CN109776395A - A kind of cavitation material and the preparation method and application thereof that fluorine-containing spiral shell two is fluorene structured - Google Patents
A kind of cavitation material and the preparation method and application thereof that fluorine-containing spiral shell two is fluorene structured Download PDFInfo
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Abstract
The present invention relates to a kind of cavitation materials that fluorine-containing spiral shell two is fluorene structured, have the structure as shown in general formula I.The cavitation material fluorene structured with spiral shell two provided by the invention is a kind of novel OLED material, it is based on two fluorenes of spiral shell, so as to improve glass transition temperature, molecule thermal stability is strong, with suitable HOMO and lumo energy and higher Eg, photoelectric properties and OLED device service life can be effectively promoted.Fragrant amine groups are introduced simultaneously, there is better planar structure and conjugated system compared with simple two fluorenes of spiral shell, synthesize, purify it is fairly simple, it is low in cost, contain fluorine atom on phenyl ring simultaneously, so as to increase intermolecular distance, the association between compound is prevented, the probability of molecule piled up is reduced.It is less likely to occur to crystallize when vapor deposition, OLED yield rate can be effectively improved by being applied in OLED device, can effectively improve luminous efficiency, good film-forming property.The material can also be used as luminescent material use, can effectively improve the service life of luminescent material.
Description
Technical field
The present invention relates to ORGANIC ELECTROLUMINESCENCE DISPLAYS technical fields, and in particular to a kind of new organic materials and its organic
Application in electroluminescent device.
Background technique
Application of organic electroluminescent (OLED) material in the fields such as information display material, organic optoelectronic material has
Great researching value and fine application prospect.With the development of multimedia information technology, to flat-panel display device performance
It is required that higher and higher.Current main display technology has plasma display apparatus, field emission display and organic electroluminescent
Display device (OLED).Wherein, OLED has itself luminous, low-voltage direct-current driving, all solidstate, the wide, various colors in visual angle etc.
Series of advantages, compared with liquid crystal display device, OLED does not need backlight, and visual angle is wider, low in energy consumption, and response speed is liquid
1000 times of crystal display device, therefore, OLED have broader practice prospect.
For the organic hole transport material reported at present since molecular weight is generally smaller, the glass transition temperature of material is lower,
During materials'use, charging and discharging, material are easy crystallization repeatedly, and the homogeneity of film is destroyed, to influence materials'use
Service life.Therefore, the organic hole transport material of stability and high efficiency is developed, to reduce driving voltage, device light emitting efficiency is improved, prolongs
Long device lifetime has critically important practical application value.
Summary of the invention
The purpose of the present invention is to provide low voltage drive, long-life and the OLED element of high efficiency can be carried out,
And it can provide the compound of such OLED element.
In order to develop the compound with aforesaid properties and use the OLED element of such compound, as a result, it has been found that, lead to
The compound indicated using general formula I is crossed, can reach above-mentioned purpose.That is, the invention proposes a kind of novel organic material, tool
Just like structure shown in general formula I:
In the general formula I, m represents the substitution number of F atom on phenyl ring, can be selected from 1,2 or 3.Specifically, 1,2 or 3
F atom may replace Formulas I ' shown in structure 1,2,3 and/or No. 4 position on H hydrogen atom.
As m=1, F atom may replace Formulas I ' shown in hydrogen atom on 1,2,3 or No. 4 of structure any one position, i.e.,
Structure shown in optional ' -1 of the Formulas I freely~I ' -4 of the organic material, the structure shown in ' -2 preferably such as Formulas I.
As m=2, F atom may replace Formulas I ' shown in structure 1,2,3 and/or No. 4 any two position on hydrogen it is former
Son, i.e., structure shown in described optional ' -5 of the Formulas I freely~I ' -10 of organic material.
As m=3, F atom may replace Formulas I ' shown in structure 1,2,3 and/or No. 4 any three position on hydrogen it is former
Son, i.e., structure shown in described optional ' -11 of the Formulas I freely~I ' -14 of organic material.
