An organic condensed ring compound and its preparation method and application

Abstract

The present invention discloses an organic condensed ring compound and a preparation method and application thereof, belonging to the field of organic photoelectric materials. The general structural formula of the organic condensed ring compound is: #imgabs0# wherein R 1 represents no substitution, a monosubstituted group, a disubstituted group or a trisubstituted group; R 2 and R 3 R independently represents no substitution, a mono-substituent or a di-substituent; 4 represents unsubstituted, monosubstituted, disubstituted, trisubstituted, tetrasubstituted or pentasubstituted; Ar 1 Represents a single substituent; R 1 , R 2 , R 3 , R 4 Each independently is at least one of a substituted or unsubstituted C1-C8 alkyl, a substituted or unsubstituted C3-C15 cycloalkyl, a substituted or unsubstituted C6-C18 aryl, and a substituted or unsubstituted C4-C12 aromatic heterocyclic group. The organic condensed ring compound can be combined with a specific second host material as an organic light-emitting host material to prepare an organic electroluminescent device with high luminous efficiency, low driving voltage, and long life.

Description

Technical Field

[0001] The invention relates to the field of organic photoelectric materials, in particular to an organic condensed ring compound and a preparation method and application thereof. Background Art

[0002] Optoelectronic devices made of organic materials are increasingly in demand due to their many advantages; among them, since many materials used to make such devices are relatively cheap, organic optoelectronic devices have an advantage over inorganic devices in terms of cost. In addition, the inherent properties of organic materials, such as flexibility, make them very suitable for special applications, such as manufacturing on flexible substrates.

[0003] Organic optoelectronic devices include organic light-emitting devices, organic photosensitive transistors, organic photovoltaic cells, and organic photodetectors. For organic light-emitting devices, the performance of organic materials can be more advantageous than conventional materials. For example, the wavelength of light emitted by the organic emission layer can generally be easily adjusted with a suitable dopant. When a voltage is applied to the device, the organic film will emit light. Organic light-emitting devices can also be used in flat panel displays, lighting, and backlighting. Therefore, organic light-emitting devices have been widely studied, developed, and used in various fields.

[0004] At present, the materials of organic light-emitting devices mainly have technical problems such as short lifespan, low luminous efficiency and power efficiency, and high driving voltage, which increase the cost of using such materials and pose great obstacles to the development of the market in the future.

[0005] Therefore, developing a new organic condensed ring compound to prepare an organic electroluminescent device with low driving voltage, high luminous efficiency and long service life is a technical problem that needs to be solved urgently by people in this field. Summary of the invention

[0006] The purpose of the embodiments of the present invention is to provide an organic condensed ring compound to solve the problems raised in the above background technology.

[0007] To achieve the above objectives, the embodiments of the present invention provide the following technical solutions:

[0008] An organic condensed ring compound, the general structural formula of which is Formula C:

[0009]

[0010] In the formula, R1 represents unsubstituted, monosubstituted, disubstituted or trisubstituted; R2 and R3 independently represent unsubstituted, monosubstituted or disubstituted; R4 represents unsubstituted, monosubstituted, disubstituted, trisubstituted, tetrasubstituted or pentasubstituted; Ar1 ​​represents a monosubstituted group; R1, R2, R3, R4 are each independently at least one of substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C4-C12 aromatic heterocyclic group; Ar1 ​​is any one of the following substituents:

[0011] substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di(C1-C30)alkylamino, substituted or unsubstituted mono- or di(C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, *-L1-NAr 11 Ar 12 , *-Ar 21 -(L2-Ar 22 ) a ; * indicates the connection site;

[0012] L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; and Ar 11 and Ar 12 Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; Ar 21 represents a substituted or unsubstituted nitrogen-containing (3- to 20-membered) heteroaryl group; L2 represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3- to 30-membered) heteroarylene group; Ar 22represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl group, a substituted or unsubstituted condensed ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted tri(C1-C30) alkylsilyl group, a substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl group, a substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl group, or a substituted or unsubstituted tri(C6-C30) arylsilyl group; a represents 1 or 2; and when a represents 2, each -(L2-Ar 22 ) can be the same or different.

