WO2011132865A1 - 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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WO2011132865A1
WO2011132865A1 PCT/KR2011/002293 KR2011002293W WO2011132865A1 WO 2011132865 A1 WO2011132865 A1 WO 2011132865A1 KR 2011002293 W KR2011002293 W KR 2011002293W WO 2011132865 A1 WO2011132865 A1 WO 2011132865A1
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organic electroluminescent
alkyl
aryl
heteroaryl
arylsilyl
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PCT/KR2011/002293
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French (fr)
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Hee Choon Ahn
Young Jun Cho
Hyuck Joo Kwon
Bong Ok Kim
Sung Min Kim
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Rohm And Haas Electronic Materials Korea Ltd.
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    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device using the same, more particularly, to novel organic electroluminescent compounds used as an electroluminescent material and an organic electroluminescent device using the same.
  • electroluminescent material The most important factor to determine luminous efficiency in an organic light-emitting diode (OLED) is electroluminescent material.
  • fluorescent materials have been widely used as electroluminescent material up to the present, development of phosphorescent materials is one of the best ways to improve the luminous efficiency theoretically up to four (4) times, in view of electroluminescent mechanism.
  • iridium (III) complexes have been widely known as phosphorescent material, including (acac)Ir(btp) 2 , Ir(ppy) 3 and Firpic, as the red, green and blue one, respectively.
  • a lot of phosphorescent materials have been recently investigated in Japan, Europe and America.
  • CBP is most widely known as a host material for a phosphorescent material.
  • High-efficiency OLEDs using a hole blocking layer comprising BCP, BAlq, etc. are reported.
  • High-performance OLEDs using BAlq derivatives as a host were reported by Pioneer (Japan) and others.
  • the object of the present invention is to provide organic electroluminescent compounds having the backbone to provide better luminous efficiency and device life with appropriate color coordinate as compared to conventional dopant material, while overcoming the problems described above, and an organic electroluminescent device having high luminous efficiency and improved life property.
  • organic electroluminescent compound represented by following Chemical Formula 1 and an organic electroluminescent device using the same. Since the organic electroluminescent compound according to the present invention exhibits good luminous efficiency and excellent life property compared to the existing host material, it may be used to manufacture OLED devices having very superior operation life.
  • X represents N(Ar 3 ), S or O;
  • Ar 1 through Ar 3 independently represent (C1-C30)alkyl, (C3-C30)cycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, 5- to 7-membered heterocycloalkyl containing one or more nitrogen atom(s), (C6-C30)aryl, (C3-C30)heteroaryl, or ;
  • alkyl, cycloalkyl, alkenyl, alkynyl, heterocycloalkyl, aryl or heteroaryl of Ar 1 through Ar 3 may be further substituted by R 11 ;
  • R 11 represents (C6-C30)aryl, (C3-C30)heteroaryl, or ;
  • R 1 and R 2 independently represent hydrogen, deuterium, (C1-C30)alkyl, halogen, cyano, morpholino, thiomorpholino, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C7-C30)bicycloalkyl, adamantyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C1-C30)alkoxy, (C6-C30)aryloxy, (C3-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)arylthio, mono- or di(C1-C30)alkylamino, mono- or di(C6-C30)arylamino, tri(C1-C30)alkylsily
  • R 12 through R 14 and R 15 through R 19 are the same as R 1 and R 2 ;
  • n and n independently represent an integer from 1 to 4.
  • R 1 and R 2 may be identical or different.
  • alkyl alkoxy and other substituents containing “alkyl” moiety include both linear and branched species.
  • aryl means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring, including a plurality of aryl groups having single bond(s) therebetween.
  • Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto.
  • the naphthyl includes 1-naphthyl and 2-naphthyl.
  • the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
  • the heteroaryl also includes heteroaryl groups having single bond(s) therebetween.
  • the heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt.
  • Specific examples include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzoisothi
  • the alkyl moiety of "(C1-C30)alkyl, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyloxy, (C1-C30)alkylthio" or the like may have 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms.
  • the aryl moiety of "(C6-C30)aryl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)aryloxy, (C6-C30)arylthio” or the like may have 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms.
  • the heteroaryl of "(C3-C30)heteroaryl” may have 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms.
  • the cycloalkyl of "(C3-C30)cycloalkyl” may have 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms.
  • the alkenyl or alkynyl of "(C2-C30)alkenyl or alkynyl” may have 2 to 20 carbon atoms, more specifically 2 to 10 carbon atoms.
  • the R 1 and R 2 independently represent hydrogen, deuterium, (C1-C30)alkyl, halogen, cyano, morpholino, thiomorpholino, (C6-C30)aryl, (C3-C30)heteroaryl, (C6-C30)arylthio, mono- or di(C1-C30)alkylamino, mono- or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, nitro or hydroxyl, and the alkyl, aryl, heteroaryl, arylthio, alkylamino, arylamino, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R 1 and R 2 may be further substituted by one or more substituent(s) selected from the group consisting of (
  • the Ar 1 through Ar 3 are independently selected from the following structures but are not limited thereto:
  • R 21 represents hydrogen or R 11 ;
  • R 22 represents R 11 ;
  • R 11 is the same as defined in Chemical Formula 1;
  • w represents an integer 1 or 2;
  • x represents an integer from 1 to 5;
  • y represents an integer from 1 to 3; and
  • z represents an integer from 1 to 4.
  • Ar 1 through Ar 3 independently represent a substituent selected from following structures but are limited thereto:
  • organic electroluminescent compound according to the present invention may be specifically exemplified as following compounds but the present invention is not limited thereto:
  • an organic electroluminescent device which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compound(s) of Chemical Formula 1.
  • the organic layer comprises an electroluminescent layer including one or more phosphorescent dopant when one or more organic electroluminescent compounds of Chemical Formula 1 are used as the electroluminescent host.
  • the dopant used in the organic electroluminescent device of the present invention is not particularly limited.
  • the organic electroluminescent device may comprise one or more organic electroluminescent compounds of Chemical Formula 1 and further comprises one or more amine compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds.
  • the organic layer may further comprise one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s) as well as one or more organic electroluminescent compounds of Chemical Formula 1.
  • the organic layer may comprise an electroluminescent layer and a charge generating layer.
  • the organic electroluminescent device is a white light-emitting organic electroluminescent device wherein the organic layer further comprises one or more organic electroluminescent layer(s) emitting blue, red or green light.
  • the organic electroluminescent compound according to the present invention is used as a host material of an organic electroluminescent material in an OLED device, it exhibits good luminous efficiency and excellent life property. Accordingly, it may be used to manufacture OLED devices having very superior operation life.
  • Organic electroluminescent compounds were prepared according to the procedure of Preparation Examples 1 and 2. 1 H NMR and MS/FAB data of thus prepared organic electroluminescent compounds are given in Table 1.
  • An OLED device was manufactured using the electroluminescent material according to the present invention.
  • a transparent electrode ITO thin film (15 ⁇ / ⁇ ) obtained from a glass for OLED (produced by Samsung Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
  • an ITO substrate was equipped in a substrate folder of a vacuum vapor deposition apparatus, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum vapor deposition apparatus, which was then ventilated up to 10 -6 torr of vacuum in the chamber. Then, electric current was applied to the cell to evaporate 2-TNATA, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • 2-TNATA 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine
  • N , N '-bis( ⁇ -naphthyl)- N , N '-diphenyl-4,4'-diamine (NPB) was placed in another cell of the vacuum vapor deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • the compounds purified by vacuum sublimation at 10 -6 torr (e.g., Compound 2, 9, 18, 25, 37, 41, 50, 70 or 95) were placed in a cell of a vacuum vapor deposition apparatus as a host, and an electroluminescent dopant (e.g., (piq) 2 Ir(acac) [bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate]) was placed in another cell as a dopant.
