An imidazole compound and an organic electroluminescent device

Abstract

The present invention provides an imidazole compound and an organic electroluminescent device thereof, relating to the technical field of organic electroluminescent materials. The imidazole compound of Formula 1 in the present invention has good stability, relatively high triplet energy levels and good electron-transporting properties. When used as the host material of the light-emitting layer of an organic electroluminescent device, it can effectively balance electrons and holes in the light-emitting layer, enabling the two to effectively combine into excitons and emit light in the light-emitting layer, thereby reducing the driving voltage of the device, improving the light-emitting efficiency of the device, extending the service life of the device, and improving the performance of the device. In addition, when the imidazole compound of Formula 1 in the present invention is used as an electron-transporting material or a covering layer material, the performance of the device is also improved.

Description

Technical Field

[0001] The invention relates to the technical field of organic electroluminescent materials, and in particular to an imidazole compound and an organic electroluminescent device thereof. Background Art

[0002] OLED stands for Organic Light-Emitting Diode, which has the advantages of thin thickness, light weight, fast response speed, high color contrast, wide viewing angle, low power consumption, and flexible display. It is regarded as a promising new display product in the diversified flat panel display market.

[0003] OLED display technology is different from traditional LCD display. It does not require a backlight source. It uses very thin organic material films and glass substrates. When current passes through, these organic materials will emit light. The OLED light-emitting mechanism is as follows: under the action of an external electric field, electrons and holes are injected from the cathode and anode into the organic film layer sandwiched between the electrodes, and the injected electrons and holes migrate from the electron transport layer and the hole transport layer to the light-emitting layer, respectively. The electrons and holes recombine in the light-emitting layer to generate excitons, which generate photons and release energy through radiation transition.

[0004] According to the different organic functional materials used, OLED devices can be divided into two categories: small molecule devices and polymer devices. Small molecule OLED technology was developed earlier, and the technology has reached the level of commercial production and is currently in a leading position. Polymer OLED, also known as PLED, is far from mature and is currently in the research and development and small-scale production stage.

[0005] Organic electroluminescent devices are mainly composed of substrates, anodes, cathodes, and at least one functional layer of hole injection layer, hole transport layer, electron blocking layer, luminescent layer, hole blocking layer, electron transport layer, electron injection layer, and covering layer. Among them, the luminescent layer material (host material / guest material), the electron transport region material (hole blocking material, electron transport material, electron injection material) and the covering layer material play an important role in organic electroluminescent devices.

[0006] However, the performance of the organic functional materials currently used is mostly poor, resulting in problems such as high driving voltage, low luminous efficiency, and short service life in OLED devices. Therefore, how to improve the performance of organic functional materials to obtain better organic electroluminescent devices has become one of the key issues currently focused on by researchers. Summary of the invention

[0007] In view of the problems existing in the prior art, the present invention provides an imidazole compound and an organic electroluminescent device thereof.

[0008] The present invention provides an imidazole compound having a general structural formula as shown in Formula 1,

[0009]

[0010] Wherein, Ar is selected from the following groups,

[0011]

[0012] The A's are the same or different and are selected from C(Ra) or N, and the Ra's are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C35 aryl, substituted or unsubstituted C2-C35 heteroaryl, substituted or unsubstituted C3-C25 alicyclic and C6-C35 aromatic ring fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C35 heteroaromatic ring fused ring group, substituted or unsubstituted C3-C25 alicyclic heterocyclic group, and at least two adjacent Ra's are bonded to each other to form a substituted or unsubstituted ring;

[0013] The R 0 One selected from substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C35 aryl, substituted or unsubstituted C2-C35 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C6-C35 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C35 heteroaromatic ring, and a substituted or unsubstituted C3-C25 alicyclic heterocyclic group;

[0014] The R 1 One selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C35 aryl, substituted or unsubstituted C2-C35 heteroaryl, substituted or unsubstituted C3-C25 alicyclic and C6-C35 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C35 heteroaromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic heterocyclic group;

[0015] The A 1 , A 2 are independently selected from the groups shown below,

[0016]

[0017] The Bs are the same or different and are selected from C(Rb) or N, and the Rb are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C35 aryl, substituted or unsubstituted C2-C35 heteroaryl, substituted or unsubstituted C3-C25 alicyclic and C6-C35 aromatic ring fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C35 heteroaromatic ring fused ring group, substituted or unsubstituted C3-C25 alicyclic heterocyclic group, or two adjacent Rb are bonded to each other to form a substituted or unsubstituted ring;

[0018] The X 0 is selected from O or S; said E is selected from N or C(Re);

[0019] The Re, R 2 One independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C35 aryl, substituted or unsubstituted C2-C35 heteroaryl, substituted or unsubstituted C3-C25 alicyclic and C6-C35 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C35 heteroaromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic heterocyclic group;

[0020] The X are the same or different and are selected from C(Rx) or N, the R x One selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C35 aryl, substituted or unsubstituted C2-C35 heteroaryl, substituted or unsubstituted C3-C25 alicyclic and C6-C35 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C35 heteroaromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic heterocyclic group;

[0021] The L a , L b , L 1 , L 2The substituents are independently selected from a single bond, a substituted or unsubstituted C6-C35 arylene group, a substituted or unsubstituted C2-C35 heteroarylene group, a substituted or unsubstituted C3-C25 alicyclic and C6-C35 aromatic ring sub-condensed ring group, a substituted or unsubstituted C3-C25 alicyclic and C2-C35 heteroaromatic ring sub-condensed ring group, or a combination thereof; the substituents in the "substituted or unsubstituted" group are selected from the following groups: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 alicyclic heterocyclic group, or two adjacent substituents are bonded to each other to form a substituted or unsubstituted ring.

[0022] In addition, the present invention also provides an organic electroluminescent device, wherein the organic electroluminescent device contains the imidazole compound of the present invention.

[0023] Beneficial effects: The imidazole compound of formula 1 of the present invention has good stability, a high triplet energy level and good electron transport properties. When it is used as the main material of the light-emitting layer of an organic electroluminescent device, it can effectively balance the electrons and holes in the light-emitting layer, so that the two are effectively combined into excitons in the light-emitting layer to emit light, thereby reducing the driving voltage of the device, improving the luminous efficiency of the device, extending the service life of the device, and improving the performance of the device.

[0024] In addition, when the imidazole compound of Formula 1 of the present invention is used as an electron transport material or a covering layer material, the performance of the device is also improved. DETAILED DESCRIPTION

[0025] The present invention is further explained below in conjunction with specific embodiments. It should be understood that these embodiments are only used to illustrate the present invention and are not used to limit the scope of the present invention. After reading the present invention, various equivalent forms of modifications to the present invention by those skilled in the art all fall within the scope of protection required by this application.

[0026] In the compounds of the present invention, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes the atom in both its natural isotopic abundance and unnatural abundance.

[0027] In the present invention, when the position of a substituent on a ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the ring. For example, Can be expressed And so on.

[0028] In the present invention, when a substituent or a bond at a connection site runs through two or more rings, it indicates that it can be connected to any of the two or more rings, specifically, it can be connected to any of the corresponding optional sites of the ring. For example, Can be expressed Can be expressed And so on.

[0029] In the present invention, "two adjacent groups are bonded to form a ring" means that adjacent groups are bonded to each other and optionally aromatized to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. The hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle can include an aliphatic heterocycle or an aromatic heterocycle. The aliphatic hydrocarbon ring can be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle can be a saturated aliphatic heterocycle or an unsaturated aliphatic heterocycle. The hydrocarbon ring and the heterocycle can be monocyclic or polycyclic groups. In addition, the ring formed by the combination of adjacent groups can be connected to another ring to form a spiro structure. The following example is shown:

[0030]

[0031] In the present invention, the ring formed by connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a condensed ring, etc., for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclopentene, cyclohexene, benzene, naphthalene, phenanthrene, anthracene, triphenylene, pyridine, pyrimidine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, naphthylene, benzoquinoline, benzisoquinoline, phenanthridine, phenanthroline, azaanthracene, azatriphenylene, fluorene, furan, thiophene, carbazole, etc., but are not limited thereto.

[0032] In the present invention, when the fusion position of an aromatic ring or a heteroaromatic ring on the aromatic ring or the heteroaromatic ring is not fixed, it means that it can be fused to any corresponding feasible position of the aromatic ring or the heteroaromatic ring. For example, Can be expressed And so on.

[0033] The halogen described in the present invention includes fluorine, chlorine, bromine and iodine.

[0034] In the present invention, the "unsubstituted ZZ group" in the "substituted or unsubstituted ZZ group" means that the hydrogen atom of the "ZZ group" is not replaced by a substituent. For example, the "unsubstituted aryl group" in the "substituted or unsubstituted C6-C35 aryl group" means that the hydrogen atom of the "aryl group" is not replaced by a substituent. And so on.

[0035] In the present invention, "CXX-CYY" in "substituted or unsubstituted ZZ group of CXX-CYY" represents the number of carbon atoms in the unsubstituted "ZZ group", and when the "ZZ group" has a substituent, the number of carbon atoms of the substituent is not included. For example, "C6-C35" in "substituted or unsubstituted C6-C30 aryl group" represents the number of carbon atoms in the unsubstituted "aryl group", and when the "aryl group" has a substituent, the number of carbon atoms in the substituent is not included. "C3-C25" in "substituted or unsubstituted C3-C25 alicyclic ring and C6-C35 aromatic ring fused ring group" represents the number of carbon atoms in the unsubstituted "alicyclic ring", and when the "alicyclic ring" has a substituent, the number of carbon atoms of the substituent is not included; "C6-C35" represents the number of carbon atoms in the unsubstituted "aromatic ring", and when the "aromatic ring" has a substituent, the number of carbon atoms of the substituent is not included. And so on.

[0036] The "substituted" in the "substituted or unsubstituted" of the present invention means that at least one hydrogen atom on the group is replaced by a substituent. When multiple hydrogens are replaced by multiple substituents, the multiple substituents may be the same or different. The position of the hydrogen replaced by the above-mentioned substituent may be any position. The substituent represented by the "substituted" in the above-mentioned "substituted or unsubstituted" includes the following groups, deuterium, tritium, cyano, halogen, nitro, silanyl, alkoxy, aryloxy, heterocyclic group, alkyl, cycloalkyl, aryl, heteroaryl, fused ring group of alicyclic ring and aromatic ring, fused ring group of alicyclic ring and heteroaromatic ring, etc. Preferred are the following groups: deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, bornyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, anthracenyl, pyrenyl, fluorenyl, spirobifluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinoline , benzophenanthryl, benzocyclohexyl, benzocyclobutene, indenyl, dihydronaphthyl, tetrahydronaphthyl, benzocycloheptyl, benzocyclobutenyl, indenyl, dihydronaphthyl, etc. In addition, each of the above-mentioned substituents can be substituted or unsubstituted. Two adjacent substituents can be bonded to form a ring.

[0037] The alkyl group of the present invention refers to a hydrocarbon group formed by missing a hydrogen atom in an alkane molecule. The alkyl group may be a straight-chain alkyl group or a branched-chain alkyl group. And so on. Examples of the alkyl group include, but are not limited to, the groups described below, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, etc., but are not limited thereto. When the number of carbon atoms of the chain alkyl group of the present invention is three or more, its isomers are included, for example, butyl includes n-butyl, isobutyl, sec-butyl, and tert-butyl. Preferably, it has 1 to 25 carbon atoms, preferably 1 to 20 carbon atoms, preferably 1 to 15 carbon atoms, and preferably 1 to 10 carbon atoms.

[0038] The cycloalkyl group of the present invention refers to a hydrocarbon group formed by removing a hydrogen atom from a cycloalkane molecule. The cycloalkyl group includes a monocyclic cycloalkyl group, a polycyclic cycloalkyl group, and a bridged ring cycloalkyl group. Examples of the cycloalkyl group include, but are not limited to, the following groups, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, and camphenyl, but are not limited thereto. Preferably, the cycloalkyl group has 3 to 25 carbon atoms, preferably 3 to 20 carbon atoms, preferably 3 to 15 carbon atoms, and more preferably 3 to 10 carbon atoms.

[0039] The aryl group described in the present invention refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon of the aromatic compound molecule. The aryl group includes a monocyclic aryl group, a polycyclic aryl group, a condensed ring aryl group or a combination thereof. Examples of the aryl group include, but are not limited to, the following groups: phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl, benzofluorenyl, spirobifluorenyl, benzospirobifluorenyl, pyrenyl, fluoranthenyl, Preferably, it has 6 to 35 carbon atoms, preferably 6 to 30 carbon atoms, preferably 6 to 25 carbon atoms, preferably 6 to 20 carbon atoms.

[0040] The heteroaryl group of the present invention refers to a monovalent group in which at least one carbon atom in the aromatic group is replaced by a heteroatom. The heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. Examples of the heteroaryl group include, but are not limited to, the following groups: oxazolyl, benzoxazolyl, naphthoxazolyl, phenanthroxazolyl, anthraxazolyl, tribenzoxazolyl, pyridoxazolyl, pyrimidoxazolyl, triazinexazolyl, quinolinexazolyl, isoquinolinexazolyl, quinazolinoxazolyl, quinoxalinoxazolyl, naphthoxazolyl, thiazolyl, benzothiazolyl, naphthothiazolyl, phenanthrothiazolyl, anthraxazolyl, tribenzothiazolyl, pyridothiazolyl, pyrimidothiazolyl, triazinethiazolyl, quinolinethiazolyl, isoquinolinethiazolyl, naphthothiazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, The phenylimidazolyl, anthraximidazolyl, tribenzimidazolyl, pyridimidazolyl, pyrimidimidazolyl, triazinimidazolyl, quinolinimidazolyl, isoquinolinimidazolyl, quinoxalinimidazolyl, quinazolinimidazolyl, furyl, benzofuranyl, naphthofuranyl, phenanthrofuranyl, anthraxiranyl, tribenzofuranyl, thienyl, benzothienyl, naphthiophenyl, phenanthrothienyl, anthraxiphenyl, tribenzothienyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, naphthrydinyl, phenanthrolinyl, benzoquinolyl, benzoisoquinolyl and the like, but are not limited thereto. It preferably has 2 to 35 carbon atoms, preferably 2 to 30 carbon atoms, further preferably 2 to 25 carbon atoms, and more preferably 3 to 20 carbon atoms.

[0041] The fused ring group of the alicyclic ring and the aromatic ring of the present invention refers to the general term for a monovalent group after the alicyclic ring and the aromatic ring are fused together and a hydrogen atom is removed. Examples of the fused ring groups of the alicyclic ring and the aromatic ring include, but are not limited to, the groups described below, benzocyclopropane, benzocyclobutane, dihydroindenyl, tetrahydronaphthyl, benzocycloheptane, benzocyclooctane, benzocyclobutenyl, indenyl, dihydronaphthyl, benzocycloheptenyl, etc., but are not limited thereto. The alicyclic ring preferably has 3 to 25 carbon atoms, preferably 3 to 20 carbon atoms, preferably 3 to 15 carbon atoms, more preferably 3 to 10 carbon atoms, more preferably 3 to 8 carbon atoms. The aromatic ring preferably has 6 to 35 carbon atoms, preferably 6 to 30 carbon atoms, preferably 6 to 25 carbon atoms, preferably 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms, more preferably 6 to 10 carbon atoms.

[0042] The fused cyclic group of the alicyclic ring and heteroaromatic ring of the present invention refers to the general term for a monovalent group after alicyclic ring and heteroaromatic ring are fused together and a hydrogen atom is removed. Examples of fused cyclic groups of the alicyclic ring and aromatic ring include, but are not limited to, the groups described below, pyridocyclobutane, pyridocyclopentane, pyridocyclohexane, pyridocycloheptane, pyridocyclooctane, pyridocyclopentenyl, pyridocyclohexenyl, pyrimidocyclopentane, pyrimidocyclohexane, pyrimidocyclopentenyl, pyrimidocyclohexenyl, etc., but are not limited thereto. The alicyclic ring preferably has 3 to 25 carbon atoms, preferably 3 to 20 carbon atoms, preferably 3 to 15 carbon atoms, and more preferably 3 to 10 carbon atoms. The heteroaromatic ring preferably has 2 to 35 carbon atoms, preferably 2 to 30 carbon atoms, preferably 2 to 25 carbon atoms, preferably 2 to 18 carbon atoms, preferably 2 to 12 carbon atoms, more preferably 2 to 10 carbon atoms.

[0043] The arylene group of the present invention refers to a general term for a monovalent group after removing a hydrogen atom from the aromatic carbon of an aromatic compound molecule. The arylene group includes a monocyclic arylene group, a polycyclic arylene group, a condensed ring arylene group or a combination thereof. The arylene group examples include, but are not limited to, the groups described below, phenylene, biphenylene, terphenylene, quaterphenylene, naphthylene, phenanthrylene, anthracene, triphenylene, fluorenylene, benzofluorenylene, naphthylene, spirobifluorenylene, etc., but are not limited thereto. Preferably, it has 6 to 35 carbon atoms, preferably 6 to 30 carbon atoms, preferably 6 to 25 carbon atoms, preferably 6 to 20 carbon atoms, and more preferably 6 to 18 carbon atoms.

[0044] The sub-heteroaryl group refers to a divalent group in which at least one carbon atom in the sub-aryl group is replaced by a heteroatom. The heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. The sub-heteroaryl group includes a monocyclic sub-heteroaryl group, a polycyclic sub-heteroaryl group, a condensed ring sub-heteroaryl group, or a combination thereof. The sub-heteroaryl group examples include, but are not limited to, the groups described below, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, etc., but are not limited thereto. Preferably, it has 2 to 35 carbon atoms, preferably 2 to 30 carbon atoms, preferably 2 to 25 carbon atoms, preferably 2 to 20 carbon atoms.

[0045] The sub-fused cyclic radical of the alicyclic ring and the aromatic ring of the present invention refers to the general term for the alicyclic ring and the aromatic ring after two hydrogen atoms are removed after the alicyclic ring is fused together, and the remaining divalent group. Examples of the sub-fused cyclic radical of the alicyclic ring and the aromatic ring include, but are not limited to, the groups described below, benzocyclopropene, benzocyclobutene, indenyl, tetrahydronaphthyl, benzocycloheptyl, benzocyclobutene, indenyl, dihydronaphthyl, naphthylene, naphthylene, naphthylene, naphthylene, naphthylene, etc., but are not limited thereto. The alicyclic ring preferably has 3 to 25 carbon atoms, preferably 3 to 20 carbon atoms, preferably 3 to 15 carbon atoms, and more preferably 3 to 8 carbon atoms. The aromatic ring preferably has 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, preferably 6 to 18 carbon atoms, preferably 6 to 10 carbon atoms.

[0046] The sub-fused cyclic group of the alicyclic ring and heteroaromatic ring of the present invention refers to the general term for the alicyclic ring and the heteroaromatic ring after two hydrogen atoms are removed after the alicyclic ring is fused together, and the remaining divalent group. Examples of the sub-fused cyclic groups of the alicyclic ring and the heteroaromatic ring include, but are not limited to, the groups described below, sub-pyridocyclopropane, sub-pyridocyclobutane, sub-pyridocyclopentane, sub-pyridocyclohexane, sub-pyridocyclopentenyl, sub-pyridocyclohexenyl, etc., but are not limited thereto. The alicyclic ring preferably has 3 to 25 carbon atoms, preferably 3 to 20 carbon atoms, preferably 3 to 15 carbon atoms, and more preferably 3 to 8 carbon atoms. The heteroaromatic ring preferably has 2 to 35 carbon atoms, preferably 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, preferably 2 to 18 carbon atoms, preferably 2 to 10 carbon atoms.

[0047] The alicyclic ring of the present invention includes cycloalkyl, cycloalkenyl, cycloalkynyl, etc. Examples of the alicyclic ring include, but are not limited to, the following groups, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, etc. Preferably, it has 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, preferably 5 to 10 carbon atoms, and most preferably 5 to 7 carbon atoms.

[0048] The alicyclic group of the present invention refers to a divalent group formed by removing a hydrogen atom from an alicyclic hydrocarbon molecule, wherein the heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. Examples of the alicyclic group include, but are not limited to, the following groups, furanyl, tetrahydrofuranyl, thienyl, tetrahydrothienyl, piperidinyl, pyrrolidinyl, tetrahydropyranyl, etc. Preferably, the alicyclic group has 2 to 20 carbon atoms, preferably 2 to 20 carbon atoms, more preferably 2 to 15 carbon atoms, more preferably 2 to 10 carbon atoms, and most preferably 2 to 6 carbon atoms.

[0049] The present invention provides an imidazole compound having a general structural formula as shown in Formula 1,

[0050]

[0051] Wherein, Ar is selected from the following groups,

[0052]

[0053] The A's are the same or different and are selected from C(Ra) or N, and the Ra's are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C35 aryl, substituted or unsubstituted C2-C35 heteroaryl, substituted or unsubstituted C3-C25 alicyclic and C6-C35 aromatic ring fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C35 heteroaromatic ring fused ring group, substituted or unsubstituted C3-C25 alicyclic heterocyclic group, and at least two adjacent Ra's are bonded to each other to form a substituted or unsubstituted ring;

[0054] The R 0 One selected from substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C35 aryl, substituted or unsubstituted C2-C35 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C6-C35 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C35 heteroaromatic ring, and a substituted or unsubstituted C3-C25 alicyclic heterocyclic group;

[0055] The R 1 One selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C35 aryl, substituted or unsubstituted C2-C35 heteroaryl, substituted or unsubstituted C3-C25 alicyclic and C6-C35 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C35 heteroaromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic heterocyclic group;

[0056] The A 1 , A 2 are independently selected from the groups shown below,

[0057]

[0058] The Bs are the same or different and are selected from C(Rb) or N, and the Rb are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C35 aryl, substituted or unsubstituted C2-C35 heteroaryl, substituted or unsubstituted C3-C25 alicyclic and C6-C35 aromatic ring fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C35 heteroaromatic ring fused ring group, substituted or unsubstituted C3-C25 alicyclic heterocyclic group, or two adjacent Rb are bonded to each other to form a substituted or unsubstituted ring;

[0059] The X 0 is selected from O or S; said E is selected from N or C(Re);

[0060] The Re, R 2 One independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C35 aryl, substituted or unsubstituted C2-C35 heteroaryl, substituted or unsubstituted C3-C25 alicyclic and C6-C35 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C35 heteroaromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic heterocyclic group;

[0061] The X are the same or different and are selected from C(Rx) or N, the R x One selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C35 aryl, substituted or unsubstituted C2-C35 heteroaryl, substituted or unsubstituted C3-C25 alicyclic and C6-C35 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C35 heteroaromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic heterocyclic group;

[0062] The L a , L b , L 1 , L 2The substituents are independently selected from a single bond, a substituted or unsubstituted C6-C35 arylene group, a substituted or unsubstituted C2-C35 heteroarylene group, a substituted or unsubstituted C3-C25 alicyclic and C6-C35 aromatic ring sub-condensed ring group, a substituted or unsubstituted C3-C25 alicyclic and C2-C35 heteroaromatic ring sub-condensed ring group, or a combination thereof; the substituents in the "substituted or unsubstituted" group are selected from the following groups: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 alicyclic heterocyclic group, or two adjacent substituents are bonded to each other to form a substituted or unsubstituted ring.

[0063] Preferably, the imidazole compound of formula 1 is selected from at least one of the structures shown below:

[0064]

[0065] Preferably, the X are the same or different and are selected from C(Rx) or N, and the R x One selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring group, a substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaromatic fused ring group, a substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaromatic fused ring group, a substituted or unsubstituted C3-C20 alicyclic heterocyclic group.

[0066] Preferably, the X are the same or different and are selected from C(Rx) or N, and the R x One selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C15 alicyclic ring and a C6-C25 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C15 alicyclic ring and a C2-C25 heteroaromatic ring, and a substituted or unsubstituted C3-C15 alicyclic heterocyclic group.

[0067] Preferably, the X are the same or different and are selected from C(Rx) or N, and the R xselected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted The invention can be selected from the group consisting of substituted phenanthryl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted dihydroindanyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indenyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, and substituted or unsubstituted isoquinolyl.

[0068] Preferably, Ar is selected from one of the following groups:

[0069]

[0070]

[0071] The Ys are the same or different and are selected from C(Ry) or N, and the Rys are the same or different and are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaromatic fused ring, substituted or unsubstituted C3-C20 alicyclic heterocyclic, or two adjacent Rys are bonded to each other to form a substituted or unsubstituted ring;

[0072] The R 0 One selected from substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring group, a substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaromatic fused ring group, a substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaromatic fused ring group, a substituted or unsubstituted C3-C20 alicyclic heterocyclic group;

[0073] The R 1One selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring group, a substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaromatic fused ring group, a substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaromatic fused ring group, a substituted or unsubstituted C3-C20 alicyclic heterocyclic group.

[0074] Preferably, Ar is selected from one of the following groups:

[0075]

[0076]

[0077]

[0078] The c1 is selected from 0, 1, 2, 3, 4; the c2 is selected from 0, 1, 2; the c3 is selected from 0, 1, 2, 3;

[0079] The Ry's are the same or different and are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic fused ring, substituted or unsubstituted C3-C15 alicyclic and C2-C25 heteroaromatic fused ring, substituted or unsubstituted C3-C15 alicyclic heterocyclic, or two adjacent Ry's are bonded to each other to form a substituted or unsubstituted ring;

[0080] The R 0 One selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C15 alicyclic ring and a C6-C25 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C15 alicyclic ring and a C2-C25 heteroaromatic ring, and a substituted or unsubstituted C3-C15 alicyclic heterocyclic group;

[0081] The R 1One selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C15 alicyclic ring and a C6-C25 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C15 alicyclic ring and a C2-C25 heteroaromatic ring, and a substituted or unsubstituted C3-C15 alicyclic heterocyclic group.

[0082] Preferably, the Ry are the same or different and are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl. , substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted dihydroindenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indenyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, or two adjacent Ry are bonded to each other to form a substituted or unsubstituted ring;

[0083] The R 0is selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted dihydroindenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indenyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted phenanthridinyl, substituted or unsubstituted phenanthroline;

[0084] The R 1selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted diphenyl The invention may be selected from the group consisting of substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted dihydroindenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indenyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted phenanthridinyl and substituted or unsubstituted phenanthroline.

[0085] Preferably, the A 1 , A 2 Independently selected from one of the groups shown below,

[0086]

[0087] The Bs are the same or different and are selected from C(Rb) or N, and the Rb are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaromatic fused ring, substituted or unsubstituted C3-C20 alicyclic heterocyclic, or two adjacent Rb are bonded to each other to form a substituted or unsubstituted ring;

[0088] The X 0 is selected from O or S; said E is selected from N or C(Re);

[0089] The Re, R2 It is independently selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C20 alicyclic ring and a C2-C30 heteroaromatic ring, and a substituted or unsubstituted C3-C20 alicyclic heterocyclic group.

[0090] Preferably, the A 1 , A 2 Independently selected from one of the groups shown below,

[0091]

[0092]

[0093]

[0094] The d1 is selected from 0, 1, 2, 3, 4; the d2 is selected from 0, 1, 2; the d3 is selected from 0, 1, 2, 3;

[0095] The Rb's are the same or different and are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic ring fused ring group, substituted or unsubstituted C3-C15 alicyclic and C2-C25 heteroaromatic ring fused ring group, substituted or unsubstituted C3-C15 alicyclic heterocyclic group, or two adjacent Rb's are bonded to each other to form a substituted or unsubstituted ring;

[0096] The X 0 is selected from O or S; said E is selected from N or C(Re);

[0097] The Re, R 2 It is independently selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C15 alicyclic ring and a C6-C25 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C15 alicyclic ring and a C2-C25 heteroaromatic ring, and a substituted or unsubstituted C3-C15 alicyclic heterocyclic group.

[0098] Preferably, the Rb are the same or different and are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, One of substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted dihydroindanyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indenyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, or two adjacent Rb are bonded to each other to form a substituted or unsubstituted ring;

[0099] The Re, R 2 and independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted diphenylene, substituted or unsubstituted terphenylene ... fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted diphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted terphenylene The invention can be selected from the group consisting of benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted dihydroindanyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indenyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted phenanthridinyl and substituted or unsubstituted phenanthroline.

[0100] Preferably, the L a , L b Independently selected from a single bond or one of the groups shown below,

[0101]

[0102] The Zs are the same or different and are selected from C(Rz) or N, and the Rzs are the same or different and are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 alicyclic group, or two adjacent Rzs are bonded to each other to form a substituted or unsubstituted ring;

[0103] a0 is selected from 0, 1, 2, 3, 4, 5, 6; R 3 the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 alicyclic group, or two adjacent R 3 They are bonded to each other to form a substituted or unsubstituted ring.

[0104] Preferably, the L a , L b Independently selected from a single bond or one of the groups shown below,

[0105]

[0106]

[0107] a0 is selected from 0, 1, 2, 3, 4, 5, 6; a1 is selected from 0, 1, 2, 3, 4; a2 is selected from 0, 1, 2, 3; a3 is selected from 0, 1, 2; a4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8;

[0108] The Rz are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 alicyclic group;

[0109] The R 3 The same or different ones are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 alicyclic group;

[0110] The R 4The same or different ones are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C20 alicyclic and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C20 alicyclic and a C2-C30 heteroaromatic ring, and a substituted or unsubstituted C3-C20 alicyclic heterocyclic group.

[0111] Preferably, the Rz are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl;

[0112] The R 3 the same or different being selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl;

[0113] The R 4 The same or different radicals are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted indanyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indenyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted pyridinyl and substituted or unsubstituted pyrimidinyl.

[0114] Preferably, the L 1 , L 2 Independently selected from a single bond or one of the groups shown below,

[0115]

[0116] The V's are the same or different and are selected from C(Rv) or N, the Rv's are the same or different and are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 heterocyclic group, or two adjacent Rv's are bonded to each other to form a substituted or unsubstituted ring.

[0117] Preferably, the L 1 , L 2 Independently selected from a single bond or one of the groups shown below,

[0118]

[0119] b1 is selected from 0, 1, 2, 3, 4; b2 is selected from 0, 1, 2, 3; b3 is selected from 0, 1, 2; b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8; b5 is selected from 0, 1, 2, 3, 4, 5, 6; b6 is selected from 0, 1, 2, 3, 4, 5;

[0120] The Rvs are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, and substituted or unsubstituted C3-C20 alicyclic group;

[0121] The R 5 The same or different ones are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C20 alicyclic and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C20 alicyclic and a C2-C30 heteroaromatic ring, and a substituted or unsubstituted C3-C20 alicyclic heterocyclic group.

[0122] Preferably, the R v the same or different being selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl;

[0123] The R 5The same or different radicals are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted indanyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indenyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted pyridinyl and substituted or unsubstituted pyrimidinyl.

[0124] Preferably, the imidazole compound of formula 1 is selected from at least one of the structures shown below:

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143] Some specific chemical structures of the imidazole compounds of Formula 1 of the present invention are listed above, but the present invention is not limited to these listed chemical structures, and all groups based on the structure shown in Formula 1 and having substituents as defined above should be included.

[0144] The present invention also provides an organic electroluminescent device, which contains the imidazole compound of the present invention.

[0145] Preferably, the organic electroluminescent device includes an anode, a cathode, and at least one of an organic layer or a covering layer, wherein the organic layer is located between the anode and the cathode, and the covering layer is located on the outside of the cathode or the anode, and at least one of the organic layer or the covering layer contains the above-mentioned imidazole compound of the present invention.

[0146] Preferably, the organic electroluminescent device comprises an anode, a cathode and an organic layer, wherein the organic layer is located between the anode and the cathode, and the organic layer contains the imidazole compound of the present invention.

[0147] Preferably, the organic layer includes at least one of a light-emitting layer and an electron transport region, and at least one of the light-emitting layer and the electron transport region contains the imidazole compound of the present invention.

[0148] Preferably, the organic layer includes a light-emitting layer, and the light-emitting layer contains the imidazole compound of the present invention.

[0149] Preferably, the light-emitting layer includes a host material and a doping material, and the host material contains the imidazole compound of the present invention.

[0150] Preferably, the organic layer includes an electron transport region, and the electron transport region contains the imidazole compound of the present invention.

[0151] Preferably, the electron transport region includes at least one of a hole blocking layer, an electron transport layer, and an electron injection layer, and at least one of the hole blocking layer, the electron transport layer, and the electron injection layer contains the imidazole compound of the present invention.

[0152] Preferably, the electron transport region includes an electron transport layer, and the electron transport layer contains the imidazole compound of the present invention.

[0153] Preferably, the organic electroluminescent device comprises an anode, a cathode and a covering layer, wherein the covering layer is located outside the cathode or the anode, and the covering layer contains the above-mentioned imidazole compound of the present invention.

[0154] The functional layer of the organic electroluminescent device of the present invention may contain at least one of the following functional layers: hole injection layer, hole transport layer, luminescence auxiliary layer, electron blocking layer, luminescent layer, hole blocking layer, electron transport layer, electron injection layer, covering layer, etc. All functional layers with hole injection and / or transport properties, electron injection and / or transport properties, luminescent properties, or light extraction properties should be included. Each functional layer may be composed of a single-layer thin film or a multi-layer thin film, and each thin film may be composed of only one material or a plurality of materials.

[0155] The present invention has no particular limitation on the materials of the thin films in the organic electroluminescent device, and materials known in the art can be used. The organic functional layers of the organic electroluminescent device mentioned above and the electrodes on both sides of the device are introduced below:

[0156] The anode of the present invention needs good electrical conductivity, good chemical and morphological stability, and the work function needs to match the HOMO energy level of the hole injection material. The anode includes but is not limited to the following materials, metal oxides, combinations of metals and oxides, metals or their alloys, laminated materials, etc. Specific examples may include indium tin oxide (ITO), zinc oxide (ZnO), aluminum zinc oxide (AZO), silver (Ag), aluminum (Al), nickel (Ni), gold (Au), platinum (Pt), chromium (Cr), copper (Cu), palladium (Pd), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), etc., but are not limited thereto.

[0157] The cathode of the present invention needs to have a smaller work function, and the work function should match the LUMO energy level of the electron injection material. The cathode includes but is not limited to the following materials, metals or their alloys, laminated materials, etc. Specific examples may include aluminum (Al), magnesium (Mg), silver (Ag), calcium (Ca), indium (In), ytterbium (Yb), magnesium:silver (Mg:Ag), magnesium silver (Mg:Al), etc., but are not limited thereto.

[0158] The hole injection material of the present invention can increase the hole injection between interfaces and improve the performance of the device. The hole injection layer includes but is not limited to the following materials, aromatic amine derivatives, metal oxides, phthalocyanine metal complexes, polycyano conjugated organics, polymers, etc. Specific examples may include N, N'-bis [4-di (m-tolyl) aminophenyl] -N, N'-diphenylbenzidine (DNTPD), 4,4',4"-tri (N- (1-naphthyl) -N-phenylamino) triphenylamine (1-TNATA), 4,4',4"-tri (N, N-2-naphthylphenylamino) triphenylamine (2-TNATA), tungsten trioxide (WO 3 ), molybdenum oxide (MoO 3), zinc phthalocyanine (ZnPc), 1,4,5,8,9,11-hexaazabenzonitrile (HAT-CN), (2E,2'E,2'E)-2,2',2'-(cyclopropane-1,2,3-triimide)tris(2-(2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)phenyl)acetonitrile), (2E,2'E,2'E)-2,2',2'-(cyclopropane-1,2,3-trimethylene)tris(2-(perfluorophenyl)acetonitrile), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly(4-vinyltriphenylamine) (PVTPA), etc., but are not limited to these.

[0159] The hole transport material of the present invention needs to have a high hole mobility, a high heat stability, and a naturally formed good thin film state without pinhole defects. The hole transport layer includes but is not limited to the following materials, aromatic amine derivatives, carbazole derivatives, polymers, etc. Specific examples may include 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), N,N,N',N'-tetra-1-naphthyl[1,1'-biphenyl]-4,4'-diamine (α-TNB), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di(2-naphthyl)-1,1'-biphenyl-4,4'-diamine (β-NPB), N-(1,1'-biphenyl )-2-yl-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobifluorene-2-amine, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), 1,3,5-tri(9-carbazolyl)benzene (TCB), 4,4',4"-tri(carbazolyl-9-yl)triphenylamine (TCTA), polysilane (PMPS), etc., but are not limited thereto.

[0160] The electron blocking material of the present invention needs to have good hole transporting ability and electron blocking ability, so as to block the electrons in the light-emitting layer. The electron blocking layer includes but is not limited to the following materials, aromatic amine derivatives, carbazole derivatives, etc. Specific examples may include N,N-di([1,1'-biphenyl]-4-yl)-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine, N-(4'-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine, N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPD), N-(1,1'-biphenyl)-2-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobifluorene-4-amine, etc., but are not limited thereto.

[0161] The light-emitting layer of the present invention comprises a main material and a doping material, and the light-emitting material can be a blue light-emitting material, a red light-emitting material, a green light-emitting material or a combination thereof. The doping ratio of the main material and the doping material can be different according to the materials used, and the doping ratio of the doping material is usually 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%.

[0162] The host material of the light-emitting layer not only needs to have bipolar charge transport properties, but also needs to have an appropriate energy level to effectively transfer the excitation energy to the guest light-emitting material. The host material can be one material or two or more materials. The main material includes but is not limited to the following materials, aromatic amine compounds, fused aromatic ring derivatives, metal complexes, silicon-containing compounds, bicarbazole compounds, biphenylcarbazole compounds, binaphthylcarbazole compounds, indolecarbazole compounds, indolebenzocarbazole compounds, indenylcarbazole compounds, benzofurancarbazole compounds, benzothiophenecarbazole compounds, carbazole compounds, furan compounds, thiophene compounds, oxazole compounds, thiazole compounds, imidazole compounds and other heterocyclic compounds, etc. Specific examples may include 3,3'-bis(N-carbazole)-1,1'-biphenyl (MCBP), 9-(4-(10-phenylanthracene-9-yl)phenyl)-9H-carbazole (CzPA), 4,4'-bis(carbazole-9-yl)-2,2'-dimethylbiphenyl (CDBP), 1,3-bis( N-carbazolyl)benzene (MCP), 9,9-dimethyl-N,N-diphenyl-7-(4-(1-phenyl-1H benzo[d]imidazol-2-yl)phenyl)-9H-fluoren-2-amine (EFIN), 10-(4'-(diphenylamino)biphenyl-4-yl)acridin-9(10H)-one (ADBP), tris[4-(pyrenyl)-phenyl]amine (TPyPA), 9,10-di(2-naphthyl)- 1-(7-[9,9'-bianthracene]-10-yl-9,9-dioctyl-9H-fluorene-2-yl)pyrene (BAnF8Pye), 9,9,9',9'-tetrakis(4-methylphenyl)-2,2'-bi-9H-fluorene (BDAF), tris(6-fluoro-8-hydroxyquinoline)aluminum (6FAlq 3 ), tris(8-hydroxyquinoline)aluminum (Alq 3 ), bis(10-hydroxybenzo[H]quinolinolato)beryllium (BeBq 2 ), bis(8-hydroxyquinoline)zinc (Znq 2), 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (BCzPh), 9,9'-di([1,1'-biphenyl]-4-yl)-9H,9'H-3,3'-bicarbazole, 9,9'-di([1,1'-biphenyl]-3-yl)-9H,9'H-3,3'-bicarbazole, 9,9'-di([1,1'-biphenyl]-2-yl)-9H,9'H-3,3'-bicarbazole, 9-([1,1'-biphenyl]-4-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole, 9-([1,1'-biphenyl]-3-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole, 9-([1,1'-biphenyl]-2-yl)-9 '-phenyl-9H,9'H-3,3'-bicarbazole, 9,9'-di([1,1':4',1'-triphenyl]-4-yl)-9H,9'H-3,3'-bicarbazole, 9,9'-di(naphthalene-1-yl)-9H,9'H-3,3'-bicarbazole, 9,9'-di(naphthalene-2-yl)-9H,9'H-3,3'-bicarbazole, 9,9'-biphenyl-9H,9'H-3,3'-bicarbazole-6-carbonitrile (BCzSCN), 5,7-diphenyl-5,7-dihydroindole[2,3-b]carbazole, 5,7-di(1,1'-biphenyl-4-yl)-5,7-dihydroindole[2,3-b]carbazole, 5,7-di(1,1'-biphenyl-3-yl)-5 ,7-dihydroindole[2,3-b]carbazole, 5,7-bis(1,1'-biphenyl-2-yl)-5,7-dihydroindole[2,3-b]carbazole, 5-(1,1'-biphenyl-4-yl)-7-phenyl-5,7-dihydroindole[2,3-b]carbazole, 5-(1,1'-biphenyl-3-yl)-7-phenyl-5,7-dihydroindole[2,3-b]carbazole, 5-(1,1'-biphenyl-2-yl)-7-phenyl-5,7-dihydroindole[2,3-b]carbazole, 5,7-bis(1,1:4,1-triphenyl-4-yl)-5,7-dihydroindole[2,3-b]carbazole, 5,7-dinaphth-1-yl-5,7-dihydroindole[2,3-b]carbazole , 5,7-dinaphth-2-yl-5,7-dihydroindole[2,3-b]carbazole, 5,11-diphenyl-5,11-dihydroindole[3,2-b]carbazole, 5,11-bis(1,1'-biphenyl-4-yl)-5,11-dihydroindole[3,2-b]carbazole, 5-(1,1'-biphenyl-4-yl)-11-phenyl-5,11-dihydroindole[3,2-b]carbazole, 5,11-dinaphth-1-yl-5,11-dihydroindole[3,2-b]carbazole, 5,11-bis(4-(naphthyl)phenyl)-5,11-dihydroindole[3,2-b]carbazole, 5-(1,1:4,1-triphenyl-4-yl)-7-phenyl-5,7-dihydroindole[2,3-b] carbazole, etc., but not limited thereto. The imidazole compound of formula 1 of the present invention is preferred. The imidazole compound of formula 1 of the present invention can be used as a main body material alone or in combination with a p-type main body material. When used in combination with a p-type main body material, the weight ratio of the imidazole compound of formula 1 of the present invention to the p-type main body material is 1:99 to 99:1, preferably 20:80 to 80:20. ,

[0163] The doping material may be a fluorescent material, a phosphorescent material, a TADF material or a combination thereof. The doping material includes but is not limited to the following materials, metal complexes, aromatic amine derivatives, styrylamine compounds, fused aromatic compounds, heterocyclic compounds, etc. Specific examples may include bis[4-tert-butyl-2',6'-difluoro-2,3'-bipyridine](acetylacetonate)iridium (FK306), bis(2-(2-hydroxyphenyl)-pyridine)beryllium (Bepp 2 ), bis(3,4,5-trifluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium (Ir(tfpd) 2 pic), bis(2-(naphthalene-2-yl)pyridine)(acetylacetonate)iridium(Ir(npy) 2 acac), tris[2-phenyl-4-methylquinoline)]iridium (Ir(Mphq) 3 ), bis(2-phenylpyridinium) acetylacetonate (Ir(ppy) 2 (acac)), tris(2-(3-p-xylyl)pyridine iridium (TEG), bis(2-phenylpyridine)[2-(biphenyl-3-yl)pyridine]iridium (Ir(ppy) 2 (m-bppy)), bis[2-(3,5-dimethylphenyl)-4-methylquinolinol](acetylacetonate)iridium (Ir(mphmq) 2 acac), bis(1-phenyl-isoquinoline)(acetylacetonate)iridium(Ir(piq) 2 (acac)), tris[5-hexyl-2-(1-isoquinolyl)phenyl]iridium (Hex-Ir(piq) 3), platinum octaethylporphyrin (PtOEP), 4,4'-[1,4-phenylene di-(1E)-2,1-ethylenediyl]bis[N,N-diphenylaniline] (DSA-Ph), N-phenyl-4-(9-phenyl-9H-aminoazol-3-yl)-N-(4-(10-phenylanthracen-9-yl)phenyl)aniline (PCBAPA), N,N,N',N'-tetrakis(4-methyl phenyl)-[9,9'-bianthracene]-10,10'-diamine (BA-TTB), 1,1'-bis(3,5-bis(trifluoromethyl)phenyl)-9,9'-bianthracene (Ban-(3,5)-CF3), 2,5,8,11-tetra-tert-butylperylene (TBPe), N1,N6-bis(dibenzofuran-4-yl)-N1,N6-di-m-tolylpyrene-1,6-diamine, red fluorescent olefins, 9-(9-phenylcarbazole-3-yl)-10-(naphthalene-1-yl) (PCAN), 1,4-bis(4-(9H-carbazole-9-yl)phenylvinyl)benzene (BCzSB), 1,1'-(4,4'-(4-phenyl-4H-1,2,4-triazole-3,5-diyl)bis(4,1-phenylene))bis(1H-phenoxazine) (2PXZ-TAZ), 2,5- Bis(4-(1H-benzoxazin-1-yl)phenyl)-1,3,4-oxadiazole (2PXZ-OXD), (E)-2-(2-tert-butyl-6-(2-(2,6,6-trimethyl-2,4,5,6-tetrahydro-1H-pyrrolo[3,2,1-IJ]]quinolin-8-yl)vinyl)-4H-pyran-4-ylidene)malononitrile (DCQTB), etc., but are not limited thereto.

[0164] The hole blocking material of the present invention needs to have good hole blocking ability so as to block holes in the light-emitting layer. The hole blocking layer material includes but is not limited to the following materials, metal complexes, heteroaromatic compounds, etc. Specific examples may include di(2-methyl-8-hydroxyquinoline-N1,08)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 2,9-di(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 1,3,5-tri(N-phenyl-2-benzimidazole)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), etc., but are not limited thereto.

[0165] The electron transport material of the present invention needs to have good electron mobility, suitable LUMO and HOMO values, high glass transition temperature and thermal stability, the ability to form non-crystalline thin films, etc. The electron transport layer includes but is not limited to the following materials, heteroaromatic compounds, metal complexes, polymers, etc. Specific examples may include 2,9-di(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 2-(9,9'-spirofluorene-2-yl)-4,6-di(1,1:3,1-terphenyl)-5-yl)-1,3,5-triazine, 2,5-di-(4-naphthyl)-1,3,4-oxadiazole (BND), 1,3,5-tri(N-phenyl-2-benzimidazole)benzene (TPBi), 8-hydroxyquinoline aluminum (Alq 3 ), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), bis(8-hydroxyquinoline)zinc(II) (Znq), poly[9,9-bis[6'-(N,N,N-trimethylammonium)hexyl]fluorene-alt-co-1,4-phenylene]bromide (FPQ-Br), etc., but not limited thereto. The imidazole compound of formula 1 of the present invention is preferred.

[0166] The electron injection material of the present invention can increase the electron injection between interfaces and improve the performance of the device. The electron injection layer material includes but is not limited to the following materials, metals, metal compounds, metal oxides, etc. Specific examples may include lithium fluoride (LiF), 8-hydroxyquinoline lithium (Liq), sodium fluoride (NaF), potassium acetate (CH 3 COOK), potassium silicate (K 2 SiO 3 ), lithium oxide (Li 2 O) etc., but not limited thereto.

[0167] The cover layer material of the present invention has the function of improving the light extraction efficiency of the device. The cover layer material includes but is not limited to the following materials, metal compounds, aromatic amine derivatives, carbazole derivatives, etc. Specific examples may include 8-hydroxyquinoline aluminum (Alq 3 ), N,N'-di(naphthalene-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (α-NPD), N4,N4,N4',N4'-tetrakis(4-methoxyphenyl)-[1,1'-biphenyl]-4,4'-diamine (MeO-TPD), etc. The imidazole compound of formula 1 of the present invention is preferred.

[0168] There is no particular restriction on the method for preparing each thin film in the organic electroluminescent device of the present invention, and sputtering, metal organic chemical vapor deposition, sol-gel, pulsed laser deposition, spray pyrolysis, evaporation, etc. may be used, but are not limited thereto.

[0169] The organic electroluminescent device of the present invention is mainly used in the field of information display technology and the field of lighting. In terms of information display, it is widely used in various information displays, such as mobile phones, tablet computers, flat-screen TVs, smart watches, VR, vehicle-mounted systems, digital cameras, wearable devices, etc.

[0170] Synthesis Example

[0171] There is no particular limitation on the preparation method of the imidazole compound represented by Formula 1 of the present invention, and conventional methods known to those skilled in the art can be used, such as carbon-carbon coupling reaction, etc. The imidazole compound represented by Formula 1 of the present invention can be prepared by, for example, the synthetic route shown below.

[0172]

[0173] The Xn is a halogen, for example, Xn are the same or different and are selected from Cl, Br, and I.

