Boron nitrogen compound, composition thereof and organic electroluminescent device

Abstract

The present invention discloses a boron nitrogen compound, a composition thereof and an organic electroluminescent device. The boron nitrogen compound of the present invention is shown in Formula I. The boron nitrogen compound of the present invention emits light in the green to red light region and has a narrow spectrum luminescence characteristic, and can also effectively adjust the emission wavelength to achieve fine control of the emission wavelength in the range of 493-613nm, and has good application prospects.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescence, and in particular relates to a boron nitrogen compound, a composition thereof and an organic electroluminescent device. Background Art

[0002] Organic electroluminescent technology has shown great application prospects in the fields of full-color display and solid-state white light illumination, and has received extensive research and attention in the scientific research community and the industry. Organic small molecule optoelectronic materials are widely used as high-performance electroluminescent materials due to their clear structure, easy modification, simple purification and processing. At present, traditional fluorescent dye molecules often have a very high photoluminescence quantum yield, but electroluminescent devices (OLED: Organic Light Emitting Devices) based on these fluorescent materials are subject to the limitation of 25% internal quantum efficiency. The external quantum efficiency of electroluminescent devices is generally less than 5%, which is still far behind the efficiency of phosphorescent devices. At present, fluorescent electroluminescent devices that can break through the 25% internal quantum efficiency limit mainly use the delayed fluorescence mechanism, which can effectively utilize the triplet excited state energy in the device. Delayed fluorescence mechanisms mainly include two categories: (1) TTA (Triplet-Triplet Annihilation) mechanism; (2) TADF (Thermally Activated Delayed Fluorescence) mechanism. The TTA mechanism is a mechanism that uses the fusion of two triplet excitons to generate singlet excitons, thereby increasing the singlet exciton generation rate. However, the maximum internal quantum efficiency of the device is only 40%-62.5%. The TADF mechanism is a mechanism that uses a small singlet-triplet energy level difference (ΔE ST ) is an organic small molecule material whose triplet excitons can be converted into singlet excitons under ambient thermal energy through the process of reverse intersystem crossing (RISC). Theoretically, the quantum efficiency of its device can reach 100%. However, the efficiency roll-off of its device is large at high brightness, which limits its application in full-color display and white light illumination. TADF molecules are mainly doped as guest materials in wide bandgap host materials to achieve high-efficiency thermally activated delayed fluorescence (see J.Am.Chem.Soc.2012,134,14706; Nature,2012,492,234; Mater.Horiz.,2014,1,264).

[0003] Unlike the localized state (LE) luminescence of traditional fluorescent molecules, TADF emission mainly originates from the transition of the intramolecular charge transfer (ICT) state. Since the structure of most TADF luminescent molecules adopts the form of electron donor (D: donor) group and electron acceptor (A; acceptor) group through conjugation or non-conjugation connection, that is, the so-called DA structure (structure 1), the electron donor group and the electron acceptor group are separated in space, and this type of molecule is defined as: separated DA structure. This DA-type structure is conducive to the spatial separation of the highest occupied molecular orbital (HOMO: the highest occupied molecular orbital) and the lowest unoccupied molecular orbital (LUMO: the lowest unoccupied molecular orbital) of the molecule, and thus it is easy to obtain TADF luminescence. Moreover, based on the DA-type structure, it is easy to achieve the regulation of the emission spectrum peak position (wavelength), that is, the luminescence color, because the structure of the electron donor and the electron acceptor and the relative ability to gain and lose electrons are easy to optimize. However, the DA structure shown in Structure 1 can easily lead to configuration and conformational changes in the molecule in the ground state and excited state, and produce a rich molecular vibration mode. Therefore, the emission spectrum of the TADF molecule based on the structure shown in Structure 1 is relatively wide, and the half-peak width of the emission spectrum of most of these luminescent molecules exceeds 100nm. Although the wider spectrum is beneficial for lighting applications, it cannot meet the requirements of high color purity in the display field. The main purpose of OLED luminescence is display, so the narrow spectrum design of TADF materials (i.e., smaller half-peak width) is very necessary.

[0004]

[0005] Structure 1. DA type molecular structure

[0006] In recent years, some luminescent compounds based on tri-coordinated B (boron) have been reported (see Angew. Chem. 2018, 130, 11486; J. Am. Chem. Soc., 2018, 140, 1195; Adv. Mater. 2016, 28, 2777; CN109155368A; WO2016 / 152544A1; WO2017 / 188111A1; WO2018 / 150832A1; WO2018 / 186374A1; WO2018 / 216990A1). The structural feature of these compounds is that the luminescent compounds contain at least one B atom coordinated with three benzene rings to form a very rigid chromophore core structure, and the three benzene rings coordinated with B are covalently connected to N. Such molecules are called BN complexes (Structure 2), that is, the compounds are luminescent compounds formed by the coordination of aromatic amine organic molecules with B.

[0007]

[0008] Structure 2. Based on the molecular model structure of the tri-coordinated BN complex.

[0009] The frontier molecular orbital of this type of tri-coordinate B complex has a characteristic, that is, the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) are distributed in the coordination system in an alternating manner (the so-called resonance structure), B is on the LUMO orbital, and N is on the HOMO orbital. Due to its unique HOMO and LUMO alternating layout electronic structure (resonance structure), this type of BN complex has excited state charge transfer and TADF luminescence properties (this type of molecule is defined as: resonance type DA molecule), and it is very important that its emission spectrum band is very narrow, the half-peak width of the emission spectrum can reach about 20nm, and the emission spectrum has very good color purity. Based on this type of compound, high-performance blue light or sky blue light (the peak of the luminescent light spectrum is between 450-490nm) organic electroluminescent devices can be prepared, and the electroluminescent spectrum is very narrow (half-peak width is about 25nm) and the color purity is very high. However, it is very difficult to design and synthesize green and red light materials with narrow emission spectra based on this resonant BN structure. The main reason is that although molecules with emission peaks in the green or even red region can be obtained by increasing the degree of conjugation of aromatic amines, the expansion of the conjugated system will destroy the electronic structure of the alternating layout of HOMO and LUMO, and will also lead to a significant increase in the vibration modes of the conjugated system, which will increase the chance of coupling between the excited state electronic transition energy level and the molecular vibration energy level, thus causing the emission spectrum to become wider, and it is impossible to obtain green and red narrow spectrum emission materials with ideal color purity.

[0010] In order to overcome the interference of light emitted under sunlight (especially when the sunlight is strong) on ​​the display effect, the organic electroluminescent display screen (OLED display screen) based on organic electroluminescent diodes needs to add a polarizing optical film on the surface of the OLED display screen, which is used to eliminate the light reflection effect on the surface of the display screen. However, when the natural light emitted by the OLED display screen is eliminated by 50% after passing through the polarizing optical film, the power consumption of the OLED display screen will increase significantly, and the life span will be significantly reduced. If the light emitted by the OLED display screen is not natural light but ideal circularly polarized light, the light emitted by the OLED display screen itself will not be partially eliminated after passing through the polarizing optical film. In principle, it can be 100% transmitted through the polarizing optical film for information display.

[0011] Therefore, it is of great significance to develop new luminescent materials that have narrow spectral emission characteristics and can emit circularly polarized light and their application in organic electroluminescent devices. Summary of the invention

[0012] The technical problem to be solved by the present invention is to overcome the defects of the existing separation type DA structure and resonance type DA structure compounds, such as wide emission spectrum, inability to obtain green light and red light narrow spectrum with ideal color purity, and provide a boron nitrogen compound, its composition and organic electroluminescent device. The boron nitrogen compound of the present invention emits light in the green to red light region and has a narrow spectrum luminescence characteristic, and can also effectively adjust the emission wavelength to achieve fine control of the emission wavelength range of 493-613nm.

[0013] The present invention provides a boron nitrogen compound as shown in Formula I:

[0014]

[0015] Among them, R 1 and R 2 are independently H, D (deuterium), halogen, C1-C 20 Alkyl, with one or more R a Substituted C1-C 20 Alkyl, -O-C1-C 20 Alkyl, with one or more R b Substituted-O-C1-C 20 Alkyl, C3-C 10 Cycloalkyl, with one or more R c Substituted C3-C 10 Cycloalkyl, C6-C 14 Aryl, one or more R d Substituted C6-C 14 Aryl, 5-18 membered heteroaryl, substituted by one or more R e Substituted 5-18 membered heteroaryl or -NR 3 R 4 , the 5-18 membered heteroaryl and one or more R e The heteroatoms in the substituted 5-18 membered heteroaryl group are independently one or more of N, S and O, and the number of the heteroatoms is 1, 2 or 3;

[0016] R a D (deuterium), halogen, CN, -O-C1-C 12 Alkyl, C2-C6 alkenyl, C3-C 10 Cycloalkyl, C6-C 14 Aryl, one or more R a-1 Substituted C6-C 14Aryl, 5-18 membered heteroaryl, substituted by one or more R a-2 Substituted 5-18 membered heteroaryl or -NR 5 R 6 , the 5-18 membered heteroaryl and one or more R a-2 The heteroatoms in the substituted 5-18 membered heteroaryl group are independently one or more of N, S and O, and the number of the heteroatoms is 1, 2 or 3;

[0017] R b , R c , R d and R e are independently D (deuterium), halogen, CN, C1-C 12 Alkyl, C1-C 12 Alkyl, C2-C6 alkenyl, -O-C1-C 12 Alkyl, C3-C 10 Cycloalkyl, C6-C 14 Aryl, one or more R a-3 Substituted C6-C 14 Aryl, 5-18 membered heteroaryl, substituted by one or more R a-4 Substituted 5-18 membered heteroaryl or -NR 7 R 8 , the 5-18 membered heteroaryl and one or more R a-4 The heteroatoms in the substituted 5-18 membered heteroaryl group are independently one or more of N, S and O, and the number of the heteroatoms is 1, 2 or 3;

[0018] R a-1 , R a-2 , R a-3 and R a-4 are independently D (deuterium), halogen, CN, C1-C 12 Alkyl, -O-C1-C 12 Alkyl, C3-C 10 Cycloalkyl, C6-C 14 Aryl, 5-18 membered heteroaryl or diphenylamino, wherein the heteroatoms in the 5-18 membered heteroaryl are one or more of N, S and O, and the number of heteroatoms is 1, 2 or 3;

[0019] R 3 , R 4 , R 5 , R 6 , R 7 and R 8 Independently C6-C 14 Aryl or one or more R f Substituted C6-C 14 Aryl,

[0020] Or, R 3 and R 4 , R 5 and R 6 , or, R 7 and R 8 The nitrogen atom to which it is attached independently forms a 5-18 membered heteroaryl group or is replaced by one or more R g substituted 5-18 membered heteroaryl,

[0021] The 5-18 membered heteroaryl group and one or more R g The heteroatoms in the substituted 5-18 membered heteroaryl group are independently one or more of N, S and O, and the number of the heteroatoms is 1, 2 or 3;

[0022] R f and R g are independently D (deuterium), halogen, CN, C1-C 12 Alkyl, -O-C1-C 12 Alkyl, C3-C 10 Cycloalkyl, C6-C 14 Aryl, 5-18 membered heteroaryl or diphenylamino, wherein the heteroatoms in the 5-18 membered heteroaryl are one or more of N, S and O, and the number of heteroatoms is 1, 2 or 3;

[0023] R n for

[0024] is the chiral axis, indicating S or R configuration;

[0025] R n1 , R n2 , R n3 and R n4 are independently H, D (deuterium), cyano, C1-C8 alkyl, -O-C1-C8 alkyl, C3-C 10 Cycloalkyl or C6-C 14 Aryl, and "R n1 , R n2 and R n3 ” or “R n1 , R n2 and R n4 " at least one of which is a cyano group;

[0026] R n5 and R n6 , or, R n7 and R n8 The carbon atoms to which it is attached independently form a 5-6 membered cycloalkyl group, which is supported by one or more R n5-1 Substituted 5-6 membered cycloalkyl, C6-C 14Aryl or 1 or more R n5-2 Substituted C6-C 14 Aryl;

[0027] R n5-1 and R n5-2 are independently H, D (deuterium), halogen, C1-C 20 Alkyl, -O-C1-C 20 Alkyl, C3-C 10 Cycloalkyl, C6-C 24 Aryl or 5-18 membered heteroaryl, wherein the heteroatoms in the 5-18 membered heteroaryl are independently one or more of N, S and O, and the number of the heteroatoms is 1, 2 or 3.

[0028] In a preferred embodiment of the present invention, in the above-mentioned boron nitrogen compound as shown in Formula I, certain groups have the following definitions, and the definitions of the unmentioned groups are as described in any scheme, hereinafter referred to as: in a preferred embodiment of the present invention.

