B-n-containing organic electroluminescent material and application thereof in electroluminescent device

By introducing electron-withdrawing -N units into the BN structure, enhancing the multiple resonance effect and forming a large π conjugate plane, the problems of low efficiency and insufficient color purity of blue light materials in OLED devices are solved, achieving a high-efficiency, narrow half-wavelength light emission effect.

CN115806563BActive Publication Date: 2026-06-16GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS

Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
Filing Date
2022-06-08
Publication Date
2026-06-16

AI Technical Summary

Technical Problem

The blue light material in existing OLED devices is a fluorescent material with low internal quantum efficiency, which has not met the commercialization needs; TADF material has an excessively wide half-width spectrum, which is not conducive to high color purity display.

Method used

By introducing a BN structure and adding electron-withdrawing N units, the multiple resonance effect is enhanced, forming a large π conjugated plane, suppressing intramolecular vibrations, and developing highly efficient organic light-emitting materials with narrow half-wavelengths.

🎯Benefits of technology

It achieves high-efficiency blue light emission, meets commercial needs, and improves the color purity and luminous efficiency of the device.

✦ Generated by Eureka AI based on patent content.

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Abstract

The application provides a kind of B-N-containing organic electroluminescent material and its application in electroluminescent device.The B-N-containing organic electroluminescent material of the application has the structure as shown in general formula (I), (II) and (III).On the basis of B-N structure, the structure unit of electron-withdrawing-N is introduced into the material, which can effectively strengthen the multiple resonance effect of B-N structure, increase the Pi conjugated plane, and adjust the luminescent spectrum;and the aromatic group on the aromatic amine is fixed by the introduced electron-withdrawing group to form a large rigid Pi plane structure, which can effectively inhibit the vibration in the molecule, obtain a high-efficiency organic luminescent material with narrow half-wave width, and meet the commercialization demand.
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Description

Technical Field

[0001] This invention relates to the field of luminescent materials, specifically to a class of organic electroluminescent materials containing BN and their application in electroluminescent devices. Background Technology

[0002] Organic light emission diodes (OLEDs) have been widely used in the display and lighting industries, especially in mobile phone displays. The latest mobile phone products launched by manufacturers such as Apple, Sumsang, Huawei and Xiaomi all use OLED screens. This is mainly due to the excellent characteristics of OLEDs, such as self-emission, wide viewing angle, high contrast, fast response speed and the ability to fabricate flexible devices.

[0003] Currently commercially available OLED devices employ a multi-layered sandwich structure, including an anode, hole injection layer, hole transport layer, emissive layer, electron transport layer, electron injection layer, and cathode. Holes are generated at the anode and enter the emissive layer through the hole injection and transport layers, while electrons move from the cathode through the electron injection and transport layers to the emissive layer. Holes and electrons recombine in the emissive layer to generate excitons. These excitons transition from the excited state to the ground state, emitting visible light. To achieve color display, OLED devices utilize the additive color principle, meaning the emissive layer is further divided into blue, green, and red emissive layers, each using organic materials of different colors.

[0004] When applying OLED devices to displays, low driving voltage, high luminous efficiency, and long lifespan are required. Therefore, in the gradual improvement of display performance, organic materials have evolved from fluorescent materials to phosphorescent materials, and then to thermally activated delayed fluorescence materials (TADF). Currently, green and red light-emitting materials are phosphorescent materials, which can emit light using either singlet or triplet excitons, thus achieving an internal quantum efficiency of 100%. However, phosphorescent materials contain heavy metals, resulting in high prices and poor material stability. Blue light-emitting materials are fluorescent materials, which can only emit light using singlet excitons. Although the TTA (transformation of two triplet excitons into one singlet exciton) principle is used, its theoretical efficiency is only 40%, far below market demand. TADF materials utilize the small singlet-triplet energy level difference (ΔEST), allowing triplet excitons to cross between antisystems and transform into singlet excitons, thus achieving 100% internal quantum efficiency. However, TADF materials have strong charge transfer characteristics (CT) and a very wide half-width spectrum, which is not conducive to high color purity display. Summary of the Invention

[0005] To address the existing problems of the aforementioned organic materials, this invention provides a class of BN-based organic light-emitting materials and their applications in organic light-emitting devices. Based on the BN structure, this material introduces electron-withdrawing -N structural units, which effectively enhances the multiple resonance effect of the BN structure, expands the range of the multiple resonance effect, increases the π-conjugated plane, and modulates the emission spectrum. Furthermore, the aromatic groups on the aromatic amine are fixed by the introduced electron-withdrawing groups, forming a large, rigid π-planar structure, which effectively suppresses intramolecular vibrations, resulting in a high-efficiency organic light-emitting material with a narrow half-wavelength, meeting commercialization requirements.