[0174] In addition, the order of the above reactions can also be changed to obtain the imidazole compound represented by Formula 1 of the present invention.

[0175] Raw materials and reagents: The present invention has no particular restrictions on the raw materials or reagents used in the following synthetic examples, and they can be commercially available products or prepared by preparation methods well known to those skilled in the art. The raw materials and reagents used in the present invention are all reagent-grade.

[0176] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters, UK); Vario ELcube organic element analyzer (Elementar, Germany).

[0177] Synthesis Example 1: Preparation of Compound 4

[0178]

[0179] Synthesis of intermediate A-4:

[0180] Under nitrogen protection, a-4 (50.01 g, 185.00 mmol), biboric acid pinacol ester (103.35 g, 407.00 mmol), KOAc (47.21 g, 481.00 mmol), Pd(dppf)Cl were added to the reaction bottle. 2 (812 mg, 1.11 mmol), 1.2 L THF, react under reflux for 6.5 hours. After the reaction is completed, cool to room temperature, add water, filter to obtain a filter cake, and dry in a vacuum oven. The crude product is separated and purified by silica gel column (n-hexane: ethyl acetate = 5:4) to obtain intermediate A-4 (53.27 g, 79%); HPLC purity ≥ 99.71%.

[0181] Synthesis of intermediate B-4:

[0182] Under nitrogen protection, A-4 (52.05 g, 142.80 mmol), b-4 (76.75 g, 280.00 mmol), Na 2 CO 3 (41.55 g, 392.00 mmol), Pd(PPh 3 ) 4 (3.24 g, 2.80 mmol), 1 L 1,4-dioxane, react under reflux for 7.5 hours. After the reaction is completed, cool to room temperature, add water, extract with dichloromethane, and the organic layer is washed with anhydrous MgSO 4 After drying, the solvent was removed under reduced pressure and recrystallized with toluene / petroleum ether = 5:1 to obtain intermediate B-4 (53.09 g, 76%); HPLC purity ≥ 99.80%.

[0183] Synthesis of intermediate C-4:

[0184] Under nitrogen protection, add B-4 (49.90 g, 100.00 mmol), biboric acid pinacol ester (27.93 g, 110.00 mmol), K 2 CO 3 (17.97g,130.00mmol), Pd(dppf)Cl 2 (0.37 g, 0.50 mmol), 850 ml THF, react under reflux for 7 hours. After the reaction is completed, cool to room temperature, add water, filter to obtain a filter cake, and recrystallize with toluene / n-hexane = 6:1 to obtain intermediate C-4 (45.47 g, 77%); HPLC purity ≥ 99.87%.

[0185] Synthesis of compound 4:

[0186] Under nitrogen protection, C-4 (22.73 g, 38.50 mmol), c-4 (11.31 g, 35.00 mmol), K 2 CO 3 (7.26 g, 52.5 mmol), Pd(OAc) 2 (144 mg, 0.70 mmol), P(t-Bu) 3 (141 mg, 0.70 mmol), 300 ml THF, react under reflux for 9 hours. After the reaction, cool to room temperature, add water, extract with dichloromethane, and the organic layer is washed with anhydrous MgSO 4Dry, remove the solvent under reduced pressure, and recrystallize from toluene to obtain compound 4 (17.32 g, 70%); HPLC purity ≥ 99.93%. Mass spectrum m / z: 706.2380 (theoretical value: 706.2369). Theoretical element content (%) C 49 H 30 N 4 O 2 :C, 83.27;H, 4.28;N, 7.93. Measured element content (%): C, 83.30;H, 4.24;N, 7.98.

[0187] Synthesis Example 2: Preparation of Compound 10

[0188]

[0189] According to the same preparation method as compound 4 in Synthesis Example 1, b-4 was replaced by an equal mole of b-10, and c-4 was replaced by an equal mole of c-10 to obtain compound 10 (20.64 g). The solid purity detected by HPLC was ≥99.91%. Mass spectrum m / z: 906.2980 (theoretical value: 906.2995). Theoretical element content (%) C 65 H 38 N 4 O 2 :C, 86.07;H, 4.22;N, 6.18. Measured element content (%): C, 86.10;H, 4.18;N, 6.23.

[0190] Synthesis Example 3: Preparation of Compound 23

[0191]

[0192] According to the same preparation method as compound 4 in Synthesis Example 1, b-4 was replaced by an equal mole of b-23, and c-4 was replaced by an equal mole of c-10 to obtain compound 23 (19.97 g). The solid purity detected by HPLC was ≥99.96%. Mass spectrum m / z: 838.2239 (theoretical value: 838.2225). Theoretical element content (%) C 57 H 34 N 4 S 2 :C, 81.60;H, 4.08;N, 6.68. Measured element content (%): C, 81.65;H, 4.04;N, 6.71.

[0193] Synthesis Example 4: Preparation of Compound 30

[0194]

[0195] According to the same preparation method as compound 4 in Synthesis Example 1, b-4 was replaced by an equal mole of b-30, and c-4 was replaced by an equal mole of c-30 to obtain compound 30 (17.44 g). The solid purity detected by HPLC was ≥99.94%. Mass spectrum m / z: 755.2586 (theoretical value: 755.2573). Theoretical element content (%) C 54 H 33 N 3 O 2 :C, 85.81;H, 4.40;N, 5.56. Measured element content (%): C, 85.85;H, 4.37;N, 5.60.

[0196] Synthesis Example 5: Preparation of Compound 49

[0197]

[0198] According to the same preparation method as compound 4 in Synthesis Example 1, b-4 was replaced by an equal mole of b-49, and c-4 was replaced by an equal mole of c-49 to obtain compound 49 (17.46 g). The solid purity detected by HPLC was ≥99.97%. Mass spectrum m / z: 792.1889 (theoretical value: 792.1878). Theoretical element content (%) C 49 H 28 N 8 S 2 :C, 74.22;H, 3.56;N, 14.13. Measured element content (%): C, 74.27;H, 3.52;N, 14.16.

[0199] Synthesis Example 6: Preparation of Compound 96

[0200]

[0201] According to the same preparation method as compound 4 in Synthesis Example 1, b-4 was replaced by an equal mole of b-96, and c-4 was replaced by an equal mole of c-96 to obtain compound 96 (21.55 g). The solid purity detected by HPLC was ≥99.92%. Mass spectrum m / z: 832.2852 (theoretical value: 832.2838). Theoretical element content (%) C 59 H 36 N 4 O 2 :C, 85.08;H, 4.36;N, 6.73. Measured element content (%): C, 85.12;H, 4.31;N, 6.77.

[0202] Synthesis Example 7: Preparation of Compound 102

[0203]

[0204] According to the same preparation method as compound 4 in Synthesis Example 1, b-4 was replaced by an equal mole of b-102, and c-4 was replaced by an equal mole of c-96 to obtain compound 102 (20.45 g). The solid purity detected by HPLC was ≥99.95%. Mass spectrum m / z: 836.2661 (theoretical value: 836.2648). Theoretical element content (%) C 55 H 32 N 8 O 2 :C, 78.93;H, 3.85;N, 13.39. Measured element content (%): C, 78.96;H, 3.80;N, 13.43.

[0205] Synthesis Example 8: Preparation of Compound 123

[0206]

[0207] According to the same preparation method as compound 4 in Synthesis Example 1, b-4 was replaced by an equal mole of b-123, and c-4 was replaced by an equal mole of c-123 to obtain compound 123 (19.32 g). The solid purity detected by HPLC was ≥99.93%. Mass spectrum m / z: 848.2331 (theoretical value: 848.2320). Theoretical element content (%) C 60 H 36 N 2 S 2 :C, 84.88;H, 4.27;N, 3.30. Measured element content (%): C, 84.93;H, 4.24;N, 3.34.

[0208] Synthesis Example 9: Preparation of Compound 127

[0209]

[0210] Synthesis of intermediate C-127:

[0211] According to the same preparation method of intermediate C-4 in Synthesis Example 1, b-4 was replaced with an equal molar amount of b-127 to obtain intermediate C-127 (34.25 g). The solid purity detected by HPLC was ≥99.91%.

[0212] Synthesis of intermediate D-127:

[0213] Under nitrogen protection, C-127 (36.16 g, 82.50 mmol), raw material d-127 (14.36 g, 75.00 mmol), Pd(PPh 3 ) 4(260 mg, 0.225 mmol), K 2 CO 3 (15.55 g, 112.50 mmol) and 200 mL toluene, 70 mL ethanol, 70 mL water, stir the mixture, and heat the above reactant system to reflux for 5.5 hours. After the reaction is completed, cool to room temperature, filter to obtain a filter cake, and rinse the filter cake with ethanol. Finally, the filter cake is recrystallized with toluene / methanol = 6:1 to obtain intermediate D-127 (23.47 g, 74%); HPLC purity ≥ 99.79%.

[0214] Synthesis of intermediate E-127:

[0215] Under nitrogen protection, D-127 (21.14 g, 50.00 mmol), biboric acid pinacol ester (13.97 g, 55.00 mmol), K 2 CO 3 (10.37g,75.00mmol), Pd(dppf)Cl 2 (183 mg, 0.25 mmol), 250 ml THF, react under reflux for 7.5 hours. After the reaction is completed, cool to room temperature, add water, filter to obtain a filter cake, and recrystallize with toluene / ethanol = 9:1 to obtain intermediate E-127 (19.29, 75%); HPLC purity ≥ 99.87%.

[0216] Synthesis of compound 127:

[0217] Under nitrogen protection, E-127 (16.97 g, 33.00 mmol), c-96 (12.15 g, 30.00 mmol), K 2 CO 3 (6.22 g, 45.00 mmol), Pd(OAc) 2 (135 mg, 0.60 mmol), P(t-Bu) 3 (121 mg, 0.60 mmol), 120 ml THF, react under reflux for 10 hours. After the reaction is completed, cool to room temperature, add water, extract with dichloromethane, and the organic layer is washed with anhydrous MgSO 4 Dry, remove the solvent under reduced pressure, and recrystallize from toluene to obtain compound 127 (17.03 g, 75%); HPLC purity ≥ 99.92%. Mass spectrum m / z: 756.2534 (theoretical value: 756.2525). Theoretical element content (%) C 53 H 32 N 4 O 2:C, 84.11;H, 4.26;N, 7.40. Measured element content (%): C, 84.15;H, 4.21;N, 7.43.

[0218] Synthesis Example 10: Preparation of Compound 136

[0219]

[0220] According to the same preparation method as compound 127 in Synthesis Example 9, d-127 was replaced by an equal molar amount of d-136 to obtain compound 136 (16.88 g). The solid purity detected by HPLC was ≥99.96%. Mass spectrum m / z: 760.2785 (theoretical value: 760.2776). Theoretical element content (%) C 53 H 28 D 4 N 4 O 2 :C, 83.66;H, 4.77;N, 7.36. Measured element content (%): C, 83.70;H, 4.72;N, 7.39.

[0221] Synthesis Example 11: Preparation of Compound 144

[0222]

[0223] According to the same preparation method as compound 127 in Synthesis Example 9, a-4 was replaced by an equal molar amount of a-144, b-127 was replaced by an equal molar amount of b-144, and d-127 was replaced by an equal molar amount of d-144 to obtain compound 144 (16.44 g). The solid purity detected by HPLC was ≥99.93%. Mass spectrum m / z: 761.2631 (theoretical value: 761.2619). Theoretical element content (%) C 51 H 27 D 3 N 6 O 2 :C, 80.40; H, 4.37; N, 11.03. Measured element content (%): C, 80.45; H, 4.33; N, 11.07.

[0224] Synthesis Example 12: Preparation of Compound 150

[0225]

[0226] According to the same preparation method as compound 127 in Synthesis Example 9, a-4 was replaced by an equal mole of a-150, and d-127 was replaced by an equal mole of d-150 to obtain compound 150 (15.48 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 781.2488 (theoretical value: 781.2478). Theoretical element content (%) C 54 H 31 N 5 O 2 :C, 82.95;H, 4.00;N, 8.96. Measured element content (%): C, 82.90;H, 4.03;N, 8.92.

