CN107382749A - The aromatic amine analog derivative and its organic luminescent device of a kind of class formation containing fluorenes - Google Patents

The aromatic amine analog derivative and its organic luminescent device of a kind of class formation containing fluorenes Download PDF

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CN107382749A
CN107382749A CN201710627371.6A CN201710627371A CN107382749A CN 107382749 A CN107382749 A CN 107382749A CN 201710627371 A CN201710627371 A CN 201710627371A CN 107382749 A CN107382749 A CN 107382749A
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substituted
aromatic amine
analog derivative
class formation
amine analog
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刘喜庆
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The present invention provides a kind of the aromatic amine analog derivative and its organic luminescent device of the class formation containing fluorenes, is related to organic optoelectronic materials technology.By introducing fluorenes class and benzofluoranthrene class rigid structure, improve the aromatic amine analog derivative thermal stability obtained by the present invention.For preparing organic luminescent device, especially as the hole mobile material in organic luminescent device, possesses the features such as high luminous efficiency, outstanding heat resistance, long-life.

Description

The aromatic amine analog derivative and its organic luminescent device of a kind of class formation containing fluorenes
Technical field
The present invention relates to the aromatic amine of organic photoelectrical material technical field, more particularly to a kind of class formation containing fluorenes to derive Thing and its organic luminescent device.
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.
As the hole transmission layer in OLED, its basic role is to improve hole efficiency of transmission in the devices, and by electricity Son is effectively blocked in luminescent layer, realizes the maximum compound of carrier；Reduce energy wall of the hole in injection process simultaneously Build, the injection efficiency in hole is improved, so as to improve the brightness of device, efficiency and life-span.Therefore for organic electroluminescent hole Transmission material, to meet it is following some：(1) pin-free homogeneous amorphous thin film can be formed；(2) what is formed is amorphous thin Film has good heat endurance；(3) there is suitable HOMO orbital energy levels, to ensure hole in electrode/organic layer and have Being efficiently injected into and transmitting between machine layer/organic layer interface：(4) there is very high hole mobility.
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.Organic hole passes The research of defeated material focuses on improving the film forming of material and the heat endurance of film.
The content of the invention
It is an object of the invention to provide a kind of aromatic amine analog derivative of class formation containing fluorenes.Class containing fluorenes provided by the invention The aromatic amine analog derivative thermal stability of structure is high, preparation method is simple, makes using the compound as hole mobile material With and manufactured organic luminescent device, luminous efficiency height is shown, the advantages of long lifespan.
The invention provides a kind of aromatic amine analog derivative of class formation containing fluorenes, its general formula of molecular structure is as shown in I：
Wherein, Ar is selected from C6~C50 substituted or unsubstituted aryl, C6~C50 substituted or unsubstituted heteroaryl In one kind；R1 is selected from hydrogen atom, C1~C10 substituted or unsubstituted alkyl, C6~C50 substituted or unsubstituted aryl In one kind；Substituted or unsubstituted alkyl of the R2 selected from C1~C10, C6~C50 substituted or unsubstituted aryl in one Kind.
Preferably, Ar is selected from C6~C30 substituted or unsubstituted aryl, C6~C19 substituted or unsubstituted heteroaryl One kind in base；R1Selected from hydrogen atom, C1~C6 substituted or unsubstituted alkyl, C6~C30 substituted or unsubstituted virtue One kind in base；R2Substituted or unsubstituted alkyl selected from C1~C4, one in C6~C15 substituted or unsubstituted aryl Kind.
Preferably, the Ar be selected from phenyl, naphthyl, anthryl, xenyl, terphenyl, pyrrole radicals, pyridine radicals, thienyl, Furyl, indyl, quinolyl, isoquinolyl, benzothienyl, benzofuranyl, dibenzofuran group, dibenzothiophenes base Or carbazyl.
Further preferably, the aromatic amine analog derivative of the class formation containing fluorenes is in structure shown in following TM1~TM65 Any one：
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 the aromatic amine analog derivative of the class formation of the present invention containing fluorenes.
Preferably, the aromatic amine analog derivative for the class formation containing fluorenes that its invention is provided can be as organic luminescent device Hole transmission layer.
Beneficial effects of the present invention：
Present invention firstly provides a kind of aromatic amine analog derivative of class formation containing fluorenes, the aromatic amine analog derivative has Structure shown in formula I, by introducing the rigid structure such as fluorenes class and benzofluoranthrene class, the compound that the present invention obtains is set to show well Heat endurance and film forming, and its diffraction is prepared into device, as the hole transport material in organic electroluminescence device Material, the advantages of showing luminous efficiency high, long lifespan, better than existing conventional OLED.The present invention also provides a kind of organic hair The preparation method of luminescent material, 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 application effect in OLED luminescent devices, has good 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 necessary to illustrate, unless State otherwise, the implication of scientific and technical terminology used in the present invention is identical with the implication that those skilled in the art are generally understood.
Alkyl of the present invention refers to minus the alkyl that a hydrogen atom forms in alkane molecule, and it can be straight chain alkane Base, branched alkyl, cycloalkyl, example may include methyl, ethyl, propyl group, isopropyl, normal-butyl, isobutyl group, sec-butyl, tertiary fourth Base, amyl group, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Aryl of the present invention refers to after removing a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule, is left the total of univalent perssad Claiming, it can be monocyclic aryl or fused ring aryl, and example may include phenyl, xenyl, naphthyl, anthryl, phenanthryl or pyrenyl etc., but Not limited to this.
Heteroaryl of the present invention refers to the group that one or more of aryl aromatic core carbon substitutes to obtain by hetero atom General name, the hetero atom include but is not limited to oxygen, sulphur or nitrogen-atoms, and the heteroaryl can be bicyclic heteroaryl or condensed ring heteroaryl Base, example may include pyridine radicals, pyrrole radicals, pyridine radicals, thienyl, furyl, indyl, quinolyl, isoquinolyl, benzo thiophene Fen base, benzofuranyl, dibenzofuran group, dibenzothiophenes base, carbazyl etc., but not limited to this.
The invention provides a kind of aromatic amine analog derivative of class formation containing fluorenes, its general formula of molecular structure is as shown in I：
Wherein, Ar is selected from C6~C50 substituted or unsubstituted aryl, C6~C50 substituted or unsubstituted heteroaryl In one kind；R1Selected from hydrogen atom, C1~C10 substituted or unsubstituted alkyl, C6~C50 substituted or unsubstituted aryl In one kind；R2Substituted or unsubstituted alkyl selected from C1~C10, one in C6~C50 substituted or unsubstituted aryl Kind.
Preferably, Ar is selected from C6~C30 substituted or unsubstituted aryl, C6~C19 substituted or unsubstituted heteroaryl One kind in base；R1Selected from hydrogen atom, C1~C6 substituted or unsubstituted alkyl, C6~C30 substituted or unsubstituted virtue One kind in base；R2Substituted or unsubstituted alkyl selected from C1~C4, one in C6~C15 substituted or unsubstituted aryl Kind.
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 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, a kind of aromatic amine analog derivative of class formation containing fluorenes of the present invention is selected from following TM1~TM65 Any one in shown structure：
Present invention also offers a kind of synthetic method of the aromatic amine analog derivative of class formation containing fluorenes, its syntheti c route is such as Under：
Wherein, Ar is selected from C6~C50 substituted or unsubstituted aryl, C6~C50 substituted or unsubstituted heteroaryl In one kind；R1Selected from hydrogen atom, C1~C10 substituted or unsubstituted alkyl, C6~C50 substituted or unsubstituted aryl In one kind；R2Substituted or unsubstituted alkyl selected from C1~C10, one in C6~C50 substituted or unsubstituted aryl Kind.
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 under conditions of alkali, benzo is glimmering Anthracene obtains intermediate A with primary amine 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 bromo fluorenes under conditions of alkali Class compound obtains target product I with intermediate A 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 the aromatic amine analog derivative of the class formation of the present invention containing fluorenes.
Preferably, the aromatic amine analog derivative of the class formation of the present invention containing fluorenes can be as in organic luminescent device Hole transmission layer.The device architecture of use is preferably specially：TAPC/FIrpic is used as luminescent layer material, and Alq3 passes as electronics Defeated material, the aromatic amine analog derivative of the class formation containing fluorenes is used as hole transmission layer material, to have manufactured following phase Syntectonic organic luminescent device：Aromatic amine analog derivative/TAPC of the class formation containing fluorenes described in ITO/:FIrpic/Alq3/ LiF/Al.The organic electroluminescence device can be used for the application fields such as flat-panel monitor, 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) added to 3- bromobenzenes simultaneously [k] fluoranthene (60.3g, 183mmol) and aniline (17.0g, 183mmol) the solution in degassed toluene (500mL), and the mixture is heated 2 hours under reflux.The reaction is mixed Compound is cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and extracted with toluene, and And merge organic phase, it is evaporated under vacuo.The residue is filtered via silica gel, is recrystallized to give intermediate A-1 (53.3g, yield 85%).
Mass spectrum m/z：343.13 (calculated values：343.14).Theoretical elemental content (%) C26H17N：C,90.93；H,4.99； N, 4.08 actual measurement constituent contents (%)：C,90.94；H,4.98；N,4.08.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) added to bromo- 9, the 9- dimethyl fluorenes (54.6g, 201mmol) of 2- and intermediate A -1 (62.7g, 183mmol) the solution in degassed toluene (500mL), and the mixture is heated 2 hours under reflux.The reaction is mixed Compound is cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and extracted with toluene, and And merge organic phase, it is evaporated under vacuo.The residue is filtered via silica gel, is recrystallized to give target production Thing TM1 (69.2g, yield 85%).
Mass spectrum m/z：535.24 (calculated values：535.23).Theoretical elemental content (%) C41H29N：C,91.93；H,5.46； N, 2.61 actual measurement constituent contents (%)：C,91.93；H,5.45；N,2.62.The above results confirm that it is target product to obtain product.
[embodiment 2] compound TM9 synthesis
Change bromo- 9, the 9- dimethyl fluorenes of 2- in embodiment 1 into bromo- 9, the 9- diphenylfluorenes of equimolar 2-, other steps It is identical with the synthesis of embodiment 1, obtain target product TM9.Mass spectrum m/z：659.27 (calculated values：659.26).Theoretical elemental Content (%) C51H33N：C,92.84；H,5.04；N, 2.12 actual measurement constituent contents (%)：C,92.84；H,5.04；N,2.12.On Stating result confirms that it is target product to obtain product.
[embodiment 3] compound TM17 synthesis
Change bromo- 9, the 9- dimethyl fluorenes of 2- in embodiment 1 into the equimolar 2- bromo- fluorenes of 9,9- spiral shells two, other steps are equal It is identical with the synthesis of embodiment 1, obtain target product TM17.Mass spectrum m/z：657.27 (calculated values：657.25).Theoretical elemental contains Measure (%) C51H31N：C,93.12；H,4.75；N, 2.13 actual measurement constituent contents (%)：C,93.13；H,4.74；N,2.13.It is above-mentioned As a result confirm that it is target product to obtain product.
[embodiment 4] compound TM19 synthesis
The synthesis of 5- bromine acenaphthylenes
Into 5- bromines acenaphthene (25.4g, 107.3mmol) and dehydration benzene 500mL, the chloro- dicyano-Isosorbide-5-Nitrae-benzoquinones of 2,3- bis- is added (DDQ) (29.2g, 128.7mmol), it is being heated to reflux lower stirring 6h.Added into reaction system DDQ (6.0g, 26.4mmol), stirring 4 hours is continued.After natural cooling, sediment is filtered out, is cleaned with chloroform.Merging filtrate, successively with 10% Sodium hydrate aqueous solution, water cleaning.After liquid separation, with anhydrous sodium sulfate drying organic phase, solvent is distilled off.It is dried under reduced pressure Residue, the solid as brown obtain 5- bromines acenaphthylene (13.0g, yield 51.6%).
The synthesis of bromo- 7,12- diphenyl benzo [k] fluoranthene of 3-
In the case where being heated to reflux, by 1,3- diphenyl isobenzofuran (14.9g, 55.2mmol), 5- bromines acenaphthylene (12.8g, The mixture stirring 16h of toluene 50mL 55.2mmol).After solvent is distilled off, acetic acid 1200mL is added, is heated to 80 DEG C. 48%HBr aqueous solution 150mL are added into the mixture, 1h is stirred at 80 DEG C.After being cooled to room temperature, sediment is filtered to obtain, is used Methanol cleans.By the yellow solid re crystallization from toluene of gained, crystal is filtered to obtain, bromo- 7, the 12- hexichol of 3- is obtained as yellow solid Base benzo [k] fluoranthene (19.8g, yield 74%)
The synthesis of intermediate A -2
By the 3- bromobenzenes in the synthesis of the intermediate A -1 of embodiment 1, simultaneously [k] fluoranthene changes the bromo- 7,12- hexichol of equimolar 3- into Base benzo [k] fluoranthene, other steps are identical with the synthesis of the intermediate A -1 of embodiment 1, obtain intermediate A -2.Mass spectrum m/z： 495.21 (calculated values：495.20).Theoretical elemental content (%) C38H25N：C,92.09；H,5.08；N, 2.83 actual measurement elements contain Measure (%)：C,92.09；H,5.09；N,2.82.The above results confirm that it is target product to obtain product.
Compound TM19 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 TM19.Mass spectrum m/z：809.30 (calculated values：809.31). Theoretical elemental content (%) C63H39N：C,93.42；H,4.85；N, 1.73 actual measurement constituent contents (%)：C,93.43；H,4.84； N,1.73.The above results confirm that it is target product to obtain product.
[embodiment 5] compound TM25 synthesis
The synthesis of intermediate A -3
Change the aniline in the synthesis of the intermediate A -1 of embodiment 1 into equimolar 4- aminobphenyls, other steps with reality It is identical to apply the synthesis of the intermediate A -1 of example 1, obtains intermediate A -3.Mass spectrum m/z：419.15 (calculated values：419.17).Theoretical elemental Content (%) C32H21N：C,91.62；H,5.05；N, 3.34 actual measurement constituent contents (%)：C,91.62；H,5.04；N,3.34.On Stating result confirms that it is target product to obtain product.
Compound TM25 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 TM25.Mass spectrum m/z：611.25 (calculated values：611.26). Theoretical elemental content (%) C47H33N：C,92.27；H,5.44；N, 2.29 actual measurement constituent contents (%)：C,92.28；H,5.44； N,2.28.The above results confirm that it is target product to obtain product.
[embodiment 6] compound TM67 synthesis
The synthesis of intermediate A -4
Change the aniline in the synthesis of the intermediate A -1 of embodiment 1 into equimolar 3- amino-N- phenyl carbazoles, other steps It is rapid identical with the synthesis of the intermediate A -1 of embodiment 1, obtain intermediate A -4.Mass spectrum m/z：508.20 (calculated values：508.19). Theoretical elemental content (%) C38H24N2：C,89.74；H,4.76；N, 5.51 actual measurement constituent contents (%)：C,89.73；H,4.76； N,5.51.The above results confirm that it is target product to obtain product.
Compound TM38 synthesis
Change the intermediate A -1 in the compound TM1 of embodiment 1 synthesis into equimolar intermediate A -4, other steps are equal It is identical with the compound TM1 of embodiment 1 synthesis, obtain target product TM38.Mass spectrum m/z：700.28 (calculated values：700.29). Theoretical elemental content (%) C53H36N2：C,90.83；H,5.18；N, 4.00 actual measurement constituent contents (%)：C,90.82；H,5.17； N,4.01.The above results confirm that it is target product to obtain product.
[embodiment 7] compound TM42 synthesis
Change bromo- 9, the 9- dimethyl fluorenes of 2- in embodiment 1 into the equimolar 4- bromo- fluorenes of 9,9- spiral shells two, other steps are equal It is identical with the synthesis of embodiment 1, obtain target product TM42.Mass spectrum m/z：535.24 (calculated values：535.23).Theoretical elemental contains Measure (%) C41H29N：C,91.93；H,5.46；N, 2.61 actual measurement constituent contents (%)：C,91.93；H,5.45；N,2.62.It is above-mentioned As a result confirm that it is target product to obtain product.
[embodiment 8] compound TM60 synthesis
Change the bromo- fluorenes of 9,9- spiral shells two of 2- in embodiment 4 into the equimolar 4- bromo- fluorenes of 9,9- spiral shells two, other steps with Embodiment 1 is identical, obtains target product TM60.Mass spectrum m/z：809.30 (calculated values：809.31).Theoretical elemental content (%) C63H39N：C,93.42；H,4.85；N, 1.73 actual measurement constituent contents (%)：C,93.43；H,4.84；N,1.73.The above results are demonstrate,proved The real product that obtains is target product.
[contrast Application Example]
By Corning (healthy and free from worry) 15 Ω of society/cm2 (1000) ito substrate successively in acetone, isopropanol, wash respectively in pure water Net 15 minutes, and expose 30 minutes under ultraviolet light, then handled 10 minutes with plasma.Then by the ito substrate after processing It is put into evaporated device.One layer of 30nm NPB is deposited first as hole transmission layer, followed by the evaporation of luminescent layer, mixing are deposited BH1 and 5% BD1,30nm Alq3 is then deposited as electron transfer layer, 0.5nm LiF are then deposited again, then evaporation 60nm metal Al.
[Application Example]
By Corning (healthy and free from worry) 15 Ω of society/cm2 (1000) ito substrate successively in acetone, isopropanol, wash respectively in pure water Net 15 minutes, and expose 30 minutes under ultraviolet light, then handled 10 minutes with plasma.Then by the ito substrate after processing It is put into evaporated device.The compound TM of one layer of 30nm embodiment B synthesis is deposited first as hole transmission layer, followed by it is luminous The evaporation of layer, mixing evaporation BH1 and 5% BD1, is then deposited 30nm Alq3 as electron transfer layer, is then deposited again 0.5nm LiF, 60nm metal Al is then deposited.
The electron luminescence characteristic of the organic luminescent device of above method manufacture represents in the following table：
Result above shows that a kind of aromatic amine analog derivative of class formation containing fluorenes of the invention is applied to organic illuminator In part, especially as hole mobile material, the advantages of showing high luminous efficiency, long lifespan, be organic hair of good performance Luminescent material.
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 (6)

1. the aromatic amine analog derivative of a kind of class formation containing fluorenes, it is characterised in that structural formula is as shown in formula I：
Wherein, in substituted or unsubstituted aryl of the Ar selected from C6~C50, C6~C50 substituted or unsubstituted heteroaryl It is a kind of；R1Selected from hydrogen atom, C1~C10 substituted or unsubstituted alkyl, C6~C50 substituted or unsubstituted aryl in It is a kind of；R2Substituted or unsubstituted alkyl selected from C1~C10, one kind in C6~C50 substituted or unsubstituted aryl.
2. the aromatic amine analog derivative of a kind of class formation containing fluorenes according to claim 1, it is characterised in that Ar is selected from C6 One kind in~C30 substituted or unsubstituted aryl, C6~C19 substituted or unsubstituted heteroaryl；R1Selected from hydrogen atom, One kind in C1~C6 substituted or unsubstituted alkyl, C6~C30 substituted or unsubstituted aryl；R2Selected from C1~C4's Substituted or unsubstituted alkyl, C6~C15 substituted or unsubstituted aryl in one kind.
3. the aromatic amine analog derivative of a kind of class formation containing fluorenes according to claim 1, it is characterised in that Ar is selected from benzene Base, naphthyl, anthryl, xenyl, terphenyl, pyrrole radicals, pyridine radicals, thienyl, furyl, indyl, quinolyl, isoquinolin Base, benzothienyl, benzofuranyl, dibenzofuran group, dibenzothiophenes base or carbazyl.
4. the aromatic amine analog derivative of a kind of class formation containing fluorenes according to claim 1, it is characterised in that described to contain fluorenes Any one of the aromatic amine analog derivative of class formation in structure shown in following TM1~TM65：
5. a kind of organic luminescent device, it is characterised in that the organic luminescent device includes anode, negative electrode and organic matter layer, institute State the aromatic amine analog derivative containing a kind of class formation containing fluorenes described in any one of Claims 1 to 4 in organic matter layer.
6. a kind of organic luminescent device according to claim 5, it is characterised in that described in any one of claims 1 to 3 A kind of aromatic amine analog derivative of class formation containing fluorenes is used as hole mobile material in an organic light emitting device.
CN201710627371.6A 2017-07-28 2017-07-28 The aromatic amine analog derivative and its organic luminescent device of a kind of class formation containing fluorenes Withdrawn CN107382749A (en)

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CN107629062A (en) * 2017-10-09 2018-01-26 长春海谱润斯科技有限公司 A kind of carbazole analog derivative and its organic luminescent device
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CN107698488A (en) * 2017-10-09 2018-02-16 长春海谱润斯科技有限公司 A kind of benzo carbazole analog derivative and its organic luminescent device
EP3502107A1 (en) * 2017-12-20 2019-06-26 Samsung Display Co., Ltd. 1-aminodibenzofuran-based compound and organic light-emitting device including the same
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Application publication date: 20171124