CN112687822A - Composition and organic electroluminescent element comprising same - Google Patents

Composition and organic electroluminescent element comprising same Download PDF

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CN112687822A
CN112687822A CN202011571782.6A CN202011571782A CN112687822A CN 112687822 A CN112687822 A CN 112687822A CN 202011571782 A CN202011571782 A CN 202011571782A CN 112687822 A CN112687822 A CN 112687822A
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王子兴
陈清泉
吕伯彦
吴空物
赵晓宇
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Zhejiang Huadisplay Optoelectronics Co Ltd
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Abstract

The invention belongs to the field of organic photoelectricity, and particularly relates to a composition containing an iridium metal complex and an organic compound and an organic electroluminescent element containing the composition, in particular to an organic electroluminescent diode, wherein the iridium metal complex has a structure shown in a formula (I), and the organic compound has a structural formula (II) or (III):
Figure DDA0002862937160000011
in the iridium metal complex formula (I), (L ^ Z) is selected from a formula (IV),

Description

Composition and organic electroluminescent element comprising same
Technical Field
The invention belongs to the field of organic electroluminescence, and particularly relates to a composition of an iridium metal complex and an organic compound, and an organic electroluminescent element containing the composition.
Background
As a novel display technology, the organic electroluminescent element has the unique advantages of self luminescence, wide viewing angle, low energy consumption, high efficiency, thinness, rich colors, high response speed, wide application temperature range, low driving voltage, capability of manufacturing flexible, bendable and transparent display panels, environmental friendliness and the like, can be applied to flat panel displays and new generation illumination, and can also be used as a backlight source of an LCD.
Since the invention of the 20 th century and the 80 th century, organic electroluminescent devices have been used in industry, such as display screens of mobile phones, but the current OLED devices have limited their wider application, especially large screen displays, due to low efficiency and short service life. And the most important factor restricting the wide application thereof is the performance of the organic electroluminescent material. Meanwhile, when an OLED device is operated by applying a voltage, joule heat is generated, so that organic materials are easily crystallized, and the lifetime and efficiency of the device are affected.
Since the ratio of the singlet excited state to the triplet excited state due to charge binding is theoretically estimated to be 1:3, the use of a small molecular fluorescent material is considered to be only 25% of the total energy available for light emission, and the remaining 75% of the energy is lost due to the non-light-emitting mechanism of the triplet excited state, so that the internal quantum efficiency limit of the fluorescent material is considered to be 25%. Professor Baldo and Forrest in 1998 discovered that triplet phosphorescence can be utilized at room temperature, and the upper limit of the original internal quantum efficiency is raised to 100%, and triplet phosphors are complex compounds composed of heavy metal atoms, and by utilizing the heavy atom effect, the strong spin-orbit coupling effect causes the energy levels of singlet excited states and triplet excited states to be mixed with each other, so that the originally forbidden triplet energy is relieved to emit light in the form of phosphorescence, and the quantum efficiency is greatly improved.
At present, almost all light emitting layers in an organic OLED module use a host-guest light emitting system mechanism, that is, a guest light emitting material is doped in a host material, and generally, the energy system of the organic host material is larger than that of the guest material, that is, the energy is transferred from the host to the guest, so that the guest material is excited to emit light. A commonly used phosphorescent organic host material such as CBP (4, 4' -bis (9-carbazolyl) -biphenyl) has a high efficiency and a high triplet energy level, and when it is used as an organic material, the triplet energy can be efficiently transferred from a light emitting organic material to a guest phosphorescent light emitting material. A commonly used organic guest material is an iridium metal complex.
The invention discovers that the combination of a specific organic compound and an iridium metal compound can be used as a light-emitting layer of an organic electroluminescent element to remarkably improve the current efficiency of the organic electroluminescent element, reduce the operating voltage of the element and prolong the service life of the element.
