Heterocyclic compound and organic electroluminescent element comprising same

Abstract

The invention belongs to the technical field of photoelectric materials, and relates to a heterocyclic compound and an organic electroluminescent element comprising the same. The organic compound has a structure represented by formula (1): # imgabs0 #, the heterocyclic compound has an azole ring (imidazole ring, oxazole ring, thiazole ring) condensed phenanthridine structure, and when the organic compound is used in an N-type charge generation layer, a nitrogen atom of the organic compound is bonded or bonded to an alkali metal or alkaline earth metal as a dopant in the N-type charge generation layer to form an energy gap state, and a nitrogen atom of the organic compound is bonded or bonded to an alkali metal or alkaline earth metal as a dopant in the N-type charge generation layer. Furthermore, the electron transmission characteristic from the N-type charge generation layer to the electron transmission layer is improved. According to the compound, the electron injection and transmission capability is improved; the organic electroluminescent element prepared by using the compound can realize durable service life and has higher current efficiency.

Description

Technical Field

[0001] The invention belongs to the technical field of optoelectronic materials, and particularly relates to a heterocyclic compound and an organic electroluminescent element containing the heterocyclic compound. Background Art

[0002] OLEDs emit light by the cancellation of hole-electron pairs generated when holes and electrons are injected from a hole injection electrode (anode) and an electron injection electrode (cathode) into an emitting material layer (EML) disposed between the anode and the cathode. Such OLEDs can be formed on flexible transparent substrates such as plastics, can also operate at low voltages (below 10V), consume relatively low power, and provide excellent colors.

[0003] Generally, OLEDs can be divided into single-stack type and stacked type. In order to achieve a long-life OLED, a tandem OLED, that is, an OLED having a stacked structure of multiple light-emitting units, is mainly used. For example, a tandem white light OLED includes a first light-emitting stack including a blue light-emitting layer and a second light-emitting stack including a yellow-green light-emitting layer, wherein the first light-emitting stack and the second light-emitting stack are stacked vertically. This white light OLED emits white light by mixing the light emitted from the blue light-emitting layer and the light emitted from the yellow-green light-emitting layer. The stacked OLED includes a charge generation layer disposed between the first light-emitting stack and the second light-emitting stack to improve the current efficiency in each light-emitting layer while ensuring that the charge is effectively distributed to the light-emitting stack. Generally, the charge generation layer has a PN junction, in which an N-type charge generation layer and a P-type charge generation layer are stacked in sequence.

[0004] In such a charge generation layer used in a commonly used tandem OLED, due to the energy level difference between the N-type charge generation layer and the P-type charge generation layer, charges are generated at the interface between the P-type charge generation layer and the adjacent hole injection layer or hole transport layer, resulting in degradation of electron injection in the N-type charge generation layer.

[0005] When the N-type charge generation layer is doped with metal, the metal may diffuse into the P-type charge generation layer, resulting in a reduced lifespan of the OLED. In particular, common materials used for the charge generation layer do not have sufficient thermal / electrical stability. Therefore, long-term operation of the OLED leads to degradation or deterioration of the materials used for the charge generation layer. As a result, not only is the efficiency of electron injection from the interface between the P-type charge generation layer and the adjacent hole injection layer or hole transport layer to the N-type charge generation layer significantly reduced, but the efficiency of electron injection from the N-type charge generation layer to the adjacent electron transport layer is also significantly reduced, resulting in reduced performance and lifespan of the OLED.

[0006] Therefore, a compound is needed so that an organic electroluminescent element prepared by the compound can have a longer service life and good current efficiency. Summary of the invention

[0007] The object of the present invention is to provide a heterocyclic compound, wherein an organic electroluminescent element prepared by using the heterocyclic compound can achieve a durable service life and good current efficiency.

[0008] The technical solution adopted by the present invention to solve its technical problem is:

[0009] A heterocyclic compound having a structure shown in formula (1):

[0010] in

[0011] represents a double bond or a single bond,

[0012] X 1 Selected from O, S, N, NR,

[0013] X 2 Selected from O, S, N, NR,

[0014] L 1 -L 6 are independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group,

[0015] R, R 1 -R 6 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C3-C60 heterocyclyl,

[0016] The substituents in the substitution or unsubstitution are each independently selected from one or a combination of deuterium, halogen, cyano, C1-C10 alkyl, C6-C30 aryl, C3-C30 heteroaryl.

[0017] Preferably, in formula (1), One of them is a single bond and the other is a double bond.

[0018] Preferably, the heteroatom of the heteroaryl, heteroarylene or heterocyclic group is selected from O, S, N, P or Si.

[0019] Preferably, L 1 -L 6and independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group, wherein the heteroatom of the heteroarylene group is selected from O or S.

[0020] Preferably, L 1 -L 6 and independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group.

[0021] Preferably, L 1 -L 6 and independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group, wherein the heteroatom of the heteroarylene group is selected from O or S.

[0022] Preferably, the heterocyclic compound is selected from the compounds represented by the following formula (1-1) or formula (1-2):

[0023]

[0024] Preferably, in the compound represented by formula (1-1), X 1 Selected from NR;

[0025] Preferably, in the compound represented by formula (1-2), X 2 Selected from NR;

[0026] Preferably, in the compound represented by formula (1-2), X 2 Selected from O, S;

[0027] Preferably, R, L 1 R 1 , L 2 R 2 , L 3 R 3 , L 4 R 4 , L 5 R 5 , L 6 R 6 At least two of are not hydrogen;

[0028] Preferably, R, L 1 R 1 , L 2 R 2 , L 3 R 3 , L 4 R 4 , L 5 R 5 , L 6 R 6 Neither of them is hydrogen;

[0029] Preferably, R, L 1 R 1 , L 2 R 2 , L 3 R 3 , L 4 R 4 , L 5 R 5 , L 6 R 6 Two of them are not hydrogen, and the others are selected from hydrogen;

[0030] Preferably, R, L 1 R 1 , L 2 R 2 , L 3 R 3 , L 4 R 4 , L 5 R 5 , L 6 R 6 At least one of is not hydrogen;

[0031] Preferably, L 1 R 1 Not hydrogen;

[0032] Preferably, R, L 1 R 1 None of them are hydrogen;

[0033] More preferably, R, L 1 R 1 All are not hydrogen, L 2 R 2 , L 3 R 3 , L 4 R 4 , L 5 R 5 , L 6 R 6 All are hydrogen;

[0034] Preferably, L 1 R 1 , L 2 R 2 None of them are hydrogen;

[0035] More preferably, L 1 R 1 , L 2 R 2 All are not hydrogen; L 3 R 3 , L 4R 4 , L 5 R 5 , L 6 R 6 All are hydrogen;

[0036] Preferably, L 1 R 1 , L 3 R 3 None of them are hydrogen;

[0037] More preferably, L 1 R 1 , L 3 R 3 All are not hydrogen, L 2 R 2 , L 4 R 4 , L 5 R 5 , L 6 R 6 All are hydrogen;

[0038] Preferably, L 1 R 1 , L 4 R 4 None of them are hydrogen;

[0039] More preferably, L 1 R 1 , L 4 R 4 All are not hydrogen, L 2 R 2 , L 3 R 3 , L 5 R 5 , L 6 R 6 All are hydrogen;

[0040] Preferably, L 1 R 1 , L 5 R 5 None of them are hydrogen;

[0041] More preferably, L 1 R 1 , L 5 R 5 All are not hydrogen, L 2 R 2 , L 3 R 3 , L 4 R 4 , L 6 R 6 All are hydrogen;

[0042] Preferably, L 1 R 1 , L 6 R 6 None of them are hydrogen.

[0043] More preferably, L 1 R 1 , L 6 R 6 All are not hydrogen, L 2 R 2 , L 3 R 3 , L 4 R 4 , L 5 R 5 All are hydrogen.

[0044] As a preference, L 1 -L 6 The following groups are independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted phenylene naphthyl group, a substituted or unsubstituted binaphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted fluoranthenylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted benzopyrenylene group, a substituted or unsubstituted ... substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted pyridinylene;

[0045] R, R 1 -R 6 each independently selected from the following groups: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloadamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted indenyl, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted substituted or unsubstituted pyridyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl.

[0046] Furthermore, the substituents in the substituted or unsubstituted group are independently selected from one or more combinations of deuterium, halogen, cyano, C1-C10 alkyl, C6-C30 aryl, C3-C30 heteroaryl, and the substituted group may be substituted in one or more positions.

[0047] Furthermore, the substituents in the substitution or unsubstitution are each independently selected from one or more combinations of deuterium, halogen, cyano, phenyl, naphthyl, anthracenyl, phenanthryl, phenyl-substituted anthracenyl, pyrene, triphenylene, fluoranthene, dibenzofuranyl, dibenzothiophenyl, and carbazole.

[0048] The heterocyclic compound of the present invention is used as an organic electroluminescent element material.

[0049] The invention provides an organic electroluminescent element, comprising an anode, a cathode and an organic layer between the anode and the cathode, wherein the organic layer comprises the heterocyclic compound of the invention.

[0050] Preferably, the organic layer includes an electron transport layer and a light-emitting layer, and the electron transport layer contains the heterocyclic compound described in the present invention.

[0051] Preferably, the organic layer comprises at least two light-emitting units, a charge generation layer is comprised between the light-emitting units, the light-emitting units comprise an electron transport layer, and the at least one charge generation layer and / or at least one electron transport layer comprises the heterocyclic compound described in the present invention.

[0052] Preferably, the organic layer comprises more than or equal to two light-emitting units, a charge generation layer is comprised between the light-emitting units, the light-emitting units comprise an electron transport layer, the charge generation layer comprises an N-type charge generation layer and a P-type charge generation layer, and at least one of the N-type charge generation layer and the electron transport layer comprises the heterocyclic compound described in the present invention.

