A deuterated boron-nitrogen organic compound and an organic electroluminescent device prepared therefrom

Abstract

The application discloses a kind of deuterated boron-nitrogen organic compounds and the preparation of organic electroluminescent device, belong to semiconductor technical field.The structure of the organic compound of the present application is as shown in general formula (1), the compound of the present application is used as the green light doping material of the light-emitting layer of organic electroluminescent device, so as to improve the efficiency and life of device.

Description

Technical Field

[0001] This invention relates to the field of semiconductor technology, and more particularly to deuterated boron nitrogen organic compounds as OLED doping materials and organic electroluminescent devices containing the same. Background Technology

[0002] Traditional fluorescent doped materials, limited by early technologies, can only emit light using 25% of singlet excitons generated by electrical excitation. This results in low internal quantum efficiency (maximum 25%) and external quantum efficiency generally below 5%, significantly lower than that of phosphorescent devices. Phosphorescent materials, due to the strong spin-orbit coupling at their heavy atom centers, enhance intersystem crossing and can effectively utilize both singlet and triplet excitons generated by electrical excitation, achieving an internal quantum efficiency of 100%. However, most phosphorescent materials are expensive, have poor material stability, low color purity, and suffer from severe efficiency roll-off, limiting their application in OLEDs.

[0003] With the advent of the 5G era, higher requirements have been placed on color rendering standards. In addition to high efficiency and stability, luminescent materials also need narrower half-widths (HWHMs) to improve the purity of the emitted color in devices. Fluorescent dopants can achieve high fluorescence quantum density and narrow HWHM through molecular engineering. Significant breakthroughs have been achieved in blue fluorescent dopants, with the HWHM of boron-based materials reduced to below 30 nm. However, research on the green light region, which is more sensitive to the human eye, has mainly focused on phosphorescent dopants. However, the peak shape of these dopants is difficult to narrow using simple methods. Therefore, researching efficient green fluorescent dopants with narrow HWHMs is of great significance in meeting higher color rendering standards.

[0004] In addition, sensitization technology combines triplet exciton sensitizing materials with fluorescent doping materials. By using triplet exciton sensitizing materials as exciton sensitization media, it makes full use of triplet excitons and transfers energy to fluorescent doping materials through energy transfer, achieving 100% in-device quantum efficiency. This technology can make up for the shortcomings of insufficient exciton utilization in fluorescent doping materials and effectively leverage the high fluorescence quantum yield, high device stability, high color purity, and low cost of fluorescent doping materials, showing broad prospects in OLED applications.

[0005] Boron compounds with resonant structures are more likely to achieve narrow half-width emission (HWHM). When applied to sensitization techniques, these materials can enable the fabrication of devices with high efficiency and narrow HWHM emission. For example, CN 107507921 A and CN 110492006 A disclose a light-emitting layer combination technique using TADF materials with a minimum singlet and triplet energy level difference of less than or equal to 0.2 eV as the main body and boron-containing materials as dopants; CN 110492005 A and CN 110492009 A disclose a light-emitting layer combination scheme using excitocomplexes as the main body and boron-containing materials as dopants; both achieve efficiencies comparable to phosphorescence and relatively narrow HWHM. Developing sensitization techniques based on narrow HWHM boron-based light-emitting materials has unique advantages and strong potential for achieving BT.2020 display performance. Summary of the Invention

[0006] To address the aforementioned problems in the existing technology, this application provides a deuterated boron nitrogen organic compound and an organic electroluminescent device prepared therefrom. The compound of this invention can be used as a green light doping material for the light-emitting layer of an organic electroluminescent device, thereby significantly improving the device's lifetime.

[0007] The technical solution of the present invention is as follows: a deuterated boron nitrogen organic compound, the structure of which is shown in general formula (1):

[0008]

[0009] R1-R 20 Each instance of the same or different element is represented by a hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0010] R1-R 20 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom;

[0011] R1-R 20 Any two adjacent groups can also bond together to form a ring;

[0012] x represents one of O, S, N(Ra), C(Rb)(Rc), Si(Rd)(Re);

[0013] Raa, Rb, Rc, Rd, and Re independently represent substituted or unsubstituted C1 to C2 groups. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0014] Ra can also be combined with R 11 or / and R 12 Further bonding to form a ring; Rb and Rc, Rd and Re can also be directly connected to form a ring, or they can be bridged to form a ring;

[0015] R 12 It can also be connected to Ra by using O or S atoms as bridges;

[0016] The substituents used for the substituent groups are selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, and C1-C2 groups. 10 Alkyl groups, C3-C 10 cycloalkyl, C6-C 30 Aryl, C2~C 30 One or more of the heteroaryl groups;

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

[0018] Preferably, R1 and R 12 Between, between R2 and R3, between R3 and R4, between R5 and R6, between R6 and R7, between R8 and R9, between R9 and R 10 Between, R 10 and R 11 Between, R 13 and R 14 Between, R 14 and R 15 Between, R 15 and R 16 Between, R 16 and R 17 Between, R 17 and R 18 Between, R 18 and R 19 Between, R 19 and R 20 They are not connected or are connected by single bonds, double bonds, -O-, -S-, -N(R) f )-、-C(R g R h )-、-Si(R i R j - or -C(R) m )=C(Rn )-connect;

[0019] Ra and R 11 They are not connected or are connected by single bonds, double bonds, -O-, -S-, -N(R) f )-、-C(R g R h )-、-Si(R i R j - or -C(R) m )=C(R n )-connect;

[0020] Ra and R 12 They are not connected or are connected by single bonds, double bonds, -O-, -S-, -N(R) f )-、-C(R g R h )-、-Si(R i R j - or -C(R) m )=C(R n )-connect;

[0021] Rb and Rc are not connected or are connected via a single bond, double bond, -O-, -S-, or -N(R). f )-、-C(R g R h )-、-Si(R i R j - or -C(R) m )=C(R n )-connect;

[0022] Rd and Re are not connected or are connected via a single key, double key, -O-, -S-, or -N(R). f )-、-C(R g R h )-、-Si(R i R j - or -C(R) m )=C(R n )-connect;

[0023] The R f R g R h R i R j R m R n Each can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0024] The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C5~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups.

[0025] Preferably, the structure of the deuterated boron nitrogen organic compound is shown in general formula (2-1) to general formula (2-12):

[0026]

[0027]

[0028] R1-R 31 Each instance of the same or different element is represented by a hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1C 10 Alkoxy, substituted or unsubstituted C1-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0029] In general formulas (2-1), (2-2), (2-3), (2-6), and (2-7), R1-R 20 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom;

[0030] In general formulas (2-4) and (2-5), R1-R 23 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom;

[0031] In general formula (2-8), R1-R 21 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom;

[0032] In general formula (2-9), R1-R31 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom;

[0033] In general formulas (2-10) and (2-11), R1-R 22 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom;

[0034] In general formula (2-12), R1-R 29 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom;

[0035] X is represented by one of O, S, N (Ra), C (Rb)(Rc), Si (Rd)(Re);

[0036] Y represents one of O, S, N(Ra), C(Rb)(Rc), Si(Rd)(Re);

[0037] Ra, Rb, Rc, Rd, and Re independently represent substituted or unsubstituted C1 to C2 groups. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0038] Rb and Rc, Rd and Re can be directly connected to form a ring, or they can be connected to form a ring through a bridge;

[0039] The substituents used for the substituent groups are selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, and C1-C2 groups. 10 Alkyl groups, C3-C 10 cycloalkyl, C6-C 30 Aryl, C2~C 30 One or more of the heteroaryl groups;

[0040] The heteroatom in the heteroaryl group is selected from one of O, S, N, Si, and B.

