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Definitions

• the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device containing the same.
• An electroluminescent (EL) device is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
• An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules, and aluminum complexes as materials to form a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
• the most important factor determining luminous efficiency in the organic EL device is light-emitting materials.
• fluorescent materials have been widely used as the light-emitting material.
• phosphorescent materials theoretically enhance luminous efficiency by four (4) times compared to fluorescent materials, development of phosphorescent light-emitting materials are widely being researched.
• Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C3’)iridium(acetylacetonate) ((acac)Ir(btp) 2 ), tris(2-phenylpyridine)iridium (Ir(ppy) 3 ) and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red-, green- and blue-emitting materials, respectively.
• the light-emitting material can be used as a combination of a host material and a dopant to improve color purity, luminous efficiency, and stability.
• the host materials greatly influence the efficiency and performance of the EL device when using a host material/dopant system as the light emitting material, and thus their selection is important.
• 4,4’-N,N’-dicarbazol-biphenyl (CBP) is the most widely known host material for phosphorescent materials.
• phosphorescent host materials provide good light-emitting characteristics, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, their degradation may occur during a high-temperature deposition process in a vacuum. (2) The power efficiency of the organic EL device is given by [( ⁇ /voltage) ⁇ current efficiency], and the power efficiency is inversely proportional to the voltage. Although the organic EL device comprising phosphorescent host materials provides higher current efficiency (cd/A) than one comprising fluorescent materials, a significantly high driving voltage is necessary. Thus, there is no merit in terms of power efficiency (lm/W). (3) Furthermore, the operational lifespan of the organic EL device is short, and luminous efficiency is still required in order to be improved.
• CuPc copper phthalocyanine
• NPB 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl
• TPD N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine
• MTDATA 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine
• MTDATA 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine
• the organic EL device using these materials is problematic in quantum efficiency and operational lifespan. It is because, when the organic EL device is driven under high current, thermal stress occurs between an anode and a hole injection layer. Thermal stress significantly reduces the operational lifespan of the device. Furthermore, since the organic material used in the hole injection layer has very high hole mobility, the hole-electron charge balance may be broken and quantum yield (cd/
• Korean Patent Application Laying-Open No. 20110129766 discloses compounds for an organic EL device, in which aryl or heteroaryl moiety is bonded to a carbon atom of a polycyclic compound having carbazole moiety fused with heteroaryl moiety such as benzofuran and benzothiophene.
• heteroaryl moiety such as benzofuran and benzothiophene.
• the above reference fails to specifically disclose compounds in which nitrogen-containing heteroaryl moiety, nitrogen-connected heteroaryl moiety (containing or not-containing nitrogen) or nitrogen-connected aryl moiety is bonded to a nitrogen atom of a carbazole moiety of a polycyclic backbone.
• the objective of the present invention is to provide an organic electroluminescent compound, which has higher luminous efficiency and a longer lifespan than the conventional materials, and an organic electroluminescent device, which has high efficiency and a long lifespan, using said compounds.
• X represents -O-, -S-, -CR 1 R 2 - or -NR 3 -;
• L 1 represents a substituted or unsubstituted 5- to 30-membered heteroarylene, or a substituted or unsubstituted (C6-C30)arylene;
• Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted 5- to 30-membered heteroaryl, or a substituted or unsubstituted 5- to 30-membered heteroarylene;
• Ar 1 and Ar 2 , Ar 3 and L 1 , or Ar 3 and Ar 4 may be linked together with a nitrogen atom bonded thereto to form a nitrogen-containing 5- or 30-membered heteroaryl or a nitrogen-containing 5- or 30-membered heteroarylene;
• R 1 to R 3 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-musined heteroaryl, or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring;
• R 4 and R 5 each independently represent hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17
• R 11 to R 20 each independently represent hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl, or are linked to an
• n and n each independently represent an integer of 1 to 4; where m or n is an integer of 2 or more, each of R 4 or each of R 5 may be the same or different; and
• the compounds according to the present invention show high luminous efficiency and a long lifespan. Using the compound according to the present invention, an electroluminescent device exhibits excellent luminous characteristics and current efficiency.
• the present invention provides the organic electroluminescent compound of formula 1 above, an organic electroluminescent material comprising the same, and an organic electroluminescent device comprising the material.
• the compound of formula 1 of the present invention is as follows.
• X represents -O-, -S-, -CR 1 R 2 - or -NR 3 -;
• L 1 represents a substituted or unsubstituted (C6-C30)arylene;
• Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6-C15)aryl, a substituted or unsubstituted (C6-C15)arylene, a substituted or unsubstituted 5- to 15-membered heteroaryl, or a substituted or unsubstituted 5- to 15-membered heteroarylene;
• Ar 1 and Ar 2 , Ar 3 and L 1 , or Ar 3 and Ar 4 may be linked together with a nitrogen atom bonded thereto to form a nitrogen-containing 5- or 15-membered heteroaryl or a nitrogen-containing 5- or 15-membered heteroarylene;
• R 1 to R 3 each independently represent a substituted or unsubstituted (C1-C15)alkyl,
• X represents -O-, -S-, -CR 1 R 2 - or -NR 3 -;
• L 1 represents an unsubstituted (C6-C15)arylene;
• Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6-C15)aryl, a substituted or unsubstituted (C6-C15)arylene, a substituted or unsubstituted 5- to 15-membered heteroaryl, or a substituted or unsubstituted 5- to 15-membered heteroarylene;
• Ar 1 and Ar 2 , Ar 3 and L 1 , or Ar 3 and Ar 4 may be linked together with a nitrogen atom bonded thereto to form a nitrogen-containing 5- or 15-membered heteroaryl or a nitrogen-containing 5- or 15-membered heteroarylene;
• R 1 and R 2 each independently represent a substituted or unsubstituted (C1-C10)alkyl, or a substituted
• (C1-C30)alkyl indicates a linear or branched alkyl having 1 to 30, preferably 1 to 10 carbon atoms and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
• “(C2-C30) alkenyl” indicates a linear or branched alkenyl having 2 to 30, preferably 2 to 20, more preferably 2 to 10 carbon atoms and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
• (C2-C30)alkynyl indicates a linear or branched alkynyl having 2 to 30, preferably 2 to 20, more preferably 2 to 10 carbon atoms and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
• “(C3-C30)cycloalkyl” indicates a mono- or polycyclic hydrocarbon having 3 to 30, preferably 3 to 20, more preferably 3 to 7 carbon atoms and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
• (C6-C30)aryl(ene) indicates a monocyclic or fused ring derived from an aromatic hydrocarbon and having 6 to 30, preferably 6 to 15 ring backbone carbon atoms, and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.
• substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent.
• the substituents of the substituted alkyl, the substituted alkenyl, the substituted alkynyl, the substituted alkoxy, the substituted cycloalkyl, the substituted cycloalkenyl, the substituted heterocycloalkyl, the substituted aryl(ene), and the substituted heteroaryl(ene) in formula 1 above, each independently, are preferably at least one selected from the group consisting of deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a (C1-C30)alkyl, a halo(C1-C30)alkyl, a (C2-C30)alkenyl, a (C2-C30)alkyn
• Organic electroluminescent compounds of the present invention include the following, but are not limited thereto:
• the compounds of the present invention can be prepared by a synthetic method known to one skilled in the art. For example, they can be prepared according to the following reaction scheme 1.
• the present invention provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the material.
• the organic electroluminescent material may consist of the organic electroluminescent compound of formula 1. Otherwise, the organic electroluminescent material may further comprise a conventional compound(s), in addition to the organic electroluminescent compound of formula 1.
• the organic electroluminescent device may comprise a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes.
• the organic layer may comprise at least one compound of formula 1.
• the organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and a electron blocking layer.
• the compound of formula 1 may be comprised in at least one of the light-emitting layer and the hole transport layer.
• the compound of formula 1 When used in the hole transport layer, the compound of formula 1 may be comprised as a hole transport material.
• the compound of formula 1 When used in the light-emitting layer, the compound of formula 1 may be comprised as a host material; preferably, the light-emitting layer may further comprise at least one dopant, and, if needed, a compound other than the compound of formula 1 may be comprised additionally as a second host material.
• the second host material may be from any of the known phosphorescent host materials. Specifically, the phosphorescent host material selected from the compounds of formulae 2 to 4 below is preferable in view of luminous efficiency.
• Cz represents the following structure
• R 21 to R 24 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted of unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, or R 25 R 26 R 27 Si-;
• R 25 to R 27 each independently represent a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl;
• L 4 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 5- to 30-membered heteroarylene;
• M represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl;
• the second host material includes the following:
• the dopant for the organic electroluminescent device of the present invention is preferably at least one phosphorescent dopant.
• the phosphorescent dopant for the electroluminescent device of the present invention is not limited, but may be preferably selected from metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
• the phosphorescent dopants may be preferably selected from compounds represented by the following formulae 5 to 7.
• L is selected from the following:
• R 100 represents hydrogen, or a substituted or unsubstituted (C1-C30)alkyl
• R 101 to R 109 , and R 111 to R 123 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with halogen(s), a cyano, or a substituted or unsubstituted (C1-C30)alkoxy
• R 120 to R 123 may be linked with an adjacent substituent(s) to form a fused ring, e.g.
• R 124 to R 127 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl; where R 124 to R 127 are aryl, they may be linked with an adjacent substituent(s) to form a fused ring, e.g.
• R 201 to R 211 each independently represent hydrogen, deuterium, a halogen, or a (C1-C30)alkyl unsubstituted or substituted with halogen(s);
• f and g each independently represent an integer of 1 to 3, where f or g is an integer of 2 or more, each of R 100 may be the same or different, and n is an integer of 1 to 3.
• the phosphorescent dopant materials include the following:
• the present invention provides a material for preparing an organic electroluminescent device.
• the material comprises the organic electroluminescent compound of the present invention as a host material or a hole transport material.
• the material for preparing an organic electroluminescent device may further comprise a second host material, in which the ratio of the first host material to the second host material may be in the range of 1:99 to 99:1.
• the organic electroluminescent device of the present invention comprises a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes.
• the organic layer comprises the material for preparing the organic electroluminescent device of the present invention.
• the organic layer of the organic electroluminescent device of the present invention may further comprise, in addition to the compound of formula 1, at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
• the organic layer may further comprise, in addition to the compound of formula 1, at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising said metal.
• the organic layer may comprise a light-emitting layer and a charge generating layer.
• the organic electroluminescent device of the present invention may emit white light by further comprising at least one light-emitting layer, which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound known in the field, besides the compound of the present invention. Also, if needed, a yellow or orange light-emitting layer can be comprised in the device.
• a surface layer may be placed on an inner surface(s) of one or both electrode(s), selected from a chalcogenide layer, a metal halide layer and a metal oxide layer.
• a chalcogenide (includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer
• a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
• Such a surface layer provides operation stability for the organic electroluminescent device.
• the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
• the metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
• 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 may be placed on at least one surface of a pair of electrodes.
• the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
• the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
• the oxidative dopant includes various Lewis acids and acceptor compounds
• the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
• a reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting white light.
• dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as spin coating, dip coating, and flow coating methods can be used.
• Compound 2-4 was prepared in the same manner as compound 2-3 of Example 1.
• a mixture of compound 2-3 (5.9g, 14mmol), 3-bromo-N,N-diphenylaniline (5g, 15 mmol), CuI (1.3g, 6.9mmol), K 3 PO 4 (8.9g, 42mmol), ethylene diamine (1.9ml, 28mmol), and toluene (70mL) was stirred in a 250mL sized RBF at 120°C overnight. After treating the reaction mixture with EA/H 2 O, it was dried with MgSO 4 and distilled under reduced pressure. The crude product was purified with a column chromatography using MC/hexane(Hx) to obtain compound C-6 (white solids, 6.9 g, 74%).
• An OLED device was produced using the material according to the present invention.
• a transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and then was stored in isopropanol. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
• N 1 ,N 1' -([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -(naphthalen-1-yl)-N 4 ,N 4 -diphenylbenzen-1,4-diamine) was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
• organic electroluminescent compound C-2 was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
• 5-(4-([1,1’:4’,1”-terphenyl]-3-yl)pyrimidin-2-yl)-5H-benzo[4,5]thieno[3,2-c]carbazole was introduced into one cell of the vacuum vapor depositing apparatus, as a host material, and compound D-1 was introduced into another cell as a dopant.
• the two materials were evaporated at different rates and were deposited in a doping amount of 15 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Then, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[ d ]imidazole was introduced into one cell and lithium quinolate was introduced into another cell. The two materials were evaporated at the same rate and were deposited in a doping amount of 50 wt% each to form an electron transport layer having a thickness of 30 nm on the light-emitting layer.
• an Al cathode having a thickness of 150 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer.
• An OLED device was produced. All the materials used for producing the OLED device were purified by vacuum sublimation at 10 -6 torr prior to use.
• the produced OLED device showed a green emission having a luminance of 5350 cd/m 2 and a current density of 13.1 mA/cm 2 .
• An OLED device was produced in the same manner as in Device Example 1, except that compound C-71 was used to form a hole transport layer having a thickness of 20 nm, and both 9-(4-([1,1’:3’,1”-terphenyl]-4-yl)pyrimidin-2-yl)-3-(dibenzo[b,d]thiophen-4-yl)-9H-carbazole in one cell of the vacuum vapor depositing apparatus, as a host material, and compound D-25 in another cell as a dopant were evaporated at different rates and were deposited in a doping amount of 15 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer.
• the produced OLED device showed a green emission having a luminance of 11000 cd/m 2 and a current density of 24.1 mA/cm 2 .
• An OLED device was produced in the same manner as in Device Example 1, except that compound C-6 was used to form a hole transport layer having a thickness of 20 nm, and both 9-(4-([1,1’-biphenyl]-4-yl)quinazolin-2-yl)-9’-phenyl-9H,9’H-3,3’-bicarbazole in one cell of the vacuum vapor depositing apparatus as a host material, and compound D-78 in another cell as a dopant were evaporated at different rates and were deposited in a doping amount of 3 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer.
• the produced OLED device showed a red emission having a luminance of 7000 cd/m 2 and a current density of 50.4 mA/cm 2 .
• An OLED device was produced in the same manner as in Device Example 1, except that compound C-62 was used to form a hole transport layer having a thickness of 20 nm.
• the produced OLED device showed a green emission having a luminance of 3000 cd/m 2 and a current density of 7.1 mA/cm 2 .
• Comparative Device Example 1 an OLED device using conventional materials
• An OLED device was produced in the same manner as in Device Example 1, except that N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl was used to form a hole transport layer having a thickness of 20 nm; 4,4'-N,N'-dicarbazole-biphenyl as a host material and Ir(ppy) 3 ( D-15 ) as a dopant were used to form a light-emitting layer having a thickness of 30 nm on the hole transport layer; and aluminum(III) bis(2-methyl-8-quinolinato)-4-phenylphenolate was used to form a hole blocking layer having a thickness of 10 nm.
• the produced OLED device showed a green emission having a luminance of 2750 cd/m 2 and a current density of 8.30 mA/cm 2 .
• Comparative Device Example 2 an OLED device using conventional materials
• An OLED device was produced in the same manner as in Device Example 1, except that N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl was used to form a hole transport layer having a thickness of 20 nm; both CBP as a host material and D-80 as a dopant were used to form a light-emitting layer having a thickness of 30 nm on the hole transport layer; and aluminum(III) bis(2-methyl-8-quinolinato)-4-phenylphenolate was used to form a hole blocking layer having a thickness of 10 nm.
• the produced OLED device showed a red emission having a luminance of 1700 cd/m 2 and a current density of 32.1 mA/cm 2 .
• the organic electroluminescent compounds of the present invention have superior characteristics over conventional materials, and so the devices using the organic electroluminescent compounds of the present invention exhibit superior luminous characteristics and current efficiency.

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