CN110759850A - Compound and application thereof - Google Patents
Compound and application thereof Download PDFInfo
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- CN110759850A CN110759850A CN201810832798.4A CN201810832798A CN110759850A CN 110759850 A CN110759850 A CN 110759850A CN 201810832798 A CN201810832798 A CN 201810832798A CN 110759850 A CN110759850 A CN 110759850A
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Abstract
The invention provides a novel compound and application thereof, wherein the compound is shown as the following formula (1-1):
wherein: y is1‑Y4Each is independently selected from N or C; y is5‑Y16Each independently selected from N, CH or CR; x is selected from O, S, NR or CR 'R', the R, R 'and R' are each independently selected from C1‑C10Alkyl, substituted or unsubstituted C6‑C30Aryl, substituted or unsubstituted C3‑C30One of heterocyclic aryl; r1、R2And R3Each independently selected from H, C1‑C10Alkyl, substituted or unsubstituted C6‑C30Aryl, substituted or unsubstituted C3‑C30One of heterocyclic aryl; m, n and p are each independently selected from integers of 0 to 4; a and B are independently selected from H and are not H at the same time, or A and B represent a group which is connected with the mother nucleus in a ring-combining way, and the groups are respectively and independently selected from C6‑C30Aryl or C3‑C30A heterocyclic aryl group. The compound of the present invention shows excellent device performance and stability when used as a light emitting material in an OLED device. The invention also protects the organic compounds adopting the compounds with the general formulaAn electroluminescent device.
Description
Technical Field
The present invention relates to a novel compound of the general formula, and more particularly, to an organic compound which can be used as a host material for a light-emitting layer of an organic electroluminescent device, and an organic electroluminescent device using the same.
Background
The organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages of self-luminescence, low-voltage direct current drive, full curing, wide viewing angle, light weight, simple composition and process and the like, and compared with the liquid crystal display, the organic electroluminescent display does not need a backlight source, has large viewing angle, low power, 1000 times of response speed of the liquid crystal display, and lower manufacturing cost than the liquid crystal display with the same resolution, so the organic electroluminescent device has wide application prospect.
With the continuous advance of the OLED technology in the two fields of illumination and display, people pay more attention to the research of efficient organic materials affecting the performance of OLED devices, and an organic electroluminescent device with good efficiency and long service life is generally the result of the optimized matching of the device structure and various organic materials. In the most common OLED device structures, the following classes of organic materials are typically included: hole injection materials, hole transport materials, electron transport materials, and light emitting materials (dyes or doped guest materials) and corresponding host materials of each color. The phosphorescent host materials used at present have single carrier transport capability, such as hole-based transport hosts and electron-based transport hosts. The single carrier transport ability causes mismatching of electrons and holes in the light emitting layer, resulting in severe roll-off of efficiency and shortened lifetime. At present, in the use process of a phosphorescent host, a bipolar material or a double-host material matching mode is adopted to solve the problem of unbalanced carriers of a single-host material. The bipolar material realizes the common transmission of electrons and holes in one compound, and the molecular structure is more complex; the double-main-body material is used for realizing the transmission and combination of electrons and holes in the luminous layer by matching two materials, wherein one material is used as an electron type material, the other material is used as a hole type material, the electrons and the holes are combined at an interface after being conducted by the two materials, the two materials have wider sources, and the better device performance can be realized by adopting a combination mode of different materials.
Disclosure of Invention
The invention aims to solve the problems of weak electron transport capability and unbalanced carrier transport in the prior art, provides a novel general formula compound with good electron transport capability, and simultaneously provides an organic electroluminescent device adopting the novel compound.
