Boron-nitrogen compound and organic electroluminescent device using same

Abstract

The invention provides a boron-nitrogen compound and an organic electroluminescent device using the same, and relates to the technical field of organic electroluminescence. The boron-nitrogen compound provided by the invention has high color purity and high reverse intersystem crossing rate. A rigid group is introduced to a central benzene ring, so that the molecular vibration relaxation is reduced, the FWHM is reduced, and the color purity is improved; meanwhile, derivative donors containing heteroatom phenoxazine or phenothiazine and the like are introduced, spin-orbit coupling is promoted by utilizing a heavy atom effect, so that the reverse intersystem crossing rate of excitons from a triplet state to a singlet state is increased, and the triplet state exciton extinguishing process is weakened. In addition, a large-volume peripheral substituent group is introduced to inhibit aggregation among molecules, so that a mutual quenching phenomenon among the molecules is weakened, and the luminous efficiency is improved. Therefore, when the compound is applied to the organic electroluminescent device, the color purity and luminous efficiency of the organic electroluminescent device can be improved.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic electroluminescence, in particular to a boron-nitrogen compound and an organic electroluminescence device using the same. BACKGROUND

[0002] Organic light emitting diode (OLED) has been widely concerned due to its advantages such as ultra-thin, ultra-light, flexibility, and foldability. In recent years, OLED has developed rapidly and has become a backbone in the field of small and medium-sized display. As the core of OLED, the design and synthesis of organic light emitting material is crucial. Compared with traditional fluorescent materials, pure organic thermally activated delayed fluorescence (TADF) material can convert triplet excitons into singlet excitons to improve the utilization rate of excitons, and theoretically can achieve an internal quantum efficiency (IQE) close to 100%, which has become a research hotspot in recent years.

[0003] In TADF materials, the donor-acceptor (D-A) structure is usually constructed to effectively separate the highest occupied orbital (HOMO) and the lowest unoccupied orbital (LUMO), reduce the anti-intermolecular energy level difference (ΔEST), and facilitate the conversion of triplet excitons to singlet excitons, thereby inducing light emission. However, this molecular structure increases the structural relaxation of the excited state molecule, resulting in a large Stokes shift, which makes the full width at half maximum (FWHM) of the emission spectrum usually reach 50-100 nm. Before commercial application, we can use a filter or an optical microcavity to improve the color purity and obtain excellent CIE color coordinates, but this will reduce the energy utilization rate and make the device manufacturing process more complex. However, MR-TADF based on boron-nitrogen resonance-induced TADF materials (MR-TADF) can induce resonance effects due to the specific position of boron atoms and nitrogen atoms in the rigid structure, so that the material has high color purity and light emission efficiency while having TADF characteristics. Currently, there are few reports on MR-TADF, so it is necessary to further develop new MR-TADF materials and prepare high-efficiency OLEDs. SUMMARY

[0004] To solve the above problems, the present application aims to provide a boron-nitrogen compound and an organic electroluminescence device using the same, which can improve the light emission efficiency and color purity of the light emission spectrum of the organic electroluminescence device.

[0005] The present application provides a boron-nitrogen compound, which is selected from the structure represented by formula I:

[0006]

[0007] The X1 and X2 that are the same or different are selected from single bonds, O, S, Se, N(R) a ), C(R b R b '), Si(R) b R b '), Ge(R) b R b One of the following, and at least one of X1 and X2 is not selected from single bonds;

[0008] The R a It is selected from any one of the following: substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C60 aryl groups, substituted or unsubstituted C2-C60 heteroaryl groups, fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings;

[0009] The R b R b 'The same or different from any one selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring; or R b R b The ' bonds can bond together to form substituted or unsubstituted rings;

[0010] The w atoms, whether identical or different, are selected from C(R1) or N atoms;

[0011] The R1 is selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring; or two adjacent R1s can be bonded to form a substituted or unsubstituted ring;

[0012] The R0 is selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring;

[0013] The Ar1 is selected from the structure shown in formula a-1;

[0014] The X3 is selected from single bonds, O, S, Se, N(R) c ), C(R d R d '), Si(R) d R d '), Ge(R) d R d One of the following;

[0015] The R c It is selected from any one of the following: substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C60 aryl groups, substituted or unsubstituted C2-C60 heteroaryl groups, fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings;

[0016] The R d R d 'The same or different from any one selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring; or R d R d The ' bonds can bond together to form substituted or unsubstituted rings;

[0017] The same or different v is selected from C(R2) or N atoms;

[0018] R2is selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C2-C60 heteroaryl group, substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C6-C60 aromatic ring, and substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C2-C60 heteroaromatic ring;

[0019] R3is selected from any one of substituted or unsubstituted silyl group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C2-C60 heteroaryl group, substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C6-C60 aromatic ring, and substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C2-C60 heteroaromatic ring, or the corresponding N atom of R3is a site bonded to L1;

[0020] Ar2is selected from any one of cyano, halogen, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C2-C60 heteroaryl group, substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C6-C60 aromatic ring, and substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C2-C60 heteroaromatic ring;

[0021] L1and L2are the same or different and are selected from one of single bond, substituted or unsubstituted C6-C60 arylene group, substituted or unsubstituted C2-C60 heteroarylene group, substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C6-C60 aromatic ring, and substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C2-C60 heteroaromatic ring.

[0022] The present application also provides an organic electroluminescent device comprising a cathode, an anode and one or more organic layers between the two electrodes, at least one of the organic layers being an emitting layer, and the emitting layer comprising at least one or more of the boron-nitrogen compounds according to the present application.

[0023] Advantages

[0024] The boron-nitrogen compound of the present application has high color purity and high reverse intersystem crossing rate. The introduction of rigid groups on the central benzene ring increases the rigidity of the molecule, reduces the molecular vibration relaxation, is conducive to reducing the FWHM of the molecule, and further improves the color purity of the molecule; the introduction of heteroatom-containing phenoxazine or phenothiazine derivative donors at the same time promotes the spin-orbit coupling to improve the reverse intersystem crossing rate of the triplet state to the singlet state exciton, and weakens the three-line state exciton smoke extinction process. In addition, the introduction of bulky peripheral substituents suppresses the aggregation between molecules, weakens the mutual quenching phenomenon between molecules, and improves the luminous efficiency. Thus, when it is applied to an organic electroluminescent device, the color purity and luminous efficiency of the organic electroluminescent device can be improved, which plays an important role in further popularizing the organic electroluminescent technology. DETAILED DESCRIPTION

[0025] The technical solutions of the embodiments of the present application will be described clearly and completely below. Obviously, the described embodiments are only part of the embodiments of the present application, rather than all the embodiments. After reading the present application, those skilled in the art can make various modifications to the equivalent forms of the present application, which fall within the scope defined by the present application.

[0026] In the compounds of the present application, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes atoms in both their natural isotopic abundance and non-natural abundance.

[0027] In the specification, “*-” means a moiety connected to another substituent. “*-” can be connected to any optional position of the connected group / fragment. For example represents and so on.

[0028] In the specification, when the position of a substituent on a ring is not fixed, it means that it can be connected to any one of the corresponding optional positions of the ring. For example, may represent and so on.

[0029] Examples of the halogen atom described in the present application can include fluorine, chlorine, bromine, and iodine.

[0030] The alkyl group described in the present application refers to a monovalent group obtained by removing one hydrogen atom from an alkane molecule, which can be a straight-chain alkyl group or a branched-chain alkyl group, preferably has 1 to 30 carbon atoms, more preferably has 1 to 12 carbon atoms, particularly preferably has 1 to 8 carbon atoms, and most preferably has 1 to 6 carbon atoms. Examples can include methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, and the like, but are not limited thereto.

[0031] The cycloalkyl group according to the present application refers to a monovalent group obtained by removing one hydrogen atom from a cyclic alkane molecule, preferably having 3 to 12 carbon atoms, more preferably having 3 to 10 carbon atoms, and particularly preferably having 3 to 6 carbon atoms. Examples can include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, and the like, but are not limited thereto.

[0032] The aryl group according to the present application refers to a monovalent group obtained by removing one hydrogen atom from an aromatic carbon of an aromatic hydrocarbon molecule, which can be a monocyclic aryl group, a polycyclic aryl group, or a fused ring aryl group, preferably having 6 to 60 carbon atoms, more preferably 6 to 30 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Examples can include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, triphenylenyl, perylenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, benzofluorenyl, and the like, but are not limited thereto.

[0033] The heteroaryl group according to the present application refers to a monovalent group obtained by replacing one or more aromatic carbon atoms in an aromatic hydrocarbon molecule with a heteroatom, which includes but is not limited to oxygen, sulfur, nitrogen, silicon, or phosphorus atoms, preferably having 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, and most preferably 2 to 12 carbon atoms. Examples can include pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiophenyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, bipyridyl, bipyrimidyl, phenylpyridyl, phenylpyrimidyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinazolyl, quinoxalyl, benzoquinazolyl, benzoquinoxalyl, phenanthrolinyl, naphthylidinyl, indolyl, benzothiophenyl, benzofuranyl, N-heterobenzothiophenyl, N-heterobenzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, N-heterodibenzofuranyl, benzo-dibenzofuranyl, dibenzothiophenyl, N-heterodibenzothiophenyl, benzo-dibenzothiophenyl, dibenzoxazolyl, dibenzimidazolyl, dibenzothiazolyl, carbazolyl, N-heterocarbazolyl, benzocarbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiinyl, spirofluorenoxanthrene, spirofluorenothioxanthrene, and the like, but are not limited thereto.

[0034] The alicyclic group according to the present application refers to a cyclic hydrocarbon having aliphatic properties, containing closed carbon rings in the molecule, preferably having 3 to 60 carbon atoms, more preferably 3 to 30 carbon atoms, further preferably 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, most preferably 3 to 7 carbon atoms. It can form a single ring hydrocarbon or a polycyclic hydrocarbon, and can be completely unsaturated or partially unsaturated, such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, cycloheptene, etc., but is not limited thereto. Multiple single ring hydrocarbons can also be connected in various ways: two rings in the molecule can share a carbon atom to form a spiro ring; two carbon atoms on the ring can be connected by a carbon bridge to form a bridged ring; several rings can also be connected to each other to form a cage structure.

[0035] The silyl group according to the present application means a -SiH3 group, and the "substituted or unsubstituted silyl group" means that one or more H of the silyl group is substituted with a substituent or is not substituted. The "substituted or unsubstituted silyl group" can be represented by -Si(Rk)3, wherein each Rk is the same or different and is selected from the group consisting of hydrogen, deuterium, tritium, a cyano group, a halogen, a nitro group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkenyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic fused ring group, and a substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic fused ring group. Preferably, each Rk is the same or different and is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, and a substituted or unsubstituted C6-C60 aryl group. The number of carbon atoms of the alkyl group is preferably 1 to 20, preferably 1 to 15, more preferably 1 to 10, and most preferably 1 to 8. The number of carbon atoms of the cycloalkyl group is preferably 3 to 20, preferably 3 to 15, more preferably 3 to 10, and most preferably 3 to 7. The number of carbon atoms of the aryl group is preferably 6 to 20, preferably 6 to 13, more preferably 6 to 12, and most preferably 6 to 10. Preferably, each Rk is the same or different and is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted pentyl group, a substituted or unsubstituted hexyl group, a substituted or unsubstituted heptyl group, a substituted or unsubstituted octyl group, a substituted or unsubstituted cyclopropyl group, a substituted or unsubstituted cyclobutyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted cycloheptyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted norbornyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinolyl group, and a substituted or unsubstituted isoquinolyl group. Preferably, the substituted silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group, a tri-t-butylsilyl group, a t-butyldimethylsilyl group, a vinyl dimethylsilyl group, an isopropyl dimethylsilyl group, a triphenylsilyl group, a diphenylmethylsilyl group, a phenyldimethylsilyl group, a diphenylpyridylsilyl group, a phenyl dipyridylsilyl group, a tripyridylsilyl group, and the like, but is not limited thereto. The substituted silyl group is preferably a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group, a tri-t-butylsilyl group, a t-butyldimethylsilyl group, a vinyl dimethylsilyl group, an isopropyl dimethylsilyl group, a triphenylsilyl group, a diphenylmethylsilyl group, a phenyldimethylsilyl group.

