Compound and organic electroluminescence device, display device

Abstract

The application relates to the field of electroluminescence, and discloses a compound, an organic electroluminescent device and a display device. The structural formula of the compound is shown in formula (I). The organic electroluminescent device using the compound has a lower driving voltage and a higher current efficiency, and meanwhile, the compound can be used to prepare a transmission layer or an injection layer of the organic electroluminescent device by a solution method.

Description

[0001] This application is a divisional application of patent application No. 202110458920.8 (the original application date is April 27, 2021, and the invention name is Compound and Organic Electroluminescent Device, Display Device). TECHNICAL FIELD

[0002] The present application relates to the field of electroluminescence, in particular to a kind of compound and organic electroluminescent device, display device. BACKGROUND

[0003] At present, organic electroluminescence (OLED) display technology has been applied in the field of smart phones, tablet computers and other fields, and further will be extended to large-size application fields such as television. In the development process of nearly 30 years, people have developed various excellent OLED materials, and through different design of device structure and optimization of device performance such as life and efficiency, the commercialization process of OLED is accelerated, and OLED has been widely used in display and lighting fields.

[0004] However, due to the huge gap between the external quantum efficiency and the internal quantum efficiency of OLED, the development of OLED is greatly restricted, one of the most important factors is that the efficiency of the device has not reached the ideal level. This is because the mode loss of the substrate, the loss of surface plasmon and the waveguide effect, so that most of the light is limited inside the light-emitting device, thereby reducing the light-emitting efficiency of the device. Improving the light-emitting efficiency of the device, using light extraction material is one of the effective methods. Light extraction layer (Capping Layer, CPL) can effectively improve the light extraction efficiency of the device by reducing the surface plasmon effect of the metal electrode, adjusting the light direction and light extraction efficiency, thereby improving the light-emitting efficiency of the device. At present, the types of light extraction materials are relatively single, and the effect is not ideal, and it is one of the more severe challenges faced by OLED workers to develop more effective light extraction materials.

[0005] In addition, the selection of light-emitting layer and other organic functional layer materials also has a great influence on the current efficiency and driving voltage of the device, and the functional layer materials with higher performance are still being explored.

[0006] Therefore, in order to meet the higher requirements of people for OLED devices, more types and higher performance of OLED materials need to be developed in this field. SUMMARY

[0007] In view of the deficiencies of the prior art, the purpose of the present application is to provide a compound and an organic electroluminescent device and a display device. The organic electroluminescent device using the material of the present application has a lower driving voltage and a higher current efficiency, and the compound provided by the present application can be used to prepare a transport layer or an injection layer of an organic electroluminescent device by a solution method.

[0008] To achieve the above purpose, the present application adopts the following technical solutions:

[0009] In a first aspect, the present application provides a compound, the structure of the compound is shown in formula (I),

[0010]

[0011] wherein a, b, c, d are each independently selected from 0, 1, 2, 3 or 4; p is selected from 0 or 1;

[0012] R1-R4 are each independently selected from hydrogen, deuterium, F, CN, an alkyl group containing 1-20 carbon atoms, an alkoxy group containing 1-20 carbon atoms, an aromatic group containing 6-40 carbon atoms; the hydrogen in the aromatic group containing 6-40 carbon atoms can be substituted by R; wherein R can form a ring with the spirofluorene, and Ar can form a ring with Ar1 and Ar2;

[0013] Ar, Ar1 are each independently selected from an aromatic group containing 6-40 carbon atoms, and the hydrogen in the aromatic group containing 6-40 carbon atoms can be substituted by R;

[0014] Ar2 is selected from one of the structures shown in A-1 to A-8:

[0015]

[0016]

[0017] wherein * indicates the position of the connection between Ar2 and the N atom in formula (I);

[0018] R5-R 14 are each independently selected from an alkyl group containing 1-20 carbon atoms, an aromatic group containing 6-40 carbon atoms; the hydrogen in the aromatic group containing 6-40 carbon atoms can be substituted by R;

[0019] e, f are each independently selected from 0 or 1, and e, f are not simultaneously 0;

[0020] R is selected from an alkyl group containing 1-20 carbon atoms, an alkoxy group containing 1-20 carbon atoms, or an aromatic group containing 6-40 carbon atoms.

[0021] The following are preferred technical solutions of the present application, but not as a limitation of the technical solutions provided by the present application, through the following preferred technical solutions, the purpose and beneficial effects of the present application can be better achieved and realized.

