CN104854089A - Organic electroluminescence compounds and organic electroluminescence device comprising the same - Google Patents

Organic electroluminescence compounds and organic electroluminescence device comprising the same Download PDF

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CN104854089A
CN104854089A CN201380053644.0A CN201380053644A CN104854089A CN 104854089 A CN104854089 A CN 104854089A CN 201380053644 A CN201380053644 A CN 201380053644A CN 104854089 A CN104854089 A CN 104854089A
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substituted
aryl
unsubstituted
alkyl
yuan
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J-H·金
H-J·李
Y-G·金
H-N·申
K-J·李
H-Y·娜
Y－J·曹
H-J·权
B-O·金
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Rohm and Haas Electronic Materials Korea Ltd
Rohm and Haas Electronic Materials LLC
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Abstract

The present invention relates to an organic electroluminescence compound and an organic electroluminescence device containing the same. Using the organic electroluminescence compound according to the present invention, it is possible to manufacture an organic electroluminescence device having long lifespan and high luminous efficiency.

Description

Organic electroluminescent compounds and the Organnic electroluminescent device comprising described compound
Technical field
The present invention relates to organic electroluminescent compounds and the Organnic electroluminescent device comprising described compound.
Background technology
Electroluminescent (EL) device is automatic luminous device, and its advantage is that it provides more wide viewing angle, larger contrast ratio and faster response time compared with LCD.Organic El device develops [Applied Physics journal (Appl.Phys.Lett.) 51 by Eastman Kodak Company (Eastman Kodak) by using little aromatic diamine molecule and aluminium complex at first as the material for the formation of luminescent layer, 913,1987].
The most important factor of the luminous efficiency in decision organic El device is luminescent material.For functional object, electroluminescent material comprises material of main part and dopant material.Typically, the known device with much excellent electroluminescence characters has following structure, and wherein body-dopant has doping agent to form electroluminescence layer.Recently, the exploitation with high-level efficiency and long-life organic El device is needed just urgently.Specifically, consider the electroluminescence characters needed for medium-to-large oled panel, for than conventional electroluminescent material high the exploitation of many material is urgent.
Serve as the solvent in solid phase and the material of main part played a role in transferring energy should have high purity and must have and is adapted to carry out vacuum-deposited molecular weight.In addition, glass transition temp and heat decomposition temperature should be very high to guarantee thermostability, and need high electrochemical stability to realize the long lifetime, and the formation of noncrystal membrane should become simple, and must well but interlayer should not occur move with the adhesive power of the material of other adjacent layers.
Up to now, fluorescent host material is widely used as material of main part.About blue-fluorescence material of main part, in Idemitsu Kosen Co., Ltd., (Idemitsu Kosan) develops 4,4 '-bis-(2,2 '-diphenylacetylene)-1, after 1 '-biphenyl (DPVBi), have studied multiple material and made its commercialization.Although the dinaphthyl anthracene of the blue light material system of known Idemitsu Kosen Co., Ltd. and Kodak (Kodak), four (tertiary butyl) perylene system has been carried out multiple research so far and has been developed the blue-fluorescence material of main part that can provide better feature in a device.
The special permission of korean patent application case discloses No. 10-2011-0002156A, KR, No. 10-2011-0058243A, KR, No. 10-2011-0058245A, KR, No. 10-2011-0058246A, KR, No. 10-2011-0058248A, KR, No. 10-2012-0038402A, KR etc. and discloses multiple anthracene derivant.But, there is no the disclosure using described derivative as the fluorescent host material of luminescent layer.
The present inventor finds that the ad hoc structure of anthracene derivant is applicable to the fluorescent host material of luminescent layer.
Summary of the invention
Technical problem
Target of the present invention is to provide the fluorescent host material that can be used as luminescent layer has the anthracene derivant of the Organnic electroluminescent device of long lifetime and high-luminous-efficiency ad hoc structure with realization.
The solution of problem
In order to realize described object, the invention provides a kind of organic electroluminescent compounds represented by following formula 1:
Wherein
L 1represent singly-bound, substituted or unsubstituted (C6-C30) arylidene or substituted or unsubstituted 5 to 30 yuan of inferior heteroaryls;
Ar 1represent substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C1-C30) alkyl (C6-C30) aryl or substituted or unsubstituted 5 to 30 yuan of heteroaryls;
Ar 2and Ar 3represent hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 5 to 30 yuan of heteroaryls or-NR independently of one another 1r 2;
R 1and R 2represent hydrogen, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted 5 to 30 yuan of heteroaryls independently of one another; Or binding is to form monocycle or many rings, 3 to 30 yuan of alicyclic rings or aromatic ring each other, the carbon atom of described ring can be selected from the heteroatoms displacement of nitrogen, oxygen and sulphur with at least one;
Ring A and ring C represents the aromatic ring represented by following formula 1a independently of one another;
Ring B represents 5 rings represented by following formula 1b;
Y represents-O-,-S-,-N (R 21)-or-C (R 22) (R 23)-; When Y is-S-, L 1it not singly-bound;
R represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted 5 to 30 yuan of heteroaryls;
R 21to R 23represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted 5 to 30 yuan of heteroaryls independently of one another; Or being bonded to adjacent substituents to form monocycle or many rings, 3 to 30 yuan of alicyclic rings or aromatic ring, the carbon atom of described ring can be selected from the heteroatoms displacement of nitrogen, oxygen and sulphur with at least one; At L 1when being arylidene, R 22and R 23be asynchronously aryl, or R 22and R 23binding does not form ring each other; And
A represents 1 or 2; When a is 2, each R is identical or different.
Advantageous effect of the present invention
Use organic electroluminescent compounds according to the present invention as the fluorescent host of luminescent layer, likely manufacture a kind of Organnic electroluminescent device with long lifetime and high-luminous-efficiency.
Embodiment
Hereinafter, will describe the present invention.But, below describe and be intended to explain the present invention, and do not intend to limit the scope of the invention by any way.
The present invention relates to by the organic electroluminescent compounds represented with above formula 1, comprise the electroluminescent organic material of described compound and comprise the Organnic electroluminescent device of described material.
To be described in detail by the compound represented with above formula 1.
In this article, " alkyl " comprises methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl etc., " thiazolinyl " comprises vinyl, 1-propenyl, 2-propenyl, 1-butylene base, crotyl, 3-butenyl, 2-methyl but-2-ene base etc., " alkynyl " comprises ethynyl, 1-proyl, 2-propynyl, ethyl acetylene base, 2-butyne base, 3-butynyl, 1-methylpent-2-alkynyl etc., " cycloalkyl " comprises cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl etc., " 5 to 7 yuan of Heterocyclylalkyls " has at least one to be selected from B, N, O, S, P (=O), the heteroatoms of Si and P, preferably O, S and N and the cycloalkyl of 5 to 7 ring backbone atoms, and comprise tetrahydrofuran (THF), tetramethyleneimine, thiacyclopentane, tetrahydropyrans etc., " (Asia) aryl " is the monocycle or the condensed ring that are derived from aromatic hydrocarbons, and comprises phenyl, xenyl, terphenyl, naphthyl, binaphthylyl, phenyl napthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, phenyl phenanthryl, anthryl, indenyl, triphenylenyl, pyrenyl, naphthacenyl, perylene base, Qu Ji, thick tetraphenyl, fluoranthene base etc., " 3 to 30 yuan of (Asia) heteroaryls " be have at least one, preferably 1 to 4 be selected from the heteroatoms of the group be made up of B, N, O, S, P (=O), Si and P and the aryl of 3 to 30 ring backbone atoms, the condensed ring being monocycle or condensing with at least one phenyl ring, can fractional saturation, can be by making at least one heteroaryl or aryl be bonded to via singly-bound the group that heteroaryl formed, and comprise monocyclic heteroaryl, as furyl, thienyl, pyrryl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl group, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazine base, triazolyl, tetrazyl, furan a word used for translation base, pyridyl, pyrazinyl, pyrimidyl, pyridazinyl etc., with condensed ring type heteroaryl, as benzofuryl, benzothienyl, isobenzofuran-base, dibenzofuran group, dibenzothiophene base, benzimidazolyl-, benzothiazolyl, benzisothiazole base, benzoisoxazole base, benzoxazolyl, pseudoindoyl, indyl, indazolyl, diazosulfide base, quinolyl, isoquinolyl, cinnolines base, quinazolyl, quinoxalinyl, carbazyl, Fei oxazinyl, coffee pyridine base, benzodioxole group etc.In addition, " halogen " comprises F, Cl, Br and I.
