CN111039962A - Nitrogen-containing compound, application thereof and organic electroluminescent device using nitrogen-containing compound - Google Patents

Nitrogen-containing compound, application thereof and organic electroluminescent device using nitrogen-containing compound Download PDF

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CN111039962A
CN111039962A CN201911402910.1A CN201911402910A CN111039962A CN 111039962 A CN111039962 A CN 111039962A CN 201911402910 A CN201911402910 A CN 201911402910A CN 111039962 A CN111039962 A CN 111039962A
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CN111039962B (en
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王金平
薛震
陈志伟
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Abstract

The invention relates to a nitrogen-containing compound, which has a structure shown in a formula (1) or a formula (2), wherein Ar is selected from substituted or unsubstituted aryl with 6-60 carbon atoms or substituted or unsubstituted heteroaryl with 2-60 carbon atoms; l is selected from arylene with 12-40 carbon atoms. The nitrogen-containing compound is used for an electron transport layer in an organic electroluminescent device, can reduce the driving voltage of the organic electroluminescent device, and improves the luminous efficiency and the service life.
Figure DDA0002347907240000011

Description

Nitrogen-containing compound, application thereof and organic electroluminescent device using nitrogen-containing compound
Technical Field
The invention belongs to the technical field of organic light-emitting materials, and particularly provides a nitrogen-containing compound, application thereof and an organic electroluminescent device using the nitrogen-containing compound.
Background
An organic light-emitting diode (OLED) is an OLED, and its light-emitting principle is that when an electric field is applied to a cathode and an anode, a hole on the anode side and an electron on the cathode side move to a light-emitting layer, and combine to form an exciton in the light-emitting layer, the exciton is in an excited state and releases energy to the outside, and the process of releasing energy from the excited state to a ground state releases energy emits light to the outside. Since Kodak corporation reports electroluminescence of organic molecules in 1987 and Cambridge university in England reports electroluminescence of polymers in 1990, various countries in the world have developed research and development. The material has the advantages of simple structure, high yield, low cost, active luminescence, high response speed, high fraction and the like. And has the properties of low driving voltage, all solid state, non-vacuum, oscillation resistance, low temperature resistance (-40 ℃) and the like, is considered to be a new technology which is most likely to replace the liquid crystal display in the future, and draws great attention.
The organic charge transport material is an organic semiconductor material which can realize the controllable directional ordered migration of carriers under the action of an electric field when the carriers (electrons or holes) are injected, thereby realizing charge transport. Compared with inorganic materials, the organic charge transport material has the advantages of low cost, low toxicity, easy processing and forming, chemical modification to meet different requirements, capability of manufacturing fully flexible devices and the like. The organic charge transport material may be divided into an organic hole transport (p-type) material and an organic electron transport (n-type) material. N-type materials have evolved more slowly than organic p-type materials, such as 8-hydroxyquinoline aluminum (Aq3) and oxadiazole derivative PBD, which were studied earlier.
The organic electron transport material for application should have high thermal stability, high glass transition temperature, high electron mobility, and low LUMO level (favorable for electron injection). Although a large number of organic electron transport materials have been reported, it has been challenging to design and synthesize organic small molecule electron transport materials with excellent overall properties.
Disclosure of Invention
In order to improve the luminous efficiency and the device life of an organic electroluminescent device, the invention aims to provide a nitrogen-containing compound, application thereof and an organic electroluminescent device using the nitrogen-containing compound.
In order to achieve the above object, a first aspect of the present invention provides a nitrogen-containing compound having a structure represented by the following formula (1) or formula (2):
Figure BDA0002347907220000021
wherein Ar is selected from substituted or unsubstituted aryl with 6-60 carbon atoms, or substituted or unsubstituted heteroaryl with 2-60 carbon atoms; l is selected from arylene with 12-40 carbon atoms;
the substituent of Ar is selected from deuterium, halogen, cyano, alkyl with 1-6 carbon atoms or a group shown as a formula (1-1):
Figure BDA0002347907220000022
in a second aspect, the present invention provides a use of the nitrogen-containing compound provided in the first aspect of the present invention in an organic electroluminescent device.
In a third aspect, the present invention provides an organic electroluminescent device, comprising an anode, a cathode, and at least one functional layer interposed between the anode and the cathode, wherein the functional layer comprises a hole injection layer, a hole transport layer, an organic electroluminescent layer, an electron transport layer, and an electron injection layer, and the electron transport layer contains the nitrogen-containing compound provided in the first aspect of the present invention.
