CN112961187A - Organic luminescent metal iridium complex and application of organic electroluminescent device thereof - Google Patents
Organic luminescent metal iridium complex and application of organic electroluminescent device thereof Download PDFInfo
- Publication number
- CN112961187A CN112961187A CN202110158361.9A CN202110158361A CN112961187A CN 112961187 A CN112961187 A CN 112961187A CN 202110158361 A CN202110158361 A CN 202110158361A CN 112961187 A CN112961187 A CN 112961187A
- Authority
- CN
- China
- Prior art keywords
- light
- emitting
- luminescent
- complex
- organic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
Abstract
An organic luminescent metal iridium heterocomplex compound formed by pyridine or substituted pyridine and condensed aromatic heterocycle is combined with alkyl-fluoroalkyl mixed substituted phenylpyridine as an auxiliary ligand and a luminescent main ligand containing the condensed aromatic heterocycle to obtain a novel organic heterocomplex luminescent metal compound; the obtained organic luminescent metal complex can also have crosslinkable groups to obtain a solution film-forming organic luminescent layer and can be further crosslinked into an insoluble and infusible network structure. The disclosed organic luminescent metallic iridium complex applies to green or yellow OLED light emitting diodes with high efficiency and improved long lifetime.
Description
Technical Field
The invention relates to an organic light-emitting metal iridium complex and an organic electroluminescent device prepared from the same, which can be applied to an organic light-emitting OLED device, improve the solubility and sublimation evaporation processability of a light-emitting material, and improve the performance and large-scale production of an OLED display device.
Background
The organic semiconductor material belongs to a novel photoelectric material, and the large-scale research of the organic semiconductor material originates from the discovery of doped polyacetylene with the conductivity reaching the copper level by the white-skinned tree, A.Heeger and A.McDiamid in 1977. Subsequently, c.tang et al, Kodak corporation, 1987, invented small organic molecule light emitting diodes (OLEDs), r.friend and a.holmes, cambridge university, 1990, polymer light emitting diodes P-OLEDs, and s.forrest and m.thomson, 1998, invented higher efficiency phosphorescent organic light emitting diodes PHOLEDs. Since the organic semiconductor material has the advantages of easily adjustable structure, various obtainable varieties, adjustable energy band and low cost as the plastic film processing, and in addition, the organic semiconductor has many applications such as conductive film, electrostatic copying, photovoltaic solar cell application, organic thin film transistor logic circuit, organic light-emitting OLED panel display and illumination, etc., the Baichuan-Heeger-McDiamid three scientists have acquired Nobel prize in 2000.
As organic electroluminescent diodes for next-generation flat panel display applications, organic photoelectric semiconductor materials are required to have: 1. high luminous efficiency; 2. excellent electron and hole stability; 3. appropriate luminescent color and intense color scale; 4. excellent film forming processability. In principle, most conjugated organic molecules (including star emitters), conjugated polymers, and organic heavy metal complexes containing conjugated chromophore ligands have electroluminescent properties and are used in a variety of light emitting diodes, such as organic small molecule light emitting diodes (OLEDs), polymer organic light emitting diodes (polleds), and organic phosphorescent light emitting diodes (PHOLEDs). Phosphorescence PHOLED combines the light-emitting mechanisms of singlet excited state (fluorescence) and triplet excited state (phosphorescence), and is apparently much higher in light-emitting efficiency than small-molecule OLEDs and high-molecular POLED. Both the PHOLED fabrication technology and the excellent PHOLED materials are essential to achieve low power OLED display and illumination. The quantum efficiency and the luminous efficiency of the PHOLED are 3-4 times of those of the fluorescent OLED material, so that the generated heat is reduced, and the competitiveness of the OLED display panel is improved. This provides the possibility of making the OLED display or illumination as a whole beyond LCD displays and conventional light sources. Thus, existing high-end OLED devices are more or less doped with phosphorescent OLED materials.
The phosphorescent OLED material is characterized in that an organic luminescent group with certain conjugation is used as a bidentate chelate ligand, and forms a ring metal-ligand complex with metal elements such as iridium and platinum, under the condition of high-energy illumination (such as ultraviolet light excitation) or charge injection (electric excitation), the ring metal-ligand charge transfer (MLCT) becomes an exciton, and then returns to the ground state to cause luminescence. In the OLED device, charges are injected by injecting holes from the anode after a positive voltage is applied to the anode, injecting electrons after a negative voltage is applied to the cathode, passing through the electron transport layer and the hole transport layer, respectively, and simultaneously entering the bulk or host material of the emitting layer, the electrons finally entering the Lowest Unoccupied Molecular Orbital (LUMO) of the light emitting dopant, and the holes entering the Highest Occupied Molecular Orbital (HOMO) of the light emitting dopant to form excited light emitting dopant molecules (exciton state). The exciton state reverts to the ground state with the emission of light energy at a wavelength corresponding to the energy gap (HOMO-LUMO energy level difference) of the light emitting molecular dopant.
Many noble metal organic ligand complexes have been reported, which are affected by noble metals to enhance the spin-orbit effect, so that the phosphorescence which should be weak becomes strong and excellent phosphorescence emission is exhibited. The organic phosphorus light-emitting material improves the yield of the electroluminescent quantum by utilizing the triplet state, theoretically can reach 100 percent of internal quantum efficiency, and is proved to be a material which is widely applied to OLED luminescent devices. For example, a green-emitting tris (phenylpyridine) iridium (III) complex, abbreviated as Ir (PPY)3Having the structural formula:
the blue-emitting FirPic has the following structural formula:
the main ligand 4, 6-difluorophenylpyridine mainly gives out light.
The tri (octyl quinoline) iridium (III) complex compound capable of emitting red light has excellent high-efficiency emission performance (adv. Mater.19, 739(2007)), and the structural formula of the complex compound is as follows:
there are also many other classes of materials that are used in organic light emitting devices OLEDs, and corresponding documents are listed in table 1.
Table 1: various types of organic OLED semiconductor light-emitting materials have been reported:
however, most of the organometallic iridium complexes have sublimation and evaporation temperatures close to the decomposition temperature of the complexes due to the large molecular weight of the metal iridium tridentate complexes themselves and the large intermolecular forces between the conjugated light-emitting complexes. In addition, the defects that the organic metal iridium complex luminescent material is difficult to dissolve and purify and the like also influence the problem of large-scale production of OLED devices. In order to meet various requirements of continuous promotion of industrial production and obtain organic OLED display and illumination products with high efficiency and long service life, development of better and more efficient luminescent materials easy to manufacture is imperative. In addition, one of the future development trends is to use the organic metal luminescent material with good solubility to obtain a solution method through inkjet printing or other solution processing processes to manufacture the OLED organic luminescent device display screen or the lighting OLED device, and the solution is required to be filmed and become an infusible and insoluble luminescent layer through chemical crosslinking, thereby being beneficial to the preparation of the multilayer OLED luminescent device by using a full solution processing method in a lamination way.
One way of molecular design of organometallic iridium complex phosphorescent materials is to form an iridium complex with Ir using 3 identical chelating ligands containing N atoms. Another way is to use 1 or 2 chelating auxiliary ligands with shorter emission wavelength containing nitrogen or oxygen atoms to form a hybrid or heteroligand complex (hybrid or Heteroleptic) luminescent compound doping material with 2 or 1 chelating main ligands with longer emission wavelength containing N atoms and noble metal iridium. Due to the natural transfer effect of emission wavelength from high energy (or short wavelength) to low energy (or long wavelength), the hybrid or heteroleptic metal complex material eventually exhibits the main ligand luminescence wavelength under photo-or electro-excitation conditions. Thus, in a heteroleptic iridium complex, the ligands which determine the final color, generally lower in energy and longer in emission wavelength, are the primary ligands, while the other, non-developing ligands are the secondary ligands. According to this energy transfer principle, in recent years, it has been reported that the sublimation temperature is lowered by using a hybrid complex to improve the vapor deposition processability, and for example, patent applications US20100244004 and CN102439019A report that 6-methyl-2-phenylpyridine is used as a heteroligand, and the molecular weight is lowered to improve the homoligand-complex light-emitting compound (a) which is difficult to sublime, and the obtained heteroligand-complex light-emitting compound (B) has a constant light-emitting wavelength but a low sublimation temperature and is easy to sublime.
(A) Homoleptic iridium complex luminescent compounds: difficult to sublime (B): heteroleptic iridium complex luminescent compounds: sublimation while some sublimation temperatures may be reduced by using the above-described reduced molecular weight, or chelating ancillary ligands with smaller conjugated chromophores, the increasing OLED fabrication requirements are often not met.
In order to improve the service life of green-light organic metal complexes, the U.S. patent applications US.Pat.appl.20200199163 and 20200048290 use mixed deuterated-alkyl substituted pyridine and condensed aromatic heterocycle to form a luminescent ligand, and use the deuterated partial alkyl on the phenylpyridine auxiliary ligand or main ligand to obtain a novel green luminescent metal iridium complex with improved service life, but the problem of difficult purification due to the increase of molecular weight is difficult to dissolve, or the defects of difficult purification by sublimation and difficult preparation of OLED devices by vacuum sublimation evaporation are overcome.
It has been reported that the use of trifluoromethyl groups for the pyridine ring results in a red shift of the luminescent compound to a deep red emission (U.S. Pat. No. 2015/0053937, J-H.Kim, et al; CN103694277, Prunus et al). The use of fluoro or trifluoromethyl groups for the phenyl groups on the bonded pyridine ring can lead to blue-shifting of the luminescent iridium complex to deeper blue materials (JP2013-197323, ep1191611a2.us2014/0367647a1, CN 104004026). It is obvious that the direct bonding of the fluoroalkane to the luminescent ligand not only deactivates the ligand and reduces the reactivity and yield of further complex formation, but also causes a problem of a decrease in the luminous efficiency of the luminescent complex.
Disclosure of Invention
In view of the above-mentioned shortcomings of the prior art, the present invention provides a method for increasing molecular weight, but reducing sublimation temperature and improving solubility by considering the defects of difficult dissolution and difficult sublimation of the luminescent ligand iridium complex constructed by the condensed aromatic heterocycle of the existing green organic metal luminescent complex and pyridine or derivatives thereof, and combines the more developed hole injection capability (dominant HOMO) of the condensed aromatic heterocycle and the pyridine (dominant LUMO) or derivatives thereof which dominates the electron injection capability to obtain a novel organic luminescent material. The process is likewise suitable for obtaining novel yellow organometallic iridium complexes. The method for increasing molecular weight, reducing sublimation temperature and improving solubility relates to the use of phenyl pyridine substituted by partially fluorinated alkyl as an auxiliary ligand, develops an organic green and yellow metal iridium complex with solubilization and self-lubricating effects, can increase the solubility of the whole heteroleptic iridium metal complex, is beneficial to solution purification or solution coating processing, and can obviously reduce the sublimation temperature of the heteroleptic iridium complex with the same size or even with increased molecular weight on the premise of not influencing the luminescence property, thereby being beneficial to dissolving and purifying materials, being beneficial to reducing heating energy consumption and saving heating cost, and more importantly, promoting the film-forming temperature for processing OLED devices to be far away from the thermal degradation temperature of luminescent materials, thereby being beneficial to the engineering manufacture of OLED devices. Partially fluorinated alkyl substitution, we have surprisingly found that it also has the advantage of increasing the device aging lifetime.
Specifically, the technical scheme adopted by the invention is to disclose a luminescent organometallic iridium heterocomplex, which has a structure shown in a general formula (1) as follows:
wherein h is 1-4, k is 0-2, and m is 1-12 in the mixed alkyl-fluoroalkyl group in the phenylpyridine auxiliary ligand; p ═ 1 or 2 in the phenylpyridine ancillary ligands; y in the auxiliary ligand is selected from H, D, alkyl with carbon atom less than 12, cycloalkyl with carbon atom less than 12, fluorine-containing alkyl with carbon atom less than 12, phenyl, substituted phenyl, fluorenyl, substituted fluorenyl, pyridyl, substituted pyridyl, carbazolyl, benzofuranyl, benzothienyl, condensed aromatic heterocycle with carbon atom less than 12, F, Cl and NO2One or more chemically crosslinkable groups, or secondary amines bonded to the nitrogen atom-N (RR)2Secondary amine, wherein R is alkyl with carbon atom less than 12, cycloalkyl with carbon atom less than 12, phenyl, substituted phenyl, fluorenyl, substituted fluorenyl, benzofuranyl, benzothienyl, carbazolyl; q, m and n are the number of substituents on the aromatic heterocyclic ring, and can be 1-4;
ar in the ligand is the following condensed aromatic heterocyclic ring:
x ═ S, O in fused aromatic heterocycles; r1, R2, R3 and R4 are H, D, alkyl having less than 12 carbon atoms, cycloalkyl having less than 12 carbon atoms, fluoroalkyl having less than 12 carbon atoms, phenyl, substituted phenyl, fluorenyl, substituted fluorenyl, pyridyl, substituted pyridyl, carbazolyl, benzofuranyl, benzothienyl, fused aromatic heterocycle having less than 12 carbon atoms, F, Cl, Br or secondary amine bonded to nitrogen-N (RR)2And R in the secondary amine is alkyl with a carbon atom less than 12, cycloalkyl with a carbon atom less than 12, phenyl, substituted phenyl, fluorenyl, substituted fluorenyl, benzofuranyl, benzothienyl or carbazolyl.
Document us patent application us.pat. appl.20200017536 discloses the use of alkyl substituted pyridines in combination with fused cyclic naphthalenes to obtain yellow metal iridium organic complex luminescent materials with enhanced lifetime of OLED devices, but using acetylacetone as an auxiliary ligand in view of the problem of increased sublimation temperature. But because the O-Ir bonding energy in the acetylacetone or the derivative auxiliary ligand is smaller, the thermal decomposition temperature of the complex is not reduced enough. According to the scope of the patent, phenyl-pyridine is used as an auxiliary ligand, or an N-Ir bonding auxiliary ligand, has better heat resistance than acetylacetone or derivatives thereof, and is expressed by that the thermal decomposition weight loss temperature is increased, thereby expanding the operation range of the industrial evaporation material film and the industrial sublimation purification temperature.
However, conventionally, the use of a more advanced conjugated Ar fused ring to form a light-emitting ligand with pyridine or a substituted derivative thereof has often caused a problem of sublimation difficulty due to an increase in the molecular weight of the light-emitting complex. The invention provides an organic luminescent iridium complex, wherein a poly-fluorocarbon mixture is introduced into a phenylpyridine auxiliary ligand, and the formed fluorine-containing carbon alkyl metal complex greatly improves the original luminescent iridium complex Ir (L)3The purification difficulty caused by poor solubility effectively reduces the sublimation or vacuum thermal evaporation temperature, saves the heat energy consumption,the possibility of thermal decomposition of the organic light-emitting material during the evaporation process is reduced. The general formula for the polycarbofluoroalkanes herein is: - (CH)2)hCHk[CmF(2m+1)]3-kWherein h is 1-4; k-0-2, m-1-12, that is, the polycarbofluoroalkanes are different from halogen and F substitutions and also different from-CF3Substituted, but alkyl-fluoroalkane hybrids, in which the bond to the ancillary ligand phenylpyridine or the primary ligand is through the normal alkyl group, ensure that the organometallic complex's optoelectronic properties, complex-forming ability, etc. do not suffer from fluorine deactivation, or halogen deactivation. The organic light-emitting complex is applied to an OLED light-emitting device and also shows the prolongation of the service life of the device.
In the mixed alkyl-fluoroalkyl group of the general formula (1), h is 1-4, so that the direct connection of the carbon atom connected with fluorine to the pyridine ring is avoided to influence the photoelectric property of the auxiliary ligand or the complex forming activity of the auxiliary ligand.
In the scope of the present invention, the fluorine-containing auxiliary heteroligands can in principle hybridize with the luminescent main ligands in various combinations with metallic iridium to form a series of novel luminescent metal complexes, wherein the heteroleptic iridium metal complexes formed by pyridine (and substituted derivatives thereof) and fused aromatic heterocycles a, B or C include, but are not limited to, the following yellow-emitting electroluminescent complexes (table 1):
in the scope of the present invention, the fluorine-containing auxiliary heteroligands can be hybridized with the luminescent main ligand in various combinations to form a series of novel luminescent metal complexes with metallic iridium, wherein the heteroleptic iridium metal complexes formed by pyridine (and substituted derivatives thereof) and fused aromatic heterocyclic rings D, E or F include, but are not limited to, the following electroluminescent green iridium complexes (Table 2):
the substitution of the fluorocarbon chain on the auxiliary ligand phenyl-pyridine (and the substitution derivative thereof) brings better solubility, so that the organic luminescent complex can be more easily subjected to solution film formation, such as ink-jet printing, blade coating, spin coating and the like to prepare a luminescent layer. In order to facilitate the preparation of the multilayer OLED, after the soluble luminescent complex is formed into a film by adopting a solution, the invention also provides an organic luminescent material which can be further chemically crosslinked and converted into insoluble infusible functional organic luminescent materials. By including at least one chemical crosslinking group in the heteroleptic iridium metal complex. Chemical crosslinking groups can in principle be used in a wide variety, and there are numerous chemically crosslinkable groups in the literature, where the crosslinking groups suitable for the invention are selected from vinyl, acrylate or trifluorovinyl groups. When the crosslinking groups are heated to 160 ℃, intermolecular crosslinking can be carried out to form a network structure, and the network structure becomes insoluble and infusible macromolecules. On the other hand, these crosslinking groups can also promote chemical crosslinking under sufficiently strong UV light.
In the context of the present invention, the organometallic light-emitting complex with acrylate cross-linking comprises the following general structural formula, wherein L represents a light-emitting ligand:
the following crosslinking reaction occurs under the irradiation of heat or strong ultraviolet light, (3) insoluble and infusible macromolecular networks can be formed:
within the scope of the present invention, the organometallic light-emitting complex with styrene cross-linkable comprises the following general structural formula (4):
the following crosslinking reaction occurs under the irradiation of heat or strong ultraviolet light, (4) insoluble and infusible macromolecular networks can be formed:
in the context of the present invention, the organometallic light-emitting complex with trifluoroethylene crosslinkable comprises the following general structural formula (5):
under the irradiation of heat or strong ultraviolet light, the following crosslinking reaction occurs, (5) insoluble infusible macromolecular network is formed:
l in the general formula (3), (4) or (5) represents a light-emitting ligand formed by pyridine-fused aromatic heterocycle Ar. In principle, many electroluminescent complexes are accessible from a number of compounds according to the general formula (3), (4) or (5) of the crosslinkable organometallic light-emitting complex, typical compounds including, but not limited to, the following yellow light-emitting crosslinkable compounds (Table 3):
in principle, a number of compounds can be used to achieve the electroluminescent complexes according to the general formula (3), (4) or (5) of the crosslinkable organometallic light-emitting complexes, typical compounds including but not limited to the following green-emitting crosslinkable compounds (Table 4):
to obtain fluorine-containing ancillary heteroligands and organometallic complexes thereof, they can be prepared by various chemical preparation methods, such as Suzuki reactions, Grignard reactions or ring closure reactions, or other known synthetic routes. Specifically, a synthetic route is as follows, reaction formula I is that bromide reacts with butyl lithium to obtain a fluorine-containing auxiliary ligand 2; ancillary ligands 2 with IrCl3Or a hydrate thereof forms a chloro-bridged compound 3 of an auxiliary ligand-Ir; the chlorine bridge compound forms a more active preliminary complex 5 with a silver salt, such as silver triflate; the preliminary complex 5 and the bidentate chelate luminescent ligand L containing N atom form the final heteroleptic organometallic iridium luminescent complex 7 (final total yield 45-60%).
Reaction trial I: preparation of bis-ancillary ligand organometallic iridium complexes
In the context of the present invention, Ar in the ligand is the following fused aromatic heterocycle:
x ═ S, O in fused aromatic heterocycles; r1, R2, R3 and R4 are H, D, alkyl having less than 12 carbon atoms, cycloalkyl having less than 12 carbon atoms, fluoroalkyl having less than 12 carbon atoms, phenyl, substituted phenyl, fluorenyl, substituted fluorenyl, pyridyl, substituted pyridyl, carbazolyl, benzofuranyl, benzothienyl, fused aromatic heterocycle having less than 12 carbon atoms, F, Cl, Br or secondary amine bonded to nitrogen-N (RR)2And R in the secondary amine is alkyl with a carbon atom less than 12, cycloalkyl with a carbon atom less than 12, phenyl, substituted phenyl, fluorenyl, substituted fluorenyl, benzofuranyl, benzothienyl or carbazolyl.
The organic light-emitting metal complex disclosed by the invention can be applied to an organic light-emitting diode or an electroluminescent device OLED. The invention also discloses an organic electroluminescent device, which consists of the following parts:
(a) a cathode;
(b) an electron injection layer;
(c) an anode;
(d) a hole injection layer;
(e) a light-emitting layer sandwiched between the electron injection layer and the hole injection layer, wherein the light-emitting layer contains the following metal complex disclosed in the present invention (i.e., the light-emitting metal iridium complex (hybrid iridium complex) of the present invention), and has a structure represented by the following general formula (1):
wherein h is 1-4, k is 0-2, and m is 1-12 in the mixed alkyl-fluoroalkyl group in the phenylpyridine auxiliary ligand;
p ═ 1 or 2 in the ancillary ligands;
y in the auxiliary ligand is selected from H, D, alkyl with carbon atom less than 12, cycloalkyl with carbon atom less than 12, fluorine-containing alkyl with carbon atom less than 12, phenyl, substituted phenyl, fluorenyl, substituted fluorenyl, pyridyl, substituted pyridyl, carbazolyl, benzofuranyl, benzothienyl, condensed aromatic heterocycle with carbon atom less than 12, F, Cl and NO2One or more chemically crosslinkable groups, or secondary amines bonded to the nitrogen atom-N (RR)2Secondary amine, wherein R is alkyl with carbon atom less than 12, cycloalkyl with carbon atom less than 12, phenyl, substituted phenyl, fluorenyl, substituted fluorenyl, benzofuranyl, benzothienyl, carbazolyl;
q, m and n are the number of substituents on the aromatic heterocyclic ring, and can be 1-4;
ar in the ligand is the following condensed aromatic heterocyclic ring:
x ═ S, O in fused aromatic heterocycles; r1, R2, R3 and R4 are H and D, alkyl with carbon atom less than 12, cycloalkyl with carbon atom less than 12, fluorine-containing alkyl with carbon atom less than 12, phenyl, substituted phenyl, fluorenyl, substituted fluorenyl and pyridylSubstituted pyridyl, carbazolyl, benzofuranyl, benzothienyl, fused aromatic heterocycle having less than 12 carbon atoms, F, Cl, Br or secondary amine bonded to a nitrogen atom-N (RR)2And R in the secondary amine is alkyl with a carbon atom less than 12, cycloalkyl with a carbon atom less than 12, phenyl, substituted phenyl, fluorenyl, substituted fluorenyl, benzofuranyl, benzothienyl or carbazolyl.
The luminescent metal iridium complex (hybrid iridium complex) is applied to an organic light emitting diode, and is usually mixed with a Host material (Host) to form a luminescent layer by using the luminescent metal complex as a dopant. The mixing of the luminescent dopant compound in the host material is beneficial to increasing the efficiency of luminescent molecules, reducing the change of luminescent colors under different electric fields and simultaneously reducing the dosage of expensive luminescent dopants. The mixed film can be formed by vacuum co-evaporation, or by mixing and dissolving in solvent, spin coating, spray coating or solution printing. The invention also comprises the application of the luminescent material in organic light-emitting devices (OLED organic light-emitting diodes). As organic semiconductors, in principle the materials described can be applied as charge transport layers, blocking layers. From the economical point of view, the application as a light-emitting layer is more important. When used as a light emitting layer, in order to improve light emitting efficiency, it is necessary to avoid aggregation of light emitting molecules as much as possible and to use the following general device structure including:
a base material such as glass, metal foil, or polymer film;
an anode, such as transparent conductive indium tin oxide;
a cathode, such as conductive aluminum or other metal;
one or more organic semiconductors, such as an electron injection layer between the light-emitting layer and the cathode, a hole injection layer between the light-emitting layer and the anode, wherein the emission layer contains the phosphorescent light-emitting material in admixture with a host material. The light-emitting layer is typically doped with a light-emitting (wt) material at a concentration of less than 50%, preferably 0.2 to 20%, more preferably 2-15%. Of course, the host material may be a mixture of more than one material, in which case the smaller amount is the auxiliary host material and the larger amount is the main host material. An organic light emitting device having improved luminous efficiency can be obtained by incorporating an organometallic iridium complex having a shorter emission wavelength as a sensitizer in a light emitting layer of an organic electroluminescent device, for example, a green light emitting material sensitizer in an amount of 1 to 20% in a light emitting layer of a yellow light emitting device, and a yellow light emitting material sensitizer in an amount of 1 to 20% in a red light emitting device. The same luminescent layer can be doped with red light, green light and blue light doped luminescent materials at the same time to obtain a mixed white light luminescent device.
The luminescent layer of the luminescent device contains the luminescent material, and the luminescent layer is formed by a co-evaporation or solution coating method with a main body material or a main body material and an auxiliary main body material; the thickness of the luminescent layer is 5-50 nm, and the triplet state energy level of the host material is 2.2-2.9eV, which depends on the luminescent wavelength. If the material is blue electrophosphorescent, the triplet state energy level of the host material is more than 2.75 eV; if the material is green electrophosphorescent, the triplet state energy level of the host material is more than 2.40 eV; in the case of red-emitting electrophosphorescence, the triplet level of the host material should be greater than 2.2 eV.
As green, yellow light emitting OLED devices, many literature reported host materials can be used, wherein the host materials include, but are not limited to, the following structural compounds:
the luminescent material disclosed by the invention has the advantages and beneficial effects that: the invention uses partial fluorinated alkyl to replace phenyl-pyridine auxiliary ligand with solubilization and self-lubricating functions, in particular to introduce fluorine-containing alkyl on the pyridine ring, which can be partial fluorinated alkyl. The self-lubricating function of the halothane not only increases the solubility of the conjugated iridium complex, but also reduces the sublimation temperature, so that the original luminescent iridium complex which is difficult to dissolve and purify, difficult to sublimate and purify, high in efficiency, long in service life and difficult to sublimate and evaporate and prepare the OLED device becomes an easily-soluble, easily-sublimable and easily-scaled evaporation and preparation material for the OLED device. Therefore, the problems that a light-emitting ligand consisting of novel high-efficiency and long-life green and yellow light materials, pyridine or derivatives thereof and condensed aromatic heterocyclic rings, and a heterocomplex formed by metal iridium are difficult to purify and difficult to sublimate or the problem that the light-emitting layer of the OLED is easy to decompose due to high sublimation temperature in the process of evaporating the light-emitting layer are solved. Unexpectedly, unlike the auxiliary ligand or the halogen substitution or trifluoromethyl substitution on the luminescent ligand, which brings about a reduction in the luminous efficiency and a passivation of the auxiliary luminescent ligand to form the final organometallic complex, the partial fluorinated alkyl substitution overcomes these disadvantages and brings about the hydrophobicity of the organic luminescent metallic iridium complex, thereby achieving an effect of extending the lifetime of the device. The mixed alkyl-fluoroalkyl substituted auxiliary ligand phenylpyridine can further comprise a crosslinkable group, so that an insoluble and infusible light-emitting layer can be formed by thermal crosslinking after an OLED light-emitting layer is manufactured by a solution method or ink-jet printing conveniently, the whole OLED light-emitting device can be manufactured by continuously using the solution method or ink-jet printing, a polymer organic OLED light-emitting device can be formed, and the mechanical property and folding times of folding mobile phone display or television display curling are improved.
Drawings
Fig. 1 is a schematic diagram of an organic light emitting diode according to an embodiment.
Detailed Description
In order to make the aforementioned objects, features and advantages of the present invention comprehensible, specific embodiments accompanied with examples are described in detail below. In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention. The invention can be implemented in many ways other than those described herein and similar generalizations can be made by those skilled in the art without departing from the spirit of the invention. Therefore, the invention is not limited to the specific embodiments disclosed below.
Example 1: synthesis of luminescent compound Y13 containing 2-phenyl-6-trifluoromethylethyl-pyridine auxiliary ligand:
1.1 Synthesis of Compound Y13-2
3g of 5-trifluoroethyl-2-phenylpyridine, 1.41g of iridium trichloride trihydrate, 36mL of 2-ethoxyethanol and 12mL of distilled water were put into a 200mL three-necked flask, and after three times of replacement with nitrogen gas, the temperature was raised to 110 ℃ and the reaction solution was vigorously refluxed. After 20 hours of reaction, the temperature was reduced to about 30 ℃ and the mixture was stirred at room temperature for 0.5 hour, filtered, the solid was washed twice with 50mL × 2 of methanol and 50mL × 2 of n-hexane and dried to obtain 1.65g of a yellow solid with a yield of 84%.
1.2 Synthesis of Compound Y13-3
1.2g of the chloro-bridged compound, 71mL of dichloromethane and 5mL of methanol were added to a 100mL reaction vessel, replaced with nitrogen three times, stirred at room temperature for 16h, filtered through celite to remove the silver chloride, the solid was washed twice with 200mL of dichloromethane, and the dichloromethane was concentrated to give 1.4g of the silver salt Y13-3, and the next reaction was continued without treatment, yield: 99 percent.
1.3 Synthesis of Compound Y13
1.2g of silver salt Y13-3, 1.32g of ligand Y13-4 and 30mL of ethanol were placed in a 100mL three-necked flask, replaced with nitrogen 3 times, mechanically stirred, and then heated to reflux for 24 hours. After 24 hours of reaction, the temperature is reduced to room temperature (about 25 ℃), the mixture is stirred for 0.5 hour, then the mixture is filtered, the solid is pulped by 400mL of methanol, and finally the solid is passed through a silica gel column to obtain the yield of 99.5% Y13 of 70%. Molecule of formula C55H49F6IrN3The calculated molecular weight is: 1058.21, the sublimation temperature detected by Mass spectrometry is 332 ℃ when the Mass spectrometry detection is m/e 1058.35. Compound Y13 was dissolved in polystyrene THF solvent to make a 5% doped film on a quartz glass slide, whose emission PL spectrum was detected by UV380nm UV excitation, with a PL peak of 578nm yellow light.
Related physical data
According to the above synthetic chemistry principle and operation steps, the following organometallic iridium compound composed of fluorine-containing substituted heteroligand and luminescent ligand is synthesized, and the molecular weight and fragments of the molecule are verified by mass spectrometry of the listed complex, specifically shown in Table 4 below, wherein the yellow light emission wavelength is 550-580 nm; the green light emitting wavelength is at 510-545 nm:
TABLE 4
Example 2 solubility vs sublimation temperature experiment:
detecting Mass spectrum by directly injecting solid powder with DI-Mass Instrument, and detecting sublimation temperature (at fixed vacuum degree of 10) when molecular Mass spectrum peak appears-5torr), the following sublimation temperature results were obtained:
table 5: comparison of sublimation temperature and solubility of yellow light complex experimental results:
the results show that the fluoroalkyl-substituted yellow metallic iridium complex Y13 has the effects of reducing the sublimation temperature and increasing the solubility compared with Ref.1 complexes under the condition of the same number of carbon atoms in a similar luminescent structure; in addition, the TGA thermal decomposition temperature of Y13 is higher than that of the acetylacetone-assisted ligand yellow-light metallic iridium complex ref.2. That is, in the case of using the same light-emitting ligand, the sublimation temperature of the complex formed by the simplest acetylacetone auxiliary ligand is too close to the thermal decomposition temperature (less than 50 ℃), which easily causes thermal decomposition during the process of preparing an OLED device by sublimation purification or vapor deposition film formation, and the emission wavelength of the complex shifts to orange. Although the thermal decomposition temperature of the light-emitting complex using the phenylpyridine auxiliary ligand Ref.1 is increased, the sublimation temperature is also increased due to the increase of the molecular weight (relative to Ref.2), so that the process of preparing an OLED device by vapor deposition film forming is not facilitated.
Table 6: green light complex sublimation temperature versus solubility experimental results:
the above results show that the fluoroalkane-substituted green-emitting metal iridium complex G8 has the effects of reducing the sublimation temperature and increasing the solubility compared with Ref.3 complexes under the condition of the same number of carbon atoms of similar light-emitting structures. Although the molecular weight of the light-emitting complex using the phenylpyridine auxiliary ligand Ref.3 is smaller, the sublimation temperature of the light-emitting complex is higher by 26 ℃, and the light-emitting complex is not beneficial to the processes of sublimation purification and evaporation film-forming preparation of OLED devices.
Example 3: application example of vacuum evaporation device preparation:
at a background vacuum of 10-5In multi-source evaporation OLED preparation equipment of Pa, the following device structure is adopted:
luminescent dopants
Different host materials and emitting dopants were used for comparison in OLED light emitting devices. The vacuum deposition rates of the organic layers and the electrodes are shown in Table 5.
Table 7: preparation conditions of phosphorescent OLED device (9% of dopant weight concentration in light-emitting layer)
Table 8: yellow OLED device performance (1000 Cd/cm)2Under illumination); LT (LT)80％Lifetime @60mA/cm2
As can be seen from the comparison of the device performances in Table 8, the yellow light-emitting dopant compounds Y2(Ar is a fused thiophene ring), Y5(Ar is a naphthalene ring), Y8(Ar is benzofuran), and Y13(Ar is a substituted naphthalene ring) of the OLED devices obtained from the yellow light-emitting dopant compounds Y2(Ar is a fused thiophene ring), Y5(Ar is a naphthalene ring), and Y13(Ar is a substituted naphthalene ring) are compared with the comparative light-emitting material Ref.180％(@40mA/cm2) Longer.
Table 9: green OLED device Performance (1000 Cd/cm)2Under illumination); LT (LT)80％Lifetime h @60mA/cm2
As can be seen from the comparison of device performances in Table 9, the green light emitting dopant compounds of the present invention, G1(Ar is a fused ring of naphthalene thiophene), G5(Ar is a ring of naphthalene benzothiophene), G8(Ar is a nitrogen substituted benzofuran), and G13(Ar is a ring of naphthalene thiophene) give accelerated lifetime LT of OLED device, compared to the comparative light emitting material Ref.380％(@60mA/cm2) Longer. The comparative luminescent material Ref.4 does not contain condensed aromatic heterocyclic luminescent ligands, and the accelerated aging life of OLED devices thereof is inferior to that of all other devices。
Example 4: preparing an organic light-emitting device OLED light-emitting layer by solution spin coating:
after solvent and plasma cleaning is carried out on the surface of conductive glass ITO, PEDOT conductive polymer is spin-coated in solution to be used as a hole injection layer, poly (triphenylamine-9.9-diheptane fluorene) solution spin-coating is used as a hole transmission layer, then 2% of main material X-Host/the green light or red light or yellow light material (doping concentration is 4% by weight) mixed solution is spin-coated, and the film is heated to 160 ℃ under nitrogen for 30 minutes to be insoluble; then spin-coating a layer with the solution
Finally reaching a background vacuum of 10-5Evaporation electron injection layer in multi-source evaporation OLED preparation equipment of handkerchief
And preparing the OLED device. The host material is also a crosslinkable compound:
table 10: the performance of the cross-linkable luminescent layer OLED device prepared by solution spin coating is as follows:
the performance of the device reaches the performance similar to that of a vacuum evaporation device, but the device has the advantages that a light-emitting layer is obtained without vacuum operation, and the equipment cost is reduced.
The foregoing is merely a preferred embodiment of the invention and is not intended to limit the invention in any manner. Those skilled in the art can make numerous possible variations and modifications to the disclosed embodiments, or modify equivalent embodiments, without departing from the scope of the invention, using the teachings disclosed above. Therefore, any simple modification, equivalent change and modification made to the above embodiments according to the technical essence of the present invention are still within the protection scope of the technical solution of the present invention, unless the content of the technical solution of the present invention is departed from.
Claims (9)
1. An organic light-emitting device, characterized in that said light-emitting device is composed of:
(a) a cathode;
(b) an electron injection layer;
(c) an anode;
(d) a hole injection layer;
(e) a light-emitting layer sandwiched between the electron-injecting layer and the hole-injecting layer, wherein the light-emitting layer contains a light-emitting organometallic iridium heterocomplex having a structure represented by the following general formula (1):
wherein h is 1-4, k is 0-2, and m is 1-12 in the mixed alkyl-fluoroalkyl group in the phenylpyridine auxiliary ligand; p is 1 or 2; y in the ancillary ligands is selected from H, D, alkyl of less than 12 carbon atoms, cycloalkyl of less than 12 carbon atoms, fluoroalkyl of less than 12 carbon atoms, phenyl, substituted phenyl, fluorenyl, substituted fluorenyl, pyridyl, substituted pyridyl, carbazolyl, benzofuranyl, benzothienyl, fused aromatic heterocycle of less than 12 carbon atoms, F, Cl, NO2, one or more chemical crosslinking groups, or a secondary amine-n (rr)2 bonded to a nitrogen atom, wherein R is alkyl of less than 12 carbon atoms, cycloalkyl of less than 12 carbon atoms, phenyl, substituted phenyl, fluorenyl, substituted fluorenyl, benzofuranyl, benzothienyl, carbazolyl;
q, m and n are the number of substituents on the aromatic heterocyclic ring, and can be 1-4;
ar in the ligand is the following condensed aromatic heterocyclic ring:
x ═ S, O in fused aromatic heterocycles; r1, R2, R3 and R4 are H and D, alkyl with the carbon atom less than 12, cycloalkyl with the carbon atom less than 12, fluorine-containing alkyl with the carbon atom less than 12, phenyl, substituted phenyl, fluorenyl, substituted fluorenyl, pyridyl, substituted pyridyl, carbazolyl, benzofuranyl, benzothienyl, fused aromatic heterocycle with the carbon atom less than 12, F, Cl, Br or secondary amine-N (RR)2 bonded with nitrogen atom, R in the secondary amine is alkyl with the carbon atom less than 12, cycloalkyl with the carbon atom less than 12, phenyl, substituted phenyl, fluorenyl, substituted fluorenyl, benzofuranyl, benzothienyl and carbazolyl.
2. The organic light emitting device of claim 1, wherein Y in the light emitting organometallic iridium heterocomplex comprises at least one chemical crosslinking group selected from the group consisting of styryl, acrylate, and trifluorovinyl.
3. The luminescent organometallic iridium heterocomplex according to claim 2, characterized in that the crosslinkable organic luminescent complex is a yellow luminescent complex as follows:
4. the luminescent organometallic iridium heterocomplex of claim 2, wherein the crosslinkable organic luminescent complex is a green luminescent complex of:
5. a luminescent organometallic iridium heterocomplex according to claim 2, 3 or 4, characterised in that the crosslinkable organic luminescent complex forms an insoluble, infusible crosslinked network structure upon heating to 160 ℃:
wherein L represents a luminescent ligand formed by pyridine and a condensed aromatic heterocycle.
6. The organic light-emitting device according to claim 1, wherein the light-emitting organometallic iridium heterocomplex in the organic light-emitting device is an organometallic complex containing a condensed aromatic heterocycle a, B or C, comprising a yellow light-emitting complex as follows:
7. the organic light-emitting device according to claim 1, wherein the light-emitting organometallic iridium heterocomplex in the organic light-emitting device is an organometallic complex containing a condensed aromatic heterocycle of D, E or F, comprising a green light-emitting complex of:
8. the organic light-emitting device according to claim 1, wherein when the organometallic complex in the light-emitting layer is the light-emitting organometallic iridium heterocomplex of claim 3 or 6, the organic light-emitting device emits yellow light.
9. The organic light-emitting device according to claim 1, wherein when the organometallic complex in the light-emitting layer is the light-emitting organometallic iridium heterocomplex according to claims 4 and 7, the organic light-emitting device emits green light.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110158361.9A CN112961187A (en) | 2021-02-05 | 2021-02-05 | Organic luminescent metal iridium complex and application of organic electroluminescent device thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110158361.9A CN112961187A (en) | 2021-02-05 | 2021-02-05 | Organic luminescent metal iridium complex and application of organic electroluminescent device thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112961187A true CN112961187A (en) | 2021-06-15 |
Family
ID=76274097
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110158361.9A Pending CN112961187A (en) | 2021-02-05 | 2021-02-05 | Organic luminescent metal iridium complex and application of organic electroluminescent device thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112961187A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4265626A3 (en) * | 2022-04-18 | 2024-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004107441A (en) * | 2002-09-17 | 2004-04-08 | Nippon Hoso Kyokai <Nhk> | Organic luminescent material, organic light-emitting element and display using the same |
| CN104004026A (en) * | 2014-06-09 | 2014-08-27 | 江西冠能光电材料有限公司 | Electronegative phosphor material |
| CN105111243A (en) * | 2015-08-27 | 2015-12-02 | 江西冠能光电材料有限公司 | Light-emitting metal iridium complex and organic electroluminescence device prepared from same |
| CN106831884A (en) * | 2017-03-22 | 2017-06-13 | 江西冠能光电材料有限公司 | Organic metal iridium complex and its organic electroluminescence device application |
| CN109796500A (en) * | 2018-10-31 | 2019-05-24 | 冠能光电材料(深圳)有限责任公司 | It is a kind of miscellaneous with metal complex and its electroluminescent organic luminescent device application |
| CN112300216A (en) * | 2019-07-30 | 2021-02-02 | 环球展览公司 | Organic electroluminescent material and device |
-
2021
- 2021-02-05 CN CN202110158361.9A patent/CN112961187A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004107441A (en) * | 2002-09-17 | 2004-04-08 | Nippon Hoso Kyokai <Nhk> | Organic luminescent material, organic light-emitting element and display using the same |
| CN104004026A (en) * | 2014-06-09 | 2014-08-27 | 江西冠能光电材料有限公司 | Electronegative phosphor material |
| CN105111243A (en) * | 2015-08-27 | 2015-12-02 | 江西冠能光电材料有限公司 | Light-emitting metal iridium complex and organic electroluminescence device prepared from same |
| CN106831884A (en) * | 2017-03-22 | 2017-06-13 | 江西冠能光电材料有限公司 | Organic metal iridium complex and its organic electroluminescence device application |
| CN109796500A (en) * | 2018-10-31 | 2019-05-24 | 冠能光电材料(深圳)有限责任公司 | It is a kind of miscellaneous with metal complex and its electroluminescent organic luminescent device application |
| CN112300216A (en) * | 2019-07-30 | 2021-02-02 | 环球展览公司 | Organic electroluminescent material and device |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4265626A3 (en) * | 2022-04-18 | 2024-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102413285B1 (en) | Phosphorescent materials | |
| Shao et al. | A Novel, Bipolar Polymeric Host for Highly Efficient Blue Electrophosphorescence: a Non‐Conjugated Poly (aryl ether) Containing Triphenylphosphine Oxide Units in the Electron‐Transporting Main Chain and Carbazole Units in Hole‐Transporting Side Chains | |
| Liang et al. | High‐Efficiency Red Phosphorescent Iridium Dendrimers with Charge‐Transporting Dendrons: Synthesis and Electroluminescent Properties | |
| KR101255233B1 (en) | Organometallic complexes and organic electroluminescence device using the same | |
| EP1534799A1 (en) | Organic light emitting materials and devices | |
| WO2017032143A1 (en) | Light-emitting metal iridium complex and organic electroluminescence device prepared therefrom | |
| Park et al. | Synthesis, characterization of the phenylquinoline-based on iridium (III) complexes for solution processable phosphorescent organic light-emitting diodes | |
| Chen et al. | An oligocarbazole-encapsulated heteroleptic red iridium complex for solution-processed nondoped phosphorescent organic light-emitting diodes with over 10% external quantum efficiency | |
| KR101338252B1 (en) | Cyclometalated transition metal complex and organic electroluminescence device using the same | |
| JP2007308498A (en) | Photoluminescent heteronuclear copper-iridium complex and organoelectroluminescent element obtained utilizing the same | |
| CN109796500B (en) | Hybrid metal complex and application of hybrid metal complex to organic electroluminescent device | |
| US7652136B2 (en) | Diarylaminofluorene-based organometallic phosphors and organic light-emitting devices made with such compounds | |
| KR101275809B1 (en) | Cyclometalated transition metal complex and organic electroluminescence device using the same | |
| CN115677743A (en) | Organic boron semiconductor compound and application thereof | |
| JP5000497B2 (en) | Electroluminescent materials and devices | |
| KR101863375B1 (en) | Ion-pairing soft salts based on organometallic complexes and their applications in organic light emitting diodes | |
| CN113135945A (en) | Organic boron semiconductor material and OLED device application | |
| Jung et al. | Deep‐red light‐emitting phosphorescent dendrimer encapsulated tris‐[2‐benzo [b] thiophen‐2‐yl‐pyridyl] iridium (III) core for light‐emitting device applications | |
| CN112961187A (en) | Organic luminescent metal iridium complex and application of organic electroluminescent device thereof | |
| Zhang et al. | Efficient electrophosphorescence based on 2-(9, 9-diethylfluoren-2-yl)-5-trifluoromethylpyridine iridium complexes | |
| EP1484380A1 (en) | Polymeric phosphors, process for production thereof, phosphorescent compositions and articles made by using the same | |
| CN112961191A (en) | Functional hybrid organic electroluminescent iridium complex and organic electroluminescent device thereof | |
| KR101414997B1 (en) | Luminescent multinuclear copper complex and organic electroluminescence device using the same | |
| JP5649029B2 (en) | Luminescent composition, organic electroluminescent device, and benzodifuran derivative | |
| Si et al. | Bright electrophosphorescent devices based on sterically hindered spacer-containing Cu (I) complex |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |