CN104017188A - Organic electroluminescence device main body material containing carbazole and triphenyl phosphine/phosphine oxide - Google Patents
Organic electroluminescence device main body material containing carbazole and triphenyl phosphine/phosphine oxide Download PDFInfo
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Abstract
The invention belongs to the field of organic electroluminescence and in particular relates to an organic electroluminescence device main body material containing carbazole and triphenyl phosphine/phosphine oxide. The main body material has a general structural formula as shown in the specification, in the formula, R1 is straight chain or branched alkyl chain with 1-12 carbon atoms, and R2 is phenyl, thienyl, alkyl substituted phenyl, alkyl substituted thienyl, alkyl, carbazolyl, alkyl substituted carbazolyl, fluorenyl, alkyl substituted fluorenyl, halogen atom or borate; x is more than 0 and less than 1, y is more than 0 and less than 1, and x+y=1; and n is a positive integer. According to the main body material, carbazole with good hole transmission performance is adopted as a hole transmission unit, and a triphenyl phosphine group or a triphenyl phosphine oxide group with good electron transmission capability is adopted as an electron transmission unit, so that the charge transfer balance is facilitated; and meanwhile, phosphorus atoms and modified 9-phenylcarbazole are favorable for reducing the conjugation degree of main polymer chains and increasing the triplet state energy level of polymers.
Description
Technical field
The present invention relates to technical field of organic electroluminescence, relate in particular to a class containing the organic electroluminescence device material of main part of carbazole and triphenyl phosphorus/phosphorus oxygen
Background technology
Organic Light Emitting Diode (OLED) is considered to illumination of future generation and full developing technology.At present, the luminescent device of the top efficiency of report is realized based on full phosphorescent emissions Organic Light Emitting Diode, higher spin-orbit coupling efficiency makes phosphorescent emissive material not only can utilize singlet exciton but also can utilize triplet excitons, thereby makes internal quantum efficiency can reach 100% in theory.But blue emitting phosphor luminescent device remains a bottleneck of restriction Organic Light Emitting Diode development at present.First, can be limited for the outstanding blue phosphorescent material of Organic Light Emitting Diode.At present, most popular blue light material is that two (4,6-difluorophenyl pyridine-N, C2) pyridine formyls close iridium (III) (FIrpic, triplet 2.62eV), but this material is sky blue.Secondly, the material of main part that can be used as Organic Light Emitting Diode blue phosphorescent is less.Blue phosphorescent material is not to be directly used in the emission layer that is prepared with OLED conventionally, but is dispersed in material of main part, so just can avoid triplet state cancellation and concentration quenching.This just requires the triplet state energy of material of main part and will could effectively be avoided energy to be returned to material of main part by phosphor material higher than the triplet of blue emitting phosphor material.With current most popular blue light dopant material FIrpic, necessarily require the triplet of material of main part could effectively suppress the passback of energy higher than 2.65eV.
Be prepared with the material of main part that OLED is conventional and comprise small molecules and polymer two classes.At present, the small molecules material of main part that high-level efficiency organic light emitting diode device mainly adopts.Although the efficiency of small molecules Organic Light Emitting Diode is generally higher than the efficiency of polymer LED, what prepare that small molecules Organic Light Emitting Diode often adopts is evaporation coating technique, and complex process time consumption and energy consumption and cost are higher.Solution method is considered to the most applicable technology that is prepared with on a large scale OLED of present stage, and this type of technical matters is simple and cost is low.But existing polymer main body material is usingd fluorenes or carbazole as structural unit, there is the low and unbalanced problem of carrier transport of triplet.
Given this, the polymer body material that high triplet was processed, had to synthetic applicable solution method is to solve Organic Light Emitting Diode bottleneck urgent problem.
Summary of the invention
In order to address the above problem, the object of the invention is to provide the compound of the organic electroluminescence device material of main part containing carbazole and triphenyl phosphorus/phosphorus-oxygen groups that is beneficial to the raising of triplet and the increase of stability.
