WO2023142486A1 - Boron-nitrogen compound, preparation method therefor, and application thereof - Google Patents

Abstract

Disclosed are a boron-nitrogen compound, a preparation method therefor, and an application thereof. The boron-nitrogen compound has a narrow spectrum and serves as a narrow spectrum light-emitting material used for preparing a light-emitting layer of an organic electroluminescent device; as a consequence, a prepared organic electroluminescent device achieves narrow spectrum TADF emission, and the electroluminescent external quantum efficiency of the device reaches 27% or more.

Description

A kind of boron nitrogen compound and its preparation method and application technical field

The embodiment of the present application relates to the technical field of organic electroluminescence, such as a boron nitrogen compound and its preparation method and application.

Background technique

Organic Optoelectronic Materials (Organic Optoelectronic Materials) is a class of organic materials with the characteristics of photon and electron generation, conversion and transmission. At present, the controllable optoelectronic properties of organic optoelectronic materials have been applied in organic light-emitting diodes (Organic Light-Emitting Diode, OLED), organic solar cells (Organic Photovoltage, OPV), organic field effect transistors (Organic Field Effect Transistor, OFET), and even are organic lasers. In recent years, OLED has become a very popular new flat panel display product at home and abroad. OLED display has the characteristics of self-illumination, wide viewing angle, short response time, high luminous efficiency, wide color gamut, low operating voltage, thin panel, large-size flexible panel can be produced and low cost, and is known as the star of the 21st century Flat display product.

The history of organic electroluminescence can be traced back to the report of Bemanose et al. in 1953 (A.Bemanose, M.Comet, P.Vouaux, Sur un nouveau mode d′émission luminuse chez certains composésorganiques, J.Chim.Phys., 1953 , 50, 64-68), about 10 years later, and in 1963, Pope et al. of New York University applied a voltage on the crystal of anthracene, and the fluorescence emission of anthracene could be observed (M.Pope, H.Kallmann andP.Magnante, Electroluminescence in Organic Crystals, J. Chem. Phys., 1963, 38, 2042). In 1987, CW Tang et al. of Kodak Corporation of the United States used ultra-thin film technology to use aromatic amines with better hole transport effects as the hole transport layer, aluminum complexes of 8-hydroxyquinoline as the light-emitting layer, and indium tin oxide (ITO ) films and metal alloys were used as anode and cathode, respectively, to prepare light-emitting devices. The device obtained a green light emission with a brightness of up to 1000cd/ ^m2 at a driving voltage of 10V, and the efficiency of the device was 1.5lm/W (CWTang and SAVanSlyke, Organic electroluminescent diodes, Appl.Phys.Lett., 1987, 51, 913) , this breakthrough made organic electroluminescence research carried out rapidly and deeply all over the world. In 1990, Burroughes et al. of Cambridge University proposed the first light-emitting diode based on polymer (PPV). It shows that PPV can be used as a highly fluorescent emitting material in single-layer devices, and it has high luminous efficiency (Burroughes JH et al., Light-emitting diodes based on conjugated polymers, Nature, 1990, 347, 539.). In 1998, Baldo and Forrest of Princeton University reported the first phosphorescent device based on electroluminescence, which could have 100% internal quantum yield in principle (MA Baldo, DFO'Briene et al., Highly efficient phosphorescent emission from organic electroluminescent devices , Nature, 1998, 395, 151), but on the one hand, noble metals such as iridium and platinum are generally used as phosphorescent materials, which are expensive; Therefore, it is extremely important to develop an OLED device that uses cheap and stable organic small molecule materials and can achieve high-efficiency light emission.

In 2012, the Adachi research group at Kyushu University reported a highly efficient all-fluorescent OLED device based on the thermally activated delayed fluorescence (TADF) mechanism (Uoyama H, Goushi K, Shizu K, et al.Highly efficient organic light-emittingdiodes from delayed fluorescence, Nature, 2012, 492(7428): 234-238.), when the energy level difference between S1 and T1 of the molecule is small enough, the triplet excitons can absorb thermal energy, return to the singlet state through the RISC process, and then emit fluorescence. The internal quantum efficiency (IQE) can theoretically reach 100%, and the external quantum efficiency (EQE) can even be as high as 30%, comparable to the level of phosphorescent devices. As the next generation of luminescent materials, TADF materials are in the ascendant.

TADF molecules are mainly used as guest materials to achieve high-efficiency thermally activated delayed fluorescence in wide-bandgap host materials (Q. Zhang, J. Li, K. Shizu, et al. Design of Efficient Thermally Activated Delayed Fluorescence Materials for Pure Blue Organic Light Emitting Diodes, J.Am.Chem.Soc.2012, 134, 14706; H.Uoyama, K.Goushi, K.Shizu, H.Nomura, C.Adachi, Highly efficient organic light-emittingdiodes from delayed fluorescence, Nature, 2012, 492, 234; T. Nishimoto, T. Yasuda, et al., Asix-carbazole-decorated cyclophosphazene as a host with high triplet energy to realize efficient delayed-fluorescence OLEDs, Mater. Horiz., 2014, 1, 264). Different from the localized (LE) state emission of traditional fluorescent molecules, the emission of TADF mainly comes from the transition of the ICT state, so it is easily affected by the vibration and rotation motion between donor and acceptor, resulting in a wider spectrum. Although a wider spectrum is beneficial to lighting applications, it cannot meet the requirements of high color purity in the display field. The main purpose of OLED is to display, so the narrow spectrum design of TADF materials (that is, smaller half-maximum width, FWHM) is very necessary.

Contents of the invention

The following is an overview of the topics described in detail in this article. This summary is not intended to limit the scope of the claims.

The embodiment of the present application provides a boron nitrogen compound and its preparation method and application. The compound provided in the embodiment of the present application aims to solve the defects of TADF light-emitting molecules, provide narrow-spectrum light-emitting materials, and construct derivatives of different substituents To adjust the emission wavelength of the emission spectrum. The tetraphenylene-based boron-nitrogen heterocyclic light-emitting compound involved in this application is used as a narrow-spectrum light-emitting material to prepare a light-emitting layer of an organic electroluminescent device, and the organic electroluminescent device thus prepared realizes narrow-spectrum TADF emission.

On the one hand, the embodiment of the present application provides a boron nitrogen compound, the boron nitrogen compound has the structure shown in the following formula I:

R ¹ and R ² are independently H, D (deuterium), fluorine, CN, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, replaced by one or more C6～C18 aryl substituted by R ^a , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R ^a , dianilino, or one or more R ^a substituted diphenylamino group;

R ⁴ is independently H, D (deuterium), fluorine, CN, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, substituted by one or more R ^a C6～C18 aryl, 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R ^a , dianilino, or substituted by one or more R ^a Diphenylamino group;

R ⁵ and R ⁶ are independently H, D (deuterium), C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, 5- to 18-membered heteroaryl ;

Each occurrence of R ^a is independently D (deuterium), fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl, replaced by one or more R C6-C14 aryl substituted by ^b , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R ^b , dianilino, or one or more R ^b Substituted diphenylamino groups;

Each occurrence of R ^b is independently D (deuterium), fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, replaced by one or more R ^C substituted C6~C14 aryl, 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R ^c , dianilino, or one or more R ^c Substituted diphenylamino groups;

Each occurrence of R ^c is independently D (deuterium), fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, replaced by one or more Rd Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R ^d , dianilino, or substituted by one or more R ^d The diphenylamino group;

Each occurrence of R ^d is independently D (deuterium), fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl or substituted by one or more R ^e C6～C14 aryl;

Each occurrence of R ^e is independently D (deuterium), fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, or C6-C14 aryl.

The alkyl, alkoxy, cycloalkyl, aryl, heteroaryl are optionally substituted with one or more substituents selected from the group consisting of: halogen, -CN, C1-C12 alkyl, C1-C12 alkoxy radical, C1-C12 haloalkyl, C2-C6 alkenyl, C3-C10 cycloalkyl, C6-C14 aryl and 5- to 18-membered heteroaryl.

In this application, the "alkyl, alkoxy, cycloalkyl, aryl, heteroaryl optionally substituted with one or more substituents selected from the following" refers to alkyl, alkoxy, Cycloalkyl, aryl, heteroaryl can be unsubstituted alkyl, alkoxy, cycloalkyl, aryl or heteroaryl, also can be substituted alkyl, substituted alkoxy, substituted Cycloalkyl, substituted aryl or substituted heteroaryl, when the group is substituted, its substituent is selected from one or more of the listed groups (halogen, -CN, C1-C12 alkyl, C1-C12 alkoxy, C1-C12 haloalkyl, C2-C6 alkenyl, C3-C10 cycloalkyl, C6-C14 aryl and 5- to 18-membered heteroaryl).

In one embodiment, said R ¹ and R ² are independently H, D (deuterium), fluorine, C1-C12 alkyl, C ₁ -C ₁₂ alkoxy, C ₃ -C ₁₀ cycloalkyl, benzene aryl group, aryl group substituted by at least one C ₁ -C ₁₂ alkyl group, phenyl-C ₁ -C ₁₂ alkyl group, aryl group substituted by at least one C ₁ -C ₁₂ alkoxy group, dianilino group, aryl group substituted by at least one A diphenylamino group substituted by a C ₁ -C ₁₂ alkyl group, a carbazolyl group, a carbazolyl group substituted by at least one C ₁ -C ₁₂ alkyl group.

