Heterocyclic compound and organic electroluminescent device thereof

Abstract

The application provides a heterocyclic compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic electroluminescent materials.The heterocyclic compound has a high refractive index, can effectively reduce total reflection loss and waveguide loss in the organic electroluminescent device, couple out the light trapped in the device, improve the light extraction efficiency of the device, and in addition, the compound has a high glass transition temperature and good thermal stability, when the compound is applied to the organic electroluminescent device to be evaporated into a thin film, the thin film has high stability and is not easy to crystallize, can effectively isolate water and oxygen in the air, and avoid the problem of sharp roll-off of the efficiency of the device, when the compound is applied to the covering layer of the organic electroluminescent device, the luminous efficiency of the device can be effectively improved and the service life of the device can be prolonged.

Description

TECHNICAL FIELD

[0001] The application belongs to the technical field of organic electroluminescent materials, and particularly relates to a heterocyclic compound and an organic electroluminescent device thereof. BACKGROUND

[0002] With the rapid development of science and technology, the importance of display technology is increasingly highlighted, and people's requirements for display performance are constantly improving. The shortcomings of liquid crystal display technology are gradually revealed. In order to meet the growing needs of consumers, organic light-emitting diodes (OLED) as a new display technology gradually occupy the market. Compared with liquid crystal display technology, OLED has excellent performance such as light weight, small thickness, wide viewing angle, low energy consumption, high efficiency, wide adaptability, good color purity, fast response speed, and is widely used in lighting and display and many other fields.

[0003] The light-emitting principle of OLED is that holes and electrons are injected from the anode and cathode into the organic layer under the action of an external electric field, then enter the light-emitting layer through the hole transport region and the electron transport region, and the two are recombined in the light-emitting layer to generate excitons and release energy. Excitons migrate under the action of an electric field, transfer energy to light-emitting substances in the light-emitting layer, and the electrons in the light-emitting substance molecules transition from the ground state to the excited state, and then from the excited state to the ground state. In this process, energy is released in the form of light. 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 and the like. These organic functional layers play an important role in improving the driving voltage, light-emitting efficiency, color purity, service life and other properties of OLED devices. In order to improve the light-emitting efficiency of OLED devices, a cover layer with a higher refractive index is provided outside a semi-transparent electrode with a lower refractive index.

[0004] The application of the cover layer can reduce the total reflection loss and waveguide loss in the OLED device, couple out the light trapped in the device, enhance the light extraction efficiency, and thus improve the light-emitting efficiency of the device and prolong the service life of the device. However, the light extraction efficiency of conventional OLED devices is low, so how to improve the light extraction efficiency of OLED has become the focus of current research. Due to the large gap between the external quantum efficiency and the internal quantum efficiency of OLED, total reflection occurs at the interface between the ITO film and the glass substrate and the interface between the glass substrate and the air, resulting in that the light emitted to the external space of the OLED device accounts for about 20% of the total amount of organic material film EL, and the remaining 80% of the light is mainly limited in the form of waveguide in the organic material film, ITO film and glass substrate, which greatly limits the development of OLED.

[0005] However, at present, the research on the covering layer material is less at home and abroad, therefore, in order to better solve the problems of low luminous efficiency and service life of the organic light-emitting device, a new covering layer material with excellent performance needs to be designed. SUMMARY

[0006] To solve the above technical problems, the present application provides a heterocyclic compound and an organic electroluminescent device thereof, which can effectively improve the luminous efficiency of the organic electroluminescent device and prolong the service life of the organic electroluminescent device when applied to the covering layer of the organic electroluminescent device. The technical scheme of the present application is as follows:

[0007] The present application provides a heterocyclic compound, which is represented by the structure shown in formula 1:

[0008]

[0009] The Ar1 is selected from formula 2:

[0010]

[0011] The R1, R2 is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aryl ring and substituted or unsubstituted C3-C8 aliphatic ring fused to form a group, substituted or unsubstituted C3-C30 heteroaryl, and substituted or unsubstituted silyl group;

[0012] The a is selected from 0, 1, 2 or 3; when there are two or more R1, the two or more R1 are the same or different from each other;

[0013] The c is selected from 0, 1, 2, 3, 4, 5 or 6; when there are two or more R2, the two or more R2 are the same or different from each other;

[0014] The Ar2 is selected from formula 3:

[0015]

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

[0017] The ring A, ring B is independently selected from any one of substituted or unsubstituted benzene ring, substituted or unsubstituted naphthalene ring, substituted or unsubstituted anthracene ring, substituted or unsubstituted phenanthrene ring, and substituted or unsubstituted triphenylene ring; and ring A and ring B cannot be substituted or unsubstituted benzene ring at the same time;

[0018] The Ar3 is selected from any one of formula 2 or the following structure:

[0019]

[0020] said x1, x2 are independently selected from N or CH; x1, x2 at the bond are selected from C; and at least two of said x2 are selected from N;

[0021] said ring C is selected from substituted or unsubstituted C3-C10 cycloalkyl;

[0022] said Y1 is selected from O, S, C(R5)2 or NR6; said Y2 is selected from O, S, C(R7)2 or NR8;

[0023] said R3, R4, R5, R7 are independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aryl ring fused with substituted or unsubstituted C3-C8 alicyclo ring, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted silyl; or adjacent two R4, adjacent two R5 can be connected to form a substituted or unsubstituted ring; any one of said two R5 can be directly bonded to L3;

[0024] said R6, R8 are independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aryl ring fused with substituted or unsubstituted C3-C8 alicyclo ring, substituted or unsubstituted C3-C30 heteroaryl; said R6, R8 can be directly bonded to L3;

[0025] said b1 is selected from 0, 1, 2, 3, 4 or 5; said b2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said b4 is selected from 0, 1, 2, 3 or 4; said b5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said b6 is selected from 0, 1 or 2; said b7 is selected from 0, 1, 2 or 3; when there are two or more R3, R4, two or more R3, R4 are the same or different from each other;

[0026] said L1, L2 are independently selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 aryl ring fused with substituted or unsubstituted C3-C7 alicyclo bivalent group, substituted or unsubstituted C3-C30 heteroarylene, or a combination thereof;

[0027] said L3 is selected from single bond or any one of the following structures:

[0028]

[0029] said e is selected from N or CH; e at the bond is selected from C; and at most two of said e is selected from N;

[0030] said ring D is selected from substituted or unsubstituted C3-C10 cycloalkyl;

[0031] said Y3 is selected from O, S, C(R b )2 or NR c ;

[0032] said R a , R b is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, a group fused from substituted or unsubstituted C6-C30 aryl ring and substituted or unsubstituted C3-C8 alicyclic ring, substituted or unsubstituted C3-C30 heteroaryl, and substituted or unsubstituted silyl; or said two R b may be linked to form a substituted or unsubstituted ring; or any one of said two R b may be directly bonded to Ar3;

[0033] said R c is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, a group fused from substituted or unsubstituted C6-C30 aryl ring and substituted or unsubstituted C3-C8 alicyclic ring, and substituted or unsubstituted C3-C30 heteroaryl;

[0034] said n1 is selected from 0, 1, 2, 3 or 4; said n2 is selected from 0, 1, 2 or 3; said n3 is selected from 0, 1 or 2; when there are two or more R a , the two or more R a are the same or different from each other.

[0035] The present application also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer between the anode and the cathode or outside one or more of the anode and the cathode, wherein the organic layer comprises any one or more of the heterocyclic compounds.

[0036] Advantages:

[0037] The present application provides a kind of heterocyclic compound and its organic electroluminescent device, the heterocyclic compound described in the present application has higher refractive index, can effectively reduce the total reflection loss and waveguide loss in OLED device, the light trapped in the device is coupled out, improve the light extraction efficiency of device, in addition, the compound described in the present application also has higher glass transition temperature and good thermal stability, when it is applied to organic electroluminescent device and evaporated into thin film, thin film stability is high and not easy to crystallize, also can effectively isolate water and oxygen in air, avoid the problem of sharp roll-off of device efficiency, so, when it is applied to organic electroluminescent device as cover layer, it can effectively improve the luminous efficiency of device and prolong the service life of device. DETAILED DESCRIPTION

[0038] The technical solutions of the specific embodiments of the present application will be described below clearly and completely, obviously, the described embodiments are only a part of the embodiments of the present application, not all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative labor belong to the protection scope of the present application.

[0039] In the compound of the present application, any atom not specified as a particular isotope is included as any stable isotope of that atom, and includes atoms in both their natural isotopic abundance and non-natural abundance.

[0040] The halogen described in the present application refers to fluorine, chlorine, bromine and iodine.

[0041] The alkyl described in the present application refers to a monovalent group after removing one hydrogen atom from an alkane molecule, which can be linear alkyl, branched alkyl, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The linear alkyl includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl and the like, but is not limited thereto; the branched alkyl 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 and the like, but is not limited thereto. The above-mentioned alkyl is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl.