[0006] This invention also provides a class of organic electroluminescent materials containing a BN structure, the general structural formula of which is shown in one of formulas (I), (II), and (III):

[0007]

[0008] in:

[0009] X1 to X4 are each independently selected from electron-withdrawing units.

[0010] Ar1 to Ar 10 Each of the following groups is independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 5-30 carbon atoms, or Ar1 and Ar2, Ar3 and Ar4, Ar4 and Ar5, Ar5 and Ar7 are independently linked into a ring by any one of the following bonds: single bond, -CC-, -C=C-, -C=N-, -C=P-, -C≡C-; the heteroatom of the heteroaryl group is one or more of N, S, O, P, B, and Si.

[0011] Ar1 to Ar 10 The substitutions are made by one or more of the following groups of substituents, each independently consisting of hydrogen, deuterium, cyano, nitro, halogen, hydroxyl, alkylthio with 1 to 4 carbon atoms, alkyl with 1 to 30 carbon atoms, cycloalkyl with 1 to 20 carbon atoms, aryloxy with 6 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, alkylamino with 1 to 30 carbon atoms, arylamino with 6 to 30 carbon atoms, arylalkylamino with 6 to 30 carbon atoms, heteroarylamino with 2 to 24 carbon atoms, alkylsilyl with 1 to 30 carbon atoms, arylsilyl with 6 to 30 carbon atoms, alkyl with 1 to 30 carbon atoms, alkenyl with 2 to 30 carbon atoms, alkynyl with 2 to 24 carbon atoms, aryl with 7 to 30 carbon atoms, aryl with 6 to 30 carbon atoms, heteroaryl with 5 to 60 carbon atoms, or heteroarylalkyl with 6 to 30 carbon atoms.

[0012] The aryl group is selected from one or more of phenyl, naphthyl, anthracene, binatyl, phenanthrene, dihydrophenanthrene, peryl, perylene, tetraphenyl, pentaphenyl, benzo[a]perylene, benzocyclopentadienyl, spirofluorenyl, and fluorenyl.

[0013] Preferably, the aryl group is selected from one or more of phenyl, naphthyl, anthracene, phenanthrene, dihydrophenanthrene, tetraphenyl, pentaphenyl, benzo[a]perylene, benzocyclopentadienyl, spirofluorenyl, and fluorenyl.

[0014] The heteroaryl group is selected from pyrrole, imidazolyl, thiophene, furanyl, 1,2-thiazolyl, 1,3-thiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, thiazolyl, selenidiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, pyridyl, pyrazinyl, pyrimidinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, indole, isoindole, benzimidazole, naphzimidazole, phenanthrene. Imidazole, benzotriazole, purine, benzoxazole, naphthoxazole, phenanthreneoxazole, benzothiadiazole, benzoselenodiazole, benzotriazole, quinolinyl, isoquinolinyl, benzopyrazinyl, benzothiophene, benzofuranyl, benzopyrroleyl, carbazole, acridineyl, dibenzothiophene, dibenzofuranyl, silanyl, dibenzothiophene-5,5-dioxy, naphthothiadiazole, naphthoselenodiazole, and 10,15-dihydro-5H-diindolo[3,2] -a:3',2'-c]carbazole group or one or more of the following: The heteroaryl group is most preferably selected from pyrrole, imidazolyl, thiophene, furanyl, 1,2-thiazolyl, 1,3-thiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, thiazolyl, selenidiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, pyridyl, pyrazinyl, pyrimidinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2, One or more of the following: 3-triazinyl, indole, isoindole, benzimidazole, naphzimidazole, phenanthreneimidazole, benzotriazole, purine, benzoxazole, naphzimidazole, phenanthrenexaazole, benzothiadiazolyl, benzotriazolyl, quinolinyl, isoquinolinyl, benzopyrazinyl, benzothiophenyl, benzofuranyl, benzopyrroleyl, carbazoyl, acridineyl, dibenzothiophenyl, dibenzofuranyl, dibenzothiophene-5,5-dioxy, naphzimidazolyl, naphziselenodiazolyl, and 10,15-dihydro-5H-diindolo[3,2-a:3',2'-c]carbazoyl.