Herein, the hydrogen atom that " being substituted " of stating in " substituted or unsubstituted " means in a certain functional group is replaced by another atom or group (i.e. substituting group).With the L in above formula 1 1, Ar 1to Ar 3, R, R 1, R 2and R 21to R 23in the alkyl be substituted, the alkylaryl be substituted, (Asia) aryl be substituted and the substituting group of (Asia) heteroaryl that is substituted are independently of one another for being selected from by least one of the following group formed: deuterium, halogen, (C1-C30) alkyl not being substituted or being optionally substituted by halogen, (C1-C30) alkoxyl group, (C6-C30) aryl, 3 to the 30 yuan of heteroaryls not being substituted or being replaced by (C6-C30) aryl, (C3-C30) cycloalkyl, 5 to 7 yuan of Heterocyclylalkyls, three (C1-C30) alkyl tin groups, alkyl silane groups, three (C6-C30) aryl-silane base, two (C1-C30) alkyl (C6-C30) aryl-silane base, (C1-C30) alkyl two (C6-C30) aryl-silane base, (C2-C30) thiazolinyl, (C2-C30) alkynyl, cyano group, carbazyl, two (C1-C30) alkylamino, two (C6-C30) arylamino not being substituted or being replaced by (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) arylamino, two (C6-C30) aryl boron carbonyl, two (C1-C30) boron alkyl carbonyl, (C1-C30) alkyl (C6-C30) aryl boron carbonyl, (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro and hydroxyl, and preferably independently of one another for being selected from by least one of the following group formed: deuterium, halogen, (C1-C6) alkyl, (C1-C6) alkoxyl group, (C6-C21) aryl, (C1-C6) alkyl (C6-C21) aryl, 5 to 21 yuan of heteroaryls, (C3-C21) cycloalkyl, three (C6-C12) aryl-silane base, cyano group, two (C6-C12) arylamino not being substituted or being replaced by (C1-C6) alkyl.
In formula 1, part preferably be selected from the group be made up of following structure:
Wherein Y, R and a defined in 1.
In formula 1, L 1represent singly-bound, substituted or unsubstituted (C6-C30) arylidene or substituted or unsubstituted 5 to 30 yuan of inferior heteroaryls, preferably represent singly-bound, substituted or unsubstituted (C6-C21) arylidene or substituted or unsubstituted 5 to 21 yuan of inferior heteroaryls, and more preferably represent singly-bound, be not substituted or (C6-C21) arylidene that replaced by (C1-C6) alkyl or (C6-C21) aryl or 5 to the 21 yuan of inferior heteroaryls not being substituted or being replaced by (C6-C21) aryl.
Ar 1represent substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C1-C30) alkyl (C6-C30) aryl or substituted or unsubstituted 5 to 30 yuan of heteroaryls, preferably represent substituted or unsubstituted (C6-C21) aryl, substituted or unsubstituted (C1-C6) alkyl (C6-C21) aryl or substituted or unsubstituted 5 to 21 yuan of heteroaryls, and more preferably represent and not to be substituted or by deuterium, halogen, (C1-C6) alkyl, (C1-C6) alkoxyl group, (C6-C21) aryl, 5 to 21 yuan of heteroaryls, (C3-C21) cycloalkyl, three (C6-C12) aryl-silane base, (C6-C21) aryl that cyano group or two (C6-C12) arylamino replace, (C1-C6) alkyl (C6-C21) aryl not being substituted or being replaced by (C6-C21) aryl, or 5 to the 21 yuan of heteroaryls not being substituted or being replaced by (C6-C21) aryl.
Ar 2and Ar 3represent hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 5 to 30 yuan of heteroaryls or-NR independently of one another 1r 2, preferably represent hydrogen, substituted or unsubstituted (C6-C21) aryl, substituted or unsubstituted 5 to 21 yuan of heteroaryls or-NR independently of one another 1r 2, and (C6-C21) aryl, unsubstituted 5 to 21 yuan of heteroaryls or the-NR that more preferably represent hydrogen independently of one another, be not substituted or replaced by (C1-C6) alkyl 1r 2.
R 1and R 2represent hydrogen, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted 5 to 30 yuan of heteroaryls independently of one another; Or each other binding to form monocycle or many rings, 3 to 30 yuan of alicyclic rings or aromatic ring, the carbon atom of described ring can be selected from the heteroatoms displacement of nitrogen, oxygen and sulphur with at least one, preferably represent hydrogen or substituted or unsubstituted (C6-C21) aryl independently of one another, and (C6-C21) aryl more preferably representing hydrogen independently of one another or be not substituted or replaced by (C1-C6) alkyl.
Y represents-O-,-S-,-N (R 21)-or-C (R 22) (R 23)-; When Y is-S-, L 1it not singly-bound.
R represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted 5 to 30 yuan of heteroaryls, preferably represent hydrogen or substituted or unsubstituted (C6-C21) aryl, and more preferably represent hydrogen or unsubstituted (C6-C21) aryl.
