CN115643767A - Organic electroluminescent device, display device, light source device, and electronic product - Google Patents
Organic electroluminescent device, display device, light source device, and electronic product Download PDFInfo
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Abstract
The present invention provides an organic electroluminescent device comprising: a first electrode, a second electrode, and at least one layer of a first organic film disposed between the first electrode and the light emitting layer; the first organic film comprises a light-emitting auxiliary layer, and the material of the light-emitting auxiliary layer comprises a material containing triarylamine and a heteroaryl structural unit; at least one second organic film disposed between the light emitting layer and a second electrode; the second organic film includes an electron transport layer, and a material of the electron transport layer includes a material containing triazine and biphenyl units. The organic electroluminescent device has lower working voltage, higher BI luminous efficiency and longer service life.
Description
Technical Field
The present disclosure relates to an organic electroluminescent device, and more particularly, to an organic electroluminescent device, a display device, a light source device, and an electronic product, and belongs to the field of organic optoelectronics.
Background
An Organic Light-Emitting Diode (OLED) is used for short. The light emitting device has a feature of being thin and capable of emitting light with high luminance at a low driving voltage and emitting light in multiple colors by selecting a light emitting material, and thus has attracted attention.
Since the research revealed that the organic thin film element can emit light with high brightness by c.w.tang et al of kodak corporation, a lot of research and progress has been made on its application by a large number of researchers in the OLED industry. Organic thin film light emitting devices are widely used in various main displays and the like, and their practical use has been advanced. However, there are many technical problems, and among them, efficient use of light emission and reduction of light emission loss are significant problems.
The OLED can be classified into a bottom emission organic light emitting device and a top emission organic light emitting device according to a light emitting manner of the OLED. The initial OLEDs were bottom-emitting devices, which were constructed from top to bottom as follows: opaque metal cathode/organic functional layer/transparent anode, light exits from the anode and is called bottom emission. Top-emitting OLEDs refer to OLEDs where light exits the top of the device. The top-emitting OLED is not influenced by whether the substrate is transparent or not, so that the aperture opening ratio of the display panel can be effectively improved, the design of a TFT circuit on the substrate is expanded, the selection of electrode materials is enriched, and the integration of a device and the TFT circuit is facilitated. If the device emits light in a bottom emission manner, the light is blocked by TF and metal wiring on the substrate when passing through the substrate, which affects the actual light emitting area. If the light rays are emitted from the upper part of the device, and a top emission device structure is adopted, the light emitting area of the device cannot be influenced by the circuit design of the substrate, the working voltage of the OLED is lower under the same brightness, and the longer service life can be obtained. Therefore, top-emitting devices are the first choice for small pixel, high PPI, small screen active displays such as cell phones.
The planar OLED material structure is adopted in the industry all the time, so that the mobility of the material can be improved to a certain degree, the working voltage is reduced, the evaporation temperature of the material can be increased, and the evaporation difficulty of the process is increased. Especially, the luminous auxiliary layer and the transmission layer are made of materials, so that the evaporation temperature of the material process is reduced, reasonable materials are matched, the yield improvement of a display screen of a panel manufacturer can be effectively relieved, the luminous efficiency of a device is further improved, and the service life of the device is further prolonged.
Disclosure of Invention
The invention provides an organic electroluminescent device, a display device, a light source device and an electronic product. The organic electroluminescent device has lower working voltage, higher BI luminous efficiency and longer service life.
In order to realize the purpose of the invention, the technical scheme of the invention is as follows:
the present invention provides an organic electroluminescent device,
the method comprises the following steps:
a first electrode for forming a first electrode layer on a substrate,
a second electrode, and
at least one first organic film disposed between the first electrode and the light emitting layer;
the first organic film comprises a light-emitting auxiliary layer, and the material of the light-emitting auxiliary layer comprises a material containing triarylamine and a heteroaryl structural unit;
at least one second organic film disposed between the light emitting layer and a second electrode;
the second organic film includes an electron transport layer, and a material of the electron transport layer includes a material containing triazine and biphenyl units.
