Organic electroluminescent material and organic electroluminescent element containing same

Abstract

The invention relates to a light-emitting material and an organic electroluminescent element comprising the same. The organic electroluminescent material not only can be used as a high-performance charge generation layer material, but also can be used for one or more layers of single-layer or laminated devices such as an electron transport layer and a hole blocking layer. Organic electroluminescent material having a structure represented by formula (1) # imgabs0 #

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescence, and in particular relates to an organic electroluminescent material and an organic electroluminescent element containing the same. Background Art

[0002] Organic semiconductor materials are versatile in synthesis, have relatively low manufacturing costs, and have excellent optical and electrical properties. Organic light-emitting diodes (OLEDs) have great potential for application in optoelectronic devices such as flat panel displays and lighting.

[0003] From the perspective of device structure, OLED device structures are classified into many types according to the structure of the light-emitting layer, such as single light-emitting layer, multi-doped light-emitting layer, multiple light-emitting layer, stacked structure, etc. In stacked devices, due to the different transmission rates of electrons and holes in OLED devices, the number of carriers in the light-emitting area is unbalanced, which limits the improvement of the exciton recombination rate, resulting in low device efficiency and high driving voltage. Adding a charge generation layer between the light-emitting units can effectively improve the problem of unbalanced number of carriers in the device. However, there is a lack of high-performance materials that can be used for the charge generation layer of stacked devices, and the current efficiency and service life are still not ideal, which limits the choice of device design. Therefore, continuing the research and development of light-emitting layer materials is of great significance for designing OLED device structures and improving performance. Summary of the invention

[0004] The purpose of the present invention is to provide an organic electroluminescent material, which can not only be used as a high-performance charge generation layer material, but also can be used for one or more layers of single-layer or stacked devices such as electron transport layers and hole blocking layers. The application of the organic electroluminescent material in organic electroluminescent elements can improve the defects of low current efficiency and short service life in the prior art.

[0005] The technical solution adopted by the present invention to solve its technical problem is:

[0006] An organic electroluminescent material having a structure shown in formula (1):

[0007] in

[0008] represents a double bond or a single bond,

[0009] X 1 Selected from O, S, N, NR, X 2 is selected from O, S, N, and NR, R is selected from hydrogen, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl,

[0010] L 1 -L 4are each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group,

[0011] R 1 -R 4 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 C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl,

[0012] In the “substituted or unsubstituted”, the substituents when substituted are each independently selected from deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C3-C30 heteroaryl, C6-C30 aryl, and C7-C30 aralkyl.

[0013] Preferably, when R 1 Phenyl, L 1 is a single bond, X 1 N, X 2 For O, L 2 -L 4 At the same time, R 2 -R 4 When any two of them are hydrogen, the other is not phenyl or dibenzofuran; more preferably, when R 1 Phenyl, L 1 is a single bond, X 1 N, X 2 For O, L 2 -L 4 At the same time, R 2 , R 3 When both are hydrogen, R 4 Not phenyl or dibenzofuran.

[0014] Preferably, when R 1 Phenyl, L 1 is a single bond, X 2 N, X 1 O or S and -L 2 -R 2 , -L 3 -R 3 , -L 4 -R 4 When any two of them are -H, the other is not a methyl group substituted by anthracene substituted by a methyl group; more preferably, when R 1 Phenyl, L 1 is a single bond, X 2 N, X 1 O or S and -L2 -R 2 , -L 3 -R 3 When both are -H, -L 4 -R 4 It is not a methyl group substituted with anthracene group substituted with a methyl group.

[0015] Preferably, when R 1 Phenyl, L 1 is a single bond, X 2 N, X 1 S and -L 2 -R 2 , -L 3 -R 3 , -L 4 -R 4 When any two of them are -H, the other is not a methyl group substituted by dimethylfluorene; preferably, when R 1 Phenyl, L 1 is a single bond, X 2 N, X 1 S and -L 2 -R 2 , -L 3 -R 3 , -L 4 -R 4 When any two of them are -H, the other is not a methyl group substituted by 9,9-dimethylfluorene; more preferably, when R 1 Phenyl, L 1 is a single bond, X 2 N, X 1 S and -L 2 -R 2 , -L 3 -R 3 When both are -H, -L 4 -R 4 It is not a methyl group substituted by 9,9-dimethylfluorene.

[0016] Preferably, the organic electroluminescent material is selected from the compounds represented by the following formula (1-1) and formula (1-2):

[0017]

[0018] X 1 , X 2 , L 1 -L 4 , R 1 -R 4 The definition of is the same as that of formula (1).

[0019] Preferably, the C6-C60 arylene group is selected from phenylene, biphenylene, terphenylene, phenylene naphthyl, naphthyl naphthyl, phenylene phenanthryl, phenylene phenanthryl, phenylene anthracenyl, naphthyl anthracenyl, naphthyl, anthracenyl, phenanthryl, fluoranthenyl, triphenylene, perylene, pyrenyl, benzopyrenyl, ... Benzoyl base;

[0020] Preferably, the C3-C60 heteroarylene group is selected from dibenzofuranyl, dibenzothienyl, pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, triazinyl, indolizinyl, indolyl, indolopyridyl, purinyl, phenanthroline, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, thiazolyl, imidazolyl, oxazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzothiazolyl, benzimidazolyl, benzooxazolyl, carbazolyl;

[0021] Preferably, the C1-C10 alkyl group is selected from methyl, ethyl, propyl, isopropyl, tert-butyl, and pentyl;

[0022] Preferably, the C3-C10 cycloalkyl group is selected from cyclopropyl, cyclohexyl, and adamantyl;

[0023] Preferably, the C6-C60 aryl group is selected from phenyl, biphenyl, terphenyl, phenylnaphthyl, naphthylnaphthyl, phenylphenanthryl, naphthylphenanthryl, phenylanthryl, naphthylanthryl, naphthyl, anthracenyl, phenanthryl, fluoranthenyl, triphenylene, peryl, pyrenyl, benzopyrenyl, Benzo base;

[0024] Preferably, the C3-C60 heteroaryl group is selected from dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazine, indolizinyl, indolyl, indolopyridinyl, purinyl, phenanthroline, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, thiazolyl, imidazolyl, oxazolyl, furanyl, thienyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzimidazolyl, benzoxazolyl, and carbazolyl.

[0025] Preferably, L 2 , L 3 Select from single bonds.

[0026] Preferably, R 2 , R 3 Selected from hydrogen.

[0027] Preferably, L 1 It is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group.

[0028] Preferably, L 4 It is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group.

[0029] Preferably, R 1 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 C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.

[0030] Preferably, R 4 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 C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.

[0031] Preferably, L 1 is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted phenylene naphthyl, a substituted or unsubstituted naphthylene naphthyl, a substituted or unsubstituted phenylene phenanthryl, a substituted or unsubstituted naphthylene phenanthryl, a substituted or unsubstituted phenylene anthracenyl, a substituted or unsubstituted naphthylene anthracenyl, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthracenyl, 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 benzo substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenylene;

[0032] Preferably, L 4 is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted phenylene naphthyl, a substituted or unsubstituted naphthylene naphthyl, a substituted or unsubstituted phenylene phenanthryl, a substituted or unsubstituted naphthylene phenanthryl, a substituted or unsubstituted phenylene anthracenyl, a substituted or unsubstituted naphthylene anthracenyl, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthracenyl, 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 benzo substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenylene;

[0033] Preferably, R 1 is selected from hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, cyclohexyl, adamantyl, halogen, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted naphthylnaphthyl, substituted or unsubstituted phenylphenanthrenyl, substituted or unsubstituted naphthylphenanthrenyl, substituted or unsubstituted phenylanthracenyl, substituted or unsubstituted naphthylanthracenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted perylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted Benzoyl, substituted or unsubstituted substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl;

[0034] Preferably, R 4 is selected from hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, cyclohexyl, adamantyl, halogen, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted naphthylnaphthyl, substituted or unsubstituted phenylphenanthrenyl, substituted or unsubstituted naphthylphenanthrenyl, substituted or unsubstituted phenylanthracenyl, substituted or unsubstituted naphthylanthracenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted perylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted Benzoyl, substituted or unsubstituted substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl.

[0035] In the above “substituted or unsubstituted”, the substituents when substituted are each independently selected from deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C3-C30 heteroaryl, and C6-C30 aryl.

[0036] Preferably, the substituent in the above "substituted or unsubstituted" is at least one substituent selected from the group consisting of the following groups: deuterium; cyano; halogen; C1-C10 alkyl, preferably C1-C5 alkyl, more preferably C1-C3 alkyl; C3-C10 cycloalkyl, preferably C3-C6 cycloalkyl; C6-C30 aryl, preferably C6-C20 aryl, more preferably C6-C10 aryl; C7-C30 aralkyl, preferably C7-C20 aralkyl.

[0037] Preferably, the substituents in the above “substituted or unsubstituted” are each independently selected from deuterium, halogen, cyano, methyl, ethyl, tert-butyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyrene, fluoranthenyl, triphenylene, A combination of one or more of phenyl, pyridyl, pyrimidinyl, triazine, phenazine, quinolyl, isoquinolyl and tolyl.

[0038] Preferably, in the formula (1-1), when R 1 Phenyl, L 1 is a single bond, X 2 For O, L 2 -L 4 At the same time, R 2 -R 4 When any two of them are hydrogen, the other is not phenyl or dibenzofuran; more preferably, when R 1 Phenyl, L 1 is a single bond, X 2 For O, L 2 -L 4 At the same time, R 2 , R 3 When both are hydrogen, R 4 Not phenyl or dibenzofuran.

[0039] Preferably, in the formula (1-2), when R 1 Phenyl, L 1 is a single bond, X 1 O or S and -L 2 -R 2 , -L 3 -R 3 , -L 4 -R 4 When any two of them are -H, the other is not a methyl group substituted by anthracene substituted by a methyl group; more preferably, when R 1 Phenyl, L 1 is a single bond, X 1 O or S and -L 2 -R 2 , -L 3 -R3 When both are -H, -L 4 -R 4 It is not a methyl group substituted with anthracene group substituted with a methyl group.

[0040] Preferably, in the formula (1-2), when R 1 Phenyl, L 1 is a single bond, X 1 S and -L 2 -R 2 , -L 3 -R 3 , -L 4 -R 4 When any two of them are -H, the other is not a methyl group substituted by dimethylfluorene; preferably, when R 1 Phenyl, L 1 is a single bond, X 1 S and -L 2 -R 2 , -L 3 -R 3 , -L 4 -R 4 When any two of them are -H, the other is not a methyl group substituted by 9,9-dimethylfluorene; more preferably, when R 1 Phenyl, L 1 is a single bond, X 1 S and -L 2 -R 2 , -L 3 -R 3 When both are -H, -L 4 -R 4 It is not a methyl group substituted by 9,9-dimethylfluorene.

[0041] Preferably, the organic electroluminescent material is selected from the compounds represented by the following formulae (1-3) to (1-6):

[0042]

[0043] Preferably, in formula (1-3) and (1-5), X 2 Selected from O.

[0044] Preferably, in formula (1-3) and (1-5), X 2 Selected from S.

[0045] Preferably, in formula (1-4) and (1-6), X 1 Selected from O.

[0046] Preferably, in formula (1-4) and (1-6), X 1 Selected from S.

[0047] Preferably, in formula (1-5) and (1-6), X 1 Select from O or S, X 2 Select from O or S.

[0048] In formula (1-3) and (1-4), X 1 Select from O or S, X 2 Select from O or S.

[0049] Preferably, in formula (1-3) and / or formula (1-4),

[0050] L 1 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group,

[0051] R 1 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 C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.

[0052] Preferably, L 1 is selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted phenylene naphthyl, substituted or unsubstituted naphthylene naphthyl, substituted or unsubstituted phenylene phenanthryl, substituted or unsubstituted naphthylene phenanthryl, substituted or unsubstituted phenylene anthracenyl, substituted or unsubstituted naphthylene anthracenyl, substituted or unsubstituted naphthylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted perylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted pyrenyl substituted or unsubstituted benzo substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenylene, R 1 is selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, cyclohexyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted Benzoyl, substituted or unsubstituted substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl.

[0053] Preferably, in formula (1-5) and / or formula (1-6),

[0054] L 1 , L 4 are each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, R 1 , R 4 Each is 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 C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.

[0055] Preferably, L 1 is selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted phenylene naphthyl, substituted or unsubstituted naphthylene naphthyl, substituted or unsubstituted phenylene phenanthryl, substituted or unsubstituted naphthylene phenanthryl, substituted or unsubstituted phenylene anthracenyl, substituted or unsubstituted naphthylene anthracenyl, substituted or unsubstituted naphthylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted perylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted pyrenyl substituted or unsubstituted benzo substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenylene, R 1 is selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, cyclohexyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted Benzoyl, substituted or unsubstituted substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl,

[0056] Preferably, L 4is selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted phenylene naphthyl, substituted or unsubstituted naphthylene naphthyl, substituted or unsubstituted phenylene phenanthryl, substituted or unsubstituted naphthylene phenanthryl, substituted or unsubstituted phenylene anthracenyl, substituted or unsubstituted naphthylene anthracenyl, substituted or unsubstituted naphthylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted perylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted pyrenyl substituted or unsubstituted benzo substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenylene, R 4 is selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, cyclohexyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted Benzoyl, substituted or unsubstituted substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl.

[0057] More preferably, in formula (1-5) and / or (1-6), L 1 Selected from single bonds, R 1 is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, L 4 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, R 4 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 C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.

[0058] More preferably, in formula (1-5) and / or (1-6),

[0059] L 1 Selected from single bonds, R 1 is selected from hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, cyclohexyl, adamantyl,

[0060] L4 is selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted phenylene naphthyl, substituted or unsubstituted naphthylene naphthyl, substituted or unsubstituted phenylene phenanthryl, substituted or unsubstituted naphthylene phenanthryl, substituted or unsubstituted phenylene anthracenyl, substituted or unsubstituted naphthylene anthracenyl, substituted or unsubstituted naphthylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted perylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted pyrenyl substituted or unsubstituted benzo substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenylene, R 4 is selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, cyclohexyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted Benzoyl, substituted or unsubstituted substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl.

[0061] Preferably, in the formula (1-5), when R 1 Phenyl, L 1 is a single bond, X 2 For O, L 4 When it is a single bond, R 4 Not phenyl or dibenzofuran.

[0062] Preferably, in the formula (1-6), when R 1 Phenyl, L 1 is a single bond, X 1 When it is O or S, -L 4 -R 4 It is not a methyl group substituted with anthracene group substituted with a methyl group.

[0063] Preferably, in the formula (1-6), when R 1 Phenyl, L 1 is a single bond, X 1 When it is S, -L 4 -R 4 is not a methyl group substituted by dimethylfluorene; preferably, when R 1 Phenyl, L 1 is a single bond, X 1When it is S, -L 4 -R 4 It is not a methyl group substituted by 9,9-dimethylfluorene.

[0064] Preferably, in formula (1-5) and / or formula (1-6),

[0065] R 1 , R 4 At least one of Where R 10 -R 19 is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl,

[0066] R 10 -R 19 Each exists independently or R 10 -R 19 Two adjacent ones of the rings may be connected to each other to form a ring C, and the ring C is selected from a substituted or unsubstituted C3-C30 ring.

[0067] Preferably, in formula (1-5) and / or formula (1-6), R 1 , R 4 One of the selected Where R 10 -R 19 is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C3-C10 heteroaryl, R 1 , R 4 The other one is 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 C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl,

[0068] R 10 -R 19 Each exists independently or R 10 -R 19Two adjacent rings in the ring may be connected to each other to form a ring C, and the ring C is selected from a substituted or unsubstituted C3-C30 ring. Preferably, the ring C is selected from a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C2-C10 heterocycloalkyl, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C3-C30 heteroaryl; more preferably selected from a substituted or unsubstituted C6-C30 aryl; more preferably selected from a substituted or unsubstituted C6-C10 aryl; more preferably selected from a substituted or unsubstituted naphthyl or phenyl; particularly preferably selected from a substituted or unsubstituted phenyl; most preferably selected from a phenyl.

[0069] Preferably, L 1 , L 4 Each is independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group.

[0070] Preferably, L 1 , L 4 each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted phenylene naphthyl, a substituted or unsubstituted naphthylene naphthyl, a substituted or unsubstituted phenylene phenanthryl, a substituted or unsubstituted naphthylene phenanthryl, a substituted or unsubstituted phenylene anthracenyl, a substituted or unsubstituted naphthylene anthracenyl, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthracenyl, 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 benzo substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenylene.

[0071] Preferably, R 1 , R 4 Central Africa The radical is selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, cyclohexyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted Benzoyl, substituted or unsubstituted substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl.

[0072] More preferably, R 1, R 4 Central Africa The group is selected from deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, cyclohexyl, and adamantyl.

[0073] More preferably, R 1 , R 4 Central Africa The group is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted Benzoyl, substituted or unsubstituted substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl.

[0074] Preferably, R 10 -R 19 The independently existing groups are each independently selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, cyclohexyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl.

[0075] Preferably, X 2 Selected from O.

[0076] Preferably, X 1 Selected from O.

[0077] Preferably, in formula (1-5) and / or formula (1-6),

[0078] R 1 , R 4 At least one of Where R 21 -R 28 Each is independently selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.

[0079] Preferably, in formula (1-5) and / or formula (1-6), R 1 , R 4 One of them is selected from Where R 21 -R 28 are each independently selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C3-C10 heteroaryl, R 1 , R 4 The other one is 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 C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.

[0080] Preferably, L 1 , L 4 Each is independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group.

[0081] More preferably, L 1 , L 4 All are selected from single bonds.

[0082] More preferably, L 1 , L 4 Each is independently selected from a substituted or unsubstituted C6-C30 arylene group and a substituted or unsubstituted C3-C30 heteroarylene group.

[0083] Preferably, L 1 , L 4 each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted phenylene naphthyl, a substituted or unsubstituted naphthylene naphthyl, a substituted or unsubstituted phenylene phenanthryl, a substituted or unsubstituted naphthylene phenanthryl, a substituted or unsubstituted phenylene anthracenyl, a substituted or unsubstituted naphthylene anthracenyl, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthracenyl, 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 benzo More preferably, L 1 , L 4are each independently selected from a single bond, or, L 1 , L 4 Each is independently selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted phenylene naphthyl, substituted or unsubstituted naphthylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenylene; most preferably, L 1 , L 4 Each is independently selected from phenylene, biphenylene, phenylene naphthyl, naphthylene, dibenzofuranylene, and dibenzothiophenylene.

[0084] Preferably, R 1 , R 4 Central Africa The radical is selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, cyclohexyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted Benzoyl, substituted or unsubstituted substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl.

[0085] More preferably, R 1 , R 4 Central Africa The group is selected from deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, cyclohexyl, and adamantyl.

[0086] More preferably, R 1 , R 4 Central Africa The group is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted Benzoyl, substituted or unsubstituted substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl.

[0087] Preferably, R 21 -R 28are each independently selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, cyclohexyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl; preferably, R 21 -R 28 are all selected from hydrogen, or, R 21 -R 28 Each is independently selected from deuterium, halogen, cyano, methyl, tert-butyl, cyclohexyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl; more preferably, R 21 -R 28 are all selected from hydrogen, or, R 21 -R 28 are selected from substituted or unsubstituted phenyl; most preferably, R 21 -R 28 are all selected from hydrogen, or, R 21 -R 28 are selected from phenyl.

[0088] Preferably, X 2 Selected from O.

