CN108178763A - A kind of organic electroluminescent compounds and the organic electroluminescence device using the compound - Google Patents
A kind of organic electroluminescent compounds and the organic electroluminescence device using the compound Download PDFInfo
- Publication number
- CN108178763A CN108178763A CN201711430621.3A CN201711430621A CN108178763A CN 108178763 A CN108178763 A CN 108178763A CN 201711430621 A CN201711430621 A CN 201711430621A CN 108178763 A CN108178763 A CN 108178763A
- Authority
- CN
- China
- Prior art keywords
- phenyl
- amido
- phenanthryl
- base
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 0 CCC=C(C*(CCC=C1)=C1N1C(C=C)=C)C1=C Chemical compound CCC=C(C*(CCC=C1)=C1N1C(C=C)=C)C1=C 0.000 description 4
- AGAMFZHIJWNZEG-UHFFFAOYSA-N BrC(C=C1)=CCC1I Chemical compound BrC(C=C1)=CCC1I AGAMFZHIJWNZEG-UHFFFAOYSA-N 0.000 description 1
- JXXOUTFTIHITKM-UHFFFAOYSA-N BrC(CC1)=CC=C1C(C=C1)=CCC1N(c(cc1)ccc1-c1cc(c2ccccc22)c3[n]2c(cccc2)c2c3c1)c(cc1)ccc1-c1cccc(c2ccc3)c1[o]c2c3-c(cc1)cc2c1-c1ccccc1C21c2ccccc2-c2c1cccc2 Chemical compound BrC(CC1)=CC=C1C(C=C1)=CCC1N(c(cc1)ccc1-c1cc(c2ccccc22)c3[n]2c(cccc2)c2c3c1)c(cc1)ccc1-c1cccc(c2ccc3)c1[o]c2c3-c(cc1)cc2c1-c1ccccc1C21c2ccccc2-c2c1cccc2 JXXOUTFTIHITKM-UHFFFAOYSA-N 0.000 description 1
- UCFSYHMCKWNKAH-UHFFFAOYSA-N CC1(C)OBOC1(C)C Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 description 1
- ZPFSISGFMDYHTL-UHFFFAOYSA-O C[C@H]1C(C)(C)[OH+]B([B+]2OC(C)(C)C(C)(C)O2)OC1(C)C Chemical compound C[C@H]1C(C)(C)[OH+]B([B+]2OC(C)(C)C(C)(C)O2)OC1(C)C ZPFSISGFMDYHTL-UHFFFAOYSA-O 0.000 description 1
- MMEGELSFOYDPQW-UHFFFAOYSA-N Cc(cc(cc1)N)c1Br Chemical compound Cc(cc(cc1)N)c1Br MMEGELSFOYDPQW-UHFFFAOYSA-N 0.000 description 1
- HCLMHNLHCYOECK-UHFFFAOYSA-N Cc(cc1)ccc1-c1cc(c2ccccc22)c3[n]2c(cccc2)c2c3c1 Chemical compound Cc(cc1)ccc1-c1cc(c2ccccc22)c3[n]2c(cccc2)c2c3c1 HCLMHNLHCYOECK-UHFFFAOYSA-N 0.000 description 1
- MWEKPLLMFXIZOC-UHFFFAOYSA-N OB(c(cc1)c(cc2)c3c1ccc1cccc2c31)O Chemical compound OB(c(cc1)c(cc2)c3c1ccc1cccc2c31)O MWEKPLLMFXIZOC-UHFFFAOYSA-N 0.000 description 1
- SZLNOBJKCVERBJ-UHFFFAOYSA-N c1ccc2[n](c(cccc3)c3c3ccc4)c3c4c2c1 Chemical compound c1ccc2[n](c(cccc3)c3c3ccc4)c3c4c2c1 SZLNOBJKCVERBJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
A kind of organic electroluminescence device the present invention provides organic electroluminescent compounds and using the compound.Organic electroluminescent compounds structure of the present invention is as follows：
Description
Technical field
The invention belongs to luminescent material technical fields, and in particular to a kind of organic electroluminescent compounds and use the chemical combination
The organic electroluminescence device of object.
Background technology
Organic electroluminescence device (Organic Light-emitting Devices, OLED) is to utilize following principle
Spontaneous luminescent device：When a field is applied, fluorescent material by anode injected holes and cathode injected electrons again
With reference to and shine.This selfluminous element has the characteristics such as voltage is low, brightness is high, visual angle is wide, response is fast, thermal adaptability is good,
And it is ultra-thin, the advantages that being produced on flexible panel, it is widely used in the fields such as mobile phone, tablet computer, TV, illumination.
Organic electroluminescence device has the structure similar to sandwich, including electrode material film layer and is clipped in difference
Electrode film layer or the organic functional material of self-recommendation, various different function materials are overlapped mutually according to purposes to be collectively constituted together
Organic electroluminescence device.As current device, when the two end electrodes to organic electroluminescence device apply voltage, and pass through electricity
Field action generates positive and negative charge in organic layer functional material film layer, the further compound generation light in luminescent layer of positive and negative charge,
This process is electroluminescent.
High performance research is proposed for organic electroluminescence device to include：The driving voltage of device is reduced, improves device
Luminous efficiency improves service life of device etc..In order to realize the continuous promotion of organic electroluminescence device performance, not only need
The innovation of the structure and manufacture craft of organic electroluminescence device, continuous research with greater need for organic electroluminescence photoelectric functional material and
The organic electroluminescence functional material of higher performance is formulated out in innovation.
For the actual demand of current organic electroluminescent industry, the development of electroluminescent organic material at present is also much
Not enough, the requirement of panel manufacturing enterprise is lagged behind, as material type enterprise, developing the organic functional material of higher performance seems outstanding
It is important.
In view of this, it is special to propose the present invention.
Invention content
The first object of the present invention is to provide a kind of organic electroluminescent compounds, organic electroluminescent chemical combination of the present invention
Object can be further used for the preparation of organic electroluminescence device, and realize the reduction of device drive voltage.
The second object of the present invention is to provide a kind of organic electroluminescence hair comprising organic electroluminescent compounds of the present invention
Optical device.
The third object of the present invention is to provide a kind of application of organic electroluminescence device of the present invention.
In order to realize the above-mentioned purpose of the present invention, spy uses following technical scheme：
A kind of organic electroluminescent compounds, the organic electroluminescent compounds structure are as follows：
Wherein, in formula (I), R1 is hydrogen, heavy hydrogen, the linear chain or branch chain type alkyl or hydrogen of C1~C20, phenyl, anilino-, two
Phenyl amido, 2- phenyl -3- aminopyridine bases, 3- amino bipyridyls, 2- phenyl-1-naphthylamine bases, 2- amido dinaphthyls, 2- benzene
Base -1- amido phenanthryl, two phenanthryl of 3- amidos, 2- phenyl -1- amido anthryls, two anthryl of 2- amidos, phenanthridinyl, xenyl, pyridine
Base, one kind in pyrimidine radicals, or triazine radical；
R2For hydrogen, heavy hydrogen, the linear chain or branch chain type alkyl or hydrogen of C1~C20, phenyl, pyridyl group, naphthalene, phenanthryl, anthryl,
One kind in phenanthridinyl, xenyl, pyridyl group, pyrimidine radicals or triazine radical；
R3For hydrogen, heavy hydrogen, the linear chain or branch chain type alkyl or hydrogen of C1~C20, phenyl, anilino-, diphenyl amido, 2- benzene
Base -3- aminopyridine bases, 3- amino bipyridyls, 2- phenyl-1-naphthylamine bases, 2- amido dinaphthyls, 2- phenyl -1- amidos are luxuriant and rich with fragrance
Base, two phenanthryl of 3- amidos, 2- phenyl -1- amido anthryls, two anthryl of 2- amidos, phenanthridinyl, xenyl, pyridyl group, pyrimidine radicals or
It is one kind of triazine radical；
L, m, n, o are respectively 0~4 integer.
Preferably, in organic electroluminescent compounds of the present invention, work as R1For phenyl, anilino-, diphenyl amido,
2- phenyl -3- aminopyridine bases, 3- amino bipyridyls, 2- phenyl-1-naphthylamine bases, 2- amido dinaphthyls, 2- phenyl -1- amidos
Phenanthryl, two phenanthryl of 3- amidos, 2- phenyl -1- amido anthryls, two anthryl of 2- amidos, phenanthridinyl, xenyl, pyridyl group, pyrimidine radicals,
Or during triazine radical, hydrogen more than one of them is by the linear or branched alkyl group of C1-C20, the cycloalkyl of C3-C24, C1-C20's
Alkoxy, halogen, CN, CF3, Si (CH3)3, naphthalene, anthryl, phenanthryl, dibenzofuran group, fluorenyl, carbazyl is Spirofluorene-based, with
And the heteroaryl of nuclear atom number 5-20 is substituted or non-substituted；
Preferably, in organic electroluminescent compounds of the present invention, work as R2For phenyl, pyridyl group, naphthalene, phenanthryl,
When anthryl, phenanthridinyl, xenyl, pyridyl group, pyrimidine radicals or triazine radical, the hydrogen more than one of them is by the straight chain of C1~C20
Or branched alkyl, the cycloalkyl of C3-C24, the alkoxy of C1-C20, halogen, CN, CF3, Si (CH3)3, naphthalene, anthryl, phenanthryl,
Benzofuranyl, dibenzofuran group, fluorenyl, carbazyl, the heteroaryl substitution or non-that Spirofluorene-based and nuclear atom number is 5-20
Substitution.