[0041] The preferred R 13 -R 20 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom;

[0042] Or R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 21 R 22 R 23 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom;

[0043] Or R2, R3, R4, R5, R6, R7, R8, R9, R 10 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom;

[0044] Or R3, R6, R9, R 10 R 21 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom;

[0045] Or R3, R6, R9, R 21 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom;

[0046] Or at least one of R3 and R6 is represented as a deuterium atom or a group substituted by a deuterium atom;

[0047] Or R 13 -R 20 The 1, 2, 3, 4, 5, 6, 7, or 8 in the text represent deuterium atoms or groups substituted by deuterium atoms;

[0048] Or R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 21 R 22 R 23 The 1, 2, 3, 4, 5, 6, 7, or 8 in the text represent deuterium atoms or groups substituted by deuterium atoms;

[0049] Or R2, R3, R4, R5, R6, R7, R8, R9, R 10 The 1, 2, 3, 4, 5, 6, 7, or 8 in the text represent deuterium atoms or groups substituted by deuterium atoms;

[0050] Or R3, R6, R9, R 10 R 21 The 1, 2, 3, 4, or 5 in the text represent deuterium atoms or groups substituted by deuterium atoms;

[0051] Or R3, R6, R9, R 21 The 1, 2, 3, or 4 in the text represent deuterium atoms or groups substituted by deuterium atoms;

[0052] Alternatively, one or two of R3 and R6 may represent deuterium atoms or groups substituted by deuterium atoms.

[0053] Preferably, the structure of the deuterated boron nitrogen organic compound is shown in general formulas (3-1) to (3-7):

[0054]

[0055]

[0056] The tert-butyl group in formulas (3-1) to (3-7) can be replaced by deuterium;

[0057] R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 R 15 R 16 R 17 R 18 R 20 R 21 R 22 R 23 R 24 Each instance of the same or different element is represented by a hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C1 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups, R1-R 13 R 15 -R 18 R 20 -R 24 It can be directly bonded to the ring or connected via s, O bridges to form a parallel ring;

[0058] In general formulas (3-1), (3-2), (3-3), (3-6), and (3-7), R1, R2, R3, R4, R5, R6, R7, R8, R9, and R... 10 R 11 R 12 R 13 R 15 R 16 R 17 R 18 and R 20 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom;

[0059] In general formulas (3-4) and (3-5), R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R13 R 15 R 16 R 17 R 18 R 20 R 21 R 22 R 23 and R 24 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom;

[0060] In general formula (3-5), R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 12 R 13 R 15 R 16 R 17 R 18 R 20 R 21 R 22 R 23 and R 24 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom;

[0061] Preferred values ​​are R2, R4, R5, R7, and R. 13 R 15 -R 18 R 20 At least four of them are represented as deuterium atoms;

[0062] Ra, Rb, Rc, Rd, and Re are preferably any one of the following: substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted aromatic amino, substituted or substituted naphthyl, substituted or unsubstituted benzoyl, substituted or unsubstituted carbazole, substituted or unsubstituted benzocarbazole, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophenyl, and substituted or unsubstituted dibenzothiophenyl.

[0063] Ra can be associated with R 12 The benzene ring is linked together by substituted or unsubstituted fluorene groups;

[0064] Rb and Rc, Rd and Re can be linked together by direct bonding or by O and S bridges to form a loop;

[0065] R 12 It can also be connected to Ra by using O or S atoms as bridges;

[0066] The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, C1 to C2 atoms. 10 Alkyl groups, C3-C10 cycloalkyl, C6-C 30 Aryl, C2~C 30 One or more of the heteroaryl groups;

[0067] The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

[0068] Preferably, R1-R 31 Each of these can be independently represented as a hydrogen atom, deuterium atom, tritium atom, fluorine atom, cyano, adamantyl, methyl, deuterated methyl, tritated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritated ethyl, isopropyl, deuterated isopropyl, tritated isopropyl, tert-butyl, deuterated tert-butyl, tritated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterium Phenyl, tritylphenyl, diphenyl, deuterated diphenyl, trityl diphenyl, triphenyl, deuterated terphenyl, trityl terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, N-phenylcarbazole, 9 9-Dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazineyl, phenyl-substituted boronyl, methoxy, tert-butoxy;

[0069] Ra, R b R c R d R eEach of these can be independently represented as methyl, deuterated methyl, tritated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritated ethyl, isopropyl, deuterated isopropyl, tritated isopropyl, tert-butyl, deuterated tert-butyl, tritated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, tritated phenyl, diphenyl, deuterated diphenyl Phenyl, tritriphenyl, triphenyl, deuterated triphenyl, tritriphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, N-phenylcarbazole, 9,9-dimethylfluorenyl, spirofluorenyl One of the following: methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazineyl, phenyl-substituted boronyl, methoxy, and tert-butoxy.

[0070] The substituents used for the substituent groups are selected from one of the following: deuterium, tritium, fluorine, cyano, adamantyl, methyl, trimethyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, fluorine-substituted phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, diphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, phenyl-substituted amino, tert-butylphenyl-substituted amino, and phenyl-substituted triazine.

[0071] Preferably, R1-R 31 Each can be represented independently as shown in the following structure:

[0072] Hydrogen atom, deuterium atom, Any one of them;

[0073] Ra is represented by the following structure:

[0074] Any one of them.

[0075] Preferably, R1-R 31 Each can be represented independently as shown in the following structure:

[0076] Hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, ethyl group, isopropyl group, tert-butyl group Any one of them;

[0077] Ra is represented by the following structure:

[0078] Any one of them.

[0079] Preferably, the structure of the deuterated boron nitrogen organic compound is shown in general formula (3-1) to general formula (3-7);

[0080] The tert-butyl group in formulas (3-1) to (3-7) can be replaced by deuterium;

[0081] R1-R 13 R 15 -R 18 R 20 -R 24 Each instance of the same or different element is represented by a hydrogen atom, deuterium atom, tritium atom, halogen atom, or substituted or unsubstituted C1-C1 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups, R1-R 13 R 15 -R 18 R 20 -R 24 It can be directly bonded to the ring or connected via s, O bridges to form a parallel ring;

[0082] R1-R 13 R 15 -R 18 R 20 -R 24 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom;

[0083] Preferred values ​​are R2, R4, R5, R7, and R. 13 R 15 -R 18 R 20At least four of them are represented as deuterium atoms;

[0084] Ra, Rb, Rc, Rd, and Re are preferably any one of the following: substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted aromatic amino, substituted or substituted naphthyl, substituted or unsubstituted benzoyl, substituted or unsubstituted carbazole, substituted or unsubstituted benzocarbazole, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophenyl, and substituted or unsubstituted dibenzothiophenyl.

