CN113161498A - Organic compound composition, organic electroluminescent element containing organic compound composition and application of organic electroluminescent element - Google Patents

Organic compound composition, organic electroluminescent element containing organic compound composition and application of organic electroluminescent element Download PDF

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CN113161498A
CN113161498A CN202110218784.5A CN202110218784A CN113161498A CN 113161498 A CN113161498 A CN 113161498A CN 202110218784 A CN202110218784 A CN 202110218784A CN 113161498 A CN113161498 A CN 113161498A
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王志盛
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Shanghai Lancheng Photoelectric Technology Co ltd
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Abstract

The invention provides an organic compound composition, an organic electroluminescent element containing the same and application of the organic compound composition and the organic electroluminescent element. The present invention provides a novel combination of organic compounds, and provides a composition which has more efficient injection and transport of holes and electrons, and good electron/hole balance in a light-emitting layer. The organic compound with relatively low triplet state energy level is used for obtaining high-efficiency and high-energy level deep blue luminescence, and the glass transition temperature of the material is high, so that a high-efficiency device containing the composition can be applied to the fields of display, illumination, backlight source and the like, and has a commercial application prospect.

Description

Organic compound composition, organic electroluminescent element containing organic compound composition and application of organic electroluminescent element
Technical Field
The invention belongs to the technical field of organic photoelectricity, and particularly relates to an organic compound composition, an organic electroluminescent element containing the organic compound composition and application of the organic electroluminescent element and the organic electroluminescent element.
Background
Among organic optoelectronic devices, especially organic electroluminescent diodes (OLEDs) are gradually entering the field of vision of people as a new generation of flat panel display technology, and their wide application prospects and the recent technological leap make OLEDs one of the most popular researches in the field of flat panel information display and the development of scientific research products. In recent 25 years, Organic Light Emitting Diodes (OLEDs) have become a research hotspot in the field of flat panel displays internationally due to their advantages of self-luminescence, wide viewing angle, low operating voltage, fast response time, flexibility, etc., and commercial products have begun to be applied in the fields of flat panel displays and lighting. The development of the OLED technology in the field of display and illumination is always limited by the efficiency and the service life of the blue OLED, and the high-efficiency blue OLED can obviously improve the display reality and reduce the power consumption of display and illumination devices. The current blue OLED technology for displays such as mobile phones is still mainly based on fluorescent material, but its external quantum efficiency is low (less than 12.5% when no light is taken out). It has been reported that a thermally activated delayed fluorescent material capable of realizing pure blue light (<465 nm) or deep blue light (<440 nm), an OLED device in which a host and the thermally activated delayed fluorescent material are taken as a sensitizer as a common host, generally emits sky blue light with an emission peak above 468 nm, and a pure blue or deep blue OLED with high efficiency and long lifetime has not been realized yet. The literature reports that materials capable of realizing pure blue or deep blue OLEDs have the problems of low triplet state energy level (ET), low glass transition temperature (Tg), and the like to different extents, which lead to the problems of low efficiency, high operating voltage, short lifetime, and the like of corresponding OLED devices, and the requirements of commercial applications cannot be met at present. The invention makes further research on the basis of the prior patent CN108963099B, provides a novel combination mode of organic compounds, obtains a composition with more effective and balanced hole and electron injection and transmission, can obtain high-efficiency deep blue light emission by using the composition, obviously improves the luminous efficiency of OLED, reduces the operating voltage, and has commercial application prospect.