[0089] Preferably, X 1 Selected from O.

[0090] Preferably, the organic electroluminescent material has a chemical structure shown in formula (1-7),

[0091] L 1 -L 5 are each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group,

[0092] R 1 -R 5 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 C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl,

[0093] In the “substituted or unsubstituted”, the substituents when substituted are each independently selected from deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C3-C30 heteroaryl, C6-C30 aryl, and C7-C30 aralkyl.

[0094] Preferably, the organic electroluminescent material has a chemical structure shown in formula (1-8), Formula (1-8).

[0095] Preferably, L 1 , L 5 Each is independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group.

[0096] Preferably, R 1 , R 5 Each is 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 C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.

[0097] Preferably, L 1 , L 5 each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted phenylene naphthyl, a substituted or unsubstituted naphthylene naphthyl, a substituted or unsubstituted phenylene phenanthryl, a substituted or unsubstituted naphthylene phenanthryl, a substituted or unsubstituted phenylene anthracenyl, a substituted or unsubstituted naphthylene anthracenyl, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthracenyl, 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 benzo substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenylene.

[0098] Preferably, R 1 , R 5The independently existing groups are each independently selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, cyclohexyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted Benzoyl, substituted or unsubstituted substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted indenyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuran ... any one of a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted carbolyl group, a substituted or unsubstituted 9,9-dimethylfluorene, a substituted or unsubstituted 9,9-diphenylfluorene, a substituted or unsubstituted spirobifluorene, a substituted or unsubstituted phenanthroline group, a substituted or unsubstituted benzoquinolyl group, a substituted or unsubstituted benzisoquinolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted benzopyrazolyl group, and a substituted or unsubstituted naphthyridinyl group.

[0099] Preferably, the organic electroluminescent material is selected from any one of the following compounds No. 1 to 281:

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119] An application of the organic electroluminescent material of the present invention as an organic electroluminescent element material.

[0120] An application of the organic electroluminescent material of the present invention as an N-type charge generation layer material.

[0121] An organic electroluminescent element comprises a first electrode, a second electrode and an organic layer between the first electrode and the second electrode. The organic layer has one or more layers, at least one of which contains the organic electroluminescent material of the present invention.

[0122] Preferably, the organic layer further comprises at least two light-emitting units, and a charge generation layer is comprised between the at least two light-emitting units, wherein the charge generation layer comprises the organic electroluminescent material described in the present invention.

[0123] Preferably, the charge generation layer comprises an N-type charge generation layer and a P-type charge generation layer, and the N-type charge generation layer comprises the organic electroluminescent material described in the present invention.

[0124] Preferably, the N-type charge generation layer further comprises an alkali metal or an alkaline earth metal.

[0125] An electronic device includes one or more of a display, a monitor, and a lighting device, including the organic electroluminescent element of the present invention; and a control unit for driving the display device.

[0126] In general, compared with the prior art, the above technical solutions conceived by the present invention can achieve the following

[0127] Beneficial effects:

[0128] 1. The compound of the present invention has a nitrogen-containing heterocycle, which can improve the exciton recombination efficiency and thus improve the device efficiency.

[0129] 2. The organic electroluminescent element prepared by using the compound of the present invention has a more durable service life. BRIEF DESCRIPTION OF THE DRAWINGS

[0130] Figure 1 It is a schematic diagram of the structure of the organic electroluminescent element described in the application example, wherein, a 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. DETAILED DESCRIPTION

[0131] In order to more fully describe the present invention to those skilled in the art, embodiments of the present invention are provided. The scope of the present invention is not limited to the following embodiments. These embodiments can make the present invention more thorough and complete, and fully convey the viewpoints of the present invention to those skilled in the art.

[0132] Unless otherwise specified, the experimental methods used in the following examples are all conventional methods; the reagents, materials, etc. used in the following examples, unless otherwise specified, can be obtained from commercial channels.

[0133] As used herein, the term "halogen" may include fluorine, chlorine, bromine or iodine.

[0134] 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.

[0135] 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.

[0136] 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.

[0137] 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.

[0138] As used in the present invention, the term "C6-C60 aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having a monocyclic ring or a combination of two or more rings and having 6 to 60 carbon atoms. Further, such an aryl may have a form in which two or more rings are simply lateral or fused to each other. Examples of such aryl groups include, but are not limited to, phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, pyrenyl, triphenylene, fluoranthenyl, dimethyl 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirobifluorenyl, etc.

[0139] As used in the present invention, the term "C6-C30 aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having a monocyclic ring or a combination of two or more rings and having 6 to 30 carbon atoms. Further, such an aryl may have a form in which two or more rings are simply lateral to each other or fused to each other. Examples of such aryl groups include, but are not limited to, phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, pyrenyl, triphenylene, fluoranthenyl, dimethyl 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirobifluorenyl, etc.

[0140] As used in the present invention, the term "C6-C10 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 10 carbon atoms. Further, such an aryl group may have a form in which two or more rings are simply lateral to each other or fused to each other. Examples of such an aryl group include, but are not limited to, phenyl, naphthyl, and the like.

[0141] 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.

[0142] 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.

[0143] As used in the present invention, the term "C3-C30 heteroaryl group" refers to a monovalent substituent derived from a monocyclic heterocyclic or polycyclic aromatic hydrocarbon having 3 to 30 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.

[0144] As used in the present invention, the term "C3-C10 heteroaryl" refers to a monovalent substituent derived from a monocyclic or polycyclic aromatic hydrocarbon having 3 to 10 carbon atoms. In this connection, at least one carbon in the ring, preferably 1-3 carbons, is substituted by a heteroatom, such as N, O, S, P, B or Si. In addition, this heteroaryl can have a form in which two or more rings are simply lateral to each other or fused to each other or fused to an aryl. Examples of this heteroaryl include pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, thiazolyl, imidazolyl, oxazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzothiazolyl, benzimidazolyl, benzoxazolyl, etc., and the present invention is not limited thereto.

[0145] 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.

[0146] As used in the present invention, the term "C7-C30 aralkyl" refers to a monovalent substituent derived from an aromatic hydrocarbon substituted with an alkyl group having 3 to 30 carbon atoms. Examples of such aralkyl groups include, but are not limited to, tolyl, xylyl, ethylphenyl, and the like.

[0147] As used in the present invention, the term "C7-C20 aralkyl" refers to a monovalent substituent derived from an alkyl-substituted aromatic hydrocarbon having 3 to 20 carbon atoms. Examples of such aralkyl include, but are not limited to, tolyl, xylyl, ethylphenyl, and the like.