[0085] Ra can be associated with R 12 The benzene ring is linked together by substituted or unsubstituted butyl bridges;

[0086] Rb and Rc, Rd and Re can be linked together by direct bonding or by O and S bridges to form a loop;

[0087] R 12 It can be represented as O and S atoms, directly connected to the adjacent ring;

[0088] The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, C1 to C2 atoms. 10 Alkyl groups, C3-C 10 cycloalkyl, C6-C 30 Aryl, C2~C 30 One or more of the heteroaryl groups;

[0089] The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

[0090] Preferably, the structure of the deuterated boron nitrogen organic compound is shown in general formula (3-1) to general formula (3-7);

[0091] The tert-butyl group in formulas (3-1) to (3-7) can be replaced by deuterium;

[0092] R1-R 13 R 15 -R 1g R 20 -R 24 It can be represented as: substituted or unsubstituted phenyl, substituted or unsubstituted aromatic amino, substituted or unsubstituted phenylyl, substituted or unsubstituted carbazole, tert-butyl, methoxy, adamantyl, substituted or unsubstituted cycloalkyl, deuterium, carbazole, benzofuranyl, benzothiophene, cyano, silyl; R1-R 13 R 15 -R 1g R 20 -R 24 It can be directly bonded to the benzene ring or connected to form a fused ring through S and O atoms;

[0093] R2, R4, R5, R7, R 13 R 15 -R 18 R 20 At least four of them are represented as deuterium atoms;

[0094] Ra to Re can be represented as: substituted or unsubstituted phenyl, substituted or unsubstituted aromatic amino, substituted or unsubstituted phenylyl, substituted or unsubstituted carbazole, tert-butyl, adamantyl, carbazole, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophene, cyano, preferably with the following structures:

[0095]

[0096] Ra can be associated with R 12 The benzene ring is linked together by substituted or unsubstituted butyl bridges;

[0097] Rb and Rc, Rd and Re can be linked into a ring through direct bonding or through O and S bridges;

[0098] R 12 This can be represented as O, s atoms connected to adjacent rings;

[0099] The groups used to replace the above substituents may be selected from one or more of the following atoms or segments: hydrogen atom, deuterium atom, methoxy atom, halogen atom, cyano, tert-butyl, substituted or unsubstituted cycloalkyl, adamantyl, trimethylsilyl, 1,1,4,4-tetramethylcycloalkyl, wherein 1,1,4,4-tetramethylcycloalkyl may form a fused ring with the ring in which it is located.

[0100] Preferably, the specific structural formula of the deuterated boron nitrogen organic compound is any one of the following structures:

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116] An organic electroluminescent device includes a cathode and an anode, and an organic light-emitting functional layer therebetween, the organic light-emitting functional layer including a light-emitting layer containing the aforementioned deuterated boron nitrogen organic compound.

[0117] Preferably, the light-emitting layer comprises a host material and a dopant material, wherein the dopant material contains the aforementioned deuterated boron nitrogen organic compound.

[0118] Preferably, the light-emitting layer comprises a first host material, a second host material, and a dopant material, wherein at least one of the first host material and the second host material is a TADF material, and the dopant material is the aforementioned deuterated boron nitrogen organic compound.

[0119] Preferably, the light-emitting layer comprises a host material, an exciton-sensitizing material, and a dopant material, wherein the exciton-sensitizing material is a complex containing a metal element, and the dopant material is the aforementioned deuterated boron nitrogen organic compound.

[0120] The beneficial technical effects of this invention are as follows:

[0121] (1) The compounds of the present invention can significantly improve device lifespan.

[0122] (2) When phosphorescent dopants are added, the compounds of the present invention can further improve device lifetime;

[0123] (3) When phosphorescent dopants are added, the compounds of the present invention can further improve device efficiency. Attached Figure Description

[0124] Figure 1 This is a schematic diagram of the structure of an OLED device in which the materials listed in this invention are applied;

[0125] Wherein, 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 Implementation

[0126] The technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. Unless otherwise specified, the embodiments and features in the embodiments of the present invention can be combined with each other. The present invention will be further described below with reference to the accompanying drawings and specific embodiments, but this is not intended to limit the present invention.

[0127] In this invention, the terms "upper," "lower," "top," and "bottom," used to describe electrodes, organic electroluminescent devices, and other structures, indicate orientation only in a specific state and do not imply that the structure can only exist in that orientation. Conversely, if the structure can be repositioned, such as by inverting it, the orientation of the structure changes accordingly. Specifically, in this invention, the "bottom" or "lower" side of the electrode refers to the side of the electrode closer to the substrate during fabrication, while the opposite side farther from the substrate is the "top" or "upper" side.

[0128] In this invention, C6-C is substituted or unsubstituted. 30 Aryl refers to substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthrene, substituted or unsubstituted tetraphenyl, substituted or unsubstituted pyrene, substituted or unsubstituted biphenyl, substituted or unsubstituted para-triphenyl, substituted or unsubstituted meta-triphenyl, substituted or unsubstituted The group may be a fused ring consisting of a substituted or unsubstituted triphenyl group, a substituted or unsubstituted peryl group, a substituted or unsubstituted indole group, or a combination of the aforementioned groups, but is not limited thereto.

[0129] In this invention, substituted or unsubstituted C2-C 30Heteroaryl refers to substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted pyrrole, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazine, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted... The fused ring of substituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted naphridyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenthiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fumonyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoleyl, combinations thereof, or combinations of the foregoing groups, but not limited thereto.

[0130] The C1-C of this invention 10 Alkyl groups (including straight-chain alkyl and branched-chain alkyl) refer 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, etc., but are not limited to these.

[0131] The halogen atom mentioned in this invention refers to chlorine atom, fluorine atom or bromine atom, etc., but is not limited to these.

[0132] The C3-C of this invention 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms as cyclic atoms. In this document, C4-C9 cycloalkyl groups are preferred, C5-C8 cycloalkyl groups are more preferred, and C5-C7 cycloalkyl groups are particularly preferred. Non-limiting examples may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl.

[0133] As the substrate for the organic electroluminescent device of this invention, any substrate commonly used in organic electroluminescent devices can be used. Examples include transparent substrates, such as glass or transparent plastic substrates; opaque substrates, such as silicon substrates; and flexible PI film substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Their application varies depending on their properties. In this invention, a transparent substrate is preferred. There are no particular limitations on the thickness of the substrate.

[0134] A first electrode is formed on a substrate, and the first electrode and a second electrode may be opposite 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 Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, or a mixture of metals. The thickness of the first electrode layer depends on the material used, typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.

[0135] 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.

[0136] In this paper, the hole transport region constituting an organic electroluminescent device can be listed as a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0137] As for the materials used in the hole injection layer, hole transport layer, and electron blocking layer, any material can be selected from known materials used in OLED devices.

[0138] Examples of the aforementioned materials include phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridinium derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quinone derivatives, styrene-based anthracene derivatives, styrene-based amine derivatives, styrene compounds, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyaryl alkane derivatives, polyphenylene oxide and its derivatives, polythiophene and its derivatives, poly-N-vinylcarbazole derivatives, thiophene oligomers and other conductive polymers, aromatic tertiary amine compounds, and styrene aminations. Compounds, triamines, tetraamines, benzidines, propyne diamine derivatives, p-phenylenediamine derivatives, m-phenylenediamine derivatives, 1,1'-bis(4-diarylaminophenyl)cyclohexane, 4,4'-bis(diarylamine)biphenyls, bis[4-(diarylamino)phenyl]methanes, 4,4'-bis(diarylamino)terphenyls, 4,4'-bis(diarylamino)tetraphenyls, 4,4'-bis(diarylamino)diphenyl ethers, 4,4'-bis(diarylamino)diphenylsulfanes, bis[4-(diarylamino)phenyl]dimethylmethanes, bis[4-(diarylamino)phenyl]-bis(trifluoromethyl)methanes, or 2,2-diphenylethylene compounds, etc.

[0139] Furthermore, depending on the device configuration requirements, the hole transport film layer between the hole transport auxiliary layer and the hole injection layer of the organic electroluminescent device can be a single film layer or a stacked structure of multiple hole transport materials. In this paper, the film thickness of the various hole carrier conduction films with different functions is not particularly limited.

