CN113980008A - Light extraction material, light-emitting device, display panel and display device - Google Patents

Light extraction material, light-emitting device, display panel and display device Download PDF

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CN113980008A
CN113980008A CN202111272005.6A CN202111272005A CN113980008A CN 113980008 A CN113980008 A CN 113980008A CN 202111272005 A CN202111272005 A CN 202111272005A CN 113980008 A CN113980008 A CN 113980008A
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unsubstituted
light extraction
extraction material
light
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张东旭
陈磊
陈雪芹
梁丙炎
王丹
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BOE Technology Group Co Ltd
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Abstract

The invention provides a light extraction material, a light emitting device, a display panel and a display device. The light extraction material includes: the triazine compound has a branched chain, and the branched chain has one or more of a benzo five-membered heterocyclic compound, a N-containing heterocycle, biphenyl and a condensed ring. In the light extraction material, one or more of a benzo five-membered heterocyclic compound, a heterocycle containing N, biphenyl and a condensed ring are arranged on a branched chain of a triazine compound, the combination of the triazine compound and a branched chain substituent group can improve the polarizability and the number of molecules per unit volume of the material, improve the refractive index of the material and optimize the absorptivity, and meanwhile, the glass transition temperature of the light extraction material is higher, so that the thermal stability of the material is increased, the luminous efficiency of a device is improved, and after the structure is optimized, the thermal stability of the material is increased, the stability of an evaporation process is also ensured, and the problem of service life of the device caused by impurities generated in the evaporation due to the instability of the material is solved.

Description

Light extraction material, light-emitting device, display panel and display device
Technical Field
The invention relates to the technical field of display, in particular to a light extraction material, a light emitting device, a display panel and a display device.
Background
The light extraction can be improved by adding a layer of high refractive index material on the translucent cathode, which layer is referred to as the light extraction layer. The light extraction layer is specifically an organic or inorganic transparent material with a high refractive index in the OLED, and the light emitting device with the light extraction layer can improve the light emitting mode, so that light originally limited in the device can be emitted out of the device, and higher light extraction efficiency is shown. The coupling efficiency of the traditional light taking-out material is low, so that the light-emitting device is low in efficiency and poor in thermal stability, and the coupling efficiency of the traditional light taking-out material cannot meet the requirements of high-efficiency and long-service-life devices required at present.
Disclosure of Invention
In view of the above, the present invention provides a light extraction material, a light emitting device, a display panel and a display apparatus, which are used to solve the problems of low coupling efficiency of the existing light extraction material, low efficiency of the light emitting device and poor thermal stability.
In order to solve the technical problems, the invention adopts the following technical scheme:
in a first aspect, a light extraction material according to an embodiment of the present invention includes:
the triazine compound has a branched chain, and the branched chain has one or more of a benzo five-membered heterocyclic compound, a N-containing heterocycle, biphenyl and a condensed ring.
Alternatively, the triazine compound has the formula:
Figure BDA0003329106570000021
wherein Ar1 and Ar2 can be the same or different, and Ar1 and Ar2 contain at least one structure of formula (II) and formula (III):
Figure BDA0003329106570000022
when Ar 1-Ar 7 are not in structures (II) or (III), Ar 1-Ar 7 are aryl of C6-C60, fused aryl of C10-C60 and five-membered or six-membered aromatic heterocycle of C5-C60;
x1 and X2 are CR2, O, N, NR2, or S;
y is C or N, wherein Y is not all C;
r1, R2 and R3 are hydrogen, deuterium, halogen, nitro, nitrile group, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 thioether, substituted or unsubstituted C6-C50 aryl, and substituted or unsubstituted C2-C50 heteroaryl formed by substituted or unsubstituted C2-C9 ring structure.
L1 and L2 are hydrogen, substituted or unsubstituted arylene of C6 to C50, and substituted or unsubstituted heteroaryl of C2 to C50.
Alternatively, adjacent two of Ar4 to Ar7 are connected to each other to form a six-membered ring, and at least one fused six-membered ring is present in the connected six-membered ring.
Optionally, the hydrogen on the six-membered ring is replaced by Ar3, Ar3 is halogen, nitro, nitrile, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 thioether, substituted or unsubstituted C6-C50 aryl, or substituted or unsubstituted C2-C50 heteroaryl formed by a substituted or unsubstituted C2-C9 ring structure.
Alternatively, the triazine compound has the formula:
Figure BDA0003329106570000031
wherein Ar1 and Ar2 contain at least one structure of formula (II) and formula (III):
Figure BDA0003329106570000032
when Ar 1-Ar 3 are not in structures (II) or (III), Ar 1-Ar 3 are aryl of C6-C60, fused aryl of C10-C60 and five-membered or six-membered aromatic heterocycle of C5-C60;
x1 and X2 are CR2, O, N, NR2, or S;
y is C or N, wherein Y is not all C;
r1, R2 and R3 are hydrogen, deuterium, halogen, nitro, nitrile group, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 thioether, substituted or unsubstituted C6-C50 aryl, and substituted or unsubstituted C2-C50 heteroaryl formed by substituted or unsubstituted C2-C9 ring structure.
L1 and L2 are hydrogen, substituted or unsubstituted arylene of C6 to C50, and substituted or unsubstituted heteroaryl of C2 to C50.
Alternatively, the triazine compound has the formula:
Figure BDA0003329106570000033
Figure BDA0003329106570000041
Figure BDA0003329106570000051
alternatively, the structural formula of (II) is:
Figure BDA0003329106570000052
Figure BDA0003329106570000061
alternatively, the structural formula of (III) is:
Figure BDA0003329106570000062
Figure BDA0003329106570000071
wherein the glass transition temperature of the light extraction material is 132 ℃ to 145 ℃.
Wherein the refractive index of the light extraction material at a wavelength of 460nm is 2.04-2.63; and/or
The refractive index of the light extraction material at the wavelength of 530nm is 1.98-2.45; and/or
The refractive index of the light extraction material at a wavelength of 620nm is 1.92-2.36.
In a second aspect, a light emitting device according to an embodiment of the present invention includes:
an anode, a light-emitting layer, and a cathode which are stacked;
a light extraction layer disposed on a side of the cathode away from the light emitting layer,
the light extraction layer includes the light extraction material described in the above embodiments.
In a third aspect, a display panel according to an embodiment of the present invention includes the light emitting device described in the above embodiment.
In a fourth aspect, a display device according to an embodiment of the present invention includes the display panel described in the above embodiment.
The technical scheme of the invention has the following beneficial effects:
the light extraction material of the embodiment of the present invention includes: the triazine compound has a branched chain, and the branched chain has one or more of a benzo five-membered heterocyclic compound, a N-containing heterocycle, biphenyl and a condensed ring. In the light extraction material, one or more of a benzo five-membered heterocyclic compound, a heterocycle containing N, biphenyl and a condensed ring are arranged on a branched chain of a triazine compound, the combination of the triazine compound and a branched chain substituent group can improve the polarizability and the number of molecules per unit volume of the material, improve the refractive index of the material and optimize the absorptivity, and meanwhile, the glass transition temperature of the light extraction material is higher, so that the thermal stability of the material is increased, the luminous efficiency of a device is improved, and after the structure is optimized, the thermal stability of the material is increased, the stability of an evaporation process is also ensured, and the problem of service life of the device caused by impurities generated in the evaporation due to the instability of the material is solved.
Drawings
FIG. 1 is a schematic view of a light-emitting device according to the present invention;
FIG. 2 is another schematic view of a light emitting device of the present invention;
fig. 3 is a schematic view of still another structure of the light emitting device of the present invention.
Reference numerals
An anode 10; a hole injection layer 11; a hole transport layer 12; an electron blocking layer 13;
a hole blocking layer 14; an electron transport layer 15; an electron injection layer 16;
a light-emitting layer 20;
a cathode 30;
a light extraction layer 40.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the drawings of the embodiments of the present invention. It is to be understood that the embodiments described are only a few embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the described embodiments of the invention, are within the scope of the invention.
The light extraction material of the embodiment of the present invention includes: the triazine compound has a branched chain, and the branched chain has one or more of a benzo five-membered heterocyclic compound, a N-containing heterocycle, biphenyl and a condensed ring. In the light extraction material provided by the embodiment of the invention, one or more of a benzo five-membered heterocyclic compound, a heterocyclic ring containing N, biphenyl and a condensed ring are arranged on a branched chain of a triazine compound, and the triazine compound is combined with a branched chain substituent to improve the polarizability and the number of molecules per unit volume of the material, improve the refractive index of the material and optimize the absorptivity. According to the invention, the triazine derivative and the conjugate group with high polarizability and large planarity are used as cores to ensure that the triazine derivative has high molecular polarizability, and the aza-benzene and/or benzo five-membered heterocycle is used as a branched chain to improve the polarizability and adjust the molecular spectrum at the same time, so that the absorption region is in an ultraviolet band, and the service life and efficiency of the device can be improved while the color coordinate of the device is not changed.
In some embodiments, the triazine compound may have a structural formula:
Figure BDA0003329106570000091
wherein Ar1 and Ar2 can be the same or different, and Ar1 and Ar2 contain at least one structure of formula (II) and formula (III):
Figure BDA0003329106570000092
when Ar 1-Ar 7 are not in structures (II) or (III), Ar 1-Ar 7 are aryl of C6-C60, fused aryl of C10-C60 and five-membered or six-membered aromatic heterocycle of C5-C60;
x1 and X2 are CR2, O, N, NR2, or S;
y is C or N, wherein Y is not all C;
r1, R2 and R3 are hydrogen, deuterium, halogen, nitro, nitrile group, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 thioether, substituted or unsubstituted C6-C50 aryl, and substituted or unsubstituted C2-C50 heteroaryl formed by substituted or unsubstituted C2-C9 ring structure.
L1 and L2 are hydrogen, substituted or unsubstituted arylene of C6 to C50, and substituted or unsubstituted heteroaryl of C2 to C50.
In other embodiments, two adjacent ones of Ar 4-Ar 7 are linked to each other to form a six-membered ring, and at least one fused six-membered ring is present in the linked six-membered ring.
In some embodiments, the hydrogen on the six-membered ring can be substituted with Ar3, Ar3 is a halogen, a nitro group, a nitrile group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 thioether group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group formed by a substituted or unsubstituted C2 to C9 ring structure.
In other embodiments, the triazine compound has the formula:
Figure BDA0003329106570000101
wherein Ar1 and Ar2 contain at least one structure of formula (II) and formula (III):
Figure BDA0003329106570000102
when Ar 1-Ar 3 are not in structures (II) or (III), Ar 1-Ar 3 are aryl of C6-C60, fused aryl of C10-C60 and five-membered or six-membered aromatic heterocycle of C5-C60;
x1 and X2 are CR2, O, N, NR2, or S;
y is C or N, wherein Y is not all C;
r1, R2 and R3 are hydrogen, deuterium, halogen, nitro, nitrile group, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 thioether, substituted or unsubstituted C6-C50 aryl, and substituted or unsubstituted C2-C50 heteroaryl formed by substituted or unsubstituted C2-C9 ring structure.
L1 and L2 are hydrogen, substituted or unsubstituted arylene of C6 to C50, and substituted or unsubstituted heteroaryl of C2 to C50. Structures (II) or (III) may be attached to the body via R1, L1 or R2, R3.
In an embodiment of the invention, the triazine compound has the structural formula:
Figure BDA0003329106570000103
Figure BDA0003329106570000111
Figure BDA0003329106570000121
alternatively, the structural formula of (II) is:
Figure BDA0003329106570000122
Figure BDA0003329106570000131
alternatively, the structural formula of (III) is:
Figure BDA0003329106570000132
Figure BDA0003329106570000141
in some embodiments of the invention, the structural formula of the triazine compound can be the following structure:
Figure BDA0003329106570000142
Figure BDA0003329106570000151
Figure BDA0003329106570000161
Figure BDA0003329106570000171
Figure BDA0003329106570000181
Figure BDA0003329106570000191
Figure BDA0003329106570000201
Figure BDA0003329106570000211
Figure BDA0003329106570000221
Figure BDA0003329106570000231
Figure BDA0003329106570000241
Figure BDA0003329106570000251
Figure BDA0003329106570000261
during application, one or more of the above-mentioned compounds may be selected to form a light extraction layer.
The synthesis of some of the specific compounds described above is described below.
Synthesis example one (synthesis of compound 13):
Figure BDA0003329106570000262
synthesis of intermediate a: in a 500mL three-necked flask, nitrogen gas was introduced, 0.08mol of the starting material 1, 4-dibromobenzene, 200mL of THF (tetrahydrofuran), 0.2mol of 4-pyridineboronic acid, 0.0016mol of tetrakis (triphenylphosphine) palladium (PdP4) were added, and they were mixed with stirring, followed by addition of 0.12mol of K2CO3The aqueous solution (2M) was heated to 80 ℃ and refluxed for 15 hours, and the reaction was completed by sampling the sample. Naturally cooling, extracting with 200ml dichloromethane, demixing, drying the extract with anhydrous sodium sulfate, filtering, rotary evaporating the filtrate, and purifying with silica gel column to obtain intermediate A with HPLC purity of 99.6% and yield of 85.3%.
Figure BDA0003329106570000271
Intermediate BThe synthesis of (2): in a 500mL three-necked flask, nitrogen was introduced, and 0.04mol of the starting 2-bromo-4, 6-dichloro-1, 3, 5-triazine, 300mL of DMF (N, N-dimethylformamide), 0.048mol of intermediate A, 0.0004mol of palladium acetate (Pd (OAc))2) Stirring, then adding 0.06mol of K3PO4Heating the aqueous solution to 130 ℃, refluxing and reacting for 10 hours, taking a sample, and completely reacting. Naturally cooling, adding water, filtering the mixture, drying in a vacuum drying oven, and purifying the obtained residue with a silica gel column to obtain a compound intermediate B; HPLC purity 99.7% yield 87.3%.
Figure BDA0003329106570000272
Synthesis of intermediate C1: in a 500mL three-necked flask, nitrogen gas was introduced, and 0.03mol of the starting material 3-chlorobenzo [ d ] was added]Naphtho [3,2-b ]]Heterocycle, 0.05mol of bis (valeryl) diboron, 0.0015 mol of potassium acetate (KOAc),300ml of 1, 4-dioxane, 0.00068mol of palladium dibenzylideneacetone (Pd (dba))2) And 0.00023mol of tricyclohexylphosphine (PCy)3) And stirring until the reaction is finished. Adding water and chloroform at room temperature for extraction, layering, drying, distilling, recrystallizing, naturally cooling, adding water, filtering the mixture, drying in a vacuum drying oven, and purifying the obtained residue with silica gel column to obtain compound intermediate C1; HPLC purity 99.6% yield 84.3%.
Figure BDA0003329106570000281
Synthesis of intermediate C2: in a 500mL three-necked flask, nitrogen gas was introduced, and 0.03mol of 2- (4-chlorophenyl) benzo [ d ] as a starting material was added][1,3]Oxaazacyclo-retainer slow, 0.05mol of bis-valeryl diboron, 0.0015 potassium acetate (KOAc),300ml of 1, 4-dioxane, 0.00068mol of palladium dibenzylideneacetone (Pd (dba))2) And 0.00023mol of tricyclohexylphosphine (PCy)3) And stirring until the reaction is finished. Adding water and chloroform at room temperature for extraction, layering, drying, distilling, and performing heavy condensationCrystallizing, naturally cooling, adding water, filtering the mixture, drying in a vacuum drying oven, and purifying the obtained residue with silica gel column to obtain compound intermediate C1; HPLC purity 99.7, yield 85%.