  • the two materials were evaporated at different rates such that an electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer through doping at 4 to 20 wt%.
  • An OLED was manufactured in the same manner as that of Example 1 except that 4,4'-bis(carbazol-9-yl)biphenyl (CBP) instead of the electroluminescent compounds of the present invention was used as a host material at another cell of the vacuum vapor deposition apparatus after forming the hole injection layer and the hole transport layer.
  • CBP 4,4'-bis(carbazol-9-yl)biphenyl
  • An OLED was manufactured in the same manner as that of Example 1 except that 4,4'-bis(carbazol-9-yl)biphenyl (CBP) instead of the compounds of the present invention as a host material at one cell of the vacuum vapor deposition apparatus and Bis(2-methyl-8-quinolinato)(p-phenyl-phenolato)aluminum(III) (BAlq) as a hole blocking layer were used.
  • CBP 4,4'-bis(carbazol-9-yl)biphenyl
  • BAlq Bis(2-methyl-8-quinolinato)(p-phenyl-phenolato)aluminum(III)
  • the organic electroluminescent compounds according to the present invention as a red light emitting material have luminous properties similar to or superior to the conventional material.
  • the device using the organic electroluminescent compound according to the present invention as a host material without using a hole blocking layer has excellent luminescent efficiency, drops driving voltage, and increases power efficiency, thereby reducing power consumption.
  • the organic electroluminescent compound according to the present invention is used as a host material of an organic electroluminescent material in an OLED device, it exhibits good luminous efficiency and excellent life property. Accordingly, it may be used to manufacture OLED devices having very superior operation life.

Abstract

Disclosed are organic electroluminescent compounds and organic electroluminescent devices employing said compounds. The organic electroluminescent compounds of the invention are substituted dihydro-pyrrolo[3,2-b:4,5-b']diindole, dihydro-furo[3,2-b:4,5-b']diindole and dihydro-thieno[3,2-b:4,5-b']diindole compounds defined by chemical formula (1), The compounds, when used in as a host material of an OLED device, exhibit good luminous efficiency and lifespan.

Description

NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
The present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device using the same, more particularly, to novel organic electroluminescent compounds used as an electroluminescent material and an organic electroluminescent device using the same.
The most important factor to determine luminous efficiency in an organic light-emitting diode (OLED) is electroluminescent material. Though fluorescent materials have been widely used as electroluminescent material up to the present, development of phosphorescent materials is one of the best ways to improve the luminous efficiency theoretically up to four (4) times, in view of electroluminescent mechanism. Up to now, iridium (III) complexes have been widely known as phosphorescent material, including (acac)Ir(btp)2, Ir(ppy)3 and Firpic, as the red, green and blue one, respectively. In particular, a lot of phosphorescent materials have been recently investigated in Japan, Europe and America.
Figure PCTKR2011002293-appb-I000001
At present, CBP is most widely known as a host material for a phosphorescent material. High-efficiency OLEDs using a hole blocking layer comprising BCP, BAlq, etc. are reported. High-performance OLEDs using BAlq derivatives as a host were reported by Pioneer (Japan) and others.
Figure PCTKR2011002293-appb-I000002
Although these materials provide good electroluminescence characteristics, they are disadvantageous in that degradation may occur during the high-temperature deposition process in vacuum because of low glass transition temperature and poor thermal stability. Since the power efficiency of an OLED is given by (π / voltage) × current efficiency, the power efficiency is inversely proportional to the voltage. High power efficiency is required to reduce the power consumption of an OLED. Actually, OLEDs using phosphorescent materials provide much better current efficiency (cd/A) than those using fluorescent materials. However, when the existing materials such as BAlq, CBP, etc. are used as a host of the phosphorescent material, there is no significant advantage in power efficiency (lm/W) over the OLEDs using fluorescent materials because of high driving voltage. Further, the OLED devices do not have satisfactory operation life. Therefore, development of more stable, higher-performance host materials is required.
With intensive efforts to overcome the problems of conventional techniques as described above, the present inventors have invented novel electroluminescent compounds which realize organic electroluminescent devices having excellent luminous efficiency and noticeably improved life property.
The object of the present invention is to provide organic electroluminescent compounds having the backbone to provide better luminous efficiency and device life with appropriate color coordinate as compared to conventional dopant material, while overcoming the problems described above, and an organic electroluminescent device having high luminous efficiency and improved life property.
Provided are a novel organic electroluminescent compound represented by following Chemical Formula 1 and an organic electroluminescent device using the same. Since the organic electroluminescent compound according to the present invention exhibits good luminous efficiency and excellent life property compared to the existing host material, it may be used to manufacture OLED devices having very superior operation life.
[Chemical Formula 1]
Figure PCTKR2011002293-appb-I000003
wherein
X represents N(Ar3), S or O;
Ar1 through Ar3 independently represent (C1-C30)alkyl, (C3-C30)cycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, 5- to 7-membered heterocycloalkyl containing one or more nitrogen atom(s), (C6-C30)aryl, (C3-C30)heteroaryl,
Figure PCTKR2011002293-appb-I000004
or
Figure PCTKR2011002293-appb-I000005
;
the alkyl, cycloalkyl, alkenyl, alkynyl, heterocycloalkyl, aryl or heteroaryl of Ar1 through Ar3 may be further substituted by R11;
R11 represents (C6-C30)aryl, (C3-C30)heteroaryl,
Figure PCTKR2011002293-appb-I000006
or
Figure PCTKR2011002293-appb-I000007
;
R1 and R2 independently represent hydrogen, deuterium, (C1-C30)alkyl, halogen, cyano, morpholino, thiomorpholino, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C7-C30)bicycloalkyl, adamantyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C1-C30)alkoxy, (C6-C30)aryloxy, (C3-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)arylthio, mono- or di(C1-C30)alkylamino, mono- or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, nitro or hydroxyl;
W represents -(CR15R16)a-, -(R15)C=C(R16)-, -N(R17)-, -S-, -O- or -Si(R18)(R19)-, wherein a represents an integer from 0 to 2;
R12 through R14 and R15 through R19 are the same as R1 and R2;
the alkyl, cycloalkyl, heterocycloalkyl, bicycloalkyl, adamantyl, alkenyl, alkynyl, aryl, alkoxy, aryloxy, heteroaryl, aralkyl, arylthio, alkylamino, arylamino, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R1 and R2, and the aryl or heteroaryl of R11 may be further substituted by one or more substituent(s) selected from the group consisting of (C1-C30)alkyl, halogen, cyano, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C7-C30)bicycloalkyl, adamantyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C6-C30)aryl substituted by carbazole, (C1-C30)alkoxy, (C6-C30)aryloxy, carbazole, (C3-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)arylthio, mono- or di(C1-C30)alkylamino, mono- or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, nitro and hydroxyl;
m and n independently represent an integer from 1 to 4; and
R1 and R2 may be identical or different.
In the present invention, "alkyl", "alkoxy" and other substituents containing "alkyl" moiety include both linear and branched species.
In the present invention, "aryl" means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring, including a plurality of aryl groups having single bond(s) therebetween. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto. The naphthyl includes 1-naphthyl and 2-naphthyl. The anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl. In the present invention, "heteroaryl" means an aryl group containing 1 to 4 heteroatom(s) selected from B, N, O, S, P(=O), Si and P as aromatic ring backbone atom(s), other remaining aromatic ring backbone atoms being carbon. It may be 5- or 6-membered monocyclic heteroaryl or polycyclic heteroaryl resulting from condensation with a benzene ring, and may be partially saturated. The heteroaryl also includes heteroaryl groups having single bond(s) therebetween.
The heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt. Specific examples include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, benzodioxolyl, etc., an N-oxide thereof (e.g., pyridyl N-oxide, quinolyl N-oxide, etc.), a quaternary salt thereof, etc., but are not limited thereto.
In the present invention, the alkyl moiety of "(C1-C30)alkyl, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyloxy, (C1-C30)alkylthio" or the like may have 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms. The aryl moiety of "(C6-C30)aryl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)aryloxy, (C6-C30)arylthio" or the like may have 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms. The heteroaryl of "(C3-C30)heteroaryl" may have 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms. The cycloalkyl of "(C3-C30)cycloalkyl" may have 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms. The alkenyl or alkynyl of "(C2-C30)alkenyl or alkynyl" may have 2 to 20 carbon atoms, more specifically 2 to 10 carbon atoms.
The R1 and R2 independently represent hydrogen, deuterium, (C1-C30)alkyl, halogen, cyano, morpholino, thiomorpholino, (C6-C30)aryl, (C3-C30)heteroaryl, (C6-C30)arylthio, mono- or di(C1-C30)alkylamino, mono- or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, nitro or hydroxyl, and the alkyl, aryl, heteroaryl, arylthio, alkylamino, arylamino, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R1 and R2 may be further substituted by one or more substituent(s) selected from the group consisting of (C1-C30)alkyl, halogen, (C6-C30)aryl, (C6-C30)aryl substituted by carbazole, (C1-C30)alkoxy, (C6-C30)aryloxy, carbazole, (C3-C30)heteroaryl, mono- or di(C1-C30)alkylamino, mono- or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl and tri(C6-C30)arylsilyl.
The Ar1 through Ar3 are independently selected from the following structures but are not limited thereto:
Figure PCTKR2011002293-appb-I000008
Figure PCTKR2011002293-appb-I000009
Figure PCTKR2011002293-appb-I000010
Figure PCTKR2011002293-appb-I000011
Figure PCTKR2011002293-appb-I000012
Figure PCTKR2011002293-appb-I000013
Figure PCTKR2011002293-appb-I000014
Figure PCTKR2011002293-appb-I000015
wherein
R21 represents hydrogen or R11; R22 represents R11; R11 is the same as defined in Chemical Formula 1; w represents an integer 1 or 2; x represents an integer from 1 to 5; y represents an integer from 1 to 3; and z represents an integer from 1 to 4.
More specifically, the Ar1 through Ar3 independently represent a substituent selected from following structures but are limited thereto:
Figure PCTKR2011002293-appb-I000016
Figure PCTKR2011002293-appb-I000017
Figure PCTKR2011002293-appb-I000018
Figure PCTKR2011002293-appb-I000019
Figure PCTKR2011002293-appb-I000020
Figure PCTKR2011002293-appb-I000021
Figure PCTKR2011002293-appb-I000022
Figure PCTKR2011002293-appb-I000023
Figure PCTKR2011002293-appb-I000024
Figure PCTKR2011002293-appb-I000025
Figure PCTKR2011002293-appb-I000026
Figure PCTKR2011002293-appb-I000027
Figure PCTKR2011002293-appb-I000028
Figure PCTKR2011002293-appb-I000029
Figure PCTKR2011002293-appb-I000030
Figure PCTKR2011002293-appb-I000031
Figure PCTKR2011002293-appb-I000032
The organic electroluminescent compound according to the present invention may be specifically exemplified as following compounds but the present invention is not limited thereto:
Figure PCTKR2011002293-appb-I000033
Figure PCTKR2011002293-appb-I000034
Figure PCTKR2011002293-appb-I000035
Figure PCTKR2011002293-appb-I000036
Figure PCTKR2011002293-appb-I000037
Figure PCTKR2011002293-appb-I000038
Figure PCTKR2011002293-appb-I000039
Figure PCTKR2011002293-appb-I000040
Figure PCTKR2011002293-appb-I000041
Figure PCTKR2011002293-appb-I000042
Figure PCTKR2011002293-appb-I000043
Figure PCTKR2011002293-appb-I000044
Figure PCTKR2011002293-appb-I000045
Figure PCTKR2011002293-appb-I000046
Figure PCTKR2011002293-appb-I000047
Figure PCTKR2011002293-appb-I000048
Figure PCTKR2011002293-appb-I000049
Figure PCTKR2011002293-appb-I000050
Figure PCTKR2011002293-appb-I000051
Figure PCTKR2011002293-appb-I000052
Figure PCTKR2011002293-appb-I000053
Provided is an organic electroluminescent device, which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compound(s) of Chemical Formula 1.
In the organic electroluminescent device, the organic layer comprises an electroluminescent layer including one or more phosphorescent dopant when one or more organic electroluminescent compounds of Chemical Formula 1 are used as the electroluminescent host. The dopant used in the organic electroluminescent device of the present invention is not particularly limited.
The organic electroluminescent device may comprise one or more organic electroluminescent compounds of Chemical Formula 1 and further comprises one or more amine compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds.
Also, in the organic electroluminescent device, the organic layer may further comprise one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s) as well as one or more organic electroluminescent compounds of Chemical Formula 1. The organic layer may comprise an electroluminescent layer and a charge generating layer.
In addition, the organic electroluminescent device is a white light-emitting organic electroluminescent device wherein the organic layer further comprises one or more organic electroluminescent layer(s) emitting blue, red or green light.
Since the organic electroluminescent compound according to the present invention is used as a host material of an organic electroluminescent material in an OLED device, it exhibits good luminous efficiency and excellent life property. Accordingly, it may be used to manufacture OLED devices having very superior operation life.
The present invention is further described with respect to organic electroluminescent compounds according to the present invention, processes for preparing the same, and luminescence properties of devices employing the same. However, the following examples are provided for illustrative purposes only and they are not intended to limit the scope of the present invention.
[Preparation Example 1] Preparation of Compound 2
Figure PCTKR2011002293-appb-I000054
Preparation of Compound A
After 1-phenylpyrrole (10g, 69.83mmol) was dissolved in THF (400mL), the mixture was cooled to 0℃, and NBS (18.6, 104.75mmol) was added thereto. After slowly raising the temperature to room temperature, the mixture was stirred for 12 hours and extracted with EA. After washing the reaction mixture with distilled water and NaCl solution, Compound A (15g, 71%) was obtained by column separation.
Preparation of Compound B
After 1-iodo-2-nitrobenzene (25g, 0.10mol) was dissolved in THF (500mL), the mixture was cooled to -78℃ and phenylmagnesium chloride(2M) (65mL, 0.13mol) was slowly added thereto. After slowly stirring the mixture at -78℃ for 1 hour, trimethylborate (16mL, 0.15mol) was added. After slowly raising the temperature to room temperature, the mixture was stirred for 12 hours. When the reaction was completed by adding 1M HCl (100mL) thereto, the mixture was extracted with EA and washed with distilled water and NaCl solution. After drying the reaction mixture with magnesium sulfate and performing distillation under reduced pressure, Compound B (15g, 89%) was obtained by recrystallizing the produced solid under the condition of MC:Hexane=1:10.
Preparation of Compound C
Compound A (5g, 16.61mmol), Compound B (6.9g, 41.53mmol), Pd(PPh3)4 (959mg, 0.83mmol), Na2CO3 (2M) (80mL), EtOH (60mL) and toluene (200mL) were added and stirred under reflux at 120℃ for 12 hours. After cooling the mixture to room temperature, the mixture was extracted with EA and washed with distilled water and NaCl solution. Compound C (6g, 93%) was obtained by column separation.
Preparation of Compound D
Compound C (5g, 12.97mmol) was added to triethylphosphite (50mL) and the mixture was stirred under reflux at 160℃ for 5 hours. After removing triethylphosphite by a distillation device, the mixture was extracted with EA and washed with distilled water. Compound D (2.8g, 67%) was obtained by column separation.
Preparation of Compound E
Compound D (5.0g, 15.55mmol), iodobenzene (1.7mL, 15.55mmol), CuI (4.4g, 23.33mmol), K2CO3 (4.3g, 31.11mmol) and quinoline (200mL) were mixed and stirred under reflux at 190℃ for 12 hours. After cooling the mixture to room temperature and performing distillation under reduced pressure, the mixture was extracted with MC and washed with distilled water. After drying the reaction mixture with magnesium sulfate and performing distillation under reduced pressure, Compound E (2.0g, 32%) was obtained by column separation.
Preparation of Compound 2
NaH(60% in mineral oil) (0.37g, 9.33mmol) was diluted with DMF (5mL). After Compound E (2.9g, 7.47mmol) was dissolved in DMF (20mL), the mixture was added to the diluted solution. The mixture was stirred at room temperature for 1 hour. After Compound F (2.0g, 7.47mmol) was dissolved in DMF (20mL), it was added to the mixture stirred at room temperature for 1 hour. After stirring the mixture for 4 hours at room temperature, distilled water (40mL) was added. After distilling the produced solid under reduced pressure, Target Compound 2 (2.0g, 42%) was obtained by recrystallizing the solid with EA.
[Preparation Example 2] Preparation of Compound 80
Figure PCTKR2011002293-appb-I000055
Preparation of Compound G
After 1-iodo-2-nitrobenzene (25g, 0.10mol) was dissolved in THF (500mL), the mixture was cooled to -78℃. Phenylmagnesium chloride(2M) (65mL, 0.13mol) was slowly added thereto. After stirring the mixture at -78℃ for 1 hour, trimethylborate (16mL, 0.15mol) was slowly added. After slowly heating the mixture to room temperature, the mixture was stirred for 12 hours. When the reaction was completed by adding 1M HCl (100mL), the mixture was extracted with EA and washed with distilled water and NaCl solution. After drying with magnesium sulfate and distillation under reduced pressure, Compound G (15g, 89%) was obtained by recrystallizing a produced solid under the condition of MC:Hexane=1:10.
Preparation of Compound H
2,5-dibromothiophen (5g, 20.66mmol), Compound G (8.6g, 51.66mmol), Pd(PPh3)4 (1.1g, 1.03mmol), Na2CO3 (2M) (80mL), EtOH (60mL) and toluene (200mL) were added and stirred under reflux at 120℃ for 12 hours. After cooling to room temperature, the mixture was extracted with EA and washed with distilled water and NaCl solution. Compound H (4g, 59%) was obtained by column separation.
Preparation of Compound I
Compound H (5g, 15.32mmol) was added to triethylphosphite (50mL) and stirred under reflux at 160℃ for 5 hours. After removing triethylphosphite by the distillation device, the mixture was extracted with EA and washed with distilled water. Compound I (2.5g, 62%) was obtained by column separation.
Preparation of Compound J
Compound I (5.0g, 19.05mmol), iodobenzene (3.8g, 19.05mmol), CuI (5.4g, 28.58mmol), K2CO3 (5.2g, 38.11mmol) and quinoline (200mL) were mixed and stirred under reflux at 190℃ for 12 hours. After cooling to room temperature, the mixture was distilled under reduced pressure, extracted with MC and washed with distilled water. After drying with magnesium sulfate and distillation under reduced pressure, Compound J (2.0g, 31%) was obtained by column separation.
Preparation of Compound 80
NaH(60% in mineral oil) (0.44g, 11.08mmol) was diluted with DMF (5mL). Compound J (3.0g, 8.86mmol) was dissolved in DMF (20mL) and the mixture was added to the diluted solution. After stirring the mixture at room temperature for 1 hour and dissolving Compound K (2.3g, 8.86mmol) in DMF (20mL), Compound K (2.3g, 8.86mmol)dissolved in DMF (20mL) was added to the mixture. The mixture was stirred at room temperature for 4 hours and added to distilled water (40mL) to produce a solid. Compound 80 (2.0g, 39%) was obtained by filtering the produced solid under reduced pressure and recrystallizing the solid with EA.
Organic electroluminescent compounds were prepared according to the procedure of Preparation Examples 1 and 2. 1H NMR and MS/FAB data of thus prepared organic electroluminescent compounds are given in Table 1.
Table 1
Comp. 1H NMR(CDCl3, 200 MHz) MS/FAB
found calculated
1 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(9H, m), 7.58(4H, m), 7.94(2H, m), 8.28(2H, m), 8.59(1H, s), 8.74(2H, m) 552.63 552.21
2 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(12H, m), 7.58(4H, m), 7.94(2H, m), 8.28(4H, m), 8.74(2H, m) 628.72 628.24
3 δ= 7.25(6H, m), 7.33(2H, m), 7.41~7.52(16H, m), 7.58(4H, m), 7.85(4H, m), 7.94(2H, m), 8.74(2H, m) 780.91 780.30
4 δ= 7.25(4H, m), 7.33(2H, m), 7.41~7.52(14H, m), 7.58(4H, m), 7.85(2H, m), 7.94(2H, m), 8.28(2H, m), 8.74(2H, m) 704.82 704.27
5 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.5(24H, m), 7.7(2H, m), 7.94(2H, m), 8.24(2H, m), 8.74(2H, m) 780.91 780.30
6 δ= 7.25(2H, m), 7.33(2H, m), 7.41(1H, m), 7.45~7.51(21H, m), 7.7~7.73(3H, m), 7.92~8(5H, m), 8.24(2H, m), 8.74(2H, m) 830.97 830.32
7 δ= 7.25(2H, m), 7.33~7.36(4H, m), 7.45~7.5(6H, m), 7.58(4H, m), 7.85(2H, m), 7.94(2H, m), 8.38(2H, m), 8.59(2H, m), 8.74(2H, m) 630.70 630.23
8 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(12H, m), 7.58(4H, m), 7.94(2H, m), 8.28(4H, m), 8.74(2H, m), 9.26(4H, m) 784.87 784.28
9 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(12H, m), 7.58(4H, m), 7.68(2H, m), 7.79(2H, m), 7.94(2H, m), 8.28(4H, m), 8.74(2H, m) 704.82 704.27
10 δ= 7.25~7.33(7H, m), 7.41~7.51(10H, m), 7.58~7.68(9H, m), 7.79(4H, m), 7.94(3H, m), 8.12(1H, m), 8.28(2H, m), 8.55(1H, m), 8.74(2H, m) 870.01 869.33
11 δ= 7.25~7.33(7H, m), 7.41~7.51(10H, m), 7.58~7.68(7H, m), 7.79(2H, m), 7.94(3H, m), 8.12(1H, m), 8.28(2H, m), 8.55(1H, m), 8.74(2H, m) 793.91 793.30
12 δ= 2.34(12H, s), 7.25~7.33(6H, m), 7.45~7.5(6H, m), 7.58~7.6(8H, m), 7.94(2H, m), 8.74(2H, m) 684.83 684.30
13 δ= 7.25(4H, m), 7.33(2H, m), 7.41~7.51(12H, m), 7.58(4H, m), 7.68(2H, m), 7.79~7.85(4H, m), 7.94(2H, m), 8.28(4H, m), 8.74(2H, m) 780.91 780.30
14 δ= 7.25(2H, m), 7.33~7.37(8H, m), 7.45~7.58(21H, m), 7.89~7.94(4H, m), 8.59(1H, s), 8.74(2H, m) 811.02 810.29
15 δ= 3.83(12H, s), 6.33(2H, m), 6.92(4H, m), 7.25(2H, m), 7.33(2H, m), 7.45~7.5(6H, m), 7.58(4H, m), 7.94(2H, m), 8.74(2H, m) 748.83 748.28
16 δ= 6.61(2H, m), 7.14~7.17(12H, m), 7.23~7.25(6H, m), 7.33(2H, m), 7.41~7.5(14H, m), 7.58(4H, m), 7.94(2H, m), 8.74(2H, m) 997.10 996.34
17 δ= 5.73(2H, m), 6.25(4H, m), 6.63(16H, m), 6.81(8H, m), 7.2~7.25(18H, m), 7.33(2H, m), 7.45~7.5(6H, m), 7.58(4H, m), 7.94(2H, m), 8.74(2H, m) 1297.55 1296.53
18 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(9H, m), 7.58(2H, m), 7.71(1H, m), 7.94(2H, m), 8.28(4H, m), 8.74(2H, m), 8.85(2H, m) 630.70 630.23
19 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(9H, m), 7.58(2H, m), 7.94(2H, m), 8.28(4H, m), 8.74(2H, m), 8.87(2H, m) 631.69 631.22
20 δ= 7.25(2H, m), 7.33(2H, m), 7.4~7.51(11H, m), 7.58(2H, m), 7.94(2H, m), 8.28(4H, m), 8.42(2H, m), 8.74(2H, m) 629.71 629.23
21 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(9H, m), 7.58(2H, m), 7.94(2H, m), 8.28(4H, m), 8.74(2H, m), 8.87(2H, m) 631.69 631.22
22 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(9H, m), 7.58(2H, m), 7.71(1H, m), 7.94(2H, m), 8.28(4H, m), 8.74(2H, m), 8.85(2H, m) 630.70 630.23
23 δ= 7.25(2H, m), 7.33(2H, m), 7.4~7.51(11H, m), 7.58(2H, m), 7.94(2H, m), 8.28(4H, m), 8.42(2H, m), 8.74(2H, m) 629.71 629.23
24 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(9H, m), 7.58(4H, m), 7.79(2H, m), 7.94~7.96(3H, m), 8.57(1H, m), 8.74(2H, m) 551.64 551.21
25 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(12H, m), 7.58(4H, m), 7.79(4H, m), 7.94(2H, m), 8.63(1H, s), 8.74(2H, m) 627.73 627.24
26 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.52(16H, m), 7.58(4H, m), 7.85(4H, m), 7.94(2H, m), 8.3(4H, m), 8.63(1H, s), 8.74(2H, m) 779.93 779.30
27 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.52(14H, m), 7.58(4H, m), 7.79~7.85(4H, m), 7.94(2H, m), 8.3(2H, m), 8.63(1H, s), 8.74(2H, m) 703.83 703.27
28 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.5(24H, m), 7.7~7.75(4H, m), 7.94(2H, m), 8.63(1H, s), 8.74(2H, m) 779.93 779.30
29 δ= 7.25(2H, m), 7.33(2H, m), 7.41(1H, m), 7.45~7.51(21H, m), 7.7~7.75(5H, m), 7.92~8(5H, m), 8.63(1H, s), 8.74(2H, m) 829.99 829.32
30 δ= 7.25(2H, m), 7.33~7.36(4H, m), 7.45~7.5(6H, m), 7.58(4H, m), 7.85(2H, m), 7.94(2H, m), 8.4(2H, m), 8.59(2H, m), 8.74(2H, m), 10.55(1H, s) 629.71 629.23
31 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(12H, m), 7.58(4H, m), 7.94(2H, m), 8.28(4H, m), 8.74(2H, m), 8.75(1H, s), 9.26(4H, m) 783.88 783.29
32 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(12H, m), 7.58(4H, m), 7.68(2H, m), 7.79(6H, m), 7.94(2H, m), 8.23(1H, s), 8.74(2H, m) 703.83 703.27
33 δ= 7.25~7.33(7H, m), 7.41~7.51(10H, m), 7.58~7.68(9H, m), 7.79(6H, m), 7.94(3H, m), 8.12(1H, m), 8.23(1H, s), 8.55(1H, m), 8.74(2H, m) 868.02 868.33
34 δ= 7.25~7.29(4H, m), 7.32(1H, s), 7.33(3H, m), 7.41~7.51(10H, m), 7.58~7.68(7H, m), 7.79(4H, m), 7.94(3H, m), 8.12(1H, m), 8.55(1H, m), 8.74(2H, m) 792.93 792.30
35 δ= 7.25(4H, m), 7.33(2H, m), 7.41~7.51(12H, m), 7.58(4H, m), 7.68(2H, m), 7.79~7.85(8H, m), 7.94(2H, m), 8.23(1H, s), 8.74(2H, m) 779.93 779.30
36 δ= 2.34(12H, s), 7.25~7.33(6H, m), 7.45~7.5(6H, m), 7.58~7.6(8H, m), 7.94(2H, m), 8.63(1H, s), 8.74(2H, m) 683.84 683.30
37 δ= 7.25(2H, m), 7.33~7.37(8H, m), 7.45~7.58(21H, m), 7.89~7.96(5H, m), 8.57(1H, m), 8.74(2H, m) 810.03 809.30
38 δ= 3.83(12H, s), 6.33(2H, m), 6.92(4H, m), 7.25(2H, m), 7.33(2H, m), 7.45~7.5(6H, m), 7.58(4H, m), 7.94(2H, m), 8.63(1H, s), 8.74(2H, m) 747.84 747.28
39 δ= 6.61(2H, m), 7.14~7.17(12H, m), 7.23~7.25(6H, m), 7.33(2H, m), 7.41~7.5(14H, m), 7.58(4H, m), 7.94(2H, m), 8.63(1H, s), 8.74(2H, m) 996.12 995.35
40 δ= 5.73(2H, m), 6.25(4H, m), 6.63(16H, m), 6.81(8H, m), 7.2~7.25(18H, m), 7.33(2H, m), 7.45~7.5(6H, m), 7.58(4H, m), 7.94(2H, m), 8.63(1H, s), 8.74(2H, m) 1296.56 1295.54
41 δ= 7.05(2H, m), 7.25(2H, m), 7.33(2H, m), 7.45~7.58(16H, m), 7.94(2H, m), 8.3(4H, m), 8.74(2H, m) 626.75 626.25