[0140] The hole injection layer comprises a host organic material capable of conducting holes, and a p-type doped material with a deep HOMO level (correspondingly, a deep LUMO level). Based on empirical observations, to achieve smooth hole injection from the anode to the organic film, the HOMO level of the host organic material used in the anode interface buffer layer must possess certain characteristics with the p-doped material. This is necessary to enable charge transfer states between the host and doped materials, achieve ohmic contact between the buffer layer and the anode, and realize efficient hole injection conduction from the electrode to the hole injection layer.

[0141] Based on the above empirical summary, different P-doped materials need to be selected to match the hole-based host materials of different HOMO energy levels in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0142] Therefore, in one embodiment of the present invention, in order to improve hole injection, the hole injection layer further comprises a p-type dopant material selected from the following charge-conducting materials: quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyl (F4-TCNQ); or hexaazatriphenyl derivatives, such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenyl (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 thereto.

[0143] In the hole injection layer of the present invention, the ratio of hole transport material to P-type doped material is 99:1-95:5, preferably 99:1-97:3, based on mass.

[0144] The thickness of the hole injection layer of the present invention can be 5-100 nm, preferably 5-50 nm and more preferably 5-20 nm, but the thickness is not limited to this range.

[0145] The thickness of the hole transport layer of the present invention can be 5-200 nm, preferably 10-150 nm and more preferably 20-100 nm, but the thickness is not limited to this range.

[0146] The thickness of the electron blocking layer of the present invention can be 1-40 nm, preferably 5-10 nm, but the thickness is not limited to this range.

[0147] After forming the hole injection layer, hole transport layer, and electron blocking layer, a corresponding light-emitting layer is formed on top of the electron blocking layer.

[0148] The light-emitting layer may include a host material and a dopant material. The host material may be a green light host material commonly used in the art, and the dopant material may be a deuterated boron nitrogen organic compound represented by the general formula (1) of this invention.

[0149] In the light-emitting layer of the present invention, the ratio of the host material to the dopant material is 99:1-70:30, preferably 99:1-85:15 and more preferably 97:3-87:13, based on mass.

[0150] The thickness of the light-emitting layer can be adjusted to optimize luminous efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, more preferably 10-50 nm, and even more preferably 15-30 nm, but the thickness is not limited to this range.

[0151] In this 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.

[0152] A hole-blocking layer is a layer that prevents holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby extending the device's lifetime and improving its efficiency. The hole-blocking layer of this invention can be disposed above the light-emitting layer. As the hole-blocking layer material for the organic electroluminescent device of this invention, compounds with hole-blocking properties known in the prior art can be used, such as phenanthroline derivatives like copper hydroxide (BCP), metal complexes of hydroxyquinoline derivatives like aluminum(III)bis(2-methyl-8-quinoline)-4-phenylphenol (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, and pyrimidine derivatives such as 9,9′-(5-(6-([1,1′-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene)bis(9H-carbazole) (CAS No.: 1345338-69-3), etc. The thickness of the hole blocking layer of the present invention can be 2-200 nm, preferably 5-150 nm, but the thickness is not limited to this range.

[0153] An electron transport layer may be disposed above the light-emitting layer or (if present) a hole-blocking layer. The electron transport layer material is one that readily receives electrons from the cathode and transfers the received electrons to the light-emitting layer. Materials with high electron mobility are preferred. As the electron transport layer of the organic electroluminescent device of the present invention, electron transport layer materials known in the prior art for organic electroluminescent devices can be used, such as metal complexes of hydroxyquinoline derivatives represented by Alq3, BAlq and Liq, various rare earth metal complexes, triazole derivatives, triazine derivatives such as 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthyl-2-yl)-1,3,5-triazine (CAS No.: 1459162-51-6), imidazole derivatives such as 2-(4-(9,10-bis(naphthyl-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (CAS No.: 561064-11-7, commonly known as LG201), oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silicon-based compound derivatives, etc. The thickness of the electron transport layer of the present invention can be 10-80 nm, preferably 20-60 nm and more preferably 25-45 nm, but the thickness is not limited to this range.

[0154] An electron injection layer may be disposed above the electron transport layer. The electron injection layer material is typically preferably a material with a low work function, allowing electrons to be easily injected into the organic functional material layer. As the electron injection layer material for the organic electroluminescent device of the present invention, electron injection layer materials known in the art for organic electroluminescent devices can be used, such as lithium; lithium salts, such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate, or lithium azide; or cesium salts, such as cesium fluoride, cesium carbonate, or cesium azide. 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.

[0155] The second electrode may be disposed above the electron transport region. The second electrode may be a cathode. The second electrode may be a transmission electrode, a semi-transmission electrode, or a reflection electrode. When the second electrode is a transmission electrode, it may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF, Ba, Ag, or compounds or mixtures thereof; when the second electrode is a semi-transmission electrode or a reflection electrode, it may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or compounds or mixtures thereof, but is not limited thereto. The thickness of the cathode depends on the material used, typically 10-50 nm, preferably 15-20 nm.

[0156] The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure preventing external 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 or metal can; or a thin film covering the entire surface of the organic layer.

[0157] The method for preparing the organic electroluminescent device of the present invention includes sequentially 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, and optionally a capping layer, onto a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI can be used, but are not limited thereto. In the present invention, vacuum evaporation is preferably used to form the various layers. Those skilled in the art can conventionally select the various process conditions in the vacuum evaporation method according to actual needs.

[0158] All raw materials involved in the synthesis embodiments of the present invention can be purchased from the market or prepared by conventional preparation methods in the art.

[0159] Synthesis of compound-4:

[0160]

[0161] Synthesis of raw material-1a:

[0162] Add ingredient-2b (10g, 36mmol), ingredient-1m (12.45g, 36mmol), and C to the bottle. s2 CO3 (35.0 g, 107 mmol), DMF (150 mL), followed by nitrogen protection, stirred overnight at 120 °C. After the reaction was complete, the mixture was cooled, and ethyl acetate was added to dilute the reaction solution. The mixture was filtered, and the organic phase was washed with saturated sodium chloride, dried over anhydrous sodium sulfate, concentrated, and pulped to obtain crude product -1a. This crude product was then separated by silica gel column chromatography. LCMS determination: 498.26 (M+H). + LCMS theoretical value: 497.11.

[0163] Synthesis of raw material -1c:

[0164] Add starter-1a (10 g, 20 mmol) and anhydrous THF (100 mL) to the flask, then under nitrogen protection, cool to -78 °C, add n-butyllithium (22 mmol, 2.5 M), then heat to -10 °C and stir for 2 h. Add starter-1b (3.8 g, 20 mmol), and continue stirring overnight at room temperature. Quench with ammonium chloride aqueous solution, extract with ethyl acetate, wash with saturated sodium chloride, dry over anhydrous sodium sulfate, concentrate, and separate by silica gel column chromatography to obtain starter-1c. LCMS determination: 608.41 (M+H). +LCMS theoretical value: 607.31.

[0165] Synthesis of raw material - 1d:

[0166] Anhydrous dichloromethane (1.0 L) and starting material -1c (5.2 g, 9.0 mmol) were added to the reaction flask under nitrogen protection. Then, boron trifluoride diethyl ether solution (2 mL, 48%) was added, and the mixture was stirred at room temperature for 1 h. After the reaction was complete, the mixture was directly concentrated and then separated by silica gel column chromatography to obtain starting material -1d. LCMS determination: 590.38 (M+H) + LCMS theoretical value: 589.30.