Through the technical scheme, the nitrogen-containing compound is used for an electron transport layer in an organic electroluminescent device, so that the luminous efficiency and the service life of the organic electroluminescent device can be effectively improved, and the device can meet the requirement of lower driving voltage.
Additional features and advantages of the invention will be set forth in the detailed description which follows.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the principles of the invention and not to limit the invention. In the drawings:
fig. 1 is a schematic structural view of an embodiment of the organic electroluminescent device of the present invention.
Description of the reference numerals
100: anode 200: cathode 300: functional layer
310: hole injection layer 320: hole transport layer 321: a first hole transport layer
322: second hole transport layer 330: organic electroluminescent layer 340: hole blocking layer
350: electron transport layer 360: electron injection layer 370: electron blocking layer
Detailed Description
The following detailed description of embodiments of the invention refers to the accompanying drawings. It should be understood that the detailed description and specific examples, while indicating the present invention, are given by way of illustration and explanation only, not limitation.
The terms "the" and "said" are used to indicate the presence of one or more elements/components/etc.; the terms "comprising" and "having" are intended to be inclusive and mean that there may be additional elements/components/etc. other than the listed elements/components/etc.
The first aspect of the present invention provides a nitrogen-containing compound having a structure represented by the following formula (1) or formula (2):
Figure BDA0002347907220000041
wherein Ar is selected from substituted or unsubstituted aryl with 6-60 carbon atoms, or substituted or unsubstituted heteroaryl with 2-60 carbon atoms; l is selected from arylene with 12-40 carbon atoms;
the substituent of Ar is selected from deuterium, halogen, cyano, alkyl with 1-6 carbon atoms or a group shown as a formula (1-1):
Figure BDA0002347907220000042
the nitrogen-containing compound of the invention is a derivative taking oxazine acridine as a mother nucleus. The acridine group has a stable structure, high glass transition temperature, high electron mobility and low energy level. The acridine group is combined with the oxazine group, a conjugated system is increased, and the continuous pi conjugate ties better electron mobility, so that the high electron mobility is realized; and, the combination of both makes carrier transport balanced. The nitrogen-containing compound can be used as an electron transport layer material of an organic electroluminescent device, and the organic electroluminescent device prepared by the nitrogen-containing compound has lower driving voltage, higher luminous efficiency and longer service life.
In the present invention, the term "substituted or unsubstituted" means that a functional group described later in the term may or may not have a substituent Ra. For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Ra or an unsubstituted aryl group. Ra is deuterium, halogen, cyano, alkyl having 1 to 6 carbon atoms, or diphenylphosphinyl group represented by formula (1-1). The aryl group may include 1 or two or more of the substituents Ra.
In one embodiment of the present invention, the substituents Ra of Ar may each independently be selected from one or more of methyl, cyano, diphenylphosphinyl, ethyl, n-propyl, isopropyl, n-butyl and tert-butyl.
In the present invention, an "aryl group" is a residual atomic group obtained by removing 1 hydrogen atom bonded to a carbon atom constituting an aromatic ring from an aromatic hydrocarbon. The aryl group may be a monocyclic aryl group or a polycyclic aryl group, including aryl groups having a benzene ring, aryl groups having a condensed ring, in other words, the aryl group may be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected through a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected through a carbon-carbon bond conjugate, two or more condensed ring aryl groups connected through a carbon-carbon bond conjugate. In addition, monocyclic aryl groups linked by alkylene (e.g., methylene), cycloalkylene (e.g., cycloalkylene) groups are also considered aryl groups herein. Specific examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, anthracenyl, phenanthrenyl, biphenylyl, terphenyl, quaterphenyl, pentabiphenyl, hexabiphenyl, benzo [9,10] phenanthryl, pyrenyl, benzofluoranthenyl, chrysene yl, and the like. It is understood that the number of carbon atoms of the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group; for example, a substituted aryl group having 6 to 60 carbon atoms refers to an aryl group and the total number of carbon atoms in the substituents on the aryl group is 6 to 60.
In the present invention, arylene means a group formed by loss of one H from an aryl group.