[0148] As used in the present invention, "R 10 -R 19 Two adjacent groups may be connected to each other to form a ring C", wherein the ring C may be composed of two substituents connected or a substituent connected to a hydrogen. 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 , R 19 and R 10 .

[0149] As used in the present invention, the "substituted or unsubstituted C3-C30 ring" refers to a ring group having 3 to 30 carbon atoms in the ring.

[0150] As used in the present invention, the "substituted or unsubstituted C6-C30 aromatic ring" refers to an aromatic ring group having 6 to 30 carbon atoms in the ring, for example, R 16 and R 17 Connected to each other to form benzene rings The number of ring atoms includes two carbon atoms, C1 and C2.

[0151] As used in the present invention, the "carbon number is XY" in the expression "Z group having carbon number XY" or "Z group of C(XY)" 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-C60 aromatic group means that when it is unsubstituted, the carbon number of the aromatic group is any integer between 6 and 60, that is, the carbon number when unsubstituted can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20...60.

[0152] As used in the present invention, the term "single bond" refers to a direct connection of groups, for example, L in formula (1) 1 is a single bond, which means Wherein formula (1) is the following structure

[0153] 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,

[0154]

[0155] Indicates the position of substitution. "Unsubstituted" means that hydrogen atoms remain, in this case, hydrogen atoms include protium, deuterium, tritium.

[0156] When two or more substituents are present, the two or more substituents may be the same or different.

[0157] As used herein, the term "phenylene naphthyl" refers to

[0158] As used herein, the term "phenylnaphthyl" includes

[0159] As used in the present invention, "*" refers to a linking site.

[0160] 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.

[0161] 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.

[0162] Organic electroluminescent element

[0163] The structure of the organic electroluminescent element of the present invention is a disclosed structure, comprising a first electrode, a second electrode and an organic layer located between the first electrode and the second electrode, 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.

[0164] 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.

[0165] 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.

[0166] As simple light emitting elements, the following may be cited, but are not limited thereto:

[0167] (1) hole transport layer / fluorescent light emitting layer / electron transport layer;

[0168] (2) hole transport layer / phosphorescent light emitting layer / electron transport layer;

[0169] (3) hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / electron transport layer;

[0170] (4) hole transport layer / first phosphorescent light-emitting layer / second phosphorescent light-emitting layer / electron transport layer;

[0171] (5) hole transport layer / fluorescent emitting layer / spacer layer / phosphorescent emitting layer / electron transport layer;

[0172] (6) hole transport layer / electron blocking layer / fluorescent emitting layer / electron transport layer;

[0173] (7) hole transport layer / electron blocking layer / fluorescent light emitting layer / hole blocking layer / electron transport layer;

[0174] (8) hole transport layer / electron blocking layer / phosphorescent light emitting layer / electron transport layer;

[0175] (9) hole transport layer / electron blocking layer / phosphorescent emitting layer / hole blocking layer / electron transport layer;

[0176] (10) hole injection layer / hole transport layer / phosphorescent light emitting layer / electron transport layer / electron injection layer;

[0177] (11) hole injection layer / hole transport layer / fluorescent light emitting layer / electron transport layer / electron injection layer;

[0178] (12) hole injection layer / hole transport layer / electron blocking layer / phosphorescent light emitting layer / electron transport layer / electron injection layer;

[0179] (13) hole injection layer / hole transport layer / electron blocking layer / fluorescent light emitting layer / electron transport layer / electron injection layer;

[0180] The phosphorescent / fluorescent light-emitting layers mentioned above can each emit light of a different color.

[0181] As a tandem type organic electroluminescent element, it can be a first electrode / first light-emitting unit / intermediate layer / second light-emitting unit / second electrode. 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.

[0182] 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.

[0183] 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.

[0184] As the first electrode material, a material having a relatively large work function can be used, and a transparent conductive oxide, a metal, a conductive polymer, etc. can be used. Specific examples of the first electrode 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.

[0185] As the second electrode 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 the second electrode material 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.

[0186] 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.

[0187] 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 first electrode 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.

[0188] 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.

[0189] 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 second electrode 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.

[0190] 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.

[0191] The hole blocking layer is a layer that blocks holes from reaching the second electrode.

[0192] The electron blocking layer is a layer that blocks electrons from reaching the first electrode.

[0193] The organic light-emitting element of the present specification may be a top-emitting element, a bottom-emitting element, or a dual-emission element depending on the materials used.

[0194] The charge generation layer refers to the middle layer between the first electrode and the second electrode in the 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 second electrode side and an N-type layer on the first electrode side, which can effectively separate charges and effectively transfer carriers.

[0195] 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.

[0196] 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.

[0197] 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.

[0198]

[0199]

[0200] The same synthesis method can be used for different substitution positions. 1 , X 2 , L 1 -L 4 , R 1 -R 4 With X in formula (1) 1 , X 2 , L 1 -L 4 , R1 -R 4 The meaning expressed is the same.

[0201] Example 1: Synthesis of Compound 19

[0202] (1) Synthesis of Intermediate 19-1

[0203]

[0204] 8-Aminoquinolin-7-ol (20 g, 125 mmol), carbon disulfide (12.4 mL, 250 mmol), 1 mol / L aqueous NaOH solution (200 mL) and MeOH (300 mL) were heated at 50°C for 3 days. 2 mol / L aqueous HCl solution (100 mL) was added, and ethyl acetate was added for extraction. The aqueous layer was extracted with ethyl acetate again, and the combined organic layers were treated with MgSO 4 Dry and concentrate to obtain 26.4 g of a white solid. The white solid was added to a mixed solution of 200 mL of thionyl chloride and 20 mL of DMF, and the mixture was stirred at room temperature overnight. The solvent was evaporated, and chloroform and water were added. The aqueous layer was extracted with chloroform, and the organic phase was concentrated and purified by column chromatography (elution with n-hexane: methanol volume ratio = 1:10) to obtain a white intermediate 19-1 (18 g, yield: 70%).

[0205] LC-MS(APCI):205.10[M+H]+.Calcd for:C 10 H 5 C1N 2 O: 204.01

[0206] (2) Synthesis of Intermediate 19-2

[0207]

[0208] In a 500 mL four-necked bottle, intermediate 19-1 (18 g, 87.8 mmol), 4-bromophenylboronic acid pinacol ester (26 g, 92.1 mmol), K 2 CO 3 (24 g, 174 mmol), tetrakis(triphenylphosphine)palladium (0.9 g, 1.7 mmol) and 150 mL of THF and 50 mL of H 2 The mixed solution of 1,2-dihydro-1-nitrogen-2-ol was heated to reflux for 4 h under nitrogen atmosphere, and the product precipitated. The mixture was cooled to room temperature and filtered, and washed with n-hexane to obtain intermediate 19-2 (19 g, yield: 67%).

