CN106279103A - A kind of pyrimidines and application thereof and organic luminescent device - Google Patents
A kind of pyrimidines and application thereof and organic luminescent device Download PDFInfo
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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Abstract
The present invention provides a kind of pyrimidines and application thereof and organic luminescent device, belongs to organic photoelectrical material technical field.This pyrimidines has structure shown in formula I, can serve as the electron transport material in organic electroluminescence device, hole mobile material or luminescent material, has lower driving voltage, higher luminous efficiency.Using the organic electroluminescence device prepared of pyrimidines that the present invention provides, luminous efficiency is up to 13～15cd/A, and driving voltage, up to 3.9V, is the luminous organic material of function admirable.
Description
Technical field
The present invention relates to organic photoelectrical material technical field, be specifically related to a kind of pyrimidines and application thereof with organic
Luminescent device.
Background technology
At present, display screen is main with TFT (Thin Film Transistor, TFT)-LCD, due to
It is the display of non-self luminescence, it is therefore necessary to through backlight throw light, and sequentially penetrate the polarisation in TFT-LCD panel
The relevant spare parts such as plate, glass substrate, liquid crystal layer, colored filter, glass substrate, Polarizer, the eyes finally entering people become
Picture, can be only achieved the function of display.Just because of the display process of above-mentioned complexity, its display screen occurs in actual application
The shortcomings such as reaction rate is slow, power consumption, narrow viewing angle, are not enough to become perfect display screen.
Organic electroluminescent LED (OLEDs) has existing aobvious in each performance as a kind of brand-new Display Technique
The advantage that technology of showing is unmatched, as have all solid state, from main light emission, brightness height, high-resolution, visual angle width (more than 170 degree),
Fast response time, thickness are thin, volume is little, lightweight, can use flexible base board, low-voltage direct-current drive (3-10V), low in energy consumption,
Operating temperature range width etc. so that its application market is quite varied, such as illuminator, communication system, car-mounted display, portable
Electronic equipment, fine definition show even military field.
Among organic electroluminescent LED, when electronics and hole in organic molecule in conjunction with after, can because electronics from
The difference of rotation symmetric mode, produces the form of two kinds of excited state, and one accounts for 25% for singlet state, and one is triplet 75%.
It is generally believed that the limit of the internal quantum of fluorescent material usually organic small molecule material is 25%.And phosphor material by
In the Effect of Spin-orbit Coupling that heavy atoms effect causes, it is possible to use the energy of the triplet exciton of 75%, so having no to doubt
That asks improves luminous efficiency.
But, the use that presently disclosed luminescent material still can not meet OLED at aspect of performances such as luminous efficiencies is wanted
Ask, therefore, design and find a kind of compound, as OLED new material to overcome it to occur not in actual application
Foot, is the emphasis in OLED material research work and Development Trend from now on.
Summary of the invention
It is an object of the invention to provide a kind of pyrimidines and application thereof and organic luminescent device, use this chemical combination
The organic luminescent device of thing has lower driving voltage, higher luminous efficiency.
The invention provides a kind of pyrimidines, its general structure is as shown in formula I:
Wherein, X1、X2Independently selected from C or N；
R1、R2、R3Independently selected from the aryl of substituted or unsubstituted C6～C60, substituted or unsubstituted C10～C60
Thick aryl, the heteroaryl of substituted or unsubstituted C5～C60.
Preferably, described pyrimidines such as formula (I-1) or formula (I-2) are shown:
Wherein, R1、R2、R3Independently selected from the aryl of substituted or unsubstituted C6～C60, substituted or unsubstituted C10～
The thick aryl of C60, the heteroaryl of substituted or unsubstituted C5～C60.
Preferably, described R1、R2、R3Aryl, replacement or unsubstituted independently selected from substituted or unsubstituted C6～C20
The thick aryl of C10～C20, the heteroaryl of substituted or unsubstituted C5～C20.
Preferably, the hetero atom in described heteroaryl is N.
Preferably, described R1、R2、R3Independently selected from phenyl, xenyl, terphenyl, naphthyl, anthryl, phenanthryl, carbazole
Base or fluorenyl.
Preferably, described pyrimidines is in following formula 1～20 shown in any one:
The present invention also provides for the application in an organic light emitting device of a kind of above-mentioned pyrimidines, described miazines chemical combination
Thing is used as electron transport material, hole mobile material or luminescent material in an organic light emitting device.
The present invention also provides for a kind of organic luminescent device, and this organic luminescent device includes pyrimidines described above.
Preferably, described organic luminescent device includes the first electrode, the second electrode and is arranged at described first electrode and
Organic matter layer between two electrodes；
Described organic matter layer comprises pyrimidines recited above.
Beneficial effects of the present invention
The present invention provides a kind of pyrimidines and application thereof and organic luminescent device, and this pyrimidines has formula
Structure shown in I, can be used for making OLED, and the technology such as existing display screen reaction rate is slow, power consumption, narrow viewing angle that solve are asked
Topic, additionally, also have Heat stability is good, luminous efficiency is high, and the advantages such as driving voltage is low, life-span length have and are applied to AMOLED
The prospect of industry.
Test result indicate that organic electroluminescence device prepared by the pyrimidines using the present invention to provide has
Higher luminous efficiency, lower driving voltage, luminous efficiency is up to 13～15cd/A, and driving voltage, up to 3.9V, is a kind of
Excellent OLED material.
Detailed description of the invention
In order to be further appreciated by the present invention, below in conjunction with embodiment, the preferred embodiment of the invention is described, but
Should be appreciated that these describe simply as to further illustrate the features and advantages of the present invention rather than to the claims in the present invention
Limit.
Present invention firstly provides a kind of pyrimidines, its general structure is as shown in formula I:
Wherein, X1、X2Independently selected from C or N；R1、R2、R3Independently selected from substituted or unsubstituted C6～C60 aryl,
The thick aryl of substituted or unsubstituted C10～C60, the heteroaryl of substituted or unsubstituted C5～C60.
Described X1、X2It is C or N time preferably different, i.e. works as X1During for C, X2For N, or X1During for N, X2For C.
Hetero atom in described heteroaryl is preferably N, O or S, more preferably N.
According to the present invention, in above-mentioned substituted aryl, substituted thick aryl and substituted heteroaryl, described substituent group is optional
From the alkyl of substituted or unsubstituted C1-C60, the aryl of substituted or unsubstituted C6-C60, substituted or unsubstituted C7-C60
Aralkyl, the cycloalkyl of substituted or unsubstituted C5-C60, the alkoxyl of substituted or unsubstituted C1-C60, replacement or do not take
The aryloxy group of the C6-C60 in generation, the arylamino of substituted or unsubstituted C6-C60, the alkyl of substituted or unsubstituted C1-C40
Amino, the silicyl of substituted or unsubstituted C1-C30, the heterocyclic radical of substituted or unsubstituted C5-C60.These substituent groups can
The substituent group being selected from this kind of group the most further replaces.
Described R1、R2、R3Preferably independently selected from the aryl, substituted or unsubstituted of substituted or unsubstituted C6～C20
The thick aryl of C10～C20, the heteroaryl of substituted or unsubstituted C5～C20, further preferably independently selected from pyridine radicals, imidazole radicals,
Thiazolyl, oxazolyl, pyrimidine radicals, quinolyl, pyrazinyl, triazine radical, carbazyl, phenyl, fluorenyl, naphthyl, xenyl, terphenyl
Base, anthryl or phenanthryl, more preferably independently selected from phenyl, xenyl, terphenyl, naphthyl, anthryl, phenanthryl, carbazyl or fluorenes
Base, most preferably independently selected from any one in following structure:
According to the present invention, described pyrimidines is preferably with in following formula 1～20 shown in any one:
It is enumerated above some concrete versions of pyrimidines of the present invention, but pyrimidine of the present invention
Compounds is not limited to these listed chemical constitutions, every based on structure shown in formula (I), R1、R2And R3For as above
The combination in any of the group limited all should be included.
The preparation method of pyrimidines of the present invention, including by formula II or the compound of formula III structure and formula
(IV) compound of structure carries out Suzuki coupling reaction, obtains the pyrimidines with formula I structure.Described reaction bar
The reaction condition that part is well known to those skilled in the art, the present invention there is no special restriction to this.
The compound of heretofore described formula II and formula III structure is prepared the most in accordance with the following methods:
Wherein, described R1、R2、R3The most same as above, do not repeat them here.
The present invention does not has particular/special requirement to the ratio of the reaction raw materials of above-mentioned reaction, with well known to those skilled in the art this
The conventional ratio of class reaction.The present invention does not has particular/special requirement to the condition of described reaction, knows with those skilled in the art
This type of reaction normal condition.
The present invention also provides for the application in an organic light emitting device of a kind of described pyrimidines, this pyrimidines
Can serve as electron transport layer materials, hole transport layer material or emitting layer material in an organic light emitting device.
The present invention also provides for a kind of organic luminescent device, including described pyrimidines.Described organic luminescent device is
Organic luminescent device well-known to those skilled in the art, organic luminescent device of the present invention preferably includes the first electricity
Pole, the second electrode and the organic matter layer being arranged between described first electrode and the second electrode；Described organic matter layer comprises described
Pyrimidines.Described organic matter layer preferably includes hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, sky
Barrier layer, cave, electron transfer layer and at least one of which in electron injecting layer, pyrimidines of the present invention is preferably as having
Electron transport layer materials in machine nitride layer.
The source of the raw material employed in following example is had no particular limits by the present invention, can be commercially available prod or
Preparation method well-known to those skilled in the art is used to prepare.
Embodiment 1: the synthesis of compound 1
(1) synthesis of compound 1-1: add 0.1mol 2,4,5,6-tetrachloro-pyrimidine, 0.2mol4-biphenyl in reaction bulb
Boric acid and the toluene of 1000mL, add potassium carbonate 200mmol and 1mmol catalyst Pd [P (C6H5)3]4, nitrogen is protected next time
Stream reaction 24 hours, adds distilled water 500ml, cold filtration, extracts with dichloromethane after having reacted, salt is washed, and has separated
Machine layer, rotation is evaporated off organic solvent, and thick product crosses post, then purifies with dichloromethane and ethyl alcohol recrystallization, obtains 39.4g compound
1-1, productivity 87%.
(2) synthesis of compound 1-2: in reaction bulb add 0.1mol compound 1-1,0.1mol4-pyridine boronic acid and
The toluene of 1000mL, adds potassium carbonate 200mmol and 1mmol catalyst Pd [P (C6H5)3]4, the lower back flow reaction 24 of nitrogen protection
Hour, adding distilled water 500ml, cold filtration after having reacted, extract with dichloromethane, salt is washed, and separates organic layer, and rotation is steamed
Removing organic solvent, thick product is crossed post, then is purified with dichloromethane and ethyl alcohol recrystallization, obtains 34.2g compound 1-2, productivity
69%.
(3) synthesis of compound 1: add 0.1mol compound 1-2,0.1mol 9,9-dimethyl-2-fluorenes in reaction bulb
Boric acid and the toluene of 1000mL, add potassium carbonate 200mmol and 1mmol catalyst Pd [P (C6H5)3]4, nitrogen is protected next time
Stream reaction 24 hours, adds distilled water 500ml, cold filtration, extracts with dichloromethane after having reacted, salt is washed, and has separated
Machine layer, rotation is evaporated off organic solvent, and thick product crosses post, then purifies with dichloromethane and ethyl alcohol recrystallization, obtains 36.0g compound
1, productivity 55%.
Mass spectrum m/z:653.83 (value of calculation: 653.81).Theoretical elemental content (%) C48H35N3: C, 88.18；H,5.40；
N, 6.43 actual measurement constituent content (%): C, 88.17；H,5.43；N,6.46.The above results confirms that obtaining product is target product.
Embodiment 2: the synthesis of compound 3
4-biphenylboronic acid in embodiment 1 step (1) is replaced with equimolar 1-naphthalenylboronic acid, and other steps are all with real
Execute example 1 identical, obtain 32.5g compound 3, productivity 54%.
Mass spectrum m/z:601.73 (value of calculation: 601.74).Theoretical elemental content (%) C44H31N3: C, 87.82；H,5.19；
N, 6.98 actual measurement constituent content (%): C, 87.83；H,5.17；N,7.00.The above results confirms that obtaining product is target product.
Embodiment 3: the synthesis of compound 6
4-biphenylboronic acid in embodiment 1 step (1) is replaced with equimolar 2-naphthalenylboronic acid, 9 in step (3),
9-dimethyl-2-fluorenes boric acid replaces with equimolar 4-biphenylboronic acid, and other steps are the most same as in Example 1, obtain 29.2gization
Compound 6, productivity 52%.
Mass spectrum m/z:561.69 (value of calculation: 561.67).Theoretical elemental content (%) C41H27N3: C, 87.67；H,4.85；
N, 7.48 actual measurement constituent content (%): C, 87.68；H,4.87；N,7.47.The above results confirms that obtaining product is target product.
Embodiment 4: the synthesis of compound 7
4-biphenylboronic acid in embodiment 1 step (1) is replaced with equimolar 9,9-dimethyl-2-fluorenes boric acid, step
(3) 9 in, 9-dimethyl-2-fluorenes boric acid replaces with equimolar 2-naphthalenylboronic acid, and other steps are the most same as in Example 1,
To 37.4g compound 7, productivity 56%.
Mass spectrum m/z:667.82 (value of calculation: 667.84).Theoretical elemental content (%) C49H57N3: C, 88.12；H,5.58；
N, 6.29 actual measurement constituent content (%): C, 88.12；H,5.57；N,6.28.The above results confirms that obtaining product is target product.
Embodiment 5: the synthesis of compound 10
By 9 in embodiment 1 step (3), 9-dimethyl-2-fluorenes boric acid replaces with equimolar 2-naphthalenylboronic acid, other
Step is the most same as in Example 1, obtains 31.7g compound 10, productivity 54%.
Mass spectrum m/z:587.73 (value of calculation: 587.71).Theoretical elemental content (%) C43H29N3: C, 87.88；H,4.97；
N, 7.15 actual measurement constituent content (%): C, 87.89；H,4.97；N,7.17.The above results confirms that obtaining product is target product.
Embodiment 6: the synthesis of compound 11
4-pyridine boronic acid in embodiment 1 step (2) is replaced with equimolar 3-pyridine boronic acid, and other steps are all with real
Execute example 1 identical, obtain 34.7g compound 11, productivity 53%.
Mass spectrum m/z:653.82 (value of calculation: 653.81).Theoretical elemental content (%) C48H35N3: C, 88.18；H,5.40；
N, 6.43 actual measurement constituent content (%): C, 88.17；H,5.42；N,6.46.The above results confirms that obtaining product is target product.
Embodiment 7: the synthesis of compound 13
4-pyridine boronic acid in embodiment 2 step (2) is replaced with equimolar 3-pyridine boronic acid, and other steps are all with real
Execute example 2 identical, obtain 30.7g compound 13, productivity 51%.
Mass spectrum m/z:601.73 (value of calculation: 601.74).Theoretical elemental content (%) C44H31N3: C, 87.82；H,5.19；
N, 6.98 actual measurement constituent content (%): C, 87.83；H,5.17；N,7.00.The above results confirms that obtaining product is target product.
Embodiment 8: the synthesis of compound 16
4-pyridine boronic acid in embodiment 3 step (2) is replaced with equimolar 3-pyridine boronic acid, and other steps are all with real
Execute example 3 identical, obtain 30.3g compound 16, productivity 54%.
Mass spectrum m/z:561.69 (value of calculation: 561.67).Theoretical elemental content (%) C41H27N3: C, 87.67；H,4.85；
N, 7.48 actual measurement constituent content (%): C, 87.67；H,4.86；N,7.47.The above results confirms that obtaining product is target product.
Embodiment 9: the synthesis of compound 17
4-pyridine boronic acid in embodiment 4 step (2) is replaced with equimolar 3-pyridine boronic acid, and other steps are all with real
Execute example 4 identical, obtain 33.4g compound 17, productivity 50%.
Mass spectrum m/z:667.82 (value of calculation: 667.84).Theoretical elemental content (%) C49H57N3: C, 88.12；H,5.58；
N, 6.29 actual measurement constituent content (%): C, 88.13；H,5.57；N,6.28.The above results confirms that obtaining product is target product.
Embodiment 10: the synthesis of compound 20
4-pyridine boronic acid in embodiment 5 step (2) is replaced with equimolar 3-pyridine boronic acid, and other steps are all with real
Execute example 5 identical, obtain 30.0g compound 20, productivity 51%.
Mass spectrum m/z:587.73 (value of calculation: 587.71).Theoretical elemental content (%) C43H29N3: C, 87.88；H,4.97；
N, 7.15 actual measurement constituent content (%): C, 87.89；H,4.98；N,7.17.The above results confirms that obtaining product is target product.
Contrast Application Example:
By transparent anode electrode ito substrate ultrasonic cleaning 10 minutes in isopropanol, and expose 30 minutes under ultraviolet light,
Process 8 minutes with plasma subsequently.Ito substrate after processing subsequently puts into evaporated device.First the NPB of one layer of 35nm it is deposited with
As the evaporation of hole transmission layer, followed by luminescent layer, mixing evaporation, CBP, and the Ir (piq) of 5%3, it is deposited with 30nm subsequently
Alq3 as electron transfer layer, be deposited with 1nmLiF the most again, be deposited with the metal Al of 150nm subsequently.
Application Example 1
By transparent anode electrode ito substrate ultrasonic cleaning 10 minutes in isopropanol, and expose 30 minutes under ultraviolet light,
Process 8 minutes with plasma subsequently.Ito substrate after processing subsequently puts into evaporated device.First the NPB of one layer of 35nm it is deposited with
As the evaporation of hole transmission layer, followed by luminescent layer, mixing evaporation compound CBP, and the Ir (piq) of 5%3, steam subsequently
The compound 1 of plating 30nm, as electron transfer layer, is deposited with 1nmLiF the most again, is deposited with the metal Al of 150nm subsequently.
Application Example 2
Change the compound 1 in Application Example into compound 11.
Application Example 3
Change the compound 1 in Application Example into compound 3.
Application Example 4
Change the compound 1 in Application Example into compound 6.
Wherein:
OLED is produced as follows:
Contrast Application Example: ITO/NPB/CBP:Ir (piq)3/Alq3/LiF/Al；
Application Example 1:ITO/NPB/CBP:Ir (piq)3/ compound 1/LiF/Al；
Application Example 2:ITO/NPB/CBP:Ir (piq)3/ compound 11/LiF/Al；
Application Example 3:ITO/NPB/CBP:Ir (piq)3/ compound 3/LiF/Al；
Application Example 4:ITO/NPB/CBP:Ir (piq)3/ compound 6/LiF/Al.
Under 1000nits, OLED result is as follows:
| Device | Cd/A | Driver Voltage |
| Contrast Application Example | 8cd/A | 4.7V |
| Application Example 1 | 14cd/A | 3.9V |
| Application Example 2 | 13cd/A | 4.2V |
| Application Example 3 | 14cd/A | 4.1V |
| Application Example 4 | 15cd/A | 4.3V |
It can be seen that organic electroluminescence device prepared by the pyrimidines using the present invention to provide, have higher
Luminous efficiency, lower driving voltage, luminous efficiency is up to 13～15cd/A, and driving voltage, up to 3.9V, is a kind of excellent
OLED material.
Obviously, the explanation of above example is only intended to help to understand method and the core concept thereof of the present invention.Should refer to
Go out, for the those of ordinary skill of described technical field, under the premise without departing from the principles of the invention, it is also possible to this
Bright carrying out some improvement and modification, these improve and modify in the protection domain also falling into the claims in the present invention.
Claims (9)
1. a pyrimidines, shown in its general structure such as formula (I):
Wherein, X1、X2Independently selected from C or N；
R1、R2、R3Independently selected from the aryl of substituted or unsubstituted C6～C60, the thick virtue of substituted or unsubstituted C10～C60
Base, the heteroaryl of substituted or unsubstituted C5～C60.
Pyrimidines the most according to claim 1, it is characterised in that as shown in formula (I-1) or formula (I-2):
Wherein, R1、R2、R3Aryl, substituted or unsubstituted C10～C60 independently selected from substituted or unsubstituted C6～C60
Thick aryl, the heteroaryl of substituted or unsubstituted C5～C60.
Pyrimidines the most according to claim 1, it is characterised in that described R1、R2、R3Independently selected from replace or
The aryl of unsubstituted C6～C20, the thick aryl of substituted or unsubstituted C10～C20, substituted or unsubstituted C5～C20
Heteroaryl.
Pyrimidines the most according to claim 1, it is characterised in that the hetero atom in described heteroaryl is N.
Pyrimidines the most according to claim 1, it is characterised in that described R1、R2、R3Independently selected from phenyl, connection
Phenyl, terphenyl, naphthyl, anthryl, phenanthryl, carbazyl or fluorenyl.
Pyrimidines the most according to claim 1, it is characterised in that in following formula 1～20 shown in any one:
。
7. pyrimidines application in an organic light emitting device described in claim 1～6 any one, it is characterised in that
Described pyrimidines is used as electron transport material, hole mobile material or luminescent material in an organic light emitting device.
8. an organic luminescent device, it is characterised in that include the pyrimidines described in any one of claim 1～6.
Organic luminescent device the most according to claim 8, it is characterised in that described organic luminescent device includes the first electricity
Pole, the second electrode and the organic matter layer being arranged between described first electrode and the second electrode；
Described organic matter layer comprises the pyrimidines described in claim 1～6 any one.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019049965A1 (en) * | 2017-09-11 | 2019-03-14 | 保土谷化学工業株式会社 | Compound having pyrimidine ring structure and organic electroluminescent element |
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| WO2019049965A1 (en) * | 2017-09-11 | 2019-03-14 | 保土谷化学工業株式会社 | Compound having pyrimidine ring structure and organic electroluminescent element |
| CN111094264A (en) * | 2017-09-11 | 2020-05-01 | 保土谷化学工业株式会社 | Compound with pyrimidine ring structure and organic electroluminescence device |
| KR20200051651A (en) * | 2017-09-11 | 2020-05-13 | 호도가야 가가쿠 고교 가부시키가이샤 | A compound having a pyrimidine ring structure and an organic electroluminescence device |
| JPWO2019049965A1 (en) * | 2017-09-11 | 2020-08-20 | 保土谷化学工業株式会社 | Compound having pyrimidine ring structure and organic electroluminescence device |
| JP7159173B2 (en) | 2017-09-11 | 2022-10-24 | 保土谷化学工業株式会社 | Compound having pyrimidine ring structure and organic electroluminescence device |
| KR102603365B1 (en) * | 2017-09-11 | 2023-11-16 | 호도가야 가가쿠 고교 가부시키가이샤 | Compounds having a pyrimidine ring structure and organic electroluminescence devices |
| US12221430B2 (en) | 2017-09-11 | 2025-02-11 | Hodogaya Chemical Co., Ltd. | Compound having pyrimidine ring structure and organic electroluminescence device |
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