Luminescent material, application thereof, and organic electroluminescent device containing same

Abstract

The present invention relates to the field of organic electroluminescence technology, and in particular to an organic compound and its application, as well as an organic electroluminescent device containing the compound. The compound of the present invention has a structure as shown in the following formula (1), wherein X1 and X2 are independently represented by O, S or N(R1), and at least one of X1 and X2 is N(R1); A represents a substituted or unsubstituted C6~C 60 Carbocyclic group, substituted or unsubstituted C3~C 60 A heterocyclic group. In the general compound structure, an aromatic ring or heteroaromatic ring with a specific number of carbon atoms acts as a large steric protecting group to inhibit interactions between planar boron-containing / nitride-containing molecules, thereby achieving the excellent properties of the present invention's compounds, including a narrow half-width and high fluorescence quantum yield, while also exhibiting a high glass transition temperature, molecular thermal stability, and resistance to aggregation quenching. The compounds of the present invention can be used as dopants in the light-emitting layer of organic electroluminescent devices, improving the device's luminescent color purity and lifetime.

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescence, and in particular to an organic compound and application thereof, and an organic electroluminescent device containing the compound. Background Art

[0002] Organic light-emitting diodes (OLEDs) are a type of device with a sandwich-like structure, consisting of positive and negative electrode layers sandwiched between layers of organic functional materials. OLEDs, due to their advantages such as high brightness, fast response, wide viewing angle, simple processing, and flexibility, have attracted considerable attention in the fields of new display and lighting technologies. Currently, this technology is widely used in display panels for new lighting fixtures, smartphones, and tablets, and is poised to expand into larger display products such as televisions. It is a rapidly developing and technologically demanding new display technology.

[0003] As OLEDs continue to advance in the fields of lighting and display, research on their core materials has become increasingly focused. This is because an efficient and long-lasting OLED device is typically the result of an optimized combination of device structure and various organic materials. To produce OLED light-emitting devices with lower driving voltages, better luminous efficiency, and longer device lifespans, and to continuously improve the performance of OLED devices, not only innovations in OLED device structure and manufacturing processes are required, but also continuous research and innovation in the optoelectronic functional materials used in OLED devices to produce functional materials with higher performance. For this reason, the OLED materials community has been committed to developing new organic electroluminescent materials to achieve low device startup voltages, high luminous efficiency, and improved device lifespans.

[0004] In the selection of OLED materials, singlet-state fluorescent materials have good lifespan and low price, but low efficiency; triplet-state phosphorescent materials have high efficiency, but are expensive, and the lifespan problem of blue light materials has not been solved. Adachi of Kyushu University in Japan proposed a new type of organic light-emitting material, namely thermally activated delayed fluorescence (TADF) material. The singlet-triplet energy gap (ΔE ST ) is very small (<0.3 eV), and triplet excitons can be converted into singlet excitons through reverse intersystem crossing (RISC) to emit light, so the internal quantum efficiency of the device can reach 223%.

[0005] Multi-resonance (MR) materials have the advantages of high color purity and high luminous efficiency, attracting widespread attention from the scientific research and industry. However, due to the relatively planar structural characteristics of MR dyes, they are very prone to molecular aggregation, resulting in a dramatic broadening of the spectrum and a sharp decrease in luminous efficiency. Typically, the doping concentration corresponding to the optimal device performance of this type of material is often less than 1wt%. Moreover, due to the small Stokes shift of narrow-spectrum dyes, the energy between the host and the guest is difficult to be fully distributed under low concentration conditions. Further increasing the concentration will lead to a decrease in efficiency and color purity. Therefore, the evaporation window is very narrow and the process requirements are very complex. Summary of the Invention

[0006] In order to solve the above technical problems, the present invention provides an organic compound, the specific general formula of the compound of the present invention is shown in the following formula (1) or formula (2):

[0007]

[0008] In formula (1), X1 and X2 are each independently O, S or N(R1) and at least one of X1 and X2 is N(R1);

[0009] In formula (1), A represents a substituted or unsubstituted C6-C 60 Carbocyclic group, substituted or unsubstituted C3~C 60 A is a substituted carbocyclic group or a substituted heterocyclic group, which is selected from deuterium, tritium, cyano, halogen, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, silicon, C6~C 30 Aromatic amino group, C6~C 30 Aryl, C2~C 30 substituted by one or a combination of at least two heteroaryl groups, wherein the substituents are independently connected to the connected aromatic ring or heteroaromatic ring to form a ring or are not connected to form a ring;

[0010] In formula (1), Z1-Z 10 Each of the R groups is independently represented by N or CR, each occurrence of R may be the same or different, and two adjacent R groups may be bonded to each other to form a ring;

[0011] R1 can be connected to the adjacent R through a single bond;

[0012] R1 represents a substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0013] R represents hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 30 Aryloxy, substituted or unsubstituted C6~C 30 Arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0014] The substitution in the above R1 and R is substituted or unsubstituted, which means being selected from deuterium, tritium, cyano, halogen, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, silicon, C6~C 30 Aromatic amino, C6~C 30 Aryl, C2~C 30 The substituents are substituted by one or a combination of at least two heteroaryl groups, and the substituents are independently connected to the connected aromatic ring or heteroaromatic ring to form a ring or are not connected to form a ring.

[0015] Preferably, the general compound of the present invention has a structure as shown in any one of the following formulas (1-1), (1-2) or (1-3):

[0016]

[0017] The Z1-Z 10 Each is independently represented by CR, and the definitions of A, R, and R1 are the same as those above;

[0018] More preferably, R1 is connected to the adjacent R via a single bond.

[0019] Furthermore, in the above general formula, A represents the following substituted structural groups:

[0020]

[0021] The asterisk in the above structure indicates a connection site, which can be connected to the parent core or connected to a substituent group; the expression of a ring structure crossed by "—" indicates that the connection site is any position on the ring structure that can form a bond; the dotted line in the above structure indicates connection or non-connection;

[0022] The substitution in the structural group where A is substituted refers to a group selected from deuterium, tritium, cyano, halogen, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aromatic amino, C6~C30 Aryl, C2~C 30 The substituents are substituted by one or a combination of at least two heteroaryl groups, and the substituents are independently connected to the connected aromatic ring or heteroaromatic ring to form a ring or are not connected to form a ring.

[0023] Furthermore, or in the above general formula, A is represented by any one of the following structural formulas:

[0024]

[0025] wherein R3 and R4 are independently hydrogen, deuterium, tritium, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C3~C 30 Cycloalkyl, silicon, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted C6~C 60 Aryloxy, substituted or unsubstituted C6~C 60 Arylamine, substituted or unsubstituted C6~C 60 Aryl, substituted or unsubstituted C2~C 60 Any of heteroaryl groups;

[0026] Z is independently represented by N or CR5, R5 is the same or different each time, and two adjacent R5 can be bonded to each other to form a ring; R5 is represented by hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1~C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C6~C 30 Aryloxy, substituted or unsubstituted C6~C 30 Arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0027] The substitution in the above R3, R4, and R5 is substituted or unsubstituted, and refers to being selected from deuterium, tritium, cyano, halogen, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, silicon, C6~C 30 Aromatic amino, C6~C 30 Aryl, C2~C 30 The substituents are substituted by one or a combination of at least two heteroaryl groups, and the substituents are independently connected to the connected aromatic ring or heteroaromatic ring to form a ring or are not connected to form a ring.

[0028] Furthermore, in the above general formula, R3 and R4 are independently represented by substituted or unsubstituted C1~C 30Alkyl, substituted or unsubstituted C3-C 30 Cycloalkyl, substituted or unsubstituted C6~C 60 Aryl, substituted or unsubstituted C2~C 60 Any of heteroaryl groups;

[0029] More preferably, at least one of R3 and R4 is selected from one of the following bulky steric groups: terphenyl, triphenyl, quaternary, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, trimeric indenyl, isotrimeric indenyl, spirotrimeric indenyl, spiroisotrimeric indenyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, isoindolyl, carbazolyl, indenocarbazolyl, isoquinolinyl, azoxybenzotriazole, benzoxazolyl, benzophenanthridine, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, benzimidazolyl, naphthioimidazolyl, phenanthroimidazolyl, pyridinoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthioxazolyl, anthrazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1, 6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, phenazinyl, phenothiazinyl, azacarbazolyl, benzocarbolyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl , 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, diphenylamino, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, silicon, or at least one of R3 and R4 is selected from a combination of two or more of the above-mentioned bulky steric groups.

[0030] Furthermore, in the above general formula, R represents hydrogen, deuterium, tritium, fluorine, cyano, methyl, deuterated methyl, tritiated methyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, deuterated cyclopentyl, tritiated cyclopentyl, cyclohexyl, cyclopentyl, adamantyl, phenyl, deuterated phenyl, tritiated phenyl, biphenyl , deuterated biphenyl, tritiated biphenyl, deuterated terphenyl, tritiated terphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyridyl, quinolyl, furyl, thienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, methyl substituted phenyl, ethyl substituted phenyl, isopropyl substituted One of phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, tritiated methyl-substituted phenyl, tritiated ethyl-substituted phenyl, tritiated isopropyl-substituted phenyl, tritiated tert-butyl-substituted phenyl, tritiated methyl-substituted biphenyl, tritiated ethyl-substituted biphenyl, tritiated isopropyl-substituted biphenyl, tritiated tert-butyl-substituted biphenyl, diphenylamino, diphenylamino, and triphenylamino;

[0031] Furthermore, in the above general formula, R1 is methyl, deuterated methyl, tritiated methyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, deuterated cyclopentyl, tritiated cyclopentyl, cyclopentyl, adamantyl, phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl , tritiated diphenyl, deuterated terphenyl, tritiated terphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyridyl, quinolyl, furyl, thienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, methyl substituted phenyl, ethyl substituted phenyl, isopropyl substituted The present invention further comprises one of deuterated phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, tritiated methyl-substituted phenyl, tritiated ethyl-substituted biphenyl, tritiated isopropyl-substituted phenyl, tritiated tert-butyl-substituted phenyl, tritiated methyl-substituted biphenyl, tritiated ethyl-substituted biphenyl, tritiated isopropyl-substituted biphenyl, and tritiated tert-butyl-substituted biphenyl.

[0032] More preferably, in the above general formula of the present invention, the Z9, Z 10 are CR, and R is hydrogen, and Z1-Z8 are CR, and the definition of R is the same as above; or, Z2 and Z7 are CR, and R is tert-butyl, and Z1, Z3-Z6, Z8-Z 10 are CR, and the R is hydrogen.

[0033] The compounds of this general formula of the present invention are preferably selected from the following specific structural compounds, but are not limited to the following specific compounds:

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059] A second object of the present invention is to provide a use of the compound described in the first object, wherein the compound is used in an organic electroluminescent device. Preferably, the compound is used as a light-emitting layer material in the organic electroluminescent device, preferably a light-emitting dye.

[0060] The third object of the present invention is to provide an organic electroluminescent device. Specifically, an embodiment of the present invention provides an organic electroluminescent device, comprising a substrate, and an anode layer, a plurality of light-emitting functional layers, and a cathode layer sequentially formed on the substrate; the light-emitting functional layer comprises a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is between the hole transport layer and the electron transport layer; wherein, preferably, the light-emitting layer contains the compound of the general formula of the present invention shown in any of the above general formulas, or the light-emitting layer contains at least any one of the above-mentioned specific compounds S-1 to S-294.

[0061] The compounds of the present invention are preferably used as light-emitting layer materials in organic electroluminescent devices. It is speculated that the reasons are as follows:

[0062] The compound of the present invention introduces a carbocyclic group or heterocyclic group represented by A coated with a large steric group into the molecular structure, which can effectively suppress the interaction between the molecules of the planar multiple resonance compound, thereby effectively suppressing the broadening of the spectrum and the reduction of the luminous efficiency of the compound at high concentrations. The design scheme of the compound molecular configuration of the present invention has at least two advantages compared to the prior art of directly introducing a large steric group on the parent nucleus skeleton. On the one hand, the feasibility of the chemical synthesis of the new compound is higher, and it is easy to modify a variety of different functions; on the other hand, in the general formula of the present invention, X1 and X2 are designed to be independently represented by O, S or N(R1), and at least one of X1 and X2 is N(R1). In this way, the ultra-narrow luminescence characteristics of the boron nitrogen system can be utilized as much as possible to ensure the narrow half-peak width of the entire molecular system. By further introducing a large steric group at the A position in the compound general formula, only the multiple resonance parent nucleus is protected without affecting the luminous color and half-peak width. The molecular configuration design of the compound disclosed herein is a versatile and effective strategy for addressing concentration aggregation and quenching. Specifically, in sensitized systems, it can significantly suppress Dexter energy transfer between host and guest materials in the light-emitting layer of organic electroluminescent devices, thereby significantly improving device efficiency, stability, and the evaporation window width. Furthermore, because the interactions between the host and guest molecules in the light-emitting layer are suppressed, extremely narrow undoped electroluminescence (FWHM <30nm) can be achieved.

[0063]

[0064] The electroluminescence spectrum of the OLED device prepared using the compound of the present invention has an extremely narrow half-peak width, a small concentration dependence, and exhibits a significant multiple resonance effect, thereby greatly improving the efficiency, stability and evaporation window width of the device, which can meet the current requirements of panel manufacturers for high-performance materials and show good application prospects. DETAILED DESCRIPTION

[0065] The specific preparation method of the above-mentioned novel compound of the present invention will be described in detail below using a plurality of synthesis examples as examples, but the preparation method of the present invention is not limited to these synthesis examples.

[0066] Various chemicals used in the present invention, such as petroleum ether, tert-butylbenzene, ethyl acetate, sodium sulfate, toluene, dichloromethane, potassium carbonate, boron tribromide, N,N-diisopropylethylamine, reaction intermediates, and other basic chemical raw materials, were purchased from Shanghai Titan Technology Co., Ltd. and Xilong Chemical Co., Ltd. The mass spectrometer used to determine the following compounds was a ZAB-HS mass spectrometer (manufactured by Micromass, UK).

[0067] The following is a brief description of the synthesis method of the compound of the present invention. First, n-butyl lithium or tert-butyl lithium is used to synthesize X 1 、X 2 、X 3 With X 4 The hydrogen and Cl atoms between / on the ions are ortho-metallated. Subsequently, boron tribromide is added for lithium-boron metal exchange, and a Bronsted base such as N,N-diisopropylethylamine is added to carry out a tandem Bora-Friedel-Crafts reaction to obtain the target product.

[0068]

[0069] More specifically, the synthesis methods of representative specific compounds of the present invention are given below.

[0070] Synthesis Example

[0071] Synthesis Example 1:

[0072]

[0073] Synthesis of compound S-7:

[0074] Synthesis of compound S-7-2

[0075]

[0076] In a three-necked flask, under nitrogen protection, 0.01 mol of S-7-1, 0.025 mol of 3,6-di-tert-butylcarbazole, and 150 ml of toluene were added and stirred, and then 5×10 -5 mol Pd2(dba)3, 0.03 mol sodium tert-butoxide, reflux for 12 hours, sampling the plate, showing no brominated product remaining, indicating complete reaction; naturally cool to room temperature, filter, and evaporate the filtrate until no fraction remains. Pass it through a neutral silica gel column (developing solvent: dichloromethane and petroleum ether) to obtain the target compound S-7-2 (9.22 g, 73% yield, HPLC analysis purity 99.56%) as a white powder.

[0077] Synthesis of compound S-7

[0078]

[0079] Under a nitrogen atmosphere, 0.03 mol of BBr3 was added to a 0.01 mol solution of S-7-2 in o-dichlorobenzene (100 mL). The reaction was continued at 190°C for 24 hours before cessation. The solvent was evaporated in vacuo and the product was passed through a silica gel column (developing solvent: ethyl acetate:petroleum ether = 50:1) to obtain the target compound S-7 (0.64 g, 5% yield, HPLC purity 99.42%) as a green solid. MALDI-TOF-MS results: Molecular ion peak: 1271.55. Elemental analysis: Calculated values: C, 86.90; H, 7.85; B, 0.85; N, 4.41 (%); Found values: C, 86.80; H, 7.85; B, 0.85; N, 4.51 (%).

[0080] Synthesis Example 2:

[0081]

[0082] Synthesis of compound S-11

[0083] Synthesis of compound S-11-2

[0084]

[0085] Synthesis of compound S-11

[0086] In a three-necked flask, under nitrogen protection, 0.01 mol of S-11-1, 0.025 mol of triphenylboric acid, and 150 ml of a tetrahydrofuran-water (volume ratio 3:1) mixed solution were added, stirred, and then 6×10 -5mol Pd(Pph3)4, 0.03 mol potassium carbonate, reflux for 12 hours, the reaction is complete; naturally cooled to room temperature, filtered, the filtrate is rotary evaporated until no fraction is left, and passed through a neutral silica gel column (developing solvent: dichloromethane and petroleum ether) to obtain the target compound S-11-2 (12.50 g, 90% yield, HPLC analysis purity 99.36%) as a white powder.

[0087]

[0088] This example is essentially the same as the synthesis of compound S-7, except that S-7-2 is replaced with an equal amount of S-11-2. The target compound S-11 (1.68 g, 12% yield, 99.26% purity by HPLC analysis) was obtained as a green solid. MALDI-TOF-MS results: Molecular ion peak: 1396.55. Elemental analysis: Calculated: C, 88.59; H, 7.90; B, 0.38; N, 1.99; S, 1.14 (%); Found: C, 88.39; H, 7.80; B, 0.58; N, 1.99; S, 1.24 (%).

[0089] Synthesis Example 3:

[0090]

[0091] Synthesis of compound S-13

[0092] Synthesis of compound S-13-2

[0093]

[0094] In a three-necked flask, under nitrogen, 0.01 mol of S-13-1, 0.01 mol of NBS, and 223 ml of chloroform were added. The mixture was allowed to react at room temperature for 12 hours until the reaction was complete. The solvent was then evaporated and the mixture was passed through a neutral silica gel column (developing solvents: dichloromethane and petroleum ether) to obtain the target compound S-11-2 (6.80 g, 80% yield, 99.46% purity by HPLC) as a white powder.

[0095] Synthesis of compound S-13

[0096]

[0097] In a three-necked flask, under nitrogen protection, 5 mmol of S-13-2, 10 mmol of 9-phenyl-carbazolephenylboronic acid, and 40 mL of tetrahydrofuran / water (volume ratio 3:1) were added and stirred. Then, 0.15 mmol of Pd(PPh3)4 and 20 mmol of potassium carbonate were added and refluxed for 12 hours. A sampling plate showed that no brominated product remained, indicating that the reaction was complete. The product was naturally cooled to room temperature and filtered. The filtrate was rotary evaporated until no fraction remained and passed through a neutral silica gel column (developing solvent: dichloromethane and petroleum ether) to obtain the target compound S-13 (3.04 g, 60% yield, HPLC analysis purity 99.66%) as a green powder. MALDI-TOF-MS results: Molecular ion peak: 1014.62 Elemental analysis results: Theoretical value: C, 87.64; H, 7.16; B, 1.07; N, 4.14 (%); Experimental value: C, 87.54; H, 7.26; B, 1.37; N, 3.84 (%).

[0098] Synthesis Example 4:

[0099]

[0100] Synthesis of compound S-25

[0101] Synthesis of compound S-25

[0102]

[0103] This example is essentially the same as the synthesis of compound S-13, except that S-13-2 is replaced with an equal amount of S-25-1. The target compound S-25-2 (2.91 g, 66% yield, 99.63% purity by HPLC analysis) is a green solid. MALDI-TOF-MS results: Molecular ion peak: 881.62 Elemental analysis results: Theoretical values: C, 87.15; H, 6.86; B, 1.23; N, 4.76 (%); Found values: C, 87.05; H, 6.87; B, 1.33; N, 4.75 (%). Chemical Formula: C64H60BN3

[0104] Synthesis Example 5:

[0105]

[0106] Synthesis of compound S-26

[0107] Synthesis of compound S-26-2

[0108]

[0109] This example is essentially the same as the synthesis of compound S-7-2, except that S-7-1 is replaced with an equal amount of S-26-1, and 3,6-di-tert-butylcarbazole is replaced with an equal amount of an indolecarbazole derivative. The target compound S-26-2 (9.47 g, 84% yield, 99.25% purity by HPLC) is obtained as a white solid.

[0110] Synthesis of compound S-26

[0111]

[0112] This example is essentially the same as the synthesis of compound S-7, except that S-7-2 is replaced with an equal amount of S-26-2. The target compound S-26 (2.51 g, 22% yield, 99.23% purity by HPLC analysis) was obtained as a green solid. MALDI-TOF-MS results: Molecular ion peak: 1135.42. Elemental analysis: Calculated: C, 86.68; H, 6.21; B, 0.95; N, 6.16 (%); Found: C, 86.78; H, 6.21; B, 0.95; N, 6.06 (%).

[0113] Synthesis Example 6:

[0114]

[0115] Synthesis of compound S-151

[0116] Synthesis of compound S-151-2

[0117]

[0118] This example is essentially the same as the synthesis of compound S-7-2, except that S-7-1 is replaced with an equal amount of S-151-1. The target compound S-151-2 (10.89 g, 86% yield, 99.53% purity by HPLC) is obtained as a white solid.

[0119] Synthesis of compound S-52

[0120]

[0121] This example is essentially the same as the synthesis of compound S-7, except that S-7-2 is replaced with an equal amount of S-151-2. The target compound S-151 (4.59 g, 36% yield, 99.23% purity by HPLC analysis) was obtained as a green solid. MALDI-TOF-MS results: Molecular ion peak: 1275.02. Elemental analysis: Calculated: C, 86.62; H, 8.14; B, 0.85; N, 4.39 (%); Found: C, 86.52; H, 8.24; B, 0.86; N, 4.38 (%).

[0122] Synthesis Example 7:

[0123]

[0124] Synthesis of compound S-199

[0125] Synthesis of compound S-199-2

[0126]

[0127] This example is essentially the same as the synthesis of compound S-7-2, except that S-7-1 is replaced with an equal amount of S-199-1, and 3,6-di-tert-butylcarbazole is replaced with an equal amount of a spirofluorene derivative. The target compound S-199-2 (10.89 g, 79% yield, 99.65% purity by HPLC) is obtained as a white solid.

[0128] Synthesis of compound S-199

[0129]

[0130] This example is essentially the same as the synthesis of compound S-7, except that S-7-2 is replaced with an equal amount of S-199-2. The target compound S-199 (3.18 g, 23% yield, 99.33% purity by HPLC analysis) was obtained as a green solid. MALDI-TOF-MS results: Molecular ion peak: 1378.62. Elemental analysis: Calculated: C, 88.80; H, 6.36; B, 0.78; N, 4.06 (%); Found: C, 88.70; H, 6.46; B, 0.75; N, 4.09 (%).

[0131] Synthesis Example 8:

[0132]

[0133] Synthesis of compound S-189

[0134] Synthesis of compound S-189-2

[0135]

[0136] Synthesis of compound S-189-2

[0137] In a three-necked flask, under nitrogen protection, 0.01 mol of S-189-1, 0.025 mol of triphenylboric acid, and 150 ml of a tetrahydrofuran-water (volume ratio 3:1) mixed solution were added, stirred, and then 6×10 -5 mol Pd(Pph3)4, 0.03 mol potassium carbonate, reflux for 12 hours, the reaction is complete; naturally cool to room temperature, filter, and evaporate the filtrate until there is no fraction. Pass it through a neutral silica gel column (developing solvent: dichloromethane and petroleum ether) to obtain the target compound S-189-2 (12.50 g, 90% yield, HPLC analysis purity 99.22%) as a white powder.

[0138]

[0139] This example is essentially the same as the synthesis of compound S-7, except that S-7-2 is replaced with an equal amount of S-189-2. The target compound S-189 (0.84 g, 6% yield, 99.56% purity by HPLC analysis) was obtained as a green solid. MALDI-TOF-MS results: Molecular ion peak: 1396.55. Elemental analysis: Calculated: C, 88.59; H, 7.90; B, 0.38; N, 1.99; S, 1.14 (%); Found: C, 88.39; H, 7.80; B, 0.68; N, 1.99; S, 1.14 (%).

[0140] Synthesis Example 9:

[0141]

[0142] Synthesis of compound S-223

[0143] Synthesis of compound S-223-2

[0144]

[0145] This example is essentially the same as the synthesis of compound S-7-2, except that S-7-1 is replaced with an equal amount of S-223-1. The target compound S-223-2 (9.64 g, 85% yield, 99.23% purity by HPLC) is obtained as a white solid.

[0146] Synthesis of compound S-223

[0147]

[0148] This example is essentially the same as the synthesis of compound S-7, except that S-7-2 is replaced with an equal amount of S-223-2. The target compound S-223 (2.97 g, 26% yield, 99.53% purity by HPLC analysis) was obtained as a green solid. MALDI-TOF-MS results: Molecular ion peak: 1142.62. Elemental analysis: Calculated: C, 86.21; H, 7.76; B, 0.95; N, 3.68; O, 1.40 (%); Found: C, 86.21; H, 7.66; B, 0.95; N, 3.78; O, 1.40 (%).

[0149] Synthesis Example 10:

[0150]

[0151] Synthesis of compound S-245

[0152]

[0153] This example is essentially the same as the synthesis of compound S-189-2, except that S-189-1 is replaced with an equal amount of S-245-1. The target compound S-245 (6.36 g, 72% yield, 99.55% purity by HPLC analysis) is a green solid. MALDI-TOF-MS results: Molecular ion peak 882.57. Elemental analysis: Calculated: C, 84.33; H, 7.65; B, 1.22; N, 3.17; S, 3.63 (%); Found: C, 84.53; H, 7.55; B, 1.12; N, 3.37; S, 3.43 (%).

[0154] Synthesis Example 11:

[0155]

[0156] Synthesis of compound S-232

[0157] Synthesis of compound S-232-2

[0158]

[0159] This example is essentially the same as the synthesis of compound S-13-2, except that S-13-1 is replaced with an equal amount of S-232-1. The target compound S-232-2 (6.05 g, 82% yield, 99.63% purity by HPLC) is obtained as a white powder.

[0160] Synthesis of compound S-232

[0161]

[0162] This example is essentially the same as the synthesis of compound S-13, except that S-13-2 is replaced with an equal amount of S-232-2. The target compound S-232 (4.04 g, 89% yield, 99.62% purity by HPLC analysis) is a green powder. MALDI-TOF-MS results: Molecular ion peak: 891.32. Elemental analysis: Calculated: C, 82.23; H, 6.67; B, 1.21; N, 6.29; S, 3.60 (%); Found: C, 82.33; H, 6.57; B, 1.31; N, 6.29; S, 3.50 (%).

[0163] Synthesis Example 12:

[0164]

[0165] Synthesis of compound S-292

[0166] Synthesis of compound S-292-2

[0167]

[0168] This example is essentially the same as the synthesis of compound S-7-2, except that S-7-1 is replaced with an equal amount of S-292-1. The target compound S-292-2 (11.78 g, 85% yield, 99.53% purity by HPLC) is obtained as a white solid.

[0169] Synthesis of compound S-292

[0170]

[0171] This example is essentially the same as the synthesis of compound S-7, except that S-7-2 is replaced with an equal amount of S-292-2. The target compound S-292 (4.32 g, 31% yield, 99.48% purity by HPLC analysis) was obtained as a green solid. MALDI-TOF-MS results: Molecular ion peak: 1394.62. Elemental analysis: Calculated: C, 87.77; H, 7.44; B, 0.77; N, 4.01 (%); Found: C, 87.67; H, 7.54; B, 0.67; N, 4.11 (%).

[0172] The technical effects and advantages of the present invention are demonstrated and verified by applying the compound of the present invention to an organic electroluminescent device to test its actual performance.

[0173] An organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer located between the two electrodes. The organic material layer can be divided into multiple regions, for example, the organic material layer can include a hole transport region, a light emitting layer, and an electron transport region.

[0174] The anode material can be made of transparent conductive oxide materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), and any combination thereof. The cathode material can be made of metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof.

[0175] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including single-layer hole transport layers containing only one compound and single-layer hole transport layers containing multiple compounds. The hole transport region can also be a multilayer structure comprising at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0176] The material of the hole transport region can be selected from but not limited to phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, etc.

[0177] The light-emitting layer includes a luminescent dye (i.e., a dopant) that can emit light at different wavelengths, and may also include a host material. The light-emitting layer can be a monochromatic light-emitting layer that emits a single color, such as red, green, or blue. Multiple monochromatic light-emitting layers of different colors can be arranged in a planar pattern according to a pixel pattern, or they can be stacked together to form a multi-color light-emitting layer. When light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single-color light-emitting layer that can simultaneously emit different colors, such as red, green, and blue.

[0178] The electron transport region can be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region can also be a multi-layer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0179] The specific process for preparing an organic electroluminescent device is as follows: an anode, a hole transport layer, an organic light-emitting layer, an electron transport layer, and a cathode are sequentially deposited on a substrate, followed by encapsulation. The organic light-emitting layer is formed by co-evaporating a wide bandgap material source, an electron donor material source, an electron acceptor material source, and a resonant TADF material source.

[0180] Specifically, the method for preparing an organic electroluminescent device of the present invention comprises the following steps:

[0181] 1. The glass plate coated with the anode material was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent, baked in a clean environment to completely remove water, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0182] 2. Place the glass plate with the anode in a vacuum chamber and evacuate to 1×10 -5 ~9×10 -3 Pa, vacuum evaporating a hole injection material on the anode layer to form a hole injection layer at a rate of 0.1-0.5 nm / s;

[0183] 3. Vacuum evaporate the hole transport material on the hole injection layer to form a hole transport layer at a rate of 0.1-0.5 nm / s.

[0184] 4. Vacuum evaporate the electron blocking layer on the hole transport layer at a rate of 0.1-0.5 nm / s;

[0185] 5. Vacuum-depositing the organic light-emitting layer of the device on the electron blocking layer. The organic light-emitting layer materials include a host material and a TADF dye. Using a multi-source co-evaporation method, the evaporation rate of the host material, the evaporation rate of the sensitizer material, and the evaporation rate of the dye are adjusted to achieve a preset doping ratio of the dye.

[0186] 6. Vacuum-deposit a hole blocking layer on the organic light-emitting layer at a rate of 0.1-0.5 nm / s;

[0187] 7. Vacuum evaporating the electron transport material of the device on the hole blocking layer to form an electron transport layer at a rate of 0.1-0.5 nm / s;

[0188] 8. LiF was vacuum evaporated at 0.1-0.5 nm / s on the electron transport layer as the electron injection layer, and Al was vacuum evaporated at 0.5-1 nm / s as the cathode of the device.

[0189] An embodiment of the present invention further provides a display device comprising the organic electroluminescent device described above. Specifically, the display device may be an OLED display, or any other display-capable product or component incorporating the display device, such as a television, digital camera, mobile phone, or tablet computer. The advantages of this display device over existing technologies are the same as those of the organic electroluminescent device described above, and are not further elaborated here.

[0190] The organic electroluminescent device of the present invention is further described below through specific examples.

[0191] Device Example 1

[0192] The structure of the organic electroluminescent device prepared in this embodiment is as follows:

[0193] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:1wt%S-7(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0194] Among them, the anode material is ITO; the hole injection layer material is HI, the total thickness is generally 5-30nm, and the present embodiment is 10nm; the hole transport layer material is HT, the total thickness is generally 5-500nm, and the present embodiment is 40nm; Host is the main material of the organic light-emitting layer with a wide band gap, the compound S-7 of the present invention is a dye and the doping concentration is 1wt%, the thickness of the organic light-emitting layer is generally 1-200nm, and the present embodiment is 30nm; the electron transport layer material is ET, the thickness is generally 5-300nm, and the present embodiment is 30nm; LiF (0.5nm) and metal aluminum (150nm) are selected as the electron injection layer and cathode materials.

[0195] A DC voltage was applied to the organic electroluminescent device D1 prepared in this example, and the luminous flux of 10 cd / m 2 The characteristics of the light emission are blue-green light emission with a wavelength of 488nm, a half-peak width of 22nm, CIE color coordinates (x, y) = (0.11, 0.40), and an external quantum efficiency EQE of 28.8% (driving voltage is 2.8V).

[0196] Device Example 2

[0197] The preparation method is the same as that of device embodiment 1, except that the wide bandgap host material Host used in the light-emitting layer is replaced with a TADF host TD. The specific device structure is as follows:

[0198] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:1wt%S-7(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0199] The device performance of the organic electroluminescent device D2 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue-green light emission with a wavelength of 488nm, a half-peak width of 22nm, CIE color coordinates (x, y) = (0.10, 0.41), and an external quantum efficiency EQE of 37.2% (driving voltage is 2.8V).

[0200] Device Example 3

[0201] The preparation method is the same as that of device embodiment 2, except that the concentration of the dye in the light-emitting layer is increased to 20%. The specific device structure is as follows:

[0202] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:20wt%S-7(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0203] The performance of the organic electroluminescent device D3 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are blue-green light emission with a wavelength of 491nm, a half-peak width of 22nm, CIE color coordinates (x, y) = (0.10, 0.41), and an external quantum efficiency EQE of 36.3% (driving voltage is 2.8V).

[0204] Device Example 4

[0205] The preparation method is the same as that of device embodiment 1, except that the light-emitting layer contains only dye. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / S-7 (30nm) / HBL (10nm) ET (30nm) / LiF / Al (150nm)

[0206] The device performance of the organic electroluminescent device D4 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue-green light emission with a wavelength of 490nm, a half-peak width of 21nm, CIE color coordinates (x, y) = (0.10, 0.42), and an external quantum efficiency EQE of 18.4% (driving voltage is 2.8V).

[0207] Device Example 5

[0208] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by S-13 instead of S-7. The device structure is as follows:

[0209] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:1wt%S-13(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0210] The performance of the organic electroluminescent device D5 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are blue-green light emission with a wavelength of 504nm, a half-maximum width of 26nm, CIE color coordinates (x, y) = (0.12, 0.60), and an external quantum efficiency EQE of 29.2% (driving voltage is 2.8V).

[0211] Device Example 6

[0212] The preparation method is the same as that of device example 1, except that the wide bandgap host material Host in the light-emitting layer is replaced with a TADF host TD, and the dye is replaced from S-7 to S-13. The device structure is as follows:

[0213] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:1wt%S-13(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0214] The performance of the organic electroluminescent device D6 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are blue-green light emission with a wavelength of 504nm, a half-peak width of 26nm, CIE color coordinates (x, y) = (0.12, 0.60), and an external quantum efficiency EQE of 36.2% (driving voltage is 2.8V).

[0215] Device Example 7

[0216] The preparation method is the same as that of device Example 6, except that the concentration of the dye in the light-emitting layer is increased to 20%. The specific device structure is as follows:

[0217] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:20wt%S-13(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0218] The performance of the organic electroluminescent device D7 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are blue-green light emission with a wavelength of 506nm, a half-peak width of 29nm, CIE color coordinates (x, y) = (0.12, 0.62), and an external quantum efficiency EQE of 35.1% (driving voltage is 2.8V).

[0219] Device Example 8

[0220] The preparation method is the same as that of device Example 5, except that the light-emitting layer contains only dye. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / S-13 (30nm) / HBL (10nm) ET (30nm) / LiF / Al (150nm)

[0221] The performance of the organic electroluminescent device D8 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 512nm, a half-peak width of 35nm, CIE color coordinates (x, y) = (0.15, 0.65), and an external quantum efficiency EQE of 19.2% (driving voltage is 2.8V).

[0222] Device Example 9

[0223] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by S-25 instead of S-7. The device structure is as follows:

[0224] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:1wt%S-25(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0225] The performance of the organic electroluminescent device D9 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 468nm, a half-peak width of 25nm, CIE color coordinates (x, y) = (0.12, 0.19), and an external quantum efficiency EQE of 26.4% (driving voltage is 2.8V).

[0226] Device Example 10

[0227] The preparation method is the same as that of device example 1, except that the wide bandgap host material Host in the light-emitting layer is replaced with a TADF host TD, and the dye is replaced from S-7 to S-25. The device structure is as follows:

[0228] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:1wt%S-25(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0229] The performance of the organic electroluminescent device D10 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 470nm, a half-peak width of 25nm, CIE color coordinates (x, y) = (0.12, 0.19), and an external quantum efficiency EQE of 35.4% (driving voltage is 2.8V).

[0230] Device Example 11

[0231] The preparation method is the same as that of device example 10, except that the concentration of the dye in the light-emitting layer is increased to 20%. The specific device structure is as follows:

[0232] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:20wt%S-25(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0233] The performance of the organic electroluminescent device D11 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 472nm, a half-peak width of 27nm, CIE color coordinates (x, y) = (0.13, 0.19), and an external quantum efficiency EQE of 33.4% (driving voltage is 2.8V).

[0234] Device Example 12

[0235] The preparation method is the same as that of device Example 9, except that the light-emitting layer contains only dye. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / S-25 (30nm) / HBL (10nm) ET (30nm) / LiF / Al (150nm)

[0236] The device performance of the organic electroluminescent device D12 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 475nm, a half-maximum width of 33nm, CIE color coordinates (x, y) = (0.12, 0.20), and an external quantum efficiency EQE of 16.4% (driving voltage is 2.8V).

[0237] Device Example 13

[0238] The preparation method is the same as that of device Example 1, except that the dye used in the light-emitting layer is replaced by S-151 instead of S-7. The device structure is as follows:

[0239] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:1wt%S-151(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0240] The device performance of the organic electroluminescent device D13 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 458nm, a half-maximum width of 23nm, CIE color coordinates (x, y) = (0.12, 0.07), and an external quantum efficiency EQE of 21.4% (driving voltage is 2.8V).

[0241] Device Example 14

[0242] The preparation method is the same as that of device example 1, except that the wide bandgap host material Host in the light-emitting layer is replaced with a TADF host TD, and the dye is replaced from S-7 with S-151. The device structure is as follows:

[0243] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:1wt%S-151(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0244] The device performance of the organic electroluminescent device D14 prepared in this example is measured as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 460nm, a half-maximum width of 23nm, CIE color coordinates (x, y) = (0.12, 0.07), and an external quantum efficiency EQE of 33.2% (driving voltage is 2.8V).

[0245] Device Example 15

[0246] The preparation method is the same as that of device Example 14, except that the concentration of the dye in the light-emitting layer is increased to 20%. The specific device structure is as follows:

[0247] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:20wt%S-151(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0248] The performance of the organic electroluminescent device D15 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 462nm, a half-maximum width of 23nm, CIE color coordinates (x, y) = (0.13, 0.07), and an external quantum efficiency EQE of 32.5% (driving voltage is 2.8V).

[0249] Device Example 16

[0250] The preparation method is the same as that of device Example 13, except that the light-emitting layer contains only dye. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / S-151 (30nm) / HBL (10nm) ET (30nm) / LiF / Al (150nm)

[0251] The performance of the organic electroluminescent device D16 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 462nm, a half-peak width of 22nm, CIE color coordinates (x, y) = (0.12, 0.07), and an external quantum efficiency EQE of 17.1% (driving voltage is 2.8V).

[0252] Device Example 17

[0253] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by S-199 instead of S-7. The device structure is as follows:

[0254] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:1wt%S-199(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0255] The device performance of the organic electroluminescent device D17 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 456nm, a half-maximum width of 26nm, CIE color coordinates (x, y) = (0.13, 0.09), and an external quantum efficiency EQE of 23.4% (driving voltage is 3.0V).

[0256] Device Example 18

[0257] The preparation method is the same as that of device example 1, except that the wide bandgap host material Host in the light-emitting layer is replaced with a TADF host TD, and the dye is replaced from S-7 to S-199. The device structure is as follows:

[0258] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:1wt%S-199(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0259] The device performance of the organic electroluminescent device D18 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 458nm, a half-maximum width of 26nm, CIE color coordinates (x, y) = (0.13, 0.09), and an external quantum efficiency EQE of 33.4% (driving voltage 3.0V).

[0260] Device Example 19

[0261] The preparation method is the same as that of device Example 18, except that the concentration of the dye in the light-emitting layer is increased to 20%. The specific device structure is as follows:

[0262] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:20wt%S-199(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0263] The performance of the organic electroluminescent device D19 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 460nm, a half-maximum width of 26nm, CIE color coordinates (x, y) = (0.13, 0.09), and an external quantum efficiency EQE of 31.6% (driving voltage 3.0V).

[0264] Device Example 20

[0265] The preparation method is the same as that of device Example 17, except that the light-emitting layer contains only dye. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / S-199 (30nm) / HBL (10nm) ET (30nm) / LiF / Al (150nm)

[0266] The device performance of the organic electroluminescent device D20 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 460nm, a half-peak width of 25nm, CIE color coordinates (x, y) = (0.12, 0.08), and an external quantum efficiency EQE of 14.4% (driving voltage is 3.0V).

[0267] Device Example 21

[0268] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by S-189 instead of S-7. The device structure is as follows:

[0269] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:1wt%S-189(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0270] The device performance of the organic electroluminescent device D21 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 472nm, a half-peak width of 26nm, CIE color coordinates (x, y) = (0.13, 0.20), and an external quantum efficiency EQE of 25.2% (driving voltage is 2.8V).

[0271] Device Example 22

[0272] The preparation method is the same as that of device example 1, except that the wide bandgap host material Host in the light-emitting layer is replaced with a TADF host TD, and the dye is replaced from S-7 to S-189. The device structure is as follows:

[0273] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:1wt%S-189(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0274] The device performance of the organic electroluminescent device D22 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 472nm, a half-maximum width of 26nm, CIE color coordinates (x, y) = (0.13, 0.19), and an external quantum efficiency EQE of 38.2% (driving voltage is 2.8V).

[0275] Device Example 23

[0276] The preparation method is the same as that of device Example 22, except that the concentration of the dye in the light-emitting layer is increased to 20%. The specific device structure is as follows:

[0277] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:20wt%S-189(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0278] The device performance of the organic electroluminescent device D23 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 474 nm, a half-maximum width of 26 nm, CIE color coordinates (x, y) = (0.13, 0.20), and an external quantum efficiency EQE of 37.0% (driving voltage is 2.8 V).

[0279] Device Example 24

[0280] The preparation method is the same as that of device Example 21, except that the light-emitting layer contains only dye. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / S-223 (30nm) / HBL (10nm) ET (30nm) / LiF / Al (150nm)

[0281] The device performance of the organic electroluminescent device D24 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 472nm, a half-peak width of 25nm, CIE color coordinates (x, y) = (0.13, 0.19), and an external quantum efficiency EQE of 17.3% (driving voltage is 2.8V).

[0282] Device Example 25

[0283] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by S-223 instead of S-7. The device structure is as follows:

[0284] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:1wt%S-223(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0285] The performance of the organic electroluminescent device D25 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2The characteristics of the light emission are blue-violet light emission with a wavelength of 410nm, a half-peak width of 26nm, CIE color coordinates (x, y) = (0.16, 0.02), and an external quantum efficiency EQE of 22.2% (driving voltage is 3.2V).

[0286] Device Example 26

[0287] The preparation method is the same as that of device example 1, except that the wide bandgap host material Host in the light-emitting layer is replaced with a TADF host TD, and the dye is replaced from S-7 to S-223. The device structure is as follows:

[0288] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:1wt%S-223(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0289] The performance of the organic electroluminescent device D26 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are blue-violet light emission with a wavelength of 411 nm, a half-peak width of 26 nm, CIE color coordinates (x, y) = (0.16, 0.02), and an external quantum efficiency EQE of 29.2% (driving voltage is 3.2 V).

[0290] Device Example 27

[0291] The preparation method is the same as that of device Example 26, except that the concentration of the dye in the light-emitting layer is increased to 20%. The specific device structure is as follows:

[0292] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:20wt%S-223(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0293] The device performance of the organic electroluminescent device D27 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue-violet light emission with a wavelength of 410nm, a half-peak width of 26nm, CIE color coordinates (x, y) = (0.16, 0.02), and an external quantum efficiency EQE of 28.6% (driving voltage is 3.2V).

[0294] Device Example 28

[0295] The preparation method is the same as that of device Example 25, except that the light-emitting layer contains only dye. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / S-223 (30nm) / HBL (10nm) ET (30nm) / LiF / Al (150nm)

[0296] The device performance of the organic electroluminescent device D28 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue-violet light emission with a wavelength of 410nm, a half-peak width of 25nm, CIE color coordinates (x, y) = (0.16, 0.02), and an external quantum efficiency EQE of 12.5% ​​(driving voltage is 3.2V).

[0297] Device Example 29

[0298] The preparation method is the same as that of device Example 1, except that the dye used in the light-emitting layer is replaced by S-292 instead of S-7. The device structure is as follows:

[0299] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:1wt%S-292(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0300] The device performance of the organic electroluminescent device D29 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 527nm, a half-peak width of 28nm, CIE color coordinates (x, y) = (0.27, 0.68), and an external quantum efficiency EQE of 22.4% (driving voltage is 2.8V).

[0301] Device Example 30

[0302] The preparation method is the same as that of device example 1, except that the wide bandgap host material Host in the light-emitting layer is replaced with a TADF host TD, and the dye is replaced from S-7 with S-292. The device structure is as follows:

[0303] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:1wt%S-292(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0304] The D30 performance of the organic electroluminescent device prepared in this example is as follows: DC voltage is applied and the D30 of the device is measured at 10 cd / m 2The characteristics of the light emission are green light with a wavelength of 527nm, a half-peak width of 28nm, CIE color coordinates (x, y) = (0.27, 0.69), and an external quantum efficiency EQE of 39.4% (driving voltage is 2.8V).

[0305] Device Example 31

[0306] The preparation method is the same as that of device example 30, except that the concentration of the dye in the light-emitting layer is increased to 20%. The specific device structure is as follows:

[0307] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:20wt%S-292(30nm) / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0308] The device performance of the organic electroluminescent device D31 prepared in this example is measured as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of light emission are green light emission with a wavelength of 527 nm, a half-peak width of 28 nm, CIE color coordinates (x, y) = (0.27, 0.68), and an external quantum efficiency EQE of 38.0% (driving voltage is 2.8 V).

[0309] Device Example 32

[0310] The preparation method is the same as that of device Example 291, except that the light-emitting layer contains only dye. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / S-292 (30nm) / HBL (10nm) ET (30nm) / LiF / Al (150nm)

[0311] The device performance of the organic electroluminescent device D32 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 530 nm, a half-peak width of 30 nm, CIE color coordinates (x, y) = (0.28, 0.68), and an external quantum efficiency EQE of 20.0% (driving voltage 2.8 V).

[0312] Comparative Device Example 1

[0313] The preparation method is the same as that of device Example 1, except that the compound S-7 of the present invention used in the light-emitting layer is replaced by the compound P1 in the prior art. The specific device structure is as follows:

[0314] ITO / HI(10nm) / HT(40nm) / Host:1wt%P1(30nm) / ET(30nm) / LiF / Al(150nm)

[0315] The device performance of the organic electroluminescent device DD1 prepared in this example is measured as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue-green light emission with a wavelength of 488nm, a half-maximum width of 32nm, CIE color coordinates (x, y) = (0.13, 0.42), and an external quantum efficiency EQE of 18.5% (driving voltage 3.0V).

[0316] Comparative Device Example 2

[0317] The preparation method is the same as that of device Example 2, except that the compound S-7 of the present invention used in the light-emitting layer is replaced by the compound P1 in the prior art. The specific device structure is as follows:

[0318] ITO / HI(10nm) / HT(40nm) / TD:1wt%P1(30nm) / ET(30nm) / LiF / Al(150nm)

[0319] The device performance of the organic electroluminescent device DD2 prepared in this example is measured as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue-green light emission with a wavelength of 488nm, a half-maximum width of 29nm, CIE color coordinates (x, y) = (0.13, 0.40), and an external quantum efficiency EQE of 27.5% (driving voltage 3.0V).

[0320] Comparative Device Example 3

[0321] The preparation method is the same as that of comparative device Example 2, except that the concentration of the dye in the light-emitting layer is increased to 20%. The specific device structure is as follows:

[0322] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:20wt%P1(30nm / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0323] The device performance of the organic electroluminescent device DD3 prepared in this example is measured as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue-green light emission with a wavelength of 496nm, a half-maximum width of 37nm, CIE color coordinates (x, y) = (0.13, 0.46), and an external quantum efficiency EQE of 18.1% (driving voltage 3.0V).

[0324] Comparative Device Example 4

[0325] The preparation method is the same as that of the comparative device Example 1, except that the light-emitting layer contains only dye. The specific structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / P1 (30nm) / HBL (10nm) ET (30nm) / LiF / Al (150nm)

[0326] The device performance of the organic electroluminescent device DD4 prepared in this example is measured as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 507nm, a half-maximum width of 48nm, CIE color coordinates (x, y) = (0.26, 0.57), and an external quantum efficiency EQE of 9.5% (driving voltage 3.0V).

[0327] Comparative Device Example 5

[0328] The preparation method is the same as that of device example 1, except that the compound S-7 of the present invention used in the light-emitting layer is replaced by the compound P2 in the prior art. The specific device structure is as follows:

[0329] ITO / HI(10nm) / HT(40nm) / Host:1wt%P2(30nm) / ET(30nm) / LiF / Al(150nm)

[0330] The device performance of the organic electroluminescent device DD5 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 469nm, a half-maximum width of 28nm, CIE color coordinates (x, y) = (0.13, 0.12), and an external quantum efficiency EQE of 13.5% (driving voltage is 3.4V).

[0331] Comparative Device Example 6

[0332] The preparation method is the same as that of device Example 2, except that the compound S-7 of the present invention used in the light-emitting layer is replaced by the compound P2 in the prior art. The specific device structure is as follows:

[0333] ITO / HI(10nm) / HT(40nm) / TD:1wt%P2(30nm) / ET(30nm) / LiF / Al(150nm)

[0334] The device performance of the organic electroluminescent device DD6 prepared in this example is measured as follows: DC voltage is applied and the 10 cd / m 2The characteristics of the light emission are blue light emission with a wavelength of 468nm, a half-peak width of 28nm, CIE color coordinates (x, y) = (0.13, 0.12), and an external quantum efficiency EQE of 18.4% (driving voltage is 3.3V).

[0335] Comparative Device Example 7

[0336] The preparation method is the same as that of comparative device Example 6, except that the concentration of the dye in the light-emitting layer is increased to 20%. The specific device structure is as follows:

[0337] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / TD:20wt%P2(30nm / HBL(10nm)ET(30nm) / LiF / Al(150nm)

[0338] The device performance of the organic electroluminescent device DD7 prepared in this example is measured as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 470nm, a half-maximum width of 36nm, CIE color coordinates (x, y) = (0.14, 0.15), and an external quantum efficiency EQE of 12.6% (driving voltage 3.3V).

[0339] Comparative Device Example 8

[0340] The preparation method is the same as that of the comparative device Example 5, except that the light-emitting layer contains only dye. The specific structure is as follows: ITO / HI (10nm) / HT (30nm) / EBL (10nm) / P2 (30nm) / HBL (10nm) ET (30nm) / LiF / Al (150nm)

[0341] The device performance of the organic electroluminescent device DD8 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue-green light emission with a wavelength of 480nm, a half-maximum width of 48nm, CIE color coordinates (x, y) = (0.13, 0.29), and an external quantum efficiency EQE of 8.1% (driving voltage 3.3V).

[0342] The structural formulas of the various organic materials used in the above embodiments are as follows:

[0343]

[0344]

[0345]

[0346] The specific performance data of the organic electroluminescent devices D1 to D32 and devices DD1 and DD8 prepared in the above device embodiments are shown in Table 1 below.

[0347] Table 1:

[0348]

[0349]

[0350] The above experimental data show that the compounds of the present invention can effectively inhibit the broadening of the spectrum and the reduction of luminous efficiency of the compounds at high concentrations by introducing a carbocyclic group or heterocyclic group represented by A coated with a large steric hindrance group into the molecular structure. Compared with the comparative example devices prepared using the prior art compounds, the devices using the compounds of the present invention have extremely narrow half-peak width and smaller concentration dependence characteristics, which can meet the current requirements of panel manufacturers for high-performance materials and have good application prospects.

[0351] Although the present invention has been described with reference to the embodiments, it is not limited to these embodiments. Those skilled in the art may make various modifications and improvements based on the inventive concept, and the appended claims outline the scope of the invention. Those skilled in the art will appreciate that other variations or modifications may be made based on the above description. It is not necessary and impossible to enumerate all possible embodiments here. Obvious variations or modifications arising therefrom remain within the scope of the present invention.

Claims

1. A compound having the structure shown in Formula (1-1) or Formula (1-2): In formula (1-1) and formula (1-2), A is represented by any one of the following structural formulas: in, R3 and R4 are independently hydrogen, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C2~C 60 Any of heteroaryl groups; Z is independently CR5, R5 is hydrogen, C1-C 10 Alkyl, substituted or unsubstituted C6~C 30 One of the aromatic groups; Z1-Z 10 Each of the R atoms is independently represented by CR, wherein each occurrence of R is the same or different and each occurrence of R is not hydrogen; R1 is not connected to the adjacent R or is connected by a single bond; R1 represents a substituted or unsubstituted C6~C 30 aryl; R represents hydrogen, deuterium, C1~C 10 Alkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; The substitution in the substituted or unsubstituted R1, R, R3, R4 and R5 mentioned above refers to a 10 Alkyl, C6~C 30 Aryl, C2~C 30 or a combination of two of the heteroaryl groups.

2. The compound of the general formula according to claim 1, characterized in that In formula (1-1) and (1-2): R1 is connected to the adjacent R through a single bond.

3. The compound of the general formula according to claim 1, wherein at least one of R3 and R4 is selected from the group consisting of the following bulky steric groups: terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, isoindolyl, carbazolyl, indenocarbazolyl, isoquinolyl, acridinyl, Phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, benzimidazolyl, naphthioimidazolyl, phenanthioimidazolyl, pyridinoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthioxazolyl, anthrazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, phenazinyl, phenothiazinyl, azacarbazolyl, benzocarbolyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4 -thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, methylphenyl, trimethylphenyl, or a combination of at least one of R3 and R4 selected from two of the above-mentioned bulky steric groups.

4. The compound of the general formula according to claim 1 or 2, characterized in that The Z1-Z8 are independently represented by CR, wherein R represents hydrogen, methyl, ethyl, isopropyl, or tert-butyl; The Z9-Z 10 R in each of N and CR is independently hydrogen, deuterium, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, quinolyl, furyl, thienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, or tert-butyl-substituted biphenyl; The R1 is represented by one of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyridyl, quinolyl, furyl, thienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, and tert-butyl-substituted biphenyl.

5. The compound of the general formula according to claim 1 or 2, characterized in that The Z9, Z 10 are CR, and R is hydrogen, said Z1-Z8 are CR, and the definition of R is the same as that in claim 1; Alternatively, Z2 and Z7 are both CR, and R is tert-butyl, and Z1, Z3-Z6, Z8-Z 10 are CR, and the R is hydrogen.

6. A compound of the general formula selected from the following specific structural compounds:

7. Use of the compound according to any one of claims 1 to 6 as a light-emitting layer material or a light-emitting dye in an organic electroluminescent device.

8. An organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, characterized in that: The organic layer comprises at least one compound according to any one of claims 1 to 6.

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