7-phenylquinolone derivatives, methods of preparation, and organic electroluminescent devices

Abstract

The application belongs to the technical field of organic light-emitting materials and semiconductor, and particularly relates to a 7-phenyl quinolone derivative, a preparation method and an organic electroluminescent device. After the 7-phenyl quinolone derivative is applied to a light-emitting layer of the organic electroluminescent device as a host light-emitting material or a guest light-emitting material, the luminous efficiency and the service life of the organic electroluminescent device are effectively improved, a smaller efficiency roll-off is obtained, the 7-phenyl quinolone derivative has a high glass transition temperature, and therefore the stability and the yield of the organic electroluminescent device are effectively improved. In addition, the synthesis path of the 7-phenyl quinolone derivative is relatively simple, which is helpful to the structure optimization of the 7-phenyl quinolone derivative and the reduction of production cost.

Description

Technical Field

[0001] This invention belongs to the field of organic light-emitting materials and semiconductor technology, specifically relating to 7-phenylquinolone derivatives and their preparation methods and organic electroluminescent devices. Background Technology

[0002] With the widespread use of electronic devices, people's demands for display technology are constantly increasing, such as higher resolution, contrast ratio, wider color gamut, and faster response speed. Traditional liquid crystal display technology is gradually becoming unable to meet these demands in some aspects, and organic light-emitting diode (OLED) technology has become a research hotspot due to its advantages of self-illumination, wide viewing angle, and fast response.

[0003] A typical organic light-emitting diode (OLED) device structure includes an anode, a hole transport layer, an emissive layer, an electron transport layer, and a cathode. When a voltage is applied between the anode and cathode, holes are injected from the anode and then move towards the emissive layer via the hole transport layer; simultaneously, electrons are injected from the cathode and move towards the emissive layer via the electron transport layer. In the emissive layer, electrons and holes recombine to form excitons, which transfer energy to the luminescent material, causing the material to emit light.

[0004] The fabrication process of organic electroluminescent devices is highly complex, and significant material loss occurs during the deposition of various functional layer materials, resulting in raw material waste. This waste not only increases production costs but also hinders the large-scale promotion of organic electroluminescence technology. Therefore, finding a host and guest luminescent material that can achieve low-cost, large-scale, and sustainable production while possessing good luminous efficiency is a pressing challenge that needs to be overcome.

[0005] Quinolones are an important class of synthetic antibacterial drugs, widely used in the pharmaceutical field. Because the synthetic routes of these derivatives are relatively simple and they are easily chemically modified, they hold promise for application in the field of organic electroluminescent materials. Patent CN115636819A discloses the general formula (9). The quinolone compounds shown can be used as guest light-emitting materials in the light-emitting layer of organic electroluminescent devices. They can effectively reduce the start-up voltage and efficiency roll-off of organic electroluminescent devices, but the lifespan of organic electroluminescent devices has not been significantly improved. Summary of the Invention

[0006] To address the shortcomings of the existing technologies, this invention provides 7-phenylquinolone derivatives, their preparation methods, and organic electroluminescent devices. By using the 7-phenylquinolone derivatives of this invention as the host or guest luminescent material in the luminescent layer of an organic electroluminescent device, the luminous efficiency and lifespan of the organic electroluminescent device can be effectively improved, overcoming the technical defects of quinolone compounds in the prior art.

[0007] This invention is achieved through the following technical solution:

[0008] The first objective of this invention is to provide a 7-phenylquinolone derivative, the structural formula of which is shown in general formula 1: 7-Phenylonone derivatives are formed by Y bonded to the main structure via single bonds. The structural formula of the main structure is as follows: In general formula one, Y and R are each independently selected from substituted or unsubstituted C6~C6. 40 aryl, substituted or unsubstituted C4~C 40 heteroaryl; C4~C 40 In the heteroaryl group, the heteroatom contains at least one of N, O, S and Si, and C4~C 40 The heteroaryl group can be a monocyclic heteroaryl, a polycyclic heteroaryl, or a fused-ring heteroaryl.

[0009] Preferred, substituted or unsubstituted C6~C 40 In the aryl group, the substituent is selected from phenyl, biphenyl, naphthyl, phenanthryl or C1~C6 alkyl; substituted or unsubstituted C4~C 40 In heteroaryl compounds, the substituents are selected from C1 to C2. 12 Alkyl, cyano, trifluoromethyl, F atom, D atom, deuterated methyl, deuterated tert-butyl, deuterated phenyl, N,N-dimethylallyl, N-methylcyclohexenyl, phenyl, naphthyl, biphenyl, benzyl, 9,10-benzophenanthryl, dibenzofuranyl, dibenzothiopheneyl, 9-benzylfluorenyl, carbazoleyl or deuterated carbazoleyl.

[0010] Preferably, R is any one of the following groups r1 to r177, and the structural formulas of r1 to r177 are as follows: , , , , , , , , , , , , ,

[0011] , , , , , , , , , .

[0012] * indicates the location where R is bonded to the main structure. Among them, r10, r11, r16, r17, r19~r28, r33, r34, r37, r39~r41, r45~r47, r56~r64, r67~r69, r136, r141, r144~r149, r151~r159, r165, r167, and r173 are all bonded to the main structure through only one *.

[0013] Preferably, Y is selected from any one of y1 to y107, and the structural formulas of y1 to y107 are as follows:

[0014] ,

[0015] , , , , , , , , , , , , , ,

[0016] .

[0017] In y107, L1 and L2 are independently selected from H and C1~C, respectively. 10 Alkyl groups, C3~C 10 The cycloalkyl, phenyl, naphthyl, biphenyl, phenanthrene, or pyrene group; in addition, * indicates the position where Y is bonded to the main structure, wherein y1~y7, y9, y11, y12, y17, y18, y21, y22, y35, y61, y68, y94, y95, y105, and y106 are all bonded to the main structure through only one *.

[0018] Preferably, the 7-phenylquinolone derivative is any one of compound 1 to compound 420, and the structural formulas of compounds 1 to 420 are as follows:

[0019] , , , , , , , , , , , , , , , , , , , , , , , , , , , 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、

[0020] 、 、

[0021] 、 、

[0022] 、 、

[0023] 、 、

[0024] 、 、

[0025] 、 、

[0026] 、 、

[0027] 、 、

[0028] 、 ,

[0029] , , , ,

[0030] , , , ,

[0031] , ,

[0032] , , , ,

[0033] , , , , , ,

[0034] , ,

[0035] , .

[0036] The second objective of this invention is to provide a method for preparing 7-phenylquinolone derivatives, wherein when Y is y107, the method includes the following steps:

[0037] The synthetic route for 7-phenylquinolone derivatives is shown in the reaction formula:

[0038] .

[0039] Using 4-biphenylacetone and N,N-dimethylformamide dimethyl acetal as raw materials, nucleophilic addition was performed, followed by protonation transfer and intramolecular dehydration to obtain intermediate Mn-1.

[0040] Intermediate Mn-1 was mixed with 3-phenyl-1,4,2-dioxazol-5-one, and then cyclized under the action of a metal catalyst to obtain intermediate Mn-2.

[0041] Interaction between intermediate Mn-2 and diaryltrifluoromethanesulfonic acid iodide compounds: the central iodine atom of the diaryltrifluoromethanesulfonic acid iodide compounds is in a high valence state and has strong electrophilicity. At the same time, intermediate Mn-2 is deprotonated under alkaline conditions to generate a strongly nucleophilic amino anion. The two undergo a nucleophilic substitution reaction to generate intermediate Mn-3.

