CN108586188B - chrysene derivative, material containing chrysene derivative and organic electroluminescent device - Google Patents

chrysene derivative, material containing chrysene derivative and organic electroluminescent device Download PDF

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CN108586188B
CN108586188B CN201810556339.8A CN201810556339A CN108586188B CN 108586188 B CN108586188 B CN 108586188B CN 201810556339 A CN201810556339 A CN 201810556339A CN 108586188 B CN108586188 B CN 108586188B
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organic electroluminescent
derivative
compound
formula
organic
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CN108586188A (en
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曹建华
王士波
张建川
董梁
隋岩
唐永顺
华瑞茂
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Abstract

The invention discloses a
Figure DDA0001682561580000011
Derivatives, compositions containing the same
Figure DDA0001682561580000012
Derivative materials and organic electroluminescent devices. The above-mentioned
Figure DDA0001682561580000013
The structural formula of the derivative is shown as the following formula I:
Figure DDA0001682561580000014
the invention provides a compound of formula I
Figure DDA0001682561580000015
The derivative has a deep blue fluorescence property, overcomes the aggregated fluorescence quenching effect of fluorescent materials, and has a higher glass transition temperature, high thermal stability and excellent luminescence property. The synthesis process is simple, the purification method is simple and suitable for large-scale production, and the like, andthe luminescent property, the thermal stability and the like of the product can be adjusted by connecting different groups, so that the organic electroluminescent material is an ideal choice for being used as an organic luminescent layer material of an organic electroluminescent device. The OLED device using the fluorescent material has high fluorescence efficiency and good stability of the luminescent layer, so that the luminous efficiency and the service life of the device can meet the practical requirements.

Description

chrysene derivative, material containing chrysene derivative and organic electroluminescent device
Technical Field
The invention relates to the technical field of organic electroluminescence. More particularly, to
Figure BDA0001682561560000013
Derivatives, compositions containing the same
Figure BDA0001682561560000014
Derivative materials and organic electroluminescent devices.
Background
Organic electroluminescence (abbreviated as OLED) and related research firstly discovered the electroluminescence phenomenon of organic compound single crystal anthracene in pope et al as early as 1963. Kodak company of the United states of 1987 made an amorphous film device by evaporating small organic molecules, and reduced the driving voltage to within 20V. The device has the advantages of ultra-light weight, full curing, self luminescence, high brightness, wide viewing angle, high response speed, low driving voltage, low power consumption, bright color, high contrast, simple process, good temperature characteristic, soft display and the like, and can be widely applied to flat panel displays and surface light sources, so the device is widely researched, developed and used.
Through the development of twenty years, the organic light Emitting (EL) material has comprehensively realized red, blue and green light emission, and the application field has also been expanded from small molecules to the fields of high molecules, metal complexes and the like. In recent years, organic electroluminescent display technologies have become mature, and some products have entered the market, but in the course of industrialization, many problems still need to be solved, especially for various organic materials used for manufacturing devices, there are many problems that are still unsolved, such as carrier injection and transport performance, electroluminescent performance of materials, service life, color purity, matching between various materials and between various electrodes, and the like. Especially, the light emitting device has not yet achieved practical requirements in terms of luminous efficiency and service life, which greatly limits the development of OLED technology.
The metal complex phosphorescent material utilizing triplet state luminescence has high luminescence efficiency, and green and red materials of the metal complex have already met the use requirements, but the blue materials of the metal complex cannot meet the use requirements due to the special electronic structure characteristics of the metal complex. In one aspect, blue light is one of the three primary colors; on the other hand, a blue light material is often used as a matrix material, and green light or red light is obtained through an energy transfer mode. However, blue/deep blue OLEDs tend to have inferior performance to green or red OLEDs due to their wide bandgap. Currently, there are still few efficient deep blue materials that meet the blue standard (CIE coordinates (0.15,0.06)) of the European Broadcasting Union (EBU).
To date, many blue light emitting materials have been reported in the literature, and the structures of these materials can be roughly classified into anthracene derivatives, stilbene aromatic derivatives, pyrene derivatives, fluorene, and spirofluorene, among which anthracene derivatives are the progenitor materials applied to organic electroluminescent devices, such as 9, 10-Diphenylanthracene (DPA) and 9, 10-di (2-naphthyl) Anthracene (ADN), and although these materials have the advantages of high fluorescence quantum efficiency and good stability, their unstable thin films are one of the important reasons for accelerating device decay and causing device lifetime to be poor.
