Heterocyclic compound and organic electroluminescent device thereof

Abstract

The invention provides a heterocyclic compound and an organic electroluminescent device thereof, and relates to the field of organic electroluminescent materials. In order to solve the problems of low luminous efficiency and short service life of the organic electroluminescent device in the prior art, the invention provides the heterocyclic compound with excellent performance and the organic electroluminescent device. The heterocyclic compound provided by the invention has high electron mobility, can improve the electron transport efficiency, and particularly, when the heterocyclic compound is matched with the compound shown in the formula 2 provided by the invention, the carrier transport efficiency can reach balance, the recombination probability of holes and electrons in a luminous layer is greatly improved, and the luminous efficiency of the organic electroluminescent device is further improved; meanwhile, the compounds in the formula 1 and the formula 2 provided by the invention have relatively high Tg, are good in stability during evaporation film forming, and can prolong the service life of a device.

Description

Technical Field

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

[0002] Organic electroluminescent (OLED) display technology has gradually become a hot topic in the research of the new generation of flat-panel displays due to its many advantages, such as full solid-state, high luminous efficiency, high color contrast, fast response speed, no viewing angle limitation, light texture, low power consumption, and easy implementation of flexible display and 3D display.

[0003] The luminescence principle of organic electroluminescent devices is that under the action of an external electric field, holes and electrons are injected from the anode and cathode respectively, and then recombine in the light-emitting layer to form excitons. The excitons transfer energy to the organic light-emitting molecules, causing them to transition from the ground state to the excited state. The excited state molecules are in an unstable state. When the excited molecules return to the ground state from the excited state, the energy is released in the form of light, resulting in luminescence. Currently, the device structure of OLEDs is mostly sandwich-shaped, including a cathode, an anode, and an organic layer placed between the two. The organic layers are also divided into hole injection layer, hole transport layer, luminescence auxiliary layer, hole blocking layer, electron injection layer, electron transport layer, light-emitting layer, and light efficiency improvement layer according to their respective functions.

[0004] Currently, organic electroluminescent devices (OLEDs) exhibit low luminous efficiency and short lifespans. This is due to the low electron transport efficiency of electron transport materials, as well as the much higher hole mobility than electron mobility. This leads to unbalanced carrier transport, making it difficult for electrons and holes to recombine effectively in the luminescent layer. Some electrons and holes escape from the luminescent layer, resulting in reduced luminous efficiency and increased driving voltage. Therefore, to address the current problems with electron transport materials, further optimization and innovation of these materials is needed. Summary of the Invention

[0005] In order to solve the problems existing in the prior art, the present invention provides a heterocyclic compound and an organic electroluminescent device thereof, which can improve the luminous efficiency of the organic electroluminescent device and extend the service life of the device.

[0006] Specifically, the present invention provides a heterocyclic compound having a structure represented by Formula 1:

[0007]

[0008] In Formula 1, R1 and R2 are independently selected from hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and any one of the following groups:

[0009]

[0010] The R 14 Any one independently selected from hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl;

[0011] The m1 is independently selected from 1, 2, 3 or 4, the m2 is independently selected from 1, 2 or 3, the m3 is independently selected from 1, 2, 3, 4, 5 or 6, and the m4 is independently selected from 1, 2, 3, 4 or 5; or R1 and R2 are connected to form the following ring structure:

[0012]

[0013] R3 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0014] Said n1 is independently selected from 1, 2, 3 or 4,

[0015] Said Z is independently selected from C(R4) or N;

[0016] The ring E is selected from any one of the following groups:

[0017]

[0018] Said V is independently selected from C(R5) or N;

[0019] R4 and R5 are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C12 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0020] The X is independently selected from C(R6) or N; and at least one X is selected from N; the R6 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0021] The L1 is independently selected from any one of the following groups:

[0022]

[0023] The Y is independently selected from C(R7) or N, and the R7 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C3-C12 cycloalkyl; or two adjacent R7s are connected to form any one of a substituted or unsubstituted C3-C7 aliphatic ring or a benzene ring;

[0024] The R0 is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C3-C12 cycloalkyl;

[0025] The Ar1 is independently selected from any one of the following groups:

[0026]

[0027] The Q is independently selected from C(R 10 ) or N, said R 10 Any one independently selected from hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl; or two adjacent R 10 They are connected to form a substituted or unsubstituted C3-C7 aliphatic ring;

[0028] The R8 is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0029] The R9 is selected from any one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C2-C30 heteroaryl group;

[0030] The L2 is independently selected from any one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted pyridylene group, and a substituted or unsubstituted pyrimidylene group;

[0031] The "substituted" group in L2 is selected from any one of deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C3-C12 cycloalkyl;

[0032] Ar2 and Ar3 are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; t is selected from 1 or 2;

[0033] The X0 is independently selected from O, S, C (R 11 R 12 ) or N(R 13 );

[0034] The R 11 、R 12 、R 13 independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0035] Another embodiment of the present invention provides 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, and the organic layer comprises an electron transport region, a light-emitting layer, and a hole transport region, wherein the electron transport region is located between the light-emitting layer and the cathode, and the hole transport region is located between the light-emitting layer and the anode, and the electron transport region comprises any one of the heterocyclic compounds described in the present invention.

[0036] The heterocyclic compound provided by the present invention has high electron mobility and can effectively improve electron transport efficiency. At the same time, the heterocyclic compound also has a deep HOMO energy level, which can effectively block the escape of holes to the electron transport layer side, increase the probability of holes and electrons recombining to form excitons in the light-emitting layer, and reduce the probability of holes and electrons recombining to emit light at the interface of the light-emitting layer, thereby improving the luminous efficiency and life of the organic electroluminescent device. At the same time, this type of heterocyclic compound has a high Tg value and good film-forming stability, avoiding problems such as a sudden drop in device life. In particular, when the heterocyclic compound is combined with the aromatic amine compound of formula 2 provided by the present invention, the combination of the two can promote carrier transport to achieve balance, further improve the luminous efficiency of the organic electroluminescent device, and improve the performance of the device. DETAILED DESCRIPTION

[0037] The present invention is further illustrated below with reference to specific examples. It should be understood that these examples are only used to illustrate the present invention and are not used to limit the scope of the present invention. After reading the present invention, modifications of various equivalent forms of the present invention made by those skilled in the art all fall within the scope of protection claimed in this application.

[0038] In the compounds of the present invention, any atom not designated as a particular isotope encompasses any stable isotope of that atom and includes the atom at both its natural isotopic abundance and unnatural abundance.

[0039] The halogens described in the present invention include fluorine, chlorine, bromine and iodine.

[0040] In the present invention, when the position of a substituent on an aromatic ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the aromatic ring. For example, Can represent Can represent Can represent And so on.

[0041] 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 any of the corresponding optional sites of the rings. For example, Can represent Can represent And so on.

[0042] In the present invention, "two adjacent groups are connected to form a ring" means that the adjacent groups are bonded to each other and optionally aromatized to form a substituted or unsubstituted aromatic ring, heteroaromatic ring, aliphatic ring, or aliphatic heterocycle. The "adjacent groups" refer to two substituents on two directly connected atoms, a substituent that is spatially closest to the corresponding substituent, or another substituent on an atom with a corresponding substituent. For example, two substituents substituted at the ortho position of a benzene ring or two substituents on the same carbon atom in an aliphatic ring can be considered "adjacent" to each other.

[0043] The aliphatic ring and the aliphatic heterocycle may be saturated or unsaturated, and may include cycloalkanes, cycloalkenes, cycloalkynes, etc.; the specific ring formed by the connection may be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, a spiro ring or a condensed ring; the number of carbon atoms in the aromatic ring formed is preferably 6 to 30 carbon atoms, particularly preferably 6 to 18 carbon atoms, more preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms; the number of carbon atoms in the heteroaromatic ring formed is preferably 6 to 30 carbon atoms, particularly preferably 6 to 18 carbon atoms, more preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms; The number of carbon atoms in the aliphatic ring is preferably 2 to 30, particularly preferably 2 to 18, and most preferably 2 to 12. The number of carbon atoms in the aliphatic ring formed is preferably 3 to 30, particularly preferably 3 to 18, more preferably 3 to 12, and most preferably 3 to 7. The number of carbon atoms in the aliphatic heterocyclic ring formed is preferably 2 to 30, particularly preferably 2 to 18, more preferably 2 to 12, and most preferably 2 to 7. Further, the ring formed by the connection may be, for example, benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentaacene, cyclohexene, cyclohexane, cyclohexaacene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0044]

[0045] The term "substituted" in "substituted or unsubstituted" as used herein, such as "substituted or unsubstituted alkyl, substituted or unsubstituted silyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene," means that at least one hydrogen atom in the group is replaced by a substituent. When multiple hydrogen atoms are replaced by multiple substituents, the multiple substituents may be the same or different. The substituents include the following groups: deuterium, tritium, cyano, nitro, hydroxyl, halogen atoms, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, 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 are not limited thereto. The substituents are preferably the following groups: deuterium, tritium, cyano, fluorine, chlorine, bromine, iodine, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, adamantyl, norbornyl, trifluoromethyl, trifluoroethyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, trideuteromethyl, methoxy, ethoxy, phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, anthracenyl, pyrenyl, benzocyclohexenyl, benzocycloheptenyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9'-spirobifluorenyl, diphenylamino, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, Quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, benzoquinolinyl, benzoisoquinolinyl, phenanthrolinyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, imidazolyl, benzimidazolyl, benzothiadiazolyl, benzoxadiazolyl, benzotriazolyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, indolyl, carbazolyl, etc., but are not limited thereto.

[0046] The alkyl group described herein refers to a monovalent group obtained by removing a hydrogen atom from an alkane molecule. It may be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 12 carbon atoms, more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 6 carbon atoms. Examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, and n-hexyl.

[0047] The cycloalkyl group herein refers to a monovalent group obtained by removing a hydrogen atom from a cyclic alkane molecule, preferably having 3 to 12 carbon atoms, more preferably 3 to 10 carbon atoms, and particularly preferably 3 to 7 carbon atoms. Examples include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, and norbornane.

[0048] The aryl group described in the present invention refers to a general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon nucleus of an aromatic compound molecule. The aryl group includes a monocyclic aryl group, a polycyclic aryl group, a condensed ring aryl group or a combination thereof. Preferably, the aryl group has 6 to 30 carbon atoms, particularly preferably 6 to 18 carbon atoms, more preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms. Examples include the following groups, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthrenyl, anthracenyl, triphenylene, pyrenyl, fluoranthenyl, 9,9-dimethylfluorenyl, 9-methyl-9-phenylfluorenyl, benzo 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, benzo 9,9-diphenylfluorenyl, 9,9'-spirobifluorenyl, benzo 9,9'-spirobifluorenyl, etc., but are not limited thereto.

[0049] The heteroaryl group described in the present invention refers to a monovalent group obtained by replacing one or more aromatic carbon atoms in an aromatic hydrocarbon molecule by a heteroatom, wherein the heteroatom includes but is not limited to oxygen, sulfur, nitrogen, silicon or phosphorus atoms, preferably 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, and most preferably 2 to 12 carbon atoms. Examples of the heteroaryl groups include, but are not limited to, oxazolyl, benzoxazolyl, naphthoxazolyl, phenanthroxazolyl, anthroxazolyl, tribenzoxazolylene, pyridoxazolyl, thiazolyl, benzothiazolyl, naphthothiazolyl, phenanthrothiazolyl, anthrothiazolyl, tribenzothiazolylene, pyridothiazolyl, imidazolyl, benzimidazolyl, naphthioimidazolyl, phenanthroimidazolyl, anthroimidazolyl, tribenzimidazolyl, pyridoimidazolyl, oxadiazolyl, benzoxadiazolyl, thiadiazolyl, benzothiadiazolyl, triazolyl, benzotriazolyl, spirofluorenyloxanthryl, spirofluorenylthioanthryl, furyl, benzofuranyl, pyridofuranyl, naphthiofuranyl, phenanthrofuranyl, anthracene thienyl, benzothienyl, pyridothiphenyl, naphthiophenyl, phenanthrothiphenyl, anthrathiophenyl, tribenzothienyl, dibenzothiophenyl, benzodibenzothiophenyl, indolyl, naphthioindolyl, phenanthrothiphenyl, anthraindolyl, tribenzoindolyl, carbazolyl, benzocarbazolyl, pyridyl, pyrimidinyl, bipyrimidinyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, o-phenanthroline, benzoquinolyl, benzoisoquinolyl, benzoquinazoline, benzoquinoxaline, etc., but are not limited thereto.