Figure BDA0003329106570000282
Synthesis of compound 13: introducing nitrogen into a 500mL three-necked flask, adding 0.02mol of each of the intermediate B, the intermediate C1 and the intermediate C2 into 300mL of a tetrahydroheterocyclic solution, adding 0.12mol of potassium carbonate aqueous solution and 0.0016mol of tetrakis (triphenylphosphine) palladium, heating to 150 ℃, stirring until the reaction is finished, refluxing for 24 hours, extracting with 400mL of dichloromethane, layering, drying the extract with anhydrous sodium sulfate, filtering, performing rotary evaporation on the filtrate, and purifying by a silica gel column to obtain a target product so as to obtain a compound 13, wherein the HPLC purity is 99.2, and the yield is 27.8%. Mass spectrum m/z: 643.20, element content (%): c43H25N5O2，C，80.23；H，3.91；N，10.88；O，4.97；1H NMR：7.25(2H)7.38(2H)7.42～7.69(4H)7.74～7.82(3H)7.96(6H)8.11～8.70(4H)9.24(H)。
Synthesis example two: (Synthesis of Compound 29)
Figure BDA0003329106570000291
The synthesis of compound 29 is similar to the synthesis of compound 13, the intermediate a is changed to 2- (4-bromophenyl) naphthalene; then, 3- (4-chlorophenyl) pyridine was synthesized into 3- [4- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl ] pyridine by the method described in Synthesis example one; the target product is obtained by extraction, delamination, filtration, rotary evaporation of the filtrate and purification by a silica gel column, the HPLC purity is 99.4 percent, and the yield is 32.7 percent.
Mass spectrum m/z: 652.23, element content (%): c46H28N4O，C，84.64；H，4.32；N，8.58；O，2.45；1H NMR：7.25(4H)7.38～7.59(2H)7.55～7.69(5H)7.75～7.82(3H)7.96(4H)7.99～8.28(3H)8.42～8.70(2H)9.24(H)。
Synthesis example three: (Synthesis of Compound 47)
Figure BDA0003329106570000292
Synthesis of Compound 47 in analogy to the Synthesis of Compound 29, 3- [4- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl]Pyridine to intermediate C2; the target product is obtained by extraction, delamination, filtration, rotary evaporation of the filtrate and purification through a silica gel column, with the HPLC purity of 99.7 percent and the yield of 33 percent. Mass spectrum m/z: 692.22, element content (%): c48H28N4O2，C，83.22；H，4.07；N，8.09；O，4.62；1H NMR：7.25(2H)7.38(3H)7.42～7.55(3H)7.6～7.69(3H)7.74(2H)7.75～7.82(3H)7.96(6H)7.99～8.28(6H)。
Synthesis example four: (Synthesis of Compound 52)
Figure BDA0003329106570000301
The synthesis of compound 52 is similar to the synthesis of compound 29, and the target product is obtained by extraction, delamination, filtration, rotary evaporation of filtrate and silica gel column purification, with HPLC purity of 99.3% and yield of 44%. Mass spectrum m/z: 683.20, element content (%): c45H25N5O3，C，79.05；H，3.69；N，10.24；O，7.02。1H NMR：7.38(4H)7.42～7.49(2H)7.69(1H)7.74(4H)7.75～7.76(2H)7.82(1H)7.96(8H)8.03～8.28(3H)。
The other compounds can also be synthesized according to the synthesis method, and the specific substances can be reasonably selected and adjusted according to actual conditions.
The performance test of the compound in the invention is as follows:
the refractive index is an important physical parameter of a CPL (light extraction layer) material, the light coupling efficiency of the light-emitting device is directly determined by the size of the refractive index, and the measurement of the refractive index can be carried out by an ellipsometer; the scanning range of the instrument is 245-1000 nm; the silicon wafer is used for evaporating a film, and the thickness of the material film can be 50 nm.
The results of the tests on the above-mentioned different compounds (light extraction materials) are shown in table 1 below.
TABLE 1 results of refractive index measurements for different compounds
Figure BDA0003329106570000302
Figure BDA0003329106570000311
As can be seen from the test results in Table 1, the light extraction material compounds according to the general formula of the present invention all exhibit a higher refractive index than the comparative compound, which is advantageous for improving the optical coupling efficiency and device efficiency of the device.
Measurement of glass transition temperature
The high and low glass transition temperature (Tg) determines the thermal stability of the material in evaporation, and the higher the Tg, the better the thermal stability of the material. The measuring instrument is a DSC differential scanning calorimeter; the test atmosphere is nitrogen, the heating rate is 10 ℃/min, and the temperature range is 50-300 ℃; the measured glass transition temperatures (Tg) are shown in table 2.
TABLE 2 glass transition temperature of light extraction materials
Compound (I) Tg(℃) Compound (I) Tg(℃)
Compound 1 132 Compound 29 137
Compound 2 136 Compound 33 136
Compound 3 137 Compound 47 134
Compound 8 133 Compound 52 139
Compound 11 135 Compound 54 138
Compound 13 132 Comparative Compound 1 130
Compound 20 136 Comparative Compound 2 125
From the test results in table 2, it can be seen that the light extraction material compounds according to the general formula of the present invention all exhibit a high glass transition temperature, which is advantageous for improving the thermodynamic stability of the material, and the material is not cracked and changed during the evaporation process, which is advantageous for maintaining a long life of the material during the evaporation process.
The light-emitting device is produced by using the light extraction material of the present invention, and the light-emitting device uses the following compounds:
Figure BDA0003329106570000321
the specific implementation mode is as follows:
(1) under a vacuum of 1X 10-5Depositing a thin film on a glass substrate containing Indium Tin Oxide (ITO) as an anode (film thickness: 100nm) by vacuum evaporation under Pa;
(2) then co-evaporating compounds F4TCNQ and m-MTDATA on the substrate to form a Hole Injection Layer (HIL) with a thickness of 10 nm;
(3) then, a compound m-MTDATA was deposited on the HIL as a Hole Transport Layer (HTL) to a thickness of 100 nm;
(4) evaporating compound CBP on the hole transport layer with the thickness of 10nm to be used as an electron blocking layer (B-Prime);
(5) BH and BD are co-evaporated on the B-prime film, a light-emitting layer with the film thickness of 20nm is formed, the concentration of BH in the light-emitting layer is 97%, and the concentration of BD is 3%;
(6) evaporating TPBi with the thickness of 5nm on the luminous layer as a Hole Blocking Layer (HBL);
(7) co-evaporating BCP and Liq on the HBL to gasify the two materials at the same rate to form an electron transport layer with a thickness of 30 m;
(8) evaporating metal Yb with the thickness of 1nm and metal cathode Mg: Ag with the thickness of 13nm on the electron transport layer;
(9) the light extraction material of the present invention was vapor-deposited on the cathode to form a light extraction layer (CPL) of 60 nm.
The element configuration of the organic EL element to be implemented is schematically shown as follows:
ITO/m-MTDATA:F4TCNQ(3％)10nm/m-MTDATA(100nm)/CBP(10nm)/BH:BD(3％)20nm/TPBI(5nm)/BCP:Liq(1：1)30nm/Yb(1nm)/Mg：Ag(13nm)/CPL(60nm)；
the same embodiment can be used to produce green and red devices by changing the light-emitting layer:
ITO/m-MTDATA:F4TCNQ(3％)10nm/m-MTDATA(100nm)/CBP(45nm)/GH:GD(10％)40nm/TPBI(5nm)/BCP:Liq(1：1)30nm/Yb(1nm)/Mg：Ag(13nm)/CPL(60nm)；
ITO/m-MTDATA:F4TCNQ(3％)10nm/m-MTDATA(100nm)/CBP(75nm)/RH:RD(3％)45nm/TPBI(5nm)/BCP:Liq(1：1)30nm/Yb(1nm)/Mg：Ag(13nm)/CPL(60nm)。
the light emitting device can be packaged by glass UV, if the material TFE is packaged, LiF or organic materials with low refractive index n less than or equal to 1.6 need to be evaporated on CPL.