[0053] The electron transport layer comprises the electron transport layer of each light-emitting unit, and at least one of the N-type charge generation layer and the electron transport layer comprises the heterocyclic compound described in the present invention, which means that one N-type charge generation layer comprises the heterocyclic compound described in the present invention; or multiple N-type charge generation layers comprise the heterocyclic compound described in the present invention; or one electron transport layer in one light-emitting unit comprises the heterocyclic compound described in the present invention; or one N-type charge generation layer and one electron transport layer in one light-emitting unit comprise the heterocyclic compound described in the present invention; or one N-type charge generation layer and each electron transport layer in multiple light-emitting units comprise the heterocyclic compound described in the present invention; or multiple N-type charge generation layers and each electron transport layer in multiple light-emitting units comprise the heterocyclic compound described in the present invention, etc. When two or more layers comprise the heterocyclic compound described in the present invention, the heterocyclic compounds are the same or different.

[0054] The stacked structure of the present invention refers to n light-emitting units, where n is greater than or equal to 2, and the number of N-type charge generation layers is n-1.

[0055] An electronic device comprises the organic electroluminescent element of the present invention.

[0056] Compared with the prior art, the beneficial effects of the present invention are as follows: the heterocyclic compound of the present invention has an azole ring (imidazole ring, oxazole ring, thiazole ring) fused with a phenanthridine structure, and when used in an N-type charge generation layer, the nitrogen atom of the organic compound combines or bonds with an alkali metal or alkaline earth metal as a dopant in the N-type charge generation layer to form an energy gap state, thereby improving the electron transport characteristics from the N-type charge generation layer to the electron transport layer. The compound of the present invention improves the electron injection and transport capabilities; the organic electroluminescent element prepared using the compound can achieve a durable service life and has a higher current efficiency. BRIEF DESCRIPTION OF THE DRAWINGS

[0057] Figure 1 It is a schematic diagram of the structure of the organic electroluminescent element described in Application Example 1, wherein the first electrode layer 1, the hole injection layer 2, the hole transport layer 3, the light-emitting layer 4, the electron transport layer 5, the N-type charge generation layer 6, the P-type charge generation layer 7, the hole transport layer 8, the light-emitting layer 9, the electron transport layer 10, the electron injection layer 11 and the second electrode layer 12, wherein 100 is the first light-emitting unit and 200 is the second light-emitting unit.

[0058] Figure 21 is a schematic diagram of the structure of the organic electroluminescent element described in Application Example 2, wherein the first electrode layer 110 , the hole injection layer 120 , the hole transport layer 130 , the light-emitting layer 140 , the electron transport layer 150 , the electron injection layer 160 and the second electrode layer 170 . DETAILED DESCRIPTION

[0059] The technical solution of the present invention is further described in detail below through specific embodiments. It should be understood that the implementation of the present invention is not limited to the following embodiments, and any form of modification and / or change made to the present invention will fall within the protection scope of the present invention.

[0060] In the present invention, unless otherwise specified, all parts and percentages are by weight, and the equipment and raw materials used can be purchased from the market or are commonly used in the art. The methods in the following embodiments are all conventional methods in the art unless otherwise specified.

[0061] The reagents used in the following examples, unless otherwise specified, can be purchased from conventional biochemical reagent stores.

[0062] As used in the present invention, the term "halogen" may include fluorine, chlorine, bromine or iodine.

[0063] As used in the present invention, the term "C1-C10 alkyl" refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 10 carbon atoms, examples of which include but are not limited to methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl.

[0064] As used in the present invention, the term "C3-C10 cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 10 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, norbornyl, adamantane, and the like.

[0065] As used in the present invention, the term "C2-C10 heterocycloalkyl" is a monovalent substituent having a monocyclic or polycyclic ring of 2 to 10 carbon atoms, and the ring contains at least one heteroatom selected from O, S, N, P, and Si.

[0066] As used in the present invention, the term "alkoxy" refers to a straight chain, a branched chain or a cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited herein, but the alkoxy group preferably has 1 to 10 carbon atoms. Specific examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentyloxy, n-hexyloxy, and benzyloxy.

[0067] As used in the present invention, the term "C6-C60 aryl group" refers to a monovalent substituent derived from an aromatic hydrocarbon having a single ring or a combination of two or more rings and having 6 to 60 carbon atoms. Further, such an aryl group may have a form in which two or more rings are simply attached to each other or fused to each other. Examples of such aryl groups include, but are not limited to, phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, Pyrene fluorenyl, triphenylene, fluoranthenyl, dimethyl 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirobifluorenyl and the like.

[0068] As used herein, the term "arylene group" refers to a divalent aromatic group derived from an "aryl group" by removing a hydrogen atom. For example, a phenyl group is substituted by removing a hydrogen atom to form a phenylene group, and a naphthyl group is substituted by removing a hydrogen atom to form a naphthylene group.

[0069] As used in the present invention, the term "C3-C60 heteroaryl group" refers to a monovalent substituent derived from a monocyclic heterocyclic or polycyclic aromatic hydrocarbon having 3 to 60 carbon atoms. In this connection, at least one carbon, preferably 1 to 3 carbons in the ring are substituted with a heteroatom such as N, O, S, P, B or Si. In addition, this heteroaryl group may have a form in which two or more rings are simply lateral to each other or fused to each other or fused to an aromatic group. Examples of such heteroaryl groups include pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indolizinyl, indolyl, indolopyridinyl, purinyl, phenanthroline, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, thiazolyl, imidazolyl, oxazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzothiazolyl, benzimidazolyl, benzoxazolyl, carbazolyl, dibenzofuranyl, dibenzothienyl and the like, but the present invention is not limited thereto.

[0070] As used in the present invention, the term "heteroarylene" refers to a divalent heteroaryl group derived from a "heteroaryl" by removing a hydrogen atom. For example, a pyridyl group is derived from a pyridylene group by removing a hydrogen atom.

[0071] As used in the present invention, "L 1 R 1 "is hydrogen" means L 1 Selected from single bonds, R 1 Selected from hydrogen; "L 2 R 2 "is hydrogen" means L 2 Selected from single bonds, R 2 Selected from hydrogen; "L 3 R 3 "is hydrogen" means L 3 Selected from single bonds, R 3 Selected from hydrogen; "L 4 R 4 "is hydrogen" means L 4 Selected from single bonds, R 4Selected from hydrogen; "L 5 R 5 "is hydrogen" means L 5 Selected from single bonds, R 5 Selected from hydrogen; "L 6 R 6 "is hydrogen" means L 6 Selected from single bonds, R 6 Selected from hydrogen.

[0072] The present invention's "L 1 R 1 "Not hydrogen" means L 1 R 1 Medium 1 is not a single bond and R 1 Not hydrogen, or L 1 is not a single bond and R 1 is hydrogen, or L 1 is a single bond and R 1 Not hydrogen;

[0073] “L 2 R 2 "Not hydrogen" means L 2 R 2 Medium 2 is not a single bond and R 2 Not hydrogen, or L 2 is not a single bond and R 2 is hydrogen, or L 2 is a single bond and R 2 Not hydrogen;

[0074] “L 3 R 3 "Not hydrogen" means L 3 R 3 Medium 3 is not a single bond and R 3 Not hydrogen, or L 3 is not a single bond and R 3 is hydrogen, or L 3 is a single bond and R 3 Not hydrogen;

[0075] “L 4 R 4 "Not hydrogen" means L 4 R 4 Medium 4 is not a single bond and R 4 Not hydrogen, or L 4 is not a single bond and R 4 is hydrogen, or L 4 is a single bond and R 4 Not hydrogen;

[0076] “L 5 R5 "Not hydrogen" means L 5 R 5 Medium 5 is not a single bond and R 5 Not hydrogen, or L 5 is not a single bond and R 5 is hydrogen, or L 5 is a single bond and R 5 Not hydrogen;

[0077] “L 6 R 6 "Not hydrogen" means L 6 R 6 Medium 6 is not a single bond and R 6 Not hydrogen, or L 6 is not a single bond and R 6 is hydrogen, or L 6 is a single bond and R 6 Not hydrogen.

[0078] As used in the present invention, the "carbon number is AA-BB" in the expression "Z group having carbon atoms AA-BB" or "Z group having C(AA-BB)" means the carbon number of the Z group when it is unsubstituted, and does not include the carbon number of the substituent when it is substituted. For example, a C6-C30 aryl group means that when it is unsubstituted, the number of carbon atoms in the aryl group is any integer between 6 and 30, that is, the number of carbon atoms when it is unsubstituted can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20...30.

[0079] As used herein, the term "single bond" refers to a direct connection of groups, e.g. Medium 1 is a single bond, which means

[0080] As used in the present invention, the term "substituted or unsubstituted" means that the hydrogen atoms in the compound are replaced by non-hydrogen groups or are not replaced by non-hydrogen groups. The number of substituents is not limited, as long as they can be obtained through chemical reactions. It is not limited to a specific position, as long as the hydrogen at the position can be replaced by a substituent. For example, carbazolyl includes any of the following groups, but is not limited thereto, as long as it is not otherwise described in this specification,

[0081]

[0082] Indicates the position of substitution. "Unsubstituted" means that hydrogen atoms remain, in this case, hydrogen atoms include protium, deuterium, tritium.

[0083] When two or more substituents are present, the two or more substituents may be the same or different.

[0084] As used herein, the term "phenylene naphthyl" refers to

[0085] As used herein, the term "phenylnaphthyl" includes

[0086] Refers to the replacement position.

[0087] As used in the present invention, hydrogen atoms include protium, deuterium and tritium. The compounds of the present invention may contain deuterium atoms of natural origin, or may introduce deuterium atoms by deuterating a portion or all of the raw material compounds. If deuterium atoms are introduced from the raw materials, the deuteration rate may be 100%, or may be less than 100%, or less than 95%, or less than 90%, or less than 80%, and the deuteration rate may also be more than 1%, or more than 5%, or more than 10%. If the deuteration rate is not 100%, it means a mixture of deuterated compounds and undeuterated compounds, or a mixture of completely deuterated compounds and incompletely deuterated compounds, or a mixture of completely deuterated compounds and undeuterated compounds and incompletely deuterated compounds.

[0088] As used in the present invention, terms such as first, second, A, B, etc. are used. The above terms are only used to distinguish components, and do not limit the nature or order of the components to which the terms correspond.

[0089] In one specific embodiment of the present invention, in formula (1), X 1 Selected from O, S, N, NR, X 2 Selected from O, S, N, NR, One of them is a single bond and the other is a double bond;

[0090] R is selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloadamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted indenyl, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted substituted or unsubstituted pyridyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazine, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted furanyl, substituted or unsubstituted substituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl;

[0091] L 1 is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted phenylene naphthylene, a substituted or unsubstituted binaphthylene, a substituted or unsubstituted fluoranthenylene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted perylene, a substituted or unsubstituted pyrenylene, a substituted or unsubstituted benzopyrenylene, a substituted or unsubstituted ... substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted pyridinylene,

[0092] R 1 is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloadamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted indenyl, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted substituted or unsubstituted pyridyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazine, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted furanyl, substituted or unsubstituted substituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl;

[0093] The substituted or unsubstituted substituents are each independently selected from a combination of one or more of deuterium, halogen, cyano, C1-C10 alkyl, C6-C30 aryl, and C3-C30 heteroaryl;

[0094] L 2 -L 6 Select from the linking keys;

[0095] R 2 -R 6 Selected from hydrogen.

[0096] Preferably, the substituted or unsubstituted substituents are each independently selected from one or more combinations of deuterium, halogen, cyano, phenyl, naphthyl, anthracenyl, phenanthryl, phenyl-substituted anthracenyl, pyrene, triphenylene, fluoranthene, dibenzofuranyl, dibenzothiophenyl, and carbazolyl;

[0097] Preferably, formula (1) is selected from formula (1-1), X 1 Selected from NR;

[0098] Preferably, formula (1) is selected from formula (1-2), X 1 Selected from NR, O or S.

[0099] In one specific embodiment of the present invention, in formula (1), X 1 Selected from O, S, N, NR, X 2 Selected from O, S, N, NR, One of them is a single bond and the other is a double bond;

[0100] R is selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloadamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted indenyl, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted substituted or unsubstituted pyridyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazine, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted furanyl, substituted or unsubstituted substituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl;

[0101] L 1 is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted phenylene naphthylene, a substituted or unsubstituted binaphthylene, a substituted or unsubstituted fluoranthenylene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted perylene, a substituted or unsubstituted pyrenylene, a substituted or unsubstituted benzopyrenylene, a substituted or unsubstituted ... substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted pyridinylene,

[0102] R 1is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloadamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted indenyl, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted substituted or unsubstituted pyridyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazine, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted furanyl, substituted or unsubstituted substituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl;

[0103] L 2 is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted phenylene naphthylene, a substituted or unsubstituted binaphthylene, a substituted or unsubstituted fluoranthenylene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted perylene, a substituted or unsubstituted pyrenylene, a substituted or unsubstituted benzopyrenylene, a substituted or unsubstituted ... substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted pyridinylene,

[0104] R 2is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloadamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted indenyl, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted substituted or unsubstituted pyridyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazine, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted furanyl, substituted or unsubstituted substituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl;

[0105] The substituted or unsubstituted substituents are each independently selected from a combination of one or more of deuterium, halogen, cyano, C1-C10 alkyl, C6-C30 aryl, and C3-C30 heteroaryl;

[0106] L 3 -L 6 Select from the linking keys;

[0107] R 3 -R 6 Selected from hydrogen.

[0108] Preferably, the substituted or unsubstituted substituents are each independently selected from one or more combinations of deuterium, halogen, cyano, phenyl, naphthyl, anthracenyl, phenanthryl, phenyl-substituted anthracenyl, pyrene, triphenylene, fluoranthene, dibenzofuranyl, dibenzothiophenyl, and carbazolyl;

[0109] Preferably, formula (1) is selected from formula (1-1), X 1 Selected from NR;

[0110] Preferably, formula (1) is selected from formula (1-2), X 1 Selected from NR, O or S.

[0111] In one specific embodiment of the present invention, in formula (1), X 1 Selected from O, S, N, NR, X 2 Selected from O, S, N, NR, One of them is a single bond and the other is a double bond;

[0112] R is selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloadamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted indenyl, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted substituted or unsubstituted pyridyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazine, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted furanyl, substituted or unsubstituted substituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl;

[0113] L 1 is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted phenylene naphthylene, a substituted or unsubstituted binaphthylene, a substituted or unsubstituted fluoranthenylene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted perylene, a substituted or unsubstituted pyrenylene, a substituted or unsubstituted benzopyrenylene, a substituted or unsubstituted ... substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted pyridinylene,

[0114] R 1 is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloadamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted indenyl, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted substituted or unsubstituted pyridyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazine, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted furanyl, substituted or unsubstituted substituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl;

[0115] L 3 is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted phenylene naphthylene, a substituted or unsubstituted binaphthylene, a substituted or unsubstituted fluoranthenylene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted perylene, a substituted or unsubstituted pyrenylene, a substituted or unsubstituted benzopyrenylene, a substituted or unsubstituted ... substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted pyridinylene,

[0116] R 3is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloadamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted indenyl, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted substituted or unsubstituted pyridyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazine, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted furanyl, substituted or unsubstituted substituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl;

[0117] The substituted or unsubstituted substituents are each independently selected from a combination of one or more of deuterium, halogen, cyano, C1-C10 alkyl, C6-C30 aryl, and C3-C30 heteroaryl;

[0118] L 2 , L 4 -L 6 Select from the linking keys;

[0119] R 2 , R 4 -R 6 Selected from hydrogen.

[0120] Preferably, the substituted or unsubstituted substituents are each independently selected from one or more combinations of deuterium, halogen, cyano, phenyl, naphthyl, anthracenyl, phenanthryl, phenyl-substituted anthracenyl, pyrene, triphenylene, fluoranthene, dibenzofuranyl, dibenzothiophenyl, and carbazolyl;

[0121] Preferably, formula (1) is selected from formula (1-1), X 1 Selected from NR;

[0122] Preferably, formula (1) is selected from formula (1-2), X 1 Selected from NR, O or S.

[0123] In one specific embodiment of the present invention, in formula (1), X 1 Selected from O, S, N, NR, X 2 Selected from O, S, N, NR, One of them is a single bond and the other is a double bond;

[0124] R is selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloadamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted indenyl, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted substituted or unsubstituted pyridyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazine, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted furanyl, substituted or unsubstituted substituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl;

[0125] L 1 is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted phenylene naphthylene, a substituted or unsubstituted binaphthylene, a substituted or unsubstituted fluoranthenylene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted perylene, a substituted or unsubstituted pyrenylene, a substituted or unsubstituted benzopyrenylene, a substituted or unsubstituted ... substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted pyridinylene,

[0126] R 1 is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloadamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted indenyl, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted substituted or unsubstituted pyridyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazine, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted furanyl, substituted or unsubstituted substituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl;

[0127] L 5 is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted phenylene naphthylene, a substituted or unsubstituted binaphthylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted fluoranthenylene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted perylene, a substituted or unsubstituted pyrenylene, a substituted or unsubstituted benzopyrenylene, a substituted or unsubstituted ... substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted pyridinylene,

[0128] R 5is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloadamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted indenyl, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted substituted or unsubstituted pyridyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazine, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted furanyl, substituted or unsubstituted substituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl;

[0129] The substituted or unsubstituted substituents are each independently selected from a combination of one or more of deuterium, halogen, cyano, C1-C10 alkyl, C6-C30 aryl, and C3-C30 heteroaryl;

[0130] L 2 -L 4 , L 6 Select from the linking keys;

[0131] R 2 -R 4 , R 6 Selected from hydrogen.

[0132] Preferably, the substituted or unsubstituted substituents are each independently selected from one or more combinations of deuterium, halogen, cyano, phenyl, naphthyl, anthracenyl, phenanthryl, phenyl-substituted anthracenyl, pyrene, triphenylene, fluoranthene, dibenzofuranyl, dibenzothiophenyl, and carbazolyl;

[0133] Preferably, formula (1) is selected from formula (1-1), X 1 Selected from NR;

[0134] Preferably, formula (1) is selected from formula (1-2), X 1 Selected from NR, O or S.

[0135] In one embodiment of the present invention, the heterocyclic compound is selected from any one of the following compounds No. 1 to 336:

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158] Organic electroluminescent element

[0159] The structure of the organic electroluminescent element of the present invention is a disclosed structure, comprising an anode, a cathode and an organic layer located between the anode and the cathode, wherein the organic layer comprises a light-emitting layer, and at least one layer of the organic layer comprises the compound of the present invention.

[0160] The organic layer may further include one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer, but is not limited thereto.

[0161] The light-emitting element of the present invention may emit fluorescence or phosphorescence or a combination thereof. The light-emitting element may emit light alone or in series with multiple light-emitting units.

