A heterocyclic compound and an organic electroluminescent device

Abstract

The present invention provides a heterocyclic compound and an organic electroluminescent device, relating to the technical field of organic electroluminescence. The heterocyclic compound provided by the present invention has a high hole mobility, a high glass transition temperature and good thermal stability, can effectively transfer holes, block electrons in the light-emitting layer, avoid some electrons passing through the light-emitting layer, improve the recombination probability of excitons in the light-emitting layer, and when applied to the hole transport layer in an organic electroluminescent device, can effectively improve the luminous efficiency and service life of the device; at the same time, the heterocyclic compound also has a high refractive index, and when applied to the cover layer in an organic electroluminescent device, can couple out the light trapped in the device, reduce the total internal reflection of light inside the device, enhance the light extraction efficiency of the device, thereby improving the luminous efficiency of the organic electroluminescent device and prolonging the service life of the organic electroluminescent device.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic electroluminescence, and particularly relates to a heterocyclic compound and an organic electroluminescent device thereof. Background Art

[0002] As a self-luminous element, an organic light-emitting diode (OLED for short) has the advantages of light weight, fast response speed, wide operating temperature range, low energy consumption, high efficiency, good color purity, etc., and is widely used in many fields such as lighting and display, and is one of the most promising new display technologies at present.

[0003] The light-emitting principle of OLED is as follows: Under the drive of an external voltage, holes injected from the anode and electrons injected from the cathode recombine in the light-emitting layer to generate excitons. The excitons migrate under the action of an electric field, transfer energy to the light-emitting material. Since the electrons in the excited state are extremely unstable, they will release energy in the form of light and return to the stable ground state, thus generating a light-emitting phenomenon. An OLED includes a cathode, an anode, and an organic layer. The organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a cover layer, etc. These organic functional layers play an important role in improving the performance of OLED devices such as driving voltage, luminous efficiency, color purity, and service life.

[0004] An excellent organic electroluminescent device needs to have characteristics such as high luminous efficiency and long service life. However, the current development of organic electroluminescent materials is not yet perfect, and continuous progress is still needed to prepare an excellent organic electroluminescent device. The hole transport material is an indispensable part of an organic electroluminescent device. Its function is to improve the injection and transport efficiency of holes, reduce the injection barrier of holes, and effectively block electrons in the light-emitting layer. However, most of the currently used hole transport materials have problems such as poor film-forming property and thermal stability, and low hole mobility. Therefore, it is necessary to use a hole transport material with a high hole mobility, good film-forming property and thermal stability to improve the brightness, efficiency and life of OLED devices.

[0005] In order to further improve the performance of the device such as luminous efficiency and service life, a cover layer can also be provided on the outer side of at least one of the anode and the cathode to couple out the light trapped in the device, enhance the light extraction efficiency, and thus improve the luminous efficiency of the device. However, there is little research on cover layer materials at home and abroad, and it is difficult for existing cover layer materials to simultaneously have excellent properties such as a high refractive index, a high glass transition temperature, good film-forming property and thermal stability.

[0006] Therefore, there is an urgent need to design materials with high hole mobility, relatively high refractive index, relatively high glass transition temperature and good thermal stability, so as to improve the luminous efficiency of organic light-emitting devices and extend the service life of organic light-emitting devices. Summary of the Invention

[0007] To solve the above technical problems, the present invention provides a heterocyclic compound and an organic light-emitting device thereof. When applied to the hole transport layer or the covering layer of an organic light-emitting device, it can effectively improve the luminous efficiency of the organic light-emitting device and extend the service life of the organic light-emitting device. The technical solution of the present invention is as follows:

[0008] The present invention provides a heterocyclic compound, characterized in that the heterocyclic compound is represented by the structure shown in Formula 1:

[0009]

[0010] In Formula 1,

[0011] R0 is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, a group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 alicyclic ring, or a substituted or unsubstituted 5-30 membered heteroaryl; or two adjacent R0s can be connected to form a substituted or unsubstituted ring;

[0012] a0 is independently selected from 0, 1, 2, 3 or 4;

[0013] Y is independently selected from N or CH; Y bonded to L1 or L2 is C;

[0014] L is selected from any one of substituted or unsubstituted C6-C30 arylene, a divalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 alicyclic ring, or a substituted or unsubstituted 5-30 membered heteroarylene;

[0015] L1, L2, L3, L4 are independently selected from a single bond, substituted or unsubstituted C6-C30 arylene, a divalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 alicyclic ring, or a substituted or unsubstituted 5-30 membered heteroarylene;

[0016] Ar1 is selected from Formula 2;

[0017] Ar2, Ar3, and Ar4 are each independently selected from the group consisting of hydrogen, Formula 2, a substituted or unsubstituted C6-C30 aryl group, a group formed by fusing a substituted or unsubstituted C6-C30 aromatic ring with a substituted or unsubstituted C3-C7 alicyclic ring, or a substituted or unsubstituted 5-30 membered heteroaryl group; and Ar3 and Ar4 are not hydrogen;

[0018] In Formula 2,

[0019] X is selected from O or S;

[0020] Y1 is independently selected from N or CH;

[0021] R1 and R2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a group formed by fusing a substituted or unsubstituted C6-C30 aromatic ring with a substituted or unsubstituted C3-C7 alicyclic ring, or a substituted or unsubstituted 5-30 membered heteroaryl group; or two adjacent R1 groups can be connected to form a substituted or unsubstituted ring;

[0022] a1 is selected from 0, 1, 2, 3, or 4; a2 is selected from 0, 1, or 2.

[0023] Advantageous Effects:

[0024] The present invention provides a heterocyclic compound and an organic electroluminescent device thereof. The heterocyclic compound has a high hole mobility, a high glass transition temperature, and good thermal stability, can effectively transfer holes, block electrons in the light-emitting layer, avoid some electrons passing through the light-emitting layer, improve the recombination probability of excitons in the light-emitting layer. When applied to the hole transport layer of an organic electroluminescent device, it can effectively improve the luminous efficiency and service life of the device; at the same time, the heterocyclic compound also has a high refractive index. When applied to the cover layer of an organic electroluminescent device, it can couple out the light trapped in the device, reduce the total internal reflection of light inside the device, enhance the light extraction efficiency of the device, and thus improve the luminous efficiency of the organic electroluminescent device. Specific Embodiments

[0025] The technical solutions of specific embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without making creative efforts belong to the protection scope of the present invention.

[0026] In the compounds of the present invention, any atom not specified as a particular isotope is included as any stable isotope of that atom and includes atoms in both their natural and non-natural isotope abundances.

[0027] The halogen atoms described in the present invention refer to fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0028] The alkyl groups described in the present invention refer to hydrocarbon groups formed by removing one hydrogen atom from an alkane molecule. They can be straight-chain alkyl groups or branched-chain alkyl groups, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc.; the branched-chain alkyl groups include, but are not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, isomeric groups of n-pentyl, isomeric groups of n-hexyl, isomeric groups of n-heptyl, isomeric groups of n-octyl, isomeric groups of n-nonyl, isomeric groups of n-decyl, etc. The above alkyl groups are preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl.

[0029] The cycloalkyl groups described in the present invention refer to hydrocarbon groups formed by removing one hydrogen atom from a cycloalkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, etc., but are not limited thereto. The above cycloalkyl groups are preferably cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, norbornyl.

[0030] As used herein, the term "aryl" refers to the general name of a monovalent group remaining after removing a hydrogen atom from the aromatic nucleus carbon of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl refers to an aryl having only one aromatic ring in the molecule, such as phenyl, etc., but not limited thereto; the polycyclic aryl refers to an aryl having two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, etc., but not limited thereto; the fused-ring aryl refers to an aryl having two or more aromatic rings and fused together through sharing two adjacent carbon atoms, such as naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylenyl, fluoranthenyl, spirobifluorenyl, etc., but not limited thereto. The above aryl is preferably phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl.

[0031] As used herein, the term "heteroaryl" refers to the general name of a group obtained by replacing one or more aromatic nucleus carbon atoms in an aryl with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen or phosphorus atoms, preferably having 5 to 30 ring atoms (5- to 30-membered), more preferably 6 to 24 ring atoms (6- to 24-membered), particularly preferably 6 to 13 ring atoms (6- to 13-membered), and most preferably 6 to 12 ring atoms (6- to 12-membered); in addition, preferably having 1 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms; the connection site of the heteroaryl can be located on a ring-forming carbon atom or a ring-forming nitrogen atom, and the heteroaryl can be a monocyclic heteroaryl, polycyclic heteroaryl or fused-ring heteroaryl. The monocyclic heteroaryl includes pyridyl, pyrimidinyl, triazinyl, furyl, thienyl, pyrrolyl, imidazolyl, etc., but not limited thereto; the polycyclic heteroaryl includes bipyridyl, bipyrimidinyl, phenylpyridyl, etc., but not limited thereto; the fused-ring heteroaryl includes quinolinyl, isoquinolinyl, indolyl, benzothienyl, benzofuryl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuryl, benzodibenzofuryl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiinyl, etc., but not limited thereto. The above heteroaryl is preferably pyridyl, pyrimidinyl, thienyl, furyl, benzothienyl, benzofuryl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuryl, dibenzothienyl, benzodibenzothienyl, benzodibenzofuryl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenoxathiinyl, spirofluoreneoxanthenyl, spirofluorenesulfuranthenyl, etc.

[0032] The group formed by the fusion of an aromatic ring and an alicyclic ring in the present invention refers to the general name of a monovalent group formed by removing one hydrogen atom after the fusion of an aromatic ring and an alicyclic ring (cycloalkyl, cycloalkenyl, cycloalkynyl). The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The alicyclic ring preferably has 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, still more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. Examples include benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, naphthocyclopentenyl, naphthocyclohexenyl, etc., but are not limited thereto.