[0227] Synthesis Example 13: Preparation of Compound 151

[0228]

[0229] According to the same preparation method as compound 127 in Synthesis Example 9, d-127 was replaced with an equal molar amount of d-151 to obtain compound 151 (17.43 g). The solid purity was ≥99.92% as determined by HPLC. Mass spectrum m / z: 796.2852 (theoretical value: 796.2838). Theoretical element content (%) C 56 H 36 N 4 O 2 :C, 84.40;H, 4.55;N, 7.03. Measured element content (%): C, 84.45;H, 4.51;N, 7.07.

[0230] Synthesis Example 14: Preparation of Compound 160

[0231]

[0232] According to the same preparation method as compound 127 in Synthesis Example 9, b-127 was replaced by an equal molar amount of b-160, d-127 was replaced by an equal molar amount of d-144, and c-96 was replaced by an equal molar amount of c-160 to obtain compound 160 (16.73 g). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 857.2802 (theoretical value: 857.2791). Theoretical element content (%) C 60 H 35 N 5 O 2 :C, 84.00; H, 4.11; N, 8.16. Measured element content (%): C, 84.05; H, 4.08; N, 8.20.

[0233] Synthesis Example 15: Preparation of Compound 163

[0234]

[0235] According to the same preparation method as compound 127 in Synthesis Example 9, b-127 was replaced by an equal molar amount of b-163, d-127 was replaced by an equal molar amount of d-144, and c-96 was replaced by an equal molar amount of c-160 to obtain compound 163 (17.73 g). The solid purity was ≥99.92% as determined by HPLC. Mass spectrum m / z: 869.3743 (theoretical value: 869.3730). Theoretical element content (%) C 60 H 47 N 5 O 2 :C, 82.83;H, 5.45;N, 8.05. Measured element content (%): C, 82.86;H, 5.41;N, 8.10.

[0236] Synthesis Example 16: Preparation of Compound 179

[0237]

[0238]

[0239] According to the same preparation method as compound 127 in Synthesis Example 9, b-127 was replaced by an equal mole of b-179, and d-127 was replaced by an equal mole of d-179 to obtain compound 179 (16.70 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 806.1983 (theoretical value: 806.1974). Theoretical element content (%) C 53 H 31 FN 4 S 2 :C, 78.88;H, 3.87;N, 6.94. Measured element content (%): C, 78.93;H, 3.83;N, 6.98.

[0240] Synthesis Example 17: Preparation of Compound 194

[0241]

[0242] According to the same preparation method as compound 127 in Synthesis Example 9, b-127 was replaced with an equal molar amount of b-194 to obtain compound 194 (16.08 g). The solid purity was ≥99.91% as determined by HPLC. Mass spectrum m / z: 754.2635 (theoretical value: 754.2620). Theoretical element content (%) C 55 H 34 N 2 O 2:C, 87.51;H, 4.54;N, 3.71. Measured element content (%): C, 87.56;H, 4.50;N, 3.74.

[0243] Synthesis Example 18: Preparation of Compound 211

[0244]

[0245] According to the same preparation method as compound 127 in Synthesis Example 9, a-4 was replaced by an equal mole of a-211, and b-127 was replaced by an equal mole of b-211 to obtain compound 211 (16.32 g). The solid purity detected by HPLC was ≥99.98%. Mass spectrum m / z: 811.2130 (theoretical value: 811.2116). Theoretical element content (%) C 56 H 33 N 3 S 2 :C, 82.83;H, 4.10;N, 5.17. Measured element content (%): C, 82.86;H, 4.15;N, 5.13.

[0246] Synthesis Example 19: Preparation of Compound 212

[0247]

[0248] According to the same preparation method as compound 127 in Synthesis Example 9, C-127 was replaced by an equal mole of C-212, and C-96 was replaced by an equal mole of C-10 to obtain compound 212 (14.63 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 706.2385 (theoretical value: 706.2369). Theoretical element content (%) C 49 H 30 N 4 O 2 :C, 83.27;H, 4.28;N, 7.93. Measured element content (%): C, 83.30;H, 4.23;N, 7.97.

[0249] Synthesis Example 20: Preparation of Compound 218

[0250]

[0251] According to the same preparation method as compound 127 in Synthesis Example 9, b-127 was replaced by an equal mole of b-218, and c-96 was replaced by an equal mole of c-218 to obtain compound 218 (16.61 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 838.2241 (theoretical value: 838.2225). Theoretical element content (%) C57 H 34 N 4 S 2 :C, 81.60;H, 4.08;N, 6.68. Measured element content (%): C, 81.65;H, 4.04;N, 6.71.

[0252] Synthesis Example 21: Preparation of Compound 220

[0253]

[0254] Synthesis of intermediate c-220:

[0255] Under nitrogen protection, f-220 (9.12 g, 45.00 mmol), g-220 (10.64 g, 54.00 mmol), CuI (857 mg, 4.50 mmol), Cs 2 CO 3 (29.32g, 90.00mmol), 1,10-phenanthroline (1.62g, 9.00mmol), DMF (200ml), react under reflux for 24 hours. After the reaction, cool to room temperature, dilute with 400mL ethyl acetate, and then filter with a silica gel plug. The filtrate is concentrated under reduced pressure and purified by silica gel column chromatography (n-hexane: ethyl acetate = 1:1) to obtain c-220 (11.76g, 82%); HPLC purity ≥99.82%.

[0256] According to the same preparation method as compound 127 in Synthesis Example 9, b-127 was replaced by an equal molar amount of b-179, d-127 was replaced by an equal molar amount of d-144, and c-96 was replaced by an equal molar amount of c-220 to obtain compound 218 (14.55 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 702.1933 (theoretical value: 702.1912). Theoretical element content (%) C 46 H 30 N 4 S 2 :C, 78.60;H, 4.30;N, 7.97. Measured element content (%): C, 78.64;H, 4.33;N, 7.93.

[0257] Synthesis Example 22: Preparation of Compound 223

[0258]

[0259] According to the same preparation method as compound 127 in Synthesis Example 9, b-127 was replaced by an equal molar amount of b-223, d-127 was replaced by an equal molar amount of d-144, and c-96 was replaced by an equal molar amount of c-223 to obtain compound 223 (16.69 g). The solid purity was ≥99.93% as determined by HPLC. Mass spectrum m / z: 856.3077 (theoretical value: 856.3090). Theoretical element content (%) C 63 H 40 N 2 O 2 :C, 88.29;H, 4.70;N, 3.27. Measured element content (%): C, 88.32;H, 4.65;N, 3.31.

[0260] Synthesis Example 23: Preparation of Compound 231

[0261]

[0262] According to the same preparation method as compound 127 in Synthesis Example 9, a-4 was replaced by an equal molar amount of a-231, b-127 was replaced by an equal molar amount of b-231, and c-96 was replaced by an equal molar amount of c-231 to obtain compound 231 (16.70 g). The solid purity detected by HPLC was ≥99.95%. Mass spectrum m / z: 869.2613 (theoretical value: 869.2602). Theoretical element content (%) C 58 H 33 F 2 N 5 O 2 :C, 80.08; H, 3.82; N, 8.05. Measured element content (%): C, 80.13; H, 3.79; N, 8.09.

[0263] Synthesis Example 24: Preparation of Compound 241

[0264]

[0265] According to the same preparation method as compound 127 in Synthesis Example 9, d-127 was replaced by an equal mole of d-144, and c-96 was replaced by an equal mole of c-241 to obtain compound 241 (16.78 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 756.2534 (theoretical value: 756.2525). Theoretical element content (%) C 53 H 32 N 4 O 2 :C, 84.11;H, 4.26;N, 7.40. Measured element content (%): C, 84.14;H, 4.31;N, 7.36.

[0266] Synthesis Example 25: Preparation of Compound 243

[0267]

[0268] According to the same preparation method as compound 127 in Synthesis Example 9, b-127 was replaced by an equal mole of b-243, d-127 was replaced by an equal mole of d-144, and c-96 was replaced by an equal mole of c-243 to obtain compound 243 (16.93 g). The solid purity was ≥99.92% as determined by HPLC. Mass spectrum m / z: 806.2444 (theoretical value: 806.2430). Theoretical element content (%) C 55 H 30 N 6 O 2 :C, 81.87;H, 3.75;N, 10.42. Measured element content (%): C, 81.90;H, 3.71;N, 10.45.

[0269] Synthesis Example 26: Preparation of Compound 260

[0270]

[0271] According to the same preparation method as compound 127 in Synthesis Example 9, a-4 was replaced by an equal molar amount of a-260, b-127 was replaced by an equal molar amount of b-4, d-127 was replaced by an equal molar amount of d-144, and c-96 was replaced by an equal molar amount of c-260 to obtain compound 260 (17.28 g). The solid purity detected by HPLC was ≥99.96%. Mass spectrum m / z: 835.2682 (theoretical value: 835.2696). Theoretical element content (%) C 56 H 33 N 7 O 2 :C, 80.46;H, 3.98;N, 11.73. Measured element content (%): C, 80.50;H, 3.93;N, 11.76.

[0272] Synthesis Example 27: Preparation of Compound 264

[0273]

[0274] According to the same preparation method as compound 127 in Synthesis Example 9, a-4 was replaced by an equal molar amount of a-264, b-127 was replaced by an equal molar amount of b-179, d-127 was replaced by an equal molar amount of d-144, and c-96 was replaced by an equal molar amount of c-264 to obtain compound 264 (15.58 g). The solid purity was ≥99.91% as determined by HPLC. Mass spectrum m / z: 798.1547 (theoretical value: 798.1535). Theoretical element content (%) C 48 H 26 F 4 N 4 S 2 :C, 72.17;H, 3.28;N, 7.01. Measured element content (%): C, 72.22;H, 3.24;N, 7.05.

[0275] Synthesis Example 28: Preparation of Compound 270

[0276]

[0277] According to the same preparation method as compound 127 in Synthesis Example 9, b-127 was replaced by an equal mole of b-270, and c-96 was replaced by an equal mole of c-270 to obtain compound 270 (16.79 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 810.2503 (theoretical value: 810.2492). Theoretical element content (%) C 53 H 30 N 8 O 2 :C, 78.51;H, 3.73;N, 13.82. Measured element content (%): C, 78.56;H, 3.70;N, 13.86.

[0278] Synthesis Example 29: Preparation of Compound 288

[0279]

[0280]

[0281] According to the same preparation method as compound 127 in Synthesis Example 9, d-127 was replaced with an equal molar amount of d-288 to obtain compound 288 (18.23 g). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 832.2856 (theoretical value: 832.2838). Theoretical element content (%) C 59 H 36 N 4 O 2:C, 85.08;H, 4.36;N, 6.73. Measured element content (%): C, 85.05;H, 4.41;N, 6.69.

[0282] Synthesis Example 30: Preparation of Compound 308

[0283]

[0284] According to the same preparation method as compound 127 in Synthesis Example 9, a-4 was replaced by an equal mole of a-308, and d-127 was replaced by an equal mole of d-308 to obtain compound 308 (16.77 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 846.3004 (theoretical value: 846.2995). Theoretical element content (%) C 60 H 38 N 4 O 2 :C, 85.08;H, 4.52;N, 6.61. Measured element content (%): C, 85.13;H, 4.49;N, 6.64.

[0285] Synthesis Example 31: Preparation of Compound 311

[0286]

[0287] According to the same preparation method as compound 127 in Synthesis Example 9, b-127 was replaced by an equal mole of b-311, and d-127 was replaced by an equal mole of d-311 to obtain compound 311 (18.25 g). The solid purity detected by HPLC was ≥99.93%. Mass spectrum m / z: 844.3579 (theoretical value: 844.3591). Theoretical element content (%) C 59 H 24 D 12 N 4 O 2 :C, 83.86;H, 5.72;N, 6.63. Measured element content (%): C, 83.90;H, 5.67;N, 6.66.

[0288] Synthesis Example 32: Preparation of Compound 322

[0289]

[0290] According to the same preparation method as compound 127 in Synthesis Example 9, b-127 was replaced by an equal mole of b-179, and d-127 was replaced by an equal mole of d-322 to obtain compound 322 (18.17 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 864.2392 (theoretical value: 864.2381). Theoretical element content (%) C 59 H 36 N 4 S 2 :C, 81.92;H, 4.19;N, 6.48. Measured element content (%): C, 81.97;H, 4.16;N, 6.52.