[0036] The arylene group, heteroarylene group, fused ring group according to the present application means a divalent group having two bonding sites on an aryl group. They can be applied to the above-mentioned aryl group, heteroaryl group, fused ring group except that they are divalent groups.

[0037] The "substituted" according to the present application such as "substituted silyl group, substituted alkyl group, substituted cycloalkyl group, substituted aryl group, substituted heteroaryl group, substituted arylene group, substituted heteroarylene group, substituted fused ring group" means independently mono- or poly-substituted with hydrogen, deuterium, cyano group, halogen, nitro group, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C2-C60 heteroaryl group, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aryl fused ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl fused ring group, and the like, but not limited thereto, and when two or more substituents exist, two adjacent substituents can be linked to form a ring. Preferably, mono- or poly-substituted with deuterium, fluorine, chlorine, bromine, iodine, cyano group, nitro group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, tert-butyl group, deuterated tert-butyl group, cyclopentyl group, cyclohexyl group, adamantyl group, norbornyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, deuterated phenyl group, deuterated biphenyl group, deuterated terphenyl group, deuterated naphthyl group, anthracenyl group, phenanthrenyl group, triphenylenyl group, perylenyl group, pyrenyl group, benzyl group, tert-butyl-substituted phenyl group, adamantyl-substituted phenyl group, 9,9-dimethylfluorenyl group, 9-methyl-9-phenylfluorenyl group, 9,9'-spirobifluorenyl group, 9,9-diphenylfluorenyl group, diphenylamino group, pyridyl group, pyrimidinyl group, triazinyl group, carbazolyl group, furanyl group, thienyl group, benzofuranyl group, benzothienyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, dibenzofuranyl group, dibenzothienyl group, phenothiazinyl group, phenoxazinyl group, and the like, but not limited thereto.

[0038] The "linked to form a ring" according to the present application means that two groups are linked to each other by a chemical bond and optionally aromatized. The following is an example:

[0039]

[0040] In the present application, the ring formed by linking can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of both, and the ring formed by linking can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a spiro ring, or a fused ring, for example, benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenyl, cyclohexene, cyclohexane, cyclohexanophenyl, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but not limited thereto.

[0041] The present application provides a boron-nitrogen compound selected from a structure represented by Formula 1:

[0042]

[0043] The X1, X2 are the same or different and selected from one of a single bond, O, S, Se, N(R a ), C(R b R b '), Si(R b R b '), Ge(R b R b '), and at least one of X1, X2 is not selected from a single bond;

[0044] The R a is selected from any one of a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C6-C60 aromatic ring, and a substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C2-C60 heteroaromatic ring;

[0045] The R b , R b ' are the same or different and selected from any one of hydrogen, deuterium, a cyano group, a halogen, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C6-C60 aromatic ring, and a substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C2-C60 heteroaromatic ring; or R b , R b ' can be bonded to form a substituted or unsubstituted ring;

[0046] The w is the same or different and selected from a C(R1) or N atom;

[0047] R1is selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted amino group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C2-C60 heteroaryl group, substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C6-C60 aromatic ring, substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C2-C60 heteroaromatic ring; or adjacent two R1may be bonded to form a substituted or unsubstituted ring;

[0048] R0is selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C2-C60 heteroaryl group, substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C6-C60 aromatic ring, substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C2-C60 heteroaromatic ring;

[0049] Ar1is selected from the structure represented by formula a-1;

[0050] X3is selected from one of single bond, O, S, Se, N(R c ), C(R d R d ’), Si(R d R d ’), Ge(R d R d ’);

[0051] R c is selected from any one of substituted or unsubstituted silyl group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C2-C60 heteroaryl group, substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C6-C60 aromatic ring, substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C2-C60 heteroaromatic ring;

[0052] R d , R dany one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C2-C60 heteroaryl group, substituted or unsubstituted condensed ring group of C3-C30 alicyclic ring and C6-C60 aromatic ring, substituted or unsubstituted condensed ring group of C3-C30 alicyclic ring and C2-C60 heteroaromatic ring, which are the same or different; or R d , R d may be bonded to form a substituted or unsubstituted ring;

[0053] the v is selected from a C(R2) or N atom, which are the same or different;

[0054] the R2 is selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C2-C60 heteroaryl group, substituted or unsubstituted condensed ring group of C3-C30 alicyclic ring and C6-C60 aromatic ring, substituted or unsubstituted condensed ring group of C3-C30 alicyclic ring and C2-C60 heteroaromatic ring;

[0055] the R3 is selected from any one of substituted or unsubstituted silyl group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C2-C60 heteroaryl group, substituted or unsubstituted condensed ring group of C3-C30 alicyclic ring and C6-C60 aromatic ring, substituted or unsubstituted condensed ring group of C3-C30 alicyclic ring and C2-C60 heteroaromatic ring, or the corresponding N atom of R3 is a site bonded to L1;

[0056] the Ar2 is selected from any one of cyano, halogen, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C2-C60 heteroaryl group, substituted or unsubstituted condensed ring group of C3-C30 alicyclic ring and C6-C60 aromatic ring, substituted or unsubstituted condensed ring group of C3-C30 alicyclic ring and C2-C60 heteroaromatic ring;

[0057] The L1 and L2 are the same or different and are selected from one of the following: single bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C2-C60 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings in a fused cycloalcoholic group, or substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroarylene rings in a fused cycloalcoholic group.

[0058] Preferably, the compound is selected from any one of Formulas 1-1 to 1-4:

[0059]

[0060] The X4 and X5 that are the same or different are selected from O, S, Se, N(R). a ), C(R b R b '), Si C(R) b R b '), Ge C(R) b R b One of the following;

[0061] The w atoms, whether identical or different, are selected from C(R1) or N atoms;

[0062] The same or different v are selected from C(R2) or N atoms;

[0063] The R0, L1, L2, Ar2, R a R b The definitions of X3 and R3 are the same as those in Equation 1.

[0064] Preferably, the boron-nitrogen compound has at most four w atoms selected from N atoms; more preferably, the boron-nitrogen compound has at most three w atoms selected from N atoms; even more preferably, the boron-nitrogen compound has at most two w atoms selected from N atoms; more preferably, the boron-nitrogen compound has at most one w atom selected from N atoms. Preferably, each six-membered ring has at most one w atom selected from N atoms.

[0065] Preferred, R aany one of hydrogen, deuterium, cyano, nitro, a halogen atom, a hydroxyl group, a trifluoromethyl group, a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, an i-butyl group, a s-butyl group, a t-butyl group, a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a norbornane group, an adamantane group, a phenyl group, a biphenyl group, a terphenyl group, a benzocyclopropane group, a benzocyclobutane group, a benzocyclopentane group, a benzocyclohexane group, a benzocycloheptane group, a naphthyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a quinolyl group, an isoquinolyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated n-propyl group, a deuterated i-propyl group, a deuterated n-butyl group, a deuterated i-butyl group, a deuterated s-butyl group, a deuterated t-butyl group, a deuterated adamantane group, a deuterated norbornane group, a deuterated phenyl group, a deuterated biphenyl group, a deuterated terphenyl group, a deuterated naphthyl group, a deuterated pyridyl group, a deuterated pyrimidinyl group, a deuterated pyrazinyl group, a deuterated pyridazinyl group, a deuterated quinolyl group, a deuterated isoquinolyl group, a methyl-substituted phenyl group, a methyl-substituted biphenyl group, a methyl-substituted naphthyl group, an ethyl-substituted phenyl group, an ethyl-substituted biphenyl group, an i-propyl-substituted phenyl group, an i-propyl-substituted biphenyl group, a t-butyl-substituted phenyl group, a t-butyl-substituted biphenyl group, a t-butyl-substituted naphthyl group.

[0066] Preferably, the R b any one of hydrogen, deuterium, cyano, nitro, a halogen atom, a hydroxyl group, a trifluoromethyl group, a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, an i-butyl group, a s-butyl group, a t-butyl group, a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a norbornane group, an adamantane group, a phenyl group, a biphenyl group, a terphenyl group, a benzocyclopropane group, a benzocyclobutane group, a benzocyclopentane group, a benzocyclohexane group, a benzocycloheptane group, a naphthyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a quinolyl group, an isoquinolyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated n-propyl group, a deuterated i-propyl group, a deuterated n-butyl group, a deuterated i-butyl group, a deuterated s-butyl group, a deuterated t-butyl group, a deuterated adamantane group, a deuterated norbornane group, a deuterated phenyl group, a deuterated biphenyl group, a deuterated terphenyl group, a deuterated naphthyl group, a deuterated pyridyl group, a deuterated pyrimidinyl group, a deuterated pyrazinyl group, a deuterated pyridazinyl group, a deuterated quinolyl group, a deuterated isoquinolyl group, a methyl-substituted phenyl group, a methyl-substituted biphenyl group, a methyl-substituted naphthyl group, an ethyl-substituted phenyl group, an ethyl-substituted biphenyl group, an i-propyl-substituted phenyl group, an i-propyl-substituted biphenyl group, a t-butyl-substituted phenyl group, a t-butyl-substituted biphenyl group, a t-butyl-substituted naphthyl group. b , R b forms a spiro ring.

