CN116462593B - Organic light-emitting auxiliary material, preparation method thereof and application thereof in organic electroluminescent device - Google Patents

Organic light-emitting auxiliary material, preparation method thereof and application thereof in organic electroluminescent device Download PDF

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CN116462593B
CN116462593B CN202310695762.7A CN202310695762A CN116462593B CN 116462593 B CN116462593 B CN 116462593B CN 202310695762 A CN202310695762 A CN 202310695762A CN 116462593 B CN116462593 B CN 116462593B
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auxiliary material
emitting auxiliary
organic light
compound
organic
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CN116462593A (en
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汪康
孟范贵
金成寿
张雪
段晓伟
赵贺
孙峰
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The invention belongs to the technical field of organic photoelectric materials, and particularly provides an organic light-emitting auxiliary material, a preparation method thereof and application thereof in an organic electroluminescent device, wherein the structural general formula of the organic light-emitting auxiliary material is shown in the specification. The organic light-emitting auxiliary material provided by the invention can ensure the space torsion of a molecular structure through arylene bridging adamantane and 9-methylfluorenyl, and avoid the phenomena of large intermolecular interaction, poor service life of devices and low light-emitting efficiency caused by molecular stacking; the molecular structure can be prolonged by means of bridging, the mobility of the molecules is improved, and the hole transport is facilitated; meanwhile, the HOMO energy level of the molecule can be regulated by selecting different aryl or heteroaryl in the aromatic amine, so that the material is suitable for different device collocations.

Description

Organic light-emitting auxiliary material, preparation method thereof and application thereof in organic electroluminescent device
Technical Field
The invention relates to the technical field of organic photoelectric materials, in particular to an organic light-emitting auxiliary material, a preparation method thereof and an organic electroluminescent device.
Background
An organic electroluminescent device (OLED) is an optoelectronic device based on electroluminescent characteristics of an organic material, and has important application value in the fields of illumination and new generation flat panel display. Compared with the traditional display and illumination technology, the display device has obvious advantages such as no need of a backlight source, light weight, low energy consumption, high response speed, flexibility, clearness, no smear and the like for displaying moving images, and can meet the performance requirements of people on an information display system in multiple aspects.
The OLED presents multilayer as "sandwich type structural feature, specifically includes electrode material rete and presss from both sides the organic functional material between different electrode retes, includes: a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an emission layer (EML), an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL). In the current research, in order to reduce the potential barrier between the HTL and the EML and reduce the driving voltage of the OLED, a light-emitting auxiliary layer is generally disposed between the HTL and the EML to increase the utilization rate of holes, thereby improving the light-emitting efficiency, stability and lifetime of the OLED.
In recent years, many studies have been conducted on materials for light-emitting auxiliary layers, but materials excellent in device performance have been rarely found, particularly in terms of improving light-emitting efficiency and increasing device lifetime. Therefore, there is still much development room for research on OLED light-emitting auxiliary materials, and finding light-emitting auxiliary materials that are developed in match with current or future OLED technologies is a problem that needs to be solved urgently by those skilled in the art.
Disclosure of Invention
In view of the above, the present invention provides an organic light emitting auxiliary material and a preparation method thereof, and in particular provides a red and green light emitting auxiliary material containing 9-methyl-9-phenylfluorenyl and 1-aryladamantanyl substituted aromatic amine structures.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
the first technical object of the present invention is to provide an organic light-emitting auxiliary material, which has a structure shown in formula I:
；
i is a kind of
Wherein, the liquid crystal display device comprises a liquid crystal display device,
ar is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-membered to 30-membered heteroaryl;
Ar 1 a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted 3-to 30-membered heteroaryl group;
R 1 、R 2 independently selected from hydrogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C30 aryl;
n is 1 or 2.
Further, ar 1 Selected from hydrogen;
Ar、Ar 1 、R 1 、R 2 when selected from the group consisting of substituted or unsubstituted C6-C30 aryl, it is preferably phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, benzofluorenyl, phenanthryl, anthracenyl, indenyl, triphenylenyl, pyrenyl, chrysene, naphtonaphthyl, and combinations thereof;
ar is selected from substituted or unsubstituted 3-to 30-membered heteroaryl, preferably furyl, thienyl, pyrrolyl, pyridyl, benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, quinazolinyl, carbazolyl, benzocarbazolyl, and combinations thereof;
Ar 1 when selected from substituted or unsubstituted 3-to 30-membered heteroaryl groups, furyl, thienyl, pyrrolyl, pyridyl, benzofuryl, etc. are preferred,Benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and combinations thereof;
R 1 、R 2 independently selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, biphenyl, naphthyl, terphenyl, and combinations thereof.
Further, ar is selected from any one of the following structures:
；
wherein, represents the site of attachment.
Still further, formula I includes the structure shown below:
；
wherein R is 3 Selected from hydrogen or phenyl.
In the above-mentioned technical scheme, the method comprises the steps of,
the substitution positions are defined as follows:
the terms "substituted or unsubstituted C6-C30 aryl", "substituted or unsubstituted 3-to 30-membered heteroaryl", "substituted or unsubstituted C1-C6 alkyl" wherein the number of carbon atoms of the aryl, heteroaryl and alkyl groups represents the number of carbon atoms constituting the unsubstituted aryl, unsubstituted alkyl, or the total number of heteroatoms and carbon atoms constituting the heteroaryl group, irrespective of the number of carbon atoms in the substituents.
The term "substituted or unsubstituted" means substituted with one, two or more substituents selected from the group consisting of: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopentane, cyclohexane, phenyl, biphenyl, naphthyl, fluorenyl, dimethylfluorenyl, phenanthryl, anthracenyl, indenyl, triphenylenyl, pyrenyl, chrysene, furanyl, thienyl, pyrrolyl, pyridyl, benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, carbazolyl, benzocarbazolyl, or a substituent linked by two or more of the substituents indicated above, or not.
Heteroaryl groups include monocyclic aromatic groups and polycyclic aromatic ring systems of at least one heteroatom including, but not limited to O, S and N.