[0042] Using intermediate Mn-3 and I2 as raw materials, in an alkaline environment, I2 first undergoes an electrophilic substitution reaction with the α-position of the carbonyl group of intermediate Mn-3, and then, through electron transfer and rearrangement processes, intermediate Mn is obtained.

[0043] Using intermediate Mn as a raw material, 7-phenylquinolone derivatives are obtained by reacting reactant A with reactant A under catalysis through nucleophilic substitution reaction or Suzuki reaction.

[0044] Reactant A is selected from R-boron ester, R-boronic acid or R-secondary amine.

[0045] A second objective of this invention is to provide a method for preparing 7-phenylquinolone derivatives, wherein when Y is one of the substituents y1 to y106, the method comprises the following steps:

[0046] The synthetic route for 7-phenylquinolone derivatives is shown in the reaction formula:

[0047] .

[0048] Using 4-biphenylacetone and N,N-dimethylformamide dimethyl acetal as raw materials, nucleophilic addition was performed, followed by protonation transfer and intramolecular dehydration to obtain intermediate Mn-1.

[0049] Intermediate Mn-1 was mixed with 3-phenyl-1,4,2-dioxazol-5-one, and then cyclized under the action of a metal catalyst to obtain intermediate Mn-2.

[0050] Using intermediate Mn-2 and Boc anhydride as raw materials, a nucleophilic substitution reaction was carried out to obtain intermediate Mn-3.

[0051] Using intermediate Mn-3 and I2 as raw materials, under alkaline conditions, I2 undergoes an electrophilic substitution reaction with the α-position of the carbonyl group of intermediate Mn-3 to form an intermediate structure. The intermediate structure then undergoes electron transfer and rearrangement processes to obtain intermediate Mn-4.

[0052] Using intermediate Mn-4 as a starting material, reactant A' is reacted with reactant A' via nucleophilic substitution reaction or suzuki reaction to obtain intermediate Mn-5; reactant A' is selected from R-boron ester, R-boronic acid or R-secondary amine.

[0053] Using intermediate Mn-5 and trifluoroacetic acid as raw materials, Boc was removed to obtain intermediate Mn.

[0054] Using intermediate Mn as a raw material, reactant B under catalysis undergoes a nucleophilic substitution reaction to obtain 7-phenylquinolone derivatives.

[0055] Among them, reactant B is selected from Y'-X, X is selected from Cl, Br or I, and Y' is selected from any one of y1~y106.

[0056] The initial design of this invention was as follows: Y is y107, which serves to give the main structure a three-dimensional configuration, and R is an electron-donating substituent. The whole structure is matched together to be used as a hole-transporting main luminescent material. The test results of organic electroluminescent devices showed that in the embodiments with larger R group volume, the organic electroluminescent devices performed better. Based on this, this invention defines R as substituents of different sizes, and designs Y as a substituent with electron-withdrawing properties. The whole structure constitutes a compound with a DA configuration, that is, a compound with an electron-donating and electron-withdrawing configuration. This type of compound has thermally activated delayed fluorescence properties, and therefore is often used as a guest luminescent material.

[0057] The third objective of this invention is to provide a host luminescent material prepared from the above-mentioned 7-phenylquinolone derivatives, wherein the 7-phenylquinolone derivatives are selected from any one of compounds 1 to 208.

[0058] The fourth objective of this invention is to provide a guest luminescent material prepared from the above-mentioned 7-phenylquinolone derivatives, wherein the 7-phenylquinolone derivatives are selected from any one of compounds 209 to 420.

[0059] The fifth objective of this invention is to provide an organic electroluminescent device, comprising a cathode, an anode, and an organic layer located between the cathode and the anode. The organic layer is composed of 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 sequentially from bottom to top. The hole injection layer is deposited on the anode, the anode is loaded on a substrate, and a capping layer is also disposed on the cathode. The light-emitting layer is made of the aforementioned main light-emitting material.

[0060] The sixth objective of this invention is to provide an organic electroluminescent device, comprising a cathode, an anode, and an organic layer located between the cathode and the anode. The organic layer is composed of 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 sequentially from bottom to top. The hole injection layer is deposited on the anode, the anode is loaded on a substrate, and a capping layer is also disposed on the cathode. The light-emitting layer is made of the aforementioned guest light-emitting material.

[0061] Preferably, organic electroluminescent devices are used in the fields of light emission, image display, or photoelectric signal transmission.

[0062] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0063] 1. Existing quinolone compounds, due to their highly reactive carbonyl groups, readily form hydrogen bonds with adjacent molecules, thereby impairing the lifespan of organic electroluminescent devices; This invention... Perform position labeling to obtain Because a protecting group is attached to the carbonyl group at its ortho position, which is the 3-position of the quinolone, the formation of intermolecular hydrogen bonds can be effectively suppressed. In addition, the N atom on the quinolone provides an n-nonbonding orbital, and the Y substituent connected to the substituent R and the N atom provides a π* antibonding orbital. The n electrons in the n-nonbonding orbital can jump to the π* antibonding orbital, forming a spatial n-π* transition. The spatial n-π* transition increases the reverse intersystem crossing rate and reduces the triplet exciton lifetime, which can effectively suppress the annihilation of triplet excitons to generate high-energy intermediates, reduce chemical bond breaking, and help to significantly improve the lifetime of organic electroluminescent devices.

[0064] 2. This invention uses quinolone as the main skeleton, with simultaneous substitution at the 7- and 3-positions of the quinolone. The 7-position substituent enhances the conjugated system, increasing the electron delocalization range and thus improving luminescence efficiency. The large-volume 3-position substituent reduces intermolecular aggregation and mitigates aggregation quenching effects, further improving the luminescence efficiency of 7-phenylquinolone derivatives in the solid state. The combination of these two factors maintains good luminescence performance in different states. Prior art application number 202211327865.X discloses a luminescent material and its application, as well as an organic electroluminescent device containing it. Studies have shown that compared to the simultaneous substitution at the 3- and 5-positions, or the 2- and 5-positions, or the 5- and 7-positions of quinolone in prior art publications, the electroluminescent device prepared using the 7-phenylquinolone derivative of this invention as the luminescent material has a longer lifetime and higher efficiency. The advantages of the electroluminescent device of the present invention are as follows: In the prior art, the simultaneous substitution of the 5- and 3-positions of quinolones not only leads to aggregation-induced quenching and reduces luminous efficiency, but also makes the compound difficult to synthesize and has poor solubility; In the prior art, the simultaneous substitution of the 2- and 5-positions or the 5- and 7-positions of quinolones causes the carbonyl group to lose the protection of the ortho-substituents, and the entire compound will have a certain degree of photosensitivity, thereby affecting the lifespan of the organic electroluminescent device.

[0065] 3. The synthetic route of the 7-phenylquinolone derivatives of the present invention is relatively simple, and the 7-phenylquinolone derivatives are easy to chemically modify, which facilitates structural optimization and functional design to meet the material performance requirements of different organic electroluminescent devices, accelerate the development of new materials, and reduce production costs. Attached Figure Description

[0066] Figure 1 This is a cross-sectional view of an organic electroluminescent device assembled using the 7-phenylquinolone derivatives of the present invention.