[0162] As simple light emitting elements, the following may be cited, but are not limited thereto:

[0163] (1) hole transport layer / fluorescent light emitting layer / electron transport layer;

[0164] (2) hole transport layer / phosphorescent light emitting layer / electron transport layer;

[0165] (3) hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / electron transport layer;

[0166] (4) hole transport layer / first phosphorescent light-emitting layer / second phosphorescent light-emitting layer / electron transport layer;

[0167] (5) hole transport layer / fluorescent emitting layer / spacer layer / phosphorescent emitting layer / electron transport layer;

[0168] (6) hole transport layer / electron blocking layer / fluorescent light emitting layer / electron transport layer;

[0169] (7) hole transport layer / electron blocking layer / fluorescent light emitting layer / hole blocking layer / electron transport layer;

[0170] (8) hole transport layer / electron blocking layer / phosphorescent light emitting layer / electron transport layer;

[0171] (9) hole transport layer / electron blocking layer / phosphorescent emitting layer / hole blocking layer / electron transport layer;

[0172] (10) hole injection layer / hole transport layer / phosphorescent light emitting layer / electron transport layer / electron injection layer;

[0173] (11) hole injection layer / hole transport layer / fluorescent light emitting layer / electron transport layer / electron injection layer;

[0174] (12) hole injection layer / hole transport layer / electron blocking layer / phosphorescent light emitting layer / electron transport layer / electron injection layer;

[0175] (13) hole injection layer / hole transport layer / electron blocking layer / fluorescent light emitting layer / electron transport layer / electron injection layer;

[0176] The phosphorescent / fluorescent light-emitting layers mentioned above can each emit light of a different color.

[0177] As a tandem type organic electroluminescent element, it can be an anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode. The intermediate layer can also be generally called a charge generation layer, an electron extraction layer, a connecting layer, etc. For example, when stacking a fluorescent light-emitting layer and a phosphorescent light-emitting layer, an intermediate layer is placed between the fluorescent light-emitting layer and the phosphorescent light-emitting layer in order to prevent the excitons generated by the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer or to adjust the balance of carriers.

[0178] When the organic light emitting element includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0179] The organic electroluminescent element of the present specification can be manufactured by using materials and methods known in the art, except that one or more of the organic layers is prepared by using a compound comprising Formula I.

[0180] As the anode material, a material having a relatively large work function can be used, and transparent conductive oxides, metals, conductive polymers, etc. can be used. Specific examples of the anode material include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO; 2 : Sb; conductive polymer, such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (poly [3,4- (ethylene-1,2-dioxy) thiophene], PEDOT), polypyrrole and polyaniline, etc., but not limited thereto.

[0181] As the cathode material, a material with a low work function is generally used to facilitate electron injection into the organic layer, and metals, metal oxides, conductive polymers, etc. can be used. Specific examples of cathode materials include: metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials, such as LiF / Al or LiO 2 / Al, etc., but not limited to these.

[0182] The hole injection layer is a layer that injects holes from the electrode and has the ability to transport holes. In order to reduce the energy level difference between the electrodes, the hole injection layer is mainly prepared based on aromatic amine compounds, and can also be prepared using the following materials, such as copper phthalocyanine in the metal complex, and HATCN (2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene) with a phenylene structure in the material with the lowest unoccupied molecular orbital energy level. When used as a light-emitting host and dopant, F4-TCNQ (2 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone) inducer with the lowest unoccupied molecular orbital energy level can be doped in the aromatic amine compound.

[0183] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material can appropriately receive holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Aromatic amine derivatives, triphenyldiamine derivatives, etc. can be used, and low molecular or high molecular materials can also be used.

[0184] The luminescent material is a material that receives holes and electrons from the hole transport layer and the electron transport layer, respectively, and combines the holes and electrons to emit light in the visible light region. The luminescent layer material includes a host material and a doping material. Red, green or blue luminescent materials can be used, and two or more luminescent materials can be mixed as needed. As the luminescent material, a fluorescent material can be used, and a phosphorescent material can also be used. As the luminescent material, a single component material can be used, and a multi-component material can also be used.

[0185] The electron transport layer receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and the electron transport material can receive electrons from the cathode and transfer the electrons to the light-emitting layer. The metal complexes of triazine derivatives, oxadiazole derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, fluorenone derivatives, diphenyl dicyanoethylene and its derivatives, 8-hydroxyquinoline and its derivatives, etc. can be used, and polymer materials and small molecule materials can also be used.

[0186] The electron injection layer is a layer that injects electrons from the electrode. The present application uses LiF, however, the present application is not limited thereto.

[0187] The hole blocking layer is a layer that blocks holes from reaching the cathode.

[0188] The electron blocking layer is a layer that blocks electrons from reaching the anode.

[0189] The organic light-emitting element of the present specification may be a top-emitting element, a bottom-emitting element, or a dual-emission element according to the materials used.

[0190] The charge generation layer is an intermediate layer between the anode and cathode in a tandem structure element, and is a layer that generates holes and electrons by charge separation. The charge generation layer is usually formed by a P-type layer on the cathode side and an N-type layer on the anode side, and can effectively separate charges and effectively transport carriers.

[0191] Those skilled in the art can synthesize the compounds of the present invention by referring to the synthesis of the following compounds and known synthesis methods.

[0192] Those skilled in the art can synthesize the compounds of the present invention by referring to the synthesis of the following compounds and known synthesis methods. There are many synthesis methods for the compounds of the present invention, and the following methods are only illustrative.

[0193] Synthesis formula: The following general formula is only one method for synthesizing the compounds of the present invention. The compounds of the present invention can also be synthesized by other methods.

[0194]

[0195] The same synthesis method can be used for different substitution positions. 1 , X 2 , L 1 -L 6 , R, R 1 -R 6 With X in formula (1) 1 , X 2 , L 1 -L 6 , R, R 1 -R 6 The meaning expressed is the same.

[0196] Synthesis Example 1 Synthesis of Compound No. 4

[0197] 1. Synthesis of intermediate 4-1

[0198]

[0199] N 2 Under the atmosphere, 2,5-dichlorobenzoxazole (11 g, 58.9 mmol), compound A (25 g, 61.9 mmol), potassium carbonate (16.3 g, 117.7 mmol), tetrakis(triphenylphosphine)palladium (1.36 g, 1.2 mmol) and a mixture of 120 mL of tetrahydrofuran and 40 mL of water were heated to 80°C for reaction. After the reaction was completed, the reaction solution was cooled to room temperature and filtered to obtain a light yellow intermediate 4-1 (23.2 g, yield 92%).

[0200] LC-MS (APCI) (M+H) + :430.28.

[0201] 2. Synthesis of intermediate 4-2

[0202]

[0203] Under nitrogen atmosphere, the mixture of intermediate 4-1 (23 g, 53.6 mmol), o-formylphenylboronic acid (8.5 g, 56.3 mmol), bistriphenylphosphine palladium dichloride (0.78 g, 1.1 mmol), potassium carbonate (14.8 g, 107.2 mmol), 120 mL tetrahydrofuran and 40 mL water was heated to 80°C for reaction. After the reaction was completed, the reaction solution was cooled to room temperature and filtered to obtain a light yellow intermediate 4-2 (22 g, yield 82%).

[0204] LC-MS (APCI) (M+H) + :500.43.

[0205] 3. Synthesis of compound 4

[0206]

[0207] Add intermediate 4-2 (22g, 44.1mmol) and trifluoroacetic acid 200mL to the reaction bottle, slowly add trimethylsilane (10.2g, 88.2mmol) at room temperature, stir at room temperature for 30min after the addition is complete, slowly add trifluoromethanesulfonic acid (39.7g, 264.5mmol), and then raise the temperature to 75°C after the addition is complete, and react for 1 hour. After the reaction is completed, the reaction solution is extracted with dichloromethane, and the solvent is removed after drying with anhydrous sodium sulfate. Purification is performed by silica gel chromatography (developing solvent volume ratio: DCM:THF=30:1) to obtain a light yellow compound 4 (11g, yield 50%).

[0208] LC-MS (APCI) (M+H) + :497.38.

[0209] 1 H NMR(400MHz,Methylene Chloride-d2)δ8.50(d,2H),8.34–8.20(m,4H),8.18–8.03(m,5H),7.98(d,1H),7.91–7.76(m,4H),7.73(td,1H),7.68–7.58(m,2H),7.52(td,1H).

[0210] Synthesis Example 2 Synthesis of Compound No. 25

[0211] 1. Synthesis of Intermediate 25-1

[0212]

[0213] N 2 Under the atmosphere, compound B (11.6 g, 27.0 mmol) and 2,5-dichlorobenzoxazole (5.6 g, 29.9 mmol) were dissolved in 150 mL of tetrahydrofuran, and potassium carbonate (7.5 g, 54.3 mmol), bis(triphenylphosphine)palladium dichloride (0.5 g, 0.7 mmol), and 50 mL of water were added, and the temperature was raised to 75°C for reaction. After the reaction was completed, the temperature was lowered to room temperature, and intermediate 25-1 (11 g, yield 90%) was obtained after filtration.

[0214] LC-MS (APCI) (M+H) + :456.41.

[0215] 2. Synthesis of Intermediate 25-2

[0216]

[0217] N 2 Under the atmosphere, the intermediate 25-1 (18g, 39.6mmol), 2-formylphenylboronic acid (18g, 120mmol), sodium tert-butoxide (15g, 156.1mmol), dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (II) (0.6g, 0.8mmol) were added to a four-necked reaction bottle, and then a mixture of 300mL toluene, 120mL ethanol, and 120mL water was added, and the temperature was raised to reflux for reaction. After the reaction was completed, the mixture was cooled to room temperature and separated. The organic phase was dried over anhydrous sodium sulfate and column chromatography (n-hexane: dichloromethane volume ratio 20:1) was used to obtain the intermediate 25-2 (14g, yield 67%).

[0218] LC-MS (APCI) (M+H) + :526.45.

[0219] 3. Synthesis of Compound 25

[0220]

[0221] N 2 Under atmosphere, intermediate 25-2 (14 g, 27.7 mmol) was dissolved in 200 mL of trifluoroacetic acid, and 9 mL of trimethylsilyl azide was added dropwise at room temperature. After the addition was complete, the mixture was stirred at room temperature for 5 min, and then 13.7 mL of trifluoromethanesulfonic acid was added dropwise. After the addition was complete, the temperature was raised to 60°C. After the reaction was completed, the reaction solution was slowly added to ice water, and then extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, and then purified by column chromatography (n-hexane: dichloromethane volume ratio 20:1), and then slurried with toluene to obtain compound 25 (4 g, yield 29%).

[0222] LC-MS (APCI) (M+H) + :523.40.

[0223] 1 H NMR(400MHz,Methylene Chloride-d 2 )δ9.77–9.71(d,1H),8.84–8.76(t,2H),8.57–8.55(d,1H),8.01(s,1H),7.85–7.84(d,1H),7.77–7.75(d,2H),7.75(s, 1H),7.68–7.65(d,2H),7.62–7.60(m,2H),7.60–7.54(m,3H),7.54–7.51(m,1H),7.48–7.42(m,2H),7.31–7.25(m,3H).

[0224] Synthesis Example 3 Synthesis of Compound No. 45

[0225] 1. Synthesis of Intermediate 45-1

[0226]

[0227] In a 500mL four-necked flask, 2-phenylbenzo[d]oxazol-4-amine (20 g, 95.2 mmol), 200 mL of dichloromethane, and triethylamine (39.6 mL, 285.4 mmol) were added in sequence and stirred at room temperature for 30 minutes. Then, o-bromobenzoyl chloride (13 mL, 99.9 mmol) was added dropwise to the system and stirred at room temperature for 2 hours. After the reaction was completed, water was added for washing, and the organic phase was separated and concentrated and purified by pulping to obtain intermediate 45-1 (33.94 g, yield 91%).

[0228] LC-MS (APCI) (M+H) + :=393.23.

[0229] 2. Synthesis of Intermediate 45-2

[0230]

[0231] Under nitrogen atmosphere, intermediate 45-1 (33.94 g, 86.5 mmol), palladium acetate (390 mg, 1.7 mmol), potassium carbonate (23.85 g, 172.6 mmol), and 400 mL of N,N-dimethylformamide were added to a 1L single-mouth bottle and reacted at 150°C for 2 hours. After the reaction was completed, the system was concentrated, water and dichloromethane were added to extract the liquid, the organic phase was concentrated and combined, and separated by column chromatography (n-hexane: dichloromethane = 1:2) to obtain intermediate 45-2 (16.1 g, yield 60%).

[0232] LC-MS (APCI) (M+H) + :313.21.

[0233] 3. Synthesis of intermediate 45-3

[0234]

[0235] Into a 500mL four-necked bottle, add intermediate 45-2 (16.1g, 51.6mmol) and 200mL of phosphorus oxychloride, and reflux for 3 hours. After the reaction is completed, concentrate the system, dissolve in ethyl acetate and slowly pour into ice water, adjust the pH to neutral, extract with ethyl acetate several times, separate by column chromatography (n-hexane: dichloromethane volume ratio = 1:1), and obtain intermediate 45-3 (12.1g, yield 70%).

[0236] LC-MS (APCI) (M+H) + :331.19.

[0237] 4. Synthesis of Compound 45

[0238]

[0239] Under nitrogen atmosphere, intermediate 45-3 (12.1 g, 36.3 mmol), compound B (17.37 g, 40.4 mmol), tetrahydrofuran 300 mL, 100 mL, potassium carbonate (10.14 g, 73.4 mmol), tetrakis (triphenylphosphine) palladium (850 mg, 0.7 mmol) were added to a 1L four-necked bottle in sequence, and refluxed for 3 hours. After the reaction was completed, water was separated, the organic phase was concentrated, and the mixture was separated by column chromatography (n-hexane: dichloromethane volume ratio = 1:1) to obtain compound 45 (20.8 g, yield 95%).

[0240] LC-MS (APCI) (M+H) + :599.53.

[0241] 1 H NMR(400MHz,Methylene Chloride-d2)δ8.79(dd,3H),8.70(d,1H),8.33(dd,2H),8.05–7.32(m,18H),7.27–7.17(m,2H).

[0242] Synthesis Example 4 Synthesis of Compound No. 88

[0243] 1. Synthesis of intermediate 88-1

[0244]

[0245] N 2 Under atmosphere, compound C (24 g, 74.7 mmol), 2-chloro-6-bromobenzaldehyde (15.58 g, 71 mmol), bis(triphenylphosphine)palladium dichloride (1.05 g, 1.5 mmol), K 2 CO 3 (15.49 g, 112.1 mmol) was placed in a four-necked reaction bottle, and 300 mL of tetrahydrofuran and 100 mL of water were added. The mixture was heated to reflux for 4 h, cooled to room temperature, filtered, and the filtrate was concentrated and 200 mL of ethanol was added to slurry to obtain intermediate 88-1 (23.8 g, yield 95%).

[0246] LC-MS (APCI) (M+H) + :336.79.

[0247] 2. Synthesis of Intermediate 88-2

[0248]

[0249] N 2 Under the atmosphere, the intermediate 88-1 (23.8 g, 70.9 mmol) was added to 1L four-necked flask, 300 mL of acetic acid was added, and trimethylsilyl azide (16.32 g, 141.7 mmol) and trifluoromethanesulfonic acid (31.9 g, 212.6 mmol) were added, and then heated to reflux and reacted for 3 h. After the reaction was completed, the mixture was concentrated and separated by column chromatography (n-hexane: dichloromethane volume ratio = 1:1), and then slurried with 100 mL of ethanol to obtain the intermediate 88-2 (12 g, yield 51%).

[0250] LC-MS: [M+H] + =331.77.

[0251] 3. Synthesis of Compound 88

[0252]

[0253] N 2 Under atmosphere, intermediate 88-2 (10.68 g, 32.3 mmol), compound B (16.39 g, 38.1 mmol), bis(di-tert-butyl-4-dimethylaminophosphine)palladium chloride (0.26 g, 0.36 mmol), K 2 CO 3 (7.51 g, 54.4 mmol) was placed in a 1L four-necked reaction bottle, and 300 mL of tetrahydrofuran and 100 mL of water were added. The mixture was heated to reflux for 5 h, cooled to room temperature, separated and concentrated, and then slurried with 100 mL of ethyl acetate three times to obtain compound 88 (11 g, yield 57%).

[0254] LC-MS (APCI) (M+H) + :599.71.

[0255] 1 H NMR(400MHz,Methylene Chloride-d2)δ8.80–8.70(m,2H),8.24–8.18(m,2H),7.97(t,1H),7.90–7.82(m,2H),7.79–7.72( m,1H),7.70–7.65(m,3H),7.65–7.55(m,7H),7.51–7.45(m,4H),7.44–7.32(m,3H),7.24(ddt,1H).

[0256] Synthesis Example 5 Synthesis of Compound No. 107

[0257] 1. Synthesis of intermediate 107-1

[0258]

[0259] N 2 Under the atmosphere, 2-amino-4-chlorophenol (20 g, 139.3 mmol) was added to a four-necked reaction bottle, and then 1,4-dioxane (400 mL in total) was added, and benzoyl chloride (21.54 g, 153.2 mmol) was added dropwise and the temperature was raised to reflux for reaction for 1 h. After the reaction was complete, the reaction solution was cooled to room temperature, filtered and concentrated, and 100 mL of methanol was added for slurrying to obtain intermediate 107-1 (25.6 g, yield 80%).

[0260] LC-MS (APCI) (M+H) + :230.66.

[0261] 2. Synthesis of Intermediate 107-2

[0262]

[0263]

[0264] N 2 Under the atmosphere, intermediate 107-1 (25.6 g, 111.5 mmol), potassium acetate (32.82 g, 334.4 mmol), biboric acid pinacol ester (36.8 g, 144.9 mmol), 1,1-bis(diphenylphosphine)diphosphine iron palladium dichloride (1.63 g, 2.2 mmol) were added to a four-necked reaction bottle, and 600 mL of anhydrous 1,4-dioxane was added. The temperature was raised to strong reflux reaction for 12 h, and the reaction solution was cooled and concentrated by suction. The intermediate 107-2 (24 g, yield 67%) was obtained by slurrying with 100 mL of n-hexane.

[0265] LC-MS (APCI) (M+H) + :322.18.

[0266] 3. Synthesis of Intermediate 107-3

[0267]

[0268] N 2 Under atmosphere, intermediate 107-2 (24 g, 74.72 mmol), 2-bromo-4-chlorobenzaldehyde (15.58 g, 70.99 mmol), bis(triphenylphosphine)palladium dichloride (1.05 g, 1.5 mmol), K 2 CO 3 (15.49 g, 112.09 mmol) was placed in a four-necked reaction bottle, and 300 mL of tetrahydrofuran and 100 mL of water were added. The reaction was heated to reflux for 4 h, cooled to room temperature, and the filtrate was concentrated by suction. 200 mL of ethanol was added for slurrying to obtain intermediate 107-3 (22.58 g, yield 90%).

[0269] LC-MS (APCI) (M+H) + :336.79.

[0270] 4. Synthesis of Intermediate 107-4

[0271]

[0272] N 2 Under the atmosphere, the intermediate 107-3 (22.58 g, 67.25 mmol) was added to 300 mL of acetic acid in a 1L four-necked flask, and trimethylsilyl azide (15.49 g, 134.49 mmol) and trifluoromethanesulfonic acid (30.27 g, 201.74 mmol) were added, and then heated to reflux for 3 h. After the reaction was completed, the mixture was concentrated and eluted by column chromatography (n-hexane: dichloromethane volume ratio = 1:1), and then slurried with 100 mL of ethanol to obtain the intermediate 107-4 (10.68 g, yield 48%).

[0273] LC-MS (APCI) (M+H) + :331.77.

