CN108727389B - Pyrene derivative and application thereof in organic luminescent material - Google Patents
Pyrene derivative and application thereof in organic luminescent material Download PDFInfo
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Abstract
The invention discloses a pyrene derivative and application thereof in an organic light-emitting material, and also provides an organic electroluminescent device which comprises the organic electroluminescent compound. The pyrene structure is introduced into the compound, so that the efficient and balanced transmission performance of current carriers is realized.
Description
Technical Field
The invention relates to a novel pyrene derivative organic compound, in particular to a compound for an organic electroluminescent device and application of the compound in the organic electroluminescent device.
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. TADF excellent in light emission properties has attracted general attention in recent years. TADF is main body time wareThe main body T1 of the piece will go back to its S1 by RISC process and then go through the long range
Energy delivery delivers light to the object, unlike conventional host energy delivery via short range Dexter. The more efficient exciton transfer in devices with TADF as the host is one of the reasons for the superior device performance. More efficient exciton transfer allows the device doping concentration to be reduced, while achieving high efficiency, low roll off efficiency and long lifetime for green devices at low doping concentrations. The conventional fluorescent dye emits light by relaxation from a singlet state to a ground state after receiving energy transfer of a host material, but the light emission efficiency is low because singlet excitons occupy only 25% of the proportion. The TADF material can realize reverse gap crossing and improve the utilization rate of excitons due to the extremely small energy difference between the triplet state and the singlet state. The search for suitable TADF materials has been a continuing effort in the art.
In addition, it remains a challenge in the art to develop new guest materials (i.e., luminescent dyes) for light-emitting layers, to improve energy utilization efficiency and to achieve high light-emitting efficiency.
Disclosure of Invention
In order to overcome the problems of the conventional host materials and guest materials in the above prior art, the present invention provides a novel class of compounds for organic electroluminescent devices. The compound is easy to realize thermal excitation delayed fluorescence by introducing a novel pyrene derivative structure, realizes the efficient and balanced transmission performance of current carriers, and can be used as a host material and a guest material for an organic electroluminescent device. The compounds of the present invention are represented by the following general formula (I).
Wherein:
indicates the site of attachment,
l is a bond, -O-, -S-, -NRa-、C1-C5Alkylene group of (C)1-C3Alkylene) -O- (C)1-C3Alkylene group), C6-C12Arylene of, C3-C12The heteroarylene group of (a);
R1selected from hydrogen, substituted or unsubstituted C1～C12Alkyl, halogen, cyano, nitro, hydroxy, silyl, C6～C30Substituted or unsubstituted aromatic hydrocarbon group (preferably substituted or unsubstituted C)6-C12Aromatic hydrocarbon group of (2), C3～C30Substituted or unsubstituted heteroaryl (preferably substituted or unsubstituted C)3-C12Heteroaryl of (a); r3、R4、R5、R6、R7、R8Independently selected from hydrogen, substituted or unsubstituted C1～C12Alkyl, halogen, cyano, nitro, hydroxy, silyl, C6～C30Substituted or unsubstituted aromatic hydrocarbon group (preferably substituted or unsubstituted C)6-C12Aromatic hydrocarbon group of (2), C10～C30Substituted or unsubstituted heteroaryl (preferably substituted or unsubstituted C)4-C12Heteroaryl of (a); or adjacent R4、R6、R7Or R8The two carbon atoms to which they are attached form a 5-membered, 6-membered ring;
x is C (R)b)2、NRcO, S; n is equal to 0, 1;
m, r, p, q, s and t are independently 0,1 or 2; when R is 2, two R3The same or different; when m is 2, two R4The same or different; when p is 2, two R5The same or different; when q is 2, two R6The same or different; when s is 2, two R7The same or different; when t is 2, two R8The same or different, and the like,
Ra、Rband RcIndependently selected from hydrogen, C1-C5Alkylene, halogen, cyano, nitro, hydroxy of (a); two RbThe same or different.
In a preferred embodiment of the present invention, the substituent on the pyrene structure bonded to Ar is an axisymmetric structure.
In another preferred embodiment of the present invention, said R is7With R in symmetrical position8Are the same substituents.
In a preferred embodiment of the present invention, L is a bond, a substituted or unsubstituted phenylene group.
Preferably, the aromatic hydrocarbon groups are independently selected from phenyl, phenyl substituted with furyl, thienyl, pyrrolyl and/or pyridyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof, fluoranthryl, triphenylene, pyrenyl, perylenyl, perylene, and the like,
At least one of a phenyl group and a tetracenyl group. More preferably, the biphenyl group includes 2-biphenyl, 3-biphenyl, and 4-biphenyl groups, and the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, and m-terphenyl-2-yl groups; the naphthyl is 1-naphthyl and/or 2-naphthyl; the anthracene group includes at least one of a 1-anthracene group, a 2-anthracene group, and a 9-anthracene group; the fluorenyl group comprises at least one of 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group and 9-fluorenyl group; the fluorenyl derivative comprises at least one of 9,9 '-dialkyl fluorene, 9, 9' -spirobifluorene and indenofluorene; the pyrenyl group comprises at least one of 1-pyrenyl group, 2-pyrenyl group and 4-pyrenyl group; the tetracenyl group includes at least one of 1-tetracenyl group, 2-tetracenyl group, and 9-tetracenyl group.
According to the present invention, the above heteroaryl group means a monocyclic or fused ring aromatic group having at least one heteroatom comprising one or more heteroatoms selected from B, N, O, S, P (═ O), Si and P, preferably said heteroatom comprises one or more heteroatoms selected from O, S and N, and having a number of ring backbone atoms; wherein Ar mentioned above is each independently C3-C90Substituted or unsubstituted heteroaryl, meaning that the heteroaryl may have 3 to 90 backbone carbon atoms, preferably, Ar is each independentlyGround is C5-C30Substituted or unsubstituted heteroaryl, meaning that the heteroaryl has 5 to 30 skeletal carbon atoms.
Preferably, the heteroaryl is independently selected from at least one of furyl, phenylfuryl, thienyl, phenylthienyl, pyrrolyl, phenylpyrrolyl, pyridyl, phenylpyridyl, pyrazinyl, fluorenyl, indenofluorenyl, quinoline, triazinyl, benzofuryl, benzothienyl, benzotriazine, benzopyrazinyl, isobenzofuryl, indolyl, benzoquinoline, dibenzofuryl, dibenzothienyl, dibenzopyrrolyl, carbazolyl and derivatives thereof, phenyl-substituted diazoles, phenanthrolinyl, phenanthrolinothiazolyl and benzodioxolyl, wherein the carbazolyl derivatives may include, but are not limited to, at least one of 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole, and indolocarbazole.
Specifically, R in the above general formula (I)1、R3、R4、R5、R6、R7、R8、Ra、Rb、RcIndependently selected from H, C1～C6Alkyl, Cl, Br, CN or Si (CH)3)3。
Further, in the general formula (I) of the present invention, when R is1、R3、R4、R5、R6、R7、R8、Ra、Rb、RcEach independently selected from alkyl groups, preferred alkyl groups include: methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl.
In the present invention, Ca-CbThe expression (b) represents that the group has the number of carbon atoms of a to b, and generally the number of carbon atoms does not include the number of carbon atoms of the substituent unless otherwise specified.
In the present invention, the expression of chemical elements includes the concept of chemically identical isotopes, such as the expression of "hydrogen", and also includes the concept of chemically identical "deuterium" and "tritium".
The heteroatom in the present invention generally refers to an atom or an atomic group selected from B, N, O, S, P, P (═ O), Si, and Se.
In the present invention, when the defined group is a substituted group, it is preferred that the substituents on said substituted group include, but are not limited to, halogen, nitro, cyano, C1-C6Alkyl or C1-C6Alkoxy of C5-C12Aryl or heteroaryl of (A), preferably C1～C5The alkyl group, alkoxy group, phenyl group, naphthyl group, pyridyl group, pyrrolyl group of (a), more preferably methyl group, isopropyl group, phenyl group, naphthyl group, pyridyl group, the number of substituents may be 1, 2, 3, 4, 5, 6, or 6 or more.
In a preferred embodiment of the present invention, the molecular weight of the compound is between 400-1200, preferably 450-1100, for film-forming and processing properties.
Further, in the general formula (I) of the present invention, the following compounds of specific structures can be preferably selected: A1-A21, these compounds being representative only.
The pyrene derivative parent structure with the polycyclic conjugated characteristic has high bond energy among atoms and good thermal stability; the solid accumulation among the middle molecules is facilitated, and the service life of the material is prolonged;
as a representative example, the HOMO and LUMO of pyrene derivative compounds were well separated. In addition, the pyrene derived compound structure has small energy difference delta Est value combined with a triplet state and a singlet state, and thermal excitation delayed fluorescence (TADF) is easily realized, and as a representative example, the results of the delta Est of some compounds are as follows:
the invention also provides application of the organic electroluminescent compound in preparing organic electroluminescent devices. The organic electroluminescent device of the present invention is not different from known devices in structure, and generally comprises a first electrode, a second electrode and one or more organic layers interposed between the first electrode and the second electrode, characterized in that the organic layers comprise the above organic electroluminescent compound. As the organic layer between the first electrode and the second electrode, there are usually organic layers such as an electron injection layer, an electron transport layer, a light-emitting layer, a hole transport layer, and a hole injection layer. The compound of the present invention can be used as, but not limited to, a material of a light emitting layer, and as a material of a light emitting layer, the compound of the present invention can be used as a host material of the light emitting layer or a guest material of the light emitting layer.
The invention also provides application of the organic electroluminescent compound in preparing organic electroluminescent devices.
Wherein, the organic electroluminescent compound can be used as, but not limited to, a light emitting layer material.
The present invention also provides an organic electroluminescent device comprising a first electrode, a second electrode and one or more organic layers interposed between the first electrode and the second electrode, the organic layers comprising the above organic electroluminescent compound.
When the compound is used as a light-emitting host, the mechanism of host sensitization object is adopted, the triplet excitons of the host can be rapidly transferred to the light-emitting object through the TADF process, the triplet excitons are more effectively utilized, the problem of serious efficiency roll-off is avoided, the light-emitting efficiency of the organic electroluminescent device is improved, and the compound is suitable for green and red light-emitting devices; when the compound is used as a light-emitting object, the compound can receive the energy transferred by the host, realize the reverse gap crossing from a triplet state to a singlet state, improve the exciton utilization rate and be suitable for a green light device. The HOMO and LUMO energy levels of the compound are adjusted through specific substituent modification, all the groups of a parent structure are effectively connected, the band gap of the material is adjusted, the technical problem of low-efficiency roll-off of a green device under low doping concentration when the compound is used as a host material is solved, the service life is long, and the compound is more suitable for material options of the green 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.
In particular, the compound in the general formula (I) can be used as a light-emitting layer material in an organic electroluminescent device without limitation.
Specific methods for producing the above-described novel compounds of the present invention will be described in detail below by way of examples of synthesis, but the production method of the present invention is not limited to these examples of synthesis, and those skilled in the art can make modifications, equivalents, improvements, etc. without departing from the principles of the present invention and extend the methods to the scope of the claims of the present invention.
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. Various chemicals used in examples such as petroleum ether, ethyl acetate, N-hexane, toluene, tetrahydrofuran, methylene chloride, carbon tetrachloride, acetone, 1, 2-bis (bromomethyl) benzene, CuI, phthaloyl chloride, phenylhydrazine hydrochloride, trifluoroacetic acid, acetic acid, trans-diaminocyclohexane, iodobenzene, cesium carbonate, potassium phosphate, ethylenediamine, benzophenone, cyclopentanone, 9-fluorenone, sodium tert-butoxide, methanesulfonic acid, 1-bromo-2-methylnaphthalene, o-dibromobenzene, butyllithium, dibromoethane, o-dibromobenzene, benzoyl peroxide, 1- (2-bromophenyl) -2-methylnaphthalene, N-bromosuccinimide, methoxymethyltrimethylphosphonium chloride, tris (dibenzylideneacetone) dipalladium, tetrakis (triphenylphosphine) palladium, 1, 3-bis (diphenylphosphinopropane nickel chloride, potassium chloride, Basic chemical raw materials such as carbazole, 3, 6-dimethylcarbazole, 3- (2-naphthyl) -6-phenylcarbazole, N-phenylcarbazole-3-boric acid, 9- (2-naphthyl) carbazole-3-boric acid and the like can be purchased in domestic chemical product markets.
Analytical testing of intermediates and compounds in the present invention use AB SCIEX mass spectrometer (4000QTRAP) and brueck nuclear magnetic resonance spectrometer (400M).
Synthesis examples:
synthesis example 1 Synthesis of Compound A1
Pyrene was selected as a starting material, and 20.2g of pyrene (0.1mol) was dissolved in a mixed solution of 400mL of CH2Cl2, 400mL of CH3CN and 1000mL of water, and 175g (0.8mol) of sodium periodate and 2.5g (12mmol) of RuCl3 were added to the mixed solution. The mixture was kept at 30-40 ℃ and heated for 12h overnight. After the reaction, 3.5L of water was added to the mixture and stirred vigorously. The aqueous phase was then extracted 5 times with 2L of CH2Cl 2. The organic phases were combined, washed with brine and dried. The organic phase was concentrated to give 4.4g of intermediate M1 as a dark yellow solid in 17% yield. Adding an intermediate M1(0.1mol,1eq.) and 200ml of toluene into a 1L three-necked bottle under the protection of nitrogen, starting stirring, adding ethylenediamine (5eq), heating to reflux, reacting for 4h, adding MnO2 into the reaction solution, continuing heating, refluxing for 2h, filtering the reaction solution, washing the filtrate with water, separating an organic phase, drying, concentrating, recrystallizing with ethanol to obtain an intermediate M2(4.8g, 92.3%)
Under the protection of nitrogen, 100ml of acetic acid is added into a 250ml reaction bottle, the intermediate 2(0.05mol, 1eq) is added, stirring is started, bromine (1.1eq) is added dropwise, stirring is carried out, and reaction is carried out for 3 hours. Pouring the reaction solution into water, filtering, and washing the filtrate with water and ethanol. Recrystallization from toluene gave intermediate M3(4.2g, 87.5%).
Under the protection of nitrogen, 3, 6-diphenylcarbazole (0.05mol, 1.0eq), intermediate 3(1.05eq), sodium tert-butoxide (1.5eq) and 500mL of toluene are added into a 1L three-necked bottle, Pd2(dba)3 (0.5% eq) is added, 10% tri-tert-butylphosphine (1% eq) is injected into the bottle by a syringe, stirring is started, the bottle is heated to 100 ℃, the reaction is carried out overnight, the temperature is reduced to about 50 ℃, 2L of toluene is added for dilution, 3000mL of toluene is added for washing, liquid separation is carried out, an organic phase is dried, a flash column (the amount of silica gel is used), the washing liquid is black, concentration is carried out, and yellow solid powder 14.2g is obtained by filtration, and the yield is 61%.
Nuclear magnetic spectroscopic data for compound a 1:
1H NMR(400MHz,Chloroform)9.27(s,5H),9.04(d,J＝7.3Hz,10H),8.25(s,5H),8.01(d,J＝20.0Hz,7H),7.87(s,2H),7.85–7.48(m,24H),7.41(s,3H),7.41(s,8H),7.41(s,9H).
synthesis example 2 Synthesis of Compound A2
Pyrene was selected as a starting material, and 20.2g of pyrene (0.1mol) was dissolved in a mixed solution of 400mL of CH2Cl2, 400mL of CH3CN and 1000mL of water, and 175g (0.8mol) of sodium periodate and 2.5g (12mmol) of RuCl3 were added to the mixed solution. The mixture was kept at 30-40 ℃ and heated for 12h overnight. After the reaction, 3.5L of water was added to the mixture and stirred vigorously. The aqueous phase was then extracted 5 times with 2L of CH2Cl 2. The organic phases were combined, washed with brine and dried. The organic phase was concentrated to give 4.4g of intermediate M1 as a dark yellow solid in 17% yield.
Adding the intermediate 1(0.1mol,1eq.) and 200ml of toluene into a 1L three-necked bottle under the protection of nitrogen, starting stirring, adding ethylenediamine (5 eq.), heating to reflux, reacting for 4h, adding MnO2 into the reaction solution, continuing heating, refluxing for 2h, filtering the reaction solution, washing the filtrate with water, separating an organic phase, drying, concentrating, recrystallizing with ethanol to obtain an intermediate M2(4.8g, 92.3%)
Under the protection of nitrogen, 100ml of acetic acid is added into a 250ml reaction bottle, the intermediate 2(0.05mol, 1eq) is added, stirring is started, bromine (2.2eq) is added dropwise, stirring is carried out, and reaction is carried out for 3 hours. Pouring the reaction solution into water, filtering, and washing the filtrate with water and ethanol. Recrystallization from toluene gave intermediate M3B (4.2g, 87.5%).
100ml of toluene was added to a 250ml reaction flask under nitrogen protection in an ice bath, intermediate M3B (0.05mol, 1eq) was added, stirring was started, isopropyl magnesium bromide (1.1eq) was added dropwise, and the mixture was stirred and reacted for 3 hours. The reaction solution was poured into water, extracted with ethyl acetate, and the organic phase was concentrated. Recrystallization from toluene gave intermediate M3B (16.2g, 87.5%).
Under the protection of nitrogen, 3, 6-diphenyl-9- (4-boraphenyl) carbazole (0.05mol, 1.0eq), intermediate M3B (1.05eq), sodium carbonate (1.5eq), 500mL of toluene, 200mL of ethanol and 200mL of water are added into a 1L three-necked bottle, Pd2(PPh3)4 (0.5% eq) is added, stirring is started, the temperature is increased to 100 ℃, the reaction is carried out overnight, the temperature is reduced to about 50 ℃, water is added for washing, liquid separation is carried out, an organic phase is dried, a flash column (the amount of silica gel is used), an eluent is black, and the yellow solid powder 15.6g is obtained by concentration and filtration, and the yield is 65%.
Nuclear magnetic spectroscopic data for compound a 2:
1H NMR(400MHz,Chloroform)9.10(s,5H),8.98(d,J＝7.9Hz,10H),8.08(s,5H),7.91(d,J＝4.0Hz,10H),7.89–7.46(m,32H),7.41(s,8H),7.41(s,3H),7.41(s,8H),2.87(s,1H),1.26(s,15H).
synthesis example 3 Synthesis of Compound A3
The compound A3 was synthesized in the same manner as in the previous step except that the intermediate M3B was replaced with M3, and 3, 6-diphenyl-9- (4-boranophenyl) carbazole was replaced with an equivalent amount of 3, 6-diphenyl-9- (3-boranophenyl) carbazole, and after the reaction was completed, 17.1g of a yellow solid was isolated with a yield of 72.3%.
1H NMR(400MHz,Chloroform)8.96(d,J＝12.1Hz,3H),8.81(s,2H),8.39(s,2H),8.21(s,1H),8.04(s,1H),7.99(s,2H),7.91(d,J＝8.5Hz,5H),7.94–7.31(m,12H),7.41(s,2H),7.41(s,1H).
Synthesis example 4 Synthesis of Compound A4
The synthesis procedure was identical to compound a3, except that intermediate M3 was replaced with M3B and 12.7g of a yellow solid was isolated in 58.3% yield after the reaction was complete.
1H NMR(400MHz,Chloroform)8.98(d,J＝12.7Hz,18H),8.81(s,10H),8.50(s,10H),8.39(s,10H),8.21(s,5H),7.89(d,J＝2.9Hz,2H),7.87(s,9H),7.77–7.31(m,76H),7.41(s,10H),7.41(s,6H).
Synthesis example 5 Synthesis of Compound A5
The compound A3 was used in the synthesis step, except that 3, 6-diphenyl-9- (4-boranophenyl) carbazole was replaced with an equivalent amount of 3, 6-diphenyl-9- (2, 6-dimethyl-4-boranophenyl) carbazole, and after the reaction was completed, 11.9g of a yellow solid was isolated with a yield of 60.5%.1H NMR(400MHz,Chloroform)9.09(s,4H),8.98(d,J＝7.2Hz,8H),8.09–7.96(m,10H),7.85(d,J＝20.0Hz,6H),7.78–7.47(m,19H),7.41(s,7H),7.41(s,2H),7.41(s,7H),2.50(s,12H) Synthesis example 6 Synthesis of Compound A6
The synthesis procedure was identical to that of compound A1, except that 3, 6-diphenyl-9- (4-boranophenyl) carbazole was replaced with an equivalent amount of 9, 9-dimethylacridine, and 9.6g of a yellow solid was isolated after the reaction was completed, with a yield of 46.7%.
1H NMR(400MHz,Chloroform)9.00(d,J＝5.4Hz,4H),8.70(s,2H),8.04(s,1H),7.99(s,2H),7.28–7.15(m,6H),6.94(s,2H),1.69(s,6H).
Synthesis example 7 Synthesis of Compound A7
The compound A1 is used in the synthesis step, and the difference is that 3, 6-diphenyl-9- (4-boranophenyl) carbazole is replaced by phenoxazine with equivalent weight, and after the reaction is finished, yellow solid 9.9g is obtained by separation, and the yield is 65.6%.
1H NMR(400MHz,Chloroform)9.03(d,J＝5.4Hz,16H),8.93(s,8H),8.04(s,4H),7.99(s,8H),7.08(d,J＝52.0Hz,18H),6.98(s,7H),6.93(s,8H).
Synthesis example 8 Synthesis of Compound A8
And mixing the intermediate M3B with equivalent CuCN, putting the mixture into DMF, heating to 120 ℃, reacting overnight, washing with water after the reaction is finished, extracting with ethyl acetate, and concentrating to obtain an intermediate M4B.
The compound A2 was synthesized by a procedure different from that of the intermediate M4 was replaced with M4B, 3, 6-diphenyl-9- (4-boranophenyl) carbazole was replaced with an equivalent amount of 3, 5-dicarbazolyl phenylboronic acid, and after the reaction was completed, 11.5g of a yellow solid was isolated with a yield of 74.3%.
1H NMR (400MHz, Chloroform) 9.01-8.89 (m,4H),8.66(s,1H),8.55(s,1H),8.18(d, J ═ 8.0Hz,2H),7.52(s,1H),7.40(s,1H),7.16(dd, J ═ 22.0,14.0Hz,4H)
The synthesis step is identical to the compound A1, except that 3, 6-diphenylcarbazole is replaced by equivalent diphenyldiamine, and after the reaction is finished, yellow solid 16.4g is obtained by separation, and the yield is 82.4%.
1H NMR(400MHz,Chloroform)9.00(d,J＝9.2Hz,4H),8.50(s,2H),8.08(d,J＝8.4Hz,1H),8.01(d,J＝10.0Hz,3H),7.75(s,4H),7.52(d,J＝24.0Hz,9H),7.45(d,J＝4.8Hz,1H),7.39(d,J＝16.0Hz,8H).
Synthesis example 10 Synthesis of Compound A10
The compound A3 was used in the synthesis procedure, except that 3, 6-diphenyl-9- (4-boranophenyl) carbazole was replaced with an equivalent amount of 3, 6-bis (2-naphthyl) -9- (3-boranophenyl) carbazole, and after the reaction was completed, 13.0g of a yellow solid was isolated with a yield of 75.4%.
1H NMR(400MHz,Chloroform)8.85(d,J＝12.0Hz,4H),8.62(s,2H),8.50(s,2H),8.21(s,1H),8.12–7.89(m,9H),8.12–7.42(m,22H),7.48(d,J＝12.0Hz,2H),7.45(t,J＝24.0Hz,3H),7.36(d,J＝2.8Hz,1H).
Synthesis example 11 Synthesis of Compound A11
The compound A3 was used in the synthesis step, except that 3, 6-diphenyl-9- (4-boranophenyl) carbazole was replaced with an equivalent amount of 3, 6-diisopropyl-9- (2, 6-dimethyl-4-boranophenyl) carbazole, and after the reaction was completed, 14.3g of a yellow solid was isolated with a yield of 67.9%.
1H NMR(400MHz,Chloroform)9.00(dd,J＝13.2,4.4Hz,14H),8.19(s,2H),8.04(s,2H),7.99(s,4H),7.82(s,4H),7.52(s,2H),7.40(s,3H),7.29(s,1H),7.15(s,2H),2.87(s,3H),2.50(s,12H),1.20(s,24H).
Synthesis example 12 Synthesis of Compound A12
The compound A2 was synthesized in the same manner except that isopropyl magnesium bromide was replaced with an equivalent amount of phenylmagnesium bromide, 3, 6-diphenyl-9- (4-boranophenyl) carbazole was replaced with an equivalent amount of 1, 8-dimethyl-9- (4-boranophenyl) carbazole, and after the reaction was completed, 13.5g of a yellow solid was isolated with a yield of 72.8%.
1H NMR(400MHz,Chloroform)9.01(d,J＝16.0Hz,18H),8.92(s,6H),8.45(s,3H),8.09(s,3H),7.91(d,J＝4.0Hz,12H),7.75(s,7H),7.49(s,5H),7.41(s,4H),7.14(s,2H),7.01(d,J＝16.0Hz,7H),6.92(s,2H),2.50(s,18H).
Synthesis example 13 Synthesis of Compound A13
The synthesis step is identical to the compound A8, except that 3, 5-dicarbazolylphenylboronic acid is replaced by 3, 6-biphenylyl-9- (3-bromophenyl) carbazole in an equivalent amount, and after the reaction is finished, 15.4g of yellow solid is obtained by separation, and the yield is 76.1%.
1H NMR(400MHz,Chloroform)8.85(d,J＝12.0Hz,2H),8.47(d,J＝8.0Hz,2H),8.21(s,6H),7.89(s,1H),7.75(dd,J＝12.0,8.0Hz,4H),7.60(d,J＝4.0Hz,1H),7.56–7.44(m,4H),7.41(s,7H),7.30(s,1H),7.25(s,4H).
Synthesis example 14 Synthesis of Compound A14
The synthesis procedure was identical to compound a3, except that 3, 6-diphenyl-9- (4-boranophenyl) carbazole was replaced with an equivalent amount of 3, 5-dibenzothiophenylboronic acid, and after the reaction was complete, 10.6g of a yellow solid was isolated in a yield of 69.8%.
1H NMR(400MHz,Chloroform)8.86(s,2H),8.80(d,J＝13.3Hz,4H),8.04(s,1H),7.99(s,2H),7.25–7.05(m,12H),6.95(d,J＝16.0Hz,7H).
Synthesis example 15 Synthesis of Compound A15
The synthesis step was carried out using compound A4, except that 3, 6-diphenyl-9- (3-boranophenyl) carbazole was replaced with an equivalent amount of 3, 6-bis (2-naphthylbiphenyl) -9- (3-boranophenyl) carbazole, and after the reaction, 10.4g of a yellow solid was isolated with a yield of 67.8%.1H NMR(400MHz,Chloroform)8.54(d,J＝16.4Hz,2H),8.31(d,J＝12Hz,1H),8.20(s,1H),8.08(d,J＝12.0Hz,2H),7.93(d,J＝12.0Hz,2H),7.73(s,3H),7.71(s,6H),7.68–7.53(m,4H),7.45(t,J＝12.0Hz,2H),7.25(s,3H),7.18(s,1H),7.02(s,1H).
Synthesis example 16 Synthesis of Compound A16
The compound A3 was used in the synthesis step, except that 3, 6-diphenyl-9- (3-boranophenyl) carbazole was replaced with an equivalent amount of 2- (2-triphenylene) -9- (4-boranophenyl) carbazole, and after the reaction was completed, 11.4g of a yellow solid was isolated with a yield of 68.4%.
1H NMR(400MHz,Chloroform)9.60(s,8H),8.84(d,J＝10.4Hz,3H),8.53(d,J＝1.0Hz,1H),8.43(s,1H),8.39–8.28(m,2H),8.13(t,J＝12.0Hz,1H),8.04(s,8H),8.01(d,J＝10.0Hz,2H),8.25–7.80(m,6H),7.70(s,1H),7.64(s,1H),7.47(d,J＝10.0Hz,2H),7.20(d,J＝4.0Hz,1H),7.13(d,J＝10.0Hz,1H).
Synthesis example 17 Synthesis of Compound A17
The compound A3 was used in the synthesis step, except that 3, 6-diphenyl-9- (3-boranophenyl) carbazole was replaced with an equivalent amount of 5-phenyl-7- (4-boranophenyl) indolocarbazole, and after the reaction was completed, 9.6g of a yellow solid was isolated with a yield of 12.5%.
1H NMR(400MHz,Chloroform)9.06(dd,J＝10.0,8.0Hz,2H),8.55(d,7H),8.19(s,3H),8.04(s,3H),7.99(s,7H),7.92(d,J＝4.0Hz,1H),7.60(d,J＝16.0Hz,1H),7.51(d,J＝8.0Hz,1H),7.40(s,3H),7.16(dd,J＝16.0,8.0Hz,1H).
Synthesis example 18 Synthesis of Compound A18
The synthesis process of the compound A8 was the same as that of the compound A8, except that 3, 5-dicarbazolylphenylboronic acid was replaced by an equivalent amount of 3- (9, 9-dimethylfluorene) -9- (4-boranophenyl) carbazole, and after the reaction was completed, 10.4g of a yellow solid was isolated with a yield of 57.5%.
1H NMR(400MHz,Chloroform)9.94(s,1H),9.00(s,3H),8.99–8.88(m,3H),8.55(s,1H),8.09(s,1H),8.01–7.85(m,5H),7.69(d,J＝12.0Hz,2H),7.51(d,J＝8.0Hz,2H),7.42(d,J＝8.4Hz,8H),7.34(s,1H),7.24(s,1H),7.13(d,J＝10.0Hz,4H),1.69(s,12H).
Synthesis example 19 Synthesis of Compound A19
The synthesis step is identical to the compound A1, except that 3, 6-diphenylcarbazole is replaced by equivalent 3, 6-dicyclohexylcarbazole, and after the reaction is finished, yellow solid 13.9g is obtained by separation, and the yield is 64.2%.
1H NMR(400MHz,Chloroform)9.22(s,2H),9.03(d,J＝5.4Hz,4H),8.96(s,1H),8.19(s,1H),8.08(d,J＝8.5Hz,4H),8.01(d,J＝10.0Hz,4H),7.52(s,1H),7.38(d,J＝12.1Hz,2H),7.15(s,1H),2.61(s,4H),2.03(s,4H),1.60(s,6H),1.51(s,6H),1.12(s,6H).
Synthesis example 20 Synthesis of Compound A20
The compound A3 was used in the synthesis step, except that 3, 6-diphenyl-9- (3-boranophenyl) carbazole was replaced with an equivalent amount of 3- (2-spirofluorenyl) -9- (4-boranophenyl) carbazole, and after the reaction was completed, 15.8g of a yellow solid was isolated with a yield of 69.5%.
1H NMR(400MHz,Chloroform)9.04(s,1H),8.81(d,J＝10.9Hz,2H),8.55(s,1H),8.39(s,1H),8.13–7.97(m,3H),7.98(d,J＝14.0,4H),7.82–7.32(m,4H),7.34(s,5H),7.34(s,2H),7.24(d,J＝4.0Hz,2H),7.13(d,J＝10.0Hz,2H).
Synthesis example 21 Synthesis of Compound A21
The compound A3 was used in the synthesis step, except that 3, 6-diphenyl-9- (3-boranophenyl) carbazole was replaced with an equivalent amount of 11, 11-dimethyl-5-fluorenocarbazole, and after the reaction was completed, 12.5g of a yellow solid was isolated with a yield of 65.3%.
1H NMR(400MHz,Chloroform)9.09–8.96(m,6H),8.55(s,1H),8.38(s,1H),8.24(s,2H),8.04(s,1H),7.99(s,2H),7.91(d,J＝8.0Hz,4H),7.51(dd,J＝12.4,8.0Hz,4H),7.30(d,J＝12.0Hz,3H),7.20(t,J＝6.4Hz,3H),7.13(d,J＝10.0Hz,2H),1.69(s,6H).
Analytical test data for specific preferred synthetic structural compounds disclosed in the examples of the present invention are listed in table 1 below:
TABLE 1
| Sample (I) | Molecular formula | Molecular weight | Elemental analysis |
| A1 | C44H25N5 | 623.2 | C,84.33；H,4.00；N,11.15 |
| A2 | C53H35N5 | 741.5 | C,85.69；H,4.34；N,9.35 |
| A3 | C50H29N5 | 699.4 | C,85.99；H,4.04；N,10.00 |
| A4 | C50H28BrN5 | 777.2 | C,77.12；H,3.46；N,8.67 |
| A5 | C52H33N5 | 727.1 | C,85.75；H,4.46；N,9.38 |
| A6 | C35H23N5 | 513.0 | C,81.78；H,4.36；N,13.45 |
| A7 | C32H17N5O | 487.4 | C,78.38；H,3.26；N,14.45； |
| A8 | C51H27N7 | 737.3 | C,83.00；H,3.54；N,13.21 |
| A9 | C44H27N5 | 625.3 | C,84.38；H,4.24；N,11.14 |
| A10 | C58H33N5 | 799.6 | C,87.00；H,4.04；N,8.38 |
| A11 | C46H37N5 | 659.0 | C,83.45；H,5.28；N,10.45 |
| A12 | C46H29N5 | 651.4 | C,84.56；H,4.72；N,10.69 |
| A13 | C63H36N6 | 876.0 | C,86.12；H,4.05；N,9.42 |
| A14 | C50H28N6S2 | 776.8 | C,77.23；H,3.45；N,10.69； |
| A15 | C70H40BrN5 | 1029.5 | C,81.55；H,3.91；Br,7.75； |
| A16 | C56H31N5 | 773.2 | C,86.94；H,4.02；N,9.01 |
| A17 | C50H28N6 | 712.5 | C,84.47；H,3.57；N,11.62 |
| A18 | C54H32N6 | 764.7 | C,84.93；H,4.13；N,10.64 |
| A19 | C44H37N5 | 635.0 | C,83.08；H,5.54；N,11.31 |
| A20 | C63H35N5 | 861.9 | C,87.90；H,4.21；N,8.03 |
| A21 | C47H29N5 | 663.4 | C,85.46；H,4.27；N,10.38 |
Device embodiment:
the typical structure of the OLED organic electroluminescent device prepared in the device example is:
substrate/anode/Hole Injection Layer (HIL)/Hole Transport Layer (HTL)/organic light Emitting Layer (EL)/Electron Transport Layer (ETL)/Electron Injection Layer (EIL)/cathode
The "/" mentioned above indicates that different functional layers are stacked in order.
The inventive compounds of this patent can be used in, but are not limited to, host materials for light emitting layers and guest materials for light emitting layers.
Device example 1-1 (comparative).
The structure of the organic electroluminescent device in the embodiment of the device is as follows:
ITO/2-TNATA(30nm)/NPB(20nm)/EML(20nm)/Bphen(50nm)/LiF(1nm)/Al。
the material of the luminescent layer uses green phosphorescent guest material Ir (ppy)3The main CBP is matched. The molecular structure of each functional layer material is as follows:
the preparation process of the organic electroluminescent device in the embodiment is as follows:
ultrasonically cleaning a glass substrate coated with an ITO transparent conductive film on the surface in a cleaning solution, ultrasonically treating the glass substrate in deionized water, and performing ultrasonic treatment in ethanol: ultrasonically removing oil in an acetone mixed solution, baking in a clean environment until water is completely removed, etching and performing ozone treatment by using an ultraviolet lamp, and bombarding the surface by using low-energy cation beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, performing vacuum evaporation on the anode layer film to form 2-TNATA, adjusting the evaporation rate to be 0.1nm/s, and forming a hole injection layer with the thickness of 30 nm; evaporating a compound NPB on the hole injection layer in vacuum to form a hole transport layer with the thickness of 20nm, wherein the evaporation rate is 0.1 nm/s; the method comprises the following steps of performing vacuum evaporation on an EML (Electron absorption layer) on a hole transport layer to serve as a light emitting layer of a device, wherein the EML comprises a host material and an object material, adjusting the evaporation rate of the host material CBP to be 0.1nm/s by using a multi-source co-evaporation method, setting the evaporation rate of the object material Ir (ppy)3 according to a doping proportion, and setting the total evaporation film thickness to be 20 nm;
taking Bphen as an electron transport layer material of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 50 nm;
LiF with the thickness of 1nm 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 cathode of the device.
Device examples 1-2. Compounds of the invention as light emitting host materials
An organic electroluminescent device was produced in the same manner as in example 1, except that CBP was replaced with compound a 1.
Device examples 1-3. Compounds of the invention as light emitting host materials
An organic electroluminescent device was produced in the same manner as in example 1, except that CBP was replaced with compound a 2.
Device examples 1-4. Compounds of the invention as light emitting host materials
An organic electroluminescent device was produced in the same manner as in example 1, except that CBP was replaced with compound a 5.
Device examples 1-5 Compounds of the invention as light emitting host materials
An organic electroluminescent device was produced in the same manner as in example 1, except that CBP was replaced with compound a 6.
Device examples 1-6 Compounds of the invention as light emitting host materials
An organic electroluminescent device was produced in the same manner as in example 1, except that CBP was replaced with compound a 11.
Device examples 1-7 Compounds of the invention as light emitting host materials
An organic electroluminescent device was produced in the same manner as in example 1, except that CBP was replaced with compound a 13.
Device examples 1-8 Compounds of the invention as light emitting host materials
An organic electroluminescent device was produced in the same manner as in example 1, except that CBP was replaced with compound a 15.
The device performance detection data of the specific preferred structural compound disclosed in the embodiment of the invention applied to the organic electroluminescent device are detailed in the following table 2:
TABLE 2
In device examples 1-2 to 1-8 and device example 1-1 (comparative example), under the condition that other materials in the organic electroluminescent device structure are the same, the series of compounds of the invention replace CBP in comparative device example 1 to be used as a phosphorescent main body material of a light-emitting layer, the working voltage of the device is obviously reduced from 4.9, the current efficiency is obviously improved from 28cd/A, the photoelectric performance of the material structure of the invention has a very obvious improvement effect compared with the comparative example in the device with the same structure, and meanwhile, the service life of the device is greatly prolonged. The series of compounds of the invention have the property of thermal excitation delayed fluorescence, and the compounds are used as the luminescent host material with long range
Energy transfer is transmitted to the object to emit light, compared with the traditional host through short-distance Dexter energy transfer, exciton transfer is more effective, materials of the series are better matched with each other, the object doping concentration of the device is reduced, high light emitting efficiency is achieved, and cost is reduced.
Device example 2-1 (comparative).
The structure of the organic electroluminescent device in the embodiment of the device is as follows:
ITO/2-TNATA(30nm)/NPB(20nm)/EML(20nm)/Bphen(50nm)/LiF(1nm)/Al。
the material of the luminescent layer is used as a green fluorescent guest or host, and is matched with host H1 or guest D1.
The preparation process of the organic electroluminescent device in the embodiment is as follows:
ultrasonically cleaning a glass substrate coated with an ITO transparent conductive film on the surface in a cleaning solution, ultrasonically treating the glass substrate in deionized water, and performing ultrasonic treatment in ethanol: ultrasonically removing oil in an acetone mixed solution, baking in a clean environment until water is completely removed, etching and performing ozone treatment by using an ultraviolet lamp, and bombarding the surface by using low-energy cation beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, performing vacuum evaporation on the anode layer film to form 2-TNATA, adjusting the evaporation rate to be 0.1nm/s, and forming a hole injection layer with the thickness of 30 nm; evaporating a compound NPB on the hole injection layer in vacuum to form a hole transport layer with the thickness of 20nm, wherein the evaporation rate is 0.1 nm/s; EML is evaporated on the hole transport layer in vacuum and used as a light emitting layer of a device, the EML comprises a host material and an object material, the evaporation rate of the host material H1 is adjusted to be 0.1nm/s by using a multi-source co-evaporation method, the evaporation rate of the object material D1 is set according to the doping proportion of 5%, and the total thickness of the evaporation film is 20 nm;
taking Bphen as an electron transport layer material of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 50 nm;
LiF with the thickness of 1nm 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 cathode of the device.
Device examples 2-2. Compounds of the invention as light emitting guest materials
An organic electroluminescent device was produced in the same manner as in example 1, except that D1 was replaced with compound a 1.
Device examples 2-3. Compounds of the invention as light emitting guest materials
An organic electroluminescent device was produced in the same manner as in example 1, except that D1 was replaced with compound a 6.
Device examples 2-4. Compounds of the invention as light emitting guest materials
An organic electroluminescent device was produced in the same manner as in example 1, except that D1 was replaced with compound a 7.
Device examples 2-5 Compounds of the invention as light emitting guest materials
An organic electroluminescent device was produced in the same manner as in example 1, except that D1 was replaced with compound a 9.
Device examples 2-6 Compounds of the invention as light emitting guest materials
An organic electroluminescent device was produced in the same manner as in example 1, except that D1 was replaced with compound a 14.
Device examples 2-7 Compounds of the invention as light emitting host materials
An organic electroluminescent device was produced in the same manner as in example 1, except that H1 was replaced with compound a 4.
Device examples 2-8 Compounds of the invention as light emitting host materials
An organic electroluminescent device was produced in the same manner as in example 1, except that H1 was replaced with compound a 10.
Device examples 2-9 Compounds of the invention as light emitting host materials
An organic electroluminescent device was produced in the same manner as in example 1, except that H1 was replaced with compound a 12.
The device performance detection data of the specific preferred structural compound disclosed in the embodiment of the invention applied to the organic electroluminescent device are detailed in the following table 3:
TABLE 3
The series of compounds have thermal excitation delay fluorescence properties, are matched with a fluorescent host or an object, can easily realize reverse gap crossing due to small energy difference between a triplet state and a singlet state, enable a triplet state energy level to be transferred to the singlet state, further emit light, and realize energy utilization of the triplet state and the singlet state.
The preferred embodiments of the present invention have been described in detail, however, the present invention is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solution of the present invention within the technical idea of the present invention, and these simple modifications are within the protective scope of the present invention.
It should be noted that the various technical features described in the above embodiments can be combined in any suitable manner without contradiction, and the invention is not described in any way for the possible combinations in order to avoid unnecessary repetition.
In addition, any combination of the various embodiments of the present invention is also possible, and the same should be considered as the disclosure of the present invention as long as it does not depart from the spirit of the present invention.
Claims (14)
1. A compound, the structure of which is represented by the following general formula (I),
wherein:
indicates the site of attachment,
l is selected from the group consisting of a bond, C6-C12Arylene of, C3-C12The heteroarylene group of (a);
R1selected from hydrogen, substituted or unsubstituted C1～C12Alkyl, halogen, cyano, nitro, hydroxy, C6～C30Substituted or unsubstituted aromatic hydrocarbon group of (A), C3～C30Substituted or unsubstituted heteroaryl of (a);
R3、R4、R5、R6independently selected from hydrogen, substituted or unsubstituted C1～C12Alkyl, halogen, cyano, nitro, hydroxy, silyl, C6～C30Substituted or unsubstituted aromatic hydrocarbon group of (A), C10～C30Substituted or unsubstituted heteroaryl of (a); r7、R8Independent of each otherIs selected from hydrogen, substituted or unsubstituted C1～C12Alkyl, cyclopentyl, cyclohexyl, halogen, cyano, nitro, hydroxy, silyl, C6～C30Substituted or unsubstituted aromatic hydrocarbon group of (A), C10～C30Substituted or unsubstituted heteroaryl of (a);
x is C (R)b)2、NRcO, S; n is equal to 0, 1;
m, r, p, q, s and t are independently 0,1 or 2; when R is 2, two R3The same or different; when m is 2, two R4The same or different; when p is 2, two R5The same or different; when q is 2, two R6The same or different; when s is 2, two R7The same or different; when t is 2, two R8The same or different, and the like,
Ra、Rband RcIndependently selected from hydrogen, C1-C5Alkylene, halogen, cyano, nitro, hydroxy of (a); two RbThe same or different, or a combination thereof,
when the defined group is a substituted group, the substituent on the substituted group is selected from halogen, nitro, cyano, C1-C6Alkyl of (C)1-C6Alkoxy group of (C)5-C12An aryl or heteroaryl group.
2. The compound of claim 1, wherein the substituents on the pyrene structure attached to Ar are axisymmetric.
3. A compound according to claim 1, said R7With R in symmetrical position8Are the same substituents.
4. The compound according to claim 1, selected from one of the following compounds:
5. a compound, the structure of which is represented by the following general formula (I),
wherein:
indicates the site of attachment,
l is a substituted phenylene group;
R1selected from hydrogen, substituted or unsubstituted C1～C12Alkyl, halogen, cyano, nitro, hydroxy, silyl, C6～C30Substituted or unsubstituted aromatic hydrocarbon group of (A), C3～C30Substituted or unsubstituted heteroaryl of (a);
R3、R4、R5、R6、R7、R8independently selected from hydrogen, substituted or unsubstituted C1～C12Alkyl, halogen, cyano, nitro, hydroxy, silyl, C6～C30Substituted or unsubstituted aromatic hydrocarbon group of (A), C10～C30Substituted or unsubstituted heteroaryl of (a);
x is C (R)b)2、NRcO, S; n is equal to 0, 1;
m, r, p, q, s and t are independently 0,1 or 2; when R is 2, two R3The same or different; when m is 2, two R4The same or different; when p is 2, two R5The same or different; when q is 2, two R6The same or different; when s is 2, two R7The same or different; when t is 2, two R8The same or different, and the like,
Ra、Rband RcIndependently selected from hydrogen, C1-C5Alkylene, halogen, cyano, nitro, hydroxy of (a); two RbThe same or different, or a combination thereof,
when a defined group is a substituted group, the substituent is on the substituted groupThe substituent is selected from halogen, nitro, cyano, C1-C6Alkyl of (C)1-C6Alkoxy group of (C)5-C12An aryl or heteroaryl group.
6. The compound of claim 5, wherein the substituents on the pyrene structure attached to Ar are axisymmetric.
7. A compound according to claim 5, said R7With R in symmetrical position8Are the same substituents.
8. The compound of any one of claims 1-3, 5-7, said aromatic hydrocarbon groups independently being selected from phenyl, phenyl substituted with furyl, thienyl, pyrrolyl and/or pyridyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof, fluoranthryl, triphenylene, pyrenyl, perylenyl,
at least one of a phenyl group and a tetracenyl group.
9. The compound of any one of claims 1-3, 5-7, the heteroaryl group being at least one selected from furanyl, phenylfuranyl, thienyl, phenylthienyl, pyrrolyl, phenylpyrrolyl, pyridyl, phenylpyridyl, pyrazinyl, fluorenyl, indenofluorenyl, quinoline, triazinyl, benzofuranyl, benzothienyl, benzotriazine, benzopyrazine, isobenzofuranyl, indolyl, benzoquinoline, dibenzofuranyl, dibenzothienyl, dibenzopyrrolyl, carbazolyl and derivatives thereof, phenyl-substituted diazoles, phenanthrolinyl, phenanthrolinothiazolyl, and benzodioxolyl.
10. The compound according to claim 5, selected from one of the following compounds:
11. a compound selected from one of the following compounds:
12. an organic electroluminescent device comprising a first electrode, a second electrode and one or more organic layers interposed between the first and second electrodes, characterized in that the organic layers comprise a compound according to any one of claims 1 to 11.
13. An organic electroluminescent device according to claim 12, the organic layer comprising a light-emitting layer comprising a compound according to any one of claims 1 to 10.
14. The organic electroluminescent device according to claim 12 or 13, which is a green or red light emitting device.
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| CN110129038A (en) * | 2019-06-10 | 2019-08-16 | 武汉华星光电半导体显示技术有限公司 | Peony thermal activation delayed fluorescence material and its production method, electroluminescent device |
| CN113429399B (en) * | 2021-07-10 | 2024-03-26 | 浙江华显光电科技有限公司 | Pyrene derivative, light-emitting device material and light-emitting device |
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