[0067] Figure 2 This is the 1H NMR spectrum of compound 16 from Example 1 of the present invention.

[0068] Figure 3 This is the 1H NMR spectrum of compound 91 from Example 2 of the present invention.

[0069] Figure 4 The image shows the 1H NMR spectrum of compound 37 from Example 3 of this invention.

[0070] Figure 5 This is the 1H NMR spectrum of compound 110 from Example 4 of the present invention.

[0071] Figure 6 The image shows the 1H NMR spectrum of compound 223 from Example 5 of this invention.

[0072] Figure 7 The above is the 1H NMR spectrum of compound 394 from Example 6 of this invention.

[0073] Figure 8 The above is the 1H NMR spectrum of compound 419 from Example 7 of this invention.

[0074] Explanation of reference numerals in the attached figures:

[0075] 1. Substrate, 2. Anode, 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, 11. Capping layer. Detailed Implementation

[0076] The specific embodiments of the present invention are described below with reference to examples. All raw materials and reagents used in the present invention are commercially available. The synthesis process of the 7-phenylquinolone derivatives of compounds 1 to 208 of the present invention is described below:

[0077] In this invention, N,N-dimethylformamide dimethyl acetal refers to DMF-DMA, dichloroethane refers to DCE, and tetrahydrofuran refers to THF.

[0078] Example 1

[0079] The preparation method of compound 16 includes the following steps:

[0080] The reaction equation for the preparation of compound 16 is as follows:

[0081] .

[0082] S1. Under nitrogen protection, a 5L three-necked flask was used to add 196g of 1.0mol of 4-biphenyl ethyl ketone and 2.5L of N,N-dimethylformamide dimethyl acetal. The mixture was stirred and stirred until homogeneous. The temperature was then raised to 102℃ and reacted for 2 hours. After the reaction was completed, the reaction solution was cooled to room temperature and the solvent was concentrated under vacuum to obtain a solid residue. The solid residue was recrystallized from n-heptane to obtain 173g of intermediate M1-1, with a yield of 67%, HPLC purity of 97%, and LC-MS showing a molecular weight of 252.2.

[0083] S2. Under nitrogen protection, take a 5L three-necked flask and add 151g (0.6mol) of intermediate M1-1, 147g (0.9mol) of 3-phenyl-1,4,2-dioxazol-5-one, and 14.3g (0.03mol) of Cp in sequence. *Co(CO)I2, 11.7 g, 0.06 mol AgBF4, and 1.5 L dichloroethane were stirred and mixed thoroughly. The mixture was then heated to 80 °C and reacted for 12 h. After the reaction was completed, the reaction solution was filtered through diatomaceous earth while hot, and the filter cake was repeatedly washed with 1.0 L DCE. The filtrate was concentrated to obtain a solid residue. The solid residue was recrystallized from dichloromethane / n-heptane at a volume ratio of 1:3 to obtain 117 g of intermediate M1-2, with a yield of 88%, HPLC purity of 97%, and LC-MS showing a molecular weight of 222.1.

[0084] S3. Under nitrogen protection, take a 500mL three-necked flask and add 44g, 0.2mol of intermediate M1-2, 86g, 0.2mol of diphenyltrifluoromethanesulfonic acid iodine, 24g, 0.3mol of sodium hydroxide, and 250mL of water in sequence. Seal the flask, stir and mix thoroughly, then heat to 80℃ and react for 6h. After the reaction is completed, cool the reaction solution to room temperature and extract it three times with 1.5L of DCM, each time using 0.5L. Combine the organic phases, dry, filter and concentrate the organic phase to obtain solid residue. The solid residue is purified by silica gel column chromatography with dichloromethane / n-heptane in a volume ratio of 1:3 to obtain intermediate M1-3, weighing 54g, with a yield of 91%, HPLC purity of 98%, and LC-MS showing a molecular weight of 298.1.

[0085] S4. Under nitrogen protection, take a 1.0L three-necked flask and add 44g, 0.15mol of intermediate M1-3, 57g, 0.23mol of iodine, 36g, 0.34mol of sodium carbonate, and 400mL of tetrahydrofuran in sequence. Stir and mix well, and react at room temperature for 6h until the reaction is complete. Concentrate the organic phase and extract it sequentially with 1.0L of dichloromethane and 1.0L of water. The organic phase is dried, filtered, and concentrated to obtain a solid residue. The solid residue is purified by silica gel column chromatography with dichloromethane / n-heptane at a volume ratio of 1:2 to obtain intermediate M1, weighing 76g, with a yield of 90%, HPLC purity of 98%, and LC-MS showing a molecular weight of 424.0.

[0086] S5. Under nitrogen protection, a 100 mL three-necked flask was filled with 4.2 g (0.01 mol) of M1, 2.4 g (0.01 mol) of 9,9-dimethylfluorene-2-boric acid, 40 mL of THF, 10 mL of H2O, and 5.5 g (0.04 mol) of K2CO3. The mixture was stirred and heated to 40 °C. After the solution became clear, 0.23 g (0.2 mmol) of Pd(PPh3)4 was added, and the temperature was raised to 70 °C and the reaction was continued for 12 h until the reaction was complete. The reaction solution was cooled to room temperature and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by silica gel column chromatography with a volume ratio of 1:2 dichloromethane / n-heptane to obtain compound 16, weighing 4.4 g, with a yield of 80%, an HPLC purity of 99%, and a molecular weight of 490.7 as shown by LC-MS.

[0087] The proton NMR data of compound 16 are as follows Figure 2 As shown: 1 H NMR (500 MHz, CD3OD) δ 10.80 (s, 1H),7.96 – 7.81 (m, 3H), 7.80 – 7.68 (m, 3H), 7.57 – 7.20 (m, 12H), 7.05 – 6.92(m, 2H), 1.69 (s, 6H).

[0088] Example 2

[0089] The preparation method of compound 91 includes the following steps:

[0090] The reaction equation for the preparation of compound 91 is as follows:

[0091] .

[0092] S1. Under nitrogen protection, a 500 mL three-necked flask was filled with 44 g and 0.2 mol of intermediate M1-2, 108 g and 0.2 mol of bis(4-tert-butylphenyl)iodotrifluoromethanesulfonate, 24 g and 0.3 mol of sodium hydroxide, and 250 mL of water. The flask was sealed and stirred until homogeneous. The mixture was then heated to 80 °C and reacted for 6 h. After the reaction was completed, the reaction solution was cooled to room temperature, and 1.5 L of DCM was added for extraction in three portions, 0.5 L each time. The organic phases were combined, dried, filtered, and concentrated to obtain a solid residue. The solid residue was purified by silica gel column chromatography with a volume ratio of 1:3 dichloromethane / n-heptane to obtain intermediate M2-3, weighing 64 g, with a yield of 90%, HPLC purity of 98%, and LC-MS showing a molecular weight of 354.2.

[0093] S2. Under nitrogen protection, a 1.0L three-necked flask was used to add 53g and 0.15mol of intermediate M2-3, 57g and 0.23mol of elemental iodine, 36g and 0.34mol of sodium carbonate, and 400mL of THF. The mixture was stirred and stirred until homogeneous, and the reaction was carried out at room temperature for 6 hours until the reaction was complete. The organic phase was concentrated, and 1.0L of dichloromethane and 1.0L of water were added sequentially for extraction. The organic phase was dried, filtered, and concentrated to obtain a solid residue. The solid residue was purified by silica gel column chromatography with a volume ratio of dichloromethane / n-heptane of 1:3 to obtain intermediate M2, weighing 87g, with a yield of 91%, HPLC purity of 98%, and LC-MS showing a molecular weight of 480.1.

