CN109535131B - Compound taking cyanopyridine as receptor and application thereof - Google Patents
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Abstract
The invention discloses a compound taking cyanopyridine as a receptor and application thereof, belonging to the technical field of organic electroluminescent materials. The general structural formula of the compound is shown as the following formula (I-1), (I-2) or (I-3): wherein D is1、D2Same or different, D1、D2Each independently is an acceptor group; a. the1、A2Identical or different, A1、A2Each independently an electron donating group. The compound provided by the invention can be used as a doping material and/or a main material of an OLED (organic light emitting diode) to realize high brightness, low voltage, high efficiency and long service life of an organic electroluminescent device; the material prepared from the compounds has higher thermal stability, can obviously improve the luminous stability of the light-emitting device, and is widely applied to OLED light-emitting devices and display devices.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to a compound taking cyanopyridine as a receptor and application thereof.
Background
The luminous mechanism of an Organic Light Emitting Diode (OLED) display lighting element, which is a self-luminous electronic element, is a novel photoelectric information technology for directly converting electric energy into Light energy by means of an Organic semiconductor functional material under the action of a direct current electric field. The light emission color can be red, green, blue, yellow alone or combined white. The biggest characteristics of the OLED light-emitting display technology are ultrathin, high response speed, ultralight weight, surface light-emitting and flexible display, can be used for manufacturing monochromatic or panchromatic displays, can be used as a novel light source technology, and can also be used for manufacturing lighting products or a novel backlight source technology for manufacturing liquid crystal displays.
Organic electroluminescent elements (organic EL elements) can be classified into two types, i.e., fluorescent type and phosphorescent type, according to the principle of light emission. When a voltage is applied to the organic EL element, holes from the anode and electrons from the cathode are injected, and they are recombined in the light-emitting layer to form excitons. According to the electron spin statistic method, singlet excitons and triplet excitons are generated in a ratio of 25% to 75%. The fluorescent type uses singlet excitons to emit light, and thus its internal quantum efficiency can only reach 25%. The phosphorescent material is composed of heavy metal elements, and can utilize singlet state energy and triplet state energy simultaneously through interstitial penetration, and the internal quantum efficiency can reach 100%. A Thermally Active Delayed Fluorescence (TADF) material is a third generation organic light emitting material developed after organic fluorescent materials and organic phosphorescent materials. The material generally has smaller singlet-triplet energy level difference (delta Est), triplet excitons can be converted into singlet excitons through reverse gap crossing to emit light, the singlet excitons and the triplet excitons formed under electric excitation can be fully utilized, the internal quantum efficiency of the device can reach 100%, and meanwhile, the material has controllable structure, stable property, low price, no need of precious metal and wide application prospect in the field of OLEDs. The research results in recent years show that: the TADF material can be used not only as a luminescent material (dopant) in a luminescent layer, but also as a host material in the luminescent layer to sensitize the dopant, which is helpful for improving the efficiency of conventional devices, improving the color purity of the devices, and increasing the service life of the devices, and is an organic electroluminescent functional material with a wide application prospect.
An organic electroluminescent device is required to have improved luminous efficiency, reduced driving voltage, improved durability, and the like. Wherein, it is a major subject in the industry to improve the efficiency and the device lifetime. In order to prepare a high-performance OLED light-emitting device, a high-performance OLED functional material needs to be selected and used, and for OLED functional materials with different functions, the basic requirements needed to be met are as follows:
1. the material has good thermal stability, namely, the material can not be decomposed in the long-time evaporation process, and meanwhile, the material is required to have good process reproducibility;
2. the OLED light-emitting device manufactured by matching with the OLED functional material has good performance, namely, better efficiency, longer service life and lower voltage are required. This requires materials with the appropriate highest molecular occupied orbital (HOMO), lowest molecular unoccupied orbital (LUMO), and appropriate triplet energies.
3. As the TADF material, firstly, the material has small singlet state and triplet state energy difference delta Est (generally < 0.1eV), and in addition, the TADF material has proper phosphorescence lifetime.
