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Definitions

• the present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising 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 light-emitting material.
• phosphorescent materials theoretically enhance luminous efficiency by four (4) times compared to fluorescent materials, phosphorescent light-emitting materials have been widely being researched.
• Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C-3’)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.
• CBP 4,4’-N,N’-dicarbazol-biphenyl
• BCP bathocuproine
• BAlq aluminum(III) bis(2-methyl-8-quinolinate)(4-phenylphenolate)
• the organic EL device may be manufactured with a multi-layered structure in which a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc., are comprised.
• a compound for the hole transport layer is important to enhance characteristics of the device, such as efficiency for transporting holes to the light-emitting layer, luminous efficiency, and lifespan.
• 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
• Korean Patent Application Laying-open No. 10-2012-0029446, WO 2013-065589, and WO 2007-119800 disclose an amine derivative having a benzofluorene-based substituent, as a compound for an organic EL device.
• benzofluorene-based substituents of the references are benzo[ a ]fluorene- or benzo[ c ]fluorene-based substituents.
• An amine derivative having a benzo[ b ]fluorene-based substituent is not specifically disclosed in the references.
• the objective of the present disclosure is to provide an organic electroluminescent compound showing luminous efficiency such as current efficiency, and an organic electroluminescent device comprising the same.
• Ar 1 to Ar 4 each independently, represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; and Ar 1 and Ar 2 may be fused with each other to form a ring;
• Ar 5 represents a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
• L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene;
• L 2 represents a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene;
• R 1 and R 2 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -N(R 11 )(R 12 ), -Si(R 13 )(R 14 )(R 15 ), -S(R 16 ), -O(R 17 ), a cyano, a nitro, or a hydroxyl; or may be linked to an adjacent substituent(s) to form
• R 11 to R 17 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent(s) to form a (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
• n and m each independently, represent 0 or 1, provided that both n and m cannot be simultaneously 0;
• a represents an integer of 1 to 3; where a is an integer of 2 or more, each of R 1 may be the same or different;
• b represents an integer of 1 to 6; where b is an integer of 2 or more, each of R 2 may be the same or different;
• the heterocycloalkyl contains at least one hetero atom selected from O, S, and N.
• the organic electroluminescent compound of the present disclosure can provide an organic electroluminescent device showing excellence in luminous efficiency such as current efficiency.
• the present disclosure provides the organic electroluminescent compound of formula 1 above, an organic electroluminescent material comprising the organic electroluminescent compound, and an organic electroluminescent device comprising the organic electroluminescent compound.
• alkyl includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
• Alkenyl includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
• Alkynyl includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
• Cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
• aryl(ene) indicates a monocyclic or fused ring derived from an aromatic hydrocarbon, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, 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 for the substituted alkyl(ene), the substituted aryl(ene), the substituted heteroaryl(ene), the substituted cycloalkyl, the substituted heterocycloalkyl, and the substituted arylalkyl of Ar 1 to Ar 5 , L 1 , L 2 , R 1 , R 2 , and R 11 to R 17 of formula 1, each independently, are at least one selected from the group consisting of deuterium; a halogen; a (C1-C30)alkyl unsubstituted or substituted with a halogen; a (C1-C30)alkoxy; a (C6-C30)aryl; a (3- to 30-membered)heteroaryl unsubstitute
• the compound of formula 1 is represented by any one of the following formulae 2 to 4, and preferably the following formula 2 or 3:
• Ar 1 to Ar 5 , L 1 , L 2 , R 1 , R 2 , a and b are as defined in formula 1 above.
• Ar 1 to Ar 4 each independently, represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, and Ar 1 and Ar 2 may be fused with each other to form a ring.
• Ar 1 to Ar 4 each independently, represent a substituted or unsubstituted (C6-C21)aryl, or a substituted or unsubstituted (5- to 21-membered)heteroaryl, and Ar 1 and Ar 2 may be fused with each other to form a ring; and more preferably, represent a substituted or unsubstituted (C6-C21)aryl, the substituent of the (C6-C21)aryl may be at least one selected from the group consisting of a (C1-C30)alkyl, a (C6-C21)aryl unsubstituted or substituted with a (C1-C10)alkyl, and a (5- to 21-membered)heteroaryl unsubstituted or substituted with a (C6-C12)aryl, and Ar 1 and Ar 2 may be fused with each other to form a ring.
• Ar 1 to Ar 4 each independently, may represent phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, or benzofluorenyl, and Ar 1 and Ar 2 may be fused with each other to form a ring.
• the substituent of Ar 1 to Ar 4 may be at least one selected from the group consisting of a (C1-C4)alkyl, phenyl, naphthyl, fluorenyl, 9,9-dimethyl-9H-fluorenyl, pyridyl, pyrimidyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, 9-phenylcarbazolyl, dibenzothiophenyl, and dibenzofuranyl.
• a (C1-C4)alkyl phenyl, naphthyl, fluorenyl, 9,9-dimethyl-9H-fluorenyl, pyridyl, pyrimidyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, 9-phenylcarbazolyl, dibenzothiophenyl, and dibenzofuranyl.
• the ring formed by Ar 1 and Ar 2 may be represented by the following formula 5:
• R 3 and R 4 each independently, represent hydrogen, a (C1-C30)alkyl, a (C6-C30)aryl, or a (3- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl; and * represents a site for connecting to L 1 .
• one of R 3 and R 4 represents hydrogen, and the other may be selected from the group consisting of a (C1-C4)alkyl; phenyl; biphenyl; naphthyl; carbazolyl unsubstituted or substituted with phenyl, biphenyl, or naphthyl; dibenzothiophenyl unsubstituted or substituted with phenyl, biphenyl, or naphthyl; and dibenzofuranyl unsubstituted or substituted with phenyl, biphenyl, or naphthyl.
• a (C1-C4)alkyl phenyl; biphenyl; naphthyl
• carbazolyl unsubstituted or substituted with phenyl, biphenyl, or naphthyl dibenzothiophenyl unsubstituted or substituted with phenyl, biphenyl, or naphthyl
• dibenzofuranyl unsub
• Ar 5 represents a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl.
• Ar 5 represents a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C21)aryl, or a substituted or unsubstituted (5- to 21-membered)heteroaryl.
• Ar 5 represents an unsubstituted (C1-C10)alkyl; a (C6-C18)aryl, unsubstituted or substituted with a (C1-C10)alkyl, a (C6-C21)aryl, a (6- to 21-membered)heteroaryl unsubstituted or substituted with a (C6-C13)aryl, or a di(C6-C18)arylamino; or a (6- to 21-membered)heteroaryl unsubstituted or substituted with a (C1-C10)alkyl or a (C6-C18)aryl and containing a hetero atom(s) selected from N, O, and S.
• Ar 5 represents a (C1-C4)alkyl; phenyl, biphenyl, naphthyl, terphenyl, phenanthrenyl, anthracenyl, or fluorenyl, unsubstituted or substituted with a (C1-C4)alkyl, phenyl, carbazolyl, diphenylpyrimidyl, diphenyltriazinyl, phenylbenzimidazolyl, diphenylamino, (phenyl)(biphenyl)amino, di(biphenyl)amino, or (phenyl)(naphthyl)amino; or carbazolyl, benzocarbazolyl, dibenzothiophenyl, benzonaphthothiophenyl, dibenzofuranyl, or benzonaphthofuranyl, unsubstituted or substituted with phenyl.
• L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene.
• L 1 represents a single bond, a substituted or unsubstituted (C6-C21)arylene, or a substituted or unsubstituted (5- to 21-membered)heteroarylene.
• L 1 represents a single bond; a (C6-C18)arylene unsubstituted or substituted with a (C1-C10)alkyl; or a (5- to 18-membered)heteroarylene unsubstituted or substituted with a (C1-C10)alkyl and containing nitrogen as a hetero atom.
• L 1 represents a single bond, phenyl, or pyrimidyl.
• L 2 represents a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene.
• L 2 represents a substituted or unsubstituted (C1-C20)alkylene, a substituted or unsubstituted (C6-C21)arylene, or a substituted or unsubstituted (5- to 21-membered)heteroarylene.
• L 2 represents an unsubstituted (C1-C10)alkylene; a (C6-C18)arylene unsubstituted or substituted with a (C1-C10)alkyl; or a (6- to 21-membered)heteroarylene unsubstituted or substituted with a (C1-C10)alkyl and containing oxygen as a hetero atom.
• L 2 represents a (C1-C4)alkyl, phenyl, biphenyl, naphthyl, fluorenyl, 9,9-dimethyl-9H-fluorenyl, or dibenzofuranyl.
• R 1 and R 2 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -N(R 11 )(R 12 ), -Si(R 13 )(R 14 )(R 15 ), -S(R 16 ), -O(R 17 ), a cyano, a nitro, or a hydroxyl, or may be linked to an adjacent substituent(s) to form
• R 11 to R 17 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent(s) to form a (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur.
• R 1 and R 2 each independently, represent hydrogen, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C21)aryl, a substituted or unsubstituted (5- to 21-membered)heteroaryl, or -N(R 11 )(R 12 ).
• R 11 and R 12 each independently, represent a substituted or unsubstituted (C6-C21)aryl.
• R 1 and R 2 each independently, represent hydrogen; an unsubstituted (C6-C18)aryl; an unsubstituted (6- to 18-membered)heteroaryl containing nitrogen as a hetero atom; or -N(R 11 )(R 12 ). More preferably, R 11 and R 12 , each independently, represent an unsubstituted (C6-C18)aryl.
• R 1 and R 2 each independently, represent hydrogen, phenyl, pyridyl, pyrimidyl, carbazolyl, diphenylamino, (phenyl)(biphenyl)amino, di(biphenyl)amino, or (phenyl)(naphthyl)amino.
• n and m each independently, represent 0 or 1, provided that both n and m cannot be simultaneously 0.
• a represents an integer of 1 to 3; where a is an integer of 2 or more, each of R 1 may be the same or different. Preferably, a represents 1.
• b represents an integer of 1 to 6; where b is an integer of 2 or more, each of R 2 may be the same or different. Preferably, b represents 1.
• Ar 1 to Ar 4 each independently, represent a substituted or unsubstituted (C6-C21)aryl, or a substituted or unsubstituted (5- to 21-membered)heteroaryl; and Ar 1 and Ar 2 may be fused with each other to form a ring;
• Ar 5 represents a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C21)aryl, or a substituted or unsubstituted (5- to 21-membered)heteroaryl;
• L 1 represents a single bond, a substituted or unsubstituted (C6-C21)arylene, or a substituted or unsubstituted (5- to 21-membered)heteroarylene;
• L 2 represents a substituted or unsubstituted (C1-C20)alkylene, a substituted or unsub
• Ar 1 to Ar 4 each independently, represent a substituted or unsubstituted (C6-C21)aryl
• the substituent of the (C6-C21)aryl may be at least one selected from the group consisting of a (C1-C30)alkyl, a (C6-C21)aryl unsubstituted or substituted with a (C1-C10)alkyl, and a (5- to 21-membered)heteroaryl unsubstituted or substituted with a (C6-C12)aryl
• Ar 1 and Ar 2 may be fused with each other to form a ring
• Ar 5 represents an unsubstituted (C1-C10)alkyl, a (C6-C18)aryl, unsubstituted or substituted with a (C1-C10)alkyl, a (C6-C21)aryl, a (6- to 21-membered)
• organic electroluminescent compound of formula 1 includes the following, but is not limited thereto:
• the organic electroluminescent compound of the present disclosure can be prepared by a synthetic method known to one skilled in the art. For example, it can be prepared according to the following reaction scheme 1 or 2.
• the present disclosure provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the material.
• the material may consist of the organic electroluminescent compound of the present disclosure. Otherwise, the material may further comprise a conventional compound(s) which has been comprised for an organic electroluminescent material, in addition to the compound of the present disclosure.
• the organic electroluminescent material may be a host material or a hole transport material.
• the organic electroluminescent device of the present disclosure 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, an electron buffer layer, and an electron blocking layer.
• the organic electroluminescent compound of the present disclosure may be comprised in at least one of the light-emitting layer and the hole transport layer.
• the organic electroluminescent compound of the present disclosure may be comprised as a hole transport material.
• the organic electroluminescent compound of the present disclosure may be comprised as a host material.
• the light-emitting layer may comprise a light-emitting material known in the art, or the organic electroluminescent compound of the present disclosure other than the one used as a hole transport material.
• the light-emitting material known in the art may be a host material known in the art, and may further comprise at least one dopant.
• the host material known in the art may be a fluorescent or phosphorescent host material known in the art.
• the organic electroluminescent compound of the present disclosure is comprised as a host material (a first host material) in a light-emitting layer
• at least one dopant may be further comprised, and if necessary, another compound may be comprised as a second host material.
• the weight ratio between the first host material and the second host material is in the range of 1:99 to 99:1.
• the compound selected from the group consisting of the compounds of formulae 6 to 8 below is preferable as the known host material or the second host material in view of luminous efficiency.
• R 21 to R 24 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- 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
• the host materials represented by formulae 6 to 8 include the following:
• TPS triphenylsilyl
• the dopant is preferably at least one phosphorescent dopant.
• the phosphorescent dopant material for the organic electroluminescent device of the present disclosure is not limited, but may be preferably selected from metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) or platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) or platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
• the phosphorescent dopant may be preferably selected from the group consisting of compounds represented by the following formulae 9 to 11.
• 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, a cyano, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (C1-C30)alkoxy; or R 106 to R 109 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, a substituted or unsubstituted fluorene, a substituted or unsubstituted di
• the phosphorescent dopant material includes the following:
• a mixture or composition for preparing an organic electroluminescent device comprises the compound of the present disclosure.
• the mixture or composition may be a mixture or composition for preparing a light-emitting layer or a hole transport layer of an organic electroluminescent device.
• the compound of the present disclosure may be comprised as a host material.
• the mixture or composition may further comprise a second host material, for example, those selected from the compounds represented by formulae 6 to 8.
• the compound of the present disclosure may be comprised as a hole transport material.
• the organic electroluminescent device of the present disclosure may comprise a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes, wherein the organic layer may comprise a light-emitting layer or both a light-emitting layer and a hole transport layer, which may comprise the mixture or composition for preparing an organic electroluminescent device of the present disclosure.
• the organic electroluminescent device of the present disclosure 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 the metal.
• the organic layer may further comprise a light-emitting layer and a charge generating layer.
• the organic electroluminescent device of the present disclosure 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 art, besides the compound of the present disclosure.
• 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.
• 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 light-emitting 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 ink jet printing, nozzle printing, slot coating, 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.
• organic electroluminescent compound of the present disclosure the preparation method of the compound, and the luminescent properties of the device will be explained in detail with reference to the following examples.
• Compound 2-1 was prepared in the same manner as in Example 1 for the preparations of compounds 1-1 to 1-3, except for using 5-bromoindanone instead of 6-bromoindanone.
• OLED was produced using the material of the present disclosure as follows.
• a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) (Geomatec) was subjected to an ultrasonic washing with acetone and isopropanol, sequentially, and was then stored in isopropanol.
• the ITO substrate was then 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 -diphenylbenzene-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 10E -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-1 was then introduced into another cell of said vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
• compound H-1 as shown in Table 2 below 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, so that the dopant was 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.
• an OLED was produced. All the materials used for producing the OLED were those purified by vacuum sublimation at 10E -6 torr.
• the produced OLED showed green emission having a luminance of 1,500 cd/m 2 and a current density of 3.5 mA/cm 2 .
• OLED was produced in the same manner as in Device Example 1, except that compound C-71 was used to form a hole transport layer, and compounds H-2 and H-3 as shown in Table 2 below were used as a host.
• the produced OLED showed blue emission having a luminance of 700 cd/m 2 and a current density of 14.0 mA/cm 2 .
• OLED was produced in the same manner as in Device Example 1, except that compound C-89 was used to form a hole transport layer having a thickness of 20 nm.
• the produced OLED showed green emission having a luminance of 900 cd/m 2 and a current density of 1.9 mA/cm 2 .
• OLED was produced in the same manner as in Device Example 1, except that compound C-125 was used to form a hole transport layer, and compounds H-2 and H-3 were used as a host.
• the produced OLED showed blue emission having a luminance of 1,200 cd/m 2 and a current density of 25.0 mA/cm 2 .
• OLED was produced in the same manner as in Device Example 1, except that compound T-1 as shown in Table 2 below was used to form a hole transport layer having a thickness of 20 nm.
• the produced OLED showed green emission having a luminance of 9,800 cd/m 2 and a current density of 26.1 mA/cm 2 .
• OLED was produced in the same manner as in Device Example 1, except that compound T-1 was used to form a hole transport layer, and compounds H-2 and H-3 were used as a host.
• the produced OLED showed blue emission having a luminance of 2,800 cd/m 2 and a current density of 141.2 mA/cm 2 .
• the compound for organic electronic material of the present disclosure has better luminous characteristics than the conventional compounds.
• the organic electroluminescent device comprising the compound for organic electronic material of the present disclosure shows excellences in luminous characteristics and lifespan.

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