CN111341920A - Organic electroluminescent device - Google Patents

Organic electroluminescent device Download PDF

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CN111341920A
CN111341920A CN201811551549.4A CN201811551549A CN111341920A CN 111341920 A CN111341920 A CN 111341920A CN 201811551549 A CN201811551549 A CN 201811551549A CN 111341920 A CN111341920 A CN 111341920A
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terphenyl
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张艳
吴俊宇
孙龙
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Guan Eternal Material Technology Co Ltd
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Abstract

The invention provides an organic electroluminescent device which comprises a first electrode layer, a light-emitting layer, a second electrode layer and a light extraction layer arranged outside the second electrode layer, wherein the light extraction layer comprises any one of compounds A, B, C or D or a combination of at least two of compounds. The light extraction layer adopted by the invention utilizes the characteristic of high refractive index, can effectively promote light extraction, improves the efficiency of the device, and obviously improves the light extraction efficiency of the organic electroluminescent device obtained by the invention.

Description

Organic electroluminescent device
Technical Field
The invention belongs to the technical field of luminescent devices, relates to an organic electroluminescent device, and particularly relates to a light extraction layer in an organic electroluminescent top-emitting device.
Background
In recent years, Organic Light Emitting Diodes (OLEDs) have become very popular emerging flat panel display products due to their advantages of self-luminescence, high luminous efficiency, wide color gamut, low voltage, and the like.
In the OLED device, the main factors affecting the light extraction efficiency include the light emission efficiency of the light emitting layer, the light coupling efficiency in each functional layer, and the light extraction condition at each interface layer. In general, when light is incident from a high refractive index material to a low refractive index material, total reflection is likely to occur, which causes light transmitted through the cathode in the top emission device to be reflected back to the organic layer when the light exits at an angle greater than the critical angle, and a part of the light is absorbed, thereby reducing the light exit efficiency. Therefore, a light extraction layer, which is a material having a high refractive index, needs to be covered outside the cathode of the top emission device, and the light extraction layer has high requirements for material stability, film crystallinity, and light transmission (refractive index).
CN105118848A discloses an organic light emitting display device, which includes a transparent glass substrate, one side of the transparent glass substrate is in contact with air, and the other side is a light extraction layer; the light extraction layer is formed on the lower surface of the transparent glass and is used for transmitting light rays emitted by the light emitting layer to the transparent glass substrate; the first electrode layer is formed on the lower surface of the light extraction layer, and the surface of the first electrode layer is smooth; the light-emitting layer covers the lower surface of the first electrode layer and is used for emitting light; a second electrode layer formed on a lower surface of the light emitting layer, the first electrode layer and the second electrode layer sandwiching the light emitting layer; the light extraction layer is made of transparent materials and is in a sawtooth shape, and the light refractive index of the light extraction layer is larger than that of the light of the first electrode layer. The zinc oxide or titanium dioxide is used as a light extraction layer, so that the cost is high, and the light extraction efficiency is not high enough.
CN103022310A discloses a light extraction layer of an LED light emitting chip and an LED device, wherein the LED light emitting chip includes a semiconductor layer and a light extraction layer in direct contact with the semiconductor layer, a surface of the light extraction layer in direct contact with the semiconductor layer is a first surface, a surface of the light extraction layer in direct contact with an external medium is a second surface, a refractive index of the first surface is not less than a refractive index of the semiconductor layer, and the refractive index of the light extraction layer is in a decreasing trend from the first surface to the second surface, and the refractive index of the second surface is not greater than the refractive index of the external medium; the preparation method is complicated.
In order to more effectively promote light extraction and improve device efficiency, it is important to find a material with a higher refractive index for the light extraction layer.
Disclosure of Invention
The invention aims to provide an organic electroluminescent device.A light extraction layer adopted by the invention can more effectively promote light extraction and improve the efficiency of the device by utilizing the characteristic of high refractive index.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides an organic electroluminescent device comprising a first electrode layer, a light-emitting layer, a second electrode layer, and a light extraction layer disposed outside the second electrode layer, wherein a raw material for preparing the light extraction layer comprises any one of compounds A, B, C or D or a combination of at least two of compounds.
Wherein A has a structure shown in formula I:
Figure BDA0001910670960000011
Figure BDA0001910670960000021
wherein L independently represents one of a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C3-C30 heteroarylene; ra、RbThe same or different, each is independently selected from C1-C20 alkyl, C1-C20 alkenyl or C1-C20 alkynyl, RaAnd RbAre not connected with each other or are connected to form a ring structure; r is selected from one of C1-C20 alkyl, C1-C20 alkenyl, C1-C20 alkynyl, C1-C20 alkoxy, C6-C30 aryl and C3-C30 heteroaryl, and p is an integer of 0-7; ar is selected from heteroaryl represented by the general formula A, or substituted or unsubstituted aryl or heteroaryl of C6-C30 different from the general formula A, and the substituted groups are respectively and independently selected from halogen, alkyl of C1-C12, alkoxy of C1-C12, aryl of C6-C12, heteroaryl of C3-C12, cyano or hydroxyl;
Figure BDA0001910670960000022
in the formula A, L1Independently represent a single bond, a substituted or unsubstituted C6-C30 arylene, or a substituted or unsubstituted C3-C30 heteroarylene; "" denotes the attachment site to the parent nucleus; r1Selected from C1-C20 alkyl, C1-C20 alkenyl, C1-C20 alkynyl, C1-C20 alkoxy, C6-C30 aryl, C3-C30 heteroaryl, multiple R1Identical or different, two R in adjacent position1Are not connected with each other or are connected to form a ring; q is an integer from 0 to 7, preferably 0 or 1; x is selected from O, S, NR2、SiR3R4；R2Selected from C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl; r3、R4Each independently selected from C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl; the substituted groups are respectively and independently selected from halogen, C1-C12 alkyl, C1-C12 alkoxy, C6-C12 aryl, C3-C12 heteroaryl, cyano or hydroxyl, R3And R4Are not connected to each other or are connected to each other to form a ring.
The B has the structure as shown in the formula II;
Figure BDA0001910670960000023
wherein R is5Selected from the group consisting of substituted or unsubstituted aryl or fused ring aryl of C6-C30, substituted or unsubstituted heterocyclic aryl or fused ring heteroaryl of C3-C30; r6And R7Each independently selected from hydrogen, C1-C12 alkyl, C1-C8 alkoxy, C6-C30 substituted or unsubstituted aryl or fused ring aryl, C3-C30 substituted or unsubstituted heterocyclic aryl or fused ring heteroaryl; m and n are each independently selected from integers of 1 to 6; l isaSelected from single bond, or selected from C1-C12 alkyl, C1-C8 alkoxy, C5-C30 substituted or unsubstituted arylene, C3-C30 substituted or unsubstituted heterocyclic arylene; ar (Ar)1And Ar2Each independently selected from substituted or unsubstituted C6-C30 aryl or fused ring aryl; ar (Ar)3And Ar4Each independently selected from substituted or unsubstituted C6-C30 aryl or fused ring aryl, substituted or unsubstituted C3-C30 heterocyclic aryl or fused ring heteroaryl; the substituted groups are respectively and independently selected from halogen, C1-C10 alkyl or cycloalkyl, alkenyl, C1-C6 alkoxyOr thioalkoxy groups, monocyclic aromatic or fused ring aromatic hydrocarbon groups of C6-C30, monocyclic heteroaromatic or fused ring heteroaromatic hydrocarbon groups of C3-C30.
