CN105359292A - A combination of a dopant compound and a host compound and an organic electroluminescent device comprising the same - Google Patents

A combination of a dopant compound and a host compound and an organic electroluminescent device comprising the same Download PDF

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CN105359292A
CN105359292A CN201480037637.6A CN201480037637A CN105359292A CN 105359292 A CN105359292 A CN 105359292A CN 201480037637 A CN201480037637 A CN 201480037637A CN 105359292 A CN105359292 A CN 105359292A
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substituted
aryl
unsubstituted
alkyl
yuan
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Y-G·金
H-J·李
J-H·金
J-H·全
C-S·金
Y－J·曹
K-J·李
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Rohm and Haas Electronic Materials Korea Ltd
Rohm and Haas Electronic Materials LLC
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    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • 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
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • 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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Abstract

The present invention relates to a specific combination of a dopant compound comprising an amino-pyrene and a host compound comprising a di-aryl subsituted anthracene, and an organic electroluminescent device comprising the same. The organic electroluminescent device of the present invention provides the advantages of remarkable luminous efficiency, excellent color purity, low driving voltage, and good operational lifespan.

Description

The combination of dopant compound and host compound and comprise the Organnic electroluminescent device of described combination
Technical field
The present invention relates to the combination of dopant compound and host compound, and comprise the Organnic electroluminescent device of described combination.
Background technology
El light emitting device (ELdevice) is a kind of selfluminous device, and its advantage had there are provided wider visual angle, higher contrast ratio and response time faster.Eastman Kodak Co (EastmanKodak) is by using aromatic diamine Small molecular and aluminium complex as the material forming luminescent layer, develop a kind of organic el device [" applied physics bulletin " (Appl.Phys.Lett.) 51 at first, 913,1987].
Organic el device can reduce production cost and material cost, and its advantage had is to provide wider visual angle, higher contrast ratio compared to liquid-crystal apparatus (LCD), and response time faster.Organic el device has developed into significantly has the efficiency of more than 80 times and the useful life of more than 100 times when it occurs at first.
In addition, organic el device is conducive to display and widens, and therefore display is widened and developed rapidly, such as, occurred the organic el device panel of 40 inches.Because display is widened, therefore wish that device has longer useful life and the luminous efficiency of improvement.
In order to improve the useful life of organic el device, need to prevent at device duration of work because produced Joule heat causes material crystalline.Therefore, exploitation is needed to have remarkable electron injection and the organic compound of mobility and high electrochemical stability.
The most important factor of the luminous efficiency of decision organic el device is luminescent material.Described luminescent material is classified as the fluorescent material of the exciton using singlet; And use the phosphor material of triplet state exciton.Generally speaking, use the organic el device of phosphor material to have short useful life, and therefore up to now fluorescent material be widely used.
In addition, main body/dopant system can be used as luminescent material.When only a kind of material is as luminescent material in use, because the emission wavelength that the interaction between molecule is maximum is transformed into longer wavelength, and there occurs problem due to photoemissive attenuation effect, such as colorimetric purity diminishes or unit efficiency declines.Main body/dopant system is conducive to increasing colorimetric purity, luminous efficiency owing to energy transferring, and stability.
About blue-fluorescence material of main part, in Idemitsu Kosen Co., Ltd., (IdemitsuKosan) develops 4,4 '-bis-(2,2 '-diphenylethyllene)-1, after 1 '-biphenyl (DPVBi), work out and the many materials of commercialization.Although the blue material system of Idemitsu Kosen Co., Ltd. and the dinaphthyl anthracene of Kodak, four (tert-butyl group) perylene system is known, has carried out much research up to now and has developed the blue-fluorescence material of main part that can provide better device characteristic.
With regard to fluorescent dopants, compound can be selected for required glow color, such as based on the compound of amine, aromatic compounds, chelate if three (oxine) aluminium complex, coumarin derivative, tetraphenylbutadiene derivative, double styrene arlydene (bisstyrylarylene) derivative Yi are Ji oxadiazole derivative.
Meanwhile, when apply comprise Traditional dopant immunomodulator compounds and host compound luminescent material to organic el device time, in luminous efficiency, power efficiency, work useful life etc., show result unsatisfactory.Especially be difficult to obtain the blue light-emitting with feature in excellent useful life.
Summary of the invention
Technical problem
The first object of the present invention is inserted in organic el device between anode on substrate and negative electrode for providing a kind of wherein organic layer, and wherein said organic layer comprises the luminescent layer of the combination comprising one or more dopant compound and one or more host compounds.The second object of the present invention has high-luminous-efficiency, excellent colorimetric purity, low driving voltage and the organic el device in good work useful life for providing a kind of.
The solution of problem
To achieve these goals, the invention provides the combination of one or more host compounds represented by following formula 1 and one or more dopant compound represented by following formula 2, and comprise the organic el device of described combination:
Wherein
R 1to R 18(C1-C30) alkyl represent hydrogen, deuterium, halogen independently of one another, being substituted or being unsubstituted, (C3-C30) cycloalkyl being substituted or being unsubstituted, (C1-C30) alkoxyl being substituted or being unsubstituted, (C6-C30) aryl being substituted or being unsubstituted or (3 yuan to the 30 yuan) the heteroaryl ,-SiR that are substituted or are unsubstituted 31r 32r 33, cyano group or hydroxyl; Or R 1to R 5, and R 14to R 18be connected to one or more adjacent substituents with form monocycle or many rings, (3 to the 30 yuan) alicyclic ring that is substituted or is unsubstituted or aromatic ring, the carbon atom of wherein said ring can form spirane structure, and one or more carbon atoms of described ring can be selected from the hetero-atom displacement of nitrogen, oxygen and sulphur through at least one;
R 31to R 33(C1-C30) alkyl represent hydrogen, deuterium, halogen independently of one another, being substituted or being unsubstituted, (C6-C30) aryl being substituted or being unsubstituted, or (3 to the 30 yuan) heteroaryl being substituted or being unsubstituted;
Ar 1and Ar 2(C6-C30) aryl represent hydrogen, deuterium independently of one another, being substituted or being unsubstituted, or (3 to the 30 yuan) heteroaryl being substituted or being unsubstituted; Or be connected to one or more adjacent substituents with form monocycle or many rings, (3 to the 30 yuan) alicyclic ring that is substituted or is unsubstituted or aromatic ring, the carbon atom of wherein said ring can form spirane structure, and one or more carbon atoms of described ring can be selected from the hetero-atom displacement of nitrogen, oxygen and sulphur through at least one; Wherein Ar 1and Ar 2be asynchronously hydrogen; And
Described heteroaryl contains the hetero-atom that at least one is selected from B, N, O, S, P (=O), Si and P;
Wherein
Ar 3represent the pyrene being substituted or being unsubstituted;
(C6-C30) arlydene that L represents singly-bound, is substituted or is unsubstituted, or (3 to the 30 yuan) inferior heteroaryl being substituted or being unsubstituted;
Ar 4and Ar 5represent (C6-C30) aryl being substituted or being unsubstituted independently of one another, or (3 to the 30 yuan) heteroaryl being substituted or being unsubstituted; Or Ar 4and Ar 5be connected with nitrogen-atoms with form monocycle or many rings, (3 to the 30 yuan) alicyclic ring that is substituted or is unsubstituted or aromatic ring, one or more carbon atoms of wherein said ring can be selected from the hetero-atom displacement of nitrogen, oxygen and sulphur through at least one; And
N represents the integer of 1 to 3; Wherein n is 2 or is greater than 2, each identical or different.
The beneficial effect of invention
By comprising the particular combination according to dopant compound of the present invention and host compound, likely providing and there is high-luminous-efficiency, excellent colorimetric purity, low driving voltage and the organic el device in good work useful life.
Embodiment
The present invention will be described in detail below.But below describing is for explaining the present invention, instead of in order to limit the scope of the invention in any way.
The present invention relates to the Organnic electroluminescent device of the combination of one or more host compounds comprising and represented by formula 1 and one or more dopant compound represented by formula 2.
The compound represented by above formula 1 and above formula 2 will be described in detail.
In this article, " alkyl " comprises methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, isobutyl group, the tert-butyl group etc.; " thiazolinyl " comprises vinyl, 1-acrylic, 2-acrylic, 1-cyclobutenyl, 2-cyclobutenyl, 3-cyclobutenyl, 2-methyl-2-butene base etc.; " alkynyl " comprises acetenyl, 1-propinyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-valerylene base etc.; " cycloalkyl " comprises cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl etc.; " 5 to 7 yuan of Heterocyclylalkyls " has to be selected from B, N, O, S, P (=O), Si and P, preferably at least one hetero-atom of O, S and N, and 5 to 7 ring skeletal atoms, and comprise the cycloalkyl of oxolane, pyrrolidines, tetrahydrochysene thiophene phenol (Thiolan), oxinane etc." aryl (arlydene) " is monocycle derived from aromatic hydrocarbons or condensed ring, and comprise phenyl, xenyl, terphenyl, naphthyl, binaphthyl (binaphtyl), phenyl napthyl (phenylnaphtyl), naphthylphenyl (naphtylphenyl), fluorenyl, phenylfluorenyl (phenylfluorenyl), benzo fluorenyl (benzofluorenyl), dibenzo fluorenyl, phenanthryl, phenyl phenanthryl, anthryl, indenyl, indanyl, benzo [9, 10] phenanthryl (triphenylenyl), pyrenyl, aphthacene base (tetracenyl), perylene base (perylenyl), Qu Ji (chrysenyl), naphtho-naphthyl (naphthacenyl), fluoranthene base (fluoranthenyl) etc., " 3 to 30 yuan of assorted (Asia) aryl " is the aryl with at least one hetero-atom (preferably 1 to 4 hetero-atoms) and 3-30 ring skeletal atom, and described hetero-atom is selected from the group be made up of B, N, O, S, P (=O), Si and P, the condensed ring that described assorted (Asia) aryl is monocycle or condenses with at least one phenyl ring, described assorted (Asia) aryl can be fractional saturation, described assorted (Asia) aryl can be and at least one heteroaryl or aromatic yl group are connected to assorted (Asia) aryl of heteroaryl groups formation by one or more singly-bound, and described assorted (Asia) aryl comprises monocyclic heteroaryl, such as furyl, thiophenyl, pyrrole radicals, imidazole radicals, pyrazolyl, thiazolyl, thiadiazolyl group, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazine radical, tetrazine base, triazolyl, tetrazole radical, furan cluck base (furazanyl), pyridine radicals, pyrazinyl, pyrimidine radicals, pyridazinyl etc., and condensed ring type heteroaryl, comprise benzofuranyl, aisaa benzothiophenyl, isobenzofuran-base, dibenzofuran group, dibenzo thiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazole base, benzoisoxazole base, benzoxazolyl, isoindolyl, indyl, indazolyl, diazosulfide base, quinolyl, isoquinolyl, cinnolines base, quinazolyl, quinoxalinyl, carbazyl, phenoxazine group, phenanthridinyl, benzodioxole group etc.In addition, " halogen " comprises F, Cl, Br and I.
In this article, the hydrogen atom that " being substituted " in " being substituted or being unsubstituted " refers in certain functional group is replaced by another atom or group (i.e. substituting group).At the R of above formula 1 and above formula 2 1to R 18, R 31to R 33, Ar 1to Ar 5and in L, the alkyl be substituted, the cycloalkyl be substituted, the alkoxyl be substituted, the aryl be substituted, the heteroaryl be substituted, the pyrene be substituted, the arlydene be substituted, the inferior heteroaryl be substituted, substituting group in the alicyclic ring of the monocycle be substituted or many rings or aromatic ring is independently of one another for being selected from least one in the group that is made up of the following: deuterium, halogen, (C1-C30) alkyl, through (C1-C30) alkyl of halogen substiuted, (C1-C30) alkoxyl, (C6-C30) aryl, through (C6-C30) aryl that (3 to 30 yuan) heteroaryl replaces, through (C6-C30) aryl that deuterium replaces, (3 to 30 yuan) heteroaryl, through (3 to 30 yuan) heteroaryl that (C6-C30) aryl replaces, through (3 to 30 yuan) heteroaryl that (C1-C30) alkyl (C6-C30) aryl replaces, (C3-C30) cycloalkyl, (5 to 7 yuan) Heterocyclylalkyl, three (C1-C30) aIkylsilyl groups, three (C6-C30) arylsilyl groups, two (C1-C30) alkyl (C6-C30) arylsilyl groups, (C1-C30) alkyl two (C6-C30) arylsilyl groups, (C2-C30) thiazolinyl, (C2-C30) alkynyl, cyano group, list or two (C1-C30) alkyl amino, list or two (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, two (C6-C30) aryl boryl (boronyl), two (C1-C30) alkyl boryl, (C1-C30) alkyl (C6-C30) aryl boryl, (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 least one of the group be made up of the following: deuterium, halogen, (C1-C6) alkyl, (C1-C6) alkyl of halogen substiuted, (C1-C6) alkoxyl, (C6-C15) aryl, through (C6-C15) aryl that deuterium replaces, (5 to 15 yuan) heteroaryl, through (5 to 15 yuan) heteroaryl that (C6-C15) aryl replaces, through (5 to 15 yuan) heteroaryl that (C1-C6) alkyl (C6-C15) aryl replaces, three (C1-C6) aIkylsilyl groups, three (C6-C15) aIkylsilyl groups, (C1-C6) alkyl two (C6-C15) arylsilyl groups, cyano group, (C1-C6) alkyl (C6-C15) aryl, and hydroxyl.
In above formula 1, R 1to R 18preferably represent hydrogen, deuterium, halogen, (C1-C10) alkyl being substituted or being unsubstituted, (C6-C20) aryl of being substituted or being unsubstituted independently of one another, or (5 to the 20 yuan) heteroaryl being substituted or being unsubstituted; Or R 1to R 5be connected to one or more adjacent substituents with form monocycle or many rings, (5 to the 20 yuan) alicyclic ring that is substituted or is unsubstituted or aromatic ring, wherein said alicyclic ring or aromatic ring can form spirane structure, and more preferably R 1to R 5represent hydrogen, deuterium, halogen, (C1-C6) alkyl, (C6-C15) aryl independently of one another, or (5 to 15 yuan) heteroaryl; Or R 1to R 5be connected to one or more adjacent substituents to form (5 to 15 yuan) alicyclic ring or the aromatic ring of monocycle or many rings, described alicyclic ring or aromatic ring are not substituted or are replaced by with methyl or phenyl, and it is fluorene structured that described alicyclic ring or aromatic ring can form spiral shell.
In above formula 1, Ar 1and Ar 2preferably represent (C6-C20) aryl being substituted or being unsubstituted independently of one another, or (5 to the 20 yuan) heteroaryl being substituted or being unsubstituted, and more preferably represent (C6-C18) aryl, halogen, (C1-C6) alkyl, (C6-C15) aryl, (5 to 15 yuan) heteroaryl of being unsubstituted or replacing through deuterium independently of one another, or (C1-C6) alkyl (C6-C15) aryl; Or (5 to 15 yuan) heteroaryl that is that be unsubstituted or that replace through (C6-C15) aryl.
In above formula 2, Ar 3preferably represent be unsubstituted or through (C1-C6) alkyl replace pyrene, (C6-C15) aryl, through deuterium replace (C6-C15) aryl, warp (C6-C15) aryl replace (5 to 15 yuan) heteroaryl, or through (C1-C6) alkyl (C6-C15) aryl replacement (5 to 15 yuan) heteroaryl.
Ar 3preferably be selected from following structure:
Wherein A represents deuterium, halogen, (C1-C30) alkyl, through (C1-C30) alkyl of halogen substiuted, (C1-C30) alkoxyl, (C6-C30) aryl, through (C6-C30) aryl that (3 to 30 yuan) heteroaryl replaces, through (C6-C30) aryl that deuterium replaces, (3 to 30 yuan) heteroaryl, through (3 to 30 yuan) heteroaryl that (C6-C30) aryl replaces, through (3 to 30 yuan) heteroaryl that (C1-C30) alkyl (C6-C30) aryl replaces, (C3-C30) cycloalkyl, (5 to 7 yuan) Heterocyclylalkyl, three (C1-C30) aIkylsilyl groups, three (C6-C30) arylsilyl groups, two (C1-C30) alkyl (C6-C30) arylsilyl groups, (C1-C30) alkyl two (C6-C30) arylsilyl groups, (C2-C30) thiazolinyl, (C2-C30) alkynyl, cyano group, list or two (C1-C30) alkyl amino, list or two (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, two (C6-C30) aryl boryl, two (C1-C30) alkyl boryl, (C1-C30) alkyl (C6-C30) aryl boryl, (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro and hydroxyl, and m represents the integer of 0 to 4.(5 to 15 yuan) heteroaryl that A preferably represents (C1-C6) alkyl, (C6-C15) aryl, (C6-C15) aryl replaced through deuterium, warp (C6-C15) aryl replace, or through (5 to 15 yuan) heteroaryl of (C1-C6) alkyl (C6-C15) aryl replacement.
In above formula 2, (C6-C20) arlydene that L preferably represents singly-bound or is substituted or is unsubstituted, and (C6-C15) arlydene more preferably representing singly-bound or be unsubstituted or replace through (C1-C6) alkyl.
In above formula 2, Ar 4and Ar 5preferably represent (C6-C20) aryl being substituted or being unsubstituted independently of one another, or (5-20 unit) heteroaryl being substituted or being unsubstituted; Or Ar 4and Ar 5be connected with nitrogen-atoms with form monocycle or many rings, (5-20 unit) alicyclic ring that is substituted or is unsubstituted or aromatic ring, and more preferably represent (C6-C18) aryl, halogen, (C1-C6) alkyl, (C1-C6) alkyl through halogen substiuted, (C1-C6) alkoxyl, (C6-C15) aryl, three (C1-C6) aIkylsilyl groups, three (C6-C15) arylsilyl groups, (C1-C6) alkyl two (C6-C15) arylsilyl groups, the cyano group that are unsubstituted or replace through deuterium independently of one another, or hydroxyl; Or (5 to the 15 yuan) heteroaryl being unsubstituted or replacing through (C6-C15) aryl; Or Ar 4and Ar 5be connected (5 to the 15 yuan) alicyclic ring or the aromatic ring that form many rings with nitrogen-atoms, described alicyclic ring or aromatic ring are unsubstituted or replace through halogen, cyano group, (C1-C6) alkyl, (C6-C15) aryl or cyano group (C6-C15) aryl.
Ar 4and Ar 5can be connected to form the ring being selected from following structure with nitrogen-atoms:
The specific compound of formula 1 includes but not limited to following compound:
The specific compound of formula 2 includes but not limited to following compound:
Compound according to formula 1 of the present invention and formula 2 is prepared by the synthetic method that those of skill in the art are known.
Organnic electroluminescent device comprises the first electrode, the second electrode, and at least one deck organic layer between the first electrode and the second electrode.Described organic layer comprises luminescent layer, and described luminescent layer comprises the combination of one or more host compounds represented by formula 1 and one or more dopant compound represented by formula 2.
One in first electrode and the second electrode can be anode, and another can be negative electrode.Described organic layer also can comprise at least one layer being selected from the group be made up of the following: hole injection layer, hole transmission layer, electron transfer layer, electron injecting layer, intermediate layer, hole blocking layer and electronic barrier layer.
Described luminescent layer is radiative layer and it can be individual layer, or it can for the multilayer be formed by stacking by two-layer or more layer.Described luminescent layer also can inject/transmission electronic/hole except utilizing emitted light.Described dopant preferably by the total amount of dopant in luminescent layer and main body with the doped in concentrations profiled being less than 17 % by weight.
In another embodiment of the present invention, main body/dopant combination of one or more host compounds represented by formula 1 and one or more dopant compound of being represented by formula 2 is provided.In addition, the organic el device comprising described main body/dopant combination is additionally provided.
In another embodiment, the invention provides the electroluminescent organic material of the main body/dopant combination of one or more host compounds comprising and represented by formula 1 and one or more dopant compound represented by formula 2, and comprise the organic el device of described material.Above-mentioned material can only be made up of the combination of formula 1 compound and formula 2 compound, or also can be included in normally used traditional material in electroluminescent organic material.
In another embodiment, the invention provides one or more host compounds comprising and represented by formula 1 and the organic layer of the combination of one or more dopant compound represented by formula 2.Described organic layer comprises plurality of layers.Described dopant compound and described host compound can be comprised in same layer, or can be comprised in different layers.In addition, the invention provides the organic el device comprising organic layer.
Except the combination of the host compound of formula 1 and the dopant compound of formula 2, also can comprise at least one compound be selected from by the group formed based on the compound of arylamine and the compound of styrene-based base arylamine according to the organic layer of organic el device of the present invention.
In organic el device according to the present invention, described organic layer also can comprise at least one metal being selected from the group be made up of the following: the organic metal of the periodic table of elements the 1st race's metal, group II metal, period 4 transition metal, period 5 transition metal, lanthanide series metal and d-transition elements, or at least one comprises the complex compound of described metal.Described organic layer also can comprise one or more luminescent layer of comprising in addition and charge generation layer.
In addition, except containing with good grounds compound of the present invention, organic el device according to the present invention carrys out transmitting white by comprising at least one deck luminescent layer further, and described luminescent layer comprises blue light electroluminescent compounds known in the art, ruddiness electroluminescent compounds or green glow electroluminescent compounds.Equally, if needed, sodium yellow or orange light luminescent layer can in described device, be comprised.
According to the present invention, preferably at least one layer (hereinafter referred to as " superficial layer ") can be placed on the inner surface of one or two electrode; Described layer is selected from chalcogenide layer, metal halide and metal oxide layer.Particularly, preferably chalcogenide (the comprising oxide) layer of silicon or aluminium is placed on the anode surface of electroluminescent medium layer, and preferably metal halide or metal oxide layer is placed on the cathode surface of electroluminescent medium layer.This type of superficial layer is that Organnic electroluminescent device provides job stability.Preferably, described chalcogenide 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 fluoride etc.; And described metal oxide comprises Cs 2o, Li 2o, MgO, SrO, BaO, CaO etc.
In organic el device according to the present invention, preferably electric transmission compound and the mixed zone of reproducibility dopant or the mixed zone of hole transport compound and oxidizability dopant are placed in electrode pair at least one on the surface.In this case, electric transmission compound is reduced into anion, and thus electronics injects from mixed zone and is transferred to electroluminescent medium and becomes and be more prone to.In addition, hole transport compound is oxidized to cation, and thus hole is injected from mixed zone and is transferred to electroluminescent medium and becomes and be more prone to.Preferably, described oxidizability dopant comprises various lewis acid (Lewisacid) and acceptor compound; Described reproducibility dopant comprises alkali metal, alkali metal compound, alkaline-earth metal, rare earth metal and composition thereof.Reproducibility dopant layer can be adopted to prepare as charge generation layer and to there is two-layer or more layer electroluminescence layer and the el light emitting device of transmitting white.
In order to form each layer according to organic el device of the present invention, dry membrane formation process can be used, as vacuum evaporation, sputtering, plasma and ion plating method, or wet membrane formation process, as spin coating, dip-coating and flow coating processes.
When using wet membrane formation process, by forming the material dissolves of each layer or diffuse in any suitable solvent and form film, described solvent is ethanol, chloroform, oxolane, diox etc. such as.Described solvent can be wherein solubilized or dispersion and forms any solvent of the material of each layer, and described solvent is no problem in film forming ability.
Hereafter describe compound of the present invention, the preparation method of described compound and the luminosity of described device in detail with reference to following instance.But these are only for illustrating embodiments of the invention, and therefore scope of the present invention can be not limited thereto.
example 1: the preparation of compound H-26
the preparation of compound 1-2
In flask after mixing cpd 1-1 (25g, 0.157mol) and HCl (10%, 840mL), stir described mixture at 0 DEG C.Subsequently by NaNO 2(11.6g, 0.168mol) is dissolved in the H of 85mL 2add in reactant mixture in O, and stir described mixture 20 minutes at 0 DEG C.Subsequently KI (52g, 0.314mol) is dissolved in the H of 165mL 2add in reactant mixture in O, and stir described mixture 3 hours at 0 DEG C.After the reaction, described mixture distilled water washs and uses ethyl acetate (EA) to extract.Use MgSO subsequently 4dry organic layer, uses rotary evaporator to remove solvent, and subsequently with column chromatography eluting surplus materials to obtain compound 1-2 (10.2g, 24%).
the preparation of compound 1-4
Compound 1-2 (9.2g, 0.034mol) to be introduced in flask and to add compound 1-3 (11g, 0.037mol), Pd (PPh 3) 4(2.0g, 0.001mol), K 2cO 3after the toluene of EtOH and 100mL of (2M, 51mL), 51mL, reactant mixture be heated to 120 DEG C and stir 8 hours.After the reaction, described mixture distilled water washs and extracts with EA.Use MgSO subsequently 4dry organic layer, uses rotary evaporator to remove solvent, and subsequently with column chromatography eluting surplus materials to obtain compound 1-4 (9.5g, 70%).
the preparation of compound 1-5
In flask mixing cpd 1-4 (9.5g, 0.024mol) and 200mL METHYLENE CHLORIDE (MC) after, 0 DEG C of stirred reaction mixture 20 minutes.Subsequently triethylamine (10mL, 0.072mol) is added in reactant mixture.Subsequently by Trifluoromethanesulfonic anhydride (OTf 2) (5.1mL, 0.031mol) to add in mixture and at room temperature to stir 6 hours.After the reaction, add 4MHCl in mixture, described mixture distilled water washing also extracts with EA.Use MgSO subsequently 4dry organic layer, uses rotary evaporator to remove solvent, and subsequently with column chromatography eluting surplus materials to obtain compound 1-5 (8.0g, 63%).
the preparation of compound H-26
Compound 1-5 (8.0g, 0.015mol) to be introduced in flask and to add compound 1-6 (2.0g, 0.016mol), Pd (PPh 3) 4(1.0g, 0.001mol), K 2cO 3after the toluene of EtOH and 50mL of (2M, 22mL), 22mL, reactant mixture be heated to 120 DEG C and stir 8 hours.After the reaction, described mixture distilled water washs and extracts with EA.Use MgSO subsequently 4dry organic layer, uses rotary evaporator to remove solvent, and subsequently with column chromatography eluting surplus materials to obtain compound H-26 (3.1g, 45%).
example 2: the preparation of compound H-47
The compound 1-5 (3.7g, 0.007mol) of example 1 to be introduced in flask and to add compound 2-1 (2.7g, 0.007mol), Pd (PPh 3) 4(465mg, 0.0004mol), K 2cO 3after the toluene of EtOH and 22mL of (2M, 11mL), 11mL, reactant mixture be heated to 120 DEG C and stir 8 hours.After the reaction, described mixture distilled water washs and extracts with EA.Use MgSO subsequently 4dry organic layer, uses rotary evaporator to remove solvent, and subsequently with column chromatography eluting surplus materials to obtain compound H-47 (3.3g, 78%).
example 3: the preparation of compound H-48
The compound 1-5 (3.7g, 0.006mol) of example 1 to be introduced in flask and to add compound 3-1 (1.3g, 0.006mol), Pd (PPh 3) 4(350mg, 0.0003mol), K 2cO 3after the toluene of EtOH and 20mL of (2M, 10mL), 10mL, reactant mixture be heated to 120 DEG C and stir 8 hours.After the reaction, described mixture distilled water washs and extracts with EA.Use MgSO subsequently 4dry organic layer, uses rotary evaporator to remove solvent, and subsequently with column chromatography eluting surplus materials to obtain compound H-48 (1.8g, 48%).
example 4: the preparation of compound H-45
The compound 1-5 (4.0g, 0.007mol) of example 1 to be introduced in flask and to add compound 4-1 (1.6g, 0.008mol), Pd (PPh 3) 4(462mg, 0.0004mol), K 2cO 3after the toluene of EtOH and 22mL of (2M, 11mL), 11mL, reactant mixture be heated to 120 DEG C and stir 8 hours.After the reaction, described mixture distilled water washs and extracts with EA.Use MgSO subsequently 4dry organic layer, uses rotary evaporator to remove solvent, and subsequently with column chromatography eluting surplus materials to obtain compound H-45 (1.7g, 43%).
example 5: the preparation of compound H-49
The compound 1-5 (3.0g, 0.005mol) of example 1 to be introduced in flask and to add compound 5-1 (1.5g, 0.006mol), Pd (PPh 3) 4(330mg, 0.0002mol), K 2cO 3after the toluene of EtOH and 22mL of (2M, 9mL), 9mL, reactant mixture be heated to 120 DEG C and stir 8 hours.After the reaction, described mixture distilled water washs and extracts with EA.Use MgSO subsequently 4dry organic layer, uses rotary evaporator to remove solvent, and subsequently with column chromatography eluting surplus materials to obtain compound H-49 (2.0g, 60%).
example 6: the preparation of compound H-1
Compound 6-1 (5.4g, 0.010mol) to be introduced in flask and to add compound 1-6 (1.4g, 0.011mol), Pd (PPh 3) 4(580mg, 0.0005mol), K 2cO 3after the toluene of EtOH and 30mL of (2M, 15mL), 15mL, reactant mixture be heated to 120 DEG C and stir 8 hours.After the reaction, described mixture distilled water washs and extracts with EA.Use MgSO subsequently 4dry organic layer, uses rotary evaporator to remove solvent, and subsequently with column chromatography eluting surplus materials to obtain compound H-1 (3.3g, 73%).
example 7: the preparation of compound H-19
The compound 6-1 (4.0g, 0.007mol) of example 6 to be introduced in flask and to add compound 4-1 (1.6g, 0.008mol), Pd (PPh 3) 4(462mg, 0.0004mol), K 2cO 3after the toluene of EtOH and 22mL of (2M, 11mL), 11mL, reactant mixture be heated to 120 DEG C and stir 8 hours.After the reaction, described mixture distilled water washs and extracts with EA.Use MgSO subsequently 4dry organic layer, uses rotary evaporator to remove solvent, and subsequently with column chromatography eluting surplus materials to obtain compound H-19 (2.7g, 67%).
example 8: the preparation of compound H-20
The compound 6-1 (3.0g, 0.005mol) of example 6 to be introduced in flask and to add compound 5-1 (1.8g, 0.008mol), Pd (PPh 3) 4(330mg, 0.0003mol), K 2cO 3after the toluene of EtOH and 20mL of (2M, 10mL), 10mL, reactant mixture be heated to 120 DEG C and stir 8 hours.After the reaction, described mixture distilled water washs and extracts with EA.Use MgSO subsequently 4dry organic layer, uses rotary evaporator to remove solvent, and subsequently with column chromatography eluting surplus materials to obtain compound H-20 (1.5g, 47%).
example 9: the preparation of compound H-21
The compound 6-1 (3.0g, 0.005mol) of example 6 to be introduced in flask and to add compound 2-1 (2.2g, 0.006mol), Pd (PPh 3) 4(346mg, 0.0003mol), K 2cO 3after the toluene of EtOH and 20mL of (2M, 10mL), 10mL, reactant mixture be heated to 120 DEG C and stir 8 hours.After the reaction, described mixture distilled water washs and extracts with EA.Use MgSO subsequently 4dry organic layer, uses rotary evaporator to remove solvent, and subsequently with column chromatography eluting surplus materials to obtain compound H-21 (2.2g, 65%).
example 10: the preparation of Compound D-8
At mixing 1,6-dibromo pyrene (5g, 13.8mmol), diphenylamines (5.8g, 34.2mmol), Pd (OAc) 2after (0.16g, 0.71mmol) and NaOtBu (6.7g, 69.7mmol), described mixture is introduced in vacuum state and blanket of nitrogen.Subsequently by P (t-Bu) 3the toluene of (1mL, 2.0mmol) and 80mL adds in reactant mixture, and 120 DEG C of return stirrings 5 hours.After the reaction, described mixture EA and distilled water extraction, and by EA/MeOH recrystallization to obtain Compound D-8 (2.5g, 9.3mmol, 30%).
example 11: the preparation of Compound D-9
Compound D-9 (4g, 50%) is in the mode similar with the synthetic method of Compound D-8, obtains by using 1,6-dibromo pyrene and 4-(phenylamino) phenylcyanide.
example 12: the preparation of Compound D-10
Compound D-10 (5.6g, 40%) is in the mode similar with the synthetic method of Compound D-8, obtains by using 6-bromo-N, N-hexichol pyrene-1-amine and N-phenyl-4-(triphenylsilyl) aniline.
example 13: the preparation of Compound D-21
1,6-dibromo pyrene (13g, 0.068mol), 4-(phenylamino) phenylcyanide (52g, 0.144mol), Cu (7.6g, 0.12mol), Cs is mixed in flask 2cO 3(54g, 0.167mol) and 18-are preced with after-6 (2.1g, 0.008mol), to be dissolved in by described mixture in 1 of 300mL, 2-dichloro-benzenes and 190 DEG C of return stirrings 12 hours.After the reaction, use distiller to remove 1,2-dichloro-benzenes, extract organic layer with EA, use magnesium sulfate to remove residual moisture, and be separated surplus materials to obtain compound 6-1 (15.5g, 50%) by column chromatography subsequently.
Obtained compound 6-1 (6g, 0.012mol), 3-(9H-carbazole-9-base) phenylboric acid (5.4g, 0.019mol), Pd (PPh is mixed in flask 3) 4(732 milligrams, 0.63mmol) and K 2cO 3after (5.2g, 0.036mol), described mixture is by adding the H of the toluene of 40mL, EtOH and 20mL of 20mL 2o and dissolve and subsequently 120 DEG C stir 7 hours.Passing through to add H lentamente 2after O completes reaction, extract organic layer with EA, use magnesium sulfate to remove residual moisture, and use column chromatography drying subsequently and be separated surplus materials to obtain Compound D-21 (4g, 50%).
example 14: the preparation of Compound D-25
Compound D-25 (1.9g, 30%) is in the mode similar with the synthetic method of Compound D-25, obtains by using compound 6-1 and (9-phenyl-9H-carbazole-3-base) boric acid.
example 15: the preparation of Compound D-32
1 is dissolved in toluene, 6-dibromo pyrene (10g, 27.8mmol), indoline (6.9mL, 61.1mmol), acid chloride (318mg, 1.4mmol), tri-butyl phosphine (0.7mL, 2.8mmol) and cesium carbonate (27g, 83.3mmol) after, mixture 24 hours described in 120 DEG C of return stirrings.After the reaction, described mixture EA extracts, with distilled water washing, by dried over mgso, and through decompression distillation.Surplus materials is separated to obtain Compound D-32 (5g, 41%) subsequently by column chromatography.
example 16: the preparation of Compound D-88
the preparation of compound 16-1
Adding acid chloride (the II) (Pd (OAc) of 3-aminobenzonitrile (50g, 423mmol), iodobenzene (39mL, 352mmol), 3.9g 2), the tri-butyl phosphine (P (t-Bu) of 8.5mL 3) and the Cs of 228g 2cO 3after in toluene, stir described mixture 24 hours at 120 DEG C.After the reaction, make described mixture progressively cool to room temperature, add H 2o in described mixture, and extracts described mixture with EA.Described organic layer Na 2sO 4drying, condensation, and be separated by column chromatography to obtain compound 16-1 (70g, 85%).
the preparation of compound 16-2
At the Cs of Cu and 34g of interpolation compound 16-1 (8g, 41mmol), 1,6-dibromo pyrene (30g, 83mmol), 4.8g 2cO 3after in 1, the 2-dichloro-benzenes of 400mL, stir described mixture 19 hours at 200 DEG C.After agitation, H is added lentamente 2to complete reaction in O to described mixture, and make described mixture cool to room temperature, add H 2o in described mixture, and extracts described mixture with EA.Described organic layer Na 2sO 4drying, condensation, and be separated by column chromatography to obtain compound 16-2 (12g, 60%).
the preparation of Compound D-88
After 1,2,3, the 4-tetrahydroquinoline of mixing cpd 16-2 (5g, 10mmol) and 1.6mL, obtain Compound D-88 (3.8g, 69%) by the synthetic method of compound 16-1.
example 17: the preparation of Compound D-149
the preparation of compound 17-1
After in interpolation 4-isobutyryl benzonitrile (6.2g, 35.7mmol) and phenylhydrazine (3.8g, 35.7mmol) to the acetic acid of 120mL, stir described mixture 3 hours at 80 DEG C.After the described mixture of cooling, add 1, the 2-dichloroethanes of 120mL in described mixture, and add sodium triacetoxy borohydride (NaBH (OAc) lentamente 3) (9.8g, 46.6mmol) in described mixture.After this, at room temperature stir described mixture 30 minutes, add H 2o in described mixture, and extracts described mixture with EA.Described organic layer Na 2sO 4drying, condensation, and be separated by column chromatography to obtain compound 17-1 (5.3g, 60%).
the preparation of Compound D-149
After mixing cpd 16-2 (5g, 10mmol) and compound 17-1 (2.5g, 20mmol), obtain Compound D-149 (4.5g, 70%) by the synthetic method of compound 16-1.
example 18: the preparation of Compound D-98
the preparation of compound 18-1
At the H of the toluene of 300mL, the ethanol (EtOH) of 100mL and 100mL 2the bromo-6-fluoroaniline (25g, 92.9mmol) of 2,4-bis-, phenylboric acid (34g, 278mmol), tetrakis triphenylphosphine palladium (Pd (PPh is dissolved in the mixed solvent of O 3) 4) (10g, 9.29mmol) and K 2cO 3after (64g, 464mmol), stir described mixture 7 hours at 120 DEG C.After the reaction, H is added lentamente 2to complete reaction in O to described mixture, and extract described mixture with EA.Organic layer Na 2sO 4dry and be separated by column chromatography to obtain compound 18-1 (20g).
the preparation of compound 18-2
Compound 18-2 (23g, 72%) is in the mode identical with the synthetic method of compound 16-1, obtains by using compound 18-1 (30g, 113.9mmol) and iodobenzene (19.3g, 94mmol).
the preparation of compound 18-3
Compound 18-3 (2.2g, 12%) is in the mode identical with the synthetic method of compound 16-2, obtains by using compound 18-2 (10g, 29.4mmol) and 1,6-dibromo pyrene (21g, 58mmol).
the preparation of Compound D-98
Compound D-98 (1g, 43%) is in the mode identical with the synthetic method of Compound D-88, obtains by using compound 18-3 (5g, 8mmol) and indoline (1mL, 9.6mmol).
example 19: the preparation of Compound D-153
Compound D-153 (1g, 40%) is in the mode identical with the synthetic method of Compound D-88, obtains by using compound 19-3 (5g, 8mmol) and 1,2,3,4-tetrahydroquinoline-6-nitrile (1.5g, 9.6mmol).
example 20: the preparation of Compound D-147
the preparation of compound 20-1
Compound 20-1 (4g, 60%) is in the mode identical with the synthetic method of compound 16-2, obtains by using compd A (3g, 8.6mmol) and 1,6-dibromo pyrene (6.2g, 17.2mmol).
the preparation of Compound D-147
Compound D-147 (2.2g, 50%) is in the mode identical with the synthetic method of compound 16-1, by using compound 20-1 (4g, 6.4mmol) He 1,2,3,4-tetrahydroquinoline-6-nitrile (1.2g, 7.7mmol) obtains.
example 21: the preparation of Compound D-148
Compound D-148 (2g, 50%) is in the mode identical with the synthetic method of compound 16-1, obtains by using compound 21-2 (6g, 12.6mmol) and 2-phenyl-1H-indoles (3g, 15.2mmol).
example 22: the preparation of Compound D-150
the preparation of compound 22-1
Compound 22-1 (12g, 52%) is in the mode identical with the synthetic method of compound 17-1, obtains by using 2-methyl isophthalic acid-phenyl-propane-1-ketone (15.7mL, 104mmol) and phenylhydrazine (15g, 104mmol).
the preparation of compound 22-2
Compound 22-2 (10.6g, 50%) is in the mode identical with the synthetic method of compound 16-2, obtains by using diphenylamines (8g, 47.3mmol) and 1,6-dibromo pyrene (34g, 94.6mmol).
the preparation of Compound D-150
Compound D-150 (12g, 52%) is in the mode identical with the synthetic method of compound 16-1, obtains by using compound 22-1 (3.1g, 13.9mmol) and compound 22-2 (7.5g, 16.7mmol).
example 23: the preparation of Compound D-144
Compound D-144 (1.5g, 20%) is in the mode identical with the synthetic method of compound 16-1, obtains by using compound 22-1 (3.1g, 13.9mmol) and compound 16-2 (6g, 12.7mmol).
example 24: the preparation of Compound D-143
the preparation of compound 24-1
Compound 24-1 (7.5g, 30%) be in the mode identical with the synthetic method of compound 17-1, by using 2-methyl isophthalic acid-phenyl-propane-1-ketone (15g, 101mmol) and obtaining cyanophenylhydrazine (17.1g, 101mmol).
the preparation of Compound D-143
Compound D-143 (1.25g, 20%) is in the mode identical with the synthetic method of compound 16-1, obtains by using compound 24-1 (2.5g, 10.1mmol) and compound 16-2 (5g, 10.6mmol).
example 25: the preparation of Compound D-164
Compound D-164 (5.4g, 78%) is in the mode identical with the synthetic method of compound 16-1, by using compound 16-2 (6.3g, 13.3mmol) He 1,2,3,4-tetrahydroquinoline-6-nitrile (2g, 12.6mmol) obtains.
Host compound H-1 to the H-62 used in organic el device and dopant compound D-1 to D-184 are to manufacture to the synthetic method that the synthetic method in example 25 is identical with example 1.The productive rate (%) of manufactured dopant compound, MS/EIMS, UV (nm) and PL (nm) are illustrated in following table 1:
[table 1]
device example 1: use and manufacture OLED device according to organic electroluminescent compounds of the present invention
Luminescent material according to the present invention is used to manufacture OLED device.First, use trichloroethylene, acetone, ethanol and distilled water to carry out Ultrasonic Cleaning to transparency electrode tin indium oxide (ITO) film (15 Ω/sq) (SCP company of Korea S (SamsungCorning)) on the glass baseplate of Organic Light Emitting Diode (OLED) device successively, be then stored in isopropyl alcohol.Then, ITO base material is arranged in the substrate holder of vacuum phase deposition equipment.By N 1, N 1 'two (the N in-([1,1 '-biphenyl]-4,4 '-two base) 1-(naphthalene-1-base)-N 4, N 4-diphenyl benzene-Isosorbide-5-Nitrae-diamines) introduce in the room of described vacuum phase deposition equipment, then by the room pressure-controlled of described equipment to 10 -6holder.Then, apply electric current to described room to evaporate the material of above-mentioned introducing, thus on ITO base material, form the hole injection layer that thickness is 60nm.Then, by N, N '-bis-(Alpha-Naphthyl)-N, N '-diphenyl-4,4 '-diamines is introduced in another room of described vacuum phase deposition equipment, and by applying electric current to evaporate to described room, thus on described hole injection layer, form the hole transmission layer that thickness is 20nm.After this, compound H-26 is incorporated into as material of main part in a room of described vacuum phase deposition equipment, and Compound D-9 is incorporated in another room as dopant.This bi-material with the evaporation of different speed and the total amount of press dopant and main body with 3 % by weight doping deposit, to form the luminescent layer that thickness is 30nm on hole transmission layer.Then, 2-(4-(9,10-bis-(naphthalene-2-base) anthracene-2-base) phenyl)-1-phenyl-1H-benzo [d] imidazoles is incorporated in a room, and is incorporated in another room by quinoline lithium.This bi-material evaporates with identical speed and deposits, to form the electron transfer layer that thickness is 30nm on luminescent layer with the doping of 50 % by weight separately.Then, after deposition quinoline lithium is the electron injecting layer of 2nm on the electron transport layer, be the Al negative electrode of 150nm by another vacuum phase deposition equipment deposit thickness on described electron injecting layer as thickness.Thus, manufacture OLED device.All material for the manufacture of described OLED device passes through before use 10 -6under holder condition, purifying is carried out in vacuum sublimation.
Manufactured OLED device shows has 2020cd/m 2brightness and 72.2mA/cm 2the blue-light-emitting of current density.Half-life is 169 hours.
device example 2: use and manufacture OLED device according to organic electroluminescent compounds of the present invention
OLED device manufactures in the mode identical with device example 1, and difference is use compound H-1 as the main body of luminescent material and use Compound D-9 as the dopant of luminescent material.
Manufactured OLED device shows has 2020cd/m 2brightness and 73.9mA/cm 2the blue-light-emitting of current density.Half-life is 162 hours.
device example 3: use and manufacture OLED device according to organic electroluminescent compounds of the present invention
OLED device manufactures in the mode identical with device example 1, and difference is use compound H-45 as the main body of luminescent material and use Compound D-9 as the dopant of luminescent material.
Manufactured OLED device shows has 2020cd/m 2brightness and 76.2mA/cm 2the blue-light-emitting of current density.Half-life is 165 hours.
device example 4: use and manufacture OLED device according to organic electroluminescent compounds of the present invention
OLED device manufactures in the mode identical with device example 1, and difference is use compound H-49 as the main body of luminescent material and use Compound D-9 as the dopant of luminescent material.
Manufactured OLED device shows has 2140cd/m 2brightness and 77.2mA/cm 2the blue-light-emitting of current density.Half-life is 164 hours.
device example 5: use and manufacture OLED device according to organic electroluminescent compounds of the present invention
OLED device manufactures in the mode identical with device example 1, and difference is use compound H-48 as the main body of luminescent material and use Compound D-9 as the dopant of luminescent material.
Manufactured OLED device shows has 1890cd/m 2brightness and 73.6mA/cm 2the blue-light-emitting of current density.Half-life is 170 hours.
device example 6: use and manufacture OLED device according to organic electroluminescent compounds of the present invention
OLED device manufactures in the mode identical with device example 1, and difference is use compound H-20 as the main body of luminescent material and use Compound D-9 as the dopant of luminescent material.
Manufactured OLED device shows has 1890cd/m 2brightness and 72.1mA/cm 2the blue-light-emitting of current density.Half-life is 178 hours.
comparative example 1: use traditional electroluminescent organic material to manufacture OLED device
OLED device manufactures in the mode identical with device example 1, and difference is use compound R-1 as the main body of luminescent material and use Compound D-9 as the dopant of luminescent material.
Manufactured OLED device shows has 1890cd/m 2brightness and 67.6mA/cm 2the blue-light-emitting of current density.Half-life is 146 hours.
As implied above, demonstrate the life characteristics using the Organnic electroluminescent device combined according to main body of the present invention and dopant to have prolongation, maintain remarkable current characteristic simultaneously.

Claims (9)

1. one or more host compounds represented by following formula 1 and the combination of one or more dopant compound that represented by following formula 2:
Wherein
R 1to R 18(C1-C30) alkyl represent hydrogen, deuterium, halogen independently of one another, being substituted or being unsubstituted, (C3-C30) cycloalkyl being substituted or being unsubstituted, (C1-C30) alkoxyl being substituted or being unsubstituted, (C6-C30) aryl being substituted or being unsubstituted, (3 to the 30 yuan) the heteroaryl ,-SiR that are substituted or are unsubstituted 31r 32r 33, cyano group or hydroxyl; Or R 1to R 5, and R 14to R 18be connected to one or more adjacent substituents with form monocycle or many rings, (3 to the 30 yuan) alicyclic ring that is substituted or is unsubstituted or aromatic ring, the carbon atom of wherein said ring can form spirane structure, and one or more carbon atoms of described ring can be selected from the hetero-atom displacement of nitrogen, oxygen and sulphur through at least one;
R 31to R 33(C1-C30) alkyl represent hydrogen, deuterium, halogen independently of one another, being substituted or being unsubstituted, (C6-C30) aryl being substituted or being unsubstituted, or (3 to the 30 yuan) heteroaryl being substituted or being unsubstituted;
Ar 1and Ar 2(C6-C30) aryl represent hydrogen, deuterium independently of one another, being substituted or being unsubstituted, or (3 to the 30 yuan) heteroaryl being substituted or being unsubstituted; Or be connected to one or more adjacent substituents with form monocycle or many rings, (3 to the 30 yuan) alicyclic ring that is substituted or is unsubstituted or aromatic ring, the carbon atom of wherein said ring can form spirane structure, and one or more carbon atoms of described ring can be selected from the hetero-atom displacement of nitrogen, oxygen and sulphur through at least one; Wherein Ar 1and Ar 2be asynchronously hydrogen; And
Described heteroaryl contains the hetero-atom that at least one is selected from B, N, O, S, P (=O), Si and P;
Wherein
Ar 3represent the pyrene being substituted or being unsubstituted;
(C6-C30) arlydene that L represents singly-bound, is substituted or is unsubstituted, or (3 to the 30 yuan) inferior heteroaryl being substituted or being unsubstituted;
Ar 4and Ar 5represent (C6-C30) aryl being substituted or being unsubstituted independently of one another, or (3 to the 30 yuan) heteroaryl being substituted or being unsubstituted; Or Ar 4and Ar 5be connected with nitrogen-atoms with form monocycle or many rings, (3 to the 30 yuan) alicyclic ring that is substituted or is unsubstituted or aromatic ring, one or more carbon atoms of described ring can be selected from the hetero-atom displacement of nitrogen, oxygen and sulphur through at least one; And
N represents the integer of 1 to 3; Wherein n is 2 or is greater than 2, each identical or different.
2. combine as claimed in claim 1, wherein in formula 1 and formula 2, R 1to R 18, R 31to R 33, Ar 1to Ar 5and the alkyl be substituted described in L, the described cycloalkyl be substituted, the described alkoxyl be substituted, the described aryl be substituted, the described heteroaryl be substituted, the described pyrene be substituted, the described arlydene be substituted, the described inferior heteroaryl be substituted, the alicyclic ring of the described monocycle that is substituted or many rings or the substituting group of aromatic ring are independently of one another for being selected from least one in the group that is made up of the following: deuterium, halogen, (C1-C30) alkyl, through (C1-C30) alkyl of halogen substiuted, (C1-C30) alkoxyl, (C6-C30) aryl, through (C6-C30) aryl that (3 to 30 yuan) heteroaryl replaces, through (C6-C30) aryl that deuterium replaces, (3 to 30 yuan) heteroaryl, through (3 to 30 yuan) heteroaryl that (C6-C30) aryl replaces, through (3 to 30 yuan) heteroaryl that (C1-C30) alkyl (C6-C30) aryl replaces, (C3-C30) cycloalkyl, (5 to 7 yuan) Heterocyclylalkyl, three (C1-C30) aIkylsilyl groups, three (C6-C30) arylsilyl groups, two (C1-C30) alkyl (C6-C30) arylsilyl groups, (C1-C30) alkyl two (C6-C30) arylsilyl groups, (C2-C30) thiazolinyl, (C2-C30) alkynyl, cyano group, list or two (C1-C30) alkyl amino, list or two (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, two (C6-C30) aryl boryl (boronyl), two (C1-C30) alkyl boryl, (C1-C30) alkyl (C6-C30) aryl boryl, (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro and hydroxyl.
3. combine as claimed in claim 1, wherein in formula 1, R 1to R 18(C1-C10) alkyl represent hydrogen, deuterium, halogen independently of one another, being substituted or being unsubstituted, (C6-C20) aryl being substituted or being unsubstituted, or (5 to the 20 yuan) heteroaryl being substituted or being unsubstituted; Or R 1to R 5be connected to one or more adjacent substituents with form monocycle or many rings, (5 to the 20 yuan) alicyclic ring that is substituted or is unsubstituted or aromatic ring, described alicyclic ring or aromatic ring can form spirane structure; And
Ar 1and Ar 2represent (C6-C20) aryl being substituted or being unsubstituted independently of one another, or (5 to the 20 yuan) heteroaryl being substituted or being unsubstituted.
4. combine as claimed in claim 1, wherein in formula 2, Ar 3represent be unsubstituted or through (C1-C6) alkyl replace pyrene, (C6-C15) aryl, through deuterium replace (C6-C15) aryl, warp (C6-C15) aryl replace (5 to 15 yuan) heteroaryl, or through (C1-C6) alkyl (C6-C15) aryl replacement (5 to 15 yuan) heteroaryl;
L represents singly-bound, or (C6-C20) arlydene being substituted or being unsubstituted; And
Ar 4and Ar 5represent (C6-C20) aryl being substituted or being unsubstituted independently of one another, or (5 to the 20 yuan) heteroaryl being substituted or being unsubstituted; Or Ar 4and Ar 5be connected with nitrogen-atoms with form monocycle or many rings, (5 to the 20 yuan) alicyclic ring that is substituted or is unsubstituted or aromatic ring.
5. combine as claimed in claim 1, wherein in formula 2, Ar 3be selected from following structure:
Wherein A represents deuterium, halogen, (C1-C30) alkyl, through (C1-C30) alkyl of halogen substiuted, (C1-C30) alkoxyl, (C6-C30) aryl, through (C6-C30) aryl that (3 to 30 yuan) heteroaryl replaces, through (C6-C30) aryl that deuterium replaces, (3 to 30 yuan) heteroaryl, through (3 to 30 yuan) heteroaryl that (C6-C30) aryl replaces, through (3 to 30 yuan) heteroaryl that (C1-C30) alkyl (C6-C30) aryl replaces, (C3-C30) cycloalkyl, (5 to 7 yuan) Heterocyclylalkyl, three (C1-C30) aIkylsilyl groups, three (C6-C30) arylsilyl groups, two (C1-C30) alkyl (C6-C30) arylsilyl groups, (C1-C30) alkyl two (C6-C30) arylsilyl groups, (C2-C30) thiazolinyl, (C2-C30) alkynyl, cyano group, list or two (C1-C30) alkyl amino, list or two (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, two (C6-C30) aryl boryl, two (C1-C30) alkyl boryl, (C1-C30) alkyl (C6-C30) aryl boryl, (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro and hydroxyl, and
M represents the integer of 0 to 4.
6. combine as claimed in claim 1, wherein in formula 2, Ar 4and Ar 5can be connected to form the ring being selected from following structure with nitrogen-atoms:
7. combine as claimed in claim 1, the wherein said compound represented by formula 1 is selected from the group be made up of the following:
8. combine as claimed in claim 1, the wherein said compound represented by formula 2 is selected from the group be made up of the following:
9. an Organnic electroluminescent device, it comprises combination as claimed in claim 1.
CN201480037637.6A 2013-07-17 2014-07-17 A combination of a dopant compound and a host compound and an organic electroluminescent device comprising the same Pending CN105359292A (en)

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