[0033] In the present invention, the arylene group means an aryl group having two bonding sites, that is, a divalent group. The description of the aryl group provided above can be applied thereto, except that the arylene group is a divalent group.

[0034] The divalent group formed by the fusion of an aromatic ring and an alicyclic ring in the present invention refers to a group formed by the fusion of an aromatic ring and an alicyclic ring having two bonding sites, that is, a divalent group. The description of the group formed by the fusion of an aromatic ring and an alicyclic ring provided above can be applied thereto, except that the divalent group formed by the fusion of an aromatic ring and an alicyclic ring is a divalent group.

[0035] In the present invention, the heteroarylene group means a heteroaryl group having two bonding sites, that is, a divalent group. The description of the aryl group provided above can be applied thereto, except that the heteroarylene group is a divalent group.

[0036] "Substituted" in the present invention means that a hydrogen atom in certain functional groups is replaced by another atom or functional group (i.e., a substituent), and the substitution position is not limited as long as it is the position where the hydrogen atom is substituted. When two or more are substituted, the two or more substituents may be the same or different from each other.

[0037] The substituents in the "substituted or unsubstituted" of the present invention can be independently selected from one or more of deuterium, halogen, cyano, nitro, amino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkenyl, substituted or unsubstituted C1-C12 alkynyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C12 cycloalkenyl, substituted or unsubstituted C3-C12 cycloalkynyl, substituted or unsubstituted C3-C30 heterocyclic group, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted 5-30 membered heteroaryl, substituted or unsubstituted C6-C30 arylamino or substituted or unsubstituted C1-C30 silyl; preferably one or more of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, 5-30 membered heteroaryl. When there are multiple substituents, the multiple substituents are the same or different from each other; more preferably one or more of deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, camphenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylenyl, perylenyl, pyrenyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, phenanthrolinyl, furyl, thienyl, benzofuryl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuryl, dibenzothienyl, carbazolyl, phenothiazinyl, phenoxazinyl. When there are multiple substituents, the multiple substituents are the same or different from each other.

[0038] In the specification, "" means the part connected to another substituent. "" can be connected to any optional position of the connected group / fragment. For example means or and so on.

[0039] In this specification, when the position of the substituent on the ring is not fixed, it means that it can be connected to any one of the corresponding optional sites of the ring. For example, can represent and so on.

[0040] In this specification, when a bond where a substituent or a bonding site is located passes through two or more rings, it indicates that it can be bonded to any one of the two or more rings, and specifically can be bonded to any one of the corresponding optional sites of the ring. For example, can represent or can represent and so on.

[0041] "Linking to form a ring" as described in the present invention means that each group is connected to each other through a chemical bond, and optionally forms a double bond / triple bond, and can form an aromatic group, as exemplified below:

[0042]

[0043] In the present invention, the ring formed by linking can be an aromatic ring system, an aliphatic ring system or a ring system formed by the fusion of both, and can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring or a fused ring. Examples can include benzene, naphthalene, indene, fluorene, cyclopentene, cyclopentane, cyclopentane-fused benzene, cyclohexene, cyclohexane, cyclohexane-fused benzene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, etc., but are not limited thereto.

[0044] The present invention provides a heterocyclic compound, characterized in that the heterocyclic compound is represented by the structure shown in Formula 1:

[0045]

[0046] In Formula 1,

[0047] the R0 is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, a group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted 5-30 membered heteroaryl; or two adjacent R0s can be linked to form a substituted or unsubstituted ring;

[0048] the a0 is independently selected from 0, 1, 2, 3 or 4;

[0049] the Y is independently selected from N or CH; the Y bonded to L1 or L2 is selected from C;

[0050] the L is selected from any one of a substituted or unsubstituted C6-C30 arylene, a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted 5-30 membered heteroarylene;

[0051] L1, L2, L3, and L4 are each independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensation of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 alicyclic ring, or a substituted or unsubstituted 5-30 membered heteroarylene group;

[0052] Ar1 is selected from Formula 2;

[0053] Ar2, Ar3, and Ar4 are each independently selected from any one of hydrogen, Formula 2, a substituted or unsubstituted C6-C30 aryl group, a group formed by condensation of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 alicyclic ring, or a substituted or unsubstituted 5-30 membered heteroaryl group; and Ar3 and Ar4 are not hydrogen;

[0054] In Formula 2,

[0055] X is selected from O or S;

[0056] Y1 is independently selected from N or CH;

[0057] R1 and R2 are each independently selected from any one of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a group formed by condensation of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 alicyclic ring, or a substituted or unsubstituted 5-30 membered heteroaryl group; or two adjacent R1s can be connected to form a substituted or unsubstituted ring;

[0058] a1 is selected from 0, 1, 2, 3, or 4; a2 is selected from 0, 1, or 2.

[0059] Preferably, the substituents in the "substituted or unsubstituted" are selected from one or more of deuterium, halogen, cyano, nitro, amino, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C1-C12 alkenyl group, a substituted or unsubstituted C1-C12 alkynyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C3-C12 cycloalkenyl group, a substituted or unsubstituted C3-C12 cycloalkynyl group, a substituted or unsubstituted C3-C30 heterocyclic group, a substituted or unsubstituted C1-C12 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted 5-30 membered heteroaryl group, a substituted or unsubstituted C6-C30 arylamino group, or a substituted or unsubstituted C1-C30 silyl group. When there are multiple substituents, the multiple substituents are the same or different from each other.

[0060] More preferably, the heterocyclic compound is selected from any one of the following structures:

[0061]

[0062] Preferably, in Formula 2 R1 and R2 are independently selected from hydrogen, deuterium, cyano, halogen, trifluoromethyl, or the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, camphenyl, norbornyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, perylenyl, pyrenyl, group, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, fluorenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, acridinyl, o-phenanthrolinyl, furyl, thienyl, benzofuryl, benzothienyl, dibenzofuryl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, phenothiazinyl, phenoxazinyl; or two adjacent R1s can be connected to form a substituted or unsubstituted ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted C3-C7 aliphatic ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrimidine ring, or a substituted or unsubstituted pyrazine ring.

[0063] The substituents in the "substituted or unsubstituted" are selected from one or more of deuterium, halogen, cyano, trifluoromethyl, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, deuterated tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, camphenyl, norbornyl, phenyl, deuterated phenyl. When there are multiple substituents, the multiple substituents are the same or different from each other.

[0064] More preferably, Formula 2 is selected from any one of the following groups:

[0065]

[0066]

[0067]

[0068] Preferably, Ar2, Ar3, and Ar4 are independently selected from hydrogen, Formula 2, or any one of the following groups:

[0069]

[0070] R3 is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted 5-20 membered heteroaryl; or two adjacent R3s may be connected to form a substituted or unsubstituted ring;

[0071] X1 is selected from O, S, NR4 or CR5R6;

[0072] R4 is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C20 aryl, a group formed by fusion of a substituted or unsubstituted C6-C20 aryl ring and a substituted or unsubstituted C3-C7 alicyclic ring, and substituted or unsubstituted 5-20 membered heteroaryl; or R4 may be directly bonded to any one of L1-L4;

[0073] R5 and R6 are independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C20 aryl, a group formed by fusion of a substituted or unsubstituted C6-C20 aryl ring and a substituted or unsubstituted C3-C7 alicyclic ring, and substituted or unsubstituted 5-20 membered heteroaryl; or R5 or R6 may be directly bonded to any one of L1-L4; or R5 and R6 may be connected to form a substituted or unsubstituted ring;

[0074] X2 is selected from O, S or NR7; R7 is selected from any one of deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted 5-20 membered heteroaryl;

[0075] Z is independently selected from N or CH;

[0076] c1 is independently selected from 0, 1, 2, 3, 4 or 5; c2 is independently selected from 0, 1, 2, 3 or 4; c3 is independently selected from 0, 1, 2 or 3; c4 is independently selected from 0, 1 or 2.

[0077] Preferably, Formula 2 is as described herein.

[0078] More preferably, Ar2, Ar3, and Ar4 are independently selected from hydrogen, Formula 2, or any one of the following groups:

[0079]

[0080]

[0081]

[0082]

[0083] R3 is independently selected from hydrogen, deuterium, halogen, trifluoromethyl, cyano, or a substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, camphenyl, norbornyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, perylenyl, pyrenyl, group, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, fluorenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, acridinyl, phenanthrolinyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, phenothiazinyl, phenoxazinyl;

[0084] R4 is independently selected from hydrogen, deuterium, trifluoromethyl, or a substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, camphenyl, norbornyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, perylenyl, pyrenyl, group, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, fluorenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, acridinyl, phenanthrolinyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, phenothiazinyl, phenoxazinyl;

[0085] R5 and R6 are independently selected from hydrogen, deuterium, halogen, trifluoromethyl, cyano, or a substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, camphenyl, norbornyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, perylenyl, pyrenyl, any one of a radical, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, fluorenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, acridinyl, phenanthrolinyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, phenothiazinyl, phenoxazinyl;

[0086] R7 and R8 are independently selected from hydrogen, deuterium, halogen, trifluoromethyl, cyano, or a substituted or unsubstituted group selected from the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, camphenyl, norbornyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, perylenyl, pyrenyl; any one of a radical, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, fluorenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, acridinyl, phenanthrolinyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, phenothiazinyl, phenoxazinyl;

[0087] c0 is independently selected from 0 or 1; c1 is independently selected from 0, 1, 2, 3, 4 or 5; c2 is independently selected from 0, 1, 2, 3 or 4; c3 is independently selected from 0, 1, 2 or 3; c4 is independently selected from 0, 1 or 2; c5 is independently selected from 0, 1, 2, 3, 4, 5 or 6; c6 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; c7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; c8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; c9 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; c 10 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0088] The substituents of "substituted or unsubstituted" in R3 to R8 are independently selected from one or more of deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, deuterated tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, camphenyl, norbornyl, phenyl, deuterated phenyl. When there are multiple substituents, the multiple substituents are the same or different from each other.