Preferably, in organic electroluminescent compounds of the present invention, work as R3For phenyl, anilino-, diphenyl amido,
2- phenyl -3- aminopyridine bases, 3- amino bipyridyls, 2- phenyl-1-naphthylamine bases, 2- amido dinaphthyls, 2- phenyl -1- amidos
Phenanthryl, two phenanthryl of 3- amidos, 2- phenyl -1- amido anthryls, two anthryl of 2- amidos, phenanthridinyl, xenyl, pyridyl group, pyrimidine radicals,
Or during triazine radical, hydrogen more than one of them is by the linear or branched alkyl group of C1-C20, the cycloalkyl of C3-C24, C1-C20's
Alkoxy, halogen, CN, CF3, Si (CH3)3, naphthalene, anthryl, phenanthryl, dibenzofuran group, fluorenyl, carbazyl is Spirofluorene-based, with
And the heteroaryl of nuclear atom number 5-20 is substituted or non-substituted.
Preferably, organic electroluminescent compounds of the present invention are any one of following compound：
Meanwhile the present invention also provides a kind of organic electroluminescence hairs comprising organic electroluminescent compounds of the present invention
Optical device.
Preferably, organic electroluminescence device of the present invention includes：Anode, hole injection layer, hole transmission layer, hair
The construction that photosphere, electron transfer layer, electron injecting layer and cathode are sequentially accumulated；
Wherein, electron-blocking layer is also optionally provided between anode and luminescent layer；It is also optional between cathode and luminescent layer
Be provided with hole blocking layer；Cathode surface is also optionally provided with coating.
Preferably, in organic electroluminescence device of the present invention, the hole transmission layer, electron-blocking layer, electronics
At least one layer in transport layer or hole group interlayer includes organic electroluminescent compounds of the present invention.
Further, present invention provides a kind of organic electroluminescences for including organic electroluminescence device of the present invention
Light-emitting display apparatus.
Likewise, the present invention also provides the organic electroluminescent compounds in organic electroluminescence device is prepared
Application；
And/or application of the organic electroluminescent compounds in organic electro-luminescence display device is prepared.
Compared with prior art, beneficial effects of the present invention are：
(1) organic electroluminescent compounds of the present invention can be used as hole transport layer material, electron-blocking layer material, electronics
Transport layer or hole blocking layer material and applied to the driving voltage that in organic electroluminescence device, can effectively reduce device,
Improve luminous efficiency, brightness, thermal stability, color purity and device lifetime.
(2) organic electroluminescence device of the present invention has driving voltage low, luminous efficiency is high, brightness is high, thermal stability is good,
The advantages that color purity height and long device lifetime.
Specific embodiment
Embodiment of the present invention is described in detail below in conjunction with embodiment, but those skilled in the art will
Understand, the following example is merely to illustrate the present invention, and is not construed as limiting the scope of the invention.It is not specified in embodiment specific
Condition person, the condition suggested according to normal condition or manufacturer carry out.Reagents or instruments used without specified manufacturer is
The conventional products that can be obtained by commercially available purchase.
There is a large effect for the performance of luminescent device in view of organic electroluminescent compounds, and existing Organic Electricity
Electro luminescent compounds can not simultaneously meet practical problem of the practical devices using needs, and the present invention provides a kind of novel Organic Electricities
Electro luminescent compounds, so as to meet the requirement of existing device.
Specifically, organic electroluminescent compounds structure provided by the present invention is as follows：
R1For hydrogen, heavy hydrogen, the linear chain or branch chain type alkyl of C1~C20, phenyl, anilino-, diphenyl amido, 2- phenyl-
3- aminopyridine bases, 3- amino bipyridyls, 2- phenyl-1-naphthylamine bases, 2- amido dinaphthyls, the non-base of 2- phenyl -1- amidos, 3-
Two phenanthryl of amido, 2- phenyl -1- amido anthryls, two anthryl of 2- amidos, phenanthridinyl, xenyl, pyridyl group, pyrimidine radicals or three
One kind of piperazine base；
Wherein, work as R1For phenyl, anilino-, diphenyl amido, 2- phenyl -3- aminopyridine bases, 3- amino bipyridyls,
2- phenyl-1-naphthylamine bases, 2- amido dinaphthyls, the non-base of 2- phenyl -1- amidos, two phenanthryl of 3- amidos, 2- phenyl -1- amido anthracenes
Base, two anthryl of 2- amidos, phenanthridinyl, xenyl, pyridyl group, when pyrimidine radicals or triazine radical, at least one hydrogen on the group
Atom can be by the linear or branched alkyl group of C1~C20, the cycloalkyl of C3-C24, the alkoxy of C1~C20, halogen, CN (cyanogen
Base), CF3(trifluoromethyl) and Si (CH3)3(trimethyl silicon substrate), naphthalene, anthryl, phenanthryl, dibenzofuran group, fluorenyl, carbazole
Base, Spirofluorene-based and nuclear atom number 5-20 heteroaryl substitution, so as to form the benzene with or without substituent structure
Base, anilino-, diphenyl amido, 2- phenyl -3- aminopyridine bases, 3- amino bipyridyls, 2- phenyl-1-naphthylamine bases, 2- amine
Base dinaphthyl, the non-base of 2- phenyl -1- amidos, two phenanthryl of 3- amidos, 2- phenyl -1- amido anthryls, two anthryl of 2- amidos, phenanthridines
Base, xenyl, pyridyl group, pyrimidine radicals, or triazine radical；
R2For hydrogen, heavy hydrogen, the linear chain or branch chain type alkyl of C1~C20, phenyl, pyridyl group, naphthalene, phenanthryl, anthryl, phenanthridines
Base, xenyl, pyridyl group, pyrimidine radicals or triazine radical；
Wherein, work as R2For phenyl, pyridyl group, naphthalene, phenanthryl, anthryl, phenanthridinyl, xenyl, pyridyl group, pyrimidine radicals or
During person's triazine radical, at least one hydrogen atom on the group can be by by the linear or branched alkyl group of C1~C20, the ring of C3-C24
Alkyl, the alkoxy of C1-C20, halogen, CN (cyano), CF3(trifluoromethyl), Si (CH3)3(trimethyl silicon substrate), naphthalene, anthracene
Base, phenanthryl, benzofuranyl, dibenzofuran group, fluorenyl, carbazyl, Spirofluorene-based and nuclear atom number are the heteroaryl of 5-20
It is substituted or non-substituted, so as to form the phenyl with or without substituent structure, pyridyl group, naphthalene, phenanthryl, anthryl, phenanthrene
Piperidinyl, xenyl, pyridyl group, pyrimidine radicals or triazine radical；
R3For hydrogen, heavy hydrogen, the linear chain or branch chain type alkyl of C1~C20, phenyl, anilino-, diphenyl amido, 2- phenyl-
3- aminopyridine bases, 3- amino bipyridyls, 2- phenyl-1-naphthylamine bases, 2- amido dinaphthyls, the non-base of 2- phenyl -1- amidos, 3-
Two phenanthryl of amido, 2- phenyl -1- amido anthryls, two anthryl of 2- amidos, phenanthridinyl, xenyl, yl pyridines base, pyrimidine radicals or
One kind of triazine radical；
Wherein, work as R3For phenyl, anilino-, diphenyl amido, 2- phenyl -3- aminopyridine bases, 3- amino bipyridyls,
2- phenyl-1-naphthylamine bases, 2- amido dinaphthyls, the non-base of 2- phenyl -1- amidos, two phenanthryl of 3- amidos, 2- phenyl -1- amido anthracenes
Base, two anthryl of 2- amidos, phenanthridinyl, xenyl, pyridyl group, when pyrimidine radicals or triazine radical, at least one hydrogen on the group
Atom can be by the linear or branched alkyl group of C1-C20, the cycloalkyl of C3-C24, the alkoxy of C1-C20, halogen, CN (cyano),
CF3(trifluoromethyl) and Si (CH3)3(trimethyl silicon substrate), naphthalene, anthryl, phenanthryl, dibenzofuran group, fluorenyl, carbazyl, spiral shell
The heteroaryl of fluorenyl and nuclear atom number 5-20 replace, so as to form the phenyl with or without substituent structure, aniline
Base, diphenyl amido, 2- phenyl -3- aminopyridine bases, 3- amino bipyridyls, 2- phenyl-1-naphthylamine bases, 2- amido dinaphthyls
Base, the non-base of 2- phenyl -1- amidos, two phenanthryl of 3- amidos, 2- phenyl -1- amido anthryls, two anthryl of 2- amidos, phenanthridinyl, biphenyl
Base, pyridyl group, pyrimidine radicals, or triazine radical；
L, m, n, o are independently respectively 0,1,2,3 or 4.