In one embodiment, each occurrence of R ^a is independently D (deuterium), fluorine, C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ alkoxy, C ₃ -C ₁₀ cycloalkyl, Phenyl substituted by at least one C ₁ -C ₁₂ alkyl group, phenyl-C ₁ -C ₁₂ alkyl group, phenyl group substituted by at least one C ₁ -C ₁₂ alkoxy group, dianilino group, substituted by at least one C ₁ -C ₁₂ alkyl substituted diphenylamino, carbazolyl, carbazolyl substituted by at least one C ₁ -C ₁₂ alkyl.

In one embodiment, each occurrence of R ^b is independently D (deuterium), fluorine, C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ alkoxy, C ₃ -C ₁₀ cycloalkyl, Phenyl substituted by at least one C ₁ -C ₁₂ alkyl group, phenyl-C ₁ -C ₁₂ alkyl group, phenyl group substituted by at least one C ₁ -C ₁₂ alkoxy group, dianilino group, substituted by at least one C ₁ -C ₁₂ alkyl substituted diphenylamino, carbazolyl, carbazolyl substituted by at least one C ₁ -C ₁₂ alkyl.

In one embodiment, each occurrence of R ^c is independently D (deuterium), fluorine, C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ alkoxy, C ₃ -C ₁₀ cycloalkyl, Phenyl substituted by at least one C ₁ -C ₁₂ alkyl group, phenyl-C ₁ -C ₁₂ alkyl group, phenyl group substituted by at least one C ₁ -C ₁₂ alkoxy group, dianilino group, substituted by at least one C ₁ -C ₁₂ alkyl substituted diphenylamino, carbazolyl, carbazolyl substituted by at least one C ₁ -C ₁₂ alkyl.

In one embodiment, each occurrence of R ^d is independently D (deuterium), fluorine, C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ alkoxy, C ₃ -C ₁₀ cycloalkyl, Phenyl substituted by at least one C ₁ -C ₁₂ alkyl, phenyl substituted by at least one C ₁ -C ₁₂ alkoxy, carbazolyl, carbazolyl substituted by at least one C ₁ -C ₁₂ alkyl .

In one embodiment, said R ^{and R} are independently H, D (deuterium), fluoro, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, hexyl, octyl base, decyl,

Methoxy, Ethoxy, Butoxy, Hexyloxy,

Cyclohexyl, adamantyl, phenyl, 4-methyl-phenyl, 4-ethyl-phenyl, 4-propyl-phenyl, 4-isopropylphenyl, 4-n-butylphenyl,

Wherein the wavy line represents the linking site of the group.

In some preferred embodiments, said R ¹ and R ² are independently H, methyl,

phenyl,

Wherein the wavy line represents the linking site of the group.

In some preferred embodiments, the R ¹ and R ² are the same, selected from H, methyl,

phenyl,

any of the

Wherein R ^g is H, methyl, isopropyl, tert-butyl or

In some preferred embodiments, R ⁴ is H, C1～C8 alkyl, C6～C12 aryl, C5～C18 heteroaryl, ^Rf substituted C6～C12 aryl or ^Rf substituted C5～C18 hetero Aryl;

R ^f is D (deuterium), fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, hexyl, octyl, decyl,

Methoxy, Ethoxy, Butoxy, Hexyloxy,

Cyclohexyl, adamantyl, phenyl, 4-methyl-phenyl, 4-ethyl-phenyl, 4-propyl-phenyl, 4-isopropylphenyl, 4-n-butylphenyl,

Wherein the wavy line represents the linking site of the group.

In some preferred embodiments, said R ^f is H, methyl,

phenyl,

Wherein the wavy line represents the linking site of the group.

In some preferred embodiments, the R ⁴ is H, methyl,

phenyl,

R ^h is H, methyl, tert-butyl or

In some preferred embodiments, R ⁵ is H, C1-C8 alkyl, C6-C18 aryl or C5-C18 heteroaryl.

In some preferred embodiments, R ⁶ is H or methyl.

In some embodiments of the present application, the boron nitrogen compound is any one of the following compounds:

On the other hand, the embodiment of the present application provides the preparation method of the above-mentioned boron nitrogen compound, and the preparation method comprises the following steps:

(1) In the presence of a catalyst, compound BN-Bpin reacts with compound B to obtain compound BN-DBTn, and the reaction formula is as follows:

(2) Compound BN-DBTn ring-closing reaction occurs in the presence of ferric chloride, obtains the boron nitrogen compound shown in formula I, and reaction formula is as follows:

Preferably, the molar ratio of compound BN-Bpin to compound B in step (1) is 1:0.8 to 2, such as 1:0.8, 1:1, 1:1.2, 1:1.5, 1:1.8 or 1:2 .

Preferably, the reaction described in step (1) is carried out in the presence of a weakly basic substance;

Preferably, the weakly alkaline substance is potassium carbonate;

Preferably, the catalyst described in step (1) is tetrakis (triphenylphosphine) palladium;

Preferably, the amount of the catalyst in step (1) is 0.1% to 15% of the amount of the compound BN-Bpin, such as 0.2%, 0.5%, 1%, 3%, 5%, 8%, 10%, 12% or 15%.

Preferably, the solvent of the reaction described in step (1) is tetrahydrofuran;

Preferably, the reaction described in step (1) is carried out under reflux;

Preferably, the reaction time in step (1) is 5-24 hours, such as 5 hours, 8 hours, 10 hours, 12 hours, 15 hours, 18 hours, 20 hours, 22 hours or 24 hours.

Preferably, the amount of ferric chloride in step (2) is 3 to 50 times the amount of compound BN-Dpn;

Preferably, the solvent of the ring closure reaction described in step (2) is dichloromethane;

Preferably, the ring closure reaction described in step (2) is carried out at room temperature;

Preferably, the ring closure reaction in step (2) takes 0.5-12 hours, such as 0.5 hours, 1 hour, 3 hours, 5 hours, 8 hours, 10 hours or 12 hours.

Preferably, the reactions in step (1) and step (2) are carried out under nitrogen protection.

On the other hand, the embodiment of the present application provides an organic electroluminescent material, the organic electroluminescent material includes the above-mentioned boron-nitrogen heterocyclic light-emitting compound of triphenylene.

On the other hand, the embodiment of the present application provides an organic electroluminescent device, the organic electroluminescent device comprises an anode and a cathode and an organic thin film layer placed between the anode and the cathode, the organic thin film layer includes a light emitting layer, optional hole injection layer, optional hole transport layer, optional electron transport layer, optional electron injection layer, wherein the light emitting layer, electron injection layer, electron transport layer, hole transport layer 1. At least one of the hole injection layers contains the boron nitride compound as described above.

In the present application, the tetraphenylene-containing borazine ring light-emitting compound having the structure shown in formula I can be used as a functional material for the light-emitting layer, electron injection layer, electron transport layer, spacer, etc. of an organic electroluminescent device. In at least one of the hole transport layer and the hole injection layer.

In one embodiment, the organic electroluminescent device of the present application may further include an optional hole blocking layer, an optional electron blocking layer, an optional capping layer, and the like.

In one embodiment, the organic electroluminescent device has a structure as shown in Figure 1, wherein, 1 is an ITO anode, 2 is a hole injection layer, 3 is a hole transport layer, 4 is a light-emitting layer, and 5 is an electron The transport layer, 6 is the electron injection layer, and 7 is the metal cathode.

In a certain embodiment, the tetraphenylene borazine ring light-emitting compound having the structure shown in formula I is used to prepare a light-emitting layer in an organic electroluminescent device.

In a certain embodiment, the organic electroluminescent device further includes 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 includes the above-mentioned The light emitting layer of the boron nitrogen compound may also include any one or a combination 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.

On the other hand, the embodiment of the present application provides an organic electroluminescent composition, which includes the above-mentioned boron-nitride compound and a host material as a dopant material;

Preferably, the host material is a material having electron transport capability and/or hole transport capability and whose triplet excited state energy is higher than or equal to that of the dopant material.

In a certain embodiment of the present application, the host material in the organic electroluminescent composition is a carbazole-derived compounds and/or carboline derivatives:

Wherein X ₁ , Y ₁ and Z ₁ are CH or N, and at most one of X ₁ , Y ₁ and Z ₁ is N.

Wherein R ^1H and R ^2H are independently any of the following groups:

Wherein X ₁ , Y ₁ and Z ₁ are CH or N, and at most one of X ₁ , Y ₁ and Z ₁ is N;

Where R ^aH and R ^bH are independently H, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, C ₆ -C ₂₀ aryl, C ₁ -C ₂₀ alkyl substituted C ₆ -C ₂₀ An aryl group or a C ₆ -C ₂₀ aryl group substituted by a C ₁ -C ₂₀ alkoxy group, and * represents the connection site of the group.

In a certain embodiment of the present application, the organic electroluminescent composition preferably contains 0.3-30.0 wt% (weight percentage) of the boron- The nitrogen-heterocyclic light-emitting compound is used as a doping material, and the remaining 99.7-70.0 wt% components are host materials composed of 1-2 compounds with structures of formula (H-1) to formula (H-6).

In one embodiment of the present application, the host material contains two compounds having the structures of formula (H-1) to formula (H-6), and the weight ratio of the two compounds is 1:5 to 5:1, For example, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.

In a certain embodiment of the present application, the host material in the organic electroluminescent composition is 1-2 of compounds H1-1 to H1-427.

In a certain embodiment of the present application, the organic electroluminescent composition contains 0.3-30.0 wt% (weight percentage) of the boron-aza of the triphenylene structure shown in formula I as above In the cycloluminescent compound, the remaining 99.7-70.0 wt% components are one or two compounds in compounds H1-1 to H1-427.

In a preferred embodiment of the present application, the organic electroluminescent composition contains two compounds in compounds H1-1 to H1-427 as host materials, and the weight ratio of these two compounds is 1:5 to 5: 1, such as 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.

In a certain embodiment of the present application, the dopant material in the organic electroluminescent composition is any one of the boron-azacyclic luminescent compounds of triphenylene structure shown in formula I (the content is 0.3wt -30.0wt%); the host material (content is 99.7wt-70.0wt%) is any of the compounds shown in formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A One and any one of the compounds having structures shown in formulas H-1 to H-6.

In a preferred embodiment, the compound shown in Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A in the host material is combined with H-1, H-2, H-3 , H-4, H-5 or H-6 The weight ratio between the compounds shown in 1:5 to 5:1, such as 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.

One or two of R ^1a , R ^1b , R ^2a , R ^2b , R ^3a and R ^3b are independently R ^Tz , and the rest are the same or different and independently hydrogen, deuterium, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkoxy, C ₆ -C ₁₈ aryl, C ₁ -C ₈ alkyl substituted C ₆ -C ₁₈ aryl or C ₁ -C ₈ alkoxy substituted C ₆ -C ₁₈ Aryl; R ^Tz is any one of the substituting groups shown in the following formula:

Wherein the asterisk represents the linking site of the group.

In a certain embodiment of the present application, the dopant material in the organic electroluminescent composition is any one of the above-mentioned boron nitrogen compounds with the structure shown in formula I (the content is 0.3wt-30.0 wt%); the host material (content is 99.7wt-70.0wt%) is any one of the compounds shown in formula TRZ-1 to TRZ-76 and carbazole or carboline shown in formula H1-1 to H1-427 any of the derivatives.

In a preferred embodiment, the weight ratio between the compound represented by the formulas TRZ-1 to TRZ-76 and the carbazole or carboline derivative in the host material is 1:5 to 5:1, for example 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.

On the other hand, the embodiment of the present application provides an organic electroluminescent material, and the organic electroluminescent material includes the above-mentioned organic electroluminescent composition.

On the other hand, the embodiment of the present application provides an organic electroluminescent device, the organic electroluminescent device comprises an anode and a cathode and an organic thin film layer placed between the anode and the cathode, the organic thin film layer includes a light emitting layer, optional hole injection layer, optional hole transport layer, optional electron transport layer, optional electron injection layer, wherein the light emitting layer, electron injection layer, electron transport layer, hole transport layer , at least one of the hole injection layers comprises the organic electroluminescent composition as described above.

In the present application, the organic electroluminescent composition can be used as a functional material for at least one of the light-emitting layer, electron injection layer, electron transport layer, hole transport layer, and hole injection layer of an organic electroluminescent device. middle.

In a certain embodiment of the present application, the material of the light-emitting layer in the organic electroluminescent device comprises the above-mentioned organic electroluminescent composition.

In a certain embodiment of the present application, the organic electroluminescent composition is a light-emitting layer, and the light-emitting principle of the light-emitting layer is based on the energy transfer from the host material to any compound shown in formula I or the carrier of the light-emitting material itself capture.

In a certain embodiment of the present application, the organic electroluminescent composition is a light-emitting layer; the host material in the organic electroluminescent composition can be such as formula (H-1) to formula (H-6 ) carbazole derivatives and/or carboline derivatives. In a preferred embodiment, the organic electroluminescent composition contains 0.3-30.0wt% of any compound represented by formula I, and the remaining 99.7-70.0wt% of the ingredients have formulas (H-1) to The main body composed of 1-2 kinds of compounds with the structure of formula (H-6). For example, when the host contains two compounds having structures of formula (H-1) to formula (H-6), the weight ratio of the two compounds is 1:5 to 5:1.

In a certain embodiment of the present application, the organic electroluminescent composition is a light-emitting layer; the host material in the composition is 1-2 of compounds H1-1 to H1-427. In a preferred embodiment, the organic electroluminescent composition contains 0.3-30.0 wt% of any compound represented by formula I or formula II, and the remaining 99.7-70.0 wt% is compound H1-1 to 1-2 compounds in H1-427. For example, when the composition contains two compounds of formulas H1-1 to H1-427, the weight ratio of these two compounds is 1:5 to 5:1.

In a certain embodiment of the present application, the organic electroluminescent composition is a light-emitting layer; the dopant material in the organic electroluminescent composition is any compound shown in formula I (content: 0.3wt-30.0wt%); the host material (content is 99.7wt-70.0wt%) is composed of any one of compounds such as formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A species and any one of the compounds shown in formulas H-1 to H-6. For example, in the host material, Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A compounds are combined with H-1, H-2, H-3, H-4, The weight ratio between the compounds shown in H-5 or H-6 is 1:5 to 5:1.

In a certain embodiment of the present application, the organic electroluminescent composition is a light-emitting layer; the dopant material in the organic electroluminescent composition is any compound shown in formula I (content: 0.3wt-30.0wt%); the host material (content is 99.7wt-70.0wt%) is composed of any one of 1,3,5-triazine derivatives shown in formula TRZ-1 to TRZ-76 and formula H1- Any one of the carbazole or carboline derivatives shown in 1 to H1-427. For example, in the host material, the weight ratio between the 1,3,5-triazine derivative and the carbazole or carboline derivative is 1:5 to 5:1.

In a certain embodiment of the present application, the organic electroluminescent composition is a light-emitting layer; the dopant material in the organic electroluminescent composition is any compound represented by formulas BN1 to BN180 ( Content is 0.3wt-30.0wt%); Host material (content is 99.7wt-70.0wt%) is made up of compounds such as formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, and Trz6-A Any one of them and any one of the carbazole or carboline derivatives shown in formulas H1-1 to H1-427. For example, in the host material, such as formula Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A, and Trz6-A compound with formula H1-1 to H1-427 shown carbazole or carbazole The weight ratio between the morphine derivatives is 1:5 to 5:1.

In a certain embodiment of the present application, the organic electroluminescent device further includes 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 includes The light-emitting layer containing the above-mentioned organic electroluminescent composition may also include any one 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 or A combination of at least two.

On the other hand, the embodiment of the present application provides an application of the organic electroluminescent device in an organic electroluminescent display or an organic electroluminescent lighting source.

Glossary

Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs.

As used herein, the term "comprises" or "includes (comprising)" can be open, semi-closed and closed. In other words, the term also includes "consisting essentially of", or "consisting of".

Group definition

In this specification, groups and substituents thereof can be selected by those skilled in the art to provide stable moieties and compounds. When a substituent is described by a conventional chemical formula written from left to right, the substituent also includes chemically equivalent substituents obtained when the structural formula is written from right to left.

The section headings used in this specification are for the purpose of organizing the article only and should not be construed as limitations on the subject matter described. All documents or portions of documents cited in this application, including but not limited to patents, patent applications, articles, books, manuals, and treatises, are hereby incorporated by reference in their entirety.

Unless defined otherwise, all technical and scientific terms used herein have meanings standard to the art to which the claimed subject matter belongs. In the event that more than one definition exists for a term, the definition herein controls.

It should be understood that as used in this application, a singular form such as "a" includes plural referents unless otherwise specified. In addition, the term "comprising" is an open definition rather than a closed one, that is, it includes the content specified in this application, but does not exclude other content.

Unless otherwise specified, this application adopts traditional methods of mass spectrometry and elemental analysis, and the steps and conditions can refer to the conventional operating steps and conditions in the art.

Unless otherwise indicated, this application employs standard nomenclature and standard laboratory procedures and techniques of analytical chemistry, synthetic organic chemistry and optics. In some cases, standard techniques are used for chemical synthesis, chemical analysis, and performance testing of light-emitting devices.

The compounds of the present application may contain unnatural proportions of atomic isotopes at one or more of the atoms that constitute the compounds. For example, compounds can be labeled with radioactive isotopes, such as deuterium (2H). All changes in isotopic composition of the compounds of the present application, whether radioactive or not, are included within the scope of the present application.

In this application, unless otherwise specified, the number of "substitution" can be one or more; when it is multiple, it means more than two, for example, it can be 2, 3 or 4. Moreover, when the number of the "substitutions" is multiple, the "substitutions" may be the same or different. In the present application, the position of "substitution" can be arbitrary unless otherwise specified.

