WO2023093829A1

WO2023093829A1 - Compound, light-emitting device, and display apparatus

Info

Publication number: WO2023093829A1
Application number: PCT/CN2022/134232
Authority: WO
Inventors: 徐增; 李崇; 曹旭东; 张翰
Original assignee: 华为技术有限公司; 江苏三月科技股份有限公司
Priority date: 2021-11-25
Filing date: 2022-11-25
Publication date: 2023-06-01
Also published as: CN116178403A

Abstract

The present application relates to the field of photoelectricity, and provides a compound, a light-emitting device, and a display apparatus. The compound is a boron-containing compound and has a structure as shown in formula (I). The compound can be used for improving the luminous color purity of a green light-emitting device.

Description

Compound and light-emitting device, display device

Cross References to Related Applications

This application claims the priority of a Chinese patent application with application number 202111413883.5 and application title "Compounds and Light-Emitting Devices, Display Devices" filed with the China Patent Office on November 25, 2021, the entire contents of which are incorporated by reference in this application .

technical field

The present application relates to the field of optoelectronics, in particular to a compound, a light-emitting device, and a display device.

Background technique

With the advent of the information age, the display standards of the new generation of ultra-high definition (UHD) video production and display systems put forward higher requirements for display technology. In addition to high efficiency and stability, luminescent materials also need narrower half-peak width to improve the purity of the device's luminescent color. In the full-color light-emitting device of organic light-emitting diode (OLED)-red green blue (RGB) three primary colors, green is used as the main light-emitting color, providing 60% brightness of the full screen, so the development of green light-emitting devices The study of organic materials for the light-emitting layer occupies an important position in the field of OLEDs. At present, the field of green light devices mainly focuses on phosphorescent materials and thermally activated delayed fluorescence (TADF) materials. The triplet state emits light and achieves 100% internal quantum efficiency. However, display devices made of phosphorescence and TADF materials all have the problem of poor color purity and cannot meet the requirements of future display standards.

Contents of the invention

The application provides a compound, a light-emitting device, and a display device. Specifically, the compound is a boron-containing compound, so as to improve the luminous color purity of the green device.

In the first aspect, a compound is provided, which has the structure shown in formula (I),

Wherein, each Z is independently represented as -C(R ₁ ), the R _1s in each Z are the same or different, and adjacent R _1s can be connected to form a ring; the R _1s in each Z are each independently selected from hydrogen, deuterium , tritium, halogen, substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C3~C10 cycloalkyl, substituted or unsubstituted C1~C10 alkoxy, substituted or unsubstituted C1~C10 aryloxy substituted or unsubstituted arylamino group, substituted or unsubstituted C6~C30 aryl group, substituted or unsubstituted C2~C30 heteroaryl group or C1-C18 electron-withdrawing group, C1-C18 electron-withdrawing group The group contains at least one of O, N, S, B, P and F;

M _is one of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C4-C30 heteroaromatic ring;

X ₁ is selected from one of O, S, Se, N(R ₂ ) or C(R ₃ )(R ₄ );

X ₂ is selected from one of O, S, Se, N(R ₅ ) or C(R ₆ )(R ₇ );

R ₂ and R ₅ are each independently selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2 One of ~C30 heteroaryl groups;

R ₃ , R ₄ , R ₆ , and R ₇ are each independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted Substituted C1~C10 alkoxy, substituted or unsubstituted C1~C10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6~C30 aryl, and substituted or unsubstituted C2~C30 One of the heteroaryl groups, and R ₅ , R ₆ , R ₇ can be connected with M ₁ to form a ring;

Substituents in substituted C1-C10 alkyl groups, substituents in substituted C3-C10 cycloalkyl groups, substituents in substituted C1-C10 alkoxy groups, substituents in substituted C1-C10 aryloxy groups , the substituent in the substituted arylamino group, the substituent in the substituted C6～C30 aryl group and the substituent in the substituted C2～C30 heteroaryl group are each independently selected from halogen, C1～C10 alkyl, C3～ C10 cycloalkyl, C1-C10 alkoxy, C1-C10 aryloxy, arylamino, C6-C30 aryl or C2-C30 heteroaryl.

