CN116253723A - Blue light luminescent auxiliary material and preparation method and application thereof - Google Patents
Blue light luminescent auxiliary material and preparation method and application thereof Download PDFInfo
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- CN116253723A CN116253723A CN202310222223.1A CN202310222223A CN116253723A CN 116253723 A CN116253723 A CN 116253723A CN 202310222223 A CN202310222223 A CN 202310222223A CN 116253723 A CN116253723 A CN 116253723A
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- blue light
- auxiliary material
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Images
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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Abstract
The invention discloses a blue light luminescent auxiliary material, a preparation method and application thereof, and relates to the field of organic photoelectric materials, wherein the molecular structural general formula of the blue light luminescent auxiliary material is represented by formula I:
wherein in the formula I, ar 1 ，Ar 2 Independently selected from substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted 3-to 30-membered heteroaryl. The luminescent auxiliary material provided by the embodiment of the invention is prepared fromThe organic electroluminescent device exhibits a long lifetime, improved luminous efficiency, and performance advantages of a driving voltage.
Description
Technical Field
The invention relates to the field of organic photoelectric materials, in particular to a luminescent auxiliary material and a preparation method and application thereof.
Background
Organic electroluminescence (OLED) is a type of self-luminous display element, and a display has advantages of high brightness, high resolution, wide viewing angle, low power consumption, and high response speed. In general, organic electroluminescence refers to a phenomenon in which an organic substance converts electric energy into light energy. An organic light emitting element utilizing an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer therebetween. Such as a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), a light emitting layer, an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL).
In order to solve the lifetime and efficiency problems, a light-emitting auxiliary layer (multi-layer hole transport layer) is generally added between the hole transport layer and the light-emitting layer. The light-emitting auxiliary layer mainly functions as an auxiliary hole transport layer, and is therefore sometimes also referred to as a second hole transport layer. The light-emitting auxiliary layer can enable holes transferred from the anode to smoothly move to the light-emitting layer, and can block electrons transferred from the cathode so as to limit the electrons in the light-emitting layer, reduce potential barriers between the hole-transporting layer and the light-emitting layer, reduce driving voltage of the organic electroluminescent device, further increase utilization rate of the holes, and improve luminous efficiency and service life of the device.
But there are few materials that can form a light emitting auxiliary layer and have excellent device performance. In particular, the service life and luminous efficiency of the OLED are not obviously improved, so it is important to develop higher-performance organic functional materials to meet the requirements of panel manufacturing enterprises.
Therefore, providing a blue light emitting auxiliary material with excellent device performance is a problem that needs to be solved by those skilled in the art.
Disclosure of Invention
In order to achieve the above purpose, the present invention adopts the following technical scheme: the blue light luminescent auxiliary material provided by the invention is based on benzo [ b ] naphtho [2,1-d ] furan, 9-phenyl-9H-carbazole is connected to naphthalene, and triarylamine groups are connected with benzene rings on the other side. The organic electroluminescent device prepared from the luminescent auxiliary material provided by the embodiment of the invention has the performance advantages of long service life, improved luminous efficiency and driving voltage.
A blue light luminescent auxiliary material has a molecular structural general formula represented by formula I:
wherein in the formula I, ar 1 ，Ar 2 Independently selected from substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl;
preferably, the Ar 1 ，Ar 2 Independently selected from substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted 3-to 24-membered heteroaryl.
Preferably, the Ar 1 ，Ar 2 Selected from cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 3-methylcyclopentyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, 2, 3-dimethylcyclopentyl, bicyclo [3.1.1 ]]Heptyl and adamantyl.
Preferably, the Ar 1 ，Ar 2 Selected from phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, and benzeneA naphthylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, indenyl, triphenylenyl, pyrenyl, perylenyl, droyl, naphtoneyl, fluoranthryl, spirobifluorenyl, azulenyl, methylphenyl, ethylphenyl, methoxyphenyl, and cyanophenyl group.
Preferably, the Ar 1 ，Ar 2 Selected from the group consisting of furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, and dihydroacridinyl.
Preferably, the Ar 1 ，Ar 2 Each independently selected from phenyl, naphthyl, phenanthryl, methylphenyl, ethylphenyl, cyanophenyl, methoxyphenyl, phenylpyridyl, phenylpyrimidinyl, biphenyl, terphenyl, phenylnaphthyl, dibenzofuranyl, dibenzothienyl, carbazolyl, 9-phenyl-9H-carbazolyl, diphenylfluorenyl, dimethylfluorenyl, cyclopentyl, cyclohexyl.
