CN116332962A - Arylamine compound and display substrate - Google Patents
Arylamine compound and display substrate Download PDFInfo
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- CN116332962A CN116332962A CN202310318489.6A CN202310318489A CN116332962A CN 116332962 A CN116332962 A CN 116332962A CN 202310318489 A CN202310318489 A CN 202310318489A CN 116332962 A CN116332962 A CN 116332962A
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- 239000000758 substrate Substances 0.000 title claims abstract description 70
- -1 Arylamine compound Chemical class 0.000 title claims abstract description 69
- 239000000463 material Substances 0.000 claims abstract description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 34
- 230000031700 light absorption Effects 0.000 claims abstract description 14
- 125000001424 substituent group Chemical group 0.000 claims abstract description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000006755 (C2-C20) alkyl group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 9
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 238000002835 absorbance Methods 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 125000006835 (C6-C20) arylene group Chemical group 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- 238000001704 evaporation Methods 0.000 abstract description 25
- 238000000034 method Methods 0.000 abstract description 18
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- 230000010287 polarization Effects 0.000 abstract description 7
- 125000005842 heteroatom Chemical group 0.000 abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 4
- 125000005264 aryl amine group Chemical group 0.000 abstract description 3
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- 238000003786 synthesis reaction Methods 0.000 description 8
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- YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical compound C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 description 7
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 6
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 5
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 3
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides an arylamine compound and a display substrate, wherein the arylamine compound has a structural formula shown in the following formula I; wherein the meanings of each group and substituent are the same as in the specification. The arylamine compound provided by the invention forms conjugation with benzene ring based on N of an arylamine structure, and increases the thermal stability of molecules, thereby ensuring the stability of a material evaporation process. Based on the introduction of hetero atoms, the polarization rate of molecules is greatly improved, and meanwhile, the space between heterocycle and benzene ring is close to a planar structure, so that the conjugation of the molecules is improved, the polarization rate is further increased, and the refractive index is extremely high; and, improve the materialThe ultraviolet light absorption performance improves the protection effect on the device.
Description
Technical Field
The invention relates to the technical field of display, in particular to an arylamine compound and a display substrate.
Background
The display screen nowadays is continuously developed towards the directions of high pixels, large color gamut and low power consumption, and the flexible display screen has obvious advantages compared with the traditional rigid display screen, and becomes an important technology in the field of display screens.
The current flexible display device mostly adopts a top emission device structure, and adopts a reflective anode and a transparent cathode to enhance the light-emitting efficiency through microcavity effect. In this device, one very important functional layer is the cap layer. The covering layer is positioned on the upper layer of the cathode and has a higher refractive index, and the covering layer and the cathode form a match of high and low refractive indexes, so that a better light emitting effect is realized.
The existing coating layer has lower refractive index at 460nm wavelength, so that the effect of improving the light extraction rate and the device efficiency is poor; and the light absorption coefficient at the wavelength of 400nm is lower, the ultraviolet light absorption to the external environment is smaller, and the device cannot be protected.
Disclosure of Invention
In view of the above, the present invention is directed to an arylamine compound and a display substrate, so as to solve the problems of poor effect of improving light extraction rate and protecting devices caused by lower refractive index at 460nm wavelength and lower light absorption coefficient at 400nm wavelength of the current flexible display device cover layer.
In order to achieve the above purpose, the technical scheme of the invention is realized as follows:
an arylamine compound having a structural formula shown in the following formula I:
wherein X is 1 、X 2 Each independently selected from O or S;
y is selected from O, S or N;
L 1 、L 2 and L 3 Each independently selected from any one of a single bond, a substituted or unsubstituted C2-C20 alkyl group, a substituted or unsubstituted C6-C20 arylene group, and a substituted or unsubstituted C5-C30 heteroarylene group;
the A ring and the B ring are respectively and independently selected from the following groups: a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group; or, the a ring and/or the B ring are absent;
at said L 1 Said L 2 Or said L 3 In the case where a substituent is present, the substituent is: hydrogen, deuterium, C2-C20 alkyl, C6-C20 aryl or C5-C20 heteroaryl;
in the case where a substituent is present on the a ring and the B ring, the substituent is: hydrogen, deuterium, C2-C20 alkyl, C6-C20 aryl or C5-C20 heteroaryl.
In an alternative embodiment, where Y is N, the Y further comprises an R group, the R group being attached to N;
wherein the R group is selected from the following groups: phenyl, biphenyl or naphthyl.
In an alternative embodiment, the a ring is a benzene ring or is absent; the B ring is benzene ring or is absent.
In an alternative embodiment, where X1 is O, X2 is O;
in the case where X1 is S, X2 is S.
In an alternative embodiment, Y is O or S.
In an alternative embodiment, where the L1 is phenylene, the L2 is a single bond, phenylene, or biphenyl;
and L3 is a single bond or phenylene.
In an alternative embodiment, the arylamine compound has a specific structural formula:
in an alternative embodiment, the arylamine compound has a refractive index of greater than or equal to 2.1 at a wavelength of 460 nm;
the refractive index of the arylamine compound at the wavelength of 530nm is more than or equal to 1.93;
the arylamine compound has a refractive index of 1.85 or more at a wavelength of 620 nm.
In an alternative embodiment, the arylamine compound has an absorbance of greater than or equal to 0.62 at a wavelength of 400 nm;
the light absorption coefficient of the arylamine compound at the wavelength of 450nm and the wavelength of more than 450nm is more than or equal to 0.
Compared with the prior art, the arylamine compound has the following advantages:
the arylamine compound provided by the invention forms conjugation with benzene ring based on N of an arylamine structure, and increases the thermal stability of molecules, thereby ensuring the evaporation process of the material. Based on the introduction of hetero atoms, the polarization rate of molecules is greatly improved, and meanwhile, the space between heterocycle and benzene ring is close to a planar structure, so that the conjugation of the molecules is improved, the polarization rate is further increased, and the refractive index is extremely high; and the ultraviolet light absorption performance of the material is improved, and the purpose of protecting the device is achieved.
Another objective of the present invention is to provide a display substrate, so as to solve the problem that the existing flexible display device cover layer has a lower refractive index at 460nm wavelength and a lower light absorption coefficient at 400nm wavelength, resulting in poor effect of improving light extraction rate and protecting device.
In order to achieve the above purpose, the technical scheme of the invention is realized as follows:
a display substrate, comprising:
a substrate, and a light emitting device layer on the substrate;
the covering layer is positioned on one side of the light-emitting device layer, which is away from the substrate;
wherein the material of the covering layer comprises any one of the aromatic amine compounds.
In an alternative embodiment, the light emitting device layer includes a cathode layer, an anode layer, and an electroluminescent unit between the cathode layer and the anode layer;
wherein the anode layer is arranged close to the substrate, and the cathode layer is arranged far away from the substrate;
the cover layer is positioned on one side of the cathode layer away from the substrate.
The display substrate and the arylamine compound have the same advantages as those of the prior art, and are not described herein.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the invention. In the drawings:
FIG. 1 shows electrostatic potential diagrams of arylamine compounds provided in examples of the present invention and comparative example compounds;
fig. 2 is a schematic diagram of a display substrate according to a second embodiment of the invention;
reference numerals:
101-a substrate; 102-a light emitting device layer; 103-a cover layer; 104-an anode layer; 105-cathode layer; 106-an electroluminescent unit.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and fully with reference to the accompanying drawings, in which it is evident that the embodiments described are some, but not all embodiments of the invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
It should be noted that the embodiments of the present invention and the features of the embodiments may be combined with each other without collision.
Example 1
The embodiment of the invention provides an arylamine compound, which has a structural formula shown in the following formula I:
wherein X1 and X2 are respectively and independently selected from O or S;
y is selected from N, O, S or Er;
l1, L2 and L3 are each independently selected from any one of a single bond, a substituted or unsubstituted C2-C20 alkyl group, a substituted or unsubstituted C6-C20 arylene group and a substituted or unsubstituted C5-C30 heteroarylene group;
the A ring and the B ring are respectively and independently selected from the following groups: a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group; or, the a ring and/or the B ring are absent;
in the case where a substituent is present for L1, L2 or L3, the substituent is: hydrogen, deuterium, C2-C20 alkyl, C6-C20 aryl or C5-C20 heteroaryl;
in the case where a substituent is present on the a ring and the B ring, the substituent is: hydrogen, deuterium, C2-C20 alkyl, C6-C20 aryl or C5-C20 heteroaryl.
In one embodiment, the a-ring and the B-ring are independently selected to be present or absent.
The term "hetero" as used in heteroaryl means that at least one carbon atom in the aromatic ring is substituted with a heteroatom selected from any one or more of nitrogen atom (N), oxygen atom (O) and sulfur atom (S).
The arylamine compound provided by the embodiment of the invention forms conjugation with benzene ring based on N of an arylamine structure, and increases the thermal stability of molecules, thereby ensuring the evaporation process of the material. Based on the introduction of hetero atoms, the polarization rate of molecules is greatly improved, and meanwhile, the space between heterocycle and benzene ring is close to a planar structure, so that the conjugation of the molecules is improved, the polarization rate is further increased, and the refractive index is extremely high; and the ultraviolet light absorption performance of the material is improved, and the purpose of protecting the device is achieved.
In an alternative embodiment, where Y is N, the Y further comprises an R group, the R group being attached to N;
wherein the R group is selected from the following groups: phenyl, biphenyl or naphthyl.
In an alternative embodiment, the a ring is a benzene ring or is absent; the B ring is benzene ring or is absent.
In an alternative embodiment, where X1 is O, X2 is O;
in the case where X1 is S, X2 is S.
In an alternative embodiment, Y is O or S.
In an alternative embodiment, where the L1 is phenylene, the L2 is a single bond, phenylene, or biphenyl;
and L3 is a single bond or phenylene.
In an alternative embodiment, the arylamine compound has a specific structural formula:
in an alternative embodiment, the arylamine compound has a refractive index of greater than or equal to 2.1 at a wavelength of 460 nm;
the refractive index of the arylamine compound at the wavelength of 530nm is more than or equal to 1.93;
the refractive index of the arylamine compound at the wavelength of 620nm is more than or equal to 1.85.
In an alternative embodiment, the arylamine compound has an absorbance of greater than or equal to 0.62 at a wavelength of 400 nm;
the light absorption coefficient of the arylamine compound at the wavelength of 450nm and the wavelength of more than 450nm is more than or equal to 0.
The following are synthetic procedures and performance test data for arylamine compounds according to some exemplary embodiments of the invention:
synthesis example 1
Synthesis of Compound 1:
1.75g of 7.5mmol of benzonaphthofuran-3-amino solution, 4.11g of 15mmol of 2- (4-bromophenyl) -furan pyridine solution, 6.22g of 45mmol of K2CO3 solution, and 150mL of toluene solution were added to a 0.5L reaction flask under nitrogen atmosphere, and the mixture was sufficiently stirred.
0.17g of a 0.15mmol catalyst Pd (PPh 3) 4 solution and 25mL of distilled water were added thereto, and the reaction was stirred for 10 hours to allow the reaction to proceed sufficiently when the temperature in the reaction apparatus was raised to a liquid reflux.
Then 35mL of distilled water was added to terminate the reaction. After cooling, the organic solvent was distilled off under reduced pressure by filtration to give compound 1.
The yield of compound 1 can reach 76.2%.
Performance test data for compound 1:
mass spectrum m/z:619.7, element content (%): c (C) 42 H 25 N 3 O 3 ，C，81.41；H，4.07；N，6.78；O，7.75；
1H NMR：8.43-8.03(5H)，7.8-7.69(3H)，7.63-7.42(6H)，7.37-7.21(8H)，6.91-6.56(3H)。
Synthesis example 2
Synthesis of Compound 4:
1.88g of 7.5mmol of benzonaphthothiophene-3-amino solution, 4.11g of 15mmol of 2- (4-bromophenyl) -furan pyridine solution, 6.22g of 45mmol of K2CO3 solution, and 150mL of toluene solvent were added to a 0.5L reaction flask under nitrogen atmosphere, and the mixture was sufficiently stirred.
0.17g of a 0.15mmol catalyst Pd (PPh 3) 4 solution and 25mL of distilled water were added thereto, and the reaction was stirred for 10 hours to allow the reaction to proceed sufficiently when the temperature in the reaction apparatus was raised to a liquid reflux.
Then 35mL of distilled water was added to complete the reaction. After cooling, the organic solvent was distilled off under reduced pressure by filtration to give compound 4.
The yield of compound 4 can reach 74.1%.
Performance test data for compound 4:
mass spectrum m/z:635.17, element content (%): c (C) 42 H 25 N 3 O 2 S，C，79.35；H，3.96；N，6.61；O，5.03；S，5.04；
1H NMR：8.43-8.01(5H)，7.86-7.69(4H)，7.64-7.43(6H)，7.37-7.33(6H)，7.21-6.56(4H)。
Synthesis example 3
Synthesis of Compound 13:
1.75g of a 7.5mmol solution of benzonaphthofuran-3-amino, 4.35g of a 15mmol solution of 2- (4-bromophenyl) -thiophenopyridine, 6.22g of a 45mmol solution of K2CO3, and 150mL of toluene solvent were placed in a 0.5L reaction flask under nitrogen atmosphere and stirred well.
0.17g of a 0.15mmol catalyst Pd (PPh 3) 4 solution and 25mL of distilled water were added thereto, and the reaction was stirred for 10 hours to allow them to react sufficiently when the temperature in the reaction apparatus was raised to a liquid reflux.
Then 35mL of distilled water was added to complete the reaction. After cooling, the organic solvent was distilled off under reduced pressure by filtration to obtain compound 13.
The yield of compound 13 can reach 76.2%.
Performance test data for compound 13:
mass spectrum m/z:651.14, element content (%): c (C) 42 H 25 N 3 OS 2 ，C，77.39；H，3.87；N，6.45；O，2.45；S，9.84；
1H NMR：8.43-8.03(5H)，7.8-7.69(5H)，7.49-7.42(2H)，7.37-7.36(6H)，7.1-6.91(7H)。
The synthesis of other compounds provided in the embodiments of the present invention may be realized based on the synthesis process of the above compound 1, compound 4 and compound 13.
The performance test of the arylamine compounds and the comparative compounds provided in the examples of the present invention is described in detail below.
Wherein, the compounds used as comparison are the following compounds:
the arylamine compounds provided by the embodiment of the invention contain at least two pyridofuran and/or pyridothiophene structures, and based on the two structures, a better conjugation effect and a planar structure are achieved, so that the molecular polarization rate is greatly improved, and the refractive index is further greatly improved.
Referring to table 1, table 1 shows the dihedral angles at which the pyridofuran structure and the pyridothiophene structure of the arylamine compound provided by the example of the present invention are respectively connected to the benzene ring, and the dihedral angles at which the phenyl structure and the benzoxazole structure of the comparative example compound are respectively connected to the benzene ring.
TABLE 1
As shown in Table 1, the phenyl structure of the comparative example compound had a larger dihedral angle when it was linked to the benzene ring, which indicated that the conjugation was poor. The dihedral angles of the pyridofuran structure and the pyridothiophene structure of the arylamine compound provided by the embodiment of the invention are smaller and approach to 0, and the structure approaches to a planar structure, so that the arylamine compound has better conjugation.