The compounds specifically have the following structure, but are not limited thereto:
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。
the second technical purpose of the invention is to provide a preparation method of the organic light-emitting auxiliary material, which specifically comprises the following steps:
after reactant a (1.0 eq) and reactant b (1.1-1.5 eq) were completely dissolved in xylene in a round bottom flask under nitrogen protection, base (2.0-2.5 eq), palladium catalyst (0.01-0.05 eq), phosphine ligand (0.02-0.15 eq) were added thereto, and then the resultant was heated to 130-140 ℃ and stirred for 8-12 hours; filtering with diatomaceous earth while hot, cooling the filtrate to room temperature, adding water into the filtrate, washing, separating to obtain organic phase, and extracting water phase with ethyl acetate; drying the combined organic layers with magnesium sulfate and purifying by column chromatography to give formula I;
the specific synthetic route is as follows:
；
wherein, the liquid crystal display device comprises a liquid crystal display device,
hal is selected from Cl, br, I;
R 1 、R 2 、Ar、Ar 1 and n has the definition given above.
Further, the palladium catalyst is selected from Pd 2 (dba) 3 ，Pd(PPh 3 ) 4 ，PdCl 2 ，PdCl 2 (dppf)，Pd(OAc) 2 ，Pd(PPh 3 ) 2 Cl 2 Or NiCl 2 (dppf); the base is selected from K 2 CO 3 ，K 3 PO 4 ，Na 2 CO 3 ，CsF，Cs 2 CO 3 Or t-Buona, the phosphine ligand being selected from the group consisting of P (t-Bu) 3 ，X-phos，PET 3 ，PMe 3 ，PPh 3 ，KPPh 2 Or P (t-Bu) 2 Cl。
The invention also discloses application of the organic light-emitting auxiliary material in preparation of an organic electroluminescent device.
Compared with the prior art, the invention has the following beneficial effects:
compared with the prior art, the organic light-emitting auxiliary material provided by the invention ensures the space torsion of a molecular structure through arylene bridging adamantane and 9-methylfluorenyl, and avoids the phenomena of large intermolecular interaction, poor service life of devices and low light-emitting efficiency caused by molecular stacking; the molecular structure is prolonged by means of bridging, so that the mobility of molecules is improved, and hole transport is facilitated; meanwhile, the HOMO energy level of the molecule can be regulated and controlled by selecting different aryl groups or heteroaryl groups (-Ar part) in the aromatic amine structure, so that the material is suitable for different device collocations.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings that are required to be used in the embodiments or the description of the prior art will be briefly described below, and it is obvious that the drawings in the following description are only embodiments of the present invention, and that other drawings can be obtained according to the provided drawings without inventive effort for a person skilled in the art.
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of compound 17 in example 1.
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of the compound 85 in example 2.
FIG. 3 is a nuclear magnetic resonance hydrogen spectrum of compound 175 in example 3.
FIG. 4 is a nuclear magnetic resonance hydrogen spectrum of compound 254 in example 4.
FIG. 5 is a nuclear magnetic resonance hydrogen spectrum of compound 269 in example 5.
Detailed Description
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1: synthesis of Compound 17
；
After complete dissolution of reactant a-17 (20 mmol, CAS: 60253-06-7) and reactant b-17 (25 mmol, CAS: 2568936-38-7) in xylene (200 mL) under nitrogen, sodium tert-butoxide (45 mmol), bis (tri-tert-butylphosphine) palladium (0.5 mmol), tri-tert-butylphosphine (1.0 mmol) were added to it, and the resultant was heated to 135℃and stirred for 10 hours. Filtering with diatomaceous earth while hot, cooling the filtrate to room temperature, adding water into the filtrate, washing, separating to obtain organic phase, and extracting water phase with ethyl acetate; the combined organic layers were then dried over magnesium sulfate and purified by column chromatography to give compound 17. (9.26 g, yield: 73%, test value MS (ESI, M/Z): [ M+H ]] + = 634.01）。
The nuclear magnetic resonance hydrogen spectrum of compound 17 is shown in fig. 1.
Characterization:
HPLC purity: > 99.8%.
Elemental analysis:
theoretical value: c, 90.95, H, 6.84, N, 2.21
Test value: c, 90.85, H, 6.92, N, 2.26.
Example 2: synthesis of Compound 85
；
After complete dissolution of reactant a-85 (20 mmol, CAS: 2128245-45-2) and reactant b-85 (25 mmol, CAS: 2735729-50-5) in xylene (200 mL) under nitrogen, sodium t-butoxide (45 mmol), bis (tri-t-butylphosphine) palladium (0.5 mmol), tri-t-butylphosphine (1.0 mmol) were added to it, and the resultant was heated to 135℃and stirred for 10 hours. Filtering with diatomaceous earth while hot, cooling the filtrate to room temperature, adding water into the filtrate, washing, separating to obtain organic phase, and extracting water phase with ethyl acetate; then dried and combined using magnesium sulfateThe organic layer was then purified by column chromatography to give compound 85. (10.24 g, yield: 76%, test value MS (ESI, M/Z): [ M+H ]] + = 674.09）。
The nuclear magnetic resonance hydrogen spectrum of compound 85 is shown in fig. 2.
Characterization:
HPLC purity: > 99.8%.
Elemental analysis:
theoretical value: c, 90.89; H, 7.03; N, 2.08
Test value: c, 90.84, H, 7.09, N, 2.12.
Example 3: synthesis of Compound 175
；
After complete dissolution of reactant a-17 (20 mmol) and reactant b-175 (25 mmol, CAS: 2799914-45-7) in xylene (200 mL) under nitrogen, sodium tert-butoxide (45 mmol), bis (tri-tert-butylphosphine) palladium (0.5 mmol), tri-tert-butylphosphine (1.0 mmol) were added thereto, and the resultant was heated to 135℃and stirred for 10 hours. Filtering with diatomaceous earth while hot, cooling the filtrate to room temperature, adding water into the filtrate, washing, separating to obtain organic phase, and extracting water phase with ethyl acetate; the combined organic layers were then dried over magnesium sulfate and purified by column chromatography to give compound 175. (12.01 g, yield: 79%, test value MS (ESI, M/Z): [ M+H ]] + = 760.19）。
The nuclear magnetic resonance hydrogen spectrum of compound 175 is shown in fig. 3.