C has the structure as shown in formula III;
Figure BDA0001910670960000031
wherein R is8And R9Each independently selected from C1-C12 alkyl, C1-C8 alkoxy, C6-C30 substituted or unsubstituted aryl or fused ring aryl, C3-C30 substituted or unsubstituted heterocyclic aryl or fused ring heteroaryl, and R8And R9Are not connected with each other or are fused with each other to form a ring; r10And R11Each independently selected from H, C1-C12 alkyl, C1-C8 alkoxy, C6-C30 substituted or unsubstituted aryl or fused ring aryl, C3-C30 substituted or unsubstituted heterocyclic aryl or fused ring heteroaryl, or R10And R11In adjacent positions, R10And R11Fused to form a ring; r12Selected from H, substituted or unsubstituted aryl or fused ring aryl of C6-C30, substituted or unsubstituted heterocyclic aryl or fused ring heteroaryl of C3-C30; l isbSelected from single bond, or selected from C1-C12 alkyl, C1-C8 alkoxy, C3-C30 substituted or unsubstituted arylene or fused ring arylene, C3-C30 substituted or unsubstituted heterocyclylene aryl or fused ring heteroarylene; ar (Ar)5And Ar6Each independently selected from substituted or unsubstituted C6-C30 aryl or fused ring aryl, substituted or unsubstituted C3-C30 heterocyclic aryl or fused ring heteroaryl; the substituted groups are respectively and independently selected from halogen, alkyl or cycloalkyl of C1-C10, alkenyl, alkoxy or thioalkoxy groups of C1-C6, monocyclic aromatic hydrocarbon or fused ring aromatic hydrocarbon groups of C6-C30, and monocyclic aromatic hydrocarbon or fused ring aromatic hydrocarbon groups of C6-C30 containing a heteroatom selected from N, O, S, Si.
D has the structure as shown in formula IV;
Figure BDA0001910670960000032
wherein Ar is7、Ar8Each independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heterocyclic aryl; r13Selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl; k is an integer of 1 to 5; r14、R15Each independently selected from H, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C8 alkoxy, substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heterocyclic aryl, i and j are independently integers of 1-4, and the substituted groups are independently selected from halogen, C1-C10 alkyl or cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy or thioalkoxy groups, C6-C30 aryl or C3-C30 heterocyclic aryl.
i and j are each independently greater than 1, R14Two R's, which are identical or different, which are adjacent14Do not form a ring therebetween or form a ring by fusion, R15Two R's, which are identical or different, which are adjacent15Form no ring or form a ring by fusion.
Preferably, in the A compound, Ar is selected from heteroaryl represented by the general formula A, or condensed aryl or condensed heteroaryl having a large conjugated structure of C6-C30;
in the formula A, L1Represents a single bond or a substituted or unsubstituted C6-C12 arylene group, R1Selected from aryl of C6-C30, heteroaryl of C3-C30, q is 0 or 1, X is selected from NR2O or S; r2Is a substituted or unsubstituted C6-C30 aryl group;
the condensed aryl or condensed heteroaryl with a large conjugated structure of C6-C30 is selected from substituted or unsubstituted naphthyl, phenanthryl, benzophenanthryl, fluoranthenyl, anthracyl, pyrene, dihydropyrene, anise, perylene, fluoranthene, benzanthracene, triphenylene, tetracene, pentacene, benzopyrene, benzofuran, isobenzofuran, benzothiophene, isobenzothiophene, quinoline, isoquinoline, acridine, phenanthridine, benzopyrazole, pyridopyridine, benzo-5, 6-quinoline, benzo-6, 7-quinoline, benzo-7, 8-quinoline, phenothiazine, phenazine, indazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalimidazole, benzoxazole, naphthoxazole, anthraxazole, phenanthroizole, benzopyrazine, benzopyrimidine, quinoxaline, phenanthroline, phenanthroimidazole, benzopyrene, phenanthroiyl, etc, Phenazine, naphthyridine, azacarbazole, benzocarbazine, phenanthroline, benzotriazole, purine, pteridine, indolizine, benzothiadiazole, or a combination of these groups (the combination of these groups refers to a novel group in which at least two of the above groups are bonded to each other by a chemical bond).
Preferably, the general formula (A) is a group represented by the following general formula (A1),
Figure BDA0001910670960000041
wherein X is selected from N-Ph, O, S, R1Independently selected from aryl groups of C6-C12, r is 0 or 1, t is 0 or 1, and r and t are not simultaneously 1, Ph represents phenyl.
L1Represents a single bond or a substituted or unsubstituted phenylene group.
Preferably, in the compound B, Ar1And Ar2Each independently selected from phenyl or naphthyl.
Ar3And Ar4Each independently selected from phenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, phenanthryl, indenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9 '-dialkylfluorene, 9' -spirobifluorene, indenofluorene, fluoranthenyl, triphenylene, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, perylenyl,
Figure BDA0001910670960000042
A group, 1-tetracenyl, 2-tetracenyl, 9-tetracenyl, dibenzothiapyrrolyl, dibenzothienyl, dibenzofuranyl, dibenzoselenophenyl, carbazolyl or phenylcarbazolyl.
R5Selected from phenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, para-Terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, phenanthryl, indenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9 '-dialkylfluorene, 9' -spirobifluorene, indenofluorene, fluoranthenyl, triphenylene, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, perylenyl, etc,
Figure BDA0001910670960000043
A group, 1-tetracenyl, 2-tetracenyl, 9-tetracenyl, dibenzothiapyrrolyl, dibenzothienyl, dibenzofuranyl, dibenzoselenophenyl, carbazolyl or phenylcarbazolyl.
LaSelected from phenylene and naphthylene.
Preferably, in compound C, LbSelected from the group consisting of a single bond, phenyl, naphthyl, biphenyl, terphenyl, pyridyl, bipyridyl, pyrimidinyl, pyrrolyl, phenylpyridyl, pyrazinyl, quinolinyl, triazinyl, benzotriazinyl, benzoquinolinyl, dibenzopyrrolyl, carbazolyl, 9-phenylcarbazolyl, 9-naphthylcarbazolocarbazolyl, or dibenzocarbazolyl.
Ar5And Ar6Each independently selected from phenyl, anilino, 2-biphenyl, 3-biphenyl, 4-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, phenanthryl, indenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9 '-dialkylfluorene, 9' -spirobifluorene, indenofluorene, fluoranthenyl, triphenylene, 1-pyrenyl, triphenylene, etc, 2-pyrenyl, 4-pyrenyl, perylenyl,
Figure BDA0001910670960000052
A group, 1-tetracenyl, 2-tetracenyl, 9-tetracenyl, dibenzothiapyrrolyl, dibenzothienyl, dibenzofuranyl or dibenzoselenophenyl.
R8And R9Each independently selected from methyl, phenyl, biphenyl, naphthyl or fluorenyl, or R8And R9Fused to form a fluorene ring.
R10And R11Each independently selected from H, methyl, ethyl, phenyl, biphenyl, naphthyl, fluorenyl, spirofluorenyl, pyridyl, bipyridyl, pyrimidinyl, pyrrolyl, phenylpyridyl, pyrazinyl, quinolinyl, triazinyl, benzotriazolyl, benzopyrazinyl, benzoquinolinyl, dibenzopyrrolyl, carbazolyl, 9-phenylcarbazolyl, 9-naphthylcarbazolocarbazolyl or dibenzocarbazolyl, or R10And R11Fused to form an aryl group.
R12Selected from the group consisting of H, phenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, phenanthryl, indenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9 '-dialkylfluorene, 9' -spirobifluorene, indenofluorene, fluoranthenyl, triphenylene, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, perylenyl,
Figure BDA0001910670960000053
A group, 1-tetracenyl, 2-tetracenyl, 9-tetracenyl, dibenzothiapyrrolyl, dibenzothienyl, dibenzofuranyl or dibenzoselenophenyl.
Preferably, in the compound D, R13Selected from methyl, ethyl, propyl, cyclohexyl, phenyl, biphenyl, tolyl, 5-methyltetralin, naphthyl, benzofluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, terphenyl, anthracenyl, phenanthrenyl, pyrenyl or pyrenyl
Figure BDA0001910670960000054
And (4) a base.