In the compound of the present application, the fused ring structure formed by the boron atom, X ₁ , X ₂ and M ₁ is connected to a substituted or unsubstituted pyrene ring, and the fused ring skeleton formed is a rigid skeleton structure, which can reduce the structural relaxation degree of the excited state , X ₁ is selected from one of O, S, Se, or N(R ₂ ), X ₂ is selected from one of O, S, Se, or N (R ₅ ), so that the compound can at least contain Two heteroatoms can contribute to the resonance effect, which can make the HOMO energy level and LUMO energy level more evenly distributed on the entire molecule, the resonance area is larger, and the resonance effect is stronger, so that the half-high bandwidth of the luminescence peak is wider. Narrow, and then can achieve a narrower half-width, such as less than 30nm half-width can be achieved. The compound of the present application has a high fluorescence quantum yield while having a narrow half-peak width, and has a suitable highest occupied molecular orbital (highest occupied molecular orbital, HOMO) energy level and the lowest unoccupied molecular orbital (lowest unoccupied molecular orbital, LUMO) energy level, which can be used as the dopant material of the light-emitting layer of the light-emitting device, thereby improving the efficiency of the device and the purity of the light-emitting color.

In a possible implementation, the compound is selected from any of the structures shown in formulas (1-1) to (1-3):

In formula (1-3), X ₃ is selected from one of O, S, Se, N(R ₈ ) or C(R ₉ )(R ₁₀ );

R ₈ is selected from substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl, substituted or unsubstituted C6～C30 aryl and substituted or unsubstituted C2～C30 heteroaryl a kind of

R ₉ and R ₁₀ are each independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkane Oxygen, substituted or unsubstituted C1-C10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl .

Compounds with structures represented by formulas (1-1) to (1-3) have better rigidity, which can further reduce the degree of structural relaxation of the excited state, narrow the half-peak width, and improve the purity of the luminescent color of the device.

In a possible implementation, the compound is selected from any of the structures shown in formulas (1-4) to (1-8):

In (1-7) and the formula (1-8), X ₃ is selected from one of O, S, Se, N(R ₈ ) or C(R ₉ )(R ₁₀ );

_R in each Z is independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl, substituted or unsubstituted C1～C10 One of alkoxy, substituted or unsubstituted C1-C10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl kind.

Compounds with structures represented by formulas (1-4) to (1-8) have better rigidity, which can further reduce the degree of structural relaxation of the excited state, narrow the half-peak width, and improve the purity of the luminescent color of the device.

In a possible implementation, the compound is selected from any of the structures shown in formulas (2-1) to (2-18):

Compounds with structures shown in formulas (2-1) to (2-18) can contain at least two heteroatoms, which can help to generate resonance effects, and can make the HOMO energy level and LUMO energy level more evenly distributed throughout the molecule , the larger the resonance area, the stronger the resonance effect.

In a possible implementation, the compound is selected from any of the structures shown in formulas (3-1) to (3-23):

Compounds with structures represented by formulas (3-1) to (3-24) contain at least three heteroatoms, so that the light-emitting device can achieve the effects of adjustable spectrum and extended life.

In a possible implementation, the compound is selected from any of the structures shown in formulas (4-1) to (4-6):

Compounds with structures represented by formulas (4-1) to (4-6) contain at least three heteroatoms, so that the light-emitting device can achieve the effects of adjustable spectrum and extended life.

In a possible implementation, the compound is selected from any of the structures shown in formulas (5-1) to (5-24):

Compounds with structures represented by formulas (5-1) to (5-24) contain at least three heteroatoms, so that the light-emitting device can achieve the effects of adjustable spectrum and extended life.

In a possible implementation, the compound has a structure as shown in formula (6-1):

_R in each Z is independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl, substituted or unsubstituted C1～C10 Alkoxy, substituted or unsubstituted C1~C10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6~C30 aryl, and substituted or unsubstituted C2~C30 heteroaryl A sort of.

The compound with the structure shown in formula (6-1) contains two N atoms and one B atom, has a stable structure and simple synthesis, and is helpful for obtaining a long-life luminescent material.

