CN108530469A - A kind of and fluorene compound and its organic electroluminescence device - Google Patents

A kind of and fluorene compound and its organic electroluminescence device Download PDF

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CN108530469A
CN108530469A CN201810533134.8A CN201810533134A CN108530469A CN 108530469 A CN108530469 A CN 108530469A CN 201810533134 A CN201810533134 A CN 201810533134A CN 108530469 A CN108530469 A CN 108530469A
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compound
substituted
fluorene compound
unsubstituted
organic
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张弘
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The present invention provides a kind of and fluorene compound and its organic electroluminescence device, belongs to organic photoelectrical material technical field.The compound has structure shown in formula (I), and in the present invention and fluorene compound has larger conjugate planes structure, so as to provide high electron mobility；Short of electricity subbase group purines structure is introduced, is more conducive to receive electronics, makes it have good transmission performance；Introduce bridged linkage, on the one hand can increase compound molecular weight, so as to get material have the function of high glass-transition temperature and can prevent crystallization, on the other hand make this kind of compound have certain distortion on stereoeffect, improve its film forming.It is used the compound as the material of main part in luminescent layer and manufactured organic electroluminescence device, shows the advantage that driving voltage is low, luminous efficiency is high, be the luminous organic material of function admirable.

Description

A kind of and fluorene compound and its organic electroluminescence device
Technical field
The present invention relates to organic photoelectrical material technical fields, and in particular to a kind of and fluorene compound and its organic electroluminescent Device.
Background technology
With the progress of information industry, traditional display has been unable to meet the requirement of people, such as：Cathode-ray tube (cathode ray tube, CRT) display volume is big, driving voltage is high；Liquid crystal display (liquid crystal Display, LCD) brightness is low, narrow viewing angle, operating temperature range are small；Plasma display (plasma display panel, PDP it) involves great expense, resolution ratio is not high, power consumption is big.
Organic electroluminescent LED (organic light-emitting diodes, OLEDs) is as a kind of completely new Display technology possesses the unmatched advantage of existing display technology in each performance, such as have it is all solid state, from main light emission, brightness Height, high-resolution, visual angle wide (170 degree or more), fast response time, thickness is thin, it is small, light-weight, can be used flexible base board, Low-voltage direct-current drives (3-10V), low in energy consumption, operating temperature range is wide etc. so that its application market is very extensive, such as illuminates System, communication system, car-mounted display, portable electronic device, fine definition show even military field.
Electroluminescent organic material is constantly realized in recent years to be broken through, and the progress to attract people's attention is achieved, to traditional Display material constitutes strong challenge.After flexible OLED commercialization, associated scientific research and business in the world at present Strength is all in the work for the development this respect done one's utmost.Although electroluminescent organic material research have been achieved with it is huge at Fruit, but OLED also has some urgent problems to be solved during commercialized.
Luminescent material is divided into fluorescent material and phosphor material, and the forming method of luminescent layer is that phosphorus is adulterated in fluorescent host material The method of method and fluorescent host material doping fluorescent (organic matter for including nitrogen) dopant of luminescent material (organic metal).It is common Material of main part can generally be divided into several, such as hole transport material of main part, electron-transport material of main part, bipolar material of main part, lazy Property material of main part, fluorescence complex material of main part and phosphorescent complexes material of main part.
In the organic luminescent device prepared using phosphor material, worked as mostly containing trianilino group material using TPD etc. Make the main body luminescent material of luminescent layer.However, the thermal stability of this kind of material is poor, lead to organic hair using phosphor material The service life of optical device is shorter, thus reduces the usage degree of such material.The better material of new performance how is designed to carry out It adjusts, is always those skilled in the art's urgent problem to be solved.
Invention content
The object of the present invention is to provide it is a kind of containing and fluorenes compound and its organic electroluminescence device, the present invention in and Fluorene compound has larger conjugate planes structure so as to provide high electron mobility；Short of electricity subbase group is introduced, it is more sharp In receiving electronics；Introduce bridged linkage, increase compound molecular weight, so as to get material have high glass-transition temperature and It can prevent the effect of crystallization.It is used the compound as the material of main part in luminescent layer and manufactured organic electroluminescence Part shows the advantage that driving voltage is low, luminous efficiency is high, is the luminous organic material of function admirable.
Present invention firstly provides a kind of and fluorene compounds, have structure shown in following general formula (I)：
A is indicated by general formula (II)：
Wherein R is selected from methyl, ethyl, propyl, isopropyl, butyl, tertiary butyl, n-hexyl, phenyl, xenyl or two R Connection cyclization；
Wherein X it is identical or different be selected from CR2Or N, wherein R2It is identical or different selected from H, halogen, substitution or Unsubstituted C1-C30 alkyl, the aryl of substituted or unsubstituted C6-C30, substituted or unsubstituted C3~C30 heteroaryl in One kind；
L is selected from the divalent of singly-bound, the divalent aryl of substituted or unsubstituted C6-C30, substituted or unsubstituted C3~C30 One kind in heteroaryl；
B is indicated by general formula (III)：
Wherein R1Selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, the aryl of substituted or unsubstituted C6-C30, substitution Or one kind in the heteroaryl of unsubstituted C3~C30.
Preferably, any one of the A in structure as follows：
Preferably, any one of the L in singly-bound or structure as follows：
Preferably, the B is indicated by general formula (III-a) or (III-b)：
Wherein R1Selected from hydrogen, C1~C4 alkyl or substituted or unsubstituted following group：Phenyl, naphthalene, anthryl, phenanthryl, Pyrenyl, xenyl, terphenyl, fluorenyl, two fluorenyl of spiral shell, carbazyl, triazine radical, dibenzothiophene, dibenzofuran group, quinoline Quinoline base or isoquinolyl.
Preferably, any one of described and fluorene compound in structure as follows：
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device include anode, cathode with And several organic function layers between the anode and the cathode, the organic function layer contain described and fluorenes Compound any one or at least two combination.
Preferably, the organic function layer includes luminescent layer, the luminescent layer include described and fluorene compound it is arbitrary It is a kind of or at least two combination.
Preferably, described and fluorene compound is used as material of main part in luminescent layer.
Beneficial effects of the present invention：
For the problems such as thermal stability for solving phosphorescent light body material in the prior art is poor, and service life is short, the present invention is first First provide it is a kind of containing and fluorene structured compound, the compound there is structure shown in formula (I).In the present invention and fluorene compound With larger conjugate planes structure, so as to provide high electron mobility；Electron deficient purine class formation is introduced, more conducively Receive electronics, makes it have good transmission performance；Bridged linkage is introduced, compound molecular weight on the one hand can be increased so that To material have the function of high glass-transition temperature and can prevent crystallization, on the other hand so that this analog derivative in sky Between have certain distortion in stereochemical structure, improve its film forming.The compound is used as the material of main part in luminescent layer and Manufactured organic electroluminescence device shows the advantage that driving voltage is low, luminous efficiency is high, is the organic light emission of function admirable Material.
Specific implementation mode
For a further understanding of the present invention, the preferred embodiment of the invention is described with reference to embodiment, still It should be appreciated that these descriptions are only the feature and advantage further illustrated the present invention, rather than to the claims in the present invention Limitation.
It should be noted that unless otherwise prescribed, the meaning of scientific and technical terminology used in the present invention and people in the art The meaning that member is generally understood is identical.
Alkyl of the present invention refers to alkyl made of minusing a hydrogen atom in alkane molecule, can be straight chain alkane Base, branched alkyl or naphthenic base, example may include methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, tertiary fourth Base, amyl, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Aryl of the present invention refer to aromatic hydrocarbon molecule aromatic core carbon on remove a hydrogen atom after, be left univalent perssad it is total Claiming, can be monocyclic aryl or fused ring aryl, example may include phenyl, xenyl, naphthalene, anthryl, phenanthryl or pyrenyl etc., but It is without being limited thereto.
Heteroaryl of the present invention refers to the total of the group that one or more aromatic core carbon are substituted by hetero atom in aryl Claim, the hetero atom includes but not limited to oxygen, sulphur, nitrogen or silicon atom, and the heteroaryl can be monocycle or condensed ring, and example can wrap Include pyridyl group, phenothiazinyl, phenoxazine base, pyrimidine radicals, benzo pyrimidine radicals, carbazyl, triazine radical, benzothiazolyl, benzo miaow Oxazolyl, acridinyl etc., but not limited to this.
Divalent aryl of the present invention refer to aromatic hydrocarbon molecule two aromatic core carbon on respectively remove a hydrogen atom after, be left Bivalent group general name, can be valentbivalent monocyclic aryl or divalent fused ring aryl, such as can be selected from phenylene, sub- biphenyl Base, sub- terphenyl, naphthylene, anthrylene, phenanthrylene, sub- pyrenyl, fluorenylidene or sub- benzo phenanthryl etc., but not limited to this.
Divalent heteroaryl radical of the present invention refers to that one or more of divalent aryl aromatic core carbon is replaced to obtain by hetero atom Group general name, the hetero atom includes but not limited to oxygen, sulphur or nitrogen-atoms, and the divalent heteroaryl radical can be valentbivalent monocyclic Heteroaryl or divalent fused ring heteroaryl, such as sub-pyridyl group, sub- quinolyl, sub- carbazyl, sub- thienyl, sub- benzo can be selected from Thienyl, furylidene, sub- benzofuranyl, sub- pyrimidine radicals, sub- benzo pyrimidine radicals, sub- imidazole radicals or sub- benzimidazolyl etc., But not limited to this.
Divalent aryl of the present invention refer to aromatic hydrocarbon molecule two aromatic core carbon on respectively remove a hydrogen atom after, be left Bivalent group general name, can be valentbivalent monocyclic aryl or divalent fused ring aryl, such as can be selected from phenylene, sub- biphenyl Base, sub- terphenyl, naphthylene, anthrylene, phenanthrylene, sub- pyrenyl, fluorenylidene or sub- benzo phenanthryl etc., but not limited to this.
Divalent heteroaryl radical of the present invention refers to that one or more of divalent aryl aromatic core carbon is replaced to obtain by hetero atom Group general name, the hetero atom includes but not limited to oxygen, sulphur or nitrogen-atoms, and the divalent heteroaryl radical can be valentbivalent monocyclic Heteroaryl or divalent fused ring heteroaryl, such as sub-pyridyl group, sub- quinolyl, sub- carbazyl, sub- thienyl, sub- benzo can be selected from Thienyl, furylidene, sub- benzofuranyl, sub- pyrimidine radicals, sub- benzo pyrimidine radicals, sub- imidazole radicals or sub- benzimidazolyl etc., But not limited to this.
In substituted alkyl of the present invention, substituted aryl, substituted heteroaryl etc., the substituent group can be independent Selected from D-atom, cyano, nitro, halogen atom, the alkyl of C1-C10, the alkoxy of C1-C10, the alkylthio group of C1-C10, C6- The heteroaryl of the aryl of C30, the aryloxy group of C6-C30, the arylthio of C6-C30, C3-C30, the silylation of C1~C30, C2~ The alkylamino radical of C10, aryl amine of C6~C30 etc., such as D-atom, cyano, nitro, halogen, methyl, ethyl, propyl, isopropyl Base, tertiary butyl, methoxyl group, methyl mercapto, phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, benzo phenanthryl, base, pyrene Base, fluorenyl, 9,9- dimethyl fluorenyl, benzyl, phenoxy group, thiophenyl, hexichol amido, dimethylamino, carbazyl, 9- phenyl clicks Oxazolyl, furyl, thienyl, triphenyl silicon substrate, trimethyl silicon substrate, trifluoromethyl, phenothiazinyl, phenoxazine group, acridinyl, piperazine Piperidinyl, pyridyl group, pyrazinyl, triazine radical, pyrimidine radicals etc., but not limited to this.
Present invention firstly provides a kind of and fluorene compounds, have the structural formula as shown in formula (I)：
A is indicated by general formula (II)：
Wherein R is selected from methyl, ethyl, propyl, isopropyl, butyl, tertiary butyl, n-hexyl, phenyl, xenyl or two R Connection cyclization；
Wherein X it is identical or different be selected from CR2Or N, wherein R2It is identical or different selected from H, halogen, substitution or Unsubstituted C1-C30 alkyl, the aryl of substituted or unsubstituted C6-C30, substituted or unsubstituted C3~C30 heteroaryl in One kind；
L is selected from the divalent of singly-bound, the divalent aryl of substituted or unsubstituted C6-C30, substituted or unsubstituted C3~C30 One kind in heteroaryl；
B is indicated by general formula (III)：
Wherein R1Selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, the aryl of substituted or unsubstituted C6-C30, substitution Or one kind in the heteroaryl of unsubstituted C3~C30.
Preferably, any one of the A in structure as follows：
Preferably, any one of the L in singly-bound or structure as follows：
Preferably, the B is indicated by general formula (III-a) or (III-b)：
Wherein R1Selected from hydrogen, C1~C4 alkyl or substituted or unsubstituted following group：Phenyl, naphthalene, anthryl, phenanthryl, Pyrenyl, xenyl, terphenyl, fluorenyl, two fluorenyl of spiral shell, carbazyl, triazine radical, dibenzothiophene, dibenzofuran group, quinoline Quinoline base or isoquinolyl.
Preferably, any one of described and fluorene compound in structure as follows：
It is enumerated above some specific structure types of the present invention and fluorene compound, but the invention is not limited in These listed chemical constitutions, every based on structure shown in formula (I), R, R1All should include for group as defined above Inside.
Of the present invention and fluorene compound, preparation method are as follows：
Dibromide containing A and the coupling of the boric acid ester compound containing L, by gained compound and containing the acid esterification of B Object is closed to be coupled to obtain described and fluorene compound.
The present invention limitation not special to above-mentioned reaction be using popular response well-known to those skilled in the art Can, the preparation method is easy to operate, is readily produced.
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device is those skilled in the art Known organic electroluminescence device, organic electroluminescence device of the present invention include anode, cathode and are located at Several organic function layers between the anode and cathode, the organic function layer includes described and fluorene compound is arbitrary It is a kind of or at least two combination.The organic function layer may include hole injection layer, hole transmission layer, electronic barrier layer, At least one layer in luminescent layer, hole blocking layer, electron transfer layer and electron injecting layer, the preferably described organic function layer include hair Photosphere, the luminescent layer include it is described and fluorene compound any one or at least two combination.More preferably described and fluorenes Compound is used as material of main part in luminescent layer.
The present invention is not particularly limited the source of the raw material employed in following embodiment, can be commercial product or It is prepared using preparation method well-known to those skilled in the art.
Embodiment 1：
The preparation of compound 1
The preparation of intermediate A
1-1 (31.81g, 100.00mmol) is added in the 50.0mL concentrated sulfuric acids, 2h is stirred at room temperature, finds reaction solution color Turn yellow, be slowly added in 300.0mL water, then has solid precipitation with sodium hydroxide neutralization reaction liquid, filtered after cooling down to neutral Solid 1-2 (21.18g, 75.56mmol).1-2 is dissolved in 150ml ethylene glycol, the hydrazine hydrate reflux that 40ml 30% is added is anti- It answers, during reaction solution cooling is fallen back, filtering precipitation obtains white solid 1-3 (14.29g, 56.12mmol).1-3 is dissolved in In 150mL toluene, 30g 1-4,1.5g four butyl bromation amines, reflux is added, cold filtration column chromatography obtains white powder (14.76g, 47.55mmol).Finally by its bromo, white powder is dissolved in 100.0mL chloroforms, it is anhydrous that 1.0g is added 20.0mL bromines are added dropwise in iron chloride, zero degree, and reaction finishes, washs multiple reaction solution with sodium sulfite saturated solution, be spin-dried for, obtain white Color solid intermediate A.