Characterization:
HPLC purity: > 99.8%.
Elemental analysis:
theoretical value: c, 91.66, H, 6.50, N, 1.84
Test value: c, 91.59, H, 6.58, N, 1.89.
Example 4: synthesis of Compound 254
；
After reactants a-254 (20 mmol, CAS: 2836298-17-8) and b-254 (25 mmol, CAS: 2759914-44-6) were completely dissolved in xylene (200 mL) in a round bottom flask under nitrogen, sodium t-butoxide (45 mmol), bis (tri-t-butylphosphine) palladium (0.5 mmol), tri-t-butylphosphine (1.0 mmol) were added thereto, and the resultant was heated to 135℃and stirred for 10 hours. Filtering with diatomaceous earth while hot, cooling the filtrate to room temperature, adding water into the filtrate, washing, separating to obtain organic phase, and extracting water phase with ethyl acetate; the combined organic layers were then dried over magnesium sulfate and purified by column chromatography to give compound 254. (10.37 g, yield: 67%, test value MS (ESI, M/Z): [ M+H ]] + =774.20）。
The nuclear magnetic resonance hydrogen spectrum of compound 254 is shown in fig. 4.
Characterization:
HPLC purity: > 99.8%.
Elemental analysis:
theoretical value: c, 91.55, H, 6.64, N, 1.81
Test value: c, 91.46, H, 6.72, N, 1.85.
Example 5: synthesis of Compound 269
；
After complete dissolution of reactant a-254 (20 mmol) and reactant b-269 (25 mmol, CAS: 2412489-63-3) in xylene (200 mL) under nitrogen, sodium tert-butoxide (45 mmol), bis (tri-tert-butylphosphine) palladium (0.5 mmol), tri-tert-butylphosphine (1.0 mmol) were added thereto, and the resultant was heated to 135℃and stirred for 10 hours. Filtering with diatomaceous earth while hot, cooling the filtrate to room temperature, adding water into the filtrate, washing, separating to obtain organic phase, and extracting water phase with ethyl acetate; the combined organic layers were then dried over magnesium sulfate and purified by column chromatography to give the compound269. (9.77 g, yield: 71%, test value MS (ESI, M/Z): [ M+H ]] + =688.10）。
The nuclear magnetic resonance hydrogen spectrum of compound 269 is shown in FIG. 5.
Characterization:
HPLC purity: > 99.8%.
Elemental analysis:
theoretical value: c, 90.78, H, 7.18, N, 2.04
Test value: c, 90.68, H, 7.27, N, 2.08.
Examples 6 to 75
The synthesis of the following compounds, whose molecular formulas and mass spectra are shown in table 1 below, was accomplished with reference to the synthesis methods of examples 1 to 5.
Table 1 molecular formula and mass spectrum
Examples Compounds of formula (I) Molecular formula Mass spectrometry test values
Example 6 6 C 48 H 43 N 634.01
Example 7 10 C 43 H 41 N 571.92
Example 8 13 C 48 H 43 N 633.99
Example 9 14 C 48 H 43 N 634.02
Example 10 16 C 54 H 47 N 710.11
Example 11 19 C 54 H 47 N 710.12
Example 12 20 C 54 H 47 N 710.11
Example 13 22 C 54 H 47 N 710.13
Example 14 36 C 52 H 45 N 684.07
Example 15 38 C 48 H 41 NO 648.02
Example 16 40 C 51 H 47 N 674.06
Example 17 41 C 48 H 41 NO 648.01
Example 18 43 C 54 H 46 N 2 723.19
Example 19 46 C 54 H 46 N 2 723.17
Example 20 48 C 57 H 51 N 750.17
Example 21 50 C 57 H 51 N 750.15
Example 22 53 C 54 H 45 NS 740.20
Example 23 56 C 54 H 45 NS 740.19
Example 24 57 C 54 H 45 NO 724.11
Example 25 58 C 54 H 45 NO 724.13
Example 26 66 C 54 H 46 N 2 723.21
Example 27 67 C 57 H 51 N 750.17
Example 28 69 C 54 H 45 NO 724.11
Example 29 70 C 54 H 45 NO 724.14
Example 30 72 C 54 H 45 NO 724.12
Example 31 73 C 54 H 45 NO 724.10
Example 32 80 C 54 H 47 N 710.12
Example 33 81 C 54 H 47 N 710.10
Example 34 82 C 54 H 47 N 710.09
Example 35 87 C 58 H 49 N 760.15
Example 36 90 C 60 H 49 NO 800.24
Example 37 97 C 60 H 50 N 2 799.29
Example 38 100 C 60 H 50 N 2 799.28
Example 39 108 C 58 H 49 N 760.16
Example 40 111 C 58 H 49 N 760.15
Example 41 118 C 57 H 51 N 750.19
Example 42 119 C 57 H 51 N 750.16
Example 43 126 C 60 H 49 NS 816.28
Example 44 129 C 60 H 49 NO 800.23
Example 45 167 C 64 H 51 NO 850.27
Example 46 173 C 58 H 49 N 760.18
Example 47 178 C 57 H 51 N 750.17
Example 48 179 C 57 H 51 N 750.17
Example 49 197 C 63 H 55 N 826.28
Example 50 203 C 60 H 49 NO 800.24
Example 51 211 C 56 H 47 N 734.12
Example 52 216 C 49 H 45 N 648.04
Example 53 219 C 60 H 49 NO 800.24
Example 54 220 C 67 H 55 N 874.31
Example 55 226 C 66 H 53 NO 876.32
Example 56 228 C 60 H 51 N 786.19
Example 57 242 C 51 H 47 N 674.08
Example 58 243 C 52 H 49 N 688.10
Example 59 244 C 55 H 48 N 2 737.24
Example 60 250 C 58 H 53 N 764.20
Example 61 251 C 58 H 53 N 764.24
Example 62 252 C 58 H 53 N 764.21
Example 63 253 C 59 H 51 N 774.21
Example 64 258 C 58 H 53 N 764.24
Example 65 259 C 58 H 53 N 764.23
Example 66 262 C 55 H 47 NO 738.20
Example 67 263 C 52 H 49 N 688.13
Example 68 264 C 61 H 51 NS 830.34
Example 69 267 C 52 H 49 N 688.12
Example 70 268 C 66 H 59 N 866.35
Example 71 269 C 52 H 49 N 688.11
Example 72 270 C 66 H 59 N 866.36
Example 73 274 C 52 H 49 N 688.13
Example 74 277 C 58 H 53 N 764.25
Example 75 278 C 56 H 49 NO 752.21
In addition, it should be noted that the mass spectrometer model in the embodiment of the invention is a Waters XEVO TQD, low-precision, and tested with ESI source; other compounds of the present invention can be obtained by referring to the synthetic methods of the above-listed examples, and are not exemplified herein.
The invention provides an organic electroluminescent device, which specifically can comprise a hole injection layer, a hole transmission layer, an electron blocking layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transmission layer, an electron injection layer, a cap layer and the like as structures of organic layers. In one embodiment, the organic light emitting element may be described as an "organic layer" disposed between the cathode and the anode, which may be achieved by combining the above layers, or some layers may be omitted or added entirely.
According to one embodiment of the present specification, the compound of formula I prepared according to the present invention is used as a light-emitting auxiliary layer material.
The anode is made of a conductor such as a metal, metal oxide, and/or conductive polymer that has a higher work function to aid in hole injection. The metal can be nickel, platinum, vanadium, chromium, copper, zinc, gold, silver or alloys thereof; the metal oxide can be zinc oxide, indium Tin Oxide (ITO) or indium zinc oxide; the combination of metal and oxide can be ZnO and A1 or SnO 2 Sb or ITO and Ag; the conductive polymer may be selected from poly (3-methylthiophene), poly (3, 4- (ethylene-1, 2-dioxy) thiophene), polypyrrole, and polyaniline, but is not limited thereto.
The hole injection layer and the hole transport layer efficiently inject or transport holes from the anode between the electrodes to which an electric field has been applied, and preferably have high hole injection efficiency and efficiently transport the injected holes. Therefore, a substance having a small ionization potential, a large hole mobility, and excellent stability, and which is less likely to cause impurities that become traps during production and use, is preferable. The hole injection layer is preferably a p-doped hole injection layer; the hole transport material may be selected from arylamine derivatives, conductive polymers, block copolymers having both conjugated and non-conjugated portions, and the like.
A light-emitting auxiliary layer (multi-layer hole transporting layer) is interposed between the hole transporting layer and the light-emitting layer, and functions to smoothly move holes from the anode to the light-emitting layer and block electrons from the cathode.
The light-emitting layer is preferably a compound which emits light by excitation by recombination of holes and electrons, and is preferably a compound which can form a stable thin film shape and exhibits high light-emitting efficiency in a solid state. The light emitting layer may be a single layer or multiple layers and may include a host material and a dopant material. The amounts of the host material and the dopant material to be used may be determined in accordance with the respective material characteristics. The doping method may be realized by co-evaporation with the host material, or may be formed by simultaneous evaporation after mixing with the host material.
The electron transport layer and the electron injection layer efficiently transport or inject electrons from the anode and cathode between the electrodes to which an electric field has been applied. An impurity substance which has a large electron affinity, a large electron mobility, and excellent stability and is not likely to cause a trap is preferable.
The anode is a substance capable of injecting electrons with good efficiency, and the same material as that of the anode can be selected. If a low work function metal is chosen that facilitates efficient electron injection, it is often necessary to dope trace amounts of lithium, cesium or magnesium to avoid its instability in the atmosphere.
There are no particular restrictions on other layer materials in an OLED device, except that the light-emitting auxiliary layer disclosed herein comprises formula I.
The organic electroluminescent composition and the organic electroluminescent device according to the present invention are described in detail below with reference to specific examples.
Device example 1 preparation of Red organic electroluminescent device
a. ITO anode: washing ITO (indium tin oxide) -Ag-ITO (indium tin oxide) glass substrate with the coating thickness of 150nm in distilled water for 2 times, washing with ultrasonic waves for 30min, washing with distilled water for 2 times repeatedly, washing with ultrasonic waves for 10min, baking with a vacuum oven at 220 ℃ for 2 hours after washing, and cooling after baking is finished, so that the glass substrate can be used. The substrate is used as an anode, a vapor deposition device process is performed by using a vapor deposition machine, and other functional layers are sequentially vapor deposited on the substrate.
b. HIL (hole injection layer): vacuum evaporation of hole injection layer materials HT-1 and P-dock at an evaporation rate of 1 Å/s, wherein the evaporation rate ratio of HT-1 to P-dock is 97:3, the thickness is 10nm.
c. HTL (hole transport layer): 130nm of HT-1 was vacuum deposited as a hole transport layer on top of the hole injection layer at a deposition rate of 1.5 Å/s.
d. Prime (light-emitting auxiliary layer): the compound 10 of the present invention was vacuum-deposited as a light-emitting auxiliary layer on top of the hole transport layer at a deposition rate of 0.5 Å/s at 80 nm.
e. EML (light emitting layer): then, on the above light-emitting auxiliary layer, a Host material (Host-1) and a Dopant material (Dopant-1) having a thickness of 40nm were vacuum-evaporated as light-emitting layers at an evaporation rate of 1 Å/s, wherein the evaporation rate ratio of Host-1 to Dopant-1 was 97:3.
f. HB (hole blocking layer): HB-1 hole blocking layer with a thickness of 5.0nm was vacuum deposited at a deposition rate of 0.5. 0.5 Å/s.
g. ETL (electron transport layer): ET-1 and Liq with the thickness of 30nm are vacuum evaporated as electron transport layers at an evaporation rate of 1 Å/s. Wherein the ratio of the evaporation rates of ET-1 and Liq is 50:50.
h. EIL (electron injection layer): an electron injection layer was formed by vapor deposition of 1.0nm on a Yb film layer at a vapor deposition rate of 0.5. 0.5 Å/s.
i. And (3) cathode: and evaporating magnesium and silver at a deposition rate ratio of 1 Å/s of 13nm, wherein the deposition rate ratio is 1:9, so as to obtain the OLED device.
j. Light extraction layer: CPL-1 having a thickness of 65nm was vacuum deposited as a light extraction layer on the cathode at a deposition rate of 1 Å/s.
k. And packaging the substrate subjected to evaporation. Firstly, a gluing device is adopted to carry out a coating process on a cleaned cover plate by UV glue, then the coated cover plate is moved to a lamination working section, a substrate subjected to vapor deposition is placed at the upper end of the cover plate, and finally the substrate and the cover plate are bonded under the action of a bonding device, and meanwhile, the UV glue is cured by illumination.
