CN105829320A - Novel organic electroluminescent compound, and multi-component host material and organic electroluminescent device comprising the same - Google Patents

Novel organic electroluminescent compound, and multi-component host material and organic electroluminescent device comprising the same Download PDF

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CN105829320A
CN105829320A CN201480069533.3A CN201480069533A CN105829320A CN 105829320 A CN105829320 A CN 105829320A CN 201480069533 A CN201480069533 A CN 201480069533A CN 105829320 A CN105829320 A CN 105829320A
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substituted
unsubstituted
yuan
aryl
compound
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H-R·康
M-J·李
H-J·康
Y-G·金
Y-M·林
N-K·金
B·金
C-S·金
Y－J·曹
K-J·李
H-Y·娜
T-J·李
J-H·沈
K-H·崔
H-C·安
J-S·俊
Y-K·金
J-R·洪
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Rohm and Haas Electronic Materials Korea Ltd
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Rohm and Haas Electronic Materials Korea Ltd
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Priority claimed from KR1020130165394A external-priority patent/KR101478990B1/en
Application filed by Rohm and Haas Electronic Materials Korea Ltd filed Critical Rohm and Haas Electronic Materials Korea Ltd
Priority to CN201910202934.6A priority Critical patent/CN110078742B/en
Publication of CN105829320A publication Critical patent/CN105829320A/en
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Abstract

The present disclosure relates to a novel organic electroluminescent compound, and a multi-component host material and an organic electroluminescent device comprising the same. The organic electroluminescent compound of the present disclosure has good luminous efficiency and can be used as a host for a light-emitting layer. By using the organic electroluminescent compound according to the present disclosure, an organic electroluminescent device can have high color purity, low driving voltage, long lifespan, and improved current and power efficiencies.

Description

Novel organic electroluminescent compounds and comprise its multicomponent material of main part and Organnic electroluminescent device
Technical field
The present invention relates to novel organic electroluminescent compounds and the multicomponent material of main part comprising it and Organnic electroluminescent device.
Background technology
Electroluminescent (EL) device is a kind of selfluminous device, has an advantage in that it provides relatively wide viewing angle, bigger contrast ratio and very fast response time.Organic el device is initially researched and developed [" applied physics bulletin (Appl.Phys.Lett.) " 51 by the use little molecule of aromatic diamine and aluminium complex as the material being used for being formed luminescent layer by Eastman Kodak Company (EastmanKodak), 913,1987].
In general, organic el device has and comprises anode, negative electrode and the structure of organic layer being placed between anode and negative electrode.Hole and electronics inject organic layer from anode and negative electrode respectively；Compound is in excited state by the restructuring between hole and electronics, and the decay of excited state causes energy relaxation to arrive ground state, along with light emission.The organic layer of organic el device comprises hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer etc..Hole-injecting material, hole mobile material, electron-blocking materials, luminescent material, hole barrier materials, electron transport material, electron injection material etc. are included for preparing the material of organic layer.
The most important factor of the luminous efficiency of decision organic el device is luminescent material.Luminescent material needs have the sub-efficiency of higher amount, relatively high electron mobility and higher hole mobility.Additionally, the luminescent layer formed by luminescent material needs for uniform and stable.Depending on the color observed by light emission, luminescent material can classify as blue and green light or red emissive material, and wherein can comprise additionally in gold-tinted or orange light emissive material.Additionally, depend on excited state, luminescent material can classify as fluorescent material (singlet state) and phosphor material (triplet).Fluorescent material is widely used for organic el device.But, it is converted into the luminous efficiency four (4) times of light owing to phosphor material strengthens electricity compared to fluorescent material and power consumption can be reduced to have long lifetime, the exploitation of widely studied phosphorescent light-emitting materials.
Iridium (III) complex is referred to as phosphor material the most widely; including double (2-(2 '-benzothienyl)-pyridine root-N, C3 ') iridium (acetyl-pyruvate) ((acac) Ir (btp)2), three (2-phenylpyridine) iridium (Ir (ppy)3) and double (4,6-difluorophenyl pyridinato root-N, C2) pyridine carboxylic acid iridium (Firpic) respectively as glowing, green glow and the material of blue light.
Can be by material of main part and adulterant combination be prepared luminescent material to improve color purity, luminous efficiency and stability.When using material of main part/adulterant system as luminescent material, material of main part greatly affects efficiency and the performance of EL device, and therefore its select it is critical that.At present, 4,4 '-N, N '-two carbazoles-biphenyl (CBP) is the most widely known material of main part for phosphor material.Recently, pioneer (Pioneer) (Japanese) etc. develops use bathocuproine (bathocuproine, BCP) and aluminum (III) double (2-methyl-8-quinolinium) (4-phenylphenol salt) (BAlq) etc. is as the efficient organic el device of material of main part, described material of main part is referred to as hole barrier materials.
Although conventional phosphorescent light body material provides good luminous feature, but its have the disadvantages that (1) due to its relatively lower glass transition temperatures and undesirable heat stability, therefore its degraded may occur during high-temperature deposition process in a vacuum.(2) power efficiency of organic el device is given by [(π/voltage) × current efficiency], and described power efficiency is inversely proportional to voltage.Although the organic el device comprising phosphorescent light body material provides the current efficiency (cd/A) higher than the organic el device comprising fluorescent material, but significantly higher driving voltage is required.Therefore, for power efficiency (lm/W), there is not advantage.(3) additionally, the service life of organic el device is shorter, and remain a need for improving luminous efficiency.
Therefore, in order to provide the organic el device with desirable features, need the material selected rightly for preparing the organic layer in organic el device, specifically, for preparing main body or the adulterant of luminescent layer.
Korean Patent Application Publication 10-2010-0105099 discloses a kind of has the heterocyclic compound condensing 5 rings as the material of main part of luminescent layer.But, the Organnic electroluminescent device using the compound of described list of references is unsatisfactory in terms of power efficiency, luminous efficiency, useful life and color purity.
Summary of the invention
Technical barrier
It is an object of the present invention to provide a kind of organic electroluminescent compounds, it can provide and illustrate low driving voltage, long life, high color purity and good electric current and the Organnic electroluminescent device of power efficiency, and provides multicomponent material of main part and the Organnic electroluminescent device comprising it.
The solution of a difficult problem
The inventors discovered that, above target can be by being realized by the organic electroluminescent compounds represented with following formula 1.
Wherein Ar1Represent (3 yuan to the 30 yuan) heteroaryl being substituted or being unsubstituted or (C6-C30) aryl being substituted or being unsubstituted；
L1Represent singly-bound, (C6-C30) arlydene being substituted or being unsubstituted or (3 yuan to the 30 yuan) inferior heteroaryl being substituted or being unsubstituted；
Ring A representsRing B represents
Y represents O, S, N (R6) or C (R4)(R5)；X represents O, S, N (R6) or C (R7)(R8)；Its restrictive condition is that X and Y is not simultaneously N (R6)；
R1To R3Represent hydrogen, deuterium, halogen, cyano group, carboxyl, nitro, hydroxyl, (C1-C30) alkyl being substituted or being unsubstituted, (C3-C30) cycloalkyl being substituted or being unsubstituted, (C3-C30) cycloalkenyl group being substituted or being unsubstituted, (3 yuan to the 7 yuan) Heterocyclylalkyl being substituted or being unsubstituted, (C6-C30) aryl being substituted or being unsubstituted, (3 yuan to the 30 yuan) heteroaryl being substituted or being unsubstituted ,-NR independently of one another9R10Or-SiR11R12R13, maybe can be bonded to adjacent substituents to form (C3-C30) monocycle or multi-ring alicyclic ring or aromatic ring being substituted or being unsubstituted；
R4To R13Represent hydrogen, deuterium, halogen, (C1-C30) alkyl being substituted or being unsubstituted, (C6-C30) aryl being substituted or being unsubstituted, (3 yuan to the 30 yuan) heteroaryl being substituted or being unsubstituted, (C3-C30) cycloalkyl being substituted or being unsubstituted, (5 yuan to the 7 yuan) Heterocyclylalkyl being substituted or being unsubstituted, (C6-C30) aryl (C1-C30) alkyl being substituted or being unsubstituted ,-NR independently of one another14R15、-SiR16R17R18, cyano group, nitro or hydroxyl, maybe can be bonded to adjacent substituents to form (C3-C30) monocycle or multi-ring alicyclic ring or aromatic ring being substituted or being unsubstituted；
R14To R18Have and R4To R13Identical definition；
The carbon atom of described alicyclic ring or aromatic ring can be replaced selected from the hetero atom of nitrogen, oxygen and sulfur through at least one；
Described (sub-) heteroaryl and Heterocyclylalkyl contain at least one selected from B, N, O, S, P (=O), the hetero atom of Si and P；
A and c represents the integer of 1 to 4 independently of one another；Wherein a, b or c represent the integer of two or more, R1、R2Or R3In each may be the same or different；
Its restrictive condition, for when the above formula 1 compound is by when representing with following formula 2, can be formed at R1To R3In any one and adjacent substituents between ring for the naphthalene nucleus being substituted.
The advantageous effect of the present invention
The organic electroluminescent compounds of the present invention can provide the higher color purity compared with Conventional compounds, long lifetime and preferable luminous efficiency.Therefore, the compounds of this invention is used can to show higher color purity, relatively low driving voltage, long lifetime, preferable luminous efficiency, especially preferably current efficiency and the power consumption of improvement as the Organnic electroluminescent device of the material of main part of luminescent layer.
Detailed description of the invention
Hereinafter, will be described in detail the present invention.But, below describe and be intended to explain the present invention, and be not intended to limit by any way the scope of the present invention.
The present invention provides above formula 1 organic electroluminescent compounds, comprise described compound electroluminescent organic material and the Organnic electroluminescent device comprising described material.
Herein, " (C1-C30) (sub-) alkyl " instruction has straight or branched (sub-) alkyl of 1 to 30, preferably 1 to 20 and more preferably 1 to 10 carbon atoms, and includes methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, isobutyl group, the tert-butyl group etc.." (C2-C30) thiazolinyl " instruction has the straight or branched thiazolinyl of 2 to 30, preferably 2 to 20 and more preferably 2 to 10 carbon atoms, and includes vinyl, 1-acrylic, 2-acrylic, 1-butylene base, crotyl, 3-cyclobutenyl, 2-methyl but-2-ene base etc.." (C2-C30) alkynyl " instruction has the straight or branched alkynyl of 2 to 30, preferably 2 to 20 and more preferably 2 to 10 carbon atoms, and includes acetenyl, 1-propinyl, 2-propynyl, ethyl acetylene base, 2-butyne base, 3-butynyl, 1-methylpent-2-alkynyl etc.." (C3-C30) cycloalkyl " instruction has 3 to 30, preferably 3 to 20 and the monocycle of more preferably 3 to 7 carbon atoms or polycyclic hydrocarbon, and includes cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl etc.." (3 yuan to 7 yuan) Heterocyclylalkyl " represents have 3 to 7, preferably 5 to 7 ring backbone atoms (include that at least one is selected from B, N, O, S, P (=O), Si and P, the preferably hetero atom of O, S and N) cycloalkyl, and include oxolane, pyrrolidine, tiacyclopentane, Pentamethylene oxide. etc..In addition, " (C6-C30) (sub-) aryl " indicates the monocycle or condensed ring derived from aromatic hydrocarbon and having 6 to 30, preferably 6 to 20 and more preferably 6 to 15 ring backbone c atoms, and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthryl, indenyl, triphenylenyl, pyrenyl, naphthacenyl, base, tetraphenyl chrysenyl, thick, fluoranthene base etc.." (3 yuan to 30 yuan) (sub-) heteroaryl " instruction have 3 to 30, preferably 3 to 20 and more preferably 3 to 15 ring backbone atoms and include at least one, the heteroatomic aryl of preferably 1 to 4 groups selecting free B, N, O, S, P (=O), Si and P to form；Can be monocycle or the condensed ring condensed with at least one phenyl ring；It can be fractional saturation；Can be by by making at least one heteroaryl or aryl be connected to, through singly-bound, the group that heteroaryl is formed；nullAnd including monocyclic heteroaryl，Such as furyl、Thienyl、Pyrrole radicals、Imidazole radicals、Pyrazolyl、Thiazolyl、Thiadiazolyl group、Isothiazolyl、Isoxazolyl、Oxazolyl、Di azoly、Triazine radical、Tetrazine base、Triazolyl、Tetrazole radical、Furan a word used for translation base、Pyridine radicals、Pyrazinyl、Pyrimidine radicals、Pyridazinyl etc.，And condensed ring type heteroaryl，Such as benzofuranyl、Benzothienyl、Isobenzofuran-base、Dibenzofuran group、Dibenzothiophenes base、Benzo naphtho-furan base、Benzo aphthothiophenes base、Benzimidazolyl、Benzothiazolyl、Benzisothia oxazolyl、Benzisoxa oxazolyl、Benzoxazolyl group、Isoindolyl、Indyl、Indazolyl、Diazosulfide base、Quinolyl、Isoquinolyl、Cinnolines base、Quinazolyl、Quinoxalinyl、Carbazyl、Benzo carbazyl、Naphthyridinyl、Coffee piperazine base、Coffee piperidinyl、Benzodioxole group etc..Additionally, " halogen " includes F, Cl, Br and I.
Herein, " being substituted " in statement " be substituted or be unsubstituted " means that the hydrogen atom in a certain functional group is replaced through another atom or group (i.e. substituent group).In the formula 1 of the present invention, Ar1、L1, X, Y and R1To R3nullIn (C1-C30) alkyl being substituted、(C3-C30) cycloalkyl being substituted、(C3-C30) cycloalkenyl group being substituted、(3 yuan to the 7 yuan) Heterocyclylalkyl being substituted、(C6-C30) (sub-) aryl being substituted、(3 yuan to 30 yuan) (sub-) heteroaryl being substituted、The substituent group of (C6-C30) aryl (C1-C30) alkyl being substituted or (C3-C30) monocycle being substituted or multi-ring alicyclic ring or aromatic ring is each independently at least one selected from the group that consists of: deuterium、Halogen、Cyano group、Carboxyl、Nitro、Hydroxyl、(C1-C30) alkyl、Halogen (C1-C30) alkyl、(C2-C30) thiazolinyl、(C2-C30) alkynyl、(C1-C30) alkoxyl、(C1-C30) alkyl sulfenyl、(C3-C30) cycloalkyl、(C3-C30) cycloalkenyl group、(3 yuan to 7 yuan) Heterocyclylalkyl、(C6-C30) aryloxy group、(C6-C30) artyl sulfo、It is unsubstituted or through (C6-C30) aryl substituted (3 yuan to 30 yuan) heteroaryl、It is unsubstituted or through (3 yuan to 30 yuan) heteroaryl substituted (C6-C30) aryl、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、Amino、List or two (C1-C30) alkyl amino、List or two (C6-C30) arylamino、(C1-C30) alkyl (C6-C30) arylamino、(C1-C30) alkyl-carbonyl、(C1-C30) alkoxy carbonyl、(C6-C30) aryl carbonyl、Two (C6-C30) aryl boryl、Two (C1-C30) alkyl boryl、(C1-C30) alkyl (C6-C30) aryl boryl、(C6-C30) aryl (C1-C30) alkyl and (C1-C30) alkyl (C6-C30) aryl.
Preferably, formula 1 compound can be represented by with any one in following formula 2 to 5:
Wherein Ar1、L1、X、Y、R1To R3, a, b and c be as defined in above formula 1.
Ar1Preferably represent (5 yuan to the 20 yuan) heteroaryl being substituted or being unsubstituted or (C6-C20) aryl being substituted or being unsubstituted.Ar1The substituent group being substituted group can be (C6-C20) aryl, (6 yuan to 20 yuan) heteroaryl or single or two (C6-C20) arylamino.According to one embodiment of present invention, Ar1Nitrogenous (5 yuan to the 20 yuan) heteroaryl being substituted or being unsubstituted can be represented；And specifically, it is selected from the group consisted of: the triazine radical being substituted or being unsubstituted, the pyrimidine radicals being substituted or being unsubstituted, the pyridine radicals being substituted or being unsubstituted, the pyrazinyl being substituted or being unsubstituted, the quinolyl being substituted or being unsubstituted, the isoquinolyl being substituted or being unsubstituted, the quinazolyl being substituted or being unsubstituted, the naphthyridinyl being substituted or being unsubstituted and the quinoxalinyl being substituted or being unsubstituted.In the embodiment above, Ar1The substituent group of the group being substituted preferably for (C6-C20) aryl or (5 yuan to 20 yuan) heteroaryl, and specifically, can be at least one in phenyl, naphthyl, biphenyl, benzofuranyl, benzothienyl, dibenzofuran group and dibenzothiophenes base.
L1(C6-C20) arlydene preferably represent singly-bound, being substituted or being unsubstituted or (5 yuan to the 20 yuan) inferior heteroaryl being substituted or being unsubstituted；And more preferably singly-bound or (C6-C20) arlydene of being substituted or being unsubstituted.Specifically, L1Singly-bound, the phenylene being substituted or being unsubstituted, the biphenylene being substituted or being unsubstituted or the naphthylene being substituted or being unsubstituted can be represented.
Preferably, X and Y is selected from O, S and N (R independently of one another6)；Its restrictive condition is that X and Y is not simultaneously N (R6).According to one embodiment of present invention, X and Y is selected from O and S independently of one another.According to another embodiment of the invention, X and Y is selected from O and S independently of one another；And at least one Wei the S in X and Y.R6Preferably represent (C6-C30) aryl being substituted or being unsubstituted, and specifically, the phenyl being substituted or being unsubstituted, the naphthyl being substituted or being unsubstituted or the biphenyl being substituted or being unsubstituted.
R1To R3The most preferably represent hydrogen, deuterium, (C1-C20) alkyl being substituted or being unsubstituted, (C3-C20) cycloalkyl being substituted or being unsubstituted, (C6-C30) aryl being substituted or being unsubstituted, (3 yuan to the 30 yuan) heteroaryl being substituted or being unsubstituted ,-NR9R10Or-SiR11R12R13, maybe can be bonded to adjacent substituents to form (C3-C30) monocycle or multi-ring alicyclic ring or aromatic ring being substituted or being unsubstituted.It is highly preferred that R1To R3Monocycle or Ppolynuclear aromatic ring in definition are not naphthalene nucleus and phenanthrene ring.R9To R13Preferably represent (C6-C30) aryl being substituted or being unsubstituted.Specifically, R1To R3Hydrogen can be represented.
According to one embodiment of present invention, Ar1Represent (5 yuan to the 20 yuan) heteroaryl being substituted or being unsubstituted or (C6-C20) aryl being substituted or being unsubstituted；L1Represent singly-bound, (C6-C20) arlydene being substituted or being unsubstituted or (5 yuan to the 20 yuan) inferior heteroaryl being substituted or being unsubstituted；R1To R3Represent hydrogen, deuterium, (C1-C20) alkyl being substituted or being unsubstituted, (C3-C20) cycloalkyl being substituted or being unsubstituted, (C6-C30) aryl being substituted or being unsubstituted, (3 yuan to the 30 yuan) heteroaryl being substituted or being unsubstituted ,-NR independently of one another9R10Or-SiR11R12R13, maybe can be bonded to neighbouring substituent group to form (C3-C30) monocycle or multi-ring alicyclic ring or aromatic ring being substituted or being unsubstituted.
The compound represented by formula 1 includes the following, but is not limited to this.
The organic electroluminescent compounds of the present invention can be prepared by synthetic method known to those skilled in the art, such as bromation, suzuki reaction (Suzukireaction), Buchwald-Hartwig reaction (Buchwald-Hartwigreaction), ullmann reaction (Ullmannreaction) etc..For example, formula 1 compound can be prepared as follows: after five (5) the ring condensed compounds that preparation is represented by formula A, formula A compound experience bromation, it is thus achieved that the compound represented by formula B；Formula B compound condenses with indenes ring, indole ring, benzofuran ring or benzothiophene ring, it is thus achieved that the mother nucleus structure of formula 1；And *-L1-Ar1It is then connected to prepared mother nucleus structure, thus obtains formula 1 compound.
In formula A and B, X and Y is selected from O, S, N (R independently of one another6)、C(R4)(R5) and C (R7)(R8)。
Can explanation in following reaction process 1 to 4 for preparing the method for the compounds of this invention mentioned above.
[reaction process 1]
[reaction process 2]
[reaction process 3]
[reaction process 4]
In above reaction process 1 to 4, X is selected from O, S, N (R6) and C (R7)(R8)。
According to a further aspect in the invention, it is provided that the electroluminescent organic material of contained 1 organic electroluminescent compounds and the Organnic electroluminescent device comprising described material.
Described material can comprise one or more compounds selected from formula 1 organic electroluminescent compounds.Described material can further include and comprises the Conventional compounds for electroluminescent organic material.Electroluminescent organic material is preferably for material of main part.When electroluminescent organic material is used as material of main part, it can further include the second material of main part in addition to formula 1 compound of the present invention, and its details provide hereinafter.
The Organnic electroluminescent device of the present invention can comprise the first electrode, the second electrode and at least one organic layer being placed between the first electrode and the second electrode, and wherein said organic layer can comprise at least one formula 1 compound.
One in first and second electrodes can be anode, and another one can be negative electrode.Described organic layer can comprise luminescent layer, and can further include at least one selected from hole injection layer, hole transmission layer, electronic barrier layer, electron transfer layer, electron injecting layer, interlayer, electron buffer layer and the layer of hole blocking layer.
Formula 1 organic electroluminescent compounds of the present invention can be included in luminescent layer as material of main part.Preferably, luminescent layer can further include at least one adulterant.Preferably, in addition to formula 1 organic electroluminescent compounds (the first material of main part) of the present invention, luminescent layer also can comprise the second material of main part.In view of driving voltage, useful life and luminous efficiency, the weight ratio between the first material of main part and the second material of main part is in the range of 1: 99 to 99: 1, and preferably in the range of 30: 70 to 70: 30.
According to a further aspect in the invention, it is provided that for preparing the material of Organnic electroluminescent device.Described material comprises the compound of the present invention.Described material can be the material of the luminescent layer for preparing Organnic electroluminescent device.When the compound of the present invention is included in the material of the luminescent layer preparing Organnic electroluminescent device, the compound of the present invention can be included as material of main part.When the compound of the present invention is included as material of main part, material can further include the second material of main part.In view of driving voltage, useful life and luminous efficiency, the weight ratio between the compounds of this invention and the second material of main part is in the range of 1: 99 to 99: 1, and preferably in the range of 30: 70 to 70: 30.Described material can be compositions or mixture.
In art, known phosphorescent light body material can be used as the second material of main part.In view of driving voltage, useful life and luminous efficiency, the compound of the group that choosing freely forms using the compound of following formula 6 to 10 is preferred as the second material of main part.
Wherein Cz represents following structure:
L4Represent singly-bound, (C6-C30) arlydene being substituted or being unsubstituted or (5 yuan to the 30 yuan) inferior heteroaryl being substituted or being unsubstituted；M represents (C6-C30) aryl being substituted or being unsubstituted or (5 yuan to the 30 yuan) heteroaryl being substituted or being unsubstituted；Y1And Y2Represent-O-,-S-,-N (R independently of one another31)-or-C (R32)(R33Its restrictive condition of)-, is Y1And Y2Can not exist simultaneously；X represents O or S；R21To R24Represent hydrogen, deuterium, halogen, cyano group, (C1-C30) alkyl being substituted or being unsubstituted, (C3-C30) cycloalkyl being substituted or being unsubstituted, (C6-C30) aryl being substituted or being unsubstituted, (5 yuan to the 30 yuan) heteroaryl being substituted or being unsubstituted or R independently of one another25R26R27Si-；Maybe can be bonded to adjacent substituents can replace selected from the hetero atom of nitrogen, oxygen and sulfur through at least one with formation (C3-C30) monocycle or multi-ring alicyclic ring or aromatic ring, its carbon atom；Its restrictive condition is when the h of the formula 6 or i of formula 7 is 1, R23Or R24It is formed without the Y containing formula 8 and 91Or Y2Ring, and the R of formula 1022It is formed without the R of the formula of being connected to 8 and 921Indole ring；R25To R27Represent (C1-C30) alkyl being substituted or being unsubstituted or (C6-C30) aryl being substituted or being unsubstituted independently of one another；R31To R33(C1-C30) alkyl represent hydrogen independently of one another, being substituted or being unsubstituted, (C6-C30) aryl being substituted or being unsubstituted or (5 yuan to the 30 yuan) heteroaryl being substituted or being unsubstituted；Maybe can be bonded to adjacent substituents can replace selected from the hetero atom of nitrogen, oxygen and sulfur through at least one with formation (C5-C30) monocycle or multi-ring alicyclic ring or aromatic ring, its carbon atom；R32And R33May be the same or different；(sub-) heteroaryl contains at least one selected from B, N, O, S, P (=O), the hetero atom of Si and P；H and i represents the integer of 1 to 3 independently of one another；J, k, l and m represent the integer of 0 to 4 independently of one another；And when the integer that h, i, j, k, l or m are two or more, each (Cz-L4), each (Cz), each R21, each R22, each R23Or each R24May be the same or different.
Preferably, in formula 6 to 10, M can represent nitrogenous (6 yuan to the 20 yuan) heteroaryl being substituted or being unsubstituted.Preferably, the substituent group being substituted group of M can be (C1-C20) alkyl；It is unsubstituted or through (C1-C10) alkyl, three (C6-C13) aryl-silane base or (6 yuan to 13 yuan) heteroaryl substituted (C6-C24) aryl；Or be unsubstituted or through (C1-C10) alkyl, three (C6-C13) aryl-silane base or (C6-C24) aryl substituted (6 yuan to 20 yuan) heteroaryl；Or three (C6-C20) aryl-silane base.Specifically, M can represent the pyridine radicals being substituted or being unsubstituted, the pyrimidine radicals being substituted or being unsubstituted, the triazine radical being substituted or being unsubstituted, the pyrazinyl being substituted or being unsubstituted, the quinolyl being substituted or being unsubstituted, the isoquinolyl being substituted or being unsubstituted, the quinazolyl being substituted or being unsubstituted, the quinoxalinyl being substituted or being unsubstituted, the naphthyridinyl being substituted or being unsubstituted or the coffee quinoline base being substituted or being unsubstituted.
Preferably, the R of formula 6 and 723And R24In at least one or the R of formula 8 to 1021And R22nullIn at least one can represent the carbazyl being substituted or being unsubstituted、The benzo carbazyl being substituted or being unsubstituted、The dibenzothiophenes base being substituted or being unsubstituted、The benzo aphthothiophenes base being substituted or being unsubstituted、The dibenzofuran group being substituted or being unsubstituted、The benzo naphtho-furan base being substituted or being unsubstituted、Carbazyl substituted (C6-C18) aryl through being substituted or being unsubstituted、Benzo carbazyl substituted (C6-C18) aryl through being substituted or being unsubstituted、Dibenzothiophenes base substituted (C6-C18) aryl through being substituted or being unsubstituted、Benzo aphthothiophenes base substituted (C6-C18) aryl through being substituted or being unsubstituted、Dibenzofuran group substituted (C6-C18) aryl through being substituted or being unsubstituted、Or benzo naphtho-furan base substituted (C6-C18) aryl through being substituted or being unsubstituted.When M is aryl, R23And R24In at least one or R21And R22In at least one can represent nitrogenous (6 yuan to the 20 yuan) heteroaryl being substituted or being unsubstituted；Maybe can have nitrogenous (6 yuan to 20 yuan) the heteroaryl alternatively base being substituted or being unsubstituted.Specifically, it is substituted or the nitrogen-containing hetero aryl that is unsubstituted can represent the pyridine radicals being substituted or being unsubstituted, the pyrimidine radicals being substituted or being unsubstituted, the triazine radical being substituted or being unsubstituted, the pyrazinyl being substituted or being unsubstituted, the quinolyl being substituted or being unsubstituted, the isoquinolyl being substituted or being unsubstituted, the quinazolyl being substituted or being unsubstituted, the quinoxalinyl being substituted or being unsubstituted, the naphthyridinyl being substituted or being unsubstituted or the coffee quinoline base being substituted or being unsubstituted.
Specifically, the second material of main part can represent with following formula 11 by above formula 6 and or rather.
Wherein A1And A2Represent (C6-C30) aryl being substituted or being unsubstituted independently of one another；Its restrictive condition is A1And A2The substituent group being substituted group for nitrogen-containing hetero aryl；
L2Represent singly-bound or (C6-C30) arlydene being substituted or being unsubstituted；And
Z1To Z16nullRepresent hydrogen independently of one another、Deuterium、Halogen、Cyano group、(C1-C30) alkyl being substituted or being unsubstituted、(C2-C30) thiazolinyl being substituted or being unsubstituted、(C2-C30) alkynyl being substituted or being unsubstituted、(C3-C30) cycloalkyl being substituted or being unsubstituted、(C6-C60) aryl being substituted or being unsubstituted、(3 yuan to the 30 yuan) heteroaryl being substituted or being unsubstituted、Three (C1-C30) alkyl tin groups, alkyl silane groups being substituted or being unsubstituted、Three (C6-C30) the aryl-silane base being substituted or being unsubstituted、Two (C1-C30) alkyl (C6-C30) the aryl-silane base being substituted or being unsubstituted、(C1-C30) alkyl two (C6-C30) the aryl-silane base being substituted or being unsubstituted、Or the list that is substituted or is unsubstituted or two (C6-C30) arylamino；Maybe can be bonded to adjacent substituents to form (C3-C30) monocycle or multi-ring alicyclic ring or aromatic ring being substituted or being unsubstituted.
According to one embodiment of present invention, formula 11 compound can be represented by any one in following formula 12,13,14 and 15.
Wherein A1、A2、L2And Z1To Z16As defined in above formula 11.
A1And A2The most preferably represent (C6-C18) aryl being substituted or being unsubstituted, and be more preferably unsubstituted or through cyano group, halogen, (C1-C6) alkyl, (C6-C12) aryl or three (C6-C12) aryl-silane base substituted (C6-C18) aryl.Specifically, A1And A2It is selected from the group being made up of the following independently of one another: the phenyl being substituted or being unsubstituted, the biphenyl being substituted or being unsubstituted, the terphenyl being substituted or being unsubstituted, the naphthyl being substituted or being unsubstituted, the fluorenyl being substituted or being unsubstituted, the benzo fluorenyl being substituted or being unsubstituted, the phenanthryl being substituted or being unsubstituted, the anthryl being substituted or being unsubstituted, the indenyl being substituted or being unsubstituted, the triphenylenyl being substituted or being unsubstituted, the pyrenyl being substituted or being unsubstituted, the naphthacenyl being substituted or being unsubstituted, the base being substituted or being unsubstituted, be substituted or be unsubstituted is chrysenyl, the phenyl napthyl being substituted or being unsubstituted, the naphthylphenyl being substituted or being unsubstituted and the fluoranthene base being substituted or being unsubstituted.A1And A2The substituent group being substituted group (phenyl being such as substituted) can be cyano group, halogen, (C1-C6) alkyl, (C6-C12) aryl or three (C6-C12) aryl-silane base.
Z1To Z16The most preferably represent hydrogen, cyano group, (C1-C10) alkyl being substituted or being unsubstituted, (C6-C20) aryl being substituted or being unsubstituted, (5 yuan to the 20 yuan) heteroaryl being substituted or being unsubstituted or three (C6-C12) the aryl-silane base being substituted or being unsubstituted.Z1To Z16The most more preferably represent hydrogen；Cyano group；(C1-C10) alkyl；It is unsubstituted or through cyano group, (C1-C10) alkyl or three (C6-C12) aryl-silane base substituted (C6-C20) aryl；It is unsubstituted or through (C1-C10) alkyl, (C6-C15) aryl or three (C6-C12) aryl-silane base substituted (5 yuan to 20 yuan) heteroaryl；Or be unsubstituted or through (C1-C10) alkyl substituted three (C6-C12) aryl-silane base.Specifically, Z1To Z16Hydrogen can be represented independently of one another；Cyano group；(C1-C6) alkyl；It is unsubstituted or through cyano group, (C1-C6) alkyl or the substituted phenyl of tri-phenyl-silane base, biphenyl, terphenyl or naphthyl；It is unsubstituted or through (C1-C6) alkyl, phenyl, biphenyl, naphthyl or tri-phenyl-silane base substituted dibenzothiophenes base or dibenzofuran group；Or be unsubstituted or through (C1-C6) alkyl substituted tri-phenyl-silane base.
L2Preferably represent singly-bound or (C6-C15) arlydene being substituted or being unsubstituted.Specifically, L2Singly-bound, the phenylene being substituted or being unsubstituted, the naphthylene being substituted or being unsubstituted or the biphenylene being substituted or being unsubstituted can be represented.
According to one embodiment of present invention, A1And A2(C6-C18) aryl being substituted or being unsubstituted can be represented independently of one another；Z1To Z16Hydrogen, cyano group, (C1-C10) alkyl being substituted or being unsubstituted, (C6-C20) aryl being substituted or being unsubstituted, (5 yuan to the 20 yuan) heteroaryl being substituted or being unsubstituted or three (C6-C12) the aryl-silane base being substituted or being unsubstituted can be represented independently of one another；And L2Singly-bound or (C6-C15) arlydene being substituted or being unsubstituted can be represented.
Specifically, formula 6 to 10 preferred embodiment of the second material of main part represented includes the following, but is not limited to this:
(wherein, TPS represents tri-phenyl-silane base.)
Adulterant is preferably at least one phosphorescent dopants.Unrestricted for the phosphorescent dopant material of the Organnic electroluminescent device of the present invention, but iridium (Ir), osmium (Os), copper (Cu) or the metallization complex compound of platinum (Pt) can be preferably chosen from, it is more preferably selected from iridium (Ir), osmium (Os), copper (Cu) or the ortho-metalated complex compound of platinum (Pt), and is even more preferably still ortho-metalated iridium complex compound.
The adulterant being included in the Organnic electroluminescent device of the present invention can select the group that the compound represented by free following formula 16 to 18 forms.
Wherein L is selected from following structure:
R100Represent hydrogen, (C1-C30) alkyl being substituted or being unsubstituted or (C3-C30) cycloalkyl being substituted or being unsubstituted；R101To R109And R111To R123Represent hydrogen, deuterium, halogen independently of one another, be unsubstituted or through (C1-C30) alkyl of halogen substiuted, (C3-C30) cycloalkyl being substituted or being unsubstituted, cyano group, (C6-C30) aryl being substituted or being unsubstituted or (C1-C30) alkoxyl being substituted or being unsubstituted；R106To R109The condensed ring that adjacent substituents is substituted with formation or is unsubstituted, the fluorenes being such as substituted or being unsubstituted, the dibenzothiophenes being substituted or being unsubstituted or the dibenzofurans being substituted or being unsubstituted can be bonded to；R120To R123The condensed ring that adjacent substituents is substituted with formation or is unsubstituted, the quinoline being such as substituted or being unsubstituted can be bonded to；R124To R127Represent hydrogen, deuterium, halogen, (C1-C30) alkyl being substituted or being unsubstituted or (C6-C30) aryl being substituted or being unsubstituted independently of one another；R124To R127The condensed ring that adjacent substituents is substituted with formation or is unsubstituted, the fluorenes being such as substituted or being unsubstituted, the dibenzothiophenes being substituted or being unsubstituted or the dibenzofurans being substituted or being unsubstituted can be bonded to；R201To R211Represent hydrogen, deuterium, halogen independently of one another, be unsubstituted or through (C1-C30) alkyl of halogen substiuted, (C3-C30) cycloalkyl being substituted or being unsubstituted or (C6-30) aryl being substituted or being unsubstituted, R208To R211The condensed ring that adjacent substituents is substituted with formation or is unsubstituted, the fluorenes being such as substituted or being unsubstituted, the dibenzothiophenes being substituted or being unsubstituted or the dibenzofurans being substituted or being unsubstituted can be bonded to；F and g represents the integer of 1 to 3 independently of one another；When the integer that f or g is two or more, R100In each may be the same or different；And n represents the integer of 1 to 3.
Specifically, phosphorescent dopant material includes following:
According to a further aspect in the invention, it is provided that a kind of Organnic electroluminescent device, it comprises anode, negative electrode and the organic layer being placed between anode and negative electrode, and wherein said organic layer comprises one or more luminescent layer；At least one luminescent layer comprises one or more dopant compound and two or more host compounds；And the first host compound in the two or more kinds of host compound is the organic electroluminescent compounds represented by formula 1.
In view of driving voltage, useful life and luminous efficiency, when Organnic electroluminescent device comprises two kinds of host compounds, weight ratio between first material of main part and the second material of main part is in the range of 1: 99 to 99: 1, and preferably in the range of 30: 70 to 70: 30.
According to one embodiment of present invention, in Organnic electroluminescent device, the first host compound in two or more host compounds can be the organic electroluminescent compounds represented by formula 1, and the compound that the optional free style 6 to 10 of the second host compound represents.
According to another embodiment of the invention, in Organnic electroluminescent device, the first host compound in two or more host compounds can be the organic electroluminescent compounds represented by formula 1, and the second host compound can be the compound represented by formula 11.
According to another embodiment of the invention, in Organnic electroluminescent device, the compound that the optional free style 12 to 15 of one or more dopant compound represents.
The Organnic electroluminescent device of the present invention is contained 1 compound in organic layer.The Organnic electroluminescent device of the present invention can further include the compound of at least one group selecting free Amines and styryl Amines composition.
In the Organnic electroluminescent device of the present invention, in addition to formula 1 compound, organic layer can also comprise at least one further selected from the metal of group consisted of: the 1st race's metal, group II metal, the 4th row transition metals, the 5th row transition metals, lanthanide series and the organic metal of d-transition elements of periodic chart, or at least one comprises the complex compounds of described metal.
Additionally, the Organnic electroluminescent device of the present invention can launch white light by comprising at least one luminescent layer further, and described luminescent layer also comprises known blue light electroluminescent compounds, HONGGUANG electroluminescent compounds or green glow electroluminescent compounds in art in addition to the compounds of this invention.If desired, it can comprise orange light luminescent layer or Yellow light emitting layer further.
In the Organnic electroluminescent device of the present invention, it is preferable that at least one layer (hereinafter, " surface layer ") is placed on the inner surface of one or two electrode, selected from chalcogenide layer, metal halide and metal oxide layer.Specifically, chalcogenide (the including oxide) layer of silicon or aluminum is preferably located on the anode surface in electroluminescent intermediate layer, and metal halide or metal oxide layer are preferably located on the cathode surface in electroluminescent intermediate layer.This type of surface layer provides operational stability for Organnic electroluminescent device.Preferably, chalcogenide includes SiOx(1≤X≤2)、AlOx(1≤X≤1.5), SiON, SiAlON etc.；Metal halide includes LiF, MgF2、CaF2, rare earth metal fluoride etc.；And metal-oxide includes Cs2O、Li2O, MgO, SrO, BaO, CaO etc..
In the Organnic electroluminescent device of the present invention, the mixed zone of electron transport compound and the mixed zone of reproducibility adulterant or hole transport compound and oxidisability adulterant can be placed at least one surface of pair of electrodes.In this case, electron transport compound is reduced to anion, and therefore injects electronics and be transferred to it electroluminescent medium from mixed zone become to be more prone to.Additionally, hole transport compound is oxidized to cation, and therefore injects hole and be transferred to it electroluminescent medium from mixed zone become to be more prone to.Preferably, oxidisability adulterant includes various lewis acid (Lewisacid) and acceptor compound；And also originality adulterant includes alkali metal, alkali metal compound, alkaline-earth metal, rare earth metal and its mixture.Reproducibility dopant layer can serve as charge generation layer to be had two or more luminescent layers with preparation and launches the el light emitting device of white light.
In order to form each layer of the Organnic electroluminescent device of the present invention, it is possible to use dry film forming method, such as vacuum evaporation, sputter, plasma and ion plating method；Or wet membrane formation method, such as ink jet printing, nozzle print, slot coated, rotary coating, dip coated and flowing coating process.
When using wet type film build method, thin film can be formed by the material forming each layer is dissolved or is diffused in any suitable solvent, described solvent such as ethanol, chloroform, oxolane, dioxane etc..Solvent can be that the material of each layer of formation can dissolve or be spread in wherein and there is not any solvent of film forming ability problem.
In the Organnic electroluminescent device of the present invention, two or more host compounds for luminescent layer can coevaporation or mixture evaporation.In this article, the method that coevaporation instruction deposits as a mixture for making two or more materials, by each in the two or more kinds of material being incorporated in corresponding crucible unit, and apply electric current so that each evaporation in described material is carried out to described unit.In this article, the method that mixture evaporation instruction deposits as a mixture for making two or more materials, by the two or more kinds of material are mixed in a crucible unit, deposit subsequently, and apply electric current to described unit so that the evaporation of described mixture is carried out.
The Organnic electroluminescent device of the application of the invention, can produce display system or illuminator.
Hereinafter, by with reference to the organic electroluminescent compounds of the following instance specific explanations present invention, the preparation method of compound and the characteristics of luminescence of device.
Example 1: prepare compound C-1 and C-3
Prepare compound 1-1
By compound 4-bromine dibenzothiophenes (50g, 189.98mmol), 2-methylthiophenyi boric acid (31.9g, 189.89mmol), tetrakis triphenylphosphine palladium (11g, 9.499mmol), sodium carbonate (60g, 569.94mmol), after toluene (900mL), ethanol (280mL) and distilled water (280mL) be incorporated in reaction vessel, at 120 DEG C, stir mixture 3 hours.After reacting, mixture distilled water wash and being extracted with ethyl acetate.It is dried gained organic layer with magnesium sulfate, and removes solvent by rotary evaporator from it.By column chromatography purified product, it is thus achieved that compound 1-1 (58g, 99%).
Prepare compound 1-2
By compound 1-1 (58g, after 189.98mmol) being dissolved in oxolane (THF) (500mL) and acetic acid (580mL), hydrogen peroxide (35%) (23mL) is slowly added dropwise in mixture.It is stirred at room temperature mixture 10 hours.After reacting, enriched mixture is to remove solvent, and extracts with dichloromethane and pure water.Residual moisture magnesium sulfate removes from the organic layer obtained, and is then dried by organic layer, concentrates, and is directly used in next reaction.
Prepare compound 1-3
After being dissolved in trifluoromethayl sulfonic acid (300mL) by compound 1-2 (58g), it is stirred at room temperature mixture 2 days, and is then added dropwise in the solution of pyridine (600mL)/pure water (1.5mL).Warm mixture, and continue 4 hours under reflux at 120 DEG C.After reacting, mixture dichloromethane extracts.The organic layer obtained passes through column chromatography purification, it is thus achieved that compound 1-3 (15.4g, 28%).
Prepare compound 1-4
After being dissolved in chloroform (550mL) by compound 1-3 (15.4g, 53.03mmol), mixture is cooled to 0 DEG C.Bromine (2.7mL, 53.03mmol) is slowly added dropwise in mixture.After reacting, mixture is slowly warming to room temperature, and stirs 8 hours.After reacting, bromine is by using sodium thiosulfate solution to remove from mixture.Filtration product, it is thus achieved that compound 1-4 (12.8g, 65.4%).
Prepare compound 1-5
By compound 1-4 (12.8g, 34.66mmol), chloroaniline (4.7mL, 45.06mmol), acid chloride (0.31g, 45.06mmol), tert-butyl group phosphine (50%) (1.4mL, 2.77mmol) with sodium tert-butoxide (8.3g, after 86.65mmol) being incorporated in toluene (170mL), stirring mixture 1 day under reflux.After reacting, mixture is cooled to room temperature, and extracts by distilled water and ethyl acetate.The organic layer obtained under reduced pressure distills, and by column chromatography purification, it is thus achieved that compound 1-5 (13.7g, 77%).
Prepare compound 1-6
By compound 1-5 (13.7g, 32.94mmol), acid chloride (0.4g, 1.646mmol), thricyclohexyl tetrafluoroborate (C18H34P.BF4) after (1.21g, 3.29mmol), cesium carbonate (32.1g, 98.82mmol) and dimethyl acetylamide (DMA) (250mL) be incorporated in reaction vessel, at 180 DEG C, stir mixture 7 hours.After reacting, mixture is extracted with ethyl acetate.The organic layer magnesium sulfate obtained is dried, and under reduced pressure distills, and by column chromatography purification, it is thus achieved that compound 1-6 (5.6g, 45%).
Prepare compound C-1
By compound 1-6 (5g, 13.17mmol), compound 1-7 (4.6g, 15.81mmol), acid chloride (1.2g, 5.27mmol), 50% tert-butyl group phosphine (5mL, 10.54mmol) with cesium carbonate (13g, after 39.5mmol) being dissolved in toluene (65mL), mixture is made to continue 3 hours at 130 DEG C under reflux.After reacting, mixture dichloromethane/pure water extraction, and by column chromatography purification, it is thus achieved that compound C-1 (4.4g, 57%).
UV:319nm, PL:525nm, fusing point: 261 DEG C, MS/EIMS experiment value 584；Value of calculation 583
Prepare compound C-3
By compound 1-6 (1.6g, 4.21mmol) with compound 1-8 (1.7g, after 6.32mmol) being dissolved in dimethylformamide (DMF) (30mL), by NaH (0.5g, 12.63mmol, 60% in mineral oil) add in mixture.Described mixture is stirred at room temperature 12 hours, and methanol and distilled water are added to wherein.The solid obtained under reduced pressure is filtered, and by column chromatography purification, it is thus achieved that compound C-3 (1.4g, 54%).
UV:342nm, PL:528nm, fusing point: 360 DEG C, MS/EIMS experiment value 611；Value of calculation 610
Example 2: prepare compound C-9 and C-11
Prepare compound 2-1
By compound 4-bromine dibenzofurans (50g, 202.35mmol), 2-methylthiophenyi boric acid (34g, 202.35mmol), tetrakis triphenylphosphine palladium (11.7g, 10.117mmol), sodium carbonate (64g, 607.06mmol), after toluene (1000mL), ethanol (300mL) and distilled water (300mL) be incorporated in reaction vessel, at 120 DEG C, stir mixture 3 hours.After reacting, mixture distilled water wash and being extracted with ethyl acetate.It is dried extracted organic layer with magnesium sulfate, and removes solvent by rotary evaporator from it.Product passes through column chromatography purification, it is thus achieved that compound 2-1 (58g, 99%).
Prepare compound 2-2
After compound 2-1 (58g, 202.35mmol) is dissolved in THF (580mL) and acetic acid (580mL), hydrogen peroxide (35%) (26mL) is slowly added dropwise in mixture.Mixture is stirred at room temperature 10 hours, concentrates to remove solvent, and then with dichloromethane and pure water extraction.Residual moisture magnesium sulfate removes from the organic layer obtained, and concentrates, and is directly used in next reaction.
Prepare compound 2-3
While stirring compound 2-2, the solution of pyridine (600mL)/pure water (1.5mL) is added dropwise to wherein.Then warm mixture, and continue 4 hours under reflux at 120 DEG C.After reacting, mixture dichloromethane extracts, and the organic layer experience column chromatography obtained, it is thus achieved that compound 2-3 (48.6g, 93%).
Prepare compound 2-4
After being dissolved in chloroform (800mL) by compound 2-3 (43.6g, 158.9mmol), mixture is cooled to 0 DEG C.Bromine (8.55mL, 166.87mmol) is slowly added dropwise in mixture.After the addition, make mixture slowly be warming to room temperature, and stir 8 hours.After reacting, bromine is by using sodium thiosulfate solution to remove from mixture.Filtration product, it is thus achieved that compound 2-4 (44g, 70%).
Prepare compound 2-5
By compound 2-4 (20g, 56.62mmol), chloroaniline (7.7mL, 73.61mmol), acid chloride (0.5g, 2.26mmol), tert-butyl group phosphine (50%) (2.2mL, 4.53mmol) with sodium tert-butoxide (13.6g, after 141.55mmol) being incorporated in toluene (280mL), mixture is stirred under reflux 1 day.After reacting, mixture is cooled to room temperature, and extracts by distilled water and ethyl acetate.The organic layer obtained under reduced pressure distills, and by column chromatography purification, it is thus achieved that compound 2-5 (11g, 48.6%).
Prepare compound 2-6
By compound 2-5 (11g, 27.5mmol), acid chloride (0.3g, 1.37mmol), C18H34P.BF4After (1g, 2.75mmol), cesium carbonate (26g, 82.5mmol) and DMA (135mL) are incorporated in reaction vessel, at 180 DEG C, stir mixture 7 hours.After reacting, mixture is extracted with ethyl acetate.The organic layer magnesium sulfate obtained is dried, and under reduced pressure distills, and by column chromatography purification, it is thus achieved that compound 2-6 (4g, 40%).
Prepare compound C-9
By compound 2-6 (3.5g, 9.63mmol), compound 1-7 (2.78g, 11.55mmol), acid chloride (0.86g, 3.85mmol), 50% tert-butyl group phosphine (3.7mL, 7.704mmol) with cesium carbonate (9.4g, after 28.8mmol) being dissolved in toluene (100mL), mixture is made to continue 3 hours at 130 DEG C under reflux.After reacting, mixture dichloromethane/pure water extraction, and by column chromatography purification, it is thus achieved that compound C-9 (2.5g, 46%).
UV:296nm, PL:535nm, fusing point: 290 DEG C, MS/EIMS experiment value 568；Value of calculation 567
Prepare compound C-11
By compound 2-6 (3g, after 8.2mmol) being dissolved in dimethylformamide (DMF) (40mL) with compound 1-8 (2.65g, 9.9mmol), by NaH (1g, 24.76mmol, 60% in mineral oil) add to wherein.It is stirred at room temperature mixture 12 hours, and in mixture, adds methanol and distilled water.The solid obtained under reduced pressure is filtered, and by column chromatography purification, it is thus achieved that compound C-11 (3.1g, 63%).
UV:342nm, PL:532nm, fusing point: 353 DEG C, MS/EIMS experiment value 595；Value of calculation 594
Example 3: prepare compound C-15
Prepare compound 1-1
After benzo [b] [1] benzo cyano group [2,3-g] benzofuran (30g, 109mmol) and chloroform (540mL) being incorporated in flask, mixture is cooled to 0 DEG C.Bromine (5.8mL, 114mmol) is slowly added dropwise in mixture.It is followed by stirring for mixture 3 hours.After reacting, mixture is extracted with ethyl acetate, and is dried with magnesium sulfate, and under reduced pressure distills.Product is separated with mixture by column chromatography, it is thus achieved that compound 1-1 (23g, productivity: 60%).
Prepare compound 1-2
By compound 1-1 (18g, 52.1mmol), 2-chloroaniline (8.2mL, 78.1mmol), acid chloride (1.1g, 5.21mmol), tri-butyl phosphine (5mL) (50%) (10.4mmol), sodium tert-butoxide (15g, after 156mmol) being incorporated in flask with toluene (260mL), stirring mixture 4 hours under reflux.After reacting, mixture dichloromethane (MC) extracts, and is dried with magnesium sulfate, and under reduced pressure distills.Product is separated with mixture by column chromatography, it is thus achieved that compound 1-2 (18g, productivity: 90%).
Prepare compound 1-3
By compound 1-2 (18g, 47.0mmol), acid chloride (1.0g, 4.70mmol), thricyclohexyl tetrafluoroborate (3.4g, 9.40mmol), cesium carbonate (46g, after 141mmol) being incorporated in flask with dimethyl acetylamide (240mL), stirring mixture 4 hours under reflux.After reacting, mixture dichloromethane (MC) extracts, and is dried with magnesium sulfate, and under reduced pressure distills.Product is separated with mixture by column chromatography, it is thus achieved that compound 1-3 (6.7g, productivity: 40%).
Prepare compound C-15
By compound 1-3 (3g, 8.25mmol) with compound B (3.4g, after in the dimethylformamide (DMF) (40mL) 10.7mmol) being dissolved in flask, by NaH (1g, 24.76mmol, 60% in mineral oil) add in mixture.Then it is stirred at room temperature mixture 12 hours, and methanol and distilled water are added to wherein.The solid obtained under reduced pressure is filtered, and by column chromatography purification, it is thus achieved that compound C-15 (3.6g, 67%).
Molecular weight (MW) UV PL Fusing point (MP)
C-15 644.74 344nm 535nm 378℃
Example 4: prepare compound C-101
Prepare compound 1-1
After benzo [b] [1] benzo cyano group [2,3-g] benzofuran (30g, 109mmol) and chloroform (540mL) being incorporated in flask, mixture is cooled to 0 DEG C.Bromine (5.8mL, 114mmol) is slowly added dropwise in mixture.It is followed by stirring for mixture 3 hours.After reacting, mixture is extracted with ethyl acetate.The organic layer sodium sulfate obtained is dried, and under reduced pressure distills.Product is separated with mixture by column chromatography, it is thus achieved that compound 1-1 (23g, productivity: 60%).
Prepare compound 1-2
By compound 1-1 (18g, 52.1mmol), 2-chloroaniline (8.2mL, 78.1mmol), acid chloride (1.1g, 5.21mmol), tri-butyl phosphine (5mL) (50%) (10.4mmol), sodium tert-butoxide (15g, after 156mmol) being incorporated in flask with toluene (260mL), stirring mixture 4 hours under reflux.After reacting, mixture dichloromethane (MC) extracts, and is dried with magnesium sulfate, and under reduced pressure distills.Product is separated with mixture by column chromatography, it is thus achieved that compound 1-2 (18g, productivity: 90%).
Prepare compound 1-3
By compound 1-2 (18g, 47.0mmol), acid chloride (1.0g, 4.70mmol), thricyclohexyl tetrafluoroborate (3.4g, 9.40mmol), cesium carbonate (46g, after 141mmol) being incorporated in flask with dimethyl acetylamide (240mL), stirring mixture 4 hours under reflux.After reacting, mixture dichloromethane (MC) extracts, and is dried with magnesium sulfate, and the most under reduced pressure distills.Product is separated with mixture by column chromatography, it is thus achieved that compound 1-3 (6.7g, productivity: 40%).
Prepare compound C-101
By compound 1-3 (6.7g, 18.4mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (7.8g, 20.2mmol), three (two sub-phenylmethylacetones) two palladium (0.8g, 0.92mmol), tri-butyl phosphine (0.9mL) (50%) (1.84mmol), sodium tert-butoxide (4.4g, after 46.1mmol) being incorporated in flask with toluene (100mL), stirring mixture 3 hours under reflux.After reacting, mixture dichloromethane (MC) extracts, and is dried with magnesium sulfate, and under reduced pressure distills.Product is separated with mixture by column chromatography, it is thus achieved that compound C-101 (8.3g, productivity: 67%).
MW UV PL M.P
C-101 670.78 390nm 541nm 382℃
[device example 1] uses the OLED of the compounds of this invention
OLED uses the organic electroluminescent compounds of the present invention to manufacture as follows.Sequentially use trichloro ethylene, acetone, ethanol and distilled water that transparency electrode tin indium oxide (ITO) thin film (15 Ω/sq) in the glass substrate of Organic Light Emitting Diode (OLED) device (Geomatec) is carried out ultrasonic washing, and be then stored in isopropanol.Then, ITO substrate is arranged on the substrate holder of vacuum phase deposition equipment.By N1, N1′Double (the N of-([1,1 '-biphenyl]-4,4 '-diyl)1-(naphthalene-1-base)-N4, N4-diphenyl benzene-Isosorbide-5-Nitrae-diamidogen) introduce in the unit of described vacuum phase deposition equipment, and then by the Stress control in the chamber of described equipment to 10-6Torr.Hereafter, to described unit applying electric current to evaporate material introduced above, thus forming thickness on ITO substrate is the hole injection layer of 60nm.Subsequently by N, N '-two (4-biphenyl)-N, N '-two (4-biphenyl)-4,4 '-benzidine is incorporated in another unit of described vacuum phase deposition equipment, and make it evaporate by applying electric current to described unit, thus forming thickness on hole injection layer is the hole transmission layer of 20nm.Hereafter, compound C-1 is introduced in a unit of vacuum phase deposition equipment as main body, and compound D-87 is introduced in another unit as adulterant.Bi-material is made to evaporate with different rates, so that the doping deposition of described adulterant 4 weight % based on the total amount by main body and adulterant is to form the thickness luminescent layer as 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 unit, and is incorporated in another unit by quinolyl lithium.Bi-material is made to evaporate with phase same rate, so that it deposits to form the thickness electron transfer layer as 30nm on luminescent layer with the doping of 50 weight % respectively.After deposition quinolyl lithium is as the electron injecting layer that thickness is 2nm on electron supplying layer, then pass through the Al negative electrode that another vacuum phase deposition equipment deposit thickness on described electron injecting layer is 150nm.Therefore, OLED is produced.It is all by 10 for manufacturing all material of OLED-6The lower vacuum sublimation of torr carrys out those materials of purification.Manufactured OLED device showing luminance under the driving voltage of 3.6V is 1,050cd/m2Red emission and electric current density be 8.1mA/cm2.Being reduced to the minimum time needed for the 90% of brightness under 5,000nit is 200 hours.
[comparative example 1] uses the OLED of conventional organic electroluminescent compounds
In addition to the compound A-1 that will be set out below and compound D-88 is used as main body and adulterant, in the way of identical with device example 1, manufacture OLED.Manufactured OLED device showing luminance under the driving voltage of 3.8V is 980cd/m2Red emission and electric current density be 16.4mA/cm2.Being reduced to the minimum time needed for the 90% of brightness under 5,000nit is 12 hours.
[comparative example 2] uses the OLED of conventional organic electroluminescent compounds
In addition to the compound A-2 that will be set out below and compound D-88 is used as main body and adulterant, in the way of identical with device example 1, manufacture OLED.Manufactured OLED device showing luminance under the driving voltage of 4.1V is 1,020cd/m2Red emission and electric current density be 13.1mA/cm2.Being reduced to the minimum time needed for the 90% of brightness under 5,000nit is 10 hours.
[comparative example 3] uses the OLED of conventional organic electroluminescent compounds
In addition to the compound A-3 that will be set out below and compound D-87 is used as main body and adulterant, in the way of identical with device example 1, manufacture OLED.Manufactured OLED device showing luminance under the driving voltage of 4.2V is 1,110cd/m2Red emission and electric current density be 9.8mA/cm2.Being reduced to the minimum time needed for the 90% of brightness under 5,000nit is 10 hours.
As confirmed above, the organic electroluminescent compounds of the present invention provides relatively low driving voltage, long lifetime and preferable current efficiency compared with conventional organic electroluminescent compounds.The Organnic electroluminescent device using the organic electroluminescent compounds of the present invention shows superiority at driving voltage, useful life and luminescence feature (especially electric current and power efficiency) aspect.
First host compound of [device example 1-1 to 1-7] the application of the invention and the coevaporation of the second host compound The OLED manufactured
OLED uses the luminescent material of the present invention to manufacture as follows.Sequentially use trichloro ethylene, acetone, ethanol and distilled water that transparency electrode tin indium oxide (ITO) thin film (10 Ω/sq) in the glass substrate of Organic Light Emitting Diode (OLED) device (Geomatec) is carried out ultrasonic washing, and be then stored in isopropanol.Then ITO substrate is arranged on the substrate holder of vacuum phase deposition equipment.By N4, N4′-diphenyl-N4, N4′-bis-(9-phenyl-9H-carbazole-3-base)-[1,1 '-biphenyl]-4,4 '-diamidogen (HI-1) introduces in the unit of vacuum phase deposition equipment, and is then 10 by the Stress control in apparatus cavity-6Torr.Hereafter, apply the electric current material with the above-mentioned introducing of evaporation to described unit, on ITO substrate, thus form the first hole injection layer that thickness is 80nm.Then, by Isosorbide-5-Nitrae, 5,8,9,12-six azepine benzophenanthrene-pregnancy nitrile (HI-2) introduces another unit of vacuum phase deposition equipment, and evaporates by applying a current to described unit, thus forms the second hole injection layer that thickness is 5nm on the first hole injection layer.By N-([1,1 '-biphenyl]-4-base)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-base) phenyl)-9H-fluorenes-2-amine (HT-1) is incorporated in a unit of vacuum phase deposition equipment, and evaporate by applying electric current to described unit, thus on the second hole injection layer, form the first hole transmission layer that thickness is 10nm.Then, by N, N-bis-([1,1 '-biphenyl]-4-base)-4 '-(9H-carbazole-9-base)-[1,1 '-biphenyl]-4-amine (HT-2) is incorporated in another unit of vacuum phase deposition equipment, and evaporate by applying a current to described unit, thus on the first hole transmission layer, form the second hole transmission layer that thickness is 60nm.As for material of main part, the two kinds of compounds shown in table 1 below are introduced between in two unit of vacuum phase deposition equipment as the first host compound and the second host compound.The dopant compound shown in table 1 is incorporated in another unit.Two kinds of host compounds evaporate with the phase same rate of 1: 1, and adulterant is with the speed evaporation different from host compound, the doping making adulterant 3 weight % based on the total amount by main body and adulterant deposits, to form the thickness luminescent layer as 40nm on hole transmission layer.By 2,4-double (9,9-dimethyl-9H-fluorenes-2-base)-6-(naphthalene-2-base)-1,3,5-triazine (ET-1) and quinolyl lithium (EI-1) are introduced between in two unit of vacuum phase deposition equipment, and evaporate with the phase same rate of 1: 1, thus forming thickness on luminescent layer is the electron transfer layer of 30nm.After deposition quinolyl lithium (EI-1) is as the electron injecting layer that thickness is 2nm on the electron transport layer, then pass through the Al negative electrode that another vacuum phase deposition equipment deposit thickness on described electron injecting layer is 80nm.
[comparative example 1-1 to 1-4] uses the second host compound as the OLED of unique main body
In addition to only the second host compound shown in table 1 below is used as the main body of luminescent layer, in the way of identical with device example 1-1 to 1-7, manufacture OLED.
[comparative example 2-1 to 2-2] uses the first host compound as the OLED of unique main body
In addition to only the first host compound shown in table 1 below is used as the main body of luminescent layer, in the way of identical with device example 1-1 to 1-7, manufacture OLED.
The feature of the Organnic electroluminescent device manufactured in device example 1-1 to 1-7, comparative example 1-1 to 1-4 and comparative example 2-1 to 2-2 is shown in table 1 below.
[table 1]
When being compared with the device of comparative example 2-2 to 2-2 by the device of comparative example 1-1 to 1-4, a kind of organic electroluminescent compounds of the use present invention shows improvement as the Organnic electroluminescent device of material of main part in terms of driving voltage, current efficiency, color purity and useful life.But, when device example 1-1 to 1-7 is compared with comparative example 1-1 to 1-4,2-1 and 2-2, the multicomponent material of main part of the organic electroluminescent compounds that Organnic electroluminescent device comprises the present invention by use and show the brilliance in terms of the performance of Organnic electroluminescent device, especially useful life.It is to say, use the Organnic electroluminescent device of multicomponent material of main part can show long lifetime compared with the Organnic electroluminescent device using a kind of host compound.

Claims (9)

1. an organic electroluminescent compounds, it represents by with following formula 1:
Wherein Ar1Represent (3 yuan to the 30 yuan) heteroaryl being substituted or being unsubstituted or (C6-C30) aryl being substituted or being unsubstituted；
L1Represent singly-bound, (C6-C30) arlydene being substituted or being unsubstituted or (3 yuan to the 30 yuan) inferior heteroaryl being substituted or being unsubstituted；
Ring A representsRing B represents
Y represents O, S, N (R6) or C (R4)(R5)；X represents O, S, N (R6) or C (R7)(R8)；Its restrictive condition is that X and Y is not simultaneously N (R6)；
R1To R3Represent hydrogen, deuterium, halogen, cyano group, carboxyl, nitro, hydroxyl, (C1-C30) alkyl being substituted or being unsubstituted, (C3-C30) cycloalkyl being substituted or being unsubstituted, (C3-C30) cycloalkenyl group being substituted or being unsubstituted, (3 yuan to the 7 yuan) Heterocyclylalkyl being substituted or being unsubstituted, (C6-C30) aryl being substituted or being unsubstituted, (3 yuan to the 30 yuan) heteroaryl being substituted or being unsubstituted ,-NR independently of one another9R10Or-SiR11R12R13, maybe can be bonded to adjacent substituents to form (C3-C30) monocycle or multi-ring alicyclic ring or aromatic ring being substituted or being unsubstituted；
R4To R13Represent independently of one another hydrogen, deuterium, halogen, (C1-C30) alkyl being substituted or being unsubstituted, (C6-C30) aryl being substituted or being unsubstituted, (3 yuan to the 30 yuan) heteroaryl being substituted or being unsubstituted, (C3-C30) cycloalkyl being substituted or being unsubstituted, (5 yuan to the 7 yuan) Heterocyclylalkyl being substituted or being unsubstituted, (C6-C30) aryl (C1-C30) alkyl being substituted or being unsubstituted ,-NR14R15、-SiR16R17R18, cyano group, nitro or hydroxyl, maybe can be bonded to adjacent substituents to form (C3-C30) monocycle or multi-ring alicyclic ring or aromatic ring being substituted or being unsubstituted；
R14To R18Have and R4To R13Identical definition；
The carbon atom of described alicyclic ring or aromatic ring can be replaced selected from the hetero atom of nitrogen, oxygen and sulfur through at least one；Described (sub-) heteroaryl and Heterocyclylalkyl contain at least one selected from B, N, O, S, P (=O), the hetero atom of Si and P；
A, b and c represent the integer of 1 to 4 independently of one another；Wherein a, b or c represent the integer of two or more, R1、R2Or R3In each may be the same or different；And
Its restrictive condition, for when the above formula 1 compound is by when representing with following formula 2, can be formed at R1To R3In any one and adjacent substituents between ring for the naphthalene nucleus being substituted.
Organic electroluminescent compounds the most according to claim 1, wherein said formula 1 compound is represented by with any one in following formula 2 to 5:
Wherein Ar1、L1、X、Y、R1To R3, a, b and c be as defined in claim 1.
Organic electroluminescent compounds the most according to claim 1, wherein
Ar1Represent (5 yuan to the 20 yuan) heteroaryl being substituted or being unsubstituted or (C6-C20) aryl being substituted or being unsubstituted；
L1Represent singly-bound, (C6-C20) arlydene being substituted or being unsubstituted or (5 yuan to the 20 yuan) inferior heteroaryl being substituted or being unsubstituted；And
R1To R3Represent hydrogen, deuterium, (C1-C20) alkyl being substituted or being unsubstituted, (C3-C20) cycloalkyl being substituted or being unsubstituted, (C6-C30) aryl being substituted or being unsubstituted, (3 yuan to the 30 yuan) heteroaryl being substituted or being unsubstituted ,-NR independently of one another9R10Or-SiR11R12R13, maybe can be bonded to adjacent substituents to form (C3-C20) monocycle or multi-ring alicyclic ring or aromatic ring.
Organic electroluminescent compounds the most according to claim 1, wherein said formula 1 compound is selected from the group consisted of:
5. an Organnic electroluminescent device, it comprises organic electroluminescent compounds according to claim 1.
6. an Organnic electroluminescent device, it comprises anode, negative electrode and the organic layer being placed between described anode and described negative electrode, and wherein said organic layer comprises one or more luminescent layer；At least one luminescent layer comprises one or more dopant compound and two or more host compounds；And the first host compound in the two or more kinds of host compound is according to the organic electroluminescent compounds represented by formula 1 described in claim 1.
Organnic electroluminescent device the most according to claim 6, the first host compound in two or more host compounds wherein said is the described organic electroluminescent compounds represented by formula 1, and the second host compound is the compound selecting free following formula 6 to 10 to represent.
Wherein Cz represents following structure:
L4Represent singly-bound, (C6-C30) arlydene being substituted or being unsubstituted or (5 yuan to the 30 yuan) inferior heteroaryl being substituted or being unsubstituted；
M represents (C6-C30) aryl being substituted or being unsubstituted or (5 yuan to the 30 yuan) heteroaryl being substituted or being unsubstituted；
Y1And Y2Represent-O-,-S-,-N (R independently of one another31)-or-C (R32)(R33Its restrictive condition of)-, is Y1And Y2Can not exist simultaneously；
X represents O or S；
R21To R24Represent hydrogen, deuterium, halogen, cyano group, (C1-C30) alkyl being substituted or being unsubstituted, (C3-C30) cycloalkyl being substituted or being unsubstituted, (C6-C30) aryl being substituted or being unsubstituted, (5 yuan to the 30 yuan) heteroaryl being substituted or being unsubstituted or R independently of one another25R26R27Si-；Maybe can be bonded to adjacent substituents can replace selected from the hetero atom of nitrogen, oxygen and sulfur through at least one with formation (C3-C30) monocycle or multi-ring alicyclic ring or aromatic ring, its carbon atom；Its restrictive condition is when the h of the formula 6 or i of formula 7 is 1, R23Or R24It is formed without the Y containing formula 8 and 91Or Y2Ring, and the R of formula 1022It is formed without the R of the formula of being connected to 8 and 921Indole ring；
R25To R27Represent (C1-C30) alkyl being substituted or being unsubstituted or (C6-C30) aryl being substituted or being unsubstituted independently of one another；
R31To R33(C1-C30) alkyl represent hydrogen independently of one another, being substituted or being unsubstituted, (C6-C30) aryl being substituted or being unsubstituted or (5 yuan to the 30 yuan) heteroaryl being substituted or being unsubstituted；Maybe can be bonded to adjacent substituents can replace selected from the hetero atom of nitrogen, oxygen and sulfur through at least one with formation (C5-C30) monocycle or multi-ring alicyclic ring or aromatic ring, its carbon atom；R32And R33May be the same or different；
Described (sub-) heteroaryl contains at least one selected from B, N, O, S, P (=O), the hetero atom of Si and P；
H and i represents the integer of 1 to 3 independently of one another；J, k, l and m represent the integer of 0 to 4 independently of one another；And when the integer that h, i, j, k, l or m are two or more, each (Cz-L4), each (Cz), each R21, each R22, each R23Or each R24May be the same or different.
Organnic electroluminescent device the most according to claim 7, wherein said second host compound is represented by with following formula 11.
Wherein A1And A2Represent (C6-C30) aryl being substituted or being unsubstituted independently of one another；Its restrictive condition is A1And A2Described in be substituted the substituent group of group for nitrogen-containing hetero aryl；
L2Represent singly-bound or (C6-C30) arlydene being substituted or being unsubstituted；And
Z1To Z16nullRepresent hydrogen independently of one another、Deuterium、Halogen、Cyano group、(C1-C30) alkyl being substituted or being unsubstituted、(C2-C30) thiazolinyl being substituted or being unsubstituted、(C2-C30) alkynyl being substituted or being unsubstituted、(C3-C30) cycloalkyl being substituted or being unsubstituted、(C6-C60) aryl being substituted or being unsubstituted、(3 yuan to the 30 yuan) heteroaryl being substituted or being unsubstituted、Three (C1-C30) alkyl tin groups, alkyl silane groups being substituted or being unsubstituted、Three (C6-C30) the aryl-silane base being substituted or being unsubstituted、Two (C1-C30) alkyl (C6-C30) the aryl-silane base being substituted or being unsubstituted、(C1-C30) alkyl two (C6-C30) the aryl-silane base being substituted or being unsubstituted、Or the list that is substituted or is unsubstituted or two (C6-C30) arylamino；Maybe can be bonded to adjacent substituents to form (C3-C30) monocycle or multi-ring alicyclic ring or aromatic ring being substituted or being unsubstituted.
Organnic electroluminescent device the most according to claim 7, the wherein said compound represented by formula 6 to 10 is selected from the group consisted of:
Wherein TPS represents tri-phenyl-silane base.
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