CN104744347B - Dianthracene compound with pyridyl at tail end and application thereof - Google Patents

Dianthracene compound with pyridyl at tail end and application thereof Download PDF

Info

Publication number
CN104744347B
CN104744347B CN201410111568.0A CN201410111568A CN104744347B CN 104744347 B CN104744347 B CN 104744347B CN 201410111568 A CN201410111568 A CN 201410111568A CN 104744347 B CN104744347 B CN 104744347B
Authority
CN
China
Prior art keywords
compound
substituted
formula
an9b
preparation
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.)
Active
Application number
CN201410111568.0A
Other languages
Chinese (zh)
Other versions
CN104744347A (en
Inventor
黄达
孙艳雪
谭玉东
靳灿辉
孙仲猛
曹林法
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jiangsu Hecheng Advanced Materials Co ltd
Original Assignee
Jiangsu Hecheng Advanced Materials Co ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Jiangsu Hecheng Advanced Materials Co ltd filed Critical Jiangsu Hecheng Advanced Materials Co ltd
Priority to CN201410111568.0A priority Critical patent/CN104744347B/en
Publication of CN104744347A publication Critical patent/CN104744347A/en
Application granted granted Critical
Publication of CN104744347B publication Critical patent/CN104744347B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/127—Preparation from compounds containing pyridine rings
    • 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
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The invention provides a dianthracene compound shown as a general formula I, wherein L1And L2Represents a single bond, a substituted or unsubstituted heterocyclic aromatic group of C2-C60, or a substituted or unsubstituted hydrocarbon aromatic group of C6-C60; l is3Represents a substituted or unsubstituted heterocyclic aromatic group of C2-C60 or a substituted or unsubstituted hydrocarbon aromatic group of C6-C60; l is1、L2And L3Is not simultaneously
Figure DDA0000481033220000011
R10、R18、R21、R23‑R28Represents hydrogen, halogen, substituted or unsubstituted alkyl or alkoxy of C1 to C10. The compound has good luminescence property, high electron transport capability and excellent solubility, and can be used for luminescent materials, electron transport materials and hole blocking materials in the field of electroluminescence. The invention also provides an organic electroluminescent device comprising at least a pair of electrodes and an organic light-emitting medium between the electrodes, the organic light-emitting medium comprising at least one dianthracene compound of the invention.