Disclosure of Invention
The invention aims to provide a composition of an iridium metal complex and an organic compound and an organic electroluminescent element comprising the composition.
The invention provides a composition of an iridium metal complex and an organic compound, wherein the iridium metal complex has a structure shown in a formula (I), and the organic compound has a structural formula (II) or (III):
Figure BDA0002862937140000021
preferably, in formula (I), X is selected from NR1, O, S, CR1R2, SiR1R2, O ═ P-R1 or B-R1; y is selected from N or C-R1;
(L ^ Z) is selected from structural formulas represented by formula (IV)
Figure BDA0002862937140000022
R1-R8, R11 are independently selected from hydrogen, deuterium, cyano, halogen, C1-C18 alkyl, C1-C18 alkoxy, C1-C18 alkylsilyl, C1-C18 alkoxysilyl, C6-C40 aryl, C1-C40 heteroaryl, substituted or unsubstituted arylether group, substituted or unsubstituted heteroarylether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamine group, substituted or unsubstituted arylsilicon group, substituted or unsubstituted heteroarylsilicon group, substituted or unsubstituted aryloxyside group, substituted or unsubstituted arylacyl group, substituted or unsubstituted heteroarylacyl group, substituted or unsubstituted phosphinyl groupAny one of them; r9, R10 is selected from any one of cyano, C1-C18 alkyl, C1-C18 alkoxy, C6-C40 aryl, C1-C40 heteroaryl, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl ether group, substituted or unsubstituted aryl acyl, substituted or unsubstituted heteroaryl acyl, and substituted or unsubstituted phosphinyl; all groups may be partially deuterated or fully deuterated. m is taken from 1 or 2, and m + n is 3; heteroaryl means containing B, N, O, S, P (═ O), Si, P at least one heteroatom;
in formula (II) and formula (III), X1 to X6 are CR or N; y1 to Y8 are CR or N, and at least 2 are N; l is absent or selected from single bond, O, S, CRR, SiRR, NR; a and B are each independently selected from C6-C30 aryl, C2-C30 heteroaryl; r is independently selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, aryl or heteroaryl substituted amine; n is an integer of 0 to 6; adjacent X or Y may form a ring; all groups may be partially deuterated or fully deuterated.
Preferably, the iridium metal complex of the present invention is selected from one of the following structures, but represents no limitation thereto:
Figure BDA0002862937140000031
wherein X1, X2, R to R11, A, B are the same as described above.
Preferably, R1 to R11 in the iridium metal complex of the present invention are selected from one of the following representative structural formulae, but do not represent and are not limited thereto:
Figure BDA0002862937140000032
preferably, the iridium metal complex of the present invention is selected from one of the following structures, but does not represent a limitation thereto:
Figure BDA0002862937140000041
Figure BDA0002862937140000051
Figure BDA0002862937140000061
Figure BDA0002862937140000071
Figure BDA0002862937140000081
Figure BDA0002862937140000091
Figure BDA0002862937140000101
Figure BDA0002862937140000111
Figure BDA0002862937140000121
Figure BDA0002862937140000131
the present invention provides compositions wherein the organic compound is preferably selected from the group consisting of compounds described in formula (II) -1 to II-7, but not limited thereto, when the structure of the organic compound is formula (II):
Figure BDA0002862937140000141
wherein X1 to X6, Y1 to Y8, L, R, n are the same as described above.
Preferably, one organic compound represented by formula (II) or formula (III) is selected from at least one of the following representative structures, but does not represent a limitation thereto:
Figure BDA0002862937140000151
Figure BDA0002862937140000161
Figure BDA0002862937140000171
Figure BDA0002862937140000181
Figure BDA0002862937140000191
Figure BDA0002862937140000201
Figure BDA0002862937140000211
Figure BDA0002862937140000221
Figure BDA0002862937140000231
Figure BDA0002862937140000241
Figure BDA0002862937140000251
Figure BDA0002862937140000261
Figure BDA0002862937140000271
Figure BDA0002862937140000281
Figure BDA0002862937140000291
Figure BDA0002862937140000301
Figure BDA0002862937140000311
Figure BDA0002862937140000321
Figure BDA0002862937140000331
Figure BDA0002862937140000341
Figure BDA0002862937140000351
Figure BDA0002862937140000361
Figure BDA0002862937140000371
Figure BDA0002862937140000381
Figure BDA0002862937140000391
Figure BDA0002862937140000401
Figure BDA0002862937140000411
Figure BDA0002862937140000421
Figure BDA0002862937140000431
Figure BDA0002862937140000441
Figure BDA0002862937140000451
Figure BDA0002862937140000461
Figure BDA0002862937140000471
Figure BDA0002862937140000481
Figure BDA0002862937140000491
Figure BDA0002862937140000501
Figure BDA0002862937140000511
Figure BDA0002862937140000521
Figure BDA0002862937140000531
Figure BDA0002862937140000541
Figure BDA0002862937140000551
Figure BDA0002862937140000561
Figure BDA0002862937140000571
Figure BDA0002862937140000581
Figure BDA0002862937140000591
Figure BDA0002862937140000601
Figure BDA0002862937140000611
Figure BDA0002862937140000621
Figure BDA0002862937140000631
Figure BDA0002862937140000641
Figure BDA0002862937140000651
Figure BDA0002862937140000661
Figure BDA0002862937140000671
Figure BDA0002862937140000681
Figure BDA0002862937140000691
Figure BDA0002862937140000701
Figure BDA0002862937140000711
Figure BDA0002862937140000721
the solvent used in the present invention is not particularly limited, and examples thereof include unsaturated hydrocarbon solvents such as toluene, xylene, mesitylene, tetralin, decahydronaphthalene, bicyclohexyl, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, halogenated saturated hydrocarbon solvents such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, etc., halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, trichlorobenzene, etc., ether solvents such as tetrahydrofuran, tetrahydropyran, etc., ester solvents such as alkyl benzoate, etc., which are well known to those skilled in the art.
The present invention also relates to an organic opto-electronic device comprising: a first electrode;
a second electrode facing the first electrode;
the organic functional layer is clamped between the first electrode and the second electrode;
wherein the light-emitting layer comprises the composition.
The mass percentage of the iridium metal complex in the formula (I) in the light-emitting layer of the organic electroluminescent device is 0.1-50%.
In the present invention, the organic electroluminescent element is an anode which can be formed by depositing metal, an oxide having conductivity, or an alloy thereof on a substrate by a sputtering method, electron beam evaporation, vacuum deposition, or the like; and sequentially evaporating a hole injection layer, a hole transport layer, a luminescent layer, a hole blocking layer and an electron transport layer on the surface of the prepared anode, and then evaporating a cathode. The organic electroluminescent device is prepared by vapor deposition of the cathode, the organic layer and the anode on the substrate except the above method. The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, and an electron transport layer. In the invention, the organic layer is prepared by adopting a high polymer material according to a solvent engineering (spin-coating), tape-casting (tape-casting), doctor-blading (sector-Printing), Screen-Printing (Screen-Printing), ink-jet Printing or Thermal-Imaging (Thermal-Imaging) method instead of an evaporation method, so that the number of the device layers can be reduced.
The materials used for the organic electroluminescent element according to the present invention may be classified into top emission, bottom emission, or double-sided emission. The compounds of the organic electroluminescent device according to the embodiment of the present invention can be applied to the aspects of the organic electroluminescent element such as an organic light emitting cell, an illuminating OLED, a flexible OLED, an organic photoreceptor, an organic thin film transistor and the like in a similar principle to the organic light emitting device.
The invention has the beneficial effects that:
the invention relates to a novel iridium metal complex and an organic compound composition, which have better thermal stability, the organic compound can balance the transport of holes and electrons, and the energy transmission between the organic compound and the iridium metal complex in the composition is more efficient.