Technical scheme of the present invention is: contain the compound of the organic electroluminescence device material of main part of carbazole and triphenyl phosphorus/phosphorus-oxygen groups, the structural formula of this compound is as follows:
The compound that contains the organic electroluminescence device material of main part of carbazole and phosphorus atom, the general structure of this polymkeric substance is:
,
,
or
;
Wherein, R in formula
1be 1 to 12 straight chain of carbon atom or the alkyl chain of branching, R
2for phenyl, the thienyl that phenyl, thienyl, alkyl replace, the fluorenyl that the carbazyl that alkyl, carbazyl, alkyl replace, fluorenyl, alkyl replace, halogen atom or boric acid ester; 0 < x < 1,0 < y < 1, and x+y=1; N value is positive integer.
Preferably, when x and y are 0.5, described compound has formula P1 structure:
P1
Preferably, when x and y are 0.5, described compound has formula P2 structure:
P2
The invention has the beneficial effects as follows, owing to adopting technique scheme, polymkeric substance of the present invention has the following advantages:
1) carbazole and triphenyl phosphorus/phosphorus-oxygen groups have higher hole and electronic transmission performance, and carbazole has higher triplet (3.01V);
2) introducing of triphenyl phosphorus/phosphorus-oxygen groups can form tetrahedral structure, effectively interrupts the conjugation of high polymer main chain, makes polymkeric substance have higher triplet, and makes high polymer main chain distortion, weakens intermolecular
π-
πintermolecular interaction, and hindered intermolecular accumulation and crystallization, increased the rigidity of molecule, can effectively increase the stability after film forming;
3) make, between side chain and main chain, certain distortion occurs introduce phenyl on the N of 9 of the carbazole groups of rigidity after, interrupt the interaction between side chain and main chain, and the conjugation between side chain and main chain is interrupted;
4) alkyl chain that phenyl connects can effectively increase the solvability of molecule, and provides site for accessing other groups.All these is conducive to the increase of the raising of triplet, deliquescent improvement and stability.
Accompanying drawing explanation
Fig. 1 is polymer P 1 and ultra-violet absorption spectrum and the fluorescence emission spectrum of P2 in dichloromethane solution and film.
Fig. 2 is polymer P 1 and the phosphorescent emissions of P2 in 2-methyltetrahydrofuran under 77K.
Fig. 3 is the cyclic voltammetry curve of polymer P 1 and P2.
Embodiment
Below by specific embodiment, the present invention is described further, and following specific embodiment is in order better to illustrate the present invention but not limit the present invention.
Embodiment 1:
M1's is synthetic
In 250ml flask, add iodophenol (22g, 100mmol), 1-bromooctane (25.09g, 130mmol), salt of wormwood (18g, 130mmol), acetone 100ml, reaction overnight under refluxing, then by solvent evaporate to dryness, the organic phase anhydrous sodium sulfate drying obtaining with dichloromethane extraction, obtain viscous liquid, through chromatography column, obtain the iodo-4-of 1-(octyloxy) benzene 33g (productive rate 99%).
1H?NMR?(400?MHz,?CDCl
3)?δ?=?7.52?(d,?
J=8.8,?2H),?6.65?(d,?
J=8.8,?2H),?3.88?(t,?
J=6.5,?2H),?1.90?–?1.78?(m,?2H),?1.41?(s,?2H),?1.27?(s,?8H),?0.87?(t,?
J=6.3,?3H).
By 3; 6-dibromo carbazole (10g; 28mmol), the iodo-4-of 1-(octyloxy) benzene (14.4g; 33mmol), cuprous iodide (285mg, 1.5mmol) Tripotassium phosphate (6.4g, 30mmol), trans 1; 6-cyclohexanediamine (3mol; 370ul) join in 250ml flask, add toluene (100 mL), under argon shield, reflux 40 hours.Stop heating, cool to room temperature, by solvent evaporate to dryness, with dichloromethane extraction, by organic phase, with after anhydrous sodium sulfate drying, solvent evaporated obtains M1 12g by column chromatography, and productive rate is 80.7%.
1H?NMR?(400?MHz,?CDCl
3)?δ?=?8.33?(d,?
J=20.4,?0.4H),?8.13?(d,?