Preferably, the material of the luminescence auxiliary layer comprises a material containing triarylamine and heteroaryl structural units, as shown in the following formula I:
formula I
Wherein X is selected from O atom, S atom or N-R 6 Or C-R 7 R 8 Wherein R is 6 、R 7 And R 8 Each independently selected from substituted or unsubstituted alkyl chains, C6-C30 aryl;
L 1 -L 2 each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl;
Ar 1 selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl;
R 1 -R 5 each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl.
More preferably, the material of the luminescence auxiliary layer is represented by formula II:
formula II
Wherein R is 2 -R 5 、L 1 -L 2 、Ar 1 And X is as defined above.
More preferably, said L 1 -L 2 Each independently selected from a single bond, phenylene, naphthylene, phenanthrylene, biphenylene, or pyridylene.
Preferably, when the substituted or unsubstituted C6-C30 aryl group, the substituted or unsubstituted C5-C30 heteroaryl group contains a substituent, the substituent is at least one selected from deuterium, halogen, cyano, silyl, unsubstituted or halogenated C1-C15 linear or branched alkyl group, unsubstituted or halogenated C1-C15 alkoxy group, C1-C15 alkylthio group, C6-C24 aryl group, C2-C24 heteroaryl group or C6-C18 arylamine group.
Preferably, the material of the luminescence auxiliary layer comprises a material containing a structural unit of triarylamine and heteroaryl, and is selected from any one or a combination of at least two of the following materials:
preferably, the material of the electron transport layer comprises a material containing triazine and biphenyl structural units, as shown in formula III below:
formula III
Wherein, Y 1 -Y 3 Each independently selected from a N atom or a C atom;
L 3 selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl;
Ar 2 selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl;
R 9 and R 10 Each selected from the group consisting of unsubstituted or halogenated C1-C15 linear or branched alkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C5-C30 heteroaryl groups.
Preferably, L 3 Selected from substituted or unsubstituted phenylene, naphthylene, phenanthrylene, biphenylene, anthracylene, 17627ylene, pyridylene, quinolylene or isoquinolylene, etc..
Preferably, when the substituted or unsubstituted C6-C30 aryl group, the substituted or unsubstituted C5-C30 heteroaryl group contains a substituent, the substituent is at least one selected from deuterium, halogen, cyano, silyl, unsubstituted or halogenated C1-C15 linear or branched alkyl group, unsubstituted or halogenated C1-C15 alkoxy group, C1-C15 alkylthio group, C6-C24 aryl group, C2-C24 heteroaryl group or C6-C18 arylamine group.
Preferably, the material of the electron transport layer comprises a material containing triazine and biphenyl structural units, and is selected from any one or a combination of at least two of the following materials:
preferably, the first organic film further includes at least one of a light emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, and an electron injection layer.
Preferably, the second organic film further includes at least one of a light emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, and an electron injection layer.
The invention also provides a display device comprising the organic electroluminescent device.
The invention also provides a light source device comprising the organic electroluminescent device.
The invention also provides an electronic product comprising the organic electroluminescent device.
Detailed Description
It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive.
The disclosure may be understood more readily by reference to the following detailed description and the examples included therein.
Before the present compounds, devices, and/or methods are disclosed and described, it is to be understood that they are not limited to the particular synthetic methods (otherwise specified), or to the particular reagents (otherwise specified), as such can, of course, vary. It is also to be understood that the terminology used herein is for the purpose of describing particular aspects only and is not intended to be limiting. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing, the exemplary methods and materials are described below.
In a preferred embodiment of the present invention, the OLED device according to the invention comprises a hole transport layer, which may preferably be selected from known or unknown materials, particularly preferably from the following structures, without representing the present invention being limited to the following structures:
in a preferred embodiment of the present invention, the hole transport layer contained in the OLED device of the present invention comprises one or more p-type dopants. Preferred p-type dopants of the present invention are, but do not represent a limitation of the present invention to:
the linking atom used in the present invention can link two groups, for example, N and C groups. The linking atom can optionally (if valency permits) have other chemical moieties attached. For example, in one aspect, oxygen does not have any other chemical group attached because once bonded to two atoms (e.g., N or C) valences have been satisfied. Conversely, when carbon is a linking atom, two additional chemical moieties can be attached to the carbon atom. Suitable chemical moieties include, but are not limited to, hydrogen, hydroxyl, alkyl, alkoxy, = O, halogen, nitro, amine, amide, mercapto, aryl, heteroaryl, cycloalkyl, and heterocyclyl.
The term "substituted" as used herein is intended to encompass all permissible substituents of organic compounds. In a broad aspect, permissible substituents include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, and aromatic and nonaromatic substituents of organic compounds. Illustrative substituents include, for example, those described below. The permissible substituents can be one or more, identical or different for suitable organic compounds. For the purposes of the present invention, a heteroatom (e.g. nitrogen) can have a hydrogen substituent and/or any permissible substituents of organic compounds described herein which satisfy the valences of the heteroatom. The present disclosure is not intended to be limited in any way by the permissible substituents of organic compounds. Likewise, the term "substituted" or "substituted with" includes the implicit proviso that such substitution is consistent with the atom being substituted and the allowed valence of the substituent, and that the substitution results in a stable compound (e.g., a compound that does not spontaneously undergo transformation (e.g., by rearrangement, cyclization, elimination, etc.)). It is also contemplated that, in certain aspects, individual substituents can be further optionally substituted (i.e., further substituted or unsubstituted), unless explicitly stated to the contrary.
In defining the terms, "R 1 ”、“R 2 ”、“R 3 ”、“R 4 ”、“R 5 ”、“R 6 ”、“R 7 ”、“R 8 ”、“R 9 "and" R 10 "used as a general symbol in the present invention denotes various specific substituents. These symbols can be any substituent, are not limited to those disclosed herein, and when they are defined as certain substituents in one instance, they can be defined as some other substituents in other instances.
The term "alkyl" as used herein is a branched or unbranched saturated hydrocarbon group of 1 to 24 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, neopentyl, hexyl, heptyl, half-yl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, eicosyl, tetracosyl and the like. The alkyl group may be cyclic or acyclic. The alkyl group may be branched or unbranched. The alkyl group may also be substituted or unsubstituted. For example, the alkyl group may be substituted with one or more groups including, but not limited to, optionally substituted alkyl, cycloalkyl, alkoxy, amino, halo, hydroxy, nitro, silyl, sulfo-oxo, or thiol as described herein. A "lower alkyl" group is an alkyl group containing 1 to 6 (e.g., 1 to 4) carbon atoms.
Throughout the specification, "alkyl" is generally used to refer to both unsubstituted alkyl and substituted alkyl; however, substituted alkyl groups are also specifically mentioned in the present invention by identifying specific substituents on the alkyl group. For example, the term "halogenated alkyl" or "haloalkyl" specifically refers to an alkyl substituted with one or more halogens (e.g., fluorine, chlorine, bromine, or iodine). The term "alkoxyalkyl" specifically refers to an alkyl group substituted with one or more alkoxy groups, as described below. The term "alkylamino" specifically refers to an alkyl group substituted with one or more amino groups, as described below, and the like. When "alkyl" is used in one instance and a specific term such as "alkyl alcohol" is used in another instance, it is not meant to imply that the term "alkyl" does not refer to the specific term such as "alkyl alcohol" or the like at the same time.
The term "aryl" as used herein is a group containing any carbon-based aromatic group including, but not limited to, phenyl, naphthyl, phenyl, biphenyl, phenoxyphenyl, anthracyl, phenanthryl, and the like. The term "aryl" also includes "heteroaryl," which is defined as a group containing an aromatic group having at least one heteroatom incorporated into the ring of the aromatic group. Examples of heteroatoms include, but are not limited to, nitrogen, oxygen, sulfur, and phosphorus. Likewise, the term "non-heteroaryl" (which is also included in the term "aryl") defines a group that contains an aromatic group that does not contain heteroatoms. The aryl group may be substituted or unsubstituted. The aryl group may be substituted with one or more groups including, but not limited to, alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, heteroaryl, aldehyde, amino, carboxyl, ester, halogen, hydroxyl, carbonyl, azido, nitro, silyl, thio-oxo (sulfo-oxo), or thiol as described herein. The term "biaryl" is a specific type of aryl group and is included in the definition of "aryl". Biaryl refers to two aryl groups joined together via a fused ring structure, as in naphthalene, or two aryl groups connected via one or more carbon-carbon bonds, as in biphenyl.
