Triarylamine-type organic compounds and their use, organic electroluminescent devices

Abstract

The present invention provides a triarylamine-type organic functional compound having a structure represented by formula (I) and its use, [Formula 1] TIFF2026503832000112.tif53164 The A group is a five- or six-membered dibenzo ring structure, and the present invention further provides the use of this compound as a functional material in an organic electroluminescence device.

Description

[Technical Field]

[0001] [CROSS-REFERENCE TO RELATED APPLICATIONS] This application claims priority to a Chinese patent application filed with the China Patent Office on November 30, 2022, bearing application number 202211523216.7 and titled "Triarylamine-type organic compounds and their use in organic electroluminescent devices," the entire contents of which are incorporated herein by reference.

[0002] The present invention relates to the field of organic electroluminescence, in particular to compositions for organic electroluminescence devices, and also to organic electroluminescence devices. [Background technology]

[0003] Organic electroluminescence (OLED) devices are a new display technology that boasts high brightness, fast response, low power consumption, a wide viewing angle, flexibility, a wide temperature range, and simple processing. OLED devices are already widely used in lighting fixtures, smartphones, tablets, and other display panels, and are expanding into large display products such as televisions.

[0004] OLED devices have a sandwich-like structure, consisting of positive and negative electrodes and a layer of organic functional material sandwiched between the two electrodes. When a voltage is applied to the electrodes of an OLED device, electrons and holes are injected into the emissive region, transported there, and then combined to generate excitons, which then emit light. The core of an OLED device is the organic functional material layer, and common organic functional materials that make up this layer include hole-injection materials, hole-transport materials, hole-barrier materials, electron-injection materials, electron-transport materials, electron-barrier materials, emissive hosts, and emissive guests (dyes).

[0005] Common fluorescent emitters primarily emit light using singlet excitons generated when electrons and holes combine, and are still widely used in various OLED products. Some metal complexes (e.g., iridium complexes) can simultaneously emit light using both triplet and singlet excitons. These phosphorescent emitters boast energy conversion efficiencies up to four times higher than conventional fluorescent emitters. Thermally excited delayed fluorescence (TADF) technology promotes the conversion of triplet excitons to singlet excitons, effectively utilizing triplet excitons and achieving relatively high luminous efficiency without the use of metal compounds. Thermally stimulated fluorescence (TASF) technology, on the other hand, employs materials with TADF properties to sensitize emitters through energy transfer, achieving similarly high luminous efficiency.

[0006] The hole transport material has a significant impact on device performance. The hole transport material must have an appropriate HOMO energy level. A suitable energy gap between the hole transport material and the anode favors hole injection and can help reduce operating voltage. Meanwhile, the hole transport material adjusts and controls the carrier transport balance within the device, improving the carrier transition rate of the hole transport material, thereby increasing luminous efficiency and delaying device decay. Currently, products using OLED display technology are commercially available, but further improvements are needed in terms of device efficiency, service life, and other aspects.

[0007] Therefore, in this field, there is a need to develop more types of organic materials with higher performance to improve the performance of organic electroluminescent devices and to provide devices with higher luminous efficiency and lower driving voltage. Furthermore, in recent years, the demand for high refresh rate displays has also increased explosively, and how to improve the response speed of luminescent materials is an issue that needs to be resolved urgently. Summary of the Invention [Problem to be solved by the invention]

[0008] In this field, there is an urgent need to develop organic electroluminescent materials that can improve device luminous efficiency, reduce driving voltage, and extend device life. Electron barrier materials, as important auxiliary light-emitting materials, have attracted significant attention because they can directly affect device performance by effectively improving hole injection and transport and exciton barrier performance. Therefore, the present application aims to provide organic compounds and uses thereof, which are suitable for use in organic electroluminescent devices, particularly as electron barrier layer materials and / or hole transport layer materials, and can improve efficiency, extend device life, and reduce capacitance. [Means for solving the problem]

[0009] As a result of intensive research, the inventors have found that a compound having a structure represented by formula (I) can achieve the object of the present invention. Specifically, the present invention provides the following compound: [ka] In formula (I), the A group is the following group, where the dotted benzene ring represents the presence or absence: [ka] X 1 , X 2 is a single bond, O, S, NR 11 or CR 12 R 13 and X 1 and X 2 is not a single bond at the same time, Ar 1 is a substituted or unsubstituted C10-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group; Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group, L 1 , L 2 are each independently a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group; R 1 , R 2 , R 4 , R 11 , R 12 , R 13 is hydrogen, deuterium, halogen, cyano group, nitro group, hydroxyl group, amino group, substituted or unsubstituted C1-C20 linear alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, C2-C8 alkenyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C1-C20 silanyl group, substituted or unsubstituted C6-C60 arylamino group, substituted or unsubstituted C3-C60 heteroarylamino group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C3-C60 heteroaryl group, and adjacent R 1 or R 2 may or may not be linked to form a ring, R 12 and R 13 may or may not be linked to form a ring, R 3 is a substituted or unsubstituted C4-C20 linear alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, or a substituted or unsubstituted C4-C20 polycyclic alkyl group, n is an integer of 1 to 6, m is an integer of 1 to 3, and p is an integer of 1 to 3; The substituents are each independently selected from at least one of a halogen, a C1-C20 straight or branched alkyl group, a C3-C20 cycloalkyl group, a C3-C20 heterocycloalkyl group, a C1-C10 alkoxy group, a carboxyl group, a nitro group, a cyano group, an amino group, a hydroxyl group, a mercapto group, a C1-C20 alkylsilyl group, a C1-C20 alkylamino group, a C1-C20 alkylamino group, a C6-C30 arylamino group, a C3-C30 heteroarylamino group, a C6-C30 aryloxy group, a C3-C30 heteroaryloxy group, a C6-C60 aryl group, and a C3-C60 heteroaryl group.

[0010] The specific reasons why the compounds of the present invention have excellent performance are not clear, but the following reasons are presumed: First, triarylamine compounds have good hole carrier transport ability, and by introducing a benzene ring or an aromatic group larger than a benzene ring into the adjacent site of the benzene ring in formula (I), it is possible to adjust the magnitude of steric hindrance, and also to more effectively adjust and control the twist of the molecule, thereby reducing the crystallinity of the molecule. Experimental results have shown that the relatively large Ar 1 can more clearly adjust and control the twist of molecules to reduce the crystallinity of molecules, and through the cooperation of groups, can effectively adjust and control the deposition-induced density of molecules, optimize the LUMO and HOMO energy levels, improve the refractive index of molecules, and effectively block the diffusion of excitons into the hole layer, thereby obtaining organic electroluminescent materials with better spatial structure and better thin film deposition morphology, especially applied to the electron barrier layer and / or hole transport layer, which can increase the luminous efficiency of devices, reduce the driving voltage, improve the overall performance of devices, and achieve a relatively large R 3 The steric hindrance by Ar helps to adjust the molecular deposition-induced density to be more favorable for lifetime enhancement. 1 can cooperate with.

[0011] It should be explained that unless otherwise defined below, the semantic meaning of all technical and scientific terms used herein is the same as that commonly understood by those skilled in the art. Reference to technical meanings used herein refers to techniques commonly understood in the field, including any changes in technology or equivalent replacements that are obvious to those skilled in the art. Although it is believed that the following terms are well understood by those skilled in the art, the following definitions are still provided to better interpret the present invention.

[0012] In this specification, the expression Ca to Cb indicates that the number of carbon atoms in the group is a to b, and generally, unless otherwise specified, this number of carbon atoms does not include the number of carbon atoms in substituents. When describing C1 to C30, this includes, but is not limited to, C1, C2, C3, C4, C3, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C22, C24, C26, C28, etc., and no other numerical ranges are described.

[0013] The terms "comprise," "include," "have," "contain," or "relate to," and other variations thereof herein, are inclusive or open-ended and do not exclude other elements or method steps that are not listed.

[0014] In the present invention, unless otherwise specified, the notation of chemical elements generally includes the concept of isotopes with the same chemical properties, for example, the notation of "hydrogen" further includes the concepts of "deuterium" and "tritium" with the same chemical properties, and carbon (C) is 12 C. 13 C, etc., and will not be explained further.

[0015] The heteroatom in the present invention is generally selected from N, O, S, P, Si and Se, and is preferably selected from N, O and S.

[0016] As used herein, the terms "heterocyclic group" and "heterocycle" refer to a saturated (i.e., heterocycloalkyl) or partially unsaturated (i.e., having one or more double and / or triple bonds within the ring) cyclic group in which at least one ring atom is a heteroatom selected from N, O, and S, and the remaining ring atoms are C.

[0017] As used herein, the terms "arylene group" and "aromatic ring" refer to an all-carbon monocyclic or fused-ring polycyclic aromatic group having a conjugated π-electron system. As used herein, the terms "heteroarylene group" and "heteroaromatic ring" refer to a monocyclic, bicyclic, or tricyclic aromatic ring system. As used herein, the term "aralkyl group" preferably refers to an alkyl group substituted with an aryl group or a heteroaryl group, wherein the aryl group, heteroaryl group, and alkyl group are as defined herein.

[0018] As used herein, the term "halogenated" or "halogen" group is defined to include F, Cl, Br, or I.

[0019] The term "substituted" means that one or more (e.g., one, two, three, or four) hydrogens on the designated atom are replaced with the indicated group of choice, provided that the replacement does not exceed the normal valence of the designated atom in its current context, and that such substitution results in the formation of a stable compound. Combinations of substituents and / or variables are permissible only if such combinations result in stable compounds.

[0020] When substituents are described as an "independently selected" group, each substituent is selected independently of the others, and therefore each substituent can be the same as or different from another (other) substituent.

[0021] As used herein, the term "one or more" means one or more, where reasonable, such as two, three, four, five or ten.

[0022] Unless otherwise specified, as used herein, the point of attachment of a substituent can be from any suitable position on the substituent.

[0023] When a substituent bond is depicted as passing through a bond connecting two atoms in a ring, then such substituent may be bonded to any one ring atom in the substitutable ring.

[0024] The term "about" means within ±10%, preferably within ±5%, and more preferably within ±2% of the numerical value.

[0025] In the structural formulas disclosed herein, unless otherwise indicated, TIFF2026503832000004.tif866 and "*" indicate linkage sites, and the representation of a ring structure crossed by a "-" indicates that the linkage site is located at any position on the ring structure where binding is possible.

[0026] The C6-C60 aromatic ring and C3-C60 heteroaromatic ring in the present invention are aromatic groups that satisfy a π-conjugated system unless otherwise specified, and both include monocyclic residues and fused ring residues. The so-called monocyclic residue means that the molecule contains at least one phenyl group, and when the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, examples of which include a phenyl group, a biphenyl group, and a triphenyl group. The fused ring residue means that the molecule contains at least two benzene rings, but the benzene rings are not independent of each other but are fused to each other at their common ring edges, examples of which include a naphthyl group, an anthracenyl group, and a phenanthryl group. The monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When a molecule contains one heteroaryl group and another group (e.g., an aryl group, a heteroaryl group, an alkyl group, etc.), the heteroaryl group and the other group are independent of each other and connected by a single bond, and examples thereof include pyridyl, furyl, and thienyl. A fused cycloheteroaryl group is a group fused with at least one phenyl group and at least one heteroaryl group, or fused with at least two heteroaromatic rings, and examples thereof include quinoline, isoquinoline, benzofuryl, dibenzofuran, benzothienyl, and dibenzothiophene.

[0027] In this specification, the substituted or unsubstituted C6 to C60 aromatic ring is preferably a C6 to C30 aromatic ring, and more preferably an aromatic ring in the group consisting of a phenyl group, a naphthyl group, an anthracenyl group, a benzanthracenyl group, a phenanthryl group, a benzophenanthryl group, a pyrene group, a dimple group, a perylene group, a fluoranthene group, a tetraphenyl group, a pentaphenyl group, a benzopyrene group, a biphenyl group, an azophenyl group, a triphenyl group, a triphenyl group, a tetraphenyl group, a fluorenyl group, a spirodifluorenyl group, a dihydrophenyl group, a dihydropyrenyl group, a tetrahydropyrene group, a cis- or trans-indenefluorenyl group, a tridenyl group, an isotridenyl group, a spirotridenyl group, or a spiroisotridenyl group. Specifically, the biphenyl group is selected from a 2-biphenyl group, a 3-biphenyl group, and a 4-biphenyl group; the triphenyl group includes p-triphenyl-4-yl, p-triphenyl-3-yl, p-triphenyl-2-yl, m-triphenyl-4-yl, m-triphenyl-3-yl, and m-triphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from a 1-anthracenyl group, a 2-anthracenyl group, and a 9-anthracenyl group; the fluorenyl group is selected from a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, and a 9-fluorenyl group; the pyrene group is selected from a 1-pyrene group, a 2-pyrene group, and a 4-pyrene group; and the tetraphenyl group is selected from a 1-tetraphenyl group, a 2-tetraphenyl group, and a 9-tetraphenyl group. Preferred examples of the aromatic ring in the present invention include groups from the group consisting of a phenyl group, a biphenyl group, a triphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a tridenyl group, a fluorenyl group and derivatives thereof, a fluoranthene group, a triphenyl group, a pyrene group, a perylene group, an yl group, and a tetraphenyl group.The biphenyl group is selected from a 2-biphenyl group, a 3-biphenyl group, and a 4-biphenyl group; the triphenyl includes p-triphenyl-4-yl, p-triphenyl-3-yl, p-triphenyl-2-yl, m-triphenyl-4-yl, m-triphenyl-3-yl, and m-triphenyl-2-yl; the naphthyl includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from the group consisting of a 1-anthracenyl group, a 2-anthracenyl group, and a 9-anthracenyl group; and the fluorenyl group is 1- The fluorenyl group derivative is selected from the group consisting of 9,9-dimethylfluorenyl, 9,9-spirodifluorenyl, and benzofluorenyl. The pyrene group is selected from the group consisting of 1-pyrene, 2-pyrene, and 4-pyrene. The tetraphenyl group is selected from the group consisting of 1-tetraphenyl, 2-tetraphenyl, and 9-tetraphenyl. The C10-C60 aryl group in the present invention is an example of a group in which the number of carbon atoms in the aryl group is 10 or more.

[0028] In this specification, the substituted or unsubstituted C6 to C60 aryl group is preferably a C6 to C30 aryl group, and more preferably a group in the group consisting of a phenyl group, a naphthyl group, an anthracenyl group, a benzanthracenyl group, a phenanthryl group, a benzophenanthryl group, a pyrene group, a dimple group, a perylene group, a fluoranthene group, a tetraphenyl group, a pentaphenyl group, a benzopyrene group, a biphenyl group, an azophenyl group, a triphenyl group, a triphenyl group, a tetraphenyl group, a fluorenyl group, a spirodifluorenyl group, a dihydrophenyl group, a dihydropyrenyl group, a tetrahydropyrene group, a cis- or trans-indenefluorenyl group, a tridenyl group, an isotridenyl group, a spirotridenyl group, or a spiroisotridenyl group. Specifically, the biphenyl group is selected from a 2-biphenyl group, a 3-biphenyl group, and a 4-biphenyl group; the triphenyl group includes p-triphenyl-4-yl, p-triphenyl-3-yl, p-triphenyl-2-yl, m-triphenyl-4-yl, m-triphenyl-3-yl, and m-triphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from a 1-anthracenyl group, a 2-anthracenyl group, and a 9-anthracenyl group; the fluorenyl group is selected from a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, and a 9-fluorenyl group; the pyrene group is selected from a 1-pyrene group, a 2-pyrene group, and a 4-pyrene group; and the tetraphenyl group is selected from a 1-tetraphenyl group, a 2-tetraphenyl group, and a 9-tetraphenyl group. Preferred examples of the aryl group in the present invention include groups from the group consisting of a phenyl group, a biphenyl group, a triphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a tridenyl group, a fluorenyl group and derivatives thereof, a fluoranthene group, a triphenyl group, a pyrene group, a perylene group, an yl group, and a tetraphenyl group.The biphenyl group is selected from 2-biphenyl group, 3-biphenyl group and 4-biphenyl group, the triphenyl includes p-triphenyl-4-yl, p-triphenyl-3-yl, p-triphenyl-2-yl, m-triphenyl-4-yl, m-triphenyl-3-yl and m-triphenyl-2-yl, the naphthyl includes 1-naphthyl or 2-naphthyl, the anthracenyl group is selected from the group consisting of 1-anthracenyl group, 2-anthracenyl group and 9-anthracenyl group, and the fluorenyl group is 1-fluorenyl group. The C6 to C60 aryl group of the present invention may be a group in which the above groups are linked and / or fused together via a single bond.

[0029] In this specification, the substituted or unsubstituted C3 to C60 heteroaromatic ring is preferably a C3 to C30 heteroaromatic ring, and may be a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, or the like, and specific examples thereof include a furyl group, a thienyl group, a pyrrolyl group, a pyridyl group, a benzofuryl group, a benzothienyl group, an isobenzofuryl group, an isobenzothienyl group, an indolyl group, an isoindolyl group, a dibenzofuran group, a dibenzothiophene group, a carbazole group and derivatives thereof, a quinoline group, an isoquinoline group, an acridinyl group, a a phenazinyl group, a benzo-5,6-quinoline group, a benzo-6,7-quinoline group, a benzo-7,8-quinoline group, a phenothiazine group, a phenazine group, a pyrazolyl group, an indazolyl group, an imidazolyl group, a benzimidazolyl group, a naphthalimidazole group, a phenanthridine group, a pyridinium group, a pyrazinamizole group, a quinoxazoline group, an oxazolyl group, a benzoxazolyl group, a naphthalocyanine group, an anthranyl group, a phenazolyl group, a 1,2-thienyl group, a 1,3-thienyl group, a benzothienyl group, a pyrazidinyl group, a benzo Pyrazidinyl group, pyrimidinyl group, benzopyrimidinyl group, quinoxalyl group, 1,5-diazaanthranyl group, 2,7-diazabipyrene group, 2,3-diazabipyrene group, 1,6-diazabipyrene group, 1,8-diazabipyrene group, 4,5-diazabipyrene group, 4,5,9,10-tetrazolyl group, pyrazinyl group, phenazine group, phenothiazine group, naphthyl group, azacarbazole group, benzocarboxaline group, phenanthryl group, 1,2,3-triazolyl group, 1,2,4-triazolyl group, benzotriazolyl group, 1,2,3-oxazolyl group, Examples of heteroaromatic rings include those formed by a thiadiazolyl group, a 1,2,4-oxadiazole group, a 1,2,5-oxadiazole group, a 1,2,3-thiadiazoyl group, a 1,2,4-thiadiazoyl group, a 1,2,5-thiadiazoyl group, a 1,3,4-thiadiazoyl group, a 1,3,5-triazine group, a 1,2,4-triazine group, a 1,2,3-triazine group, a tetrazole group, a 1,2,4,5-tetrazine group, a 1,2,3,4-tetrazine group, a 1,2,3,5-tetrazine group, a purine group, a papyzine group, an indazine group, and a benzothiadiazoyl group.Preferred examples of the heteroaromatic ring in the present invention include heteroaromatic rings of a furyl group, a thienyl group, a pyrrolyl group, a benzofuryl group, a benzothienyl group, an isobenzofuryl group, an indolyl group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, and derivatives thereof, and the carbazole group derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole, or indolecarbazole.

[0030] In this specification, the substituted or unsubstituted C3 to C60 heteroaryl group is preferably a C3 to C30 heteroaryl group, more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, or the like, and specific examples thereof include a furyl group, a thienyl group, a pyrrolyl group, a pyridyl group, a benzofuryl group, a benzothienyl group, an isobenzofuryl group, an isobenzothienyl group, an indolyl group, an isoindolyl group, a dibenzofuran group, a dibenzothiophene group, a carbazole group and derivatives thereof, a quinoline group, an isoxazole group, a benzoyl ... acridinyl group, phenazinyl group, benzo-5,6-quinoline group, benzo-6,7-quinoline group, benzo-7,8-quinoline group, phenothiazine group, phenazine group, pyrazolyl group, indazolyl group, imidazolyl group, benzimidazolyl group, naphthalimidazole group, phenanthridine group, pyridinium group, pyrazinamizole group, quinoxazoline group, oxazolyl group, benzoxazolyl group, naphthalocyanine group, anthranyl group, phenazolyl group, 1,2-thienyl group, 1,3-thienyl group, benzothienyl group, pyridinyl ... Razidinyl group, benzopyrazidinyl group, pyrimidinyl group, benzopyrimidinyl group, quinoxalyl group, 1,5-diazaanthranyl group, 2,7-diazabipyrene group, 2,3-diazabipyrene group, 1,6-diazabipyrene group, 1,8-diazabipyrene group, 4,5-diazabipyrene group, 4,5,9,10-tetrazolyl group, pyrazinyl group, phenazine group, phenothiazine group, naphthyl group, azacarbazole group, benzocarboxaline group, phenanthryl group, 1,2,3-triazolyl group, 1,2,4-triazolyl group, benzotriazolyl groups, 1,2,3-oxadiazole groups, 1,2,4-oxadiazole groups, 1,2,5-oxadiazole groups, 1,2,3-thiadiazoyl groups, 1,2,4-thiadiazoyl groups, 1,2,5-thiadiazoyl groups, 1,3,4-thiadiazoyl groups, 1,3,5-triazine groups, 1,2,4-triazine groups, 1,2,3-triazine groups, tetrazole groups, 1,2,4,5-tetrazine groups, 1,2,3,4-tetrazine groups, 1,2,3,5-tetrazine groups, purine groups, papyzine groups, indazine groups, and benzothiadiazoyl groups.Preferred examples of the heteroaryl group in the present invention include a furyl group, a thienyl group, a pyrrolyl group, a benzofuryl group, a benzothienyl group, an isobenzofuryl group, an indolyl group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, and derivatives thereof, and the carbazole derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole, or indolecarbazole. The C3 to C60 heteroaryl group of the present invention may be a group in which the above groups are linked by a single bond and / or fused together.

[0031] The aryl ether group and heteroaryl ether group in the present invention include groups consisting of the above-mentioned aryl group or heteroaryl group and oxygen. The arylamino group and heteroarylamino group in the present invention include groups in which one or two H atoms of the -NH2 group are substituted with the above-mentioned aryl group or heteroaryl group.