J=18.9,?1.6H),?7.66?(d,?
J=23.7,?0.4H),?7.50?(d,?
J=24.2,1.6H),?7.33?(s,?1H),?7.24?(s,?1H),?7.15?(s,?1H),?7.07?(s,?1H),?4.27?(d,?
J=55.1,?1H),?3.96?(d,?
J=57.7,?1H),?1.83?(s,?2H),?1.49?(s,?1H),?1.26?(d,?
J=33.1,?9H),?0.87?(d,?
J=14.8,?3H)。
MS (MALDI-TOF): m/z C
26h
27br
2nO theoretical value 529.3; Measured value 529.1 (M
+).
Reaction formula is as follows:
M2's is synthetic
-78
ounder C, to Isosorbide-5-Nitrae-dibromobenzene (14.2g; in tetrahydrofuran solution 60mmol), drip n-Butyl Lithium (hexane solution of 1.6M) 26.25mL, under argon shield, be incubated 1.5 hours, then drip phenyl dichloro phosphine (5.9g; 4.5mL), dropwise after again-78
oClower reaction 1.5 hours, then transfers under room temperature and stirs and spend the night.By solvent evaporate to dryness, with dichloromethane extraction, use anhydrous sodium sulfate drying organic phase, except desolventizing, through chromatography column, obtain two (4-bromophenyl) (phenyl) phosphine 10g, productive rate 79.3%.
1H?NMR?(400?MHz,?CDCl
3)?δ?=?7.46?(d,?
J=7.7,?4H),?7.35?(d,?
J=4.1,?3H),?7.27?(d,?
J=7.5,?2H),?7.13?(t,?
J=7.6,?4H).?
13C?NMR?(101?MHz,?CDCl
3)?δ?=?135.98,?135.92,?135.86,?135.28,?135.07,?133.77,?133.57,?131.86,?131.79,?129.25,?128.83,?128.76,?123.69。
Two (4-bromophenyl) (phenyl) phosphine (8g, 18mmol) is dissolved in 100ml tetrahydrofuran (THF), is cooled to-78
oc, drips n-Butyl Lithium (hexane solution of 1.6M) 20mL, argon shield reaction 1.5h at this temperature; allow rear dropping 2-isopropoxy-4; 4,5,5-tetramethyl--1; 3; the assorted oxygen pentaborane (9.8mL, 45mmol) of 2-bis-, after dropwising; be badly in need of reaction 1.5h, then life to room temperature reaction spends the night.By tetrahydrofuran (THF) evaporate to dryness, by column chromatography, obtain white solid M2 7.2g, productive rate 77.8%.
1H?NMR?(400?MHz,?CDCl
3)?δ?=?7.86?(d,?
J=6.5,?0.6H),?7.73?(d,?
J=7.6,?3H),?7.68?–?7.58?(m,?1H),?7.55?–?7.47?(m,?0.3H),?7.42?(t,?
J=7.8,?0.3H),?7.31?–?7.25?(m,?7.8H),?1.31?(s,?24H).?
13C?NMR?(101?MHz,?CDCl
3)?δ?=?140.65,?140.53,?134.64,?134.58,?134.04,?133.85,?133.01,?132.82,?128.87,?128.56,?128.45,?83.81,?24.81。MS (MALDI-TOF): m/z C
30h
37b
2o
4p theoretical value 512.2; Measured value 513.2 (M
++ 1).
Reaction formula is as follows:
P1's is synthetic
By monomer M 1 (0.50g, 0.9450mmol), monomer M 2 (0.4860g, 0.9450mmol), wet chemical (2M, 5mL), a methyl tricapryl ammonium chloride (Aliquat 336), tetra-triphenylphosphine palladium (Pd (PPh
3)
4, 21.8mg) and 20ml toluene join in 50ml twoport flask, under argon shield, 90
oCunder lucifuge condition, react 48 hours.Then the deoxidation toluene solution (5mL) and the bromobenzene (0.5mL) that add phenylo boric acid (100mg), react respectively and within 12 hours, carry out end-blocking.Be cooled to room temperature, mixing liquid is imported in methyl alcohol, the precipitation of generation is used dichloromethane extraction after filtering, uses anhydrous sodium sulfate drying organic phase, concentrates and obtains, after suitable volume, with methanol extraction, being precipitated.Precipitation is used in apparatus,Soxhlet's and with normal hexane, methyl alcohol extracting, removes small molecules and catalyzer respectively after collecting, and finally uses trichloromethane extracting.The solution obtaining is concentrated rear with trichloromethane/methanol extraction, obtains white fiber shape solid 0.4g, productive rate 67%.