R14、R15Each independently selected from H, methyl, ethyl, phenyl, biphenyl, naphthyl, fluorenyl, spirofluorenyl, pyridyl, bipyridyl, pyrimidyl, pyrrolyl, phenylpyridyl, pyrazineA phenyl group, a quinolyl group, a triazinyl group, a benzotriazinyl group, a benzopyrazinyl group, a benzoquinolyl group, a dibenzopyrrolyl group, a carbazolyl group, a 9-phenylcarbazolyl group, a 9-naphthylcarbazolocarbazolyl group or a dibenzocarbazolyl group.
Ar7、Ar8Each independently selected from the group consisting of phenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, phenanthryl, indenyl, benzofluorenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9 '-dialkylfluorene, 9' -spirobifluorenyl, indenofluorenyl, fluorenyl, triphenylene, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, perylenyl,
Figure BDA0001910670960000055
A group, 1-tetracenyl, 2-tetracenyl, 9-tetracenyl, dibenzothiapyrrolyl, dibenzothienyl, dibenzofuranyl or dibenzoselenophenyl.
Preferably, the compound A is any one or a combination of at least two of the following compounds;
Figure BDA0001910670960000051
Figure BDA0001910670960000061
Figure BDA0001910670960000071
Figure BDA0001910670960000081
Figure BDA0001910670960000091
Figure BDA0001910670960000101
Figure BDA0001910670960000111
Figure BDA0001910670960000121
Figure BDA0001910670960000131
Figure BDA0001910670960000141
Figure BDA0001910670960000151
Figure BDA0001910670960000161
Figure BDA0001910670960000171
Figure BDA0001910670960000181
Figure BDA0001910670960000191
Figure BDA0001910670960000201
Figure BDA0001910670960000211
Figure BDA0001910670960000221
Figure BDA0001910670960000231
Figure BDA0001910670960000241
Figure BDA0001910670960000251
Figure BDA0001910670960000261
Figure BDA0001910670960000271
Figure BDA0001910670960000281
Figure BDA0001910670960000291
preferably, the compound B is any one of the following compounds or a combination of at least two of the following compounds;
Figure BDA0001910670960000292
Figure BDA0001910670960000301
Figure BDA0001910670960000311
Figure BDA0001910670960000321
preferably, the compound C is any one of the following compounds or a combination of at least two of the following compounds;
Figure BDA0001910670960000322
Figure BDA0001910670960000331
Figure BDA0001910670960000341
Figure BDA0001910670960000351
preferably, the compound D is any one of the following compounds or a combination of at least two of the following compounds;
Figure BDA0001910670960000361
Figure BDA0001910670960000371
Figure BDA0001910670960000381
Figure BDA0001910670960000391
Figure BDA0001910670960000401
Figure BDA0001910670960000411
Figure BDA0001910670960000421
Figure BDA0001910670960000431
Figure BDA0001910670960000441
Figure BDA0001910670960000451
Figure BDA0001910670960000461
Figure BDA0001910670960000471
Figure BDA0001910670960000481
Figure BDA0001910670960000491
in the present invention, the compound a can be obtained by the following method: firstly, 2, 4-dibromoaniline and phenylboronic acid are subjected to Suuki reaction to obtain an intermediate 2, 4-diphenylaniline, then the intermediate is subjected to reaction with 2-bromo-9, 9-dimethylfluorene to obtain an intermediate A ', and a halide and the intermediate A' are subjected to Buchwald-Hartwig coupling reaction to synthesize a product.
The synthetic route is as follows:
Figure BDA0001910670960000492
in the present invention, the compound B can be obtained by the following method: carbazole and halide are synthesized to obtain an intermediate through a palladium-catalyzed Buchwald-Hartwig coupling reaction, and then the intermediate is continuously coupled with arylamine compounds through Buchwald-Hartwig coupling.
A representative synthetic route is as follows:
Figure BDA0001910670960000501
in the present invention, the compound C can be obtained by the following method: arylamine compounds and halides can be synthesized into an intermediate through palladium-catalyzed Buchwald-Hartwig coupling reaction, and then the intermediate and boric acid compounds are subjected to Suzuki coupling.
A representative synthetic route is as follows:
Figure BDA0001910670960000502
in the present invention, the compound D can be obtained by the following method: firstly, carbazole derivatives and fluorinated aromatic hydrocarbons are subjected to substitution reaction to obtain halides, then bromide and boric acid compounds are subjected to Suzuki coupling to obtain intermediates, and then arylamine compounds and the intermediates are subjected to palladium-catalyzed Buchwald-Hartwig coupling reaction to synthesize products.
A representative synthetic route is as follows:
Figure BDA0001910670960000511
preferably, the thickness of the light extraction layer is 20-1000nm, such as 25nm, 30nm, 35nm, 40nm, 45nm, 48nm, 50nm, 55nm, 60nm, 65nm, 70nm, 75nm, 80nm, 100nm, 200nm, 500nm, 600nm, 700nm, 800nm, 900nm, etc., preferably 45-80 nm.
Preferably, the light extraction layer is prepared at an evaporation rate of
Figure BDA0001910670960000512
Preferably, the glass transition temperatures of compounds A, B, C, and D are both greater than 100 ℃, e.g., 115 ℃, 120 ℃, 130 ℃, 132 ℃, 135 ℃, 139 ℃, 145 ℃, etc., preferably greater than 130 ℃.
In the prior art, the commonly used NPB for the light extraction layer has a refractive index of 1.6 and the structure is as follows:
Figure BDA0001910670960000513
the refractive index of the commonly used transparent electrode is about 1.9, which is not beneficial to the extraction of light, so that the prepared organic electroluminescent device has low luminous efficiency, and photons generated inside cannot be effectively emitted; the compound is selected, the refractive index of the compound is preferably 1.90-1.95, and the refractive index of the compound is larger than that of the transparent electrode, so that light can be taken out conveniently, and the efficiency of the finally obtained organic electroluminescent device can be improved.
The four compounds selected by the invention have higher glass transition temperatures, can ensure that the compounds can form a compact film in an amorphous state after evaporation, contain rigid groups such as fluorene rings, carbazolyl and the like, can realize the mutual crossing of the groups among molecules, avoid the free rotation of the groups, and enable the material to have higher density, thereby having higher refractive index, being well applied to OLED top-emitting devices, being effective in light-emitting devices of various colors and bringing good device efficiency.
The invention provides a structural schematic diagram of the organic electroluminescent device, which is shown in table 1, and an ITO anode 1, a hole injection layer 2, a hole transport layer 3, a blue light emitting layer or a green light emitting layer or a red light emitting layer 4, an electron transport layer 5, a cathode 6 and a light extraction layer 7 are sequentially arranged from bottom to top.
The organic electroluminescent device is prepared by a vacuum evaporation method, can also be prepared by other methods, and is not limited to vacuum deposition. The invention is illustrated only with devices prepared by vacuum deposition.
The preparation method comprises the steps of cleaning a substrate, drying, pretreating, putting the substrate into a cavity, and sequentially carrying out vacuum deposition on a hole injection layer, a hole transport layer, a luminescent layer, an electron transport layer (electron injection layer), a cathode and a light extraction layer.
The substrate is a rigid substrate or a flexible substrate, the rigid substrate comprises a glass substrate, a Si substrate and the like, and the flexible substrate comprises a polyvinyl alcohol (PVA) film, a Polyimide (PD) film, a Polyester (PET) film and the like; the substrate of the present invention is preferably a rigid glass substrate.
The anode may preferably be a conductive compound, alloy, metal or mixture of such materials having a large work function. Inorganic materials may be used, including metals or metal oxides, laminates of metals and metals or metals and non-metals, and the like, the metal oxides including Indium Tin Oxide (ITO), zinc oxide (ZnO), Indium Zinc Oxide (IZO), tin oxide (SnO), and the like, and the metals including gold, silver, copper, aluminum, and the like, which have a high work function; ITO is preferred as the anode of the present invention.
The hole injection layer is formed by doping 6% of F4TCNQ with MATADA, and has the following structure:
Figure BDA0001910670960000521
NPB is selected as the raw material for preparing the hole transport layer.
The light-emitting layer comprises a blue light-emitting layer or a green light-emitting layer or a red light-emitting layer, wherein the host material of the blue light-emitting layer is selected from the following materials:
Figure BDA0001910670960000522
the blue dye is selected from:
Figure BDA0001910670960000523
the green host is selected from:
Figure BDA0001910670960000524
Figure BDA0001910670960000531
the green dye is selected from:
Figure BDA0001910670960000532
the red host is selected from:
Figure BDA0001910670960000533
Figure BDA0001910670960000541
the red dye is selected from:
Figure BDA0001910670960000542
the electron transport layer is prepared by blending two materials, and the main material is selected from the following materials:
Figure BDA0001910670960000543
the doping materials are:
Figure BDA0001910670960000544
the cathode is magnesium silver mixture, metal such as LiF/Al, ITO, etc., metal mixture, oxide, etc., and Yb/magnesium silver mixture is preferred in the invention.
The raw materials for preparing the light extraction layer provided by the invention are preferably compounds-3, B8, C9 and D11, the glass transition temperature of the compounds is more than 130 ℃, and the refractive index of the compounds is more than 1.90.
Compared with the prior art, the invention has the following beneficial effects:
the light extraction layer adopted by the invention utilizes the characteristic of high refractive index, can effectively promote light extraction, improves the efficiency of the device, and obviously improves the light extraction efficiency of the organic electroluminescent device obtained by the invention.
Drawings
Fig. 1 is a schematic structural diagram of an organic electroluminescent device provided by the present invention.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Example 1
An OLED organic electroluminescent device is prepared by the following steps:
on an anode glass substrate having a film thickness of 150nm and formed thereon Indium Tin Oxide (ITO)/Ag/Indium Tin Oxide (ITO), a vacuum deposition method was used to obtain a glass substrate having a vacuum degree of 2 × 10-4And depositing each film layer under Pa. Firstly, forming a MATADA-6% F4TCNQ film on ITO, wherein the evaporation rate ratio of the MATADA to the F4-TCNQ is 1:0.06, the evaporation rate of the MATADA is 1 angstrom/second, and the total thickness is 100 nm; followed by deposition of 10nm of NPB at an evaporation rate of 1 angstrom/sec. Co-evaporating a blue light main body BFH-1 and a dye BFD-1 from different evaporation sources to form a blue light emitting layer, wherein the evaporation rate ratio of the main body to the dye is 1:0.05, the evaporation rate of the main body is 1 angstrom/second, and the thickness of the blue light emitting layer is 25 nm; depositing ET-1: Liq with the thickness of 25nm as an electron transport layer, wherein the proportion is 1:1, and the evaporation rate is 1 angstrom/second; then depositing Yb with the thickness of 1nm as an electron injection layer, wherein the evaporation rate is 0.1 angstrom/second; then, a film of Ag and Mg (11%) was formed, the ratio of the deposition rate of Ag to Mg was 1:0.11, the deposition rate of Ag was 1A/s, the total thickness was 13nm, and the film was used as a transparent cathode, and finally, 55nm of compound-3 was deposited as a light extraction layer.
Example 2:
the only difference from example 1 is that the thickness of compound-3 in this example is 45 nm.
Example 3:
the only difference from example 1 is that the thickness of compound-3 in this example is 60 nm.
Example 4:
the only difference from example 1 is that the thickness of compound-3 in this example is 80 nm.
Example 5:
the only difference from example 1 is that the thickness of compound-3 in this example is 20 nm.
Example 6:
the only difference from example 1 is that the thickness of compound-3 in this example is 100 nm.
Example 7:
the only difference from example 1 is that the thickness of compound-3 in this example is 500 nm.
Example 8:
the only difference from example 1 is that the thickness of compound-3 in this example is 1000 nm.
Example 9:
an OLED organic electroluminescent device is prepared by the following steps:
on an anode glass substrate having a film thickness of 150nm and formed thereon Indium Tin Oxide (ITO)/Ag/Indium Tin Oxide (ITO), a vacuum deposition method was used to obtain a glass substrate having a vacuum degree of 2 × 10-4And depositing each film layer under Pa. Firstly, forming a MATADA-6% F4TCNQ film on ITO, wherein the evaporation rate ratio of the MATADA to the F4-TCNQ is 1:0.06, the evaporation rate of the MATADA is 1 angstrom/second, and the total thickness is 100 nm; then depositing 10nm NPB with the evaporation rate of 1 angstrom/second; co-evaporating a blue light main body BFH-1 and a dye BFD-1 from different evaporation sources to form a blue light emitting layer, wherein the evaporation rate ratio of the main body to the dye is 1:0.05, the evaporation rate of the main body is 1 angstrom/second, and the thickness of the blue light emitting layer is 25 nm; ET-1: Liq with a thickness of 25nm was deposited as an electron transport layer in a ratio of 1:1 and at an evaporation rate of 1 Angstrom/sec. Then depositing Yb with the thickness of 1nm as an electron injection layer, wherein the evaporation rate is 0.1 angstrom/second; then, a film of Ag and Mg (11%) was formed, the ratio of the deposition rate of Ag to that of Mg was 1:0.11, the deposition rate of Ag was 1A/s, the total thickness was 13nm, and the film was used as a transparent cathode, and finally, 55nm of B8 was deposited as a light extraction layer, thereby obtaining an organic electroluminescent device.
Example 10:
an OLED organic electroluminescent device is prepared by the following steps:
on an anode glass substrate having a film thickness of 150nm and formed thereon Indium Tin Oxide (ITO)/Ag/Indium Tin Oxide (ITO), a vacuum deposition method was used to obtain a glass substrate having a vacuum degree of 2 × 10-4For each membrane under PaThe layers are deposited. Firstly, forming a MATADA-6% F4TCNQ film on ITO, wherein the evaporation rate ratio of the MATADA to the F4-TCNQ is 1:0.06, the evaporation rate of the MATADA is 1 angstrom/second, and the total thickness is 100 nm; then depositing 10nm NPB with the evaporation rate of 1 angstrom/second; co-evaporating a blue light main body BFH-1 and a dye BFD-1 from different evaporation sources to form a blue light emitting layer, wherein the evaporation rate ratio of the main body to the dye is 1:0.05, the evaporation rate of the main body is 1 angstrom/second, and the thickness of the blue light emitting layer is 25 nm; depositing ET-1: Liq with the thickness of 25nm as an electron transport layer, wherein the proportion is 1:1, and the evaporation rate is 1 angstrom/second; then depositing Yb with the thickness of 1nm as an electron injection layer, wherein the evaporation rate is 0.1 angstrom/second; then, a film of Ag and Mg (11%) was formed, the ratio of the deposition rate of Ag to that of Mg was 1:0.11, the deposition rate of Ag was 1A/s, the total thickness was 13nm, and the film was used as a transparent cathode, and finally, 55nm of C9 was deposited as a light extraction layer, thereby obtaining an organic electroluminescent device.
Example 11:
an OLED organic electroluminescent device is prepared by the following steps:
on an anode glass substrate having a film thickness of 150nm and formed thereon Indium Tin Oxide (ITO)/Ag/Indium Tin Oxide (ITO), a vacuum deposition method was used to obtain a glass substrate having a vacuum degree of 2 × 10-4And depositing each film layer under Pa. Firstly, forming a MATADA-6% F4TCNQ film on ITO, wherein the evaporation rate ratio of the MATADA to the F4-TCNQ is 1:0.06, the evaporation rate of the MATADA is 1 angstrom/second, and the total thickness is 100 nm; then depositing 10nm NPB with the evaporation rate of 1 angstrom/second; co-evaporating a blue light main body BFH-1 and a dye BFD-1 from different evaporation sources to form a blue light emitting layer, wherein the evaporation rate ratio of the main body to the dye is 1:0.05, the evaporation rate of the main body is 1 angstrom/second, and the thickness of the blue light emitting layer is 25 nm; depositing ET-1: Liq with the thickness of 25nm as an electron transport layer, wherein the proportion is 1:1, and the evaporation rate is 1 angstrom/second; then depositing Yb with the thickness of 1nm as an electron injection layer, wherein the evaporation rate is 0.1 angstrom/second; then, a film of Ag and Mg (11%) was formed, the ratio of the deposition rate of Ag to that of Mg was 1:0.11, the deposition rate of Ag was 1A/s, the total thickness was 13nm, and the film was used as a transparent cathode, and finally, 55nm of D11 was deposited as a light extraction layer, thereby obtaining an organic electroluminescent device.
Example 12:
an OLED organic electroluminescent device is prepared by the following steps:
on an anode glass substrate having a film thickness of 150nm and formed thereon Indium Tin Oxide (ITO)/Ag/Indium Tin Oxide (ITO), a vacuum deposition method was used to obtain a glass substrate having a vacuum degree of 2 × 10-4And depositing each film layer under Pa. Firstly, forming a MATADA-6% F4TCNQ film on ITO, wherein the evaporation rate ratio of the MATADA to the F4-TCNQ is 1:0.06, the evaporation rate of the MATADA is 1 angstrom/second, and the total thickness is 120 nm; followed by 20nm of NPB deposited at an evaporation rate of 1 angstrom/sec. Co-evaporating a green light main body GPH-1 and a dye GPD-1 from different evaporation sources to form a green light emitting layer, wherein the evaporation rate ratio of the main body to the dye is 1:0.05, the evaporation rate of the main body is 1 angstrom/second, and the thickness of the green light emitting layer is 40 nm; depositing ET-1: Liq with the thickness of 25nm as an electron transport layer, wherein the proportion is 1:1, and the evaporation rate is 1 angstrom/second; then depositing Yb with the thickness of 1nm as an electron injection layer, wherein the evaporation rate is 0.1 angstrom/second; then, a film of Ag and Mg (11%) was formed, the ratio of the deposition rate of Ag to Mg was 1:0.11, the deposition rate of Ag was 1A/s, the total thickness was 13nm, and the film was used as a transparent cathode, and finally, a compound-3 of 60nm was deposited as a light extraction layer, thereby obtaining an organic electroluminescent device.
Example 13:
the only difference from example 7 is that the thickness of Compound-3 in this example is 55 nm.
Example 14:
the only difference from example 8 is that the thickness of compound-3 in this example is 65 nm.
Example 15:
an OLED organic electroluminescent device is prepared by the following steps:
on an anode glass substrate having a film thickness of 150nm and formed thereon Indium Tin Oxide (ITO)/Ag/Indium Tin Oxide (ITO), a vacuum deposition method was used to obtain a glass substrate having a vacuum degree of 2 × 10-4And depositing each film layer under Pa. Firstly, forming a MATADA-6% F4TCNQ film on ITO, wherein the evaporation rate ratio of the MATADA to the F4-TCNQ is 1:0.06, the evaporation rate of the MATADA is 1 angstrom/second, and the total thickness is 120 nm; then depositing 20nm NPB with the evaporation rate of 1 angstrom/second; co-evaporation of green bodies GPH-1 and GPH-1 from different evaporation sourcesThe dye GPD-1 is used as a green light emitting layer, the evaporation rate ratio of the main body to the dye is 1:0.05, the evaporation rate of the main body is 1 angstrom/second, and the thickness of the green light emitting layer is 40 nm; depositing ET-1: Liq with the thickness of 25nm as an electron transport layer, wherein the proportion is 1:1, and the evaporation rate is 1 angstrom/second; then depositing Yb with the thickness of 1nm as an electron injection layer, wherein the evaporation rate is 0.1 angstrom/second; then, a film of Ag and Mg (11%) was formed, the ratio of the deposition rate of Ag to that of Mg was 1:0.11, the deposition rate of Ag was 1A/s, the total thickness was 13nm, and the film was used as a transparent cathode, and finally 60nm of B8 was deposited as a light extraction layer, thereby obtaining an organic electroluminescent device.
Example 16:
an OLED organic electroluminescent device is prepared by the following steps:
on an anode glass substrate having a film thickness of 150nm and formed thereon Indium Tin Oxide (ITO)/Ag/Indium Tin Oxide (ITO), a vacuum deposition method was used to obtain a glass substrate having a vacuum degree of 2 × 10-4And depositing each film layer under Pa. Firstly, forming a MATADA-6% F4TCNQ film on ITO, wherein the evaporation rate ratio of the MATADA to the F4-TCNQ is 1:0.06, the evaporation rate of the MATADA is 1 angstrom/second, and the total thickness is 120 nm; then depositing 20nm NPB with the evaporation rate of 1 angstrom/second; co-evaporating a green light main body GPH-1 and a dye GPD-1 from different evaporation sources to form a green light emitting layer, wherein the evaporation rate ratio of the main body to the dye is 1:0.05, the evaporation rate of the main body is 1 angstrom/second, and the thickness of the green light emitting layer is 40 nm; depositing ET-1: Liq with the thickness of 25nm as an electron transport layer, wherein the proportion is 1:1, and the evaporation rate is 1 angstrom/second; then depositing Yb with the thickness of 1nm as an electron injection layer, wherein the evaporation rate is 0.1 angstrom/second; then, a film of Ag and Mg (11%) was formed, the ratio of the deposition rate of Ag to Mg was 1:0.11, the deposition rate of Ag was 1A/s, the total thickness was 13nm, and the film was used as a transparent cathode, and finally, 60nm of C9 was deposited as a light extraction layer, thereby obtaining an organic electroluminescent device.
Example 17:
an OLED organic electroluminescent device is prepared by the following steps:
on an anode glass substrate having a film thickness of 150nm and formed thereon Indium Tin Oxide (ITO)/Ag/Indium Tin Oxide (ITO), a vacuum deposition method was used to obtain a glass substrate having a vacuum degree of 2 × 10-4Each film layer is aligned under PaAnd (6) carrying out deposition. Firstly, forming a MATADA-6% F4TCNQ film on ITO, wherein the evaporation rate ratio of the MATADA to the F4-TCNQ is 1:0.06, the evaporation rate of the MATADA is 1 angstrom/second, and the total thickness is 120 nm; then depositing 20nm NPB with the evaporation rate of 1 angstrom/second; co-evaporating a green light main body GPH-1 and a dye GPD-1 from different evaporation sources to form a green light emitting layer, wherein the evaporation rate ratio of the main body to the dye is 1:0.05, the evaporation rate of the main body is 1 angstrom/second, and the thickness of the green light emitting layer is 40 nm; depositing ET-1: Liq with the thickness of 25nm as an electron transport layer, wherein the proportion is 1:1, and the evaporation rate is 1 angstrom/second; then depositing Yb with the thickness of 1nm as an electron injection layer, wherein the evaporation rate is 0.1 angstrom/second; then, a film of Ag and Mg (11%) was formed, the ratio of the deposition rate of Ag to that of Mg was 1:0.11, the deposition rate of Ag was 1A/s, the total thickness was 13nm, and the film was used as a transparent cathode, and finally, D11 of 60nm was deposited as a light extraction layer, thereby obtaining an organic electroluminescent device.
Example 18:
an OLED organic electroluminescent device is prepared by the following steps:
on an anode glass substrate having a film thickness of 150nm and formed thereon Indium Tin Oxide (ITO)/Ag/Indium Tin Oxide (ITO), a vacuum deposition method was used to obtain a glass substrate having a vacuum degree of 2 × 10-4And depositing each film layer under Pa. Firstly, forming a MATADA-6% F4TCNQ film on ITO, wherein the evaporation rate ratio of the MATADA to the F4-TCNQ is 1:0.06, the evaporation rate of the MATADA is 1 angstrom/second, and the total thickness is 140 nm; then depositing 20nm NPB with the evaporation rate of 1 angstrom/second; co-evaporating a red light main body RH-1 and a dye RPD-1 from different evaporation sources to form a red light emitting layer, wherein the evaporation rate ratio of the main body to the dye is 1:0.05, the evaporation rate of the main body is 1 angstrom/second, and the thickness of the red light emitting layer is 35 nm; depositing ET-1: Liq with the thickness of 25nm as an electron transport layer, wherein the proportion is 1:1, and the evaporation rate is 1 angstrom/second; then depositing Yb with the thickness of 1nm as an electron injection layer, wherein the evaporation rate is 0.1 angstrom/second; then, a film of Ag and Mg (11%) was formed, the ratio of the deposition rate of Ag to Mg was 1:0.11, the deposition rate of Ag was 1A/s, the total thickness was 13nm, and the film was used as a transparent cathode, and finally, a compound-3 of 60nm was deposited as a light extraction layer, thereby obtaining an organic electroluminescent device.
Example 19:
the only difference from example 13 is that the thickness of Compound-3 in this example is 55 nm.
Example 20:
the only difference from example 14 is that the thickness of Compound-3 in this example is 65 nm.
Example 21:
an OLED organic electroluminescent device is prepared by the following steps:
on an anode glass substrate having a film thickness of 150nm and formed thereon Indium Tin Oxide (ITO)/Ag/Indium Tin Oxide (ITO), a vacuum deposition method was used to obtain a glass substrate having a vacuum degree of 2 × 10-4And depositing each film layer under Pa. Firstly, forming a MATADA-6% F4TCNQ film on ITO, wherein the evaporation rate ratio of the MATADA to the F4-TCNQ is 1:0.06, the evaporation rate of the MATADA is 1 angstrom/second, and the total thickness is 140 nm; then depositing 20nm NPB with the evaporation rate of 1 angstrom/second; co-evaporating a red light main body RH-1 and a dye RPD-1 from different evaporation sources to form a red light emitting layer, wherein the evaporation rate ratio of the main body to the dye is 1:0.05, the evaporation rate of the main body is 1 angstrom/second, and the thickness of the red light emitting layer is 35 nm; depositing ET-1: Liq with the thickness of 25nm as an electron transport layer, wherein the proportion is 1:1, and the evaporation rate is 1 angstrom/second; then depositing Yb with the thickness of 1nm as an electron injection layer, wherein the evaporation rate is 0.1 angstrom/second; then, a film of Ag and Mg (11%) was formed, the ratio of the deposition rate of Ag to that of Mg was 1:0.11, the deposition rate of Ag was 1A/s, the total thickness was 13nm, and the film was used as a transparent cathode, and finally 60nm of B8 was deposited as a light extraction layer, thereby obtaining an organic electroluminescent device.
Example 22:
an OLED organic electroluminescent device is prepared by the following steps:
on an anode glass substrate having a film thickness of 150nm and formed thereon Indium Tin Oxide (ITO)/Ag/Indium Tin Oxide (ITO), a vacuum deposition method was used to obtain a glass substrate having a vacuum degree of 2 × 10-4And depositing each film layer under Pa. Firstly, forming a MATADA-6% F4TCNQ film on ITO, wherein the evaporation rate ratio of the MATADA to the F4-TCNQ is 1:0.06, the evaporation rate of the MATADA is 1 angstrom/second, and the total thickness is 140 nm; then depositing 20nm NPB with the evaporation rate of 1 angstrom/second; co-evaporation of red-light main body RH-1 from different evaporation sources and dyeThe material RPD-1 is used as a red light emitting layer, the evaporation rate ratio of the main body to the dye is 1:0.05, the evaporation rate of the main body is 1 angstrom/second, and the thickness of the red light emitting layer is 35 nm; depositing ET-1: Liq with the thickness of 25nm as an electron transport layer, wherein the proportion is 1:1, and the evaporation rate is 1 angstrom/second; then depositing Yb with the thickness of 1nm as an electron injection layer, wherein the evaporation rate is 0.1 angstrom/second; then, a film of Ag and Mg (11%) was formed, the ratio of the deposition rate of Ag to Mg was 1:0.11, the deposition rate of Ag was 1A/s, the total thickness was 13nm, and the film was used as a transparent cathode, and finally, 60nm of C9 was deposited as a light extraction layer, thereby obtaining an organic electroluminescent device.
Example 23:
an OLED organic electroluminescent device is prepared by the following steps:
on an anode glass substrate having a film thickness of 150nm and formed thereon Indium Tin Oxide (ITO)/Ag/Indium Tin Oxide (ITO), a vacuum deposition method was used to obtain a glass substrate having a vacuum degree of 2 × 10-4And depositing each film layer under Pa. Firstly, forming a MATADA-6% F4TCNQ film on ITO, wherein the evaporation rate ratio of the MATADA to the F4-TCNQ is 1:0.06, the evaporation rate of the MATADA is 1 angstrom/second, and the total thickness is 140 nm; then depositing 20nm NPB with the evaporation rate of 1 angstrom/second; co-evaporating a red light main body RH-1 and a dye RPD-1 from different evaporation sources to form a red light emitting layer, wherein the evaporation rate ratio of the main body to the dye is 1:0.05, the evaporation rate of the main body is 1 angstrom/second, and the thickness of the red light emitting layer is 35 nm; ET-1: Liq with a thickness of 25nm was deposited as an electron transport layer in a ratio of 1:1 and at an evaporation rate of 1 Angstrom/sec. Then depositing Yb with the thickness of 1nm as an electron injection layer, wherein the evaporation rate is 0.1 angstrom/second; then, a film of Ag and Mg (11%) was formed, the ratio of the deposition rate of Ag to that of Mg was 1:0.11, the deposition rate of Ag was 1A/s, the total thickness was 13nm, and the film was used as a transparent cathode, and finally, D11 of 60nm was deposited as a light extraction layer, thereby obtaining an organic electroluminescent device.
Example 24:
the only difference from example 1 is that in this example, compound-3 to compound-4 were deposited in a 55nm thickness as light extraction layers in a ratio of 1: 1.
Example 25:
the only difference from example 1 is that in this example, a 55nm thick compound-3: C9 was evaporated as a light extraction layer at a ratio of 1: 1.
Comparative example 1
The only difference from example 1 is that in this comparative example, the raw material for preparing the light extraction layer was NPB.
Comparative example 2
The only difference from example 7 is that in this comparative example, the starting material for the preparation of the light extraction layer was NPB.
Comparative example 3
The only difference from example 13 is that in this comparative example, the starting material for the preparation of the light extraction layer was NPB.
Comparative example 4
The only difference from example 1 is that in this comparative example, the thickness of the light extraction layer compound-3 evaporated was 15 nm.
Comparative example 5
The only difference from example 1 is that in this comparative example, the thickness of the light extraction layer compound-3 evaporated was 1100 nm.
Performance testing
The organic electroluminescent devices provided in examples 1 to 25 and comparative examples 1 to 5 were subjected to performance tests as follows:
the luminance, the voltage and the external quantum efficiency are tested by linking an OSM software with a spectrometer, the voltage is increased from 2V to 6V, the step length is 0.01V, the voltage is applied to two ends of the organic electroluminescent device, the initial voltage is set, and a series of curves of the luminance and the external quantum efficiency along with the voltage change are tested by gradually increasing the external voltage.
The test results are shown in Table 1:
TABLE 1
Figure BDA0001910670960000591
Figure BDA0001910670960000601
It can be seen from the comparison between the examples and the comparative examples 1 to 3 that, compared with the conventional NPB as the raw material of the light extraction layer, the light extraction layer provided by the present invention has significantly improved light extraction efficiency for blue light, green light and red light. As can be seen from the comparison of example 1 and comparative examples 4 to 5, in the present invention, it is preferable that the thickness of the light extraction layer is 45 to 80nm, in which case the resulting electroluminescent device has better light-emitting efficiency.
