CN105932173B - A kind of phosphorescence host compound and its organic electroluminescence device based on fluorenes - Google Patents

A kind of phosphorescence host compound and its organic electroluminescence device based on fluorenes Download PDF

Info

Publication number
CN105932173B
CN105932173B CN201610364982.1A CN201610364982A CN105932173B CN 105932173 B CN105932173 B CN 105932173B CN 201610364982 A CN201610364982 A CN 201610364982A CN 105932173 B CN105932173 B CN 105932173B
Authority
CN
China
Prior art keywords
layer
compound
organic
fluorenes
electroluminescence device
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN201610364982.1A
Other languages
Chinese (zh)
Other versions
CN105932173A (en
Inventor
黄锦海
苏建华
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shanghai Taoe Chemical Technology Co Ltd
Original Assignee
Shanghai Taoe Chemical Technology Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shanghai Taoe Chemical Technology Co Ltd filed Critical Shanghai Taoe Chemical Technology Co Ltd
Priority to CN201610364982.1A priority Critical patent/CN105932173B/en
Publication of CN105932173A publication Critical patent/CN105932173A/en
Application granted granted Critical
Publication of CN105932173B publication Critical patent/CN105932173B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention provides a kind of compound based on fluorenes, the compound has preferable heat endurance, high-luminous-efficiency, high luminance purity, it can be used for making organic electroluminescence device, applied to organic solar batteries, Organic Thin Film Transistors or organophotoreceptorswith field.Present invention also offers a kind of organic electroluminescence device, it includes anode, cathode and organic layer, organic layer includes at least one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, and at least one layer includes the compound just like structural formula I in organic layer.