[0291] Synthesis Example 33: Preparation of Compound 365

[0292]

[0293] According to the same preparation method as compound 127 in Synthesis Example 9, a-4 was replaced by an equal molar amount of a-365, b-127 was replaced by an equal molar amount of b-365, d-127 was replaced by an equal molar amount of d-365, and c-96 was replaced by an equal molar amount of c-10 to obtain compound 365 (16.94 g). The solid purity detected by HPLC was ≥99.94%. Mass spectrum m / z: 910.1978 (theoretical value: 910.1990). Theoretical element content (%) C 52 H 27 F 9 N 4 O 2 :C, 68.57; H, 2.99; N, 6.15. Measured element content (%): C, 68.53; H, 2.96; N, 6.20.

[0294] Synthesis Example 34: Preparation of Compound 370

[0295]

[0296] According to the same preparation method as compound 127 in Synthesis Example 9, b-127 was replaced by an equal molar amount of b-370, d-127 was replaced by an equal molar amount of d-288, and c-96 was replaced by an equal molar amount of c-370 to obtain compound 370 (15.50 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 794.2946 (theoretical value: 794.2933). Theoretical element content (%) C 58 H 38 N 2 O 2:C, 87.63; H, 4.82; N, 3.52. Measured element content (%): C, 87.67; H, 4.85; N, 3.49.

[0297] Synthesis Example 35: Preparation of Compound 374

[0298]

[0299] According to the same preparation method as compound 127 in Synthesis Example 9, a-4 was replaced by an equal molar amount of a-374, d-127 was replaced by an equal molar amount of d-374, and c-96 was replaced by an equal molar amount of c-243 to obtain compound 374 (17.74 g). The solid purity detected by HPLC was ≥99.92%. Mass spectrum m / z: 833.2913 (theoretical value: 833.2901). Theoretical element content (%) C 59 H 35 DN 4 O 2 :C, 84.97;H, 4.47;N, 6.72. Measured element content (%): C, 84.93;H, 4.51;N, 6.68.

[0300] Synthesis Example 36: Preparation of Compound 393

[0301]

[0302] According to the same preparation method as compound 127 in Synthesis Example 9, b-127 was replaced by an equal mole of b-211, d-127 was replaced by an equal mole of d-288, and c-96 was replaced by an equal mole of c-393 to obtain compound 393 (16.83 g). The solid purity was ≥99.97% by HPLC. Mass spectrum m / z: 862.2487 (theoretical value: 862.2476). Theoretical element content (%) C 61 H 38 N 2 S 2 :C, 84.89;H, 4.44;N, 3.25. Measured element content (%): C, 84.85;H, 4.48;N, 3.22.

[0303] Synthesis Example 37: Preparation of Compound 419

[0304]

[0305]

[0306] According to the same preparation method as compound 127 in Synthesis Example 9, b-127 was replaced by an equal molar amount of b-194, d-127 was replaced by an equal molar amount of d-419, and c-96 was replaced by an equal molar amount of c-10 to obtain compound 419 (16.15 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 780.2790 (theoretical value: 780.2777). Theoretical element content (%) C 57 H 36 N 2 O 2 :C, 87.67;H, 4.65;N, 3.59. Measured element content (%): C, 87.70;H, 4.60;N, 3.56.

[0307] Synthesis Example 38: Preparation of Compound 423

[0308]

[0309] According to the same preparation method as compound 127 in Synthesis Example 9, d-127 was replaced with an equal molar amount of d-423 to obtain compound 423 (19.61 g). The solid purity was ≥99.93% as determined by HPLC. Mass spectrum m / z: 908.3160 ​​(theoretical value: 908.3151). Theoretical element content (%) C 65 H 40 N 4 O 2 :C, 85.88;H, 4.44;N, 6.16. Measured element content (%): C, 85.83;H, 4.49;N, 6.12.

[0310] Synthesis Example 39: Preparation of Compound 435

[0311]

[0312] According to the same preparation method as compound 127 in Synthesis Example 9, b-127 was replaced by an equal mole of b-179, and d-127 was replaced by an equal mole of d-435 to obtain compound 435 (18.05 g). The solid purity was ≥99.95% by HPLC. Mass spectrum m / z: 940.2682 (theoretical value: 940.2694). Theoretical element content (%) C 65 H 40 N 4 S 2 :C, 82.95;H, 4.28;N, 5.95. Measured element content (%): C, 83.00;H, 4.24;N, 5.92.

[0313] Synthesis Example 40: Preparation of Compound 449

[0314]

[0315] According to the same preparation method as compound 127 in Synthesis Example 9, d-127 was replaced by an equal mole of d-419, and c-96 was replaced by an equal mole of c-260 to obtain compound 449 (18.49 g). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 832.2849 (theoretical value: 832.2838). Theoretical element content (%) C 59 H 36 N 4 O 2 :C, 85.08;H, 4.36;N, 6.73. Measured element content (%): C, 85.11;H, 4.32;N, 6.76.

[0316] Synthesis Example 41: Preparation of Compound 463

[0317]

[0318] According to the same preparation method as compound 127 in Synthesis Example 9, a-4 was replaced by an equal molar amount of a-463, b-127 was replaced by an equal molar amount of b-194, d-127 was replaced by an equal molar amount of d-463, and c-96 was replaced by an equal molar amount of c-463 to obtain compound 463 (15.01 g). The solid purity was ≥99.92% by HPLC. Mass spectrum m / z: 781.2486 (theoretical value: 781.2478). Theoretical element content (%) C 54 H 31 N 5 O 2 :C, 82.95;H, 4.00;N, 8.96. Measured element content (%): C, 82.99;H, 4.04;N, 8.92.

[0319] Synthesis Example 42: Preparation of Compound 464

[0320]

[0321] According to the same preparation method as compound 127 in Synthesis Example 9, d-127 was replaced with an equal molar amount of d-464 to obtain compound 464 (15.96 g). The solid purity detected by HPLC was ≥99.94%. Mass spectrum m / z: 806.2695 (theoretical value: 806.2682). Theoretical element content (%) C 57 H 34 N 4 O 2:C, 84.84;H, 4.25;N, 6.94. Measured element content (%): C, 84.88;H, 4.22;N, 6.98.

[0322] Synthesis Example 43: Preparation of Compound 499

[0323]

[0324] According to the same preparation method as compound 127 in Synthesis Example 9, d-127 was replaced by an equal mole of d-499, and c-96 was replaced by an equal mole of c-243 to obtain compound 499 (16.22 g). The solid purity was ≥99.91% by HPLC. Mass spectrum m / z: 806.2691 (theoretical value: 806.2682). Theoretical element content (%) C 57 H 34 N 4 O 2 :C, 84.84;H, 4.25;N, 6.94. Measured element content (%): C, 84.87;H, 4.22;N, 6.98.

[0325] Synthesis Example 44: Preparation of Compound 502

[0326]

[0327] According to the same preparation method as compound 127 in Synthesis Example 9, b-127 was replaced by an equal molar amount of b-179, d-127 was replaced by an equal molar amount of d-463, and c-96 was replaced by an equal molar amount of c-502 to obtain compound 502 (16.80 g). The solid purity detected by HPLC was ≥99.98%. Mass spectrum m / z: 888.2395 (theoretical value: 888.2381). Theoretical element content (%) C 61 H 36 N 4 S 2 :C, 82.41;H, 4.08;N, 6.30. Measured element content (%): C, 82.44;H, 4.05;N, 6.34.

[0328] Synthesis Example 45: Preparation of Compound 520

[0329]

[0330]

[0331] According to the same preparation method as compound 127 in Synthesis Example 9, d-127 was replaced with an equal molar amount of d-520 to obtain compound 520 (15.46 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 757.2490 (theoretical value: 757.2478). Theoretical element content (%) C 52 H 31 N 5 O 2 :C, 82.41;H, 4.12;N, 9.24. Measured element content (%): C, 82.45;H, 4.09;N, 9.27.

[0332] Synthesis Example 46: Preparation of Compound 530

[0333]

[0334] According to the same preparation method as compound 127 in Synthesis Example 9, a-4 was replaced by an equal molar amount of a-530, b-127 was replaced by an equal molar amount of b-530, and d-127 was replaced by an equal molar amount of d-530 to obtain compound 530 (14.84 g). The solid purity was ≥99.92% as determined by HPLC. Mass spectrum m / z: 760.2350 (theoretical value: 760.2335). Theoretical element content (%) C 49 H 28 N 8 O 2 :C, 77.36;H, 3.71;N, 14.73. Measured element content (%): C, 77.40;H, 3.68;N, 14.77.

[0335] Synthesis Example 47: Preparation of Compound 556

[0336]

[0337] According to the same preparation method as compound 127 in Synthesis Example 9, b-127 was replaced by an equal molar amount of b-179, d-127 was replaced by an equal molar amount of d-556, and c-96 was replaced by an equal molar amount of c-160 to obtain compound 556 (16.89 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 866.2294 (theoretical value: 866.2286). Theoretical element content (%) C 57 H 34 N 6 S 2 :C, 78.96;H, 3.95;N, 9.69. Measured element content (%): C, 78.91;H, 4.00;N, 9.66.

[0338] Synthesis Example 48: Preparation of Compound 570

[0339]

[0340] According to the same preparation method as compound 127 in Synthesis Example 9, a-4 was replaced by an equal molar amount of a-570, b-127 was replaced by an equal molar amount of b-370, d-127 was replaced by an equal molar amount of d-570, and c-96 was replaced by an equal molar amount of c-570 to obtain compound 570 (15.65 g). The solid purity was ≥99.93% as determined by HPLC. Mass spectrum m / z: 755.2585 (theoretical value: 755.2573). Theoretical element content (%) C 54 H 33 N 3 O 2 :C, 85.81;H, 4.40;N, 5.56. Measured element content (%): C, 85.87;H, 4.37;N, 5.52.

[0341] Device Embodiment

[0342] In the present invention, the ITO / Ag / ITO or ITO glass substrate is ultrasonically cleaned twice with 5% glass cleaning liquid, each time for 20 minutes, and then ultrasonically cleaned twice with deionized water, each time for 10 minutes. Acetone and isopropyl ketone are ultrasonically cleaned for 20 minutes in sequence, and dried at 120°C. The organic materials are all sublimated, and the purity is above 99.99%.

[0343] The test software, computer, K2400 digital source meter produced by Keithley Company of the United States and PR788 spectrum scanning luminance meter produced by PhotoResearch Company of the United States are combined into a joint IVL test system to test the driving voltage, luminous efficiency and CIE color coordinates of organic electroluminescent devices. The life test adopts the M6000 OLED life test system of McScience Company. The test environment is atmospheric environment and the temperature is room temperature.

[0344] Example 1: Preparation of organic electroluminescent device 1

[0345] Vacuum evaporation of β-NPB:MoO on ITO anode 3=4:1 (wt%) as a hole injection layer with a thickness of 55nm; β-NPB is vacuum evaporated on the hole injection layer as a hole transport layer with a thickness of 10nm; CzPA:PCBAPA (9wt%) is vacuum evaporated on the hole transport layer to form a light-emitting layer with a thickness of 35nm; the compound 23 of the present invention is vacuum evaporated on the light-emitting layer as an electron transport layer with a thickness of 30nm; LiF is vacuum evaporated on the electron transport layer as an electron injection layer with a thickness of 1.1nm; Al is vacuum evaporated on the electron injection layer as a cathode with a thickness of 150nm.

[0346] Examples 2 to 13: Preparation of organic electroluminescent devices 2 to 13

[0347] Organic electroluminescent devices 2 to 13 were obtained by replacing compound 23 in the electron transport layer of Example 1 with compound 127, compound 136, compound 150, compound 151, compound 194, compound 211, compound 231, compound 241, compound 270, compound 464, compound 502 and compound 520, respectively, while keeping the other properties the same.

[0348] Comparative Example 1: Preparation of Comparative Organic Electroluminescent Device 1

[0349] The comparative organic electroluminescent device 1 was obtained by replacing the compound 23 in the electron transport layer of Example 1 with R-ET and keeping the other conditions the same.

[0350]

[0351] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 1 to 13 of the present invention and Comparative Example 1 are shown in Table 1.

[0352] Table 1 Test data of luminescence characteristics of organic electroluminescent devices

[0353]

[0354] It can be concluded from Table 1 that, compared with Comparative Example 1, the organic electroluminescent devices 1 to 13 of the present invention have excellent photoelectric properties, specifically, lower driving voltage, higher luminous efficiency, and longer service life. This shows that the imidazole compound of Formula 1 of the present invention has good electron mobility, can effectively transmit electrons, and is an organic electroluminescent material with good performance.