R 21to R 23represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted 5 to 30 yuan of heteroaryls independently of one another; Or being bonded to adjacent substituents to form monocycle or many rings, 3 to 30 yuan of alicyclic rings or aromatic ring, the carbon atom of described ring can be selected from the heteroatoms displacement of nitrogen, oxygen and sulphur with at least one; At L 1when being arylidene, R 22and R 23be asynchronously aryl, or R 22and R 23binding does not form ring each other, preferably represents substituted or unsubstituted (C1-C6) alkyl or substituted or unsubstituted (C6-C21) aryl independently of one another; At L 1when being arylidene, R 22and R 23be asynchronously aryl, or R 22and R 23binding does not form ring each other, and more preferably represents unsubstituted (C1-C6) alkyl or unsubstituted (C6-C21) aryl independently of one another; At L 1when being arylidene, R 22and R 23be asynchronously aryl, or R 22and R 23binding does not form ring each other.
According to one embodiment of present invention, in formula 1, L 1represent singly-bound, substituted or unsubstituted (C6-C21) arylidene or substituted or unsubstituted 5 to 21 yuan of inferior heteroaryls; Ar 1represent substituted or unsubstituted (C6-C21) aryl, substituted or unsubstituted (C1-C6) alkyl (C6-C21) aryl or substituted or unsubstituted 5 to 21 yuan of heteroaryls; Ar 2and Ar 3represent hydrogen, substituted or unsubstituted (C6-C21) aryl, substituted or unsubstituted 5 to 21 yuan of heteroaryls or-NR independently of one another 1r 2; R 1and R 2represent hydrogen or substituted or unsubstituted (C6-C21) aryl independently of one another; Y represents-O-,-S-,-N (R 21)-or-C (R 22) (R 23)-; When Y is-S-, L1 is not singly-bound; R represents hydrogen or substituted or unsubstituted (C6-C21) aryl; And R 21to R 23represent substituted or unsubstituted (C1-C6) alkyl or substituted or unsubstituted (C6-C21) aryl independently of one another; At L 1when being arylidene, R 22and R 23be asynchronously aryl, or R 22and R 23binding does not form ring each other.
According to another embodiment of the present invention, in formula 1, L 1represent singly-bound; (C6-C21) arylidene not being substituted or being replaced by (C1-C6) alkyl or (C6-C21) aryl; Or 5 to the 21 yuan of inferior heteroaryls not being substituted or being replaced by (C6-C21) aryl; Ar 1represent (C6-C21) aryl not being substituted or being replaced by deuterium, halogen, (C1-C6) alkyl, (C1-C6) alkoxyl group, (C6-C21) aryl, 5 to 21 yuan of inferior heteroaryls, (C3-C21) cycloalkyl, three (C6-C12) aryl-silane base, cyano group or two (C6-C12) arylaminos; (C1-C6) alkyl (C6-C21) aryl not being substituted or being replaced by (C6-C21) aryl; Or 5 to the 21 yuan of heteroaryls not being substituted or being replaced by (C6-C21) aryl; Ar 2and Ar 3represent hydrogen independently of one another; (C6-C21) aryl not being substituted or being replaced by (C1-C6) alkyl; Unsubstituted 5 to 21 yuan of heteroaryls; Or-NR 1r 2; R 1and R 2(C6-C21) aryl representing hydrogen independently of one another or be not substituted or replaced by (C1-C6) alkyl; Y represents-O-,-S-,-N (R 21)-or-C (R 22) (R 23)-; When Y is-S-, L 1it not singly-bound; R represents hydrogen or unsubstituted (C6-C21) aryl; And R 21to R 23represent unsubstituted (C1-C6) alkyl or unsubstituted (C6-C21) aryl independently of one another; At L 1when being arylidene, R 22and R 23be asynchronously aryl, or R 22and R 23binding does not form ring each other.
Representative formula 1 compound comprises following compound, but is not limited thereto:
Organic electroluminescent compounds of the present invention is prepared by the synthetic method that those skilled in the art is known.Such as, it can be prepared according to following reaction scheme 1 or 2.
[reaction scheme 1]
[reaction scheme 2]
Wherein Ar 1, Ar 2, Ar 3, L 1, R, a, ring A, ring B and ring C as with in above formula 1 define, and Hal represents halogen.
In addition, the invention provides the electroluminescent organic material of the organic electroluminescent compounds of contained 1, and comprise the Organnic electroluminescent device of described material.
Described material can comprise independent according to organic electroluminescent compounds of the present invention, maybe can be additionally contained in the conventional material comprised in electroluminescent organic material.
Described Organnic electroluminescent device comprises the first electrode; Second electrode; And at least one organic layer between first and second electrode described.Described organic layer can comprise at least one according to formula 1 compound of the present invention.
One in described first and second electrodes is anode, and another one is negative electrode.Described organic layer comprises luminescent layer, and at least one is selected from the layer of the group be made up of hole injection layer, hole transmission layer, electron transfer layer, electron injecting layer, interlayer, hole blocking layer and electronic barrier layer.
In addition, described organic layer comprises luminescent layer, and the organic electroluminescent compounds of described formula 1 can be used as the material of main part in described luminescent layer.
In addition, described luminescent layer can comprise fluorescent dopants material and material of main part of the present invention.
Fluorescent dopants is can by the compound of single excitonic luminescence.Fluorescent dopants is preferably selected from the compound based on the compound of amine, aromatics, inner complex (as three (oxine) aluminium misfit thing), coumarin derivatives, tetraphenylbutadiene derivative, bisstyryl arylene derivatives, oxadiazole derivative etc. according to required glow color.Styrylamine compounds, styryl diamine compound, novel arylamine compound and aryl diamine compound are preferred, and wherein fused polycycle sulfonamide derivatives even more preferably.These fluorescent dopants can use separately or with both or both above array configurations.
When described fused polycycle sulfonamide derivatives is included as the fluorescent dopants of Organnic electroluminescent device according to the present invention, the compound represented by following formula 2 can be used.
Wherein
Ar 21represent substituted or unsubstituted (C6-C50) aryl or styryl; L represents singly-bound, substituted or unsubstituted (C6-C30) arylidene or substituted or unsubstituted 3 to 30 yuan of inferior heteroaryls; Ar 22and Ar 23represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted 3 to 30 yuan of heteroaryls independently of one another; Or being bonded to adjacent substituents to form monocycle or many rings, 3 to 30 yuan of alicyclic rings or aromatic ring, the carbon atom of described ring can be selected from the heteroatoms displacement of nitrogen, oxygen and sulphur with at least one; N represents 1 or 2, when n is 2, respectively identical or different.
Ar 21preferred aryl groups be substituted or unsubstituted phenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted base in the wrong and substituted or unsubstituted benzo fluorenyl etc.
Representative formula 2 compound comprises following compound, but is not limited thereto:
Except the organic electroluminescent compounds represented by formula 1, at least one can be comprised further according to Organnic electroluminescent device of the present invention and be selected from by the compound of the group formed based on the compound of arylamines and the compound of styrene-based base arylamines.
In Organnic electroluminescent device according to the present invention, described organic layer can comprise at least one further and be selected from by the metal of the following group formed: the organo-metallic of the 1st race's metal of periodictable, group II metal, the 4th row transition metals, the 5th row transition metals, lanthanon and d-transition element, or comprises at least one misfit compounds of described metal.Described organic layer can comprise luminescent layer and charge generation layer further.
In addition, described organic layer can form Organnic electroluminescent device, described device is by comprising at least one organic luminous layer and transmitting white further, and described luminescent layer also comprises blue light electroluminescent compounds, ruddiness electroluminescent compounds or green glow electroluminescent compounds except described organic electroluminescent compounds.
According to the present invention, at least one layer (hereinafter, " upper layer ") can be preferably located on the internal surface of one or two electrode, is selected from chalcogenide layer, metal halide and metal oxide layer.Specifically, chalkogenide (the comprising oxide compound) layer of silicon or aluminium is preferably located on the anode surface in electroluminescent middle layer, and metal halide or metal oxide are preferably located on the cathode surface in electroluminescent middle layer.This type of upper layer provides operational stability for Organnic electroluminescent device.Preferably, described chalkogenide comprises SiO x(1≤X≤2), AlO x(1≤X≤1.5), SiON, SiAlON etc.; Described metal halide comprises LiF, MgF 2, CaF 2, rare earth metal fluorochemical etc.; And described metal oxide comprises Cs 2o, Li 2o, MgO, SrO, BaO, CaO etc.
In Organnic electroluminescent device according to the present invention, the mixing region of the mixing region of electric transmission compound and reductibility doping agent or hole transport compound and oxidisability doping agent can be preferably located in pair of electrodes at least one on the surface.In this case, electric transmission compound is reduced to negatively charged ion, and therefore become easier from mixing region spray and transmission electronic to electroluminescent medium.In addition, hole transport compound is oxidized to positively charged ion, and therefore become easier from mixing region spray and transporting holes to electroluminescent medium.Preferably, oxidisability doping agent comprises various Lewis acid (Lewis acid) and acceptor compound; And originality doping agent comprises basic metal, alkali metal compound, alkaline-earth metal, rare earth metal and its mixture.Reductibility dopant layer can be used as charge generation layer has two or more electroluminescence layers and transmitting white el light emitting device with preparation.
In order to form the every one deck according to Organnic electroluminescent device of the present invention, dry type film can be used, as vacuum-evaporation, sputtering, plasma body and ion plating method; Or wet type film, as spin coating, dip-coating and flow coating processes.
When using wet type film, film can by being formed the material dissolves or be diffused in any suitable solvent forming every one deck, and described solvent is ethanol, chloroform, tetrahydrofuran (THF), diox etc. such as.Solvent can be that the material forming every one deck can dissolve or be spread in wherein and there is not any solvent of film forming ability problem.
Hereinafter, the preparation method of described organic electroluminescent compounds, described compound and the characteristics of luminescence of described device is explained in detail with reference to following instance.
example 1: prepare compound H-1
At mixing cpd A 4.5g (0.016mol), 9-bromo-10-phenylanthracene 6.3g (0.019mol), CuI 1.5g (0.008mol), K 3pO 4after 10.4g (0.049mol), quadrol (EDA) 1.1mL (O.016mol) and toluene 150mL, mixture is heated to 120 DEG C, and stirs 12 hours.After the reaction was completed, described mixture distilled water wash, with ethyl acetate (EA) extraction, organic layer MgSO 4drying, solvent uses rotary evaporator to remove, and resultant product uses tower to be separated to obtain compound H-1 4.0g (46.5%).
Fusing point 307 DEG C, UV 268nm (in methylene dichloride (MC)), PL 420nm (in MC), molecular weight 535.68
example 2: prepare compound H-128
To toluene 150mL, ethanol 50mL and H 2compd B 7g (15.9mmol), 10-phenylanthracene-9-ylboronic acid 2.3g (8.6mmol), Pd (PPh is added in the mixed solvent of O 50mL 3) 4568mg (0.5mmol) and Na 2cO 3after 5.1g (47.91mmol), mixture stirs 4 hours at 120 DEG C.After the reaction was completed, described mixture cool to room temperature lentamente, adds water, and extracts with EA.Then, organic layer Na 2sO 4drying, and resultant product concentrates, and use tower to be separated to obtain compound H-128 4.9g (50%).
Fusing point 324 DEG C, UV 258nm (in MC), PL 431nm (in MC), molecular weight 611.26
example 3: prepare compound H-174
Compound H-174 3.2g (28.5%) uses Compound C 8g (18.6mmol) and 10-phenylanthracene-9-ylboronic acid 5.1g (22.4mmol) to prepare in the mode identical with the synthetic method of compound H-128.
Fusing point 272 DEG C, UV 305nm (in MC), PL 412nm (in MC), molecular weight 601.19
Example 4: prepare compound H-175
Compound H-175 6g (70%) uses Compound D 6g (15mmol) and 10-phenylanthracene-9-ylboronic acid 4.45g (16mmol) to prepare in the mode identical with the synthetic method of compound H-128.
Fusing point 313 DEG C, UV 352nm (in toluene), PL 420nm (in toluene), molecular weight 585.21
example 5: prepare compound H-179
Compound H-179 3.7g (54%) uses compd E 5.1g (10.1mmol) and 10-phenylanthracene-9-ylboronic acid 2.9g (10.6mmol) to prepare in the mode identical with the synthetic method of compound H-128.
Fusing point 318 DEG C, UV 296nm (in MC), PL 419nm (in MC), molecular weight 677.22
device example 1: use and manufacture OLED device according to organic electroluminescent compounds of the present invention
Use and manufacture OLED device according to luminescent material of the present invention.For Organic Light Emitting Diode (OLED) device (SCP (Samsung Corning), Republic of Korea (Republic of Korea)) transparency electrode tin indium oxide (ITO) film (15 Ω/sq) on a glass substrate sequentially carry out ultrasonic washing with trieline, acetone, ethanol and distilled water, and to be stored in subsequently in Virahol.Then, ITO substrate is arranged in the substrate holder of vacuum phase deposition equipment.By 4,4 ', 4 "-three (N, N-(2-naphthyl)-phenyl amino) triphenylamine is incorporated in the unit of described vacuum phase deposition equipment, and subsequently by the pressure-controlling in the chamber of described equipment 10 -6holder.After this, electric current is applied to described unit to evaporate the material of above introducing, on ITO substrate, forms the hole injection layer that thickness is 60nm thus.Then, by N, N '-bis-(Alpha-Naphthyl)-N, N '-phenylbenzene-4,4 '-diamines is incorporated in another unit of described vacuum phase deposition equipment, and makes it evaporate by applying electric current to described unit, forms the hole transmission layer that thickness is 20nm thus on hole injection layer.After this, compound H-128 according to the present invention is incorporated in a unit of vacuum phase deposition equipment as material of main part, and Compound D-9 is incorporated in another unit as doping agent.Described bi-material is with different ratio evaporation and with the doping of the total amount 3wt% based on main body and doping agent deposition to form the luminescent layer that thickness is 30nm on hole transmission layer.Subsequently, three (oxine)-aluminium (III) are incorporated in a unit to form the electron transfer layer that thickness is 30nm on luminescent layer.Thereafter, on the electron transport layer deposit thickness be the quinoline lithium of 2nm as after electron injecting layer, be the A1 negative electrode of 150nm by another vacuum phase deposition equipment deposit thickness on electron injecting layer.Therefore, OLED device is manufactured.All material for the manufacture of OLED device all passes through before the use 10 -6the lower vacuum-sublimation of holder and purifying.
Manufactured OLED device display brightness is 650cd/m 2and current density is 22.4mA/cm 2blue emission.
device example 2: use and manufacture OLED device according to organic electroluminescent compounds of the present invention
OLED device is manufactured, except using compound H-175 as main body and using Compound D-99 as the doping agent of luminescent material in the mode identical with device example 1.
Manufactured OLED device display brightness is 1250cd/m 2and current density is 19.8mA/cm 2blue emission.
device example 3: use and manufacture OLED device according to organic electroluminescent compounds of the present invention
OLED device is manufactured, except using compound H-179 as main body and using Compound D-55 as the doping agent of luminescent material in the mode identical with device example 1.
Manufactured OLED device display brightness is 660cd/m 2and current density is 20.0mA/cm 2blue emission.
device example 4: use and manufacture OLED device according to organic electroluminescent compounds of the present invention
OLED device is manufactured, except using compound H-174 as main body and using Compound D-56 as the doping agent of luminescent material in the mode identical with device example 1.
Manufactured OLED device display brightness is 605cd/m 2and current density is 17.3mA/cm 2blue emission.
Confirm, be used as the fluorescent host of luminescent layer according to organic electroluminescent compounds of the present invention, and be effective to blue emission.

Claims (7)

1. the organic electroluminescent compounds represented by following formula 1,
Wherein
L 1represent singly-bound, substituted or unsubstituted (C6-C30) arylidene or substituted or unsubstituted 5 to 30 yuan of inferior heteroaryls;
Ar 1represent substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C1-C30) alkyl (C6-C30) aryl or substituted or unsubstituted 5 to 30 yuan of heteroaryls;
Ar 2and Ar 3represent hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 5 to 30 yuan of heteroaryls or-NR independently of one another 1r 2;
R 1and R 2represent hydrogen, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted 5 to 30 yuan of heteroaryls independently of one another; Or binding is to form monocycle or many rings, 3 to 30 yuan of alicyclic rings or aromatic ring each other, the carbon atom of described ring can be selected from the heteroatoms displacement of nitrogen, oxygen and sulphur with at least one;
Ring A and ring C represents the aromatic ring represented by following formula 1a independently of one another;
Ring B represents 5 rings represented by following formula 1b;
Y represents-O-,-S-,-N (R 21)-or-C (R 22) (R 23)-; When Y is-S-, L 1it not singly-bound;
R represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted 5 to 30 yuan of heteroaryls;
R 21to R 23represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted 5 to 30 yuan of heteroaryls independently of one another; Or being bonded to adjacent substituents to form monocycle or many rings, 3 to 30 yuan of alicyclic rings or aromatic ring, the carbon atom of described ring can be selected from the heteroatoms displacement of nitrogen, oxygen and sulphur with at least one; At L 1when being arylidene, R 22and R 23be asynchronously aryl, or R 22and R 23binding does not form ring each other; And
A represents 1 or 2; When a is 2, each R is identical or different.
2. organic electroluminescent compounds according to claim 1, wherein L 1, Ar 1to Ar 3, R, R 1, R 2and R 21to R 23in described in the alkyl that is substituted, the described alkylaryl be substituted, the substituting group of described (Asia) aryl that is substituted and described (Asia) heteroaryl be substituted is independently of one another for being selected from by least one of the following group formed: deuterium, halogen, (C1-C30) alkyl not being substituted or being optionally substituted by halogen, (C1-C30) alkoxyl group, (C6-C30) aryl, 3 to the 30 yuan of heteroaryls not being substituted or being replaced by (C6-C30) aryl, (C3-C30) cycloalkyl, 5 to 7 yuan of Heterocyclylalkyls, three (C1-C30) alkyl tin groups, alkyl silane groups, three (C6-C30) aryl-silane base, two (C1-C30) alkyl (C6-C30) aryl-silane base, (C1-C30) alkyl two (C6-C30) aryl-silane base, (C2-C30) thiazolinyl, (C2-C30) alkynyl, cyano group, carbazyl, two (C1-C30) alkylamino, two (C6-C30) arylamino not being substituted or being replaced by (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) arylamino, two (C6-C30) aryl boron carbonyl, two (C1-C30) boron alkyl carbonyl, (C1-C30) alkyl (C6-C30) aryl boron carbonyl, (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro and hydroxyl.
3. organic electroluminescent compounds according to claim 1, wherein part be selected from the group be made up of following structure:
Wherein Y, R and a are as defined in claim 1.
4. organic electroluminescent compounds according to claim 1, wherein L 1represent singly-bound, substituted or unsubstituted (C6-C21) arylidene or substituted or unsubstituted 5 to 21 yuan of inferior heteroaryls;
Ar 1represent substituted or unsubstituted (C6-C21) aryl, substituted or unsubstituted (C1-C6) alkyl (C6-C21) aryl or substituted or unsubstituted 5 to 21 yuan of heteroaryls;
Ar 2and Ar 3represent hydrogen, substituted or unsubstituted (C6-C21) aryl, substituted or unsubstituted 5 to 21 yuan of heteroaryls or-NR independently of one another 1r 2;
R 1and R 2represent hydrogen or substituted or unsubstituted (C6-C21) aryl independently of one another;
Y represents-O-,-S-,-N (R 21)-or-C (R 22) (R 23)-; When Y is-S-, L 1it not singly-bound;
R represents hydrogen or substituted or unsubstituted (C6-C21) aryl; And
R 21to R 23represent substituted or unsubstituted (C1-C6) alkyl or substituted or unsubstituted (C6-C21) aryl independently of one another; At L 1when being arylidene, R 22and R 23be asynchronously aryl, or R 22and R 23binding does not form ring each other.
5. organic electroluminescent compounds according to claim 1, wherein L 1represent singly-bound; (C6-C21) arylidene not being substituted or being replaced by (C1-C6) alkyl or (C6-C21) aryl; Or 5 to the 21 yuan of inferior heteroaryls not being substituted or being replaced by (C6-C21) aryl;
Ar 1represent (C6-C21) aryl not being substituted or being replaced by deuterium, halogen, (C1-C6) alkyl, (C1-C6) alkoxyl group, (C6-C21) aryl, 5 to 21 yuan of inferior heteroaryls, (C3-C21) cycloalkyl, three (C6-C12) aryl-silane base, cyano group or two (C6-C12) arylaminos; (C1-C6) alkyl (C6-C21) aryl not being substituted or being replaced by (C6-C21) aryl; Or 5 to the 21 yuan of heteroaryls not being substituted or being replaced by (C6-C21) aryl;
Ar 2and Ar 3represent hydrogen independently of one another; (C6-C21) aryl not being substituted or being replaced by (C1-C6) alkyl; Unsubstituted 5 to 21 yuan of heteroaryls; Or-NR 1r 2;
R 1and R 2(C6-C21) aryl representing hydrogen independently of one another or be not substituted or replaced by (C1-C6) alkyl;
Y represents-O-,-S-,-N (R 21)-or-C (R 22) (R 23)-; When Y is-S-, L 1it not singly-bound;
R represents hydrogen or unsubstituted (C6-C21) aryl; And
R 21to R 23represent unsubstituted (C1-C6) alkyl or unsubstituted (C6-C21) aryl independently of one another; At L 1when being arylidene, R 22and R 23be asynchronously aryl, or R 22and R 23binding does not form ring each other.
6. organic electroluminescent compounds according to claim 1, the wherein said compound represented by formula 1 is selected from by the following group formed:
7. an Organnic electroluminescent device, it comprises organic electroluminescent compounds according to claim 1.
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