Description

A kind of phosphorescence host compound and its organic electroluminescence device based on fluorenes
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of phosphorescence host compound based on fluorenes and its Organic electroluminescence device, belongs to organic electroluminescence device display technology field.
Background technology
Organic electroluminescence device (OLEDs) is by spin coating or vacuum evaporation deposition one between two metal electrodes The device that layer organic material is prepared, a classical three layer organic electroluminescence device include hole transmission layer, luminescent layer And electron transfer layer.The electronics produced by cathode is followed to be incorporated in through electron transfer layer through hole transmission layer by the hole that anode produces Luminescent layer forms exciton, then shines.Organic electroluminescence device can be adjusted as desired by the material for changing luminescent layer Section launches the light of various needs.
Organic electroluminescence device has self-luminous, wide viewing angle, low energy consumption, efficiency as a kind of new Display Technique High, thin, rich in color, fast response time, Applicable temperature scope are wide, low driving voltage, can make flexible with it is transparent Display panel and the particular advantages such as environmental-friendly, can apply on flat-panel monitor and a new generation's illumination, can also conduct The backlight of LCD.
Since the invention at the bottom of the 1980s, organic electroluminescence device has industrially been applied, such as As screens such as camera and mobile phones, but current OLED device, since efficiency is low, it is wider that the factors such as service life is short restrict it General application, particularly large screen display, it is therefore desirable to improve the efficiency of device.And restrict one of key factor just It is the performance of the electroluminescent organic material in organic electroluminescence device.It is voltage-operated in application additionally, due to OLED device When, Joule heat can be produced so that organic material easily crystallizes, and have impact on service life and the efficiency of device, therefore, it is also desirable to Develop the electroluminescent organic material of stability and high efficiency.
Organic electrophosphorescenpolymer phenomenon, breaches theoretical limitation of the organic electroluminescent quantum efficiency less than 25%, and lifting is arrived 100% (Baldo M.A., Forrest S.R.Et al, Nature, 1998,395,151-154), its application also greatly carry The high efficiency of organic electroluminescence device.Usually, electroluminescent phosphorescence needs to use host-guest system technology, common to be used as phosphorus The CBP (4,4'-bis (9-carbazolyl)-biphenyl) of light material of main part has efficient and high triplet energy level, when its work For material of main part when, triplet energy state effectively can be transferred to object phosphorescent light-emitting materials from light emitting host material.But by Easily transmitted and the characteristic of the difficult flowing of electronics in the hole of CBP so that the charge unbalance of luminescent layer, as a result reduces the effect of device Rate.
The content of the invention
Present invention firstly provides a kind of pure hydrocarbon phosphorescence host compound based on fluorenes, it is with following structural formula I Compound：
Wherein, Ar1-Ar3Independently selected from C1-C12 substitutions either unsubstituted aryl, C1-C12 substitutions or unsubstituted Heteroaryl, further, wherein Ar1And Ar2It can be linked up with singly-bound.
Preferably, Ar1-Ar3Separately selected from phenyl, tolyl, xenyl, naphthyl.
It is further preferred that the compound based on fluorenes of the present invention is the compound of following structural 1-15：
。
The compound based on fluorenes of the present invention can be applied in organic electroluminescence device, organic solar batteries, organic Thin film transistor (TFT) or organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer Include at least one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer Layer, wherein at least one layer compound based on fluorenes contained as described in structural formula I in the organic layer：
Wherein Ar1-Ar3It is defined as described above.
Wherein organic layer is luminescent layer；
Or organic layer is luminescent layer and electron transfer layer；
Or organic layer is luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole transmission layer and luminescent layer；
Or organic layer is hole injection layer, hole transmission layer and luminescent layer；
Or organic layer is hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole injection layer, hole transmission layer, barrier layer, luminescent layer, electron transfer layer and electron injection Layer；
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and hole blocking layer；
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and hole blocking layer.
Preferably, layer where the compound based on fluorenes as described in structural formula I is luminescent layer.
Preferably, the compound based on fluorenes as described in structural formula I is the compound of structural formula 1-15.
When the compound based on fluorenes as described in structural formula I is used for luminescent device and prepares, it can be used alone, can also be with Other compounds are used in mixed way；The compound based on fluorenes as described in structural formula I can be used alone a kind of compound therein, The two or more compounds in structural formula I can also be used at the same time.
The organic electroluminescence device of the present invention, further preferred mode are that the organic electroluminescence device includes sun Contain at least one structure in pole, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and cathode, wherein luminescent layer The compound of Formulas I；It is further preferred that contain the compound of at least one structural formula 1-15 in luminescent layer.
The luminescent layer of organic electroluminescence device contains phosphorescence light emitting guest material and the compound conduct with structural formula I Material of main part, wherein Compounds of structural formula I are as material of main part, its concentration is the 20-99.9% of whole luminous layer weight, preferably 80-99%, more preferably 90-99%.
The gross thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
When having the compound of structural formula I using the present invention, can arrange in pairs or groups makes the organic electroluminescence device of the present invention With other materials, such as in hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer Deng, and obtain blue and green light, yellow light, feux rouges or white light.
The hole transmission layer and hole injection layer of organic electroluminescence device of the present invention, material requested have good hole Transmission performance, can effectively be transferred to hole on luminescent layer from anode.It can include other small molecules and macromolecule is organic Compound, includes but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine Class compound, six cyano group, six miscellaneous triphen (hexanitrilehexaazatriphenylene), 2,3,5,6- tetra- fluoro- 7,7', 8, Tetra- cyanogen dimethyl-parabenzoquinones (F4-TCNQ) of 8'-, polyvinyl carbazole, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of the organic electroluminescence device of the present invention, has the good characteristics of luminescence, can adjust as needed The scope of visible ray.Except the present invention have Compounds of structural formula I as phosphorescent light body material in addition to, can also arrange in pairs or groups other phosphorescence Material of main part, phosphorescence light emitting guest material can be included selected from least one of ruthenium, copper, rhodium, silver, iridium, platinum, gold and osmium metal Metal-organic complex.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires good electronic transmission performance, energy It is enough effectively electronics from cathode transport to luminescent layer in, there is very big electron mobility.Following compound can be selected, but It is not limited to this：Oxa- oxazole, thiazole compound, triazole compound, three nitrogen piperazine class compounds, triazine class chemical combination Thing, quinoline class compound, phenodiazine anthracene compound, siliceous heterocycle compound, quinolines, ferrosin class compound, Metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzimidazoles compound.