In a possible implementation, the compound is selected from any of the structures shown in formulas (7-1) to (7-10):

X ₃ in formula (7-2) and formula (7-3) are each independently selected from O, S, Se, N(R ₈ ) or C(R ₉ )(R ₁₀ );

R ₈ is selected from substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl, substituted or unsubstituted C6～C30 aryl, and substituted or unsubstituted C2～C30 heteroaryl one of

R ₉ and R ₁₀ are each independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkane Oxygen, substituted or unsubstituted C1~C10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6~C30 aryl, and substituted or unsubstituted C2~C30 heteroaryl kind;

In a possible implementation, the compound is selected from any of the structures shown in formulas (1) to (224):

By introducing different substituents on the condensed ring unit of the compound, the adjustment of the emission position and half-peak width can be further realized, so that the emission position is located in the green light region.

In the second aspect, the present application provides a light-emitting device, which includes a cathode layer, an anode layer, and a functional layer, the functional layer is located between the cathode layer and the anode layer, and the functional layer includes the first aspect of the application and its possible implementation. compound of.

Wherein, the functional layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer stacked in sequence, and the hole transport layer is arranged between the anode layer and the electron injection layer. On the side, the electron injection layer can be disposed on the cathode layer. Besides, the light emitting device may further include a transparent substrate layer, and the anode layer may be connected to the transparent substrate layer.

Since the functional layer of the light-emitting device includes the compound according to the first aspect of the application, the light-emitting device of the present application has the advantages of good luminous color purity and high luminous efficiency.

In a possible implementation manner, the functional layer includes a light-emitting layer, and the dopant material of the light-emitting layer includes the compound according to the first aspect of the present application.

In a possible implementation manner, the light emitting layer includes a first host material, a second host material and a dopant material, and at least one of the first host material and the second host material includes a TADF material.

In a third aspect, a display device is provided, and the display device includes the light emitting device of the second aspect of the present application.

Among them, the above-mentioned display devices include, but are not limited to, fields such as smart phones and tablet computers, fields of smart wearable devices, fields of large-size applications such as TVs, fields of VR and microdisplays, and car central control screens or car taillights.

Description of drawings

Fig. 1 is the mass spectrometry test figure of compound 1 of the present application;

Fig. 2 is the NMR test spectrum of compound 1 of the present application;

Fig. 3 is the spectrum test pattern of compound 1 of the present application in toluene solution (10 μ M concentration);

Fig. 4 is the mass spectrometry test figure of compound 86 of the present application;

Fig. 5 is the NMR test spectrum of compound 86 of the present application;

Fig. 6 is the spectral test spectrum of compound 86 of the present application in toluene solution (10 μ M concentration);

Fig. 7 is the mass spectrometry chart of compound 185 of the present application;

Fig. 8 is the NMR test spectrum of compound 185 of the present application;

Fig. 9 is the spectral test pattern of compound 185 of the present application in toluene solution (10 μ M concentration);

FIG. 10 is a schematic structural diagram of an OLED device provided by an embodiment of the present application.

Reference signs:

1-transparent substrate layer; 2-anode layer; 3-hole injection layer; 4-hole transport layer; 5-electron blocking layer; 6-light-emitting layer; 7-hole blocking layer; 8-electron transport layer; 9 - electron injection layer; 10 - cathode layer.

Detailed ways

Hereinafter, the terms used in the specific implementation manners of the present application are firstly explained.

Triplet (T1) state: In a multi-electron molecule or atom, among all paired electrons, the spins of a pair of paired electrons are parallel. At this time, the net spin of the electron is 1; in the magnetic field, due to the three different orientations (parallel, perpendicular and antiparallel) of its spin relative to the direction of the magnetic field, it splits into three states of different energy levels.

Singlet excited (singlet, S1) state: In a multi-electron molecule or atom, the spins (1/2) of all paired electrons are in an antiparallel state. At this time, the net spin of the electron is zero; in a magnetic field , the state in which the energy level does not split.

TADF: When the energy of the triplet excited state (T1 state) is close to that of the singlet excited state (S1 state), molecules in the triplet excited state can reach the singlet excited state through the reverse intersystem crossing (RISC) process, Then return to the ground state through a radiative transition process. This series of processes is called E-type delayed fluorescence, also known as thermally activated delayed fluorescence, or TADF for short.

