Boron-containing resonance type organic compound and organic electroluminescent device containing same

Abstract

The invention relates to a boron-containing resonance type organic compound and an organic light-emitting device containing the same, and belongs to the technical field of semiconductors, and the structure of the compound provided by the invention is as shown in a general formula (1): # imgabs0. The compound provided by the invention is used as a doping material in a light-emitting layer material of an OLED (Organic Light-Emitting Diode) light-emitting device; the material can be used as a luminescent layer green light doping material of an organic electroluminescent device, so that the service life of the device is prolonged.

Description

Technical Field

[0001] The present invention relates to the field of semiconductor technology, and in particular to a boron-containing resonance-type organic compound and an organic electroluminescent device containing the same. Background Art

[0002] Compared with liquid crystal display (LCD), organic light-emitting diode (OLED) has technical advantages such as lighter and thinner, high color contrast, low power consumption, fast response, high clarity, and flexibility, and is believed to dominate future display terminal products. With the advent of the 5G era, the new information display industry is in urgent need of iterative development. The early lower color gamut standards (BT.709 and DCIP3) can no longer meet the high-quality technical development needs of display products. In order to achieve the performance requirements of ultra-high definition and higher picture quality of display products, the new generation of display standards (BT.2020) drives OLED luminescent materials to develop towards high color purity, which requires the core luminescent materials to have a narrower emission spectrum. Among the three commercialized OLED red, green and blue color rendering technologies, blue light uses traditional fluorescent triplet-triplet conversion (TTF) technology, which has low efficiency but high color purity and basically meets the BT.2020 display indicators; green and red light use phosphorescence technology, which has high efficiency. Red light is close to the BT.2020 display indicators, while green light is limited by the wider emission spectrum of phosphorescence, which is quite different from the requirements of high-definition display indicators. Therefore, it is very critical to develop high-color-purity green light OLED materials.

[0003] Since 2020, green light materials with narrow half-width (half-width <30nm) based on boron-nitrogen resonance structures have been reported one after another: DOI:10.1002 / adom.201902142, DOI:10.1002 / anie.202008264, DOI:10.1021 / jacs.0c10081, DOI:10.1038 / s41467-022-32607-3, DOI:10.1002 / anie.202202380, etc., showing the extremely high color purity and efficiency of this type of material, becoming the development trend of high color purity green light OLEDs. However, there are still many technical difficulties in the development of green light ultra-high color purity materials containing boron and nitrogen structures. The existing materials also have the defects that their efficiency and lifespan cannot meet the needs of mass production. The development of narrow half-width green light materials based on boron and nitrogen resonance structures that can meet practical applications is a key technical point for the next generation of high color purity, high color gamut coverage, high efficiency and high immersion display devices.

[0004] In addition, the sensitization technology combines triplet exciton-sensitizing materials (including but not limited to TADF materials and phosphorescent materials) with fluorescent doping materials, utilizes triplet exciton-sensitizing materials as exciton-sensitizing media, fully utilizes triplet excitons, and transfers energy to fluorescent doping materials through energy transfer, which can also achieve 100% device internal quantum efficiency. This technology can make up for the shortcomings of insufficient exciton utilization of fluorescent doping materials, and effectively give play to the characteristics of high fluorescence quantum yield, high device stability, high color purity and low price of fluorescent doping materials, and has broad prospects in OLEDs applications. For example, CN107507921A and CN110492006A disclose a luminescent layer combination technology with TADF materials with a difference of the lowest singlet and triplet energy levels of less than or equal to 0.2eV as the main body and boron-containing materials as doping; CN110492005A and CN110492009A disclose a luminescent layer combination scheme with an exciplex as the main body and boron-containing materials as doping; both can achieve efficiency comparable to phosphorescence and a relatively narrow half-width. Therefore, the development of sensitization technology based on narrow half-width boron-based luminescent materials has unique advantages and strong potential in terms of BT.2020 display indicators. Summary of the invention

[0005] In view of the above problems existing in the prior art, the present invention provides a boron-containing resonance-type organic compound and an organic electroluminescent device comprising the same. The compound of the present invention is used as a doping material for the light-emitting layer of the organic electroluminescent device to emit green light.

[0006] The technical solution of the present invention is as follows: a boron-containing resonance type organic compound, the structure of the boron-containing resonance type organic compound is shown in the general formula (1):

[0007]

[0008] In the general formula (1), R 1 , R 2 Each occurrence of the same or different radicals represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a C substituted or unsubstituted with a substituent. 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 2 ~C 10 Alkynyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 5 ~C 10aryloxy, arylamine substituted or unsubstituted by substituents, C 6 ~C 30 An aryl group, a 5-30 membered heteroaryl group which may be substituted by a substituent or not, or a borane group which may be substituted by a substituent or not;

[0009] R 1 and R 2 Can be connected to a substituted or unsubstituted C 6 ~C 30 Aromatic ring, 5-30 membered heteroaromatic ring substituted or unsubstituted by substituents, C 5 ~C 30 aliphatic ring;

[0010] Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 Each occurrence is independently represented by N, CH or CR a ; R a Deuterium atom, halogen atom, cyano group, substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 2 ~C 10 Alkynyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 5 ~C 10 aryloxy, arylamine substituted or unsubstituted by substituents, C 6 ~C 30 One of an aryl group, a 5-30-membered heteroaryl group which may be substituted by a substituent, and a borane group which may be substituted by a substituent;

[0011] Ar 1 ,Ar 2 Each occurrence of the same or different atoms represents a hydrogen atom, a deuterium atom, a halogen atom, a C substituted or unsubstituted with a substituent. 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C2 ~C 10 Alkenyl, substituted or unsubstituted C 2 ~C 10 Alkynyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 5 ~C 10 aryloxy, arylamine substituted or unsubstituted by substituents, C 6 ~C 30 An aryl group, a 5-30 membered heteroaryl group which may be substituted by a substituent or not, or a borane group which may be substituted by a substituent or not;

[0012] Each occurrence of M1, M2, M3, and M4 is the same or different and represents C substituted or unsubstituted by one or more R 6 ~C 30 An aromatic ring, a 5-30 membered heteroaromatic ring substituted or unsubstituted by one or more R;

[0013] Each occurrence of R, which is the same or different, represents a deuterium atom, a tritium atom, a halogen atom, a cyano group, a C substituted or unsubstituted group. 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 2 ~C 10 Alkynyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 5 ~C 10 aryloxy, arylamine substituted or unsubstituted by substituents, C 6 ~C 30 One of an aryl group, a 5-30-membered heteroaryl group which may be substituted by a substituent, and a borane group which may be substituted by a substituent;

[0014] The substitution mode of R is a single bond or a ring connection;

[0015] Each occurrence of X, whether the same or different, represents a carbon atom or a silicon atom;

[0016] The substituents are selected from deuterium, tritium, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, deuterium or tritium substituted C 1 ~C10 Alkyl, C 3 ~C 10 Cycloalkyl, C 6 ~C 30 Aryl, deuterium or tritium substituted C 6 ~C 30 Any one or more of aryl, 5-30 membered heteroaryl, deuterium or tritium substituted 5-30 membered heteroaryl;

[0017] The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

[0018] Furthermore, the structure of the boron-containing resonance-type organic compound is shown in general formula (A):

[0019]

[0020] In the general formula (A), R 1 ~R 12 Each occurrence independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a C 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 2 ~C 10 Alkynyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 5 ~C 10 aryloxy, arylamine substituted or unsubstituted by substituents, C 6 ~C 30 An aryl group, a 5-30 membered heteroaryl group which may be substituted by a substituent or not, or a borane group which may be substituted by a substituent or not;

[0021] R 1 ~R 12 Any two adjacent groups can be connected to form a C substituted or unsubstituted 6 ~C 30 Aromatic ring, 5-30 membered heteroaromatic ring substituted or unsubstituted by substituents, C 5 ~C 30 aliphatic ring;

[0022] Z 1 , Z 2 , Z 3 , Z4 , Z 5 , Z 6 Each occurrence is independently represented by N, CH or CR a ; R a Deuterium atom, halogen atom, cyano group, substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 2 ~C 10 Alkynyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 5 ~C 10 aryloxy, arylamine substituted or unsubstituted by substituents, C 6 ~C 30 One of an aryl group, a 5-30-membered heteroaryl group which may be substituted by a substituent, and a borane group which may be substituted by a substituent;

[0023] Ar 1 ,Ar 2 Each occurrence of the same or different atoms represents a hydrogen atom, a deuterium atom, a halogen atom, a C substituted or unsubstituted with a substituent. 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 2 ~C 10 Alkynyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 5 ~C 10 aryloxy, arylamine substituted or unsubstituted by substituents, C 6 ~C 30 An aryl group, a 5-30 membered heteroaryl group which may be substituted by a substituent or not, or a borane group which may be substituted by a substituent or not;

[0024] Each occurrence of M1, which is the same or different, represents C substituted or unsubstituted by one or more R 6 ~C 30An aromatic ring, a 5-30 membered heteroaromatic ring substituted or unsubstituted by one or more R;

[0025] Each occurrence of R, which is the same or different, represents a deuterium atom, a tritium atom, a halogen atom, a cyano group, a C substituted or unsubstituted group. 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 2 ~C 10 Alkynyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 5 ~C 10 aryloxy, arylamine substituted or unsubstituted by substituents, C 6 ~C 30 One of an aryl group, a 5-30-membered heteroaryl group which may be substituted by a substituent, and a borane group which may be substituted by a substituent;