[0032] In this specification, the chain alkyl group includes both straight-chain and branched-chain alkyl groups. Examples of C1-C20 alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexylneohexyl, n-heptyl, n-octyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, and 2,2,2-trifluoroethyl groups.

[0033] In this specification, the C3-C20 cycloalkyl group includes a monocyclic alkyl group and a polycyclic alkyl group, and specific examples thereof may be, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, etc.

[0034] The number of carbon atoms in the C2-C20 linear or cyclic alkenyl group is preferably 2 to 10. Specific examples include vinyl groups, 1-propenyl groups, 2-propenyl groups, 2-butenyl groups, 3-butenyl groups, 3-pentenyl groups, 4-pentenyl groups, 1-hexenyl groups, 5-hexenyl groups, 7-octenyl groups, and groups formed from the substituents such as alkyl groups and alkoxy groups that these groups have.

[0035] The number of carbon atoms in the C2-C20 linear or cyclic alkynyl group is preferably 2 to 10. Specific examples of the alkynyl group include ethynyl, 1-propynyl, 2-propynyl, 2-butynyl, 3-butynyl, 3-pentynyl, 4-pentonyl, 1-hexynyl, 5-hexynyl, and groups formed from the substituents such as alkyl and alkoxy groups that these groups have.

[0036] In this specification, the term "alkoxy group" refers to a group consisting of the above-mentioned chain alkyl group and oxygen, or a group consisting of the above-mentioned cycloalkyl group and oxygen.

[0037] Examples of C1 to C20 alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptoxy, octyloxy, nonyloxy, decyloxy, undecyloxy, and dodecyloxy groups, of which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, and isopentyloxy groups are preferred, and methoxy is more preferred.

[0038] In this specification, examples of the C1-C20 silanyl group include a silyl group substituted with any of the C1-C20 alkyl groups listed above, i.e., a group in which one, two, or three hydrogen atoms on the silyl group are substituted with any of the chain alkyl or cycloalkyl groups listed above. Specific examples include methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, and tert-butyldiphenylsilyl groups.

[0039] In a preferred embodiment of the invention, the A group has the following structure: [ka]

[0040] R 1 and R 2 are each independently selected from H, deuterium, a methyl group, a tert-butyl group, a cyclohexane group, a phenyl group, and a naphthyl group, and preferably R 1 and R 2 is H and the adjacent R 1 or R 2 may or may not be linked to form a ring. The A group has easy availability of synthetic raw materials and can well match the HOMO orbital energy level of the entire compound, while the compound has more suitable hole carrier transport properties.

[0041] In a preferred embodiment of the present invention, L 1 and L 2 is a single bond or a phenylene group, and is preferably a single bond; Ar 2 are preferably each independently a substituted or unsubstituted C10-C30 aryl group.

[0042] In a further preferred embodiment of the present invention, the compound has a structure represented by formula (II): [ka] where X1 , X 2 , Ar 2 , Ar 3 , L 1 , L 2 , A, R 4 , R 3 , p has the same meaning as in formula (I), L' is a substituted or unsubstituted C6-C24 aryl group or a substituted or unsubstituted C3-C24 heteroaryl group, and more preferably has the following structure: [ka] R 21 is hydrogen, deuterium, halogen, cyano group, nitro group, hydroxyl group, amino group, substituted or unsubstituted C1-C20 linear alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C1-C20 silanyl group, substituted or unsubstituted C6-C60 arylamino group, substituted or unsubstituted C3-C60 heteroarylamino group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C3-C60 heteroaryl group, Ar' is preferably a substituted or unsubstituted structure as follows: [ka]

[0043] The substituents are each independently selected from at least one of halogen, a C1-C20 straight or branched alkyl group, a C3-C20 cycloalkyl group, a C3-C20 heterocycloalkyl group, a C1-C10 alkoxy group, a carboxyl group, a nitro group, a cyano group, an amino group, a hydroxyl group, a mercapto group, a C1-C20 alkylsilyl group, a C1-C20 alkylamino group, a C1-C20 alkylamino group, a C6-C30 arylamino group, a C3-C30 heteroarylamino group, a C6-C30 aryloxy group, a C3-C30 heteroaryloxy group, a C6-C60 aryl group, and a C3-C60 heteroaryl group.

[0044] In a preferred embodiment of the present invention, R 3 is a substituent having a tertiary carbon group, and is preferably a substituted or unsubstituted group having the following structure: [ka] R 4 is H, a phenyl group, a biphenyl group, or a naphthyl group, and is preferably H. Based on a large amount of experimental data, the inventors have found that by introducing an aryl group or a heteroaryl group into the adjacent position of the benzene ring in formula (I), Ar 1 By combining this with a substituent with a relatively large conjugation, it is possible to prevent electrons from entering the transport layer, while at the same time moderately reducing the capacitance of the compound after film formation, which has been shown to be advantageous for improving the rapid response performance of devices.

[0045] In a preferred embodiment of the present invention, Ar 2 is the substituted or unsubstituted structure: [ka] Particularly preferably, the biphenyl group can make the photoelectric performance of the compound better.

[0046] L 2 is most preferably a single bond, and in a preferred embodiment of the present invention, Ar 3 is selected from the following substituted or unsubstituted groups: [ka] TIFF2026503832000012.tif126164

[0047] Here, the wavy line TIFF2026503832000013.tif866 is a linking moiety, and A1 to A3 are substituted or unsubstituted C1 to C30 linear alkyl groups, C3 to C20 cycloalkyl groups, C6 to C20 aryl groups, C5 to C20 heteroaryl groups, or combinations thereof. If the above groups have substituents, the substituents are selected from one or a combination of at least two of the following: C1 to C12 linear alkyl groups, C3 to C12 cycloalkyl groups, C2 to C10 alkenyl groups, C1 to C10 alkoxy or thioalkoxy groups, C6 to C30 arylamino groups, C3 to C30 heteroarylamino groups, C6 to C30 aryl groups, and C3 to C30 heteroaryl groups. In these compounds, phenyl or substituted phenyl groups are preferred because, if the steric hindrance of the molecule is sufficient, the overall molecular weight becomes too large, making synthesis more difficult.

[0048] Specific compounds of the present invention preferably have one of the structures shown below, but are not limited to these compounds: [ka] TIFF2026503832000015.tif225167TIFF2026503832000016.tif242169TIFF2026503832000017.tif240166TIFF2026503832000018.tif240168TIFF2026503832000019.tif226167TIFF2026503832000020.tif240168TIFF2026503832000021.tif250167TIFF2026503832000022.tif236167TIFF2026503832000023.tif234167TIFF2026503832000024.tif238166TIFF2026503832000025.tif239167TIFF2026503832000026.tif238167TIFF2026503832000027.tif237167TIFF2026503832000028.tif234168TIFF2026503832000029.tif238167TIFF2026503832000030.tif238167TIFF2026503832000031.tif240168TIFF2026503832000032.tif234168TIFF2026503832000033.tif238168TIFF2026503832000034.tif239167TIFF2026503832000035.tif239168TIFF2026503832000036.tif237165TIFF2026503832000037.tif242168TIFF2026503832000038.tif238168TIFF2026503832000039.tif236167TIFF2026503832000040.tif234167

[0049] The second object of the present invention is to provide the use of the compound according to the first object.The compound of the present invention can be applied not only to organic electroluminescence devices, but also to other types of organic electronic devices, including organic field-effect transistors, organic thin-film solar cells, information labels, electronic artificial skin sheets, sheet-type scanners, or electronic paper.Preferably, the compound is used as an electron barrier layer material in the organic electroluminescence devices.

[0050] A third object of the present invention is to provide an organic electroluminescent device, which comprises a first electrode, a second electrode, and at least one organic layer interposed between the first electrode and the second electrode, and the organic layer comprises at least one compound according to one of the objects.

[0051] Preferably, the organic layer comprises an electron barrier layer, and the electron barrier layer comprises at least one compound according to one of the objects. [Effects of the Invention]

[0052] Superior advantages of the present invention over conventional techniques: The organic compound according to the present application has the structure shown in Formula I. By designing the molecular structure, the presence of a relatively large aryl or heteroaryl group (having 10 or more carbon atoms) between N and the alkyl, cycloalkyl, or polycyclic alkyl group can effectively control the molecular steric structure and enhance the molecular stacking-induced density, while also improving the molecular refractive index and performance. The presence of a dibenzoheterocycle in the group connected to N provides a more planar structure, reducing the molecular crystallinity and enhancing the molecular stacking-induced density. However, the presence of an alkyl, cycloalkyl, or polycyclic alkyl group can effectively block exciton diffusion to holes, thereby improving device stability and lifetime. The simultaneous presence of substituents at the ortho and meta positions of the benzene ring connected to N increases the spatial steric hindrance of the compound, favoring a shallower LUMO energy level, thereby further inhibiting exciton diffusion to the hole transport layer and improving device performance. Further adjustment and control can further improve transport efficiency, achieving the goals of lower voltage and extended lifetime. In addition, the device capacitance of the present invention is lower, and in display applications, lowering the capacitance of the OLED device shortens the charge / discharge process, increases the brightness of the first frame during video display, and helps prevent poor display effects such as smear. Furthermore, the preparation process of the compound of the present invention is simple and easy to operate, and raw materials are readily available, making it suitable for mass production. As can be seen from the experimental data of the present invention described below, the new organic material of the present invention is an organic light-emitting functional material with excellent performance and is significantly improved over conventional electron barrier materials in organic electroluminescent devices, and has broad application prospects.

[0053] There is a demand for electron barrier materials to have similar material properties to hole injection materials and hole transport materials, and therefore the compound of the present invention may be used as a hole injection material or a hole transport material.

[0054] It should be noted that although the present application describes the possible role of each group / feature for the sake of convenience, it does not imply that these groups / features act in isolation. In fact, the reason for the good performance is essentially the optimal combination of the whole molecule, and is the result of the synergistic effects of each group, not the effect of a single group. [Brief explanation of the drawings]

[0055] [Figure 1] FIG. 1 is a diagram showing potential values ​​of specific compounds and comparisons in examples. DETAILED DESCRIPTION OF THE INVENTION

[0056] The technical solutions of the present invention will be further described below by way of specific embodiments. Those skilled in the art will appreciate that the above examples are only intended to aid in the understanding of the present invention, and should not be construed as specific limitations on the present invention.

[0057] General synthesis methods for compounds The compounds of the present invention can be synthesized by known methods. For example, a typical synthesis route for an organic compound having a structure represented by Formula I in the present application is as follows: [ka]

[0058] where each symbol has the same meaning as in Formula I, Pd2(dba)3 represents tri(dibenzylacetone)dipalladium(0), IPr.HCl represents 1,3-bis(2,6-diisopropylphenyl)chlorinated imidazolium, NaOBu-t represents sodium tert-butanol, and (t-Bu)3P represents tri-tert-butylphosphine.

[0059] The preparation of organic compounds described in this application includes, but is not limited to, the above-mentioned methods, and organic compounds represented by Formula I synthesized by those skilled in the art using other methods also fall within the scope of protection of this application. For more specific synthesis methods, reference may be made to the synthesis examples described below. Those skilled in the art can summarize and specifically implement other similar synthesis methods based on the specific operation methods of the synthesis examples.

[0060] Embodiments of the Device of the Present Invention The organic electroluminescent device (OLED) of the present invention is characterized by containing the compound of the present invention as a functional material. It is known that the OLED comprises an organic material layer located between a first electrode and a second electrode, and between the electrodes. This organic material can also be divided into multiple regions. For example, this organic material layer may comprise a hole transport region, a light-emitting layer, and an electron transport region.

[0061] In a specific embodiment, a substrate can be used under the first electrode or over the second electrode. The substrate is made of glass or a polymer material that has mechanical strength, thermal stability, waterproofness, and excellent transparency. Thin film transistors (TFTs) may be attached to the substrate for a display.

[0062] The first electrode may be formed by sputtering or depositing a material for the first electrode on a substrate. When the first electrode is an anode, transparent conductive oxide materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO), zinc oxide (ZnO), and any combination thereof can be used. When the first electrode is a cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof can be used.

[0063] The organic material layer can be formed on the electrode by methods such as vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic material layer may be an organic small molecule, an organic large molecule and a polymer, or a combination thereof.

[0064] The hole transport region is located between the anode and the light-emitting layer. The hole transport region may be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region may be a multi-layer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron barrier layer (EBL), where the HIL is between the anode and the HTL, and the EBL is between the HTL and the light-emitting layer.

[0065] The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polystyrene, polyaniline / dodecylbesylate (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), aromatic amine derivatives, compounds represented by HT-1 to HT-51 shown below, or any combination thereof. [ka] TIFF2026503832000043.tif201168TIFF2026503832000044.tif128166

[0066] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of multiple compounds. For example, the hole injection layer may employ one or more of the compounds HT-1 to HT-51 above, or may employ one or more of the compounds HI-1 to HI-3, or may employ one or more of the compounds HT-1 to HT-51 doped with one or more of the compounds HI-1 to HI-3 below. [ka]

[0067] The light-emitting layer may contain a light-emitting dye (i.e., a dopant) capable of emitting light of different wavelength spectrums and may also contain a host material. The light-emitting layer may be a monochromatic light-emitting layer that emits a single color, such as red, green, or blue. Multiple monochromatic light-emitting layers of different colors may be arranged in a plane according to a pixel pattern or may be stacked to form a color light-emitting layer. When different color light-emitting layers are stacked, they may be separated from each other or connected to each other. The light-emitting layer may be a single color light-emitting layer that can simultaneously emit different colors, such as red, green, and blue. Depending on the technology, the light-emitting layer material can be made of different materials, such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescent materials. An OLED device can use a single light-emitting technology or a combination of multiple light-emitting technologies. The different light-emitting materials for these technologies can emit light of the same color or different colors. In one embodiment of the present invention, the light-emitting layer employs fluorescent electroluminescence technology, and the fluorescent host material of the light-emitting layer may be selected from, but is not limited to, one or more combinations of BFH-1 to BFH-17 listed below. [ka]

[0068] In one embodiment of the present invention, the light-emitting layer employs fluorescent electroluminescence technology, and the fluorescent dopant of the light-emitting layer may be selected from, but is not limited to, one or more combinations of BFD-1 to BFD-24 listed below. [ka] TIFF2026503832000048.tif182168

[0069] In one embodiment of the present invention, the light-emitting layer employs phosphorescent electroluminescence technology, and the light-emitting layer host material is selected from, but not limited to, one or more combinations of PH-1 to PH-85. [ka] TIFF2026503832000050.tif239168TIFF2026503832000051.tif220168TIFF2026503832000052.tif71166

[0070] In one embodiment of the present invention, the light-emitting layer employs phosphorescent electroluminescence technology, and the phosphorescent dopant in the light-emitting layer may be selected from, but is not limited to, one or more combinations of GPD-1 to GPD-47 listed below. [ka] TIFF2026503832000054.tif201164

[0071] In one embodiment of the present invention, the light-emitting layer employs phosphorescent electroluminescence technology, and the phosphorescent dopant in the light-emitting layer may be selected from, but is not limited to, one or more combinations of RPD-1 to RPD-28 listed below. [ka]

[0072] In one embodiment of the present invention, the light-emitting layer employs phosphorescent electroluminescence technology, and the phosphorescent dopants in the light-emitting layer may be selected from, but are not limited to, one or more combinations of YPD-1-YPD-11 listed below. [ka]

[0073] In one embodiment of the present invention, the light-emitting layer employs thermally activated delayed fluorescence technology, and the host material of the light-emitting layer is selected from, but not limited to, one or a combination of the above-mentioned PH-1 to PH-85.

[0074] In one embodiment of the present invention, the light-emitting layer employs thermally activated delayed fluorescence technology, and the fluorescent dopant of the light-emitting layer may be selected from, but is not limited to, one or more combinations of TDE1-TDE37 listed below. [ka] TIFF2026503832000058.tif129164

[0075] In one embodiment of the present invention, an electron barrier layer (EBL) is located between the hole transport layer and the light emitting layer. The electron barrier layer can be, but is not limited to, one or more of the compounds HT-1 to HT-51 described above, or one or more of the compounds PH-47 to PH-77 described above, or a mixture of one or more of the compounds HT-1 to HT-51 and one or more of the compounds PH-47 to PH-77.

[0076] The OLED organic material layer may further include an electron transport region between the light-emitting layer and the cathode. The electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one type of compound, or a single-layer electron transport layer containing multiple types of compounds. The electron transport region may also be a multi-layer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole barrier layer (HBL).

[0077] In one embodiment of the present invention, the electron transport layer material may be selected from, but is not limited to, one or more combinations of ET-1 to ET-73 listed below. [ka] TIFF2026503832000060.tif254165TIFF2026503832000061.tif172168

[0078] In one embodiment of the present invention, a hole barrier layer (HBL) is located between the electron transport layer and the light emitting layer, and the hole barrier layer can be, but is not limited to, one or more of the compounds ET-1 to ET-73, or one or more of the compounds PH-1 to PH-46, or a mixture of one or more of the compounds ET-1 to ET-73 and one or more of the compounds PH-1 to PH-46.

[0079] The device may further include an electron injection layer between the electron transport layer and the cathode, where the electron injection layer materials include, but are not limited to, one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Yb, Li, or Ca.

[0080] Example Synthesis Example 1 Mass spectrometry data in the following synthesis examples was obtained by testing a ZAB-HS mass spectrometer manufactured by Micromass, UK.

[0081] Synthesis of compound P2 [ka]

[0082] In a 1000 mL single-neck bottle, 15.00 g of M1, 13.50 g of 4-bromo-4'-tert-butylbiphenyl, 0.43 g of dibenzylacetone)dipalladium(0) (Pd2(dba)3), 0.40 g of 1,3-bis(2,6-diisopropylphenyl)chlorinated imidazolium (IPr.HCl), 13.45 g of sodium tert-butanol (NaOBu-t), and 300 mL of toluene were added. Nitrogen gas was evacuated three times, and the reaction was heated to 90 °C and reacted for 5 h. After completion of the reaction, the reaction mixture was cooled to room temperature, separated, and the organic phase was purified twice using a silica gel column. The organic phase was concentrated, methanol was added, and the mixture was refluxed and stirred for 1 h. It was then suction filtered to obtain a pale yellow powder, P2-1, which was then recrystallized in ethyl acetate to obtain 20.50 g of pure product. P2-1: theoretical m / z value: 529; measured m / z value: 530.

[0083] In a 1000 mL single-neck bottle, 20.50 g of P2-1, 12.69 g of 2-bromo-9,9-dimethylfluorenyl, 0.35 g of Pd2(dba)3, 0.2 mL of tert-butylphosphine (t-Bu)3P, 11.16 g of sodium tert-butanol, and 300 mL of toluene were added. Nitrogen gas was evacuated three times, and the reaction was heated to 110 °C and reacted for 5 h. After completion of the reaction, the reaction mixture was cooled to room temperature, separated, and the organic phase was purified twice using a silica gel column. The organic phase was concentrated, methanol was added, and the mixture was refluxed and stirred for 1 h. It was then suction filtered to obtain a pale yellow powder, P2, which was then recrystallized three times using ethyl acetate to obtain 18.30 g of pure product. Organic compound P2: theoretical m / z: 721; observed m / z: 722.

[0084] (Synthesis Example 2-14) The process of Synthesis Example 2-14 is the same as that of Synthesis Example 1, except that M1 in Synthesis Example 1 is replaced with an intermediate represented by M-NH2, and 4-bromo-4'-tert-butylbiphenyl is replaced with R 3 -Ar 1 The difference is that 2-bromo-9,9-dimethylfluorenyl was converted into the intermediate represented by A-Br, as shown in Table 1. [Table 1] TIFF2026503832000064.tif231165TIFF2026503832000065.tif93165

[0085] Device Example The following device experiments were carried out based on the specific compounds synthesized above. In the following device experiments, conventional compounds similar to the compounds of the present invention were introduced for technical comparison. However, these comparative compounds (compounds numbered CCP) are all conventional technologies, and their synthesis methods will not be further described.

[0086] Example 1 The manufacturing process of the organic electroluminescent device of this example is as follows: The fabrication method of the organic electroluminescence device is as follows: a glass plate coated with an ITO transparent conductive layer is ultrasonically treated in a commercial detergent, rinsed in deionized water, ultrasonically removed oil in a mixed solvent of acetone / ethanol, baked in a clean environment until the moisture is completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam on the surface. The above glass substrate with an anode is placed in a vacuum chamber, and a <1 × 10 -5The vacuum was drawn to 100 Pa, and the following layers were sequentially deposited on the anode layer by vacuum thermal evaporation: 10 nm of a mixture of compounds HT-4 and HI-3 (97 / 3, w / w) as a hole injection layer, 60 nm of compound HT-4 as a hole transport layer, 35 nm of the present organic compound P2 as an electron barrier layer, 40 nm of a ternary mixture of compounds PH-61, PH-3, and GPD-12 (100:100:20, w / w) as an emissive layer, 5 nm of ET-23 as a hole barrier layer, 25 nm of a mixture of compounds ET-69 and ET-57 (50 / 50, w / w) as an electron transport layer, 1 nm of LiF as an electron injection layer, and 150 nm of metallic aluminum as a cathode. The total deposition rate of all the organic layers and LiF was controlled to 0.1 nm / s, and the deposition rate of the metal electrode was controlled to 1 nm / s.

[0087] (Examples 2-6) The organic electroluminescence device differs from Example 1 only in that the electron barrier layer material organic compound P2 is replaced with P14, P57, P87, P553, or P546.

[0088] (Comparative Examples 1-3) The organic electroluminescence device differs from Example 1 only in that the electron barrier layer material organic compound P2 is replaced with CCP-1, CCP-2, or CCP-3. [ka]

[0089] The organic electroluminescent devices according to Examples 2-6 and Comparative Examples 1-3 were subjected to the following performance tests: the current efficiency and device lifespan of the organic electroluminescent devices according to Examples 2-6 and Comparative Examples 1-3 were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the voltage was increased at a rate of 0.1 V per second, and the current density was measured when the luminance of the organic electroluminescent device reached 10,000 cd / m². The ratio of luminance to current density was the current efficiency.

[0090] The life test for the LT97 is as follows: 2 ) was maintained, and the time it took for the luminance of the organic electroluminescence device to decay to 97% of the initial luminance was measured in hours.

[0091] The obtained data is summarized in Table 2, where each performance index of Comparative Example 1 is set to 100, and the performance of the other devices is expressed as a relative value to Comparative Example 1. [Table 2]

[0092] In accordance with the data in Table 2, it was found that the compounds of the present invention can be used in organic electroluminescent devices to further improve current efficiency and extend the service life of the device. P2, P57, and P87 are superior to CCP-1, P14 to CCP-2, and P553 to CCP-3. The presence of a relatively large aryl or heteroaryl group (having 10 or more carbon atoms) between N and the alkyl, cycloalkyl, or polycyclic alkyl group can effectively adjust the molecular conformation and improve the stacking-induced density of the molecule compared to a benzene ring, while also improving the refractive index of the molecule, thereby further improving the performance of devices fabricated using them.

[0093] Example 7 The organic electroluminescence device had the same device structure and fabrication process as in Example 1, but the hole transport layer material was replaced with 105 nm HT-28, and the electron barrier layer material organic compound P2 was replaced with P6.

[0094] Examples 8-10 The organic electroluminescence device had the same device structure and fabrication process as in Example 7, but the electron barrier layer organic compound P6 was replaced with P23, P30, and P274.

[0095] (Comparative Example 4-5) This organic electroluminescence device differs from Example 7 only in that the electron barrier layer material organic compound P2 is replaced with CCP-4 and CCP-5. [ka]

[0096] The organic electroluminescent devices according to Examples 7-10 and Comparative Examples 4-5 were subjected to the following performance tests: the driving voltage and device lifespan of the organic electroluminescent devices according to Examples 7-10 and Comparative Examples 4-5 were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the voltage was increased at a rate of 0.1 V per second, and the driving voltage was measured when the luminance of the organic electroluminescent device reached 10,000 cd / m2.

[0097] The life test for the LT97 is as follows: 2 ) was maintained, and the time it took for the luminance of the organic electroluminescence device to decay to 97% of the initial luminance was measured in hours.

[0098] The obtained data is summarized in Table 3, where each performance index of Comparative Example 4 is set to 100, and the performance of the other devices is expressed as a relative value to Comparative Example 4. [Table 3]

[0099] Based on the data in Table 3, it can be seen that the compounds of the present invention, when used in organic electroluminescent devices, are more advantageous in reducing driving voltage and extending device service life. Compared with CCP-4, P6, P23, and P30, and compared with CCP-5, P274 has a higher efficiency than CCP-5. When a five- or six-membered dibenzo-heterocycle is present in the group connected to the N-atom, this may be due to the dibenzo-heterocycle having a more planar structure, reducing molecular crystallinity and increasing molecular stacking-induced density. At the same time, further adjustment and control can further improve transport efficiency, achieving the goals of lowering voltage and extending device service life.

[0100] Example 11 This is a top-emission organic electroluminescence device, and its device structure and fabrication process are the same as those of Example 11, except that the hole transport layer material was replaced with 105 nm of HT-28, the electron injection layer material LiF was replaced with 20 nm of Mg:Ag (10:1) alloy, the cathode material Al was replaced with 70 nm of Ag, and the electron barrier layer material organic compound P2 was replaced with P165.

[0101] Example 12 This organic electroluminescence device differs from that of Example 11 only in that the organic compound P165 used as the electron barrier layer material is replaced with P348.

[0102] (Comparative Examples 6-7) This organic electroluminescence device differs from that of Example 11 only in that the organic compound P165 used as the electron barrier layer material is replaced with CCP-6 and CCP-7. [ka]

[0103] The organic electroluminescent devices according to Examples 11-12 and Comparative Examples 6-7 were subjected to the following performance tests: the current efficiency and device lifespan of the organic electroluminescent devices according to Examples 11-12 and Comparative Examples 6-7 were measured using a digital source meter and a luminance meter at the same luminance. Specifically, the voltage was increased at a rate of 0.1 V per second, and the current density was measured when the luminance of the organic electroluminescent device reached 10,000 cd / m². The ratio of luminance to current density was the current efficiency.

[0104] The life test for the LT97 is as follows: 2 ) was maintained, and the time it took for the luminance of the organic electroluminescence device to decay to 97% of the initial luminance was measured in hours.

[0105] The obtained data is summarized in Table 4, where each performance index of Comparative Example 6 is set to 100, and the performance of the other devices is expressed as a relative value to Comparative Example 6. [Table 4]

[0106] In accordance with the data in Table 4, it can be seen that the compounds of the present invention can be used in organic electroluminescent devices to further improve efficiency and extend the service life of the device. Compared with CCP-6, P165 and P348, compared with CCP-7, have substituents at the ortho and meta positions of the benzene ring connected to the N atom, which increases the spatial steric hindrance of the compounds compared with the ortho and para positions of the benzene ring connected to the N atom, and is advantageous in shallowing the LUMO energy level, thereby further preventing exciton diffusion to the hole layer and improving device performance.

[0107] Example 13 A top-emission organic electroluminescence device was used, employing a glass substrate plated with an Ag / ITO emission layer. The cleaning process was the same as in Example 1, and the deposition process for each layer material was also the same. The hole injection layer, hole barrier layer, and electron transport layer of the device remained unchanged, except that the hole transport layer material was replaced with 105 nm of HT-28, the electron injection layer material was replaced with 1 nm of yttrium (Yb), and the cathode material Al was replaced with 100 nm of Mg:Ag (1:10) alloy. An 85 nm layer of HT-21 was further deposited on the cathode as a CPL, and the electron barrier layer material remained the same as in Example 1.

[0108] Examples 14-18 The organic electroluminescence device has the same structure and fabrication process as that of Example 13, except that the electron barrier layer materials are replaced with P6, P23, P30, P72, and P589.

[0109] (Comparative Examples 8-9) The organic electroluminescence device had the same structure and fabrication process as in Example 13, but the electron barrier layer material was replaced with CCP-8 and CCP-9. [ka]

[0110] The LT97 life test performed on the organic electroluminescent devices according to Examples 13-18 and Comparative Examples 8-9 above was as follows: 2 ) and measured the time in hours until the luminance of the organic electroluminescent device decayed to 97% of its initial luminance. At the same time, a capacitance test was performed using the AC impedance method to measure the change in capacitance of the device when the bias voltage was changed from -2V to 5V. The results are shown in Figure 1, and the relative peak capacitance values ​​are summarized in Table 5. The obtained data is summarized in Table 5, where the performance index of Comparative Example 8 is set to 100 and the performance of the other devices is expressed as a relative value to Comparative Example 8. [Table 5]

[0111] Based on the data in Table 5, the compounds of the present invention can be used in organic electroluminescent devices to further extend the device's service life. Compared to CCP-8, P2 and P72, and P589, compared to CCP-9, have different alkyl groups, which can effectively block exciton diffusion to holes, thereby improving device stability and extending device life. Furthermore, the capacitance of the devices of the present invention was lower than that of the comparative examples. As can be seen from Figure 1, P2, P72, and P589 exhibited significantly lower capacitance than CCP-8 and CCP-9. In display applications, reducing the capacitance of OLED devices shortens the charge / discharge process, increases the brightness of the first frame during video display, and helps prevent poor display effects such as smearing, which is beneficial for improving screen refresh rates.

[0112] Example 19 The organic electroluminescent device had the same structure and fabrication process as in Example 1, except that the emissive layer material was replaced with a 40 nm binary mixture of compounds PH-34:RPD-8 (97 / 3, w / w), and the thickness of the electron barrier layer material P2 was increased to 60 nm.

[0113] As described above, the present invention provides a high-performance electron barrier layer material that can be applied to green light-emitting devices, effectively reducing the device driving voltage, improving device efficiency, and extending device life, while also providing lower capacitance.

[0114] The applicant declares that the present invention describes the compounds of the present invention and their uses through the above examples, but the present invention is not limited to the above examples, and does not mean that the present invention cannot be carried out without relying on the above examples. As is obvious to those skilled in the art, any improvements of the present invention, equivalent replacement of each raw material of the product of the present invention, addition of auxiliary ingredients, selection of specific embodiments, etc. are all within the protection scope and disclosure of the present invention.

[0115] Although the present invention has been described in detail in the above examples, the present invention is not limited to the above detailed methods, and does not mean that the present invention cannot be carried out without relying on the above detailed methods. As will be apparent to those skilled in the art, any improvements to the present invention, equivalent replacement of each raw material of the product of the present invention, addition of auxiliary ingredients, selection of specific embodiments, etc., are all within the scope of protection and disclosure of the present invention.

Claims

1. A triarylamine-type organic compound having the formula (I): 【Chemistry 1】 It has a structure represented by In formula I, the group A is: 【Chemistry 2】 X １ , X ２ is a single bond, O, S, NR １１ or CR １２ R １３ and X １ and X ２ is not a single bond at the same time, Ar １ is a substituted or unsubstituted C10-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group; Ar ２ and Ar ３ are each independently a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group, L １ , L ２ are each independently a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group; R １ , R ２ , R ４ , R １１ , R １２ , R １３ is hydrogen, deuterium, halogen, cyano group, nitro group, hydroxyl group, amino group, substituted or unsubstituted C1-C20 linear alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C2-C8 alkenyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C1-C20 silanyl group, substituted or unsubstituted C6-C60 arylamino group, substituted or unsubstituted C3-C60 heteroarylamino group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C3-C60 heteroaryl group, and an adjacent R １ or R ２ may or may not be linked to form a ring, and R １２ and R １３ may or may not be linked to form a ring, R ３ is a substituted or unsubstituted C4-C20 chain alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, or a substituted or unsubstituted C4-C20 polycyclic alkyl group, n is an integer from 1 to 6, m is an integer from 1 to 3, and p is an integer from 1 to 3; the substituents are each independently selected from at least one of a halogen, a C1-C20 straight or branched alkyl group, a C3-C20 cycloalkyl group, a C3-C20 heterocycloalkyl group, a C1-C10 alkoxy group, a carboxyl group, a nitro group, a cyano group, an amino group, a hydroxyl group, a mercapto group, a C1-C20 alkylsilyl group, a C1-C20 alkylamino group, a C1-C20 alkylamino group, a C6-C30 arylamino group, a C3-C30 heteroarylamino group, a C6-C30 aryloxy group, a C3-C30 heteroaryloxy group, a C6-C60 aryl group, or a C3-C60 heteroaryl group; A triarylamine-type organic compound, characterized in that "*" represents a linking site, and the representation of a ring structure crossed by "-" indicates that the linking site is located at any position on the ring structure where bonding is possible.

2. The A group has the following structure: 【Transformation 3】 R １ , R ２ , m and n have the same meanings as in formula (I), Preferably, R １ and R ２ are each independently selected from H, deuterium, methyl, tert-butyl, cyclohexane, phenyl, and naphthyl; More preferably, R １ and R ２ The triarylamine-type organic compound according to claim 1, wherein is H.

3. L １ and L ２ represents a single bond or a phenylene group, and is preferably a single bond; Preferably, Ar ２ are each independently a substituted or unsubstituted C10-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group.

4. Formula (II) 【Chemistry 4】 It has a structure represented by Here, X １ , X ２ , Ar ２ , Ar ３ , L １ , L ２ , A, R ４ , R ３ , p has the same meaning as in formula (I), L' is a substituted or unsubstituted C6-C24 aryl group, or a substituted or unsubstituted C3-C24 heteroaryl group, and more preferably has the following structure: 【Transformation 5】 R ２１ is hydrogen, deuterium, halogen, cyano group, nitro group, hydroxyl group, amino group, substituted or unsubstituted C1-C20 linear alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C1-C20 silanyl group, substituted or unsubstituted C6-C60 arylamino group, substituted or unsubstituted C3-C60 heteroarylamino group, substituted or unsubstituted C6-C60 aryl group, or substituted or unsubstituted C3-C60 heteroaryl group; Ar' is a substituted or unsubstituted group having the following structure: 【Transformation 6】 The triarylamine-type organic compound according to any one of claims 1 to 3, wherein the substituents are each independently selected from at least one of a halogen, a C1-C20 linear or branched alkyl group, a C3-C20 cycloalkyl group, a C3-C20 heterocycloalkyl group, a C1-C10 alkoxy group, a carboxyl group, a nitro group, a cyano group, an amino group, a hydroxyl group, a mercapto group, a C1-C20 alkylsilyl group, a C1-C20 alkylamino group, a C1-C20 alkylamino group, a C6-C30 arylamino group, a C3-C30 heteroarylamino group, a C6-C30 aryloxy group, a C3-C30 heteroaryloxy group, a C6-C60 aryl group, and a C3-C60 heteroaryl group.

5. R ３ is a substituent having a tertiary carbon group, and is preferably a substituted or unsubstituted group having the following structure: 【Transformation 7】 R ４ The triarylamine-type organic compound according to any one of claims 1 to 4, wherein is H, a phenyl group, a biphenyl group, or naphthyl, and is preferably H.

6. Ar ２ is a substituted or unsubstituted structure of: 【Transformation 8】 5. The triarylamine-type organic compound according to claim 1, wherein

7. Ar ３ is selected from the following substituted or unsubstituted groups: 【Chemistry 9】 【change】 Here, the wavy line 【change】 is a linking moiety, and A1 to A3 each independently represent one or a combination of at least two of a substituted or unsubstituted C1 to C30 linear alkyl group, a C3 to C20 cycloalkyl group, a C6 to C20 aryl group, and a C5 to C20 heteroaryl group; The triarylamine-type organic compound according to any one of claims 1 to 6, wherein, when a substituent is present in the group, the substituent is selected from one or a combination of at least two of a C1 to C12 chain alkyl group, a C3 to C12 cycloalkyl group, a C2 to C10 alkenyl group, a C1 to C10 alkoxy group or thioalkoxy group, a C6 to C30 arylamino group, a C3 to C30 heteroarylamino group, a C6 to C30 aryl group, and a C3 to C30 heteroaryl group.

8. The triarylamine-type organic compound according to claim 1, characterized in that it has any one of the structures shown below. 【Chemistry 10】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

9. 2. The triarylamine-type organic compound according to claim 1, wherein the triarylamine-type organic compound is selected from at least one of P2, P6, P14, P23, P30, P57, P72, P87, P165, P274, P348, P553, P546, P553, and P589.

10. Use of the triarylamine-type organic compound according to any one of claims 1 to 9 as a functional material in an organic electronic device, the organic electronic device comprising an organic electroluminescence device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet-type scanner, or electronic paper, preferably as an electron barrier layer material in an organic electroluminescence device.

11. An organic electroluminescent device comprising a first electrode, a second electrode, and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer contains the compound according to any one of claims 1 to 9; Preferably, the light-emitting functional layer includes at least one of an electron barrier layer, a hole transport layer, or a hole injection layer, and the at least one of the electron barrier layer, the hole transport layer, or the hole injection layer includes the compound according to any one of claims 1 to 9.

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