[0015] Preferably, its general structural formula is shown in one of formulas (a)-(i).

[0016]

[0017] In structural formulas (a)-(i), the Ar1-Ar 10 The definitions are the same as those in structural formulas (I)-(III).

[0018] More preferably: Ar1, Ar2, Ar4, Ar6, Ar8, and Ar in structural formulas (a)-(i) 10 Ar3 and Ar5 are independently selected from one of Ar-1 to Ar-28; Ar7 is selected from one of Ar-66 to Ar-93; and Ar9 is selected from one of Ar-94 to Ar-99.

[0019]

[0020]

[0021]

[0022] Wherein, P1 represents the site connected to the boron atom, and P2, P3, P4, and P5 represent the sites connected to X1, X2, X3, X4, and the nitrogen atom, respectively. The dashed lines represent the corresponding bonds.

[0023] R1 is independently selected from one of the following: hydrogen atom, protium atom, deuterium atom, tritium atom, fluorine atom, cyano group, phosphate or its salt, straight-chain or branched C1-20 alkyl group, straight-chain or branched C1-20 alkyl-substituted silyl group, C6-30 substituted or unsubstituted aryl group, C5-30 substituted or unsubstituted heteroaryl group, or R1 is connected to each other by a single bond, -CC-, -C=C-, -C=N-, -C=P-, -C≡C-. The aryl group is formed into a ring by any one of the following bonds; the heteroatom in the heteroaryl group is selected from one or more of N, O or S, and the substituted aryl or heteroaryl group is replaced by a halogen element or a C1-C4 alkyl group.

[0024] Preferably, R1 is independently selected from one of hydrogen atom, protium atom, deuterium atom, tritium atom, fluorine atom, cyano group, straight-chain or branched C1-8 alkyl group, C6-10 substituted or unsubstituted aryl group, C5-10 substituted or unsubstituted heteroaryl group, or R1 is linked to each other by a single bond or -CC- bond to form a ring; the heteroatom in the heteroaryl group is selected from one or more of N, O or S, and the aryl or heteroaryl group is substituted by C1-C4 alkyl group.

[0025] More preferably, R1 is independently selected from hydrogen atoms, straight-chain or branched C1-4 alkyl groups, phenyl groups, or R1s are linked together to form a ring by any one of single bonds or -CC- bonds.

[0026] Its general structural formula is shown in formula (a) or (d), where Ar1 and Ar2 are as shown in one of Ar-1 to Ar-16 and Ar-19 to Ar-26, Ar4 is as shown in one of Ar-1, Ar-4, Ar-6, Ar-8, Ar-10, Ar-11, Ar-16, and Ar-25, and Ar3 and Ar5 are as shown in one of Ar-29, Ar-32, Ar-34, Ar-36, Ar-37, Ar-38, Ar-54, Ar-59, and Ar-64.

[0027] Its structure is shown in the following formula, but is not limited to the listed structural formulas:

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035] The second invention is to provide an organic electroluminescent device, the organic electroluminescent device comprising at least one functional layer of an organic electroluminescent material containing a BN fused ring;

[0036] Preferably, BN fused-ring organic electroluminescent material is used as the light-emitting layer material;

[0037] More preferably, BN fused-ring organic electroluminescent material is used as a dopant or sensitizer material for the light-emitting layer;

[0038] This invention provides a class of organic light-emitting materials based on boron and nitrogen (BN) and their applications in organic light-emitting devices. These materials, based on the BN structure, introduce electron-withdrawing -N structural units, which effectively enhances the multiple resonance effect of the BN structure, expands the range of the multiple resonance effect, increases the π-conjugated plane, and modulates the emission spectrum. Furthermore, the aromatic groups on the aromatic amine are fixed by the introduced electron-withdrawing groups, forming a large, rigid π-planar structure, which effectively suppresses intramolecular vibrations, resulting in highly efficient organic light-emitting materials with narrow half-wavelengths, meeting commercialization requirements. Attached Figure Description

[0039] Figure 1 This is a schematic diagram of the organic electroluminescent bottom-emitting device of the present invention. Detailed Implementation

[0040] This invention does not require specific methods for synthesizing the materials. To describe the invention in more detail, the following examples are provided, but the invention is not limited thereto. Unless otherwise specified, all raw materials used in the following synthesis are commercially available products.