1H?NMR?(400?MHz,?CDCl
3)?δ?=?8.79?–?8.17?(m,?1H),?7.67?(s,?13H),?7.43?(s,?6H),?7.14?–?6.98?(m,?2H),?4.05?(s,?2H),?1.83?(s,?2H),?1.52?–?1.40?(m,?2H),?1.32?–?1.18?(m,?8H),?0.98?(t,?J=7.2,?3H)。
13c NMR (101 MHz, CDCl
3) δ=145.68,140.13,138.58,134.72,132.17,132.10,132.01,128.96,128.56,128.44,127.28,121.73,121.02,114.35,59.16,31.88,29.74,29.50,29.33,26.15,24.19,22.60,19.90,14.12,13.74. ultimate analysis: (C
44h
40nOP)
ntheoretical value C 83.94, and H 6.36, and N 2.22; Measured value C84.35, H 6.49, and N 1.97.
Reaction formula is as follows:
Embodiment 2:
M1's is synthetic
In 250ml flask, add iodophenol (22g, 100mmol), 1-bromooctane (25.09g, 130mmol), salt of wormwood (18g, 130mmol), acetone 100ml, reaction overnight under refluxing, then by solvent evaporate to dryness, the organic phase anhydrous sodium sulfate drying obtaining with dichloromethane extraction, obtain viscous liquid, through chromatography column, obtain the iodo-4-of 1-(octyloxy) benzene 33g (productive rate 99%).
1H?NMR?(400?MHz,?CDCl
3)?δ?=?7.52?(d,?
J=8.8,?2H),?6.65?(d,?
J=8.8,?2H),?3.88?(t,?
J=6.5,?2H),?1.90?–?1.78?(m,?2H),?1.41?(s,?2H),?1.27?(s,?8H),?0.87?(t,?
J=6.3,?3H).
By 3; 6-dibromo carbazole (10g; 28mmol), the iodo-4-of 1-(octyloxy) benzene (14.4g; 33mmol), cuprous iodide (285mg, 1.5mmol) Tripotassium phosphate (6.4g, 30mmol), trans 1; 6-cyclohexanediamine (3mol; 370ul) join in 250ml flask, add toluene (100 mL), under argon shield, reflux 40 hours.Stop heating, cool to room temperature, by solvent evaporate to dryness, with dichloromethane extraction, by organic phase, with after anhydrous sodium sulfate drying, solvent evaporated obtains M1 12g by column chromatography, and productive rate is 80.7%.
1H?NMR?(400?MHz,?CDCl
3)?δ?=?8.33?(d,?
J=20.4,?0.4H),?8.13?(d,?
J=18.9,?1.6H),?7.66?(d,?
J=23.7,?0.4H),?7.50?(d,?
J=24.2,1.6H),?7.33?(s,?1H),?7.24?(s,?1H),?7.15?(s,?1H),?7.07?(s,?1H),?4.27?(d,?
J=55.1,?1H),?3.96?(d,?
J=57.7,?1H),?1.83?(s,?2H),?1.49?(s,?1H),?1.26?(d,?
J=33.1,?9H),?0.87?(d,?
J=14.8,?3H)。
MS (MALDI-TOF): m/z C
26h
27br
2nO theoretical value 529.3; Measured value 529.1 (M
+).
