CN107353212A - A kind of luminous organic material and its organic luminescent device - Google Patents

A kind of luminous organic material and its organic luminescent device Download PDF

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CN107353212A
CN107353212A CN201710627255.4A CN201710627255A CN107353212A CN 107353212 A CN107353212 A CN 107353212A CN 201710627255 A CN201710627255 A CN 201710627255A CN 107353212 A CN107353212 A CN 107353212A
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organic material
synthesis
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刘喜庆
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The invention discloses a kind of luminous organic material and its organic luminescent device, is related to organic optoelectronic materials technology.The present invention is by introducing class anthracene class rigid structure, show good heat endurance, and its diffraction is prepared into device, especially as the material of main part in organic electroluminescence device, possesses the features such as low driving voltage, high brightness, outstanding heat resistance and high efficiency, better than existing conventional OLED.

Description

A kind of luminous organic material and its organic luminescent device
Technical field
The present invention relates to organic photoelectrical material technical field, more particularly to a kind of luminous organic material and its organic illuminator Part.
Background technology
Organic electroluminescent LED (Organic Light Emitting Diode, OLED) has pure flat display (Cathode Ray Tube, CRT) and the overall merit of liquid crystal display (Liquid Crystal Display, LCD), is described as The FPD of 21 century and third generation Display Technique, it has also become a current international big study hotspot.
In general organic luminescent device (OLED) is the organic matter layer structure by being inserted between negative electrode, anode and negative electrode and anode Into, the composition of device is transparent ITO anode, hole injection layer (TIL), hole transmission layer (HTL), luminescent layer (EL), hole The negative electrodes such as barrier layer (HBL), electron transfer layer (ETL), electron injecting layer (EIL), LiAl are formed, and can omit 1~2 on demand has Machine layer.Voltage is formed between two electrodes of device, while being injected from cathode electronics, another side anode injection hole.Electronics and Hole returns to stable ground state and generates light transmitting in luminescent layer in conjunction with excitation state, excitation state is formed.Luminescent material is divided into glimmering Luminescent material and phosphor material, the forming method of luminescent layer are the methods that phosphor material (organic metal) is adulterated in fluorescent host material With the method for fluorescent host material doping fluorescent (organic matter for including nitrogen) dopant.It is to have to generally form emitting layer material The parts such as centerbody and benzene, biphenyl, naphthalene, heterocycle such as benzene, naphthalene, fluorenes, the fluorenes of spiral shell two, anthracene, miscellaneous anthracene pyrene, carbazole;Contraposition, meta, ortho position Binding site and the replacing structure such as cyano group, fluorine, methyl, the tert-butyl group.
At present, the research of electroluminescent organic material is carried out extensively in academia and industrial quarters, a large amount of function admirables Electroluminescent organic material be developed successively, but the technological industrialization process still faces many key issues how Design the more preferable material of new performance to be adjusted, be always those skilled in the art's urgent problem to be solved.
The content of the invention
It is an object of the invention to provide a kind of luminous organic material and its organic luminescent device.Organic hair provided by the invention Luminescent material thermal stability is high, preparation method is simple, is used and manufactured using the compound as the material of main part in luminescent layer Organic luminescent device, the advantages of driving voltage is low, luminous efficiency is high is shown, be the luminous organic material of function admirable.
The invention provides a kind of luminous organic material, and its general formula of molecular structure is as shown in I:
Wherein, R is selected from hydrogen atom, substituted or unsubstituted C1~C30Alkyl, substituted or unsubstituted C1~C30Alkane Epoxide, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C5~C30Heterocyclic radical, substituted or unsubstituted C10-C30One kind in condensed ring radical;X1~X17Independent is selected from C or N;Ar is selected from substituted or unsubstituted C6~C30Aryl, substitution Or unsubstituted C5~C30Heterocyclic radical, substituted or unsubstituted C10-C30One kind in condensed ring radical.
Preferably, the R is selected from hydrogen atom, substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C1~ C10Alkoxy, substituted or unsubstituted C6~C18Aryl, substituted or unsubstituted C5~C14Heterocyclic radical, substitution or do not take The C in generation10-C18One kind in condensed ring radical;X1~X17Independent is selected from C or N;Ar is selected from substituted or unsubstituted C6~C18Aryl, One kind in substituted or unsubstituted five-ring heterocycles, substituted or unsubstituted hexa-member heterocycle.
Preferably, for example following chemical formula 1- chemical formulas 9 of the molecular structure I of a kind of luminous organic material provided by the present invention In any one representation:
Preferably, the Ar is selected from phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, xenyl, terphenyl, indenyl, pyrroles Base, pyridine radicals, thienyl, furyl, indyl, quinolyl, isoquinolyl, benzothienyl, benzofuranyl, dibenzo furan Mutter base, dibenzothiophenes base, carbazyl or fluorenyl.
Further preferably, any one of a kind of luminous organic material of the present invention in chemical constitution as follows:
A kind of synthetic method of luminous organic material of the present invention, its syntheti c route are as follows:
Wherein, R is selected from hydrogen atom, substituted or unsubstituted C1~C30Alkyl, substituted or unsubstituted C1~C30Alkane Epoxide, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C5~C30Heterocyclic radical, substituted or unsubstituted C10-C30One kind in condensed ring radical;X1~X17Independent is selected from C or N;Ar is selected from substituted or unsubstituted C6~C30Aryl, substitution Or unsubstituted C5~C30Heterocyclic radical, substituted or unsubstituted C10-C30One kind in condensed ring radical.
Present invention also offers a kind of organic luminescent device, including first electrode, second electrode and it is placed in two electrode Between one or more organic compound layers, organic compound layer include hole injection layer, hole transmission layer, electronic blocking Layer, luminescent layer, hole blocking layer, electron transfer layer, at least one layer of electron injecting layer;At least one in the organic compound layer Layer includes luminous organic material of the present invention.
Preferably, the provided luminous organic material of its invention can be as the luminescent layer of organic luminescent device.
Beneficial effects of the present invention:
Present invention firstly provides a kind of luminous organic material, the luminous organic material has structure shown in formula I, passes through introducing The rigid structures such as class anthryl, good heat endurance is shown, and its diffraction is prepared into device, as organic electroluminescent Material of main part in device, the advantages of driving voltage is low, luminous efficiency is high is shown, better than existing conventional OLED.This hair It is bright that a kind of preparation method of luminous organic material is also provided, using the coupling reaction finished product of routine, the preparation method is simple, Raw material is easy to get, and disclosure satisfy that the needs of industrialization development.Luminous organic material of the present invention has good in OLED luminescent devices Application effect, there is good industrialization prospect.
Embodiment:
It is clearly and completely described below in conjunction with the technical scheme of the embodiment of the present invention, it is clear that described implementation Example only part of the embodiment of the present invention, rather than whole embodiments.Based on the embodiment in the present invention, art technology The every other embodiment that personnel are obtained under the premise of creative work is not made, belongs to protection scope of the present invention.
The invention provides a kind of luminous organic material, and its general formula of molecular structure is as shown in I:
Wherein, R is selected from hydrogen atom, substituted or unsubstituted C1~C30Alkyl, substituted or unsubstituted C1~C30Alkane Epoxide, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C5~C30Heterocyclic radical, substituted or unsubstituted C10-C30One kind in condensed ring radical;X1~X17Independent is selected from C or N;Ar is selected from substituted or unsubstituted C6~C30Aryl, substitution Or unsubstituted C5~C30Heterocyclic radical, substituted or unsubstituted C10-C30One kind in condensed ring radical.
Preferably, the R is selected from hydrogen atom, substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C1~ C10Alkoxy, substituted or unsubstituted C6~C18Aryl, substituted or unsubstituted C5~C14Heterocyclic radical, substitution or do not take The C in generation10-C18One kind in condensed ring radical;X1~X17Independent is selected from C or N;Ar is selected from substituted or unsubstituted C6~C18Aryl, One kind in substituted or unsubstituted five-ring heterocycles, substituted or unsubstituted hexa-member heterocycle.
According to the present invention, the substituted alkyl, substitution alkoxy, substitution aryl, substitution heterocyclic radical, substitution In condensed ring radical, the substituent independence is selected from alkyl, alkoxy, amino, halogen, cyano group, nitro, hydroxyl or sulfydryl.
Preferably, the molecular structure I of luminous organic material provided by the present invention is as in following chemical formula 1- chemical formulas 9 Any one representation:
Preferably, the Ar is selected from phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, xenyl, terphenyl, indenyl, pyrroles Base, pyridine radicals, thienyl, furyl, indyl, quinolyl, isoquinolyl, benzothienyl, benzofuranyl, dibenzo furan Mutter base, dibenzothiophenes base, carbazyl or fluorenyl.
Further preferably, any one of a kind of luminous organic material of the present invention in chemical constitution as follows:
Present invention also offers a kind of synthetic method of luminous organic material, its syntheti c route are as follows:
Wherein, R is selected from hydrogen atom, substituted or unsubstituted C1~C30Alkyl, substituted or unsubstituted C1~C30Alkane Epoxide, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C5~C30Heterocyclic radical, substituted or unsubstituted C10-C30One kind in condensed ring radical;X1~X17Independent is selected from C or N;Ar is selected from substituted or unsubstituted C6~C30Aryl, substitution Or unsubstituted C5~C30Heterocyclic radical, substituted or unsubstituted C10-C30One kind in condensed ring radical.
According to the present invention, the compound shown in intermediate A is prepared according to method as follows:
Under nitrogen protection, tri-butyl phosphine and palladium are catalyst, and tert-butyl group sodium alkoxide is a and primary under conditions of alkali Amine obtains intermediate A by Buchwald-Hartwig coupling reactions.
According to the present invention, target product I is prepared according to method as follows:
Under nitrogen protection, tri-butyl phosphine and palladium are catalyst, and tert-butyl group sodium alkoxide is under conditions of alkali, b is with Mesosome A obtains target product I by Buchwald-Hartwig coupling reactions.
The present invention special limitation no to above-mentioned reaction, it is using popular response well-known to those skilled in the art Can, the preparation method is simple to operate, is readily produced.
Present invention also offers a kind of organic luminescent device, including first electrode, second electrode and it is placed in two electrode Between one or more organic compound layers, organic compound layer include hole injection layer, hole transmission layer, electronic blocking Layer, luminescent layer, hole blocking layer, electron transfer layer, at least one layer of electron injecting layer;At least one in the organic compound layer Layer includes luminous organic material of the present invention.
Preferably, luminous organic material of the present invention can be as the luminescent layer in organic luminescent device.The device of use Part structure is preferably specially:Described luminous organic material compound/FIrpic is used as luminescent layer material, and Alq3 passes as electronics Defeated material, NPB is used as hole transmission layer material, to manufacture the organic luminescent device of construction same as below:ITO/NPB/ institutes The luminous organic material compound stated:FIrpic/Alq3/LiF/Al.The organic electroluminescence device can be used for FPD The application fields such as device, lighting source, direction board, signal lamp.
[embodiment 1] compound TM1 synthesis
The synthesis of intermediate A -1
By tri-butyl phosphine (3mL 1.0M toluene solution, 7.32mmol), palladium (0.4g, 1.83mmol) and uncle Sodium butoxide (22.8g, 238mmol) is added to 9- chrloroanthracenes (38.8g, 183mmol) and aniline (17.0g, 183mmol) in degassing first Solution in benzene (500mL), and the mixture is heated 2 hours under reflux.The reactant mixture is cooled to room temperature, used Dilution with toluene and via diatom
Soil filtering.The filtrate water is diluted, and extracted with toluene, and merges organic phase, it is carried out under vacuo Evaporation.The residue is filtered via silica gel, is recrystallized to give intermediate A -1 (41.8g, yield 85%).
Mass spectrum m/z:269.13 (calculated values:269.12).Theoretical elemental content (%) C20H15N:C,89.19;H,5.61; N, 5.20 actual measurement constituent contents (%):C,89.18;H,5.61;N,5.21.The above results confirm that it is target product to obtain product.
Compound TM1 synthesis
By tri-butyl phosphine (3mL 1.0M toluene solution, 7.32mmol), palladium (0.4g, 1.83mmol) and uncle Sodium butoxide (52.7g, 549mmol) exists added to 2- chrloroanthracenes (42.6g, 201mmol) and intermediate A -1 (49.2g, 183mmol) Solution in degassed toluene (500mL), and the mixture is heated 2 hours under reflux.The reactant mixture is cooled to Room temperature, filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and extracted with toluene, and is merged organic Phase, it is evaporated under vacuo.The residue is filtered via silica gel, is recrystallized to give target product TM1 (69.2g, yield 85%).
Mass spectrum m/z:445.19 (calculated values:445.18).Theoretical elemental content (%) C34H23N:C,91.65;H,5.20; N, 3.14 actual measurement constituent contents (%):C,91.66;H,5.21;N,3.13.The above results confirm that it is target product to obtain product.
[embodiment 2] compound TM2 synthesis
The synthesis of intermediate A -2
Change the 9- chrloroanthracenes in the synthesis of the intermediate A -1 of embodiment 1 into equimolar 10- chlorobenzenes simultaneously [g] quinoline, other steps It is rapid identical with the synthesis of the intermediate A -1 of embodiment 1, obtain intermediate A -2.Mass spectrum m/z:270.10 (calculated values:270.12). Theoretical elemental content (%) C19H14N2:C,84.42;H,5.22;N, 10.36 actual measurement constituent contents (%):C,84.43;H,5.22; N,10.35.The above results confirm that it is target product to obtain product.
Compound TM2 synthesis
Change the intermediate A -1 in the compound TM1 of embodiment 1 synthesis into equimolar intermediate A -2, other steps are equal It is identical with the compound TM1 of embodiment 1 synthesis, obtain target product TM2.Mass spectrum m/z:446.17 (calculated values:446.18).Reason Argument cellulose content (%) C33H22N2:C,88.76;H,4.97;N, 6.27 actual measurement constituent contents (%):C,88.77;H,4.96;N, 6.27.The above results confirm that it is target product to obtain product.
[embodiment 3] compound TM3 synthesis
The synthesis of intermediate A -3
Change the 9- chrloroanthracenes in the synthesis of the intermediate A -1 of embodiment 1 into equimolar 5- bromopyridines simultaneously [3,2-g] quinoline, Other steps are identical with the synthesis of the intermediate A -1 of embodiment 1, obtain intermediate A -3.Mass spectrum m/z:271.10 (calculated values: 271.11).Theoretical elemental content (%) C18H13N3:C,79.68;H,4.83;N, 15.49 actual measurement constituent contents (%):C, 79.68;H,4.84;N,15.48.The above results confirm that it is target product to obtain product.
Compound TM3 synthesis
Change the intermediate A -1 in the compound TM1 of embodiment 1 synthesis into equimolar intermediate A -3, other steps are equal It is identical with the compound TM1 of embodiment 1 synthesis, obtain target product TM3.Mass spectrum m/z:447.18 (calculated values:447.17).Reason Argument cellulose content (%) C32H21N3:C,85.88;H,4.73;N, 9.39 actual measurement constituent contents (%):C,85.89;H,4.73;N, 9.38.The above results confirm that it is target product to obtain product.
[embodiment 4] compound TM21 synthesis
Intermediate A -21-0 synthesis
Tetra-triphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) are added to phenyl boric acid The solution of (22.3g, 183mmol) and the chrloroanthracene of 9,10- bis- (45.8g, 185mmol) in degassing tetrahydrofuran (500mL), and The mixture is heated 4 hours under reflux.The reactant mixture is cooled to room temperature, rotation afterwards removes solvent.Via silicagel column Chromatography obtains intermediate A -21-0 (36.8g, theoretical value 70%).
Mass spectrum m/z:288.05 (calculated values:288.07).Theoretical elemental content (%) C20H13Cl:C,83.19;H,4.54; Cl, 12.28 actual measurement constituent contents (%):C,83.18;H,4.55;Cl,12.27.The above results confirm that obtain product produces for target Product.
The synthesis of intermediate A -21
Change the 9- chrloroanthracenes in the synthesis of the intermediate A -1 of embodiment 1 into equimolar intermediate A -21-0, other steps are equal It is identical with the synthesis of the intermediate A -1 of embodiment 1, obtain intermediate A -21.Mass spectrum m/z:345.16 (calculated values:345.15).Reason Argument cellulose content (%) C26H19N:C,90.40;H,5.54;N, 4.05 actual measurement constituent contents (%):C,90.41;H,5.54;N, 4.05.The above results confirm that it is target product to obtain product.
Compound TM21 synthesis
Change the intermediate A -1 in the compound TM1 of embodiment 1 synthesis into equimolar intermediate A -21, other steps It is identical with the compound TM1 of embodiment 1 synthesis, obtain target product TM21.Mass spectrum m/z:521.22 (calculated values: 521.21).Theoretical elemental content (%) C40H27N:C,92.10;H,5.22;N, 2.69 actual measurement constituent contents (%):C,92.11; H,5.21;N,2.68.The above results confirm that it is target product to obtain product.
[embodiment 5] compound TM25 synthesis
Change the 2- chrloroanthracenes in the compound TM1 of embodiment 1 synthesis into equimolar 3- chloro-acridines, other steps with reality It is identical to apply the compound TM1 of example 1 synthesis, obtains target product TM25.Mass spectrum m/z:522.22 (calculated values:522.21).It is theoretical Constituent content (%) C39H26N2:C,89.63;H,5.01;N, 5.36 actual measurement constituent contents (%):C,89.62;H,5.02;N, 5.36.The above results confirm that it is target product to obtain product.
[embodiment 6] compound TM67 synthesis
Intermediate A -67-0 synthesis
Change the phenyl boric acid in the intermediate A -21-0 of embodiment 4 synthesis into equimolar pyridine -4- boric acid, other steps It is identical with the intermediate A -21-0 of embodiment 4 synthesis, obtain intermediate A -67-0.Mass spectrum m/z:289.05 (calculated values: 289.07).Theoretical elemental content (%) C19H12ClN:C,78.76;H,4.17;Cl,12.24;N, 4.83 actual measurement constituent contents (%):C,78.76;H,4.16;Cl,12.25;N,4.83.The above results confirm that it is target product to obtain product.
The synthesis of intermediate A -67
Change the 9- chrloroanthracenes in the synthesis of the intermediate A -1 of embodiment 1 into equimolar intermediate A -67-0, other steps are equal It is identical with the synthesis of the intermediate A -1 of embodiment 1, obtain intermediate A -67.Mass spectrum m/z:346.16 (calculated values:346.15).Reason Argument cellulose content (%) C25H18N2:C,86.68;H,5.24;N, 8.09 actual measurement constituent contents (%):C,86.68;H,5.23;N, 8.09.The above results confirm that it is target product to obtain product.
Compound TM67 synthesis
Change the intermediate A -1 in the compound TM1 of embodiment 1 synthesis into equimolar intermediate A -67, other steps It is identical with the compound TM1 of embodiment 1 synthesis, obtain target product TM67.Mass spectrum m/z:524.22 (calculated values: 524.20).Theoretical elemental content (%) C37H24N4:C,84.71;H,4.61;N, 10.68 actual measurement constituent contents (%):C, 84.71;H,4.62;N,10.67.The above results confirm that it is target product to obtain product.
[embodiment 7] compound TM68 synthesis
Change the 2- chrloroanthracenes in the compound TM1 of embodiment 1 synthesis into equimolar 3- chloropyridines simultaneously [2,3-g] quinoline, Other steps are identical with the compound TM1 of embodiment 1 synthesis, obtain target product TM68.Mass spectrum m/z:524.21 (calculate Value:524.20).Theoretical elemental content (%) C37H24N4:C,84.71;H,4.61;N, 10.68 actual measurement constituent contents (%):C, 84.72;H,4.62;N,10.66.The above results confirm that it is target product to obtain product.
[embodiment 8] compound TM73 synthesis
The synthesis of intermediate A -73
Change the aniline in the synthesis of the intermediate A -1 of embodiment 1 into equimolar 4-aminopyridine, other steps with reality It is identical to apply the synthesis of the intermediate A -1 of example 1, obtains intermediate A -73.Mass spectrum m/z:270.10 (calculated values:270.12).Theoretical member Cellulose content (%) C19H14N2:C,84.42;H,5.22;N, 10.36 actual measurement constituent contents (%):C,84.43;H,5.22;N, 10.35.The above results confirm that it is target product to obtain product.
Compound TM73 synthesis
Change the intermediate A -1 in the compound TM1 of embodiment 1 synthesis into equimolar intermediate A -73, other steps It is identical with the compound TM1 of embodiment 1 synthesis, obtain target product TM73.Mass spectrum m/z:446.17 (calculated values: 446.18).Theoretical elemental content (%) C33H22N2:C,88.76;H,4.97;N, 6.27 actual measurement constituent contents (%):C,88.77; H,4.96;N,6.27.The above results confirm that it is target product to obtain product.
[embodiment 9] compound TM79 synthesis
The synthesis of intermediate A -79
Change the aniline in the synthesis of the intermediate A -1 of embodiment 1 into equimolar 4- tert-butyl groups aniline, other steps with The synthesis of the intermediate A -1 of embodiment 1 is identical, obtains intermediate A -79.Mass spectrum m/z:325.19 (calculated values:325.18).It is theoretical Constituent content (%) C24H23N:C,88.57;H,7.12;N, 4.30 actual measurement constituent contents (%):C,88.58;H,7.11;N, 4.31.The above results confirm that it is target product to obtain product.
Compound TM79 synthesis
Change the intermediate A -1 in the compound TM1 of embodiment 1 synthesis into equimolar intermediate A -79, other steps It is identical with the compound TM1 of embodiment 1 synthesis, obtain target product TM79.Mass spectrum m/z:501.27 (calculated values: 501.25).Theoretical elemental content (%) C38H31N:C,90.98;H,6.23;N, 2.79 actual measurement constituent contents (%):C,90.99; H,6.22;N,2.79.The above results confirm that it is target product to obtain product.
[contrast Application Example]
Transparent anode electrode ito substrate is cleaned by ultrasonic 15 minutes in isopropanol, and exposed 30 minutes under ultraviolet light, Then handled 10 minutes with plasma.The ito substrate after processing is then put into evaporated device.One layer of 70nm's of evaporation first NPB mixing evaporation TAPC/FIrpic, mixes as hole transmission layer, evaporation rate 0.1nm/s, followed by the evaporation of luminescent layer Miscellaneous concentration is 10wt%, evaporation rate 0.005nm/s, evaporation thickness 30nm, and 50nm Alq3 is then deposited as electronics Transport layer, evaporation rate 0.01nm/s, vacuum evaporation Al layers are as negative electrode, thickness 200nm on the electron transport layer.
[Application Example]
Transparent anode electrode ito substrate is cleaned by ultrasonic 15 minutes in isopropanol, and exposed 30 minutes under ultraviolet light, Then handled 10 minutes with plasma.The ito substrate after processing is then put into evaporated device.One layer of 70nm's of evaporation first The organic light emission material is deposited as hole transmission layer, evaporation rate 0.1nm/s, followed by the evaporation of luminescent layer, mixing in NPB Expect TM/FIrpic, doping concentration 10wt%, evaporation rate 0.005nm/s, evaporation thickness 30nm, 50nm is then deposited Alq3 as electron transfer layer, evaporation rate 0.01nm/s, vacuum evaporation Al layers are thick as negative electrode on the electron transport layer Spend for 200nm.
The electron luminescence characteristic of the organic luminescent device of above method manufacture represents in the following table:
Result above shows that luminous organic material of the invention is applied in organic luminescent device, especially as main body Material, the advantages of driving voltage is low, luminous efficiency is high is shown, be luminous organic material of good performance.
Obviously, the explanation of above example is only intended to help the method and its core concept for understanding the present invention.It should refer to Go out, under the premise without departing from the principles of the invention, can also be to this hair for the those of ordinary skill of the technical field Bright to carry out some improvement and modification, these are improved and modification is also fallen into the protection domain of the claims in the present invention.

Claims (8)

1. a kind of luminous organic material, it is characterised in that its general formula of molecular structure is as shown in I:
Wherein, R is selected from hydrogen atom, substituted or unsubstituted C1~C30Alkyl, substituted or unsubstituted C1~C30Alkoxy, Substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C5~C30Heterocyclic radical, substituted or unsubstituted C10-C30 One kind in condensed ring radical;X1~X17Independent is selected from C or N;Ar is selected from substituted or unsubstituted C6~C30Aryl, substitution do not take The C in generation5~C30Heterocyclic radical, substituted or unsubstituted C10-C30One kind in condensed ring radical.
2. a kind of luminous organic material according to claim 1, it is characterised in that R is selected from hydrogen atom, substitution or unsubstituted C1~C10Alkyl, substituted or unsubstituted C1~C10Alkoxy, substituted or unsubstituted C6~C18Aryl, substitution or Unsubstituted C5~C14Heterocyclic radical, substituted or unsubstituted C10-C18One kind in condensed ring radical;X1~X17It is independent selected from C or N;Ar is selected from substituted or unsubstituted C6~C18It is aryl, substituted or unsubstituted five-ring heterocycles, substituted or unsubstituted hexa-atomic miscellaneous One kind in ring.
A kind of 3. luminous organic material according to claim 1, it is characterised in that for example following chemical formulas of its molecular structure I Any one representation in 1- chemical formulas 9:
4. a kind of luminous organic material according to claim 1, it is characterised in that Ar is selected from phenyl, naphthyl, anthryl, phenanthrene Base, pyrenyl, xenyl, terphenyl, indenyl, pyrrole radicals, pyridine radicals, thienyl, furyl, indyl, quinolyl, isoquinolin Base, benzothienyl, benzofuranyl, dibenzofuran group, dibenzothiophenes base, carbazyl or fluorenyl.
5. a kind of luminous organic material according to claim 1, it is characterised in that in chemical constitution as follows Any one:
6. a kind of organic luminescent device, it is characterised in that the organic luminescent device includes negative electrode, anode and is placed in two electricity One or more organic compound layers between pole, described organic compound layer contain described in claim any one of 1-5 A kind of luminous organic material.
7. according to a kind of organic luminescent device described in claim 6, it is characterised in that the organic compound layer includes sky Cave implanted layer, hole transmission layer, in electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer extremely It is few one layer;A kind of luminous organic material of at least one layer described in containing claim any one of 1-5 in the organic compound layer.
8. according to a kind of organic luminescent device described in claim 7, it is characterised in that contain claims in luminescent layer A kind of luminous organic material described in 1-5.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111423426A (en) * 2019-12-26 2020-07-17 江西科技师范大学 Asymmetric 9- (N-tert-butyloxycarbonyl-2-pyrrolyl) -10-five-membered heterocyclic anthracene compound and application thereof
WO2023190987A1 (en) * 2022-03-31 2023-10-05 出光興産株式会社 Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100081846A1 (en) * 2007-01-26 2010-04-01 Doosan Corporation Asymmetric styryl derivatives and organic light emitting diode prepared using the same
CN101987822A (en) * 2009-08-07 2011-03-23 北京维信诺科技有限公司 Organic electroluminescent material and application thereof
JP2011091383A (en) * 2009-09-28 2011-05-06 Tdk Corp Compound for organic el element, and organic el element
CN106397405A (en) * 2016-09-18 2017-02-15 吉林奥来德光电材料股份有限公司 Anthracene-containing organic light-emitting compound and organic light-emitting device containing organic light-emitting compound

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100081846A1 (en) * 2007-01-26 2010-04-01 Doosan Corporation Asymmetric styryl derivatives and organic light emitting diode prepared using the same
CN101987822A (en) * 2009-08-07 2011-03-23 北京维信诺科技有限公司 Organic electroluminescent material and application thereof
JP2011091383A (en) * 2009-09-28 2011-05-06 Tdk Corp Compound for organic el element, and organic el element
JP5723127B2 (en) * 2009-09-28 2015-05-27 双葉電子工業株式会社 COMPOUND FOR ORGANIC EL ELEMENT AND ORGANIC EL ELEMENT
CN106397405A (en) * 2016-09-18 2017-02-15 吉林奥来德光电材料股份有限公司 Anthracene-containing organic light-emitting compound and organic light-emitting device containing organic light-emitting compound

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
AMERICAN CHEMICAL SOCIETY: "FIL REG", 《STN ON THE WEB》 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111423426A (en) * 2019-12-26 2020-07-17 江西科技师范大学 Asymmetric 9- (N-tert-butyloxycarbonyl-2-pyrrolyl) -10-five-membered heterocyclic anthracene compound and application thereof
WO2023190987A1 (en) * 2022-03-31 2023-10-05 出光興産株式会社 Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device

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