[0042] The alicyclic group of the present application refers to a monovalent group formed by removing one hydrogen atom from an alicyclic hydrocarbon molecule, which can be a cycloalkyl group, a cycloalkenyl group, etc., preferably has 3 to 20 carbon atoms, more preferably 3 to 15 carbon atoms, further preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms, and examples can include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantyl group, a norbornyl group, a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, etc., but is not limited thereto.

[0043] The aryl group of the present application refers to a monovalent group formed by removing one hydrogen atom from the aromatic nucleus carbon of an aromatic compound molecule, which can be a monocyclic aryl group, a polycyclic aryl group, or a fused ring aryl group, preferably has 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, for example, a phenyl group, etc., but is not limited thereto; the polycyclic aryl group refers to an aryl group having two or more independent aromatic rings in the molecule, for example, a biphenyl group, a terphenyl group, etc., but is not limited thereto; and the fused ring aryl group refers to an aryl group having two or more aromatic rings in the molecule and being fused by sharing two adjacent carbon atoms, for example, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a fluorenyl group, a benzofluorenyl group, a triphenylenyl group, a fluoranthenyl group, a spirobifluorenyl group, etc., but is not limited thereto. The aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a spirobifluorenyl group, a spiro-cyclopentyl-fluorenyl group, a spiro-cyclohexyl-fluorenyl group, a spiro-adamantyl-fluorenyl group, a spiro-cyclopentenyl-fluorenyl group, or a spiro-cyclohexenyl-fluorenyl group.

[0044] The heteroaryl group according to the present application refers to a monovalent group formed by replacing one or more aromatic ring carbon atoms in an aryl group with a heteroatom, including but not limited to oxygen, sulfur, nitrogen or phosphorus atom, preferably having 3 to 30 carbon atoms, preferably having 3 to 22 carbon atoms, more preferably having 3 to 16 carbon atoms, most preferably 3 to 8 carbon atoms, which can be monocyclic heteroaryl group, polycyclic heteroaryl group or fused ring heteroaryl group. The monocyclic heteroaryl group includes pyridyl, pyrimidyl, triazinyl, furanyl, thienyl, pyrrolyl, imidazolyl, etc., but is not limited thereto; the polycyclic heteroaryl group includes bipyridyl, bipyrimidyl, phenylpyridyl, etc., but is not limited thereto; the fused ring heteroaryl group includes quinolyl, isoquinolyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzo-dibenzofuranyl, dibenzothienyl, benzo-dibenzothienyl, carbazolyl, benzocarbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxazinyl, etc., but is not limited thereto. The above heteroaryl group is preferably pyridyl, pyrimidyl, thienyl, furanyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, benzo-dibenzothienyl, benzo-dibenzofuranyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenoxazinyl, spirofluorenoxanthene, spirofluorenothioxanthene, etc.

[0045] The group according to the present application in which an aromatic ring is fused with an aliphatic ring refers to a monovalent group formed by removing one hydrogen atom from an aromatic ring and an aliphatic ring (cycloalkyl, cycloalkenyl, cycloalkynyl) fused together. The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, most preferably 6 to 12 carbon atoms, and the aliphatic ring preferably has 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, further preferably 3 to 12 carbon atoms, most preferably 3 to 7 carbon atoms, and examples include benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexanyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropanyl, naphthocyclobutanyl, naphthocyclopentanyl, naphthocyclohexanyl, naphthocyclopentenyl, naphthocyclohexenyl, etc., but is not limited thereto.

[0046] The "substituted or unsubstituted silyl group" according to the present application refers to a -Si(R z )3 group, in which each R zthe same or different groups selected from the group consisting of hydrogen, deuterium, tritium, a cyano group, a halogen, a nitro group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkenyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted C3-C30 alicyclic ring and C6-C60 aromatic ring fused ring group, and a substituted or unsubstituted C3-C30 alicyclic ring and C2-C60 heteroaromatic ring fused ring group. Preferably, each R z the same or different groups selected from the group consisting of hydrogen, deuterium, tritium, a cyano group, a halogen, a nitro group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group. The number of carbon atoms of the alkyl group is preferably 1 to 20, preferably 1 to 15, more preferably 1 to 10, and most preferably 1 to 8. The number of carbon atoms of the cycloalkyl group is preferably 3 to 20, preferably 3 to 15, more preferably 3 to 10, and most preferably 3 to 7. The number of carbon atoms of the aryl group is preferably 6 to 20, preferably 6 to 13, more preferably 6 to 12, and most preferably 6 to 10. Preferably, each R z the same or different groups selected from the group consisting of hydrogen, deuterium, tritium, a cyano group, a halogen, a nitro group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group. The number of carbon atoms of the alkyl group is preferably 1 to 20, preferably 1 to 15, more preferably 1 to 10, and most preferably 1 to 8. The number of carbon atoms of the cycloalkyl group is preferably 3 to 20, preferably 3 to 15, more preferably 3 to 10, and most preferably 3 to 7. The number of carbon atoms of the aryl group is preferably 6 to 20, preferably 6 to 13, more preferably 6 to 12, and most preferably 6 to 10. Preferably, each R

[0047] The arylene group according to the present application refers to a divalent group in which two hydrogen atoms are removed from the aromatic ring carbon of an aromatic hydrocarbon molecule. The description provided above for the aryl group can be applied, except that the arylene group is a divalent group.

[0048] The bivalent group in which an aromatic ring and an aliphatic ring are fused together according to the present application means a bivalent group in which an aromatic ring and an aliphatic ring (cycloalkyl, cycloalkenyl, cycloalkynyl) are fused together and two hydrogen atoms are removed. The description provided above for the group in which an aromatic ring and an aliphatic ring are fused together can be applied, except that the group in which an aromatic ring and an aliphatic ring are fused together is a bivalent group.

[0049] The heteroarylene group according to the present application means a bivalent group in which two hydrogen atoms are removed from the ring carbon of the core of an aromatic heterocycle composed of carbon and heteroatoms. The description provided above for the heteroaryl group can be applied, except that the heteroarylene group is a bivalent group.

[0050] In the present specification, the "*" is a bond.

[0051] In the present specification, when a substituent or a bonding site is indicated to be "attached to" two or more rings, it means that it can be attached to any one of the two or more rings, specifically, to any one of the corresponding optional sites of the rings. For example, may mean may mean and the like.

[0052] In the present specification, when the position of a substituent or a bonding site on a ring is not fixed, it means that it can be attached to any one of the optional sites of the ring. For example, may mean may mean may mean and the like.

[0053] In the present specification, means a moiety bonded to another substituent.

[0054] In the present specification, when the position of a bonded substituent on a ring is not fixed, it means that it can be attached to any two adjacent carbon atoms of the corresponding optional sites of the ring, for example, bonded to may mean and the like.

[0055] The "connection to form a ring" according to the present application means that each group is connected to each other by a chemical bond, and optionally forms a double bond / triple bond, and can constitute an aromatic group, as exemplified below:

[0056]

[0057] In the present application, the ring formed by the connection can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of both, 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 benzene, cyclohexene, cyclohexane, cyclohexane benzene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, etc., but are not limited thereto.

[0058] The "unsubstituted" in the "substituted or unsubstituted" of the present application means that the hydrogen atoms on the group are not replaced by any substituent. The "substituted" in the "substituted or unsubstituted" of the present application means that at least one hydrogen atom on the group is replaced by a substituent, and the position of substitution is not limited as long as it is a position where a hydrogen atom is replaced. When a plurality of hydrogens is replaced by a plurality of substituents, the plurality of substituents can be the same or different.

[0059] The substituent represented by "substitution" in "substitution or non-substitution" according to the present application includes the following groups: deuterium, tritium, cyano, nitro, hydroxyl, halogen, substituted or non-substituted C1 to C15 alkyl, substituted or non-substituted C2 to C15 alkenyl, substituted or non-substituted C3 to C15 alicyclic group, substituted or non-substituted silyl group, substituted or non-substituted C6 to C30 aryl group, substituted or non-substituted C3 to C30 heteroaryl group, substituted or non-substituted condensed ring group of C3 to C15 alicyclic group and C6 to C30 aryl group, substituted or non-substituted condensed ring group of C3 to C15 alicyclic group and C3 to C30 heteroaryl group, substituted or non-substituted C1 to C12 alkoxy group, substituted or non-substituted C1 to C12 alkylthio group, substituted or non-substituted C6 to C30 aryloxy group, substituted or non-substituted C6 to C30 arylamino group, and the like, but is not limited thereto. The substituent is preferably the following group: deuterium, tritium, cyano, fluorine, chlorine, bromine, iodine, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropane group, cyclobutane group, cyclopentane group, cyclohexane group, cyclobutene group, cyclopentene group, cyclohexene group, cyclopentadiene group, cyclohexadiene group, adamantane group, norbornane group, trifluoromethyl group, benzcyclopropane group, benzcyclobutane group, benzcyclopentane group, benzcyclohexane group, benzcycloheptane group, benzcyclobutene group, benzcyclopentene group, benzcyclohexene group, phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthryl group, triphenylene group, 9,9-dimethylfluorene group, 9,9-diphenylfluorene group, 9,9'-spirobifluorene group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, quinoxalinyl group, phenanthrolinyl group, benzoxazolyl group, benzothiazolyl group, benzimidazolyl group, benzofuranyl group, dibenzofuranyl group, benzothiophenyl group, dibenzothiophenyl group, indolyl group, carbazolyl group, 9-phenylcarbazolyl group, trimethylsilyl group, triethylsilyl group, tri-t-butylsilyl group, triphenylsilyl group, and the like. In addition, each of the above substituents can be substituted or non-substituted, and two adjacent substituents can be linked to form a ring.