Therefore, the invention provides a high-efficiency heat-stability material
Figure BDA0001682561560000015
Derivatives, and compositions containing the same
Figure BDA0001682561560000016
Derivative materials and organic electroluminescent devices.
Disclosure of Invention
The first purpose of the invention is to provide
Figure BDA0001682561560000017
And (3) derivatives. According to the invention
Figure BDA0001682561560000018
Due to the non-planar structure of the derivative, different stable groups are introduced to form a larger conjugated system, so that molecular aggregation is effectively avoided, and the high-efficiency deep blue light material with good thermal stability is obtained.
A second object of the present invention is to provide a portable electronic device comprising the same
Figure BDA0001682561560000023
A derivative of the material.
It is a third object of the present invention to provide an organic electroluminescent device
In order to achieve the first purpose, the invention adopts the following technical scheme:
a kind of
Figure BDA0001682561560000024
The structural formula of the derivative is shown as the following formula I:
Figure BDA0001682561560000021
in the formula I:
R1、R2、R3、R4、R5、R6、R7and R8Each independently selected from hydrogen atom, deuterium hydrogen atom, C1-C20Alkyl radical, C2-C20Alkenyl radical, C2-C20Alkynyl, C1-C20Alkoxy radical, C3-C20Cycloalkyl radical, C3-C20Cycloalkene radicalSubstituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Oxygen-containing aryl, substituted or unsubstituted C2-C60Any one of heterocyclic aryl;
R9、R10and R11Each independently selected from a hydrogen atom, a deuterium hydrogen atom, a substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C2-C60Any one of heterocyclic aryl;
R12selected from substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Oxygen-containing aryl, substituted or unsubstituted C6-C60Sulfur-containing aryl, substituted or unsubstituted C6-C60Containing a phospharyl group, substituted or unsubstituted C6-C60Silicon-containing aryl, substituted or unsubstituted C6-C60Boron-containing aryl, substituted or unsubstituted C2-C60Any one of heterocyclic aryl groups.
Preferably, said C2-C60The heterocyclic aryl group is selected from any one of the groups shown as the following formulas II-1 to II-22:
Figure BDA0001682561560000022
Figure BDA0001682561560000031
in the formulas II-1 to II-20,
Figure BDA0001682561560000032
represents a substitution bit;
Z1、Z2and Z3Each independently selected from hydrogen, deuterium, hydrogen, halogen atom, hydroxyl group, nitrile group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl group or carboxylate thereof, sulfonic group or sulfonate thereof, phosphoric group or phosphate thereof、C1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, C1-C60Alkoxy radical, C3-C60Cycloalkyl radical, C3-C60Cycloalkenyl radical, C6-C60Aryl radicals containing at least one-F, -CN or C1-C10C of alkyl6-C60Aryl, substituted or unsubstituted C6-C60Oxygen-containing aryl, substituted or unsubstituted C6-C60Sulfur-containing aryl, substituted or unsubstituted C6-C60Boron-containing aryl, substituted or unsubstituted C6-C60Silicon-containing aryl, substituted or unsubstituted C6-C60Any one of phosphorus-containing aryl groups;
x1is an integer of 1 to 4;
x2is an integer of 1 to 3;
x3is an integer of 1 to 2;
x4is an integer of 1 to 6;
x5is an integer of 1 to 5;
T1is an oxygen or sulfur atom.
Preferably, said C6-C60The aryl group is selected from any one of phenyl, naphthyl, biphenyl, anthryl, bianthryl, pyrenyl, tetracenyl, phenanthryl, benzophenanthryl, benzanthryl, benzopyrenyl, fluorenyl and spirofluorenyl.
Preferably, said C6-C60The oxygen-containing aryl is selected from dibenzo [ b, d]Furan-2-yl, dibenzo [ b, d ]]Furan-4-yl, benzofuran-2-yl, benzofuran-5-yl, benzofuran-7-yl, 9-dimethylxanthen-4-yl, 9-dimethylxanthen-2-yl, spiro [ fluorene-9, 9' -xanthene]-2 '-yl, spiro [ fluorene-9, 9' -xanthene]Any of the-2-groups.
Preferably, said C6-C60The sulfur-containing aryl group is selected from dibenzo [ b, d ]]Thien-2-yl, dibenzo [ b, d ]]Thiophen-4-yl, 4-phenylsulfonylphenyl, benzothiophen-2-yl, benzothiophen-5-yl, benzothiophen-7-yl, 9,9-dimethylthioxanthen-4-yl, 9-dimethylthioxanthen-2-yl, spiro [ fluorene-9, 9' -thioxanthene]-2 '-yl, spiro [ fluorene-9, 9' -thiaanthracene]Any of the-2-groups.
Preferably, said C6-C60The phosphine-containing aryl group is selected from 4- (diphenylphosphinyl) phenyl, 3- (diphenylphosphinyl) phenyl, and dibenzo [ b ]]Phosphine oxide-5- (4-phenyl) -4-radical.
Preferably, said C6-C60The silicon-containing aryl is selected from any one of 4- (triphenylsilyl) phenyl, 4- (diphenylmethylsilyl) phenyl, 3- (triphenylsilyl) phenyl and 3- (diphenylmethylsilyl) phenyl.
Preferably, said C6-C60The boron-containing aryl group is selected from 4- (di (2,4, 6-trimethyl) phenyl) -borane phenyl, dibenzo [ b, d]Any one of borane-5-phenyl-4-yl and triphenylboron group.
Preferably, said substituted C6-C60Aryl, substituted C6-C60Oxygen-containing aryl, substituted C2-C60Heterocyclic aryl, substituted C6-C60Sulfur-containing aryl, substituted C6-C60Containing phospharyl radicals, substituted C6-C60Silicon-containing aryl, substituted C6-C60Containing boron aryl and substituted C2-C60The substituents in the heterocyclic aryl are each independently selected from hydrogen, deuterium, a halogen atom, C1-C20Alkyl radical, C2-C20Alkenyl radical, C2-C20Alkynyl, C1-C20Alkoxy radical, C3-C20Cycloalkyl and C3-C20One or more kinds of cyclic olefin groups.
Preferably, said substituted C6-C60Oxygen-containing aryl, substituted C6-C60Sulfur-containing aryl, substituted C6-C60Containing boron-aryl, substituted C6-C60Silicon-containing aryl and substituted C6-C60The substituent in the phosphorus-containing aryl is one or more selected from hydrogen, deuterium, halogen atom or aliphatic hydrocarbon group containing 1-8 carbon atoms.
Preferably, the structural formula is of formula I
Figure BDA0001682561560000042
The structural formula of the derivative is specifically shown as any one of the following formulas A-1 to A-149:
Figure BDA0001682561560000041
Figure BDA0001682561560000051
Figure BDA0001682561560000061
Figure BDA0001682561560000071
Figure BDA0001682561560000081
Figure BDA0001682561560000091
Figure BDA0001682561560000101
Figure BDA0001682561560000111
to achieve the second object, the present invention also provides a material whose raw material contains one or more of the above-mentioned materials
Figure BDA0001682561560000112
And (3) derivatives.
Preferably, the material is an organic electroluminescent material.
Preferably, the organic electroluminescent material is an organic light emitting diode material.
In addition, the above
Figure BDA0001682561560000113
The application of the derivative in preparing organic electroluminescent materials also belongs to the protection scope of the invention.
In order to achieve the third object, the present invention also provides an organic electroluminescent device, the material of which comprises the material
Figure BDA0001682561560000114
One or more of the derivatives.
Preferably, the organic electroluminescent device is an organic light emitting diode.
Preferably, the material of the organic light-emitting layer of the organic electroluminescent device comprises the above
Figure BDA0001682561560000115
One or more of the derivatives.
Preferably, the organic electroluminescent device may specifically have the following structure: the organic light-emitting diode comprises a transparent substrate, an anode layer, a hole transport layer, an organic light-emitting layer, an electron transport layer and a cathode layer from bottom to top in sequence.
Preferably, the organic electroluminescent device comprises a transparent substrate, an anode layer arranged on the transparent substrate, a hole transport layer arranged on the anode layer, an organic light emitting layer arranged on the hole transport layer, an electron transport layer arranged on the organic light emitting layer, and a cathode layer arranged on the electron transport layer.
Preferably, a hole injection layer is further arranged between the anode layer and the hole transport layer in the organic electroluminescent device.