[0026] The substitution mode of R is a single bond or a ring connection;

[0027] Each occurrence of X, whether the same or different, represents a carbon atom or a silicon atom;

[0028] The substituents are selected from deuterium, tritium, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, deuterium or tritium substituted C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 6 ~C 30 Aryl, deuterium or tritium substituted C 6 ~C 30 Any one or more of aryl, 5-30 membered heteroaryl, deuterium or tritium substituted 5-30 membered heteroaryl;

[0029] The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

[0030] Furthermore, the structure of the boron-containing resonance-type organic compound is as shown in any one of the general formulas (A-1) to (A-4):

[0031]

[0032] In the general formulas (A-1) to (A-4), R1 ~R 12 ,Ar 1 ,Ar 2 , X, Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 The definition of is the same as that in the general formula (A);

[0033] Z, Z 7 , Z 8 , Z 9 , Z 10 , Z 11 Each occurrence is independently represented by N, CH or CR a ; R a Deuterium atom, halogen atom, cyano group, substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 2 ~C 10 Alkynyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 5 ~C 10 aryloxy, arylamine substituted or unsubstituted by substituents, C 6 ~C 30 One of an aryl group, a 5-30-membered heteroaryl group which may be substituted by a substituent, and a borane group which may be substituted by a substituent;

[0034] Y represents O, S, NR 13 or C(R 14 )(R 15 );

[0035] R 13 It is represented by a C substituted or unsubstituted 6 ~C 30 Aryl, or one of 5-30 heteroaryl groups which may be substituted by a substituent or unsubstituted;

[0036] R 14 , R 15 It is represented by a C substituted or unsubstituted 1 ~C 10 Alkyl, substituted or unsubstituted C6 ~C 30 Aryl, 5-30 membered heteroaryl which may be substituted by a substituent;

[0037] Ar 3 ,Ar 4 Each occurrence independently represents a hydrogen atom, a deuterium atom, a halogen atom, a C 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 2 ~C 10 Alkynyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 5 ~C 10 aryloxy, arylamine substituted or unsubstituted by substituents, C 6 ~C 30 An aryl group, a 5-30 membered heteroaryl group which may be substituted by a substituent or not, or a borane group which may be substituted by a substituent or not;

[0038] The substituents are selected from deuterium, tritium, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, deuterium or tritium substituted C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 6 ~C 30 Aryl, deuterium or tritium substituted C 6 ~C 30 Any one or more of aryl, 5-30 membered heteroaryl, deuterium or tritium substituted 5-30 membered heteroaryl;

[0039] The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

[0040] Furthermore, the structure of the boron-containing resonance-type organic compound is as shown in any one of the general formulas (A-5) to (A-8):

[0041]

[0042] In the general formulas (A-5) to (A-8), R 1 ~R 12 ,Ar 1 ,Ar2 , Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 The definition of is the same as that in the general formula (A);

[0043] Z, Z 7 , Z 8 , Z 9 , Z 10 , Z 11 Each occurrence is independently represented by N, CH or CR a ; R a Deuterium atom, halogen atom, cyano group, substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 2 ~C 10 Alkynyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 5 ~C 10 aryloxy, arylamine substituted or unsubstituted by substituents, C 6 ~C 30 One of an aryl group, a 5-30-membered heteroaryl group which may be substituted by a substituent, and a borane group which may be substituted by a substituent;

[0044] R 13 It is represented by a C substituted or unsubstituted 6 ~C 30 Aryl, or one of 5-30 heteroaryl groups which may be substituted by a substituent or unsubstituted;

[0045] Ar 3 ,Ar 4 Each occurrence independently represents a hydrogen atom, a deuterium atom, a halogen atom, a C 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 2 ~C 10Alkynyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 5 ~C 10 aryloxy, arylamine substituted or unsubstituted by substituents, C 6 ~C 30 An aryl group, a 5-30 membered heteroaryl group which may be substituted by a substituent or not, or a borane group which may be substituted by a substituent or not;

[0046] The substituents are selected from deuterium, tritium, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, deuterium or tritium substituted C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 6 ~C 30 Aryl, deuterium or tritium substituted C 6 ~C 30 Any one or more of aryl, 5-30 membered heteroaryl, deuterium or tritium substituted 5-30 membered heteroaryl;

[0047] The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

[0048] Furthermore, the structure of the boron-containing resonance-type organic compound is as shown in any one of the general formulas (A-9) to (A-12):

[0049]

[0050] In the general formulas (A-9) to (A-12), R 3 ~R 12 ,Ar 1 ,Ar 2 , Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 The definition of is the same as that in the general formula (A);

[0051] Z, Z 7 , Z 8 , Z 9 , Z 10 , Z 11 Each occurrence is independently represented by N, CH or CR a ; R a Deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 2 ~C 10 Alkynyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 5 ~C 10 aryloxy, arylamine substituted or unsubstituted by substituents, C 6 ~C 30 One of an aryl group, a 5-30-membered heteroaryl group which may be substituted by a substituent, and a borane group which may be substituted by a substituent;

[0052] R 13 It is represented by a C substituted or unsubstituted 6 ~C 30 Aryl, or one of 5-30 heteroaryl groups which may be substituted by a substituent or unsubstituted;

[0053] Ar 3 ,Ar 4 Each occurrence independently represents a hydrogen atom, a deuterium atom, a halogen atom, a C 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 2 ~C 10 Alkynyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 5 ~C 10 aryloxy, arylamine substituted or unsubstituted by substituents, C 6 ~C 30 An aryl group, a 5-30 membered heteroaryl group which may be substituted by a substituent or not, or a borane group which may be substituted by a substituent or not;

[0054] The substituents are selected from deuterium, tritium, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, deuterium or tritium substituted C 1 ~C10 Alkyl, C 3 ~C 10 Cycloalkyl, C 6 ~C 30 Aryl, deuterium or tritium substituted C 6 ~C 30 Any one or more of aryl, 5-30 membered heteroaryl, deuterium or tritium substituted 5-30 membered heteroaryl;

[0055] The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

[0056] Furthermore, the structure of the boron-containing resonance-type organic compound is as shown in any one of the general formulas (A-13) to (A-16):

[0057]

[0058] In the general formulas (A-13) to (A-16), R a , R 8 , R 11 ,Ar 1 ,Ar 2 , X, Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 The definition of is the same as that in the general formula (A);

[0059] R 13 It is represented by a C substituted or unsubstituted 6 ~C 30 Aryl, or one of 5-30 heteroaryl groups which may be substituted by a substituent or unsubstituted;

[0060] Ar 3 ,Ar 4 Each occurrence independently represents a hydrogen atom, a deuterium atom, a halogen atom, a C 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 2 ~C 10 Alkynyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 5 ~C 10aryloxy, arylamine substituted or unsubstituted by substituents, C 6 ~C 30 An aryl group, a 5-30 membered heteroaryl group which may be substituted by a substituent or not, or a borane group which may be substituted by a substituent or not;

[0061] The substituents are selected from deuterium, tritium, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, deuterium or tritium substituted C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 6 ~C 30 Aryl, deuterium or tritium substituted C 6 ~C 30 Any one or more of aryl, 5-30 membered heteroaryl, deuterium or tritium substituted 5-30 membered heteroaryl;

[0062] The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

[0063] Further, the M1, M2, M3, and M4 represent any one of the following groups substituted or unsubstituted by R: phenyl, naphthyl, anthracenyl, phenanthrenyl, pyridyl, quinolyl, furyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, indole[3,2,1-jk]carbazolyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and spirofluorenyl;

[0064] The R, R arepresented by a deuterium atom, a halogen atom, a cyano group, a methyl group which may be substituted by a substituent, an ethyl group which may be substituted by a substituent, an isopropyl group which may be substituted by a substituent, a tert-butyl group which may be substituted by a substituent, a cyclohexyl group which may be substituted by a substituent, an adamantyl group which may be substituted by a substituent, a phenyl group which may be substituted by a substituent, a biphenyl group which may be substituted by a substituent, a terphenyl group which may be substituted by a substituent, a naphthyl group which may be substituted by a substituent, an anthracenyl group which may be substituted by a substituent, a phenanthryl group which may be substituted by a substituent, a pyridyl group which may be substituted by a substituent, and a quinolyl group which may be substituted by a substituent , a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted amino group, and a substituted or unsubstituted triazinyl group;

[0065] The R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12Each of the above is independently a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a methyl group which may be substituted or unsubstituted, an ethyl group which may be substituted or unsubstituted, an isopropyl group which may be substituted or unsubstituted, a tert-butyl group which may be substituted or unsubstituted, a cyclohexyl group which may be substituted or unsubstituted, an adamantyl group which may be substituted or unsubstituted, a phenyl group which may be substituted or unsubstituted, a biphenyl group which may be substituted or unsubstituted, a terphenyl group which may be substituted or unsubstituted, a naphthyl group which may be substituted or unsubstituted, an anthracenyl group which may be substituted or unsubstituted, a phenanthrenyl group which may be substituted or unsubstituted, a pyridyl group which may be substituted or unsubstituted, unsubstituted quinolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazinyl;