[0060] The present application provides a heterocyclic compound represented by the structure of formula 1:

[0061]

[0062] The Ar1 is selected from formula 2:

[0063]

[0064] R1, R2are independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C15 alicyclyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aryl ring fused with substituted or unsubstituted C3-C8 alicyclyl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted silyl group;

[0065] a is selected from 0, 1, 2 or 3; when two or more R1are present, the two or more R1are the same or different from each other;

[0066] c is selected from 0, 1, 2, 3, 4, 5 or 6; when two or more R2are present, the two or more R2are the same or different from each other;

[0067] Ar2is selected from formula 3:

[0068]

[0069] Y is selected from O or S;

[0070] ring A, ring B are independently selected from any one of substituted or unsubstituted benzene ring, substituted or unsubstituted naphthalene ring, substituted or unsubstituted anthracene ring, substituted or unsubstituted phenanthrene ring, substituted or unsubstituted triphenylene ring; and ring A and ring B cannot be substituted or unsubstituted benzene ring at the same time;

[0071] Ar3is selected from formula 2 or any one of the following structures:

[0072]

[0073] x1, x2are independently selected from N or CH; x1, x2at the bonding site are selected from C; and at least two of x2are selected from N;

[0074] ring C is selected from substituted or unsubstituted C3-C10 alicyclyl;

[0075] Y1is selected from O, S, C(R5)2or NR6; Y2is selected from O, S, C(R7)2or NR8;

[0076] R3, R4, R5, R7are independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C15 alicyclyl, substituted or unsubstituted C6-C30 aryl, a group fused from substituted or unsubstituted C6-C30 aryl ring and substituted or unsubstituted C3-C8 alicyclyl ring, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted silyl; or two adjacent R4, two adjacent R5may be connected to form a substituted or unsubstituted ring; any one of the two R5may be directly bonded to L3;

[0077] R6, R8are independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C15 alicyclyl, substituted or unsubstituted C6-C30 aryl, a group fused from substituted or unsubstituted C6-C30 aryl ring and substituted or unsubstituted C3-C8 alicyclyl ring, substituted or unsubstituted C3-C30 heteroaryl; R6, R8may be directly bonded to L3;

[0078] b1 is selected from 0, 1, 2, 3, 4 or 5; b2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; b4 is selected from 0, 1, 2, 3 or 4; b5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; b6 is selected from 0, 1 or 2; b7 is selected from 0, 1, 2 or 3; when there are two or more R3, R4, the two or more R3, R4are the same or different from each other;

[0079] L1, L2are independently selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, a divalent group fused from substituted or unsubstituted C6-C30 aryl ring and substituted or unsubstituted C3-C7 alicyclyl ring, substituted or unsubstituted C3-C30 heteroarylene, or a combination thereof;

[0080] L3is selected from single bond or any one of the following structures:

[0081]

[0082] e is selected from N or CH; e at the bonding site is selected from C; and at most two of e are selected from N;

[0083] ring D is selected from substituted or unsubstituted C3-C10 alicyclyl;

[0084] Y3is selected from O, S, C(R b )2or NR c ;

[0085] said R a , R b is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C15 alicyclyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aryl ring fused with substituted or unsubstituted C3-C8 alicyclyl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted silyl; or said two R b may be linked to form a substituted or unsubstituted ring; or any one of said two R b may be directly bonded to Ar3;

[0086] said R c is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C15 alicyclyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aryl ring fused with substituted or unsubstituted C3-C8 alicyclyl, substituted or unsubstituted C3-C30 heteroaryl;

[0087] said n1 is selected from 0, 1, 2, 3 or 4; said n2 is selected from 0, 1, 2 or 3; said n3 is selected from 0, 1 or 2; when there are two or more R a , two or more R a are the same or different from each other.

[0088] Preferably, said R2 is selected from hydrogen, deuterium, cyano, halogen, trifluoromethyl, or any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, hexyl, cyclopropanyl, cyclobutanyl, cyclopentanoyl, cyclohexanoyl, adamantoyl, norbornanoyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, benzocyclobutanoyl, benzocyclopentanoyl, benzocyclohexanoyl, fluorenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthrydinyl, indolyl, acridinyl, phenanthrolinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazoyl, trimethylsilyl, triethylsilyl, tri-t-butylsilyl, triphenylsilyl.

[0089] said substituent of "substituted or unsubstituted" in said R2 is selected from one or more of deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopentanoyl, cyclohexanoyl, adamantoyl, norbornanoyl, phenyl, biphenyl, naphthyl, when there are two or more substituents, two or more substituents are the same or different from each other.

[0090] Preferably, the ring A, ring B is independently selected from any one of the following structures:

[0091]

[0092] and ring A and ring B cannot be simultaneously

[0093] the R9is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C15 alicyclic group, a group fused from substituted or unsubstituted C6-C30 aromatic ring and substituted or unsubstituted C3-C8 alicyclic ring, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted silyl group;

[0094] the d1is selected from 0, 1, 2, 3 or 4; the d2is selected from 0, 1, 2, 3, 4, 5 or 6; the d3is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R9, the two or more R9are the same or different from each other.

[0095] Preferably, the formula 3 is selected from any one of the following structures:

[0096]

[0097]

[0098] the Y is selected from O or S;

[0099] the R9is selected from hydrogen, deuterium, cyano, halogen, trifluoromethyl, or any one of the following groups substituted or unsubstituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopentane group, cyclohexane group, adamantane group, camphane group, norbornane group, phenyl group, biphenyl group, naphthyl group, anthracene group, phenanthrene group, triphenylene group, benzocyclobutane group, benzocyclopentane group, benzocyclohexane group, fluorene group, pyridyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, indolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzoxazolyl group, benzothiazolyl group, benzimidazolyl group, carbazolyl group, trimethylsilyl group, triethylsilyl group, tri-t-butylsilyl group, triphenylsilyl group;

[0100] d1 is selected from 0, 1, 2, 3, or 4; d2 is selected from 0, 1, 2, 3, 4, 5, or 6; d3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; d4 is selected from 0, 1, 2, or 3; d5 is selected from 0, 1, 2, 3, 4, or 5; d6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; when two or more R9 are present, two or more R9 are the same or different from each other.

[0101] The substituents of "substituted or unsubstituted" in R9 are selected from one or more of deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, when two or more substituents are present, two or more substituents are the same or different from each other.

[0102] Preferably, Ar3 is selected from any one of formula 2 or the following structures:

[0103]

[0104] Y1 is selected from O, S, C(R5)2, or NR6; Y2 is selected from O, S, C(R7)2, or NR8;

[0105] R3, R4, R5, R7 are independently selected from hydrogen, deuterium, cyano, halogen, trifluoromethyl, or any one of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, fluorenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, trimethylsilyl, triethylsilyl, tri-t-butylsilyl, triphenylsilyl; or any one of the two R5 can be directly bonded to L3;

[0106] R6 and R8 are independently selected from any one of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, camphenyl, norbornelyl, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, fluorenyl, pyridyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, indolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzooxazolyl, benzothiazolyl, benzimidazolyl, carbazoleyl, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl; or R6 and R8 can be directly bonded to L3;

[0107] The R d Selected from hydrogen, deuterium, cyano, halogen, trifluoromethyl, or any one of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, camphene, norbornyl, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, benzocyclopentane, benzocyclohexane, fluorenyl, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl;

[0108] The b1 is selected from 0, 1, 2, 3, 4, or 5; the b2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the b4 is selected from 0, 1, 2, 3, or 4; the b5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the b6 is selected from 0, 1, or 2; the b7 is selected from 0, 1, 2, or 3; the b8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the b9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the b 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; The b 11 Selected from 0, 1, 2, 3, 4, 5 or 6; when there are two or more R3s and R4s, the two or more R3s and R4s are the same or different from each other.

[0109] R3~R8, R d The substituents in "substituted or unsubstituted" are selected from one or more of deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, camphenyl, norbornel, phenyl, biphenyl, and naphthyl. When two or more substituents are present, the two or more substituents are the same as or different from each other.

[0110] Further preferred, Ar3 is selected from any one of formula 2 or the following structures:

[0111]

[0112]

[0113]

[0114] R3, R4, R5, R7 are independently selected from hydrogen, deuterium, cyano, halogen, trifluoromethyl, or any one of the following groups substituted or unsubstituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, benzocyclopentyl, benzocyclohexyl, fluorenyl, pyridyl, pyrimidyl, pyridazyl, pyrazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, indolyl, carbazolyl, trimethylsilyl, triethylsilyl, tri-t-butylsilyl, triphenylsilyl;

[0115] R6, R8 are independently selected from any one of the following groups substituted or unsubstituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, benzocyclopentyl, benzocyclohexyl, fluorenyl, pyridyl, pyrimidyl, pyridazyl, pyrazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, indolyl, carbazolyl, trimethylsilyl, triethylsilyl, tri-t-butylsilyl, triphenylsilyl;

[0116] R d R1 is selected from hydrogen, deuterium, cyano, halogen, trifluoromethyl, or any one of the following groups substituted or unsubstituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, benzocyclopentyl, benzocyclohexyl, fluorenyl, trimethylsilyl, triethylsilyl, tri-t-butylsilyl, triphenylsilyl;

[0117] The b1 is selected from 0, 1, 2, 3, 4, or 5; the b2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the b4 is selected from 0, 1, 2, 3, or 4; the b5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the b6 is selected from 0, 1, or 2; the b7 is selected from 0, 1, 2, or 3; the b8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the b9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the b 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; The b 11 Selected from 0, 1, 2, 3, 4, 5 or 6; when there are two or more R3s and R4s, the two or more R3s and R4s are the same or different from each other.

[0118] R3~R8, R d The substituents in "substituted or unsubstituted" are selected from one or more of deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, camphenyl, norbornel, phenyl, biphenyl, and naphthyl. When two or more substituents are present, the two or more substituents are the same as or different from each other.

[0119] Preferably, L1 and L2 are independently selected from single bonds or any of the following structures:

[0120]

[0121] The z is selected from N or CH; the z at the bonding site is selected from C; and at most two of the z are selected from N.

[0122] The Y3 is selected from O, S, C(R) 11 )2 or NR 12 ;

[0123] The R 10 R 11 Independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl, a group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring with a substituted or unsubstituted C3-C8 alicyclic ring, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted silyl; or two adjacent R 10 Two adjacent R 11 They can be connected to form substituted or unsubstituted rings; or the two Rs can be connected to form substituted or unsubstituted rings. 11any one of R1and R2may be directly bonded to Ar1or Ar2;

[0124] said R 12 any one of R1and R2may be directly bonded to Ar1or Ar2; 12 any one of R1and R2may be directly bonded to Ar1or Ar2;

[0125] said e1is selected from 0, 1, 2, 3 or 4; said e2is selected from 0, 1, 2 or 3; said e3is selected from 0, 1 or 2; said e4is selected from 0, 1, 2, 3, 4, 5 or 6; said e5is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R 10 , R 10 are the same or different from each other.

[0126] more preferably, said L1, L2are independently selected from a single bond or any one of the following structures:

[0127]

[0128]

[0129]

[0130] said R 10 , R 11 are independently selected from hydrogen, deuterium, cyano, halogen, trifluoromethyl, or any one of the following groups substituted or unsubstituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, camphane, norbornane, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylene, benzocyclobutane, benzocyclopentane, benzocyclohexane, fluorene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, trimethylsilyl, triethylsilyl, tri-t-butylsilyl, triphenylsilyl; or two adjacent R 10 may be connected to form a substituted or unsubstituted ring;

[0131] said R 12selected from the group consisting of hydrogen, deuterium, cyano, halogen, trifluoromethyl, or any one or more of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexanyle, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, benzocyclopentanyle, benzocyclohexanyle, fluorenyl, trimethylsilyl, triethylsilyl, tri-t-butylsilyl, triphenylsilyl;

[0132] said R e selected from the group consisting of hydrogen, deuterium, cyano, halogen, trifluoromethyl, or any one or more of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropanyl, cyclobutanyl, cyclopentanyle, cyclohexanyle, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, benzocyclopentanyle, benzocyclohexanyle, fluorenyl, trimethylsilyl, triethylsilyl, tri-t-butylsilyl, triphenylsilyl;

[0133] said e1 is selected from 0, 1, 2, 3 or 4; said e2 is selected from 0, 1, 2 or 3; said e3 is selected from 0, 1 or 2; said e4 is selected from 0, 1, 2, 3, 4, 5 or 6; said e5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said e6 is selected from 0, 1, 2, 3, 4 or 5; said e7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said e8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; when there are two or more R 10 , two or more R 10 are the same as or different from each other.

[0134] said R 10 ~R 12 , R e , the substituents of "substituted or unsubstituted" are selected from deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopentanyle, cyclohexanyle, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, one or more of which are substituted or unsubstituted, and when there are two or more substituents, two or more substituents are the same as or different from each other.

[0135] Preferably, said L3 is selected from a single bond or any one of the following structures:

[0136]

[0137] said R a , R b is independently selected from hydrogen, deuterium, cyano, halogen, trifluoromethyl, or any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexanyl, fluorenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophene, carbazolyl, trimethylsilyl, triethylsilyl, tri-t-butylsilyl, triphenylsilyl;

[0138] said R c is selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexanyl, fluorenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophene, carbazolyl, trimethylsilyl, triethylsilyl, tri-t-butylsilyl, triphenylsilyl;

[0139] said R f is selected from hydrogen, deuterium, cyano, halogen, trifluoromethyl, or any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, benzocyclopentanyl, benzocyclohexanyl, fluorenyl, trimethylsilyl, triethylsilyl, tri-t-butylsilyl, triphenylsilyl;

[0140] said R a ~R c , R f The substituent of "substituted or unsubstituted" in the above-mentioned groups is selected from one or more of deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, when two or more substituents exist, the two or more substituents are the same or different from each other.

[0141] Preferably, the heterocyclic compound is selected from any one of the following structures:

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159] The above only lists some specific structural forms of the heterocyclic compounds shown in Formula 1, but the present application is not limited to the listed chemical structures, and any substitution group defined above based on Formula 1 should be included.

[0160] The present application also provides an organic electroluminescent device comprising an anode, a cathode, and an organic layer between the anode and the cathode or outside one or more of the anode and the cathode, wherein the organic layer comprises any one or more of the heterocyclic compounds of the present application.

[0161] Preferably, the organic layer is outside one or more of the anode and the cathode, and the organic layer comprises a cover layer, wherein the cover layer comprises any one or more of the heterocyclic compounds of the present application.

[0162] As the organic layer according to the present application, a hole transport region including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting auxiliary layer, and the like, a light emitting layer, an electron transport region including a hole blocking layer, an electron transport layer, an electron injection layer, and the like, and a cover layer can be included. The organic functional layer can be increased or decreased according to necessity.

[0163] As the organic layer according to the present application, a single layer structure including a single layer including a single material or a single layer including a plurality of materials, and a multi-layer structure including a plurality of layers including a plurality of materials can be included. Specifically, the hole transport layer can include a first hole transport layer and a second hole transport layer, and the electron transport layer can include a first electron transport layer and a second electron transport layer. Specifically, the material for each organic functional layer can be selected from an inorganic material, an organic material, or an inorganic-organic material formed by mixing the inorganic material and the organic material, but is not limited thereto.

[0164] As the anode material according to the present application, a material having a high work function is preferred. The anode can be a transparent electrode, a reflective electrode, or a semi-transparent electrode. When the anode is a transparent electrode, the material for forming the anode can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (Sn02), zinc oxide (ZnO), or any combination thereof. When the anode is a semi-transparent electrode or a reflective electrode, the material for forming 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.

[0165] As the hole injection layer material according to the present application, a material having a good hole accepting ability is preferred. Any one or more of the following structures can be selected: metalloporphyrin, oligothiophene, arylamine derivative, perylene derivative, hexacene hexaazatriphenylene derivative, quinacridone derivative, anthraquinone derivative, polyaniline-based conductive polymer, and polythiophene-based conductive polymer, but is not limited thereto.

[0166] As the hole transport layer material according to the present application, a material having a high hole mobility is preferred. Any one or more of the following structures can be selected: carbazole derivative, triarylamine derivative, diphenylamine derivative, fluorene derivative, stilbene derivative, phthalocyanine derivative, hexacene hexaazatriphenylene derivative, quinacridone derivative, anthraquinone derivative, polyaniline, polythiophene, polyvinylcarbazole, but is not limited thereto.

[0167] As the light emitting layer material of the present application, it includes a light emitting layer host material and a light emitting layer dopant material. The host material of the light emitting layer not only needs to have a bipolar charge transport property, but also needs to have a proper energy level to effectively transfer the excitation energy to the guest light emitting material, which can be selected from any one or more than one of the following structures: diphenyl styryl aryl derivatives, stilbene derivatives, carbazole derivatives, triarylamine derivatives, anthracene derivatives, and pyrene derivatives, etc. The dopant material can be selected from any one or more than one 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.

[0168] As the electron transport layer material of the present application, it is preferable to have a material with high electron mobility. It can be selected from any one or more than one of the following structures: metal chelates, oxazol derivatives, thiazole derivatives, diazole derivatives, azabenzene derivatives, diazanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, quinoline derivatives, phenanthroline derivatives, benzimidazole derivatives, etc., but not limited thereto.

[0169] As the electron injection layer material of the present application, it is preferable to have a material with good electron injection and transport effect. It can be selected from any one or more than one 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, other substances with high electron injection property. Examples can be listed as Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, etc., but not limited thereto.

[0170] As the cathode material of the present application, it is preferable to have a material with low work function. 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 (such as ITO, IZO, etc.); when the cathode is a semi-reflective electrode or a reflective electrode, it can be selected from any one or more than one of the following structures: 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 (such as a mixture of Ag and Mg), but not limited thereto.

[0171] As the cladding layer material of the present application, a material with high light extraction efficiency is preferred. In addition to the heterocyclic compound of the present application, any one or more of the following structures can be used: for example, metal halides, oxides, nitrides, oxynitrides, sulfides, selenides, aromatic hydrocarbon compounds, heteroaromatic hydrocarbon compounds, aromatic amine compounds, etc. can be used, but the present application is not limited thereto. Preferably, the cladding layer material uses the heterocyclic compound of the present application.

[0172] The preparation method of each layer of the organic electroluminescent device is not particularly limited, and can be formed by vacuum evaporation, spin coating, vapor deposition, blade coating, Langmuir-Blodgett printing, laser printing, laser-induced thermal imaging (LITI) method.

[0173] The organic electroluminescent device of the present application is widely used in panel display, lighting source, flexible OLED, electronic paper, organic solar cell, organic photoreceptor or organic thin film transistor, signboard, signal lamp and the like.

[0174] The present application also provides a preparation method of the compound represented by formula 1, but the preparation method of the present application is not limited thereto, and the following is only an example of the synthesis route. The reaction types described below are commonly used in organic synthesis, and the reaction conditions (for example, the selection of reaction solvents, catalysts, ligands, bases, etc., the amount used, and the order and method of addition) are not particularly limited, and conventional methods and operations can be used.

[0175] Synthesis route of the compound represented by formula 1:

[0176]

[0177] When Ar1, Ar2, Ar3 are all different:

[0178]

[0179] When -L1-Ar1 and -L3-Ar3 are the same:

[0180]

[0181] When -L2-Ar2 and -L3-Ar3 are the same:

[0182]

[0183] The X a , X b , X c , X d , X e , X f , X g , X h , X i, X j , X k , X l , X m , X n independently selected from any one of Cl, Br, I.

[0184] The present application is explained in more detail by the following examples, which further illustrate the technical solutions and technical effects of the present application, but are not intended to limit the present application. Based on the description, those skilled in the art will be able to implement the present application and prepare other compounds and devices according to the present application within the entire scope disclosed without any creative effort.

[0185] Description of raw materials, reagents and characterization equipment:

[0186] The present application does not have any particular limitation on the source of the raw materials used in the following examples, and commercially available products or raw materials obtained by using the preparation methods well known to those skilled in the art can be used.

[0187] Mass spectrometry uses a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer in the United Kingdom.

[0188] Elemental analysis uses a Vario EL cube organic elemental analyzer of Elementar Company in Germany.

[0189] Synthesis Example 1: Synthesis of Intermediate A-8

[0190]

[0191] Preparation of intermediate c-8:

[0192] Under nitrogen protection, a-8 (25.95 g, 150.00 mmol), b-8 (28.72 g, 150.00 mmol), K2CO3 (41.46 g, 300.00 mmol), Pd(PPh3)4 (1.85 g, 1.60 mmol), 800 mL of a mixture of toluene / ethanol / water (2:1:1) were added to a reaction bottle, the mixture was stirred, and the above reaction system was heated to reflux for 3 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, and separated by standing. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. Crystallization was performed by cooling, suction filtration was performed, and the obtained solid was recrystallized with toluene: ethanol = 10:3, and dried to obtain intermediate c-8 (31.28 g, 87%); HPLC purity ≧98.86%. Mass spectrum m / z: 239.0515 (theoretical value: 239.0502).

[0193] Preparation of intermediate A-8:

[0194] To a reaction flask was placed f-59 (24.50 g, 80.00 mmol), B2Pin2(22.85 g, 90.00 mmol), K2CO3(24.88 g, 180.00 mmol), Pd(PPh3)4(1.16 g, 1.00 mmol), DMF (450 mL) under nitrogen protection, and the above reaction system was heated to reflux for 4 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, and allowed to stand to separate, the organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained solid was recrystallized with toluene: ethanol = 10: 1, and dried to obtain intermediate B-59 (23.45 g, 83%), HPLC purity ≧ 99.25%. Mass spectrum m / z: 353.2162 (theoretical value: 353.2149).

[0195] According to the preparation method of intermediate A-8 in synthesis example 1, other intermediates required by the present application were prepared by replacing the raw materials accordingly, and the raw materials are shown in the following table:

[0196]

[0197]

[0198]

[0199] Synthesis example 2: preparation of intermediate B-59

[0200] To a reaction flask was placed f-59 (24.50 g, 80.00 mmol), B2Pin2(22.85 g, 90.00 mmol), K2CO3(24.88 g, 180.00 mmol), Pd(PPh3)4(1.16 g, 1.00 mmol), DMF (450 mL) under nitrogen protection, and the above reaction system was heated to reflux for 4 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, and allowed to stand to separate, the organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained solid was recrystallized with toluene: ethanol = 10: 1, and dried to obtain intermediate B-59 (23.45 g, 83%), HPLC purity ≧ 99.25%. Mass spectrum m / z: 353.2162 (theoretical value: 353.2149).

[0201] Synthesis example 3: preparation of intermediate B-161

[0202]

[0203] Following the procedure for the preparation of intermediate B-59 in synthesis example 2, f-59 was replaced by equimolar f-161, respectively, to give intermediate B-161 (26.26 g, 81%), HPLC purity > 99.08%. Mass spectrum m / z: 400.2225 (calcd: 400.2210).

[0204] Synthesis Example 5: Preparation of compound 8

[0205]

[0206] Preparation of intermediate D-8:

[0207] Under nitrogen protection, G-8 (25.39 g, 80.00 mmol), A-8 (26.50 g, 80.00 mmol), K2CO3 (22.11 g, 160.00 mmol), Pd(PPh3)4 (1.16 g, 1.00 mmol) and 400 mL of mixed solvent of toluene / ethanol / water (2:1:1) were added into a reaction bottle, and the above reaction system was heated to reflux for 5 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, and separated by standing. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. Crystallization was performed by cooling, and the obtained solid was recrystallized with toluene:methanol = 10:3 to give D-8 (24.94 g, 79%), HPLC purity > 99.67%. Mass spectrum m / z: 392.9912 (calcd: 392.9920).

[0208] Preparation of intermediate E-8:

[0209] Under nitrogen protection, D-8 (19.73 g, 50.00 mmol), B-8 (13.10 g, 50.00 mmol), K2CO3 (13.82 g, 100.00 mmol), Pd(dppf)Cl2 (0.48 g, 0.65 mmol) and 300 mL of mixed solvent of toluene / ethanol / water (2:1:1) were added into a reaction bottle, and the above reaction system was heated to reflux for 6 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, and separated by standing. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. Crystallization was performed by cooling, and the obtained solid was recrystallized with toluene:methanol = 10:1 to give E-8 (19.95 g, 75%), HPLC purity > 99.85%. Mass spectrum m / z: 531.1404 (calcd: 531.1390).

[0210] Preparation of compound 1:

[0211] Under nitrogen protection, E-8 (10.64 g, 20.00 mmol), C-8 (8.17 g, 20.00 mmol), K2CO3(5.53 g, 40.00 mmol), Pd2(dba)3(0.32 g, 0.35 mmol), P(t-Bu)3(0.14 g, 0.70 mmol) and 100 mL of a mixed solvent of toluene / ethanol / water (2:1:1) were heated to reflux for 8 h. After the reaction was completed, the reaction system was cooled to room temperature, distilled water was added, and dichloromethane was used for extraction. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The product was obtained by crystallization under cooling, and then recrystallized from toluene to obtain compound 8 (10.58 g, 68%), with an HPLC purity of ≧99.95%. Mass spectrum m / z: 777.2791 (theoretical value: 777.2780). Theoretical elemental content (%) C 57 H 35 N3O: C, 88.01; H, 4.54; N, 5.40. Actual elemental content (%): C, 88.05; H, 4.56; N, 5.37.

[0212] Synthesis Example 6: Preparation of compound 22

[0213]

[0214] According to the same preparation method as in synthesis example 5, A-8 was replaced by an equal molar amount of A-22, B-8 was replaced by an equal molar amount of B-22, and C-8 was replaced by an equal molar amount of C-22 to obtain compound 22 (9.65 g), with an HPLC purity of ≧99.98%. Mass spectrum m / z: 679.1961 (theoretical value: 679.1970). Theoretical elemental content (%) C 49 H 29 NOS: C, 86.57; H, 4.30; N, 2.06. Actual elemental content (%): C, 86.60; H, 4.28; N, 2.10.

[0215] Synthesis Example 7: Preparation of compound 37

[0216]

[0217] According to the same preparation method as in synthesis example 5, A-8 was replaced by an equal molar amount of A-37, B-8 was replaced by an equal molar amount of B-37, and C-8 was replaced by an equal molar amount of C-37 to obtain compound 37 (10.80 g), with an HPLC purity of ≧99.93%. Mass spectrum m / z: 805.2649 (theoretical value: 805.2635). Theoretical elemental content (%) C 56 H 40FNSSi: C, 83.44; H, 5.00; N, 1.74. Found ( ): C, 83.42; H, 4.99; N, 1.73.

[0218] Synthesis Example 8: Preparation of Compound 42

[0219]

[0220] Following the same preparation method as Synthesis Example 5, A-8 was replaced with an equivalent molar of A-42, B-8 was replaced with an equivalent molar of B-42, and C-8 was replaced with an equivalent molar of C-42 to obtain Compound 42 (9.91 g) with HPLC purity > 99.97%. Mass spectrum m / z: 707.3178 (theoretical value: 707.3188). Theoretical elemental content (%) C 53 H 41 NO: C, 89.92; H, 5.84; N, 1.98. Found elemental content (%) : C, 89.89; H, 5.88; N, 2.01.

[0221] Synthesis Example 9: Preparation of Compound 47

[0222]

[0223] Following the same preparation method as Synthesis Example 5, E-8 was replaced with an equivalent molar of E-42, and C-8 was replaced with an equivalent molar of C-47 to obtain Compound 47 (9.36 g) with HPLC purity > 99.99%. Mass spectrum m / z: 649.2421 (theoretical value: 649.2406). Theoretical elemental content (%) C 49 H 31 NO: C, 90.57; H, 4.81; N, 2.16. Found elemental content (%) : C, 90.61; H, 4.79; N, 2.18.

[0224] Synthesis Example 10: Preparation of Compound 59

[0225]

[0226] Following the same preparation method as Synthesis Example 5, A-8 was replaced with an equivalent molar of A-59, B-8 was replaced with an equivalent molar of B-59, and C-8 was replaced with an equivalent molar of C-59 to obtain Compound 59 (9.87 g) with HPLC purity > 99.95%. Mass spectrum m / z: 714.3612 (theoretical value: 714.3597). Theoretical elemental content (%) C 53 H 30D9NO: C, 89.04; H, 6.77; N, 1.96. Found (mass %): C, 89.06; H, 6.80; N, 1.95.

[0227] Synthesis Example 11: Preparation of compound 71

[0228]

[0229] According to the same preparation method as in the synthesis example 5, G-8 was replaced with an equivalent molar of G-71, A-8 was replaced with an equivalent molar of A-71, B-8 was replaced with an equivalent molar of B-42, C-8 was replaced with an equivalent molar of C-71, to obtain compound 71 (10.01 g), HPLC purity ≧ 99.96%. Mass spectrum m / z: 714.2658 (theoretical value: 714.2671). Theoretical elemental content (%) C 53 H 34 N2O: C, 89.05; H, 4.79; N, 3.92. Found (mass %): C, 89.10; H, 4.82; N, 3.88.

[0230] Synthesis Example 12: Preparation of compound 85

[0231]

[0232] According to the same preparation method as in the synthesis example 5, A-8 was replaced with an equivalent molar of A-85, B-8 was replaced with an equivalent molar of B-85, C-8 was replaced with an equivalent molar of C-85, to obtain compound 85 (9.46 g), HPLC purity ≧ 99.97%. Mass spectrum m / z: 675.2311 (theoretical value: 675.2311). Theoretical elemental content (%) C 49 H 29 N3O: C, 87.09; H, 4.33; N, 6.22. Found (mass %): C, 87.13; H, 4.29; N, 6.25.

[0233] Synthesis Example 13: Preparation of compound 123

[0234]

[0235] According to the same preparation method as in the synthesis example 5, D-8 was replaced with an equivalent molar of D-42, B-8 was replaced with an equivalent molar of d-146, C-8 was replaced with an equivalent molar of C-123, to obtain compound 123 (10.02 g), HPLC purity ≧ 99.98%. Mass spectrum m / z: 715.2349 (theoretical value 715.2334). Theoretical elemental content (%) C 53 H 33NS: C, 88.92; H, 4.65; N, 1.96. Found ( % ) : C, 88.89; H, 4.61; N, 2.01.

[0236] Synthesis Example 14: Preparation of compound 125

[0237]

[0238] Following the same preparation method as synthesis example 5, replace G-8 with equimolar of G-125, A-8 with equimolar of A-125, B-8 with equimolar of d-146, C-8 with equimolar of C-125, to obtain compound 125 (10.49 g) with HPLC purity > 99.96%. Mass spectrum m / z: 757.2817 (theoretical value: 757.2803). Theoretical elemental content (%) C 56 H 39 NS: C, 88.74; H, 5.19; N, 1.85. Found ( % ) : C, 88.77; H, 5.22; N, 1.83.

[0239] Synthesis Example 15: Preparation of compound 139

[0240]

[0241] Following the same preparation method as synthesis example 5, replace D-8 with equimolar of D-59, B-8 with equimolar of d-146, C-8 with equimolar of C-139, to obtain compound 139 (10.28 g) with HPLC purity > 99.95%. Mass spectrum m / z: 755.2293 (theoretical value 755.2283). Theoretical elemental content (%) C 53 H 33 NS: C, 87.39; H, 4.40; N, 1.85. Found ( % ) : C, 87.43; H, 4.37; N, 1.88.

[0242] Synthesis Example 16: Preparation of compound 146

[0243]

[0244] Following the same preparation method as synthesis example 5, replace D-8 with equimolar of D-42, B-8 with equimolar of B-146, C-8 with equimolar of C-146, to obtain compound 146 (10.63 g) with HPLC purity > 99.94%. Mass spectrum m / z: 781.2428 (theoretical value 781.2439). Theoretical elemental content (%) C 57 H 35NOS: C, 87.55; H, 4.51; N, 1.79. Found: C, 87.59; H, 4.49; N, 1.82.

[0245] Synthesis Example 17: Preparation of compound 149

[0246]

[0247] According to the same preparation method of synthesis example 5, E-8 was replaced by equimolar E-123, C-8 was replaced by equimolar C-149, compound 149 (10.11 g) was obtained, HPLC purity≧99.96%. Mass spectrum m / z: 721.1907 (theoretical value 721.1898). Theoretical elemental content (%) C 51 H 31 NS2: C, 84.85; H, 4.33; N, 1.94. Found: C, 84.88; H, 4.31; N, 1.97.

[0248] Synthesis Example 18: Preparation of compound 155

[0249]

[0250] Preparation of intermediate F-155:

[0251] Under nitrogen protection, G-155 (11.29 g, 50.00 mmol), B-8 (13.10 g, 50.00 mmol), K2CO3(13.82 g, 100.00 mmol), Pd(PPh3)4(0.69 g, 0.60 mmol) and 300 mL of a mixed solvent of toluene / ethanol / water (2:1:1) were added to a reaction bottle, and the above reaction system was heated to reflux for 5 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, and separated by standing. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. Crystallization was performed by cooling, suction filtration was performed, and the obtained solid was recrystallized with toluene to obtain F-155 (14.71 g, 81%), HPLC purity≧99.85%. Mass spectrum m / z: 362.0254 (theoretical value: 362.0265).

[0252] Preparation of compound 155:

[0253] A-55 (13.25 g, 40.00 mmol), K2CO3(11.06 g, 80.00 mmol), Pd2(dba)3(0.46 g, 0.50 mmol), P(t-Bu)3(0.20 g, 1.00 mmol) and 200 mL of a mixed solvent of toluene / ethanol / water (2:1:1) under nitrogen protection. The reaction was heated to reflux for 7 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, and separated by standing. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by reduced pressure distillation. The product was crystallized by cooling, filtered, and recrystallized from toluene to obtain compound 155 (9.95 g, 71%) with an HPLC purity of > 99.97%. Mass spectrum m / z: 700.2502 (theoretical value: 700.2515). Theoretical elemental content (%) C 52 H 32 N2O: C, 89.12; H, 4.60; N, 4.00. Found elemental content (%): C, 89.08; H, 4.57; N, 4.05.

[0254] Synthesis Example 19: Preparation of compound 160

[0255]

[0256] According to the same preparation method as in synthesis example 18, A-155 was replaced with an equal molar amount of A-160, and B-8 was replaced with an equal molar amount of B-160 to obtain compound 160 (10.89 g) with an HPLC purity of > 99.93%. Mass spectrum m / z: 800.2836 (theoretical value: 800.2828). Theoretical elemental content (%) C 60 H 36 N2O: C, 89.97; H, 4.53; N, 3.50. Found elemental content (%): C, 89.95; H, 4.56; N, 3.53.

[0257] Synthesis Example 20: Preparation of compound 161

[0258]

[0259] According to the same preparation method as in synthesis example 18, A-155 was replaced with an equal molar amount of A-161, and B-8 was replaced with an equal molar amount of B-161 to obtain compound 161 (10.56 g) with an HPLC purity of > 99.95%. Mass spectrum m / z: 764.3659 (theoretical value: 764.3643). Theoretical elemental content (%) C 56 H 32D8N2O: C, 87.92; H, 6.32; N, 3.66. Found (%): C, 87.96; H, 6.29; N, 3.68.

[0260] Synthesis Example 21: Preparation of Compound 173

[0261]

[0262] Following the same preparation procedure as in Synthesis Example 18, A-155 was replaced with an equivalent molar of A-173, and B-8 was replaced with an equivalent molar of B-173 to give Compound 173 (10.43 g) with HPLC purity > 99.97%. Mass spectrum m / z: 744.2616 (theoretical value: 744.2599). Theoretical elemental content (%) C 54 H 36 N2S: C, 87.06; H, 4.87; N, 3.76. Found (%): C, 87.10; H, 4.85; N, 3.77.

[0263] Synthesis Example 22: Preparation of Compound 193

[0264]

[0265] Following the same preparation procedure as in Synthesis Example 18, A-155 was replaced with an equivalent molar of A-193, and B-8 was replaced with an equivalent molar of B-193 to give Compound 193 (10.58 g) with HPLC purity > 99.96%. Mass spectrum m / z: 766.2433 (theoretical value: 766.2443). Theoretical elemental content (%) C 56 H 34 N2S: C, 87.70; H, 4.47; N, 3.65. Found (%): C, 87.68; H, 4.45; N, 3.64.

[0266] Synthesis Example 23: Preparation of Compound 222

[0267]

[0268] Following the same preparation procedure as in Synthesis Example 18, A-155 was replaced with an equivalent molar of A-42, and B-8 was replaced with an equivalent molar of B-42 to give Compound 222 (9.95 g) with HPLC purity > 99.97%. Mass spectrum m / z: 700.2500 (theoretical value: 700.2515). Theoretical elemental content (%) C 52 H 32N2O: C, 89.12; H, 4.60; N, 4.00. Found: C, 89.18; H, 4.57; N, 3.99.

[0269] Synthesis Example 24: Preparation of compound 229

[0270]

[0271] Following the same preparation procedure as in Synthesis Example 18, A-155 was replaced with an equivalent molar of A-229, B-8 was replaced with an equivalent molar of B-229 to give compound 229 (10.32 g) with HPLC purity > 99.96%. Mass spectrum m / z: 736.2342 (calc. 736.2326). Theoretical elemental content (%) C 52 H 30 F2N2O: C, 84.77; H, 4.10; N, 3.80. Found: C, 84.75; H, 4.11; N, 3.78.

[0272] Synthesis Example 25: Preparation of compound 244

[0273]

[0274] Following the same preparation procedure as in Synthesis Example 18, G-155 was replaced with an equivalent molar of G-244, A-155 was replaced with an equivalent molar of A-244, and B-8 was replaced with an equivalent molar of B-42 to give compound 244 (9.99 g) with HPLC purity > 99.97%. Mass spectrum m / z: 703.2715 (calc. 703.2703). Theoretical elemental content (%) C 52 H 29 D3N2O: C, 88.74; H, 5.01; N, 3.98. Found: C, 88.71; H, 5.04; N, 4.01.

[0275] Synthesis Example 26: Preparation of compound 271

[0276]

[0277] Following the same preparation procedure as in Synthesis Example 18, F-155 was replaced with an equivalent molar of F-222, A-155 was replaced with an equivalent molar of A-271 to give compound 271 (9.84 g) with HPLC purity > 99.95%. Mass spectrum m / z: 702.2402 (calc. 702.2420). Theoretical elemental content (%) C 50 H 30N4O: C, 85.45; H, 4.30; N, 7.97. Found: C, 85.46; H, 4.27; N, 8.03.

[0278] Synthesis Example 27: Preparation of compound 290

[0279]

[0280] Following the same preparation procedure as in synthesis example 18, A-155 was replaced with an equivalent molar of A-290, B-8 was replaced with an equivalent molar of B-85 to give compound 290 (9.92 g) with HPLC purity > 99.94%. Mass spectrum m / z: 708.2779 (calc. 708.2796). Theoretical elemental content (%) C 50 H 24 D6N4O: C, 84.72; H, 5.12; N, 7.90. Found: C, 84.69; H, 5.16; N, 7.92.

[0281] Synthesis Example 28: Preparation of compound 305

[0282]

[0283] Following the same preparation procedure as in synthesis example 18, G-155 was replaced with an equivalent molar of G-305, A-155 was replaced with an equivalent molar of A-42, B-8 was replaced with an equivalent molar of d-146 to give compound 305 (10.04 g) with HPLC purity > 99.96%. Mass spectrum m / z: 716.2296 (calc. 716.2286). Theoretical elemental content (%) C 52 H 32 N2S: C, 87.12; H, 4.50; N, 3.91. Found: C, 87.08; H, 4.55; N, 3.89.

[0284] Synthesis Example 29: Preparation of compound 313

[0285]

[0286] Following the same preparation procedure as in synthesis example 18, A-155 was replaced with an equivalent molar of A-59, B-8 was replaced with an equivalent molar of d-146 to give compound 313 (10.18 g) with HPLC purity > 99.97%. Mass spectrum m / z: 716.2298 (calc. 716.2286). Theoretical elemental content (%) C 52 H 32N2S: C, 87.12; H, 4.50; N, 3.91. Found (mass %): C, 87.15; H, 4.53; N, 3.87.

[0287] Synthesis Example 30: Preparation of compound 342

[0288]

[0289] Following the same preparation method as synthesis example 18, F-155 was replaced with equimolar F-313, A-155 was replaced with equimolar A-342, to give compound 342 (10.09 g) with HPLC purity > 99.95%. Mass spectrum m / z: 720.2083 (theoretical value: 720.2096). Theoretical elemental content (%) C 48 H 28 N6S: C, 79.98; H, 3.92; N, 11.66. Found elemental content (%) C, 80.02; H, 3.94; N, 11.63.

[0290] Synthesis Example 31: Preparation of compound 355

[0291]

[0292] Following the same preparation method as synthesis example 18, A-155 was replaced with equimolar A-42, B-8 was replaced with equimolar B-355, to give compound 355 (10.84 g) with HPLC purity > 99.94%. Mass spectrum m / z: 796.2861 (theoretical value: 796.2850). Theoretical elemental content (%) C 58 H 32 D4N2S: C, 87.40; H, 5.06; N, 3.51. Found elemental content (%) C, 87.45; H, 5.05; N, 3.49.

[0293] Synthesis Example 32: Preparation of compound 365

[0294]

[0295] Following the same preparation method as synthesis example 18, A-155 was replaced with equimolar B-8, B-8 was replaced with equimolar A-365, to give compound 365 (10.56 g) with HPLC purity > 99.95%. Mass spectrum m / z: 764.2454 (theoretical value: 764.2464). Theoretical elemental content (%) C 56 H 32N2O2: C, 87.94; H, 4.22; N, 3.66. Found ( % ): C, 87.96; H, 4.26; N, 3.62.

[0296] Synthesis Example 33: Preparation of Compound 367

[0297]

[0298] Following the same preparation procedure as in Synthesis Example 5, A-8 was replaced with an equivalent molar of A-367, B-8 was replaced with an equivalent molar of B-367, and C-8 was replaced with an equivalent molar of C-367 to give Compound 367 (10.47 g) with HPLC purity > 99.94%. Mass spectrum m / z: 769.2453 (theoretical value: 769.2439). Theoretical elemental content (%) C 56 H 35 NOS: C, 87.36; H, 4.58; N, 1.82. Found ( % ): C, 87.33; H, 4.62; N, 1.85.

[0299] Synthesis Example 34: Preparation of Compound 407

[0300]

[0301] Following the same preparation procedure as in Synthesis Example 18, A-155 was replaced with an equivalent molar of B-42, and B-8 was replaced with an equivalent molar of A-42 to give Compound 407 (10.14 g) with HPLC purity > 99.98%. Mass spectrum m / z: 713.2342 (theoretical value: 713.2355). Theoretical elemental content (%) C 53 H 31 NO2: C, 89.18; H, 4.38; N, 1.96. Found ( % ): C, 89.21; H, 4.42; N, 1.94.

[0302] Synthesis Example 35: Preparation of Compound 424

[0303]

[0304] Following the same preparation procedure as in Synthesis Example 18, A-155 was replaced with an equivalent molar of B-42, and B-8 was replaced with an equivalent molar of A-424 to give Compound 424 (10.90 g) with HPLC purity > 99.97%. Mass spectrum m / z: 789.2683 (theoretical value: 789.2668). Theoretical elemental content (%) C 59 H 35NO2: C, 89.71 ; H, 4.47; N, 1.77. Found ( % ) : C, 89.66; H, 4.50; N, 1.78.

[0305] Synthesis Example 36: Preparation of compound 479

[0306]

[0307] Following the same preparation procedure as in Synthesis Example 18, G-155 was replaced with an equivalent molar of G-479, A-155 was replaced with an equivalent molar of d-146, and B-8 was replaced with an equivalent molar of A-479 to give compound 479 (10.39 g) with HPLC purity > 99.96%. Mass spectrum m / z: 763.1820 (theoretical value: 763.1804). Theoretical elemental content (%) C 53 H 30 FNS2: C, 83.33; H, 3.96; N, 1.83. Found ( % ) : C, 83.35; H, 3.97; N, 1.86.

[0308] Synthesis Example 37: Preparation of compound 495

[0309]

[0310] Following the same preparation procedure as in Synthesis Example 18, A-155 was replaced with an equivalent molar of B-204, and B-8 was replaced with an equivalent molar of A-495 to give compound 495 (11.42 g) with HPLC purity > 99.93%. Mass spectrum m / z: 851.1763 (theoretical value: 851.1775). Theoretical elemental content (%) C 59 H 33 NS3: C, 83.17; H, 3.90; N, 1.64. Found ( % ) : C, 83.21 ; H, 3.88; N, 1.65.

[0311] Synthesis Example 38: Preparation of compound 506

[0312]

[0313] Following the same preparation procedure as in Synthesis Example 18, A-8 was replaced with an equivalent molar of A-506, B-8 was replaced with an equivalent molar of d-146, and C-8 was replaced with an equivalent molar of B-42 to give compound 506 (10.09 g) with HPLC purity > 99.96%. Mass spectrum m / z: 730.2091 (theoretical value: 730.2079). Theoretical elemental content (%) C 52 H 30N2OS: C, 83.45; H, 4.14; N, 3.83. Found (mass %): C, 83.47; H, 4.11; N, 3.81.

[0314] [Device Example 1]

[0315] First, a glass substrate on which ITO / Ag / ITO was deposited was cleaned in distilled water twice, ultrasonically washed for 30 minutes, and then cleaned in distilled water repeatedly twice, ultrasonically washed for 10 minutes. After the cleaning in distilled water, the substrate was dried on a hot plate heated to 120°C, and then transferred to a plasma cleaner. After washing for 5 minutes, the substrate was transferred to a deposition machine.

[0316] Then, HI was vacuum-deposited on the cleaned ITO / Ag / ITO substrate as a hole injection layer, with a thickness of 14 nm. HT was vacuum-deposited on the hole injection layer as a hole transport layer, with a thickness of 75 nm. RH was vacuum-deposited on the hole transport layer as a host material, and RD was vacuum-deposited as a dopant material (mass ratio of 97:3) to form a light-emitting layer, with a thickness of 40 nm. ET and Liq (mass ratio of 1:1) were vacuum-deposited on the light-emitting layer as an electron transport layer, with a thickness of 35 nm. LiF was vacuum-deposited on the electron transport layer as an electron injection layer, with a thickness of 1 nm. Then, Mg:Ag (mass ratio of 1:9) was vacuum-deposited on the electron injection layer as a cathode, with a thickness of 10 nm. Compound 8 of the present application was vacuum-deposited on the cathode as a capping layer, with a thickness of 70 nm. Thus, an organic electroluminescent device 1 was prepared.

[0317]

[0318] Device Examples 2 to 34 were prepared in the same manner as in Device Example 1, except that Compound 22, Compound 37, Compound 42, Compound 47, Compound 59, Compound 71, Compound 85, Compound 123, Compound 125, Compound 139, Compound 146, Compound 149, Compound 155, Compound 160, Compound 161, Compound 173, Compound 193, Compound 222, Compound 229, Compound 244, Compound 271, Compound 290, Compound 305, Compound 313, Compound 342, Compound 355, Compound 365, Compound 367, Compound 407, Compound 424, Compound 479, Compound 495, and Compound 506 of the present application were used instead of Compound 8 of Device Example 1 as a capping layer.

[0319] [Comparative Device Examples 1 and 2]

[0320] Comparative Device 1-2 were prepared by using CP-1 and CP-2 instead of compound 8 in Device Device Example 1 as the cover layer, and other preparation steps were the same as Device Example 1.

[0321] A combined IVL test system was composed of test software, computer, K2400 digital source meter produced by Keithley Company of USA and PR788 spectral scanning luminance meter produced by Photo Research Company of USA to test the driving voltage and luminous efficiency of the organic light emitting device. The life test was carried out by using M6000 OLED life test system produced by McScience Company. The test environment was atmospheric environment and the temperature was room temperature. The test results of the luminescent characteristics of the organic electroluminescent device obtained in Device Examples 1-34 and Comparative Examples 1-2 of the present application are shown in Table 1.

[0322] [Table 1] Luminescent characteristics test of organic electroluminescent device

[0323]

[0324]

[0325] Note: T97 refers to the time used for the device brightness to decay to 97% under the current density of 10 mA / cm 2 ; T100 refers to the time used for the device brightness to decay to 100% under the current density of 10 mA / cm

[0326] From the results in Table 1, it can be seen that compared with Comparative Device 1-2, the heterocyclic compound of the present application applied to the organic electroluminescent device as the cover layer material can improve the light extraction efficiency of the organic electroluminescent device, and the luminous efficiency and service life of the device are significantly improved.

[0327] It should be noted that the present application is particularly described by individual embodiments, and for those skilled in the art, some improvements and modifications can be made to the present application without departing from the principles of the present application, and these improvements and modifications also fall within the protection scope of the present application.

Claims

1. A heterocyclic compound, characterized in that, The heterocyclic compound is represented by the structure shown in Formula 1: Ar1 is selected from formula 2: R1 is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C6 alkyl groups; The R2 is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl; The value of 'a' is selected from 0, 1, 2, or 3; when there are two or more R1s, the two or more R1s are the same as or different from each other; The value of c is selected from 0, 1, 2, 3, 4, 5 or 6; when there are two or more R2s, the two or more R2s are the same as or different from each other; The Ar2 is selected from formula 3: Equation 3 is selected from any of the following structures: The Y is selected from O or S; The R9 is selected from hydrogen, deuterium, cyano, halogen, or any of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; The d2 is selected from 0, 1, 2, 3, 4, 5 or 6; the d3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the d4 is selected from 0, 1, 2 or 3; the d5 is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R9s, the two or more R9s are the same as or different from each other; The Ar3 is selected from Formula 2 or any of the following structures: Y1 is selected from O, S, C(R5)2 or NR6; Y2 is selected from O or S; R3 and R4 are independently selected from hydrogen, deuterium, cyano, halogen, or any of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, camphene, norbornyl, phenyl, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl; The R5 is independently selected from any one of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, naphthyl; The R6 is independently selected from any one of the following groups, whether substituted or unsubstituted: phenyl, biphenyl, naphthyl; b1 is selected from 0, 1, 2, 3, 4 or 5; b2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; b4 is selected from 0, 1, 2, 3 or 4; b7 is selected from 0, 1, 2 or 3; b9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; when there are two or more R3 and R4, the two or more R3 and R4 are the same as or different from each other; The L1 is selected from a single bond or any of the following structures: The L2 is selected from a single bond or any of the following structures: The R 10 R 11 The group is independently selected from hydrogen, deuterium, cyano, halogen, or any of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; The R e Selected from hydrogen, deuterium, or any of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; e1 is selected from 0, 1, 2, 3, or 4; e2 is selected from 0, 1, 2, or 3; e3 is selected from 0, 1, or 2; e4 is selected from 0, 1, 2, 3, 4, 5, or 6; e5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; when there are two or more R... 10 At that time, two or more R 10 They are the same as or different from each other; The L3 is selected from a single bond or any of the following structures: The R a The group is independently selected from hydrogen, deuterium, cyano, halogen, or any of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; The R a The substituents in "substituted or unsubstituted" are selected from deuterium and halogens; The n1 is selected from 0, 1, 2, 3, or 4; the n2 is selected from 0, 1, 2, or 3; the n3 is selected from 0, 1, or 2; when there are two or more R... a At that time, two or more R a They are the same as or different from each other; Except R a In addition, the substituents represented by "substituted or unsubstituted" in the other groups include the following groups: deuterium, tritium, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, propyl, and butyl.

2. The heterocyclic compound according to claim 1, characterized in that, The R2 is selected from hydrogen, deuterium, cyano, halogen, or any of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, phenyl, pyridyl.

3. A heterocyclic compound according to claim 1, characterized in that, Equation 3 is selected from any of the following structures: The R9 is selected from hydrogen and deuterium.

4. A heterocyclic compound according to claim 1, characterized in that, The Ar3 is selected from Formula 2 or any of the following structures: The Y1 is selected from O, S or C(R5)2; R3 and R4 are independently selected from hydrogen, deuterium, cyano, halogen, or any of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, adamantyl, trimethylsilyl, triethylsilyl, tritert-butylsilyl. The R5 is independently selected from any one of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl.

5. A heterocyclic compound according to claim 1, characterized in that, The L1 is selected from a single bond or any of the following structures: The L2 is selected from a single bond or any of the following structures: The R 10 Independently selected from hydrogen and deuterium.

6. A heterocyclic compound, characterized in that, 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, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, characterized in that, The organic layer contains one or more of the heterocyclic compounds described in any one of claims 1 to 6.

8. An organic electroluminescent device according to claim 7, characterized in that, The organic layer includes a capping layer, which contains one or more of the heterocyclic compounds according to any one of claims 1 to 6.

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