[0041] Example 1:

[0042] Synthesis of compound structure 1:

[0043]

[0044] Synthesis of compound 1c:

[0045] A 100 mL three-necked flask was filled with (1b) (845 mg, 2.56 mmol), (1a) (1.0 g, 5.12 mmol), CuI (346 mg, 1.82 mmol), potassium carbonate (2.12 g, 15.4 mmol), and DMF (40 mL). The mixture was stirred at 180 °C for 22 h under nitrogen protection. After the reaction was complete, 100 mL of water was added with stirring to precipitate the product. After filtration, the product was dissolved in 10 mL of DCM and precipitated again with 100 mL of n-hexane. The precipitate was then obtained by filtration, yielding a yellow crude product. Silica gel column chromatography was performed to separate the product into 0.6 g of a yellow solid powder, with a yield of 50.4%. The 1H NMR data are as follows: 1 H NMR (400MHz, CDCl3) δ8.21(d,4H),8.15(d,1H),7.70(t,4H), 7.52(d,6H),7.23(t,5H).

[0046] Synthesis of Compound 1:

[0047] In a three-necked flask, 1c (300 mg, 0.6 mmol) and o-CB (30 ml) were added. The nitrogen atmosphere was purged three times. BI3 (0.99 g, 2.4 mmol) was weighed and rapidly added to the flask in a fume hood. After stirring for 0.5 h, the mixture was heated to 200 °C and reacted for 48 h. After the reaction was complete, the mixture was cooled and filtered. The filter cake was ultrasonically treated with DCM and n-hexane, and filtered again to obtain 30 mg of a yellow powder, with a yield of 11%. The 1H NMR data are as follows: 1 HNMR (400MHz, CDCl3) δ8.06 (dd, J=7.7, 1.6Hz, 2H), 8.01 (dd, J=7.3, 1.1Hz, 2H),7.77(dd,J=7.5,1.1Hz,2H),7.56(ddd,J=8.1,7.2,1.6Hz,2H),7.38(ddd,J=8.6,7.2,1.5Hz,2H),7.34–7.25(m,5H),6.91–6.85(m,2H).

[0048] Example 2:

[0049] Synthesis of compound structure 2:

[0050]

[0051] The synthesis was the same as that of compound 1, except that the starting material 1a was changed to 2a, and compound 2 was a yellow powder with a yield of 8%. 1 H NMR (400MHz, CDCl3) δ8.00(d,J=2.0Hz,2H),7.89(d,J=2.2Hz,2H),7.63(d,J=2.2Hz ,2H),7.41(dd,J=6.9,2.1Hz,2H),7.34–7.27(m,3H),6.91–6.85(m,2H),1.34(d,J= 4.8Hz,36H).

[0052] Example 3:

[0053] Synthesis of compound structure 8:

[0054]

[0055] Synthesis of compound 8c:

[0056] Take a 100 mL three-necked flask and add (8b) (0.85 g, 3.0 mmol), (1a) (0.6 mg, 3.1 mmol), CuI (0.23 g, 1.2 mmol), potassium carbonate (1.24 g, 9.0 mmol), and DMF (50 mL). Under nitrogen protection, stir the mixture at 150 °C for 12 h. After the reaction is complete, add 100 mL of water with stirring to precipitate the product. Filter and dry the product. Dissolve the filter cake in dichloromethane and separate it by silica gel column chromatography to obtain 0.77 g of a yellow solid, with a yield of 74%. The 1H NMR data are as follows: 1 H NMR (400MHz, CDCl3) δ8.05(dd,J=7.7,1.6Hz,2H),7.52(ddd,J=8.0,7.3,1.8Hz,2H),7.37(dd,J=7.2,1.4 Hz,1H),7.35–7.24(m,6H),7.11(ddd,J=7.0,2.3,1.4Hz,1H).

