A benzophenanthroline compound and its application

Abstract

The present invention provides a new benzophenanthroline compound having a structure shown in Formula I. The present invention not only has good electron injection and transmission capabilities, but also has good Li ion binding capabilities by introducing an anthracene group or a triazine group into the benzophenanthroline structure. The dopant Li can interact with the nitrogen atom in the benzophenanthroline compound structure provided by the present invention to form an ionic bond, which can prevent Li ions from diffusing into adjacent functional layers, thereby preventing the efficiency and life of the device from being reduced. The driving voltage of the device is reduced, the efficiency and life of the device are improved, and the stability and reliability of the device are improved.

Description

Technical Field

[0001] The invention relates to the technical field of organic electroluminescent materials, in particular to a benzophenanthroline compound and application thereof. Background Art

[0002] In organic light-emitting diodes (OLEDs), stacked devices have higher efficiency and lifespan than single-layer devices, and have greater application prospects, so the development of stacked devices has received increasing attention from the industry in recent years. Stacked devices have two or more light-emitting layers, and the two light-emitting layers are connected by a CGL layer (charge generation layer). The currently commonly used CGL layer is usually formed by metal lithium or metal ytterbium (Yb) doped in an electron transport material (ETL). However, due to the strong metallic activity of Li and the strong diffusion ability of Li ions, the ETL material not only needs to have good electron injection and transmission capabilities, but also needs to have a certain Li ion binding ability to prevent Li ions from diffusing into adjacent functional layers and affecting the performance of the device. At present, conventional ETL can play the role of CGL, but lacks the ability to bind Li ions and cannot meet the performance requirements of the CGL layer. Summary of the invention

[0003] In view of this, the technical problem to be solved by the present invention is to provide a benzophenanthroline compound and its application, which improves the characteristics of electron injection and transmission, thereby reducing the driving voltage of the device, improving the efficiency and life, and enhancing the stability of the device.

[0004] The present invention provides a benzophenanthroline compound having a structure shown in Formula I:

[0005]

[0006] Among them, R 1 is selected from hydrogen, deuterium, halogen, a C1-C20 straight or branched aliphatic group or a C3-C30 cycloalkane group;

[0007] m is any integer from 1 to 7;

[0008] Ar 1 ,Ar 2 independently selected from substituted or unsubstituted C6-C60 aryl or C4-C60 heteroaryl;

[0009] L is selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a C4-C60 heteroarylene group, and a combination thereof;

[0010] A has the structure shown in Formula II or Formula III:

[0011]

[0012] R 2 Selected from hydrogen, deuterium, halogen, C1-C20 straight or branched aliphatic group, C3-C30 cycloalkane group, substituted or unsubstituted C6-C60 aryl group or C4-C60 heteroaryl group;

[0013] n is any integer from 1 to 9;

[0014] R 3 , R 4 independently selected from H, substituted or unsubstituted C6-C60 aryl or C4-C60 heteroaryl;

[0015] # indicates the connection location.

[0016] The present invention provides an organic light-emitting device, comprising an anode, a cathode, a first stack and a second stack located between the anode and the cathode, and at least one charge generation layer located between the first stack and the second stack, wherein the charge generation layer contains at least one of the above-mentioned benzophenanthroline compounds.

[0017] The present invention provides an organic light-emitting device, comprising an anode, a cathode, a first stack and a second stack located between the anode and the cathode, and at least one electron blocking layer located between the first stack and the second stack, wherein the electron blocking layer contains at least one of the above-mentioned benzophenanthroline compounds.

[0018] The present invention provides an organic light-emitting device, comprising an anode, a cathode, a first stack and a second stack located between the anode and the cathode, and at least one electron transport layer located between the first stack and the second stack, wherein the electron transport layer contains at least one of the above-mentioned benzophenanthroline compounds.

[0019] The present invention provides a display panel, comprising the above organic light-emitting device.

