WO2012039561A1 - Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique l'utilisant - Google Patents
Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique l'utilisant Download PDFInfo
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- WO2012039561A1 WO2012039561A1 PCT/KR2011/006855 KR2011006855W WO2012039561A1 WO 2012039561 A1 WO2012039561 A1 WO 2012039561A1 KR 2011006855 W KR2011006855 W KR 2011006855W WO 2012039561 A1 WO2012039561 A1 WO 2012039561A1
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- 0 CCC(NC([C@]1C=CO)C=*)=C1c([n](*)c1c2CCC=C1)c2C#C Chemical compound CCC(NC([C@]1C=CO)C=*)=C1c([n](*)c1c2CCC=C1)c2C#C 0.000 description 9
- GWWWCWGULSWMGY-UHFFFAOYSA-N Brc1cccc(-[n]2c3ccc(c4ccccc4[o]4)c4c3c3c2cccc3)c1 Chemical compound Brc1cccc(-[n]2c3ccc(c4ccccc4[o]4)c4c3c3c2cccc3)c1 GWWWCWGULSWMGY-UHFFFAOYSA-N 0.000 description 1
- LGURBQLNAWJNDU-UHFFFAOYSA-N CC(C)(c(c(-c1c2)c3)ccc3-c3ccccc3)c1cc1c2c2ccccc2[n]1-c1nc(-c(cc2)cc3c2c(cccc2)c2c2c3cccc2)ccn1 Chemical compound CC(C)(c(c(-c1c2)c3)ccc3-c3ccccc3)c1cc1c2c2ccccc2[n]1-c1nc(-c(cc2)cc3c2c(cccc2)c2c2c3cccc2)ccn1 LGURBQLNAWJNDU-UHFFFAOYSA-N 0.000 description 1
- KAXUPYUTISDQCE-UHFFFAOYSA-N CC(C1)C=Cc2c1[s]c1c2ccc2c1c(cccc1)c1[n]2-c1nc(-c(cc2)cc3c2c(cccc2)c2c2ccccc32)ccn1 Chemical compound CC(C1)C=Cc2c1[s]c1c2ccc2c1c(cccc1)c1[n]2-c1nc(-c(cc2)cc3c2c(cccc2)c2c2ccccc32)ccn1 KAXUPYUTISDQCE-UHFFFAOYSA-N 0.000 description 1
- ORPVVAKYSXQCJI-UHFFFAOYSA-N [O-][N+](c1ccccc1Br)=O Chemical compound [O-][N+](c1ccccc1Br)=O ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 1
- QXKVVKXZVVOXEN-UHFFFAOYSA-N c(cc1)cc(c2c3ccc4c2[o]c2ccccc42)c1[n]3-c1cc(-c2ccc(c3ccccc3c3ccccc33)c3c2)ccc1 Chemical compound c(cc1)cc(c2c3ccc4c2[o]c2ccccc42)c1[n]3-c1cc(-c2ccc(c3ccccc3c3ccccc33)c3c2)ccc1 QXKVVKXZVVOXEN-UHFFFAOYSA-N 0.000 description 1
- ZHUCLPQWHVIRAG-UHFFFAOYSA-N c(cc1)ccc1-[n]1c(c(c2c3cccc2)c(cc2)[n]3-c(cc3)ccc3-c3cc(-c4cc5c(cccc6)c6c(cccc6)c6c5cc4)ccc3)c2c2ccccc12 Chemical compound c(cc1)ccc1-[n]1c(c(c2c3cccc2)c(cc2)[n]3-c(cc3)ccc3-c3cc(-c4cc5c(cccc6)c6c(cccc6)c6c5cc4)ccc3)c2c2ccccc12 ZHUCLPQWHVIRAG-UHFFFAOYSA-N 0.000 description 1
- XYZGAMBQUKTSIJ-UHFFFAOYSA-N c(cc12)ccc1[nH]c(cc1)c2c2c1c(cccc1)c1[o]2 Chemical compound c(cc12)ccc1[nH]c(cc1)c2c2c1c(cccc1)c1[o]2 XYZGAMBQUKTSIJ-UHFFFAOYSA-N 0.000 description 1
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Definitions
- the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device including the same.