Preferably, the material constituting the transparent substrate is glass or a flexible substrate.
Preferably, the material constituting the anode layer is an inorganic material or an organic conductive polymer; wherein the inorganic material is indium tin oxide, zinc oxide, tin zinc oxide, gold, silver or copper; the organic conductive polymer is selected from at least one of polythiophene, sodium polyvinyl benzene sulfonate and polyaniline.
Preferably, the material constituting the hole injection layer is TDATA, m-MTDATA or 2-TNATA; wherein the structural formulas of the TDATA, the m-MTDATA and the 2-TNATA are as follows:
Figure BDA0001682561560000121
preferably, the material constituting the hole transport layer is NPB or TPD; wherein the structural formula of the NPB is
Figure BDA0001682561560000122
The structural formula of the TPD is
Figure BDA0001682561560000123
Preferably, the material constituting the organic light-emitting layer is a compound represented by formula I, a mixture composed of a compound represented by formula I and a host material, or a mixture composed of a compound represented by formula I and a doping material; when the material forming the organic light-emitting layer is a mixture consisting of a compound shown in a formula I and a host material, the mass ratio of the compound shown in the formula I to the host material is 1-10: 90; when the material forming the organic light-emitting layer is a mixture of a compound shown in a formula I and a doping material, the mass ratio of the compound shown in the formula I to the doping material is 90: 1-10.
Preferably, the host material is selected from any one of PVK, DPEPO, DPTPO, TBADN, E3, ADN, α, β -ADN, NPA, PNA, or APBN:
Figure BDA0001682561560000131
preferably, the doping material is selected from any one of BD01, BD02, BD03, BD04, BD05, BD06, BD07, BD08, BD09, BD10, BD11, BD12, BD 13:
Figure BDA0001682561560000132
Figure BDA0001682561560000141
preferably, the material constituting the electron transport layer is selected from any one of compounds represented by Liq, Alq3, Gaq3, and BAlq:
Figure BDA0001682561560000142
preferably, the cathode layer is made of a material selected from any one or an alloy of any two of the following elements or fluorides of the following elements: lithium, magnesium, silver, calcium, strontium, aluminum, indium, copper, gold, and silver.
Preferably, the hole injection layer has a thickness of 30 to 50nm, and more preferably 40 nm.
Preferably, the hole transport layer has a thickness of 5 to 15nm, and more preferably 10 nm.
Preferably, the thickness of the organic light emitting layer is 10 to 100nm, and may be more preferably 40 nm.
Preferably, the thickness of the electron transport layer is 10 to 30nm, and more preferably 50 nm.
Preferably, the cathode layer has a thickness of 90-110nm, and more preferably 100 nm.
In addition, the above
Figure BDA0001682561560000143
The application of the derivative as an organic luminescent layer material in the preparation of organic electroluminescent devices also belongs to the protection scope of the invention.
The invention has the following beneficial effects:
the invention providesProvided by formula I
Figure BDA0001682561560000144
The derivative has a deep blue fluorescence property, overcomes the aggregated fluorescence quenching effect of fluorescent materials, and has a higher glass transition temperature, high thermal stability and excellent luminescence property. The synthesis process is simple, the purification method is simple and suitable for large-scale production, and the like, and the luminescent property, the thermal stability and the like of the product can be adjusted by connecting different groups, so that the method is an ideal choice for being used as an organic luminescent layer material of an organic electroluminescent device. The OLED device using the fluorescent material has high fluorescence efficiency and good stability of the luminescent layer, so that the luminous efficiency and the service life of the device can meet the practical requirements.
Drawings
The following describes embodiments of the present invention in further detail with reference to the accompanying drawings.
FIG. 1 shows a block diagram of the application of the compound of formula I according to the invention in an OLED device; wherein, the organic electroluminescent device comprises a 1-transparent substrate, a 2-anode layer, a 3-hole injection layer, a 4-hole transport layer, a 5-organic luminescent layer, a 6-electron transport layer and a 7-cathode layer.
FIG. 2 shows a scheme for the synthesis of compounds of formula I according to the invention.
Detailed Description
In order to more clearly illustrate the invention, the invention is further described below with reference to preferred embodiments and the accompanying drawings. Similar parts in the figures are denoted by the same reference numerals. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
In the present invention, the preparation methods are all conventional methods unless otherwise specified. The starting materials used are commercially available from published sources unless otherwise specified.
The compound shown in the formula I provided by the invention can be prepared according to the method shown in figure 2. In FIG. 2, the intermediate compound int.1 has the structural formula, R1、R2、R3、R4、R5、R6、R7、R8、R9、R10And R11Is as defined in formula I, and Ar is as defined in formula I for R12The same definition is applied.
The following examples are provided for testing the performance of OLED materials and devices using the following test apparatus and method:
OLED device performance detection conditions:
luminance and chromaticity coordinates: testing with a photosresearch PR-715 spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: tested using NEWPORT 1931-C.
Example 1 preparation of Compound of formula A-1
First step, 11- (4-bromophenyl) -3-chloro
Figure BDA0001682561560000152
The preparation route is as follows:
Figure BDA0001682561560000151
the specific operation flow of the preparation is as follows:
20.0g (0.07mol) of the starting SM-0 was dissolved in 360ml of anhydrous dichloromethane, cooled to 0 ℃ in an ice salt bath, and 13.5g (46.8mmol) of the starting SM-1 was added thereto, and a solution of 11.2g (74.9mmol) of trifluoromethanesulfonic acid in dichloromethane was slowly added dropwise, and the mixture was stirred for reaction for 1 hour, heated to 30 ℃ and stirred for reaction for 18 hours, and then concentrated to dryness under reduced pressure, separated and purified by a silica gel column, and concentrated to dryness under reduced pressure to obtain 13.2g of a white solid with a yield of 45%.
The second step, the preparation of 2-bromo-4, 4' -dibromomethylenebiphenyl, the preparation route is as follows:
Figure BDA0001682561560000161
the specific operation flow of the preparation is as follows:
5.0g (11.97mmol) of the intermediate int. -1 from the previous step was dissolved in 100ml of tetrahydrofuran, 5.2g (30mmol) of 1-naphthylboronic acid was added, 8.3g (60mmol) of anhydrous potassium carbonate and 10ml of water were added, 0.2g (0.89mmol) of palladium acetate and 466.8mg (1.78mmol) of triphenylphosphine were further added, the mixture was stirred under reflux at elevated temperature for 16 hours, cooled to room temperature, concentrated to dryness under reduced pressure, extracted with dichloromethane and water, the organic phase was collected, dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated to dryness under reduced pressure, separated and purified by a silica gel column, concentrated to dryness under reduced pressure to give 5.8g of a white solid with a yield of 87%.
Experimental data:
(1)1HNMR(δ、CDCl3)：9.17(s,1H),8.89(d,1H),8.56(d,2H),8.34(m,3H),7.99(d,2H),7.93(t,1H),7.89(m,2H),7.77～7.48(m,10H),7.39～7.36(m,2H),7.18(s,4H)；
(2)HRMS：C44H28standard molecular weight 556.2191, test result 556.2183[ M +]；
Example 2 preparation of Compound of formula A-17
First, intermediate 2, 9-dichloro-5- (1-naphthyl)
Figure BDA0001682561560000163
The preparation route is as follows:
Figure BDA0001682561560000162
the specific operation flow of the preparation is as follows:
referring to the first step of the procedure of example 1, SM-1 of the first step of example 1 was replaced with SM-4 to give the intermediate int.
The second step, the preparation of the compound of formula A-17, is as follows:
Figure BDA0001682561560000171
the specific operation flow of the preparation is as follows:
10g (23.6mmol) of the intermediate int. -2, 6.9g (56.5 mmol) of the previous step) 1.36g (1.2mmol) of Pd (PPh) as a palladium catalyst3)4And 10g (94.3mmol) of sodium carbonate, then 60ml of toluene, 20ml of ethanol and 20ml of water are added, the mixture is heated and refluxed and stirred for reaction for 12 hours under the protection of nitrogen, the mixture is cooled to room temperature and is extracted by ethyl acetate, an organic phase is dried by anhydrous sodium sulfate, the filtration is carried out, the filtrate is decompressed, concentrated and dried, and is separated and purified by a silica gel column, petroleum ether-ethyl acetate is eluted, and then tetrahydrofuran is used for recrystallization, 7.0g of white solid is obtained, and the yield is 58%.
Experimental data:
(1)1HNMR(δ、CDCl3)：9.16(s,1H),9.04(d,1H),8.86(m,1H),8.49～8.34(m,5H),8.18(s,1H),8.15～7.91(m,3H),7.87～7.72(m,6H),7.69～7.36(m,8H)；
(2)HRMS：C40H26standard molecular weight 506.2035, test result 506.2026[ M +]；
Example 3 preparation of Compound of formula A-33
First step, intermediate 11- ([1,1' -biphenyl)]-2-yl) -2-chloro
Figure BDA0001682561560000173
The preparation route is as follows:
Figure BDA0001682561560000172
the specific operation flow of the preparation is as follows:
referring to the first step of the preparation of example 1, SM-0 was replaced with SM-5 and SM-1 was replaced with SM-6 in the first step of example 1 to give intermediate int. -3 as a white solid with a yield of 47%.
The second step, the preparation of the compound of formula A-33, is as follows:
Figure BDA0001682561560000181
the specific operation flow of the preparation is as follows:
referring to the second step of the preparation of example 2, int. -2 of the second step of example 2 was replaced with int. -3 and phenylboronic acid was replaced with 2-phenylboronic acid to give product a-33 as a white solid with a yield of 88%.
Experimental data:
(1)1HNMR(δ、CDCl3)：9.06(d,1H),8.86(m,1H),8.42～8.38(t,2H),8.34(s,1H),7.87～7.78(m,6H),7.70～7.58(m,11H),7.37～7.34(m,6H)；
(2)HRMS：C42H28standard molecular weight 532.2191, test result 532.2178[ M +]。
The following compounds were prepared by reference to the synthesis procedures of example 1, example 2 or example 3, i.e. the procedure was the same as example 1 or example 2 or example 3, except that different reactants were used instead of SM-1 in the first step of example 1 and SM-2 in the second step of example 1, as required, depending on the desired product; or in place of SM-4 of the first step of example 2 in place of phenylboronic acid of the second step of example 2; or 2-phenylphenylboronic acid in the second step of example 3, instead of SM-6 in the first step of example 3, and the amount of this compound to be used by mass was changed in accordance with the molar amount, as shown in Table 1:
table 1 results of mass spectrometric testing of different compounds
Figure BDA0001682561560000182
Figure BDA0001682561560000191
Figure BDA0001682561560000201
Figure BDA0001682561560000211
Figure BDA0001682561560000221
Example 4 preparation of Compound of formula A-4
The preparation route is as follows:
Figure BDA0001682561560000222
the specific operation flow of the preparation is as follows:
5.0g (11.97mmol) of the intermediate int. -1 prepared in the first step of example 1 are dissolved in 80ml of xylene, 5.9g (30.0mmol) of 4, 4' -dimethyl-diphenylamine and 3.0g (32mmol) of sodium tert-butoxide are added, and 124mg (0.12mmol) of the palladium catalyst Pd are added under nitrogen protection2(dba)3CHCl3And 0.2ml of 90% toluene solution of tri-tert-butylphosphine, heating to 120 ℃, stirring for reaction for 16 hours, cooling to room temperature, adding 50ml of water, stirring for 30 minutes, filtering, washing a filter cake with ethanol, drying, and recrystallizing with toluene-tetrahydrofuran to obtain 6.8g of yellow solid with the yield of 82%.
Experimental data:
(1)1HNMR(δ、CDCl3)：8.78(d,1H)，8.64(s,1H)，8.08(s,1H)，7.45～7.41(m,3H)，7.39～7.28(m,8H)，7.22～7.07(m,16H)，2.42(s,12H)；
(2)HRMS：C52H42N2standard molecular weight 694.3348, test result 695.3326[ M + H ]]。
Referring to the synthesis procedure of example 4, a compound of formula a-5 was prepared, i.e. the procedure was the same as in example 4, except that different reactants were used instead of SM-3 of example 4 according to actual needs, depending on the desired product, and the mass usage of the compound was changed according to molar weight, the experimental data HRMS of compound a-5: c60H38N2O2Standard molecular weight 818.2933, test result 819.2778[ M + H ]]。
Example 5 preparation of Compound of formula A-148
First step, intermediate 2- (8, 9-dichloro)
Figure BDA0001682561560000234
Preparation of (E) -5-yl) -4, 6-diphenyl-1, 3, 5-triazine by the following route:
Figure BDA0001682561560000231
the specific operation flow of the preparation is as follows:
referring to the first step of the preparation of example 1, SM-0 was replaced with SM-7 and SM-1 was replaced with SM-8 in the first step of example 1 to give intermediate int.
