CN116041334A - Blue light luminescent auxiliary material, preparation method thereof and organic electroluminescent device - Google Patents
Blue light luminescent auxiliary material, preparation method thereof and organic electroluminescent device Download PDFInfo
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- CN116041334A CN116041334A CN202310321953.7A CN202310321953A CN116041334A CN 116041334 A CN116041334 A CN 116041334A CN 202310321953 A CN202310321953 A CN 202310321953A CN 116041334 A CN116041334 A CN 116041334A
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- blue light
- auxiliary material
- light emitting
- independently selected
- compound
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- 238000002360 preparation method Methods 0.000 title abstract description 20
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D405/14—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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
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- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses a blue light luminescent auxiliary material, a preparation method thereof and an organic electroluminescent device, which belong to the technical field of organic light electroluminescent materials, wherein the structural general formula of the material is shown in the specification, and Ar is shown in the specification 1 ，Ar 2 Each independently selected from substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted 3-to 30-membered heteroaryl, ar 1 ，Ar 2 Adjacent substituents cannot be linked to each other to form a ring, and the heteroatoms in the heteroaryl groups are each independently selected from any one of oxygen, nitrogen or sulfur. The invention relates to an organic electroluminescent deviceThe light-emitting device has better comprehensive performance and obvious effect on prolonging the service life of the device. The method avoids the influence of poor stability of the material caused by molecular aggregation on the service life of a device, has better electron donating property with Shi Fang amine groups, is favorable for improving the hole mobility, and can avoid the obstruction of hole transmission caused by poor stacking property of the molecules due to over-torsion of the configuration.
Description
Technical Field
The invention belongs to the technical field of organic light-emitting materials, and particularly relates to a blue light-emitting auxiliary material, a preparation method thereof and an organic light-emitting device.
Background
Organic Light Emitting Diodes (OLEDs) have undergone many technological innovations, penetrating into various fields with advantages that are incomparable with conventional display and lighting technologies such as light weight, low energy consumption, high efficiency, softness, no glare, flexibility, and become a new star in the lighting and display fields.
The OLED presents multilayer as "sandwich type structural feature, specifically includes electrode material rete and presss from both sides the organic functional material between different electrode retes, includes: a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an emission layer (EML), an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL). In the current research, in order to reduce the potential barrier between the HTL and the EML and reduce the driving voltage of the OLED, a light-emitting auxiliary layer is generally disposed between the HTL and the EML to increase the utilization rate of holes, thereby improving the light-emitting efficiency, stability and lifetime of the OLED.
In recent years, research on materials of light-emitting auxiliary layers has been carried out, but materials with excellent device performance have been found, so that there is still a great development space for research on OLED light-emitting auxiliary materials. Finding luminescent auxiliary materials that are developed to match current or future OLED technologies is a matter of urgent need for those skilled in the art.
Disclosure of Invention
In view of the above, the invention provides a blue light emitting auxiliary material, a preparation method thereof and an organic electroluminescent device.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
the structural general formula of the blue light luminescent auxiliary material is shown as formula I:
wherein Ar is 1 ，Ar 2 Each independently selected from a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted 3-to 30-membered heteroaryl group, ar as described above 1 ，Ar 2 Adjacent substituents cannot be linked to each other to form a ring, and each heteroatom in the heteroaryl is independently selected from any one of oxygen, nitrogen, or sulfur.
Further, ar is as described above 1 ，Ar 2 Each independently selected from substituted or unsubstituted C6-C18 aryl, or substituted or unsubstituted 3-to 24-membered heteroaryl.
Further, ar is as described above 1 ，Ar 2 Each independently selected from phenyl, methylphenyl, m-dimethylphenyl, ethylphenyl, t-butylphenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, indenyl, triphenylenyl, pyrenyl, perylenyl, chrysene -yl, naphthaceneyl, fluoranthryl, spirobifluorenyl, azulenyl, methoxyphenyl, or cyanophenyl.
Further, ar is as described above 1 ，Ar 2 Each independently selected from furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, and combinations thereof,Bipyridyl, pyrazinyl, pyridazinyl, benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, azabiphenyl, benzodioxolyl, or dihydroacridinyl.
Further, ar is as described above 1 ，Ar 2 Each independently selected from phenyl, naphthyl, anthryl, phenanthryl, methylphenyl, m-dimethylphenyl, ethylphenyl, t-butylphenyl, cyanophenyl, methoxyphenyl, phenylpyridyl, biphenyl, terphenyl, phenylnaphthyl, dibenzofuranyl, dibenzothienyl, carbazolyl, 9-phenyl-9H-carbazolyl, diphenylfluorenyl, dimethylfluorenyl, or azabiphenyl;
the structural general formula I comprises a structure shown in a formula I-1-formula I-3:
in the above technical scheme, the substitution positions are defined as follows:
the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound becomes an additional substituent, and the position of substitution is not limited as long as the position is a position where the hydrogen atom is substituted, i.e., a position where the substituent can be substituted, and when two or more substituents are substituted, two or more substituents may be the same or different from each other.
The terms "substituted or unsubstituted C6-C30 aryl", "substituted or unsubstituted 3-to 30-membered heteroaryl", "substituted or unsubstituted C6-C18 aryl", "substituted or unsubstituted 3-to 24-membered heteroaryl", the number of carbon atoms in the aryl or heteroaryl representing the number of carbon atoms making up the unsubstituted aryl or the total number of heteroatoms and carbon atoms making up the heteroaryl, irrespective of the number of carbon atoms in the substituent.
The term "substituted or unsubstituted" means substituted with one, two or more substituents selected from the group consisting of: deuterium, halogen, nitrile, isocyano, hydroxy, mercapto, carbonyl, carboxylic acid, acyl, ester, silyl, boron, C1-C30 alkyl, C3-C30 cycloalkyl, C1-C30 heteroalkyl, C1-C30 arylalkyl, alkoxy, C6-C30 aryl, or 3-to 30-membered heteroaryl, or a substituent linked with two or more of the substituents shown above, or is unsubstituted.
Cycloalkyl means monocyclic, polycyclic or spiroalkyl;
aryl refers to a monocyclic aromatic hydrocarbon group or a polycyclic aromatic ring system, polycyclic having two or more rings in which two carbons are common to two adjoining rings (the rings described above being "fused");
heteroaryl groups include monocyclic aromatic groups and polycyclic aromatic ring systems of at least one heteroatom, including but not limited to O, S, N, P, B, si or Se.
Further, the blue light emitting auxiliary material is selected from any one of the compounds represented by the following structural formulas:
the invention also provides a preparation method of the blue light luminescent auxiliary material, which comprises the following steps:
(1) Under the protection of nitrogen, sequentially adding reactants A-I, reactants B-I, alkali, a palladium catalyst, toluene, ethanol and water into a reaction container, heating, refluxing, cooling to room temperature, adding water, filtering after solid precipitation is finished, 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;
(2) Under the protection of nitrogen, after the intermediate C-I and the reactant D-I are completely dissolved in dimethylbenzene in a reaction container, adding alkali, a palladium catalyst and a phosphine ligand into the reaction container, heating and stirring the obtained product, carrying out suction filtration by using kieselguhr while the obtained product is hot, cooling filtrate to room temperature, adding water into the filtrate for washing, separating liquid, retaining an organic phase, extracting an aqueous phase by using ethyl acetate, drying the combined organic layer by using magnesium sulfate, and purifying the residual substance by using column chromatography to obtain the compound shown as the formula-I;
the synthetic route is as follows:
wherein,,
hal is each independently selected from Br or I;
r' is
Or->
。
Further, in the step (1), the molar ratio of the reactants A-I, B-I, the alkali and the palladium catalyst is 1.0 (1.0-1.2): 2.0-2.3): 0.01-0.02.
Further, in the step (2), the molar ratio of the intermediate C-I, the reactant D-I, the base, the palladium catalyst and the phosphine ligand is 1.0 (1.1-1.3): 2.0-2.4): 0.01-0.05): 0.02-0.15.
Further, the palladium catalyst is Pd 2 (dba) 3 、Pd(PPh 3 ) 4 、PdCl 2 、PdCl 2 (dppf)、Pd(OAc) 2 、Pd(PPh 3 ) 2 Cl 2 Or NiCl 2 (dppf) one or a mixture of several kinds.
Further, the phosphine ligand is P (t-Bu) 3 、X-phos、PET 3 、PMe 3 、PPh 3 、KPPh 2 Or P (t-Bu) 2 One or a mixture of several of Cl.
Further, the above base is K 2 CO 3 、K 3 PO 4 、Na 2 CO 3 、CsF、Cs 2 CO 3 Or one or a mixture of several of t-Buona.
In the step (1), the volume ratio of toluene, ethanol and water is (2-4): 1:1.
Further, in the step (1), the temperature is raised to 80-100 ℃ and the mixture is refluxed for 8-12 hours.
Further, in the step (2), the above is heated to 130-140℃and stirred for 8-12 hours.
The invention also provides an organic electroluminescent device, which comprises the blue light luminescent auxiliary material or the blue light luminescent auxiliary material prepared by the method.
The invention has the beneficial effects that: the invention provides a blue light luminescent auxiliary material containing aromatic amine of dibenzofuran, wherein 9-phenyl-9H-carbazole is connected at the 2 position of the dibenzofuran, and the aromatic amine is bonded to the 4 position of the dibenzofuran. The organic electroluminescent device prepared from the blue light luminescent auxiliary material provided by the invention has good comprehensive performance, and particularly has obvious effect of improving the service life of the device.
According to the invention, the space configuration of the compound is regulated by bonding aromatic amine to the 4-position of dibenzofuran, so that the influence of poor stability of the material caused by molecular aggregation on the service life of a device is avoided, and the Shi Fang amine group has better electron donating property, thereby being beneficial to improving the hole mobility; the 9-phenyl-9H-carbazole is connected at the 2 position of the dibenzofuran to improve the configuration torsion, and meanwhile, the buffer between the carbazolyl and the dibenzofuran through the phenylene can avoid poor molecular stacking property to prevent hole transport due to the excessive configuration torsion.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of intermediate C-8 in example 1.
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of compound 8 in example 1.
Detailed Description
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The reactant B-I has two halogens, the reaction site is controlled by controlling the reaction condition according to the characteristic that the reactivity I > Br > Cl in the palladium catalytic coupling reaction to prepare an intermediate, and the intermediate is purified by using a column chromatography or a silica gel funnel to react, so that byproducts are removed, and the target compound is obtained. 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 8
Under nitrogen, reactant A-8 (50 mmol, CAS: 864977-33-3), reactant B-8 (60 mmol, CAS: 2409784-63-8), potassium carbonate (110 mmol), tetrakis (triphenylphosphine) palladium (0.5 mmol), toluene, ethanol and water (V) were added sequentially to a round bottom flask Toluene (toluene) ：V Ethanol :V Water and its preparation method =150 ml:50 ml), heating to 95 ℃, refluxing for 10 hours, cooling to room temperature, adding water, filtering after the solid is precipitated, drying a filter cake, purifying the residual substance by column chromatography, removing the solvent from the filtrate by a rotary evaporator, and drying the obtained solid to obtain an intermediate C-8. (15.76 g, yield: 71%, test value MS (ESI, M/Z): [ M+H ]] + = 444.08）。
The nuclear magnetic resonance hydrogen spectrum of intermediate C-8 is shown in FIG. 1.
Intermediate C-8 (40 mmol) and reactant D-8 (45 mmol, CAS:32228-99-2) were combined in a round bottom flask under nitrogen) After complete dissolution in xylene (200 mL), sodium t-butoxide (80 mmol), bis (tri-t-butylphosphine) palladium (0.4 mmol), tri-t-butylphosphine (0.8 mmol) were added thereto, and the resultant was heated to 135 ℃ and stirred for 10 hours. Filtering with diatomaceous earth while hot, cooling the filtrate to room temperature, adding water into the filtrate, washing, separating to obtain organic phase, and extracting water phase with ethyl acetate; the combined organic layers were then dried over magnesium sulfate and the remaining material was purified by column chromatography to give compound 8. (19.06 g, yield: 73%, test value MS (ESI, M/Z): [ M+H ]] + = 653.01）。
The nuclear magnetic resonance hydrogen spectrum of compound 8 is shown in fig. 2.
Characterization:
HPLC purity: > 99.8%.
Elemental analysis:
theoretical value: c, 88.32, H, 4.94, N, 4.29, O, 2.45
Test value: c, 88.29, H, 5.01, N, 4.31, O, 2.47
Example 2: synthesis of Compound 148
Under nitrogen, reactant A-148 (50 mmol, CAS: 1189047-28-6), reactant B-8 (60 mmol), potassium carbonate (110 mmol), tetrakis (triphenylphosphine) palladium (0.5 mmol), toluene, ethanol and water (V) were added sequentially to a round bottom flask Toluene (toluene) ：V Ethanol :V Water and its preparation method =150 ml:50 ml), heating to 95 ℃, refluxing for 10 hours, cooling to room temperature, adding water, filtering after the solid is precipitated, drying a filter cake, purifying the residual substance by column chromatography, removing the solvent from the filtrate by a rotary evaporator, and drying the obtained solid to obtain an intermediate C-148. (16.20 g, yield: 73%, test value MS (ESI, M/Z): [ M+H ]] + = 444.07）。
Intermediate C-148 (40 mmol) and reactant D-148 (45 mmol, CAS: 1592943-27-5) were completely dissolved in xylene in a round bottom flask under nitrogen protectionAfter (200 mL), sodium t-butoxide (80 mmol), bis (tri-t-butylphosphine) palladium (0.4 mmol), tri-t-butylphosphine (0.8 mmol) were added thereto, and then the resultant was heated to 135℃and stirred for 10 hours. Filtering with diatomaceous earth while hot, cooling the filtrate to room temperature, adding water into the filtrate, washing, separating to obtain organic phase, and extracting water phase with ethyl acetate; the combined organic layers were then dried over magnesium sulfate and the remaining material was purified by column chromatography to afford compound 148. (22.33 g, yield: 69%, test value MS (ESI, M/Z): [ M+H ]] + = 809.28）。
Characterization:
HPLC purity: > 99.8%.
Elemental analysis:
theoretical value: c, 89.08, H, 5.48, N, 3.46, O, 1.98
Test value: c, 88.77, H, 5.55, N, 3.50, O, 2.23
Example 3: synthesis of Compound 256
After intermediate C-256 (40 mmol) and reactant D-256 (45 mmol, CAS: 1318338-47-4) were completely dissolved in xylene (200 mL) in a round bottom flask under nitrogen protection, sodium t-butoxide (80 mmol), bis (tri-t-butylphosphine) palladium (0.4 mmol), tri-t-butylphosphine (0.8 mmol) were added thereto, and then the mixture was stirredThe resultant was heated to 135℃and stirred for 10 hours. Filtering with diatomaceous earth while hot, cooling the filtrate to room temperature, adding water into the filtrate, washing, separating to obtain organic phase, and extracting water phase with ethyl acetate; the combined organic layers were then dried over magnesium sulfate and the remaining material was purified by column chromatography to give compound 256. (22.88 g, yield: 77%, test value MS (ESI, M/Z): [ M+H ]] + = 743.11）。
Characterization:
HPLC purity: > 99.8%.
Elemental analysis:
theoretical value: c, 87.31, H, 4.61, N, 3.77, O, 4.31
Test value: c, 87.23, H, 4.69, N, 3.79, O, 4.36
Examples 4 to 65
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 invention provides an organic electroluminescent device, which specifically comprises 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 and a capping layer which are used as organic layers. In one embodiment, the organic light emitting element is described as an "organic layer" disposed between the cathode and anode, which may be achieved by combining the above layers, or omitting or adding some layers entirely.
According to one embodiment of the present specification, the compound of formula I prepared according to the present invention is used as a light-emitting auxiliary layer material.
The anode is made of a conductor, such as a metal, metal oxide, and/or conductive polymer, having a higher work function to aid in hole injection. The metal is selected from nickel, platinum, vanadium, chromium, copper, zinc, gold, silver or alloys thereof; the metal oxide is selected from zinc oxide, indium Tin Oxide (ITO) and indium zinc oxide; the combination of metal and oxide is ZnO and A1 or SnO 2 Sb or ITO and Ag; the conductive polymer is selected from poly (3-methylthiophene), poly (3, 4- (ethylene-1, 2-dioxy) thiophene), polypyrrole and polyaniline, but is not limited thereto.
The hole injection layer and the hole transport layer efficiently inject or transport holes from the anode between the electrodes to which an electric field has been applied, and preferably have high hole injection efficiency and efficiently transport the injected holes. Therefore, a substance having a small ionization potential, a large hole mobility, and excellent stability, and which is less likely to cause impurities that become traps during production and use, is selected. The hole injection layer is selected to be a p-doped hole injection layer; the hole transport material is selected from arylamine derivatives, conductive polymers, block copolymers having conjugated and non-conjugated portions at the same time, and the like.
A light-emitting auxiliary layer (multi-layer hole transporting layer) is interposed between the hole transporting layer and the light-emitting layer, and functions to smoothly move holes from the anode to the light-emitting layer and block electrons from the cathode.
The light-emitting layer is a compound that emits light by excitation by recombination of holes and electrons, and is selected to have a stable thin film shape and to exhibit high light-emitting efficiency in a solid state. The light emitting layer is a single layer or multiple layers and comprises a host material and a dopant material. The amounts of the host material and the dopant material to be used may be determined in accordance with the respective material characteristics. The doping method is realized by co-evaporation with the main material or simultaneous evaporation after mixing with the main material.
The electron transport layer and the electron injection layer efficiently transport or inject electrons from the anode and cathode between the electrodes to which an electric field has been applied. An impurity substance which has high electron affinity, high electron mobility, excellent stability and is not liable to generate traps is selected.
The anode is a substance capable of injecting electrons with good efficiency, and the same material as that of the anode is selected. If a low work function metal is chosen that facilitates efficient electron injection, it is often necessary to dope trace amounts of lithium, cesium or magnesium to avoid its instability in the atmosphere.
There are no particular restrictions on other layer materials in an OLED device, except that the light-emitting auxiliary layer disclosed herein comprises formula I.
The organic electroluminescent composition and the organic electroluminescent device according to the present invention are described in detail below with reference to specific examples.
Application example 1 preparation of organic electroluminescent device:
a. ITO anode: washing ITO (indium tin oxide) -Ag-ITO (indium tin oxide) glass substrate with the coating thickness of 150nm in distilled water for 2 times, washing with ultrasonic waves for 30min, washing with distilled water for 2 times repeatedly, washing with ultrasonic waves for 10min, baking with a vacuum oven at 220 ℃ for 2 hours after washing, and cooling after baking is finished, so that the glass substrate can be used. The substrate is used as an anode, a vapor deposition device process is performed by using a vapor deposition machine, and other functional layers are sequentially vapor deposited on the substrate.
b. HIL (hole injection layer): vacuum evaporation of hole injection layer materials HT and P-dopant at an evaporation rate of 1 Å/s, wherein the ratio of the evaporation rates of HT and P-dopant is 97:3, the thickness is 10nm.
c. HTL (hole transport layer): HT of 120nm was vacuum deposited as a hole transport layer on top of the hole injection layer at a deposition rate of 1.5 Å/s.
d. Prime (light-emitting auxiliary layer): the compound 8 of the present invention was vacuum-deposited as a light-emitting auxiliary layer on top of the hole transport layer at a deposition rate of 0.5 Å/s at 10nm.
e. EML (light emitting layer): then, on the above light-emitting auxiliary layer, a Host material (Host) and a Dopant material (Dopant) having a thickness of 25nm were vacuum-evaporated as light-emitting layers at an evaporation rate of 1 Å/s, wherein the ratio of the evaporation rates of Host and Dopant was 97:3.
f. HB (hole blocking layer): a hole blocking layer having a thickness of 5.0nm was vacuum deposited at a deposition rate of 0.5. 0.5 Å/s.
g. ETL (electron transport layer): ET and Liq with a thickness of 35nm were vacuum-evaporated as electron transport layers at an evaporation rate of 1 Å/s. Wherein the evaporation rate ratio of ET to Liq is 50:50.
h. EIL (electron injection layer): an electron injection layer was formed by vapor deposition of 1.0nm on a Yb film layer at a vapor deposition rate of 0.5. 0.5 Å/s.
i. And (3) cathode: and evaporating magnesium and silver at 18nm at an evaporation rate ratio of 1 Å/s, wherein the evaporation rate ratio is 1:9, so as to obtain the OLED device.
j. Light extraction layer: CPL with a thickness of 70nm was vacuum deposited as a light extraction layer on the cathode at a deposition rate of 1 Å/s.
k. And packaging the substrate subjected to evaporation. Firstly, a gluing device is adopted to carry out a coating process on a cleaned cover plate by UV glue, then the coated cover plate is moved to a lamination working section, a substrate subjected to vapor deposition is placed at the upper end of the cover plate, and finally the substrate and the cover plate are bonded under the action of a bonding device, and meanwhile, the UV glue is cured by illumination.
The device structure is as follows:
ITO/Ag/ITO/HT P-dose (10 nm)/HT (120 nm)/prime (10 nm)/Host: dose (25 nm)/HB (5 nm)/ET: liq (35 nm)/Yb (1 nm)/Mg: ag (18 nm)/CPL (70 nm). The structural formula of the compound in the device is as follows:
application examples 2 to 65
The organic electroluminescent devices of application examples 2 to 65 were prepared according to the above-described preparation method of the organic electroluminescent device, except that compound 8 of application example 1 was replaced with the corresponding compound of examples 2 to 65, 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 8 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 8 in 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 8 in 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 8 in 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 8 in 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 8 in 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 8 in 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 8 in application example 1 was replaced with comparative compound 8, wherein the structural formula of comparative compound 8 is as follows:
comparative example 9
An organic electroluminescent device was prepared according to the above-described preparation method of an organic electroluminescent device, except that compound 8 in application example 1 was replaced with comparative compound 9, wherein the structural formula of comparative compound 9 is as follows:
the organic electroluminescent devices obtained in the above device examples 1 to 65 and device comparative examples 1 to 9 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)
Note that: bi=light emission efficiency/CIEy in table 2, the light emission efficiency is affected by chromaticity in the blue OLED device.
As can be seen from table 2, compared with the existing organic electroluminescent devices provided in comparative examples 1 to 9, the OLED device application examples 1 to 65 prepared by using the blue light emitting auxiliary material provided in the embodiment of the present invention exhibited significant advantages in terms of device lifetime, and compared with the comparative examples, the light emitting auxiliary material provided in the embodiment of the present invention was improved by 52 to 119 hours, and meanwhile, the driving voltage and the light emitting efficiency of the device were also slightly improved.
Wherein, compound 8 in the examples of the present invention is different from comparative compound 1 and comparative compound 2 in the group of substituted arylamine dibenzofurans and the position of substitution in the dibenzofurans. Compared with the comparative compound 1, the compound 8 and carbazole are buffered through phenylene, so that HOMO and LUMO energy levels can be effectively regulated, and the localization of carrier migration is avoided, so that the driving voltage and the luminous efficiency are improved; the 2-position of the dibenzofuran is substituted by the 9-phenyl-9H-carbazolyl in the compound 8, so that the torsion of the configuration of the compound is reduced relative to that of the comparison compound 1, the compound configuration can still be ensured to have certain torsion, the poor hole transfer property caused by poor intermolecular stacking property due to overlarge configuration torsion can be avoided, and the effect of reducing intermolecular acting force can be achieved, so that the service life of the obtained device is prolonged. As can be seen from table 2, the lifetime of compound 8 was improved by 95h compared to comparative compound 1. Compared with the comparative compound 2, the compound 8 has the advantages that the substituted arylamine dibenzofuran group in the comparative compound 2 is 2-dibenzofuranyl, so that the side configuration tends to be planar, intermolecular stacking is easy to generate, the thermal stability of the material is poor, the service life of the device is not favored, and the luminous efficiency of the compound 8 is basically equal to that of the comparative compound 2, the service life is improved by 0.2cd/A, the service life is improved by 86h, and the driving voltage is reduced by 0.36V as shown in the table 2.
In the embodiment of the invention, the compound 11 is compared with the comparative compound 3, and the difference is that the 1-naphthylamine phenyl and 9-phenyl-9H-carbazolyl are in different forms of substitution on dibenzofuran, the 1-naphthylamine phenyl and 9-phenyl-9H-carbazolyl in the comparative compound 3 are respectively substituted on isobenzofuran benzene rings, and are both substituted at meta positions with smaller positions relative to O ortho positions, so that the molecular configuration plane is overlarge, the film forming property is poor, and the service life of the device is poor.
In the embodiment of the invention, compared with the comparative compound 4, the compound 28 has the same group for substituting dibenzofuran, and the 9-phenyl-9H-carbazolyl and the di (4-biphenyl) amino are in meta-position on the dibenzofuran, but the compound 28 is favorable for stabilizing molecules compared with the comparative compound 4, so that the service life of the device is prolonged on the technical level that the luminous efficiency and the driving voltage are basically kept the same; compared with the comparative compound 5, the compound 28 is respectively carbazole and di (4-biphenyl) amino bridged on dibenzofuran through phenylene, has better space torsion capability compared with the compound 28 of the latter, is beneficial to prolonging the service life of the device, can be improved for 69 hours as shown in the table 2, and in addition, the triplet state energy (2.69 eV) of the compound 28 is higher than that of the comparative compound 5 (2.63 eV) through theoretical calculation, so that the energy loss of a luminescent layer is more favorably blocked, and the luminescent efficiency of the device is improved; in the comparative compound 6, the 3-position of the 9-phenyl-9H-carbazolyl is directly bonded with dibenzothiophene, which is unfavorable for configuration torsion, so that the service life of the device is poor and is less than that of the compound 28 of the invention by 99 hours; compared with the mode of buffering through benzene rings, the linkage between carbazole and dibenzofuran in the comparative compound 7 is not beneficial to the adjustment of HOMO and LUMO energy levels of the compound, and further influences the luminous efficiency of the device.
Comparing compound 92 with comparative compound 8 in the examples of the present invention, it can be seen that the two are distinguished from similar compound 28 and comparative compound 5, and that the former compound 92 has good space torsion ability, which is advantageous for improving the lifetime of the device.
In the embodiment of the invention, compared with the comparative compound 9, the compound 212 is directly bonded with dibenzofuran at the 2-position of 9-phenyl-9H-carbazolyl in the comparative compound 9, which is unfavorable for configuration torsion; the benzene ring attached in the 9-phenyl-9H-carbazolyl group makes the stability of comparative compound 9 poor, resulting in a reduction in device lifetime.
In conclusion, the blue light luminescent auxiliary material provided by the invention has obvious advantages in the aspect of the service life of the device due to the proper substitution position selection of the aromatic amine group and the 9-phenyl-9H-carbazole on the dibenzofuran, and simultaneously improves the aspects of the driving voltage and the luminous efficiency of the device.
It is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. While still being apparent from variations or modifications that may be made by those skilled in the art are within the scope of the invention.
Claims (10)
1. The blue light luminescent auxiliary material is characterized by having a structural general formula shown in formula I:
wherein Ar is 1 ，Ar 2 Each independently selected from a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted 3-to 30-membered heteroaryl group, said Ar 1 ，Ar 2 Adjacent substituents cannot be linked to each other to form a ring, and the heteroatoms in the heteroaryl groups are each independently selected from any one of oxygen, nitrogen or sulfur.
2. A blue light emitting auxiliary material according to claim 1, wherein said Ar 1 ，Ar 2 Each independently selected from substituted or unsubstituted C6-C18 aryl, or substituted or unsubstituted 3-membered to 24-memberedHeteroaryl groups of the members.
3. A blue light emitting auxiliary material according to claim 2, wherein said Ar 1 ，Ar 2 Each independently selected from phenyl, methylphenyl, m-dimethylphenyl, ethylphenyl, t-butylphenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, indenyl, triphenylenyl, pyrenyl, perylenyl, chrysene -yl, naphthaceneyl, fluoranthryl, spirobifluorenyl, azulenyl, methoxyphenyl, or cyanophenyl.
4. A blue light emitting auxiliary material according to claim 2, wherein said Ar 1 ，Ar 2 Each independently selected from the group consisting of furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, bipyridyl, pyrazinyl, pyridazinyl, benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, benzindolyl, benzidinyl, indazolyl, benzothiadiazolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, azabiphenyl, benzodioxolyl, or dihydroacridinyl.
5. A blue light emitting auxiliary material according to claim 1, wherein said Ar 1 ，Ar 2 Each independently selected from phenyl, naphthyl, anthryl, phenanthryl, methylphenyl, m-dimethylphenyl, ethylphenyl, t-butylphenyl, cyanophenyl, methoxyphenyl, phenylPyridyl, biphenyl, terphenyl, phenylnaphthyl, dibenzofuranyl, dibenzothienyl, carbazolyl, 9-phenyl-9H-carbazolyl, diphenylfluorenyl, dimethylfluorenyl or azabiphenyl;
the structural general formula I comprises a structure shown in a formula I-1-formula I-3:
6. a blue light emitting auxiliary material according to claim 1, wherein said blue light emitting auxiliary material is selected from any one of the compounds represented by the following structural formulas:
7. a method for preparing the blue light emitting auxiliary material according to any one of claims 1 to 6, comprising the steps of:
(1) Under the protection of nitrogen, sequentially adding reactants A-I, reactants B-I, alkali, a palladium catalyst, toluene, ethanol and water into a reaction container, heating, refluxing, cooling to room temperature, adding water, filtering after solid precipitation is finished, 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;
(2) Under the protection of nitrogen, after the intermediate C-I and the reactant D-I are completely dissolved in dimethylbenzene in a reaction container, adding alkali, a palladium catalyst and a phosphine ligand into the reaction container, heating and stirring the obtained product, carrying out suction filtration by using kieselguhr while the obtained product is hot, cooling filtrate to room temperature, adding water into the filtrate for washing, separating liquid, retaining an organic phase, extracting an aqueous phase by using ethyl acetate, drying the combined organic layer by using magnesium sulfate, and purifying the residual substance by using column chromatography to obtain the compound shown as the formula-I;
the synthetic route is as follows:
wherein,,
hal is each independently selected from Br or I;
r' is
Or->
。
8. The method of preparing a blue light emitting phosphor according to claim 7, wherein in the step (1), the molar ratio of the reactant A-I, the reactant B-I, the base and the palladium catalyst is 1.0 (1.0-1.2): 2.0-2.3): 0.01-0.02.
9. The method of preparing a blue light emitting phosphor according to claim 7, wherein in the step (2), the molar ratio of the intermediate C-I, the reactant D-I, the base, the palladium catalyst and the phosphine ligand is 1.0 (1.1-1.3): 2.0-2.4): 0.01-0.05): 0.02-0.15.
10. An organic electroluminescent device comprising the blue light emitting auxiliary material according to any one of claims 1 to 6 or the blue light emitting auxiliary material prepared by the method according to any one of claims 7 to 9.
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