42 δ= 7.14(2H, m), 7.25(2H, m), 7.33(2H, m), 7.45~7.5(6H, m), 7.58(4H, m), 7.7(2H, m), 7.94(2H, m), 8.15(2H, m), 8.53(2H, m), 8.74(2H, m), 9.3(2H, m) 628.72 628.24
43 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(12H, m), 7.58(4H, m), 7.94(2H, m), 8.28(4H, m), 8.74(2H, m), 9.26(4H, m) 784.87 784.28
44 δ= 7.25(2H, m), 7.33(2H, m), 7.45~7.58(16H, m), 7.68(2H, m), 7.79(2H, m), 7.94(2H, m), 8.2(2H, m), 8.3(4H, m), 8.74(2H, m) 702.84 702.28
45 δ= 7.25(6H, m), 7.33(2H, m), 7.45~7.58(16H, m), 7.68(2H, m), 7.79(2H, m), 7.94(2H, m), 8.2(2H, m), 8.3(4H, m), 8.74(2H, m) 778.94 778.31
46 δ= 7.25~7.37(11H, m), 7.45~7.58(22H, m), 7.94(2H, m), 8.38~8.4(3H, m), 8.74(2H, m) 809.04 808.30
47 δ= 7.14(1H, m), 7.25(2H, m), 7.33(2H, m), 7.45~7.5(6H, m), 7.57~7.64(6H, m), 7.7(1H, m), 7.94(2H, m), 8.53(1H, m), 8.74(2H, m), 9.3(2H, m) 551.64 551.21
48 δ= 7.25(2H, m), 7.32~7.36(4H, m), 7.45~7.5(6H, m), 7.58(4H, m), 7.85(1H, m), 7.94(2H, m), 8.36(1H, m), 8.44(1H, m), 8.59(1H, m), 8.74(2H, m), 9.75(1H, m) 551.64 551.21
49 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(9H, m), 7.58(4H, m), 7.94(2H, m), 8.28(2H, m), 8.59(1H, s), 8.74(2H, m) 552.63 552.21
50 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(12H, m), 7.58(4H, m), 7.79(4H, m), 7.94(2H, m), 8.63(1H, s), 8.74(2H, m) 627.73 627.24
51 δ= 7.25(2H, m), 7.33(2H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.71(2H, m), 7.85(4H, m), 7.94(2H, m), 8.3(4H, m), 8.63(1H, s), 8.74(2H, m), 8.85(4H, m) 783.88 783.29
52 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.52(14H, m), 7.58(4H, m), 7.79~7.85(4H, m), 7.94(2H, m), 8.3(2H, m), 8.63(1H, s), 8.74(2H, m) 703.83 703.27
53 δ= 7.05(2H, m), 7.25(2H, m), 7.33(2H, m), 7.41~7.51(24H, m), 7.94(2H, m), 8.21~8.26(4H, m), 8.74(2H, m) 778.94 778.31
54 δ= 7.25(2H, m), 7.33(2H, m), 7.41(1H, m), 7.45~7.51(21H, m), 7.7~7.73(3H, m), 7.92~8(5H, m), 8.24(2H, m), 8.74(2H, m) 830.97 830.32
55 δ= 7.25(2H, m), 7.33~7.36(4H, m), 7.45~7.5(6H, m), 7.58(4H, m), 7.85(2H, m), 7.94(2H, m), 8.38(2H, m), 8.59(2H, m), 8.74(2H, m) 630.70 630.23
56 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(12H, m), 7.58(4H, m), 7.94(2H, m), 8.28(4H, m), 8.74(2H, m), 9.26(4H, m) 784.87 784.28
57 δ= 7.25(2H, m), 7.33(2H, m), 7.4~7.41(6H, m), 7.51(4H, m), 7.68(2H, m), 7.79(2H, m), 7.94(2H, m), 8.28(4H, m), 8.42(4H, m), 8.74(2H, m) 706.79 706.26
58 δ= 7.25~7.33(7H, m), 7.41~7.51(10H, m), 7.58~7.68(9H, m), 7.79(4H, m), 7.94(3H, m), 8.12(1H, m), 8.28(2H, m), 8.55(1H, m), 8.74(2H, m) 870.01 869.33
59 δ= 7.25~7.33(7H, m), 7.41~7.51(10H, m), 7.58~7.68(7H, m), 7.79(2H, m), 7.94(3H, m), 8.12(1H, m), 8.28(2H, m), 8.55(1H, m), 8.74(2H, m) 793.91 793.30
60 δ= 7.25(4H, m), 7.33(2H, m), 7.41~7.51(12H, m), 7.58(4H, m), 7.68(2H, m), 7.79~7.85(4H, m), 7.94(2H, m), 8.28(4H, m), 8.74(2H, m) 780.91 780.30
61 δ= 2.34(24H, s), 7.25~7.33(8H, m), 7.45~7.5(3H, m), 7.58~7.6(10H, m), 7.94(2H, m), 8.74(2H, m) 896.09 895.41
62 δ= 7.25(2H, m), 7.33~7.37(8H, m), 7.45~7.58(21H, m), 7.89~7.94(4H, m), 8.59(1H, s), 8.74(2H, m) 811.02 810.29
63 δ= 3.83(12H, s), 6.33(2H, m), 6.92(4H, m), 7.25(2H, m), 7.33(2H, m), 7.45~7.5(6H, m), 7.58(4H, m), 7.94(2H, m), 8.74(2H, m) 748.83 748.28
64 δ= 6.61(2H, m), 7.14~7.17(12H, m), 7.23~7.25(6H, m), 7.33(2H, m), 7.41~7.5(14H, m), 7.58(4H, m), 7.94(2H, m), 8.74(2H, m) 997.10 996.34
65 δ= 5.73(2H, m), 6.25(4H, m), 6.63(16H, m), 6.81(8H, m), 7.2~7.25(18H, m), 7.33(2H, m), 7.45~7.5(6H, m), 7.58(4H, m), 7.94(2H, m), 8.74(2H, m) 1297.55 1296.53
66 δ= 7.25(2H, m), 7.33~7.51(12H, m), 7.58~7.59(4H, m), 7.83(1H, m), 7.94~8(5H, m), 8.28(4H, m), 8.74(2H, m) 678.78 678.25
67 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(9H, m), 7.58~7.6(3H, m), 7.78(1H, m), 7.91~7.98(4H, m), 8.06(1H, m), 8.28(4H, m), 8.38(1H, m), 8.74(2H, m) 679.77 679.25
68 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(9H, m), 7.58~7.59(5H, m), 7.68~7.79(5H, m), 7.92~8(5H, m), 8.28(4H, m), 8.74(2H, m) 754.88 754.28
69 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(9H, m), 7.58~7.59(4H, m), 7.9~8(7H, m), 8.28~8.38(6H, m), 8.74(2H, m), 8.85(1H, m) 755.87 755.28
70 δ= 7.25~7.33(5H, m), 7.41~7.51(13H, m), 7.58~7.63(6H, m), 7.94~7.98(4H, m), 8.12(1H, m), 8.28(4H, m), 8.74(2H, m) 793.91 793.30
71 δ= 7.25(3H, m), 7.33(3H, m), 7.41~7.51(12H, m), 7.58(6H, m), 7.69(1H, m), 7.77(1H, m), 7.87(1H, m), 7.94(3H, m), 8.28(2H, m), 8.55(1H, m), 8.74(2H, m) 793.91 793.30
72 δ= 7.41~7.52(22H, m), 7.58(4H, m), 7.77(2H, m), 8(2H, m), 8.18(2H, m), 8.28(4H, m) 780.91 780.30
73 δ= 7(2H, m), 7.26(2H, m), 7.41~7.51(14H, m), 7.58(4H, m), 8.03(2H, m), 8.28(6H, m), 8.5(2H, m), 8.69(2H, m) 782.89 782.29
74 δ= 7.31(2H, m), 7.41~7.51(12H, m), 7.58(4H, m), 7.77(2H, m), 8(2H, m), 8.18(2H, m), 8.28(4H, m), 8.86(4H, m) 784.87 784.28
75 δ= 7.41~7.51(12H, m), 7.58(4H, m), 7.77(2H, m), 8(2H, m), 8.18(2H, m), 8.28(4H, m), 8.71(4H, m) 786.84 786.27
76 δ= 7.06(2H, m), 7.41~7.51(12H, m), 7.58(4H, m), 7.92(2H, m), 8.22~8.28(6H, m) 664.70 664.22
77 δ= 7.41~7.51(12H, m), 7.58(4H, m), 8.08(2H, m), 8.2(2H, m), 8.28(4H, m), 9.72(2H, m) 718.72 718.21
78 δ= 7.33(2H, m), 7.41~7.51(12H, m), 7.58(4H, m), 7.8(2H, m), 8.12(2H, m), 8.28(4H, m) 678.74 678.23
79 δ= 5.35(2H, s), 6.38(2H, m), 7.26(2H, m), 7.41~7.51(12H, m), 7.58(4H, m), 7.85(2H, m), 8.28(4H, m) 660.72 660.23
80 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(9H, m), 7.58(2H, m), 7.94(2H, m), 8.28(4H, m), 8.43(2H, m) 569.68 569.17
81 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(9H, m), 7.58(2H, m), 7.79(4H, m), 7.94(2H, m), 8.43(2H, m), 8.63(1H, s) 568.69 568.17
82 δ= 7.25(2H, m), 7.33(2H, m), 7.4~7.41(4H, m), 7.51(4H, m), 7.79(4H, m), 7.94(2H, m), 8.42~8.43(4H, m), 8.63(1H, s) 569.68 569.17
83 δ= 7.25(2H, m), 7.33(2H, m), 7.41(2H, m), 7.51(4H, m), 7.71(1H, m), 7.79(4H, m), 7.94(2H, m), 8.43(2H, m), 8.63(1H, s), 8.85(2H, m) 570.67 570.16
84 δ= 7.25(2H, m), 7.33(2H, m), 7.41(2H, m), 7.51(4H, m), 7.94(2H, m), 8.28(4H, m), 8.43(2H, m), 8.87(2H, m) 572.64 572.15
85 δ= 1.73(4H, m), 1.88(4H, m), 2.72(1H, m), 3.64(1H, m), 7.25(2H, m), 7.33(2H, m), 7.41(2H, m), 7.51(4H, m), 7.94(2H, m), 8.28(4H, m), 8.74(2H, m), 8.87(4H, m) 716.79 716.29
86 δ= 1.94(4H, m), 2.96(4H, m), 3.7(1H, m), 7.25(2H, m), 7.33(2H, m), 7.41(2H, m), 7.51(4H, m), 7.71(2H, m), 7.79(4H, m), 7.85(1H, s), 7.94(2H, m), 8.74(2H, m), 8.85(4H, m) 714.82 714.30
87 δ= 5.6(1H, m), 6.9(1H, m), 7.25(2H, m), 7.33(2H, m), 7.41(2H, m), 7.51(4H, m), 7.94(2H, m), 8.28(4H, m), 8.74(2H, m), 8.87(4H, m) 660.69 660.22
88 δ= 7.25(2H, m), 7.33(2H, m), 7.41(2H, m), 7.51(4H, m), 7.71(2H, m), 7.79(4H, m), 7.94(2H, m), 8.61(1H, s), 8.74(2H, m), 8.85(4H, m) 655.71 655.22
89 δ= 5.11(2H, m), 7.25(2H, m), 7.33(2H, m), 7.41(2H, m), 7.51(4H, m), 7.71(2H, m), 7.79(4H, m), 7.94(2H, m), 8.39(1H, s), 8.74(2H, m), 8.85(4H, m) 645.71 645.24
90 δ= 1.35(18H, s), 7.11(2H, m), 7.41~7.51(12H, m), 7.58(4H, m), 7.79(4H, m), 7.86(2H, m), 8.63(1H, s), 8.95(2H, m) 739.95 739.37
91 δ= 3.18(8H, m), 3.65(8H, m), 6.06(2H, m), 7.41~7.51(12H, m), 7.58(4H, m), 7.76(4H, m), 8.28(4H, m) 798.93 798.34
92 δ= 7.02(2H, m), 7.19~7.25(6H, m), 7.41~7.51(18H, m), 7.58(4H, m), 7.74(2H, m), 8.28(4H, m) 845.04 844.24
93 δ= 5.93(1H, m), 6.63(4H, m), 6.81(2H, m), 7.2~7.25(5H, m), 7.33(1H, m), 7.41~7.51(12H, m), 7.58~7.63(5H, m), 7.69(1H, m), 7.94(1H, m), 8.28(4H, m), 8.74(1H, m) 795.93 795.31
94 δ= 0.25(18H, s), 7.3(2H, m), 7.41~7.51(12H, m), 7.58(4H, m), 7.77(2H, m), 7.92(2H, m), 8.28(4H, m) 773.08 772.32
95 δ= 7.25(1H, m), 7.33(1H, m), 7.36(1H, m), 7.37~7.46(31H, m), 7.83(1H, m), 7.94(1H, m), 8.04(1H, m), 8.28(4H, m), 8.74(1H, m) 887.11 886.32
96 δ= 1.72(12H, s), 7.25~7.38(8H, m), 7.45~7.63(14H, m), 7.77(2H, m), 7.87~7.94(6H, m), 8.74(2H, m) 861.04 860.36
97 δ= 7.25(3H, m), 7.33(3H, m), 7.41~7.51(9H, m), 7.58~7.6(5H, m), 7.78(1H, m), 7.94~7.98(4H, m), 8.22~8.28(3H, m), 8.35(1H, s), 8.55(1H, m), 8.74(2H, m) 768.86 768.27
98 δ= 7.06(1H, m), 7.25(2H, m), 7.33(2H, m), 7.41~7.51(9H, m), 7.58~7.67(8H, m), 7.92~7.94(3H, m), 8.16(1H, m), 8.22~8.28(3H, m), 8.54(1H, m), 8.74(2H, m) 785.87 785.27
99 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(9H, m), 7.58(2H, m), 7.94(2H, m), 8.28(4H, m), 8.43(2H, m) 553.61 553.19
100 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.51(9H, m), 7.58(2H, m), 7.79(4H, m), 7.94(2H, m), 8.43(2H, m), 8.63(1H, s) 552.62 552.20
101 δ= 7.25(2H, m), 7.33(2H, m), 7.37~7.46(22H, m), 7.76(1H, m), 7.89~7.96(4H, m), 8.43(2H, m), 8.57(1H, m) 734.92 734.25
102 δ= 7.25(2H, m), 7.33(2H, m), 7.41~7.58(9H, m), 7.68(2H, m), 7.79(4H, m), 7.94(2H, m), 8.43(2H, m), 8.54(1H, m) 552.62 552.20
[Examples 1-9] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
An OLED device was manufactured using the electroluminescent material according to the present invention. First, a transparent electrode ITO thin film (15 Ω/□) obtained from a glass for OLED (produced by Samsung Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
Then, an ITO substrate was equipped in a substrate folder of a vacuum vapor deposition apparatus, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum vapor deposition apparatus, which was then ventilated up to 10-6 torr of vacuum in the chamber. Then, electric current was applied to the cell to evaporate 2-TNATA, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate. Then, N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell of the vacuum vapor deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
The compounds purified by vacuum sublimation at 10-6torr (e.g., Compound 2, 9, 18, 25, 37, 41, 50, 70 or 95) were placed in a cell of a vacuum vapor deposition apparatus as a host, and an electroluminescent dopant (e.g., (piq)2Ir(acac) [bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate]) was placed in another cell as a dopant. The two materials were evaporated at different rates such that an electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer through doping at 4 to 20 wt%.
Subsequently, tris(8-hydroxyquinoline)-aluminum(III) (Alq) was vapor-deposited with a thickness of 20 nm as an electron transport layer on the electroluminescent layer. Then, after vapor-depositing lithium quinolate (Liq) of a following structure with a thickness of 1 to 2 nm as an electron injection layer, an Al cathode having a thickness of 150 nm was formed using another vacuum vapor deposition apparatus to manufacture an OLED.
[Comparative Example 1] Manufacture of OLED device using conventional luminescent material
An OLED was manufactured in the same manner as that of Example 1 except that 4,4'-bis(carbazol-9-yl)biphenyl (CBP) instead of the electroluminescent compounds of the present invention was used as a host material at another cell of the vacuum vapor deposition apparatus after forming the hole injection layer and the hole transport layer.
[Comparative Example 2] Manufacture of OLED device using conventional luminescent material
An OLED was manufactured in the same manner as that of Example 1 except that 4,4'-bis(carbazol-9-yl)biphenyl (CBP) instead of the compounds of the present invention as a host material at one cell of the vacuum vapor deposition apparatus and Bis(2-methyl-8-quinolinato)(p-phenyl-phenolato)aluminum(III) (BAlq) as a hole blocking layer were used.
The driving voltage and the luminous efficiencies of the OLED comprising the organic electroluminescent compound according to the present invention (Examples 1 to 9) or the conventional EL compounds (Comparative Examples 1 and 2) were measured at 1,000 cd/m2, respectively, and the results are shown in Table 2.
Table 2
Host material Luminous material Hole blocking layer @1,000cd/m2 color
Driving voltage(V) Luminous efficiency(cd/A)
Example 1 Compound 2 (piq)2Ir(acac) - 6.5 6.7 red
Example 2 Compound 9 (piq)2Ir(acac) - 5.3 7.5 red
Example 3 Compound 18 (piq)2Ir(acac) - 5.8 6.4 red
Example 4 Compound 25 (piq)2Ir(acac) - 6.3 7.3 red
Example 5 Compound 37 (piq)2Ir(acac) - 7.3 7.1 red
Example 6 Compound 41 (piq)2Ir(acac) - 7.0 6.9 red
Example 7 Compound 50 (piq)2Ir(acac) - 6.7 6.3 red
Example 8 Compound 70 (piq)2Ir(acac) - 6.0 7.6 red
Example 9 Compound 95 (piq)2Ir(acac) - 6.8 8.5 red
Comparative Example 1 CBP (piq)2Ir(acac) - 7.5 6.5 red
Comparative Example 2 CBP (piq)2Ir(acac) BALq 7.5 2.6 red
As shown in Table 2, the organic electroluminescent compounds according to the present invention as a red light emitting material have luminous properties similar to or superior to the conventional material.
In a conventional device stricture, the device using the organic electroluminescent compound according to the present invention as a host material without using a hole blocking layer has excellent luminescent efficiency, drops driving voltage, and increases power efficiency, thereby reducing power consumption.
Since the organic electroluminescent compound according to the present invention is used as a host material of an organic electroluminescent material in an OLED device, it exhibits good luminous efficiency and excellent life property. Accordingly, it may be used to manufacture OLED devices having very superior operation life.

Claims (9)

  1. An organic electroluminescent compound represented by Chemical Formula 1:
    [Chemical Formula 1]
    Figure PCTKR2011002293-appb-I000056
    wherein
    X represents N(Ar3), S or O;
    Ar1 through Ar3 independently represent (C1-C30)alkyl, (C3-C30)cycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, 5- to 7-membered heterocycloalkyl containing one or more nitrogen atom(s), (C6-C30)aryl, (C3-C30)heteroaryl,
    Figure PCTKR2011002293-appb-I000057
    or
    Figure PCTKR2011002293-appb-I000058
    ;
    the alkyl, cycloalkyl, alkenyl, alkynyl, heterocycloalkyl, aryl or heteroaryl of Ar1 through Ar3 may be further substituted by R11;
    R11 represents (C6-C30)aryl, (C3-C30)heteroaryl,
    Figure PCTKR2011002293-appb-I000059
    or
    Figure PCTKR2011002293-appb-I000060
    ;
    R1 and R2 independently represent hydrogen, deuterium, (C1-C30)alkyl, halogen, cyano, morpholino, thiomorpholino, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C7-C30)bicycloalkyl, adamantyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C1-C30)alkoxy, (C6-C30)aryloxy, (C3-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)arylthio, mono- or di(C1-C30)alkylamino, mono- or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, nitro or hydroxyl;
    W represents -(CR15R16)a-, -(R15)C=C(R16)-, -N(R17)-, -S-, -O- or -Si(R18)(R19)-, wherein a represents an integer from 0 to 2;
    R12 through R14 and R15 through R19 are the same as R1 and R2;
    the alkyl, cycloalkyl, heterocycloalkyl, bicycloalkyl, adamantyl, alkenyl, alkynyl, aryl, alkoxy, aryloxy, heteroaryl, aralkyl, arylthio, alkylamino, arylamino, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R1 and R2, and the aryl or heteroaryl of R11 may be further substituted by one or more substituent(s) selected from the group consisting of (C1-C30)alkyl, halogen, cyano, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C7-C30)bicycloalkyl, adamantyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C6-C30)aryl substituted by carbazole, (C1-C30)alkoxy, (C6-C30)aryloxy, carbazole, (C3-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)arylthio, mono- or di(C1-C30)alkylamino, mono- or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, nitro and hydroxyl;
    m and n independently represent an integer from 1 to 4; and
    R1 and R2 may be identical or different.
  2. The organic electroluminescent compound according to claim 1, wherein Ar1 through Ar3 are independently selected from the following structures:
    Figure PCTKR2011002293-appb-I000061
    Figure PCTKR2011002293-appb-I000062
    Figure PCTKR2011002293-appb-I000063
    Figure PCTKR2011002293-appb-I000064
    Figure PCTKR2011002293-appb-I000065
    Figure PCTKR2011002293-appb-I000066
    Figure PCTKR2011002293-appb-I000067
    Figure PCTKR2011002293-appb-I000068
    wherein
    R21 represents hydrogen or R11; R22 represents R11; R11 is the same as defined in claim 1; w represents an integer 1 or 2; x represents an integer from 1 to 5; y represents an integer from 1 to 3; and z represents an integer from 1 to 4.
  3. The organic electroluminescent compound according to claim 1, wherein R1 and R2 independently represent hydrogen, deuterium, (C1-C30)alkyl, halogen, cyano, morpholino, thiomorpholino, (C6-C30)aryl, (C3-C30)heteroaryl, (C6-C30)arylthio, mono- or di(C1-C30)alkylamino, mono- or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, nitro or hydroxyl, and the alkyl, aryl, heteroaryl, arylthio, alkylamino, arylamino, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R1 and R2 may be further substituted by one or more substituent(s) selected from the group consisting of (C1-C30)alkyl, halogen, (C6-C30)aryl, (C6-C30)aryl substituted by carbazole, (C1-C30)alkoxy, (C6-C30)aryloxy, carbazole, (C3-C30)heteroaryl, mono- or di(C1-C30)alkylamino, mono- or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl and tri(C6-C30)arylsilyl.
  4. An organic electroluminescent device comprising the organic electroluminescent compound according to any of claims 1 to 3.
  5. The organic electroluminescent device according to claim 4, which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compound(s) according to any one of claims 1 to 3 and one or more phosphorescent dopant(s).
  6. The organic electroluminescent device according to claim 5, wherein the organic layer further comprises one or more amine compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds.
  7. The organic electroluminescent device according to claim 5, wherein the organic layer further comprises one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s).
  8. The organic electroluminescent device according to claim 5, wherein the organic layer comprises an electroluminescent layer and a charge generating layer.
  9. The organic electroluminescent device according to claim 5, which is a white light-emitting organic electroluminescent device wherein the organic layer further comprises one or more organic electroluminescent layer(s) emitting blue, red or green light.
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