CN108976162A - Coating formation compound and organic luminescent device comprising it - Google Patents

Coating formation compound and organic luminescent device comprising it Download PDF

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Publication number
CN108976162A
CN108976162A CN201810531239.XA CN201810531239A CN108976162A CN 108976162 A CN108976162 A CN 108976162A CN 201810531239 A CN201810531239 A CN 201810531239A CN 108976162 A CN108976162 A CN 108976162A
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substituted
unsubstituted
compound
chemical formula
coating
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咸昊完
安贤哲
姜京敏
金熙宙
金东骏
闵丙哲
文锺勋
韩政佑
李萤振
林东焕
林大喆
权桐热
李成圭
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Dongjin Semichem Co Ltd
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • C07—ORGANIC CHEMISTRY
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/805—Electrodes
    • H10K50/81—Anodes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/84—Passivation; Containers; Encapsulations
    • H10K50/844—Encapsulations
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/85—Arrangements for extracting light from the devices
    • H10K50/858—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract

The present invention relates to coating formation compound and comprising the organic luminescent device of the compound, the coating formation of an example of the invention is suitable for organic luminescent device with compound, external light emission efficiency, chromaticity coordinates and the service life of organic luminescent device can be improved.

Description

Coating formation compound and organic luminescent device comprising it
Technical field
The present invention relates to coating formation compound and include its organic luminescent device.
Background technique
In general, organic luminescent device refers to using organic substance the device for converting electrical energy into luminous energy.Organic hair Optical device, which could generally have, forms anode (anode) on substrate top, sequentially forms hole transporting layer, hair on above-mentioned anode top The structure of photosphere, electron supplying layer and cathode (cathode).
Organic luminescent device injects hole from anode, is injected if applying voltage between above-mentioned anode and cathode Electronics is injected from cathode while hole is moved to luminescent layer via hole transporting layer, institute's injected electrons is via electron transport Layer and be moved to luminescent layer.Be moved to above-mentioned luminescent layer hole and electronics in conjunction with and generate exciton (exciton).It is above-mentioned to swash Son becomes ground state under excited state, generates light.
The efficiency of organic luminescent device is commonly divided into internal light emission efficiency and external light emission efficiency.Internal light emission efficiency with Following content is related, be formed in as hole transporting layer, luminescent layer and electron supplying layer etc. first electrode and second electrode it Between organic matter layer in how to efficiently generate exciton and carry out light conversion.It is said by theory, for internal light emission efficiency, for For fluorescence, about 25%, for phosphorescence, about 100%.
On the other hand, external light emission efficiency expression is generated from the organic matter layer being formed between first and second electrode In general efficiency outside light extraction to organic luminescent device with about 20% level of internal light emission efficiency, is extracted outer Portion.
For improving this external light emission efficiency, the i.e. method of light extraction efficiency, be emitted in order to prevent external light into Row is totally reflected and is damaged, and a variety of organic compounds is used as coating (capping layer), in order to improve organic illuminator The performance of part is continually striving to the organic compound that exploitation has high refractive index and thin film stability that external light emission efficiency can be improved Object.
Existing technical literature
Patent document
(patent document 1) KR published patent 10-2004-0098238
Summary of the invention
There is height while the wide band gap that present invention offer is affected with the RGB wavelength not to organic luminescent device Refractive index, thus can be improved the excitation purity of organic luminescent device and the coating formation compound of external light emission efficiency and Organic luminescent device including the coating containing above-mentioned coating formation compound.
But the problem to be solved in the present invention is not limited to problem described above, invention technician should pass through Contents below are expressly understood that the other problems not described.
First embodiment offer of the invention is indicated by following formula 1, is configured at outside the electrode of organic luminescent device The coating of side, which is formed, uses compound:
Chemical formula 1
In above-mentioned chemical formula 1,
Ar1For substituted or unsubstituted C6~50Arlydene or substituted or unsubstituted C5~50Heteroarylidene,
Ar2For substituted or unsubstituted C6~50Aryl or substituted or unsubstituted C5~50Heteroaryl,
Ar and Ar ' is separately substituted or unsubstituted C6~50Aryl or substituted or unsubstituted C5~50's Heteroaryl, Ar can be connected with Ar ' and form ring, or can not also form ring,
L is Direct Bonding, substituted or unsubstituted C6~30Arlydene or substituted or unsubstituted C5~30Miscellaneous sub- virtue Base,
R1To R4It is separately hydrogen, heavy hydrogen, substituted or unsubstituted C1~30Alkyl, substituted or unsubstituted C1~30 Alkoxy, substituted or unsubstituted C2~30Alkenyl, substituted or unsubstituted C6~50Aryl or substituted or unsubstituted C5~50Heteroaryl,
L, m and o is separately 0 or 1 to 4 integer, and n is 0 or integer of 1 to 3.
Second embodiment of the present invention provides a kind of organic luminescent device, comprising: first and second electrode；Organic matter Layer, on the inside of first and second above-mentioned electrode；And coating, it is configured at least one of first and second above-mentioned electrode On the outside of electrode, and compound is used containing coating formation of the invention.
The coating formation of an example of the invention has not to the RGB wavelength band of organic luminescent device with compound come shadow With high refractive index while loud wide band gap, the excitation purity and outer blaze effect of organic luminescent device thus can be improved Rate.
Also, the coating of an example of the invention, which is formed, uses compound, and molecules align is outstanding, as bulk density increases Add, stable film can be formed.Also, by high Tg and Td, inhibit recrystallizationization, production when being not driven organic luminescent device The influence of raw heat, the pollution caused by can reducing because of external air and moisture inside organic luminescent device, thus can mention The service life of high organic luminescent device.
Detailed description of the invention
Fig. 1 shows the schematic diagrams of the organic luminescent device of an example of the invention.
The explanation of appended drawing reference
100: substrate
200: hole injection layer
300: hole transporting layer
400: luminescent layer
500: electron supplying layer
600: electron injecting layer
1000: anode (first electrode)
2000: cathode (second electrode)
3000: coating
Specific embodiment
Hereinafter, referring to attached drawing, the example and embodiment that the present invention will be described in detail, so that the technical field of the invention is general Logical technical staff can be easy to implement.
But the present invention can by it is a variety of it is different in the form of realize, and be not limited to example and embodiment described herein. Also, the part unrelated with explanation is omitted, in the specification, for similar in the figure in order to clearly state the present invention Part, be labelled with similar appended drawing reference.
In the full text of description of the invention, when a component is located at another component "upper", not only include component with The case where another component is in contact, include thes case where there is other component between the two parts.
In the full text of description of the invention, when one structural element of a part " comprising ", unless there are especially opposite It records, then means to may also include other structures element, rather than exclude other structures element.In the full text of description of the invention The term " about " that uses, " substantial " etc. when prompting intrinsic preparation and substance tolerance in mentioned meaning with its numerical value or Meaning close to its numerical value uses, and is undeservedly utilized with the infringer for preventing against one's conscience and is referred to help to understand the present invention The disclosure of accurate or absolute numerical value.Term "~() step " used in the full text of description of the invention or "~ Step " do not mean that " for~the step of ".
In the full text of description of the invention, " their combination " contained in the performance of Markush (Markush) form this One term means one or more of the group that documented multiple structural elements form in the performance by Markush form Mixing or combination, it is meant that including selected from one or more of the group that is made of above-mentioned multiple structural elements.
In the full text of description of the invention, " A and/or B " this record means " A or B or A and B ".
In the full text of description of the invention, term " aryl " means comprising C5-50Aromatic cyclic hydrocarbon group, for example, benzene Base, benzyl, naphthalene, xenyl, terphenyl, fluorenyl, phenanthryl, triphenyl alkenyl, phenylakenyl,Base, fluorane thenyl, Benzo fluorenyl, benzo triphenyl alkenyl, benzoThe aromatic ring of base, anthryl, stilbenyl, pyrenyl etc., " heteroaryl " As the C comprising at least one miscellaneous element3-50Aromatic ring, such as, it is meant that comprising from pyrrolinyl, pyrazinyl, pyridine Base, indyl, isoindolyl, furyl, benzofuranyl, isobenzofuran-base, dibenzofuran group, aisaa benzothiophenyl, two Aisaa benzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, carbazyl, luxuriant and rich with fragrance cry base, acridinyl, phenanthroline, thienyl and by Pyridine ring, pyridine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring, pyrrolidine ring, dioxanes ring, piperazine Phenazine ring, morpholine ring, piperazine ring, carbazole ring, furan nucleus, thiphene ring, oxazole ring, oxadiazoles ring, benzoxazoles ring, thiazole ring, thiophene The aromatic series that diazonium ring, benzothiazole ring, triazole ring, imidazole ring, benzimidazole ring, pyranoid ring, dibenzofurans ring are formed is miscellaneous Ring group.
In the full text of description of the invention, term " substitutive " may imply that can by selected from by heavy hydrogen, halogen, amino, Itrile group, nitro or C1~C30Alkyl, C2~C30Alkenyl, C1~C30Alkoxy, C3~C20Naphthenic base, C3~C20It is miscellaneous Naphthenic base, C6~C30Aryl and C3~C30The base of one or more of group of heteroaryl composition replace.Also, in the present invention In specification full text, identical appended drawing reference is as long as no specifically mentioned content, so that it may have equivalent.
First embodiment offer of the invention is indicated by following formula 1, is configured at outside the electrode of organic luminescent device The coating of side, which is formed, uses compound:
Chemical formula 1
In above-mentioned chemical formula 1,
Ar1For substituted or unsubstituted C6~50Arlydene or substituted or unsubstituted C5~50Heteroarylidene,
Ar2For substituted or unsubstituted C6~50Aryl or substituted or unsubstituted C5~50Heteroaryl,
Ar and Ar ' is separately substituted or unsubstituted C6~50Aryl or substituted or unsubstituted C5~50's Heteroaryl, Ar can be connected with Ar ' and form ring, or can not also form ring,
L is Direct Bonding, substituted or unsubstituted C6~30Arlydene or substituted or unsubstituted C5~30Miscellaneous sub- virtue Base,
R1To R4It is separately hydrogen, heavy hydrogen, substituted or unsubstituted C1~30Alkyl, substituted or unsubstituted C1~30 Alkoxy, substituted or unsubstituted C2~30Alkenyl, substituted or unsubstituted C6~50Aryl or substituted or unsubstituted C5~50Heteroaryl,
L, m and o is separately 0 or 1 to 4 integer, and n is 0 or integer of 1 to 3.
There is the coating formation compound of the above-mentioned chemical formula 1 of an example of the invention the nitrogen of carbazole to pass through arlydene Linker (Ar1) it is incorporated in the structure of 1 arylamine, above-mentioned arylamine can have two fluorenes of diaryl fluorene or spiral shell as aryl.
In the compound of the present invention, the nitrogen of carbazole is incorporated in 1 arylamine by arlydene linker, thus can maintain not The wider band gap that the wavelength in the region RGB can be absorbed has two fluorenes of diaryl fluorene or spiral shell in the end of arylamine, thus has height Refractive index can increase external quantum efficiency.
Also, the nitrogen of carbazole is incorporated in arylamine by arlydene linker, has diaryl fluorene in the end of arylamine Or two fluorenes of spiral shell, when manufacturing film, molecules align and intermolecular accumulation are protruded, and can form stable film.Also, by diaryl Fluorenes can inhibit the recrystallization of film compared with also having high Tg and Td under low molecule, and thermal stability is outstanding, can be from outside Organic luminescent device is protected in air and moisture.
That is, if the coating of the compound containing an example of the invention is configured at outside the electrode of organic luminescent device External light emission efficiency then can be improved in side.When intervening in the organic matter layer on the inside of first and second electrode of organic luminescent device When the light of generation is extracted to outside organic luminescent device, it can prevent from being emitted to external light and be totally reflected and that is lost shows As.
The coating of an example of the invention, which is formed, uses compound, and because structure feature can have high refractive index, film is stablized Property is outstanding, and when being applicable in the coating for organic luminescent device, external light emission efficiency, the chromaticity coordinates of organic luminescent device can be improved And the service life.
An example according to the present invention, in above-mentioned chemical formula 1, Ar1It can be substituted or unsubstituted phenylene, substitution Or it is unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted sub- triphenyl, substituted or unsubstituted Fluorenylidene, two fluorenylidene of substituted or unsubstituted spiral shell or their combination specifically can be phenylene, naphthylene, sub- biphenyl Base, sub- triphenyl, fluorenylidene, dialkylfluorenylene, diaryl fluorenylidene, two fluorenylidene of spiral shell or their combination.
Also, an example according to the present invention, in above-mentioned chemical formula 1, Ar2Can for substituted or unsubstituted phenyl, It is substituted or unsubstituted naphthalene, substituted or unsubstituted xenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted Phenanthryl, substituted or unsubstituted triphenyl, substituted or unsubstituted fluorenyl, two fluorenyl of substituted or unsubstituted spiral shell or their group It closes.Specifically, phenyl, naphthalene, xenyl, terphenyl, phenanthryl, triphenyl, fluorenyl, dialkyl fluorenyl, diaryl be can be Fluorenyl, two fluorenyl of spiral shell or their combination.
Also, an example according to the present invention, in above-mentioned chemical formula 1, above-mentioned L can be Direct Bonding, phenylene, Asia Naphthalene, biphenylene, sub- triphenyl, fluorenylidene, dialkylfluorenylene, diaryl fluorenylidene, two fluorenylidene of spiral shell or their group It closes, can be Direct Bonding or phenylene specifically.
Also, an example according to the present invention, in above-mentioned chemical formula 1, above-mentioned R1To R4It can separately be hydrogen, benzene Base, xenyl or naphthalene can be specifically hydrogen or phenyl.
In an example of the invention, above-mentioned coating formation can be indicated with compound by following formula 2.
Chemical formula 2
In above-mentioned chemical formula 2,
The integer that p is 1 to 4.
In the compound indicated by above-mentioned chemical formula 2, the nitrogen of carbazole is incorporated in arylamine by 1 or more phenylene. That is, as arlydene linker (Ar1) can have phenylene, biphenylene, sub- triphenyl, tetraphenylene, these above-mentioned sub- benzene The connection structure of base is not particularly limited, and can have the connection structure of straight chain type and branched chain type.As described above, when being used as arlydene When linker imports phenylene, bigger band gap is maintained, there can be high refractive index.
Also, in an example of the invention, above-mentioned coating formation compound can be by following formula 3 or chemical formula 4 indicate.
In above-mentioned chemical formula 3 or chemical formula 4,
R5And R6It is separately hydrogen, heavy hydrogen, substituted or unsubstituted C1~44Alkyl, substituted or unsubstituted C1~44 Alkoxy, substituted or unsubstituted C2~44Alkenyl, substituted or unsubstituted C6~44Aryl or substituted or unsubstituted C5~44Heteroaryl,
The integer that p is 1 to 4.
The compound indicated by above-mentioned chemical formula 3 or chemical formula 4, such as the compound indicated by above-mentioned chemical formula 2, carbazole Nitrogen arylamine is incorporated in by 1 or more phenylene.
Also, in the compound indicated by above-mentioned chemical formula 3, arylamine has diphenylfluorene, is indicated by above-mentioned chemical formula 4 Compound in, arylamine have two fluorenes of spiral shell.As described above, bigger band gap can be maintained when there is two fluorenes of diphenylfluorene or spiral shell, There can be high refractive index.
Also, an example according to the present invention, in above-mentioned chemical formula 2 into chemical formula 4, above-mentioned L can be Direct Bonding, Phenylene, naphthylene, biphenylene, sub- triphenyl, fluorenylidene, dialkylfluorenylene, diaryl fluorenylidene, two fluorenylidene of spiral shell or Their combination can be specifically Direct Bonding or phenylene.
Also, in an example of the invention, above-mentioned coating formation compound can be by following formula 5 or chemical formula 6 indicate.
In above-mentioned chemical formula 5 or chemical formula 6,
R5And R6It is separately hydrogen, heavy hydrogen, substituted or unsubstituted C1~44Alkyl, substituted or unsubstituted C1~44 Alkoxy, substituted or unsubstituted C2~44Alkenyl, substituted or unsubstituted C6~44Aryl or substituted or unsubstituted C5~44Heteroaryl,
The integer that p is 1 to 4, the integer that q is 0 or 1 to 4.
The compound indicated by above-mentioned chemical formula 5 or chemical formula 6, such as the compound indicated by above-mentioned chemical formula 2, carbazole Nitrogen arylamine is incorporated in by 1 or more phenylene.
Also, in the compound indicated by chemical formula 5, the nitrogen of arylamine and the diphenylfluorene Direct Bonding as aryl, Or it can be combined by 1 or more phenylene.Also, in the compound indicated by above-mentioned chemical formula 6, the nitrogen of arylamine with As the two fluorenes Direct Bonding of spiral shell of aryl, or can be combined by 1 or more phenylene.That is, the nitrogen of arylamine can pass through As the diphenylfluorene or two fluorenes of spiral shell of aryl and the phenylene as linker (L), biphenylene, sub- triphenyl, tetraphenylene It is connected.The connection structure of these phenylenes is not particularly limited, and can have the connection structure of straight chain type and branched chain type.Institute as above It states, when being connected by 1 or more phenylene, the conjugation of compound can be minimized, inhibit shining for visible light region, can have Effect improves the excitation purity of organic luminescent device.
Also, an example according to the present invention, in above-mentioned chemical formula 2 or 6, Ar2It can be substituted or unsubstituted benzene Base, substituted or unsubstituted naphthalene, substituted or unsubstituted xenyl, substituted or unsubstituted terphenyl, substitution do not take The phenanthryl in generation, substituted or unsubstituted triphenyl, substituted or unsubstituted fluorenyl, two fluorenyl of substituted or unsubstituted spiral shell or they Combination.Specifically, phenyl, naphthalene, xenyl, terphenyl, phenanthryl, triphenyl, fluorenyl, dialkyl fluorenyl, two be can be Aryl fluorenyl, two fluorenyl of spiral shell or their combination.
Also, an example according to the present invention, in above-mentioned chemical formula 2 to 6, above-mentioned R1To R4Can separately be hydrogen, Phenyl, xenyl or naphthalene can be specifically hydrogen or phenyl.
It, can be by as follows by the coating formation compound that above-mentioned chemical formula 1 to 6 indicates in an example of the invention Reaction equation is synthesized, it is not limited to this, it can also be synthesized by a variety of methods.
Reaction equation
In an example of the invention, disclosed below the 1st can be to by the compound that above-mentioned chemical formula 1 indicates Any one compound in 437, it is likely that not limited to this:
Second embodiment of the present invention, providing configuration includes the chemical combination indicated by any of above-mentioned chemical formula 1 to 6 The organic luminescent device of the coating of object.
An example according to the present invention, organic luminescent device can include: first and second electrode；Organic matter layer, between upper It states on the inside of first and second electrode；And coating, it is configured on the outside of at least one electrode in first and second above-mentioned electrode, And the coating formation compound indicated containing any of chemical formula 1 to 6.Wherein, in first electrode or second electrode Two sides in, will not be with using the side adjacent with the organic matter layer between first electrode and second electrode as inside On the outside of an adjacent conduct of organic matter layer.That is, when the outside of first electrode configures coating, in coating and organic matter layer Between intervene first electrode, second electrode outside configure coating when, second is intervened between coating and organic matter layer Electrode.
As soon as example according to the present invention can on the inside of first electrode and second electrode for above-mentioned organic luminescent device Gas chromatography layer is intervened, coating can be formed on the outside of at least one of first and second electrode.The above-mentioned equal shape of coating At on the outside of the outside of first electrode and second electrode, or it is configured in the outside of first electrode or the outside of second electrode. Above-mentioned coating may include coating formation compound of the invention.
An example according to the present invention, coating can individually include the coating formation chemical combination of an example of the invention Object, or can together include two or more or well known compound.
The organic luminescent device of an example of the invention is between first and second electrode, i.e., in first and second electrode Inside includes 1 layer or more of organic matter layer, can form coating in the outside of first and second above-mentioned electrode.Above-mentioned organic matter layer It usually can be hole transporting layer, luminescent layer and the electron supplying layer for constituting illumination region, it is possible to not limited to this.
Above-mentioned organic luminescent device can between first electrode (anode, anode) and second electrode (cathode, cathode) Including 1 layer or more of hole injection layer (HIL), hole transporting layer (HTL), luminescent layer (EML), electron supplying layer (ETL), electronics The organic matter layer of the composition illumination region such as implanted layer (EIL).
For example, above-mentioned organic luminescent device can be prepared according to structure documented in Fig. 1.Organic luminescent device can To it is lower and on stack gradually 3000/ first electrode of coating (anode, hole injecting electrode 1000)/hole injection layer, 200/ hole 500/ electron injecting layer of transfer layer 300/ luminescent layer, 400/ electron supplying layer 600/ second electrode (cathode, electron injection electrode 2000)/coating 3000.
As described above, the coating formation of an example of the invention with compound there is the nitrogen of carbazole to connect by arlydene Base (Ar1) it is incorporated in the structure of 1 arylamine, above-mentioned arylamine has two fluorenes of diaryl fluorene or spiral shell as aryl, thus not Stable film can be only formed, and there is high refractive index, can also increase external quantum efficiency.
In Fig. 1, the substrate for organic luminescent device is can be used in substrate 100, in particular, can be steady for mechanical strength, heat Qualitative, transparent, surface smoothness, ease of handling and the outstanding transparent glass substrate or flexible plastic base of waterproofness Plate.
Hole injecting electrode 1000 is used as the anode for being injected with the hole of machine luminescent device.In order to which hole can be injected, It, can be by tin indium oxide (ITO), indium zinc oxide (IZO), graphene (graphene) etc using the substance with low work function Transparent material formed.
By vacuum deposition method, spin-coating method, casting, LB (Langmuir-Blodgett) method etc. come in above-mentioned anode electricity Pole overburden hole injection layer substance, thus can form hole injection layer 200.Sky is being formed by above-mentioned vacuum deposition method In the case where the implanted layer of cave, the compound of material of the sedimentary condition because being used as hole injection layer 200, needed for hole injection layer Structure and thermal characteristics etc. and it is different, but usually can 50-500 DEG C depositing temperature, 10-8To 10-3The vacuum degree of torr (support), 0.01 toDeposition velocity,It is suitably selected in 5 μm of layer thickness range.Also, it is infused in hole Enter layer surface, deposited charge can be added as needed, layer occurs.Conventional substance can be used as charge generating layer substance, can lift Example HATCN.
Then, by vacuum deposition method, spin-coating method, casting, LB method etc. come in above-mentioned 200 overburden of hole injection layer Thus hole transporting layer substance can form hole transporting layer 300.Hole transporting layer is being formed by above-mentioned vacuum deposition method In the case of, sedimentary condition is different due to the compound used, but typically it will be preferred to, the formation with hole injection layer almost It is selected in identical condition and range.
Above-mentioned hole transporting layer 300 can be used well known compound and be formed.An example according to the present invention, cavity conveying Layer 300 can be 1 layer or more, can form luminous auxiliary layer on above-mentioned hole transporting layer 300.
By the methods of vacuum deposition method, spin-coating method, casting, LB method, in above-mentioned hole transporting layer 300 or the auxiliary that shines Thus depositing light emitting layer substance on layer can form luminescent layer 400.By above-mentioned vacuum deposition method to form luminescent layer the case where Under, sedimentary condition is different due to the compound used, but typically it will be preferred to, almost the same with the formation of hole injection layer Condition and range in selected.Also, well known compound can be used as main body or dopant by above-mentioned emitting layer material.
Also, in the case where being used together in luminescent layer with phosphorescent dopants, triplet exciton or hole in order to prevent The phenomenon that spreading to electron supplying layer can also be laminated hole by vacuum deposition method or spin-coating method and inhibit material (HBL).At this time may be used The hole inhibiting substances used are not particularly limited, but selection in the well known substance of material can be inhibited any from hole is used as Substance utilizes.For example, oxadiazole derivatives or triazole derivative, phenanthroline derivative or Japanese Unexamined Patent Publication 11- can be enumerated Documented hole inhibits material etc. in 329734 (A1), typically, can be used Balq (bis- (8- hydroxy-2-methylquinolines)- Aluminium biphenyl phenates), phenanthroline (phenanthrolines) class compound (such as BCP (Basso of general purpose display (UDC) company Coupoline)) etc..
It is formed with electron supplying layer 500 on 400 top of luminescent layer as formed above, at this point, above-mentioned electron supplying layer can lead to The methods of vacuum deposition method, spin-coating method, casting are crossed to be formed.Also, the sedimentary condition of above-mentioned electron supplying layer is because using Compound and it is different, but typically it will be preferred to, selected in the condition and range almost the same with the formation of hole injection layer.
Later, electron injecting layer 600 can be formed in above-mentioned 500 overburden electron injecting layer substance of electron supplying layer, At this point, above-mentioned electron supplying layer can form conventional electron injection by the method for vacuum deposition method, spin-coating method, casting etc. Layer substance.
Hole injection layer 200, hole transporting layer 300, luminescent layer 400, the electron supplying layer 500 of above-mentioned organic luminescent device Following substance can be used, it is not limited to this.
The yin for injecting electronics is formed on electron injecting layer 600 by the method for vacuum deposition method or sputtering method etc. Pole 2000.As cathode, various metals can be used.Concrete example has the substance of aluminium, gold, silver etc..
Organic luminescent device of the invention can not only use anode, hole injection layer, hole transporting layer, luminescent layer, electricity Sub- transfer layer, electron injecting layer, cathode construction organic luminescent device, the knot of the organic luminescent device of various structures also can be used Structure can also form the middle layer of one or two layers as needed.
As described above, the thickness of each organic matter layer formed according to the present invention can be adjusted according to required degree Section, it is preferable that be specially 10 to 1000nm, more specifically 20 to 150nm.
An example according to the present invention makes the outer of the electrode of the intervention of hole injection layer 200 in above-mentioned 1000 electrode of anode Side can form coating 3000.Also, in stating 2000 electrode of cathode, the outside for the electrode for intervening electron injecting layer 600 can Form coating 3000.Although not limited to this, above-mentioned coating 3000 can be formed by deposition procedures, can with 300 toThickness formed.
Also, although it is not shown, but an example according to the present invention, make the first order second electrode of above-mentioned coating intervention It can add to form the organic matter layer with multiple functions on outside.The shape immediately on first electrode (or second electrode) outer surface At coating, can add to form organic matter layer on above-mentioned coating.Also, in first electrode (or second electrode) outer surface The organic matter layer with multiple functions is formed, the coating containing the compound of the present invention can be formed on above-mentioned organic matter layer.
It is applicable that first embodiment of the invention recorded for the organic luminescent compounds of present embodiment Content, but can be not limited to this.
Hereinafter, embodiment through the invention carries out more specific description, the scope of the present invention is not limited to the present embodiment.
Embodiment
Intermediate synthesis
It, can synthetic intermediate OP by following reaction formula in order to synthesize purpose compound.
Production Example 1: intermediate (OP1)
In round-bottomed flask, by bromo- 9,9- diphenyl -9H- fluorenes (2-bromo-9, the 9-diphenyl-9H- of above-mentioned 2- Fluorene) 30.0g, aniline (aniline) 5.6g, t-BuONa 11g, Pd2(dba)3 2.8g、(t-Bu)3P 3.5ml dissolution After the toluene of 500ml, return stirring is carried out.Reaction is confirmed using thin-layered chromatography (TLC), and after adding water, knot Shu Fanying.Organic layer is extracted using methylcellulose (MC), and after being filtered under diminished pressure, is recrystallized to obtain The OP1 of 21.3g (yield 69%).
By the method for such as above-mentioned OP1, as shown in the following Table 1, using different initial substances, following OP2 is synthesized extremely OP11。
Table 1
Compound synthesis
Using above-mentioned intermediate OP1 to OP11, the following purpose compound 1 that synthesizes is to compound 15.
The synthesis of compound 1
In round-bottomed flask, by above-mentioned 9- (4- bromophenyl) -9H- carbazole (9- (4-bromop henyl) -9H- carbazole)3.0g、OP1 3.8g、t-BuONa 1.3g、Pd2(dba)30.35g、(t-Bu)3P 0.4ml is dissolved in 100ml Toluene after, carry out return stirring.Reaction is confirmed using thin-layered chromatography (TLC), and after adding water, reaction was completed. Organic layer is extracted using methylcellulose (MC), and after being filtered under diminished pressure, is recrystallized to obtain 3.7g (yield 61%) compound 1.M/z:650.27 (100.0%), 651.28 (53.4%), 652.28 (14.0%), 653.28 (2.4%)
The synthesis of compound 2
By the method for such as above compound 1, OP1 is replaced using OP2, synthesizes compound 2.(yield 65%) m/z: 726.30 (100.0%), 727.31 (59.9%), 728.31 (17.6%), 729.31 (3.4%)
The synthesis of compound 3
By the method for such as above compound 1,9- (bromo- [1,1'- the xenyl] -4- base of 4'-) -9H- carbazole (9- is used (4'-bromo- [1,1'-biphenyl] -4-yl) -9H-carbazole) replace 9- (4- bromophenyl) -9H- carbazole, it synthesizes Compound 3.(yield 60%) m/z:726.30 (100.0%), 727.31 (59.9%), 728.31 (17.6%), 729.31 (3.4%)
The synthesis of compound 4
By the method for such as above compound 1,9- (bromo- [1,1'- the xenyl] -4- base of 4'-) -9H- carbazole and OP2 are used To replace 9- (4- bromophenyl) -9H- carbazole and OP1, synthesis compound 4.(yield 78%) m/z:802.33 (100.0%), 803.34 (66.5%), 804.34 (22.2%), 805.34 (4.7%)
The synthesis of compound 5
By the method for such as above compound 1, OP1 is replaced using OP3, synthesizes compound 5.(yield 66%) m/z: 648.26 (100.0%), 649.26 (53.4%), 650.26 (14.2%), 651.27 (2.4%)
The synthesis of compound 6
By the method for such as above compound 1, OP1 is replaced using OP4, synthesizes compound 6.(yield 60%) m/z: 724.29 (100.0%), 725.29 (59.9%), 726.29 (17.8%), 727.30 (3.4%)
The synthesis of compound 7
By the method for such as above compound 1,9- (bromo- [1,1'- the xenyl] -4- base of 4'-) -9H- carbazole and OP3 are used To replace 9- (4- bromophenyl) -9H- carbazole and OP1, synthesis compound 7.(yield 62%) m/z:724.29 (100.0%), 725.29 (59.9%), 726.29 (17.8%), 727.30 (3.4%)
The synthesis of compound 8
By the method for such as above compound 1,9- (bromo- [1,1'- the xenyl] -4- base of 4'-) -9H- carbazole and OP4 are used To replace 9- (4- bromophenyl) -9H- carbazole and OP1, synthesis compound 8.(yield 60%) m/z:800.32 (100.0%), 801.32 (66.7%), 802.33 (21.7%), 803.33 (4.7%)
The synthesis of compound 9
By the method for such as above compound 1, OP1 is replaced using OP5, synthesizes compound 9.(yield 58%) m/z: 650.27 (100.0%), 651.28 (53.4%), 652.28 (14.0%), 653.28 (2.4%)
The synthesis of compound 10
By the method for such as above compound 1, OP1 is replaced using OP6, synthesizes compound 10.(yield 55%) m/z: 650.27 (100.0%), 651.28 (53.4%), 652.28 (14.0%), 653.28 (2.4%)
The synthesis of compound 11
By the method for such as above compound 1, OP1 is replaced using OP7, synthesizes compound 11.(yield 60%) m/z: 648.26 (100.0%), 649.26 (53.4%), 650.26 (14.2%), 651.27 (2.4%)
The synthesis of compound 12
By the method for such as above compound 1, OP1 is replaced using OP8, synthesizes compound 12.(yield 60%) m/z: 648.26 (100.0%), 649.26 (53.4%), 650.26 (14.2%), 651.27 (2.4%)
The synthesis of compound 13
By the method for such as above compound 1, OP1 is replaced using OP9, synthesizes compound 13.(yield 65%) m/z: 890.37 (100.0%), 891.37 (74.1%), 892.37 (27.2%), 893.38 (6.5%), 894.38 (1.1%)
The synthesis of compound 14
By the method for such as above compound 1, OP1 is replaced using OP10, synthesizes compound 14.(yield 60%) m/z: 888.35 (100.0%), 889.35 (74.3%), 890.36 (27.0%), 891.36 (6.5%), 892.36 (1.2%)
The synthesis of compound 15
By the method for such as above compound 1, OP1 is replaced using OP11, synthesizes compound 15.(yield 64%) m/z: 886.33 (100.0%), 887.34 (74.0%), 888.34 (27.6%), 889.34 (6.5%), 890.35 (1.1%)
Organic luminescent device manufacture
Embodiment 1
It, will as hole injection layer on the ito substrate for forming the reflecting layer comprising Ag HI01 be filmed, It willHATCN be filmed, as hole transporting layer willBPA be filmed after, as above-mentioned luminescent layer The BH01:BD01 of doping 3%, withIt is filmed.It then, will as electron supplying layerAlq3:Liq (1:1) After being filmed, LiF is depositedForm electron injecting layer.Then, as cathode, MgAg is deposited with the thickness of 15nm, On above-mentioned cathode, as coating, withThickness deposited compound 1.And by the device sealing (Encapsulation) In glove box, to be prepared for organic luminescent device.
Embodiment 2 is to embodiment 15
It in above-described embodiment 1, replaces compound 1 to form coating to compound 15 using compound 2 respectively, removes this Except, by method same as Example 1, it is prepared for organic luminescent device.
Comparative example 1 to 7
In above-described embodiment 1, compound 1 is replaced to form covering using compound R ef.1 to Ref.7 below respectively Layer, in addition to this, by method same as Example 1, is prepared for organic luminescent device.
The performance evaluation of organic luminescent device
Apply electricity using 2400 source measuring unit of Keithley (Kiethley 2400source measureme nt unit) Pressure is measured to inject electronics and hole using Konica Minolta (Konica Minolta) spectroradiometer (CS-2000) Thus under atmospheric conditions brightness when shining is measured for applying alive current density and brightness, to have rated reality The performance of the organic luminescent device of example and comparative example is applied, and the results are shown in table 2.
Table 2
Op.V mA/cm2 Cd/A QE (%) CIEy CIEy LT97
Embodiment 1 4.00 10 8.40 7.30 0.139 0.060 130
Embodiment 2 4.00 10 8.40 7.27 0.140 0.061 125
Embodiment 3 3.99 10 8.45 7.25 0.140 0.061 125
Embodiment 4 4.00 10 8.43 7.39 0.139 0.060 130
Embodiment 5 4.00 10 8.41 7.20 0.138 0.061 130
Embodiment 6 4.00 10 8.40 7.26 0.140 0.061 133
Embodiment 7 3.99 10 8.45 7.29 0.140 0.060 135
Embodiment 8 3.98 10 8.42 7.30 0.140 0.061 128
Embodiment 9 4.00 10 8.52 7.35 0.140 0.060 120
Embodiment 10 4.00 10 8.35 7.30 0.140 0.060 124
Embodiment 11 4.00 10 8.40 7.35 0.139 0.060 120
Embodiment 12 4.00 10 8.41 7.37 0.140 0.060 120
Embodiment 13 3.99 10 8.30 7.30 0.139 0.060 130
Embodiment 14 4.00 10 8.32 7.28 0.140 0.060 119
Embodiment 15 4.00 10 8.30 7.29 0.140 0.061 125
Comparative example 1 4.00 10 6.80 5.72 0.143 0.075 62
Comparative example 2 4.01 10 7.05 6.05 0.143 0.070 75
Comparative example 3 4.01 10 6.88 5.74 0.144 0.069 90
Comparative example 4 4.01 10 7.01 6.00 0.144 0.070 85
Comparative example 5 4.00 10 6.90 5.85 0.143 0.070 80
Comparative example 6 4.01 10 7.13 5.99 0.145 0.071 82
Comparative example 7 4.00 10 7.25 6.30 0.145 0.069 95
As shown in Table 2 above it is found that high external hair compared with comparative example 1 to comparative example 7, is presented in the embodiment of the present invention Light efficiency, excitation purity and service life are greatly improved.
More specifically, compared with comparative example 1 to 2, in the embodiment of the present invention, carbazole and 1 arylamine with fluorenyl It combines, improves refractive index, compared with comparative example 3 and 4, in the embodiment of the present invention, the nitrogen of carbazole connect base phase with arlydene In conjunction with maintaining big band gap, can have high refractive index, it can thus be appreciated that efficiency and chromaticity coordinates are improved.Also, with comparative example 5 and 6 It compares, the embodiment of the present invention has diaryl fluorene, has high Tg and Td under lower molecular weight, can inhibit the knot again of film Crystallization, thermal stability can be outstanding.Also, compared with comparative example 7, the embodiment of the present invention imports nitrogen-arlydene connection of carbazole The terminal part of base and the aryl fluorenes with conjugation, molecules align and intermolecular accumulation can become outstanding.
That is, using the coating formation compound of an example of the invention, when organic luminescent device forms coating, Confirm the external light emission efficiency that can improve organic luminescent device, chromaticity coordinates and service life.
The explanation of aforementioned present invention is for illustrative, and general technical staff of the technical field of the invention can manage Solution can be easily deformed in other specific ways in the case where not changing technical idea or essential feature of the invention.Therefore, It should be understood that various embodiments described above in all embodiments be it is illustrative, without being restrictive.For example, with single Each structural element that type illustrates is implemented dispersiblely, and equally, illustrating also can be with combination for multiple structural elements of dispersion Mode is implemented.
Range Representation, rather than above-mentioned detailed description, patent is claimed by appended patented invention in the scope of the present invention The meaning and range and the mode for having altered or deforming as derived from its equivalents for inventing claimed range should be by It is construed to be included within the scope of the present invention.

Claims (10)

1. a kind of coating, which is formed, uses compound, which is characterized in that indicated by following formula 1, be configured at organic luminescent device Electrode on the outside of:
Chemical formula 1
In the chemical formula 1,
Ar1For substituted or unsubstituted C6~50Arlydene or substituted or unsubstituted C5~50Heteroarylidene,
Ar2For substituted or unsubstituted C6~50Aryl or substituted or unsubstituted C5~50Heteroaryl,
Ar and Ar ' is separately substituted or unsubstituted C6~50Aryl or substituted or unsubstituted C5~50Heteroaryl Base, Ar can be connected with Ar ' and form ring, or can not also form ring,
L is Direct Bonding, substituted or unsubstituted C6~30Arlydene or substituted or unsubstituted C5~30Heteroarylidene,
R1To R4It is separately hydrogen, heavy hydrogen, substituted or unsubstituted C1~30Alkyl, substituted or unsubstituted C1~30Alkane Oxygroup, substituted or unsubstituted C2~30Alkenyl, substituted or unsubstituted C6~50Aryl or substituted or unsubstituted C5~50 Heteroaryl,
L, m and o is separately 0 or 1 to 4 integer, and n is 0 or integer of 1 to 3.
2. coating according to claim 1, which is formed, uses compound, which is characterized in that the compound is by following below formula 2 indicate:
Chemical formula 2
In the chemical formula 2,
The integer that p is 1 to 4.
3. coating according to claim 2, which is formed, uses compound, which is characterized in that the compound is by following below formula 3 or chemical formula 4 indicate:
In the chemical formula 3 or chemical formula 4,
R5And R6It is separately hydrogen, heavy hydrogen, substituted or unsubstituted C1~44Alkyl, substituted or unsubstituted C1~44Alkane Oxygroup, substituted or unsubstituted C2~44Alkenyl, substituted or unsubstituted C6~44Aryl or substituted or unsubstituted C5~44 Heteroaryl,
The integer that p is 1 to 4.
4. coating according to claim 3, which is formed, uses compound, which is characterized in that the compound is by following below formula 5 or chemical formula 6 indicate:
In the chemical formula 5 or chemical formula 6,
R5And R6It is separately hydrogen, heavy hydrogen, substituted or unsubstituted C1~44Alkyl, substituted or unsubstituted C1~44Alkane Oxygroup, substituted or unsubstituted C2~44Alkenyl, substituted or unsubstituted C6~44Aryl or substituted or unsubstituted C5~44 Heteroaryl,
The integer that p is 1 to 4, the integer that q is 0 or 1 to 4.
5. coating according to claim 1, which is formed, uses compound, which is characterized in that the Ar2It is substituted or unsubstituted Phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted xenyl, substituted or unsubstituted terphenyl, substitution or not Substituted phenanthryl, substituted or unsubstituted triphenyl, substituted or unsubstituted fluorenyl, two fluorenes of substituted or unsubstituted spiral shell or they Combination.
6. coating according to claim 1, which is formed, uses compound, which is characterized in that the L is Direct Bonding, sub- benzene Base, naphthylene, biphenylene, sub- triphenyl, fluorenylidene, dialkylfluorenylene, diaryl fluorenylidene, two fluorenylidene of spiral shell or they Combination.
7. coating according to claim 1, which is formed, uses compound, which is characterized in that the R1To R4Separately it is Hydrogen, phenyl, xenyl or naphthalene.
8. coating according to claim 1, which is formed, uses compound, which is characterized in that compound is used in the coating formation For one of following compound:
9. a kind of organic luminescent device characterized by comprising
First and second electrode；
Organic matter layer, on the inside of first and second described electrode；And
Coating, an electrode outer surface being configured in first and second described electrode, and containing in claim 1 to 8 Compound is used in described in any item coating formation.
10. organic luminescent device according to claim 9, which is characterized in that the coating with a thickness of 300 to
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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109651173A (en) * 2018-12-28 2019-04-19 武汉天马微电子有限公司 Compound, display panel and display device
CN111138342A (en) * 2018-11-05 2020-05-12 乐金显示有限公司 Novel compound and organic electroluminescent device comprising same
CN111341920A (en) * 2018-12-18 2020-06-26 固安鼎材科技有限公司 Organic electroluminescent device
US20210009518A1 (en) * 2019-07-12 2021-01-14 Semiconductor Energy Laboratory Co., Ltd. Organic Compound, Light-Emitting Device, Light-Receiving Device, Light-Emitting Apparatus, Light-Emitting Module, Electronic Device, and Lighting Device
CN112701238A (en) * 2021-01-06 2021-04-23 长春海谱润斯科技股份有限公司 Organic light-emitting device comprising covering layer and sealing layer
WO2021143246A1 (en) * 2020-01-19 2021-07-22 广州华睿光电材料有限公司 Organic electroluminescent device and fused ring-based aromatic amine compounds
CN115785063A (en) * 2018-09-17 2023-03-14 北京鼎材科技有限公司 Organic compound and organic electroluminescent device

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021167319A1 (en) * 2020-02-20 2021-08-26 주식회사 엘지화학 Organic light-emitting device

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101273008A (en) * 2005-09-30 2008-09-24 株式会社半导体能源研究所 Spirofluorene derivative, material for light-emitting element, light-emitting element, light-emitting device, and electronic device
WO2013109027A1 (en) * 2012-01-18 2013-07-25 덕산하이메탈(주) Compound, organic electronic element using same and electronic device thereof
KR20130106255A (en) * 2012-03-19 2013-09-27 덕산하이메탈(주) Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof
KR20150004099A (en) * 2013-07-02 2015-01-12 덕산하이메탈(주) An organic electronic element comprising a layer for improving light efficiency, and an electronic device comprising the same
KR20150031892A (en) * 2013-09-17 2015-03-25 덕산네오룩스 주식회사 Organic electronic element using a compound for organic electronic element, and an electronic device thereof
KR20150102734A (en) * 2014-02-28 2015-09-07 머티어리얼사이언스 주식회사 Organic compounds for an organic electroluminescent device and an organic electroluminescent device comprising the same
KR20150102733A (en) * 2014-02-28 2015-09-07 머티어리얼사이언스 주식회사 Organic compounds for forming capping layer of an organic electroluminescent device and an organic electroluminescent device comprising the same
WO2016003225A2 (en) * 2014-07-03 2016-01-07 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using same, and electronic device comprising same
US20160308162A1 (en) * 2015-04-16 2016-10-20 Samsung Display Co., Ltd. Organic light-emitting display apparatus and method of manufacturing the same

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20040098238A (en) 2003-05-14 2004-11-20 주식회사 대우일렉트로닉스 Filter assembly for oxygen generator

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101273008A (en) * 2005-09-30 2008-09-24 株式会社半导体能源研究所 Spirofluorene derivative, material for light-emitting element, light-emitting element, light-emitting device, and electronic device
WO2013109027A1 (en) * 2012-01-18 2013-07-25 덕산하이메탈(주) Compound, organic electronic element using same and electronic device thereof
KR20130106255A (en) * 2012-03-19 2013-09-27 덕산하이메탈(주) Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof
KR20150004099A (en) * 2013-07-02 2015-01-12 덕산하이메탈(주) An organic electronic element comprising a layer for improving light efficiency, and an electronic device comprising the same
KR20150031892A (en) * 2013-09-17 2015-03-25 덕산네오룩스 주식회사 Organic electronic element using a compound for organic electronic element, and an electronic device thereof
KR20150102734A (en) * 2014-02-28 2015-09-07 머티어리얼사이언스 주식회사 Organic compounds for an organic electroluminescent device and an organic electroluminescent device comprising the same
KR20150102733A (en) * 2014-02-28 2015-09-07 머티어리얼사이언스 주식회사 Organic compounds for forming capping layer of an organic electroluminescent device and an organic electroluminescent device comprising the same
WO2016003225A2 (en) * 2014-07-03 2016-01-07 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using same, and electronic device comprising same
US20160308162A1 (en) * 2015-04-16 2016-10-20 Samsung Display Co., Ltd. Organic light-emitting display apparatus and method of manufacturing the same

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115785063A (en) * 2018-09-17 2023-03-14 北京鼎材科技有限公司 Organic compound and organic electroluminescent device
US11545630B2 (en) 2018-11-05 2023-01-03 Lg Display Co., Ltd. Compound and organic electroluminescent device comprising the same
CN111138342A (en) * 2018-11-05 2020-05-12 乐金显示有限公司 Novel compound and organic electroluminescent device comprising same
CN111138342B (en) * 2018-11-05 2023-10-31 乐金显示有限公司 Novel compound and organic electroluminescent device comprising the same
CN111341920A (en) * 2018-12-18 2020-06-26 固安鼎材科技有限公司 Organic electroluminescent device
CN111341920B (en) * 2018-12-18 2024-01-30 固安鼎材科技有限公司 Organic electroluminescent device
CN109651173A (en) * 2018-12-28 2019-04-19 武汉天马微电子有限公司 Compound, display panel and display device
US20210009518A1 (en) * 2019-07-12 2021-01-14 Semiconductor Energy Laboratory Co., Ltd. Organic Compound, Light-Emitting Device, Light-Receiving Device, Light-Emitting Apparatus, Light-Emitting Module, Electronic Device, and Lighting Device
US11673863B2 (en) * 2019-07-12 2023-06-13 Semiconductor Energy Laboratory Co., Ltd. Organic compound, light-emitting device, light-receiving device, light-emitting apparatus, light-emitting module, electronic device, and lighting device
CN114514220A (en) * 2020-01-19 2022-05-17 广州华睿光电材料有限公司 Organic electroluminescent device and aromatic amine compound containing condensed ring
WO2021143246A1 (en) * 2020-01-19 2021-07-22 广州华睿光电材料有限公司 Organic electroluminescent device and fused ring-based aromatic amine compounds
CN112701238B (en) * 2021-01-06 2022-11-11 长春海谱润斯科技股份有限公司 Organic light-emitting device comprising covering layer and sealing layer
CN112701238A (en) * 2021-01-06 2021-04-23 长春海谱润斯科技股份有限公司 Organic light-emitting device comprising covering layer and sealing layer

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Application publication date: 20181211