Electronics, effectively can be injected into organic layer by the electron injecting layer of organic electroluminescence device of the present invention from cathode In, it is mainly selected from the alkali metal either compound of alkali metal or compound or alkali selected from alkaline-earth metal or alkaline-earth metal Metal complex, can select following compound, but not limited to this：Alkali metal, alkaline-earth metal, rare earth metal, alkali metal Oxide either halide, the oxide of alkaline-earth metal or halide, the oxide of rare earth metal or halide, alkali metal Or the organic complex of alkaline-earth metal；Preferably lithium, lithium fluoride, lithia, lithium nitride, 8-hydroxyquinoline lithium, caesium, carbonic acid Caesium, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesia, these compounds can individually make With can also mixture use, can also be used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in the organic electroluminescence device of the present invention, can be steamed by vacuum vapour deposition, molecular beam It is prepared by the modes such as plating method, the dip coating for being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.It can make for metal motor Prepared with vapour deposition method or sputtering method.
Device experimental shows that compound based on fluorenes of the present invention as described in structural formula I, has preferable heat endurance, height Luminous efficiency, high luminance purity.The organic electroluminescence device made of the compound based on fluorenes is imitated with electroluminescent Rate is good and excitation purity is excellent and the advantages of long lifespan.
Brief description of the drawings
Fig. 1 is the mass spectrogram of compound 6；
Fig. 2 is the mass spectrogram of compound 7；
Fig. 3 is a kind of organic electroluminescence device structure diagram of the present invention,
Wherein, 110 glass substrate is represented as, 120 are represented as anode, and 130 are represented as hole injection layer, and 140 are represented as sky Cave transport layer, 150 are represented as luminescent layer, and 160 are represented as electron transfer layer, and 170 are represented as electron injecting layer, and 180 are represented as the moon Pole.
Embodiment
In order to describe the present invention in more detail, especially exemplified by example below, but not limited to this.
Embodiment 1
The synthesis of compound 1
The synthesis of intermediate 1-1
In the three-necked flask of 250mL, 9- phenyl -9- (4- bromophenyls)-fluorenes (15g, 38mmol), connection boric acid are sequentially added Pinacol ester (11.6g, 45mmol), potassium acetate (6g, 76mmol), two triphenylphosphine palladium of dichloro (200mg), dioxane (150mL), flow back 6h under nitrogen protection, removes solvent after cooling, adds water, is extracted with dichloromethane, dry, filters, concentration, Ethanol and recrystallize with dichloromethane are used again, obtain product 13g, yield 78%.
The synthesis of compound 1
Intermediate 1-1 (2.0g, 4.5mmol) is added in three-necked flask, to bromo-iodobenzene (0.56g, 2mmol), four triphens Base phosphine palladium (50mg), potassium carbonate (1.2g, 9mmol), tetrahydrofuran (20ml), water (10ml), under nitrogen protection, are heated to reflux 12 it is small when, cooling, is extracted with dichloromethane, dry, and concentration, crude product purifies to obtain 1g, yield 73% through column chromatography.
Embodiment 2
The synthesis of compound 6
Synthetic method is as the synthesis of compound 1, in addition to replacing to bromo-iodobenzene with a bromo-iodobenzene, yield 82%.
Embodiment 3
The synthesis of compound 7
The synthesis of intermediate 7-1
Intermediate 1-1 (10.0g, 22.5mmol) is added in three-necked flask, to bromo-iodobenzene (6.3g, 22.5mmol), four Triphenylphosphine palladium (150mg), potassium carbonate (6.2g, 45mmol), tetrahydrofuran (200ml), water (100ml), under nitrogen protection, Be heated to reflux 12 it is small when, cooling, is extracted with dichloromethane, dry, and concentration, crude product purifies to obtain 7.86g, yield through column chromatography 75%.
The synthesis of intermediate 7-2
Synthetic method is as with intermediate 1-1, except replacing compound 9- phenyl -9- (4- bromobenzenes with intermediate 7-1 Base) outside-fluorenes, yield 85%.
The synthesis of compound 7
In three-necked flask add intermediate 7-2 (1.0g, 1.9mmol), the bromo- 9,9- diphenylfluorenes of 2- (0.8g, 2mmol), tetra-triphenylphosphine palladium (50mg), potassium carbonate (0.56g, 4mmol), tetrahydrofuran (20ml), water (10ml), in nitrogen Under protection, be heated to reflux 12 it is small when, cooling, is extracted with dichloromethane, dry, and concentration, crude product purifies to obtain 1g through column chromatography, Yield 72%.
Embodiment 4
The synthesis of compound 8
Synthetic method is as with compound 7, except replacing bromo- 9, the 9- diphenylfluorenes of 2- with bromo- 9, the 9- diphenylfluorenes of 4- Outside, yield 87%.
Embodiment 5
The synthesis of compound 9
Synthetic method is as with compound 7, except being replaced with bromo- 9, the 9- spiro fluorenes of 4- outside bromo- 9, the 9- diphenylfluorenes of 2-, production Rate 64%.
Embodiment 6
The synthesis of compound 11
Synthetic method is as with compound 1, in addition to replacing to bromo-iodobenzene with adjacent bromo-iodobenzene, yield 86%.
Embodiment 7-12
The preparation of organic electroluminescence device
OLED is prepared using the compound of embodiment.
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share Department) pass through successively：Deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, the MnO of 3nm thickness is deposited on ITO3(molybdenum oxide) is hole injection layer 130.
Then, the CBP for 15nm thickness being deposited on hole injection layer is hole mobile material 140.
Then, the luminescent layer 150 of 15nm thickness is deposited on hole transmission layer, wherein, the compounds of this invention shines for main body Material, and with the Ir (ppy) of 8% weight ratio3Guest materials is adulterated as phosphorescence.
Then, the TPBi of 40nm thickness is deposited on the light-emitting layer as electron transfer layer 160.
Finally, evaporation 0.6nm LiF are electron injecting layer 170 and 150nm Al as device cathodes 180.
Prepared device (structure diagram is shown in Fig. 3) with Photo Research PR650 spectrometers measure 20mA/cm2Current density under voltage it is as shown in table 1 below.
Comparative example
In addition to luminescent layer replaces the compounds of this invention with BP, others are as embodiment 7-12.
Prepared device (structure diagram is shown in Fig. 3) with Photo Research PR650 spectrometers measure 20mA/cm2Current density under voltage it is as shown in table 1 below.
Table 1
Embodiment Compound Voltage (V) Glow color
7 1 6.5 Green light
8 6 6.2 Green light
9 7 6.1 Green light
10 8 6.0 Green light
11 9 6.0 Green light
12 11 6.6 Green light
Comparative example BF 7.2 Green light
As can be seen from the table, new organic materials of the invention are used for organic electroluminescence device, can reduce work Voltage, improves device efficiency, is the phosphorescent light body material with excellent performance.As described above, the compound of the present invention has height Stability, the organic electroluminescence device of preparation has high efficiency and optical purity.
The structural formula of compound described in device is as follows：
Preferred embodiment of the invention described in detail above.It should be appreciated that those of ordinary skill in the art without Need creative work to conceive according to the present invention and make many modifications and variations.Therefore, all technologies in the art Personnel are available by logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's idea Technical solution, all should be in the protection domain being defined in the patent claims.

Claims (7)

1. a kind of phosphorescence host compound based on fluorenes, it is characterised in that it is the compound with following structural formula I：
Wherein, Ar1-Ar3Independently selected from C1-C12 substitutions either unsubstituted aryl, C1-C12 substitutions or unsubstituted miscellaneous Aryl, wherein Ar1And Ar2It is not attached to or is linked up with singly-bound.
2. the phosphorescence host compound according to claim 1 based on fluorenes, it is characterised in that Ar1-Ar3Separately select From phenyl, tolyl, xenyl, naphthyl.
3. the phosphorescence host compound according to claim 1 based on fluorenes, it is characterised in that it is following structural 1-15 Compound：
。
4. a kind of organic electroluminescence device, it includes anode, cathode and organic layer, and organic layer includes luminescent layer, hole is injected At least one layer in layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, it is characterised in that described organic Contain the phosphorescence host compound based on fluorenes as claimed in claim 1 at least one layer in layer.
5. organic electroluminescence device according to claim 4, it is characterised in that the phosphorus based on fluorenes as described in structural formula I Layer where light host compound is luminescent layer.
6. organic electroluminescence device according to claim 4, it is characterised in that the phosphorus based on fluorenes as described in structural formula I Light host compound is used alone, or is used in mixed way with other compounds.
7. organic electroluminescence device according to claim 4, it is characterised in that the phosphorus based on fluorenes as described in structural formula I A kind of compound therein is used alone in light host compound, or uses the two or more compounds in structural formula I at the same time.
CN201610364982.1A 2016-05-27 2016-05-27 A kind of phosphorescence host compound and its organic electroluminescence device based on fluorenes Active CN105932173B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610364982.1A CN105932173B (en) 2016-05-27 2016-05-27 A kind of phosphorescence host compound and its organic electroluminescence device based on fluorenes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610364982.1A CN105932173B (en) 2016-05-27 2016-05-27 A kind of phosphorescence host compound and its organic electroluminescence device based on fluorenes