The light emitting devices may include red light devices, blue light devices and green light devices. Compared with red light devices and blue light devices, the research on green light devices is relatively late, and with the development of OLED-RGB three primary color light emitting devices, the role of green light devices has become particularly important. As for green light devices, phosphorescent doped materials are currently commercially used, but it is difficult to narrow the luminous peak shape by simple methods, resulting in a wide half-peak width and low luminous color purity. In order to meet higher color rendering standards, it is of great significance to study high-efficiency green fluorescent doped materials with narrow half-peak widths, such as TADF materials.

In order to obtain a TADF material with a narrow half-width to improve the luminous color purity of a light-emitting device, the present application provides a compound, which has a structure as shown in formula (I),

The synthetic method of compound shown in formula (I) comprises:

With the compound shown in formula A as raw material A, with the compound shown in formula B as raw material B, with the raw material C of the compound shown in formula C,

The raw material A is coupled with the raw material B and the raw material C respectively, and the compound represented by the formula (I) is obtained after a cyclization reaction.

As a possible implementation, the synthetic reaction route of the compound represented by formula (I) is as follows:

Specifically, in a possible implementation, the synthesis of the compound represented by formula (I) includes the following steps:

With raw material A (a bromo-iodine compound containing pyrene as shown in formula A), raw material B (a substituent containing active hydrogen as shown in formula B), raw material C (a benzene containing active hydrogen shown in formula C) Boronic acid) is the starting material, wherein, the compound based on the general formula of raw material A, raw material B and raw material C can be obtained through commercialization, and the coupling of raw material A and raw material B through Pd catalysis or Ullmann (Ullmann) coupling The reaction can obtain intermediate B, intermediate B and raw material C can obtain intermediate C through Suzuki coupling reaction, and _intermediate C can react with BBr to finally obtain the target product, namely the compound shown in formula (1).

In a possible implementation, when M in the formula ( ₁ ) is a six-membered ring, the raw material B (substituent containing active hydrogen) can be expressed as raw material B1 (benzene substituent containing active hydrogen), and Raw material A and raw material B1 can obtain intermediate B1 through Pd-catalyzed coupling or Ullmann reaction, intermediate B1 and raw material C can obtain intermediate C1 through Suzuki coupling reaction, and intermediate C1 can react with _BBr3 to finally obtain the target product, namely Compound represented by formula (1-1). Concrete reaction route is as follows:

In a possible implementation, when M in formula ( ₁ ) is a five-membered ring, raw material B (substitute containing active hydrogen) can be represented as raw material B2 or B3 (benzene substituent containing active hydrogen) , intermediate B2 or intermediate B3 can be obtained by Pd-catalyzed coupling or Ullmann reaction of raw material A and raw material B2 or raw material B3, and intermediate C2 or intermediate C2 can be obtained by intermediate B2 or intermediate B3 and raw material C by Suzuki coupling reaction Intermediate C3, intermediate C2 or intermediate C3 react with BBr ₃ to finally obtain the target product, namely the compound represented by formula (1-2) or formula (1-3). Concrete reaction route is as follows:

It can be understood that, in the above-mentioned reaction, the acquisition of the compound shown in the target product formula (1-1), formula (1-2) and formula (1-3) can be obtained from commercially available raw material A, raw material B ( Including raw material B1, raw material B2 and raw material B3) and raw material C preparation, and the preparation of intermediate B and intermediate C from raw material A all utilize the same type of chemical reaction, therefore, each compound in this application can refer to the above reaction process Execution, the synthesis process of the specific compound should be understood as within the scope of the above synthesis process, any compound in the embodiment of the present application can be prepared according to the same synthesis method to produce the same type of target product.

The compound having the above structural formula of the present application will be further described in detail in conjunction with specific examples below.

The synthesis of embodiment 1 compound 1

Molecular structure of compound 1:

The synthetic route of compound 1 is as follows:

Wherein, Pd ₂ (dba) ₃ is tris(dibenzylideneacetone)dipalladium, and S-phos is 2-bicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl.

The specific preparation steps of compound 1 are as follows:

1) Synthesis of intermediate M-1: Add raw material 1 into a flask, add raw material 2, K ₂ CO ₃ , S-phos, Pd ₂ (dba) ₃ , toluene in sequence, then replace nitrogen, heat and stir. Cool down to room temperature after the reaction, add saturated brine, extract with ethyl acetate three times, dry the organic phase with anhydrous sodium sulfate, concentrate the organic phase and separate by column chromatography to obtain intermediate M-1.

Mass spectrometer test: [M ⁺ H] ⁺ Found 614.31, Theoretical: 613.23.

2) Put the intermediate M-1 into the flask, add raw material 3, K ₂ CO ₃ , Pd(PPh ₃ ) ₄ , THF, water in sequence, and then replace nitrogen, heat and stir. Cool down to room temperature after the reaction, add saturated brine, extract with ethyl acetate three times, dry the organic phase with anhydrous sodium sulfate, concentrate the organic phase and separate by column chromatography to obtain intermediate M-2.

Mass spectrometer test: [M ⁺ H] ⁺ measured value: 813.64, theoretical value: 812.51.

3) Add the intermediate M-2 into the bottle, add m-dichlorobenzene, protect with nitrogen, then add BBr ₃ , heat and stir, then directly spin dry, and separate by silica gel column chromatography to obtain compound 1.

Mass spectrometer test: The specific mass spectrometry test chart can be found in Figure 1, as shown in Figure 1, [M ⁺ H] ⁺ measured value: 821.72, theoretical value: 820.49, the measured value is basically consistent with the theoretical value, indicating that compound 1 can be obtained.

Compound 1 NMR characterization data:

Figure 2 is the NMR test spectrum of Compound 1 of the present application. In conjunction with Figure 2, the NMR standard data of Compound 1 is as follows:

1H NMR (400MHz, Chloroform-d): δ (ppm) = 9.05-9.03 (d, 1H), 8.99-8.98 (d, 1H), 8.89-8.88 (d, 1H), 8.55 (d, 1H), 8.53 -8.51(d,1H),8.31-8.20(m,7H),8.01-7.98(d,1H),7.59-7.56(m,1H),7.54-7.52(d,1H),7.46-7.43(m, 1H), 1.66(s,9H), 1.65(d,18H), 1.57(s,9H), 1.53(s,9H).

Figure 3 is the half-width test spectrum of Compound 1 of the present application. As shown in 3, Compound 1 has a narrower half-width, which is less than 30nm.

Among them, the synthesis process of the compound of the embodiment of the present application is simple, and the synthesis of the compound can be realized without the use of dangerous chemicals such as butyllithium. At the same time, the raw materials used have high asymmetry, large dipole moment, good solubility, and good processing performance. good.

Among them, it can be understood that the hydrogen and alkyl-C(CH ₃ ) ₃ in compound 1 can be replaced by other groups, such as alkyl, cycloalkyl or epoxy groups with other carbon numbers, corresponding All the above compounds should be understood as being within the protection scope of the present application.

Example 2

Synthesis of Compound 86

The preparation of intermediate 2-1 refers to the preparation of Example 1. LC-MS: found: 508.28 ([M+H]+), theoretical: 507.16.

The preparation of intermediate 2-2 refers to the synthesis of compound 1.

The preparation of compound 86: Add intermediate 2-2 to the bottle, add o-dichlorobenzene, nitrogen protection, then add n-butyllithium, add n-butyllithium, stir for two hours, add BBr3, and then heat up at 160°C Stir at ℃ for 6 h, then spin dry directly, and separate compound-86 by silica gel column chromatography. LC-MS: found: 713.40 ([M+H]+), theoretical: 712.40. Note: When compound 86 was synthesized, two hydrogens were removed to form a cyclohexene structure. Structural characterization maps are shown in Figure 4 and Figure 5.

Compound 86 NMR characterization data: 1H NMR (400MHz, Chloroform-d): δ (ppm) = 9.02-8.99 (d, 1H), 8.87 (s, 1H), 8.74-8.72 (d, 1H), 8.60-8.57 ( d,1H),8.3(s,1H),8.25-8.16(m,5H),7.99-7.93(m,2H),7.62-7.58(m,2H),3.49-3.44(m,1H),3.17- 3.12 (m, 1H), 2.96-2.90 (m, 1H), 2.34-2.29 (m, 1H), 2.12-1.78 (m, 4H), 1.64-1.62 (m, 18H). 1.552 (s, 9H).