[0066] The Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 wherein each independently represents a methyl group substituted or unsubstituted by a substituent, an ethyl group substituted or unsubstituted by a substituent, an isopropyl group substituted or unsubstituted by a substituent, a tert-butyl group substituted or unsubstituted by a substituent, a cyclohexyl group substituted or unsubstituted by a substituent, an adamantyl group substituted or unsubstituted by a substituent, a phenyl group substituted or unsubstituted by a substituent, a biphenyl group substituted or unsubstituted by a substituent, a terphenyl group substituted or unsubstituted by a substituent, a naphthyl group substituted or unsubstituted by a substituent, an anthracenyl group substituted or unsubstituted by a substituent, a phenanthrenyl group substituted or unsubstituted by a substituent, a pyridyl group substituted or unsubstituted by a substituent, a quinolyl group substituted or unsubstituted by a substituent, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted amino group, and a substituted or unsubstituted triazinyl group;

[0067] The R 13 substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzofuranyl ... substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted N-phenylcarbazolyl group, substituted or unsubstituted 9,9-dimethylfluorenyl group, substituted or unsubstituted 9,9-diphenylfluorenyl group, substituted or unsubstituted spirofluorenyl group, substituted or unsubstituted amino group, substituted or unsubstituted triazinyl group;

[0068] The R 14 , R 15 represented by a methyl group substituted or unsubstituted by a substituent, an ethyl group substituted or unsubstituted by a substituent, an isopropyl group substituted or unsubstituted by a substituent, a tert-butyl group substituted or unsubstituted by a substituent, a cyclohexyl group substituted or unsubstituted by a substituent, an adamantyl group substituted or unsubstituted by a substituent, a phenyl group substituted or unsubstituted by a substituent, a biphenyl group substituted or unsubstituted by a substituent, a terphenyl group substituted or unsubstituted by a substituent, a naphthyl group substituted or unsubstituted by a substituent, an anthracenyl group substituted or unsubstituted by a substituent, a phenanthrenyl group substituted or unsubstituted by a substituent, a pyridyl group substituted or unsubstituted by a substituent, a quinolyl group substituted or unsubstituted by a substituent, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazinyl;

[0069] The substituents may be selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furanyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazoline group, and an azaphenanthryl group.

[0070] Further, the M1, M2, and M3 are represented by any of the following ring structures:

[0071]

[0072] The M4 is represented by any of the following ring structures:

[0073]

[0074] Y represents O, S, NR 13 or C(R 14 )(R 15 );

[0075] R 13 It is represented by phenyl;

[0076] R 14 , R 15 It is represented by methyl or phenyl;

[0077] Each occurrence of Z is independently represented by N, CH or CR a ;

[0078] The R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 They are independently represented as follows:

[0079] Hydrogen atom, deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano, trifluoromethyl, Any of;

[0080] The R, R aThey are independently represented as follows:

[0081] Deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano, trifluoromethyl, Any of;

[0082] The Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 It is represented by the following structure:

[0083] Methyl, isopropyl, tert-butyl, Any one of.

[0084] Furthermore, the specific structural formula of the boron-containing resonance-type organic compound is any one of the following structures:

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098] The present invention also provides an organic light-emitting device, which comprises a substrate, a first electrode, a second electrode and a functional layer in sequence, wherein the functional layer is located between the first electrode and the second electrode, and the functional layer comprises the boron-containing resonance-type organic compound described above in the present invention.

[0099] Preferably, the functional layer comprises a light-emitting layer, the light-emitting layer comprises a main material and a doping material, and the doping material is the boron-containing resonance-type organic compound described above in the present invention.

[0100] Preferably, the functional layer comprises a light-emitting layer, and the light-emitting layer comprises a first main material, a second main material and a doping material, at least one of the first main material and the second main material is a TADF material, and the doping material is the boron-containing resonance-type organic compound described above in the present invention.

[0101] Furthermore, the functional layer comprises a light-emitting layer, and the light-emitting layer comprises a main material, an exciton-sensitizing material and a doping material. The exciton-sensitizing material is a complex containing a metal element, and the doping material is the boron-containing resonance-type organic compound described above in the present invention.

[0102] Compared with the prior art, the beneficial technical effects of the present invention are:

[0103] (1) The compounds of the present invention are applied to OLED devices and can be used as doping materials for light-emitting layer materials. They can emit green fluorescence under the action of an electric field and can be applied to OLED lighting or OLED display fields;

[0104] (2) The compound of the present invention is used as a doping material and introduced into a phosphorescent sensitizer, which can effectively improve the efficiency and life of the device;

[0105] (3) The spectral FWHM of the compound of the present invention is relatively narrow, which can effectively improve the color gamut of the device and enhance the luminous efficiency of the device;

[0106] (4) The compound of the present invention is used as a doping material, and the TADF sensitizer is introduced as a second host, which can effectively improve the device efficiency;

[0107] The compound of the invention has a narrow half-peak width characteristic and can be used as a green light doping material of a light-emitting layer of an organic electroluminescent device, thereby improving the efficiency and life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0108] Figure 1 This is a schematic diagram of the structure of an OLED device in which the materials listed in the present invention are applied;

[0109] Among them, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer; DETAILED DESCRIPTION

[0110] The present invention is described in detail below in conjunction with the accompanying drawings and embodiments.

[0111] In the present invention, when describing electrodes and organic electroluminescent devices, as well as other structures, the words "upper", "lower", "top" and "bottom" used to indicate orientation only indicate the orientation in a certain state, and do not mean that the related structure can only exist in the orientation described; on the contrary, if the structure can change its position, such as inverted, the orientation of the structure will be changed accordingly. Specifically, in the present invention, the "bottom" or "lower" side of the electrode refers to the side of the electrode close to the substrate during the preparation process, and the opposite side away from the substrate is the "top" or "upper" side.

[0112] In the present invention, the aromatic amine group substituted or unsubstituted by a substituent group refers to Where Q 1 , Q 2 represents an aromatic group which may be substituted or unsubstituted by a substituent, Q 1 , Q 2 Preferably, it is represented by C substituted or unsubstituted with a substituent 6 -C 30 Aryl or 5- to 30-membered heteroaryl which may be substituted by a substituent.

[0113] In the present invention, C substituted or unsubstituted by a substituent 6 -C 30 The aryl group refers to phenyl which may be substituted by a substituent, naphthyl which may be substituted by a substituent, anthracenyl which may be substituted by a substituent, fluorenyl which may be substituted by a substituent, dimethylfluorenyl which may be substituted by a substituent, diphenylfluorenyl which may be substituted by a substituent, spirofluorenyl which may be substituted by a substituent, phenanthrenyl which may be substituted by a substituent, tetraphenyl which may be substituted by a substituent, pyrenyl which may be substituted by a substituent, biphenyl which may be substituted by a substituent, p-terphenyl which may be substituted by a substituent, m-terphenyl which may be substituted by a substituent, The invention also includes, but is not limited to, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted indenyl group, a combination thereof, or a condensed ring of a combination of the foregoing groups.

[0114] In the present invention, the 5-30 membered heteroaryl group substituted or unsubstituted by a substituent group refers to a furyl group substituted or unsubstituted by a substituent group, a thienyl group substituted or unsubstituted by a substituent group, a pyrrolyl group substituted or unsubstituted by a substituent group, a pyrazolyl group substituted or unsubstituted by a substituent group, an imidazolyl group substituted or unsubstituted by a substituent group, a triazolyl group substituted or unsubstituted by a substituent group, an oxazolyl group substituted or unsubstituted by a substituent group, a thiazolyl group substituted or unsubstituted by a substituent group, an oxadiazolyl group substituted or unsubstituted by a substituent group, a thiadiazolyl group substituted or unsubstituted by a substituent group, a pyridyl group substituted or unsubstituted by a substituent group, a pyrimidinyl group substituted or unsubstituted by a substituent group, a pyrazinyl group substituted or unsubstituted by a substituent group, a triazinyl group substituted or unsubstituted by a substituent group, a benzofuranyl group substituted or unsubstituted by a substituent group, a benzothiophenyl group substituted or unsubstituted by a substituent group, The present invention may include a substituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenathiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a combination thereof, or a condensed ring of a combination of the foregoing groups, but is not limited thereto.

[0115] The C of the present invention 1 -C 10 Alkyl (including straight-chain alkyl and branched alkyl) refers to methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl and the like, but is not limited thereto.

[0116] The C of the present invention 3 -C 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group containing 3 to 10 carbon atoms as ring atoms. 4 -C 9 Cycloalkyl, more preferably C 5 -C 8 Cycloalkyl, particularly preferably C 5 -C 7 Cycloalkyl. Non-limiting examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, cycloheptyl, and the like, but are not limited thereto.

[0117] The halogen atom mentioned in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0118] The C of the present invention 1 -C 10 The alkoxy group refers to a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an isopropoxy group or the like, but is not limited thereto.

[0119] The C of the present invention 2 -C 10 Alkenyl refers to vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1,1-dimethylallyl, 1-methylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl and 3-phenyl-1-butenyl, etc., but is not limited thereto.

[0120] The substituents may be selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furanyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthryl group.

[0121] As the substrate of the organic electroluminescent device of the present invention, any substrate commonly used in organic electroluminescent devices can be used. Examples are transparent substrates such as glass or transparent PI film substrates; opaque substrates such as silicon substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Depending on the properties of the substrate, its use direction is different. In the present invention, a transparent PI film substrate is preferably used. The thickness of the substrate is not particularly limited.