"R" used in the present invention 1 ”、“R 2 ”、“R 3 ”、“R 4 ”、“R 5 ”、“R 6 ”、“R 7 ”、“R 8 ”、“R 9 "and" R 10 "may independently have one or more of the groups listed above. For example, if R 1 Being a straight chain alkyl, then one hydrogen atom of the alkyl group may be optionally substituted with hydroxyl, alkoxy, alkyl, halogen, and the like. Depending on the group selected, the first group may be incorporated within the second group, or alternatively, the first group may be pendent, i.e., attached, to the second group. For example, for the phrase "alkyl group comprising an amino group," the amino group can be incorporated within the backbone of the alkyl group. Alternatively, the amino group may be attached to the backbone of the alkyl group. The nature of the selected group will determine whether the first group is intercalated or attached to the second group.
R is mentioned several times in the chemical structures and parts disclosed and described in the present application 1 、R 2 、R 3 、R 4 、R 5 、R 6 And so on. In the specification, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 Etc. are each applicable to the citation of R 1 、R 2 、R 3 、R 4 、R 5 、R 6 Etc., unless otherwise specified.
In the present invention, the organic photoelectric device is an anode which can be formed by depositing a metal or an oxide having conductivity and an alloy thereof on a substrate by a sputtering method, electron beam evaporation, vacuum evaporation, or the like; and sequentially evaporating a hole injection layer, a hole transport layer, a luminescent layer, an air barrier layer and an electron transport layer on the surface of the prepared anode, and then evaporating a cathode. The organic electroluminescent device is manufactured by sequentially evaporating the cathode, the organic layer and the anode on the external substrate by the method. The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, and an electron transport layer. In the invention, the organic layer is prepared by adopting a high polymer material according to a solvent engineering (spin-coating), tape-casting (tape-casting), doctor-blading (sector-coating), screen-printing (screen-printing), ink-jet printing or thermal-imaging (thermal-imaging) method instead of an evaporation method, so that the number of layers of the device can be reduced.
The materials used for the organic electroluminescent device according to the present invention may be classified as top emission, low emission, or double-sided emission. The compounds of the organic electroluminescent device according to the embodiment of the present invention can be applied to the aspects of organic solar cells, illuminating OLEDs, flexible OLEDs, organic photoreceptors, organic thin film transistors and other electroluminescent devices by a similar principle of the organic light emitting device.
Examples
The following examples of compound syntheses, compositions, devices, or processes are intended to be illustrative of general approaches to the industry and are not intended to limit the scope of the patent. Unless otherwise indicated, the weighing is carried out separately, at temperatures of ℃ or at ambient temperature and at pressures close to atmospheric pressure.
The following examples provide methods for the preparation of the novel compounds, but the preparation of such compounds is not limited to this method. In the art, the compounds claimed in this patent can be prepared by the methods listed below or by other methods, since they can be easily prepared by modification. The following examples are given by way of example only and are not intended to limit the scope of the patent. The temperature, catalyst, concentration, reactants, and course of reaction can all be varied to select different conditions for the preparation of the compound for different reactants.
Application example 1
(1) Q01 (6 mmol), Q02 (8 mmol), sodium t-butoxide (10 mmol) and toluene 200ml were purged with nitrogen, and pd was added 2 (dba) 3 (0.05 mmol) and Sphos (0.05 mmol), heating to 100-120 deg.C, refluxing for 6 hr, and stopping reaction. Cooling to 30-40 deg.C, adding 200ml water, and layering. After washing twice, toluene was concentrated and 100ml of n-heptane was added and the mixture was slurried. To obtain a target product A-013.
The structure of target product a-013 was tested: ESI-MS (m/z) (m +) was obtained by LC-MS analysis, theoretical 689.27 and test 689.84.
Application example 2
(1) Q03 (6 mmol), Q04 (8 mmol), sodium tert-butoxide (10 mmol) and toluene 200ml were purged with nitrogen, and pd was added 2 (dba) 3 (0.05 mmol) and Sphos (0.05 mmol), heating to 100-120 deg.C, refluxing for 6 hr, and stopping reaction. Cooling to 30-40 deg.C, adding 200ml water, and layering. After washing twice with water, toluene was concentrated and 100ml of n-heptane was added, followed by beating. To obtain a target product A-055.
Testing the structure of the target product a-055: ESI-MS (m/z) (μm +) was obtained by liquid chromatography-mass spectrometry analysis with a theoretical value of 689.27 and a test value of 689.85.
Application example 3
(1) Q03 (6 mmol), Q05 (8 mmol), sodium t-butoxide (10 mmol) and toluene 200ml were purged with nitrogen, and pd was added 2 (dba) 3 (0.05 mmol) and Sphos (0.05 mmol), heating to 100-120 deg.C, refluxing for 6 hr, and stopping reaction. Cooling to 30-40 deg.C, adding 200ml water, and layering. After washing twice with water, toluene was concentrated and 100ml of n-heptane was added, followed by beating. The target product A-057 is obtained.
The structure of the target product A-057 was tested: ESI-MS (m/z) (M +) was obtained by liquid chromatography-mass spectrometry analysis with a theoretical value of 689.27 and a test value of 689.84.
Application example 4
(1) Q01 (6 mmol), Q06 (8 mmol), sodium tert-butoxide (10 mmol), toluene 200ml, nitrogen substitution, then pd addition 2 (dba) 3 (0.05 mmol) and Sphos (0.05 mmol), heating to 100-120 deg.C, refluxing for 6 hr, and stopping reaction. Cooling to 30-40 deg.C, adding 200ml water, and layering. After washing twice with water, toluene was concentrated and 100ml of n-heptane was added, followed by beating. Obtaining a target product A-058.
The structure of the target product A-058 was tested: ESI-MS (m/z) (m +) was obtained by LC-MS analysis, theoretical 689.27 and test 689.84.
Application example 5
(1) Q01 (6 mmol), Q05 (8 mmol), sodium tert-butoxide (10 mmol) and toluene (200 ml) were replaced with nitrogen, and pd was added 2 (dba) 3 (0.05 mmol) and Sphos (0.05 mmol), heating to 100-120 deg.C, refluxing for 6 hr, and stopping reaction. Cooling to 30-40 deg.C, adding 200ml water, and layering. After washing twice, toluene was concentrated and 100ml of n-heptane was added and the mixture was slurried. Obtaining a target product A-059.
The structure of the target product A-059 was tested: ESI-MS (m/z) (m +) was obtained by liquid chromatography-mass spectrometry analysis with a theoretical value of 689.27 and a test value of 689.83.
Application example 6
(1) Q01 (6 mmol), Q07 (8 mmol), sodium t-butoxide (10 mmol) and toluene 200ml were purged with nitrogen, and pd was added 2 (dba) 3 (0.05 mmol) and Sphos (0.05 mmol), heating to 100-120 deg.C, refluxing for 6 hr, and stopping reaction. Cooling to 30-40 deg.C, adding 200ml water, and layering. After washing twice, toluene was concentrated and 100ml of n-heptane was added and the mixture was slurried. Obtaining a target product A-080.
The structure of the target product A-080 was tested: ESI-MS (m/z) (μm +) was obtained by liquid chromatography-mass spectrometry analysis, theoretical 765.30 and test 765.94.
Application example 7
(1) Q03 (6 mmol), Q08 (8 mmol), sodium t-butoxide (10 mmol) and toluene 200ml were purged with nitrogen, and pd was added 2 (dba) 3 (0.05 mmol) and Sphos (0.05 mmol), heating to 100-120 deg.C, refluxing for 6 hr, and stopping reaction. Cooling to 30-40 deg.C, adding 200ml water, and layering. After washing twice with water, toluene was concentrated and 100ml of n-heptane was added, followed by beating. Obtaining a target product A-089.