4. In the face of increasingly urgent market demands, the cost of the material is an important index for judging whether the industrialization can be realized, so that the synthesis route is simple, and the low cost of the raw material plays an important role in rapidly introducing the OLED terminal material into the market.
In recent years, although the development of OLED functional materials has made some breakthrough, as lighting or display applications, there is a need to develop and innovate materials with better performance, especially organic functional materials with longer lifetime and higher efficiency that can be applied to host materials of phosphorescent OLED systems and TADF systems.
Disclosure of Invention
The invention aims to provide a compound taking cyanopyridine as an acceptor, which is applied to an organic electroluminescent device as a luminescent layer material and can obviously improve the device performance of the organic electroluminescent device.
The invention provides a compound taking cyanopyridine as a receptor, which has a structural general formula shown as the following formula (I-1), (I-2) or (I-3):
wherein D is1、D2Being an acceptor group, D1、D2Are respectively and independently selected from cyanopyridine groups shown in formula (II),
A1、A2is an electron-donating group, A1、A2Each independently selected from substituted or unsubstituted carbazolyl, substituted or unsubstituted dicarbazolyl, formula (III), formula (IV), formula (V), formula (VI), formula (VII), or formula (VIII) 21:
when A is1、A2When the substituents are respectively and independently selected from substituted carbazolyl or substituted dicarbazolyl, the substituents are alkyl, phenyl and biphenyl of C1-C6, which are substituted at the N position;
in the formula (III), L represents a hydrogen atom or a phenylene group; ar (Ar)1、Ar2Each independently selected from any one of substituted or unsubstituted aryl or condensed ring aryl of C6-C30, substituted or unsubstituted condensed heterocyclic group of C6-C30, five-membered heterocyclic ring, six-membered heterocyclic ring or substituted heterocyclic ring, and substituted or unsubstituted amino;
in the formula (IV), R1、R2Are respectively and independently selected from hydrogen atoms, alkyl of C1-C6, alkoxy of C1-C6, cyano, trifluoromethyl and fluoro;
R3、R4each independently selected from hydrogen atom, substituted or unsubstituted aryl or condensed ring aryl of C6-C30, substituted or unsubstituted condensed heterocyclic group of C6-C30, five-membered, six-membered heterocyclic ring or substituted heterocyclic ring, and substituted or unsubstituted amino;
in the formula (V), X is oxygen atom, sulfur atom, C-m1m2、Si-m1m2Or N-m3；
Wherein: m is1、m2Are respectively and independently selected from hydrogen atoms, alkyl groups of C1-C6, phenyl or biphenyl;
m3is any one of hydrogen atom, substituted or unsubstituted aryl or condensed ring aryl of C6-C30, substituted or unsubstituted condensed heterocyclic group of C6-C30, five-membered heterocyclic ring, six-membered heterocyclic ring or substituted heterocyclic ring, and substituted or unsubstituted amino;
in the formulae (VI) and (VII), Y is a carbon atom or a silicon atom.
Preferably, in formula (III), Ar is1、Ar2Each independently selected from phenyl, biphenyl, naphthyl, amino, carbazolyl, furanyl, dibenzofuranyl, thienyl, dibenzothienyl, fluorenyl, 9-dimethylfluorenyl, dibenzopyridyl, dibenzooxazinyl, or pheno oxazinyl;
when Ar is1、Ar2When substituted, the substituent is one of methyl, isopropyl, tert-butyl, methoxy, phenyl, cyano, biphenyl, naphthyl, amino, carbazolyl, furyl, dibenzofuryl, thienyl, dibenzothienyl, fluorenyl, dibenzopyridyl, dibenzooxazinyl, or pheno oxazinyl.
More preferably, the group represented by formula (III) is selected from one of the following structural formulae:
preferably, R1、R2Each independently selected from hydrogen atom, methyl, ethyl, propyl, tert-butyl, methoxy, ethoxy, cyano, trifluoromethyl or fluoro;
R3、R4each independently selected from any one of a hydrogen atom, a phenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a dianilino group, a trianilino group, a dibenzopyridyl group, a dibenzooxazinyl group, a fluorenyl group and a 9, 9-dimethylfluorenyl group.
More preferably, the group represented by formula (IV) is selected from one of the following structural formulae:
preferably, in the formula (V), m1、m2Each independently selected from any one of a hydrogen atom, a methyl group, an ethyl group, a propyl group, a tert-butyl group, a phenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzopyridinyl group, a dibenzooxazinyl group, a carbazolyl group, an N-phenylcarbazolyl group, a triphenylamine group, a fluorenyl group and a 9, 9-dimethylfluorenyl group;
m3selected from phenyl, amino, biphenyl,Naphthyl, carbazolyl, furyl, thienyl, fluorenyl, dibenzofuryl, dibenzothienyl, N-phenylcarbazolyl, triphenylamine, 9-dimethylfluorenyl, dibenzopyridyl, phena oxazinyl, dibenzofuran-4-yl- (9, 9-dimethyl-9H-fluoren-2-yl) -amine, 3, 9-diphenyl-9H-carbazolyl, 3-dibenzofuran-4-yl-9-phenyl-9H-carbazolyl, 3- (9, 9-dimethyl-9H-fluoren-1-yl) -9-phenyl-9H-carbazolyl, 12-dimethyl-12H-10-oxa-indeno [2,1-B]Any one of fluorenyl groups and spirobifluorenyl groups.
More preferably, the formula (V) is selected from one of the following structural formulae:
preferably, the cyanopyridine receptor compound is specifically one of the following compounds:
the second purpose of the invention is to provide the application of the compound taking cyanopyridine as an acceptor in an organic electroluminescent device.
The third object of the present invention is to provide an organic electroluminescent device, which comprises a light-emitting layer, wherein the material of the light-emitting layer comprises any one of the above compounds with cyanopyridine as an acceptor, such as the material which can be used as a phosphorescent host and/or a thermal activity delayed fluorescence light-emitting material of the light-emitting layer.
A fourth object of the present invention is to provide an application of the above organic electroluminescent device in an organic electroluminescent display device.
Compared with the prior art, the compound taking cyanopyridine as the acceptor has a donor-pi-acceptor structure, a small delta Est energy value and a proper HOMO/LUMO value, and can realize high brightness, low voltage, high efficiency and long service life of an organic electroluminescent device. Meanwhile, the material prepared from the compound has higher thermal stability, can remarkably improve the luminous stability of a luminous device, and can be widely applied to OLED luminous devices and display devices as a luminous layer main body material or a thermal activity delay fluorescence luminous material.
Drawings
Fig. 1 is a schematic structural diagram of an organic electroluminescent device provided in an embodiment of the present invention.
Description of reference numerals:
1. the cathode layer comprises a substrate, 2, an anode layer, 3, a hole injection layer, 4, a first hole transport layer, 5, a second hole transport layer, 6, a light emitting layer, 7, a hole blocking layer, 8, an electron transport layer, 9, an electron injection layer, 10 and a cathode layer.
Detailed Description
In order to make the technical solutions of the present invention better understood and implemented by those skilled in the art, the present invention is further described below with reference to the following specific embodiments and the accompanying drawings, but the embodiments are not meant to limit the present invention.
The experimental methods and the detection methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
The compound taking cyanopyridine as an acceptor is formed by bonding two electron-donating groups A on a phenyl group1、A2And two acceptor groups D1、D2。
When donor A is present1And A2Of the receptor D1And D2When all are ortho-positions, the structural general formula is shown as the following formula (I-1):
when donor A is present1And A2Of the receptor D1And D2When the two are meta-position, the structural general formula is shown as the following formula (I-2):
when donor A is present1And A2Of the receptor D1And D2When both are para-positions, the general structural formula is shown as the following formula (I-3):
in the above-mentioned formulae (I-1), (I-2) and (I-3), D1、D2Are respectively and independently selected from cyanopyridine groups shown in formula (II),
A1、A2each independently selected from substituted or unsubstituted carbazolyl, substituted or unsubstituted dicarbazolyl, formula (III), formula (IV), formula (V), formula (VI), formula (VII) or formula (VIII):
when A is1、A2When the substituents are respectively and independently selected from substituted carbazolyl or substituted dicarbazolyl, the substituents are alkyl, phenyl and biphenyl of C1-C6, which are substituted at the N position;
in the formula (III), L represents a hydrogen atom orA phenylene group; ar (Ar)1、Ar2Each independently selected from any one of substituted or unsubstituted aryl or condensed ring aryl of C6-C30, substituted or unsubstituted condensed heterocyclic group of C6-C30, five-membered heterocyclic ring, six-membered heterocyclic ring or substituted heterocyclic ring, and substituted or unsubstituted amino;
in the formula (IV), R1、R2Are respectively and independently selected from hydrogen atoms, alkyl of C1-C6, alkoxy of C1-C6, cyano, trifluoromethyl and fluoro;
R3、R4each independently selected from hydrogen atom, substituted or unsubstituted aryl or condensed ring aryl of C6-C30, substituted or unsubstituted condensed heterocyclic group of C6-C30, five-membered, six-membered heterocyclic ring or substituted heterocyclic ring, and substituted or unsubstituted amino;
in the formula (V), X is oxygen atom, sulfur atom, C-m1m2、Si-m1m2Or N-m3；
Wherein: m is1、m2Are respectively and independently selected from hydrogen atoms, alkyl groups of C1-C6, phenyl or biphenyl;
m3is any one of hydrogen atom, substituted or unsubstituted aryl or condensed ring aryl of C6-C30, substituted or unsubstituted condensed heterocyclic group of C6-C30, five-membered heterocyclic ring, six-membered heterocyclic ring or substituted heterocyclic ring, and substituted or unsubstituted amino;
in the formulae (VI) and (VII), Y is a carbon atom or a silicon atom.
The invention provides an organic small molecular compound, wherein two cyanopyridines of receptor groups are connected with furan, carbazole, thiophene, fluorene, heteroaryl amino, acridine, thiophene oxazine, thia oxazine and other groups through a benzene bridge to form a donor-pi-receptor type compound, and the compound can be used as a doping material or a main body material of an organic electroluminescent diode to realize high brightness, low voltage, high efficiency and long service life of an organic electroluminescent device. The parent body with two cyanopyridines as the core shows stronger electron-withdrawing capability, the electron-donating group is connected on the parent body through a benzene bridge, a bipolar material with a donor-pi-acceptor is constructed, the material has smaller singlet energy and triplet energy difference (delta Est), the reversal from triplet energy to singlet energy can be realized, and the thermal activity delayed fluorescence property (TADF) is realized. The compound provided by the invention has excellent properties when being used as a main material, on one hand, the bipolar characteristic of the compound effectively enriches holes and electrons in a light-emitting layer, increases the recombination zone of excitons, effectively improves the efficiency and the service life of a device, and reduces the attenuation of the efficiency; on the other hand, the TADF material can be used as a main body material with TADF property to effectively sensitize a luminescent material, effectively improve the efficiency and the service life of a device, optimize the spectrum of the TADF material and improve the color purity of the TADF device. As a TADF luminescent material, the invented material can obtain materials with different luminescent colors through the modification of different substituents, and the highest internal quantum efficiency is close to 100 percent.
Next, a specific synthesis method for preparing several intermediates corresponding to the above-mentioned compounds is provided, and the following intermediates 1-1, 1-2, 2-1 and 3-1 are synthesized according to the conventional methods.
(1) Synthesis of intermediate 1
100g of intermediate 1-1, 186g of intermediate 1-2, 203g of potassium carbonate and 23.7g of tetrabutylammonium bromide (TBAB) are added into a 2L three-necked bottle, 800ml of toluene, 200ml of ethanol and 200ml of water are sequentially added, nitrogen is introduced, stirring is carried out for 15min, 2.1g of tetrakis (triphenylphosphine) palladium is added, the mixture is heated to 80 ℃ for reflux reaction for 8h, TLC monitors that the raw materials are completely reacted and then cooled to room temperature, insoluble impurities are removed by filtration, liquid separation is carried out, an organic phase is washed to be neutral by water, anhydrous sodium sulfate is dried, and then silica gel column purification is carried out to obtain 104.5g of intermediate 1, wherein the yield is 89.3%.
(2) Synthesis of intermediate 2
100g of intermediate 2-1, 186g of intermediate 1-2, 203g of potassium carbonate and 23.7g of tetrabutylammonium bromide (TBAB) are added into a 2L three-necked flask, 800ml of toluene, 200ml of ethanol and 200ml of water are sequentially added, nitrogen is introduced, stirring is carried out for 15min, 2.1g of tetrakis (triphenylphosphine) palladium is added, the mixture is heated to 80 ℃ for reflux reaction for 8h, TLC monitors that the raw materials are completely reacted and then cooled to room temperature, insoluble impurities are removed by filtration, liquid separation is carried out, an organic phase is washed to be neutral by water, anhydrous sodium sulfate is dried, and then silica gel column purification is carried out to obtain 107.9g of intermediate 2, wherein the yield is 92.2%.
(3) Synthesis of intermediate 3
100g of intermediate 3-1, 186g of intermediate 1-2, 203g of potassium carbonate and 23.7g of tetrabutylammonium bromide (TBAB) are added into a 2L three-necked bottle, 800ml of toluene, 200ml of ethanol and 200ml of water are sequentially added, nitrogen is introduced, stirring is carried out for 15min, 2.1g of tetrakis (triphenylphosphine) palladium is added, the mixture is heated to 80 ℃ for reflux reaction for 8h, TLC monitors that the raw materials are completely reacted and then cooled to room temperature, insoluble impurities are removed by filtration, liquid separation is carried out, an organic phase is washed to be neutral by water, anhydrous sodium sulfate is dried, and then the mixture is purified by a silica gel column to obtain 101.6g of intermediate 3, wherein the yield is 86.8%.
In the following we specifically exemplify compounds, some of which are cyanopyridines as receptors, and provide methods for the synthesis of these compounds.
Example 1
Adding 23.1g of compound 1-1 and 150ml of DMF into a 250ml three-necked flask, cooling to 0 ℃ in an ice water bath, adding 5.5g of sodium hydride with the mass fraction of 60%, stirring and reacting for 1h at the temperature, adding 20g of intermediate 1, naturally heating to room temperature, continuing to stir and react for 4h, monitoring by TLC, slowly pouring the reaction solution into 3 times of volume of water under the condition of stirring after the raw materials are completely reacted, filtering, washing a filter cake to be neutral by using water, and recrystallizing the obtained crude product by using toluene to obtain 32.1g of compound 1 with the yield of 83.5%.
example 2
example 3
Compound 3 nuclear magnetic spectroscopy data:1H NMR(400MHz,CDCl3)δ9.74(s,2H),9.32(s,2H),8.81(s,2H),7.86(s,1H),7.21(s,1H),7.14(d,J＝7.2,4H),6.96-7.01(m,12H)。
example 4
example 5
example 6
Compound 16 nuclear magnetic spectroscopy data:1H NMR(400MHz,CDCl3)δ9.74(s,2H),9.32(s,2H),8.81(s,2H),8.55(m,4H),8.19(d,J＝7.2,2H),7.94(d,J＝7.2,2H),7.58(d,J＝7.2,2H),7.50(t,J＝7.2,2H),7.35(t,J＝7.2,2H),7.16-7.20(m,4H)。
example 7
Compound 16 was synthesized in a procedure different in that compound 1-1 was replaced with 28.9g of compound 2-1 to give 32.2g of compound 17 in 73.5% yield.
Compound 17 nuclear magnetic spectroscopy data:1H NMR(400MHz,CDCl3)δ9.74(s,2H),9.32(s,2H),8.81(s,2H),7.42(s,2H),7.14-7.19(m,12H),6.95(t,J＝7.2,4H),1.69(s,12H)。
example 8
Compound 16 was synthesized in a procedure different in that compound 1-1 was replaced with 25.3g of compound 3-1 to give 31.8g of compound 18 in 78.6% yield.
Compound 18 nuclear magnetic spectroscopy data:1H NMR(400MHz,CDCl3)δ9.74(s,2H),9.32(s,2H),8.81(s,2H),7.42(s,2H),7.14(d,J＝7.2,4H),6.96-7.01(m,12H)。
example 9
Compound 16 was synthesized in a procedure different in that compound 1-1 was replaced with 45.8g of compound 4-1 to give 40.4g of compound 19 in 68.3% yield.
Compound 19 nuclear magnetic spectroscopy data:1H NMR(400MHz,CDCl3)δ9.74(s,2H),9.32(s,2H),8.81(s,2H),7.90(d,J＝7.2,4H),7.55(d,J＝7.2,4H),7.38-7.42(m,6H),7.28(t,J＝7.2,4H),7.14-7.19(m,12H),6.95(t,J＝7.2,4H)。
example 10
The synthetic procedure was identical to compound 16 except that compound 1-1 was replaced with 35.7g of compound 5-1 to give 34.8g of compound 20 in 69.7% yield;
compound 20 nuclear magnetic spectroscopy data:1H NMR(400MHz,CDCl3)δ9.74(s,2H),9.32(s,2H),8.81(s,2H),7.42(s,2H),7.24(t,J＝7.2,4H),6.95-7.00(m,10H),7.08-7.14(m,12H)。
example 11
Compound 30 nuclear magnetic spectroscopy data:1H NMR(400MHz,CDCl3)δ9.74(s,2H),9.32(s,2H),8.81(s,2H),8.54(m,4H),8.19(d,J＝7.2,2H),7.94(d,J＝7.2,2H),7.50(t,J＝7.2,2H),7.58(d,J＝7.2,2H),7.35(t,J＝7.2,2H),7.16-7.20(m,4H)。
example 12
The synthetic procedure was identical to compound 30 except that compound 1-1 was replaced with 28.9g of compound 2-1 to give 31.9g of compound 31 with a yield of 72.8%;
compound 31 nuclear magnetic spectroscopy data:1H NMR(400MHz,CDCl3)δ9.74(s,2H),9.32(s,2H),8.81(s,2H),7.42(s,2H),7.14-7.19(m,12H),6.95(t,J＝7.2,4H),1.69(s,12H)。
example 13
Compound 30 was used in the synthesis procedure except that compound 1-1 was replaced with 25.3g of compound 3-1 to give 30.9g of compound 32 in 76.2% yield.
Compound 32 nuclear magnetic spectroscopy data:1H NMR(400MHz,CDCl3)δ9.74(s,2H),9.32(s,2H),8.81(s,2H),7.42(s,2H),7.14(d,J＝7.2,4H),6.96-7.01(m,12H)。
example 14
Compound 30 was synthesized in a procedure different from that in which compound 1-1 was replaced with 45.8g of compound 4-1, to give 37.7g of compound 33 in a yield of 63.8%.
Compound 33 nuclear magnetic spectroscopy data:1H NMR(400MHz,CDCl3)δ9.74(s,2H),9.32(s,2H),8.81(s,2H),7.90(d,J＝7.2,4H),7.55(d,J＝7.2,4H),7.38-7.42(t,J＝7.2,6H),7.28(t,J＝7.2,4H),7.14-7.19(m,12H),6.95(t,J＝7.2,4H)。
example 15
Compound 30 was synthesized in a procedure different in that compound 1-1 was replaced with 35.7g of compound 5-1 to give 36.6g of compound 34 in 73.3% yield.
Compound 34 nuclear magnetic spectroscopy data:1H NMR(400MHz,CDCl3)δ9.74(s,2H),9.32(s,2H),8.81(s,2H),7.42(s,2H),7.24(t,J＝7.2,4H),7.08-7.14(m,12H),6.95-7.00(m,10H)。
we performed T separately on some of the compounds and existing materials provided in the above examples of the present invention1Energy levels and HOMO, LUMO energy levels were tested and the results are shown in table 1:
TABLE 1 Compounds T of the invention1Energy level and HOMO, LUMO value
Note: the Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO) are measured by cyclic voltammetry, T1Measured by an F4600 fluorescence spectrum analyzer, the measurement environment was the atmospheric environment.
From table 1, the organic compounds of the present invention have higher triplet energy and more suitable HOMO/LUMO, which are favorable for carrier transport and energy transfer in OLED devices, and can be used as phosphorescent host material, fluorescent host material or TADF host material, and also can be used as TADF light emitting material. The organic electroluminescent device may be, without particular limitation, a phosphorescent device, a fluorescent device or a device containing a Thermally Active Delayed Fluorescence (TADF) material. Therefore, after the compound taking cyanopyridine as the acceptor is applied to the light-emitting layer of the OLED device, the light-emitting efficiency, the service life and other properties of the device can be effectively improved.
In the following, some of the compounds provided by the present invention are used as an example and applied to an organic electroluminescent device as a luminescent layer material (host material and/or doped dye) to verify the excellent effects obtained by the organic electroluminescent device.
The excellent effect of the OLED material applied to the device is detailed through the device performances of device examples 1-9 and comparative examples 1 and 2. The structure manufacturing processes of the device examples 1-9 of the invention are completely the same as those of the comparative examples 1 and 2, the same glass substrate and electrode material are adopted, the film thickness of the electrode material is also kept consistent, and the difference is that the material of the light emitting layer is adjusted as follows.
Device application example
Device example 1
The organic electroluminescent device of the present embodiment has a structure as specifically shown in fig. 1, and includes a substrate 1, an anode layer 2, a hole injection layer 3, a first hole transport layer 4, a second hole transport layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode layer 10, which are sequentially stacked.
Wherein, the anode layer 2 is made of Indium Tin Oxide (ITO) with high common function, the hole injection layer 3 is made of HAT-CN with the thickness of 5 nm; NPB is selected as the material of the first hole transport layer 4, and the thickness is 60 nm; TAPC is selected as a material of the second hole transport layer 5, and the thickness is 15 nm; the light-emitting layer 6 uses the compound 1 as a light-emitting material and DPEPO as a main material, the doping amount ratio is 5 percent, and the thickness is 30 nm; TPBI is selected as the material of the hole blocking layer 7, and the thickness is 10 nm; the material of the electron transport layer 8 is ET-1, and the thickness is 35 nm; liq is selected as the material of the electron injection layer 9, and the thickness is 2 nm; the cathode layer is made of Al and has a thickness of 120 nm.
The structural formula of the basic material used by each functional layer in the device is as follows:
the organic electroluminescent device is prepared by the following specific steps:
1) cleaning an ITO anode on a transparent glass substrate, respectively ultrasonically cleaning the ITO anode for 20 minutes by using deionized water, acetone and ethanol, and then carrying out Plasma treatment for 5 minutes in an oxygen atmosphere;
2) evaporating a hole injection layer material HAT-CN on the ITO anode layer in a vacuum evaporation mode, wherein the thickness of the hole injection layer material HAT-CN is 5nm, and the hole injection layer is used as a hole injection layer;
3) evaporating a hole transport material NPB on the hole injection layer in a vacuum evaporation mode, wherein the thickness of the hole transport material NPB is 60nm, and the hole transport layer is used as a first hole transport layer;
4) evaporating a hole transport material TAPC (titanium polycarbonate) on the first hole transport layer NPB in a vacuum evaporation mode, wherein the thickness of the hole transport material TAPC is 15nm, and the layer serves as a second hole transport layer;
5) co-evaporating a light emitting layer on the second hole transport layer by a vacuum evaporation method, using the compound 1 as a light emitting material (dopant), DPEPO as a host material, and having a doping amount ratio of 5% and a thickness of 30 nm;
6) evaporating a hole blocking material TPBI on the light-emitting layer in a vacuum evaporation mode, wherein the thickness of the hole blocking material TPBI is 10nm, and the layer is used as a hole blocking layer;
7) evaporating an electron transport material ET-1 on the hole blocking layer in a vacuum evaporation mode, wherein the thickness of the electron transport material ET-1 is 35nm, and the electron transport material ET-1 serves as an electron transport layer;
8) evaporating an electron injection material Liq on the electron transport layer in a vacuum evaporation mode, wherein the thickness of the electron injection material Liq is 2nm, and the electron injection layer is used as the electron injection layer;
9) on the electron injection layer, a cathode Al was deposited by vacuum deposition to a thickness of 120nm, and the layer was used as a cathode conductive electrode.
Device example 2
The specific structure was the same as in device example 1 except that compound 2 was used as the dock instead of compound 1.
Device example 3
The specific structure was the same as in device example 1 except that compound 6 was used as the dock instead of compound 1.
Device example 4
The specific structure was the same as in device example 1 except that compound 16 was used as a dopant in place of compound 1.
Device example 5
The specific structure was the same as in device example 1 except that compound 17 was used as a dopant in place of compound 1.
Device example 6
The specific structure was the same as that of device example 1, except that Compound 1 was used as a host material in place of DPEPO, and that dock was Ir (ppy)3And forming the phosphorescent device.
Device example 7
The specific structure was the same as in device example 6, except that Compound 4 was used as a host material in place of Compound 1, and that dock was Ir (ppy)3And forming the phosphorescent device.
Device example 8
The specific structure was the same as in device example 6, except that Compound 16 was used as a host material in place of Compound 1, and that dock was Ir (ppy)3And forming the phosphorescent device.
Device example 9
The specific structure is the same as device example 6, except that dock is compound 32, constituting a Thermally Active Delayed Fluorescence (TADF) device.
Comparative example 1
The specific structure was the same as that of device example 6, except that CBP was used as the host material instead of compound 1.
Comparative example 2
The specific structure was the same as in comparative example 1, except that 4CzIPN was used as the dopant material instead of Ir (ppy)3。
The composition of the devices prepared in inventive device examples 1-9 and comparative examples 1-2 is shown in Table 2:
TABLE 2 comparison table of organic electroluminescent element components of each device example
Connecting the cathode and the anode of each group of organic electroluminescent devices by using a known driving circuit, and testing the voltage-efficiency-current density relation of the OLED devices by adopting a Keithley2400 power supply and a PR670 photometer through a standard method; the service life of the device is tested by a constant current method under the condition that the constant current density is 10mA/cm2The time for the test brightness to decay to 95% of the initial brightness is the device LT95Lifetime, test results are shown in table 3:
table 3 performance results for each group of organic electroluminescent devices
As can be seen from Table 3, the compounds of the present invention are excellent in performance when applied to OLED emitters as host materials and light-emitting materials for light-emitting layers. Compared with the comparative example 1, the luminescent efficiency and the service life of the device example 6, which is the compound 1 used as the phosphorescent main body material, are remarkably improved, the luminescent efficiency is improved by more than 10 percent, and the working life of the device is improved by 1 time; compared with the comparative example 2, the compound 16 of the device example 4 serving as the TADF luminescent material has the advantages that the luminous efficiency is improved by 10%, and the service life of the device is prolonged by 50%. Therefore, the compound provided by the invention is selected as a main material or a luminescent material of the OLED device, and compared with the OLED luminescent device applied by the existing material, the photoelectric properties of the device, such as luminous efficiency, service life, color purity and the like, have good performances, and have great application value and commercial prospect in the application of the OLED device and good industrial prospect.
It will be apparent to those skilled in the art that various changes and modifications may be made in the present invention without departing from the spirit and scope of the invention. Thus, it is intended that such changes and modifications be included within the scope of the appended claims and their equivalents.
Claims (4)
1. A compound taking cyanopyridine as an acceptor is characterized by being one of the following compounds:
2. use of the cyanopyridine-acceptor compound of claim 1 in an organic electroluminescent device.
3. An organic electroluminescent device comprising a light-emitting layer, wherein the material of the light-emitting layer comprises the cyanopyridine-acceptor compound of claim 1.
4. Use of the organic electroluminescent device as claimed in claim 3 in an organic electroluminescent display device.
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