CN103221406A - 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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CN103221406A
CN103221406A CN2011800555279A CN201180055527A CN103221406A CN 103221406 A CN103221406 A CN 103221406A CN 2011800555279 A CN2011800555279 A CN 2011800555279A CN 201180055527 A CN201180055527 A CN 201180055527A CN 103221406 A CN103221406 A CN 103221406A
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unsubstituted
replacement
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慎孝壬
黄守振
金希淑
尹石根
李美子
金南均
赵英俊
权赫柱
李暻周
金奉玉
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Rohm and Haas Electronic Materials Korea Ltd
Rohm and Haas Electronic Materials LLC
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Abstract

Provided are novel organic electroluminescent compounds and an organic electroluminescent device using the same. Because the organic electroluminescent compound disclosed herein exhibits good luminous efficiency and an excellent life performance, it may be used to manufacture OLED devices very superior in terms of operating life and which consume 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 present invention relates to novel organic electroluminescent compounds and the organic electroluminescence device that comprises this compound.
Technical background
In display device, the electroluminescent of self-emission display device (EL) device is preferred, because they provide wide visual angle, excellent contrast gradient and the speed of response fast.Eastman Kodak Co (Eastman Kodak) 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.
The greatest factor of the luminous efficiency of decision Organic Light Emitting Diode (OLED) is an electroluminescent material.Although up to the present fluorescent material has been widely used as electroluminescent material, from electroluminescent mechanism, the exploitation phosphor material is luminous efficiency to be improved to be up to one of preferred approach of 4 times in theory.Up to the present, iridium (III) complex compound is well-known a kind of phosphor material, comprises (acac) Ir (btp) 2, Ir (ppy) 3And Firpic, respectively as redness, green and blue phosphorescent material.Specifically, many phosphor materials are studied in Japan, Europe and the U.S. at present.
Figure BDA00003206670000011
At present, known CBP is the substrate material that is widely used as phosphor material most.Reported the efficient OLED that uses the hole blocking layer that comprises BCP, BAlq etc.Pioneer Electronic Corp. (Japan) etc. has reported and has used the high-performance OLED of BAlq derivative as matrix.
Figure BDA00003206670000012
Although these materials provide good electroluminescence characters,, may degrade in the high temperature deposition course of processing in a vacuum, thereby be disadvantageous because they have the thermostability of low second-order transition temperature and difference.Because the power efficiency of OLED is determined by (π/voltage) * current efficiency, so power efficiency and voltage are inversely proportional to.Need high power efficiency to reduce the watt consumption of OLED.In fact, use the OLED of phosphor material to provide than the much better current efficiency (cd/A) of OLED of using fluorescent material.But, when current material when for example BAlq, CBP etc. are as the matrix of phosphor material, to compare and use the OLED of fluorescent material not having clear superiority aspect the power efficiency (lm/W), this is because driving voltage is higher.In addition, use life-span of OLED device of this type of material also unsatisfactory.
On the other hand, international patent application has disclosed a kind of compound that is used for electroluminescent organic material for WO2006/049013 number, and its main chain has the fused bicyclic group.Yet, the not concrete compound that discloses of the document: use the carbazole main chain and the nitrogenous fused bicyclic group that replace with aromatic ring condensed cycloalkyl or Heterocyclylalkyl with following two kinds of features.
Summary of the invention
Technical problem
Therefore, the present invention notices the problem that correlation technique exists, and one object of the present invention is to provide the organic electroluminescent compounds with main chain, thereby can provide better luminous efficiency and the device lifetime with suitable chromaticity coordinates with respect to conventional material.
Another object of the present invention is to provide the organic electroluminescence device with high-level efficiency and long service live, and this luminescent device uses described organic electroluminescent compounds as electroluminescent material.
Technical scheme
A kind of compound that is used for the organic electroluminescent compounds that following Chemical formula 1 represents is provided, and the organic electroluminescence device that uses this compound.Because organic electroluminescent compounds of the present invention has superior luminous efficiency and excellent life properties, it can be used for making the OLED device, and this device has extremely superior working life and owing to improved power efficiency consumes less power.
Chemical formula 1
Figure BDA00003206670000031
Wherein:
Ring A represents monocycle or many cyclophanes ring;
X 1And X 2Represent N or CR ' independently;
L 1Expression singly-bound, replacement or unsubstituted (C6-C30) arylidene, replacement or unsubstituted (C2-C30) heteroarylidene or replacement or unsubstituted (C3-C30) ring alkylidene group;
Ar 1Expression hydrogen, deuterium, halogen, replacement or unsubstituted (C1-C30) alkyl, replacement or unsubstituted (C6-C30) aryl or replacement or unsubstituted (C2-C30) heteroaryl;
Z is independently selected from following structure:
And when described ring A was monocyclic aromatic rings, Z only was selected from following structure:
Figure BDA00003206670000033
Y represents-O-,-S-,-C (R 11R 12)-,-Si (R 13R 14)-or-N (R 15)-;
R 1To R 9Represent hydrogen independently, deuterium, halogen, replace or unsubstituted (C1-C30) alkyl, replace or unsubstituted (C6-C30) aryl, replace or unsubstituted (C2-C30) heteroaryl, replace or unsubstituted (C3-C30) cycloalkyl, replace or unsubstituted 5-to 7-unit Heterocyclylalkyl, replace or unsubstituted (C6-C30) aryl (C1-C30) alkyl, replacement or unsubstituted (C6-C30) aryl Cycloalkylfused with one or more (C3-C30), with replacement or the first Heterocyclylalkyl of unsubstituted one or more aromatic ring condensed 5-to 7-, with replacement or unsubstituted one or more aromatic ring condensed (C3-C30) cycloalkyl,-NR 16R 17,-SiR 18R 19R 20,-SR 21,-OR 22, cyano group, nitro or hydroxyl; Perhaps replacement that R1 to R9 can be by having or do not have condensed ring or unsubstituted (C3-C30) alkenylene or replacement or unsubstituted (C3-C30) alkylidene group link to each other with adjacent substituting group and form alicyclic ring and monocycle or many cyclophanes ring, and the carbon atom of this alicyclic ring and monocycle or many cyclophanes ring can be replaced by one or more heteroatomss that are selected from N, O and S;
R ' and R 11To R 22Represent hydrogen, deuterium, halogen, replacement or unsubstituted (C1-C30) alkyl, replacement or unsubstituted (C6-C30) aryl, replacement or unsubstituted (C2-C30) heteroaryl, replacement or unsubstituted 5-to 7-unit's Heterocyclylalkyl or replacement or unsubstituted (C3-C30) cycloalkyl independently; Perhaps replacement that they can be by having or do not have condensed ring or unsubstituted (C3-C30) alkenylene or replacement or unsubstituted (C3-C30) alkylidene group link to each other with adjacent substituting group and form alicyclic ring and monocycle or many cyclophanes ring, and the carbon atom of this alicyclic ring and monocycle or many cyclophanes ring can be replaced by one or more heteroatomss that are selected from N, O and S;
A, c, e and i represent 1 to 4 integer independently, and when a, c, e and I be during more than or equal to 2 integer, each R 1, R 3, R 5And R 9Can be identical or differ from one another;
B, d and g represent 1 to 3 integer independently, and when b, d and g be during more than or equal to 2 integer, each R 2, R 4And R 7Can be identical or differ from one another;
F represents 1 to 6 integer, and when f be during more than or equal to 2 integer, each R 6Can be identical or differ from one another;
H represents 1 to 5 integer, and when h be during more than or equal to 2 integer, each R 8Can be identical or differ from one another; And
Described hetero-aromatic ring, heteroarylidene, Heterocyclylalkyl and heteroaryl comprise one or more B of being selected from, N, O, S, P (=O), the heteroatoms of Si and P.
Term used herein " alkyl ", " alkoxyl group " and other substituting group that contains " alkyl " part comprise a straight chain and a chain portion, and " cycloalkyl " comprises polynuclear hydrocarbon ring (for example replacing or unsubstituted adamantyl or replacement or unsubstituted (C7-C30) bicyclic alkyl) and monocyclic hydrocarbon ring.Term used herein " aryl " refers to by removing the organic group that hydrogen atom obtains from aromatic hydrocarbon, and it can comprise the monocycle or the condensed ring of 4-to 7-unit, particularly 5-or 6-unit, even also comprises the structure by singly linked a plurality of aryl.Its object lesson includes but not limited to: phenyl, naphthyl, xenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, benzo [9,10] phenanthryl (triphenylenyl), pyrenyl, perylene base (perylenyl),
Figure BDA00003206670000041
Base (chrysenyl), naphthacenyl (naphthacenyl), fluoranthene base (fluoranthenyl) etc.Described naphthyl comprises 1-naphthyl and 2-naphthyl, described anthryl comprises 1-anthryl, 2-anthryl and 9-anthryl, described phenanthryl comprises 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl and 9-phenanthryl, and described naphthacenyl (naphthacenyl) comprises 1-naphthacenyl, 2-naphthacenyl and 9-naphthacenyl.Described pyrenyl comprises 1-pyrenyl, 2-pyrenyl and 4-pyrenyl, described xenyl comprises 2-xenyl, 3-xenyl and 4-xenyl, described terphenyl comprises right-terphenyl-4-base, right-terphenyl-the 3-base, right-terphenyl-the 2-base ,-terphenyl-4-base ,-terphenyl-3-base and-terphenyl-2-base, described fluorenyl comprises 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
Term used herein " heteroaryl " expression comprise 1-4 be selected from B, N, O, S, P (=O), the heteroatoms of Si and P is as the aromatic ring frame atom, and other aromatic ring frame atoms aromatic yl group that is carbon.It can be 5 yuan of obtaining with one or more phenyl ring condensations or 6 yuan of bicyclic heteroaryls or polyheteroaromatic, and can be fractional saturation.In the present invention, " heteroaryl " comprises the structure by singly linked one or more heteroaryls.Described heteroaryl comprises divalent aryl, and wherein the heteroatoms in the ring can be oxidized or quaternized, forms for example N-oxide compound or quaternary ammonium salt.Their concrete examples include, but are not limited to, and bicyclic heteroaryl is furyl, thienyl (thiophenyl), pyrryl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl group, isothiazolyl, isoxazolyl, oxazolyl, oxadiazole base, triazinyl, tetrazine base, triazolyl, furazan base (furazanyl), pyridyl, pyrazinyl, pyrimidyl, pyridazinyl etc. for example; Polyheteroaromatic is benzofuryl for example, benzothienyl, dibenzofuran group, the dibenzothiophene base, 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), acridyl, the phenanthroline base, phenazinyl, phenothiazinyl phenoxazinyl etc.; And N-oxide compound (for example pyridyl N-oxide compound, quinolyl N-oxide compound); Or its quaternary ammonium salt etc.
Pyrryl comprises: 1-pyrryl, 2-pyrryl and 3-pyrryl; Pyridyl comprises 2-pyridyl, 3-pyridyl and 4-pyridyl; Indyl comprises 1-indyl, 2-indyl, 3-indyl, 4-indyl, 5-indyl, 6-indyl and 7-indyl; Pseudoindoyl comprises 1-pseudoindoyl, 2-pseudoindoyl, 3-pseudoindoyl, 4-pseudoindoyl, 5-pseudoindoyl, 6-pseudoindoyl and 7-pseudoindoyl; Furyl comprises 2-furyl and 3-furyl; Benzofuryl comprises 2-benzofuryl, 3-benzofuryl, 4-benzofuryl, 5-benzofuryl, 6-benzofuryl and 7-benzofuryl; Isobenzofuran-base comprises 1-isobenzofuran-base, 3-isobenzofuran-base, 4-isobenzofuran-base, 5-isobenzofuran-base, 6-isobenzofuran-base and 7-isobenzofuran-base; Quinolyl comprises 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl and 8-quinolyl; Isoquinolyl comprises 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl and 8-isoquinolyl; Quinoxalinyl comprises 2-quinoxalinyl, 5-quinoxalinyl and 6-quinoxalinyl; Carbazyl comprises 1-carbazyl, 2-carbazyl, 3-carbazyl, 4-carbazyl and 9-carbazyl; Phenanthridinyl comprises 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl and 10-phenanthridinyl; Acridyl comprises 1-acridyl, 2-acridyl, 3-acridyl, 4-acridyl and 9-acridyl; The phenanthroline base comprises 1,7-phenanthroline-2-base, 1,7-phenanthroline-3-base, 1,7-phenanthroline-4-base, 1,7-phenanthroline-5-base, 1,7-phenanthroline-6-base, 1,7-phenanthroline-8-base, 1,7-phenanthroline-9-base, 1,7-phenanthroline-10-base, 1,8-phenanthroline-2-base, 1,8-phenanthroline-3-base, 1,8-phenanthroline-4-base, 1,8-phenanthroline-5-base, 1,8-phenanthroline-6-base, 1,8-phenanthroline-7-base, 1,8-phenanthroline-9-base, 1,8-phenanthroline-10-base, 1,9-phenanthroline-2-base, 1,9-phenanthroline-3-base, 1,9-phenanthroline-4-base, 1,9-phenanthroline-5-base, 1,9-phenanthroline-6-base, 1,9-phenanthroline-7-base, 1,9-phenanthroline-8-base, 1,9-phenanthroline-10-base, 1,10-phenanthroline-2-base, 1,10-phenanthroline-3-base, 1,10-phenanthroline-4-base, 1,10-phenanthroline-5-base, 2,9-phenanthroline-1-base, 2,9-phenanthroline-3-base, 2,9-phenanthroline-4-base, 2,9-phenanthroline-5-base, 2,9-phenanthroline-6-base, 2,9-phenanthroline-7-base, 2,9-phenanthroline-8-base, 2,9-phenanthroline-10-base, 2,8-phenanthroline-1-base, 2,8-phenanthroline-3-base, 2,8-phenanthroline-4-base, 2,8-phenanthroline-5-base, 2,8-phenanthroline-6-base, 2,8-phenanthroline-7-base, 2,8-phenanthroline-9-base, 2,8-phenanthroline-10-base, 2,7-phenanthroline-1-base, 2,7-phenanthroline-3-base, 2,7-phenanthroline-4-base, 2,7-phenanthroline-5-base, 2,7-phenanthroline-6-base, 2,7-phenanthroline-8-base, 2,7-phenanthroline-9-base and 2,7-phenanthroline-10-base; Phenazinyl comprises 1-phenazinyl and 2-phenazinyl; Phenothiazinyl comprises 1-phenothiazinyl, 2-phenothiazinyl, 3-phenothiazinyl, 4-phenothiazinyl and lysivane base; Phenoxazinyl comprises 1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl, 4-phenoxazinyl and 10-phenoxazinyl; Oxazolyl comprises 2-oxazolyl, 4-oxazolyl and 5-oxazolyl; Oxadiazole comprises 2-oxadiazole base and 5-oxadiazole base; The furazan base comprises 3-furazan base; Dibenzofuran group comprises 1-dibenzofuran group, 2-dibenzofuran group, 3-dibenzofuran group and 4-dibenzofuran group; The dibenzothiophene base comprises 1-dibenzothiophene base, 2-dibenzothiophene base, 3-dibenzothiophene base and 4-dibenzothiophene base.
