CN102933530A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDF

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CN102933530A
CN102933530A CN2011800243671A CN201180024367A CN102933530A CN 102933530 A CN102933530 A CN 102933530A CN 2011800243671 A CN2011800243671 A CN 2011800243671A CN 201180024367 A CN201180024367 A CN 201180024367A CN 102933530 A CN102933530 A CN 102933530A
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aryl
ring
yuan
alkyl
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安熙春
徐美兰
赵英俊
权赫柱
金奉玉
金圣珉
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Rohm and Haas Electronic Materials Korea Ltd
Rohm and Haas Electronic Materials LLC
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Rohm and Haas Electronic Materials Korea Ltd
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Abstract

Disclosed are organic electroluminescent compounds and organic electroluminescent devices employing said compounds. The organic electroluminescent compounds of the invention are defined by chemical formula [1], Chemical Formula 1 The compounds, when used in an electron transport layer of an organic electroluminescent device, reduce power consumption and operation voltage of said device. Provided are novel organic electroluminescent compounds and an organic electroluminescent device using the same. Since the organic electroluminescent compound exhibits good luminous efficiency and excellent life property, it may be used to manufacture OLED devices having very superior operation life and consuming less power due to improved power efficiency.

Description

The organic electroluminescence device of new organic electroluminescent compounds and this compound of use
Technical field
The organic electroluminescence device that the present invention relates to new organic electroluminescent compounds and use this compound more specifically, relates to as the new organic electroluminescent compounds of electroluminescent material and the organic electroluminescence device that uses this compound.
Technical background
In display device, electroluminescent (EL) device is favourable, because they provide contrast gradient and the quick speed of response of wide visual angle, excellence as the self-emission display device.Eastman Kodak Co (EastmanKodak) has at first developed a kind of organic EL device in 1987, this device uses low molecular weight aromatic diamines and aluminum complex as the material [Appl.Phys.Lett.51,913,1987] that forms electroluminescence layer.
Organic EL device is the device with following characteristic, and in the time of when electric charge is applied to the organic membrane that forms between electron injection electrode (negative electrode) and hole injecting electrode (anode) on, electronics and hole form pairing, then buries in oblivion also luminous.Can at the clear flexible base material, for example form this device on the plastics.Compare plasm display panel or inorganic EL indicating meter, described device can be worked under low voltage (being no more than 10V) and lower watt consumption condition, has simultaneously good purity of color.Because organic electroluminescent (EL) device can show three kinds of colors (green, blue and red), they have been considered to follow-on full-color display spare.
In organic EL device, determine that the greatest factor of its performance (comprising luminous efficiency and working life) is electroluminescent material.The ask for something of electroluminescent material comprises the anti-decomposability in high solid-state electroluminescent quantum yield, high electronics and hole mobility, the vacuum deposition process, ability and the stability of formation uniform thin film.
Usually, organic EL device generally has the structure of anode/hole injection layer (HIL)/hole transport layer (HTL)/emissive material layer (EML)/electron transport layer (ETL)/electron injecting layer (EIL)/negative electrode.Can be according to the organic electroluminescence device that how to form luminous material layer and form blue light-emitting, green glow or ruddiness.
In function aspects, described electroluminescent material can be divided into substrate material and dopant material.Usually, knownly provide excellent EL character by doping agent being doped to the electroluminescence layer that makes in the matrix.At present, develop the organic EL device with high-level efficiency and long service live and just becoming a urgent task.In particularly considering to the required EL performance level of large size oled panel, need in a hurry exploitation compare existing electroluminescent material excellence many materials.
Simultaneously, for conventional blue material, since the emerging product of bright dipping company (Idemitsu-Kosan) develops diphenylacetylene biphenyl (DPVBi) (compound a), developed many materials and realized commercialization.Except the blue material system of the emerging product of bright dipping company, known in addition dinaphthyl anthracene (DNA, compound b), four uncle Ding Ji perylene (compound c) systems etc.But, also tackle these materials and research and develop widely.
Distyryl based compound [distryl compound] system of the emerging product of bright dipping company is known to have the highest so far efficient, and power efficiency is 6lm/W, and the active parts life-span was greater than 30,000 hours.But when being applied to full-color display, owing to the prolongation of purity of color with the working hour descends, its life-span only has several thousand hours.In blue coloured electroluminous situation, if the electroluminescent wavelength moves to longer wavelength, it is favourable to become aspect luminous efficiency.But, this material is applied to high-quality indicating meter and is not easy, reason is blue purity of color and unsatisfactory.In addition, because the problem of purity of color, efficient and thermostability aspect, in the urgent need to this class material is researched and developed.
Figure BDA00002415256500021
Therefore, material commonly used does not form the thin film layer of matrix-doping agent, but forms individual layer.And, determine that from purity of color and efficient their commercial applications have difficulty.The authentic data that to also have a problem be the long lifetime aspect is not enough.
Similarly, for green fluorescent material, developed and be widely used following system: with coumarin derivatives (compound d, C545T), quinacridone derivative (Verbindung), DPT (compound f) mix as the Alq of matrix with percentum to tens as doping agent.The initial luminous efficiency performance level that these electroluminescent materials commonly used demonstrate can be used for commercialization.Yet, on the rapid decline of initial luminous efficiency and the working life problem is arranged also.Therefore, green fluorescent material has limitation, is difficult to adopt in the high-performance panel of giant-screen.
Figure BDA00002415256500031
In addition, because green fluorescent material does not have enough working lives for the OLED device, the more stable substrate material that needs exploitation to have high-performance.
Summary of the invention
Technical problem
Therefore, in order to address the above problem, the purpose of this invention is to provide the organic electroluminescent compounds that a kind of luminous efficiency and device service life as compared current material improve to some extent and have good skeleton (backbone) and suitable chromaticity coordinates.Another object of the present invention provides uses organic electroluminescent compounds as the organic electroluminescence device of electroluminescent material.
Technical scheme
One total aspect, the invention provides a kind of organic electroluminescent compounds that is represented by Chemical formula 1 and the organic electroluminescence device that uses this compound.Because organic electroluminescent compounds of the present invention has superior luminous efficiency and good life properties, it can be used for making the OLED device, and this device has very superior working life and because the watt consumption that improved power efficiency causes is low.
Chemical formula 1
Figure BDA00002415256500032
Wherein
R 1To R 2Represent independently hydrogen, deuterium, halogen, have or do not have substituent (C1-C30) alkyl, have or do not have substituent (C6-C30) aryl, have or do not have substituent (C3-C30) heteroaryl or have or do not have substituent five yuan to the seven membered heterocyclic alkyl;
R 3To R 11Represent independently hydrogen, deuterium, halogen, have or do not have substituent (C1-C30) alkyl, have or do not have substituent (C6-C30) aryl, have or do not have substituent (C3-C30) heteroaryl, have or do not have substituent five yuan to seven membered heterocyclic alkyl, cyano group, nitro, hydroxyl ,-NR 21R 22,-BR 23R 24,-PR 25R 26,-P (=O) R 27R 28,-SiR 29R 30R 31Perhaps-YR 32
R 12To R 19Represent independently hydrogen, deuterium, halogen, has or do not have substituent (C1-C30) alkyl, has or do not have substituent (C6-C30) aryl, have or do not have substituent (C3-C30) Cycloalkylfused replacement or unsubstituted (C6-C30) aryl with one or more, has or do not have substituent (C3-C30) heteroaryl, has or do not have the first Heterocyclylalkyl of substituent 5-to 7-, with one or more 5-to 7-unit Heterocyclylalkyls that have or do not have substituent aromatic ring to condense, has or do not have substituent (C3-C30) cycloalkyl, with one or more (C3-C30) cycloalkyl that have or do not have substituent aromatic ring to condense, cyano group, nitro, hydroxyl,-NR 21R 22,-BR 23R 24,-PR 25R 26,-P (=O) R 27R 28,-SiR 29R 30R 31,-YR 32Has or do not have substituent (C6-C30) aryl (C1-C30) alkyl, has or do not have substituent (C2-C30) thiazolinyl, has or do not have substituent (C2-C30) alkynyl, perhaps each in them can by with or do not have the replacement of condensed ring or unsubstituted (C3-C30) alkylidene group or replacement or unsubstituted (C3-C30) thiazolinyl to be connected to form alicyclic ring or monocycle or many cyclophanes ring with adjacent substituting group, the carbon atom of wherein said alicyclic ring or monocycle or many cyclophanes ring can be by one or more nitrogen that are selected from, the heteroatoms of oxygen and sulphur replaces;
Ar represents hydrogen independently, deuterium, halogen, has or do not have substituent (C1-C30) alkyl, has or do not have substituent (C6-C30) aryl, have or do not have substituent (C3-C30) Cycloalkylfused replacement or unsubstituted (C6-C30) aryl with one or more, has or do not have substituent (C3-C30) heteroaryl, have or do not have substituent 5 yuan to 7 yuan Heterocyclylalkyls, with one or more 5 yuan to 7 yuan Heterocyclylalkyls that have or do not have substituent aromatic ring to condense, has or do not have substituent (C3-C30) cycloalkyl, with one or more (C3-C30) cycloalkyl that have or do not have substituent aromatic ring to condense, cyano group, nitro, hydroxyl,-NR 21R 22,-BR 23R 24,-PR 25R 26,-P (=O) R 27R 28,-SiR 29R 30R 31,-YR 32, have or do not have substituent (C6-C30) aryl (C1-C30) alkyl, have or do not have substituent (C2-C30) thiazolinyl or have or do not have substituent (C2-C30) alkynyl;
A represents chemical bond, has or does not have substituent (C6-C30) arylidene, has or do not have substituent (C2-C30) inferior heteroaryl or has or do not have substituent (C6-C30) inferior arylthio (arylenethio);
B represents chemical bond, has or do not have substituent (C2-C30) alkylidene group, has or do not have substituent (C6-C30) arylidene, has or do not have substituent (C3-C30) inferior heteroaryl, have or do not have substituent 5 yuan to 7 yuan heterocycle alkylidene groups, with one or more 5 yuan to 7 yuan heterocycle alkylidene groups that have or do not have substituent aromatic ring to condense, has or do not have substituent (C3-C30) ring alkylidene group, with one or more (C3-C30) ring alkylidene groups that have or do not have substituent aromatic ring to condense, with one or more (C6-C30) arylidene that have or do not have substituent alicyclic ring to condense, has or do not have substituent (C2-C30) alkenylene, has or do not have substituent (C2-C30) alkynylene, has or do not have substituent (C6-C30) aryl (C1-C30) alkylidene group, has or do not have substituent (C 1-C30) alkylene sulfenyl (alkylenethio), has or do not have substituent (C1-C30) alkylene oxide group, have or do not have substituent (C6-C30) inferior aryloxy or have or do not have substituent (C6-C30) inferior arylthio (arylenethio);
R 21To R 32Represent independently hydrogen, has or do not have substituent (C1-C30) alkyl, has or do not have substituent (C6-C30) aryl, has or do not have substituent (C3-C30) heteroaryl, have or do not have substituent (C3-C30) cycloalkyl or have or do not have substituent (C3-C30) Heterocyclylalkyl, perhaps each in them can by with or do not have the replacement of condensed ring or unsubstituted (C3-C30) alkylidene group or replacement or unsubstituted (C3-C30) alkenylene to be connected to form alicyclic ring or monocycle or many cyclophanes ring with adjacent substituting group;
Y represents S or O;
A and b represent 1 to 3 integer independently;
When a more than or equal to 2 the time, each A can be identical or different, when b more than or equal to 2 the time, each B can be identical or different, adjacent substituting group can interconnect to form ring; And
Described Heterocyclylalkyl or heteroaryl comprise one or more B of being selected from, N, O, S, P (=O), the heteroatoms of Si and P.
In the present invention, " alkyl ", " alkoxyl group " and other substituting groups that comprises " alkyl " part comprise straight chain and a chain portion.In the present invention, cycloalkyl comprises the polynuclear hydrocarbon ring, as has or do not have substituent adamantyl or have or do not have substituent (C7-C30) bicyclic alkyl and monocyclic hydrocarbon ring.
In the present invention, " aryl " represent by remove the organic group that a hydrogen atom obtains from aromatic hydrocarbons, can comprise 4 yuan to 7 yuan, particularly monocycle or the condensed ring of 5 yuan or 6 yuan, comprises by singly linked a plurality of aryl.Object lesson comprises, but be not limited to, phenyl, naphthyl, xenyl (biphenyl), anthryl, indenyl, fluorenyl, phenanthryl (phenanthryl), benzo [9,10] phenanthryl (triphenylenyl), pyrenyl, perylene base (perylenyl), base (chrysenyl), naphthacenyl (naphthacenyl), fluoranthene base (fluoranthenyl) etc.Naphthyl comprises 1-naphthyl and 2-naphthyl.Anthryl comprises 1-anthryl, 2-anthryl and 9-anthryl, and fluorenyl comprises 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.In the present invention, " heteroaryl " expression comprise 1 to 4 be selected from B, N, O, S, P (=O), the heteroatoms of Si and P is the aromatic yl group of carbon as aromatic ring frame atom, other aromatic ring frame atoms.It can be 5 yuan of obtaining with the phenyl ring condensation or 6 yuan of bicyclic heteroaryls or polyheteroaromatic, but and fractional saturation.Described heteroaryl also is included in the heteroaryl groups that has singly-bound between it.
Heteroaryl comprises the divalent aryl group, and wherein the heteroatoms in the ring can be oxidized or quaternized, to form for example N-oxide compound or quaternary ammonium salt.Concrete example comprises bicyclic heteroaryl such as furyl, thienyl, pyrryl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl group, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazine base, triazolyl, tetrazyl, furazan base (furazanyl), pyridyl, pyrazinyl, pyrimidyl, pyridazinyl etc.; Polyheteroaromatic is benzofuryl (benzofuranyl) for example, benzothienyl, isobenzofuran-base, benzimidazolyl-, benzothiazolyl, the benzisothiazole base, benzoisoxazole base benzoxazolyl, pseudoindoyl, indyl, indazolyl, the diazosulfide base, quinolyl, isoquinolyl, cinnolines base (cinnolinyl), quinazolyl, quinoxalinyl (quinoxalinyl), carbazyl, phenanthridinyl (phenanthridinyl), benzo dioxolyl (benzodioxolyl) etc.; And N-oxide compound (such as pyridyl N-oxide compound, quinolyl N-oxide compound etc.); And quaternary ammonium salt etc., but be not limited to this.
" (C1-C30) alkyl " as herein described can comprise (C1-C20) alkyl or (C1-C10) alkyl, and " (C6-C30) aryl " comprises (C6-C20) aryl or (C6-C12) aryl." (C3-C30) heteroaryl " group comprises (C3-C20) heteroaryl or (C3-C12) heteroaryl, and " (C3-C30) cycloalkyl " group comprises (C3-C20) cycloalkyl or (C3-C7) cycloalkyl." (C2-C30) alkenyl or alkynyl " group comprises (C2-C20) alkenyl or alkynyl, (C2-C10) alkenyl or alkynyl.
In term as herein described " replace or unsubstituted substituting group or have or do not have substituting group ", the unsubstituted substituting group of term " replacement " expression further is substituted base and replaces.R 1To R 2, R 3To R 11, R 12To R 19, Ar, A, B and R 21To R 32Substituting group can selectedly further replace from following one or more substituting groups: deuterium, halogen, has or do not have (C1-C30) alkyl of halogenic substituent, (C6-C30) aryl, has or do not have (C3-C30) heteroaryl of (C6-C30) aryl substituent, 5 yuan to 7 yuan Heterocyclylalkyls, 5 yuan to 7 yuan Heterocyclylalkyls that condense with one or more aromatic rings, (C3-C30) cycloalkyl, (C6-C30) cycloalkyl that condenses with one or more aromatic rings, R aR bR cSi-, (C2-C30) thiazolinyl, (C2-C30) alkynyl, cyano group, carbazyl ,-NR dR e,-BR fR g,-pR hR i,-P (=O) R jR k, (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, R 1X-, R mC (=O)-, R mC (=O) O-, carboxyl, nitro and hydroxyl; R wherein aTo R 1Independently expression (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl; X represents S or O; And R mExpression (C1-C30) alkyl, (C1-C30) alkoxyl group, (C6-C30) aryl or (C6-C30) aryloxy.
A represents chemical bond, has or does not have substituent (C6-C30) arylidene, has or do not have substituent (C2-C30) inferior heteroaryl or has or do not have substituent (C6-C30) inferior arylthio; B represents chemical bond, has or do not have substituent (C6-C30) arylidene, has or do not have substituent (C3-C30) inferior heteroaryl, with one or more 5 yuan to 7 yuan heterocycle alkylidene groups that have or do not have substituent aromatic ring to condense, with one or more (C3-C30) ring alkylidene groups that have or do not have substituent aromatic ring to condense, with one or more (C6-C30) arylidene that have or do not have substituent alicyclic ring to condense, have or do not have substituent (C2-C30) alkenylene or have or do not have substituent (C2-C30) alkynylene; R1 to R19 represents independently hydrogen, has or does not have substituent (C1-C30) alkyl, has or do not have substituent (C6-C30) aryl, has or do not have substituent (C3-C30) heteroaryl or NR 21R 22, or they each can by the C5 alkylidene group or
Figure BDA00002415256500071
Be connected to form ring with adjacent substituting group.
Similarly, Ar represents hydrogen, deuterium, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, the 2-ethylhexyl, trifluoromethyl, the perfluor ethyl, trifluoroethyl, perfluoro propyl, perfluoro butyl, fluorine, trimethyl silyl, triethylsilyl, the tripropyl silyl, the tri-tert silyl, t-butyldimethylsilyl, the 3,5-dimethylphenyl silyl, the triphenyl silyl, methoxyl group, oxyethyl group, positive propoxy, isopropoxy, n-butoxy, isobutoxy, tert.-butoxy, n-pentyloxy, isopentyloxy, positive hexyloxy, positive heptan the oxygen base, pyrryl, furyl, thiophenyl, imidazolyl, benzimidazolyl-, tetrazyl, pyrazinyl, pyrimidyl, benzofuryl, the benzo thiophenyl, pyrazolyl, indyl oxazolyl, benzothiazolyl benzoxazolyl, dimethylamino, diphenylamino, single methylamino-, (4-tert-butyl-phenyl) (phenyl) amino, single phenyl amino, phenoxy group, thiophenyl, trityl group, phenyl, naphthyl, xenyl, phenanthryl, pyrenyl, fluoranthene base (fluoranthenyl), pyridyl, indenyl, benzo [9,10] phenanthryl (triphenylenyl), tetralyl, 7H-benzo [c] fluorenyl, 7H-benzo [de] anthryl, tetrahydric quinoline group, anthryl, 7H-benzo [c] carbazyl, ethynyl, vinyl, quinolyl;
Figure BDA00002415256500081
Wherein W and Z represent independently chemical bond ,-(CR 61R 62) m-,-N (R 63)-,-S-,-O-,-Si (R 64) (R 65)-or-P (R 66)-, prerequisite is that they are not chemical bond simultaneously; R 41To R 54And R 61To R 66Represent independently hydrogen, deuterium, (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl or (C3-C30) cycloalkyl, perhaps they each by with or do not have the replacement of condensed ring or unsubstituted (C3-C30) alkylidene group or replacement or unsubstituted (C3-C30) alkenylene to be connected to form alicyclic ring or monocycle or many cyclophanes ring with adjacent substituting group; M represents 1 to 3 integer; Ar can also be selected from one or more substituting groups of lower group and further be replaced: deuterium, methyl, the tertiary butyl, fluorine, methoxyl group, phenyl, triphenyl silyl, carbazyl, 1-phenyl-1H-benzo [d] imidazoles-2-base, benzo [d] thiazol-2-yl, naphthyl, diphenylamino, phenylcarbonyl group, (4-tert-butyl-phenyl) (phenyl) amino, trityl group, (diphenyl amino) phenyl and dibenzothiophene base.
More specifically, A is selected from chemical bond or following structure:
Figure BDA00002415256500082
, and
Figure BDA00002415256500083
Can be selected from following structure:
Organic electroluminescent compounds is selected from lower group of compound, but the invention is not restricted to described compound.
Figure BDA00002415256500101
Figure BDA00002415256500111
Figure BDA00002415256500131
Organic electroluminescent compounds of the present invention can be prepared shown in following scheme 1.
Scheme 1
Wherein
R 1To R 2, R 3To R 11, R 12To R 19, A, B, Ar, a be identical with the definition in the Chemical formula 1 with b.
A kind of organic electroluminescence device is provided, and it comprises the first electrode; The second electrode; Insert one or more layers organic layer between described the first electrode and the second electrode, described organic layer comprises one or more organic electroluminescent compounds that Chemical formula 1 represents.Organic layer comprises electroluminescence layer, and wherein the organic electroluminescent compounds of Chemical formula 1 is as matrix or dopant material.
When the organic electroluminescent compounds of Chemical formula 1 is used as matrix, one or more doping agents have been comprised.The doping agent that is used for organic electroluminescence device of the present invention is not particularly limited, but can be selected from the compound that Chemical formula 2 represents:
Chemical formula 2
Figure BDA00002415256500141
Wherein
Ar 101And Ar 102Expression has or does not have substituent (C1-C30) alkyl independently, has or do not have substituent (C6-C30) aryl, has or do not have substituent (C4-C30) heteroaryl, have or do not have substituent (C6-C30) virtue amino, (C1-C30) alkylamino, have or do not have substituent 5 yuan to 7 yuan Heterocyclylalkyls, with one or more 5 yuan to 7 yuan Heterocyclylalkyls that have or do not have substituent aromatic ring to condense, have or do not have substituent (C3-C30) cycloalkyl or with one or more (C3-C30) cycloalkyl that have or do not have substituent aromatic ring to condense, perhaps Ar 101And Ar 102In each can by with or do not have (C3-C30) alkylidene group of condensed ring or (C3-C30) alkenylene connect to form alicyclic ring or monocycle or many cyclophanes ring;
When c is 1, Ar 103Expression has or does not have substituent (C6-C30) aryl, has or do not have substituent (C4-C30) heteroaryl or is selected from the substituting group of following structure;
Figure BDA00002415256500142
When c is 2, Ar 103Expression has or does not have substituent (C6-C30) arylidene, has or do not have substituent (C4-C30) inferior heteroaryl or is selected from the substituting group of following structure;
Figure BDA00002415256500143
Ar 104And Ar 105Expression has or does not have substituent (C6-C30) arylidene or has or do not have substituent (C4-C30) inferior heteroaryl independently;
R 101To R 103Represent independently hydrogen, deuterium, have or do not have substituent (C1-C30) alkyl, have or do not have substituent (C6-C30) aryl, have or do not have substituent (C5-C30) heteroaryl ,-NR 111R 112,-BR 113R 114,-PR 115R 116,-P (=O) R 117R 118,-SiR 119R 120R 121Perhaps-YR 122
R 111To R 122Represent independently hydrogen, have or do not have substituent (C1-C30) alkyl, have or do not have substituent (C6-C30) aryl, have or do not have substituent (C3-C30) heteroaryl, have or do not have substituent (C3-C30) cycloalkyl or have or do not have substituent (C3-C30) Heterocyclylalkyl, perhaps R 111To R 122Each can be connected with adjacent substituting group to form and have or do not have substituent (C3-C30) alicyclic ring, have or do not have substituent (C5-C30) heterolipid ring, have or do not have substituent (C6-C30) aromatic ring or have or do not have substituent (C6-C30) hetero-aromatic ring;
Y represents S or O;
D represents 1 to 4 integer; And
E represents 0 or 1 integer.
The dopant compound of Chemical formula 2 can represent with the compound with following structure, but be not limited to this:
Figure BDA00002415256500151
Figure BDA00002415256500171
When the organic electroluminescent compounds of Chemical formula 1 is used as doping agent in electroluminescence layer, comprised one or more matrix.The matrix that is used for organic electroluminescence device of the present invention is not particularly limited, but can be selected from the compound of chemical formula 3 to 4 expressions:
Chemical formula 3
(Ar 11) f-L 11-(Ar 12) g
Chemical formula 4
(Ar 13) h-L 12-(Ar 14) i
Wherein
L 11Expression has or does not have substituent (C6-C60) arylidene or has or do not have substituent (C4-C60) inferior heteroaryl;
L 12Expression has or does not have substituent anthrylene;
Ar 11To Ar 14Represent independently hydrogen, deuterium, halogen, has or do not have substituent (C1-C30) alkyl, has or do not have substituent (C6-C30) aryl, has or do not have substituent (C3-C30) heteroaryl, has or do not have substituent (C3-C30) cycloalkyl, have or do not have substituent (C3-C30) Cycloalkylfused replacement or unsubstituted (C6-C30) aryl with one or more, have or do not have substituent 5 yuan to 7 yuan Heterocyclylalkyls, with one or more 5 yuan to 7 yuan Heterocyclylalkyls that have or do not have substituent aromatic ring to condense, cyano group, nitro,-NR 201R 202,-BR 203R 204,-PR 205R 206,-P (=O) R 207R 208, R 209R 210R 211Si-, R 212X-, have or do not have substituent (C6-C30) aryl (C1-C30) alkyl, have or do not have substituent (C2-C30) thiazolinyl, have or do not have substituent (C2-C30) alkynyl, perhaps they each can by with or do not have the replacement of condensed ring or unsubstituted (C3-C30) alkylidene group or replacement or unsubstituted (C3-C30) alkenylene to be connected to form alicyclic ring or monocycle or many cyclophanes ring with adjacent substituting group, the carbon atom on wherein said alicyclic ring or monocycle or the many cyclophanes ring can be replaced by nitrogen;
R 201To R 212Expression has or does not have substituent (C1-C30) alkyl, has or do not have substituent (C6-C30) aryl or has or do not have substituent (C3-C30) heteroaryl independently;
X represents S or O;
Heterocyclylalkyl and heteroaryl comprise one or more B of being selected from, N, O, S, P (=O), the heteroatoms of Si and P;
F, g, h and i represent 0 to 4 integer independently.
The matrix compounds of chemical formula 3 to 4 can represent with the compound with following structure, but be not limited to this:
Figure BDA00002415256500181
Figure BDA00002415256500191
In organic electronic devices of the present invention, except the organic electroluminescent compounds that Chemical formula 1 represents, described organic layer can comprise simultaneously that also one or more are selected from the compound of aromatic amine compound and styryl aromatic amine compound.The example of described aromatic amine compound or styryl aromatic amine compound is referring to korean patent application 10-2008-0123276,10-2008-0107606 or 10-2008-0118428 number, but is not limited to this.
In addition, in organic electroluminescence device of the present invention, except the organic electroluminescent compounds that Chemical formula 1 represents, described organic layer can comprise that also one or more are selected from metal or the coordination compound of the organo-metallic of the periodic table of elements the 1st family, the 2nd family, period 4 and period 5 transition metal, lanthanide series metal and d-transition element.Described organic layer can comprise electroluminescence layer and charge generation layer.
In addition, except the organic electroluminescent compounds that described Chemical formula 1 represents, described organic layer also can comprise the organic electro luminescent layer of one or more emission blue light, green glow or ruddiness simultaneously, to realize that emission is from the organic electroluminescence device of light.The example of the compound of blue light-emitting, green glow or ruddiness can be korean patent application 10-2008-0123276,10-2008-0107606 or 10-2008-0118428 number described compound, but is not limited to this.
In organic electroluminescence device of the present invention, the layer (hereinafter referred to as " upper layer ") that is selected from chalcogenide layer, metal halide and metal oxide layer can be arranged on the internal surface of one or two electrode in the electrode pair.More particularly, the metal chalcogenide of silicon or aluminium (comprising oxide compound) layer can place on the anode surface of electroluminescent medium layer, and metal halide or metal oxide layer can place on the cathode surface of described electroluminescent medium layer.Thereby obtain job stability.
For example, chalkogenide can be SiO x(1≤x≤2), AlO x(1≤x≤1.5), SiON, SiAlON etc.For example, metal halide can be LiF, MgF 2, CaF 2, rare earth metal fluorochemical etc.For example, metal oxide can be Cs 2O, Li 2O, MgO, SrO, BaO, CaO etc.
In organic electroluminescence device of the present invention, the mixing zone of electron transport compound and reductibility doping agent also preferably is set at least one surface of prepared electrode pair, perhaps the hole transports the mixing zone of compound and oxidisability doping agent.In this case, because the electron transport compound is reduced into negatively charged ion, thereby promotes electronics from the mixing zone injection and be transported to electroluminescent medium.In addition, form positively charged ion because the hole transports compound oxidation, thereby promote the hole from the mixing zone injection and be transported to electroluminescent medium.Preferred oxidisability doping agent comprises various Lewis acids and acceptor compound.Preferred reductibility doping agent comprises basic metal, alkali metal compound, alkaline-earth metal, rare earth metal and composition thereof.In addition, the electroluminescent device that emits white light that has two-layer or a more multi-layered electroluminescence layer can make as charge generation layer with the reductibility dopant layer.
The beneficial effect of the invention
Because organic electroluminescent compounds of the present invention has good luminous efficiency and good life properties, it can be used for making the OLED device with very excellent working life.
The embodiment of invention
The below with regard to organic electroluminescent compounds of the present invention, prepare the technique of this compound and use the aspect of Electroluminescence Properties of the device of this compound to further describe the present invention.But, for the purpose of setting forth, providing following examples, these embodiment limit the scope of the invention.
[preparation example 1] preparation compound 1
Figure BDA00002415256500211
The preparation of compound 1-1
Be dissolved in Anaesthetie Ether (1000mL) afterwards at 7H-benzo [de] anthracene-7-ketone (40.0g, 0.17mol), to wherein slowly adding AlCl 3(28g, 0.21mol).After stirring the mixture 15 minutes, mixture is cooled to 0 ℃ and to wherein slowly adding lithium aluminum hydride (LAH) (10g, 0.26mol).After the lower stirring of mixture backflow 1 hour, so that mixture Slow cooling after reaction is finished arrives room temperature.In mixture, slowly add EA until bubbling stops.Adding 6M HCl (100mL) afterwards, with distilled water and ethyl acetate mixture is extracted.Use MgSO 4Dry organic layer uses methylene dichloride and hexane to obtain compound 1-1 (36.0g, 95%) as eluent by the column chromatography purifying also with after the rotary-type vaporizer desolventizing.
The preparation of compound 1-2
Be dissolved in DMSO (420mL) afterwards at compound 1-1 (36.0g, 0.16mol), add at room temperature that the trimethyl carbinol is received (113.0g, 1.2mol) and stirred 15 minutes at 70 ℃.To wherein slowly adding methyl-iodide (90mL, 1.4mol) afterwards, stirred 1 hour.After reaction is finished, with the reaction mixture cool to room temperature, and to wherein adding distilled water.After mixture is stirred 20 minutes, make solid and filtration.Obtain compound 1-2 (26g, 63%) by with methyl alcohol and acetone solid being carried out recrystallization.
The preparation of compound 1-3
Compound 1-2 (20g, 90mmol) is dissolved among the DMF (300mL), and to wherein slowly adding N-bromosuccinimide (16g, 90mmol).Mixture was at room temperature stirred 1 day.After reaction is finished, extract mixture with distilled water and EA.Use MgSO 4Dry organic layer uses methylene dichloride and hexane to obtain target compound 1-3 (26g, 91%) as eluent by the column chromatography purifying also with after the rotary-type vaporizer desolventizing.
The preparation of compound 1
With 10-phenylanthracene-9-ylboronic acid (32g, 107mmol), compound 1-3 (25g, 82mmol), Pd (PPh 3) 4(6.2g, 5.4mmol) and Na 2CO 3(17.4g, 164mmol) is dissolved in toluene/ethanol/distilled water of 400mL/100mL/80mL, 100 ℃ of stirrings.After reaction is finished, extract mixture with distilled water and EA.Use MgSO 4Dry organic layer uses methylene dichloride and hexane to obtain target compound 1 (3g, 81%) as eluent by the column chromatography purifying also with after the rotary-type vaporizer desolventizing.
[preparation example 2] preparation compound 57
Figure BDA00002415256500221
With 4-(10-phenylanthracene-9-yl) phenyl-boron dihydroxide (40g, 107mmol), compound 1-3 (25g, 82mmol), Pd (PPh 3) 4(6.2g, 5.4mmol) and Na 2CO 3(17.4g, 164mmol) is dissolved in toluene/ethanol/distilled water of 400mL/100mL/80mL, 100 ℃ of stirrings.After reaction is finished, extract mixture with distilled water and EA.Use MgSO 4Dry organic layer uses methylene dichloride and hexane to obtain target compound 57 (37g, 79%) as eluent by the column chromatography purifying also with after the rotary-type vaporizer desolventizing.
Method according to preparation example 1 and 2 is prepared with organic electro luminescent compounds 1 to 73.The organic electroluminescent compounds that makes like this 1H NMR and MS/FAB data rows are in table 1.
Table 1
Figure BDA00002415256500222
Figure BDA00002415256500231
Figure BDA00002415256500241
Figure BDA00002415256500251
Figure BDA00002415256500261
Figure BDA00002415256500271
Figure BDA00002415256500281
Figure BDA00002415256500291
Figure BDA00002415256500301
[embodiment 1] uses organic electroluminescent compounds of the present invention to prepare the OLED device
Use electroluminescent material of the present invention to make the OLED device.At first, (15 Ω/) (available from SCP company (Samsung-Corning)) carry out ultrasonic cleaning with trieline, acetone, ethanol and distilled water to the transparency electrode ito thin film that is used for OLED successively that will be made by glass, and are stored in the Virahol before use.
Then, the ITO substrate is contained in the substrate folder (folder) of vacuum phase deposition equipment, with 4,4 ', 4 " three (N, N-(2-naphthyl)-phenyl amino) triphenylamine (2-TNATA) places the cell (cell) of vacuum phase deposition equipment, then; exhaust, makes indoor vacuum tightness be up to 10 -6Holder.Then, by applying electric current to described cell with evaporation 2-TNATA, form the thick hole injection layer of 60nm at the ITO substrate.Then, in another cell of vacuum sediment equipment, put into N, N '-two (Alpha-Naphthyl)-N, N '-phenylbenzene-4,4 '-diamines (NPB), apply electric current evaporation NPB to described cell, thereby at the thick hole transport layer of described hole injection layer deposition 20nm.
After forming hole injection layer and hole transport layer, form in the above electroluminescence layer, specific as follows.Compound 1 is placed in the cell of vacuum phase deposition equipment as matrix, Compound D is placed in another chamber as doping agent.With different speed evaporation bi-material, like this with 2 to 5 % by weight by being entrained in the thick electroluminescence layer of vapour deposition 30nm on the hole transport layer.
Figure BDA00002415256500311
Compound D
Afterwards, three (oxine)-aluminium (III) that vapour deposition 20nm is thick on electroluminescence layer are (Alq) as electron transport layer.Then, the oxine lithium (lithiumquinolate, Liq) of the following structure that vapour deposition 1 to 2nm is thick as electron injecting layer after, use another vacuum sediment equipment to form the thick Al negative electrode of 150nm, to make OLED.
The every kind of compound that is used for OLED passes through 10 -6Purifying is carried out in vacuum-sublimation under the condition of holder.
As a result, current flowing is 7.4mA/cm under the voltage of confirmation 7.0V 2, launched 1085cd/m 2Blue light.
[embodiment 2]
Make as described in Example 1 the OLED device, difference is to add compound 4 as substrate material at electroluminescence layer.
As a result, current flowing is 8.0mA/cm under the voltage of confirmation 7.2V 2, launched 1090cd/m 2Blue light.
[embodiment 3]
Make as described in Example 1 the OLED device, difference is to add compound 5 as substrate material at electroluminescence layer.
As a result, current flowing is 8.1mA/cm under the voltage of confirmation 7.4V 2, launched 1020cd/m 2Blue light.
[embodiment 4]
Prepare as described in Example 1 the OLED device, difference is to add compound 14 as substrate material at electroluminescence layer.
As a result, current flowing is 8.4mA/cm under the voltage of confirmation 7.8V 2, launched 1060cd/m 2Blue light.
[embodiment 5]
Prepare as described in Example 1 the OLED device, difference is to add compound 58 as substrate material at electroluminescence layer.
As a result, current flowing is 7.9mA/cm under the voltage of confirmation 7.2V 2, launched 1120cd/m 2Blue light.
[embodiment 6]
Prepare as described in Example 1 the OLED device, difference is to add compound 59 as substrate material at electroluminescence layer, N 9, N 9, N 10, N 10, 2,6-hexaphenyl anthracene-9,10-diamines (compd E) is as the electroluminescent doping agent.
Figure BDA00002415256500321
Compound (E)
As a result, current flowing is 8.2mA/cm under the voltage of confirmation 7.2V 2, launched 1480cd/m 2Green glow.
[embodiment 7]
Prepare as described in Example 6 the OLED device, difference is to add compound 53 as substrate material at electroluminescence layer.
As a result, current flowing is 8.9mA/cm under the voltage of confirmation 7.0V 2, launched 1570cd/m 2Green glow.
[embodiment 8]
Prepare as described in Example 6 the OLED device, difference is to add compound 45 as substrate material at electroluminescence layer.
As a result, current flowing is 8.5mA/cm under the voltage of confirmation 6.8V 2, launched 1500cd/m 2Green glow.
[embodiment 9]
Prepare as described in Example 6 the OLED device, difference is to add compound 62 as substrate material at electroluminescence layer.
As a result, current flowing is 8.7mA/cm under the voltage of confirmation 7.0V 2, launched 1610cd/m 2Green glow.
[embodiment 10]
Prepare as described in Example 1 the OLED device, difference is to add dinaphthyl anthracene (DNA) as substrate material at electroluminescence layer, and compound 69 is as doping agent.
As a result, current flowing is 8.6mA/cm under the voltage of 7.2V 2, launched 1530cd/m 2Green glow.
[embodiment 11]
Prepare as described in Example 1 the OLED device, difference is to add dinaphthyl anthracene (DNA) as substrate material at electroluminescence layer, and compound 68 is as doping agent.
As a result, current flowing is 8.7mA/cm under the voltage of confirmation 7.4V 2, launched 1590cd/m 2Green glow.
[embodiment 12]
Prepare as described in Example 1 the OLED device, difference is to add dinaphthyl anthracene (DNA) as substrate material at electroluminescence layer, and compound 73 is as doping agent.
As a result, current flowing is 8.6mA/cm under the voltage of confirmation 7.4V 2, launched 1500cd/m 2Green glow.
[comparative example 1]
Same way as prepares OLED as described in Example 1, and difference is to use in a cell of vacuum phase deposition equipment dinaphthyl anthracene (DNA) to replace compound of the present invention as substrate material, uses Compound D as doping agent.
As a result, current flowing is 11.0mA/cm under the voltage of confirmation 6.7V 2, launched 1320cd/m 2Blue light.
[comparative example 2]
Same way as prepares OLED as described in Example 1, and difference is to use in a cell of vacuum phase deposition equipment dinaphthyl anthracene (DNA) to replace compound of the present invention as substrate material, uses N 9, N 9, N 10, N 10, 2,6-hexaphenyl anthracene-9,10-diamines (compd E) is as doping agent.
As a result, current flowing is 11.0mA/cm under the voltage of confirmation 7.2V 2, launched 1793cd/m 2Blue light.
As mentioned above, than common used material, organic electroluminescent compounds of the present invention has been realized higher efficient and purity of color.May be because the resonance of dimethylbenzanthracene has good purity of color.Because steric hindrance has caused compound 5 to have the characteristic that demonstrates better luminous efficiency.By introduce phenyl between substituting group, compound 58 has significant advantage aspect watt consumption and the working life.Than comparative example 2, in the situation of compound 62, can increase resonant length by introducing the phenyl that connects in the 2-position of anthracene, to increase the working life of green organic electroluminescent compounds.Therefore, should understand organic electroluminescent compounds of the present invention can be as having high-level efficiency and long-life electroluminescent material.
Industrial usability
Because organic electroluminescent compounds of the present invention has good luminous efficiency and good life properties, it can be used for making the OLED device with very excellent working life.

Claims (11)

1. organic electroluminescent compounds that is represented by Chemical formula 1:
Chemical formula 1
Figure FDA00002415256400011
Wherein
R 1To R 2Represent independently hydrogen, deuterium, halogen, have or do not have substituent (C1-C30) alkyl, have or do not have substituent (C6-C30) aryl, have or do not have substituent (C3-C30) heteroaryl or have or do not have substituent five yuan to the seven membered heterocyclic alkyl;
R 3To R 11Represent independently hydrogen, deuterium, halogen, have or do not have substituent (C1-C30) alkyl, have or do not have substituent (C6-C30) aryl, have or do not have substituent (C3-C30) heteroaryl, have or do not have substituent five yuan to seven membered heterocyclic alkyl, cyano group, nitro, hydroxyl ,-NR 21R 22,-BR 23R 24,-PR 25R 26,-P (=O) R 27R 28,-SiR 29R 30R 31Perhaps-YR 32
R 12To R 19Represent independently hydrogen, deuterium, halogen, has or do not have substituent (C1-C30) alkyl, has or do not have substituent (C6-C30) aryl, have or do not have substituent (C3-C30) Cycloalkylfused replacement or unsubstituted (C6-C30) aryl with one or more, has or do not have substituent (C3-C30) heteroaryl, has or do not have the first Heterocyclylalkyl of substituent 5-to 7-, with one or more 5-to 7-unit Heterocyclylalkyls that have or do not have substituent aromatic ring to condense, has or do not have substituent (C3-C30) cycloalkyl, with one or more (C3-C30) cycloalkyl that have or do not have substituent aromatic ring to condense, cyano group, nitro, hydroxyl,-NR 21R 22,-BR 23R 24,-PR 25R 26,-P (=O) R 27R 28,-SiR 29R 30R 31,-YR 32Has or do not have substituent (C6-C30) aryl (C1-C30) alkyl, has or do not have substituent (C2-C30) thiazolinyl, has or do not have substituent (C2-C30) alkynyl, perhaps each in them can by with or do not have the replacement of condensed ring or unsubstituted (C3-C30) alkylidene group or replacement or unsubstituted (C3-C30) alkenylene to be connected to form alicyclic ring or monocycle or many cyclophanes ring with adjacent substituting group, the carbon atom of wherein said alicyclic ring or monocycle or many cyclophanes ring can be by one or more nitrogen that are selected from, the heteroatoms of oxygen and sulphur replaces;
Ar represents hydrogen independently, deuterium, halogen, has or do not have substituent (C1-C30) alkyl, has or do not have substituent (C6-C30) aryl, have or do not have substituent (C3-C30) Cycloalkylfused replacement or unsubstituted (C6-C30) aryl with one or more, has or do not have substituent (C3-C30) heteroaryl, have or do not have substituent 5 yuan to 7 yuan Heterocyclylalkyls, with one or more 5 yuan to 7 yuan Heterocyclylalkyls that have or do not have substituent aromatic ring to condense, has or do not have substituent (C3-C30) cycloalkyl, with one or more (C3-C30) cycloalkyl that have or do not have substituent aromatic ring to condense, cyano group, nitro, hydroxyl,-NR 21R 22,-BR 23R 24,-PR 25R 26,-P (=O) R 27R 28,-SiR 29R 30R 31,-YR 32, have or do not have substituent (C6-C30) aryl (C1-C30) alkyl, have or do not have substituent (C2-C30) thiazolinyl or have or do not have substituent (C2-C30) alkynyl;
A represents chemical bond, has or does not have substituent (C6-C30) arylidene, has or do not have substituent (C2-C30) heteroarylidene or has or do not have substituent (C6-C30) inferior arylthio;
B represents chemical bond, has or do not have substituent (C2-C30) alkylidene group, has or do not have substituent (C6-C30) arylidene, has or do not have substituent (C3-C30) heteroarylidene, have or do not have substituent 5 yuan to 7 yuan heterocycle alkylidene groups, with one or more 5 yuan to 7 yuan heterocycle alkylidene groups that have or do not have substituent aromatic ring to condense, has or do not have substituent (C3-C30) ring alkylidene group, with one or more (C3-C30) ring alkylidene groups that have or do not have substituent aromatic ring to condense, with one or more (C6-C30) arylidene that have or do not have substituent alicyclic ring to condense, has or do not have substituent (C2-C30) alkenylene, has or do not have substituent (C2-C30) alkynylene, has or do not have substituent (C6-C30) aryl (C1-C30) alkylidene group, has or do not have substituent (C1-C30) alkylene sulfenyl, has or do not have substituent (C1-C30) alkylene oxide group, have or do not have substituent (C6-C30) inferior aryloxy or have or do not have substituent (C6-C30) inferior arylthio;
R21 to R 32Represent independently hydrogen, has or do not have substituent (C1-C30) alkyl, has or do not have substituent (C6-C30) aryl, has or do not have substituent (C3-C30) heteroaryl, have or do not have substituent (C3-C30) cycloalkyl or have or do not have substituent (C3-C30) Heterocyclylalkyl, perhaps each in them can by with or do not have the replacement of condensed ring or unsubstituted (C3-C30) alkylidene group or replacement or unsubstituted (C3-C30) alkenylene to be connected to form alicyclic ring or monocycle or many cyclophanes ring with adjacent substituting group;
Y represents S or O;
A and b represent 1 complete 3 integer independently;
When a more than or equal to 2 the time, each A can be identical or different, when b more than or equal to 2 the time, each B can be identical or different, adjacent substituting group can interconnect to form ring; And
Described Heterocyclylalkyl or heteroaryl comprise one or more B of being selected from, N, O, S, P (=O), the heteroatoms of Si and P.
2. organic electroluminescent compounds as claimed in claim 1 is characterized in that, described R 1To R 2, R 3To R 11, R 12To R 19, Ar, A, B and R 21To R 32Substituting group can selectedly further replace from following one or more substituting groups: deuterium, halogen, has or do not have (C1-C30) alkyl of halogenic substituent, (C6-C30) aryl, has or do not have (C3-C30) heteroaryl of (C6-C30) aryl substituent, 5 yuan to 7 yuan Heterocyclylalkyls, 5 yuan to 7 yuan Heterocyclylalkyls that condense with one or more aromatic rings, (C3-C30) cycloalkyl, (C6-C30) cycloalkyl that condenses with one or more aromatic rings, R aR bR cSi-, (C2-C30) thiazolinyl, (C2-C30) alkynyl, cyano group, carbazyl ,-NR dR e,-BR fR g,-PR hR i,-P (=O) R jR k, (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, R 1X-, R mC (=O)-, R mC (=O) O-, carboxyl, nitro and hydroxyl; R wherein aTo R 1Independently expression (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl; X represents S or O; And R mExpression (C1-C30) alkyl, (C1-C30) alkoxyl group, (C6-C30) aryl or (C6-C30) aryloxy.
3. organic electroluminescent compounds as claimed in claim 1, it is characterized in that described A represents chemical bond, has or do not have substituent (C6-C30) arylidene, has or do not have substituent (C2-C30) heteroarylidene or has or do not have substituent (C6-C30) inferior arylthio; B represents chemical bond, has or do not have substituent (C6-C30) arylidene, has or do not have substituent (C3-C30) heteroarylidene, with one or more 5 yuan to 7 yuan heterocycle alkylidene groups that have or do not have substituent aromatic ring to condense, with one or more (C3-C30) ring alkylidene groups that have or do not have substituent aromatic ring to condense, with one or more (C6-C30) arylidene that have or do not have substituent alicyclic ring to condense, have or do not have substituent (C2-C30) alkenylene or have or do not have substituent (C2-C30) alkynylene; R 1To R 19Represent independently hydrogen, have or do not have substituent (C1-C30) alkyl, have or do not have substituent (C6-C30) aryl, have or do not have substituent (C3-C30) heteroaryl or-NR 21R 22, or they each can by the C5 alkylidene group or
Figure FDA00002415256400031
Be connected to form ring with adjacent substituting group.
4. organic electroluminescent compounds as claimed in claim 1, it is characterized in that, described Ar represents hydrogen, deuterium, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, the 2-ethylhexyl, trifluoromethyl, the perfluor ethyl, trifluoroethyl, perfluoro propyl, perfluoro butyl, fluorine, trimethyl silyl, triethylsilyl, the tripropyl silyl, the tri-tert silyl, t-butyldimethylsilyl, the 3,5-dimethylphenyl silyl, the triphenyl silyl, methoxyl group, oxyethyl group, positive propoxy, isopropoxy, n-butoxy, isobutoxy, tert.-butoxy, n-pentyloxy, isopentyloxy, positive hexyloxy, positive heptan the oxygen base, pyrryl, furyl, thiophenyl, imidazolyl, benzimidazolyl-, tetrazyl, pyrazinyl, pyrimidyl, benzofuryl, the benzo thiophenyl, pyrazolyl, indyl oxazolyl, benzothiazolyl benzoxazolyl, dimethylamino, diphenylamino, single methylamino-, (4-tert-butyl-phenyl) (phenyl) amino, single phenyl amino, phenoxy group, thiophenyl, trityl group, phenyl, naphthyl, xenyl, phenanthryl, pyrenyl, the fluoranthene base, pyridyl, indenyl, benzo [9,10] phenanthryl, tetralyl, 7H-benzo [c] fluorenyl, 7H-benzo [de] anthryl, tetrahydric quinoline group, anthryl, 7H-benzo [c] carbazyl, ethynyl, vinyl, quinolyl
Figure FDA00002415256400041
Wherein W and Z represent independently chemical bond ,-(CR 61R 62) m-,-N (R 63)-,-S-,-O-,-Si (R 64) (R 65)-or-P (R 66)-, prerequisite is that they are not chemical bond simultaneously; R 41To R 54And R 61To R 66Represent independently hydrogen, deuterium, (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl or (C3-C30) cycloalkyl, perhaps they each by with or do not have the replacement of condensed ring or unsubstituted (C3-C30) alkylidene group or replacement or unsubstituted (C3-C30) alkenylene to be connected to form alicyclic ring or monocycle or many cyclophanes ring with adjacent substituting group; M represents 1 to 3 integer; Ar can also be selected from one or more substituting groups of lower group and further be replaced: deuterium, methyl, the tertiary butyl, fluorine, methoxyl group, phenyl, triphenyl silyl, carbazyl, 1-phenyl-1H-benzo [d] imidazoles-2-base, benzo [d] thiazol-2-yl, naphthyl, diphenylamino, phenylcarbonyl group, (4-tert-butyl-phenyl) (phenyl) amino, trityl group, (diphenyl amino) phenyl and dibenzothiophene base.
5. organic electroluminescent compounds as claimed in claim 1 is characterized in that, A is selected from chemical bond or following structure:
Figure FDA00002415256400051
And
Figure FDA00002415256400052
Be selected from following structure:
Figure FDA00002415256400053
Figure FDA00002415256400061
6. organic electroluminescence device, described device comprises each described organic electroluminescent compounds in the claim 1 to 5.
7. organic electroluminescence device as claimed in claim 6 is characterized in that, this device comprises: the first electrode; The second electrode; And insert one or more layers organic layer between described the first electrode and the second electrode, wherein said organic layer comprises one or more such as each described organic electroluminescent compounds in the claim 1 to 5, and one or more doping agents of chemical formula (2) expression:
Chemical formula 2
Figure FDA00002415256400062
Wherein
Ar 101And Ar 102Expression has or does not have substituent (C1-C30) alkyl independently, has or do not have substituent (C6-C30) aryl, has or do not have substituent (C4-C30) heteroaryl, have or do not have substituent (C6-C30) virtue amino, (C1-C30) alkylamino, have or do not have substituent 5 yuan to 7 yuan Heterocyclylalkyls, with one or more 5 yuan to 7 yuan Heterocyclylalkyls that have or do not have substituent aromatic ring to condense, have or do not have substituent (C3-C30) cycloalkyl or with one or more (C3-C30) cycloalkyl that have or do not have substituent aromatic ring to condense, perhaps Ar 101And Ar 102In each can by with or do not have (C3-C30) alkylidene group of condensed ring or (C3-C30) alkenylene connect to form alicyclic ring or monocycle or many cyclophanes ring;
When c is 1, Ar 103Expression has or does not have substituent (C6-C30) aryl, has or do not have substituent (C4-C30) heteroaryl or is selected from the substituting group of following structure;
Figure FDA00002415256400071
When c is 2, Ar 103Expression has or does not have substituent (C6-C30) arylidene, has or do not have substituent (C4-C30) heteroarylidene or is selected from the substituting group of following structure;
Figure FDA00002415256400072
Ar 104And Ar 105Expression has or does not have substituent (C6-C30) arylidene or has or do not have substituent (C4-C30) heteroarylidene independently;
R 101To R 103Represent independently hydrogen, deuterium, have or do not have substituent (C1-C30) alkyl, have or do not have substituent (C6-C30) aryl, have or do not have substituent (C5-C30) heteroaryl ,-NR 111R 112,-BR 113R 114,-PR 115R 116,-P (=O) R 117R 118,-SiR 119R 120R 121Perhaps-YR 122
R 111To R 122Represent independently hydrogen, have or do not have substituent (C1-C30) alkyl, have or do not have substituent (C6-C30) aryl, have or do not have substituent (C3-C30) heteroaryl, have or do not have substituent (C3-C30) cycloalkyl or have or do not have substituent (C3-C30) Heterocyclylalkyl, perhaps R 111To R 122Each can be connected with adjacent substituting group to form and have or do not have substituent (C3-C30) alicyclic ring, have or do not have substituent (C5-C30) heterolipid ring, have or do not have substituent (C6-C30) aromatic ring or have or do not have substituent (C6-C30) hetero-aromatic ring;
Y represents S or O;
D represents 1 to 4 integer; And
E represents 0 or 1 integer.
8. organic electroluminescence device as claimed in claim 6 is characterized in that, this device comprises the first electrode; The second electrode; Insert one or more layers organic layer between described the first electrode and the second electrode, described organic layer includes one or more matrix compounds of organic electro luminescent compounds and chemical formula 3 or 4 expressions;
Chemical formula 3
(Ar 11) f-L 11-(Ar 12) g
Chemical formula 4
(Ar 13) h-L 12-(Ar 14) i
Wherein
L 11Expression has or does not have substituent (C6-C60) arylidene or has or do not have substituent (C4-C60) heteroarylidene;
L 12Expression has or does not have substituent anthrylene;
Ar 11To Ar 14Represent independently hydrogen, deuterium, halogen, has or do not have substituent (C1-C30) alkyl, has or do not have substituent (C6-C30) aryl, has or do not have substituent (C3-C30) heteroaryl, has or do not have substituent (C3-C30) cycloalkyl, have or do not have substituent (C3-C30) Cycloalkylfused replacement or unsubstituted (C6-C30) aryl with one or more, have or do not have substituent 5 yuan to 7 yuan Heterocyclylalkyls, with one or more 5 yuan to 7 yuan Heterocyclylalkyls that have or do not have substituent aromatic ring to condense, cyano group, nitro,-NR 201R 202,-BR 203R 204,-PR 205R 206,-P (=O) R 207R 208, R 209R 210R 211Si-, R 212X-, have or do not have substituent (C6-C30) aryl (C1-C30) alkyl, have or do not have substituent (C2-C30) thiazolinyl, have or do not have substituent (C2-C30) alkynyl, perhaps they each can by with or do not have the replacement of condensed ring or unsubstituted (C3-C30) alkylidene group or replacement or unsubstituted (C3-C30) alkenylene to be connected to form alicyclic ring or monocycle or many cyclophanes ring with adjacent substituting group, the carbon atom on wherein said alicyclic ring or monocycle or the many cyclophanes ring can be replaced by nitrogen;
R 201To R 212Expression has or does not have substituent (C1-C30) alkyl, has or do not have substituent (C6-C30) aryl or has or do not have substituent (C3-C30) heteroaryl independently;
X represents S or O;
Heterocyclylalkyl and heteroaryl comprise one or more B of being selected from, N, O, S, P (=O), the heteroatoms of Si and P;
F, g, h and i represent 0 to 4 integer independently.
9. organic electroluminescence device as claimed in claim 7, it is characterized in that, described organic layer also comprises one or more amine compound that is selected from aromatic amine compound and styryl aromatic amine compound, or one or more are selected from the metal of transition metal, lanthanide series metal and d-transition element of organo-metallic, period 4 and period 5 of the 1st family, the 2nd family of the periodic table of elements.
10. organic electroluminescence device as claimed in claim 7 is characterized in that, described organic layer comprises electroluminescence layer and charge generation layer.
11. organic electroluminescence device as claimed in claim 7 is characterized in that, this organic electroluminescence device is the organic electroluminescence device of transmitting white, and described organic layer also comprises the organic electro luminescent layer of one or more layers emission blue light, ruddiness or green glow.
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