The synthesis of 1 compound 27 of embodiment
(1) synthesis of intermediate -1
[reaction equation 1]
In the three-necked flask of dry 2L, 24.4g (100mmol, 1.0eq.) 4- phenyl dibenzofurans is put into, is used
The tetrahydrofuran dissolving of 300ml dryings, leads to nitrogen, is down to -10 DEG C, the LDA of 44ml2.5M (110mmol, 1.1eq.) is added dropwise, treats
Completion of dropwise addition continues to stir 1 hour at such a temperature, 30.1g (150mmol, 1.5eq.) iodine is added portionwise, removes cooling ring
Border, the reaction was continued overnight, and to the end of reaction, the HCl solution of 4M is added dropwise, stirs 1 hour, stands, layering, upper organic phase washing
3 times, lower floor's organic phase is extracted with dichloromethane, is washed 3 times, merges organic phase, dry, and rotation is obtained except solvent, chromatographic column purification
33.7g intermediate -1, yield 91%.
(2) synthesis of intermediate -2
[reaction equation 2]
By 34.2g (200mmol, 1.0eq.) para-bromoaniline and 44.9g (220mmol, 1.1eq.) 5- phenyl -2- thiophene phenyls
Boric acid is added in the three-necked flask of 3L, is added in 1600ml toluene and the dissolving of 160ml ethyl alcohol, is led to nitrogen 15 minutes, adds
300ml 2M contain 82.9g (600mmol, 3.0eq.) K2CO3Aqueous solution, be eventually adding 4.6gPd (PPh3)4(2mol%).
110 DEG C are warming up to, reaction terminates overnight.Adding activated carbon adsorption, filter, rotation is dry except solvent, with toluene and ethyl alcohol recrystallization,
Obtain 39.2g intermediate -2, yield 78%.
(3) synthesis of intermediate -3
[reaction equation 3]
33.7g (91.0mmol, 1.0eq.) intermediates -1 and 27.5g are added in dry 3L three-necked flasks
(109.2mmol, 1.2eq.) intermediate -2 add dry and degasification 1200ml toluene and make solvent, lead to nitrogen 15 minutes.
Add 17.5g (182mmol, 2.0eq.) sodium tert-butoxide, 1.7g (2%mol) catalyst Pd2(dba)3With 7.4ml (4%mol)
P(t-bu)3Toluene solution (m/v, 10%).90 DEG C are warming up to, is reacted 2 hours.To the end of reaction, it is cooled to room temperature, adds work
Property charcoal absorption, filter, rotation with toluene and ethyl alcohol recrystallization, obtains 37.3g intermediate -3, yield 83% except solvent.
(4) synthesis of intermediate -4
[reaction equation 4]
37.3g (75.6mmol, 1.0eq.) intermediates -3 and 29.8g are added in dry 3L three-necked flasks
The bromo- 4- iodine biphenyl of (83.2mmol, 1.1eq.) 4- adds dry and degasification 1400ml toluene and makees solvent, leads to nitrogen 15
Minute.Add 10.9g (113.4mmol, 1.5eq.) sodium tert-butoxide, 1.4g (2%mol) catalyst Pd2(dba)3And 6.1ml
(4%mol) P (t-bu)3Toluene solution (m/v, 10%).90 DEG C are warming up to, is reacted 1.5 hours.To the end of reaction, it is cooled to
Room temperature adds activated carbon adsorption, filters, and rotation with toluene and ethyl alcohol recrystallization, obtains 37.8g intermediate -4, yield is except solvent
69%.
(5) synthesis of intermediate -5
[reaction equation 5]
Added in dry 3L three-necked flasks 32g (100mmol, 1.0eq.) 2- bromo indoles simultaneously [3,2,1-JK] carbazole and
27.9g (110mmol, 1.1eq.) connection boric acid pinacol ester adds dry and degasification 1600ml Isosorbide-5-Nitraes-dioxane and makees
Solvent, leads to nitrogen 15 minutes, adds in 0.7g catalyst Pd (dppf)2Cl2(3%mol) and 19.6g (200mmol, 2.0eq.) second
Sour potassium.100 DEG C are warming up to, reaction 5 hours overnight.It to the end of reaction, is cooled to room temperature, adds activated carbon, cross short column of silica gel, be spin-dried for
Filtrate with toluene and ethyl alcohol recrystallization, obtains 31.6g intermediate -5, yield 86%.
(6) synthesis of intermediate -6
[reaction equation 6]
By 14.8g (86mmol, 1.0eq.) para-bromoaniline and 31.6g (86mmol, 1.0eq.) intermediate -5, it is added to 2L
Three-necked flask in, add in 900ml toluene and the dissolving of 90ml ethyl alcohol, lead to nitrogen 15 minutes, add 129ml 2M and contain 82.9g
(258mmol,3.0eq.)K2CO3Aqueous solution, be eventually adding 2.0gPd (PPh3)4(2mol%).100 DEG C are warming up to, was reacted
Night terminates.Adding activated carbon adsorption, filter, rotation, with toluene and ethyl alcohol recrystallization, obtains 23.4g intermediate -6 except solvent, drying,
Yield is 82%.
(7) synthesis of intermediate -7
[reaction equation 7]
23.4g (70.5mmol, 1.1eq.) intermediates -6 and 20.7g are added in dry 3L three-necked flasks
(64.1mmol, 1.0eq.) 4- (4- bromophenyls)-dibenzofurans adds dry and degasification 900ml toluene and makees solvent,
Logical nitrogen 15 minutes.Add 12.3g (128.2mmol, 2.0eq.) sodium tert-butoxide, 1.2g (2%mol) catalyst Pd2(dba)3
With 5.2ml (4%mol) P (t-bu)3Toluene solution (m/v, 10%).90 DEG C are warming up to, is reacted 2 hours.To the end of reaction,
It is cooled to room temperature, adds activated carbon adsorption, filter, rotation, with toluene and ethyl alcohol recrystallization, obtains 28g intermediate -7, yield except solvent
It is 76%.
(8) synthesis of compound 27
[reaction equation 8]
Added in dry 3L three-necked flasks 28g (48.7mmol, 1.0eq.) intermediates -7 and 35.3g (48.7mmol,
1.0eq.) intermediate -4 add dry and degasification 1400ml toluene and make solvent, lead to nitrogen 15 minutes.Add 14g
(146.1mmol, 3.0eq.) sodium tert-butoxide, 0.9g (2%mol) catalyst Pd2(dba)3With 3.9ml (4%mol) P (t-bu)3
Toluene solution (m/v, 10%).90 DEG C are warming up to, is reacted 2 hours.To the end of reaction, it is cooled to room temperature, adds activated carbon adsorption,
It filters, rotation, with toluene and ethyl alcohol recrystallization, obtains 40.4g compounds 27, yield 68% except solvent.
Product atlas analysis data：
1H NMR(DMSO,300Hz):δ (ppm)=8.26-8.11 (d, 2H), 8.05-7.94 (m, 5H), 7.91-7.86
(s,1H),7.84-7.78(m,2H),7.75-7.11(m,42H),7.03-6.88(m,3H)；
MS(FAB):1213(M+)。
The synthesis of 2 compound 59 of embodiment
(1) synthesis of intermediate -8
[reaction equation 9]
By 24.7g (100mmol, 1.0eq.) 4- bromines dibenzofurans and 27.1g (110mmol, 1.1eq.) 1- pyrene boric acid,
It is added in the three-necked flask of 2L, adds in 1000ml toluene and the dissolving of 100ml ethyl alcohol, lead to nitrogen 15 minutes, add 150ml
2M contains 41.5g (300mmol, 3.0eq.) K2CO3Aqueous solution, be eventually adding 2.3gPd (PPh3)4(2mol%).It is warming up to
110 DEG C, reaction terminates overnight.Add activated carbon adsorption, filter, rotation, with toluene and ethyl alcohol recrystallization, is obtained except solvent, drying
32.8g intermediate -8, yield 89%.