[0050] The silyl group described in the present invention refers to a monovalent group formed by removing a hydrogen atom from a silane molecule, and can be represented by the group described by *—Si(Rs)(Rs)(Rs), wherein Rs is selected from hydrogen, deuterium, cyano, halogen, or any one or more of the alkyl, alkenyl, alkoxy, cycloalkyl, aryl, and heteroaryl groups as described above, preferably having 1 to 30 carbon atoms, preferably having 1 to 25 carbon atoms, more preferably having 1 to 22 carbon atoms, and most preferably having 1 to 18 carbon atoms. Examples may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, dimethyl-tert-butylsilyl, diethylmethylsilyl, tricyclopropylsilyl, tricyclobutylsilyl, triphenylsilyl, triphenylsilyl, dimethylphenylsilyl, etc., but are not limited thereto.

[0051] The arylene group in the present invention refers to an aryl group having two bonding sites, i.e., a divalent group. Except for being a divalent group, the above description of the aryl group applies.

[0052] The heteroarylene group in the present invention means a heteroaryl group having two binding sites, i.e., a divalent group. The above description of the heteroaryl group applies except that each of them is a divalent group.

[0053] The present invention provides a heterocyclic compound having a structure represented by Formula 1:

[0054]

[0055] In Formula 1, R1 and R2 are independently selected from hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and any one of the following groups:

[0056]

[0057] The R 14 Any one independently selected from hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl;

[0058] The m1 is independently selected from 1, 2, 3 or 4, the m2 is independently selected from 1, 2 or 3, the m3 is independently selected from 1, 2, 3, 4, 5 or 6, and the m4 is independently selected from 1, 2, 3, 4 or 5; or R1 and R2 are connected to form the following ring structure:

[0059]

[0060] R3 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0061] Said n1 is independently selected from 1, 2, 3 or 4,

[0062] Said Z is independently selected from C(R4) or N;

[0063] The ring E is selected from any one of the following groups:

[0064]

[0065] Said V is independently selected from C(R5) or N;

[0066] R4 and R5 are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C12 aryl, and substituted or unsubstituted C2-C30 heteroaryl; the substituted groups in R4 and R5 are selected from any one of deuterium, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C3-C12 cycloalkyl;

[0067] The X is independently selected from C(R6) or N; and at least one X is selected from N; the R6 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0068] The L1 is independently selected from any one of the following groups:

[0069]

[0070] The Y is independently selected from C(R7) or N, and the R7 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C3-C12 cycloalkyl; or two adjacent R7s are connected to form any one of a substituted or unsubstituted C3-C7 aliphatic ring or a benzene ring;

[0071] The R0 is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C3-C12 cycloalkyl;

[0072] The Ar1 is independently selected from any one of the following groups:

[0073]

[0074] The Q is independently selected from C(R 10 ) or N, said R 10Any one independently selected from hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl; or two adjacent R 10 They are connected to form a substituted or unsubstituted C3-C7 aliphatic ring;

[0075] The R8 is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0076] The R9 is selected from any one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C2-C30 heteroaryl group;

[0077] The L2 is independently selected from any one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted pyridylene group, and a substituted or unsubstituted pyrimidylene group;

[0078] The "substituted" group in L2 is selected from any one of deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C3-C12 cycloalkyl;

[0079] Ar2 and Ar3 are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; t is selected from 1 or 2;

[0080] The X0 is independently selected from O, S, C (R 11 R 12 ) or N(R 13 );

[0081] The R 11 、R 12 、R 13independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0082] Preferably, the Independently selected from any one of the following groups:

[0083]

[0084] More preferably, the heterocyclic compound is selected from any one of Formula 1-1 to Formula 1-7:

[0085]

[0086] The definitions of R1, R2, Z, E, R6, L1, R0, and Ar1 are the same as those in Formula 1. Preferably, the Any one selected from the following groups:

[0087]

[0088]

[0089] R1 and R2 are independently selected from hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted any one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, or any one of the following groups:

[0090]

[0091] The R 14 、R 14 'Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl;

[0092] The m1 is independently selected from 1, 2, 3 or 4, the m2 is independently selected from 1, 2 or 3, the m3 is independently selected from 1, 2, 3, 4, 5 or 6, the m4 is independently selected from 1, 2, 3, 4 or 5, the m5 is independently selected from 1, 2, 3, 4, 5, 6 or 7, and the m6 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8;

[0093] R3 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0094] The n1 is independently selected from 1, 2, 3 or 4, the n2 is independently selected from 1, 2 or 3, the n3 is independently selected from 1, 2, 3, 4, 5 or 6, the n4 is independently selected from 1, 2, 3, 4 or 5, and the n5 is independently selected from 1 or 2.

[0095] More preferably, R3, R4, and R5 are independently selected from hydrogen, deuterium, cyano, nitro, halogen, trimethylsilyl, triethylsilyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropane, cyclopentane, cyclohexane, adamantyl, norbornane, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, benzofuranyl, benzothiophenyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, The invention also includes any one of a deuterated tert-butyl group, a deuterated adamantyl group, a deuterated phenyl group, a deuterated biphenyl group, a deuterated pyridyl group, a methyl-substituted phenyl group, a methyl-substituted biphenyl group, a tert-butyl-substituted phenyl group, a tert-butyl-substituted biphenyl group, a trimethylsilyl-substituted phenyl group, a trimethylsilyl-substituted biphenyl group, a cyano-substituted phenyl group, a cyano-substituted biphenyl group, a fluorine-substituted phenyl group, a fluorine-substituted biphenyl group, a trifluoromethyl group, an adamantyl-substituted phenyl group, and an adamantyl-substituted biphenyl group.

[0096] The R 14 、R 14'are independently selected from hydrogen, deuterium, cyano, nitro, halogen, trimethylsilyl, triethylsilyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, benzofuranyl, benzothiophenyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated tert-butyl, Any one of a butyl group, a deuterated adamantyl group, a deuterated phenyl group, a deuterated biphenyl group, a deuterated pyridyl group, a methyl-substituted phenyl group, a methyl-substituted biphenyl group, a tert-butyl-substituted phenyl group, a tert-butyl-substituted biphenyl group, a trimethylsilyl-substituted phenyl group, a trimethylsilyl-substituted biphenyl group, a cyano-substituted phenyl group, a cyano-substituted biphenyl group, a fluorine-substituted phenyl group, a fluorine-substituted biphenyl group, a trifluoromethyl group, an adamantyl-substituted phenyl group, and an adamantyl-substituted biphenyl group.

[0097] Preferably, L1 is independently selected from any one of the following groups:

[0098]

[0099]

[0100] The R7 and R7' are independently selected from hydrogen, deuterium, cyano, nitro, halogen, or any one of the following substituted or unsubstituted groups:

[0101] methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl;

[0102] The a1 is independently selected from 1, 2, 3 or 4, the a2 is independently selected from 1, 2 or 3, the a3 is independently selected from 1 or 2, the a4 is independently selected from 1, 2, 3, 4, 5 or 6, the a5 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8, and the a6 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0103] Preferably, Ar1 is independently selected from any one of the following groups:

[0104]

[0105]

[0106]

[0107]

[0108] The R 10 、R 10 'Independently selected from hydrogen, deuterium, cyano, nitro, halogen, or any one of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornane, Si(R0)3;

[0109] The R 15 independently selected from hydrogen, deuterium, cyano, nitro, halogen, or any one of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornane, Si(R0)3, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, phenyl, biphenyl;

[0110] The R 11 、R 12 independently selected from hydrogen, deuterium, cyano, nitro, halogen, or any one of the following groups which may be substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornane, Si(R0)3, phenyl, biphenyl;

[0111] The R 13 independently selected from hydrogen, deuterium, cyano, nitro, halogen, or any one of the following groups which may be substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornane, Si(R0)3, phenyl, biphenyl, naphthyl;

[0112] Ar3 is independently selected from hydrogen, deuterium, cyano, nitro, halogen, or any one of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornane, Si(R0)3, phenyl, biphenyl, naphthyl;

[0113] The b1 is independently selected from 1, 2, 3, 4 or 5, the b2 is independently selected from 1, 2 or 3, the b3 is independently selected from 1 or 2, the b4 is independently selected from 1, 2, 3 or 4, the b5 is independently selected from 1, 2, 3, 4, 5 or 6, the b6 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8, the b7 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, the b8 is independently selected from 1, 2, 3, 4, 5, 6 or 7, and the b9 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9.

[0114] More preferably, the Ar1 is independently selected from any one of the following groups:

[0115]

[0116]

[0117] The R 10 、R 15 Independently selected from hydrogen, deuterium, cyano, nitro, halogen, or any one of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornane, Si(R0)3.

[0118] Alternatively, the Ar1 is independently selected from any one of the following groups:

[0119]

[0120]

[0121]

[0122] The R 10 、R 15 independently selected from hydrogen, deuterium, cyano, nitro, halogen, or any one of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornane, Si(R0)3;

[0123] The R 11 、R 12 Any one independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, biphenyl, deuterated methyl, deuterated tert-butyl, deuterated phenyl, deuterated biphenyl;

[0124] The R 13Any one independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, biphenyl, naphthyl, deuterated methyl, deuterated tert-butyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl;

[0125] The Ar3 is independently selected from any one of hydrogen, deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornane, phenyl, biphenyl, and naphthyl.

[0126] More preferably, the Ar1 is independently selected from any one of the following groups:

[0127]

[0128] The R 10 Any one independently selected from Si(R0)3;

[0129] The b1 is independently selected from 1, 2, 3, 4 or 5, the b2 is independently selected from 1, 2 or 3, the b3 is independently selected from 1 or 2, and the b4 is independently selected from 1, 2, 3 or 4.

[0130] Preferably, R0 is independently selected from any one of hydrogen, deuterium, unsubstituted or deuterium-substituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, vinyl, propenyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, and norbornane.

[0131] More preferably, the Si(R0)3 or Independently selected from any one of the following groups:

[0132]

[0133]

[0134] Most preferably, the heterocyclic compound is selected from any one of the following structures:

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167] The above lists some specific chemical structures of the heterocyclic compounds represented by Formula 1 of the present invention, but the present invention is not limited to these listed chemical structures. All groups based on the structure shown in Formula 1 and having substituents as defined above should be included.

[0168] The present invention also provides 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 at least one of the anode and the cathode, and the organic layer comprises a heterocyclic compound represented by Formula 1 of the present invention.

[0169] Preferably, the organic electroluminescent device described in the present invention comprises an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode, and the organic layer comprises an electron transport region, a light-emitting layer, and a hole transport region, wherein the electron transport region is located between the light-emitting layer and the cathode, and the hole transport region is located between the light-emitting layer and the anode, and the electron transport region comprises the heterocyclic compound represented by Formula 1 of the present invention.

[0170] More preferably, the electron transport region comprises at least one of an electron transport layer and a hole blocking layer, and at least one of the electron transport layer and the hole blocking layer comprises the heterocyclic compound represented by Formula 1 of the present invention.

[0171] Further preferably, the hole transport region comprises a triarylamine compound represented by Formula 2:

[0172]

[0173] In Formula 2, Ara1, Ara2, Ara3, Ara4, Ara5, and Ara6 are independently selected from any one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C2-C30 heteroaryl groups;

[0174] The La1, La2, La3, La4, La5, and La6 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C2-C30 heteroarylene group;

[0175] The Lb, Lc, and Ld are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C2-C30 heteroarylene group;

[0176] The Ra is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, 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;

[0177] The q is selected from 1, 2 or 3.

[0178] More preferably, the hole transport region includes a hole transport layer, the hole transport layer further includes at least one of a first hole transport layer and a second hole transport layer, and at least one of the first hole transport layer and the second hole transport layer contains the triarylamine compound represented by Formula 2 of the present invention.

[0179] More preferably, the electron transport layer is located between the light-emitting layer and the cathode, and the hole blocking layer is located between the electron transport layer and the light-emitting layer; the first hole transport layer is located between the light-emitting layer and the anode, and the second hole transport layer is located between the first hole transport layer and the light-emitting layer.

[0180] Further preferably, the hole transport layer further includes a third hole transport layer, and the third hole transport layer is located between the first hole transport layer and the second hole transport layer, or between the light-emitting layer and the second hole transport layer, or between the anode and the first hole transport layer.

[0181] Most preferably, the electron transport layer comprises the heterocyclic compound of Formula 1 of the present invention, and the first hole transport layer comprises the triarylamine compound of Formula 2 of the present invention; or the electron transport layer comprises the heterocyclic compound of Formula 1 of the present invention, and the second hole transport layer comprises the triarylamine compound of Formula 2 of the present invention; or the hole blocking layer comprises the heterocyclic compound of Formula 1 of the present invention, and the first hole transport layer comprises the triarylamine compound of Formula 2 of the present invention; or the hole blocking layer comprises the heterocyclic compound of Formula 1 of the present invention, and the second hole transport layer comprises the triarylamine compound of Formula 2 of the present invention.

[0182] Preferably, the formula 2 is selected from any one of the structures represented by formula 2-A to formula 2-C:

[0183]

[0184] The definitions of Ara1, Ara2, Ara3, Ara4, Ara5, Ara6, La1, La2, La3, La4, La5, La6, Lb, Lc, Ld, and Ra are the same as those in Formula 2.

[0185] Preferably, Ara1, Ara2, Ara3, Ara4, Ara5, and Ara6 are independently selected from any one of the following groups:

[0186]

[0187] Said W1 is independently selected from O, S, C(RcRd) or N(Re); said W2 is independently selected from O, S, C(RfRg) or N(Rh); said W3 is independently selected from O, S or N(Ri);

[0188] The Rb and Rb' are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, 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 Rb's are connected to form a substituted or unsubstituted ring;

[0189] The Rc, Rd, Rf, and Rg are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, 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; or Rc and Rd are connected to form a substituted or unsubstituted ring; or Rf and Rg are connected to form a substituted or unsubstituted ring;

[0190] The Re, Rh, and Ri are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, 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;

[0191] The q1 is independently selected from 1, 2, 3, 4 or 5, the q2 is independently selected from 1, 2, 3 or 4, the q3 is independently selected from 1, 2 or 3, the q4 is independently selected from 1 or 2, the q5 is independently selected from 1, 2, 3, 4, 5 or 6, the q6 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8, the q7 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, the q8 is independently selected from 1, 2, 3, 4, 5, 6 or 7, the q9 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9, the q 10 are independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11.

[0192] More preferably, Rb and Rb' are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trifluoromethyl, deuterated methyl, deuterated ethyl, deuterated tert-butyl, deuterated isopropyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated adamantyl, phenyl, biphenyl, naphthyl, deuterated phenyl, and deuterated biphenyl.

[0193] More preferably, La1, La2, La3, La4, La5, La6, Lb, Lc, and Ld are independently selected from a single bond or any one of the following groups:

[0194]

[0195] Rj and Rj' are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, 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;

[0196] The p1 is independently selected from 1, 2, 3 or 4, the P2 is independently selected from 1, 2 or 3, the P3 is independently selected from 1 or 2, the P4 is independently selected from 1, 2, 3, 4, 5 or 6, the P5 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8, and the P6 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0197] Most preferably, the formula 2 is selected from any one of the following structures:

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229] The above lists some specific chemical structures of the aromatic amine compounds represented by Formula 2 of the present invention, but the present invention is not limited to these listed chemical structures. All chemical structures based on the structure shown in Formula 2 and with substituents as defined above should be included.

[0230] The present invention does not particularly limit the materials of the thin films in the organic electroluminescent device, and materials known in the art can be used. The following is an introduction to the organic functional layers of the organic electroluminescent device and the electrodes on both sides of the device:

[0231] The anode of the present invention needs to have a high work function in order to improve the hole injection efficiency. The anode material can be selected from metal oxides, combinations of metals and oxides, metals or alloys thereof. Specific examples include, but are not limited to, indium tin oxide (ITO), indium zinc oxide (IZO), aluminum (Al), titanium (Ti), gold (Au), platinum (Pt), copper (Cu), silver (Ag), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), and the like.

[0232] The cathode of the present invention needs to have a low work function in order to improve electron injection efficiency. The cathode material can be selected from metals or alloys thereof. Specific examples include, but are not limited to, aluminum (Al), silver (Ag), calcium (Ca), indium (In), and magnesium:silver (Mg:Ag).

[0233] The hole injection layer material of the present invention needs to have good hole injection ability and a more suitable HOMO energy level to reduce the interface barrier between the anode and the hole transport layer and improve the hole injection ability. The hole injection layer material can be selected from aromatic amine derivatives, metal oxides, phthalocyanine metal complexes, polycyano conjugated organic compounds, polymers, etc. Specific examples may include 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), copper phthalocyanine (CuPC), 4,4',4"-tris(N,N-2-naphthylphenylamino)triphenylamine (2-TNATA), 4,4',4"-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), etc., but are not limited thereto.

[0234] The hole transport layer material of the present invention needs to have a high hole mobility to facilitate hole injection. The first hole transport layer material and the second hole transport layer material can be selected from aromatic amine derivatives, carbazole derivatives, fluorene derivatives, polymers, etc., preferably at least one aromatic amine compound represented by Formula 2 of the present invention. Specific examples may include N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di(2-naphthyl)-1,1'-biphenyl-4,4'-diamine (β-NPB), N,N,N',N'-tetra-1-naphthyl[1,1'-biphenyl]-4,4'-diamine (α-TNB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), 4,4',4"-tris(carbazol-9-yl)triphenylamine (TCTA), etc., but are not limited thereto.

[0235] The luminescent layer materials described herein typically contain a guest (doping) material and a host material. The guest material can be a pure fluorescent material, a phosphorescent material, or a TADF material, or a combination of fluorescent and phosphorescent materials. The host material of the luminescent layer must possess bipolar charge transport properties and an appropriate energy level to effectively transfer excitation energy to the guest luminescent material.

[0236] The main material of the light-emitting layer can include distyryl aryl derivatives, stilbene derivatives, carbazole derivatives, triarylamine derivatives, triazine derivatives, anthracene derivatives and pyrene derivatives. Specific examples may include 4,4'-bis(9-carbazole)biphenyl (CBP), 4,4'-bis(9-carbazolyl)-2,2'-dimethylbiphenyl (CDBP), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CZSi), 9,9'-(2,6-pyridinediyldi-3,1-phenylene)bis-9H-carbazole (26DCZPPY), 9,9'-diphenyl-9H,9'H-3,3'-biphenyl Carbazole (BCzPh), 9-(5-(3-(9H-carbazol-9-yl)phenyl)pyridin-3-yl)-9H-carbazole (CPPyC), 4,4'-bis(carbazol-9-yl)-2,2'-dimethylbiphenyl (CDBP), 1,3-bis(N-carbazolyl)benzene (MCP), 9,10-di(2-naphthyl)anthracene (ADN), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (TBADN), etc., but are not limited thereto.

[0237] The guest material of the light-emitting layer can be selected from metal complexes (such as iridium complexes, platinum complexes, osmium complexes, rhodium complexes, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives, etc. Specific examples include bis(2-(naphthalene-2-yl)pyridine)(acetylacetonate)iridium (Ir(npy)2acac), bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), tris[2-(3-methyl-2-pyridyl)phenyl]iridium (Ir(3mppy)3), bis(2-benzo[H]quinoline-C2,N')(acetylacetonate)iridium (Ir(bzq)2(acac)), tris(2-(3,5-diphenylpyridyl)phenyl)iridium (Ir(3mppy)3), methylphenyl)quinoline-C2,N')iridium (Ir(dmpq)3), bis(1-phenyl-isoquinoline)(acetylacetonate)iridium (Ir(piq)2(acac)), 2,5,8,11-tetra-tert-butylperylene (TBPe), rubrene, 9-(9-phenylcarbazol-3-yl)-10-(naphthalene-1-yl) (PCAN), 1,4-bis(4-(9H-carbazol-9-yl)phenylvinyl)benzene (BCzSB), etc., but are not limited thereto.

[0238] The hole-blocking layer of the present invention has good electron transport and hole-blocking capabilities, thereby effectively transporting electrons and limiting the escape of holes to the interface of the light-emitting layer. The hole-blocking layer material can be selected from metal complexes, quinoline derivatives, imidazole derivatives, o-phenanthroline derivatives, triazole derivatives, azabenzene derivatives, etc., preferably at least one of the heterocyclic compounds described in Formula 1 of the present invention. Specific examples may include bis(2-methyl-8-hydroxyquinolinolato-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3,3'-[5'-[3-(3-pyridyl)phenyl][1,1':3',1"-terphenyl]-3,3"-diyl]dipyridine (TmPyPB), etc., but are not limited thereto.

[0239] The electron transport material of the present invention needs to have a high electron mobility to facilitate electron injection. The electron transport layer material can be selected from quinoline derivatives, imidazole derivatives, o-phenanthroline derivatives, triazole derivatives, metal chelates, azabenzene derivatives, diazaanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, etc., preferably at least one of the heterocyclic compounds described in Formula 1 of the present invention. Specific examples may include 8-hydroxyquinoline aluminum (Alq3), 2,9-di(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 1,3,5-tris(4-pyridin-3-ylphenyl)benzene (TpPyPB), 1,3,5-tris(4-pyridinylquinolin-2-yl)benzene (TPyQB), 3-(biphenyl-4-yl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), etc., but are not limited thereto.

[0240] The electron injection material of the present invention needs to have good electron injection ability and have a more suitable LUMO energy level so as to reduce the interface barrier between the cathode and the electron transport layer and enhance the electron injection ability. The electron injection layer material can be selected from metals, alkali metals, alkaline earth metals, metal compounds, metal oxides, metal halides, alkaline earth metal compounds, alkaline earth metal oxides, alkaline earth metal halides, alkali metal compounds, alkali metal oxides, alkali metal halides, etc. Specific examples may include lithium (Li), strontium (Sr), ytterbium (Yb), lithium fluoride (LiF), sodium fluoride (NaF), cesium fluoride (CsF), calcium fluoride (CaF2), 8-hydroxyquinoline lithium (Liq), tris (8-hydroxyquinoline) aluminum (Alq3), cesium carbonate (Cs2CO3), rubidium acetate (CH3COORb), lithium oxide (Li2O), barium oxide (BaO), etc., but are not limited thereto.

[0241] The light-efficiency-improving layer of the present invention functions to couple light out, thereby improving light extraction efficiency. The material for the light-efficiency-improving layer may include metal compounds, triarylamine derivatives, benzidine derivatives, carbazole derivatives, and the like. Specific examples include tris(8-hydroxyquinolinolato)aluminum (Alq3), N,N'-di(naphthalene-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (NPD), and 4,4'-bis(9-carbazole)biphenyl (CBP).

[0242] There is no particular limitation on the method for preparing the thin films in the organic electroluminescent device of the present invention, and vacuum evaporation, sputtering, spin coating, spray coating, screen printing, laser transfer, etc. may be used, but are not limited thereto.

[0243] The organic electroluminescent device of the present invention is mainly used in the fields of information display technology and lighting, and is widely used in various information displays, such as mobile phones, tablet computers, flat-screen TVs, smart watches, VR, car systems, digital cameras, wearable devices, etc.

[0244] Synthesis Example

[0245] Description of raw materials and reagents: The present invention has no particular limitations on the raw materials or reagents used in the following synthesis examples, and they can be commercially available products or prepared using preparation methods well known to those skilled in the art.

[0246] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters, UK); Vario ELcube organic element analyzer (Elementar, Germany).

[0247] The present invention also provides a preparation route for the core structure of the compound of Formula 1 and the compound of Formula 2. The substituents can be bonded by methods known in the art, and the type, position and number of the substituents can be changed according to techniques known in the art.

[0248] [Synthetic Route 1]:

[0249]

[0250] The Xa, Xb, and Xc are independently selected from any one of Cl, Br, and I, and the M is independently selected from

[0251] When Ar1 and When the two are identical or when Ar1 and When the two groups are identical to each other, the above groups can be introduced together in one step;

[0252] Alternatively, the order of the above reactions can be altered to introduce the desired groups.

[0253] The main reaction types involved in the compound of formula 1 are Suzuki coupling reaction and Miyaura borylation reaction. The raw materials in the synthesis route provided by the present invention can be commercially available products or can be prepared by preparation methods known in the art.

[0254] When La, Lb, and Lc are all single bonds, the preparation route of the compound of formula 2 is as follows:

[0255] [Synthetic Route 2]

[0256]

[0257] The Xd, Xe, and Xf are independently selected from any one of Cl, Br, and I;

[0258] when When any two or three of the groups are the same, the above groups can be introduced together in one step;

[0259] The main reaction type involved in the compound of formula 2 is the Buchwald reaction. The raw materials in the synthesis route provided by the present invention can be commercially available products or can be prepared by preparation methods known in the art.

[0260] Synthesis Example 1: Synthesis of Compound 8

[0261]

[0262] Preparation of intermediate b-8: Under nitrogen, a-8 (16.34 g, 60.00 mmol), C-137 (11.65 g, 120.00 mmol), K2CO3 (12.44 g, 90.00 mmol), Pd(PPh3)4 (0.92 g, 0.80 mmol), and 600 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred at reflux for 8 hours. After the reaction, the mixture was cooled to room temperature, filtered, and washed with distilled water. The resulting solid was then recrystallized from toluene to obtain intermediate b-8 (17.76 g, 72% yield). The solid purity was ≥99.83% as determined by HPLC. Mass spectrum: m / z: 411.0928 (theoretical value: 411.0920).

[0263] Preparation of Compound 8: Under nitrogen, b-8 (12.33 g, 30.00 mmol), B-137 (10.87 g, 30.00 mmol), K2CO3 (6.22 g, 45.00 mmol), Pd(dppf)Cl2 (0.22 g, 0.30 mmol), and 480 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred and reacted under reflux for 10 hours. After the reaction, the mixture was cooled to room temperature, filtered, and washed with distilled water. The resulting solid was then recrystallized from toluene to obtain Compound 8 (15.39 g, 74% yield); HPLC analysis showed that the solid had a purity of ≥99.92%. Mass spectrum m / z: 692.3033 (theoretical value: 692.3043). Theoretical element content (%): C 47 H 44 N2Si2: C, 81.45; H, 6.40; N, 4.04. Measured element content (%): C, 81.48; H, 6.43; N, 4.05.

[0264] Synthesis Example 2: Synthesis of Compound 53

[0265]

[0266] Compound 53 (16.01 g) was obtained by the same preparation method as in Example 1, except that C-137 and B-137 were replaced by equimolar amounts of C-172 and B-172, respectively. The remaining steps were the same. The purity of the solid was ≥99.90% as determined by HPLC. Mass spectrum m / z: 720.3368 (theoretical value: 720.3356). Theoretical element content (%): C 49 H 48 N2Si2: C, 81.62; H, 6.71; N, 3.88. Measured element content (%): C, 81.58; H, 6.74; N, 3.85.

[0267] Synthesis Example 3: Synthesis of Compound 137

[0268]

[0269] Preparation of intermediate b-137: Under nitrogen protection, a-137 (18.44 g, 100.00 mmol), A-137 (24.81 g, 100.00 mmol), Na2CO3 (15.90 g, 150.00 mmol), Pd(OAC)2 (0.22 g, 1.00 mmol), P(t-Bu)3 (4.00 mL of 0.50 M toluene solution, 2.00 mmol), and 800 mL of toluene / ethanol / water (2:1:1) were added to the reaction flask, and the reaction was stirred under reflux for 9 hours. After the reaction, the mixture was cooled to room temperature, a small amount of distilled water was added, the organic phase was separated, filtered on silica gel, and the solvent was evaporated under reduced pressure. The crude product obtained after filtration was recrystallized from ethyl acetate to obtain intermediate b-137 (22.54 g, yield 64%); HPLC detection of solid purity ≧99.70%. Mass spectrum m / z: 351.0347 (theoretical value: 351.0330).

[0270] Preparation of intermediate c-137: Under nitrogen, a reaction flask was charged with b-137 (21.13 g, 60.00 mmol), B-137 (21.73 g, 60.00 mmol), Na2CO3 (9.54 g, 90.00 mmol), Pd(PPh3)4 (0.69 g, 0.60 mmol), and 800 mL of toluene / ethanol / water (2:1:1). The mixture was stirred at reflux for 10 hours. After completion of the reaction, the mixture was cooled to room temperature, filtered, and washed with distilled water. The resulting solid was recrystallized from toluene to obtain intermediate c-137 (25.49 g, 67% yield). The solid purity was ≥99.84% by HPLC. Mass spectrum: m / z: 633.1990 (theoretical value: 633.1972).

[0271] Preparation of compound 137: Under nitrogen, c-137 (19.03 g, 30.00 mmol), C-137 (5.82 g, 30.00 mmol), K2CO3 (6.22 g, 45.00 mmol), Pd(dppf)Cl2 (0.22 g, 0.30 mmol), and 500 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred and reacted at reflux for 14 hours. After the reaction, the mixture was cooled to room temperature, filtered, and washed with distilled water. The resulting solid was then recrystallized from toluene to obtain compound 137 (16.16 g, 72% yield); the solid purity was ≥99.95% by HPLC. Mass spectrum: m / z: 747.3084 (theoretical value: 747.3070). Theoretical element content (%): C 53 H 41 N3Si: C, 85.10; H, 5.53; N, 5.62. Measured element content (%): C, 85.13; H, 5.51; N, 5.61.

[0272] Synthesis Example 4: Synthesis of Compound 184

[0273]

[0274] Following the same preparation method as in Example 3 for compound 137, A-137 and B-137 were replaced with equal moles of A-184 and B-184, respectively, and the remaining steps were the same to obtain compound 184 (16.76 g). HPLC analysis of the solid showed a purity of ≥99.94%. Mass spectrum m / z: 797.3237 (theoretical value: 797.3226). Theoretical element content (%): C 57 H43N3Si: C, 85.78; H, 5.43; N, 5.27. Measured element content (%): C, 85.75; H, 5.40; N, 5.29.

[0275] Synthesis Example 5: Synthesis of Compound 203

[0276]

[0277] Following the same preparation method as that of Compound 137 in Example 3, A-137 was replaced with an equal molar amount of A-203, and the other steps were the same to obtain Compound 203 (16.21 g). The purity of the solid was ≥99.93% as determined by HPLC. Mass spectrum m / z: 771.3055 (theoretical value: 771.3070). Theoretical element content (%): C 55 H 41N3Si: C, 85.57; H, 5.35; N, 5.44. Measured element content (%): C, 85.54; H, 5.38; N, 5.45.

[0278] Synthesis Example 6: Synthesis of Compound 225

[0279]

[0280] Following the same preparation method as that of Compound 137 in Example 3, replacing A-137 with an equal molar amount of B-137, and following the same other steps, Compound 225 (18.36 g) was obtained. The purity of the solid was ≥99.92% as determined by HPLC. Mass spectrum m / z: 861.3552 (theoretical value: 861.3539). Theoretical element content (%): C 62 H 47 N3Si: C, 86.37; H, 5.50; N, 4.87. Measured element content (%): C, 86.38; H, 5.52; N, 4.84.

[0281] Synthesis Example 7: Synthesis of Compound 267

[0282]

[0283] Compound 267 (15.94 g) was obtained by the same preparation method as in Example 3, except that A-137 and B-137 were replaced with equimolar amounts of B-184 and B-172, respectively. The remaining steps were the same. The purity of the solid was ≥99.93% as determined by HPLC. Mass spectrum: m / z: 737.3221 (theoretical value: 737.3226). Theoretical element content (%): C 52 H 43 N3Si: C, 84.63; H, 5.87; N, 5.69. Measured element content (%): C, 84.66; H, 5.85; N, 5.68.

[0284] Synthesis Example 8: Synthesis of Compound 291

[0285]

[0286] Compound 291 (18.06 g) was obtained by the same preparation method as in Example 3, except that A-137 and B-137 were replaced with equal moles of B-137 and B-291, respectively. HPLC analysis of the solid showed a purity of ≥99.91%. Mass spectrum: m / z: 859.3369 (theoretical value: 859.3383). Theoretical element content (%): C 62 H 45N3Si: C, 86.58; H, 5.27; N, 4.89. Measured element content (%): C, 86.59; H, 5.29; N, 4.86.

[0287] Synthesis Example 9: Synthesis of Compound 322

[0288]

[0289] Following the same preparation method as that of Compound 137 in Synthesis Example 3, replacing A-137 with an equal molar amount of A-322, and following the same other steps, Compound 322 (14.89 g) was obtained. HPLC analysis of the solid showed a purity of ≥99.92%. Mass spectrum m / z: 698.2851 (theoretical value: 698.2866). Theoretical element content (%): C 48 H 38 N4Si: C, 82.49; H, 5.48; N, 8.02. Measured element content (%): C, 82.47; H, 5.46; N, 8.05.

[0290] Synthesis Example 10: Synthesis of Compound 354

[0291]

[0292] Compound 354 (13.44 g) was obtained by the same preparation method as in Example 3, except that A-137 and B-137 were replaced with equal moles of A-354 and B-172, respectively. The remaining steps were the same. The purity of the solid was ≥99.94% as determined by HPLC. Mass spectrum: m / z: 613.2530 (theoretical value: 613.2549). Theoretical element content (%): C 41 H 35 N3OSi: C, 80.23; H, 5.75; N, 6.85. Measured element content (%): C, 80.26; H, 5.74; N, 6.84.

[0293] Synthesis Example 11: Synthesis of Compound 376

[0294]

[0295] Preparation of A-376: Under nitrogen protection, d-376 (32.78 g, 120 mmol), e-376 (30.47 g, 120 mmol), and KOAc (23.55 g, 240 mmol) were added to the reaction flask, and then 600 mL of DMF solution was added. After the air was replaced with nitrogen three times, Pd(dppf)Cl2 (0.88 g, 1.2 mmol) was added and the reaction was stirred for 8 h. After the reaction was completed, the reactant was cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate (600 mL×3 times). The organic phase was separated and dried over anhydrous magnesium sulfate. The obtained solid was purified with n-hexane:ethyl acetate = 9:1 (v / v) to obtain A-376 (35.35 g, yield 92%), HPLC purity ≧99.93%, mass spectrum m / z: 320.1572 (theoretical value: 320.1584).

[0296] Following the same preparation method as in Example 3 for compound 137, A-137 was replaced with an equal molar amount of A-376, and the other steps were the same to obtain compound 376 (15.72 g). The purity of the solid was ≥99.93% as determined by HPLC. Mass spectrum m / z: 737.2848 (theoretical value: 737.2862). Theoretical element content (%): C 51 H 39 N3OSi: C, 83.01; H, 5.33; N, 5.69. Measured element content (%): C, 83.03; H, 5.32; N, 5.67.

[0297] Synthesis Example 12: Synthesis of Compound 389

[0298]

[0299] Compound 389 (16.55 g) was obtained by the same preparation method as in Example 3, except that A-137, B-137, and C-137 were replaced with equal moles of A-389, B-389, and C-389, respectively. The remaining steps were the same. The purity of the solid was ≥99.91% as determined by HPLC. Mass spectrum: m / z: 787.3012 (theoretical value: 787.3019). Theoretical element content (%): C 55 H 41 N3OSi: C, 83.83; H, 5.24; N, 5.33. Measured element content (%): C, 83.85; H, 5.21; N, 5.32.

[0300] Synthesis Example 13: Synthesis of Compound 438

[0301]

[0302] Compound 438 (16.79 g) was obtained by the same preparation method as in Example 3, except that A-137 and B-137 were replaced with equal moles of A-438 and B-438, respectively. The remaining steps were the same. The purity of the solid was ≥99.90% as determined by HPLC. Mass spectrum: m / z: 787.3430 (theoretical value: 787.3416). Theoretical element content (%): C 53 H 49 N3SSi: C, 80.77; H, 6.27; N, 5.33. Measured element content (%): C, 80.74; H, 6.28; N, 5.34.

[0303] Synthesis Example 14: Synthesis of Compound 107

[0304]

[0305] Compound 107 (18.90 g) was prepared by the same method as in Example 1, except that a-8 was replaced with an equal molar amount of a-107. The remaining steps were the same. The purity of the solid was ≥99.93% as determined by HPLC. Mass spectrum: m / z: 843.3733 (theoretical value: 843.3717). Theoretical element content (%): C 60 H 53 NSi2: C, 85.36; H, 6.33; N, 1.66. Measured element content (%): C, 85.34H, 6.37N, 1.62

[0306] Synthesis Example 15: Synthesis of Compound 468

[0307]

[0308] Following the same preparation method as that of Compound 137 in Example 3, replacing A-137 with an equal molar amount of A-468, and following the same other steps, Compound 468 (15.59 g) was obtained. HPLC analysis of the solid showed a purity of ≥99.91%. Mass spectrum m / z: 731.3679 (theoretical value: 731.3696). Theoretical element content (%): C 51 H 49 N3Si: C, 83.68; H, 6.75; N, 5.74. Measured element content (%): C, 83.69; H, 6.73; N, 5.76.

[0309] Synthesis Example 16: Synthesis of Compound 470

[0310]

[0311]

[0312] Preparation of A-470: Following the same preparation method as compound A-376 in Synthesis Example 11, replace d-376 with an equal molar amount of d-470. The remaining steps were the same to obtain A-470 (34.59 g). The purity of the solid was ≥99.94% as determined by HPLC. Mass spectrum: m / z: 320.1932 (theoretical value: 320.1948).

[0313] Following the same preparation method as in Example 3 for compound 137, A-137 was replaced with an equal molar amount of A-470, and the other steps were the same to obtain compound 470 (15.94 g). The purity of the solid was ≥99.92% as determined by HPLC. Mass spectrum m / z: 737.3207 (theoretical value: 737.3226). Theoretical element content (%): C 52 H 43 N3Si: C, 84.63; H, 5.87; N, 5.69. Measured element content (%): C, 84.66; H, 5.84; N, 5.68.

[0314] Synthesis Example 17: Synthesis of Compound 499

[0315]

[0316] Preparation of A-499: Following the same preparation method as compound A-376 in Synthesis Example 11, replace d-376 with an equal molar amount of d-499. The remaining steps were the same to obtain A-499 (34.20 g). The purity of the solid was ≥99.93% as determined by HPLC. Mass spectrum: m / z: 320.1935 (theoretical value: 320.1948).

[0317] Compound 499 (17.34 g) was obtained by the same preparation method as in Example 3, except that A-137 and C-137 were replaced by equimolar amounts of A-499 and C-172, respectively. The remaining steps were the same. The purity of the solid was ≥99.90% as determined by HPLC. Mass spectrum: m / z: 813.3557 (theoretical value: 813.3539). Theoretical element content (%): C 58 H 47 N3Si: C, 85.57; H, 5.82; N, 5.16. Measured element content (%): C, 85.59; H, 5.85; N, 5.14.

[0318] Synthesis Example 18: Synthesis of Compound 524

[0319]

[0320] Compound 524 (12.74 g) was obtained by the same preparation method as in Example 3, except that A-137, B-137, and C-137 were replaced with equal moles of A-524, B-172, and C-389, respectively. The remaining steps were the same. The purity of the solid was ≥99.93% as determined by HPLC. Mass spectrum: m / z: 573.2616 (theoretical value: 573.2600). Theoretical element content (%): C 39 H 35 N3Si: C, 81.63; H, 6.15; N, 7.32. Measured element content (%): C, 81.61; H, 6.17; N, 7.33.

[0321] Synthesis Example 19: Synthesis of Compound 525

[0322]

[0323] Compound 525 (14.04 g) was obtained by the same preparation method as in Example 3, except that A-137, B-137, and C-137 were replaced with equal moles of A-525, B-172, and C-172, respectively. The remaining steps were the same. The purity of the solid was ≥99.92% as determined by HPLC. Mass spectrum: m / z: 649.2933 (theoretical value: 649.2913). Theoretical element content (%): C 45 H 39 N3Si: C, 83.16; H, 6.05; N, 6.47. Measured element content (%): C, 83.18; H, 6.04; N, 6.45.

[0324] Synthesis Example 20: Synthesis of Compound 532

[0325]

[0326] Compound 532 (13.29 g) was obtained by the same preparation method as in Example 3, except that A-137 and B-137 were replaced with equal moles of A-525 and B-532, respectively. The remaining steps were the same. The purity of the solid was ≥99.91% as determined by HPLC. Mass spectrum: m / z: 623.2753 (theoretical value: 623.2757). Theoretical element content (%): C 43 H 37 N3Si: C, 82.78; H, 5.98; N, 6.74. Measured element content (%): C, 82.77; H, 5.95; N, 6.77.

[0327] Synthesis Example 21: Synthesis of Compound 541

[0328]

[0329] Compound 541 (13.74 g) was obtained by the same preparation method as in Example 3, except that A-137 and B-137 were replaced with equal moles of A-525 and B-541, respectively. The remaining steps were the same. The purity of the solid was ≥99.92% as determined by HPLC. Mass spectrum: m / z: 635.2744 (theoretical value: 635.2757). Theoretical element content (%): C 44 H 37 N3Si: C, 83.11; H, 5.87; N, 6.61. Measured element content (%): C, 83.13; H, 5.85; N, 6.62.

[0330] Synthesis Example 22: Synthesis of Compound 554

[0331]

[0332] Compound 554 (13.62 g) was obtained by the same preparation method as in Example 3, except that A-137 and C-137 were replaced by equimolar amounts of A-524 and C-554, respectively. The remaining steps were the same. The purity of the solid was ≥99.94% as determined by HPLC. Mass spectrum m / z: 621.2614 (theoretical value: 621.2600). Theoretical element content (%): C 43 H 35 N3Si: C, 83.05; H, 5.67; N, 6.76. Measured element content (%): C, 83.08; H, 5.66; N, 6.74.

[0333] Synthesis Example 23: Synthesis of Compound 558

[0334]

[0335] Following the same preparation method as compound 137 in Example 3, replacing A-137 with an equal molar amount of A-558, and following the same other steps, compound 558 (14.44 g) was obtained. The purity of the solid was ≥99.93% as determined by HPLC. Mass spectrum m / z: 677.3241 (theoretical value: 677.3226). Theoretical element content (%): C 47 H 43 N3Si: C, 83.27; H, 6.39; N, 6.20. Measured element content (%): C, 83.28; H, 6.37; N, 6.22.

[0336] Synthesis Example 24: Synthesis of Compound 590

[0337]

[0338] Following the same preparation method as that of Compound 137 in Example 3, replacing A-137 with an equal molar amount of A-590, and following the same other steps, Compound 590 (15.29 g) was obtained. The purity of the solid was ≥99.93% as determined by HPLC. Mass spectrum m / z: 697.2932 (theoretical value: 697.2913). Theoretical element content (%): C 49 H 39 N3Si: C, 84.32; H, 5.63; N, 6.02. Measured element content (%): C, 84.34; H, 5.62; N, 6.05.

[0339] Synthesis Example 25: Synthesis of Compound 591

[0340]

[0341] Compound 591 (15.71 g) was obtained by the same preparation method as in Example 3, except that A-137 and B-137 were replaced with equal moles of A-525 and B-591, respectively. HPLC analysis of the solid showed a purity of ≥99.91%. Mass spectrum: m / z: 747.3058 (theoretical value: 747.3070). Theoretical element content (%): C 53 H 41 N3Si: C, 85.10; H, 5.53; N, 5.62. Measured element content (%): C, 85.13; H, 5.52; N, 5.61.

[0342] Synthesis Example 26: Synthesis of Compound 597

[0343]

[0344] Compound 597 (14.76 g) was obtained by the same preparation method as in Example 3, except that A-137 was replaced with an equal molar amount of A-597. The remaining steps were the same. The purity of the solid was ≥99.90% as determined by HPLC. Mass spectrum m / z: 702.3212 (theoretical value: 702.3227). Theoretical element content (%): C 49 H 34 D5N3Si: C, 83.72; H, 6.31; N, 5.98. Measured element content (%): C, 83.74; H, 6.32; N, 5.95.

[0345] Synthesis Example 27: Synthesis of Compound 606

[0346]

[0347] Compound 606 (15.17 g) was obtained by the same preparation method as in Example 3, except that A-137 and B-137 were replaced with equal moles of A-525 and B-606, respectively. The remaining steps were the same. The purity of the solid was ≥99.92% as determined by HPLC. Mass spectrum m / z: 711.3087 (theoretical value: 711.3070). Theoretical element content (%): C 50 H 41 N3Si: C, 84.35; H, 5.80; N, 5.90. Measured element content (%): C, 84.32; H, 5.81; N, 5.93.

[0348] Synthesis Example 28: Synthesis of Compound 615

[0349]

[0350] Preparation of B-615: Following the same preparation method as compound A-376 in Synthesis Example 11, replace d-376 with an equal molar amount of d-615. The remaining steps were the same to obtain B-615 (52.25 g). The purity of the solid was ≥99.90% as determined by HPLC. Mass spectrum: m / z: 500.2870 (theoretical value: 500.2887).

[0351] Following the same preparation method as that of Compound 137 in Example 3, Compound 615 (15.84 g) was obtained by replacing A-137 and B-137 with equal moles of A-525 and B-615, respectively, with the remaining steps remaining the same. The purity of the solid was ≥99.91% as determined by HPLC. Mass spectrum m / z: 753.3545 (theoretical value: 753.3539). Theoretical element content (%): C 53 H 47 N3Si: C, 84.42; H, 6.28; N, 5.57. Measured element content (%): C, 84.44; H, 6.27; N, 5.55.

[0352] Synthesis Example 29: Synthesis of Compound 623

[0353]

[0354] Compound 623 (16.26 g) was obtained by the same preparation method as in Example 3, except that A-137 and B-137 were replaced with equal moles of A-590 and B-623, respectively. The remaining steps were the same. The purity of the solid was ≥99.90% as determined by HPLC. Mass spectrum: m / z: 773.3239 (theoretical value: 773.3226). Theoretical element content (%): C 55 H 43N3Si: C, 85.34; H, 5.60; N, 5.43. Measured element content (%): C, 85.36; H, 5.62; N, 5.40.

[0355] Synthesis Example 30: Synthesis of Compound 642

[0356]

[0357] Compound 642 (15.40 g) was obtained by the same preparation method as in Example 3, except that A-137 and B-137 were replaced with equal moles of A-525 and B-642, respectively. The remaining steps were the same. The purity of the solid was ≥99.92% as determined by HPLC. Mass spectrum: m / z: 722.2880 (theoretical value: 722.2866). Theoretical element content (%): C 50 H 38 N4Si: C, 83.07; H, 5.30; N, 7.75. Measured element content (%): C, 83.04; H, 5.32; N, 7.77.

[0358] Synthesis Example 31: Synthesis of Compound 645

[0359]

[0360] Compound 645 (15.29 g) was obtained by the same preparation method as in Example 3, except that A-137 and C-137 were replaced by equimolar amounts of A-524 and C-172, respectively. The remaining steps were the same. The purity of the solid was ≥99.93% as determined by HPLC. Mass spectrum: m / z: 697.2923 (theoretical value: 697.2913). Theoretical element content (%): C 49 H 39 N3Si: C, 84.32; H, 5.63; N, 6.02. Measured element content (%): C, 84.33; H, 5.60; N, 6.04.

[0361] Synthesis Example 32: Synthesis of Compound 654

[0362]

[0363] Compound 654 (15.62 g) was obtained by the same preparation method as in Example 3, except that A-137 and C-137 were replaced by equimolar amounts of A-654 and C-172, respectively. The remaining steps were the same. The purity of the solid was ≥99.91% as determined by HPLC. Mass spectrum: m / z: 722.2850 (theoretical value: 722.2866). Theoretical element content (%): C 50 H 38N4Si: C, 83.07; H, 5.30; N, 7.75. Measured element content (%): C, 83.05; H, 5.33; N, 7.74.

[0364] Synthesis Example 33: Synthesis of Compound 656

[0365]

[0366] Compound 656 (15.49 g) was obtained by the same preparation method as in Example 3, except that A-137 and C-137 were replaced by equimolar amounts of A-524 and C-389, respectively. The remaining steps were the same. The purity of the solid was ≥99.94% as determined by HPLC. Mass spectrum: m / z: 697.2925 (theoretical value: 697.2913). Theoretical element content (%): C 49 H 39 N3Si: C, 84.32; H, 5.63; N, 6.02. Measured element content (%): C, 84.34; H, 5.62; N, 6.01.

[0367] Synthesis Example 34: Synthesis of Compound 663

[0368]

[0369] Compound 663 (15.46 g) was obtained by the same preparation method as in Example 3, except that A-137, B-137, and C-137 were replaced with equal moles of A-524, B-663, and C-172, respectively. The remaining steps were the same. The purity of the solid was ≥99.92% as determined by HPLC. Mass spectrum: m / z: 725.3243 (theoretical value: 725.3226). Theoretical element content (%): C 51 H 43 N3Si: C, 84.37; H, 5.97; N, 5.79. Measured element content (%): C, 84.39; H, 5.98; N, 5.76.

[0370] Synthesis Example 35: Synthesis of Compound 679

[0371]

[0372] Compound 679 (16.95 g) was obtained by the same preparation method as in Example 3, except that A-137 and C-137 were replaced by equimolar amounts of A-525 and C-172, respectively. The remaining steps were the same. The purity of the solid was ≥99.92% as determined by HPLC. Mass spectrum: m / z: 773.3207 (theoretical value: 773.3226). Theoretical element content (%): C 55 H 43N3Si: C, 85.34; H, 5.60; N, 5.43. Measured element content (%): C, 85.36; H, 5.62; N, 5.40.

[0373] Synthesis Example 36: Synthesis of Compound 702

[0374]

[0375] Preparation of C-702: Following the same preparation method as compound A-376 in Synthesis Example 11, replace d-376 with an equal molar amount of d-702. The remaining steps were the same to obtain C-702 (37.74 g). The purity of the solid was ≥99.92% as determined by HPLC. Mass spectrum: m / z: 353.1996 (theoretical value: 353.1982).

[0376] Compound 702 (14.89 g) was obtained by the same preparation method as in Example 3, except that A-137 and C-137 were replaced with equal moles of A-524 and C-702, respectively. The remaining steps were the same. The purity of the solid was ≥99.90% as determined by HPLC. Mass spectrum m / z: 698.2851 (theoretical value: 698.2866). Theoretical element content (%): C 48 H 38 N4Si: C, 82.49; H, 5.48; N, 8.02. Measured element content (%): C, 82.47; H, 5.46; N, 8.04.

[0377] Synthesis Example 37: Synthesis of Compound 723

[0378]

[0379] Following the same preparation method as in Example 3 for compound 137, A-137 and B-137 were replaced with equal moles of A-723 and B-291, respectively, and the remaining steps were the same to obtain compound 723 (14.61 g). HPLC analysis of the solid showed a purity of ≥99.91%. Mass spectrum m / z: 695.2775 (theoretical value: 695.2757). Theoretical element content (%): C 49 H 37 N3Si: C, 84.57; H, 5.36; N, 6.04. Measured element content (%): C, 84.58; H, 5.38; N, 6.01.

[0380] Synthesis Example 38: Synthesis of Compound 727

[0381]

[0382] Following the same preparation method as that of Compound 137 in Synthesis Example 3, A-137, B-137, and C-137 were replaced with equal moles of A-727, B-291, and C-172, respectively. Other steps were the same to obtain Compound 727 (14.72 g). HPLC analysis of the solid showed a purity of ≥99.90%. Mass spectrum m / z: 700.3052

[0383] (Theoretical value: 700.3071). Theoretical element content (%) C 49 H 32 D5N3Si: C, 83.96; H, 6.04; N, 5.99. Measured element content (%): C, 83.94; H, 6.06; N, 5.96.

[0384] Synthesis Example 39: Synthesis of Compound 742

[0385]

[0386] Following the same preparation method as compound 137 in Example 3, A-137, B-137, and C-137 were replaced with equal moles of C-172, B-172, and C-172, respectively, and the other steps were the same to obtain compound 742 (15.81 g). The solid purity was ≥99.92% as determined by HPLC. Mass spectrum m / z: 721.3316

[0387] (Theoretical value: 721.3309). Theoretical element content (%) C 48 H 47 N3Si2: C, 79.84; H, 6.56; N, 5.82. Measured element content (%): C, 79.81; H, 6.58; N, 5.83.

[0388] Synthesis Example 40: Synthesis of Compound 757

[0389]

[0390] Compound 757 (14.60 g) was obtained by the same preparation method as in Example 3, except that A-137 and B-137 were replaced with equal moles of C-137 and B-757, respectively. HPLC analysis of the solid showed a purity of ≥99.91%. Mass spectrum: m / z: 694.2961 (theoretical value: 694.2948). Theoretical element content (%): C 45 H 42 N4Si2: C, 77.77; H, 6.09; N, 8.06. Measured element content (%): C, 77.75; H, 6.06; N, 8.09.

[0391] Synthesis Example 41: Synthesis of Compound 519

[0392]

[0393] Compound 519 (11.18 g) was obtained by the same preparation method as in Example 3, except that A-137 and B-137 were replaced with equal moles of A-524 and B-172, respectively. HPLC analysis of the solid showed a purity of ≥99.94%. Mass spectrum: m / z: 497.2275 (theoretical value: 497.2287). Theoretical element content (%): C 33 H 31 N3Si: C, 79.64; H, 6.28; N, 8.44. Measured element content (%): C, 79.66; H, 6.25; N, 8.47.

[0394] Synthesis Example 42: Synthesis of Compound 748

[0395]

[0396] Compound 716 (15.51 g) was obtained by the same preparation method as in Example 3, except that A-137 and B-137 were replaced with equal moles of A-524 and B-291, respectively. The remaining steps were the same. The purity of the solid was ≥99.95% as determined by HPLC. Mass spectrum: m / z: 693.2982 (theoretical value: 693.2996). Theoretical element content (%): C 46 H 43 N3Si2: C, 79.61; H, 6.25; N, 6.05. Measured element content (%): C, 79.66; H, 6.23; N, 6.08.

[0397] Synthesis Example 43: Synthesis of Compound 2-73

[0398]

[0399] Synthetic intermediate I-2-73

[0400] Under nitrogen, a-2-73 (10.81 g, 40 mmol), b-2-73 (13.54 g, 80 mmol), sodium tert-butoxide (11.53 g, 120 mmol), and Pd(dppf)Cl2 (0.29 g, 0.4 mmol) were added to a reaction flask. The mixture was then dissolved in 260 mL of toluene. The air was replaced with nitrogen three times, and the mixture was heated under reflux for 7.5 hours. The reaction was monitored by TLC until complete. The mixture was cooled to room temperature, filtered through celite, and the filtrate was concentrated by vacuum distillation. The mixture was purified by column chromatography (petroleum ether / ethyl acetate = 10:1) to obtain intermediate I-2-73 (11.80 g, 66% yield). The solid purity was ≥99.82% as determined by HPLC. Mass spectrum: m / z: 446.1561 (theoretical value: 446.1550).

[0401] Synthesis of compound 2-73

[0402] Under nitrogen protection, intermediate I-2-73 (8.94 g, 20 mmol), c-2-73 (4.91 g, 20 mmol), sodium tert-butoxide (3.84 g, 40 mmol), Pd2(dba)3 (0.18 g, 0.20 mmol), x-phos (0.19 g, 0.4 mmol) were added to the reaction flask, and then xylene (150 mL) was added to dissolve it. After nitrogen replaced the air three times, the reaction was heated under reflux for 6 hours. The reaction was observed by TLC until the reaction was complete. It was naturally cooled to room temperature, filtered, and the obtained crude product was recrystallized from toluene to obtain compound 2-73 (9.31 g, yield 71%). The solid purity was determined by HPLC to be ≥99.94%. Mass spectrum m / z: 655.2997 (theoretical value: 655.2987). Theoretical element content (%) C 48 H 37 N3: C, 87.91; H, 5.69; N, 6.41. Measured element content (%): C, 87.90; H, 5.66; N, 6.45.

[0403] Synthesis Example 44: Synthesis of Compound 2-82

[0404]

[0405] Compound 2-73 was synthesized using the same method as in Example 43, except that C-2-73 was replaced with an equal molar amount of C-2-82 to synthesize Compound 2-82 (11.85 g). The purity of the solid was ≥99.96% as determined by HPLC. Mass spectrum m / z: 789.4072 (theoretical value: 789.4083). Theoretical element content (%): C 58 H 51N3: C, 88.17; H, 6.51; N, 5.32. Measured element content (%): C, 88.13; H, 6.49; N, 5.30.

[0406] Synthesis Example 45: Synthesis of Compound 2-149

[0407]

[0408] Compound 2-73 was synthesized using the same method as in Example 43, except that b-2-73 was replaced with an equal molar amount of c-2-73, and c-2-73 was replaced with an equal molar amount of b-2-73. Compound 2-149 (10.54 g) was synthesized. The purity of the solid was ≥99.98% as determined by HPLC. Mass spectrum m / z: 731.3319 (theoretical value: 731.3300). Theoretical element content (%): C 54 H 41 N3: C, 88.61; H, 5.65; N, 5.74. Measured element content (%): C, 86.64; H, 5.63; N, 5.73.

[0409] Synthesis Example 46: Synthesis of Compound 2-162

[0410]

[0411] Compound 73 was synthesized using the same method as in Example 43, except that b-2-73 was replaced with an equal molar amount of c-2-73, and c-2-73 was replaced with an equal molar amount of c-2-162. Compound 2-162 (11.96 g) was synthesized. The purity of the solid was ≥99.96% as determined by HPLC. Mass spectrum m / z: 807.3606 (theoretical value: 807.3613). Theoretical element content (%): C 60 H 45 N3: C, 89.19; H, 5.61; N, 5.20. Measured element content (%): C, 89.23; H, 5.59; N, 5.18.

[0412] Synthesis Example 47: Synthesis of Compound 2-180

[0413]

[0414] Compound 2-73 was synthesized using the same method as in Example 43, except that b-2-73 was replaced with an equal molar amount of c-2-73, and c-2-73 was replaced with an equal molar amount of c-2-180. Compound 2-180 (12.55 g) was synthesized. The purity of the solid was ≥99.97% as determined by HPLC. Mass spectrum m / z: 883.3938 (theoretical value: 883.3926). Theoretical element content (%): C 66H 49 N3: C, 89.66; H, 5.59; N, 4.75. Measured element content (%): C, 89.64; H, 5.57; N, 4.79.

[0415] Synthesis Example 48: Synthesis of Compound 2-351

[0416]

[0417] Compound 2-73 was synthesized using the same method as in Example 43, except that a-2-73 was replaced with an equal molar amount of a-2-351, b-2-73 was replaced with an equal molar amount of b-2-351, and c-2-73 was replaced with an equal molar amount of b-2-73 to synthesize compound 2-351 (13.09 g). The purity of the solid was ≥99.95% as determined by HPLC. Mass spectrum m / z: 883.3933 (theoretical value: 883.3926). Theoretical element content (%): C 66 H 49 N3: C, 89.66; H, 5.59; N, 4.75. Measured element content (%): C, 89.68; H, 5.60; N, 4.72.

[0418] Synthesis Example 49: Synthesis of Compound 2-391

[0419]

[0420] Compound 2-73 was synthesized using the same method as in Example 43, except that b-2-73 was replaced with an equal molar amount of c-2-73, and c-2-73 was replaced with an equal molar amount of c-2-391. Compound 2-391 (12.21 g) was synthesized. The purity of the solid was ≥99.94% as determined by HPLC. Mass spectrum m / z: 847.3916 (theoretical value: 847.3926). Theoretical element content (%): C 63 H 49 N3: C, 89.22; H, 5.82; N, 4.95. Measured element content (%): C, 89.27; H, 5.81; N, 4.91.

[0421] Synthesis Example 50: Synthesis of Compound 2-597

[0422]

[0423] Compound 2-73 was synthesized using the same method as in Example 43, except that b-2-73 was replaced with an equal molar amount of c-2-73, and c-2-73 was replaced with an equal molar amount of c-2-597. Compound 2-597 (11.27 g) was synthesized. The purity of the solid was ≥99.96% as determined by HPLC. Mass spectrum m / z: 771.3266 (theoretical value: 771.3250). Theoretical element content (%): C 56 H 41 N3O: C, 87.13; H, 5.35; N, 5.44. Measured element content (%): C, 87.18; H, 5.33; N, 5.41.

[0424] Synthesis Example 51: Synthesis of Compound 2-641

[0425]

[0426] Compound 2-73 was synthesized using the same method as in Example 43, except that b-2-73 was replaced with an equal molar amount of c-2-73, and c-2-73 was replaced with an equal molar amount of c-2-641. Compound 2-641 (14.16 g) was synthesized. The purity of the solid was ≥99.97% as determined by HPLC. Mass spectrum m / z: 943.3044 (theoretical value: 943.3055). Theoretical element content (%): C 66 H 45 N3S2: C, 83.96; H, 4.80; N, 4.45. Measured element content (%): C, 83.90; H, 4.83; N, 4.48.

[0427] Synthesis Example 52: Synthesis of Compound 2-779

[0428]

[0429] Compound 2-73 was synthesized using the same method as in Example 43, except that b-2-73 was replaced with an equal molar amount of b-2-779 and c-2-73 was replaced with an equal molar amount of c-2-180. Compound 2-779 (13.50 g) was synthesized. The purity of the solid was ≥99.98% as determined by HPLC. Mass spectrum m / z: 911.3520 (theoretical value: 911.3512). Theoretical element content (%): C 66 H 45 N3O2: C, 86.91; H, 4.97; N, 4.61. Measured element content (%): C, 86.90; H, 4.96; N, 4.63.

[0430] Synthesis Example 53: Synthesis of Compound 2-783

[0431]

[0432] Compound 2-73 was synthesized using the same method as in Example 43, except that b-2-73 was replaced with an equal molar amount of b-2-783 and c-2-73 was replaced with an equal molar amount of b-2-73 to synthesize compound 2-783 (11.69 g). The purity of the solid was ≥99.97% as determined by HPLC. Mass spectrum m / z: 811.3179 (theoretical value: 811.3199). Theoretical element content (%): C 58 H 41 N3O2: C, 85.79; H, 5.09; N, 5.18. Measured element content (%): C, 85.73; H, 5.07; N, 5.14.

[0433] Device Examples

[0434] Test Method: Driving voltage and luminous efficiency were measured using a combined IVL test system consisting of test software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectrum scanning luminance meter. Lifespan was measured using a McScience M6000 OLED Lifespan Test System.

[0435] Test conditions: The test environment is atmospheric environment and the temperature is room temperature. The service life of the device prepared by the present invention is tested (the brightness decays to 95% of the initial brightness). The current density during the test is 10mA / cm 2 .

[0436] The materials used in preparing the organic electroluminescent device and the comparative device are as follows:

[0437]

[0438] Device Example 1: Preparation of a blue organic electroluminescent device

[0439] The ITO transparent glass substrate was ultrasonically cleaned twice with 5% glass cleaning solution for 20 minutes each time, then ultrasonically cleaned twice with deionized water for 10 minutes each time, and then ultrasonically cleaned with acetone and isopropyl ketone for 20 minutes each time, and dried at 120°C. A mixed material of HI-P and HT-1 (HI-P: HT-1 mass ratio = 3:97) was vacuum evaporated on an ITO transparent glass substrate as a hole injection layer with a deposition thickness of 10 nm, HT-1 was vacuum evaporated on the hole injection layer as a hole transport layer with a deposition thickness of 120 nm, a mixed material of BH-1 and BD-1 (BH-1: BD-1 mass ratio = 98:2) was evaporated on the hole transport layer to form a light-emitting layer with a deposition thickness of 30 nm, and then HB-1 was vacuum evaporated on the light-emitting layer as a hole blocking layer with a deposition thickness of 10 nm, and then a mixed material of the present invention compound 8 and Liq (compound 8: Liq mass ratio = 1:1) was evaporated on the hole blocking layer as an electron transport layer with a deposition thickness of 30 nm, and then LiF with a thickness of 1 nm was evaporated as an electron injection layer, and Al was vacuum evaporated on the electron injection layer as a cathode with a deposition thickness of 100 nm.

[0440] Device Examples 2 to 42: Preparation of Blue Organic Electroluminescent Devices

[0441] The compounds listed in Table 1 were used to replace Compound 8 in Device Example 1 as the electron transport layer, and the rest of the manufacturing process was exactly the same to prepare an organic electroluminescent device.

[0442] Comparative Examples 1 to 7: Preparation of Blue Organic Electroluminescent Devices

[0443] D-1, D-2, D-3, D-4, D-5, D-8 and D-10 were used to replace compound 8 in device example 1 as electron transport layers, respectively, and the rest of the preparation process was exactly the same to prepare organic electroluminescent devices.

[0444] Table 1: Luminescence characteristics test data of the organic electroluminescent devices prepared in device examples 1 to 42 and comparative device examples 1 to 7

[0445]

[0446]

[0447] According to the test structures in Table 1, compared with the comparative compounds, when the compounds of the present invention are used as electron transport layer materials of organic electroluminescent devices, the driving voltage is further improved, and the luminous efficiency and life are significantly improved.

[0448] Device Example 43: Preparation of Red Organic Electroluminescent Device

[0449] The ITO transparent glass substrate was ultrasonically cleaned twice with 5% glass cleaning solution for 20 minutes each time, and then ultrasonically cleaned twice with deionized water for 10 minutes each time. It was ultrasonically cleaned with acetone and isopropyl ketone for 20 minutes in sequence and dried at 120°C. A mixed material of HI-P and HT-1 (HI-P: HT-1 mass ratio = 3:97) was vacuum evaporated on the ITO transparent glass substrate as a hole injection layer with a thickness of 10 nm. HT-1 was vacuum evaporated on the hole injection layer as the first hole transport layer with a thickness of 120 nm. HT-2 was evaporated on the hole transport layer as the second hole transport layer with a thickness of 70 nm. A mixed material of RH-1, RH-2 and RD-1 (RH-1: RH-2: RD-1) was evaporated on the second hole transport layer. 1 mass ratio = 49:49:2) to form a light-emitting layer, the light-emitting layer having a vapor deposition thickness of 20 nm, and then vacuum-depositing the compound 8 of the present invention on the light-emitting layer as a hole blocking layer with a vapor deposition thickness of 10 nm, and then vapor-depositing a mixed material of ET-1 and Liq (compound ET-1: Liq mass ratio = 1:1) on the hole blocking layer as an electron transport layer with a vapor deposition thickness of 30 nm, and then vapor-depositing LiF with a thickness of 1 nm as an electron injection layer, and vacuum-depositing Al as a cathode on the electron injection layer with a vapor deposition thickness of 100 nm.

[0450] Device Examples 43-82: Preparation of Red Organic Electroluminescent Devices

[0451] The compounds listed in Table 2 were used instead of Compound 8 in Device Example 43 as the hole blocking layer, and the rest of the manufacturing process was exactly the same to prepare an organic electroluminescent device.

[0452] Comparative Examples 8-10: Preparation of Red Organic Electroluminescent Devices

[0453] D-5, D-6 and D-7 were used to replace compound 8 in device example 43 as hole blocking layers respectively, and the rest of the manufacturing process was exactly the same to prepare organic electroluminescent devices.

[0454] Table 2: Luminescence characteristics test data of the organic electroluminescent devices prepared in device examples 43 to 82 and comparative device examples 8 to 10

[0455]

[0456]

[0457] According to the test structures in Table 2, compared with the comparative compounds D-5, D-6, and D-7, when the compounds of the present invention are used as hole blocking layer materials for organic electroluminescent devices, the driving voltage is further improved, and the luminous efficiency and life are significantly improved.

[0458] Device Example 83: Preparation of a Blue Organic Electroluminescent Device

[0459] The ITO transparent glass substrate was ultrasonically cleaned twice with 5% glass cleaning solution for 20 minutes each time, then ultrasonically cleaned twice with deionized water for 10 minutes each time, and then ultrasonically cleaned with acetone and isopropyl ketone for 20 minutes each time, and dried at 120°C. A mixed material of HI-P and HT-1 (HI-P: HT-1 mass ratio = 3:97) was vacuum evaporated on an ITO transparent glass substrate as a hole injection layer with a deposition thickness of 10 nm, 2-219 was vacuum evaporated on the hole injection layer as a hole transport layer with a deposition thickness of 120 nm, a mixed material of BH-1 and BD-1 (BH-1: BD-1 mass ratio = 98:2) was evaporated on the hole transport layer to form a light-emitting layer with a deposition thickness of 30 nm, and then HB-1 was vacuum evaporated on the light-emitting layer as a hole blocking layer with a deposition thickness of 10 nm, and then a mixed material of the present invention compound 8 and Liq (compound 8: Liq mass ratio = 1:1) was evaporated on the hole blocking layer as an electron transport layer with a deposition thickness of 30 nm, and then LiF with a thickness of 1 nm was evaporated as an electron injection layer, and Al was vacuum evaporated on the electron injection layer as a cathode with a deposition thickness of 100 nm.

[0460] Device Examples 84 to 132: Preparation of Blue Organic Electroluminescent Devices

[0461] The compounds listed in Table 3 were used to replace Compound 8 as the electron transport layer and Compound 2-219 as the hole transport layer in Device Example 83, respectively. The rest of the preparation process was exactly the same to prepare an organic electroluminescent device.

[0462] Comparative Examples 11-21: Preparation of Blue Organic Electroluminescent Devices

[0463] The compounds listed in Table 3 were used to replace Compound 8 as the electron transport layer and Compound 2-219 as the hole transport layer in Device Example 83, respectively. The rest of the preparation process was exactly the same to prepare an organic electroluminescent device.

[0464] Table 3: Luminescence characteristics test data of the organic electroluminescent devices prepared in device examples 83 to 132 and comparative device examples 11 to 21

[0465]

[0466]

[0467] According to the results in Table 3, when the compound of Formula 1 and the compound of Formula 2 according to the present invention are used in the electron transport layer and the hole transport layer of the organic electroluminescent device, the carrier transport balance can be effectively improved, the recombination rate of holes and electrons in the light-emitting layer can be increased, and the local voltage is too high to cause the device power consumption to increase, thereby improving the luminous efficiency and life of the organic electroluminescent device.

[0468] Device Example 133: Preparation of Red Organic Electroluminescent Device

[0469] The ITO transparent glass substrate was ultrasonically cleaned twice with 5% glass cleaning solution for 20 minutes each time, and then ultrasonically cleaned twice with deionized water for 10 minutes each time. Use acetone and isopropyl tone to ultrasonically clean for 20 minutes in sequence, and dry at 120°C. A mixed material of HI-P and HT-1 (HI-P: HT-1 mass ratio = 3:97) was vacuum evaporated on the ITO transparent glass substrate as a hole injection layer with a thickness of 10nm. HT-1 was vacuum evaporated on the hole injection layer as the first hole transport layer with a thickness of 120nm. The compound 2-351 of the present invention was evaporated on the hole transport layer as the second hole transport layer with a thickness of 70nm. A mixed material of RH-1, RH-2 and RD-1 (RH-1: RH-2: The luminescent layer was formed by vacuum vapor deposition of the compound 8 of the present invention on the luminescent layer as a hole blocking layer with a thickness of 10 nm, and then a mixed material of ET-1 and Liq (compound ET-1: Liq mass ratio = 1:1) was evaporated on the hole blocking layer as an electron transport layer with a thickness of 30 nm, and then LiF with a thickness of 1 nm was evaporated as an electron injection layer, and Al was vacuum evaporated on the electron injection layer as a cathode with a thickness of 100 nm.

[0470] Device Examples 134-156: Preparation of Red Organic Electroluminescent Devices

[0471] The compounds listed in Table 4 were used to replace Compound 8 in Device Example 133 as the hole blocking layer and Compound 2-351 as the second hole transport layer, respectively. The rest of the manufacturing process was exactly the same to prepare an organic electroluminescent device.

[0472] Comparative Examples 22-27: Preparation of Red Organic Electroluminescent Devices

[0473] The compounds listed in Table 4 were used to replace Compound 8 in Device Example 133 as the hole blocking layer and Compound 2-351 as the second hole transport layer, respectively. The rest of the manufacturing process was exactly the same to prepare an organic electroluminescent device.

[0474] Table 4: Luminescence characteristics test data of the organic electroluminescent devices prepared in device examples 133 to 156 and comparative device examples 22 to 27

[0475]

[0476]

[0477] According to the results in Table 4, when the compound of Formula 1 and the compound of Formula 2 according to the present invention are used in combination in the hole blocking layer and the second hole transport layer of an organic electroluminescent device, holes and electrons can be effectively blocked from diffusing to the interface of the light-emitting layer, and electrons and holes can be effectively confined within the light-emitting layer, thereby increasing the recombination rate of holes and electrons in the light-emitting layer, thereby improving the luminous efficiency and life of the organic electroluminescent device.

[0478] It should be noted that the present invention is particularly described using individual embodiments. However, without departing from the principles of the present invention, a person skilled in the art may make various improvements in form or detail to the present invention, and these improvements also fall within the scope of protection of the present invention.

Claims

1. A heterocyclic compound, characterized in that The heterocyclic compound has a structure represented by Formula 1: In Formula 1, R1 and R2 are independently selected from hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and any one of the following groups: The R 14 Any one independently selected from hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl; The m1 is independently selected from 1, 2, 3 or 4, the m2 is independently selected from 1, 2 or 3, the m3 is independently selected from 1, 2, 3, 4, 5 or 6, and the m4 is independently selected from 1, 2, 3, 4 or 5; or R1 and R2 are connected to form the following ring structure: R3 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; Said n1 is independently selected from 1, 2, 3 or 4, Said Z is independently selected from C(R4) or N; The ring E is selected from any one of the following groups: Said V is independently selected from C(R5) or N; R4 and R5 are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C12 aryl, and substituted or unsubstituted C2-C30 heteroaryl; the substituted groups in R4 and R5 are selected from any one of deuterium, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C3-C12 cycloalkyl; The X is independently selected from C(R6) or N; and at least one X is selected from N; the R6 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; The L1 is independently selected from any one of the following groups: The Y is independently selected from C(R7) or N, and the R7 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C3-C12 cycloalkyl; or two adjacent R7s are connected to form any one of a substituted or unsubstituted C3-C7 aliphatic ring or a benzene ring; The R0 is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C3-C12 cycloalkyl; The Ar1 is independently selected from any one of the following groups: The Q is independently selected from C(R 10 ) or N, said R 10 Any one independently selected from hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl; or two adjacent R 10 They are connected to form a substituted or unsubstituted C3-C7 aliphatic ring; The R8 is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; The R9 is selected from any one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C2-C30 heteroaryl group; The L2 is independently selected from any one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted pyridylene group, and a substituted or unsubstituted pyrimidylene group; The "substituted" group in L2 is selected from any one of deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C3-C12 cycloalkyl; Ar2 and Ar3 are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; t is selected from 1 or 2; The X0 is independently selected from O, S, C (R 11 R 12 ) or N(R 13 ); The R 11 、R 12 、R 13 independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

2. The heterocyclic compound according to claim 1, characterized in that The heterocyclic compound is selected from any one of Formula 1-1 to Formula 1-7: The definitions of R1, R2, Z, E, R6, L1, R0, and Ar1 are the same as those in Formula 1.

3. The heterocyclic compound according to claim 1 or 2, characterized in that described Any one selected from the following groups: R1 and R2 are independently selected from hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted any one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, or any one of the following groups: The R 14 、R 14 'Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl; The m1 is independently selected from 1, 2, 3 or 4, the m2 is independently selected from 1, 2 or 3, the m3 is independently selected from 1, 2, 3, 4, 5 or 6, the m4 is independently selected from 1, 2, 3, 4 or 5, the m5 is independently selected from 1, 2, 3, 4, 5, 6 or 7, and the m6 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8; R3 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; R4 and R5 are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted trimethylsilyl, triethylsilyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, benzofuranyl, and benzothiophenyl; The n1 is independently selected from 1, 2, 3 or 4, the n2 is independently selected from 1, 2 or 3, the n3 is independently selected from 1, 2, 3, 4, 5 or 6, the n4 is independently selected from 1, 2, 3, 4 or 5, and the n5 is independently selected from 1 or 2.

4. The heterocyclic compound according to claim 1, characterized in that The L1 is independently selected from any one of the following groups: The R7 and R7' are independently selected from hydrogen, deuterium, cyano, nitro, halogen, or any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl; The a1 is independently selected from 1, 2, 3 or 4, the a2 is independently selected from 1, 2 or 3, the a3 is independently selected from 1 or 2, the a4 is independently selected from 1, 2, 3, 4, 5 or 6, the a5 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8, and the a6 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

5. The heterocyclic compound according to claim 1, characterized in that The Ar1 is independently selected from any one of the following groups: The R 10 、R 10 'Independently selected from hydrogen, deuterium, cyano, nitro, halogen, or any one of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornane, Si(R0)3; The R 15 independently selected from hydrogen, deuterium, cyano, nitro, halogen, or any one of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornane, Si(R0)3, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, phenyl, biphenyl; The R 11 、R 12 independently selected from hydrogen, deuterium, cyano, nitro, halogen, or any one of the following groups which may be substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornane, Si(R0)3, phenyl, biphenyl; The R 13 independently selected from hydrogen, deuterium, cyano, nitro, halogen, or any one of the following groups which may be substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornane, Si(R0)3, phenyl, biphenyl, naphthyl; Ar3 is independently selected from hydrogen, deuterium, cyano, nitro, halogen, or any one of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornane, Si(R0)3, phenyl, biphenyl, naphthyl; The b1 is independently selected from 1, 2, 3, 4 or 5, the b2 is independently selected from 1, 2 or 3, the b3 is independently selected from 1 or 2, the b4 is independently selected from 1, 2, 3 or 4, the b5 is independently selected from 1, 2, 3, 4, 5 or 6, the b6 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8, the b7 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, the b8 is independently selected from 1, 2, 3, 4, 5, 6 or 7, and the b9 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9.

6. The heterocyclic compound according to claim 1, 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, the organic layer comprises an electron transport region, a light-emitting layer, and a hole transport region, wherein the electron transport region is located between the light-emitting layer and the cathode, and the hole transport region is located between the light-emitting layer and the anode, characterized in that: The electron transport region comprises any one of the heterocyclic compounds according to any one of claims 1 to 6.

8. The organic electroluminescent device according to claim 7, characterized in that: The hole transport region comprises a triarylamine compound represented by Formula 2: In Formula 2, Ara1, Ara2, Ara3, Ara4, Ara5, and Ara6 are independently selected from any one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C2-C30 heteroaryl groups; The La1, La2, La3, La4, La5, and La6 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C2-C30 heteroarylene group; The Lb, Lc, and Ld are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C2-C30 heteroarylene group; The Ra is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, 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; The q is selected from 1, 2 or 3.

9. The organic electroluminescent device according to claim 8, characterized in that: The Ara1, Ara2, Ara3, Ara4, Ara5, and Ara6 are independently selected from any one of the following groups: Said W1 is independently selected from O, S, C(RcRd) or N(Re); said W2 is independently selected from O, S, C(RfRg) or N(Rh); said W3 is independently selected from O, S or N(Ri); The Rb and Rb' are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, 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 Rb's are connected to form a substituted or unsubstituted ring; The Rc, Rd, Rf, and Rg are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, 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; or Rc and Rd are connected to form a substituted or unsubstituted ring; or Rf and Rg are connected to form a substituted or unsubstituted ring; The Re, Rh, and Ri are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, 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; The q1 is independently selected from 1, 2, 3, 4 or 5, the q2 is independently selected from 1, 2, 3 or 4, the q3 is independently selected from 1, 2 or 3, the q4 is independently selected from 1 or 2, the q5 is independently selected from 1, 2, 3, 4, 5 or 6, the q6 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8, the q7 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, the q8 is independently selected from 1, 2, 3, 4, 5, 6 or 7, the q9 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9, the q 10 are independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11.

10. The organic electroluminescent device according to claim 8, characterized in that: The formula 2 is selected from any one of the following structures:

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