CN106349106A - Organic photoelectric material and organic electrofluorescence device including material - Google Patents

Organic photoelectric material and organic electrofluorescence device including material Download PDF

Info

Publication number
CN106349106A
CN106349106A CN201610711611.6A CN201610711611A CN106349106A CN 106349106 A CN106349106 A CN 106349106A CN 201610711611 A CN201610711611 A CN 201610711611A CN 106349106 A CN106349106 A CN 106349106A
Authority
CN
China
Prior art keywords
organic
layer
compound
luminescent
electroluminescence device
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.)
Granted
Application number
CN201610711611.6A
Other languages
Chinese (zh)
Other versions
CN106349106B (en
Inventor
高自良
张成新
冯鑫
石宇
王元贵
王新涛
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.)
Valiant Co Ltd
Original Assignee
Valiant 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 Valiant Co Ltd filed Critical Valiant Co Ltd
Priority to CN201610711611.6A priority Critical patent/CN106349106B/en
Publication of CN106349106A publication Critical patent/CN106349106A/en
Application granted granted Critical
Publication of CN106349106B publication Critical patent/CN106349106B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/34—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by unsaturated carbon chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • 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
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • 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
    • H10K85/657—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
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • 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)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The invention relates to an organic photoelectric material, which is characterized in that by using an anthraquinone ring as the center, aryls are introduced into the site 2 and the site 6 of the anthraquinone ring; the general molecular formula of the organic photoelectric material is shown as the formula (I) shown as the accompanying drawing, wherein the Ar1 and Ar2 are independently substituent groups containing substituent groups or containing no substituent group. The invention also relates to a preparation method of the organic photoelectric material. The invention also relates to an organic electrofluorescence device using the organic photoelectric material in a luminous layer. The luminous layer is prepared from the organic photoelectric material and BEP, so that the turn-on voltage and the maximum brightness of a prepared OLED (organic light emitting diode) luminous device can be greatly improved; a good application effect is achieved; good industrialization products are realized.

Description

A kind of organic photoelectrical material and the organic electroluminescence device comprising this material
Technical field
The present invention relates to material science, more specifically it relates to a kind of organic photoelectrical material and comprise this material Organic electroluminescence device.
Background technology
Organic electroluminescent diode (oled) results from the eighties in last century, and organic light emitting diode (oled) has certainly Luminous, wide viewing angle, fast response time, many advantages, such as can achieve Flexible Displays, through the development of more than two decades, this technology by Step moves to maturity, at present, organic electroluminescent technology, be mainly used in two fields, respectively full-color display and white light Illumination, based on the commodity of oled Display Technique, has been done step-by-step industrialization, such as, in commodity such as smart mobile phone, curved surface TVs In, applied this technology widely.
In order to realize full-color display, it is respectively necessary for the luminescent device of three kinds of colors of red, green, blue, with red device and green glow Device is compared, and blue luminescent device is still not mature enough, and device lifetime and efficiency are low.People pass through ultra clean technology, encapsulate skill Art, exploitation has blue light material of high glass-transition temperature etc. to improve the life-span of blue-light device, and doping techniques and exploitation There is the new material of the two poles of the earth structure, be then the direction improving device efficiency.
Doping techniques are by luminescent material (guest materials) being dispersed among other materials (material of main part), to reduce The concentration of luminescent material, thus avoiding intermolecular aggregation and concentration quenching, and then realizing improving device efficiency, improving electroluminescent Excitation, extends the purpose of device lifetime.
Content of the invention
For solving above technical problem, the invention provides a kind of organic photoelectrical material, its centered on anthraquinone ring, and 2 of described anthraquinone ring and 6 introducing aryl, shown in the general structure such as formula (i) of described organic photoelectrical material:
Wherein, ar1And ar2It independently is the aryl containing substituent group or without substituent group.
Preferably, described ar1And ar2Molecular weight independently between 60-500.
Preferably, described ar1And ar2Independently selected from the phenyl containing substituent group or without substituent group, naphthyl, phenanthryl, anthracene Base, fluoranthene base, fluorenyl, pyrenyl, triphenylenyl, dibenzofuran group, dibenzothiophenes base, carbazyl, n- substituted carbazole base.
Preferably, the structural formula of described organic photoelectrical material is:
Present invention also offers a kind of preparation method of above-mentioned organic photoelectrical material, comprise the following steps:
1) based on 2,6- dibromo-anthraquinone, synthetic intermediate 1, reaction equation is as follows:
2) synthesize compound 1 with described intermediate 1, reaction equation is as follows:
3) with described compound 1 as raw material, the aromatic compounds replacing with boronate carry out pitching coupling reaction, obtain described Luminous organic material.
Present invention also offers a kind of organic electroluminescence device, it includes luminescent layer, and described luminescent layer is by above-mentioned luminous Material and bep composition.
Preferably, described luminescent material and the mass ratio of described bep are 9:1.
Preferably, described organic electroluminescence device is passed by ito Conducting Glass, hole transmission layer, luminescent layer, electronics Defeated layer, electron injecting layer and cathode layer stack gradually and form.Wherein, hole transmission layer is made up of npb, and electron transfer layer is by tpbi Make, electron injecting layer is made up of lithium fluoride, cathode layer is made of aluminum.
Brief description
Fig. 1 is the Rotating fields schematic diagram of the electroluminescent device of the present invention.
101st, ito Conducting Glass, 102, hole transmission layer, 103, luminescent layer, 104, electron transfer layer, 105, electronics Implanted layer, 106 cathode layers.
Specific embodiment
Below in conjunction with accompanying drawing and example, the principle of the present invention and feature are described, example is served only for explaining this Bright, it is not intended to limit the scope of the present invention.
COMPOUNDS EXAMPLE
1. the preparation of compound 1:
1) prepare intermediate 1
Addition 2,6- dibromo-anthraquinone (73.2g, 0.20mol) in 1l there-necked flask, ethylene glycol (14.9g, 0.24mol), 2.5g p-methyl benzenesulfonic acid, 400ml dimethylbenzene, it is heated to reflux, fraction water device water-dividing flows back 12 hours.After reaction terminates, wash, divide Liquid, organic faciess removed under reduced pressure solvent, column chromatography, toluene pet ether recrystallization, obtain white solid intermediate 1, hplc purity 99.6%, yield 68.63%, ms (m/s): 407.9.
2) prepare compound 1