The structure of the target product A-089 was tested: ESI-MS (m/z) (M +) was obtained by liquid chromatography-mass spectrometry combined analysis with a theoretical value of 694.30 and a test value of 694.87.
Application example 8
(1) Q01 (6 mmol), Q09 (8 mmol), sodium tert-butoxide (10 mmol) and toluene 200ml were purged with nitrogen, and pd was added 2 (dba) 3 (0.05 mmol) and Sphos (0.05 mmol), heating to 100-120 deg.C, refluxing for 6 hr, and stopping reaction. Cooling to 30-40 deg.C, adding 200ml water, and layering. After washing twice with water, toluene was concentrated and 100ml of n-heptane was added, followed by beating. Obtaining a target product A-091.
Testing the structure of the target product A-091: ESI-MS (m/z) (M +) was obtained by liquid chromatography-mass spectrometry analysis with theoretical value of 696.32 and test value of 696.88.
Application example 9
(1) P01 (6 mmol), P02 (8 mmol), pd (dppf) Cl 2 (0.05mmol) 、K 2 CO 3 (9 mmol) Dioxane was added: water (4The reaction mixture was put into a 50mL flask and refluxed for 24 hours. Cooled to room temperature, and then saturated MgSO was slowly added to the solution 4 The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to column chromatography by removing the solvent through a rotary evaporator to obtain a crude product B-004.
The structure of target product B-004 was tested: LC-MS (m/z) (M +) was obtained by LC-MS mass spectrometry with a theoretical value of 613.25 and a test value of 613.75.
Application example 10
(1) P01 (6 mmol), P03 (8 mmol), pd (dppf) Cl 2 (0.05mmol) 、K 2 CO 3 (9 mmol) Dioxane was added: water (4. Cooled to room temperature, and then saturated MgSO was slowly added to the solution 4 The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to column chromatography by removing the solvent through a rotary evaporator to obtain a crude product B-010.
And (3) testing the structure of a target product B-010: LC-MS (m/z) (m +) was obtained by LC-MS combined with mass spectrometry, with a theoretical value of 663.27 and a test value of 663.81.
Application example 11
(1) P01 (6 mmol), P04 (8 mmol), pd (dppf) Cl 2 (0.05mmol) 、K 2 CO 3 (9 mmol) Dioxane was added: water (4. After cooling to room temperature, saturated aqueous MgSO4 solution and ethyl acetate were slowly added to the solution to extract three times, and then the organic layer was subjected to solvent removal by a rotary evaporator and column chromatography to obtain a crude product B-022.
The structure of target product B-022 was tested: LC-MS (m/z) (μm +) was obtained by LC-MS combined analysis with a theoretical value of 689.28 and a test value of 689.84.
Application example 12
(1) P05 (6 mmol), P02 (8 mmol), pd (dppf) Cl 2 (0.05mmol) 、K 2 CO 3 (9 mmol) dioxane was added: water (4. Cooling to room temperature, then slowly adding saturated MgSO4 aqueous solution and ethyl acetate into the solution, extracting three times, then removing the solvent from the organic layer by a rotary evaporator, and performing column chromatography to obtain a crude product B-051.
And (3) testing the structure of a target product B-051: LC-MS (m/z) (m +) was analyzed by liquid chromatography-mass spectrometry to have a theoretical value of 765.31 and a test value of 765.94.
Application example 13
(1) P01 (6 mmol), P06 (8 mmol), pd (dppf) Cl 2 (0.05mmol) 、K 2 CO 3 (9 mmol) Dioxane was added: water (4. Cooled to room temperature, and then saturated MgSO was slowly added to the solution 4 The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to column chromatography by removing the solvent through a rotary evaporator to obtain a crude product B-057.
The structure of the target product B-057 was tested: LC-MS (m/z) (μm +) was obtained by LC-MS mass spectrometry with a theoretical value of 618.28 and a test value of 618.78.