Description

Dianthracene compound with pyridyl at tail end and application thereof
Technical Field
The invention relates to a dianthracene compound with a pyridyl terminal, which can be applied to the field of electroluminescence.
Background
Organic electroluminescent diodes (OLEDs) have been published since 1987 in the application of physical bulletin (appl. phys. lett.,1987,51,913) by dunqing cloud, and have received great attention from both academic and industrial circles because of their advantages of self-luminescence, low voltage dc driving, and full curing. In the field of display, the OLED has the characteristics of a cathode ray tube and a liquid crystal display, has large visual angle, low power consumption and bright color, and is known as a next generation of dream display. In the field of illumination, as the only technology capable of really realizing a surface light source, the OLED has the advantages of soft and non-glaring light emission, green and environmental protection, is most close to a healthy light source of natural light, and is known as the most energy-saving and healthy illumination light source in the human development history.
The adoption of high-performance luminescent materials is an important basis for the preparation of OLED devices. The existing OLED materials are mainly divided into small molecular materials and high molecular materials, the small molecular materials are easy to crystallize, the solubility is poor, the light-emitting efficiency of the high molecular materials is low, and the industrial production is not facilitated. Therefore, finding an organic material with high luminous efficiency and good solubility becomes a key problem in the technical field of OLED materials.
The anthracene compound which is found at present is a typical luminescent system, and is suitable for being used as an electroluminescent material. The 9, 10-diaryl anthracene has good stability and luminous efficiency, and is an excellent blue luminescent material. Due to the excellent steric hindrance effect of the 2, 9' -dianthracene compounds, the red shift of the compound film spectrum is very small compared with the PL solution spectrum, and the main luminescence peak is kept at about 450 nm. Meanwhile, the literature (chem.lett.,2008,37,1150-1151) also reports that such compounds have excellent thermal stability.
However, in the existing literature reports, 2, 9' -dianthracene compounds are mostly hydrocarbon type compounds, and only have single luminescence property, and the transmission property is poor, and the application to the field of electroluminescence can cause the problems of increased device power consumption, shortened product life, chromaticity deviation and the like, and the development of materials with both luminescence property and transmission property is urgently needed. CN101395105A reports dianthracene compounds containing carbazole and benzimidazole groups, but the synthesis route is complex, the solubility is low, the purification is difficult, and the industrial production is not facilitated.
The compound containing pyridyl is a typical electron-deficient system and has good electron accepting capability. The compound containing pyridyl is a typical electron-deficient system and has good electron accepting capability. An electron transport material containing a pyridine group reported in the literature (chem.mater., 2011,23, 621-630) shows high thermal stability, excellent hole blocking and exciton blocking capabilities and excellent electron transport capability. The pyridine group-containing electron transport materials reported in the literature (adv.Funct.Mater.,2011,21, 1881-1886) show excellent electron transport performance and electron injection performance, and meanwhile, the materials have good electrochemical stability and prolonged service life.
The invention introduces the electron-deficient pyridyl group on the basis of the dianthracene derivative with a twisted structure, so that the compound has good luminescent property and good transmission property. Overcomes the defect of poor transmission performance of the traditional hydrocarbon dianthracene compounds.
In addition, the compound of the present invention contains an alkyl group in many cases in view of the ease of industrial production.
Disclosure of Invention
The invention aims to provide a novel fluorescent compound, which introduces an electron-deficient pyridyl group on the basis of a dianthracene derivative with a twisted structure, so that the compound has good luminous performance and good transmission performance and can be used as a luminous layer, an electron transmission layer and a hole blocking layer in an organic luminous medium.
In order to accomplish the above object, the present invention provides a dianthracene compound represented by the general formula I:
Figure BDA0000481033200000021
wherein the content of the first and second substances,
L1and L2The same or different, independently represent a single bond, a substituted or unsubstituted heterocyclic aromatic group of C2-C60, or a substituted or unsubstituted hydrocarbon aromatic group of C6-C60;
L3independently represent a substituted or unsubstituted heterocyclic aromatic group of C2-C60 or a substituted or unsubstituted hydrocarbon aromatic group of C6-C60;
provided that L1, L2 and L3 are not simultaneously
Figure BDA0000481033200000022
R10、R11、R12、R13、R14、R15、R16、R17、R18、R21、R23、R24、R25、R26、R27And R28Identical or different, independently of one another, represent hydrogen, halogen, substituted or unsubstituted alkyl of C1 to C10, or substituted or unsubstituted alkoxy of C1 to C10.
In some embodiments, the L is1And L2The same applies to a single bond, a substituted or unsubstituted heterocyclic aromatic group having C2-C60, or a substituted or unsubstituted hydrocarbon aromatic group having C6-C60.
In some embodiments, the L is1、L2And L3Independently of one another, the following aromatic radicals:
Figure BDA0000481033200000031
wherein the content of the first and second substances,
ra, Rb, Rc, Rd, which are identical or different, independently of one another denote hydrogen, halogen, substituted or unsubstituted alkyl of C1 to C30 or substituted or unsubstituted alkoxy of C1 to C30.
In some embodiments, the L is1、L2And L3Independently of one another, the following aromatic radicals:
Figure BDA0000481033200000041
wherein the content of the first and second substances,
ra, Rb, Rc can be hydrogen, halogen, substituted or unsubstituted alkyl of C1-C30, or substituted or unsubstituted alkoxy of C1-C30.
In some embodiments, the L1, L2, and L3 are each independently selected from
Figure BDA0000481033200000042
Figure BDA0000481033200000043
Figure BDA0000481033200000051
In some embodiments, R26And R27Each independently selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl.
In another aspect, the invention provides two methods for synthesizing dianthracene compounds of the formula I, one method being as follows:
1) reacting a compound of formula 4
Figure BDA0000481033200000052
And a compound of formula 5
Figure BDA0000481033200000053
Obtaining the compound of formula 2 by reaction
Figure BDA0000481033200000054
2) Reacting a compound of formula 6
Figure BDA0000481033200000055
And a compound of formula 7
Figure BDA0000481033200000056
Obtaining the intermediate of the formula 8 through suzuki coupling reaction
Figure BDA0000481033200000061
Subjecting the intermediate of formula 8 to a boration reaction to obtain a compound of formula 3
Figure BDA0000481033200000062
3) Carrying out suzuki coupling reaction on the compound shown in the formula 2 and the compound shown in the formula 3 to obtain a dianthracene compound shown in the general formula I:
Figure BDA0000481033200000063
wherein the content of the first and second substances,
X1，X2，X3is halogen.
The other method comprises the following steps:
1) reacting a compound of formula 2
Figure BDA0000481033200000064
And a compound of formula 9
Figure BDA0000481033200000065
Obtaining the compound of formula 10 by coupling reaction
Figure BDA0000481033200000071
Obtaining the compound of formula 11 by bromination
Figure BDA0000481033200000072
2) The compounds of formula 11 and 12
Figure BDA0000481033200000073
Obtaining the compound of formula 13 by a coupling reaction
Figure BDA0000481033200000074
Bromination to give the compound of formula 14
Figure BDA0000481033200000075
3) The compounds of formula 14 and formula 15
Figure BDA0000481033200000076
Through coupling reaction, the dianthracene compound shown in the general formula I is obtained
Figure BDA0000481033200000077
Wherein the content of the first and second substances,
X4is halogen.
The dianthracene compounds shown as the general formula I are used as luminescent materials, electron transport materials or hole blocking materials in the preparation of organic electroluminescent devices.
In another aspect, the present invention provides an organic electroluminescent device comprising a pair of electrodes and an organic light-emitting medium between the electrodes, wherein the organic light-emitting medium comprises at least one dianthracene compound of the present invention.
In some embodiments, the dianthracene compound is located in an electron transport layer in the organic light emitting medium.
In some embodiments, the dianthracene compound is located in a light-emitting layer in the organic light-emitting medium.
In some embodiments, the dianthracene compounds act as blue light emitting materials.
In some embodiments, the dianthracene compound serves as a host light-emitting material for the light-emitting layer.
The invention provides a method for comparing electron transport performance of materials, which adopts a quantum chemistry method to obtain the difference of the electron transport performance between compounds by comparing the electron recombination energy of the compounds within a certain precision range.
The organic compound has good transmission performance and luminescence performance, and can be used as a luminescent layer, an electron transmission layer and a hole blocking layer in an organic electroluminescent device.
Drawings
FIG. 1 shows NMR data of a compound according to the invention synthesized in example 34.
FIG. 2 shows NMR data of a compound according to the invention synthesized in example 36.
FIG. 3 shows NMR data of a compound according to the invention synthesized in example 37.
FIG. 4 shows NMR data of the compound according to the invention synthesized in example 38.
FIG. 5 shows NMR data of the compound according to the invention synthesized in example 42.
FIG. 6 shows NMR data of the compound according to the invention synthesized in example 44.
FIG. 7 shows NMR data of the compound according to the invention synthesized in example 46.
FIG. 8 shows NMR data of a compound according to the invention synthesized in example 47.
FIG. 9 shows spectral data of a compound according to the invention synthesized in example 37.
Detailed Description
Example 1
Preparation of Compound HP-NP14-PY4
Figure BDA0000481033200000091
[HP-NP14-PY4]
1, 4-dibromonaphthalene (4 mmol,1.14 g), pyridine-4-boronic acid (4 mmol,0.49 g) and tetrakis (triphenylphosphine) palladium (100 mg) were mixed, and a mixed solution of toluene (6 ml)/ethanol (6ml)/2M Na2CO3(1ml) was added. The reaction was stirred at 100 ℃ for 4 hours and then cooled to room temperature. The reaction was diluted with water (50 ml) and extracted with ethyl acetate (3 x 50 ml). The organic phase was dried over anhydrous magnesium sulfate, concentrated and chromatographed on silica gel to give an off-white solid (0.56 g, 50% yield).
Example 2
Preparation of Compound HP-NP14-PY3
Figure BDA0000481033200000092
[HP-NP14-PY3]
The same reaction as in example 1 was carried out except that pyridine-3-boronic acid was used instead of pyridine-4-boronic acid, to obtain the compound HP-NP14-PY 3.
Example 3
Preparation of Compound HP-NP14-PY2
Figure BDA0000481033200000093
[HP-NP14-PY2]
The same reaction as in example 1 was carried out except that pyridine-2-boronic acid was used instead of pyridine-4-boronic acid, to obtain the compound HP-NP14-PY 2.
Example 4
Preparation of the Compound HP-2PH44-PY4
Figure BDA0000481033200000094
[HP-2PH44-PY4]
The same reaction as in example 1 was carried out except that 4, 4-dibromobiphenyl was used in place of 1, 4-dibromonaphthalene to obtain HP-2PH44-PY 4.
Example 5
Preparation of the Compound HP-2PH44-PY3
Figure BDA0000481033200000095
[HP-2PH44-PY3]
The same reaction as in example 1 was carried out except for using 4, 4-dibromobiphenyl instead of 1, 4-dibromonaphthalene and pyridine-3-boronic acid instead of pyridine-4-boronic acid, to obtain the compound HP-2PH44-PY 3.
Example 6
Preparation of the Compound HP-2PH44-PY2
Figure BDA0000481033200000096
[HP-2PH44-PY2]
The same reaction as in example 1 was carried out except for using 4, 4-dibromobiphenyl instead of 1, 4-dibromonaphthalene and pyridine-2-boronic acid instead of pyridine-4-boronic acid, to obtain the compound HP-2PH44-PY 3.
Example 7
Preparation of the Compound HP-PH44-PY4
Figure BDA0000481033200000101
[HP-PH44-PY4]
The same reaction as in example 1 was carried out except that 1, 4-dibromobenzene was used instead of 1, 4-dibromonaphthalene, to obtain HP-PH44-PY 4.
Example 8
Preparation of the Compound HP-PH44-PY3
Figure BDA0000481033200000102
[HP-PH44-PY3]
The same reaction as in example 1 was carried out except that 4, 4-dibromobiphenyl was used instead of 1, 4-dibromonaphthalene and pyridine-3-boronic acid was used instead of pyridine-4-boronic acid, to obtain the compound HP-PH44-PY 3.
Example 9
Preparation of the Compound HP-PH44-PY2
Figure BDA0000481033200000103
[HP-PH44-PY2]
The same reaction as in example 1 was carried out except that 4, 4-dibromobiphenyl was used instead of 1, 4-dibromonaphthalene and pyridine-2-boronic acid was used instead of pyridine-4-boronic acid, to obtain the compound HP-PH44-PY 2.
Example 10
Preparation of Compound HP-AN-NP14-PY4
Figure BDA0000481033200000104
[HP-AN-NP14-PY4]
HP-NP14-PY4 (1 mmol, 284 mg) was dissolved in anhydrous tetrahydrofuran (10 ml), 1.6M butyllithium solution (1 mmol, 0.63 ml) was added dropwise at 78 deg.C, then 2-bromoanthraquinone (0.5 mmol, 144 mg) was added, warmed to room temperature and stirred for 2 hours, water (20 ml) was added and extracted with dichloromethane (3 x 40 ml), the organic phase was dried over anhydrous magnesium sulfate and concentrated to give a dark solid. The dark solid was dissolved in acetic acid (30 ml) and potassium iodide (3 mmol, 500 mg), sodium hypophosphite monohydrate (6 mmol,1.1 g) was added, stirred at 120 ℃ for 3 hours and then cooled to room temperature, whereupon a solid precipitated. The filtered solid was washed with cold water (3 × 20 ml) and dried to give HP-AN-NP14-PY4 (300 mg, 90% yield) as a white solid.
Example 11
Preparation of Compound HP-AN-NP14-PY3
Figure BDA0000481033200000111
[HP-AN-NP14-PY3]
The same reaction as in example 10 was carried out except that HP-NP14-PY3 was used in place of HP-NP14-PY4, to give the compound HP-AN-NP14-PY 3.
Example 12
Preparation of Compound HP-AN-NP14-PY2
Figure BDA0000481033200000112
[HP-AN-NP14-PY2]
The same reaction as in example 10 was carried out except that HP-NP14-PY2 was used in place of HP-NP14-PY4, to give the compound HP-AN-NP14-PY 2.
Example 13
Preparation of the Compound HP-AN-PH44-PY4
Figure BDA0000481033200000113
[HP-AN-PH44-PY4]
The same reaction as in example 10 was carried out except that HP-PH44-PY4 was used in place of HP-NP14-PY4, to give HP-AN-PH44-PY 4.
Example 14
Preparation of the Compound HP-AN-PH44-PY3
Figure BDA0000481033200000114
[HP-AN-PH44-PY3]
The same reaction as in example 10 was carried out except that HP-PH44-PY3 was used in place of HP-NP14-PY4, to give HP-AN-PH44-PY 3.
Example 15
Preparation of the Compound HP-AN-2PH44-PY4
Figure BDA0000481033200000115
[HP-AN-2PH44-PY4]
The same reaction as in example 10 was carried out except that HP-2PH44-PY4 was used in place of HP-NP14-PY4, to give HP-AN-2PH44-PY 4.
Example 16
Preparation of the Compound HP-AN-2PH44-PY3
Figure BDA0000481033200000121
[HP-AN-2PH44-PY3]
The same reaction as in example 10 was carried out except that HP-2PH44-PY3 was used in place of HP-NP14-PY4, to give HP-AN-2PH44-PY 3.
Example 17
Preparation of the Compound HP-ANme-PH44-PY4
Figure BDA0000481033200000122
[HP-ANme-PH44-PY4]
The same reaction as in example 10 was carried out except for using HP-PH44-PY4 in place of HP-NP14-PY4 and 2-bromo-6-methylanthraquinone in place of 2-bromoanthraquinone, to obtain HP-ANme-PH44-PY 4.
Example 18
Preparation of the Compound HP-ANme-PH44-PY3
Figure BDA0000481033200000123
[HP-ANme-PH44-PY4]
The same reaction as in example 10 was carried out except for using HP-PH44-PY3 in place of HP-NP14-PY4 and 2-bromo-6-methylanthraquinone in place of 2-bromoanthraquinone, to obtain HP-ANme-PH44-PY 3.
Example 19
Preparation of the Compound HP-ANet-2PH44-PY4
Figure BDA0000481033200000124
[HP-ANet-2PH44-PY4]
The same reaction as in example 10 was carried out except for using HP-2PH44-PY4 in place of HP-NP14-PY4 and 2-bromo-6 ethylanthraquinone in place of 2-bromoanthraquinone, to obtain the compound HP-ANet-2PH44-PY 4.
Example 20
Preparation of the Compound HP-AN9-PH44-PY4
Figure BDA0000481033200000131
[HP-AN9-PH44-PY4]
1, 4-dibromoanthracene (4 mmol,1.34 g), 4- (4-pyridyl) -phenylboronic acid (4 mmol,0.80 g) and tetrakis (triphenylphosphine) palladium (100 mg) were mixed, and a mixed solution of toluene (6 ml)/ethanol (6ml)/2M Na2CO3(1ml) was added. The reaction was stirred at 100 ℃ for 4 hours under nitrogen blanket and then cooled to room temperature. The reaction was diluted with water (50 ml) and extracted with ethyl acetate (3 x 50 ml). The organic phase was dried over anhydrous magnesium sulfate, concentrated and chromatographed on silica gel to give HP-AN9-pH44-PY4 as a yellow solid (0.66, 40% yield).
Example 21
Compound HP-AN9-PH44-Preparation of PY3
Figure BDA0000481033200000132
[HP-AN9-PH44-PY3]
The same reaction as in example 20 was conducted except that 4- (3-pyridyl) -phenylboronic acid was used instead of 4- (4-pyridyl) -phenylboronic acid, to give a compound HP-AN9-PH44-PY 3.
Example 22
Preparation of the Compound HP-AN9-PH44-PY2
Figure BDA0000481033200000133
[HP-AN9-PH44-PY2]
The same reaction as in example 20 was conducted except that 4- (2-pyridyl) -phenylboronic acid was used instead of 4- (4-pyridyl) -phenylboronic acid, to give a compound HP-AN9-PH44-PY 2.
Example 23
Preparation of the Compound HP-AN9-PH43-PY4
Figure BDA0000481033200000134
[HP-AN9-PH43-PY4]
The same reaction as in example 20 was conducted except that 3- (4-pyridyl) -phenylboronic acid was used instead of 4- (4-pyridyl) -phenylboronic acid, to give a compound HP-AN9-PH43-PY 4.
Example 24
Preparation of the Compound HP-AN9-2PH44-PY4
Figure BDA0000481033200000141
[HP-AN9-2PH44-PY4]
The same reaction as in example 20 was conducted except that 4- (4-pyridyl) -phenylboronic acid was used instead of 4- (4-pyridyl) -phenylboronic acid, to give a compound HP-AN9-2PH44-PY 4.
Example 25
Compound HP-AN9-2PH44-Preparation of PY3
Figure BDA0000481033200000142
[HP-AN9-2PH44-PY3]
The same reaction as in example 20 was conducted except that 4- (3-pyridyl) -phenylboronic acid was used instead of 4- (4-pyridyl) -phenylboronic acid, to give a compound HP-AN9-2PH44-PY 3.
Example 26
Preparation of the Compound HP-AN9-NP14-PY3
Figure BDA0000481033200000143
[HP-AN9-NP14-PY3]
The same reaction as in example 20 was conducted except that 4- (3-pyridyl) -1-naphthoic acid was used instead of 4- (4-pyridyl) -phenylboronic acid, to give a compound HP-AN9-NP14-PY 3.
Example 27
Preparation of the Compound HP-AN9B-PH44-PY4
Figure BDA0000481033200000144
[HP-AN9B-PH44-PY4]
The compound HP-AN9-PH44-PY4 (3 mmol,1.23 g) was dissolved in anhydrous tetrahydrofuran (25 ml), 1.6M butyllithium solution (3.6 mmol, 2.3 ml) was added dropwise at 78 deg.C, trimethyl borate (4.5 mmol,0.5 ml) was added dropwise with stirring under nitrogen for 2 hours, stirring was continued for 2 hours under nitrogen, 1M hydrochloric acid solution (30 ml) was quenched, water (100 ml) was added to precipitate, and the solid was washed with n-hexane (3 x 20 ml) to give HP-AN9B-PH44-PY4 (0.78 g, 70% yield) as a white powder.
Example 28
Preparation of the Compound HP-AN9B-PH44-PY3
Figure BDA0000481033200000145
[HP-AN9B-PH44-PY3]
The same reaction as in example 27 was carried out except that HP-AN9-PH44-PY3 was used in place of HP-AN9-PH44-PY4 to obtain HP-AN9B-PH44-PY 3.
Example 29
Preparation of the Compound HP-AN9B-PH44-PY2
Figure BDA0000481033200000151
[HP-AN9B-PH44-PY2]
The compound HP-AN9B-PH44-PY2 was obtained by the same reaction as in example 27 except that HP-AN9-PH43-1 was used in place of HP-AN9-PH44-PY 4.
Example 30
Preparation of the Compound HP-AN9B-PH43-PY4
Figure BDA0000481033200000152
[HP-AN9B-PH43-PY4]
The same reaction as in example 27 was carried out except that HP-AN9-PH43-PY4 was used in place of HP-AN9-PH44-PY4 to obtain HP-AN9B-PH43-PY 4.
Example 31
Preparation of the Compound HP-AN9B-2PH44-PY4
Figure BDA0000481033200000153
[HP-AN9B-2PH44-PY4]
The same reaction as in example 27 was carried out except that HP-AN9-2PH44-PY4 was used in place of HP-AN9-PH44-PY4 to obtain HP-AN9B-2PH44-PY 4.
Example 32
Preparation of the Compound HP-AN9B-2PH44-PY3
Figure BDA0000481033200000154
[HP-AN9B-2PH44-PY3]
The same reaction as in example 27 was carried out except that HP-AN9-2PH44-PY3 was used in place of HP-AN9-PH44-PY4 to obtain HP-AN9B-2PH44-PY 3.
Example 33
Preparation of the Compound HP-AN9B-NP14-PY3
Figure BDA0000481033200000155
[HP-AN9B-NP14-PY3]
The same reaction as in example 27 was carried out except that HP-AN9-NP14-PY3 was used in place of HP-AN9-PH44-PY4 to obtain HP-AN9B-NP14-PY 3.
Example 34
Preparation of the Compound HP-L-NP14-PY4-L-NP14-PY4
Figure BDA0000481033200000161
[HP-L-NP14-PY4-L-NP14-PY4]
[ HP-AN-NP14-PY4] (1 mmol,663 mg), [ HP-AN9B-NP14-PY4] (1 mmol,425 mg) and tetrakis (triphenylphosphine) palladium (25 mg) were mixed, and a mixed solution of toluene (2 ml)/ethanol (2ml)/2M Na2CO3(0.5ml) was added. The reaction was stirred at 100 ℃ for 4 hours and then cooled to room temperature. The reaction was diluted with water (40 ml) and extracted with ethyl acetate (3 x 40 ml). The organic phase was dried over anhydrous magnesium sulfate, concentrated and subjected to silica gel column chromatography to give HP-L-NP14-PY4-L-NP14-PY4 (675 mg, 70% yield) as a pale white solid.
The NMR data of the product is shown in figure 1.
Example 35
Preparation of the Compound HP-L-NP14-PY4-L-NP14-PY3
Figure BDA0000481033200000162
[HP-L-NP14-PY4-L-NP14-PY3]
The same reaction as in example 34 was carried out except that HP-AN9B-NP14-PY3 was used in place of HP-AN9B-NP14-PY4 to give HP-L-NP14-PY4-L-NP14-PY 3.
MS(EI)m/z=963.36(M+)
Example 36
Preparation of the Compound HP-L-PH44-PY4-L-PH44-PY4
Figure BDA0000481033200000171
[HP-L-PH44-PY4-L-PH44-PY4]
The same reaction as in example 34 was carried out except that HP-AN-PH44-PY4 was used instead of HP-AN-NP14-PY4 and HP-AN9B-PH44-PY4 was used instead of HP-AN9B-NP14-PY4 to obtain HP-L-PH44-PY4-L-PH44-PY 4.
The NMR data of the product is shown in figure 2.
Example 37
Preparation of the Compound HP-L-PH44-PY4-L-PH44-PY3
Figure BDA0000481033200000172
[HP-L-PH44-PY4-L-PH44-PY3]
The same reaction as in example 34 was carried out except that HP-AN-PH44-PY4 was used instead of HP-AN-NP14-PY4 and HP-AN9B-PH44-PY3 was used instead of HP-AN9B-NP14-PY4 to obtain HP-L-PH44-PY4-L-PH44-PY 3.
The NMR data of the product is shown in figure 3.
Spectral data of the product is shown in fig. 9.
Example 38
Preparation of the Compound HP-L-PH44-PY4-L-PH44-PY2
Figure BDA0000481033200000173
[HP-L-PH44-PY4-L-PH44-PY2]
The same reaction as in example 34 was carried out except that HP-AN-PH44-PY4 was used instead of HP-AN-NP14-PY4 and HP-AN9B-PH44-PY2 was used instead of HP-AN9B-NP14-PY4 to obtain HP-L-PH44-PY4-L-PH44-PY 2.
The NMR data of the product is shown in figure 4.
Example 39
Preparation of the Compound HP-L-PH44-PY3-L-PH44-PY2
Figure BDA0000481033200000181
[HP-L-PH44-PY3-L-PH44-PY2]
The same reaction as in example 34 was carried out except that HP-AN-PH44-PY3 was used instead of HP-AN-NP14-PY4 and HP-AN9B-PH44-PY2 was used instead of HP-AN9B-NP14-PY4 to obtain HP-L-PH44-PY3-L-PH44-PY 2.
MS(EI)m/z=813.31(M+)
Example 40
Preparation of the Compound HP-L-PH44-PY2-L-PH44-PY3
Figure BDA0000481033200000182
[HP-L-PH44-PY2-L-PH44-PY3]
The same reaction as in example 34 was carried out except that HP-AN-PH44-PY2 was used instead of HP-AN-NP14-PY4 and HP-AN9B-PH44-PY3 was used instead of HP-AN9B-NP14-PY4 to obtain HP-L-PH44-PY2-L-PH44-PY 3.
MS(EI)m/z=813.31(M+)
EXAMPLE 41
Preparation of the Compound HP-L-PH44-PY3-L-PH44-PY3
Figure BDA0000481033200000183
[HP-L-PH44-PY3-L-PH44-PY3]
The same reaction as in example 34 was carried out except that HP-AN-PH44-PY3 was used instead of HP-AN-NP14-PY4 and HP-AN9B-PH44-PY3 was used instead of HP-AN9B-NP14-PY4 to obtain HP-L-PH44-PY3-L-PH44-PY 3.
MS(EI)m/z=813.31(M+)
Example 42
Preparation of the Compound HP-L-PH44-PY2-L-2PH44-PY4
Figure BDA0000481033200000191
[HP-L-PH44-PY2-L-2PH44-PY4]
The same reaction as in example 34 was carried out except that HP-AN-PH44-PY2 was used instead of HP-AN-NP14-PY4 and HP-AN9B-2PH44-PY4 was used instead of HP-AN9B-NP14-PY4 to obtain HP-L-PH44-PY2-L-2PH44-PY 4.
The NMR data of the product is shown in figure 5.
Example 43
Preparation of the Compound HP-L-PH44-PY4-L-NP14-PY2
Figure BDA0000481033200000192
[HP-L-PH44-PY4-L-NP14-PY2]
The same reaction as in example 34 was carried out except that HP-AN-PH44-PY4 was used instead of HP-AN-NP14-PY4 and HP-AN9B-NP14-PY2 was used instead of HP-AN9B-NP14-PY4 to obtain HP-L-PH44-PY4-L-NP14-PY 2.
MS(EI)m/z=866.33(M+)
Example 44
Preparation of the Compound HP-L-2PH44-PY4-L-2PH44-PY4
Figure BDA0000481033200000201
[HP-L-2PH44-PY4-L-2PH44-PY4]
The same reaction as in example 34 was carried out except that HP-AN-2PH44-PY4 was used instead of HP-AN-NP14-PY4 and HP-AN9B-2PH44-PY4 was used instead of HP-AN9B-NP14-PY4 to obtain the compound HP-L-2PH44-PY4-L-2PH44-PY 4.
The NMR data of the product is shown in figure 6.
Example 45
Preparation of the Compound HP-L-2PH44-PY4-L-PH44-PY4
Figure BDA0000481033200000202
[HP-L-2PH44-PY4-L-PH44-PY4]
The same reaction as in example 34 was carried out except that HP-AN-2PH44-PY4 was used instead of HP-AN-NP14-PY4 and HP-AN9B-PH44-PY4 was used instead of HP-AN9B-NP14-PY4 to obtain the compound HP-L-2PH44-PY4-L-PH44-PY 4.
MS(EI)m/z=965.38(M+)
Example 46
Preparation of the Compound HP-L1-PH44-PY3-L-PH44-PY4
Figure BDA0000481033200000211
[HP-L1-PH44-PY3-L-PH44-PY4]
The same reaction as in example 34 was carried out except that HP-ANme-PH44-PY3 was used instead of HP-AN 14-PY4 and HP-AN9B-PH44-PY4 was used instead of HP-AN9B-NP14-PY4, whereby the compound HP-L1-PH44-PY3-L-PH44-PY4 was obtained.
The NMR data of the product is shown in figure 7.
Example 47
Preparation of the Compound HP-L2-PH44-PY4-L-PH44-PY4
Figure BDA0000481033200000212
[HP-L2-PH44-PY4-L-PH44-PY4]
The same reaction as in example 34 was carried out except that HP-ANet-PH44-PY4 was used instead of HP-AN 14-PY4 and HP-AN9B-PH44-PY4 was used instead of HP-AN9B-NP14-PY4, whereby the compound HP-L2-PH44-PY4-L-PH44-PY4 was obtained.
The NMR data of the product is shown in figure 8.
Example 48
Preparation of the Compound HP-L2-PH44-PY4-L-PH44-PY3
Figure BDA0000481033200000213
[HP-L2-PH44-PY4-L-PH44-PY3]
The same reaction as in example 34 was carried out except that HP-ANet-PH44-PY4 was used instead of HP-AN 14-PY4 and HP-AN9B-PH44-PY3 was used instead of HP-AN9B-NP14-PY4, whereby the compound HP-L2-PH44-PY4-L-PH44-PY3 was obtained.
MS(EI)m/z=841.35(M+)
Example 49
Preparation of the Compound HP-L2-PH44-PY4-L-PH44-PY3
Figure BDA0000481033200000221
[HP-L2-PH44-PY4-L-PH44-PY3]
The same reaction as in example 34 was carried out except that HP-ANet-PH44-PY4 was used instead of HP-AN 14-PY4 and HP-AN9B-PH44-PY3 was used instead of HP-AN9B-NP14-PY4, whereby the compound HP-L2-PH44-PY4-L-PH44-PY3 was obtained.
MS(EI)m/z=993.41(M+)
Example 50
Acquisition of electronic recombination energy of the Compound HP-L-NP14-PY4-L-NP14-PY4 obtained in example 34
Inputting the molecular coordinates of the compound HP-L-NP14-PY4-L-NP14-PY4 into quantum chemical software, optimizing under b3lyp/6-31G (d, p), respectively obtaining the ground state energy (E1) of the compound, the vertical excited state energy (E2) containing one electron, the adiabatic excited state energy (E3) containing one electron, and obtaining the electronic recombination energy E of the compound by a recombination energy calculation formula E = | E1-E4| + | E2-E3| based on the neutral molecular energy (E4) of the adiabatic excited state configuration.
Example 51
Acquisition of Electron recombination energy of the Compound HP-L-PH44-PY2-L-2PH44-PY4 obtained in example 42
The same operation as in example 50 was carried out except that the molecular coordinates of the compound HP-L-PH44-PY2-L-2PH44-PY4 were used in place of the molecular coordinates of HP-L-NP14-PY4-L-NP14-PY4 to obtain the compound [ HP-L-PH44-PY2-L-2PH44-PY4] as an electron recombination energy.
Example 52
Acquisition of Electron recombination energy of the Compound HP-L2-PH44-PY4-L-PH44-PY4 obtained in example 47
The same procedures used in example 50 were repeated except for replacing HP-L-NP14-PY4-L-NP14-PY4 with the molecular coordinates of the compound HP-L2-PH44-PY4-L-PH44-PY4 to obtain the compound [ HP-L2-PH44-PY4-L-PH44-PY4] as an electron recombination energy.
Comparative example
Acquisition of Compound AND Electron recombination energy
By the same operation as in example 50 except that the molecular coordinates of HP-L-NP14-PY4-L-NP14-PY4 were replaced with those of AND,
AND obtaining the compound AND electron recombination energy.
Figure BDA0000481033200000231
The electron recombination energy data obtained above are shown in the following table:
E1(a.u.) E2（a.u.） E3（a.u.） E4（a.u.） E（a.u.） relative mobility
Example 50 2512.3565397 2512.3909196 2512.3987687 2512.3510566 0.01333 1.03
Example 51 2512.3559116 2512.3900936 2512.3968187 2512.3499391 0.0127 1.06
Example 52 2512.3555262 2512.3878386 2512.3951449 2512.3498831 0.01295 1.05
Comparative example 1308.9535859 1308.9672428 1308.9751160 1308.9472085 0.01425 1
According to the literature (J.Phys.chem.A2003, 107, 5241-5251), the smaller the recombination energy, the higher the electron mobility. From the above table, it can be seen that the examples perform well in electron recombination compared with the conventional AND, indicating that the compound of the present invention can also be applied in the field of electroluminescence as an electron transport material.
Although the invention has been described in connection with the embodiments, the invention is not limited to the embodiments described above, and it should be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the invention, and the scope of the invention is outlined by the appended claims.

Claims (1)

1. A method for preparing dianthracene compounds shown as a general formula I,
Figure FDF0000009834740000011
the method comprises the following steps:
1) reacting a compound of formula 2
Figure FDF0000009834740000012
And a compound of formula 9
Figure FDF0000009834740000013
Obtaining the compound of formula 10 by coupling reaction
Figure FDF0000009834740000014
Obtaining the compound of formula 11 by bromination
Figure FDF0000009834740000021
2) The compounds of formula 11 and 12
Figure FDF0000009834740000022
Obtaining the compound of formula 13 by a coupling reaction
Figure FDF0000009834740000023
Bromination to give the compound of formula 14
Figure FDF0000009834740000024
3) The compounds of formula 14 and formula 15
Figure FDF0000009834740000025
Through coupling reaction, the dianthracene compound shown in the general formula I is obtained
Figure FDF0000009834740000026
Wherein the content of the first and second substances,
L1and L2The same or different, independently of each other, represent a substituted or unsubstituted heterocyclic aromatic group of C2-C60 or a substituted or unsubstituted hydrocarbon aromatic group of C6-C60;
L3independently represent a substituted or unsubstituted heterocyclic aromatic group of C2-C60 or a substituted or unsubstituted hydrocarbon aromatic group of C6-C60;
provided that L is1、L2And L3Is not simultaneously
Figure FDF0000009834740000031
R11、R12、R13、R14、R15、R16、R17、R18、R21、R23、R24、R25、R26、R27And R28Identical or different, independently of one another, represent hydrogen, halogen, C1-C10 substituted or unsubstitutedSubstituted alkyl, or substituted or unsubstituted alkoxy of C1-C10;
X4is halogen.
CN201410111568.0A 2013-12-27 2014-03-24 Dianthracene compound with pyridyl at tail end and application thereof Active CN104744347B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201410111568.0A CN104744347B (en) 2013-12-27 2014-03-24 Dianthracene compound with pyridyl at tail end and application thereof

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CN2013107391317 2013-12-27
CN201310739131 2013-12-27
CN201410111568.0A CN104744347B (en) 2013-12-27 2014-03-24 Dianthracene compound with pyridyl at tail end and application thereof

Publications (2)

Publication Number Publication Date
CN104744347A CN104744347A (en) 2015-07-01
CN104744347B true CN104744347B (en) 2021-03-02

Family

ID=53584700

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201410111568.0A Active CN104744347B (en) 2013-12-27 2014-03-24 Dianthracene compound with pyridyl at tail end and application thereof

Country Status (1)

Country Link
CN (1) CN104744347B (en)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5935721A (en) * 1998-03-20 1999-08-10 Eastman Kodak Company Organic electroluminescent elements for stable electroluminescent
CN101395105A (en) * 2006-03-06 2009-03-25 Lg化学株式会社 Novel anthracene derivative and organic electronic device using the same
CN101967079A (en) * 2009-07-28 2011-02-09 靳焕改 Organic material and application thereof to organic electroluminescent devices
CN102742042A (en) * 2010-01-29 2012-10-17 住友化学株式会社 Luminescent composition and light-emitting element using said composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5935721A (en) * 1998-03-20 1999-08-10 Eastman Kodak Company Organic electroluminescent elements for stable electroluminescent
CN101395105A (en) * 2006-03-06 2009-03-25 Lg化学株式会社 Novel anthracene derivative and organic electronic device using the same
CN101967079A (en) * 2009-07-28 2011-02-09 靳焕改 Organic material and application thereof to organic electroluminescent devices
CN102742042A (en) * 2010-01-29 2012-10-17 住友化学株式会社 Luminescent composition and light-emitting element using said composition

Also Published As

Publication number Publication date
CN104744347A (en) 2015-07-01

Similar Documents

Publication Publication Date Title
Xiao et al. Highly efficient hybridized local and Charge-transfer (HLCT) Deep-blue electroluminescence with excellent molecular horizontal orientation
TWI495625B (en) Organic electroluminescent devices
US20060226768A1 (en) Silicon-contained anthracene compound for organic electroluminescent device
CN109593097A (en) A kind of phosphorescence host compound and its organic electroluminescence device using the compound
CN110563746B (en) Novel SO2 spiro-structure-containing compound and application thereof in OLED (organic light emitting diode) device
WO2018120970A1 (en) Green light dye with aggregation-induced emission property
WO2018014406A1 (en) Light-emitting material, preparation method therefor, organic light-emitting diode using the light-emitting material
Ye et al. Imidazole derivatives for efficient organic light-emitting diodes
CN111793063A (en) Organic light-emitting molecules and application thereof in organic light-emitting diode
TW201632488A (en) Organic electroluminescent device
TW201632489A (en) Organic electroluminescent device
WO2018014403A1 (en) Light-emitting material and method for fabrication thereof, and organic light-emitting diode using said light-emitting material
CN111320615B (en) Small molecules based on S, S-dioxo-dibenzothiophene and phenanthroimidazole and application thereof in electroluminescent device
WO2021120450A1 (en) Thermally-activated delayed fluorescence green light polymer material and preparation method therefor
WO2018120968A1 (en) Light conversion film containing green light dye having aggregation-induced emission property
CN115850187B (en) Organic electroluminescent material based on dibenzo-xenoimidazole derivative, preparation method and application thereof
CN104744346B (en) Dianthracene compound with pyridyl at tail end and application thereof
WO2018014388A1 (en) Light-emitting material, preparation method therefor, and organic light-emitting diode made of light-emitting material
WO2016138710A1 (en) Metal complex and manufacturing method and usage, display device thereof
KR20150030300A (en) Fluorescent compound and Organic light emitting diode device using the same
TWI510482B (en) Biphenyl derivative and organic electroluminescent device
CN104744347B (en) Dianthracene compound with pyridyl at tail end and application thereof
Li et al. Expanded benzofuran-decorated twistacene derivatives: synthesis, characterization and single-component white electroluminescence
JP2012144523A (en) 1, 2, 4, 5-substituted phenyl derivative, production method for the same and organic electroluminescent element
CN106187966B (en) A kind of electroluminescent organic material, preparation method and applications

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant