CN113421982B - Host-guest composition and organic electroluminescent element comprising same - Google Patents

Host-guest composition and organic electroluminescent element comprising same Download PDF

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CN113421982B
CN113421982B CN202110642559.4A CN202110642559A CN113421982B CN 113421982 B CN113421982 B CN 113421982B CN 202110642559 A CN202110642559 A CN 202110642559A CN 113421982 B CN113421982 B CN 113421982B
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CN113421982A (en
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王子兴
郭建锋
张震
廖张程
吴空物
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Zhejiang Huadisplay Optoelectronics Co Ltd
University of Shanghai for Science and Technology
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Zhejiang Huadisplay Optoelectronics Co Ltd
University of Shanghai for Science and Technology
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Abstract

The invention belongs to the field of organic photoelectricity, and particularly relates to a host-guest composition which comprises an iridium metal complex and an organic compound, and an organic electroluminescent element using the composition as an organic functional layer. Wherein the structure of the organic compound is shown as the formula (I), and the structural formula (II) or the formula (III) of the iridium metal complex is shown as the formula (III):
Figure DDA0003108570060000011
organic compound the difference Δ ST between the singlet state energy level S1 and the triplet state energy level T1 of the compound represented by formula (I) is less than or equal to 0.35 electron volt; and iridium metal complexes of formula (II) or formula (III) and organic photovoltaic elements comprising the same may be understood by reference to the detailed description provided herein. The host-guest composition is applied to the luminescent layer of the organic electroluminescent diode, so that the current efficiency of a luminescent element is improved, the driving voltage is obviously reduced, the service life is prolonged, and the host-guest composition has good commercialization prospect.

Description

Host-guest composition and organic electroluminescent element comprising same
Technical Field
The invention belongs to the field of organic electroluminescence, and particularly relates to a host-guest composition of an organic compound and an iridium metal complex, 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 LCDs.
OLED light emission is divided into two types, fluorescence emission and phosphorescence emission, and it is theoretically assumed that the ratio of a singlet excited state to a triplet excited state due to charge binding is 1:3, and therefore, when a small molecular fluorescent material is used, the total energy available for light emission is only 25%, and the remaining 75% of the energy is lost due to a non-light emission mechanism of the triplet excited state, and thus the internal quantum efficiency limit of the fluorescent material is considered to be 25%. Professor Baldo and Forrest in 1998 found that triplet phosphorescence can be utilized at room temperature, and the upper limit of the original internal quantum efficiency is increased to 100%, and triplet phosphors are often heavy metal atoms and are formed of complexes, and by utilizing the heavy atom effect, the strong spin-orbit coupling effect causes the energy levels of the singlet excited state and the triplet excited state 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 increased.
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 greater than that of the guest material, i.e., 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 host-guest composition of an organic compound and an iridium metal complex and an organic electroluminescent element comprising the composition.
The present invention provides a host-guest composition of an iridium metal complex and an organic compound, such as
Formula (I):
Figure BDA0003108570040000021
in formula (I), X1 to X3 are independently selected from N or C-R4, and at least two are N; CY1 is an aromatic condensed ring or an aromatic hetero-condensed ring of C7-C30, Ar1 and Ar2 are independently selected from substituted or unsubstituted aryl of C6-C60 and substituted or unsubstituted heteroaryl of C1-C60; r1 to R5 are each independently selected from hydrogen, deuterium, CN, halogen, substituted or unsubstituted C1 to C60 alkyl, substituted or unsubstituted C2 to C60 alkenyl, substituted or unsubstituted C1 to C60 alkoxy, substituted or unsubstituted C1 to C60 cycloalkyl, substituted or unsubstituted C1 to C60 heteroalkyl, substituted or unsubstituted C6 to C60 aryl, substituted or unsubstituted C1 to C60 heteroaryl, substituted or unsubstituted C1 to C60 amine, substituted or unsubstituted C1 to C60 silicon, substituted or unsubstituted C6 to C60 aromatic fused ring, substituted or unsubstituted C1 to C60 heteroaromatic fused ring; ar1, Ar2, R1 through R5 each independently can be partially or fully deuterated, each independently can be partially or perfluorinated; r1 to R5 may be unsubstituted or polysubstituted according to valence bond rules; adjacent R1 to R5 may form a ring, and n is independently an integer of 0 to 8; and the difference between the singlet state energy level S1 and the triplet state energy level T1 of the organic compound is less than or equal to 0.35 electron volt;
The iridium metal complex is shown as a formula (II):
Figure BDA0003108570040000022
in formula (II) and formula (III), X is independently selected from NR17, NR18 or O, Y is C, ring CY2 is a C5-C60 carbocyclic group or a C1-C60 heterocyclic group, R, R6To R18Independently selected from hydrogen, deuterium, CN, F, C1-C60 alkyl, C1-C60 alkoxy, C1-C60 alkylsilyl, C1-C60 alkoxysilyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C1-C60 heteroaryl, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl ether groupAny one of substituted or unsubstituted aryl silicon base, substituted or unsubstituted heteroaryl silicon base and substituted or unsubstituted aryloxy silicon base; heterocyclyl means containing B, N, O, S, P (═ O), Si, and at least one heteroatom of P; n is an integer of 0 to 8, and when n is 2 or more, two or more R's are the same as or different from each other; all groups may be partially deuterated or fully deuterated.
Preferably, the iridium metal complex of the composition of the present invention is selected from one of the following structures, but represents no limitation thereto:
Figure BDA0003108570040000031
wherein, Y, CY2, R, R6To R18And n is the same as described above.
Preferably, the iridium metal complex of the composition of the present invention, wherein in the iridium metal complex of formula (II) or formula (III)
Figure BDA0003108570040000032
One selected from the following representative structures, but not representing a limitation thereto:
Figure BDA0003108570040000033
wherein, in formulas a (1) to a (6), Y is C, Y1 is O, S, N (R23), C (R23) (R24), Si (R23) (R24); y2 to Y4 are CR24 or N; r19 to R24, and R in claim 16To R18Denotes a binding site to Ir in formula (II) or formula (III) and denotes a binding site to the adjacent C in formula (II) or formula (III).
Preferably, the iridium metal complex of the composition of the present invention is of the formula (II) or (III)
Figure BDA0003108570040000041
At least one of R2, R3, R4, R5 and R6 is F, and the others are the same as above, but the invention is not limited thereto.
Preferably, the ring CY1 in the organic compound of formula (I) in the composition of the present invention is independently selected from one of formula (a) to formula (M), but does not represent a limitation thereto:
Figure BDA0003108570040000042
wherein Y is independently selected from O, S, N-R7, CR7R7, SiR7R7 and B-R7, and Z is independently N or C-R; r, R5 to R7 are each independently selected from hydrogen, deuterium, CN, F, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C1-C60 cycloalkyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C1-C60 heteroaryl, substituted or unsubstituted C1-C60 amine, substituted or unsubstituted C1-C60 silicon, substituted or unsubstituted C6-C60 aromatic fused ring, substituted or unsubstituted C1-C60 heteroaromatic fused ring; when two or more adjacent R5 to R7 may form a ring with each other; n is independently an integer from 0 to 8; m is 1 or 2; indicates the position of the linkage to N or C.
Preferably, the above formulae (a) to (M) are selected from one of the following representative structural formulae, but do not represent a limitation thereto:
Figure BDA0003108570040000051
wherein Y is independently selected from O, S, N-R7, CR7R7, SiR7R7 and B-R7, and Z is independently N or C-R; r, R6 to R8 are independently selected from CN, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C1-C60 cycloalkyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C1-C60 heteroaryl, substituted or unsubstituted C1-C60 amine, substituted or unsubstituted C1-C60 silicon, substituted or unsubstituted C6-C60 aromatic fused ring, substituted or unsubstituted C1-C60 heteroaromatic fused ring, and n is independently an integer of 0 to 8.
Preferably, the organic compound of formula (I) according to the invention is selected from one of the following representative structures, but not representing a limitation thereto:
Figure BDA0003108570040000061
wherein, X1 to X3 are independently selected from N or C-R4, and at least two are N; y is independently selected from one of O, S, N-R7, CR7R7, SiR7R7 and B-R7, and Z is independently N or C-R; ar1, Ar2, Ar R, R1 to R7, and n are as defined in claim 1.
Preferably, R1 to R24 in the organic compound and the iridium metal complex in the composition of the present invention are independently selected from hydrogen, deuterium, CN, and F, and may be independently selected from one of the following structures, but are not limited thereto:
Figure BDA0003108570040000071
Preferably, the organic compound of formula (I) of the composition of the present invention is selected from one of the following structures, but is not represented by the following limitations:
Figure BDA0003108570040000081
Figure BDA0003108570040000091
Figure BDA0003108570040000101
Figure BDA0003108570040000111
Figure BDA0003108570040000121
Figure BDA0003108570040000131
Figure BDA0003108570040000141
Figure BDA0003108570040000151
Figure BDA0003108570040000161
Figure BDA0003108570040000171
Figure BDA0003108570040000181
Figure BDA0003108570040000191
Figure BDA0003108570040000201
Figure BDA0003108570040000211
Figure BDA0003108570040000221
Figure BDA0003108570040000231
Figure BDA0003108570040000241
Figure BDA0003108570040000251
Figure BDA0003108570040000261
Figure BDA0003108570040000271
Figure BDA0003108570040000281
Figure BDA0003108570040000291
Figure BDA0003108570040000301
Figure BDA0003108570040000311
Figure BDA0003108570040000321
Figure BDA0003108570040000331
Figure BDA0003108570040000341
Figure BDA0003108570040000351
Figure BDA0003108570040000361
Figure BDA0003108570040000371
Figure BDA0003108570040000381
Figure BDA0003108570040000391
Figure BDA0003108570040000401
Figure BDA0003108570040000411
Figure BDA0003108570040000421
Figure BDA0003108570040000431
Figure BDA0003108570040000441
Figure BDA0003108570040000451
preferably, the iridium metal complex represented by formula (II) or formula (III) of the composition of the present invention is selected from one of the following structures, but is not represented by and limited to:
Figure BDA0003108570040000461
Figure BDA0003108570040000471
Figure BDA0003108570040000481
Figure BDA0003108570040000491
Figure BDA0003108570040000501
Figure BDA0003108570040000511
Figure BDA0003108570040000521
Figure BDA0003108570040000531
Figure BDA0003108570040000541
Figure BDA0003108570040000551
Figure BDA0003108570040000561
Figure BDA0003108570040000571
Figure BDA0003108570040000581
Figure BDA0003108570040000591
Figure BDA0003108570040000601
Figure BDA0003108570040000611
Figure BDA0003108570040000621
Figure BDA0003108570040000631
Figure BDA0003108570040000641
Figure BDA0003108570040000651
Figure BDA0003108570040000661
Figure BDA0003108570040000671
Figure BDA0003108570040000681
Figure BDA0003108570040000691
Figure BDA0003108570040000701
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 organic functional layer comprises one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer, and the composition is contained in at least the light emitting layer.
The mass percentage of the iridium metal complex in the formula (II) or the formula (III) 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 materials used for the organic electroluminescent element according to the present invention may be classified into top emission, low emission, or double-sided emission.
The compounds of the organic electroluminescent device according to the embodiment of the present invention can be applied to the aspects of 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, and the energy transmission between the organic compound and the iridium metal complex in the composition is more efficient, and the specific expression is that the current efficiency of an organic electroluminescent device manufactured by using the composition as a light-emitting layer is improved, the lighting voltage is reduced, and the operation life of the device is prolonged.
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 BDA0003108570040000721
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 not intended to limit the invention to, the following structures:
Figure BDA0003108570040000722
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 structure:
Figure BDA0003108570040000731
the organic compound represented by formula (I) in the present invention was obtained according to the synthesis method in CN 202110640090.0; the iridium metal complex represented by formula (II) is referred to CN 202011571779.4; obtained by a synthesis method of CN 202011571794.9.
The following table compares the energy level differences between RH-4 to RH-10 and N-11 to N-17-2, and is mainly characterized in that N-11 to N-17-2 have a lower Δ ST, which can convert triplet excitons into singlet excitons through intersystem crossing, thereby improving the utilization rate of the triplet excitons.
Compound (I) HOMO(eV) LUMO(eV) Triplet energy level T1(eV) ΔST(eV)
RH-5 -5.57 -2.83 2.33 0.46
RH-10 -5.58 -2.97 2.36 0.41
RH-4 -5.59 -2.95 2.36 0.47
N-11 -5.56 -3.00 2.36 0.14
N-15 -5.57 -2.99 2.37 0.18
N-15-2 -5.57 -2.99 2.37 0.18
N-17-2 -5.57 -2.99 2.36 0.14
N-15-3 -5.57 -3.05 2.34 0.12
N-110-3 -5.57 -3.07 2.33 0.11
N-15-4 -5.58 -3.03 2.34 0.11
Figure BDA0003108570040000732
Manufacturing of the OLED device:
in order to better illustrate the effects obtained by the present invention, the light-emitting layer of the present invention was constructed using iridium metal complexes RD-1 to RD-8 as guest materials and organic compounds N-11 to N-17-2 as host materials, and organic electroluminescent elements were prepared using RH-4 to RH-10 as reference hosts to illustrate the superiority of the overall properties of the composition of the present invention.
Figure BDA0003108570040000741
In the specific embodiment, the top-emitting OLED device is formed on ITO/Ag/ITO-containing glass, a hole injection layer is HT-1: P-3(97:3 v/v%), and the thickness is 10 nanometers; the hole transport layer is HT-1 and has a thickness of 100 nanometers; the electron blocking layer is HT-8 and is 10 nanometers thick, the light emitting layer is the composition of the invention, specifically (host material): (guest material) (97:3 v/v%) and is 35 nanometers thick, and the electron transport layer is ET-13: LiQ (50:50 v/v%) with a thickness of 35 nm, then evaporated with a cathode Yb of 1 nm, Ag of 14 nm and a 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
Figure BDA0003108570040000742
Figure BDA0003108570040000751
As can be seen from Table 1, in comparative devices 1-3, relatively good device results were obtained using the compound RH-5 as a reference host material, and comparative devices 4-10 constructed light-emitting layers of light-emitting elements using RH-5 as a host and RD-1 to RD-8 as guest materials. The replacement of RH-5 in the comparative devices with the compounds N-11 to N-17-2 of the present invention resulted in an improvement in the current efficiency of the devices of examples 1-28 and a significant improvement in the lifetime of the corresponding devices at the same operating voltage. Likewise, to achieve the same current efficiency, lower operating voltages can be achieved using the compositions of the present invention. Compared with the device example 2, the efficiency of the device 2 is improved by 10% and the service life is improved by 50 hours by comparing the device 2 with the device example 2. Meanwhile, different combinations of guest materials and host materials are selected, the obtained effects are also obviously different, compared with the case that the device 1 takes RD-1 as the guest material, RH-5 as the host material, in the case of the device 19, RD-5 as the guest material and N-15-3 as the host material, the new combination generates a remarkable gain effect, wherein the current efficiency is increased from 56.3cd/A to 67.7cd/A, and under the condition of increasing the efficiency of the device, the service life is also prolonged by 40 hours. The above results fully illustrate the significant advantages and commercial utility of the compositions provided by the present invention.
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 (19)

1. A host-guest composition comprising an organic compound and an iridium metal complex, wherein the organic compound is represented by formula (I):
Figure FDA0003562007960000011
in formula (I), X1 to X3 are independently selected from N or C-R4, and at least two are N; ar1 and Ar2 are independently selected from substituted or unsubstituted aryl of C6-C60 and substituted or unsubstituted heteroaryl of C1-C60; r1 to R5 are each independently selected from hydrogen, deuterium, CN, halogen, substituted or unsubstituted C1 to C60 alkyl, substituted or unsubstituted C2 to C60 alkenyl, substituted or unsubstituted C1 to C60 alkoxy, substituted or unsubstituted C1 to C60 cycloalkyl, substituted or unsubstituted C1 to C60 heteroalkyl, substituted or unsubstituted C6 to C60 aryl, substituted or unsubstituted C1 to C60 heteroaryl, substituted or unsubstituted C1 to C60 amine, substituted or unsubstituted C1 to C60 silicon, substituted or unsubstituted C6 to C60 aromatic fused ring, substituted or unsubstituted C1 to C60 heteroaromatic fused ring; ar1, Ar2, R1 to R5 each independently may be partially or fully deuterated, each independently may be partially or perfluorinated; r1 to R5 may be unsubstituted or polysubstituted according to valence bond rules; adjacent R1 to R5 may form a ring, n is independently an integer of 0 to 8; and the difference between the singlet state energy level S1 and the triplet state energy level T1 of the organic compound is less than or equal to 0.35 electron volt;
Wherein ring CY1 is selected from one of formulas (a) through (M):
Figure FDA0003562007960000021
y is independently selected from one of O, S, N-R7, CR7R7, SiR7R7 and B-R7, and Z is independently N or C-R; r, R5 to R7 are each independently selected from hydrogen, deuterium, CN, F, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C1-C60 cycloalkyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C1-C60 heteroaryl, substituted or unsubstituted C1-C60 amine, substituted or unsubstituted C1-C60 silicon, substituted or unsubstituted C6-C60 aromatic fused ring, substituted or unsubstituted C1-C60 heteroaromatic fused ring; when two or more adjacent R5 to R7 may form a ring with each other; n is independently an integer from 0 to 8; m is 1 or 2; indicates the position of the linkage to N or C;
the iridium metal complex is shown as a formula (II) or a formula (III):
Figure FDA0003562007960000022
in formula (II) and formula (III), X is independently selected from NR17, NR18 or O, Y is C, ring CY2 is a C5-C60 carbocyclic group or a C1-C60 heterocyclic group, R, R6To R18Independently selected from any one of hydrogen, deuterium, CN, F, C1-C60 alkyl, C1-C60 alkoxy, C1-C60 alkylsilyl, C1-C60 alkoxysilyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C1-C60 heteroaryl, substituted or unsubstituted arylether group, substituted or unsubstituted heteroaryl ether group, substituted or unsubstituted arylsilyl, substituted or unsubstituted heteroarylsilyl, and substituted or unsubstituted aryloxysilyl; heterocyclyl means containing B, N, O, S, P (═ O), Si, and at least one heteroatom of P; n is an integer of 0 to 8, and when n is 2 or more, two or more R's are the same as or different from each other; all groups may be partially deuterated or fully deuterated.
2. The composition as claimed in claim 1, wherein the iridium metal complex of formula (II) is selected from one of the following representative structural formulae:
Figure FDA0003562007960000031
wherein Y, CY2, R, R6To R18And n is as defined in claim 1.
3. The composition as claimed in any one of claims 1 or 2, wherein in the iridium metal complex of formula (II) or formula (III)
Figure FDA0003562007960000032
Selected from the following representative structuresOne of which is:
Figure FDA0003562007960000033
wherein, in formulas a (1) to a (6), Y is C, Y1 is O, S, N (R23), C (R23) (R24), Si (R23) (R24); y2 to Y4 are CR24 or N; r19 to R24, and R in claim 16To R18Denotes a binding site to Ir in formula (II) or formula (III) and denotes a binding site to the adjacent C in formula (II) or formula (III).
4. The composition as claimed in claim 1 or 2, wherein the iridium metal complex is of formula (II) or (III)
Figure FDA0003562007960000041
At least one of R2, R3, R4, R5 and R6 is F, the others being as defined in claim 1.
5. The composition of claim 1, wherein CY1 in the organic compound of formula (I) is independently selected from one of the following representative structural formulae:
Figure FDA0003562007960000042
wherein Y is independently selected from O, S, N-R7, CR7R7, SiR7R7 and B-R7, and Z is independently N or C-R; r, R6 to R8 are independently selected from CN, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C1-C60 cycloalkyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C1-C60 heteroaryl, substituted or unsubstituted C1-C60 amine, substituted or unsubstituted C1-C60 silicon, substituted or unsubstituted C6-C60 aromatic fused ring, substituted or unsubstituted C1-C60 heteroaromatic fused ring, and n is independently an integer of 0 to 8.
6. The composition according to claim 1, wherein the organic compound of formula (I) is selected from one of the following representative structures:
Figure FDA0003562007960000051
wherein, X1 to X3 are independently selected from N or C-R4, and at least two are N; y is independently selected from one of O, S, N-R7, CR7R7, SiR7R7 and B-R7, and Z is independently N or C-R; ar1, Ar2, R, R1 to R7, n are as defined in claim 1.
7. The composition of claim 1 or 2, wherein R1 through R24 are independently selected from hydrogen, deuterium, CN, F, or one of the following structures:
Figure FDA0003562007960000061
8. the composition according to claim 1 or 2, wherein the organic compound of formula (I) is selected from one of the following representative structures:
Figure FDA0003562007960000071
Figure FDA0003562007960000081
Figure FDA0003562007960000091
Figure FDA0003562007960000101
Figure FDA0003562007960000111
Figure FDA0003562007960000121
Figure FDA0003562007960000131
Figure FDA0003562007960000141
Figure FDA0003562007960000151
Figure FDA0003562007960000161
Figure FDA0003562007960000171
Figure FDA0003562007960000181
Figure FDA0003562007960000191
Figure FDA0003562007960000201
Figure FDA0003562007960000211
Figure FDA0003562007960000221
Figure FDA0003562007960000231
Figure FDA0003562007960000241
Figure FDA0003562007960000251
Figure FDA0003562007960000261
Figure FDA0003562007960000271
Figure FDA0003562007960000281
Figure FDA0003562007960000291
Figure FDA0003562007960000301
Figure FDA0003562007960000311
Figure FDA0003562007960000321
Figure FDA0003562007960000331
Figure FDA0003562007960000341
Figure FDA0003562007960000351
Figure FDA0003562007960000361
Figure FDA0003562007960000371
Figure FDA0003562007960000381
Figure FDA0003562007960000391
Figure FDA0003562007960000401
Figure FDA0003562007960000411
Figure FDA0003562007960000421
Figure FDA0003562007960000431
Figure FDA0003562007960000441
9. the composition of claim 1 or 2, wherein the iridium metal complex of formula (II) or formula (III) is selected from one of the following representative structures:
Figure FDA0003562007960000451
Figure FDA0003562007960000461
Figure FDA0003562007960000471
Figure FDA0003562007960000481
Figure FDA0003562007960000491
Figure FDA0003562007960000501
Figure FDA0003562007960000511
Figure FDA0003562007960000521
Figure FDA0003562007960000531
Figure FDA0003562007960000541
Figure FDA0003562007960000551
Figure FDA0003562007960000561
Figure FDA0003562007960000571
Figure FDA0003562007960000581
Figure FDA0003562007960000591
Figure FDA0003562007960000601
Figure FDA0003562007960000611
Figure FDA0003562007960000621
Figure FDA0003562007960000631
Figure FDA0003562007960000641
Figure FDA0003562007960000651
Figure FDA0003562007960000661
Figure FDA0003562007960000671
Figure FDA0003562007960000681
Figure FDA0003562007960000691
10. a formulation characterized in that it comprises a composition according to claim 1 or 2 and at least one solvent.
11. The formulation of claim 10, wherein the solvent is an unsaturated hydrocarbon solvent, a halogenated saturated hydrocarbon solvent, a halogenated unsaturated hydrocarbon solvent, an ether solvent, or an ester solvent.
12. A formulation as claimed in claim 11 wherein said unsaturated hydrocarbon solvent is toluene, xylene, mesitylene, tetralin, decahydronaphthalene, bicyclohexane, n-butylbenzene, sec-butylbenzene or tert-butylbenzene.
13. The formulation of claim 11, wherein the halogenated saturated hydrocarbon solvent is carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane or bromocyclohexane.
14. A formulation as claimed in claim 11 wherein the halogenated unsaturated hydrocarbon solvent is chlorobenzene, dichlorobenzene or trichlorobenzene.
15. The formulation of claim 11, wherein the ether solvent is tetrahydrofuran or tetrahydropyran.
16. The formulation of claim 11, wherein the ester solvent is an alkyl benzoate.
17. 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 organic functional layer comprises one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and the composition of any one of claims 1 to 9 is contained at least in the light emitting layer.
18. The organic electroluminescent device as claimed in claim 17, wherein the percentage by mass of the iridium metal complex in the composition of the light-emitting layer is 1 to 50%.
19. A display or lighting device comprising the organic electroluminescent element according to any one of claims 17 to 18.
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CN112614964A (en) * 2020-12-27 2021-04-06 浙江华显光电科技有限公司 Composition and organic electroluminescent element comprising same
CN112670426A (en) * 2020-12-27 2021-04-16 浙江华显光电科技有限公司 Composition and organic electroluminescent element comprising same
CN112679550A (en) * 2020-12-27 2021-04-20 浙江华显光电科技有限公司 Iridium metal complex and organic photoelectric element using same

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CN110698387A (en) * 2019-09-04 2020-01-17 宁波卢米蓝新材料有限公司 Fused ring compound and preparation method and application thereof
CN112614964A (en) * 2020-12-27 2021-04-06 浙江华显光电科技有限公司 Composition and organic electroluminescent element comprising same
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