[0022] As a preferred technical solution of the present application, Ar1 is selected from one of B-1 to B-4:

[0023]

[0024] R 21 ~R 22 Each is independently selected from an alkyl group containing 1 to 20 carbon atoms, an aromatic group containing 6 to 40 carbon atoms; the hydrogen in the aromatic group containing 6 to 40 carbon atoms can be substituted by R; R 21 ~R 22 Can be connected into a ring; Ar3, Ar4 are each independently selected from an aromatic group containing 6 to 40 carbon atoms, the hydrogen in the aromatic group containing 6 to 40 carbon atoms can be substituted by R; p, q are selected from 0 or 1;

[0025] Wherein * indicates the position of the N atom connected in B-1 to B-4 and formula (I).

[0026] Further, when R1 to R4 are selected from an aromatic group containing 6 to 40 carbon atoms substituted by an alkyl group containing 1 to 20 carbon atoms, the alkyl group containing 1 to 20 carbon atoms can be annulated with the spirofluorene group.

[0027] The present application also provides a synthesis method of the compound shown in formula (I):

[0028]

[0029] The present application also provides another synthesis method of the compound shown in formula (I):

[0030]

[0031] Wherein X is selected from Cl, Br, I.

[0032] The present application also provides the following intermediates for synthesizing the compound shown in formula (I):

[0033]

[0034] Wherein X is selected from Cl, Br, I.

[0035] As a preferred technical solution of the present application, the structure of the compound is selected from one of the following structures:

[0036]

[0037]

[0038] As a preferred technical scheme of the present application, in the compound II-1 to compound II-9, Ar1, Ar is selected from benzene, biphenyl, naphthalene, phenanthrene, fluorene, carbazole, dibenzofuran, dibenzothiophene, triphenylene, fluoranthene or one of Ar2, and the hydrogen in Ar1, Ar can be substituted by alkyl of 1-20 carbon atoms, aromatic group containing 6-40 carbon atoms.

[0039] When the hydrogen in Ar, Ar1 is substituted by aromatic group containing 6-40 carbon atoms, Ar, Ar1 can be annelated by carbon atom with aromatic group containing 6-40 carbon atoms, can be annelated by N-R, can be annelated by O, S, R is selected from alkyl of 1-20 carbon atoms, aromatic group containing 6-40 carbon atoms; Ar can be annelated by substituent and spirofluorene.

[0040] As a preferred technical scheme of the present application, in the compound II-1 to compound II-9:

[0041] p is selected from 1;

[0042] Ar1 is selected from benzene, biphenyl, naphthalene, phenanthrene, fluorene, carbazole, dibenzofuran, dibenzothiophene, triphenylene, fluoranthene, and the hydrogen in Ar1 can be substituted by alkyl of 1-6 carbon atoms, aromatic group containing 6-12 carbon atoms;

[0043] Ar is selected from benzene, biphenyl, spirofluorene, naphthalene, phenanthrene, fluorene, carbazole, dibenzofuran, dibenzothiophene, triphenylene, fluoranthene, and the hydrogen in Ar can be substituted by alkyl of 1-6 carbon atoms, aromatic group containing 6-12 carbon atoms.

[0044] As a preferred technical scheme of the present application, in the compound II-1 to compound II-9, p is selected from 0; Ar1 is selected from benzene, biphenyl, naphthalene, phenanthrene, fluorene, carbazole, dibenzofuran, dibenzothiophene, triphenylene, fluoranthene, and the hydrogen in Ar1 can be substituted by alkyl of 1-6 carbon atoms, aromatic group containing 6-12 carbon atoms.

[0045] As a preferred technical scheme of the present application, the compound is selected from any one of the following compounds:

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057] In the present application, P-1 to P-132 structural isomers refer to different connection modes between the aromatic rings constituting Ar, different connection modes between the aromatic rings constituting Ar1, the position of the SP2 hybridized carbon atom on N atom connected with Ar2, and different connection positions of the substituents on Ar2 in the specific structures of P-1 to P-132.

[0058] For example, the following is provided:

[0059] For P-3, when the two benzene rings of the biphenyl group are connected in any mode and / or any one of the SP2 hybridized carbon atoms of the tetramethyldihydrophenanthrene group is connected to the N atom, all of them are considered to be structural isomers of P-3, including but not limited to the following structures:

[0060]

[0061] For P-1 to P-132 structural isomers, the above explanation of P-3 can be referred to for understanding.

[0062] In a second aspect, the present application provides a compound intermediate, which is selected from one of the following structures:

[0063]

[0064] In a third aspect, the present application provides an organic electroluminescent device, which comprises the compound according to the first aspect.

[0065] In a fourth aspect, the present application provides a display device, which comprises the organic electroluminescent device according to the third aspect.

[0066] Compared with the prior art, the present application has the following beneficial effects:

[0067] The application provides a compound shown in formula (I), taking a spirofluorene group as a mother nucleus and limiting the selection range of each substituent group, so that the film forming property and light transmittance of the material are improved, and the material is greatly improved compared with prior art materials. Meanwhile, the structure of the compound is changed, and the solubility of the material in an organic solvent is changed accordingly. After the compound solution is dissolved in the solvent, an organic solvent with good viscosity performance can be obtained. After the solvent is volatilized, the film forming property of the remaining organic material is excellent, so that the material is more suitable for being prepared by using a solution method when being used for preparing an OLED device. Meanwhile, the change of the structure of the compound improves the HOMO and LOMO energy levels of the material, so that the material as a host material, a hole injection layer (HIL) material or a hole transport layer (HTL) material has high light emitting efficiency and low driving voltage when being applied to an OLED device. BRIEF DESCRIPTION OF DRAWINGS

[0068] Figure 1 A mass spectrum detection diagram of a compound P-5 provided by the embodiment of the application is provided.

[0069] Figure 2 A mass spectrum detection diagram of a compound P-6 provided by the embodiment of the application is provided. DETAILED DESCRIPTION

[0070] The technical solutions of the application will be further described below by means of specific embodiments and in conjunction with the drawings. Those skilled in the art should understand that the embodiments are only used to help understand the application, and should not be regarded as specific limitations on the application.

[0071] The technical solutions in the embodiments of the application will be clearly and completely described below in conjunction with the embodiments of the application. Obviously, the described embodiments are only part of the embodiments of the application, rather than all the embodiments of the application. Based on the embodiments in the application, all other embodiments obtained by those skilled in the art without creative work fall within the scope of protection of the application.

[0072] It should be noted that: in the application, all the embodiments and preferred implementation methods mentioned in the present text can be combined to form new technical solutions, unless otherwise specified. In the application, unless otherwise specified, the numerical range "a~b" represents a shorthand representation of any real number combination between a and b, where a and b are real numbers. For example, the numerical range "6~22" represents that all real numbers between "6~22" have been listed in the present text, and "6~22" is only a shorthand representation of these numerical combinations. The lower limit and the upper limit of the range disclosed in the application can be one or more lower limits and one or more upper limits, respectively. In the application, unless otherwise specified, each reaction or operation step can be performed in sequence or not in sequence. Preferably, the reaction method in the present text is performed in sequence.

[0073] Unless otherwise indicated, the professional and scientific terms used herein have the same meaning as those familiar to those skilled in the art. In addition, any method or material similar or equivalent to those described can also be applied to the present application.

[0074] Synthesis of Example 1

[0075] Synthesis of P-1

[0076] Synthesis of 4-bromo-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene and 2-bromo-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene

[0077]

[0078] Into a 250ml three-necked flask, 0.01mol (2.36g) of 9,9,10,10-tetramethyl-9,10-dihydrophenanthrene, 30ml of dichloromethane, 5ml of glacial acetic acid, 0.2g of iron powder were added, then 0.012mol (1.92g) of liquid bromine was slowly added dropwise in 5ml of dichloromethane, and the temperature was controlled at 20-25°C, and the reaction was carried out for 4 hours after the addition was completed. Water was added for stirring, the insoluble matter was filtered, the mother liquor was separated, the organic layer was washed with sodium bisulfite solution, then washed with water until neutral, concentrated to dryness, and separated by silica gel column chromatography with petroleum ether elution to obtain 0.81g of 4-bromo-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene and 0.92g of 2-bromo-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene, with a total yield of 54.9%.

[0079] The obtained 4-bromo-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene was subjected to mass spectrometry detection, and the molecular m / z was determined to be: 314, 316, and the molecular formula of the product was determined to be C 18 H 19 Br.

[0080] The obtained 4-bromo-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene was subjected to nuclear magnetic detection, and the data analysis was as follows: 1H-NMR (Switzerland Bruker Company, Avance II 400MHz nuclear magnetic resonance spectrometer, CDCl3), δ 7.71 (m, 1H), δ 7.66 (m, 1H), δ 7.55 (m, 1H), δ 7.48 (m, 1H), δ 7.34-7.28 (m, 2H), δ 7.21 (t, 1H), δ 1.33 (s, 12H).

[0081] The obtained 2-bromo-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene was subjected to mass spectrometry detection, and the molecular m / z was determined to be: 314, 316, and the molecular formula of the product was determined to be C 18H 19 Br.

[0082] The 2-bromo-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene obtained was subjected to nuclear magnetic detection, and the data were analyzed as follows:1H-NMR (Switzerland Bruker Company, Avance II 400 MHz nuclear magnetic resonance spectrometer, CDCl3), δ 7.71 (m, 1H), δ 7.67 (d, 1H), δ 7.61-7.53 (m, 2H), δ 7.46 (m, 1H), δ 7.35-7.26 (m, 2H), δ 1.33 (s, 12H).

[0083] Step S2) Synthesis of 2-(9,9,10,10-tetramethyl-9,10-dihydrophenanthrene-4-yl)-2-propanol

[0084]

[0085] A 250 mL three-necked flask was charged with 0.01 mol (3.15 g) of 4-bromo-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene, 100 mL of tetrahydrofuran, and after nitrogen replacement, the temperature was lowered to -78°C, then 0.012 mol of butyllithium in n-hexane solution (7.5 mL, concentration 1.6 M) was added dropwise, after the addition was completed, the temperature was kept at -70 to -78°C for 30 min, then 0.02 mol (1.16 g) of acetone was added at one time, then the temperature was slowly raised to 25°C, ammonium chloride solution was added for hydrolysis, then dichloromethane was added for liquid separation, after the organic layer was washed to neutral, it was concentrated and dried under reduced pressure to obtain a yellow oil, which was not separated and directly subjected to the next reaction.

[0086] Step S3) Synthesis of 4,4,8,8,9,9-hexamethyl-8,9-dihydro-4H-cyclopenta[def]phenanthrene

[0087]

[0088] Under nitrogen protection, 20 mL of dichloromethane was added to the unseparated 2-(9,9,10,10-tetramethyl-9,10-dihydrophenanthrene-4-yl)-2-propanol obtained in the previous step, which was stirred and dissolved, then 3 mL of glacial acetic acid was added, the temperature was lowered to 0°C, and 2 g of methyl sulfonic acid was slowly added dropwise while keeping the temperature at 0-5°C, after the addition was completed, the temperature was raised to 25°C, then the reaction was carried out for 4 hours, then 30 mL of methanol was added, a solid was precipitated, which was filtered, the solid was washed with methanol, and dried to obtain a white solid 4,4,8,8,9,9-hexamethyl-8,9-dihydro-4H-cyclopenta[def]phenanthrene, 1.88 g, total yield 68% from the previous step.

[0089] The mass spectrum of 4,4,8,8,9,9-hexamethyl-8,9-dihydro-4H-cyclopenta[def]phenanthrene was detected, and the molecular m / z was determined to be 276.

[0090] Step S4) Synthesis of 2-bromo-4,4,8,8,9,9-hexamethyl-8,9-dihydro-4H-cyclopenta[def]phenanthrene

[0091]

[0092] A 250 mL three-necked flask was charged with 0.01 mol (2.76 g) of 4,4,8,8,9,9-hexamethyl-8,9-dihydro-4H-cyclopenta[def]phenanthrene, 40 mL of dichloromethane, 15 mL of glacial acetic acid, and 0.2 g of iron powder, and then a solution of 0.012 mol (1.92 g) of liquid bromine in 5 mL of dichloromethane was slowly added dropwise while controlling the temperature at 20-25°C. After the addition was completed, the reaction was allowed to proceed at 35-40°C for 4 hours. Water was added and stirred, the insoluble matter was filtered, and the mother liquor was separated. The organic layer was washed with sodium bisulfite solution and then with water until neutral. After being concentrated to dryness, the product 2-bromo-4,4,8,8,9,9-hexamethyl-8,9-dihydro-4H-cyclopenta[def]phenanthrene was separated by silica gel column chromatography using petroleum ether as the eluent, and 2.18 g of the product was obtained.

[0093] The mass spectrum of 2-bromo-4,4,8,8,9,9-hexamethyl-8,9-dihydro-4H-cyclopenta[def]phenanthrene was detected, and the molecular m / z was determined to be 354, 356, and the molecular formula of the product was determined to be C 21 H 23 Br.

[0094] Step S5) Synthesis of P-1

[0095]

[0096] A 250 mL three-necked flask was charged with 150 mL of dry toluene, 4.84 g (0.01 mol) of N-([1,1'-biphenyl]-3-yl)-9,9'-spirobifluorene-2-amine, 3.91 g (0.011 mol) of 2-bromo-4,4,8,8,9,9-hexamethyl-8,9-dihydro-4H-cyclopenta[def]phenanthrene, 0.0575 g (0.0001 mol) of Pd(dba)2 (bisbenzylideneacetone palladium), 0.4 g (0.0002 mol) of a toluene solution containing 10% tri-tert-butylphosphine, and 1.44 g (0.015 mol) of sodium tert-butoxide, and the reaction was allowed to proceed at reflux for 6 hours under nitrogen protection. After cooling, water was added and the mixture was separated. The organic layer was washed with water until neutral, dried over magnesium sulfate, filtered, concentrated to dryness, and recrystallized from a mixture of chloroform and methanol to obtain 6.12 g of the compound represented by P-1, with a yield of 80.74%.

[0097] The compound shown as P-1 was subjected to mass spectrometry, and the molecular m / z was determined to be: 757.

[0098] The compound shown as P-1 was subjected to nuclear magnetic detection, and the data were analyzed as follows: 1H-NMR (Switzerland Bruker Company, Avance II 400 MHz nuclear magnetic resonance spectrometer, CDCl3), δ 7.93-7.84 (m, 4H), δ 7.77 (m, 2H), δ 7.65 (m, 2H), δ 7.59-7.46 (m, 5H), δ 7.45-7.31 (m, 7H), δ 7.28-7.21 (m, 6H), δ 7.20-7.13 (m, 3H), δ 1.70 (s, 6H), δ 1.34 (s, 12H).

[0099] Synthesis Example 2

[0100] Synthesis of P-5

[0101]

[0102] The synthesis method refers to the synthesis of P-1, and the difference from the synthesis method of compound P-1 is that N-([1,1'-biphenyl]-3-yl)-9,9'-spirobifluorene-2-amine in it is replaced by N-([1,1'-biphenyl]-4-yl)-9,9'-spirobifluorene-2-amine, and 2-bromo-4,4,8,8,9,9-hexamethyl-8,9-dihydro-4H-cyclopenta[def]phenanthrene is replaced by 9-bromo-7,7-dimethyl-7H-benzo[c]fluorene, to obtain the compound shown as P-5.

[0103] The compound shown as P-5 was subjected to mass spectrometry, and the molecular m / z was determined to be: 725. Figure 1

[0104] Synthesis Example 3

[0105] Synthesis of P-6

[0106]

[0107] The synthesis method refers to the synthesis of P-1, and the difference from the synthesis method of compound P-1 is that N-([1,1'-biphenyl]-3-yl)-9,9'-spirobifluorene-2-amine in it is replaced by N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobifluorene-2-amine, and 2-bromo-4,4,8,8,9,9-hexamethyl-8,9-dihydro-4H-cyclopenta[def]phenanthrene is replaced by 9-bromo-7,7-dimethyl-7H-benzo[c]fluorene, to obtain the compound shown as P-6.

[0108] ​The compound shown as P-17 was subjected to mass spectrometry detection, and the spectrum is shown in Figure Figure 2 The molecular m / z was determined to be 765.

[0109] Synthesis Example 4

[0110] Synthesis of P-17

[0111]

[0112] The synthesis method was referred to the synthesis of P-1, and the difference from the synthesis method of the compound P-1 was that N-([1,1'-biphenyl]-3-yl)-9,9'-spirobifluorene-2-amine in it was replaced by N-(4-fluorophenyl)-9,9'-spirobifluorene-2-amine, and 2-bromo-4,4,8,8,9,9-hexamethyl-8,9-dihydro-4H-cyclopenta[def]phenanthrene in it was replaced by 3-bromo-7,7-dimethyl-7H-benzo[de]anthracene, to obtain the compound shown as P-17.

[0113] The compound shown as P-17 was subjected to mass spectrometry detection, and the molecular m / z was determined to be 667.

[0114] Synthesis Example 5

[0115] Synthesis of P-44

[0116]

[0117] 1) First, 9,9'-spirobifluorene-2-amine and 5-bromo-7,7-dimethyl-7H-benzo[c]fluorene were reacted to obtain the compound shown as P-44-1.

[0118] The compound shown as P-44-1 was subjected to mass spectrometry detection, and the molecular m / z was determined to be 573.

[0119]

[0120] 2) The compound shown as P-44-1 was reacted with the compound shown as P-44-2 to obtain the compound shown as P-44.

[0121] The compound shown as P-44 was subjected to mass spectrometry detection, and the molecular m / z was determined to be 890.

[0122] Synthesis Example 6

[0123] Synthesis of P-79

[0124]

[0125] The compound shown as P-79-1 was reacted with the compound shown as 3-bromo-7,7-dimethyl-7H-benzo[de]anthracene to obtain the compound shown as P-79.

[0126] The compound shown as P-79 was subjected to mass spectrometry to determine the molecular m / z as: 801.

[0127] Synthesis Example 7

[0128] Synthesis of P-102

[0129] 1) Synthesis of P-102-1

[0130]

[0131] Into a 250 mL three-necked flask, 100 mL of DMF, 2.48 g of 3-bromo- diphenylamine, 2.33 g of 3-chloro-4-nitro-l, l'-biphenyl, 1.3 g of sodium carbonate were added, and the mixture was slowly warmed to 60°C and reacted for 2 hours, then warmed to 100°C and reacted for 1 hour. After cooling, water was added, and the obtained solid was filtered and recrystallized from ethanol to obtain P-102-1, 3.8 g in weight.

[0132] The compound shown as P-102-1 was subjected to mass spectrometry, and the two largest peaks had substantially the same peak height, m / z: 446, 444, and the product molecular formula was determined as: C 24 H 17 BrN2O2.

[0133] 2) Synthesis of P-102-2

[0134]

[0135] Into a 500 mL flask, 4.45 g of the compound shown as P-102-1, 100 mL of o-dichlorobenzene, and 16 g of triethyl phosphite were added under nitrogen protection, and the mixture was heated to reflux and reacted for 8 hours. After cooling, 100 mL of 10% sodium hydroxide solution was added, and the mixture was stirred at room temperature for 8 hours. After separation, the organic layer was washed with water, dried over magnesium sulfate, filtered, and the filtrate was concentrated to obtain P-102-2, which was recrystallized from a mixture of toluene and ethanol to obtain P-102-2, 1.8 g in weight.

[0136] The compound shown as P-102-2 was subjected to mass spectrometry, and the two largest peaks had substantially the same peak height, m / z: 414, 412, and the product molecular formula was determined as: C 24 H 17 BrN2.

[0137] 3) Synthesis of 3-iodo-7,7-dimethyl-7H-benzo[de]anthracene

[0138]

[0139] 500 mL three-necked flask, 4.13 g of P-102-2, 3.70 g of 3-iodo-7,7-dimethyl-7H- benzo[de]anthracene, 0.2 g of cuprous iodide, 0.2 g of o-phenanthroline (cas no. 66-71-7), 100 mL of chlorobenzene, 1.2 g of sodium carbonate were added, heated to reflux for 24 hours, cooled, stirred with water, filtered to remove insoluble matter, separated, the organic layer was washed with water until neutral, concentrated to dryness, separated by silica gel column chromatography, eluted with petroleum ether, to obtain P-102-3, 4.6 g.

[0140] The compound represented by P-102-3 was subjected to mass spectrometry, and the two largest peaks had substantially the same peak height, m / z: 656, 654, and the molecular formula of the product was determined to be: C

[0141] 4) Synthesis of P-102-3

[0142]

[0143] 500 mL three-necked flask, 4.13 g of P-102-2, 3.70 g of 3-iodo-7,7-dimethyl-7H- benzo[de]anthracene, 0.2 g of cuprous iodide, 0.2 g of o-phenanthroline (cas no. 66-71-7), 100 mL of chlorobenzene, 1.2 g of sodium carbonate were added, heated to reflux for 24 hours, cooled, stirred with water, filtered to remove insoluble matter, separated, the organic layer was washed with water until neutral, concentrated to dryness, separated by silica gel column chromatography, eluted with petroleum ether, to obtain P-102-3, 4.6 g.

[0144] The compound represented by P-102-3 was subjected to mass spectrometry, and the two largest peaks had substantially the same peak height, m / z: 656, 654, and the molecular formula of the product was determined to be: C 43 H 31 BrN2.

[0145] 5) Synthesis of P-102

[0146]

[0147] 250 mL three-necked flask, 4.13 g of P-102-2, 3.70 g of 3-iodo-7,7-dimethyl-7H- benzo[de]anthracene, 0.2 g of cuprous iodide, 0.2 g of o-phenanthroline (cas no. 66-71-7), 100 mL of chlorobenzene, 1.2 g of sodium carbonate were added, heated to reflux for 24 hours, cooled, stirred with water, filtered to remove insoluble matter, separated, the organic layer was washed with water until neutral, concentrated to dryness, separated by silica gel column chromatography, eluted with petroleum ether, to obtain P-102-3, 4.6 g.

[0148] The compound represented by P-102-3 was subjected to mass spectrometry, and the two largest peaks had substantially the same peak height, m / z: 656, 654, and the molecular formula of the product was determined to be: C

[0149] The synthesis of the products not listed in the above synthesis examples can be carried out by using methods known in the art and by using conventional means to synthesize.

[0150] Device Example

[0151] The specific structures of several materials used in the present application are as follows:

[0152]

[0153] Device Example 1

[0154] In the comparative examples, HT-1 to HT-3 were used as the hole transport material in the organic electroluminescent device.

[0155] The structure of the organic electroluminescent device was: ITO / HIL02 (100 nm) / hole transport material (40 nm) / EM39 (30 nm) / TPBI (30 nm) / LiF (0.5 nm) / Al (150 nm).

[0156] The preparation process of the organic electroluminescent device was as follows:

[0157] The glass substrate coated with the ITO transparent conductive layer (as an anode) was subjected to ultrasonic treatment in a cleaning agent, then washed in deionized water, then subjected to ultrasonic oil removal in a mixed solvent of acetone and ethanol, then baked in a clean environment until completely water-free, washed with ultraviolet light and ozone, and the surface was bombarded with a low-energy cation beam to improve the surface properties and improve the binding ability with the hole injection layer.

[0158] The above glass substrate was placed in a vacuum chamber, vacuumed to 1 x 10 -5 ~ 9 x 10 -3 Pa, and HIL02 was vacuum evaporated on the anode as a hole injection layer, with an evaporation rate of 0.1 nm / s and a film thickness of 100 nm.

[0159] The compound of the present application and the comparative material were vacuum evaporated on the hole injection layer as a hole transport layer, with an evaporation rate of 0.1 nm / s and a film thickness of 40 nm.

[0160] EM39 was vacuum evaporated on the hole transport layer as an organic light-emitting layer of the device, with an evaporation rate of 0.1 nm / s and a total film thickness of 30 nm.

[0161] TPBI was vacuum evaporated on the organic light-emitting layer as an electron transport layer of the organic electroluminescent device, with an evaporation rate of 0.1 nm / s and a total film thickness of 30 nm.

[0162] 0.5nm of LiF, 150nm of Al were vacuum evaporated on the electron transport layer as electron injection layer and cathode.

[0163] The luminance, driving voltage, and current efficiency of the prepared organic electroluminescent device were measured.

[0164] The performance of the organic electroluminescent device is shown in Table 1 below. The OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang was used for testing

[0165] Table 1

[0166] Hole transport material Requesting brightness cd / m 2 ]]> Driving voltage V Current efficiency cd / A HT-1 1000 6.33 1.76 HT-2 1000 6.29 1.87 HT-3 1000 6.66 1.58 P-1 1000 5.96 1.93 P-2 1000 5.76 2.02 P-5 1000 5.71 2.01 P-6 1000 5.32 2.13 P-60 1000 5.33 2.26 P-103 1000 5.28 2.29 P-110 1000 5.08 2.22 P-123 1000 5.11 2.13 P-127 1000 4.56 2.56 P-131 1000 4.66 2.66 P-132 1000 4.61 2.55

[0167] Device Example 2

[0168] In this example, the compound of the present application was selected as a hole transport material in an organic electroluminescent device, and comparative example HT-1 was selected as a hole transport material in an organic electroluminescent device, and in this example, the hole transport layer was prepared by a solution method.

[0169] The structure of the organic electroluminescent device was: ITO / HIL02(100nm) / hole transport material / EM39(30nm) / TPBI(30nm) / LiF(0.5nm) / Al(150nm).

[0170] The preparation process of the organic electroluminescent device was as follows:

[0171] The glass substrate coated with an ITO transparent conductive layer (as an anode) was subjected to ultrasonic treatment in a cleaning agent, then rinsed in deionized water, then ultrasonic oil removal in a mixed solvent of acetone and ethanol, then baked in a clean environment until completely water-free, washed with ultraviolet light and ozone, and the surface was bombarded with a low-energy cation beam to improve the surface properties and improve the binding ability with the hole injection layer.

[0172] The above glass substrate was placed in a vacuum chamber, vacuumed to 1×10 -5 ~ 9×10 -3 Pa, vacuum evaporated HIL02 on the anode as a hole injection layer, the evaporation rate was 0.1 nm / s, and the evaporation film thickness was 100 nm.

[0173] The glass substrate on which the hole injection layer has been deposited was transferred into a glove box filled with nitrogen, and a chlorobenzene solution of the compound of the present application and the comparative compound was spin-coated on the hole injection layer at a rotation speed of 1000 rpm for 60 seconds. The thickness of the hole transport layer was adjusted to be 45-55 nm by adjusting the concentration of the compound of the present application and the comparative compound in the solvent. Then, the glass substrate was heated at 80°C for 2 hours, and the solvent was removed in vacuum. The thickness of the hole transport layer was measured by a surface profiler (model Amibios XP-2 surface profiler), and is shown in the following table.

[0174] The glass substrate on which the hole transport layer has been spin-coated was transferred into a vacuum chamber, and EM39 was vacuum-deposited on the hole transport layer as the organic light-emitting layer of the device at a deposition rate of 0.1 nm / s, and the total film thickness was 30 nm.

[0175] TPBI was vacuum-deposited on the organic light-emitting layer as the electron transport layer of the organic electroluminescent device at a deposition rate of 0.1 nm / s, and the total film thickness was 30 nm.

[0176] 0.5 nm of LiF and 150 nm of Al were vacuum-deposited on the electron transport layer as the electron injection layer and the cathode.

[0177] The brightness, driving voltage, and current efficiency of the prepared organic electroluminescent device were measured.

[0178] The performance of the organic electroluminescent device is shown in Table 2 below. The OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang was used for testing.

[0179] Table 2

[0180]

[0181]

[0182] Device Example 3

[0183] In the examples, the compound of the present application was selected as the green light host material in the organic electroluminescent device, and in the comparative examples, GH-1 and GH-2 were selected as the green light host material in the organic electroluminescent device.

[0184] The structure of the organic electroluminescent device is: ITO / NPB (20 nm) / green host material (30 nm): Ir(ppy)3 [7%] / TPBI (10 nm) / Alq3 (15 nm) / LiF (0.5 nm) / Al (150 nm). Wherein "Ir(ppy)3 [7%]" refers to the doping ratio of green dye, i.e. the weight ratio of green host material to Ir(ppy)3 is 100:7.

[0185] The preparation process of the organic electroluminescent device is as follows: the glass plate coated with ITO transparent conductive layer is ultrasonically treated in a commercial cleaning agent, washed in deionized water, ultrasonically degreased in a mixed solvent of acetone: ethanol, baked in a clean environment until the water is completely removed, cleaned with ultraviolet light and ozone, and the surface is bombarded with low-energy cation beam;

[0186] The above glass substrate with anode is placed in a vacuum chamber, vacuumed to 1x10 -5 ~ 9x10 -3 Pa, vacuum evaporating hole transport layer NPB on the anode layer film, the evaporation rate is 0.1 nm / s, and the evaporation film thickness is 20 nm;

[0187] Vacuum evaporating green host material and dye Ir(ppy)3 on the hole transport layer as the light-emitting layer of the organic electroluminescent device, the evaporation rate is 0.1 nm / s, and the total evaporation film thickness is 30 nm;

[0188] Vacuum evaporating electron transport layer TPBI and Alq3 on the light-emitting layer in turn, the evaporation rate is 0.1 nm / s, and the evaporation film thickness is 10 nm and 15 nm respectively;

[0189] Vacuum evaporating 0.5 nm of LiF and 150 nm of Al on the electron transport layer as the electron injection layer and cathode.

[0190] All the organic electroluminescent devices are prepared by the above method, the only difference is the selection of green host material, see Table 3 below for details.

[0191] Performance test:

[0192] The luminance, driving voltage and current efficiency of the prepared organic electroluminescent device are measured by using OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang, and the test results are shown in the following table.

[0193] Table 3

[0194]

[0195]

[0196] From the above table, compared with the comparative compounds, the compound provided by the application can improve the luminous efficiency and reduce the driving voltage as the green light host material of the organic electroluminescence device.

[0197] Obviously, persons having ordinary skill in the art can make various modifications and variations to the embodiments of the application without departing from the spirit and scope of the application. Thus, if these modifications and variations of the application belong to the scope of the claims of the application and the equivalent technologies thereof, the application also intends to include these modifications and variations.

Claims

1. A compound, characterized in that, The compound is .

2. A compound intermediate, characterized in that, The compound intermediate is selected from one of the following structures: 。 3. An organic electroluminescent device, characterized by comprising The organic electroluminescence device comprises the compound according to claim 1.

4. A display device, characterized by comprising: The organic electroluminescence device comprises the compound according to claim 3.

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