[0089] Preferably, L is selected from any one of the following groups:

[0090]

[0091] R9 is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted 5-20 membered heteroaryl; or two adjacent R9s may be linked to form a substituted or unsubstituted ring;

[0092] X3 is selected from O, S, NR 10 or CR 11 R 12 ;

[0093] R 10 is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C20 aryl, a group formed by fusion of a substituted or unsubstituted C6-C20 aryl ring and a substituted or unsubstituted C3-C7 alicyclic ring, or substituted or unsubstituted 5-20 membered heteroaryl;

[0094] R 11 , R 12 are independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C20 aryl, a group formed by fusion of a substituted or unsubstituted C6-C20 aryl ring and a substituted or unsubstituted C3-C7 alicyclic ring, or substituted or unsubstituted 5-20 membered heteroaryl; or R 11 and R 12 may be linked to form a substituted or unsubstituted ring;

[0095] V is independently selected from N or CH;

[0096] d1 is independently selected from 0, 1, 2, 3 or 4; d2 is independently selected from 0, 1, 2 or 3; d3 is independently selected from 0, 1 or 2; d4 is independently selected from 0, 1, 2, 3, 4, 5 or 6; d5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0097] More preferably, L is selected from any one of the following groups:

[0098]

[0099]

[0100]

[0101] R9 is independently selected from hydrogen, deuterium, halogen, trifluoromethyl, cyano, or a substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, camphenyl, norbornyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, perylenyl, pyrenyl, group, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, fluorenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, acridinyl, o-phenanthrolyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl;

[0102] The R 10 is independently selected from hydrogen, deuterium, trifluoromethyl, or a substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, camphenyl, norbornyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, perylenyl, pyrenyl, group, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, fluorenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, acridinyl, o-phenanthrolyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl;

[0103] The R 11 and R 12 are independently selected from hydrogen, deuterium, halogen, trifluoromethyl, cyano, or a substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, camphenyl, norbornyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, perylenyl, pyrenyl, group, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, fluorenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, acridinyl, o-phenanthrolyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl;

[0104] d0 is independently selected from 0 or 1; d1 is independently selected from 0, 1, 2, 3, or 4; d2 is independently selected from 0, 1, 2, or 3; d3 is independently selected from 0, 1, or 2; d4 is independently selected from 0, 1, 2, 3, 4, 5, or 6; d5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; d6 is independently selected from 0, 1, 2, 3, 4, or 5; d7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; d8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14;

[0105] R9 to R 12 In “substituted or unsubstituted”, the substituents are independently selected from one or more of deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, deuterated tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, camphyl, norbornyl, phenyl, deuterated phenyl. When there are multiple substituents, the multiple substituents are the same or different from each other.

[0106] Preferably, L1, L2, L3, and L4 are independently selected from a single bond or any one of the following groups:

[0107]

[0108] R 13 is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted 5-20 membered heteroaryl; or two adjacent Rs 13 can be connected to form a substituted or unsubstituted ring;

[0109] X4 is selected from O, S, NR 14 or CR 15 R 16 ;

[0110] R 14 is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C20 aryl, a group formed by fusing a substituted or unsubstituted C6-C20 aryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or substituted or unsubstituted 5-20 membered heteroaryl;

[0111] R15 , R 16 is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C20 aryl, a group formed by fusion of a substituted or unsubstituted C6-C20 aromatic ring and a substituted or unsubstituted C3-C7 alicyclic ring, or substituted or unsubstituted 5-20 membered heteroaryl; or R 15 and R 16 can be connected to form a substituted or unsubstituted ring;

[0112] E is independently selected from N or CH;

[0113] e1 is independently selected from 0, 1, 2, 3 or 4; e2 is independently selected from 0, 1, 2 or 3; e3 is independently selected from 0, 1 or 2; e4 is independently selected from 0, 1, 2, 3, 4, 5 or 6; e5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0114] More preferably, L1, L2, L3, L4 are independently selected from a single bond or any one of the following groups:

[0115]

[0116]

[0117] The R 13 is independently selected from hydrogen, deuterium, halogen, trifluoromethyl, cyano, or substituted or unsubstituted of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, camphenyl, norbornyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, triphenylenyl, perylenyl, pyrenyl, group, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, fluorenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, acridinyl, o-phenanthrolinyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl;

[0118] The R 14Independently selected from hydrogen, deuterium, trifluoromethyl or a substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bornanyl, norbornyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, perylenyl, pyrenyl, group, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, fluorenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, acridinyl, phenanthrolinyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl;

[0119] Said R 15 and R 16 are independently selected from hydrogen, deuterium, halogen, trifluoromethyl, cyano, or a substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bornanyl, norbornyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, perylenyl, pyrenyl, group, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, fluorenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, acridinyl, phenanthrolinyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl;

[0120] Said e0 is independently selected from 0 or 1; said e1 is independently selected from 0, 1, 2, 3 or 4; said e2 is independently selected from 0, 1, 2 or 3; said e3 is independently selected from 0, 1 or 2; said e4 is independently selected from 0, 1, 2, 3, 4, 5 or 6; said e5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said e6 is independently selected from 0, 1, 2, 3, 4 or 5; said e7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said e8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14;

[0121] Said R 13 to R 16In the “substituted or unsubstituted”, the substituents are independently selected from one or more of deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, deuterated tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, camphenyl, norbornyl, phenyl, deuterated phenyl. When there are multiple substituents, the multiple substituents are the same or different from each other.

[0122] Preferably, the heterocyclic compound is selected from any one of the following structures:

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148] The above only lists some specific structural forms of the heterocyclic compound shown in Formula 1, but the present invention is not limited to the listed chemical structures. All those based on Formula 1 with substituents defined as above should be included.

[0149] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode and an organic layer. The organic layer is located between the anode and the cathode or outside at least one of the anode and the cathode. It is characterized in that the organic layer comprises at least one of a hole transport layer or a cover layer, and at least one of the hole transport layer or the cover layer comprises at least one of the heterocyclic compounds of the present invention.

[0150] As the organic layer of the present invention, it can have a single-layer structure and a multi-layer structure. The single-layer structure includes a single layer containing a single material or a single layer containing multiple materials; the multi-layer structure includes multiple layers containing multiple materials. Specifically, the hole transport layer can comprise a first hole transport layer and a second hole transport layer, and the electron transport layer can comprise a first electron transport layer and a second electron transport layer; specifically, the materials for each organic functional layer can be selected from inorganic materials, organic materials or inorganic-organic materials formed by mixing the two, etc., but not limited thereto.

[0151] As the organic layer of the present invention, it includes a hole transport region, a light-emitting layer, an electron transport region and a cover layer. The hole transport region comprises functional layers such as a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting auxiliary layer, etc. The electron transport region comprises functional layers such as a hole blocking layer, an electron transport layer, an electron injection layer, etc. The organic functional layers can be increased or decreased according to actual needs.

[0152] Preferably, the organic layer is located between the anode and the cathode, the organic layer comprises a hole transport layer, and the hole transport layer comprises at least one of the heterocyclic compounds of the present invention.

[0153] Preferably, the organic layer is located outside one or more of the anode and the cathode, and the organic layer includes a covering layer, and the covering layer includes at least one heterocyclic compound of the present invention.

[0154] More preferably, the organic layer is located outside the cathode, and the organic layer includes a covering layer, and the covering layer includes at least one heterocyclic compound of the present invention.

[0155] As the anode material of the present invention, a material with a high work function is preferably used. The anode can be a transmissive electrode, a reflective electrode, or a semi-transmissive electrode. When the anode is a transmissive electrode, the material used to form the anode can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof; when the anode is a semi-transmissive electrode or a reflective electrode, the material used to form the anode can be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof. The anode can have a single-layer structure or a multi-layer structure including two or more layers. For example, the anode can have a single-layer structure of Al or a three-layer structure of ITO / Ag / ITO, but the structure of the anode is not limited thereto.

[0156] As the hole injection layer material of the present invention, a material with good hole acceptance ability is preferably used. It can be selected from any one or more of the following structures: metal porphyrin, oligothiophene, arylamine derivative, perylene derivative, hexanitrile hexaazatriphenylene compound, quinacridone compound, anthraquinone compound, and conductive polymers based on polyaniline and polythiophene, etc., but not limited thereto.

[0157] As the hole transport layer material of the present invention, a material with a high hole mobility is preferably used. In addition to the heterocyclic compounds of the present invention, it can also be selected from any one or more of the following structures: carbazole derivative, triarylamine derivative, biphenyldiamine derivative, fluorene derivative, stilbene derivative, phthalocyanine compound, hexanitrile hexaazatriphenylene compound, quinacridone compound, anthraquinone compound, polyaniline, polythiophene, polyvinylcarbazole, etc., but not limited thereto. Preferably, the heterocyclic compounds of the present invention are used as the hole transport layer material.

[0158] As the luminescent layer material of the present invention, it may only contain the guest material, or may adopt the form of the guest material dispersed in the host material, and two host materials may be used to form a double host material. The host material of the luminescent layer not only needs to have bipolar charge transport properties, but also requires appropriate energy levels to effectively transfer the excitation energy to the guest luminescent material. Examples of such materials include stilbenyl aryl derivatives, stilbene derivatives, carbazole derivatives, triarylamine derivatives, anthracene derivatives, pyrene derivatives, etc. The guest material can be selected from any one or several of the following structures: metal complexes (such as iridium complexes, platinum complexes, osmium complexes, rhodium complexes, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives, etc., but not limited thereto.

[0159] As the electron injection layer material of the present invention, a material with a low work function is preferably used. It can be selected from any one or more of the following structures: alkali metals, alkaline earth metals, halides of alkali metals, halides of alkaline earth metals, oxides of alkali metals, oxides of alkaline earth metals, alkali metal salts, alkaline earth metal salts, and other substances with high electron injection properties. Examples can include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, etc., but not limited thereto.

[0160] As the electron transport layer material of the present invention, a material with a high electron mobility is preferably used. It can be selected from any one or several of the following structures: metal chelates, oxazole derivatives, thiazole derivatives, diazole derivatives, azobenzene derivatives, phenazine derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, quinoline derivatives, phenanthroline derivatives, benzimidazole derivatives, etc., but not limited thereto.

[0161] As the hole blocking layer of the present invention, a material with excellent hole blocking ability is preferably used. The material used is required to have a T1 energy level higher than that of the luminescent layer, so as to block the energy loss of the luminescent layer. In addition, the HOMO energy level of the selected material should be lower than that of the host material of the luminescent layer to play a role in blocking holes. Further, the electron mobility of the hole blocking layer material used is above 10 -6 cm 2 / Vs, which is beneficial to the transport of electrons. Triazine derivatives, azobenzene derivatives, etc. are preferably used.

[0162] As the cathode material of the present invention, a material with a low work function is preferably used. The cathode can be selected from a transmissive electrode, a semi-reflective electrode, or a reflective electrode. When the cathode is a transmissive electrode, the material used to form the cathode can be selected from transparent metal oxides (e.g., ITO, IZO, etc.); when the cathode is a semi-reflective electrode or a reflective electrode, the material used to form the cathode can be selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds including them, or mixtures thereof (e.g., a mixture of Ag and Mg), but not limited thereto.

[0163] As the capping layer material of the present invention, a material with high light extraction efficiency is preferably used. In addition to the heterocyclic compounds described in the present invention, any one or more of the following structures can also be selected: for example, it can be metal halides, oxides, nitrides, oxynitrides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, arylamine compounds, etc., but not limited thereto. Preferably, the capping layer material uses the heterocyclic compounds described in the present invention.

[0164] Each of the above-mentioned cathode, anode, organic layer, and capping layer can be prepared by any one of methods such as vacuum evaporation, inkjet printing, sputtering, plasma, ion plating, spin coating, dipping, screen printing, etc. There is no special limitation on the film thickness of each layer, as long as good device performance can be obtained. Each of the above-mentioned organic layers is preferably prepared by vacuum evaporation, inkjet printing, or spin coating.

[0165] The thickness of each of the above-mentioned organic layers and the capping layer is usually 5 nm to 100 μm, preferably 10 nm to 200 nm. The thicknesses of the anode and the cathode are adjusted according to the required transparency.

[0166] The present invention also provides a preparation method of the heterocyclic compound shown in Formula 1, but the preparation method of the present invention is not limited thereto, and the following is only an example of the synthesis route. All the following synthesis routes adopt the reaction types commonly used in organic synthesis, and there is no special limitation on the reaction conditions (e.g., the selection, dosage, addition sequence, and method of reaction solvents, catalysts, ligands, bases, etc.), and conventional methods and operations can be used.

[0167] When Ar1 and Ar2 are the same, the synthesis route of the heterocyclic compound shown in Formula 1:

[0168]

[0169] Xa, Xb, Xc, and Xd are independently selected from any one of Cl, Br, and I.

[0170] When Ar1 and Ar2 are different, the synthesis route of the heterocyclic compound shown in Formula 1:

[0171]

[0172] Xe, Xf, Xg, and Xh are independently selected from any one of Cl, Br, and I.

[0173] When Ar2 is hydrogen and L2 is a single bond, the synthetic route of the heterocyclic compound shown in Formula 1:

[0174]

[0175] Xi, Xj, and Xk are independently selected from any one of Cl, Br, and I.

[0176] The present invention is more specifically explained by the following examples, and the technical solutions and technical effects of the present invention are further described, but it is not intended to limit the present invention thereby. Based on this description, those of ordinary skill in the art will be able to practice the present invention and prepare other compounds and devices according to the present invention without creative efforts within the entire scope disclosed.

[0177] Description of raw materials, reagents, and characterization equipment:

[0178] The present invention has no particular limitation on the sources of the raw materials used in the following examples, and commercially available product raw materials can be used or prepared by methods well-known to those skilled in the art.

[0179] Mass spectrometry was performed using a Waters G2-Si quadrupole time-of-flight high-resolution mass spectrometer from the UK, with chloroform as the solvent;

[0180] Elemental analysis was performed using a VarioELcube type organic elemental analyzer from Elementar of Germany, with a sample mass of 5 - 10 mg.

[0181] [Synthesis Example 1] Synthesis of Compound 7

[0182]

[0183] Preparation of Intermediate d-7:

[0184] Under nitrogen protection, toluene (150 mL), e-7 (50.00 mmol, 14.86 g), f-7 (50.00 mmol, 4.66 g), palladium acetate (0.60 mmol, 0.17 g), sodium tert-butoxide (100.00 mmol, 9.61 g) and tri-tert-butylphosphine (3.00 mmol, 0.61 g) were added to the reaction bottle in sequence, and the mixture was stirred and refluxed for 3.5 h. After the reaction was completed, it was cooled to room temperature, water was added, extracted with ethyl acetate, the organic phase was dried with anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized with toluene / methanol = 5:1 to obtain d-7 (12.07 g, yield 78%), and the solid purity was 99.69% by HPLC. Mass spectrum m / z: 309.1167 (theoretical value: 309.1154).

[0185] Preparation of intermediate A-7:

[0186] Under nitrogen protection, a-7 (70.00 mmol, 22.75 g), b-7 (140.00 mmol, 34.17 g), tetrakistriphenylphosphine palladium (1.40 mmol, 1.62 g), potassium carbonate (280.00 mmol, 38.70 g), 200 mL toluene, 100 mL ethanol, 100 mL water were added to the reaction bottle in sequence, and the mixture was stirred and refluxed for 4 h. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic layer was dried with anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized with toluene / ethanol = 5:1 to obtain A-7 (20.97 g, yield 75%), and the solid purity was 99.75% by HPLC. Mass spectrum m / z: 399.1272 (theoretical value: 399.1259).

[0187] Preparation of intermediate B-7:

[0188] Under nitrogen protection, toluene (150 mL), A-7 (50.00 mmol, 19.97 g), c-7 (50.00 mmol, 9.57 g), palladium acetate (0.75 mmol, 0.17 g), sodium tert-butoxide (100.00 mmol, 9.61 g) and tri-tert-butylphosphine (3.00 mmol, 0.61 g) were added to the reaction bottle in sequence, and the mixture was stirred and refluxed for 5 h. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized with toluene / methanol = 10:1 to obtain B-7 (18.36 g, yield 72%), and the solid purity was 99.81% by HPLC. Mass spectrum m / z: 509.1170 (theoretical value: 509.1183).

[0189] Preparation of compound 7:

[0190] Under nitrogen protection, toluene (100 mL), B-7 (30.00 mmol, 15.30 g), d-7 (30.00 mmol, 9.28 g), tridibenzylideneacetone dipalladium (0.30 mmol, 0.27 g), sodium tert-butoxide (60.00 mmol, 5.77 g) and tri-tert-butylphosphine (1.80 mmol, 0.37 g) were added to the reaction bottle in sequence, and the mixture was stirred and refluxed for 6 h. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized from toluene to obtain compound 7 (15.97 g, yield 68%). The solid purity was 99.95% by HPLC. Mass spectrum m / z: 782.2583 (theoretical value: 782.2569). Theoretical element content (%) C 56 H 34 N2O3: C, 85.91; H, 4.38; N, 3.58. Measured element content (%): C, 85.95; H, 4.35; N, 3.61.

[0191] [Synthesis Example 2] Synthesis of Compound 46

[0192]

[0193] According to the preparation method of Synthesis Example 1, c-7 and d-7 were replaced by equimolar c-46 and d-46, respectively, to obtain compound 46 (18.29 g). The solid purity was ≥ 99.92% as determined by HPLC. Mass spectrum m / z: 870.3257 (theoretical value: 870.3246). Theoretical element content (%) C 64 H 42 N2O2: C, 88.25; H, 4.86; N, 3.22. Measured element content (%): C, 88.22; H, 4.82; N, 3.25.

[0194] [Synthesis Example 3] Synthesis of Compound 56

[0195]

[0196] According to the preparation method of Synthesis Example 1, b-7, c-7, and d-7 were replaced by equimolar amounts of b-56, c-56, and d-56, respectively, to obtain compound 56 (16.79 g). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 822.3169 (theoretical value: 822.3184). Theoretical element content (%) C 60 H 34D4N2O2: C, 87.56; H, 5.14; N, 3.40. Measured elemental content (%): C, 87.59; H, 5.15; N, 3.34.

[0197] [Synthesis Example 4] Synthesis of Compound 76

[0198]

[0199] According to the preparation method of Synthesis Example 1, replace e-7, f-7, b-7, c-7, d-7 with equimolar e-76, f-76, b-76, c-46, d-76 respectively, to obtain Compound 76 (19.23 g), and the solid purity detected by HPLC is ≥99.93%. Mass spectrometry m / z: 970.3550 (theoretical value: 970.3559). Theoretical elemental content (%) C 72 H 46 N2O2: C, 89.05; H, 4.77; N, 2.88. Measured elemental content (%): C, 89.02; H, 4.72; N, 2.91.

[0200] [Synthesis Example 5] Synthesis of Compound 84

[0201]

[0202]

[0203] According to the preparation method of Synthesis Example 1, replace e-7, c-7, d-7 with equimolar e-84, c-84, d-84 respectively, to obtain Compound 84 (18.08 g), and the solid purity detected by HPLC is ≥99.97%. Mass spectrometry m / z: 926.3861 (theoretical value: 926.3872). Theoretical elemental content (%) C 68 H 50 N2O2: C, 88.09; H, 5.44; N, 3.02. Measured elemental content (%): C, 88.05; H, 5.48; N, 3.05.

