CN106220652B - Electroluminescent organic material and the organic light emitting diode device for using the luminescent material - Google Patents

Electroluminescent organic material and the organic light emitting diode device for using the luminescent material Download PDF

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CN106220652B
CN106220652B CN201610589216.5A CN201610589216A CN106220652B CN 106220652 B CN106220652 B CN 106220652B CN 201610589216 A CN201610589216 A CN 201610589216A CN 106220652 B CN106220652 B CN 106220652B
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light emitting
emitting diode
organic material
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bonded
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CN106220652A (en
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赵洪玉
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北京拓彩光电科技有限公司
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D519/00Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/005Macromolecular systems with low molecular weight, e.g. cyanine dyes, coumarine dyes, tetrathiafulvalene
    • H01L51/0062Macromolecular systems with low molecular weight, e.g. cyanine dyes, coumarine dyes, tetrathiafulvalene aromatic compounds comprising a hetero atom, e.g.: N,P,S
    • H01L51/0071Polycyclic condensed heteroaromatic hydrocarbons
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/005Macromolecular systems with low molecular weight, e.g. cyanine dyes, coumarine dyes, tetrathiafulvalene
    • H01L51/0062Macromolecular systems with low molecular weight, e.g. cyanine dyes, coumarine dyes, tetrathiafulvalene aromatic compounds comprising a hetero atom, e.g.: N,P,S
    • H01L51/0071Polycyclic condensed heteroaromatic hydrocarbons
    • H01L51/0072Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ringsystem, e.g. phenanthroline, carbazole
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/50Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof specially adapted for light emission, e.g. organic light emitting diodes [OLED] or polymer light emitting devices [PLED]
    • H01L51/5012Electroluminescent [EL] layer
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    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1029Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1092Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom

Abstract

The present invention relates to the organic light emitting diode devices of new Organic Electro Luminescent Materials and the use luminescent material, belong to organic electronic field of luminescent technology.The new Organic Electro Luminescent Materials of the present invention, its structural formula is one of Formulas I, II, III, wherein Y is expressed as one in following carbazole quinoline group, X be expressed as hydrogen, the aromatic group of substituted or unsubstituted carbon atom number 6 30, substituted or unsubstituted carbon atom number 5 30 heteroaromatic group, Y and X be bonded to five yuan or hexatomic ring, hetero atom is N, S, O in the heterocycle.Experiment shows, the new Organic Electro Luminescent Materials of the present invention are the phosphorescent compound with high triplet energy, using the phosphorescent compound as the main body of the luminescent layer of Organic Light Emitting Diode, the energy transfer in luminescent layer is thereby promoted, and improves the green emission efficiency and service life of organic luminous layer.

Description

Electroluminescent organic material and the organic light emitting diode device for using the luminescent material

Technical field

The present invention relates to a kind of new Organic Electro Luminescent Materials and a kind of Organic Light Emitting Diode (OLED) device, more For body, it is related to a kind of novel electroluminescent for the luminous efficiency for having because of high triplet energy and wide bandgap and improving Material and a kind of OLED device using the new Organic Electro Luminescent Materials.

Background technology

In recent years, extensive research and development had been carried out to organic electroluminescence device.In the basic of this light-emitting component In structure, between the layer containing luminescent substance is inserted in a pair of electrodes, by applying on voltage to the element, it can get and come from shiner The light emitting of matter.

Since this light-emitting component is self-emission device, they relative to liquid crystal display in high pixel visibility and Save has advantage to the aspect of backlight demand, is thus for example deemed suitable for flat panel displaying element.Light-emitting component is equally Ceiling advantage, because they are thin and light-weight.The response of very high speed is one of the feature of this element.

Further, since this light-emitting component can be formed in the form of a film, therefore planar light emission can be provided.Therefore, It can easily form the element with large area.This is to be difficult to use using incandescent lamp and LED as the point light source of representative or with fluorescence Lamp is the feature that the linear light sorurce of representative obtains.Therefore, light-emitting component is also flat as can be applied to illuminate with big potentiality Area source etc..

The excitation state formed by organic compound can be singlet or triplet state.From singlet excited state (S*) Transmitting is fluorescence, and comes from triplet excited states (T*) transmitting be referred to as phosphorescence.Additionally, it is believed that its statistics life in light-emitting component At than for S*:T*=1:3.In by the energy conversion of singlet excited state for photoemissive compound, do not see at room temperature The transmitting from triplet excited states is observed, and only observes the transmitting from singlet excited state.It is therefore contemplated that using glimmering The interior two words efficiency of the light-emitting component of optical compounds has 25% theoretical limit, is based upon 1:3 S*With T*The ratio between.Therefore have Machine electromechanical phosphorescent material is a kind of material for being attracted attention recently, and the organic electroluminescence with high luminous efficiency and luminous brightness is sent out Luminescent material, by the method for introducing heavy metal atom the triplet transition prohibited originally at room temperature is utilized, to make inside in it Quantum efficiency theory can reach 100%, be single fluorescent material 4 times (1, Cao Y., Parker I.D., Heeger J., Nature,1999,397:414-417.2、Wohlgenann M.,et al.Nature,2001,409:494-497.).It is organic The common heavy metal atom of electromechanical phosphorescent material is mostly transition metal, wherein the most detailed with the most widely used of iridium, research, this is Because metal iridium complex has high efficiency, at room temperature stronger phosphorescent emissions and can be by the adjustment of ligand structure Adjusting emission wavelength makes the color of electroluminescent device cover entire visible region.Therefore design studies synthesizing new is efficiently golden Belong to complex of iridium, split phosphorescing materia is of great significance.

But the efficiency of dopant is because Quenching acutely reduces, thus shining for the dopant without main body There is limitation in layer.Accordingly, it is desirable to be formed with main body with more high thermal stability and triplet energy state by dopant Luminous material layer.

In the OLED device comprising phosphorescent compound, the hole from anode and the electronics from cathode are in luminescent material It is combined at the main body of layer.The singlet exciton of main body occurs to the singlet of dopant or the energy level transition of triplet, and Carry out the energy level transition of the triplet excitons of autonomous agent to the triplet of dopant.Transit to the singlet energy of dopant The exciton of grade transits to the triplet of dopant again.The exciton transition of the triplet of dopant makes hair to ground state Photosphere shines.

To realize that the efficient energy level transition for transitting to dopant, the triplet energy state of main body should be more than three lines of dopant State energy.When the triplet of main body is less than the triplet energy state of dopant, occur by the anti-of dopant to main body energy Transition makes luminous efficiency reduce.

The CBP for being widely used in main body has the triplet of 2.6eV, and there are about the highest energy level of -6.3eV, peace treaties - The lowest energy level of 2.8eV.Therefore triplet 2.8eV, the blue light of highest energy level -5.8eV and lowest energy level -3.0eV are utilized Dopant FCNIr, it may occur that the anti-transition of energy level of dopant to main body makes luminous efficiency reduce.In particular, luminous efficiency drops Low generation is more notable under cryogenic.

Invention content

The present invention relates to a kind of new Organic Electro Luminescent Materials and a kind of using the new Organic Electro Luminescent Materials OLED device, the two solve the problems, such as one or more caused by the limitation and defect of the prior art substantially.

It is an object of the present invention to provide a kind of new Organic Electro Luminescent Materials, the novel electroluminescent Material has high triplet energy state and wide band gap, and strong electron transport ability.

It is a further object to provide a kind of OLED with higher photoluminescence efficiency.

The new Organic Electro Luminescent Materials of the present invention, structural formula are one of Formulas I, II, III:

Wherein X is expressed as one in following carbazole quinoline isomers, and 9 N atoms and Y are bonded in carbazole quinoline group,

Y is expressed as the aromatic group of substituted or unsubstituted carbon atom number 6-30, substituted or unsubstituted carbon atom number 5- Phenyl ring on 30 heteroaromatic group, Y and X is bonded to five yuan or hexatomic ring, and hetero atom is N, S, O in the heterocycle.

The Y is one of following groups:

The substituted group is the alkyl of C1-C4.

The Y is substituted or unsubstituted hexatomic ring or five-membered ring, and the Y and X is bonded to five yuan or hexatomic ring.

The Y and X is bonded to five yuan or the structure of hexatomic ring is as follows:

Preferentially:N atoms in structural formula I, II, III and the C atoms in carbazole quinoline on phenyl are bonded.

It is preferred that:Structural formula I, II, the C atoms on N atoms and phenyl in carbazole quinoline 6 are bonded.

Preferred compound is:

Organic light emitting diode device prepared by above-mentioned material.

Experiment shows that new Organic Electro Luminescent Materials of the invention are the phosphorescent compound with high triplet energy, Using the phosphorescent compound as the main body of the luminescent layer of Organic Light Emitting Diode, the energy in luminescent layer is thereby promoted Transfer, and improve the green emission efficiency and service life of organic luminous layer.

Description of the drawings

D intermediate nuclear-magnetisms in Fig. 1, main body one.

The nuclear-magnetism of Fig. 2, one intermediate E of main body.

Fig. 3, one DSC of main body.

Fig. 4, Comparative Example D SC.

Specific implementation mode

The present invention provides novel phosphorescent compound preparation method, to keep the purpose of the present invention, technical solution, effect more clear It is clear, complete, it is the further description to the present invention below.It should be appreciated that embodiment herein is only used for explaining the present invention, Be not intended to limit the present invention, it is all meet the scope of the invention all within protection.

The preparation of embodiment 1, the first main body

The synthesis of intermediate C:

0.1mol A, 0.2mol B, sodium tert-butoxide 0.2mol, 0.002mol palladium are separately added into 2L four-hole bottles, 1L first 2L four-hole bottles, stirring is added in benzene, and inflated with nitrogen 30 minutes is added 1ML tri-tert-butylphosphines, is heated to reflux 4 hours, and cooling is filtered To mother liquor.Concentrated mother liquor obtains light yellow solid.Mass spectrum (ESI, 245.3)

Intermediate D (CAS:1800071-10-6, CN104725373Phosphorescent compound, Preparation method and organic light emitting diode device) synthesis:

0.1molC is dissolved in 300ML DMF, and 50 degree of fully dissolveds are added dropwise 0.1mol NBS and are gradually precipitated greyish white with dropwise addition Color solid.NBS is dripped off, and is stirred overnight, cold filtration, obtains pale solid D.Attached drawing 1 is shown in detection.

The synthesis of compound 1:

0.1mol D、0.1molE(14H-Benzo[c][1]benzothieno[2,3-a]carbazole,CAS: 1313395-18-4 is prepared according to 20140332793 synthetic methods of patent US) 1L four-hole bottles were added, toluene is added Acid chloride 0.02mol, tri-tert-butylphosphine 0.04mol, nitrogen charging is added portionwise in 400ML, sodium tert-butoxide 0.2mol, stirring, inflated with nitrogen Gas 30 minutes, is refluxed overnight.Cooling, filtering obtains light yellow solid, 565.69 (MODI-TOF) of simpleness detection

Embodiment 2:The preparation of second main body

The synthesis of intermediate C:

0.1mol A, 0.2mol B, sodium tert-butoxide 0.2mol, 0.002mol palladium are separately added into 2L four-hole bottles, 1L first 2L four-hole bottles, stirring is added in benzene, and inflated with nitrogen 30 minutes is added 1ML tri-tert-butylphosphines, is heated to reflux 4 hours, and cooling is filtered To mother liquor.Concentrated mother liquor obtains light yellow solid C.Mass spectrum (ESI, 245.3)

The synthesis of intermediate D:

The synthesis of D can be with bibliography Journal of Organic Chemistry, 76 (9), 2976-2993;2011, The synthetic methods of 9,9- diphenylacridines synthesizes.

