An anthracene derivative containing a boron atom and its application

Abstract

The present invention relates to an anthracene derivative containing a boron atom, an organic electroluminescent material, a light-emitting device, and a consumer product. The anthracene derivative described in the present invention has a novel organic electroluminescent compound in which anthracene and a boron atom form a macrocyclic planar structure. The large planar anthracene derivative realizes the separation of HOMO and LUMO through the resonance effect between boron-nitrogen and boron-oxygen, thereby realizing the TADF effect and achieving a shorter emission wavelength compared with existing compounds. On the other hand, by introducing different substituents on the rigid skeleton, further adjustment of the delayed fluorescence lifetime and full width at half maximum can be achieved.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic electroluminescence, and particularly relates to an anthracene derivative containing a boron atom, an organic electroluminescent material, a light-emitting device, and a consumer product. Background Art

[0002] Most of the substances used in organic electroluminescent elements are pure organic substances or organometallic complexes formed by organic substances and metals, which can be classified into hole injectors, hole transporters, light emitters, electron transporters, electron injectors, etc. according to their uses. Here, organic substances with relatively small ionization energy are mainly used as hole injectors or hole transporters, and organic substances with relatively large electronegativity are mainly used as electron injectors or electron transporters. In addition, the substances used in the light-emitting auxiliary layer preferably satisfy the following characteristics.

[0003] First, the substances used in organic electroluminescent elements need to have good thermal stability. The reason is that Joule heat is generated due to the migration of charges inside the organic electroluminescent elements. Currently, the glass transition temperature of the material commonly used as the hole transport layer is low, so when driven at low temperatures, the phenomenon of reduced luminous efficiency due to crystallization occurs. Second, in order to reduce the driving voltage, the organic substances adjacent to the cathode and anode need to be designed with a small charge injection barrier and a high charge mobility. Third, there is always an energy barrier at the interface between the electrode and the organic layer and at the interface between organic layers, inevitably accumulating some charges, so substances with excellent electrochemical stability need to be used.

[0004] The light-emitting layer is composed of two substances, a main emitter and a dopant. The dopant needs to have a high quantum efficiency, and compared with the dopant, the main emitter needs to have a large energy gap and is prone to energy transfer to the dopant. Displays for televisions, mobile devices, etc. achieve full color according to the three primary colors of red, green, and blue. The light-emitting layers are respectively composed of a red main emitter / dopant, a green main emitter / dopant, and a blue main emitter / dopant. Currently, blue light materials still have problems of low luminous quantum efficiency and poor color purity. The main reasons for this situation are that blue light comes from the transition between energy levels with a relatively wide energy gap, and there are certain difficulties in molecular design for organic compounds with a wide bandgap. Secondly, there is a strong π-π bond interaction in the blue light material system, with strong charge transfer characteristics, so there are more non-radiative relaxation channels in the wide bandgap, exacerbating fluorescence quenching between molecules and reducing the quantum yield of the blue light system.

[0005] In view of the above reasons, the present invention is specifically proposed. Summary of the Invention

[0006] To solve the above problems existing in the prior art, the present invention provides an anthracene derivative containing boron atoms, an organic electroluminescent material, a light-emitting device, and a consumer product. The anthracene derivative of the present invention emits light in a blue to dark blue color and has a high luminous efficiency.

[0007] The first object of the present invention is to provide an anthracene derivative.

[0008] The second object of the present invention is to provide an organic electroluminescent material.

[0009] The third object of the present invention is to provide an organic electroluminescent device.

[0010] The fourth object of the present invention is to provide a consumer product.

[0011] To achieve the above objects, the present invention adopts the following technical solutions:

[0012] An anthracene derivative, the structural general formula of the anthracene derivative is shown in formula (I):

[0013]

[0014] Among them, two adjacent Ws represent groups shown in formula (II) or formula (III);

[0015]

[0016] Z is independently selected from CR 3 or N; G is selected from O, S, SO2, Se, CR 4 R 5 or NR 6 ; two adjacent "^" represent two adjacent Ws in formula (I);

[0017] X is selected from a single bond, O, S, S=O, SO2, Se, CR 4 R 5 、C=O、NR 6 、PR 6 、R 6 P=O、SiR 4 R 5 、GeR 4 R 5 、or BR 6 ;

[0018] R 1 、R 2 、R 3 、R 4 、R 5 、R 6 are independently selected from the group consisting of hydrogen, deuterium, halogen atoms, cyano groups, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C 30 heteroalkyl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C1-C 30 alkoxy, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C1-C 30 alkylthio, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 30 alkylamino, substituted or unsubstituted C6-C 60 arylamino, substituted or unsubstituted C1-C 30 alkylsilyl, substituted or unsubstituted C6-C 60 arylsilyl, substituted or unsubstituted C2-C 30 alkenyl, substituted or unsubstituted C2-C 30 alkynyl, or a group represented by formula (II);

[0019]

[0020] Ar 1 、Ar 2 each independently selected from the group consisting of substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 arylamino, substituted or unsubstituted C2-C 60 heteroaryl;

[0021] L is selected from the group consisting of a single bond, substituted or unsubstituted C6-C 60 arylene, substituted or unsubstituted C2-C 60 heteroarylene;

[0022] R 1 represents one or more up to saturated substitution;

[0023] *— represents the bonding position.

[0024] An aryl in the sense of the present invention contains 6 - 60 carbon atoms, and a heteroaryl in the sense of the present invention contains 2 - 60 carbon atoms and at least one heteroatom, provided that the sum of the carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O, or S. At this time, two or more rings of the heteroaryl can be simply attached to each other or attached in a condensed form, and further, it can also include a form condensed with an aryl. As non - limiting examples of the aryl and heteroaryl, they are especially selected from the following groups: phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthryl, pyrenyl, -yl, perylenyl, fluoranthenyl, tetraphenyl, pentaphenyl, benzopyrenyl, biphenyl, azobenzene, terphenyl, triphenylbenzene, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, triphenylene, dihydropyrenyl, tetrahydropyrenyl, cis - or trans - indenofluorene, cis - or trans - indolocarbazole, indolocarbazole, benzofurocarbazole, benzothienocarbazole, benzocarbazole, dibenzocarbazole, azadibenzo[g,Id]naphtho[2,1,8 - cde]azulene, trindene, isotrindene, spirotrindene, spiroisotrindene, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo[5,6]quinolinyl, benzo[6,7]quinolinyl, benzo[7,8]quinolinyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthrimidazolyl, pyridinimidazolyl, pyrazinimidazolyl, quinoxalinimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, isoxazolyl, 1,2 - thiazolyl, 1,3 - thiazolyl, benzothiazolyl, pyridazinyl, hexaazaphenanthryl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5 - diazaanthracenyl, 2,7 - diazapyrenyl, 2,3 - diazapyrenyl, 1,6 - diazapyrenyl, 1,8 - diazapyrenyl, 4,5 - diazapyrenyl, 4,5,9,10 - tetraazaperylenyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluorene ring group, naphthyridinyl, azacarbazolyl, benzocarbolinyl, carbolinyl, phenanthrolinyl, 1,2,3 - triazolyl, 1,2,4 - triazolyl, benzotriazolyl, 1,2,3 - oxadiazolyl, 1,2,4 - oxadiazolyl, 1,2,5 - oxadiazolyl, 1,3,4 - oxadiazolyl, 1,2,3 - thiadiazolyl, 1,2,4 - thiadiazolyl, 1,2,5 - thiadiazolyl, 1,3,4 - thiadiazolyl, 1,3,5 - triazinyl, 1,2,4 - triazinyl, 1,2,3 - triazinyl, tetrazolyl, 1,2,4,5 - tetrazinyl, 1,2,3,4 - tetrazinyl, 1,2,3,5 - tetrazinyl, purinyl, pteridinyl, indolizinyl, quinazolinyl, benzothiadiazolyl, and groups composed of the group or groups derived from combinations of these systems.

[0025] Further, the heteroaryl or heteroaromatic group is a group consisting of the groups shown in II-1 to II-17, and the specific structures of II-1 to II-17 are as follows:

[0026]

[0027]

[0028] Among them, Z1 and Z2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, nitrile, nitro, amino, amidino, hydrazino, hydrazono, carboxyl or its carboxylate, sulfonic acid group or its sulfonate, phosphoric acid group or its phosphate, C1-C 40 alkyl, C2-C 40 alkenyl, C2-C 40 alkynyl, C1-C 40 alkoxy, C3-C 40 cycloalkyl, C3-C 40 cycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthioether group, or substituted or unsubstituted C2-C 60 heteroaryl group;

[0029] x1 represents an integer from 1 to 4; x2 represents an integer from 1 to 3; x3 represents 1 or 2; x4 represents an integer from 1 to 6; x5 represents an integer from 1 to 5;

[0030] T1 represents an oxygen atom or a sulfur atom;

[0031] represents the connecting bond between the substituent and the main structure.

[0032] The alkyl used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a straight-chain or branched-chain saturated hydrocarbon having 1 to 40 carbon atoms. As non-limiting examples thereof, there are methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, etc. Heteroalkyl refers to that a hydrogen atom or -CH2- on the alkyl is substituted by at least one heteroatom selected from halogen, nitrile, N, O, S or silicon. As non-limiting examples, there are monofluoromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, pentafluoroethyl, nitrile, acetonitrile group, methoxymethyl, methoxyethyl, trimethylsilyl, triisopropylsilyl, etc.

[0033] The alkenyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a straight-chain or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Non-limiting examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, and the like.

[0034] The alkynyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a straight-chain or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Non-limiting examples thereof include ethynyl, 2-propynyl, and the like.

[0035] Generally, the cycloalkyl group and cycloalkenyl group according to the present invention refer to a monovalent functional group obtained by removing one hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, in which one or more -CH2- groups may be replaced by the above groups; in addition, one or more hydrogen atoms may also be replaced by deuterium atoms, halogen atoms or nitrile groups.

[0036] The heterocycloalkyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms. At this time, one or more carbons in the ring, preferably 1 to 3 carbons, are replaced by heteroatoms such as N, O or S. Non-limiting examples thereof include tetrahydrofuranyl, tetrahydrothienyl, morpholinyl, piperazinyl, pyranyl, tetrahydropyranyl, and the like.

[0037] The alkoxy group used in the present invention refers to RO - The monovalent functional group represented, wherein the above R is an alkyl group having 1 to 40 carbon atoms, which may include a straight-chain, branched or cyclic structure. Non-limiting examples of such alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, n-butoxy, pentyloxy, cyclopentyloxy, cyclohexyloxy, and the like.

[0038] The alkylthio group used in the present invention refers to R 0 S - The monovalent functional group represented, wherein the above R 0 is an alkyl group having 1 to 40 carbon atoms, which may include a straight-chain, branched or cyclic structure. Non-limiting examples of such alkylthio groups include methylthio, ethylthio, n-propylthio, isopropylthio, tert-butylthio, n-butylthio, and the like.

[0039] The aryloxy group used in the present invention refers to R'O - The monovalent functional group represented, wherein the above R' is an aryl group having 6 to 60 carbon atoms. Non-limiting examples of such aryloxy groups include phenoxy, naphthyloxy, biphenyloxy, and the like.

[0040] The arylthio group used in the present invention refers to R"S - The monovalent functional group represented by the above R" is an aryl group having 6 to 60 carbon atoms. Non-limiting examples of such arylthio groups include phenylthio group, naphthylthio group, biphenylthio group, etc.

[0041] "Halogen" or "halogen atom" used in the present invention refers to fluorine, chlorine, bromine or iodine selected from.

[0042] The alkylsilyl group used in the present invention refers to a silyl group substituted by an alkyl group having 1 to 30 carbon atoms, and the number of carbon atoms constituting the alkylsilyl group is at least 3. Non-limiting examples of the alkylsilyl group include trimethylsilyl group, triethylsilyl group, etc. The arylsilyl group refers to an alkylsilyl group substituted by at least one aryl group having 6 to 60 carbon atoms. Non-limiting examples include phenyldimethylsilyl group, naphthyldimethylsilyl group, phenyldiethylsilyl group, diphenylmethylsilyl group, diphenylethylsilyl group, triphenylsilyl group, etc.

[0043] The arylalkyl group of the present invention refers to an alkyl group in which at least one hydrogen atom of a straight-chain or branched-chain saturated hydrocarbon having 1 to 30 carbon atoms is substituted by an aryl group having 6 to 60 carbon atoms. Non-limiting examples may be phenylmethyl, diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, etc.

[0044] The alkylaryl group of the present invention refers to an aryl group in which at least one hydrogen atom of an aryl group having 6 to 60 carbon atoms is substituted by a straight-chain or branched-chain saturated hydrocarbon having 1 to 30 carbon atoms. Non-limiting examples may be methylphenyl, dimethylphenyl, trimethylphenyl, tert-butylphenyl, isopropylphenyl, etc.

[0045] The alkylamino group used in the present invention refers to an amino group substituted by an alkyl group having 1 to 40 carbon atoms, or a secondary amino group substituted by two alkyl groups having 1 to 40 carbon atoms. Non-limiting examples of the alkylamino group include methylamino group, dimethylamino group, ethylamino group, diethylamino group, etc.

[0046] The arylamino group used in the present invention refers to an amino group substituted by an aryl group having 6 to 60 carbon atoms, or a secondary amino group substituted by two aryl groups having 6 to 60 carbon atoms, or a secondary amino group substituted by one alkyl group having 1 to 40 carbon atoms and one aryl group having 6 to 60 carbon atoms. Non-limiting examples of the arylamino group include anilino group, diphenylamino group, 1-naphthylamino group, 2-naphthylamino group, N-phenylnaphthalen-1-ylamino group, carbazolyl group, phenoxazinyl group, etc.

[0047] In the present invention, in a substituted or unsubstituted ring formed by adjacent groups bonding to each other, "ring" refers to a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

[0048] In the present invention, a five-membered carbon ring refers to an alicyclic ring composed of five carbon atoms, such as cyclopentane, cyclopentene, benzindene, naphthindene, etc. A five-membered heterocyclic ring refers to a five-membered heteroaromatic ring containing at least two carbon atoms. As non-limiting examples, for instance, furan, thiophene, pyrrole, imidazole, benzofuran, benzothiophene, indole, etc. A six-membered carbon ring refers to a six-membered hydrocarbon ring or six-membered aromatic ring containing at least two carbon atoms. As non-limiting examples, for example, cyclohexane, cyclohexene, benzene, naphthalene, phenanthrene, etc. A six-membered heterocyclic ring refers to a six-membered heterocyclic ring or six-membered heteroaromatic ring containing at least two carbon atoms. As non-limiting examples, for example, pyran, piperidine, pyridine, piperazine, pyrazine, etc.

[0049] Further, each Z is independently selected from CR 3 。

[0050] Further, X is selected from O, S, S=O, SO2, NR 6 。

[0051] Further, G is selected from O, S, or NR 6 。

[0052] Further, the R 1 、R 2 、R 3 are each independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C 30 alkyl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C1-C 30 alkoxy, substituted or unsubstituted C6-C 60 arylamino, or formula (II).

[0053] Further, the Ar 1 、Ar 2 、R 6 are each independently selected from the group consisting of substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 arylamino, substituted or unsubstituted C2-C 60 heteroaryl.

[0054] According to an embodiment of the present invention, the R 1 ~R 5Each independently selected from the group consisting of hydrogen, deuterium, cyano, methyl, ethyl, isopropyl, isobutyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted group, substituted or unsubstituted perylenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl.

[0055] According to an embodiment of the present invention, the Ar 1 and Ar 2 and R 6 are each independently selected from the group consisting of substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthryl, pyrenyl, Groups consisting of a base, a perylene base, a fluoranthene base, a tetracenyl, a pentacenyl, a benzopyrene base, a biphenyl group, an o-phenylenediimine group, a terphenyl group, a triphenylphenyl group, a quaterphenyl group, a fluorenyl group, a spirobifluorenyl group, a dihydrophenanthrenyl group, a triphenylene group, a dihydropyrenyl group, a tetrahydropyrenyl group, a cis- or trans-indeno[1,2-b]fluorene group, a cis- or trans-indeno[2,1-b]carbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzocarbazole group, a dibenzocarbazole group, azadibenzo[g,1,2-de:4,5-d'e']naphtho[2,1,8-cde]azulene, a trindene group, an isotrindene group, a spirotrindene group, a spiroisotrindene group, a furyl group, a benzofuryl group, an isobenzofuryl group, a dibenzofuryl group, a thienyl group, a benzothienyl group, an isobenzothienyl group, a dibenzothienyl group, a pyrrolyl group, an indolyl group, an isoindolyl group, a carbazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, an acridinyl group, a phenanthridinyl group, a benzo[5,6]quinolinyl group, a benzo[6,7]quinolinyl group, a benzo[7,8]quinolinyl group, a phenothiazinyl group, a phenoxazinyl group, a pyrazolyl group, an indazolyl group, an imidazolyl group, a benzimidazolyl group, a naphthimidazolyl group, a phenanthrimidazolyl group, a pyridinimidazolyl group, a pyrazinimidazolyl group, a quinoxalinimidazolyl group, an oxazolyl group, a benzoxazolyl group, a naphthoxazolyl group, an anthroxazolyl group, a phenanthroxazolyl group, an isoxazolyl group, a 1,2-thiazolyl group, a 1,3-thiazolyl group, a benzothiazolyl group, a pyridazinyl group, a hexaazapentacene group, a benzopyridazinyl group, a pyrimidinyl group, a benzopyrimidinyl group, a quinoxalinyl group, a 1,5-diazaanthracenyl group, a 2,7-diazapyrenyl group, a 2,3-diazapyrenyl group, a 1,6-diazapyrenyl group, a 1,8-diazapyrenyl group, a 4,5-diazapyrenyl group, a 4,5,9,10-tetraazaperylene group, a pyrazinyl group, a phenazinyl group, a phenoxazinyl group, a phenothiazinyl group, a fluoranthene ring group, a naphthyridinyl group, an azacarbazolyl group, a benzocarbazolyl group, a carbazolyl group, a phenanthroline group, a 1,2,3-triazolyl group, a 1,2,4-triazolyl group, a benzotriazolyl group, a 1,2,3-oxadiazolyl group, a 1,2,4-oxadiazolyl group, a 1,2,5-oxadiazolyl group, a 1,3,4-oxadiazolyl group, a 1,2,3-thiadiazolyl group, a 1,2,4-thiadiazolyl group, a 1,2,5-thiadiazolyl group, a 1,3,4-thiadiazolyl group, a 1,3,5-triazinyl group, a 1,2,4-triazinyl group, a 1,2,3-triazinyl group, a tetrazolyl group, a 1,2,4,5-tetrazinyl group, a 1,2,3,4-tetrazinyl group, a 1,2,3,5-tetrazinyl group, a purinyl group, a pteridinyl group, an indolizinyl group, a quinazolinyl group, a benzothiadiazolyl group, or a group derived from a combination of these systems.

[0056] Further, L is selected from a single bond or a group consisting of the following groups represented by III-1 to III-23:

[0057]

[0058]

[0059] Among them, the dotted line represents the connection site of the group.

[0060] In the present invention, the substituted C6-C 60 aryl, substituted C6-C 60 aryloxy, substituted C6-C 60 arylthioether group, substituted C2-C 60 heteroaryl, etc., and the substituents are selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, nitrile, nitro, amino, amidino, hydrazino, hydrazone, carboxyl or its carboxylate, sulfonic acid group or its sulfonate, phosphoric acid group or its phosphate, C1-C 40 alkyl, C2-C 40 alkenyl, C2-C 40 alkynyl, C1-C 40 alkoxy, C3-C 40 cycloalkyl, C3-C 40 cycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthioether group, or C2-C 60 heteroaryl group.

[0061] As used herein, "a combination thereof" or "a group" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that can be envisioned by a person of ordinary skill in the art from the applicable list. For example, an alkyl group and deuterium can be combined to form a partially or fully deuterated alkyl group; a halogen and an alkyl group can be combined to form a haloalkyl substituent, such as trifluoromethyl, etc.; and a halogen, an alkyl group, and an aryl group can be combined to form a haloarylalkyl group.

[0062] Furthermore, the anthracene derivative is one of the following structures B751 to B879:

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070] Among them, the hydrogen atoms in the structure can be partially or completely replaced by deuterium atoms;

[0071] *—X—* is independently selected from *—O—*, *—S—*, *—S=O—*, *—SO2—* or one of the structures shown below:

[0072]

[0073] *—G—* is independently selected from *—O—*, *—S—*, *—S=O—*, *—SO2—* or one of the structures shown below:

[0074]

[0075] *—Q—* is independently selected from *—O—*, *—S—* or one of the structures shown below:

[0076]

[0077] *—And—* represents a connecting bond.

[0078] An organic electroluminescent material, wherein the organic electroluminescent material comprises the anthracene derivative containing a boron atom.

[0079] The organic electroluminescent material can be composed of the compound of the present invention alone, or can also contain other compounds simultaneously.

[0080] The compound of the present invention contained in the organic electroluminescent material of the present invention can be used as, but not limited to, a luminescent layer material.

[0081] An organic electroluminescent device, wherein the organic electroluminescent device comprises a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode, and the organic layer contains the anthracene derivative provided by the present invention.

[0082] The organic electroluminescent device comprises a cathode, an anode and at least one luminescent layer. In addition to these layers, it can also contain other layers, for example, in each case, containing one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers and / or charge generation layers. An intermediate layer having, for example, an exciton blocking function can also be introduced between two luminescent layers. However, it should be noted that each of these layers is not necessarily present. The organic electroluminescent device described herein can contain one luminescent layer, or it can contain multiple luminescent layers. A variety of luminescent compounds capable of emitting light are used in the luminescent layer. A system having three luminescent layers is preferred, wherein the three layers can exhibit blue, green and red luminescence. If there are more than one luminescent layer, then according to the present invention, at least one of these layers contains the compound of the present invention.

[0083] Furthermore, the organic electroluminescent device according to the present invention does not include a separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer, that is, the light-emitting layer is directly adjacent to the hole injection layer or the anode, and / or the light-emitting layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode.

[0084] In other layers of the organic electroluminescent device according to the present invention, especially in the hole injection and hole transport layers and in the electron injection and electron transport layers, all materials can be used in the manner commonly used according to the prior art. Those of ordinary skill in the art will thus be able to use in combination with the light-emitting layer according to the present invention all materials known for organic electroluminescent elements without creative effort.

[0085] Furthermore, a preferred organic electroluminescent device is one in which one or more layers are applied by a sublimation method, wherein the material is deposited by vapor deposition in a vacuum sublimation apparatus at an initial pressure below 10 -5 Pa, preferably below 10 -6 Pa. However, the initial pressure may even be lower, for example below 10 -7 Pa.

[0086] Also preferred is an organic electroluminescent device in which one or more layers are applied by an organic vapor deposition method or by carrier gas sublimation, wherein the material is deposited at a pressure between 10 -5 Pa and 1 Pa. A particular example of this method is the organic vapor jet printing method, in which the material is applied directly through a nozzle and is thus structured.

[0087] Furthermore, a preferred organic electroluminescent device is one in which one or more layers are produced from a solution, for example by spin coating, or by any desired printing method such as screen printing, flexographic printing, lithographic printing, photothermographic imaging, thermal transfer, inkjet printing or nozzle printing. Soluble compounds are obtained, for example, by appropriately substituted compounds of formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers. Also feasible are hybrid methods, in which, for example, one or more layers are applied from a solution and one or more additional layers are applied by vapor deposition.

[0088] These methods are generally known to those of ordinary skill in the art, and they can apply them to organic electroluminescent elements containing the compounds according to the present invention without creative effort.

[0089] Accordingly, the present invention also relates to a method for manufacturing an organic electroluminescent device according to the present invention, wherein at least one layer is applied by means of a sublimation method, and / or at least one layer is applied by means of an organic vapor deposition method or by means of carrier gas sublimation, and / or at least one layer is applied from a solution by spin coating or by means of a printing method.

[0090] In addition, the present invention relates to a compound comprising at least one compound of the present invention as indicated above. The same preferred cases as indicated above with respect to the organic electroluminescent device apply to the compound of the present invention. In particular, the compound may preferably further comprise other compounds. Processing the compound of the present invention from a liquid phase, for example by spin coating or by a printing method, requires a formulation for processing the compound of the present invention. These formulations can be, for example, solutions, dispersions or emulsions. For this purpose, a mixture of two or more solvents is preferably used. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, decalin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenyltoluenes, especially 3-phenyltoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decahydronaphthalene, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-methylcumene, phenetole, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, or a mixture of these solvents.

[0091] Furthermore, the organic layer is selected from one or more of an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer, and a light emitting layer.

[0092] Furthermore, the light emitting layer comprises an anthracene derivative of the present invention.

[0093] Furthermore, the light emitting layer includes a dopant and a light emitting host, and the host includes a group consisting of anthracene, naphthalene, anthracene, pyrene, perylene, phenanthrene, fluoranthene, benz[a]anthracene, fluorene, spirofluorene, and pentacene and their derivatives; the dopant comprises an anthracene derivative of the present invention.

[0094] Further, the mass ratio of the dopant to the light-emitting host is 1:99 to 50:50.

[0095] A consumer product made of the organic electroluminescent device described above, the consumer product including the organic electroluminescent device provided by the present invention.

[0096] The consumer product described in the present invention may be one of the following products: flat panel display, computer monitor, medical monitor, television, billboard, lamp for internal or external lighting and / or signaling, head-up display, fully transparent or partially transparent display, flexible display, laser printer, telephone, cellular phone, tablet computer, phablet, personal digital assistant (PDA), wearable device, laptop computer, digital camera, video camera, viewfinder, microdisplay with a diagonal less than 2 inches, 3-D display, virtual reality or augmented reality display, vehicle, video wall comprising a plurality of tiled-together displays, theater or stadium screen, light therapy device, and sign.

[0097] Unless otherwise specified, the raw materials used in the present invention can be obtained through commercial purchase. Any range described in the present invention includes the end values and any numerical value between the end values, as well as any sub-range constituted by any numerical value between the end values or the end values.

[0098] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0099] The anthracene derivative described in the present invention is a novel organic electroluminescent compound with a large planar conjugate structure formed by anthracene and a substituted boron atom. The large planar anthracene derivative realizes the separation of HOMO and LUMO through resonance effects between boron-nitrogen, boron-oxygen, boron-sulfur, etc., thereby realizing the thermally activated delayed fluorescence (TADF) effect and achieving a shorter emission wavelength compared with existing compounds; thus, the efficiency and lifespan of the organic electroluminescent device containing this compound are improved; in addition, this compound improves the solubility in solution to solve the productivity and cost problems of the processes of conventional blue light materials, and can be used in the preparation of the light-emitting layer not only in its evaporation process but also in its solution process in the original processes. Description of the Drawings

[0100] In order to more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the following will briefly introduce the drawings required for the description of the embodiments or the prior art. Obviously, the drawings in the following description are only some embodiments of the present invention. For those of ordinary skill in the art, without creative efforts, other drawings can be obtained based on these drawings.

[0101] Figure 1Schematic diagram showing an organic light-emitting device 100. The illustration is not necessarily drawn to scale. The device 100 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light-emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. The device 100 can be fabricated by sequentially depositing the described layers.

[0102] Figure 2 Schematic diagram showing an organic light-emitting device 200 having two light-emitting layers. The device includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first light-emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light-emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 can be prepared by sequentially depositing the described layers. Since the most common OLED devices have one light-emitting layer, while the device 200 has a first light-emitting layer and a second light-emitting layer, the emission peak shapes of the first light-emitting layer and the second light-emitting layer can be overlapping or cross-overlapping or non-overlapping. In the corresponding layers of the device 200, materials similar to those described with respect to the device 100 can be used. Figure 2 An example of how to add some layers to the structure of the device 100 is provided. Detailed Description

[0103] To make the objectives, technical solutions, and advantages of the present invention clearer, the technical solutions of the present invention will be described in detail below. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all of the embodiments. All other embodiments obtained by those of ordinary skill in the art based on the embodiments of the present invention without making creative efforts fall within the scope of the present invention.

[0104] In the present invention, the preparation methods are all conventional methods unless otherwise specified. The raw materials used can be obtained from public commercial channels unless otherwise specified, and the percentages are all mass percentages unless otherwise specified. A series of novel organic compounds provided by the present invention, all reactions are carried out under well-known suitable conditions, some involve simple organic preparations, such as the preparation of N,N-diphenylamine derivatives, which can all be synthesized through skilled operation skills and are not described in detail in the present invention.

[0105] The test instruments and methods for testing the performance of OLED materials and components in the following examples are as follows:

[0106] OLED component performance detection conditions:

[0107] Luminance and chromaticity coordinates: Measured using the spectral scanner PhotoResearch PR-715;

[0108] Current density and turn-on voltage: Measured using the digital source meter Keithley 2420;

[0109] Power efficiency: Measured using NEWPORT 1931-C;

[0110] Lifetime test: Conducted using the LTS-1004AC lifetime test device.

[0111] Example 1

[0112] A method for preparing compound B753, taking X = O and G = S as examples, includes the following steps:

[0113] The first step: Preparation of compound Int.-1

[0114]

[0115] Under nitrogen protection, 20.0 mmol of 10-(2-naphthyl)-9-bromoanthracene and 24.0 mmol of 3-fluoro-2-chlorophenylboronic acid were dissolved in 60 mL of toluene, 30 mL of ethanol, and 30 mL of water. Then, 50.0 mmol of anhydrous sodium carbonate, 0.2 mmol of Pd(PPh3)4, and 0.1 mmol of tetrabutylammonium bromide were added. The temperature was raised to reflux, and the mixture was stirred and reacted for 15 hours. After cooling to room temperature, 50 mL of water was added, and the mixture was extracted with ethyl acetate. The organic phase was collected, dried, filtered, and the filtrate was concentrated and dried under reduced pressure. It was separated and purified by silica gel column chromatography to obtain the intermediate Int.-1, a white solid, with a yield of 84%.

[0116] The second step: Preparation of compound Int.-2

[0117]

[0118] Under nitrogen protection, 20.0 mmol of Int.-1 prepared in the first step, 20.0 mmol of sub-3, and 40.0 mmol of anhydrous potassium carbonate were dispersed in 60 mL of N-methylpyrrolidone-2-one. The temperature was raised to 120 °C, and the mixture was stirred and reacted for 15 hours. After cooling to room temperature, 150 mL of water was added, and the mixture was extracted with dichloromethane. The organic phase was collected, washed with water, dried, filtered, and the filtrate was concentrated and dried under reduced pressure. It was separated and purified by silica gel column chromatography to obtain Int.-2, with a yield of 62%.

[0119] The third step: Preparation of compound B753

[0120]

[0121] Under nitrogen protection, 10.0 mmol of the intermediate Int.-2 prepared in the second step was dissolved in 120 mL of dry xylene, cooled to -30 °C, 4.8 mL of 2.5 M n-butyllithium n-hexane solution was added dropwise, the temperature was raised to 50 °C and stirred for 1 hour, then cooled to -30 °C again, 12.0 mmol of boron tribromide was added dropwise, the temperature was raised to room temperature and stirred for 1 hour, cooled to 0 °C, 20.0 mmol of N,N-diisopropylethylamine was added dropwise, the temperature was raised to 125 °C and stirred for 24 hours, concentrated under reduced pressure and dried, and purified by silica gel column chromatography to obtain compound B751;

[0122] X = O, G = S, yellow solid, yield 37%, HRMS(ESI) m / z theoretical value: 536.14; experimental value: 536.14 [M + .

[0123] X = S, G = S, yellow solid, yield 34%, HRMS(ESI) m / z theoretical value: 552.11; experimental value: 552.12 [M + .

[0124] Example 2

[0125] The preparation method of compound B778, taking X = 4-tert-butylphenyl as an example, includes the following steps:

[0126] The first step: Preparation of compound Int.-3

[0127]

[0128] Under nitrogen protection, 24.0 mmol of 9-bromoanthracene, 20.0 mmol of sub-5 and 30.0 mmol of sodium tert-butoxide were dispersed in 80 mL of toluene, 0.1 mmol of Pd2(dba)3CHCl3 and 0.2 mmol of Xantphos were added, the temperature was raised to 100 °C and stirred for 15 hours, cooled to room temperature, 50 mL of water was added, the organic phase was separated, the aqueous phase was extracted with dichloromethane, the organic phase was collected, dried, filtered, the filtrate was concentrated under reduced pressure and dried, and purified by silica gel column chromatography to obtain Int.-3, yellow solid, yield 74%.

[0129] The second step: Preparation of compound Int.-4

[0130]

[0131] Under nitrogen protection, 20.0 mmol of Int.-3 and 2.0 mmol of p-toluenesulfonic acid were dissolved in 60 mL of dichloromethane. The temperature was lowered to 0 °C, and 22.0 mmol of NBS was added in portions. The mixture was stirred for 2 hours, 50 mL of water was added, and the organic phase was separated. The aqueous phase was extracted with dichloromethane, the organic phases were collected, dried, filtered, and the filtrate was concentrated and dried under reduced pressure. It was separated and purified by silica gel column chromatography to obtain Int.-4, a yellow solid, with a yield of 95%.

[0132] Step 3: Preparation of compound Int.-5

[0133]

[0134] Referring to the synthesis method of the first step of Example 1, 10-(2-naphthyl)-9-bromoanthracene in the first step of Example 1 was replaced with Int.-4, and 3-fluoro-2-chlorophenylboronic acid in the first step of Example 1 was replaced with sub-6. It was separated and purified by silica gel column chromatography to obtain Int.-5, a yellow solid, with a yield of 74%.

[0135] Step 4: Preparation of compound Int.-6

[0136]

[0137] Under nitrogen protection, 12.0 mmol of Int.-5, 10.0 mmol of sub-7 and 15.0 mmol of sodium tert-butoxide were dispersed in 80 mL of toluene. Then 0.1 mmol of Pd2(dba)3 and 0.2 mmol of Xantphos were added. The temperature was raised to 100 °C and the mixture was stirred for 15 hours. It was cooled to room temperature, 50 mL of water was added, and the organic phase was separated. The aqueous phase was extracted with dichloromethane, the organic phases were collected, dried, filtered, and the filtrate was concentrated and dried under reduced pressure. It was separated and purified by silica gel column chromatography to obtain Int.-6, a yellow solid, with a yield of 82%.

[0138] Step 2: Preparation of compound B778

[0139]

[0140] Referring to the synthesis method of the third step of Example 1, only Int.-2 in the third step of Example 1 was replaced with Int.-6. It was separated and purified by silica gel column chromatography to obtain compound B778;

[0141] G = O, a yellow solid, with a yield of 33%, HRMS (ESI) m / z theoretical value: 804.42; experimental value: 805.43 [M + H];

[0142] G = S, a yellow solid, with a yield of 35%, HRMS (ESI) m / z theoretical value: 820.40; experimental value: 821.40 [M + H];

[0143] Example 3

[0144] The preparation method of compound B824, taking Q = CMe2 as an example, comprises the following steps:

[0145] The first step: Preparation of compound Int.-7

[0146]

[0147] Under nitrogen protection, 20.0 mmol of Int.-5’ (prepared by referring to the synthesis method of Example 2), 20.0 mmol of sub-8 and 40.0 mmol of anhydrous potassium carbonate are dispersed in 60 mL of N-methylpyrrolidin-2-one, heated to 120 °C, stirred and reacted for 15 hours, cooled to room temperature, 150 mL of water is added, extracted with dichloromethane, the organic phase is collected, washed with water, dried, filtered, the filtrate is concentrated and dried under reduced pressure, and purified by silica gel column chromatography to obtain Int.-7 with a yield of 73%.

[0148] The second step: Preparation of compound B824

[0149]

[0150] Under nitrogen protection, 10.0 mmol of intermediate Int.-7 is dissolved in 120 mL of dry tert-butylbenzene, cooled to -78 °C, 6.0 mL of 2.5 M n-butyllithium hexane solution is added dropwise, heated to 50 °C and stirred and reacted for 1 hour, cooled to -78 °C again, 12.0 mmol of boron tribromide is added dropwise, warmed to room temperature, stirred and reacted for 1 hour, cooled to 0 °C, 20.0 mmol of N,N-diisopropylethylamine is added dropwise, heated to 125 °C and stirred and reacted for 24 hours, concentrated and dried under reduced pressure, and purified by silica gel column chromatography to obtain compound B824;

[0151] X = O, G = O, yellow solid, yield 36%, HRMS (ESI) m / z theoretical value: 677.25; experimental value: 678.25 [M+H].

[0152] X = S, G = O, yellow solid, yield 35%, HRMS (ESI) m / z theoretical value: 693.22; experimental value: 694.23 [M+H].

[0153] X = NtBuPh, yellow solid, yield 28%, HRMS (ESI) m / z theoretical value: 808.36; experimental value: 809.37 [M+H].

[0154] Example 4

[0155] The preparation method of compound B832, comprises the following steps:

[0156] Step 1: Preparation of Compound Int.-8

[0157]

[0158] Referring to the synthesis method in the first step of Example 1, replace 10-(2-naphthyl)-9-bromoanthracene in the first step of Example 1 with sub-8, and replace 3-fluoro-2-chlorophenylboronic acid with sub-9 to prepare Compound Int.-8 with a yield of 70% - 75%.

[0159] Step 2: Preparation of Compound B832

[0160]

[0161] Under nitrogen protection, take 10.0 mmol of the intermediate Int.-8 prepared in the second step and dissolve it in 120 mL of dry xylene. Cool the temperature to -78 °C, and dropwise add 30.0 mmol of 1.5 M tert-butyllithium pentane solution. Warm up to 50 °C and stir for 1 hour. Cool the temperature to -78 °C again, and dropwise add 25.0 mmol of boron tribromide. Raise the temperature to room temperature and stir for 1 hour. Cool the temperature to 0 °C, and dropwise add 0.1 mol of N,N-diisopropylethylamine. Warm up to 125 °C and stir for 24 hours. Cool to room temperature, filter, wash the filter cake with toluene, and purify the solid by silica gel column chromatography to obtain Compound B832;

[0162] X = O, G = O, yellow solid, yield 27%, HRMS(ESI) m / z theoretical value: 686.18; experimental value: 686.19.

[0163] X = O, G = S, yellow solid, yield 30%, HRMS(ESI) m / z theoretical value: 718.14; experimental value: 718.14.

[0164] Example 5

[0165] The preparation method of Compound B874 includes the following steps:

[0166] Step 1: Preparation of Compound Int.-9

[0167]

[0168] Under nitrogen protection, 20.0 mmol of sub-10 (prepared according to the synthesis method of Reference Example 1) was dissolved in 120 mL of dry dichloromethane. The temperature was lowered to -10 °C, and 21.0 mmol of NBS was added in batches. The mixture was stirred and reacted for 5 hours. Then 50 mL of water was added, and the organic phase was separated. The organic phase was washed with water, dried, filtered, and the filtrate was concentrated to dryness under reduced pressure. It was separated and purified by silica gel column chromatography to obtain compound Int.-9 with a yield of 80% - 85%.

[0169] Step 2: Preparation of compound Int-10

[0170]

[0171] Under nitrogen protection, 20.0 mmol of Int.-9 and 24.0 mmol of triisopropyl borate were dissolved in 60 mL of dry THF. The temperature was lowered to -80 °C, and 24.0 mmol of 2.5 M n-butyllithium in n-hexane solution was added dropwise. The mixture was stirred and reacted for 1 hour, then warmed to room temperature. 100 mL of 1 M dilute hydrochloric acid aqueous solution was added, and the organic phase was separated. The aqueous phase was extracted with dichloromethane. The organic phase was washed with saturated brine, dried, filtered, and the filtrate was concentrated to dryness under reduced pressure. It was separated and purified by silica gel column chromatography to obtain compound Int.-10 as a white solid with a yield of 60% - 65%.

[0172] Step 3: Preparation of compound Int.-11

[0173]

[0174] 20.0 mmol of intermediate Int.-10 was dispersed in 100 mL of dry toluene. 40.0 mmol of o-phenylenediamine, 22.0 mmol of p-toluenesulfonic acid, and 2.0 mmol of anhydrous magnesium sulfate were added. The temperature was raised to reflux and stirred for 24 hours, then cooled to room temperature. The mixture was filtered, the filter cake was washed with toluene, and the filtrate was concentrated to dryness under reduced pressure. It was separated and purified by silica gel column chromatography to obtain compound Int.-11 as a yellow solid with a yield of 60% - 65%.

[0175] Step 4: Preparation of compound B874

[0176]

[0177] Under nitrogen protection, 10.0 mmol of intermediate Int.-11 was dispersed in 50 mL of dry o-dichlorobenzene. 25.0 mmol of boron tribromide was added, and the temperature was raised to reflux and stirred for 24 hours. Then it was cooled to room temperature, and 75.0 mmol of 1 M phenylmagnesium bromide in THF solution was added. The mixture was stirred at room temperature for 6 hours. 50 mL of water was added, and the organic phase was separated. The aqueous phase was extracted with dichloromethane, and the organic phase was collected, dried, filtered, and the filtrate was concentrated to dryness under reduced pressure. It was separated and purified by silica gel column chromatography to obtain compound B874;

[0178] X = O, G = S, yellow solid, yield 28%, HRMS(ESI) m / z theoretical value: 698.21; experimental value: 699.21 [M+H].

[0179] X = O, G = O, yellow solid, yield 25%, HRMS(ESI) m / z theoretical value: 682.23; experimental value: 683.24 [M+H].

[0180] X = NtBuPh, G = S, yellow solid, yield 29%, HRMS(ESI) m / z theoretical value: 829.32; experimental value: 830.32 [M+H].

[0181] Examples 6 - 128

[0182] Referring to the similar synthesis methods of the above Examples 1 - 5, the following compounds were prepared:

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199] In the above embodiments, *—X—* is independently selected from *—O—*, *—S—*, or one of the structures shown below:

[0200]

[0201] *—G—* is independently selected from *—O—*, *—S—*, *—S=O—*, *—SO2—*, or one of the structures shown below:

[0202]

[0203] *—Q—* is independently selected from *—O—*, *—S—*, or one of the structures shown below:

[0204]

[0205] Application Examples 1 to 129

[0206] An OLED device 100, as Figure 1 shown, the OLED device of this embodiment is a top-emitting light device, including a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light-emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. For the device that omits the hole blocking layer 107 of the OLED device, the preparation method includes the following steps:

[0207] 1) Ultrasonically treat the glass substrate coated with the ITO conductive layer in a cleaning agent for 30 minutes, rinse it in deionized water, ultrasonically treat it in an acetone / ethanol mixed solvent for 30 minutes, bake it in a clean environment until completely dry, irradiate it with an ultraviolet light cleaning machine for 10 minutes, and bombard the surface with a low-energy cation beam.

[0208] 2) Place the above-treated ITO glass substrate in a vacuum chamber, evacuate it to less than 1×10 -5 Pa, evaporate silver on the above ITO film as the anode 102, and the evaporation film thickness is Continue to evaporate the compounds DNTPD and F4TCNQ as the hole injection layer 103 respectively, where F4TCNQ is 3% of the mass of DNTPD, and the evaporation film thickness is Continue to evaporate NPD on the above hole injection layer film as the hole transport layer 104, and the evaporation film thickness is

[0209] 3) Continue to evaporate a layer of the compound HT202 on the hole transport layer as the electron blocking layer 105, and the evaporation film thickness is

[0210] 4) Continue to deposit a layer of the anthracene derivative represented by formula (I) of the present invention and BH017 on the electron blocking layer as the organic light-emitting layer 106, wherein BH017 is the host material and the anthracene derivative represented by formula (I) of the present invention is the doping material, and the doping concentration of the anthracene derivative represented by formula (I) in BH017 is 5%, and the deposited film thickness is

[0211] 5) Then continue to deposit a layer of compound LiQ and ET105 on the above light-emitting layer as the electron transport layer 108 of the device, wherein the mass ratio of LiQ and ET105 is 1:1, and the deposited film thickness is

[0212] 6) Then continue to deposit a layer of compound LiF on the above electron transport layer as the electron injection layer 109 of the device, and the deposited film thickness is

[0213] 7) Deposit metal magnesium and silver on the above electron injection layer as the transparent cathode 110 of the component, wherein the mass ratio of magnesium and silver is 2:1, and the deposited film thickness is

[0214] Finally, deposit a layer of compound NPD on the transparent cathode as the capping layer 111, and the deposited film thickness is

[0215] The structures of the compounds used in the above examples are as follows:

[0216]

[0217] Application Example 130

[0218] An organic electroluminescent element 200, which is a top-emitting multi-light-emitting layer element, and its structure is as Figure 2 shown. The device includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first light-emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light-emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The element can be prepared by sequentially depositing the described layers.

[0219] Because the most common organic electroluminescent devices have a single-color light-emitting layer or have three light-emitting layers of the three primary colors, and Figure 2 the element shown has two light-emitting layers of the same light color, and the light-emitting peak shapes of the first light-emitting layer and the second light-emitting layer of the element can be overlapping or cross-overlapping or non-overlapping. In the corresponding layers of the element shown, materials similar to those described for the element shown in Figure 2 can be used. Figure 1 the element shown.Figure 2 Provide an example of how to add some layers to the structure in the components shown in Figure 1 The specific preparation method is the same as that of the OLED component shown in Figure 1 the OLED component shown in Figure 1 and Figure 2 The simple layered structure described in Figure 2 is provided as a non-limiting example, and it should be understood that the embodiments of the present invention can be used in combination with a variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures can be used. Functional OLEDs can be achieved by combining the described individual layers in different ways based on design, performance, and cost factors, or several layers can be completely omitted. Other layers that are not specifically described can also be included. Materials different from those specifically described can be used. Although many of the examples provided herein describe various layers as including a single material, it will be understood that combinations of materials can be used, such as a mixture of a matrix and a dopant, or more generally, a mixture. Also, the layers can have various sub-layers. The names given to the individual layers herein are not intended to be strictly restrictive. For example, in the component shown in Figure 1 and Figure 2 the hole transport layer 204 transports holes and injects holes into the first light-emitting layer 205, and can be described as a hole transport layer or an electron blocking layer. In some embodiments, the OLED can be described as having an organic layer disposed between the cathode and the anode. This organic layer can include a single layer or can further include multiple layers of different organic materials as described in

[0220] The specific preparation method is the same as that of the OLED component described in Application Example 1 above.

[0221] Comparative Example 1

[0222] Referring to the same steps as in Application Example 1, except that Compound B1 is used instead of the anthracene derivative shown in Formula (I), Comparative Element 1 is prepared. The structure of Compound B1 is:

[0223]

[0224] The following performance tests are performed on the organic electroluminescent devices prepared by the above process:

[0225] The driving voltage, current efficiency, and lifetime of the organic electroluminescent devices prepared in Application Examples 1 to 130 and Comparative Example 1 are measured using a digital source meter and a luminance meter. Specifically, the voltage is increased at a rate of 0.1 V per second, and the voltage when the current density of the organic electroluminescent device reaches 10 mA / cm 2 is measured as the driving voltage, and the luminance at this time is also measured; the ratio of the luminance to the current density is the current efficiency; the LT95% lifetime test is as follows: Using a luminance meter at 1000 cd / m2 At a constant current under a certain brightness, measure the time when the brightness attenuation of the organic electroluminescent element reaches 950 cd / m 2 , and the unit is hours. The data listed in Table 2 are relative data compared with Comparative Element 1.

[0226] Table 2

[0227]

[0228]

[0229]

[0230]

[0231] In the above, Ph is phenyl, tBuPh is 4-tert-butylphenyl, Me is methyl, and FR is 9,9-fluorenyl;

[0232] As can be seen from Table 2, the anthracene derivative of the present invention as a blue light doping material obtains a deep blue light organic electroluminescent element. Compared with the organic electroluminescent element using B1 as the blue light doping material, it has a higher current efficiency, a lower driving voltage, and the initial brightness of the device is 1000 cd / m 2 . Under the starting conditions, the LT95% life of the device has also been greatly improved.

[0233] Compared with Compound B1 of Comparative Example 1, the main difference feature of the anthracene derivative of the present invention is that the boron-containing anthracene plane of B1 does not achieve the separation of HOMO and LUMO, while the anthracene derivative of the present invention separates HOMO and LUMO by using the conjugation effect of boron-nitrogen, boron-oxygen, etc., realizing the TADF effect. Therefore, the luminous efficiency is improved and excellent luminous performance is shown.

[0234] The organic electroluminescent device of the present invention can be applied in planar light-emitting bodies such as wall-mounted TVs, flat panel displays, lighting, backlights of copiers, printers, liquid crystal displays, or light sources of measuring instruments, display panels, indicator lights, etc.

[0235] The above is only the specific implementation manner of the present invention, but the protection scope of the present invention is not limited thereto. Any person skilled in the art within the technical scope disclosed by the present invention can easily think of changes or substitutions, which should be covered by the protection scope of the present invention. Therefore, the protection scope of the present invention should be subject to the protection scope of the claims.

Claims

1. An anthracene derivative, characterized in that, The general structural formula of the anthracene derivative is shown in Formula (I): Formula (I); Among them, two adjacent Ws represent the groups shown in Formula (II) or Formula (III); Formula (II), Formula (III); Z is independently selected from CR 3 ; G is selected from O, S or NR 6 ; two adjacent "^" represent two adjacent Ws in formula (I); X is selected from O or NR 6 ; R 1 、R 3 is hydrogen; R 2 each independently selected from the group consisting of hydrogen, deuterium, cyano, methyl, ethyl, isopropyl, isobutyl, tert-butyl, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, triphenylene, anthracenyl, benzanthracenyl, pyrenyl, chrysenyl, perylenyl, fluoranthenyl, carbazolyl, fluorenyl, indolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl or the group represented by formula (II); Formula (II); L is selected from the group consisting of a single bond, a phenylene group or a naphthylene group; Ar 1 、Ar 2 、R 6 each independently selected from the group consisting of substituted or unsubstituted phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, pyrenyl, chrysenyl, perylenyl, fluoranthenyl, tetraphenyl, pentaphenyl, benzopyrenyl, biphenyl, azobenzene, terphenyl, triphenyl, tetraphenyl, fluorene, spirobifluorene, dihydrophenanthrene, triphenylene, dihydropyrene, tetrahydropyrene, cis- or trans-indeno[1,2-b]fluorene, cis- or trans-indeno[2,1-b]carbazole, indolocarbazole, benzofurocarbazole, benzothienocarbazole, benzocarbazole, dibenzocarbazole, azadibenzo[g,id]naphtho[2,1,8-cde]azulene, trindene, isotrindene, spirotrindene, spiroisotrindene, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo[5,6]quinolinyl, benzo[6,7]quinolinyl, benzo[7,8]quinolinyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthrimidazolyl, pyridinimidazolyl, pyrazinimidazolyl, quinoxalinimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, isoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazaphenanthryl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthracenyl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluoranthenylene, naphthyridinyl, azacarbazolyl, benzocarboline, carboline, phenanthroline, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, quinazolinyl or benzothiadiazolyl; *— represents the bonding position.

2. An anthracene derivative, characterized in that, The anthracene derivative is one of the following structures: Wherein, *—X—* are each independently selected from *—O—* or one of the structures shown below: ; *—G—* is independently selected from *—O—*, *—S—* or one of the following structures: ; *—Q—* independently selects from *—O—*, *—S—* or one of the following structures respectively: 、 、 、 ； *— and —* represent connecting bonds.

3. An organic electroluminescent material, characterized in that, The organic electroluminescent material includes the anthracene derivative described in any one of Claims 1-2.

4. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode, and the organic layer contains the anthracene derivative described in any one of Claims 1-2.

5. The organic electroluminescent device according to claim 4, characterized in that, The organic layer is selected from one or more of an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer and a light emitting layer; the light emitting layer contains the anthracene derivative described in any one of Claims 1-2.

6. The organic electroluminescent device according to claim 5, characterized in that, The light emitting layer includes a dopant and a light emitting host, and the dopant contains the anthracene derivative described in any one of Claims 1-2.

7. The organic electroluminescent device according to claim 6, characterized in that, The mass ratio of the dopant to the light emitting host is 1:99 to 50:

50.

8. A consumer product, characterized in that, An organic electroluminescent device including any one of Claims 4-7.

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