[0094] S3. Under nitrogen protection, a 100 mL three-necked flask was filled with 4.8 g of 0.01 mol M2, 1.8 g of 0.01 mol deuterated carbazole, and 50 mL of toluene. The mixture was stirred until the solution was clear. Then, 0.18 g of 0.2 mmol Pd2(dba)3, 0.13 g of 0.5 mmol Am-phos, and 3.8 g of 0.04 mol sodium tert-butoxide were added. The mixture was then heated to 110 °C and reacted for 10 h. After the reaction was complete, the mixture was filtered hot using diatomaceous earth. The filtrate was cooled to room temperature and washed with purified water. The organic phase was separated and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, dried over anhydrous magnesium sulfate, concentrated, and purified by silica gel column chromatography with a 1:3 volume ratio of dichloromethane / n-heptane to obtain compound 91, weighing 4.0 g, with a yield of 76%, an HPLC purity of 99%, and a molecular weight of 527.3 as shown by LC-MS.

[0095] The proton NMR data of compound 91 are as follows Figure 3 As shown: 1 H NMR (500 MHz, CD3OD) δ 11.14 (s, 1H),7.97 – 7.85 (m, 1H), 7.81 – 7.66 (m, 2H), 7.58 – 7.33 (m, 5H), 7.10 (s, 4H), 1.33 (s, 9H).

[0096] Example 3

[0097] The preparation method of compound 37 includes the following steps:

[0098] The procedure was the same as in step S5 of Example 1, except that 4.2 g, 0.01 mol of M1 was replaced with 4.8 g, 0.01 mol of M2, and 2.4 g, 0.01 mol of 9,9-dimethylfluorene-2-boronic acid was replaced with 2.6 g, 0.01 mol of benzothiophene-3-boronic acid pinacol ester, yielding compound 37, weighing 3.7 g, with a yield of 77%, HPLC purity of 99%, and LC-MS showing a molecular weight of 486.2.

[0099] The reaction equation for the preparation of compound 37 is as follows:

[0100] .

[0101] The proton NMR data of compound 37 are as follows Figure 4 As shown: 1 H NMR (500 MHz, CD3OD) δ 10.92 (s, 1H), 8.27 (s, 1H), 7.94 – 7.71 (m, 5H), 7.53 – 7.26 (m, 7H), 7.10 (s, 4H), 1.33 (s, 9H).

[0102] Example 4

[0103] The preparation method of compound 110 includes the following steps:

[0104] The reaction equation for the preparation of compound 110 is as follows:

[0105] .

[0106] The procedure was the same as in step S5 of Example 1, except that 4.2 g, 0.01 mol of M1 was replaced with 4.8 g, 0.01 mol of M2, and 2.4 g, 0.01 mol of 9,9-dimethylfluorene-2-boronic acid was replaced with 3.03 g, 0.01 mol of (10-phenyl-10H-phenoxazine-3-yl)boronic acid, to obtain compound 110, weighing 4.8 g, with a yield of 78%, HPLC purity of 99%, and LC-MS showing a molecular weight of 611.3.

[0107] The proton NMR data of compound 110 are as follows Figure 5 As shown: 1H NMR (500 MHz, CD3OD) δ 10.84 (s, 1H),8.02 – 7.87 (m, 1H), 7.82 – 7.64 (m, 2H), 7.59 – 7.34 (m, 5H), 7.29 – 7.19(m, 2H), 7.17 – 7.05 (m, 8H), 7.04 – 6.89 (m, 5H), 6.84 (d, J = 2.9 Hz, 1H), 1.33 (s, 9H).

[0108] Compounds 1 through 208 were synthesized according to the examples described above.

[0109] Compounds 1 to 208, based on the aforementioned 7-phenylquinolone derivatives, are used as the main luminescent materials in organic electroluminescent devices. The basic structure and fabrication method of the organic electroluminescent devices employ currently recognized industry-standard fabrication techniques. A schematic diagram of the organic electroluminescent device structure is shown below. Figure 1 As shown, the preparation process is described in detail below:

[0110] Under high vacuum conditions, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10 are sequentially deposited on a substrate 1 to obtain a test device. Then, a cover layer 11 is deposited on the cathode 10 of the test device, and then it is encapsulated to complete the fabrication of the test device.

[0111] The experimental setup consists of five main components: anode 2, hole transport layer 4, luminescent layer 6, electron transport layer 8, and cathode 10. Any one or any combination of two 7-phenylquinolone derivatives is used in the luminescent layer 6 region as the primary luminescent material for evaluation. A brief description of the device fabrication process is as follows:

[0112] The substrate 1 is made of glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. In this test, ITO conductive glass was used. Furthermore, the substrate 1 used for displays can also contain a positive array of thin-film transistors and specific display images formed by the combination of these positive arrays.

[0113] The organic layer includes a hole transport layer 4, a light-emitting layer 6, and an electron transport layer 8. The hole transport layer 4 is located between the anode 2 and the light-emitting layer 6, and the electron transport layer 8 is located between the cathode 10 and the light-emitting layer 6. The light-emitting layer 6 is composed of a host light-emitting material and a guest light-emitting material. The host light-emitting material is any one or any combination of two of compounds 1 to 208 of this invention, and the guest light-emitting material is a high-performance... , , One of the materials, wherein the mass ratio of the main luminescent material to the guest luminescent material is 90:10 to 99:1.

[0114] Anode 2 is used to facilitate the injection of holes into the organic layer. It is preferably made of a material with a high work function. Anodes that can be used in this invention include indium tin oxide, indium zinc oxide, tin dioxide, or zinc oxide.

[0115] The cathode 10 is designed to facilitate the injection of electrons into the organic layer. It is preferably made of a material with a low work function, including metals, alloys, or organic combinations thereof. Cathodes applicable to this invention include magnesium, silver, aluminum, aluminum-lithium, calcium, magnesium-indium, or magnesium-silver.

[0116] The functional organic layer is formed by vacuum thermal evaporation, spin coating or printing methods, and the compound used as the organic layer is an organic small molecule, an organic macromolecule, a polymer or a combination thereof.

[0117] Hole transport layer 4 is a single-layer hole transport layer, including a single-layer hole transport layer containing only one compound and a composite hole transport layer containing multiple compounds. The single-layer hole transport layer can perform both hole injection and hole transport functions. The composite hole transport layer is composed of multiple organic hole materials and is arranged in the industry-standard layout of hole injection layer 3, hole transport layer 4, and electron blocking layer 5.

[0118] In this invention, the hole injection layer 3 is preferably a p-doped hole injection layer, which means a hole injection layer doped with a p-doped agent. A p-doped agent is a material that can impart p-type semiconductor characteristics. P-type semiconductor characteristics refer to the characteristics of injecting or transporting holes at the HOMO energy level, that is, the material characteristics of having high hole conductivity.