In this application, the term "alkyl", as a group or part of another group (for example, in a group such as a halogen-substituted alkyl group), is intended to include branched and straight chains having the specified number of carbon atoms. Saturated aliphatic hydrocarbon group. For example, C ₁ -C ₂₀ alkyl includes linear or branched alkyl having 1-20 carbon atoms. As defined in "C ₁ -C ₆ alkyl" includes groups having 1, 2, 3, 4, 5, or 6 carbon atoms in a linear or branched structure. For example, in this application, 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); butyl is C4 alkyl (including isomers, such as n-butyl, sec-butyl, isobutyl or tert-butyl); pentyl is C5 alkyl ( Including isomers such as n-pentyl, 1-methyl-butyl, 1-ethyl-propyl, 2-methyl-1-butyl, 3-methyl-1-butyl, isopentyl base, tert-pentyl or neopentyl); hexyl is C6 alkyl (including isomers such as n-hexyl or isohexyl).

The term "alkoxy" as used herein refers to an alkyl group as defined above linked via an oxygen bond (-O-), respectively.

In this application, as a group or part of other groups, the term "Cn-m aryl" refers to a monocyclic or polycyclic aromatic group with n to m ring carbon atoms (the ring atoms are only carbon atom) having at least one carbocyclic ring with a conjugated π-electron system. Examples of the aforementioned aryl unit include phenyl, naphthyl, indenyl, azulenyl, fluorenyl, phenanthrenyl, or anthracenyl. In one embodiment, the aryl group is preferably a C6-14 aryl group, such as phenyl and naphthyl, more preferably phenyl.

In this application, the term "n-m membered heteroaryl", as a group or part of another group, means that the ring atoms contain one or more (for example, 1, 2, 3 and 4) selected from nitrogen, oxygen and sulfur The heteroatom aromatic group has n to m ring atoms, and the heteroaryl group is a monocyclic, bicyclic, tricyclic or tetracyclic ring system, wherein at least one ring is an aromatic ring. Heteroaryl groups within the scope of this definition include, but are not limited to: acridinyl, carbazolyl, cinnolinyl, quinoxalinyl, pyrazolyl, indolyl, benzotriazolyl, furyl, thienyl , benzothienyl, benzofuryl, quinolinyl, isoquinolyl, oxazolyl, isoxazolyl, pyrazinyl, pyridazinyl, pyridyl, pyrimidinyl, pyrrolyl, tetrahydroquinoline , imidazolyl, triazolyl, tetrazolyl, thiazolyl, isothiazolyl, furazanyl, thiadiazolyl, oxadiazolyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl , purinyl, pteridyl, naphthyridyl, quinazolinyl, phthalazinyl, imidazopyridyl, imidazothiazolyl, imidazooxazolyl, benzothiazolyl, benzoxazolyl, benzo Imidazolyl, isoindolyl, indazolyl, pyrrolopyridyl, thienopyridyl, furopyridyl, benzothiadiazolyl, benzoxadiazolyl, pyrrolopyrimidinyl, thienofuryl . In one embodiment, as preferred examples of "5- to 18-membered heteroaryl", furyl, thienyl, pyrrolyl, imidazolyl, thiazolyl, pyrazolyl, oxazolyl, isoxazolyl , isothiazolyl, pyridyl, pyrimidinyl and carbazolyl, more preferably carbazolyl.

The term Cn-Cm cycloalkyl as used herein refers to a monocyclic or polycyclic alkyl group having n to m carbon atoms, such as 3-C10 cycloalkyl and C3-C6 cycloalkyl. Examples include adamantyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and bicycloheptyl. In one embodiment, the C3-C10 cycloalkyl is preferably adamantyl or cyclohexyl.

The limited carbon number range of the group described in this application means any integer number of carbon atoms included in the limited range, for example, C ₁ to C ₂₀ means that the carbon number of the group can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20, _C3 - _C10 refers to the group The number of carbon atoms in the group can be 3, 4, 5, 6, 7, 8, 9 or 10, and the limited carbon number range of other groups can be analogized.

On the basis of not violating common knowledge in the field, the above-mentioned preferred conditions can be combined arbitrarily to obtain the preferred examples of the present application.

The reagents and raw materials used in this application are all commercially available.

Compared with related technologies, the embodiments of the present application have the following beneficial effects:

The boron nitrogen compound of the embodiment of the present application adopts the strategy of expanding the conjugation degree of the core resonance unit to realize the effective red shift of the spectrum of the BN derivative. The boron nitrogen compound containing tetraphenylene in the embodiment of the present application has a narrow spectrum and is used as a narrow spectrum luminescent material The method is used to prepare the light-emitting layer of the organic electroluminescent device, and the organic electroluminescent device thus prepared realizes narrow-spectrum TADF emission, and makes the electroluminescent external quantum efficiency of the device as high as 24% or more.

Other aspects will be apparent to others upon reading and understanding the drawings and detailed description.

Description of drawings

The accompanying drawings are used to provide a further understanding of the technical solutions herein, and constitute a part of the description, and are used together with the embodiments of the application to explain the technical solutions herein, and do not constitute limitations to the technical solutions herein.

Fig. 1 is a schematic structural view of an organic electroluminescent device provided in an embodiment of the present application, wherein 1 is an ITO anode, 2 is a hole injection layer, 3 is a hole transport layer, 4 is a light-emitting layer, 5 is an electron transport layer, 6 7 is the electron injection layer, and 7 is the metal cathode.

Fig. 2 is the photoluminescence spectrum of compound BN31 in toluene solution (concentration: 1×10 ^-5 M).

Figure 3 is the electroluminescence spectrum of compound BN31.

Detailed ways

The technical solutions of the present application will be further described below through specific implementation methods. It should be clear to those skilled in the art that the embodiments are only for helping to understand the present application, and should not be regarded as a specific limitation on the present application.

In the examples of the present application, the raw materials utilized for the synthesis of the shown compounds are as follows:

The specific raw materials BXX used are as follows

The present application is further described below by means of representative embodiments, but the present application is not therefore limited to the scope of the described embodiments. For the experimental methods that do not specify specific conditions in the following examples, select according to conventional methods and conditions, or according to the product instructions.

The synthetic basic process route of the compound involved in this application is as follows:

Using BN-Bpin as the substrate, the precursor was firstly obtained by a simple one-step Suzuki reaction and the coupling of monobromobiphenyl compounds containing (not) various substituents, and then obtained by a one-step classical reaction in the presence of ferric chloride. Scholl oxidative coupling gave the final product. Concrete synthetic process step is:

The first step, 2'-iodo-1,1':3',1'-triphenyl compound (B1-B15) (0.6mmol), 383mg BN-Bpin (0.5mmol), 0.14g potassium carbonate ( 1 mmol) and water (2 mL) were added to tetrahydrofuran (16 mL), the mixture was bubbled with nitrogen for 10 minutes, and 28.9 mg tetrakis(triphenylphosphine)palladium (0.025 mmol) was added under high flow of 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 spin-dried under vacuum, and then purified by column chromatography to obtain the precursor BN-DBTn (n=1-180).

In the second step, 0.3mmol BN-DBTn(A1-A12) was dissolved in 50mL ultra-dry dichloromethane, and 1.12g ferric chloride was dissolved in 10mL nitromethane. Liquid nitrogen degassing replacement 30min. The nitromethane mixture was slowly added dropwise in an ice-water bath, and then slowly raised to room temperature, and the reaction was continued for 2 h. The reaction was quenched by adding 5 mL of methanol and 5 mL of water, the reaction mixture was extracted with dichloromethane and water, the organic phase was heated and spin-dried under vacuum, and then purified by column chromatography to obtain the target product BNn (n=1-180). The relevant data of the target compounds obtained are shown in Table 1.

Taking compound BN31 as an example to illustrate the specific details of the synthesis example experiment:

In the first step, 214mg 2'-iodine-1, 1': 3', 1'-triphenyl compound (0.6mmol), 383mg BN-Bpin (0.5mmol), 0.14g potassium carbonate (1mmol) and water ( 2 mL) was added to tetrahydrofuran (16 mL), the mixture was bubbled with nitrogen for 10 minutes, and 28.9 mg tetrakis(triphenylphosphine)palladium (0.025 mmol) was added under high flow of 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 spin-dried under vacuum, and then purified by column chromatography to obtain the precursor BN-DPT31.

In the second step, 260mg BN-DPT31 (0.3mmol) was dissolved in 50mL ultra-dry dichloromethane, and 1.12g ferric chloride was dissolved in 10mL nitromethane. Liquid nitrogen degassing replacement 30min. The nitromethane mixture was slowly added dropwise in an ice-water bath, and then slowly raised to room temperature, and the reaction was continued for 2 h. The reaction was quenched by adding 5 mL of methanol and 5 mL of water, the reaction mixture was extracted with dichloromethane and water, the organic phase was heated and spin-dried under vacuum, and then purified by column chromatography to obtain the target product BN31.

For the characterization of the product, the testing instrument used for elemental analysis is Vario Micro Cube from Agilent Company of the United States, and the types of testing elements are: C, H, N, S. The instrument used in the mass spectrometry test is the American Thenno Fisher TSQ Endura ultra-high performance liquid chromatography tandem triple quadrupole mass spectrometer.