In the second step, an intermediate int. -5 is prepared by the following preparation route:
Figure BDA0001682561560000232
the specific operation flow of the preparation is as follows:
referring to the second step preparation of example 2, the second step int. -2 of example 2 was replaced with int. -4 to give intermediate int. -5 as a yellow solid in 76% yield.
The third step, the preparation of the compound of formula A-148, the preparation route is as follows:
Figure BDA0001682561560000233
the specific operation flow of the preparation is as follows:
5g (8.1mmol) of the intermediate int. -5 in the previous step, 13.5g (81.7mmol) of anhydrous ferric chloride and 250ml of dichloromethane are heated under reflux and stirred for reaction for 12 hours under the protection of nitrogen, the reaction solution is cooled to room temperature, the filtrate is filtered, concentrated under reduced pressure and dried, separated and purified by a silica gel column, and eluted by petroleum ether-ethyl acetate to obtain 4.5g of white solid with the yield of 90%.
Experimental data:
(1)1HNMR(δ、CDCl3)：9.47(d,2H),9.02(s,1H),8.58(d,1H),8.49(s,1H),8.35～8.28(m,5H),7.82～7.68(m,9H),7.64～7.49(m,8H)；
(2)HRMS：C45H27N3standard molecular weight 609.2205, test result 610.2184[ M + H ]]。
Referring to the synthesis procedure of example 5, compounds of formulae a-146 and a-147, respectively, were prepared, i.e. the procedure was the same as example 5 except that different reactants were used as required to replace SM-8 in the first step of example 5 and the mass amounts of the compounds were varied according to molar amounts, according to the desired product, compound a-146 experimental data HRMS: c38H26Standard molecular weight 482.2035, test result 483.1910[ M + H ]](ii) a Experimental data HRMS for Compound A-147: c40H24Standard molecular weight 504.1878, test result 505.1722[ M + H ]]。
Example 6 preparation of devices OLED-1 to OLED-4
An organic electroluminescent device, the structure of which is shown in fig. 1, comprises a transparent substrate 1, an anode layer 2 arranged on the transparent substrate 1, a hole injection layer 3 arranged on the anode layer 2, a hole transport layer 4 arranged on the hole injection layer 3, an organic light emitting layer 5 arranged on the hole transport layer 4, an electron transport layer 6 arranged on the organic light emitting layer 5, and a cathode layer 7 arranged on the electron transport layer 6, and the preparation comprises the following steps:
1) the glass substrate coated with the ITO conductive layer is subjected to ultrasonic treatment in a cleaning agent for 30 minutes, washed in deionized water, subjected to ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baked to be completely dry in a clean environment, irradiated by an ultraviolet light cleaning machine for 10 minutes, and bombarded on the surface by a low-energy cation beam.
2) Placing the processed ITO glass substrate in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-4Pa, evaporating a compound 2-TNATA serving as a hole injection layer on the anode layer film at the evaporation rate of 0.1nm/s and at the evaporation film thickness of 40 nm;
3) continuously evaporating NPB on the hole injection layer to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
4) the compound a-1 obtained in example 1 of the present invention was further deposited as a host material, BD05 was used as a dopant material, and the ratio of the compound a-1: the mass ratio of BD05 was 90:10, the evaporation rate of the organic light-emitting layer as a device was 0.1nm/s, and the thickness of the organic light-emitting layer obtained by evaporation was 40 nm;
5) continuously evaporating a Liq layer on the organic light-emitting layer to serve as an electron transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 50 nm;
6) and sequentially evaporating a magnesium/silver alloy layer on the electron transport layer to serve as a cathode layer of the device, wherein the evaporation rate of the magnesium/silver alloy layer is 2.0-3.0 nm/s, the evaporation film thickness is 100nm, and the mass ratio of magnesium to silver is 1: and 9, obtaining the OLED device OLED-1 provided by the invention.