Figure 6 is the half-width test pattern of compound 1 of the present application. As shown in 6, compound 86 has a narrower half-width, which is less than 30nm.

Example 3

Synthesis of compound 185

The preparation of intermediate 3-1 refers to the preparation of Example 1.

The preparation of compound 185 refers to the preparation of Example 2. LC-MS: found: 659.32 ([M+H]+), theoretical: 658.35. Structural characterization diagrams are shown in Figure 7 and Figure 8.

Compound 185 NMR characterization data:

1H NMR (400MHz, Chloroform-d): δ (ppm) = 9.11-9.08 (d, 1H), 8.77-8.75 (d, 1H), 7.71 (s, 1H), 8.55 (s, 1H), 8.50-8.48 (d,1H),8.28-8.23(m,4H),8.18-8.15(d,1H),8.02-8.00(d,1H),7.88-7.86(d,1H),7.62-7.57(m,1H) ,7.50-7.48(d,1H),7.42-7.39(m,1H),7.17-7.16(d,1H),1.69(s,9H),1.65(s,9H),1.51(s,9H).

Figure 9 is the half-width test pattern of compound 1 of the present application. As shown in 9, compound 185 has a narrow half-width, which is less than 30nm.

Compound performance test

The physical and chemical properties of compound 1, comparative compound ref-1, and comparative compound ref-2 were tested respectively, and the test results are listed in Table 1.

Wherein, the structures of comparative compound ref-1 and comparative compound ref-2 are as follows:

Among them, the specific test process of each test index is as follows:

HOMO energy level: Tested by the ionization energy test system (IPS-3), the test is a nitrogen environment.

Energy level gap Eg: tested by a double-beam ultraviolet-visible spectrophotometer (model: TU-1901).

LUMO level: It is the sum of the HOMO level and Eg.

Fluorescence quantum efficiency (PLQY) and full width at half maxima (FWHM) were measured by Horiba's Fluorolog-3 series fluorescence spectrometer in the thin film state.

Table 1

From the data in Table 1 above, it can be seen that the compound of the present application has a suitable HOMO energy level, and is doped as a dopant material in the host material, which is beneficial to suppress the generation of carrier traps, improve the energy transfer efficiency of host and guest, and thus improve the luminous efficiency of the device ;Using the compound of the present application as a doping material has a higher fluorescence quantum efficiency; at the same time, the spectral FWHM of the material is narrower, which can effectively improve the color gamut of the device, improve the purity of the luminous color of the device, and improve the luminous efficiency of the device.

The effect of the compounds of the present application in light-emitting devices will be described in detail below in combination with specific device examples and device comparison examples.

Device Embodiment

OLED devices were prepared by using compound 1 of the example of the present application and comparative compounds ref-1 and ref-2, respectively. Among them, the structures of the compounds used in the preparation of the OELD device and the comparative compounds are as follows:

Fig. 10 is a schematic structural view of an OLED device of the present application. As shown in Fig. 10, the structure of the OLED device includes a transparent substrate layer 1, an anode layer 2, a hole injection layer 3, a hole transport layer 4, Electron blocking layer 5 , light emitting layer 6 , hole blocking layer 7 , electron transport layer 8 , electron injection layer 9 , and cathode layer 10 . Among them, the hole injection layer 3, the hole transport layer 4, the electron blocking layer 5, the light emitting layer 6, the hole blocking layer 7, the electron transport layer 8 and the electron injection layer 9 stacked in sequence can constitute the functional layer of the OLED device. , the compound of the present application can be formed in the light-emitting layer 6 .

The preparation method of the OLED device of the embodiment of the present application is as follows:

10, the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness is 150nm) disposed on the surface of the transparent substrate layer 1 is washed, that is, cleaning agent (Semiclean M-L20) is washed successively, Washing with pure water, drying, and then performing ultraviolet-ozone washing to remove organic residues on the surface of the ITO anode layer 2 . On the ITO anode layer 2 after the above-mentioned washing, utilize a vacuum vapor deposition device, vapor deposition film thickness is 10nm HT-1 and HI-1 as hole injection layer 3, the mass ratio of HT-1 and HI-1 is 97:3. Next, HT-1 was evaporated to a thickness of 60 nm as the hole transport layer 4 . Subsequently, EB-1 was evaporated to a thickness of 30 nm as the electron blocking layer 5 . After the evaporation of the above-mentioned electron blocking material is completed, the light-emitting layer 6 of the OLED light-emitting device is fabricated, using Host-1 and Host-2 as dual host materials, Ir(ppy)3 as a phosphorescent dopant material, and compound 1 as a fluorescent dopant material, The film thickness of the light-emitting layer was 40 nm. After the above-mentioned light-emitting layer 6, continue to vacuum-deposit HB-1 with a film thickness of 5 nm, and this layer is the hole blocking layer 7 . After the above-mentioned hole blocking layer 7, vacuum evaporation of ET-1 and Liq was continued, the mass ratio of ET-1 and Liq was 1:1, and the film thickness was 30 nm. This layer was the electron transport layer 8 . On the electron transport layer 8, a LiF layer with a film thickness of 1 nm was formed by a vacuum evaporation device, and this layer was the electron injection layer 9. On the electron injection layer 9 , a Mg:Ag electrode layer with a film thickness of 80 nm was produced by a vacuum evaporation device, and the mass ratio of Mg and Ag was 1:9. This layer was used for the cathode layer 10 .

Device comparison examples were prepared by replacing compound 1 in the above steps with compound ref-1 and compound ref-2, respectively.

The performance parameters of the device embodiment and the device comparison example were tested respectively, and the test results are listed in Table 2. Among them, the specific test process of each test index is as follows: voltage, external quantum efficiency, and luminous peak use IVL (current-voltage-brightness) test system (Suzhou Fushida Scientific Instrument Co., Ltd.); life test system is Japan System Technology Research Co., Ltd. EAS-62C OLED device life tester; LT95 refers to the time taken for the brightness of the device to decay to 95%, and LT90 refers to the time used for the brightness of the device to decay to 90%; voltage, external quantum efficiency, and luminous peak are all at 1000cd/m ² Next test.

Table 2

As can be seen from the test data in Table 2, compared with device comparative example 2, the device embodiment 1 of the compound of the present application, the voltage of the OLED device is significantly lower than that of device comparative example 2, and the device life is compared with that of known materials. OLED devices have been greatly improved.

Proved by the above experiments, the compound of the present application has the following advantages:

(1) The compound of the present application is applied to OLED devices, and can be used as a dopant material for the light-emitting layer material, which can emit green fluorescence under the action of an electric field, and can be applied to the fields of OLED lighting or OLED display;

(2) The compound of the present application has a higher fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the sensitized material is close to 100%;

(3) The compound of the present application is used as a doping material, and the introduction of a material with an exciton-sensitizing function can effectively improve the luminous efficiency of a light-emitting device;

(4) The spectrum FWHM of the compound of the present application is relatively narrow, and can be less than or equal to 30nm, which can effectively improve the luminous color purity of the light-emitting device and improve the luminous efficiency of the light-emitting device;

(5) The compound of the present application has a suitable energy level, which can effectively improve the stability of the light-emitting device.

The above is only the specific implementation of the application, but the scope of protection of the application is not limited thereto. Anyone familiar with the technical field can easily think of changes or replacements within the technical scope disclosed in the application, and should cover Within the protection scope of this application. Therefore, the protection scope of the present application should be based on the protection scope of the claims.

Claims

A compound, characterized in that the compound has a structure as shown in formula (I),

Wherein, each of the Zs is independently represented as -C(R 1 ), the R 1s in each of the Zs are the same or different, the adjacent R 1s can be connected to form a ring, and the R 1s in each of the Zs are R1 are each independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl, substituted or unsubstituted C1～C10 alkoxy, Substituted or unsubstituted C1~C10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C2~C30 heteroaryl or C1-C18 electron-withdrawing group, the C1-C18 electron-withdrawing group contains at least one of O, N, S, B, P and F;

The M1 is one of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C4-C30 heteroaromatic ring;

The X 1 is selected from one of O, S, Se, N(R 2 ) or C(R 3 )(R 4 );

The X 2 is selected from one of O, S, Se, N(R 5 ) or C(R 6 )(R 7 );

R 2 and R 5 are each independently selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2 One of ~C30 heteroaryl groups;

R 3 , R 4 , R 6 , and R 7 are each independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted Substituted C1~C10 alkoxy, substituted or unsubstituted C1~C10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6~C30 aryl, and substituted or unsubstituted C2~C30 One of the heteroaryl groups, and R 5 , R 6 , R 7 can be connected with M 1 to form a ring;

The substituted C1-C10 alkyl group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 alkoxy group, the substituted C1-C10 aryloxy group, the substituted arylamino group , the substituents in the substituted C6-C30 aryl and the substituted C2-C30 heteroaryl are each independently selected from halogen, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy group, C1~C10 aryloxy group, arylamino group, C6~C30 aryl group or C2~C30 heteroaryl group.
The compound according to claim 1, wherein the compound is selected from any of the structures shown in formulas (1-1) to (1-3):

In the formula (1-3), the X 3 is selected from one of O, S, Se, N(R 8 ) or C(R 9 )(R 10 );

R 8 is selected from substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl, substituted or unsubstituted C6～C30 aryl and substituted or unsubstituted C2～C30 heteroaryl a kind of

R 9 and R 10 are each independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkane Oxygen, substituted or unsubstituted C1-C10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl .
The compound according to claim 1, wherein the compound is selected from any of the structures shown in formulas (1-4) to (1-8):

The X 3 in the formula (1-7) and the formula (1-8) are each independently selected from O, S, Se, N(R 8 ) or C(R 9 )(R 10 ) one of

R in each said Z is each independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl, substituted or unsubstituted C1 ~C10 alkoxy, substituted or unsubstituted C1~C10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6~C30 aryl and substituted or unsubstituted C2~C30 heteroaryl kind of.
The compound according to claim 1, wherein the compound is selected from any of the structures shown in formulas (2-1) to (2-18):
The compound according to claim 1, wherein the compound is selected from any of the structures shown in formulas (3-1) to (3-23):
The compound according to claim 1, wherein the compound is selected from any of the structures shown in formulas (4-1) to (4-6):
The compound according to claim 1, wherein the compound is selected from any of the structures shown in formulas (5-1) to (5-24):

R in each said Z is each independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl, substituted or unsubstituted C1 ~C10 alkoxy, substituted or unsubstituted C1~C10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6~C30 aryl and substituted or unsubstituted C2~C30 heteroaryl kind of.
The compound according to claim 1, wherein the compound is a structure shown in formula (6-1):

R in each said Z is each independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl, substituted or unsubstituted C1 ~C10 alkoxy, substituted or unsubstituted C1~C10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6~C30 aryl and substituted or unsubstituted C2~C30 heteroaryl kind of.
The compound according to claim 1, wherein the compound is selected from any of the structures shown in formulas (7-1) to (7-10):

The X 3 in the formula (7-2) and the formula (7-3) are each independently selected from O, S, Se, N(R 8 ) or C(R 9 )(R 10 );

The R is selected from substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl, substituted or unsubstituted C6～C30 aryl and substituted or unsubstituted C2～C30 heteroaryl one of the bases;

The R 9 and the R 10 are each independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1～C10 alkoxy, substituted or unsubstituted C1～C10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6～C30 aryl and substituted or unsubstituted C2～C30 heteroaryl one of

R in each said Z is each independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl, substituted or unsubstituted C1 ~C10 alkoxy, substituted or unsubstituted C1~C10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6~C30 aryl and substituted or unsubstituted C2~C30 heteroaryl kind of.
The compound according to claim 1, wherein the compound is selected from any of the structures shown in formulas (1) to (224):
A light-emitting device, characterized in that it comprises a cathode layer, an anode layer and a functional layer, the functional layer is located between the cathode layer and the anode layer, and the functional layer comprises any one of claims 1-10 said compound.
The light-emitting device according to claim 11, wherein the functional layer comprises a light-emitting layer, and a dopant material of the light-emitting layer comprises the compound.
The light-emitting device according to claim 12, wherein the light-emitting layer comprises a first host material, a second host material and the dopant material, and the first host material and the second host material At least one includes a thermally excited delayed fluorescent material.
A display device, characterized by comprising the light emitting device according to any one of claims 11-13.