Term used herein " (C1-C30) alkyl " comprises (C1-C20) alkyl or (C1-C10) alkyl, and term " (C6-C30) aryl " comprises (C6-C20) aryl.Term " (C2-C30) heteroaryl " comprises (C2-C20) heteroaryl, and term " (C3-C30) cycloalkyl " comprises (C3-C20) cycloalkyl or (C3-C7) cycloalkyl.Term " (C2-C30) alkenyl or alkynyl " comprises (C2-C20) alkenyl or alkynyl, perhaps (C2-C10) alkenyl or alkynyl.
In statement used herein " replacement or unsubstituted " (perhaps " having or do not have substituting group "), the unsubstituted substituting group of term " (the having substituting group) of replacement " expression further is substituted base and replaces.L 1, Ar 1, R 1To R 9, R and R 11To R 22Each substituting group one or more substituting groups that also can be selected from down group replace: deuterium, halogen, halogen replaces or unsubstituted (C1-C30) alkyl, (C6-C30) aryl, (C6-C30) aryl replaces or unsubstituted (C2-C30) heteroaryl, 5-to 7-unit Heterocyclylalkyl, with one or more aromatic ring condensed 5-to 7-unit Heterocyclylalkyl, (C3-C30) cycloalkyl, with one or more aromatic ring condensed (C6-C30) cycloalkyl, 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 lT-, R mC (=O)-, R mC (=O) O-, carboxyl, nitro and hydroxyl, wherein R aTo R lExpression (C1-C30) alkyl, (C6-C30) aryl or (C2-C30) heteroaryl independently; T is S or O; R mExpression (C1-C30) alkyl, (C1-C30) alkoxyl group, (C6-C30) aryl or (C6-C30) aryloxy.
Described organic electroluminescent compounds can be represented by following Chemical formula 2-9.
Chemical formula 2
Figure BDA00003206670000071
Chemical formula 3
Figure BDA00003206670000072
Chemical formula 4
Figure BDA00003206670000073
Chemical formula 5
Figure BDA00003206670000081
Chemical formula 6
Figure BDA00003206670000082
Chemical formula 7
Figure BDA00003206670000083
Chemical formula 8
Figure BDA00003206670000091
Chemical formula 9
Figure BDA00003206670000092
In the formula, X 2Be N or CH; Y is-O-,-S-,-C (R 11R 12)-or-N (R 15)-; L 1Expression singly-bound, replacement or unsubstituted (C6-C30) arylidene or replacement or unsubstituted (C2-C30) heteroarylidene; Ar 1Expression hydrogen, replacement or unsubstituted (C1-C30) alkyl, replacement or unsubstituted (C6-C30) aryl or replacement or unsubstituted (C2-C30) heteroaryl; R 1To R 9Represent hydrogen, deuterium, replacement or unsubstituted (C6-C30) aryl, replacement or unsubstituted (C2-C30) heteroaryl, NR independently 16R 17Or SiR 18R 19R 20R 11, R 12, R 15And R 16To R 20Represent hydrogen, deuterium, replacement or unsubstituted (C1-C30) alkyl, replacement or unsubstituted (C6-C30) aryl or replacement or unsubstituted (C2-C30) heteroaryl independently; Perhaps R 16And R 17Replacement that can be by having or do not have condensed ring or unsubstituted (C3-C30) alkenylene or replacement or unsubstituted (C3-C30) alkylidene group are connected and form alicyclic ring or monocycle or many cyclophanes ring, and the carbon atom of this alicyclic ring and monocycle or many cyclophanes ring can be replaced by one or more heteroatomss that are selected from N, O and S.
Particularly, X 2Expression N or CH; Y represents-O-,-S-,-C (R 11R 12)-or-N (R 15)-;
L 1Represent singly-bound or be selected from following structure arylidene:
Figure BDA00003206670000093
R 31And R 32Represent methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluor ethyl, trifluoroethyl, perfluoro propyl, perfluoro butyl, phenyl, naphthyl, pyridyl or quinolyl independently;
Ar 1Expression hydrogen, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluor ethyl, trifluoroethyl, perfluoro propyl, perfluoro butyl, phenyl, xenyl, terphenyl, naphthyl, 9,9-phenylbenzene fluorenyl, 9,9-dimethyl fluorenyl, fluoranthene base, pyridyl, dibenzofuran group, dibenzothiophene base or N-phenyl carbazole base, and Ar 1Phenyl, xenyl, terphenyl, naphthyl and carbazyl also can be replaced by one or more substituting groups that are selected from down group: deuterium, fluorine, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, the 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, the perfluor ethyl, trifluoroethyl, perfluoro propyl, perfluoro butyl, the triphenyl silyl, trimethyl silyl, the 3,5-dimethylphenyl silyl, the diphenyl methyl silyl, phenyl, naphthyl, 9,9-phenylbenzene fluorenyl, 9,9-dimethyl fluorenyl, phenylpyridyl, carbazyl, the fluoranthene base, dibenzofuran group and dibenzothiophene base; And
R 1To R 9Represent hydrogen, deuterium, phenyl, pyridyl, dibenzofuran group, dibenzothiophene base, amino or carbazyl independently; R 11, R 12And R 15Represent hydrogen, deuterium, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluor ethyl, trifluoroethyl, perfluoro propyl, perfluoro butyl, phenyl, xenyl, 9 independently, 9-phenylbenzene fluorenyl, 9,9-dimethyl fluorenyl, naphthyl, pyridyl, N-phenyl carbazole base or quinolyl, and R 11, R 12And R 15Phenyl also can be replaced by one or more substituting groups that are selected from down group: deuterium, halogen, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluor ethyl, trifluoroethyl, perfluoro propyl, perfluoro butyl, phenyl and naphthyl, and R 11And R 12Can be interconnected to form ring.
Organic electroluminescent compounds of the present invention can be enumerated as following compound, but they are not construed as limiting the present invention:
Figure BDA00003206670000111
Figure BDA00003206670000121
Figure BDA00003206670000131
Figure BDA00003206670000141
Figure BDA00003206670000161
Figure BDA00003206670000171
Figure BDA00003206670000181
Figure BDA00003206670000191
Figure BDA00003206670000201
Can shown in (for example) following scheme 1, prepare organic electroluminescent compounds of the present invention, but be not limited thereto.
[scheme 1]
Figure BDA00003206670000202
In scheme 1, ring A, X 1, X 2, L 1, Ar 1, R 1, R 2, R 3, a, b, c be defined identical with Chemical formula 1 with Z; Hal represents halogen.
A kind of organic electroluminescence device is provided, and it comprises first electrode; Second electrode; And one or more layers organic layer between described first electrode of insertion and second electrode, wherein said organic layer comprises one or more organic electroluminescent compounds of being represented by Chemical formula 1.Described organic layer comprises electroluminescence layer, and the organic electroluminescent compounds of Chemical formula 1 can be used as the matrix in the described electroluminescence layer.
In electroluminescence layer, when the organic electroluminescent compounds of Chemical formula 1 is used as matrix, comprise one or more phosphorescent dopants.Be used for the not concrete restriction of phosphorescent dopants of organic electroluminescence device of the present invention, but optional from the represented compound of following Chemical formula 10:
Chemical formula 10
M 1L 101L 102L 103
Wherein:
M 1Be the metal that is selected from the periodic table of elements the 7th family, the 8th family, the 9th family, the 10th family, the 11st family, the 13rd family, the 14th family, the 15th family and the 16th family, ligand L 101, L 102, and L 103Be independently selected from following structure:
R 201To R 203Represent that independently hydrogen, deuterium, halogen replacement or unsubstituted (C1-C30) alkyl, (C1-C30) alkyl replace or unsubstituted (C6-C30) aryl or halogen;
R 204To R 219Represent hydrogen independently, deuterium, replace or unsubstituted (C1-C30) alkyl, replace or unsubstituted (C1-C30) alkoxyl group, replace or unsubstituted (C3-C30) cycloalkyl, replace or unsubstituted (C2-C30) thiazolinyl, replace or unsubstituted (C6-C30) aryl, replace or unsubstituted list-(C1-C30) alkylamino or replacement or unsubstituted two-(C1-C30) alkylaminos, replace or unsubstituted list-(C6-C30) arylamino or replacement or unsubstituted two-(C6-C30) arylaminos, SF 5, replacement or unsubstituted three (C1-C30) alkyl silyl, replacement or unsubstituted two (C1-C30) alkyl (C6-C30) aryl silyl, replacement or unsubstituted three (C6-C30) aryl silyl, cyano group or halogen;
R 220To R 223Represent independently that hydrogen, deuterium, halogen replace or unsubstituted (C1-C30) alkyl or (C1-C30) alkyl replace or unsubstituted (C6-C30) aryl;
R 224And R 225Represent hydrogen, deuterium, replacement or unsubstituted (C1-C30) alkyl, replacement or unsubstituted (C6-C30) aryl or halogen, perhaps R independently 224And R 225(C3-C12) alkenylene that can be by having or do not have condensed ring or (C3-C12) alkylidene group be connected to form alicyclic ring and monocycle or many cyclophanes ring;
R 226Expression replaces or unsubstituted (C1-C30) alkyl, replacement or unsubstituted (C6-C30) aryl, replacement or unsubstituted (C2-C30) heteroaryl or halogen;
R 227To R 229Represent hydrogen, deuterium, replacement or unsubstituted (C1-C30) alkyl, replacement or unsubstituted (C6-C30) aryl or halogen independently; And
Figure BDA00003206670000221
R 231To R 242Represent that independently hydrogen, deuterium, halogen replace or unsubstituted (C1-C30) alkyl, (C1-C30) alkoxyl group, halogen, replacement or unsubstituted (C6-C30) aryl, cyano group, replacement or unsubstituted (C3-C30) cycloalkyl, perhaps they can be connected to form volution or condensed ring by alkylidene group or alkenylene and adjacent substituting group, perhaps can pass through alkylidene group or alkenylene and R 207Or R 208Be connected to form saturated or undersaturated condensed ring.
The dopant compound of Chemical formula 10 can be enumerated as following compound, but is not limited thereto:
Figure BDA00003206670000231
In organic electronic devices of the present invention, except the represented organic electroluminescent compounds of Chemical formula 1, 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 thereto.
In addition, in organic electroluminescence device of the present invention, except the represented organic electroluminescent compounds of Chemical formula 1, described organic layer can comprise that also one or more are selected from the metal or the complex 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 is represented, 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 the organic electroluminescence device of emission white 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 thereto.
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 placed 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 electric transmission compound and reductibility doping agent also preferably is set, perhaps the mixing zone of hole transport compound and oxidisability doping agent at least one surface of prepared electrode pair.In this case, because the electric transmission compound is reduced into negatively charged ion, thereby promotes electronics to inject and be transferred to electroluminescent medium from the mixing zone.In addition, because the oxidized formation positively charged ion of hole transport compound, thereby promote the hole to inject and be transferred to electroluminescent medium from the mixing zone.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 with two-layer or more multi-layered electroluminescence layer can prepare as charge generation layer by using the reductibility dopant layer.
Useful effect of the present invention
According to the present invention, organic electroluminescent compounds can have high-luminous-efficiency and can have excellent material lifetime, can be used for preparing the OLED device with extremely superior working life.
Embodiments of the present invention
Be example hereinafter, the electroluminescent character of organic electroluminescent compounds of the present invention, its preparation method and this device is described further with representative compounds of the present invention.But these embodiment only are used to the embodiment purpose is described, are not intended to limit the scope of the invention.
[preparation example 1] preparation compound 1
Figure BDA00003206670000241
The preparation of compound 1-1
With 2,4-two chloro-quinazolines (8.1 grams, 40.6 mmoles), phenyl-boron dihydroxide (5.0 grams, 40.6 mmoles), 200 milliliters, 50 milliliters ethanol of toluene and 50 ml waters mix, and add Pd (PPh again 3) 4(1.9 grams, 1.64 mmoles) and K 2CO 3(12.9 grams, 122 mmoles).This mixture was stirred 5 hours down at 120 ℃, and be cooled to room temperature, stop this reaction with 200 milliliters of aqueous ammonium chloride solutions then.With 500 milliliters of ethyl acetate (EA) this mixture is extracted, with 50 ml distilled waters it is washed again.Use anhydrous MgSO 4The organic layer that obtains is carried out drying, under reduced pressure, remove organic solvent.Subsequently, carry out filtered through silica gel and recrystallization, obtain compound 1-1 (6.6 grams, 68%).
The preparation of compound 1-2
Under refluxing to 7H-benzo [c] carbazole (8.9 grams, 41.10 mmoles), compound 1-1 (11.9 grams, 49.32 mmoles), Pd (OAc) 2(0.46 gram, NaOt-bu7.9 gram, 82.20 mmoles), 100 milliliters of toluene, P (t-bu) 3(2 milliliters, 4.11 mmoles, 50% toluene solution) stir.After 10 hours, this mixture is cooled to room temperature, and to wherein adding distilled water.With EA resulting mixture is extracted, use anhydrous MgSO 4Drying is carried out drying again under reduced pressure.Subsequently, carry out post and separate, obtain compound 1-2 (14.5 grams, 84%).
The preparation of compound 1-3
Compound 1-2 (14.3 grams, 33.98 mmoles) is inserted in single neck flask, form vacuum atmosphere, with argon gas this flask is filled again.Add THF (500 milliliters), under 0 ℃, this mixture was stirred 10 minutes.Add NBS (7.35 grams, 40.78 mmoles), at room temperature this mixture was stirred one day.Termination reaction extracts the gained mixture with distilled water and EA.Use anhydrous MgSO 4Organic layer is carried out drying, use Rotary Evaporators to remove and desolvate, re-use hexane and EA and carry out column chromatography, obtain compound 1-3 (14.6 grams, 85%) as photographic developer.
The preparation of compound 1-4
Compound 1-3 (13.2 grams, 26.30 mmoles) is inserted in single neck flask, form vacuum atmosphere, with argon gas this flask is filled again.Add 500 milliliters of THF, under-78 ℃, this mixture was stirred 10 minutes.Dropwise just adding-BuLi (hexane solution of 2.5M) (15.8 milliliters, 39.45 mmoles), under-78 ℃, this mixture was being stirred 1 hour 30 minutes.Add trimethyl borate (4.85 milliliters, 39.45 mmoles) down at-78 ℃.Stirred this mixture 30 minutes down at-78 ℃, at room temperature stirred then 4 hours.Termination reaction extracts the gained mixture with distilled water and EA.Use anhydrous MgSO 4Organic layer is carried out drying, use Rotary Evaporators to remove and desolvate, re-use hexane and EA and carry out column chromatography, obtain compound 1-4 (6.9 grams, 18.05 mmoles, 65%) as photographic developer.
The preparation of compound 1
Under refluxing with compound 1-4 (8.1 grams, 17.4 mmoles), 3-bromo-9-phenyl-9H-carbazole (6.7 grams, 20.88 mmoles), Pd (PPh 3) 4(0.8 gram, 0.7 mmole), 20 milliliters of 2M K 2CO 3The aqueous solution, 100 milliliters of toluene and 50 milliliters of ethanol stirred 12 hours.With distilled water this mixture is washed, and extract with EA.Use anhydrous MgSO 4Drying is under reduced pressure distilled, and carries out post and separate, and obtains compound 1 (6.8 grams, 10.3 mmoles, 58%).
MS/FAB:663 (actual measurement), 662.78 (calculating)
[preparation example 2] preparation compound 2
Figure BDA00003206670000261
The preparation of compound 2-1
With 2,4-two chloro-quinazolines (8.1 gram, 40.6 mmoles), xenyl phenyl-boron dihydroxide (8.0 grams, 40.6 mmoles), 200 milliliters of toluene, 50 milliliters of ethanol and 50 ml waters mix, and add Pd (PPh again 3) 4(1.9 grams, 1.64 mmoles) and K 2CO 3(12.9 grams, 122 mmoles).This mixture was stirred 5 hours down at 120 ℃, and be cooled to room temperature, with 200 milliliters of aqueous ammonium chloride solution termination reactions.With 500 milliliters of EA this mixture is extracted, it is washed with 50 ml distilled waters.Use anhydrous MgSO 4The organic layer that obtains is carried out drying, under reduced pressure, remove organic solvent.Subsequently, carry out filtered through silica gel and recrystallization, obtain compound 2-1 (8.2 grams, 25.9 mmoles, 64%).
The preparation of compound 2-2
Prepare compound 2-2 (9.5 grams, 19.1 mmoles, 74%) by the method identical with preparing compound 1-2.
The preparation of compound 2-3
Prepare compound 2-3 (9.0 grams, 15.6 mmoles, 82%) by the method identical with preparing compound 1-3.
The preparation of compound 2-4
Prepare compound 2-4 (4.0 grams, 7.4 mmoles, 47%) by the method identical with preparing compound 1-4.
The preparation of compound 2
Prepare compound 2 (2.8 restrain 4.6 mmoles, 51%) by the method identical by compound 2-4 (4.0 grams, 7.4 mmoles) and 3-bromo-9-phenyl-9H-carbazole (6.7 grams, 20.88 mmoles) with preparing compound 1.
MS/FAB:739 (actual measurement), 738.87 (calculating)
[preparation example 3] preparation compound 7
Figure BDA00003206670000271
The preparation of compound 7
Prepare compound 7 (2.8 restrain 4.6 mmoles, 51%) by the method identical by compound 2-4 (4.0 grams, 7.4 mmoles) and 2-bromo dibenzo [b, d] thiophene (5.5 grams, 20.88 mmoles) with preparing compound 1.
MS/FAB:604 (actual measurement), 603.73 (calculating)
[preparation example 4] preparation compound 12
Figure BDA00003206670000272
The preparation of compound 12
Prepare compound 12 (6.8 restrain 9.5 mmoles, 53%) by the method identical by compound 1-4 (6.9 grams, 18.05 mmoles) and 10-bromo-7-phenyl-7H-benzo [c] carbazole (7.8 grams, 20.88 mmoles) with preparing compound 1.
MS/FAB:713 (actual measurement), 712.84 (calculating).
[preparation example 5] preparation compound 16
Figure BDA00003206670000281
The preparation of compound 16
By compound 2-4 (9.8 grams, 18.05 mmoles) and 2-bromo-9,9-dimethyl-9H-fluorenes (5.7 grams, 20.88 mmoles) prepares compound 16 (7.6 restrain 11.0 mmoles, 61%) by the method identical with preparing compound 1.
MS/FAB:690 (actual measurement), 689.84 (calculating)
[preparation example 6] preparation compound 25
Figure BDA00003206670000282
The preparation of compound 6-1
7H-benzo [c] carbazole (20 grams, 92 mmoles) and 1-bromo-4-iodobenzene (43.5 grams, 184 mmoles) are dissolved in 500 milliliters of toluene, and add CuI (8.8 grams, 46 mmoles), diaminoethanes (6.2 milliliters, 92 mmoles) and K 3PO 4(8.7 grams, 276 mmoles) reflux this mixture 30 hours again.This mixture is cooled to room temperature, and stops this reaction with 50 milliliters of 2.0M HCl aqueous solution.With 1 liter of EA the gained mixture is extracted, with 50 ml distilled waters it is washed again.Use anhydrous MgSO 4The organic layer that obtains is carried out drying, under reduced pressure, remove organic solvent.Carry out silica gel column chromatography again, obtain compound 6-1 (19 grams, 56%).
The preparation of compound 6-2
Compound 6-1 (19 grams, 51 mmoles) is dissolved among 250 milliliters of THF, is cooled to-78 ℃ again, and is just adding-BuLi (hexane solution of 2.5M) (24.5 milliliters) down at-78 ℃.This mixture was stirred 1 hour down at-78 ℃, add B (OMe) 3(8.5 milliliters) stir this mixture 2 hours then, stop this reaction with 100 milliliters of aqueous ammonium chloride solutions.With 500 milliliters of EA the gained mixture is extracted, with 100 ml distilled waters it is washed again.Use anhydrous MgSO 4The organic layer that obtains is carried out drying, under reduced pressure, remove organic solvent.Carry out recrystallization then, obtain compound 6-2 (14 grams, 81%).
The preparation of compound 6-3
Compound 1-1 (3.3 gram, 13.7 mmoles) and compound 6-2 (5.5 grams, 16.4 mmoles) and 100 milliliters of toluene, 20 milliliters of ethanol and 20 ml waters are mixed adding Pd (PPh 3) 4(1.6 grams, 1.4 mmoles) and K 2CO 3(5.7 grams, 41.1 mmoles).This mixture was stirred 5 hours down at 120 ℃, and be cooled to room temperature, with 20 milliliters of aqueous ammonium chloride solution termination reactions.With 250 milliliters of EA this mixture is extracted, it is washed with 30 ml distilled waters.Use anhydrous MgSO 4The organic layer that obtains is carried out drying, under reduced pressure, remove organic solvent.Carry out filtered through silica gel and recrystallization then, obtain compound 6-3 (4.9 grams, 9.8 mmoles, 72%).
The preparation of compound 6-4
Prepare compound 6-4 (4.3 grams, 7.5 mmoles, 76%) by the method identical with preparing compound 1-3.
The preparation of compound 6-5
Prepare compound 6-5 (1.7 grams, 3.1 mmoles, 43%) by the method identical with preparing compound 1-4.
The preparation of compound 25
By the method identical with preparing compound 1 by compound 6-5 (9.8 grams, 18.05 mmoles) and 3-bromo-9-phenyl-9H-carbazole (6.7 grams, 20.88 mmoles) preparation compounds 25 (7.6 restrain 10.3 mmoles, 57%).
MS/FAB:739 (actual measurement), 738.87 (calculating)
[preparation example 7] preparation compound 37
Figure BDA00003206670000301
The preparation of compound 7-1
7H-benzo [c] carbazole (50 grams, 0.23 mole) is dissolved among 1.4 liters of DMF, adds NBS (41 grams, 0.23 mole), at ambient temperature this mixture was stirred 24 hours then.Behind the reaction terminating, the gained mixture is extracted, organic layer is distilled under reduced pressure with EA.Carry out silicagel column then and separate, obtain compound 7-1 (53.2 grams, 78%).
The preparation of compound 7-2
With compound 7-1 (30 grams, 0.10 mole), iodobenzene (22.6 milliliters, 0.20 mmole), CuI (9.6 grams, 0.05 mole), Cs 2CO 3(99 grams, 0.030 mole) and EDA (13.7 milliliters, 0.20 mole) are added in 500 milliliters of toluene, and stir 24 hours under refluxing.With EA this mixture is extracted, under reduced pressure, distill, and carry out post with MC/Hex and separate, obtain compound 7-2 (20 grams, 53%).
The preparation of compound 7-3
Compound 7-2 (18 gram, 48.4 mmoles) is dissolved among 250 milliliters of THF ,-78 ℃ add down 2.5M just-BuLi (in hexane) (23.2 milliliters, 58.0 mmoles), then this mixture was stirred 1 hour.Slowly add B (Oi-Pr) 3(16.7 milliliters, 72.5 mmoles) were with this solution stirring 2 hours.Add 2M HCl, and this mixture is carried out quencher and extraction with distilled water and EA.Re-use MC and Hex and carry out recrystallization, obtain compound 7-3 (13.6 grams, 83.4%).
The preparation of compound 7-4
With compound 7-3 (13.6 grams, 40.3 mmoles), bromo carbazole (9.9 grams, 40.3 mmoles), Pd (PPh 3) 4(2.3 grams, 2.0 mmoles), K 2CO 3(13.4 gram, 96.7 mmoles), 200 milliliters of toluene and 48 ml distilled waters mix, and stir 2 hours down at 90 ℃ again.Under reduced pressure, organic layer is distilled, and grind with MeOH.The solid that obtains is dissolved among the MC, and silicon-dioxide filters, and grinds with MC and hexane, obtains compound 7-4 (15 grams, 81%).
The preparation of compound 37
Compound 1-1 (4 grams, 16.6 mmoles) and compound 7-4 (7.6 grams, 16.6 mmoles) are suspended among 80 milliliters of DMF, add 60%NaH (1.1 grams, 28.2 mmoles) at ambient temperature, this mixture was stirred 12 hours.Add 1 liter of distilled water, and under reduced pressure, this mixture is filtered.With MeOH/EA the gained solid is ground, be dissolved among the MC, carry out silicon-dioxide and filter, grind with the MC/ normal hexane again, obtain compound 37 (2.4 grams, 21.8%).
The measured value 662.78 of MS/FAB, theoretical value 662.25
[preparation example 8] preparation compound 116
Figure BDA00003206670000311
The preparation of compound 8-1
With compound 7-1 (10 grams, 33.8 mmoles), dibenzo [b, d] furans-4-ylboronic acid (8.6 grams, 40.56 mmoles), Pd (PPh 3) 4(2 grams, 1.7 mmoles), K 2CO 3(34 grams, 321 mmoles), 60 milliliters of toluene, 12 milliliters of EtOH and 12 milliliters of purified water are mixed, and stir 15 hours down at 120 ℃ again.Behind the reaction terminating, the gained mixture is left standstill, remove water layer, then organic layer is concentrated.Carry out the silicagel column purifying then, obtain compound 8-1 (10.2 grams, 78%).
The preparation of compound 116
Compound 8-1 (3 grams, 7.8 mmoles) and compound 2-1 (2.1 grams, 7.8 mmoles) are suspended among 30 milliliters of DMF, add 60%NaH (376 milligrams, 9.4 mmoles) at ambient temperature, this mixture was stirred 12 hours.Add 500 milliliters of purified water, and under reduced pressure, this mixture is filtered.With MeOH/EA, DMF and EA/THF the solid that obtains is ground successively.The product that obtains is dissolved among the MC, and silicon-dioxide filters, and grinds with MeOH/EA, obtains compound 116 (2.4 grams, 46%).
The measured value 663.76 of MS/FAB, theoretical value 663.23
[preparation example 9] preparation compound 128
Figure BDA00003206670000321
The preparation of compound 9-1
With 3-bromo-9H-carbazole (5 grams, 20.32 mmoles), dibenzo [b, d] furans-4-ylboronic acid (4.7 grams, 22.35 mmoles), K 2CO 3(7 grams, 50.79 mmoles), Pd (PPh 3) 4(1.17 grams, 1.01 mmoles), 100 milliliters of toluene, 25 milliliters of EtOH and 25 milliliters of purified water are mixed, and stir 3 hours down at 100 ℃ again.Behind the reaction terminating, this mixture is cooled to room temperature, it is left standstill, remove water layer.Organic layer is concentrated, re-use silicagel column and carry out purifying, obtain compound 9-1 (4.3 grams, 64%).
The preparation of compound 128
Compound 2-1 (3 grams, 8.99 mmoles) and compound 9-1 (3.14 grams, 9.89 mmoles) are suspended in 50 milliliters of dry DMF, at room temperature add 60%NaH (0.54 gram, 13.5 mmoles).Stirred this mixture 5 hours under the room temperature.Behind the reaction terminating, dropwise add 3 milliliters of MeOH,, carry out the silicagel column purifying, suspend, filter, carry out crystallization with THF again, obtain compound 128 (1 gram, 18%) with EA owing to excessive MeOH obtains solid.
The measured value 613.70 of MS/FAB, theoretical value 613.22
[embodiment 1] uses organic electroluminescent compounds of the present invention to prepare the OLED device
Use the compound of organic electronic 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, are stored in the Virahol before using.Then, the ITO substrate is contained in the substrate folder (folder) of vacuum sediment equipment, N 1, N 1 '-([1,1 '-xenyl]-4,4 '-two bases) two (N 1-(naphthalene-1-yl)-N 4, N 4-diphenyl benzene-1,4-diamines place the cell (cell) of vacuum sediment equipment, are vented to indoor vacuum tightness then and are up to 10 -6Holder.Then, apply electric current to described cell and make its evaporation, thereby deposit thickness is the hole injection layer of 60 nanometers on the ITO substrate.Subsequently, with N, N '-two (4-xenyl)-N, N '-two (4-xenyl)-4,4 '-benzidine base places another cell of vacuum sediment equipment, by applying electric current to this cell so that NPB evaporation, thereby deposit thickness is the hole transmission layer of 20 nanometers on described hole injection layer.After forming hole injection layer and hole transmission layer, form electroluminescence layer in the above, specific as follows.In vacuum vapor deposition equipment, will place a cell as the compound 1 of matrix, will place another cell as the Compound D-11 of doping agent.Make this two kinds of materials evaporation with different speed, make the doping that 4 weight % take place, thereby thickness is that the electroluminescence layer vapour deposition of 30 nanometers is on hole transmission layer.Subsequently, (4-(9 with 2-, 10-two (naphthalene-2-yl) anthracene-2-yl) phenyl)-1-phenyl-1H-benzo [d] imidazoles places a cell, quinoline is closed in another cell of lithium, then these two kinds of materials are evaporated with identical speed, make that 50 weight % take place to mix, thereby vapour deposition thickness is the electron transfer layer of 30 nanometers on described electroluminescence layer.Then, vapour deposition thickness be the Liq (quinoline closes lithium) of 2 nanometers as electron injecting layer, using another vacuum vapor deposition equipment to come vapour deposition thickness then is the Al negative electrode of 150 nanometers, thereby makes OLED.
Before use, each compound that is used for the OLED device passes through 10 -6Holder vacuum-sublimation down is able to purifying.
The result is that it is 8.8 milliamperes/centimetre that confirmation electric current under the voltage of 4.4V flows 2, and emission 900cd/m 2Ruddiness.
[embodiment 2] use organic electroluminescent compounds of the present invention to prepare the OLED device
Use the method identical with embodiment 1 to make the OLED device, difference is, uses compound 2 as substrate material in electroluminescence layer, and use D-7 is as doping agent.
The result is that it is 22.9 milliamperes/centimetre that confirmation electric current under the voltage of 4.9V flows 2, and emission 2710cd/m 2Ruddiness.
[embodiment 3] use organic electroluminescent compounds of the present invention to prepare the OLED device
Use the method identical with embodiment 1 to make the OLED device, difference is that use compound 25 is as substrate material in electroluminescence layer.
The result is that it is 16.9 milliamperes/centimetre that confirmation electric current under the voltage of 4.8V flows 2, and emission 1780cd/m 2Ruddiness.
[embodiment 4] use organic electroluminescent compounds of the present invention to prepare the OLED device
Use the method identical with embodiment 1 to make the OLED device, difference is, uses compound 37 as substrate material in electroluminescence layer, and use D-7 is as doping agent.
The result is that it is 41.2 milliamperes/centimetre that confirmation electric current under the voltage of 5.5V flows 2, and emission 4800cd/m 2Ruddiness.
[embodiment 5] use organic electroluminescent compounds of the present invention to prepare the OLED device
Use the method identical with embodiment 1 to make the OLED device, difference is, uses compound 128 as substrate material in electroluminescence layer, and use D-7 is as doping agent.
The result is to confirm the mobile 8.7mA/cm of being of electric current under the voltage of 4.2V 2, and emission 900cd/m 2Ruddiness.
[embodiment 6] use organic electroluminescent compounds of the present invention to prepare the OLED device
Use the method identical with embodiment 1 to make the OLED device, difference is, uses compound 139 as substrate material in electroluminescence layer, and use D-7 is as doping agent.
The result is to confirm the mobile 3.2mA/cm of being of electric current under the voltage of 4.1V 2, and emission 400cd/m 2Ruddiness.
The electroluminescent character of the OLED device of the electroluminescent material of [comparative example 1] use prior art
Make the OLED device by the method identical with embodiment 1, difference is, use 4,4 '-N, N '-two carbazoles-xenyl obtains electroluminescence layer as doping agent by vapour deposition as matrix and Compound D-11, and using the vapour deposition between described electroluminescence layer and electron transfer layer of two (2-methyl-oxine closes (quinolinato)) 4-phenylphenol aluminium (III) to obtain thickness is the hole blocking layer of 10 nanometers.
The result is to confirm the mobile 20.0mA/cm of being of electric current under the voltage of 8.2V 2, and emission 1000cd/m 2Ruddiness.
Confirmation is than conventional material, and organic electroluminescent compounds of the present invention shows excellent electroluminescent character.Use organic electroluminescent compounds of the present invention can show excellent electroluminescent character and can reduce operating voltage, thereby increase power efficiency as the device of substrate material, and and then improvement watt consumption.
Though described preferred implementation of the present invention for illustration purposes, it will be understood by those skilled in the art that various improvement, increase and alternative also are possible, the scope and spirit of the present invention that do not deviate from appended claims and limited.
Industrial applicability
According to the present invention, organic electroluminescent compounds can have high-luminous-efficiency and can have excellent material lifetime, can be used for preparing the OLED device with extremely superior working life.

Claims (10)

1. organic electroluminescent compounds of representing by following Chemical formula 1:
Chemical formula 1
Figure FDA00003206669900011
Wherein:
Ring A represents monocycle or many cyclophanes ring;
X 1And X 2Represent N or CR ' independently;
L 1Expression singly-bound, replacement or unsubstituted (C6-C30) arylidene, replacement or unsubstituted (C2-C30) heteroarylidene or replacement or unsubstituted (C3-C30) ring alkylidene group;
Ar 1Expression hydrogen, deuterium, halogen, replacement or unsubstituted (C1-C30) alkyl, replacement or unsubstituted (C6-C30) aryl or replacement or unsubstituted (C2-C30) heteroaryl;
Z is independently selected from following structure:
Figure FDA00003206669900012
And when described ring A was monocyclic aromatic rings, Z only was selected from following structure:
Figure FDA00003206669900013
Y represents-O-,-S-,-C (R 11R 12)-,-Si (R 13R 14)-or-N (R 15)-;
R 1To R 9Represent hydrogen independently, deuterium, halogen, replace or unsubstituted (C1-C30) alkyl, replace or unsubstituted (C6-C30) aryl, replace or unsubstituted (C2-C30) heteroaryl, replace or unsubstituted (C3-C30) cycloalkyl, replace or unsubstituted 5-to 7-unit Heterocyclylalkyl, replace or unsubstituted (C6-C30) aryl (C1-C30) alkyl, replacement or unsubstituted (C6-C30) aryl Cycloalkylfused with one or more (C3-C30), with replacement or the first Heterocyclylalkyl of unsubstituted one or more aromatic ring condensed 5-to 7-, with replacement or unsubstituted one or more aromatic ring condensed (C3-C30) cycloalkyl,-NR 16R 17,-SiR 18R 19R 20,-SR 21,-OR 22, cyano group, nitro or hydroxyl; Perhaps R 1To R 9Replacement that can be by having or do not have condensed ring or unsubstituted (C3-C30) alkenylene or replacement or unsubstituted (C3-C30) alkylidene group link to each other with adjacent substituting group and form alicyclic ring and monocycle or many cyclophanes ring, and the carbon atom of described alicyclic ring and monocycle or many cyclophanes ring can be replaced by one or more heteroatomss that are selected from N, O and S;
R ' and R 11To R 22Represent hydrogen, deuterium, halogen, replacement or unsubstituted (C1-C30) alkyl, replacement or unsubstituted (C6-C30) aryl, replacement or unsubstituted (C2-C30) heteroaryl, replacement or unsubstituted 5-to 7-unit's Heterocyclylalkyl or replacement or unsubstituted (C3-C30) cycloalkyl independently; Perhaps replacement that they can be by having or do not have condensed ring or unsubstituted (C3-C30) alkenylene or replacement or unsubstituted (C3-C30) alkylidene group link to each other with adjacent substituting group and form alicyclic ring and monocycle or many cyclophanes ring, and the carbon atom of described alicyclic ring and monocycle or many cyclophanes ring can be replaced by one or more heteroatomss that are selected from N, O and S;
A, c, e and i represent 1 to 4 integer independently, and when a, c, e and I be during more than or equal to 2 integer, each R 1, R 3, R 5And R 9Can be identical or differ from one another;
B, d and g represent 1 to 3 integer independently, and when b, d and g be during more than or equal to 2 integer, each R 2, R 4And R 7Can be identical or differ from one another;
F represents 1 to 6 integer, and when f be during more than or equal to 2 integer, each R 6Can be identical or differ from one another;
H represents 1 to 5 integer, and when h be during more than or equal to 2 integer, each R 8Can be identical or differ from one another; And
Described hetero-aromatic ring, heteroarylidene, Heterocyclylalkyl and 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, each substituting group L 1, Ar 1, R 1To R 9, R and R 11To R 22The one or more substituting groups that also are selected from down group replace: deuterium, halogen, halogen replaces or unsubstituted (C1-C30) alkyl, (C6-C30) aryl, (C6-C30) aryl replaces or unsubstituted (C2-C30) heteroaryl, 5-to 7-unit Heterocyclylalkyl, with one or more aromatic ring condensed 5-to 7-unit Heterocyclylalkyl, (C3-C30) cycloalkyl, with one or more aromatic ring condensed (C6-C30) cycloalkyl, 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 lT-, R mC (=O)-, R mC (=O) O-, carboxyl, nitro and hydroxyl, wherein R aTo R lExpression (C1-C30) alkyl, (C6-C30) aryl or (C2-C30) heteroaryl independently; T is S or O; 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 is characterized in that, described compound is selected from by the represented compound of following Chemical formula 2-9:
Chemical formula 2
Chemical formula 3
Figure FDA00003206669900032
Chemical formula 4
Figure FDA00003206669900033
Chemical formula 5
Figure FDA00003206669900041
Chemical formula 6
Figure FDA00003206669900042
Chemical formula 7
Figure FDA00003206669900043
Chemical formula 8
Figure FDA00003206669900051
Chemical formula 9
Figure FDA00003206669900052
In the formula, X 2Be N or CH; Y is-O-,-S-,-C (R 11R 12)-or-N (R 15)-; L 1Expression singly-bound, replacement or unsubstituted (C6-C30) arylidene or replacement or unsubstituted (C2-C30) heteroarylidene; Ar 1Expression hydrogen, replacement or unsubstituted (C1-C30) alkyl, replacement or unsubstituted (C6-C30) aryl or replacement or unsubstituted (C2-C30) heteroaryl; R 1To R 9Represent hydrogen, deuterium, replacement or unsubstituted (C6-C30) aryl, replacement or unsubstituted (C2-C30) heteroaryl, NR independently 16R 17Or SiR 18R 19R 20R 11, R 12, R 15And R 16To R 20Represent hydrogen, deuterium, replacement or unsubstituted (C1-C30) alkyl, replacement or unsubstituted (C6-C30) aryl or replacement or unsubstituted (C2-C30) heteroaryl independently; Perhaps R 16And R 17Replacement that can be by having or do not have condensed ring or unsubstituted (C3-C30) alkenylene or replacement or unsubstituted (C3-C30) alkylidene group are connected and form alicyclic ring or monocycle or many cyclophanes ring, and the carbon atom of described alicyclic ring and monocycle or many cyclophanes ring can be replaced by one or more heteroatomss that are selected from N, O and S.
4. organic electroluminescent compounds as claimed in claim 3 is characterized in that X 2Expression N or CH; Y represents-O-,-S-,-C (R 11R 12)-or-N (R 15)-;
L 1Represent singly-bound or be selected from following structure arylidene:
Figure FDA00003206669900053
R 31And R 32Represent methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluor ethyl, trifluoroethyl, perfluoro propyl, perfluoro butyl, phenyl, naphthyl, pyridyl or quinolyl independently;
Ar 1Expression hydrogen, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluor ethyl, trifluoroethyl, perfluoro propyl, perfluoro butyl, phenyl, xenyl, terphenyl, naphthyl, 9,9-phenylbenzene fluorenyl, 9,9-dimethyl fluorenyl, fluoranthene base, pyridyl, dibenzofuran group, dibenzothiophene base or N-phenyl carbazole base, and Ar 1Phenyl, xenyl, terphenyl, naphthyl and carbazyl also can be replaced by one or more substituting groups that are selected from down group: deuterium, fluorine, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, the 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, the perfluor ethyl, trifluoroethyl, perfluoro propyl, perfluoro butyl, the triphenyl silyl, trimethyl silyl, the 3,5-dimethylphenyl silyl, the diphenyl methyl silyl, phenyl, naphthyl, 9,9-phenylbenzene fluorenyl, 9,9-dimethyl fluorenyl, phenylpyridyl, carbazyl, the fluoranthene base, dibenzofuran group and dibenzothiophene base; And
R 1To R 9Represent hydrogen, deuterium, phenyl, pyridyl, dibenzofuran group, dibenzothiophene base, amino or carbazyl independently; R 11, R 12And R 15Represent hydrogen, deuterium, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluor ethyl, trifluoroethyl, perfluoro propyl, perfluoro butyl, phenyl, xenyl, 9 independently, 9-phenylbenzene fluorenyl, 9,9-dimethyl fluorenyl, naphthyl, pyridyl, N-phenyl carbazole base or quinolyl, and R 11, R 12And R 15Phenyl also can be replaced by one or more substituting groups that are selected from down group: deuterium, halogen, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluor ethyl, trifluoroethyl, perfluoro propyl, perfluoro butyl, phenyl and naphthyl, and R 11And R 12Can be interconnected to form ring.
5. organic electroluminescent compounds as claimed in claim 4 is characterized in that, this compound is selected from following compound:
Figure FDA00003206669900071
Figure FDA00003206669900081
Figure FDA00003206669900091
Figure FDA00003206669900101
Figure FDA00003206669900111
Figure FDA00003206669900121
Figure FDA00003206669900131
Figure FDA00003206669900151
Figure FDA00003206669900161
6. organic electroluminescence device, this device comprises as each described organic electroluminescent compounds among the claim 1-5.
7. organic electroluminescence device as claimed in claim 6 is characterized in that described device comprises first electrode; Second electrode; Insert one or more layers organic layer between described first electrode and second electrode, wherein said organic layer comprises one or more organic electroluminescent compounds and one or more phosphorescent dopants by following Chemical formula 10 expression,
Chemical formula 10
M 1L 101L 102L 103
Wherein:
M 1Be the metal that is selected from the periodic table of elements the 7th family, the 8th family, the 9th family, the 10th family, the 11st family, the 13rd family, the 14th family, the 15th family and the 16th family, ligand L 101, L 102, and L 103Be independently selected from following structure:
Figure FDA00003206669900162
R 201To R 203Represent that independently hydrogen, deuterium, halogen replacement or unsubstituted (C1-C30) alkyl, (C1-C30) alkyl replace or unsubstituted (C6-C30) aryl or halogen;
R 204To R 219Represent hydrogen independently, deuterium, replace or unsubstituted (C1-C30) alkyl, replace or unsubstituted (C1-C30) alkoxyl group, replace or unsubstituted (C3-C30) cycloalkyl, replace or unsubstituted (C2-C30) thiazolinyl, replace or unsubstituted (C6-C30) aryl, replace or unsubstituted list-(C1-C30) alkylamino or replacement or unsubstituted two-(C1-C30) alkylaminos, replace or unsubstituted list-(C6-C30) arylamino or replacement or unsubstituted two-(C6-C30) arylaminos, SF 5, replacement or unsubstituted three (C1-C30) alkyl silyl, replacement or unsubstituted two (C1-C30) alkyl (C6-C30) aryl silyl, replacement or unsubstituted three (C6-C30) aryl silyl, cyano group or halogen;
R 220To R 223Represent independently that hydrogen, deuterium, halogen replace or unsubstituted (C1-C30) alkyl or (C1-C30) alkyl replace or unsubstituted (C6-C30) aryl;
R 224And R 225Represent hydrogen, deuterium, replacement or unsubstituted (C1-C30) alkyl, replacement or unsubstituted (C6-C30) aryl or halogen, perhaps R independently 224And R 225(C3-C12) alkenylene that can be by having or do not have condensed ring or (C3-C12) alkylidene group be connected to form alicyclic ring and monocycle or many cyclophanes ring;
R 226Expression replaces or unsubstituted (C1-C30) alkyl, replacement or unsubstituted (C6-C30) aryl, replacement or unsubstituted (C2-C30) heteroaryl or halogen;
R 227To R 229Represent hydrogen, deuterium, replacement or unsubstituted (C1-C30) alkyl, replacement or unsubstituted (C6-C30) aryl or halogen independently; And
Q represents
Figure FDA00003206669900181
Or
Figure FDA00003206669900182
R 231To R 242Represent that independently hydrogen, deuterium, halogen replace or unsubstituted (C1-C30) alkyl, (C1-C30) alkoxyl group, halogen, replacement or unsubstituted (C6-C30) aryl, cyano group or replacement or unsubstituted (C3-C30) cycloalkyl, perhaps they can be connected to form volution or condensed ring by alkylidene group or alkenylene and adjacent substituting group, perhaps can pass through alkylidene group or alkenylene and R 207Or R 208Be connected to form saturated or unsaturated condensed ring.
8. organic electroluminescence device as claimed in claim 7 is characterized in that, described phosphorescent dopants is selected from following compound:
Figure FDA00003206669900183
9. organic electroluminescence device as claimed in claim 7 is characterized in that described organic layer comprises electroluminescence layer and charge generation layer.
10. organic electroluminescence device as claimed in claim 7 is characterized in that described organic layer also comprises the organic electro luminescent layer of one or more layers red-emitting, green glow and blue light, with the emission white light.
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