[0029] In a preferred embodiment of the present invention,

[0030] R 1 are independently H, C1-C 20 Alkyl, -O-C1-C 20 Alkyl, C3-C 10 Cycloalkyl, C6-C 14 Aryl, one or more R d Substituted C6-C 14 Aryl or -NR 3 R 4 ;

[0031] R d C1-C 12 Alkyl or -O-C1-C 12 alkyl;

[0032] R 3 and R 4 Independently C6-C 14 Aryl or one or more R f Substituted C6-C 14 Aryl;

[0033] Or, R 3 and R 4 Together with the nitrogen atom to which it is attached, it forms a 5-18 membered heteroaryl group or is replaced by one or more R g substituted 5-18 membered heteroaryl;

[0034] R f Independently C1-C 12 Alkyl or -O-C1-C 12 alkyl;

[0035] R g Independently C1-C 12 alkyl;

[0036] R n for

[0037] “R n1 , R n2 and R n3 ” or “R n1 , R n2 and R n4 "One of them is cyano and the other two are hydrogen;

[0038] R n5 and R n6 , or, R n7 and R n8 The carbon atoms to which it is attached independently form a 5-6 membered cycloalkyl or a C6-C 14 Aryl.

[0039] In a preferred embodiment of the present invention,

[0040] R 1 are independently H, C1-C 20 Alkyl, C6-C 14 Aryl, one or more R d Substituted C6-C 14 Aryl or -NR 3 R 4 ;

[0041] R d Independently C1-C 12 alkyl;

[0042] R 3 and R 4 Independently C6-C 14 Aryl or one or more R f Substituted C6-C 14 Aryl;

[0043] Or, R 3 and R 4 Together with the nitrogen atom to which it is attached, it forms a 5-18 membered heteroaryl group or is replaced by one or more R g substituted 5-18 membered heteroaryl;

[0044] R f and R g Independently C1-C 12 alkyl;

[0045] R n for

[0046] “R n1 , R n2 and R n3 ” or “R n1 , R n2 and R n4 "One of them is cyano and the other two are hydrogen;

[0047] R n5 and R n6 , or, R n7 and R n8 The carbon atoms to which it is attached independently form a 5-6 membered cycloalkyl or a C6-C 14 Aryl.

[0048] In a preferred embodiment of the present invention,

[0049] R 1 are independently H, C1-C 20 Alkyl, C6-C 14 Aryl or one or more R d Substituted C6-C 14 Aryl;

[0050] R d Independently C1-C 12 alkyl;

[0051] R 3 and R 4 Independently C6-C 14 Aryl or one or more R f Substituted C6-C 14 Aryl;

[0052] Or, R 3 and R 4 Together with the nitrogen atom to which it is attached, it forms a 5-18 membered heteroaryl group or is replaced by one or more R g substituted 5-18 membered heteroaryl;

[0053] R f and R g Independently C1-C 12 alkyl;

[0054] R n for

[0055] “R n1 , R n2 and R n3 ” or “R n1 , R n2 and R n4"One of them is cyano and the other two are hydrogen;

[0056] R n5 and R n6 , or, R n7 and R n8 The carbon atoms to which it is attached independently form a 5-6 membered cycloalkyl or a C6-C 14 Aryl.

[0057] In a preferred embodiment of the present invention, R 1 are independently H, C1-C 20 Alkyl, -O-C1-C 20 Alkyl, C3-C 10 Cycloalkyl, C6-C 14 Aryl, one or more R d Substituted C6-C 14 Aryl or -NR 3 R 4 ;

[0058] Preferably H, C1-C 20 Alkyl, C6-C 14 Aryl, one or more R d Substituted C6-C 14 Aryl or -NR 3 R 4 ;

[0059] More preferably C1-C 20 Alkyl, C6-C 14 Aryl or one or more R d Substituted C6-C 14 Aryl.

[0060] In a preferred embodiment of the present invention, R 2 Independently C1-C 20 Alkyl, -O-C1-C 20 Alkyl, C3-C 10 Cycloalkyl, C6-C 14 Aryl, one or more R d Substituted C6-C 14 Aryl or -NR 3 R 4 ;

[0061] Preferably C1-C 20 Alkyl, C6-C 14 Aryl, one or more R d Substituted C6-C 14 Aryl or -NR 3 R 4 ;

[0062] More preferably C1-C 20 Alkyl, C6-C 14 Aryl, one or more R d Substituted C6-C 14 Aryl.

[0063] In a preferred embodiment of the present invention, R d Independently C1-C 12 alkyl.

[0064] In a preferred embodiment of the present invention, R 3 and R 4 , or, R 5 and R 6 Together with the nitrogen atom to which it is attached, it forms a 5-18 membered heteroaryl group or is replaced by one or more R g substituted 5-18 membered heteroaryl;

[0065] Preferably, R 3 and R 4 , or, R 5 and R 6 Together with the nitrogen atom to which it is attached, it independently forms a g Substituted 5-18 membered heteroaryl.

[0066] In a preferred embodiment of the present invention, R n for

[0067] R n1 , R n2 , R n3 and R n4 are independently H or cyano, and "R n1 , R n2 and R n3 ” or “R n1 , R n2 and R n4 ", at least one of which is a cyano group;

[0068] Preferably R n1 and R n2 For H, R n3 It is cyano.

[0069] In a preferred embodiment of the present invention, R n5 and R n6 , or, R n7 and R n8 The carbon atoms to which it is attached independently form a 5-6 membered cycloalkyl or a C6-C 14 Aryl;

[0070] Preferably, R n5 and Rn6 , or, R n7 and R n8 Together with the carbon atom to which it is attached, it independently forms a 5-6 membered cycloalkyl group.

[0071] In a preferred embodiment of the present invention, when R 1 , R 2 , R a , R b , R c , R d , R e , R a-1 , R a-2 , R a-3 and R a-4 When independently halogen, the halogen is F, Cl, Br or I.

[0072] In a preferred embodiment of the present invention, when R 1 and R 2 Independently C1-C 20 Alkyl, with one or more R a Substituted C1-C 20 Alkyl, -O-C1-C 20 Alkyl, with one or more R b Substituted-O-C1-C 20 When alkyl, the C1-C 20 Alkyl, said one or more R a Substituted C1-C 20 Alkyl, the -O-C1-C 20 The alkyl group and the one or more R b Substituted-O-C1-C 20 C1-C 20 The alkyl groups are independently C1-C 10 Alkyl (e.g., methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-hexyl, n-octyl, n-decyl or ), preferably a C1-C4 alkyl group (e.g., methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl).

[0073] In a preferred embodiment of the present invention, when R 1 and R 2 Independently for C3-C 10 Cycloalkyl or one or more R c Substituted C3-C 10 When the cycloalkyl group is 10 The cycloalkyl group and the c Substituted C3-C 10C3-C in cycloalkyl 10 The cycloalkyl group is independently a C3-C6 monocyclic cycloalkyl group (e.g., cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl) or a C7-C 10 Tricyclic cycloalkyl (eg, adamantyl).

[0074] In a preferred embodiment of the present invention, when R 1 and R 2 Independently C6-C 14 Aryl or one or more R d Substituted C6-C 14 In the case of an aryl group, the C6-C 14 Aryl or said one or more R d Substituted C6-C 14 C6-C in aromatic groups 14 Aryl is independently phenyl, naphthyl, anthracenyl or phenanthrenyl.

[0075] In a preferred embodiment of the present invention, when R 1 and R 2 Independently for one or more R d Substituted C6-C 14 When the group is aryl, the R d The number of is 1, 2 or 3.

[0076] In a preferred embodiment of the present invention, when R 1 and R 2 is independently a 5-18 membered heteroaryl or is replaced by one or more R e When the 5-18 membered heteroaryl is substituted, the 5-18 membered heteroaryl and the substituted by one or more R e The 5- to 18-membered heteroaryl in the substituted 5- to 18-membered heteroaryl is independently a 5- to 6-membered heteroaryl.

[0077] In a preferred embodiment of the present invention, when R a O-C1-C 12 When the -O-C1-C 12 The alkyl group is -O-C1-C6 alkyl.

[0078] In a preferred embodiment of the present invention, when R a C3-C 10 When the cycloalkyl group is 10 The cycloalkyl group is a C3-C6 monocyclic cycloalkyl group or a C7-C 10 Tricyclic cycloalkyl.

[0079] In a preferred embodiment of the present invention, when R a is a 5-18 membered heteroaryl or is replaced by one or more R a-2When the 5-18 membered heteroaryl is substituted, the 5-18 membered heteroaryl and the substituted by one or more R a-2 The 5- to 18-membered heteroaryl in the substituted 5- to 18-membered heteroaryl is independently a 5- to 6-membered heteroaryl.

[0080] In a preferred embodiment of the present invention, when R b , R c , R d and R e Independently C1-C 12 Alkyl, C1-C 12 Alkyl or -O-C1-C 12 When the C1-C 12 Alkyl, the C1-C 12 The alkyl group and the -O-C1-C 12 C1-C 12 The alkyl group is independently a C1-C6 alkyl group (eg, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl or n-hexyl).

[0081] In a preferred embodiment of the present invention, when R b , R c , R d and R e Independently for C3-C 10 When the cycloalkyl group is 10 The cycloalkyl group is a C3-C6 monocyclic cycloalkyl group (e.g., cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl) or a C7-C 10 Tricyclic cycloalkyl (eg, adamantyl).

[0082] In a preferred embodiment of the present invention, when R b , R c , R d and R e Independently C6-C 14 Aryl or one or more R a-3 Substituted C6-C 14 In the case of an aryl group, the C6-C 14 The aryl group and the one or more R a-3 Substituted C6-C 14 C6-C in aromatic groups 14 Aryl is independently phenyl, naphthyl, anthracenyl or phenanthrenyl.

[0083] In a preferred embodiment of the present invention, when R b , R c , R d and R eis independently a 5-18 membered heteroaryl or is replaced by one or more R a-4 When the 5-18 membered heteroaryl is substituted, the 5-18 membered heteroaryl and the substituted by one or more R a-4 The 5- to 18-membered heteroaryl in the substituted 5- to 18-membered heteroaryl is independently a 5- to 6-membered heteroaryl.

[0084] In a preferred embodiment of the present invention, when R a-1 , R a-2 , R a-3 and R a-4 Independently C1-C 12 Alkyl or -O-C1-C 12 When alkyl, the C1-C 12 The alkyl group and the -O-C1-C 12 C1-C 12 The alkyl group is independently a C1-C6 alkyl group.

[0085] In a preferred embodiment of the present invention, when R a-1 , R a-2 , R a-3 and R a-4 Independently for C3-C 10 When the cycloalkyl group is 10 The cycloalkyl group is independently a C3-C6 cycloalkyl group.

[0086] In a preferred embodiment of the present invention, when R a-1 , R a-2 , R a-3 and R a-4 Independently C6-C 14 In the case of an aryl group, the C6-C 14 Aryl is independently phenyl, naphthyl, anthracenyl or phenanthrenyl.

[0087] In a preferred embodiment of the present invention, when R a-1 , R a-2 , R a-3 and R a-4 When independently a 5- to 18-membered heteroaryl group, the 5- to 18-membered heteroaryl group is independently a 5- to 6-membered heteroaryl group.

[0088] In a preferred embodiment of the present invention, when R 3 , R 4 , R 5 , R 6 , R 7 and R 8 Independently C6-C 14 Aryl or one or more R f Substituted C6-C 14In the case of an aryl group, the C6-C 14 Aryl is independently phenyl, naphthyl, anthracenyl or phenanthrenyl, for example phenyl.

[0089] In a preferred embodiment of the present invention, when R 3 and R 4 , or, R 5 and R 6 The nitrogen atom to which it is attached independently forms a 5-18 membered heteroaryl group or is replaced by one or more R g When the 5-18 membered heteroaryl is substituted, the 5-18 membered heteroaryl and the substituted by one or more R g The 5-18-membered heteroaryl in the substituted 5-18-membered heteroaryl is independently a 5-13-membered heteroaryl, the heteroatom is N, and the number is 1, for example

[0090] In a preferred embodiment of the present invention, when R f and R g Independently C1-C 12 Alkyl or -O-C1-C 12 When the C1-C 12 The alkyl group and the -O-C1-C 12 C1-C 12 The alkyl groups are independently C1-C8 alkyl groups (e.g., methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-hexyl or ), preferably a C1-C4 alkyl group (e.g., methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl).

[0091] In a preferred embodiment of the present invention, when R n5 and R n6 , or, R n7 and R n8 Together with the carbon atom it is connected to, it independently forms a C6-C 14 Aryl or 1 or more R n5-2 Substituted C6-C 14 In the case of an aryl group, the C6-C 14 The aryl group and the n5-2 Substituted C6-C 14 C6-C in aromatic groups 14 Aryl is independently phenyl, naphthyl, anthracenyl or phenanthrenyl, for example phenyl.

[0092] In a preferred embodiment of the present invention, when R 1 and R 2 Independently for one or more R d Substituted C6-C 14When the group is aryl, the group is represented by one or more R d Substituted C6-C 14 The aryl groups are independently

[0093]

[0094] In a preferred embodiment of the present invention, when R 3 and R 4 Independently for one or more R f Substituted C6-C 14 When the group is aryl, the group is represented by one or more R f Substituted C6-C 14 The aryl groups are independently

[0095] In a preferred embodiment of the present invention, when R 3 and R 4 Together with the nitrogen atom to which it is attached, it forms a g When the 5-18 membered heteroaryl is substituted, the g The substituted 5-18 membered heteroaryl is

[0096] In a preferred embodiment of the present invention, Any of the following groups:

[0097]

[0098]

[0099]

[0100]

[0101]

[0102] In the above structure, -C4H9 is n-butyl, -C6H 13 is n-hexyl, -C8H 17 is n-octyl, -C 10 H 21 is n-decyl, -C 12 H 25 In a preferred embodiment of the present invention, R nfor (R / S represents S or R configuration, the same below).

[0103] In a preferred embodiment of the present invention, the boron nitrogen compound as shown in formula I is any of the following compounds:

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126] Among them, -C4H9 in the structural formula is n-butyl, -C6H13 is n-hexyl, -C8H 17 is n-octyl, -C 10 H 21 is n-decyl, -C 12 H 25 It is n-dodecyl.

[0127] The present invention also provides a method for preparing the boron nitrogen compound as shown in formula I, which comprises the following steps: subjecting a compound as shown in formula II and a compound as shown in formula III to Suzuki reaction in a solvent under the action of an alkaline reagent and a catalyst to obtain the boron nitrogen compound as shown in formula I;

[0128]

[0129] Where X is a halogen, R 1 , R 2 and R n The definitions are the same as those in any of the embodiments of the present invention.

[0130] The conditions and operation of the Suzuki reaction can be conventional conditions and operation of such reactions in the art, and the present invention particularly prefers the following conditions:

[0131] The alkaline agent is, for example, potassium carbonate.

[0132] The catalyst is, for example, tetrakis(triphenylphosphine)palladium.

[0133] The solvent is, for example, tetrahydrofuran and water (the volume ratio of tetrahydrofuran to water is, for example, 8:1).

[0134] The present invention also provides a compound II:

[0135]

[0136] Among them, R 1 and R 2 The definitions are the same as those described in any scheme of the present invention.

[0137] The compound II is preferably the following compound:

[0138]

[0139] The present invention also provides a compound III:

[0140]

[0141] Where X is a halogen, R n1 , R n2 , R n3 , R n4 , Rn5 , R n6 , R n7 , R n8 and The definitions are the same as above.

[0142] The compound III is preferably the following compound:

[0143]

[0144] For example

[0145] Herein, "R / S" indicates that the compound is an R-configuration compound or an S-configuration compound.

[0146] The present invention also provides an organic electroluminescent composition, which comprises the boron nitrogen compound shown in Formula I and a host material.

[0147] In a preferred embodiment of the present invention, in the organic electroluminescent composition, the boron nitrogen compound as shown in formula I is 0.3-30.0 parts by weight, such as 0.3 parts; the host material is 99.7-70.0 parts by weight, such as 99.7 parts.

[0148] The host material has electron and / or hole transport capability and the triplet excited state energy is higher than or close to the triplet excited state energy of the boron nitrogen compound shown in Formula I.

[0149] In a preferred embodiment of the present invention, in the organic electroluminescent composition, the host material is a carbazole derivative host material and / or a carboline derivative host material.

[0150] In a preferred embodiment of the present invention, the molecular structure of the carbazole derivative main material or the carbazole derivative main material is as shown in the following general formula H-1, H-2, H-3, H-4, H-5, H-6 or H-7:

[0151]

[0152] wherein X1, Y1 and Z1 are independently CH or N, and at most one of X1, Y1 and Z1 is N;

[0153] R 1H and R 2H Independently any of the following groups:

[0154]

[0155]

[0156] wherein X2, Y2 and Z2 are independently CH or N, and at most one of X2, Y2 and Z2 is N;

[0157] R aH and R bH are independently H, C1-C 20 Alkyl, -O-C1-C 20 Alkyl, C6-C 20 Aryl, C1-C 20 Alkyl-substituted C6-C 20 Aryl or -O-C1-C 20 Alkyl-substituted C6-C 20 Aryl.

[0158] In a preferred embodiment of the present invention, certain groups in the main material of the carbazole derivative or the main material of the carbazole derivative as shown in formula H-1, H-2, H-3, H-4, H-5, H-6 or H-7 are defined as follows, and the unmentioned groups are the same as those described in any scheme of the present invention, hereinafter referred to as "a preferred embodiment of the present invention".

[0159] In a preferred embodiment of the present invention, R aH and R bH are independently H, C1-C 20 Alkyl, C6-C 20 Aryl or C1-C 20 Alkyl-substituted C6-C 20 Aryl.

[0160] In a preferred embodiment of the present invention, when R aH and R bH Independently C1-C 20 Alkyl, -O-C1-C 20 Alkyl, C1-C 20 Alkyl-substituted C6-C 20 Aryl or -O-C1-C 20 Alkyl-substituted C6-C 20 In the case of an aryl group, the C1-C 20 Alkyl, the -O-C1-C 20 Alkyl, the C1-C 20 Alkyl-substituted C6-C 20 Aryl and the -O-C1-C 20 Alkyl-substituted C6-C 20 C1-C in aromatic groups 20 The alkyl groups are independently C1-C 12 Alkyl groups, e.g. Methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-hexyl or n-dodecyl.

[0161] In a preferred embodiment of the present invention, when R aH and R bH Independently C6-C 20 Aryl, C1-C 20 Alkyl-substituted C6-C 20 Aryl or -O-C1-C 20 Alkyl-substituted C6-C 20 In the case of an aryl group, the C6-C 20 Aryl, the C1-C 20 Alkyl-substituted C6-C 20 Aryl and the -O-C1-C 20 Alkyl-substituted C6-C 20 C6-C in aromatic groups 20 Arylalkyl is independently C6-C 14 Aryl, for example phenyl, naphthyl, phenanthrenyl or anthracenyl.

[0162] In a preferred embodiment of the present invention, when R aH and R bH Independently C1-C 20 Alkyl-substituted C6-C 20 When aryl or -, the C1-C 20 Alkyl-substituted C6-C 20 The aryl groups are independently

[0163] In a preferred embodiment of the present invention, the main material of the carbazole derivative or the main material of the carbazole derivative as shown in formula H-1, H-2, H-3, H-4, H-5, H-6 or H-7 is any of the following structures:

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184] Among them, -C4H9 in the structural formula is n-butyl, -C6H 13 is n-hexyl, -C 12 H 25 It is n-dodecyl.

[0185] In a preferred embodiment of the present invention, the molecular structure of the host material of the organic electroluminescent composition is a carbazole derivative host material or a carbazole derivative host material as shown in the following general formula H-1 or H-5.

[0186] In a preferred embodiment of the present invention, in the organic electroluminescent composition, the main material is 99.7-70.0 parts by weight, and the main material is one or two compounds of the carbazole derivative main material or the carbazole derivative main material as shown in formula H-1 to H-7; when the main material contains two compounds, the weight ratio thereof is 1:5-5:1.

[0187] In one embodiment of the present invention, in the organic electroluminescent composition, the host material is 99.7-70.0 parts by weight, and the host material is one or two compounds of formula H-1 to H1-427. When the host material contains two compounds, the weight ratio is 1:5-5:1.

[0188] In one embodiment of the present invention, the organic electroluminescent composition comprises 0.3-30.0 parts by weight of any one of the compounds of formulas BN-1R to BN-400R and BN-1S to BN-400S and 70-99.7 parts by weight of one or two of the compounds of formulas H-1 to H1-427.

[0189] In a preferred embodiment of the present invention, the organic electroluminescent composition is composed of 3 parts by weight of the boron nitrogen compound represented by formula I and 97 parts by weight of a carbazole derivative host material and / or a carbazole derivative host material.

[0190] In a preferred embodiment of the present invention, the organic electroluminescent composition is composed of 3 parts by weight of the boron nitrogen compound shown in formula I and 97 parts by weight of a host material; the molecular structure of the host material is a carbazole derivative host material or a carbazole derivative host material shown in the following general formula H-1 or H-5.

[0191] In a preferred embodiment of the present invention, the organic electroluminescent composition is composed of 3 parts by weight of the boron nitrogen compound shown in formula I and 97 parts by weight of a host material, wherein the host material is

[0192] In a preferred embodiment of the present invention, the organic electroluminescent composition is composed of 3 parts by weight ("R" indicates an R-configuration compound) and 97 parts by weight composition.

[0193] In a preferred embodiment of the present invention, the organic electroluminescent composition is composed of 3 parts by weight ("R" indicates an R-configuration compound) and 97 parts by weight composition.

[0194] In a preferred embodiment of the present invention, the organic electroluminescent composition is composed of 3 parts by weight ("S" indicates an S-configuration compound) and 97 parts by weight composition.

[0195] In a preferred embodiment of the present invention, the organic electroluminescent composition is composed of 3 parts by weight ("S" indicates an S-configuration compound) and 97 parts by weight composition.

[0196] In a preferred embodiment of the present invention, in the organic electroluminescent composition, the host material further comprises a 1,3,5-triazine derivative host material. When the host material further comprises a 1,3,5-triazine derivative host material, the weight ratio of the 1,3,5-triazine derivative host material to the carbazole derivative host material and / or the carbazole derivative host material is 1:5-5:1, for example 2:1.

[0197] The 1,3,5-triazine derivative can be a conventional triazine main material in the art. In a preferred embodiment of the present invention, the molecular structure of the 1,3,5-triazine derivative main material is as shown in the following general formula Trz1-A, Trz2-A, Trz3-A or Trz4-A:

[0198]

[0199] R 1a , R 1b , R 2a , R 2b , R 3a and R 3b One or two of them are R Tz ;

[0200] R 1a , R 1b , R 2a , R 2b , R 3a and R 3b wherein the rest are independently hydrogen, deuterium, C1-C8 alkyl, -O-C1-C8 alkyl, C6-C 18 Aryl, C1-C8 alkyl substituted C6-C 18 Aryl, -O-C1-C8 alkyl substituted C6-C 18 C6-C 18 The aromatic group;

[0201] R Tz Independently any one of the groups Tz-n (n=1-61) shown below:

[0202]

[0203]

[0204]

[0205] In a preferred embodiment of the present invention, certain groups in the compounds shown in the following formulae Trz1-A, Trz2-A, Trz3-A or Trz4-A are defined as follows, and the unmentioned groups are the same as those described in any scheme of the present invention, hereinafter referred to as "a preferred embodiment of the present invention".

[0206] In a preferred embodiment of the present invention, R 1a , R 1b , R 2a , R 2b , R 3a and R 3b One or two of them are independently RTz;

[0207] R 1a , R 1b , R 2a , R 2b , R 3a and R 3b The rest are independently hydrogen, C6-C 18 Aryl or cyano substituted C6-C 18 Aryl.

[0208] In a preferred embodiment of the present invention, when R 1a , R 1b , R 2a , R 2b , R 3a and R 3b The rest are independently C6-C 18 Aryl, C1-C8 alkyl substituted C6-C 18 Aryl, -O-C1-C8 alkyl substituted C6-C 18 C6-C 18 When the C6-C 18 Aryl, C1-C8 alkyl substituted C6-C 18 Aryl, the -O-C1-C8 alkyl substituted C6-C 18 The aryl group and the cyano-substituted C6-C 18 The C6-C 18 The aryl group of is phenyl, naphthyl, phenanthrenyl or anthracenyl, for example phenyl.

[0209] In a preferred embodiment of the present invention, the main material of the 1,3,5-triazine derivative is any of the following compounds:

[0210]

[0211]

[0212]

[0213]

[0214] In a preferred embodiment of the present invention, the molecular structure of the 1,3,5-triazine derivative main material is as shown in Formula Trz1-A.

[0215] In one embodiment of the present invention, in the organic electroluminescent composition, the host material is any one of the 1,3,5-triazine derivative host materials shown in formula Trz1-A, Trz2-A, Trz3-A or Trz4-A, and any one of the compounds shown in formula H-1 to H-7. When the host material is any one of the 1,3,5-triazine derivatives shown in formula Trz1-A, Trz2-A, Trz3-A or Trz4-A, and any one of the compounds shown in formula H-1 to H-7, the weight ratio is 1:5-5:1. For example, 2:1.

[0216] In a preferred embodiment of the present invention, in the organic electroluminescent composition, the main material is the above-mentioned 1,3,5-triazine derivative main material as shown in formula TRZ-1-A, and the above-mentioned carbazole derivative main material or carbazole derivative main material as shown in formula H-1 or H-5.

[0217] In a certain embodiment of the present invention, the organic electroluminescent composition comprises 0.3-30.0 parts by weight of the boron nitrogen compound as shown in formula I and 70-99.7 parts by weight of a host material; the host material is any one of the 1,3,5-triazine derivative host materials as shown in formula Trz1-A, Trz2-A, Trz3-A or Trz4-A, and any one of the carbazole derivative host materials or carboline derivative host materials as shown in formula H-1 to H-7. When the host material is any one of the 1,3,5-triazine derivative host materials as shown in formula Trz1-A, Trz2-A, Trz3-A or Trz4-A, and any one of the carbazole derivative host materials or carboline derivative host materials as shown in formula H-1 to H-7, the weight ratio is 1:5-5:1.

[0218] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the boron nitrogen compounds shown in Formula I (content is 0.3wt-30.0wt%); the main material (content is 99.7wt-70.0wt%) is composed of any one of the 1,3,5-triazine derivatives shown in Formulas TRZ-1 to TRZ-56 and any one of the carbazole or carboline derivatives shown in Formulas H1-1 to H1-427. For example, in the main material, the weight ratio between the 1,3,5-triazine derivative and the carbazole or carboline derivative is 1:5 to 5:1.

[0219] In one embodiment of the present invention, the organic electroluminescent composition comprises 0.3-30.0 parts by weight of any one of the boron nitrogen compounds shown in Formula I and 70-99.7 parts by weight of a host material; the host material is any one of the 1,3,5-triazine derivative host materials shown in Formulas TRZ-1 to TRZ-56, and any one of the carbazole derivative host materials or carboline derivative host materials shown in Formulas H1-1 to H1-427. When the host material is any one of the 1,3,5-triazine derivative host materials shown in Formulas TRZ-1 to TRZ-56, and any one of the carbazole derivative host materials or carboline derivative host materials shown in Formulas H1-1 to H1-427, the weight ratio is 1:5-5:1, for example, 2:1.

[0220] In one embodiment of the present invention, the organic electroluminescent composition comprises 0.3-30.0 parts by weight of any one of the compounds of formulas BN-1R to BN-400R and BN-1S to BN-400S and 70-99.7 parts by weight of a host material; the host material is any one of the 1,3,5-triazine derivative host materials shown in formulas TRZ-1 to TRZ-56, and any one of the carbazole derivative host materials or carboline derivative host materials shown in formulas H1-1 to H1-427. When the host material is any one of the 1,3,5-triazine derivative host materials shown in formulas TRZ-1 to TRZ-56, and any one of the carbazole derivative host materials or carboline derivative host materials shown in formulas H1-1 to H1-427, the weight ratio is 1:5-5:1, for example, 2:1.

[0221] In a preferred embodiment of the present invention, the organic electroluminescent composition is composed of 3 parts by weight of the boron nitrogen compound as shown in formula I and 97 parts by weight of a host material; the host material is a carbazole derivative host material or a carboline derivative host material as shown in formula H-5, and a 1,3,5-triazine derivative host material as shown in formula TRZ-A. When the host material is any one of the 1,3,5-triazine derivative host materials as shown in formula TRZ-A, and any one of the carbazole derivative host materials or carboline derivative host materials as shown in formula H-5, the weight ratio is 1:5-5:1, for example, 2:1.

[0222] In a preferred embodiment of the present invention, the organic electroluminescent composition is composed of 3 parts of the boron nitrogen compound shown in Formula I and 97 parts of a host material; the host material is in a weight ratio of 1:2

[0223] The present invention also provides a use of the boron nitrogen compound as shown in formula I or the organic electroluminescent composition as an organic electroluminescent material.

[0224] In a preferred embodiment of the present invention, the boron nitrogen compound as shown in Formula I can be used as a doped light-emitting material.

[0225] In a preferred embodiment of the present invention, the organic electroluminescent composition can be used as a light-emitting layer preferably used to prepare an organic electroluminescent device.

[0226] The present invention also provides an organic electroluminescent device, which comprises an anode, a light-emitting layer, an optional hole injection layer, an optional hole transport layer, an optional electron transport layer, an optional electron injection layer and a cathode; wherein at least one of the light-emitting layer, the electron injection layer, the electron transport layer, the hole transport layer and the hole injection layer comprises the above-mentioned organic electroluminescent composition.

[0227] In a preferred embodiment of the present invention, the light-emitting layer of the organic electroluminescent device comprises the above-mentioned organic electroluminescent composition.

[0228] In a preferred embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer, and the light-emitting principle of the light-emitting layer is based on energy transfer from the host material to the boron nitrogen compound described in Formula I or carrier capture of the light-emitting material itself.

[0229] In a preferred embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the main material in the organic electroluminescent composition is the above-mentioned carbazole derivative and / or carbazole derivative main material, and the carbazole derivative and / or carbazole derivative is as shown in formula H-1 to H-7 (for example, containing 0.3-30.0wt% of any one of the boron nitrogen compounds shown in formula I, and the remaining 99.7-70.0wt% of the main material is composed of 1-2 compounds of formula H-1 to H-7. When the main body contains 2 compounds of formula H-1 to H-7, the weight ratio of the two compounds is 1:5 to 5:1).

[0230] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer, and the main material in the composition is 1-2 of compounds H1-1 to H1-427 (for example, when the composition contains 2 compounds of formulas H1-1 to H1-427, the weight ratio of the two compounds is 1:5 to 5:1).

[0231] In a certain embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the boron nitrogen compounds shown in Formula I (content is 0.3wt-30.0wt%); the main material (content is 99.7wt-70.0wt%) is composed of any one of the 1,3,5-triazine derivatives shown in Formula Trz1-A, Trz2-A, Trz3-A or Trz4-A and any one of the compounds shown in Formula H-1 to H-7. For example, in the main material, the weight ratio between the 1,3,5-triazine derivative shown in Trz1-A, Trz2-A, Trz3-A or Trz4-A and the compound shown in H-1, H-2, H-3, H-4, H-5, H-6 or H-7 is 1:5 to 5:1.

[0232] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the boron nitrogen compounds shown in Formula I (content is 0.3wt-30.0wt%); the main material (content is 99.7wt-70.0wt%) is composed of any one of the 1,3,5-triazine derivatives shown in Formulas TRZ-1 to TRZ-56 and any one of the carbazole or carboline derivatives shown in Formulas H1-1 to H1-427. For example, in the main material, the weight ratio between the 1,3,5-triazine derivative and the carbazole or carboline derivative is 1:5 to 5:1.

[0233] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one of the compounds shown in formulas BN-1R to BN-400R and BN-1S to BN-400S (content is 0.3wt-30.0wt%); the main material (content is 99.7wt-70.0wt%) is composed of any one of the 1,3,5-triazine derivatives shown in formulas TRZ-1 to TRZ-56 and any one of the carbazole or carboline derivatives shown in formulas H1-1 to H1-427. For example, in the main material, the weight ratio between the 1,3,5-triazine derivative and the carbazole or carboline derivative is 1:5 to 5:1.

[0234] In one embodiment of the present invention, the organic electroluminescent device further comprises a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer sequentially formed on the substrate; the organic light-emitting functional layer comprises a light-emitting layer containing the organic electroluminescent composition as described above, and may further comprise any one or a combination of multiple of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer.

[0235] In one embodiment of the present invention, in the organic electroluminescent device, the material of the hole injection layer is PEDOT:PSS, the material of the hole transport layer is Poly-HTL,

[0236] The material of the light-emitting layer is the boron nitrogen compound shown in Formula I and

[0237] The material of the electron transport layer is TmPyPB;

[0238] The material of the cathode layer is Al.

[0239] The present invention also provides an application of the organic electroluminescent device in an organic electroluminescent display or an organic electroluminescent lighting source.

[0240] Unless otherwise specified, all technical and scientific terms used herein have the common meaning in the field to which the claimed subject matter belongs. If there are multiple definitions for a term, the definition herein shall prevail.

[0241] Those skilled in the art will appreciate that the symbols used in the structural formulas of the groups described in this application are based on the conventions used in the art. or It means that a certain atom (such as a C atom or a N atom) on the corresponding group is connected to a certain fragment or group of a certain compound through a single bond.

[0242] Unless otherwise stated, when disclosing or claiming any type of range (such as wavelength, half-peak width and number of substituents), it is intended to disclose or claim separately each possible value that the range may reasonably cover, including any sub-ranges contained therein. For example, the numerical ranges defined in the substituents herein, such as 0 to 6, 1-4, 1 to 3, etc., indicate integers within the range, wherein 0-6 should be understood to include 0, 1, 2, 3, 4, 5, 6, and also include 1-4 and 1-3.

[0243] The words "include", "contain" or "comprises" and the like used in the present disclosure mean that the elements preceding the word include the elements listed after the word and their equivalents, without excluding unrecorded elements. The terms "contain" or "includes" used herein may be open, semi-closed and closed. In other words, the term also includes "consisting essentially of" or "consisting of".

[0244] As used herein, the terms "part", "moiety", "chemical moiety", "group", "chemical group" refer to a specific fragment or functional group in a molecule. A chemical moiety is generally considered to be a chemical entity embedded in or attached to a molecule.

[0245] It should be understood that singular forms (such as "a", "an" and "the") used in the present disclosure may include plural references unless otherwise specified.

[0246] Unless otherwise specified, the present disclosure adopts standard nomenclature and standard laboratory procedures and techniques for analytical chemistry, organic synthetic chemistry and optics. In some cases, standard techniques are used for chemical synthesis, chemical analysis, and light-emitting device performance testing. Unless otherwise specified, the present disclosure adopts traditional methods of mass spectrometry and elemental analysis, and each step and condition can refer to the conventional operating steps and conditions in the art.

[0247] The compounds of the present disclosure may contain non-natural ratios of atomic isotopes on one or more atoms constituting the compound. For example, radioactive isotope labeled compounds may be used, such as deuterium (2H). All isotopic changes of the compounds of the present disclosure, whether radioactive or not, are included within the scope of the present invention.

[0248] In the present disclosure, unless otherwise specified, the number of the substituents may be one or more; when there are multiple substituents, the number may be 2, 3 or 4. Furthermore, when there are multiple substituents, the substituents are independent of each other and may be the same or different.

[0249] In the present disclosure, the position of "substitution" can be any position unless otherwise specified.

[0250] In the present disclosure, unless otherwise specified, the hydrogen or H mentioned herein refers to the hydrogen element at natural abundance, i.e., a mixture of isotopes of protium, deuterium and tritium, wherein the abundance of protium is 99.98%.

[0251] In the present disclosure, deuterium is D or 2H, also known as heavy hydrogen.

[0252] In the present disclosure, the abundance of deuterium at the deuterium substitution site is greater than 95%.

[0253] Definitions of standard chemical terms may be found in reference literature including Carey and Sundberg "ADVANCED ORGANIC CHEMISTRY 4THED." Vols. A (2000) and B (2001), Plenum Press, New York.

[0254] In this specification, groups and substituents thereof may be selected by those skilled in the art to provide stable structural moieties and compounds. When substituents are described by conventional chemical formulas written from left to right, the substituents also include chemically equivalent substituents obtained when the structural formula is written from right to left. For example, -CH2O- is equivalent to -OCH2-.

[0255] As used herein, the term "halogen" or "halo" refers to fluorine, chlorine, bromine or iodine. In one embodiment, the halogen or halo is preferably fluorine or fluoro.

[0256] The term "alkyl" means a saturated aliphatic hydrocarbon group including both branched and straight chains having a specified number of carbon atoms. For example, C1-C20 alkyl includes straight or branched alkyl groups having 1-20 carbon atoms. As defined in "C1-C6 alkyl", groups having 1, 2, 3, 4, 5, or 6 carbon atoms in a straight or branched structure are included. For example, in the present disclosure, the C1-C6 alkyl groups are each independently methyl, ethyl, propyl, butyl, pentyl or hexyl; wherein the propyl group is a C3 alkyl group (including isomers, such as n-propyl or isopropyl); the butyl group is a C4 alkyl group (including isomers, such as n-butyl, sec-butyl, isobutyl or tert-butyl); the pentyl group is a C5 alkyl group (including isomers, such as n-pentyl, 1-methyl-butyl, 1-ethyl-propyl, 2-methyl-1-butyl, 3-methyl-1-butyl, isopentyl, tert-pentyl or neopentyl); and the hexyl group is a C6 alkyl group (including isomers, such as n-hexyl or isohexyl).

[0257] "Substituted alkyl" refers to an alkyl group substituted at any available point of attachment with one or more substituents, preferably 1 to 4 substituents. The term "haloalkyl" refers to an alkyl group having one or more halogen substituents, such as halomethyl, including but not limited to groups such as -CH2Br, -CH2I, -CH2Cl, -CH2F, -CHF2 and -CF3.

[0258] In the present disclosure, as a group or part of other groups, the term "Cn-m aryl" refers to a monocyclic or polycyclic aromatic group having n to m ring carbon atoms (ring atoms are only carbon atoms), which has at least one carbon ring with a conjugated π electron system. Examples of the above aryl units include phenyl, naphthyl, indenyl, azulenyl, fluorenyl, phenanthrenyl, or anthracenyl. In one embodiment, the aryl is preferably C 6-14 Aryl groups include, for example, phenyl and naphthyl, and more preferably phenyl.

[0259] In the present disclosure, as a group or part of other groups, the term "nm-membered heteroaryl" refers to an aromatic group whose ring atoms contain one or more (e.g., 1, 2, 3, and 4) heteroatoms selected from nitrogen, oxygen, and sulfur, and whose ring atoms are n to m, and the heteroaryl is a monocyclic, bicyclic, tricyclic, or tetracyclic ring system, wherein at least one ring is aromatic. Heteroaryl within the scope of this definition includes, but is not limited to, acridinyl, carbazolyl, cinnolinyl, quinoxalinyl, pyrazolyl, indolyl, benzotriazolyl, furanyl, thienyl, benzothienyl, benzofuranyl, quinolyl, isoquinolyl, oxazolyl, isoxazolyl, pyrazinyl, pyridazinyl, pyridinyl, pyrimidinyl, pyrrolyl, tetrahydroquinoline, imidazolyl, triazolyl, tetrazolyl, thiazolyl, isothiazolyl, furazanyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, purinyl, pteridinyl, naphthyridinyl, quinazolinyl, phthalazinyl, imidazopyridinyl, imidazothiazolyl, imidazooxazolyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, isoindolyl, indazolyl, pyrrolopyridinyl, thienopyridinyl, furopyridinyl, benzothiadiazolyl, benzoxadiazolyl, pyrrolopyrimidinyl, thienofuranyl. In one embodiment, preferred examples of the “5- to 18-membered heteroaryl” include furanyl, thienyl, pyrrolyl, imidazolyl, thiazolyl, pyrazolyl, oxazolyl, isoxazolyl, isothiazolyl, pyridinyl, pyrimidinyl and carbazolyl, and more preferably carbazolyl.

[0260] The term Cn-Cm cycloalkyl as used herein refers to a monocyclic or polycyclic alkyl group having n to m carbon atoms, for example C7-C 10 Bicyclic or tricyclic cycloalkyl and C3-C6 monocyclic cycloalkyl. Examples include adamantyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and bicycloheptyl. In one embodiment, C3-C6 10The cycloalkyl group is preferably adamantyl or cyclohexyl.

[0261] Without violating the common sense in the art, the above-mentioned preferred conditions can be arbitrarily combined to obtain the preferred embodiments of the present invention.

[0262] The reagents and raw materials used in the present invention are commercially available.

[0263] The positive and progressive effect of the present invention is that the applicant has combined the electron-withdrawing group with a chiral structure (binaphthalene derivative) with the resonant DA molecular skeleton through conjugated linkage through creative labor, and obtained the boron nitrogen compound described in Formula I of the present invention. The boron nitrogen compound of the present invention emits light in the green to red light region and has a narrow spectrum luminescence characteristic, and can also effectively adjust the emission wavelength to achieve fine regulation of the emission wavelength range of 493-613nm. Further provided are organic electroluminescent compositions and organic electroluminescent devices that emit light in the green to red light region and have narrow spectrum luminescence characteristics. The boron nitrogen compounds provided by the present disclosure and their compositions with some materials can be used as luminescent materials to prepare the luminescent layer of the organic electroluminescent device. The organic electroluminescent device prepared here has the advantages of narrow emission spectrum (relative to the electroluminescent spectrum of the separated DA structure luminescent material), high efficiency, circularly polarized luminescence, etc. The narrow emission spectrum can ensure the high color purity of the light-emitting device, and the circularly polarized luminescence eliminates or effectively reduces the light loss and device power consumption of the light-emitting device when the light passes through the anti-reflection polarization optical film. BRIEF DESCRIPTION OF THE DRAWINGS

[0264] Figure 1 Schematic diagram of the structure of the organic electroluminescent device in Example 3, wherein 1 is a substrate, 2 is an ITO anode, 3 is a hole transport layer, 4 is a light-emitting layer, 5 is an electron transport layer, 6 is an electron injection layer, and 7 is a metal cathode.

[0265] Figure 2 is the circular dichroism absorption spectrum of BN-7R / BN-7S dichloromethane solution, where the concentration of BN-107R / BN-107 is 2X10 -5 M.

[0266] Figure 3 is the circular dichroism absorption spectrum of BN-107R / BN-107 dichloromethane solution, where the concentration of BN-107R / BN-107 is 2X10 -5 M.

[0267] Figure 4 The photoluminescence spectra of BN-7R:(3wt%):H1-48 and BN-7S:(3wt%):H1-48 doped films, where the thickness of the film is 100 nm.

[0268] Figure 5The photoluminescence spectrum of BN-107R (3 wt%):H1-48 and BN-107S doped films, where the thickness of the film is 100 nm.

[0269] Figure 6 The electroluminescence spectra of BN-7R: (3 wt%): H1-48 and BN-7S: (3 wt%): H1-48 doped films, where the thickness of the film is 100 nm.

[0270] Figure 7 This is the electroluminescence spectrum of BN-107R (3wt%):H1-48 and BN-107S doped films, where the thickness of the film is 100nm. DETAILED DESCRIPTION

[0271] The present invention is further described below by way of examples, but the present invention is not limited to the scope of the examples. The experimental methods in the following examples without specifying specific conditions are carried out according to conventional methods and conditions, or selected according to the product specifications.

[0272] The mass spectra (MS) of molecules with a relative molecular weight below 1000 were measured by ITQ1100 ion trap gas chromatography-mass spectrometry from Thermo Fisher, and the mass spectra of molecules with a relative molecular weight above 1000 were measured by Autoflex Speed ​​matrix-assisted laser desorption / time-of-flight mass spectrometry from Bruker. The elemental analysis of the final product was performed by Flash EA1112 from Elemental Analysis.

[0273] The UV-visible absorption spectrum of the sample film was measured by a LAMBDA 35 UV-visible spectrophotometer from PerkinElmer. The fluorescence spectrum was measured by a RF-5301PC fluorescence photometer from Shimadzu Corporation of Japan. The excitation wavelength selected during the test was the maximum absorption wavelength.

[0274] According to conventional synthetic ideas, researchers in this field usually synthesize molecules containing a tri-coordinated B resonance skeleton and a cyano-substituted phenyl derivative group according to the following reaction route (3). In the following reaction test, Ar is a phenyl derivative with a strong electron-withdrawing group CN. Our experimental research results show that the tri-coordinated B structure cannot be formed according to the following reaction route, that is, the boron atom cannot coordinate with 1,3-dicarbazole (or its derivative) benzene under this condition, and the target product cannot be obtained according to this reaction mode. The main reason is that when the strong electron-withdrawing group cyano-substituted phenyl derivative exists, its para-position carbon atom is in an electron-deficient state, that is, the electron cloud density is low, resulting in the inability of the carbon atom to form a covalent bond with the boron atom. In addition, the cyano group will undergo chemical reactions and transform into other groups.

[0275]

[0276] The basic process route for synthesizing the compounds involved in the present invention is as follows, and the reaction is divided into four steps. The first two steps are synthesized as BNCz mother nucleus synthesis; the core of the final product synthesis is the successful preparation of the precursor BN-Bpin. The initially synthesized boron nitrogen mother nucleus containing a carbazole skeleton is used as a reactant, dissolved in tetrahydrofuran, and under the conditions of adding 1% equivalent of the main catalyst methoxy (cyclooctadiene) iridium dimer and 2% equivalent of the co-catalyst 4,4'-di-tert-butyl-2,2'-bipyridine, the reaction system is heated to reflux, and the boron atom replaces the para-position hydrogen atom of the benzene ring to activate and be replaced by a boron ester.

[0277] Then, a variety of electron-withdrawing compounds can be flexibly obtained through a simple Suzuki reaction.

[0278]

[0279] in

[0280] R n -Br is the following four chiral compounds:

[0281]

[0282] Chirality R n -Br is prepared by the following steps

[0283]

[0284] The specific raw materials-1 used include the following molecules:

[0285] The specific raw materials-2 used include the following molecules:

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292] The specific raw materials-3 used include the following molecules:

[0293]

[0294] The specific raw materials-4 used include the following molecules

[0295]

[0296] Synthesis Example

[0297] The general reaction steps are as follows:

[0298] In the first step, 60 ml of anhydrous DMF (N, N-dimethylformamide) solution containing 35.2 mmol of raw material-2 is slowly added dropwise to 50 ml of anhydrous DMF solution containing 5.4 g of potassium tert-butoxide (48.0 mmol), and after stirring at room temperature for 2 hours, 20 ml of anhydrous DMF solution containing 3.1 g of 2-bromo-1,3-difluorobenzene (16.0 mmol) is added dropwise thereto. The reaction system is stirred at 140 ° C for 24 hours, then cooled to room temperature and poured into ice water. The white solid is filtered out, dried in a vacuum, and then further purified by column chromatography using a mixed eluent of dichloromethane / petroleum ether to obtain the intermediate BrNCz as a white solid.

[0299] In the second step, under the protection of nitrogen atmosphere, 19.4mL of n-hexane solution of tert-butyl lithium (25.2mmol) was slowly added to 100mL of tert-butylbenzene solution (-30℃) containing 12.6mmol of intermediate BrNCz. After slowly heating to 60℃ and stirring for 2 hours, n-hexane was removed in vacuo, then cooled to -30℃, 2.4mL of boron tribromide (6.3mmol) was added, and the reaction mixture was stirred at room temperature for 1 hour. Then 15.6mL of N, N-diisopropylethylamine (91.1mmol) was added at 0℃, and then the reaction mixture was heated to 130℃ and continued to stir for 5 hours, and then cooled to room temperature. 5ml of methanol was added to the reaction mixture to quench the residual BBr3. The reaction system was concentrated in vacuo and purified by column chromatography with a mixture of dichloromethane / petroleum ether to obtain the BNCz mother core.

[0300] In the third step, at room temperature, a boron-nitrogen raw material containing a carbazole skeleton (6.5 mmol) and 1.7 g of biboric acid pinacol ester (6.5 mmol) were added to tetrahydrofuran (60 mL), the mixture was bubbled with nitrogen for 10 minutes, and 34.9 mg of 4,4'-di-tert-butyl-2,2'-bipyridine (0.13 mmol) and 43.1 mg of methoxy (cyclooctadiene) iridium dimer (0.065 mmol) were added under high flow nitrogen. After stirring for 10 minutes, the mixture was heated to reflux and stirred for 24 hours. After the reaction system was cooled to room temperature, it was directly concentrated under reduced pressure and purified by column chromatography to obtain the precursor BN-Bpin.

[0301] In the fourth step, (octahydro)bi-2-naphthol (1.5 mmol), potassium carbonate (4.5 mmol) and bromodifluorobenzonitrile (1.5 mmol) were added to 20 ml of anhydrous DMF, and the reaction system was stirred at 120° C. for 16 hours, then cooled to room temperature and poured into ice water. The white solid was filtered out, dried in vacuo, and then further purified by column chromatography using a mixed eluent of dichloromethane / petroleum ether to obtain chiral intermediate R n -Br, as a white solid.

[0302] Step 5: R n -Br (0.6mmol), BN-Bpin (0.5mmol), 0.14g potassium carbonate (1mmol) and water (2mL) were added to tetrahydrofuran (16mL), the mixture was bubbled with nitrogen for 10 minutes, and 28.9mg tetrakis (triphenylphosphine) palladium (0.025mmol) was added under high flow nitrogen. The mixture was heated to reflux and stirred for 12 hours. After the reaction system was cooled to room temperature, the reaction mixture was extracted with dichloromethane and water, the organic phase was heated and dried under vacuum, and then purified by column chromatography to obtain the target product BN-n (n = 1-400).

[0303] Taking compound BN-7 as an example, the specific details of the synthetic example experiment are as follows: the first step is to slowly drop 60 ml of anhydrous DMF (N, N-dimethylformamide) solution containing 9.8 g of 3,6-di-tert-butylcarbazole (35.2 mmol) into 50 ml of anhydrous DMF solution containing 5.4 g of potassium tert-butoxide (48.0 mmol), and after stirring at room temperature for 2 hours, 20 ml of anhydrous DMF solution containing 3.1 g of 2-bromo-1,3-difluorobenzene (16.0 mmol) is added dropwise. The reaction system is stirred at 140 ° C for 24 hours, then cooled to room temperature and poured into ice water. The white solid is filtered out, dried in a vacuum, and then further purified by column chromatography using a mixed eluent of dichloromethane / petroleum ether to obtain 10.5 g of the intermediate BrNCz as a white solid (yield 92%).

[0304] In the second step, under the protection of nitrogen atmosphere, 19.4mL of n-hexane solution of tert-butyl lithium (25.2mmol) was slowly added to 100mL of tert-butylbenzene solution (-30°C) containing 9.0g (12.6mmol) of intermediate BrNCz-7. After slowly heating to 60°C and stirring for 2 hours, n-hexane was removed in vacuo, then cooled to -30°C, 2.4mL of boron tribromide (6.3mmol) was added, and the reaction mixture was stirred at room temperature for 1 hour. Then 15.6mL of N, N-diisopropylethylamine (91.1mmol) was added at 0°C, and then the reaction mixture was heated to 130°C and continued to stir for 5 hours, and then cooled to room temperature. 5ml of methanol was added to the reaction mixture to quench the residual BBr3. The reaction system was concentrated in vacuo and purified by column chromatography with a mixture of dichloromethane / petroleum ether to obtain 2.9g of BNCz-7 mother core as a yellow solid (yield 35%) (the experiment can be repeated many times to enrich the raw material).

[0305] In the third step, 4.2 g BNCz-7 (6.5 mmol) and 1.7 g pinacol diboronate (6.5 mmol) were added to tetrahydrofuran (60 mL) at room temperature, the mixture was bubbled with nitrogen for 10 minutes, and 34.9 mg 4,4'-di-tert-butyl-2,2'-bipyridine (0.13 mmol) and 43.1 mg methoxy(cyclooctadiene)iridium dimer (0.065 mmol) were added under high flow nitrogen. After stirring for 10 minutes, the mixture was heated to reflux and stirred for 24 hours. After the reaction system was cooled to room temperature, it was directly concentrated under reduced pressure and purified by column chromatography to obtain the precursor 4.5 g BN-7-Bpin ([m / z] + :767.48) (yield 90%).

[0306] In the fourth step, 441.6 mg of octahydro-bi-2-naphthol (R configuration) (1.5 mmol), 621.9 mg of potassium carbonate (4.5 mmol) and 327.0 mg of 4,5-difluoro-2-bromobenzonitrile (1.5 mmol) were added to 20 ml of anhydrous DMF, and the reaction system was stirred at 120° C. for 16 hours, then cooled to room temperature and poured into ice water. The white solid was filtered out, dried in vacuo, and then further purified by column chromatography using a mixed eluent of dichloromethane / petroleum ether to obtain 637.7 mg of chiral intermediate R n -Br(R configuration) ([m / z] + : 473.38), as a white solid (yield 90%).

[0307] Step 5: 283.2 mg R n-Br (R configuration) (0.6mmol), 383mg BN-7-Bpin (0.5mmol), 0.14g potassium carbonate (1mmol) and water (2mL) were added to tetrahydrofuran (16mL), the mixture was bubbled with nitrogen for 10 minutes, and 28.9mg tetrakis (triphenylphosphine) palladium (0.025mmol) was added under high flow nitrogen. The mixture was heated to reflux and stirred for 12 hours. After the reaction system was cooled to room temperature, the reaction mixture was extracted with dichloromethane and water, the organic phase was heated and dried under vacuum, and then purified by column chromatography to obtain 252mg of the target product BN-7 (R configuration) as a yellow solid (yield 58%).

[0308] The compounds were synthesized according to the above steps. The elemental analysis (percentage of C, H and N in the compounds), mass spectrometry molecular weight and synthesis reaction yield data (total yield of the five-step reaction) of the compounds BN-1R to BN-400R and BN-1S to BN-400S of the present invention are shown in Table 1.

[0309] Table 1

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335] Effect Example 1

[0336] BN-7R / BN-7S was prepared into a dichloromethane solution (concentration: 2X10 -5 M), and then test its circular dichroism (CD) absorption spectrum ( Figure 2 ), the test results show that the circular dichroism absorption spectra of BN-7R and BN-7S show positive-negative symmetrical distribution, indicating that BN-7R and BN-7S are enantiochiral isomers.

[0337] Prepare BN-107R / BN-107S into dichloromethane solution (concentration: 2X10 -5 M), and then test its circular dichroism (CD) absorption spectrum ( Figure 3 ), the test results show that the circular dichroic dispersion absorption spectra of BN-107R and BN-107S show positive-negative symmetrical distribution, indicating that BN-107R and BN-107S are enantiomeric chiral isomers. Organic luminescent molecules with a single chiral structure have circularly polarized luminescence properties.

[0338] Effect Example 2

[0339] The luminescent molecular structures used in the comparative effect examples are as follows:

[0340]

[0341]

[0342] The compounds shown in formula BN-1 / R to BN-400 / R and BN-1 / S to BN-400 / S are the molecular structures of the materials provided by the present disclosure (the specific molecular structures are shown above), and the compounds shown in BN-T-1 to BN-T-8 are the molecular structures of comparative materials. Any compound shown in formula BN-1 / R to BN-400 / R and BN-1 / S to BN-400 / S is used as a doped luminescent material and H1-1 is used as a main material to prepare a doped film (thickness of 150±15nm), the doping concentration of the doped luminescent material is 3wt% (weight percentage concentration), and then the emission spectrum of the doped film is tested respectively, and the test results are listed in Table 2.

[0343] The comparison of the luminescent peak positions of the luminescent compounds provided by the present disclosure and the corresponding luminescent peak positions of the comparative compounds listed in Table 2 shows that the luminescent peak of the luminescent compounds provided by the present disclosure is red-shifted by 6-37nm compared with the luminescent peak position of the corresponding comparative compound, that is, it is shifted by 6-37nm to a long wavelength. The above-mentioned effect examples prove that the luminescent peak of the boron nitrogen compound disclosed in the present disclosure is red-shifted relative to the comparative compound, while the half-peak width of the luminescent spectrum is not significantly deteriorated (still narrow), so the luminescent molecule design principle and method provided by the present disclosure are effective in providing a luminescent material with a narrow emission peak in the green light region to the red light region.

[0344] Table 2

[0345]

[0346]

[0347]

[0348] The molecular structures of some materials involved in the device effect embodiments are as follows:

[0349]

[0350] The following is an example of an electroluminescent device prepared using the materials disclosed in the present invention, and the specific device preparation process is as follows:

[0351] (1) Substrate treatment: Transparent ITO glass is used as the substrate material for the preparation of the device. It is first ultrasonically treated with 5% ITO washing solution for 30 minutes, then ultrasonically washed with distilled water (2 times), acetone (2 times), and isopropanol (2 times) in sequence, and finally the ITO glass is stored in isopropanol. Before each use, carefully wipe the surface of the ITO glass with acetone cotton balls and isopropanol cotton balls, rinse with isopropanol and dry, and then treat with plasma for 5 minutes for use. The preparation of the device is completed by combining spin coating and vacuum evaporation process.

[0352] (2) Preparation of hole injection layer and hole transport layer: First, a 20 nm thick layer of PEDOT:PSS (poly (3,4-ethylenedioxythiophene):polystyrene sulfonate) was spin-coated on the surface of ITO as a hole injection layer, and then a 50 nm thick Poly-HTL was spin-coated on the hole injection layer as a hole transport layer. The ITO glass with the hole injection layer and the hole transport layer was then placed in a nitrogen-protected glove box and annealed at 200°C for 30 min (to allow the Poly-HTL to cross-link).

[0353] (3) Preparation of light-emitting layer: The main material and the light-emitting material are dissolved in xylene in a ratio of 97wt%:3wt% (wt% is the weight percentage concentration) to prepare a solution with a concentration of 2wt%. The light-emitting layer is prepared by spin coating using the prepared solution. The thickness of the light-emitting layer is 50nm.

[0354] (4) Preparation of electron transport layer, electron injection layer and metal electrode: The electron transport layer, electron injection layer and metal electrode are prepared by evaporation process. When the vacuum degree of vacuum evaporation system reaches 5×10 -4 When the thickness is below 100 Pa, the deposition rate is measured by a film thickness meter. The organic electron transport layer, the LiF electron injection layer and the metal Al electrode are sequentially deposited on the light-emitting layer using a vacuum deposition process (see the following effect example for the specific device structure). The deposition rate of the organic material is The deposition rate of LiF is The deposition rate of Al is

[0355] The device's current, voltage, brightness, luminescence spectrum and other characteristics were tested synchronously using a Photo Research PR 655 spectral scanning luminance meter and a Keithley K 2400 digital source meter system. The device's performance test was carried out at room temperature and in an ambient atmosphere. The device's external quantum efficiency (EQE) was calculated from the current density, brightness and electroluminescence spectrum combined with the visibility function under the condition of a Lambertian distribution of luminescence.

[0356] Effect Example 3

[0357] In the effect example 3, the organic electroluminescent device (structured as Figure 1As shown in the figure, PEDOT:PSS is used as a hole injection layer, Poly-HTL is used as a hole transport layer, H1-48 is used as a main material in the light-emitting layer, some chiral BN compounds (see Table 1) are used as doped light-emitting materials (doping concentration is 3wt%), TRZ-1 is used as an electron transport material, LiF is used as an electron injection layer, and Al is used as a metal cathode. The structure of the organic electroluminescent device of the effect embodiment is [ITO / PEDOT:PSS (20nm) / Poly-HTL (50nm) / H1-48+3wt%BN-n / TRZ-1 (50nm) / LiF (1nm) / Al (100nm)]. Wherein n=1-618. The results of the effect embodiment are shown in Table 3.

[0358] The electroluminescent device effect implementation data listed in Table 3 proves that the luminescent material provided by the present disclosure can be used to prepare high-efficiency organic electroluminescent devices, and the electroluminescent spectrum has a narrow band characteristic, and the half-peak width of the electroluminescent spectrum is less than 60nm.

[0359] Table 3. Main parameters of electroluminescent performance

[0360]

[0361]

[0362]

[0363] Effect Example 4

[0364] In the effect example 4, the organic electroluminescent device (structured as Figure 1 As shown in the figure, PEDOT:PSS (used as a hole injection layer, Poly-HTL used as a hole transport layer, H1-48 and TRZ-1 (the weight ratio of H1-48 and TRZ-1 is 1:2) are used as the main material in the light-emitting layer, some chiral BN compounds (see Table 1) are used as doped light-emitting materials (doping concentration is 3wt%), TRZ-1 is used as an electron transport material, LiF is used as an electron injection layer, and Al is used as a metal cathode. The structure of the organic electroluminescent device of the effect embodiment is [ITO / PEDOT:PSS (20nm) / Poly-HTL (50nm) / H1-48:TRZ-1+3wt%BN-n / TRZ-1 (50nm) / LiF (1nm) / Al (100nm)]. Wherein n=1-618. The results of the effect embodiment are shown in Table 4.

[0365] The electroluminescent device effect implementation data listed in Table 4 proves that the luminescent material provided by the present disclosure can be used to prepare high-efficiency organic electroluminescent devices, and the electroluminescent spectrum has a narrow band characteristic, and the half-peak width of the electroluminescent spectrum is less than 60nm.

[0366] Table 4. Main parameters of electroluminescent performance

[0367]

[0368]

[0369] The above description is merely an exemplary embodiment of the present invention and is not intended to limit the protection scope of the present invention. The protection scope of the present invention is determined by the appended claims.

Claims

1. A boron nitrogen compound as shown in formula I: in, R 1 and R 2 are independently H, halogen, C1-C 20 Alkyl, with one or more R a Substituted C1-C 20 Alkyl, -O-C1-C 20 Alkyl, with one or more R b Substituted-O-C1-C 20 Alkyl, C3-C 10 Cycloalkyl, with one or more R c Substituted C3-C 10 Cycloalkyl, C6-C 14 Aryl, one or more R d Substituted C6-C 14 Aryl, 5-18 membered heteroaryl, substituted by one or more R e Substituted 5-18 membered heteroaryl or -NR 3 R 4 , the 5-18 membered heteroaryl and one or more R e The heteroatoms in the substituted 5-18 membered heteroaryl group are independently one or more of N, S and O, and the number of the heteroatoms is 1, 2 or 3; R a is halogen, CN or -O-C1-C 12 alkyl; R b , R c , R d and R e are independently halogen, CN, C1-C 12 Alkyl or -O-C1-C 12 alkyl; R 3 and R 4 Independently C6-C 14 Aryl or one or more R f Substituted C6-C 14 Aryl, Or, R 3 and R 4 The nitrogen atom to which it is attached independently forms a 5-18 membered heteroaryl group or is replaced by one or more R g substituted 5-18 membered heteroaryl, The 5-18 membered heteroaryl group and one or more R g The heteroatoms in the substituted 5-18 membered heteroaryl group are independently one or more of N, S and O, and the number of the heteroatoms is 1, 2 or 3; R f and R g are independently halogen, CN, C1-C 12 Alkyl or -O-C1-C 12 alkyl; R n for is the chiral axis, indicating S or R configuration; R n1 , R n2 , R n3 and R n4 are independently H or cyano, and "R n1 , R n2 and R n3 ” or "R n1 , R n2 and R n4 " at least one of which is a cyano group; R n5 and R n6 , or, R n7 and R n8 The carbon atoms to which it is attached independently form a 5-6 membered cycloalkyl group, which is supported by one or more R n5 -1 Substituted 5-6 membered cycloalkyl, C6-C 14 Aryl or 1 or more R n5-2 Substituted C6-C 14 Aryl; R n5-1 and R n5-2 are independently H, halogen, C1-C 20 Alkyl or -O-C1-C 20 alkyl.

2. The boron-nitrogen compound of formula (I) according to claim 1, characterized in that: The boron nitrogen compound as shown in formula I is any of the following schemes: Option A: R 1 are independently H, C1-C 20 Alkyl, -O-C1-C 20 Alkyl, C3-C 10 Cycloalkyl, C6-C 14 Aryl, one or more R d Substituted C6-C 14 Aryl or -NR 3 R 4 ; R d C1-C 12 Alkyl or -O-C1-C 12 alkyl; R 3 and R 4 Independently C6-C 14 Aryl or one or more R f Substituted C6-C 14 Aryl; Or, R 3 and R 4 Together with the nitrogen atom to which it is attached, it forms a 5-18 membered heteroaryl group or is replaced by one or more R g substituted 5-18 membered heteroaryl; R f Independently C1-C 12 Alkyl or -O-C1-C 12 alkyl; R g Independently C1-C 12 alkyl; R n for "R n1 , R n2 and R n3 ” or "R n1 , R n2 and R n4 "One of them is cyano and the other two are hydrogen; R n5 and R n6 , or, R n7 and R n8 The carbon atoms to which it is attached independently form a 5-6 membered cycloalkyl or a C6-C 14 Aryl; Option B: R 1 are independently H, C1-C 20 Alkyl, C6-C 14 Aryl, one or more R d Substituted C6-C 14 Aryl or -NR 3 R 4 ; R d Independently C1-C 12 alkyl; R 3 and R 4 Independently C6-C 14 Aryl or one or more R f Substituted C6-C 14 Aryl; Or, R 3 and R 4 Together with the nitrogen atom to which it is attached, it forms a 5-18 membered heteroaryl group or is replaced by one or more R g substituted 5-18 membered heteroaryl; R f and R g Independently C1-C 12 alkyl; R n for "R n1 , R n2 and R n3 ” or "R n1 , R n2 and R n4 "One of them is cyano and the other two are hydrogen; R n5 and R n6 , or, R n7 and R n8 The carbon atoms to which it is attached independently form a 5-6 membered cycloalkyl or a C6-C 14 Aryl; Option C: R 1 are independently H, C1-C 20 Alkyl, C6-C 14 Aryl or one or more R d Substituted C6-C 14 Aryl; R d Independently C1-C 12 alkyl; R 3 and R 4 Independently C6-C 14 Aryl or one or more R f Substituted C6-C 14 Aryl; Or, R 3 and R 4 Together with the nitrogen atom to which it is attached, it forms a 5-18 membered heteroaryl group or is replaced by one or more R g substituted 5-18 membered heteroaryl; R f and R g Independently C1-C 12 alkyl; R n for "R n1 , R n2 and R n3 ” or "R n1 , R n2 and R n4 "One of them is cyano and the other two are hydrogen; R n5 and R n6 , or, R n7 and R n8 The carbon atoms to which it is attached independently form a 5-6 membered cycloalkyl or a C6-C 14 Aryl.

3. The boron nitrogen compound as shown in formula I according to claim 1, characterized in that R 1 are independently H, C1-C 20 Alkyl, -O-C1-C 20 Alkyl, C3-C 10 Cycloalkyl, C6-C 14 Aryl, one or more R d Substituted C6-C 14 Aryl or -NR 3 R 4 ; and / or, R 2 Independently C1-C 20 Alkyl, -O-C1-C 20 Alkyl, C3-C 10 Cycloalkyl, C6-C 14 Aryl, one or more R d Substituted C6-C 14 Aryl or -NR 3 R 4 ; and / or, R d Independently C1-C 12 alkyl; and / or, R 3 and R 4 Together with the nitrogen atom to which it is attached, it forms a 5-18 membered heteroaryl group or is replaced by one or more R g substituted 5-18 membered heteroaryl; and / or, R n for R n1 , R n2 , R n3 and R n4 are independently H or cyano, and "R n1 , R n2 and R n3 ” or "R n1 , R n2 and R n4 " at least one of which is a cyano group; and / or, R n5 and R n6 , or, R n7 and R n8 The carbon atoms to which it is attached independently form a 5-6 membered cycloalkyl or a C6-C 14 Aryl.

4. The boron-nitrogen compound of formula (I) as claimed in claim 3, characterized in that: R 1 are independently H, C1-C 20 Alkyl, C6-C 14 Aryl, one or more R d Substituted C6-C 14 Aryl or -NR 3 R 4 ; and / or, R 2 Independently C1-C 20 Alkyl, C6-C 14 Aryl, one or more R d Substituted C6-C 14 Aryl or -NR 3 R 4 ; and / or, R 3 and R 4 Together with the nitrogen atom to which it is attached, it forms a g substituted 5-18 membered heteroaryl; and / or, R n for R n1 and R n2 For H, R n3 is cyano; and / or, R n5 and R n6 , or, R n7 and R n8 The carbon atoms to which they are attached independently form a 5-6 membered cycloalkyl group.

5. The boron-nitrogen compound of formula (I) as claimed in claim 4, characterized in that: R 1 Independently C1-C 20 Alkyl, C6-C 14 Aryl or one or more R d Substituted C6-C 14 Aryl; and / or, R 2 Independently C1-C 20 Alkyl, C6-C 14 Aryl, one or more R d Substituted C6-C 14 Aryl.

6. The boron nitrogen compound as shown in formula I according to claim 1, characterized in that When R 1 , R 2 , R a , R b , R c , R d and R e When independently halogen, the halogen is F, Cl, Br or I; and / or, when R 1 and R 2 Independently C1-C 20 Alkyl, with one or more R a Substituted C1-C 20 Alkyl, -O-C1-C 20 Alkyl, with one or more R b Substituted-O-C1-C 20 When the C1-C 20 Alkyl, said one or more R a Substituted C1-C 20 Alkyl, the -O-C1-C 20 The alkyl group and the b Substituted-O-C1-C 20 C1-C 20 The alkyl groups are independently C1-C 10 alkyl; and / or, when R 1 and R 2 Independently for C3-C 10 Cycloalkyl or one or more R c Substituted C3-C 10 When the cycloalkyl group is 10 The cycloalkyl group and the c Substituted C3-C 10 C3-C in cycloalkyl 10 The cycloalkyl groups are independently cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl or C7-C 10 tricyclic cycloalkyl; and / or, when R 1 and R 2 Independently C6-C 14 Aryl or one or more R d Substituted C6-C 14 In the case of an aryl group, the C6-C 14 Aryl or said one or more R d Substituted C6-C 14 C6-C in aromatic groups 14 Aryl is independently phenyl, naphthyl, anthracenyl or phenanthrenyl; and / or, when R 1 and R 2 Independently for one or more R d Substituted C6-C 14 When the group is aryl, the R d The number of is 1, 2 or 3; and / or, when R 1 and R 2 is independently a 5-18 membered heteroaryl or is replaced by one or more R e When the 5-18 membered heteroaryl is substituted, the 5-18 membered heteroaryl and the substituted by one or more R e The 5-18-membered heteroaryl in the substituted 5-18-membered heteroaryl is independently a 5-6-membered heteroaryl; and / or, when R a O-C1-C 12 When the -O-C1-C 12 Alkyl is -O-C1-C6 alkyl; and / or, when R b , R c , R d and R e Independently C1-C 12 Alkyl or -O-C1-C 12 When the C1-C 12 The alkyl group and the -O-C1-C 12 C1-C 12 Alkyl is independently C1-C6 alkyl; and / or, when R 3 and R 4 Independently C6-C 14 Aryl or one or more R f Substituted C6-C 14 In the case of an aryl group, the C6-C 14 Aryl is independently phenyl, naphthyl, anthracenyl or phenanthrenyl; and / or, when R 3 and R 4 The nitrogen atom to which it is attached independently forms a 5-18 membered heteroaryl group or is replaced by one or more R g When the 5-18 membered heteroaryl is substituted, the 5-18 membered heteroaryl and the substituted by one or more R g The 5-18-membered heteroaryl in the substituted 5-18-membered heteroaryl is independently a 5-13-membered heteroaryl, the heteroatom is N, and the number of the heteroaryl is 1; and / or, when R f and R g Independently C1-C 12 Alkyl or -O-C1-C 12 When the C1-C 12 The alkyl group and the -O-C1-C 12 C1-C 12 Alkyl is independently C1-C8 alkyl; and / or, when R n5 and R n6 , or, R n7 and R n8 Together with the carbon atom it is connected to, it independently forms a C6-C 14 Aryl or 1 or more R n5-2 Substituted C6-C 14 In the case of an aryl group, the C6-C 14 The aryl group and the n5-2 Substituted C6-C 14 C6-C in aromatic groups 14 Aryl is independently phenyl, naphthyl, anthracenyl or phenanthrenyl.

7. The boron nitrogen compound as shown in formula I according to claim 6, characterized in that When R 1 and R 2 Independently C1-C 20 Alkyl, with one or more R a Substituted C1-C 20 Alkyl, -O-C1-C 20 Alkyl, with one or more R b Substituted-O-C1-C 20 When the C1-C 20 Alkyl, said one or more R a Substituted C1-C 20 Alkyl, the -O-C1-C 20 The alkyl group and the b Substituted-O-C1-C 20 C1-C 20 The alkyl radicals are independently methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-hexyl, n-octyl, n-decyl or and / or, when R 1 and R 2 Independently for C3-C 10 Cycloalkyl or one or more R c Substituted C3-C 10 When the cycloalkyl group is C7-C 10 The tricyclic cycloalkyl group is adamantyl group; and / or, when R b , R c , R d and R e Independently C1-C 12 Alkyl or -O-C1-C 12 When the C1-C 12 The alkyl group and the -O-C1-C 12 C1-C 12 Alkyl is independently methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl or n-hexyl; and / or, when R 3 and R 4 Independently C6-C 14 Aryl or one or more R f Substituted C6-C 14 In the case of an aryl group, the C6-C 14 Aryl is independently phenyl; and / or, when R 3 and R 4 The nitrogen atom to which it is attached independently forms a 5-18 membered heteroaryl group or is replaced by one or more R g When the 5-18 membered heteroaryl is substituted, the 5-18 membered heteroaryl and the substituted by one or more R g The 5- to 18-membered heteroaryl groups in the substituted 5- to 18-membered heteroaryl groups are independently and / or, when R f and R g Independently C1-C 12 Alkyl or -O-C1-C 12 When the C1-C 12 The alkyl group and the -O-C1-C 12 C1-C 12 The alkyl radicals are independently methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-hexyl or and / or, when R n5 and R n6 , or, R n7 and R n8 Together with the carbon atom it is connected to, it independently forms a C6-C 14 Aryl or 1 or more R n5-2 Substituted C6-C 14 In the case of an aryl group, the C6-C 14 The aryl group and the n5-2 Substituted C6-C 14 C6-C in aromatic groups 14 Aryl is independently phenyl.

8. The boron nitrogen compound as shown in formula I according to claim 7, characterized in that When R 1 and R 2 Independently C1-C 20 Alkyl, with one or more R a Substituted C1-C 20 Alkyl, -O-C1-C 20 Alkyl, with one or more R b Substituted-O-C1-C 20 When the C1-C 20 Alkyl, said one or more R a Substituted C1-C 20 Alkyl, the -O-C1-C 20 The alkyl group and the b Substituted-O-C1-C 20 C1-C 20 Alkyl is independently methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl; and / or, when R f and R g Independently C1-C 12 Alkyl or -O-C1-C 12 When the C1-C 12 The alkyl group and the -O-C1-C 12 C1-C 12 The alkyl group is independently methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl.

9. The boron nitrogen compound as shown in formula I according to claim 6, characterized in that When R 1 and R 2 Independently for one or more R d Substituted C6-C 14 When the aryl group is d Substituted C6-C 14 The aryl groups are independently Or, when R 3 and R 4 Independently for one or more R f Substituted C6-C 14 When the aryl group is f Substituted C6-C 14 The aryl groups are independently Or, when R 3 and R 4 Together with the nitrogen atom to which it is attached, it forms a g When the 5-18 membered heteroaryl is substituted, the g The substituted 5-18 membered heteroaryl is or, Any of the following groups: In the above structure, -C4H9 is n-butyl, -C6H 13 is n-hexyl, -C8H 17 is n-octyl, -C 10 H 21 is n-decyl, -C 12 H 25 is n-dodecyl; or, R n for 10. The boron nitrogen compound as shown in formula I according to claim 1, characterized in that: The boron nitrogen compound as shown in formula I is any of the following compounds: Among them, -C4H9 in the structural formula is n-butyl, -C6H 13 is n-hexyl, -C8H 17 is n-octyl, -C 10 H 21 is n-decyl, -C 12 H 25 It is n-dodecyl.

11. The method for preparing the boron nitrogen compound as shown in formula I according to any one of claims 1 to 10, characterized in that: It includes the following steps: Under the action of an alkaline reagent and a catalyst, the compound represented by formula II and the compound represented by formula III are subjected to a Suzuki reaction in a solvent to obtain the boron nitrogen compound represented by formula I; Where X is a halogen, R 1 , R 2 and R n The definitions are as described in any one of claims 1 to 10.

12. A compound II or III: in, X is halogen, R 1 , R 2 , R n1 , R n2 , R n3 , R n4 , R n5 , R n6 , R n7 , R n8 and The definition as described in any one of claims 1 to 10; The compound II is not any of the following compounds: The * in the above structure connects this Group.

13. Compound III according to claim 12, characterized in that The compound III is the following compound:

14. An organic electroluminescent composition, characterized in that: It comprises a boron nitrogen compound as shown in formula I as described in any one of claims 1 to 10 and a host material.

15. The organic electroluminescent composition according to claim 14, characterized in that: In the organic electroluminescent composition, the boron nitrogen compound represented by formula I is 0.3-30.0 parts by weight; the host material is 99.7-70.0 parts by weight; And / or, the main material is a carbazole derivative main material and / or a carbazole derivative main material; The molecular structure of the main material of the carbazole derivative or the main material of the carbazole derivative is as shown in the following general formula H-1, H-2, H-3, H-4, H-5, H-6 or H-7: wherein X1, Y1 and Z1 are independently CH or N, and at most one of X1, Y1 and Z1 is N; R 1H and R 2H Independently any of the following groups: wherein X2, Y2 and Z2 are independently CH or N, and at most one of X2, Y2 and Z2 is N; R aH and R bH are independently H, C1-C 20 Alkyl, -O-C1-C 20 Alkyl, C6-C 20 Aryl, C1-C 20 Alkyl-substituted C6-C 20 Aryl or -O-C1-C 20 Alkyl-substituted C6-C 20 Aryl.

16. The organic electroluminescent composition according to claim 15, characterized in that: In the organic electroluminescent composition, the boron nitrogen compound as shown in formula I accounts for 0.3 parts by weight; and the main material accounts for 99.7 parts by weight.

17. The organic electroluminescent composition according to claim 15, characterized in that: The molecular structure of the carbazole derivative main material or the carbazole derivative main material is shown in the general formula H-1 or H-5.

18. The organic electroluminescent composition according to claim 15, characterized in that: When R aH and R bH Independently C1-C 20 Alkyl, -O-C1-C 20 Alkyl, C1-C 20 Alkyl-substituted C6-C 20 Aryl or -O-C1-C 20 Alkyl-substituted C6-C 20 In the case of an aryl group, the C1-C 20 Alkyl, the -O-C1-C 20 Alkyl, the C1-C 20 Alkyl-substituted C6-C 20 Aryl and the -O-C1-C 20 Alkyl-substituted C6-C 20 C1-C in aromatic groups 20 The alkyl groups are independently C1-C 12 alkyl; and / or, when R aH and R bH Independently C6-C 20 Aryl, C1-C 20 Alkyl-substituted C6-C 20 Aryl or -O-C1-C 20 Alkyl-substituted C6-C 20 In the case of an aryl group, the C6-C 20 Aryl, the C1-C 20 Alkyl-substituted C6-C 20 Aryl and the -O-C1-C 20 Alkyl-substituted C6-C 20 C6-C in aromatic groups 20 Arylalkyl is independently phenyl, naphthyl, phenanthryl or anthracenyl; and / or, when R aH and R bH Independently C1-C 20 Alkyl-substituted C6-C 20 When aryl or -, the C1-C 20 Alkyl-substituted C6-C 20 The aryl groups are independently 19. The organic electroluminescent composition according to claim 18, characterized in that: When R aH and R bH Independently C1-C 20 Alkyl, -O-C1-C 20 Alkyl, C1-C 20 Alkyl-substituted C6-C 20 Aryl or -O-C1-C 20 Alkyl-substituted C6-C 20 In the case of an aryl group, the C1-C 20 Alkyl, the -O-C1-C 20 Alkyl, the C1-C 20 Alkyl-substituted C6-C 20 Aryl and the -O-C1-C 20 Alkyl-substituted C6-C 20 C1-C in aromatic groups 20 The alkyl groups are independently Methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-hexyl or n-dodecyl.

20. The organic electroluminescent composition according to claim 15, characterized in that: The main carbazole derivative material or the main carbazole derivative material as shown in formula H-1, H-2, H-3, H-4, H-5, H-6 or H-7 is any of the following structures: Among them, -C4H9 in the structural formula is n-butyl, -C6H 13 is n-hexyl, -C 12 H 25 It is n-dodecyl.

21. The organic electroluminescent composition according to claim 15, characterized in that: The main material also includes 1,3,5-triazine derivatives; the molecular structure of the 1,3,5-triazine derivative main material is as shown in the following general formula Trz1-A, Trz2-A, Trz3-A or Trz4-A: R 1a , R 1b , R 2a , R 2b , R 3a and R 3b One or two of them are R Tz ; R 1a , R 1b , R 2a , R 2b , R 3a and R 3b wherein the rest are independently hydrogen, deuterium, C1-C8 alkyl, -O-C1-C8 alkyl, C6-C 18 Aryl, C1-C8 alkyl substituted C6-C 18 Aryl, -O-C1-C8 alkyl substituted C6-C 18 C6-C 18 The aromatic group; R Tz Independently any one of the groups Tz-n (n=1-61) shown below:

22. The organic electroluminescent composition according to claim 21, characterized in that: The molecular structure of the main material of the 1,3,5-triazine derivative is shown in the general formula Trz1-A.

23. The organic electroluminescent composition according to claim 21, characterized in that: The weight ratio of the 1,3,5-triazine derivative main material to the carbazole derivative main material and / or the carbazole derivative main material as claimed in any one of claims 15 to 20 is 1:5-5:1; And / or, the main material of the 1,3,5-triazine derivative is any of the following compounds:

24. The organic electroluminescent composition according to claim 23, characterized in that: The weight ratio of the 1,3,5-triazine derivative main material to the carbazole derivative main material and / or the carbazole derivative main material as claimed in any one of claims 15 to 20 is 2:

1.

25. The organic electroluminescent composition according to claim 14, characterized in that: It is any of the following options: Scheme 1: The organic electroluminescent composition comprises 0.3-30.0 parts by weight of any one of the compounds of formulas BN-1R to BN-400R and BN-1S to BN-400S as described in claim 10 and 70-99.7 parts by weight of one or two of the compounds of formulas H-1 to H1-427 as described in claim 20; Scheme 2: The organic electroluminescent composition, which is composed of 3 parts by weight of the boron nitrogen compound as shown in formula I according to any one of claims 1 to 10 and 97 parts by weight of the carbazole derivative host material and / or the carbazole derivative host material according to any one of claims 15 to 20; Scheme 3: The organic electroluminescent composition is composed of 3 parts by weight of the boron nitrogen compound as shown in formula I as described in any one of claims 1 to 10 and 97 parts by weight of a host material; the molecular structure of the host material is a carbazole derivative host material or a carbazole derivative host material as shown in general formula H-1 or H-5 as described in any one of claims 15 to 20; Scheme 4: The organic electroluminescent composition is composed of 3 parts by weight of the boron nitrogen compound as shown in formula I according to any one of claims 1 to 10 and 97 parts by weight of a host material, wherein the host material is Scheme 5: The organic electroluminescent composition comprises 3 parts by weight and 97 parts by weight composition; Scheme 6: The organic electroluminescent composition comprises 3 parts by weight and 97 parts by weight composition; Scheme 7: The organic electroluminescent composition comprises 3 parts by weight and 97 parts by weight composition; Scheme 8: The organic electroluminescent composition comprises 3 parts by weight and 97 parts by weight composition; Scheme 9: The organic electroluminescent composition comprises 0.3-30.0 parts by weight of any one of the boron nitrogen compounds represented by formula I according to any one of claims 1 to 10 and 70-99.7 parts by weight of a host material; the host material is any one of the 1,3,5-triazine derivative host materials represented by formulas TRZ-1 to TRZ-56 according to claim 23, and any one of the carbazole derivative host materials or carbazole derivative host materials represented by formulas H1-1 to H1-427 according to claim 20; the weight ratio of the carbazole derivative host material or carbazole derivative host material to the 1,3,5-triazine derivative host material is 1:5-5:1; Scheme 10: The organic electroluminescent composition comprises 0.3-30.0 parts by weight of any one of the compounds of formulas BN-1R to BN-400R and BN-1S to BN-400S as claimed in claim 10 and 70-99.7 parts by weight of a host material; the host material is any one of the 1,3,5-triazine derivative host materials represented by formulas TRZ-1 to TRZ-56 as claimed in claim 23, and any one of the carbazole derivative host materials or carbazole derivative host materials represented by formulas H1-1 to H1-427 as claimed in claim 20; the weight ratio of the carbazole derivative host material or carbazole derivative host material to the 1,3,5-triazine derivative host material is 1:5-5:1; Scheme 12: The organic electroluminescent composition, which is composed of 3 parts by weight of the boron nitrogen compound as shown in formula I as described in any one of claims 1 to 10 and 97 parts by weight of a host material; the host material is a carbazole derivative host material or a carbazole derivative host material as shown in the general formula H-5 as described in any one of claims 15 to 20, and a 1,3,5-triazine derivative host material as shown in formula TRZ-A as described in claim 21 or 23; the weight ratio of the carbazole derivative host material or the carbazole derivative host material to the 1,3,5-triazine derivative host material is 1:5-5:1; Scheme 13: The organic electroluminescent composition is composed of 3 parts of the boron nitrogen compound shown in Formula I and 97 parts of a host material; the host material is in a weight ratio of 1:2 26. Use of the boron nitrogen compound of formula I as claimed in any one of claims 1 to 10 or the organic electroluminescent composition as claimed in any one of claims 14 to 25 as an organic electroluminescent material, wherein the boron nitrogen compound of formula I is used as a doped luminescent material.

27. A use as claimed in claim 26, wherein the organic electroluminescent composition is used as a light-emitting layer in preparing an organic electroluminescent device.

28. An organic electroluminescent device, comprising an anode, a light-emitting layer, an optional hole injection layer, an optional hole transport layer, an optional electron transport layer, an optional electron injection layer and a cathode; wherein at least one of the light-emitting layer, the electron injection layer, the electron transport layer, the hole transport layer and the hole injection layer comprises the organic electroluminescent composition as described in any one of claims 14 to 26.

29. Use of the organic electroluminescent device according to claim 28 in an organic electroluminescent display or an organic electroluminescent lighting source.

Images