The preparation of compound 1-6
By bromide 1-6-a (4.26g, 20mmol), connection boric acid pinacol ester (6.22g, 24mmol), 1,1 '-bis- (hexichol Base phosphine)-ferrocene-palladium chloride (II) dichloromethane complex (0.49g, 0.6mmol), potassium acetate (5.90g, 60mmol) and 79ml toluene reacts 16 hours under reflux, cooling, and 26ml water is added, and stirs 30 minutes, isolates organic phase, pass through short diatom Native bed filtering, then evaporates organic solvent, gained crude product recrystallizes in heptane/toluene, obtains compound 1-6.
The preparation of compound 1
Under argon atmospher, by 1-6 (26.0g, 100mmol), intermediate A (23.30g, 50mmol), tetrakis triphenylphosphine palladium (0.35g, 0.3mmol), toluene (43ml), aqueous sodium carbonate (2M, 21ml) are added in flask, and back flow reaction 8 hours is cooling It to room temperature, is extracted with toluene, organic phase saturated common salt water washing, after organic phase drying, is purified with column chromatography, obtain chemical combination 1 21.55g of object, yield 75%.Mass spectrum m/z：574.69 (calculated values：574.68).Theoretical elemental content (%) C36H30N8：C, 75.24；H, 5.26；N, 19.50 actual measurement constituent contents (%)：C, 75.23；H, 5.27；N, 19.51.Above-mentioned confirmation obtains product For target product 1.
Embodiment 2：
The preparation of compound 8
The preparation of intermediate A
With in embodiment 1 intermediate A prepare it is identical.
The preparation of compound 8-6
By tri-tert-butylphosphine (toluene solution of the 1.0M of 4.4mL, 1.48g, 0.05mmol), palladium (0.4g, 1.83mmol) and sodium tert-butoxide (52.7g, 549mmol) is added to 8-6-a (14.61g, 73.42mmol) and 8-6-b The solution of (11.60g, 73.42mmol) in degassed toluene (500mL), and the mixture is heated 2 hours under reflux. The reaction mixture is cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, first is used in combination Benzene extracts, and merges organic phase, it is evaporated under vacuum.By the residue via silica gel (heptane/dichloromethane) It is filtered, and is crystallized from isopropanol.Obtain compound 8-6-c；By gained bromide 8-6-c (5.52g, 20mmol), connection Boric acid pinacol ester (6.22g, 24mmol), 1,1 '-bis- (diphenylphosphine)-ferrocene-palladium chloride (II) dichloromethane complexings Object (0.49g, 0.6mmol), potassium acetate (5.90g, 60mmol) and 79ml toluene react 16 hours under reflux, cooling, are added 26ml water stirs 30 minutes, isolates organic phase, filtered by short bed of diatomaceous earth, then evaporate organic solvent, gained crude product It is recrystallized in heptane/toluene, obtains compound 8-64.85g, yield 75%.
The preparation of compound 8
1-6 in embodiment 1 is replaced with into 8-6 as shown above, obtains compound 8.Mass spectrum m/z：700.81 (calculated values： 700.82).Theoretical elemental content (%) C44H32N10：C, 75.41；H, 4.60；N, 19.99 actual measurement constituent contents (%)：C, 75.42；H, 4.61；N, 19.98.It is target product 8 that above-mentioned confirmation, which obtains product,.
Embodiment 3：
The preparation of compound 23
The preparation of compound 23
1-4 in embodiment 1 is replaced with into 23-4 as shown above, 1-6 replaces with 23-6 as shown above, obtains compound 23.Mass spectrum m/z：1031.28 (calculated value：1031.26).Theoretical elemental content (%) C72H54N8：C, 83.86；H, 5.28；N, 10.87 actual measurement constituent contents (%)：C, 83.85；H, 5.29；N, 10.86.It is target product 23 that above-mentioned confirmation, which obtains product,.
Embodiment 4：
The preparation of compound 30
The preparation of compound 30-6
30-6-b's prepares same 8-6-c；Under argon atmospher, by obtained solid 30-6-b (6.64g, 15mmol), 30-6-c (4.05g, 14.3mmol), tetrakis triphenylphosphine palladium (0.35g, 0.3mmol), toluene (43ml), aqueous sodium carbonate (2M, It 21ml) is added in flask, back flow reaction 8 hours is cooled to room temperature, is extracted with toluene, and organic phase saturated common salt water washing has After machine is mutually dried, is purified with column chromatography, obtain bromide 30-6-d；30-6's prepares same 8-6.