Application example 14
(1) P01 (6 mmol), P07 (8 mmol), pd (dppf) Cl 2 (0.05mmol) 、K 2 CO 3 (9 mmol) dioxane was added: water (4. Cooled to room temperature, and then saturated MgSO was slowly added to the solution 4 The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to column chromatography by removing the solvent through a rotary evaporator to obtain a crude product B-072.
And (3) testing the structure of a target product B-072: LC-MS (m/z) (m +) was obtained by LC-MS combined analysis with a theoretical value of 668.30 and a test value of 668.84.
The following are some examples of applications of the organic compounds of the present invention in OLED devices:
the preparation method of the OLED device comprises the following specific steps:
application example 1
The alkali-free glass substrate was first washed with an ultrasonic cleaner using isopropyl alcohol for 15 minutes, and then subjected to UV ozone washing treatment in air for 30 minutes. The treated substrate was subjected to vacuum deposition by first depositing ITO/Ag/ITO at 100nm as an anode, and then depositing a hole injection layer (HATCN, 50 nm), a hole transport layer (NPB, 30 nm), a light-emitting auxiliary layer (inventive compound a-013, 45 nm), a blue light-emitting layer (host ADN and doped BD (weight ratio 95: 5, 30 nm), an electron transport layer (ET 1: liq =1, 30 nm), and an electron injection layer (LiF, 0.5 nm) in this order, followed by co-deposition of Mg and Ag (weight ratio 10: 1, 15 nm) to prepare a translucent cathode, then depositing compound CPL (65 nm) as a capping layer, and finally encapsulating the light-emitting device with an epoxy resin adhesive under a nitrogen atmosphere.
Application examples 2-8, the only difference from application example 1 is that: replacing compound A-013 with compound A-055, compound A-057, compound A-058, compound A-059, compound A-080, compound A-089, compound A-091; the other preparation steps are the same.
Comparative example 1, differing from application example 1 only in that: compound A-013 was replaced with comparative compound BP1, and the other preparation steps were identical.
Examples 9-14, which differed from comparative example 1 only in that: replacing the electron transport compound ET with a compound B-004, a compound B-010, a compound B-022, a compound B-051, a compound B-057 and a compound B-072; the other preparation steps are the same.
Application examples 15 to 24, the light-emitting auxiliary layer was replaced with compound a-013, and the electron-transporting layer was replaced with compound B-004, compound B-010, compound B-022, compound B-051, compound B-057, compound B-072, respectively; the other preparation steps are the same.
Application example 25-31, electron transport compound ET was replaced with compound B-004, while the luminescence-assist layer was replaced with compound a-055,; the other preparation steps are the same.
Application examples 32-34, the electron transport compound ET was replaced with compound B-051 and compound B-057, while the light-emitting auxiliary layer was replaced with compound a-057 and compound a-059; the other preparation steps are the same.
Comparative example 1 and comparative example 2, the only differences from application example 1 are: compound A-013 was replaced with comparative compound 1 and comparative compound 2, compound A-057, compound A-058, compound A-059, compound A-080, compound A-089, compound A-091, and the other preparation steps were the same.
Comparative compound 1 and comparative compound 2 have the following structures:
comparative Compound 1 comparative Compound 2
TABLE 1
As can be seen from the test data of table 1, the application examples of the compound of the present invention have lower operating voltage, higher BI luminous efficiency and longer service life than comparative examples 1 to 4. When only the compound of the present invention is used as a luminescence auxiliary layer or an electron transport layer, the compounds of the present invention, corresponding to application examples 1 to 18, exhibit a lower operating voltage, a higher BI luminescence efficiency and a longer service life. When the compound of the present invention is used as a luminescence auxiliary layer and an electron transport layer, the compounds of the present invention corresponding to application examples 19 to 34 exhibit a lower operating voltage, a higher BI luminescence efficiency and a longer lifetime.