In the present invention, the heteroaryl group may be a heteroaryl group including at least one of B, O, N, Si and S as a heteroatom. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Specific examples of heteroaryl groups include, but are not limited to, thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzosilyl, dibenzofuryl, phenyl-substituted dibenzofuryl, Dibenzofuranyl-substituted phenyl groups, and the like. Wherein, thienyl, furyl, phenanthroline and the like are heteroaryl of a single aromatic ring system, and N-aryl carbazolyl, N-heteroaryl carbazolyl, phenyl-substituted dibenzofuryl and the like are heteroaryl of a plurality of aromatic ring systems connected by carbon-carbon bond conjugation. It is understood that the number of carbon atoms of the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituent on the heteroaryl group; for example, a substituted heteroaryl group having 2 to 60 carbon atoms refers to a heteroaryl group and a substituent group on the heteroaryl group having 2 to 60 total carbon atoms. According to a specific embodiment, the heteroatom of the heteroaryl group comprises N.
In the present invention, when Ar has a substituent, the substituent of Ar is selected from deuterium, halogen, cyano, alkyl having 1 to 6 carbon atoms, or a group represented by the formula (1-1):
Figure BDA0002347907220000061
in the invention, the alkyl with 1-6 carbon atoms comprises straight-chain alkyl with 1-6 carbon atoms and branched-chain alkyl with 3-6 carbon atoms; the number of carbon atoms of the alkyl group is, for example, 1, 2, 3, 4, 5, 6, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, n-hexyl, and the like.
According to a specific embodiment, Ar has one or more substituents, and each substituent is independently one or more selected from cyano groups or alkyl groups having 1 to 4 carbon atoms. The alkyl group having 1 to 4 carbon atoms may be, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, or the like.
Alternatively, Ar is selected from substituted or unsubstituted aryl groups having 6 to 45 carbon atoms, or substituted or unsubstituted heteroaryl groups having 8 to 45 carbon atoms.
Alternatively, Ar is selected from substituted or unsubstituted aryl groups having 18 to 42 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12 to 42 carbon atoms.
According to a particular embodiment, Ar is selected from the group consisting of:
Figure BDA0002347907220000062
Figure BDA0002347907220000071
Figure BDA0002347907220000072
alternatively, in this embodiment, Ar may also be optionally substituted with the substituents described above.
According to a preferred embodiment, Ar is selected from the group consisting of:
Figure BDA0002347907220000073
Figure BDA0002347907220000081
according to one embodiment, L may be selected from arylene groups having 12 to 25 carbon atoms.
Alternatively, L is selected from the group consisting of:
Figure BDA0002347907220000082
in one embodiment of the present invention, the nitrogen-containing compound may be selected from one or more of the following compounds P1-P80:
Figure BDA0002347907220000083
Figure BDA0002347907220000091
Figure BDA0002347907220000101
Figure BDA0002347907220000111
Figure BDA0002347907220000121
the method for synthesizing the nitrogen-containing compound provided by the present invention is not particularly limited, and those skilled in the art can determine an appropriate synthesis method based on the nitrogen-containing compound of the present invention in combination with the preparation methods of the examples. In other words, the examples section of the present invention illustratively provides methods for the preparation of nitrogen-containing compounds, using starting materials that are commercially available or are well known in the art. All of the nitrogen-containing compounds provided by the present invention can be obtained by the methods of preparation according to these illustrative examples by those skilled in the art, and all of the specific methods of preparation for the nitrogen-containing compounds will not be described in detail herein, and those skilled in the art should not be construed as limiting the invention.
In a second aspect, the present invention provides a use of the nitrogen-containing compound provided in the first aspect of the present invention in an organic electroluminescent device.
According to the present invention, the nitrogen-containing compound can be used as an electron transport layer material for an organic electroluminescent device. The nitrogen-containing compound is a derivative taking oxazine acridine as a mother nucleus, has high glass transition temperature and high thermal decomposition temperature, and can be applied to organic electroluminescent devices with high efficiency and long service life by taking the nitrogen-containing compound as an organic small molecule electron transport layer material.
In a third aspect, the present invention provides an organic electroluminescent device, comprising an anode, a cathode, and at least one functional layer interposed between the anode and the cathode, wherein the functional layer comprises a hole injection layer, a hole transport layer, an organic electroluminescent layer, an electron transport layer, and an electron injection layer, and the electron transport layer contains the nitrogen-containing compound provided in the first aspect of the present invention. Optionally, the electron transport layer contains at least one of the compounds P1-P80.
According to one embodiment, as shown in fig. 1, the organic electroluminescent device includes an anode 100 and a cathode 200 oppositely disposed, and a functional layer 300 (i.e., an organic layer) disposed between the anode 100 and the cathode 200.