[0057] Synthesis of compound 8e:

[0058] A 100 mL three-necked flask was filled with (8c) (0.7 g, 2.0 mmol), (8d) (0.61 mg, 2.21 mmol), CuI (0.23 g, 1.2 mmol), potassium carbonate (1.24 g, 9.0 mmol), and DMF (50 mL). The mixture was stirred at 180 °C for 12 h under nitrogen protection. After the reaction was complete, 100 mL of water was added with stirring to precipitate the product. The precipitate was filtered, dried, and dissolved in dichloromethane. The product was then separated by silica gel column chromatography to obtain 0.91 g of a yellow solid, with a yield of 83%. The 1H NMR data are as follows: 1 ¹H NMR (400MHz, CDCl₃) δ 8.07 (ddd, J = 12.9, 7.7, 1.7Hz, 3H), 7.68–7.59 (m, 2H), 7.57–7.48 (m, 3H), 7.42 (qd, J = 4.1, 3.6, 1.7Hz, 3H), 7.39–7.25 (m, 8H), 7.02 (dt, J = 7.3, 1.4Hz, 2H), 6.34 (t, J = 1.9Hz, 1H). Synthesis of compound 8:

[0059] The synthesis was the same as that of compound 1, with a yield of 12%. The proton NMR data are as follows: 1 H NMR (400MHz, CDCl3) δ8.10 (dd, J=7.7, 1.9Hz, 1H), 8.06 (dd, J=7.7, 1.5Hz, 1H), 8.01 (dd, J=7.3, 1.1Hz, 1H), 7.66 (dd, J=7.5, 1.1Hz,1H),7.64–7.53(m,4H),7.44–7.38(m,5H),7.35–7.23(m,4H),6.88(ddd,J=7.1,5.9, 1.1Hz,2H).

[0060] Example 4:

[0061] Synthesis of compound structure 121:

[0062]

[0063] Synthesis of compound 121c:

[0064] The synthesis was similar to that of compound 1c, with the difference in reactants being 1a changed to 121a and 1b changed to 8b. The yield of 121c was 68%. The proton NMR data are as follows: 1H NMR (400MHz, CDCl3) δ7.40–7.34(m,7H),7.32(dd,J=6.8,1.5Hz,5H),7.29(dd,J=7. 2,1.4Hz,1H),7.23–7.14(m,4H),7.01(dd,J=7.3,2.0Hz,2H),6.34(t,J=2.1Hz,1H).

[0065] Synthesis of compound 121d:

[0066] 0.95 g (2 mmol) of 121°C and 20 mL of acetic acid were added to a three-necked flask and heated to 100°C. 5 mL of H₂O₂ was slowly added from above the reflux condenser, and the reaction was allowed to proceed for 2 h. After cooling to room temperature, the mixture was filtered directly. The filter cake was pulped using DCM and filtered again to obtain 0.87 g of a white powder, with a yield of 81%. The 1H NMR data are as follows: 1 H NMR (400MHz, DMSO-d) 6 )δ8.38–7.87(m,8H), 7.64(s,4H),7.41(s,4H),6.83(s,4H).

[0067] Synthesis of compound 121:

[0068] The synthesis was the same as that of compound 1, with a yield of 7%. The proton NMR data are as follows: 1 H NMR (400MHz, DMSO-d) 6 )δ7.92(ddd,J=8.5,3.8,1.3Hz,4H),7.68(dd,J=7.3,1.1Hz,2H),7.57–7.48(m,4H),7.44(ddd,J= 7.7,7.0,1.5Hz,2H),7.34–7.23(m,3H),6.91–6.85(m,2H).

[0069] Example 5:

[0070] Synthesis of compound structure 124:

[0071]

[0072] Synthesis of compound 124a:

[0073] The synthesis was similar to that of compound 121c, with the only difference being the feed ratio of 121a, which changed from 2 eq to 1.2 eq. The yield of 124a was 87%. The proton NMR data are as follows: 1¹H NMR (400MHz, CDCl₃) δ 7.39–7.35 (m, 3H), 7.32 (m, 5H), 7.28 (m, 1H), 7.21–7.15 (m, 2H), 7.10 (m, 1H). Synthesis of compound 124b:

[0074] The synthesis was the same as that of compound 124a, except that 121a was replaced with 124a and 121b with 124b, with a yield of 73%. The proton NMR data are as follows: 1 H NMR(400MHz, CDCl3) δ7.99(d,J=1.8Hz,1H),7.86(m,2H),7.79(d,J=1.9Hz,1 H),7.55–7.48(m,2H),7.39–7.27(m,12H),7.22–7.14(m,3H),6.34(t,J=2.1 Hz,1H).