Drawings
FIG. 1 is a structural diagram of an organic electroluminescent diode device according to the present invention.
Where 110 denotes a substrate, 120 denotes an anode, 130 denotes a hole injection layer, 140 denotes a hole transport layer, 150 denotes a light emitting layer, 160 denotes a hole blocking layer, 170 denotes an electron transport layer, 180 denotes an electron injection layer, and 190 denotes a cathode.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
In a preferred embodiment of the present invention, the OLED device according to the invention comprises a hole transport layer, which may preferably be selected from known or unknown materials, particularly preferably from the following structures, without representing the present invention being limited to the following structures:
Figure BDA0002862937140000741
in a preferred embodiment of the present invention, the hole transport layer contained in the OLED device of the present invention comprises one or more p-type dopants. Preferred p-type dopants of the present invention are, but do not represent a limitation of the present invention to:
Figure BDA0002862937140000742
in a preferred embodiment of the present invention, the electron transport layer may be selected from at least one of the compounds ET-1 to ET-13, but does not represent that the present invention is limited to the following structures:
Figure BDA0002862937140000751
the organic compounds referred to in the present invention are obtained by known synthetic methods.
The general synthesis steps of the iridium metal complex related to the formula (I) are as follows:
Figure BDA0002862937140000752
the general procedure is as follows,
(1) ligand 1(0.10 mol), IrCl are added under the protection of argon3.3H2Heating and refluxing a mixed solution of O (0.045 mol), 2-ethoxyethanol (300 ml) and water (100 ml) for 16-20 hours until a supernatant is obtained, detecting the content of the ligand 1 by using high performance liquid chromatography to be less than 5%, stopping heating, cooling to room temperature, performing suction filtration by using a Buchner funnel, leaching a filter cake by using a mixed solution of water and 2-ethoxyethanol, and drying to obtain a bridging dimer 2 or 3 of yellow powder, wherein the yield is 81-89%.
(2) Under the protection of argon, dropwise adding a tetrahydrofuran solution of a dichloro crosslinked dimer complex (2.2mmol) into a lithium salt solution (-78 ℃) formed by a ligand L ^ Z (2.4mmol) and butyllithium, slowly heating to room temperature, heating under reflux for 6 hours, stopping heating, cooling to room temperature, adding a proper amount of distilled water, and filtering to obtain a solid. The solid was dissolved in dichloromethane and passed through a short column of silica gel. Removing the solvent under reduced pressure, and washing the solid obtained by concentration with methanol and petroleum ether in sequence to obtain the final target product. Ligand 1 was obtained by custom synthesis. These are merely examples illustrating embodiments of the present invention and the scope of the present invention is not limited thereto.
Example 1: synthesis of Compound 1
Figure BDA0002862937140000761
Referring to the general synthetic route, lithium NN-dimethyl-phenylamidinate was used as lithium reagent in 73% yield of the final product. Mass spectrum m/z, theoretical 1093.48; found M + H: 1094.4.
example 2: synthesis of Compound 2
Figure BDA0002862937140000762
Referring to the general synthetic route, lithium NN-diethyl-phenylamidinate was used as lithium reagent in 72% yield of the final product. Mass spectrum m/z, theoretical 1093.49; found M + H: 1094.5.
example 3: synthesis of Compound 3
Figure BDA0002862937140000763
Referring to the general synthetic route, lithium NN-diisopropyl-phenylamidinate was used as lithium reagent in 78% yield of the final product. Mass spectrum m/z, theoretical 1241.61; found M + H: 1242.6.
example 4: synthesis of Compound 4
Figure BDA0002862937140000771
Referring to the general synthetic route, lithium NN-dimethyl-phenylamidinate was used as lithium reagent in 71% yield of the final product. Mass spectrum m/z, theoretical 1073.4; found M + H: 1074.4.
example 5: synthesis of Compound 5
Figure BDA0002862937140000772
Referring to the general synthetic route, lithium NN-diisopropyl-phenylamidinate was used as lithium reagent in 74% yield of the final product. Mass spectrum m/z, theoretical 1405.77; found M + H: 1406.7.
example 6: synthesis of Compound 6
Figure BDA0002862937140000773
Referring to the general synthetic route, lithium NN-di-tert-butyl-phenylamidinate was used as lithium reagent in 72% yield of the final product. Mass spectrum m/z, theoretical 1373.8; found M + H: 1374.8.
example 7: synthesis of Compound 7
Figure BDA0002862937140000781
Referring to the general synthetic route, lithium NN-diisopropyl-phenylamidinate was used as lithium reagent in 73% yield of the final product. Mass spectrum m/z, theoretical 1097.45; found M + H: 1098.4.
example 8: synthesis of Compound 8
Figure BDA0002862937140000782
Referring to the general synthetic route, lithium NN-di-tert-butyl-phenylamidinate was used as lithium reagent in 79% yield of the final product. Mass spectrum m/z, theoretical 1153.2; found M + H: 1154.2.
example 9: synthesis of Compound 9
Figure BDA0002862937140000783
Referring to the general synthetic route, lithium NN-diisopropyl-phenylamidinate was used as lithium reagent in 71% yield of the final product. Mass spectrum m/z, theoretical 1185.47; found M + H: 1186.4.
example 10: synthesis of Compound 10
Figure BDA0002862937140000784
Referring to the general synthetic route, lithium NN-dimethyl-phenylamidinate was used as lithium reagent in 75% yield of the final product. Mass spectrum m/z, theoretical 1241.52; found M + H: 1242.5.
example 11: synthesis of Compound 11
Figure BDA0002862937140000791
Referring to the general synthetic route, ligand represents lithium NN-diisopropyl-phenylamidinate as lithium reagent, and the yield of the final product is 74%. Mass spectrum m/z, theoretical 1181.55; found M + H: 1182.5.
example 12: synthesis of Compound 12
Figure BDA0002862937140000792
Referring to the general synthetic route, lithium NN-di-tert-butyl-phenylamidinate was used as lithium reagent in 78% yield of the final product. Mass spectrum m/z, theoretical 1265.64; found M + H: 1266.6.
example 13: synthesis of Compound 14
Figure BDA0002862937140000793
Referring to the general synthetic route, lithium NN-di-tert-butyl-phenylamidinate was used as lithium reagent in 75% yield of the final product. Mass spectrum m/z, theoretical 1113.46; found M + H: 1114.5.
manufacturing of OLED device:
a P-doped material P-1 to P-5 is evaporated on the surface or anode of ITO/Ag/ITO glass with the size of 2mm multiplied by 2mm in light emitting area or the P-doped material is co-evaporated with the compound in the table with the concentration of 1% to 50% to form a Hole Injection Layer (HIL) with the thickness of 5 nm to 100nm and a Hole Transport Layer (HTL) with the thickness of 5 nm to 200nm, then a light emitting layer (EML) (which can contain the compound) with the thickness of 10 nm to 100nm is formed on the hole transport layer, finally an Electron Transport Layer (ETL) with the thickness of 20 nm to 200nm and a cathode with the thickness of 50 nm to 200nm are formed by the compound in sequence, if necessary, an Electron Blocking Layer (EBL) is added between the HTL and the EML layer, and an Electron Injection Layer (EIL) is added between the ETL and the cathode. The OLEDs were tested by standard methods, as listed in table 1.
To better illustrate the practical gain effects of the present invention, comparative organic electroluminescent elements were prepared using the following commonly used iridium metal complex RD-1 and the iridium metal complexes of the present invention and organic compounds H-1 to H-14 as the main components to illustrate the superiority of the composition of the present invention.
Figure BDA0002862937140000801
In the specific embodiment, the structure of the top-emitting OLED device is on ITO/Ag/ITO-containing glass, HIL is HT-1: P-3(97:3 v/v%), and the thickness is 10 nanometers; HTL is HT-1, and the thickness is 100 nanometers; EBL is HT-8, thickness is 10 nm, EML is the composition of the invention, concretely, (H-1-H-14): (RD-1-RD-6) (97:3 v/v%), thickness is 35 nm, ETL is ET-13: LiQ (50:50 v/v%) with a thickness of 35 nm, then evaporating a cathode Yb of 1 nm, an Ag of 14 nm and an evaporated CPL layer of 70 nm. The characteristics of efficiency, operating voltage, life, etc. according to the above examples and comparative examples are shown in table 1 below.
TABLE 1
Examples EML Driving voltage (volt) Current efficiency (cd/A) LT95 (hours)
Comparison device 1 RD-1：H-1 4.0 40.3 126
Comparison device 2 RD-1：H-4 4.0 40.6 136
Comparison device 3 RD-1：H-5 3.9 42.3 188
Comparison device 4 RD-1：H-9 4.0 41.0 160
Comparison device 5 RD-1：H-14 3.8 42.6 190
Device example 1 Compound 1：H-1 3.8 55.1 186
Device example 2 Compound 2：H-1 3.8 57.2 280
Device example 3 Compound 4：H-1 3.7 57.3 295
Device example 4 Compound 7：H-1 3.8 54.6 298
Device example 5 Compound 9：H-1 3.9 55.6 285
Device example 6 Compound 11：H-1 3.8 55.9 288
Device example 7 Compound 1：H-5 3.7 57.9 302
Device example 8 Compound 2：H-5 3.7 60.0 309
Device example 9 Compound 4：H-5 3.7 60.1 306
Device example 10 Compound 7：H-5 3.7 57.3 280
Device example 11 Compound 9：H-5 3.7 58.3 297
Device example 12 Compound 11：H-5 3.7 58.7 310
Device example 13 Compound 1：H-14 3.6 56.7 288
Device example 14 Compound 2：H-14 3.6 58.9 270
Device example 15 Compound 4：H-14 3.6 59.1 290
Device example 16 Compound 7：H-14 3.6 56.2 286
Device example 17 Compound 9：H-14 3.6 57.2 268
Device example 18 Compound 11：H-14 3.6 57.6 272
As can be seen from Table 1, after the substitution planarization is introduced on the ligand structure, the current efficiency of the OLED device can be obviously improved and the driving voltage can be reduced by using the composition provided by the invention under the same conditions in the devices 1 to 18 and the comparative devices 1 to 5. Specifically, comparing the device 1 with the device examples 1-6, the combination provided by the invention has obvious advantages. If a new combination is adopted, namely the device examples 7 to 18, the operating voltage is obviously lower than that of the comparison devices 3 to 5, the luminous efficiency is higher, and the service life is prolonged. The composition provided by the invention has remarkable advantages and commercial application value.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.