The preparation of compound 30
1-4 in embodiment 1 is replaced with into 30-4 as shown above, 1-6 replaces with 30-6 as shown above, obtains compound 30.Mass spectrum m/z：783.00 (calculated values：783.01).Theoretical elemental content (%) C52H46N8：C, 79.77；H, 5.92；N, 14.31 actual measurement constituent contents (%)：C, 79.78；H, 5.93；N, 14.2.It is target product 30 that above-mentioned confirmation, which obtains product,.
Embodiment 5：
The preparation of compound 36
The preparation of compound 36
1-6 in embodiment 1 is replaced with into 36-6 as shown above, obtains compound 36.Mass spectrum m/z：851.03 (calculate Value：851.04).Theoretical elemental content (%) C58H42N8：C, 81.86；H, 4.97；N, 13.17 actual measurement constituent contents (%)：C, 81.85；H, 4.96；N, 13.18.It is target product 36 that above-mentioned confirmation, which obtains product,.
Embodiment 6：
The preparation of compound 43
The preparation of compound 43
1-6 in embodiment 1 is replaced with into 43-6 as shown above, obtains compound 43.Mass spectrum m/z：879.08 (calculate Value：879.09).Theoretical elemental content (%) C60H46N8：C, 81.98；H, 5.27；N, 12.75 actual measurement constituent contents (%)：C, 81.97；H, 5.28；N, 12.76.It is target product 43 that above-mentioned confirmation, which obtains product,.
Embodiment 7：
The preparation of compound 54
The preparation of compound 54
1-4 in embodiment 1 is replaced with into 54-4 as shown above, 1-6 replaces with 54-6 as shown above, obtains compound 54.Mass spectrum m/z：854.96 (calculated values：854.95).Theoretical elemental content (%) C52H42F4N8：C, 73.05；H, 4.95；F, 8.89；N, 13.11 actual measurement constituent contents (%)：C, 73.06；H, 4.96；F, 8.88；N, 13.12.Above-mentioned confirmation obtains product Target product 54.
Embodiment 8：
The preparation of compound 62
The preparation of compound 62
1-6 in embodiment 1 is replaced with into 62-6 as shown above, obtains compound 62.Mass spectrum m/z：726.89 (calculate Value：726.88).Theoretical elemental content (%) C48H38N8：C, 79.31；H, 5.27；N, 15.42 actual measurement constituent contents (%)：C, 79.31；H, 5.27；N, 15.42.It is target product 62 that above-mentioned confirmation, which obtains product,.
[comparison Application Example]
Transparent anode electrode ito substrate is cleaned each 15 minutes with deionized water, acetone, EtOH Sonicate respectively, is then existed It is cleaned 2 minutes in plasma cleaning device, dry and is evacuated to 5 × 10-5Pa.Then by treated, ito substrate steams Plating.One layer of HAT-CN is deposited first as hole transmission layer, evaporation rate 0.1nm/s, evaporation thickness 10nm.Followed by it sends out Light emitting layer material CBP/Ir (the ppy are deposited in the vapor deposition of photosphere, mixing3), as green light phosphorescence dopant material, doping is dense Degree is 5%, evaporation rate 0.005nm/s, evaporation thickness 30nm, the TPBI of 50nm is then deposited as electron transfer layer, Evaporation rate is 0.01nm/s, is used as cathode, thickness 30nm for vacuum evaporation Al layers on the electron transport layer.
[Application Example 1-8]
By the CBP compared in Application Example change into shown compound 1 in Application Example 1-8,8,23,30,36, 43、54、62。
Table 1 is compound prepared by the embodiment of the present invention and compares the characteristics of luminescence test of the luminescent device of substance preparation As a result.
The characteristics of luminescence of [table 1] luminescent device is tested
The above result shows that the compound of the present invention is applied to as green light material of main part in organic electroluminescence device, Luminous efficiency is high, is luminous organic material of good performance.
Although the present invention has carried out special description with exemplary embodiment, but it is understood that without departing from claim Defined by the case of spirit and scope of the invention, those of ordinary skill in the art can carry out various forms and details to it On change.

Claims (8)

1. a kind of and fluorene compound, which is characterized in that have structure shown in following general formula (I)：
A is indicated by general formula (II)：
Wherein R is selected from methyl, ethyl, propyl, isopropyl, butyl, tertiary butyl, n-hexyl, phenyl, xenyl or two R connections Cyclization；
Wherein X it is identical or different be selected from CR2Or N, wherein R2It is identical or different not take selected from H, halogen, substitution or The C1-C30 alkyl in generation, the aryl of substituted or unsubstituted C6-C30, substituted or unsubstituted C3~C30 heteroaryl in one Kind；
L is selected from the divalent heteroaryl of singly-bound, the divalent aryl of substituted or unsubstituted C6-C30, substituted or unsubstituted C3~C30 One kind in base；
B is indicated by general formula (III)：
Wherein R1Selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substitution or not One kind in the heteroaryl of substituted C3~C30.
2. according to claim 1 and fluorene compound, which is characterized in that the A is arbitrary in structure as follows It is a kind of：
3. according to claim 1 and fluorene compound, which is characterized in that the L is selected from singly-bound or structure as follows In any one：
4. according to claim 1 and fluorene compound, which is characterized in that the B is indicated by general formula (III-a) or (III-b)：
Wherein R1Selected from hydrogen, C1~C4 alkyl or substituted or unsubstituted following group：Phenyl, naphthalene, anthryl, phenanthryl, pyrenyl, Xenyl, terphenyl, fluorenyl, two fluorenyl of spiral shell, carbazyl, triazine radical, dibenzothiophene, dibenzofuran group, quinolyl Or isoquinolyl.
5. according to claim 1 and fluorene compound, which is characterized in that described and fluorene compound is selected from structure as follows In any one：
6. a kind of organic electroluminescence device, including anode, cathode and several between the anode and the cathode A organic function layer, which is characterized in that the organic function layer includes Claims 1 to 5 any one of them and fluorenes chemical combination Object any one or at least two combination.
7. a kind of organic electroluminescence device according to claim 6, which is characterized in that the organic function layer includes hair Photosphere, the luminescent layer include Claims 1 to 5 any one of them and fluorene compound any one or at least two group It closes.
8. a kind of organic electroluminescence device according to claim 6, which is characterized in that described and fluorene compound is shining It is used as material of main part in layer.
CN201810533134.8A 2018-05-29 2018-05-29 A kind of and fluorene compound and its organic electroluminescence device Withdrawn CN108530469A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108358918A (en) * 2018-04-25 2018-08-03 长春海谱润斯科技有限公司 A kind of pyrene derivatives and its organic electroluminescence device
CN108358919A (en) * 2018-04-25 2018-08-03 长春海谱润斯科技有限公司 A kind of phenanthrene derivative and its organic electroluminescence device
CN108440524A (en) * 2018-04-25 2018-08-24 长春海谱润斯科技有限公司 A kind of Sanya benzene derivative and its organic electroluminescence device

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CN107188873A (en) * 2017-06-12 2017-09-22 长春海谱润斯科技有限公司 A kind of phosphorescent light body material and organic luminescent device containing spirane structure

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CN107188873A (en) * 2017-06-12 2017-09-22 长春海谱润斯科技有限公司 A kind of phosphorescent light body material and organic luminescent device containing spirane structure

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108358918A (en) * 2018-04-25 2018-08-03 长春海谱润斯科技有限公司 A kind of pyrene derivatives and its organic electroluminescence device
CN108358919A (en) * 2018-04-25 2018-08-03 长春海谱润斯科技有限公司 A kind of phenanthrene derivative and its organic electroluminescence device
CN108440524A (en) * 2018-04-25 2018-08-24 长春海谱润斯科技有限公司 A kind of Sanya benzene derivative and its organic electroluminescence device

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