Table 1. Synthesis Example Product Data Summary

compound	raw material-1	raw material-2	molecular weight	Elemental analysis (%) (C, H, N)	Yield(%)
BN1	A1	B1	640.52	C, 90.00; H, 3.91; N, 4.37	35
BN2	A1	B2	668.63	C, 89.82; H, 4.35; N, 4.19	37
BN3	A1	B3	668.61	C, 89.81; H, 4.37; N, 4.22	40
BN4	A1	B4	696.66	C, 89.65; H, 4.77; N, 4.02	37
BN5	A1	B5	724.71	C, 89.50; H, 5.13; N, 3.82	36
BN6	A1	B6	724.75	C, 89.52; H, 5.15; N, 3.87	37
BN7	A1	B7	758.73	C, 90.23; H, 4.65; N, 3.69	33
BN8	A1	B8	786.77	C, 90.07; H, 5.00; N, 3.58	32
BN9	A1	B9	786.79	C, 90.04; H, 5.02; N, 3.56	36
BN10	A1	B10	807.76	C, 89.22; H, 4.22; N, 5.20	30
BN11	A1	B11	919.97	C, 88.78; H, 5.45; N, 4.57	34
BN12	A1	B12	1044.10	C, 89.73; H, 5.20; N, 4.02	35
BN13	A1	B13	805.74	C, 89.44; H, 4.02; N, 5.25	37
BN14	A1	B14	917.93	C, 88.97; H, 5.25; N, 4.58	30
BN15	A1	B15	1042.11	C, 89.90; H, 5.05; N, 4.03	31
BN16	A2	B1	696.63	C, 89.63; H, 4.75; N, 4.02	30
BN17	A2	B2	724.74	C, 89.50; H, 5.12; N, 3.87	34
BN18	A2	B3	724.71	C, 89.52; H, 5.15; N, 3.88	36
BN19	A2	B4	752.72	C, 89.35; H, 5.49; N, 3.72	38
BN20	A2	B5	780.82	C, 89.22; H, 5.83; N, 3.59	33
BN21	A2	B6	780.80	C, 89.25; H, 5.81; N, 3.57	35
BN22	A2	B7	814.84	C, 89.92; H, 5.32; N, 3.44	37
BN23	A2	B8	842.89	C, 89.77; H, 5.68; N, 3.29	30
BN24	A2	B9	842.87	C, 89.79; H, 5.62; N, 3.32	31
BN25	A2	B10	863.87	C, 88.97; H, 4.92; N, 4.88	30
BN26	A2	B11	976.08	C, 88.63; H, 5.95; N, 4.31	34
BN27	A2	B12	1100.22	C, 89.52; H, 5.68; N, 3.82	36
BN28	A2	B13	861.85	C, 89.19; H, 4.68; N, 4.88	38
BN29	A2	B14	974.07	C, 88.78; H, 5.80; N, 4.31	35
BN30	A2	B15	1098.2	C, 89.68; H, 5.51; N, 3.83	37
BN31	A3	B1	864.98	C, 88.87; H, 6.64; N, 3.24	30
BN32	A3	B2	893.03	C, 88.79; H, 6.89; N, 3.14	31
BN33	A3	B3	893.05	C, 88.77; H, 6.92; N, 3.18	30
BN34	A3	B4	921.09	C, 88.67; H, 7.11; N, 3.04	34
BN35	A3	B5	949.14	C, 88.55; H, 7.33; N, 2.97	36
BN36	A3	B6	949.17	C, 88.58; H, 7.38; N, 2.95	38
BN37	A3	B7	983.16	C, 89.18; H, 6.87; N, 2.85	35
BN38	A3	B8	1011.28	C, 89.03; H, 7.08; N, 2.79	37
BN39	A3	B9	1011.21	C, 89.08; H, 7.07; N, 2.77	30
BN40	A3	B10	1032.19	C, 88.44; H, 6.45; N, 4.07	31
BN41	A3	B11	1144.41	C, 88.16; H, 7.22; N, 3.67	30
BN42	A3	B12	1268.55	C, 89.00; H, 6.83; N, 3.31	34
BN43	A3	B13	1030.17	C, 88.61; H, 6.26; N, 4.08	36
BN44	A3	B14	1142.39	C, 88.32; H, 7.06; N, 3.68	38
BN45	A3	B15	1266.54	C, 89.14; H, 6.69; N, 3.32	33
BN46	A4	B1	944.94	C, 91.52; H, 4.37; N, 2.96	35
BN47	A4	B2	972.99	C, 91.35; H, 4.69; N, 2.84	37

BN48	A4	B3	972.95	C, 91.37; H, 4.66; N, 2.88	30
BN49	A4	B4	1001.05	C, 91.19; H, 4.93; N, 2.80	31
BN50	A4	B5	1029.15	C, 91.08; H, 5.19; N, 2.74	30
BN51	A4	B6	1029.10	C, 91.04; H, 5.20; N, 2.72	34
BN52	A4	B7	1063.12	C, 91.51; H, 4.84; N, 2.64	36
BN53	A4	B8	1091.19	C, 91.36; H, 5.09; N, 2.57	38
BN54	A4	B9	1091.18	C, 91.38; H, 5.08; N, 2.59	33
BN55	A4	B10	1112.16	C, 90.72; H, 4.53; N, 3.78	35
BN56	A4	B11	1224.37	C, 90.25; H, 5.43; N, 3.43	37
BN57	A4	B12	1348.51	C, 90.85; H, 5.23; N, 3.12	30
BN58	A4	B13	1110.14	C, 90.88; H, 4.36; N, 3.79	31
BN59	A4	B14	1222.36	C, 90.40; H, 5.28; N, 3.44	30
BN60	A4	B15	1346.50	C, 90.99; H, 5.09; N, 3.12	34
BN61	A5	B1	1113.27	C, 90.63; H, 5.89; N, 2.52	36
BN62	A5	B2	1141.32	C, 90.55; H, 6.09; N, 2.47	38
BN63	A5	B3	1141.37	C, 90.50; H, 6.13; N, 2.45	35
BN64	A5	B4	1169.38	C, 90.39; H, 6.29; N, 2.40	37
BN65	A5	B5	1197.48	C, 90.28; H, 6.52; N, 2.34	30
BN66	A5	B6	1197.43	C, 90.29; H, 6.48; N, 2.37	31
BN67	A5	B7	1244.47	C, 90.72; H, 6.16; N, 2.25	30
BN68	A5	B8	1259.52	C, 90.60; H, 6.33; N, 2.23	34
BN69	A5	B9	1259.50	C, 90.68; H, 6.32; N, 2.27	36
BN70	A5	B10	1280.48	C, 90.05; H, 5.83; N, 3.28	38
BN71	A5	B11	1392.70	C, 89.69; H, 6.51; N, 3.02	35
BN72	A5	B12	1516.84	C, 90.27; H, 6.25; N, 2.77	37
BN73	A5	B13	1278.46	C, 90.19; H, 5.68; N, 3.29	30
BN74	A5	B14	1390.68	C, 89.82; H, 6.38; N, 3.02	31
BN75	A5	B15	1514.82	C, 90.39; H, 6.12; N, 2.77	30
BN76	A6	B1	1169.38	C, 90.39; H, 6.29; N, 2.40	34
BN77	A6	B2	1197.48	C, 90.29; H, 6.48; N, 2.36	36
BN78	A6	B3	1197.43	C, 90.28; H, 6.47; N, 2.34	38
BN79	A6	B4	1225.48	C, 90.17; H, 6.66; N, 2.29	31
BN80	A6	B5	1253.57	C, 90.09; H, 6.84; N, 2.27	30
BN81	A6	B6	1253.54	C, 90.07; H, 6.85; N, 2.23	34
BN82	A6	B7	1287.56	C, 90.49; H, 6.50; N, 2.18	36
BN83	A6	B8	1315.65	C, 90.42; H, 6.67; N, 2.10	38
BN84	A6	B9	1315.61	C, 90.38; H, 6.70; N, 2.13	33
BN85	A6	B10	1336.59	C, 89.86; H, 6.18; N, 3.14	35
BN86	A6	B11	1448.80	C, 89.54; H, 6.82; N, 2.90	37
BN87	A6	B12	1572.95	C, 90.10; H, 6.54; N, 2.67	30
BN88	A6	B13	1334.57	C, 90.00; H, 6.04; N, 3.15	31
BN89	A6	B14	1446.79	C, 89.66; H, 6.69; N, 2.90	30
BN90	A6	B15	1570.93	C, 90.22; H, 6.42; N, 2.67	34
BN91	A7	B1	1309.40	C, 88.06; H, 4.70; N, 6.42	36
BN92	A7	B2	1337.47	C, 88.02; H, 4.90; N, 6.30	38
BN93	A7	B3	1337.45	C, 88.01; H, 4.93; N, 6.28	35
BN94	A7	B4	1365.50	C, 87.96; H, 5.09; N, 6.15	37
BN95	A7	B5	1393.55	C, 87.91; H, 5.32; N, 6.03	30
BN96	A7	B6	1393.56	C, 87.89; H, 5.28; N, 6.07	31
BN97	A7	B7	1427.58	C, 88.34; H, 5.01; N, 5.89	30
BN98	A7	B8	1455.68	C, 88.29; H, 5.22N, 5.79	34
BN99	A7	B9	1455.63	C, 88.30; H, 5.19; N, 5.77	36
BN100	A7	B10	1476.61	C, 87.85; H, 4.78; N, 6.64	38
BN101	A7	B11	1588.82	C, 87.69; H, 5.46; N, 6.17	35
BN102	A7	B12	1712.97	C, 88.35; H, 5.30; N, 5.72	37
BN103	A7	B13	1474.59	C, 87.97; H, 4.65; N, 6.65	30