Ar in the general formula I1、Ar2、Ar3、Ar4It is independently represented each other the aromatic radical containing n phenyl ring and/or heteroaromatic
Group.The aromatic group can be substituted or unsubstituted mononuclear aromatics, be also possible to substituted or unsubstituted polycyclic aromatic hydrocarbon；Institute
Stating polycyclic aromatic hydrocarbon can be more benzene for rouge hydrocarbon, biphenyl type polycyclic aromatic hydrocarbon or condensed-nuclei aromatics.The n represents 1,2,3,4 or 5.
The Ar1、Ar2The group respectively represented may be the same or different, Ar3、Ar4The group respectively represented can be with
It is identical, it can also be different.
The present invention is to Ar1、Ar2、Ar3、Ar4The group of representative carries out preferably, to further increase the comprehensive performance of material.
Wherein, Ar1、Ar2It is independently represented each other the aromatic group containing n phenyl ring and/or heteroaromatic, n 2,3 or 4；Ar3、Ar4Respectively
From independently representing the aromatic group containing n phenyl ring and/or heteroaromatic, n 1,2,3 or 4.Specifically:
The preferred Ar of the present invention1、Ar2It is each independently selected from following group:
It is highly preferred that Ar1、Ar2It is each independently selected from following group:
It is further preferred that Ar1、Ar2It is each independently selected from following group:
In above-mentioned each preferred embodiment, Ar1、Ar2The group of representative may be the same or different.The preferred Ar of the present invention3、
Ar4It is each independently selected from following group:
It is highly preferred that Ar3, Ar4 are each independently selected from following group:
It is further preferred that Ar3, Ar4 are each independently selected from following group:
As a preferred solution of the present invention, Ar3 is selected from
In above-mentioned each preferred embodiment, Ar3、Ar4The group of representative may be the same or different.
In above-mentioned each substituent group,It indicates to replace position.
Organic material shown in the further preferred general formula I of the present invention is selected from following general formula I-1~I-114 compound represented:
In the general formula I-1~I-114, m is independently represented each other 1,2 or 3, and the specific substitution mode of F atom is for example above
It is described.
Above-mentioned organic compound is based on two fluorenes of spiral shell, and so as to improve glass transition temperature, molecule thermal stability is strong, tool
There are suitable HOMO and lumo energy and higher Eg, can effectively promote photoelectric properties and OLED device service life.Simultaneously
Fragrant amine groups are introduced, there is better planar structure and conjugated system compared with simple two fluorenes of spiral shell, synthesis, purification are simpler
It is single, it is low in cost, while containing fluorine atom on phenyl ring, so as to increase intermolecular distance, prevent forming between compound
It closes, reduces the probability of molecule piled up.It is less likely to occur to crystallize when vapor deposition, being applied in OLED device can effectively improve
OLED yield rate can effectively improve luminous efficiency, good film-forming property.The material can also be used as luminescent material use, can have
Effect improves the service life of luminescent material.
Invention also provides the preparation methods of organic compound shown in general formula I.
The reaction mechanism mechanism of reaction of the preparation method is as follows:
The preparation method using compound A as starting material, withCoupling reaction occurs, obtains compound B, then withCoupling reaction occurs, obtains final goal compound I.
Known common approach can be used to realize in above-mentioned step those skilled in the art, such as selects suitable catalysis
Agent, solvent determine suitable reaction temperature, and time etc., the present invention is not particularly limited this.
As a preferred method of the present invention, the preparation method includes the following steps:
Using toluene as solvent, using acid chloride and tri-tert-butylphosphine as catalyst, potassium tert-butoxide is alkali, in nitrogen protection, control
Temperature 80~120 DEG C under conditions of, compound A withCoupling reaction occurs, obtains compound B, under the same terms again withCoupling reaction occurs, obtains final goal compound I.
The raw materials such as above-mentioned solvent, catalyst, alkali can be closed by public commercial source or methods known in the art
At obtaining.
Invention further provides application of the organic compound shown in general formula I in organic electroluminescence device.This
Invent the hole mobile material that the preferably organic compound is used as hole transmission layer in organic electroluminescence device.
