CN108727415A - compound and organic electroluminescence device - Google Patents

compound and organic electroluminescence device Download PDF

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Publication number
CN108727415A
CN108727415A CN201710248321.7A CN201710248321A CN108727415A CN 108727415 A CN108727415 A CN 108727415A CN 201710248321 A CN201710248321 A CN 201710248321A CN 108727415 A CN108727415 A CN 108727415A
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compound
base
substituted
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范洪涛
吕钟
任雪艳
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Beijing Eternal Material Technology Co Ltd
Guan Eternal Material Technology Co Ltd
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Beijing Eternal Material Technology Co Ltd
Guan Eternal Material Technology Co Ltd
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Abstract

The invention discloses a kind of organic electroluminescent compounds and include purposes of the compound in preparing organic electroluminescence device, the present invention also provides a kind of organic electroluminescence device, which includes the organic electroluminescent compounds.The compound of the present invention realizes good electron injection and transporting by introducing lactams condensed cyclic structure.

Description

Compound and organic electroluminescence device
Technical field
The present invention relates to a kind of noval chemical compound, the organic electroluminescence device for having used the compound is further related to, further , further relate to application of the compound in ORGANIC ELECTROLUMINESCENCE DISPLAYS and lighting technical field.
Background technology
Now with OLED technology in the continuous propulsion for illuminating and showing two big fields, people are for its core material Research focuses more on, and the organic electroluminescence device of an excellent in efficiency long lifespan is typically device architecture and various organic materials Material optimization collocation as a result, this functionalization material for just designing and developing various structures for chemists provides greatly machine It meets and challenges.Common functionalization organic material has：Hole-injecting material, hole mobile material, hole barrier materials, electronics Injection material, electron transport material, electron-blocking materials and light emitting host material and light-emitting guest (dyestuff) etc..In order to make The better luminescent device of standby performance, industry have been devoted to develop new electroluminescent organic material to further increase device Luminous efficiency and the service life.
By years of researches and development, electroluminescent organic material and device have had reached practical level, hole Transmission material, electron transport material, luminescent material, display device technology of preparing etc. have been achieved for considerable progress.Equally Ground, transmittability is stronger, the higher all types of electron transport materials of stability, is all had been reported that in previous article and patent. In general, electron transport material is all the compound of the nitrogen heterocyclic ring group with electron deficient, they have higher mostly Electron affinity, thus have it is stronger connect nucleophobic ability, but relative to hole mobile material, common electron-transport The electron mobility of material such as AlQ3(8-hydroxyquinoline aluminum) will be far below the hole mobility of hole mobile material, thus The recombination probability in hole and electronics caused by the one hand leading to the injection of carrier in OLED device and transmit unbalanced It reduces, to reduce the luminous efficiency of device, on the other hand the electron transport material with relatively low electron mobility can lead to device The operating voltage of part increases, unfavorable to the saving of the energy to influence power efficiency.
In current OLED screen body manufacturer, it widely is doped to the technological means in ET material layers using QLi, to realize The low-voltage and high efficiency of device, and it is improved the effect of device lifetime, the effect of QLi is essentially consisted in and can be noted in cathode Micro lithium metal is restored under the electronic action entered, to play the effect for carrying out n- doping to electron transport material, to So that the injection significant effect of electronics is promoted, on the other hand, lithium ion can pass through the coordination with N atoms in electron transport material Effect is played the role of improving ET material electronics mobilities, so that the device of QLi doping ET has low operating voltage With high luminous efficiency.
In conclusion in order to further meet the demand constantly promoted to the photoelectric properties of OLED device and mobile Electronic device needs constantly to develop novel, efficient OLED material for energy-efficient demand, has wherein exploitation is new The electron transport material tool of high mobility has very important significance.
Invention content
To solve the above problems, the present invention provides a kind of novel compound for organic electroluminescence device.The chemical combination Object realizes good electronic transmission performance by introducing novel lactams condensed cyclic structure.The compound of the present invention is by as follows Logical formula (I) indicates.
L1And L2It is independently selected from key, substituted or unsubstituted C6~C30Aryl (preferably substitution or unsubstituted C6- C12Aryl) or substituted or unsubstituted C2~C30Heteroaryl (preferably substitution or unsubstituted C4~C12Heteroaryl, it is described Heteroaryl preferably comprise 1 to 2 be selected from N, O or S hetero atoms)；
Ar can be selected from substituted or unsubstituted C6~C90Aryl (preferably substitution or unsubstituted C6-C24Aromatic hydrocarbons Base；Further preferably substitution or unsubstituted C6-C12Aryl), substituted or unsubstituted C2~C90Heteroaryl is (preferably Substitution or unsubstituted C4~C30Heteroaryl, the heteroaryl preferably comprise 1,2,3 or 4 and are independently selected from N, O or S Hetero atom；Further preferably substitution or unsubstituted C4~C12Heteroaryl), the aryl of Ar and heteroaryl can be condensed ring, Preferably C6~C90Substituted or non-substituted condensed-nuclei aromatics base or heteroaryl (preferably substitution or unsubstituted C6~C30It is thick Cyclophane alkyl or heteroaryl, the heteroaryl preferably comprise 1,2, the 3 or 4 miscellaneous original for being independently selected from N, O or S Son；Further preferably substitution or unsubstituted C6~C12Condensed-nuclei aromatics base or heteroaryl), C6~C90It is substituted or non-substituted Condensed-nuclei aromatics base or fused ring heteroaryl (preferably substitution or unsubstituted C6~C30Condensed-nuclei aromatics base or fused ring heteroaryl, institute The fused ring heteroaryl stated preferably comprises 1,2,3 or 4 hetero atom for being independently selected from N, O or S；Further preferably take Generation or unsubstituted C10~C24Condensed-nuclei aromatics base or fused ring heteroaryl).Ar can be C6-C30Substituted or unsubstituted ring Alkyl, C5-C30Substituted or unsubstituted Heterocyclylalkyl, C1~C12(preferably C1~C3) substituted or non-substituted straight chain One kind in alkyl or olefin group；
Above-mentioned Heterocyclylalkyl and/or heteroaryl include one or more selected from the miscellaneous of B, N, O, S, P, P (=O), Si and Se Atom；
R1、R2And R3It is independent to be selected from hydrogen, halogen, nitro, cyano, C1-C6Alkyl or C1-C6Alkoxy；
M, n and p is independently 0,1,2 or 3；When m is 2 or 3, R1It is identical or differ；When n is 2 or 3, R2Phase Together or differ；When p is 2 or 3, R3It is identical or differ.
Preferably, above-mentioned aryl includes but not limited to phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, indenes Base, fluorenyl and its derivative, fluoranthene base, triphenylene, pyrenyl, base,At least one of base and aphthacene base.It is more excellent Selection of land, the xenyl include 2- xenyls, 3- xenyls and 4- xenyls, and the terphenyl includes p- terphenyl- 4- bases, p- terphenyl -3- bases, p- terphenyl -2- bases, m- terphenyl -4- bases, m- terphenyl -3- bases and M- terphenyl -2- bases；The naphthalene is 1- naphthalenes and/or 2- naphthalenes；The anthryl includes 1- anthryls, 2- anthryls and 9- anthracenes At least one of base；The fluorenyl includes at least one of 1- fluorenyls, 2- fluorenyls, 3- fluorenyls, 4- fluorenyls and 9- fluorenyls； The fluorenyl derivative includes 9,9 '-dialkyl fluorenes, at least one of 9,9 '-spiral shell, two fluorenes and indenofluorene；The pyrenyl packet Include at least one of 1- pyrenyls, 2- pyrenyls and 4- pyrenyls；The aphthacene base include 1- aphthacenes base, 2- aphthacenes base and At least one of 9- aphthacene bases.
Preferably, the heteroaryl includes but not limited to furyl, thienyl, pyrrole radicals, pyrazinyl, quinoline, triazine Base, pyridyl group, benzofuranyl, benzothienyl, phentriazine, benzopyrazines, isobenzofuran-base, indyl, benzo quinoline Quinoline, dibenzofuran group, dibenzothiophene, dibenzopyrrole base, carbazyl and its derivative and benzo Dloxole At least one of alkenyl, wherein the carbazole radical derivative can include but is not limited to 9- phenyl carbazoles, 9- naphthyl carbazoles At least one of benzo carbazole, dibenzo-carbazole and indolocarbazole.
Ar can be C6-C30Substituted or unsubstituted naphthenic base, C5-C30Substituted or unsubstituted Heterocyclylalkyl, C1 ~C12(preferably C1~C3) substituted or non-substituted straight chained alkyl or olefin group in one kind.Preferably, described Naphthenic base is selected from cyclohexyl, cyclopenta, methylcyclohexyl, methylcyclopentyl, decahydronaphthalene naphthalene；The Heterocyclylalkyl is selected from Cyclohexyl that a carbon atom in its middle ring is replaced by N, O, S, cyclopenta, methylcyclohexyl, methylcyclopentyl or decahydronaphthalene Naphthalene；The straight chained alkyl or alkene is selected from methyl, ethyl, propyl, butyl, amyl, hexyl, vinyl, acrylic, fourth Alkenyl, butadienyl, pentenyl, pentadienyl, hexenyl, hexadienyl or hexatriene base.
In the present invention, Ca-CbExpression way represent the carbon atom number that the group has as a~b, unless specifically indicated, In general the carbon atom number does not include the carbon atom number of substituent group.
In the present invention, include the concept of the identical isotope of chemical property for the statement of chemical element, such as " hydrogen " Statement also includes chemical property identical " deuterium ", the concept of " tritium ".
Hetero atom in the present invention is often referred to selected from B, N, O, S, P, P (=O), Si and the atom in Se or atomic group.
In the present invention, when defined group is the group of substitution, it is preferred that on above-mentioned substituted group Substituent group includes but not limited to halogen, nitro, cyano, C1-C6Alkyl, C1-C6Alkoxy, C6-C12 aryl, C4- The heteroaryl etc. of C12, preferably C1~C5Alkyl, C1~C5Alkoxy, phenyl, naphthalene, pyridyl group, pyrrole radicals, it is more excellent Be selected as methyl, ethyl, isopropyl, phenyl, naphthalene, pyridyl group, the quantity of substituent group can be 1,2,3,4,5,6 and 6 with On.
In a preferred embodiment of the present invention, L1And L2The lactams condensed cyclic structure connected is identical；Into One step is preferred, L1And L2It is also identical with the connection site on the lactams condensed cyclic structure being connect.
According to the present invention, above-mentioned C6-C30Substituted or unsubstituted naphthenic base refers to, the quantity of carbon atom is preferably 3~ 10, more preferably 3-6.C5-C30Substituted or unsubstituted Heterocyclylalkyl refers to 5-30 ring skeleton atom and includes at least one A heteroatomic Heterocyclylalkyl selected from B, N, O, S, P, P (=O), Si and Se, it is preferable that the Heterocyclylalkyl refers to having 3-10 ring skeleton atom and include at least one Heterocyclylalkyl in O, S and N, the quantity of carbon atom is more preferably 3-5, the Heterocyclylalkyl are specifically including but not limited to tetrahydrofuran, pyrrolidines, thiophane.
In a preferred embodiment of the present invention, the compound of the present invention is by following general formula (I-1), general formula (I -2) Or general formula (I-3) indicates, the definition in relation to substituent group is consistent with logical formula (I).
In a preferred embodiment of the present invention, the L1And L2For identical group.
In a preferred embodiment of the present invention, for filming performance and processing performance aspect the considerations of, described The molecular weight of compound is between 500-1300, between preferably 600-1000.
In the present invention, the compound indicated by structural formula (1), (2), (3) can be selected from following compound：
In order to improve the electron injection and transmission performance of material, need selection that there is the group compared with the sub- affinity of forceful electric power, The group of common electron transport material includes the groups such as pyridine, quinoline, Phen, triazine, and the compound in the present invention is adopted With a kind of novel group with the very sub- affinity of forceful electric power：Iso-indoles and carbazole ketone structure (as follows), Wo Menfa The LUMO of existing iso-indoles and carbazole ketone parent compound is about -2.151eV, is markedly inferior to common drawing electron group for example The LUMO energy of pyridine (- 0.61eV), quinoline (- 1.38eV), Phen (- 1.41eV) and triphenyl triazine (- 1.80eV) Grade, shows iso-indoles and carbazole ketone groups have high electron affinity, is a kind of excellent drawing electron group, has such The compound of substituent group has good electron injection performance.Additionally, due to iso-indoles and carbazole ketone is with extraordinary flat altogether The conjugated structure in face so that the π-π between group can fully occur in the solid state for the compound molecule with such substituent group Interaction, to be conducive to transmission of the electronics between material molecule so that this kind of material has very high electron transfer Rate.This kind of material applies the operating voltage that device is advantageously reduced in OLED device, improves the luminous efficiency of device.
Compound in the present invention, on the one hand due to high electron affinity specific to precursor structure, thus with cathode material The work function of material is more nearly so that material easily can obtain electronics from cathode, have the sub- injection of forceful electric power；It is another This material of aspect has very high electron mobility.2 points comprehensive, material of the present invention is in the case of exclusive use, it will be able to The technique effect achieved by the common ET collocation QLi of industry is realized, to avoid coming using the QLi to water and environment sensitive On the one hand the ET materials for routine of arranging in pairs or groups reduce the use type of material, advantageously reduce material in screen scale of construction producing line in this way Expect cost, the evaporation source number of volume production equipment on the other hand can be reduced, to reduce the design and manufacture cost and technique of equipment Complexity has very big meaning.
The present invention also provides purposes of the above-mentioned organic electroluminescent compounds in preparing organic electroluminescence device. Organic electroluminescence device structure and the well known device of the present invention has no difference, generally comprise first electrode, second electrode and Be inserted between the first electrode and second electrode one layer or mostly at organic layer, which is characterized in that the organic layer includes upper State organic electroluminescent compounds.As the organic layer between first electrode and second electrode, usually there are electron injecting layer, electricity The organic layers such as sub- transport layer, luminescent layer, hole transmission layer, hole injection layer.The compound of the present invention may be used as but be not limited to Electron transport material or light emitting host material.
The present invention also provides purposes of the above-mentioned organic electroluminescent compounds in preparing organic electroluminescence device.
Wherein, the organic electroluminescent compounds may be used as but be not limited to electron transport material or light emitting host material Material.
The present invention also provides a kind of organic electroluminescence device, which includes first electrode, second electrode and insertion One layer between the first electrode and second electrode or mostly at organic layer, the organic layer includes above-mentioned organic electroluminescent Compound.
Specific implementation mode
With reference to following examples set forth the preparation methods of the representation compound of the present invention.Since the compounds of this invention has Have an identical skeleton, those skilled in the art are based on these preparation methods, can by known functional group's conversion method, readily Synthesize other the compound of the present invention.Hereinafter, also providing the preparation method and photism of the luminescent device comprising the compound Matter measures.
Various chemicals used in the present invention such as petroleum ether, ethyl acetate, n-hexane, toluene, tetrahydrofuran, two The bromo- 2- methyl naphthalenes of chloromethanes, benzindole ketone, 1-, adjacent bromo-iodobenzene, palladium, tricyclohexyl phosphine tetrafluoroborate, adjacent dibromo The iodo- 4- nitrobenzenes of the bromo- 2- of benzene, 1-, butyl lithium, 1- (2- bromophenyls) -2- methyl naphthalenes, N- bromo-succinimides, three (two Asias Benzylacetone) two palladiums, tetrakis triphenylphosphine palladium, Pd (dppf) Cl2, connection the bases such as pinacol borate and other halogenated aryl hydrocarbons Plinth industrial chemicals chemical products can be commercially available at home.
General formula reaction 1：
General formula reaction 2：
Synthesis implements 1：The synthesis of intermediate M1
Under nitrogen protection, 1,8- naphthalenes lactim (59.2mmol, 10g), adjacent bromo-iodobenzene are added in 500ml there-necked flasks (59.2mmol, 16.7g), sodium tert-butoxide (118.4mmol, 11.2g), Pd2(dba)3(0.59mmol, 0.54g), 10% 3 uncle Butyl phosphorus (2%, 15.5ml), is dissolved in 200ml toluene, 100 DEG C of reaction 3h, processing, 200ml washings, and organic phase crosses silica gel Column, eluent are concentrated under reduced pressure, are boiled and washed with 100ml ethyl alcohol, and 100ml petroleum ethers, which boil, to be washed, and intermediate M1 product 16.2g are filtered to obtain, production Rate 85%, molecular weight 323
Synthesize example 2：The synthesis of intermediate M2
Intermediate M1 (31mmol, 10g), palladium (1%, 0.07g), tricyclohexyl phosphine tetrafluoroborate (3%, It 0.34g) is mixed with (200 milliliters) of DMF, is heated to 130 degree and reacts 3 hours, after reaction, be cooled to room temperature, be added 400 Milliliter pure water, is extracted with ethyl acetate, and organic phase is washed with 300ml, and organic phase is concentrated under reduced pressure, and silicagel column excessively (is washed after mixing silica gel De- liquid：Petroleum ether: ethyl acetate=2: 1), compound intermediate M2 (6.1g, 80.1%) is obtained.
Synthesize example 3：The synthesis of intermediate M3
Under nitrogen protection, 1,8- naphthalenes lactim (59.2mmol, 10g), the bromo- 2- of 1- iodo- 4 are added in 500ml there-necked flasks Nitrobenzene (59.2mmol, 19.4g), sodium tert-butoxide (118.4mmol, 11.2g), Pd2(dba)3(0.59mmol, 0.54g), 10% tri-tert phosphorus (2%, 15.5ml), is dissolved in 200ml toluene, 100 DEG C of reaction 3h, processing, and 200ml washings have Machine mutually crosses silicagel column, and eluent is concentrated under reduced pressure, and solid boils with 100ml ethyl alcohol and washed, and 100ml petroleum ethers, which boil, to be washed, filter product obtains To the total 18.5g of intermediate M3, yield 85%, molecular weight 368
Synthesize example 4：The synthesis of intermediate M4
By intermediate M3 (36.8g, 100mmol), palladium (0.23g, 1.0mmol), tricyclohexyl phosphine tetrafluoroborate (700 milliliters) mixing of (1.11g, 3.0mmol) and DMF, are heated to 130 degree and react 3 hours, after reaction, be cooled to room Temperature is added 700 milliliters of pure water, is extracted with ethyl acetate, and organic phase is washed with 300ml, and silica gel is mixed in reduced pressure, crosses silicagel column (eluent：Petroleum ether: ethyl acetate=2: 1), compound intermediate M4 (23.73g, 82.4%) is obtained.
Synthesize example 5：The synthesis of intermediate M6
Intermediate M44.4g is dissolved in 200ml ethyl alcohol, and about 11.25g stannous chlorides are added, are heated to flowing back, and reacts 3h.Instead It answers liquid that sodium carbonate is added to be adjusted to neutrality, filters, filtrate is extracted with ethyl acetate.Filtrate concentrates, and obtains intermediate M5 about 3.2g.Intermediate M52.5g is dissolved in dilute hydrochloric acid, sodium nitrite in aqueous solution is added dropwise in ice bath, stirs half an hour.Reaction solution is added dropwise Hydrobromic acid.Reaction solution is heated to 50 degrees Celsius, is reacted three hours.Reaction finishes, and reaction solution is adjusted to neutrality with sodium carbonate, uses Dichloromethane extracts, and extract liquor concentration through column chromatography for separation, obtains the total 2.1g of intermediate M6.
Synthesize example 6：The synthesis of intermediate M7
By intermediate M2 (24.3g, 100mmol), NBS (17.8g, 100mmol) and (400 milliliters) mixing of DMF, room temperature Reaction 5 hours, is poured into after reaction in 800 milliliters of water, and precipitation solid is boiled with 300ml ethyl alcohol to be washed, and is boiled with 300ml petroleum ethers It washes, intermediate M7 (28.9g, 90.1%) is obtained by filtration.
Synthesize example 7：The synthesis of intermediate M8
By (250 milliliters) mixing of intermediate M2 (24.3g, 100mmol) and acetic acid, 90 degree are heated to, bromine is added dropwise (32g, 200mmol) reacts 2 hours under 90 degree, is down to room temperature after reaction.It pours into 500 milliliters of water, solid is precipitated It is boiled and is washed with 300ml ethyl alcohol, boiled and washed with 300ml petroleum ethers, intermediate M8 (20.2g, 63.0%) is obtained by filtration.
Synthesize example 8：The synthesis of intermediate M9
By (200 milliliters) mixing of intermediate M2 (24.3g, 100mmol) and acetic acid, 90 degree are heated to, bromine is added dropwise (64g, 400mol) reacts 2 hours under 90 degree, is down to room temperature after reaction.It pours into 400 milliliters of water, uses dichloromethane Extraction, and organic phase is washed with water, vacuum distillation concentration carries out post separation (eluent to obtained distillation residue：Dichloromethane Alkane/petroleum ether), obtain intermediate M9 (33.9g, 84.9%).
Synthesize example 9：The synthesis of intermediate M10
Under nitrogen protection, by intermediate M7 (32.1g, 100mmol) and duplex pinacol borate (25.4g, 100mmol), it is dissolved in 300ml tetrahydrofurans, adds potassium acetate (29.4g, 300mmol), Pd (dppf) Cl2 (3.66g, 5mmol) is heated to 60 DEG C, reacts 8 hours, be cooled to room temperature, and 500ml ethyl acetate is added, and crosses silicagel column, washes De- liquid is concentrated under reduced pressure, and solid is primary with 100ml petroleum ethers, obtains intermediate M10 product 28.0g, yield 75.8%
Synthesize example 10：The synthesis of intermediate M11
Under nitrogen protection, by intermediate M8 (32.1g, 100mmol) and duplex pinacol borate (25.4g, 100mmol), it is dissolved in 300ml tetrahydrofurans, adds potassium acetate (29.4g, 300mmol), Pd (dppf) Cl2 (3.66g, 5mmol) is heated to 60 DEG C, reacts 8 hours, be cooled to room temperature, and 500ml ethyl acetate is added, and crosses silicagel column, washes De- liquid is concentrated under reduced pressure, and solid is primary with 100ml petroleum ethers, obtains intermediate M11 product 28.9g yields 78.3%
Synthesize example 11：The synthesis of intermediate M12
Under nitrogen protection, by intermediate M6 (32.1g, 100mmol) and duplex pinacol borate (25.4g, 100mmol), it is dissolved in 300ml tetrahydrofurans, adds potassium acetate (29.4g, 300mmol), Pd (dppf) Cl2 (3.66g, 5mmol) is heated to 60 DEG C, reacts 8 hours, be cooled to room temperature, and 500ml ethyl acetate is added, and crosses silicagel column, washes De- liquid is concentrated under reduced pressure, and solid is primary with 100ml petroleum ethers, obtains intermediate M12 product 28.9g yields 78.3%
Synthesize example 12：The synthesis of compound C1
By intermediate M10 (36.9g, 100mmol), 4,4 '-'-dibromobiphenyls (15.6g, 50mmol), Pd (PPh3)4 (1.16g, 1.0mmol), potassium carbonate (41.4g, 300mmol), toluene (400mL) and EtOH (200mL) and distilled water (200mL) is mixed, and is then stirred to react under reflux 4 hours.After the completion of reaction, it is down to room temperature, is filtered, filter cake is used successively 300ml water and 300ml ethanol rinses, are then recrystallized with dimethylbenzene, and compound C1 (27g, 85.0%) is obtained after drying.
Synthesize example 13：The synthesis of compound C2
Using synthetic method identical with compound C1, difference is, 4,4 '-'-dibromobiphenyls are replaced into equivalent 4,4 '-two bromo- 1,1 '-dinaphthyl after the completion of reaction, obtains compound C2 27.6g, yield 75.0%.
Synthesize example 14：The synthesis of compound C3
Using synthetic method identical with compound C1, difference is, will 4,4 '-'-dibromobiphenyls be replaced into equivalent 9,10- dibromoanthracenes, after the completion of reaction, obtain compound C3 24.2g, yield 73.2%.
Synthesize example 15：The synthesis of compound C4
Using synthetic method identical with compound C1, difference is, will 4,4 '-'-dibromobiphenyls be replaced into equivalent 3,5- dibromo fluoranthene, after the completion of reaction, obtain compound C4 26.2g, yield 76.4%.
Synthesize example 16：The synthesis of compound C5
Using synthetic method identical with compound C1, difference is, will 4,4 '-'-dibromobiphenyls be replaced into equivalent 9,10- bis- (4- bromophenyls) anthracene, after the completion of reaction, obtain compound C5 33.4g, yield 82.1%.
Synthesize example 17：The synthesis of compound C6
Using synthetic method identical with compound C1, difference is, will 4,4 '-'-dibromobiphenyls be replaced into equivalent 3,6-, bis- bromo- 9,9- dimethyl fluorenes, after the completion of reaction, obtain compound C6 27.1g, yield 80.2%.
Synthesize example 18：The synthesis of compound C7
Using synthetic method identical with compound C1, difference is, will 4,4 '-'-dibromobiphenyls be replaced into equivalent 3,6-, bis- bromo- 9- phenyl carbazoles, after the completion of reaction, obtain compound C7 23.7g, yield 65.3%.
Synthesize example 19：The synthesis of compound C8
Using synthetic method identical with compound C1, difference is, will 4,4 '-'-dibromobiphenyls be replaced into equivalent 2,2 '-'-dibromobiphenyls, after the completion of reaction, obtain compound C8 21.1g, yield 66.4%.
Synthesize example 20：The synthesis of compound C9
Using synthetic method identical with compound C1, difference is, will 4,4 '-'-dibromobiphenyls be replaced into equivalent 2,2 '-dibromo this bithiophene, after the completion of reaction, obtain compound C9 28.9g, yield 77.3%.
Synthesize example 21：The synthesis of compound C10
Using synthetic method identical with compound C1, difference is, will 4,4 '-'-dibromobiphenyls be replaced into equivalent 2,7- dibromo dibenzofurans, after the completion of reaction, obtain compound C10 25.5g, yield 78.5%.
Synthesize example 22：The synthesis of compound C11
Using synthetic method identical with compound C1, difference is, will 4,4 '-'-dibromobiphenyls be replaced into equivalent 9,9 '-dibromo dianthranides, after the completion of reaction, obtain compound C11 32.0g, yield 76.5%.
Synthesize example 23：The synthesis of compound C12
Using synthetic method identical with compound C1, difference is, will 4,4 '-'-dibromobiphenyls be replaced into equivalent 2,7- dibromo fluorenes, after the completion of reaction, obtain compound C11 19.0g, yield 68.5%.
Synthesize example 24：The synthesis of compound C13
Using synthetic method identical with compound C1, difference is, will 4,4 '-'-dibromobiphenyls be replaced into equivalent 2,7- bis- bromo- 6,6,12,12- tetramethyl -6,12- diphenyl, two fluorenes after the completion of reaction, obtains compound C13 27.5g, Yield 69.3%.
Synthesize example 25：The synthesis of compound C14
Using synthetic method identical with compound C1, difference is, will 4,4 '-'-dibromobiphenyls be replaced into equivalent 3,3 '-dibromo spiral shell, two fluorenes, after the completion of reaction, obtain compound C14 22g, yield 76.4%.
Synthesize example 26：The synthesis of compound C15
Using synthetic method identical with compound C1, difference is, will 4,4 '-'-dibromobiphenyls be replaced into equivalent 1,6- dibromo pyrenes, after the completion of reaction, obtain compound C15 29.2g, yield 85.4%.
Synthesize example 27：The synthesis of compound C16
Using synthetic method identical with compound C1, difference is, will 4,4 '-'-dibromobiphenyls be replaced into equivalent 2,7- dibromos it is luxuriant and rich with fragrance, after the completion of reaction, obtain compound C16 26.5g, yield 80.3%.
Synthesize example 28：The synthesis of compound C17
Using synthetic method identical with compound C1, difference is, will 4,4 '-'-dibromobiphenyls be replaced into equivalent 1,3- bis- (5- bromopyridines base) benzene, after the completion of reaction, obtain compound C17 25.6g, yield 71.5%.
Synthesize example 29：The synthesis of compound C18
By intermediate M11 (36.9g, 100mmol), 2,11- dibromos triphenylene (19.3g, 50mmol), Pd (PPh3)4 (116g, 1.0mmol), potassium carbonate (41.4g, 300mmol), toluene (400mL) and EtOH (200mL) and distilled water (200mL) Mixing, is then stirred to react 4 hours under reflux.After the completion of reaction, be down to room temperature, filter, filter cake successively use 300ml water and 300ml ethanol rinses, are then recrystallized with dimethylbenzene, and compound C18 (30.2g, 85.0%) is obtained after drying.
Synthesize example 30：The synthesis of compound C19
Using synthetic method identical with compound C18, difference is, 2,11- dibromo triphenylenes are replaced into equivalent 4,4 "-two bromo- 1,1 ', 3,1 "-terphenyl after the completion of reaction, obtains compound C19 31.9g, yield 83.2%.
Synthesize example 31：The synthesis of compound C20
Using synthetic method identical with compound C18, difference is, 2,11- dibromo triphenylenes are replaced into equivalent 2,2 '-dibromo spiral shell, two fluorenes reaction after the completion of, obtain compound C20 32.1g, yield 80.3%.
Synthesize example 32：The synthesis of compound C21
Using synthetic method identical with compound C18, difference is, 2,11- dibromo triphenylenes are replaced into equivalent Two (4- bromophenyls) diphenyl silanes reaction after the completion of, obtain compound C21 30.9g, yield 75.5%.
Synthesize example 33：The synthesis of compound C22
Using synthetic method identical with compound C18, difference is, 2,11- dibromo triphenylenes are replaced into equivalent Isosorbide-5-Nitrae-dibromine naphthalene reaction after the completion of, obtain compound C22 23.2g, yield 76.0%
Synthesize example 34：The synthesis of compound C23
Using synthetic method identical with compound C18, difference is, 2,11- dibromo triphenylenes are replaced into equivalent 2,6- dibromoanthracenes reaction after the completion of, obtain compound C23 27.1g, yield 82.2%
Synthesize example 35：The synthesis of compound C24
Using synthetic method identical with compound C18, difference is, 2,11- dibromo triphenylenes are replaced into equivalent 9,9- bis- (4- bromophenyls) fluorenes reaction after the completion of, obtain compound C24 27.1g, yield 82.2%
Synthesize example 36：The synthesis of compound C25
Using synthetic method identical with compound C18, difference is, 2,11- dibromo triphenylenes are replaced into equivalent 3,6-, bis- bromo- 9,9- dibutyl fluorenes reaction after the completion of, obtain compound C25 29.9g, yield 78.6%
Synthesize example 37：The synthesis of compound C26
Using synthetic method identical with compound C18, difference is, 2,11- dibromo triphenylenes are replaced into equivalent The bromo- 10- of 9- (4- bromonaphthalenes base) anthracene reaction after the completion of, obtain compound C26 30.1g, yield 76.6%
Synthesize example 38：The synthesis of compound C27
Using synthetic method identical with compound C18, difference is, 2,11- dibromo triphenylenes are replaced into equivalent 3,10-, bis- bromine reactions after the completion of, obtain compound C27 25.2g, yield 68.5%
Synthesize example 39：The synthesis of compound C28
Using synthetic method identical with compound C18, difference is, 2,11- dibromo triphenylenes are replaced into equivalent 9,10- bis- (4- bromophenyls) anthracene reaction after the completion of, obtain compound C28 31.9g, yield 78.6%
Synthesize example 40：The synthesis of compound C29
Using synthetic method identical with compound C18, difference is, 2,11- dibromo triphenylenes are replaced into equivalent 3,5-, bis- bromo- 4- phenyl -1,2,4- triazoles reaction after the completion of, obtain compound C29 20.3g, yield 64.5%
Synthesize example 41：The synthesis of compound C30
Using synthetic method identical with compound C18, difference is, 2,11- dibromo triphenylenes are replaced into equivalent The luxuriant and rich with fragrance reactions of 9,10- bis- (4 '-bromophenyl) after the completion of, obtain compound C34 23.1g, yield 56.9%
Synthesize example 42：The synthesis of compound C31
Using synthetic method identical with compound C18, difference is, 2,11- dibromo triphenylenes are replaced into equivalent Bromo- 2,3,5, the 6- tetraphenyl benzene of Isosorbide-5-Nitrae-two reaction after the completion of, obtain compound C31 28.9g, yield 66.9%
Synthesize example 43：The synthesis of compound C32
Using synthetic method identical with compound C18, difference is, 2,11- dibromo triphenylenes are replaced into equivalent The bromo- phenyl tetrafluoride reaction of Isosorbide-5-Nitrae-two after the completion of, obtain compound C32 18.4g, yield 58.2%
Synthesize example 44：The synthesis of compound C33
Using synthetic method identical with compound C18, difference is, 2,11- dibromo triphenylenes are replaced into equivalent 6,6 '-two bromo- 3,3 '-second bipyridines reaction after the completion of, obtain compound C33 20.9g, yield 65.6%
Synthesize example 45：The synthesis of compound C34
Using synthetic method identical with compound C18, difference is, 2,11- dibromo triphenylenes are replaced into equivalent 3,5- bis- (4- bromophenyls) -4- phenyl -1,2,4- triazoles reaction after the completion of, obtain compound C40 21.7g, yield 55.6%
Synthesize example 46：The synthesis of compound C36
By intermediate M12 (36.9g, 100mmol), 1,5- dibromine naphthalenes (14.3g, 50mmol), Pd (PPh3)4(1.16g, 1.0mmol), potassium carbonate (41.4g, 300mmol), toluene (400mL) and EtOH (200mL) and distilled water (200mL) mixing, Then it is stirred to react under reflux 4 hours.After the completion of reaction, it is down to room temperature, is filtered, filter cake uses 300ml water and 300ml successively Then ethanol rinse is recrystallized with dimethylbenzene, compound C36 (19.9g, 65.0%) is obtained after drying.
Synthesize example 47：The synthesis of compound C37
Using synthetic method identical with compound C36, difference is, 1,5- dibromine naphthalenes are replaced into the 3 of equivalent, After the completion of the reaction of bis- bromo- 9- phenyl carbazoles of 6-, compound C37 20.7g, yield 57.1% are obtained
Synthesize example 48：The synthesis of compound C35
Using synthetic method identical with compound C36, difference is, 1,5- dibromine naphthalenes are replaced into the 2 of equivalent, After the completion of bis- bromo- Isosorbide-5-Nitraes of 5--diphenyl benzene reaction, compound C35 19.9g, yield 55.9% are obtained
Synthesize example 49：The synthesis of compound C38
Using synthetic method identical with compound C36, difference is, 1,5- dibromine naphthalenes are replaced into the 2 of equivalent, After the completion of the reaction of 2 '-'-dibromobiphenyls, compound C38 15.9g, yield 49.8% are obtained
Synthesize example 50：The synthesis of compound C39
Using synthetic method identical with compound C36, difference is, 1,5- dibromine naphthalenes are replaced into the 2 of equivalent, After the completion of the reaction of bis- bromo- bisbenzothiazoles of 7-, compound C39 21.8g, yield 65.3% are obtained
Synthesize example 51：The synthesis of compound C40
Using synthetic method identical with compound C36, difference is, 1,5- dibromine naphthalenes are replaced into the 2 of equivalent, After the completion of 7- bis- bromo- two (dibenzofurans) reactions, compound C40 24.9g, yield 67.2% are obtained
Synthesize example 52：The synthesis of compound C41
Using synthetic method identical with compound C36, difference is, 1,5- dibromine naphthalenes are replaced into the 9 of equivalent, After the completion of the reaction of 10- dibromo phenanthrene, compound C41 23.9g, yield 72.3% are obtained
Synthesize example 53：The synthesis of compound C42
Using synthetic method identical with compound C36, difference is, 1,5- dibromine naphthalenes are replaced into the 9 of equivalent, After the completion of the reaction of 9- bis- (4- bromophenyls) fluorenes, compound C42 28.1g, yield 70.1% are obtained
Synthesize example 54：The synthesis of compound C43
Using synthetic method identical with compound C36, difference is, 1,5- dibromine naphthalenes are replaced into the 3 of equivalent, 9- bis- bromo- 1 obtains compound C43 23.6g, yield 66.5% after the completion of the reaction of 2 benzophenanthrenes
Synthesize example 55：The synthesis of compound C44
Using synthetic method identical with compound C36, difference is, 1,5- dibromine naphthalenes are replaced into the 2 of equivalent, After the completion of the reaction of bis- bromo- 9,10- benzophenanthrenes of 7-, compound C44 24.0g, yield 67.4% are obtained
Synthesize example 56：The synthesis of compound C45
Using synthetic method identical with compound C36, difference is, 1,5- dibromine naphthalenes are replaced into the 1 of equivalent, After the completion of the reaction of 6- dibromo pyrenes, compound C45 21.6g, yield 63.2% are obtained
Synthesize example 57：The synthesis of compound C46
Using synthetic method identical with compound C36, difference is, 1,5- dibromine naphthalenes are replaced into the 1 of equivalent, After the completion of the reaction of 8- dibromo phenanthrene, compound C46 19.5g, yield 58.9% are obtained
Synthesize example 58：The synthesis of compound C47
Using synthetic method identical with compound C36, difference is, 1,5- dibromine naphthalenes are replaced into the 2 of equivalent, After the completion of the thick dinaphthyl reaction of 8- dibromos, compound C47 28.5g, yield 80.1% are obtained
Synthesize example 59：The synthesis of compound C48
Using synthetic method identical with compound C36, difference is, 1,5- dibromine naphthalenes are replaced into the 2 of equivalent, After the completion of the reaction of 11- dibromobenzene azoles phenanthrene, compound C48 25.7g, yield 72.3% are obtained
Synthesize example 60：The synthesis of compound C49
Using synthetic method identical with compound C36, difference is, 1,5- dibromine naphthalenes are replaced into the 3 of equivalent, After the completion of the reaction of 6- dibromo dibenzofurans, compound C49 21.4g, yield 65.9% are obtained
Synthesize example 61：The synthesis of compound C50
Using synthetic method identical with compound C36, difference is, 1,5- dibromine naphthalenes are replaced into the 5 of equivalent, After the completion of the reaction of 8- dibromobenzene azoles phenanthrene, compound C50 20.3g, yield 60.9% are obtained
Synthesize example 62：The synthesis of compound C51
Using synthetic method identical with compound C36, difference is, 1,5- dibromine naphthalenes are replaced into the 9 of equivalent, After the completion of the reaction of 10- dibromoanthracenes, compound C51 18g, yield 58.5% are obtained
Using mass spectral analysis and elemental analysis, intermediate M1 to intermediate M12 and compound C1 to C60 is characterized, Data are shown in Table 1.
1 synthetic example characterization of compound data of table
Device embodiment
OLED device evaluation and test is carried out using following device architecture：ITO/HAT/HIL/HTL/EML/ETL/LiF/Al is (above-mentioned Abbreviation correspond to respectively ito anode/hole injection layer/hole transmission layer/luminescent layer/electron transfer layer/electron injecting layer/LiF with The cathode of Al, the meaning of above-mentioned abbreviation is identical below), the following chemical structure formula shows each used material of functional layer in device (all material is purchased from lark prestige reagent, purity to the structural formula of material>99.9%)：
Device embodiments 1. use the compounds of this invention as electron transport material
The glass plate for being coated with ITO (150nm) transparency conducting layer is ultrasonically treated in commercial detergent, in deionization It is rinsed in water, in acetone: ultrasonic oil removing in alcohol mixed solvent (volume ratio 1: 1) is baked to complete removing under clean environment Low energy cation beam bombarded surface is used in combination with ultraviolet light and ozone clean in moisture content；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned Vacuum evaporation HAT on anode tunic forms the first hole injection layer that thickness is 10nm；It is true on the first hole injection layer Sky vapor deposition 2-TNATA [4,4 ', 4 "-three (N, N- (2- naphthalenes)-phenyl amino) triphenylamines], form second that thickness is 60nm Hole injection layer；The vacuum evaporation compound N PB on the second hole injection layer forms the hole transmission layer that thickness is 20nm, Evaporation rate is 0.1nm/s；
Electroluminescence layer is formed on above-mentioned hole transmission layer, concrete operations are：By the Zn as luminous layer main body (Bzp)2It is placed in the cell of vacuum phase deposition equipment, by (piq) as dopant2Ir (acac) [two-(1- phenyl Isoquinolyl) acetylacetone,2,4-pentanedione iridium (III)] it is placed in another room of vacuum phase deposition equipment, it is steamed simultaneously with different rates Send out two kinds of materials, (piq)2A concentration of the 4% of Ir (acac), vapor deposition total film thickness are 30nm；
Vacuum evaporation compound C1 forms the electron transfer layer that thick film is 20nm on luminescent layer, and evaporation rate is 0.1nm/s；
The LiF of vacuum evaporation 0.5nm makees as electron injecting layer and thickness for the Al layers of 150nm on the electron transport layer For the cathode of device.
2. material of the present invention of device embodiments is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, by compound C1 Replace with C3.
3. material of the present invention of device embodiments is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, by compound C1 Replace with C6.
4. material of the present invention of device embodiments is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, by compound C1 Replace with C14.
5. material of the present invention of device embodiments is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, by compound C1 Replace with C18.
6. material of the present invention of device embodiments is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, by compound C1 Replace with C20.
7. material of the present invention of device embodiments is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, by compound C1 Replace with C24.
8. material of the present invention of device embodiments is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, by compound C1 Replace with C28.
9. material of the present invention of device embodiments is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, by compound C1 Replace with C35.
10. material of the present invention of device embodiments is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, by compound Cl Replace with C36.
11. material of the present invention of device embodiments is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, by compound C1 Replace with C38.
12. material of the present invention of device embodiments is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, by compound C1 Replace with C41.
13. material of the present invention of device embodiments is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, by compound C1 Replace with C49.
14. material of the present invention of device embodiments is used as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, by compound C1 Replace with C51.
Comparative device embodiment 1. uses Bphen as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, compound C1 is replaced For Bphen.
Comparative device embodiment 2. uses LG201:QLi is as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, compound C1 is replaced For 1: 1 LG201 and QLi, the form that double source steams altogether is taken to realize.
Testing example 1
Under same brightness, use 2602 digital sourcemeter luminance meters of Keithley (photoelectric instrument factory of Beijing Normal University) Measure the driving voltage and electric current of the organic electroluminescence device being prepared in device embodiments 1-14 and comparative example 1 and 2 Efficiency the results are shown in Table 2.
Table 2
Device embodiments 1-14 and comparative example 1, the identical feelings of other materials in organic electroluminescence device structure Under condition, series compound of the present invention is instead of Bphen in comparative device embodiment 1 as electron transport material.Seriation of the present invention The lumo energy matching for closing object and electron injecting layer, luminescent layer material of main part is more preferable, while good electron mobility performance It is easier to electron-transport, can more efficiently realize and balance with hole transport, thus device work electricity can be effectively reduced Pressure improves current efficiency and improves the luminous efficiency of luminescent device under same device architecture.
Device embodiments 1-14 and comparative example 2, the identical feelings of other materials in organic electroluminescence device structure Under condition, series compound of the present invention replaces in comparative device embodiment 2, the electron transport material LG201 collocation being commercialized For QLi as electron transport material, voltage is almost the same even lower, and efficiency also has to be promoted by a small margin, but LG201 needs to use QLi more sensitive to water collocation use is compared, and the compounds of this invention, can be without QLi due to deeper LUMO energy levels In the case of, the effect that electronics is injected into luminescent layer from cathode is effectively realized, to reduce process complexity, simultaneously Its higher electron mobility also contributes to improving luminous efficiency and reduces operating voltage.The above result shows that of the invention is new Electron transport material of the type organic material as organic electroluminescence device is organic luminescence function material of good performance, has It hopes and promotes commercial applications.
The preferred embodiment of the present invention has been described above in detail, still, during present invention is not limited to the embodiments described above Detail can carry out a variety of simple variants to technical scheme of the present invention within the scope of the technical concept of the present invention, These simple variants all belong to the scope of protection of the present invention.
It is further to note that specific technical features described in the above specific embodiments, in not lance It in the case of shield, can be combined by any suitable means, in order to avoid unnecessary repetition, the present invention is to various Possible combination no longer separately illustrates.
In addition, various embodiments of the present invention can be combined randomly, as long as it is without prejudice to originally The thought of invention, it should also be regarded as the disclosure of the present invention.

Claims (8)

1. a kind of compound, at least two lactams condensed cyclic structure, the structure of compound is indicated by leading to formula (I) as follows,
L1And L2It is independent to be selected from singly-bound, substituted or unsubstituted C6~C30Aryl, substituted or unsubstituted C2~C30Heteroaryl Base；
Ar is selected from substituted or unsubstituted C6~C90Aryl, substituted or unsubstituted C2~C90Heteroaryl, C6-C30Substitution Or unsubstituted naphthenic base, C5-C30Substituted or unsubstituted Heterocyclylalkyl, C1~C12Substituted or non-substituted straight chained alkyl Or one kind in olefin group；
Hetero atom in the heteroaryl and Heterocyclylalkyl is one or more selected from the miscellaneous of B, N, O, S, P, P (=O), Si and Se Atom；
R1、R2And R3It is independent to be selected from hydrogen, halogen, nitro, cyano, C1-C6Alkyl or C1-C6Alkoxy；
M, n and p is independently 0,1,2 or 3；When m is 2 or 3, R1It is identical or differ；When n is 2 or 3, R2It is identical or It differs；When p is 2 or 3, R3It is identical or differ.
2. compound according to claim 1, the compound is by following general formula (I-1), general formula (I-2) or general formula (I- 3) it indicates
3. compound according to claim 1, L1And L2The lactams condensed cyclic structure connected is identical；Preferably, L1 And L2It is also identical with the connection site on the lactams condensed cyclic structure being connect.
4. compound according to claim 1 or 2, the aryl is independently selected from phenyl, xenyl, terphenyl Base, naphthalene, anthryl, phenanthryl, indenyl, fluorenyl and its derivative, fluoranthene base, triphenylene, pyrenyl, base,Base and aphthacene At least one of base；The heteroaryl it is independent selected from furyl, thienyl, pyrrole radicals, pyrazinyl, quinoline, triazine radical, Pyridyl group, benzofuranyl, benzothienyl, phentriazine, benzopyrazines, isobenzofuran-base, indyl, benzoquinoline, Dibenzofuran group, dibenzothiophene, dibenzopyrrole base, carbazyl and its derivative and benzodioxole group At least one of.
5. compound according to claim 1, the one kind of the compound in following compound：
6. a kind of organic electroluminescence device, which includes first electrode, second electrode and is inserted into the first electrode and the One layer between two electrodes or mostly at organic layer, which is characterized in that the organic layer includes any one of Claims 1 to 5 institute The compound stated.
7. organic electroluminescence device according to claim 6, the organic layer includes electron injecting layer, the electronics note It includes compound according to any one of claims 1 to 5 to enter layer.
8. organic electroluminescence device according to claim 6, the organic layer includes electron transfer layer, and the electronics passes Defeated layer includes compound according to any one of claims 1 to 5.
CN201710248321.7A 2017-04-14 2017-04-14 compound and organic electroluminescence device Pending CN108727415A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108727388A (en) * 2017-04-14 2018-11-02 北京鼎材科技有限公司 compound and organic electroluminescence device
KR20220165575A (en) * 2021-06-08 2022-12-15 중앙대학교 산학협력단 Isoindoloindolone derivatives and manufacturing method thereof

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CN103619986A (en) * 2011-06-03 2014-03-05 默克专利有限公司 Organic electroluminescence device
CN106188037A (en) * 2016-04-25 2016-12-07 中节能万润股份有限公司 A kind of compound based on 1,8-diaza-9-Fluorenone and application thereof
CN108727388A (en) * 2017-04-14 2018-11-02 北京鼎材科技有限公司 compound and organic electroluminescence device

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CN103619986A (en) * 2011-06-03 2014-03-05 默克专利有限公司 Organic electroluminescence device
CN106188037A (en) * 2016-04-25 2016-12-07 中节能万润股份有限公司 A kind of compound based on 1,8-diaza-9-Fluorenone and application thereof
CN108727388A (en) * 2017-04-14 2018-11-02 北京鼎材科技有限公司 compound and organic electroluminescence device

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108727388A (en) * 2017-04-14 2018-11-02 北京鼎材科技有限公司 compound and organic electroluminescence device
KR20220165575A (en) * 2021-06-08 2022-12-15 중앙대학교 산학협력단 Isoindoloindolone derivatives and manufacturing method thereof
KR102600522B1 (en) 2021-06-08 2023-11-10 중앙대학교 산학협력단 Isoindoloindolone derivatives and manufacturing method thereof

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