BN104	A7	B14	1586.81	C, 87.80; H, 5.34; N, 6.18	31
BN105	A7	B15	1710.95	C, 88.45; H, 5.18; N, 5.73	30
BN106	A8	B1	1758.26	C, 87.44; H, 7.17; N, 4.78	34
BN107	A8	B2	1786.38	C, 87.43; H, 7.28; N, 4.75	36
BN108	A8	B3	1786.35	C, 87.41; H, 7.29; N, 4.70	38
BN109	A8	B4	1814.37	C, 87.38; H, 7.39; N, 4.63	33
BN110	A8	B5	1842.45	C, 87.36; H, 7.58; N, 4.58	35
BN111	A8	B6	1842.42	C, 87.38; H, 7.50; N, 4.56	37
BN112	A8	B7	1876.44	C, 88.35; H, 5.30; N, 5.72	30
BN113	A8	B8	1904.49	C, 87.66; H, 7.37; N, 4.41	31
BN114	A8	B9	1904.52	C, 87.68; H, 7.36; N, 4.43	30
BN115	A8	B10	1925.47	C, 87.33; H, 7.02; N, 5.09	34
BN116	A8	B11	2037.69	C, 87.24; H, 7.42; N, 4.81	36
BN117	A8	B12	2161.83	C, 87.78; H, 7.18; N, 4.54	38
BN118	A8	B13	1923.45	C, 87.42; H, 6.92; N, 5.10	35
BN119	A8	B14	2035.67	C, 87.32; H, 7.33; N, 4.82	37
BN120	A8	B15	2159.81	C, 87.87; H, 7.09; N, 4.54	30
BN121	A9	B1	1301.33	C, 88.61; H, 4.11; N, 6.46	35
BN122	A9	B2	1329.42	C, 88.58; H, 4.32; N, 6.37	37
BN123	A9	B3	1329.39	C, 88.54; H, 4.35; N, 6.32	30
BN124	A9	B4	1357.44	C, 88.48; H, 4.53; N, 6.19	31
BN125	A9	B5	1385.49	C, 88.45; H, 4.73; N, 6.11	30
BN126	A9	B6	1385.52	C, 88.42; H, 4.70; N, 6.07	34
BN127	A9	B7	1419.51	C, 88.84; H, 4.47; N, 5.92	36
BN128	A9	B8	1447.57	C, 88.77; H, 4.67; N, 5.83	38
BN129	A9	B9	1447.59	C, 88.78; H, 4.72; N, 5.81	35
BN130	A9	B10	1468.54	C, 88.33; H, 4.26; N, 6.68	37
BN131	A9	B11	1608.85	C, 88.10; H, 5.12; N, 6.09	30
BN132	A9	B12	1608.81	C, 88.17; H, 5.14; N, 6.12	31
BN133	A9	B13	1466.53	C, 88.45; H, 4.12; N, 6.69	30
BN134	A9	B14	1578.74	C, 88.25; H, 4.85; N, 6.21	34
BN135	A9	B15	1702.88	C, 88.87; H, 4.74; N, 5.76	36
BN136	A10	B1	1750.20	C, 87.84; H, 6.74; N, 4.80	38
BN137	A10	B2	1778.27	C, 87.83; H, 6.87; N, 4.73	31
BN138	A10	B3	1778.25	C, 87.81; H, 6.86; N, 4.75	30
BN139	A10	B4	1806.30	C, 87.77; H, 6.98; N, 4.65	34
BN140	A10	B5	1834.36	C, 87.74; H, 7.11; N, 4.58	36
BN141	A10	B6	1834.39	C, 87.77; H, 7.09; N, 4.63	38
BN142	A10	B7	1868.38	C, 88.07; H, 6.85; N, 4.50	33
BN143	A10	B8	1896.43	C, 88.04; H, 6.72; N, 4.43	35
BN144	A10	B9	1896.45	C, 88.06; H, 6.96; N, 4.48	37
BN145	A10	B10	1917.41	C, 87.70; H, 6.62; N, 5.11	30
BN146	A10	B11	2029.62	C, 87.58; H, 7.05; N, 4.83	31
BN147	A10	B12	2153.76	C, 88.11; H, 6.83; N, 4.55	30
BN148	A10	B13	1915.39	C, 87.79; H, 6.53; N, 5.12	34
BN149	A10	B14	2027.61	C, 87.67; H, 6.96; N, 4.84	36
BN150	A10	B15	2151.75	C, 88.20; H, 6.75; N, 4.56	38
BN151	A11	B1	2254.83	C, 89.49; H, 6.30; N, 3.73	34
BN152	A11	B2	2282.88	C, 89.44; H, 6.40; N, 3.68	36
BN153	A11	B3	2282.88	C, 89.44; H, 6.40; N, 3.68	38
BN154	A11	B4	2310.94	C, 89.40; H, 6.50; N, 3.64	35
BN155	A11	B5	2338.95	C, 89.38; H, 6.59; N, 3.68	37
BN156	A11	B6	2339.03	C, 89.35; H, 6.62; N, 3.59	30
BN157	A11	B7	2373.01	C, 89.59; H, 6.41; N, 3.54	36
BN158	A11	B8	2401.09	C, 89.57; H, 6.51; N, 3.55	35
BN159	A11	B9	2401.06	C, 89.54; H, 6.53; N, 3.50	37

BN160	A11	B10	2422.04	C, 89.26; H, 6.24; N, 4.05	30
BN161	A11	B11	2534.26	C, 89.10; H, 6.60; N, 3.87	31
BN162	A11	B12	2658.40	C, 89.46; H, 6.45; N, 3.69	30
BN163	A11	B13	2420.02	C, 89.34; H, 6.16; N, 4.05	34
BN164	A11	B14	2532.24	C, 89.17; H, 6.53; N, 3.87	36
BN165	A11	B15	2656.38	C, 89.53; H, 6.37; N, 3.69	38
BN166	A12	B1	2246.76	C, 89.81; H, 5.97; N, 3.74	31
BN167	A12	B2	2274.85	C, 89.78; H, 6.07; N, 3.73	30
BN168	A12	B3	2274.83	C, 89.76; H, 6.09; N, 3.69	34
BN169	A12	B4	2302.87	C, 89.71; H, 6.17; N, 3.65	36
BN170	A12	B5	2330.95	C, 89.68; H, 6.27; N, 3.63	38
BN171	A12	B6	2330.93	C, 89.66; H, 6.29; N, 3.61	33
BN172	A12	B7	2364.94	C, 89.89; H, 6.10; N, 3.55	35
BN173	A12	B8	2393.05	C, 89.88; H, 6.19; N, 3.53	37
BN174	A12	B9	2393.00	C, 89.84; H, 6.21; N, 3.51	30
BN175	A12	B10	2413.98	C, 89.56; H, 5.93; N, 4.06	31
BN176	A12	B11	2526.19	C, 89.39; H, 6.30; N, 3.88	30
BN177	A12	B12	2650.33	C, 89.73; H, 6.16; N, 3.70	34
BN178	A12	B13	2411.96	C, 89.64; H, 5.85; N, 4.07	36
BN179	A12	B14	2524.18	C, 89.46; H, 6.23; N, 3.88	38
BN180	A12	B15	2648.32	C, 89.80; H, 6.09; N, 3.70	34

Examples of electroluminescent devices

Some representative electroluminescent device embodiments are given below, and the molecular structures of some materials involved in the device embodiments are as follows:

The following uses the material of the present application to prepare an embodiment of an electroluminescent device, and the specific device preparation process is as follows:

(1) Substrate treatment: transparent ITO glass is used as the base material for preparing devices, and then ultrasonically treated with 5% ITO lotion for 30 minutes, followed by distilled water (2 times), acetone (2 times), isopropanol (2 times) ) ultrasonically, and finally the ITO glass was preserved in isopropanol. Before each use, carefully wipe the surface of the ITO glass with acetone cotton ball and isopropanol cotton ball, rinse with isopropanol and dry, then treat with plasma for 5 minutes for later use. The preparation of the device is completed by the combination of spin coating and vacuum evaporation process.

(2) Preparation of hole injection laminated hole transport layer: first spin-coat a layer of PEDOT with a thickness of 20 nm on the ITO surface: PSS (poly 3,4-ethylenedioxythiophene): polystyrene sulfonate, The material is purchased from Heraeus, Germany and directly used) as the hole injection layer, then spin-coated 50nm thick Poly-HTL on the hole injection layer as the hole transport layer, and then the hole injection layer and the hole transport layer will be The ITO glass was placed in a nitrogen-protected glove box and annealed at 200°C for 30 minutes (to make Poly-HTL crosslink).

(3) Preparation of luminescent layer: Dissolve the host material and luminescent material in xylene at a ratio of 97wt%: 3wt% (wt% is the concentration by weight percentage) to prepare a solution with a concentration of 2wt%, and use the prepared solution to emit by spin coating. A light-emitting layer was prepared, and the thickness of the light-emitting layer was 50 nm.

(4) Preparation of electron transport layer, electron injection layer and metal electrodes: The electron transport layer, electron injection layer and metal electrodes are prepared by evaporation process, and start when the vacuum degree of the vacuum evaporation system reaches below 5×10 ^-4 Pa Evaporation, the deposition rate is determined by the Sainz film thickness meter, and the organic electron transport layer, the LiF electron injection layer and the metal Al electrode are sequentially deposited on the light-emitting layer by using a vacuum evaporation process (see the following effect examples for the specific device structure). where the deposition rate of the organic material is

The deposition rate of LiF is

The deposition rate of Al is

Device Examples A1-A108

In the organic electroluminescent device (structure shown in Figure 1) in the device embodiment A1-A108, PEDOT:PSS is used as the hole injection layer, Poly-HTL is used as the hole transport layer, in the light emitting layer H1- 48 is used as a host material, BN-1 to BN-618 are used as doped luminescent materials (doping concentration is 2wt%), TmPyPB is used as an electron transport material, LiF is used as an electron injection layer, and Al is used as a metal cathode . Effect Examples The structure of the organic electroluminescent device is [ITO/PEDOT:PSS (20nm)/Poly-HTL (50nm)//H1-33+3wt%BNn/TRZ-8 (50nm)/LiF (1nm)/Al( 100nm)].

The current, voltage, luminance, luminescence spectrum and other characteristics of the device are tested synchronously by Photo Research PR 655 spectral scanning luminance meter and Keithley K 2400 digital source meter system. The performance test of the device was carried out at room temperature and ambient atmosphere. The external quantum efficiency (EQE) of the device is calculated according to the current density, luminance and electroluminescence spectrum combined with the visible function under the condition that the luminescence is a Lambertian distribution.

The test results are shown in Table 2.

Table 2

The implementation data of the electroluminescent device effect listed in Table 2 proves that the luminescent material provided by the application can be used to prepare high-efficiency organic electroluminescent devices, and the electroluminescent spectrum has narrow band characteristics, half of the electroluminescent spectrum The peak width is less than or equal to 56 nm, and the electroluminescent external quantum efficiency is as high as 27%.

And the photoluminescence spectrum (i.e. fluorescence spectrum, measured by FLS980 fluorescence spectrometer, excitation wavelength is 365nm) of compound BN31 in toluene solution (concentration: 1×10 ^-5 M) is shown in Figure 2, as can be seen from Figure 2, The luminescence peak is at 560nm, and the half-maximum width is 52nm.

Figure 3 is the electroluminescence spectrum of compound BN31 (tested by Photo Research PR 655 spectral scanning luminance meter), as can be seen from Figure 3, its luminescence peak position is 559nm, and the half-peak width is 48nm.

Device Examples B1-B108

In the organic electroluminescent device in the device example B1-B108, in the organic electroluminescent device in the effect example 2 (structure shown in Figure 1), PEDOT:PSS is used as the hole injection layer, Poly- HTL is used as a hole transport layer, a mixture of H1-33 and TRZ-8 is used as a host material in the light-emitting layer (the weight mixing ratio of H1-33 and TRZ-8 is 1:1), and BNn is used as a doped light-emitting material respectively. (doping concentration is 3wt%), TRZ-8 is used as an electron transport material, LiF is used as an electron injection layer, and Al is used as a metal cathode. Effect Examples The organic electroluminescence device structure is [ITO/PEDOT:PSS (20nm)/Poly-HTL (50nm)/H1-33:TRZ-8+3wt%BNn/TRZ-8 (50nm)/LiF (1nm) /Al(100nm)].

The effect of the device was also tested, the peak position and half-peak width of the electroluminescence spectrum, and the external quantum efficiency of the electroluminescence were tested. The test results are shown in Table 3.

table 3

The implementation data of the electroluminescent device effect listed in Table 3 proves that the luminescent material provided by the application can be used to prepare high-efficiency organic electroluminescent devices, and the electroluminescent spectrum has narrow band characteristics, half of the electroluminescent spectrum The peak width is less than or equal to 55nm, and the electroluminescence external quantum efficiency is as high as more than 27%.

The applicant declares that the present application illustrates the boron nitrogen compound of the present application and its application through the above examples, but the present application is not limited to the above examples, that is, it does not mean that the application must rely on the above examples to be implemented. Those skilled in the art should understand that any improvement to the present application, the equivalent replacement of the raw materials selected in the present application, the addition of auxiliary components, the selection of specific methods, etc., all fall within the scope of protection and disclosure of the present application.

Claims (15)

1. A boron nitrogen compound, wherein, the boron nitrogen compound has the structure shown in the following formula I:

   

   ^R1 and ^R2 are independently H, deuterium, fluorine, CN, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, substituted by one or more R ^a C6～C18 aryl, 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R ^a , dianilino, or substituted by one or more R ^a Diphenylamino group;

   ^R4 is independently H, deuterium, fluorine, CN, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, C6-C substituted by one or more R ^a C18 aryl, 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R ^a , diphenylamino, or diphenylamino substituted by one or more R ^a ;

   R ⁵ and R ⁶ are independently H, deuterium, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, 5- to 18-membered heteroaryl;

   Each occurrence of R ^a is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl, substituted by one or more R ^b C6～C14 aryl, 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R ^b , dianilino, or diphenylamino substituted by one or more R ^b Anilino;

   Each occurrence of R ^b is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, substituted by one or more R ^c C6～C14 aryl, 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R ^c , dianilino, or diphenylamino substituted by one or more R ^c Anilino;

   Each occurrence of R ^c is independently deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, C6 substituted by one or more Rd ~C14 aryl, 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more ^Rd , dianilino, or diphenylamine substituted by one or more ^Rd base;

   Each occurrence of R ^d is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl or C6-C14 substituted by one or more R ^e C14 aryl;

   Each occurrence of R ^e is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, or C6-C14 aryl;

   The alkyl, alkoxy, cycloalkyl, aryl, heteroaryl are optionally substituted with one or more substituents selected from the group consisting of: halogen, -CN, C1-C12 alkyl, C1-C12 alkoxy radical, C1-C12 haloalkyl, C2-C6 alkenyl, C3-C10 cycloalkyl, C6-C14 aryl and 5- to 18-membered heteroaryl.
2. The boron nitrogen compound according to claim 1, wherein said R ¹ and R ² are independently H, deuterium, fluorine, C1-C12 alkyl, C ₁ -C ₁₂ alkoxy, C ₃ -C ₁₀ ring Alkyl, phenyl, aryl substituted by at least one C ₁ -C ₁₂ alkyl, phenyl-C ₁ -C ₁₂ alkyl, aryl substituted by at least one C ₁ -C ₁₂ alkoxy, diphenylamine group, diphenylamino group substituted by at least one C ₁ -C ₁₂ alkyl group, carbazolyl group, carbazolyl group substituted by at least one C ₁ -C ₁₂ alkyl group.
3. The boron nitrogen compound according to claim 1 or 2, wherein each occurrence of R ^a is independently deuterium, fluorine, C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ alkoxy, C ₃ - C ₁₀ cycloalkyl, phenyl substituted by at least one C ₁ -C ₁₂ alkyl, phenyl-C ₁ -C ₁₂ alkyl, phenyl substituted by at least one C ₁ -C ₁₂ alkoxy, diphenylamine group, diphenylamino group substituted by at least one C ₁ -C ₁₂ alkyl group, carbazolyl group, carbazolyl group substituted by at least one C ₁ -C ₁₂ alkyl group.
4. The boron-nitrogen compound according to any one of claims 1-3, wherein each occurrence of said R ^b is independently deuterium, fluorine, C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ alkoxy, C ₃ -C ₁₀ cycloalkyl, phenyl substituted by at least one C ₁ -C ₁₂ alkyl, phenyl-C ₁ -C ₁₂ alkyl, phenyl substituted by at least one C ₁ -C ₁₂ alkoxy , diphenylamino, diphenylamino substituted by at least one C ₁ -C ₁₂ alkyl, carbazolyl, carbazolyl substituted by at least one C ₁ -C ₁₂ alkyl.
5. The boron-nitrogen compound according to any one of claims 1-4, wherein each occurrence of ^Rc is independently deuterium, fluorine, C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ alkoxy, C ₃ -C ₁₀ cycloalkyl, phenyl substituted by at least one C ₁ -C ₁₂ alkyl, phenyl-C ₁ -C ₁₂ alkyl, phenyl substituted by at least one C ₁ -C ₁₂ alkoxy , diphenylamino, diphenylamino substituted by at least one C ₁ -C ₁₂ alkyl, carbazolyl, carbazolyl substituted by at least one C ₁ -C ₁₂ alkyl;

   Preferably, each occurrence of R ^d is independently D (deuterium), fluorine, C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ alkoxy, C ₃ -C ₁₀ cycloalkyl, replaced by at least one C ₁ -C ₁₂ alkyl substituted phenyl, phenyl substituted by at least one C ₁ -C ₁₂ alkoxy, carbazolyl, carbazolyl substituted by at least one C ₁ -C ₁₂ alkyl.
6. The boron nitrogen compound according to any one of claims 1-5, wherein, said R ¹ and R ² are independently H, D (deuterium), fluorine, methyl, ethyl, n-propyl, isopropyl , n-butyl, tert-butyl, hexyl, octyl, decyl,

   

   Methoxy, Ethoxy, Butoxy, Hexyloxy,

   

   Cyclohexyl, adamantyl, phenyl, 4-methyl-phenyl, 4-ethyl-phenyl, 4-propyl-phenyl, 4-isopropylphenyl, 4-n-butylphenyl,

   

   

   

   

   Wherein the wavy line represents the connection site of the group;

   Preferably, said R ¹ and R ² are independently H, methyl,

   

   phenyl,

   

   

   

   Wherein the wavy line represents the connection site of the group;

   Preferably, said R ¹ and R ² are the same, selected from H, methyl,

   

   phenyl,

   

   

   any of the

   Wherein R ^g is H, methyl, isopropyl, tert-butyl or

   

   Preferably, ^R4 is H, C1-C8 alkyl, C6-C12 aryl, C5-C18 heteroaryl, C6-C12 aryl substituted by ^Rf or C5-C18 heteroaryl substituted by ^Rf ;

   R ^f is D (deuterium), fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, hexyl, octyl, decyl,

   

   Methoxy, Ethoxy, Butoxy, Hexyloxy,

   

   Cyclohexyl, adamantyl, phenyl, 4-methyl-phenyl, 4-ethyl-phenyl, 4-propyl-phenyl, 4-isopropylphenyl, 4-n-butylphenyl,

   

   

   

   

   Wherein the wavy line represents the connection site of the group;

   Preferably, said R ^f is H, methyl,

   

   phenyl,

   

   

   Wherein the wavy line represents the connection site of the group;

   Preferably, the R ⁴ is H, methyl,

   

   phenyl,

   

   

   R ^h is H, methyl, tert-butyl or

   

   Preferably, R ⁵ is H, C1～C8 alkyl, C6～C18 aryl or C5～C18 heteroaryl;

   Preferably, R ⁶ is H or methyl.
7. The boron-nitrogen compound according to any one of claims 1-6, wherein the boron-nitrogen compound is any one of the following compounds:

   

   

   

   

   

   

   

   

   

   

   

   

   

   
8. The preparation method of boron nitrogen compound according to any one of claims 1-7, it comprises the following steps:

   (1) In the presence of a catalyst, compound BN-Bpin reacts with compound B to obtain compound BN-DBTn, and the reaction formula is as follows:

   

   (2) Compound BN-DBTn ring-closing reaction occurs in the presence of ferric chloride, obtains the boron nitrogen compound shown in formula I, and reaction formula is as follows:

   
9. The preparation method of boron nitrogen compound according to claim 8, wherein the molar ratio of compound BN-Bpin to compound B in step (1) is 1:0.8～2;

   Preferably, the reaction described in step (1) is carried out in the presence of a weakly basic substance;

   Preferably, the weakly alkaline substance is potassium carbonate;

   Preferably, the catalyst described in step (1) is tetrakis (triphenylphosphine) palladium;

   Preferably, the amount of the catalyst in step (1) is 0.1% to 15% of the amount of the compound BN-Bpin;

   Preferably, the solvent of the reaction described in step (1) is tetrahydrofuran;

   Preferably, the reaction described in step (1) is carried out under reflux;

   Preferably, the reaction time of step (1) is 5-24 hours;

   Preferably, the amount of ferric chloride in step (2) is 3 to 50 times the amount of compound BN-Dpn;

   Preferably, the solvent of the ring closure reaction described in step (2) is dichloromethane;

   Preferably, the ring closure reaction described in step (2) is carried out at room temperature;

   Preferably, the time for the ring closure reaction in step (2) is 0.5-12 hours;

   Preferably, the reactions in step (1) and step (2) are carried out under nitrogen protection.
10. An organic electroluminescence composition, wherein, as a doping material, the boron nitrogen compound according to any one of claims 1-7 and a host material.
11. The organic electroluminescent composition according to claim 10, wherein the host material has electron transport capability and/or hole transport capability and its triplet excited state energy is higher than or equal to the triplet excited state energy of the dopant material s material.
12. The organic electroluminescent composition according to claim 10 or 11, wherein the host material is a carbazole derivative having a structure as shown in any one of formula (H-1) to formula (H-6) and/or carboline derivatives:

    

    Wherein X ₁ , Y ₁ and Z ₁ are CH or N, and at most one of X ₁ , Y ₁ and Z ₁ is N;

    Wherein R ^1H and R ^2H are independently any of the following groups:

    

    

    Wherein X ₁ , Y ₁ and Z ₁ are CH or N, and at most one of X ₁ , Y ₁ and Z ₁ is N;

    Where R ^aH and R ^bH are independently H, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, C ₆ -C ₂₀ aryl, C ₁ -C ₂₀ alkyl substituted C ₆ -C ₂₀ Aryl group or C ₆ -C ₂₀ aryl group substituted by C ₁ -C ₂₀ alkoxy group, * represents the connection site of the group;

    Preferably, the organic electroluminescent composition preferably contains 0.3-30.0wt% of the boron nitrogen compound as described in any one of claims 1-4 as a dopant material, and the remaining 99.7-70.0wt% of the composition It is a host material composed of 1-2 compounds with the structure of formula (H-1) to formula (H-6);

    Preferably, the host material contains two compounds having the structures of formula (H-1) to formula (H-6), and the weight ratio of the two compounds is 1:5 to 5:1;

    Preferably, the host material in the organic electroluminescent composition is one or two of compounds H1-1 to H1-427;

    Preferably, the organic electroluminescence composition contains 0.3-30.0wt% boron nitrogen compound with the structure shown in formula I as claimed in any one of claims 1-4, and the remaining 99.7-70.0wt% components is 1 or 2 compounds of compounds H1-1 to H1-427:

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    Preferably, the organic electroluminescent composition contains two compounds among compounds H1-1 to H1-427 as host materials, and the weight ratio of these two compounds is 1:5 to 5:1;

    Preferably, the dopant material in the organic electroluminescent composition is any one of the boron nitrogen compounds according to any one of claims 1-4; the host material is composed of formulas Trz1-A, Trz2-A , any one of the compounds shown in Trz3-A, Trz4-A, Trz5-A or Trz6-A and any one of the compounds with structures shown in formulas H-1 to H-6;

    

    

    One or two of R ^1a , R ^1b , R ^2a , R ^2b , R ^3a and R ^3b are independently R ^Tz , and the rest are the same or different and independently hydrogen, deuterium, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkoxy, C ₆ -C ₁₈ aryl, C ₁ -C ₈ alkyl substituted C ₆ -C ₁₈ aryl or C ₁ -C ₈ alkoxy substituted C ₆ -C ₁₈ Aryl; R ^Tz is any one of the substituting groups shown in the following formula:

    

    

    Wherein the asterisk represents the connection site of the group;

    Preferably, the compound shown in Trz1-A, Trz2-A, Trz3-A, Trz4-A, Trz5-A or Trz6-A in the host material is combined with H-1, H-2, H-3, H-4, H The weight ratio between the compounds shown in -5 or H-6 is 1:5 to 5:1;

    Preferably, the dopant material in the organic electroluminescent composition is any one of the above-mentioned boron nitrogen compounds with the structure shown in formula I; the host material is such as formula TRZ-1 to TRZ-76 Any one of the compounds shown and any one of the carbazole or carboline derivatives shown in formulas H1-1 to H1-427;

    

    

    

    

    Preferably, the weight ratio between the compound represented by the formulas TRZ-1 to TRZ-76 and the carbazole or carboline derivative in the host material is 1:5 to 5:1.
13. An organic electroluminescent material, wherein the organic electroluminescent material comprises the boron nitrogen compound according to any one of claims 1-7 or the organic electroluminescent compound according to any one of claims 10-12 Luminescent composition.
14. An organic electroluminescent device, wherein the organic electroluminescent device comprises an anode and a cathode and an organic thin film layer placed between the anode and the cathode, the organic thin film layer includes a light-emitting layer, an optional hole Injection layer, optional hole transport layer, optional electron transport layer, optional electron injection layer, wherein in the light emitting layer, electron injection layer, electron transport layer, hole transport layer, hole injection layer At least one layer comprises the boron nitrogen compound according to any one of claims 1-7 or the organic electroluminescent composition according to any one of claims 10-12;

    Preferably, the light emitting layer comprises the boron nitrogen compound according to any one of claims 1-7 or the organic electroluminescent composition according to any one of claims 10-12;

    Preferably, the organic electroluminescent device further comprises an optional hole blocking layer, an optional electron blocking layer and an optional capping layer.
15. The application of the organic electroluminescent device according to claim 14 in an organic electroluminescent display or an organic electroluminescent lighting source.

Images