The invention provides a compound of general formula (I), which has structural formulas shown as the following formulas (1-1) to (1-9):
wherein, Y1-Y4Each is independently selected from N or C; y is5-Y16Each independently selected from N, CH or CR;
x is selected from O, S, NR or CR 'R', the R, R 'and R' are each independently selected from C1-C10Alkyl, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C3-C30One of heterocyclic aryl;
R1、R2and R3Each independently selected from H, C1-C10Alkyl, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C3-C30One of heterocyclic aryl; r1、R2And R3Each independently can be connected with the connected mother core structure to form a ring;
m, n and p are each independently selected from integers of 0 to 4;
in particular, when m is 2, 3 or 4, any two adjacent R are1May together form a ring structure with the carbon atoms to which they are bonded; when n is 2, 3 or 4, any two adjacent R2May together form a ring structure with the carbon atoms to which they are bonded; when p is 2, 3 or 4, any two adjacent R3May together form a ring structure together with the carbon atom to which they are bonded, and the above-formed ring structure may be a cycloalkyl structure, an aryl structure or a heteroaryl structure.
A and B each independently represent a group which is attached to the mother nucleus in a ring-merging manner, and each of the groups is independently selected from C6-C30Aryl or C3-C30One of heterocyclic aryl, or A and B are independently selectedFrom H and not simultaneously H; the connection site of the mother nucleus and A or B to form a ring is C atom.
When R, R', R "and R are as described above1、R2、R3When the substituent groups are respectively and independently selected from substituted aryl or heterocyclic aryl, the substituent groups are respectively and independently selected from halogen and C1-C10Alkyl or cycloalkyl of, C2-C10Alkenyl radical, C1-C6Alkoxy or thioalkoxy group of (C)6-C30Monocyclic aromatic hydrocarbon or condensed ring aromatic hydrocarbon group of (A), C3-C30One of the monocyclic heteroaromatic group or the condensed ring heteroaromatic group of (a).
In particular, when defining the above R1、R2、R3And A, B, each independently selected from aryl, are meant to be selected from aromatic ring systems having a certain number of ring backbone carbon atoms, including monocyclic ring structure substituents such as phenyl and the like, as well as aromatic ring substituents of covalently linked structures such as biphenyl, terphenyl and the like.
In particular, when defining the above R1、R2、R3And A, B when each is independently selected from heterocyclic aryl groups means a monocyclic or fused ring aryl group containing one or more heteroatoms selected from B, N, O, S, P (═ O), Si and P and having ring carbon atoms.
Further, the above-mentioned general formulae (1-1) to (1-9) each independently may preferably be the following general formulae (2-1) to (2-10):
in the above formulae (2-1) to (2-10), Y1-Y16、X、R1、R2、R3And m, n and p are each as defined in the general formulae (1-1) to (1-9), A and B are the same or different and are each independently selected from C6-C30Aryl or C3-C30A heterocyclic aryl group.
Further, in the formula (2-4), Y1-Y4At least one of which is N and A and B are not both H.
In the formula (2-5), Y1-Y8At least one of them is N, Y9-Y12At least one of which is N.
In the formula (2-6), Y5-Y8And Y13-Y16At least one of them is N, Y9-Y12At least one of which is N.
In the formula (2-7), Y9-Y12At least one of which is N.
In the formula (2-10), Y1-Y4At least one of which is N and A and B are not both H.
Still further, the compounds represented by the general formulae (1-1) to (1-9) of the present invention may preferably be compounds of the following specific structures: A1-A70, these compounds being representative only.
The invention also provides, as another aspect thereof, the use of a compound as described above in an organic electroluminescent device. The compounds of the invention are preferably used as light-emitting host materials in organic electroluminescent devices.
As still another aspect of the present invention, the present invention also provides an organic electroluminescent device comprising a first electrode, a second electrode, and a plurality of organic layers interposed between the first electrode and the second electrode, the organic layers containing therein compounds represented by the following general formulae (1-1) to (1-9):
in the general formulae (1-1) to (1-9): y is1-Y4Each is independently selected from N or C; y is5-Y16Each independently selected from N, CH or CR;
x is selected from O, S, NR or CR 'R', the R, R 'and R' are each independently selected from C1-C10Alkyl, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C3-C30One of heterocyclic aryl;
R1、R2and R3Each independently selected from H, C1-C10Alkyl, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C3-C30One of heterocyclic aryl; r1、R2And R3Each independently can be connected with the connected mother core structure to form a ring;
m, n and p are each independently selected from integers of 0 to 4;
a and B each independently represent a group which is attached to the mother nucleus in a ring-merging manner, and each of the groups is independently selected from C6-C30Aryl or C3-C30One of heterocyclic aryl, or A and B are independently selected from H and are not H at the same time; the connection site of the mother nucleus and A or B to form a ring is C atom.
When R, R', R "and R are as described above1、R2、R3When the substituent groups are respectively and independently selected from substituted aryl or heterocyclic aryl, the substituent groups are respectively and independently selected from halogen and C1-C10Alkyl or cycloalkyl of, C2-C10Alkenyl radical, C1-C6Alkoxy or thioalkoxy group of (C)6-C30Monocyclic aromatic hydrocarbon or condensed ring aromatic hydrocarbon group of (A), C3-C30One of the monocyclic heteroaromatic group or the condensed ring heteroaromatic group of (a).
Further, the compounds of the general formulae (1-1) to (1-9) contained in the organic layer in the above-described organic electroluminescent device of the present invention may preferably be compounds of the following general formulae (2-1) to (2-10), independently of each other:
in the above formulae (2-1) to (2-10), Y1-Y16、X、R1、R2、R3And m, n and p are each as defined in the general formulae (1-1) to (1-9), A and B are the same or different and are each independently selected from C6-C30Aryl or C3-C30A heterocyclic aryl group.
Further, in the formula (2-4), Y1-Y4At least one of which is N and A and B are not both H.
In the formula (2-5), Y1-Y8At least one of them is N, Y9-Y12At least one of which is N.
In the formula (2-6), Y5-Y8And Y13-Y16At least one of them is N, Y9-Y12At least one of which is N.
In the formula (2-7), Y9-Y12At least one of which is N.
In the formula (2-10), Y1-Y4At least one of which is N and A and B are not both H.
The research shows that the compound with the general formula has good film-forming property and is suitable for being used as a luminescent main material and an electron transmission material. The principle is not clear, and it is assumed that the following reasons may be: in the compounds represented by the general formulas (1-1) to (1-9), the parent structure of the triphenylene condensed aromatic ring with polycyclic conjugated characteristics is introduced into the molecular skeleton, and the bond energy between atoms is high, so that the compounds have good thermal stability, are beneficial to solid-state accumulation between molecules and prolong the service life of the materials. The compound has a larger conjugated system, ensures that the triplet state energy level of the system can be effectively reduced, can improve the transmission efficiency of charges, can improve the luminous efficiency of a host material, and particularly shows that the luminous efficiency and the service life of the host material can be improved.
In particular, the compounds of the general formulae (1-1) to (1-9) may be used as, but not limited to, a light emitting layer material in an organic electroluminescent device.
In addition, the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Detailed Description
The present invention will be described in further detail below with reference to specific embodiments in order to make the present invention better understood by those skilled in the art.
Compounds of synthetic methods not mentioned in the present invention are all starting products obtained commercially. Solvents and reagents used in the present invention, such as methylene chloride, petroleum ether, ethanol, tetrahydrofuran, N-dimethylacetamide, anhydrous magnesium sulfate, carbazole, benzimidazole and the like, can be purchased from domestic chemical product markets, such as reagents from national drug group, TCI, shanghai Bidi medicine, carbofuran, and the like. In addition, they can be synthesized by a known method by those skilled in the art.
The analytical testing of intermediates and compounds in the present invention uses an abciex mass spectrometer (4000QTRAP) and a siemens analyzer.
The synthesis of the compounds of the present invention is briefly described below.
Representative synthetic route:
representative synthetic route 1:
different target compounds can be obtained by changing boric acid of different A, B rings and dibenzo heterocycles. It should be noted that the above synthesis methods are mainly applied to C-C coupling and C-N coupling, but the methods are not limited to this coupling method, and those skilled in the art may select other methods, but the methods are not limited to these methods, and all methods may be selected as needed.
More specifically, the following gives synthetic methods of representative compounds of the present invention.
Synthesis example 1: synthesis of Compound A1
To a reaction flask were added 35.4g (100mmol) of o-bromoiodobenzene, 22.5g (110mmol) of 1-naphthoic acid, 0.9g (0.785mmol, 0.5%) of tetrakis (triphenylphosphine palladium), 1500ml of toluene, 1000ml of ethanol, 43.3g (314mmol) of potassium carbonate/1000 ml of water, and reacted at 80 ℃ for 3.5 hours. And stopping the reaction after the reaction is finished. Cooled to room temperature, filtered and the resulting solid purified by recrystallization from toluene to give M1 as a white powder.
Dissolving 27.2g (100mmol) of 2-bromo-9, 9-dimethylfluorene and 21.1g (100mmol) of 1-carbazole boric acid in xylene, adding cuprous iodide, 1, 10-phenanthroline and potassium phosphate, heating and refluxing, reacting for 12 hours, washing with water, concentrating, and performing column chromatography to obtain an M2 intermediate.
Into a reaction flask were charged M121.8g (100mmol), M216.5g (110mmol), tetrakis (triphenylphosphine palladium) 0.9g (0.785mmol, 0.5%), toluene 1500ml, ethanol 1000ml, potassium carbonate 43.3g (314 mmol)/water 1000ml, and reacted at 80 ℃ for 3.5 hours. And stopping the reaction after the reaction is finished. Cooled to room temperature, filtered and the resulting solid purified by recrystallization from toluene to give M3.
Dissolving M3 in DMF, adding ferric trichloride, introducing oxygen, and stirring at normal temperature for 48 h. Extracting the reaction liquid with ethyl acetate, concentrating the organic phase, and carrying out column chromatography to obtain a product A1.
1H NMR(CDCl3,400MHz)8.95(d,J＝12.0Hz,3H),8.55(s,1H),8.33(s,1H),8.17(s,1H),8.10(d,J＝8.0Hz,2H),8.04(s,1H),7.90(s,1H),7.81(s,2H),7.68–7.44(m,6H),7.34(s,1H),7.24(s,1H),7.13(d,J＝10.0Hz,2H),1.69(s,6H).
Synthesis example 2:
28.1g (100mmol) of o-bromoiodobenzene, 23.8g (110mmol) of 3-phenanthreneboronic acid, 0.9g (0.785mmol, 0.5%) of tetrakis (triphenylphosphine palladium), 1500ml of toluene, 1000ml of ethanol, 43.3g (314mmol) of potassium carbonate/1000 ml of water were added to a reaction flask, and the reaction was carried out at 80 ℃ for 3.5 hours. And stopping the reaction after the reaction is finished. Cooled to room temperature, filtered and the resulting solid purified by recrystallization from toluene to give M1 as a white powder.
Dissolving 38.1g (100mmol) of 2- (4-bromophenyl) -4, 6-diphenyl triazine and 21.1g (100mmol) of 1-carbazole boric acid in xylene, adding cuprous iodide, 1, 10-phenanthroline and potassium phosphate, heating and refluxing, reacting for 12 hours, washing with water, concentrating, and performing column chromatography to obtain an M2 intermediate.
To a reaction flask were added M133.2g (100mmol), M256.9g (110mmol), 0.9g (0.785mmol, 0.5%) of tetrakis (triphenylphosphine palladium), 1500ml of toluene, 1000ml of ethanol, 43.3g (314mmol) of potassium carbonate/1000 ml of water, and the reaction was carried out at 80 ℃ for 3.5 hours. And stopping the reaction after the reaction is finished. Cooled to room temperature, filtered and the resulting solid purified by recrystallization from toluene to give M3.
Dissolving M3 in DMF, adding ferric trichloride, introducing oxygen, and stirring at normal temperature for 48 h. Extracting the reaction liquid with ethyl acetate, concentrating the organic phase, and carrying out column chromatography to obtain a product A7.
1H NMR(CDCl3,400MHz)9.16(s,1H),8.98(s,1H),8.85(s,1H),8.54(d,J＝12.0Hz,2H),8.36(s,4H),8.27(s,1H),8.11(s,1H),8.00–7.83(m,6H),7.81(s,1H),7.78–7.52(m,6H),7.50(s,6H),7.13(d,J＝10.0Hz,2H).
Synthesis example 3:
28.1g (100mmol) of o-bromoiodobenzene, 23.1g (110mmol) of 3-carbazolboronic acid, 0.9g (0.785mmol, 0.5%) of tetrakis (triphenylphosphine palladium), 1500ml of toluene, 1000ml of ethanol, 43.3g (314mmol) of potassium carbonate/1000 ml of water are added into a reaction flask, and the reaction is carried out at 80 ℃ for 3.5 h. And stopping the reaction after the reaction is finished. Cooled to room temperature, filtered and the resulting solid purified by recrystallization from toluene to give M1 as a white powder.
In a reaction flask, 24g (100mmol) of 2-chloro-3-phenylquinoxaline, M132 g (100mmol), DMF200ml, 43.3g (314mmol) of potassium carbonate were added, and the reaction was carried out at 120 ℃ for 8 hours. And stopping the reaction after the reaction is finished. After cooling to room temperature, water was added to the reaction solution, and the mixture was filtered, and the obtained solid was purified by recrystallization from toluene to obtain M2.
Dissolving 20g (100mmol) of iodobenzene and 21.1g (100mmol) of 1-carbazole boric acid in xylene, adding cuprous iodide, 1, 10-phenanthroline and potassium phosphate, heating and refluxing, reacting for 12h, washing with water, concentrating, and performing column chromatography to obtain an M3 intermediate.
In a reaction flask, M252.5g (100mmol), M330.5g (110mmol), 0.9g (0.785mmol, 0.5%) of tetrakis (triphenylphosphine palladium), 1500ml of toluene, 1000ml of ethanol, 43.3g (314mmol) of potassium carbonate/1000 ml of water were charged, and the reaction was carried out at 80 ℃ for 3.5 hours. And stopping the reaction after the reaction is finished. Cooled to room temperature, filtered and the resulting solid purified by recrystallization from toluene to give M4.
Dissolving M4 in DMF, adding ferric trichloride, introducing oxygen, and stirring at normal temperature for 48 h. Extracting the reaction liquid with ethyl acetate, concentrating the organic phase, and carrying out column chromatography to obtain a product A28.
1H NMR(CDCl3,400MHz)8.98(s,1H),8.79(s,1H),8.55(s,2H),8.40(s,2H),8.27(s,1H),8.11(s,2H),7.81(d,J＝4.0Hz,3H),7.74–7.42(m,14H),7.13(d,J＝10.0Hz,4H).
Device embodiments
Detailed description of the preferred embodiments
The organic light emitting diode comprises a first electrode and a second electrode which are arranged on a substrate, and an organic material arranged between the electrodes, wherein a hole transport layer, a light emitting layer and an electron transport layer are arranged between the first electrode and the second electrode.
As the substrate, a substrate for an organic light emitting display is used, for example: glass, polymer materials, glass with TFT components, polymer materials, and the like.
The first electrode can be Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), or tin dioxide (SnO)2) Transparent conductive materials such as zinc oxide (ZnO), metal materials such as silver and its alloys, aluminum and its alloys, organic conductive materials such as PEDOT, and multilayer structures of these materials. The second electrode can be selected from, but not limited to, metals, metal mixtures, oxides, such as magnesium silver mixtures, LiF/Al, ITO, and the like.
The hole transport layer may be, but is not limited to, a combination of one or more of HT1-HT31 listed below.
The red phosphorescent host may be, but is not limited to, a combination of one or more of RH1-RH31 listed below.
The red phosphorescent dopant may be, but is not limited to, a combination of one or more of RPD1-RPD29 listed below.
The electron transport layer may be, but is not limited to, one or a combination of more of ET1-ET57 listed below.
An electron injection layer may also be included in the device between the electron transport layer and the second electrode, the electron injection layer material including, but not limited to, combinations of one or more of the following.
LiQ,LiF,NaCl,CsF,Li2O,Cs2CO3,BaO,Na,Li,Ca。
The preparation process of the organic electroluminescent device in the embodiment is as follows:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the first electrode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, vacuum evaporating HT-11 on the first electrode layer film to form a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
evaporating HT-5 on the hole injection layer in vacuum to serve as a hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 80 nm;
the light-emitting layer of the device is vacuum evaporated on the hole transport layer, the light-emitting layer comprises a host material and a dye material, the evaporation rate of the host material is adjusted to be 0.1nm/s by using a multi-source co-evaporation method, the evaporation rate proportion of the dye is set to be 3% or 5%, the total evaporation film thickness is 30nm, and the specific host material and the specific dye are described in the device structure of each embodiment.
Vacuum evaporating an electron transport layer material ET42 of the device on the light-emitting layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 30 nm;
LiF with the thickness of 0.5nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 150nm is used as a second electrode of the device.
The following OLED devices of the various examples were prepared according to the above procedure, specifically the device in each example having the following structure:
comparative example 1:
ITO(150nm)/HT-11(10nm)/HT-5(80nm)/R-1:3％RPD-2(30nm)/ET42(30nm)/LiF(0.5nm)/Al(150nm)
example 1:
ITO(150nm)/HT-11(10nm)/HT-5(80nm)/A8:3％RPD-2(30nm)/ET42(30nm)/LiF(0.5nm)/Al(150nm)
example 2:
ITO(150nm)/HT-11(10nm)/HT-5(80nm)/A27:3％RPD-2(30nm)/ET42(30nm)/LiF(0.5nm)/Al(150nm)
example 3:
ITO(150nm)/HT-11(10nm)/HT-5(80nm)/A37:3％RPD-2(30nm)/ET42(30nm)/LiF(0.5nm)/Al(150nm)
example 4:
ITO(150nm)/HT-11(10nm)/HT-5(80nm)/A43:3％RPD-2(30nm)/ET42(30nm)/LiF(0.5nm)/Al(150nm)
comparative example 2:
ITO(150nm)/HT-11(10nm)/HT-5(80nm)/RH-16:50％R-2:3％RPD-2(30nm)/ET42(30nm)/LiF(0.5nm)/Al(150nm)
example 5:
ITO(150nm)/HT-11(10nm)/HT-5(80nm)/RH-16:50％A1:3％RPD-2(30nm)/ET42(30nm)/LiF(0.5nm)/Al(150nm)
example 6:
ITO(150nm)/HT-11(10nm)/HT-5(80nm)/RH-16:50％A25:3％RPD-2(30nm)/ET42(30nm)/LiF(0.5nm)/Al(150nm)
example 7:
ITO(150nm)/HT-11(10nm)/HT-5(80nm)/RH-16:50％A33:3％RPD-2(30nm)/ET42(30nm)/LiF(0.5nm)/Al(150nm)
example 8:
ITO(150nm)/HT-11(10nm)/HT-5(80nm)/RH-16:50％A54:3％RPD-2(30nm)/ET42(30nm)/LiF(0.5nm)/Al(150nm)
the organic electroluminescent device prepared by the above process was subjected to the following performance measurement:
the driving voltage and current efficiency of the organic electroluminescent devices prepared in examples and comparative examples and the lifetime of the devices were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 5000cd/m2The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency; the life test of LT95 is as follows: using a luminance meter at 5000cd/m2The luminance drop of the organic electroluminescent device was measured to be 4750cd/m by maintaining a constant current at luminance2Time in hours.