[0067] Preferably, R1and R2are the same or different and are selected from the group consisting of hydrogen, deuterium, cyano, halogen atom, nitro group, amino group, trimethylsilyl group, triethylsilyl group, tri-t-butylsilyl group, t-butyl dimethylsilyl group, triphenylsilyl group, diphenylmethylsilyl group, phenyl dimethylsilyl group, methyl group, trifluoromethyl group, ethyl group, isopropyl group, t-butyl group, deuterated t-butyl group, cyclopentyl group, cyclohexyl group, benzcyclopentane group, benzcyclohexane group, adamantyl group, norbornane group, phenyl group, biphenyl group, terphenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, triphenylene group, perylenyl group, 9,9-dimethylfluorenyl group, 9-methyl-9-phenylfluorenyl group, 9,9'-spirobifluorenyl group, 9,9-diphenylfluorenyl group, pyridyl group, pyrimidyl group, pyrazinyl group, pyridazinyl group, triazinyl group, furanyl group, thienyl group, pyrrolyl group, oxazolyl group, thiazolyl group, imidazolyl group, quinolyl group, isoquinolyl group, quinazolyl group, quinoxalyl group, phenanthrolinyl group, naphthrydinyl group, indolyl group, benzothienyl group, benzofuranyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, dibenzofuranyl group, N-hetero-dibenzofuranyl group, benzo-dibenzofuranyl group, dibenzothienyl group, N-hetero-dibenzothienyl group, benzo-dibenzothienyl group, carbazolyl group, N-hetero-carbazolyl group, benzo-carbazolyl group, indolyl group, fluorine-substituted phenyl group, fluorine-substituted biphenyl group, cyano-substituted phenyl group, cyano-substituted biphenyl group, silyl-substituted phenyl group, silyl-substituted biphenyl group, methyl-substituted phenyl group, methyl-substituted biphenyl group, ethyl-substituted phenyl group, ethyl-substituted biphenyl group, isopropyl-substituted phenyl group, isopropyl-substituted biphenyl group, t-butyl-substituted phenyl group, t-butyl-substituted biphenyl group, trifluoromethyl-substituted phenyl group, trifluoromethyl-substituted biphenyl group, adamantyl-substituted phenyl group, adamantyl-substituted biphenyl group, norbornane-substituted phenyl group, norbornane-substituted biphenyl group, deuterated dibenzofuranyl group, deuterated dibenzothienyl group, deuterated methyl-substituted phenyl group, deuterated methyl-substituted biphenyl group, deuterated t-butyl-substituted phenyl group, deuterated t-butyl-substituted biphenyl group, deuterated phenyl group, deuterated biphenyl group, deuterated terphenyl group, deuterated naphthyl group, and the like; or two adjacent R1may be bonded to form a substituted or unsubstituted benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, furan ring, thiophene ring, benzofuran ring, benzothiophene ring; or two adjacent R2may be bonded to form a substituted or unsubstituted benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, furan ring, thiophene ring, benzofuran ring, benzothiophene ring.

[0068] Preferably, R0is selected from any one of hydrogen, deuterium, phenyl, biphenyl, terphenyl, fluorosubstituted phenyl, fluorosubstituted biphenyl, silyl-substituted phenyl, silyl-substituted biphenyl, cyano-substituted phenyl, cyano-substituted biphenyl, methyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, t-butyl-substituted phenyl, t-butyl-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, dibenzofuranyl, dibenzothiophenyl, deuterated methyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated t-butyl-substituted phenyl, deuterated t-butyl-substituted biphenyl, deuterated phenyl, deuterated biphenyl, phenothiazinyl, phenoxazinyl, carbazolyl.

[0069] Preferably, the compound is selected from any one of the following formulae 2-1 to 2-10:

[0070]

[0071] Preferably, at most 3 v in formula a-1 are selected from N atoms; further preferably, at most 2 v in formula a-1 are selected from N atoms; still further preferably, at most 1 v in formula a-1 is selected from N atoms. Preferably, at most 1 v in each six-membered ring is selected from N atoms.

[0072] Still further preferably, formula a-1 is selected from any one of the following groups:

[0073]

[0074]

[0075] Preferably, R xany one of hydrogen, deuterium, cyano, halogen atom, nitro group, amino group, trimethylsilyl group, triethylsilyl group, tri-t-butylsilyl group, t-butyl dimethylsilyl group, triphenylsilyl group, diphenylmethylsilyl group, phenyldimethylsilyl group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, t-butyl group, deuterated t-butyl group, cyclopentyl group, cyclohexyl group, benzcyclopentane group, benzcyclohexane group, adamantyl group, norbornane group, phenyl group, biphenyl group, terphenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, triphenylene group, perylenyl group, 9,9-dimethylfluorenyl group, 9-methyl-9-phenylfluorenyl group, 9,9-spiro-bifluorenyl group, 9,9-diphenylfluorenyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, furanyl group, thienyl group, pyrrolyl group, oxazolyl group, thiazolyl group, imidazolyl group, quinolyl group, isoquinolyl group, quinazolyl group, quinoxalyl group, phenanthrolinyl group, naphthrydinyl group, indolyl group, benzothiophenyl group, benzofuranyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, dibenzofuranyl group, N-hetero-dibenzofuranyl group, benzo-dibenzofuranyl group, dibenzothiophenyl group, N-hetero-dibenzothiophenyl group, benzo-dibenzothiophenyl group, carbazolyl group, N-hetero-carbazolyl group, benzo-carbazolyl group, indolyl group, fluorine-substituted phenyl group, fluorine-substituted biphenyl group, cyano-substituted phenyl group, cyano-substituted biphenyl group, silyl-substituted phenyl group, silyl-substituted biphenyl group, methyl-substituted phenyl group, methyl-substituted biphenyl group, ethyl-substituted phenyl group, ethyl-substituted biphenyl group, isopropyl-substituted phenyl group, isopropyl-substituted biphenyl group, t-butyl-substituted phenyl group, t-butyl-substituted biphenyl group, trifluoromethyl-substituted phenyl group, trifluoromethyl-substituted biphenyl group, adamantyl-substituted phenyl group, adamantyl-substituted biphenyl group, norbornane-substituted phenyl group, norbornane-substituted biphenyl group, deuterated dibenzofuranyl group, deuterated dibenzothiophenyl group, deuterated methyl-substituted phenyl group, deuterated methyl-substituted biphenyl group, deuterated t-butyl-substituted phenyl group, deuterated t-butyl-substituted biphenyl group, deuterated phenyl group, deuterated biphenyl group, deuterated terphenyl group, deuterated naphthyl group; x any one of hydrogen, deuterium, cyano, halogen atom, nitro group, amino group, trimethylsilyl group, triethylsilyl group, tri-t-butylsilyl group, t-butyl dimethylsilyl group, triphenylsilyl group, diphenylmethylsilyl group, phenyldimethylsilyl group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, t-butyl group, deuterated t-butyl group, cyclopentyl group, cyclohexyl group, benzcyclopentane group, benzcyclohexane group, adamantyl group, norbornane group, phenyl group, biphenyl group, terphenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, triphenylene group, perylenyl group, 9,9-dimethylfluorenyl group, 9-methyl-9-phenylfluorenyl group, 9,9-spiro-bifluorenyl group, 9,9-diphenylfluorenyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, furanyl group, thienyl group, pyrrolyl group, oxazolyl group, thiazolyl group, imidazolyl group, quinolyl group, isoquinolyl group, quinazolyl group, quinoxalyl group, phenanthrolinyl group, naphthrydinyl group, indolyl group, benzothiophenyl group, benzofuranyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, dibenzofuranyl group, N-hetero-dibenzofuranyl group, benzo-dibenzofuranyl group, dibenzothiophenyl group, N-hetero-dibenzothiophenyl group, benzo-dibenzothiophenyl group, carbazolyl group, N-hetero-carbazolyl group, benzo-carbazolyl group, indolyl group, fluorine-substituted phenyl group, fluorine-substituted biphenyl group, cyano-substituted phenyl group, cyano-substituted biphenyl group, silyl-substituted phenyl group, silyl-substituted biphenyl group, methyl-substituted phenyl group, methyl-substituted biphenyl group, ethyl-substituted phenyl group, ethyl-substituted biphenyl group, isopropyl-substituted phenyl group, isopropyl-substituted biphenyl group, t-butyl-substituted phenyl group, t-butyl-substituted biphenyl group, trifluoromethyl-substituted phenyl group, trifluoromethyl-substituted biphenyl group, adamantyl-substituted phenyl group, adamantyl-substituted biphenyl group, norbornane-substituted phenyl group, norbornane-substituted biphenyl group, deuterated dibenzofuranyl group, deuterated dibenzothiophenyl group, deuterated methyl-substituted phenyl group, deuterated methyl-substituted biphenyl group, deuterated t-butyl-substituted phenyl group, deuterated t-butyl-substituted biphenyl group, deuterated phenyl group, deuterated biphenyl group, deuterated terphenyl group, deuterated naphthyl group;

[0076] R3is the same or different selected from any one of methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornane, adamantane, phenyl, biphenyl, terphenyl, benzcyclopropane, benzcyclobutane, benzcyclopentane, benzcyclohexane, benzcycloheptane, naphthyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated i-propyl, deuterated n-butyl, deuterated i-butyl, deuterated s-butyl, deuterated t-butyl, deuterated adamantane, deuterated norbornane, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated pyridyl, deuterated pyrimidyl, deuterated pyrazinyl, deuterated pyridazinyl, deuterated quinolinyl, deuterated isoquinolinyl, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, i-propyl-substituted phenyl, i-propyl-substituted biphenyl, t-butyl-substituted phenyl, t-butyl-substituted biphenyl, t-butyl-substituted naphthyl, 9,9-dimethylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9-spiro-bifluorenyl, 9,9-diphenylfluorenyl.

[0077] said n1is the same or different selected from 0, 1, 2, 3 or 4, said n2is selected from 0, 1, 2 or 3, and said n3is selected from 0, 1 or 2.

[0078] Preferably, Ar2is selected from cyano, halogen, nitro, trimethylsilyl, triethylsilyl, tri-t-butylsilyl, t-butyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, methyl, trifluoromethyl, deuterated methyl, ethyl, i-propyl, t-butyl, deuterated t-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, or is selected from any one of the following formulae a-1 to a-12:

[0079]

[0080] said z is the same or different selected from C(R n ) or N atom;

[0081] Preferably, R nThe same or different are selected from hydrogen, deuterium, cyano, halogen atom, nitro, amino, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, cyclohexyl, benzocyclopentyl, benzocyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyrene. Triphenylene, Perylene, 9,9-Dimethylfluorenyl, 9-Methyl-9-phenylfluorenyl, 9,9-Spirodifluorenyl, 9,9-Diphenylfluorenyl, Pyridyl, Pyrazinyl, Pyridazinyl, Triazinyl, Furanyl, Thiopheneyl, Pyrroleyl, Oxazolyl, Thiazolyl, Imidazolyl, Quinolinyl, Isoquinolinyl, Quinazolinyl, Quinoxalinyl, o-Phenanthrolinel, Naphthidyl, Indolyl, Benzothiophene, Benzofuranyl, Benzooxazolyl, Benzoimidazolyl, Benzothiazolyl, Dibenzofuranyl, N-hexadibenzofuranyl Benzodibenzofuranyl, dibenzothiophenyl, N-hexabenzothiophenyl, benzodibenzothiophenyl, carbazoleyl, N-hexacarbazoleyl, benzocarbazoleyl, indolyl, fluorinated phenyl, fluorinated biphenyl, cyano-substituted phenyl, cyano-substituted biphenyl, silyl-substituted phenyl, silyl-substituted biphenyl, methyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, tert-butyl-substituted phenyl, tert-butyl-substituted phenyl Any one of the following: butyl-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuterated dibenzofuranyl, deuterated dibenzothiopheneyl, deuterated methyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated tert-butyl-substituted phenyl, deuterated tert-butyl-substituted biphenyl, deuterated phenyl, deuterated biphenyl, deuterated tert-phenyl, deuterated naphthyl; or two adjacent R groups. n They can bond with each other to form substituted or unsubstituted rings: benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, furan ring, thiophene ring, benzofuran ring, and benzothiophene ring.

[0082] Preferably, the ring H is selected from cyclopropyl, butyl, pentyl, cyclohexyl, and cycloheptyl.

[0083] The X8 and X9 that are the same or different are selected from O, S, C(R). e R e '), N(R f One of them;

[0084] Preferred, R e R eany one of hydrogen, deuterium, cyano, nitro, a halogen atom, a hydroxyl group, a trifluoromethyl group, a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, an i-butyl group, a sec-butyl group, a t-butyl group, a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a norbornane group, an adamantane group, a phenyl group, a biphenyl group, a terphenyl group, a benzcyclopropane group, a benzcyclobutane group, a benzcyclopentane group, a benzcyclohexane group, a benzcycloheptane group, a naphthyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a quinolyl group, an isoquinolyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated n-propyl group, a deuterated i-propyl group, a deuterated n-butyl group, a deuterated i-butyl group, a deuterated sec-butyl group, a deuterated t-butyl group, a deuterated adamantane group, a deuterated norbornane group, a deuterated phenyl group, a deuterated biphenyl group, a deuterated terphenyl group, a deuterated naphthyl group, a deuterated pyridyl group, a deuterated pyrimidinyl group, a deuterated pyrazinyl group, a deuterated pyridazinyl group, a deuterated quinolyl group, a deuterated isoquinolyl group, a methyl-substituted phenyl group, a methyl-substituted biphenyl group, a methyl-substituted naphthyl group, an ethyl-substituted phenyl group, an ethyl-substituted biphenyl group, an i-propyl-substituted phenyl group, an i-propyl-substituted biphenyl group, a t-butyl-substituted phenyl group, a t-butyl-substituted biphenyl group, a t-butyl-substituted naphthyl group; or R e , R e form a substituted or unsubstituted: spiro-pentane ring, spiro-hexane ring, spiro-heptane ring, spiro-fluorene ring.

[0085] Preferably, each of the R f any one of hydrogen, deuterium, cyano, nitro, a halogen atom, a hydroxyl group, a trifluoromethyl group, a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, an i-butyl group, a sec-butyl group, a t-butyl group, a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a norbornane group, an adamantane group, a phenyl group, a biphenyl group, a terphenyl group, a benzcyclopropane group, a benzcyclobutane group, a benzcyclopentane group, a benzcyclohexane group, a benzcycloheptane group, a naphthyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a quinolyl group, an isoquinolyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated n-propyl group, a deuterated i-propyl group, a deuterated n-butyl group, a deuterated i-butyl group, a deuterated sec-butyl group, a deuterated t-butyl group, a deuterated adamantane group, a deuterated norbornane group, a deuterated phenyl group, a deuterated biphenyl group, a deuterated terphenyl group, a deuterated naphthyl group, a deuterated pyridyl group, a deuterated pyrimidinyl group, a deuterated pyrazinyl group, a deuterated pyridazinyl group, a deuterated quinolyl group, a deuterated isoquinolyl group, a methyl-substituted phenyl group, a methyl-substituted biphenyl group, a methyl-substituted naphthyl group, an ethyl-substituted phenyl group, an ethyl-substituted biphenyl group, an i-propyl-substituted phenyl group, an i-propyl-substituted biphenyl group, a t-butyl-substituted phenyl group, a t-butyl-substituted biphenyl group, a t-butyl-substituted naphthyl group.

[0086] Preferably, in each of the formulae a-1 to a-12, at most 3 of the z are selected from N atoms; further preferably, in each of the formulae a-1 to a-12, at most 2 of the z are selected from N atoms; still further preferably, in each of the formulae a-1 to a-12, at most 1 of the z is selected from N atoms.

[0087] Preferably, L1, L2is selected from a single bond, or any one of the following groups:

[0088]

[0089] Preferably, R m the same or different, is selected from hydrogen, deuterium, cyano, a halogen atom, a nitro group, an amino group, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, cyclohexyl, benzcyclopentane, benzcyclohexane, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, triphenylenyl, perylenyl, 9,9-dimethylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9-spiro-bifluorenyl, 9,9-diphenylfluorenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, phenanthrolinyl, naphthrydinyl, indolyl, benzothiophenyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, N-hetero-dibenzofuranyl, benzo-dibenzofuranyl, dibenzothiophenyl, N-hetero-dibenzothiophenyl, benzo-dibenzothiophenyl, carbazolyl, N-hetero-carbazolyl, benzo-carbazolyl, indolyl, fluorine-substituted phenyl, fluorine-substituted biphenyl, cyano-substituted phenyl, cyano-substituted biphenyl, silyl-substituted phenyl, silyl-substituted biphenyl, methyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuterated dibenzofuranyl, deuterated dibenzothiophenyl, deuterated methyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated tert-butyl-substituted phenyl, deuterated tert-butyl-substituted biphenyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl; or two adjacent R m may be bonded to form a substituted or unsubstituted benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, furan ring, thiophene ring, benzofuran ring, benzothiophene ring.

[0090] q1 is selected from 0, 1, 2, 3, or 4, q2 is selected from 0, 1, 2, or 3, q3 is selected from 0, 1, or 2, q4 is selected from 0, 1, 2, 3, 4, 5, or 6, q5 is selected from 0, 1, 2, 3, 4, or 5, q6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, q7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and q8 is selected from 0, 1, 2, 3, 4, 5, 6, or 7.

[0091] Most preferably, the boron-nitrogen compound is selected from any one of the following structures:

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117] The above lists some specific structural forms of the compound of formula 1 according to the present application, but the present application is not limited to the listed chemical structures, and any structure based on the structure shown in formula 1 and having substituents as defined above should be included.

[0118] Meanwhile, the present application also provides a preparation method of the compound of formula 1, and the specific synthesis route is shown below, but is not limited thereto:

[0119]

[0120] The sources of the above raw material h, raw material a, raw material aa, raw material c, raw material d and raw material e are not particularly limited, and can be commercial products or prepared by using common methods in the art.

[0121] The definitions of R0, X1, X2, L1, L2, Ar1 and Ar2 are the same as those in formula I above, and Xa, Xb, Xc and Xd are independently selected from any one of H, F, Cl, Br and I;

[0122] The main reaction types involved in the present application are Suzuki coupling reaction and Buchwald-Hartwig coupling reaction. The amount of each substance is the amount used in one coupling reaction.

[0123] In addition, the present application also provides an organic electroluminescent device, which comprises an organic layer, and the organic layer comprises at least one or more than one of the boron-nitrogen compounds according to the present application.

[0124] Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one or more than one of the boron-nitrogen compounds according to the present application.

[0125] Preferably, the light-emitting layer comprises a host material and a dopant material, and the dopant material comprises at least one or more than one of the boron-nitrogen compounds according to the present application.

[0126] Specifically, the organic layer includes an emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, an emitting auxiliary layer, etc., but is not limited thereto.

[0127] As the anode of the present application, a transmissive electrode, a reflective electrode or a semi-transmissive electrode can be selected, and when the anode is a transmissive electrode, the anode material can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO) or any combination thereof; when the anode is a semi-transmissive electrode or a reflective electrode, the anode material can be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) or any combination thereof.

[0128] As the hole injection layer of the present application, a material having good hole accepting ability is preferred. Specific examples include metal porphyrin, oligothiophene, arylamine, hexacarbonitrile hexaazatriphenylene, quinacridone, perylene material, etc., but are not limited thereto.

[0129] As the hole transport layer of the present application, a material having high hole mobility is preferred. Specific examples can include diphenylamine compounds, fluorene compounds and carbazole compounds, biphenyldiamine compounds and other materials, but are not limited thereto.

[0130] As the emitting layer material of the present application, red, green or blue emitting materials can be used, which generally contain guest (doped) materials and host materials, the guest materials can be simple fluorescent materials or phosphorescent materials, or combinations of fluorescent and phosphorescent materials. The host materials of the emitting layer not only need to have bipolar charge transport properties, but also need to have appropriate energy levels to effectively transfer excitation energy to the guest emitting materials, and such materials can be diphenylstyryl aryl derivatives, stilbene derivatives, carbazole derivatives, triarylamine derivatives, anthracene derivatives and pyrene derivatives, etc. The guest materials can be selected from any one or several of the following structures: metal complexes (such as iridium complexes, platinum complexes, osmium complexes, rhodium complexes, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives, etc., but are not limited thereto. The guest material is preferably the boron-nitrogen compound of formula 1 of the present application.

[0131] As the electron transport layer material of the present application, a material having high electron mobility is preferred. Specific examples can include quinoline, imidazole, phenanthroline, triazole, metal chelate, azabenzene derivative, diazanthracene derivative, silicon-containing heterocyclic compound, boron-containing heterocyclic compound, cyano, benzimidazole, etc., but are not limited thereto.

[0132] As the electron injection layer material of the present application, a material having a low work function is preferred. Specific examples can include: metals, alkali metals, alkaline earth metals, halides of alkali metals, halides of alkaline earth metals, oxides of alkali metals, oxides of alkaline earth metals, alkali metal salts, alkaline earth metal salts, metal complexes, etc. Examples can include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, cesium 8-hydroxyquinoline, tris(8-hydroxyquinoline)aluminum, etc., but are not limited thereto.

[0133] As the cathode of the present application, a transmissive electrode, a semi-reflective electrode, or a reflective electrode can be selected. When the cathode is a transmissive electrode, the cathode material can be selected from transparent metal oxides (e.g., ITO, IZO, etc.); when the cathode is a semi-reflective electrode or a reflective electrode, the cathode material can be selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds including the same, or mixtures thereof (e.g., a mixture of Ag and Mg), but is not limited thereto.

[0134] The organic layer of the organic electroluminescent device described above can be deposited by a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, etc. When a vacuum deposition method is used, the conditions of vacuum deposition are changed depending on the compound.

[0135] The manufacture of the organic electroluminescent device described above is specifically explained in the following examples. However, the following examples are only for exemplifying the present specification, and the scope of the present specification is not limited to the examples.

[0136] Preparation and characterization of compounds

[0137] Explanation of raw materials, reagents, and characterization equipment:

[0138] The present application does not have a particular limitation on the source of raw materials used in the following examples, and can be a commercially available product or prepared by a preparation method well known to those skilled in the art.

[0139] Mass spectrometry uses a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer in the United Kingdom, with chloroform as the solvent;

[0140] Elemental analysis uses a Vario EL cube organic elemental analyzer of Elementar Company in Germany, and the sample mass is 5-10 mg.

[0141] Synthesis Example 1: Preparation of compound 5

[0142]

[0143] Preparation of intermediate A-5:

[0144] Compound h-5 (31.65 g, 150 mmol), compound a-5 (21.95 g, 180 mmol) and potassium carbonate (37.32 g, 270 mmol) were dissolved in a mixed solution of THF and water (675 mL, volume ratio 4:1), and Pd(PPh3)4(5.20 g, 4.5 mmol) was added under nitrogen and stirred at reflux for 12 hours. After the reaction was completed, the mixture was washed with dichloromethane and water, and the organic phase was concentrated and purified by column chromatography (eluent: petroleum ether) to obtain intermediate A-5 (29.85 g, yield 95.58%), which had a solid purity of ≧99.88% as determined by HPLC. Mass spectrum m / z: 208.0489 (theoretical value: 208.0500).

[0145] Preparation of intermediate B-5:

[0146] Compound A-5 (20.82 g, 100 mmol) was dissolved in 335 mL of tetrahydrofuran, and lithium diisopropylamide (LDA, 50 mL, 100 mmol, 2M tetrahydrofuran solution) was added dropwise under nitrogen at -20°C, and stirring was continued for 1 hour. Then, iodine (25.38 g, 100 mmol) was added, and the temperature was returned to room temperature, and stirring was continued for 4 hours. After the reaction was completed, the mixture was washed with a sodium thiosulfate solution and dichloromethane, and the organic phase was concentrated and purified by column chromatography (eluent: petroleum ether) to obtain intermediate B-5 (29.23 g, yield 87.50%), which had a solid purity of ≧99.81% as determined by HPLC. Mass spectrum m / z: 333.9454 (theoretical value: 333.9466).

[0147] Preparation of intermediate C-5:

[0148] Intermediate B-5 (26.73 g, 80 mmol), compound c-5 (17.59 g, 96 mmol) and cesium carbonate (39.10 g, 120 mmol) were dissolved in DMF (800 mL), and refluxing was performed under nitrogen for 8 hours. After the reaction was completed, the mixture was poured into ice water, and the filter cake was recrystallized from dichloromethane and methanol to obtain intermediate C-5 (36.14 g, yield 90.85%), which had a solid purity of ≧99.75% as determined by HPLC. Mass spectrum m / z: 497.0102 (theoretical value: 497.0088).

[0149] Preparation of intermediate D-5:

[0150] Intermediate C-5 (24.86 g, 50 mmol), compound d-5 (19.28 g, 110 mmol) and cesium carbonate (53.76 g, 165 mmol) were dissolved in DMF (625 mL) and refluxed under nitrogen for 9 hours. After the reaction was completed, the mixture was poured into ice water and filtered under reduced pressure. The filter cake was recrystallized with dichloromethane and methanol to obtain intermediate D-5 (36.70 g, yield 90.98%), which had a solid purity of > 99.75% as determined by HPLC. Mass spectrum m / z: 806.2361 (theoretical value: 806.2375).

[0151] Preparation of compound 5:

[0152] Intermediate D-5 (24.20 g, 30 mmol) was dissolved in tert-butyl benzene (510 mL) and n-butyllithium (18 mL, 45 mmol, 2.5 M n-hexane solution) was added dropwise at 0°C under nitrogen, and then the temperature was raised to 70°C and stirring was maintained for 2 hours. After cooling to 0°C, BBr3(5.75 mL, 60 mmol) was added dropwise. The reaction system was returned to room temperature and stirring was maintained for 1 hour. N,N-diisopropylethylamine (9.90 mL, 60 mmol, DIEA) was added dropwise again at 0°C, and the reaction system was heated to 150°C and stirring was maintained for 12 hours. After the reaction was completed, the reaction was quenched with 51 mL of methanol, and then washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (petroleum ether / dichloromethane = 4 / 1) to obtain compound 5 (7.24 g, yield 35.05%), which had a solid purity of > 99.97% as determined by HPLC. Mass spectrum m / z: 688.3279 (theoretical value: 688.3267). Theoretical elemental content (%) C 48 H 13 D 15 BN3O: C, 83.72; H, 6.29; N, 6.10. Found elemental content (%): C, 83.69; H, 6.31; N, 6.08.

[0153] Synthesis Example 2: Preparation of compound 8

[0154]

[0155] Compound 8 (9.55 g, yield 35.25%) was obtained by replacing a-5 with an equimolar amount of a-8 and d-5 with an equimolar amount of d-8 according to the same preparation method as in Synthesis Example 1. The HPLC purity was > 99.96%. Mass spectrum m / z: 902.5138 (theoretical value: 902.5143). Theoretical elemental content (%) C 64 H 55D5BN3O: C, 85.12; H, 7.25; N, 4.65. Found (%): C, 85.08; H, 7.30; N, 4.70.

[0156] Synthesis Example 3: Preparation of compound 15

[0157]

[0158] Compound 15 (10.16 g, yield 35.18%) was obtained according to the same preparation method as synthesis example 1 by replacing d-5 with equimolar d-15. HPLC purity > 99.95%. Mass spectrum m / z: 962.3892 (theoretical value: 961.3907). Theoretical elemental content (%) C 60 H 60 BN3OSi4: C, 74.89; H, 6.28; N, 4.37. Found elemental content (%) C, 74.92; H, 6.31; N, 4.41.

[0159] Synthesis Example 4: Preparation of compound 17

[0160]

[0161] Compound 17 (7.71 g, yield 35.20%) was obtained according to the same preparation method as synthesis example 1 by replacing d-5 with equimolar d-17. HPLC purity > 99.97%. Mass spectrum m / z: 729.2938 (theoretical value: 729.2951). Theoretical elemental content (%) C 52 H 36 BN3O: C, 85.59; H, 4.97; N, 5.76. Found elemental content (%) C, 85.62; H, 5.02; N, 5.81.

[0162] Synthesis Example 5: Preparation of compound 21

[0163]

[0164] Compound 21 (9.56 g, yield 35.50%) was obtained according to the same preparation method as synthesis example 1 by replacing d-5 with equimolar d-8. HPLC purity > 99.94%. Mass spectrum m / z: 897.4838 (theoretical value: 897.4829). Theoretical elemental content (%) C 64 H 60 BN3O: C, 85.60; H, 6.73; N, 4.68. Found elemental content (%) C, 85.56; H, 6.69; N, 4.72.

[0165] Synthesis Example 6: Preparation of compound 27

[0166]

[0167] Following the same preparation method as synthesis example 1, d-5 was replaced with equimolar of d-27 to obtain compound 27 (11.83 g, yield 32.58%). HPLC purity > 99.96%. Mass spectrum m / z: 1209.6716 (theoretical value: 1209.6707). Theoretical elemental content (%) C 88 H 84 BN3O: C, 87.32; H, 6.99; N, 3.47. Measured elemental content (%) : C, 87.29; H, 7.03; N, 3.52.

[0168] Synthesis Example 7: Preparation of compound 27

[0169]

[0170] Following the same preparation method as synthesis example 1, d-5 was replaced with equimolar of d-34 to obtain compound 34 (10.37 g, yield 35.35%). HPLC purity > 99.97%. Mass spectrum m / z: 977.3589 (theoretical value: 977.3577). Theoretical elemental content (%) C 72 H 44 BN3O: C, 88.43; H, 4.54; N, 4.30. Measured elemental content (%) : C, 88.39; H, 4.49; N, 4.27.

[0171] Synthesis Example 8: Preparation of compound 36

[0172]

[0173] Following the same preparation method as synthesis example 1, d-5 was replaced with equimolar of d-36 to obtain compound 36 (10.56 g, yield 35.28%). HPLC purity > 99.94%. Mass spectrum m / z: 997.4833 (theoretical value: 997.4833). Theoretical elemental content (%) C 72 H 24 D 20 BN3O: C, 86.64; H, 6.46; N, 4.21. Measured elemental content (%) : C, 86.59; H, 6.50; N, 4.18.

[0174] Synthesis Example 9: Preparation of compound 37

[0175]

[0176] Following the same preparation method as in the synthesis example 1, d-5 was replaced by an equimolar amount of d-37 to obtain compound 37 (11.37 g, yield 35.16%). HPLC purity > 99.96%. Mass spectrum m / z: 1077.3401 (theoretical value: 1077.3387). Theoretical elemental content (%) C 76 H 40 BN7O: C, 84.68; H, 3.74; N, 9.10. Found elemental content (%) : C, 84.72; H, 3.69; N, 9.06.

[0177] Synthesis example 10: Preparation of compound 40

[0178]

[0179] Following the same preparation method as in the synthesis example 1, d-5 was replaced by an equimolar amount of d-40 to obtain compound 40 (10.98 g, yield 35.38%). HPLC purity > 99.94%. Mass spectrum m / z: 1033.4191 (theoretical value: 1033.4203). Theoretical elemental content (%) C 76 H 52 BN3O: C, 88.28; H, 5.07; N, 4.06. Found elemental content (%) : C, 88.31; H, 5.11; N, 4.10.

[0180] Synthesis example 11: Preparation of compound 48

[0181]

[0182] Following the same preparation method as in the synthesis example 1, d-5 was replaced by an equimolar amount of d-48 to obtain compound 48 (10.36 g, yield 35.18%). HPLC purity > 99.94%. Mass spectrum m / z: 981.3401 (theoretical value: 981.3387). Theoretical elemental content (%) C 68 H 40 BN7O: C, 83.18; H, 4.11; N, 9.99. Found elemental content (%) : C, 83.21; H, 4.07; N, 10.02.

[0183] Synthesis example 12: Preparation of compound 55

[0184]

[0185] Following the same preparation method as in the synthesis example 1, d-5 was replaced by equimolar of d-55 to obtain compound 55 (7.05 g, yield 34.78%). HPLC purity > 99.93%. Mass spectrum m / z: 675.2218 (theoretical value: 675.2230). Theoretical elemental content (%) C 46 H 26 BN5O: C, 81.79; H, 3.88; N, 10.37. Found elemental content (%) C, 81.82; H, 3.93; N, 10.41.

[0186] Synthesis example 13: Preparation of compound 57

[0187]

[0188] Following the same preparation method as in the synthesis example 1, d-5 was replaced by equimolar of d-57 to obtain compound 57 (9.21 g, yield 35.12%). HPLC purity > 99.95%. Mass spectrum m / z: 873.2963 (theoretical value: 873.2951). Theoretical elemental content (%) C 64 H 36 BN3O: C, 87.97; H, 4.15; N, 4.81. Found elemental content (%) C, 88.02; H, 4.20; N, 4.78.

[0189] Synthesis example 14: Preparation of compound 81

[0190]

[0191] Following the same preparation method as in the synthesis example 1, c-5 was replaced by equimolar of c-81, d-5 was replaced by equimolar of d-8 to obtain compound 81 (10.89 g, yield 34.56%). HPLC purity > 99.95%. Mass spectrum m / z: 1049.5442 (theoretical value: 1049.5455). Theoretical elemental content (%) C 76 H 68 BN3O: C, 86.92; H, 6.53; N, 4.00. Found elemental content (%) C, 86.89; H, 6.48; N, 4.96.

[0192] Synthesis example 15: Preparation of compound 113

[0193]

[0194] Following the same preparation method as in the synthesis example 1, a-5 was replaced with equimolar of a-113, d-5 was replaced with equimolar of d-8 to obtain compound 113 (10.91 g, yield 35.24%). HPLC purity > 99.97%. Mass spectrum m / z: 1031.5942 (calcd: 1031.5925). Theoretical elemental content (%) C 74 H 74 BN3O: C, 86.11; H, 7.23; N, 4.07. Found elemental content (%) C, 86.08; H, 7.19; N, 4.11.

[0195] Synthesis example 16: Preparation of compound 124

[0196]

[0197] Following the same preparation method as in the synthesis example 1, a-5 was replaced with equimolar of a-124, d-5 was replaced with equimolar of d-124 to obtain compound 124 (7.96 g, yield 35.39%). HPLC purity > 99.95%. Mass spectrum m / z: 749.2624 (calcd: 749.2638). Theoretical elemental content (%) C 54 H 32 BN3O: C, 86.52; H, 4.30; N, 5.61. Found elemental content (%) C, 86.48; H, 4.27; N, 5.58.

[0198] Synthesis example 17: Preparation of compound 126

[0199]

[0200] Following the same preparation method as in the synthesis example 1, a-5 was replaced with equimolar of a-126, d-5 was replaced with equimolar of d-8 to obtain compound 126 (10.35 g, yield 35.43%). HPLC purity > 99.94%. Mass spectrum m / z: 973.5130 (calcd: 973.5142). Theoretical elemental content (%) C 70 H 64 BN3O: C, 86.31; H, 6.62; N, 4.31. Found elemental content (%) C, 86.28; H, 6.58; N, 4.27.

[0201] Synthesis example 18: Preparation of compound 141

[0202]

[0203] Following the same preparation method as in Synthesis Example 1, a-5 was replaced with an equimolar amount of a-141, and d-5 was replaced with an equimolar amount of d-8, yielding compound 141 (11.13 g, yield 35.32%). HPLC purity ≥ 99.96%. Mass spectrometry m / z: 1049.5442 (theoretical value: 1049.5455). Theoretical elemental content (%) C 76 H 68 BN3O: C, 86.92; H, 6.53; N, 4.00. Measured elemental content (%): C, 86.89; H, 6.49; N, 3.96.

[0204] Synthetic Example 19: Preparation of Compound 156

[0205]

[0206] Following the same preparation method as in Synthesis Example 1, a-5 was replaced with an equimolar amount of a-156, and d-5 was replaced with an equimolar amount of d-8, yielding compound 156 (10.08 g, yield 35.20%). HPLC purity ≥ 99.94%. Mass spectrometry m / z: 953.5441 (theoretical value: 953.5455). Theoretical elemental content (%) C 68 H 68 BN3O: C, 85.60; H, 7.18; N, 4.40. Measured elemental content (%): C, 85.57; H, 7.14; N, 4.36.

[0207] Synthesis Example 20: Preparation of Compound 162

[0208]

[0209] Following the same preparation method as in Synthesis Example 1, a-5 was replaced with an equimolar amount of a-162, and d-5 was replaced with an equimolar amount of d-8, yielding compound 162 (9.48 g, yield 35.14%). HPLC purity ≥ 99.96%. Mass spectrometry m / z: 898.4778 (theoretical value: 898.4782). Theoretical elemental content (%) C 63 H 59 BN4O: C, 84.17; H, 6.62; N, 6.23. Measured elemental content (%): C, 84.21; H, 6.58; N, 6.19.

[0210] Synthesis Example 21: Preparation of Compound 164

[0211]

[0212] Following the same preparation method as in the synthesis example 1, a-5 was replaced by equimolar of a-164, d-5 was replaced by equimolar of d-8, compound 164 (10.04 g, yield 35.29%) was obtained. HPLC purity > 99.93%. Mass spectrum m / z: 947.4974 (theoretical value: 947.4986). Theoretical elemental content (%) C 68 H 62 BN3O: C, 86.15; H, 6.59; N, 4.43. Found elemental content (%) : C, 86.20; H, 6.63; N, 4.39.

[0213] Synthesis example 22: Preparation of compound 164

[0214]

[0215] Following the same preparation method as in the synthesis example 1, a-5 was replaced by equimolar of a-169, d-5 was replaced by equimolar of d-8, compound 169 (10.39 g, yield 35.34%) was obtained. HPLC purity > 99.92%. Mass spectrum m / z: 979.5601 (theoretical value: 979.5601). Theoretical elemental content (%) C 70 H 70 BN3O: C, 85.78; H, 7.20; N, 4.29. Found elemental content (%) : C, 85.82; H, 7.17; N, 4.33.

[0216] Synthesis example 23: Preparation of compound 221

[0217]

[0218] Following the same preparation method as in the synthesis example 1, c-5 was replaced by equimolar of c-221, d-5 was replaced by equimolar of d-8, compound 221 (9.38 g, yield 34.21%) was obtained. HPLC purity > 99.94%. Mass spectrum m / z: 913.4589 (theoretical value: 913.4601). Theoretical elemental content (%) C 64 H 60 BN3S: C, 84.10; H, 6.62; N, 4.60. Found elemental content (%) : C, 84.07; H, 6.58; N, 4.56.

[0219] Synthesis example 24: Preparation of compound 228

[0220]

[0221] Following the same preparation method as in the synthesis example 1, replacing a-5 with equimolar of a-275, c-5 with equimolar of c-221, and d-5 with equimolar of d-8, compound 275 (10.31 g, yield 34.08%) was obtained. HPLC purity > 99.96%. Mass spectrum m / z: 1007.5401 (calcd: 1007.5384). Theoretical elemental content (%) C 88 H 76 BN3S: C, 84.01; H, 7.26; N, 4.32. Found elemental content (%) : C, 83.95; H, 7.31; N, 4.28.

[0222] Synthesis example 25: Preparation of compound 267

[0223]

[0224] Following the same preparation method as in the synthesis example 1, replacing a-5 with equimolar of a-267, c-5 with equimolar of c-267, and d-5 with equimolar of d-8, compound 267 (9.98 g, yield 34.23%) was obtained. HPLC purity > 99.95%. Mass spectrum m / z: 971.5371 (calcd: 971.5384). Theoretical elemental content (%) C 68 H 70 BN3S: C, 84.01; H, 7.26; N, 4.32. Found elemental content (%) : C, 83.95; H, 7.31; N, 4.28.

[0225] Synthesis example 26: Preparation of compound 274

[0226]

[0227] Following the same preparation method as in the synthesis example 1, replacing a-5 with equimolar of a-274, c-5 with equimolar of c-221, and d-5 with equimolar of d-8, compound 274 (10.31 g, yield 34.08%) was obtained. HPLC purity > 99.96%. Mass spectrum m / z: 1007.5401 (calcd: 1007.5384). Theoretical elemental content (%) C 71 H 70 BN3S: C, 84.01; H, 7.26; N, 4.32. Found elemental content (%) : C, 83.95; H, 7.31; N, 4.28.

[0228] Synthesis example 27: Preparation of compound 275

[0229]

[0230] Following the same preparation method as in the synthesis example 1, replacing a-5 with equimolar of a-275, c-5 with equimolar of c-221, d-5 with equimolar of d-8, compound 275 (9.67 g, yield 33.78%) was obtained. HPLC purity > 99.96%. Mass spectrum m / z: 953.4921 (theoretical value: 953.4914). Theoretical elemental content (%) C 67 H 64 BN3S: C, 84.34; H, 6.76; N, 4.40. Found elemental content (%) C, 84.29; H, 6.73; N, 4.35.

[0231] Synthesis example 28: Preparation of compound 349

[0232]

[0233] Following the same preparation method as in the synthesis example 1, replacing c-5 with equimolar of c-349, d-5 with equimolar of d-349, compound 349 (9.21 g, yield 33.21%) was obtained. HPLC purity > 99.96%. Mass spectrum m / z: 923.5338 (theoretical value: 923.5350). Theoretical elemental content (%) C 67 H 66 BN3: C, 87.08; H, 7.20; N, 4.55. Found elemental content (%) C, 87.12; H, 7.17; N, 4.60.

[0234] Synthesis example 29: Preparation of compound 412

[0235]

[0236] Following the same preparation method as in the synthesis example 1, replacing c-5 with equimolar of d-124, d-5 with equimolar of c-5, compound 412 (6.75 g, yield 32.65%) was obtained. HPLC purity > 99.94%. Mass spectrum m / z: 689.2262 (theoretical value: 689.2275). Theoretical elemental content (%) C 48 H 28 BN3O2: C, 83.61; H, 4.09; N, 6.09. Found elemental content (%) C, 83.58; H, 4.13; N, 6.14.

[0237] Synthesis example 30: Preparation of compound 463

[0238]

[0239] Following the same preparation method as in the synthesis example 1, c-5 was replaced by equimolar of d-8, d-5 was replaced by equimolar of c-5 to obtain compound 463 (7.93 g, yield 32.98 %). HPLC purity > 99.96 %. Mass spectrum m / z: 801.3514 (theoretical value: 801.3527). Theoretical elemental content (%) C 56 H 44 BN3O2: C, 83.89; H, 5.53; N, 5.24. Found elemental content (%) : C, 83.93; H, 5.49; N, 5.19.

[0240] Synthesis example 31: Preparation of compound 472

[0241]

[0242] Following the same preparation method as in the synthesis example 1, c-5 was replaced by equimolar of d-8, d-5 was replaced by equimolar of c-5 to obtain compound 463 (7.93 g, yield 32.98 %). HPLC purity > 99.96 %. Mass spectrum m / z: 801.3514 (theoretical value: 801.3527). Theoretical elemental content (%) C 60 H 36 BN3O2: C, 83.89; H, 5.53; N, 5.24. Found elemental content (%) : C, 83.93; H, 5.49; N, 5.19.

[0243] Synthesis example 32: Preparation of compound 478

[0244]

[0245] Following the same preparation method as in the synthesis example 1, c-5 was replaced by equimolar of d-8, d-5 was replaced by equimolar of c-5 to obtain compound 463 (7.93 g, yield 32.98 %). HPLC purity > 99.96 %. Mass spectrum m / z: 801.3514 (theoretical value: 801.3527). Theoretical elemental content (%) C 68 H 56 BN3O2: C, 83.89; H, 5.53; N, 5.24. Found elemental content (%) : C, 83.93; H, 5.49; N, 5.19.

[0246] Synthesis example 33: Preparation of compound 481

[0247]

[0248] Following the same preparation method as in the synthesis example 1, replacing c-5 with equimolar of d-481, d-5 with equimolar of c-5, compound 481 (9.05 g, yield 31.63%) was obtained. HPLC purity > 99.96%. Mass spectrum m / z: 953.2329 (theoretical value: 953.2342). Theoretical elemental content (%) C 64 H 36 BN3O2S2: C, 80.58; H, 3.80; N, 4.40. Found elemental content (%) C, 80.62; H, 3.76; N, 4.35.

[0249] Synthesis example 34: Preparation of compound 509

[0250]

[0251] Following the same preparation method as in the synthesis example 1, replacing a-5 with equimolar of a-509, c-5 with equimolar of d-8, d-5 with equimolar of c-5, compound 509 (8.74 g, yield 32.98%) was obtained. HPLC purity > 99.93%. Mass spectrum m / z: 882.4168 (theoretical value: 882.4153). Theoretical elemental content (%) C 62 H 43 D5BN3O2: C, 84.34; H, 6.05; N, 4.76. Found elemental content (%) C, 84.29; H, 6.10; N, 4.81.

[0252] Synthesis example 35: Preparation of compound 534

[0253]

[0254] Following the same preparation method as in the synthesis example 1, replacing a-5 with equimolar of a-534, c-5 with equimolar of d-8, d-5 with equimolar of c-5, compound 534 (8.05 g, yield 31.86%) was obtained. HPLC purity > 99.96%. Mass spectrum m / z: 841.3492 (theoretical value: 841.3476). Theoretical elemental content (%) C 58 H 44 BN3O3: C, 82.75; H, 5.27; N, 4.99. Found elemental content (%) C, 82.72; H, 5.31; N, 5.03.

[0255] Synthesis example 36: Preparation of compound 575

[0256]

[0257] Following the same preparation method as in the synthesis example 1, c-5 was replaced by equimolar of d-8, d-5 was replaced by equimolar of c-221 to obtain compound 575 (7.90 g, yield 31.58%). HPLC purity > 99.95%. Mass spectrum m / z: 833.3056 (theoretical value: 833.3070). Theoretical elemental content (%) C56H44BN3S2: C, 80.66; H, 5.32; N, 5.04. Found elemental content (%) : C, 80.70; H, 5.28; N, 4.99.

[0258] Synthesis example 37: Preparation of compound 690

[0259]

[0260] Following the same preparation method as in the synthesis example 1, d-5 was replaced by equimolar of c-5 to obtain compound 690 (6.57 g, yield 31.02%). HPLC purity > 99.94%. Mass spectrum m / z: 705.2236 (theoretical value: 705.2224). Theoretical elemental content (%) C48H28BN3O3: C, 81.71; H, 4.00; N, 5.96. Found elemental content (%) : C, 81.68; H, 3.96; N, 6.00.

[0261] Synthesis example 38: Preparation of compound 715

[0262]

[0263] Following the same preparation method as in the synthesis example 1, c-5 was replaced by equimolar of c-715, d-5 was replaced by equimolar of c-715 to obtain compound 715 (10.02 g, yield 32.05%). HPLC purity > 99.96%. Mass spectrum m / z: 1041.5967 (theoretical value: 1041.5980). Theoretical elemental content (%) C 72 H 76 BN3O3: C, 82.98; H, 7.35; N, 4.03. Found elemental content (%) : C, 83.02; H, 7.40; N, 3.98.

[0264] Synthesis example 39: Preparation of compound 797

[0265]

[0266] Following the same preparation method as in the synthesis of Example 1, c-5 was replaced by equimolar of c-797, d-5 was replaced by equimolar of c-797, to give compound 797 (7.7 g, yield 30.65%). HPLC purity > 99.95%. Mass spectrum m / z: 837.2492 (theoretical value: 837.2477). Theoretical elemental content (%) C 54 H 40 BN3S3: C, 77.40; H, 4.81; N, 5.01. Found elemental content (%) C, 77.36; H, 4.78; N, 4.97.

[0267] Synthesis Example 40: Preparation of compound 837

[0268]

[0269] Preparation of intermediate A-837:

[0270] Compound h-837 (34.11 g, 150 mmol), compound a-5 (21.95 g, 180 mmol) and potassium carbonate (37.32 g, 270 mmol) were dissolved in a mixed solution of THF and water 675 mL (volume ratio 4: 1), Pd(PPh3)4(5.20 g, 4.5 mmol) was added under nitrogen, and stirred at reflux for 12 hours. After the reaction was completed, washed with dichloromethane and water, the organic phase was concentrated, and purified by column chromatography (eluent: petroleum ether) to obtain intermediate A-837 (31.15 g, yield 92.45%), HPLC detected solid purity > 99.84%. Mass spectrum m / z: 224.0189 (theoretical value: 224.0204).

[0271] Preparation of intermediate B-837:

[0272] Intermediate A-837 (22.46 g, 100 mmol), compound b-11 (54.16 g, 220 mmol) and cesium carbonate (107.52 g, 330 mmol) were dissolved in DMF (1250 mL), and stirred at reflux under nitrogen for 9 hours. After the reaction was completed, the mixture was poured into ice water, and filtered under reduced pressure, and the filter cake was recrystallized with dichloromethane and methanol to obtain intermediate B-837 (62.59 g, yield 92.45%), HPLC detected solid purity > 99.88%. Mass spectrum m / z: 677.9868 (theoretical value: 677.9880).

[0273] Preparation of intermediate C-837:

[0274] Intermediate B-837 (54.16 g, 80 mmol) was dissolved in tert-butyl benzene (1350 mL) and n-butyllithium (48 mL, 120 mmol, 2.5 M in n-hexane) was added dropwise at 0 °C under nitrogen. The reaction was then warmed to 70 °C and stirred for 2 h. After cooling to 0 °C, BBr3(15.33 mL, 160 mmol) was added dropwise. The reaction was allowed to warm to room temperature and stirred for 1 h. N,N-diisopropylethylamine (26.40 mL, 160 mmol, DIEA) was added dropwise at 0 °C and the reaction was heated to 150 °C and stirred for 12 h. After the reaction was complete, the reaction was quenched with 135 mL of methanol and washed with dichloromethane and water. The organic phase was concentrated and purified by column chromatography (eluent: petroleum ether / dichloromethane = 4 / 1) to give intermediate C-837 (17.43 g, 33.50% yield) with a solid purity of > 99.75% by HPLC. Mass (m / z): 652.0141 (calculated: 652.0128). Preparation of intermediate D-837:

[0275] Intermediate C-837 (13.01 g, 20 mmol) and NBS (3.56 g, 20 mmol) were dissolved in chloroform 450 mL under nitrogen and stirred at room temperature for 12 h. After the reaction was complete, the solvent was evaporated and the residue was purified by column chromatography on neutral silica gel (eluent: dichloromethane and petroleum ether) to give intermediate D-837 (12.46 g, 85.45% yield) with a purity of 99.86% by HPLC and mass (m / z): 729.9246 (calculated: 729.9233). Preparation of compound 837:

[0276] Intermediate D-837 (7.29 g, 10 mmol) and compound e-11 (5.74 g, 20 mmol) were dissolved in a mixture of tetrahydrofuran and water 80 mL (3:1 by volume) under nitrogen and Pd(PPh3)4(0.35 g, 0.3 mmol), potassium carbonate (5.53 g, 40 mmol) were added. The reaction was refluxed for 12 h. After the reaction was complete, the reaction was cooled to room temperature, filtered and the solvent was evaporated. The residue was purified by column chromatography on neutral silica gel (eluent: dichloromethane and petroleum ether) to give compound 837 (6.11 g, 68.50% yield) with a solid purity of > 99.96% by HPLC and mass (m / z): 893.1001 (calculated: 893.1020). Theoretical elemental content (%) 54 H 32 BN3Se2: C, 72.74; H, 3.62; N, 4.71. Found: C, 72.69; H, 3.58; N, 4.68.

[0277] Synthesis Example 41: Preparation of compound 874

[0278]

[0279] Following the same procedure of synthesis example 41, replacing b-837 with equimolar of c-5, e-837 with equimolar of e-874, compound 874 (5.28 g, yield 68.98%) was obtained. HPLC purity > 99.96%. Mass spectrum m / z: 765.2565 (calcd 765.2588). Anal. Calcd for C42H42N8O8· 1.0 H2O (%): C, 64.71; H, 5.62; N, 13.62. Found: C, 64.68; H, 5.59; N, 13.65. 54 H 32 BN3O2: C, 84.71; H, 4.21; N, 5.49. Anal. Found (%): C, 84.68; H, 4.17; N, 5.53.

[0280] Synthesis Example 42: Preparation of compound 879

[0281]

[0282] Preparation of intermediate A-879:

[0283] Compound h-879 (49.08 g, 200 mmol), compound a-5 (29.26 g, 240 mmol) and potassium carbonate (49.76 g, 360 mmol) were dissolved in a mixed solution of THF and water 900 mL (volume ratio 4:1), Pd(PPh3)4(6.93 g, 6.0 mmol) was added under nitrogen, and stirred at reflux for 13 hours. After the reaction was completed, washed with dichloromethane and water, the organic phase was concentrated, and purified by column chromatography (eluent: petroleum ether) to obtain intermediate A-879 (46.24 g, yield 95.30%), HPLC detected solid purity > 99.81%. Mass spectrum m / z: 242.0093 (theoretical value: 242.0110).

[0284] Preparation of intermediate AA-879:

[0285] Compound A-879 (36.39 g, 150 mmol), compound a-5 (21.95 g, 180 mmol) and potassium carbonate (37.32 g, 270 mmol) were dissolved in a mixed solution of THF and water 675 mL (volume ratio 4:1), Pd(PPh3)4(5.20 g, 4.5 mmol) was added under nitrogen, and stirred at reflux for 12 hours. After the reaction was completed, washed with dichloromethane and water, the organic phase was concentrated, and purified by column chromatography (eluent: petroleum ether) to obtain intermediate AA-879 (37.31 g, yield 87.50%), HPLC detected solid purity > 99.89%. Mass spectrum m / z: 284.0831 (theoretical value: 284.0813).

[0286] Preparation of intermediate B-879:

[0287] Compound AA-879 (28.43 g, 100 mmol) was dissolved in 335 mL of tetrahydrofuran solution, lithium diisopropylamide (LDA, 50 mL, 100 mmol, 2M tetrahydrofuran solution) was added dropwise under nitrogen at -20°C, stirring was maintained for 1 hour, then iodine (25.38 g, 100 mmol) was added, and the temperature was returned to room temperature, and stirring was continued for 4 hours. After the reaction was completed, the mixture was washed with sodium thiosulfate solution and dichloromethane, and the organic phase was concentrated and purified by column chromatography (eluent: petroleum ether) to obtain intermediate B-879 (33.43 g, yield 81.50%), which had a solid purity of ≧99.81% as determined by HPLC. Mass spectrum m / z: 409.9765 (theoretical value: 409.9779).

[0288] Preparation of intermediate C-879:

[0289] Intermediate B-879 (32.81 g, 80 mmol), compound c-5 (17.59 g, 96 mmol), and cesium carbonate (39.10 g, 120 mmol) were dissolved in DMF (800 mL) and refluxed under nitrogen for 8 hours. After the reaction was completed, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized with dichloromethane and methanol to obtain intermediate C-879 (39.10 g, yield 85.25%), which had a solid purity of ≧99.83% as determined by HPLC. Mass spectrum m / z: 573.03988 (theoretical value: 573.0401).

[0290] Preparation of intermediate D-879:

[0291] Intermediate C-879 (28.67 g, 50 mmol), compound b-11 (30.74 g, 110 mmol), and cesium carbonate (53.76 g, 165 mmol) were dissolved in DMF (625 mL) and refluxed under nitrogen for 9 hours. After the reaction was completed, the mixture was poured into ice water, filtered under reduced pressure, and the filter cake was recrystallized with dichloromethane and methanol to obtain intermediate D-879 (47.73 g, yield 87.40%), which had a solid purity of ≧99.86% as determined by HPLC. Mass spectrum m / z: 1091.4236 (theoretical value: 1091.4251).

[0292] Preparation of compound 879:

[0293] Intermediate D-879 (32.77 g, 30 mmol) was dissolved in tert-butyl benzene (510 mL), and n-butyllithium (18 mL, 45 mmol, 2.5 M n-hexane solution) was added dropwise at 0 °C under nitrogen, and then the temperature was raised to 70 °C and stirring was maintained for 2 hours. After cooling to 0 °C, BBr3(5.75 mL, 60 mmol) was added dropwise. The reaction system was returned to room temperature and stirring was maintained for 1 hour, and N,N-diisopropylethylamine (9.90 mL, 60 mmol, DIEA) was added dropwise again at 0 °C, and the reaction system was heated to 150 °C and stirring was maintained for 12 hours. After the reaction was completed, the reaction was quenched using 50 mL of methanol, and then washed with dichloromethane and water, and the organic phase was concentrated and purified by column chromatography (eluent: petroleum ether / dichloromethane = 4 / 1) to obtain compound 879 (9.50 g, yield 32.50%), and the solid purity was ≧99.96% by HPLC. Mass m / z: 973.5129 (theoretical value: 973.5142). Theoretical elemental content (%) C 70 H 64 BN3O: C, 86.31; H, 6.62; N, 4.31. Found elemental content (%): C, 86.28; H, 6.58; N, 4.27.

[0294] Device Example 1-1:

[0295] First, the ITO (10 nm) / Ag (100 nm) / ITO (10 nm) glass substrate was cleaned in distilled water for 2 times, ultrasonic washing for 30 minutes, and then cleaned in distilled water for 2 times, ultrasonic washing for 10 minutes. After the distilled water cleaning was completed, the substrate was dried on a hot plate heated to 120 °C, and then transferred to a plasma cleaning machine and washed for 5 minutes. Then, the substrate was transferred to an evaporation machine.

[0296] Then, 10 nm-thick HI-1 and HT-1 were vacuum-deposited on the glass substrate as a hole injection layer, the mass ratio of HI-1 to HT-1 being 3:97, 120 nm-thick HT-1 was vacuum-deposited on the hole injection layer as a hole transport layer, 25 nm-thick light-emitting layer was vacuum-deposited on the hole transport layer, the light-emitting layer structure comprising H-1 as a host material and compound 5 as a dopant material, the mass ratio of H-1 to compound 5 being 96:4, then 35 nm-thick ET-1 and Liq were vacuum-deposited on the light-emitting layer as an electron transport layer, the mass ratio of ET-1 to Liq being 1:1, 1 nm-thick Yb was vacuum-deposited on the electron transport layer as an electron injection layer, then 15 nm-thick Mg:Ag (the mass ratio of Mg to Ag being 1:9) alloy was vacuum-deposited on the electron injection layer as a cathode, then CP-1 was vacuum-deposited on the cathode as a capping layer, the thickness being 70 nm, thereby preparing an organic electroluminescent device.

[0297]

[0298] Device Example 1-2 to Device Example 1-42:

[0299] An organic electroluminescent device was prepared in the same manner as in Device Example 1-1, except that compound 8, compound 15, compound 17, compound 21, compound 27, compound 34, compound 36, compound 37, compound 40, compound 48, compound 55, compound 57, compound 81, compound 113, compound 124, compound 126, compound 141, compound 156, compound 162, compound 164, compound 169, compound 221, compound 228, compound 267, compound 274, compound 275, compound 349, compound 412, compound 463, compound 472, compound 478, compound 481, compound 509, compound 534, compound 575, compound 690, compound 715, compound 797, compound 837, compound 874, and compound 879 of the present application were used instead of compound 5 in the light-emitting layer as a dopant material.

[0300] Comparative Examples 1 to 5:

[0301] An organic electroluminescent device was prepared in the same manner as in Device Example 1-1, except that comparative compound 1, comparative compound 2, comparative compound 3, comparative compound 4, and comparative compound 5 were used instead of compound 5 in the light-emitting layer as a dopant material.

[0302] A combined IVL test system consisting of test software, a computer, a K2400 digital source meter manufactured by Keithley, and a PR788 spectral scan luminance meter manufactured by Photo Research was used to test the luminous efficiency of the organic electroluminescent device. An M6000 OLED lifetime test system manufactured by McScience was used to test the lifetime of the organic electroluminescent device. The test environment was an atmospheric environment, and the temperature was room temperature. The results of the luminous characteristic tests of the organic electroluminescent devices obtained in Device Examples 1-1 to 1-42 and Comparative Examples 1 to 5 of the present invention are shown in Table 1 below.

[0303] Table 1: Luminous characteristic tests of organic electroluminescent devices

[0304]

[0305]

[0306] Device Example 2-1:

[0307] First, an ITO (10 nm) / Ag (100 nm) / ITO (10 nm) glass substrate was cleaned in distilled water twice, ultrasonically washed for 30 minutes, and then cleaned in distilled water twice again, ultrasonically washed for 10 minutes. After the cleaning in distilled water was completed, the substrate was dried on a hot plate heated to 120°C, transferred to a plasma cleaner, washed for 5 minutes, and then transferred to an evaporation machine.

[0308] Then, HI-1 and HT-1 were evaporated on the glass substrate to a thickness of 10 nm as a hole injection layer, and the mass ratio of HI-1 to HT-1 was 3:97. HT-1 was evaporated on the hole injection layer to a thickness of 120 nm as a hole transport layer. A light-emitting layer was formed by evaporating H-1 as a host material and compound 5 as a dopant material, and the mass ratio of H-1 to compound 5 was 96:4, and the thickness of the light-emitting layer was 25 nm. Sensitizer Ir(PPy)3 was evaporated at a doping amount of 10 wt% based on the total amount of the host and the dopant. Then, ET-1 and Liq were evaporated on the light-emitting layer to a thickness of 35 nm as an electron transport layer, and the mass ratio of ET-1 to Liq was 1:1. Yb was evaporated on the electron transport layer to a thickness of 1 nm as an electron injection layer. Then, an Mg:Ag (mass ratio of Mg to Ag was 1:9) alloy was evaporated on the electron injection layer to a thickness of 15 nm as a cathode. Then, CP-1 was evaporated on the cathode as a capping layer, and the thickness was 70 nm, thereby preparing an organic electroluminescent device.

[0309] Device Example 2-2 to Device Example 2-42:

[0310] An organic electroluminescent device was produced in the same manner as in Device Example 2-1, except that Compound 8, Compound 15, Compound 17, Compound 21, Compound 27, Compound 34, Compound 36, Compound 37, Compound 40, Compound 48, Compound 55, Compound 57, Compound 81, Compound 113, Compound 124, Compound 126, Compound 141, Compound 156, Compound 162, Compound 164, Compound 169, Compound 221, Compound 228, Compound 267, Compound 274, Compound 275, Compound 349, Compound 412, Compound 463, Compound 472, Compound 478, Compound 481, Compound 509, Compound 534, Compound 575, Compound 690, Compound 715, Compound 797, Compound 837, Compound 874, Compound 879 of the present application were used instead of Compound 5 in the light-emitting layer as a dopant material.

[0311] Comparative Examples 1 to 5:

[0312] An organic electroluminescent device was produced in the same manner as in Device Example 2-1, except that Comparative Compound 1, Comparative Compound 2, Comparative Compound 3, Comparative Compound 4, Comparative Compound 5 were used instead of Compound 5 in the light-emitting layer as a dopant material.

[0313] A combined IVL test system consisting of test software, a computer, a K2400 digital source meter produced by Keithley Corporation, USA, and a PR788 spectral scan luminance meter by Photo Research Corporation, USA was used to test the luminous efficiency of the organic electroluminescent device. An M6000 OLED lifetime test system by McScience Corporation was used to test the lifetime of the organic electroluminescent device. The test environment was atmospheric environment and the temperature was room temperature. The results of the luminescent property test of the organic electroluminescent device obtained in Device Examples 2-1 to 2-42 and Comparative Examples 1 to 5 of the present application are shown in Table 2 below.

[0314] Table 2: Luminescent property test of organic electroluminescent device

[0315]

[0316]

[0317]

[0318] According to the test results of Table 1 and Table 2 of the present application, compared with Comparative Compound 1-Comparative Compound 5, the boron-nitrogen compound provided by the present application has high color purity and luminous efficiency, and meanwhile, due to the specific position of boron atom and nitrogen atom in the rigid structure, resonance effect can be induced, so that the device life can be avoided from being sharply shortened due to thin film crystallization.

[0319] It should be noted that the present application is particularly described with individual embodiments, but those skilled in the art can make various forms or details of improvement on the present application without departing from the principles of the present application, and these improvements also fall within the protection scope of the present application.

Claims

1. A boron-nitrogen compound, characterized in that, The boron-nitrogen compound has the structure shown in Formula 1. The X1 and X2 that are the same or different are selected from single bonds, O, S, Se, N(R) a ), C(R b R b '), Si(R) b R b '), Ge(R) b R b One of the following, and at least one of X1 and X2 is not selected from single bonds; The R a It is selected from any one of the following: substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C60 aryl groups, substituted or unsubstituted C2-C60 heteroaryl groups, fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings; The R b R b 'The same or different from any one selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring; or R b R b The ' bonds can bond together to form substituted or unsubstituted rings; The w atoms, whether identical or different, are selected from C(R1) or N atoms; The R1 is selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring; or two adjacent R1s can be bonded to form a substituted or unsubstituted ring; The R0 is selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring; The Ar1 is selected from the structure shown in formula a-1; The X3 is selected from single bonds, O, S, Se, N(R) c ), C(R d R d '), Si(R) d R d '), Ge(R) d R d One of the following; The R c It is selected from any one of the following: substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C60 aryl groups, substituted or unsubstituted C2-C60 heteroaryl groups, fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings; The R d R d 'The same or different from any one selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring; or R d R d The ' bonds can bond together to form substituted or unsubstituted rings; The same or different v is selected from C(R2) or N atoms; R2 is selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring. R3 is selected from any one of the following: substituted or unsubstituted silyl group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C2-C60 heteroaryl group, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring, or the N atom corresponding to R3 is a bonding site with L1. The Ar2 is selected from any one of cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring; The L1 and L2 are the same or different and are selected from one of the following: single bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C2-C60 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings in a fused cycloalcoholic group, or substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroarylene rings in a fused cycloalcoholic group.

2. The boron-nitrogen compound according to claim 1, characterized in that, The boron-nitrogen compound is selected from any one of the following formulas 1-1 to 1-4. The X4 and X5 that are the same or different are selected from O, S, Se, N(R). a ), C(R b R b '), Si(R) b R b '), Ge(R) b R b One of the following; The w, v, R0, L1, L2, Ar2, R a R b R b The definitions of ', X3, and R3 are the same as those in Equation 1.

3. The boron-nitrogen compound according to claim 2, characterized in that, The boron-nitrogen compound is selected from any one of Formulas 2-1 to 2-10.

4. The boron-nitrogen compound according to claim 1, characterized in that, Formula a-1 is selected from any one of the following groups. The Rx, whether identical or different, is selected from any one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring; or adjacent Rx may be bonded to form a substituted or unsubstituted ring. The R3, R c R d R d The definitions of ' are all the same as those in claim 1 above; The n1 is selected from 0, 1, 2, 3 or 4, the n2 is selected from 0, 1, 2 or 3, and the n3 is selected from 0, 1 or 2.

5. The boron-nitrogen compound according to claim 1, characterized in that, The Ar2 is selected from cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, or any one of the following groups: The z that are the same or different are selected from C(R) n ) or N atom; The R n The same or different from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring; or two adjacent Rn can be bonded to form a substituted or unsubstituted ring; The ring H is selected from one of the substituted or unsubstituted C3 to C30 alicyclic rings; The X8 and X9 that are the same or different are selected from O, S, C(R). e R e '), N(R f One of them; The R e R e 'The same or different from any one selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring; or R e R e The ' bonds can bond together to form substituted or unsubstituted rings; The R f It is selected from any one of the following: substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C60 aryl groups, substituted or unsubstituted C2-C60 heteroaryl groups, fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings.

6. The boron-nitrogen compound according to claim 1, characterized in that, The L1 and L2 are selected from single bonds, or any one of the following groups: The R m The same or different from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring; or two adjacent R m They can bond together to form substituted or unsubstituted rings; The q1 is selected from 0, 1, 2, 3 or 4; the q2 is selected from 0, 1, 2 or 3; the q3 is selected from 0, 1 or 2; the q4 is selected from 0, 1, 2, 3, 4, 5 or 6; the q5 is selected from 0, 1, 2, 3, 4 or 5; the q6 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the q7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; and the q8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

7. The boron-nitrogen compound according to claim 1, characterized in that, The boron-nitrogen compound is selected from any of the following structures:

8. An organic electroluminescent device, characterized in that, The organic electroluminescent device comprises at least one or more of the boron nitride compounds according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that, The organic electroluminescent device includes a cathode, an anode, and an organic layer, wherein the organic layer is located between the cathode and the anode, and the organic layer contains a boron-nitrogen compound as described in any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 8, characterized in that, The organic electroluminescent device comprises a cathode, an anode, and an organic layer, wherein the organic layer is located between the cathode and the anode, and the organic layer contains a light-emitting layer, wherein the light-emitting layer contains a boron nitrogen compound as described in any one of claims 1 to 7.

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