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WO2015056993A1 - Combination of a host compound and a dopant compound and organic electroluminescent device comprising the same - Google Patents

Combination of a host compound and a dopant compound and organic electroluminescent device comprising the same Download PDF

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Publication number
WO2015056993A1
WO2015056993A1 PCT/KR2014/009734 KR2014009734W WO2015056993A1 WO 2015056993 A1 WO2015056993 A1 WO 2015056993A1 KR 2014009734 W KR2014009734 W KR 2014009734W WO 2015056993 A1 WO2015056993 A1 WO 2015056993A1
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Prior art keywords
substituted
unsubstituted
alkyl
membered
aryl
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Inventor
Kyung-Joo Lee
Seok-Keun Yoon
Chi-Sik Kim
Hyun Kim
Seon-Woo Lee
So-Young Jung
Su-Hyun Lee
Jeong-Eun YANG
Young-Kwang Kim
Young-Jun Cho
Kyoung-Jin Park
Sung-Woo Jang
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DuPont Specialty Materials Korea Ltd
DuPont Electronic Materials International LLC
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Rohm and Haas Electronic Materials Korea Ltd
Rohm and Haas Electronic Materials LLC
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Priority to CN201480055117.8A priority Critical patent/CN105636971A/en
Publication of WO2015056993A1 publication Critical patent/WO2015056993A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Definitions

  • the present disclosure relates to a combination of a host compound and a dopant 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].
  • an organic EL device has a structure comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode.
  • the organic layer of the organic EL device comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc.
  • Excitons having high energy are formed by recombinations between the holes and the electrons, the energy puts the light-emitting organic compound in an excited state, and the decay of the excited state results in a relaxation of the energy level into a ground state, accompanied by light-emission.
  • the most important factor determining luminous efficiency in the organic EL device is light-emitting materials.
  • 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.
  • the light-emitting materials can be classified as a blue-, green-, or red-emitting material, and a yellow- or orange-emitting material can be additionally included therein.
  • the light-emitting materials can be classified as a host material and a dopant material.
  • devices showing the best electroluminescent characteristics comprise a light-emitting layer in which a dopant is doped into a host, in general. Furthermore, depending on the excited state, the light-emitting material can be classified as fluorescent materials (singlet state) and phosphorescent materials (triplet state). Fluorescent materials have been widely used for the organic EL device. However, since phosphorescent materials enhance luminous efficiency for converting electricity to light by four (4) times compared to fluorescent materials and can reduce power consumption to have longer lifespan, development of phosphorescent light-emitting materials are widely being researched.
  • Iridium(III) complexes have been widely known as phosphorescent dopant 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)
  • phosphorescent host materials provide good light-emitting characteristics, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, their degradation may occur during a high-temperature deposition process in a vacuum. (2) The power efficiency of the organic EL device is given by [( ⁇ /voltage) ⁇ current efficiency], and the power efficiency is inversely proportional to the voltage. Although the organic EL device comprising phosphorescent host materials provides higher current efficiency (cd/A) than one comprising fluorescent host materials, a significantly high driving voltage is necessary. Thus, there is no merit in terms of power efficiency (lm/W). (3) Furthermore, the operational lifespan of the organic EL device is short, and luminous efficiency is still required to be improved.
  • Korean Patent Application Laying-open No. 10-2011-0130475 discloses iridium complexes for being used as a dopant compound of an organic electroluminescent device, and compounds having triphenylene moiety and dibenzothiophene moiety as a host compound suitable for being combined with the iridium complexes.
  • Korean Patent Application Laying-open No. 10-2011-0015836 discloses organic electroluminescent compounds having a carbazole moiety, and a combination of said compound and Ir(ppy) 3 or (piq) 2 Ir(acac) [bis-(1-phenylisoquinolyl)iridium(III) acetylacetonate].
  • the conventional combination of a dopant compound and a host compound is applied to an organic electroluminescent device, the characteristics such as a driving voltage, luminous efficiency, and power efficiency are not satisfactory.
  • the present inventors found that when using a combination of a specific iridium complex and a specific carbazole-containing compound as a light-emitting material, it is possible to produce an organic electroluminescent device showing excellence in luminous and power efficiencies at a low driving voltage.
  • the objective of the present disclosure is to provide a combination of a dopant compound and a host compound, which can provide excellent luminous and power efficiencies, long lifespan, and a lowered driving voltage; and an organic electroluminescent device showing long lifespan, excellent luminous and power efficiencies, and a low driving voltage by comprising the combination.
  • the present inventors found that the above objective can be achieved by a combination of one or more dopant compounds represented by the following formula 1 and one or more host compounds represented by the following formula 2, and an organic electroluminescent device comprising the same.
  • L 1 to L 3 are selected from the following structures A-1 to A-5, with the proviso that at least one of L 1 to L 3 is represented by A-1, A-2 or A-3:
  • X represents O or S
  • R 1 to R 11 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; and
  • a to h each independently, represent an integer of 0 to 4; where a, b, c, d, e, f, g, or h is an integer of 2 or more, each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , or R 8 may be the same or different,
  • Y 1 represents O, S, -NR 31 or -CR 32 R 33 ;
  • L 4 and L 5 each independently, represent a single bond, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
  • R 21 to R 24 each independently, represent hydrogen, deuterium, a halogen, a cyano, 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 tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubsti
  • Ar 1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
  • R 31 to R 33 each independently, represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, 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;
  • o and p each independently, represent an integer of 0 to 4; where o or p is an integer of 2 or more, each of R 21 or R 22 may be the same or different;
  • q and r each independently, represent an integer of 0 to 3; where q or r is an integer of 2 or more, each of R 23 or R 24 may be the same or different; and
  • the combination of a dopant compound and a host compound of the present disclosure can provide an organic electroluminescent device showing long lifespan, excellent luminous and power efficiencies, and a low driving voltage.
  • the present disclosure relates to a combination of one or more dopant compounds represented by formula 1 and one or more host compounds represented by formula 2, and an organic electroluminescent device comprising the same.
  • the dopant compound represented by formula 1 will be described in detail.
  • the one or more dopant compounds represented by formula 1 is one or more of the compounds represented by the following formulae 3 to 5:
  • R 1 to R 6 , a to f, X, L 2 , and L 3 are as defined in formula 1 above.
  • L 2 and L 3 each independently, may represent the structure selected from A-1, A-4, and A-5. More preferably, both L 2 and L 3 may have the same structure which is selected from A-1, A-4, and A-5; or one of L 2 and L 3 may have the structure A-1, and the other may have the structure A-4 or A-5.
  • L 2 and L 3 each independently, may be selected from A-2, A-4, and A-5. More preferably, both L 2 and L 3 may have the same structure which is selected from A-2, A-4, and A-5; or one of L 2 and L 3 may have the structure A-2, and the other may have the structure A-4 or A-5.
  • L 2 and L 3 each independently, may be selected from A-3, A-4, and A-5. More preferably, both L 2 and L 3 may have the same structure which is selected from A-3, A-4, and A-5; or one of L 2 and L 3 may have the structure A-3, and the other may have the structure A-4 or A-5.
  • the dopant compound represented by formula 1 may be represented by formula 3.
  • R 1 to R 11 each independently, may represent hydrogen, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C3-C10)cycloalkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl.
  • R 1 to R 8 each independently, may represent hydrogen, (C1-C10)alkyl, (C3-C10)cycloalkyl, (C6-C18)aryl, or a (6- to 18-membered)heteroaryl; and R 9 to R 11 , each independently, may represent hydrogen or a (C1-C10)alkyl.
  • a to h each independently, are an integer of 0 to 2.
  • the compound of formula 3 includes the following, but is not limited thereto:
  • the compound of formula 4 includes the following, but is not limited thereto:
  • the compound of formula 5 includes the following, but is not limited thereto:
  • the compounds of formula 1 including the compounds of formulae 3 to 5 can be prepared by a synthetic method known to one skilled in the art. For example, they can be prepared according to the methods disclosed in Korean Patent Application Laying-Open No. 10-2011-0130476.
  • the host compound represented by formula 2 will be described in detail.
  • the one or more host compounds represented by formula 2 may be one or more of the compounds represented by the following formulae 6 to 12:
  • R 21 to R 24 , Y 1 , L 4 , L 5 , Ar 1 , o, p, q, and r are as defined above.
  • the one or more host compounds represented by formula 2 may be one or more of the compounds represented by formulae 6, 9, and 10.
  • L 4 and L 5 each independently, may represent, preferably, a single bond, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl; and more preferably, a single bond, or a substituted or unsubstituted (C6-C18)aryl.
  • L 4 and L 5 each independently, may represent a single bond, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl.
  • R 21 to R 24 each independently, may represent, preferably, hydrogen, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl; 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.
  • Y 1 may represent preferably, O, S or -NR 31 .
  • R 31 may represent preferably, a substituted or unsubstituted (C1-C10)alkyl, or a substituted or unsubstituted (C6-C20)aryl; and more preferably, a substituted or unsubstituted (C6-C18)aryl.
  • R 31 may represent a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted phenylnaphthyl, or a substituted or unsubstituted naphthylphenyl.
  • Ar 1 may represent preferably, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl containing one(1) to three(3) nitrogens as the hetero atom.
  • the substituents of the substituted aryl and the substituted heteroaryl of Ar 1 may be one or more selected from the group consisting of a (C6-C20)aryl unsubstituted or substituted with a halogen or a (C1-C10)alkyl, a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C1-C10)alkyl, a tri(C6-C20)arylsilyl, a di(C1-C10)alkyl(C6-C20)arylsilyl, a (C1-C10)alkyldi(C6-C20)arylsilyl, a mono- or di-(C6-C20)arylamino, and a (C1-C10)alkyl(C6-C20)arylamino.
  • Ar 1 may be selected from the following structures B-1 to B-7:
  • A represents at least one selected from the group consisting of deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a (C1-C30)alkoxy, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a (C3-C30)cycloalkyl, a (5- to 7-membered)heterocycloalkyl, a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, a (C2-C30)alkenyl, a (C2-C30)alkynyl,
  • A may represent at least one selected from the group consisting of a (C6-C20)aryl unsubstituted or substituted with a halogen, a (C1-C10) alkyl, or a (6- to 13-membered)heteroaryl; a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C1-C10)alkyl, or a (C6-C13)aryl unsubstituted or substituted with a (C1-C10)alkyl; a tri(C6-C20)arylsilyl; a di(C1-C10)alkyl(C6-C20)arylsilyl; a (C1-C10)alkyldi(C6-C20)arylsilyl; a mono- or di-(C6-C20)arylamino; and a (C1-C10)alkyl(C6-C20)arylamino
  • the compounds of formulae 6 to 12 include the following, but are not limited thereto:
  • the compounds of formula 2 including the compounds of formulae 6 to 12 can be prepared by a synthetic method known to one skilled in the art. For example, they can be prepared according to the methods disclosed in Korean Patent Application Laying-Open No. 10-2011-0015836.
  • (C1-C30)alkyl indicates a linear or branched alkyl(ene) 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.
  • (C6-C30)aryl indicates a monocyclic or fused ring radical derived from an aromatic hydrocarbon and having 6 to 30, preferably 6 to 20, and more preferably 6 to 18 ring backbone carbon atoms, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, indanyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.
  • “Substituted” in the expression, “substituted or unsubstituted,” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e. a substituent.
  • the substituents of the substituted (C1-C30)alkyl, the substituted (C3-C30)cycloalkyl, the substituted (C6-C30)aryl, the substituted (5- to 30-membered)heteroaryl, the substituted silyl and the substituted amino of R 1 to R 7 , R 21 to R 24 , R 31 to R 33 , L 1 , L 2 , and Ar 1 of formulae 1 and 2, 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 unsubstit
  • the organic electroluminescent device comprising the combination of the dopant compound of formula 1 and the host compound of formula 2 will be described in detail.
  • 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.
  • One of the first and second electrodes may be an anode and the other may be a cathode.
  • the organic layer may comprise a light-emitting layer, and the light-emitting layer may comprise the combination of one or more dopant compounds represented by formula 1 and one or more host compounds represented by formula 2.
  • the light-emitting layer may be a single layer or a multiple layer in which two or more layers are laminated.
  • a doping amount of the dopant compound is less than 20 wt%, preferably less than 17 wt% based on the total amount of the host compound and the dopant compound, in view of color purity, luminous efficiency, power efficiency, and a driving voltage.
  • the light-emitting layer may further comprise one or more materials, for example, an additional second host material, other than the combination of the compound of formula 1 and the compound of formula 2.
  • the organic layer may further comprise one or more layers selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, and a hole blocking layer.
  • the present disclosure provides a material for preparing an organic electroluminescent device, and an organic electroluminescent device comprising the material.
  • the material may comprise one or more dopant compounds of formula 1 to be combined with one or more host compounds of formula 2.
  • the material may comprise one or more host compounds of formula 2 to be combined with one or more dopant compounds of formula 1.
  • the material may further comprise a conventional compound(s) which has been comprised for preparing an organic electroluminescent device.
  • the material may be a composition or a mixture.
  • the present disclosure provides an organic layer comprising one or more dopant compounds of formula 1 and one or more host compounds of formula 2.
  • the organic layer may comprise two or more layers, wherein the dopant compound and the host compound may be comprised in a layer at the same time, or they may be comprised in two different layers, respectively.
  • the present disclosure provides an organic electroluminescent device comprising the organic layer.
  • the organic electroluminescent device of the present disclosure 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, in addition to the combination of the present disclosure, 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 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 field, besides the combination of the present disclosure. If necessary, it may further comprise an orange light-emitting layer or a yellow light-emitting layer.
  • at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound known in the field, besides the combination of the present disclosure. If necessary, it may further comprise an orange light-emitting layer or a yellow light-emitting layer.
  • 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.
  • each layer of the organic electroluminescent device of the present disclosure dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as spin coating, dip coating, and flow coating methods can be used.
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as spin coating, dip coating, and flow coating methods can be used.
  • a layer comprising the compound of formula 1 and the compound of formula 2 can be formed by co-evaporation.
  • An OLED was produced using the combination according to the present disclosure.
  • a transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) (Samsung Corning) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and then was 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 -diphenylbenzen-1,4-diamine) was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the introduced material above, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl was then introduced into another cell of the vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, compound H-19 was introduced into one cell of the vacuum vapor depositing apparatus, as a host compound, and compound D-2 was introduced into another cell as a dopant compound.
  • 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.
  • 2-(4-(9,10-di(naphthalen-2-yl) anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole was then introduced into one cell, and lithium quinolate was introduced into another cell.
  • the two materials were evaporated at the same rate, so that they were respectively deposited in a doping amount of 50 wt% to form an electron transport layer having a thickness of 30 nm on the light-emitting layer.
  • an Al cathode having a thickness of 150 nm was then deposited by another vacuum vapor deposition apparatus on the electron injection layer.
  • An OLED was produced. All the material used for producing the OLED were those purified by vacuum sublimation at 10 -6 torr. The produced OLED showed green emission having a luminance of 2,430 cd/m 2 and a power efficiency of 36.6 lm/W at 3.4 V.
  • An OLED was produced in the same manner as in Device Example 1, except for using compound H-49 and compound D-3 as the host compound and the dopant compound for the light-emitting layer.
  • the produced OLED showed green emission having a luminance of 3,440 cd/m 2 and a power efficiency of 43.2 lm/W at 3.0 V.
  • An OLED was produced in the same manner as in Device Example 1, except for using compound H-93 and compound D-2 as the host compound and the dopant compound for the light-emitting layer.
  • the produced OLED showed green emission having a luminance of 1,210 cd/m 2 and a power efficiency of 25.7 lm/W at 3.1 V.
  • An OLED was produced in the same manner as in Device Example 1, except for using compound H-19 and compound D-3 as the host compound and the dopant compound for the light-emitting layer.
  • the produced OLED showed green emission having a luminance of 3,840 cd/m 2 and a power efficiency of 60.6 lm/W at 2.7 V.
  • An OLED was produced in the same manner as in Device Example 1, except for using compound H-49 and compound D-2 as the host compound and the dopant compound for the light-emitting layer.
  • the produced OLED showed green emission having a luminance of 930 cd/m 2 and a power efficiency of 42.3 lm/W at 3.2 V.
  • An OLED was produced in the same manner as in Device Example 1, except for using compound H-19 and compound D-96 as the host compound and the dopant compound for the light-emitting layer.
  • the produced OLED showed green emission having a luminance of 1,210 cd/m 2 and a power efficiency of 55.5 lm/W at 2.6 V.
  • An OLED was produced in the same manner as in Device Example 1, except for using compound H-73 and compound D-3 as the host compound and the dopant compound for the light-emitting layer.
  • the produced OLED showed green emission having a luminance of 2,960 cd/m 2 and a power efficiency of 42.2 lm/W at 2.6 V.
  • An OLED was produced in the same manner as in Device Example 1, except for using compound H-6 and compound D-3 as the host compound and the dopant compound for the light-emitting layer.
  • the produced OLED showed green emission having a luminance of 1,020 cd/m 2 and a power efficiency of 56.5 lm/W at 2.8 V.
  • An OLED was produced in the same manner as in Device Example 1, except that comparative compound 1 shown below and compound D-2 were used as a host compound and a dopant compound to form a light-emitting layer having a thickness of 30 nm on the hole transport layer; and 4-(3-(triphenylen-2-yl)phenyl)dibenzo[b,d]thiophene was deposited to form a hole blocking layer having a thickness of 10 nm.
  • the produced OLED showed green emission having a luminance of 3,000 cd/m 2 and a power efficiency of 16.81 lm/W at 6.9 V.
  • the Device Examples confirm that the combination of the present disclosure provides better luminous characteristics than the conventional materials.
  • the organic electroluminescent device can show excellent luminous characteristics and lowered driving voltage, thereby improving power efficiency to reduce power consumption.

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Abstract

The present disclosure relates to a specific combination of a dopant compound and a host compound, and an organic electroluminescent device comprising the combination. By comprising the combination of the present disclosure, the organic electroluminescent device showing excellence in luminous efficiency, power efficiency, and color purity, low driving voltage, and good lifespan can be provided.

Description

COMBINATION OF A HOST COMPOUND AND A DOPANT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
The present disclosure relates to a combination of a host compound and a dopant 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].
Generally, an organic EL device has a structure comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer of the organic EL device comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. When a voltage is applied to the organic EL device, holes and electrons are injected from an anode and a cathode, respectively, to the light-emitting layer. Excitons having high energy are formed by recombinations between the holes and the electrons, the energy puts the light-emitting organic compound in an excited state, and the decay of the excited state results in a relaxation of the energy level into a ground state, accompanied by light-emission.
The most important factor determining luminous efficiency in the organic EL device is light-emitting materials. The light-emitting material needs to have high quantum efficiency, high electron mobility, and high hole mobility. Furthermore, the light-emitting layer formed by the light-emitting material needs to be uniform and stable. Depending on colors visualized by light-emission, the light-emitting materials can be classified as a blue-, green-, or red-emitting material, and a yellow- or orange-emitting material can be additionally included therein. Depending on its function, the light-emitting materials can be classified as a host material and a dopant material. It is known that devices showing the best electroluminescent characteristics comprise a light-emitting layer in which a dopant is doped into a host, in general. Furthermore, depending on the excited state, the light-emitting material can be classified as fluorescent materials (singlet state) and phosphorescent materials (triplet state). Fluorescent materials have been widely used for the organic EL device. However, since phosphorescent materials enhance luminous efficiency for converting electricity to light by four (4) times compared to fluorescent materials and can reduce power consumption to have longer lifespan, development of phosphorescent light-emitting materials are widely being researched.
Recently, the development of an organic EL device providing high efficiency and long lifespan is an urgent issue. In particular, considering EL characteristic requirements for a middle or large-sized panel of OLED, materials showing better characteristics than conventional ones must be urgently developed.
Iridium(III) complexes have been widely known as phosphorescent dopant 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.
The host materials influence the efficiency and performance of the EL device, and thus their selection is important. At present, 4,4’-N,N’-dicarbazol-biphenyl (CBP) is the most widely known host material for phosphorescent materials. Recently, Pioneer (Japan) et al., developed a high performance organic EL device using bathocuproine (BCP) and aluminum(III) bis(2-methyl-8-quinolinate)(4-phenylphenolate) (BAlq) etc., as host materials, which were known as hole blocking materials.
Although these phosphorescent host materials provide good light-emitting characteristics, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, their degradation may occur during a high-temperature deposition process in a vacuum. (2) The power efficiency of the organic EL device is given by [(π/voltage) × current efficiency], and the power efficiency is inversely proportional to the voltage. Although the organic EL device comprising phosphorescent host materials provides higher current efficiency (cd/A) than one comprising fluorescent host materials, a significantly high driving voltage is necessary. Thus, there is no merit in terms of power efficiency (lm/W). (3) Furthermore, the operational lifespan of the organic EL device is short, and luminous efficiency is still required to be improved.
Korean Patent Application Laying-open No. 10-2011-0130475 discloses iridium complexes for being used as a dopant compound of an organic electroluminescent device, and compounds having triphenylene moiety and dibenzothiophene moiety as a host compound suitable for being combined with the iridium complexes. Korean Patent Application Laying-open No. 10-2011-0015836 discloses organic electroluminescent compounds having a carbazole moiety, and a combination of said compound and Ir(ppy)3 or (piq)2Ir(acac) [bis-(1-phenylisoquinolyl)iridium(III) acetylacetonate]. However, where the conventional combination of a dopant compound and a host compound is applied to an organic electroluminescent device, the characteristics such as a driving voltage, luminous efficiency, and power efficiency are not satisfactory.
The present inventors found that when using a combination of a specific iridium complex and a specific carbazole-containing compound as a light-emitting material, it is possible to produce an organic electroluminescent device showing excellence in luminous and power efficiencies at a low driving voltage.
The objective of the present disclosure is to provide a combination of a dopant compound and a host compound, which can provide excellent luminous and power efficiencies, long lifespan, and a lowered driving voltage; and an organic electroluminescent device showing long lifespan, excellent luminous and power efficiencies, and a low driving voltage by comprising the combination.
The present inventors found that the above objective can be achieved by a combination of one or more dopant compounds represented by the following formula 1 and one or more host compounds represented by the following formula 2, and an organic electroluminescent device comprising the same.
Figure PCTKR2014009734-appb-I000001
wherein L1 to L3, each independently, are selected from the following structures A-1 to A-5, with the proviso that at least one of L1 to L3 is represented by A-1, A-2 or A-3:
Figure PCTKR2014009734-appb-I000002
X represents O or S;
R1 to R11, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; and
a to h, each independently, represent an integer of 0 to 4; where a, b, c, d, e, f, g, or h is an integer of 2 or more, each of R1, R2, R3, R4, R5, R6, R7, or R8 may be the same or different,
Figure PCTKR2014009734-appb-I000003
wherein Y1 represents O, S, -NR31 or -CR32R33;
L4 and L5, each independently, represent a single bond, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
R21 to R24, each independently, represent hydrogen, deuterium, a halogen, a cyano, 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 tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, 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;
Ar1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
R31 to R33, each independently, represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, 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;
o and p, each independently, represent an integer of 0 to 4; where o or p is an integer of 2 or more, each of R21 or R22 may be the same or different;
q and r, each independently, represent an integer of 0 to 3; where q or r is an integer of 2 or more, each of R23 or R24 may be the same or different; and
the heteroaryl contains at least one hetero atom selected from B, N, O, S, P(=O), Si, and P.
The combination of a dopant compound and a host compound of the present disclosure, can provide an organic electroluminescent device showing long lifespan, excellent luminous and power efficiencies, and a low driving voltage.
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the invention, and is not meant in any way to restrict the scope of the invention.
The present disclosure relates to a combination of one or more dopant compounds represented by formula 1 and one or more host compounds represented by formula 2, and an organic electroluminescent device comprising the same.
The dopant compound represented by formula 1 will be described in detail.
The one or more dopant compounds represented by formula 1 is one or more of the compounds represented by the following formulae 3 to 5:
Figure PCTKR2014009734-appb-I000004
wherein, R1 to R6, a to f, X, L2, and L3 are as defined in formula 1 above.
In formula 3, preferably, L2 and L3, each independently, may represent the structure selected from A-1, A-4, and A-5. More preferably, both L2 and L3 may have the same structure which is selected from A-1, A-4, and A-5; or one of L2 and L3 may have the structure A-1, and the other may have the structure A-4 or A-5.
In formula 4, preferably, L2 and L3, each independently, may be selected from A-2, A-4, and A-5. More preferably, both L2 and L3 may have the same structure which is selected from A-2, A-4, and A-5; or one of L2 and L3 may have the structure A-2, and the other may have the structure A-4 or A-5.
In formula 5, preferably, L2 and L3, each independently, may be selected from A-3, A-4, and A-5. More preferably, both L2 and L3 may have the same structure which is selected from A-3, A-4, and A-5; or one of L2 and L3 may have the structure A-3, and the other may have the structure A-4 or A-5.
Preferably, the dopant compound represented by formula 1 may be represented by formula 3.
In formulae 1 and 3 to 5, preferably, R1 to R11, each independently, may represent hydrogen, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C3-C10)cycloalkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl. More preferably, R1 to R8, each independently, may represent hydrogen, (C1-C10)alkyl, (C3-C10)cycloalkyl, (C6-C18)aryl, or a (6- to 18-membered)heteroaryl; and R9 to R11, each independently, may represent hydrogen or a (C1-C10)alkyl. Preferably, a to h, each independently, are an integer of 0 to 2.
More specifically, the compound of formula 3 includes the following, but is not limited thereto:
Figure PCTKR2014009734-appb-I000005
Figure PCTKR2014009734-appb-I000006
Figure PCTKR2014009734-appb-I000007
Figure PCTKR2014009734-appb-I000008
Figure PCTKR2014009734-appb-I000009
Figure PCTKR2014009734-appb-I000010
Figure PCTKR2014009734-appb-I000011
Figure PCTKR2014009734-appb-I000012
Figure PCTKR2014009734-appb-I000013
Figure PCTKR2014009734-appb-I000014
Figure PCTKR2014009734-appb-I000015
Figure PCTKR2014009734-appb-I000016
Figure PCTKR2014009734-appb-I000017
Figure PCTKR2014009734-appb-I000018
Figure PCTKR2014009734-appb-I000019
Figure PCTKR2014009734-appb-I000020
Figure PCTKR2014009734-appb-I000021
Figure PCTKR2014009734-appb-I000022
Figure PCTKR2014009734-appb-I000023
Figure PCTKR2014009734-appb-I000024
More specifically, the compound of formula 4 includes the following, but is not limited thereto:
Figure PCTKR2014009734-appb-I000025
Figure PCTKR2014009734-appb-I000026
Figure PCTKR2014009734-appb-I000027
Figure PCTKR2014009734-appb-I000028
Figure PCTKR2014009734-appb-I000029
Figure PCTKR2014009734-appb-I000030
Figure PCTKR2014009734-appb-I000031
Figure PCTKR2014009734-appb-I000032
More specifically, the compound of formula 5 includes the following, but is not limited thereto:
Figure PCTKR2014009734-appb-I000033
Figure PCTKR2014009734-appb-I000034
Figure PCTKR2014009734-appb-I000035
Figure PCTKR2014009734-appb-I000036
Figure PCTKR2014009734-appb-I000037
Figure PCTKR2014009734-appb-I000038
The compounds of formula 1 including the compounds of formulae 3 to 5 can be prepared by a synthetic method known to one skilled in the art. For example, they can be prepared according to the methods disclosed in Korean Patent Application Laying-Open No. 10-2011-0130476.
The host compound represented by formula 2 will be described in detail.
The one or more host compounds represented by formula 2 may be one or more of the compounds represented by the following formulae 6 to 12:
Figure PCTKR2014009734-appb-I000039
Figure PCTKR2014009734-appb-I000040
Figure PCTKR2014009734-appb-I000041
Figure PCTKR2014009734-appb-I000042
wherein, R21 to R24, Y1, L4, L5, Ar1, o, p, q, and r are as defined above.
Preferably, the one or more host compounds represented by formula 2 may be one or more of the compounds represented by formulae 6, 9, and 10.
In formulae 2 or 6 to 12, L4 and L5, each independently, may represent, preferably, a single bond, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl; and more preferably, a single bond, or a substituted or unsubstituted (C6-C18)aryl. Specifically, L4 and L5, each independently, may represent a single bond, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl.
R21 to R24, each independently, may represent, preferably, hydrogen, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl; 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.
Y1 may represent preferably, O, S or -NR31. R31 may represent preferably, a substituted or unsubstituted (C1-C10)alkyl, or a substituted or unsubstituted (C6-C20)aryl; and more preferably, a substituted or unsubstituted (C6-C18)aryl. Specifically, R31 may represent a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted phenylnaphthyl, or a substituted or unsubstituted naphthylphenyl.
Ar1 may represent preferably, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl containing one(1) to three(3) nitrogens as the hetero atom. The substituents of the substituted aryl and the substituted heteroaryl of Ar1, each independently, may be one or more selected from the group consisting of a (C6-C20)aryl unsubstituted or substituted with a halogen or a (C1-C10)alkyl, a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C1-C10)alkyl, a tri(C6-C20)arylsilyl, a di(C1-C10)alkyl(C6-C20)arylsilyl, a (C1-C10)alkyldi(C6-C20)arylsilyl, a mono- or di-(C6-C20)arylamino, and a (C1-C10)alkyl(C6-C20)arylamino.
Preferably, Ar1 may be selected from the following structures B-1 to B-7:
Figure PCTKR2014009734-appb-I000043
wherein, A represents at least one selected from the group consisting of deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a (C1-C30)alkoxy, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a (C3-C30)cycloalkyl, a (5- to 7-membered)heterocycloalkyl, a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, a (C2-C30)alkenyl, a (C2-C30)alkynyl, a cyano, a mono- or di-(C1-C30)alkylamino, a mono- or di-(C6-C30)arylamino, a (C1-C30)alkyl(C6-C30)arylamino, a di(C6-C30)arylboronyl, a di(C1-C30)alkylboronyl, a (C1-C30)alkyl(C6-C30)arylboronyl, a (C6-C30)aryl(C1-C30)alkyl, a carboxy, a nitro, and a hydroxy; m represents an integer of 0 to 4; where m is 2 or more, each of A may be the same or different; and * represents a bonding site. Preferably, A may represent at least one selected from the group consisting of a (C6-C20)aryl unsubstituted or substituted with a halogen, a (C1-C10) alkyl, or a (6- to 13-membered)heteroaryl; a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C1-C10)alkyl, or a (C6-C13)aryl unsubstituted or substituted with a (C1-C10)alkyl; a tri(C6-C20)arylsilyl; a di(C1-C10)alkyl(C6-C20)arylsilyl; a (C1-C10)alkyldi(C6-C20)arylsilyl; a mono- or di-(C6-C20)arylamino; and a (C1-C10)alkyl(C6-C20)arylamino. Preferably, m may represent an integer of 0 to 2; or may represent 0 or 1.
More specifically, the compounds of formulae 6 to 12 include the following, but are not limited thereto:
Figure PCTKR2014009734-appb-I000044
Figure PCTKR2014009734-appb-I000045
Figure PCTKR2014009734-appb-I000046
Figure PCTKR2014009734-appb-I000047
Figure PCTKR2014009734-appb-I000048
Figure PCTKR2014009734-appb-I000049
Figure PCTKR2014009734-appb-I000050
Figure PCTKR2014009734-appb-I000051
Figure PCTKR2014009734-appb-I000052
Figure PCTKR2014009734-appb-I000053
Figure PCTKR2014009734-appb-I000054
Figure PCTKR2014009734-appb-I000055
Figure PCTKR2014009734-appb-I000056
Figure PCTKR2014009734-appb-I000057
Figure PCTKR2014009734-appb-I000058
Figure PCTKR2014009734-appb-I000059
Figure PCTKR2014009734-appb-I000060
Figure PCTKR2014009734-appb-I000061
Figure PCTKR2014009734-appb-I000062
Figure PCTKR2014009734-appb-I000063
The compounds of formula 2 including the compounds of formulae 6 to 12 can be prepared by a synthetic method known to one skilled in the art. For example, they can be prepared according to the methods disclosed in Korean Patent Application Laying-Open No. 10-2011-0015836.
Herein, “(C1-C30)alkyl” indicates a linear or branched alkyl(ene) 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. “(5- to 7-membered) heterocycloalkyl” indicates a cycloalkyl having 5 to 7 ring backbone atoms including at least one hetero atom selected from B, N, O, S, P(=O), Si, and P, preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. “(C6-C30)aryl” indicates a monocyclic or fused ring radical derived from an aromatic hydrocarbon and having 6 to 30, preferably 6 to 20, and more preferably 6 to 18 ring backbone carbon atoms, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, indanyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc. “(5- to 30-membered) heteroaryl” indicates an aryl 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, hetero atom selected from the group consisting of B, N, O, S, P(=O), Si, and P; may be 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, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, etc. “Halogen” includes F, Cl, Br, and I.
“Substituted” in the expression, “substituted or unsubstituted,” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e. a substituent. The substituents of the substituted (C1-C30)alkyl, the substituted (C3-C30)cycloalkyl, the substituted (C6-C30)aryl, the substituted (5- to 30-membered)heteroaryl, the substituted silyl and the substituted amino of R1 to R7, R21 to R24, R31 to R33, L1, L2, and Ar1 of formulae 1 and 2, 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 unsubstituted or substituted with a (C1-C30)alkyl, a (5- to 30-membered)heteroaryl unsubstituted or substituted with a (C1-C30)alkyl, a (C3-C30)cycloalkyl, a (5- to 7-membered)heterocycloalkyl, a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, a (C2-C30)alkenyl, a (C2-C30)alkynyl, a cyano, a mono- or di-(C1-C30)alkylamino, a mono- or di-(C6-C30)arylamino, a (C1-C30)alkyl(C6-C30)arylamino, a di(C6-C30)arylboronyl, a di(C1-C30)alkylboronyl, a (C1-C30)alkyl(C6-C30)arylboronyl, a (C6-C30)aryl(C1-C30)alkyl, a carboxy, a nitro, and a hydroxy.
The organic electroluminescent device comprising the combination of the dopant compound of formula 1 and the host compound of formula 2 will be described in detail.
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. One of the first and second electrodes may be an anode and the other may be a cathode.
The organic layer may comprise a light-emitting layer, and the light-emitting layer may comprise the combination of one or more dopant compounds represented by formula 1 and one or more host compounds represented by formula 2. The light-emitting layer may be a single layer or a multiple layer in which two or more layers are laminated. Regarding the combination ratio between the dopant compound and the host compound in the light-emitting layer, it is preferable that a doping amount of the dopant compound is less than 20 wt%, preferably less than 17 wt% based on the total amount of the host compound and the dopant compound, in view of color purity, luminous efficiency, power efficiency, and a driving voltage. The light-emitting layer may further comprise one or more materials, for example, an additional second host material, other than the combination of the compound of formula 1 and the compound of formula 2. The organic layer may further comprise one or more layers selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, and a hole blocking layer.
According to another aspect of the present disclosure, the present disclosure provides a material for preparing an organic electroluminescent device, and an organic electroluminescent device comprising the material. The material may comprise one or more dopant compounds of formula 1 to be combined with one or more host compounds of formula 2. The material may comprise one or more host compounds of formula 2 to be combined with one or more dopant compounds of formula 1. The material may further comprise a conventional compound(s) which has been comprised for preparing an organic electroluminescent device. The material may be a composition or a mixture.
According to another aspect of the present disclosure, the present disclosure provides an organic layer comprising one or more dopant compounds of formula 1 and one or more host compounds of formula 2. The organic layer may comprise two or more layers, wherein the dopant compound and the host compound may be comprised in a layer at the same time, or they may be comprised in two different layers, respectively. The present disclosure provides an organic electroluminescent device comprising the organic layer.
The organic electroluminescent device of the present disclosure 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, in addition to the combination of the present disclosure, 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.
In addition, 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 field, besides the combination of the present disclosure. If necessary, it may further comprise an orange light-emitting layer or a yellow light-emitting layer.
In the organic electroluminescent device of the present disclosure, preferably, 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.
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 and ion plating methods, or wet film-forming methods such as spin coating, dip coating, and flow coating methods can be used. For example, a layer comprising the compound of formula 1 and the compound of formula 2 can be formed by co-evaporation.
Hereinafter, the 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.
Example 1: Preparation of compound D-2
Figure PCTKR2014009734-appb-I000064
Figure PCTKR2014009734-appb-I000065
Figure PCTKR2014009734-appb-I000066
Preparation of compound 1-1
After mixing 2-phenylpyridine (10g, 32mmol), iridium(III) chloride hydrate (IrCl3 ·xH2O) (8.1g, 29mmol), 2-ethoxy ethanol (220mL) and H2O (74mL), the mixture was stirred at 140°C for 24 hours. After the reaction, the mixture was cooled to room temperature, washed with water and methanol (MeOH), and then dried to obtain compound 1-1 (11g, 71%).
Preparation of compound 1-2
After dissolving compound 1-1 (10g, 9 mmol) in methylene chloride (MC) 4L, silver trifluoromethane sulfate (AgOTf) (5g, 19mmol) dissolved in methanol (MeOH) (400 mL) was added slowly thereto. The mixture was stirred for 12 hours at room temperature. After the reaction, the reaction mixture was filtered. The filtrate was dried to obtain compound 1-2 (12g, 94%).
Preparation of compound 1-3
After mixing 2-bromopyridine (10g, 63mmol), dibenzo[b,d]furan-4-yl boronic acid (16g, 76mmol), palladium(0) tetrakis(triphenylphosphine) [Pd(PPh3)4] (2.2g, 2mmol), Na2CO3 (20g, 19mmol), toluene (300mL), ethanol (EtOH) (150 mL) and H2O (10mL), the mixture was stirred at 100°C for 2 hours. After the reaction, the mixture was cooled to room temperature, extracted with ethyl acetate (EA), dried with MgSO4, and then distilled under reduced pressure. The resultant was subjected to column chromatography with methylene chloride (MC) / hexane (Hx) = 1/3 to obtain compound 1-3 (10g, 63%, white solid).
Preparation of compound D-2
After adding compound 1-3 (7g, 28mmol) and compound 1-2 (10g, 14mmol) to MeOH (200mL), the mixture was stirred under reflux for 12 hours. After the reaction, the mixture was cooled to room temperature, filtered, and then, subjected to column chromatography with chloroform (CHCl3) to obtain compound D-2 (2g, 17%).
Melting Point (mp) 400℃ or more, UV 292nm, PL 525nm, LC 99.06%
Example 2: Preparation of compound D-3
Figure PCTKR2014009734-appb-I000067
Figure PCTKR2014009734-appb-I000068
Preparation of compound 2-1
After mixing 2-bromo-5-methylpyridine (15g, 87mmol), phenylboronic acid (14g, 114mmol), Pd(PPh3)4 (3g, 2.6mmol), Na2CO3 (36g, 260mmol), toluene (300mL), EtOH (150mL) and H2O (130mL), the mixture was stirred at 100°C for 3 hours. After the reaction, the mixture was extracted with EA, dried with MgSO4, and distilled under reduced pressure. The resultant was subjected to column chromatography with MC/Hx = 1/2 to obtain compound 2-1 (10g, 68%, white solid).
Preparation of compound 2-2
After mixing compound 2-1 (10g, 30mmol), IrCl3·xH2O (8g, 27mmol), 2-ethoxy ethanol (200mL) and H2O (70mL), the mixture was stirred at 140°C for 24 hours. After the reaction, the mixture was cooled to room temperature, washed with H2O and MeOH, and dried to obtain compound 2-2 (11g, 75%).
Preparation of compound 2-3
After dissolving compound 2-2 (11g, 10mmol) in MC 4L, AgOTf (5g, 20mmol) dissolved in MeOH (400mL) was added slowly thereto. The mixture was stirred at room temperature for 12 hours. After the reaction, the mixture was filtered. The filtrate was dried to obtain compound 2-3 (13g, 89%).
Preparation of compound D-3
After adding compound 1-3 (7g, 28mmol) and compound 2-3 (10g, 14mmol) to MeOH (200mL), the mixture was stirred under reflux for 12 hours. After the reaction, the mixture was cooled to room temperature, filtered, and subjected to column chromatography with CHCl3 to obtain compound D-3 (3.5g, 33%).
mp 400℃ or more, UV 292nm, PL 527nm, LC 99.19%
Example 3: Preparation of compound D-95
Figure PCTKR2014009734-appb-I000069
Preparation of compound 3-1
After mixing 2-bromo-4-methylpyridine (10g, 63mmol), dibenzo[b,d]furan-4-yl boronic acid (15g, 76mmol), palladium(0) tetrakis(triphenylphosphine) [Pd(PPh3)4] (2.2g, 2mmol), Na2CO3 (20g, 19mmol), toluene (300mL), ethanol (EtOH) (150mL) and H2O (10mL), the mixture was stirred at 100°C for 2 hours. After the reaction, the mixture was cooled to room temperature, extracted with ethyl acetate (EA), dried with MgSO4, and then distilled under reduced pressure. The resultant was subjected to column chromatography with MC/Hx = 1/3 to obtain compound 3-1 (11g, 67%, white solid).
Preparation of compound D-95
After adding compound 3-1 (7g, 28mmol) and compound 2-3 (10g, 14mmol) to MeOH (200mL), the mixture was stirred under reflux for 12 hours. After the reaction, the mixture was cooled to room temperature, filtered, and subjected to column chromatography with chloroform (CHCl3) to obtain compound D-95 (1.5g, 15%).
mp 400℃ or more, UV 292nm, PL 519nm, LC 99.12%
Example 4: Preparation of compound D-96
Figure PCTKR2014009734-appb-I000070
Preparation of compound 4-1
After mixing 2-bromo-5-methylpyridine (10g, 63mmol), dibenzo[b,d]furan-4-yl boronic acid (15g, 76mmol), palladium(0) tetrakis(triphenylphosphine) [Pd(PPh3)4] (2.2g, 2mmol), Na2CO3 (20g, 19mmol), toluene (300mL), ethanol (EtOH) (150mL) and H2O (10mL), the mixture was stirred at 100°C for 2 hours. After the reaction, the mixture was cooled to room temperature, extracted with ethyl acetate (EA), dried with MgSO4, and distilled under reduced pressure. The resultant was subjected to column chromatography with MC/Hx = 1/3 to obtain compound 4-1 (13g, 80%, white solid).
Preparation of compound D-96
After adding compound 4-1 (7g, 28mmol) and compound 2-3 (10g, 14mmol) to MeOH (200mL), the mixture was stirred under reflux for 12 hours. After the reaction, the mixture was cooled to room temperature, filtered, and subjected to column chromatography with chloroform (CHCl3) to obtain compound D-96 (3.0g, 30%).
mp 390℃, UV 290nm, PL 521nm, LC 96.31%
Example 5: Preparation of compound H-1
Figure PCTKR2014009734-appb-I000071
After dissolving 9-phenyl-9H,9'H-3,3'-bicarbazole (10g, 22.4mmol) in dimethylformamide (DMF) (150mL) in a flask, NaH (1.3g, 33.6mmol) was added thereto. After 30 minutes, 2-chloro-4,6-diphenyl-1,3,5-triazine (5g, 18.6mmol) was added to the mixture. The mixture was stirred at room temperature for 4 hours, and methanol was added thereto. The obtained solids were filtered under reduced pressure, and then subjected to column chromatography to obtain compound H-1 (6.5g, 54%).
Example 6: Preparation of compound H-19
Figure PCTKR2014009734-appb-I000072
After introducing 9-phenyl-9H,9'H-3,3'-bicarbazole (36.2g, 93.2mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (40g, 97.9mmol), Pd(OAc)2 (1.25g, 5.59mmol), 2-dicyclohexylphosphino-2'-6'-dimethoxybiphenyl(S-Phos) (4.6g, 11.18mmol), NaO(t-butyl) (26.8g, 279.7mmol) and o-xylene (450mL) into a flask, the mixture was stirred under reflux. After 6 hours, the mixture was cooled to room temperature. The obtained solids were filtered under reduced pressure, and subjected to column chromatography to obtain compound H-19 (34.8g, 52.1%).
Example 7: Preparation of compound H-25
Figure PCTKR2014009734-appb-I000073
Compound H-25 (9.5g, 86%) was obtained in the same manner as in the preparation of compound H-1, by using 9'-phenyl-9H,9'H-2,3'-bicarbazole (7g, 17.14mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (5.1g, 18.85mmol).
Data of the prepared host compounds above, and other host compounds which can be prepared in the manner of the Examples above are shown in Table 1 below.
[Table 1]
Figure PCTKR2014009734-appb-I000074
Figure PCTKR2014009734-appb-I000075
Device Example 1: Production of an OLED using the present combination
An OLED was produced using the combination according to the present disclosure. A transparent electrode indium tin oxide (ITO) thin film (15 Ω/sq) on a glass substrate for an organic light-emitting diode (OLED) (Samsung Corning) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol. The ITO substrate was then mounted on a substrate holder of a vacuum vapor depositing apparatus. N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1-(naphthalen-1-yl)-N4,N4-diphenylbenzen-1,4-diamine) was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate the introduced material above, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate. N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl was then introduced into another cell of the vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, compound H-19 was introduced into one cell of the vacuum vapor depositing apparatus, as a host compound, and compound D-2 was introduced into another cell as a dopant compound. 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. 2-(4-(9,10-di(naphthalen-2-yl) anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole was then introduced into one cell, and lithium quinolate was introduced into another cell. The two materials were evaporated at the same rate, so that they were respectively deposited in a doping amount of 50 wt% to form an electron transport layer having a thickness of 30 nm on the light-emitting layer. After depositing lithium quinolate as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 150 nm was then deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED was produced. All the material used for producing the OLED were those purified by vacuum sublimation at 10-6 torr. The produced OLED showed green emission having a luminance of 2,430 cd/m2 and a power efficiency of 36.6 lm/W at 3.4 V.
[Device Example 2] Production of an OLED using the present combination
An OLED was produced in the same manner as in Device Example 1, except for using compound H-49 and compound D-3 as the host compound and the dopant compound for the light-emitting layer. The produced OLED showed green emission having a luminance of 3,440 cd/m2 and a power efficiency of 43.2 lm/W at 3.0 V.
[Device Example 3] Production of an OLED using the present combination
An OLED was produced in the same manner as in Device Example 1, except for using compound H-93 and compound D-2 as the host compound and the dopant compound for the light-emitting layer. The produced OLED showed green emission having a luminance of 1,210 cd/m2 and a power efficiency of 25.7 lm/W at 3.1 V.
[Device Example 4] Production of an OLED using the present combination
An OLED was produced in the same manner as in Device Example 1, except for using compound H-19 and compound D-3 as the host compound and the dopant compound for the light-emitting layer. The produced OLED showed green emission having a luminance of 3,840 cd/m2 and a power efficiency of 60.6 lm/W at 2.7 V.
[Device Example 5] Production of an OLED using the present combination
An OLED was produced in the same manner as in Device Example 1, except for using compound H-49 and compound D-2 as the host compound and the dopant compound for the light-emitting layer. The produced OLED showed green emission having a luminance of 930 cd/m2 and a power efficiency of 42.3 lm/W at 3.2 V.
[Device Example 6] Production of an OLED using the present combination
An OLED was produced in the same manner as in Device Example 1, except for using compound H-19 and compound D-96 as the host compound and the dopant compound for the light-emitting layer. The produced OLED showed green emission having a luminance of 1,210 cd/m2 and a power efficiency of 55.5 lm/W at 2.6 V.
[Device Example 7] Production of an OLED using the present combination
An OLED was produced in the same manner as in Device Example 1, except for using compound H-73 and compound D-3 as the host compound and the dopant compound for the light-emitting layer. The produced OLED showed green emission having a luminance of 2,960 cd/m2 and a power efficiency of 42.2 lm/W at 2.6 V.
[Device Example 8] Production of an OLED using the present combination
An OLED was produced in the same manner as in Device Example 1, except for using compound H-6 and compound D-3 as the host compound and the dopant compound for the light-emitting layer. The produced OLED showed green emission having a luminance of 1,020 cd/m2 and a power efficiency of 56.5 lm/W at 2.8 V.
[Comparative Device Example 1] Production of an OLED using a conventional combination
An OLED was produced in the same manner as in Device Example 1, except that comparative compound 1 shown below and compound D-2 were used as a host compound and a dopant compound to form a light-emitting layer having a thickness of 30 nm on the hole transport layer; and 4-(3-(triphenylen-2-yl)phenyl)dibenzo[b,d]thiophene was deposited to form a hole blocking layer having a thickness of 10 nm. The produced OLED showed green emission having a luminance of 3,000 cd/m2 and a power efficiency of 16.81 lm/W at 6.9 V.
Figure PCTKR2014009734-appb-I000076
The Device Examples confirm that the combination of the present disclosure provides better luminous characteristics than the conventional materials. By using the combination of the present disclosure, the organic electroluminescent device can show excellent luminous characteristics and lowered driving voltage, thereby improving power efficiency to reduce power consumption.

Claims (11)

  1. A combination of one or more dopant compounds represented by the following formula 1, and one or more host compounds represented by the following formula 2:
    Figure PCTKR2014009734-appb-I000077
    wherein
    L1 to L3, each independently, are selected from the following structures A-1 to A-5, with the proviso that at least one of L1 to L3 is represented by A-1, A-2 or A-3:
    Figure PCTKR2014009734-appb-I000078
    X represents O or S;
    R1 to R11, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; and
    a to h, each independently, represent an integer of 0 to 4; where a, b, c, d, e, f, g, or h is an integer of 2 or more, each of R1, R2, R3, R4, R5, R6, R7, or R8 may be the same or different,
    Figure PCTKR2014009734-appb-I000079
    wherein
    Y1 represents O, S, -NR31 or -CR32R33;
    L4 and L5, each independently, represent a single bond, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
    R21 to R24, each independently, represent hydrogen, deuterium, a halogen, a cyano, 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 tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, 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;
    Ar1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
    R31 to R33, each independently, represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, 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;
    o and p, each independently, represent an integer of 0 to 4; where o or p is an integer of 2 or more, each of R21 or R22 may be the same or different;
    q and r, each independently, represent an integer of 0 to 3; where q or r is an integer of 2 or more, each of R23 or R24 may be the same or different; and
    the heteroaryl contains at least one hetero atom selected from B, N, O, S, P(=O), Si, and P.
  2. The combination according to claim 1, wherein, in formulae 1 and 2, the substituents of the substituted (C1-C30)alkyl, the substituted (C3-C30)cycloalkyl, the substituted (C6-C30)aryl, the substituted (5- to 30-membered)heteroaryl, the substituted silyl and the substituted amino in R1 to R11, R21 to R24, R31 to R33, L4, L5, and Ar1, each independently, are at least one selected from the group consisting of deuterium, a halogen, a (C1-C30)alkyl unsubsituted or substituted with a halogen, a (C1-C30)alkoxy, a (C6-C30)aryl unsubstituted or substituted with a (C1-C30)alkyl, a (5- to 30-membered)heteroaryl unsubstituted or substituted with a (C1-C30)alkyl, a (C3-C30)cycloalkyl, a (5- to 7-membered)heterocycloalkyl, a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, a (C2-C30)alkenyl, a (C2-C30)alkynyl, a cyano, a mono- or di-(C1-C30)alkylamino, a mono- or di-(C6-C30)arylamino, a (C1-C30)alkyl(C6-C30)arylamino, a di(C6-C30)arylboronyl, a di(C1-C30)alkylboronyl, a (C1-C30)alkyl(C6-C30)arylboronyl, a (C6-C30)aryl(C1-C30)alkyl, a carboxy, a nitro, and a hydroxy.
  3. The combination according to claim 1, wherein the one or more dopant compounds represented by formula 1 is one or more of the compounds represented by the following formulae 3 to 5:
    Figure PCTKR2014009734-appb-I000080
    wherein
    R1 to R6, a to f, X, L2, and L3 are as defined in claim 1.
  4. The combination according to claim 1, wherein, R1 to R11, each independently, represent hydrogen, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C3-C10)cycloalkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl.
  5. The combination according to claim 3, wherein the dopant compound represented by formula 3 is selected from the following:
    Figure PCTKR2014009734-appb-I000081
    Figure PCTKR2014009734-appb-I000082
    Figure PCTKR2014009734-appb-I000083
    Figure PCTKR2014009734-appb-I000085
    Figure PCTKR2014009734-appb-I000086
    Figure PCTKR2014009734-appb-I000087
    Figure PCTKR2014009734-appb-I000088
    Figure PCTKR2014009734-appb-I000089
    Figure PCTKR2014009734-appb-I000090
    Figure PCTKR2014009734-appb-I000091
    Figure PCTKR2014009734-appb-I000092
    Figure PCTKR2014009734-appb-I000093
    Figure PCTKR2014009734-appb-I000094
    Figure PCTKR2014009734-appb-I000095
    Figure PCTKR2014009734-appb-I000096
    Figure PCTKR2014009734-appb-I000097
    Figure PCTKR2014009734-appb-I000098
    Figure PCTKR2014009734-appb-I000099
    Figure PCTKR2014009734-appb-I000100
  6. The combination according to claim 3, wherein the dopant compound represented by formula 4 is selected from the following:
    Figure PCTKR2014009734-appb-I000101
    Figure PCTKR2014009734-appb-I000102
    Figure PCTKR2014009734-appb-I000103
    Figure PCTKR2014009734-appb-I000104
    Figure PCTKR2014009734-appb-I000105
    Figure PCTKR2014009734-appb-I000106
    Figure PCTKR2014009734-appb-I000107
    Figure PCTKR2014009734-appb-I000108
  7. The combination according to claim 3, wherein the dopant compound represented by formula 5 is selected from the following:
    Figure PCTKR2014009734-appb-I000109
    Figure PCTKR2014009734-appb-I000110
    Figure PCTKR2014009734-appb-I000111
    Figure PCTKR2014009734-appb-I000112
    Figure PCTKR2014009734-appb-I000113
    Figure PCTKR2014009734-appb-I000114
  8. The combination according to claim 1, wherein the one or more host compounds represented by formula 2 is one or more of the compounds represented by the following formulae 6 to 12:
    Figure PCTKR2014009734-appb-I000115
    Figure PCTKR2014009734-appb-I000116
    Figure PCTKR2014009734-appb-I000117
    Figure PCTKR2014009734-appb-I000118
    wherein
    R21 to R24, Y1, L1, L2, Ar1, o, p, q, and r are as defined in claim 1.
  9. The combination according to claim 1, wherein, in formula 2, L4 and L5, each independently, represent a single bond, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl;
    R21 to R24, each independently, represent hydrogen, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted (5- to 20-membered)heteroaryl, 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;
    Y1 represents O, S or -NR31;
    R31 represents a substituted or unsubstituted (C1-C10)alkyl, or a substituted or unsubstituted (C6-C20)aryl;
    Ar1 represents a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl containing 1 to 3 of nitrogen as the hetero atom; and
    the substituents of the substituted aryl and the substituted heteroaryl of Ar1, each independently, are at least one selected from the group consisting of a (C6-C20)aryl unsubstituted or substituted with a halogen or a (C1-C10)alkyl, a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C1-C10)alkyl, a tri(C6-C20)arylsilyl, a di(C1-C10)alkyl(C6-C20)arylsilyl, a (C1-C10)alkyldi(C6-C20)arylsilyl, a mono- or di-(C6-C20)arylamino, and a (C1-C10)alkyl(C6-C20)arylamino.
  10. The combination according to claim 8, wherein the host compounds represented by formulae 6 to 12 are selected from the following:
    Figure PCTKR2014009734-appb-I000119
    Figure PCTKR2014009734-appb-I000120
    Figure PCTKR2014009734-appb-I000121
    Figure PCTKR2014009734-appb-I000122
    Figure PCTKR2014009734-appb-I000123
    Figure PCTKR2014009734-appb-I000124
    Figure PCTKR2014009734-appb-I000125
    Figure PCTKR2014009734-appb-I000126
    Figure PCTKR2014009734-appb-I000127
    Figure PCTKR2014009734-appb-I000128
    Figure PCTKR2014009734-appb-I000129
    Figure PCTKR2014009734-appb-I000130
    Figure PCTKR2014009734-appb-I000131
    Figure PCTKR2014009734-appb-I000132
    Figure PCTKR2014009734-appb-I000133
    Figure PCTKR2014009734-appb-I000134
    Figure PCTKR2014009734-appb-I000135
    Figure PCTKR2014009734-appb-I000136
    Figure PCTKR2014009734-appb-I000137
    Figure PCTKR2014009734-appb-I000138
  11. The organic electroluminescent device comprising the combination according to claim 1.
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