Reaction formula is as follows:
M3's is synthetic
By the two 4-(4 of phenyl, 4,5,5-tetramethyl--1,3,2-dioxy boron penta ring-2-yl) Phenylphosphine (M2) (5.16g, 10mmol), Iron(III) chloride hexahydrate (305.4mg, 0.791mmol), thiocyanation iron (230.64mg, 2.37mmol), the iodine of catalytic amount joins in 100ml flask, add 60mL acetonitrile, under the continuous air-blowing of oxygen, 80
oc reaction 30 minutes, after be cooled to room temperature.By solvent evaporate to dryness, by column chromatography, obtain white solid M3 5g, productive rate 94%.
1H?NMR?(400?MHz,?CDCl
3)?δ?=?7.85?(d,?
J=5.7,?4H),?7.70?–?7.56?(m,?6H),?7.53?–?7.47?(m,?1H),?7.42?(d,?
J=6.7,?2H),?1.32?(s,?24H).?
13C?NMR?(101?MHz,?CDCl
3)?δ?=?135.57,?134.60,?134.55,?134.48,?132.14,?132.04,?131.97,?131.25,?131.15,?128.55,?128.43,?84.20,?24.87。MS (MALDI-TOF): m/z C
30h
37b
2o
5p theoretical value 530.2; Measured value 531.2 (M
++ 1).
P2's is synthetic
By monomer M 1 (0.5293g, 1.0mmol), monomer M 3 (0.5302g, 1.0mmol), wet chemical (2M, 5mL), a methyl tricapryl ammonium chloride (Aliquat 336), tetra-triphenylphosphine palladium (Pd (PPh
3)
4, 23.1mg) and 20ml toluene join in 50ml twoport flask, under argon shield, 90
oCunder lucifuge condition, react 48 hours.Then the deoxidation toluene solution (5mL) and the bromobenzene (0.5mL) that add phenylo boric acid (100mg), react respectively and within 12 hours, carry out end-blocking.Be cooled to room temperature, mixing liquid is imported in methyl alcohol, the precipitation of generation is used dichloromethane extraction after filtering, uses anhydrous sodium sulfate drying organic phase, concentrates and obtains, after suitable volume, with methanol extraction, being precipitated.Precipitation is used in apparatus,Soxhlet's and with normal hexane, methyl alcohol extracting, removes small molecules and catalyzer respectively after collecting, and finally uses trichloromethane extracting.The solution obtaining is concentrated rear with trichloromethane/methanol extraction, obtains white fiber shape solid 0.45g, productive rate 69.4%.
1H?NMR?(400?MHz,?CDCl
3)?δ?=?8.41?(s,?1H),?8.28?(d,?
J=18.7,?1H),?7.74?(d,?
J=51.7,?11H),?7.45?(dd,?
J=28.0,?20.1,?8H),?7.10?(s,?2H),?4.04?(s,?2H),?1.83?(s,?2H),?1.45?–?1.11?(m,?10H),?0.88?(s,?3H)。
13C?NMR?(101?MHz,?CDCl
3)?δ?=?145.60,?145.35,?144.08,?141.51,?132.91,?132.71,?132.13,?129.04,?128.67,?128.50,?128.29,?127.36,?126.98,?126.00,?119.11,?118.15,?115.81,?110.31,?68.29,?31.88,?29.38,?26.15,?22.68,?14.25。Ultimate analysis: (C
44h
40nO
2p) n theoretical value C 80.12, H 6.07, and N 2.12; Measured value C, 80.97; H 5.86; N 2.01.
Reaction formula is as follows:
Polymer performance characterizes:
The spectral quality of polymer P 1 and P2, electrochemical properties
1) spectral quality of compound P1 and P2
Fig. 1 is polymer P 1 and uv-absorbing and the fluorescence emission spectrum of P2 in methylene dichloride and film.The solution medium ultraviolet absorption peak of polymer P 1 and P2 is positioned at 225nm and 303nm left and right as shown in Figure 1, and maximum emission peak is respectively 387 and 393nm.Maximum absorption band in film lays respectively at 285 and about 303nm, and maximum emission peak is positioned at 410 and 428nm.By the absorption edge of P1 and P2 filminess, calculating that both are with is (E
g) be respectively 3.18 and 3.26 eV.Fig. 2, can be obtained the triplet (E of P1 and P2 by the phosphorescence spectrum under 77K
t) be that 2.72eV(triplet is according to formula E
t=1240/ λ calculates, and wherein λ is the peak position of first emission peak of phosphorescent emissions spectrum), the high triplet state of polymer P 1 and P2 can meet the requirement as organic electroluminescence device material of main part.
