Organic compound, OLED (Organic Light Emitting Diode) with compound and organic light emitting device

Abstract

The invention relates to the technical field of preparation of organic photoelectric materials, in particular to an organic compound, an OLED with the compound and an organic light-emitting device with the compound. According to the general formula compound provided by the invention, by utilizing the combination of the diphenyl heterocyclic ring and the substituted continuous three-ortho-position connected benzene, the transmission of charges and the stability of molecules are facilitated, the steric hindrance of the molecules can be increased, and the molecules are prevented from being crystallized at high temperature due to excessive planarization. Due to the structural characteristics in the two aspects, the whole molecule shows good hole injection and migration performance. When the compound provided by the invention is used as a light-emitting auxiliary layer material in the organic electroluminescent device, the efficiency roll-off of the device can be inhibited, and the hole injection and migration efficiency in the device can be effectively improved, so that the device is ensured to obtain an excellent effect of low starting voltage, and the service life of the device is prolonged. The preparation process of the compound is simple and easy to implement, raw materials are easy to obtain, and the compound is suitable for mass production and amplification and has a good industrialization prospect.

Description

Technical Field

[0001] The invention relates to the technical field of preparation of organic photoelectric materials, and in particular to an organic compound, an OLED having the compound, and an organic light-emitting device. Background Art

[0002] Organic light-emitting diodes (OLEDs), also known as organic electroluminescent devices, are a technology that allows organic materials to emit light through carrier injection and recombination under the action of an electric field. It can convert electrical energy into light energy through organic light-emitting materials. OLED is essentially a thin-film stacking device. In theory, when both the anode and the cathode are transparent electrodes, the light emitted by the light-emitting layer can be transmitted from the anode to the outside of the device and from the cathode to the outside of the device. Therefore, according to the different paths of light transmission, devices can be divided into bottom-emitting devices and top-emitting devices. The light of the bottom-emitting device is transmitted from the anode to the outside of the device through the substrate, and the light of the top-emitting device is transmitted to the outside of the device through the cathode. The light emission direction of the top-emitting device is on the cathode side, without passing through the substrate, and the image is more delicate and clear, and the color is also higher. However, in the structure of the top-emitting organic electroluminescent device, the brightness and color observed at different viewing angles will be very different, which seriously affects the product performance.

[0003] At present, OLED display technology still has the problems of high driving voltage and short display life, which seriously affect the further practical application of this technology. Therefore, it is necessary to continue to work hard to develop organic light-emitting devices with low voltage drive, high brightness and long life. Organic hole materials play an important role in transferring holes injected from the anode to the light-emitting layer. Hole transport materials with excellent hole mobility are beneficial to the injection balance of carriers in the device, thereby reducing the driving voltage of the device. On the other hand, in order to prevent the excitons generated in the light-emitting layer from diffusing to the hole transport layer, resulting in color cast and reduced luminous efficiency, the hole transport layer is also required to block the excitons from diffusing outward, prevent efficiency roll-off and improve the stability of the device.

[0004] In order to continuously improve the performance of OLED devices, it is necessary not only to innovate the structure and manufacturing process of OLED devices, but also to continuously research and innovate on OLED optoelectronic functional materials, create higher-performance OLED functional materials, and reasonably match them with existing materials to improve the luminous efficiency and service life of the device. Therefore, finding suitable OLED optoelectronic functional materials for OLED devices to solve the above problems is a long-term demand in the field. Summary of the invention

[0005] In view of the problems existing in the prior art, the present application provides an organic compound, an OLED having the compound, and an organic light-emitting device. The organic compound of the present invention is a luminescent material compound, which is particularly suitable for use in light-related devices or components. In particular, the organic compound of the present invention can be used as a luminescent auxiliary layer in the device or component to reduce the operating voltage of the light-emitting device and improve the luminous efficiency. In addition, using the compound of the present invention as a luminescent auxiliary layer and preparing a device or component together with a specific luminescent layer material compound can enable the device or component to exhibit a lower operating voltage, a higher BI luminous efficiency, and a longer service life.

[0006] The present invention provides a luminescent material compound, wherein the luminescent material compound has the following formula (I):

[0007] The structure shown:

[0008]

[0009] R 1 Each occurrence is independently selected from hydrogen, C1-C20 alkyl; R 2 Each occurrence is independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl; R 3 Each occurrence is independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, substituted or unsubstituted C6-C30 aryl, and R 1 -R 3 Each is independently a single substituent to the maximum possible number of substituents or no substituent;

[0010] R 3 is selected from hydrogen, deuterium, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl;

[0011] X is selected from O, S, CR 4 、SiR 5 R 6 NR 7 , CR 8 R 9 ; Among them, R 4 -R 9 Each is independently selected from hydrogen, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C3-C24 cycloalkyl, substituted or unsubstituted C6-C30 aryl; R 1 -R 9 At least one hydrogen may be replaced by deuterium; and L is selected from absent or C6-C30 non-fused ring aromatic group.

[0012] Optional, R3 Any one selected from the group consisting of hydrogen, deuterium, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, dimethylfluorenyl, tert-butyl-substituted dimethylfluorenyl, and N-phenylcarbazolyl.

[0013] Optionally, the R 1 -R 9 Each is independently a single substituent to the maximum possible number of substituents or no substituent, and any adjacent substituents are optionally joined or fused to form a ring.

[0014] Furthermore, in formula (I), the R 1 Each is independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl; R 2 Each is independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, triphenyl, alkoxy, alkylthio, and the group consisting of.

[0015] Optionally, the R 4 -R 9 Each is independently selected from hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, cyclopropane, cyclobutane, cyclopentyl, cyclohexane, phenyl, and the group consisting of.

[0016] L is selected from any one of a single bond, a phenyl group, a biphenyl group or a triphenyl group. 1 -R 9 At least one hydrogen may be replaced by deuterium.

[0017] According to one or more embodiments, the compound is selected from any one of the chemical structures shown below, wherein "D" represents deuterium:

[0018]

[0019]

[0020]

[0021]

[0022]

[0023]

[0024]

[0025]

[0026]

[0027]

[0028]

[0029] The present invention also provides a use of the organic compound described above in preparing an organic electroluminescent device.

[0030] The present invention also provides an organic electroluminescent device, which includes: a substrate layer; a first electrode, which is on the substrate; an organic light-emitting functional layer, which is on the first electrode; a second electrode, which is on the organic light-emitting functional layer; the organic light-emitting functional layer includes a hole transport layer, a light-emitting layer, and a light-emitting auxiliary layer located between the hole transport layer and the light-emitting layer; the light-emitting auxiliary layer includes an organic compound with a structure as shown in formula (I).

[0031] Optionally, the light-emitting layer of the organic electroluminescent device is selected from a light-emitting composition component, wherein the light-emitting composition component includes a compound having a structure represented by the following formula (III) and a compound having a structure represented by the following formula (IV); the compound having a structure represented by the following formula (III) and the compound having a structure represented by the following formula (IV) are combined in equal proportions in the light-emitting composition component;

[0032]

[0033] In formula (III), Q 1 -Q 2 are independently selected from hydrogen, deuterium, and C6-C30 aryl; in formula (IV), Q 3 -Q 4 Each is independently selected from hydrogen, deuterium, and C6-C30 aryl.

[0034] In some embodiments, Q 1 -Q 2 , Q 3 -Q 4 Each is independently selected from the group consisting of hydrogen, deuterium, phenyl, biphenyl, naphthyl, and the like.

[0035] Preferably, the compound with the structure represented by formula (III) and the compound with the structure represented by formula (IV) in the luminescent composition are combined in equal proportions.

[0036] In some embodiments, the compound represented by formula (III) is selected from any one of the following chemical structures:

[0037]

[0038] In some embodiments, the compound of the structure represented by formula (IV) is selected from any one of the following chemical structures, wherein "D" represents deuterium:

[0039]

[0040] Preferably, the device comprises one or more combinations of blue, green or red organic light-emitting material layers; different organic light-emitting material layers are stacked in a transverse or longitudinal manner.

[0041] The organic electroluminescent device of the present invention can be used in OLED lighting and display devices. Specifically, it can be used in the commercial field, such as display screens of products and equipment such as POS machines and ATM machines, copiers, vending machines, game machines, gas stations, card punching machines, access control systems, electronic scales, etc.; in the communication field, such as display screens of products such as mobile phones, various video intercom systems (videophones), mobile network terminals, ebooks (electronic books), etc.; in the computer field, such as display screens of home and / or commercial computers (PC / workstations, etc.), PDAs and laptops; in consumer electronic products, such as display screens of decorative items (soft screens) and lamps, various audio equipment, MP3, calculators, digital cameras, head-mounted displays, digital video cameras, portable DVDs, portable televisions, electronic clocks, handheld game consoles, various household appliances (OLED TVs), etc.; in the transportation field, such as various indicator and symbol display screens such as GPS, car audio, car phones, aircraft instruments and equipment.

[0042] Preferably, the organic electroluminescent device prepared by the present invention is used in smart phones, tablet computers, smart wearable devices, televisions, VR, micro-display fields, and automobile central control screens or automobile taillights.

[0043] The present invention also provides a display or lighting device, which comprises one or more of the organic electroluminescent devices described above.

[0044] Compared with the prior art, the present invention has the following beneficial effects:

[0045] The present invention is based on a combination of a diphenyl heterocyclic structure, a substituted or unsubstituted phenyl group connected in three consecutive ortho positions, and an aromatic group substituted with a tert-butyl group to form a new luminescent compound. It is not only conducive to the transfer of charges and the stability of the molecule, but also can increase the steric hindrance of the molecule, preventing the molecule from being excessively planarized and forming crystals at high temperatures. The specific substituent groups of the present invention enable the molecule as a whole to exhibit good hole injection and migration properties. When the compound of the present invention is used as a luminescent auxiliary layer material in an organic electroluminescent device, the efficiency roll-off of the device can be suppressed, and the hole injection and migration efficiency in the device can be effectively improved, thereby ensuring that the device obtains the excellent effect of a low starting voltage and prolonging the life of the device. The preparation process of the compound of the present invention is simple and easy, the raw materials are easily available, and it is suitable for mass production and amplification, and has good industrialization prospects. DETAILED DESCRIPTION

[0046] The technical solutions in conjunction with the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all the embodiments. Based on the embodiments in the present invention, all other embodiments obtained by those skilled in the art without making creative work are within the scope of protection of the present invention. Unless otherwise stated, all commercial reagents involved in the following tests are used directly after purchase.

[0047] The "C1-C24 alkyl" of the present invention refers to a monovalent alkyl group having 1 to 24 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms. Examples of the term include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-hexyl, etc.

[0048] The "C3-C24 cycloalkyl" of the present invention refers to a cycloalkyl having 3 to 24 carbon atoms and having a monocyclic or polycyclic condensed ring, which can be arbitrarily substituted by 1 to 3 alkyl groups. Such cycloalkyl includes, for example, monocyclic structures such as cyclopropyl, cyclobutyl, cyclopentyl, cyclooctyl, 1-methylcyclopropyl, 2-methylcyclopentyl, 2-methylcyclooctyl, etc., or polycyclic structures such as adamantyl, etc.

[0049] The "C6-C30 aryl" of the present invention refers to an unsaturated aromatic carbocyclic ring having 6-30 carbon atoms and having a monocyclic (such as phenyl) or polycyclic condensation (such as naphthyl or anthracenyl), preferably having 6-24 carbon atoms, more preferably 6-18 carbon atoms. Preferred aryl groups include phenyl, naphthyl, etc. Unless otherwise defined for individual substituents, such aryl groups may be optionally substituted by 1-3 of the following substituents: hydroxyl, acyl, acyloxy, alkyl, alkoxy, alkenyl, alkynyl, amino, aminoacyl, aryl, aryloxy, carboxyl, carboxyl ester, aminocarboxyl ester, cyano, halogen, nitro, heteroaryl, heterocycle, thioalkoxy, trihalomethyl, etc. Preferred substituents include alkyl, alkoxy, halogen, cyano, nitro, trihalomethyl and thioalkoxy. But not limited thereto.

[0050] The "substitution" mentioned in the present invention refers to mono-, di-, tri-, tetra- or penta-substitution, independently selected from deuterium, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, biphenyl or benzyl.

[0051] Throughout the specification, unless explicitly described to the contrary, "comprising" any component will be understood to imply the inclusion of other elements, rather than excluding any other elements. In addition, it should be understood that throughout the specification, when an element such as a layer, film, region or substrate is referred to as being "on" or "above" another element, it can be "directly on" another element, or there may be intervening elements. In addition, "on..." or "above..." means being located above the target portion, and does not necessarily mean being located above according to the direction of gravity.

[0052] An object of the present invention is to provide an organic electroluminescent device (OLED), which includes: a substrate layer; a first electrode, which is on the substrate; an organic light-emitting functional layer, which is on the first electrode; a second electrode, which is on the organic light-emitting functional layer; the organic light-emitting functional layer includes a hole transport layer, a light-emitting layer, and a light-emitting auxiliary layer located between the hole transport layer and the light-emitting layer; the light-emitting auxiliary layer includes an organic compound with a structure as shown in formula (I).

[0053] In a preferred embodiment of the present invention, the light-emitting layer contains a light-emitting composition compound, and the light-emitting composition includes a compound having a structure represented by formula (III) and a compound having a structure represented by formula (IV).

[0054] The substrate of the present invention can be any substrate used in typical organic light-emitting devices. It can be a glass or transparent plastic substrate, or a substrate of an opaque material such as silicon or stainless steel, or a flexible PI film. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and waterproofness. Depending on the properties of the substrate, the use direction is different. Other materials in the organic electroluminescent device can be selected from the known related materials used in OLED devices.

[0055] As a guest material capable of producing blue fluorescence, blue phosphorescence, green fluorescence, green phosphorescence and blue-green fluorescence, it is not only required to have an extremely high fluorescence quantum luminescence efficiency, but also to have an appropriate energy level that can effectively absorb the excitation energy of the host material to emit light. Such materials are not particularly limited.

[0056] Example 1: Compound P 1 Synthesis

[0057]

[0058] (1) Add P1-1 (10 mmol), P1-2 (25 mmol), sodium tert-butoxide (10 mmol), and 200 ml of toluene to the reaction flask. After nitrogen substitution, add pd2(dba)3 (5×10-2 mmoL), Sphos(5×10 -2 100 mL of n-heptane was added after the mixture was washed with water twice, and the mixture was slurried after the toluene was concentrated. The intermediate product P1-3 was obtained.

[0059] (2) P1-3 (10 mmol), P1-4 (25 mmol), sodium tert-butoxide (10 mmol), and 200 ml of toluene were added to the reaction flask. After nitrogen replacement, PD2(DBA)3 (5 × 10 -2 mmoL), Sphos(5×10 -2 mmoL), heated to 100-120°C, refluxed for 6 hours, and then stopped. Cooled to 30-40°C, added 200mL of water, and separated into layers. After washing with water twice, concentrated toluene, added 100mL of n-heptane, and slurried. The target product P1 was obtained.

[0060] The structure of the test target product P1 was obtained by liquid chromatography-mass spectrometry analysis: LC-MS (m / z) (Μ+): the theoretical value was 645.34, and the test value was 645.52.

[0061] Example 2: Compound P 3 Synthesis

[0062]

[0063] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 3 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 659.36, and the test value was 659.54.

[0064] Example 3: Compound P 23 Synthesis

[0065] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 23 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 813.38, and the test value was 813.57.

[0066] Example 4: Compound P 25 Synthesis

[0067]

[0068] (1) Add P25-1 (10 mmol), P25-2 (25 mmol), sodium tert-butoxide (10 mmol), and 200 ml of toluene to a reaction flask. After nitrogen substitution, add pd2(dba)3 (5×10-2 mmol) and Sphos (5×10-2 mmol), heat to 100-120°C, reflux for 6 hours, and stop the reaction. Cool to 30-40°C, add 200 ml of water, and separate the layers. After washing with water twice, concentrate the toluene, add 100 ml of n-heptane, and slurry. Obtain the intermediate product P25-3.

[0069] (2) Add P25-3 (10mmoL), P25-4 (25mmoL), sodium tert-butoxide (10mmoL), and 200ml of toluene to the reaction flask. After nitrogen replacement, add pd2(dba)3 (5×10-2mmoL) and Sphos (5×10-2mmoL), heat to 100-120°C, reflux for 6 hours, and stop the reaction. Cool to 30-40°C, add 200mL of water, and separate. After washing twice, add 100mL of n-heptane after concentrating toluene and beat. Obtain the target product P25. LC-MS (m / z) (M+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value is 769.37, and the test value is 769.57.

[0070] Example 5: Compound P 40 Synthesis

[0071]

[0072] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 40 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 783.39 and the test value was 783.60.

[0073] Example 6: Compound P 60 Synthesis

[0074]

[0075] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 60 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 823.42, and the test value was 823.63.

[0076] Example 7: Compound P 68 Synthesis

[0077] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 68, LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 761.40, and the test value was 761.71.

[0078] Example 8: Compound P 73 Synthesis

[0079]

[0080] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 73 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 619.29 and the test value was 619.50.

[0081] Example 9: Compound P 95 Synthesis

[0082] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 95 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 787.33, and the test value was 787.62.

[0083] Example 10: Compound P 97 Synthesis

[0084] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 97 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 694.33, and the test value was 694.54.

[0085] Example 11: Compound P 107 Synthesis

[0086] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 107 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 902.46, and the test value was 902.68.

[0087] Example 12: Compound P 109 Synthesis

[0088] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 109 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 721.37, and the test value was 721.56.

[0089] Example 13: Compound P 116 Synthesis

[0090] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 116 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 735.39 and the test value was 735.60.

[0091] Example 14: Compound P 119 Synthesis

[0092] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 119 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 873.43, and the test value was 873.72.

[0093] Example 15: Compound P 157 Synthesis

[0094] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 157 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 747.39, and the test value was 747.61.

[0095] Example 16: Compound P 181 Synthesis

[0096] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 181 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 695.32, and the test value was 695.54.

[0097] Example 17: Compound P 196 Synthesis

[0098] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 196 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 787.33, and the test value was 787.56.

[0099] Example 18: Compound P 217 Synthesis

[0100] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 217 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 660.43, and the test value was 660.62.

[0101] Example 19: Compound P 229 Synthesis

[0102] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 229 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 736.47 and the test value was 736.68.

[0103] Example 20: Compound P 230 Synthesis

[0104] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 1 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 753.50, and the test value was 753.72.

[0105] Example 21: Compound P 241 Synthesis

[0106] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 241 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 721.37, and the test value was 721.61.

[0107] Example 22: Compound P 243 Synthesis

[0108] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 243 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 771.39, and the test value was 771.70.

[0109] Example 23: Compound P 244 Synthesis

[0110] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 244 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 837.43, and the test value was 837.67.

[0111] Example 24: Compound P 245 Synthesis

[0112] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 245 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 837.43, and the test value was 837.63.

[0113] Example 25: Compound P 246 Synthesis

[0114] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 246 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 811.38, and the test value was 811.65.

[0115] Example 26: Compound P 247 Synthesis

[0116] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 247 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 827.36, and the test value was 827.59.

[0117] Example 27: Compound P 248 Synthesis

[0118] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 248 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 886.43, and the test value was 886.68.

[0119] Example 28: Compound P 251 Synthesis

[0120] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 251 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 811.42, and the test value was 811.63.

[0121] Example 29: Compound P 252 Synthesis

[0122] Compound P was synthesized according to the synthesis steps and reaction conditions of Example 1. 252 , LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 925.70 and the test value was 925.93.

[0123] Example 30: Synthesis of Compound H1-002

[0124]

[0125] (1) Add 3-bromo-9H-carbazole (10 mmol), H1-002-1 (10 mmol), and 10 mL of dioxane: water (4:1) to the reaction bottle, mix, place in a 50 mL flask, and reflux for 24 hours. Cool to room temperature, then slowly add saturated MgSO 4The solution was extracted with aqueous solution and ethyl acetate three times, and then the organic layer was subjected to a rotary evaporator to remove the solvent, and the intermediate product H1-002-2 was obtained by column chromatography.

[0126] (2) Add H1-002-2 (10 mmol), H1-002-3 (25 mmol), sodium tert-butoxide (10 mmol), and 200 mL of toluene to the reaction flask. After nitrogen replacement, add pd 2 (dba) 3 (5×10 -2 mmoL), Sphos(5×10 -2 100-200 mL of 1% ethyl acetate was added to the mixture, and the mixture was heated to 100-120°C, refluxed for 6 hours, and the reaction was stopped. The mixture was cooled to 30-40°C, 200 mL of water was added, and the mixture was separated into layers. After washing with water twice, 100 mL of n-heptane was added after concentrating the toluene, and the mixture was slurried to obtain the target product H1-002.

[0127] The structure of the test target product H1-002: LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 712.29, and the test value was 712.48.

[0128] Example 31: Synthesis of Compound H1-013

[0129]

[0130] (1) Add 3-bromo-9H-carbazole (10 mmol), H1-013-1 (10 mmol), and 10 mL of dioxane: water (4:1) to the reaction bottle, mix, place in a 50 mL flask, and reflux for 24 hours. Cool to room temperature, and then slowly add saturated MgSO 4 The solution was extracted with aqueous solution and ethyl acetate three times, and then the organic layer was subjected to a rotary evaporator to remove the solvent, and column chromatography was performed to obtain the intermediate product H1-013-2.

[0131] (2) H1-013-2 (10 mmol), H1-013-3 (25 mmol), sodium tert-butoxide (10 mmol), and 200 mL of toluene were added to the reaction flask. After nitrogen replacement, pd2(dba)3 (5×10 -2 mmoL), Sphos(5×10 -2 mmoL), heated to 100-120°C, refluxed for 6 hours, and stopped the reaction. Cooled to 30-40°C, added 200mL of water, and separated into layers. After washing with water twice, concentrated toluene, added 100mL of n-heptane, and slurried. The target product H1-013 was obtained.

[0132] The structure of the test target product H1-013: LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value is 788.32, and the test value is 788.53.

[0133] Example 32: Synthesis of Compound H2-003

[0134]

[0135] H2-003-1 (10 mmol), H2-003-2 (25 mmol), sodium tert-butoxide (10 mmol), and 200 mL of toluene were added to the reaction flask. After nitrogen replacement, pd 2 (dba) 3 (5×10 -2 mmoL), Sphos(5×10 -2 mmoL), heated to 100-120°C, refluxed for 6 hours, and stopped the reaction. Cooled to 30-40°C, added 200mL of water, and layered. After washing twice with water, 100mL of n-heptane was added after concentrating the toluene, and slurried. The target product H2-003 was obtained. The structure of the target product H2-003 was tested: LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 793.30, and the test value was 793.52.

[0136] Example 33: Synthesis of Compound H2-005

[0137]

[0138] H2-005-1 (10 mmol), H2-005-2 (25 mmol), sodium tert-butoxide (10 mmol), and 200 mL of toluene were added to the reaction flask. After nitrogen replacement, pd 2 (dba) 3 (5×10 -2 mmoL), Sphos(5×10 -2 mmoL), heated to 100-120°C, refluxed for 6 hours, and stopped the reaction. Cooled to 30-40°C, added 200mL of water, and layered. After washing twice with water, concentrated toluene, added 100mL of n-heptane, and slurried. Obtained the target product H2-005. Test the structure of the target product H2-005: LC-MS (m / z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 793.30, and the test value was 793.52.

[0139] Several examples of the application of the organic compounds of the present invention in OLED devices are listed below to further illustrate the beneficial effects of the compounds of the present invention. The materials used in the examples are purchased commercially or synthesized by themselves:

[0140] Device embodiment: structure and manufacturing method of application example 1:

[0141] First, use an ultrasonic cleaner to wash the alkali-free glass substrate with isopropanol for 15 minutes, and then perform UV ozone cleaning in the air for 30 minutes. The treated substrate is first evaporated with ITO / Ag / ITO 100nm as the anode by vacuum evaporation, and then the hole injection layer (HT:PD, 10nm), hole transport layer (NPB, 30nm), blue light-emitting layer (main ADN and doped BD (weight ratio 97:3, 30nm), electron transport layer (compound B-012:Liq=1:1, 30nm), electron injection layer (LiF, 0.5nm) are deposited in sequence, and Mg and Ag (weight ratio 10:1, 15nm) are co-evaporated to make a semi-transparent cathode, and then compound A-006 (65nm) is evaporated as a covering layer. Finally, the light-emitting device is encapsulated with epoxy resin adhesive in a nitrogen atmosphere, which is recorded as Application Example 1. The molecular structure formula of the relevant materials is as follows:

[0142] Fabrication of OLED devices:

[0143] As a reference preparation method for a device embodiment, the present invention evaporates 50-500nm ITO / Ag / ITO on an alkali-free glass substrate as an anode, evaporates a hole injection layer (10nm-50nm), a hole transport layer (50-120nm), a light-emitting auxiliary material (50-200nm), a light-emitting layer, an electron transport layer (30-100nm), and an electron injection layer (1-10nm) on the anode in sequence, and then co-evaporates Mg and Ag (weight ratio 10:1, 10-50nm) to make a semi-transparent cathode, and then evaporates a cover layer compound. Finally, the light-emitting device is encapsulated using an epoxy resin adhesive in a nitrogen atmosphere.

[0144] In a preferred embodiment, the structure of the light-emitting device provided by the present invention is as follows: first, an alkali-free glass substrate is washed with isopropyl alcohol using an ultrasonic cleaner for 15 minutes, and then a UV ozone cleaning treatment is performed in air for 30 minutes. The treated substrate is firstly evaporated with ITO / Ag / ITO 100nm as an anode by vacuum evaporation, and then a hole injection layer (HT:PD, 10nm), a hole transport layer (HT, 120nm), and a light-emitting auxiliary material (compound P) are evaporated on the anode. 1, 50nm), light-emitting layer (compound H1-002:H2-003 (50:50), 27nm, and doping material GD, 3nm), electron transport layer (ET:Liq (50:50), 30nm), electron injection layer (Yb, 1nm) are sequentially stacked and evaporated, and Mg and Ag (weight ratio 10:1, 15nm) are co-evaporated to make a semi-transparent cathode, and then compound CPL (65nm) is evaporated as a covering layer. Finally, the light-emitting device is encapsulated with epoxy resin adhesive in a nitrogen atmosphere, which is recorded as Application Example 1. The molecular structure formula of the relevant materials is as follows:

[0145]

[0146] Device structure Application Example 1-Application Example 45, Comparative Example 1-Comparative Example 7 preparation: The device structure and preparation method are similar to those of Application Example 1, except that the main material of the light-emitting layer and the auxiliary material of the light-emitting layer of the OLED device are respectively prepared using the compounds listed in Table 1, and the prepared light-emitting devices are respectively recorded as Application Example 1-Application Example 45 and Comparative Example 1-Comparative Example 7. The molecular structure formula of the relevant comparative example materials is as follows:

[0147]

[0148] Table 1. Organic electroluminescent devices and electronic luminescence characteristics

[0149]

[0150]

[0151]

[0152] It can be seen from the test data in Table 1 that Application Examples 1 to Application Examples 45 have lower operating voltage, higher BI luminous efficiency and longer service life than Comparative Examples 1 to 4. In addition, the electronic device prepared after adjusting the main material still maintains stable luminous performance, and has outstanding performance improvements in operating voltage, BI luminous efficiency and service life compared to each comparative example. It can be seen that the improvement in the performance of each application example is based on the luminescent auxiliary material of the present invention, as well as the better matching of the main material and the luminescent auxiliary material, thereby improving the balance and recombination probability of electrons and holes, effectively improving the conversion rate of excitons, and improving device performance.

[0153] The above shows and describes the basic principles, main features and advantages of the present invention. Those skilled in the art should understand that the present invention is not limited to the above embodiments. The above embodiments and descriptions are only for explaining the principles of the present invention. The present invention may be subject to various changes and improvements without departing from the spirit and scope of the present invention. These changes and improvements fall within the scope of the present invention. The scope of protection of the present invention is defined by the attached claims and their equivalents.

Claims

1. A luminescent material compound, characterized in that: The compound has a structure shown in the following formula (I): In formula (I), each occurrence of R1 is independently selected from hydrogen, C1-C20 alkyl; each occurrence of R2 is independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl; each occurrence of R3 is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, substituted or unsubstituted C6-C30 aryl and the group consisting of; R1-R3 are independently a single substituent to the maximum possible number of substituents or no substituent; R3 is selected from hydrogen, deuterium, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl; X is selected from O, S, CR4, SiR5R6, NR7, CR8R9; Among them, R4-R9 are each independently selected from hydrogen, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C3-C24 cycloalkyl, substituted or unsubstituted C6-C30 aryl; at least one hydrogen of R1-R9 can be replaced by deuterium; L is selected from a single bond or a C6-C30 non-condensed ring aromatic group.

2. A compound according to claim 1, characterized in that R3 is selected from any one of hydrogen, deuterium, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, dimethylfluorenyl, tert-butyl-substituted dimethylfluorenyl, or N-phenylcarbazolyl.

3. A compound according to claim 1, characterized in that The R1 is independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl, and tert-butyl; and R2 is independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, and biphenyl.

4. A compound according to claim 1, characterized in that The R4-R9 are each independently selected from hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, cyclopropane, cyclobutane, cyclopentyl, cyclohexane, and phenyl.

5. A compound according to claim 1, characterized in that L is selected from any one of a single bond, a phenyl group, a biphenyl group, and a triphenyl group.

6. A compound according to claim 1, characterized in that The compound is selected from any one of the following chemical structures, wherein "D" represents deuterium:

7. Use of the organic compound according to any one of claims 1 to 6 in the preparation of an organic electroluminescent device.

8. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises: a substrate layer; a first electrode, which is on the substrate; an organic light-emitting functional layer, which is on the first electrode; a second electrode, which is on the organic light-emitting functional layer; the organic light-emitting functional layer comprises a hole transport layer, a light-emitting layer, and a light-emitting auxiliary layer located between the hole transport layer and the light-emitting layer; the light-emitting auxiliary layer comprises the organic compound as described in any one of claims 1 to 6.

9. The organic electroluminescent device according to claim 8, characterized in that: The light-emitting layer comprises a light-emitting composition, and the light-emitting composition comprises a compound having a structure represented by the following formula (III) and a compound having a structure represented by the following formula (IV); In formula (III), Q1-Q2 are each independently selected from hydrogen, deuterium, and a C6-C30 aryl group; in formula (IV), Q3-Q4 are each independently selected from hydrogen, deuterium, and a C6-C30 aryl group.

10. The organic electroluminescent device according to claim 9, characterized in that: Q1-Q2, Q3-Q4 are each independently selected from hydrogen, deuterium, phenyl, biphenyl, and naphthyl.

11. The organic electroluminescent device according to claim 9, characterized in that: The luminescent composition comprises a compound having a structure represented by formula (III) and a compound having a structure represented by formula (IV) in an equal proportion.

12. The organic electroluminescent device according to claim 9, characterized in that: The compound represented by formula (III) is selected from any one of the following chemical structures:

13. The organic electroluminescent device according to claim 9, characterized in that: The compound of the structure represented by formula (IV) is selected from any one of the following chemical structures, wherein "D" represents deuterium:

14. Use of the organic electroluminescent device according to any one of claims 8 to 13 in a display or lighting device.

15. A display or lighting device, characterized in that: The device comprises the organic electroluminescent device according to any one of claims 8 to 13.

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