CN109206324A - Compounds and organic luminescent device comprising it - Google Patents
Compounds and organic luminescent device comprising it Download PDFInfo
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- CN109206324A CN109206324A CN201810733996.5A CN201810733996A CN109206324A CN 109206324 A CN109206324 A CN 109206324A CN 201810733996 A CN201810733996 A CN 201810733996A CN 109206324 A CN109206324 A CN 109206324A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds 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
- C07C211/61—Compounds 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds 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
- C07C211/60—Compounds 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 containing a ring other than a six-membered aromatic ring forming part of at least one of the condensed ring systems
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/156—Hole transporting layers comprising a multilayered structure
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- 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
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Abstract
The present invention relates to novel aryl amine compounds, if being used as hole transporting layer (HTL), shine auxiliary layer (HT prime) or hole injection layer (HIL), hole injection and conveying characteristic can then be increased, so as to provide the high efficiency and long-life effect of device.
Description
Technical field
The present invention relates to novel aryl amine compounds and include its organic luminescent device.
Background technique
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
Material and the triplet excitation state from electronics phosphor material, luminescent material can be classified as according to illuminant colour blue, green,
Yellow and orange light emitting materials needed for red illuminating material and the better natural colour of embodiment.Also, in order to increase excitation purity, and
Increase luminous efficiency by energy transfer, main body/dopant class can be used as luminescent substance.If its principle is will be with main composition
The main body of luminescent layer 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 in main body
The exciton of generation is conveyed to dopant, to issue high-efficient light.At this point, the wavelength of main body is moved to the wavelength band of dopant
It is dynamic, thus the light of required wavelength can be 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 where 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 developed using the substance with outstanding characteristic 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
Summary of the invention
The present invention provides compounds 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.
First embodiment of the invention provides the compound indicated by following formula 1.
Chemical formula 1
In above-mentioned chemical formula 1,
Ar1To Ar4It is each independently substituted or unsubstituted C6~C30Aryl or substituted or unsubstituted C5~
C30Heteroaryl,
Ar5For substituted or unsubstituted C6~C10Aryl,
R、R`、R1And R2It is each independently hydrogen, substituted or unsubstituted C1~C30Alkyl, substituted or unsubstituted C2
~C30Alkenyl, substituted or unsubstituted C6~C30Aryl or substituted or unsubstituted C5~C30Heteroaryl,
L be 0 perhaps 1 to 4 integer m be 0 or integer of 1 to 3.
Second embodiment of the present invention provides the organic luminescent device comprising the compound of the present invention.
The present invention relates to the compounds for the arylamine for importing fluorene structured and linear aryl, specifically, fluorene structured and line
Property aryl and nitrogen Direct Bonding be easy to block electronics, pass through and expand linearly connected by forming deeper HOMO and high LUMO
4 or more aryl, increase conjugation and molecule film arrangement it is outstanding, thus can pass through quick hole flow
(hole mobility) can inhibit roll-off phenomenon and realization long lived devices.Also, it will be another in the aryl of arylamine
The aryl of side rather than the aryl of linearly connected, are fixed as C10Aryl below maintains HOMO and LUMO appropriate, high
T1 is effectively formed exciton, it can be achieved that high efficiency organic luminescent device in luminescent layer.Also, because of 4 or more virtues of linearly connected
Base has high Tg under lesser molecular weight, thus prevents recrystallizationization in driving, can increase the driving of device
Stability.
The compound of the present invention is used as hole transporting layer (HTL), shine auxiliary layer (HT prime) or hole injection layer
(HIL) when, hole injection and conveying characteristic can be increased, thus can provide the high efficiency and long-life effect of device.Of the invention
Compound can maintain high triplet energies, thus be presented high efficiency, the substituent group of reason 4 or more linear aryl compositions and
High Tg can be maintained, thin film stability and long-life effect thus can be presented in driving element.
The compound of the present invention has the effect of high luminous efficiency, the improvement of driving voltage and long-life, suitable for having
Machine luminescent device, solar power generation organic optical device etc., so as to the organic light-emitting diodes to flexible display, luminaire etc.
Tremendous contribution is made in pipe (OLED) industry.
Detailed description of the invention
Fig. 1 shows the schematic diagrams of the organic luminescent device of an example of the invention.
