A compound containing a heterocyclic ring and an organic electroluminescent device thereof

Abstract

The present invention provides a compound containing a heterocycle and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The present invention proposes a compound with high electron mobility, high triplet energy level and wide energy gap, which can obtain an organic electroluminescent device with low driving voltage, high luminous efficiency and long life. Since it is easy to transmit electrons, the transmission of holes and electrons can be balanced, thereby improving the luminous efficiency of the device, and can also avoid the diffusion of excitons to adjacent functional layers, effectively improving the driving voltage and luminous efficiency of the organic electroluminescent device, thereby extending the life of the device; at the same time, the compound containing a heterocycle provided by the present invention has a higher glass transition temperature, which can improve the film forming property and thermal stability of the material and extend the life of the device; in addition, the compound containing a heterocycle also has a higher refractive index, which can effectively improve the light extraction efficiency, thereby improving the luminous efficiency of the device.

Description

Technical Field

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

[0002] With the rise of technologies such as 8K, 5G, AI, AR / VR, new display technology paths are diversified and continue to develop in the direction of miniaturization, high definition, low power consumption, and flexibility. Organic Light Emitting Diodes (OLEDs) are considered to be a very promising new generation of display technology and have been deeply studied due to their many advantages such as self-luminescence, wide viewing angle, fast response speed, high definition, high brightness, and good flexibility. They are widely used in flat panel displays and solid-state lighting.

[0003] Organic light-emitting diodes are carrier dual-injection devices that convert electrical energy into light energy. The light-emitting process is that under the action of an external electric field, the holes generated by the anode material and the electrons generated by the cathode material are respectively injected into the OLED device. After the holes are injected, they are transmitted at the HOMO energy level, and after the electrons are injected, they are transmitted at the LUMO energy level. After the holes and electrons are transmitted into the organic light-emitting layer, they recombine to form excitons. The excitons transfer energy to the organic light-emitting molecules in the light-emitting layer, and these molecules transition from the ground state to the excited state due to the energy they gain. The molecules in the excited state are very unstable and will return to the ground state by radiation transition. During the transition process, the energy is released in the form of light energy, generating electroluminescence. Since the development of organic light-emitting diodes, single-layer, double-layer and multi-layer structures have been applied. At present, most typical devices are composed of anodes, hole injection layers, hole transport layers, electron blocking layers, light-emitting layers, hole blocking layers, electron transport layers, electron injection layers, cathodes and other multi-layer structures.

[0004] In recent years, the research and development of OLED devices has shown a rapid growth trend. At the same time, people's requirements for the performance of OLED products are getting higher and higher. There is still a lot of work to be done to further improve the performance of OLED devices and related basic research. Among the existing organic materials, the hole mobility of hole transport materials is better than the electron mobility of electron transport materials, and hole injection is easier than electron injection. Therefore, the electrons and holes injected from both sides of the electrode will recombine at a position closer to the cathode interface. The metal cathode will have a quenching effect on the nearby excitons, greatly reducing the efficiency of the device; the unbalanced transmission of the two carriers of electrons and holes will cause a decrease in the probability of exciton recombination, which also affects the photoelectric performance of the device. In addition, the light extraction efficiency of organic electroluminescent devices is generally low, which makes it difficult to improve the luminous efficiency. Therefore, in order to better balance the carriers, improve the light extraction efficiency, and optimize the device performance, it is urgent to design a new material with good electron mobility, which can enable electrons to be transferred to the light-emitting layer; prevent holes from escaping from the light-emitting layer, so that the carriers can recombine in the center of the light-emitting layer; improve the light extraction efficiency, thereby improving the luminous efficiency and service life of the device. Summary of the invention

[0005] In view of the above problems existing in the prior art, the present invention provides a compound containing a heterocyclic ring and an organic electroluminescent device thereof, which solves the problems of high driving voltage, low luminous efficiency, short life and the like of the organic electroluminescent device. Specifically, the technical solution of the present invention is as follows:

[0006] The present invention provides a compound containing a heterocycle, wherein the compound containing a heterocycle has a structure as shown in Formula I:

[0007]

[0008] In formula I, E is selected from any one of substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, and substituted or unsubstituted anthracenyl;

[0009] The A is selected from the group shown in the following formula I-1 or formula I-2:

[0010]

[0011] The R1 and R2 are independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or any one of R1 and R2 can be directly bonded to L; or R1 and R2 can be combined with each other to form a substituted or unsubstituted spiro ring;

[0012] The R3 is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R3 can be combined to form a substituted or unsubstituted ring;

[0013] Said a0 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0014] The Z is independently selected from any one of a single bond, O, S, C(Rx)(Ry), and N(Rz);

[0015] The Rx, Ry, and Rz are independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0016] The L is independently selected from a single bond or any one of the following groups:

[0017]

[0018] Said X is independently selected from C(R4) or N atom;

[0019] The R4 is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, or two adjacent R4 can be combined to form a substituted or unsubstituted ring;

[0020] Said n1 and n2 are independently selected from 0 or 1;

[0021] The Y is selected from any one of O and S.

[0022] The present invention also provides an organic electroluminescent device, comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside at least one of the anode and the cathode, and the organic layer comprises any one or more of the heterocyclic compounds described in the present invention.

[0023] Beneficial Effects

[0024] The compound containing heterocycle provided by the present invention contains a conjugated larger fused group, so that it has high electron mobility, is easy to transmit electrons, can balance the transmission of holes and electrons, and thus improve the luminous efficiency of the device; at the same time, the compound of the present invention has a high triplet energy level and a wide energy gap. When the compound of the present invention is applied to the electron transport layer / hole blocking layer, the diffusion of excitons to the adjacent functional layer is minimized, and the driving voltage and luminous efficiency of the organic electroluminescent device can be improved, thereby extending the life of the device. The compound containing heterocycle of the present invention has a higher glass transition temperature, can improve the film forming property and thermal stability of the material, and when it is applied to the organic electroluminescent device, the life of the device can be extended. At the same time, the compound containing heterocycle has a higher refractive index. When it is applied to the covering layer of the organic electroluminescent device, the light extraction efficiency can be effectively improved, thereby improving the luminous efficiency of the device. DETAILED DESCRIPTION

[0025] The following will be a clear and complete description of the technical solutions in conjunction with the specific embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative work are within the scope of protection of the present invention.

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

[0027] In this specification, "*" means a part connected to another substituent. "*" can be connected to any optional position of the connected group / fragment. Can be expressed And so on.

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

[0029] Examples of the halogen atom described in the present invention may include fluorine, chlorine, bromine and iodine.

[0030] The alkyl group of the present invention refers to a monovalent group obtained by removing a hydrogen atom from an alkane molecule, which can be a straight chain alkyl group or a branched chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The alkyl group can be substituted or unsubstituted. Specific examples may include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, etc., but are not limited thereto.

[0031] The cycloalkyl group of the present invention refers to a monovalent group obtained by removing a hydrogen atom from a cyclic alkane molecule, preferably having 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 6 carbon atoms. The cycloalkyl group may be substituted or unsubstituted. Specific examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, etc., but are not limited thereto.

[0032] The aryl group of the present invention refers to a monovalent group obtained by removing a hydrogen atom from the aromatic carbon of the aromatic compound molecule, which can be a monocyclic aryl group, a polycyclic aryl group or a condensed ring aryl group, preferably having 6 to 60 carbon atoms, more preferably 6 to 30 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The aryl group includes a monocyclic aryl group, a polycyclic aryl group, a condensed ring aryl group, and the like. The aryl group can be substituted or unsubstituted. Specific examples may include phenyl, biphenyl, terphenyl, quaterphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, benzofluorenyl, triphenylene, fluoranthenyl, 9,9'-spirobifluorenyl, etc., but are not limited thereto.

[0033] The heteroaryl group of the present invention refers to a general term for a group in which one or more aromatic carbon atoms in an aromatic group are replaced by heteroatoms, wherein the heteroatoms include but are not limited to oxygen, sulfur, nitrogen, silicon or phosphorus atoms, preferably having 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, and most preferably 2 to 12 carbon atoms. The attachment site of the heteroaryl group may be located on a ring-forming carbon atom or on a ring-forming heteroatom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a condensed ring heteroaryl group, etc. The heteroaryl group may be substituted or unsubstituted. Specific examples may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinazolinyl, quinoxalinyl, benzoquinazolinyl, benzoquinoxalinyl, o-phenanthroline, naphthyridinyl, indolyl, benzothiophenyl, benzofuroyl, The invention also includes thiazolyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, naphthofuranyl, phenanthrobenzofuranyl, naphthiophenyl, phenanthrothiophenyl, naphthoxazolyl, naphthioimidazolyl, naphthiothiophenyl, phenanthroxazolyl, phenanthrothiophenyl, phenanthroimidazolyl, carbazolyl, benzocarbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiol, spirofluorenyloxanthracenyl, spirofluorenylthioxanthracenyl and the like, but is not limited thereto.

[0034] The aliphatic ring described in the present invention refers to a cyclic hydrocarbon with aliphatic properties, containing a closed carbon ring in the molecule, preferably having 3 to 60 carbon atoms, more preferably 3 to 30 carbon atoms, further preferably 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. It can form a monocyclic hydrocarbon or a polycyclic hydrocarbon, and can be completely unsaturated or partially unsaturated. It can further be a C3-30 cycloalkane, preferably a C3-18 cycloalkane, more preferably a C3-C12 cycloalkane, and most preferably a C3-C7 cycloalkane. It can further be a C3-30 cycloalkene, preferably a C3-18 cycloalkene, more preferably a C3-C12 cycloalkene, and most preferably a C3-C7 cycloalkene. It can further be a C3-30 cycloalkyne, preferably a C3-18 cycloalkyne, more preferably a C3-C12 cycloalkyne, and most preferably a C3-C7 cycloalkyne. The aliphatic ring can be substituted or unsubstituted. Specific examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclobutene, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited thereto. Multiple monocyclic hydrocarbons can also be connected in a variety of ways: two rings in a molecule can share a carbon atom to form a spirocycle; two carbon atoms on a ring can be connected by a carbon bridge to form a bridged ring; and several rings can also be connected to each other to form a cage-like structure.

[0035] The arylene group in the present invention refers to an aryl group having two bonding positions, i.e., a divalent group. Except that each of them is a divalent group, the above description of the aryl group is applicable.

[0036] The heteroarylene group in the present invention means a heteroaryl group having two bonding positions, i.e., a divalent group. Except that each of them is a divalent group, the above description of the heteroaryl group is applicable.

[0037] The term "substituted..." as used herein, such as "substituted alkyl, substituted cycloalkyl, substituted aryl, substituted heteroaryl, substituted arylene, substituted heteroarylene" refers to independently being mono- or poly-substituted by the following groups: deuterium, cyano, nitro, halogen atoms, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 Heterocycloalkyl, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C2~C30 heteroaryl, substituted or unsubstituted C1~C12 alkoxy, substituted or unsubstituted C1~C12 alkylthio, substituted or unsubstituted C1~C12 alkylamino, substituted or unsubstituted C6~C30 aryloxy, substituted or unsubstituted C6~C30 arylamino, etc., but not limited to these, or two adjacent substituents can be connected to form a ring. Preferably, the following radicals are mono- or polysubstituted: deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, peryl, pyrenyl, benzyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9'-spirobifluorenyl, diphenylamino, pyridyl, pyrimidinyl, triazine, carbazolyl, acridinyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, phenothiazinyl, phenoxazinyl, indolyl, etc., but are not limited thereto.

[0038] The "spirocyclic structure" of the present invention refers to a structure in which two carbon rings share one carbon atom, and preferably has 15 to 60 carbon atoms, more preferably 15 to 30 carbon atoms. Specifically, the spirocyclic structure may include any of the following substituted or unsubstituted groups:

[0039]

[0040] For example, when the spirocyclic structure is combined with fluorene, any of the substituted or unsubstituted groups of the following structural formulas may be formed:

[0041]

[0042] The term "connected to form a ring" used in the present invention refers to two groups connected to each other by a chemical bond and optionally aromatized. For example:

[0043]

[0044] In the present invention, the ring formed by connection can be an aromatic ring system, an aliphatic ring system or a ring system formed by the fusion of the two. The ring formed by connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring or a condensed ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanebenzophenone, cyclohexene, cyclohexane, cyclohexanebenzophenone, fluorene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.

[0045] The present invention provides a compound containing a heterocycle, wherein the compound containing a heterocycle has a structure as shown in Formula I:

[0046]

[0047] In formula I, E is selected from any one of substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, and substituted or unsubstituted anthracenyl;

[0048] The A is selected from the group shown in the following formula I-1 or formula I-2:

[0049]

[0050] The R1 and R2 are independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or any one of R1 and R2 can be directly bonded to L; or R1 and R2 can be combined with each other to form a substituted or unsubstituted spiro ring;

[0051] The R3 is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R3 can be combined to form a substituted or unsubstituted ring;

[0052] Said a0 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0053] The Z is independently selected from any one of a single bond, O, S, C(Rx)(Ry), and N(Rz);

[0054] The Rx, Ry, and Rz are independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0055] The L is independently selected from a single bond or any one of the following groups:

[0056]

[0057] Said X is independently selected from C(R4) or N atom;

[0058] The R4 is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, or two adjacent R4 can be combined to form a substituted or unsubstituted ring;

[0059] Said n1 and n2 are independently selected from 0 or 1;

[0060] The Y is selected from any one of O and S.

[0061] Preferably, E is selected from any one of the following groups:

[0062]

[0063] The R5 is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0064] The m1 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, and the m2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;

[0065] * indicates the fusion site.

[0066] Preferably, the Any one selected from the following groups:

[0067]

[0068] Preferably, R5 is independently selected from hydrogen, deuterium, cyano, or substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, pyridyl, phenyl-pyridyl, pyrimidyl, phenyl-pyrimidyl, pyrazinyl, phenyl-pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl;

[0069] The "substituted" group is selected from any one or more of deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl; when there are multiple substituents, the multiple substituents are the same or different from each other;

[0070] The m1 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, and the m2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0071] Preferably, R1 and R2 are independently selected from hydrogen, deuterium, or substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl;

[0072] The "substituted" group is selected from any one or more of deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, and when there are multiple substituents, the multiple substituents are the same or different from each other;

[0073] Or any one of R1 and R2 can be directly bonded to L; or R1 and R2 can be combined with each other to form any one of the following structures:

[0074]

[0075] The R6 is independently selected from deuterium, cyano, or substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl;

[0076] The "substituted" group is selected from any one or more of deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, and when there are multiple substituents, the multiple substituents are the same or different from each other;

[0077] The a1 is independently selected from 0, 1, 2, 3 or 4, the a2 is independently selected from 0, 1, 2, 3, 4, 5 or 6, the a3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the a4 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, the a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; the a6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14. The a7 is selected from 0, 1 or 2.

[0078] Preferably, the R3 is independently selected from hydrogen, deuterium, cyano, or any of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl; or two adjacent R3 can be combined to form any of a substituted or unsubstituted benzene ring, a naphthalene ring, or a C3-C7 aliphatic ring;

[0079] The "substituted" group is selected from any one or more of deuterium, substituted or unsubstituted C1-C12 alkyl, and substituted or unsubstituted C3-C12 cycloalkyl. When multiple substituents exist, the multiple substituents are the same or different from each other.

[0080] More preferably, the A is independently selected from any one of the following groups:

[0081]

[0082]

[0083] The R3 is independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, deuterium Substituted groups: any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, pyridyl, pyrimidyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl;

[0084] The R6 is independently selected from any one of hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinoxalinyl, and quinazolinyl;

[0085] The a0 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the a1 is independently selected from 0, 1, 2, 3 or 4, the a2 is independently selected from 0, 1, 2, 3, 4, 5 or 6, the a3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the a4 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, the a5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; a6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14, a7 is selected from 0, 1 or 2, a8 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7, a9 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13, a 10 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said a 11 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, said a 12 Independently selected from 0, 1, 2, 3, 4 or 5.

[0086] Preferably, Rx and Ry are independently selected from any one of hydrogen, deuterium, cyano, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornyl, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexanyl, phenyl, biphenyl, terphenyl, deuterated phenyl, deuterated biphenyl, naphthyl, deuterated naphthyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexanyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinazolinyl, and quinoxalinyl.

[0087] Preferably, the Rz is independently selected from any one of phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexanyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinazolinyl, and quinoxalinyl.

[0088] Preferably, the L is independently selected from a single bond or any one of the following substituted or unsubstituted groups:

[0089]

[0090]

[0091] The "substituted" group is selected from any one or more of deuterium, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, and norbornane; when multiple substituents exist, the multiple substituents are the same or different from each other.

[0092] Most preferably, the compound containing a heterocycle is selected from any one of the following structures:

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104] Some specific structural forms of the compounds of formula I described in the present invention are listed above, but the present invention is not limited to these chemical structures listed. All compounds based on the structure shown in chemical formula I and having substituents as defined above should be included.

[0105] The present invention also provides an organic electroluminescent device, comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside at least one of the anode and the cathode, and is characterized in that the organic layer comprises any one or more of the heterocyclic compounds described in the present invention.

[0106] Preferably, the organic electroluminescent device described in the present invention may include one or more organic layers, and the organic layers may include a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer and a covering layer, etc. Specifically, the organic layer located between the anode and the cathode may include a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer and the like, and the organic layer located on the outside of at least one of the electrodes of the anode and the cathode may include a covering layer and the like.

[0107] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes at least one of an electron transport layer or a hole blocking layer, and at least one of the electron transport layer or the hole blocking layer includes any one or more of the heterocyclic compounds described in the present invention.

[0108] More preferably, the organic layer comprises an electron transport layer, and the electron transport layer comprises any one or more of the heterocyclic compounds described in the present invention.

[0109] More preferably, the organic layer comprises a hole blocking layer, and the hole blocking layer comprises any one or more of the heterocyclic compounds described in the present invention.

[0110] Preferably, the organic layer is located outside at least one of the anode and the cathode, and the organic layer includes a covering layer, and the covering layer includes any one or more of the heterocyclic compounds described in the present invention.

[0111] The present invention has no particular limitation on the materials of the thin films in the organic electroluminescent device, and materials known in the art can be used. The organic functional layers of the organic electroluminescent device mentioned above and the electrodes on both sides of the device are introduced below:

[0112] As the anode material of the present invention, a material with a high work function is preferred. The anode can be a transmissive electrode, a reflective electrode or a semi-transmissive electrode. When the anode is a transmissive electrode, the material used to form the anode can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO) or any combination thereof; when the anode is a semi-transmissive electrode or a reflective electrode, the material used to form the anode can be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) or any combination thereof. The anode can have a single-layer structure or a multilayer 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.

[0113] As the hole injection layer material described in the present invention, a material with a high work function is preferred, which can be selected from any one or more of the following structures: metal porphyrins, oligothiophenes, aromatic amine derivatives, perylene derivatives, hexanitrile hexaazatriphenylene compounds, quinacridone compounds, anthraquinone compounds, and polyaniline-based and polythiophene-based conductive polymers, etc., but not limited thereto.

[0114] As the hole transport layer material described in the present invention, a material with high hole mobility is preferred. Specific examples may include carbazole derivatives, triarylamine derivatives, diphenyl diamine derivatives, fluorene derivatives, distilbene derivatives, phthalocyanine compounds, hexanitrile hexaazatriphenylene compounds, quinacridone compounds, anthraquinone compounds, polyaniline, polythiophene, polyvinyl carbazole, etc., but are not limited thereto.

[0115] As the luminescent layer material of the present invention, red, green or blue luminescent materials can be used, which usually contain guest (doped) materials and host materials. The guest material can be a simple fluorescent material or a phosphorescent material, or a combination of fluorescent and phosphorescent materials. The host material of the luminescent layer not only needs to have bipolar charge transfer properties, but also needs an appropriate energy level to effectively transfer the excitation energy to the guest luminescent material. This type of material can include distyryl aryl derivatives, isocyanate derivatives, carbazole derivatives, triarylamine derivatives, anthracene derivatives and pyrene derivatives. The guest material can be selected from any one or more of the following structures: metal complexes (such as iridium complexes, platinum complexes, osmium complexes, rhodium complexes, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives, etc., but is not limited thereto.

[0116] As the electron transport layer material described in the present invention, a material with high electron mobility is preferred. In addition to the heterocyclic ring provided by the present invention, any one or more of the following structures can also be selected: metal chelates, oxazolidinone derivatives, thiazole derivatives, diazole derivatives, azobenzene derivatives, diazaanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, quinoline derivatives, phenanthroline derivatives, benzimidazole derivatives, etc., but not limited to these.

[0117] As the hole blocking layer material described in the present invention, it is preferred that the material has a lower energy level, a wider band gap, and a hole blocking ability. In addition to using the heterocyclic compound provided by the present invention, any one or more of the following structures can also be selected: phenanthroline derivatives, rare earth derivatives, oxazole derivatives, triazole derivatives, triazine derivatives, etc., but not limited thereto.

[0118] As the electron injection layer material of the present invention, a material with a low work function is preferred, and specific examples may include: metals, alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, metal complexes, and other substances with high electron injection properties. Examples include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, 8-hydroxyquinoline cesium, tris (8-hydroxyquinoline) aluminum, etc., but are not limited thereto.

[0119] As the cathode material of the present invention, a material with a low work function is preferred, and the cathode can be selected from a transmissive electrode, a semi-reflective electrode or a reflective electrode. When the cathode is a transmissive electrode, the material for forming the cathode can be selected from transparent metal oxides (e.g., ITO, IZO, etc.); when the cathode is a semi-reflective electrode or a reflective electrode, the material for forming the cathode can be selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds thereof or mixtures thereof (e.g., a mixture of Ag and Mg), but not limited thereto.

[0120] The present invention also provides a method for preparing a compound of formula I, but the preparation method of the present invention is not limited thereto. The core structure of the compound of formula I can be prepared by the reaction route shown below, the substituents can be bonded by methods known in the art, and the type and position of the substituents or the number of substituents can be changed according to techniques known in the art.

[0121] [Synthetic route of the compound of formula I]

[0122]

[0123] The Xa, Xb, Xc and Xd are independently selected from any one of I, Br and Cl.

[0124] Description of raw materials, reagents and characterization equipment:

[0125] The present invention has no particular limitation on the sources of the raw materials and reagents used in the following examples. The raw materials and reagents may be commercially available products or prepared by methods well known to those skilled in the art.

[0126] Mass spectrometry was performed using a British Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent;

[0127] The elemental analysis used the Vario EL cube organic element analyzer from Elementar, Germany, with a sample mass of 5 to 10 mg;

[0128] Synthesis Example 1: Preparation of Compound 1

[0129]

[0130] Preparation of intermediate c-1:

[0131] Add raw material d-1 (21.92 g, 100 mmol) to the reaction bottle, add DMF solution (100 mL) to dissolve it, then add CBr4 (36.5 g, 110 mmol) and sodium tert-butoxide (38.4 g, 400 mmol), stir the mixture at room temperature for 30 minutes, after the reaction is completed, pour the solution into distilled water, then extract with dichloromethane, wash the organic phase with distilled water, dry with anhydrous MgSO4, filter and concentrate under reduced pressure. The crude product is purified by flash chromatography (petroleum ether: ethyl acetate = 30: 1) to obtain intermediate c-1 (26.83 g, 90%). HPLC purity ≥ 99.77%. Mass spectrum m / z: 296.9760 (theoretical value: 296.9789).

[0132] Preparation of compound 1:

[0133] (1) Preparation of intermediate A-1:

[0134] Under nitrogen protection, raw material a-1 (24.59 g, 90.00 mmol), biboric acid pinacol ester (22.85 g, 90.00 mmol), Pd(PPh3)4 (1.29 g, 1.12 mmol), K2CO3 (18.66 g, 135.00 mmol), DMF (550 mL) were added to the reaction bottle in sequence, and then heated for 2 hours. After the reaction was completed, it was cooled to room temperature, distilled water was added thereto, and then extracted with ethyl acetate, the organic layer was dried with anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and then recrystallized with toluene: ethanol = 5:1, and dried to obtain intermediate A-1 (24.50 g, yield 85%), HPLC purity ≥ 99.57%. Mass spectrum m / z: 320.1933 (theoretical value: 320.1948).

[0135] (2) Preparation of intermediate B-1:

[0136] Under nitrogen protection, intermediate A-1 (21.14 g, 66.00 mmol), raw material b-1 (12.64 g, 66.00 mmol), Pd(PPh3)4 (0.76 g, 0.66 mmol), K2CO3 (13.68 g, 99.00 mmol) and 350 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to the reaction bottle in sequence, and the mixture was stirred. The above system was heated to reflux for 3.5 hours. After the reaction was completed, it was cooled to room temperature, filtered to obtain a filter cake, and the filter cake was rinsed with ethanol. Finally, the filter cake was recrystallized with toluene: ethanol = 10:1 to obtain intermediate B-1 (16.70 g, yield 83%), HPLC purity ≥ 99.77%. Mass spectrum m / z: 304.1028 (theoretical value: 304.1019).

[0137] (3) Preparation of intermediate C-1:

[0138] Under nitrogen protection, intermediate B-1 (12.80 g, 42.00 mmol), biboric acid pinacol ester (10.67 g, 42.00 mmol), Pd(dppf)Cl2 (0.31 g, 0.42 mmol), KOAc (6.18 g, 63.00 mmol), 1,4-dioxane (150 mL) were added to the reaction bottle in sequence, and then heated to reflux temperature for 4 hours. After the reaction, it was cooled to room temperature, distilled water was added, and then extracted with ethyl acetate, the organic layer was dried with anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and then recrystallized with toluene: ethanol = 20:1, and dried to obtain intermediate C-1 (13.32 g, yield 80%), HPLC purity ≥ 99.85%. Mass spectrum m / z: 396.2274 (theoretical value: 396.2261).

[0139] (4) Preparation of Compound 1:

[0140] Under nitrogen protection, intermediate C-1 (11.10 g, 28.00 mmol), intermediate c-1 (8.35 g, 28.00 mmol), K2CO3 (6.19 g, 44.80 mmol) and 220 mL toluene solvent were added to the reaction bottle in sequence. After nitrogen replaced the air twice, Pd2(dba)3 (0.31 g, 0.34 mmol) and P(t-Bu)3 (0.23 g, 1.13 mmol) were added thereto. The mixture was stirred. After nitrogen replaced the air once, the above-mentioned reactant system was heated to reflux for 5 hours. After the reaction was completed, it was cooled to room temperature, filtered to obtain a filter cake, and the filter cake was rinsed with a small amount of toluene. Finally, the filter cake was recrystallized from toluene to obtain compound 1 (10.65 g, yield 78%), HPLC purity ≥ 99.90%. Mass spectrum m / z: 487.1947 (theoretical value: 487.1936). Theoretical element content (%) C 36 H 25 NO: C, 88.68; H, 5.17; N, 2.87. Measured element content (%): C, 88.64; H, 5.19; N, 2.86.

[0141] Synthesis Example 2: Preparation of Compound 18

[0142]

[0143] According to the method of Example 1, the raw material d-1 was replaced by an equal molar amount of d-18, the raw material a-1 was replaced by an equal molar amount of a-18, the raw material b-1 was replaced by an equal molar amount of b-18, and the intermediate c-1 was replaced by an equal molar amount of c-18 to obtain compound 18 (12.15 g). The solid purity was ≥99.91% by HPLC. Mass spectrum m / z: 570.2677 (theoretical value: 570.2689). Theoretical element content (%) C 42 H 22 D7NO: C, 88.39; H, 6.36; N, 2.45. Measured element content (%): C, 88.42; H, 6.32; N, 2.43.

[0144] Synthesis Example 3: Preparation of Compound 37

[0145]

[0146] Preparation of intermediate b-37:

[0147] (1) Preparation of intermediate E-37:

[0148] Under nitrogen protection, f-37 (18.77 g, 96.00 mmol), biboronic acid pinacol ester (24.38 g, 96.00 mmol), Pd (dppf) Cl2 (0.70 g, 0.96 mmol), KOAc (14.13 g, 144.00 mmol), 1,4-dioxane (350 mL) were added to the reaction bottle in sequence, and the reaction was heated for 2.5 hours. After the reaction was completed, distilled water was added, extracted with dichloromethane, separated, and the organic phase was washed with distilled water three times, dried over anhydrous magnesium sulfate, concentrated by rotary evaporation, cooled and crystallized, and filtered. The obtained solid was recrystallized with toluene: ethanol = 20:5 to obtain intermediate E-37 (20.26 g, yield 87%); HPLC purity 99.61%. Mass spectrum m / z: 242.1167 (theoretical value: 242.1183).

[0149] (2) Preparation of intermediate b-37:

[0150] Under nitrogen protection, the intermediate E-37 (19.40 g, 80.00 mmol), raw material g-37 (26.64 g, 80.00 mmol), Pd (PPh3) 4 (0.92 g, 0.80 mmol), K2CO3 (16.58 g, 120.00 mmol) were added to the reaction bottle in sequence, and 300 mL of toluene / ethanol / water (2:1:1) mixed solvent was added, and the mixture was stirred. The above reactant system was heated to reflux for 3 hours. After the reaction was completed, it was cooled to room temperature, toluene was added and each phase was separated, and the toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. The temperature was lowered for crystallization, and the solid was filtered by suction. The obtained solid was recrystallized with toluene to obtain the intermediate b-37 (22.13 g, yield 86%). HPLC purity 99.64%. Mass spectrum m / z: 319.9895 (theoretical value: 319.9905).

[0151] (4) Preparation of compound 37:

[0152] According to the method of Example 1, the raw material d-1 was replaced with an equal molar amount of d-37, the raw material a-1 was replaced with an equal molar amount of a-37, the raw material b-1 was replaced with an equal molar amount of b-37, and the intermediate c-1 was replaced with an equal molar amount of c-37 to obtain compound 37 (14.81 g). The solid purity was ≥99.96% by HPLC. Mass spectrum m / z: 744.3069 (theoretical value: 744.3079). Theoretical element content (%) C 55 H 32 D4N2O: C, 88.68; H, 5.41; N, 3.76. Measured element content (%): C, 88.64; H, 5.43; N, 3.77.

[0153] Synthesis Example 4: Preparation of Compound 38

[0154]

[0155] According to the method of Example 1, the raw material a-1 was replaced by an equal mole of a-38, and the raw material b-1 was replaced by an equal mole of b-38 to obtain compound 38 (12.90 g). The solid purity was ≥ 99.95% as determined by HPLC. Mass spectrum m / z: 639.2553 (theoretical value: 639.2562). Theoretical element content (%) C 48 H 33 NO: C, 90.11; H, 5.20; N, 2.19. Measured element content (%): C, 90.15; H, 5.18; N, 2.16.

[0156] Synthesis Example 5: Preparation of Compound 43

[0157]

[0158] Preparation of intermediate b-43:

[0159] According to the method of Example 3, the raw material f-37 was replaced by an equal mole of f-43, and the raw material g-37 was replaced by an equal mole of g-43 to obtain intermediate b-43 (18.83 g), and the solid purity was ≥99.83% by HPLC. Mass spectrum m / z: 267.9420 (theoretical value: 267.9403).

[0160] Preparation of compound 43:

[0161] According to the method of Example 1, the raw material a-1 was replaced by an equal molar amount of a-43, the intermediate b-1 was replaced by an equal molar amount of b-43, and the intermediate c-1 was replaced by an equal molar amount of c-43 to obtain compound 43 (12.20 g). The solid purity was ≥ 99.90% by HPLC. Mass spectrum m / z: 565.2168 (theoretical value: 565.2154). Theoretical element content (%) C 40 H 27 N3O: C, 84.93; H, 4.81; N, 7.43. Measured element content (%): C, 84.88; H, 4.83; N, 7.45.

[0162] Synthesis Example 6: Preparation of Compound 52

[0163]

[0164] According to the method of Example 1, intermediate c-1 was replaced with an equal molar amount of c-52 to obtain compound 52 (10.32 g). The solid purity was ≥ 99.88% as determined by HPLC. Mass spectrum m / z: 487.1917 (theoretical value: 487.1936). Theoretical element content (%) C 36 H 25 NO: C, 88.68; H, 5.17; N, 2.87. Measured element content (%): C, 88.69; H, 5.14; N, 2.83.

[0165] Synthesis Example 7: Preparation of Compound 77

[0166]

[0167] According to the method of Example 1, the raw material a-1 was replaced by an equal mole of a-77, and the raw material b-1 was replaced by an equal mole of b-77 to obtain compound 77 (14.06 g). The solid purity was ≥ 99.94% as determined by HPLC. Mass spectrum m / z: 687.2549 (theoretical value: 687.2562). Theoretical element content (%) C 52 H 33 NO: C, 90.80; H, 4.84; N, 2.04. Measured element content (%): C, 90.83; H, 4.80; N, 2.06.

[0168] Synthesis Example 8: Preparation of Compound 143

[0169]

[0170] Preparation of intermediate b-143:

[0171] According to the method of Example 3, the raw material f-37 was replaced with an equal molar amount of f-143 to obtain the intermediate b-143 (21.41 g), and the solid purity was ≥99.85% by HPLC. Mass spectrum m / z: 316.9592 (theoretical value: 316.9607).

[0172] Preparation of compound 143:

[0173] According to the method of Example 1, the raw material a-1 was replaced by an equal molar amount of a-143, the intermediate b-1 was replaced by an equal molar amount of b-143, and the intermediate c-1 was replaced by an equal molar amount of c-52 to obtain compound 143 (15.68 g). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 788.2837 (theoretical value: 788.2828). Theoretical element content (%) C 59 H 36N2O: C, 89.82; H, 4.60; N, 3.55. Measured element content (%): C, 89.86; H, 4.58; N, 3.52.

[0174] Synthesis Example 9: Preparation of Compound 166

[0175]

[0176] According to the method of Example 1, the raw material a-1 was replaced by an equal mole of a-166, the raw material b-1 was replaced by an equal mole of b-166, and the intermediate c-1 was replaced by an equal mole of c-52 to obtain compound 166 (12.80 g). The solid purity was ≥99.92% detected by HPLC. Mass spectrum m / z: 609.2085 (theoretical value: 609.2093). Theoretical element content (%) C 46 H 27 NO: C, 90.62; H, 4.46; N, 2.30. Measured element content (%): C, 90.66; H, 4.43; N, 2.32.

[0177] Synthesis Example 10: Preparation of Compound 192

[0178]

[0179] Preparation of intermediate b-192:

[0180] According to the method of Example 3, the raw material g-37 was replaced with an equal molar amount of g-192 to obtain intermediate b-192 (20.58 g), and the solid purity was ≥99.81% by HPLC. Mass spectrum m / z: 319.9929 (theoretical value: 319.9905).

[0181] Preparation of compound 192:

[0182] According to the method of Example 1, the raw material a-1 was replaced by an equal molar amount of a-192, the intermediate b-1 was replaced by an equal molar amount of b-192, and the intermediate c-1 was replaced by an equal molar amount of c-192 to obtain compound 192 (16.46 g). The solid purity was ≥ 99.98% as determined by HPLC. Mass spectrum m / z: 851.4049 (theoretical value: 851.4065). Theoretical element content (%) C 64 H 45 D4NO: C, 90.21; H, 6.27; N, 1.64. Measured element content (%): C, 90.25; H, 6.26; N, 1.62.

[0183] Synthesis Example 11: Preparation of Compound 237

[0184]

[0185] According to the method of Example 1, the raw material a-1 was replaced by an equal molar amount of a-237, the raw material b-1 was replaced by an equal molar amount of f-143, and the intermediate c-1 was replaced by an equal molar amount of c-192 to obtain compound 237 (13.04 g). The solid purity was ≥ 99.92% as determined by HPLC. Mass spectrum m / z: 612.2214 (theoretical value: 612.2202). Theoretical element content (%) C 45 H 28 N2O: C, 88.21; H, 4.61; N, 4.57. Measured element content (%): C, 88.24; H, 4.57; N, 4.59.

[0186] Synthesis Example 12: Preparation of Compound 250

[0187]

[0188] Preparation of intermediate b-250:

[0189] According to the method of Example 3, the raw material f-37 was replaced by an equal mole of b-166, and the raw material g-37 was replaced by an equal mole of g-250 to obtain the intermediate b-250 (19.12 g), and the solid purity was ≥99.93% by HPLC. Mass spectrum m / z: 269.9737 (theoretical value: 269.9749).

[0190] Preparation of compound 250:

[0191] According to the method of Example 1, the raw material a-1 was replaced by an equal molar amount of a-250, the intermediate b-1 was replaced by an equal molar amount of b-250, and the intermediate c-1 was replaced by an equal molar amount of c-250 to obtain compound 250 (13.98 g). The solid purity was ≥ 99.94% by HPLC. Mass spectrum m / z: 683.3142 (theoretical value: 683.3126). Theoretical element content (%) C 51 H 33 D4NO: C, 89.57; H, 6.04; N, 2.05. Measured element content (%): C, 89.62; H, 6.01; N, 2.04.

[0192] Synthesis Example 13: Preparation of Compound 262

[0193]

[0194] According to the method of Example 1, the raw material d-1 was replaced with an equal molar amount of d-262, the raw material a-1 was replaced with an equal molar amount of a-262, the raw material b-1 was replaced with an equal molar amount of b-262, and the intermediate c-1 was replaced with an equal molar amount of c-262 to obtain compound 262 (13.02 g). The solid purity was ≥99.92% by HPLC. Mass spectrum m / z: 619.2866 (theoretical value: 619.2875). Theoretical element content (%) C 46 H 37 NO: C, 89.14; H, 6.02; N, 2.26. Measured element content (%): C, 89.17; H, 5.98; N, 2.24.

[0195] Synthesis Example 14: Preparation of Compound 265

[0196]

[0197] According to the method of Example 1, the raw material a-1 was replaced by an equal molar amount of a-265, the raw material b-1 was replaced by an equal molar amount of b-265, and the intermediate c-1 was replaced by an equal molar amount of c-192 to obtain compound 265 (15.43 g). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 775.2528 (theoretical value: 775.2511). Theoretical element content (%) C 58 H 33 NO2: C, 89.78; H, 4.29; N, 1.81. Measured element content (%): C, 89.74; H, 4.31; N, 1.79.

[0198] Synthesis Example 15: Preparation of Compound 266

[0199]

[0200] According to the method of Example 1, the raw material a-1 was replaced by an equal mole of a-266, and the raw material b-1 was replaced by an equal mole of b-266 to obtain compound 266 (15.25 g). The solid purity was ≥ 99.97% as determined by HPLC. Mass spectrum m / z: 775.2679 (theoretical value: 777.2668). Theoretical element content (%) C 58 H 35 NO2: C, 89.55; H, 4.54; N, 1.80. Measured element content (%): C, 89.50; H, 4.56; N, 1.79.

[0201] Synthesis Example 16: Preparation of Compound 304

[0202]

[0203] Preparation of intermediate b-304:

[0204] According to the method of Example 3, the raw material f-37 was replaced by an equal mole of f-304, and the raw material g-37 was replaced by an equal mole of g-304 to obtain intermediate b-304 (18.11 g), and the solid purity was ≥99.88% by HPLC. Mass spectrum m / z: 267.9415 (theoretical value: 267.9403).

[0205] Preparation of compound 304:

[0206] According to the method of Example 1, the raw material a-1 was replaced with an equal molar amount of a-304, the intermediate b-1 was replaced with an equal molar amount of b-304, the intermediate c-1 was replaced with an equal molar amount of c-304, and the raw material d-1 was replaced with an equal molar amount of d-304 to obtain compound 304 (14.71 g). The solid purity was ≥99.95% by HPLC. Mass spectrum m / z: 729.2794 (theoretical value: 729.2780). Theoretical element content (%) C 53 H 35 N3O: C, 87.22; H, 4.83; N, 5.76. Measured element content (%): C, 87.24; H, 4.79; N, 5.77.

[0207] Synthesis Example 17: Preparation of Compound 311

[0208]

[0209] Preparation of intermediate b-311:

[0210] According to the method of Example 3, the raw material f-37 was replaced by an equal mole of f-304, and the raw material g-37 was replaced by an equal mole of g-311 to obtain intermediate b-311 (22.46 g), and the solid purity was ≥99.82% by HPLC. Mass spectrum m / z: 320.9901 (theoretical value: 320.9920).

[0211] Preparation of compound 311:

[0212] According to the method of Example 1, the raw material a-1 was replaced by an equal molar amount of a-311, the intermediate b-1 was replaced by an equal molar amount of b-311, the intermediate c-1 was replaced by an equal molar amount of c-311, and the raw material d-1 was replaced by an equal molar amount of d-311 to obtain compound 311 (15.05 g). The solid purity was ≥99.96% detected by HPLC. Mass spectrum m / z: 756.2766 (theoretical value: 756.2777). Theoretical element content (%) C 55 H 36N2O2: C, 87.28; H, 4.79; N, 3.70. Measured element content (%): C, 87.24; H, 4.78; N, 3.73.

[0213] Synthesis Example 18: Preparation of Compound 313

[0214]

[0215] Preparation of intermediate b-313:

[0216] According to the method of Example 3, the raw material f-37 was replaced by an equal mole of f-313, and the raw material g-37 was replaced by an equal mole of g-43 to obtain the intermediate b-313 (21.87 g), and the solid purity was ≥99.86% by HPLC. Mass spectrum m / z: 319.9985 (theoretical value: 319.9967).

[0217] Preparation of compound 313:

[0218] According to the method of Example 1, the raw material a-1 was replaced by an equal molar amount of a-313, the intermediate b-1 was replaced by an equal molar amount of b-313, and the intermediate c-1 was replaced by an equal molar amount of c-52 to obtain compound 313 (15.13 g). The solid purity was ≥ 99.97% as determined by HPLC. Mass spectrum m / z: 771.2607 (theoretical value: 771.2596). Theoretical element content (%) C 56 H 37 NOS: C, 87.13; H, 4.83; N, 1.81. Measured element content (%): C, 87.08; H, 4.85; N, 1.82.

[0219] Synthesis Example 19: Preparation of Compound 347

[0220]

[0221] According to the method of Example 1, the raw material a-1 was replaced by an equal mole of a-347, the raw material b-1 was replaced by an equal mole of b-347, and the intermediate c-1 was replaced by an equal mole of c-347 to obtain compound 347 (13.77 g). The solid purity was ≥ 99.86% as determined by HPLC. Mass spectrum m / z: 655.2069 (theoretical value: 655.2082). Theoretical element content (%) C 46 H 29 N3S: C, 84.25; H, 4.46; N, 6.41. Measured element content (%): C, 84.21; H, 4.45; N, 6.38.

[0222] Synthesis Example 20: Preparation of Compound 382

[0223]

[0224] According to the method of Example 1, the raw material a-1 was replaced by an equal mole of a-382, the raw material b-1 was replaced by an equal mole of b-382, and the intermediate c-1 was replaced by an equal mole of c-347 to obtain compound 382 (15.22 g). The solid purity was ≥ 99.95% as determined by HPLC. Mass spectrum m / z: 754.2452 (theoretical value: 754.2443). Theoretical element content (%) C 55 H 34 N2S: C, 87.50; H, 4.54; N, 3.71. Measured element content (%): C, 87.54; H, 4.52; N, 3.68.

[0225] Synthesis Example 21: Preparation of Compound 419

[0226]

[0227] According to the method of Example 1, the raw material a-1 was replaced by an equal molar amount of a-419, the raw material b-1 was replaced by an equal molar amount of b-382, and the intermediate c-1 was replaced by an equal molar amount of c-419 to obtain compound 419 (15.74 g). The solid purity was ≥ 99.98% as determined by HPLC. Mass spectrum m / z: 802.2430 (theoretical value: 802.2443). Theoretical element content (%) C 59 H 34 N2S: C, 88.25; H, 4.27; N, 3.49. Measured element content (%): C, 88.29; H, 4.25; N, 3.46.

[0228] Synthesis Example 22: Preparation of Compound 438

[0229]

[0230] Preparation of intermediate b-438:

[0231] According to the method of Example 3, the raw material f-37 was replaced by an equal mole of b-1, and the raw material g-37 was replaced by an equal mole of g-250 to obtain the intermediate b-438 (18.90 g), and the solid purity was ≥99.95% by HPLC. Mass spectrum m / z: 269.9763 (theoretical value: 269.9749).

[0232] Preparation of compound 438:

[0233] According to the method of Example 1, the raw material a-1 was replaced by an equal molar amount of a-438, the intermediate b-1 was replaced by an equal molar amount of b-438, and the intermediate c-1 was replaced by an equal molar amount of c-438 to obtain compound 438 (14.02 g). The solid purity was ≥ 99.94% as determined by HPLC. Mass spectrum m / z: 685.2751 (theoretical value: 685.2741). Theoretical element content (%) C 50 H 31 D4NS: C, 87.55; H, 5.73; N, 2, 04. Measured element content (%): C, 87.51; H, 5.71; N, 2.06.

[0234] Synthesis Example 23: Preparation of Compound 468

[0235]

[0236] According to the method of Example 1, the raw material a-1 was replaced by an equal mole of a-468, the raw material b-1 was replaced by an equal mole of b-468, and the intermediate c-1 was replaced by an equal mole of c-347 to obtain compound 468 (16.29 g). The solid purity was ≥ 99.98% as determined by HPLC. Mass spectrum m / z: 842.2744 (theoretical value: 842.2756). Theoretical element content (%) C 62 H 38 N2S: C, 88.33; H, 4.54; N, 3.32. Measured element content (%): C, 88.36; H, 4.50; N, 3.30.

[0237] Example 24: Testing of glass transition temperature

[0238] Test samples: compounds prepared in the synthesis examples of the present invention and comparative compounds 1-2.

[0239] Test instrument: DSC 25 differential scanning calorimeter (TA Company, USA);

[0240] Test conditions: The test atmosphere is nitrogen, the flow rate of nitrogen is 50mL / min; the heating rate is 10℃ / min, and the temperature range is 50~350℃. The test results of glass transition temperature (Tg) are shown in Table 1:

[0241] Table 1:

[0242] Compound Glass transition temperature(℃) Compound Glass transition temperature(℃) Compound 1 115.8 Compound 265 119.3 Compound 18 116.0 Compound 266 118.9 Compound 37 119.5 Compound 304 117.8 Compound 38 116.2 Compound 311 118.8 Compound 43 116.4 Compound 313 118.5 Compound 52 116.1 Compound 347 117.9 Compound 77 116.3 Compound 382 117.0 Compound 143 117.1 Compound 419 118.2 Compound 166 117.3 Compound 438 116.7 Compound 192 117.5 Compound 468 118.0 Compound 237 116.5 Comparative Compound 1 102.5 Compound 250 119.6 Comparative Compound 2 111.7 Compound 262 118.4

[0243] As shown in Table 1, the compound of the present invention has a higher glass transition temperature than comparative compound 1 and comparative compound 2, and the thermal stability and film-forming property of the material are improved. Applying the compound to an organic electroluminescent device can extend the service life of the device.

[0244] [Device Example 1]

[0245] First, the glass substrate with ITO / Ag / ITO vapor-deposited was cleaned twice in distilled water, ultrasonically washed for 30 minutes, and then repeatedly cleaned twice with distilled water, ultrasonically washed for 10 minutes. After the distilled water cleaning, ultrasonically washed with isopropyl alcohol, acetone, and methanol solvents in sequence, and then dried on a hot plate heated to 120°C. The dried substrate was transferred to a plasma cleaning machine and transferred to a vapor deposition machine after washing for 5 minutes.

[0246] Then, a mixture of P-1 and HI-1 (mass ratio HI-1:P-1=97:3) was evaporated on the cleaned ITO / Ag / ITO substrate as a hole injection layer with a deposition thickness of 15 nm, HI-1 was evaporated on the hole injection layer as a hole transport layer with a deposition thickness of 80 nm, and then a mixture of BH-1 and BD-1 (mass ratio BH-1:BD-1=92:8) was vacuum evaporated on the hole transport layer to form a light-emitting layer with a deposition thickness of 42 nm, and the compound of the present invention was evaporated on the light-emitting layer. Material 1 and Liq (doping ratio is 1:1) are used as electron transport layer with a vapor deposition thickness of 30nm, LiF is evaporated on the electron transport layer as electron injection layer with a vapor deposition thickness of 1nm, and then Mg:Ag (mass ratio Mg:Ag=1:9) is evaporated on the electron injection layer as a cathode with a vapor deposition thickness of 13nm, and then CP-1 is vacuum evaporated on the cathode as a covering layer with a vapor deposition thickness of 65nm, thereby preparing an organic electroluminescent device (the material structure of each functional layer in the preparation process of the organic electroluminescent device is as follows).

[0247]

[0248] [Device Examples 2 to 23]

[0249] Compound 18, compound 37, compound 38, compound 43, compound 52, compound 77, compound 143, compound 166, compound 192, compound 237, compound 250, compound 262, compound 265, compound 266, compound 304, compound 311, compound 313, compound 347, compound 382, ​​compound 419, compound 438, and compound 468 of the present invention are used to replace compound 1 in device example 1 as an electron transport layer, and the other preparation steps are the same as those of device example 1 to prepare organic electroluminescent devices 2 to 23.

[0250] [Device Example 24]

[0251] A mixture of P-1 and HI-1 (mass ratio HI-1:P-1=97:3) was evaporated on the cleaned ITO / Ag / ITO substrate as a hole injection layer with a deposition thickness of 15 nm. The compound HI-1 of the present invention was evaporated on the hole injection layer as a hole transport layer with a deposition thickness of 80 nm. Then, a mixture of BH-1 and BD-1 (mass ratio BH-1:BD-1=92:8) was vacuum evaporated on the hole transport layer to form a light-emitting layer with a deposition thickness of 42 nm. The compound 1 of the present invention was evaporated on the light-emitting layer. As a hole blocking layer, the evaporation thickness is 27nm, and then ET-1 and Liq (doping ratio is 1:1) are evaporated on the hole blocking layer as an electron transport layer, and the evaporation thickness is 30nm, and LiF is evaporated on the electron transport layer as an electron injection layer, and the evaporation thickness is 1nm, and then Mg:Ag (mass ratio Mg:Ag=1:9) is evaporated on the electron injection layer as a cathode, and the evaporation thickness is 13nm, and then CP-1 is vacuum evaporated on the cathode as a covering layer, and the evaporation thickness is 65nm, thereby preparing an organic electroluminescent device 24.

[0252] [Device Examples 25 to 46]

[0253] Compound 18, compound 37, compound 38, compound 43, compound 52, compound 77, compound 143, compound 166, compound 192, compound 237, compound 250, compound 262, compound 265, compound 266, compound 304, compound 311, compound 313, compound 347, compound 382, ​​compound 419, compound 438, and compound 468 of the present invention are used to replace compound 1 in device example 24 as a hole blocking layer, and the other preparation steps are the same as those of device example 24 to prepare organic electroluminescent devices 25 to 46.

[0254] [Comparative Device Examples 1-2]

[0255] Comparative compounds 1 and 2 were used to replace compound 1 in device example 1 as the electron transport layer, and other preparation steps were the same as those in device example 1 to prepare comparative devices 1-2.

[0256] [Comparative Device Examples 3 to 4]

[0257] Comparative compounds 1 and 2 were used to replace compound 1 in device example 24 as the hole blocking layer, and the other preparation steps were the same as those in device example 24 to prepare comparative devices 3 to 4.

[0258] The test software, computer, K2400 digital source meter produced by Keithley Company of the United States and PR788 spectrum scanning luminance meter of PhotoResearch Company of the United States are combined into a joint IVL test system to test the driving voltage and luminous efficiency of the organic electroluminescent device. The life test adopts the M6000 OLED life test system of McScience Company. The test environment is the atmospheric environment and the temperature is room temperature. The luminous characteristics test results of the organic electroluminescent devices obtained by devices 1 to 46 in the device embodiment of the present invention and comparative examples 1 to 4 are shown in Table 2 below.

[0259] Table 2:

[0260]

[0261]

[0262] From the results in Table 2, it can be seen that when the heterocyclic compound provided by the present invention is used in the electron transport layer or the hole blocking layer of the organic electroluminescent device, since such compound has a high electron mobility and a high triplet energy level, it can effectively transport electrons and block holes from escaping to the electron transport layer, thereby increasing the recombination probability of electrons and holes in the light-emitting layer, thereby reducing the driving voltage of the organic electroluminescent device, improving the luminous efficiency of the device, and extending the service life of the device.

[0263] [Device Example 47]

[0264] HI-2 was evaporated on the cleaned ITO / Ag / ITO substrate as a hole injection layer with a thickness of 15 nm. HT-2 was evaporated on the hole injection layer as a hole transport layer with a thickness of 120 nm. Then, GH-1 and GH-2 were vacuum evaporated on the hole transport layer as the main materials, and GD-1 was used as the doping material (the mass ratio of the three GH-1:GH-2:GD-1=45:45:10) to form a light-emitting layer with a thickness of 30 nm. ET-2 and Liq (mass ratio 1:1) were evaporated on the light-emitting layer. The method comprises the following steps: a) vacuum-depositing the compound 1 of the present invention on the cathode as a covering layer, and vacuum-depositing the compound 1 of the present invention on the cathode as a covering layer, and the vapor deposition thickness is 70 nm, thereby preparing an organic electroluminescent device (the material structure of each functional layer in the preparation process of the organic electroluminescent device is as follows).

[0265]

[0266] [Device Examples 48 to 56]

[0267] Organic electroluminescent devices 48 to 56 were prepared by using compounds 37, 52, 77, 166, 237, 266, 313, 347 and 419 of the present invention instead of compound 1 in device example 47 as a covering layer, and the other preparation steps were the same as those of device example 47.

[0268] [Comparative Example 5]

[0269] Comparative device 5 was prepared by using comparative compound 3 instead of compound 1 in device example 47 as the covering layer and the other preparation steps were the same as those of device example 47.

[0270] The test software, computer, K2400 digital source meter produced by Keithley Company of the United States and PR788 spectrum scanning luminance meter of PhotoResearch Company of the United States are combined into a joint IVL test system to test the luminous efficiency of organic electroluminescent devices. The life test adopts the M6000 OLED life test system of McScience Company. The test environment is the atmospheric environment and the temperature is room temperature. The luminous characteristics test results of the organic electroluminescent devices obtained by devices 48 to 56 in the device embodiment of the present invention and comparative example 5 are shown in Table 3 below.

[0271] Table 3:

[0272]

[0273]

[0274] According to the results in Table 3, the heterocyclic compound provided by the present invention has a higher refractive index and a higher glass transition temperature. When applied to the covering layer of an organic electroluminescent device, the light extraction efficiency of the organic electroluminescent device can be effectively improved, thereby improving the luminous efficiency of the device and extending the service life of the device.

[0275] It should be noted that the present invention is particularly described using individual implementation schemes. For ordinary technicians in the technical field, several improvements and modifications can be made to the present invention without departing from the principles of the present invention. These improvements and modifications also fall within the scope of protection of the present invention.

Claims

1. A compound containing a heterocycle, characterized in that The heterocyclic compound has a structure as shown in Formula I: In formula I, E is selected from any one of the following groups: The R5 is independently selected from any one of hydrogen and deuterium; The R 5a Independently selected from any one of hydrogen, deuterium, deuterium-substituted or unsubstituted phenyl; The m1 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, and the m2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; * indicates fusion site; The A is independently selected from any one of the following groups: The R3 is independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, pyridyl, any one of the following groups substituted by deuterium: phenyl, pyridyl; The R6 is independently selected from any one of hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl; wherein a0 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, wherein a1 is independently selected from 0, 1, 2, 3 or 4, wherein a3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, wherein a4 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, wherein a5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; wherein a6 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14, wherein a8 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7, wherein a 10 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said a 12 Independently selected from 0, 1, 2, 3, 4 or 5 The L is independently selected from any one of the following substituted or unsubstituted groups: The "substituted" group is selected from deuterium; The Y is selected from any one of O and S.

2. A compound containing a heterocycle according to claim 1, characterized in that Said Any one selected from the following groups: The R5 is independently selected from any one of hydrogen and deuterium; The m1 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, and the m2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

3. A compound containing a heterocycle according to claim 1, characterized in that: The A is independently selected from any one of the following groups: The R3 is independently selected from any one of hydrogen and deuterium; The R6 is independently selected from any one of hydrogen and deuterium.

4. A compound containing a heterocycle according to claim 1, characterized in that: The L is independently selected from any one of the following substituted or unsubstituted groups: The "substituted" groups are selected from deuterium.

5. A compound containing a heterocycle, characterized in that The heterocyclic compound is selected from any one of the following structures:

6. An organic electroluminescent device, comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside at least one of the anode and the cathode, characterized in that: The organic layer contains any one or more of the heterocyclic ring-containing compounds according to any one of claims 1 to 5.

7. An organic electroluminescent device according to claim 6, characterized in that: The organic layer comprises at least one of an electron transport layer and a hole blocking layer, and the at least one of the electron transport layer and the hole blocking layer comprises any one or more of the heterocyclic compound according to any one of claims 1 to 5.

8. The organic electroluminescent device according to claim 6, characterized in that: The organic layer includes a cover layer, and the cover layer includes any one or more of the heterocyclic ring-containing compounds according to any one of claims 1 to 5.

Images