2) electrochemical properties of compound P1 and P2
Fig. 3 is the cyclic voltammetry curve of polymer P 1 and P2.Electrolyzer adopts three-electrode system, take platinum carbon dioxide process carbon electrode as working electrode, and platinum filament is to electrode, and silver/silver chloride electrode is reference electrode, and tetrabutyl ammonium hexafluorophosphate is as supporting electrolyte.Scanning speed be 100 millivolts per second.By cyclic voltammetry curve, show that the initial oxidation current potential of polymer P 1 and P2 is respectively 1.05 and 1.15V, calculate thus HOMO energy level be respectively-5.42 and-5.52V(ferrocene does interior mark, correcting potential 0.43V).According to HOMO and E
gobtain LUMO and be respectively-2.24 and-2.26 eV.
Claims (3)
1. containing the organic electroluminescence device material of main part of carbazole and triphenyl phosphorus/phosphorus oxygen, it is characterized in that, the general structure of this polymkeric substance is:
,
,
or
;
Wherein, R in formula
1be 1 to 12 straight chain of carbon atom or the alkyl chain of branching, R
2for phenyl, the thienyl that phenyl, thienyl, alkyl replace, the fluorenyl that the carbazyl that alkyl, carbazyl, alkyl replace, fluorenyl, alkyl replace, halogen atom or boric acid ester; 0 < x < 1,0 < y < 1, and x+y=1; N value is positive integer.
2. the organic electroluminescence device material of main part containing carbazole and triphenyl phosphorus/phosphorus oxygen according to claim 1, is characterized in that, works as x=0.5, y=0.5, and the structural formula of this material of main part (P1), as follows:
Formula P1.
3. the organic electroluminescence device material of main part containing carbazole and triphenyl phosphorus/phosphorus oxygen according to claim 1, is characterized in that, works as x=0.5, y=0.5, and the structural formula of this material of main part (P2), as follows::
Formula P2.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105524255A (en) * | 2014-09-30 | 2016-04-27 | 中国科学院长春应用化学研究所 | Polymer containing aryloxyphosphono or arylthiophosphono group, preparation method thereof and organic electroluminescent device |
| CN105778058A (en) * | 2015-11-26 | 2016-07-20 | 中国科学院长春应用化学研究所 | Conjugated polymer and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040202892A1 (en) * | 2003-04-08 | 2004-10-14 | Jsr Corporation | Polymer, polymer for forming organic electroluminescence device, polymer composition for organic electroluminescence device and organic electroluminescence device |
| CN103539819A (en) * | 2013-06-25 | 2014-01-29 | Tcl集团股份有限公司 | Bis-carbazolyl benzene compound, preparation method and application thereof and electroluminescent device |
-
2014
- 2014-06-23 CN CN201410283249.8A patent/CN104017188B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040202892A1 (en) * | 2003-04-08 | 2004-10-14 | Jsr Corporation | Polymer, polymer for forming organic electroluminescence device, polymer composition for organic electroluminescence device and organic electroluminescence device |
| CN103539819A (en) * | 2013-06-25 | 2014-01-29 | Tcl集团股份有限公司 | Bis-carbazolyl benzene compound, preparation method and application thereof and electroluminescent device |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105524255A (en) * | 2014-09-30 | 2016-04-27 | 中国科学院长春应用化学研究所 | Polymer containing aryloxyphosphono or arylthiophosphono group, preparation method thereof and organic electroluminescent device |
| CN105524255B (en) * | 2014-09-30 | 2018-02-13 | 中国科学院长春应用化学研究所 | Phosphono containing aryl oxide or polymer, its preparation method and the organic electroluminescence device of aryl phosphine sulfide acyl group group |
| CN105778058A (en) * | 2015-11-26 | 2016-07-20 | 中国科学院长春应用化学研究所 | Conjugated polymer and preparation method thereof |
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