CN112538075B - Fused heterocyclic compound and organic electroluminescent device - Google Patents
Fused heterocyclic compound and organic electroluminescent device Download PDFInfo
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Abstract
The invention discloses a fused heterocyclic compound and an organic electroluminescent device, which have the following structural formula:
wherein, R1-R4 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl with 1-10 carbon atoms, substituted or unsubstituted alkenyl with 2-10 carbon atoms, substituted or unsubstituted alkynyl with 2-10 carbon atoms, substituted or unsubstituted cycloalkyl with 3-10 ring carbon atoms, substituted or unsubstituted aryl with 6-30 ring carbon atoms, or substituted or unsubstituted heteroaryl with 5-30 ring carbon atoms.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a fused heterocyclic compound and an organic electroluminescent device.
Background
Generally, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic substance. The organic electroluminescent device using the organic light emitting phenomenon has wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed characteristics, and is the key point of the current domestic and foreign research.
The research on the improvement of the performance of the organic electroluminescent device includes: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. In order to realize the continuous improvement of the performance of the organic electroluminescent device, not only the innovation of the structure and the manufacturing process of the organic electroluminescent device is required, but also the continuous research and innovation of the organic electro-photoelectric functional material are required, and the organic electroluminescent functional material with higher performance is created.
In terms of the actual needs of the current organic electroluminescent industry, the development of the current organic electroluminescent materials is far from insufficient and far behind the requirements of panel manufacturing enterprises, and the research pace of domestic enterprises is far behind that of American-Japanese-Korean enterprises, so that the research and development of more selectable organic electroluminescent materials are the central focus of the current domestic panel enterprises.
Korean patent No. 10-2009-0054903 discloses an aminoanthracene derivative and an organic electroluminescent device using the same, wherein it is indicated that the substituent must have an amino structure
On the basis, further research is carried out by the inventor.
Disclosure of Invention
The purpose of the invention is as follows: in order to solve the technical problems, the invention provides a fused heterocyclic compound and an organic electroluminescent device.
In order to achieve the purpose of the invention, the technical scheme adopted by the invention is as follows:
a fused heterocyclic compound having the structural formula:
wherein, R1-R4 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl group having 1-10 carbon atoms, substituted or unsubstituted alkenyl group having 2-10 carbon atoms, substituted or unsubstituted alkynyl group having 2-10 carbon atoms, substituted or unsubstituted cycloalkyl group having 3-10 ring-forming carbon atoms, substituted or unsubstituted aryl group having 6-30 ring-forming carbon atoms, or substituted or unsubstituted heteroaryl group having 5-30 ring-forming carbon atoms;
R5-R10 are each independently hydrogen, substituted or unsubstituted aryl with 6-30 ring carbon atoms, or substituted or unsubstituted heteroaryl with 5-30 ring carbon atoms;
R5-R7 are not hydrogen at the same time;
R8-R10 are not hydrogen at the same time;
x is O or S.
Further, R1 to R4 are each independently any one of hydrogen, deuterium, cyano, methyl, ethyl, N-propyl, isopropyl, N-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, pyridyl, pyrimidinyl, triazinyl, anthracenyl, naphthyl, phenanthryl, pyrenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, fluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, and 9,9' -spirobifluorenyl;
the methyl group, ethyl group, N-propyl group, isopropyl group, N-butyl group, isobutyl group, sec-butyl group, tert-butyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, phenyl group, biphenyl group, pyridyl group, pyrimidinyl group, triazinyl group, anthracenyl group, naphthyl group, phenanthryl group, pyrenyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, N-phenylcarbazolyl group, fluorenyl group, 9-dimethylfluorenyl group, 9-diphenylfluorenyl group, 9-methyl-9-phenylfluorenyl group, 9' -spirobifluorenyl group being unsubstituted or a group obtained by substituting at least one hydrogen by deuterium and/or a group obtained by substituting at least one carbon by nitrogen.
Further, R1-R4 are each independently hydrogen, deuterium, cyano, methyl, isopropyl, tert-butyl, phenyl, dibenzofuranyl, dibenzothiophenyl;
said methyl, isopropyl, tert-butyl, phenyl, dibenzofuranyl, dibenzothiophenyl radicals being unsubstituted or being radicals obtained by replacement of at least one hydrogen by deuterium and/or radicals obtained by replacement of at least one carbon by nitrogen.
Further, R5 to R10 are each independently hydrogen, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, triazinyl, anthracenyl, azaanthracenyl, naphthyl, azanaphthyl, phenanthryl, azaphenanthryl, pyrenyl, azapyrenyl;
the phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, triazinyl, anthracyl, azaanthracyl, naphthyl, azanaphthyl, phenanthryl, azaphenanthryl, pyrenyl, azapyrenyl are unsubstituted or are groups wherein at least one hydrogen is substituted by:
phenyl, biphenyl, terphenyl, anthracenyl, naphthyl, phenanthryl, pyrenyl;
the phenyl, biphenyl, terphenyl, anthracenyl, naphthyl, phenanthryl, pyrenyl groups of said substituents being unsubstituted or being groups wherein at least one carbon is substituted by nitrogen and/or wherein at least one hydrogen is substituted by phenyl.
Further, R5-R10 are each independently the following:
further, R5, R7, R8 and R10 are hydrogen, and R6 and R9 are not hydrogen.
Further, the fused heterocyclic compound is any one of the following compounds:
the invention also discloses an organic electroluminescent device which comprises a first electrode, a second electrode and an organic layer formed between the first electrode and the second electrode, wherein the organic layer contains the fused heterocyclic compound.
Further, the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer; at least one of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer contains the above-mentioned fused heterocyclic compound.
Further, the electron transport layer contains the fused heterocyclic compound according to any one of claims 1 to 7.
The room temperature of the invention is 25 +/-5 ℃.
The invention has the beneficial effects that: the organic electroluminescent compound is a strong rigid group, has very good thermal stability and planarity, has very good carrier migration rate, and is a very good material core. The functional group with electron-withdrawing property is added on the main structure, so that the electron transfer property of the material is further improved, and the material can be used as a very organic electroluminescent material. The stability and the service life of the luminescent element prepared by the organic electroluminescent material can be obviously improved.
Drawings
Fig. 1 is a schematic structural diagram of an organic electroluminescent device provided by the present invention;
the reference numbers in the figures represent respectively:
1-anode, 2-hole injection layer, 3-hole transmission layer, 4-electron barrier layer, 5-luminescent layer, 6-hole barrier layer, 7-electron transmission layer, 8-electron injection layer and 9-cathode.
Fig. 2 is a comparison graph of the light emitting life of the organic electroluminescent devices prepared in application example 1 and comparative example 1 of the present invention, and it can be seen from fig. 2 that the light emitting life of the organic electroluminescent device prepared in application example 1 is 134h, and the light emitting life of the organic electroluminescent device prepared in comparative example 1 is 82 h.
Detailed Description
Embodiments of the various aspects are further illustrated and described below. It should be understood that the description herein is not intended to limit the claims to the particular aspects described. On the contrary, it is intended to cover alternatives, modifications, and equivalents as may be included within the spirit and scope of the disclosure as defined by the appended claims.
As used herein, a "Ca to Cb" hydrocarbyl group is defined as a hydrocarbyl group having carbon numbers "a" (inclusive) to "b" (inclusive). As used herein, "a and/or b" means "a" or "b" or "a and b".
As used herein, in "substituted" or "unsubstituted," the term "substituted" means that at least one hydrogen in the group is re-coordinated to deuterium, a hydrocarbyl group, a hydrocarbon derivative group, a halogen group, or a cyano (-CN). The term "unsubstituted" means that at least one hydrogen in the group does not re-coordinate with deuterium, a hydrocarbon group, a hydrocarbon derivative group, a halogen, or a cyano (-CN) group. Examples of the hydrocarbon group or hydrocarbon derivative group may include C1 to C30 alkyl groups, C2 to C30 alkenyl groups, C2 to C30 alkynyl groups, C6 to C30 aryl groups, C5 to C30 heteroaryl groups, C1 to C30 alkylamino groups, C6 to C30 arylamino groups, C6 to C30 heteroarylamino groups, C6 to C30 arylheteroarylamino groups, and the like, but are not limited thereto.
The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
Example 1:
the fused heterocyclic compound 1 is synthesized by the following method:
under the protection of nitrogen, adding compound 1-a (10g, 426.10g/mol, 23.47mmol), compound 1-b (2.1eq, 9.86g, 200.00g/mol, 49.28mmol) and sodium carbonate (4eq, 9.95g, 105.99g/mol, 93.88mmol) into toluene (200ml), ethanol (50ml) and water (50ml), stirring and mixing uniformly, adding tetrakistriphenylphosphine palladium (0.05eq, 1.36g, 1155.58g/mol, 1.17mmol), heating to reflux reaction for 10h, cooling to room temperature, adding water (150ml), stirring to separate out an aqueous phase, extracting the aqueous phase with dichloromethane, combining organic phases, drying the organic phase with anhydrous sodium sulfate, stirring and purifying by silica gel column chromatography to obtain thick heterocyclic compound 1(11.76g, yield 86.9%), ESI-MS (M/z) (M +): theoretical 576.64, found 576.80, elemental analysis result (molecular formula C40H24N 4O): theoretical value C, 83.31; h, 4.20; n, 9.72; o, 2.77; found C, 83.31; h, 4.20; n, 9.72; o, 2.77.
Example 2:
the fused heterocyclic compound 2 is synthesized as follows:
the preparation was substantially the same as in example 1, except that the compound 1-b was replaced with the compound 2-b in 88.2% yield, ESI-MS (M/z) (M +): theoretical 730.81, found 730.74, elemental analysis result (molecular formula C50H30N 6O): theoretical value C, 82.17; h, 4.14; n, 11.50; o, 2.19; found C, 82.17; h, 4.14; n, 11.50; o, 2.19.
Example 3:
the fused heterocyclic compound 5 is synthesized as follows:
s1: under the protection of nitrogen, adding compound 3-a (10g, 473.10g/mol, 21.14mmol), compound 3-b (1.1eq, 4.65g, 200.00g/mol, 23.25mmol) and sodium carbonate (2eq, 4.48g, 105.99g/mol, 42.28mmol) into toluene (200ml), ethanol (50ml) and water (50ml), stirring and mixing uniformly, adding tetrakistriphenylphosphine palladium (0.05eq, 1.22g, 1155.58g/mol, 1.06mmol), heating to reflux reaction for 10h, cooling to room temperature, adding water (150ml), stirring to separate out an aqueous phase, extracting the aqueous phase with dichloromethane, combining organic phases, drying the organic phase with anhydrous sodium sulfate, stirring and purifying by silica gel column chromatography to obtain compound 3-c (9.57g, yield 90.3%), ESI-MS (M/z) (M +): theoretical 501.37, found 502.66, elemental analysis result (molecular formula C30H17BrN 2O): theoretical value C, 71.87; h, 3.42; br, 15.94; n, 5.59; o, 3.19; found C, 71.87; h, 3.42; br, 15.94; n, 5.59; and O, 3.19.
S2: under the protection of nitrogen, adding compound 3-c (9g, 501.37g/mol, 17.95mmol), compound 3-b (1.1eq, 3.95g, 200.00g/mol, 19.75mmol) and sodium carbonate (2eq, 3.81g, 105.99g/mol, 35.9mmol) into toluene (180ml), ethanol (45ml) and water (45ml), stirring and mixing uniformly, adding tetrakistriphenylphosphine palladium (0.05eq, 1.04g, 1155.58g/mol, 0.9mmol), heating to reflux reaction for 10h, cooling to room temperature, adding water (135ml), stirring to separate out an aqueous phase, extracting the aqueous phase with dichloromethane, combining organic phases, drying the organic phase with anhydrous sodium sulfate, stirring and purifying by silica gel column chromatography to obtain thick heterocyclic compound 1(8.76g, yield 84.6%), ESI-MS (M/z) (M +): theoretical 576.64, found 576.82, elemental analysis result (molecular formula C40H24N 4O): theoretical value C, 83.31; h, 4.20; n, 9.72; o, 2.77; found C, 83.31; h, 4.20; n, 9.72; o, 2.77.
Example 4:
the fused heterocyclic compound 18 is synthesized as follows:
the preparation was carried out in substantially the same manner as in example 3 except that the compounds 3-b and 3-d were replaced with the compounds 4-b and 4-d in a yield of 84.5%, ESI-MS (M/z) (M +): theoretical 701.81, found 701.98, elemental analysis result (molecular formula C51H31N 3O): theoretical value C, 87.28; h, 4.45; n, 5.99; o, 2.28; found C, 87.28; h, 4.45; n, 5.99; o, 2.28.
Example 5:
the fused heterocyclic compound 19 is synthesized as follows:
the preparation method was substantially the same as in example 3 except that the compound 3-d was replaced with the compound 5-d in 84.0% yield, ESI-MS (M/z) (M +): theoretical 624.73, found 624.60, elemental analysis (formula C46H28N 2O): theoretical value C, 88.44; h, 4.52; n, 4.48; o, 2.56; found C, 88.44; h, 4.52; n, 4.48; o, 2.56.
Example 6:
the fused heterocyclic compound 23 is synthesized as follows:
the preparation was essentially the same as in example 3, except that compound 3-d was replaced with compound 6-d in 83.3% yield, ESI-MS (M/z) (M +): theoretical 624.73, found 624.81, elemental analysis (formula C46H28N 2O): theoretical value C, 88.44; h, 4.52; n, 4.48; o, 2.56; found C, 88.44; h, 4.52; n, 4.48; o, 2.56.
Example 7:
the fused heterocyclic compound 41 is synthesized as follows:
the preparation was essentially the same as in example 3, except that compound 3-d was replaced with compound 7-d in 80.8% yield, ESI-MS (M/z) (M +): theoretical 700.82, found 700.44, elemental analysis result (molecular formula C52H32N 2O): theoretical value C, 89.12; h, 4.60; n, 4.00; o, 2.28; found C, 89.12; h, 4.60; n, 4.00; o, 2.28.
Example 8:
the fused heterocyclic compound 58 is synthesized as follows:
the preparation was carried out in substantially the same manner as in example 3, except that the compounds 3-b and 3-d were replaced with the compounds 8-b and 8-d in a yield of 81.3%, ESI-MS (M/z) (M +): theoretical 726.82, found 726.83, elemental analysis result (molecular formula C52H30N 4O): theoretical value C, 85.93; h, 4.16; n, 7.71; o, 2.20; found C, 85.93; h, 4.16; n, 7.71; o, 2.20.
Example 9:
the fused heterocyclic compound 64 is synthesized as follows:
the preparation method was substantially the same as in example 3 except that the compounds 3-b, 3-d were replaced with the compounds 9-b, 9-d in a yield of 81.7%, ESI-MS (M/z) (M +): theoretical 725.83, found 725.88, elemental analysis result (molecular formula C53H31N 3O): theoretical value C, 87.70; h, 4.30; n, 5.79; o, 2.20; found C, 87.70; h, 4.30; n, 5.79; o, 2.20.
Example 10:
the fused heterocyclic compound 67 was synthesized as follows:
the preparation was carried out in substantially the same manner as in example 3 except that the compounds 3-b and 3-d were replaced with the compounds 10-b and 10-d in a yield of 78.6%, ESI-MS (M/z) (M +): theoretical 726.82, found 726.40, elemental analysis result (molecular formula C52H30N 4O): theoretical value C, 85.93; h, 4.16; n, 7.71; o, 2.20; found C, 85.93; h, 4.16; n, 7.71; o, 2.20.
Example 11:
the fused heterocyclic compound 81 is synthesized as follows:
the preparation was carried out in substantially the same manner as in example 3 except that the compounds 3-b and 3-d were replaced with the compounds 11-b and 11-d in a yield of 79.6%, ESI-MS (M/z) (M +): theoretical 753.85, found 753.70, elemental analysis result (molecular formula C53H31N 5O): theoretical value C, 84.44; h, 4.14; n, 9.29; o, 2.12; found C, 84.44; h, 4.14; n, 9.29; o, 2.12.
Example 12:
the fused heterocyclic compound 98 is synthesized as follows:
the preparation was carried out in substantially the same manner as in example 3 except that the compounds 3-a, 3-d were replaced with the compounds 12-a, 12-d in a yield of 83.9%, ESI-MS (M/z) (M +): theoretical 564.70, found 564.55, elemental analysis result (molecular formula C40H24N 2S): theoretical value C, 85.08; h, 4.28; n, 4.96; s, 5.68; found C, 85.08; h, 4.28; n, 4.95; and S, 5.68.
Example 13:
the fused heterocyclic compound 104 is synthesized as follows:
the preparation was substantially the same as in example 12, except that the compound 12-d was replaced with the compound 13-d in a yield of 82.7%, ESI-MS (M/z) (M +): theoretical 640.79, found 640.53, elemental analysis result (molecular formula C46H28N 2S): theoretical value C, 86.22; h, 4.40; n, 4.37; s, 5.00; found C, 86.22; h, 4.40; n, 4.37; s, 5.00.
Example 14:
the fused heterocyclic compound 105 is synthesized as follows:
the preparation method was substantially the same as in example 13, except that the compound 13-b was replaced with the compound 14-b, the yield was 82.1%, ESI-MS (M/z) (M +): theoretical 717.88, found 717.93, elemental analysis result (molecular formula C51H31N 3S): theoretical value C, 85.33; h, 4.35; n, 5.85; s, 4.47; found C, 85.32; h, 4.35; n, 5.85; and S, 4.47.
Example 15:
the fused heterocyclic compound 149 is synthesized as follows:
the preparation was carried out in substantially the same manner as in example 13, except that the compounds 13-b and 13-d were replaced with the compounds 15-b and 15-d, and that the yield was 77.9%, ESI-MS (M/z) (M +): theoretical 741.90, found 741.68, elemental analysis result (molecular formula C53H31N 3S): theoretical value C, 85.80; h, 4.21; n, 5.66; s, 4.32; found C, 85.80; h, 4.21; n, 5.66; and S, 4.32.
Example 16:
the fused heterocyclic compound 172 is synthesized as follows:
the preparation was carried out in substantially the same manner as in example 13, except that the compounds 13-a, 13-b and 13-d were replaced with the compounds 16-a, 16-b and 16-d in a yield of 74.3%, ESI-MS (M/z) (M +): theoretical 896.99, found 896.27, elemental analysis result (molecular formula C62H36N6O 2): theoretical value C, 83.02; h, 4.05; n, 9.37; o, 3.57; found C, 83.02; h, 4.05; n, 9.37; and O, 3.57.
Example 17:
the fused heterocyclic compound 178 was synthesized as follows:
the preparation was carried out in substantially the same manner as in example 13, except that the compounds 13-a, 13-b and 13-d were replaced with the compounds 17-a, 17-b and 17-d in a yield of 81.5%, ESI-MS (M/z) (M +): theoretical 578.69, found 578.98, elemental analysis result (molecular formula C42H22D4N 2O): theoretical value C, 87.17; h, 5.22; n, 4.84; o, 2.76; found C, 87.17; h, 5.22; n, 4.84; o, 2.76.
Example 18:
the fused heterocyclic compound 184 is synthesized as follows:
the preparation was carried out in substantially the same manner as in example 13, except that the compounds 13-a, 13-b and 13-d were replaced with the compounds 18-a, 18-b and 18-d in a yield of 84.9%, ESI-MS (M/z) (M +): theoretical 690.88, found 691.03, elemental analysis result (molecular formula C49H26D9N 3O): theoretical value C, 85.19; h, 6.42; n, 6.08; o, 2.32; found C, 85.19; h, 6.42; n, 6.08; o, 2.32.
And (3) testing the material performance:
the fused heterocyclic compounds 1, 2, 5, 18, 19, 23, 41, 58, 64, 67, 81, 98, 104, 105, 149, 172, 178, 184 of examples 1 to 18 of the present invention were tested for glass transition temperature Tg and thermal weight loss temperature Td, and the results are shown in table 1:
note: the thermogravimetric analysis was carried out on a TGA N-1000 thermogravimetric analyzer at a temperature Td of 5% weight loss in a nitrogen atmosphere, the nitrogen flow rate was 10mL/min, the glass transition temperature Tg was measured by differential scanning calorimetry (DSC, New DSC N-650), and the temperature rise rate was 10 ℃/min.
Table 1:
as can be seen from table 1 above, the fused heterocyclic compound of the present invention has higher Td value and Tm value, which indicates that it has excellent thermal stability, and when it is applied to an organic electroluminescent device, the fused heterocyclic compound can effectively prolong the service life of the organic electroluminescent device, and can obtain better use effect.
Testing the performance of the device:
application example 1:
ITO is adopted as a reflecting layer anode substrate material, and water, acetone and N are sequentially used 2 Carrying out surface treatment on the glass substrate by plasma;
depositing HAT-CN with the thickness of 10nm to form a Hole Injection Layer (HIL) above the ITO anode substrate;
evaporating HT-1 with the thickness of 100nm above the Hole Injection Layer (HIL) to form a Hole Transport Layer (HTL);
evaporating EB-1 above the Hole Transport Layer (HTL) in vacuum to form an Electron Blocking Layer (EBL) with the thickness of 10 nm;
evaporating BH-1 serving as a blue light main body material and BD-1 serving as a blue light doping material (the dosage of BD-1 is 5% of ADN weight) at different rates to form a light-emitting layer with the thickness of 20nm on a Hole Transport Layer (HTL);
evaporating HB-1 onto the light-emitting layer to obtain a Hole Blocking Layer (HBL) with the thickness of 20 nm;
the fused heterocyclic compound 1 prepared in the embodiment 1 of the invention is used as an electron transport layer material (ET) to be evaporated on a Hole Blocking Layer (HBL) to obtain an Electron Transport Layer (ETL) with the thickness of 30nm, and LiQ with the thickness of 2nm is evaporated above the Electron Transport Layer (ETL) to form an Electron Injection Layer (EIL);
then magnesium (Mg) and silver (Ag) are mixed and evaporated in a ratio of 9:1 to obtain a cathode with the thickness of 15nm, DNTPD with the thickness of 50nm is deposited on the sealing layer of the cathode, and in addition, the surface of the cathode is sealed by UV hardening adhesive and sealing film (seal cap) containing a moisture remover so as to protect the organic electroluminescent device from being influenced by oxygen or moisture in the atmosphere, thus preparing the organic electroluminescent device.
Application examples 2 to 18
Organic electroluminescent devices of application examples 2 to 18 were produced by replacing the fused heterocyclic compound 1 in application example 1 with the fused heterocyclic compounds 2, 5, 18, 19, 23, 41, 58, 64, 67, 81, 98, 104, 105, 149, 172, 178, and 184 of examples 2 to 18 of the present invention, respectively, and the rest of the materials were the same as in application example 1.
Comparative examples 1 to 2
Comparative examples 1 to 2 and application example 1 were different in that ET-1 and ET-2 were used instead of the fused heterocyclic compound 1 in application example 1, respectively, and the rest was the same as in application example 1.
The organic electroluminescent devices prepared in application examples 1 to 18 and comparative examples 1 to 2 were respectively tested, and the test results are shown in table 2.
Table 2:
as can be seen from table 2, when the fused heterocyclic compound of the present invention is applied to an organic electroluminescent device and used as an Electron Transport Layer (ETL), the light emitting efficiency of the organic electroluminescent device can be greatly improved, the start voltage is reduced, and the power consumption of the device is relatively reduced.
The organic electroluminescent devices prepared in the comparative examples 1 to 2 and the application examples 1 to 5 were subjected to a light emission life test to obtain data of light emission life T97% (time for which the light emission luminance was decreased to 97% of the initial luminance), and the test apparatus was a TEO light emitting device life test system. The results are shown in Table 3:
table 3:
as can be seen from table 3 above, when the fused heterocyclic compound of the present invention is applied to an organic electroluminescent device as an Electron Transport Layer (ETL), the service life of the prepared organic electroluminescent device is greatly prolonged, and thus the fused heterocyclic compound has a broad application prospect.
Claims (4)
1. A fused heterocyclic compound characterized by being any one of the following compounds:
2. an organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein the organic layer contains the fused heterocyclic compound according to claim 1.
3. The organic electroluminescent device according to claim 2, wherein the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer; at least one of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer, and the electron injection layer contains the fused heterocyclic compound according to claim 1.
4. The organic electroluminescent device according to claim 3, wherein the electron transport layer contains the fused heterocyclic compound according to claim 1.
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