- electroluminescent (EL) devices which are self-emissive display devices, are advantageous in that they provide wide viewing angle, superior contrast and a fast response rate.
- EL electroluminescent
- Eastman Kodak first developed an organic EL device using a low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer [ Appl. Phys. Lett. 51, 913, 1987].
- 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.
- KR Patent Publication No. 2010-0056490 discloses a compound for organic electroluminescent materials in which triphenylene is substituted for carbazole, dibenzofuran, dibenzothiophene, etc.
- the above-mentioned document KR2010-0056490 does not disclose a compound wherein triphenylene is linked to a 5 membered-heteroaryl group fused with the rings including benzothiophene, indole, indene and benzofuran at the carbazole.
- an 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 material.
- Another object of the present invention is to provide an organic electroluminescent device having high efficiency and a long life using the organic electroluminescent compound as an electroluminescent material.
- organic electroluminescent compound represented by Chemical Formula 1 below, and an organic electroluminescent device using the same.
- the organic electroluminescent compound according to the present invention may be used to manufacture an OLED device having very superior operation life and consuming less power due to improved power efficiency.
- ring B represents ;
- X 1 through X 4 independently represent CR 3 or N;
- Y 1 and Y 2 independently represent a single bond, -O-, -S-, -C(R 11 )(R 12 )-, -Si(R 13 )(R 14 )- or -N(R 15 )-, except for a case where both Y 1 and Y 2 are a single bond;
- R 1 through R 3 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C6-C30)ar(C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyls, 5- to 7-membered heterocycloalkyl fused with substituted or unsubstituted one or more aromatic rings, (C3-C30)cycloalkyl fused with substituted or unsubstituted one or more aromatic rings, -NR 16 R
- R 11 through R 22 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl or substituted or unsubstituted (C3-C30)cycloalkyl, or they may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and a carbon atom of the alicyclic ring and the monocyclic or polycyclic aromatic ring may be substituted with one or more heteroatoms selected from the group consisting of N, O and S
- L 1 represents a single bond, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (C2-C30)heteroarylene, substituted or unsubstituted (C3-C30)cycloalkylene, -L 2 -L 3 - or -L 3 -L 2 -;
- L 2 represents substituted or unsubstituted (C6-C30)arylene
- L 3 represents substituted or unsubstituted (C2-C30)heteroarylene
- Ar 1 and Ar 2 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C2-C30)heteroaryl;
- o represents an integer of 1 to 4, and when o is an integer of 2 or greater, each of R 1 may be identical to or different from each other;
- p represents an integer of 1 or 2, and when p represents 2, each of R 2 may be identical to or different from each other;
- alkyl As described herein, “alkyl”, “alkoxy” and other substituents containing the “alkyl” moiety include both linear and branched species, and the “cycloalkyl” includes polycyclic hydrocarbon ring such as substituted or unsubstituted adamantyl or substituted or unsubstituted (C7-C30)bicycloalkyl as well as a monocyclic hydrocarbon ring.
- 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, and even further includes a structure where a plurality of aryls are linked by single bond(s). Specific examples thereof include phenyl, naphthyl, biphenyl, terphenyl, 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
- the phenanthryl includes 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl and 9-phenanthryl
- the naphthacenyl includes 1-naphthacenyl, 2-naphthacenyl and 9-naphthacenyl.
- the pyrenyl includes 1-pyrenyl, 2-pyrenyl and 4-pyrenyl
- the biphenyl includes 2-biphenyl, 3-biphenyl and 4-biphenyl
- the terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl
- the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
- heteroaryl includes a structure where one or more heteroaryls are linked by single bonds.
- the heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, N- oxide or quaternary salt.