[0204] [Synthesis Example 6] Synthesis of Compound 139

[0205]

[0206] Preparation of Intermediate C-139:

[0207] Under nitrogen protection, a-139 (100.00mmol, 28.05g), b-139 (100.00mmol, 26.91g), tetrakistriphenylphosphine palladium (1.00mmol, 1.16g), sodium carbonate (200.00mmol, 21.20g), 300mL toluene, 150mL ethanol, 150mL water were added to the reaction bottle in sequence, and the mixture was stirred and refluxed for 3h. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic layer was dried with anhydrous magnesium sulfate, filtered, the solvent was removed, and recrystallized with toluene / ethanol = 5:1 to obtain C-139 (26.05g, yield 76%), and the solid purity was 99.69% by HPLC. Mass spectrum m / z: 342.0543 (theoretical value: 342.0560).

[0208] Preparation of intermediate D-139:

[0209] Under nitrogen protection, C-139 (70.00 mmol, 23.99 g), b-46 (70.00 mmol, 17.09 g), tetrakistriphenylphosphine palladium (0.70 mmol, 0.81 g), potassium carbonate (140.00 mmol, 19.35 g), 200 mL toluene, 100 mL ethanol, 100 mL water were added to the reaction bottle in sequence, and the mixture was stirred and refluxed for 4 h. After the reaction was completed, it was cooled to room temperature, water was added, and it was extracted with dichloromethane. The organic layer was dried with anhydrous magnesium sulfate, filtered, the solvent was removed, and it was recrystallized with toluene / ethanol = 10:1 to obtain D-139 (21.99 g, yield 74%). The solid purity was 99.76% by HPLC. Mass spectrum m / z: 424.1203 (theoretical value: 424.1212).

[0210] Preparation of intermediate E-139:

[0211] Under nitrogen protection, toluene (150 mL), D-139 (50.00 mmol, 21.22 g), c-139 (50.00 mmol, 13.78 g), palladium acetate (0.75 mmol, 0.17 g), sodium tert-butoxide (100.00 mmol, 9.61 g) and tri-tert-butylphosphine (3.00 mmol, 0.61 g) were added to the reaction bottle in sequence, and the mixture was stirred and refluxed for 5 h. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized with toluene / methanol = 10:1 to obtain E-139 (22.60 g, yield 73%), and the solid purity was 99.82% by HPLC. Mass spectrum m / z: 618.1968 (theoretical value: 618.1950).

[0212] Preparation of compound 139:

[0213] Under nitrogen protection, toluene (100 mL), E-139 (30.00 mmol, 18.57 g), d-139 (30.00 mmol, 5.08 g), tridibenzylideneacetone dipalladium (0.30 mmol, 0.27 g), sodium tert-butoxide (60.00 mmol, 5.77 g) and tri-tert-butylphosphine (1.80 mmol, 0.37 g) were added to the reaction bottle in sequence, and the mixture was stirred and refluxed for 6 h. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized from toluene to obtain compound 139 (15.79 g, yield 70%). The solid purity was ≥99.93% detected by HPLC. Mass spectrum m / z: 751.3089 (theoretical value: 751.3075). Theoretical element content (%) C 53 H 25 D8N3O2: C, 84.66; H, 5.49; N, 5.59. Measured element content (%): C, 84.62; H, 5.53; N, 5.56.

[0214] [Synthesis Example 7] Synthesis of Compound 168

[0215]

[0216] According to the preparation method of Synthesis Example 1, a-7, c-7, and d-7 were replaced by equimolar a-168, c-168, and d-168, respectively, to obtain compound 168 (16.33 g). The solid purity was ≥ 99.91% as determined by HPLC. Mass spectrum m / z: 788.2385 (theoretical value: 788.2399). Theoretical element content (%) C 51 H 31 F3N4O2: C, 77.65; H, 3.96; N, 7.10. Measured element content (%): C, 77.68; H, 3.91; N, 7.13.

[0217] [Synthesis Example 8] Synthesis of Compound 173

[0218]

[0219] Preparation of intermediate i-173:

[0220] Under nitrogen protection, g-173 (230.00 mmol, 45.32 g), h-173 (230.00 mmol, 35.97 g), tetrakis(triphenylphosphine)palladium(0) (2.30 mmol, 2.66 g), sodium carbonate (460.00 mmol, 48.76 g), 500 mL of toluene, 250 mL of ethanol, and 250 mL of water were successively added to the reaction flask. The mixture was stirred and refluxed for 4 h. After the reaction was completed, it was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallization was carried out with toluene / ethanol = 5:1 to obtain i-173 (39.97 g, yield 76%). The purity of the solid was detected by HPLC to be 99.69%. Mass spectrometry m / z: 228.0355 (theoretical value: 228.0342).

[0221] Preparation of intermediate b-173:

[0222] Under nitrogen protection, intermediate i-173 (170.00 mmol, 38.87 g), B2Pin2 (187.00 mmol, 47.49 g), potassium carbonate (340.00 mmol, 46.99 g), tetrakis(triphenylphosphine)palladium(0) (2.06 mmol, 2.38 g), and DMF (900 mL) were successively added to the reaction flask. The mixture was stirred and the above system was heated to reflux for 5 h. After the reaction was completed, it was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and recrystallization was carried out with toluene:ethanol = 5:1 to obtain b-173 (46.27 g, yield 85%). HPLC purity ≥ 99.74%. Mass spectrometry m / z: 320.1574 (theoretical value: 320.1584).

[0223] Preparation of compound 173:

[0224] According to the preparation method of Synthesis Example 1, b-7, c-7, and d-7 were respectively replaced with equimolar amounts of b-173, c-173, and d-139 to obtain compound 173 (18.24 g). The purity of the solid was detected by HPLC to be ≧ 99.94%. Mass spectrometry m / z: 906.3047 (theoretical value: 906.3058). Theoretical elemental content (%) C 64 H 40 F2N2O2: C, 84.75; H, 4.45; N, 3.09. Measured elemental content (%): C, 84.72; H, 4.49; N, 3.04.

[0225] [Synthesis Example 9] Synthesis of compound 180

[0226]

[0227] Preparation of Intermediate b-180:

[0228] According to the preparation method of Intermediate b-173 in Synthesis Example 8, replace g-173 and h-173 with equimolar g-180 and h-180 respectively to obtain Intermediate b-180 (45.86 g, yield 84%). The solid purity was detected by HPLC to be ≧99.72%. Mass spectrometry m / z: 321.1550 (theoretical value: 321.1536).

[0229] Preparation of Compound 180:

[0230] According to the preparation method of Synthesis Example 1, replace b-7, c-7, and d-7 with equimolar b-180, c-180, and d-180 respectively to obtain Compound 180 (18.40 g). The solid purity was detected by HPLC to be ≧99.97%. Mass spectrometry m / z: 928.3763 (theoretical value: 928.3777). Theoretical elemental content (%) C 66 H 48 N4O2: C, 85.32; H, 5.21; N, 6.03. Measured elemental content (%): C, 85.36; H, 5.25; N, 5.99.

[0231] [Synthesis Example 10] Synthesis of Compound 187

[0232]

[0233] According to the preparation method of Synthesis Example 1, replace a-7, c-7, and d-7 with equimolar a-187, c-187, and d-187 respectively to obtain Compound 187 (18.29 g). The solid purity was detected by HPLC to be ≧99.92%. Mass spectrometry m / z: 870.3258 (theoretical value: 870.3246). Theoretical elemental content (%) C 64 H 42 N2O2: C, 88.25; H, 4.86; N, 3.22. Measured elemental content (%): C, 88.27; H, 4.91; N, 3.19.

[0234] [Synthesis Example 11] Synthesis of Compound 195

[0235]

[0236] According to the preparation method of Synthesis Example 1, replace b-7, c-7, and d-7 with equimolar b-195, c-195, and d-195 respectively to obtain Compound 195 (17.49 g). The solid purity was detected by HPLC to be ≧99.98%. Mass spectrometry m / z: 869.3027 (theoretical value: 869.3042). Theoretical elemental content (%) C63 H 39 N3O2: C, 86.97; H, 4.52; N, 4.83. Measured elemental content (%): C, 86.92; H, 4.56; N, 4.86.

[0237] [Synthesis Example 12] Synthesis of Compound 199

[0238]

[0239] According to the preparation method of Synthesis Example 1, replace a-7, c-7, d-7 with equimolar amounts of a-199, c-199, d-199 respectively to obtain Compound 199 (16.94 g), and the solid purity detected by HPLC is ≧99.94%. Mass spectrometry m / z: 868.3081 (theoretical value: 868.3090). Theoretical elemental content (%) C 64 H 40 N2O2: C, 88.45; H, 4.64; N, 3.22. Measured elemental content (%): C, 88.41; H, 4.66; N, 3.26.

[0240] [Synthesis Example 13] Synthesis of Compound 212

[0241]

[0242] According to the preparation method of Synthesis Example 1, replace e-7, a-7, c-7, d-7 with equimolar amounts of e-212, a-212, c-212, d-212 respectively to obtain Compound 212 (17.63 g), and the solid purity detected by HPLC is ≧99.96%. Mass spectrometry m / z: 876.3708 (theoretical value: 876.3716). Theoretical elemental content (%) C 64 H 48 N2O2: C, 87.64; H, 5.52; N, 3.19. Measured elemental content (%): C, 87.61; H, 5.56; N, 3.17.

[0243] [Synthesis Example 14] Synthesis of Compound 229

[0244]

[0245] According to the preparation method of Synthesis Example 1, replace b-7, c-7, d-7 with equimolar amounts of b-229, c-229, d-139 respectively to obtain Compound 229 (17.52 g%), and the solid purity detected by HPLC is ≧99.93%. Mass spectrometry m / z: 884.3052 (theoretical value: 884.3039). Theoretical elemental content (%) C 64 H 40N2O3: C, 86.86; H, 4.56; N, 3.17. Measured elemental content (%): C, 86.81; H, 4.59; N, 3.19.