[0013] Preferably, the C1-C8 alkyl group is a C1-C8 straight chain alkyl group or a branched alkyl group; the C3-C15 cycloalkyl group is any one of a monocyclic alkyl group, a polycyclic alkyl group, and a spiroalkyl group, and the carbon atoms on the substituted C3-C15 cycloalkyl group may be substituted by at least one heteroatom; the heteroatom is at least one of N, O, S, Si, Se, and Ge; the C6-C18 aromatic group is a monocyclic group or a polycyclic group; the polycyclic group has multiple rings in which two carbon atoms are shared by two adjacent rings, at least one of which is an aromatic ring, and the other rings are at least one of a cycloalkyl group, a cycloalkenyl group, an aromatic group, and a heteroaryl group; the C4-C12 aromatic heterocyclic group is any one of furan, thiophene, and pyridine.

[0014] Preferably, the C1-C8 alkyl group is any one of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl; the C3-C15 cycloalkyl group is any one of cyclopropyl, cyclopentyl, cyclohexyl and adamantyl; the heteroatom is at least one of N, O and S; the C6-C18 aryl group is any one of benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene and pyrene.

[0015] It should be noted that the above-mentioned "substitution" means that the hydrogen atom bonded to the carbon atom of the compound is changed into another substituent, and the position of substitution is not limited, as long as the position is the position where the hydrogen atom is substituted, that is, the position that the substituent can replace, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0016] In addition, the term "substituted or unsubstituted" means substituted by deuterium, a halogen group, a nitrile group, a hydroxyl group, a carbonyl group, an ester group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group, an alkylamine group, a heterocyclylamine group, an arylamine group, an aryl group, a heterocyclyl group or the like, or by a substituent in which two or more of the substituents shown above are connected, or by having no substituent.

[0017] Preferably, the structural formula of the organic condensed ring compound is any one of the following structural formulas:

[0018]

[0019]

[0020]

[0021]

[0022]

[0023]

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030] Only some specific structural forms are listed above, but this series of compounds is not limited to the above molecular structures. Any simple transformation of some simple groups and their substituted groups and substitution positions can obtain other specific molecular structures, which will not be described one by one here.

[0031] Another object of the present invention is to provide a method for preparing the above-mentioned organic condensed ring compound, the synthesis route of which is:

[0032]

[0033] R1, R2, R3, R4, Ar1 are the same as the above ranges; the preparation method of the organic condensed ring compound comprises the following steps:

[0034] Under the protection of inert gas, compound A with the general formula A, compound B with the general formula B and an alkaline substance are added to a solvent, and a catalyst is added to carry out heating reaction to obtain the organic condensed ring compound.

[0035] The specific steps may include:

[0036] Under the protection of inert gas, compound A with the general formula A, compound B with the general formula B, and an alkaline substance are added to a mixed solvent of toluene, ethanol, and water, and a catalyst is added to carry out heating reaction. After the reaction is completed, suction filtration, washing, drying, column chromatography, rotary evaporation and other operations are performed to obtain compound C (that is, the above-mentioned organic condensed ring compound).

[0037] Furthermore, when there is an amino group in Ar1, -B(OH)2 can be omitted;

[0038] The inert gas in the above steps is nitrogen or argon;

[0039] The catalyst selected was tetrakis(triphenylphosphine)palladium;

[0040] The alkaline substance is potassium carbonate or sodium carbonate, preferably potassium carbonate;

[0041] The molar ratio of compound A to potassium carbonate is 1:(1.1-2), preferably 1:1.5;

[0042] The molar ratio of compound A to compound B is 1:(1.1-1.5), preferably 1:1.2;

[0043] The molar ratio of tetrakis(triphenylphosphine)palladium to compound A is (0.005-0.05):1, preferably 0.01:1;

[0044] The heating reaction temperature is 70-110°C and the reaction time is 20-30h;

[0045] The volume ratio of toluene / ethanol to water in the solvent is 2:1:1;

[0046] The ratio of compound A to solvent is 50 mmol: (350-400) mL;

[0047] The detergent used for washing is one or a mixture of water, anhydrous ethanol, petroleum ether;

[0048] The drying temperature is 70-80℃ and the drying time is more than 8h;

[0049] The column chromatography used a mixture of dichloromethane and petroleum ether as solvent and silica gel column chromatography.

[0050] Another object of the embodiment of the present invention is to provide a use of the above organic condensed ring compound in the preparation of an organic electroluminescent device.

[0051] Another object of an embodiment of the present invention is to provide an organic light-emitting host material that partially or entirely contains the above-mentioned organic condensed ring compound.

[0052] Preferably, the organic light-emitting host material includes a first host material and a second host material; the first host material is the organic condensed ring compound; the structural formula of the second host material is any one of the following structural formulas:

[0053]

[0054]

[0055]

[0056]

[0057]

[0058] Preferably, the weight ratio of the first host material to the second host material is 1:99-99:1; preferably 10:90 to 90:10, more preferably 30:70 to 70:30, even more preferably 40:60 to 60:40, and still more preferably 50:50.

[0059] Another object of an embodiment of the present invention is to provide an organic electroluminescent device, comprising an anode, a cathode and at least one intermediate layer arranged between the anode and the cathode, wherein the intermediate layer comprises a light-emitting layer, characterized in that the light-emitting layer partially or completely contains the above-mentioned organic light-emitting host material.

[0060] Further, the anode is selected from indium tin oxide, tin oxide, zinc oxide or indium oxide, and the thickness of the anode is 10 to 500 nm; the cathode is selected from Al, Li, Na, K, Mg, Ca, Au, Ag or Pb, and the thickness of the cathode is 100 to 1000 nm. Further, the light-emitting layer also includes a doping material, and the mass ratio of the organic light-emitting main material to the doping material is (90 to 99.5): (0.5 to 10); the thickness of the light-emitting layer is 10 to 500 nm. Further, the intermediate layer also includes a functional layer; the functional layer is one or more of a hole injection layer, a hole transport layer, a hole injection-hole transport functional layer, an electron blocking layer (EBL), a hole blocking layer, an electron transport layer, an electron injection layer, and an electron transport-electron injection functional layer.

[0061] Compared with the prior art, the beneficial effect of the embodiments of the present invention is that an organic condensed ring compound provided by the embodiments of the present invention can be combined with a specific second main material as an organic light-emitting main material to prepare an organic electroluminescent device with high luminous efficiency, low driving voltage and long life characteristics. DETAILED DESCRIPTION

[0062] The following will be combined with the embodiments of the present invention to clearly and completely describe the technical solutions in the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. The present invention takes the following organic condensed ring compounds as examples, and the preparation methods of other organic condensed ring compounds are similar, which will not be given separately here.

[0063] The preparation route of compound A used in the following examples is as follows:

[0064]

[0065] Specifically, the synthesis method of compound A comprises the following steps:

[0066] S1. Preparation of compound A-1: ​​Add compound 7-bromo-2-phenyl-benzoxazole (203 mmol) (CAS No.: 1642542-08-2), 5-chloro-2-formylphenylboronic acid (CAS No.: 870238-36-1) (203 mmol), tetrakis(triphenylphosphine)palladium (10 mmol), sodium carbonate (507 mmol), toluene (800 mL), ethanol (200 mL), and distilled water (200 mL) to a reaction vessel, and reflux and stir at 100°C for 5 hours. A precipitate is precipitated, and the precipitate is filtered, washed with water, anhydrous ethanol, and petroleum ether in sequence, and then dried, and then silica gel column chromatography is performed using dichloromethane as solvent, and the filtrate is concentrated to solid precipitation to obtain intermediate A-1 (63.7 mmol, yield: 31.4%). Mass spectrometry test: theoretical value is 408.89; test value is 408.10.

[0067] S2, preparation of compound A-2: After introducing compound A-1 (63.7mmol), (methoxymethyl) triphenylphosphonium chloride (95.28mmol) and tetrahydrofuran (800mL) into the reaction vessel, the reaction mixture was stirred for 15 minutes, cooled to a system temperature of 0°C, and potassium tert-butoxide (1M in THF, 120mL) was slowly added dropwise thereto. The mixture was slowly heated to 25°C, and then stirred for another 5 hours. 120ml of distilled water was added, and the system was extracted three times with 240mL of dichloromethane. The organic phase was spin-dried, and then dichloromethane was used as a solvent, and silica gel column chromatography was performed, and the filtrate was concentrated to solid precipitation to obtain intermediate A-2 (34.3mmol, yield: 54%). Mass spectrometry test: The theoretical value is 436.94; the test value is 436.13.