The device structure is as follows:
ITO/Ag/ITO/HT-1:P-split (10 nm)/HT-1 (130 nm)/prime (compound of the invention) (10 nm)/Host-1:Dosplit-1 (40 nm)/HB-1 (5 nm)/ET-1:Liq (30 nm)/Yb (1 nm)/Mg:Ag (13 nm)/CPL-1 (65 nm).
The structural formula of the compound in the device is as follows:
。
referring to the method provided in the above device example 1, compounds 13, 14, 16, 17, 19, 20, 22, 36, 38, 40, 41, 43, 46, 48, 50, 53, 56, 57, 66, 69, 70, 72, 73, 82, 85, 97, 100, 111, 118, 119, 126, 175, 179, 211, 216, 219, 242, 243, 244, 250, 251, 258, 264, 269, 274, 277 were selected respectively instead of compound 10, evaporation of the light-emitting auxiliary layer was performed, and corresponding organic electroluminescent devices, which were respectively denoted as device examples 2 to 47, were prepared.
Device comparative examples 1-7:
the organic electroluminescent devices of comparative examples 1 to 7 were prepared according to the above-described preparation method of an organic electroluminescent device, except that: the compound 10 in application example 1 was replaced with the comparative compounds 1 to 7, respectively, to form a light-emitting auxiliary layer. Wherein, the structural formula of the comparative compounds 1-7 is as follows:
。
the organic electroluminescent devices obtained in the above device examples 1 to 47 and device comparative examples 1 to 7 were characterized in terms of driving voltage, luminous efficiency and lifetime at 6000 (nits) luminance, and the test results are shown in table 2 below:
TABLE 2
Organic electroluminescent device Luminescent auxiliary material Driving voltage (V) Luminous efficiency (cd/A) CIEx CIEy T95 life (h)
Comparative example 1 Comparative Compound 1 3.55 54.15 0.686 0.313 1456
Comparative example 2 Comparative Compound 2 3.58 54.87 0.685 0.314 1467
Comparative example 3 Comparative Compound 3 3.56 55.78 0.687 0.312 1471
Comparative example 4 Comparative Compound 4 3.64 53.33 0.686 0.313 1465
Comparative example 5 Comparative Compound 5 3.57 53.61 0.687 0.312 1458
Comparative example 6 Comparative Compound 6 3.60 52.46 0.686 0.313 1464
Comparative example 7 Comparative Compound 7 3.55 53.94 0.685 0.314 1459
Device example 1 10 3.52 57.64 0.686 0.313 1568
Device example 2 13 3.48 59.05 0.685 0.314 1609
Device example 3 14 3.50 58.87 0.686 0.313 1603
Device example 4 16 3.49 57.86 0.685 0.314 1584
Device example 5 17 3.48 57.53 0.687 0.312 1579
Device example 6 19 3.51 59.21 0.687 0.312 1596
Device example 7 20 3.49 59.61 0.685 0.314 1581
Device example 8 22 3.52 58.96 0.685 0.314 1600
Device example 9 36 3.53 59 0.687 0.312 1579
Device example 10 38 3.51 58.81 0.686 0.313 1580
Device example 11 40 3.50 57.97 0.685 0.314 1574
Device example 12 41 3.48 58.27 0.686 0.313 1586
Device example 13 43 3.50 57.92 0.685 0.314 1579
Device example 14 46 3.48 58.44 0.686 0.313 1585
Device example 15 48 3.52 59 0.687 0.312 1569
Device example 16 50 3.50 58.96 0.685 0.314 1573
Device example 17 53 3.49 57.47 0.686 0.313 1564
Device example 18 56 3.51 57.93 0.685 0.314 1570
Device example 19 57 3.48 58.82 0.686 0.313 1581
Device example 20 66 3.48 58.78 0.685 0.314 1587
Device example 21 69 3.50 58.01 0.687 0.312 1568
Device example 22 70 3.53 58.17 0.685 0.314 1577
Device example 23 72 3.49 58.26 0.687 0.312 1585
Device example 24 73 3.48 59.21 0.685 0.314 1571
Device example 25 82 3.51 57.14 0.686 0.313 1556
Device example 26 85 3.53 58.09 0.686 0.313 1570
Device example 27 97 3.48 57.37 0.685 0.314 1566
Device example 28 100 3.50 57.44 0.685 0.314 1551
Device example 29 111 3.49 58.73 0.686 0.313 1573
Device example 30 118 3.51 57.93 0.686 0.313 1593
Device example 31 119 3.48 58.23 0.685 0.314 1587
Device example 32 126 3.52 57.36 0.685 0.314 1575
Device example 33 175 3.51 58.67 0.687 0.312 1584
Device example 34 179 3.48 58.78 0.685 0.314 1591
Device example 35 211 3.49 58.39 0.685 0.314 1569
Device example 36 216 3.53 57.26 0.686 0.313 1570
Device example 37 219 3.48 57.91 0.687 0.312 1569
Device example 38 242 3.49 58.77 0.685 0.314 1609
Device example 39 243 3.48 59.57 0.686 0.313 1623
Device example 40 244 3.51 57.26 0.685 0.314 1581
Device example 41 250 3.49 59.64 0.658 0.341 1612
Device example 42 251 3.50 59.13 0.686 0.313 1607
Device example 43 258 3.48 59.67 0.658 0.341 1617
Device example 44 264 3.52 58.01 0.687 0.312 1584
Device example 45 269 3.48 59.59 0.685 0.314 1620
Device example 46 274 3.50 57.99 0.686 0.313 1583
Device example 47 277 3.52 57.73 0.686 0.313 1579
As can be seen from table 2, the red OLED devices prepared using the organic light-emitting auxiliary materials provided by the present invention are superior in terms of lifetime of devices in examples 1 to 47 compared with the conventional OLED devices provided by comparative examples 1 to 7, and the series structures according to the general formula of the present invention are increased by 80h to 167h compared with the comparative examples, and the luminous efficiency is improved by 2.44% to 13.74% compared with the comparative examples. At the same time, the compounds according to the general formula of the invention are also improved in terms of the drive voltage relative to the comparative examples.
