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Definitions

• the present invention relates to organic electroluminescence compounds and organic electroluminescence device comprising the same.
• An electroluminescence 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 for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
• the most important factor determining luminous efficiency in an organic EL device is the light-emitting material.
• fluorescent materials have been widely used as a 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 materials, respectively.
• CBP 4,4’-N,N’-dicarbazol-biphenyl
• BCP bathocuproine
• BAlq aluminum(III)bis(2-methyl-8-quinolinate)(4-phenylphenolate)
• 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
• an organic EL device using these materials is problematic in quantum efficiency and operational lifespan. It is because, when an organic EL device is driven under high current, thermal stress occurs between an anode and the hole injection layer. Thermal stress significantly reduces the operational lifespan of the device. Further, 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/A) may decrease.
• Korean Patent No. 10-1161289 and Korean Patent Appln. Laying-Open No. 10-2012-0048125 disclose compounds in which anthracene, pyrene, etc., are bonded to an indoline backbone, as fluorescent materials for an organic EL device.
• the objective of the present invention is to provide an organic electroluminescent compound which has excellent current efficiency and luminous efficiency.
• ring A represents a ring selected from the following formulas 2 to 4;
• X represents a single bond or -CR 8 R 9 -;
• L 1 represents a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 3- to 30- membered heteroarylene;
• L 2 and L 3 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 3- to 30- membered heteroarylene;
• Y represents -NR 10 , -O-, -S-, or -CR 11 R 12 -;
• R 1 to R 12 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, a substituted or unsubstituted 3- to 30- membered heteroaryl, -NR 13 R 14
• R 13 to R 22 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 3- to 30- membered heteroaryl; or are linked to an
• a and b each independently represent 1 or 2
• c to e each independently represent an integer of 1 to 4
• f and g each independently represent an integer of 1 to 6
• a to g are integers of 2 or more, each of R 1 to R 7 may be the same or different;
• organic electroluminescent compound according to the present invention By using the organic electroluminescent compound according to the present invention, it is possible to manufacture an organic electroluminescent device which has excellent current efficiency and luminous efficiency.
• the present invention relates to an organic electroluminescent compound of formula 1, an organic electroluminescent material comprising the compound, and an organic electroluminescent device comprising the material.
• the electroluminescent compound represented by the above formula 1 will be described in detail.
• ring A is represented by formula 2.
• ring A is represented by formula 3.
• ring A is represented by formula 4.
• 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 L 1 to L 3 , and R 1 to R 22 in the above formula 1 each independently are 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,
• L 1 represents a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 3- to 30- membered heteroarylene, preferably represents an unsubstituted (C6-C21)arylene, or an unsubstituted 5- to 21- membered heteroarylene, and more preferably represents an unsubstituted (C6-C10)arylene, or an unsubstituted 5- to 7- membered heteroarylene.
• L 2 and L 3 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 3- to 30- membered heteroarylene, preferably each independently represent a single bond, an unsubstituted (C6-C21)arylene, or an unsubstituted 5- to 21- membered heteroarylene, and more preferably each independently represent a single bond, an unsubstituted (C6-C10)arylene, or an unsubstituted 5- to 7- membered heteroarylene.
• R 1 to R 12 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, a substituted or unsubstituted 3- to 30- membered heteroaryl, -NR 13 R 14
• ring A represents a ring selected from formulas 2 to 4;
• X represents a single bond or -CR 8 R 9 -;
• L 1 represents an unsubstituted (C6-C21)arylene, or an unsubstituted 5- to 21- membered heteroarylene;
• L 2 and L 3 each independently represent a single bond, an unsubstituted (C6-C21)arylene, or an unsubstituted 5- to 21- membered heteroarylene;
• Y represents -NR 10 -, -O-, -S- or -CR 11 R 12 -; and
• R 1 to R 12 each independently represent hydrogen, an unsubstituted (C1-C6)alkyl, an unsubstituted (C6-C21)aryl, or a substituted or unsubstituted 5- to 21- membered heteroaryl; or are linked to an adjacent substituent(s) to form a monocyclic, 5- to 21-
• ring A represents a ring selected from formulas 2 to 4;
• X represents a single bond or -CR 8 R 9 -;
• L 1 represents an unsubstituted (C6-C10)arylene, or an unsubstituted 5- to 7- membered heteroarylene;
• L 2 and L 3 each independently represent a single bond, an unsubstituted (C6-C10)arylene, or an unsubstituted 5- to 7- membered heteroarylene;
• Y represents -NR 10 -, -O-, -S- or -CR 11 R 12 -; and
• R 1 to R 12 each independently represent hydrogen; an unsubstituted (C1-C4)alkyl; an unsubstituted (C6-C12)aryl; or a 5- to 7- membered heteroaryl unsubstituted or substituted with a (C6-C10)aryl; or are linked to an adjacent substituent(s) to form
• the specific compounds of the present invention include the following compounds, but are not limited thereto:
• organic electroluminescent compounds of the present invention can be prepared by a synthetic method known to a person skilled in the art. For example, they can be prepared according to the following reaction schemes 1 to 3.
• 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 above material can be comprised of the organic electroluminescent compound according to the present invention alone, or can further include conventional materials generally used in organic electroluminescent materials.
• Said organic electroluminescent device comprises a first electrode; a second electrode; and at least one organic layer between said first and second electrodes.
• Said organic layer may comprise at least one organic electroluminescent compound of formula 1 according to the present invention.
• the organic layer comprises a light-emitting layer, and may further comprise at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer.
• Said hole transport layer may be comprised of two or more hole transport layers, and when there are two or more hole transport layers, the efficiency and the lifespan of the organic electroluminescent device may be improved.
• the organic electroluminescent compound represented by formula 1 can be comprised in at least one of the light-emitting layer and the hole transport layer. Where used in the hole transport layer, the organic electroluminescent compound represented by formula 1 can be comprised as a hole transport material. Where used in the light-emitting layer, the organic electroluminescent compound represented by formula 1 can be comprised as a host material.
• the organic electroluminescent device comprising the organic electroluminescent compound according to the present invention may comprise at least one compound other than the organic electroluminescent compound according to the present invention as a host material, and can further comprise at least one dopant.
• the organic electroluminescent compound according to the present invention is comprised as a host material (first host material)
• the other compound may be comprised as a second host material.
• the ratio of the first host material to the second host material is in the range of 1:99 to 99:1.
• Another host material other than the organic electroluminescent compound according to the present invention can be from any of the known phosphorescent hosts. Specifically, the phosphorescent host selected from the group consisting of the compounds of formulae 5 to 7 below is preferable in view of luminous efficiency.
• R 31 to R 34 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 3- to 30-membered heteroaryl, or R 35 R 36 R 37 Si-; R 35 to R 37 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; Y 1 and Y 2 each independently represent -
• preferable examples of said host material are as follows:
• the dopant is preferably at least one phosphorescent dopant.
• the phosphorescent dopant material applied to the electroluminescent device according to the present invention is not limited, but may be preferably selected from metallated complex compounds of iridium, osmium, copper and platinum, more preferably selected from ortho-metallated complex compounds of iridium, osmium, copper and platinum, and even more preferably ortho-metallated iridium complex compounds.
• the phosphorescent dopants may be preferably selected from compounds represented by the following formulae 8 to 10.
• L is selected from the following structures:
• R 100 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl;
• 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 a halogen(s); a substituted or unsubstituted (C3-C30)cycloalkyl; a cyano; or a substituted or unsubstituted (C1-C30)alkoxy; adjacent substituents of R 120 to R 123 may be linked to each other to form a fused ring, e.g. quinoline;
• 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 groups, adjacent substituents may be linked to each other to form a fused ring, e.g. fluorene;
• R 201 to R 211 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen(s), or a substituted or unsubstituted (C3-C30)cycloalkyl;
• o and p each independently represent an integer of 1 to 3; where o or p 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:
• composition for an organic electroluminescent device comprises the compound according to the present invention as a host material or a hole transport layer.
• the organic electroluminescent device comprises a first electrode; a second electrode; and at least one organic layer between said first and second electrodes.
• Said organic layer comprises a light-emitting layer, and the light-emitting layer may comprise the composition used for the organic electroluminescent device according to the present invention.
• the organic electroluminescent device according to the present invention may further comprise, in addition to the organic electroluminescent compound represented by 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 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 d-transition elements of the Periodic Table, or at least one complex compound comprising said metal.
• the organic layer may further comprise a light-emitting layer and a charge generating layer.
• said organic layer may form an organic electroluminescent device emitting 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 organic electroluminescent compound according to the present invention.
• a surface layer is preferably 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.
• said chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.; said metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and said metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
• a mixed region of an electron transport compound and an reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant is preferably 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; and 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.
• a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
• the solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
• reaction mixture was then extracted with ethylacetate/H 2 O, moisture was removed with MgSO 4 , and the remaining substance was distilled under reduced pressure.
• the product was separated with column chromatography to obtain a white solid compound 1-4 (5 g, 30 %).
• An OLED device was produced using the light emitting 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.
• compound C-83 according to the present invention 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. Thereafter, 9-(4,6-diphenylpyrimidin-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole 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.
• 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 8090 cd/m 2 and a current density of 18.5 mA/cm 2 .
• An OLED device was produced in the same manner as in Device Example 1, except for forming a hole transport layer having a thickness of 20 nm using compound C-5 , introducing 9-phenyl-9'-(4-phenylquinazolin-2-yl)-9H,9'H-3,3'-bicarbazole into one cell of the vacuum vapor depositing apparatus, introducing compound D-37 into another cell as a dopant, and evaporating the two materials at different rates and depositing them 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 2470 cd/m 2 and a current density of 20.9 mA/cm 2 .
• Comparative Example 1 Luminous characteristic of an OLED device
• An OLED device was produced in the same manner as in Device Example 1, except for evaporating N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl as a hole transport material to form a hole transport layer having a thickness of 20 nm; using 4,4'-N,N'-dicarbazole-biphenyl (CBP) as a host material, compound D-15 as a dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer; and depositing aluminum(III)bis(2-methyl-8-quinolinato)4-phenylphenolate to form a hole blocking layer having a thickness of 10 nm.
• CBP 4,4'-N,N'-dicarbazole-biphenyl
• the produced OLED device showed a green emission having a luminance of 2850 cd/m 2 and a current density of 8.40 mA/cm 2 .
• Comparative Example 2 Luminous characteristic of an OLED device
• An OLED device was produced in the same manner as in Device Example 1, except for evaporating N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl as a hole transport material to form a hole transport layer having a thickness of 20 nm; using 4,4'-N,N'-dicarbazole-biphenyl (CBP) as a host material, compound D-50 as a dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer; and depositing aluminum(III)bis(2-methyl-8-quinolinato)4-phenylphenolate to form a hole blocking layer having a thickness of 10 nm.
• CBP 4,4'-N,N'-dicarbazole-biphenyl
• the produced OLED device showed a red emission having a luminance of 1080 cd/m 2 and a current density of 15.4 mA/cm 2 .
• organic electroluminescent compound according to the present invention By using the organic electroluminescent compound according to the present invention, it is possible to manufacture an organic electroluminescent device which has excellent current efficiency and luminous efficiency.

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