CN109860425B - Organic electroluminescent device containing covering layer and application - Google Patents
Organic electroluminescent device containing covering layer and application Download PDFInfo
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Abstract
The present invention relates to an organic electroluminescent device having a capping layer, the organic electroluminescent device comprising: a substrate layer; a first electrode over the substrate; an organic light emitting functional layer over the first electrode; a second electrode over the organic light emitting functional layer; and a capping layer over the second electrode, wherein the capping layer comprises an organic compound having a different type of heteroarylamine structure with a high glass transition temperature and molecular thermal stability; the absorption in the visible light field is low, the refractive index is high, and the light extraction efficiency of the OLED device can be effectively improved after the light extraction film is applied to a CPL layer of the OLED device; the invention also relates to the use of the organic electroluminescent arrangement according to the invention comprising a cover layer for a display or illumination device.
Description
Technical Field
The present invention relates to an organic electroluminescent device, and more particularly, to an organic electroluminescent device having a capping layer (capping layer) that is effective in improving light extraction efficiency.
Background
The Organic Light Emission Diodes (OLED) device technology can be used for manufacturing novel display products and novel lighting products, is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has wide application prospect. The OLED device has a sandwich-like structure and comprises electrode layers and organic light-emitting functional layers sandwiched between different electrode layers, and various different electrode layers, organic light-emitting functional layers and other related material layers are mutually overlapped together according to the application to form the OLED device. The OLED device is a current-driven type device, and when a voltage is applied to both end electrodes thereof to act on positive and negative charges in the organic functional material layer by an electric field, the positive and negative charges are further recombined in the organic light emitting functional layer, i.e., OLED electroluminescence is generated.
Currently, the OLED display technology has been applied in the fields of smart phones, tablet computers, and the like, and will be further expanded to the large-size application fields of televisions and the like. Since there is a great gap between the external quantum efficiency and the internal quantum efficiency of the OLED, the development of the OLED is greatly restricted. Therefore, how to improve the light extraction efficiency of the OLED becomes a hot point of research. Total reflection occurs at the interface between the ITO thin film and the glass substrate and the interface between the glass substrate and the air, the light emitted to the space outside the OLED device accounts for about 20% of the total amount of the organic material thin film EL, and the remaining about 80% of the light is confined mainly in the organic material thin film, the ITO thin film, and the glass substrate in the form of guided waves. It can be seen that the light extraction efficiency of conventional OLED devices is low (about 20%), which severely restricts the development and application of OLEDs. Therefore, it is of great interest to reduce the total reflection effect in OLED devices and to increase the ratio of light coupled into the external space in front of the device (light extraction efficiency).
Currently, an important method for improving the light extraction efficiency of an OLED is to form structures such as folds, photonic crystals, microlens arrays (MLAs), and the addition of surface coatings on the light extraction surface. The first two methods structurally affect the angular distribution of the radiation spectrum of the OLED, and the third method has a complex preparation process. The surface covering layer is simple in process, the luminous efficiency is improved by more than 30%, and people pay attention to the technology.
Therefore, in order to overcome the current situation that the light extraction efficiency of the OLED device is low, it is desirable to use a cover layer (light extraction material layer) that can achieve higher light extraction efficiency in the device structure, and to reduce the angle dependence of the device.
Disclosure of Invention
In view of the above problems of the prior art, the inventors of the present invention have found that, when a capping layer is prepared using a specific type of organic compound and an organic electroluminescent device is prepared using the capping layer, the organic electroluminescent device prepared from the capping layer prepared using the organic compound has an improved current efficiency, an improved light extraction efficiency, and a reduced angle dependence, because the specific type of organic compound has a high refractive index in the visible light region and a low extinction coefficient. Therefore, the present application uses an organic compound that can be used for a capping layer, which can be stably film-formed in a certain manner for the preparation of an organic electroluminescent device, and the light extraction efficiency of the prepared OLED device is effectively improved while the angle dependence of light emission is alleviated.
An object of the present invention is to provide an organic electroluminescent device comprising:
a substrate layer;
a first electrode over the substrate;
an organic light emitting functional layer over the first electrode;
a second electrode over the organic light emitting functional layer; and
a cover layer over the second electrode;
wherein the covering layer comprises an organic compound based on a heteroaryl amine structure, and the structure of the organic compound is shown as a general formula (1):
L1、L2、L3independently represent a single bond, a substituted or unsubstituted 6-to 60-membered arylene group, a substituted or unsubstituted 5-to 60-membered heteroarylene group containing one or more hetero atoms; l1, L2And L3May be the same or different;
in the general formula (1), R1Is represented by a structure shown in a general formula (2) or a general formula (3); r2、R3Each independently represents a structure represented by general formula (2), general formula (3), general formula (4) or general formula (5);
in the general formula (2), the general formula (3) and the general formula (4), X1、X2、X3Independently represent-O-, -S-, -C (R)10)(R11)-、-N(R12)-；
General formula (2), general formula (3),In the general formula (4) and the general formula (5), R4～R19Each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a halogen, a cyano group, or C1-10Alkyl of (C)1-10An alkoxy group of (a), a substituted or unsubstituted 6-to 60-membered aryl group, a substituted or unsubstituted 5-to 60-membered heteroaryl group containing one or more heteroatoms; r4、R7、R8、R9And each independently represents a structure represented by the general formula (6);
general formula (6) by CM1-CM2Key, CM2-CM3Key, CM3-CM4A bond is attached to formula (2);
general formula (6) by CM5-CM6Key, CM6-CM7Key, CM7-CM8A bond is attached to formula (4);
general formula (6) by CM9-CM10Key, CM10-CM11Key, CM11-CM12Key, CM13-CM14Key, CM14-CM15Key, CM15-CM16A bond is attached to formula (5);
the R is10～R12Are each independently represented by C1-10Alkyl of (C)1-10One of an alkoxy group of (a), a substituted or unsubstituted 6-to 60-membered aryl group, and a substituted or unsubstituted 5-to 60-membered heteroaryl group containing one or more heteroatoms;
the substituent of the substituted 6-60-membered aryl or the substituted 5-60-membered heteroaryl is selected from protium atom, deuterium atom, tritium atom, halogen atom, cyano group, C1-20Alkyl of (C)1-10One or more of alkoxy, 6-20 membered aryl, 5-20 membered heteroaryl containing one or more heteroatoms;
the heteroatom in the heteroaryl group is selected from nitrogen, oxygen or sulfur.
Further preferably, L is1、L2、L3Each independently represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted furylene group, a substituted or unsubstituted pyrimidylene group, one of a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyridazinylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted quinolylene group, a substituted or unsubstituted isoquinolylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted cinnolinylene group, a substituted or unsubstituted naphthyridinylene group;
the R is10、R11Each independently represents methyl, phenyl, biphenyl; r12Represented by one of phenyl, naphthyl, biphenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, quinoxalinyl, cinnolinyl, quinazolinyl and naphthyridinyl;
the R is4～R9Each independently represents one of a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a halogen, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a quinolyl group, an isoquinolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzimidazolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a naphthyridinyl group, a dibenzofuranyl group, and an N-phenyl;
the substituent is selected from protium atom, deuterium atom, tritium atom, halogen atom, cyano group, C1-20Alkyl of (C)1-10One or more of alkoxy, 6-20 membered aryl, 5-20 membered heteroaryl containing one or more heteroatoms;
the heteroatom in the heteroaryl group is selected from nitrogen, oxygen or sulfur.
Preferably, the specific compound having the structure represented by the general formula (1) is any one of the following structures:
the material n (450nm) > 2.2, k (450nm) < 0.05 and n (620nm) > 1.9 of the covering layer; n is the refractive index of the material and k is the extinction coefficient of the material.
The second electrode is a magnesium-silver mixed electrode.
The mass ratio of magnesium to silver in the second electrode is 5: 95-95: 5; the thickness of the magnesium silver electrode is 5 nm-20 nm.
The organic light-emitting functional layer comprises a combination of at least 2 of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer.
The hole injection layer at least contains one of a compound A, a compound B or a compound C; the electron transport layer or the electron injection layer contains a compound D; the material adjacent to and between the second electrode is Yb.
A lighting or display device comprising said organic electroluminescent device; and a LiF layer is arranged on the covering layer to be used as a protective layer.
The organic light-emitting functional layer and the covering layer material are formed in a vapor deposition, spin coating, ink-jet printing or screen printing mode.
The beneficial technical effects of the invention are as follows:
1. compared with the traditional organic electroluminescent device taking Alq3 as a covering layer, the organic electroluminescent device containing the heteroaryl amine structure has higher light-emitting efficiency, better viewing deflection and better inhibition on the angle dependence of the wavelength of the emitted light;
2. compared with the traditional organic electroluminescent device taking Alq3 as a covering layer, the organic electroluminescent device containing the heteroaryl amine structure performs TFE packaging under the CVD condition, the device is good, and the black spot phenomenon cannot be generated;
3. compared with the traditional organic electroluminescent device taking Alq3 as a covering layer, the organic electroluminescent device containing the heteroaryl amine structure has high yield, and because the intermolecular interaction force of the heteroaryl amine structure compound of the covering layer is low, the evaporation temperature of the material in a vacuum state is generally lower than 340 ℃, so that the evaporation material is not decomposed in a long time in mass production, and the deformation influence of heat radiation of the evaporation temperature on the evaporation MASK (MASK plate) is reduced; the organic electroluminescent device has good application effect and industrialization prospect.
4. The organic electroluminescent devices prepared according to the invention, which contain the covering layer according to the invention prepared from the heteroarylamine structure, can be used in the field of OLED lighting and displays, in particular in the commercial field, for example in the display screens of products and devices such as POS machines and ATM machines, copiers, vending machines, gaming machines, kiosks, gas stations, card punches, access control systems, electronic scales, etc.; the field of communication, for example, display screens of products such as 3G mobile phones, various video intercom systems (videophones), mobile network terminals, ebooks (electronic books), and the like; the computer field, such as display screens of home and business computers (PC/workstation, etc.), PDAs and notebook computers; consumer electronics products, such as decorative items (soft screens) and lamps, various audio devices, MP3, calculators, digital cameras, head-mounted displays, digital video cameras, portable DVDs, portable televisions, electronic clocks, handheld game consoles, various household appliances (OLED televisions), and the like; in the traffic field, various kinds of indication display screens such as GPS, car audio, car phone, airplane instrument, and equipment are used. Such as a microdisplay, which was originally used by fighter pilots, and now wearable computers are used, mobile devices are not limited by the large size and high power consumption of the displays. Preferably, the organic electroluminescent device prepared according to the invention, which contains the inventive coating layer prepared from the inventive compound, can be used in the fields of illumination and display, preferably in the fields of smart phones, tablet computers and the like, smart wearable devices, large-size application fields such as televisions, VR, micro-display fields, and automobile center control screens or automobile tail lamps. The embodiment of the present invention is not particularly limited in this regard.
Drawings
FIG. 1 is a schematic cross-sectional view of an organic electroluminescent device according to the present invention;
wherein 100 is a substrate layer, 200 is a first electrode layer, 300 is an organic light emitting functional layer, 400 is a second electrode layer, and 500 is a cover layer.
FIG. 2 is a schematic cross-sectional view of an organic light-emitting functional layer in an organic electroluminescent device according to the present invention;
here, 310(HIL) is a hole injection layer, 320(HTL) is a hole transport layer, 330(EBL) is an electron blocking layer, 340(EML) is an emission layer, 350(HBL) is a hole blocking layer, 360(ETL) is an electron transport layer, and 370(EIL) is an electron injection layer.
Fig. 3 is a configuration of the light emitting layer 340: formed by longitudinally overlapping composite luminescent layer materials;
wherein one of EM1 and EM2 is blue organic luminescent layer material, and the other is green, yellow or red luminescent layer material.
Fig. 4 is a configuration of the light emitting layer 340: formed by longitudinally overlapping composite luminescent layer materials;
one of EM1, EM2 and EM3 is blue organic luminescent layer material, and the other two of the EM1, EM2 and EM3 are green, yellow or red luminescent layer material.
Fig. 5 is a configuration of the light emitting layer 340: formed by composite luminescent layer materials which are arranged together in a transverse direction;
wherein EM1, EM2 and EM3 are respectively a blue organic luminescent layer material, a green organic luminescent layer material and a red organic luminescent layer material, and are not sequentially arranged.
FIG. 6 is a two-layer device structure of the light-emitting layer 340: carrying out charge transport through the connecting layer;
fig. 7 is a three-layer device structure of the light-emitting layer 340: carrying out charge transport through the connecting layer;
FIG. 8 is a photograph showing an accelerated crystallization experiment of a film of Alq3 vapor-deposited film;
FIG. 9 is a photograph showing an experiment of accelerated crystallization of a vapor-deposited film of Material 1;
FIG. 10 is a photograph of Alq3 and a LiF vapor deposited film blackened after a CVD process;
FIG. 11 is a photograph of compound 1 and a LiF vapor deposited film of the present invention after a CVD process.
Detailed Description
Mixing 56 compounds with Alq3The compound was measured (tested in an atmospheric environment) for refractive index n and extinction coefficient k using an ellipsometer (U.S. J.A.Woollam Co. model: ALPHA-SE); the highest occupied molecular orbital HOMO energy level is tested by photoelectron spectroscopy (IPS-3) under an atmospheric environment, Eg is actually tested by an ultraviolet spectrum, and LUMO is HOMO + Eg; glass transition temperature Tg measured by differential scanning calorimetryMeasured by a method (DSC, DSC204F1 differential scanning calorimeter of German Nachi company), and the temperature rise rate is 10 ℃/min; the data are shown in table 1 below:
TABLE 1
As can be seen from the data in table 1, compared with the currently used materials such as Alq3, the organic compound based on the heteroarylamine structure contained in the organic electroluminescent device of the present invention has a higher Tg, and the lower the Tg, the more unstable the material is in the device, and the easier the material is crystallized, thereby resulting in a decrease in light extraction efficiency and a decrease in viewing deflection angle, as shown in fig. 8 and 9, fig. 8 is a photograph of a film accelerated crystallization experiment of an Alq3 deposited film, and fig. 9 is a photograph of a film accelerated crystallization experiment of a material 1 deposited film, and there is no crystallization; meanwhile, the organic compound based on the heteroaryl amine structure in the organic electroluminescent device of the present invention has a LUMO level shallower than-3 ev, and in the application process of the OLED panel, LiF is evaporated after CPL film thickness, and then TFE encapsulation is performed under CVD condition, the deeper the LUMO level, the easier the CPL material reacts with LiF under CVD energy to form a new substance, so that the color of the entire capping layer material is blackened, which affects the light extraction efficiency of the device, as shown in fig. 10 and 11, fig. 10 is a photograph of blackening after CVD process of Alq3 and LiF evaporated film, and fig. 11 is a photograph of after CVD process of the compound 1 and LiF evaporated film of the present invention, and the material is unchanged.
The present invention also provides a structure and a manufacturing method of an organic electroluminescent device having a capping layer, and the present invention will be further described in detail with reference to the accompanying drawings and examples. However, they may be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
As shown in fig. 1, the substrate layer 100 may be any substrate used in a typical organic light-emitting device. It may be a glass or transparent plastic substrate, a substrate of an opaque material such as silicon or stainless steel, or a flexible PI film. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, water resistance, and different directions of use depending on the properties of the substrates.
The first electrode layer 200 is formed on the substrate layer 100, and the first electrode layer 200 may be a cathode or an anode. Here, the first electrode layer 200 may be a reflective electrode such as a reflective film formed of silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb), or an alloy thereof; and a transparent or semitransparent electrode layer having a high work function and formed on the reflective film.
The transparent or semitransparent electrode layer may be formed of Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), zinc oxide (ZnO), Aluminum Zinc Oxide (AZO), Indium Gallium Oxide (IGO), indium oxide (In)2O3) Or tin oxide (SnO)2) And (4) forming.
The first electrode layer 200 can be formed by a method such as sputtering, ion plating, vacuum evaporation, spin coating, electron beam evaporation, or Chemical Vapor Deposition (CVD), and is preferably formed by sputtering.
The thickness of the first electrode layer 200 depends on the material used, and is generally in the range of 5nm to 1 μm, preferably 10nm to 1 μm, more preferably 10nm to 500nm, particularly preferably 10nm to 300nm, and most preferably 10nm to 200 nm.
As shown in fig. 2, the organic light emitting function layer 300 may include an emission layer 340(EML), and a hole transport region may be formed between the EML and the first electrode layer 200, and an electron transport region may be formed between the EML and the second electrode layer 400. The hole transport region may include at least one of a hole injection layer 310(HIL), a hole transport layer 320(HTL), and an electron blocking layer 330 (EBL). The electron transport region may include at least one of a hole blocking layer 350(HBL), an electron transport layer 360(ETL), and an electron injection layer 370 (EIL). Accordingly, the organic light emitting function layer 300 includes at least 2 combinations of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
The thickness of the organic light emitting functional layer 300 is 50nm to 1000 nm.
As the material for the hole injection layer, the hole transport layer, and the electron blocking layer (HIL310, HTL320, and EBL330), any material may be selected from known materials for OLED devices.
Examples of the above-mentioned materials may be phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridoline derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quinone derivatives, styrylanthracene derivatives, styrylamine derivatives and other styrene compounds, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyarylalkane derivatives, polyphenylenes and their derivatives, polythiophenes and their derivatives, poly-N-vinylcarbazole derivatives, thiophene oligomers and other conductive polymer oligomers, aromatic tertiary amine compounds, styrene amine compounds, triamines, tetraamines, benzidine, propynediamine derivatives, hydrazone derivatives, stilbene derivatives, phenanthroline derivatives, phenanthr, P-phenylenediamine derivatives, m-phenylenediamine derivatives, 1 '-bis (4-diarylaminophenyl) cyclohexane, 4,4' -bis (diarylamine) biphenyls, bis [4- (diarylamino) phenyl ] methanes, 4,4 '-bis (diarylamino) terphenyls, 4,4' -bis (diarylamino) quaterphenyls, 4,4 '-bis (diarylamino) diphenyl ethers, 4,4' -bis (diarylamino) diphenylsulfanes, bis [4- (diarylamino) phenyl ] dimethylmethanes, bis [4- (diarylamino) phenyl ] -bis (trifluoromethyl) methanes, or 2, 2-diphenylethylene compounds, and the like.
At least one of the HIL310 and the HTL320 may further include a charge generation material for improving conductivity. The charge generating material may be a p-dopant. Non-limiting compounds of P-dopants are for example: quinone derivatives such as Tetracyanoquinodimethane (TCNQ) and 2,3,5, 6-tetrafluoro-tetracyano-1, 4-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives, such as 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN); or a cyclopropane derivative, such as 4,4',4 "- ((1E,1' E, 1" E) -cyclopropane-1, 2, 3-trimethylenetri (cyanoformylidene)) tris (2,3,5, 6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.
The triplet state (T1) energy level of the required material in EBL330 is higher than the T1 energy level of the host material in the light-emitting layer 340, and can act as a barrier to energy loss of the light-emitting layer material; the HOMO energy level of the EBL330 material is between the HOMO energy level of the HTL320 material and the HOMO energy level of the main body material of the light-emitting layer 340, so that holes can be injected into the light-emitting layer from the positive electrode, and meanwhile, the EBL330 material is required to have high hole mobility, so that hole transmission is facilitated, and the application power of the device is reduced; the LUMO level of the EBL330 material is higher than that of the host material of the light emitting layer 340, and functions as an electron blocking, that is, the EBL330 material is required to have a wide forbidden bandwidth (Eg). The EBL330 material satisfying the above conditions may be triarylamine derivatives, fluorene derivatives, spirofluorene derivatives, dibenzofuran derivatives, carbazole derivatives, and the like. Among them, triarylamine derivatives such as N4, N4-bis ([1,1 '-biphenyl ] -4-yl) -N4' -phenyl N4'- [1, 1': 4', 1 "-terphenyl ] -4-yl- [1,1' -biphenyl ] -4,4' -diamine; spirofluorene derivatives, such as N- ([1,1 '-diphenyl ] -4-yl) -N- (9, 9-dimethyl-9H-furan-2-yl) -9,9' -spirobifluoren-2-amine; dibenzofuran derivatives such as N, N-bis ([1,1' -biphenyl ] -4-yl) -3' - (dibenzo [ b, d ] furan-4-yl) - [1,1' -biphenyl ] -4-amine, but not limited thereto.
In order to obtain a high efficiency OLED device, the light emitting layer 340 may use the same doping material, or use multiple doping materials, the doping material may be a pure fluorescent material, a delayed fluorescence (TADF) material, or a phosphorescent material, or may be a combination of different fluorescent materials, TADF materials, and phosphorescence, and the light emitting layer 340 may be a single light emitting layer material, or may be a composite light emitting layer material stacked together in a transverse or longitudinal direction. The light-emitting layer 340 constituting the above-described OLED light-emitting body is exemplified by the following various configurations:
(1) a single organic light emitting layer material;
(2) any combination of blue organic light emitting layer material and green, yellow or red light emitting layer material, not in sequential order, as shown in fig. 3;
(3) any two combinations of the blue organic light-emitting layer material and the green, yellow or red light-emitting layer material are not arranged in the front-back order, as shown in fig. 4;
(4) the blue organic light emitting layer material, the green organic light emitting layer material and the red organic light emitting layer material are transversely arranged as shown in fig. 5;
(5) any combination of blue organic light emitting layer material and green, yellow or red light emitting layer material, and carrying out charge transport through the connecting layer to form a two-layer device structure, as shown in fig. 6;
(6) any two of the blue organic light emitting layer material and the green, yellow or red light emitting layer material are combined and charge transport is performed through the connection layer to form a three-stack device structure, as shown in fig. 7.
Preferably, the organic light emitting function layer includes a light emitting layer including 1 or a combination of at least 2 of blue light emitting pixels, green light emitting pixels, red light emitting pixels, and yellow light emitting pixels.
In order to adjust the effective combination of carrier charges in the light-emitting layer, the film thickness of the light-emitting layer 340 constituting the OLED light-emitting body may be arbitrarily adjusted as necessary, or light-emitting layers that are not colored may be alternately stacked and combined as necessary, or charge blocking layers for different functional purposes may be added to organic layers adjacent to the light-emitting layer.
The host material constituting the light-emitting layer of the above-mentioned OLED light-emitting device needs to have not only bipolar charge transport characteristics but also an appropriate energy level to efficiently transfer excitation energy generated by recombination of electrons and holes to a guest light-emitting material, i.e., a dopant material. Examples of such a material include a distyrylarylene derivative, a stilbene derivative, a carbazole derivative, a triarylamine derivative, an anthracene derivative, a pyrene derivative, a triazine derivative, a xanthone derivative, a triphenylene derivative, an azabenzene derivative, a coronene derivative, bis (2-methyl-8-quinoline) (p-phenylphenol) aluminum (BAlq), and the like.
As a guest material capable of generating blue fluorescence, blue phosphorescence, green fluorescence, green phosphorescence, and blue-green fluorescence, there is no particular limitation, and such a material is required to have not only extremely high fluorescence quantum emission efficiency but also an appropriate energy level to efficiently absorb excitation energy of a host material to emit light. Examples thereof include stilbene amine derivatives, pyrene derivatives, anthracene derivatives, triazine derivatives, xanthone derivatives, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, chrysene derivatives, phenanthroline derivatives, distyrylbenzene derivatives, and tetraphenylbutadiene derivatives. Among them, 4' -bis [2- (9-ethylcarbazol-2-yl) -vinyl ] biphenyl (BCzVBi), perylene, and the like can be used, and there can be mentioned one or a combination of two or more kinds of compounds alone, such as a tetrakisbenzene-based compound, a bisphenyl-based compound, a benzimidazole-based compound, a benzoxazole-based compound, a benzooxadiazole-based compound, a styrylbenzene compound, a distyrylpyrazine-based compound, a butadiene-based compound, a naphthalimide compound, a perillene-based compound, an aldazine-based compound, a cyclopentadiene-based compound, a pyrrolopyrrole-formyl-based compound, a styrylamine-based compound, a coumarine-based compound, an aromatic xylylline-based compound, a metal complex compound having an 8-quinolate-based substance as a ligand, or a polyphenyl-based compound. Among these compound materials, the present invention can be exemplified by specific examples of aromatic xylylline-based compounds such as: 4,4 '-bis (2, 2-di-1-butylphenyl vinyl) diphenyl (abbreviated as DTBPBBi) or 4,4' -bis (2, 2-diphenylvinyl) diphenyl (abbreviated as DPVBi), and the like and derivatives thereof.
The content (doping amount) of the fluorescent guest material with respect to the fluorescent host material is preferably 0.01 wt% or more and 20 wt% or less, and more preferably 0.1 wt% or more and 10 wt% or less. When a blue fluorescent guest material is used as the fluorescent guest material, the content thereof is preferably 0.1 wt% or more and 20 wt% or less with respect to the fluorescent host material. Within this range, an effective energy distribution between the high-energy blue emitter and the low-energy red emitter can be balanced, and desired electroluminescence with a balanced intensity of blue and red emissions can be obtained.
The light-emitting layer 340 included in the OLED device may be made of not only the fluorescent light-emitting material but also a phosphorescent material. Compared with fluorescent materials, the phosphorescent materials can simultaneously utilize singlet excitons and triplet excitons in the light emitting process, and theoretically, the internal quantum efficiency can reach 100 percent, so that the light emitting efficiency of the light emitting device can be greatly improved.
The blue phosphorescent dopant material is not particularly limited as long as it has a blue phosphorescent light-emitting function. Examples thereof include metal complexes of iridium, titanium, platinum, rhenium, palladium, and the like. Among these, complexes in which at least one of the ligands of the metal complex has a phenylpyridine skeleton, a bipyridine skeleton, a porphyrin skeleton, or the like are preferable. More specifically, bis [4, 6-difluorophenylpyridinium-N, C2 '] -picolinium iridium, tris [2- (2, 4-difluorophenyl) pyridium-N, C2' ] iridium, bis [2- (3, 5-trifluoromethyl) pyridium-N, C2 '] -picolinium iridium or bis [4, 6-difluorophenylpyridinium-N, C2' ] iridium acetylacetonate may be mentioned.
The green phosphorescent dopant is not particularly limited as long as it has a green phosphorescent light-emitting function. Examples of the phosphorescent dopant include metal complexes of iridium, ruthenium, platinum, rhenium, palladium, etc., complexes having a phenylpyridine skeleton, a bipyridine skeleton, a porphyrin skeleton, etc., at least one of the ligands of the metal complexes, and more specifically, iridium (Ir (ppy) of the surface formula (face) -tris (2-phenylpyridine)3) Bis [ 2-phenylpyridine-N, C2']Iridium acetylacetonate or tris [ 5-fluoro-2- (5-trifluoromethyl-2-pyridine) phenyl-C, N]Iridium, and the like.
Examples of the red phosphorescent dopant include platinum (II) octaethylporphyrin (PtOEP), tris (2-phenylisoquinoline) iridium (Ir (piq)3) Bis (2- (2 '-benzothienyl) -pyridine-N, C3') iridium (acetylacetonate) (Btp)2Ir (acac)), etc.
The content (doping amount) of the phosphorescent dopant material is preferably 0.01 wt% or more and 30 wt% or less, and more preferably 0.1 wt% or more and 20 wt% or less, with respect to the phosphorescent host material. When the green phosphorescent dopant material is used, it is preferably 0.1 wt% or more and 20 wt% or less with respect to the phosphorescent host material.
The phosphorescent host material is not particularly limited as long as the triplet energy is larger than that of the phosphorescent dopant. Examples thereof include carbazole derivatives, phenanthroline derivatives, triazine derivatives, triazole derivatives, and quinolinol-like metal complexes. Specific examples thereof include 4,4',4 ″ -tris (9-carbazolyl) triphenylamine, 4' -bis (9-carbazolyl) -2,2 '-dimethylbiphenyl, 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 3-phenyl-4- (1' -naphthyl) -5-phenylcarbazole, and tris (8-hydroxyquinoline) aluminum (Alq)3) Or bis- (2-methyl-8-hydroxyquinoline-4- (phenylphenol) aluminum, and the like.
Besides the fluorescent or phosphorescent host-guest materials used in the light-emitting layer, the light-emitting layer materials can also adopt non-host-guest doped system materials, such as exciplex energy transfer, interface light emission and the like; the light-emitting layer material can also adopt a host-guest material with a Thermal Activation Delayed Fluorescence (TADF) function, and a mode that the TADF function material and the fluorescence and phosphorescence materials are mutually combined and matched.
The materials constituting the hole blocking layer 350 and the electron transport layer 360 of the OLED device may be any materials selected from materials for OLEDs having electron transport properties. Examples of such a material include oxadiazole derivatives such as 1, 3-bis [5 ' - (p-tert-butylphenyl) -1,3, 4-oxadiazol-2 ' -yl ] benzene, 2- (4-biphenyl) -5- (4-tert-butylphenyl) -1,3, 4-oxadiazole, triazole derivatives such as 3- (4 ' -tert-butylphenyl) -4-phenyl-5- (4 "-biphenyl) -1,2, 4-triazole, triazine derivatives, quinoline derivatives, quinoxaline derivatives, diphenoquinone derivatives, nitro-substituted ketene derivatives, thiopyran dioxide derivatives, anthraquinone dimethane derivatives, thiopyran dioxide derivatives, heterocyclic tetraanhydrides such as naphthyl perylene, carbodiimide, fluorene derivatives, anthraquinone dimethane derivatives, perylene derivatives, and the like, Anthrone derivatives, distyrylpyrazine derivatives, silacyclopentadiene derivatives, phenanthroline derivatives, imidazopyridine derivatives, or the like.
Further, there may be mentioned organometallic complexes such as bis (10-benzo [ h ] quinolinolato) beryllium, beryllium salts of 5-hydroxybrass, aluminum salts of 5-hydroxybrass, and the like, or metal complexes of 8-hydroxyquinoline or derivatives thereof, such as tris (8-quinolinolato) aluminum (Alq), tris (5, 7-dichloro-8-quinolinolato) aluminum, bis (2-methyl-8-quinolinolato) (p-phenylphenolate) aluminum (BAlq), and tris (5, 7-dibromo-8-quinolinolato) aluminum. And metal chelator compounds containing a chelator, such as a quinolinol metal complex, such as a plant hormone (generally, 8-quinolinol) such as tris (2-methyl-8-quinolinol) aluminum. Examples of metal complexes in which the central metal of these metal complexes is replaced with beryllium, indium, magnesium, copper, calcium, tin, zinc, or aluminum are also given. It is preferable to use a nonmetal, a metal phthalocyanine or a substance having an alkyl group, a sulfo group or the like substituted at the terminal thereof. Among them, 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 3-phenyl-4- (1' -naphthalene) -5-phenyl-1, 2, 4-Triazole (TAZ) are more preferably used.
The triplet state (T1) energy level of the required material in HBL350 is higher than the T1 energy level of the host material in the light-emitting layer 340, and can act as a barrier to energy loss of the light-emitting layer material; the HUMO energy level of the EBL350 material is lower than that of the main body material of the light-emitting layer 340, so that the hole blocking effect is achieved, and meanwhile, the HBL350 material is required to have high electron mobility, so that electron transmission is facilitated, and the application power of the device is reduced; the HBL350 material satisfying the above conditions may be a triazine derivative, an azabenzene derivative, or the like. Among them, triazine derivatives are preferable; but is not limited thereto.
The EIL370 may be formed from one or more of the following: an alkali metal; an alkaline earth metal; halides of alkali metals and alkaline earth metals; oxides of alkali metals and alkaline earth metals, carbonates of alkali metals and alkaline earth metals; alkali metal and alkaline earth metal oxalates or alkali metal and alkaline earth metal fluoroaluminates. Examples thereof include Li, Ca, Sr, LiF, CsF, BaO and Li2CO3、CaCO3、Li2C2O4、Cs2C2O4、CsAlF4. In some embodiments, the EIL370 can include at least one metal, such as Yb, Sc. One or more of V, Y, In, Ce, Sm, Eu or Tb.
The second electrode layer 400 is formed on the organic light emitting function layer 300, and may be a cathode, an anode, a transparent electrode, or a semi-transparent electrode. The second electrode layer 400 may be made of lithium, calcium, lithium fluoride/aluminum, silver, magnesium, or an alloy thereof into a thin film having a low work function. Further, the second electrode layer 400 may be made of an alloy including silver and at least one metal including aluminum, platinum, ytterbium, chromium, or magnesium. Also, the weight ratio of Ag in the alloy may be the same as the other metal ratio or greater or less than the weight of the other metal. For example: the second electrode layer 400 may be formed of an Ag — Mg alloy, wherein a mass ratio of Ag and Mg may be 90:10 to 10: 90. Alternatively, the second electrode layer 400 may be formed of an alloy including at least one metal such as silver, gold, platinum, copper, nickel, or tungsten and at least one metal such as ytterbium, indium, magnesium, or chromium. These metal films can form transparent or translucent electrodes by adjusting the thickness of the film. Accordingly, light generated from the organic light emitting functional layer 300 may be emitted through the second electrode layer 400. Also, the second electrode layer 400 may have a thickness of 5 to 20 nm.
The capping layer 500 is formed on the second electrode layer 400, and the material used for the capping layer 500 is 1 or a combination of at least 2 of the structures based on heteroarylamines as described in the present invention.
The thickness of the covering layer is 10-1000nm, preferably 50-140 nm.
Referring to fig. 1, the organic electroluminescent device of the present invention includes a substrate layer 100, a first electrode layer 200, an organic light emitting functional layer 300, a second electrode layer 400, and a cover layer 500.
A barrier layer (which may be composed of an inorganic material or/and an organic material for preventing foreign substances from penetrating the substrate and the device) and a wiring layer (which may include a driving TFT, a capacitor, a wire, and a low temperature polysilicon LTPS) may be formed on the substrate layer using a known method.
In a specific embodiment, the first electrode layer 200 may be a reflective electrode and the second electrode layer 400 is a transparent or semi-transparent electrode. Therefore, light generated from the organic light emitting functional layer 300 may be directly emitted from the second electrode layer 400, or may be reflected by the first electrode layer 200 to be emitted toward the second electrode layer 400. The first electrode layer 200 can be prepared by, for example, an evaporation method or a sputtering method. The second electrode layer 400 may be prepared by, for example, a vacuum evaporation method.
The organic light emitting function layer 300 may include an emission layer 340(EML), and a hole transport region may be formed between the EML and the first electrode layer 200, and an electron transport region may be formed between the EML and the second electrode layer 400. The hole transport region may include at least one of a hole injection layer 310(HIL), a hole transport layer 320(HTL), and an electron blocking layer 330 (EBL). The electron transport region may include at least one of a hole blocking layer 350(HBL), an electron transport layer 360(ETL), and an electron injection layer 370 (EIL).
The organic light emitting functional layer 300 may be composed of a small molecular organic material or a high molecular material, and the organic light emitting functional layer 300 may be prepared by various methods such as a vacuum evaporation method, solution spin coating, screen printing, and an inkjet printing method, for example.
The capping layer 500 may be composed of the organic compound based on the heteroarylamine structure, and the capping layer 500 may be prepared using various methods such as a vacuum evaporation method, solution spin coating, screen printing, and an inkjet printing method.
In addition, a full-color organic electroluminescent device including the structure of fig. 3,4, 5,6 or 7 may be prepared by referring to the structure of the organic electroluminescent device of fig. 1, 2. That is, the organic light emitting device according to the embodiments may be configured in various structures, such as a single color light emitting device, an organic electroluminescence device of multi-color light or white light.
The embodiment of the present invention is not particularly limited in this regard.
The effects of the present embodiment are highlighted below by comparing examples and comparative examples.
Examples
The compounds of the invention used in the examples for the covering layer material are compounds 1, 6, 14, 24, 37, 42, 52, 60, 81, 91, 102, 114, 127, 137, 147, 156, 162, 174, 183, 193, 206, 219, 228, 246, 255, 270, 275, 289, 300, 311, 316, 328, 340, 351, 360, 370, 387, 397, 404, 416, 426, 436, 440 of the compounds listed hereinbefore below.
Apparatus example 1:
an organic electroluminescent device was prepared by the following preparation steps, including:
forming an ITO film (first electrode layer 200) with the thickness of 10nm on a low-temperature polycrystalline silicon (LTPS) substrate (substrate layer 100) in a sputtering mode, etching the ITO film into a required pattern, respectively ultrasonically cleaning the ITO film with deionized water, acetone and ethanol for 15 minutes, and then treating the ITO film in a plasma cleaner for 2 minutes; the ITO electrode layer is an anode, and a hole injection layer material HAT-CN is evaporated on the ITO anode layer in a vacuum evaporation mode, the thickness of the hole injection layer material HAT-CN is 10nm, and the layer is used as a hole injection layer 310; evaporating a hole transport material NPB on the hole injection layer 310 in a vacuum evaporation mode, wherein the thickness of the hole transport material NPB is 110nm, and the hole transport material NPB is a hole transport layer 320 and can also be used as a microcavity adjusting layer; evaporating an electron blocking material TCTA (TCTA) with the thickness of 10nm on the hole transport layer 320 in a vacuum evaporation mode, wherein the layer is an electron blocking layer 330; evaporating a blue light emitting layer 340 on the electron blocking layer 330, wherein CBP is used as a host material, BDAVBi is used as a doping material, the mass ratio of BDAVBi to CBP is 5:95, and the thickness is 20 nm; an electron transport material TPBI is evaporated on the light-emitting layer 340 in a vacuum evaporation mode, the thickness of the TPBI is 35nm, and the organic material layer serves as an electron transport layer 360; vacuum evaporating an electron injection layer compound D with the thickness of 1nm on the electron transport layer 360, wherein the layer is an electron injection layer 370; a cathode Yb/Mg: Ag layer is vacuum-evaporated on the electron injection layer 370, the Yb thickness is 1nm, the mass ratio of Mg to Ag is 1:9, the thickness is 14nm, the layer is a second electrode layer 400, and the layer is a cathode layer; on the second electrode layer 400, the compound 1 of the example material of the present invention was deposited by vacuum evaporation to a thickness of 50nm, and this organic material was used as the capping layer 500.
Apparatus example 2:
the procedure was the same as for device example 1, but the following device configuration was used:
ITO (10nm)/NPB Compound A (97:3 mass ratio, 97 mass% of NPB) (10nm)/NPB (150nm)/TCTA (10nm)/CBP Ir (PPy)3(90:10 mass% CBP) (40nm)// TPBI (35 nm)/Compound D (1nm)/Yb (1nm)/Mg: Ag (10:90 mass% Mg) (14 nm)/Compound 1 of the present invention (50 nm).
Apparatus example 3:
the procedure was the same as for device example 1, but the following device configuration was used:
ITO (10nm)/NPB, Compound C (95:5 mass ratio, 95 mass% NPB) (10nm)/NPB (190nm)/TCTA (10nm)/CBP: Ir (pq)2acac (96:4 mass ratio, 96 mass% CBP) (40nm)/TPBI (35 nm)/Compound D (1nm)/Yb (1nm)/Mg: Ag (10:90 mass ratio, 10 mass% Mg) (14 nm)/Compound 1(50nm) of the present invention.
Device examples 4,7, 10, 13, 16, 19, 22, 25, 28, 31, 34, 37, 40, 43, 46, 49, 52, 55, 58, 61, 64, 67, 70, 73, 76, 79, 82, 85, 88, 91, 94, 97, 100, 103, 106, 109, 112, 115, 118, 121, 124, 127:
the preparation method is the same as that of device example 1, except that: compounds 6, 14, 24, 37, 42, 52, 60, 81, 91, 102, 114, 127, 137, 147, 156, 162, 174, 183, 193, 206, 219, 228, 246, 255, 270, 275, 289, 300, 311, 316, 328, 340, 351, 360, 370, 387, 397, 404, 416, 426, 436, 440 were used as capping layer materials for organic electroluminescent devices.
Device embodiments 5,8, 11, 14, 17, 20, 23, 26, 29, 32, 35, 38, 41, 44, 47, 50, 53, 56, 59, 62, 65, 68, 71, 74, 77, 80, 83, 86, 89, 92, 95, 98, 101, 104, 107, 110, 113, 116, 119, 122, 125, 128:
the preparation method is the same as that of device example 2, except that: compounds 6, 14, 24, 37, 42, 52, 60, 81, 91, 102, 114, 127, 137, 147, 156, 162, 174, 183, 193, 206, 219, 228, 246, 255, 270, 275, 289, 300, 311, 316, 328, 340, 351, 360, 370, 387, 397, 404, 416, 426, 436, 440 were used as capping layer materials for organic electroluminescent devices.
Device examples 6, 9,12, 15, 18, 21, 24, 27, 30, 33, 36, 39, 42, 45, 48, 51, 54, 57, 60, 63, 66, 69, 72, 75, 78, 81, 84, 87, 90, 93, 96, 99, 102, 105, 108, 111, 114, 117, 120, 123, 126, 129:
the preparation method is the same as that of device example 3, except that: compounds 6, 14, 24, 37, 42, 52, 60, 81, 91, 102, 114, 127, 137, 147, 156, 162, 174, 183, 193, 206, 219, 228, 246, 255, 270, 275, 289, 300, 311, 316, 328, 340, 351, 360, 370, 387, 397, 404, 416, 426, 436, 440 were used as capping layer materials for organic electroluminescent devices.
After the preparation of the electroluminescent device was completed according to the above-described steps, the current efficiency and the perceived color difference of the device were measured, and the results are shown in table 2. The molecular structural formula of the related material is shown as follows:
comparative apparatus example 1:
the procedure was the same as for device example 1, but the following device configuration was used:
ITO (10nm)/HAT-CN (10nm)/NPB (110nm)/TCTA (10nm)/CBP BDAVBi (95:5 mass ratio, 95 mass% CBP) (40nm)// TPBI (35 nm)/Compound D (1nm)/Yb (1nm)/Mg Ag (10:90 mass ratio, 10 mass% Mg) (14nm)/Alq3(50nm)。
Comparative apparatus example 2:
the procedure was the same as for device example 1, but the following device configuration was used:
ITO (10nm)/NPB: Compound A (97:3 mass ratio, 97 mass% of NPB)/NPB (150nm)/TCTA (10nm)/CBP: Ir (PPy)3(90:10 mass% of CBP) (20nm)// TPBI (35nm) Compound D (1nm)/Yb (1nm)/Mg: Ag (10:90 mass% of Mg) (14nm)/Alq3(50nm)。
Comparative apparatus example 3:
the preparation method is the same as that of the device example 1, and the device structure is different:
ITO (10nm)/NPB Compound C (95:5 mass ratio, 95 mass% NPB) (10nm)/NPB (190nm)/TCTA (10nm)/CBP Ir (pq)2acac (96:4 mass ratio, 96 mass% CBP) (40nm)/TPBI (35 nm)/Compound D (1nm)/Yb (1nm)/Mg: Ag (10:90 mass ratio, 10 mass% Mg) (14nm)/Alq3(50nm)。
Determination of Current efficiency, CIE, perceptible color Difference
The OLED devices of the above examples and comparative examples were measured for current efficiency, CIEx, CIEy and perceived color difference using IVL (current-voltage-luminance) test system (japan システム, ltd.) and selection software EILV20060707, and the results are shown in table 2 below:
TABLE 2
JNCD, perceived color difference, the smaller the chromaticity variation, meaning the better the angular dependence of the wavelength of the emitted light of the organic electroluminescent device is suppressed.
From the results of table 2 it can be seen that: compared with the comparative example, the current efficiency of the organic electroluminescent device prepared by the covering layer prepared by the compound of the invention in the fields of blue light, green light and red light is obviously improved, thereby correspondingly improving the light extraction efficiency.
Compared with the comparative example, the organic electroluminescent device prepared by the covering layer prepared by the compound has smaller perceivable color difference in the fields of blue light, green light and red light, and thus has smaller angle dependence.
Claims (8)
1. An organic electroluminescent device comprising:
a substrate layer;
a first electrode over the substrate;
an organic light emitting functional layer over the first electrode;
a second electrode over the organic light emitting functional layer; and
a cover layer over the second electrode;
wherein the covering layer comprises an organic compound based on a heteroarylamine structure, and is characterized in that the structure of the organic compound is shown as a general formula (1):
L1、L2、L3each independently represents one of a single bond, phenylene and biphenylene; l is1、L2And L3May be the same or different;
in the general formula (1), R1Represented by a structure represented by the general formula (2); r2、R3Each independently represents a structure represented by general formula (2) or general formula (4);
in the general formula (2) and the general formula (4), X1、X3Each independently represents-O-or-S-;
in the general formula (2) and the general formula (4), R4、R7Each independently representIs a hydrogen atom.
2. The organic electroluminescent device according to claim 1, wherein the specific compound having the structure represented by the general formula (1) is any one of the following structures:
3. the organic electroluminescent device according to claim 1, wherein the cover layer material n (450nm) > 2.2, k (450nm) < 0.05, n (620nm) > 1.9; n is the refractive index of the material and k is the extinction coefficient of the material.
4. The organic electroluminescent device according to claim 1, wherein the second electrode is a magnesium-silver mixed electrode.
5. The organic electroluminescent device according to claim 4, wherein the ratio of magnesium to silver in the second electrode is 5:95 to 95: 5; the thickness of the magnesium silver electrode is 5 nm-20 nm.
6. The organic electroluminescent device according to claim 1, wherein the organic light-emitting functional layer comprises a combination of at least 2 of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
7. The organic electroluminescent device according to claim 6, wherein the hole injection layer contains at least one of compound a or compound B or compound C; the electron transport layer or the electron injection layer contains a compound D; the material adjacent to the second electrode and between the two electrodes is Yb;
8. a lighting or display device comprising the organic electroluminescent device according to any one of claims 1 to 7; and a LiF layer is arranged on the covering layer to be used as a protective layer.
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| CN109860425A (en) | 2019-06-07 |
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