[0167] Synthesis of raw material-1f:

[0168] Add reactants -1d (2.80 g, 4.8 mmol), -1e (1.71 g, 4.8 mmol), CuI (0.01 g, 0.5 mmol), cesium carbonate (5.0 g, 15 mmol), and NMP (60 mL) sequentially to the reaction flask under nitrogen protection. Stir overnight at 150 °C. After the reaction is complete and cooled to room temperature, dilute the reaction solution with ethyl acetate, wash with saturated brine to remove NMP, dry the organic phase with anhydrous sodium sulfate, concentrate, and separate by silica gel column chromatography to obtain reactant -1f. LCMS determination: 853.45 (M+H) + LCMS theoretical value: 852.47.

[0169] Preparation of raw material - 1g:

[0170] The following reagents were added sequentially to the reaction flask: 1f (2.2 g, 2.58 mmol), Pd₂(dba)₃ (230 mg, 0.25 mmol), S-phos (210 mg, 0.5 mmol), potassium tert-butoxide (0.4 g, 3.5 mmol), and toluene (50 mL). The mixture was then refluxed and stirred overnight under nitrogen protection. After the reaction was complete, the mixture was cooled to room temperature, diluted with ethyl acetate, washed with saturated brine, concentrated, and separated by silica gel column chromatography to obtain 1g of the reactant. LCMS determination: 817.44 (M+H). + LCMS theoretical value: 816.49.

[0171] Preparation of raw materials - 1 hour:

[0172] Add 1 g (16.0 g, 19.5 mmol) of raw material and 200 mL of DMF sequentially to the reaction flask; under nitrogen protection, cool to -10 °C, dissolve 4.0 g of NBS in 50 mL of DMF, then add the NBS-DMF solution to the flask, and stir overnight at 50 °C in the dark. After the reaction is complete, cool and dilute the reaction solution with ethyl acetate, wash away the DMF with saturated brine, concentrate, and slurry with ethyl acetate / petroleum ether, then wash with methanol to obtain the raw material -1 h. LCMS determination: 895.41 (M+H) + LCMS theoretical value: 894.40.

[0173] Preparation of compound-4:

[0174] The starting material (5 g, 5.6 mmol) and anhydrous o-dichlorobenzene (100 mU) were added sequentially to the reaction flask. The mixture was cooled to -78 °C under nitrogen protection, and n-BuLi (8.5 mmol, 2.5 M) was added. The mixture was then stirred at room temperature for one hour. BBr3 (4.2 g, 16.5 mmol) was added at -40 °C, followed by DIPEA (2.5 mL, 15 mmol). The mixture was then stirred overnight at 150 °C. The reaction was quenched with a saturated sodium bicarbonate solution, extracted with dichloromethane, and the organic phase was concentrated and purified by silica gel column chromatography to obtain compound 4. LCMS determination: 825.49 (M+H). + LCMS theoretical value: 824.48.

[0175] Preparation of compound-51:

[0176]

[0177]

[0178] Preparation of raw material - 2g:

[0179] Add reactant-2m (15 g, 52 mmol), reactant-2n (12.8 g, 52 mmol), and THF (300 mL) sequentially to the reaction flask. Under nitrogen protection, add LiHDMS (13.0 g, 77 mmol), tri-tert-butylphosphine (2.1 g, 10.4 mmol), and Pd₂(dba)₃ (2.3 g, 2.6 mmol) at 0 °C. Stir overnight at 70 °C, quench with saturated sodium chloride, extract with ethyl acetate, wash with saturated sodium chloride, dry over anhydrous sodium sulfate, concentrate, and separate by silica gel column chromatography to obtain reactant-2g. LCMS determination: 455.47 (M+H). + LCMS theoretical value: 454.32.

[0180] Preparation of raw material -2c:

[0181] The following reactants were added sequentially to a reaction flask: reactant-2a (16.7 g, 50 mmol), reactant-2b (14.0 g, 50 mmol), Pd2(dba)3 (1.0 g, 1.1 mmol), S-phos (0.9 g, 2.2 mmol), potassium carbonate (20.7 g, 150 mmol), and toluene (500 mL). The mixture was then refluxed and stirred overnight under nitrogen protection. After the reaction was complete, the mixture was cooled to room temperature and diluted with ethyl acetate. The solution was washed with saturated brine, concentrated, and separated by silica gel column chromatography to obtain reactant-2c. LCMS determination: 486.15 (M+H)+; LCMS theoretical value: 485.09.

[0182] Preparation of raw material -2e:

[0183] Add starting material -2c (9.74 g, 20 mmol) and anhydrous THF (150 mL) sequentially to the reaction flask. Under nitrogen protection, cool to -78 °C, add n-butyllithium (9 mL, 22.5 mmol, 2.5 M), then heat to -10 °C and react for two hours. Add starting material -2d (5.85 g, 20 mmol), continue stirring overnight at room temperature, quench with ammonium chloride aqueous solution, extract with ethyl acetate, wash with saturated sodium chloride, dry over anhydrous sodium sulfate, concentrate, and separate by silica gel column chromatography to obtain starting material -2e. LCMS determination: 700.41 (M+H) + LCMS theoretical value: 699.36.

[0184] Preparation of raw material-2f:

[0185] The starting material -2e (10.0 g, 14.3 mmol), anhydrous dichloromethane (900 mL), and boron trifluoride diethyl ether solution (4 mL, 48%) were added sequentially to the reaction flask under nitrogen protection. The mixture was stirred at room temperature for 2 h. After the reaction was completed, the solution was directly evaporated to dryness, and the starting material -2f was obtained by silica gel column chromatography. LCMS determination: 682.43 (M+H) + LCMS theoretical value: 681.35.

[0186] Preparation of raw materials - 2h:

[0187] Add reactant-2f (6.8 g, 10 mmol), reactant-2g (4.53 g, 10 mmol), cesium carbonate (9.77 g, 30 mmol), and DMF (180 mL) sequentially to the reaction flask. Under nitrogen protection, stir overnight at 120 °C. After the reaction is complete, cool and dilute with ethyl acetate. Wash with saturated brine, dry to anhydrous sodium sulfate, concentrate, and separate by silica gel column chromatography to obtain reactant-2h. LCMS determination: 1116.75 (M+H). + LCMS theoretical value: 1115.67.

[0188] Preparation of compound-51:

[0189] The starting material (10.3 g, 9.22 mmol) and anhydrous o-dichlorobenzene (140 mL) were added sequentially to the reaction flask. The mixture was cooled to -78 °C under nitrogen protection, and t-BuLi (12 mL, 1.3 M) was added. The mixture was then stirred at room temperature for one hour. BBr3 (7.0 g, 28.0 mmol) was added at -40 °C, followed by DIPEA (5 mL, 30 mmol). The mixture was then stirred overnight at 150 °C. The reaction was quenched with saturated sodium bicarbonate solution, extracted with dichloromethane, and the organic phase was concentrated and purified by silica gel column chromatography to obtain compound -51. LCMS determination: 1090.65 (M+H). + LCMS theoretical value: 1089.69.

[0190] Preparation of compound-60:

[0191]

[0192] Preparation of raw material -3C:

[0193] Add reactant 3a (20 g, 62.5 mmol), reactant-3b (37.2 g, 125.5 mmol), cesium carbonate (61.0 g, 188 mmol), and DMF (300 mL) sequentially to the reaction flask. Under nitrogen protection, stir overnight at 120 °C. After the reaction is complete, cool and dilute with ethyl acetate. Wash with saturated brine, dry to anhydrous sodium sulfate, concentrate, and separate by silica gel column chromatography to obtain reactant-3c; LCMS value: 873.46 (M+H). + LCMS theoretical value: 872.45.

[0194] Preparation of raw material -3e:

[0195] Add 10 g (11.4 mmol) of starter-3c and 150 mL of anhydrous THF to a flask, then under nitrogen protection, cool to -78 °C, add 7 mL (2.5 M) of n-butyllithium, then heat to -10 °C and stir for 2 h. Add 2.1 g (11.5 mmol) of starter-3d, and continue stirring overnight at room temperature. Quench with ammonium chloride aqueous solution, extract with ethyl acetate, wash with saturated salt, dry over anhydrous sodium sulfate, concentrate, and separate by silica gel column chromatography to obtain starter-3e; LCMS value: 927.83 (M+H). + LCMS theoretical value: 926.61.

[0196] Preparation of raw material -3f:

[0197] Anhydrous dichloromethane (900 mL) and starting material -3e (16 g, 17.2 mmol) were added to the reaction flask under nitrogen protection. Then, boron trifluoride diethyl ether solution (4 mL, 48%) was added, and the mixture was stirred at room temperature for 1 h. After the reaction was complete, the mixture was directly concentrated and then separated by column chromatography to obtain starting material -3f; LCMS value: 909.63 (M+H). + LCMS theoretical value: 908.60.

[0198] Preparation of compound-60:

[0199] The starting material -3f (5.0 g, 5.5 mmol) and anhydrous o-dichlorobenzene (100 mL) were added sequentially to the reaction flask. The mixture was cooled to -78 °C under nitrogen protection, and n-BuLi (3.3 mL, 2.5 M) was added. The mixture was then stirred at room temperature for one hour. BBr3 (4.2 g, 16.5 mmol) was added at -40 °C, followed by DIPEA (5 mL, 18 mmol). The mixture was then stirred overnight at 150 °C. The reaction was quenched with a saturated sodium bicarbonate solution, extracted with dichloromethane, and the organic phase was concentrated and purified by silica gel column chromatography to obtain compound -60. LCMS determination: 839.65 (M+H). + LCMS theoretical value: 838.67.

[0200] Preparation of compound-105:

[0201]

[0202] The preparation of compound-105 is referenced to that of compound-60: the characterization of the intermediates is as follows:

[0203] Raw material - 4b, LCMS measurement: 885.53 (M+H) + LCMS theoretical value: 884.52.

[0204] Raw material - 4c, LCMS measurement: 1051.77 (M+H) + LCMS theoretical value: 1050.81.

[0205] Raw material - 4 days, LCMS measurement: 1032.83 (M+H) + LCMS theoretical value: 1031.79.

[0206] Compound-105, LCMS value: 960.93 (M+H) + LCMS theoretical value: 959.85.

[0207] Preparation of compound-134:

[0208]

[0209] Preparation of raw material -5c:

[0210] The following reactants were added sequentially to a reaction flask: reactant-5a (25.0 g, 65.8 mmol), reactant-5b (18.5 g, 65.8 mmol), Pd₂(dba)₃ (1.2 g, 1.3 mmol), S-phos (1.06 g, 2.6 mmol), potassium carbonate (28.0 g, 200 mmol), and toluene (500 mL). The mixture was then refluxed and stirred overnight under nitrogen protection. After the reaction was complete, the mixture was cooled to room temperature, diluted with ethyl acetate, washed with saturated brine, concentrated, and separated by silica gel column chromatography to obtain reactant-5c. LCMS determination: 532.45 (M+H). + LCMS theoretical value: 531.06.

[0211] Preparation of raw material - 5d:

[0212] Add reactant-5c (15 g, 28.1 mmol), reactant-2b (7.86 g, 28.1 mmol), cesium carbonate (27.5 g, 84.5 mmol), and DMF (300 mL) sequentially to the reaction flask. Under nitrogen protection, stir overnight at 120 °C. After the reaction is complete, cool and dilute the reaction solution with ethyl acetate. Wash with saturated brine, dry to anhydrous sodium sulfate, evaporate to dryness, and separate by silica gel column chromatography to obtain reactant-5d. LCMS determination: 791.34 (M+H). + LCMS theoretical value: 790.25.

[0213] Preparation of raw material -5f:

[0214] Add starter-5d (10 g, 12.6 mmol) and anhydrous THF (150 mL) to the flask, then under nitrogen protection, cool to -78 °C, add n-butyllithium (7.5 mL, 2.5 M), then heat to -10 °C and stir for 2 h. Add starter-1b (4.74 g, 25.2 mmol), and continue stirring overnight at room temperature. Quench with ammonium chloride aqueous solution, extract with ethyl acetate, wash with saturated sodium chloride, dry over anhydrous sodium sulfate, concentrate, and separate by silica gel column chromatography to obtain starter-5f. LCMS determination: 1011.58 (M+H) + LCMS theoretical value: 1010.64.

[0215] Preparation of raw materials - 5h:

[0216] Add reactant -5f (8.0 g, 7.9 mmol), anhydrous dichloromethane (900 mL), and boron trifluoride diethyl ether solution (2 mL, 48%) sequentially to the reaction flask under nitrogen protection. Stir at room temperature for 2 hours. After the reaction is complete, evaporate to dryness and separate reactant -5f by silica gel column chromatography. LCMS determination: 975.57 (M+H) + LCMS theoretical value: 974.62.

[0217] Preparation of raw material-5j:

[0218] Add starting material -5j (7.9 g, 8.1 mmol) and DMF (150 mL) sequentially to the reaction flask; under nitrogen protection, cool to -10 °C, dissolve NBS (1.6 g) in DMF (50 mL), then add the NBS DMF solution to the flask, and stir overnight at 50 °C in the dark. After the reaction is complete, cool and dilute the reaction solution with ethyl acetate, wash with saturated brine, concentrate, and slurry with ethyl acetate / petroleum ether, then wash with methanol to obtain starting material -5j. LCMS determination: 1053.64 (M+H) + LCMS theoretical value: 1052.53.

[0219] Preparation of compound-134:

[0220] The starting material -5j (6.3 g, 6.0 mmol) and anhydrous o-dichlorobenzene (100 mL) were added sequentially to the reaction flask. Under nitrogen protection, the mixture was cooled to -78 °C, and n-BuLi (3.5 mL, 2.5 M) was added. The mixture was then stirred at room temperature for one hour. At -40 °C, BBr3 (4.5 g, 18.0 mmol) and DIPEA (5 mL, 18 mmol) were added, followed by stirring at 150 °C overnight. The reaction was quenched with saturated sodium bicarbonate solution, extracted with dichloromethane, and the organic phase was concentrated and purified by silica gel column chromatography to obtain compound -134. LCMS determination: 983.71 (M+H). + LCMS theoretical value: 982.61.

[0221] Preparation of compound-233:

[0222]

[0223] Preparation of compound-233: The preparation was carried out in accordance with Examples 1 and 2, and the characterization involved is as follows:

[0224] Raw material - 6b, LCMS measurement: 498.23 (M+H) + LCMS theoretical value: 497.11.

[0225] Raw material - 6c, LCMS measurement: 608.30 (M+H)+ LCMS theoretical value: 607.31.

[0226] Raw material - 6 days, LCMS measurement: 590.48 (M+H) + LCMS theoretical value: 589.30.

[0227] Raw material - 6f, LCMS determination: 890.46 (M+H) + LCMS theoretical value: 889.39.

[0228] Compound-233, LCMS value: 864.49 (M+H) + LCMS theoretical value: 863.42.

[0229] Preparation of compound-82:

[0230]

[0231] Preparation of compound-82: The preparation was carried out in accordance with Examples 1 and 2, and the characterization involved is as follows:

[0232] Raw material - 7f, LCMS determination: 758.33 (M+H) + LCMS theoretical value: 757.30.

[0233] Compound-82, LCMS value: 732.41 (M+H) + LCMS theoretical value: 731.33.

[0234] Preparation of compound-236:

[0235]

[0236] The synthesis of compound-236 is described in Example-5:

[0237] Raw material -8b, LCMS measured value: 801.44(M+H)+; LCMS theoretical value: 800.31.

[0238] Raw material -8c, LCMS measured value: 1021.79(M+H)+; LCMS theoretical value: 1020.70.

[0239] Raw material - 8d, LCMS measured value: 983.68(M+H)+; LCMS theoretical value: 982.67.

[0240] Raw material -8e, LCMS measured value: 1061.64(M+H)+; LCMS theoretical value: 1060.58.

[0241] Compound-236, LCMS measured value: 989.62 (M+H)+; LCMS theoretical value: 988.64.

[0242] Preparation of compounds-283 and-285:

[0243]

[0244] The preparation of compound-283 is described in reference to the synthesis of compound-236.

[0245] Raw material -9b, LCMS measured value: 939.77(M+H)+; LCMS theoretical value: 938.68.

[0246] Raw material -9c, LCMS measured value: 918.67(M+H)+; LCMS theoretical value: 917.65.

[0247] Compound-283, LCMS measured value: 848.79 (M+H)+; LCMS theoretical value: 847.73.

[0248] The synthesis of raw material -9e is referenced from the synthesis of raw material -5j:

[0249] Raw material -9e, LCMS measured value: 926.75(M+H)+; LCMS theoretical value: 925.64.

[0250] Synthesis of compound-285:

[0251] The following compounds were added sequentially to the flask: starting material -9e (4.5 g, 4.9 mmol), toluene (80 mL), tetrakis(triphenylphosphine)palladium (1.2 g, 1.0 mmol), starting material -9d (0.87 g, 4.9 mmol), potassium carbonate (2.7 g, 20 mmol), water (10 mL), and ethanol (30 mL); the mixture was then refluxed overnight under nitrogen protection; after the reaction was completed, the mixture was cooled, quenched with water, extracted with dichloromethane, and the combined organic phases were separated by silica gel column chromatography to give compound -285. LCMS determination: 981.95 (M+H)+; LCMS theoretical value: 980.82.

[0252] Preparation of compound-286:

[0253]

[0254] The synthesis of compound-286 is referenced from the synthesis of compound-285:

[0255] Compound-286, LCMS measured value: 981.85(M+H)+; LCMS theoretical value: 980.82.

[0256] Preparation of compound-250:

[0257]

[0258] The synthesis of compound-250 is referenced from the synthesis of compound-236:

[0259] Raw material -11b, LCMS measured value: 837.61(M+H)+; LCMS theoretical value: 836.54.

[0260] Raw material -11c, LCMS measured value: 1041.97(M+H)+; LCMS theoretical value: 1040.83.

[0261] Raw material - 11d, LCMS measured value: 1003.85(M+H)+; LCMS theoretical value: 1002.80.

[0262] Raw material -11e, LCMS measured value: 1081.89(M+H)+; LCMS theoretical value: 1080.71.

[0263] Compound-250, LCMS measured value: 1009.72 (M+H)+; LCMS theoretical value: 1008.77.

[0264] Device Example 1

[0265] like Figure 1As shown, the transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), followed by washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues from the transparent ITO surface. After the above washing, HT-1 and HI-1 with a thickness of 10nm are deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 60nm thick layer of HT-1 is deposited as a hole transport layer 4. Subsequently, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking materials are deposited, the light-emitting layer 6 of the OLED light-emitting device is fabricated, using GH-1 and GH-2 as the host materials and compound-4 as the dopant material, with a mass ratio of GH-1, GH-2, and compound-4 of 69:30:1, and a film thickness of 30nm. Following the aforementioned light-emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer serves as the hole-blocking layer 7. Following the hole-blocking layer 7, ET-1 and Liq are vacuum-deposited at a mass ratio of 1:1, resulting in a film thickness of 30 nm; this layer serves as the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer serves as the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 80 nm is fabricated using a vacuum evaporation apparatus, with a Mg:Ag mass ratio of 1:9; this layer serves as the cathode layer 10.

[0266] The application effects of the OLED material synthesized in this invention in devices are described in detail below through device examples 1-12 and device comparative examples 1-2. The fabrication processes of device examples 1-12 are completely identical to those of device comparative examples 1-2, and the same substrate and electrode materials are used, with the electrode film thickness remaining consistent. The only difference is the replacement of the light-emitting layer material in the device. The layer structures and test results of each device example are shown in Tables 6 and 7, respectively.

[0267] Device Example 8

[0268] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), followed by washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues from the transparent ITO surface. After the above washing, a 10nm thick layer of HT-1 and HI-1 is deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 60nm thick layer of HT-1 is deposited as a hole transport layer 4. Finally, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking material is deposited, the emitting layer 6 of the OLED light-emitting device is fabricated. GH-1 and GH-2 are used as the host materials, GD-1 as the first dopant, and Compound-4 as the second dopant. The mass ratio of GH-1, GH-2, GD-1, and Compound-4 is 66:30:3:1, and the thickness of the emitting layer is 30 nm. After the emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer is the hole blocking layer 7. After the hole blocking layer 7, ET-1 and Liq are vacuum-deposited to a mass ratio of 1:1, with a thickness of 30 nm; this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 80 mm is fabricated using a vacuum evaporation apparatus; the mass ratio of Mg to Ag is 1:9; this layer is used as the cathode layer 10.

[0269] The application effects of the OLED material synthesized in this invention in devices are described in detail below through device examples 13-24 and device comparative examples 3-4. The fabrication processes of device examples 13-24 are exactly the same as those of device comparative examples 3-4, and the same substrate and electrode materials are used, with the same electrode film thickness. The only difference is the replacement of the light-emitting layer material in the device. The layer structures and test results of each device example are shown in Tables 6 and 7, respectively.

[0270] The molecular structural formulas of the relevant materials are shown below:

[0271]

[0272] Compounds ref-1 and ref-2 were prepared according to methods described in the prior art.

[0273] After completing the OLED light-emitting device as described above, the anode and cathode are connected using a known driving circuit, and the device's voltage, current efficiency, and lifetime are measured. Examples and comparative examples of devices prepared using the same method are shown in Table 6; the test results for the voltage, current efficiency, and lifetime of the obtained devices are shown in Table 7.

[0274] Table 6

[0275]

[0276]

[0277] Table 7

[0278]

[0279] Note: Current efficiency and emission peak were measured using an IVL (current-voltage-brightness) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.); the lifetime testing system was the EAS-62C OLED device lifetime tester from System Technology Inc., Japan; LT95 refers to the time it takes for the device brightness to decay to 95%; all data were measured at 10mA / cm2.

[0280] As can be seen from the device data results in Table 7, compared with devices in Comparative Examples 1-2, the device lifetime of the compounds in the examples in the single-doped system was significantly improved; the device efficiency also showed a better effect.

[0281] In the device system incorporating GD-1 (dual-doped system), the lifetime of the compound in the examples was also significantly improved compared to devices in Comparative Examples 3-4. Compared to the single-doped system, the dual-doped system exhibited outstanding performance improvements in both efficiency and lifetime.

[0282] In summary, the above are merely 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 within the protection scope of the present invention.

Claims

1. A deuterated boron nitrogen organic compound, characterized in that, The structures of the deuterated boron nitrogen organic compounds are shown in general formulas (2-8), (2-9), or (2-12): R1-R 31 Each instance of the same or different element is represented by a hydrogen atom, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, phenyl-substituted amino groups, tert-butylbenzene-substituted amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; In general formula (2-8), R1-R 21 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom; In general formula (2-9), R1-R 31 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom; In general formula (2-12), R1-R 29 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom; The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl groups, C3-C 10 cycloalkyl, C6-C 30 Aryl, C2~C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N, Si, and B.

2. A deuterated boron nitrogen organic compound, characterized in that, The structures of the deuterated boron nitrogen organic compounds are shown in general formulas (2-10) to (2-11): R1-R 22 Each instance of the same or different element is represented by a hydrogen atom, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, phenyl-substituted amino groups, tert-butylbenzene-substituted amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; In general formulas (2-10) and (2-11), R1-R 22 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom; X represents one of O and S; Y represents one of O and S; The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl groups, C3-C 10 cycloalkyl, C6-C 30 Aryl, C2~C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N, Si, and B.

3. The deuterated boron nitrogen organic compound according to claim 1 or 2, characterized in that, The R 13 -R 20 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom.

4. The deuterated boron nitrogen organic compound according to claim 1, characterized in that, The R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 21 R 22 R 23 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom.

5. The deuterated boron nitrogen organic compound according to claim 1 or 2, characterized in that, The R2, R3, R4, R5, R6, R7, R8, R9, R 10 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom.

6. The deuterated boron nitrogen organic compound according to claim 1 or 2, characterized in that, The R3, R6, R9, R 10 R 21 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom.

7. The deuterated boron nitrogen organic compound according to claim 1 or 2, characterized in that, The R3, R6, R9, R 21 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom.

8. The deuterated boron nitrogen organic compound according to claim 1 or 2, characterized in that, At least one of R3 and R6 represents a deuterium atom or a group substituted by a deuterium atom.

9. The deuterated boron nitrogen organic compound according to claim 1 or 2, characterized in that, The R 13 -R 20 The 1, 2, 3, 4, 5, 6, 7, or 8 in the text represent deuterium atoms or groups substituted by deuterium atoms.

10. The deuterated boron nitrogen organic compound according to claim 1, characterized in that, The R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 21 R 22 R 23 The 1, 2, 3, 4, 5, 6, 7, or 8 in the text represent deuterium atoms or groups substituted by deuterium atoms.

11. The deuterated boron nitrogen organic compound according to claim 1 or 2, characterized in that, The R2, R3, R4, R5, R6, R7, R8, R9, R 10 The 1, 2, 3, 4, 5, 6, 7, or 8 in the text represent deuterium atoms or groups substituted by deuterium atoms.

12. The deuterated boron nitrogen organic compound according to claim 1 or 2, characterized in that, The R3, R6, R9, R 10 R 21 The 1, 2, 3, 4, or 5 in the text represent deuterium atoms or groups substituted by deuterium atoms.

13. The deuterated boron nitrogen organic compound according to claim 1 or 2, characterized in that, The R3, R6, R9, R 21 The 1, 2, 3, or 4 in the text represent deuterium atoms or groups substituted by deuterium atoms.

14. The deuterated boron nitrogen organic compound according to claim 1 or 2, characterized in that, One or two of R3 and R6 represent deuterium atoms or groups substituted by deuterium atoms.

15. A deuterated boron nitrogen organic compound, characterized in that, The structure of the deuterated boron nitrogen organic compound is shown in general formula (3-3): The tert-butyl group in general formula (3-3) can be replaced by deuterium; R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 R 15 R 16 R 17 R 18 R 20 Each instance of the same or different element is represented by a hydrogen atom, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, phenyl-substituted amino groups, tert-butylbenzene-substituted amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; In general formula (3-3), R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 R 15 R 16 R 17 R 18 and R 20 At least one of them is represented as a deuterium atom or a group substituted by a deuterium atom; Ra indicates a substituted or unsubstituted phenyl group; Ra and R 12 The benzene ring is linked together by substituted or unsubstituted fluorene groups; The substituents used for the substituent groups are optionally selected from deuterium atoms, halogen atoms, C1 to C2 atoms. 10 Alkyl groups, C3-C 10 cycloalkyl, C6-C 30 Aryl, C2~C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

16. The deuterated boron nitrogen organic compound according to claim 15, characterized in that, The R2, R4, R5, R7, R 13 R 15 -R 18 R 20 At least four of them are represented as deuterium atoms.

17. The deuterated boron nitrogen organic compound according to claim 1, characterized in that, The substituted or unsubstituted C6-C 30 Aryl refers to substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthrene, substituted or unsubstituted tetraphenyl, substituted or unsubstituted pyrene, substituted or unsubstituted biphenyl, substituted or unsubstituted para-triphenyl, substituted or unsubstituted meta-triphenyl, substituted or unsubstituted alkyl, substituted or unsubstituted triphenylene, substituted or unsubstituted perylene, substituted or unsubstituted indole; The substituted or unsubstituted C2-C 30 Heteroaryl refers to substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted pyrrole, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazine, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, and substituted or unsubstituted benzene. Imidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted naphthinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted benzazinyl, substituted or unsubstituted benzathiazinyl, substituted or unsubstituted benzazinyl, substituted or unsubstituted fumonyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl; The C1-C 10 Alkyl groups refer 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, and 1-butylpentyl. The halogen atom mentioned refers to a chlorine atom, a fluorine atom, or a bromine atom; The C3-C 10 Cycloalkyl refers to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl.

18. The deuterated boron nitrogen organic compound according to claim 1, characterized in that, The R1-R 31 Each of these can be independently represented as a hydrogen atom, deuterium atom, fluorine atom, cyano, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, N-phenylcarbazole, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl. One of the following: isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazineyl, methoxy, and tert-butoxy.

19. The deuterated boron nitrogen organic compound according to claim 2, characterized in that, The R1-R 22 Each of these can be independently represented as a hydrogen atom, deuterium atom, fluorine atom, cyano, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, N-phenylcarbazole, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl. One of the following: isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazineyl, methoxy, and tert-butoxy.

20. The deuterated boron nitrogen organic compound according to claim 1, characterized in that, The R1-R 31 Each can be represented independently as shown in the following structure: Hydrogen atom, deuterium atom, Any one of them.

21. The deuterated boron nitrogen organic compound according to claim 2, characterized in that, The R1-R 22 Each can be represented independently as shown in the following structure: Hydrogen atom, deuterium atom, Any one of them.

22. A deuterated boron nitrogen organic compound, characterized in that, The specific structural formula of the deuterated boron nitrogen organic compound is any one of the following structures:

23. An organic electroluminescent device, comprising a cathode and an anode, and an organic light-emitting functional layer therebetween, said organic light-emitting functional layer comprising a light-emitting layer, characterized in that, The light-emitting layer contains the deuterated boron nitrogen organic compound as described in any one of claims 1-22.

24. The organic electroluminescent device according to claim 23, characterized in that, The light-emitting layer comprises a host material and a dopant material, wherein the dopant material contains a deuterated boron nitrogen organic compound as described in any one of claims 1-22.

25. The organic electroluminescent device according to claim 23, wherein the light-emitting layer comprises a first host material, a second host material, and a dopant material, characterized in that, At least one of the first and second main materials is a TADF material, and the doping material is a deuterated boron nitrogen organic compound as described in any one of claims 1-22.

26. The organic light-emitting device according to claim 23, wherein the light-emitting layer comprises a host material, an exciton-sensitizing material, and a dopant material, characterized in that, The exciton sensitizing material is a complex containing a metal element, and the doping material is a deuterated boron nitrogen organic compound as described in any one of claims 1-22.

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