The synthesis of intermediate F:

0.1molC is dissolved in 300ML DMF, and 50 degree of fully dissolveds are added dropwise 0.1mol NBS and are gradually precipitated greyish white with dropwise addition Color solid.NBS is dripped off, and is stirred overnight, and cold filtration obtains pale solid.

The synthesis of compound 2:

0.1mol F、0.1mol(14H-Benzo[c][1]benzothieno[2,3-a]carbazole,CAS 1313395-18-4 is prepared according to 20140332793 synthetic methods of patent US) 1L four-hole bottles were added, toluene is added Potassium carbonate 0.2mol is added portionwise in 400ML, ethyl alcohol 200ML, water 200ML, stirring, and acid chloride is added in inflated with nitrogen 30 minutes 0.5G, tri-tert-butylphosphine 1ML, is refluxed overnight.Cooling, filtering obtains light yellow solid, 486.5 (MODI-TOF) of simpleness detection

Embodiment 3, the synthesis of third main body

2,3- dibromo pyridines are obtained into chemical combination as raw material according to the patent CN102612518 synthetic routes having disclosed Object G.With reference to main body one, two synthetic methods, main body three is obtained.

Embodiment 4, the synthesis of the 4th main body

According to the synthetic route of main body two, methyl-magnesium-bromide replaces phenyl-magnesium-bromide, obtains material of main part four.

Embodiment 5, the 5th main body

It is easy to prepare intermediate F according to patent US 20140332793, according to the synthetic method of embodiment 4, be led Body five.

Comparative example:

2- (4- bromobenzenes) -4,6- diphenyl-central Shanxi plain is as raw material, according to synthetic method above, it is easy to be compared Example compound.

Measure according to the first to the 5th material of main part prepared by above-mentioned synthesis example of implementation of the present invention and by with Ultra-violet absorption spectrum and photoluminescence spectra of the material for the comparative example that lower chemical formula indicates under low temperature (for example, 77K), show Show in result table below.

Comparative example

Table 1:

Energy level LUMO(Ev) HOMO(Ev) Triplet (Ev) Comparative example 2.65 -3.20 -5.85 2.50 First main body 2.75 -3.35 -6.10 2.65 Second main body 2.78 -3.31 -6.09 2.67 Third main body 2.82 -3.30 -6.12 2.71 4th main body 2.90 -3.33 -6.23 2.73 5th main body 2.87 -3.35 -6.17 2.77

As it can be seen from table 1 main body two is all higher than 2.65ev to five triplet state of main body, red, green phosphorescent material can be met Expect the requirement of main body.

It is described below to use and be formed by by above-mentioned second and third material of main part;Green light phosphorescent compound and compare Production Example of the material of example as the Organic Light Emitting Diode of green body.

Ito substrate is patterned, makes its light-emitting area 3mmX3mm, is then cleaned.Ito substrate is put into very After in empty room, it is 1X10 to make base pressure-6Support.Then, it on being used to form the ITO of anode, forms the HATCN that thickness is about 50 angstroms and uses In hole injection layer, forms the NPD that thickness is about 550 angstroms and be used for hole transmission layer, form the TAPC that thickness is about 100 angstroms and be used for Hole injection layer, forms the second material of main part that thickness is about 300 angstroms and the GD that doping concentration is about 15% is used for luminescent layer.So Afterwards, it forms the TmPyPb that thickness is 400 angstroms and is used for electron supplying layer, form the LiF that thickness is about 5 angstroms and be used for electron injecting layer, And the Al layer cathodes of 1100 angstroms of formation.Then, it is packaged process using UV curability encapsulant and hygroscopic agent, is formed and is shone Diode.

Production Example 2

Using manufacturing process same as described above, Organic Light Emitting Diode is manufactured, it is unique the difference is that using third main body As light emitting host.

Comparative example

Using technique identical with Production Example 1, Organic Light Emitting Diode is manufactured, it is unique the difference is that using comparative example main body As light emitting host.

Starting voltage (volt) Luminous efficiency (Cd/A) Launch wavelength (nm) Service life (95%) Embodiment 1 3.2 18.2 530 40000 hours Embodiment 2 3.1 20.1 530 38000 hours Comparative example 4.5 15.3 531 28000 hours

As shown in table 2, it has been confirmed that compared with comparative example, the Organic Light Emitting Diode manufactured according to Production Example 1 is being shown When the chromaticity coordinates of phase same level, the improvement of luminous efficiency, quantum efficiency and service life is shown.In particular, greatly improving The service life of Organic Light Emitting Diode.

As described above, the implementation of the present invention has manufactured the phosphorescent compound with high triplet energy, and use institute Main body of the phosphorescent compound stated as the luminescent layer of Organic Light Emitting Diode, thereby promotes the energy transfer in luminescent layer, And improve the green emission efficiency and service life of organic luminous layer.

Although embodiments of the present invention are illustrated by reference to its numerous description embodiment, but should Understand, those skilled in the art, which can design, will fall into many other improvement and implementation within the scope of disclosure principle Mode.More specifically, theme combination of the various changes and modifications within the disclosure, attached drawing and scope of the appended claims It is possible in terms of the composition part of arrangement and/or arrangement.In addition to the changes and improvements in terms of composition part and/or arrangement, replace Transsexual application also will be apparent for those skilled in the art.

Claims (10)

1. a kind of electroluminescent organic material, structural formula is one of Formulas I, II:
Wherein X is expressed as one in following carbazole quinoline isomers, and 9 N atoms and Y are bonded in carbazole quinoline group,
Y is expressed as the heteroaromatic group of substituted or unsubstituted carbon atom number 5-30,
Or Y is expressed as the aromatic group of substituted or unsubstituted carbon atom number 6-30, substituted or unsubstituted carbon atom number 5- 30 heteroaromatic group and Y is bonded to five yuan or hexatomic ring with the phenyl ring on X,
Hetero atom is N, S, O in the heterocycle.
2. electroluminescent organic material according to claim 1, the Y is one of following groups:
3. electroluminescent organic material according to claim 1, the Y is substituted or unsubstituted hexatomic ring or five yuan Ring, substituted group are the alkyl of C1-C4.
4. electroluminescent organic material according to claim 1, the Y and X is bonded to five yuan or hexatomic ring.
5. electroluminescent organic material according to claim 4, the Y and X is bonded to the structure of five yuan or hexatomic ring such as Under:
6. electroluminescent organic material according to claim 1, in the N atoms and carbazole quinoline in structural formula I, II on phenyl C atoms it is bonded.
7. electroluminescent organic material according to claim 6, phenyl 6 in the N atoms and carbazole quinoline in structural formula I, II C atoms on position are bonded.
8. electroluminescent organic material according to claim 7, structural formula are:
9. a kind of organic light emitting diode device, including any luminescent materials of claim 1-8.
10. organic light emitting diode device according to claim 9, any luminous materials of the claim 1-8 Expect the material of main part as luminescent layer.
CN201610589216.5A 2016-07-22 2016-07-22 Electroluminescent organic material and the organic light emitting diode device for using the luminescent material CN106220652B (en)

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US20160013430A1 (en) * 2014-07-10 2016-01-14 Samsung Display Co., Ltd. Organic light-emitting device
US20160020412A1 (en) * 2014-07-10 2016-01-21 Samsung Display Co., Ltd. Organic light-emitting device
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US20150380662A1 (en) * 2014-06-30 2015-12-31 Samsung Display Co., Ltd. Organic light-emitting device
US20160013430A1 (en) * 2014-07-10 2016-01-14 Samsung Display Co., Ltd. Organic light-emitting device
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CN105586030A (en) * 2014-11-10 2016-05-18 三星显示有限公司 Organic Light-Emitting Device

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