CN109467511A - A kind of aromatic amine compounds and its organic luminescent device - Google Patents

A kind of aromatic amine compounds and its organic luminescent device Download PDF

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CN109467511A
CN109467511A CN201811343648.3A CN201811343648A CN109467511A CN 109467511 A CN109467511 A CN 109467511A CN 201811343648 A CN201811343648 A CN 201811343648A CN 109467511 A CN109467511 A CN 109467511A
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aromatic amine
amine compounds
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substituted
group
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韩春雪
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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    • H10K85/631Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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    • C07C211/57Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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    • H10K50/10OLEDs or polymer light-emitting diodes [PLED]
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    • H10K85/615Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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    • H10K85/657Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H10K85/6574Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • C07C2603/06Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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Abstract

The invention discloses a kind of aromatic amine compounds and its organic luminescent devices, are related to organic optoelectronic materials technology.Such compound is by connecting triphenylene group and substituted or unsubstituted benzo fluorene group in arylamine human subject structure, to obtain new compound, the aromatic amine compounds which forms have good cavity transmission ability.Preparation method is simple, raw material is easy to get, and has good thermal stability and chemical stability, while having good cavity transmission ability.Such compound is applied in OLED device as hole transmission layer, the luminous efficiency of device can be improved significantly, the driving voltage of device can also be effectively reduced simultaneously, solve the problems, such as that luminous efficiency of the existing technology is low, driving voltage is high, be the OLED material of a kind of function admirable.

Description

A kind of aromatic amine compounds and its organic luminescent device
Technical field
The present invention relates to organic photoelectrical material technical field more particularly to a kind of aromatic amine compounds and its organic illuminator Part.
Background technique
The Tang etc. of Kodak Company in 1987 has invented sandwich type organic bilayer film luminescent device, this is breakthrough Progress allows it is seen that the great potential that OLED technology move towards functionization, moves towards commercial market, has started organic light-emitting diodes The research boom of pipe.Over 30 years, OLED technology achieves development with rapid changepl. never-ending changes and improvements, moves towards the industrialization life from laboratory research It produces.
Currently, the development of OLED material is to the stage of a comparative maturity, Materials Co., Ltd both domestic and external is provided Hundreds of innovative material is provided with selecting.Oled light sulfate ferroelectric functional material applied to OLED device can be divided into two from purposes Major class, i.e. charge inject transmission material and luminescent material, further, can also inject charge into transmission material and be divided into electron injection biography Transmission material is injected in defeated material and hole, and luminescent material can also be divided into main body luminescent material and dopant material.In order to make High performance OLED luminescent device, it is desirable that various organic functional materials have good photoelectric characteristic, for example, are used for organic electroluminescence The hole mobile material of luminescence studies, hole mobile material are organic semi-conductor important components, and in general, hole passes Defeated material should meet following condition: (1) good film forming and thermal stability;(2) relatively small electron affinity energy, has Conducive to blocking electron injection;(3) relatively low ionization energy is conducive to hole injection;(4) preferable electrochemical stability;(5) High hole mobility is conducive to hole transport;(6) there is the level structure to match with luminescent layer.
All in all, the direction of the following OLED be develop high efficiency, high brightness, the long-life, low cost white light parts and Full color display device, but the technological industrialization process still faces many critical issues, wherein and electron-transport speed is higher than sky Cave transmission speed, caused by carrier injection and transmission imbalance be limitation organic luminescent device luminous efficiency and driving voltage drop Low key factor, how to develop a kind of good organic photoelectrical material of hole transport performance becomes urgent problem to be solved.
Summary of the invention
It is provided by the invention to organise the object of the present invention is to provide a kind of aromatic amine compounds and its organic luminescent device Closing object has good cavity transmission ability, and thermal stability is good, and good film-forming property, synthetic method is simple to operation, uses the arylamine There is the organic luminescent device of class compound preparation good luminous efficiency and service life to show.
The present invention provides a kind of aromatic amine compounds, and general formula of molecular structure is as shown in chemical formula I:
Wherein, A is selected from one of C6~C25 aryl, C3~C18 heteroaryl;
Ar1Selected from one of substituted or unsubstituted C6~C25 aryl, substituted or unsubstituted C3~C18 heteroaryl;
R1、R2Independently selected from substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C25 aryl, take One of generation or unsubstituted C3~C18 heteroaryl.
Preferably, general formula of molecular structure is as shown in chemical formula II:
Wherein, any one of A in group shown in 1a to 1d:
" * " is group link position;
R1、R2Independently selected from C1~C4 alkyl, phenyl, naphthalene, anthryl, phenanthryl, pyrenyl, fluorenyl, carbazyl, pyridyl group, Pyrimidine radicals, phenothiazinyl, phenoxazine base, acridinyl, dibenzothiophene, dibenzofuran group, benzothienyl, benzofuran One of base;
Ar1Any one in shown group:
Wherein, R3、R4、R5、R6、R7Independently selected from H, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthalene, anthryl, Phenanthryl, pyrenyl, fluorenyl, two fluorenyl of spiral shell, carbazyl, pyridyl group, phenothiazinyl, phenoxazine base, acridinyl, dibenzothiophene, Dibenzofuran group, benzothienyl, any one in benzofuranyl;
R8、R9Independently selected from methyl, ethyl, isopropyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted Naphthalene in any one, wherein substituent group is methyl, ethyl, isopropyl, tert-butyl, phenyl, any one in naphthalene Or it is a variety of.
Preferably, Ar1Any one in shown group:
Preferably, R1、R2Independently selected from any in methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthalene, xenyl It is a kind of.
Most preferably, any one of aromatic amine compounds of the invention in chemical structure as follows:
The present invention also provides a kind of organic luminescent device, the organic luminescent device includes cathode, anode and is placed in institute State between two electrodes and except one or more organic matter layers, the organic matter layer contains any virtue of the present invention Aminated compounds.
Preferably, organic matter layer of the present invention includes hole transmission layer, is contained in hole transmission layer of the present invention Any aromatic amine compounds.
Beneficial effects of the present invention:
The present invention provides a kind of aromatic amine compounds and its organic luminescent device.The present invention passes through in arylamine human subject structure On, triphenylene group and substituted or unsubstituted benzo fluorene group are connected, to obtain new compound.On the one hand, the combination The aromatic amine compounds that mode is formed have good cavity transmission ability, are applied to be used as hole transport in organic luminescent device Layer can effectively improve the transmittability in hole, improve hole and electronics in the recombination rate of luminescent layer, improve the luminous effect of device Rate.
On the other hand, since triphenylene group, benzo fluorene group have special rigid plane condensed cyclic structure, base can be made The whole movement of group is relatively limited, therefore can effectively improve glass transition temperature (Tg), and thermal stability is good.
Aromatic amine compounds preparation method of the present invention is simple, and raw material is easy to get, and can satisfy industrialization demand.
Aromatic amine compounds of the present invention are applied in organic luminescent device, can be used as hole transmission layer, using this The organic luminescent device for inventing the aromatic amine compounds preparation has good luminous efficiency and reduces the driving voltage of device.
Specific embodiment:
It is clearly and completely described below in conjunction with the technical solution of the embodiment of the present invention, it is clear that described implementation Example is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, art technology Personnel's every other embodiment obtained without making creative work, belongs to protection scope of the present invention.
Alkyl of the present invention refers to alkyl made of minusing a hydrogen atom in alkane molecule, can be straight chain alkane Base, branched alkyl, naphthenic base, example may include methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, tertiary fourth Base, amyl, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Aryl of the present invention refers to remove a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule after, be left the total of univalent perssad Claiming, can be monocyclic aryl or fused ring aryl, example may include phenyl, xenyl, naphthalene, anthryl, phenanthryl or pyrenyl etc., but It is without being limited thereto.
Heteroaryl of the present invention refers to the group that one or more aromatic core carbon in aryl are substituted by hetero atom General name, the hetero atom include but is not limited to oxygen, sulphur or nitrogen-atoms, and the heteroaryl can be bicyclic heteroaryl or condensed ring heteroaryl Base, example may include pyridyl group, pyrrole radicals, thienyl, furyl, benzothienyl, benzofuranyl, dibenzofuran group, Dibenzothiophene, carbazyl etc., but not limited to this.
Substituted alkyl of the present invention, substituted aryl, substituted heteroaryl, the substituent group is independently selected from first Base, ethyl, isopropyl, tert-butyl, phenyl, naphthalene, anthryl, phenanthryl, benzo phenanthryl, base, pyrenyl, benzyl, fluorenyl, 9,9- Dimethyl fluorenyl, hexichol amido, dimethylamino, carbazyl, 9- phenyl carbazole base, furyl, thienyl, deuterium base, phenothiazinyl, Phenoxazine base, acridinyl, xenyl, terphenyl etc., but not limited to this.
The present invention provides a kind of aromatic amine compounds, and general formula of molecular structure is as shown in chemical formula I:
Wherein, A is selected from one of C6~C25 aryl, C3~C18 heteroaryl;
Ar1Selected from one of substituted or unsubstituted C6~C25 aryl, substituted or unsubstituted C3~C18 heteroaryl;
R1、R2Independently selected from substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C25 aryl, take One of generation or unsubstituted C3~C18 heteroaryl.
Preferably, general formula of molecular structure is as shown in chemical formula II:
Wherein, any one of A in group shown in 1a to 1d:
" * " is group link position;
R1、R2Independently selected from C1~C4 alkyl, phenyl, naphthalene, anthryl, phenanthryl, pyrenyl, fluorenyl, carbazyl, pyridyl group, Pyrimidine radicals, phenothiazinyl, phenoxazine base, acridinyl, dibenzothiophene, dibenzofuran group, benzothienyl, benzofuran One of base;
Ar1Any one in shown group:
Wherein, R3、R4、R5、R6、R7Independently selected from H, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthalene, anthryl, Phenanthryl, pyrenyl, fluorenyl, two fluorenyl of spiral shell, carbazyl, pyridyl group, phenothiazinyl, phenoxazine base, acridinyl, dibenzothiophene, Dibenzofuran group, benzothienyl, any one in benzofuranyl;
R8、R9Independently selected from methyl, ethyl, isopropyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted Naphthalene in any one, wherein substituent group is methyl, ethyl, isopropyl, tert-butyl, phenyl, any one in naphthalene Or it is a variety of.
Preferably, Ar1Any one in shown group:
Preferably, R1、R2Independently selected from any in methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthalene, xenyl It is a kind of.
Most preferably, as an example, it is not particularly limited, a kind of aromatic amine compounds of the present invention are selected from as follows Any one in chemical structure:
It is enumerated above some specific constructive forms of aromatic amine compounds of the present invention, but the invention is not limited to These listed chemical structures, all based on structure shown in formula I, Ar1、R1、R2It should be all included in for group as defined above It is interior.
The preparation method of aromatic amine compounds of the present invention can be prepared by conventional coupling reaction, such as can It is prepared by following synthetic route, however, the present invention is not limited thereto:
Aromatic amine compounds A occurs Buchwald with bromide B first and reacts, and obtains intermediate M;Intermediate M again with contain There is Ar1Bromide C occur Buchwald reaction, finally obtain target compound I.
Wherein, A is selected from one of C6~C25 aryl, C3~C18 heteroaryl;
Ar1Selected from one of substituted or unsubstituted C6~C25 aryl, substituted or unsubstituted C3~C18 heteroaryl;
R1、R2Independently selected from substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C25 aryl, take One of generation or unsubstituted C3~C18 heteroaryl.
The present invention does not have special limitation to the above-mentioned reaction condition respectively reacted, and use is well-known to those skilled in the art Reaction condition.The present invention is not particularly limited the source of raw material employed in above-mentioned each reaction, can be commercially available Product is prepared using preparation method well-known to those skilled in the art.Aromatic amine compounds synthesis step of the present invention Suddenly less, processing it is simple, easy to industrialized production.
The present invention also provides a kind of organic luminescent device, the organic luminescent device includes cathode, anode and is placed in institute State between two electrodes and except one or more organic matter layers, the organic matter layer contains arylamine class of the present invention Close object.
Preferably, the organic matter layer includes hole transmission layer, is contained in hole transmission layer of the present invention any Aromatic amine compounds.
OLED structure of the present invention are as follows: ITO is as transparent anode;2-TNATA is used as hole injection layer; Aromatic amine compounds of the present invention are as hole transmission layer;CBP:Ir (ppy)3As luminescent layer substance;TPBi is used as electricity Sub- transport layer;LiF is used as electron injecting layer;Al is used as cathode.
Its structure of aromatic amino-derivative and its organic luminescent device of the present invention is preferred are as follows: substrate/anode/hole note Enter layer/hole transmission layer/luminescent layer/electron transfer layer/electron injecting layer/cathode.However, the structure of organic luminescent device is unlimited In this.Aromatic amino-derivative and its organic luminescent device of the present invention can according to the characteristic of device parameter requirements and material into Row selection and combination, can also add or omit part organic layer.OLED structure of the present invention are as follows: ITO conduct Transparent anode;2-TNATA is used as hole injection layer;NPB or aromatic amino-derivative of the present invention are used as hole transmission layer; CBP:Ir (ppy)3As luminescent layer;TPBi is used as electron transfer layer;LiF is used as electron injecting layer;Al is used as cathode.
Aromatic amine compounds of the present invention are used as hole mobile material, to manufacture the organic of construction same as below Luminescent device:
ITO/2-TNATA (50nm)/aromatic amine compounds of the present invention (30nm)/CBP:Ir (ppy)3(30nm)/ TPBi(30nm)/LiF(0.5nm)/Al(200nm)。
The preparation of organic matter layer can be vacuum vapour deposition, spin-coating method, vapor deposition, knife coating, laser thermal transfer, EFI Rubbing method, slit coating method, any one in dipping formula rubbing method, preferably use the side of vacuum evaporation in the present invention Method.
Organic luminescent device of the present invention can be widely applied to Display panel, lighting source, flexibility OLED, Electronic Paper, The fields such as Organophotoreceptor or Organic Thin Film Transistors, direction board, signal lamp.
The synthesis of [embodiment 1] compound 1
Step1: under argon atmospher, by amine compounds A-1 (3.65g, 15mmol), bromide B-1 (5.01g, 15mmol), uncle Sodium butoxide (2.88g, 30mmol) is added in 150ml dehydrated toluene, stirs lower addition palladium acetate (0.07g, 0.3mmol), three Tert-butyl phosphine (0.06g, 0.3mmol) reacts 8 hours at 80 DEG C.It after cooling, is filtered, is filtered by diatomite/silica gel funnel For liquid by vacuum distillation removal organic solvent, residue obtained to recrystallize in toluene, leaching obtained solid is dry, obtains centre Body M-1.
Step2: under argon atmospher, to intermediate M-1 (4.36g, 10mmol), bromide C-1 (2.45g, 10mmol), three (dibenzalacetone) two palladium (0.14g, 0.15mmol), tri-tert-butylphosphine tetrafluoroborate (0.087g, 0.3mmol), tertiary fourth 50ml anhydrous dimethyl benzene is added in sodium alkoxide (1.9g, 20mmol), is flowed back 8 hours.50 DEG C are cooled to, diatomite/silica gel mistake is passed through Filter, filtrate concentration, residue obtained to be purified with silica gel column chromatography, gained crude product recrystallizes in toluene, obtains compound 1 (4.21g, 66%), yield.
Mass spectrum m/z:637.30 (calculated value: 637.28).Theoretical elemental content (%) C49H35N:C, 92.27;H,5.53; N,2.20.Survey constituent content (%): C, 92.26;H,5.54;N,2.20.The above results confirm that obtaining product is target product.
The synthesis of [embodiment 2] compound 2
Bromide C-1 is replaced with to the bromide C-2 of equimolar amounts, other steps are same as Example 1, can obtain To compound 2 (4.33g, 68%).
Mass spectrum m/z:637.29 (calculated value: 637.28).Theoretical elemental content (%) C49H35N:C, 92.27;H, 5.53; N, 2.20 actual measurement constituent content (%): C, 92.28;H, 5.52;N, 2.20.The above results confirm that obtaining product is target product.
The synthesis of [embodiment 3] compound 13
Bromide C-1 is replaced with to the bromide C-13 of equimolar amounts, obtains chemical combination according to the synthetic method of compound 1 Object 13 (4.36g, 67%).
Mass spectrum m/z:651.25 (calculated value: 651.26).Theoretical elemental content (%) C49H33NO:C, 90.29;H, 5.10; N, 2.15;O, 2.45 actual measurement constituent content (%): C, 90.29;H, 5.11;N, 2.15;O, 2.44.The above results confirmation is produced Object is target product.
The synthesis of [embodiment 4] compound 17
Bromide C-1 is replaced with to the bromide C-17 of equimolar amounts, obtains chemical combination according to the synthetic method of compound 1 Object 17 (4.21g, 63%).
Mass spectrum m/z:801.35 (calculated value: 801.34).Theoretical elemental content (%) C49H33NS:C, 88.12;H, 4.98; N, 2.10;S, 4.80 actual measurement constituent content (%): C, 88.13;H, 4.97;N, 2.10;S, 4.80.The above results confirmation is produced Object is target product.
The synthesis of [embodiment 5] compound 22
Bromide C-1 is replaced with to the bromide C-22 of equimolar amounts, obtains chemical combination according to the synthetic method of compound 1 Object 22 (4.58g, 63%).
Mass spectrum m/z:726.31 (calculated value: 726.30).Theoretical elemental content (%) C55H38N2: C, 90.88;H, 5.27; N, 3.85 actual measurement constituent content (%): C, 90.87;H, 5.28;N, 3.85.The above results confirm that obtaining product is target product.
The synthesis of [embodiment 6] compound 42
Bromide B-1 is replaced with to the bromide B-2 of equimolar amounts, bromide C-1 is replaced with the bromine of equimolar amounts Compound C-2, other steps are same as Example 1, and compound 42 (4.15g, 65%) can be obtained.
Mass spectrum m/z:637.82 (calculated value: 637.83).Theoretical elemental content (%) C49H35N:C, 92.27;H, 5.53; N, 2.20 actual measurement constituent content (%): C, 92.26;H, 5.54;N, 2.20.The above results confirm that obtaining product is target product.
The synthesis of [embodiment 7] compound 58
Bromide B-1 is replaced with to the bromide B-2 of equimolar amounts, bromide C-1 is replaced with the bromine of equimolar amounts Compound C-58, other steps are same as Example 1, and compound 58 (3.09g, 69%) can be obtained.
Mass spectrum m/z:677.32 (calculated value: 677.31).Theoretical elemental content (%) C52H39N:C, 92.13;H, 5.80; N, 2.07 actual measurement constituent content (%): C, 92.14;H, 5.80;N, 2.06.The above results confirm that obtaining product is target product.
The synthesis of [embodiment 8] compound 82
Bromide B-1 is replaced with to the bromide B-3 of equimolar amounts, bromide C-1 is replaced with the bromine of equimolar amounts Compound C-2 obtains compound 82 (3.89g, 61%) according to the synthetic method of compound 1.
Mass spectrum m/z:637.82 (calculated value: 637.83).Theoretical elemental content (%) C49H35N:C, 92.27;H, 5.53; N, 2.20 actual measurement constituent content (%): C, 92.26;H, 5.54;N, 2.20.The above results confirm that obtaining product is target product.
The synthesis of [embodiment 9] compound 93
Bromide B-1 is replaced with to the bromide B-3 of equimolar amounts, bromide C-1 is replaced with the bromine of equimolar amounts Compound C-13 obtains compound 93 (4.04g, 62%) according to the synthetic method of compound 1.
Mass spectrum m/z:651.25 (calculated value: 651.26).Theoretical elemental content (%) C49H33NO:C, 90.29;H, 5.10; N, 2.15;O, 2.45 actual measurement constituent content (%): C, 90.29;H, 5.11;N, 2.15;O, 2.44.The above results confirmation is produced Object is target product.
The synthesis of [embodiment 10] compound 117
Bromide B-1 is replaced with to the bromide B-3 of equimolar amounts, bromide C-1 is replaced with the bromine of equimolar amounts Compound C-117 obtains compound 117 (3.48g, 70%) according to the synthetic method of compound 1.
Mass spectrum m/z:687.30 (calculated value: 687.29).Theoretical elemental content (%) C53H37N:C, 92.54;H, 5.42; N, 2.04 actual measurement constituent content (%): C, 92.55;H, 5.41;N, 2.04.The above results confirm that obtaining product is target product.
[comparative example 1] device prepares embodiment:
Ito glass substrate is placed in distilled water and is cleaned 2 times, it is ultrasonic washing 15 minutes, different after distilled water cleans Ultrasonic washing is later dry in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base Plate washs 5 minutes, is sent in evaporator.
Hole injection layer 2-TNATA/50nm is successively deposited on the ito transparent electrode having had been prepared for, vapor deposition hole passes Defeated layer NPB/30nm, vapor deposition main body CBP: doping Ir (ppy)35% mixing/30nm, then vapor deposition electron transfer layer TPBi/ 30nm, cathode LiF/0.5nm, Al/200nm.
[Application Example 1-10]
To compare the NPB in Application Example 1 change into shown compound 1 in Application Example 1-10,2,13,17,22, 42、58、82、93、117。
Table 1 is the compound of preparation of the embodiment of the present invention and the characteristics of luminescence test for comparing luminescent device prepared by substance As a result.
The characteristics of luminescence of [table 1] luminescent device is tested
The above result shows that aromatic amine compounds of the invention are applied in organic luminescent device, especially as hole Transport layer shows the low advantage of high-luminous-efficiency, driving voltage, is luminous organic material of good performance.
It should be pointed out that the present invention is particularly described with individual embodiments, but before not departing from the principle of the invention It puts, ordinary skill people can carry out the improvement on various forms or details to the present invention, these improvement also fall into this hair In bright protection scope.

Claims (7)

1. a kind of aromatic amine compounds, which is characterized in that general formula of molecular structure is as shown in chemical formula I:
Wherein, A is selected from one of C6~C25 aryl, C3~C18 heteroaryl;
Ar1Selected from one of substituted or unsubstituted C6~C25 aryl, substituted or unsubstituted C3~C18 heteroaryl;
R1、R2Independently selected from substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C25 aryl, replace or One of unsubstituted C3~C18 heteroaryl.
2. a kind of aromatic amine compounds according to claim 1, which is characterized in that general formula of molecular structure such as II institute of chemical formula Show:
Wherein, any one of A in group shown in 1a to 1d:
" * " is group link position;
R1、R2Independently selected from C1~C4 alkyl, phenyl, naphthalene, anthryl, phenanthryl, pyrenyl, fluorenyl, carbazyl, pyridyl group, pyrimidine Base, phenothiazinyl, phenoxazine base, acridinyl, dibenzothiophene, dibenzofuran group, benzothienyl, in benzofuranyl One kind;
Ar1Any one in shown group:
Wherein, R3、R4、R5、R6、R7Independently selected from H, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthalene, anthryl, phenanthryl, Pyrenyl, fluorenyl, two fluorenyl of spiral shell, carbazyl, pyridyl group, phenothiazinyl, phenoxazine base, acridinyl, dibenzothiophene, dibenzo Furyl, benzothienyl, any one in benzofuranyl;
R8、R9Independently selected from methyl, ethyl, isopropyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene Any one in base, wherein substituent group be methyl, ethyl, isopropyl, tert-butyl, phenyl, in naphthalene any one or it is more Kind.
3. a kind of aromatic amine compounds according to claim 1, which is characterized in that Ar1It is any one in shown group Kind:
4. a kind of aromatic amine compounds according to claim 1, which is characterized in that R1、R2Independently selected from methyl, ethyl, Isopropyl, tert-butyl, phenyl, naphthalene, any one in xenyl.
5. a kind of aromatic amine compounds according to claim 1, which is characterized in that in chemical structure as follows Any one:
6. a kind of organic luminescent device, which is characterized in that the organic luminescent device include cathode, anode and be placed in it is described two electricity Between pole and except one or more organic matter layers, the organic matter layer contains the described in any item virtues of Claims 1 to 5 Aminated compounds.
7. a kind of organic luminescent device according to claim 6, which is characterized in that the organic matter layer includes that hole passes Defeated layer contains the described in any item aromatic amine compounds of Claims 1 to 5 in hole transmission layer.
CN201811343648.3A 2018-11-13 2018-11-13 A kind of aromatic amine compounds and its organic luminescent device Withdrawn CN109467511A (en)

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Cited By (6)

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Publication number Priority date Publication date Assignee Title
CN111606853A (en) * 2020-06-30 2020-09-01 上海天马有机发光显示技术有限公司 Arylamine compound, organic light-emitting device and display device
CN112939787A (en) * 2019-12-10 2021-06-11 北京鼎材科技有限公司 Compound and application thereof
CN113816863A (en) * 2021-10-29 2021-12-21 长春海谱润斯科技股份有限公司 Triarylamine compound, preparation method thereof and organic light-emitting device
CN113912531A (en) * 2021-08-23 2022-01-11 上海和辉光电股份有限公司 Novel arylamine compound and application thereof
CN114478265A (en) * 2020-11-13 2022-05-13 江苏三月科技股份有限公司 Arylamine compound and application thereof in organic electroluminescent device
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112939787A (en) * 2019-12-10 2021-06-11 北京鼎材科技有限公司 Compound and application thereof
CN111606853A (en) * 2020-06-30 2020-09-01 上海天马有机发光显示技术有限公司 Arylamine compound, organic light-emitting device and display device
CN111606853B (en) * 2020-06-30 2022-01-11 武汉天马微电子有限公司 Arylamine compound, organic light-emitting device and display device
CN114478265A (en) * 2020-11-13 2022-05-13 江苏三月科技股份有限公司 Arylamine compound and application thereof in organic electroluminescent device
CN114685360A (en) * 2020-12-31 2022-07-01 阜阳欣奕华材料科技有限公司 Carbazole compound, organic electroluminescent device and display device
CN113912531A (en) * 2021-08-23 2022-01-11 上海和辉光电股份有限公司 Novel arylamine compound and application thereof
CN113816863A (en) * 2021-10-29 2021-12-21 长春海谱润斯科技股份有限公司 Triarylamine compound, preparation method thereof and organic light-emitting device
CN113816863B (en) * 2021-10-29 2024-05-07 长春海谱润斯科技股份有限公司 Triarylamine compound, preparation method thereof and organic light-emitting device

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