The preparation of intermediate 2: in the 1l there-necked flask being furnished with constant pressure funnel, addition magnesium metal (5.1g, 0.21mol), bromobenzene (31.4g, 0.20mol) is dissolved in 200g oxolane, is placed in constant pressure funnel, use Nitrogen is protected, and heating there-necked flask reaches 65 DEG C to temperature in bottle, adds the oxolane to bromo-iodobenzene by constant pressure funnel Solution, is firstly added 50ml, after question response causes, slowly instills remainder, 1h completion of dropping, reacts 2h under reflux temperature, It is transferred to stand-by in constant pressure funnel after being down to room temperature.Intermediate 1 (82.0g, 0.20mol) is dissolved among 200g oxolane It is added in 2l there-necked flask, is then slowly added dropwise above-mentioned stand-by solution, react 3h under reflux temperature, after reaction terminates, be cooled to 25 DEG C, above reactant liquor is slowly poured in the dilute hydrochloric acid that 200g mass concentration is 10%, stirs 15min, point liquid, collect organic Phase, solvent is sloughed in decompression, obtains thick liquid, is not refined, and is directly used in next step reaction.
Add 250g benzene in above-mentioned gained thick liquid, stirring is lower to add 1.42g (0.01mol) boron trifluoride diethyl etherate molten Liquid, 60～65 DEG C of reaction 4h, reaction, removed under reduced pressure solvent are quenched, column chromatography obtains intermediate 2, hplc purity 99.6%, yield 45.88%, ms (m/s): 546.0.
The preparation of intermediate 3: collect above intermediate 2 (54.8g, 0.1mol), add 250ml toluene and 50ml 85% Formic acid, be warming up to backflow, insulation reaction 10 hours.Divide liquid, washing, organic faciess removed under reduced pressure solvent, column chromatography, obtain white Solid is intermediate 3, hplc purity 99.6%, yield 85.22%, ms (m/s): 502.0.
The preparation of compound 1: in 1l there-necked flask, under nitrogen protection, add intermediate 3 (40.3g, 0.08mol), the third two Nitrile (6.6g, 0.10mol), 500ml anhydrous methylene chloride, ice bath is cooled to interior temperature 0-5 DEG C, slowly instills 22ml (0.20mol) Titanium tetrachloride, about 0.5 hour completion of dropping, it is slowly dropped into 70ml pyridine, about 1.0 hours completion of dropping, completion of dropping removes ice Bath, the lower room temperature 20-25 DEG C stirring reaction of nitrogen protection 24 hours.It is 10% that above reactant liquor is slowly poured into 300g mass concentration Dilute hydrochloric acid in, stir 10min, point liquid, collect organic faciess, decompression is sloughed solvent, obtained yellow solid, after glacial acetic acid recrystallization The yellow solid obtaining is compound 1, hplc purity 99.5%, yield 73.58%.
High resolution mass spectrum, esi source, positive ion mode, molecular formula c29h16br2n2, theoretical value 549.9680, test value, 549.9683.Elementary analysiss (c29h16br2n2), theoretical value c:63.07, h:2.92, n:5.07, measured value c:63.08, h: 2.94, n:5.05.
The preparation of embodiment 1 compound c01
In 250ml there-necked flask, addition compound 1 (2.76g, 0.005mol), phenylboric acid (1.34g, 0.011mol), k2co3(2.07g, 0.015mol), toluene (60ml), deionized water (20ml), n2Protection, adds pd (pph3)4(17 5mg), rises Temperature, to flowing back, is reacted 10 hours, stops reacting, cooling, point liquid, 50ml deionization is washed 1 time, collects organic faciess, slough solvent, institute Obtain crude product and use silica gel column chromatography purification, obtain object c01, hplc purity 99.8%, yield 84.55%.
High resolution mass spectrum, esi source, positive ion mode, molecular formula c41h26n2, theoretical value 546.2096, test value 546.2092.Elementary analysiss (c41h26n2), theoretical value c:90.08, h:4.80, n:5.12, measured value c:90.05, h:4.82, N:5.13.
The preparation of embodiment 2 compound c02
With embodiment 1, difference is using raw material 1- naphthalene boronic acids alternative embodiment 1 preparation method of compound c02 In phenylboric acid.
High resolution mass spectrum, esi source, positive ion mode, molecular formula c49h30n2, theoretical value 646.2409, test value 646.2403.Elementary analysiss (c49h30n2), theoretical value c:90.99, h:4.68, n:4.33, measured value c:90.96, h:4.67, N:4.37.
The preparation of embodiment 3 compound c04
With embodiment 1, difference is using raw material 4- biphenylboronic acid alternative embodiment the preparation method of compound c04 Phenylboric acid in 1.
High resolution mass spectrum, esi source, positive ion mode, molecular formula c53h34n2, theoretical value 698.2722, test value 698.2726.Elementary analysiss (c53h34n2), theoretical value c:91.09, h:4.90, n:4.01, measured value c:91.11, h:4.88, N:4.01.
The preparation of embodiment 4 compound c07
With embodiment 1, difference is using raw material 9- phenanthrene boric acid alternative embodiment 1 preparation method of compound c07 In phenylboric acid.
High resolution mass spectrum, esi source, positive ion mode, molecular formula c57h34n2, theoretical value 746.2722, test value 746.2725.Elementary analysiss (c57h34n2), theoretical value c:91.66, h:4.59, n:3.75, measured value c:91.68, h:4.58, N:3.74.
The preparation of embodiment 5 compound c08
With embodiment 1, difference is using raw material 9- anthracene boric acid alternative embodiment 1 preparation method of compound c08 In phenylboric acid.
High resolution mass spectrum, esi source, positive ion mode, molecular formula c57h34n2, theoretical value 746.2722, test value 746.2728.Elementary analysiss (c57h34n2), theoretical value c:91.66, h:4.59, n:3.75, measured value c:91.67, h:4.57, N:3.76.
The preparation of embodiment 6 compound c09
With embodiment 1, difference is to replace using raw material 10- phenylanthracene -9- boric acid the preparation method of compound c09 Phenylboric acid in embodiment 1.
High resolution mass spectrum, esi source, positive ion mode, molecular formula c69h42n2, theoretical value 898.3348, test value 898.3345.Elementary analysiss (c69h42n2), theoretical value c:92.18, h:4.71, n:3.11, measured value c:92.16, h:4.73, N:3.11.
The preparation of embodiment 7 compound c10
With embodiment 1, difference is to be replaced using raw material fluoranthene -3- boric acid and implements the preparation method of compound c10 Phenylboric acid in example 1.
High resolution mass spectrum, esi source, positive ion mode, molecular formula c61h34n2, theoretical value 794.2722, test value 794.2723.Elementary analysiss (c61h34n2), theoretical value c:92.16, h:4.32, n:3.52, measured value c:92.14, h:4.33, N:3.53.
The preparation of embodiment 8 compound c12
With embodiment 1, difference is using raw material 9,9- dimethyl fluorene -2- boric acid the preparation method of compound c12 Phenylboric acid in alternative embodiment 1.
High resolution mass spectrum, esi source, positive ion mode, molecular formula c59h42n2, theoretical value 778.3348, test value 778.3345.Elementary analysiss (c59h42n2), theoretical value c:90.97, h:5.43, n:3.60, measured value c:90.94, h:5.41, N:3.65.
The preparation of embodiment 9 compound c13
With embodiment 1, difference is using raw material pyrene -1- boric acid alternative embodiment 1 preparation method of compound c13 In phenylboric acid.
High resolution mass spectrum, esi source, positive ion mode, molecular formula c61h38n2, theoretical value 798.3035, test value 798.3039.Elementary analysiss (c61h38n2), theoretical value c:91.70, h:4.79, n:3.51, measured value c:91.73, h:4.78, N:3.49.
The preparation of embodiment 10 compound c14
With embodiment 1, difference is to replace in fact using raw material triphenylene -2- boric acid the preparation method of compound c14 Apply the phenylboric acid in example 1.
High resolution mass spectrum, esi source, positive ion mode, molecular formula c65h38n2, theoretical value 846.3035, test value 846.3039.Elementary analysiss (c65h38n2), theoretical value c:92.17, h:4.52, n:3.31, measured value c:92.14, h:4.54, N:3.32.
The preparation of embodiment 11 compound c17
With embodiment 1, difference is to replace using raw material dibenzofurans -4- boric acid the preparation method of compound c17 Change the phenylboric acid in embodiment 1.
High resolution mass spectrum, esi source, positive ion mode, molecular formula c53h30n2o2, theoretical value 726.2307, test value 726.2310.Elementary analysiss (c53h30n2o2), theoretical value c:87.58, h:4.16, n:3.85, o:4.40, measured value c: 87.55, h:4.18, n:3.88, o:4.39.
The preparation of embodiment 12 compound c19
With embodiment 1, difference is to replace using raw material n- phenyl carbazole -3- boric acid the preparation method of compound c19 Change the phenylboric acid in embodiment 1.
High resolution mass spectrum, esi source, positive ion mode, molecular formula c65h40n4, theoretical value 876.3253, test value 876.3257.Elementary analysiss (c65h40n4), theoretical value c:89.01, h:4.60, n:6.39, measured value c:89.05, h:4.57, N:6.38.
Device embodiments
The present invention chooses compound c02, compound c04, compound c07, compound c08, compound c09, compound C10, compound c12, compound c13, compound c14, compound c17, compound c19 make organic electroluminescence device, by This is prepared for the organic electroluminescence device of embodiment 13-23 respectively.
All embodiments all prepare blue organic electroluminescent device by the following method:
A) cleaning ito (tin indium oxide) glass substrate (101): deionized water, acetone, EtOH Sonicate cleaning ito respectively Each 30 minutes of glass, is then processed 5 minutes in plasma cleaner；
B) in upper vacuum evaporation hole transmission layer (102) npb of anode ito glass substrate (101), thickness is 50nm；
C) on hole transmission layer npb, vacuum mixing evaporation as luminescent layer (103) one of above-claimed cpd and The mass ratio 9:1 of bep, described compound and bep, thickness is 30nm；
D) on luminescent layer (103), as the tpbi of electron transfer layer (104), thickness is 30nm for vacuum evaporation；
E) on electric transmission (104) layer tpbi, vacuum evaporation electron injecting layer (105) lif, thickness is 1nm；
F) on electron injecting layer (105) lif, vacuum evaporation negative electrode (106) al, thickness is 100nm.
The structure of device is ito/npb (50nm)/described compound: bep=9:1, (w/w, 30nm)/tpbi (30nm)/ lif(1nm)/al(100nm).
All device embodiments of the present invention are identical with the processing technology of comparative example, and employed identical base Panel material and electrode material, the thickness of electrode material is also consistent, except that the main body material to the luminescent layer in device Material converts.The composition structure of each device is as shown in table 1.The test result of device is shown in Table 2.
Table 1 device architecture
Table 2 device detection result
The result of table 2 can be seen that compound of the present invention can apply and oled luminescent device make, and with compare Example is compared, and either opens bright voltage or high-high brightness all obtains larger change than known oled material.Material of the present invention There is in oled luminescent device good application effect, there is good industrialization prospect.
The foregoing is only presently preferred embodiments of the present invention, not in order to limit the present invention, all spirit in the present invention and Within principle, any modification, equivalent substitution and improvement made etc., should be included within the scope of the present invention.

Claims (9)

1. a kind of organic photoelectrical material is it is characterised in that centered on anthraquinone ring, and 2 in anthraquinone ring and 6 introduce virtue Base, shown in the general structure such as formula (i) of described organic photoelectrical material:
Wherein, ar1And ar2It independently is the aryl containing substituent group or without substituent group.
2. organic photoelectrical material according to claim 1 is it is characterised in that described ar1And ar2Molecular weight independently exist Between 60-500.
3. organic photoelectrical material according to claim 2 is it is characterised in that described ar1And ar2Take independently selected from containing For base or without the phenyl of substituent group, naphthyl, phenanthryl, anthryl, fluoranthene base, fluorenyl, pyrenyl, triphenylenyl, dibenzofuran group, Dibenzothiophenes base, carbazyl, n- substituted carbazole base.
4. organic photoelectrical material according to claim 1 is it is characterised in that the structural formula of described organic photoelectrical material is:
5. the preparation method of the organic photoelectrical material any one of claim 1-4 is it is characterised in that include following walking Rapid:
1) based on 2,6- dibromo-anthraquinone, synthetic intermediate 1, reaction equation is as follows:
2) synthesize compound 1 with described intermediate 1, reaction equation is as follows:
3) with described compound 1 as raw material, the aromatic compounds replacing with boronate carry out pitching coupling reaction, obtain described organic Luminescent material.
6. a kind of organic electroluminescence device, including luminescent layer it is characterised in that described luminescent layer is appointed by claim 1-4 Luminescent material described in one and bep composition.
7. organic electroluminescence device according to claim 6 is it is characterised in that described luminescent material is with described bep's Mass ratio is 9:1.
8. organic electroluminescence device according to claim 6 it is characterised in that described organic electroluminescence device by Ito Conducting Glass, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and cathode layer stack gradually and form.
9. organic electroluminescence device according to claim 8 is it is characterised in that described hole transmission layer is made up of npb, Described electron transfer layer is made up of tpbi, and described electron injecting layer is made up of lithium fluoride, and described cathode layer is made of aluminum.
CN201610711611.6A 2016-08-24 2016-08-24 A kind of organic photoelectrical material and the organic electroluminescence device comprising the material Active CN106349106B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610711611.6A CN106349106B (en) 2016-08-24 2016-08-24 A kind of organic photoelectrical material and the organic electroluminescence device comprising the material

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610711611.6A CN106349106B (en) 2016-08-24 2016-08-24 A kind of organic photoelectrical material and the organic electroluminescence device comprising the material

Publications (2)

Publication Number Publication Date
CN106349106A true CN106349106A (en) 2017-01-25
CN106349106B CN106349106B (en) 2018-01-30

Family

ID=57844718

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610711611.6A Active CN106349106B (en) 2016-08-24 2016-08-24 A kind of organic photoelectrical material and the organic electroluminescence device comprising the material

Country Status (1)

Country Link
CN (1) CN106349106B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107235858A (en) * 2017-07-13 2017-10-10 长春海谱润斯科技有限公司 A kind of electroluminescent organic material and its organic luminescent device with electric transmission effect

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0061264A1 (en) * 1981-03-13 1982-09-29 Matsushita Electric Industrial Co., Ltd. Tetracyanoanthraquinodimethane compounds and processes for the production thereof, polymers and charge-transfer complexes derived therefrom
US5102757A (en) * 1988-09-13 1992-04-07 Fuji Xerox Co., Ltd. Electrophotographic photosensitive member and image forming process
CN102786438A (en) * 2011-05-16 2012-11-21 海洋王照明科技股份有限公司 Cyano anthraquinone derivatives, preparation method and organic electroluminescent devices thereof
US20160216618A1 (en) * 2015-01-26 2016-07-28 Canon Kabushiki Kaisha Electrophotographic photosensitive member, manufacturing method of electrophotographic photosensitive member, process cartridge and electrophotographic apparatus

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0061264A1 (en) * 1981-03-13 1982-09-29 Matsushita Electric Industrial Co., Ltd. Tetracyanoanthraquinodimethane compounds and processes for the production thereof, polymers and charge-transfer complexes derived therefrom
US5102757A (en) * 1988-09-13 1992-04-07 Fuji Xerox Co., Ltd. Electrophotographic photosensitive member and image forming process
CN102786438A (en) * 2011-05-16 2012-11-21 海洋王照明科技股份有限公司 Cyano anthraquinone derivatives, preparation method and organic electroluminescent devices thereof
US20160216618A1 (en) * 2015-01-26 2016-07-28 Canon Kabushiki Kaisha Electrophotographic photosensitive member, manufacturing method of electrophotographic photosensitive member, process cartridge and electrophotographic apparatus

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
JIE LIU等: "Aggregation-induced emission enhancement based on 11,11,12,12,-tetracyano-9,10-anthraquinodimethane", 《CHEM.COMMUN》 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107235858A (en) * 2017-07-13 2017-10-10 长春海谱润斯科技有限公司 A kind of electroluminescent organic material and its organic luminescent device with electric transmission effect

Also Published As

Publication number Publication date
CN106349106B (en) 2018-01-30

Similar Documents

Publication Publication Date Title
CN104471021B (en) Novel organic electroluminescent element compound and organic electroluminescent element comprising same
CN105175313B (en) A kind of hole injection compound and its organic electroluminescence device
TW201038514A (en) Novel polymerizable monomer, and material for organic device, hole injection/transport material, material for organic electroluminescent element and organic electroluminescent element each comprising polymer (polymeric compound) of the polymerizable
Liu et al. Highly efficient nondoped blue organic light-emitting diodes with high brightness and negligible efficiency roll-off based on anthracene-triazine derivatives
Park et al. Synthesis and properties of blue-light-emitting anthracene derivative with diphenylamino-fluorene
US20110133632A1 (en) Deuterated compound as part of a combination of compounds for electronic applications
US11485905B2 (en) Green light thermally activated delayed fluorescent material and synthesizing method thereof, and electroluminescent device
CN105131938B (en) A kind of electroluminescent organic material and its application
CN107827807A (en) A kind of derivative containing carbazole structure and preparation method thereof and organic electroluminescence device
Huang et al. Unsymmetrically amorphous 9, 10-disubstituted anthracene derivatives for high-efficiency blue organic electroluminescence devices
CN109956965B (en) Compound, organic light-emitting display panel, and display device
JP2013515011A (en) Deuterated zirconium compounds for electronic applications
CN108047244A (en) A kind of snail compound and application thereof and organic electroluminescence device
CN105131939B (en) Organic electroluminescence material with spiral structure and application thereof
CN113861143B (en) Thermal-activation delayed fluorescence deep blue light material, preparation method thereof and organic electroluminescent device
CN109020979A (en) A kind of electroluminescent organic material and preparation method and application with heterocycle structure
CN106349106B (en) A kind of organic photoelectrical material and the organic electroluminescence device comprising the material
CN107652221A (en) A kind of derivative containing benzo carbazole structure and preparation method thereof and organic electroluminescence device
CN107936947A (en) A kind of spirane structure organic electroluminescent compositions and preparation method thereof
WO2020237885A1 (en) Dark blue thermal activation delayed fluorescent material and preparation method therefor, and electroluminescent device
CN103626792A (en) Arylboron-containing indolo[3,2-b]carbazole compound, and preparation and application thereof
CN108203420A (en) Derivative of naphthalene benzofuran and anthracene and preparation method thereof, application and device
CN106544009B (en) A kind of electroluminescent organic material with dibenzofuran structure and preparation method thereof and its application
CN109836421B (en) A compound of general formula and its application
Zhang et al. Novel carbazole dendronized oligofluorenes for solution-processed organic light-emitting diodes

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
PE01 Entry into force of the registration of the contract for pledge of patent right

Denomination of invention: The invention relates to an organic photoelectric material and an organic electroluminescent device containing the material

Effective date of registration: 20211202

Granted publication date: 20180130

Pledgee: Yantai Branch of China Merchants Bank Co.,Ltd.

Pledgor: VALIANT Co.,Ltd.

Registration number: Y2021980013807

PE01 Entry into force of the registration of the contract for pledge of patent right
PC01 Cancellation of the registration of the contract for pledge of patent right

Date of cancellation: 20220823

Granted publication date: 20180130

Pledgee: Yantai Branch of China Merchants Bank Co.,Ltd.

Pledgor: VALIANT Co.,Ltd.

Registration number: Y2021980013807

PC01 Cancellation of the registration of the contract for pledge of patent right