Publications (2)

Publication Number Publication Date
CN105932173A CN105932173A (en) 2016-09-07
CN105932173B true CN105932173B (en) 2018-04-24

Family

ID=56841580

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610364982.1A Active CN105932173B (en) 2016-05-27 2016-05-27 A kind of phosphorescence host compound and its organic electroluminescence device based on fluorenes

Country Status (1)

Country Link
CN (1) CN105932173B (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102077379A (en) * 2008-08-08 2011-05-25 默克专利有限公司 Organic electroluminescence device
CN103804244A (en) * 2012-11-08 2014-05-21 海洋王照明科技股份有限公司 Electronic input type red phosphorescent compound, preparation method thereof and organic electroluminescent device
CN104119290A (en) * 2013-04-25 2014-10-29 海洋王照明科技股份有限公司 Organic semiconductor material, preparation method thereof and electroluminescent device

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102124045B1 (en) * 2014-05-02 2020-06-18 삼성디스플레이 주식회사 Organic light emitting device

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102077379A (en) * 2008-08-08 2011-05-25 默克专利有限公司 Organic electroluminescence device
CN103804244A (en) * 2012-11-08 2014-05-21 海洋王照明科技股份有限公司 Electronic input type red phosphorescent compound, preparation method thereof and organic electroluminescent device
CN104119290A (en) * 2013-04-25 2014-10-29 海洋王照明科技股份有限公司 Organic semiconductor material, preparation method thereof and electroluminescent device

Also Published As

Publication number Publication date
CN105932173A (en) 2016-09-07

Similar Documents

Publication Publication Date Title
CN107987009A (en) A kind of carbazole derivates and application thereof and organic electroluminescence device
CN105153130B (en) Triazine derivative electron transport compound and its organic electroluminescence device
CN107954922A (en) A kind of two carbazole derivates of xenyl and application thereof and organic electroluminescence device
CN105601612B (en) Phosphorescence host compound containing indolyl radical and its organic electroluminescence device
CN105294663B (en) One kind containing pyridine compounds and its organic electroluminescence device
CN105061439B (en) A kind of organic electroluminescent compounds and its organic electroluminescence device
CN109053698A (en) A kind of aromatic amine compound and luminescent device containing dibenzofurans
CN109265450A (en) A kind of organic electroluminescent compounds and luminescent device of the aphthofurans containing benzo
CN107935999A (en) A kind of naphtho- benzofuran compound and application thereof and organic electroluminescence device
CN107935914A (en) A kind of two carbazole benzene derivatives and application thereof and organic electroluminescence device
CN107721979A (en) A kind of organic electroluminescent compounds and its organic electroluminescence device based on pyridine and triazine
CN106977514A (en) A kind of organic electroluminescent compounds and its luminescent device containing carbazole derivates
CN106831798B (en) Compound and its organic electroluminescence device containing five-membered ring structure
CN107417677A (en) A kind of carbazole pyridines organic electroluminescent compounds and its organic electroluminescence device
CN106749289B (en) A kind of organic electroluminescent compounds and its luminescent device with spiro structure
CN108912099A (en) A kind of compound containing triazine and carbazole and application thereof and organic electroluminescence device
CN105001229B (en) A kind of organic electroluminescent compounds and its device with spiro structure
CN105461707B (en) A kind of phosphorescence host compound and its organic electroluminescence device
CN106967065A (en) Organic electroluminescent compounds and its luminescent device containing two carbazyl phenyl groups
CN106554358B (en) A kind of organic electroluminescent compounds and its luminescent device with spiro structure
CN105218541A (en) A kind of phosphorescence host compound and organic electroluminescence device thereof
CN106543157B (en) A kind of electroluminescent organic material and its organic electroluminescence device
CN109705021A (en) A kind of organic electroluminescent compounds of the alkylnaphthalene containing cycloheptyl and application thereof and luminescent device
CN109232584A (en) A kind of organic electroluminescent compounds and luminescent device of the spiral shell containing benzimidazole
CN105017265B (en) A kind of organic electroluminescent compounds and its device containing heterocycle

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant