CN108276326A - Compounds and organic luminescent device comprising it - Google Patents

Compounds and organic luminescent device comprising it Download PDF

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Publication number
CN108276326A
CN108276326A CN201810001702.XA CN201810001702A CN108276326A CN 108276326 A CN108276326 A CN 108276326A CN 201810001702 A CN201810001702 A CN 201810001702A CN 108276326 A CN108276326 A CN 108276326A
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unsubstituted
substituted
compound
layer
aryl
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咸昊完
安贤哲
姜京敏
金熙宙
金东骏
闵丙哲
金槿泰
李萤振
林东焕
林大喆
权桐热
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Dongjin Semichem Co Ltd
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Dongjin Semichem Co Ltd
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Abstract

The present invention relates to the novel aryl amine compounds for having imported carbazole and diaryl fluorene structure and comprising its organic luminescent device.

Description

Compounds and organic luminescent device comprising it
Technical field
The present invention relates to compounds and include its organic luminescent device.
Background technology
In Organic Light Emitting Diode, the material as organic matter layer can be broadly dassified into luminescent material, sky according to function Hole injection material, hole transporting material, electron transport materials, electron injection material etc..Also, above-mentioned luminescent material can according to point Son amount is classified as macromolecule and low molecule, and the phosphor of the singlet excited state from electronics can be classified as according to luminescence mechanism The phosphor material of material and tri-state excited state from electronics, luminescent material can be classified as blue, green, red according to illuminant colour Yellow needed for color luminescent material and the better natural colour of embodiment and orange light emitting materials.Also, in order to increase excitation purity, and lead to It crosses energy transfer and increases luminous efficiency, main body/dopant class can be used as luminescent substance.If its principle is that will be sent out with main composition The main body of photosphere is compared, and the dopant that band gap is small and luminous efficiency is outstanding is mixed in auxiliary layer on a small quantity, then is produced in main body Raw exciton is conveyed to dopant, to send out efficient light.At this point, the wavelength of main body is moved to the wavelength band of dopant, The light of wavelength needed for can thus being obtained according to the type of the dopant and main body utilized.
So far, as the substance for being used in this organic luminescent device, well-known there are many compounds, but are utilizing So far it in the case of the organic luminescent device of well-known substance, due to high driving voltage, low efficiency and short life, holds It is continuous to require to develop new material.Therefore, ongoing effort using the substance with outstanding characteristic come develop with low voltage drive, High brightness and the organic luminescent device of long-life.
Existing technical literature
Patent document
Japanese Laid-Open Patent 10-2015-530735
Invention content
The present invention provides novel organic compound and the organic luminescent device comprising it.
But problem to be solved by this invention is not limited to problem described above, the technical field of the invention Those of ordinary skill can be clearly understood that the other problems not described according to contents below.
The first embodiment of the present invention provides the compound indicated by following formula 1.
Chemical formula 1
In above-mentioned chemical formula 1, R1To R5It is separately hydrogen, heavy hydrogen, substituted or unsubstituted C1-C6Alkyl, substitution Or unsubstituted C1-C6Alkoxy, substituted or unsubstituted C2-C6Alkenyl, substituted or unsubstituted C6-C30Aryl or substitution or Unsubstituted C5-C30Heteroaryl, R and R' are separately hydrogen, heavy hydrogen, substituted or unsubstituted C1-C6Alkyl, substitution or not Substituted C1-C6Alkoxy, substituted or unsubstituted C2-C6Alkenyl, substituted or unsubstituted C6-C30Aryl or substitution do not take The C in generation5-C30Heteroaryl, Ar, Ar1And Ar2It is separately substituted or unsubstituted C6-C30Aryl is substituted or unsubstituted C5-C30Heteroaryl, L are direct-coupling, C6-C30Arlydene or C5-C30The integer that heteroarylidene, l and o are 0 to 4, m are 0 or 1 Integer, the integer that n is 0 to 3.
Second embodiment of the present invention provides the organic luminescent device for including the compound of the present invention.
Present invention offer has imported carbazole and the novel aryl amine of diaryl fluorene structure, specifically, by carbazole second It position and is applicable in arylamine instead of the fluorenes first position of aryl or the 4th position and combines, form deep highest occupied molecular orbital (HOMO), it is formed simultaneously high lowest unoccupied molecular orbital (LUMO), and cavity conveying is improved by quick hole flow Characteristic realizes low-voltage, high efficiency, long-life organic luminescent device, and provide drive with high Tg to can inhibit phenomenon of roll-offing Stability when dynamic.
By the way that the compound of the present invention is suitable for the auxiliary layer that shines, the highest that formation was readily injected into and conveyed hole occupies Molecular orbit, while high lowest unoccupied molecular orbital is maintained, so that electron-block becomes easy, thus it is effectively formed auxiliary layer Interior exciton, to realize high efficiency organic luminescent device.Also, diaryl fluorene first position or the 4th position and virtue can be passed through The combination of base amine maintains high T1, so that when being applicable in phosphorescent devices, high efficiency is also presented, because of the film and interface arrangement of molecule It is outstanding, it can be achieved that quick hole flow, inhibition is roll-offed phenomenon, and realizes long lived devices, high Tg can be maintained, to prevent The recrystallization of film, to increase driving stability.
The compound of the present invention has the effect of high luminous efficiency, high excitation purity etc., to be suitable for organic light emission Device, solar power generation organic optical device etc., thus can greatly contribute to organic hair of flexible display, lighting apparatus etc. Optical diode (OLED) industry.
Description of the drawings
Fig. 1 shows the schematic diagrams of the organic luminescent device of an example of the invention.
The explanation of reference numeral
100：Substrate
200：Hole injection layer
300：Hole transporting layer
400：Luminescent layer
500：Electron supplying layer
600：Electron injecting layer
1000：Anode
2000：Cathode
Specific implementation mode
Hereinafter, with reference to attached drawing, the example and embodiment that the present invention will be described in detail so that the technical field of the invention it is general Logical technical staff can be easy to implement.
But the present invention can by it is a variety of it is different in the form of realize, and be not limited to example described herein and embodiment. Also, the part unrelated with explanation is omitted, in the specification, for similar in the figure in order to clearly state the present invention Part, be labelled with similar reference numeral.
In description of the invention full text, when a component is located at another component "upper", include not only component with The case where another component is in contact further includes the presence of the case where other component between the two parts.
In description of the invention full text, when one structural element of a part " comprising ", unless there are especially opposite It records, then means to may also include other structures element, rather than exclude other structures element.In description of the invention full text The term " about " that uses, " substantial " etc. when prompting intrinsic preparation and substance tolerance in mentioned meaning with its numerical value or Meaning close to its numerical value uses, and is undeservedly utilized with the infringer for preventing against one's conscience and is referred to help to understand the present invention The disclosure of accurate or absolute numerical value.Description of the invention full term "~() step " used herein or "~ Step " do not mean that " for~the step of ".
In description of the invention full text, " combination thereof " contained in the performance of Markush (Markush) form this One term means one or more of the group that recorded multiple structural elements in the performance by Markush form form Mixing or combination, it is meant that include selected from one or more of the group being made of above-mentioned multiple structural elements.
In description of the invention full text, " A and/or B " this record means " A or B or A and B ".
In description of the invention full text, term " aryl " means to include C6-30Aromatic cyclic hydrocarbon group, for example, benzene Base, benzyl, naphthalene, xenyl, terphenyl, fluorenyl, phenanthryl, triphenyl alkenyl, phenylakenyl,Base, fluorane thiophene first Base, benzo fluorenyl, benzo triphenyl alkenyl, benzoThe aromatic ring of base, anthryl, stilbenyl, pyrenyl etc., " heteroaryl Base " is as the C for including at least one miscellaneous element5-30Aromatic ring, such as, it is meant that comprising from pyrrolinyl, pyrazinyl, pyrrole Piperidinyl, indyl, isoindolyl, furyl, benzofuranyl, isobenzofuran-base, dibenzofuran group, aisaa benzothiophenyl, Dibenzo thiophenyl, quinolyl, isoquinolyl, quinoxalinyl, carbazyl, luxuriant and rich with fragrance cry base, acridinyl, phenanthroline, thienyl and By pyridine ring, pyridine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring, pyrrolidine ring, twoAlkane ring, Piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan nucleus, thiphene ring,Azoles ring,Diazole ring, benzoAzoles ring, thiazole The fragrance that ring, thiadiazole ring, benzothiazole ring, triazole ring, imidazole ring, benzimidazole ring, pyranoid ring, dibenzofurans ring are formed Race's heterocycle.
In description of the invention full text, term " alkyl " may include the saturated or unsaturated C of linear chain or branched chain1-C6Alkane Base, for example, may include methyl, ethyl, propyl, butyl, amyl, hexyl or their possible all isomers, but can not It is confined to this.
In description of the invention full text, in term " substituted or unsubstituted ", " substitution " mean can by be selected from by Heavy hydrogen, halogen, amino, itrile group, nitro, silylation, alkyl or C1~C20Alkyl, alkenyl or C2~C20Alkenyl, alkoxy Or C1~C20Alkoxy, naphthenic base or C3~C20Naphthenic base, Heterocyclylalkyl or C3~C20Heterocyclylalkyl or C5~C30's Aryl and C5~C30Heteroaryl composition one or more of group base substitution.
The first embodiment of the present invention provides the compound indicated by following formula 1.
Chemical formula 1
In above-mentioned chemical formula 1, R1To R5It is separately hydrogen, heavy hydrogen, substituted or unsubstituted C1-C6Alkyl, substitution Or unsubstituted C1-C6Alkoxy, substituted or unsubstituted C2-C6Alkenyl, substituted or unsubstituted C6-C30Aryl or substitution or Unsubstituted C5-C30Heteroaryl, R and R' are separately hydrogen, heavy hydrogen, substituted or unsubstituted C1-C6Alkyl, substitution or not Substituted C1-C6Alkoxy, substituted or unsubstituted C2-C6Alkenyl, substituted or unsubstituted C6-C30Aryl or substitution do not take The C in generation5-C30Heteroaryl, Ar, Ar1And Ar2It is separately substituted or unsubstituted C6-C30Aryl is substituted or unsubstituted C5-C30Heteroaryl, L are direct-coupling, C6-C30Arlydene or C5-C30The integer that heteroarylidene, l and o are 0 to 4, m are 0 or 1 Integer, the integer that n is 0 to 3.
In the example of the present invention, the compound of above-mentioned chemical formula 1 may include the chemical combination indicated by following formula 2 Object.
Chemical formula 2
In above-mentioned chemical formula 2, R1To R7It is separately hydrogen, heavy hydrogen, substituted or unsubstituted C1-C6Alkyl, substitution Or unsubstituted C1-C6Alkoxy, substituted or unsubstituted C2-C6Alkenyl, substituted or unsubstituted C6-C30Aryl or substitution or Unsubstituted C5-C30Heteroaryl, R and R' are separately hydrogen, heavy hydrogen, substituted or unsubstituted C1-C6Alkyl, substitution or not Substituted C1-C6Alkoxy, substituted or unsubstituted C2-C6Alkenyl, substituted or unsubstituted C6-C30Aryl or substitution do not take The C in generation5-C30Heteroaryl, Ar are substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C5-C30Heteroaryl, L are straight Meet coupling, C6-C30Arlydene or C5-C30Heteroarylidene.
In the example of the present invention, the compound of above-mentioned chemical formula 1 may include the chemical combination indicated by following formula 3 Object.
Chemical formula 3
In above-mentioned chemical formula 3, R1To R7It is separately hydrogen, heavy hydrogen, substituted or unsubstituted C1-C6Alkyl, substitution Or unsubstituted C1-C6Alkoxy, substituted or unsubstituted C2-C6Alkenyl, substituted or unsubstituted C6-C30Aryl or substitution or Unsubstituted C5-C30Heteroaryl, R and R' are separately hydrogen, heavy hydrogen, substituted or unsubstituted C1-C6Alkyl, substitution or not Substituted C1-C6Alkoxy, substituted or unsubstituted C2-C6Alkenyl, substituted or unsubstituted C6-C30Aryl or substitution do not take The C in generation5-C30Heteroaryl, Ar are substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C5-C30Heteroaryl.
In the example of the present invention, the compound of above-mentioned chemical formula 1 may include the chemical combination indicated by following formula 4 Object.
Chemical formula 4
In above-mentioned chemical formula 4, R1To R7It is separately hydrogen, heavy hydrogen, substituted or unsubstituted C1-C6Alkyl, substitution Or unsubstituted C1-C6Alkoxy, substituted or unsubstituted C2-C6Alkenyl, substituted or unsubstituted C6-C30Aryl or substitution or Unsubstituted C5-C30Heteroaryl, R and R' are separately hydrogen, heavy hydrogen, substituted or unsubstituted C1-C6Alkyl, substitution or not Substituted C1-C6Alkoxy, substituted or unsubstituted C2-C6Alkenyl, substituted or unsubstituted C6-C30Aryl or substitution do not take The C in generation5-C30Heteroaryl, Ar are substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C5-C30Heteroaryl, L are straight Meet coupling, C6-C30Arlydene or C5-C30Heteroarylidene.
The compound indicated by above-mentioned chemical formula 4 can reduce the driving voltage of organic luminescent device, and improve efficiency and longevity Life, in particular, long-life effect can be very outstanding.
In the example of the present invention, in above-mentioned chemical formula 1 to chemical formula 4, R3It can be selected from phenyl, xenyl, three In phenyl, fluorenyl, naphthalene, diphenylfluorene, dimethyl fluorene, phenanthryl, dibenzofurans, dibenzothiophenes and combination thereof, example Such as, it can be selected from phenyl, xenyl, diphenylfluorene, dimethyl fluorene and combination thereof.For example, above-mentioned R3Can be with selected from The phenyl that base in the group being made of naphthalene, dibenzofurans and dibenzothiophenes is connected or the diphenyl being connected with phenyl Fluorenes or the dimethyl fluorene being connected with phenyl.R3It is not limited to this, including selected from phenyl, xenyl, terphenyl, fluorenyl, naphthalene Base, diphenylfluorene, dimethyl fluorene, phenanthryl, dibenzofurans, dibenzothiophenes multiple bases a variety of connection structures.This feelings Under condition, in particular, the lowest unoccupied molecular orbital for being easy to block electronics can be maintained, and when deposition procedures, carried out with low temperature Control.
In the example of the present invention, in above-mentioned chemical formula 1 to chemical formula 4, Ar can be selected from phenyl, xenyl, three Phenyl, naphthalene, fluorenyl, diphenylfluorene, dimethyl fluorene, phenanthryl, triphenylene, dibenzofurans, dibenzothiophenes and they In combination.For example, above-mentioned Ar can be with selected from by terphenyl, naphthalene, phenanthryl, triphenylene, diphenylfluorene, dimethyl Fluorenes, dibenzofurans and dibenzothiophenes composition group in base be connected phenyl, be connected with phenyl diphenylfluorene, and Dimethyl fluorene, the dibenzofurans being connected with phenyl or the dibenzothiophenes being connected with phenyl that phenyl is connected.Ar is not It is confined to this, including selected from phenyl, xenyl, terphenyl, naphthalene, fluorenyl, diphenylfluorene, dimethyl fluorene, phenanthryl, triphenylene Base, dibenzofurans, dibenzothiophenes multiple bases a variety of connection structures.In this case, in particular, can maintain to be easy blocking The lowest unoccupied molecular orbital of electronics, and when deposition procedures, controlled with low temperature.
In the example of the present invention, the compound of above-mentioned chemical formula 1 can be as prepared in following formulas 1, but can not office It is limited to this.
Reaction equation 1
In the example of the present invention, above-mentioned organic luminescent compounds may include following compound, but can be not limited to this.
Second embodiment of the present invention provides the organic luminescent device for including the compound indicated by above-mentioned chemical formula 1. Above-mentioned organic luminescent device can include having for one layer or more containing the compounds of this invention between first electrode and second electrode Machine nitride layer.
In the example of the present invention, above-mentioned organic matter layer can be hole injection layer, hole transporting layer and the auxiliary that shines One layer or more in layer, for example, can be hole transporting layer or luminous auxiliary layer, but it can be not limited to this, at this point, the present invention Compound can be used alone or is used together with well known organic luminescent compounds.
The present invention an example in, above-mentioned organic luminescent device may include the organic matter layer containing cavity conveying substance and Organic matter layer containing the compound indicated by above-mentioned chemical formula 1, but can be not limited to this.
Above-mentioned organic luminescent device can include more than one hole between anode (anode) and cathode (cathode) Implanted layer (HIL), hole transporting layer (HTL), luminescent layer (EML), electron supplying layer (ETL), electron injecting layer (EIL) etc. have Machine nitride layer.
For example, above-mentioned organic luminescent device can be prepared according to structure recorded in Fig. 1.Organic luminescent device can To it is lower and on stack gradually anode (hole injecting electrode 1000)/200/ hole transporting layer of hole injection layer, 300/ auxiliary layer 400/ 500/ electron injecting layer of electron supplying layer, 600/ cathode (electron injection electrode 2000).
In Fig. 1, the substrate for organic luminescent device can be used in substrate 100, in particular, can be mechanical strength, hot steady Qualitative, transparent, surface smoothness, ease of handling and the outstanding transparent glass substrate or flexible plastic base of water proofing property Plate.
Hole injecting electrode 1000 is used as the anode in the hole for being injected with machine luminescent device.In order to which hole can be injected, It, can be by tin indium oxide (ITO), indium zinc oxide (IZO), graphene (graphene) etc using the substance with low work function Transparent material formed.
By vacuum deposition method, spin-coating method, casting, LB (Langmuir-Blodgett) method etc. come in above-mentioned anode electricity Pole overburden hole injection layer substance, thus can form hole injection layer 200.Sky is being formed by above-mentioned vacuum deposition method In the case of the implanted layer of cave, sedimentary condition because as hole injection layer material compound, needed for hole injection layer knot Structure and thermal characteristics etc. and it is different, but usually can 50-500 DEG C depositing temperature, 10-8To 10-3The vacuum degree of support, 0.01 toDeposition velocity,It is suitably selected within the scope of to 5 μm of layer thickness.
Then, by vacuum deposition method, spin-coating method, casting, LB methods etc. come in 200 overburden of above-mentioned hole injection layer Thus hole transporting layer substance can form hole transporting layer 300.Hole transporting layer is being formed by above-mentioned vacuum deposition method In the case of, sedimentary condition is different due to the compound used, but typically it will be preferred to, the formation with hole injection layer almost It is selected in identical condition and range.Above-mentioned hole transporting layer can be more than one, for example, can be the first cavity conveying Two layers of layer and the second hole transporting layer (luminous auxiliary layer).It in above-mentioned first hole transporting layer and the second hole transporting layer One may include the compound of the chemical formula 1 of the present invention.
Later, by vacuum deposition method, spin-coating method, casting, LB methods etc. come auxiliary in above-mentioned hole transporting layer overburden A layer substance is helped, auxiliary layer 400 thus can be formed.It in the case of forming auxiliary layer, is deposited by above-mentioned vacuum deposition method Condition is different due to the compound used, but typically it will be preferred to, in the condition and range almost the same with the formation of hole injection layer Inside selected.Also, well known compound can be used as main body or dopant by above-mentioned auxiliary layer material.
Also, in the case of being used together with phosphorescent dopants in transfer layer, in order to prevent triplet excitons or hole to The phenomenon that electron supplying layer is spread can also be laminated hole by vacuum deposition method or spin-coating method and inhibit material (HBL).It can make at this time Hole inhibiting substances are not particularly limited, but can select arbitrary object from the well known substance for inhibiting material as hole Matter utilizes.For example, can enumerateOxadiazole derivative or triazole derivative, phenanthroline derivative or Japanese Unexamined Patent Publication 11- Recorded hole inhibits material etc. in 329734 (A1), typically, Balq (bis- (8- hydroxy-2-methylquinolines)-can be used Aluminium biphenyl phenates), phenanthroline (phenanthrolines) class compound (such as BCP (Basso of general purpose display (UDC) company Coupoline)) etc..
It is formed with electron supplying layer 500 on 400 top of auxiliary layer as formed above, at this point, above-mentioned electron supplying layer can lead to The methods of vacuum deposition method, spin-coating method, casting are crossed to be formed.Also, the sedimentary condition of above-mentioned electron supplying layer is because using Compound and it is different, but typically it will be preferred to, selected in the condition and range almost the same with the formation of hole injection layer.
Later, electron injecting layer 600 can be formed in 500 overburden electron injecting layer substance of above-mentioned electron supplying layer, At this point, above-mentioned electron supplying layer can form conventional electron injection by the method for vacuum deposition method, spin-coating method, casting etc. Layer substance.
This can be used in hole injection layer 200, hole transporting layer 300, auxiliary layer 400, the electron supplying layer 500 of above-mentioned device The compound of invention or following substance, alternatively, the compound of the present invention and well known substance can be used together.
The moon for injecting electronics is formed on electron injecting layer 600 by the method for vacuum deposition method or sputtering method etc. Pole 2000.As cathode, various metals can be used.Concrete example has the substance of aluminium, gold, silver etc..
Anode, hole injection layer, hole transporting layer, auxiliary layer, electricity not only may be used in the organic luminescent device of the present invention The knot of the organic luminescent device of various structures also can be used in the organic luminescent device of sub- transfer layer, electron injecting layer, cathode construction Structure can also form the middle layer of one or two layers as needed.
As described above, the thickness of each organic matter layer formed according to the present invention can be adjusted according to required degree Section, it is preferable that be specially 10 to 1000nm, more specifically 20 to 150nm.
Also, in the present invention, including the organic matter layer of the compound indicated by above-mentioned chemical formula 1 can be by organic matter layer Thickness is adjusted to molecular unit, thus has the advantages that surface is uniform and morphological stability protrudes.
For the organic luminescent compounds of present embodiment, what the applicable first embodiment for the present invention was recorded Content, but can be not limited to this.
Hereinafter, embodiment through the invention carries out more specific description, the scope of the present invention is not limited to the present embodiment.
Embodiment
Preparation example 1
The synthesis of OP
In order to synthesize purpose compound, synthesized by above-mentioned steps, to prepare OP.
The synthetic method of following OP1 is as follows.
In round-bottomed flask, by bromo- 9,9- diphenyl -9H- fluorenes (4-bromo-9, the 9-diphenyl-9H- of the 4- of 10.0g Fluorene), the aniline (aniline) of 2.6g, 3.6g t-BuONa, 0.9g Pd2(dba)3, 1.1ml (t-Bu)3P is molten Solution is in the toluene of 130ml, later, flows back, is stirred on one side on one side.Confirm reaction using thin-layered chromatography (TLC), And after adding water, reaction was completed.Organic layer is extracted using methylcellulose (MC), and after being filtered under diminished pressure, carried out Column purification and recrystallization obtain the OP1 of 7.01g (yield 68%).
Change initial substance in method identical with above-mentioned OP1 to have synthesized following OP2 to OP9.
Synthesis example 1：The synthesis of compound 1
In round-bottomed flask, by the bromo- 9- phenyl -9H- carbazoles (2-bromo-9-phenyl-9H- of the 2- of 5.0g Carbazole), the Pd of t-BuONa, 0.6g of OP1,2.2g of 7.0g2(dba)3, 0.7ml (t-Bu)3P is dissolved in 120ml Toluene flow back on one side later, be stirred on one side.Confirm reaction using thin-layered chromatography, and after adding water, Reaction was completed.Organic layer is usually extracted using Methyl cellulose, and after being filtered under diminished pressure, carries out column purification and recrystallization to obtain Obtained the compound 1 of 7.07g (yield 70%).
m/z：650.27 (100.0%), 651.28 (53.4%), 652.28 (14.0%), 653.28 (2.4%)
Synthesis example 2：The synthesis of compound 2
OP1 is replaced using OP2, and to have synthesized compound 2 (yield 68%) with 1 identical method of compound.
m/z：726.30 (100.0%), 727.31 (59.9%), 728.31 (17.6%), 729.31 (3.4%)
Synthesis example 3：The synthesis of compound 3
OP1 is replaced using OP3, and to have synthesized compound 3 (yield 62%) with 1 identical method of compound.
m/z：726.30 (100.0%), 727.31 (59.9%), 728.31 (17.6%), 729.31 (3.4%)
Synthesis example 4：The synthesis of compound 4
OP1 is replaced using OP4, and to have synthesized compound 4 (yield 65%) with 1 identical method of compound.
m/z：726.30 (100.0%), 727.31 (59.9%), 728.31 (17.6%), 729.31 (3.4%)
Synthesis example 5：The synthesis of compound 5
OP1 is replaced using OP5, and to have synthesized compound 5 (yield 70%) with 1 identical method of compound.
m/z：766.33 (100.0%), 767.34 (63.2%), 768.34 (20.1%), 769.34 (4.0%)
Synthesis example 6：The synthesis of compound 6
OP1 is replaced using OP6, and to have synthesized compound 6 (yield 70%) with 1 identical method of compound.
m/z：726.30 (100.0%), 727.31 (59.9%), 728.31 (17.6%), 729.31 (3.4%)
Synthesis example 7：The synthesis of compound 7
Utilize 9- ([1,1'- xenyls] -4- bases) bromo- 9H- carbazoles of -2- (9- ([1,1'-biphenyl] -4-yl) -2- Bromo-9H-carbazole the bromo- 9- phenyl -9H- carbazoles of 2- are replaced), and to have synthesized change with 1 identical method of compound Close object 7 (yield 63%).
m/z：726.30 (100.0%), 727.31 (59.9%), 728.31 (17.6%), 729.31 (3.4%)
Synthesis example 8：The synthesis of compound 8
OP1 is replaced using OP7, and to have synthesized compound 8 (yield 60%) with 1 identical method of compound.
m/z：650.27 (100.0%), 651.28 (53.4%), 652.28 (14.0%), 653.28 (2.4%)
Synthesis example 9：The synthesis of compound 9
OP1 is replaced using OP8, and to have synthesized compound 9 (yield 59%) with 1 identical method of compound.
m/z：726.30 (100.0%), 727.31 (59.9%), 728.31 (17.6%), 729.31 (3.4%)
Synthesis example 10：The synthesis of compound 10
OP1 is replaced using OP9, and to have synthesized compound 10 (yield 63%) with 1 identical method of compound.
m/z：726.30 (100.0%), 727.31 (59.9%), 728.31 (17.6%), 729.31 (3.4%)
Preparation example 2：The preparation of organic luminescent device
By distilled water ultrasonic wave toThickness tin indium oxide be applied as to the glass substrate of film wash It washs.If distillation water washing terminates, ultrasonic washing is carried out using the solvent of isopropanol, acetone, methanol etc., and be dried Later, it is transferred to plasma cleaner, after then cleaning aforesaid substrate 5 minutes using oxygen plasma, in tin indium oxide Substrate top utilizes thermal vacuum depositor (thermal evaporator), will as hole injection layerDNTPD carry out Film, willHATCN be filmed, as hole transporting layer willBAP be filmed, as luminous auxiliary layer It willCompound 1 be filmed after, as above-mentioned auxiliary layer doping 3% BH01：BD01, withIt is made Film.It then, will as electron supplying layerET01：Liq(1：It 1), will after being filmedLiF,'s Aluminium (Al) is filmed, and by the device sealing (Encapsulation) in glove box, to be prepared for organic luminescent device (embodiment 1).
In the manner compound is replaced using compound 2 to compound 10 (embodiment 2 to embodiment 10) 1, to be prepared for organic luminescent device.
Comparative example
Compound 1 is replaced using following Ref.1 to Ref.7 (comparative example 1 to comparative example 7), in addition to this, with above-mentioned system Standby example 2 is prepared for organic luminescent device in the same manner.
Experimental example 1：The performance evaluation of organic luminescent device
Apply electricity using 2400 source measuring unit of Keithley (Kiethley 2400source measurement unit) It presses to inject electronics and hole, is measured using Konica Minolta (Konica Minolta) spectroradiometer (CS-2000) Thus under atmospheric conditions brightness when shining is measured for applying alive current density and brightness, to have rated reality The performance of the organic luminescent device of example and comparative example is applied, and the results are shown in table 1.
Table 1
As shown in Table 1 above, it is seen that multiple embodiments of the invention are compared with comparative example 1 to comparative example 7, efficiency and service life Rise, and can confirm that physical property is outstanding in all respects.If comparing the embodiment of the present invention, understand to consider following several feelings In the compound of the present invention of condition, the driving voltage of organic luminescent device is low, and efficiency and service life substantially improve, i.e.,：With comparative example 2, comparative example 3, comparative example 6, comparative example 7 are compared, deep to be formed in conjunction with carbazole second and diphenylfluorene 1, the 4th position The case where highest occupied molecular orbital, compared with comparative example 1, comparative example 4, comparative example 5, so that Tg is become because diphenylfluorene replaces Height, to inhibit the phenomenon that the recrystallization of film, compared with comparative example 2, comparative example 3, comparative example 6, because of diphenylfluorene first Or the 4th substitution and form film, and interface arrangement is made to become outstanding, to have quick hole flow (hole Mobility) the case where.
The being illustrative for property of explanation of aforementioned present invention, general technical staff of the technical field of the invention can manage Solution can be easily deformed in other specific ways in the case where not changing the technological thought or essential feature of the present invention.Therefore, It should be understood that various embodiments described above is illustrative in all respects, without being restrictive.For example, being said with single type Bright each structural element is implemented dispersiblely, and equally, illustrating also can be in a manner of combination for multiple structural elements of dispersion Implement.
Range Representation, rather than above-mentioned detailed description, patent is claimed by appended patented invention in the scope of the present invention The meaning of range is claimed in invention and range and the mode that has altered or deform derived from its equivalents should be by It is construed to be included within the scope of the present invention.

Claims (11)

1. a kind of compound, which is characterized in that it is indicated by following formula 1,
Chemical formula 1
In above-mentioned chemical formula,
R1To R5It is separately hydrogen, heavy hydrogen, substituted or unsubstituted C1-C6Alkyl, substituted or unsubstituted C1-C6Alcoxyl Base, substituted or unsubstituted C2-C6Alkenyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C5-C30Heteroaryl,
R and R' is separately hydrogen, heavy hydrogen, substituted or unsubstituted C1-C6Alkyl, substituted or unsubstituted C1-C6Alkoxy, Substituted or unsubstituted C2-C6Alkenyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C5-C30Heteroaryl,
Ar、Ar1And Ar2It is separately substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C5-C30Heteroaryl,
L is direct-coupling, C6-C30Arlydene or C5-C30Heteroarylidene,
The integer that l and o is 0 to 4, the integer that m is 0 or 1, the integer that n is 0 to 3.
2. compound according to claim 1, which is characterized in that
Above compound includes the compound indicated by following formula 2,
Chemical formula 2
In above-mentioned chemical formula,
R1To R7It is separately hydrogen, heavy hydrogen, substituted or unsubstituted C1-C6Alkyl, substituted or unsubstituted C1-C6Alcoxyl Base, substituted or unsubstituted C2-C6Alkenyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C5-C30Heteroaryl,
R and R' is separately hydrogen, heavy hydrogen, substituted or unsubstituted C1-C6Alkyl, substituted or unsubstituted C1-C6Alkoxy, Substituted or unsubstituted C2-C6Alkenyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C5-C30Heteroaryl,
Ar is substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C5-C30Heteroaryl,
L is direct-coupling, C6-C30Arlydene or C5-C30Heteroarylidene.
3. compound according to claim 1, which is characterized in that
Above compound includes the compound indicated by following formula 3,
Chemical formula 3
In above-mentioned chemical formula,
R1To R7It is separately hydrogen, heavy hydrogen, substituted or unsubstituted C1-C6Alkyl, substituted or unsubstituted C1-C6Alcoxyl Base, substituted or unsubstituted C2-C6Alkenyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C5-C30Heteroaryl,
R and R' is separately hydrogen, heavy hydrogen, substituted or unsubstituted C1-C6Alkyl, substituted or unsubstituted C1-C6Alkoxy, Substituted or unsubstituted C2-C6Alkenyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C5-C30Heteroaryl,
Ar is substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C5-C30Heteroaryl.
4. compound according to claim 1, which is characterized in that
Above compound includes the compound indicated by following formula 4,
Chemical formula 4
In above-mentioned chemical formula,
R1To R7It is separately hydrogen, heavy hydrogen, substituted or unsubstituted C1-C6Alkyl, substituted or unsubstituted C1-C6Alcoxyl Base, substituted or unsubstituted C2-C6Alkenyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C5-C30Heteroaryl,
R and R' is separately hydrogen, heavy hydrogen, substituted or unsubstituted C1-C6Alkyl, substituted or unsubstituted C1-C6Alkoxy, Substituted or unsubstituted C2-C6Alkenyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C5-C30Heteroaryl,
Ar is substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C5-C30Heteroaryl,
L is direct-coupling, C6-C30Arlydene or C5-C30Heteroarylidene.
5. compound according to any one of claim 1 to 4, which is characterized in that R3Selected from phenyl, xenyl, terphenyl In base, phenanthryl, fluorenyl, naphthalene, diphenylfluorene, dimethyl fluorene, dibenzofurans, dibenzothiophenes and combination thereof.
6. compound according to any one of claim 1 to 4, which is characterized in that Ar is selected from phenyl, xenyl, three Phenyl, naphthalene, fluorenyl, diphenylfluorene, dimethyl fluorene, phenanthryl, triphenylene, dibenzofurans, dibenzothiophenes and they In combination.
7. compound according to claim 1, which is characterized in that
Above compound includes following compound,
8. a kind of organic luminescent device, which is characterized in that organic including one layer or more between first electrode and second electrode Nitride layer, above-mentioned organic matter layer include compound described in claim 1.
9. organic luminescent device according to claim 8, which is characterized in that above-mentioned organic matter layer is hole injection layer, sky One layer or more in cave transfer layer and luminous auxiliary layer.
10. organic luminescent device according to claim 8, which is characterized in that above-mentioned organic luminescent device includes：
Include the organic matter layer of cavity conveying substance；And
Include the organic matter layer of the compound indicated by chemical formula 1 described in claim 1.
11. organic luminescent device according to claim 10, which is characterized in that include the change indicated by above-mentioned chemical formula 1 The organic matter layer for closing object is the auxiliary layer that shines.
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CN109232382B (en) * 2018-11-15 2021-12-28 长春海谱润斯科技股份有限公司 Carbazole derivative and organic electroluminescent device thereof

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