It include shown in general formula I of the present invention the present invention also provides a kind of organic electroluminescence device, in organic function layer
Organic compound.The preferably described organic compound of the present invention is used as the hole transport material of organic function layer hole-transporting layer
Material.The thickness of the hole transmission layer can be 10~50nm, preferably 27~33nm.
As a preferred solution of the present invention, above-mentioned organic electroluminescence device successively includes transparent base from the bottom to top
Hole transmission layer that piece, anode layer, organic compound shown in general formula I are constituted, electroluminescence layer, electron transfer layer, electronics note
Enter layer and cathode layer.
Wherein, glass substrate or flexible substrate can be selected in the material for constituting the transparent substrate, and tradition specifically can be used
Substrate in organic luminescent device, such as glass substrate or plastic base, preferably use glass substrate.
Inorganic material can be selected in the material for constituting the anode layer, and tin indium oxide (ITO), zinc oxide, oxygen specifically can be selected
Change at least one of tin zinc, gold, silver or copper, preferably tin indium oxide (ITO).
The material of main part for constituting the electroluminescence layer can be selected from any one in following compound, preferably CBP
(bis- carbazoles of 4,4'-N, N'--biphenyl):
Dopant can also be added by constituting in the material of the electroluminescence layer, such as (piq) 2Ir (acac) [two-(1- benzene
Base isoquinolyl) acetylacetone,2,4-pentanedione iridium (III)].
The material for constituting the electron transfer layer can be selected from any one in following compound:
The material for constituting the electron injecting layer can be selected from LiF, Li2O、MgO、Al2O3One of, preferably LiF.
The material choosing for constituting the cathode can be from one of lithium, magnesium, silver, calcium, strontium, aluminium, indium, copper, Jin Heyin, preferably
Aluminium.
In order to ensure playing synergistic effect in the luminescent device between the material of each layer, the present invention is also to the photophore
The thickness of each layer carries out preferably in part, so that the luminescent device plays optimal resultant effect.
Specifically, the thickness of the hole transmission layer can be 10~50nm, preferably 27~33nm；The electroluminescent hair
The thickness of photosphere can be 10~100nm, preferably 27~33nm；The thickness of the electron transfer layer can be 10~30nm,
Preferably 18~22nm；The thickness of the electron injecting layer can be 5-~30nm, preferably 9~11nm；The cathode layer
Thickness can be 50~200nm, preferably 100~200nm.
Novel OLED material provided by the invention is based on 9,9 ' spiral shell, two fluorenes, using aminated compounds as end group, by
The active position of polycyclc aromatic compound introduces the arylamine class substituent group with hole transport performance, obtains a kind of tool
There is the novel OLED material of hole transmission performance.Such material has a high hole mobility, preferable thin film stability and suitable
The molecular entergy level of conjunction, high luminous efficiency can be used in field of organic electroluminescence, use as hole mobile material.
Specific embodiment
The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention..
The synthetic method of part main compound in the present invention is described below.
Embodiment 1
Synthetic route is as follows:
It comprises the following specific steps that:
The synthesis of compound B-23-2
500 milliliters of there-necked flasks match magnetic agitation, sequentially add potassium tert-butoxide 18.1g (0.188mol), N- after argon gas displacement
([1,1 '-biphenyl] -4- base) the fluoro- 2- amine 33.34g of -9H- (purity 99%, 0.1mol) and toluene 100ml.Nitrogen is replaced again
After sequentially add 1.6ml tri-tert-butylphosphine and 0.23g acid chloride.After adding, it is heated to 85 DEG C.Start be added dropwise by
Fluorine-containing two fluorenes of spiral shell, the two bromine substituent class compound (1-1) (purity 99%, 0.1mol) of 49.22g and 100ml toluene form molten
Liquid, 80-120 DEG C of temperature control.Be cooled to 50 DEG C, the hydrolysis of 100m deionized water be added, stirs 10 minutes, filtering, filter cake with DMF repeatedly
It boils several times, revolving obtains 64.67g white solid, purity 99%, yield 89%.
