by mixing the compound M1, the amine derivatives corresponding to R1, R2 or R3, tris(dibenzylacetone)dipalladium, sodium tert-butoxide, tritert-tert-butylphosphine tetrafluoroborate and toluene and carrying out a metal-catalyzed coupling reaction. The intermediate product was mixed with a mixed solvent of acetonitrile and tetrahydrofuran, and then a tetrabutylammonium hydroxide methanol solution was added. The mixture was stirred overnight, and tetrachlorobenzoquinone was added to continue the reaction, thereby obtaining the methyl radical compound.

[0046] The present invention involves mixing the compound M1, the amine derivatives corresponding to R1, R2 or R3, tris(dibenzylacetone)palladium, sodium tert-butoxide, tritert-butylphosphine tetrafluoroborate and toluene and carrying out a metal-catalyzed coupling reaction to obtain the intermediate product.

[0047] In this invention, the molar ratio of compound M1 to the amine derivatives corresponding to R1, R2 or R3 is preferably 1:(1~2), more preferably 1:1.5.

[0048] In this invention, the molar ratio of compound M1 to tris(dibenzylacetone)palladium is preferably 1:(0.05~0.1), more preferably 1:0.1.

[0049] In this invention, the molar ratio of compound M1 to sodium tert-butoxide is preferably 1:(2~5), more preferably 1:4. In this invention, the molar ratio of compound M1 to tritert-butylphosphine tetrafluoroborate is preferably 1:(0.05~0.1), more preferably 1:0.1.

[0050] The present invention does not impose any special limitation on the amount of toluene used; any amount known to those skilled in the art can be used.

[0051] In this invention, the metal-catalyzed coupling reaction is preferably carried out in a protective atmosphere, preferably an argon atmosphere, and the temperature of the metal-catalyzed coupling reaction is preferably 90~120℃, and the time is preferably 10~30h.

[0052] After the metal-catalyzed coupling reaction is completed, the present invention preferably includes sequential filtration, vacuum distillation, column chromatography separation and drying; the present invention does not have any special limitations on the filtration, vacuum distillation, column chromatography separation and drying, and any process known to those skilled in the art can be used.

[0053] After obtaining the intermediate product, the present invention mixes the intermediate product with a mixed solvent of acetonitrile and tetrahydrofuran, adds a tetrabutylammonium hydroxide methanol solution, stirs overnight, adds tetrachlorobenzoquinone, and continues the reaction to obtain the methyl radical compound. The above process preferably refers to the corresponding process described in the above technical solution, and will not be repeated here.

[0054] The present invention also provides the application of the methyl radical compound described in the above technical solution in organic electroluminescent devices.

[0055] In this invention, the organic electroluminescent device includes a substrate, an anode, a hole transport layer, an organic light-emitting layer, an electron transport layer, and a cathode layer stacked sequentially.

[0056] In this invention, the substrate is preferably a transparent substrate well known to those skilled in the art. In an embodiment of this invention, the substrate is ITO.

[0057] In this invention, the anode is preferably an inorganic material or an organic conductive polymer; the inorganic material is preferably a metal oxide or a metal; the metal oxide is preferably one or more of ITO, zinc oxide and zinc tin oxide; the metal is preferably one or more of gold, copper and silver; and the organic conductive polymer is preferably polythiophene / sodium polyvinylbenzenesulfonate (PEDOT:PSS) or polyaniline (PANI).

[0058] In this invention, the hole transport layer is preferably an aromatic amine derivative, more preferably N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB) or TAPC.

[0059] In this invention, the material of the organic light-emitting layer preferably includes a parent material and the methyl radical compound described in the above technical solution; the mass concentration of the methyl radical compound and the parent material is preferably 0.1% to 50%, more preferably 0.3% to 30%. In this invention, the parent material is preferably 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN).

[0060] In this invention, the material of the electron transport layer is preferably POT2T or 1,3,5-tris(1-phenyl-1-hydro-benzimidazol-2-yl)benzene (TPBi).

[0061] In this invention, the cathode layer preferably consists of a LiF layer and an Al layer stacked sequentially.

[0062] In this invention, the organic electroluminescent device preferably includes a hole injection layer, which is preferably located between the anode and the hole transport layer; the material of the hole injection layer is preferably a metal oxide, which is preferably molybdenum trioxide or an aromatic amine derivative; the aromatic amine derivative is preferably m-MTDATA.

[0063] In this invention, the organic electroluminescent device preferably includes an electron injection layer, which is preferably located between the electron transport layer and the cathode layer, and the material of the electron injection layer is preferably lithium fluoride, cesium fluoride, or cesium carbonate.

[0064] In this invention, the organic electroluminescent device preferably further includes a hole-blocking layer, which is preferably located between the electron transport layer and the light-emitting layer. The hole-blocking layer is preferably 2,9-dimethyl-4,7-biphenyl-1,10-o-phenanthroline (BCP).

[0065] In this invention, the organic electroluminescent device preferably further includes an electron blocking layer, which is preferably located between the hole transport layer and the organic light-emitting layer. The material of the electron blocking layer is preferably 4,4',4''-tris(carbazole-9-yl)triphenylamine (TCTA), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline (TAPC), or 1,3'-bis(9-carbazole)benzene (CBP).

[0066] The technical solutions of this invention will be clearly and completely described below with reference to the embodiments thereof. Obviously, the described embodiments are only a part of the embodiments of this invention, and not all of them. All other embodiments obtained by those skilled in the art based on the embodiments of this invention without creative effort are within the scope of protection of this invention.

[0067] Synthesis of intermediate M1: The synthesis route is shown in equation a: Formula a; The specific preparation process is as follows: In a 350 mL pressure flask, 2,4,6-trichloro-5-pyrimidinecarboxaldehyde (5.00 g, 23.65 mmol, 1.00 equivalent), 1,3,5-trichlorobenzene (10.73 g, 59.12 mmol, 2.50 equivalent), and trifluoromethanesulfonic acid (70.98 g, 472.98 mmol, 20.00 equivalent) were added sequentially. The flask was then sealed and heated at 180 °C for 24 h. After cooling to room temperature, the reaction mixture was neutralized to pH 7 with an aqueous sodium bicarbonate solution, followed by multiple extractions with dichloromethane. The combined organic phases were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using petroleum ether as eluent to give a white solid M1 in 48.19% (6.43 g). MALDI-TOF (m / z): [m]+ Theoretical value: C 17 H5C l9 N2 = 556, measured value: 556.

[0068] Synthesis of intermediate M8: The preparation of compound M8 was as follows: 2,4,6-tribromo-5-pyrimidinecarboxaldehyde (8.10 g, 23.51 mmol, 1.00 equivalent), 1,3,5-tribromobenzene (18.50 g, 58.77 mmol, 2.50 equivalent), and trifluoromethanesulfonic acid (71.98 g, 47498 mmol, 20.00 equivalent) were added sequentially to a 350 mL pressure flask. The flask was then sealed and heated at 180°C for 24 h. After cooling to room temperature, the reaction mixture was neutralized to pH 7 with an aqueous sodium bicarbonate solution, followed by multiple extractions with dichloromethane. The combined organic phases were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using petroleum ether as eluent to give white solid M8 in a yield of 54.71% (12.30 g). MALDI-TOF (m / z): [m]+ Theoretical value: C 17 H5Br9N2 = 956, measured value: 956.

[0069] Example 1 The synthetic routes for compounds 1-2 are shown below: Under an argon atmosphere, 9,9-dimethyl-10-(naphth-2-yl)-9,10-dihydroacrylamide boronic acid ester (2.70 g, 5.85 mmol, 1.00 equivalent), M1 (3.91 g, 7.02 mmol, 1.20 equivalent), K2CO3 (3.23 g, 23.41 mmol, 4.00 equivalent), and Pd(PPh3)4 (0.34 g, 0.29 mmol, 0.05 equivalent) were dissolved in a mixed solvent of toluene (48 mL), ethanol (6 mL), and ultrapure water (12 mL). The reaction mixture was stirred at 90 °C for 24 h. After cooling to room temperature, the mixture was poured into a saturated aqueous NaCl solution and extracted three times with dichloromethane (50 mL × 3). After drying, reduced pressure concentration, and purification by silica gel column chromatography (petroleum ether / dichloromethane = 3:1, v / v), a pale yellow powder M2 was obtained, with a yield of 80.92% (4.05 g). MALDI-TOF (m / z): [m]+ Theoretical value: C 42 H 25 Cl8N3 = 855, measured value: 854.

[0070] M2 (2.30 g, 2.69 mmol, 1.00 equivalent) was dissolved in a mixed solvent of acetonitrile (60 mL) and tetrahydrofuran (20 mL) under an argon atmosphere. Then, 1.5 M tetrabutylammonium hydroxide methanol solution (2.09 g, 8.07 mmol, 3.00 equivalent) was added, and the mixture was stirred overnight in the dark. Tetrachlorobenzoquinone (1.65 g, 6.72 mmol, 2.50 equivalent) was then added, and the reaction mixture was stirred again for 4 h at room temperature. The resulting solution was filtered through diatomaceous earth and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (petroleum ether / dichloromethane = 3:1, v / v), dried under vacuum, to give reddish-brown solid 1-2, yield 70.95% (1.63 g). MALDI-TOF (m / z): [m]+ Theoretical value: C 42 H 25 Cl8N3=854, measured value: 854.

[0071] Example 2 The synthetic routes for compounds 1-9 are shown below: Triphenylamine borate (2.30 g, 6.19 mmol, 1.00 equivalent), M1 (4.14 g, 7.43 mmol, 1.20 equivalent), K2CO3 (3.42 g, 24.78 mmol, 4.00 equivalent), and Pd(PPh3)4 (0.36 g, 0.31 mmol, 0.05 equivalent) were dissolved in a mixed solvent of toluene (48 mL), ethanol (6 mL), and ultrapure water (12 mL) under an argon atmosphere. The reaction mixture was stirred at 90 °C for 24 h. After cooling to room temperature, the mixture was poured into a saturated aqueous NaCl solution and extracted three times with dichloromethane (50 mL × 3). The combined organic layers were dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (petroleum ether / dichloromethane = 3:1, v / v) to give a pale yellow solid M3 in 79.12% (3.75 g). MALDI-TOF (m / z): [m] + theoretical value: C 42 H 25 Cl8N3 = 765.16, measured value: 765.24.

[0072] M3 (2.00 g, 2.61 mmol, 1.00 equivalent) was dissolved in a mixture of acetonitrile (60 mL) and tetrahydrofuran (20 mL) under an argon atmosphere. Then, 1.5 M tetrabutylammonium hydroxide methanol solution (2.03 g, 7.84 mmol, 3.00 equivalent) was added, and the mixture was stirred overnight in the dark. Tetrachlorobenzoquinone (1.61 g, 6.53 mmol, 2.50 equivalent) was then added, and the reaction mixture was stirred at room temperature for 4 h. The resulting solution was filtered through diatomaceous earth, concentrated under reduced pressure, and purified by silica gel column chromatography (petroleum ether / dichloromethane = 3:1, v / v). The product was dried under vacuum to give reddish-brown solid 1-9 in a yield of 74.10% (1.48 g). MALDI-TOF (m / z): [m]+ Theoretical value: C 42 H 25 Cl8N3 = 764, measured value: 764.