[0246] [Synthesis Example 15] Synthesis of Compound 234

[0247]

[0248] According to the preparation method of Synthesis Example 1, replace a-7, c-7, and d-7 with equimolar amounts of a-234, c-234, and d-234 respectively to obtain Compound 234 (18.03 g). The solid purity detected by HPLC is ≥99.91%. Mass spectrometry m / z: 870.4074 (theoretical value: 870.4092). Theoretical elemental content (%) C 63 H 42 D6N2O2: C, 86.86; H, 6.25; N, 3.22. Measured elemental content (%): C, 86.81; H, 6.29; N, 3.25.

[0249] [Synthesis Example 16] Synthesis of Compound 274

[0250]

[0251] According to the preparation method of Synthesis Example 1, replace e-7, f-7, c-7, and d-7 with equimolar amounts of g-173, f-274, c-274, and d-274 respectively to obtain Compound 274 (15.26 g). The solid purity detected by HPLC is ≥99.93%. Mass spectrometry m / z: 726.2469 (theoretical value: 726.2457). Theoretical elemental content (%) C 50 H 26 D4N2O4: C, 82.63; H, 4.71; N, 3.85. Measured elemental content (%): C, 82.61; H, 4.75; N, 3.82.

[0252] [Synthesis Example 17] Synthesis of Compound 277

[0253]

[0254] Preparation of Intermediate A-277:

[0255] Under nitrogen protection, a-277 (70.00mmol, 21.16g), b-277 (70.00mmol, 25.92g), tetrakistriphenylphosphine palladium (0.70mmol, 0.81g), potassium carbonate (140.00mmol, 19.35g) and 200mL toluene, 100mL ethanol, 100mL water were added to the reaction bottle in sequence, and the mixture was stirred and refluxed for 3.5h. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic layer was dried with anhydrous magnesium sulfate, filtered, the solvent was removed, and recrystallized with toluene / ethanol = 5:1 to obtain A-277 (24.12g, yield 74%), and the solid purity was 99.76% by HPLC. Mass spectrum m / z: 465.2079 (theoretical value: 465.2093).

[0256] Preparation of intermediate B-277:

[0257] Under nitrogen protection, toluene (150 mL), A-277 (50.00 mmol, 23.28 g), c-277 (50.00 mmol, 9.57 g), palladium acetate (0.75 mmol, 0.17 g), sodium tert-butoxide (100.00 mmol, 9.61 g) and tri-tert-butylphosphine (3.00 mmol, 0.61 g) were added to the reaction bottle in sequence, and the mixture was stirred and refluxed for 4.5 h. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized with toluene / methanol = 10:1 to obtain B-277 (20.70 g, yield 72%), and the solid purity was 99.86% by HPLC. Mass spectrum m / z: 575.2034 (theoretical value: 575.2016).

[0258] Preparation of compound 277:

[0259] Under nitrogen protection, toluene (100 mL), B-277 (30.00 mmol, 17.25 g), d-277 (30.00 mmol, 9.64 g), tridibenzylideneacetone dipalladium (0.30 mmol, 0.27 g), sodium tert-butoxide (60.00 mmol, 5.77 g) and tri-tert-butylphosphine (1.80 mmol, 0.37 g) were added to the reaction bottle in sequence, and the mixture was stirred and refluxed for 6 h. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized from toluene to obtain compound 277 (17.03 g, yield 66%). The solid purity was ≥99.95% detected by HPLC. Mass spectrum m / z: 860.3759 (theoretical value: 860.3767). Theoretical element content (%) C 64 H 48N2O: C, 89.27; H, 5.62; N, 3.25. Measured elemental content (%): C, 89.24; H, 5.66; N, 3.28.

[0260] [Synthesis Example 18] Synthesis of Compound 284

[0261]

[0262] Preparation of Intermediate d-284:

[0263] According to the preparation method of Intermediate d-7 in Synthesis Example 1, replace e-7 with an equimolar amount of i-173 to obtain Intermediate d-284 (10.27 g, yield 72%), and the solid purity detected by HPLC is ≥99.67%. Mass spectrometry m / z: 285.1167 (theoretical value: 285.1154).

[0264] Preparation of Compound 284:

[0265] According to the preparation method of Synthesis Example 17, replace a-277, b-277, c-277, d-277 with equimolar amounts of a-284, b-7, c-46, d-284 respectively to obtain Compound 284 (15.10 g), and the solid purity detected by HPLC is ≥99.97%. Mass spectrometry m / z: 718.2630 (theoretical value: 718.2620). Theoretical elemental content (%) C 52 H 34 N2O2: C, 86.88; H, 4.77; N, 3.90. Measured elemental content (%): C, 86.83; H, 4.74; N, 3.93.

[0266] [Synthesis Example 19] Synthesis of Compound 291

[0267]

[0268] Preparation of Intermediate b-291:

[0269] According to the preparation method of Intermediate b-173 in Synthesis Example 8, replace h-173 with an equimolar amount of h-291 to obtain Intermediate b-291 (46.85 g, yield 85%), and the solid purity detected by HPLC is ≥99.75%. Mass spectrometry m / z: 324.1821 (theoretical value: 324.1835).

[0270] Preparation of Intermediate d-291:

[0271] According to the preparation method of intermediate d-7 in Synthesis Example 1, e-7 was replaced with an equimolar amount of e-291 to obtain intermediate d-291 (10.31 g, yield 72%), and the solid purity detected by HPLC was ≧99.69%. Mass spectrometry m / z: 286.1123 (theoretical value: 286.1106).

[0272] Preparation of Compound 291:

[0273] According to the preparation method of Synthesis Example 17, a-277, b-277, c-277, and d-277 were respectively replaced with equimolar amounts of a-291, b-291, c-46, and d-291 to obtain Compound 291 (16.08 g), and the solid purity detected by HPLC was ≧99.94%. Mass spectrometry m / z: 799.3147 (theoretical value: 799.3137). Theoretical elemental content (%) C 57 H 33 D4N3O2: C, 85.58; H, 5.17; N, 5.25. Measured elemental content (%): C, 85.54; H, 5.13; N, 5.28.

[0274] [Synthesis Example 20] Synthesis of Compound 298

[0275]

[0276] Preparation of intermediate b-298:

[0277] According to the preparation method of intermediate b-173 in Synthesis Example 8, h-173 was replaced with an equimolar amount of h-298 to obtain intermediate b-298 (53.50 g, yield 85%), and the solid purity detected by HPLC was ≧99.69%. Mass spectrometry m / z: 370.1752 (theoretical value: 370.1740).

[0278] Preparation of intermediate d-298:

[0279] According to the preparation method of intermediate d-7 in Synthesis Example 1, e-7 was replaced with an equimolar amount of e-298 to obtain intermediate d-298 (11.24 g, yield 67%), and the solid purity detected by HPLC was ≧99.72%. Mass spectrometry m / z: 335.1325 (theoretical value: 335.1310).

[0280] Preparation of Compound 298:

[0281] According to the preparation method of Synthesis Example 17, replace a-277, b-277, c-277, and d-277 with equimolar amounts of a-284, b-298, c-46, and d-298 respectively to obtain Compound 298 (17.45 g), and the solid purity detected by HPLC is ≥99.96%. Mass spectrometry m / z: 894.3231 (theoretical value: 894.3246). Theoretical elemental content (%) C 66 H 42 N2O2: C, 88.57; H, 4.73; N, 3.13. Measured elemental content (%): C, 88.53; H, 4.76; N, 3.17.

[0282] [Synthesis Example 21] Synthesis of Compound 303

[0283]

[0284] Preparation of Intermediate b-303:

[0285] According to the preparation method of Intermediate b-173 in Synthesis Example 8, replace h-173 with an equimolar amount of h-303 to obtain Intermediate b-303 (46.01 g, yield 84%), and the solid purity detected by HPLC is ≥99.75%. Mass spectrometry m / z: 322.1473 (theoretical value: 322.1489).

[0286] Preparation of Intermediate d-303:

[0287] According to the preparation method of Intermediate d-7 in Synthesis Example 1, replace e-7 and f-7 with equimolar amounts of e-303 and f-303 respectively to obtain Intermediate d-303 (12.47 g, yield 69%), and the solid purity detected by HPLC is ≥99.78%. Mass spectrometry m / z: 361.1845 (theoretical value: 361.1830).

[0288] Preparation of Compound 303:

[0289] According to the preparation method of Synthesis Example 17, replace a-277, b-277, c-277, and d-277 with equimolar amounts of a-303, b-303, c-303, and d-303 respectively to obtain Compound 303 (17.56 g), and the solid purity detected by HPLC is ≥99.92%. Mass spectrometry m / z: 886.3660 (theoretical value: 886.3672). Theoretical elemental content (%) C 64 H 46 N4O: C, 86.65; H, 5.23; N, 6.32. Measured elemental content (%): C, 86.70; H, 5.19; N, 6.34.

[0290] [Synthesis Example 22] Synthesis of Compound 316

[0291]

[0292] Preparation of Intermediate d-316:

[0293] According to the preparation method of Intermediate d-7 in Synthesis Example 1, replace e-7 with an equimolar amount of e-316 to obtain Intermediate d-316 (7.61 g, yield 71%). The purity of the solid detected by HPLC is ≥99.73%. Mass spectrometry m / z: 214.1140 (theoretical value: 214.1154).

[0294] Preparation of Compound 316:

[0295] According to the preparation method of Synthesis Example 17, replace a-277, b-277, c-277, and d-277 with equimolar amounts of a-284, b-316, c-316, and d-316 respectively to obtain Compound 316 (15.26 g). The purity of the solid detected by HPLC is ≥99.97%. Mass spectrometry m / z: 747.2925 (theoretical value: 747.2934). Theoretical elemental content (%) C 54 H 29 D5N2O2: C, 86.72; H, 5.25; N, 3.75. Measured elemental content (%): C, 86.76; H, 5.22; N, 3.72.

[0296] [Synthesis Example 23] Synthesis of Compound 326

[0297]

[0298] According to the preparation method of Synthesis Example 17, replace a-277, b-277, c-277, and d-277 with equimolar amounts of a-326, b-7, c-326, and d-326 respectively to obtain Compound 326 (16.15 g). The purity of the solid detected by HPLC is ≥99.94%. Mass spectrometry m / z: 768.3029 (theoretical value: 768.3020). Theoretical elemental content (%) C 54 H 24 D 10 N2OS: C, 84.34; H, 5.77; N, 3.64. Measured elemental content (%): C, 84.29; H, 5.81; N, 3.63.

[0299] [Synthesis Example 24] Synthesis of Compound 330

[0300]

[0301] Preparation of Intermediate b-330:

[0302] According to the preparation method of intermediate b-173 in Synthesis Example 8, replace h-173 with an equimolar amount of h-330 to obtain intermediate b-330 (53.90 g, yield 83%). The solid purity detected by HPLC is ≥99.77%. Mass spectrometry m / z: 396.1882 (theoretical value: 396.1897).

[0303] Preparation of intermediate d-330:

[0304] According to the preparation method of intermediate d-7 in Synthesis Example 1, replace e-7 with an equimolar amount of e-330 to obtain intermediate d-330 (9.42 g, yield 71%). The solid purity detected by HPLC is ≥99.76%. Mass spectrometry m / z: 265.1478 (theoretical value: 265.1467).

[0305] Preparation of compound 330:

[0306] According to the preparation method of Synthesis Example 17, replace a-277, b-277, c-277, d-277 with equimolar amounts of a-330, b-330, c-330, d-330 respectively to obtain compound 330 (18.66 g). The solid purity detected by HPLC is ≥99.98%. Mass spectrometry m / z: 927.3840 (theoretical value: 927.3825). Theoretical elemental content (%) C 67 H 49 N3O2: C, 86.70; H, 5.32; N, 4.53. Measured elemental content (%): C, 86.67; H, 5.36; N, 4.50.

[0307] [Synthesis Example 25] Synthesis of compound 351

[0308]

[0309] Preparation of intermediate b-351:

[0310] According to the preparation method of intermediate b-173 in Synthesis Example 8, replace g-173 and h-173 with equimolar amounts of g-351 and h-351 respectively to obtain intermediate b-351 (52.52 g, yield 83%). The solid purity detected by HPLC is ≥99.73%. Mass spectrometry m / z: 372.1657 (theoretical value: 372.1645).

[0311] Preparation of intermediate d-351:

[0312] According to the preparation method of intermediate d-7 in Synthesis Example 1, e-7 was replaced with equimolar i-351 to obtain intermediate d-351 (11.13 g, yield 66%), and the solid purity detected by HPLC was ≥99.71%. Mass spectrometry m / z: 337.1201 (theoretical value: 337.1215).

[0313] Preparation of Compound 351:

[0314] According to the preparation method of Synthesis Example 17, a-277, b-277, c-277, and d-277 were respectively replaced with equimolar a-284, b-351, c-46, and d-351 to obtain Compound 351 (17.53 g), and the solid purity detected by HPLC was ≥99.96%. Mass spectrometry m / z: 898.3063 (theoretical value: 898.3056). Theoretical elemental content (%) C 62 H 38 N6O2: C, 82.83; H, 4.26; N, 9.35. Measured elemental content (%): C, 82.85; H, 4.22; N, 9.38.

[0315] [Synthesis Example 26] Synthesis of Compound 380

[0316]

[0317] According to the preparation method of Synthesis Example 1, e-7, b-7, c-7, and d-7 were respectively replaced with equimolar e-380, b-380, c-380, and d-380 to obtain Compound 380 (18.07 g), and the solid purity detected by HPLC was ≥99.91%. Mass spectrometry m / z: 898.3044 (theoretical value: 898.3056). Theoretical elemental content (%) C 62 H 38 N6O2: C, 82.83; H, 4.26; N, 9.35. Measured elemental content (%): C, 82.78; H, 4.29; N, 9.40.

[0318] [Synthesis Example 27] Synthesis of Compound 442

[0319]

[0320] According to the preparation method of Synthesis Example 1, e-7, b-7, c-7, and d-7 were respectively replaced with equimolar e-442, b-442, c-442, and d-442 to obtain Compound 442 (17.39 g), and the solid purity detected by HPLC was ≥99.93%. Mass spectrometry m / z: 827.2413 (theoretical value: 827.2429). Theoretical elemental content (%) C 57 H37 N3S2: C, 82.68; H, 4.50; N, 5.07. Measured elemental content (%): C, 82.65; H, 4.55; N, 5.11.

[0321] [Synthesis Example 28] Synthesis of Compound 588

[0322]

[0323] According to the preparation method of Synthesis Example 17, replace a-277, b-277, c-277, d-277 with equimolar amounts of a-588, b-588, c-46, d-588 respectively to obtain Compound 588 (17.25 g), and the solid purity detected by HPLC is ≧99.97%. Mass spectrometry m / z: 870.3056 (theoretical value: 870.3069). Theoretical elemental content (%) C 64 H 42 N2S: C, 88.24; H, 4.86; N, 3.22. Measured elemental content (%): C, 88.28; H, 4.82; N, 3.25.

[0324] [Synthesis Example 29] Synthesis of Compound 627

[0325]

[0326] Preparation of Intermediate d-627:

[0327] According to the preparation method of Intermediate d-7 in Synthesis Example 1, replace e-7, f-7 with equimolar amounts of e-627, f-627 to obtain Intermediate d-627 (14.29 g, yield 73%), and the solid purity detected by HPLC is ≧99.68%. Mass spectrometry m / z: 391.2312 (theoretical value: 391.2300).

[0328] Preparation of Compound 627:

[0329] According to the preparation method of Synthesis Example 17, replace a-277, b-277, c-277, d-277 with equimolar amounts of a-284, b-627, c-627, d-627 respectively to obtain Compound 627 (17.91 g), and the solid purity detected by HPLC is ≧99.92%. Mass spectrometry m / z: 864.3550 (theoretical value: 864.3538). Theoretical elemental content (%) C 63 H 48 N2S: C, 87.46; H, 5.59; N, 3.24. Measured elemental content (%): C, 87.42; H, 5.64; N, 3.21.

[0330] [Synthesis Example 30] Synthesis of Compound 642

[0331]

[0332] Preparation of Intermediate d-642:

[0333] According to the preparation method of Intermediate d-7 in Synthesis Example 1, replace e-7 with an equimolar amount of e-642 to obtain Intermediate d-642 (11.45 g, yield 76%). The purity of the solid detected by HPLC is ≥ 99.68%. Mass spectrometry m / z: 301.0937 (theoretical value: 301.0925).

[0334] Preparation of Compound 642:

[0335] According to the preparation method of Synthesis Example 17, replace a-277, b-277, c-277, and d-277 with equimolar amounts of a-284, b-642, c-642, and d-642 respectively to obtain Compound 642 (16.16 g). The purity of the solid detected by HPLC is ≥ 99.94%. Mass spectrometry m / z: 815.2441 (theoretical value: 815.2429). Theoretical elemental content (%) C 56 H 37 N3S2: C, 82.42; H, 4.57; N, 5.15. Measured elemental content (%): C, 82.45; H, 4.52; N, 5.20.

[0336] [Synthesis Example 31] Synthesis of Compound 645

[0337]

[0338] According to the preparation method of Synthesis Example 6, replace a-139, b-139, b-46, and c-139 with equimolar amounts of a-645, b-442, b-645, and c-645 respectively to obtain Compound 645 (16.85 g). The purity of the solid detected by HPLC is ≥ 99.98%. Mass spectrometry m / z: 825.2829 (theoretical value: 825.2814). Theoretical elemental content (%) C 58 H 39 N3OS: C, 84.34; H, 4.76; N, 5.09. Measured elemental content (%): C, 84.31; H, 4.75; N, 5.11.

[0339] [Synthesis Example 32] Synthesis of Compound 653

[0340]

[0341] Preparation of Intermediate d-653:

[0342] According to the preparation method of intermediate d-7 in Synthesis Example 1, replace e-7 with an equimolar amount of e-653 to obtain intermediate d-653 (9.88 g, yield 69%). The solid purity detected by HPLC is ≧99.70%. Mass spectrometry m / z: 286.1452 (theoretical value: 286.1470).

[0343] Preparation of Compound 653:

[0344] According to the preparation method of Synthesis Example 17, replace a-277, b-277, c-277, and d-277 with equimolar amounts of a-653, b-653, c-653, and d-653 respectively to obtain Compound 653 (17.18 g). The solid purity detected by HPLC is ≧99.93%. Mass spectrometry m / z: 817.3279 (theoretical value: 817.3288). Theoretical elemental content (%) for C57H35D5N4S: C, 83.69; H, 5.54; N, 6.85. Measured elemental content (%): C, 83.72; H, 5.52; N, 6.88.

[0345] [Device Example 1]

[0346] First, place the glass substrate coated with ITO / Ag / ITO in distilled water and wash it 2 times, ultrasonically wash it for 30 minutes, then wash it repeatedly with distilled water 2 times, ultrasonically wash it for 10 minutes. After the distilled water washing is completed, perform ultrasonic washing in sequence with isopropanol, acetone, and methanol solvents, and then dry it on a hot plate heated to 120 °C. Transfer the dried substrate to a plasma cleaner, wash it for 5 minutes, and then transfer the substrate to an evaporation machine.

[0347] Then, vacuum deposit HI-1 as a hole injection layer on the already cleaned ITO / Ag / ITO substrate with a deposition thickness of 10 nm. Vacuum deposit the compound 7 of the present invention as a hole transport layer on this hole injection layer with a deposition thickness of 110 nm. Vacuum deposit BH-1 as a host material and vacuum deposit BD-1 as a doping material (mass ratio 92:8) on the hole transport layer to form a light-emitting layer with a deposition thickness of 40 nm. Vacuum deposit ET-1 and Liq (mass ratio 1:1) as an electron transport layer on the light-emitting layer with a deposition thickness of 40 nm. On this electron transport layer, vacuum deposit LiF as an electron injection layer with a deposition thickness of 1 nm. Then, vacuum deposit Mg:Ag (mass ratio 1:9) as a cathode on this electron injection layer with a deposition thickness of 10 nm. Then, vacuum deposit CP-1 as a cover layer on the cathode with a deposition thickness of 70 nm, thereby preparing organic electroluminescent device 1.

[0348]

[0349] [Device Examples 2 - 32]

[0350] Use Compound 46, Compound 56, Compound 76, Compound 84, Compound 139, Compound 168, Compound 173, Compound 180, Compound 187, Compound 195, Compound 199, Compound 212, Compound 229, Compound 234, Compound 274, Compound 277, Compound 284, Compound 291, Compound 298, Compound 303, Compound 316, Compound 326, Compound 330, Compound 351, Compound 380, Compound 442, Compound 588, Compound 627, Compound 642, Compound 645, Compound 653 of the present invention to replace Compound 7 in Device Example 1 as the hole transport layer. Except for this, the other preparation steps are the same as those in Device Example 1 to prepare organic electroluminescent devices 2 - 32.

[0351] [Comparative Device Examples 1 - 2]

[0352] Use Comparative Compound 1 and Comparative Compound 2 to replace Compound 7 in Device Example 1 as the hole transport layer. Except for this, the other preparation steps are the same as those in Device Example 1 to prepare Comparative Devices 1 - 2.

[0353] A combined IVL test system consisting of test software, a computer, a K2400 digital source meter produced by Keithley Corporation in the United States, and a PR788 spectral scanning luminance meter of PhotoResearch Corporation in the United States is used to test the luminous efficiency of the organic electroluminescent device. The lifetime test is carried out using the M6000 OLED lifetime test system of McScience Corporation. The test environment is the atmospheric environment and the temperature is room temperature. The test results of the luminous characteristics of the organic electroluminescent devices obtained from Device Examples 1 - 32 and Comparative Examples 1 - 2 of the present invention are shown in Table 1 below.

[0354] [Table 1] Test of the Luminous Characteristics of Organic Electroluminescent Devices

[0355]

[0356]

[0357] It can be seen from the results in Table 1 that when the heterocyclic compounds of the present invention are applied to the organic light-emitting device as the hole transport layer, compared with Comparative Devices 1 - 2, the driving voltage of the organic electroluminescent device can be reduced, the luminous efficiency of the organic electroluminescent device can be improved, and the service life of the organic electroluminescent device can be extended.

[0358] [Device Example 33]

[0359] On the already cleaned ITO / Ag / ITO substrate, HI-1 is vacuum-evaporated as the hole injection layer with an evaporation thickness of 10 nm. On this hole injection layer, HT-1 of the present invention is vacuum-evaporated as the hole transport layer with an evaporation thickness of 100 nm. On the hole transport layer, RH-1 is vacuum-evaporated as the host material, and RD-1 is vacuum-evaporated as the doping material (mass ratio 92:8) to form the light-emitting layer with an evaporation thickness of 35 nm. On the light-emitting layer, ET-1 and Liq (mass ratio 1:1) are vacuum-evaporated as the electron transport layer with an evaporation thickness of 40 nm. On this electron transport layer, LiF is vacuum-evaporated as the electron injection layer with an evaporation thickness of 1 nm. Then, Mg:Ag (mass ratio 1:9) is vacuum-evaporated as the cathode on this electron injection layer with an evaporation thickness of 15 nm. Then, compound 7 of the present invention is vacuum-evaporated as the capping layer on the cathode with an evaporation thickness of 65 nm, thereby preparing the organic electroluminescent device 33.

[0360] [Device Examples 34 - 64]

[0361] Compound 46, compound 56, compound 76, compound 84, compound 139, compound 168, compound 173, compound 180, compound 187, compound 195, compound 199, compound 212, compound 229, compound 234, compound 274, compound 277, compound 284, compound 291, compound 298, compound 303, compound 316, compound 326, compound 330, compound 351, compound 380, compound 442, compound 588, compound 627, compound 642, compound 645, compound 653 of the present invention are used to replace compound 7 in Device Example 33 as the capping layer. Except for this, the other preparation steps are the same as those in Device Example 33, and organic electroluminescent devices 34 - 64 are prepared.

[0362] [Comparative Device Examples 3 - 4]

[0363] Comparative compound 3 and comparative compound 4 are used to replace compound 7 in Device Example 33 as the capping layer. Except for this, the other preparation steps are the same as those in Device Example 33, and comparative devices 3 - 4 are prepared.

[0364] For devices 33 - 64 in the device examples of the present invention and comparative examples 3 - 4, the test results of the light-emitting characteristics of the obtained organic electroluminescent devices are shown in Table 2 below.

[0365] [Table 2] Test of the Light-Emitting Characteristics of Organic Electroluminescent Devices

[0366]

[0367]

[0368] As can be seen from the results in Table 2, when the heterocyclic compound of the present invention is applied to an organic light-emitting device as a covering layer material, compared with Comparative Devices 3 to 4, it can effectively improve the light extraction efficiency of the device, thereby improving the luminous efficiency and service life of the device.

[0369] It should be noted that the present invention has been specifically described with individual embodiments. For those of ordinary skill in the art, without departing from the principle of the present invention, several improvements and modifications can still be made to the present invention, and these improvements and modifications also fall within the protection scope of the present invention.

Claims

1. A heterocyclic compound, characterized in that, The heterocyclic compound is represented by the structure shown in Formula 1: In Formula 1, R0 is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl; or a substituted or unsubstituted benzene ring is formed by connection between two adjacent R0; the substituent of "substituted or unsubstituted" in R0 is selected from deuterium; a0 is independently selected from 0, 1, 2, 3 or 4; Y is independently selected from N or CH; Y bonded to L1 or L2 is selected from C; and 0 or 1 of the four Ys in each six-membered ring is selected from N; L is selected from any one of the following groups: R9 is independently selected from hydrogen, deuterium, halogen, or substituted or unsubstituted: any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; The R 11 , R 12 independently selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; d1 is independently selected from 0, 1, 2, 3 or 4; d2 is independently selected from 0, 1, 2 or 3; d3 is independently selected from 0, 1 or 2; d4 is independently selected from 0, 1, 2, 3, 4, 5 or 6; d5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; The R9, R 11 , R 12 The substituent of "substituted or unsubstituted" is selected from deuterium; L1, L2, L3, L4 are independently selected from a single bond or any one of the following groups: The R 13 independently selected from hydrogen, deuterium, halogen, or any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; e1 is independently selected from 0, 1, 2, 3 or 4; e2 is independently selected from 0, 1, 2 or 3; e3 is independently selected from 0, 1 or 2; The R 13 The substituent of "substituted or unsubstituted" is selected from deuterium; Ar1 is selected from Formula 2; Ar2 is selected from hydrogen, Formula 2 or any one of the following groups: Ar3, Ar4 are independently selected from Formula 2 or any one of the following groups: R3 is independently selected from hydrogen, deuterium, trifluoromethyl, cyano, or substituted or unsubstituted: any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, adamantyl, phenyl, biphenyl, naphthyl; R4, R5, R6 are independently selected from substituted or unsubstituted: any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; R8 is independently selected from hydrogen, deuterium, or substituted or unsubstituted: any one of phenyl, biphenyl, naphthyl; X2 is selected from O or S; Z is independently selected from N or CH; c1 is independently selected from 0, 1, 2, 3, 4 or 5; c2 is independently selected from 0, 1, 2, 3 or 4; c3 is independently selected from 0, 1, 2 or 3; c4 is independently selected from 0, 1 or 2; c5 is independently selected from 0, 1, 2, 3, 4, 5 or 6; c6 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; c7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; c8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; c9 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; The substituent of "substituted or unsubstituted" in R3-R6, R8 is selected from deuterium; In Formula 2, X is selected from O or S; Y1 is independently selected from N or CH; and among the four Y1s in Formula 2, 0 or 1 Y1 is selected from N; R1 and R2 are independently selected from hydrogen, deuterium, cyano, or the following substituted or unsubstituted groups: any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, naphthyl; or two adjacent R1s are connected to form a substituted or unsubstituted benzene ring; a1 is selected from 0, 1, 2, 3 or 4; a2 is selected from 0, 1 or 2; The substituent of "substituted or unsubstituted" in R1 and R2 is selected from deuterium.

2. The heterocyclic compound according to claim 1, wherein The formula 2 in which R1 and R2 are independently selected from hydrogen, deuterium, or the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl.

3. The heterocyclic compound according to claim 1, wherein The formula 2 Any one selected from the following groups:

4. The heterocyclic compound according to claim 1, wherein Ar3 and Ar4 are independently selected from any one of Formula 2 or the following groups: R3 is independently selected from hydrogen, deuterium, or the following substituted or unsubstituted groups: any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; R5 and R6 are independently selected from or the following substituted or unsubstituted groups: any one of methyl; The substituent of "substituted or unsubstituted" in R3, R5 and R6 is selected from deuterium.

5. The heterocyclic compound according to claim 1, wherein L is selected from any one of the following groups:

6. A heterocyclic compound, wherein The heterocyclic compound is selected from any one of the following structures:

7. An organic electroluminescent device, comprising an anode, a cathode, and an organic layer, the organic layer being located between the anode and the cathode or outside at least one of the anode and the cathode, characterized in that, The organic layer includes at least one of a hole transport layer or a covering layer, and at least one of the hole transport layer or the covering layer contains at least one heterocyclic compound according to any one of claims 1 to 6.

Images