[0355] Example 14: Preparation of organic electroluminescent device 14

[0356] HT-1:p-HI1 (5wt%) was vacuum evaporated on the ITO anode as a hole injection layer with a thickness of 22nm; HT-1 was vacuum evaporated on the hole injection layer as a hole transport layer with a thickness of 95nm; EB-1 was vacuum evaporated on the hole transport layer as an electron blocking layer with a thickness of 15nm; BCzPh and compound 4 of the present invention were vacuum evaporated on the electron blocking layer at a ratio of 1:1, and the dopant TEG was evaporated at a doping amount of 11wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 35nm; ET-1:Liq=1:1 (wt%) was vacuum evaporated on the light-emitting layer as an electron transport layer with a thickness of 31nm; LiF was vacuum evaporated on the electron transport layer as an electron injection layer with a thickness of 1.2nm; Al was vacuum evaporated on the electron injection layer as a cathode with a thickness of 200nm.

[0357] Examples 15 to 37: Preparation of organic electroluminescent devices 15 to 37

[0358] The compound 4 in the light-emitting layer of Example 14 was replaced with compound 10, compound 23, compound 96, compound 127, compound 136, compound 160, compound 163, compound 194, compound 211, compound 212, compound 243, compound 260, compound 264, compound 270, compound 288, compound 370, compound 374, compound 393, compound 419, compound 464, compound 502, compound 520, and compound 530, respectively, and the rest was the same, to obtain organic electroluminescent devices 15 to 37.

[0359] Comparative Example 2: Preparation of Comparative Organic Electroluminescent Device 2

[0360] The compound 4 in the light-emitting layer of Example 14 was replaced with RH, and the other conditions were the same, to obtain a comparative organic electroluminescent device 2.

[0361]

[0362] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 14 to 37 of the present invention and Comparative Example 2 are shown in Table 2.

[0363] Table 2 Test data of luminescence characteristics of organic electroluminescent devices

[0364]

[0365]

[0366] It can be concluded from Table 2 that, compared with Comparative Example 2, the organic electroluminescent devices 14 to 37 of the present invention have excellent photoelectric performance, specifically, lower driving voltage, higher luminous efficiency and longer service life, indicating that the imidazole compound of Formula 1 of the present invention is an organic electroluminescent material with good performance.

[0367] Example 38: Preparation of organic electroluminescent device 38

[0368] HT-1:p-HI2 (5 wt%) was vacuum-deposited on the ITO anode as a hole injection layer with a thickness of 22 nm; HT-1 was vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 95 nm; EB-1 was vacuum-deposited on the hole transport layer as an electron blocking layer with a thickness of 15 nm; RH-1 and the compound 30 of the present invention were vacuum-deposited on the electron blocking layer at a ratio of 1:1, and the dopant Ir (mphmq) was added. 2 Acac was evaporated with a doping amount of 6wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 35nm; ET-1:Liq=1:1 (wt%) was vacuum evaporated on the light-emitting layer as an electron transport layer with a thickness of 31nm; LiF was vacuum evaporated on the electron transport layer as an electron injection layer with a thickness of 1.2nm; Al was vacuum evaporated on the electron injection layer as a cathode with a thickness of 200nm.

[0369] Examples 39 to 59: Preparation of organic electroluminescent devices 39 to 59

[0370] The compound 30 in the light-emitting layer of Example 38 was replaced with compound 49, compound 102, compound 123, compound 144, compound 150, compound 179, compound 218, compound 223, compound 231, compound 241, compound 308, compound 311, compound 322, compound 365, compound 423, compound 435, compound 449, compound 463, compound 499, compound 556, and compound 570, respectively, while the other parts were the same, to obtain organic electroluminescent devices 39 to 59.

[0371] Comparative Example 3: Preparation of Comparative Organic Electroluminescent Device 3

[0372] The compound 30 in the light-emitting layer of Example 38 was replaced by RH, and the other conditions were the same, to obtain a comparative organic electroluminescent device 3.

[0373]

[0374]

[0375] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 38 to 59 of the present invention and Comparative Example 3 are shown in Table 3.

[0376] Table 3 Test data of luminescence characteristics of organic electroluminescent devices

[0377]

[0378] It can be concluded from Table 3 that, compared with Comparative Example 3, the organic electroluminescent devices 38 to 59 of the present invention have excellent photoelectric performance, specifically, lower driving voltage, higher luminous efficiency and longer service life, indicating that the imidazole compound of Formula 1 of the present invention is an organic electroluminescent material with good performance.

[0379] This indicates that the imidazole compound of formula 1 of the present invention, when used together as an n-type host material and a p-type host material, can effectively balance electrons and holes, so that electrons and holes are effectively combined into excitons in the light-emitting layer to emit light.

[0380] Example 60: Preparation of organic electroluminescent device 60

[0381] HAT-CN was vacuum-deposited on the ITO / Ag / ITO anode as a hole injection layer with a thickness of 11 nm; NPB was vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 75 nm; MCBP:Ir(ppy) was vacuum-deposited on the hole transport layer 2 (m-bppy) (doped with 10wt%) to form a light-emitting layer with a thickness of 30nm; TPBI was vacuum-deposited on the light-emitting layer as an electron transport layer with a thickness of 42nm; LiF was vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 1.2nm; Mg:Ag=1:9 (wt%) was vacuum-deposited on the electron injection layer as a cathode with a thickness of 15nm; and the compound 127 of the present invention was vacuum-deposited on the cathode as a covering layer with a thickness of 55nm.

[0382] Examples 61-72: Preparation of organic electroluminescent devices 61-72

[0383] The compound 127 in the covering layer of Example 60 was replaced by compound 160, compound 212, compound 220, compound 223, compound 231, compound 241, compound 260, compound 288, compound 393, compound 423, compound 499 and compound 556 respectively, while the other parts were the same, to obtain organic electroluminescent devices 61 to 72.

[0384] Comparative Example 4: Preparation of Comparative Organic Electroluminescent Device 4

[0385] The compound 127 in the covering layer of Example 60 was replaced with R-CP, and the other conditions were the same, to obtain a comparative organic electroluminescent device 4.

[0386]

[0387] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 60 to 72 of the present invention and Comparative Example 4 are shown in Table 4.

[0388] Table 4 Test data of luminescence characteristics of organic electroluminescent devices

[0389]

[0390]

[0391] It can be concluded from Table 4 that, compared with Comparative Example 4, the organic electroluminescent devices 60 to 72 of the present invention have relatively excellent photoelectric properties, specifically, higher luminous efficiency and longer service life. This shows that when the imidazole compound of Formula 1 of the present invention is used as a covering layer, it can effectively couple out the light trapped in the device and improve the luminous efficiency of the device. This shows that the imidazole compound of Formula 1 of the present invention is an organic electroluminescent material with good performance.

[0392] It should be noted that the present invention is particularly described using individual embodiments. However, without departing from the principles of the present invention, a person skilled in the art may make various improvements in form or detail to the present invention, and these improvements also fall within the scope of protection of the present invention.

Claims

1. An imidazole compound, characterized in that, the imidazole compound is selected from the structures shown below, wherein, Ar is selected from one of the groups shown below, c1 is selected from 0, 1, 2, 3, 4; c2 is selected from 0, 1, 2; c3 is selected from 0, 1, 2, 3; Y is the same or different and is selected from C(Ry); Ry is the same or different and is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted phenyl; The R 0 is selected from one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted indanyl group, and a substituted or unsubstituted tetrahydronaphthyl group; the substituents represented by "substituted" in the substituted or unsubstituted phenyl group include the following groups: deuterium, tritium, cyano group, methyl group, ethyl group, propyl group, butyl group, wherein the methyl group in the above substituents is substituted or unsubstituted, and the substituents of the methyl group include fluorine; the substituents represented by "substituted" in the substituted or unsubstituted biphenyl group, the substituted or unsubstituted naphthyl group, the substituted or unsubstituted indanyl group, and the substituted or unsubstituted tetrahydronaphthyl group include the following groups: deuterium, tritium; The R 1 is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted phenyl, and substituted or unsubstituted pyridyl; the substituents represented by "substituted" in "substituted or unsubstituted" include the following groups: deuterium and tritium; The said A 1 , A 2 is independently selected from one of the groups shown below, d1 is selected from 0, 1, 2, 3, 4; d2 is selected from 0, 1, 2; d3 is selected from 0, 1, 2, 3; Said X 0 is selected from O or S; said E is selected from N or C(Re); Rb is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl; the substituents represented by "substituted or unsubstituted" include the following groups, deuterium, tritium, halogen; Re is independently selected from one of hydrogen, deuterium, tritium; The R 2 independently selected from one of hydrogen, deuterium, tritium, and substituted or unsubstituted phenyl; the substituents represented by "substituted or unsubstituted" include the following groups: deuterium and tritium; The X is the same or different and is selected from C(Rx) or N, and the R x is selected from one of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, and substituted or unsubstituted butyl; the substituents represented by "substituted" in "substituted or unsubstituted" include the following groups: deuterium, tritium, halogen; The said L a selected from a single bond, The L b is selected from one of a single bond or the following groups: a0 is selected from 0, 1, 2, 3, 4, 5, 6; a1 is selected from 0, 1, 2, 3, 4; a2 is selected from 0, 1, 2, 3; a3 is selected from 0, 1, 2; a4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8; Rz is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano; The R 3 is the same as or different from and is selected from one of hydrogen, deuterium, and tritium; The R 4 is the same as or different from and is selected from one of hydrogen, deuterium, and tritium; The said L 1 and L 2 are independently selected from one of a single bond or the following groups: b1 is selected from 0, 1, 2, 3, 4; b2 is selected from 0, 1, 2, 3; b3 is selected from 0, 1, 2; b5 is selected from 0, 1, 2, 3, 4, 5, 6; The said R v is the same as or different from and is selected from one of hydrogen, deuterium, and tritium.

2. The imidazole compound according to claim 1, characterized in that, Ar is selected from one of the groups shown below, c1 is selected from 0, 1, 2, 3, 4; c2 is selected from 0, 1, 2; The R 0 is selected from one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, and a substituted or unsubstituted naphthyl group; the substituents represented by "substituted" in the substituted or unsubstituted phenyl group include the following groups: deuterium and tritium; the substituents represented by "substituted" in the substituted or unsubstituted biphenyl group and the substituted or unsubstituted naphthyl group include the following groups: deuterium and tritium; The R 1 is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted phenyl, and substituted or unsubstituted pyridyl; the substituents represented by "substituted" in "substituted or unsubstituted" include the following groups: deuterium and tritium.

3. The imidazole compound according to claim 1, characterized in that, The said A 1 , A 2 is independently selected from one of the groups shown below, d1 is selected from 0, 1, 2, 3, 4; d2 is selected from 0, 1, 2; d3 is selected from 0, 1, 2, 3; The said X 0 is selected from O or S; the said E is selected from N or C(Re); Rb is the same or different and is selected from one of hydrogen, deuterium, tritium; Re is independently selected from one of hydrogen, deuterium, tritium; The R 2 Independently selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted phenyl; the substituents represented by "substituted or unsubstituted" include the following groups: deuterium and tritium.

4. The imidazole compound according to claim 1, characterized in that, The L b is selected from a single bond or one of the following groups: a0 is selected from 0, 1, 2, 3, 4, 5, 6; a1 is selected from 0, 1, 2, 3, 4; a2 is selected from 0, 1, 2, 3; Rz is the same or different and is selected from one of hydrogen, deuterium, tritium; The R 3 is the same as or different from and is one selected from hydrogen, deuterium, and tritium.

5. The imidazole compound according to claim 1, characterized in that, The said L 1 , L 2 is independently selected from one of a single bond or the groups shown below, b1 is selected from 0, 1, 2, 3, 4; Rv is the same or different and is selected from one of hydrogen, deuterium, tritium.

6. An imidazole compound, characterized in that, the imidazole compound is selected from at least one of the structures shown below, 7. An organic electroluminescent device, characterized in that, the organic electroluminescent device contains the imidazole compound according to any one of claims 1 to 6.

8. The organic electroluminescent device according to claim 7, characterized in that, The organic electroluminescent device includes an anode, a cathode, and at least one of an organic layer and a covering layer. The organic layer is located between the anode and the cathode, and the covering layer is located outside the cathode or the anode. At least one of the organic layer and the covering layer contains the imidazole compound according to any one of claims 1 to 6.

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