[0073] Example 3 The synthetic routes for compounds 1-10 are shown below: Under an argon atmosphere, 10-phenyl-2-(4,4,5-tetramethyl-1,3,2-dioxaborphane-2-yl)-10H-spiro[acridin-9,9'-oxazanthene] (3.00 g, 5.46 mmol, 1.00 equivalent), M1 (3.64 g, 6.55 mmol, 1.20 equivalent), K2CO3 (3.02 g, 21.84 mmol, 4.00 equivalent), and Pd(PPh3)4 (0.32 g, 0.27 mmol, 0.05 equivalent) were dissolved in a mixed solvent of toluene (48 mL), ethanol (6 mL), and ultrapure water (12 mL). The reaction mixture was stirred at 90 °C for 24 h. After cooling to room temperature, the mixture was poured into a saturated aqueous NaCl solution and extracted three times with dichloromethane (50 mL × 3). The combined organic layers were dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (petroleum ether / dichloromethane = 3:1, v / v) to give a pale yellow solid M4 in 81.55% (4.20 g). MALDI-TOF (m / z): [m]+ Theoretical value: C 48 H 25 Cl8N3O = 943, measured value: 943.

[0074] M4 (3.00 g, 3.18 mmol, 1.00 equivalent) was dissolved in a mixture of acetonitrile (60 mL) and tetrahydrofuran (20 mL) under an argon atmosphere. Then, 1.5 M tetrabutylammonium hydroxide methanol solution (2.48 g, 9.54 mmol, 3.00 equivalent) was added, and the mixture was stirred overnight in the dark. Tetrachlorobenzoquinone (1.95 g, 7.95 mmol, 2.50 equivalent) was then added, and the reaction mixture was stirred at room temperature for 4 h. The resulting solution was filtered through diatomaceous earth, concentrated under reduced pressure, and purified by silica gel column chromatography (petroleum ether / dichloromethane = 3:1, v / v). The product was dried under vacuum to give 1-10 reddish-brown solids in a yield of 77.33% (2.32 g). MALDI-TOF (m / z): [m]+ Theoretical value: C 48 H 25 Cl8N3O = 942, measured value: 942.

[0075] Example 4 The synthetic routes for compounds 1-11 are shown below: Under an argon atmosphere, 10-phenyl-2-(4,4,5-tetramethyl-1,3,2-dioxaborhexacyclopentan-2-yl)-10H-spiro[acridin-9,9'-fluorene] (3.00 g, 5.62 mmol, 1.00 equivalent), M1 (3.75 g, 6.75 mmol, 1.20 equivalent), K2CO3 (3.11 g, 22.49 mmol, 4.00 equivalent), and Pd(PPh3)4 (0.32 g, 0.28 mmol, 0.05 equivalent) were dissolved in a mixed solvent of toluene (48 mL), ethanol (6 mL), and ultrapure water (12 mL). The reaction mixture was stirred at 90 °C for 24 h. After cooling to room temperature, the mixture was poured into a saturated aqueous NaCl solution and extracted three times with dichloromethane (50 mL × 3). The combined organic layers were dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (petroleum ether / dichloromethane = 3:1, v / v) to give a pale yellow solid M5 in 81.55% (4.20 g). MALDI-TOF (m / z): [m]+ Theoretical value: C 48 H 25 Cl8N3 = 927, measured value: 927.

[0076] M5 (3.00 g, 3.24 mmol, 1.00 equivalent) was dissolved in a mixture of acetonitrile (60 mL) and tetrahydrofuran (20 mL) under an argon atmosphere. Then, 1.5 M tetrabutylammonium hydroxide methanol solution (2.52 g, 9.71 mmol, 3.00 equivalent) was added, and the mixture was stirred overnight in the dark. Tetrachlorobenzoquinone (1.99 g, 8.09 mmol, 2.50 equivalent) was then added, and the reaction mixture was stirred at room temperature for 4 h. The resulting solution was filtered through diatomaceous earth, concentrated under reduced pressure, and purified by silica gel column chromatography (petroleum ether / dichloromethane = 3:1, v / v). The product was dried under vacuum to give a reddish-brown solid 1-11 in a yield of 84.43% (2.53 g). MALDI-TOF (m / z): [m]+ Theoretical value: C 48 H 25 Cl8N3 = 926, measured value: 926.

[0077] Example 5 The structural formulas and synthetic routes of compounds 1-12 are shown in the figure below: Under an argon atmosphere, 4,4,-di-tert-butyl-4-boronic acid pinacol ester triphenylamine (3.00 g, 5.32 mmol, 1.00 equivalent), M1 (3.45 g, 6.25 mmol, 1.20 equivalent), K2CO3 (3.01 g, 22.09 mmol, 4.00 equivalent), and Pd(PPh3)4 (0.31 g, 0.28 mmol, 0.05 equivalent) were dissolved in a mixed solvent of toluene (48 mL), ethanol (6 mL), and ultrapure water (12 mL). The reaction mixture was stirred at 90 °C for 24 h. After cooling to room temperature, the mixture was poured into a saturated aqueous NaCl solution and extracted three times with dichloromethane (50 mL × 3). The combined organic layers were dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (petroleum ether / dichloromethane = 3:1, v / v) to give a pale yellow solid M6 in 83.45% (4.40 g). MALDI-TOF (m / z): [m]+ Theoretical value: C 48 H 25 Cl8N3 = 877, measured value: 877.

[0078] M6 (3.00 g, 3.04 mmol, 1.00 equivalent) was dissolved in a mixture of acetonitrile (60 mL) and tetrahydrofuran (20 mL) under an argon atmosphere. Then, 1.5 M tetrabutylammonium hydroxide methanol solution (2.02 g, 9.01 mmol, 3.00 equivalent) was added, and the mixture was stirred overnight in the dark. Tetrachlorobenzoquinone (1.89 g, 7.89 mmol, 2.50 equivalent) was then added, and the reaction mixture was stirred at room temperature for 4 h. The resulting solution was filtered through diatomaceous earth, concentrated under reduced pressure, and purified by silica gel column chromatography (petroleum ether / dichloromethane = 3:1, v / v). The product was dried under vacuum to give reddish-brown solid 1-12 in 81.00% (2.43 g). MALDI-TOF (m / z): [m]+ Theoretical value: C 48 H 25 Cl8N3 = 925, measured value: 925.

[0079] Example 6 The structural formulas and synthetic routes of compounds 1-16 are shown in the figure below: Under an argon atmosphere, 2,4,6-trimethylboronic acid ester (6.00 g, 24.37 mmol, 3.20 equivalents), M1 (4.24 g, 7.62 mmol, 1.00 equivalents), K2CO3 (6.32 g, 45.70 mmol, 6.00 equivalents), and Pd(PPh3)4 (0.44 g, 0.38 mmol, 0.05 equivalents) were dissolved in a mixed solvent of toluene (96 mL), ethanol (12 mL), and ultrapure water (24 mL). The reaction mixture was stirred at 90 °C for 24 h. After cooling to room temperature, the mixture was poured into a saturated aqueous NaCl solution and extracted three times with dichloromethane (100 mL × 3). The combined organic layers were dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (petroleum ether / dichloromethane = 3:1, v / v) to give a pale yellow solid M7 in 83.45% (4.40 g). MALDI-TOF (m / z): [m]+ Theoretical value: C 44 H 37 Cl6N2 = 807, measured value: 807.

[0080] M7 (3.00 g, 3.72 mmol, 1.00 equivalent) was dissolved in a mixture of acetonitrile (60 mL) and tetrahydrofuran (20 mL) under an argon atmosphere. Then, 1.5 M tetrabutylammonium hydroxide methanol solution (2.89 g, 11.15 mmol, 3.00 equivalent) was added, and the mixture was stirred overnight in the dark. Tetrachlorobenzoquinone (2.28 g, 9.28 mmol, 2.50 equivalent) was then added, and the reaction mixture was stirred at room temperature for 4 h. The resulting solution was filtered through diatomaceous earth, concentrated under reduced pressure, and purified by silica gel column chromatography (petroleum ether / dichloromethane = 3:1, v / v). The product was dried under vacuum to give a reddish-brown solid 1-12 in 84.44% (2.53 g). MALDI-TOF (m / z): [m]+ Theoretical value: C 48 H 24 Cl8N3 = 924, measured value: 924.

[0081] Example 7 The structural formulas and synthetic routes of compounds 1-19 are shown in the figure below: Under an argon atmosphere, M8 (4.00 g, 4.18 mmol, 1.00 equivalent), phenoxazine (1.15 g, 6.27 mmol, 1.50 equivalent), Cs₂CO₃ (4.08 g, 12.54 mmol, 3.00 equivalent), tri-tert-butylphosphine tetrafluoroborate (0.12 g, 0.40 mmol, 0.10 equivalent), and Pd(OAc)₂ (0.09 g, 0.40 mmol, 0.10 equivalent) were dissolved in toluene (100 mL). The reaction mixture was stirred at 110 °C for 24 h. After cooling to room temperature, the mixture was poured into a saturated aqueous NaCl solution and extracted three times with dichloromethane (50 mL × 3). The combined organic layers were dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (petroleum ether / dichloromethane = 3:1, v / v) to give a pale yellow solid M9 in 86.27% (3.82 g). MALDI-TOF (m / z): [m]+ Theoretical value: C 29 H 13 C l8 N3O = 1058, measured value: 1058.

[0082] M9 (3.82 g, 3.61 mmol, 1.00 equivalent) was dissolved in a mixture of acetonitrile (60 mL) and tetrahydrofuran (20 mL) under an argon atmosphere. Then, 1.5 M tetrabutylammonium hydroxide methanol solution (3.25 g, 12.54 mmol, 3.00 equivalent) was added, and the mixture was stirred overnight in the dark. Tetrachlorobenzoquinone (3.08 g, 12.54 mmol, 3.00 equivalent) was then added, and the reaction mixture was stirred at room temperature for 4 h. The resulting solution was filtered through diatomaceous earth, concentrated under reduced pressure, and purified by silica gel column chromatography (petroleum ether / dichloromethane = 3:1, v / v). The product was dried under vacuum to give a reddish-brown solid 1-19 in a yield of 80.62% (3.08 g). MALDI-TOF (m / z): [m]+ Theoretical value: C 48 H 24 C l8 N3 = 1057, measured value: 1057.

[0083] Example 8 The structural formulas and synthetic routes of compounds 1-24 are shown in the figure below: Under an argon atmosphere, 9,9-dimethyl-10-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentan-2-yl)phenyl)-9,10-dihydroacridine (1.79 g, 4.36 mmol, 1.00 equivalent), M8 (5.00 g, 5.22 mmol, 1.20 equivalent), K2CO3 (2.41 g, 17.41 mmol, 4.00 equivalent), and Pd(PPh3)4 (0.25 g, 0.21 mmol, 0.05 equivalent) were dissolved in a mixed solvent of toluene (48 mL), ethanol (6 mL), and ultrapure water (12 mL). The reaction mixture was stirred at 90 °C for 24 h. After cooling to room temperature, the mixture was poured into a saturated aqueous NaCl solution and extracted three times with dichloromethane (50 mL × 3). The combined organic layers were dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (petroleum ether / dichloromethane = 3:1, v / v) to give a pale yellow solid M10 in 83.14% (4.20 g). MALDI-TOF (m / z): [m]+ Theoretical value: C 38 H 23 Cl8N3 = 1160, measured value: 1160.

[0084] M9 (4.20 g, 3.62 mmol, 1.00 equivalent) was dissolved in a mixture of acetonitrile (60 mL) and tetrahydrofuran (20 mL) under an argon atmosphere. Then, 1.5 M tetrabutylammonium hydroxide methanol solution (2.82 g, 10.86 mmol, 3.00 equivalent) was added, and the mixture was stirred overnight in the dark. Tetrachlorobenzoquinone (2.67 g, 10.86 mmol, 3.00 equivalent) was then added, and the reaction mixture was stirred for 4 h at room temperature. The resulting solution was filtered through diatomaceous earth, concentrated under reduced pressure, and purified by silica gel column chromatography (petroleum ether / dichloromethane = 3:1, v / v). The product was dried under vacuum to give a reddish-brown solid 1-24, in a yield of 87.14% (3.66 g). MALDI-TOF (m / z): [m]+ Theoretical value: C 38 H 22 Cl8N3 = 1159, measured value: 1159.

[0085] Example 9 The preparation process is the same as in Example 1, except that 9,9-dimethyl-10-(naphth-2-yl)-9,10-dihydroacrylborate is replaced with Compound 1-31 was prepared. The yield was 65%, and the mass spectrometry value was 913.

[0086] Example 10 The preparation process is the same as in Example 1, except that M1 is replaced with Replace 9,9-dimethyl-10-(naphth-2-yl)-9,10-dihydroacrylamide with Compound 1-35 was prepared. The yield was 63%, and the mass spectrometry value was 1463.

[0087] Example 11 The preparation process is the same as in Example 1, except that M1 is replaced with Replace 9,9-dimethyl-10-(naphth-2-yl)-9,10-dihydroacrylamide with Compound 1-36 was prepared. The yield was 61%, and the mass spectrometry value was 2027.

[0088] Example 12 The preparation process is the same as in Example 1, except that M1 is replaced with Replace 9,9-dimethyl-10-(naphth-2-yl)-9,10-dihydroacrylamide with Compound 1-38 was prepared. The yield was 65%, and the mass spectrometry value was 1220.

[0089] Example 13 The preparation process is the same as in Example 1, except that M1 is replaced with Replace 9,9-dimethyl-10-(naphth-2-yl)-9,10-dihydroacrylamide with Compound 1-39 was prepared. The yield was 60%, and the mass spectrometry value was 695.

[0090] Example 14 The preparation process is the same as in Example 1, except that M1 is replaced with Replace 9,9-dimethyl-10-(naphth-2-yl)-9,10-dihydroacrylamide with Compound 1-37 was prepared. The yield was 62%, and the mass spectrometry value was 1042.

[0091] Example 15 The preparation process is the same as in Example 1, except that M1 is replaced with Replace 9,9-dimethyl-10-(naphth-2-yl)-9,10-dihydroacrylamide with Compound 1-40 was prepared. The yield was 66%, and the mass spectrometry value was 1710.

[0092] Example 16 The preparation process is the same as in Example 1, except that M1 is replaced with Compounds 1-3 were prepared. The yield was 65%, and the mass spectrometry value was 1209.

[0093] Example 17 The preparation process is the same as in Example 1, except that 9,9-dimethyl-10-(naphth-2-yl)-9,10-dihydroacrylamide boronic acid ester is replaced with Compounds 1-6 were prepared. The yield was 68%, and the mass spectrometry value was 954.

[0094] Example 18 The preparation process is the same as in Example 7, except that phenoxazine is replaced with Compound 1-18 was prepared. The yield was 68%, and the mass spectrometry value was 688.

[0095] Example 19 The preparation process is the same as in Example 7, except that M1 is replaced with [missing information] and phenoxazine is replaced with [missing information]. Compound 1-21 was prepared. The yield was 63%, and the mass spectrometry value was 596.

[0096] Example 20 The preparation process is the same as in Example 1, except that 9,9-dimethyl-10-(naphth-2-yl)-9,10-dihydroacrylamide boronic acid ester is replaced with Compound 1-23 was prepared. The yield was 69%, and the mass spectrometry value was 762.

[0097] Example 21 The preparation process is the same as in Example 1, except that M1 is replaced with Replace 9,9-dimethyl-10-(naphth-2-yl)-9,10-dihydroacrylamide with Compound 1-28 was prepared. The yield was 62%, and the mass spectrometry value was 1107.

[0098] Example 22 The preparation process is the same as in Example 1, except that M1 is replaced with Replace 9,9-dimethyl-10-(naphth-2-yl)-9,10-dihydroacrylamide with Compound 1-30 was prepared. The yield was 64%, and the mass spectrometry value was 1149.

[0099] Example 23 The preparation process is the same as in Example 1, except that M1 is replaced with Replace 9,9-dimethyl-10-(naphth-2-yl)-9,10-dihydroacrylamide with Compound 1-34 was prepared. The yield was 64%, and the mass spectrometry value was 913.

[0100] Test case Figure 1 The ultraviolet absorption spectra (UV-Vis) and room temperature fluorescence spectra (PL) of compounds 1-2 and 1-9 are obtained in dilute solutions of cyclohexane (1×10⁻⁶). -5 Measured in mol / L, from Figure 1 It can be seen that both molecules possess near-infrared luminescence properties; Figure 2 The EPR plots for compounds 1-2 and 1-9 are provided by [the relevant authority / organism]. Figure 2 It can be seen that two free radical molecules were successfully prepared.

[0101] Application Example 1 The structure of the organic electroluminescent device is as follows: ITO / MoO3 (3 nm) / TAPC (40 nm, hole transport layer) / compound 1-2: 2-methyl-9,10-di(naphthyl-2-yl)anthracene (MADN) (5 wt. %, 25 nm, light-emitting layer) / POT2T (70 nm, electron transport layer) / LiF (0.8 nm) / Al (100 nm); The fabrication method of the organic electroluminescent device is as follows: ITO glass is used as the substrate, and the substrate treatment process is as follows: it is cleaned with toluene, acetone, ethanol, and deionized water, followed by ultrasonic cleaning, and then treated with ultraviolet light. The evaporation material is placed in different quartz crucibles of a multi-source organic molecular vapor deposition system, and organic materials of different compositions and thicknesses are grown according to the designed structure. During the growth process, the vacuum degree of the system is maintained at 3 × 10⁻⁶. -4 Approximately Pa. The thickness and growth rate of the grown material are monitored by a film thickness controller; Figure 3 The electroluminescence spectrum of the organic electroluminescent device at 13V is given by... Figure 3 It can be seen that the peak wavelength of the organic electroluminescent device at a voltage of 13V is located at 855nm, which is near-infrared light, indicating that compounds 1-2 can achieve electroluminescence. Figure 4 The graph shows the external quantum efficiency-voltage characteristic of the organic electroluminescent device. Figure 4 It is known that the maximum external quantum efficiency of the organic electroluminescent device is 7.7%; Figure 5 The voltage-current density and voltage-radiance characteristic curves of the organic electroluminescent device are given by... Figure 5 It can be seen that the maximum radiance of the organic electroluminescent device is 30147 mW·sr. -1 ·m -2 .

[0102] Application Example 2 Organic electroluminescent device reference application example 1, the difference being that compound 1-2 is replaced with compound 1-3; The organic electroluminescent device exhibits a peak wavelength of 858 nm at 14 V, which is near-infrared light. The maximum external quantum efficiency of the organic electroluminescent device is 5.7%, and the maximum radiance is 21567 mW·sr. -1 ·m -2 .

[0103] Application Example 3 Organic electroluminescent devices are referenced in Example 1, except that compounds 1-2 are replaced with compounds 1-6. The organic electroluminescent device exhibits a peak wavelength of 821 nm at 14 V, which is near-infrared light. The maximum external quantum efficiency of the organic electroluminescent device is 3.1%, and the maximum radiance is 23567 mW·sr. -1 ·m -2 .

[0104] Application Example 4 Organic electroluminescent device reference application example 1, the difference being that compound 1-2 is replaced with compound 1-18; The organic electroluminescent device exhibits a peak wavelength of 811 nm at 14 V, which is near-infrared light. The maximum external quantum efficiency of the organic electroluminescent device is 2.9%, and the maximum radiance is 56741 mW·sr. -1 ·m -2 .

[0105] Application Example 5 Organic electroluminescent device reference application example 1, the difference being that compound 1-2 is replaced with compound 1-20; The organic electroluminescent device exhibits a peak wavelength of 815 nm at 14 V, which is near-infrared light. The maximum external quantum efficiency of the organic electroluminescent device is 3.5%, and the maximum radiance is 53248 mW·sr. -1 ·m -2 .

[0106] Application Example 6 Organic electroluminescent device reference application example 1, the difference being that compound 1-2 is replaced with compound 1-21; The organic electroluminescent device exhibits a peak wavelength of 828 nm at 14 V, which is near-infrared light. The maximum external quantum efficiency of the organic electroluminescent device is 3.7%, and the maximum radiance is 24785 mW·sr. -1 ·m -2 .

[0107] Application Example 7 Organic electroluminescent device reference application example 1, the difference being that compound 1-2 is replaced with compound 1-23; The organic electroluminescent device exhibits a peak wavelength of 835 nm at 14 V, which is near-infrared light. The maximum external quantum efficiency of the organic electroluminescent device is 3.2%, and the maximum radiance is 65434 mW·sr. -1 ·m -2 .

[0108] Application Example 8 Organic electroluminescent device reference application example 1, the difference being that compound 1-2 is replaced with compound 1-24; The organic electroluminescent device exhibits a peak wavelength of 854 nm at 14 V, which is near-infrared light. The maximum external quantum efficiency of the organic electroluminescent device is 3.2%, and the maximum radiance is 20364 mW·sr. -1 ·m -2 .

[0109] Application Example 9 Organic electroluminescent device reference application example 1, the difference being that compound 1-2 is replaced with compound 1-28; The organic electroluminescent device exhibits a peak wavelength of 848 nm at 14 V, which is near-infrared light. The maximum external quantum efficiency of the organic electroluminescent device is 4.2%, and the maximum radiance is 2364 mW·sr. -1 ·m -2 .

[0110] Application Example 10 Organic electroluminescent device reference application example 1, the difference being that compound 1-2 is replaced with compound 1-30; The organic electroluminescent device exhibits a peak wavelength of 856 nm at 14 V, which is near-infrared light. The maximum external quantum efficiency of the organic electroluminescent device is 2.3%, and the maximum radiance is 8541 mW·sr. -1 ·m -2 .

[0111] Application Example 11 Organic electroluminescent device reference application example 1, the difference being that compound 1-2 is replaced with compound 1-34; The organic electroluminescent device exhibits a peak wavelength of 896 nm at 14 V, which is near-infrared light. The maximum external quantum efficiency of the organic electroluminescent device is 1.3%, and the maximum radiance is 1041 mW·sr. -1 ·m -2 .

[0112] The above description is merely a preferred embodiment of the present invention and is not intended to limit the present invention in any way. It should be noted that those skilled in the art can make various improvements and modifications without departing from the principles of the present invention, and these improvements and modifications should also be considered within the scope of protection of the present invention.

Claims

1. A methyl radical compound, characterized in that, having the structure of Formula 1: Formula 1; In the formula 1, X1, X1 1 , X2, X2 1 , X2 2 , X2 3 , X3, X3 1 , X3 2 and X3 3 are independently a hydrogen atom, a deuterium atom, a halogen, a cyano group, an unsubstituted alkyl group, an R 1 substituted alkyl group, an unsubstituted alkoxy group, an R 1 substituted alkoxy group, an unsubstituted alkenyl group, an R 1 substituted alkenyl group, an unsubstituted alkynyl group, an R 1 substituted alkynyl group, an unsubstituted aryl group, an R 1 substituted aryl group, an unsubstituted heteroaryl group, or an R 1 substituted heteroaryl group; R1, R2and R3are independently hydrogen atom, deuterium atom, halogen, cyano, -NO2, -N(R 1 )2, -OR 1 , -SR 1 , -C(=O)R 1 , -P(=O)R 1 , -Si(R 1 )3, unsubstituted alkoxy, R 1 substituted alkoxy, unsubstituted alkyl, R 1 substituted alkyl, unsubstituted alkenyl, R 1 substituted alkenyl, unsubstituted alkynyl, R 1 substituted alkynyl, unsubstituted aryl, R 1 substituted aryl, unsubstituted heteroaryl or R 1 substituted heteroaryl; The X1, X1 1 X2, X2 1 X2 2 X2 3 X3, X3 1 X3 2 and X3 3 Chinese R 1 Substituted alkyl, R 1 Substituted alkoxy groups, R 1 Substituted alkenyl, R 1 Substituted alkynyl group, R 1 Substituted aryl and R 1 Substituted heteroaryl groups, the N(R) 1 )2、-OR 1 -SR 1 -C(=O)R 1 -P(=O)R 1 and -Si(R 1 )3 in R 1 And R in R1, R2 and R3 1 Substituted alkoxy groups, R 1 Substituted cycloalkyl, R 1 Substituted alkenyl, R 1 Substituted alkynyl group, R 1 Substituted aryl and R 1 The substituted heteroaryl groups are all independently hydrogen atoms, deuterium atoms, halogens, cyano groups, -NO2, -N(R) 2 )2、-OR 2 -SR 2 -C(=O)R 2 -P(=O)R 2 、-Si(R 2 3. R 2 Substituted alkyl, R 2 Substituted alkenyl, R 2 Substituted alkynyl group, R 2 Substituted aromatic hydrocarbon groups or R 2 Substituted aromatic heterocyclic groups; The -NO2, -N(R) 2 )2、-OR 2 -SR 2 -C(=O)R 2 -P(=O)R 2 and -Si(R 2 )3 in R 2 and the R 2 Substituted alkenyl, R 2 Substituted alkynyl group, R 2 Substituted aromatic hydrocarbon groups and R 2 R in substituted aromatic heterocyclic groups 2 Each of these can be independently composed of a hydrogen atom, a deuterium atom, a halogen, a cyano group, an alkyl group, an alkoxy group, a cycloalkyl group, an alkenyl group, an aryl group, or a heteroaryl group.

2. The methyl radical compound according to claim 1, wherein X1, X1 1 X2, X2 1 X2 2 X2 3 X3, X3 1 X3 2 or X3 3 among which, the unsubstituted alkyl or R 1 the number of carbon atoms in the alkyl moiety of the substituted alkyl is independently 1 to 20; the unsubstituted alkoxy or R 1 the number of carbon atoms in the alkoxy moiety of the substituted alkoxy group is independently 1 to 20; the unsubstituted alkenyl group or R 1 the number of carbon atoms in the alkenyl group of the substituted alkenyl group is independently 2 to 20; the unsubstituted alkynyl group or R 1 the number of carbon atoms in the alkynyl group in the substituted alkynyl group is independently 2 to 20; the unsubstituted aryl group or R 1 the number of carbon atoms in the aryl group of the substituted aryl group is independently 6 to 40; the unsubstituted heteroaryl or R 1 the number of carbon atoms in the substituted heteroaryl group is independently 6 to 40; R 1 substituted alkyl, R 1 substituted alkoxy, R 1 substituted alkenyl, R 1 substituted alkynyl, R 1 substituted aryl, and R 1 substituted heteroaryl, R 1 is ≥ 1.

3. The methyl radical compound according to claim 2, wherein the unsubstituted alkyl group includes a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a neopentyl group, an n-hexyl group, an n-heptyl group, a 2-methylhexyl group, an n-octyl group, an iso-octyl group, a tert-octyl group, a 2-ethylhexyl group, a 3-methylheptyl group, an n-nonyl group, an n-decyl group, a hexadecyl group, an octadecyl group, an eicosyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, or a cyclooctyl group; the unsubstituted alkoxy group is the unsubstituted alkyl group substituted with ≥1 alkoxy group; the unsubstituted alkenyl group includes an ethenyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group, a decenyl group, an undecenyl group, a dodecenyl group, a tridecenyl group, a tetradecenyl group, a pentadecenyl group, a hexadecenyl group, a heptadecenyl group, an octadecenyl group, a nonadecenyl group, an icosapentenyl group, a 2-ethylhexenyl group, an allyl group, or a cyclohexenyl group; the unsubstituted alkynyl group includes an ethynyl group, an iso-propynyl group, a butynyl group, a pentynyl group, a hexynyl group, a heptynyl group, an octynyl group, a nonynyl group, or a decynyl group; the unsubstituted aryl group includes a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, or a quinquephenyl group; the unsubstituted heteroaryl group includes a benzo-thienocarbazolyl group, a benzo-furanocarbazolyl group, a benzo-fluorencarbazolyl group, a benzoanthracenyl group, a benzophenanthryl group, a fluorenyl group, a spirobifluorenyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, an N-phenylcarbazolyl group, an indenocarbazolyl group, a benzoimidazolyl group, a diphenyl-benzoimidazolyl group, a diphenyl-oxadiazolyl group, a diphenyl-boryl group, a triphenyl-phosphoroxyl group, a diphenyl-phosphoroxyl group, a triphenyl-siliconyl group, or a tetraphenyl-siliconyl group.

4. The methyl radical compound according to claim 1, wherein in the R1, R2, and R3, the unsubstituted alkoxy and R 1 the number of carbon atoms in the alkoxy moiety of the substituted alkoxy group is independently 1 to 20; the unsubstituted alkyl and R 1 the number of carbon atoms in the cycloalkyl portion of the substituted alkyl is independently 3 to 10; the unsubstituted alkenyl and R 1 the number of carbon atoms in the alkenyl portion of the substituted alkenyl is independently 2 to 20; the unsubstituted alkynyl group and R 1 the number of carbon atoms in the alkynyl moiety of the substituted alkynyl group is independently 2 to 20; the unsubstituted aryl group and R 1 the number of carbon atoms in the aryl moiety of the substituted aryl group is independently 6 to 40; the unsubstituted heteroaryl or R 1 the number of carbon atoms in the heteroaryl moiety of the substituted heteroaryl is independently 5 to 40; R 1 substituted alkoxy, R 1 substituted cycloalkyl, R 1 substituted alkenyl, R 1 substituted alkynyl, R 1 substituted aryl, and R 1 substituted heteroaryl, R 1 the number of R 5. The methyl radical compound according to claim 4, wherein the unsubstituted alkyl group includes a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a neopentyl group, an n-hexyl group, an n-heptyl group, a 2-methylhexyl group, an n-octyl group, an iso-octyl group, a tert-octyl group, a 2-ethylhexyl group, a 3-methylheptyl group, an n-nonyl group, an n-decyl group, a hexadecyl group, an octadecyl group, an eicosyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, or a cyclooctyl group; the unsubstituted alkoxy group is the unsubstituted alkyl group substituted with ≥1 alkoxy group; the unsubstituted alkenyl group includes an ethenyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group, a decenyl group, an undecenyl group, a dodecenyl group, a tridecenyl group, a tetradecenyl group, a pentadecenyl group, a hexadecenyl group, a heptadecenyl group, an octadecenyl group, a nonadecenyl group, an icosapentenyl group, a 2-ethylhexenyl group, an allyl group, or a cyclohexenyl group; the unsubstituted alkynyl group includes an ethynyl group, an iso-propynyl group, a butynyl group, a pentynyl group, a hexynyl group, a heptynyl group, an octynyl group, a nonynyl group, or a decynyl group; The unsubstituted aryl group includes phenyl, biphenyl, terphenyl, quaterphenyl, or quinquephenyl; The unsubstituted heteroaryl group includes benzo-thienocarbazolyl, benzo-furanocarbazolyl, benzo-fluorencarbazolyl, benzanthracenyl, benzophenanthryl, fluorenyl, spiro-bisfluorenyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, indenocarbazolyl, benzimidazolyl, diphenyl-benzimidazolyl, diphenyl-oxadiazolyl, diphenyl-boryl, triphenyl-phosphor-yl, triphenyl-silicon-yl, or tetraphenyl-silicon-yl.

6. The methyl radical compound according to any one of claims 1 to 5, wherein The R 2 The number of carbon atoms in the alkyl moiety of substituted alkyl is 1 to 20. The R 2 The number of carbon atoms in the alkenyl moiety of substituted alkenyl is 2 to 20. The R 2 The number of carbon atoms in the alkynyl moiety of the substituted alkynyl group is 2 to 20. The R 2 The number of carbon atoms in the aromatic hydrocarbon group portion of the substituted aromatic hydrocarbon group is 6 to 40. The R 2 The number of carbon atoms in the aromatic heterocyclic group portion of the substituted aromatic heterocyclic group is 5 to 40.

7. The methyl radical compound according to claim 6, wherein The R 2 In this case, The alkyl group is C1-C20 alkyl group; The alkoxy group is C1-C20 alkoxy group; The cycloalkyl group is C3-C10 cycloalkyl group; The alkenyl group is C2-C20 alkenyl group; The alkynyl group is C2-C20 alkynyl group; The aryl group is C6-C40 aryl group; The heteroaryl group is C5-C40 heteroaryl group.

8. The methyl radical compound according to claim 6, wherein The R1, R2, and R3 independently have any of the structures shown in formulae Ar-1 to Ar-34: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 or .

9. The methyl radical compound according to claim 8, wherein R in any of the formulas Ar-1 through Ar-34 1 each independently is phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, perylenyl, fluoranthenyl, benzofluoranthenyl, naphthacene, pentacene, benzopyrenyl, biphenyl, biphenyl, terphenyl, quaterphenyl, quinquephenyl, triphenyl, fluorenyl, spirobifluorenyl, dihydophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, cis- or trans-monobenzoindenofluorenyl, cis- or trans-dibenzoindenofluorenyl, triindenyl, isotriindenyl, spirotrindenyl, spiroisotriindenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, benzothienocarbazolyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, indolocarbazolyl, indenocarbazolyl, pyridyl, bipyridyl, terpyridyl, quinolyl, isoquinolyl, acridyl, phenanthridyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, phenoxazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthroimidazolyl, pyridimidazolyl, pyrazimidazolyl, quinoximidazolyl, oxazolyl, benzoxazolyl, benzoxadiazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, isoxazolyl, thiazolyl, isothiazolyl, benzothiazolyl, benzothiadiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, quinazolinyl, azafluorenyl, diazanthryl, diazopyrenyl, tetrazaperylenyl, diazanaphthyl, pyrazinyl, phenarseninyl, phenoxaseninyl, phenothiaseninyl, fluorubinyl, naphthidinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, triazolyl, benzotriazolyl, oxadiazolyl, thiadiazolyl, triazinyl, tetrazolyl, tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, pyridopyrrolyl, pyridotriazolyl, xanthenyl, benzofluorocarbazolyl, benzofluorencarbazolyl, N-phenylcarbazolyl, diphenyl-benzimidazolyl, diphenyl-oxadiazolyl, diphenylboron, triphenylphosphine oxide, diphenylphosphine oxide, triphenylsilicon, or tetraphenylsilicon.

10. Use of the methyl radical compound according to any one of claims 1 to 9 in an organic electroluminescence device.

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