[0020] The invention provides a new benzophenanthroline compound, which not only improves the electron transmission ability of the compound by introducing an anthracene group or a triazine group, but also retains the good binding ability of benzophenanthroline to dopant metal ions. The dopant metal ions can interact with the nitrogen atoms in the benzophenanthroline compound structure provided by the invention to form ionic bonds, which can prevent the metal ions from diffusing into adjacent functional layers, thereby preventing the efficiency and life of the device from being reduced. The introduction of anthracene group or a triazine group reduces the driving voltage of the device and improves the efficiency and life of the device, while improving the stability and reliability of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0021] Figure 1 This is a schematic structural diagram of the organic light-emitting device provided by the present invention. DETAILED DESCRIPTION

[0022] The present invention provides a benzophenanthroline compound having a structure shown in Formula I:

[0023]

[0024] Among them, R 1 is selected from hydrogen, deuterium, halogen, a C1-C20 straight or branched aliphatic group or a C3-C30 cycloalkane group;

[0025] m is any integer from 1 to 7;

[0026] Ar 1 ,Ar 2 independently selected from substituted or unsubstituted C6-C60 aryl or C4-C60 heteroaryl;

[0027] L is selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a C4-C60 heteroarylene group, and a combination thereof;

[0028] A has the structure shown in Formula II or Formula III:

[0029]

[0030] R 2 Selected from hydrogen, deuterium, halogen, C1-C20 straight or branched aliphatic group, C3-C30 cycloalkane group, substituted or unsubstituted C6-C60 aryl group or C4-C60 heteroaryl group;

[0031] n is any integer from 1 to 9;

[0032] R 3 , R 4 independently selected from H, substituted or unsubstituted C6-C60 aryl or C4-C60 heteroaryl;

[0033] # indicates the connection location.

[0034] Optionally, m is any integer from 1 to 3, including but not limited to 1, 2 or 3.

[0035] Optional, R 1 Selected from hydrogen, deuterium, halogen, C1-C10 straight or branched alkyl or C3-C6 cycloalkane group.

[0036] Optional, R 1 Selected from hydrogen, deuterium, halogen, C1-C6 straight or branched alkyl or C3-C6 cycloalkane group.

[0037] Optional, R 1 Selected from hydrogen, C1-C6 straight chain or branched alkyl.

[0038] Optional, R 1 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl.

[0039] Optional, Ar 1 ,Ar 2 are independently selected from substituted or unsubstituted monocyclic aryl or monocyclic heteroaryl.

[0040] Optionally, the heteroatom of the monocyclic heteroaryl group is selected from one or more of N, O and S.

[0041] Optional, Ar 1 ,Ar 2 are independently selected from substituted or unsubstituted phenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl or triazinyl.

[0042] Optional, Ar 1 ,Ar 2 The substituents in are independently selected from one or more of deuterium, halogen, cyano, nitro, amino, and C1-C10 alkyl.

[0043] Optionally, L is selected from a single bond, a substituted or unsubstituted phenylene or a pyridylene.

[0044] Optionally, L is selected from a single bond, a substituted or unsubstituted phenylene group.

[0045] Optionally, the phenylene group may be further substituted by a phenyl group or a C1-C6 straight-chain or branched-chain alkyl group.

[0046] Optionally, the phenylene group may be further substituted by any one or more of phenyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl.

[0047] Optional, R 2 It is selected from hydrogen, deuterium, halogen, C1-C10 straight or branched alkyl, C3-C6 cycloalkane group, substituted or unsubstituted monocyclic aromatic group or four to six-membered monocyclic heteroaromatic group and combinations thereof.

[0048] In the present invention, the above combination means condensation or connection via a single bond.

[0049] Optionally, the heteroatom of the heteroaryl group is selected from one or more of N, O and S.

[0050] Optional, R 2is selected from hydrogen, deuterium, halogen, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclobutyl, phenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, naphthyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, fluorenyl, carbazolyl, dibenzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl or benzotriazolyl.

[0051] Optionally, the above R 2 The substituent is selected from one or more of deuterium, halogen, cyano, nitro, amino, and C1-C10 alkyl.

[0052] Optional, R 2 is selected from hydrogen, deuterium, naphthyl, dibenzofuranyl, N-methylbenzimidazolyl or N-ethylbenzimidazolyl.

[0053] Optionally, n is any integer from 1 to 3.

[0054] Optional, n is 1 or 2.

[0055] Optional, R 3 , R 4 Independently selected from H, substituted or unsubstituted monocyclic aryl or four- to six-membered monocyclic heteroaryl and combinations thereof.

[0056] In the present invention, the above combination means condensation or connection via a single bond.

[0057] Optionally, the heteroatom of the heteroaryl group is selected from one or more of N, O and S.

[0058] Optional, R 3 , R 4 The radicals are independently selected from substituted or unsubstituted phenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, naphthyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl or biphenyl.

[0059] Optional, R 3 , R 4 The substituent is selected from one or more of deuterium, halogen, cyano, nitro, amino, and C1-C10 alkyl.

[0060] Optionally, the above-mentioned benzophenanthroline compound has any of the following structures:

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067] The present invention provides an organic light-emitting device, comprising an anode, a cathode, a first stack and a second stack located between the anode and the cathode, and at least one charge generation layer located between the first stack and the second stack, wherein the charge generation layer contains at least one of the above-mentioned benzophenanthroline compounds.

[0068] The present invention provides an organic light-emitting device, comprising an anode, a cathode, a first stack and a second stack located between the anode and the cathode, and at least one electron blocking layer located between the first stack and the second stack, wherein the electron blocking layer contains at least one of the above-mentioned benzophenanthroline compounds.

[0069] The present invention provides an organic light-emitting device, comprising an anode, a cathode, a first stack and a second stack located between the anode and the cathode, and at least one electron transport layer located between the first stack and the second stack, wherein the electron transport layer contains at least one of the above-mentioned benzophenanthroline compounds.

[0070] Optionally, the charge generation layer is an n-type charge generation layer.

[0071] Optionally, the n-type charge generation layer is composed of a metal or an n-type doped organic material, wherein the metal is selected from Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Ce, Sm, Eu, Tb, Dy or Yb.

[0072] The organic electroluminescent device provided by the present invention may be an organic light-emitting device well known to those skilled in the art. Optionally, the first stack includes one or more layers of a hole injection layer, a hole transport layer, and an electron blocking layer. Optionally, the second stack includes one or more layers of a hole blocking layer, an electron transport layer, and an electron injection layer.

[0073] Optionally, the anode material of the organic electroluminescent device can be selected from metals such as copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, etc. and their alloys; such as metal oxides such as indium oxide, zinc oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; such as conductive polymers such as polyaniline, polypyrrole, poly (3-methylthiophene), etc., in addition to the above materials that facilitate hole injection and their combinations, also include known materials suitable for anodes.

[0074] Optionally, the cathode material of the organic electroluminescent device can be selected from metals such as aluminum, magnesium, silver, indium, tin, titanium, etc. and their alloys; such as multilayer metal materials such as LiF / Al, LiO2 / Al、BaF 2 / Al, etc.; in addition to the above materials that facilitate electron injection and their combinations, also include known materials suitable for use as cathodes.

[0075] According to the present invention, when the n-type charge generation layer is doped with an alkali metal, the alkali metal diffuses into the p-type charge generation layer to minimize the diffusion of the alkali metal in order to firmly penetrate into the main compound o-phenanthroline compound, thereby using an organic electroluminescent device.

[0076] In some embodiments of the present invention, the charge generation layer, one or more light-emitting units in the organic electroluminescent device are doped with the above-mentioned benzophenanthroline compound.

[0077] Optionally, the organic light-emitting device is prepared according to the following method:

[0078] An anode is formed on a transparent or opaque smooth substrate, and a first stack, a charge generation layer, a second stack, and a cathode are sequentially formed on the anode.

[0079] Optionally, in the present invention, the first stack, the charge generating layer, the second stack, and the cathode may be formed by known film forming methods such as evaporation, sputtering, spin coating, dipping, and ion plating.

[0080] In the present invention, the above-mentioned organic electroluminescent device (OLED device) can be used in a display device, wherein the organic light-emitting display device can be a mobile phone display, a computer display, a TV display, a smart watch display, a smart car display panel, a VR or AR helmet display, a display of various smart devices, etc.

[0081] The present invention provides a display panel, comprising the above organic light-emitting device.

[0082] The present invention also provides a display device, comprising the above display panel.

[0083] The following will be described clearly and completely in conjunction with the technical solutions of the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0084] Example

[0085] Example 1: Synthesis of Compound H5

[0086]

[0087] 1) Synthesis of intermediate 1-2

[0088] Compound 1-1 (30.1 g, 0.1 moL) and acetaldehyde aqueous solution (0.12 moL) were added to 500 mL of tetrahydrofuran solution, and then p-toluenesulfonic acid monohydrate (2.38 g, 25.3 mmoL) was added, the temperature was raised to reflux, and the mixture was stirred for 16 h. After the reaction was complete, the reaction solution was cooled to room temperature and neutralized with saturated sodium bicarbonate. The organic layer was separated, the aqueous solution was extracted with toluene three times, the organic phases were combined, the organic layer was dried over anhydrous sodium sulfate, and the organic phase was concentrated to obtain a semi-dried solid. The solid was purified by column chromatography with ethyl acetate and n-hexane (1:5) to obtain the target intermediate 1-2 (25 g, yield 81%). LC-MS: M / Z 308.98 (M + ).

[0089] 2) Synthesis of intermediates 1-4

[0090] Compound 1-2 (20 g, 64.7 mmoL) and compound 1-3 (21.5 g, 77.6 mmoL) were added to anhydrous toluene (400 mL), stirred evenly, replaced with nitrogen 3 times, and then anhydrous potassium carbonate (25.6 g, 186 mmoL) and tetrakistriphenylphosphine palladium (1.8 g, 1.5 mmoL) were added thereto. Nitrogen protection was introduced, the temperature was raised to reflux, the produced water was separated, and stirred for 16 hours. After the reaction was complete, it was cooled to room temperature, the solution was washed with saturated ammonium chloride 3 times, layered, the aqueous phase was extracted with toluene 3 times, the organic phases were combined, the organic phases were dried with saturated sodium sulfate, distilled under reduced pressure, and concentrated to semi-dry solids. Using ethyl acetate and n-hexane as developing solvents, the semi-dry solids were purified by column chromatography to obtain the target intermediate 1-4 (21 g, 70.4%). LC-MS: M / Z 462.18 (M + ).

[0091] 3) Synthesis of intermediate H5

[0092] Dissolve the intermediate 1-4 (10 g, 21.7 mg) in 100 mL of anhydrous tetrahydrofuran solution, stir evenly, protect with nitrogen, cool the liquid nitrogen to -70 ° C, slowly drop n-butyl lithium tetrahydrofuran solution, after the dropwise addition is complete, slowly heat to room temperature 0 ° C and continue to stir for 1 hour, slowly inject 2 mL of bromobenzene at 0 ° C, after the injection is complete, keep warm for 3 hours, then heat to room temperature 25 ° C, and continue to stir for 3 hours. After the reaction is complete, slowly inject 50 mL of distilled water to quench the reaction, the temperature does not exceed 50 ° C, separate the organic phase, wash the organic phase with saturated sodium chloride solution 3 times, extract the aqueous phase with toluene 3 times, combine the organic phases, dry with saturated sodium sulfate, filter, and concentrate the organic phase. Obtain a semi-dried solid. Use ethyl acetate and n-hexane as developing solvents, use column chromatography to purify the semi-dried solid to obtain the target product H5 (9.2 g, 69.2%). LC-MS: M / Z 614.23 (M + ).

[0093] Example 2: Synthesis of Compound H32

[0094]

[0095]

[0096] 1) Synthesis of intermediate 2-2

[0097] Compound 2-1 (37.7 g, 0.1 moL) and acetaldehyde aqueous solution (0.12 moL) were added to 500 mL of tetrahydrofuran solution, and then p-toluenesulfonic acid monohydrate (2.38 g, 25.3 mmol) was added, the temperature was raised to reflux, and stirred for 16 h. After the reaction was complete, the reaction solution was cooled to room temperature and neutralized with saturated sodium bicarbonate. The organic layer was separated, the aqueous solution was extracted with toluene three times, the organic phases were combined, the organic layer was dried over anhydrous sodium sulfate, and the organic phase was concentrated to obtain a semi-dry solid. The solid was purified by column chromatography with ethyl acetate and n-hexane (1:5) to obtain the target intermediate 2-2 (27.2 g, yield 70.6%). LC-MS: M / Z386.27 (M + ).

[0098] 2) Synthesis of intermediate 2-4

[0099] Compound 2-2 (20 g, 52 mmoL) and compound 2-3 (21.5 g, 77.6 mmoL) were added to anhydrous toluene (400 mL), stirred evenly, replaced with nitrogen 3 times, and then anhydrous potassium carbonate (25.6 g, 186 mmoL) and tetrakis triphenylphosphine palladium (1.8 g, 1.5 mmoL) were added thereto. Nitrogen protection was introduced, the temperature was raised to reflux, the produced water was separated, and stirred for 16 h. After the reaction was complete, it was cooled to room temperature, the solution was washed with saturated ammonium chloride 3 times, layered, the aqueous phase was extracted 3 times with toluene, the organic phases were combined, the organic phases were dried with saturated sodium sulfate, distilled under reduced pressure, and concentrated to semi-dry solids. Using ethyl acetate and n-hexane as developing solvents, the semi-dry solids were purified by column chromatography to obtain the target intermediate 2-4 (24.3 g, 87.1%). LC-MS: M / Z 538.61 (M + ).

[0100] 3) Synthesis of intermediate H32

[0101] Dissolve the intermediate 2-4 (10 g, 18.6 mg) in 100 mL of anhydrous tetrahydrofuran solution, stir evenly, protect with nitrogen, cool the liquid nitrogen to -70 ° C, slowly add n-butyl lithium tetrahydrofuran solution, after the addition is complete, slowly heat to room temperature 0 ° C and continue to stir for 1 hour, slowly inject 2 mL of bromobenzene at 0 ° C, after the injection is complete, keep warm for 3 hours, then heat to room temperature 25 ° C, and continue to stir for 3 hours. After the reaction is complete, slowly inject 50 mL of distilled water to quench the reaction, the temperature does not exceed 50 ° C, separate the organic phase, wash the organic phase with saturated sodium chloride solution 3 times, extract the aqueous phase with toluene 3 times, combine the organic phases, dry with saturated sodium sulfate, filter, and concentrate the organic phase. Obtain a semi-dried solid. Use ethyl acetate and n-hexane as developing solvents, use column chromatography to purify the semi-dried solid to obtain the target product H32 (10.4 g, 81.2%). LC-MS: M / Z614.23 (M + ).

[0102] Example 3: Synthesis of Compound H24

[0103]

[0104]

[0105] 1) Synthesis of intermediate 3-3

[0106] Compound 3-1 (33.6 g, 0.1 moL) and compound 3-2 (15.5 g, 0.9 moL) were added to anhydrous toluene (500 mL), stirred evenly, replaced with nitrogen 3 times, and then anhydrous potassium carbonate (27.6 g, 0.2 moL) and tetrakistriphenylphosphine palladium (1.8 g, 1.5 mmoL) were added thereto. Nitrogen protection was introduced, the temperature was raised to reflux, the produced water was separated, and stirred for 16 hours. After the reaction was complete, it was cooled to room temperature, the solution was washed with saturated ammonium chloride 3 times, separated, the aqueous phase was extracted with toluene 3 times, the organic phases were combined, the organic phases were dried with saturated sodium sulfate, distilled under reduced pressure, and concentrated to semi-dry solids. The semi-dry solids were purified by column chromatography using ethyl acetate and n-hexane as developing solvents to obtain the target intermediate 3-3 (29.5 g, 77%). LC-MS: M / Z384.30 (M + ).

[0107] 2) Synthesis of intermediate 3-4

[0108] Compound 3-3 (20g, 52.2mmoL) was dissolved in anhydrous tetrahydrofuran solution (200mL), replaced with nitrogen and protected, magnesium chips (1.5g, 62mmoL) after oxide removal were added, stirred and 4-5 iodine particles were added, heated to reflux, and the color of the reaction solution changed from deep red to cyan, cooled to -70°C, trimethyl borate (6.5g, 62mmoL) was slowly added to the reaction solution, and the temperature was slowly raised to room temperature after the addition was completed, and the temperature was kept and stirred for 2h. After the reaction was complete, 100mL of distilled water was slowly added, and the temperature was controlled to be less than 50°C. The reaction solution was separated, the organic phase was washed 3 times with saturated distilled water, the aqueous phase was extracted 3 times with toluene solution, the organic phase was combined, the organic phase was dried with saturated sodium sulfate, distilled under reduced pressure, and concentrated to a semi-dry solid. The semi-dry solid was purified by column chromatography using ethyl acetate and n-hexane as developing solvents to obtain the target intermediate 3-4 (7.8g, 43%). LC-MS: M / Z 349.18 (M + ).

[0109] 3) Synthesis of intermediate 3-5

[0110] Compound 2-2 (20 g, 64.7 mmoL) and compound 3-4 (27 g, 77.6 mmoL) were added to anhydrous toluene (400 mL), stirred evenly, replaced with nitrogen 3 times, and then anhydrous potassium carbonate (25.6 g, 186 mmoL) and tetrakistriphenylphosphine palladium (1.8 g, 1.5 mmoL) were added thereto. Nitrogen protection was introduced, the temperature was raised to reflux, the produced water was separated, and stirred for 16 h. After the reaction was complete, it was cooled to room temperature, the solution was washed with saturated ammonium chloride 3 times, separated, the aqueous phase was extracted with toluene 3 times, the organic phases were combined, the organic phases were dried with saturated sodium sulfate, distilled under reduced pressure, and concentrated to semi-dry solids. The semi-dry solids were purified by column chromatography using ethyl acetate and n-hexane as developing solvents to obtain the target intermediate 3-5 (22.2 g, 56.3%). LC-MS: M / Z 609.72 (M + ).

[0111] 4) Synthesis of intermediate H24

[0112] Dissolve the intermediate 3-5 (10 g, 16.4 mmol) in 100 mL of anhydrous tetrahydrofuran solution, stir evenly, protect with nitrogen, cool the liquid nitrogen to -70 ° C, slowly add n-butyl lithium tetrahydrofuran solution, after the addition is complete, slowly heat to room temperature 0 ° C and continue to stir for 1 hour, slowly inject 2 mL of bromobenzene at 0 ° C, after the injection is complete, keep warm for 3 hours, then heat to room temperature 25 ° C, and continue to stir for 3 hours. After the reaction is complete, slowly inject 50 mL of distilled water to quench the reaction, the temperature does not exceed 50 ° C, separate the organic phase, wash the organic phase with saturated sodium chloride solution 3 times, extract the aqueous phase with toluene 3 times, combine the organic phases, dry with saturated sodium sulfate, filter, and concentrate the organic phase. Obtain a semi-dried solid. Use ethyl acetate and n-hexane as developing solvents, use column chromatography to purify the semi-dried solid to obtain the target product H24 (8.2 g, 65.5%). LC-MS: M / Z 761.83 (M + ).

[0113] Example 4: H37 was prepared in a similar manner.

[0114] Example 5: H26 was prepared in a similar manner.

[0115] Example 6: H30 was prepared in a similar manner.

[0116] Device implementation scheme 1 Figure 1 As shown, the organic electroluminescent device of the present invention comprises a substrate (10), an anode (20), a first hole transport layer (30), a first light-emitting unit (40) comprising a main body and a dopant, a charge generation layer (50) comprising a P-type charge generation layer and an N-type charge generation layer, a second hole transport layer (60), a second light-emitting unit (70) comprising a main body and a dopant, an electron transport layer (80) and a cathode (90). In addition, the device provided by the present invention may also include a hole injection layer, an electron injection layer or a second electron transport layer. Specific preparation steps: In a vacuum environment, the following organic film layers are thermally deposited in sequence on an ITO glass substrate:

[0117] 1: Hole injection layer, compounds HT and HI are co-deposited on the ITO electrode to form a 10nm organic film layer, with a volume ratio of (97:3);

[0118] 2: The first hole transport layer, compound HT is evaporated onto the hole injection layer to form a 60nm organic film layer;

[0119] 3: In the first light-emitting unit, compound H1 and compound D1 are co-deposited on the hole transport layer to form a 20 nm organic film layer with a volume ratio of (98:2);

[0120] 4: The first electron transport layer, compound ET and Liq are co-deposited on the light-emitting layer to form a 20nm organic film layer, with a volume ratio of (50:50);

[0121] 5: Charge generation layer, compound H5 and Yb are co-deposited on the light-emitting layer to form a 10nm organic film layer, in which the doping ratio of Yb is 2%, forming an N-type charge generation layer; compound HT and HI jointly form a 10nm organic film layer with a volume ratio of (97:3), forming a P-type charge generation layer.

[0122] 6: The second hole transport layer, compound HT is evaporated onto the charge generation layer to form a 60nm organic film layer;

[0123] 7: Second light-emitting unit, compound H1 and compound D1 are co-deposited on the second hole transport layer to form an organic film layer of 20 nm, with a volume ratio of (98:2);

[0124] 8: The second electron transport layer, compound ET and Liq are co-deposited on the light-emitting layer to form a 30nm organic film layer, with a volume ratio of (50:50);

[0125] 9: Electron injection layer, Yb metal film layer after evaporation of 10nm.

[0126] 10: Cathode, 120nm of aluminum is evaporated as the cathode.

[0127] The manufacturing methods of device embodiments 2, 3, 4, 5, 6 and comparative example 1 are the same as those of device embodiment 1, except that the main compounds selected for the charge generation layers of device embodiments 2, 3, 4, 5, 6 are compounds H32, H37, H24, H26, H30, respectively, and the main compound selected for device comparative example 1 is E1.

[0128] The structures of the compounds used in the device are shown below:

[0129]

[0130] After the OLED device is prepared, the OLED device is characterized by standard methods to measure the voltage (V), current efficiency (cd / A) and lifespan. The driving voltage, current efficiency and lifespan are all based on the current density J = 10 mA / cm 2 The measured values ​​under are summarized in Table 1, and the test data of various OLEDs are summarized in Table 1.

[0131] Table 1

[0132] Device Characterization Driving voltage(v) Current efficiency (cd / A) Lifespan (hrs) Device Example 1 3.7 46 550 Device Example 2 3.5 41 572 Device Example 3 3.6 37 585 Device Example 4 3.7 54 456 Device Example 5 3.2 32 444 Device Example 6 3.1 42 478 Comparative Example 1 4.6 23 376

[0133] By comparing the examples and comparative examples, it can be explained that, as shown in Table 1, the organic electroluminescent device including the specific compound combination according to the present disclosure as the CGL material has a reduced driving voltage and improved efficiency and a longer lifespan than the organic electroluminescent device of the comparative substance.

[0134] The above embodiments are only used to help understand the method and core idea of ​​the present invention. It should be noted that, for those skilled in the art, several improvements and modifications can be made to the present invention without departing from the principles of the present invention, and these improvements and modifications also fall within the scope of protection of the claims of the present invention.

Claims

1. A benzophenanthroline compound, characterized in that It has the structure shown in formula I: Wherein, R1 is selected from hydrogen, deuterium, halogen, C1-C6 straight chain or branched alkyl; m is any integer from 1 to 3; Ar1 and Ar2 are independently selected from phenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl or triazinyl; L is selected from pyridylene, substituted or unsubstituted phenylene; The phenylene group may be further substituted by a C1-C6 straight or branched alkyl group; A has the structure shown in formula II: R2 is selected from hydrogen, deuterium, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclobutyl, phenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, naphthyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, fluorenyl, carbazolyl, dibenzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl or benzotriazolyl; n is 1; Indicates the connection location.

2. The benzophenanthroline compound according to claim 1, characterized in that The R2 is selected from hydrogen, deuterium, naphthyl, dibenzofuranyl, N-methylbenzimidazolyl or N-ethylbenzimidazolyl.

3. The benzophenanthroline compound according to claim 1, characterized in that Has any of the following structures:

4. An organic light-emitting device, comprising an anode, a cathode, a first stack and a second stack located between the anode and the cathode, and at least one charge generation layer located between the first stack and the second stack, wherein the charge generation layer contains at least one benzophenanthroline compound according to any one of claims 1 to 3.

5. An organic light-emitting device, comprising an anode, a cathode, a first stack and a second stack located between the anode and the cathode, and at least one electron blocking layer located between the first stack and the second stack, wherein the electron blocking layer contains at least one benzophenanthroline compound according to any one of claims 1 to 3.

6. An organic light-emitting device, comprising an anode, a cathode, a first stack and a second stack located between the anode and the cathode, and at least one electron transport layer located between the first stack and the second stack, wherein the electron transport layer contains at least one benzophenanthroline compound according to any one of claims 1 to 3.

7. A display panel comprising the organic light emitting device according to any one of claims 4 to 6.

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