[0119] The luminescent layer 6 is located between the hole transport layer 4 and the electron transport layer 8. The host luminescent material is any one or a combination of two of compounds 1 to 208 from the 7-phenylquinolone derivatives of this invention. The guest luminescent material is one of the high-performance DP-1, DP-2, and DP-3 materials, and the preferred mass ratio of the host luminescent material to the guest luminescent material is 96:4. After the above-mentioned functional layer for realizing organic light emission is prepared, an electron transport material is deposited on the luminescent layer 6. The electron transport material is one or a combination of E1, E2, or E3, which have excellent performance in the industry, to obtain the electron transport layer 8. After the electron transport material is deposited, an electron injection material is deposited to form the electron injection layer 9. Then, the cathode 10 is sputtered, and finally, the device is packaged using the industry-standard device packaging method. The sample of the test device is prepared as a 30mm × 30mm sample, and the various luminescent performance indicators and efficiency of the sample are tested. Compared with conventional luminescent materials, the test device has better luminescent performance, efficiency, and stability.

[0120] The following is a comparison and evaluation of organic electroluminescent devices using experimental and control groups:

[0121] The control group samples for the test device, control group 1 to control group 3, were prepared according to the following steps:

[0122] Under vacuum conditions, a 25 nm thick indium tin oxide (ITO) anode is sequentially deposited onto a cleaned conductive glass substrate; a 10 nm thick mixture of HT1 and P1 is deposited as a hole injection layer 3, with P1 used as a p-doper at a mass ratio of 97:3; a 50 nm thick HT-1 is deposited as a hole transport layer 4; and a 10 nm thick EB-1 is deposited as an electron blocking layer 5. After the electron blocking layer 5 is deposited, a 30 nm thick light-emitting layer 6 is fabricated, the structure of which includes one of B-224, B-1346, and B-1348 used in OLED light-emitting layers as the main light-emitting material. B-224, B-1346, and B-1348 are all prior art application numbers 202211327865.X The disclosed compound, in combination with DP-1, DP-2, or DP-3 as the guest luminescent material, with a mass ratio of host luminescent material to guest luminescent material of 96:4; HB-1 with a thickness of 16 nm is deposited on the luminescent layer 6 as a hole blocking layer 7; E1 is deposited on the hole blocking layer 7 with a vacuum deposition thickness of 25 nm as an electron transport layer 8; a 10 nm thick LiF layer is fabricated on the electron transport layer 8 using a vacuum deposition apparatus, this layer serving as an electron injection layer 9; an Al electrode layer with a thickness of 50 nm is fabricated on the electron injection layer 9 using a vacuum deposition apparatus, this layer serving as a cathode 10; finally, a capping material X is deposited on the cathode 10 to form a capping layer 11, which is then encapsulated to complete the fabrication of the test device. Using this method, a device can be prepared as follows... Figure 1 The device shown.

[0123] The detailed composition scheme is as follows:

[0124] Test device control group 1: conductive glass / indium tin oxide (25nm) / HT1:P1=97:3(10nm) / HT-1(50nm) / EB-1(10nm) / B-224:DP-1=96:4(30nm) / HB-1(16nm) / E1(25nm) / LiF(10nm) / Al(50nm).

[0125] Test device control group 2: conductive glass / indium tin oxide (25nm) / HT1:P1=97:3(10nm) / HT-1(50nm) / EB-1(10nm) / B-1346:DP-1=96:4(30nm) / HB-1(16nm) / E1(25nm) / LiF(10nm) / Al(50nm).

[0126] Test device control group 3: conductive glass / indium tin oxide (25nm) / HT1:P1=97:3(10nm) / HT-1(50nm) / EB-1(10nm) / B-1348:DP-1=96:4(30nm) / HB-1(16nm) / E1(25nm) / LiF(10nm) / Al(50nm).

[0127] Test device experimental groups 1 to 3: The preparation method is the same as that of test device control group 1, except that the host luminescent material CDBP is replaced with compound 8 of the present invention, and the mass ratio of host luminescent material to guest luminescent material is 90:10, 99:1, and 96:4, respectively, corresponding to experimental groups 1 to 3.

[0128] Test device experimental groups 4 to 25: The preparation method is the same as that of test device control group 1, except that the main luminescent material CDBP is replaced sequentially with compounds 10, 19, 22, 44, 106, 134, 45, 53, 67, 70, 83, 95, 116, 120, 129, 137, 146, 154, 163, 199, 206, and 208 of this invention.

[0129] Test device experimental groups 26-34: The preparation method is the same as that of test device control group 1, except that the light-emitting layer 6 in this type of experimental group uses a dual host light-emitting material. The selection of the host light-emitting material and the ratio of it to the guest light-emitting material in the light-emitting layer 6 are shown in Table 1:

[0130] Table 1. Ratio of host luminescent material to guest luminescent material in experimental groups 26-34

[0131]

[0132] Note: The “ratio” in the table refers to the mass ratio of the first primary luminescent material, the second primary luminescent material, and the guest luminescent material.

[0133] The conventional material structures used in the fabrication of the above-mentioned test devices are as follows:

[0134] , , , , , , , , , , , , , .

[0135] Display performance data were collected for the control group and experimental group test devices mentioned above. The collected data results are shown in Table 2.

[0136] Table 2. Data Collection Table of Display Performance of Test Devices in Control and Experimental Groups

[0137]

[0138] Note: Tg is the glass transition temperature of the light-emitting layer material under high temperature; the current density during the test device detection process is 15mA / cm; LT90 refers to the time it takes for the brightness of the test device to decay to 90% of the initial brightness; " / " indicates that this type of data was not tested.

[0139] As shown in Table 2, based on the data from the test devices, the test devices prepared using the preferred compound of this invention as the main luminescent material have lower driving voltages, significantly improved thermal stability, and significantly enhanced overall test device efficiency compared to the main luminescent materials in control groups 1 to 3.

[0140] As can be seen from experimental groups 1 to 3 of the present invention, the overall luminescence performance of the main luminescent material is improved in the range of 90:10 to 99:1 in the mass ratio of the main luminescent material to the luminescent layer 6. When the mass percentage is 96%, the luminescence performance of the prepared test device is the best.

[0141] Compared to experimental groups 3-6, 7-9, and 15, the test device data for experimental groups 3-6 are slightly inferior. This may be because compounds 44, 106, 134, and 95 corresponding to experimental groups 7-9 and 15 contain large-volume fully deuterated R substituents. Introducing D atoms into the compound molecules enhances the spin-orbit coupling, which increases the intersystem crossing capability of electrons, improves the radiative transition rate, and reduces the non-radiative transition rate, thereby improving the quantum efficiency of the guest phosphorescent material.

[0142] Compared with experimental groups 1 to 24, experimental groups 26 to 34 of this invention show a significant improvement in overall efficiency. This may be because the preferred compound of this invention is used as a dual-main-body luminescent material, which can effectively balance holes and electrons while forming a wider carrier recombination region, thereby greatly improving the luminescence efficiency of the test device.

[0143] This invention discloses 7-phenylquinolone derivatives and organic electroluminescent devices. When 7-phenylquinolone derivatives are used as the main luminescent material in the luminescent layer of organic electroluminescent devices, they can effectively improve the luminous efficiency and lifespan of organic electroluminescent devices.

[0144] The synthetic route of the 7-phenylquinolone derivatives of this invention is relatively simple and easy to chemically modify, facilitating structural optimization and functional design to meet the performance requirements of different organic electroluminescent devices for the host light-emitting material, thereby accelerating the development of new materials while reducing production costs.

[0145] The synthetic process of the 7-phenylquinolone derivatives of compounds 209 to 420 of this invention is described below:

[0146] The R groups in compounds 209 to 420 are introduced via reactant A', wherein reactant A' is selected from one of A'01 to A'11, and the structural formulas of reactants A'01 to A'11 are shown below:

[0147] , , , , , , , , , , .

[0148] The Y group in compounds 209 to 420 of the present invention is introduced via reactant B, wherein reactant B is selected from one of B1 to B128, and the structural formulas of B1 to B128 are shown below:

[0149] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , .

[0150] Example 5

[0151] The preparation method of compound 223 includes the following steps:

[0152] .

[0153] The preparation methods for S1 and intermediate M1-2 are the same as in Example 1.

[0154] S2. Take a 2.0L three-necked flask and add 111g, 0.5mol of intermediate M1-2, 1.0L of DCM, and 164g, 0.75mol of Boc anhydride in sequence. Stir the mixture at room temperature for 2 hours. After the reaction is complete, concentrate the mixture under reduced pressure to obtain a solid residue. The solid residue is purified by silica gel column chromatography using dichloromethane / n-heptane at a volume ratio of 1:3 to obtain intermediate M10-1, weighing 146g, with a yield of 91%, HPLC purity of 98%, and LC-MS showing a molecular weight of 322.2.

[0155] S3. Under nitrogen protection, a 3.0L three-necked flask was used to add 145g and 0.45mol of intermediate M10-1, 171g and 0.68mol of elemental iodine, 107 and 1.01mol of sodium carbonate, and 1.5L of THF. The mixture was stirred and stirred until homogeneous, and the reaction was carried out at room temperature for 6 hours until the reaction was complete. The organic phase was concentrated, and 2.0L of dichloromethane and 2.0L of water were added sequentially for extraction. The organic phase was dried, filtered, and concentrated to obtain a solid residue. The solid residue was purified by silica gel column chromatography with a volume ratio of dichloromethane / n-heptane of 1:3 to obtain intermediate M10-2, weighing 181g, with a yield of 90%, HPLC purity of 98%, and LC-MS showing a molecular weight of 448.1.

[0156] S4. Under nitrogen protection, a 3.0L three-necked flask was used to add 134g of 0.3mol M10-2, 84g of 0.3mol A'01, and 1500mL of toluene. The mixture was stirred until the solution was clear. Then, 5.5g of 2mmol Pd2(dba)3, 4.0g of 1.5mmol Am-phos, and 58g of 0.6mol sodium tert-butoxide were added. The mixture was then heated to 120℃ and reacted for 10h. After the reaction was completed, the mixture was filtered while hot using diatomaceous earth. The filtrate was cooled to room temperature and washed with purified water. The organic phase was separated and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, dried over anhydrous magnesium sulfate, concentrated, and purified by silica gel column chromatography with dichloromethane / petroleum ether at a volume ratio of 1:2 to obtain intermediate M10-3, weighing 137g, with a yield of 76%, an HPLC purity of 99%, and a molecular weight of 599.3 as shown by LC-MS.

[0157] S5. Under nitrogen protection, a 1.0L three-necked flask was filled with 60g of 0.1mol of M10-3, 500mL of DCM, and 57g of trifluoromethanesulfonic acid. The mixture was stirred at room temperature for 2 hours until the reaction was complete. After the reaction was completed, the solid residue was concentrated under reduced pressure. The solid residue was purified by silica gel column chromatography using dichloromethane / n-heptane at a volume ratio of 1:2 to obtain intermediate M10, weighing 47g, with a yield of 94%, HPLC purity of 98%, and LC-MS showing a molecular weight of 499.3.

[0158] S6. Under nitrogen protection, a 100 mL three-necked flask was filled with 5.0 g (0.01 mol) of M10, 1.6 g (0.01 mol) of 5-chloro-1,3-dicyanobenzene, and 50 mL of toluene. The mixture was stirred until the solution was clear. Then, 0.18 g (0.2 mmol) of Pd2(dba)3, 0.13 g (0.5 mmol) of Am-phos, and 6.5 g (0.02 mol) of cesium carbonate were added. The mixture was then heated to 120 °C and reacted for 10 h. After the reaction was complete, the mixture was filtered hot using diatomaceous earth. The filtrate was cooled to room temperature and washed with purified water. The organic phase was separated and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, dried over anhydrous magnesium sulfate, concentrated, and purified by silica gel column chromatography with dichloromethane / petroleum ether at a volume ratio of 1:2 to obtain compound 223, weighing 4.8 g, with a yield of 77%, an HPLC purity of 99%, and a molecular weight of 625.3 as shown by LC-MS.

[0159] The 1H NMR spectrum data of compound 223 are as follows: Figure 6 As shown: 1 H NMR (500 MHz, CD3OD ) δ 11.06 (s,1H), 8.95 (d, J = 3.1 Hz, 1H), 8.36 (d, J = 3.1 Hz, 1H), 7.91 (t, J = 11.2 Hz, 1H), 7.80 (d, J = 3.0 Hz, 2H), 7.78 – 7.72 (m, 2H), 7.65 – 7.58 (m, 3H), 7.53 – 7.37(m, 6H), 7.32 (d, J = 14.9 Hz, 1H), 1.43 (s, 18H).

[0160] Example 6

[0161] The preparation method of compound 394 includes the following steps:

[0162] .

[0163] S1. Under nitrogen protection, a 3.0L three-necked flask was filled with 134g of 0.3mol M10-2, 70g of 0.3mol compound A'05, 83g of 0.6mol K2CO3, 1200mL THF, and 300mL water. The mixture was stirred and heated to 40℃. After the solution became clear, 6.9g of 6mmol Pd(PPh3)4 was added, and the temperature was raised to 70℃ and the reaction was continued for 12h until the reaction was complete. The reaction solution was cooled to room temperature and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered and concentrated, and purified by silica gel column chromatography with a volume ratio of 1:3 dichloromethane / n-heptane to obtain intermediate M11-1, weighing 124g, with a yield of 81%, HPLC purity of 98%, and LC-MS showing a molecular weight of 510.3.

[0164] S2. The synthesis of intermediate M11 is based on step S5 of the synthesis process of compound 223, except that 60 g and 0.1 mol of intermediate M10-3 are replaced with 51 g and 0.1 mol of intermediate M11-1 to obtain intermediate M11, weighing 39 g, with a yield of 95%, HPLC purity of 98%, and LC-MS showing a molecular weight of 410.3.

[0165] S3. The synthesis of compound 394 is based on step S6 of the synthesis process of compound 223, except that 5.0 g and 0.01 mol intermediate M10 are replaced with 4.1 g and 0.01 mol intermediate M11 to obtain compound 394, weighing 4.4 g, with a yield of 78%, HPLC purity of 99%, and LC-MS showing a molecular weight of 561.3.

[0166] Compound 394 1H NMR data are as follows Figure 7 As shown: 1 H NMR (500 MHz, CD3OD ) δ 10.75 (s,1H), 8.35 (dd, J = 14.8, 3.1 Hz, 1H), 7.96 – 7.88 (m, 2H), 7.79 – 7.60 (m, 4H), 7.55 – 7.33 (m, 8H), 7.11 (d, J = 2.9 Hz, 2H), 1.35 (s, 18H).

[0167] Example 7

[0168] The preparation method of compound 419 includes the following steps:

[0169] .

[0170] S1. The synthesis of intermediate M12-1 follows the same procedure as intermediate M11, except that 70g and 0.3mol of compound A'05 are replaced with 134g and 0.3mol of compound A'08 to obtain intermediate M12-1, weighing 154g, with a yield of 80%, HPLC purity of 98%, and LC-MS showing a molecular weight of 640.3.

[0171] S2. The synthesis of intermediate M12 is based on step S5 of the synthesis process of intermediate M1, except that 60g and 0.1mol of intermediate M10-3 are replaced with 64g and 0.1mol of intermediate M12-1 to obtain compound M12, weighing 50g, with a yield of 93%, HPLC purity of 98%, and LC-MS showing a molecular weight of 540.3.

[0172] S3. The synthesis of compound 431 is based on step S6 of the synthesis process of compound 223, except that 5.0 g and 0.01 mol intermediate M1 are replaced with 5.4 g and 0.01 mol intermediate M8 to obtain compound 419, weighing 5.3 g, with a yield of 72%, HPLC purity of 99%, and LC-MS showing a molecular weight of 741.3.

[0173] The 1H NMR data of compound 419 are as follows: Figure 8 As shown: 1 H NMR (500 MHz, CD3OD ) δ 10.75 (s,1H), 8.45 (dd, J = 14.7, 3.2 Hz, 2H), 8.16 (dt, J = 11.0, 5.6 Hz, 2H), 8.12 –8.03 (m, 2H), 8.02 – 7.89 (m, 2H), 7.82 – 7.33 (m, 21H), 1.69 (s, 6H).

[0174] Following the synthesis methods of Examples 5 to 7, the following compounds were synthesized. The reactants and mass spectrometry (M+1) data of some compounds are shown in Table 3.

[0175] Table 3. Reactants and mass spectrometry data of some compounds from compounds 209 to 420

[0176]

[0177] Based on compounds 209 to 420, the preferred compounds are used as guest luminescent materials in the test device. The basic structure and fabrication method of the test device employ currently recognized device fabrication technologies. A schematic diagram of the test device structure is shown below. Figure 1As shown, the fabrication process of the test device is described in detail below:

[0178] The experimental setup consisted of five main parts: an anode (2), a hole transport layer (4), a light-emitting layer (6), an electron transport layer (8), and a cathode (10). Any one or any combination of two compounds 209 to 420 was used in the light-emitting layer (6) as a guest luminescent material for evaluation. A brief description of the setup preparation is as follows:

[0179] The substrate 1 is made of glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. In this test, ITO conductive glass was used. Furthermore, the substrate 1 used for displays can also have a positive array of thin-film transistors, and specific display images formed by the combination of these positive arrays.

[0180] The organic layer includes a hole transport layer 4, a light-emitting layer 6, and an electron transport layer 8. The hole transport layer 4 is located between the anode 2 and the light-emitting layer 6, and the electron transport layer 8 is located between the cathode 10 and the light-emitting layer 6. The light-emitting layer 6 is composed of a host light-emitting material and a guest light-emitting material. The host light-emitting material is a high-performance material... , , , One of the materials is a guest luminescent material, which is any one of compounds 209 to 420 of the present invention, and the mass ratio of the host luminescent material to the guest luminescent material is 90:10 to 99:1.

[0181] Anode 2 is used to facilitate the injection of holes into the organic layer. It is preferably made of a material with a high work function. Anodes that can be used in this invention include indium tin oxide, indium zinc oxide, tin dioxide, or zinc oxide.

[0182] The cathode 10 is designed to facilitate the injection of electrons into the organic layer. It is preferably made of a material with a low work function, including metals, alloys, or organic combinations thereof. Cathodes applicable to this invention include magnesium, silver, aluminum, aluminum-lithium, calcium, magnesium-indium, or magnesium-silver.

[0183] The functional organic layer is formed by vacuum thermal evaporation, spin coating or printing methods, and the compound used as the organic layer is an organic small molecule, an organic macromolecule, a polymer or a combination thereof.

[0184] Hole transport layer 4 is a single-layer hole transport layer, including a single-layer hole transport layer containing only one compound and a composite hole transport layer containing multiple compounds. The single-layer hole transport layer can perform both hole injection and hole transport functions. The composite hole transport layer is composed of multiple organic hole materials and is arranged in the industry-standard layout of hole injection layer 3, hole transport layer 4, and electron blocking layer 5.

[0185] In this invention, the hole injection layer is preferably a p-doped hole injection layer, which means a hole injection layer doped with a p-doped agent. A p-doped agent is a material that can impart p-type semiconductor characteristics. P-type semiconductor characteristics refer to the ability to inject or transport holes at the HOMO energy level, i.e., the material characteristics of high hole conductivity.

[0186] The luminescent layer 6 is located between the hole transport layer 4 and the electron transport layer 8. The host luminescent material is one of the high-performance materials PH-1, PH-2, PH-3, PH-4, and PH-5, and the guest luminescent material is any one of compounds 209 to 420. The preferred mass ratio of the host luminescent material to the guest luminescent material is 90:10 to 99:1. After the above-mentioned functional layer for organic light emission is prepared, an electron transport material is deposited on the luminescent layer 6. The electron transport material can be one or more combinations of E1, E2, or E3, which have excellent performance in the industry, to obtain the electron transport layer 8. After the electron transport material is deposited, an electron injection material is deposited to form the electron injection layer 9. Then, a metal cathode 10 is sputtered, and finally, the device is packaged using a common industry-standard device packaging method. The test device is fabricated into a 30mm × 30mm sample, and the various luminescent performance indicators and efficiency of the sample are tested. Compared with conventional luminescent materials, the device exhibits superior luminescent performance, efficiency, and stability.

[0187] The control group samples for the test devices, control group 4 to control group 6, were prepared according to the following steps:

[0188] Under vacuum conditions, a 25 nm thick indium tin oxide (ITO) anode is sequentially deposited onto a cleaned conductive glass substrate; a 10 nm thick mixture of HT1 and P1 is deposited as a hole injection layer 3, with P1 used as a p-doper, and the mass ratio of the two is 97:3; a 50 nm thick HT-1 is deposited as a hole transport layer 4; a 10 nm thick EB-1 is deposited as an electron blocking layer 5; after the electron blocking layer 5 is deposited, a 30 nm thick light-emitting layer 6 is fabricated, the structure of which includes PH-4 or PH-5 used in OLED light-emitting layers, with PH-4 or PH-5 as the host light-emitting material, and one of B-224, B-1346, and B-1348 as the guest light-emitting material, and B-224, B-1346, and B- Compounds 1348 are all compounds disclosed in prior art application number 202211327865.X, and the mass ratio of the host luminescent material to the guest luminescent material is 96:4. On the luminescent layer 6, a 16nm thick HB-1 film is deposited as a hole-blocking layer 7. On the hole-blocking layer 7, E1 is deposited, with a vacuum evaporation film thickness of 25nm, as an electron transport layer 8. On the electron transport layer 8, a 10nm thick LiQ layer is fabricated using a vacuum evaporation apparatus; this layer is the electron injection layer 9. On the electron injection layer 9, a 50nm thick Al electrode layer is fabricated using a vacuum evaporation apparatus; this layer is the cathode 10. Finally, a capping layer material X-1 is deposited on the cathode 10 to form a capping layer 11, which is then encapsulated to complete the fabrication of the test device. Using this method, the following can be obtained: Figure 1 As shown.

[0189] The detailed composition scheme is as follows:

[0190] Test device control group 4: Indium Tin Oxide (25nm) / HT1:P1=97:3(10nm) / HT-1(50nm) / EB-1(10nm) / PH-4: B-224=96:4(30nm) / HB-1(16nm) / E1(25nm) / LiQ(10nm) / Al(50nm).

[0191] Test device control group 5: Indium Tin Oxide (25nm) / HT1:P1=97:3(10nm) / HT-1(50nm) / EB-1(10nm) / PH-4: B-1346=96:4(30nm) / HB-1(16nm) / E1(25nm) / LiQ(10nm) / Al(50nm).

[0192] Test device control group 6: Indium Tin Oxide (25nm) / HT1:P1=97:3(10nm) / HT-1(50nm) / EB-1(10nm) / PH-4: B-1348=96:4(30nm) / HB-1(16nm) / E1(25nm) / LiQ(10nm) / Al(50nm).

[0193] Test device experimental groups 35 to 64: The preparation method is the same as that of test device control group 4, except that the guest luminescent material BD-1 is replaced with the compound of the present invention. The specific replacement compounds are shown in Table 4.

[0194] Table 4. List of guest luminescent materials corresponding to experimental groups 35 to 64

[0195]

[0196] The conventional material structures used in the fabrication of the above-mentioned test devices are as follows:

[0197] , , , , , , , , , , , , , .

[0198] Display performance data were collected for the control group and experimental group test devices mentioned above. The collected data results are shown in Table 5.

[0199] Table 5. Data Collection Table of Display Performance of Test Devices in Control and Experimental Groups

[0200]

[0201] Note: Tg is the glass transition temperature of the light-emitting layer material under high temperature; the current density during the detection process of the testing device is 15 mA / cm². 2 YT90 refers to the time it takes for the brightness of the test device to decay to 90% of its initial brightness.

[0202] As shown in Table 5, the test data of the test devices in experimental groups 35 to 64 show that, compared with the guest luminescent materials in control groups 4 to 6, the test devices prepared using the preferred compound of this invention as the guest luminescent material have lower driving voltage, significantly improved thermal stability, significantly extended service life, and significantly improved overall test device efficiency, which has potential value for its promotion and application.

[0203] Compared to experimental groups 35-47, 57-64, and 48-56, the test data of experimental groups 35-47 and 57-64 are slightly inferior. This may be because compounds 337, 339, 342, 344, 346, 348, 357, 361, and 366 in experimental groups 48-56 contain fully deuterated carbazole substituents. Introducing D atoms into the compound molecules enhances the spin-orbit coupling, increasing the intersystem crossing capability of electrons, improving the radiative transition rate, and reducing the non-radiative transition rate. This, in turn, improves the quantum efficiency of the guest luminescent material and the lifespan of the test device.

[0204] Comparing test devices prepared with a single host material, the overall efficiency of test devices in experimental groups 35-64 of this invention is significantly improved compared to experimental groups 1-25. This may be because the R groups in the compounds corresponding to experimental groups 35-64 have large steric hindrance, which helps to suppress the formation of intermolecular hydrogen bonds by carbonyl groups. At the same time, the Y groups in the compounds corresponding to experimental groups 35-64 are all electron-withdrawing groups. This design promotes effective intramolecular polarization of the compounds, enhances electrical transport properties and improves quantum efficiency, thereby improving the overall performance of the test devices.

[0205] When compounds 209 to 420 of the present invention are used as guest luminescent materials in the luminescent layer of organic electroluminescent devices, they can effectively improve the luminous efficiency and lifespan of organic electroluminescent devices.

[0206] The synthetic routes of compounds 209 to 420 of this invention are relatively simple, and the main structure is easy to chemically modify, which facilitates structural optimization and functional design to meet the material performance requirements of different organic electroluminescent devices, accelerate the development of new materials, and reduce production costs.

[0207] The preferred embodiments of the present invention have been described in detail above. However, the present invention is not limited to the above embodiments. Within the scope of knowledge possessed by those skilled in the art, various changes can be made without departing from the spirit of the present invention. Many other changes and modifications can be made without departing from the concept and scope of the present invention. It should be understood that the present invention is not limited to the specific embodiments, and the scope of the present invention is defined by the appended claims.

Claims

1. A 7-phenylquinolone derivative, characterized in that, The structural formula of the 7-phenylquinolone derivatives is shown in general formula 1: 7-Phenylonone derivatives are formed by Y bonded to the main structure via single bonds. The structural formula of the main structure is as follows: ; The structural formula for R is: ； The structural formula for Y is: ； In y107, L1 and L2 are independently selected from H and C1~C, respectively. 10 Alkyl or C3~C 10 cycloalkyl groups; Wherein, * indicates the position bonded to the main structure. Among them, r10, r16, r24, r33, r37, r46, r56, r58, r67, r68, r136, r141, r142, r145, r146, r151, r152, r155, r156, r158, r159, r165, r167, and r173 are all bonded to the main structure through only one *. y1~y7, y9, y11, y12, y17, y18, y21, y22, y95, and y105 are all bonded to the main structure through only one *.

2. The 7-phenylquinolone derivative according to claim 1, characterized in that, The structural formula of the 7-phenylquinolone derivative is: 。 3. A primary luminescent material, characterized in that, Compounds selected from claims 2, including compounds 7, 8, 10, 11, 18, 19, 22, 29, 38, 39, 42-45, 53-55, 66, 67, 70, 71, 82-84, 87-91, 95, 104-106, 115-121, and 125. Any one of compounds 129, 134, 137, 138, 146-147, 154, 163, 169, 170, 172, 173, 175, 176, 178-180, 182, 184, 185, 187-196, 199, 204, 206-208.

4. A guest luminescent material, characterized in that, The compound is selected from any one of compounds 209-228, 230, 231, 233-239, 241, 243-245, 254, 256, 266, 268, 269, 272, 274-278, 282, 283, 305, 306, 309-314, 327-329, 332, 333, 336-367, 369, 370, 385-388, 394, 395, 403-407, 409, 417, 418, and 420 of claim 2.

5. An organic electroluminescent device, comprising a cathode (10), an anode (2), and an organic layer located between the cathode (10) and the anode (2), wherein the organic layer is composed of a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light-emitting layer (6), a hole blocking layer (7), an electron transport layer (8), and an electron injection layer (9) stacked sequentially from bottom to top, wherein the hole injection layer (3) is deposited on the anode (2), the anode (2) is loaded on a substrate (1), and a capping layer (11) is further disposed on the cathode (10), characterized in that, The light-emitting layer (6) is made of the main light-emitting material as described in claim 3.

6. An organic electroluminescent device, comprising a cathode (10), an anode (2), and an organic layer located between the cathode (10) and the anode (2), wherein the organic layer is composed of a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light-emitting layer (6), a hole blocking layer (7), an electron transport layer (8), and an electron injection layer (9) stacked sequentially from bottom to top, wherein the hole injection layer (3) is deposited on the anode (2), the anode (2) is loaded on a substrate (1), and a capping layer (11) is further disposed on the cathode (10), characterized in that, The light-emitting layer (6) is made of the guest light-emitting material as described in claim 4.

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