The synthesis of compound I-23-2
500 milliliters of there-necked flasks match magnetic agitation, sequentially add potassium tert-butoxide 18.1g (0.188mol), N- after argon gas displacement
(4- fluorophenyl) -4 ' methyl-[1,1 '-biphenyl] -4- amine 27.73g (purity 99%, 0.1mol).Again after nitrogen displacement successively
1.6ml tri-tert-butylphosphine and 0.23g acid chloride is added.After adding, it is heated to 85 DEG C.Start to be added dropwise by compound B-
The solution of 23-2 and 100ml toluene composition, 80-120 DEG C of temperature control.50 DEG C are cooled to, the hydrolysis of 100m deionized water, stirring 10 is added
Minute, filtering, filter cake is boiled several times repeatedly with DMF, and revolving obtains 85.64g product, purity 99%, yield 91%.
Product MS (m/e): 941.11；Elemental analysis (C69H46F2N2): theoretical value C:88.06%, H:4.93%, F:
4.04%, N:2.98%；Measured value C:88%, H:4.99%, F:4.04%, N:2.98%.
Embodiment 2
Synthetic route is as follows:
It comprises the following specific steps that:
The synthesis of compound B-24-2
500 milliliters of there-necked flasks match magnetic agitation, sequentially add potassium tert-butoxide 18.1g (0.188mol), N- after argon gas displacement
(1,1 '-xenyl) -9H- fluorenes -2- amine 33.34g (purity 99%, 0.1mol) and toluene 100ml.Again after nitrogen displacement successively
1.6ml tri-tert-butylphosphine and 0.23g acid chloride is added.After adding, it is heated to 85 DEG C.Start to be added dropwise fluorine-containing by 49.22g
The solution of two fluorenes of spiral shell, two bromine substituent class compound (purity 99%, 0.1mol) and 100ml toluene composition, 80-120 DEG C of temperature control.
50 DEG C are cooled to, the hydrolysis of 100m deionized water is added, stirs 10 minutes, filtering, filter cake is boiled several times repeatedly with DMF, obtained
65.52g white solid, purity 99%, yield 88%.
The synthesis of compound I-24-2
500 milliliters of there-necked flasks match magnetic agitation, sequentially add potassium tert-butoxide 18.1g (0.188mol), N- after argon gas displacement
(4- fluorophenyl) -5- (p-methylphenyl) pyridine -2- amine 27.3g (purity 99%, 0.1mol) and toluene 100ml.Nitrogen is set again
1.6ml tri-tert-butylphosphine and 0.23g acid chloride are sequentially added after changing.After adding, it is heated to 85 DEG C.Start to be added dropwise by chemical combination
The solution of object B-24-2 and 100ml toluene composition, 80-120 DEG C of temperature control.50 DEG C are cooled to, the hydrolysis of 100m deionized water is added, stirs
It mixes 10 minutes, filters, filter cake is boiled several times repeatedly with DMF, obtains 83.85g product, purity 99%, yield 89%.
Product MS (m/e): 942.10；Elemental analysis (C66H43F2N3): theoretical value C:86.69%, H:4.81%, F:
4.03%, N:4.46%；Measured value C:86.68%, H:4.82%, F:4.03%, N:4.46%.
Embodiment 3
Synthetic route is as follows:
It comprises the following specific steps that:
The synthesis of compound B-114-2
500 milliliters of there-necked flasks match magnetic agitation, sequentially add potassium tert-butoxide 18.1g (0.188mol), N- after argon gas displacement
(1,1 '-xenyl) dibenzothiophenes -3- amine 35.14g (purity 99%, 0.1mol) and toluene 100ml.Again after nitrogen displacement
Sequentially add 1.6ml tri-tert-butylphosphine and 0.23g acid chloride.After adding, it is heated to 85 DEG C.Start to be added dropwise and be contained by 49.22g
The solution of two fluorenes of fluorine spiral shell, two bromine substituent class compound (purity 99%, 0.1mol) and 100ml toluene composition, temperature control 80-120
℃.50 DEG C are cooled to, the hydrolysis of 100m deionized water is added, stirs 10 minutes, filtering, filter cake is boiled several times repeatedly with DMF, obtained
69.02g white solid, purity 99%, yield 90.5%.
The synthesis of compound I-114-2
500 milliliters of there-necked flasks match magnetic agitation, sequentially add potassium tert-butoxide 18.1g (0.188mol), N- after argon gas displacement
(4- fluorophenyl) -3- (pyridin-4-yl) aniline 26.43g (purity 99%, 0.1mol).It is sequentially added after nitrogen displacement again
1.6ml tri-tert-butylphosphine and 0.23g acid chloride.After adding, it is heated to 85 DEG C.Start to be added dropwise by compound B-114-2 and
The solution of 100ml toluene composition, 80-120 DEG C of temperature control.50 DEG C are cooled to, the hydrolysis of 100m deionized water is added, stirs 10 minutes,
Filtering, filter cake are boiled several times repeatedly with DMF, obtain 82.31g product, yield 87%.
Product MS (m/e): 946.11；Elemental analysis (C66H41F2N3S): theoretical value C:83.79%, H:4.37%, F:
4.02%, N:4.44%, S:3.39%；Measured value C:83.78%, H:4.38%, F:4.02%, N:4.44%, S:3.39%.
Intermediate N ([1,1 '-biphenyl] -4- base) fluoro- 2- amine of -9H- etc. can be from Beijing Yan Huaji used in the process of test
Join photoelectricity technology corporation, Ltd.'s purchase gained.
According to embodiment 1, the technical solution of embodiment 2 and embodiment 3, it is only necessary to which the corresponding raw material of simple replacement does not change
Become any substantive operations, following compound can be synthesized:
Embodiment 4:OLED device
Present embodiments provide one group of OLED device, preparation method specifically:
(1) glass substrate for being coated with ITO conductive layer is ultrasonically treated 30 minutes in cleaning agent, is rushed in deionized water
It washes, at acetone/ethanol in the mixed solvent ultrasound 30 minutes, is baked to is completely dried under a clean environment, use ultraviolet rays cleaning
Machine irradiates 10 minutes, and with low energy cation beam bombarded surface；
(2) the above-mentioned ito glass substrate handled well is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-4Pa exists
Vacuum evaporation compound 2-TNATA on above-mentioned anode tunic forms the hole injection layer with a thickness of 60nm；Hole injection layer it
Film thickness is deposited as hole transmission layer, evaporation rate 0.2nm/s in the compound I-23-2 that upper vacuum evaporation embodiment 1 provides
For 30nm；
(3) electroluminescence layer, concrete operations are formed on above-mentioned hole transmission layer are as follows: luminescent layer material of main part will be used as
CBP [bis- carbazoles of 4,4'-N, N'--biphenyl] is placed in the cell of vacuum phase deposition equipment, by (piq) as dopant
2Ir (acac) [two-(1- phenyl isoquinolin quinoline base) acetylacetone,2,4-pentanedione iridium (III)] is placed on another room of vacuum phase deposition equipment
In, two kinds of materials are evaporated simultaneously with different rates, the concentration of (piq) 2Ir (acac) is 5%, and vapor deposition total film thickness is 30nm；
(4) continue that electron transfer layer of the one layer of compound BCP as device, vapor deposition speed is deposited on the electroluminescence layer
Rate is 0.2nm/s, and vapor deposition film thickness is 20nm；The structure of the BCP are as follows:
(5) continue that electron injecting layer of the one layer of LiF as device is deposited on the electron transfer layer, evaporation rate is
0.2nm/s, vapor deposition film thickness are 10nm；
(6) continue that cathode of the one layer of Al as device, evaporation rate 0.2nm/ is deposited on the electron injecting layer
S, vapor deposition film thickness are 150nm；OLED device provided by the invention is obtained, OLED-1 is denoted as.
According to upper identical step, only by the compound I-23-2 in step (2) replace with embodiment 2 offer chemical combination
Object I-24-2 obtains OLED-2 provided by the invention.
According to upper identical step, only by the compound I-23-2 in step (2) replace with embodiment 3 offer chemical combination
Object I-114-2 obtains OLED-3 provided by the invention.
According to upper identical step, the compound I-23-2 in step (2) is only replaced with into NPB (control compounds 1),
Obtain OLED-4 provided by the invention.The structure of the NPB specifically:
The present invention detects the performance of above-mentioned obtained device OLED-1~OLED-4, and testing result is as shown in table 1.
Table 1:OLED device performance testing result
From the foregoing, it will be observed that device OLED-1, OLED-2 for being prepared into using organic material shown in Formulas I provided by the invention and
The operating voltage of OLED-3 is lower, and brightness under the same conditions, current efficiency is obviously than NPB as hole mobile material
Device OLED-4 is much higher, and the service life of device is obviously prolonged very much.
Although above having used general explanation, specific embodiment and test, the present invention is made to retouch in detail
It states, but on the basis of the present invention, it can be made some modifications or improvements, this is apparent to those skilled in the art
's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to claimed
Range.
Claims (10)
1. a kind of cavitation material that fluorine-containing spiral shell two is fluorene structured, which is characterized in that have the structure as shown in general formula I:
In the general formula I, m be 1~3 integer；
Ar1、Ar2、Ar3、Ar4Be independently represented each other the aromatic group containing n phenyl ring and/or heteroaromatic, n be 1~5 it is whole
Number.
2. cavitation material according to claim 1, which is characterized in that Ar1、Ar2It is independently represented each other containing n phenyl ring
And/or the aromatic group of heteroaromatic, n 2,3 or 4；
Ar3、Ar4It is independently represented each other the aromatic group containing n phenyl ring and/or heteroaromatic, n 1,2,3 or 4.
3. cavitation material described in any one according to claim 1~2, which is characterized in that Ar1、Ar2It is each independently selected from
Following group:
Ar3、Ar4It is each independently selected from following group:
4. cavitation material according to any one of claims 1 to 3, which is characterized in that Ar1、Ar2It is each independently selected from
Following group:
Ar3、Ar4It is each independently selected from following group:
5. cavitation material described in any one according to claim 1~4, which is characterized in that Ar1、Ar2It is each independently selected from
Following group:
Ar3、Ar4It is each independently selected from following group:
6. cavitation material described in any one according to claim 1~5, which is characterized in that Ar3It is selected from
7. cavitation material according to claim 1, which is characterized in that the organic compound be selected from following general formula I-1~
I-114 compound represented:
8. the preparation method of cavitation material described in claim 1~7 any one, which is characterized in that the reaction mechanism mechanism of reaction is as follows:
The preparation method using compound A as starting material, withCoupling reaction occurs, obtains compound B, then withCoupling reaction occurs, obtains final goal cavitation material I；
Preferably, the preparation method includes the following steps:
Using toluene as solvent, using acid chloride and tri-tert-butylphosphine as catalyst, potassium tert-butoxide is alkali, in nitrogen protection, temperature control 80
Under conditions of~120 DEG C, compound A withCoupling reaction occurs, obtains compound B, under the same terms again with
Coupling reaction occurs, obtains final goal cavitation material I.
9. application of the cavitation material described in claim 1~7 any one in organic electroluminescence device；
Preferably, the cavitation material is used as the hole mobile material of hole transmission layer in organic electroluminescence device.
It include hole described in claim 1~7 any one in organic function layer 10. a kind of organic electroluminescence device
Material；
Preferably, the cavitation material is used as the hole mobile material of organic function layer hole-transporting layer；
It is highly preferred that the hole transmission layer with a thickness of 10~50nm.
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| CN112538046A (en) * | 2019-09-20 | 2021-03-23 | 常州强力昱镭光电材料有限公司 | Organic compound with azaspirobifluorene structure and application thereof |
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Application publication date: 20190521 |