[0075] Synthesis of compound 124:

[0076] The synthesis was the same as that of compound 121, except that 121c was changed to 124c, with a yield of 10%. The proton NMR data are as follows: 1 H NMR (400MHz, DMSO-d) 6 )δ8.36(d,J=1.8Hz,1H),7.98(dd,J=7.3,1.1Hz,1H),7.92(m,3H),7.83(dt,J=7.3,1.6Hz,1H),7.69(dd,J=7.3,1. 1Hz,1H),7.58–7.48(m,4H),7.48–7.41(m,4H),7.36(td,J=7.2,1.3Hz,1H),7.33–7.21(m,2H),6.91–6.84(m,2H).

[0077] Example 6:

[0078] Synthesis of compound structure 134:

[0079]

[0080] The synthesis was the same as that of compound 124, except that 124b was replaced by 134a, and the yield of 134 was 7%. The proton NMR data are as follows: 1 H NMR (400MHz, DMSO-d) 6)δ8.03–7.88(m,3H),7.83(dd,J=7.3,1.1Hz,1H),7.79–7.71 (m,2H),7.63–7.50(m,5H),7.50–7.40(m,4H),7.36–7.23(m,2H),6.88(m,2H).

[0081] Those skilled in the art should understand that the above preparation method is merely an exemplary example, and they can obtain other compound structures of the present invention by improving it.

[0082] Example 7:

[0083] Organic electroluminescent bottom-emitting devices were fabricated using the BN organic electroluminescent material of the present invention. The device structure is shown in [see figure]. Figure 1 First, the transparent conductive ITO glass substrate 10 (with an anode 20 on it) is sequentially washed with deionized water, ethanol, acetone, and then deionized water, dried at 80°C, and then treated with oxygen plasma for 30 minutes. Then, it is deposited in a vacuum <4*10⁻⁶ vacuum vapor deposition machine. -4 A 10 nm thick HATCN layer was deposited as a hole injection layer 30 under the conditions of Pa; a 40 nm thick hole transport layer 40 was formed by depositing compound HTL; a 10 nm thick EBL (electron blocking layer) 50 was deposited on the hole transport layer; then a 40 nm thick EML (host material (host1:host2 = 1:1):guest material = 94:6%, emitting layer) 60 was deposited, the emitting layer being composed of BN organic electroluminescent material (structure 1, 6%) and host material doped together; a 40 nm thick ETL (electron transport layer) 70 was deposited on the emitting layer, the electron transport layer being composed of ETL1 and LiQ materials. A 1 nm thick ytterbium metal was deposited as an electron injection layer 80 and a 100 nm thick Ag metal was deposited as the device cathode 90.

[0084]

[0085] Examples 8-12 and Comparative Example 1:

[0086] The organic electroluminescent devices of Examples 8-12 and Comparative Example 1 were fabricated in the same way as those of Example 7, except that the guest materials in the light-emitting layer were respectively Structure 2, Structure 8, Structure 121, Structure 122, Structure 134 and Comparative Example 1 of the present invention.

[0087] Example 13:

[0088] The fabrication process of the organic electroluminescent device in Example 13 is the same as that in Example 7, except that its light-emitting layer material is composed of host 3 and comparative example 2 (host 3: comparative example 2 = 97%: 3%), and the thickness is 20 nm.

[0089] The chemical structures of the materials in Comparative Example 1 and Comparative Example 2 are as follows:

[0090]

[0091] The electrical and optical properties of the electroluminescent devices of Examples 7-12 and Comparative Examples 1 and 2 were measured at 0.4 mA, as shown in Table 1.

[0092] Table 1

[0093]

[0094]

[0095] As can be seen from the data in Table 1, under the same conditions, the BN organic electroluminescent material of the present invention, when applied to organic electroluminescent devices, has a narrow half-width, that is, it has higher color purity in top-emitting devices (compared to Comparative Example 1), thus achieving a better display effect. Compared with Comparative Example 2, the emission wavelength of the BN organic electroluminescent material of the present invention is significantly red-shifted and located in the green light region (>500nm), and the emission color can be adjusted, unlike conventional BN organic electroluminescent materials (Comparative Example 2, emission wavelength: 459nm).

Claims

1. A class of organic electroluminescent materials containing a BN structure, the structure of which is shown in one of the general formulas: , in: Ar1 is selected from substituted or unsubstituted phenyl or naphthyl groups; Ar2 to Ar5 are each independently selected from substituted or unsubstituted phenyl groups; The substitutions in Ar1 to Ar5 are each replaced by one or more of a group of substituents consisting of deuterium, cyano, or alkyl groups having 1 to 30 carbon atoms.

2. The organic electroluminescent material according to claim 1, wherein Ar1 is selected from Ar-1 and Ar-4, Ar2 and Ar4 are selected from Ar-1, and Ar3 and Ar5 are independently selected from Ar-29; R1 is independently selected from hydrogen atoms, deuterium atoms, cyano groups, or straight-chain or branched C1-20 alkyl groups; in, In Ar4, P1 represents the site bonded to a boron atom, and P2 and P3 represent the sites bonded to nitrogen atoms, respectively. The dashed lines represent the corresponding bonds. In Ar1 and Ar2, P2 represents the site bonded to a boron atom, and P1 and P3 represent the sites bonded to a nitrogen atom, CO, or SO2, respectively. In Ar3 and Ar5, P2 and P3 represent the sites bonded to CO or SO2 and nitrogen atoms, respectively. The dashed lines represent the corresponding bonds. 。 3. In the organic electroluminescent material according to claim 2, R1 is independently selected from hydrogen atoms, deuterium atoms, cyano groups, or straight-chain or branched C1-8 alkyl groups.

4. The organic electroluminescent material according to claim 3, wherein R1 is independently selected from hydrogen atom, deuterium atom, cyano group or straight-chain or branched C1-4 alkyl group.

5. The organic electroluminescent material according to claim 1, wherein the structure is shown in one of the following formulas: 。 6. A class of organic electroluminescent materials containing a BN structure, the structure of which is shown in one of the general formulas: , in: Ar1 is independently selected from substituted thiophene or substituted furanyl, and Ar2 to Ar5 are each independently selected from substituted or unsubstituted phenyl groups; The substitution in Ar1 is achieved by substituted aryl groups having 6 to 10 carbon atoms; The substitutions in Ar2 to Ar5 are each replaced by one or more of a group of substituents consisting of deuterium, cyano, alkyl with 1 to 30 carbon atoms, or cycloalkyl with 1 to 20 carbon atoms.

7. The organic electroluminescent material according to claim 6, wherein Ar1 is selected from Ar-13 and Ar-14, Ar2 and Ar4 are independently selected from Ar-1, and Ar3 and Ar5 are independently selected from Ar-29. in, In Ar4, P1 represents the site bonded to a boron atom, and P2 and P3 represent the sites bonded to a nitrogen atom, respectively. The dashed lines represent the corresponding bonds. In Ar1 and Ar2, P2 represents the site bonded to a boron atom, and P1 and P3 represent the sites bonded to a nitrogen atom, CO, or SO2, respectively. In Ar3 and Ar5, P2 and P3 represent the sites bonded to CO or SO2 and a nitrogen atom, respectively. The dashed lines represent the corresponding bonds. In Ar1, R1 is selected from C6-10 aryl groups; in Ar2-Ar5, R1 is independently selected from one of hydrogen atoms, deuterium atoms, cyano groups, straight-chain or branched C1-20 alkyl groups.

8. The organic electroluminescent material according to claim 7, wherein R1 in Ar1 is selected from phenyl, and R1 in Ar2-Ar5 is independently selected from one of hydrogen atom, deuterium atom, cyano group, straight-chain or branched C1-4 alkyl group.

9. The organic electroluminescent material according to claim 6, wherein the structure is shown in one of the following formulas: 。 10. An electroluminescent device, characterized in that: It includes a functional layer, wherein the material of the functional layer contains the organic electroluminescent material according to any one of claims 1-9.

11. An electroluminescent device, characterized in that: It includes a light-emitting layer, wherein the doping material or sensitizer material of the light-emitting layer contains the electroluminescent material according to any one of claims 1-9.

12. A lighting element, characterized in that: Includes the electroluminescent device according to any one of claims 10-11.

13. A display element, characterized in that: Includes the electroluminescent device according to any one of claims 10-11.