Claims (12)

1. A composition is characterized by comprising an iridium metal complex and an organic compound, wherein the structural formula of the iridium metal complex is shown as a formula (I); the structural formula (II) or (III) of the organic compound
Figure FDA0002862937130000011
In formula (I), X is selected from NR1, O, S, CR1R2, SiR1R2, O ═ P-R1 or B-R1; y is selected from N or C-R1; (L ^ Z) is selected from structural formulas represented by the formula A,
Figure FDA0002862937130000012
R1-R8, R11 are independently selected from any one of hydrogen, deuterium, cyano, halogen, C1-C18 alkyl, C1-C18 alkoxy, C1-C18 alkylsilyl, C1-C18 alkoxysilyl, C6-C40 aryl, C1-C40 heteroaryl, substituted or unsubstituted arylether group, substituted or unsubstituted heteroarylether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamine group, substituted or unsubstituted arylsilicon group, substituted or unsubstituted heteroarylsilicon group, substituted or unsubstituted aryloxyside group, substituted or unsubstituted arylacyl group, substituted or unsubstituted heteroarylacyl group, substituted or unsubstituted phosphinyl group; r9, R10 is selected from cyano, C1-C18 alkyl, C1-C18 alkoxy, C6-C40 aryl, C1-C40 heteroaryl, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl ether group, substituted or unsubstituted aryl acyl, substituted or unsubstituted heteroaryl acyl, substituted or unsubstituted oxygenAny one of phosphine groups; all groups may be partially deuterated or fully deuterated. m is taken from 1 or 2, and m + n is 3; heteroaryl means containing B, N, O, S, P (═ O), Si, P at least one heteroatom;
in formula (II) and formula (III), X1 to X6 are CR or N; y1 to Y8 are CR or N, and at least 2 are N; l is absent or selected from single bond, O, S, CRR, SiRR, NR; a and B are each independently selected from C6-C30 aryl, C2-C30 heteroaryl; r is independently selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, aryl or heteroaryl substituted amine; n is an integer of 0 to 6; adjacent X or Y may form a ring; all groups may be partially deuterated or fully deuterated.
2. The composition of claim 1, wherein the iridium metal complex of formula (I) is selected from one of the following structures:
Figure FDA0002862937130000021
wherein X1, X2, R to R11, A, B are the same as described in claim 1.
3. The composition as claimed in claim 1, wherein R1 to R11 in the iridium metal complex of formula (I) are selected from one of the following representative structural formulae:
Figure FDA0002862937130000022
4. the composition as claimed in any one of claims 1 to 2, wherein the iridium metal complex of formula (I) is selected from one of the following representative structures:
Figure FDA0002862937130000031
Figure FDA0002862937130000041
Figure FDA0002862937130000051
Figure FDA0002862937130000061
Figure FDA0002862937130000071
Figure FDA0002862937130000081
Figure FDA0002862937130000091
Figure FDA0002862937130000101
Figure FDA0002862937130000111
Figure FDA0002862937130000121
5. the composition of claim 1, wherein formula (II) is selected from the group consisting of compounds of formula II-1 through II-7
Figure FDA0002862937130000131
Wherein X1 to X6, L, A, B, R, n are the same as in claim 1.
6. The composition of claim 1, wherein a and B are selected from the group consisting of those described by the following structures:
Figure FDA0002862937130000132
wherein X1 to X6, Y1 to Y8, L, R, n are the same as in claim 1.
7. The composition according to any one of claims 1 to 7, wherein the organic compound of formula (II) or formula (III) is selected from one of the following representative structures:
Figure FDA0002862937130000141
Figure FDA0002862937130000151
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Figure FDA0002862937130000171
Figure FDA0002862937130000181
Figure FDA0002862937130000191
Figure FDA0002862937130000201
Figure FDA0002862937130000211
Figure FDA0002862937130000221
Figure FDA0002862937130000231
Figure FDA0002862937130000241
Figure FDA0002862937130000251
Figure FDA0002862937130000261
Figure FDA0002862937130000271
Figure FDA0002862937130000281
Figure FDA0002862937130000291
Figure FDA0002862937130000301
Figure FDA0002862937130000311
Figure FDA0002862937130000321
Figure FDA0002862937130000331
Figure FDA0002862937130000341
Figure FDA0002862937130000351
Figure FDA0002862937130000361
Figure FDA0002862937130000371
Figure FDA0002862937130000381
Figure FDA0002862937130000391
Figure FDA0002862937130000401
Figure FDA0002862937130000411
Figure FDA0002862937130000421
Figure FDA0002862937130000431
Figure FDA0002862937130000441
Figure FDA0002862937130000451
Figure FDA0002862937130000461
Figure FDA0002862937130000471
Figure FDA0002862937130000481
Figure FDA0002862937130000491
Figure FDA0002862937130000501
Figure FDA0002862937130000511
Figure FDA0002862937130000521
Figure FDA0002862937130000531
Figure FDA0002862937130000541
Figure FDA0002862937130000551
Figure FDA0002862937130000561
Figure FDA0002862937130000571
Figure FDA0002862937130000581
Figure FDA0002862937130000591
Figure FDA0002862937130000601
Figure FDA0002862937130000611
Figure FDA0002862937130000621
Figure FDA0002862937130000631
Figure FDA0002862937130000641
Figure FDA0002862937130000651
Figure FDA0002862937130000661
Figure FDA0002862937130000671
Figure FDA0002862937130000681
Figure FDA0002862937130000691
Figure FDA0002862937130000701
Figure FDA0002862937130000711
8. a formulation comprising a composition according to any one of claims 1 to 7 and at least one solvent.
9. A formulation according to claim 8, wherein the composition and the solvent are formulated in the form of a solvent, and the solvent used is not particularly limited, and a halogenated saturated hydrocarbon solvent such as toluene, xylene, mesitylene, tetralin, decalin, bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane and the like, a halogenated unsaturated hydrocarbon solvent such as chlorobenzene, dichlorobenzene, trichlorobenzene and the like, an ether solvent such as tetrahydrofuran, tetrahydropyran and the like, an ester solvent such as alkyl benzoate and the like, which are well known to those skilled in the art can be used.
10. An organic electroluminescent device, comprising:
a first electrode;
a second electrode facing the first electrode;
the organic functional layer is clamped between the first electrode and the second electrode;
wherein the light-emitting layer comprises the composition of any one of claims 1 to 7.
11. The organic electroluminescent device according to claim 10, wherein the iridium metal complex and the organic compound are contained in a light-emitting layer, and wherein the iridium metal complex is present in an amount of 1 to 50% by mass.
12. A display or lighting device comprising the organic electroluminescent element according to any one of claims 10 to 11.
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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020038860A1 (en) * 2000-07-19 2002-04-04 Akira Tsuboyama Luminescence device
CN101153026A (en) * 2006-09-29 2008-04-02 株式会社半导体能源研究所 Quinoxaline derivative, and light emitting element, light emitting device, and electronic device using the quinoxaline derivative
CN101535324A (en) * 2006-07-28 2009-09-16 通用电气公司 Organic iridium compositions and their use in electronic devices
CN104744517A (en) * 2013-12-26 2015-07-01 财团法人工业技术研究院 Organic metal complex and organic electroluminescent device comprising the same
CN110654127A (en) * 2018-06-29 2020-01-07 住友化学株式会社 Method for producing film, method for producing organic EL element, and ink composition set for producing film
CN111777644A (en) * 2020-07-15 2020-10-16 奥来德(上海)光电材料科技有限公司 Organic iridium metal complex and preparation method and application thereof

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020038860A1 (en) * 2000-07-19 2002-04-04 Akira Tsuboyama Luminescence device
CN101535324A (en) * 2006-07-28 2009-09-16 通用电气公司 Organic iridium compositions and their use in electronic devices
CN101153026A (en) * 2006-09-29 2008-04-02 株式会社半导体能源研究所 Quinoxaline derivative, and light emitting element, light emitting device, and electronic device using the quinoxaline derivative
CN104744517A (en) * 2013-12-26 2015-07-01 财团法人工业技术研究院 Organic metal complex and organic electroluminescent device comprising the same
CN110654127A (en) * 2018-06-29 2020-01-07 住友化学株式会社 Method for producing film, method for producing organic EL element, and ink composition set for producing film
CN111777644A (en) * 2020-07-15 2020-10-16 奥来德(上海)光电材料科技有限公司 Organic iridium metal complex and preparation method and application thereof

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