[0068] S3, preparation of compound A: After introducing compound A-2 (34.3mmol), Eaton's reagent (1.5mL) and chlorobenzene (620mL) into a reaction vessel, the mixture was stirred under reflux for 3 hours. After the reaction was completed, the mixture was cooled to room temperature and then extracted with dichloromethane. The organic phase was spin-dried, and then dichloromethane was used as a solvent for silica gel column chromatography. The filtrate was concentrated to solid precipitation to obtain product A (11g, yield: 79%). Mass spectrometry test: The theoretical value is 404.90; the test value is 436.11.

[0069] 1H NMR (500MHz, Chloroform-d)δ

[0070] (1H,8.76-8.73)(2H,8.22-8.17)(3H,7.97-7.94)(1H,7.78-7.76)(1H,7.69-7.61)(9H,7.51-7.31);

[0071] It can be seen from the above test results that this method can prepare high-purity compound A.

[0072] After a sufficient amount of compound A is prepared according to the above method, the preparation of the final product, an organic condensed ring compound, is started.

[0073] Example 1: Preparation of organic condensed ring compound C-1-005

[0074] Under nitrogen protection system, compound A (24.7mmol), B-1-005 (29.64mmol) (CAS No.: 103986-53-4), potassium carbonate (37.05mmol) were weighed and put into the reaction system, and a mixed solution of 200mL toluene, 100mL ethanol and 100mL pure water was added. Tetrakis(triphenylphosphine)palladium (0.025mmol) was added under nitrogen protection, and the mixture was heated under reflux at 100°C for 36 hours under nitrogen protection. After that, the mixture was cooled to 25°C, and a precipitate was precipitated. The precipitate was filtered, washed with water, anhydrous ethanol and petroleum ether in sequence, and then dried. Then, dichloromethane was used as solvent, and silica gel column chromatography was performed. The filtrate was concentrated to solid precipitation to obtain an organic condensed ring compound C-1-005 (6.91g, yield 54.79%) in the form of yellow powder.

[0075] Among them, the conditions for silica gel column chromatography are: dichloromethane and petroleum ether are selected as solvents, 600g of silica gel (200-300 mesh) is weighed as the adsorbent, petroleum ether is added and stirred until uniform, and then poured into the column, after the silica gel is settled, the mixture is added, the developing agent ratio is dichloromethane: petroleum ether = 1:7, and the eluent is used for purification.

[0076] The reaction route of the above preparation process is as follows:

[0077]

[0078] The obtained organic condensed ring compound C-1-005 was tested and analyzed, and the results are as follows:

[0079] HPLC purity: >99%.

[0080] Mass spectrometry test: theoretical value is 510.64; tested value is 510.21.

[0081] Elemental Analysis:

[0082] The calculated values ​​are: C: 89.38%; H: 5.13%; N: 5.49%;

[0083] The test values ​​are: C: 89.39%; H: 5.13%; N: 5.50%;

[0084] 1 H NMR (500 MHz, Chloroform-d)δ

[0085] (1H,9.57-9.56)(1H,8.32-8.30)(2H,8.21-8.19)(2H,7.99-7.93)(1H,7.86-7.8 4)(3H,7.79-7.74)(1H,7.65-7.63)(11H,7.51-7.36)(1H,7.32-7.31)(3H,7.26)

[0086] It can be seen from the above test results that Example 1 prepared a high-purity compound of the C-1-005 structure.