Disclosure of Invention
In order to solve the problems of low current efficiency and poor performance in the prior blue OLED technology, the present invention provides a composition for an organic electroluminescent element, the composition comprising at least one or more compounds represented by formula I and formula II:
formula I is shown below:
Figure BDA0002953553330000021
wherein Z1 to Z3 in formula I are independently selected from N or C-L2-R2, A is independently selected from
Figure BDA0002953553330000022
Y is N or C-R3; l1, L2 are independently selected from a single bond, substituted or unsubstituted arylene group of C6-C20, substituted or unsubstituted heterocyclic group of C2-C20, or a combination thereof, R1 to R3 are independently selected from hydrogen, deuterium, CN, halogen, substituted or unsubstituted alkyl group of C1-C60, substituted or unsubstituted alkenyl group of C2-C60, substituted or unsubstituted alkoxy group of C1-C60, substituted or unsubstituted cycloalkyl group of C1-C60, substituted or unsubstituted heteroalkyl group of C1-C60, substituted or unsubstituted aryl group of C6-C60, substituted or unsubstituted heteroaryl group of C1-C60, substituted or unsubstituted amino group of C1-C60, substituted or unsubstituted fused ring silicon group of C1-60, substituted or unsubstituted aromatic group of C6-C60, substituted or unsubstituted heteroaromatic group of C1-C60;
formula II is shown below:
Figure BDA0002953553330000023
wherein Y1 to Y6 of formula II are independently selected from N or one of C-L4-R4, at least two of Y1 to Y6 are N; l4 is independently selected from a single bond, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C2-C20 heterocyclic group, or a combination thereof; r4 is independently selected from hydrogen, deuterium, CN, halogen, substituted or unsubstituted C1-C60 alkyl, 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 silicon base, substituted or unsubstituted C6-C60 aromatic fused ring, substituted or unsubstituted C1-C60 heteroaromatic fused ring; when two or more of adjacent R4 s are present, they may form a ring with each other; r1 to R4 each independently may be partially or fully deuterated, each independently may be partially or perfluorinated in formula I or II; r1 to R4 may be unsubstituted or polysubstituted according to valence bond rules; in particular, the triplet energy level of the compound of formula I or formula II is not less than 2.68eV, and the glass transition temperature is greater than 105 degrees, so as to meet the requirements of commercial applications.
The present invention claims compositions of organic compounds, wherein each of the above R1 through R4 is independently selected from one of the following structures, but not limited thereto:
Figure BDA0002953553330000031
wherein Y and ring a are the same as above and X is independently selected from absent, or O, S, N-R5, B-R5, P-R5, O ═ P-R5, C-R5R6, C ═ O, S ═ O, S (═ O)2Or one of Si-R5R 6; r5 and R6 are as defined above for R1.
In the composition of the present invention, formula I is selected from one of the formulae represented by H-1 to H-41, but represents not limited thereto:
Figure BDA0002953553330000032
wherein Y is C-R3 or N;
the chemical formula II is selected from one of the structures represented by E-1 or E-2, but does not represent any limitation thereto:
Figure BDA0002953553330000033
wherein L4, R1 to R4 are as defined for R1 above;
preferably, R1 to R4 are independently selected from one of the following structures, but do not represent a limitation thereto:
Figure BDA0002953553330000041
the chemical formula I in the composition is selected from any one of H-1 to H-41, and R1 to R3 are independently substituted by the S-1 to S-73 to form one of the following representative structural formulas, but not limited to:
Figure BDA0002953553330000051
Figure BDA0002953553330000061
Figure BDA0002953553330000071
Figure BDA0002953553330000081
Figure BDA0002953553330000091
Figure BDA0002953553330000101
Figure BDA0002953553330000111
Figure BDA0002953553330000121
Figure BDA0002953553330000131
Figure BDA0002953553330000141
Figure BDA0002953553330000151
Figure BDA0002953553330000161
Figure BDA0002953553330000171
Figure BDA0002953553330000181
Figure BDA0002953553330000191
Figure BDA0002953553330000201
Figure BDA0002953553330000211
Figure BDA0002953553330000221
Figure BDA0002953553330000231
Figure BDA0002953553330000241
the composition of the present invention has the chemical formula II selected from
Figure BDA0002953553330000251
R11 to R3 are independently substituted with S-1 to S-78 to form one of the following representative structural formulas, but not represent a limitation:
Figure BDA0002953553330000252
Figure BDA0002953553330000261
Figure BDA0002953553330000271
Figure BDA0002953553330000281
Figure BDA0002953553330000291
Figure BDA0002953553330000301
Figure BDA0002953553330000311
Figure BDA0002953553330000321
Figure BDA0002953553330000331
Figure BDA0002953553330000341
Figure BDA0002953553330000351
Figure BDA0002953553330000361
Figure BDA0002953553330000371
Figure BDA0002953553330000381
Figure BDA0002953553330000391
Figure BDA0002953553330000401
the invention claims a formulation comprising the said composition of organic compounds and at least one solvent, the solvent is not limited at all, and unsaturated hydrocarbon solvents such as toluene, xylene, mesitylene, tetralin, decalin, bicyclohexyl, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane and the like, halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, trichlorobenzene and the like, ether solvents such as tetrahydrofuran, tetrahydropyran and the like, ester solvents such as alkyl benzoate and the like, which are well known to those skilled in the art can be used.
The present invention also claims an organic light emitting 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 a composition of the above organic compounds.
Preferably, the combination ratio of formula I to formula II is I: and II is 1: 0.25-4, and a corresponding luminous layer is constructed.
Preferably, the organic electroluminescent element has a light emission peak between 390 nm and 455 nm.
In a practical embodiment of the invention, the compounds of the formulae I and II can be combined with fluorescent or phosphorescent compounds in the light-emitting layer, the fluorescent or phosphorescent compounds preferably being composed of organic compounds or organometallic complexes or known and unknown light-emitting materials in the case of inorganic fluorescent materials.
When the composition of the invention is used as an energy donor and an organic electroluminescent device constructed by luminescent materials, the luminous peak can be adjusted along with the luminescent materials, and the luminous wavelength is between 405 nanometers and 750 nanometers.
In the present invention, the organic photoelectric device is an anode which can be formed by depositing a metal or an oxide having conductivity and an alloy thereof on a substrate by a sputtering method, electron beam evaporation, vacuum evaporation, 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. Except the above method, the organic electroluminescent device is prepared by vapor deposition of the cathode, the organic layer and the anode on the substrate in this order.
The organic electroluminescent device of the present invention may be classified into top emission, low emission, or double-sided emission. The compound of the organic electroluminescent device according to the embodiment of the invention can be applied to electroluminescent devices such as lighting OLED, flexible OLED, organic photoreceptor, organic thin film transistor and the like.
The compound provided by the invention is obtained after further research according to a patent CN108963099B, compared with the technology in CN108963099B, the compound provided by the invention can have a lower triplet state energy level, but has better hole transmission capability or electron transmission capability, the element has lower operation voltage and higher efficiency by taking the composition provided by the invention as a light-emitting layer, the external quantum efficiency is greatly improved (by 23-38% compared with the result in CN 108963099B), particularly under the same light-emitting peak, the external quantum efficiency is close to 16%, and a deep blue OLED device with the external quantum efficiency of 20% can be expected to be obtained through later-stage device structure and material matching adjustment, so that the commercial application of the deep blue OLED is realized.
Drawings
FIG. 1 is a structural layer diagram of an OLED 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.
FIG. 2 is a J-V curve for a single hole device of compound H-1-7 and compound D1-3-1 of the present invention.
FIG. 3 is a J-V curve of a single electron device of the present invention of compound E-1-77 and compound P4-3-29
Fig. 4 is an EL spectrum of device 10 of the present invention.
Detailed Description
In order to make the technical solutions of the present application better understood, the technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the drawings in the embodiments of the present application, and it is obvious that the described embodiments are only a part of the embodiments of the present application, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present application.
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 BDA0002953553330000421
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 of the following structure:
Figure BDA0002953553330000431
the compound of formula I of the present invention is used as a hole transport material in a hole transport layer, a hole injection layer or an exciton blocking layer, and the compound of formula I may be used alone or may be formed together with one or more p-type dopants as described above.
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 is not limited thereto:
Figure BDA0002953553330000432
the compound of formula II of the present invention can be used as an electron transport layer. The electron transport layer may be formed by combining the above compounds with one or more n-type dopants (e.g., LiQ).
Preferably, the examples were device verified with a composition constructed with one of the following representative compounds, obtained according to literature methods:
Figure BDA0002953553330000441
general method for manufacturing organic light-emitting element:
a P-doped material P-1-P-6 or the P-doped material and a hole transport material are jointly formed into a Hole Injection Layer (HIL) with the thickness of 5-50nm by a vacuum evaporation, spin coating, printing or printing method on the surface of ITO glass with the light-emitting area of 2mm multiplied by 2mm, then a Hole Transport Layer (HTL) with the thickness of 5-200nm is formed, then a light-emitting layer (EML) with the thickness of 10-100nm is formed on the hole transport layer, finally an Electron Transport Layer (ETL) with the thickness of 10-200nm and a cathode with the thickness of 50-200nm are sequentially formed, 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, thereby manufacturing the organic light-emitting element.
OLED device examples:
the structure of the bottom-emitting OLED device is specifically implemented on ITO-containing glass, the HIL is HT-1: P-3(97:3 v/v%), and the thickness is 10 nanometers; HTL is HT-1, and the thickness is 75 nanometers; EBL is a compound H-1-22 with the thickness of 10-20 nm, EML is the composition with the thickness of 20-35 nm, and HBL is a compound represented by the chemical formula II or ET-11 with the thickness of 10 nm; ETL is ET-1-77: LiQ (50:50 v/v%) with the thickness of 25-35 nm, and then evaporating a cathode Yb of 1 nm and Al of 40 nm.
Example 1: the evaporation rate of the organic material under high vacuum is 0.5-5%/s, and the structure is ITO/HT-1: P-3(97:3 v/v%) (10)/HT-1(75)/H-1-22(20)/H-1-7: E-1-92(1:1 v/v%) (20)/ET-11 (10)/ET-1-77: LiQ (50:50 v/v%) (25)/Yb (1)/Al (40) (device 1) in which the materials of the layers are separated by "/", and the thickness of each layer is shown in parentheses and expressed in nanometers. The current density-voltage-luminance curves were measured using a Keithley2400 current meter and a PR650 spectrometer.
Example 2: an OLED device (device 2) was prepared by replacing H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with H-1-7: E-1-92(4:6 v/v%) (20) under high vacuum.
Example 3: an OLED device (device 3) was prepared by replacing H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with H-1-22: E-1-92(4:6 v/v%) (20) under high vacuum.
Example 4: an OLED device (device 4) was prepared by replacing H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with H-1-94: E-1-92(4:6 v/v%) (20) under high vacuum.
Example 5: an OLED device (device 5) was prepared by replacing H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with H-1-496: E-1-92(4:6 v/v%) (20) under high vacuum.
Example 6: an OLED device (device 6) was prepared by replacing H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with H-1-496: E-1-92(4.5:5.5 v/v%) (20) under high vacuum.
Example 7: an OLED device (device 7) was prepared by replacing H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with H-1-7: E-1-92(1:1 v/v%) (20) under high vacuum.
Example 8: an OLED device (device 8) was prepared by replacing H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with H-21-10: E-1-92(4:6 v/v%) (20) under high vacuum.
Example 9: an OLED device (device 9) was prepared by replacing H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with H-21-22: E-1-92(4:6 v/v%) (20) under high vacuum.
Example 10: an OLED device (device 10) was prepared by replacing H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with H-36-10: E-1-92(4:6 v/v%) (20) under high vacuum.
Example 11: an OLED device (device 11) was prepared by replacing H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with H-12-7: E-1-77(1:1 v/v%) (20) under high vacuum.
Example 12: an OLED device (device 12) was prepared by replacing H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with H-1-7: E-1-77(4.5:5.5 v/v%) (20) under high vacuum.
Example 13: an OLED device (device 13) was prepared by replacing H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with H-1-94: E-1-77(4.5:5.5 v/v%) (20) under high vacuum.
Example 14: an OLED device (device 14) was prepared by replacing H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with H-1-7: E-1-1403(4.5:5.5 v/v%) (20) under high vacuum.
Example 15: an OLED device (device 14) was prepared by replacing H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with H-1-7: E-2-1403(4.5:5.5 v/v%) (20) under high vacuum.
Example 16: an OLED device (device 16) was prepared by replacing H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with H-1-7: E-1-155(4.5:5.5 v/v%) (20) under high vacuum.
Example 17: an OLED device (device 17) was prepared under high vacuum by replacing H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with H-1-7: E-1-155: Firpic (42:52:6 v/v%) (20).
Example 18: OLED device (device 18) was prepared under high vacuum by replacing H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with H-1-7: E-1-155: Ir (ppy)2acac (41:51:8 v/v%) (20).
Comparative device 1: an OLED device (comparative device 1) was prepared under high vacuum by replacing H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with D1-3-1: P4-3-29(4:6 v/v%) (20) in patent CN 108963099B.
Comparative device 2: an OLED device (comparative device 2) was prepared under high vacuum by replacing H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with D1-3-1: P4-3-29(1:1 v/v%) (20) in patent CN 108963099B.
Comparative device 3: an OLED device (comparative device 3) was prepared under high vacuum by replacing the H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with the D1-3-1: E-1-155(4:6 v/v%) (20) in patent CN 108963099B.
Comparative device 4: an OLED device (comparative device 4) was prepared under high vacuum by replacing H-1-7: E-1-92(1:1 v/v%) (20) in example 1 with H-1-7: P4-3-29(4:6 v/v%) (20) in patent CN 108963099B.
The OLEDs were characterized by standard methods.
Figure BDA0002953553330000471
As can be seen from FIG. 2, the representative compound H-1-7 in the structural formula I of the invention has better single hole transport effect and lower hole injection barrier than D1-3-1 in patent CN 108963099B; the representative compound E-1-77 in the structural formula II has better single electron transmission effect and lower electron injection barrier than P4-3-29 in patent CN108963099B (figure 3). The ternary composition provided by the invention adopts different proportions of the components to construct the light-emitting layer of the OLED device, can obtain the deep blue OLED with the maximum external quantum efficiency of 15.8%, and has lower starting voltage. Due to the improvement of the injection and transmission efficiency of the holes and the electrons, more holes and electrons are balanced in the light-emitting layer, the number of excitons for forming light emission is increased, and the OLED device with higher brightness and efficiency is obtained. In comparison with comparative device 1 and comparative device 3, an increase in efficiency was obtained by replacing P4-3-29 with only the representative compound of formula II of the present invention, E-1-155. The use of E-1-155 allows more electron-hole pairs to be obtained in the light-emitting layer, which can improve the light-emitting efficiency.
The device 1 to the device 16 of the embodiments of the present invention adopt different combination schemes and composition ratios, and the device results are shown in Table 1. from the comparison in Table 1, it can be seen that H-1-7: E-1-92(1:1 v/v%) (20 nm) in the device 1 and the combination D1-3-1: P4-3-29(1:1 v/v%) in the patent CN108963099B in the comparison device 2 are adopted, the starting voltage is reduced by 0.1V, and particularly the light emitting brightness is reduced from 4800cd/m2Is increased to 6000cd/m2(ii) a Further, the ratio of H-1-7: E-1-92 is adjusted to 4:6, and then the brightness of the device 2 is improved to 6500cd/m2And the starting voltage is further reduced to 2.9 volts, the external quantum efficiency EQE of the OLED reaches 15.1 percent, the starting voltage of the comparison device 1 is 3.2 volts, the EQE is only 11.4 percent, and the efficiency of the device 2 is improved by 32 percent on the basis. The external quantum efficiencies of the devices were compared as the peak positions of the luminescence for each composition were different. By adjusting the combination ratio of the compositions obtained by adopting different compounds represented by structural formula I and structural formula II, the device 10 obtains a deep blue device with the external quantum efficiency of 15.8 percent and the light-emitting peak at 440 nanometers, which is 138 percent of the external quantum efficiency of 11.7 percent of the device 3, and the operating voltage is reduced to 2.9 volts. Particularly, H-1-7: E-2-1403 in the device 15 is 45:55, and the deep blue OLED device with the light-emitting peak of 418 nanometers and the EQE of 15.2 percent is obtained. Even the worse case of the present invention, the EQE of device 1 is 123% of that of comparative device 3. The above results fully illustrate that lower turn-on voltage, higher efficiency blue OLEDs can be obtained using the compositions of the present invention. Carrying out detailed chemical structure research and device structure research, innovatively finding out specific composition and specific combination proportion to obtain a device with better comprehensive performance. In particular, the invention uses the conventional fluorescent compound with lower triplet state energy level to obtain the deep blue light OLED device ( devices 2,7,8,11,12,14,15 and 16) with the external quantum efficiency close to 16 percent, so that the deep blue light OLED device provides possibility for expanding new application in the fields of display, illumination, backlight source, medical health and the like.
While embodiments of the present invention have been described in detail, other embodiments of the present invention will be apparent to those skilled in the art from consideration of the specification and practice of the invention disclosed herein. This application is intended to cover any variations, uses, or adaptations of the invention following, in general, the principles of the application and including such departures from the present disclosure as come within known or customary practice within the art to which the invention pertains. It is intended that the specification and examples be considered as exemplary only, with a true scope and spirit of the application being indicated by the following claims.
It will be understood that the present application is not limited to the precise arrangements described above and shown in the drawings and that various modifications and changes may be made without departing from the scope thereof. The scope of the application is limited only by the appended claims. The above description is only exemplary of the present application and should not be taken as limiting the present application, as any modification, equivalent replacement, or improvement made within the spirit and principle of the present application should be included in the protection scope of the present application.

Claims (12)

1. A composition of organic compounds, the composition comprising compounds represented by formula I and formula II, formula I being shown below:
Figure 1
in formula I, Z1-Z3 are independently selected from N or C-L2-R2, and ring A is independently selected from
Figure FDA0002953553320000012
Y is N or C-R3; l1 and L2 are independently selected from single bond, substituted orUnsubstituted arylene of C6-C20, substituted or unsubstituted C2-C20 heterocyclic group, or a combination thereof, R1 to R3 are independently selected from hydrogen, deuterium, CN, halogen, substituted or unsubstituted alkyl of C1-C60, substituted or unsubstituted alkenyl of C2-C60, substituted or unsubstituted alkoxy of C1-C60, substituted or unsubstituted cycloalkyl of C1-C60, substituted or unsubstituted heteroalkyl of C1-C60, substituted or unsubstituted aryl of C6-C60, substituted or unsubstituted heteroaryl of C1-C60, substituted or unsubstituted amine of C1-C60, substituted or unsubstituted C1-C60, silicon base, substituted or unsubstituted aromatic fused ring of C6-C60, substituted or unsubstituted heteroaromatic fused ring of C1-C60;
formula II is shown below:
Figure 2
in the formula II, Y1-Y6 are independently selected from N or one of C-L4-R4, and at least two of Y1-Y6 are N; l4 is independently selected from a single bond, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C2-C20 heterocyclic group, or a combination thereof; r4 is independently selected from hydrogen, deuterium, CN, halogen, substituted or unsubstituted C1-C60 alkyl, 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 silicon base, substituted or unsubstituted C6-C60 aromatic fused ring, substituted or unsubstituted C1-C60 heteroaromatic fused ring; when two or more of adjacent R4 s are present, they may form a ring with each other; r1 to R4 each independently may be partially or fully deuterated, each independently may be partially or perfluorinated in formula I or II; r1 to R4 may be unsubstituted or polysubstituted according to valence bond rules; and the triplet energy level of the organic compound selected from the chemical formulas I and II is not lower than 2.68 eV; the glass transition temperature is greater than 105 degrees.
2. The composition of organic compounds according to claim 1, characterized in that R1 to R4 are each independently selected from one of the following structures:
Figure FDA0002953553320000021
wherein Y and ring a are the same as in claim 1, X is independently selected from absent, or from O, S, N-R5, B-R5, P-R5, O-P-R5, C-R5R6, C-O, S-O, S (═ O)2Or one of Si-R5R 6; r5 and R6 are as defined for R1 in claim 1.
3. The composition according to any one of claims 1 to 2, wherein formula I in the composition is selected from one of the structures represented by H-1 to H-41:
Figure FDA0002953553320000022
wherein Y is C-R4 or N;
formula II is selected from one of the structures represented by E-1 or E-2:
Figure FDA0002953553320000023
wherein L4, R1 to R4 are as defined in claim 1.
4. The composition of claim 1, wherein R1 through R4 are independently selected from one of the following structures:
Figure FDA0002953553320000031
5. the composition of claim 1, wherein formula I is selected from any one of H-1 to H-41, and is independently substituted with S-1 to S-73 to form one of the following representative structural formulas:
Figure FDA0002953553320000041
Figure FDA0002953553320000051
Figure FDA0002953553320000061
Figure FDA0002953553320000071
Figure FDA0002953553320000081
Figure FDA0002953553320000091
Figure FDA0002953553320000101
Figure FDA0002953553320000111
Figure FDA0002953553320000121
Figure FDA0002953553320000131
Figure FDA0002953553320000141
Figure FDA0002953553320000151
Figure FDA0002953553320000161
Figure FDA0002953553320000171
Figure FDA0002953553320000181
Figure FDA0002953553320000191
Figure FDA0002953553320000201
Figure FDA0002953553320000211
Figure FDA0002953553320000221
Figure FDA0002953553320000231
the composition has a chemical formula II selected from
Figure FDA0002953553320000241
(ii) one of the following representative structural formulae formed by independent substitution of S-1 to S-78:
Figure FDA0002953553320000242
Figure FDA0002953553320000251
Figure FDA0002953553320000261
Figure FDA0002953553320000271
Figure FDA0002953553320000281
Figure FDA0002953553320000291
Figure FDA0002953553320000301
Figure FDA0002953553320000311
Figure FDA0002953553320000321
Figure FDA0002953553320000331
Figure FDA0002953553320000341
Figure FDA0002953553320000351
Figure FDA0002953553320000361
Figure FDA0002953553320000371
Figure FDA0002953553320000381
Figure FDA0002953553320000391
6. the composition of claim 1, wherein the composition has a combined ratio of formula I to formula II of I: and II is 1: 0.25-4.
7. A formulation comprising the composition of any one of claims 1 to 6 and at least one solvent, the solvent used is not particularly limited, and unsaturated hydrocarbon solvents such as toluene, xylene, mesitylene, tetrahydronaphthalene, decahydronaphthalene, bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, etc. known to those skilled in the art can be used; halogenated saturated hydrocarbon solvents such as chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane and bromocyclohexane; halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, trichlorobenzene and the like; ether solvents such as tetrahydrofuran and tetrahydropyran; and ester solvents such as alkyl benzoate.
8. An organic light-emitting 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 a composition of organic compounds according to any one of claims 1 to 6.
9. The organic light-emitting device according to claim 8, wherein the light-emitting layer of the organic functional layer is formed by combining the composition with a light-emitting material comprising an organometallic complex, an organic compound, or an inorganic fluorescent material.
10. The organic light-emitting device according to claim 8, wherein the organic light-emitting device has a light emission peak between 390 nm and 455 nm.
11. The organic light-emitting device according to claim 8, wherein the organic light-emitting device has a light emission peak between 405 nm and 750 nm.
12. A display or lighting device comprising the organic light-emitting device according to any one of claims 8 to 11.
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US20150380662A1 (en) * 2014-06-30 2015-12-31 Samsung Display Co., Ltd. Organic light-emitting device
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