CN108558874A - A kind of aryl amine derivatives and its organic electroluminescence device containing phenanthroline - Google Patents

A kind of aryl amine derivatives and its organic electroluminescence device containing phenanthroline Download PDF

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CN108558874A
CN108558874A CN201810476675.1A CN201810476675A CN108558874A CN 108558874 A CN108558874 A CN 108558874A CN 201810476675 A CN201810476675 A CN 201810476675A CN 108558874 A CN108558874 A CN 108558874A
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substituted
unsubstituted
aryl
amine derivatives
hydrogen
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周雯庭
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The present invention provides a kind of aryl amine derivatives and its organic electroluminescence device containing phenanthroline, is related to organic optoelectronic materials technology.Such compounds process for production thereof is simple, raw material is easy to get, with high hole mobility, and stability and good film-forming property, also there is the highest occupied molecular orbital energy level between hole transmission layer and luminescent layer, and there is high T1 values and refractive index, it is applied in OLED device as luminous auxiliary layer and hole transmission layer, the equalizing charge in luminescent layer may be implemented, to significantly improve the luminous efficiency, heat resistance and service life of device, the driving voltage that device can also be reduced simultaneously, is the OLED material of a kind of function admirable.

Description

A kind of aryl amine derivatives and its organic electroluminescence device containing phenanthroline
Technical field
The present invention relates to organic photoelectrical material technical fields, and in particular to a kind of aryl amine derivatives containing phenanthroline and Its organic electroluminescence device.
Background technology
Organic Light Emitting Diode (OLED) is Dual Implantations type luminescent device, be by anode, cathode and anode and cathode it Between one layer or more of organic thin film layer constitute, using electroluminescent physical mechanism, apply voltage between two electrodes, electricity Son is injected into light-emitting zone from cathode side, and hole is injected into light-emitting zone from anode side, and the two is combined into excite shape State sends out light when excited state restores to ground state, and electric energy is converted into the luminous energy of organic semiconducting materials molecule, tool Have self luminous characteristic, be not necessarily to backlight, have high brightness, high contrast, fine definition, wide viewing angle, wide colour gamut, low-power consumption, The advantages that wide temperature, luminous efficiency are high, the reaction time is short, transparent, flexible has good application prospect.
OLED material is divided into luminescent material, hole mobile material, electron transport material etc..Wherein, hole mobile material is logical Often with there is low highest occupied molecular orbital (HOMO) value, most of to have low T1 values, what is generated in luminescent layer as a result, swashs Sub (exciton) is diffused into hole transport bed boundary or hole transmission layer side, eventually leads to shining in luminescent layer inner boundary Or the charge in luminescent layer is unbalanced (charg eunbalance), to shine on the interface of hole transmission layer, makes to have The excitation purity and efficiency of electrical-mechanical element are lower, and the service life shortens.
Therefore, there is an urgent need to develop going out other than with These characteristics, also there is the hole of the high mobility for hole Transmission material.
Invention content
In view of the above-mentioned problems existing in the prior art, the present invention provide a kind of aryl amine derivatives containing phenanthroline and its Organic electroluminescence device.
The present invention provides a kind of aryl amine derivatives containing phenanthroline, shown in structural formula such as formula (I)：
Wherein, R1、R2、R3、R4、R5Independently selected from hydrogen, halogen, the substituted or unsubstituted alkyl of C1~C12, C6~C30 The substituted or unsubstituted heteroaryl of substituted or unsubstituted aryl, C3~C30；L is selected from singly-bound, C6~C30 substitutions or unsubstituted Divalent aryl, the substituted or unsubstituted divalent heteroaryl radicals of C3~C30；Ar1、Ar2Replace independently selected from C6~C60 or does not take The substituted or unsubstituted heteroaryl of aryl, C3~C60 or Ar in generation1With Ar2It is interconnected to nitrogenous five-ring heterocycles.
Preferably, the aryl amine derivatives containing phenanthroline have structure shown in logical formula (II) or (III)：
Wherein, R1、R2、R3、R4、R5Independently selected from hydrogen, fluorine atom, the substituted or unsubstituted alkyl of C1~C4, C6~C30 The substituted or unsubstituted heteroaryl of substituted or unsubstituted aryl, C3~C30；L is selected from singly-bound, C6~C30 substitutions or unsubstituted Divalent aryl, the substituted or unsubstituted divalent heteroaryl radicals of C3~C30；Z1、Z2、Z3、Z4、Z5、Z6、Z7、Z8、Z9、Z10Independently select From hydrogen, deuterium, cyano, halogen, the substituted or unsubstituted alkyl of C1~C4, the substituted or unsubstituted alkoxies of C1~C4, C6~C30 The substituted or unsubstituted heteroaryl of substituted or unsubstituted aryl, C3~C60 or Z1、Z2、Z3、Z4、Z5、Z6、Z7、Z8、Z9、Z10 Two substituent groups of middle arbitrary neighborhood can be connected to form ring.
Preferably, the L is selected from singly-bound or following group：
Wherein, Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8Independently selected from hydrogen, deuterium, cyano, fluorine atom, methyl, ethyl, positive third Base, isopropyl, normal-butyl, sec-butyl, isobutyl group, tertiary butyl.
Preferably, the aryl amine derivatives containing phenanthroline have structure shown in following general formula：
Wherein, R1、R2、R3、R4、R5Independently selected from hydrogen, fluorine atom, the substituted or unsubstituted alkyl of C1~C4, C6~C30 The substituted or unsubstituted heteroaryl of substituted or unsubstituted aryl, C3~C30；Z1、Z2、Z3、Z4、Z5、Z6、Z7、Z8、Z9、Z10It is independent Ground is selected from hydrogen, deuterium, cyano, halogen, the substituted or unsubstituted alkyl of C1~C4, the substituted or unsubstituted alkoxies of C1~C4, C6 The substituted or unsubstituted aryl of~C30, the substituted or unsubstituted heteroaryls of C3~C60 or Z1、Z2、Z3、Z4、Z5、Z6、Z7、Z8、 Z9、Z10Two substituent groups of middle arbitrary neighborhood can be connected to form ring；Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8Independently selected from hydrogen, Deuterium, cyano, fluorine atom, methyl, ethyl, n-propyl, isopropyl, normal-butyl, sec-butyl, isobutyl group, tertiary butyl.
Preferably, the R1、R2、R3、R4、R5Independently selected from hydrogen, fluorine atom, methyl or following group：
Wherein, X1、X2、X3、X4、X5、X6、X7、X8、X9Independently selected from hydrogen, deuterium, fluorine atom, cyano, methyl, ethyl, just Propyl, isopropyl, normal-butyl, isobutyl group, tertiary butyl, sec-butyl, methoxyl group, difluoromethyl, trifluoromethyl.
Most preferably, the aryl amine derivatives containing phenanthroline are arbitrary in HT1~HT104 as follows It is a kind of：
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device include cathode, anode and The one or more organic matter layers being placed between the cathode and the anode；Contain neighbour containing described in the organic matter layer The aryl amine derivatives of ferrosin.
Preferably, the auxiliary layer that shines is contained in the organic matter layer；Contain containing described in the luminous auxiliary layer There are the aryl amine derivatives of phenanthroline.
It is furthermore preferred that containing hole transmission layer simultaneously in the organic matter layer；Containing in the hole transmission layer The aryl amine derivatives containing phenanthroline stated.
Beneficial effects of the present invention：
Aryl amine derivatives provided by the invention containing phenanthroline have high hole mobility, and compound is steady Fixed, film forming might as well.Such compound has the occupied molecular orbital energy of the highest between hole transmission layer and luminescent layer Grade, and there is high T1 values and refractive index, it is applied in OLED device as luminous auxiliary layer and hole transmission layer, can realizes hair Equalizing charge in photosphere shines, moreover it is possible to improve the luminous efficiency, heat resistance and service life of OLED device, together in luminescent layer When reduce OLED device driving voltage, be the OLED material of a kind of function admirable.
Specific implementation mode
Present invention firstly provides a kind of aryl amine derivatives containing phenanthroline, structure formula (I) is as follows：
Wherein, R1、R2、R3、R4、R5Independently selected from hydrogen, halogen, the substituted or unsubstituted alkyl of C1~C12, C6~C30 The substituted or unsubstituted heteroaryl of substituted or unsubstituted aryl, C3~C30；L is selected from singly-bound, C6~C30 substitutions or unsubstituted Divalent aryl, the substituted or unsubstituted divalent heteroaryl radicals of C3~C30；Ar1、Ar2Replace independently selected from C6~C60 or does not take The substituted or unsubstituted heteroaryl of aryl, C3~C60 or Ar in generation1With Ar2It is interconnected to nitrogenous five-ring heterocycles.
Preferably, the aryl amine derivatives containing phenanthroline have structure shown in logical formula (II) or (III)：
Wherein, R1、R2、R3、R4、R5Independently selected from hydrogen, fluorine atom, the substituted or unsubstituted alkyl of C1~C4, C6~C30 The substituted or unsubstituted heteroaryl of substituted or unsubstituted aryl, C3~C30；L is selected from singly-bound, C6~C30 substitutions or unsubstituted Divalent aryl, the substituted or unsubstituted divalent heteroaryl radicals of C3~C30；Z1、Z2、Z3、Z4、Z5、Z6、Z7、Z8、Z9、Z10Independently select From hydrogen, deuterium, cyano, halogen, the substituted or unsubstituted alkyl of C1~C4, the substituted or unsubstituted alkoxies of C1~C4, C6~C30 The substituted or unsubstituted heteroaryl of substituted or unsubstituted aryl, C3~C60 or Z1、Z2、Z3、Z4、Z5、Z6、Z7、Z8、Z9、Z10 Two substituent groups of middle arbitrary neighborhood can be connected to form ring.
Preferably, the L is selected from singly-bound or following group：
Wherein, Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8Independently selected from hydrogen, deuterium, cyano, fluorine atom, methyl, ethyl, positive third Base, isopropyl, normal-butyl, sec-butyl, isobutyl group, tertiary butyl.
Preferably, the aryl amine derivatives containing phenanthroline have structure shown in following general formula：
Wherein, R1、R2、R3、R4、R5Independently selected from hydrogen, fluorine atom, the substituted or unsubstituted alkyl of C1~C4, C6~C30 The substituted or unsubstituted heteroaryl of substituted or unsubstituted aryl, C3~C30；Z1、Z2、Z3、Z4、Z5、Z6、Z7、Z8、Z9、Z10It is independent Ground is selected from hydrogen, deuterium, cyano, halogen, the substituted or unsubstituted alkyl of C1~C4, the substituted or unsubstituted alkoxies of C1~C4, C6 The substituted or unsubstituted aryl of~C30, the substituted or unsubstituted heteroaryls of C3~C60 or Z1、Z2、Z3、Z4、Z5、Z6、Z7、Z8、 Z9、Z10Two substituent groups of middle arbitrary neighborhood can be connected to form ring；Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8Independently selected from hydrogen, Deuterium, cyano, fluorine atom, methyl, ethyl, n-propyl, isopropyl, normal-butyl, sec-butyl, isobutyl group, tertiary butyl.
Preferably, the R1、R2、R3、R4、R5Independently selected from hydrogen, fluorine atom, methyl or following group：
Wherein, X1、X2、X3、X4、X5、X6、X7、X8、X9Independently selected from hydrogen, deuterium, fluorine atom, cyano, methyl, ethyl, just Propyl, isopropyl, normal-butyl, isobutyl group, tertiary butyl, sec-butyl, methoxyl group, difluoromethyl, trifluoromethyl.
Aryl of the present invention refer to aromatic hydrocarbon molecule an aromatic core carbon on remove a hydrogen atom after, remaining group General name, can be monocyclic aryl or fused ring aryl, such as can be selected from phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthrene Base, pyrenyl, fluorenyl or benzo phenanthryl etc., but not limited to this.
Heteroaryl of the present invention refers to the group that one or more of aryl aromatic core carbon is replaced by hetero atom General name, the hetero atom include but not limited to oxygen, sulphur or nitrogen-atoms, and the heteroaryl can be bicyclic heteroaryl or condensed ring heteroaryl Base, such as pyridyl group, quinolyl, carbazyl, thienyl, benzothienyl, furyl, benzofuranyl, pyrimidine can be selected from Base, benzo pyrimidine radicals, imidazole radicals or benzimidazolyl etc., but not limited to this.
Divalent aryl of the present invention refer to aromatic hydrocarbon molecule two aromatic core carbon on respectively remove a hydrogen atom after, be left Bivalent group general name, can be valentbivalent monocyclic aryl or divalent fused ring aryl, such as can be selected from phenylene, sub- biphenyl Base, sub- terphenyl, naphthylene, anthrylene, phenanthrylene, sub- pyrenyl, fluorenylidene or sub- benzo phenanthryl etc., but not limited to this.
Divalent heteroaryl radical of the present invention refers to that one or more of divalent aryl aromatic core carbon is replaced to obtain by hetero atom Group general name, the hetero atom includes but not limited to oxygen, sulphur or nitrogen-atoms, and the divalent heteroaryl radical can be valentbivalent monocyclic Heteroaryl or divalent fused ring heteroaryl, such as sub-pyridyl group, sub- quinolyl, sub- carbazyl, sub- thienyl, sub- benzo can be selected from Thienyl, furylidene, sub- benzofuranyl, sub- pyrimidine radicals, sub- benzo pyrimidine radicals, sub- imidazole radicals or sub- benzimidazolyl etc., But not limited to this.
Alkyl of the present invention refers to alkyl made of removing a hydrogen atom in alkane molecule, can be straight chain alkane Base, branched alkyl, naphthenic base, such as methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, uncle can be selected from Butyl, amyl, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Alkoxy of the present invention refers to-O- alkyl, wherein the alkyl is as previously defined.
Nitrogenous five-ring heterocycles of the present invention refer to substituted or unsubstituted carbazole.
Specifically, the aryl amine derivatives containing phenanthroline are any one in HT1~HT104 as follows Kind：
Some specific constructive forms of the aryl amine derivatives of the present invention containing phenanthroline, but this is enumerated above Invention is not limited to these listed chemical constitutions, and every based on structure shown in listed general formula, substituent group is as above is limited Fixed group should be all included.
The preparation method of aryl amine derivatives of the present invention containing phenanthroline can be prepared by following synthetic route It obtains：
Wherein, R1、R2、R3、R4、R5Independently selected from hydrogen, halogen, the substituted or unsubstituted alkyl of C1~C12, C6~C30 The substituted or unsubstituted heteroaryl of substituted or unsubstituted aryl, C3~C30；L is selected from singly-bound, C6~C30 substitutions or unsubstituted Divalent aryl, the substituted or unsubstituted divalent heteroaryl radicals of C3~C30；Ar1、Ar2Replace independently selected from C6~C60 or does not take The substituted or unsubstituted heteroaryl of aryl, C3~C60 or Ar in generation1With Ar2It is interconnected to nitrogenous five-ring heterocycles.
First, with 2- chloro- 1,3-PDs annulation occurs for aminoquinoline compounds (compound A), obtains intermediate B；Then intermediate B is reacted with connection pinacol borate, generates intermediate C；It is anti-that with I-L-Br Suzuki occurs for intermediate C again It answers, obtains intermediate D；Finally, intermediate D with contain the Ar1And Ar2Aromatic amine compound pass through Buchwald-Hartwig Coupling reaction, you can obtain target compound (I).
The present invention does not have special limitation, use well-known to those skilled in the art the above-mentioned reaction condition respectively reacted Reaction condition, the preparation method is simple, and raw material is easy to get.
The present invention further provides a kind of organic electroluminescence device, the organic electroluminescence device include cathode, Anode and the one or more organic matter layers being placed between the cathode and the anode；Contain the present invention in the organic matter layer The aryl amine derivatives containing phenanthroline preferably comprise hole injection layer, hole transmission layer, hair in the organic matter layer At least one layer in light auxiliary layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer；Preferably, described organic Containing the auxiliary layer that shines in nitride layer, the luminous auxiliary layer contains neighbour between luminescent layer and anode, and containing described The aryl amine derivatives of ferrosin；Preferably, contain hole transmission layer in the organic matter layer simultaneously, the hole transmission layer is located at It shines between auxiliary layer and anode, and contains the aryl amine derivatives containing phenanthroline.
According to the present invention, the device architecture of use is preferred, Ke Yiwei：Transparent glass is as anode；4,4', 4 "-three [2- naphthylphenyls amino] triphenylamine (2-TNATA) is used as hole injection layer；N, N'- diphenyl-N, N'- (1- naphthalenes) -1, 1'- biphenyl -4,4'- diamines (NPB) or the compounds of this invention (HT1~HT104) are used as hole transmission layer；The compounds of this invention (HT1~HT104) is as the auxiliary layer that shines；(9- carbazoles) biphenyl of 4,4'- bis- (CBP) and two (1- phenyl-isoquinolin) (levulinics Ketone) close iridium ((piq)2Ir (acac)) with 95:The mixture of 5 weight ratio is as luminescent layer；Bis- (2- methyl -8-hydroxyquinoline - N1, O8)-(1,1'- biphenyl -4- hydroxyls) aluminium (BAlq) be used as hole blocking layer；8-hydroxyquinoline aluminium (Alq3) passed as electronics Defeated layer；LiF is as electron injecting layer；Al is as cathode.
The organic electroluminescence device can be used for the application neck such as flat-panel monitor, lighting source, direction board, signal lamp Domain.
By following embodiment, the present invention, but so as not to the limitation present invention are more fully explained.In the base of the description On plinth, those of ordinary skill in the art will without creative efforts, in disclosed entire scope Implement the present invention and prepares other compounds according to the present invention.
The present invention is not particularly limited the raw material sources employed in following embodiment, for commercial product or can adopt It is prepared with preparation method well-known to those skilled in the art.
Embodiment 1：The preparation of compound HT1
Under argon atmospher, by 12.96g (50mmol) 3- bromines phenanthroline, 16.07g (50mmol) two (4- xenyls) amine, 9.61g (100mmol) sodium tert-butoxide is dissolved in 500ml dehydrated toluenes, is added with stirring 0.22g (1mmol) palladium, 0.26g (1mmol) triphenylphosphine reacts 8 hours at 80 DEG C.It after cooling, is filtered by diatomite/silica gel funnel, filtrate passes through decompression Distillation removal organic solvent, it is residue obtained to be recrystallized in toluene, it is dry, you can to obtain 22.23g (44.5mmol) compound HT1, yield 89%.Mass spectrum m/z：500.93 (calculated values：499.62).Theoretical elemental content (%) C36H25N3：C,86.55； H,5.04；N,8.41.Survey constituent content (%)：C,86.52；H,5.01；N,8.53.The above results confirm that it is mesh to obtain product Mark product.
Embodiment 2：The preparation of compound HT5
The preparation of compound M-1：Under argon atmospher, by 4.91g (50mmol) aniline -2,3,4,5,6-d5,19.76g (50mmol) 2- bromo- 9,9 '-spiral shell, two fluorenes, 9.60g (100mmol) sodium tert-butoxide are dissolved in 500ml dehydrated toluenes, are added with stirring 0.23g (1mmol) palladium, 0.20g (1mmol) triphenylphosphine, react 8 hours at 80 DEG C.After cooling, by diatomite/ Silica gel funnel filters, and filtrate removes organic solvent by vacuum distillation, residue obtained to be recrystallized in toluene, dry, you can To 17.53g (42.50mmol) compounds M-1.
The preparation of compound HT5：Two (4- xenyls) amine are replaced with to the intermediate M-1 of equimolar amounts, other steps It is same as Example 1, you can to obtain compound HT5.Mass spectrum m/z：592.11 (calculated values：590.74).Theoretical elemental content (%) C43H22D5N3：C,87.43；H,5.46；N,7.11.Survey constituent content (%)：C,87.41；H,5.44；N,7.16.On Stating result confirms that it is target product to obtain product.
Embodiment 3：The preparation of compound HT20
The preparation of compound N -1：The bromo- 8- aminoquinolines of 22.31g (100mmol) 3-, 11.05g (100mmol) 2- is chloro- 1,3- propylene glycol, 1.12g (5mmol) palladium, 1.21g (5mmol) 2,4,6- collidines, 1.14g (10mmol) trifluoro second Acid is warming up to 150 DEG C under oxygen atmosphere (1atm), reacts 12 hours.After reaction, it filters, filtrate concentration passes through column layer Analysis method purifies, and obtains compound N -1.
The preparation of intermediate B -1：By 11.74g (40mmol) compound N -1,8.72g (40mmol) 3- methylphenylboronic acid frequencies Which alcohol ester, 0.62g (0.53mmol) tetrakis triphenylphosphine palladium, 115ml toluene and 56ml aqueous sodium carbonates (2M) put into flask In, back flow reaction 8 hours is cooled to room temperature, is extracted with toluene, organic phase saturated common salt water washing, dry, passes through column chromatography Method purifies, and finally obtains intermediate B -1 (9.14g, 30.0mmol).
The preparation of compound M-2：The 3- aminobphenyls of equimolar amounts are replaced with by aniline -2,3,4,5,6-d5, by 2- Bromo- 9,9 '-spiral shell, two fluorenes is replaced with the bromo- dibenzo of 9- [2,1-B] furans of equimolar amounts, other steps in embodiment 2 Preparing for compound M-1 is identical, you can obtains compound M-2.
The preparation of compound HT20：3- bromine phenanthrolines are substituted for the intermediate B -1 of equimolar amounts, by two (4- biphenyl Base) amine is replaced with the compound M-2 of equimolar amounts, and other steps are same as Example 1, you can obtain compound HT20. Mass spectrum m/z：654.87 (calculated values：653.79).Theoretical elemental content (%) C47H31N3O：C,86.35；H,4.78；N,6.43； O,2.45.Survey constituent content (%)：C,86.37；H,4.76；N,6.45；O,2.43.The above results confirm that it is mesh to obtain product Mark product.
Embodiment 4：The preparation of compound HT46
The preparation of intermediate B -2：By 3- methylphenylboronic acid pinacol esters be replaced with equimolar amounts 1- naphthalene boronic acids frequency which Alcohol ester, other steps are identical as the preparation method of intermediate B -1 in embodiment 3, you can obtain intermediate B -2.
The preparation of intermediate C-1：10.22g (30mmol) intermediate B -2,9.33g (36mmol) are joined into boric acid pinacol Ester, 0.66g (0.9mmol) [bis- (diphenylphosphino) ferrocene of 1,1'-] palladium chlorides and the dissolving of 8.84g (90mmol) potassium acetate In 197ml toluene, back flow reaction 12 hours, after being cooled to room temperature, cross diatom soil hopper, remove solvent, institute under an argon It obtains residue to recrystallize in heptane, filters out crystal and drying, obtain intermediate C-1 (10.25g, 23.7mmol).
The preparation of intermediate D-1：The bromo- 1,3- bis- of 8.65g (20mmol) intermediates C-1,6.38g (20mmol) 2- is fluoro- 5- iodobenzenes, 0.47g (0.4mmol) tetrakis triphenylphosphine palladium, 57ml toluene, aqueous sodium carbonate (2M, 28ml) are added in flask, Back flow reaction 8 hours, is cooled to room temperature, is extracted with toluene, organic phase saturated common salt water washing, dry, passes through column chromatography Purifying, obtains intermediate D-1 (8.06g, 16.2mmol).
The preparation of compound HT46：3- bromine phenanthrolines are substituted for the intermediate D-1 of equimolar amounts, by two (4- biphenyl Base) amine is replaced with 3, the 6- dimethyl -9H- carbazoles of equimolar amounts, and other steps are same as Example 1, you can are changed Close object HT46.Mass spectrum m/z：612.83 (calculated values：611.70).Theoretical elemental content (%) C42H27F2N3：C,82.47；H, 4.45；F,6.21；N,6.87.Survey constituent content (%)：C,82.49；H,4.42；F,6.24；N,6.84.The above results confirm Acquisition product is target product.
Embodiment 5：The preparation of compound HT59
The preparation of compound N -2：The bromo- 8- aminoquinolines of 6- that the bromo- 8- aminoquinolines of 3- are replaced with equimolar amounts, His step in embodiment 3 intermediate N 1 prepare it is identical, you can obtain intermediate N 2.
The preparation of intermediate B -3：Compound N -1 is replaced with to the compound N -2 of equimolar amounts, by 3- methylphenylboronic acids Pinacol ester is replaced with the phenyl boric acid of equimolar amounts, preparation method phase of other steps with intermediate B -1 in embodiment 3 Together, you can obtain intermediate B -3.
The preparation of intermediate C-2：Intermediate B -2 is replaced with to the intermediate B -3 of equimolar amounts, other steps with reality The preparation method for applying intermediate C-1 in example 4 is identical, you can obtains intermediate C-2.
The preparation of intermediate D-2：Intermediate C-1 is replaced with to the intermediate C-2 of equimolar amounts, by bromo- 1, the 3- of 2- bis- Fluoro- 5- iodobenzenes be replaced with equimolar amounts to bromo-iodobenzene, preparation method of other steps with intermediate D-1 in embodiment 4 It is identical, you can to obtain intermediate D-2.
The preparation of compound HT59：3- bromine phenanthrolines are substituted for the intermediate D-2 of equimolar amounts, by two (4- biphenyl Base) amine is replaced with 3, the 6- diphenyl -9H- carbazoles of equimolar amounts, and other steps are same as Example 1, you can are changed Close object HT59.Mass spectrum m/z：550.56 (calculated values：649.80).Theoretical elemental content (%) C48H31N3：C,88.72；H,4.81； N,6.47.Survey constituent content (%)：C,88.70；H,4.83；N,6.49.The above results confirm that it is target product to obtain product.
Embodiment 6：The preparation of compound HT83
The preparation of compound M-3：It is replaced with the 2- naphthylamines of equimolar amounts by aniline -2,3,4,5,6-d5, by 2- bromo- 9, 9 '-spiral shell, two fluorenes is replaced with the 5- bromobenzenes of equimolar amounts, and simultaneously [B] naphtho- [1,2-D] thiophene, other steps are changed with embodiment 2 It is identical to close preparing for object M-1, you can obtain compound M-3.
The preparation of compound N -3：The bromo- 8- aminoquinolines of 4- that the bromo- 8- aminoquinolines of 3- are replaced with equimolar amounts, His step in embodiment 3 intermediate N 1 prepare it is identical, you can obtain intermediate N 3.
The preparation of intermediate B -4：Compound N -1 is replaced with to the compound N -3 of equimolar amounts, by 3- methylphenylboronic acids Pinacol ester is replaced with 3- bases -9- phenyl-carbazole pinacol ester of equimolar amounts, other steps with it is intermediate in embodiment 3 The preparation method of body B-1 is identical, you can obtains intermediate B -4.
The preparation of compound HT83：3- bromine phenanthrolines are substituted for the intermediate B -4 of equimolar amounts, by two (4- biphenyl Base) amine is replaced with the compound M-3 of equimolar amounts, and other steps are same as Example 1, you can obtain compound HT83. Mass spectrum m/z：796.13 (calculated values：794.98).Theoretical elemental content (%) C56H34N4S：C,84.61；H,4.31；N,7.05； S,4.03.Survey constituent content (%)：C,84.63；H,4.28；N,7.07；S,4.05.The above results confirm that it is mesh to obtain product Mark product.
Embodiment 7：The preparation of compound HT87
The preparation of intermediate B -5：Compound N -1 is replaced with to the compound N -3 of equimolar amounts, by 3- methylphenylboronic acids Pinacol ester is replaced with the 3- cyanophenylboronic acid pinacol esters of equimolar amounts, other steps with intermediate B -1 in embodiment 3 Preparation method it is identical, you can obtain intermediate B -5.
The preparation of intermediate C-3：Intermediate B -2 is replaced with to the intermediate B -5 of equimolar amounts, other steps with reality The preparation method for applying intermediate C-1 in example 4 is identical, you can obtains intermediate C-3.
The preparation of intermediate D-3：Intermediate C-1 is replaced with to the intermediate C-3 of equimolar amounts, by bromo- 1, the 3- of 2- bis- The iodo- 4 '-bromo biphenyls of 4- that fluoro- 5- iodobenzenes are replaced with equimolar amounts, system of other steps with intermediate D-1 in embodiment 4 Preparation Method is identical, you can obtains intermediate D-3.
The preparation of compound HT87：3- bromine phenanthrolines are substituted for the intermediate D-3 of equimolar amounts, by two (4- biphenyl Base) amine is replaced with 4,4 '-dimethoxy diphenylamines of equimolar amounts, and other steps are same as Example 1, you can are changed Close object HT87.Mass spectrum m/z：662.35 (calculated values：660.78).Theoretical elemental content (%) C45H32N4O2：C,81.80；H, 4.88；N,8.48；O,4.84.Survey constituent content (%)：C,81.77；H,4.86；N,8.45；O,4.87.The above results confirm Acquisition product is target product.
Embodiment 8：The preparation of compound HT95
The preparation of compound M-4：The 2- amino anthracenes of equimolar amounts are replaced with by aniline -2,3,4,5,6-d5,2- is bromo- 9,9 '-spiral shell, two fluorenes is replaced with the 3- bromodiphenylthiophenes of equimolar amounts, other steps with compound M-1 in embodiment 2 It prepares identical, you can obtain compound M-4.
The preparation of compound N -4：The bromo- 6- methyl -8- amino of 3- that the bromo- 8- aminoquinolines of 3- are replaced with equimolar amounts Quinoline, other steps in embodiment 3 intermediate N 1 prepare it is identical, you can obtain intermediate N 4.
The preparation of intermediate B -6：Compound N -1 is replaced with to the compound N -4 of equimolar amounts, by 3- methylphenylboronic acids Pinacol ester is replaced with the 4- yl-quinoline pinacol borates of equimolar amounts, other steps with intermediate B-in embodiment 3 1 preparation method is identical, you can obtains intermediate B -6.
The preparation of intermediate C-4：Intermediate B -2 is replaced with to the intermediate B -6 of equimolar amounts, other steps with reality The preparation method for applying intermediate C-1 in example 4 is identical, you can obtains intermediate C-4.
The preparation of intermediate D-4：Intermediate C-1 is replaced with to the intermediate C-4 of equimolar amounts, by bromo- 1, the 3- of 2- bis- The bromo- 3- iodobenzenes of 1- that fluoro- 5- iodobenzenes are replaced with equimolar amounts, preparation side of other steps with intermediate D-1 in embodiment 4 Method is identical, you can obtains intermediate D-4.
The preparation of compound HT95：3- bromine phenanthrolines are substituted for the intermediate D-4 of equimolar amounts, by two (4- biphenyl Base) amine is replaced with the compound M-4 of equimolar amounts, and other steps are same as Example 1, you can obtain compound HT95. Mass spectrum m/z：768.94 (calculated values：770.95).Theoretical elemental content (%) C54H34N4S：C,84.13；H,4.45；N,7.27； S,4.16.Survey constituent content (%)：C,84.10；H,4.42；N,7.29；S,4.20.The above results confirm that it is mesh to obtain product Mark product.
Embodiment 9：The preparation of red organic electroluminescence device 1
First, it is formed with the thickness vacuum deposition 2-TNATA of 60nm in the ITO layer (anode) for being formed in organic substrate Hole injection layer；Hole transmission layer is formed with the thickness vacuum evaporation NPB of 60nm on above-mentioned hole injection layer；Later, exist Using the thickness vacuum evaporation compound HT5 of 20nm as luminous auxiliary layer on hole transmission layer；Then, in above-mentioned luminous auxiliary layer On with weight ratio be 95:5 CBP and (piq)2Ir (acac) vacuum depositions are as luminescent layer, thickness 30nm；Then, upper It states and hole blocking layer is formed with the thickness vacuum deposition BAlq of 10nm on luminescent layer；With 40nm's on above-mentioned hole blocking layer Thickness vacuum deposition Alq3To form electron transfer layer；Then, LiF is deposited as electron injecting layer using the thickness of 0.2nm；Most Afterwards, cathode is formed with the thickness depositing Al of 150nm.
Embodiment:10：The preparation of red organic electroluminescence device 2
Compound HT5 is replaced with compound HT12, other steps are same as Example 9.
Embodiment 11：The preparation of red organic electroluminescence device 3
Compound HT5 is replaced with compound HT26, other steps are same as Example 9.
Embodiment 12：The preparation of red organic electroluminescence device 4
Compound HT5 is replaced with compound HT39, other steps are same as Example 9.
Embodiment 13：The preparation of red organic electroluminescence device 5
Compound HT5 is replaced with compound HT59, other steps are same as Example 9.
Embodiment 14：The preparation of red organic electroluminescence device 6
Compound HT5 is replaced with compound HT72, other steps are same as Example 9.
Embodiment 15：The preparation of red organic electroluminescence device 7
Compound HT5 is replaced with compound HT75, other steps are same as Example 9.
Embodiment 16：The preparation of red organic electroluminescence device 8
Compound HT5 is replaced with compound HT87, other steps are same as Example 9.
Embodiment 17：The preparation of red organic electroluminescence device 9
Compound HT5 is replaced with compound HT90, other steps are same as Example 9.
Embodiment 18：The preparation of red organic electroluminescence device 10
Compound HT5 is replaced with compound HT104, other steps are same as Example 9.
Embodiment 19：The preparation of red organic electroluminescence device 11
First, it is formed with the thickness vacuum deposition 2-TNATA of 60nm in the ITO layer (anode) for being formed in organic substrate Hole injection layer；Hole transmission layer is formed with the thickness vacuum evaporation compound HT5 of 60nm on above-mentioned hole injection layer；It Afterwards, on the hole transport layer using the thickness vacuum evaporation compound HT75 of 20nm as luminous auxiliary layer；Then, it shines above-mentioned With weight ratio for 95 on auxiliary layer:5 CBP and (piq)2Ir (acac) vacuum depositions are as luminescent layer, thickness 30nm；It connects It, hole blocking layer is formed with the thickness vacuum deposition BAlq of 10nm on above-mentioned luminescent layer；On above-mentioned hole blocking layer With the thickness vacuum deposition Alq of 40nm3To form electron transfer layer；Then, LiF is deposited using the thickness of 0.2nm to note as electronics Enter layer；Finally, cathode is formed with the thickness depositing Al of 150nm.
Embodiment 20：The preparation of red organic electroluminescence device 12
HT5 is replaced with compound HT12, other steps are identical as embodiment 19.
Embodiment 21：The preparation of red organic electroluminescence device 13
HT5 is replaced with compound HT26, other steps are identical as embodiment 19.
Embodiment 22：The preparation of red organic electroluminescence device 14
HT5 is replaced with compound HT39, other steps are identical as embodiment 19.
Embodiment 23：The preparation of red organic electroluminescence device 15
HT5 is replaced with compound HT59, other steps are identical as embodiment 19.
Embodiment 24：The preparation of red organic electroluminescence device 16
HT5 is replaced with compound HT72, other steps are identical as embodiment 19.
Embodiment 25：The preparation of red organic electroluminescence device 17
HT5 is replaced with compound HT75, other steps are identical as embodiment 19.
Embodiment 26：The preparation of red organic electroluminescence device 18
HT5 is replaced with compound HT87, other steps are identical as embodiment 19.
Embodiment 27：The preparation of red organic electroluminescence device 19
HT5 is replaced with compound HT90, other steps are identical as embodiment 19.
Embodiment 28：The preparation of red organic electroluminescence device 20
HT5 is replaced with compound HT104, other steps are identical as embodiment 19.
Comparative example：The preparation of red organic electroluminescence device 21
Other than not forming luminous auxiliary layer this point, luminescent device has been made in method same as Example 9.
Compound involved in the embodiment of the present invention and comparative example is as follows：
The luminescent properties for the organic electroluminescence device that the embodiment of the present invention is prepared are as shown in the table：
The above result shows that the aryl amine derivatives provided by the invention containing phenanthroline, have high hole mobility, And compound is stablized, and film forming also there is the highest between hole transmission layer and luminescent layer to have occupied molecule rail Road energy level, and there is high T1 values and refractive index, it is applied to organic electroluminescence device as luminous auxiliary layer and hole transmission layer In, it can realize the equalizing charge in luminescent layer, moreover it is possible to improve the luminous efficiency, heat resistance and service life of OLED device, together When reduce device driving voltage, be the luminous organic material of a kind of function admirable.
Obviously, the explanation of above example is only intended to facilitate the understanding of the method and its core concept of the invention.It should refer to Go out, it, without departing from the principle of the present invention, can also be to this hair for the those of ordinary skill of the technical field Bright some improvement and modification can also be carried out, these improvement and modification are also fallen within the protection scope of the claims of the present invention.

Claims (9)

1. a kind of aryl amine derivatives containing phenanthroline, which is characterized in that have the structure as shown in logical formula (I)：
Wherein, R1、R2、R3、R4、R5Independently selected from hydrogen, halogen, the substituted or unsubstituted alkyl of C1~C12, C6~C30 substitutions Or the substituted or unsubstituted heteroaryl of unsubstituted aryl, C3~C30；L is selected from singly-bound, C6~C30 substituted or unsubstituted two The substituted or unsubstituted divalent heteroaryl radical of valence aryl, C3~C30；Ar1、Ar2It is substituted or unsubstituted independently selected from C6~C60 The substituted or unsubstituted heteroaryl of aryl, C3~C60 or Ar1With Ar2It is interconnected to nitrogenous five-ring heterocycles.
2. the aryl amine derivatives according to claim 1 containing phenanthroline, which is characterized in that described contains adjacent luxuriant and rich with fragrance hello The aryl amine derivatives of quinoline have structure shown in logical formula (II) or (III)：
Wherein, R1、R2、R3、R4、R5Independently selected from hydrogen, fluorine atom, the substituted or unsubstituted alkyl of C1~C4, C6~C30 substitutions Or the substituted or unsubstituted heteroaryl of unsubstituted aryl, C3~C30；L is selected from singly-bound, C6~C30 substituted or unsubstituted two The substituted or unsubstituted divalent heteroaryl radical of valence aryl, C3~C30；Z1、Z2、Z3、Z4、Z5、Z6、Z7、Z8、Z9、Z10Independently selected from The substituted or unsubstituted alkyl of hydrogen, deuterium, cyano, halogen, C1~C4, the substituted or unsubstituted alkoxies of C1~C4, C6~C30 take Generation or the substituted or unsubstituted heteroaryl of unsubstituted aryl, C3~C60 or Z1、Z2、Z3、Z4、Z5、Z6、Z7、Z8、Z9、Z10In Two substituent groups of arbitrary neighborhood are connected to form ring.
3. the aryl amine derivatives according to claim 1 containing phenanthroline, which is characterized in that the L be selected from singly-bound or The following group of person：
Wherein, Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8Independently selected from hydrogen, deuterium, cyano, fluorine atom, methyl, ethyl, n-propyl, different Propyl, normal-butyl, sec-butyl, isobutyl group, tertiary butyl.
4. the aryl amine derivatives according to claim 1 containing phenanthroline, which is characterized in that described contains adjacent luxuriant and rich with fragrance hello The aryl amine derivatives of quinoline have structure shown in following general formula：
Wherein, R1、R2、R3、R4、R5Independently selected from hydrogen, fluorine atom, the substituted or unsubstituted alkyl of C1~C4, C6~C30 substitutions Or the substituted or unsubstituted heteroaryl of unsubstituted aryl, C3~C30；Z1、Z2、Z3、Z4、Z5、Z6、Z7、Z8、Z9、Z10Independently select From hydrogen, deuterium, cyano, halogen, the substituted or unsubstituted alkyl of C1~C4, the substituted or unsubstituted alkoxies of C1~C4, C6~C30 The substituted or unsubstituted heteroaryl of substituted or unsubstituted aryl, C3~C60 or Z1、Z2、Z3、Z4、Z5、Z6、Z7、Z8、Z9、Z10 Two substituent groups of middle arbitrary neighborhood are connected to form ring；Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8Independently selected from hydrogen, deuterium, cyano, fluorine Atom, methyl, ethyl, n-propyl, isopropyl, normal-butyl, sec-butyl, isobutyl group, tertiary butyl.
5. the aryl amine derivatives according to claim 1 containing phenanthroline, which is characterized in that the R1、R2、R3、R4、 R5Independently selected from hydrogen, fluorine atom, methyl or following group：
Wherein, X1、X2、X3、X4、X5、X6、X7、X8、X9Independently selected from hydrogen, deuterium, fluorine atom, cyano, methyl, ethyl, n-propyl, Isopropyl, normal-butyl, isobutyl group, tertiary butyl, sec-butyl, methoxyl group, difluoromethyl, trifluoromethyl.
6. the aryl amine derivatives according to claim 1 containing phenanthroline, which is characterized in that described contains adjacent luxuriant and rich with fragrance hello Any one of the aryl amine derivatives of quinoline in HT1~HT104 as follows：
7. a kind of organic electroluminescence device, which is characterized in that including cathode, anode and be placed in the cathode and the anode it Between one or more organic matter layers；Containing according to any one of claims 1 to 6 containing adjacent luxuriant and rich with fragrance in the organic matter layer The aryl amine derivatives of hello quinoline.
8. organic electroluminescence device according to claim 7, which is characterized in that containing luminous in the organic matter layer Auxiliary layer；Containing according to any one of claims 1 to 6, the arylamine containing phenanthroline derives in the luminous auxiliary layer Object.
9. organic electroluminescence device according to claim 7, which is characterized in that contain hole in the organic matter layer Transport layer；Containing according to any one of claims 1 to 6, the arylamine containing phenanthroline derives in the hole transmission layer Object.
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CN108558873A (en) * 2018-05-18 2018-09-21 长春海谱润斯科技有限公司 A kind of aromatic amine derivant and its organic electroluminescence device
CN108658980A (en) * 2018-05-18 2018-10-16 长春海谱润斯科技有限公司 A kind of aromatic amine compounds and its organic electroluminescence device containing phenanthroline
WO2021012407A1 (en) * 2019-07-23 2021-01-28 武汉华星光电半导体显示技术有限公司 Optical coupling output material and preparation method therefor, and electroluminescent device
US20210340137A1 (en) * 2019-07-23 2021-11-04 Wuhan China Star Optoelectronics Semiconductor Display Technology Co., Ltd. Light out-coupling material, manufacturing method thereof, and electroluminescent device
US20210408395A1 (en) * 2019-09-11 2021-12-30 Lg Display Co., Ltd. Organic compound and organic light emitting diode and organic light emitting display device including the same
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