[0087] Example 2: Preparation of organic condensed ring compound C-1-074

[0088] Under nitrogen protection system, compound A (24.7mmol), B-1-074 (29.64mmol) (CAS No.: 480424-61-1), potassium carbonate (37.05mmol) were weighed and put into the reaction system, and a mixed solution of 200mL toluene, 100mL ethanol and 100mL pure water was added. Tetrakis(triphenylphosphine)palladium (0.025mmol) was added under nitrogen protection, and the mixture was heated under reflux at 100°C for 36 hours under nitrogen protection. After that, the mixture was cooled to 25°C, and a precipitate was precipitated. The precipitate was filtered, washed with water, anhydrous ethanol and petroleum ether in turn, and then dried. Then, dichloromethane was used as solvent, and silica gel column chromatography was performed. The filtrate was concentrated to solid precipitation to obtain an organic condensed ring compound C-1-074 (7.23g, yield 54.75%) in the form of yellow powder.

[0089] Among them, the conditions for silica gel column chromatography are: dichloromethane and petroleum ether are selected as solvents, 600g of silica gel (200-300 mesh) is weighed as the adsorbent, petroleum ether is added and stirred until uniform, and then poured into the column, after the silica gel is settled, the mixture is added, the developing agent ratio is dichloromethane: petroleum ether = 1:7, and the eluent is used for purification.

[0090] The reaction route of the above preparation process is as follows:

[0091]

[0092] The obtained organic condensed ring compound C-1-074 was tested and analyzed, and the results are as follows:

[0093] HPLC purity: >99%.

[0094] Mass spectrometry test: theoretical value is 534.66; tested value is 534.21.

[0095] Elemental Analysis:

[0096] The calculated values ​​are: C: 89.86%; H: 4.90%; N: 5.24%;

[0097] The test values ​​are: C: 89.86%; H: 4.91%; N: 5.23%;

[0098] It can be seen from the above test results that Example 2 prepared a high-purity compound of the C-1-074 structure.

[0099] Example 3: Preparation of organic condensed ring compound C-1-101

[0100] Under nitrogen protection system, compound A (24.7mmol), B-1-101 (29.64mmol) (CAS No.: 201802-67-7), potassium carbonate (37.05mmol) were weighed and put into the reaction system, 200mL toluene, 100mL ethanol and 100mL pure water were added, tetrakis(triphenylphosphine)palladium (0.029mmol) was added under nitrogen protection, and the mixture was heated to reflux at 100°C for 36 hours under nitrogen protection. After that, it was cooled to 25°C, and a precipitate was precipitated. The precipitate was filtered, rinsed with water, anhydrous ethanol, and petroleum ether in turn, and then dried. Then, dichloromethane was used as solvent, and silica gel column chromatography was performed. The filtrate was concentrated to solid precipitation to obtain an organic condensed ring compound C-1-080 (8.22g, yield 54.23%) in the form of a yellow powder.

[0101] Among them, the conditions for silica gel column chromatography are: dichloromethane and petroleum ether are selected as solvents, 600g of silica gel (200-300 mesh) is weighed as the adsorbent, petroleum ether is added and stirred until uniform, and then poured into the column, after the silica gel is settled, the mixture is added, the developing agent ratio is dichloromethane: petroleum ether = 1:7, and the eluent is used for purification.

[0102] The reaction route of the above preparation process is as follows:

[0103]

[0104] The obtained organic condensed ring compound C-1-101 was tested and analyzed, and the results were as follows:

[0105] HPLC purity: >99%.

[0106] Mass spectrometry test: theoretical value is 613.76; tested value is 613.25.

[0107] Elemental Analysis:

[0108] The calculated values ​​are: C: 88.06%; H: 5.09%; N: 4.85%;

[0109] The test values ​​are: C: 88.07%; H: 5.10%; N: 4.83%;

[0110] It can be seen from the above test results that Example 3 prepared a high-purity compound of the C-1-101 structure.

[0111] Example 4: Preparation of organic condensed ring compound C-1-128

[0112] Under nitrogen protection system, compound A (24.7mmol), B-1-128 (29.64mmol) (CAS No.: 1246021-71-5), potassium carbonate (37.05mmol) were weighed and put into the reaction system, and a mixed solution of 200mL toluene, 100mL ethanol and 100mL pure water was added. Tetrakis(triphenylphosphine)palladium (0.025mmol) was added under nitrogen protection, and the mixture was heated under reflux at 100°C for 36 hours under nitrogen protection. After that, the mixture was cooled to 25°C, and a precipitate was precipitated. The precipitate was filtered, washed with water, anhydrous ethanol and petroleum ether in turn, and then dried. Then, dichloromethane was used as solvent, and silica gel column chromatography was performed. The filtrate was concentrated to solid precipitation to obtain an organic condensed ring compound C-1-128 (10.11g, yield 56.08%) in the form of yellow powder.