The benzoxazole structure of the comparative example compound has a lower polarizability due to the NO five-membered heterocycle in the benzoxazole structure, although the dihedral angle is smaller when it is connected to the benzene ring.
The pyridofuran structure and the N atom in the pyridothiophene structure of the arylamine compound provided by the embodiment of the invention are positioned on the benzene ring, so that the electron delocalization in the group is stronger, and the polarizability is higher.
Referring to fig. 1, fig. 1 shows electrostatic potential diagrams of an arylamine compound provided by an embodiment of the present invention and a comparative example compound, as shown in fig. 1, wherein a in fig. 1 is an electrostatic potential diagram when a pyridofuran structure of the arylamine compound provided by an embodiment of the present invention is connected to a benzene ring; b is an electrostatic potential diagram of the benzoxazole structure of the comparative compound when connected to the benzene ring; c is an electrostatic potential diagram of the phenyl structure of the comparative example compound when it is linked to the benzene ring.
At the wavelength of 460nm, the refractive index of the pyridofuran structure of the arylamine compound provided by the embodiment of the invention when connected with the benzene ring is 1.77; the refractive index of the benzoxazole structure of the comparative compound when attached to the benzene ring was 1.74; the refractive index of the phenyl structure of the comparative example compound when it was linked to the benzene ring was 1.73.
It can be seen that the refractive index of the pyridofuran structure of the arylamine compound provided by the embodiment of the invention is obviously higher than the refractive index of the benzoxazole structure of the comparative example compound and the refractive index of the phenyl structure of the comparative example compound.
Referring to table 2, table 2 shows a comparison table of refractive indices between some example compounds among the arylamine compounds provided in the examples of the present invention and the comparative example compounds.
TABLE 2
As shown in Table 2, the refractive index of the arylamine compound provided by the embodiment of the invention at the wavelength of 460nm is more than or equal to 2.1; a refractive index at a wavelength of 530nm of greater than or equal to 1.93; the refractive index at a wavelength of 620nm is greater than or equal to 1.85.
Compared with the compound of the comparative example, the arylamine compound provided by the embodiment of the invention has higher refractive indexes at the wavelength of 460nm, the wavelength of 530nm and the wavelength of 620 nm.
Referring to table 3, table 3 shows a table of absorbance coefficients and glass transition temperatures between arylamine compounds and comparative example compounds provided in examples of the present invention.
TABLE 3 Table 3
The glass transition temperature Tg refers to the temperature of the material from a glass state to a high-elastic state, and is an important parameter for ensuring the material to be stable all the time in the evaporation process. The glass transition temperature Tg determines the thermal stability of the material in evaporation, and the higher the Tg is, the better the thermal stability of the material is.
In one embodiment, the glass transition temperature is measured by differential scanning calorimetry (Diffevential Scanning Calovimltry, DSC) and the second temperature increase is selected during the measurement and is from room temperature to 300 ℃.
As shown in Table 3, the light absorption coefficient of the arylamine compound provided by the embodiment of the invention at the wavelength of 400nm is more than or equal to 0.62; the absorbance is greater than or equal to 0 at wavelengths of 450nm and greater than 450 nm.
Compared with the compound of the comparative example, the arylamine compound provided by the embodiment of the invention has higher light absorption coefficient at the wavelength of 400nm, and the light absorption coefficient at the wavelength of 450nm is more than or equal to 0, so that the arylamine compound has better ultraviolet light absorption effect and better device protection effect.
In addition, the arylamine compound provided by the embodiment of the invention has higher glass transition temperature Tg, which indicates that the arylamine compound has good stability in an evaporation process. Therefore, the arylamine compound provided by the embodiment of the invention is suitable for being used as a light extraction material, can solve the problem of more decomposed impurities caused by unstable materials due to heating in an evaporation process, and is beneficial to improving the stability of the materials in devices and prolonging the service lives of the devices.