Specifically, the organic electroluminescent device includes an anode 100, a hole injection layer 310, a hole transport layer 320, an organic electroluminescent layer 330 (i.e., a light emitting layer), an electron transport layer 350, an electron injection layer 360, and a cathode 200, which are sequentially stacked. The hole transport layer 320 may include one layer or two layers.
Optionally, a hole blocking layer 340 is further disposed between the organic electroluminescent layer 330 and the electron transport layer 350.
Optionally, an electron blocking layer 370 may be further disposed between the organic electroluminescent layer 330 and the hole transport layer 320.
According to an exemplary embodiment, the hole transport layer 320 may be composed of a first hole transport layer 321 and a second hole transport layer 322, the first hole transport layer 321 being relatively close to the anode.
Based on the excellent performance of the compound, the organic electroluminescent device can reduce the driving voltage of the organic electroluminescent device, improve the luminous efficiency and prolong the service life of the device by using the compound as an electron transport layer material.
The invention is further illustrated by the following examples, but is not to be construed as being limited thereto.
Compounds of synthetic methods not mentioned in the present invention are all commercially available starting products.
The method for synthesizing the nitrogen-containing compound of the present invention will be specifically described below with reference to synthesis examples 1 to 23.
To facilitate understanding of the invention, the following starting materials correspond to the numbers of the compounds prepared, for example starting material Ia for compound PI, for example starting material 1a for compound P1 and starting material 7a for compound P7.
Synthesis example 1
20g of polyphosphoric acid (CAS No: 8017-16-1) is added into a reaction bottle, heating is started, when the temperature is raised to 90 ℃, 3.38g of raw material 1a (10.5mmol, CAS No: 2272-04-0) and 2.10g of raw material A (CAS:23045-30-9, 10mmol) are sequentially added into the reaction bottle, the temperature is raised to 145 ℃ continuously, and the reaction is kept at the temperature. Stopping the reaction when the reaction of the raw materials is completed by liquid phase monitoring, cooling the reaction solution to below 50 ℃, slowly adding water into the reaction solution, starting stirring, filtering, adjusting the filtrate to be alkalescent (pH is 9-10) by using a sodium hydroxide aqueous solution (mass fraction is 40%), extracting for 2 times by using ethyl acetate, separating the liquid, and combining organic phases. Washing the organic phase to neutralityThe residue was dried over anhydrous sodium sulfate l h, filtered to remove the drying agent to give a cake, the cake was rinsed with a small amount of ethyl acetate, the filtrates were combined, and the filtrate was concentrated and purified by column chromatography to give Compound P1(3.23g, yield 67%). 497.1[ M + H ] M/z]+。
The calculated value of the element content of the compound P1 is C32H21N2O2P: wherein C: 77.41, respectively; h: 4.26; n: 5.64 of; o: 6.44; p: 6.24. measured value C32H21N2O2P: wherein C: 77.34; h: 4.22; n: 5.81; o: 6.23; p: 6.57.
Figure BDA0002347907220000141
synthesis example 2
20g of polyphosphoric acid is added into a reaction bottle, heating is started, when the temperature is raised to 100 ℃, 2.74g of raw material 2a (11mmol, CAS No: 216059-95-9) and 2.1g of raw material A (10mmol) are sequentially added into the reaction bottle, the temperature is continuously raised to 150 ℃, and the reaction is carried out under the condition of heat preservation. Stopping the reaction when the reaction of the raw materials is completed by liquid phase monitoring, cooling the reaction solution to below 50 ℃, slowly adding water into the reaction solution, starting stirring, filtering, adjusting the pH value to be alkalescent (9-10) by using a sodium hydroxide aqueous solution (the mass fraction is 40%), extracting for 2 times by using ethyl acetate, separating the liquid, and combining organic phases. Washing the organic phase to be neutral, drying l h with anhydrous sodium sulfate, filtering to remove the drying agent to obtain a filter cake, leaching the filter cake with ethyl acetate, combining the filtrates, concentrating the filtrate, and purifying by a column to obtain the compound P2. (4.23g, yield 75%). 424.1[ M + H ] M/z]+。
Calculated value C of element content (%) of Compound P229H17N3O: wherein C: 82.25 of; h: 4.05; n: 9.92; o: 3.78; measured value C29H17N3O: wherein C: 82.16, respectively; h: 4.08 of; n: 9.97 of; o: 3.79.
Figure BDA0002347907220000151
synthesis example 3
20g of polyphosphoric acid is added into a reaction bottle, heating is started, when the temperature is raised to 100 ℃, 2.98g of raw material 7a (10mmol, CAS No: 63018-91-7) and 2.1g of raw material A (10mmol) are sequentially added into the reaction bottle, the temperature is continuously raised to 150 ℃, and the reaction is kept at the temperature. Stopping the reaction when the raw materials completely react, cooling the reaction solution to below 50 ℃, slowly adding water into the reaction solution, starting stirring, filtering, adjusting the filtrate to alkalescence (pH is 9-10) by using an aqueous solution of sodium hydroxide (mass fraction is 40%), extracting for 2 times by using ethyl acetate, separating the liquid, and combining organic phases. The organic phase was washed with water to neutrality, dried l h over anhydrous sodium sulfate, filtered to remove the drying agent to give a filter cake, which was rinsed with a small amount of ethyl acetate, the filtrates were combined, concentrated and purified by column chromatography to give compound P7(3.12g, 66% yield). 473.2[ M + H ] M/z]+。
Calculated value C of element content (%) of Compound P734H20N2O: wherein C: 86.42, respectively; h: 4.27; n: 5.93; o: 3.39. measured value C34H20N2O: wherein C: 86.44; h: 4.26; n: 5.90 of; o: 3.40.
Figure BDA0002347907220000152
synthesis example 4
40g of polyphosphoric acid is added into a reaction bottle, heating is started, when the temperature is raised to 100 ℃, 4.05g of raw material 8a (11mmol, CAS No: 42824-53-3) and 4.2g of raw material A (20mmol) are sequentially added into the reaction bottle, the temperature is continuously raised to 150 ℃, and the reaction is carried out under the condition of heat preservation. Stopping the reaction when the reaction of the raw materials is completed by liquid phase monitoring, cooling the reaction solution to below 50 ℃, slowly adding water into the reaction solution, starting stirring, filtering, adjusting the pH value to be alkalescent (9-10) by using a sodium hydroxide aqueous solution (the mass fraction is 40%), extracting for 2 times by using ethyl acetate, separating the liquid, and combining organic phases. The organic phase was washed with water to neutrality, dried l h over anhydrous sodium sulfate, filtered to remove the drying agent to give a filter cake, which was rinsed with a small amount of ethyl acetate, the filtrates were combined, concentrated and purified by column chromatography to give compound P8(2.5g, 35% yield). 717.2[ M + H ] M/z]+。
Calculated value C of the content of element P850H28N4O2: wherein C: 83.78, respectively; h: 3.94; n: 7.82; o: 4.46. measured value C50H28N4O2: wherein C: 83.70, respectively; h: 3.96; n: 7.84; o: 4.50.
Figure BDA0002347907220000161
Synthesis examples 5 to 23
The nitrogen-containing compound was prepared in the same manner as in example 1, except that the starting material 1a in example 1 was replaced with the corresponding starting material Ia in Table 1, and the raw materials used, the correspondingly prepared compound, and the mass spectrum data are specifically shown in Table 1.
TABLE 1
Figure BDA0002347907220000162
Figure BDA0002347907220000171
Figure BDA0002347907220000181
Figure BDA0002347907220000191
The following synthetic preparation examples 1 to 15 are provided to illustrate the synthetic methods of preparing a part of the raw material Ia for the nitrogen-containing compound of the above synthetic examples. For ease of description, the compounds employed in the preparation of starting material Ia are represented by Ia-number numbers, e.g., 5a-1, 5a-2 respectively represent the compounds used in the preparation of starting material 5 a.
Synthesis production example 1 (raw Material 5a used in Synthesis example 20)
(1) Adding raw materials 5a-1(100mmol) and 200.0ml of DMF into a reaction bottle, starting stirring, reducing the temperature to-5 ℃ to 0 ℃, adding NBS (105mmol) in 4 batches, keeping the temperature for 2 hours, adding 200.0ml of dichloromethane and 200.0ml of water, stirring, standing, separating liquid, extracting the water phase with 100.0ml of dichloromethane, combining the organic phase, washing with water for 2 times, drying the organic phase with 5g of anhydrous sodium sulfate, concentrating the organic phase to the residual 30ml, cooling to room temperature, filtering to obtain 5a-2(60mmol), and obtaining the yield of 60%.
Figure BDA0002347907220000201
(2) 5a-2(50mmol), 5a-3 (55mmol) and potassium carbonate (100mmol) are sequentially added into a three-neck flask provided with a thermometer and a condenser tube, then 100ml of toluene, 20ml of ethanol and 20ml of water are sequentially added, the air in the reaction flask is replaced by nitrogen, and Pd (PPh) is added under the protection of nitrogen3)4(0.5mmol), starting heating, magnetically stirring, heating to 65-70 ℃, reacting for 6h, adding 30ml of water, cooling to room temperature, filtering, leaching a filter cake with 20ml of ethanol to obtain 5a-4(45mmol), wherein the yield is 90%.
Figure BDA0002347907220000202
(3) Adding raw materials 5a-4(40mmol) and 200.0ml of DMF into a reaction bottle, starting stirring, reducing the temperature to-5 ℃ to 0 ℃, adding NBS (44mmol) in 4 batches, keeping the temperature for 2 hours, adding 200.0ml of dichloromethane and 200.0ml of water, stirring, standing, separating, extracting the aqueous phase with 100.0ml of dichloromethane, combining the organic phases, washing with water for 2 times, drying the organic phase with 5g of anhydrous sodium sulfate, concentrating the organic phase to the residual 20ml, cooling to room temperature, filtering to obtain 5a-5(38mmol), and obtaining the yield of 95%.
Figure BDA0002347907220000211
(4) 5a-5(35mmol), 5a-6 (40mmol) and potassium carbonate (70mmol) are sequentially added into a three-neck flask provided with a thermometer and a condenser tube, then 80ml of toluene, 20ml of ethanol and 20ml of water are sequentially added, the air in the reaction flask is replaced by nitrogen, and Pd (PPh) is added under the protection of nitrogen3)4(0.3mmol), start heating, stir by magnetic forceStirring, heating to 65-70 ℃, reacting for 4h, adding 20ml of water, cooling to room temperature, filtering, leaching a filter cake with 20ml of ethanol to obtain 5a-7(24.5mmol), wherein the yield is 70%.
Figure BDA0002347907220000212
(5) After nitrogen replacement is carried out in a three-mouth reaction bottle provided with a mechanical stirring device, a thermometer and a constant pressure dropping funnel, 5a-7(20mmol) and 40.0ml THF are sequentially added, stirring is started, the temperature is reduced to-85 to-90 ℃, 2mol/L n-butyl lithium (24mmol) is dropwise added, the temperature in the dropwise adding process is kept at-85 to-90 ℃, the temperature is kept for 0.5h after the dropwise adding is finished, DMF (26mmol) is dropwise added, and the temperature is kept for 0.5h after the dropwise adding is finished. Pouring the reaction solution into 0.5mol/L diluted hydrochloric acid, extracting with 30.0ml toluene, separating, extracting the water phase with 20.0ml toluene for 1 time, combining the organic phases, washing with 20.0ml water for 2 times, separating, adding 1g anhydrous sodium sulfate into the organic phase, drying, filtering, concentrating the organic phase to be not discharged (0.08 to-0.09 MPa, 55 to 65 ℃), adding 10.0ml petroleum ether, filtering to obtain 5a-8(18mmol), wherein the yield is 90%.
Figure BDA0002347907220000221
(6) Raw materials 5a-8(15mmol), tetrahydrofuran 20.0ml, water 5ml and concentrated hydrochloric acid 1ml are added into a reaction bottle, stirring is started, sodium hypochlorite (22.5mmol) is added into 2 batches, reaction is carried out for 2 hours, water 50.0ml is added, and filtration is carried out to obtain 5a (12mmol) with yield of 80%.
Figure BDA0002347907220000222
Synthesis preparation examples 2 to 8
The starting material Ia in Table 2 was prepared by referring to the methods of step (5) and step (6) in Synthesis preparation example 1, except that the starting materials 5a to 7 in Synthesis example 1 were replaced with the corresponding starting materials Ia to 7 in Table 2.
TABLE 2
Figure BDA0002347907220000223
Figure BDA0002347907220000231
Synthesis preparation examples 9 to 15
Synthesis preparations 9 to 11 the starting material Ia in Table 3 was prepared by referring to the procedures from step (4) to step (6) in Synthesis preparation 1, except that 5a-5 in Synthesis preparation 1 was replaced with the corresponding Ia-5, 5a-6 in Table 3, and Ia-6 was replaced.
Synthesis preparations 12 to 13 starting material Ia was prepared by referring to the methods of step (2), step (4), step (5) and step (6) in Synthesis preparation 1, except that 5a-2 in Synthesis preparation 1 was replaced with the corresponding Ia-2 in Table 3, 5a-3 was replaced with Ia-3, and 5a-6 was replaced with Ia-6.
Synthetic production example 14 the starting material Ia was prepared by referring to the methods from step (2) to step (6) in synthetic production example 1, except that 5a-3 in synthetic production example 1 was replaced with the corresponding Ia-3 in Table 3.
Synthetic production example 15 the starting material Ia was prepared by referring to the procedures from step (2) to step (6) in synthetic production example 1, except that 5a-2 in synthetic production example 1 was replaced with the corresponding Ia-2, 5a-3 in Table 3, and Ia-3 was replaced.
TABLE 3
Figure BDA0002347907220000241
Figure BDA0002347907220000251
Application examples 1 to 23 are intended to illustrate the use of the nitrogen-containing compound of the present invention in an electron transport layer in an organic electroluminescent device.
Application example 1
A method of manufacturing an organic light emitting device, comprising the steps of:
(1) firstly, distilled water and methanol are sequentially used for ultrasonic cleaning
Figure BDA0002347907220000252
Drying a glass bottom plate of an Indium Tin Oxide (ITO) electrode;
(2) cleaning the anode base plate for 5 minutes by using oxygen plasma, and then loading the cleaned anode base plate into vacuum deposition equipment;
(3) the compound 2T-NATA (CAS: 185690-41-9) was vacuum deposited on the ITO electrode
Figure BDA0002347907220000253
A hole injection layer HIL with a thickness, and NPB (N, N '-diphenyl-N, N' -di (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine) is deposited on the hole injection layer in vacuum
Figure BDA0002347907220000254
A hole transport layer HTL with a thickness, and TCTA (with a structure shown in formula A) is evaporated on the hole transport layer to form
Figure BDA0002347907220000255
Electron blocking layer EBL of thickness. The host emitter ADN (CAS: 122648-99-1) and dopant BCzVB (CAS: 62608-15-5) were then mixed at a ratio of 96: 4 are co-deposited on the hole transport region
Figure BDA0002347907220000256
A light emitting layer EML of thickness;
Figure BDA0002347907220000261
(4) will be provided with
Figure BDA0002347907220000262
A hole blocking layer BCP (CAS: 4733-39-5) with the thickness is deposited on the light-emitting layer in a vacuum mode to form the hole blocking layer;
(5) vacuum depositing compound P1 on the hole blocking layer to form
Figure BDA0002347907220000263
Electron transport layer of thickness and formation of LiQ (8-hydroxyquinoline-lithium) by vapor deposition on the electron transport layer
Figure BDA0002347907220000264
Electron injection layer EIL of thickness, then magnesium (Mg) and silver (Ag) were mixed at a ratio of 1: 9 is vacuum-evaporated on the electron injection layer to form
Figure BDA0002347907220000265
A cathode of thickness. The thickness of the cathode as a vapor deposition is set to
Figure BDA0002347907220000266
CP-1 (structure shown below), and a capping layer (CPL) was formed, thereby completing the fabrication of an organic light emitting device, and the fabricated device was denoted as a 1.
Figure BDA0002347907220000267
Application examples 2 to 23
Organic electroluminescent devices a2 to a23 were produced by the methods of application example 1, respectively, except that the compound P1 in step (5) was replaced with the nitrogen-containing compound produced in the synthesis examples, respectively.
Comparative example 1
An organic electroluminescent device was produced in the same manner as in application example 1, except that the compound P1 as an electron transport layer material was changed to the compound A (Alq)3) Instead, an organic electroluminescent device D1 was thus produced. Alq3The structural formula of (A) is as follows:
Figure BDA0002347907220000271
comparative example 2
An organic electroluminescent device was produced in the same manner as in application example 1, except that compound P1 as an electron transport layer material was replaced with compound B (2-NPIP), thereby producing organic electroluminescent device D2. The structural formula of compound B is shown below:
Figure BDA0002347907220000272
test example
The organic electroluminescent devices A1-A23, D1 and D2 prepared as above were controlled at 15mA/cm2The life of the T95 device was tested under the condition that the data voltage, efficiency and color coordinate are 10mA/cm at constant current density2The following tests were carried out and the test results are shown in Table 4.
TABLE 4
Figure BDA0002347907220000273
Figure BDA0002347907220000281
The driving voltages of the organic electroluminescent devices A1 to A23 prepared in application examples 1 to 23 were between 3.8 and 4.1V, which are about 7 to 14% lower than the driving voltages (average value of 4.4) of the comparative organic electroluminescent devices D1 to D2. The luminous efficiency of the devices A1-A23 is 5.7-6.8 Cd/A, and is 9.6-31% higher than that of D2 with higher comparative luminous efficiency; the external quantum efficiency of A1-A23 is 11.3-13.2%, which is 5-25% higher than that of D2 with higher external quantum efficiency in comparison. The service life of T95 of A1-A23 is 169-278 h, which is at least 34% longer than that of D1 of the device in comparison with 1 and at least 12% longer than that of D2 of the device in comparison with 2. In addition, the driving voltages of a1 to a23 were lower than D1 of comparative example 1, comparable to or even lower than D2 of comparative example 2.
It can be seen that the organic electroluminescent devices prepared in application examples 1 to 23 have higher luminous efficiency, higher external quantum efficiency, and lower driving voltage, compared to the comparative examples 1 to 2. In addition, as an electron transport layer material, the nitrogen-containing compound of the present invention has a longer lifetime than that of the comparative example, and can significantly improve the performance of an organic electroluminescent device when used in an electron transport layer of the organic electroluminescent device.
The preferred embodiments of the present invention have been described in detail with reference to the accompanying drawings, however, the present invention is not limited to the specific details of the above embodiments, and various simple modifications can be made to the technical solution of the present invention within the technical idea of the present invention, and these simple modifications are within the protective scope of the present invention.
It should be noted that the various technical features described in the above embodiments can be combined in any suitable manner without contradiction, and the invention is not described in any way for the possible combinations in order to avoid unnecessary repetition.
In addition, any combination of the various embodiments of the present invention is also possible, and the same should be considered as the disclosure of the present invention as long as it does not depart from the spirit of the present invention.

Claims (10)

1. A nitrogen-containing compound characterized by having a structure represented by the following formula (1) or formula (2):
Figure FDA0002347907210000011
wherein Ar is selected from substituted or unsubstituted aryl with 6-60 carbon atoms, or substituted or unsubstituted heteroaryl with 2-60 carbon atoms; l is selected from arylene with 12-40 carbon atoms;
the substituent of Ar is selected from deuterium, halogen, cyano, alkyl with 1-6 carbon atoms or a group shown as a formula (1-1):
Figure FDA0002347907210000012
2. the nitrogen-containing compound according to claim 1, wherein Ar has one or more substituents each independently selected from a cyano group and/or an alkyl group having 1 to 4 carbon atoms.
3. The nitrogen-containing compound according to claim 1 or 2, wherein L is an arylene group having 12 to 25 carbon atoms.
4. The nitrogen-containing compound of claim 1, wherein L is selected from the group consisting of:
Figure FDA0002347907210000013
5. the nitrogen-containing compound according to claim 1, wherein Ar is selected from a substituted or unsubstituted aryl group having 6 to 45 carbon atoms, or a substituted or unsubstituted heteroaryl group having 8 to 45 carbon atoms;
preferably, Ar is selected from substituted or unsubstituted aryl groups having 18 to 42 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12 to 42 carbon atoms.
6. The nitrogen-containing compound according to claim 1, wherein Ar is selected from the group consisting of:
Figure FDA0002347907210000021
7. the nitrogen-containing compound according to claim 1, wherein the nitrogen-containing compound is selected from at least one of the following compounds P1-P80:
Figure FDA0002347907210000031
Figure FDA0002347907210000041
Figure FDA0002347907210000051
Figure FDA0002347907210000061
8. use of the nitrogen-containing compound of any one of claims 1 to 7 in an organic electroluminescent device.
9. The use according to claim 8, wherein the nitrogen-containing compound is used as an electron transport layer material of the organic electroluminescent device.
10. An organic electroluminescent device comprising an anode, a cathode, and at least one functional layer interposed between the anode and the cathode, the functional layer comprising a hole injection layer, a hole transport layer, an organic electroluminescent layer, an electron transport layer, and an electron injection layer, characterized in that the electron transport layer contains the nitrogen-containing compound according to any one of claims 1 to 7.
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