[0122] A first electrode is formed on a substrate, and the first electrode and the second electrode may be opposite to each other. The first electrode may be an anode. The first electrode may be a transmissive electrode, a semi-transmissive electrode or a reflective electrode. When the first electrode is a transmissive electrode, it may be formed using a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO) or indium tin zinc oxide (ITZO). When the first electrode is a semi-transmissive electrode or a reflective electrode, it may include metals such as Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir or Cr, or an alloy of several metals, or a combination of metals, metal oxides and metal alloys. The thickness of the first electrode layer depends on the material used, and is typically 50-500 nm, preferably 70-300 nm and more preferably 100-200 nm.

[0123] The organic functional material layer disposed between the first electrode and the second electrode includes, from bottom to top, a hole transport region, a light emitting layer and an electron transport region.

[0124] In the present invention, the hole transport region constituting the organic electroluminescent device can be exemplified by a hole injection layer, a hole transport layer, an electron blocking layer, and the like.

[0125] As the material for the hole injection layer, the hole transport layer, and the electron blocking layer, any material can be selected from known related materials used for organic electroluminescent devices.

[0126] The hole injection layer contains a main organic material that can conduct holes, and also contains a P-type dopant material with a deep HOMO energy level (the corresponding LUMO energy level will also be very deep). Based on empirical summary, in order to achieve smooth injection of holes from the anode to the organic film layer, the HOMO energy level of the main organic material that conducts holes used in the anode interface buffer layer must have certain characteristics with the P-doped material, so that the charge transfer state between the main material and the dopant material can be realized, the ohmic contact between the buffer layer and the anode can be achieved, and the efficient injection from the electrode to the hole injection conduction can be achieved.

[0127] In view of the above empirical summary, for hole-type host organic materials with different HOMO energy levels, different P-doped materials need to be selected to match them in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0128] Preferably, the main organic material of the hole injection layer of the present invention can be selected from the compounds disclosed in the following prior arts: JP1996048656A, JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, CN105439999A or CN103108859A.

[0129] Preferably, the P-type doping material is selected from the compounds with charge conductivity disclosed in the prior art, and the P-type dopant can be selected from the compounds disclosed in any one of the following documents: WO2011073149A, EP1968131A1, EP2276085A1, EP2213662A1, EP1722602A1, EP2045848A1, DE10200703122 0A1, US20100181555A1, US20100102709A1, WO2009003455A1, WO2010094378A1, WO2011120709A1, US20100096600A1, DE102012209523A1, CN101728485A and WO2012095143A1, but are not limited thereto.

[0130] In one embodiment of the present invention, the hole injection layer comprises a P-type dopant material with charge conductivity selected from the following: quinone derivatives, such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives, such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN); or cyclopropane derivatives, such as 4,4',4"-((1E,1'E,1"E)-cyclopropane-1,2,3-trimethylenetris(cyanoformyl))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited to these.

[0131] In the hole injection layer of the present invention, the ratio of the hole transport material to the P-type doping material used is 99:1-95:5, preferably 99:1-97:3, based on mass.

[0132] The thickness of the hole injection layer of the present invention may be 5-100 nm, preferably 5-50 nm, and more preferably 5-20 nm, but the thickness is not limited to this range.

[0133] Preferably, the hole transport layer material of the present invention may be selected from the following compounds disclosed in the prior art:

[0134] JP1996048656A, JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, CN103108859A.

[0135] Preferably, the hole transport layer material and the host organic material in the hole injection layer of the present invention are selected from the same compound.

[0136] The thickness of the hole transport layer of the present invention may be 5-200 nm, preferably 10-150 nm, and more preferably 20-100 nm, but the thickness is not limited to this range.

[0137] In one embodiment of the present invention, the electron blocking layer material of the present invention may be selected from the following compounds disclosed in the prior art:

[0138] CN102046613A, CN105408448A, KR1020160049955A, CN103108859A, KR1020130106255A, EP2922932A1, CN102224150A, US20170018710A1.

[0139] The thickness of the electron blocking layer of the present invention may be 1-50 nm, preferably 5-40 nm, but the thickness is not limited to this range.

[0140] After forming the hole injection layer, the hole transport layer and the electron blocking layer, a corresponding light emitting layer is formed on the electron blocking layer.

[0141] The light-emitting layer may include a host material and a dopant material. The host material may be a common green light host material in the art, and the dopant material may be a boron-containing resonance-type organic compound represented by the general formula (1) of the present invention.

[0142] The light-emitting layer may contain a single host material or a dual host material;

[0143] The dual-host material comprises a first host material and a second host material, and preferably at least one of the first host material and the second host material is a TADF material;

[0144] TADF materials refer to materials with thermally activated delayed fluorescence properties, characterized by a small energy level difference between the first excited singlet state and the first excited triplet state, so that the singlet excitons and triplet excitons generated can be used simultaneously in the device, making the utilization rate of the excitons generated by the device as close to 100% as possible. Compared with traditional fluorescent materials, TADF materials have a higher exciton utilization rate.

[0145] The light-emitting layer may include a host material, an exciton-sensitizing material, and a doping material;

[0146] Exciton sensitizing materials refer to materials that can make the luminescent material in the luminescent layer fully utilize the electroexcitons, so that the luminescent layer finally produces the emission spectrum of the sensitized material. Exciton sensitizers may undertake functions such as exciton capture, exciton conversion, and exciton transfer in electroluminescent devices. The boron-containing resonance-type organic compound represented by the general formula (1) of the present invention and the exciton sensitizing material are used in combination, which has a significant improvement effect on the problems of device efficiency improvement, exciton annihilation in the device, and efficiency reduction.

[0147] In the light-emitting layer of the present invention, the ratio of the host material to the doping material used is 99:1-70:30, preferably 99:1-85:15 and more preferably 97:3-87:13, based on mass.

[0148] The thickness of the light-emitting layer can be adjusted to optimize the light-emitting efficiency and the driving voltage. The preferred thickness range is 5 nm to 50 nm, more preferably 10-50 nm, and more preferably 15-40 nm, but the thickness is not limited to this range.

[0149] In the present invention, the electron transport region may include, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer disposed on the light emitting layer, but is not limited thereto.

[0150] The hole blocking layer is a layer that blocks holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby extending the life of the device and improving the performance of the device. The hole blocking layer of the present invention can be arranged on the light-emitting layer. As the hole blocking layer material of the organic electroluminescent device of the present invention, compounds with hole blocking effects known in the prior art can be used, such as the compounds disclosed in the following prior art: Appl. Phys. Lett. 75, 4 (1999), Appl. Phys. Lett. 83, 3858 (2003), JP2015111679A, KR1020180043220A, CN109564982A, KR1020180065246A.

[0151] The thickness of the hole blocking layer of the present invention may be 2-200 nm, preferably 5-150 nm, more preferably 5-50 nm, but the thickness is not limited to this range.

[0152] The electron transport layer may be disposed on the light emitting layer or (if present) the hole blocking layer. The electron transport layer material is a material that easily receives electrons from the cathode and transfers the received electrons to the light emitting layer. Preferably, the material has a high electron mobility. As the electron transport layer of the organic electroluminescent device of the present invention, the electron transport layer materials for organic electroluminescent devices disclosed in the prior art can be used, for example, the compounds disclosed in the following prior art: CN1784388A, CN1625552A, CN107431141A, CN107431141A, KR1020160149041A, KR1020160149041A, CN103827256A, KR101847347B1, KR1020190050658A, CN102574813A, CN107721979A, KR1020100073954A.

[0153] In a preferred embodiment of the present invention, the electron transport layer further comprises other compounds conventionally used in electron transport layers, for example, Alq3, LiQ, preferably LiQ.

[0154] The thickness of the electron transport layer of the present invention may be 10-80 nm, preferably 20-60 nm, and more preferably 25-45 nm, but the thickness is not limited to this range.

[0155] The electron injection layer may be disposed on the electron transport layer. The electron injection layer material is generally preferably a material with a low work function, so that electrons are easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present invention, the electron injection layer material for organic electroluminescent devices disclosed in the prior art can be used, for example: LiF, Cs 2 CO 3 、CsF、Csq、NaF、MgF 2 , CaF 2 、Al 2 O 3 , Yb, etc.

[0156] The thickness of the electron injection layer of the present invention may be 0.1-5 nm, preferably 0.5-3 nm, and more preferably 0.8-1.5 nm, but the thickness is not limited to this range.

[0157] The second electrode may be disposed above the electron transport region. The second electrode may be a cathode. The second electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the second electrode is a transmissive electrode, the second electrode may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF, Ba, Ag, or a compound or mixture thereof; when the second electrode is a semi-transmissive electrode or a reflective electrode, the second electrode may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or a compound or mixture thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0158] The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass can or a metal can; or a thin film covering the entire surface of the organic layer.

[0159] The method for preparing the organic electroluminescent device of the present invention comprises laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer and a cathode successively on a substrate, and optionally a covering layer. In this regard, vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing or LITI methods can be used, but are not limited thereto. In the present invention, it is preferred to use a vacuum evaporation method to form the various layers. Those skilled in the art can conventionally select various process conditions in the vacuum evaporation method according to actual needs.

[0160] Preparation of compounds

[0161] 1. Synthesis of intermediate P

[0162] Synthesis of intermediate P1:

[0163]

[0164] Add raw material T1 (25mmol, 7.3g), potassium carbonate (62.5mmol, 8.6g), tricyclohexylphosphine (1.25mmol, 0.35g), palladium acetate (0.4mmol, 90mg) into a two-necked flask, add 100mL of anhydrous DMF under nitrogen protection, stir at room temperature for 30 minutes, add raw material R1 (25mmol, 6.9g) under nitrogen protection, stir at 140°C for 12 hours under nitrogen protection, filter, wash with water, dry and pass through a column to obtain intermediate P1.

[0165] Synthesis of intermediate P2:

[0166]

[0167] Add raw material T1 (25mmol, 7.3g), potassium carbonate (62.5mmol, 8.6g), tricyclohexylphosphine (1.25mmol, 0.35g), palladium acetate (0.4mmol, 90mg) into a two-necked flask, add 100mL of anhydrous DMF under nitrogen protection, stir at room temperature for 30 minutes, add raw material R2 (25mmol, 6.7g) under nitrogen protection, stir at 140°C for 13 hours under nitrogen protection, filter, wash with water, dry and pass through a column to obtain intermediate P2.

[0168] Synthesis of intermediate P3:

[0169]

[0170] Add raw material T1 (25mmol, 7.3g), potassium carbonate (62.5mmol, 8.6g), tricyclohexylphosphine (1.25mmol, 0.35g), palladium acetate (0.4mmol, 90mg) into a two-necked flask, add 100mL of anhydrous DMF under nitrogen protection, stir at room temperature for 30 minutes, add raw material R3 (25mmol, 6.7g) under nitrogen protection, stir at 140°C for 12 hours under nitrogen protection, filter, wash with water, dry and pass through a column to obtain intermediate P3.

[0171] Synthesis of intermediate P4:

[0172]

[0173] A three-necked flask was filled with argon, and 10 mL of DMF, raw material T2 (6.1 mmol, 2.0 g), raw material R4 (14.6 mmol, 2.4 g), copper iodide (0.84 mmol, 0.16 g), 1,10-phenanthroline (1.33 mmol, 0.24 g) and cesium carbonate (14.6 mmol, 4.8 g) were added, and the mixture was degassed at -78 ° C and heated at 100 ° C for 2 hours. 100 mL of ethyl acetate and 100 mL of saturated NH 4 The organic layer was separated and the aqueous solution was extracted with 50 mL of ethyl acetate. The organic phases were combined and filtered through Na 2 SO 4 The organic phase was dried and evaporated under reduced pressure, and purified by silica gel column chromatography to obtain intermediate W1.

[0174]

[0175] In a three-necked flask, intermediate W1 (0.25 mmol, 0.1 g), raw material R5 (2.5 mmol, 0.5 g) and 3 mL H 2 SO 4(0.4 M methanol) solution, the mixture was heated under reflux for 12 hours. After the reaction was completed, the reaction mixture was diluted with dichloromethane and washed twice with water. The separated organic solution was passed through Na 2 SO 4 The organic phase was dried and concentrated under reduced pressure, and then purified by silica gel column chromatography, slurried with ethyl acetate, filtered to obtain a solid powder, and dried to obtain intermediate W2.

[0176]

[0177] In a dry three-necked flask, intermediate W2 (1 mmol, 0.7 g) was added, and 30 mL of TBAF (1.0 M, THF) solution was added dropwise. The reaction solution was stirred at room temperature for 13 hours. After the reaction was completed, the aqueous phase was extracted with 150 mL of ethyl acetate. The organic phase was concentrated and the residue was purified by silica gel column chromatography to obtain intermediate W3.

[0178] Into a three-necked flask, raw material T3 (15 mmol, 2.4 g), intermediate W3 (12 mmol, 5.5 g), CuI catalyst (1 mmol, 0.2 g), K 3 PO 4 (25mmol, 5.3g), followed by the addition of trans-1,2-cyclohexanediamine (1.8mmol, 0.2g) and 120mL of dioxane under nitrogen atmosphere, stirred at 110°C for 15 hours, the reaction mixture was cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compound was separated by silica gel column chromatography to obtain intermediate P4.

[0179] 2. Synthesis of Intermediate Q

[0180] Synthesis of intermediate Q1:

[0181]

[0182] Add raw material M1 (18.4 mmol, 6.2 g) and cesium carbonate (55.2 mmol, 18.0 g) into a two-necked flask, add 120 mL of anhydrous DMF under nitrogen protection, stir at room temperature for 30 minutes, add raw material M2 (20.2 mmol, 5.6 g) under nitrogen protection, reflux the solution under magnetic stirring for 24 hours, cool, filter, wash with water, dry, and pass through a column to obtain intermediate Y1.

[0183]

[0184] The intermediate Y1 (5.1mmol, 3.0g) was dissolved in 50mL of tetrahydrofuran (THF) solution, and 4.7mL of n-butyl lithium (2.5M, 11.7mmol) n-hexane solution was slowly added at -78°C under nitrogen gas; after stirring at -78°C for 2 hours, 15mL of tetrahydrofuran solution of raw material M3 (5.5mmol, 1.3g) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. 20mL of dilute hydrochloric acid (1.0M) solution, distilled water and ethyl acetate were added to the reaction mixture, the aqueous layer was separated, and extracted three times with ethyl acetate. The combined organic layer was dried over sodium sulfate and filtered. After the solvent was removed under reduced pressure, the crude product was dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether was slowly added. The reaction mixture was stirred overnight and then treated with sodium bicarbonate (NaHCO 3 ) aqueous solution is slowly quenched. Then the aqueous layer is separated, extracted with dichloromethane, dried over sodium sulfate, filtered, distilled under reduced pressure, and passed through a column to obtain intermediate Q1.

[0185] Synthesis of intermediate Q2:

[0186]

[0187] Raw material M4 (18.4 mmol, 4.5 g) and cesium carbonate (55.2 mmol, 18.0 g) were added to a two-necked flask, and 120 mL of anhydrous DMF was added under nitrogen protection. The mixture was stirred at room temperature for 30 minutes. Raw material M5 (20.2 mmol, 7.2 g) was added under nitrogen protection, and the solution was refluxed under magnetic stirring for 24 hours. The mixture was cooled, filtered, washed with water, dried, and passed through a column to obtain intermediate Y2.

[0188]

[0189] Under nitrogen protection, at 0°C, 10 mL of a hexane solution of n-butyl lithium (1.6 M) was added dropwise to a 30 mL anhydrous ether solution of intermediate Y2 (7.2 mmol, 4.2 g) while stirring; the mixture was stirred at 0°C for 1 hour, and then 10 mL of an anhydrous toluene solution containing raw material M6 (8.0 mmol, 2.4 g) was added dropwise; the reaction mixture was stirred at 35°C for 2 hours, and then cooled to room temperature; after adding water, the product was extracted with ethyl acetate. The combined organic layer was washed with brine and precipitated with anhydrous sodium sulfate (Na 2 SO 4 ) and dried; filtered, distilled under reduced pressure, and passed through a column to obtain intermediate Q2.

[0190] 3. Synthesis of Examples

[0191] Example 1 Synthesis of Compound 34:

[0192]

[0193] To a three-necked flask were added intermediate Q1 (5 mmol, 3.4 g), intermediate P1 (5 mmol, 2.2 g), CuI catalyst (1 mmol, 0.2 g), K 3 PO 4 (25mmol, 5.3g), followed by the addition of trans-1,2-cyclohexanediamine (1.8mmol, 0.2g) and 80mL of dioxane under a nitrogen atmosphere, stirred at 110°C for 15 hours, and then the reaction mixture was cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compound was separated by silica gel column chromatography to obtain intermediate J1.

[0194]

[0195] In a three-necked flask, under nitrogen protection, intermediate J1 (10mmol, 10.4g) and 120mL o-dichlorobenzene were added. 2.5M tert-butyl lithium in n-hexane solution (30mmol, 12mL) was added at -78°C, the system was heated to 60°C and reacted for 2 hours, then boron tribromide (15mmol, 1.5mL) was added at 0°C, the reaction was continued at room temperature for 5 hours, then N,N-diisopropylethylamine (20mmol, 3.5mL) was added to the system at 0°C, heated to 200°C and reacted for 12 hours. After the reaction, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain compound 34. In toluene solution (1×10 -5 The half-peak width is 28 nm. 1 H NMR(400MHz,Chloroform-d)δ8.95(d,1H),8.57(d,1H),8.31–8.20(m,2H),8.11(m,1H),7.94–7.76(m,2H),7.74 –7.54(m,4H),7.52–7.36(m,8H),7.32(m,1H),7.29–7.17(m,4H),7.10(d,1H),7.01(d,1H),1.54–1.07(m,45H).

[0196] Example 2 Synthesis of Compound 56:

[0197]

[0198] Into a three-necked flask, intermediate Q1 (5 mmol, 3.4 g), raw material A1 (5 mmol, 1.6 g), CuI catalyst (1 mmol, 0.2 g), K 3 PO 4(25mmol, 5.3g), followed by the addition of trans-1,2-cyclohexanediamine (1.8mmol, 0.2g) and 70mL of dioxane under nitrogen atmosphere, stirred at 110°C for 13 hours, the reaction mixture was cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compound was separated by silica gel column chromatography to obtain intermediate J2.

[0199]

[0200] In a three-necked flask, under nitrogen protection, intermediate J2 (10mmol, 9.2g) and 100mL o-dichlorobenzene were added. 2.5M tert-butyl lithium in n-hexane solution (30mmol, 12mL) was added at -78°C, the system was heated to 60°C and reacted for 2 hours, then boron tribromide (15mmol, 1.5mL) was added at 0°C, the reaction was continued at room temperature for 6 hours, then N,N-diisopropylethylamine (20mmol, 3.5mL) was added to the system at 0°C, heated to 200°C and reacted for 10 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain compound 56. In toluene solution (1×10 -5 The half-peak width is 26 nm.

[0201] Example 3 Synthesis of Compound 85:

[0202]

[0203] To a three-necked flask were added intermediate Q1 (5 mmol, 3.4 g), intermediate P2 (5 mmol, 2.2 g), CuI catalyst (1 mmol, 0.2 g), K 3 PO 4 (25mmol, 5.3g), followed by the addition of trans-1,2-cyclohexanediamine (1.8mmol, 0.2g) and 90mL of dioxane under nitrogen atmosphere, stirred at 110°C for 15 hours, the reaction mixture was cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compound was separated by silica gel column chromatography to obtain intermediate J3.

[0204]

[0205] In a three-necked flask, under nitrogen protection, intermediate J3 (10mmol, 10.3g) and 120mL o-dichlorobenzene were added. 2.5M tert-butyl lithium in n-hexane solution (30mmol, 12mL) was added at -78°C, the system was heated to 60°C and reacted for 2 hours, then boron tribromide (15mmol, 1.5mL) was added at 0°C, the reaction was continued at room temperature for 6 hours, then N,N-diisopropylethylamine (20mmol, 3.5mL) was added to the system at 0°C, heated to 200°C and reacted for 12 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain compound 85. In toluene solution (1×10 -5 The half-peak width is 26 nm. 1 H NMR(400MHz,Chloroform-d)δ8.98(d,1H),8.65(d,1H),8.34–8.21(m,2H),8.14(m, 1H),7.99–7.75(m,4H),7.73–7.19(m,18H),7.12(d,1H),7.04(d,1H),1.38(m,36H).

[0206] Example 4 Synthesis of Compound 98:

[0207]

[0208] Into a three-necked flask, intermediate Q2 (5 mmol, 3.3 g), raw material A1 (5 mmol, 1.6 g), CuI catalyst (1 mmol, 0.2 g), K 3 PO 4 (25mmol, 5.3g), followed by the addition of trans-1,2-cyclohexanediamine (1.8mmol, 0.2g) and 90mL of dioxane under nitrogen atmosphere, stirred at 110°C for 16 hours, and then the reaction mixture was cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compound was separated by silica gel column chromatography to obtain intermediate J4.

[0209]

[0210] In a three-necked flask, under nitrogen protection, intermediate J4 (10mmol, 9.4g) and 110mL o-dichlorobenzene were added. 2.5M tert-butyl lithium in n-hexane solution (30mmol, 12mL) was added at -78°C, the system was heated to 60°C and reacted for 2 hours, then boron tribromide (15mmol, 1.5mL) was added at 0°C, the reaction was continued at room temperature for 6 hours, then N,N-diisopropylethylamine (20mmol, 3.5mL) was added to the system at 0°C, heated to 200°C and reacted for 12 hours. After the reaction, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain compound 98. In toluene solution (1×10 -5 The half-peak width is 27 nm. 1 H NMR(400MHz,Chloroform-d)δ8.96(d,1H),8.67(d,1H),8.53–8.39(m,1H),8.13 –8.02(m,1H),7.98–7.78(m,5H),7.75–7.27(m,21H),7.14(d,1H),1.29(d,18H).

[0211] Example 5 Synthesis of Compound 108:

[0212]

[0213] Into a three-necked flask, intermediate Q1 (5 mmol, 3.4 g), raw material A2 (5 mmol, 1.6 g), CuI catalyst (1 mmol, 0.2 g), K 3 PO 4 (25mmol, 5.3g), followed by the addition of trans-1,2-cyclohexanediamine (1.8mmol, 0.2g) and 90mL of dioxane under a nitrogen atmosphere, stirred at 110°C for 12 hours, and then the reaction mixture was cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compound was separated by silica gel column chromatography to obtain intermediate J5.

[0214]

[0215] In a three-necked flask, under nitrogen protection, intermediate J5 (10mmol, 9.2g) and 100mL o-dichlorobenzene were added. 2.5M tert-butyl lithium in n-hexane solution (30mmol, 12mL) was added at -78°C, the system was heated to 60°C and reacted for 2 hours, then boron tribromide (15mmol, 1.5mL) was added at 0°C, the reaction was continued at room temperature for 6 hours, then N,N-diisopropylethylamine (20mmol, 3.5mL) was added to the system at 0°C, heated to 200°C and reacted for 14 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain compound 108. In toluene solution (1×10 -5 The half-peak width is 25 nm. 1 HNMR(400MHz,Chloroform-d)δ8.92(d,1H),8.33–8.23(m,2H),8.11(m,1H),7.98–7.72(m,4H),7.68–7.18(m,21H),7.06(m,2H),1.30(d,18H).

[0216] Example 6 Synthesis of Compound 137:

[0217]

[0218] To a three-necked flask were added intermediate Q1 (5 mmol, 3.2 g), intermediate P3 (5 mmol, 2.2 g), CuI catalyst (1 mmol, 0.2 g), K 3 PO 4 (25mmol, 5.3g), followed by the addition of trans-1,2-cyclohexanediamine (1.8mmol, 0.2g) and 90mL of dioxane under nitrogen atmosphere, stirred at 110°C for 14 hours, the reaction mixture was cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compound was separated by silica gel column chromatography to obtain intermediate J6.

[0219]

[0220] In a three-necked flask, under nitrogen protection, intermediate J6 (10mmol, 10.3g) and 120mL o-dichlorobenzene were added. 2.5M tert-butyl lithium in n-hexane solution (12mmol, 4.8mL) was added at -78°C, the system was heated to 60°C and reacted for 2 hours, then boron tribromide (15mmol, 1.5mL) was added at 0°C, the reaction was continued at room temperature for 6 hours, then N,N-diisopropylethylamine (20mmol, 3.5mL) was added to the system at 0°C, heated to 200°C and reacted for 15 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain compound 137. In toluene solution (1×10 -5 The half-peak width is 25 nm. 1 H NMR (400MHz, Chloroform-d) δ8.95(d,1H),8.35–8.19(m,2H),8.13(m,1H),7.95–7.74(m,4H),7.73–7.17(m,19H),7.04(m,2H),1.35(m,36H).

[0221] Example 7 Synthesis of Compound 161:

[0222]

[0223] To a three-necked flask were added intermediate Q1 (5 mmol, 3.2 g), intermediate P4 (5 mmol, 2.7 g), CuI catalyst (1 mmol, 0.2 g), K 3 PO 4 (25mmol, 5.3g), followed by the addition of trans-1,2-cyclohexanediamine (1.8mmol, 0.2g) and 90mL of dioxane under nitrogen atmosphere, stirred at 110°C for 13 hours, the reaction mixture was cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compound was separated by silica gel column chromatography to obtain intermediate J7.

[0224]

[0225] In a three-necked flask, under nitrogen protection, intermediate J7 (10mmol, 11.4g) and 120mL o-dichlorobenzene were added. 2.5M tert-butyl lithium in n-hexane solution (12mmol, 4.8mL) was added at -78°C, the system was heated to 60°C and reacted for 3 hours, then boron tribromide (15mmol, 1.5mL) was added at 0°C, the reaction was continued at room temperature for 6 hours, then N,N-diisopropylethylamine (20mmol, 3.5mL) was added to the system at 0°C, heated to 200°C and reacted for 15 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain compound 161. In toluene solution (1×10 -5 The half-peak width is 29 nm. 1 H NMR(400MHz,Chloroform-d)δ8.99(d,1H),8.37–8.21(m,2H),8.08(m,1H),7.91 –7.75(m,2H),7.72–7.21(m,33H),7.19–7.07(m,2H),6.98(d,1H),1.37(d,18H).

[0226] Note: The half-peak width (FWHM) is obtained by testing the Fluorolog-3 series fluorescence spectrometer of Horiba.

[0227] The structural characteristics of the compounds obtained in each example are shown in Table 1

[0228] Table 1

[0229]

[0230]

[0231] The following describes in detail the application effect of the OLED material synthesized by the present invention in the device through device embodiments 1-7 and device comparative examples 1-2. The device manufacturing process of device embodiments 2-7 and device comparative examples 1-2 of the present invention is exactly the same as that of device embodiment 1, and the same substrate material and electrode material are used. The film thickness of the electrode material is also the same. The difference is that the doping material of the light-emitting layer in the device is replaced. The layer structure and test results of each device embodiment are shown in Table 2-1 and Table 3 respectively.

[0232] Device Example 1

[0233] like Figure 1As shown, the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness is 150nm) is washed, that is, washing with a cleaning agent (SemicleanM-L20), washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, a vacuum evaporation device is used to evaporate HT-1 and HI-1 with a film thickness of 10nm as a hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then evaporate HT-1 with a thickness of 60nm as a hole transport layer 4. Then evaporate EB-1 with a thickness of 30nm as an electron blocking layer 5. After the above electron blocking material is evaporated, the light-emitting layer 6 of the OLED light-emitting device is prepared, using GH-1 and GH-2 as the main materials, compound 34 as the doping material, GH-1, GH-2 and compound 34 The mass ratio is 69:30:1, and the film thickness of the light-emitting layer is 30nm. After the above-mentioned light-emitting layer 6, HB-1 was vacuum-deposited to a thickness of 5 nm, which was the hole blocking layer 7. After the above-mentioned hole blocking layer 7, ET-1 and Liq were vacuum-deposited to a thickness of 30 nm, with a mass ratio of ET-1 to Liq of 1:1. On the electron transport layer 8, a LiF layer with a thickness of 1 nm was made by vacuum evaporation, which was the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 80 nm was made by vacuum evaporation, with a mass ratio of Mg to Ag of 1:9, which was used as the cathode layer 10.

[0234] The following describes in detail the application effect of the OLED material synthesized by the present invention in the device through device embodiments 8-14 and device comparative examples 3-4. The device manufacturing process of device embodiments 9-14 and device comparative examples 3-4 of the present invention is exactly the same as that of device embodiment 8, and the same substrate material and electrode material are used. The film thickness of the electrode material is also the same. The difference is that the doping material of the light-emitting layer in the device is replaced. The layer structure and test results of each device embodiment are shown in Table 2-2 and Table 3, respectively.

[0235] Device Example 8

[0236] The transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness is 150nm) is washed, that is, washed with a cleaning agent (SemicleanM-L20), washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, a vacuum evaporation device is used to evaporate HT-1 and HI-1 with a film thickness of 10nm as the hole injection layer 3, and the mass ratio of HT-1 to HI-1 is 97:3. Then, HT-1 with a thickness of 60nm is evaporated as the hole transport layer 4. Then, EB-1 with a thickness of 30nm is evaporated as the electron blocking layer 5. After the above-mentioned electron blocking material is deposited, the light-emitting layer 6 of the OLED light-emitting device is prepared, using GH-1 and GH-2 as the main materials, GD-1 as the first doping material, and compound 34 as the second doping material. The mass ratio of GH-1, GH-2, GD-1 and compound 34 is 66.5:30:3:0.5, and the thickness of the light-emitting layer is 30nm. After the above-mentioned light-emitting layer 6, HB-1 is vacuum-deposited with a film thickness of 5nm. This layer is the hole blocking layer 7. After the above-mentioned hole blocking layer 7, ET-1 and Liq are vacuum-deposited. The mass ratio of ET-1 and Liq is 1:1, and the film thickness is 30nm. This layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1nm is prepared by a vacuum evaporation device. This layer is the electron injection layer 9. On the electron injection layer 9 , a Mg:Ag electrode layer with a film thickness of 80 nm was produced by a vacuum evaporation device. The mass ratio of Mg to Ag was 1:9. This layer was used as the cathode layer 10 .

[0237] The molecular structure formula of the relevant materials is shown below:

[0238]

[0239] After the OLED light-emitting device is completed as described above, the anode and cathode are connected by a known driving circuit, and the current efficiency and life of the device are measured. The device examples and comparative examples prepared by the same method are shown in Table 2-1 and Table 2-2; the test results of the current efficiency and life of the obtained device are shown in Table 3.

[0240] Table 2-1

[0241]

[0242]

[0243] Table 2-2

[0244]

[0245]

[0246] Table 3

[0247]

[0248] Note: Current efficiency and luminescence peak are tested using IVL (current-voltage-luminance) test system (Suzhou Fushida Scientific Instrument Co., Ltd.); life test system is EAS-62C OLED device life tester from Japan System Technology Co., Ltd.; LT95 refers to the time it takes for the device brightness to decay to 95%; all data are at 10mA / cm 2 Next test.

[0249] It can be seen from the device data results in Table 3 that the luminescence peak of the compound of the present invention is between 510 and 540 nm, which can well achieve the effect of green luminescence; compared with device comparison examples 1-4, the organic light-emitting device of the present invention, whether in a single-doping system or a double-doping system, has a greatly improved current efficiency and lifespan relative to OLED devices of known materials; when an exciton-sensitizing material is used as the first doping, the device efficiency is significantly improved compared to a single-doping system.

[0250] In summary, the above are only preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention should be included in the protection scope of the present invention.

Claims

1. A boron-containing resonance type organic compound, characterized in that: The structure of the boron-containing resonance-type organic compound is shown in general formula (1): In the general formula (1), R1 and R2, which are the same or different each time, represent a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a C1-C2 group substituted or unsubstituted by a substituent group, 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C5~C 10 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 An aryl group, a 5-30 membered heteroaryl group which may be substituted by a substituent or not, or a borane group which may be substituted by a substituent or not; R1 and R2 can be connected to form a C6-C 30 Aromatic ring, 5-30 membered heteroaromatic ring substituted or unsubstituted by substituents, C5-C 30 aliphatic ring; Each occurrence of Z1, Z2, Z3, Z4, Z5, and Z6 is independently represented by N, CH, or CR a ; R a Deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C5~C 10 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of an aryl group, a 5-30-membered heteroaryl group which may be substituted by a substituent, and a borane group which may be substituted by a substituent; Ar1 and Ar2, which are the same or different each time, represent hydrogen atoms, deuterium atoms, halogen atoms, C1-C2 atoms substituted or unsubstituted by substituents. 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C5~C 10 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 An aryl group, a 5-30 membered heteroaryl group which may be substituted by a substituent or not, or a borane group which may be substituted by a substituent or not; Each occurrence of M1, M2, M3, and M4 that is the same or different indicates that C6 to C6 is substituted or unsubstituted by one or more R. 30 An aromatic ring, a 5-30 membered heteroaromatic ring substituted or unsubstituted by one or more R; R, which is the same or different each time, represents a deuterium atom, a tritium atom, a halogen atom, a cyano group, a C1-C2 group substituted or unsubstituted by a substituent 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C5~C 10 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of an aryl group, a 5-30-membered heteroaryl group which may be substituted by a substituent, and a borane group which may be substituted by a substituent; The substitution mode of R is a single bond or a ring connection; Each occurrence of X, whether the same or different, represents a carbon atom or a silicon atom; The substituents are selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Any one or more of aryl, 5-30 membered heteroaryl, deuterium or tritium substituted 5-30 membered heteroaryl; The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

2. The boron-containing resonance type organic compound according to claim 1, characterized in that: The structure of the boron-containing resonance-type organic compound is shown in general formula (A): In the general formula (A), R1 to R 12 Each occurrence independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a C1-C2 group substituted or unsubstituted by a substituent 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C5~C 10 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 An aryl group, a 5-30 membered heteroaryl group which may be substituted by a substituent or not, or a borane group which may be substituted by a substituent or not; R1~R 12 Any two adjacent groups can be connected to form a C6~C 30 Aromatic ring, 5-30 membered heteroaromatic ring substituted or unsubstituted by substituents, C5-C 30 aliphatic ring; Each occurrence of Z1, Z2, Z3, Z4, Z5, and Z6 is independently represented by N, CH, or CR a ; R a Deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C5~C 10 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of an aryl group, a 5-30-membered heteroaryl group which may be substituted by a substituent, and a borane group which may be substituted by a substituent; Ar1 and Ar2, which are the same or different each time, represent hydrogen atoms, deuterium atoms, halogen atoms, C1-C2 atoms substituted or unsubstituted by substituents. 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C5~C 10 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 An aryl group, a 5-30 membered heteroaryl group which may be substituted by a substituent or not, or a borane group which may be substituted by a substituent or not; Each occurrence of M1 that is the same or different indicates that C6~C 30 An aromatic ring, a 5-30 membered heteroaromatic ring substituted or unsubstituted by one or more R; R, which is the same or different each time, represents a deuterium atom, a tritium atom, a halogen atom, a cyano group, a C1-C2 group substituted or unsubstituted by a substituent 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C5~C 10 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of an aryl group, a 5-30-membered heteroaryl group which may be substituted by a substituent, and a borane group which may be substituted by a substituent; The substitution mode of R is a single bond or a ring connection; Each occurrence of X, whether the same or different, represents a carbon atom or a silicon atom; The substituents are selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Any one or more of aryl, 5-30 membered heteroaryl, deuterium or tritium substituted 5-30 membered heteroaryl; The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

3. The boron-containing resonance type organic compound according to claim 2, characterized in that: The structure of the boron-containing resonance-type organic compound is shown in any one of the general formulas (A-1) to (A-4): In the general formulas (A-1) to (A-4), R1 to R 12 , Ar1, Ar2, X, Z1, Z2, Z3, Z4, Z5, and Z6 are the same as those in the general formula (A); Z, Z7, Z8, Z9, Z 10 , Z 11 Each occurrence is independently represented by N, CH or CR a ; R a Deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C5~C 10 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of an aryl group, a 5-30-membered heteroaryl group which may be substituted by a substituent, and a borane group which may be substituted by a substituent; Y represents O, S, NR 13 or C(R 14 )(R 15 ); R 13 Indicates C6~C 30 Aryl, or one of 5-30 heteroaryl groups which may be substituted by a substituent or unsubstituted; R 14 , R 15 Indicates C1 to C2 substituted or unsubstituted by a substituent 10 Alkyl, substituted or unsubstituted C6~C 30 Aryl, 5-30 membered heteroaryl which may be substituted by a substituent; Ar3 and Ar4, when they appear, are independently hydrogen atoms, deuterium atoms, halogen atoms, C1-C2 atoms substituted or unsubstituted with substituents. 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C5~C 10 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 An aryl group, a 5-30 membered heteroaryl group which may be substituted by a substituent or not, or a borane group which may be substituted by a substituent or not; The substituents are selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Any one or more of aryl, 5-30 membered heteroaryl, deuterium or tritium substituted 5-30 membered heteroaryl; The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

4. The boron-containing resonance type organic compound according to claim 2, characterized in that: The structure of the boron-containing resonance-type organic compound is shown in any one of the general formulas (A-5) to (A-8): In the general formulas (A-5) to (A-8), R1 to R 12 , Ar1, Ar2, Z1, Z2, Z3, Z4, Z5, and Z6 are the same as those in the general formula (A); Z, Z7, Z8, Z9, Z 10 , Z 11 Each occurrence is independently represented by N, CH or CR a ; R a Deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C5~C 10 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of an aryl group, a 5-30-membered heteroaryl group which may be substituted by a substituent, and a borane group which may be substituted by a substituent; R 13 Indicates C6~C 30 Aryl, or one of 5-30 heteroaryl groups which may be substituted by a substituent or unsubstituted; Ar3 and Ar4, when they appear, are independently hydrogen atoms, deuterium atoms, halogen atoms, C1-C2 atoms substituted or unsubstituted with substituents. 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C5~C 10 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 An aryl group, a 5-30 membered heteroaryl group which may be substituted by a substituent or not, or a borane group which may be substituted by a substituent or not; The substituents are selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Any one or more of aryl, 5-30 membered heteroaryl, deuterium or tritium substituted 5-30 membered heteroaryl; The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

5. The boron-containing resonance type organic compound according to claim 2, characterized in that: The structure of the boron-containing resonance-type organic compound is shown in any one of the general formulas (A-9) to (A-12): In the general formulas (A-9) to (A-12), R3 to R 12 , Ar1, Ar2, Z1, Z2, Z3, Z4, Z5, and Z6 are the same as those in the general formula (A); Z, Z7, Z8, Z9, Z 10 , Z 11 Each occurrence is independently represented by N, CH or CR a ; R a Deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C5~C 10 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 One of an aryl group, a 5-30-membered heteroaryl group which may be substituted by a substituent, and a borane group which may be substituted by a substituent; R 13 Indicates C6~C 30 Aryl, or one of 5-30 heteroaryl groups which may be substituted by a substituent or unsubstituted; Ar3 and Ar4, when they appear, are independently hydrogen atoms, deuterium atoms, halogen atoms, C1-C2 atoms substituted or unsubstituted with substituents. 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C5~C 10 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 An aryl group, a 5-30 membered heteroaryl group which may be substituted by a substituent or not, or a borane group which may be substituted by a substituent or not; The substituents are selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Any one or more of aryl, 5-30 membered heteroaryl, deuterium or tritium substituted 5-30 membered heteroaryl; The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

6. The boron-containing resonance type organic compound according to claim 2, characterized in that: The structure of the boron-containing resonance-type organic compound is shown in any one of the general formulas (A-13) to (A-16): In the general formulas (A-13) to (A-16), R a , R8, R 11 , Ar1, Ar2, X, Z1, Z2, Z3, Z4, Z5, and Z6 are the same as those in the general formula (A); R 13 Indicates C6~C 30 Aryl, or one of 5-30 heteroaryl groups which may be substituted by a substituent or unsubstituted; Ar3 and Ar4, when they appear, are independently hydrogen atoms, deuterium atoms, halogen atoms, C1-C2 atoms substituted or unsubstituted with substituents. 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C5~C 10 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 An aryl group, a 5-30 membered heteroaryl group which may be substituted by a substituent or not, or a borane group which may be substituted by a substituent or not; The substituents are selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Any one or more of aryl, 5-30 membered heteroaryl, deuterium or tritium substituted 5-30 membered heteroaryl; The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

7. The boron-containing resonance-type organic compound according to any one of claims 1 to 6, characterized in that: The M1, M2, M3, and M4 are represented by the following groups substituted or unsubstituted by R: any one of phenyl, naphthyl, anthracenyl, phenanthrenyl, pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, indole [3,2,1-jk] carbazolyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and spirofluorenyl; The R, R a represented by a deuterium atom, a halogen atom, a cyano group, a methyl group which may be substituted by a substituent, an ethyl group which may be substituted by a substituent, an isopropyl group which may be substituted by a substituent, a tert-butyl group which may be substituted by a substituent, a cyclohexyl group which may be substituted by a substituent, an adamantyl group which may be substituted by a substituent, a phenyl group which may be substituted by a substituent, a biphenyl group which may be substituted by a substituent, a terphenyl group which may be substituted by a substituent, a naphthyl group which may be substituted by a substituent, an anthracenyl group which may be substituted by a substituent, a phenanthryl group which may be substituted by a substituent, a pyridyl group which may be substituted by a substituent, and a quinolyl group which may be substituted by a substituent , a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted amino group, and a substituted or unsubstituted triazinyl group; R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 Each of the above is independently a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a methyl group which may be substituted or unsubstituted, an ethyl group which may be substituted or unsubstituted, an isopropyl group which may be substituted or unsubstituted, a tert-butyl group which may be substituted or unsubstituted, a cyclohexyl group which may be substituted or unsubstituted, an adamantyl group which may be substituted or unsubstituted, a phenyl group which may be substituted or unsubstituted, a biphenyl group which may be substituted or unsubstituted, a terphenyl group which may be substituted or unsubstituted, a naphthyl group which may be substituted or unsubstituted, an anthracenyl group which may be substituted or unsubstituted, a phenanthrenyl group which may be substituted or unsubstituted, a pyridyl group which may be substituted or unsubstituted, unsubstituted quinolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazinyl; Ar1, Ar2, Ar3, and Ar4 are independently substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted thiazolyl ... substituted quinolyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazinyl; The R 13 substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzofuranyl ... substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted N-phenylcarbazolyl group, substituted or unsubstituted 9,9-dimethylfluorenyl group, substituted or unsubstituted 9,9-diphenylfluorenyl group, substituted or unsubstituted spirofluorenyl group, substituted or unsubstituted amino group, substituted or unsubstituted triazinyl group; The R 14 , R 15 represented by a methyl group substituted or unsubstituted by a substituent, an ethyl group substituted or unsubstituted by a substituent, an isopropyl group substituted or unsubstituted by a substituent, a tert-butyl group substituted or unsubstituted by a substituent, a cyclohexyl group substituted or unsubstituted by a substituent, an adamantyl group substituted or unsubstituted by a substituent, a phenyl group substituted or unsubstituted by a substituent, a biphenyl group substituted or unsubstituted by a substituent, a terphenyl group substituted or unsubstituted by a substituent, a naphthyl group substituted or unsubstituted by a substituent, an anthracenyl group substituted or unsubstituted by a substituent, a phenanthrenyl group substituted or unsubstituted by a substituent, a pyridyl group substituted or unsubstituted by a substituent, a quinolyl group substituted or unsubstituted by a substituent, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazinyl; The substituents may be selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furanyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthryl group.

8. The boron-containing resonance-type organic compound according to any one of claims 1 to 6, characterized in that: The M1, M2, and M3 are represented by any of the following ring structures: The M4 is represented by any of the following ring structures: Y represents O, S, NR 13 or C(R 14 )(R 15 ); R 13 It is represented by phenyl; R 14 , R 15 It is represented by methyl or phenyl; Each occurrence of Z is independently represented by N, CH or CR a ; R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 They are independently represented as follows: Hydrogen atom, deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano, trifluoromethyl, Any of; The R, R a They are independently represented as follows: Deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano, trifluoromethyl, Any of; The Ar1, Ar2, Ar3, and Ar4 are represented by the following structures: Methyl, isopropyl, tert-butyl, Any one of.

9. The boron-containing resonance type organic compound according to claim 1, characterized in that: The specific structural formula of the boron-containing resonance-type organic compound is any one of the following structures:

10. An organic light-emitting device, comprising a substrate, a first electrode, a second electrode and a functional layer in sequence, wherein the functional layer is located between the first electrode and the second electrode, characterized in that: The functional layer comprises the boron-containing resonance-type organic compound according to any one of claims 1 to 9. Preferably, the functional layer comprises a light-emitting layer, the light-emitting layer comprises a main material and a doping material, and the doping material is the boron-containing resonance-type organic compound according to any one of claims 1-9. Preferably, the functional layer comprises a light-emitting layer, and the light-emitting layer comprises a first main material, a second main material and a doping material, at least one of the first main material and the second main material is a TADF material, and the doping material is the boron-containing resonance-type organic compound according to any one of claims 1-9.

11. The organic light-emitting device according to claim 10, wherein the functional layer comprises a light-emitting layer, the light-emitting layer comprises a host material, an exciton-sensitizing material and a doping material, the exciton-sensitizing material is a complex containing a metal element, and the doping material is a boron-containing resonance-type organic compound according to any one of claims 1 to 9.

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