Example two
Referring to fig. 2, fig. 2 shows a schematic structural diagram of a display substrate according to a second embodiment of the present invention, and as shown in fig. 2, the display substrate includes:
a substrate 101 and a light emitting device layer 102 on the substrate 101;
a cover layer 103 on a side of the light emitting device layer 102 facing away from the substrate 101;
the material of the cover layer 103 includes any of the arylamine compounds described in any of the embodiments.
Wherein the light emitting device layer 102 may be an OLED light emitting device, in particular, comprising an anode layer 104, a cathode layer 105, and an electroluminescent unit 106 between the cathode layer 105 and the anode layer 104;
wherein the anode layer 104 is disposed close to the substrate 101, and the cathode layer 105 is disposed far from the substrate 101;
the cover layer 103 is located on the side of the cathode layer 105 remote from the substrate 101.
The preparation and testing of the display substrate provided by the embodiments of the present invention are described in detail below with an example.
Preparation of display substrate D1:
d1-1: preparing a substrate, cleaning and drying.
D1-2: and sequentially evaporating a hole injection layer HIL material, a hole transport layer HTL material and an electron blocking layer EBL material on the anode.
D1-3: sequentially evaporating a luminescent layer material on the electron blocking layer EBL, wherein the luminescent layer material comprises the following components: a blue host material and a blue dopant material.
D1-4: and evaporating a hole blocking layer HBL material, an electron transport layer ETL material and an electron injection layer EIL material on the light-emitting layer.
D1-5: and evaporating a cathode on the electron injection layer EIL.
D1-6: a capping layer is deposited over the cathode.
The material used for evaporating the coating layer of the display substrate D1 is the compound 1 provided by the embodiment of the invention, and the evaporating thickness is 65nm.
The thickness of the hole injection layer HIL of the obtained display substrate is 10nm, the thickness of the hole transport layer HTL is 110nm, the thickness of the electron blocking layer EBL is 5nm, the thickness of the luminescent layer is 20nm, the thickness of the hole blocking layer HBL is 5nm, the thickness of the electron transport layer is 30nm, the thickness of the electron injection layer EIL is 1nm, and the thickness of the cover layer CPL is 65nm.
Wherein the volume ratio of the blue light doping agent material in the light-emitting layer is 3%, and the volume ratio of the 8-hydroxyquinoline LIQ material in the electron transport layer is 50%.
Between the electron injection layer EIL and the capping layer CPL, there is a dielectric layer composed of magnesium Mg and silver Ag, the thickness of which is 13nm.
Preparation of display substrate D2:
the preparation process of the display substrate D2 is the same as that of the display substrate D1, and will not be described herein.
The material used for evaporating the coating layer of the display substrate D2 is the compound 4 provided by the embodiment of the invention, and the evaporating thickness is 65nm.
Preparation of display substrate D3:
the preparation process of the display substrate D3 is the same as that of the display substrate D1, and will not be described herein.
The material used for evaporating the coating layer of the display substrate D3 is the compound 8 provided by the embodiment of the invention, and the evaporating thickness is 65nm.
Preparation of comparative example substrate R1:
the preparation process of the comparative example substrate R1 is the same as that of the display substrate D1 described above, and a detailed description thereof will be omitted.
The material used for evaporating the coating layer of the comparative example substrate R1 was comparative example compound CP-1, and the evaporating thickness was 65nm.
Preparation of comparative example substrate R2:
the preparation process of the comparative example substrate R2 is the same as that of the display substrate D1 described above, and will not be described here.
The material used for evaporating the coating layer of the comparative example substrate R2 is comparative example compound CP-2, and the evaporating thickness is 65nm.
Preparation of comparative example substrate R3:
the preparation process of the comparative example substrate R3 is the same as that of the display substrate D1 described above, and a detailed description thereof will be omitted.
The material used for evaporating the coating layer of the comparative example substrate R3 is comparative example compound CP-3, and the evaporating thickness is 65nm.
Preparation of comparative example substrate R4:
the preparation process of the comparative example substrate R4 is the same as that of the display substrate D1 described above, and a detailed description thereof will be omitted.
The material used for evaporating the coating layer of the comparative example substrate R4 is comparative example compound CP-4, and the evaporating thickness is 65nm.
Referring to table 4, table 4 shows a performance test comparative table between the display substrates D1 to D3 and the comparative example substrates R1 to R4 provided in the examples of the present invention.
| Display substrate | Cover layer material | Voltage (V) | Efficiency (cd/A) | Lifetime (h) |
| D1 | Compound 1 | 98％ | 106％ | 104％ |
| D2 | Compound 4 | 98％ | 107％ | 105％ |
| D3 | Compound 8 | 99％ | 104％ | 101％ |
| Comparative example R1 | Comparative example CP-1 | 100％ | 100％ | 100％ |
| Comparative example R2 | Comparative example CP-2 | 100％ | 101％ | 100％ |
| Comparative example R3 | Comparative example CP-3 | 100％ | 102％ | 100％ |
| Comparative example R4 | Comparative example CP-4 | 99％ | 103％ | 100％ |
TABLE 4 Table 4
As shown in table 4, in the case where the thicknesses of the cover layer materials are the same, the refractive indexes of the cover layers of the display substrates D1 to D3 provided by the embodiments of the present invention are higher, so that more light can be extracted from the top emission device, and thus the efficiency of the display substrate is higher. Due to the increase of the efficiency of the display substrate, when the same brightness is achieved, the voltage of the display substrates D1 to D3 provided by the embodiment of the invention is lower, and the service life is longer.
Referring to table 5, table 5 shows a structural diagram of materials used for other functional film layers of the display substrate according to the embodiment of the present invention.
TABLE 5
Although the embodiments of the present invention are described above, the embodiments are only used for facilitating understanding of the present invention, and are not intended to limit the present invention. Any person skilled in the art will recognize that any modifications or variations can be made in the form and detail of the present invention without departing from the spirit and scope of the invention as disclosed, but the scope of the invention is to be determined by the appended claims.
In this specification, each embodiment is described in a progressive manner, and each embodiment is mainly described by differences from other embodiments, and identical and similar parts between the embodiments are all enough to be referred to each other.
It will be apparent to those skilled in the art that embodiments of the present disclosure may be provided as a method, apparatus, or computer program product. Accordingly, the disclosed embodiments may take the form of an entirely hardware embodiment, an entirely software embodiment, or an embodiment combining software and hardware aspects. Furthermore, embodiments of the present disclosure may take the form of a computer program product on one or more computer-usable storage media (including, but not limited to, disk storage, CD-ROM, optical storage, etc.) having computer-usable program code embodied therein.
Embodiments of the present disclosure are described with reference to flowchart illustrations and/or block diagrams of methods, terminal devices (systems), and computer program products according to embodiments of the disclosure. It will be understood that each flow and/or block of the flowchart illustrations and/or block diagrams, and combinations of flows and/or blocks in the flowchart illustrations and/or block diagrams, can be implemented by computer program instructions. These computer program instructions may be provided to a processor of a general purpose computer, special purpose computer, embedded processor, or other programmable data processing terminal device to produce a machine, such that the instructions, which execute via the processor of the computer or other programmable data processing terminal device, create means for implementing the functions specified in the flowchart flow or flows and/or block diagram block or blocks.
These computer program instructions may also be stored in a computer-readable memory that can direct a computer or other programmable data processing apparatus to function in a particular manner, such that the instructions stored in the computer-readable memory produce an article of manufacture including instruction means which implement the function specified in the flowchart flow or flows and/or block diagram block or blocks.
These computer program instructions may also be loaded onto a computer or other programmable data processing apparatus to cause a series of operational steps to be performed on the computer or other programmable apparatus to produce a computer implemented process such that the instructions which execute on the computer or other programmable apparatus provide steps for implementing the functions specified in the flowchart flow or flows and/or block diagram block or blocks.