(2) synthesis of intermediate -9
[reaction equation 10]
In the three-necked flask of dry 2L, 32.8g (89mmol, 1.0eq.) intermediate -8 are put into, with 350ml dryings
Tetrahydrofuran dissolves, and leads to nitrogen, is down to -10 DEG C, and the LDA of 39.2ml 2.5M (97.9mmol, 1.1eq.) is added dropwise, and waits that knot is added dropwise
Beam continues to stir 1 hour at such a temperature, 33.9g (133.5mmol, 1.5eq.) iodine is added portionwise, removes cooler environment, after
Continuous reaction overnight, to the end of reaction, is added dropwise the HCl solution of 4M, stirs 1 hour, stand, layering, upper organic phase is washed with water 3
Secondary, lower floor's organic phase is extracted with dichloromethane, is washed 3 times, merges organic phase, and dry, rotation is purified with chromatographic column, obtained except solvent
To 38.7g intermediate -9, yield 88%.
(3) synthesis of intermediate -10
[reaction equation 11]
38.7g (78.3mmol, 1.0eq.) intermediates -9 and 21.9g are added in dry 3L three-necked flasks
(86.2mmol, 1.1eq.) connection boric acid pinacol ester adds dry and degasification 1200ml1, and 4- dioxane makees solvent,
Logical nitrogen 15 minutes, adds in 1.3g catalyst Pd (dppf)2Cl2(2%mol) and 15.4g (156.6mmol, 2.0eq.) acetic acid
Potassium.100 DEG C are warming up to, reaction 5 hours overnight.It to the end of reaction, is cooled to room temperature, adds activated carbon, cross short column of silica gel, be spin-dried for filtering
Liquid with toluene and ethyl alcohol recrystallization, obtains 31.4g intermediate -10, yield 81%.
(4) synthesis of intermediate -11
[reaction equation 12]
By 31.4g (63.4mmol, 1.0eq.) intermediates -10 and 19.7g (69.8mmol, 1.1eq.) to bromo-iodobenzene, add
Enter into the three-necked flask of 2L, add in 1000ml toluene and the dissolving of 100ml ethyl alcohol, lead to nitrogen 15 minutes, add 95.1ml 2M
Aqueous solution containing 26.3g (190.2mmol, 3.0eq.) K2CO3 is eventually adding 1.5gPd (PPh3) 4 (2mol%).It is warming up to
110 DEG C, reaction terminates overnight.Add activated carbon adsorption, filter, rotation, with toluene and ethyl alcohol recrystallization, is obtained except solvent, drying
25.6g intermediate -11, yield 77%.
(5) synthesis of intermediate -12
[reaction equation 13]
Added in dry 3L three-necked flasks 32g (100mmol, 1.0eq.) 2- bromo indoles simultaneously [3,2,1-JK] carbazole and
27.9g (110mmol, 1.1eq.) connection boric acid pinacol ester, adds dry and degasification 1600ml1, and 4- dioxane is made
Solvent, leads to nitrogen 15 minutes, adds in 0.7g catalyst Pd (dppf)2Cl2(3%mol) and 19.6g (200mmol, 2.0eq.) second
Sour potassium.100 DEG C are warming up to, reaction 5 hours overnight.It to the end of reaction, is cooled to room temperature, adds activated carbon, cross short column of silica gel, be spin-dried for
Filtrate with toluene and ethyl alcohol recrystallization, obtains 31.6g intermediate -12, yield 86%.
(6) synthesis of intermediate -13
[reaction equation 14]
By 31.6g (86mmol, 1.0eq.) intermediates -12 and the bromo- 4 '-amino connection of 23.5g (94.6mmol, 1.1eq.) 4-
Benzene is added in the three-necked flask of 3L, is added in 1100ml toluene and the dissolving of 110ml ethyl alcohol, is led to nitrogen 15 minutes, adds
129ml 2M contain 35.7g (258mmol, 3.0eq.) K2CO3Aqueous solution, be eventually adding 2.0gPd (PPh3)4(2mol%).
110 DEG C are warming up to, reaction terminates overnight.Adding activated carbon adsorption, filter, rotation is dry except solvent, with toluene and ethyl alcohol recrystallization,
Obtain 29.2g intermediate -13, yield 83%.
(7) synthesis of intermediate -14
[reaction equation 15]
22g (53.8mmol, 1.1eq.) intermediates -13 and 25.6g are added in dry 3L three-necked flasks
(48.9mmol, 1.0eq.) intermediate -11 add dry and degasification 900ml toluene and make solvent, lead to nitrogen 15 minutes.
Add 9.4g (97.8mmol, 2.0eq.) sodium tert-butoxide, 0.9g (2%mol) catalyst Pd2(dba)3With 4.0ml (4%mol)
P(t-bu)3Toluene solution (m/v, 10%).90 DEG C are warming up to, is reacted 2 hours.To the end of reaction, it is cooled to room temperature, adds work
Property charcoal absorption, filter, rotation with toluene and ethyl alcohol recrystallization, obtains 29.5g intermediate -14, yield 71% except solvent.
(8) synthesis of intermediate -15
[reaction equation 16]
29.5g (34.7mmol, 1.0eq.) intermediates -14 and 13.7g are added in dry 3L three-necked flasks
The bromo- 4- iodine biphenyl of (38.2mmol, 1.1eq.) 4- adds dry and degasification 900ml toluene and makees solvent, and logical nitrogen 15 divides
Clock.Add 6.7g (69.4mmol, 2.0eq.) sodium tert-butoxide, 0.6g (2%mol) catalyst Pd2(dba)3With 2.8ml (4%
mol)P(t-bu)3Toluene solution (m/v, 10%).90 DEG C are warming up to, is reacted 2 hours.To the end of reaction, it is cooled to room temperature,
Add activated carbon adsorption, filter, rotation, with toluene and ethyl alcohol recrystallization, obtains 30.8g intermediate -15, yield 82% except solvent.
(9) synthesis of intermediate -16
[reaction equation 17]
By 17.2g (100mmol, 1.0eq.) para-bromoaniline and 22.4g (110mmol, 1.1eq.) 5- phenyl -2- thiophene phenyls
Boric acid is added in the three-necked flask of 2L, is added in 800ml toluene and the dissolving of 80ml ethyl alcohol, is led to nitrogen 15 minutes, adds
150ml 2M contain 41.5g (300mmol, 3.0eq.) K2CO3Aqueous solution, be eventually adding 2.3gPd (PPh3)4(2mol%).
110 DEG C are warming up to, reaction terminates overnight.Adding activated carbon adsorption, filter, rotation is dry except solvent, with toluene and ethyl alcohol recrystallization,
Obtain 21.9g intermediate -16, yield 87%.
(10) synthesis of intermediate -17
[reaction equation 18]
30.8g (28.5mmol, 1.0eq.) intermediates -15 and 7.9g are added in dry 3L three-necked flasks
(31.3mmol, 1.1eq.) intermediate -16 add dry and degasification 800ml toluene and make solvent, lead to nitrogen 15 minutes.
Add 5.5g (57mmol, 2.0eq.) sodium tert-butoxide, 0.5g (2%mol) catalyst Pd2(dba)3With 2.3ml (4%mol) P
(t-bu)3Toluene solution (m/v, 10%).90 DEG C are warming up to, is reacted 2 hours.To the end of reaction, it is cooled to room temperature, adds activity
Charcoal adsorbs, and filters, and rotation, with toluene and ethyl alcohol recrystallization, obtains 27.5g intermediate -17, yield 77% except solvent.
(11) synthesis of intermediate -18
[reaction equation 19]
In the three-necked flask of dry 2L, 24.7g (100mmol, 1.0eq.) 4- bromine dibenzofurans is put into, is used
The tetrahydrofuran dissolving of 300ml dryings, leads to nitrogen, is down to -10 DEG C, the LDA of 44ml2.5M (110mmol, 1.1eq.) is added dropwise, treats
Completion of dropwise addition continues to stir 1 hour at such a temperature, 30.1g (150mmol, 1.5eq.) iodine is added portionwise, removes cooling ring
Border, the reaction was continued overnight, and to the end of reaction, the HCl solution of 4M is added dropwise, stirs 1 hour, stands, layering, upper organic phase water
It washes 3 times, lower floor's organic phase is extracted with dichloromethane, is washed 3 times, merges organic phase, and dry, rotation removes solvent, is purified with chromatographic column,
Obtain 31g intermediate -18, yield 83%.
(12) synthesis of intermediate -19
[reaction equation 20]
By 13.0g (75.5mmol, 1.0eq.) 1- naphthalene boronic acids and 31g (83mmol, 1.1eq.) intermediate -18, it is added to
In the three-necked flask of 2L, 900ml toluene and the dissolving of 90ml ethyl alcohol are added in, leads to nitrogen 15 minutes, 113.2ml 2M is added and contains
31.3g(226.5mmol,3.0eq.)K2CO3Aqueous solution, be eventually adding 1.7gPd (PPh3)4(2mol%).It is warming up to 110
DEG C, reaction terminates overnight.Add activated carbon adsorption, filter, rotation, with toluene and ethyl alcohol recrystallization, obtains 22.5g except solvent, drying
Intermediate -19, yield 80%.
(13) synthesis of compound 59
[reaction equation 21]
Added in dry 3L three-necked flasks 27.5g (22mmol, 1.0eq.) intermediates -17 and 8.2g (22mmol,
1.0eq.) intermediate -19 add dry and degasification 700ml toluene and make solvent, lead to nitrogen 15 minutes.Add 4.2g
(44mmol, 2.0eq.) sodium tert-butoxide, 0.4g (2%mol) catalyst Pd2(dba)3With 1.8ml (4%mol) P (t-bu)3First
Benzole soln (m/v, 10%).90 DEG C are warming up to, is reacted 2 hours.It to the end of reaction, is cooled to room temperature, adds activated carbon adsorption, take out
Filter, rotation, with toluene and ethyl alcohol recrystallization, obtain 22.8g compounds 59, yield 67% except solvent.
Product spectrum data is analyzed：
1H NMR(DMSO,300Hz):δ (ppm)=9.06-8.92 (d, 1H), 8.57-8.46 (m, 2H), 8.37-8.26
(d,1H),8.24-8.01(m,15H),7.98-7.86(m,2H),7.84-7.12(m,45H),7.05-6.87(m,3H)；
MS(FAB):1544(M+)。
The synthesis of 3 compound 77 of embodiment
(1) synthesis of intermediate -20
[reaction equation 22]
In the three-necked flask of dry 2L, 24.4g (100mmol, 1.0eq.) 4- phenyl dibenzofurans is put into, with
The tetrahydrofuran dissolving of 300ml dryings, leads to nitrogen, is down to -10 DEG C, the LDA of 44ml2.5M (110mmol, 1.1eq.) is added dropwise, treats
Completion of dropwise addition continues to stir 1 hour at such a temperature, 30.1g (150mmol, 1.5eq.) iodine is added portionwise, removes cooling ring
Border, the reaction was continued overnight, and to the end of reaction, the HCl solution of 4M is added dropwise, stirs 1 hour, stands, layering, upper organic phase water
It washes 3 times, lower floor's organic phase is extracted with dichloromethane, is washed 3 times, merges organic phase, and dry, rotation removes solvent, is purified with chromatographic column,
Obtain 33.7g intermediate -20, yield 91%.
(2) synthesis of intermediate -21
[reaction equation 23]
33.7g (91mmol, 1.0eq.) intermediates -20 and 25.4g are added in dry 3L three-necked flasks
(100.1mmol, 1.1eq.) connection boric acid pinacol ester adds dry and degasification 1200ml1, and 4- dioxane is made molten
Agent, leads to nitrogen 15 minutes, adds in 1.5g catalyst Pd (dppf)2Cl2(2%mol) and 17.9g (182mmol, 2.0eq.) acetic acid
Potassium.100 DEG C are warming up to, reaction 5 hours overnight.It to the end of reaction, is cooled to room temperature, adds activated carbon, cross short column of silica gel, be spin-dried for filtering
Liquid with toluene and ethyl alcohol recrystallization, obtains 29.6g intermediate -21, yield 88%.
(3) synthesis of intermediate -22
[reaction equation 24]
13.8g (80.1mmol, 1.0eq.) para-bromoaniline and 29.6g (80.1mmol, 1.0eq.) intermediate -21 are added in
Into the three-necked flask of 2L, 900ml toluene and the dissolving of 90ml ethyl alcohol are added in, leads to nitrogen 15 minutes, 120.2ml 2M is added and contains
There is 33.2g (240.3mmol, 3.0eq.) K2CO3Aqueous solution, be eventually adding 1.9gPd (PPh3)4(2mol%).It is warming up to 110
DEG C, reaction terminates overnight.Add activated carbon adsorption, filter, rotation, with toluene and ethyl alcohol recrystallization, obtains 21.8g except solvent, drying
Intermediate -22, yield 81%.
(4) synthesis of intermediate -23
[reaction equation 25]
Added in dry 3L three-necked flasks 32g (100mmol, 1.0eq.) 2- bromo indoles simultaneously [3,2,1-JK] carbazole and
27.9g (110mmol, 1.1eq.) connection boric acid pinacol ester adds dry and degasification 1600ml Isosorbide-5-Nitraes-dioxane and makees
Solvent, leads to nitrogen 15 minutes, adds in 0.7g catalyst Pd (dppf)2Cl2(3%mol) and 19.6g (200mmol, 2.0eq.) second
Sour potassium.100 DEG C are warming up to, reaction 5 hours overnight.It to the end of reaction, is cooled to room temperature, adds activated carbon, cross short column of silica gel, be spin-dried for
Filtrate with toluene and ethyl alcohol recrystallization, obtains 31.6g intermediate -23, yield 86%.
(5) synthesis of intermediate -24
[reaction equation 26]
By 31.6g (86mmol, 1.0eq.) intermediates -23 and 26.8g (94.6mmol, 1.1eq.) to bromo-iodobenzene, add in
Into the three-necked flask of 3L, 1200ml toluene and the dissolving of 120ml ethyl alcohol are added in, leads to nitrogen 15 minutes, 129ml 2M is added and contains
There is 35.7g (258mmol, 3.0eq.) K2CO3Aqueous solution, be eventually adding 2.0gPd (PPh3)4(2mol%).It is warming up to 110
DEG C, reaction terminates overnight.Add activated carbon adsorption, filter, rotation, with toluene and ethyl alcohol recrystallization, obtains 26.9g except solvent, drying
Intermediate -24, yield 79%.
(6) synthesis of intermediate -25
[reaction equation 27]
21.8g (65.0mmol, 1.1eq.) intermediates -22 and 23.4g are added in dry 2L three-necked flasks
(59.1mmol, 1.0eq.) intermediate -24 add dry and degasification 900ml toluene and make solvent, lead to nitrogen 15 minutes.
Add 11.4g (118.2mmol, 2.0eq.) sodium tert-butoxide, 1.1g (2%mol) catalyst Pd2(dba)3With 4.8ml (4%
mol)P(t-bu)3Toluene solution (m/v, 10%).90 DEG C are warming up to, is reacted 2 hours.To the end of reaction, it is cooled to room temperature,
Add activated carbon adsorption, filter, rotation, with toluene and ethyl alcohol recrystallization, obtains 30.4g intermediate -25, yield 79% except solvent.
(7) synthesis of intermediate -26
[reaction equation 28]
30.4g (46.7mmol, 1.1eq.) intermediates -25 and 15.2g are added in dry 3L three-necked flasks
The bromo- 4- iodine biphenyl of (42.4mmol, 1.0eq.) 4- adds dry and degasification 900ml toluene and makees solvent, and logical nitrogen 15 divides
Clock.Add 8.1g (84.8mmol, 2.0eq.) sodium tert-butoxide, 0.8g (2%mol) catalyst Pd2(dba)3With 3.4ml (4%
mol)P(t-bu)3Toluene solution (m/v, 10%).90 DEG C are warming up to, is reacted 2 hours.To the end of reaction, it is cooled to room temperature,
Add activated carbon adsorption, filter, rotation, with toluene and ethyl alcohol recrystallization, obtains 26.9g intermediate -26, yield 72% except solvent.
(8) synthesis of intermediate -27
[reaction equation 29]
By 34.2g (200mmol, 1.0eq.) para-bromoaniline and 44.9g (220mmol, 1.1eq.) 5- phenyl -2- thiophene phenyls
Boric acid is added in the three-necked flask of 3L, is added in 1600ml toluene and the dissolving of 160ml ethyl alcohol, is led to nitrogen 15 minutes, adds
300ml 2M contain 82.9g (600mmol, 3.0eq.) K2CO3Aqueous solution, be eventually adding 4.6gPd (PPh3)4(2mol%).
110 DEG C are warming up to, reaction terminates overnight.Adding activated carbon adsorption, filter, rotation is dry except solvent, with toluene and ethyl alcohol recrystallization,
Obtain 39.2g intermediate -27, yield 78%.
(9) synthesis of intermediate -28
[reaction equation 30]
39.2g (44.5mmol, 1.0eq.) intermediates -26 and 12.3g are added in dry 3L three-necked flasks
(48.9mmol, 1.1eq.) intermediate -27 add dry and degasification 1000ml toluene and make solvent, lead to nitrogen 15 minutes.
Add 8.6g (89mmol, 2.0eq.) sodium tert-butoxide, 0.8g (2%mol) catalyst Pd2(dba)3With 3.6ml (4%mol) P
(t-bu)3Toluene solution (m/v, 10%).90 DEG C are warming up to, is reacted 2 hours.To the end of reaction, it is cooled to room temperature, adds activity
Charcoal adsorbs, and filters, and rotation, with toluene and ethyl alcohol recrystallization, obtains 34.2g intermediate -28, yield 73% except solvent.
(10) synthesis of intermediate -29
[reaction equation 31]
In the three-necked flask of dry 2L, input 18.2g (100mmol, 1.0eq.) 4- methyldiphenyls and furans are used
The tetrahydrofuran dissolving of 200ml dryings, leads to nitrogen, is down to -10 DEG C, the LDA of 44ml2.5M (110mmol, 1.1eq.) is added dropwise, treats
Completion of dropwise addition continues to stir 1 hour at such a temperature, 30.1g (150mmol, 1.5eq.) iodine is added portionwise, removes cooling ring
Border, the reaction was continued 19 hours overnight, and to the end of reaction, the HCl solution of 4M is added dropwise, stirs 1 hour, stands, layering, and upper strata is organic
It is mutually washed with water 3 times, lower floor's organic phase is extracted with dichloromethane, is washed 3 times, merges organic phase, and dry, rotation is except solvent, with chromatography
Column purifies, and obtains 26.8g intermediate -29, yield 87%.
(11) synthesis of compound 77
[reaction equation 32]
34.2g (32.5mmol, 1.0eq.) intermediates -28 and 10g are added in dry 3L three-necked flasks
(32.5mmol, 1.0eq.) intermediate -29 add dry and degasification 900ml toluene and make solvent, lead to nitrogen 15 minutes.
Add 6.2g (65mmol, 2.0eq.) sodium tert-butoxide, 0.6g (2%mol) catalyst Pd2(dba)3With 2.6ml (4%mol) P
(t-bu)3Toluene solution (m/v, 10%).90 DEG C are warming up to, is reacted 2 hours.To the end of reaction, it is cooled to room temperature, adds activity
Charcoal adsorbs, and filters, and rotation, with toluene and ethyl alcohol recrystallization, obtains 27.2g compounds 77, yield 68% except solvent.
Product spectrum data is analyzed：
1H NMR(DMSO,300Hz):δ (ppm)=8.25-8.16 (d, 2H), 8.12-7.97 (m, 4H), 7.95-7.78
(m,4H),7.72-7.11(m,40H),7.09-7.04(d,1H),7.02-6.92(m,3H),2.46-2.27(s,3H)；
MS(FAB):1232(M+)。
The synthesis of 4 compound 90 of embodiment
(1) synthesis of intermediate -30
[reaction equation 33]
By the bromo- 6- iodine dibenzofurans of 37.3g (100mmol, 1.1eq.) 4- and 32.7g (90.9mmol, 1.0eq.) 9,
9 '-spiral shell, two fluorenes -2- boric acid, is added in the three-necked flask of 3L, adds in 1400ml toluene and the dissolving of 140ml ethyl alcohol, leads to nitrogen 15
Minute, it adds 136.4ml 2M and contains 37.7g (272.7mmol, 3.0eq.) K2CO3Aqueous solution, be eventually adding 2.1gPd
(PPh3)4(2mol%).100 DEG C are warming up to, reaction terminates for 16 hours overnight.Add activated carbon adsorption, filter, rotation is done except solvent
It is dry, with toluene and ethyl alcohol recrystallization, obtain 40.3g intermediate -30, yield 79%.
(2) synthesis of intermediate -31
[reaction equation 34]
40.3g (71.8mmol, 1.0eq.) intermediates -30 and 20.1g are added in dry 3L three-necked flasks
(79mmol, 1.1eq.) connection boric acid pinacol ester adds dry and degasification 1200ml1, and 4- dioxane makees solvent, leads to
Nitrogen 15 minutes adds in 1.2g catalyst Pd (dppf)2Cl2
(2%mol) and 14.1g (143.6mmol, 2.0eq.) potassium acetate.100 DEG C are warming up to, reaction 5 hours overnight.It treats
Reaction terminates, and is cooled to room temperature, and adds activated carbon, crosses short column of silica gel, is spin-dried for filtrate, with toluene and ethyl alcohol recrystallization, obtains in 35g
Mesosome -31, yield 80%.
(3) synthesis of intermediate -32
[reaction equation 35]
By 35g (57.4mmol, 1.0eq.) intermediates -31 and 10.9g (63.2mmol, 1.1eq.) para-bromoaniline, add in
Into the three-necked flask of 2L, 900ml toluene and the dissolving of 90ml ethyl alcohol are added in, leads to nitrogen 15 minutes, 86.1ml 2M is added and contains
23.8g(172.2mmol,3.0eq.)K2CO3Aqueous solution, be eventually adding 1.3gPd (PPh3)4(2mol%).It is warming up to 100
DEG C, reaction terminates overnight.Add activated carbon adsorption, filter, rotation, with toluene and ethyl alcohol recrystallization, is obtained in 27g except solvent, drying
Mesosome -32, yield 82%.
(4) synthesis of intermediate -33
[reaction equation 36]
Added in dry 3L three-necked flasks 32g (100mmol, 1.0eq.) 2- bromo indoles simultaneously [3,2,1-JK] carbazole and
27.9g (110mmol, 1.1eq.) connection boric acid pinacol ester, adds dry and degasification 1600ml1, and 4- dioxane is made
Solvent, leads to nitrogen 15 minutes, adds in 0.7g catalyst Pd (dppf)2Cl2(3%mol) and 19.6g (200mmol, 2.0eq.) second
Sour potassium.100 DEG C are warming up to, reaction 5 hours overnight.It to the end of reaction, is cooled to room temperature, adds activated carbon, cross short column of silica gel, be spin-dried for
Filtrate with toluene and ethyl alcohol recrystallization, obtains 31.6g intermediate -33, yield 86%.
(5) synthesis of intermediate -34
[reaction equation 37]
By 31.6g (86mmol, 1.0eq.) intermediates -33 and 26.8g (94.6mmol, 1.1eq.) to bromo-iodobenzene, add in
Into the three-necked flask of 3L, 1200ml toluene and the dissolving of 120ml ethyl alcohol are added in, leads to nitrogen 15 minutes, 129ml 2M is added and contains
There is 35.7g (258mmol, 3.0eq.) K2CO3Aqueous solution, be eventually adding 2.0gPd (PPh3)4(2mol%).It is warming up to 110
DEG C, reaction terminates overnight.Add activated carbon adsorption, filter, rotation, with toluene and ethyl alcohol recrystallization, obtains 26.9g except solvent, drying
Intermediate -34, yield 79%.
(6) synthesis of intermediate -35
[reaction equation 38]
Added in dry 3L three-necked flasks 27g (47.1mmol, 1.1eq.) intermediates -32 and 17g (42.8mmol,
1.0eq.) intermediate -34 add dry and degasification 900ml toluene and make solvent, lead to nitrogen 15 minutes.Add 8.2g
(85.6mmol, 2.0eq.) sodium tert-butoxide, 0.8g (2%mol) catalyst Pd2(dba)3With 3.5ml (4%mol) P (t-bu)3's
Toluene solution (m/v, 10%).90 DEG C are warming up to, is reacted 2 hours.It to the end of reaction, is cooled to room temperature, adds activated carbon adsorption, take out
Filter, rotation, with toluene and ethyl alcohol recrystallization, obtain 29.3g intermediate -35, yield 77% except solvent.
(7) synthesis of intermediate -36
[reaction equation 39]
Added in dry 3L three-necked flasks 29.3g (33mmol, 1.0eq.) intermediates -35 and 13g (36.3mmol,
1.1eq.) the bromo- 4 '-iodine biphenyl of 4- adds dry and degasification 900ml toluene and makees solvent, leads to nitrogen 15 minutes.It adds
6.3g (66mmol, 2.0eq.) sodium tert-butoxide, 0.6g (2%mol) catalyst Pd2(dba)3With 2.7ml (4%mol) P (t-bu)3
Toluene solution (m/v, 10%).90 DEG C are warming up to, is reacted 2 hours.To the end of reaction, it is cooled to room temperature, adds activated carbon adsorption,
It filters, rotation, with toluene and ethyl alcohol recrystallization, obtains 28.1g intermediate -36, yield 76% except solvent.
(8) synthesis of intermediate -37
[reaction equation 40]
By 23.8g (100mmol, 1.0eq.) 9,9 '-dimethyl fluorene -2- boric acid and 31.8g (110mmol, 1.1eq.) 2-
Bromo- 5- iodothiophens, are added in the three-necked flask of 2L, add in 1100ml toluene and the dissolving of 110ml ethyl alcohol, lead to nitrogen 15 minutes,
It adds 150ml 2M and contains 41.5g (300mmol, 3.0eq.) K2CO3Aqueous solution, be eventually adding 2.3gPd (PPh3)4
(2mol%).100 DEG C are warming up to, reaction terminates overnight.Add activated carbon adsorption, filter, rotation is except solvent, drying, with toluene and second
Alcohol recrystallizes, and obtains 25.9g intermediate -37, yield 73%.
(9) synthesis of intermediate -38
[reaction equation 41]
By 25.9g (73mmol, 1.0eq.) intermediates -37 and 11g (80.3mmol, 1.1eq.) p-aminophenyl boric acid, add
Enter into the three-necked flask of 2L, add in 800ml toluene and the dissolving of 80ml ethyl alcohol, lead to nitrogen 15 minutes, add 109.5ml 2M
Contain 30.3g (219mmol, 3.0eq.) K2CO3Aqueous solution, be eventually adding 1.7gPd (PPh3)4(2mol%).It is warming up to 100
DEG C, reaction terminates overnight.Add activated carbon adsorption, filter, rotation, with toluene and ethyl alcohol recrystallization, obtains 22.8g except solvent, drying
Intermediate -38, yield 85%.
(10) synthesis of intermediate -39
[reaction equation 42]
28.1g (25.1mmol, 1.0eq.) intermediates -36 and 10.1g are added in dry 3L three-necked flasks
(27.6mmol, 1.1eq.) intermediate -38 add dry and degasification 800ml toluene and make solvent, lead to nitrogen 15 minutes.
Add 4.8g (50.2mmol, 2.0eq.) sodium tert-butoxide, 0.5g (2%mol) catalyst Pd2(dba)3With 2.0ml (4%mol)
P(t-bu)3Toluene solution (m/v, 10%).90 DEG C are warming up to, is reacted 2 hours.To the end of reaction, it is cooled to room temperature, adds work
Property charcoal absorption, filter, rotation with toluene and ethyl alcohol recrystallization, obtains 26.8g intermediate -39, yield 76% except solvent.
(11) synthesis of intermediate -40
[reaction equation 43]
In the three-necked flask of dry 2L, 24.4g (100mmol, 1.0eq.) 4- phenyl dibenzofurans is put into, is used
The tetrahydrofuran dissolving of 300ml dryings, leads to nitrogen, is down to -10 DEG C, the LDA of 44ml2.5M (110mmol, 1.1eq.) is added dropwise, treats
Completion of dropwise addition continues to stir 1 hour at such a temperature, 30.1g (150mmol, 1.5eq.) iodine is added portionwise, removes cooling ring
Border, the reaction was continued overnight, and to the end of reaction, the HCl solution of 4M is added dropwise, stirs 1 hour, stands, layering, upper organic phase water
It washes 3 times, lower floor's organic phase is extracted with dichloromethane, is washed 3 times, merges organic phase, and dry, rotation removes solvent, is purified with chromatographic column,
Obtain 32.6g intermediate -40, yield 88%.
(12) synthesis of compound 90
[reaction equation 44]
26.8g (19.1mmol, 1.0eq.) intermediates -39 and 7.1g are added in dry 3L three-necked flasks
(19.1mmol, 1.0eq.) intermediate -40 add dry and degasification 700ml toluene and make solvent, lead to nitrogen 15 minutes.
Add 3.7g (38.2mmol, 2.0eq.) sodium tert-butoxide, 0.3g (2%mol) catalyst Pd2(dba)3With 1.5ml (4%mol)
P(t-bu)3Toluene solution (m/v, 10%).90 DEG C are warming up to, is reacted 2 hours.To the end of reaction, it is cooled to room temperature, adds work
Property charcoal absorption, filter, rotation with toluene and ethyl alcohol recrystallization, obtains 23.6g compounds 90, yield 75% except solvent.
Product spectrum data is analyzed：
1HNMR(DMSO,300Hz):δ (ppm)=8.26-8.18 (d, 2H), 8.16-7.96 (m, 8H), 7.94-7.84
(m,7H),7.82-7.73(m,2H),7.71-7.09(m,49H),7.03-6.87(m,3H),1.78-1.43(s,6H)；
MS(FAB):1649(M+)。
Further, it is referred to such as the method for above formula 1-44, other that covered in general formula structure of the present invention is made and change
Close object, particularly particular compound 1-120.
The manufacture of 1 organic electroluminescence device of experimental example
Using ITO as reflecting layer anode grid substrate material, and it is surface-treated with N2 plasmas or UV-Ozone.
Above anode grid substrate, deposited to HIL layersThe HAT-CN of thickness.Above above-mentioned htl layer, by the chemical combination in the present invention
1 vacuum evaporation of objectThickness forms hole transmission layer.Vacuum evaporation TCTA is formed on above-mentioned hole transmission layer's
Electron-blocking layer, vapor deposition can form 9, the 10-Bis (2-naphthyl) of blue EML on above-mentioned electron-blocking layer
As luminescent layer, 2,5,8, the 11- tetrabutyl perylenes as dopant doping about 5% are formed anthraces (ADN)Luminescent layer.Above it by anthracene derivant and Liq with 1:1 ratio mixing vapor depositionThickness formed electronics
Transport layer is deposited on electron transfer layerLiq as electron injecting layer.Finally in cathode evaporationThickness
Silver.It is sealed in addition, being used in cathode surface containing UV curable adhesives water-absorbent material, to protect organic electroluminescence device not
It is influenced by the oxygen in air or moisture.
Experimental example 2-12
Respectively using compound 9,15,27,33,45,53,69,77,82,90 and 117 as hole transmission layer (HTL) substance,
Other parts are consistent with experimental example 1, produce the organic electroluminescence device of experimental example 2~12 accordingly.
Comparative example 1
Difference lies in replace the compound of the present invention as hole transmission layer, remaining and reality using NPD with experimental example 1
It is identical to test example 1.
The characteristic of the organic electroluminescence device of above-mentioned experimental example manufacture and the organic electroluminescence device of comparative example manufacture
Be current density be 10mA/cm2Under conditions of measure, the results are shown in Table 1.
1 different experiments group organic electroluminescence device performance test results of table
As seen from Table 1, the experimental example 1~12 of the organic electroluminescence device prepared using compound of the present invention,
Compared with reference examples, luminous efficiency significantly improves.Therefore, the compound of the present invention can reduce the driving voltage of device, reduce
The consumption of electric energy.Additionally by low electric drive, the service life of organic electroluminescence device also increases.
Although illustrate and describing the present invention with specific experiment example, it will be appreciated that without departing substantially from the present invention's
Many other change and modification can be made in the case of spirit and scope.It is, therefore, intended that in the following claims
Including belonging to all such changes and modifications in the scope of the invention.
Claims (10)
1. a kind of organic electroluminescent compounds, which is characterized in that the organic electroluminescent compounds structure is as follows：
Wherein, in formula (I), R1 is hydrogen, heavy hydrogen, the linear chain or branch chain type alkyl or hydrogen of C1~C20, phenyl, anilino-, diphenyl
Amido, 2- phenyl -3- aminopyridine bases, 3- amino bipyridyls, 2- phenyl-1-naphthylamine bases, 2- amido dinaphthyls, 2- phenyl -
1- amido phenanthryl, two phenanthryl of 3- amidos, 2- phenyl -1- amido anthryls, two anthryl of 2- amidos, phenanthridinyl, xenyl, pyridyl group,
One kind in pyrimidine radicals, or triazine radical；
R2For hydrogen, heavy hydrogen, the linear chain or branch chain type alkyl or hydrogen of C1~C20, phenyl, pyridyl group, naphthalene, phenanthryl, anthryl, phenanthridines
One kind in base, xenyl, pyridyl group, pyrimidine radicals or triazine radical；
R3For hydrogen, heavy hydrogen, the linear chain or branch chain type alkyl or hydrogen of C1~C20, phenyl, anilino-, diphenyl amido, 2- phenyl -3-
Aminopyridine base, 3- amino bipyridyls, 2- phenyl-1-naphthylamine bases, 2- amido dinaphthyls, 2- phenyl -1- amido phenanthryl, 3- amine
Two phenanthryl of base, 2- phenyl -1- amido anthryls, two anthryl of 2- amidos, phenanthridinyl, xenyl, pyridyl group, pyrimidine radicals or triazine
One kind of base；
L, m, n, o are respectively 0~4 integer.
2. organic electroluminescent compounds according to claim 1, which is characterized in that work as R1For phenyl, anilino-, hexichol
Base amido, 2- phenyl -3- aminopyridine bases, 3- amino bipyridyls, 2- phenyl-1-naphthylamine bases, 2- amido dinaphthyls, 2- benzene
Base -1- amido phenanthryl, two phenanthryl of 3- amidos, 2- phenyl -1- amido anthryls, two anthryl of 2- amidos, phenanthridinyl, xenyl, pyridine
When base, pyrimidine radicals or triazine radical, the hydrogen more than one of them is by the linear or branched alkyl group of C1-C20, the cycloalkanes of C3-C24
Base, the alkoxy of C1-C20, halogen, CN, CF3, Si (CH3)3, naphthalene, anthryl, phenanthryl, dibenzofuran group, fluorenyl, carbazole
Base, Spirofluorene-based and nuclear atom number 5-20 heteroaryl are substituted or non-substituted.
3. organic electroluminescent compounds according to claim 1, which is characterized in that work as R2For phenyl, pyridyl group, naphthalene,
When phenanthryl, anthryl, phenanthridinyl, xenyl, pyridyl group, pyrimidine radicals or triazine radical, the hydrogen more than one of them is by C1~C20's
Linear or branched alkyl group, the cycloalkyl of C3-C24, the alkoxy of C1-C20, halogen, CN, CF3, Si (CH3)3, naphthalene, anthryl, phenanthrene
Base, benzofuranyl, dibenzofuran group, fluorenyl, carbazyl, the heteroaryl that Spirofluorene-based and nuclear atom number is 5-20 replace
It is or non-substituted.
4. organic electroluminescent compounds according to claim 3, which is characterized in that work as R3For phenyl, anilino-, hexichol
Base amido, 2- phenyl -3- aminopyridine bases, 3- amino bipyridyls, 2- phenyl-1-naphthylamine bases, 2- amido dinaphthyls, 2- benzene
Base -1- amido phenanthryl, two phenanthryl of 3- amidos, 2- phenyl -1- amido anthryls, two anthryl of 2- amidos, phenanthridinyl, xenyl, pyridine
When base, pyrimidine radicals or triazine radical, the hydrogen more than one of them is by the linear or branched alkyl group of C1-C20, the cycloalkanes of C3-C24
Base, the alkoxy of C1-C20, halogen, CN, CF3, Si (CH3)3, naphthalene, anthryl, phenanthryl, dibenzofuran group, fluorenyl, carbazole
Base, Spirofluorene-based and nuclear atom number 5-20 heteroaryl are substituted or non-substituted.
5. according to the organic electroluminescent compounds described in any one of claim 1-4, which is characterized in that formula (I) compound
For any one of following compound：
6. a kind of organic electroluminescence device of the organic electroluminescent compounds comprising described in any one of claim 1-5.
7. organic electroluminescence device according to claim 6, which is characterized in that the organic electroluminescence device packet
It includes：
What anode, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and cathode were sequentially accumulated
Construction；
Wherein, electron-blocking layer is also optionally provided between anode and luminescent layer；
Hole blocking layer is also optionally provided between cathode and luminescent layer；
Cathode surface is also optionally provided with coating.
8. organic electroluminescence device according to claim 7, which is characterized in that the hole transmission layer, electronics barrier
At least one layer in layer, electron transfer layer or hole group interlayer includes the organic electroluminescence described in any one of claim 1-5
Luminophor.
9. a kind of ORGANIC ELECTROLUMINESCENCE DISPLAYS of the organic electroluminescence device comprising described in any one of claim 6-8 is set
It is standby.
10. the organic electroluminescent compounds described in any one of claim 1-5 are in organic electroluminescence device is prepared
Using；
And/or the organic electroluminescent compounds described in any one of claim 1-5 are set in preparation ORGANIC ELECTROLUMINESCENCE DISPLAYS
Application in standby.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711430621.3A CN108178763A (en) | 2017-12-26 | 2017-12-26 | A kind of organic electroluminescent compounds and the organic electroluminescence device using the compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711430621.3A CN108178763A (en) | 2017-12-26 | 2017-12-26 | A kind of organic electroluminescent compounds and the organic electroluminescence device using the compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108178763A true CN108178763A (en) | 2018-06-19 |
Family
ID=62547042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711430621.3A Pending CN108178763A (en) | 2017-12-26 | 2017-12-26 | A kind of organic electroluminescent compounds and the organic electroluminescence device using the compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108178763A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111004243A (en) * | 2019-12-02 | 2020-04-14 | 武汉华星光电半导体显示技术有限公司 | Indolo [3,2,1-jk ] carbazole derivative, organic electroluminescent device, and display panel |
| CN111269174A (en) * | 2020-03-30 | 2020-06-12 | 北京燕化集联光电技术有限公司 | Organic electroluminescent material and application thereof |
| CN111747915A (en) * | 2019-03-29 | 2020-10-09 | 南京高光半导体材料有限公司 | Organic electroluminescent compound, organic electroluminescent device and application thereof |
| KR102212689B1 (en) * | 2020-08-25 | 2021-02-05 | 주식회사 이엘엠 | Composition For Capping Layer of Organic Light Emitting Diode and Organic Light Emitting Diode Having The Same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103130812A (en) * | 2013-03-05 | 2013-06-05 | 华东师范大学 | Indolo[3,2,1-jk]carbazole derivative, preparation method and application |
| CN106397301A (en) * | 2015-08-01 | 2017-02-15 | 南京高光半导体材料有限公司 | Novel organic compound and materials for organic electroluminescent devices comprising the same and organic electroluminescent devices comprising the same |
| CN106397223A (en) * | 2015-08-01 | 2017-02-15 | 南京高光半导体材料有限公司 | Organic compound, materials for organic electroluminescent devices comprising compound and organic electroluminescent devices comprising materials |
-
2017
- 2017-12-26 CN CN201711430621.3A patent/CN108178763A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103130812A (en) * | 2013-03-05 | 2013-06-05 | 华东师范大学 | Indolo[3,2,1-jk]carbazole derivative, preparation method and application |
| CN106397301A (en) * | 2015-08-01 | 2017-02-15 | 南京高光半导体材料有限公司 | Novel organic compound and materials for organic electroluminescent devices comprising the same and organic electroluminescent devices comprising the same |
| CN106397223A (en) * | 2015-08-01 | 2017-02-15 | 南京高光半导体材料有限公司 | Organic compound, materials for organic electroluminescent devices comprising compound and organic electroluminescent devices comprising materials |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111747915A (en) * | 2019-03-29 | 2020-10-09 | 南京高光半导体材料有限公司 | Organic electroluminescent compound, organic electroluminescent device and application thereof |
| CN111004243A (en) * | 2019-12-02 | 2020-04-14 | 武汉华星光电半导体显示技术有限公司 | Indolo [3,2,1-jk ] carbazole derivative, organic electroluminescent device, and display panel |
| CN111004243B (en) * | 2019-12-02 | 2021-08-03 | 武汉华星光电半导体显示技术有限公司 | Indolo [3,2,1-jk ] carbazole derivative, organic electroluminescent device, and display panel |
| CN111269174A (en) * | 2020-03-30 | 2020-06-12 | 北京燕化集联光电技术有限公司 | Organic electroluminescent material and application thereof |
| KR102212689B1 (en) * | 2020-08-25 | 2021-02-05 | 주식회사 이엘엠 | Composition For Capping Layer of Organic Light Emitting Diode and Organic Light Emitting Diode Having The Same |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107936957B (en) | Organic electroluminescent compound, organic electroluminescent device and application thereof | |
| JP5989000B2 (en) | Aromatic amine derivative, material for organic electroluminescence device, and organic electroluminescence device | |
| TWI629257B (en) | Compound and organic electronic device using the same | |
| CN106866498A (en) | Organic compound, organic electroluminescence device and its application | |
| EP2754661A1 (en) | Nitrogen-containing heteroaromatic ring compound | |
| CN108178763A (en) | A kind of organic electroluminescent compounds and the organic electroluminescence device using the compound | |
| KR20110071127A (en) | Aromatic amine derivative, and organic electroluminescent element comprising same | |
| TW201329059A (en) | Aromatic amine derivative, material for organic electroluminescent element, and organic electroluminescent element | |
| CN108101897B (en) | Novel organic electroluminescent compound and organic electroluminescent device containing same | |
| KR20120020901A (en) | Novel compounds for organic electronic material and organic electroluminescent device using the same | |
| CN108084091A (en) | A kind of novel electroluminescent compound and its application and use its organic electroluminescence device | |
| CN108101896B (en) | Organic electroluminescent compound, organic electroluminescent device and application thereof | |
| CN108084180A (en) | A kind of novel electroluminescent compound and the organic electroluminescence device using the organic electroluminescent compounds | |
| CN108164544A (en) | Organic electroluminescent compounds, organic electroluminescence device and its application | |
| CN108117539A (en) | A kind of organic electroluminescent compounds, organic electroluminescence device and its application | |
| TWI641598B (en) | Compound and organic electronic device using the same | |
| TWI653211B (en) | Compound and its organic electronic device | |
| KR20150132095A (en) | Amine compound having hetero-fused ring and organic electroluminescent element using amine compound | |
| CN107778309B (en) | Quinoline derivative and application thereof | |
| TW201835062A (en) | Compound and organic electronic device using the same | |
| CN109485665A (en) | Compound and application thereof and organic electroluminescence device | |
| WO2013077385A1 (en) | Aromatic amine derivative and organic electroluminescence device using same | |
| CN108101898A (en) | A kind of novel electroluminescent compound and include its organic electroluminescence device | |
| KR20190138612A (en) | Compound and organic electronic device comprising the same | |
| CN108164543A (en) | A kind of organic electroluminescent compounds, organic electroluminescence device and its application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20180619 |