[0274] 5. Synthesis of Intermediate 107-2

[0275]

[0276] N 2Under atmosphere, intermediate 107-4 (10.68 g, 32.29 mmol), compound B (14.59 g, 33.90 mmol), bis(di-tert-butyl-4-dimethylaminophosphine)palladium chloride (0.229 g, 0.322 mmol), K 2 CO 3 (6.69 g, 48.43 mmol) was placed in a 1L four-necked reaction bottle, and 300 mL of tetrahydrofuran and 100 mL of water were added, and the mixture was heated to reflux for 5 h, cooled to room temperature, separated from the water, concentrated, and recrystallized from 100 mL of dichloroethane to obtain compound 107 (9.67 g, yield 50%).

[0277] LC-MS (APCI) (M+H) + :599.71.

[0278] 1 H NMR(400MHz,Methylene Chloride-d2)δ8.23–8.18(m,5H),7.83(dd,2H),7.69–7.63(m,5H),7.53(d,2H),7.52–7.46(m,9H),7.45(d,1H),7.41(d,1H),7.39(d,1H).

[0279] Synthesis Example 6 Synthesis of Compound No. 187

[0280] 1. Synthesis of Intermediate 187-1

[0281]

[0282] N 2 Under the atmosphere, 5-bromo-2-phenylbenzimidazole (60.0 g, 220 mmol), p-chloroiodobenzene (52.0 g, 220 mmol), potassium carbonate (60.6 g, 440 mmol), 1,10-phenanthroline (4.0 g, 22 mmol) and cuprous iodide (0.84 g, 4.4 mmol) were added to 600 mL of anhydrous dimethyl sulfoxide solution, and the temperature was raised to 120°C for reaction. After the reaction was completed (about 10 h), the reaction solution was cooled to room temperature, poured into 1 L of water, washed and filtered, and the filter cake was eluted by column chromatography (n-hexane: dichloromethane volume ratio = 2:1) to obtain intermediate 187-1 (27.0 g, yield 32%).

[0283] LC-MS (APCI) (M+H) + :383.1.

[0284] 2. Synthesis of intermediate 187-2

[0285]

[0286] N 2 Under the atmosphere, intermediate 187-1 (27.0 g, 70.7 mmol), (2-formylphenyl)boric acid (12.4 g, 82.7 mmol), potassium carbonate (19.5 g, 141 mmol), bistriphenylphosphine palladium dichloride (0.52 g, 0.74 mmol) were added to a mixture of 210 mL of tetrahydrofuran and 70 mL of water, and heated to 70°C for 7 h. The reaction solution was cooled to room temperature and ethyl acetate was added. After extraction, the organic phase was spin-dried and subjected to column chromatography (eluted with dichloromethane) to obtain intermediate 187-2 (27.0 g, yield 94%).

[0287] LC-MS (APCI) (M+H) + :409.89.

[0288] 3. Synthesis of intermediate 187-3

[0289]

[0290] Trifluoroacetic acid (270 mL) was slowly added to the intermediate 187-2 (27.0 g, 66.5 mmol), and then trimethylsilyl azide (19.15 g, 166.5 mmol) and trifluoromethanesulfonic acid (19.5 g, 130 mmol) were slowly added dropwise at room temperature. After the addition was complete, the temperature was raised to 65°C and the reaction was continued for 3 hours. The reaction solution was cooled to room temperature and quenched in ice water, and ethyl acetate was added for extraction. The organic phase was spin-dried and then subjected to column chromatography (n-hexane: dichloromethane volume ratio = 1:1) to obtain the intermediate 187-3 (13 g, yield 48%).

[0291] LC-MS (APCI) (M+H) + :405.89.

[0292] 4. Synthesis of Compound 187

[0293]

[0294] Under nitrogen atmosphere, compound D (6.23 g, 18.97 mmol), intermediate 187-3 (7 g, 17.2 mmol), tetrakis(triphenylphosphine)palladium (0.2 g, 0.17 mmol), potassium carbonate (4.76 g, 34.50 mmol) were added to a mixed solution of 52.5 mL of tetrahydrofuran and 17.5 mL of water, and the mixture was heated to 65°C for 5 h. The reaction solution was cooled to room temperature, extracted with ethyl acetate, and the organic phase was spin-dried and subjected to column chromatography (eluted with dichloromethane) to obtain a white compound 187 (7.87 g, yield 80%).

[0295] LC-MS (APCI) (M+H) + :572.46.

[0296] 1 H NMR(400MHz,Methylene Chloride-d2)δ8.23(d,1H),8.20–8.13(m,3H),8.08(s,2H),8.07–7.92(m,4H),7.74 (dd,3H),7.72–7.66(m,2H),7.65–7.57(m,2H),7.56–7.46(m,4H),7.45–7.32(m,4H).

[0297] Synthesis Example 7 Synthesis of Compound No. 31

[0298]

[0299] Under nitrogen environment, intermediate 32-4 (10 g, 26.26 mmol), 6-chloroboric acid (7.5 g, 27.57 mmol), tetrakis(triphenylphosphine)palladium (0.6 g, 0.5 mmol), potassium carbonate (10.6 g, 73.8 mmol), 75 mL of tetrahydrofuran and 25 mL of water were added to a four-necked bottle in sequence. The mixture was heated to reflux for 2 h, cooled to room temperature, filtered, and the filtrate was concentrated under reduced pressure and slurried with 100 mL of toluene to obtain compound 31 (12 g, yield 80%).

[0300] LC-MS (APCI) (M+H) + :573.19.

[0301] Synthesis Example 8 Synthesis of Compound No. 32

[0302] 1. Synthesis of Intermediate 32-1

[0303]

[0304] Under nitrogen atmosphere, 4-chloro-1-naphthoic acid (25.0 g, 121.36 mmol) was placed in a 500 mL single-mouth bottle, 3 mL of N, N-dimethylformamide and 125 mL of thionyl chloride were added, and the mixture was heated to 150°C and stirred for 6 h. After the reaction was completed, the reaction solution was concentrated to obtain intermediate 32-1 (27.3 g, yield 100%).

[0305] LC-MS (APCI) (M+H) + :225.07.

[0306] 2. Synthesis of intermediate 32-2

[0307]

[0308] Under nitrogen atmosphere, intermediate 32-1 (31.2 g, 138.66 mmol) was placed in a four-necked bottle, 150 mL of 1,4-dioxane was added to dissolve, and stirred for 3 min. 2-amino-4-bromophenol (26.1 g, 138.66 mmol) dissolved in 100 mL of 1,4-dioxane was slowly added dropwise, and the reaction was stirred for 1 h. The temperature was raised to 110 ° C, 29 mL of trifluoromethanesulfonic acid was slowly added dropwise, and the mixture was stirred for 2 h. After the reaction was completed, the reaction solution was cooled to room temperature, extracted with dichloromethane, and column chromatography (n-hexane: ethyl acetate volume ratio = 2: 1) was used to obtain intermediate 32-2 (23.1 g, yield 47%).

[0309] LC-MS (APCI) (M+H) + :360.13.

[0310] 3. Synthesis of intermediate 32-3

[0311]

[0312] Under nitrogen atmosphere, intermediate 32-2 (23.1 g, 64.17 mmol), (2-formylphenyl) boronic acid (10.1 g, 67.37 mmol), tetrakistriphenylphosphine palladium (1.5 g, 1.28 mmol) and potassium carbonate (26.5 g, 192.51 mmol) were added to a mixed solution of 350 mL of toluene, 150 mL of ethanol and 150 mL of water, and the mixture was heated to reflux for 4 hours. After the reaction was completed, the reaction solution was cooled to room temperature, extracted with dichloromethane, and column chromatography (n-hexane: ethyl acetate volume ratio = 1:1) was used to obtain intermediate 32-3 (17.4 g, yield 71%).

[0313] LC-MS (APCI) (M+H) + :384.26.

[0314] 4. Synthesis of intermediate 32-4

[0315]

[0316] Under nitrogen atmosphere, intermediate 32-3 (17.4 g, 45.40 mmol) was placed in a four-necked bottle, 310 mL of trifluoroacetic acid was added, and the mixture was stirred for 5 min. 23 mL of azidotrimethylsilane was added, and 33 mL of trifluoromethanesulfonic acid was added after stirring for 5 min. When the system was stable, the temperature was raised to 100 ° C, and the mixture was stirred for 4 h. After the reaction was completed, the heating was stopped, and the reaction solution was poured into ice water. The product was precipitated and filtered, and intermediate 32-4 (8.2 g, yield 48%) was obtained by column chromatography (n-hexane: dichloromethane volume ratio = 1:1).

[0317] LC-MS (APCI) (M+H) + :381.25.

[0318] 5. Synthesis of compound 32

[0319]

[0320] Under nitrogen atmosphere, 150 mL of anhydrous tetrahydrofuran and 1-(4-bromophenyl)-2-phenyl-1H-benzo[d]imidazole (7.39 g, 22.07 mmol) were added to a four-necked bottle, stirred for 10 min, then cooled to -78°C, n-butyl lithium (9 mL, 22.07 mmol) was slowly added dropwise, stirred at -78°C for 15 min, and then intermediate 32-4 (8.39 g, 22.07 mmol) was added, and after the addition was complete, the temperature was raised to room temperature and reacted for 60 min. After the reaction was completed, the reaction solution was cooled to room temperature, extracted with dichloromethane, and column chromatography (n-hexane: dichloromethane volume ratio = 1:4) was used to obtain compound 32 (12 g, yield 89%).

[0321] LC-MS (APCI) (M+H) + :615.46.

[0322] 1 H NMR(400MHz,Methylene Chloride-d2)δ9.69(dt,1H),8.58(d,1H),8.10–8.02(m,2H),7.88–7.76(m,4H),7.74–7.62(m,9H),7.55–7.49(m,3H),7.45–7.33(m,6H).

