CN111662238A - Heat activated fluorescent material with electron acceptor fragment composed of carbon-hydrogen atoms and application thereof - Google Patents
Heat activated fluorescent material with electron acceptor fragment composed of carbon-hydrogen atoms and application thereof Download PDFInfo
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Abstract
The invention relates to a compound shown in formula (I), which has the following structural formula:
wherein X is selected from an oxygen atom, a sulfur atom or a phenylimino group. The above compound has the heat-activated fluorescence property, the electron acceptor fragment in the compound only consists of hydrocarbon atoms, and the compound can be used for preparing the compound with low voltage drive and higher external quantumAn efficient organic electroluminescent device.
Description
Technical Field
The invention relates to the field of fluorescent materials, in particular to a thermal activation fluorescent material with an electron acceptor segment composed of carbon and hydrogen atoms and application thereof.
Background
The organic electroluminescent device is a current type semiconductor luminescent device based on organic materials, the basic structure of which belongs to a sandwich structure, the classical structure is that a layer of organic luminescent material is made on ITO glass to be used as a luminescent active layer, and a layer of metal electrode is added above the luminescent layer. Through further optimization, the device efficiency is improved, and an electron transport layer and a hole transport layer can be increased. When an external voltage is applied to the device, holes and electrons generated by the anode and the cathode are compounded into excitons in the luminescent material, the energy of the excitons is transferred to luminescent molecules, so that the electrons in the luminescent molecules are excited to an excited state, and photons are emitted outwards through a fluorescence or phosphorescence process. The LED display panel has the characteristics of all solid state, self luminescence, wide viewing angle, high response speed, low driving voltage, low energy consumption and the like, and has great application prospect in the fields of panel display and solid light sources.
The light-emitting layer is generally composed of a host material and a dopant dye, and the ratio of singlet excitons to triplet excitons formed by recombination in the light-emitting layer is 1:3, the traditional fluorescent device can only utilize singlet excitons to emit light, and the maximum internal quantum efficiency is about 25 percent. And the phosphorescence material can obtain nearly 100% internal quantum efficiency due to the introduction of Ir and Pt atoms. However, the heavy metals in phosphorescent materials are costly and non-renewable, which limits their practical application to some extent. In recent years, a thermally activated delayed-mechanism fluorescent material is widely used as a light emitting dye of an OLED device, which can simultaneously use singlet excitons having a generation probability of 25% and triplet excitons having a generation probability of 75% to obtain high light emitting efficiency.
At present, most of electron acceptor fragments in the thermal activation delayed mechanism fluorescent material contain heteroatoms except carbon and hydrogen atoms, and the bond dissociation energy of the acceptor fragments is generally smaller. When the thermal activation delayed fluorescent material designed by adopting the electron acceptor segments is prepared into an organic electroluminescent device, the stability of the device is not high, and the service life of the device is reduced.
Disclosure of Invention
In order to solve the above technical problems, the present invention provides a thermally activated fluorescent material with an electron acceptor fragment composed of carbon hydrogen atoms and applications thereof, and the present invention provides a compound with thermally activated fluorescent properties, wherein the electron acceptor fragment in the compound is an aromatic group composed of only carbon hydrogen atoms; the compound of the present invention can be used for preparing an organic electroluminescent device having low voltage driving and higher external quantum efficiency.
The first object of the present invention is to provide a compound represented by the formula (I) having the following structural formula:
wherein X is selected from an oxygen atom, a sulfur atom or a phenylimino group. Preferably, X is an oxygen atom.
In the compound of formula (I), the electron acceptor fragment is
The group is of a pure hydrocarbon structure, only contains two atoms of carbon atoms and hydrogen atoms, does not contain other heteroatoms, is favorable for obtaining higher bond dissociation energy, is favorable for improving the stability of a device, and prolongs the service life of the device.
In the compound shown in the formula (I), the electron donating group is
X is selected from oxygen atom, sulfur atom or phenylimino, the electron donating group at least contains an electron-rich aromatic group containing nitrogen atom, and the nitrogen atom is directly connected with the electron acceptor segment. When X is selected from oxygen atom, sulfur atom or phenylimino group, the electron-donating group is phenoxazin-10-yl, phenothiazin-10-yl or 5-phenyl-5, 10 dihydrophenazine in sequence, and preferably phenoxazin-10-yl.
When X is a phenylimino group, the structural formula of the compound represented by the formula (I) is as follows:
further, the preparation method of the compound shown in the formula (I) comprises the following steps:
(S1) reacting the compound shown in the formula (3) with iodine bromide (IBr) in an organic solvent at 20-30 ℃, and obtaining the compound shown in the formula (4) after the reaction is completed;
(S2) reacting the compound represented by the formula (4) with the compound represented by the formula (2) in an organic solvent in the presence of a base and a palladium salt catalyst at 95 to 105 ℃ (preferably 100 ℃) to obtain the compound represented by the formula (1); the reaction route is as follows:
wherein X is selected from an oxygen atom, a sulfur atom or a phenylimino group.
Further, in the step (S1), the molar ratio of the compound represented by formula (3) to iodine bromide is 1:1 to 1: 1.5. Preferably, the molar ratio of the compound represented by formula (3) to iodine bromide is 1: 1.1.
Further, in the step (S2), the molar ratio of the compound represented by formula (4) to the compound represented by formula (2) is 1:1 to 1: 2. Preferably, the molar ratio of the compound represented by formula (4) to the compound represented by formula (2) is 1: 1.2.
Further, in the step (S2), a ligand selected from tri-tert-butylphosphine (P (t-Bu) is used in the reaction process3) And triphenylphosphine.
Further, in step (S2), the base is selected from potassium carbonate, sodium carbonate, cesium carbonate and the like, and cesium carbonate is preferable from the viewpoint of good yield, and the molar ratio of the base to the compound represented by formula (4) is not particularly limited, and 2:1 is preferable from the viewpoint of good yield.
Further, in the step (S2), the palladium salt catalyst is selected from palladium acetate, palladium chloride, palladium trifluoroacetate, palladium nitrate, and the like. The catalyst is not particularly limited as long as it is a catalytic amount that can function as a catalyst. From the viewpoint of good yield, the molar ratio of the palladium catalyst to the compound represented by the formula (4) is preferably 1:30 to 10.
Further, in the steps (S1) and (S2), the organic solvent is selected from toluene, tetrahydrofuran, 1, 4-dioxane, dimethyl sulfoxide, dimethylformamide, etc., preferably toluene.
Further, the step (S1) may further include a step of purifying the compound represented by formula (1), and if necessary, the compound may be purified by recrystallization, column chromatography, sublimation, or the like.
The above preparation method can obtain the target product in good yield.
The second purpose of the invention is to disclose the application of the compound shown in the formula (I) in preparing the heat-activated delayed fluorescent material.
The third purpose of the invention is to disclose the application of the compound shown in the formula (I) in preparing an organic electroluminescent device.
It is a fourth object of the present invention to provide an organic electroluminescent device comprising a light-emitting layer comprising a dopant dye comprising a compound represented by formula (I):
wherein X is selected from an oxygen atom, a sulfur atom or a phenylimino group.
Further, the light-emitting layer further includes a host material selected from 1, 3-bis (9-hydro-carbazol-9-yl) -benzene (mCP), bis [2- ((oxo) diphenylphosphino) phenyl ] ether, and the like.
Further, the mass ratio of the host material to the doping dye is 1: 0.04-1: 0.2.
Further, the organic electroluminescent device comprises a substrate, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer and a cathode layer which are sequentially arranged.
Furthermore, the thickness of the hole transport layer is 30-45nm, the thickness of the electron blocking layer is 5-10nm, the thickness of the light emitting layer is 15-25nm, the thickness of the electron transport layer is 40-55nm, and the thickness of the cathode layer is 100 nm.
By the scheme, the invention at least has the following advantages:
the invention provides a compound shown in formula (I), wherein an electron acceptor fragment of the compound is only composed of carbon atoms and hydrogen atoms, other hetero atoms are not contained in the electron acceptor fragment, and the compound shown in formula (I) has a thermal activation delayed fluorescence characteristic and can be used for preparing materials of organic electroluminescent devices, particularly used as a fluorescence dopant.
The organic electroluminescent device adopting the compound shown in the formula (I) as the dopant has the characteristics of lower driving voltage, higher external quantum efficiency and the like.
The foregoing description is only an overview of the technical solutions of the present invention, and in order to make the technical solutions of the present invention more clearly understood and to implement them in accordance with the contents of the description, the following description is made with reference to the preferred embodiments of the present invention and the accompanying detailed drawings.
Drawings
FIG. 1 is a schematic sectional view of an organic electroluminescent device produced in example 2 of the present invention;
FIG. 2 shows the luminance and current density test results of an organic electroluminescent device prepared in example 2 of the present invention;
FIG. 3 is a graph of the electroluminescence intensity versus wavelength of an organic electroluminescent device prepared in example 2 of the present invention;
fig. 4 shows the results of testing the power efficiency and external quantum efficiency of the organic electroluminescent device prepared in example 2 of the present invention.
Description of reference numerals:
1-a glass substrate; 2-a hole transport layer; 3-an electron blocking layer; 4-a light-emitting layer; 5-an electron transport layer; 6-cathode layer.
Detailed Description
The following examples are given to further illustrate the embodiments of the present invention. The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
Example 1: preparation of 10- (acenaphtho [3,2,1,8-fghij ] picene-7-yl) -10-hydroxyphenoxazine
Wherein X is an oxygen atom.
A compound represented by the formula (3) (2mmol, 0.7g) and ultra-dry methylene chloride (30.0mL), CH of IBr2Cl2The solution (4ml, 1.0M) was mixed well and the resulting mixture was stirred at room temperature for 4h, quenched with sodium hydrogen sulfate and extracted with dichloromethane and water. The organic phase was then washed with anhydrous Na2SO4Drying, and removing the residual solvent in the organic phase under reduced pressure to obtain a solid, namely the compound shown in the formula (4).
The solid obtained under reduced pressure (0.25g) was added to toluene, followed by the addition of phenoxazine (1.1mmol,0.2g), Pd (OAc)2(30mg)，P(t-Bu)3(1mL)，Cs2CO3(960mg) was heated to 100 ℃ and stirred under nitrogen for 10 hours. After cooling to room temperature, it was then purified by column chromatography on silica gel to give 138mg of an orange-yellow product in 26% yield. The structure of the product is characterized, and the result is as follows:
1H NMR(400MHz,CDCl3)8.81-8.73(m,2H),8.66(dt,J＝11.5,5.5Hz,1H),8.59(dd,J＝7.9,1.2Hz,1H),8.49-8.41(m,2H),8.33(s,1H),8.23(d,J＝8.9Hz,1H),8.02(d,J＝8.8Hz,1H),7.87-7.73(m,4H),6.86-6.76(m,2H),6.68(tt,J＝6.3,3.2Hz,2H),6.54-6.41(m,2H),6.03-5.93(m,2H).MS(EI)m/z:[M]+calced for C40H21NO 531.16,found530.92.
10- (acenaphtho [3,2,1,8-fghij ] picene-7-yl) -10-phenothiazine and 10- (acenaphtho [3,2,1,8-fghij ] picene-7-yl) -10 phenyl-5, 10-dihydrophenazine were prepared, respectively, according to the above-described methods. Except that the phenoxazine in the above step was replaced with an equimolar amount of phenothiazin-10-yl or 5-phenyl-5, 10 dihydrophenazine. The results of structural characterization of the product are as follows:
10- (acenaphtho [3,2,1,8-fghij ] picene-7-yl) -10-hydrophenothiazine:
1H NMR(400MHz,CDCl3)8.97-8.86(m,2H),8.75(d,J＝8.5Hz,1H),8.65(d,J＝8.3Hz,1H),8.52-7.44(m,2H),8.31-8.21(d,J＝8.1Hz,2H),8.04(t,J＝7.5Hz,2H),7.82-7.74(d,J＝7.8Hz,3H)7.52-6.41(d,J＝7.2Hz,6H),7.04-6.92(m,2H).MS(EI)m/z:[M]+calced for C40H21NS 547.24,found 547.15.
10- (acenaphtho [3,2,1,8-fghij ] picene-7-yl) -10 phenyl-5, 10-dihydrophenazine:
1H NMR(400MHz,CDCl3)8.90-8.82(m,2H),8.67(t,J＝8.1Hz,4H),8.49(s,1H),7.92-7.80(m,6H),7.16-7.08(m,9H),6.83-6.74(d,J＝7.1Hz,4H).MS(EI)m/z:[M]+calcedfor C46H26N2606.21,found 606.57.
example 2:
the organic electroluminescent device was fabricated and performance evaluated using 10- (acenaphtho [3,2,1,8-fghij ] picene-7-yl) -10-hydrophenazine prepared in example 1 as a fluorescent dopant dye. The organic electroluminescent device is composed of a glass substrate 1, a hole transport layer 2, an electron blocking layer 3, a light emitting layer 4, an electron transport layer 5, and a cathode layer 6 (fig. 1) which are sequentially arranged.
The method comprises the steps of adopting a 15 omega Indium Tin Oxide (ITO) transparent electrode glass substrate, washing the ITO substrate with isopropanol, water and acetone before an organic light-emitting device is manufactured by vacuum evaporation, then drying the ITO substrate in a blast drying oven at 100 ℃, and then performing surface treatment by adopting an ultraviolet ozone cleaning machine. Finally, the glass substrate 1 was placed in a vacuum evaporation apparatus and evaporation of each layer was carried out by vacuum evaporation to produce a light-emitting area of 10mm as shown in FIG. 1 in a cross-sectional view2The organic electroluminescent device has the following specific manufacturing process:
on the glass substrate 1, a hole transport layer 2, an electron blocking layer 3, a light emitting layer 4, an electron transport layer 5, and a cathode layer 6 are sequentially vapor-deposited. 4,4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline ] (TAPC) with a vapor-deposited film thickness of 35nm was used as the hole transport layer 2, 4' -tris (carbazol-9-yl) triphenylamine (TCTA) with a vapor-deposited film thickness of 10nm was used as the electron blocking layer 3, 1, 3-bis (9 hydro-carbazol-9-yl) -benzene (mCP) with a vapor-deposited film thickness of 20nm in a ratio of 9:1 (mass%) and 10- (acenaphtho [3,2,1,8-fghij ] picene-7-yl) -10-hydrophenazine synthesized in example 1 of the present invention was used as the light emitting layer 4, and 3,3' - [5' - [3- (3-pyridyl) phenyl ] [1,1':3', 1' -terphenyl ] -3 with a vapor-deposited film thickness of 45nm was used as the light emitting layer 4, 3' -diyl ] bipyridine (TmPyPb) as the electron transport layer 5. Wherein each organic material is formed into a film by means of resistance heating. The materials of each layer are evaporated at a rate of 0.1-0.2 nm/s. Finally, lithium fluoride and aluminum were deposited in film thicknesses of 1nm and 100nm, respectively, as the cathode layer 6. Each film thickness was measured by a stylus type film thickness measuring instrument (DEKTAK).
The prepared organic electroluminescent device was subjected to direct current application, evaluated for light emission performance using a Spectrascan PR655 luminance meter, and measured for current-voltage characteristics using a computer-controlled Keithley 2400 digital source meter. As the light emission characteristics, the starting voltage and the maximum luminance (cd/m) were measured under the condition that the voltage varied with the applied DC voltage2) CIE color coordinate values, external quantum efficiency (EQE,%) and power efficiency (PE, lm/W). As shown in FIGS. 2 to 4, the measured values of the devices fabricated above were 3.1eV, 15650cd/m2(0.38,0.57), 20% and 68.1 lm/W.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, it should be noted that, for those skilled in the art, many modifications and variations can be made without departing from the technical principle of the present invention, and these modifications and variations should also be regarded as the protection scope of the present invention.
Claims (10)
1. A compound of formula (I) having the formula:
wherein X is selected from an oxygen atom, a sulfur atom or a phenylimino group.
2. The compound according to claim 1, characterized in that its preparation process comprises the following steps:
(S1) reacting the compound shown in the formula (3) with iodine bromide in an organic solvent at 20-30 ℃, and obtaining the compound shown in the formula (4) after the reaction is completed;
(S2) reacting the compound shown in the formula (4) with the compound shown in the formula (2) in an organic solvent at 95-105 ℃ in the presence of alkali and a palladium salt catalyst to obtain the compound shown in the formula (1); the reaction route is as follows:
wherein X is selected from an oxygen atom, a sulfur atom or a phenylimino group.
3. The compound according to claim 2, wherein in step (S1), the molar ratio of the compound represented by formula (3) to iodine bromide is 1:1 to 1: 1.5.
4. The compound according to claim 2, wherein in step (S2), the molar ratio of the compound represented by formula (4) to the compound represented by formula (2) is 1:1 to 1: 2.
5. The compound of claim 2, wherein in step (S2), a ligand selected from tri-tert-butylphosphine or triphenylphosphine is further used in the reaction.
6. Use of a compound of formula (I) according to claim 1 for the preparation of a thermally activated delayed fluorescence material.
7. Use of a compound of formula (I) according to claim 1 for the preparation of an organic electroluminescent device.
8. An organic electroluminescent device comprising a light-emitting layer, wherein the light-emitting layer comprises a doped dye, and wherein the doped dye comprises a compound represented by formula (I):
wherein X is selected from an oxygen atom, a sulfur atom or a phenylimino group.
9. The organic electroluminescent device according to claim 8, wherein the light-emitting layer further comprises a host material selected from 1, 3-bis (9-hydro-carbazol-9-yl) -benzene or bis [2- ((oxo) diphenylphosphino) phenyl ] ether.
10. The use according to claim 8 or 9, wherein the mass ratio of the host material to the doping dye is 1: 0.04-1: 0.2.
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| CN109776535A (en) * | 2017-11-15 | 2019-05-21 | 苏州大学 | Orange light-red light material, preparation method with planar structure and its application in organic electroluminescence device |
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| GUOPIN XU ET AL.,: "Chemistry on the rim of buckybowls: derivatization of 1,2,5,6-tetrabromocorannulene", 《TETRAHEDRON LETTERS》 * |
| KENSUKE OTA ET AL.,: "meso‑β Dibenzo[a,g]corannulene-Fused Porphyrins", 《ORGANIC LETTERS》 * |
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