Comparative example 1
An organic light-emitting device was fabricated in the same manner as the device embodiments described above, except that: when the light extraction layer was formed in comparative example 1, the preparation of a light extraction layer film was performed using Ref1(CP 1).
Comparative example 2
An organic light-emitting device was manufactured in the same manner as in comparative example 1, except that: when the light extraction layer was formed in comparative example 2, the preparation of a light extraction layer film was performed using Ref2(CP 2).
Examples
An organic light-emitting device was manufactured in the same manner as in comparative example 1, except that: when the light extraction layer was formed in the examples, the preparation of the light extraction layer was performed using the light extraction material compound in the present invention.
The test data of the light emitting device in the examples are shown in table 3 below:
table 3 test data of blue light emitting device in example
Figure BDA0003329106570000341
As can be seen from the data in the examples in table 3, the compounds of the present invention (with similar conclusions in green and red devices) have higher light coupling efficiency, higher EQE compared to both Ref1 and Ref2, and higher glass transition temperature, resulting in a somewhat increased lifetime of the device compared to the comparative examples.
In some embodiments, the glass transition temperature of the light extraction material is 132-145 ℃, and the higher glass transition temperature is beneficial to the stability of the material, so that the problem that impurities generated in evaporation due to the instability of the material influence the service life of the device is avoided.
In some embodiments, the light extraction material has a refractive index of 2.04-2.63 at a wavelength of 460 nm; and/or the refractive index of the light extraction material at the wavelength of 530nm is 1.98-2.45; and/or the refractive index of the light extraction material at a wavelength of 620nm is 1.92-2.36. The light extraction material has high refractive index, and the refractive index is high when the light extraction layer of the light-emitting device is prepared, so that light can be emitted easily, and the light-emitting efficiency of the device can be improved.
An embodiment of the present invention provides a light emitting device, as shown in fig. 1 to 3, including: an anode 10, a light-emitting layer 20, a cathode 30 and a light extraction layer 40 are stacked, wherein the light extraction layer 40 is disposed on the side of the cathode 30 far away from the light-emitting layer 20, and the light extraction layer 40 includes the light extraction material described in the above embodiments. The light extraction layer 40 has high refractive index and good thermal stability, and the light emitting device has low driving voltage, so that the light emitting efficiency of the device can be improved, and the problem of device service life caused by impurities generated in evaporation due to unstable materials is solved.
The light emitting device may further include: a hole injection layer 11, a hole transport layer 12, an electron blocking layer 13, an electron transport layer 15, and a hole blocking layer 14. The anode 10, the hole injection layer 11, the hole transport layer 12, the electron blocking layer 13, the light-emitting layer 20, the hole blocking layer 14, the electron transport layer 15, and the cathode 30 are stacked in this order. The light emitting device may further include: an electron injection layer 16, the electron injection layer 16 may be disposed between the electron transport layer 15 and the cathode 30.
An embodiment of the present invention provides a display panel including the light emitting device described in the above embodiment. The display panel with the light-emitting device in the embodiment of the invention has high light-emitting efficiency and long service life.
An embodiment of the present invention provides a display device, including the display panel described in the above embodiment. The display device with the display panel in the embodiment of the invention has high luminous efficiency and long service life.
Unless defined otherwise, technical or scientific terms used herein shall have the ordinary meaning as understood by one of ordinary skill in the art to which this invention belongs. The use of "first," "second," and similar terms in the present application do not denote any order, quantity, or importance, but rather the terms are used to distinguish one element from another. The terms "connected" or "coupled" and the like are not restricted to physical or mechanical connections, but may include electrical connections, whether direct or indirect. "upper", "lower", "left", "right", and the like are used merely to indicate relative positional relationships, and when the absolute position of the object being described is changed, the relative positional relationships are changed accordingly.
While the foregoing is directed to the preferred embodiment of the present invention, it will be understood by those skilled in the art that various changes and modifications may be made without departing from the spirit and scope of the invention as defined in the appended claims.

Claims (13)

1. A light extraction material, comprising:
the triazine compound has a branched chain, and the branched chain has one or more of a benzo five-membered heterocyclic compound, a N-containing heterocycle, biphenyl and a condensed ring.
2. A light extraction material according to claim 1, wherein the triazine compound has the formula:
Figure FDA0003329106560000011
wherein Ar1 and Ar2 can be the same or different, and Ar1 and Ar2 contain at least one structure of formula (II) and formula (III):
Figure FDA0003329106560000012
when Ar 1-Ar 7 are not in structures (II) or (III), Ar 1-Ar 7 are aryl of C6-C60, fused aryl of C10-C60 and five-membered or six-membered aromatic heterocycle of C5-C60;
x1 and X2 are CR2, O, N, NR2, or S;
y is C or N, wherein Y is not all C;
r1, R2 and R3 are hydrogen, deuterium, halogen, nitro, nitrile group, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 thioether, substituted or unsubstituted C6-C50 aryl, and substituted or unsubstituted C2-C50 heteroaryl formed by substituted or unsubstituted C2-C9 ring structure.
L1 and L2 are hydrogen, substituted or unsubstituted arylene of C6 to C50, and substituted or unsubstituted heteroaryl of C2 to C50.
3. A light extraction material according to claim 2, wherein adjacent two of Ar4 to Ar7 may be connected to each other to form a six-membered ring, and at least one fused six-membered ring is present in the connected six-membered ring.
4. A light extraction material as claimed in claim 3, wherein hydrogen on the six membered ring is substituted by Ar3, Ar3 is halogen, nitro, nitrile, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C1 to C30 thioether, substituted or unsubstituted C6 to C50 aryl, C2 to C50 heteroaryl formed by substituted or unsubstituted C2 to C9 ring structure.
5. A light extraction material according to claim 1, wherein the triazine compound has the formula:
Figure FDA0003329106560000021
wherein Ar1 and Ar2 contain at least one structure of formula (II) and formula (III):
Figure FDA0003329106560000022
when Ar 1-Ar 3 are not in structures (II) or (III), Ar 1-Ar 3 are aryl of C6-C60, fused aryl of C10-C60 and five-membered or six-membered aromatic heterocycle of C5-C60;
x1 and X2 are CR2, O, N, NR2, or S;
y is C or N, wherein Y is not all C;
r1, R2 and R3 are hydrogen, deuterium, halogen, nitro, nitrile group, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 thioether, substituted or unsubstituted C6-C50 aryl, and substituted or unsubstituted C2-C50 heteroaryl formed by substituted or unsubstituted C2-C9 ring structure.
L1 and L2 are hydrogen, substituted or unsubstituted arylene of C6 to C50, and substituted or unsubstituted heteroaryl of C2 to C50.
6. A light extraction material according to any one of claims 1 to 5, wherein the triazine compound has the formula:
Figure FDA0003329106560000031
Figure FDA0003329106560000041
7. a light extraction material according to any one of claims 2 to 5, wherein the formula of (II) is:
Figure FDA0003329106560000042
Figure FDA0003329106560000051
8. a light extraction material according to any one of claims 2 to 5, wherein the formula of (III) is:
Figure FDA0003329106560000052
Figure FDA0003329106560000061
9. a light extraction material according to claim 1, wherein the light extraction material has a glass transition temperature in the range of 132 ℃ to 145 ℃.
10. A light extraction material according to claim 1, wherein the refractive index of the light extraction material at a wavelength of 460nm is in the range 2.04-2.63; and/or
The refractive index of the light extraction material at the wavelength of 530nm is 1.98-2.45; and/or
The refractive index of the light extraction material at a wavelength of 620nm is 1.92-2.36.
11. A light emitting device, comprising:
an anode, a light-emitting layer, and a cathode which are stacked;
a light extraction layer disposed on a side of the cathode away from the light emitting layer,
the light extraction layer comprising the light extraction material of any one of claims 1-10.
12. A display panel comprising the light-emitting device according to claim 11.
13. A display device characterized by comprising the display panel described in claim 12.
CN202111272005.6A 2021-10-29 2021-10-29 Light extraction material, light-emitting device, display panel and display device Pending CN113980008A (en)

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