WO2016036171A1 - A plurality of host materials and organic electroluminescent devices comprising the same - Google Patents

A plurality of host materials and organic electroluminescent devices comprising the same Download PDF

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WO2016036171A1
WO2016036171A1 PCT/KR2015/009321 KR2015009321W WO2016036171A1 WO 2016036171 A1 WO2016036171 A1 WO 2016036171A1 KR 2015009321 W KR2015009321 W KR 2015009321W WO 2016036171 A1 WO2016036171 A1 WO 2016036171A1
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group
substituted
unsubstituted
alkyl
arylsilyl
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PCT/KR2015/009321
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French (fr)
Inventor
Bitnari Kim
Hong-Yeop NA
Nam-Kyun Kim
Tae-Jin Lee
Kyung-Hoon Choi
Young-Jun Cho
Young-Mook Lim
Hee-Ryong Kang
Doo-Hyeon Moon
Hyun-Ju Kang
Hee-Choon Ahn
Ji-Song JUN
Young-Kwang Kim
Jin-Ri HONG
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020150124312A external-priority patent/KR102409002B1/en
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Publication of WO2016036171A1 publication Critical patent/WO2016036171A1/en

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Definitions

  • the present disclosure relates to a plurality of host materials 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].
  • OLED organic electroluminescent device
  • electricity is applied to an organic light-emitting material which converts electric energy to light.
  • OLED has a structure comprising an anode, a cathode, and an organic layer disposed between the two electrodes.
  • the organic layer of OLED may comprise a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (comprising a host and dopant material), an electron buffering layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc.
  • a material for preparing the organic layer can be classified according to its function, as a hole injection material, a hole transport material, an electron blocking material, a light-emitting material, an electron buffering material, a hole blocking material, an electron transport material, an electron injection material, etc.
  • Holes and electrons are injected from an anode and a cathode, respectively, to the light-emitting layer by applying electricity to OLED; excitons having high energy are formed by recombinations between the holes and the electrons, which make organic light-emitting compounds be in an excited state, and the decay of the excited state results in a relaxation of the energy into a ground state, accompanied by light-emission.
  • the most important factor determining luminous efficiency in OLED is a light-emitting material.
  • the light-emitting material needs to have high quantum efficiency, high electron mobility, and high hole mobility.
  • the light-emitting layer formed by the light-emitting material needs to be uniform and stable. According to colors visualized by light-emission, the light-emitting material can be classified as a blue-, green-, or red-emitting material, and a yellow- or orange-emitting material can be additionally included therein. Furthermore, the light-emitting material can be classified according to its function, as a host material and a dopant material. Recently, the development of OLED providing high efficiency and long lifespan is urgent.
  • a host material which plays a role as a solvent in a solid state and transfers energy, should have high purity, and an appropriate molecular weight for being deposited under vacuum.
  • a host material should have high glass transition temperature and high thermal decomposition temperature to ensure thermal stability, high electrochemical stability to have long lifespan, ease of preparation for amorphous thin film, and good adhesion to materials of adjacent layers.
  • a host material should not move to an adjacent layer.
  • the light-emitting material can be prepared by combining a host with a dopant to improve color purity, luminous efficiency, and stability.
  • a device showing good EL performances comprises a light-emitting layer prepared by combining a host with a dopant.
  • the host material greatly influences the efficiency and lifespan of the EL device when using a host/dopant system, and thus its selection is important.
  • Korean Patent Appl. Laid-open No. 10-2008-0080306 discloses an organic electroluminescent device using a compound in which two carbazoles are linked through arylene, as a host material.
  • International Publication No. WO 2013/112557 A1 discloses an organic electroluminescent device using a compound in which a biscarbazole is linked with carbazole directly or using an arylene linker as a host material.
  • none of the literature above specifically discloses organic electroluminescent devices using a biscarbazole compound and the compound condensed of carbazole and quinoxaline as a plurality of host compounds.
  • the objective of the present disclosure is to provide an organic electroluminescent device having long lifespan while maintaining high luminous efficiency.
  • an organic electroluminescent device having at least one light-emitting layer disposed between an anode and a cathode, wherein the light-emitting layer comprises a host and a phosphorescent dopant, wherein the host consists of a plurality of host compounds, wherein at least a first host compound of a plurality of host compounds is represented by the following formula 1:
  • a 1 and A 2 each independently represent a substituted or unsubstituted (C6-C30)aryl group
  • L 1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene group
  • X 1 to X 16 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsily
  • a second host compound is represented by the following formula 2:
  • X and Y each independently represent CR 12 or N; provided that both X and Y are not CR 12 ;
  • R 1 to R 12 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri
  • the heteroaryl group contains at least one hetero atom selected from B, N, O, S, Si, and P.
  • an organic electroluminescent device having high luminous efficiency and long lifespan is provided.
  • the organic electroluminescent device of the present disclosure can be used for the manufacture of a display system or a lighting system.
  • the organic electroluminescent device comprising the organic electroluminescent compound of formulae 1 and 2 will be described in detail.
  • the compound of formula 1 may be represented by any one of the following formulae 3 to 6.
  • a 1 , A 2 , L 1 , and X 1 to X 16 are as defined in formula 1.
  • a 1 and A 2 in formula 1 each independently represent a substituted or unsubstituted (C6-C30)aryl group, and preferably, a substituted or unsubstituted (C6-C20)aryl group, and more preferably, a (C6-C20)aryl group unsubstituted or substituted with a cyano group, a halogen, a (C1-C6)alkyl group, a (C6-C12)aryl group, or tri(C6-C12)arylsilyl group.
  • a 1 and A 2 each independently may be selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted tetracenyl group, a substituted or unsubstituted peryleny
  • the substituent of the substituted group such as the substituted phenyl group may be a cyano group, a halogen group, a (C1-C6)alkyl group, a (C6-C12)aryl group, or a tri(C6-C12)arylsilyl group.
  • X 1 to X 16 in formula 1 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)ary
  • X 1 to X 16 each independently may represent hydrogen; a cyano group; a (C1-C6)alkyl group; phenyl, biphenyl, terphenyl, or naphthyl, unsubstituted or substituted with a cyano group, a (C1-C6)alkyl group or triphenylsilyl; dibenzothiophenyl or dibenzofuranyl, unsubstituted or substituted with a (C1-C6)alkyl group, phenyl, biphenyl, naphthyl, or triphenylsilyl; or triphenylsilyl unsubstituted or substituted with a (C1-C6)alkyl group.
  • L 1 in formula 1 represents a single bond or a substituted or unsubstituted (C6-C30)arylene group, and preferably, a single bond, or a substituted or unsubstituted (C6-C15)arylene group, and more preferably, a single bond, or a (C6-C15)arylene group unsubstituted or substituted with a cyano group, a (C1-C6)alkyl group, or a tri(C6-C12)arylsilyl group.
  • L 1 may represent any one of the following formulae 7 to 19.
  • Xi to Xp each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsily
  • Xi to Xp each independently represent hydrogen, a halogen, a cyano group, a (C1-C10)alkyl group, a (C3-C20)cycloalkyl group, a (C6-C12)aryl group, a (C1-C6)alkyldi(C6-C12)arylsilyl group, or a tri(C6-C12)arylsilyl group; and more preferably, hydrogen, a cyano group, a (C1-C6)alkyl group, or a tri(C6-C12)arylsilyl group.
  • the compound of formula 2 may be represented by any one of the following formulae 20 to 22:
  • R 1 to R 12 are as defined in formula 2 above.
  • X and Y in formula 2 each independently represent CR 12 or N; provided that both X and Y are not CR 12 .
  • R 1 to R 12 in formula 2 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstit
  • R 1 to R 12 each independently represent hydrogen; a (C6-C18)aryl group unsubstituted or substituted with methyl, (C6-C30)aryl group, or 5- to 30-membered heteroaryl group; or 5- to 30-membered heteroaryl group unsubstituted or substituted with methyl, (C6-C12)aryl group, or 5- to 15-membered heteroaryl group; or may be linked to an adjacent substituent(s) to form a benzene, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, indole, benzoindole, indene, or spiro[fluorine-indene], unsubstituted or substituted with methyl, (C6-C12)aryl group or 15- to 20-membered heteroaryl group.
  • the heteroaryl contains at least one hetero atom selected from B, N, O, S, Si, and P, and preferably, at least one hetero atom selected from N, O, and S.
  • (C1-C30)alkyl indicates a linear or branched alkyl having 1 to 30, preferably 1 to 20, and more 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, and 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, and 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, and more preferably 3 to 7 carbon atoms and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • “3- to 7-membered heterocycloalkyl” indicates a cycloalkyl having 3 to 7, preferably 5 to 7 ring backbone atoms including at least one hetero atom selected from B, N, O, S, Si, and P, preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.
  • (C6-C30)aryl(ene) indicates a monocyclic or fused ring-based radical derived from an aromatic hydrocarbon and having 6 to 30, preferably 6 to 20, and more preferably 6 to 15 ring backbone carbon atoms, 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.
  • “3- to 30-membered heteroaryl” indicates an aryl group having at least one, preferably 1 to 4, heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N, and 3 to 30 ring backbone atoms; is a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazan
  • the “nitrogen-containing 5- to 30-membered heteroaryl” indicates a heteroaryl group having 5 to 30, preferably 5 to 20, and more preferably 5 to 15 ring backbone atoms including at least one, preferably 1 to 4, nitrogen as the hetero atom; is a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl such as pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl such as benzoimidazolyl, isoindolyl,
  • 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 first host compound represented by formula 1 may be selected from the group consisting of the following compounds, but is not limited thereto:
  • the second host compound represented by formula 2 may be selected from the group consisting of the following compounds, but is not limited thereto:
  • the organic electroluminescent device of the present disclosure comprises an anode; a cathode; and at least one organic layer disposed between the anode and cathode, wherein the organic layer comprises one or more light-emitting layers; the light-emitting layer comprises a host and a phosphorescent dopant; the host consists of a plurality of host compounds; and a first host compound of a plurality of host compounds is represented by formula 1 and a second host compound is represented by formula 2.
  • the light-emitting layer indicates a layer from which light is emitted, and may be a single layer or a multiple layer deposited by two or more layers. It is preferable that a doping amount of the dopant compound is less than 20 wt% based on the total amount of the host compound and the dopant compound.
  • 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 electron buffering layer, an interlayer, a hole blocking layer, and an electron blocking layer.
  • the weight ratio in the light-emitting layer between the first host material and the second host material may be in the range of 1:99 to 99:1.
  • the dopant to be comprised in the organic electroluminescent device of the present disclosure 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) 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 dopant may be selected from the group consisting of compounds represented by the following formulae 101 to 103.
  • L is selected from the following structures:
  • R 100 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group;
  • R 101 to R 109 and R 111 to R 123 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group unsubstituted or substituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, a cyano group, or a substituted or unsubstituted (C1-C30)alkoxy group;
  • R 106 to R 109 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl group;
  • R 120 to R 123
  • R 124 to R 127 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C6-C30)aryl group; and R 124 to R 127 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl group, or a dibenzofuran unsubstituted or substituted with an alkyl group;
  • R 201 to R 211 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group unsubstituted or substituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl group, or a substituted or unsubstituted (C6-C30)aryl group; and R 208 to R 211 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl group, or a dibenzofuran unsubstituted or substituted with an alkyl group;
  • r and s each independently represent an integer of 1 to 3; when r or s is an integer of 2 or more, each of R 100 may be the same or different; and
  • e represents an integer of 1 to 3.
  • the phosphorescent dopant material includes the following:
  • the organic layer may further comprise 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 the d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
  • 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 hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be disposed between the anode and the light-emitting layer.
  • the hole injection layer may be composed of two or more layers in order to lower an energy barrier for injecting holes from the anode to a hole transport layer or an electron blocking layer (or a voltage for injecting a hole). Each of the layers may comprise two or more compounds.
  • the hole transport layer or electron blocking layer may be composed of two or more layers.
  • An electron buffering layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be disposed between the light-emitting layer and the cathode.
  • the electron buffering layer may be composed of two or more layers in order to control the electron injection and improve characteristics of interface between the light-emitting layer and the electron injection layer.
  • Each of the layers may comprise two or more compounds.
  • the hole blocking layer or electron transport layer may be composed of two or more layers, and each of the layers may comprise two or more compounds.
  • the hole blocking layer or electron transport layer may be composed of two or more layers, the each layer may be composed of two or more compounds.
  • 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, ion plating methods, etc.
  • wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating methods, etc.
  • 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.
  • two or more host compounds for a light-emitting layer may be co-evaporaton or mixture-evaporaton.
  • a co-evaporation indicates a process for two or more materials to be deposited as a mixture, by introducing each of the two or more materials into respective crucible cells, and applying electric current to the cells for each of the materials to be evaporated.
  • a mixture-evaporation indicates a process for two or more materials to be deposited as a mixture, by mixing the two or more materials in one crucible cell before the deposition, and applying electric current to the cell for the mixture to be evaporated.
  • the organic electroluminescent device of the present disclosure can be used for the manufacture of a display system or a lighting system.
  • OLED was produced using the light-emitting 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 electroluminescent device (OLED) (Geomatec) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water sequentially, and was then stored in isopropanol.
  • the ITO substrate was then mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • HI-1 was introduced into a cell of the vacuum vapor depositing apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -6 torr.
  • HI-1 a first hole injection layer having a thickness of 80 nm on the ITO substrate.
  • HI-2 was then introduced into another cell of the vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer.
  • HT-1 was introduced into one cell of the vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer.
  • HT-2 was then introduced into another cell of the vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer.
  • a light-emitting layer was then deposited as follows.
  • a host material a first host compound and a second host compound shown in Table 1 below were introduced into two cells of the vacuum vapor depositing apparatus, respectively.
  • a dopant compound D-71 was introduced into another cell.
  • the two host compounds were evaporated at the same rate of 1:1, while the dopant was evaporated at a different rate from the host compounds, so that the dopant was 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 40 nm on the hole transport layer.
  • ET-1 and EI-1 were introduced into two cells of the vacuum vapor depositing apparatus, respectively, and evaporated at the same rate of 1:1, thereby forming an electron transport layer having a thickness of 30 nm on the light-emitting layer.
  • an Al cathode having a thickness of 80 nm was then deposited by another vacuum vapor deposition apparatus on the electron injection layer.
  • an OLED was produced.
  • OLED was produced in the same manner as in Device Examples 1-1 to 1-12, except that only a second host compound shown in Table 1 below was used as a host for a light-emitting layer.
  • OLED was produced in the same manner as in Device Examples 1-1 to 1-12, except that only a first host compound shown in Table 1 below was used as a host for a light-emitting layer.
  • Comparing Device Examples 1-1 to 1-10 with Comparative Example 1-1, Device Example 1-11 with Comparative Example 1-2, and Device Example 1-12 with Comparative Example 1-3 it is shown that the OLED comprising a first host compound and a second host compound of the present disclosure has high efficiency and long lifespan compared with the OLED comprising a second host compound as a sole host. Also, comparing Device Examples 1-1, 1-11 and 1-12 with Comparative Example 2-1, and Device Example 1-7 with Comparative Example 2-2, it is shown that the OLED comprising a first host compound and a second host compound of the present disclosure has high efficiency and long lifespan compared with the OLED comprising a first host compound as a sole host.
  • the organic electroluminescent device comprising a light-emitting layer containing a host and a phosphorescent dopant can provide high luminous efficiency and long lifespan by comprising a plurality of host materials of the present disclosure.

Abstract

The present disclosure relates to a plurality of host materials and an organic electroluminescent device comprising the same. By comprising a specific combination of a plurality of host materials, the organic electroluminescent device of the present disclosure can show high luminous efficiency and long lifespan.

Description

A PLURALITY OF HOST MATERIALS AND ORGANIC ELECTROLUMINESCENT DEVICES COMPRISING THE SAME
The present disclosure relates to a plurality of host materials 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].
In an organic electroluminescent device (OLED), electricity is applied to an organic light-emitting material which converts electric energy to light. Generally, OLED has a structure comprising an anode, a cathode, and an organic layer disposed between the two electrodes. The organic layer of OLED may comprise a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (comprising a host and dopant material), an electron buffering layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. A material for preparing the organic layer can be classified according to its function, as a hole injection material, a hole transport material, an electron blocking material, a light-emitting material, an electron buffering material, a hole blocking material, an electron transport material, an electron injection material, etc. Holes and electrons are injected from an anode and a cathode, respectively, to the light-emitting layer by applying electricity to OLED; excitons having high energy are formed by recombinations between the holes and the electrons, which make organic light-emitting compounds be in an excited state, and the decay of the excited state results in a relaxation of the energy into a ground state, accompanied by light-emission.
The most important factor determining luminous efficiency in OLED is a light-emitting material. The light-emitting material needs to have high quantum efficiency, high electron mobility, and high hole mobility. Also, the light-emitting layer formed by the light-emitting material needs to be uniform and stable. According to colors visualized by light-emission, the light-emitting material can be classified as a blue-, green-, or red-emitting material, and a yellow- or orange-emitting material can be additionally included therein. Furthermore, the light-emitting material can be classified according to its function, as a host material and a dopant material. Recently, the development of OLED providing high efficiency and long lifespan is urgent. In particular, considering EL requirements for a middle or large-sized OLED panel, materials showing better performances than conventional ones must be urgently developed. In order to achieve the development, a host material which plays a role as a solvent in a solid state and transfers energy, should have high purity, and an appropriate molecular weight for being deposited under vacuum. In addition, a host material should have high glass transition temperature and high thermal decomposition temperature to ensure thermal stability, high electrochemical stability to have long lifespan, ease of preparation for amorphous thin film, and good adhesion to materials of adjacent layers. Furthermore, a host material should not move to an adjacent layer.
The light-emitting material can be prepared by combining a host with a dopant to improve color purity, luminous efficiency, and stability. Generally, a device showing good EL performances comprises a light-emitting layer prepared by combining a host with a dopant. The host material greatly influences the efficiency and lifespan of the EL device when using a host/dopant system, and thus its selection is important.
Korean Patent Appl. Laid-open No. 10-2008-0080306 discloses an organic electroluminescent device using a compound in which two carbazoles are linked through arylene, as a host material. International Publication No. WO 2013/112557 A1 discloses an organic electroluminescent device using a compound in which a biscarbazole is linked with carbazole directly or using an arylene linker as a host material. However, none of the literature above specifically discloses organic electroluminescent devices using a biscarbazole compound and the compound condensed of carbazole and quinoxaline as a plurality of host compounds.
The objective of the present disclosure is to provide an organic electroluminescent device having long lifespan while maintaining high luminous efficiency.
The present inventors found that the objective above can be achieved by an organic electroluminescent device having at least one light-emitting layer disposed between an anode and a cathode, wherein the light-emitting layer comprises a host and a phosphorescent dopant, wherein the host consists of a plurality of host compounds, wherein at least a first host compound of a plurality of host compounds is represented by the following formula 1:
Figure PCTKR2015009321-appb-I000001
wherein A1 and A2 each independently represent a substituted or unsubstituted (C6-C30)aryl group;
L1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene group;
X1 to X16 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino group; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted mono- or polycyclic (C3-C30), alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur; and
a second host compound is represented by the following formula 2:
Figure PCTKR2015009321-appb-I000002
wherein X and Y each independently represent CR12 or N; provided that both X and Y are not CR12;
R1 to R12 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino group, a substituted or unsubstituted mono- or di- (C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted mono- or polycyclic (C3-C30), alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur; and
the heteroaryl group contains at least one hetero atom selected from B, N, O, S, Si, and P.
According to the present disclosure, an organic electroluminescent device having high luminous efficiency and long lifespan is provided. In addition, the organic electroluminescent device of the present disclosure can be used for the manufacture of a display system or a lighting system.
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure, and is not meant in any way to restrict the scope of the present disclosure.
The organic electroluminescent device comprising the organic electroluminescent compound of formulae 1 and 2 will be described in detail.
The compound of formula 1 may be represented by any one of the following formulae 3 to 6.
Figure PCTKR2015009321-appb-I000003
Figure PCTKR2015009321-appb-I000004
Figure PCTKR2015009321-appb-I000005
Figure PCTKR2015009321-appb-I000006
wherein A1, A2, L1, and X1 to X16 are as defined in formula 1.
A1 and A2 in formula 1 each independently represent a substituted or unsubstituted (C6-C30)aryl group, and preferably, a substituted or unsubstituted (C6-C20)aryl group, and more preferably, a (C6-C20)aryl group unsubstituted or substituted with a cyano group, a halogen, a (C1-C6)alkyl group, a (C6-C12)aryl group, or tri(C6-C12)arylsilyl group. Specifically, A1 and A2 each independently may be selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted tetracenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted phenylnaphthyl group, a substituted or unsubstituted naphthylphenyl group, and a substituted or unsubstituted fluoranthenyl group. The substituent of the substituted group such as the substituted phenyl group may be a cyano group, a halogen group, a (C1-C6)alkyl group, a (C6-C12)aryl group, or a tri(C6-C12)arylsilyl group.
X1 to X16 in formula 1 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino group; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted mono- or polycyclic (C3-C30), alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur; and preferably, hydrogen, a cyano group, a substituted or unsubstituted (C1-C10)alkyl group, a substituted or unsubstituted (C6-C20)aryl group, a substituted or unsubstituted 5- to 20-membered heteroaryl group, or a substituted or unsubstituted tri(C6-C12)arylsilyl group; and more preferably, hydrogen; a cyano group; a (C1-C10)alkyl group; a (C6-C20)aryl group unsubstituted or substituted with a cyano group, a (C1-C10)alkyl group, or a tri(C6-C12)arylsilyl group; a 5- to 20-membered heteroaryl group unsubstituted or substituted with a (C1-C10)alkyl group, a (C6-C15)aryl group, or a tri(C6-C12)arylsilyl group; or a tri(C6-C12)arylsilyl group unsubstituted or substituted with a (C1-C10)alkyl group. Specifically, X1 to X16 each independently may represent hydrogen; a cyano group; a (C1-C6)alkyl group; phenyl, biphenyl, terphenyl, or naphthyl, unsubstituted or substituted with a cyano group, a (C1-C6)alkyl group or triphenylsilyl; dibenzothiophenyl or dibenzofuranyl, unsubstituted or substituted with a (C1-C6)alkyl group, phenyl, biphenyl, naphthyl, or triphenylsilyl; or triphenylsilyl unsubstituted or substituted with a (C1-C6)alkyl group.
L1 in formula 1 represents a single bond or a substituted or unsubstituted (C6-C30)arylene group, and preferably, a single bond, or a substituted or unsubstituted (C6-C15)arylene group, and more preferably, a single bond, or a (C6-C15)arylene group unsubstituted or substituted with a cyano group, a (C1-C6)alkyl group, or a tri(C6-C12)arylsilyl group.
Also, L1 may represent any one of the following formulae 7 to 19.
Figure PCTKR2015009321-appb-I000007
Figure PCTKR2015009321-appb-I000008
Figure PCTKR2015009321-appb-I000009
wherein Xi to Xp each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino group; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted mono- or polycyclic (C3-C30), alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from the group consisting of nitrogen, oxygen, and sulfur; and
Figure PCTKR2015009321-appb-I000010
represents a bonding site.
Preferably, Xi to Xp each independently represent hydrogen, a halogen, a cyano group, a (C1-C10)alkyl group, a (C3-C20)cycloalkyl group, a (C6-C12)aryl group, a (C1-C6)alkyldi(C6-C12)arylsilyl group, or a tri(C6-C12)arylsilyl group; and more preferably, hydrogen, a cyano group, a (C1-C6)alkyl group, or a tri(C6-C12)arylsilyl group.
The compound of formula 2 may be represented by any one of the following formulae 20 to 22:
Figure PCTKR2015009321-appb-I000011
wherein R1 to R12 are as defined in formula 2 above.
X and Y in formula 2 each independently represent CR12 or N; provided that both X and Y are not CR12.
R1 to R12 in formula 2 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino group, a substituted or unsubstituted mono- or di- (C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted mono- or polycyclic (C3-C30), alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur; and preferably, hydrogen, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted mono- or polycyclic (C5-C30), alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur. More preferably, R1 to R12 each independently represent hydrogen; a (C6-C18)aryl group unsubstituted or substituted with methyl, (C6-C30)aryl group, or 5- to 30-membered heteroaryl group; or 5- to 30-membered heteroaryl group unsubstituted or substituted with methyl, (C6-C12)aryl group, or 5- to 15-membered heteroaryl group; or may be linked to an adjacent substituent(s) to form a benzene, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, indole, benzoindole, indene, or spiro[fluorine-indene], unsubstituted or substituted with methyl, (C6-C12)aryl group or 15- to 20-membered heteroaryl group.
The heteroaryl contains at least one hetero atom selected from B, N, O, S, Si, and P, and preferably, at least one hetero atom selected from N, O, and S.
Herein, “(C1-C30)alkyl” indicates a linear or branched alkyl having 1 to 30, preferably 1 to 20, and more 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, and 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, and 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, and more preferably 3 to 7 carbon atoms and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. “3- to 7-membered heterocycloalkyl” indicates a cycloalkyl having 3 to 7, preferably 5 to 7 ring backbone atoms including at least one hetero atom selected from B, N, O, S, Si, and P, preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. Furthermore, “(C6-C30)aryl(ene)” indicates a monocyclic or fused ring-based radical derived from an aromatic hydrocarbon and having 6 to 30, preferably 6 to 20, and more preferably 6 to 15 ring backbone carbon atoms, 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. “3- to 30-membered heteroaryl” indicates an aryl group having at least one, preferably 1 to 4, heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N, and 3 to 30 ring backbone atoms; is a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, etc. The “nitrogen-containing 5- to 30-membered heteroaryl” indicates a heteroaryl group having 5 to 30, preferably 5 to 20, and more preferably 5 to 15 ring backbone atoms including at least one, preferably 1 to 4, nitrogen as the hetero atom; is a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl such as pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl such as benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenanthridinyl, etc. Furthermore, “halogen” includes F, Cl, Br, and I.
Herein, “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. In A1, A2, L1, X1 to X16, and R1 to R12 in formulae 1 and 2, the substituents of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, the substituted aryl(ene) group, the substituted heteroaryl group, the substituted cycloalkyl group, the substituted alkoxy group, the substituted trialkylsilyl group, the substituted dialkylarylsilyl group, the substituted alkyldiarylsilyl group, the substituted triarylsilyl group, the substituted mono- or di-alkylamino group, the substituted mono- or di-arylamino group, the substituted alkylarylamino group, and the substituted mono- or polycyclic, alicyclic or aromatic ring are each independently at least one selected from the group consisting of deuterium; a halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; a (C1-C30)alkyl group; a halo(C1-C30)alkyl group; a (C2-C30)alkenyl group; a (C2-C30)alkynyl group; a (C1-C30)alkoxy group; a (C1-C30)alkylthio group; a (C3-C30)cycloalkyl group; a (C3-C30)cycloalkenyl group; a 3- to 7-membered heterocycloalkyl group; a (C6-C30)aryloxy group; a (C6-C30)arylthio group; a 3- to 30-membered heteroaryl group unsubstituted or substituted with a (C6-C30)aryl group or a di(C6-C30)arylamino group; a (C6-C30)aryl group unsubstituted or substituted with a cyano group, a 3- to 30-membered heteroaryl group or a tri(C6-C30)arylsilyl group; a tri(C1-C30)alkylsilyl group; a tri(C6-C30)arylsilyl group; a di(C1-C30)alkyl(C6-C30)arylsilyl group; a (C1-C30)alkyldi(C6-C30)arylsilyl group; an amino group; a mono- or di- (C1-C30)alkylamino group; a mono- or di- (C6-C30)arylamino group; a (C1-C30)alkyl(C6-C30)arylamino group; a (C1-C30)alkylcarbonyl group; a (C1-C30)alkoxycarbonyl group; a (C6-C30)arylcarbonyl group; a di(C6-C30)arylboronyl group; a di(C1-C30)alkylboronyl group; a (C1-C30)alkyl(C6-C30)arylboronyl group; a (C6-C30)aryl(C1-C30)alkyl group; and a (C1-C30)alkyl(C6-C30)aryl group; and preferably, at least one selected from the group consisting of a halogen; a cyano group; a (C1-C6)alkyl group; a 5- to 30-membered heteroaryl group; a (C6-C30)aryl group unsubstituted or substituted with a cyano group or a tri(C6-C12)arylsilyl group; a tri(C6-C12)arylsilyl group; and a (C1-C6)alkyldi(C6-C12)aryl group.
The first host compound represented by formula 1 may be selected from the group consisting of the following compounds, but is not limited thereto:
Figure PCTKR2015009321-appb-I000012
Figure PCTKR2015009321-appb-I000013
Figure PCTKR2015009321-appb-I000014
Figure PCTKR2015009321-appb-I000015
Figure PCTKR2015009321-appb-I000016
Figure PCTKR2015009321-appb-I000017
Figure PCTKR2015009321-appb-I000018
Figure PCTKR2015009321-appb-I000019
Figure PCTKR2015009321-appb-I000020
Figure PCTKR2015009321-appb-I000021
Figure PCTKR2015009321-appb-I000022
Figure PCTKR2015009321-appb-I000023
Figure PCTKR2015009321-appb-I000024
Figure PCTKR2015009321-appb-I000025
Figure PCTKR2015009321-appb-I000026
Figure PCTKR2015009321-appb-I000027
Figure PCTKR2015009321-appb-I000028
Figure PCTKR2015009321-appb-I000029
Figure PCTKR2015009321-appb-I000030
Figure PCTKR2015009321-appb-I000031
Figure PCTKR2015009321-appb-I000032
Figure PCTKR2015009321-appb-I000033
Figure PCTKR2015009321-appb-I000034
Figure PCTKR2015009321-appb-I000035
Figure PCTKR2015009321-appb-I000036
Figure PCTKR2015009321-appb-I000037
Figure PCTKR2015009321-appb-I000038
Figure PCTKR2015009321-appb-I000039
Figure PCTKR2015009321-appb-I000040
Figure PCTKR2015009321-appb-I000041
Figure PCTKR2015009321-appb-I000042
Figure PCTKR2015009321-appb-I000043
Figure PCTKR2015009321-appb-I000044
Figure PCTKR2015009321-appb-I000045
Figure PCTKR2015009321-appb-I000046
Figure PCTKR2015009321-appb-I000047
Figure PCTKR2015009321-appb-I000048
Figure PCTKR2015009321-appb-I000049
Figure PCTKR2015009321-appb-I000050
Figure PCTKR2015009321-appb-I000051
Figure PCTKR2015009321-appb-I000052
Figure PCTKR2015009321-appb-I000053
Figure PCTKR2015009321-appb-I000054
Figure PCTKR2015009321-appb-I000055
Figure PCTKR2015009321-appb-I000056
Figure PCTKR2015009321-appb-I000057
Figure PCTKR2015009321-appb-I000058
Figure PCTKR2015009321-appb-I000059
Figure PCTKR2015009321-appb-I000060
Figure PCTKR2015009321-appb-I000061
Figure PCTKR2015009321-appb-I000062
Figure PCTKR2015009321-appb-I000063
Figure PCTKR2015009321-appb-I000064
The second host compound represented by formula 2 may be selected from the group consisting of the following compounds, but is not limited thereto:
Figure PCTKR2015009321-appb-I000065
Figure PCTKR2015009321-appb-I000066
Figure PCTKR2015009321-appb-I000067
Figure PCTKR2015009321-appb-I000068
Figure PCTKR2015009321-appb-I000069
Figure PCTKR2015009321-appb-I000070
Figure PCTKR2015009321-appb-I000071
Figure PCTKR2015009321-appb-I000072
Figure PCTKR2015009321-appb-I000073
Figure PCTKR2015009321-appb-I000074
Figure PCTKR2015009321-appb-I000075
Figure PCTKR2015009321-appb-I000076
Figure PCTKR2015009321-appb-I000077
Figure PCTKR2015009321-appb-I000078
Figure PCTKR2015009321-appb-I000079
Figure PCTKR2015009321-appb-I000080
Figure PCTKR2015009321-appb-I000081
Figure PCTKR2015009321-appb-I000082
Figure PCTKR2015009321-appb-I000083
Figure PCTKR2015009321-appb-I000084
Figure PCTKR2015009321-appb-I000085
Figure PCTKR2015009321-appb-I000086
Figure PCTKR2015009321-appb-I000087
Figure PCTKR2015009321-appb-I000088
Figure PCTKR2015009321-appb-I000089
Figure PCTKR2015009321-appb-I000090
Figure PCTKR2015009321-appb-I000091
Figure PCTKR2015009321-appb-I000092
Figure PCTKR2015009321-appb-I000093
Figure PCTKR2015009321-appb-I000094
Figure PCTKR2015009321-appb-I000095
Figure PCTKR2015009321-appb-I000096
Figure PCTKR2015009321-appb-I000097
Figure PCTKR2015009321-appb-I000098
Figure PCTKR2015009321-appb-I000099
Figure PCTKR2015009321-appb-I000100
Figure PCTKR2015009321-appb-I000101
Figure PCTKR2015009321-appb-I000102
Figure PCTKR2015009321-appb-I000103
Figure PCTKR2015009321-appb-I000104
Figure PCTKR2015009321-appb-I000105
Figure PCTKR2015009321-appb-I000106
Figure PCTKR2015009321-appb-I000107
Figure PCTKR2015009321-appb-I000108
Figure PCTKR2015009321-appb-I000109
Figure PCTKR2015009321-appb-I000110
Figure PCTKR2015009321-appb-I000111
The organic electroluminescent device of the present disclosure comprises an anode; a cathode; and at least one organic layer disposed between the anode and cathode, wherein the organic layer comprises one or more light-emitting layers; the light-emitting layer comprises a host and a phosphorescent dopant; the host consists of a plurality of host compounds; and a first host compound of a plurality of host compounds is represented by formula 1 and a second host compound is represented by formula 2.
The light-emitting layer indicates a layer from which light is emitted, and may be a single layer or a multiple layer deposited by two or more layers. It is preferable that a doping amount of the dopant compound is less than 20 wt% based on the total amount of the host compound and the dopant compound.
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 electron buffering layer, an interlayer, a hole blocking layer, and an electron blocking layer.
In the organic electroluminescent device of the present disclosure, the weight ratio in the light-emitting layer between the first host material and the second host material may be in the range of 1:99 to 99:1.
The dopant to be comprised in the organic electroluminescent device of the present disclosure 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) 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.
Preferably, the phosphorescent dopant may be selected from the group consisting of compounds represented by the following formulae 101 to 103.
Figure PCTKR2015009321-appb-I000112
Figure PCTKR2015009321-appb-I000113
Figure PCTKR2015009321-appb-I000114
wherein L is selected from the following structures:
Figure PCTKR2015009321-appb-I000115
R100 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group;
R101 to R109 and R111 to R123 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group unsubstituted or substituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, a cyano group, or a substituted or unsubstituted (C1-C30)alkoxy group; R106 to R109 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl group; R120 to R123 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, a quinoline unsubstituted or substituted with an alkyl or aryl;
R124 to R127 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C6-C30)aryl group; and R124 to R127 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl group, or a dibenzofuran unsubstituted or substituted with an alkyl group;
R201 to R211 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group unsubstituted or substituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl group, or a substituted or unsubstituted (C6-C30)aryl group; and R208 to R211 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl group, or a dibenzofuran unsubstituted or substituted with an alkyl group;
r and s each independently represent an integer of 1 to 3; when r or s is an integer of 2 or more, each of R100 may be the same or different; and
e represents an integer of 1 to 3.
Specifically, the phosphorescent dopant material includes the following:
Figure PCTKR2015009321-appb-I000116
Figure PCTKR2015009321-appb-I000117
Figure PCTKR2015009321-appb-I000118
Figure PCTKR2015009321-appb-I000119
Figure PCTKR2015009321-appb-I000120
Figure PCTKR2015009321-appb-I000121
Figure PCTKR2015009321-appb-I000122
Figure PCTKR2015009321-appb-I000123
Figure PCTKR2015009321-appb-I000124
Figure PCTKR2015009321-appb-I000125
Figure PCTKR2015009321-appb-I000126
Figure PCTKR2015009321-appb-I000127
Figure PCTKR2015009321-appb-I000128
Figure PCTKR2015009321-appb-I000129
Figure PCTKR2015009321-appb-I000130
Figure PCTKR2015009321-appb-I000131
Figure PCTKR2015009321-appb-I000132
Figure PCTKR2015009321-appb-I000133
Figure PCTKR2015009321-appb-I000134
Figure PCTKR2015009321-appb-I000135
Figure PCTKR2015009321-appb-I000136
Figure PCTKR2015009321-appb-I000137
Figure PCTKR2015009321-appb-I000138
Figure PCTKR2015009321-appb-I000139
Figure PCTKR2015009321-appb-I000140
In the organic electroluminescent device of the present disclosure, the organic layer may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
In the organic electroluminescent device of the present disclosure, 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 4th period, transition metals of the 5th period, lanthanides and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
Preferably, in the organic electroluminescent device of the present disclosure, at least one layer (hereinafter, "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. Specifically, a chalcogenide (includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer, and 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. Preferably, the chalcogenide includes SiOX (1≤X≤2), AlOX (1≤X≤1.5), SiON, SiAlON, etc.; the metal halide includes LiF, MgF2, CaF2, a rare earth metal fluoride, etc.; and the metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be disposed between the anode and the light-emitting layer. The hole injection layer may be composed of two or more layers in order to lower an energy barrier for injecting holes from the anode to a hole transport layer or an electron blocking layer (or a voltage for injecting a hole). Each of the layers may comprise two or more compounds. The hole transport layer or electron blocking layer may be composed of two or more layers.
An electron buffering layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be disposed between the light-emitting layer and the cathode. The electron buffering layer may be composed of two or more layers in order to control the electron injection and improve characteristics of interface between the light-emitting layer and the electron injection layer. Each of the layers may comprise two or more compounds. The hole blocking layer or electron transport layer may be composed of two or more layers, and each of the layers may comprise two or more compounds. The hole blocking layer or electron transport layer may be composed of two or more layers, the each layer may be composed of two or more compounds.
In the organic electroluminescent device of the present disclosure, 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. In this case, 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. Furthermore, 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. Preferably, 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 light-emitting layers and emitting white light.
In order to form each layer of the organic electroluminescent device of the present disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc., or wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating methods, etc., can be used.
When using a wet film-forming method, 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.
In the organic electroluminescent device of the present disclosure, two or more host compounds for a light-emitting layer may be co-evaporaton or mixture-evaporaton.
A co-evaporation indicates a process for two or more materials to be deposited as a mixture, by introducing each of the two or more materials into respective crucible cells, and applying electric current to the cells for each of the materials to be evaporated. Herein, a mixture-evaporation indicates a process for two or more materials to be deposited as a mixture, by mixing the two or more materials in one crucible cell before the deposition, and applying electric current to the cell for the mixture to be evaporated.
Also, the organic electroluminescent device of the present disclosure can be used for the manufacture of a display system or a lighting system.
Hereinafter, the luminescent properties of the device comprising the host compound of the present disclosure will be explained in detail with reference to the following examples.
[Device Examples 1-1 to 1-12] Production of OLED by a co-evaporation of a first host compound and a second host compound of the present disclosure
OLED was produced using the light-emitting material of the present disclosure as follows. A transparent electrode indium tin oxide (ITO) thin film (10 Ω/sq) on a glass substrate for an organic electroluminescent device (OLED) (Geomatec) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water sequentially, and was then stored in isopropanol. The ITO substrate was then mounted on a substrate holder of a vacuum vapor depositing apparatus. HI-1 was introduced into a cell of the vacuum vapor depositing apparatus, and then the pressure in the chamber of the apparatus was controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate HI-1, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate. HI-2 was then introduced into another cell of the vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer. HT-1 was introduced into one cell of the vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer. HT-2 was then introduced into another cell of the vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After forming the hole injection layers and the hole transport layers, a light-emitting layer was then deposited as follows. As a host material, a first host compound and a second host compound shown in Table 1 below were introduced into two cells of the vacuum vapor depositing apparatus, respectively. A dopant compound D-71 was introduced into another cell. The two host compounds were evaporated at the same rate of 1:1, while the dopant was evaporated at a different rate from the host compounds, so that the dopant was 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 40 nm on the hole transport layer. ET-1 and EI-1 were introduced into two cells of the vacuum vapor depositing apparatus, respectively, and evaporated at the same rate of 1:1, thereby forming an electron transport layer having a thickness of 30 nm on the light-emitting layer. After depositing EI-1 having a thickness of 2 nm as an electron injection layer on the electron transport layer, an Al cathode having a thickness of 80 nm was then deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED was produced.
Figure PCTKR2015009321-appb-I000141
[Comparative Examples 1-1 to 1-3] Production of OLED using a second host compound as a sole host
OLED was produced in the same manner as in Device Examples 1-1 to 1-12, except that only a second host compound shown in Table 1 below was used as a host for a light-emitting layer.
[Comparative Examples 2-1 and 2-2] Production of OLED using a first host compound as a sole host
OLED was produced in the same manner as in Device Examples 1-1 to 1-12, except that only a first host compound shown in Table 1 below was used as a host for a light-emitting layer.
The characteristics of the organic electroluminescent devices produced in device examples 1-1 to 1-12, comparative examples 1-1 to 1-3, and comparative examples 2-1 and 2-2 are shown in Table 1 below.
Figure PCTKR2015009321-appb-I000142
Figure PCTKR2015009321-appb-I000143
Comparing Device Examples 1-1 to 1-10 with Comparative Example 1-1, Device Example 1-11 with Comparative Example 1-2, and Device Example 1-12 with Comparative Example 1-3, it is shown that the OLED comprising a first host compound and a second host compound of the present disclosure has high efficiency and long lifespan compared with the OLED comprising a second host compound as a sole host. Also, comparing Device Examples 1-1, 1-11 and 1-12 with Comparative Example 2-1, and Device Example 1-7 with Comparative Example 2-2, it is shown that the OLED comprising a first host compound and a second host compound of the present disclosure has high efficiency and long lifespan compared with the OLED comprising a first host compound as a sole host.
The organic electroluminescent device comprising a light-emitting layer containing a host and a phosphorescent dopant can provide high luminous efficiency and long lifespan by comprising a plurality of host materials of the present disclosure.

Claims (7)

  1. An organic electroluminescent device having at least one light-emitting layer disposed between an anode and a cathode, wherein the light-emitting layer comprises a host and a phosphorescent dopant, wherein the host consists of a plurality of host compounds, wherein at least a first host compound of a plurality of host compounds is represented by the following formula 1:
    Figure PCTKR2015009321-appb-I000144
    wherein A1 and A2 each independently represent a substituted or unsubstituted (C6-C30)aryl group;
    L1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene group;
    X1 to X16 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino group; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted mono- or polycyclic (C3-C30), alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur; and
    a second host compound is represented by the following formula 2:
    Figure PCTKR2015009321-appb-I000145
    wherein X and Y each independently represent CR12 or N; provided that both X and Y are not CR12;
    R1 to R12 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted mono- or polycyclic (C3-C30), alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur; and
    the heteroaryl group contains at least one hetero atom selected from B, N, O, S, Si, and P.
  2. The organic electroluminescent device according to claim 1, wherein the compound of formula 1 is represented by any one of the following formulae 3 to 6.
    Figure PCTKR2015009321-appb-I000146
    Figure PCTKR2015009321-appb-I000147
    Figure PCTKR2015009321-appb-I000148
    Figure PCTKR2015009321-appb-I000149
    wherein A1, A2, L1, and X1 to X16 are as defined in claim 1.
  3. The organic electroluminescent device according to claim 1, wherein L1 of formula 1 is represented by any one of the following formulae 7 to 19.
    Figure PCTKR2015009321-appb-I000150
    Figure PCTKR2015009321-appb-I000151
    Figure PCTKR2015009321-appb-I000152
    wherein Xi to Xp each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino group; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted mono- or polycyclic (C3-C30), alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from the group consisting of nitrogen, oxygen, and sulfur.
  4. The organic electroluminescent compound according to claim 1, wherein the compound of formula 2 is represented by any one of the following formulae 20 to 22.
    Figure PCTKR2015009321-appb-I000153
    wherein R1 to R12 are as defined in claim 1.
  5. The organic electroluminescent compound according to claim 1, wherein the substituents of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, the substituted aryl(ene) group, the substituted heteroaryl group, the substituted cycloalkyl group, the substituted alkoxy group, the substituted trialkylsilyl group, the substituted dialkylarylsilyl group, the substituted alkyldiarylsilyl group, the substituted triarylsilyl group, the substituted mono- or di-alkylamino group, the substituted mono- or di-arylamino group, the substituted alkylarylamino group, and the substituted mono- or polycyclic alicyclic or aromatic ring in A1, A2, L1, X1 to X16, and R1 to R12 each independently are at least one selected from the group consisting of deuterium; a halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; a (C1-C30)alkyl group; a halo(C1-C30)alkyl group; a (C2-C30)alkenyl group; a (C2-C30)alkynyl group; a (C1-C30)alkoxy group; a (C1-C30)alkylthio group; a (C3-C30)cycloalkyl group; a 3- to 7-membered heterocycloalkyl group; a (C6-C30)aryloxy group; a (C6-C30)arylthio group; a 3- to 30-membered heteroaryl group unsubstituted or substituted with a (C6-C30)aryl group or a di(C6-C30)arylamino group; a (C6-C30)aryl group unsubstituted or substituted with a 3- to 30-membered heteroaryl group or a di(C6-C30)arylamino group; a tri(C1-C30)alkylsilyl group; a tri(C6-C30)arylsilyl group; a di(C1-C30)alkyl(C6-C30)arylsilyl group; a (C1-C30)alkyldi(C6-C30)arylsilyl group; an amino group; a mono- or di- (C1-C30)alkylamino group; a mono- or di- (C6-C30)arylamino group; a (C1-C30)alkyl(C6-C30)arylamino group; a (C1-C30)alkylcarbonyl group; a (C1-C30)alkoxycarbonyl group; a (C6-C30)arylcarbonyl group; a di(C6-C30)arylboronyl group; a di(C1-C30)alkylboronyl group; a (C1-C30)alkyl(C6-C30)arylboronyl group; a (C6-C30)aryl(C1-C30)alkyl group; and a (C1-C30)alkyl(C6-C30)aryl group.
  6. The organic electroluminescent compound according to claim 1, wherein the compound of formula 1 is selected from the group consisting of:
    Figure PCTKR2015009321-appb-I000154
    Figure PCTKR2015009321-appb-I000155
    Figure PCTKR2015009321-appb-I000156
    Figure PCTKR2015009321-appb-I000157
    Figure PCTKR2015009321-appb-I000158
    Figure PCTKR2015009321-appb-I000159
    Figure PCTKR2015009321-appb-I000160
    Figure PCTKR2015009321-appb-I000161
    Figure PCTKR2015009321-appb-I000162
    Figure PCTKR2015009321-appb-I000163
    Figure PCTKR2015009321-appb-I000164
    Figure PCTKR2015009321-appb-I000165
    Figure PCTKR2015009321-appb-I000166
    Figure PCTKR2015009321-appb-I000167
    Figure PCTKR2015009321-appb-I000168
    Figure PCTKR2015009321-appb-I000169
    Figure PCTKR2015009321-appb-I000170
    Figure PCTKR2015009321-appb-I000171
    Figure PCTKR2015009321-appb-I000172
    Figure PCTKR2015009321-appb-I000173
    Figure PCTKR2015009321-appb-I000174
    Figure PCTKR2015009321-appb-I000175
    Figure PCTKR2015009321-appb-I000176
    Figure PCTKR2015009321-appb-I000177
    Figure PCTKR2015009321-appb-I000178
    Figure PCTKR2015009321-appb-I000179
    Figure PCTKR2015009321-appb-I000180
    Figure PCTKR2015009321-appb-I000181
    Figure PCTKR2015009321-appb-I000182
    Figure PCTKR2015009321-appb-I000183
    Figure PCTKR2015009321-appb-I000184
    Figure PCTKR2015009321-appb-I000185
    Figure PCTKR2015009321-appb-I000186
    Figure PCTKR2015009321-appb-I000187
    Figure PCTKR2015009321-appb-I000188
    Figure PCTKR2015009321-appb-I000189
    Figure PCTKR2015009321-appb-I000190
    Figure PCTKR2015009321-appb-I000191
    Figure PCTKR2015009321-appb-I000192
    Figure PCTKR2015009321-appb-I000193
    Figure PCTKR2015009321-appb-I000194
    Figure PCTKR2015009321-appb-I000195
    Figure PCTKR2015009321-appb-I000196
    Figure PCTKR2015009321-appb-I000197
    Figure PCTKR2015009321-appb-I000198
    Figure PCTKR2015009321-appb-I000199
    Figure PCTKR2015009321-appb-I000200
    Figure PCTKR2015009321-appb-I000201
    Figure PCTKR2015009321-appb-I000202
    Figure PCTKR2015009321-appb-I000203
    Figure PCTKR2015009321-appb-I000204
    Figure PCTKR2015009321-appb-I000205
    Figure PCTKR2015009321-appb-I000206
  7. The organic electroluminescent compound according to claim 1, wherein the compound of formula 2 is selected from the group consisting of:
    Figure PCTKR2015009321-appb-I000207
    Figure PCTKR2015009321-appb-I000208
    Figure PCTKR2015009321-appb-I000209
    Figure PCTKR2015009321-appb-I000210
    Figure PCTKR2015009321-appb-I000211
    Figure PCTKR2015009321-appb-I000212
    Figure PCTKR2015009321-appb-I000213
    Figure PCTKR2015009321-appb-I000214
    Figure PCTKR2015009321-appb-I000215
    Figure PCTKR2015009321-appb-I000216
    Figure PCTKR2015009321-appb-I000217
    Figure PCTKR2015009321-appb-I000218
    Figure PCTKR2015009321-appb-I000219
    Figure PCTKR2015009321-appb-I000220
    Figure PCTKR2015009321-appb-I000221
    Figure PCTKR2015009321-appb-I000222
    Figure PCTKR2015009321-appb-I000223
    Figure PCTKR2015009321-appb-I000224
    Figure PCTKR2015009321-appb-I000225
    Figure PCTKR2015009321-appb-I000226
    Figure PCTKR2015009321-appb-I000227
    Figure PCTKR2015009321-appb-I000228
    Figure PCTKR2015009321-appb-I000229
    Figure PCTKR2015009321-appb-I000230
    Figure PCTKR2015009321-appb-I000231
    Figure PCTKR2015009321-appb-I000232
    Figure PCTKR2015009321-appb-I000233
    Figure PCTKR2015009321-appb-I000234
    Figure PCTKR2015009321-appb-I000235
    Figure PCTKR2015009321-appb-I000236
    Figure PCTKR2015009321-appb-I000237
    Figure PCTKR2015009321-appb-I000238
    Figure PCTKR2015009321-appb-I000239
    Figure PCTKR2015009321-appb-I000240
    Figure PCTKR2015009321-appb-I000241
    Figure PCTKR2015009321-appb-I000242
    Figure PCTKR2015009321-appb-I000243
    Figure PCTKR2015009321-appb-I000244
    Figure PCTKR2015009321-appb-I000245
    Figure PCTKR2015009321-appb-I000246
    Figure PCTKR2015009321-appb-I000247
    Figure PCTKR2015009321-appb-I000248
    Figure PCTKR2015009321-appb-I000249
    Figure PCTKR2015009321-appb-I000250
    Figure PCTKR2015009321-appb-I000251
    Figure PCTKR2015009321-appb-I000252
    Figure PCTKR2015009321-appb-I000253
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