The compound a-1 in step 4) was replaced with the compound a-17 prepared in example 3 according to the same procedure as above to obtain an OLED-2 provided by the present invention;
the compound A-1 in step 4) was replaced with the compound A-33 prepared in example 4 according to the same procedure as above to obtain OLED-3 provided by the present invention;
replacing the compound A-1 in the step 4) with a compound alpha, beta-ADN according to the same steps to obtain the OLED-4 serving as a comparison device;
the results of the performance tests of the obtained devices OLED-1 to OLED-4 are shown in Table 2.
TABLE 2 Performance test results of OLED-1 to OLED-4
Figure BDA0001682561560000251
As can be seen from the above, the device prepared from the organic material of the invention has low lighting voltage and the brightness current density of 10mA/cm2Under the condition, the brightness of the device exceeds 820Cd/m of a reference device OLED-42And the T97 lifetime of the device exceeded that of the reference device.
Example 7 preparation of devices OLED-5 to OLED-8
An organic electroluminescent device having the same structure as in example 6 was prepared by the following steps:
1) the glass substrate coated with the ITO conductive layer is subjected to ultrasonic treatment in a cleaning agent for 30 minutes, washed in deionized water, subjected to ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baked to be completely dry in a clean environment, irradiated by an ultraviolet light cleaning machine for 10 minutes, and bombarded on the surface by a low-energy cation beam.
2) Placing the processed ITO glass substrate in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-4Pa, evaporating a compound 2-TNATA serving as a hole injection layer on the anode layer film at the evaporation rate of 0.1nm/s and at the evaporation film thickness of 40 nm;
3) continuously evaporating NPB on the hole injection layer to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
4) the compound a-4 obtained in example 2 of the present invention was further deposited on the hole transport layer as a dopant, α, β -ADN was used as a host, α, β -ADN: the mass ratio of the compound A-4 is 90:10, the compound A-4 is used as an organic light-emitting layer of a device, the evaporation rate is 0.1nm/s, and the thickness of the organic light-emitting layer obtained by evaporation is 40 nm;
5) continuously evaporating a Liq layer on the organic light-emitting layer to serve as an electron transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 50 nm;
6) and sequentially evaporating a magnesium/silver alloy layer on the electron transport layer to serve as a cathode layer of the device, wherein the evaporation rate of the magnesium/silver alloy layer is 2.0-3.0 nm/s, the evaporation film thickness is 100nm, and the mass ratio of magnesium to silver is 1: and 9, obtaining the OLED device OLED-5 provided by the invention.
Replacing the compound A-4 in the step 4) with a compound A-2 according to the same steps as the above to obtain the OLED-6 provided by the invention;
replacing the compound A-4 in the step 4) with a compound A-107 according to the same steps as above to obtain the OLED-7 provided by the invention;
replacing the compound A-4 in the step 4) with the compound BD01 according to the same steps as above to obtain the OLED-8 provided by the invention as a comparison device;
the results of the performance tests of the obtained devices OLED-5 to OLED-8 are shown in Table 3.
TABLE 3 Performance test results for OLED-5 to OLED-8
Figure BDA0001682561560000261
As can be seen from the above, the device prepared from the organic material of the invention has low lighting voltage and the brightness current density of 10mA/cm2Under the condition, the brightness of the device exceeds 900Cd/m of a reference device OLED-82And the T97 lifetime of the device exceeded that of the reference device.
It should be understood that the above-mentioned embodiments of the present invention are only examples for clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention, and it will be obvious to those skilled in the art that other variations or modifications may be made on the basis of the above description, and all embodiments may not be exhaustive, and all obvious variations or modifications may be included within the scope of the present invention.

Claims (6)

1. A kind of
Figure FDA0003025894370000011
Derivatives characterized in that
Figure FDA0003025894370000012
The structural formula of the derivative is specifically shown as any one of the following formulas:
Figure FDA0003025894370000013
2. a material comprising the material of claim 1
Figure FDA0003025894370000014
And (3) derivatives.
3. The method of claim 1
Figure FDA0003025894370000015
The application of the derivative in preparing organic electroluminescent materials.
4. An organic electroluminescent device comprising the compound according to claim 1
Figure FDA0003025894370000016
And (3) derivatives.
5. The organic electroluminescent device according to claim 4, wherein the organic electroluminescent element is a thin film transistor
Figure FDA0003025894370000017
The derivative is a material constituting an organic light emitting layer of the electroluminescent device.
6. The method of claim 1
Figure FDA0003025894370000018
Use of the derivatives in the preparation of organic electroluminescent devices.
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