An organic electroluminescent device

Abstract

The present invention provides an organic electroluminescent device, and relates to the technical field of organic electroluminescent. The covering layer material contained in the organic electroluminescent device provided by the present invention has a high refractive index. When it is applied to the covering layer in the organic electroluminescent device, the light trapped in the device can be coupled out, the total reflection of light inside the device is reduced, the light extraction efficiency of the device is enhanced, and the luminous efficiency of the organic electroluminescent device is improved. At the same time, the covering layer material provided by the present invention also has a high glass transition temperature and good thermal stability, which can isolate water and oxygen in the air, avoid a sharp roll-off of the device efficiency, and thus prolong the service life of the organic electroluminescent device.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescence, and in particular relates to an organic electroluminescence device. Background Art

[0002] Organic Light-Emitting Diode (OLED) is a device driven by an external electric field. Holes and electrons are injected from the anode and cathode into the organic functional layer sandwiched between the two electrodes, and recombine in the light-emitting layer to form excitons, which transfer energy to the molecules of the organic light-emitting substance, causing them to be excited and transition from the ground state to the excited state. It has the advantages of light weight, fast response speed, wide operating temperature range, low energy consumption, high efficiency, and good color purity. It is widely used in many fields such as lighting and display, and is one of the most promising new display technologies.

[0003] OLED includes a cathode, an anode and an organic layer, and 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, etc. These organic layers play an important role in improving the driving voltage, luminous efficiency, color purity, service life and other performances of the OLED device. In order to improve the luminous efficiency and service life of the device, a covering layer can also be provided on the outside of at least one of the anode and the cathode.

[0004] According to the different paths of light transmission, OLED can be divided into bottom-emitting devices and top-emitting devices. In bottom-emitting devices, light is emitted from the substrate, the reflective electrode is above the organic light-emitting layer, and the transparent electrode is below the organic light-emitting layer. In the bottom-emitting device, part of the light in the device cannot pass through, and the light-emitting area becomes smaller; in the top-emitting device, the transparent electrode is on the organic light-emitting layer, and the reflective electrode is below the organic light-emitting layer, so the light is emitted from the opposite direction of the substrate, thereby increasing the light transmission area. At present, top-emitting devices are more widely used, and the light extraction efficiency of top-emitting devices is better than that of bottom-emitting devices. Top-emitting devices add a covering layer to the outside of the metal cathode, which can prevent the light emitted to the outside from being totally reflected and lost, and couple out the light trapped in the device, enhancing the light extraction efficiency, thereby improving the luminous efficiency of the device. Therefore, top-emitting devices have very good development prospects. However, the current top-emitting devices still have disadvantages such as low luminous efficiency and short service life.

[0005] In view of the current top-emitting devices having the disadvantages of low luminous efficiency and short service life, in order to continuously improve the performance of high-performance OLED devices, it is urgent to develop organic electroluminescent devices with excellent properties such as high luminous efficiency and long service life. Summary of the invention

[0006] In order to solve the above technical problems and improve the luminous efficiency and service life of OLED devices, the present invention provides an organic electroluminescent device, which includes a covering layer, which can effectively improve the light extraction efficiency of the device, thereby improving the luminous efficiency and service life of the OLED device. Specifically, the technical solution of the present invention is as follows:

[0007] An organic electroluminescent device comprises an anode, a cathode, an organic layer and a covering layer, wherein the covering layer is located outside at least one of the anode and the cathode, and is characterized in that the covering layer comprises a compound represented by Formula 1:

[0008]

[0009] The X is independently selected from N or CR a ;

[0010] The R a Any one independently selected from 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 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 R a They may be connected to form a substituted or unsubstituted ring;

[0011] The L is independently selected from any one of a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensing 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 group;

[0012] A and B are independently selected from Formula 2 or Formula 3, and at least one of A and B is selected from Formula 3;

[0013]

[0014] Ar is selected from any one of a substituted or unsubstituted C6-C30 aromatic group, a group formed by condensing 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 group;

[0015] The L a , L b Any one independently selected from 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 aliphatic ring, or a substituted or unsubstituted 5-30 membered heteroarylene group;

[0016] The Y is selected from O, S or NR p ;

[0017] The R p Any one independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0018] The X 1 Independently selected from N or CR c ;

[0019] The R b , R c Any one independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 5-30 membered heteroaryl; or two adjacent R c They may be connected to form a substituted or unsubstituted ring;

[0020] The b is selected from 0, 1 or 2.

[0021] Beneficial effects:

[0022] The covering layer material contained in the organic electroluminescent device provided by the present invention has a high refractive index. When applied to the organic electroluminescent device and used as a covering layer, the light trapped in the device can be effectively coupled out, the total reflection of light inside the device can be reduced, the light extraction efficiency of the device can be enhanced, and the luminous efficiency of the organic electroluminescent device can be improved; at the same time, the covering layer material provided by the present invention also has a high glass transition temperature and good thermal stability, can isolate water and oxygen in the air, and avoid a sharp drop in device efficiency, thereby achieving the effect of extending the service life of the organic electroluminescent device. DETAILED DESCRIPTION

[0023] The following will be clearly and completely described in conjunction with the technical solutions of the specific embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative work are within the scope of protection of the present invention.

[0024] In the compounds of the present invention, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes the atom in both its natural isotopic abundance and unnatural abundance.

[0025] The halogen atom mentioned in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0026] The alkyl group described in the present invention refers to a hydrocarbon group formed by missing a hydrogen atom in an alkane molecule, which can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 30 carbon atoms, 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 group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but not limited thereto; the branched-chain alkyl group includes 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., but not limited thereto. The above-mentioned alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl.

[0027] The cycloalkyl group of the present invention refers to a hydrocarbon group formed by removing a hydrogen atom from a cycloalkane molecule, preferably having 3 to 30 carbon atoms, preferably 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornane, etc., but are not limited thereto. The above-mentioned cycloalkyl group is preferably cyclopentane, cyclohexane, 1-adamantyl, 2-adamantyl, norbornane.

[0028] The aryl group described in the present invention refers to a general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon nucleus of an aromatic compound molecule, which can be a monocyclic aryl group, a polycyclic aryl group or a condensed aryl group, preferably 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 group refers to an aryl group having only one aromatic ring in the molecule, such as phenyl, etc., but not limited thereto; the polycyclic aryl group refers to an aryl group containing two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, etc., but not limited thereto; the condensed aryl group refers to an aryl group containing two or more aromatic rings in the molecule and fused to each other by sharing two adjacent carbon atoms, such as naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylene, fluoranthenyl, spirobifluorenyl, etc., but not limited thereto. The above-mentioned aryl group 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.

[0029] The heteroaryl group described in the present invention refers to a general term for a group in which one or more aromatic carbon atoms in the aromatic group are replaced by heteroatoms, wherein the heteroatoms include but are not limited to oxygen, sulfur, nitrogen or phosphorus atoms, preferably having 5 to 30 ring atoms (5 to 30 members), further preferably having 5 to 20 ring atoms (5 to 20 members), more preferably 6 to 24 ring atoms (6 to 24 members), particularly preferably 6 to 13 ring atoms (6 to 13 members), and most preferably 6 to 12 ring atoms (6 to 12 members); 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 attachment site of the heteroaryl group may be located on a ring-forming carbon atom or a ring-forming nitrogen atom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a condensed-ring heteroaryl group. The monocyclic heteroaryl groups include pyridyl, pyrimidinyl, triazine, furanyl, thienyl, pyrrolyl, imidazolyl, etc., but are not limited thereto; the polycyclic heteroaryl groups include bipyridyl, bipyrimidinyl, phenylpyridyl, etc., but are not limited thereto; the condensed ring heteroaryl groups include quinolyl, isoquinolyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, etc., but are not limited thereto. The above-mentioned heteroaryl group is preferably pyridyl, pyrimidinyl, thienyl, furyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, benzodibenzothienyl, benzodibenzofuranyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, spirofluorenyloxanthenyl, spirofluorenylthioanthenyl and the like.

[0030] The group formed by the fusion of aromatic ring and aliphatic ring of the present invention refers to the general term for a monovalent group after the aromatic ring and aliphatic ring (cycloalkyl, cycloalkenyl, cycloalkynyl) are fused together and one hydrogen atom is removed. 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 aliphatic ring preferably has 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, and also preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. Examples include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, etc., but are not limited thereto.

[0031] The arylene group described in the present invention 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.

[0032] The divalent group formed by the fusion of an aromatic ring and an aliphatic ring described in the present invention refers to a group formed by the fusion of an aromatic ring and an aliphatic 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 aliphatic ring provided above can be applied to it, except that the divalent group formed by the fusion of an aromatic ring and an aliphatic ring is a divalent group.

[0033] The heteroarylene group described in the present invention 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.

[0034] The "substitution" described in the present invention refers to the replacement of a hydrogen atom in certain functional groups by another atom or functional group (i.e., a substituent), and the position of the substitution is not limited as long as the position is the position where the hydrogen atom is replaced, and when two or more are substituted, the two or more substituents may be the same or different from each other.

[0035] The substituents in the "substituted or unsubstituted" of the present invention may be independently selected from 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 heterocyclyl, 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 arylamine 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; more preferably 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, bornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, peryl, pyrenyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexanyl, 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, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, o-phenanthroline, furanyl, thienyl, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, phenothiazinyl, phenoxazinyl, one or more thereof; when there are multiple substituents, the multiple substituents are the same or different from each other.

[0036] In the specification, "*-" means a part connected to another substituent. "*-" can be connected to any optional position of the connected group / fragment. For example express And so on.

[0037] In this specification, when the position of a substituent on a ring is not fixed, it means that it can be connected to any of the corresponding optional positions of the ring. For example, Can be expressed And so on.

[0038] In this specification, when a substituent or a bond at a connection site runs through two or more rings, it indicates that it can be connected to any of the two or more rings, specifically, it can be connected to any of the corresponding optional sites of the ring. For example, Can be expressed or Can be expressed And so on.

[0039] The term "connected to form a ring" used in the present invention refers to two groups connected to each other by a chemical bond and optionally aromatized. For example:

[0040]

[0041] In the present invention, the ring formed by connection can be an aromatic ring system, an aliphatic ring system or a ring system formed by the fusion of the two, and can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring or a condensed ring, such as benzene, naphthalene, indene, fluorene, cyclopentene, cyclopentane, cyclopentane acene, cyclohexene, cyclohexane, cyclohexane acene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but not limited thereto.

[0042] The present invention provides an organic electroluminescent device, comprising an anode, a cathode, an organic layer and a covering layer, wherein the covering layer is located outside at least one of the anode and the cathode, and is characterized in that the covering layer comprises a compound represented by Formula 1:

[0043]

[0044] The X is independently selected from N or CR a ;

[0045] The R a Any one independently selected from 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 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 R a They may be connected to form a substituted or unsubstituted ring;

[0046] The L is independently selected from any one of a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensing 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 group;

[0047] A and B are independently selected from Formula 2 or Formula 3, and at least one of A and B is selected from Formula 3;

[0048]

[0049] Ar is selected from any one of a substituted or unsubstituted C6-C30 aromatic group, a group formed by condensing 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 group;

[0050] The L a , L b Any one independently selected from 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 aliphatic ring, or a substituted or unsubstituted 5-30 membered heteroarylene group;

[0051] The Y is selected from O, S or NR p ;

[0052] The R p Any one independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0053] The X 1 Independently selected from N or CR c ;

[0054] The R b , R c Any one independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 5-30 membered heteroaryl; or two adjacent R c They may be connected to form a substituted or unsubstituted ring;

[0055] The b is selected from 0, 1 or 2.

[0056] Preferably, the substituent in the "substituted or unsubstituted" is selected from 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 C The invention can be selected from the group consisting of a 3-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 arylamine group or a substituted or unsubstituted C1-C30 silane group. When multiple substituents are present, the multiple substituents may be the same or different from each other.

[0057] Preferably, Ar is selected from any one of the following groups:

[0058]

[0059] The R d Any one 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 R d They can be connected to form substituted or unsubstituted rings;

[0060] The E is independently selected from N or CH;

[0061] The Y 1 Selected from O, S, NR e or C(R f ) 2 ;

[0062] The R e Any one 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 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted 5-20 membered heteroaryl; or R e Can be directly with L a Bonding;

[0063] The R fAny one 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 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted 5-20 membered heteroaryl; or two R f Any one of them can be directly compared with L a Bonding;

[0064] The C is selected from a substituted or unsubstituted C3-C12 aliphatic ring;

[0065] The Y 2 Selected from single bond, O, S, NR g or C(R h ) 2 ;

[0066] The R g Any one 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 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted 5-20 membered heteroaryl;

[0067] The R h Any one 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 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted 5-20 membered heteroaryl;

[0068] The Y 3 Selected from O, S or NR i ;

[0069] The R i Any one 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 condensation of a substituted or unsubstituted C6-C20 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted 5-20-membered heteroaryl;

[0070] The d 1 Independently selected from 0, 1, 2, 3, 4 or 5; said d 2 Independently selected from 0, 1, 2, 3 or 4; said d 3Independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; said d 4 are independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said d 5 Independently selected from 0, 1, 2 or 3; said d 6 are independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0071] Preferably, Ar is selected from any one of the following groups:

[0072]

[0073]

[0074] The R d independently selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, or substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bornyl, norbornyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, peryl, pyrenyl, any one of benzophenone, benzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, phenothiazinyl and phenoxazinyl;

[0075] The Y 1 Selected from O, S, NR e or C(R f ) 2 ;

[0076] The R e independently selected from hydrogen, deuterium, trifluoromethyl, or 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, bornyl, norbornyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, peryl, pyrenyl, R is any one of benzophenone, benzocyclobutane, benzocyclopentane, benzocyclohexane, fluorenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, acridinyl, o-phenanthroline, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, phenothiazinyl, and phenoxazinyl; or R e Can be directly with L a Bonding;

[0077] The R f independently selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, or substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bornyl, norbornyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, peryl, pyrenyl, any one of benzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, phenothiazinyl and phenoxazinyl; or two R f Any one of them can be directly compared with L a Bonding;

[0078] The Y 2 Selected from single bond, O, S, NR g or C(R h ) 2 ;

[0079] The R g independently selected from hydrogen, deuterium, trifluoromethyl, or 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, bornyl, norbornyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, peryl, pyrenyl, any one of benzophenone, benzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, phenothiazinyl and phenoxazinyl;

[0080] The R h independently selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, or substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bornyl, norbornyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, peryl, pyrenyl, any one of benzophenone, benzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, phenothiazinyl and phenoxazinyl;

[0081] The Y 3 Selected from O, S or NR i ;

[0082] The R i is selected from hydrogen, deuterium, trifluoromethyl, or 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, bornyl, norbornyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, peryl, pyrenyl, any one of benzophenone, benzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, phenothiazinyl and phenoxazinyl;

[0083] The d 0 independently selected from 0 or 1; said d 1 Independently selected from 0, 1, 2, 3, 4 or 5; said d 2 Independently selected from 0, 1, 2, 3 or 4; said d 3 Independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; said d 4 are independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said d 5 Independently selected from 0, 1, 2 or 3; said d 6 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said d 7 Independently selected from 0, 1 or 2; said d 8Independently selected from 0, 1, 2, 3, 4, 5 or 6; said d 9 are independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; 10 are independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said d 11 independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; said d 12 independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14;

[0084] The R d ~R i The “substituted or unsubstituted” 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, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantyl, bornane, norbornyl, phenyl, and deuterated phenyl. When multiple substituents are present, the multiple substituents may be the same or different from each other.

[0085] Preferably, in Formula 3 One selected from the following groups:

[0086]

[0087] The Y is selected from O, S or NR p ;

[0088] The R b , R c independently selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, or substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bornyl, norbornyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, peryl, pyrenyl, any one of benzophenone, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, phenothiazinyl and phenoxazinyl; or two adjacent R cThey can be connected to form any one of a substituted or unsubstituted benzene 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, and a substituted or unsubstituted pyrazine ring;

[0089] The R p independently selected from hydrogen, deuterium, trifluoromethyl, or 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, bornyl, norbornyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, peryl, pyrenyl, any one of benzophenone, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, phenothiazinyl and phenoxazinyl;

[0090] The b is independently selected from 0, 1 or 2;

[0091] The c 1 Independently selected from 0, 1, 2, 3 or 4; said c 2 Independently selected from 0, 1, 2 or 3; said c 3 Independently selected from 0, 1 or 2; said c 4 Independently selected from 0 or 1;

[0092] The R b , R c , R p The “substituted or unsubstituted” 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, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantyl, bornane, norbornyl, phenyl, and deuterated phenyl. When multiple substituents are present, the multiple substituents may be the same or different from each other.

[0093] More preferably, in Formula 3 Any one selected from the following groups:

[0094]

[0095]

[0096]

[0097] The Y is selected from O, S or NR p ;

[0098] The R p independently selected from hydrogen, deuterium, trifluoromethyl, or 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, bornyl, norbornyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, peryl, pyrenyl, any one of benzoxazolyl, benzoimidazolyl, benzothiazolyl, carbazolyl, phenothiazinyl and phenoxazinyl.

[0099] The R p The “substituted or unsubstituted” 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, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantyl, bornane, norbornyl, phenyl, and deuterated phenyl. When multiple substituents are present, the multiple substituents may be the same or different from each other.

[0100] Preferably, L is selected from any one of the following groups:

[0101]

[0102] The R j Any one 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 or substituted or unsubstituted 5-20 membered heteroaryl; or two adjacent R j They may be connected to form a substituted or unsubstituted ring;

[0103] The Y 4 Selected from O, S, NR k or C(R l ) 2 ;

[0104] The R k Any one 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 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted 5-20 membered heteroaryl;

[0105] The R l Any one 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 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted 5-20 membered heteroaryl; or two R l They may be connected to form a substituted or unsubstituted ring;

[0106] The Z is independently selected from N or CH;

[0107] The 1 Independently selected from 0, 1, 2, 3 or 4; said e 2 Independently selected from 0, 1, 2 or 3; said e 3 Independently selected from 0, 1 or 2; said e 4 Independently selected from 0, 1, 2, 3, 4, 5 or 6; said e 5 are independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0108] More preferably, L is selected from any one of the following groups:

[0109]

[0110]

[0111]

[0112]

[0113] The R j independently selected from hydrogen, deuterium, halogen, trifluoromethyl, cyano, or 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, bornyl, norbornyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, peryl, pyrenyl, any one of benzophenone, benzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl and carbazolyl;

[0114] The R k independently selected from hydrogen, deuterium, trifluoromethyl, or 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, bornyl, norbornyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, peryl, pyrenyl, any one of benzophenone, benzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl and carbazolyl;

[0115] The R l independently selected from hydrogen, deuterium, halogen, trifluoromethyl, cyano, or 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, bornyl, norbornyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, peryl, pyrenyl, any one of benzophenone, benzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl and carbazolyl;

[0116] The 0 independently selected from 0 or 1; said e 1 Independently selected from 0, 1, 2, 3 or 4; said e 2 Independently selected from 0, 1, 2 or 3; said e 3 Independently selected from 0, 1 or 2; said e 4 Independently selected from 0, 1, 2, 3, 4, 5 or 6; said e 5 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said e 6Independently selected from 0, 1, 2, 3, 4 or 5; said e 7 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said e 8 independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14;

[0117] The R j ~R l The “substituted or unsubstituted” 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, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantyl, bornane, norbornyl, phenyl, and deuterated phenyl. When multiple substituents are present, the multiple substituents may be the same or different from each other.

[0118] Preferably, the L a , L b Independently selected from a single bond or any one of the following groups:

[0119]

[0120] The R m Any one 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 or substituted or unsubstituted 5-20 membered heteroaryl; or two adjacent R m They may be connected to form a substituted or unsubstituted ring;

[0121] The Y 5 Selected from O, S, NR n or C(R o ) 2 ;

[0122] The R n Any one 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 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted 5-20 membered heteroaryl;

[0123] The R oAny one 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 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted 5-20 membered heteroaryl; or two R o They may be connected to form a substituted or unsubstituted ring;

[0124] The V is independently selected from N or CH;

[0125] The f 1 Independently selected from 0, 1, 2, 3 or 4; said f 2 Independently selected from 0, 1, 2 or 3; said f 3 independently selected from 0, 1 or 2; said f 4 Independently selected from 0, 1, 2, 3, 4, 5 or 6; said f 5 are independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0126] More preferably, the L a , L b Independently selected from a single bond or any one of the following groups:

[0127]

[0128]

[0129] The R m independently selected from hydrogen, deuterium, halogen, trifluoromethyl, cyano, or 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, bornyl, norbornyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, peryl, pyrenyl, any one of benzophenone, benzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl and carbazolyl;

[0130] The R nindependently selected from hydrogen, deuterium, trifluoromethyl, or 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, bornyl, norbornyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, peryl, pyrenyl, any one of benzophenone, benzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl and carbazolyl;

[0131] The R o independently selected from hydrogen, deuterium, halogen, trifluoromethyl, cyano, or 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, bornyl, norbornyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, peryl, pyrenyl, any one of benzophenone, benzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl and carbazolyl;

[0132] The f 0 independently selected from 0 or 1; said f 1 Independently selected from 0, 1, 2, 3 or 4; said e 2 Independently selected from 0, 1, 2 or 3; said e 3 Independently selected from 0, 1 or 2; said e 4 Independently selected from 0, 1, 2, 3, 4, 5 or 6; said e 5 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said e 6 Independently selected from 0, 1, 2, 3, 4 or 5; said e 7 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said e 8 independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14;

[0133] The R m ~R oThe “substituted or unsubstituted” 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, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantyl, bornane, norbornyl, phenyl, and deuterated phenyl. When multiple substituents are present, the multiple substituents may be the same or different from each other.

[0134] Preferably, the covering layer comprises any one of the following structures:

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146] Only some specific structural forms of the compounds of Formula 1 are listed above, but the present invention is not limited to these chemical structures listed. All structures based on the structure shown in Formula 1 and substituents as defined above should be included.

[0147] The organic electroluminescent device of the present invention comprises an anode, a cathode, an organic layer and a covering layer.

[0148] As the organic layer of the present invention, it is located between the anode and the cathode. The organic layer includes a hole transport region, a light-emitting layer and an electron transport region, the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting auxiliary layer and other functional layers, the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer and other functional layers, and the organic layer can be increased or decreased accordingly according to actual needs.

[0149] The organic layer of the present invention may have the following structures: 1) a single-layer structure, which includes a single layer containing a single material; or a single layer containing multiple materials; 2) a multi-layer structure, which includes multiple layers containing multiple materials. Specifically, the hole transport layer may include a first hole transport layer and a second hole transport layer, and the electron transport layer may include a first electron transport layer and a second electron transport layer; specifically, the material used for each organic layer may be selected from inorganic materials, organic materials, or inorganic-organic materials formed by mixing the two, but is not limited thereto.

[0150] As the covering layer of the present invention, it is located outside at least one of the anode and the cathode. It can be a single-layer structure, a double-layer structure or a multi-layer structure; for example, the covering layer can include a first covering layer and a second covering layer. The material used for the covering layer can be selected from inorganic materials, organic materials or inorganic-organic materials formed by mixing the two, but is not limited thereto.

[0151] Preferably, the covering layer is located on the outer side of the cathode.

[0152] Preferably, the covering layer comprises the compound represented by Formula 1 described in the present invention.

[0153] Preferably, the organic electroluminescent device provided by the present invention has the following structure, but is not limited thereto:

[0154] (1) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode / covering layer

[0155] (2) Anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode / covering layer

[0156] (3) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode / covering layer

[0157] (4) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode / covering layer

[0158] (5) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode / covering layer

[0159] (6) Anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode / covering layer

[0160] As the anode material of the present invention, a material with a high work function is preferred. 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 (SnO 2 ), 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 may 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 may have a single-layer structure or a multi-layer structure including two or more layers, for example, the anode may 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.

[0161] As the hole injection layer material of the present invention, a material having good hole acceptance ability is preferred, and can be selected from any one or more of the following structures: metal porphyrin, oligothiophene, arylamine derivatives, perylene derivatives, hexanitrile hexaazatriphenylene compounds, quinacridone compounds, anthraquinone compounds, and polyaniline-based and polythiophene-based conductive polymers, but not limited thereto.

[0162] As the hole transport layer material of the present invention, a material with high hole mobility is preferred, and can be selected from any one or more of the following structures: carbazole derivatives, triarylamine derivatives, biphenyl diamine derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, hexanitrile hexaazatriphenylene compounds, quinacridone compounds, anthraquinone compounds, polyaniline, polythiophene, polyvinylcarbazole, etc., but not limited thereto.

[0163] The light-emitting layer material of the present invention may contain only a guest material, or may be in the form of a guest material dispersed in a host material, and may use two host materials to form a dual host material. The host material of the light-emitting layer not only needs to have bipolar charge transfer properties, but also needs to have an appropriate energy level to effectively transfer the excitation energy to the guest light-emitting material. This type of material can include distyryl aryl derivatives, isocyanate derivatives, carbazole derivatives, triarylamine derivatives, anthracene derivatives and pyrene derivatives. The guest material can be selected from any one or more 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 is not limited thereto.

[0164] As the electron injection layer material of the present invention, a material with a low work function is preferred. It can be selected from any one or more of the following structures: alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, and other substances with high electron injection properties. Examples include Li, Ca, Sr, LiF, CsF, CaF 2 、BaO、Li 2 CO 3 、CaCO 3 , Li 2 C 2 O 4 , Cs 2 C 2 O 4 , CsAlF 4 , LiOx, Yb, Tb, etc., but not limited to these.

[0165] As the electron transport layer material of the present invention, a material with high electron mobility is preferred, and can be selected from any one or more of the following structures: metal chelates, oxazoline derivatives, thiazole derivatives, diazole derivatives, azabenzene derivatives, diazaanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, quinoline derivatives, phenanthroline derivatives, benzimidazole derivatives, etc., but not limited thereto.

[0166] As the hole blocking layer of the present invention, a material with a lower energy level, a wider band gap and excellent hole blocking ability is preferred, and can be selected from any one or more of the following structures: phenanthroline derivatives, rare earth derivatives, oxazole derivatives, triazole derivatives, triazine derivatives, etc., but not limited thereto.

[0167] As the cathode material of the present invention, a material with a low work function is preferred. 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 for forming 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 for forming 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, including compounds thereof or mixtures thereof (e.g., a mixture of Ag and Mg), but not limited thereto.

[0168] As the covering layer material of the present invention, a material with high light extraction efficiency is preferred. In addition to the compound of formula 1 of the present invention, any one or more of the following structures can also be selected: for example, metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, aromatic amine compounds, etc., but not limited thereto. Preferably, the covering layer material uses the compound of formula 1 of the present invention.

[0169] There is no particular restriction on the method for preparing each thin film layer in the organic electroluminescent device of the present invention. It can be prepared by any method including vacuum evaporation, inkjet printing, sputtering, plasma, ion plating, spin coating, dipping, screen printing, etc., but is not limited thereto; there is no particular restriction on the thickness of each layer, as long as good device performance is obtained.

[0170] The organic electroluminescent device provided by the present invention can be applied to fields such as lighting and display, and can be specifically listed as smartphone display screens, tablet computer display screens, smart wearable device display screens, large-size displays such as televisions, and VR, etc.

[0171] The present invention is explained in more detail by the following examples, and the technical scheme and technical effects of the present invention are further described, but it is not intended to limit the present invention. On the basis of this description, a person of ordinary skill in the art will be able to implement the present invention and prepare other compounds and devices according to the present invention within the entire disclosed range without paying creative work.

[0172] The present invention also provides a method for preparing a compound of formula 1, but the preparation method of the present invention is not limited thereto, and the following is only an example of a synthetic route. The following synthetic routes all adopt the reaction types commonly used in organic synthesis, and the reaction conditions (for example, the selection of types, dosages, and order and method of addition of reaction solvents, catalysts, ligands, bases, etc.) are not particularly limited, and conventional methods and operations can be used.

[0173] The synthetic route of the compound of formula 1:

[0174]

[0175] The Xa, Xb, and Xc are independently selected from any one of Cl, Br, and I.

[0176] Description of raw materials, reagents and characterization equipment:

[0177] The present invention has no particular limitation on the sources of the raw materials used in the following examples, and the raw materials can be obtained by using commercially available raw materials or by using preparation methods well known to those skilled in the art.

[0178] The mass spectrum of the compound of the present invention was obtained using a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters, UK.

[0179] The elemental analysis of the compounds of the present invention was performed using a Vario EL cube organic element analyzer produced by Elementar of Germany.

[0180] [Synthesis Example 1] Synthesis of Compound 13

[0181]

[0182] Preparation of intermediate g-13:

[0183] Under nitrogen protection, e-13 (17.09 g, 70.00 mmol), f-13 (12.04 g, 70.00 mmol), tetrakistriphenylphosphine palladium (0.81 g, 0.70 mmol), potassium carbonate (19.35 g, 140 mmol) and 300 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to the reaction bottle in sequence, the mixture was stirred, and the above system was heated to reflux for reaction for 3 hours; after the reaction was completed, it was cooled to room temperature, the filter cake was filtered, and the filter cake was rinsed with ethanol, and finally the filter cake was recrystallized with toluene / methanol = 5:1 to obtain g-13 (12.45 g, yield 85%); HPLC purity ≥99.75%. Mass spectrum m / z: 209.0830 (theoretical value: 209.0841).

[0184] Preparation of intermediate j-13:

[0185] Under nitrogen protection, e-13 (17.09 g, 70.00 mmol), i-13 (25.13 g, 70.00 mmol), tetrakistriphenylphosphine palladium (0.81 g, 0.70 mmol), potassium carbonate (19.35 g, 140 mmol) and 300 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to the reaction bottle in sequence, the mixture was stirred, and the above system was heated to reflux for 4 hours; after the reaction was completed, it was cooled to room temperature, the filter cake was filtered, and the filter cake was rinsed with ethanol, and finally the filter cake was recrystallized with toluene / methanol = 5:1 to obtain j-13 (20.53 g, yield 84%); HPLC purity ≥99.78%. Mass spectrum m / z: 244.1283 (theoretical value: 244.1271).

[0186] Preparation of intermediate d-13:

[0187] Under nitrogen protection, j-13 (17.46 g, 50.00 mmol), g-13 (10.46 g, 50.00 mmol), palladium acetate (0.17 g, 0.60 mmol), sodium tert-butoxide (9.61 g, 100.00 mmol), tri-tert-butylphosphine (0.61 g, 3.00 mmol) and toluene (150 mL) were added to the reaction bottle in sequence, 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, 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 / ethanol = 4:1 to obtain d-13 (18.62 g, yield 78%), and the solid purity was ≥99.86% by HPLC. Mass spectrum m / z: 477.1718 (theoretical value: 477.1729).

[0188] Preparation of intermediate A-13:

[0189] Under nitrogen protection, a-13 (22.75 g, 70.00 mmol), b-13 (29.27 g, 140.00 mmol), 1,1-bis(diphenylphosphine)diferronipalladium dichloride (1.02 g, 1.40 mmol), potassium carbonate (38.70 g, 280.00 mmol) and 600 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to the reaction bottle, the mixture was stirred, and the above system was heated to reflux 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, and recrystallized with toluene / ethanol = 5:1 to obtain A-13 (17.30 g, yield 75%), and the solid purity was ≥99.77% by HPLC. Mass spectrum m / z: 329.1998 (theoretical value: 329.1989).

[0190] Preparation of intermediate B-13:

[0191] Under nitrogen protection, A-13 (16.47 g, 50.00 mmol), c-13 (9.57 g, 50.00 mmol), palladium acetate (0.17 g, 0.75 mmol), sodium tert-butyl alcohol (9.61 g, 100.00 mmol), tri-tert-butylphosphine (0.61 g, 3.00 mmol) and toluene (150 mL) were added to the reaction bottle in sequence, 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, extracted with dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized with toluene / ethanol = 10:1 to obtain B-13 (15.84 g, yield 72%), and the solid purity was ≥99.82% by HPLC. Mass spectrum m / z: 439.1901 (theoretical value: 439.1912).

[0192] Preparation of compound 13:

[0193] Under nitrogen protection, B-13 (13.20 g, 30.00 mmol), d-13 (14.33 g, 30.00 mmol), tridibenzylideneacetone dipalladium (0.27 g, 0.30 mmol), sodium tert-butoxide (5.77 g, 60.00 mmol), tri-tert-butylphosphine (0.37 g, 1.80 mmol) and toluene (100 mL) were added to the reaction bottle in sequence, the mixture was stirred, and the above system was heated to reflux 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 with toluene to obtain compound 13 (17.71 g, yield 67%). The solid purity detected by HPLC was ≥99.92%. Mass spectrum m / z: 880.3884 (theoretical value: 880.3874). Theoretical element content (%) C 64 H 32 D 10 N 2 O 2 :C, 87.24;H, 5.95;N, 3.18. Measured element content (%): C, 87.28;H, 5.90;N, 3.21.

[0194] [Synthesis Example 2] Synthesis of Compound 18

[0195]

[0196] According to the preparation method of Synthesis Example 1, j-13, g-13, b-13, c-13, d-13 were replaced by equimolar j-18, g-18, b-18, c-18, d-18, respectively, to obtain compound 18 (17.60 g). The solid purity was ≥ 99.93% by HPLC. Mass spectrum m / z: 850.3545 (theoretical value: 850.3559). Theoretical element content (%) C 62 H 46 N 2 O 2 :C, 87.50; H, 5.45; N, 3.29. Measured element content (%): C, 87.52; H, 5.43; N, 3.33.

[0197] [Synthesis Example 3] Synthesis of Compound 47

[0198]

[0199] According to the preparation method of Synthesis Example 1, j-13, A-13, c-13, d-13 were replaced by equimolar j-47, A-47, i-13, d-47, respectively, to obtain compound 47 (15.31 g). The solid purity was ≥ 99.97% by HPLC. Mass spectrum m / z: 718.2633 (theoretical value: 718.2620). Theoretical element content (%) C 52 H 34 N 2 O 2 :C, 86.88;H, 4.77;N, 3.90. Measured element content (%): C, 86.91;H, 4.75;N, 3.86.

[0200] [Synthesis Example 4] Synthesis of Compound 49

[0201]

[0202] According to the preparation method of Synthesis Example 1, i-13, g-13, A-13, c-13, d-13 were replaced by equimolar i-49, g-49, A-47, c-49, d-49, respectively, to obtain compound 49 (14.34 g). The solid purity was ≥ 99.98% by HPLC. Mass spectrum m / z: 682.2911 (theoretical value: 682.2922). Theoretical element content (%) C 50 H 30 D 4 N 2 O: C, 87.95; H, 5.61; N, 4.10. Measured element content (%): C, 87.91; H, 5.59; N, 4.13.

[0203] [Synthesis Example 5] Synthesis of Compound 60

[0204]

[0205] According to the preparation method of Synthesis Example 1, j-13, g-13, A-13, c-13, and d-13 were replaced by equimolar j-60, g-60, A-47, c-60, and d-60, respectively, to obtain compound 60 (14.28 g). The solid purity was ≥ 99.98% by HPLC. Mass spectrum m / z: 670.2249 (theoretical value: 670.2232). Theoretical element content (%) C 45 H 29 F 3 N 2 O: C, 80.58; H, 4.36; N, 4.18. Measured element content (%): C, 80.63; H, 4.35; N, 4.16.

[0206] [Synthesis Example 6] Synthesis of Compound 75

[0207]

[0208] According to the preparation method of Synthesis Example 1, e-13, i-13, g-13, A-13, c-13, d-13 were replaced by equimolar amounts of h-75, i-75, g-75, A-75, c-75, d-75, respectively, to obtain compound 75 (15.11 g). The solid purity was ≥ 99.97% by HPLC. Mass spectrum m / z: 729.2876 (theoretical value: 729.2890). Theoretical element content (%) C 54 H 35 DN 2 O: C, 88.86; H, 5.11; N, 3.84. Measured element content (%): C, 88.91; H, 5.08; N, 3.80.

[0209] [Synthesis Example 7] Synthesis of Compound 80

[0210]

[0211] According to the preparation method of Synthesis Example 1, e-13, i-13, g-13, A-13, c-13, d-13 were replaced by equimolar amounts of h-80, i-80, g-80, A-47, c-80, d-80, respectively, to obtain compound 80 (13.45 g). The solid purity was ≥ 99.98% by HPLC. Mass spectrum m / z: 631.2636 (theoretical value: 631.2624). Theoretical element content (%) C 45 H 33 N 3 O: C, 85.55; H, 5.27; N, 6.65. Measured element content (%): C, 85.59; H, 5.23; N, 6.63.

[0212] [Synthesis Example 8] Synthesis of Compound 83

[0213]

[0214] According to the preparation method of Synthesis Example 1, j-13, g-13, A-13, c-13, and d-13 were replaced by equimolar j-83, g-18, A-83, c-83, and d-83, respectively, to obtain compound 83 (17.12 g). The solid purity was ≥99.94% by HPLC. Mass spectrum m / z: 826.3542 (theoretical value: 826.3559). Theoretical element content (%) C 60 H 46 N 2 O 2:C, 87.14;H, 5.61;N, 3.39. Measured element content (%): C, 87.11;H, 5.58;N, 3.43.

[0215] [Synthesis Example 9] Synthesis of Compound 95

[0216]

[0217] According to the preparation method of Synthesis Example 1, j-13, g-13, A-13, c-13, and d-13 were replaced by equimolar j-95, g-18, A-95, c-95, and d-95, respectively, to obtain compound 95 (16.23 g). The solid purity was ≥ 99.97% by HPLC. Mass spectrum m / z: 772.3078 (theoretical value: 772.3090). Theoretical element content (%) C 56 H 46 N 2 O 2 :C, 87.02;H, 5.22;N, 3.62. Measured element content (%): C, 87.07;H, 5.25;N, 3.60.

[0218] [Synthesis Example 10] Synthesis of Compound 99

[0219]

[0220] According to the preparation method of Synthesis Example 1, e-13, i-13, g-13, A-13, c-13, and d-13 were replaced by equimolar amounts of h-99, i-99, g-99, A-47, c-99, and d-99, respectively, to obtain compound 99 (16.45 g). The solid purity was ≥ 99.95% by HPLC. Mass spectrum m / z: 818.2958 (theoretical value: 818.2933). Theoretical element content (%) C 60 H 38 N 2 O 2 :C, 88.00;H, 4.68;N, 3.42. Measured element content (%): C, 88.05;H, 4.65;N, 3.44.

[0221] [Synthesis Example 11] Synthesis of Compound 111

[0222]

[0223] According to the preparation method of Synthesis Example 1, j-13, g-13, A-13, c-13, and d-13 were replaced by equimolar j-111, g-111, A-47, c-111, and d-111, respectively, to obtain compound 111 (15.38 g). The solid purity was ≥ 99.97% by HPLC. Mass spectrum m / z: 753.2765 (theoretical value: 753.2780). Theoretical element content (%) C 55 H 35 N 3 O: C, 87.62; H, 4.68; N, 5.57. Measured element content (%): C, 87.65; H, 4.63; N, 5.54.

[0224] [Synthesis Example 12] Synthesis of Compound 112

[0225]

[0226] According to the preparation method of Synthesis Example 1, j-13, g-13, A-13, c-13, and d-13 were replaced by equimolar j-112, g-112, A-47, c-112, and d-112, respectively, to obtain compound 112 (14.57 g). The solid purity was ≥ 99.98% by HPLC. Mass spectrum m / z: 703.2638 (theoretical value: 703.2624). Theoretical element content (%) C 51 H 33 N 3 O: C, 87.03; H, 4.73; N, 5.97. Measured element content (%): C, 87.01; H, 4.76; N, 5.94.

[0227] [Synthesis Example 13] Synthesis of Compound 131

[0228]

[0229] According to the preparation method of Synthesis Example 1, j-13, g-13, A-13, c-13, d-13 were replaced by equimolar j-131, g-18, A-131, i-13, d-131, respectively, to obtain compound 131 (14.79 g). The solid purity was ≥ 99.96% by HPLC. Mass spectrum m / z: 735.3238 (theoretical value: 735.3250). Theoretical element content (%) C 53 H 41 N 3 O: C, 86.50; H, 5.62; N, 5.71. Measured element content (%): C, 86.53; H, 5.60; N, 5.73.

[0230] [Synthesis Example 14] Synthesis of Compound 132

[0231]

[0232] According to the preparation method of Synthesis Example 1, i-13, g-13, A-13, c-13, and d-13 were replaced by equimolar c-80, g-132, A-132, c-132, and d-132, respectively, to obtain compound 132 (15.62 g). The solid purity was ≥ 99.95% by HPLC. Mass spectrum m / z: 788.3380 (theoretical value: 788.3391). Theoretical element content (%) C 56 H 28 D 8 N 4 O: C, 85.25; H, 5.62; N, 7.10. Measured element content (%): C, 85.28; H, 5.60; N, 7.13.

[0233] [Synthesis Example 15] Synthesis of Compound 137

[0234]

[0235] According to the preparation method of Synthesis Example 1, i-13, g-13, A-13, c-13, and d-13 were replaced by equimolar i-137, g-137, A-137, c-60, and d-137, respectively, to obtain compound 137 (14.52 g). The solid purity was ≥ 99.97% by HPLC. Mass spectrum m / z: 711.2982 (theoretical value: 711.2998). Theoretical element content (%) C 49 H 37 N 5 O: C, 82.68; H, 5.24; N, 9.84. Measured element content (%): C, 82.65; H, 5.26; N, 9.81.

[0236] [Synthesis Example 16] Synthesis of Compound 150

[0237]

[0238] According to the preparation method of Synthesis Example 1, j-13, g-13, A-13, c-13, and d-13 were replaced by equal moles of j-150, g-150, A-150, c-150, and d-150, respectively, to obtain compound 150 (16.48 g). The solid purity was ≥99.96% by HPLC. Mass spectrum m / z: 795.3265 (theoretical value: 795.3250). Theoretical element content (%) C 58 H 41 N3 O: C, 87.52; H, 5.19; N, 5.28. Measured element content (%): C, 87.56; H, 5.17; N, 5.24.

[0239] [Synthesis Example 17] Synthesis of Compound 163

[0240]

[0241] According to the preparation method of Synthesis Example 1, j-13, A-13, c-13, and d-13 were replaced by equimolar j-163, A-47, c-163, and d-163, respectively, to obtain compound 163 (13.52 g). The solid purity was ≥ 99.98% by HPLC. Mass spectrum m / z: 662.2109 (theoretical value: 662.2118). Theoretical element content (%) C 44 H 27 FN 4 O 2 :C, 79.74;H, 4.11;N, 8.45. Measured element content (%): C, 79.71;H, 4.07;N, 8.50.

[0242] [Synthesis Example 18] Synthesis of Compound 175

[0243]

[0244] According to the preparation method of Synthesis Example 1, j-13, g-13, A-13, c-13, and d-13 were replaced by equimolar j-175, g-175, A-175, c-175, and d-175, respectively, to obtain compound 175 (14.89 g). The solid purity was ≥ 99.96% by HPLC. Mass spectrum m / z: 740.3278 (theoretical value: 740.3264). Theoretical element content (%) C 50 H 40 N 6 O: C, 81.06; H, 5.44; N, 11.34. Measured element content (%): C, 81.02; H, 5.39; N, 11.38.

[0245] [Synthesis Example 19] Synthesis of Compound 178

[0246]

[0247] According to the preparation method of Synthesis Example 1, j-13, g-13, A-13, c-13, and d-13 were replaced with equal moles of j-178, g-178, A-150, c-178, and d-178, respectively, to obtain compound 178 (14.57 g). The solid purity was ≥ 99.98% by HPLC. Mass spectrum m / z: 693.2515 (theoretical value: 693.2529). Theoretical element content (%) C 48 H 31 N 5 O: C, 83.10; H, 4.50; N, 10.09. Measured element content (%): C, 83.12; H, 4.54; N, 10.05.

[0248] [Synthesis Example 20] Synthesis of Compound 187

[0249]

[0250] According to the preparation method of Synthesis Example 1, j-13, g-13, b-13, c-13, and d-13 were replaced by equimolar j-187, g-187, b-187, i-49, and d-187, respectively, to obtain compound 187 (17.77 g). The solid purity was ≥ 99.91% by HPLC. Mass spectrum m / z: 883.3237 (theoretical value: 883.3219). Theoretical element content (%) C 62 H 29 D 9 N 2 O 2 S: C, 84.23; H, 5.36; N, 3.17. Measured element content (%): C, 84.19; H, 5.38; N, 3.18.

[0251] [Synthesis Example 21] Synthesis of Compound 193

[0252]

[0253] According to the preparation method of Synthesis Example 1, j-13, g-13, A-13, and d-13 were replaced by equimolar j-193, g-193, A-47, and d-193, respectively, to obtain compound 193 (13.27 g). The solid purity was ≥ 99.99% by HPLC. Mass spectrum m / z: 622.1525 (theoretical value: 622.1537). Theoretical element content (%) C 42 H 26 N 2 S 2 :C, 81.00;H, 4.21;N, 4.50. Measured element content (%): C, 79.98;H, 4.23;N, 4.45.

[0254] [Synthesis Example 22] Synthesis of Compound 210

[0255]

[0256] According to the preparation method of Synthesis Example 1, e-13, f-13, j-13, g-13, a-13, b-13, c-13, d-13 were replaced by equimolar amounts of h-99, f-210, j-210, g-210, a-210, b-210, i-13, d-210, respectively, to obtain compound 210 (18.60 g). The solid purity was ≥ 99.91% by HPLC. Mass spectrum m / z: 938.3459 (theoretical value: 938.3443). Theoretical element content (%) C 67 H 46 N 4 S: C, 85.68; H, 4.94; N, 5.97. Measured element content (%): C, 85.65; H, 4.98; N, 5.94.

[0257] [Synthesis Example 23] Synthesis of Compound 223

[0258]

[0259] According to the preparation method of Synthesis Example 1, j-13, g-13, A-13, c-13, and d-13 were replaced by equimolar j-187, g-223, A-223, c-49, and d-223, respectively, to obtain compound 223 (13.00 g). The solid purity was ≥ 99.98% by HPLC. Mass spectrum m / z: 627.2571 (theoretical value: 627.2584). Theoretical element content (%) C 43 H 21 D 8 N 3 S: C, 82.26; H, 5.94; N, 6.69. Measured element content (%): C, 82.23; H, 5.98; N, 6.65.

[0260] [Synthesis Example 24] Synthesis of Compound 229

[0261]

[0262] According to the preparation method of Synthesis Example 1, e-13, i-13, g-13, A-13, c-13, and d-13 were replaced with equal moles of h-229, i-229, g-229, A-229, i-13, and d-229, respectively, to obtain compound 229 (17.69 g). The solid purity was ≥ 99.92% by HPLC. Mass spectrum m / z: 893.2661 (theoretical value: 893.2647). Theoretical element content (%) C 60 H 39 N 5 S 2 :C, 80.60;H, 4.40;N, 7.83. Measured element content (%): C, 80.56;H, 4.37;N, 7.87.

[0263] [Synthesis Example 25] Synthesis of Compound 242

[0264]

[0265] According to the preparation method of Synthesis Example 1, j-13, g-13, A-13, c-13, and d-13 were replaced by equimolar j-242, g-193, A-47, c-242, and d-242, respectively, to obtain compound 242 (14.16 g). The solid purity was ≥ 99.98% by HPLC. Mass spectrum m / z: 683.2050 (theoretical value: 683.2031). Theoretical element content (%) C 47 H 29 N 3 OS: C, 82.55; H, 4.27; N, 6.14. Measured element content (%): C, 82.57; H, 4.25; N, 6.18.

[0266] [Synthesis Example 26] Synthesis of Compound 260

[0267]

[0268] According to the preparation method of Synthesis Example 1, e-13, i-13, g-13, A-13, c-13, and d-13 were replaced with equal moles of h-260, i-260, g-260, A-260, c-260, and d-260, respectively, to obtain compound 260 (14.66 g). The solid purity was ≥ 99.97% by HPLC. Mass spectrum m / z: 697.2476 (theoretical value: 697.2490). Theoretical element content (%) C 49 H 27 D 4 N 3S: C, 84.33; H, 5.05; N, 6.02. Measured element content (%): C, 84.30; H, 5.01; N, 6.06.

[0269] [Synthesis Example 27] Synthesis of Compound 267

[0270]

[0271] According to the preparation method of Synthesis Example 1, j-13, g-13, A-13, c-13, and d-13 were replaced by equimolar j-267, g-267, A-47, c-267, and d-267, respectively, to obtain compound 267 (15.57 g). The solid purity was ≥ 99.94% by HPLC. Mass spectrum m / z: 762.3059 (theoretical value: 762.3069). Theoretical element content (%) C 55 H 42 N 2 S: C, 86.58; H, 5.55; N, 3.67. Measured element content (%): C, 86.54; H, 5.58; N, 3.65.

[0272] [Synthesis Example 28] Synthesis of Compound 272

[0273]

[0274] According to the preparation method of Synthesis Example 1, j-13, g-13, A-13, c-13, and d-13 were replaced with equal moles of j-272, g-272, A-47, c-272, and d-272, respectively, to obtain compound 272 (15.05 g). The solid purity was ≥99.95% by HPLC. Mass spectrum m / z: 748.2901 (theoretical value: 748.2912). Theoretical element content (%) C 54 H 40 N 2 S: C, 86.60; H, 5.38; N, 3.74. Measured element content (%): C, 86.58; H, 5.41; N, 3.76.

[0275] [Synthesis Example 29] Synthesis of Compound 292

[0276]

[0277] According to the preparation method of Synthesis Example 1, j-13, g-13, A-13, c-13, and d-13 were replaced with equal moles of j-292, g-292, A-47, c-292, and d-292, respectively, to obtain compound 292 (13.64 g). The solid purity was ≥ 99.95% by HPLC. Mass spectrum m / z: 658.2458 (theoretical value: 658.2443). Theoretical element content (%) C 47 H 34 N 2 S: C, 85.68; H, 5.20; N, 4.25. Measured element content (%): C, 85.64; H, 5.25; N, 4.22.

[0278] [Synthesis Example 30] Synthesis of Compound 303

[0279]

[0280] According to the preparation method of Synthesis Example 1, e-13, i-13, g-13, A-13, c-13, d-13 were replaced by equimolar amounts of h-303, i-303, g-49, A-303, c-75, d-303, respectively, to obtain compound 303 (14.50 g). The solid purity was ≥ 99.96% by HPLC. Mass spectrum m / z: 710.2516 (theoretical value: 710.2504). Theoretical element content (%) C 49 H 34 N 4 S: C, 82.79; H, 4.82; N, 7.88. Measured element content (%): C, 82.83; H, 4.85; N, 7.84.

[0281] [Synthesis Example 31] Synthesis of Compound 367

[0282]

[0283] According to the preparation method of Synthesis Example 1, j-13, g-13, B-13, and d-13 were replaced by equimolar j-367, g-367, B-47, and d-367, respectively, to obtain compound 367 (14.55 g). The solid purity was ≥ 99.98% by HPLC. Mass spectrum m / z: 692.2558 (theoretical value: 692.2576). Theoretical element content (%) C 49 H 32 N 4 O: C, 84.95; H, 4.66; N, 8.09. Measured element content (%): C, 84.91; H, 4.62; N, 8.14.

[0284] [Device Example 1]

[0285] First, the glass substrate with ITO / Ag / ITO vapor-deposited was cleaned twice in distilled water, ultrasonically washed for 30 minutes, and then repeatedly cleaned twice with distilled water, ultrasonically washed for 10 minutes. After the distilled water cleaning, ultrasonically washed with isopropyl alcohol, acetone, and methanol solvents in sequence, and then dried on a hot plate heated to 120°C. The dried substrate was transferred to a plasma cleaning machine and transferred to a vapor deposition machine after washing for 5 minutes.

[0286] Then, HI-1 was evaporated on the cleaned ITO / Ag / ITO substrate as a hole injection layer with a deposition thickness of 10 nm, HT-1 was evaporated on the hole injection layer as a hole transport layer with a deposition thickness of 90 nm, and then a mixture of GH-1, GH-2 and GD-1 (mass ratio GH-1:GH-2:GD-1=46:46:8) was vacuum evaporated on the hole transport layer to form a light-emitting layer with a deposition thickness of 35 nm, ET-1 and Liq (mass ratio of 1:1) were evaporated on the light-emitting layer as an electron transport layer with a deposition thickness of 40 nm, and LiF was evaporated on the electron transport layer as an electron injection layer with a deposition thickness of 1 nm, and then Mg:Ag (mass ratio of 1:9) was evaporated on the electron injection layer as a cathode with a deposition thickness of 15 nm, and then the compound 13 of the present invention was vacuum evaporated on the cathode as a covering layer with a deposition thickness of 70 nm, thereby preparing an organic electroluminescent device 1.

[0287]

[0288] [Device Examples 2 to 31]

[0289] Organic electroluminescent devices 2 to 31 are prepared by using Compound 18, Compound 47, Compound 49, Compound 60, Compound 75, Compound 80, Compound 83, Compound 95, Compound 99, Compound 111, Compound 112, Compound 131, Compound 132, Compound 137, Compound 150, Compound 163, Compound 175, Compound 178, Compound 187, Compound 193, Compound 210, Compound 223, Compound 229, Compound 242, Compound 260, Compound 267, Compound 272, Compound 292, Compound 303 and Compound 367 of the present invention instead of Compound 13 in Device Example 1 as a covering layer. Except for this, the other preparation steps are the same as those of Device Example 1, and the organic electroluminescent devices 2 to 31 are prepared.

[0290] [Comparative Device Examples 1 to 3]

[0291] Comparative compounds 1, 2 and 3 were used to replace compound 13 in device example 1 as the covering layer. Other preparation steps were the same as those in device example 1 to prepare comparative devices 1 to 3.

[0292] The test software, computer, K2400 digital source meter produced by Keithley Company of the United States and PR788 spectrum scanning luminance meter of PhotoResearch Company of the United States are combined into a joint IVL test system to test the driving voltage and luminous efficiency of the organic electroluminescent device. The life test adopts the M6000 OLED life test system of McScience Company. The test environment is the atmospheric environment and the temperature is room temperature. The luminous characteristics test results of the organic electroluminescent devices obtained by devices 1 to 31 in the device embodiment of the present invention and comparative examples 1 to 3 are shown in Table 1 below.

[0293] [Table 1] Luminescence characteristics test of organic electroluminescent devices

[0294]

[0295]

[0296]

[0297] It can be seen from the results in Table 1 that, compared with the comparative devices 1 to 3, the organic electroluminescent devices 1 to 31 of the present invention can effectively couple out the light trapped in the device, thereby improving the light extraction efficiency of the device, thereby improving the luminous efficiency of the organic electroluminescent device and extending the service life of the organic electroluminescent device.

[0298] It should be noted that the present invention is particularly described using individual implementation schemes. For those skilled in the art, several improvements and modifications may be made to the present invention without departing from the principles of the present invention, and these improvements and modifications also fall within the protection of the present invention.

Claims

1. An organic electroluminescent device, comprising an anode, a cathode, an organic layer and a covering layer, wherein the covering layer is located outside at least one of the anode and the cathode, characterized in that: The covering layer comprises a compound represented by Formula 1: At most two of the X are selected from N, and the rest are independently selected from CR a ; The R a any one independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl; or two adjacent R a can be connected to form a substituted or unsubstituted benzene ring; the R a The "substituted or unsubstituted" substituent is selected from deuterium; The L is selected from any one of the following groups: The R j Independently selected from hydrogen, deuterium, halogen, trifluoromethyl, cyano, or substituted or unsubstituted groups: any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl; The R j1 Independently selected from hydrogen, deuterium, or substituted or unsubstituted groups: any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl; The R k Independently selected from the following substituted or unsubstituted groups: any one of phenyl, biphenyl, and naphthyl; The R l Independently selected from the following groups, substituted or unsubstituted: any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, and naphthyl; The e1 is independently selected from 0, 1, 2, 3 or 4; the e2 is independently selected from 0, 1, 2 or 3; the e3 is independently selected from 0, 1 or 2; the e4 is independently selected from 0, 1, 2, 3, 4, 5 or 6; the e5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; The R j , R j1 , R k , R l The "substituted or unsubstituted" substituent is selected from deuterium; A and B are independently selected from Formula 2 or Formula 3, and at least one of A and B is selected from Formula 3; The Ar is selected from any one of the following groups: The R d independently selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, or substituted or unsubstituted groups: any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, adamantyl, phenyl, biphenyl, and naphthyl; The R d1 Independently selected from hydrogen, deuterium, or substituted or unsubstituted groups: any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl; The Y1 is selected from O, S, NR e or C(R f )2; The R e Independently selected from the following substituted or unsubstituted groups: any one of phenyl, biphenyl, and naphthyl; The R f Independently selected from the following substituted or unsubstituted groups: any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, and naphthyl; Said Y3 is selected from O or S; One of the E's is selected from N, and the others are selected from CH; The d1 is independently selected from 0, 1, 2, 3, 4 or 5; the d2 is independently selected from 0, 1, 2, 3 or 4; the d3 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; the d4 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the d5 is independently selected from 0, 1, 2 or 3; the d6 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the d7 is independently selected from 0, 1 or 2; the d8 is independently selected from 0, 1, 2, 3, 4, 5 or 6; 10 are independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said d 11 independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; said d 12 independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; The R d , R d1 , R e , R f , R i The "substituted or unsubstituted" substituent is selected from deuterium; The L a , L b Independently selected from a single bond or any one of the following groups: The R m Independently selected from hydrogen, deuterium, or substituted or unsubstituted groups: any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl; The f1 is independently selected from 0, 1, 2, 3 or 4; the f2 is independently selected from 0, 1, 2 or 3; the f3 is independently selected from 0, 1 or 2; The R m The "substituted or unsubstituted" substituent is selected from deuterium; In the formula 3 One selected from the following groups: The Y is selected from O, S or NR p ; The R b , R c , R c1 independently selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, or substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, phenyl, biphenyl, naphthyl; or two adjacent R c1 They can be connected to form substituted or unsubstituted benzene rings; The R p Independently selected from the following substituted or unsubstituted groups: any one of phenyl, biphenyl, and naphthyl; The b is independently selected from 0, 1 or 2; Said c1 is independently selected from 0, 1, 2, 3 or 4; said c2 is independently selected from 0, 1, 2 or 3; said c3 is independently selected from 0, 1 or 2; The R b , R c , R c1 , R p The "substituted or unsubstituted" substituents are selected from deuterium.

2. An organic electroluminescent device according to claim 1, characterized in that: The Ar is selected from any one of the following groups: The R d Independently selected from any one of hydrogen and deuterium; The R d1 Independently selected from any one of hydrogen and deuterium; The R f Independently selected from the following substituted or unsubstituted groups: any one of methyl, isopropyl, tert-butyl, phenyl, biphenyl and naphthyl.

3. The organic electroluminescent device according to claim 1, characterized in that: In the formula 3 One selected from the following groups: The R b , R c , R c1 Independently selected from any one of hydrogen and deuterium.

4. The organic electroluminescent device according to claim 1, characterized in that: In the formula 3 Any one selected from the following groups:

5. The organic electroluminescent device according to claim 1, characterized in that: The L is selected from any one of the following groups:

6. The organic electroluminescent device according to claim 1, characterized in that: The L a , L b Independently selected from a single bond or any one of the following groups:

7. An organic electroluminescent device, comprising an anode, a cathode, an organic layer and a covering layer, wherein the covering layer is located outside at least one of the anode and the cathode, characterized in that: The covering layer comprises any one of the following structures:

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