- Specific examples thereof include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, or the like, polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazo
- the pyrrolyl includes 1-pyrrolyl, 2-pyrrolyl and 3-pyrrolyl; the pyridyl includes 2-pyridyl, 3-pyridyl and 4-pyridyl; the indolyl includes 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl and 7-indolyl; the isoindolyl includes 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl and 7-isoindolyl; the furyl includes 2-furyl and 3-furyl; the benzofuranyl includes 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl and 7-benzofuranyl; the isobenzofur
- (C1-C30)alkyl includes (C1-C20)alkyl or (C1-C10)alkyl
- (C6-C30)aryl includes (C6-C20)aryl
- (C2-C30)heteroaryl includes (C2-C20)heteroaryl
- (C3-C30)cycloalkyl includes (C3-C20)cycloalkyl or (C3-C7)cycloalkyl.
- (C2-C30)alkenyl or alkynyl includes (C2-C20)alkenyl or alkynyl, or (C2-C10)alkenyl or alkynyl.
- each substituent of the R 1 through R 3 , L 1 , L 2 , L 3 , Ar 1 , Ar 2 and R 11 through R 22 may be further substituted by one or more substituent(s) selected from the group consisting of deuterium, halogen, (C1-C30)alkyl, halogen-substituted (C1-C30)alkyl, (C6-C30)aryl, (C2-C30)heteroaryl, (C6-C30)alkyl-substituted (C2-C30)heteroaryl, (C6-C30)aryl-substituted (C2-C30)heteroaryl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (
- Chemical Formula 1 may be selected from the following structures, but is not limited thereto.
- R 1 , R 2 , R 11 through R 15 , o and p are the same as defined in Chemical Formula 1.
- X 1 through X 4 independently represent N or CR 3 ;
- Y 1 and Y 2 independently represent a single bond, -O-, -S-, -C(R 11 R 12 )- or -N(R 15 )-, except for a case where both Y 1 and Y 2 are a single bond;
- L 1 represents a single bond, phenylene, naphthalene, biphenylene, 9,9-diphenylfluorenylene, 9,9-dimethylfluorenylene, dibenzothiophene, dibenzofuran or spirofluorene;
- Ar 1 and Ar 2 independently represent hydrogen, phenyl, biphenyl, naphthyl, 9,9-diphenylfluorenyl, 9,9-dimethylfluorenyl, fluoranthenyl, pyridyl, N-phenylcarbazolyl, dibenzothiophene or dibenzofuran, and the phen
- organic electroluminescent compound according to the present invention may be exemplified by the following compounds, which are not intended to limit the present invention.
- organic electroluminescent compound according to the present invention may be prepared as shown, for example, Scheme 1 below, but 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 compounds represented by Chemical Formula 1.
- the organic layer includes an electroluminescent layer, and the organic electroluminescent compound of Chemical Formula 1 may be used as a host in the electroluminescent layer. Also, the compound of Chemical Formula 1 may be used after the addition of other host materials.
- the organic electroluminescent compound of Chemical Formula 1 when used as a host, one or more phosphorescent dopant(s) is included.
- the phosphorescent dopant applied to the organic electroluminescent device according to the present invention is not specifically limited, but may be selected from among compounds represented by Chemical Formula 2 below.
- M 1 is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16 of the Periodic table, and ligands L 101 , L 102 and L 103 are independently selected from the following structures:
- R 201 through R 203 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkyl-substituted or unsubstituted (C6-C30)aryl or halogen;
- R 204 through R 219 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, SF 5 , substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl,
- R 220 through R 223 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, or (C1-C30)alkyl-substituted or unsubstituted (C6-C30)aryl;
- R 224 and R 225 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl or halogen, or R 224 and R 225 may be linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
- R 226 represents substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, or halogen;
- R 227 through R 229 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or halogen;
- Q represents , or ;
- R 231 through R 242 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkoxy, halogen, substituted or unsubstituted (C6-C30)aryl, cyano or substituted or unsubstituted (C3-C30)cycloalkyl, or they may be linked to an adjacent substituent via alkylene or alkenylene to form a spiro ring or a fused ring, or may be linked to R 207 or R 208 via alkylene or alkenylene to form a saturated or unsaturated fused ring.
- the dopant compound of Chemical Formula 2 may be exemplified by the following compounds, but is not limited thereto.
- the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds, at the same time.
- the arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
- the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, 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).
- the organic layer may include an electroluminescent layer and a charge generating layer.
- the organic layer may include, in addition to the organic electroluminescent compound of Chemical Formula 1, one or more organic electroluminescent layer(s) emitting blue, green or red light at the same time in order to embody a white-emitting organic electroluminescent device.
- the compounds emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
- a layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a metal chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. Operation stability may be attained therefrom.
- the chalcogenide may be, for example, SiO x (1 ⁇ x ⁇ 2), AlO x (1 ⁇ x ⁇ 1.5), SiON, SiAlON, etc.
- the metal halide may be, for example, LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.
- the metal oxide may be, for example, Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
- the organic electroluminescent device it is also preferable to arrange on at least one surface of the pair of electrodes thus manufactured a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant.
- a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant.
- the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to an electroluminescent medium are facilitated.
- the hole transport compound is oxidized to a cation, injection and transport of holes from the mixed region to an electroluminescent medium are facilitated.
- Preferable oxidative dopants include various Lewis acids and acceptor compounds.
- Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. Further, a white-emitting electroluminescent device having two or more electroluminescent layers may be manufactured by employing a reductive dopant layer as a charge generating layer.
- an organic electroluminescent compound can exhibit high luminous efficiency and can have excellent material life, and can be used to manufacture OLED devices having very superior operating life.
- Compound 1-1 (28g, 100.68mmol) was mixed with triethylphosphite 300mL and stirred at 150°C for 6 hours. The mixture was cooled to room temperature, distilled under reduced pressure, extracted with EA, and then washed with distilled water. Subsequently, drying with anhydrous MgSO 4 , distillation under reduced pressure and then column separation were conducted, yielding Compound 1-2 (11g, 44.69mmol, 44.38%).
- Compound 1-2 (30g, 101.29mmol), iodobenzene (41.3g, 202.59mmol), CuI (9.6g, 50.64mmol), Cs 2 CO 3 (82.5g, 253.2mmol), and toluene 600mL were mixed and heated at 50°C, and ethylenediamine (6.8mL, 101.29mmol) was added. The mixture was stirred under reflux. 14 hours later, the mixture was cooled to room temperature and distilled water was added. The mixture was extracted with EA, dried with anhydrous MgSO 4 , distilled under reduced pressure and column separated, yielding Compound 1-3 (32g, 85.96mmol, 84.86%).
- Dibenzo[b,d]thiophen-4-ylboronic acid (10g, 43.84mmol), bromonitrobenzene (8.85g, 43.84mmol), 2M Na 2 CO 3 aqueous solution 70mL, toluene 200mL, and ethanol 70mL were mixed and stirred under reflux. 5 hours later, the mixture was cooled to room temperature, extracted with EA, washed with distilled water, dried with anhydrous MgSO 4 , and distilled under reduced pressure. Subsequently, column separation was carried out, yielding Compound 2-1 (10g, 32.74mmol, 74.68%).
- Compound 2-1 (10g, 32.74mmol) was mixed with triethylphosphite 100mL, and stirred at 150°C for 7 hours. The mixture was cooled to room temperature and distilled under reduced pressure. Subsequently, recrystallization was conducted using EA, yielding Compound 2-2 (7g, 25.60mmol, 78.19%).
- Compound 2-3 (8.2g, 19.1mmol, 75%) was prepared by the same method as in the preparation of Compound 1-7 .
- Compound 2-4 (4.7g, 12.0mmol, 62%) was prepared by the same method as in the preparation of Compound 1-8 .
- Compound 10 (5.3g, 9.2mmol, 67%) was prepared by the same method as in the preparation of Compound 1 .
- Compound 3-8 (5.8g, 11.0mmol, 59%) was prepared by the same method as in the preparation of Compound 1-7 .
- Compound 3-9 (3.6g, 7.3mmol, 67%) was prepared by the same method as in the preparation of Compound 1-8 .
- Compound 19 (5.0g, 9.2mmol, 69%) was prepared by the same method as in the preparation of Compound 1 .
- Compound 4-3 (8.4g, 20.4mmol, 75%) was prepared by the same method as in the preparation of Compound 1-7 .
- Compound 4-4 (4.3g, 11.4mmol, 56%) was prepared by the same method as in the preparation of Compound 1-8 .
- Compound 20 (2.8g, 5.0mmol, 42%) was prepared by the same method as in the preparation of Compound 1 .
- An OLED device was manufactured using the compound for organic electronic materials 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 deposition apparatus, and 2-TNATA [4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine] was placed in a cell of the vacuum deposition apparatus, which was then evacuated up to 10 -6 torr of vacuum in the chamber.
- Compound 10 as a host was placed in a cell, and 11-(4,6-diphenyl-1,3,5-triazin-2-yl)-12-phenyl-11,12-dihydroindolo[2,3-a]carbazole was placed in another cell, within a vacuum vapor deposition apparatus.
- the two materials were evaporated at the same rate and used as a host.
- a dopant, D-5, was added so that the host was 15 wt% doped, and thereby the electroluminescent layer was vapor-deposited to a thickness of 30 nm on the hole transport layer.
- Alq tris(8-hydroxyquinoline)-aluminum(III)
- Liq lithium quinolate
- Al cathode was vapor-deposited to a thickness of 150 nm using another vacuum vapor deposition apparatus to manufacture an OLED.
- Each compound used in the OLED device was purified by vacuum sublimation at 10 -6 torr before use.
- An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 11 was used as the host material, and D-34 was used as a dopant in the electroluminescent layer.
- An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 21 was used as the host material, and D-34 was used as a dopant in the electroluminescent layer.
- An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 28 was used alone as the host material in the electroluminescent layer.
- An OLED device was manufactured by the same method as in Example 1, with the exception that an electroluminescent layer was vapor-deposited using CBP (4,4'-bis(carbazol-9-yl)biphenyl) used as a host and Compound D-4 as a dopant, and a hole blocking layer was vapor-deposited to a thickness of 10 nm using aluminum(III)bis(2-methyl-8-quinolinato)4-phenylphenolate between the electroluminescent layer and the electron transport layer.
- CBP 4,4'-bis(carbazol-9-yl)biphenyl
- the devices using the organic electroluminescent compounds of the present invention as a host material can exhibit superior electroluminescent properties and can reduce operating voltage to thus increase power efficiency, thereby improving power consumption.
- an organic electroluminescent compound can exhibit high luminous efficiency and can have excellent material life, and can be used to manufacture OLED devices having very superior operating life.
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Abstract
L'invention concerne des composés électroluminescents organiques qui comporte un triphénylène conjugué à un système hétérocyclique à cinq cycles fusionnés, tel qu'illustré dans la formule 1. L'invention concerne également un dispositif électroluminescent organique comportant ces composés. Les composés électroluminescents organiques, divulgués par les présentes, permettent d'obtenir un bon rendement lumineux et une excellente durée de vie de matériau. Ils peuvent être utilisés pour fabriquer des dispositifs à DELO qui sont très supérieurs en termes de durée de vie de fonctionnement et qui consomment moins d'énergie en raison d'un rendement énergétique amélioré.
Priority Applications (2)
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| CN201180055620XA CN103228661A (zh) | 2010-09-20 | 2011-09-16 | 新有机电致发光化合物和使用该化合物的有机电致发光器件 |
| JP2013529070A JP2013544759A (ja) | 2010-09-20 | 2011-09-16 | 新規有機電界発光化合物およびこれを使用する有機電界発光素子 |
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| KR20100092223 | 2010-09-20 | ||
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| KR10-2011-0092141 | 2011-09-09 | ||
| KR1020110092141A KR20120030941A (ko) | 2010-09-20 | 2011-09-09 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 |
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