[0323] Synthesis Example 9 Synthesis of Compound No. 163

[0324] 1. Synthesis of intermediate 163-1

[0325]

[0326] Under nitrogen atmosphere, compound E (10.0 g, 17.81 mmol), 2,5-dichlorobenzo[d]oxazole (3.4 g, 17.81 mmol), potassium carbonate (4.9 g, 35.62 mmol) and dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (II) (0.25 g, 0.36 mmol) were placed in a four-necked bottle, 100 mL of tetrahydrofuran and 33 mL of deionized water were added, and the temperature was raised to reflux of the reaction system, and then the temperature was kept and stirred for 4 h. The heating was stopped after the reaction was completed. Intermediate 163-1 (6.3 g, yield 60%) was obtained by column chromatography (n-hexane: dichloromethane volume ratio = 2:1).

[0327] LC-MS (APCI) (M+H) + :587.16.

[0328] 2. Synthesis of Intermediate 163-2

[0329]

[0330] Under nitrogen atmosphere, 163-1 (6.3 g, 10.73 mmol), (2-formylphenyl) boronic acid (4.8 g, 32.20 mmol), sodium tert-butoxide (4.1 g, 42.93 mmol), dichlorodi-tert-butyl-(4-dimethylaminophenyl) phosphine palladium (II) (0.76 g, 1.07 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (1.02 g, 2.15 mmol) were put into a four-necked bottle, and 100 mL of toluene, 40 mL of ethanol and 40 mL of deionized water were added. The temperature was heated to reflux the reaction system, and then the temperature was kept and stirred for 8 hours. The heating was stopped after the reaction was completed. After extraction with dichloromethane, the intermediate 163-2 (5.4 g, yield 77%) was obtained by column chromatography (n-hexane: dichloromethane volume ratio = 3:1).

[0331] LC-MS (APCI) (M+H) + :657.22.

[0332] 3. Synthesis of compound 163

[0333]

[0334] Under nitrogen atmosphere, intermediate 163-2 (5.4 g, 8.23 ​​mmol) was placed in a four-necked flask, 65 mL of trifluoroacetic acid was added, 3 mL of azidotrimethylsilane was slowly added dropwise, and stirred for 5 minutes. After stabilization, 4 mL of trifluoromethanesulfonic acid was slowly added dropwise and stirred for 5 minutes. After stabilization, the temperature was heated to 60 ° C, and then kept warm and stirred for 2 hours. The heating was stopped when the reaction was completed. Column chromatography (n-hexane: dichloromethane volume ratio = 2: 1) gave yellow compound 163 (4.0 g, yield 74%).

[0335] LC-MS (APCI) (M+H) + :654.75.

[0336] 1H NMR(400MHz,Methylene Chloride-d2)δ9.62(d,1H),8.89(d,2H),8.79–8.73(m,4H),8.51(d,1H),8.08– 7.94(m,2H),7.80–7.69(m,5H),7.67–7.62(m,2H),7.55(ddd,9H),7.45(td,1H).

[0337] Synthesis Example 10 Synthesis of Compound No. 183

[0338] 1. Synthesis of intermediate 183-1

[0339]

[0340] 3-Fluorophanthridine (20.0 g, 101.41 mmol), 9-aminophenanthrene (21.55 g, 111.55 mmol), potassium carbonate (28.0 g, 202.82 mmol) and 300 mL of N-N-dimethylformamide were added to a 500 mL four-necked bottle in sequence and refluxed for 6 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure, 500 mL of dichloromethane was added to dissolve and filter, the filtrate was concentrated and dried, and 100 mL of ethyl acetate was used to beat the slurry to obtain intermediate 183-1 (21.75 g, yield 58%).

[0341] LC-MS (APCI) (M+H) + :371.20.

[0342] 2. Synthesis of Intermediate 183-2

[0343]

[0344] In a 1L four-necked bottle, add intermediate 183-1 (21.75 g, 58.70 mmol), 1-methyl-1-phenylhydrazine (17.92 g, 146.75 mmol), 300 mL of ethylene glycol dimethyl ether, and heat to 60°C for 24 hours. After the reaction is complete, concentrate and add 100 mL of toluene for recrystallization to obtain intermediate 183-2 (13.71 g, yield 61%).

[0345] LC-MS (APCI) (M+H) + :386.23.

[0346] 3. Synthesis of compound 183

[0347]

[0348] In a 1L four-necked bottle, add intermediate 183-2 (13.71 g, 35.56 mmol), 9-phenanthaldehyde (8.8 g, 42.67 mmol), sodium bisulfite (1.85 g, 17.78 mmol), 200 mL of N,N-dimethylformamide, and heat to reflux for 2 hours. After the reaction is completed, concentrate, add 500 mL of dichloromethane to dissolve, filter, concentrate the filtrate, and recrystallize with 100 mL of toluene to obtain compound 183 (16.24 g, yield 80%).

[0349] LC-MS (APCI) (M+H) + :571.36.

[0350] 1 H NMR (400MHz, Methylene Chloride-d2) δ8.45 (s, 1H), 8.40–8.34 (m, 2H), 7.70 (d, 3H), 7.48–7.34 (m, 14H), 7.34–7.27 (m, 3H), 7.17 (d, 1H), 7.08 (d, 1H). Synthesis Example 11 Synthesis of Compound No. 204

[0351] 1. Synthesis of Intermediate 204-1

[0352]

[0353] N 2 Under a 1L four-necked bottle, 3-fluorophenanthridine (20 g, 101.41 mmol), 300 mL of N,N-dimethylformamide, 2-amino-9-phenyl-1,10-phenanthroline (33.02 g, 121.70 mmol), and potassium carbonate (42.05 g, 304.24 mmol) were added. The temperature was raised to reflux for reaction for 3 h. The reaction solution was concentrated under reduced pressure, dissolved and filtered with dichloromethane. After the filtrate was concentrated to dryness, it was slurried with ethyl acetate to obtain intermediate 204-1 (27.79 g, yield 61%).

[0354] LC-MS (APCI) (M+H) + :449.53.

[0355] 2. Synthesis of Intermediate 204-2

[0356]

[0357] In a 1L four-necked bottle, add intermediate 204-1 (27.79 g, 61.95 mmol), 1-methyl-1-phenylhydrazine (18.92 g, 154.9 mmol), 300 mL of ethylene glycol dimethyl ether, and heat to 60°C to react for 24 hours. After the reaction is completed, concentrate and add toluene for recrystallization to obtain intermediate 204-2 (17.23 g, yield 60%).

[0358] LC-MS (APCI) (M+H) + :464.54.

[0359] 3. Synthesis of Compound 204

[0360]

[0361] In a 1L four-necked bottle, add intermediate 204-2 (17.23 g, 37.17 mmol), benzaldehyde (5.92 g, 55.76 mmol), sodium bisulfite (1.93 g, 18.59 mmol), 300 mL of N,N-dimethylformamide, and heat to reflux for 2 hours. After the reaction is completed, concentrate, add 500 mL of dichloromethane to dissolve and filter, concentrate the filtrate, and then add chlorobenzene to recrystallize to obtain compound 204 (16.34 g, yield 80%).

[0362] LC-MS (APCI) (M+H) + :550.64.

[0363] 1 H NMR(400MHz,Methylene Chloride-d2)δ8.56(dd,1H),8.35–8.28(m,3H),8.14(dd,2H),7.98(dd,1H),7.83(d,1H),7.74(dd,2H) ,7.71–7.66(m,2H),7.65–7.61(m,2H),7.55(dd,1H),7.52–7.46(m,2H),7.43–7.29(m,5H),7.17(d,1H).

[0364] The following application examples further illustrate the application of the heterocyclic compound of the present invention in the preparation of organic electroluminescent elements.

[0365] Application Example 1

[0366] Device Comparison Example 1

[0367] This embodiment provides an organic electroluminescent element, such as Figure 1As shown, it includes a stacked first electrode layer 1, a hole injection layer 2, a hole transport layer 3, a light-emitting layer 4, an electron transport layer 5, an N-type charge generation layer 6, a P-type charge generation layer 7, a hole transport layer 8, a light-emitting layer 9, an electron transport layer 10, an electron injection layer 11 and a second electrode layer 12, wherein 100 is a first light-emitting unit and 200 is a second light-emitting unit.

[0368] The specific component structure is:

[0369] ITO(100nm) / NPD:F4-TCNQ(10%)(10nm) / NPD(120nm) / BH:BD(3%)(20nm) / TmPyPB(10nm ) / Bphen:Li(2%)(10nm) / NPD:F4-TCNQ(10%)(20nm) / NPD(20nm) / BH:BD(3%)(20nm) / Alq 3 (10nm) / LiF(0.5nm) / Al(200nm).

[0370] Component preparation process:

[0371] The bottom-emitting glass substrate used in this embodiment was purchased from Guangdong Xinli Display Technology Co., Ltd., and 100 nm ITO was used as the first electrode layer 1. First, the bottom-emitting glass substrate was cleaned with ITO cleaning agent, deionized water, and isopropyl alcohol in sequence, and then the bottom-emitting glass substrate was baked at 180 degrees Celsius for 30 minutes to dry it.

[0372] Then put the bottom luminescent glass substrate into the evaporation chamber and place it in a vacuum chamber of about 10 -8Each organic layer was deposited on the ITO anode in sequence by thermal vacuum evaporation at a rate of 0.2-2 angstroms / second under the condition of 1000 Å / s. Among them, F4-TCNQ (mass content 10%) was doped into NPD to form a thickness of 10nm as a hole injection layer. NPD was formed to a thickness of 120nm as a hole transport layer, and the anthracene host ADN (9,10-di(naphtha-2-yl-)anthracene) was doped with a 3% mass content of pyrene dopant 1,6-bis(diphenylamino)pyrene to form a blue light-emitting layer with a thickness of 20nm. TmPyPB was formed to a thickness of 10nm as the first electron transport layer, and BPhen (4,7-Diphenyl-1,10-phenanthroline) was doped with a mass content of 3%. The N-type charge generation layer 6 with a thickness of 10 nm is formed by doping NPD with a mass content of 2% Li, and a P-type charge generation layer with a thickness of 20 nm is formed by doping NPD with a mass content of 10% F4-TCNQ, and NPD is formed into a hole transport layer with a thickness of 20 nm. The anthracene main body ADN (9,10-di(naphtha-2-yl-)anthracene) is doped with a mass content of 3% pyrene dopant 1,6-bis(diphenylamino)pyrene to form a blue light-emitting layer with a thickness of 20 nm. Alq 3 (Tris-(8-hydroxyquinolinato)aluminum) was formed to a thickness of 10 nm as a second electron transport layer, LiF was formed to a thickness of 0.5 nm as an electron injection layer, and Al was formed to a thickness of 200 nm as a cathode.

[0373] Finally, the component was transferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the component, which was recorded as organic electronic component 1.

[0374]

[0375] Contrast structure

[0376] Bphen(4,7-Diphenyl-1,10-phenanthroline)

[0377]

[0378] Device Example 1

[0379] Charge Generation Layer The N-type charge generation layer 6 is prepared by using the compound prepared in Example 1 of the present invention instead of the Bphen material, and the organic electronic element 2 is prepared by the same method.

[0380] Device Example 2

[0381] The charge generation layer uses the compound prepared in Example 2 of the present invention instead of the Bphen material to prepare the N-type charge generation layer 6, and the organic electronic element 3 is manufactured by the same method.

[0382] Device Example 3

[0383] Charge Generation Layer The N-type charge generation layer 6 is prepared by using the compound prepared in Example 3 of the present invention instead of the Bphen material, and the organic electronic element 4 is prepared by the same method.

[0384] Device Example 4

[0385] The charge generation layer uses the compound prepared in Example 4 of the present invention instead of Bphen material to prepare an N-type charge generation layer 6, and the organic electronic element 5 is manufactured using the same method.

[0386] Device Example 5

[0387] Charge Generation Layer The N-type charge generation layer 6 is prepared by using the compound prepared in Example 5 of the present invention instead of the Bphen material, and the organic electronic element 6 is prepared by the same method.

[0388] Device Example 6

[0389] Charge Generation Layer The N-type charge generation layer 6 is prepared by using the compound prepared in Example 6 of the present invention instead of the Bphen material, and the organic electronic element 7 is prepared by the same method.

[0390] Test Results

[0391] Life test method: Apply voltage to the obtained organic electroluminescent element so that the current density reaches 30mA / cm 2 The time until the brightness reaches 95% of the initial brightness (LT95 (unit: hour)) was measured.

[0392] Current efficiency at current density 15mA / cm 2 The following test is performed and the test results are shown in Table 1.

[0393] Table 1

[0394] Current efficiency, cd / A Life LT95, hours Organic electronic component 1 (comparative example) 17.53 58 Organic electronic component 2 (device example 1) 17.62 101 Organic electronic component 3 (device example 1) 17.77 107 Organic electronic component 4 (device example 1) 17.97 115 Organic electronic component 5 (device example 1) 17.62 90 Organic electronic component 6 (device example 5) 17.64 90 Organic electronic component 7 (device embodiment 6) 18.00 93

[0395] According to the results in Table 1, the organic electroluminescent elements 2-7 prepared from the compounds of the present invention have higher current efficiency and longer service life than the organic electroluminescent element 1; therefore, they are suitable for preparing organic electroluminescent elements as N-type charge generation layers.

[0396] Application Example 2

[0397] Device Comparison Example 2

[0398] This embodiment provides an organic electroluminescent device, such as Figure 2 As shown, it includes a first electrode layer 110 , a hole injection layer 120 , a hole transport layer 130 , a light emitting layer 140 , an electron transport layer 150 , an electron injection layer 160 and a second electrode layer 170 .

[0399] The specific device structure is:

[0400] ITO(100nm) / NPD:F4-TCNQ(10%)(10nm) / NPD(120nm) / BH:BD(3%)(20nm) / Alq3:Liq(50%)(10nm) / LiF(0.5nm) / Al(200nm).

[0401] Device preparation process:

[0402] The bottom-emitting glass substrate used in this embodiment was purchased from Guangdong Xinli Display Technology Co., Ltd., and 100 nm ITO was used as the first electrode layer 110. First, the bottom-emitting glass substrate was cleaned with ITO cleaning agent, deionized water, and isopropyl alcohol in sequence, and then the bottom-emitting glass substrate was baked at 180 degrees Celsius for 30 minutes to dry it.

[0403] Then put the bottom luminescent glass substrate into the evaporation chamber and place it in a vacuum chamber of about 10 -8 In the case of 1000 Å / s, each organic layer was deposited on the ITO anode by thermal vacuum evaporation at a rate of 0.2-2 Å / s. Among them, F4-TCNQ (2,3,5,6-Tetrafluoro-tetracyanoquinodimethane) with a mass content of 10% was doped on NPD to form a thickness of 10nm as a hole injection layer, NPD was formed to a thickness of 120nm as a hole transport layer, and 1,6-bis (diphenylamino) pyrene, a 3% pyrene dopant, was doped on the anthracene main body ADN (9,10-di (naphtha-2-yl-) anthracene) to form a blue light-emitting layer with a thickness of 20nm, and Alq 3 (Tris-(8-hydroxyquinolinato)aluminum) is doped with 50% Liq by mass to form an electron transport layer with a thickness of 10nm, LiF (Lithium Fluoride) is formed with a thickness of 0.5nm as an electron injection layer, and Al is formed with a thickness of 200nm as a cathode.

[0404] Finally, the device was transferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the device, which was recorded as organic electronic element 8.

[0405] Device Example 7

[0406] The compound (compound number 4) prepared in Example 1 of the present invention was used to replace the Alq in Comparative Example 2. 3 The electron transport layer is prepared and the organic electronic component 9 is manufactured by the same method.

[0407] Test Results

[0408] Life test method: Apply voltage to the obtained organic electroluminescent element so that the current density reaches 30mA / cm 2 The time until the brightness reaches 95% of the initial brightness (LT95 (unit: hour)) was measured.

[0409] The driving voltage and current efficiency are both at a current density of 15mA / cm 2 The test results are shown in Table 2.

[0410] Table 2

[0411] Drive voltage, V Current efficiency, cd / A Life LT95, hours Organic electronic components8 5.44 5.38 14 Organic electronic components9 3.76 7.50 70

[0412] Compared with the organic electronic element 8, the organic electronic element 9 prepared by using the compound of the present invention has a lower driving voltage, a higher current efficiency and a longer service life. Therefore, the compound of the present invention can also be used as an electron transport layer material for preparing an organic electroluminescent element.

[0413] In this specification, each embodiment is described in a progressive manner, and each embodiment focuses on the differences from other embodiments. The same or similar parts between the embodiments can be referred to each other. For the device disclosed in the embodiment, since it corresponds to the method disclosed in the embodiment, the description is relatively simple, and the relevant parts can be referred to the method part.

[0414] The above is a detailed introduction to a heterocyclic compound provided by the present invention and an organic electroluminescent element containing the heterocyclic compound. Specific examples are used herein to illustrate the principles and implementation methods of the present invention. The description of the above embodiments is only used to help understand the method of the present invention and its core idea. It should be pointed out that for ordinary technicians in this technical field, without departing from the principle of the present invention, the present invention can also be improved and modified in a number of ways, and these improvements and modifications also fall within the scope of protection of the claims of the present invention.

Claims

1. A heterocyclic compound, characterized in that The compound has the structure shown in formula (1): in represents a double bond or a single bond, X 1 Selected from O, S, N, NR, X 2 Selected from O, S, N, NR, L 1 -L 6 are independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group, R, R 1 -R 6 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C3-C60 heterocyclyl, The substituents in the substitution or unsubstitution are each independently selected from one or a combination of deuterium, halogen, cyano, C1-C10 alkyl, C6-C30 aryl, C3-C30 heteroaryl.

2. The heterocyclic compound according to claim 1, characterized in that: The heterocyclic compound is selected from the compounds represented by the following formula (1-1) or formula (1-2), 3. The heterocyclic compound according to claim 1, characterized in that: L 1 -L 6 The following groups are independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted phenylene naphthyl group, a substituted or unsubstituted binaphthylene group, a substituted or unsubstituted fluoranthenylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted benzopyrenylene group, a substituted or unsubstituted ... substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted pyridinylene; R, R 1 -R 6 each independently selected from the following groups: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloadamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted indenyl, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted substituted or unsubstituted pyridyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazine, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted benzoxazolyl, substituted substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted thienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl.

4. The heterocyclic compound according to claim 3, characterized in that: The substituents in the substituted or unsubstituted groups are each independently selected from one or more combinations of deuterium, halogen, cyano, C1-C10 alkyl, C6-C30 aryl, C3-C30 heteroaryl, and the substituted group may be substituted at one or more positions.

5. The heterocyclic compound according to claim 3, characterized in that: In formula (1), One of them is a single bond and the other is a double bond; The heteroatom of the heteroaryl, heteroarylene and heterocyclic group is selected from O, S, N, P or Si.

6. Use of the heterocyclic compound according to any one of claims 1 to 5 as an organic electroluminescent element material.

7. An organic electroluminescent element comprising an anode, a cathode, and an organic layer located between the anode and the cathode, characterized in that: The organic layer comprises the heterocyclic compound according to any one of claims 1 to 5.

8. The organic electroluminescent element according to claim 8, characterized in that: The organic layer comprises an electron transport layer and a light emitting layer, and the electron transport layer comprises the heterocyclic compound according to any one of claims 1 to 5.

9. The organic electroluminescent element according to claim 9, characterized in that: The organic layer comprises at least two light-emitting units, a charge generation layer is comprised between the light-emitting units, the light-emitting units comprise an electron transport layer, and the at least one charge generation layer and / or at least one electron transport layer comprises the heterocyclic compound according to any one of claims 1 to 5.

10. An electronic device comprising one or more of a display, a monitor, and a lighting device, and comprising the organic electroluminescent element according to claim 7.

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