The properties of the organic electroluminescent device prepared by the above specific examples are detailed in the following table.
Table 1:
from the data in table 1 above, it can be seen that:
as can be seen from a comparison of examples 1-4 with comparative example 1, the current efficiency of the synthesized compounds of the present invention is higher than that of devices prepared using prior art materials when used as a light emitting host material in OLED devices, while the voltage and lifetime properties are also advantageous.
As can be seen from the comparison between examples 5-8 and comparative example 2, when the compound of the present invention is used in combination with a phosphorescent host material as a dual host material, the current efficiency of the device prepared is also much higher than that of the device prepared by using a material of the prior art as a luminescent dual host material, and the voltage and lifetime performance are also significantly superior.
The results show that the novel organic material is used for the organic electroluminescent device, can effectively reduce the take-off and landing voltage, improve the current efficiency and prolong the service life of the device, and is a luminescent material with good performance.
Although the invention has been described in connection with the embodiments, the invention is not limited to the embodiments described above, and it should be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the invention, and the scope of the invention is outlined by the appended claims.
Claims (8)
1. A compound of the general formula (1-1) to (1-9) below:
in formulae (1-1) to (1-9): y is1-Y4Each is independently selected from N or C; y is5-Y16Each independently selected from N, CH or CR;
x is selected from O, S, NR or CR' R "; the R, R 'and R' are independently selected from C1-C10Alkyl, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C3-C30One of heterocyclic aryl;
R1、R2and R3Each independently selected from H, C1-C10Alkyl, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C3-C30One of heterocyclic aryl; r1、R2And R3Each independently can be connected with the connected mother core structure to form a ring;
m, n and p are each independently selected from integers of 0 to 4;
a and B each independently represent a group which is attached to the mother nucleus in a ring-merging manner, and each of the groups is independently selected from C6-C30Aryl or C3-C30One of heterocyclic aryl, or A and B are respectively independently selected from H and are differentWhen the value is H;
when the above groups have substituents, the substituents are respectively and independently selected from halogen and C1-C10Alkyl or cycloalkyl of, C2-C10Alkenyl radical, C1-C6Alkoxy or thioalkoxy group of (C)6-C30Monocyclic aromatic hydrocarbon or condensed ring aromatic hydrocarbon group of (A), C3-C30One of the monocyclic heteroaromatic group or the condensed ring heteroaromatic group of (a).
2. The compound of general formula (la) according to claim 1, wherein formulae (1-1) to (1-9) are each independently represented by any one of the following formulae (2-1) to (2-10):
in the above formulae (2-1) to (2-10), Y1-Y16、X、R1、R2、R3And m, n and p are each as defined in the general formulae (1-1) to (1-9), A and B are the same or different and are each independently selected from C6-C30Aryl or C3-C30A heterocyclic aryl group.
3. A compound of formula (la) according to claim 2, wherein:
in the formula (2-4), Y1-Y4At least one of which is N, and A and B are not both H;
in the formula (2-5), Y1-Y8At least one of them is N, Y9-Y12At least one of which is N;
in the formula (2-6), Y5-Y8And Y13-Y16At least one of them is N, Y9-Y12At least one of which is N;
in the formula (2-7), Y9-Y12At least one of which is N;
in the formula (2-10), Y1-Y4At least one of which is N and A and B are not both H.
4. A compound of formula (la) according to claim 1 or 2, selected from the compounds of the following specific structures:
5. use of a compound of general formula (la) according to claim 1 or 2 as a light-emitting host material in an organic electroluminescent device.
6. The use of the structural compound according to claim 4 as a light-emitting host material in an organic electroluminescent device.
7. An organic electroluminescent device comprising a first electrode, a second electrode and one or more organic layers interposed between said first and second electrodes, characterized in that said organic layers comprise at least one compound of formula (la) according to any one of claims 1 or 2.
8. The organic electroluminescent device according to claim 7, wherein the compound of the formula included in the organic layer is selected from compounds of the following specific structures:
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