The applicant states that the present invention is illustrated by the above examples of the organic electroluminescent device of the present invention, but the present invention is not limited to the above process steps, i.e. it does not mean that the present invention must rely on the above process steps to be carried out. It will be apparent to those skilled in the art that any modification of the present invention, equivalent substitutions of selected materials and additions of auxiliary components, selection of specific modes and the like, which are within the scope and disclosure of the present invention, are contemplated by the present invention.

Claims (11)

1. An organic electroluminescent device comprising a first electrode layer, a light-emitting layer, a second electrode layer, and a light extraction layer provided outside the second electrode layer, wherein the light extraction layer comprises any one of compounds A, B, C or D or a combination of at least two of compounds;
wherein A has a structure shown in formula I:
Figure FDA0001910670950000011
wherein L independently represents one of a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C3-C30 heteroarylene; ra、RbThe same or different, each is independently selected from C1-C20 alkyl, C1-C20 alkenyl or C1-C20 alkynyl, RaAnd RbAre not connected with each other or are connected to form a ring structure; r is selected from one of C1-C20 alkyl, C1-C20 alkenyl, C1-C20 alkynyl, C1-C20 alkoxy, C6-C30 aryl and C3-C30 heteroaryl, and p is an integer of 0-7; ar is selected from heteroaryl represented by the formula A, or substituted or unsubstituted aryl or heteroaryl of C6-C30 which is different from the formula A, and the substituted groups are respectively and independently selected from halogen, C1-C12 alkyl, C1-C12 alkoxy, C6-C12 aryl, C3-C12 heteroaryl, cyano or hydroxy;
Figure FDA0001910670950000012
in the formula A, L1Independently represent one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group; "" denotes the attachment site to the parent nucleus; r1Selected from C1-C20 alkyl, C1-C20 alkenyl, C1-C20 alkynyl, C1-C20 alkoxy, C6-C30 aryl, C3-C30 heteroaryl, multiple R1Identical or different, two R in adjacent position1Are not connected with each other or are connected to form a ring; q is an integer from 0 to 7, preferably 0 or 1; x is selected from O, S, NR2Or SiR3R4；R2One selected from the group consisting of C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; r3、R4Each independently selected from one of C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; the substituted groups are respectively and independently selected from halogen, C1-C12 alkyl, C1-C12 alkoxy, C6-C12 aryl, C3-C12 heteroaryl, cyano or hydroxyl, R3And R4Are not connected with each other or are connected with each other to form a ring;
the B has the structure as shown in the formula II;
Figure FDA0001910670950000021
wherein R is5Selected from the group consisting of substituted or unsubstituted aryl or fused ring aryl of C6-C30, substituted or unsubstituted heterocyclic aryl or fused ring heteroaryl of C3-C30; r6And R7Each independently selected from hydrogen, C1-C12 alkyl, C1-C8 alkoxy, C6-C30 substituted or unsubstituted aryl or fused ring aryl, C3-C30 substituted or unsubstituted heterocyclic aryl or fused ring heteroaryl; m and n are each independently selected from integers of 1 to 6; l isaSelected from single bondsOr selected from C1-C12 alkyl, C1-C8 alkoxy, C5-C30 substituted or unsubstituted arylene, C3-C30 substituted or unsubstituted heterocyclic arylene; ar (Ar)1And Ar2Each independently selected from substituted or unsubstituted C6-C30 aryl or fused ring aryl; ar (Ar)3And Ar4Each independently selected from substituted or unsubstituted C6-C30 aryl or fused ring aryl, substituted or unsubstituted C3-C30 heterocyclic aryl or fused ring heteroaryl; the substituted groups are respectively and independently selected from halogen, alkyl or cycloalkyl of C1-C10, alkenyl, alkoxy or thioalkoxy groups of C1-C6, monocyclic aromatic hydrocarbon or fused ring aromatic hydrocarbon groups of C6-C30, monocyclic heteroaromatic hydrocarbon or fused ring heteroaromatic hydrocarbon groups of C3-C30;
c has the structure as shown in formula III;
Figure FDA0001910670950000031
wherein R is8And R9Each independently selected from C1-C12 alkyl, C1-C8 alkoxy, C6-C30 substituted or unsubstituted aryl or fused ring aryl, C3-C30 substituted or unsubstituted heterocyclic aryl or fused ring heteroaryl, and R8And R9Are not connected with each other or are fused with each other to form a ring; r10And R11Each independently selected from H, C1-C12 alkyl, C1-C8 alkoxy, C6-C30 substituted or unsubstituted aryl or fused ring aryl, C3-C30 substituted or unsubstituted heterocyclic aryl or fused ring heteroaryl, or R10And R11In adjacent positions, R10And R11Fused to form a ring; r12Selected from H, substituted or unsubstituted aryl or fused ring aryl of C6-C30, substituted or unsubstituted heterocyclic aryl or fused ring heteroaryl of C3-C30; l isbSelected from single bond, or selected from C1-C12 alkyl, C1-C8 alkoxy, C3-C30 substituted or unsubstituted arylene or fused ring arylene, C3-C30 substituted or unsubstituted heterocyclylene aryl or fused ring heteroarylene; ar (Ar)5And Ar6Each independently selected from substituted or unsubstituted C6-C30 aryl or fused ring aryl, and substituted or unsubstituted C3-C30 heteroA cyclic aryl or fused ring heteroaryl; the substituted groups are respectively and independently selected from halogen, alkyl or cycloalkyl of C1-C10, alkenyl, alkoxy or thioalkoxy groups of C1-C6, monocyclic aromatic hydrocarbon or fused ring aromatic hydrocarbon groups of C6-C30, monocyclic aromatic hydrocarbon or fused ring aromatic hydrocarbon groups containing a heteroatom selected from N, O, S, Si and C6-C30;
d has the structure as shown in formula IV;
Figure FDA0001910670950000041
wherein Ar is7、Ar8Each independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heterocyclic aryl; r13Selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl; k is an integer of 1 to 5; r14、R15Each independently selected from H, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C8 alkoxy, substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heterocyclic aryl, i and j are each independently an integer from 1 to 4, and the substituted groups are each independently selected from halogen, C1-C10 alkyl or cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy or thioalkoxy groups, C6-C30 aryl or C3-C30 heterocyclic aryl;
i and j are each independently greater than 1, R14Two R's, which are identical or different, which are adjacent14Do not form a ring therebetween or form a ring by fusion, R15Two R's, which are identical or different, which are adjacent15Form no ring or form a ring by fusion.
2. The organic electroluminescent device according to claim 1, wherein in the a compound, Ar is selected from a heteroaryl group represented by general formula a, or a condensed aryl group or a condensed heteroaryl group having a large conjugated structure of C6-C30;
in the formula A, L1Represents a single bond or a substituted or unsubstituted C6-C12 arylene group, R1Selected from aryl of C6-C30, heteroaryl of C3-C30, q is 0 or 1, X is selected from NR2O or S; r2Is a substituted or unsubstituted C6-C30 aryl group;
the condensed aryl or condensed heteroaryl with a large conjugated structure of C6-C30 is selected from substituted or unsubstituted naphthyl, phenanthryl, benzophenanthryl, fluoranthenyl, anthracyl, pyrene, dihydropyrene, anise, perylene, fluoranthene, benzanthracene, triphenylene, tetracene, pentacene, benzopyrene, benzofuran, isobenzofuran, benzothiophene, isobenzothiophene, quinoline, isoquinoline, acridine, phenanthridine, benzopyrazole, pyridopyridine, benzo-5, 6-quinoline, benzo-6, 7-quinoline, benzo-7, 8-quinoline, phenothiazine, phenazine, indazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalimidazole, benzoxazole, naphthoxazole, anthraxazole, phenanthroizole, benzopyrazine, benzopyrimidine, quinoxaline, phenanthroline, phenanthroimidazole, benzopyrene, phenanthroiyl, etc, A group of phenazine, naphthyridine, azacarbazole, benzocarbazine, phenanthroline, benzotriazole, purine, pteridine, indolizine, benzothiadiazole, or a combination of these groups;
preferably, the general formula (A) is a group represented by the following general formula (A1),
Figure FDA0001910670950000051
wherein X is selected from N-Ph, O, S, R1Independently selected from aryl groups of C6-C12, r is 0 or 1, t is 0 or 1, and r and t are not simultaneously 1, Ph represents phenyl;
L1represents a single bond or a substituted or unsubstituted phenylene group.
3. The organic electroluminescent device as claimed in claim 1, wherein in the compound B, Ar is1And Ar2Each is independently selected from phenyl or naphthyl;
Ar3and Ar4Each independently selected from phenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, 1-naphthyl, 2-naphthyl1-anthryl, 2-anthryl, 9-anthryl, phenanthryl, indenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9 '-dialkylfluorene, 9' -spirobifluorene, indenofluorene, fluoranthenyl, triphenylene, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, perylenyl, perylene, fluorenyl,
Figure FDA0001910670950000061
a group, 1-tetracenyl, 2-tetracenyl, 9-tetracenyl, dibenzothiapyrrolyl, dibenzothienyl, dibenzofuranyl, dibenzoselenophenyl, carbazolyl or phenylcarbazolyl;
R5selected from the group consisting of phenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, phenanthryl, indenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9 '-dialkylfluorene, 9' -spirobifluorene, indenofluorene, fluoranthenyl, triphenylene, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, perylenyl,
Figure FDA0001910670950000062
A group, 1-tetracenyl, 2-tetracenyl, 9-tetracenyl, dibenzothiapyrrolyl, dibenzothienyl, dibenzofuranyl, dibenzoselenophenyl, carbazolyl or phenylcarbazolyl;
Laselected from phenylene and naphthylene.
4. The organic electroluminescent device according to claim 1, wherein in compound C, Lb is selected from the group consisting of a single bond, phenyl, naphthyl, biphenyl, terphenyl, pyridyl, bipyridyl, pyrimidinyl, pyrrolyl, phenylpyridyl, pyrazinyl, quinolyl, triazinyl, benzotriazinyl, benzopyrazinyl, benzoquinolyl, dibenzopyrrolyl, carbazolyl, 9-phenylcarbazolyl, 9-naphthylcarbazolocarbazolyl or dibenzocarbazolyl;
Ar5and Ar6Each independently selected from phenyl and benzeneAmino, 2-biphenyl, 3-biphenyl, 4-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, phenanthryl, indenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9 '-dialkylfluorene, 9' -spirobifluorene, indenofluorene, fluoranthenyl, triphenylene, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, Perylene group,
Figure FDA0001910670950000071
A phenyl group, a 1-tetracenyl group, a 2-tetracenyl group, a 9-tetracenyl group, a dibenzothiapyrrolyl group, a dibenzothienyl group, a dibenzofuranyl group or a dibenzoselenophenyl group;
R8and R9Each independently selected from methyl, phenyl, biphenyl, naphthyl or fluorenyl, or R8And R9Condensed to form a fluorene ring;
R10and R11Each independently selected from H, methyl, ethyl, phenyl, biphenyl, naphthyl, fluorenyl, spirofluorenyl, pyridyl, bipyridyl, pyrimidinyl, pyrrolyl, phenylpyridyl, pyrazinyl, quinolinyl, triazinyl, benzotriazolyl, benzopyrazinyl, benzoquinolinyl, dibenzopyrrolyl, carbazolyl, 9-phenylcarbazolyl, 9-naphthylcarbazolocarbazolyl or dibenzocarbazolyl, or R10And R11Fused to form an aryl group;
R12selected from the group consisting of H, phenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, phenanthryl, indenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9 '-dialkylfluorene, 9' -spirobifluorene, indenofluorene, fluoranthenyl, triphenylene, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, perylenyl,
Figure FDA0001910670950000072
A group, 1-tetracenyl, 2-tetracenyl, 9-tetracenyl, dibenzothiapyrrolyl, dibenzothienyl, dibenzofuranyl or dibenzoselenophenyl.
5. The organic electroluminescent device as claimed in claim 1, wherein in the compound D, R is13Selected from methyl, ethyl, propyl, cyclohexyl, phenyl, biphenyl, tolyl, 5-methyltetralin, naphthyl, benzofluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, terphenyl, anthracenyl, phenanthrenyl, pyrenyl or pyrenyl
Figure FDA0001910670950000082
A group;
R14、R15each independently selected from H, methyl, ethyl, phenyl, biphenyl, naphthyl, fluorenyl, spirofluorenyl, pyridyl, bipyridyl, pyrimidinyl, pyrrolyl, phenylpyridyl, pyrazinyl, quinolinyl, triazinyl, benzotriazolyl, benzopyrazinyl, benzoquinolinyl, dibenzopyrrolyl, carbazolyl, 9-phenylcarbazolyl, 9-naphthylcarbazolocarbazolyl, or dibenzocarbazolyl;
Ar7、Ar8each independently selected from the group consisting of phenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, phenanthryl, indenyl, benzofluorenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9 '-dialkylfluorene, 9' -spirobifluorenyl, indenofluorenyl, fluorenyl, triphenylene, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, perylenyl,
Figure FDA0001910670950000083
A group, 1-tetracenyl, 2-tetracenyl, 9-tetracenyl, dibenzothiapyrrolyl, dibenzothienyl, dibenzofuranyl or dibenzoselenophenyl.
6. The organic electroluminescent device according to claim 1 or 2, wherein the compound a is any one of the following compounds or a combination of at least two of the following compounds;
Figure FDA0001910670950000081
Figure FDA0001910670950000091
Figure FDA0001910670950000101
Figure FDA0001910670950000111
Figure FDA0001910670950000121
Figure FDA0001910670950000131
Figure FDA0001910670950000141
Figure FDA0001910670950000151
Figure FDA0001910670950000161
Figure FDA0001910670950000171
Figure FDA0001910670950000181
Figure FDA0001910670950000191
Figure FDA0001910670950000201
Figure FDA0001910670950000211
Figure FDA0001910670950000221
Figure FDA0001910670950000231
Figure FDA0001910670950000241
Figure FDA0001910670950000251
Figure FDA0001910670950000261
Figure FDA0001910670950000271
Figure FDA0001910670950000281
Figure FDA0001910670950000291
Figure FDA0001910670950000301
Figure FDA0001910670950000311
Figure FDA0001910670950000321
7. the organic electroluminescent device according to claim 1 or 3, wherein the compound B is any one of the following compounds or a combination of at least two of the following compounds;
Figure FDA0001910670950000322
Figure FDA0001910670950000331
Figure FDA0001910670950000341
Figure FDA0001910670950000351
8. the organic electroluminescent device according to claim 1 or 4, wherein the compound C is any one of the following compounds or a combination of at least two of the following compounds;
Figure FDA0001910670950000352
Figure FDA0001910670950000361
Figure FDA0001910670950000371
Figure FDA0001910670950000381
9. the organic electroluminescent device according to claim 1 or 5, wherein the compound D is any one of the following compounds or a combination of at least two of the following compounds;
Figure FDA0001910670950000391
Figure FDA0001910670950000401
Figure FDA0001910670950000411
Figure FDA0001910670950000421
Figure FDA0001910670950000431
Figure FDA0001910670950000441
Figure FDA0001910670950000451
Figure FDA0001910670950000461
Figure FDA0001910670950000471
Figure FDA0001910670950000481
Figure FDA0001910670950000491
Figure FDA0001910670950000501
Figure FDA0001910670950000511
Figure FDA0001910670950000521
10. the organic electroluminescent device according to claim 1, characterized in that the thickness of the light extraction layer is 20-1000nm, preferably 45-80 nm;
preferably, the light extraction layer is prepared at an evaporation rate of
Figure FDA0001910670950000522
11. The organic electroluminescent device according to claim 1, wherein the glass transition temperatures of compounds A, B, C and D are both greater than 100 ℃, preferably greater than 130 ℃.
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