[0209] LC-MS(APCI):324.99[M+H]+.Calcd for:C 16 H 9 Bn2 O: 323.99

[0210] (3) Synthesis of Compound 19

[0211]

[0212]

[0213] To a 500 mL four-necked flask were added, intermediate 19-2 (19 g, 58.6 mmol), pyrenyl-1-boronic acid pinacol ester (20 g, 60 mmol), K 2 CO 3 (16 g, 117 mmol), tetrakis(triphenylphosphine)palladium (1.3 g, 1.17 mmol) and 150 mL of THF and 50 mL of H 2 The mixed solution of 1,2-dihydro-1,4-dihydro-2-nitrogen-2-ol was heated to reflux for 2 h under a nitrogen environment, and the product precipitated. The mixture was cooled to room temperature and filtered, and washed with n-hexane to obtain compound 19 (22 g, yield 84%).

[0214] LC-MS(APCI):447.14[M+H]+.Calcd for:C 32 H 18 N 2 O:446.14

[0215] 1H NMR(400MHz,Methylene Chloride-d2)δ8.99(dd,1H),8.54–8.47(m,2H),8.27(dd,1H),8.24–8.11(m,4H),8.09–7.94(m,5H),7.87–7.76(m,4H),7.45(dd,1H).

[0216] Example 2: Synthesis of Compound 32

[0217] (1) Synthesis of Intermediate 32-1

[0218]

[0219] Under nitrogen atmosphere, 2-chloroquinoline-7-ol (20 g, 111 mmol) and 1-methyl-1-phenylhydrazine (27 g, 222 mmol) were placed in a four-necked reaction bottle, and 200 mL of chlorobenzene was added, and the temperature was heated to 110±2° C. TLC was used to monitor until the reaction of the raw materials was complete (about 24 h). After the reaction was completed, the reaction solution was cooled to room temperature, quenched by adding 300 mL of water, extracted with ethyl acetate, and dried to obtain a brown intermediate 32-1 (18 g, yield 85%).

[0220] LC-MS(APCI): 195.05(M+H+).Calcd for:C 9 H 7 C1N 2 O: 194.02

[0221] (2) Synthesis of Intermediate 32-2

[0222]

[0223] Under nitrogen atmosphere, intermediate 32-1 (18 g, 92.7 mmol) and benzoyl chloride (19.5 g, 139.2 mmol) were placed in a four-necked reaction bottle, and 200 mL of 1,4-dioxane was added, and then trifluoromethanesulfonic acid (20.8 g, 139.1 mmol) was added dropwise and heated to reflux for reaction. After the reaction was completed, the reaction solution was cooled to room temperature, quenched by adding 300 mL of water, extracted with ethyl acetate, and purified by column chromatography (eluted with n-hexane) to obtain intermediate 32-2 (15 g, yield 58%).

[0224] LC-MS(APCI): 281.07(M+H+).Calcd for:C 16 H 9 C1N 2 O: 280.04

[0225] (3) Synthesis of Intermediate 32-3

[0226]

[0227] Under nitrogen atmosphere, 9-phenanthreneboric acid (30 g, 135.3 mmol), 1,4-dibromonaphthalene (43 g, 150 mmol), K 2 CO 3 (41.4 g, 300 mmol), Pd(PPh 3 ) 4 (8.6 g, 7.5 mmol) was placed in a four-necked reaction flask, and 225 mL of THF and 75 mL of H 2 After the reaction was completed, the reaction solution was cooled to room temperature, 300 mL of water was added, extracted with ethyl acetate, and purified by column chromatography (eluted with n-hexane) to obtain intermediate 32-3 (34 g, yield 59%).

[0228] LC-MS(APCI): 383.15(M+H+).Calcd for:C 24 H 15 Br:382.04

[0229] (4) Synthesis of Intermediate 32-4

[0230]

[0231] Under nitrogen atmosphere, intermediate 32-3 (30 g, 78.5 mmol) was placed in a four-necked reaction bottle, and then 300 mL of THF was added, the temperature was lowered to -78 ° C, and n-butyl lithium (38 mL, 94.2 mmol) was added dropwise. During the addition, the temperature was controlled not to be higher than -60 ° C. After the addition was completed, this temperature was maintained to continue the reaction for 2 h. Then the temperature was lowered to -78 ° C again, trimethyl borate (12 g, 117.7 mmol) was added dropwise, and after the addition was completed, the room temperature was slowly raised and stirred overnight. After the reaction was completed, 200 mL of 3 mol / L dilute hydrochloric acid was added and stirring was continued for 30 min. Then it was extracted with ethyl acetate, concentrated to dryness, and refluxed with n-hexane to obtain intermediate 32-4 (14 g, yield 52%).

[0232] LC-MS(APCI): 349.25(M+H+).Calcd for:C 24 H 17 BO 2 :348.13

[0233] (5) Synthesis of Compound 32

[0234]

[0235] Under nitrogen atmosphere, intermediate 32-2 (15 g, 53.3 mmol), intermediate 32-4 (22 g, 64 mmol), K 2 CO 3 (14.7 g, 106.6 mmol), Pd(PPh 3 ) 4 (3 g, 2.6 mmol) was placed in a four-necked reaction flask, and 112.5 mL of THF and 37.5 mL of H 2 The mixed solution of 1,2-dihydro-1,4-dihydro-2-nitropropene was heated to reflux for reaction. After the reaction was completed, the reaction solution was cooled to room temperature, and a large amount of white solid precipitated, which was directly filtered. The solid was slurried with 160 mL of ethyl acetate to obtain compound 32 (22 g, yield 75%).

[0236] LC-MS(APCI): 549.17(M+H+).Calcd for:C 40 H 24 N 2 O:548.19

[0237] 1HNMR (400MHz, CD 2 Cl 2)δ8.77(t,2H),8.45(d,1H),8.32(m,2H),8.19(d,1H),7.85-7.93(m,5H),7.81(s,1H),7.59-7.70(m,4H),7.36-7.51(m,7H),7.26(m,1H). Example 3: Synthesis of Compound 38

[0238] (1) Synthesis of Intermediate 38-1

[0239]

[0240] Yu N 2 atmosphere, compound A (120.0 g, 500 mmol), compound B (80.0 g, 360 mmol), NaHCO 3 (60.6 g, 572 mmol) and Pd(dppf)Cl 2 (2.6 g) was put into a four-necked flask, and a mixed solvent of toluene, water and ethanol (1080 mL: 360 mL: 60 mL) was added, and the temperature was raised to reflux for 4 h. After cooling, dichloromethane and water were extracted three times, and the organic phases were combined and dried by spin drying. Then, n-hexane column chromatography was used to obtain the intermediate 38-1 (85 g, yield 70%) as an off-white solid.

[0241] LC-MS(APCI): 339.83(M+H+).Calcd for: C 24 H 15 Cl:338.09

[0242] (2) Synthesis of Intermediate 38-2

[0243]

[0244] Yu N 2 atmosphere, intermediate 38-1 (80.0 g, 237 mmol), compound C (58.5 g, 230 mmol), CH 3 COOK (61.7 g, 630 mmol) and Pd(dppf)Cl 2 (3.0 g) was put into a four-necked bottle, and about 1 L of 1,4-dioxane was added. The system was heated to reflux for 4 h. After cooling, dichloromethane and water were extracted three times, and the organic phases were combined and dried by spin drying. Then, the intermediate 38-2 (80 g, yield 79%) was obtained as a white solid by n-hexane column chromatography.

[0245] LC-MS (APCI): 431.5 (M+H + ).Calcd for:C 30 H 27BO 2 :430.21

[0246] (3) Synthesis of intermediate 38-3

[0247]

[0248] Yu N 2 In the atmosphere, compound D (20.0 g, 108 mmol), compound E (80.0 g, 357 mmol) and 0.6 g of dibromohydantoin were put into a four-necked bottle and stirred. As the reaction proceeded, the system solidified after about 30 minutes. Dichloromethane and water were extracted, the organic phases were combined and spin-dried. Then, it was purified by silica gel chromatography (developing solvent was n-hexane: ethyl acetate volume ratio 3:1), and then slurried once with a mixed solution of n-hexane and dichloromethane (volume ratio 5:1) to obtain intermediate 38-3 (28 g, yield 96%) as an orange solid.

[0249] LC-MS (APCI) 274.24 (M+H + ).Calcd for:C 13 H 8 BrNO:272.98

[0250] (4) Synthesis of Intermediate 38-4

[0251]

[0252] Yu N 2 atmosphere, intermediate 38-3 (28.0 g, 102 mmol), formamide (18.4 g, 409 mmol), K 2 CO 3 (42.4g, 307mmol), Xantphos (5.8g) and Pd 2 (dba) 3 (1.9 g) was placed in a four-necked bottle, and about 1 L of 1,4-dioxane was added. The system was heated to reflux and kept warm overnight. After cooling, DCM and H 2 O was extracted three times, the organic phases were combined and dried. NaOH (12.3 g, 307 mmol) and 600 mL 1,4-dioxane were added to the crude product, stirred at 60 ° C for 2 h, and the heating was stopped after the reaction. After cooling, dichloromethane and water were extracted three times, the organic phases were combined and dried. Then, it was purified by silica gel chromatography (developing solvent: n-hexane: dichloromethane volume ratio 3:1) to obtain intermediate 38-4 (21 g, 98%) as a yellow solid.

[0253] LC-MS (APCI): 211.24 (M+H + ).Calcd for:C 13 H10 N 2 O:210.08

[0254] (5) Synthesis of Intermediate 38-5

[0255]

[0256] Yu N 2 atmosphere, intermediate 38-4 (21.0 g, 100 mmol), ethyl acrylate (12.0 g, 120 mmol), Na 2 S 2 O 8 (47.4 g, 200 mmol), p-toluenesulfonic acid monohydrate (19.0 g, 100 mmol) and 1.1 g Pd(AcO) 2 Put it into a four-necked bottle, add about 500 mL of toluene, heat it to reflux, and keep it warm overnight. After cooling, extract it three times with dichloromethane and water, combine the organic phases, and spin dry. Then purify it by silica gel chromatography (developing solvent is n-hexane: dichloromethane volume ratio 2:1) to obtain intermediate 38-5 (20 g, yield 76%) as a yellow solid.

[0257] LC-MS (APCI): 263.27 (M+H + ).Calcd for:C 16 H 10 N 2 O 2 :262.07

[0258] (6) Synthesis of Intermediate 38-6

[0259]

[0260]

[0261] Yu N 2 Atmosphere, intermediate 38-5 (20.0 g, 76 mmol) and SOCl 2 (27.2 g, 229 mmol) was put into a four-necked bottle, and about 300 mL of DMF was added. The temperature was raised to 80 ° C, and then the temperature was kept and stirred for 3 hours. The system gradually dissolved and became brown-red, and then the color of the system turned black. After cooling, dichloromethane and water were extracted, and the organic phases were combined and dried. Then it was purified by silica gel chromatography (developing solvent was n-hexane: dichloromethane volume ratio 3:1) to obtain white intermediate 38-6 (14 g, yield 66%).

[0262] LC-MS (APCI): 281.71 (M+H + ).Calcd for:C 16 H9 C1N 2 O:280.04

[0263] (7) Synthesis of Compound 38

[0264]

[0265] N 2 Under atmosphere, intermediate 38-2 (7.7 g, 18 mmol), intermediate 38-6 (5 g, 18 mmol), K 2 CO 3 (7.4 g, 54 mmol) and Pd(PPh 3 ) 4 (0.4g) was put into a four-necked flask, and a mixed solvent of 60mL toluene and 20mL water was added, and the temperature was raised to reflux, and then kept warm overnight. After cooling, dichloromethane and water were extracted three times, and the organic phases were combined and spin-dried. Qualified compound 38 (4.7g, yield 48%) was obtained by purification by silica gel column chromatography (developing solvent: n-hexane: dichloromethane volume ratio 3:1), and then recrystallization was performed using chlorobenzene.

[0266] LC-MS (APCI): 549.42 (M+H + ).Calcd for:C 40 H 24 N 2 O:548.19

[0267] 1H NMR (400MHz, CD 2 Cl 2 )δ8.82–8.72(m,2H),8.45(d,1H),8.32(dd,2H),8.24(d,1H),7.94–7.78(m,6H), 7.67(dd,2H),7.64–7.60(m,2H),7.50(dd,4H),7.45–7.38(m,3H),7.26(dd,1H).

[0268] Example 4: Synthesis of Compound 253

[0269]

[0270] Under nitrogen atmosphere, intermediate 32-2 (4.00 g, 14.25 mmol), raw material F (7.17 g, 15.67 mmol), tetrakis(triphenylphosphine)palladium (0.30 mg, 0.29 mmol) and potassium carbonate (3.93 g, 28.50 mmol) were placed in a 500 mL four-necked bottle, 30 mL of tetrahydrofuran and 10 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 5 h. After the reaction was completed, the heating was stopped and the product precipitated. A light yellow solid was obtained by filtration, and the filter cake was refluxed with 50 mL of ethyl acetate to obtain a white solid compound 253 (3.5 g, yield 43%).

[0271] LC-MS (APCI): 577.54 (M+H + ).Calcd for:C 40 H 24 N 4 O: 576.66

[0272] 1H NMR(400MHz,Methylene Chloride-d2)δ9.41(t,1H),8.62(ddd,1H),8.56(ddd,1H),8.54–8.48(m,3H),8. 47–8.35(m,5H),8.29(d,1H),8.21(d,1H),7.99–7.81(m,5H),7.67–7.44(m,6H).

[0273] The following application examples further illustrate the application of the organic electroluminescent material and the organic electroluminescent element comprising the same according to the present invention.

[0274] Application Example 1:

[0275] This embodiment provides an organic electroluminescent element, such as Figure 1 As shown, it includes a 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 stacked from bottom to top, wherein the hole injection layer 2, the hole transport layer 3, the light-emitting layer 4 and the electron transport layer 5 are the first light-emitting unit 100, and the hole transport layer 8, the light-emitting layer 9, the electron transport layer 10 and the electron injection layer 11 are the second light-emitting unit 200.

[0276] The specific device structure is:

[0277] 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).

[0278] Device preparation process:

[0279] 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.

[0280] Then put the bottom luminescent glass substrate into the evaporation chamber and place it in a vacuum chamber of about 10 -8 Each organic layer was deposited on the ITO first electrode in sequence by thermal vacuum evaporation at a rate of 0.2-2 angstroms / second under the condition of support. 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 main body 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 with a thickness of 20 nm as a hole transport layer. 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 second electrode.

[0281] 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 component 1.

[0282]

[0283] Contrast structure

[0284] Bphen(4,7-Diphenyl-1,10-phenanthroline)

[0285]

[0286] Examples and Comparative Examples

[0287] The N-type charge generation layer 6 was prepared by using the compound prepared in Example 1 of the present invention instead of the Bphen material, and the organic electronic element 2 was prepared by the same method.

[0288] The N-type charge generation layer 6 was prepared by using the compound obtained in Example 2 of the present invention instead of the Bphen material, and the organic electronic element 3 was prepared by the same method.

[0289] The N-type charge generation layer 6 was prepared by using the compound obtained in Example 3 of the present invention instead of the Bphen material, and the organic electronic element 4 was prepared by the same method.

[0290] The N-type charge generation layer 6 was prepared by using the compound obtained in Example 4 of the present invention instead of the Bphen material, and the organic electronic element 5 was prepared by the same method.

[0291] Organic electroluminescent element evaluation

[0292] 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.

[0293] Driving voltage and current efficiency at current density 15mA / cm 2 The above test results are shown in the following table:

[0294]

[0295] Compared with the organic electronic element 1 , the above organic electroluminescent elements 2 , 3 , and 5 have lower driving voltage, higher current efficiency, and longer service life. The organic electroluminescent element 4 has improved current efficiency and prolonged service life.

[0296] 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.

[0297] The above is a detailed introduction to an organic electroluminescent material and an organic electroluminescent element comprising the same provided by the present invention. 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, several improvements and modifications can be made to the present invention, and these improvements and modifications also fall within the scope of protection of the claims of the present invention.

Claims

1. An organic electroluminescent material, characterized in that The material has a structure shown in formula (1), in represents a double bond or a single bond, X 1 Selected from O, S, N, NR, X 2 is selected from O, S, N, and NR, R is selected from hydrogen, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, L 1 -L 4 are each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group, R 1 -R 4 Each is 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 C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl.

2. The organic electroluminescent material according to claim 1, characterized in that: The organic electroluminescent material is selected from one of the compounds represented by the following formula (1-1) and formula (1-2), X 1 , X 2 , L 1 -L 4 , R 1 -R 4 The same as defined in claim 1; Preferably, the organic electroluminescent material is selected from one of the compounds represented by the following formula (1-5) and formula (1-6), In formula (1-5) and (1-6), X 1 Select from O or S, X 2 Selected from O or S, L 1 , L 4 , R 1 , R 4 The same definition as claim 1; Most preferably, the organic electroluminescent material is selected from one of the compounds represented by the following formula (1-3) and formula (1-4), In formula (1-3) and (1-4), X 1 Select from O or S, X 2 Selected from O or S, L 1 , R 1 The definition is the same as that of claim 1.

3. The organic electroluminescent material according to claim 2, characterized in that: In the formula (1-3), L 1 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group, R 1 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 C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; And / or, in the formula (1-4), L 1 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group, R 1 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 C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; And / or, in the formula (1-5), L 1 Selected from single bonds, R 1 is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, L 4 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, R 4 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 C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; And / or, in the formula (1-6), L 1 Selected from single bonds, R 1 is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, L 4 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, R 4 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 C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.

4. The organic electroluminescent material according to any one of claims 2 to 3, characterized in that: In the formula (1-5), R 1 , R 4 At least one of Where R 10 -R 19 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, R 10 -R 19 Each exists independently or R 10 -R 19 Two adjacent rings may be connected to each other to form a ring C, wherein the ring C is selected from a substituted or unsubstituted C3-C30 ring, Preferably, X 2 Selected from O; And / or, in the formula (1-6), R 1 , R 4 At least one of Where R 10 -R 19 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, R 10 -R 19 Each exists independently or R 10 -R 19 Two adjacent rings may be connected to each other to form a ring C, wherein the ring C is selected from a substituted or unsubstituted C3-C30 ring, Preferably, X 1 Selected from O.

5. The organic electroluminescent material according to any one of claims 2 to 3, characterized in that: In the formula (1-5), R 1 , R 4 At least one of Where R 21 -R 28 is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, Preferably, X 2 Selected from O; And / or, in the formula (1-6), R 1 , R 4 At least one of Where R 21 -R 28 is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, Preferably, X 1 Selected from O.

6. The organic electroluminescent material according to claim 1, characterized in that: The organic electroluminescent material has a structure shown in formula (1-7), L 1 -L 5 are each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group, R 1 -R 5 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 C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, In the “substituted or unsubstituted”, the substituents when substituted are each independently selected from deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C3-C30 heteroaryl, C6-C30 aryl, and C7-C30 aralkyl.

7. The organic electroluminescent material according to claim 1, characterized in that The organic electroluminescent material is selected from any one of the following compounds No. 1 to 281:

8. An organic light-emitting element, characterized in that: include: a first electrode; a second electrode; and at least two light-emitting units, wherein a charge generation layer is provided between the light-emitting units, and the charge generation layer comprises the organic electroluminescent material according to any one of claims 1 to 7.

9. The organic electroluminescent element according to claim 8, characterized in that: The charge generation layer between the two light emitting units comprises an N-type charge generation layer and a P-type charge generation layer, wherein the N-type charge generation layer comprises the organic electroluminescent material according to any one of claims 1 to 7.

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 8 or 9.

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