While the preferred embodiments of the disclosed embodiments have been described, additional variations and modifications in those embodiments may occur to those skilled in the art once they learn of the basic inventive concepts. It is therefore intended that the following claims be interpreted as including the preferred embodiment and all such alterations and modifications as fall within the scope of the disclosed embodiments.
Finally, it is further noted that relational terms such as first and second, and the like are used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Moreover, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or terminal that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or terminal. Without further limitation, an element defined by the phrase "comprising one … …" does not exclude the presence of other like elements in a process, method, article or terminal device comprising the element.
The foregoing has described in detail an arylamine compound and a display substrate provided by the present disclosure, and specific examples have been applied herein to illustrate the principles and embodiments of the present disclosure, and the above examples are only for aiding in understanding the methods of the present disclosure and the core ideas thereof; meanwhile, as one of ordinary skill in the art will have variations in the detailed description and the application scope in light of the ideas of the present disclosure, the present disclosure should not be construed as being limited to the above description.
Claims (11)
1. The arylamine compound is characterized by having a structural formula shown in the following formula I:
wherein X is 1 、X 2 Each independently selected from O or S;
y is selected from O, S or N;
L 1 、L 2 and L 3 Each independently selected from any one of a single bond, a substituted or unsubstituted C2-C20 alkyl group, a substituted or unsubstituted C6-C20 arylene group, and a substituted or unsubstituted C5-C30 heteroarylene group;
the A ring and the B ring are respectively and independently selected from the following groups: a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group; or, the a ring and/or the B ring are absent;
at said L 1 Said L 2 Or said L 3 In the case where a substituent is present, the substituent is: hydrogen, deuterium, C2-C20 alkyl, C6-C20 aryl or C5-C20 heteroaryl;
in the case where a substituent is present on the a ring and the B ring, the substituent is: hydrogen, deuterium, C2-C20 alkyl, C6-C20 aryl or C5-C20 heteroaryl.
2. The arylamine compound according to claim 1, wherein in the case where said Y is N, said Y further comprises an R group, said R group being linked to N;
wherein the R group is selected from the following groups: phenyl, biphenyl or naphthyl.
3. The arylamine compound according to claim 1, wherein said a ring is a benzene ring or is absent; the B ring is benzene ring or is absent.
4. The aromatic amine compound according to claim 1, wherein in said X 1 In the case of O, the X 2 Is O;
at said X 1 In the case of S, the X 2 S.
5. The arylamine compound according to claim 1, wherein said Y is O or S.
6. The arylamine compound according to claim 1, wherein, at said L 1 In the case of phenylene, the L 2 Is a single bond, phenylene or biphenyl group;
the L is 3 Is a single bond or phenylene.
7. The arylamine compound according to claim 1, wherein said arylamine compound has a specific structural formula:
8. the aromatic amine compound according to claim 1, wherein the aromatic amine compound has a refractive index of 2.1 or more at a wavelength of 460 nm;
the refractive index of the arylamine compound at the wavelength of 530nm is more than or equal to 1.93;
the refractive index of the arylamine compound at the wavelength of 620nm is more than or equal to 1.85.
9. The aromatic amine compound according to claim 1, wherein the aromatic amine compound has an absorbance coefficient at a wavelength of 400nm of 0.62 or more;
the light absorption coefficient of the arylamine compound at the wavelength of 450nm and the wavelength of more than 450nm is more than or equal to 0.
10. A display substrate, comprising:
a substrate, and a light emitting device layer on the substrate;
the covering layer is positioned on one side of the light-emitting device layer, which is away from the substrate;
wherein the material of the cover layer comprises the arylamine compound according to any one of claims 1-8.
11. The substrate of claim 10, wherein the light emitting device layer comprises a cathode layer, an anode layer, and an electroluminescent unit positioned between the cathode layer and the anode layer;
wherein the anode layer is arranged close to the substrate, and the cathode layer is arranged far away from the substrate;
the cover layer is positioned on one side of the cathode layer away from the substrate.
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