In particular, the method comprises the steps of,
。
wherein, the structure of the comparative compound 1 is similar to that of the compound 13 in the embodiment provided by the invention, and two substituent groups in triarylamine are the same, the difference is that the comparative compound 1 is bridged with 9-phenylfluorenyl through 9, 9-dimethylfluorenyl, and the compound 13 in the invention is bridged with 9-methylfluorenyl through phenylene. Since 9, 9-dimethylfluorene at the bridging site is less susceptible to breakage at high temperature than phenylene in compound 13 is stable, the prepared OLED device is susceptible to crystallization at high temperature, resulting in serious decrease in light-emitting efficiency and lifetime, and increase in driving voltage. As can be seen from table 2, the driving voltage of compound 13 was reduced by 0.07eV, the device lifetime was increased by 153h, and the luminous efficiency was improved by 4.90cd/a, relative to comparative compound 1.
Wherein, the structure of the comparative compound 2 is similar to that of the compound 13 in the embodiment provided by the invention, and two substituent groups in the triarylamine are the same and both comprise rigid adamantane structures with larger steric hindrance. The difference is that the compound 13 is bridged by phenylene, the aromatic amine and the 9-methylfluorenyl are bonded at the para position of the phenylene, the comparative compound 2 is bridged by naphthalene, the 9, 9-dimethylfluorenyl and the aromatic amine are bonded at the ortho position of the naphthyl, and the bonding at the ortho position leads to the excessive torsion of the overall space configuration of the comparative compound 2, so that a carrier trap is easy to form in a device prepared by the compound, the transmission performance of holes is poor, the luminous efficiency of the device is reduced, and the driving voltage is increased.
。
Wherein the comparative compound 3 has a structure similar to that of the compound 22 in the examples provided by the present invention, except that the compound 22 is bonded to the 9-position of the fluorenyl group via the phenylene group, which is sp 3 The hybridization breaks the symmetry of the configuration, while the comparative compound 3 is bonded on the benzene ring of the 9, 9-dimethylfluorenyl group, so that the overall symmetry of the molecular configuration is better than that of the compound 22, thereby leading to easy crystallinity of the material, poor film forming property and reduced service life of the device.
。
The structure of the comparative compound 5 is similar to that of the compound 70 in the example provided by the invention, except that adamantane in the compound 70 is bonded to the aromatic amine through phenylene, and the comparative compound 5 is formed by bonding the benzene ring part of 9, 9-dimethylfluorenyl to the aromatic amine. Adamantane in the compound 70 has space stereoscopicity, the molecular space configuration is optimized by further connecting through phenylene in order to avoid excessive torsion, and the benzene ring of 9, 9-dimethylfluorenyl is not connected with aromatic amine through phenylene or other groups in the comparative compound 5, so that the configuration is excessively torsion, and the modeling of the material is poor; and the rigidity of adamantane also makes the energy loss that leads to because of molecular self motion reduce to improve the heat resistance of molecule, make the life-span of obtained device longer.
Device example 48 preparation of Green organic electroluminescent device
a. ITO anode: washing ITO (indium tin oxide) -Ag-ITO (indium tin oxide) glass substrate with the coating thickness of 150nm in distilled water for 2 times, washing with ultrasonic waves for 30min, washing with distilled water for 2 times repeatedly, washing with ultrasonic waves for 10min, baking with a vacuum oven at 220 ℃ for 2 hours after washing, and cooling after baking is finished, so that the glass substrate can be used. The substrate is used as an anode, a vapor deposition device process is performed by using a vapor deposition machine, and other functional layers are sequentially vapor deposited on the substrate.
b. HIL (hole injection layer): vacuum evaporation of the hole injection layer materials HT-2 and P-dock at an evaporation rate of 1 Å/s, wherein the evaporation rate ratio of HT-2 to P-dock is 97:3, the thickness is 10nm.
c. HTL (hole transport layer): 130nm of HT-2 was vacuum deposited as a hole transport layer on top of the hole injection layer at a deposition rate of 1.5 Å/s.
d. Prime (light-emitting auxiliary layer): the compound 6 of the present invention was vacuum-deposited as a light-emitting auxiliary layer on top of the hole transport layer at a deposition rate of 0.5 Å/s at 35 nm.
e. EML (light emitting layer): then, on the above light-emitting auxiliary layer, a double-Host material (Host-2 and Host-3) and a Dopant material (Dopant-2) having a thickness of 30nm were vacuum-evaporated as light-emitting layers at an evaporation rate of 1 Å/s, wherein Host-2 and Host-3 were 50:50. Wherein the evaporation rate ratio of the double-body material to the Dopant-2 is 98:2.
f. HB (hole blocking layer): HB-2 hole blocking layer with thickness of 5.0nm was vacuum evaporated at an evaporation rate of 0.5. 0.5 Å/s.
g. ETL (electron transport layer): ET-2 and Liq with the thickness of 30nm are vacuum evaporated as electron transport layers at an evaporation rate of 1 Å/s. Wherein the ratio of the evaporation rates of ET-2 and Liq is 50:50.
h. EIL (electron injection layer): an electron injection layer was formed by vapor deposition of 1.0nm on a Yb film layer at a vapor deposition rate of 0.5. 0.5 Å/s.
i. And (3) cathode: and evaporating magnesium and silver at a deposition rate ratio of 1 Å/s of 13nm, wherein the deposition rate ratio is 1:9, so as to obtain the OLED device.
j. Light extraction layer: CPL-2 having a thickness of 70nm was vacuum deposited on the cathode at a deposition rate of 1 Å/s as a light extraction layer.
k. And packaging the substrate subjected to evaporation. Firstly, a gluing device is adopted to carry out a coating process on a cleaned cover plate by UV glue, then the coated cover plate is moved to a lamination working section, a substrate subjected to vapor deposition is placed at the upper end of the cover plate, and finally the substrate and the cover plate are bonded under the action of a bonding device, and meanwhile, the UV glue is cured by illumination.
The device structure is as follows:
ITO/Ag/ITO/HT-2:P-dose (10 nm)/HT-2 (130 nm)/prime (compound of the invention) (35 nm)/Host-2:host-3:dose-2 (30 nm)/HB-2 (5 nm)/ET-2:Liq (30 nm)/Yb (1 nm)/Mg:Ag (13 nm)/CPL-2 (70 nm). The structural formula of the compound in the device is as follows:
。
referring to the method provided in the above device example 48, compounds 13, 14, 16, 19, 20, 38, 40, 41, 43, 46, 48, 50, 53, 56, 57, 58, 67, 69, 73, 80, 81, 87, 90, 108, 118, 119, 129, 167, 173, 178, 179, 197, 203, 220, 226, 228, 243, 250, 252, 253, 259, 262, 267, 268, 269, 278 were selected respectively instead of compound 6, evaporation of the light-emitting auxiliary layer was performed, and corresponding organic electroluminescent devices, which were respectively denoted as device examples 48 to 94, were prepared.
Device comparative examples 8-14:
the organic electroluminescent devices of comparative examples 8 to 14 were prepared according to the above-described preparation method of an organic electroluminescent device, except that the compound 6 of application example 48 was replaced with the comparative compounds 8 to 14, respectively, to form a light-emitting auxiliary layer. Wherein, the structural formula of the comparative compounds 8-14 is as follows:
。
the organic electroluminescent devices obtained in the above device examples 48 to 94 and device comparative examples 8 to 14 were characterized in terms of driving voltage, luminous efficiency and lifetime at 15000 (nits) luminance, and the test results are shown in table 3 below:
TABLE 3 Table 3
Organic electroluminescent device Luminescent auxiliary material Driving voltage (V) Luminous efficiency (cd/A) CIEx CIEy T95 life (h)
Comparative example 8 Comparative Compound 1 3.76 157.3 0.246 0.716 840
Comparative example 9 Comparative Compound 2 3.78 155.3 0.243 0.719 842
Comparative example 10 Comparative Compound 3 3.74 158.3 0.245 0.717 856
Comparative example 11 Comparative Compound 4 3.77 155.3 0.245 0.717 839
Comparative example 12 Comparative Compound 5 3.77 155.3 0.243 0.719 843
Comparative example 13 Comparative Compound 6 3.81 155.9 0.246 0.716 856
Comparative example 14 Comparative Compound 7 3.79 155.9 0.245 0.717 852
Device example 48 6 3.63 163.6 0.244 0.718 898
Device example 49 13 3.54 166.7 0.246 0.716 939
Device example 50 14 3.57 166.7 0.246 0.716 937
Device example 51 16 3.55 163.1 0.243 0.719 939
Device example 52 19 3.58 164.7 0.245 0.717 932
Device example 53 20 3.57 166.5 0.246 0.716 940
Device example 54 38 3.60 164.2 0.243 0.719 936
Device example 55 40 3.59 165.3 0.246 0.716 934
Device example 56 41 3.61 165.5 0.245 0.717 937
Device example 57 43 3.59 163.1 0.245 0.717 925
Device example 58 46 3.57 163.7 0.243 0.719 939
Device example 59 48 3.60 163.9 0.243 0.719 921
Device example 60 50 3.59 165.1 0.244 0.718 932
Device example 61 53 3.64 164.3 0.245 0.717 915
Device example 62 56 3.61 165.0 0.243 0.719 920
Device example 63 57 3.57 164.6 0.244 0.718 902
Device example 64 58 3.64 164.9 0.245 0.717 907
Device example 65 67 3.57 165.3 0.245 0.717 917
Device example 66 69 3.61 165.9 0.243 0.719 921
Device example 67 73 3.60 166.1 0.246 0.716 914
Device example 68 80 3.57 167.1 0.244 0.718 900
Device example 69 81 3.65 162.8 0.245 0.717 935
Device example 70 87 3.61 163.3 0.243 0.719 935
Device example 71 90 3.67 163.9 0.244 0.718 897
Device example 72 108 3.64 164.9 0.245 0.717 918
Device example 73 118 3.60 164.1 0.244 0.718 939
Device example 74 119 3.59 165.0 0.244 0.718 931
Device example 75 129 3.66 163.0 0.245 0.717 914
Device example 76 167 3.67 162.3 0.245 0.717 899
Device example 77 173 3.56 165.9 0.243 0.719 906
Device example 78 178 3.59 165.0 0.244 0.718 938
Device example 79 179 3.54 163.9 0.245 0.717 941
Device example 80 197 3.61 164.6 0.246 0.716 919
Device example 81 203 3.58 165.8 0.245 0.717 902
Device example 82 220 3.64 166.0 0.246 0.716 897
Device example 83 226 3.67 164.7 0.243 0.719 919
Device example 84 228 3.66 164.3 0.244 0.718 911
Device example 85 243 3.55 169.9 0.245 0.717 949
Device example 86 250 3.54 165.4 0.244 0.718 946
Device example 87 252 3.55 165.7 0.244 0.718 944
Device example 88 253 3.61 165.9 0.243 0.719 929
Device example 89 259 3.56 167.2 0.246 0.716 948
Device example 90 262 3.61 164.8 0.244 0.718 930
Device example 91 267 3.57 163.7 0.245 0.717 938
Device example 92 268 3.56 166.1 0.244 0.718 936
Device example 93 269 3.54 167.0 0.246 0.716 954
Device example 94 278 3.59 165.6 0.245 0.717 919
As can be seen from Table 3, the green OLED devices prepared using the organic light-emitting auxiliary materials provided in the examples 48 to 94 of the present invention are superior to the conventional OLED devices provided in comparative examples 8 to 14 in terms of the lifetime of the devices, and the series structures according to the general formula of the present invention are improved by 41h to 115h as compared with the comparative examples, and the luminous efficiency is increased by 2.53% to 7.66% as compared with the comparative examples. At the same time, the compounds according to the general formula of the invention are also improved in terms of the drive voltage relative to the comparative examples.
In particular, the method comprises the steps of,
。
the structure of the comparative compound 6 is similar to that of the compound 178 in the embodiment provided by the invention, the difference is that 9-methylfluorenyl and aromatic amine in the compound 178 are bridged through phenylene, spirobifluorenyl and aromatic amine in the compound 6 are directly bonded, and compared with the compound 178, the comparative compound has two groups (adamantyl and spirobifluorenyl) with high rigidity and steric hindrance, so that the configuration is too large in torsion and poor in fluidity, carrier traps are easy to form, and the compound 178 is prolonged in system and enhanced in molecular fluidity through buffering of phenylene, so that the luminous efficiency of the device is improved.
。
Wherein, the structure of the comparison compound 7 is similar to that of the compound 228 in the embodiment provided by the invention, the aromatic amine in the comparison compound 7 is bonded on the benzene ring of the fluorene ring of the 9-methyl-9-phenyl fluorenyl, the aromatic amine of the compound 228 is bonded at the para position of the 9-phenyl of the 9-methyl-9-phenyl fluorenyl, the comparison compound 7 provides a larger conjugated surface, the compound 228 provides conjugation by utilizing the 9-phenyl of the 9-methyl-9-phenyl fluorenyl, the hole transmission is ensured, and meanwhile, the bonding mode of the compound 228 can prolong the molecular structure, the molecular mobility is enhanced, and the luminous efficiency is more beneficial to being improved. And secondly, the bonding adamantane position of the comparative compound 7 is 2, compared with the bonding of the compound 228 at 1, the stability is weak, the decomposition is easy in the molecular evaporation process, and the service life of the device is short.
In conclusion, the luminescent auxiliary material provided by the invention is optimized on the basis of aromatic amine with stronger electron donating ability, and through arylene bridging adamantane and 9-methylfluorenyl, the space torsion of a molecular structure can be ensured, and the phenomena of large intermolecular interaction, poor service life of a device and low luminous efficiency caused by molecular stacking are avoided; the molecular structure can be prolonged by means of bridging, the mobility of the molecules is improved, and the hole transport is facilitated; meanwhile, the HOMO energy level of the molecule can be regulated by selecting different aryl or heteroaryl in the aromatic amine, so that the material is suitable for different device collocations. From the data in tables 2 and 3, it is also known that the compounds according to the general formula of the present invention are excellent in device aspects, particularly in device lifetime and light-emitting efficiency emission, regardless of whether they are red or green devices, and that the driving voltage is improved.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims (8)

1. An organic light-emitting auxiliary material is characterized by having a structure shown in a formula I:
wherein, the liquid crystal display device comprises a liquid crystal display device,
ar is selected from unsubstituted C6-C30 aryl or unsubstituted 3-to 30-membered heteroaryl; the heteroatom in the heteroaryl group is selected from O, S, N;
Ar 1 selected from hydrogen, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, dimethylfluorenyl;
R 1 、R 2 independently selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl;
n is 1 or 2.
2. The organic light-emitting auxiliary material according to claim 1, wherein,
ar is selected from unsubstituted C6-C30 aryl; in particular phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, benzofluorenyl, phenanthryl, anthracenyl, indenyl, triphenylenyl, pyrenyl, and,A group, a naphto-naphthyl group, and combinations thereof;
or Ar is selected from unsubstituted 3-to 30-membered heteroaryl; specifically, the compound is selected from furyl, thienyl, pyrrolyl, pyridyl, benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, quinazolinyl, carbazolyl, and benzocarbazolyl, and combinations thereof.
3. An organic light-emitting auxiliary material is characterized by having a structure shown in a formula I:
wherein, the liquid crystal display device comprises a liquid crystal display device,
ar is selected from any one of the following structures:
* Represents a ligation site;
Ar 1 selected from hydrogen, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, dimethylfluorenyl; r is R 1 、R 2 Independently selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl;
n is 1 or 2.
4. An organic light emitting auxiliary material according to claim 3, wherein formula I comprises the structure shown below:
wherein R is 3 Selected from hydrogen or phenyl.
5. An organic light-emitting auxiliary material, characterized in that the organic light-emitting auxiliary material is selected from any one of compounds shown in the following structural formulas:
/>
6. a method for preparing an organic light-emitting auxiliary material according to claim 1, comprising the steps of:
under the protection of nitrogen, the reactant a and the reactant b are completely dissolved in dimethylbenzene, then alkali, palladium catalyst and phosphine ligand are added, and then the mixture is heated to 130-140 ℃ and stirred for 8-12 hours for reaction; after the reaction is finished, using diatomite to carry out suction filtration while the reaction is hot, cooling the filtrate to room temperature, then adding water into the filtrate to wash, separating liquid, retaining an organic phase, and extracting an aqueous phase with ethyl acetate; drying the combined organic layers with magnesium sulfate and purifying by column chromatography to give formula I;
the specific synthetic route is as follows:
wherein, the liquid crystal display device comprises a liquid crystal display device,
hal is selected from Cl, br, I;
R 1 、R 2 、Ar、Ar 1 and n has the definition as defined in claim 1.
7. The method for producing an organic light-emitting auxiliary material according to claim 6, wherein the palladium catalyst is selected from Pd 2 (dba) 3 ，Pd(PPh 3 ) 4 ，PdCl 2 ，PdCl 2 (dppf)，Pd(OAc) 2 ，Pd(PPh 3 ) 2 Cl 2 Or NiCl 2 (dppf); the base is selected from K 2 CO 3 ，K 3 PO 4 ，Na 2 CO 3 ，CsF，Cs 2 CO 3 Or t-Buona, the phosphine ligand being selected from the group consisting of P (t-Bu) 3 ，X-phos，PET 3 ，PMe 3 ，PPh 3 ，KPPh 2 Or P (t-Bu) 2 Cl。
8. Use of an organic light-emitting auxiliary material according to any one of claims 1 to 5 or prepared by a method according to any one of claims 6 to 7 for the preparation of an organic electroluminescent device.
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