Preferably, the formula I is represented by the structure shown below:
preferably, the substituted or unsubstituted means substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a nitrile group; a hydroxyl group; a carbonyl group; an ester group; a silyl group; a boron base; C1-C30 alkyl; cycloalkyl of C3-C30; an alkoxy group; aryl of C6-C30; heteroaryl groups of 3-to 30-membered, or substituted with a substituent to which two or more substituents of the substituents shown above are attached, or not have a substituent.
Preferably, cycloalkyl refers to monocyclic, polycyclic and spiroalkyl groups.
Preferably, the aryl group refers to monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems, and the polycyclic ring may have two or more rings in which two carbons are common to two adjoining rings (the rings being "fused").
Preferably, the heteroaryl group includes a monocyclic aromatic group and a polycyclic aromatic ring system of at least one heteroatom including, but not limited to O, S, N, P, B, si and Se.
Preferably, the formula I includes the following structure:
a preparation method of a blue light luminescent auxiliary material comprises the following synthetic routes of the intermediate:
wherein Hal is selected from Br, I; r' is
Ar 1 -Ar 2 The same as the above range;
N 2 under the protection, adding reactants A-I (1.0 eq), reactants B-I (1-1.2 eq), palladium catalyst (0.01-0.02 eq) and phosphorus ligand (0.02-0.05 eq) and alkali (2.0-2.3 eq) into a mixed solvent of toluene, ethanol and water (2-4:1:1) respectively, heating to 80-100 ℃, reacting for 8-12H, cooling to room temperature, and adding H 2 Filtering after the solid is separated out, drying a filter cake, purifying the residual substances by using a column chromatography, removing the solvent from the filtrate by using a rotary evaporator, and drying the obtained solid to obtain an intermediate C-I;
N 2 under the protection, after adding the intermediate C-I (1.0 eq) and the reactant D-I (1.1-1.3 eq) into a reaction vessel and dissolving in xylene, adding a palladium catalyst (0.01-0.05 eq), a phosphorus ligand (0.02-0.15 eq) and a base (2.0-2.4 eq); after the addition, the reaction temperature is slowly increased to 130-140 ℃, and the mixture is stirred for 8-12h; filtering with diatomaceous earth while hot, cooling the filtrate to room temperature, adding distilled water into the filtrate, washing, separating to obtain organic phase, and extracting water phase with ethyl acetate; the combined organic layers were then dried over magnesium sulfate and the remaining material was purified by column chromatography to give formula I.
The preparation method of the blue light luminescent auxiliary material comprises the following steps of: pd (Pd) 2 (dba) 3 ，Pd(PPh 3 ) 4 ，PdCl 2 ，PdCl 2 (dppf)，Pd(OAc) 2 ，Pd(PPh 3 ) 2 Cl 2 ，NiCl 2 One of (dppf); phosphine ligands include: p (t-Bu) 3 ，X-phos，PET 3 ，PMe 3 ，PPh 3 ，KPPh 2 ，P(t-Bu) 2 One of Cl; the base includes: k (K) 2 CO 3 ，K 3 PO 4 ，Na 2 CO 3 ，CsF，Cs 2 CO 3 One of t-BuONa.
Use of a blue light emitting auxiliary material in an organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer arranged between the first electrode and the second electrode, the organic layer comprising the blue light emitting auxiliary material according to any of the preceding claims.
Compared with the prior art, the invention has the following beneficial effects:
the blue light luminescent auxiliary material provided by the invention is based on benzo [ b ] naphtho [2,1-d ] furan, 9-phenyl-9H-carbazole is connected to naphthalene, and triarylamine groups are connected with benzene rings on the other side. The organic electroluminescent device prepared from the luminescent auxiliary material provided by the embodiment of the invention has the performance advantages of long service life, improved luminous efficiency and driving voltage.
9-phenyl-9H-carbazole is connected to naphthalene of benzo [ b ] naphtho [2,1-d ] furan, and the introduced phenyl bridging structure can avoid large electron jump difficulty caused by overlarge structural energy gap, and the compound has stable structure and can effectively prolong the service life of devices. Triarylamines have excellent hole transport properties, and typically the hole transport layer, the light emitting auxiliary layer, and the electron blocking layer have triarylamine groups. The triarylamine material is used as the light-emitting auxiliary layer, so that the mobility is improved.
Further research shows that not all the connecting and ring on dibenzofuran can reach the effect of high triplet state energy level, and the positions of the parallel rings and the substituents on the parallel rings among similar substances can influence the triplet state energy level and mobility, thereby influencing the device performance in the organic electroluminescence.
The conjugated surface of the compound formed by benzo [ b ] naphtho [2,3-d ] furan is increased, but the triplet energy level is greatly reduced. Thus benzo [ b ] naphtho [2,1-d ] furans are selected as parent nuclei for the present invention to give higher triplet energy levels to the compounds.
The benzo [ b ] naphtho [2,1-d ] furan adopted by the invention maintains the advantage of dibenzofuran high triplet state energy level, and on the basis, a conjugated surface is added, so that the hole transmission rate is increased, the efficiency is improved, the extension of the conjugated surface is avoided, and the higher triplet state energy level required by the blue light luminescent auxiliary material is ensured.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings that are required to be used in the embodiments or the description of the prior art will be briefly described below, and it is obvious that the drawings in the following description are only embodiments of the present invention, and that other drawings can be obtained according to the provided drawings without inventive effort for a person skilled in the art.
FIG. 1 is a graph showing the nuclear magnetic resonance hydrogen spectrum of intermediate C-170 of the present invention;
FIG. 2 is a graph showing the hydrogen nuclear magnetic resonance spectrum of the compound 170 of the present invention.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The invention carries out a series of palladium catalytic coupling reactions, on one hand, utilizes the difference that the activity of Br is larger than that of Cl, on the other hand, controls the reaction sites by controlling the reaction conditions, and uses column chromatography or silica gel funnel purification reaction to remove byproducts, thus obtaining the target compound. The following are referred to in the common general knowledge:
transition metal organic chemistry (original sixth edition), robert H-crabtree (Robert H.Crabtree), press: publication time of Shanghai Shandong university Press: 2017-09-00, ISBN:978-7-5628-5111-0, page 388.
Organic chemistry and photoelectric Material Experimental Instructions, chen Runfeng, press: university of east south Press, publication time: 2019-11-00, ISBN:9787564184230, page 174.
Example 1
Synthesis of Compound 1
CAS: reactant B-1:2612140-92-6
N 2 Under the protection, the reactant A-1 (50 mmol), the reactant B-1 (60 mmol), the tetrakis (triphenylphosphine) palladium (0.5 mmol) and the potassium carbonate (110 mmol) are respectively added into a mixed solvent of toluene, ethanol and water (150 mL:50 mL), the temperature is raised to 95 ℃, the reaction is carried out for 10 hours, the temperature is cooled to room temperature, and H is added 2 And O, filtering after the solid is precipitated, drying a filter cake, purifying the residual substances by using a column chromatography, removing the solvent from the filtrate by using a rotary evaporator, and drying the obtained solid to obtain an intermediate C-1.(18.78 g, yield: 76%, test value MS (ESI, M/Z): [ M+H ]]+＝494.29)。
N 2 After the intermediate C-1 (35 mmol) and the reactant D-1 (38.5 mmol) were dissolved in xylene (200 mL) and Pd (OAc) was added to the reaction vessel under protection 2 (0.7 mmol), X-Phos (1.4 mmol), t-BuONa (77 mmol); after the addition, the reaction temperature was slowly raised to 135 ℃ and the mixture was stirred for 10h; filtering with diatomaceous earth while hot, cooling the filtrate to room temperature, adding distilled water into the filtrate, washing, separating to obtain organic phase, and extracting water phase with ethyl acetate; the combined organic layers were then dried over magnesium sulfate and the remaining material was purified by column chromatography to give compound 1. (21.82 g, yield: 80%, test value MS (ESI, M/Z): [ M+H ]]+＝779.21)。
The yields in the above steps are the fractional yields of the corresponding steps.
Characterization:
HPLC purity: > 99.9%.
Elemental analysis:
theoretical value: c,89.43; h,4.92; n,3.60; o,2.05
Test value: c,89.13; h,5.06; n,3.71; o,2.17
Example 2: synthesis of Compound 91
CAS: reactant B-91:2411141-57-4
N 2 Under the protection, the reactant A-91 (50 mmol), the reactant B-91 (60 mmol), the tetrakis (triphenylphosphine) palladium (0.5 mmol) and the potassium carbonate (110 mmol) are respectively added into a mixed solvent of toluene, ethanol and water (150 mL:50 mL), the temperature is raised to 95 ℃, the reaction is carried out for 10 hours, the temperature is cooled to room temperature, and H is added 2 And O, filtering after the solid is precipitated, drying a filter cake, purifying the residual substances by using a column chromatography, removing the solvent from the filtrate by using a rotary evaporator, and drying the obtained solid to obtain an intermediate C-91. (17.79 g, yield: 72%, test value MS (ESI, M/Z): [ M+H ]]+＝494.23)。
N 2 After the intermediate C-91 (35 mmol) and the reactant D-91 (38.5 mmol) were added to the reaction vessel and dissolved in xylene (200 mL) under protection, pd (OAc) was added 2 (0.7 mmol), X-Phos (1.4 mmol), t-BuONa (77 mmol); after the addition, the reaction temperature was slowly raised to 135 ℃ and the mixture was stirred for 10h; filtering with diatomaceous earth while hot, cooling the filtrate to room temperature, adding distilled water into the filtrate, washing, separating to obtain organic phase, and extracting water phase with ethyl acetate; the combined organic layers were then dried over magnesium sulfate and the remaining material was purified by column chromatography to give compound 91. (22.75 g, yield: 78%, test value MS (ESI, M/Z): [ M+H ]]+＝833.32)。
The yields in the above steps are the fractional yields of the corresponding steps.
Characterization:
HPLC purity: > 99.8%.
Elemental analysis:
theoretical value: c,87.96; h,4.84; n,3.36; o,3.84
Test value: c,87.70; h,5.01; n,3.48; o,3.91
Example 3: synthesis of Compound 170
CAS: reactant B-170:2625815-01-0
N 2 Under the protection, the reactants A-170 (50 mmol), B-170 (60 mmol), tetra (triphenylphosphine) palladium (0.5 mmol) and potassium carbonate (110 mmol) are respectively added into a mixed solvent of toluene, ethanol and water (150 mL:50 mL), the temperature is raised to 95 ℃, the reaction is carried out for 10H, the temperature is cooled to room temperature, and H is added 2 And O, filtering after the solid is separated out, drying a filter cake, purifying the residual substances by using a column chromatography, removing the solvent from the filtrate by using a rotary evaporator, and drying the obtained solid to obtain an intermediate C-170. (18.29 g, yield: 74%, test value MS (ESI, M/Z): [ M+H ]]+＝494.32)。
The nuclear magnetic resonance hydrogen spectrum of intermediate C-170 is shown in FIG. 1.
N 2 After the addition of intermediate C-170 (35 mmol) and reactant D-170 (38.5 mmol) in xylene (200 mL) to the reaction vessel under protection, pd (OAc) was added 2 (0.7 mmol), X-Phos (1.4 mmol), t-BuONa (77 mmol); after the addition, the reaction temperature was slowly raised to 135 ℃ and the mixture was stirred for 10h; filtering with diatomaceous earth while hot, cooling the filtrate to room temperature, adding distilled water into the filtrate, washing, separating to obtain organic phase, and extracting water phase with ethyl acetate; the combined organic layers were then dried over magnesium sulfate and the remaining material was purified by column chromatography to give compound 170. (25.69 g, yield: 82%, test value MS (ESI, M/Z): [ M+H ]]+＝895.31)。
The nuclear magnetic resonance hydrogen spectrum of compound 170 is shown in fig. 2.
The yields in the above steps are the fractional yields of the corresponding steps.
Characterization:
HPLC purity: > 99.8%.
Elemental analysis:
theoretical value: c,89.90; h,5.18; n,3.13; o,1.79
Test value: c,89.78; h,5.31; n,3.18; o,1.85
Examples 4 to 58
The synthesis of the following compounds, whose molecular formulas and mass spectra are shown in table 1 below, was accomplished with reference to the synthesis methods of examples 1 to 3.
Table 1 molecular formula and mass spectrum
Further, since other compounds of the present invention can be obtained by referring to the synthetic methods of the above-described examples, they are not exemplified herein.
The present invention provides an organic electroluminescent device, which may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting auxiliary layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a capping layer, etc. as an organic layer. However, the structure of the organic light emitting element is not limited thereto, and may include a smaller or larger number of organic layers.
According to one embodiment of the present specification, the compound of formula I prepared according to the present invention is used as a light-emitting auxiliary layer material.
In the case of manufacturing the organic light-emitting device, the compound represented by the formula I may be formed by a vacuum vapor deposition method or a +solution coating method. The solution coating method is, but not limited to, spin coating, dip coating, blade coating, ink jet printing, screen printing, spray coating, roll coating, and the like.
The organic light emitting element of the present invention may be of a top emission type, a bottom emission type or a bi-directional emission type, depending on the materials used.
The device of the present invention may be used in organic light emitting devices including, but not limited to, flat panel displays, computer monitors, a medical monitor, a television, billboards, a light for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, a laser printer, a telephone, a cell phone, a tablet, a photo album, a Personal Digital Assistant (PDA), a wearable device, a notebook, a digital camera, a video camera, a viewfinder, a micro-display, a three-dimensional display, a virtual reality or augmented reality display, a vehicle, a video wall comprising a plurality of displays tiled together, theatre or venue screens, phototherapy devices, and signs.
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. As a specific example of the anode material that can be used in the present invention,metals such as vanadium, chromium, copper, zinc, gold and the like or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO A1 or SnO 2 A combination of metals such as Sb and the like and oxides; and conductive polymers such as polypyrrole and polyaniline.
The hole injection layer may employ a material that advantageously receives holes from the anode at low voltages, and the Highest Occupied Molecular Orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metalloporphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazabenzophenanthrene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, and polyaniline-based and polythiophene-based conductive polymer, etc., but are not limited thereto, and may further contain additional compounds capable of p-doping.
The hole transporting material is a material capable of receiving holes from the anode or the hole injecting layer and transporting the holes to the light emitting layer, and has high hole mobility. The hole transporting material may be selected from arylamine derivatives, conductive polymers, block copolymers having both conjugated and non-conjugated portions, and the like.
A light-emitting auxiliary layer (multilayer hole-transporting layer) is interposed between the hole-transporting layer and the light-emitting layer. The light-emitting auxiliary layer mainly functions as an auxiliary hole transport layer, and is therefore sometimes also referred to as a second hole transport layer. The light emitting auxiliary layer enables holes transferred from the anode to smoothly move to the light emitting layer, and can block electrons transferred from the cathode to confine electrons in the light emitting layer, reduce potential barrier between the hole transporting layer and the light emitting layer, reduce driving voltage of the organic electroluminescent device, further increase utilization ratio of holes, thereby improving luminous efficiency and lifetime of the device.
An electron blocking layer may be disposed between the hole transport layer and the light emitting layer. As the electron blocking layer, materials known in the art, such as an arylamine-based organic material, may be used.
The light-emitting substance of the light-emitting layer is a substance capable of receiving and binding holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, to emit light in the visible light region, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence.
The light emitting layer includes a host material and a dopant material.
The mass ratio of the host material to the doping material is 90-99.5:0.5-10.
The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, pyrimidine derivatives, and the like.
The dopant materials of the present invention include fluorescent doping and phosphorescent doping. May be selected from aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
The hole blocking layer may be disposed between the electron transport layer and the light emitting layer, and materials known in the art, such as triazine-based compounds, may be used.
The electron transport layer may function to facilitate electron transport. The electron transporting material is a material that advantageously receives electrons from the cathode and transports the electrons to the light emitting layer, preferably a material having high electron mobility. The electron transport layer may include an electron buffer layer, a hole blocking layer, an electron transport layer.
The electron injection layer may function to promote electron injection. Has an ability to transport electrons, and prevents excitons generated in the light emitting layer from migrating to the hole injection layer. The material of the electron injection layer includes, but is not limited to, metal such as oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylmethane, anthrone, their derivatives, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, ytterbium, or their alloys, metal complexes, nitrogen-containing 5-membered ring derivatives, and the like.
The cathode is generally preferably a material having a small work function so that electrons are smoothly injected into the organic material layerThe layer thickness of this layer is preferably between 0.5 and 5 nm. The cathode material is generally preferably a material having a small work function in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof: liF/A1 or LiO 2 And (3) multilayer structural materials such as (A1) and Mg/Ag.
In addition to the inclusion of formula I in the light emitting auxiliary layers disclosed herein, existing hole injection materials, hole transport auxiliary materials, dopant materials, hole blocking layer materials, electron transport layer materials, and electron injection materials may be used for other layer materials in an OLED device.
The organic electroluminescent composition and the organic electroluminescent device according to the present invention are described in detail below with reference to specific examples.
Application example 1 preparation of organic electroluminescent device:
a. ITO anode: washing an ITO (indium tin oxide) -Ag-ITO (indium tin oxide) glass substrate with the coating thickness of 150nm in distilled water for 2 times, washing by ultrasonic waves for 30min, repeatedly washing by distilled water for 2 times, washing by ultrasonic waves for 10min, transferring into a spin dryer for spin drying after washing, baking for 2 hours at 220 ℃ by a vacuum oven, and cooling after baking is finished, so that the glass substrate can be used. The substrate is used as an anode, a vapor deposition device process is performed by using a vapor deposition machine, and other functional layers are sequentially vapor deposited on the substrate.
b. HIL (hole injection layer): to be used for
The vacuum evaporation of the hole injection layer materials HT and P-dopant is performed, and the chemical formulas are shown below. The evaporation rate ratio of HT to P-dock is 97:3, the thickness is 10nm;
c. HTL (hole transport layer): to be used for
Vacuum evaporating 120nm HT as a hole transport layer on the hole injection layer;
d. prime (light-emitting auxiliary layer): to be used for
Vacuum evaporating 10nm of the compound of the present invention on the hole transport layer as a light-emitting auxiliary layer;
e. EML (light emitting layer): then on the light-emitting auxiliary layer to
The Host material (Host) and the Dopant material (Dopant) having a thickness of 25nm were vacuum-deposited as light-emitting layers, and the chemical formulas of Host and Dopant are shown below. Wherein the evaporation rate ratio of Host to Dopant is 97:3.
f. HB (hole blocking layer): to be used for
Is used for vacuum evaporation of a hole blocking layer with a thickness of 5.0 nm.
g. ETL (electron transport layer): to be used for
ET and Liq having a thickness of 35nm were vacuum-deposited as electron transport layers. Wherein the evaporation rate ratio of ET to Liq is 50:50.
h. EIL (electron injection layer): to be used for
The vapor deposition rate of Yb film layer was 1.0nm to form an electron injection layer.
i. And (3) cathode: to be used for
The vapor deposition rate ratio of magnesium and silver is 18nm, and the vapor deposition rate ratio is 1:9, so that the OLED device is obtained.
j. Light extraction layer: to be used for
Is vacuum on the cathodeCPL with a thickness of 70nm was vapor deposited as a light extraction layer.
k. And packaging the substrate subjected to evaporation. Firstly, a gluing device is adopted to carry out a coating process on a cleaned cover plate by UV glue, then the coated cover plate is moved to a lamination working section, a substrate subjected to vapor deposition is placed at the upper end of the cover plate, and finally the substrate and the cover plate are bonded under the action of a bonding device, and meanwhile, the UV glue is cured by illumination.
The device structure is as follows:
ITO/Ag/ITO/HT: P-pinch (10 nm, 3%)/HT (120 nm)/prime (formula I) (10 nm)/Host: pinch (25 nm, 3%)/HB (5 nm)/ET: liq (35 nm, 50%)/Yb (1 nm)/Mg: ag (18 nm, 1:9)/CPL (70 nm).
Application examples 2 to 58
The organic electroluminescent devices of application examples 2 to 58 were prepared according to the above-described preparation method of the organic electroluminescent device, except that compound 1 of application example 1 was replaced with the corresponding compound, respectively, to form a light-emitting auxiliary layer.
Comparative example 1
An organic electroluminescent device was prepared according to the above-described preparation method of an organic electroluminescent device, except that compound 1 in application example 1 was replaced with comparative compound 1, wherein the structural formula of comparative compound 1 is as follows:
comparative example 2
An organic electroluminescent device was prepared according to the above-described preparation method of an organic electroluminescent device, except that compound 1 of application example 1 was replaced with comparative compound 2, wherein the structural formula of comparative compound 2 is as follows:
comparative example 3
An organic electroluminescent device was prepared according to the above-described preparation method of an organic electroluminescent device, except that compound 1 of application example 1 was replaced with comparative compound 3, wherein the structural formula of comparative compound 3 is as follows:
comparative example 4
An organic electroluminescent device was prepared according to the above-described preparation method of an organic electroluminescent device, except that compound 1 of application example 1 was replaced with comparative compound 4, wherein the structural formula of comparative compound 4 is as follows:
comparative example 5
An organic electroluminescent device was prepared according to the above-described preparation method of an organic electroluminescent device, except that compound 1 of application example 1 was replaced with comparative compound 5, wherein the structural formula of comparative compound 5 is as follows:
comparative example 6
An organic electroluminescent device was prepared according to the above-described preparation method of an organic electroluminescent device, except that compound 1 of application example 1 was replaced with comparative compound 6, wherein the structural formula of comparative compound 6 is as follows:
comparative example 7
An organic electroluminescent device was prepared according to the above-described preparation method of an organic electroluminescent device, except that compound 1 of application example 1 was replaced with comparative compound 7, wherein the structural formula of comparative compound 7 is as follows:
comparative example 8
An organic electroluminescent device was prepared according to the above-described preparation method of an organic electroluminescent device, except that compound 1 of application example 1 was replaced with comparative compound 8, wherein the structural formula of comparative compound 8 is as follows:
the organic electroluminescent devices obtained in the above device examples 1 to 58 and device comparative examples 1 to 8 were characterized in terms of driving voltage, luminous efficiency, BI value and lifetime at a luminance of 1000 (nits), and the test results are shown in table 2 below:
TABLE 2 luminescence property test results (brightness value 1000 nits)
It is known to those skilled in the art that the energy level of the light-emitting auxiliary layer is matched with the light-emitting layer and the hole-transporting layer, and the target value to be adjusted is different for different light-emitting layers. The difference is larger for the light emitting layers of different colors. Even with the same blue light, there is a significant difference for different host, dopant materials. The blue light organic electroluminescent device is influenced by microcavity effect, and the luminous efficiency is greatly influenced by chromaticity, so that a BI value is introduced as the basis of the efficiency of the blue light luminescent material, and BI=luminous efficiency/CIEy. And the problems of short lifetime and low efficiency of blue light devices have been one of the problems that those skilled in the art are urgent to solve in the art.
As can be seen from table 2, the organic electroluminescent devices using the blue light emitting auxiliary materials provided in the examples of the present invention according to application examples 1 to 58 exhibited technical effects of improving driving voltage and lifetime while exhibiting an ultra-long device lifetime, compared to the conventional organic electroluminescent devices provided in comparative examples 1 to 8.
Compound 95 provided in the examples and comparative compound 2; compared with the comparative compound 5, the compound 70 is characterized in that 9-phenyl-9H-carbazole is connected to naphthalene of benzo [ b ] naphtho [2,1-d ] furan, and the introduced phenyl bridging structure can avoid great difficulty in electron jump caused by overlarge structural energy gap, has stable structure, can effectively prolong the service life of a device, increases the service life by about 70H, improves the service life by about 40 percent, and has greatly improved service life.
Wherein, compound 60 provided in the examples of the present invention and comparative compound 4; the present compound 129 was benzo [ b ] naphtho [1,2-d ] furan as compared to comparative compound 3, which was benzo [ b ] naphtho [2,3-d ] furan.
Through DFT (Density functional theory) calculation, the triplet energy in the ground state configuration is obtained through calculation by using Gaussian16 software, adopting a B3lyp functional group and 6-31g base group, optimizing the structure ground state configuration and using time-density functional theory (TDDFT). The triplet energy level of comparative compound 3 was 2.3138eV, that of compound 129 was 2.6329eV, and that of a compound comprising benzo [ b ] naphtho [2,3-d ] furan, although the conjugated surface was increased, the triplet energy level was significantly decreased.
The invention adopts benzo [ b ] naphtho [2,1-d ] furan, retains the advantage of dibenzofuran high triplet state energy level, increases conjugated surface on the basis, increases hole transmission rate, improves efficiency, avoids the extension of conjugated surface, ensures higher triplet state energy level required by blue light luminescent auxiliary material, has the technical effects of improving device efficiency, greatly prolonging service life and prolonging service life by nearly 80 hours
The invention further passes the device verification, the benzo [ b ] naphtho [1,2-d ] furan mother nucleus is changed into similar compound, such as comparative compound 6, which is benzo [ b ] naphtho [1,2-d ] thiophene, comparative compound 8 is dibenzofuran, example compound 12, and the service life of the device obtained by compound 73 is also obviously improved.
It can be seen that not all the rings attached to dibenzofuran can achieve the effect of high triplet energy level, and the positions of the rings and the substituents on the rings among similar substances affect the triplet energy level and mobility, thereby affecting the device performance in the organic electroluminescence. The structure of the compound is similar to that of the compound in the prior art, but the service life of the device can be remarkably prolonged only when the compound which accords with the formula I is used as a blue light luminescent auxiliary layer.
The blue light luminescent auxiliary material provided by the invention is based on benzo [ b ] naphtho [2,1-d ] furan, 9-phenyl-9H-carbazole is connected to naphthalene, and triarylamine groups are connected with benzene rings on the other side. The prepared organic electroluminescent device has the technical effects of high luminous efficiency, long service life and improvement of driving voltage.
The above description is only of the preferred embodiments of the present invention and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (10)
1. The blue light luminescent auxiliary material is characterized in that the molecular structural general formula is represented by formula I:
wherein in the formula I, ar 1 ，Ar 2 Independently selected from substituted or unsubstituted C3-C30 cycloalkyl groupsSubstituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl.
2. A blue light emitting auxiliary material according to claim 1, wherein said Ar 1 ，Ar 2 Independently selected from substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted 3-to 24-membered heteroaryl.
3. A blue light emitting auxiliary material according to claim 1, wherein said Ar 1 ，Ar 2 Selected from cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 3-methylcyclopentyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, 2, 3-dimethylcyclopentyl, bicyclo [3.1.1 ]]Heptyl, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, anthracenyl, indenyl, triphenylenyl, pyrenyl, perylenyl, droyl, naphtharenyl, fluoranthracenyl, spirobifluorenyl, azulenyl, methylphenyl, ethylphenyl, methoxyphenyl, cyanophenyl, furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl tetrazolyl, furazanyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxacyclic ringPentenyl and dihydroacridinyl.
4. A blue light emitting auxiliary material according to claim 1, wherein said Ar 1 ，Ar 2 Each independently selected from phenyl, naphthyl, phenanthryl, methylphenyl, ethylphenyl, cyanophenyl, methoxyphenyl, phenylpyridyl, phenylpyrimidinyl, biphenyl, terphenyl, phenylnaphthyl, dibenzofuranyl, dibenzothienyl, carbazolyl, 9-phenyl-9H-carbazolyl, diphenylfluorenyl, dimethylfluorenyl, cyclopentyl, cyclohexyl.
5. A blue light emitting auxiliary material according to claim 1, wherein said formula I is represented by the following structure:
6. blue light emitting auxiliary material according to any one of claims 1 to 5, characterized in that said substituted or unsubstituted means substituted by one or more substituents selected from the group consisting of: deuterium; a halogen group; a nitrile group; a hydroxyl group; a carbonyl group; an ester group; a silyl group; a boron base; C1-C30 alkyl; cycloalkyl of C3-C30; an alkoxy group; aryl of C6-C30; heteroaryl groups of 3-to 30-membered, or substituted with a substituent to which two or more substituents of the substituents shown above are attached, or not have a substituent.
7. A blue light emitting auxiliary material according to claim 1, wherein said formula I comprises the following structure:
8. a method for preparing a blue light emitting auxiliary material according to claim 1, wherein the synthetic route of the intermediate is as follows:
wherein Hal is selected from Br, I; r' is
Ar 1 -Ar 2 The same as the above range;
N 2 under the protection, adding reactants A-I (1.0 eq), reactants B-I (1-1.2 eq) and phosphorus ligand (0.02-0.05 eq) and alkali (2.0-2.3 eq) into a mixed solvent of toluene, ethanol and water (2-4:1:1), heating to 80-100 ℃, reacting for 8-12H, cooling to room temperature, and adding H 2 Filtering after the solid is separated out, drying a filter cake, purifying the residual substances by using a column chromatography, removing the solvent from the filtrate by using a rotary evaporator, and drying the obtained solid to obtain an intermediate C-I;
N 2 under the protection, after adding the intermediate C-I (1.0 eq) and the reactant D-I (1.1-1.3 eq) into a reaction vessel and dissolving in xylene, adding a palladium catalyst (0.01-0.05 eq), a phosphorus ligand (0.02-0.15 eq) and a base (2.0-2.4 eq); after the addition, the reaction temperature is slowly increased to 130-140 ℃, and the mixture is stirred for 8-12h; filtering with diatomaceous earth while hot, cooling the filtrate to room temperature, adding distilled water into the filtrate, washing, separating to obtain organic phase, and extracting water phase with ethyl acetate; the combined organic layers were then dried over magnesium sulfate and the remaining material was purified by column chromatography to give formula I.
9. A method of preparing the blue light emitting auxiliary material according to claim 1, wherein the palladium catalyst comprises: pd (Pd) 2 (dba) 3 ，Pd(PPh 3 ) 4 ，PdCl 2 ，PdCl 2 (dppf)，Pd(OAc) 2 ，Pd(PPh 3 ) 2 Cl 2 ，NiCl 2 One of (dppf); phosphine ligand packageThe method comprises the following steps: p (t-Bu) 3 ，X-phos，PET 3 ，PMe 3 ，PPh 3 ，KPPh 2 ，P(t-Bu) 2 One of Cl; the base includes: k (K) 2 CO 3 ，K 3 PO 4 ，Na 2 CO 3 ，CsF，Cs 2 CO 3 One of t-BuONa.
10. Use of a blue light emitting auxiliary material in an organic electroluminescent device, characterized in that the organic electroluminescent device comprises a first electrode, a second electrode, and an organic layer arranged between the first electrode and the second electrode, the organic layer comprising the blue light emitting auxiliary material according to any one of claims 1-7.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117003741A (en) * | 2023-10-08 | 2023-11-07 | 吉林奥来德光电材料股份有限公司 | Light-emitting auxiliary material, preparation method thereof, light-emitting device and light-emitting device |
| CN117229173A (en) * | 2023-11-16 | 2023-12-15 | 吉林奥来德光电材料股份有限公司 | Cover layer material, preparation method thereof and organic electroluminescent device comprising cover layer material |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104650029A (en) * | 2014-12-26 | 2015-05-27 | 北京鼎材科技有限公司 | Fused-heterocycle aromatic hydrocarbon derivative and application thereof |
| KR20200078156A (en) * | 2018-12-21 | 2020-07-01 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
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2023
- 2023-03-09 CN CN202310222223.1A patent/CN116253723A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104650029A (en) * | 2014-12-26 | 2015-05-27 | 北京鼎材科技有限公司 | Fused-heterocycle aromatic hydrocarbon derivative and application thereof |
| KR20200078156A (en) * | 2018-12-21 | 2020-07-01 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117003741A (en) * | 2023-10-08 | 2023-11-07 | 吉林奥来德光电材料股份有限公司 | Light-emitting auxiliary material, preparation method thereof, light-emitting device and light-emitting device |
| CN117003741B (en) * | 2023-10-08 | 2023-12-26 | 吉林奥来德光电材料股份有限公司 | Light-emitting auxiliary material, preparation method thereof, light-emitting device and light-emitting device |
| CN117229173A (en) * | 2023-11-16 | 2023-12-15 | 吉林奥来德光电材料股份有限公司 | Cover layer material, preparation method thereof and organic electroluminescent device comprising cover layer material |
| CN117229173B (en) * | 2023-11-16 | 2024-02-20 | 吉林奥来德光电材料股份有限公司 | Cover layer material, preparation method thereof and organic electroluminescent device comprising cover layer material |
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