Claims (15)
1. An organic electroluminescent device having a first electrode and a second electrode,
the method comprises the following steps:
a first electrode for forming a first electrode layer on a substrate,
a second electrode, and
at least one first organic film disposed between the first electrode and the light emitting layer;
the first organic film comprises a light-emitting auxiliary layer, and the material of the light-emitting auxiliary layer comprises a material containing triarylamine and a heteroaryl structural unit;
at least one second organic film disposed between the light emitting layer and a second electrode;
the second organic film includes an electron transport layer, and a material of the electron transport layer includes a material containing triazine and biphenyl units.
2. The organic electroluminescent device as claimed in claim 1, wherein the material of the luminescence auxiliary layer comprises a material containing triarylamine and heteroaryl structural units, as shown in formula I below:
formula I
Wherein X is selected from O atom, S atom or N-R 6 Or C-R 7 R 8 Wherein R is 6 、R 7 And R 8 Each independently selected from substituted or unsubstituted alkyl chains, C6-C30 aryl;
L 1 -L 2 each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl;
Ar 1 selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl;
R 1 -R 5 each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl.
3. The organic electroluminescent device of claim 2, wherein the material of the light-emitting auxiliary layer is represented by formula II:
formula II
Wherein R is 2 -R 5 、L 1 -L 2 、Ar 1 And X is the same as described in claim 2.
4. The organic electroluminescent device according to claim 2, wherein L is L 1 -L 2 Each independently selected from a single bond, phenylene, naphthylene, phenanthrylene, biphenylene, or pyridylene.
5. The organic electroluminescent device according to claim 2, wherein when the substituted or unsubstituted C6-C30 aryl group, the substituted or unsubstituted C5-C30 heteroaryl group has a substituent, the substituent is selected from at least one of deuterium, halogen, cyano group, silane group, unsubstituted or halogenated C1-C15 linear or branched alkyl group, unsubstituted or halogenated C1-C15 alkoxy group, C1-C15 alkylthio group, C6-C24 aryl group, C2-C24 heteroaryl group, or C6-C18 arylamine group.
6. The organic electroluminescent device according to claim 1, wherein the material of the luminescence auxiliary layer comprises a material containing a structural unit of triarylamine and heteroaryl, and is selected from any one or a combination of at least two of the following materials:
7. the organic electroluminescent device of claim 1, wherein the material of the electron transport layer comprises a material comprising triazine and biphenyl structural units, as shown in formula III below:
formula III
Wherein, Y 1 -Y 3 Each independently selected from a N atom or a C atom;
L 3 selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl;
Ar 2 selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl;
R 9 and R 10 Each selected from the group consisting of unsubstituted or halogenated C1-C15 linear or branched alkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C5-C30 heteroaryl groups.
8. The organic electroluminescent device of claim 7, wherein L is 3 Selected from substituted or unsubstituted phenylene, naphthylene, phenanthrylene, biphenylene, anthracylene, 17627ylene, pyridylene, quinolylene or isoquinolylene, etc..
9. The organic electroluminescent device according to claim 7, wherein when the substituted or unsubstituted C6-C30 aryl group, the substituted or unsubstituted C5-C30 heteroaryl group has a substituent, the substituent is selected from at least one of deuterium, halogen, cyano, silyl, unsubstituted or halogenated C1-C15 linear or branched alkyl group, unsubstituted or halogenated C1-C15 alkoxy group, C1-C15 alkylthio group, C6-C24 aryl group, C2-C24 heteroaryl group, or C6-C18 arylamine group.
10. The organic electroluminescent device according to claim 1, wherein the material of the electron transport layer comprises a material containing triazine and biphenyl structural units, selected from any one or a combination of at least two of the following materials:
11. the organic electroluminescent device according to claim 1, wherein the first organic film further comprises at least one of a light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, and an electron injection layer.
12. The organic electroluminescent device according to claim 1, wherein the second organic film further comprises at least one of a light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, and an electron injection layer.
13. A display device comprising the organic electroluminescent element as claimed in any one of claims 1 to 10.
14. A light source device comprising the organic electroluminescent element as claimed in any one of claims 1 to 10.
15. An electronic product comprising the organic electroluminescent device according to any one of claims 1 to 10.
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