The explanation of appended drawing reference
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 embodiment
Hereinafter, referring to attached drawing, the example and embodiment that the present invention will be described in detail, so that the technical field of the invention 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 and embodiment described herein.
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 appended drawing reference.
In the full text of description of the invention, when a component is located at another component "upper", not only include component with
The case where another component is in contact, include thes case where there is other component between the two parts.
In the full text of description of the invention, 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 the full text of description of the invention
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.Term "~() step " used in the full text of description of the invention or "~
Step " do not mean that " for~the step of ".
In the full text of description of the invention, " their combination " contained in the performance of Markush (Markush) form this
One term means one or more of the group that documented multiple structural elements form in the performance by Markush form
Mixing or combination, it is meant that including selected from one or more of the group that is made of above-mentioned multiple structural elements.
In the full text of description of the invention, " A and/or B " this record means " A or B or A and B ".
In the full text of description of the invention, term " aryl " means comprising C6-30Aromatic cyclic hydrocarbon group, for example, benzene
Base, benzyl, naphthalene, xenyl, terphenyl, fluorenyl, phenanthryl, triphenyl alkenyl, phenylakenyl,Base, fluorane thenyl,
Benzo fluorenyl, benzo triphenyl alkenyl, benzoThe aromatic ring of base, anthryl, stilbenyl, pyrenyl etc., " heteroaryl "
As the C comprising at least one miscellaneous element5-30Aromatic ring, such as, it is meant that comprising from pyrrolinyl, pyrazinyl, pyridine
Base, indyl, isoindolyl, furyl, benzofuranyl, isobenzofuran-base, dibenzofuran group, aisaa benzothiophenyl, two
Aisaa benzothiophenyl, 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, dioxanes ring, piperazine
Phenazine ring, morpholine ring, piperazine ring, carbazole ring, furan nucleus, thiphene ring, oxazole ring, oxadiazoles ring, benzoxazoles ring, thiazole ring, thiophene
The aromatic series that diazonium ring, benzothiazole ring, triazole ring, imidazole ring, benzimidazole ring, pyranoid ring, dibenzofurans ring are formed is miscellaneous
Ring group.
In the full text of description of the invention, term " alkyl " may include the saturated or unsaturated C of linear chain or branched chain type1-C6
Alkyl, for example, may include methyl, ethyl, propyl, butyl, amyl, hexyl or their all isomers, it is likely that not by
It is limited.
In the full text of description of the invention, term " substituted or unsubstituted " refer to selected from by heavy hydrogen, halogen, amino,
Itrile group, nitro, silylation, alkyl or C1~C20Alkyl, alkenyl or C2~C20Alkenyl, alkoxy or C1~C20Alcoxyl
Base, naphthenic base or C3~C20Naphthenic base, Heterocyclylalkyl or C3~C20Heterocyclylalkyl or C5~C30Aryl or C5~C30's
The base of one or more of the group of heteroaryl composition is substituted or unsubstituted.
Also, in description of the invention full text, identical appended drawing reference can have as long as no the special content referred to
There is equivalent.
In the full text of description of the invention, term " fluorenes " may include hydrogen in conjunction with the 9th carbon by substituted or unsubstituted
C1-20Alkyl, substituted or unsubstituted C1-20Alkenyl, substituted or unsubstituted C5-30Aryl or substituted or unsubstituted
C3-30Heteroaryl replace the case where.
First embodiment of the invention provides the compound indicated by following formula 1:
Chemical formula 1
Ar1To Ar4It is each independently substituted or unsubstituted C6~C30Aryl or substituted or unsubstituted C5~
C30Heteroaryl,
Ar5For substituted or unsubstituted C6~C10Aryl,
R、R`、R1And R2It is each independently hydrogen, substituted or unsubstituted C1~C30Alkyl, substituted or unsubstituted C2
~C30Alkenyl, substituted or unsubstituted C6~C30Aryl or substituted or unsubstituted C5~C30Heteroaryl,
L be 0 perhaps 1 to 4 integer m be 0 or integer of 1 to 3.
In an example of the invention, above-mentioned Ar1To Ar4Phenyl, naphthalene or phenanthryl can be each independently.
In an example of the invention, by-Ar in chemical formula 11-Ar2-Ar3-Ar4The substituent group of expression can have one
Above meta position (meta) or ortho position (ortho) key.
In an example of the invention, above-mentioned Ar5It can be phenyl or naphthalene.
Also, in an example of the invention, above-mentioned Ar1To Ar4It can be each independently phenyl, naphthalene or phenanthryl, on
State Ar5It can be phenyl or naphthalene.
In an example of the invention, above-mentioned R and R` can be each independently methyl or phenyl.
In an example of the invention, above-mentioned R1And R2Hydrogen or phenyl can be each independently.
In an example of the invention, above compound can be indicated by following formula 2:
Chemical formula 2
In above-mentioned chemical formula 2,
Ar1To Ar4、R、R`、R1、R2, l and for example above-mentioned chemical formula 1 of m defined,
R3For hydrogen, substituted or unsubstituted C1~C30Alkyl or substituted or unsubstituted C2~C30Alkenyl,
The integer that n is 0 or 1 to 5.
In an example of the invention, above compound can be indicated by following formula 3:
Chemical formula 3
In the chemical formula 3,
Ar4、R1、R2, l and for example above-mentioned chemical formula 1 of m defined,
R3For hydrogen, substituted or unsubstituted C1~C30Alkyl or substituted or unsubstituted C2~C30Alkenyl,
The integer that n is 0 or 1 to 5,
Ar and Ar ' is each independently substituted or unsubstituted C6~C30Aryl,
R6To R8It is each independently hydrogen, substituted or unsubstituted C1~C30Alkyl, substituted or unsubstituted C2~C30's
Alkenyl, substituted or unsubstituted C6~C30Aryl or substituted or unsubstituted C5~C30Heteroaryl.
In an example of the invention, above compound can be indicated by following formula 4:
Chemical formula 4
In the chemical formula 4,
R1、R2, l and for example above-mentioned chemical formula 1 of m defined,
R3For hydrogen, substituted or unsubstituted C1~C30Alkyl or substituted or unsubstituted C2~C30Alkenyl,
The integer that n is 0 or 1 to 5,
R4And R5It is each independently hydrogen, substituted or unsubstituted C1~C30Alkyl, substituted or unsubstituted C2~C30's
Alkenyl, substituted or unsubstituted C6~C30Aryl or substituted or unsubstituted C5~C30Heteroaryl,
R6To R9It is each independently hydrogen, substituted or unsubstituted C1~C30Alkyl, substituted or unsubstituted C2~C30's
Alkenyl, substituted or unsubstituted C6~C30Aryl or substituted or unsubstituted C5~C30Heteroaryl.
In an example of the invention, R3It can be hydrogen or, n can be 0.
In an example of the invention, above-mentioned R4To R9It can be hydrogen.
In an example of the invention, the compound indicated by above-mentioned chemical formula 1 can be according to the reaction of such as following formulas 1
It is synthesized, it is likely that not limited to this:
Reaction equation 1
In above-mentioned reaction equation,
Ar1To Ar5、R、R`、R1、R2, l and for example above-mentioned chemical formula 1 of m defined.
It may include following compound by the compound that above-mentioned chemical formula 1 indicates in an example of the invention, it is likely that
It is confined to this:
For example, may include following compound by the compound that above-mentioned chemical formula 1 indicates, which makes to be condensed base minimum
Change, thus can maintain higher T1, exciton confinement effect in the luminescent layer that can maximize:
Second embodiment of the present invention provides the organic luminescent device of the compound comprising being 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 an example of the 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 the auxiliary layer that shines, it is likely that being not limited except as, at this point, the compound of the present invention can
It is used alone or is used together with well known organic luminescent compounds.
In the present invention, luminous auxiliary layer refers to the layer being formed between hole transporting layer and luminescent layer, defeated according to hole
Send the quantity of layer, also referred to as the second hole transporting layer or third hole transporting layer etc..
In an example of the invention, 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, it is likely that being not limited except as.
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. are organic
Nitride layer.
For example, above-mentioned organic luminescent device can be prepared according to structure documented 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/ luminescent 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 is can be used in substrate 100, in particular, can be steady for mechanical strength, heat
Qualitative, transparent, surface smoothness, ease of handling and the outstanding transparent glass substrate or flexible plastic base of waterproofness
Plate.
Hole injecting electrode 1000 is used as the anode for being injected with the hole of 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 where the implanted layer of cave, sedimentary condition because be used 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 torr (support),
0.01 toDeposition velocity,It is suitably selected in 5 μm of layer thickness range.
Then, by vacuum deposition method, spin-coating method, casting, LB method etc. come in above-mentioned 200 overburden of 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
Layer and two layers of the second hole transporting layer (luminous auxiliary layer).In above-mentioned first hole transporting layer and the second hole transporting layer extremely
Few one layer may include chemical formula 1 of the present invention compound.
Then, it by the methods of vacuum deposition method, spin-coating method, casting, LB method, in above-mentioned hole transporting layer or shines auxiliary
Depositing light emitting layer substance on layer is helped, luminescent layer 400 thus can be formed.In the feelings for forming luminescent layer by above-mentioned vacuum deposition method
Under condition, sedimentary condition is different due to the compound used, but typically it will be preferred to, in the almost phase of the formation with hole injection layer
It is selected in same condition and range.Also, well known compound can be used as main body or dopant by above-mentioned emitting layer material.
Also, in the case where being used together in luminescent layer with phosphorescent dopants, triplet exciton or hole in order to prevent
The phenomenon that spreading to electron supplying layer can also be laminated hole by vacuum deposition method or spin-coating method and inhibit material (HBL).At this time may be used
The hole inhibiting substances used are not particularly limited, but selection in the well known substance of material can be inhibited any from hole is used as
Substance utilizes.For example, oxadiazole derivatives or triazole derivative, phenanthroline derivative or Japanese Unexamined Patent Publication 11- can be enumerated
Documented hole inhibits material etc. in 329734 (A1), typically, can be used Balq (bis- (8- hydroxy-2-methylquinolines)-
Aluminium biphenyl phenates), phenanthroline (phe nanthrolines) 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 luminescent 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 above-mentioned 500 overburden electron injecting layer substance of 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, luminescent 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 yin 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..
Organic luminescent device of the invention can not only use anode, hole injection layer, hole transporting layer, luminescent layer, electricity
Sub- transfer layer, electron injecting layer, cathode construction organic luminescent device, the knot of the organic luminescent device of various structures also can be used
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, the organic matter layer in the present invention, comprising the above compound indicated by 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 is prominent.
It is applicable that first embodiment of the invention recorded for the organic luminescent compounds of present embodiment
Content, it is likely that being not limited except as.
Hereinafter, embodiment through the invention carries out more specific description, the scope of the present invention is not limited to the present embodiment.
Embodiment
The synthesis of preparation example 1.IM
In order to synthesize purpose compound, any one step of IM being ready to pass through in above-mentioned steps is synthesized, it is possible to
It is not limited to this.
The synthetic method of following IM1 is as follows.
In round-bottomed flask, iodo- 1, the 1'- of the bromo- 4'- of 4- of [1,1'- biphenyl] -4- ylboronic acid of 27.6g, 50.0g is joined
Benzene is dissolved in after Isosorbide-5-Nitrae-dioxanes of 800ml, is put into K2CO3(2M) 210ml and Pd (PPh3)4After 4.8g, return stirring.
Reaction is confirmed using thin-layered chromatography (TLC), and after adding water, reaction was completed.It is extracted using methylcellulose (MC)
Organic layer, and after being filtered under diminished pressure, it is recrystallized to obtain the intermediate compound I M1 of 50.4g (yield 74%).
Following IM2 to IM13 is synthesized using different initial substances by method identical with above-mentioned IM1.
The synthesis of preparation example 2.OP
The synthetic method of following OP1 is as follows.
In round-bottomed flask, by bromo- 9, the 9- dimethyl -9H- fluorenes of the above-mentioned 2- of 15.0g, the aniline of 5.6g, t-BuONa
7.9g、Pd2(dba)3 2.0g、(t-Bu)3P 2.5ml is dissolved in after the toluene of 200ml, return stirring.Utilize thin-layer chromatography
Method (TLC) confirms reaction, and after adding water, reaction was completed.Organic layer is extracted using methylcellulose (MC), and is carried out
After being filtered under diminished pressure, recrystallized to obtain the OP1 of 11.75g (yield 75%).
Following OP2 to OP3 is synthesized using different initial substances by method identical with above-mentioned OP1.
The synthesis of 1. compound 1 of synthesis example
In round-bottomed flask, by OP1, t-BuONa 1.9g, the Pd of the IM 1 of 5.0g, 3.7g2(dba)3 0.5g、(t-
Bu)3P 0.5ml is dissolved in after the toluene of 130ml, return stirring.Reaction is confirmed using thin-layered chromatography (TLC), and is added
After adding water, reaction was completed.Organic layer is extracted using methylcellulose (MC), and after being filtered under diminished pressure, it is pure to carry out column
Change and recrystallizes to obtain the compound 1 of 5.36g (yield 70%).
M/z:589.28 (100.0%), 590.28 (49.1%), 591.28 (11.8%), 592.29 (1.8%)
The synthesis of 2. compound 2 of synthesis example
OP1 is replaced using OP2, by method identical with compound 1, synthesizes compound 2.(yield 68%)
M/z:639.29 (100.0%), 640.30 (53.4%), 641.30 (14.0%), 642.30 (2.4%)
The synthesis of 3. compound 3 of synthesis example
OP1 is replaced using OP3, by method identical with compound 1, synthesizes compound 3.(yield 65%)
M/z:713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)
The synthesis of 4. compound 4 of synthesis example
IM1 and OP1 is replaced using IM2 and OP3, by method identical with compound 1, synthesizes compound 4.(yield
72%)
M/z:713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)
The synthesis of 5. compound 5 of synthesis example
IM1 and OP1 is replaced using IM3 and OP3, by method identical with compound 1, synthesizes compound 5.(yield
65%)
M/z:713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)
The synthesis of 6. compound 6 of synthesis example
IM1 and OP1 is replaced using IM4 and OP3, by method identical with compound 1, synthesizes compound 6.(yield
67%)
M/z:713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)
The synthesis of 7. compound 7 of synthesis example
IM1 and OP1 is replaced using IM5 and OP3, by method identical with compound 1, synthesizes compound 7.(yield
62%)
M/z:713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)
The synthesis of 8. compound 8 of synthesis example
IM1 and OP1 is replaced using IM6 and OP3, by method identical with compound 1, synthesizes compound 8.(yield
63%)
M/z:713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)
The synthesis of 9. compound 9 of synthesis example
IM1 and OP1 is replaced using IM7 and OP3, by method identical with compound 1, synthesizes compound 9.(yield
63%)
M/z:713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)
The synthesis of 10. compound 10 of synthesis example
IM1 and OP1 is replaced using IM8 and OP3, by method identical with compound 1, synthesizes compound 10.(yield
60%)
M/z:713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)
The synthesis of 11. compound 11 of synthesis example
IM1 and OP1 is replaced using IM9 and OP3, by method identical with compound 1, synthesizes compound 11.(yield
56%)
M/z:713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)
The synthesis of 12. compound 12 of synthesis example
IM1 and OP1 is replaced using IM10 and OP3, by method identical with compound 1, synthesizes compound 12.It (receives
Rate 60%)
M/z:713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)
The synthesis of 13. compound 13 of synthesis example
IM1 and OP1 is replaced using IM11 and OP3, by method identical with compound 1, synthesizes compound 13.It (receives
Rate 58%)
M/z:713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)
The synthesis of 14. compound 14 of synthesis example
IM1 and OP1 is replaced using IM12 and OP3, by method identical with compound 1, synthesizes compound 14.It (receives
Rate 60%)
M/z:713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)
The synthesis of 15. compound 15 of synthesis example
IM1 and OP1 is replaced using IM13 and OP3, by method identical with compound 1, synthesizes compound 15.It (receives
Rate 48%)
M/z:713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)
Embodiment 1: the manufacture of organic luminescent device
By distilled water ultrasonic wave toThickness by tin indium oxide (ITO) be applied as the glass substrate of film into
Row washing.If distillation water washing terminates, ultrasonic washing is carried out using isopropanol, acetone, methanol equal solvent, and done
After dry, it is transferred to plasma cleaner, after then cleaning aforesaid substrate 5 minutes using oxygen plasma, in indium oxide
Tinbase plate top utilizes thermal vacuum depositor (thermal evaporator), will as hole injection layerH101 into
Row film, willHATCN be filmed, as hole transporting layer willNPB be filmed, as luminous auxiliary
Layer willCompound 1 be filmed after, as above-mentioned luminescent layer doping 3% BH01:BD01, withIt carries out
Film.It then, will as electron supplying layerET01:Liq (1:1) be filmed after, willLiF,Aluminium (Al) be filmed, and in glove box seal (Encapsulation) device, to be prepared for organic
Luminescent device.
Embodiment 2 is to embodiment 15: the preparation of organic luminescent device
Using method same as Example 1, it is prepared for send out using compound 2 to compound 15 instead of compound 1
The organic luminescent device that light auxiliary layer is filmed.
Comparative example 1 is to comparative example 9
Compound 1 is replaced to be prepared for using following Ref.1 to Ref.9 using method same as Example 1, and respectively
Organic luminescent device.
Experimental example 1: the performance evaluation of organic luminescent device
Apply electricity using 2400 source measuring unit of Keithley (Kiethley 2400source measureme nt unit)
Pressure is measured to inject electronics and hole 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
| Op.V | mA/cm2 | Cd/A | QE (%) | CIEx | CIEy | LT97 | |
| Embodiment 1 | 3.85 | 10 | 7.13 | 6.04 | 0.140 | 0.109 | 115 |
| Embodiment 2 | 3.86 | 10 | 7.15 | 6.00 | 0.140 | 0.110 | 118 |
| Embodiment 3 | 3.91 | 10 | 7.25 | 6.23 | 0.140 | 0.109 | 132 |
| Embodiment 4 | 3.97 | 10 | 7.45 | 6.28 | 0.140 | 0.110 | 153 |
| Embodiment 5 | 3.92 | 10 | 7.40 | 6.25 | 0.141 | 0.110 | 152 |
| Embodiment 6 | 3.91 | 10 | 7.37 | 6.25 | 0.140 | 0.110 | 151 |
| Embodiment 7 | 3.92 | 10 | 7.40 | 6.25 | 0.140 | 0.110 | 152 |
| Embodiment 8 | 3.90 | 10 | 7.40 | 6.20 | 0.140 | 0.109 | 150 |
| Embodiment 9 | 3.90 | 10 | 7.38 | 6.22 | 0.139 | 0.110 | 153 |
| Embodiment 10 | 3.90 | 10 | 7.35 | 6.23 | 0.141 | 0.110 | 150 |
| Embodiment 11 | 3.92 | 10 | 7.35 | 6.25 | 0.140 | 0.110 | 150 |
| Embodiment 12 | 3.90 | 10 | 7.48 | 6.21 | 0.140 | 0.111 | 144 |
| Embodiment 13 | 3.95 | 10 | 7.38 | 6.20 | 0.140 | 0.110 | 153 |
| Embodiment 14 | 3.95 | 10 | 7.42 | 6.25 | 0.140 | 0.110 | 150 |
| Embodiment 15 | 3.95 | 10 | 7.47 | 6.29 | 0.141 | 0.110 | 151 |
| Comparative example 1 | 4.25 | 10 | 6.40 | 5.68 | 0.142 | 0.111 | 70 |
| Comparative example 2 | 4.28 | 10 | 6.94 | 5.76 | 0.143 | 0.110 | 82 |
| Comparative example 3 | 4.05 | 10 | 6.48 | 5.44 | 0.141 | 0.112 | 70 |
| Comparative example 4 | 4.03 | 10 | 6.54 | 5.50 | 0.141 | 0.111 | 75 |
| Comparative example 5 | 4.02 | 10 | 6.90 | 5.35 | 0.141 | 0.110 | 89 |
| Comparative example 6 | 4.05 | 10 | 6.49 | 5.50 | 0.143 | 0.110 | 62 |
| Comparative example 7 | 4.09 | 10 | 6.51 | 5.71 | 0.141 | 0.111 | 67 |
| Comparative example 8 | 4.05 | 10 | 6.88 | 5.60 | 0.141 | 0.110 | 85 |
| Comparative example 9 | 4.09 | 10 | 7.02 | 5.60 | 0.141 | 0.111 | 97 |
As shown in Table 1 above, the embodiment of the present invention is compared with comparative example 1 to comparative example 9, it is seen that driving voltage is low, effect
The result that rate and service life rise.
More specifically, the embodiment of the present invention, 1) compared with comparative example 1 to 3, according to the linearly connected for passing through 4 phenyl
Conjugation expansion, can increase hole flow, 2) compared with comparative example 4 and 5, by the aryl of the other side in the aryl of arylamine
It is not the aryl of linearly connected, is minimised as C10Aryl below, can maintain HOMO, LUMO appropriate and high T1,3) with than
Compared compared with example 6 to 8, by the aryl of linearly connected rather than branch aryl, so that the molecules align on film is become outstanding, can have
There is a faster hole flow, 4) compared with comparative example 9, do not replace heavy hydrogen, high-purity purifying easy to accomplish can induce organic hair
When the compound of the present invention of the long-life of optical device is suitable for organic luminescent device, it is seen that driving voltage is low, efficiency and service life
It substantially improves.
The explanation of aforementioned present invention is for illustrative, and 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 technical idea or essential feature of the invention.Therefore,
It should be understood that various embodiments described above be in all respects it is illustrative, 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 and range and the mode for having altered or deforming as derived from its equivalents for inventing claimed range 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 indicated by following formula 1:
Chemical formula 1
In the chemical formula 1,
Ar1To Ar4It is each independently substituted or unsubstituted C6~C30Aryl or substituted or unsubstituted C5~C30's
Heteroaryl,
Ar5For substituted or unsubstituted C6~C10Aryl,
R、R`、R1And R2It is each independently hydrogen, substituted or unsubstituted C1~C30Alkyl, substituted or unsubstituted C2~C30
Alkenyl, substituted or unsubstituted C6~C30Aryl or substituted or unsubstituted C5~C30Heteroaryl,
L be 0 perhaps 1 to 4 integer m be 0 or integer of 1 to 3.
2. compound according to claim 1, which is characterized in that the Ar5For phenyl or naphthalene.
3. compound according to claim 1, which is characterized in that the compound is indicated by following formula 2:
Chemical formula 2
In the chemical formula 2,
R3For hydrogen, substituted or unsubstituted C1~C30Alkyl or substituted or unsubstituted C2~C30Alkenyl,
The integer that n is 0 or 1 to 5.
4. compound according to claim 3, which is characterized in that the compound is indicated by following formula 3:
Chemical formula 3
In the chemical formula 3,
R3For hydrogen, substituted or unsubstituted C1~C30Alkyl or substituted or unsubstituted C2~C30Alkenyl,
The integer that n is 0 or 1 to 5,
Ar and Ar ' is each independently substituted or unsubstituted C6~C30Aryl,
R6To R8It is each independently hydrogen, substituted or unsubstituted C1~C30Alkyl, substituted or unsubstituted C2~C30Alkene
Base, substituted or unsubstituted C6~C30Aryl or substituted or unsubstituted C5~C30Heteroaryl.
5. compound according to claim 4, which is characterized in that the compound is indicated by following formula 4:
Chemical formula 4
In the chemical formula 4,
R3For hydrogen, substituted or unsubstituted C1~C30Alkyl or substituted or unsubstituted C2~C30Alkenyl,
The integer that n is 0 or 1 to 5,
R4And R5It is each independently hydrogen, substituted or unsubstituted C1~C30Alkyl, substituted or unsubstituted C2~C30Alkene
Base, substituted or unsubstituted C6~C30Aryl or substituted or unsubstituted C5~C30Heteroaryl,
R6To R9It is each independently hydrogen, substituted or unsubstituted C1~C30Alkyl, substituted or unsubstituted C2~C30Alkene
Base, substituted or unsubstituted C6~C30Aryl or substituted or unsubstituted C5~C30Heteroaryl.
6. compound according to claim 1 or 2, which is characterized in that the Ar1To Ar4It is each independently phenyl, naphthalene
Base or phenanthryl.
7. compound according to claim 1, which is characterized in that by-Ar in the chemical formula 11-Ar2-Ar3-Ar4Table
The substituent group shown has more than one meta position or ortho position key.
8. compound according to claim 1, which is characterized in that the compound indicated by the chemical formula 1 is followingization
Close one of object:
9. a kind of organic luminescent device, which is characterized in that include containing claim 1 institute between first electrode and second electrode
The organic matter layer for the compound stated.
10. organic luminescent device according to claim 9, which is characterized in that the organic matter layer is hole injection layer, sky
1 layer or more in cave transfer layer and luminous auxiliary layer.
11. organic luminescent device according to claim 10, which is characterized in that the organic matter layer is the auxiliary layer that shines.
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| CN113493389A (en) * | 2020-04-03 | 2021-10-12 | 株式会社半导体能源研究所 | Arylamine compound, material for hole transport layer and hole injection layer, light-emitting device and device, electronic device, and lighting device |
| WO2022250103A1 (en) * | 2021-05-28 | 2022-12-01 | 出光興産株式会社 | Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device |
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| KR102559469B1 (en) | 2023-07-25 |
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