Deuterated oxazole ring organic compound and application thereof

Abstract

The invention relates to the technical field of display, in particular to a deuterated oxazole ring organic compound and application thereof. The deuterated oxazole ring organic compound provided by the invention has the following general formula structure: # imgabs0 # is based on the structure of a formula (1), and deuterium atoms are introduced into the compound as shown in the formula (1), so that the stability of the organic compound can be effectively improved, and the service life of a device is further prolonged; the position of the deuteration is further limited, so that the HOMO and LUMO energy levels of the organic compound are well matched with adjacent energy levels, the carrier mobility is well balanced, and the device has the advantages of low voltage and high efficiency while having long service life; in conclusion, the deuterated oxazole ring organic compound provided by the invention has excellent properties, so that the prepared organic light-emitting device has the characteristics of low driving voltage, high light-emitting efficiency and long service life.

Description

Technical Field

[0001] The present invention relates to the field of display technology, and in particular to a deuterated oxazole ring organic compound and application thereof. Background Art

[0002] An organic electroluminescent device (OLED) is a device that changes electrical energy into light by applying electricity to an organic electroluminescent material, and generally has a structure comprising an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer of the organic EL device can be composed of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (which comprises a host material and a doping material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., and the materials used for the organic layer are classified into hole injection materials, hole transport materials, electron blocking materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, electron injection materials, etc. by their functions. In the organic EL device, due to the application of voltage, holes are injected from the anode into the light-emitting layer, electrons are injected from the cathode into the light-emitting layer, and high-energy excitons are formed by the recombination of holes and electrons. Through this energy, the organic light-emitting compound reaches an excited state, and luminescence is generated by emitting light due to the energy generated by the excited state of the organic light-emitting compound returning to the ground state.

[0003] The most important factor that determines the luminous efficiency in an organic EL device is the luminescent material. The luminescent material must have high quantum efficiency, high electron and hole mobility, and the luminescent material layer formed must be uniform and stable. The luminescent material is divided into blue luminescent material, green luminescent material, and red luminescent material according to the color of the luminescent light, and additionally yellow luminescent material or orange luminescent material. In addition, the luminescent material can also be divided into a host material and a doping material according to its function.

[0004] However, the existing organic electroluminescent materials have low stability, and the HOMO and LUMO energy levels have poor matching with adjacent energy levels, which leads to the problem of unbalanced carrier mobility, which in turn causes the organic electroluminescent devices containing the organic electroluminescent materials to have high driving voltage, low luminous efficiency and short life, which seriously limits the application of organic electroluminescent devices. Summary of the invention

[0005] The purpose of the present invention is to overcome the problems of low stability of existing organic electroluminescent materials, poor matching between HOMO and LUMO energy levels and adjacent energy levels, resulting in unbalanced carrier mobility, causing an organic electroluminescent device containing the organic electroluminescent material to have a high driving voltage, low luminous efficiency and short life, and further provide a deuterated oxazole ring organic compound and its application.

[0006] Definitions of substituent terms in this invention:

[0007] The term "organic electroluminescent material" in the present disclosure means a material that can be used in an organic electroluminescent device and can contain at least one compound. If necessary, the organic electroluminescent material can be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a luminescence auxiliary material, an electron blocking material, a luminescent material (containing a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0008] The term "multiple organic electroluminescent materials" in the present disclosure means one or more organic electroluminescent materials comprising a combination of at least two compounds, which may be included in any layer constituting an organic electroluminescent device. It may mean both a material contained in an organic electroluminescent device before (e.g., before vapor deposition) and a material contained in an organic electroluminescent device after (e.g., after vapor deposition). For example, a plurality of organic electroluminescent materials may be a combination of at least two compounds, which may be included in at least one of the following: a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescent auxiliary layer, a luminescent auxiliary layer, a luminescent layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. At least two compounds may be included in the same layer or in different layers, and may be mixed-evaporated or co-evaporated, or may be evaporated individually.

[0009] In the present application, the description methods used "each... is independently selected from" and "... are independently" and "... are independently" can be interchanged, and should be understood in a broad sense. It can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or it can mean that in the same group, the specific options expressed by the same symbols do not affect each other.

[0010] In this application, the term "substituent" has its ordinary meaning as known in the art and refers to a chemical moiety that is covalently attached to or, where appropriate, fused to a parent core group.

[0011] In the present application, the term "substituted or unsubstituted" means that the functional group recorded after the term may or may not have a substituent (hereinafter, for ease of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl or non-substituted aryl having a substituent Rc. Wherein the above-mentioned substituent, i.e., Rc, can be, for example, deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C1-C60 heteroaryl, and optionally, for example, deuterium, halogen group, cyano, alkyl, haloalkyl, trialkylsilyl, deuterated alkyl, aryl, heteroaryl, etc. Of course, the number of substituents Rc can be one or more. When two substituents Rc are connected to the same atom, the two substituents Rc can exist independently or be connected to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the adjacent substituents Rc can exist independently or be fused to form a ring with the functional group to which they are connected.

[0012] In the present application, the term "alkyl" refers to a saturated hydrocarbon group, whether used as part of other terms or alone, which can be straight or branched. The term "C1-C60 alkyl" is derived from a monovalent substituent of a straight or branched saturated hydrocarbon having 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and more preferably 1 to 20 carbon atoms, of course, examples thereof include but are not limited to methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl.

[0013] In the present application, the terms "aryl" and "arylene" include monocyclic, polycyclic or condensed-ring aromatic groups, the rings may be interrupted by short non-aromatic units, and may contain spiro structures. Aryl groups include but are not limited to phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, fluorenyl, spirobifluorenyl, etc., and arylene groups include but are not limited to phenylene, biphenylene, terphenylene, naphthyl, phenanthryl, anthracenyl, fluorenyl, spirobifluorenyl, etc.

[0014] In the present application, the term "heteroaryl" includes monocyclic, polycyclic or condensed-ring heteroaryl groups, and the rings may be interrupted by short non-aromatic units. The heteroatoms include nitrogen, oxygen, and sulfur. It can be understood that the heteroaryl groups include nitrogen-containing heteroaryl groups, oxygen-containing heteroaryl groups, sulfur-containing heteroaryl groups, nitrogen-only heteroaryl groups, oxygen-only heteroaryl groups, and sulfur-only heteroaryl groups. Specifically, the heteroaryl groups in the present application include, but are not limited to, furanyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, thiazolyl, thiadiazole, thiazolyl ... yl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, Phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and derivatives thereof; heteroarylene groups include, but are not limited to, furanyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiazolyl, The term "substituted" refers to a substituted phenyl group, an isobenzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, an imidazolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoisoxazolyl group, a benzoxazolyl group, an isoindolyl group, an indolyl group, an indazolyl group, a benzothiadiazolyl group, a quinolyl group, an isoquinolyl group, a cinnolinyl group, a quinazolinyl group, a quinoxalinyl group, a carbazolyl group, a phenoxazinyl group, a phenothiazinyl group, a phenanthridinyl group, a benzodioxolyl group, a dihydroacridinyl group, and derivatives thereof. As used in the present invention, the term "substituted" refers to a hydrogen atom in a compound that is replaced by another substituent. The position is not limited to a specific position, as long as the hydrogen at the position can be replaced by a substituent. When two or more substituents are present, the two or more substituents may be the same or different.

[0015] As used herein, the term "halogen" refers to an atom selected from fluorine, chlorine, bromine and iodine.

[0016] In the present application, unless otherwise specified, a hydrogen atom includes protium, deuterium and tritium.

[0017] In the present application, the range of carbon atom number is defined in the definition of the group, and the carbon atom number is any integer within the defined range. For example, C6-C60 aromatic group, the carbon atom number representing the aromatic group can be any integer within the range of 6-60, for example 6, 8, 10, 13, 15, 17, 20, 22, 25, 30, 35, 40, 45, 50, 55 or 60, etc.

[0018] In the present application, unless otherwise specified, a substituent is not fused to the group in which it is located.

[0019] In the present application, if a group is not limited to being substituted or unsubstituted, it means being unsubstituted.

[0020] The present invention provides a deuterated oxazole ring organic compound, wherein the organic compound has a structure shown in formula (1):

[0021]

[0022] In the formula (1), ring A may be present or absent, and when present, ring A is selected from a benzene ring, a naphthalene ring, a benzofuran ring or a benzothiophene ring;

[0023] Ar is selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 arylamine group, a substituted or unsubstituted C3-C60 heteroarylamine group, or a substituted or unsubstituted C3-C60 heteroaryl group;

[0024] L is selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group;

[0025] R1 and R2 are deuterium;

[0026] R3 is selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 arylamine group, a substituted or unsubstituted C3-C60 heteroarylamine group, a substituted or unsubstituted C3-C60 heteroaryl group, and / or is bonded to an adjacent group to form a ring;

[0027] n1 is an integer selected from 0-12;

[0028] n2 is an integer selected from 0-3;

[0029] n3 is an integer selected from 0-5;

[0030] The substituents in the substituted C6-C60 aryl, substituted C6-C60 arylamine, substituted C3-C60 heteroarylamine, substituted C3-C60 heteroaryl, substituted C6-C60 arylene, and substituted C3-C60 heteroarylene are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0031] Wherein, formula (1) satisfies at least one of the following:

[0032] n1+n2≥1;

[0033] The deuteration rate of Ar is greater than 0;

[0034] The deuteration rate of L is greater than 0.

[0035] Understandably, Ring A and ring B are fused and connected.

[0036] It can be understood that formula (1) satisfies at least one of n1+n2≥1, the deuteration rate of Ar is greater than 0 or the deuteration rate of L is greater than 0. Specifically, n1+n2≥1 indicates that at least one of R1 and R2 exists; the deuteration rate of Ar is greater than 0, indicating that at least one of the hydrogens in Ar is replaced by deuterium; the deuteration rate of L is greater than 0, indicating that at least one of the hydrogens in L is replaced by deuterium.

[0037] Preferably, Ar is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C3-C30 heteroarylamine, substituted or unsubstituted C3-C30 heteroaryl;

[0038] Wherein, the substituents in the substituted C6-C30 aryl, substituted C6-C30 arylamine, substituted C3-C30 heteroarylamine, and substituted C3-C30 heteroaryl are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0039] Preferably, Ar is selected from substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C6-C25 arylamine, substituted or unsubstituted C3-C25 heteroarylamine, substituted or unsubstituted C3-C25 heteroaryl;

[0040] Wherein, the substituents in the substituted C6-C25 aryl, substituted C6-C25 arylamine, substituted C3-C25 heteroarylamine, and substituted C3-C25 heteroaryl are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0041] Preferably, the substituents in the substituted C6-C25 aryl group, the substituted C6-C25 arylamine group, the substituted C3-C25 heteroarylamine group, and the substituted C3-C25 heteroaryl group are each independently selected from the group consisting of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexane, cyclopentane, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl, or a combination of at least two thereof;

[0042] Preferably, Ar is selected from substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C6-C18 arylamine, substituted or unsubstituted C3-C18 heteroarylamine, substituted or unsubstituted C3-C18 heteroaryl;

[0043] Wherein, the substituents in the substituted C6-C18 aryl, substituted C6-C18 arylamine, substituted C3-C18 heteroarylamine, and substituted C3-C18 heteroaryl are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0044] Preferably, the substituents in the substituted C6-C18 aryl, substituted C6-C18 arylamine, substituted C3-C18 heteroarylamine, and substituted C3-C18 heteroaryl are selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexane, cyclopentane, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl;

[0045] Preferably, Ar is selected from a substituted or unsubstituted B group, and the B group is selected from the following groups: phenyl, naphthyl, biphenyl, phenanthryl, fluoranthene, yl, terphenyl, triphenylene, phenalenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenylmethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, benzonaphthofuranyl, benzonaphthothienyl, spiro[fluorene-9,9'-xanthenyl]yl, phenylmethylfluorenyl, dinaphthofuranyl, dinaphthothienyl, dibenzothienyl, N,N-diphenylanilinoyl;

[0046] Wherein, the substituent in the substituted B group is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, C3-C60 heteroarylamine;

[0047] Preferably, the substituent of the substituted B group is selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropyl, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthryl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl;

[0048] Preferably, L is selected from a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group;

[0049] Wherein, the substituents in the substituted C6-C30 arylene group and the substituted C3-C30 heteroarylene group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0050] Preferably, L is selected from substituted or unsubstituted C6-C25 arylene, substituted or unsubstituted C3-C25 heteroarylene;

[0051] Wherein, the substituents in the substituted C6-C25 arylene group and the substituted C3-C25 heteroarylene group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0052] Preferably, the substituents in the substituted C6-C25 arylene group and the substituted C3-C25 heteroarylene group are selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexane, cyclopentane, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl;

[0053] Preferably, L is selected from substituted or unsubstituted C6-C18 arylene, substituted or unsubstituted C3-C18 heteroarylene;

[0054] Wherein, the substituents in the substituted C6-C18 arylene group and the substituted C3-C18 heteroarylene group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0055] Preferably, the substituents in the substituted C6-C18 arylene group and the substituted C3-C18 heteroarylene group are selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexane, cyclopentanyl, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl.

[0056] Preferably, L is selected from a substituted or unsubstituted C group, and the C group is selected from the following groups: phenylene, naphthylene, biphenylene, phenanthrenyl, dibenzofuranyl, dibenzothiophenylene;

[0057] Wherein, the substituent of the substituted C group is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, C3-C60 heteroarylamine;

[0058] Preferably, the substituent of the substituted C group is selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexane, cyclopentane, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl.

[0059] Preferably, the deuterated oxazole ring organic compound is selected from any one of Formula 1-1 to Formula 1-25:

[0060]

[0061]

[0062]

[0063] Preferably, the formula 1-1 to formula 1-3 are selected from any one of formula A-1-1 to formula A-1-30:

[0064]

[0065]

[0066] Preferably, the deuterated oxazole ring organic compound is selected from any of the following structures:

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082] For the above N-396~N-415 structures, take N-396 as an example. D1-D21 means that other structures except the benzene ring B in the structure may be substituted by 1-21 deuteriums, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20 or 21 deuteriums.

[0083] Optionally, the deuteration rate of the above-mentioned compound is 1%-100%.

[0084] Optionally, the deuteration rate of the above-mentioned compound is 5%-100%.

[0085] Optionally, the deuteration rate of the above-mentioned compound is 10%-100%.

[0086] Optionally, the deuteration rate of the above-mentioned compound is 15%-100%.

[0087] Optionally, the deuteration rate of the above-mentioned compound is 20%-100%.

[0088] Optionally, the deuteration rate of the above-mentioned compound is 25%-100%.

[0089] Optionally, the deuteration rate of the above-mentioned compound is 30%-100%.

[0090] The deuteration rate represents the ratio of hydrogen to deuterium in the compound. It is understood that if a compound contains x deuterium atoms and y hydrogen atoms, the deuteration rate of the compound can be expressed as 100%*x / (x+y).

[0091] In the present invention, the deuterated oxazole ring organic compound having the structure of formula (1) is prepared by the following synthetic route:

[0092] 1. Synthesis of intermediate sub-n-1: The reaction formula is as follows:

[0093]

[0094] 2. Synthesis of compound Nn: The reaction formula is as follows:

[0095]

[0096] The raw materials ax, bx, cx, and dx can be purchased directly or synthesized by conventional reaction pathways and conditions with reference to existing literature reports.

[0097] The present invention also provides an organic electroluminescent material, comprising the deuterated oxazole ring organic compound as described above.

[0098] Preferably, the organic electroluminescent material includes a first host material and a second host material.

[0099] Preferably, the first host material is the deuterated oxazole ring organic compound mentioned above, and the second host material is an organic electroluminescent compound having the following structure (2):

[0100]

[0101] In the formula (2), Ar 1 Selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0102] The substituents in the substituted C6-C60 aryl group and the substituted C3-C630 heteroaryl group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0103] Preferably, Ar 1 A substituted or unsubstituted C6-C60 non-condensed aryl group, a substituted or unsubstituted C3-C60 non-condensed heteroaryl group;

[0104] The substituents in the substituted C6-C60 non-fused aryl group and the substituted C3-C60 non-fused heteroaryl group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0105] Preferably, Ar 1 is selected from a substituted or unsubstituted C6-C20 non-condensed aryl group, a substituted or unsubstituted C3-C20 non-condensed heteroaryl group;

[0106] The substituents in the substituted C6-C20 non-fused aryl group and the substituted C3-C20 non-fused heteroaryl group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0107] Preferably, Ar 1 A is selected from a substituted or unsubstituted A group, wherein the A group is selected from one of the following groups: phenyl, biphenyl, terphenyl;

[0108] wherein the substituent in the substituted A group is selected from deuterium, phenyl, and naphthyl;

[0109] Preferably, Ar 1Selected from phenyl, biphenyl, terphenyl, naphthylphenyl.

[0110] Preferably, the organic electroluminescent compound having the structure of the following formula (2) is selected from any one of the following M-1 to M-104:

[0111]

[0112]

[0113]

[0114]

[0115]

[0116] The second host material is a known compound.

[0117] Preferably, the mass ratio of the first main material to the second main material is 9:1-1:9;

[0118] Preferably, the mass ratio of the first main material to the second main material is 2:8-8:2;

[0119] More preferably, the mass ratio of the first main material to the second main material is 3:7-7:3;

[0120] Further preferably, the mass ratio of the first main material to the second main material is 4:6-6:4.

[0121] The present invention also provides an organic electroluminescent device, which comprises a cathode, an anode and an organic layer located between the cathode and the anode, wherein the organic layer comprises the above-mentioned deuterated oxazole ring organic compound or the above-mentioned organic electroluminescent material.

[0122] Preferably, the organic layer located between the cathode and the anode includes any one or a combination of at least two of a hole injection layer, a hole transport layer, a luminescence auxiliary layer, a luminescent layer, a hole blocking layer, an electron transport layer and an electron injection layer.

[0123] Optionally, the organic layer includes a hole injection layer to enhance the ability to inject holes into the hole transport layer. The hole injection layer can be made of benzidine derivatives, arylamine compounds, phthalocyanine derivatives or other materials, and this application does not impose any special restrictions on this. The materials of the hole injection layer include but are not limited to the following compounds:

[0124]

[0125]

[0126] Optionally, the organic layer includes a hole transport layer, which may include one or more hole transport materials, and the hole transport material may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, and the present application does not impose any special restrictions on this. The materials of the hole injection layer include but are not limited to the following compounds:

[0127]

[0128]

[0129] Optionally, the organic layer includes a light-emitting auxiliary layer, and the light-emitting auxiliary layer may be a single-layer or multi-layer structure.

[0130] Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises a deuterated oxazole ring organic compound as shown in formula (1) or the organic electroluminescent material as described above.

[0131] Preferably, the light-emitting layer includes a host material and a guest material, the host material includes the deuterated oxazole ring organic compound as described above or the host material in the organic electroluminescent material as described above, and the guest material can be a compound with a condensed aromatic ring or a derivative thereof, a compound with a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other material, and the present application does not impose any special restrictions on this. The guest material is also called a doping material or a dopant. According to the type of luminescence, it can be divided into a fluorescent dopant and a phosphorescent dopant. Specific examples of the phosphorescent dopant include, but are not limited to, the following structures:

[0132]

[0133]

[0134] Optionally, the organic layer includes a hole blocking layer, and the hole blocking layer may be a single-layer or multi-layer structure.

[0135] Optionally, the organic layer includes an electron transport layer, which may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from but not limited to LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, and the present application does not make any special restrictions on this. The materials of the electron transport layer include but are not limited to the following structures:

[0136]

[0137]

[0138] Optionally, an electron injection layer is provided between the cathode and the electron transport layer to enhance the ability to inject electrons into the electron transport layer. The electron injection layer may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include a complex of alkali metals and organic matter.

[0139] The present invention also provides an electronic device, characterized in that the electronic device comprises the organic electroluminescent device as described above or the organic electroluminescent material as described above or the organic compound as shown in formula (1).

[0140] The present invention also provides the use of the above-mentioned organic electroluminescent device in optical fiber equipment, lighting equipment, electronic photographic photosensitive body equipment, photoelectric converter, organic solar cell, switch element equipment, organic light-emitting field effect transistor, image sensor or dye laser.

[0141] Beneficial effects of the present invention:

[0142] The present invention provides a deuterated oxazole ring organic compound, which is based on the structure of formula (1). By introducing deuterium atoms into the compound shown in formula (1), the stability of the organic compound can be effectively improved, thereby extending the life of the device; and the present invention further limits the position of deuteration, so that the HOMO and LUMO energy levels of the organic compound are better matched with the adjacent energy levels, and the carrier mobility is better balanced, so that the device has a longer life while having the advantages of low voltage and high efficiency. In summary, the deuterated oxazole ring organic compound provided by the present invention has excellent properties, so that the prepared organic light-emitting device has the characteristics of low driving voltage, high luminous efficiency and long service life. BRIEF DESCRIPTION OF THE DRAWINGS

[0143] In order to more clearly illustrate the specific implementation methods of the present invention or the technical solutions in the prior art, the drawings required for use in the specific implementation methods or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are some implementation methods of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying creative work.

[0144] Figure 1 A structural diagram of an organic electroluminescent device in an embodiment of the device of the present invention;

[0145] 1-substrate; 2-anode; 3-hole injection layer; 4-hole transport layer; 5-light-emitting layer; 6-electron transport layer; 7-electron injection layer; 8-cathode. DETAILED DESCRIPTION

[0146] The following examples are provided for a better understanding of the present invention, but are not intended to limit the best mode of implementation, nor to limit the content and protection scope of the present invention. Any product identical or similar to the present invention obtained by anyone under the inspiration of the present invention or by combining the features of the present invention with other prior arts shall fall within the protection scope of the present invention.

[0147] If no specific experimental steps or conditions are specified in the examples, the conventional experimental steps or conditions described in the literature in the field can be used. If no manufacturer is specified for the reagents or instruments used, they are all conventional reagent products that can be obtained commercially.

[0148] The specific structures of the raw materials ax, bx, cx, and dx used in the embodiments of the present invention are as follows:

[0149] In the embodiment of the present invention, the raw material ax comprises the following structure:

[0150]

[0151] In the embodiment of the present invention, the raw material bx comprises the following structure:

[0152]

[0153] In the embodiment of the present invention, the raw material cx comprises the following structure:

[0154]

[0155] In the embodiment of the present invention, the raw material dx comprises the following structure:

[0156]

[0157] The preparation method of the required intermediate is as follows:

[0158] 1. Synthesis of intermediate sub-16-1:

[0159]

[0160] After nitrogen substitution in a three-necked reaction flask equipped with mechanical stirring, a thermometer, and a condenser, 10 g of raw material a-1 (36.63 mmol), 5.72 g of raw material b-1 (36.63 mmol), 0.85 g of tetrakistriphenylphosphine palladium (0.73 mmol), 10.11 g of potassium carbonate (73.27 mmol), 70 mL of toluene, 30 mL of ethanol, and 30 mL of water were added in sequence. The mixture was stirred at 65 ° C for 2 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and the residual moisture was removed by using anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 10.06 g of compound sub-16-1 (yield 90%).

[0161] Referring to the synthesis method of the intermediate sub-16-1, the raw material a-1 is replaced by the raw material ax, and the raw material b-1 is replaced by bx to obtain the different intermediates sub-n-1 shown in Table 1:

[0162] Table 1

[0163]

[0164]

[0165]

[0166] Example 1

[0167] This example provides the synthesis of compound N-16, referring to the following reaction formula, comprising the following steps:

[0168]

[0169] Synthesis of intermediate sub-16-2: After nitrogen substitution in a three-necked reaction bottle equipped with a mechanical stirrer, a thermometer, and a condenser, 10 g of intermediate sub-16-1 (32.78 mmol), 7.2 g of raw material c-1 (32.78 mmol), 0.6 g of tris(dibenzylideneacetone)dipalladium (0.66 mmol), 0.67 g of 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (1.64 mmol), 6.3 g of sodium tert-butoxide (65.56 mmol), and 100 mL of toluene were added in sequence, and the mixture was refluxed and stirred at 110° C. for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and the residual moisture was removed by using anhydrous sodium sulfate, the residue was dried and purified by column chromatography to obtain 12.97 g of compound sub-16-2 (yield 81%).

[0170] Synthesis of compound N-16: After nitrogen replacement in a three-necked reaction bottle equipped with a mechanical stirrer, a thermometer, and a condenser, 13.11 g of intermediate sub-16-2 (26.85 mmol), 7.03 g of raw material d-1 (26.85 mmol), 0.49 g of tris (dibenzylideneacetone) palladium (0.54 mmol), 0.55 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.34 mmol), 5.16 g of sodium tert-butoxide (53.70 mmol), 100 mL of toluene were added in sequence, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and the residual moisture was removed by using anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 14.76 g of compound N-16 (yield 77%).

[0171] Elemental analysis: C 51 H 23 D9N2O2; theoretical value: C, 85.81; H, 5.79; N, 3.92; O, 4.48; found value: C, 85.76; H, 5.780; N, 3.94; HRMS (ESI) m / z [M+H] +: theoretical value: 713.30; found value: 714.89.

[0172] Example 2

[0173] This example provides the synthesis of compound N-21, referring to the following reaction formula, comprising the following steps:

[0174]

[0175] Synthesis of intermediate sub-21-2: The synthesis steps of intermediate sub-21-2 are the same as those of intermediate sub-16-2, except that raw material c-1 is replaced by raw material c-2 to obtain intermediate sub-21-2 (yield 79%).

[0176] Synthesis of compound N-21: The synthesis steps of compound N-21 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by the intermediate sub-21-2, and the raw material d-1 is replaced by the raw material d-2, to obtain compound N-21 (yield 78%).

[0177] Elemental analysis: C 47 H 21 D9N2O2; theoretical value: C, 85.04; H, 5.92; N, 4.22; O, 4.82; found value: C, 85.02; H, 5.89; N, 4.24; HRMS (ESI) m / z [M+H] +: theoretical value: 663.29; found value: 665.01.

[0178] Example 3

[0179] This example provides the synthesis of compound N-30, referring to the following reaction formula, comprising the following steps:

[0180]

[0181] Synthesis of intermediate sub-30-2: The synthesis steps of intermediate sub-30-2 are the same as those of intermediate sub-16-2, except that raw material c-1 is replaced by raw material c-3 to obtain intermediate sub-30-2 (yield 81%).

[0182] Synthesis of compound N-30: The synthesis steps of compound N-30 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by the intermediate sub-30-2, and the raw material d-1 is replaced by the raw material d-3, to obtain compound N-30 (yield 77%).

[0183] Elemental analysis: C 45 H 21 D7N2O2; theoretical value: C, 85.01; H, 5.55; N, 4.41; O, 5.03; found value: C, 85.02; H, 5.56; N, 4.98; HRMS (ESI) m / z [M+H] +: theoretical value: 635.26; found value: 636.64.

[0184] Example 4

[0185] This example provides the synthesis of compound N-38, referring to the following reaction formula, comprising the following steps:

[0186]

[0187] Synthesis of intermediate sub-38-2: The synthesis steps of intermediate sub-38-2 are the same as those of intermediate sub-16-2, except that intermediate sub-16-1 is replaced by intermediate sub-38-1, and raw material c-1 is replaced by raw material c-10, thereby obtaining intermediate sub-38-2 (yield 82%).

[0188] Synthesis of compound N-38: The synthesis steps of compound N-38 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by the intermediate sub-38-2, and the raw material d-1 is replaced by the raw material d-4, thereby obtaining compound N-38 (yield 77%).

[0189] Elemental analysis: C 41 H 16D 10 N2O2; theoretical value: C, 83.65; H, 6.16; N, 4.76; O, 5.44; found value: C, 83.61; H, 6.17; N, 4.77; HRMS (ESI) m / z [M+H] +: theoretical value: 588.26; found value: 589.67.

[0190] Example 5

[0191] This example provides the synthesis of compound N-39, referring to the following reaction formula, comprising the following steps:

[0192]

[0193] Synthesis of intermediate sub-39-2: The synthesis steps of intermediate sub-39-2 are the same as those of intermediate sub-16-2, except that raw material c-1 is replaced by raw material c-4 to obtain intermediate sub-39-2 (yield 80%).

[0194] Synthesis of compound N-39: The synthesis steps of compound N-39 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by the intermediate sub-39-2, and the raw material d-1 is replaced by the raw material d-5, thereby obtaining compound N-39 (yield 79%).

[0195] Elemental analysis: C 51 H 19 D 13 N2O2; theoretical value: C, 85.33; H, 6.31; N, 3.90; O, 4.46; found value: C, 85.34; H, 6.27; N, 3.92; HRMS (ESI) m / z [M+H] +: theoretical value: 717.33; found value: 718.94.

[0196] Example 6

[0197] This example provides the synthesis of compound N-81, referring to the following reaction formula, comprising the following steps:

[0198]

[0199] Synthesis of intermediate sub-81-2: The synthesis steps of intermediate sub-81-2 are the same as those of intermediate sub-16-2, except that intermediate sub-16-1 is replaced by intermediate sub-81-1, and raw material c-1 is replaced by raw material c-5, to obtain intermediate sub-81-2 (yield 77%).

[0200] Synthesis of compound N-81: The synthesis steps of compound N-81 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by the intermediate sub-81-2, and the raw material d-1 is replaced by the raw material d-6, to obtain compound N-81 (yield 77%).

[0201] Elemental analysis: C 45 H 24 D4N2O2; theoretical value: C, 85.42; H, 5.10; N, 4.43; O, 5.06; found value: C, 85.43; H, 5.10; N, 4.40; HRMS (ESI) m / z [M+H] +: theoretical value: 632.24; found value: 633.35.

[0202] Example 7

[0203] This example provides the synthesis of compound N-140, referring to the following reaction formula, comprising the following steps:

[0204]

[0205] Synthesis of intermediate sub-140-2: The synthesis steps of intermediate sub-140-2 are the same as those of intermediate sub-16-2, except that intermediate sub-16-1 is replaced by intermediate sub-140-1, and raw material c-1 is replaced by raw material c-6, to obtain intermediate sub-140-2 (yield 75%).

[0206] Synthesis of compound N-140: The synthesis steps of compound N-140 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by the intermediate sub-140-2, and the raw material d-1 is replaced by the raw material d-7, thereby obtaining compound N-140 (yield 80%).

[0207] Elemental analysis: C 53 H 31 D4N3O2; theoretical value: C, 84.89; H, 5.24; N, 5.60; O, 4.27; found value: C, 84.87; H, 5.22; N, 5.63; HRMS (ESI) m / z [M+H] +: theoretical value: 749.30; found value: 750.69.

[0208] Example 8

[0209] This example provides the synthesis of compound N-142, referring to the following reaction formula, comprising the following steps:

[0210]

[0211] Synthesis of compound N-142: The synthesis steps of compound N-142 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by the intermediate sub-81-2, and the raw material d-1 is replaced by the raw material d-8, thereby obtaining compound N-142 (yield 78%).

[0212] Elemental analysis: C 45 H 24 D4N2O2; theoretical value: C, 85.42; H, 5.10; N, 4.43; O, 5.06; found value: C, 85.43; H, 5.10; N, 4.42; HRMS (ESI) m / z [M+H] +: theoretical value: 632.24; found value: 633.40.

[0213] Example 9

[0214] This example provides a synthesis of compound N-179, referring to the following reaction formula, comprising the following steps:

[0215]

[0216] Synthesis of intermediate sub-179-2: The synthesis steps of intermediate sub-179-2 are the same as those of intermediate sub-16-2, except that intermediate sub-16-1 is replaced by intermediate sub-140-1, and raw material c-1 is replaced by raw material c-7, thereby obtaining intermediate sub-179-2 (yield 74%).

[0217] Synthesis of compound N-179: The synthesis steps of compound N-179 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by the intermediate sub-179-2, and the raw material d-1 is replaced by the raw material d-9, thereby obtaining compound N-179 (yield 79%).

[0218] Elemental analysis: C 53 H 25 D 10 N3O2; theoretical value: C, 84.21; H, 6.00; N, 5.56; O, 4.23; found value: C, 84.20; H, 6.02; N, 5.54; HRMS (ESI) m / z [M+H] +: theoretical value: 755.34; found value: 756.72.

[0219] Example 10

[0220] This example provides a synthesis of compound N-191, referring to the following reaction formula, comprising the following steps:

[0221]

[0222] Synthesis of intermediate sub-191-2: The synthesis steps of intermediate sub-191-2 are the same as those of intermediate sub-16-2, except that intermediate sub-16-1 is replaced by intermediate sub-191-1, and raw material c-1 is replaced by raw material c-8, thereby obtaining intermediate sub-191-2 (yield 79%).

[0223] Synthesis of compound N-191: The synthesis steps of compound N-191 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by the intermediate sub-191-2, and the raw material d-1 is replaced by the raw material d-10, to obtain compound N-191 (yield 80%).

[0224] Elemental analysis: C 47 H 21 D7N2O3; theoretical value: C, 83.53; H, 5.22; N, 4.15; O, 7.10; found value: C, 83.53; H, 5.20; N, 4.16; HRMS (ESI) m / z [M+H] +: theoretical value: 675.25; found value: 676.65.

[0225] Embodiment 11

[0226] This example provides a synthesis of compound N-194, referring to the following reaction formula, comprising the following steps:

[0227]

[0228] Synthesis of intermediate sub-194-2: The synthesis steps of intermediate sub-194-2 are the same as those of intermediate sub-16-2, except that intermediate sub-16-1 is replaced by intermediate sub-191-1, and raw material c-1 is replaced by raw material c-5, thereby obtaining intermediate sub-194-2 (yield 81%).

[0229] Synthesis of compound N-194: The synthesis steps of compound N-194 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by the intermediate sub-194-2, and the raw material d-1 is replaced by the raw material d-11, thereby obtaining compound N-194 (yield 79%).

[0230] Elemental analysis: C 45 H 25D3N2O2; theoretical value: C, 85.56; H, 4.95; N, 4.43; O, 5.06; found value: C, 85.57; H, 4.96; N, 4.41; HRMS (ESI) m / z [M+H] +: theoretical value: 631.23; found value: 632.91.

[0231] Example 12

[0232] This example provides a synthesis of compound N-204, referring to the following reaction formula, comprising the following steps:

[0233]

[0234] Synthesis of intermediate sub-204-2: The synthesis steps of intermediate sub-204-2 are the same as those of intermediate sub-16-2, except that intermediate sub-16-1 is replaced by intermediate sub-204-1, and raw material c-1 is replaced by raw material c-9, thereby obtaining intermediate sub-204-2 (yield 80%).

[0235] Synthesis of compound N-204: The synthesis steps of compound N-204 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by the intermediate sub-204-2, and the raw material d-1 is replaced by the raw material d-12, thereby obtaining compound N-204 (yield 80%).

[0236] Elemental analysis: C 47 H 29 DN2O2; theoretical value: C, 86.08; H, 4.76; N, 4.27; O, 4.88; found value: C, 86.09; H, 4.77; N, 4.24; HRMS (ESI) m / z [M+H] +: theoretical value: 655.24; found value: 656.76.

[0237] Example 13

[0238] This example provides a synthesis of compound N-264, referring to the following reaction formula, comprising the following steps:

[0239]

[0240] Synthesis of intermediate sub-264-2: The synthesis steps of intermediate sub-264-2 are the same as those of intermediate sub-16-2, except that raw material c-1 is replaced by raw material c-10 to obtain intermediate sub-264-2 (yield 81%).

[0241] Synthesis of compound N-264: The synthesis steps of compound N-264 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by the intermediate sub-264-2, and the raw material d-1 is replaced by the raw material d-13, thereby obtaining compound N-264 (yield 80%).

[0242] Elemental analysis: C 41 H 15 D 11 N2O2; theoretical value: C, 83.50; H, 6.32; N, 4.75; O, 5.43; found value: C, 83.53; H, 6.31; N, 4.73; HRMS (ESI) m / z [M+H] +: theoretical value: 589.29; found value: 590.36.

[0243] Embodiment 14

[0244] This example provides a synthesis of compound N-270, referring to the following reaction formula, comprising the following steps:

[0245]

[0246] Synthesis of intermediate sub-270-2: The synthesis steps of intermediate sub-270-2 are the same as those of intermediate sub-16-2, except that intermediate sub-16-1 is replaced by intermediate sub-81-1, and raw material c-1 is replaced by raw material c-11, thereby obtaining intermediate sub-270-2 (yield 79%).

[0247] Synthesis of compound N-270: The synthesis steps of compound N-270 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by the intermediate sub-270-2, and the raw material d-1 is replaced by the raw material d-8, thereby obtaining compound N-270 (yield 80%).

[0248] Elemental analysis: C 53 H 28 D4N2O3; theoretical value: C, 85.01; H, 4.84; N, 3.74; O, 6.41; found value: C, 85.00; H, 4.85; N, 3.72; HRMS (ESI) m / z [M+H] +: theoretical value: 748.27; found value: 749.94.

[0249] Embodiment 15

[0250] This example provides a synthesis of compound N-277, referring to the following reaction formula, comprising the following steps:

[0251]

[0252] Synthesis of intermediate sub-277-2: The synthesis steps of intermediate sub-277-2 are the same as those of intermediate sub-16-2, except that intermediate sub-16-1 is replaced by intermediate sub-277-1, and raw material c-1 is replaced by raw material c-12, thereby obtaining intermediate sub-277-2 (yield 76%).

[0253] Synthesis of compound N-277: The synthesis steps of compound N-277 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by the intermediate sub-277-2, and the raw material d-1 is replaced by the raw material d-14, thereby obtaining compound N-277 (yield 75%).

[0254] Elemental analysis: C 52 H 31 D5N2O2; theoretical value: C, 86.04; H, 5.69; N, 3.86; O, 4.41; found value: C, 86.00; H, 5.70; N, 3.87; HRMS (ESI) m / z [M+H] +: theoretical value: 725.31; found value: 726.48.

[0255] Example 16

[0256] This example provides the synthesis of compound N-281, referring to the following reaction formula, comprising the following steps:

[0257]

[0258] Synthesis of intermediate sub-281-2: The synthesis steps of intermediate sub-281-2 are the same as those of intermediate sub-16-2, except that intermediate sub-16-1 is replaced by intermediate sub-281-1, and raw material c-1 is replaced by raw material c-12, thereby obtaining intermediate sub-281-2 (yield 76%).

[0259] Synthesis of compound N-281: The synthesis steps of compound N-281 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by the intermediate sub-281-2, and the raw material d-1 is replaced by the raw material d-14, to obtain compound N-281 (yield 75%).

[0260] Elemental analysis: C 51 H 26D4N2O3; theoretical value: C, 84.74; H, 4.74; N, 3.88; O, 6.64; found value: C, 84.76; H, 4.74; N, 3.84; HRMS (ESI) m / z [M+H] +: theoretical value: 722.25; found value: 723.68.

[0261] Embodiment 17

[0262] This example provides a synthesis of compound N-285, referring to the following reaction formula, comprising the following steps:

[0263]

[0264] Synthesis of intermediate sub-285-2: The synthesis steps of intermediate sub-285-2 are the same as those of intermediate sub-16-2, except that raw material c-1 is replaced by raw material c-14 to obtain intermediate sub-285-2 (yield 81%).

[0265] Synthesis of compound N-285: The synthesis steps of compound N-285 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by the intermediate sub-285-2, and the raw material d-1 is replaced by the raw material d-16, to obtain compound N-285 (yield 80%).

[0266] Elemental analysis: C 43 H 25 D1N2O3; theoretical value: C, 83.34; H, 4.39; N, 4.52; O, 7.75; found value: C, 83.34; H, 4.39; N, 4.52; HRMS (ESI) m / z [M+H] +: theoretical value: 619.20; found value: 620.33.

[0267] Embodiment 18

[0268] This example provides a synthesis of compound N-301, referring to the following reaction formula, comprising the following steps:

[0269]

[0270] Synthesis of intermediate sub-301-2: The synthesis steps of intermediate sub-301-2 are the same as those of intermediate sub-16-2, except that intermediate sub-16-1 is replaced by intermediate sub-281-1, and raw material c-1 is replaced by raw material c-15, to obtain intermediate sub-301-2 (yield 78%).

[0271] Synthesis of compound N-301: The synthesis steps of compound N-301 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by the intermediate sub-301-2, and the raw material d-1 is replaced by the raw material d-17, thereby obtaining compound N-301 (yield 78%).

[0272] Elemental analysis: C 51 H 28 D4N2O2; theoretical value: C, 86.42; H, 5.12; N, 3.95; O, 4.51; found value: C, 86.38; H, 5.14; N, 3.93; HRMS (ESI) m / z [M+H] +: theoretical value: 708.27; found value: 709.44.

[0273] Embodiment 19

[0274] This example provides a synthesis of compound N-314, referring to the following reaction formula, comprising the following steps:

[0275]

[0276] Synthesis of intermediate sub-314-2: The synthesis steps of intermediate sub-314-2 are the same as those of intermediate sub-16-2, except that intermediate sub-16-1 is replaced by intermediate sub-191-1, and raw material c-1 is replaced by raw material c-16, to obtain intermediate sub-314-2 (yield 81%).

[0277] Synthesis of compound N-314: The synthesis steps of compound N-314 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by the intermediate sub-314-2, and the raw material d-1 is replaced by the raw material d-18, thereby obtaining compound N-314 (yield 79%).

[0278] Elemental analysis: C 55 H 27 D7N2O2; theoretical value: C, 86.70; H, 5.42; N, 3.68; O, 4.20; found value: C, 86.71; H, 5.44; N, 3.64; HRMS (ESI) m / z [M+H] +: theoretical value: 761.31; found value: 762.85.

[0279] Embodiment 20

[0280] This example provides a synthesis of compound N-333, referring to the following reaction formula, comprising the following steps:

[0281]

[0282] Synthesis of intermediate sub-333-2: The synthesis steps of intermediate sub-333-2 are the same as those of intermediate sub-16-2, except that intermediate sub-16-1 is replaced by intermediate sub-333-1, and raw material c-1 is replaced by raw material c-17, thereby obtaining intermediate sub-333-2 (yield 82%).

[0283] Synthesis of compound N-333: The synthesis steps of compound N-333 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by the intermediate sub-333-2, and the raw material d-1 is replaced by the raw material d-19, thereby obtaining compound N-333 (yield 75%).

[0284] Elemental analysis: C 55 H 29 D5N2O2; theoretical value: C, 86.93; H, 5.17; N, 3.69; O, 4.21; found value: C, 86.89; H, 5.18; N, 3.71; HRMS (ESI) m / z [M+H] +: theoretical value: 759.29; found value: 760.71.

[0285] Embodiment 21

[0286] This example provides the synthesis of compound N-382, referring to the following reaction formula, comprising the following steps:

[0287]

[0288] Synthesis of intermediate sub-382-2: The synthesis steps of intermediate sub-382-2 are the same as those of intermediate sub-16-2, except that intermediate sub-16-1 is replaced by intermediate sub-382-1, and raw material c-1 is replaced by raw material c-18, thereby obtaining intermediate sub-382-2 (yield 78%).

[0289] Synthesis of compound N-382: The synthesis steps of compound N-382 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by the intermediate sub-382-2, and the raw material d-1 is replaced by the raw material d-8, thereby obtaining compound N-382 (yield 77%).

[0290] Elemental analysis: C 57 H 30D4N2O2S; theoretical value: C, 84.00; H, 4.70; N, 3.44; O, 3.93; S, 3.93; found value: C, 84.01; H, 4.68; N, 3.46; S, 3.92; HRMS (ESI) m / z [M+H] +: theoretical value: 814.26; found value: 815.51.

[0291] Device Examples

[0292] The present invention also provides an OLED device composed of different organic electroluminescent materials, the specific structure of which is as follows: Figure 1 As shown, the OLED device has the following layer structure: substrate (glass substrate) 1 / anode 2 (indium tin oxide (ITO) coating coated on the glass substrate) / hole injection layer 3 (HIL) / hole transport layer 4 (HTL) / light-emitting layer 5 (EML) / electron transport layer 6 (ETL) / electron injection layer 7 (EIL) / cathode 8.

[0293] The materials for some of the device examples are selected from the following:

[0294]

[0295] The preparation method of the OLED device comprises the following steps:

[0296] (1) Substrate cleaning:

[0297] The glass substrate coated with transparent ITO is ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤ 10wt%, triethanolamine ≤ 1wt%), rinsed in deionized water, ultrasonically degreased in an acetone: ethanol mixed solvent (volume ratio 1:1), baked in a clean environment until the water is completely removed, and then cleaned with ultraviolet light and ozone.

[0298] (2) Evaporation of organic light-emitting functional layer:

[0299] The glass substrate with the anode layer is placed in a vacuum chamber and evacuated to 1×10 -6 Up to 2×10 -4 Pa, vacuum evaporating a mixture of HI-8 and HT-10 on the above anode layer film, wherein the mass ratio of HI-8 to HT-10 is 3:97, as a hole injection layer, the evaporation thickness is 10 nm;

[0300] A hole transport layer (made of HT-10) is evaporated on the hole injection layer, with a thickness of 80 nm.

[0301] The light-emitting layer is deposited on the hole transport layer. The specific preparation method is as follows: vacuum-deposit the light-emitting host material (the materials are shown in Table 2) and the guest material RD-12 in a co-evaporation manner, and the total film thickness of the deposition is 38 nm.

[0302] An electron transport layer is evaporated on the light-emitting layer. The specific preparation method is: vacuum evaporation of ET-4 and LiQ in a co-evaporation manner, wherein the mass ratio of ET-4 to LiQ is 50:50, and the total evaporation film thickness is 30 nm;

[0303] An electron injection layer (made of LiQ) is vacuum-deposited on the electron transport layer, with a total film thickness of 1 nm.

[0304] Al was evaporated on the electron injection layer, and the total film thickness of the evaporated layer was 90 nm.

[0305] The main material structures used in the device comparison examples are shown below:

[0306]

[0307] REF-2 can be prepared by the following steps:

[0308]

[0309] Synthesis of intermediate sub-REF-2: The synthesis steps of intermediate sub-REF-2 are the same as those of intermediate sub-16-2, except that intermediate sub-16-1 is replaced by intermediate sub-38-1, and raw material c-1 is replaced by raw material c-2, thereby obtaining intermediate sub-REF-2 (yield 80%).

[0310] Synthesis of compound REF-2: The synthesis steps of compound REF-2 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by intermediate sub-REF-2, and the raw material d-1 is replaced by raw material d-20, to obtain compound REF-2 (yield 79%).

[0311] Elemental analysis: C 47 H 25 D5N2O2; theoretical value: C, 85.56; H, 5.35; N, 4.25; O, 4.85; found value: C, 85.58; H, 5.34; N, 4.23; HRMS (ESI) m / z [M+H] +: theoretical value: 659.80; found value: 660.94.

[0312] REF-3 can be prepared by the following steps:

[0313]

[0314] Synthesis of intermediate sub-REF-3: The synthesis steps of intermediate sub-REF-3 are the same as those of intermediate sub-16-2, except that intermediate sub-16-1 is replaced by intermediate sub-191-1, and raw material c-1 is replaced by raw material c-19, to obtain intermediate sub-REF-3 (yield 80%).

[0315] Synthesis of compound REF-3: The synthesis steps of compound REF-3 are the same as those of compound N-16, except that the intermediate sub-16-2 is replaced by intermediate sub-REF-3, and the raw material d-1 is replaced by raw material d-18, thereby obtaining compound REF-3 (yield 80%).

[0316] Elemental analysis: C 55 H 34 N2O2; theoretical value: C, 87.51; H, 4.54; N, 3.71; O, 4.24; found value: C, 87.54; H, 4.52; N, 3.70; HRMS (ESI) m / z [M+H] +: theoretical value: 754.89; found value: 756.01.

[0317] Parameters such as materials and thickness of each layer in device embodiments 1-26 and device comparative examples 1-9 are shown in Table 2 below:

[0318] Table 2

[0319]

[0320]

[0321]

[0322]

[0323]

[0324] The organic electroluminescent devices obtained from device examples 1-23 and device comparative examples 1-6 were tested.

[0325] Instruments: The device's current, voltage, brightness, luminous spectrum and other characteristics are tested synchronously using a PR650 spectrum scanning luminance meter and a Keithley K2400 digital source meter system;

[0326] Test conditions: Photoelectric properties Test conditions: Current density is 10mA / cm 2 .

[0327] Life test: current density is 50mA / cm 2, record the time (in hours) when the device brightness drops to 95% of the original brightness.

[0328] The device performance test results are shown in Table 3, wherein the life test data of Comparative Example 1 in Table 3 is set to 100, and the life test data in Table 3 are all relative values ​​thereto:

[0329] Table 3

[0330] project Driving voltage(V) Current efficiency (Cd / A) Lifespan T95 Device Example 1 3.27 31.30 118.3 Device Example 2 3.24 32.43 124.1 Device Example 3 3.27 31.50 118.4 Device Example 4 3.27 31.97 124.6 Device Example 5 3.26 31.77 119.0 Device Example 6 3.21 31.81 117.6 Device Example 7 3.20 32.25 128.4 Device Example 8 3.25 31.78 120.4 Device Example 9 3.19 32.54 129.5 Device Example 10 3.21 32.35 130.4 Device Example 11 3.25 31.70 121.3 Device Example 12 3.27 32.01 119.3 Device Example 13 3.26 31.84 123.5 Device Example 14 3.27 32.10 121.3 Device Example 15 3.19 32.79 129.8 Device Example 16 3.23 32.56 125.4 Device Example 17 3.45 29.94 111.3 Device Example 18 3.27 32.03 120.7 Device Example 19 3.37 30.54 116.4 Device Example 20 3.48 29.89 110.6 Device Example 21 3.38 30.43 116.2 Device Example 22 3.37 30.46 117.4 Device Example 23 3.20 32.85 130.6 Device Comparative Example 1 3.30 31.29 100.0 Device Comparison Example 2 3.28 30.94 107.3 Device Comparison Example 3 3.40 30.04 98.7 Device Comparison Example 4 3.66 24.31 67.1 Device Comparison Example 5 3.59 25.09 69.6 Device Comparative Example 6 3.67 24.68 67.8

[0331] The organic electroluminescent devices obtained from device examples 24 to 26 and device comparative examples 7 to 9 were tested.

[0332] Instruments: The device's current, voltage, brightness, luminous spectrum and other characteristics are tested synchronously using a PR650 spectrum scanning luminance meter and a Keithley K2400 digital source meter system;

[0333] Test conditions: Photoelectric properties Test conditions: Current density is 10mA / cm 2 .

[0334] Life test: current density is 50mA / cm 2 , record the time (in hours) when the device brightness drops to 95% of the original brightness.

[0335] The device performance test results are shown in Table 4, wherein the life test data of Comparative Example 7 in Table 4 is set to 100, and the life test data in Table 4 are all relative values ​​thereto:

[0336] Table 4

[0337] project Driving voltage(V) Current efficiency (Cd / A) Lifespan T95 Device Example 24 3.90 13.01 141.7 Device Example 25 4.05 11.89 120.3 Device Example 26 3.93 12.86 153.2 Device Comparison Example 7 3.91 12.78 100.0 Device Comparison Example 8 4.01 11.97 113.5 Device Comparative Example 9 4.07 11.06 88.6

[0338] Obviously, the above embodiments are merely examples for the purpose of clear explanation, and are not intended to limit the implementation methods. For those skilled in the art, other different forms of changes or modifications can be made based on the above description. It is not necessary and impossible to list all the implementation methods here. The obvious changes or modifications derived therefrom are still within the scope of protection of the invention.

Claims

1. A deuterated oxazole ring organic compound, characterized in that: The organic compound has a structure shown in formula (1): In the formula (1), ring A may be present or absent, and when present, ring A is selected from a benzene ring, a naphthalene ring, a benzofuran ring or a benzothiophene ring; Ar is selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 arylamine group, a substituted or unsubstituted C3-C60 heteroarylamine group, or a substituted or unsubstituted C3-C60 heteroaryl group; L is selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group; R1 and R2 are deuterium; R3 is selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 arylamine group, a substituted or unsubstituted C3-C60 heteroarylamine group, a substituted or unsubstituted C3-C60 heteroaryl group, and / or is bonded to an adjacent group to form a ring; n1 is an integer selected from 0-12; n2 is an integer selected from 0-3; n3 is an integer selected from 0-5; The substituents in the substituted C6-C60 aryl, substituted C6-C60 arylamine, substituted C3-C60 heteroarylamine, substituted C3-C60 heteroaryl, substituted C6-C60 arylene, and substituted C3-C60 heteroarylene are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine; Wherein, formula (1) satisfies at least one of the following: n1+n2≥1; The deuteration rate of Ar is greater than 0; The deuteration rate of L is greater than 0.

2. The deuterated oxazole ring organic compound according to claim 1, characterized in that: Ar is selected from substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C6-C25 arylamine, substituted or unsubstituted C3-C25 heteroarylamine, substituted or unsubstituted C3-C25 heteroaryl; Wherein, the substituents in the substituted C6-C25 aryl, substituted C6-C25 arylamine, substituted C3-C25 heteroarylamine, and substituted C3-C25 heteroaryl are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine; Preferably, the substituents in the substituted C6-C25 aryl group, the substituted C6-C25 arylamine group, the substituted C3-C25 heteroarylamine group, and the substituted C3-C25 heteroaryl group are each independently selected from the group consisting of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexane, cyclopentane, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl, or a combination of at least two thereof; Preferably, L is selected from substituted or unsubstituted C6-C25 arylene, substituted or unsubstituted C3-C25 heteroarylene; Wherein, the substituents in the substituted C6-C25 arylene group and the substituted C3-C25 heteroarylene group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine; Preferably, the substituents in the substituted C6-C25 arylene group and the substituted C3-C25 heteroarylene group are selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexane, cyclopentanyl, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrene, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl.

3. The deuterated oxazole ring organic compound according to claim 1 or 2, characterized in that: Ar is selected from substituted or unsubstituted B groups, and B groups are selected from the following groups: phenyl, naphthyl, biphenyl, phenanthrenyl, fluoranthene, yl, terphenyl, triphenylene, phenalkenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenylmethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, benzonaphthofuranyl, benzonaphthothienyl, spiro[fluorene-9,9'-xanthenyl]yl, phenylmethylfluorenyl, dinaphthofuranyl, dinaphthothienyl, dibenzothienyl, N,N-diphenylanilinoyl; Wherein, the substituent in the substituted B group is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, C3-C60 heteroarylamine; Preferably, the substituent of the substituted B group is selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropyl, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthryl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl; Preferably, L is selected from a substituted or unsubstituted C group, and the C group is selected from the following groups: phenylene, naphthylene, biphenylene, phenanthrenyl, dibenzofuranyl, dibenzothiophenylene; Wherein, the substituent of the substituted C group is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, C3-C60 heteroarylamine; Preferably, the substituent of the substituted C group is selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexane, cyclopentane, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl.

4. The deuterated oxazole ring organic compound according to any one of claims 1 to 3, characterized in that: The structure represented by formula (1) is selected from any one of formulas 1-1 to 1-30, wherein the definitions of Ar, L, R1, R2, R3, n1, n2, and n3 are the same as those in claim 1:

5. The deuterated oxazole ring organic compound according to any one of claims 1 to 4, characterized in that: The deuterated oxazole ring organic compound is selected from any of the following structures:

6. An organic electroluminescent material, characterized in that: The organic electroluminescent material comprises the deuterated oxazole ring organic compound according to any one of claims 1 to 5.

7. The organic electroluminescent material according to claim 6, characterized in that: The organic electroluminescent material comprises a first host material and a second host material, wherein the first host material is a deuterated oxazole ring organic compound according to any one of claims 1 to 5; and the second host material is an organic electroluminescent compound having a structure of the following formula (2): In the formula (2), Ar 1 Selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; The substituents in the substituted C6-C60 aryl group and the substituted C3-C630 heteroaryl group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine; Preferably, Ar 1 A substituted or unsubstituted C6-C60 non-condensed aryl group, a substituted or unsubstituted C3-C60 non-condensed heteroaryl group; The substituents in the substituted C6-C60 non-fused aryl group and the substituted C3-C60 non-fused heteroaryl group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine; Preferably, Ar 1 is selected from a substituted or unsubstituted C6-C20 non-condensed aryl group, a substituted or unsubstituted C3-C20 non-condensed heteroaryl group; The substituents in the substituted C6-C20 non-fused aryl group and the substituted C3-C20 non-fused heteroaryl group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine; Preferably, Ar 1 A is selected from a substituted or unsubstituted A group, wherein the A group is selected from one of the following groups: phenyl, biphenyl, terphenyl; wherein the substituent in the substituted A group is selected from deuterium, phenyl, and naphthyl; Preferably, Ar 1 Selected from phenyl, biphenyl, terphenyl, naphthylphenyl.

8. The organic electroluminescent material according to claim 6 or 7, characterized in that: The mass ratio of the first main material to the second main material is 9:1-1:9; Preferably, the mass ratio of the first main material to the second main material is 2:8-8:2; More preferably, the mass ratio of the first main material to the second main material is 3:7-7:3; Further preferably, the mass ratio of the first main material to the second main material is 4:6-6:

4.

9. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises a cathode, an anode and an organic layer between the cathode and the anode, wherein the organic layer comprises the deuterated oxazole ring organic compound according to any one of claims 1 to 5 or the organic electroluminescent material according to any one of claims 6 to 8; Preferably, the organic layer located between the cathode and the anode comprises any one or a combination of at least two of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer; Preferably, the hole transport layer comprises the deuterated oxazole ring organic compound according to any one of claims 1 to 5 or the organic electroluminescent material according to any one of claims 6 to 8; Preferably, the light-emitting layer comprises the deuterated oxazole ring organic compound according to any one of claims 1 to 5 or the organic electroluminescent material according to any one of claims 6 to 8.

10. Use of the organic electroluminescent device according to claim 9 in optical fiber equipment, lighting equipment, electrophotographic photosensitive body equipment, photoelectric converter, organic solar cell, switching element equipment, organic light emitting field effect transistor, image sensor or dye laser.

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