CN108752261A - A kind of benzidine compound and its organic luminescent device - Google Patents

A kind of benzidine compound and its organic luminescent device Download PDF

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CN108752261A
CN108752261A CN201810789208.4A CN201810789208A CN108752261A CN 108752261 A CN108752261 A CN 108752261A CN 201810789208 A CN201810789208 A CN 201810789208A CN 108752261 A CN108752261 A CN 108752261A
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韩春雪
周雯庭
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The invention discloses a kind of benzidine compound and its organic luminescent devices, are related to organic optoelectronic materials technology.For such compound by arylamine human subject structure, connecting substituted or unsubstituted luxuriant and rich with fragrance carbazyl, 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 to as hole transmission layer in OLED device, the luminous efficiency of device can be significantly increased, the driving voltage that device can also effectively be reduced simultaneously, solves the problems, such as that luminous efficiency of the existing technology is low, driving voltage is high, is the OLED material of a kind of function admirable.

Description

A kind of benzidine compound and its organic luminescent device
Technical field
The present invention relates to organic photoelectrical material technical field more particularly to a kind of benzidine compounds and its organic illuminator Part.
Background technology
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 Production.
Currently, the development of OLED material is to the stage of a comparative maturity, Materials Co., Ltd both domestic and external provides 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 devices, 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.
Invention content
It is provided by the invention to organise the object of the present invention is to provide a kind of benzidine compound and its organic luminescent device Closing object has good hole transport and electronic blocking performance, and thermal stability is good, and good film-forming property, synthetic method is simple to operation, Using organic luminescent device prepared by the benzidine compound there is good luminous efficiency and service life to show.
The present invention provides a kind of benzidine compounds, and general formula of molecular structure is as shown in chemical formula I：
Wherein, Ra、RbIndependently selected from hydrogen, substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C25 Aryl, Ra、RbThe two can connect cyclization；
Ar1、Ar2、Ar3、Ar4Any one in following group：
Any one of L in following group：
R1、R2、R3、R4、R5Independently selected from H, cyano, halogen atom, substituted or unsubstituted C1~C10 alkyl, substitution Or one kind in unsubstituted C6~C25 aryl, substituted or unsubstituted C3~C18 heteroaryls；R6、R7、R8、R9、R10, R it is independent Ground be selected from substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C25 aryl, substituted or unsubstituted C3~ One kind in C18 heteroaryls.
Preferably, any one of structure in formula II-IV：
Preferably, Ar1、Ar2、Ar3、Ar4Any one in following group：
Any one of L in following group：
R1、R2、R3、R4、R5Independently selected from H, cyano, halogen atom or substituted or unsubstituted following group：C1~C6 Alkyl, phenyl, naphthalene, anthryl, phenanthryl, pyrenyl, fluorenyl, two fluorenyl of spiral shell, carbazyl, pyridyl group, pyrimidine radicals, phenothiazinyl, pheno Oxazinyl, acridinyl, dibenzothiophene, dibenzofuran group, benzothienyl, benzofuranyl, quinolyl or isoquinolin One kind in base；
R6、R7, R is independently selected from substituted or unsubstituted following group：C1~C4 alkyl, phenyl, naphthalene, anthryl, phenanthrene Base, pyrenyl, fluorenyl, carbazyl, pyridyl group, pyrimidine radicals, phenothiazinyl, phenoxazine groups, acridinyl, dibenzothiophene, hexichol And one kind in furyl, benzothienyl, benzofuranyl.
Preferably, Ar1、Ar2、Ar3、Ar4In it is at least one be selected from group as follows：
Preferably, any one of R in methyl, ethyl, isopropyl, tertiary butyl, substituted or unsubstituted phenyl.
Further preferably, R1、R2、R3、R4、R5Independently selected from the following groups of H or substituted or unsubstituted：C1~C4 alkyl, benzene Base, naphthalene, anthryl, phenanthryl, pyrenyl, fluorenyl, two fluorenyl of spiral shell, carbazyl, pyridyl group, phenothiazinyl, phenoxazine groups, acridinyl, Any one in dibenzothiophene, dibenzofuran group, benzothienyl, benzofuranyl；R6、R7, R independently selected from Any one in C1~C4 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene.
Most preferably, any one of benzidine compound of the invention in chemical constitution 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 of the present invention any Aniline compound.
Preferably, organic matter layer of the present invention includes hole transmission layer, is contained in hole transmission layer of the present invention Any benzidine compound.
Beneficial effects of the present invention：
A kind of benzidine compound of present invention offer and its organic luminescent device.The present invention passes through in arylamine human subject structure On, substituted or unsubstituted luxuriant and rich with fragrance carbazyl is connected, and obtain new compound.On the one hand, the benzidine which forms Compound has good cavity transmission ability and electron-blocking capability, is applied to be used as hole transport in organic luminescent device Layer can effectively improve the transmission in hole and reduce loss of the electronics to anode, improve hole and electronics luminescent layer recombination rate, Improve the luminous efficiency of device.
On the one hand, which increases the conjugated system of compound, and luxuriant and rich with fragrance carbazole group is due to including to carry in structure The nitrogen-atoms of lone pair electrons and the planar conjugate rigid structure stablized so that it not only has excellent photo and thermal stability, can be into The chemical substitute reaction in a variety of sites of row, and there is outstanding hole-transfer performance and preferable fluorescent emission ability, it is one The outstanding electron rich modified group of class.
On the other hand, since luxuriant and rich with fragrance carbazole group has special rigid plane condensed cyclic structure, the fortune of group entirety can be made It is dynamic relatively limited, therefore can effectively improve glass transition temperature (Tg).
Benzidine compound preparation method of the present invention is simple, and raw material is easy to get, and disclosure satisfy that industrialization demand.
Benzidine compound of the present invention is applied in organic luminescent device, can be used as hole transmission layer, using this Inventing organic luminescent device prepared by the benzidine compound has good luminous efficiency and reduces the driving voltage of device.
Specific implementation mode：
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 The every other embodiment that personnel are 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 refer to aromatic hydrocarbon molecule aromatic core carbon on remove a hydrogen atom after, be left univalent perssad it is total 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 of aryl aromatic core carbon is substituted 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, example may include pyridyl group, pyrrole radicals, pyrimidine radicals, thienyl, furyl, indyl, quinolyl, isoquinolyl, benzo thiophene Pheno base, 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, tertiary butyl, phenyl, naphthalene, anthryl, phenanthryl, benzo phenanthryl, base, pyrenyl, benzyl, fluorenyl, 9,9- Dimethyl fluorenyl, hexichol amido, dimethylamino, carbazyl, 9- phenyl carbazoles base, furyl, thienyl, cyano, halogen atom, Deuterium base, trifluoromethyl, phenothiazinyl, phenoxazine groups, acridinyl, piperidyl, pyridyl group, pyrazinyl, triazine radical, pyrimidine radicals, connection Phenyl, terphenyl, nitro etc., but not limited to this.
The present invention provides a kind of benzidine compounds, and general formula of molecular structure is as shown in chemical formula I：
Wherein, Ra、RbIndependently selected from hydrogen, substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C25 Aryl, Ra、RbThe two can connect cyclization；
R of the present inventiona、RbThe two can connect cyclization, refer to Ra、RbFluorenes ring, carbazole are connected into the adjacent phenyl rings at place Ring, dibenzofurans ring, dibenzothiophenes ring etc., but not limited to this.
Ar1、Ar2、Ar3、Ar4Any one in following group：
Any one of L in following group:
R1、R2、R3、R4、R5Independently selected from H, cyano, halogen atom, substituted or unsubstituted C1~C10 alkyl, substitution Or one kind in unsubstituted C6~C25 aryl, substituted or unsubstituted C3~C18 heteroaryls；R6、R7、R8、R9、R10, R it is independent Ground be selected from substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C25 aryl, substituted or unsubstituted C3~ One kind in C18 heteroaryls.
Preferably, any one of structure in formula II-IV：
Preferably, Ar1、Ar2、Ar3、Ar4Any one in following group：
Any one of L in following group：
R1、R2、R3、R4、R5Independently selected from H, cyano, halogen atom or substituted or unsubstituted following group：C1~C6 Alkyl, phenyl, naphthalene, anthryl, phenanthryl, pyrenyl, fluorenyl, two fluorenyl of spiral shell, carbazyl, pyridyl group, pyrimidine radicals, phenothiazinyl, pheno Oxazinyl, acridinyl, dibenzothiophene, dibenzofuran group, benzothienyl, benzofuranyl, quinolyl or isoquinolin One kind in base；
R6、R7, R is independently selected from substituted or unsubstituted following group：C1~C4 alkyl, phenyl, naphthalene, anthryl, phenanthrene Base, pyrenyl, fluorenyl, carbazyl, pyridyl group, pyrimidine radicals, phenothiazinyl, phenoxazine groups, acridinyl, dibenzothiophene, hexichol And one kind in furyl, benzothienyl, benzofuranyl.
Preferably, Ar1、Ar2、Ar3、Ar4In it is at least one be selected from group as follows：
Preferably, any one of R in methyl, ethyl, isopropyl, tertiary butyl, substituted or unsubstituted phenyl.
Further preferably, R1、R2、R3、R4、R5Independently selected from the following groups of H or substituted or unsubstituted：C1~C4 alkyl, benzene Base, naphthalene, anthryl, phenanthryl, pyrenyl, fluorenyl, two fluorenyl of spiral shell, carbazyl, pyridyl group, phenothiazinyl, phenoxazine groups, acridinyl, Any one in dibenzothiophene, dibenzofuran group, benzothienyl, benzofuranyl；R6、R7, R independently selected from Any one in C1~C4 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene.
Most preferably, as an example, it is not particularly limited, a kind of benzidine compound of the present invention is selected from as follows Any one in chemical constitution：
The present invention obtains the biphenyl amination of chemical structure shown in formula I of the present invention by a series of Buchward coupling reactions Close object.
The present invention limitation not special to above-mentioned reaction be using popular response well-known to those skilled in the art Can, the preparation method is simple, easily operated.
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 biphenyl amination 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 Benzidine compound.
OLED structure of the present invention is：ITO is as transparent anode；2-TNATA is used as hole injection layer； Benzidine compound of the present invention is 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.
Benzidine compound of the present invention is used as hole mobile material, to manufacture the organic of construction same as below Luminescent device：
ITO/2-TNATA (50nm)/benzidine compound of the present invention (30nm)/CBP：Ir(ppy)3(30nm)/ TPBi(30nm)/LiF(0.5nm)/Al(200nm)。
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：In reactor be added benzidine-compound f (1.35g, 8mmol), compound g (1.55g, 6.67mmol)、Pd2(dba)3(0.17g, 0.2mmol), P (t-Bu)3(0.14,0.67mmol), NaOt-Bu (2.24g, 20mmol), toluene solution 100mL reacts for 24 hours under the conditions of 100 DEG C, and ether and water is used to extract organic phase after reaction, organic Layer MgSO4Dry, condensed organic crosses column chromatography, is recrystallized to give intermediate 1-b (1.61g, 75%).
Step2：It is sub- that compound a (1.53g, 8mmol), the N- bromines succinyl of (3.15g, 17.5mmol) are added in reactor The p-methyl benzenesulfonic acid of amine and (0.5g, 2.7mmol) are dissolved in the acetonitrile of 30ml respectively, stir about 12 hours under the conditions of 50 DEG C. It is cooled to room temperature, depressurizes, filter collects crystal, and then methanol washs to obtain compound b.Take compound b (1.80g, 6.67mmol) tied with methyl bromide c (0.76g, 8mmol), addition potassium tert-butoxide (2.83g, 25.2mmol), return stirring, reaction Shu Hou, is extracted with ethyl acetate vacuum distillation, dichloromethane and hexane and crosses pillar and obtain compound d (1.57g, 83%).
Step3：In reactor be added aniline-compound e (0.75g, 8mmol), compound d (1.90g, 6.67mmol), Pd2(dba)3(0.17g, 0.2mmol), P (t-Bu)3(0.14,0.67mmol), NaOt-Bu (2.24g, 20mmol), toluene are molten Liquid 100mL reacts for 24 hours under the conditions of 100 DEG C, ether and water is used to extract organic phase, organic layer MgSO after reaction4It is dry, Condensed organic crosses column chromatography, is recrystallized to give intermediate 1-a (1.44g, 73%).
Step4：Intermediate 1-a (2.49g, 8.4mmol), 4,4 '-two bromo- 1,1- biphenyl are added in reaction vessel (2.87g, 9.2mmol), potassium tert-butoxide (2.83g, 25.2mmol), Pd2(dba)3(0.07g, 0.08mmol), ultrasonic deoxygenation Three times, P (t-Bu) is added in dimethylbenzene 40mL, stirring and dissolving, displaced air3(0.07g, 0.34mmol), again displaced air three Secondary, back flow reaction 6h is cooled to room temperature, and enough dichloromethane is added, product is completely dissolved, and excessively a small amount of silica gel funnel removes Fall catalyst and salt, filtrate is concentrated into thick, crosses column chromatography, obtains compound 1-c (3.01g, 68%).
Step5：In reaction vessel be added intermediate 1-c (4.43g, 8.4mmol), intermediate 1-b (2.96g, 9.2mmol), potassium tert-butoxide (2.83g, 25.2mmol), Pd2(dba)3The dimethylbenzene of (0.07g, 0.08mmol), ultrasonic deoxygenation Three times, P (t-Bu) is added in 40mL, stirring and dissolving, displaced air3(0.07g, 0.34mmol), again displaced air three times, reflux 6h is reacted, is cooled to room temperature, enough dichloromethane is added, product is completely dissolved, excessively a small amount of silica gel funnel removes catalysis Agent and salt, filtrate be concentrated into it is thick, cross column chromatography, obtain compound 1 (4.19g, 65%).
Mass spectrum m/z：767.34 (calculated values：767.33).Theoretical elemental content (%) C57H41N3：C, 89.15；H, 5.38； N, 5.47 actual measurement constituent contents (%)：C, 89.15；H, 5.37；N, 5.48.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 2] compound 3
Compound 3 (3.86g, 62%) is obtained according to the synthetic method of compound 1.
Mass spectrum m/z：741.32 (calculated values：741.31).Theoretical elemental content (%) C55H39N3：C, 89.04；H, 5.30； N, 5.68 actual measurement constituent contents (%)：C, 89.05；H, 5.30；N, 5.67.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 3] compound 11
Compound 11 (4.28g, 63%) is obtained according to the synthetic method of compound 1.
Mass spectrum m/z：807.37 (calculated values：807.36).Theoretical elemental content (%) C60H45N3：C, 89.19；H, 5.61； N, 5.20 actual measurement constituent contents (%)：C, 89.20；H, 5.60；N, 5.20.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 4] compound 17
Compound 17 (4.26g, 62%) is obtained according to the synthetic method of compound 1.
Mass spectrum m/z：817.36 (calculated values：817.35).Theoretical elemental content (%) C61H43N3：C, 89.56；H, 5.30； N, 5.14 actual measurement constituent contents (%)：C, 89.57；H, 5.30；N, 5.13.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 5] compound 22
Compound 22 (4.53g, 61%) is obtained according to the synthetic method of compound 1.
Mass spectrum m/z：883.40 (calculated values：883.39).Theoretical elemental content (%) C66H49N3：C, 89.66；H, 5.59； N, 4.75 actual measurement constituent contents (%)：C, 89.67；H, 5.58；N, 4.75.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 6] compound 25
Compound 25 (4.67g, 60%) is obtained according to the synthetic method of compound 1.
Mass spectrum m/z：926.44 (calculated values：926.43).Theoretical elemental content (%) C68H54N4：C, 88.09；H, 5.87； N, 6.04 actual measurement constituent contents (%)：C, 88.09；H, 5.86；N, 6.05.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 7] compound 79
Compound 79 (4.63g, 59%) is obtained according to the synthetic method of compound 1.
Mass spectrum m/z：933.42 (calculated values：933.41).Theoretical elemental content (%) C70H51N3：C, 90.00；H, 5.50； N, 4.50 actual measurement constituent contents (%)：C, 90.00；H, 5.50；N, 4.50.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 8] compound 80
Compound 80 (4.79g, 61%) is obtained according to the synthetic method of compound 1.
Mass spectrum m/z：933.42 (calculated values：933.41).Theoretical elemental content (%) C70H51N3：C, 90.00；H, 5.50； N, 4.50 actual measurement constituent contents (%)：C, 90.00；H, 5.51；N, 4.49.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 9] compound 89
Compound 89 (4.40g, 62%) is obtained according to the synthetic method of compound 1.
Mass spectrum m/z：843.37 (calculated values：843.36).Theoretical elemental content (%) C63H45N3：C, 89.65；H, 5.37； N, 4.98 actual measurement constituent contents (%)：C, 89.66；H, 5.36；N, 4.98.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 10] compound 91
Compound 91 (4.33g, 63%) is obtained according to the synthetic method of compound 1.
Mass spectrum m/z：817.36 (calculated values：817.35).Theoretical elemental content (%) C61H43N3：C, 89.56；H, 5.30； N, 5.14 actual measurement constituent contents (%)：C, 89.57；H, 5.30；N, 5.13.The above results confirm that it is target product to obtain product.
The synthesis of [embodiment 11] compound 99
Compound 99 (4.21g, 62%) is obtained according to the synthetic method of compound 1.
Mass spectrum m/z：807.37 (calculated values：807.36).Theoretical elemental content (%) C60H45N3：C, 89.19；H, 5.61； N, 5.20 actual measurement constituent contents (%)：C, 89.19；H, 5.60；N, 5.21.The above results confirm that it is target product to obtain product.
[comparative example 1] device prepares embodiment：
Ito glass substrate is placed in distilled water and is cleaned 2 times, ultrasonic washing 15 minutes is 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 being already prepared to, vapor deposition hole passes Defeated layer NPB/30nm, vapor deposition main body CBP：Adulterate Ir (ppy)35% mixing/30nm and then vapor deposition electron transfer layer TPBi/ 30nm, cathode LiF/0.5nm, Al/200nm.
[Application Example 1-11]
By the NPB compared in Application Example 1 change into shown compound 1 in Application Example 1-11,3,11,17,22, 25、79、80、89、91、99。
Table 1 is compound prepared by the embodiment of the present invention and compares the characteristics of luminescence test of the luminescent device of substance preparation As a result.
The characteristics of luminescence of [table 1] luminescent device is tested
The above result shows that benzidine compound of the invention is 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 present invention improvement on various forms or details, these improvement also fall into this hair In bright protection domain.

Claims (9)

1. a kind of benzidine compound, which is characterized in that general formula of molecular structure is as shown in chemical formula I：
Wherein, Ra、RbIndependently selected from hydrogen, substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C25 virtues Base, Ra、RbThe two can connect cyclization；
Ar1、Ar2、Ar3、Ar4Any one in following group：
Any one of L in following group：
R1、R2、R3、R4、R5Independently selected from H, cyano, halogen atom, substituted or unsubstituted C1~C10 alkyl, substitution or not One kind in substituted C6~C25 aryl, substituted or unsubstituted C3~C18 heteroaryls；R6、R7、R8、R9、R10, R independently selects It is miscellaneous from substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C25 aryl, substituted or unsubstituted C3~C18 One kind in aryl.
2. a kind of benzidine compound according to claim 1, which is characterized in that its structure is in formula II-IV Any one：
3. a kind of benzidine compound according to claim 1, which is characterized in that Ar1、Ar2、Ar3、Ar4Independently selected from Any one in group as follows：
Any one of L in following group：
R1、R2、R3、R4、R5Independently selected from H, cyano, halogen atom or substituted or unsubstituted following group：C1~C6 alkyl, Phenyl, naphthalene, anthryl, phenanthryl, pyrenyl, fluorenyl, two fluorenyl of spiral shell, carbazyl, pyridyl group, pyrimidine radicals, phenothiazinyl, phenoxazines In base, acridinyl, dibenzothiophene, dibenzofuran group, benzothienyl, benzofuranyl, quinolyl or isoquinolyl One kind；
R6、R7, R is independently selected from substituted or unsubstituted following group：C1~C4 alkyl, phenyl, naphthalene, anthryl, phenanthryl, pyrene Base, fluorenyl, carbazyl, pyridyl group, pyrimidine radicals, phenothiazinyl, phenoxazine groups, acridinyl, dibenzothiophene, dibenzofurans One kind in base, benzothienyl, benzofuranyl.
4. a kind of benzidine compound according to claim 1, which is characterized in that Ar1、Ar2、Ar3、Ar4In it is at least one Selected from group as follows：
5. a kind of benzidine compound according to claim 1, which is characterized in that R is selected from methyl, ethyl, isopropyl, uncle Any one in butyl, substituted or unsubstituted phenyl.
6. a kind of benzidine compound according to claim 1, which is characterized in that R1、R2、R3、R4、R5Independently selected from H Or substituted or unsubstituted following group：C1~C4 alkyl, phenyl, naphthalene, anthryl, phenanthryl, pyrenyl, fluorenyl, two fluorenyl of spiral shell, click Oxazolyl, pyridyl group, phenothiazinyl, phenoxazine groups, acridinyl, dibenzothiophene, dibenzofuran group, benzothienyl, benzene And any one in furyl；R6、R7, R do not take independently selected from C1~C4 alkyl, substituted or unsubstituted phenyl, substitution or Any one in the naphthalene in generation.
7. a kind of benzidine compound according to claim 1, which is characterized in that in chemical constitution as follows Any one：
8. 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 contain claim 1~7 any one of them connection Aniline compound.
9. according to a kind of organic luminescent device described in claim 8, which is characterized in that the organic matter layer includes that hole passes Defeated layer contains claim 1~7 any one of them benzidine compound in hole transmission layer.
CN201810789208.4A 2018-07-18 2018-07-18 A kind of benzidine compound and its organic luminescent device Withdrawn CN108752261A (en)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109400520A (en) * 2018-11-27 2019-03-01 长春海谱润斯科技有限公司 A kind of benzidine compound and its organic electroluminescence device
CN112047872A (en) * 2020-09-18 2020-12-08 吉林奥来德光电材料股份有限公司 Organic electroluminescent fluorene compound and preparation method and application thereof
WO2021141382A1 (en) * 2020-01-08 2021-07-15 주식회사 엘지화학 Fluorene-based compound, organic light-emitting device using same, and manufacturing method therefor
CN113443999A (en) * 2021-08-02 2021-09-28 河北凡克新材料有限公司 Benzene liquid crystal compound and preparation method thereof
CN113563898A (en) * 2021-08-02 2021-10-29 河北凡克新材料有限公司 Liquid crystal compound and preparation method and application thereof

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109400520A (en) * 2018-11-27 2019-03-01 长春海谱润斯科技有限公司 A kind of benzidine compound and its organic electroluminescence device
WO2021141382A1 (en) * 2020-01-08 2021-07-15 주식회사 엘지화학 Fluorene-based compound, organic light-emitting device using same, and manufacturing method therefor
JP2023505978A (en) * 2020-01-08 2023-02-14 エルジー・ケム・リミテッド Fluorene-based compound, organic light-emitting device using the same, and method for producing the same
JP7403912B2 (en) 2020-01-08 2023-12-25 エルジー・ケム・リミテッド Fluorene compound, organic light-emitting device using the same, and method for producing the same
CN112047872A (en) * 2020-09-18 2020-12-08 吉林奥来德光电材料股份有限公司 Organic electroluminescent fluorene compound and preparation method and application thereof
CN112047872B (en) * 2020-09-18 2022-03-08 吉林奥来德光电材料股份有限公司 Organic electroluminescent fluorene compound and preparation method and application thereof
CN113443999A (en) * 2021-08-02 2021-09-28 河北凡克新材料有限公司 Benzene liquid crystal compound and preparation method thereof
CN113563898A (en) * 2021-08-02 2021-10-29 河北凡克新材料有限公司 Liquid crystal compound and preparation method and application thereof

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Application publication date: 20181106