[0113] Among them, the conditions for silica gel column chromatography are: dichloromethane and petroleum ether are selected as solvents, 600g of silica gel (200-300 mesh) is weighed as the adsorbent, petroleum ether is added and stirred until uniform, and then poured into the column, after the silica gel is settled, the mixture is added, the developing agent ratio is dichloromethane: petroleum ether = 1:7, and the eluent is used for purification.

[0114] The reaction route of the above preparation process is as follows:

[0115]

[0116] The obtained compound C-1-128 was tested and analyzed, and the results were as follows:

[0117] HPLC purity: >99%.

[0118] Mass spectrometry test: theoretical value is 729.93; tested value is 729.31.

[0119] Elemental Analysis:

[0120] The calculated values ​​are: C: 88.86%; H: 5.39%; N: 5.76%;

[0121] The test values ​​are: C: 88.87%; H: 5.39%; N: 5.75%;

[0122] It can be seen from the above test results that Example 4 prepared a high-purity compound of C-1-128 structure.

[0123] Example 5: Preparation of organic condensed ring compound C-1-131

[0124] Under nitrogen protection system, compound A (24.7mmol), B-1-131 (29.64mmol) (CAS No.: 2020399-09-9), potassium carbonate (37.05mmol) were weighed and put into the reaction system, 200mL toluene, 100mL ethanol and 100mL pure water were added, tetrakis(triphenylphosphine)palladium (0.025mmol) was added under nitrogen protection, and the mixture was heated to reflux at 100°C for 36 hours under nitrogen protection. After that, it was cooled to 25°C, and a precipitate was precipitated. The precipitate was filtered, rinsed with water, anhydrous ethanol, and petroleum ether in turn, and then dried. Then, dichloromethane was used as solvent, and silica gel column chromatography was performed. The filtrate was concentrated to solid precipitation to obtain an organic condensed ring compound C-1-131 (10.28g, yield 48.74%) in the form of a yellow powder.

[0125] Among them, the conditions for silica gel column chromatography are: dichloromethane and petroleum ether are selected as solvents, 600g of silica gel (200-300 mesh) is weighed as the adsorbent, petroleum ether is added and stirred until uniform, and then poured into the column, after the silica gel is settled, the mixture is added, the developing agent ratio is dichloromethane: petroleum ether = 1:7, and the eluent is used for purification.

[0126] The reaction route of the above preparation process is as follows:

[0127]

[0128] The obtained organic condensed ring compound C-1-131 was tested and analyzed, and the results are as follows:

[0129] HPLC purity: >99%.

[0130] Mass spectrometry test: theoretical value is 853.07; tested value is 854.35.

[0131] Elemental Analysis:

[0132] The calculated values ​​are: C: 90.00%; H: 5.07%; N: 4.92%;

[0133] The test values ​​are: C: 90.00%; H: 5.08%; N: 4.91%;

[0134] It can be seen from the above test results that Example 5 prepared a high-purity compound of C-1-131 structure.

[0135] Example 6: Preparation of organic condensed ring compound C-2-095

[0136] Under nitrogen protection system, compound A (24.7mmol), B-2-095 (29.64mmol) (CAS No.: 2447559-25-1), potassium carbonate (37.05mmol) were weighed and put into the reaction system, and a mixed solution of 200mL toluene, 100mL ethanol and 100mL pure water was added. Tetrakis(triphenylphosphine)palladium (0.025mmol) was added under nitrogen protection, and the mixture was heated to reflux at 100°C for 36 hours under nitrogen protection. After that, the mixture was cooled to 25°C, and a precipitate was precipitated. The precipitate was filtered, washed with water, anhydrous ethanol and petroleum ether in turn, and then dried. Then, dichloromethane was used as solvent, and silica gel column chromatography was performed. The filtrate was concentrated to solid precipitation to obtain an organic condensed ring compound C-2-095 (10.23g, yield 54.87%) in the form of yellow powder.

[0137] Among them, the conditions for silica gel column chromatography are: dichloromethane and petroleum ether are selected as solvents, 600g of silica gel (200-300 mesh) is weighed as the adsorbent, petroleum ether is added and stirred until uniform, and then poured into the column, after the silica gel is settled, the mixture is added, the developing agent ratio is dichloromethane: petroleum ether = 1:7, and the eluent is used for purification.

[0138] The reaction route of the above preparation process is as follows:

[0139]

[0140] The obtained organic condensed ring compound C-2-095 was tested and analyzed, and the results are as follows:

[0141] HPLC purity: >99%.

[0142] Mass spectrometry test: theoretical value is 754.90; tested value is 754.28.

[0143] Elemental Analysis:

[0144] The calculated values ​​are: C: 84.33%; H: 4.54%; N: 11.13%;

[0145] The test values ​​are: C: 84.34%; H: 4.55%; N: 11.11%;

[0146] It can be seen from the above test results that Example 6 prepared a high-purity compound of the C-2-095 structure.

[0147] Example 7-30

[0148] According to the preparation method of the above embodiment, compound A and compound B are replaced by compounds corresponding to the corresponding ligand structures in the target product, and the material dosage is adjusted accordingly according to the corresponding stoichiometric ratio, thereby obtaining the following series of organic condensed ring compounds, see Table 1 below. The products are detected and analyzed according to the detection method in Example 1, and the results show that they are compounds of corresponding structures.

[0149] Table 1 Products of Examples 7 to 30

[0150]

[0151]

[0152] Device Example 1 Preparation of an organic electroluminescent device (OLED) using the above organic condensed ring compound

[0153] The structure of the prepared OLED device is: ITO anode / HIL / HTL / EML / HBL / ETL / EIL / cathode

[0154] a. ITO anode: the coating thickness is The ITO (indium tin oxide) glass substrate was cleaned twice in distilled water and ultrasonically cleaned for 30 minutes, then repeatedly cleaned twice with distilled water and ultrasonically cleaned for 10 minutes. After washing, it was ultrasonically cleaned with methanol, acetone, and isopropanol in sequence (5 minutes each time), dried, and then transferred to a plasma cleaning machine for washing for 5 minutes. It was then sent to a vapor deposition machine, and the substrate was used as the anode, and other functional layers were deposited thereon in sequence.

[0155] b. HIL (hole injection layer): evaporate 2-TNATA (i.e. N1-(2-naphthyl)-N4,N4-di(4-(2-naphthyl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine) to form a hole injection layer.

[0156] c. HTL (hole transport layer): 60 nm of NPB (i.e., N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine) was evaporated to form a hole transport layer.

[0157] d. EML (luminescent layer):

[0158] The light-emitting layer includes an organic light-emitting main material and a doping material. It should be noted that the organic light-emitting main material may include a plurality of main materials. The plurality of main materials include a first main material and a second main material. The first main material may be composed of a single organic condensed ring compound or a plurality of the above-mentioned organic condensed ring compounds, and may further include conventional organic electroluminescent materials in the art. The second main material may be composed of a single second main material or at least one of the above-mentioned second main materials, and may further include conventional organic electroluminescent materials in the art. The current embodiment selects the organic condensed ring compound C-1-013 as the first main material and C-3 as the second main material, and the weight ratio of the first main material to the second main material is 50:50.

[0159] In addition, the doping material contained in the organic electroluminescent device can be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material used in the organic electroluminescent device of the present invention is not particularly limited, but can be selected from metallized composite compounds of iridium (Ir), (Os), copper (Cu) and platinum (Pt). Preferably, it is preferably selected from ortho-metallized complexes of iridium (Ir), (Os), copper (Cu) and platinum (Pt), more preferably ortho-metallized iridium complexes. This embodiment uses the phosphorescent compound shown in European Patent Application 07102949.0 as the doping material in the light-emitting layer. The doping concentration of the doping material in the light-emitting layer is less than about 20% by weight relative to the organic light-emitting main material. This time, a mixed vapor deposition of 30nm with a weight ratio of 90:10 (organic light-emitting main material: doping material) is selected to form a light-emitting layer. The structure of the doping material used in this embodiment is as follows:

[0160]

[0161] e. HBL (hole blocking layer): 10 nm of BAlq was evaporated to form a hole blocking layer.

[0162] f. ETL (electron transport layer): 340nm of Alq was evaporated to form an electron transport layer.

[0163] g. EIL (electron injection layer): LiF 0.2 nm was evaporated to form an electron injection layer.

[0164] h. Cathode: Evaporate 150nm of Al to form a cathode to obtain an OLED device.

[0165] Device Examples 2-30

[0166] Referring to the above method, the organic condensed ring compound C-1-013 is replaced by organic condensed ring compounds C-1-009, C-1-019, C-1-036, C-1-038, C-1-045, C-1-049, C-1-060, C-1-069, C-1-074, C-1-076, C-1-180, C-1-082, C-1-102, C-1-128, C-1-131, C-1-134, C-1-135, C-1- 141, C-1-144, C-1-152, C-1-157, C-1-164, C-1-166, C-2-095, C-2-009, C-2-046, C-2-069, C-2-074, C-2-081, and the second main body C-3 is replaced by the luminescent compounds shown in C-30, C-51, C-85, C-105, C-130 as the main material and the doping material for mixed vapor deposition, and the corresponding organic electroluminescent device is prepared.

[0167] Device Comparative Example 1

[0168] The device comparative example manufactures an organic electroluminescent device. Specifically, according to the preparation method of device embodiment 1, the organic light-emitting main material used in device embodiment 1 is replaced with RH-1 as the main material and mixed with the doping material for evaporation, and the corresponding organic electroluminescent device is prepared. Among them, the structural formula of RH-1 is:

[0169]

[0170] Device Comparison Examples 2-7

[0171] Referring to the above method, according to the preparation method of device embodiment 1, the organic light-emitting host material used in device embodiment 1 is replaced with two existing structures of D-1-1 or D-1-2 as the first host material, and D-2-1, C-3, C-30, C-51, and C-85 are mixed and evaporated with the doping material as the second host material to prepare the corresponding organic electroluminescent device. Among them, the structures of D-1-1, D-1-2, and D-2-1 are as follows:

[0172]

[0173] Performance Test:

[0174] The luminous performance of the organic electroluminescent devices obtained from the above device embodiments 1 to 30 and device comparative examples 1 to 7 was tested under the condition of a brightness of 5000 cd / m2. The driving voltage, luminous life and luminous efficiency were tested using a KEITHLEY 2400 measurement unit and a CS-2000 spectroradiometer. The test results are shown in Table 2:

[0175] Table 2

[0176]

[0177]

[0178] It can be seen from Table 2 that, compared with the existing host materials, the organic condensed ring compound provided by the embodiment of the present invention is used as the main material of the light-emitting layer of the organic electroluminescent device, which can significantly reduce the driving voltage of the organic electroluminescent device and improve the luminous efficiency and service life of the organic electroluminescent device.

[0179] Based on the above ideal embodiments of the present invention, the relevant staff can make various changes and modifications without departing from the technical concept of the present invention through the above description. The technical scope of the present invention is not limited to the contents of the specification, and its technical scope must be determined according to the scope of the claims.

Claims

1. An organic light-emitting host material, characterized in that: The organic light-emitting host material includes a first host material and a second host material; the first host material is an organic condensed ring compound; the structural formula of the second host material is any one of the following structural formulas: The first host material is an organic condensed ring compound, and its structural formula is any one of the following structural formulas:

2. The organic light-emitting host material according to claim 1, characterized in that: The weight ratio of the first main material to the second main material is 1:99-99:

1.

3. An organic electroluminescent device, comprising an anode, a cathode and at least one intermediate layer disposed between the anode and the cathode, wherein the intermediate layer comprises a light-emitting layer, characterized in that: The light-emitting layer partially or entirely comprises the organic light-emitting host material according to any one of claims 1 to 2.

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