WO2015156587A1 - Multi-component host material and organic electroluminescent device comprising the same - Google Patents

Multi-component host material and organic electroluminescent device comprising the same Download PDF

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WO2015156587A1
WO2015156587A1 PCT/KR2015/003485 KR2015003485W WO2015156587A1 WO 2015156587 A1 WO2015156587 A1 WO 2015156587A1 KR 2015003485 W KR2015003485 W KR 2015003485W WO 2015156587 A1 WO2015156587 A1 WO 2015156587A1
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group
substituted
unsubstituted
host
alkyl
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PCT/KR2015/003485
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French (fr)
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Hee-Choon Ahn
Young-Kwang Kim
Doo-Hyeon Moon
Su-Hyun Lee
Seon-Woo Lee
Chi-Sik Kim
Kyoung-Jin Park
Nam-Kyun Kim
Kyung-Hoon Choi
Jae-Hoon Shim
Young-Jun Cho
Kyung-Joo Lee
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020150042704A external-priority patent/KR101754715B1/en
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to JP2016559431A priority Critical patent/JP6934299B2/en
Priority to EP24199330.2A priority patent/EP4450590A3/en
Priority to US15/301,978 priority patent/US20170117488A1/en
Priority to EP15777273.2A priority patent/EP3129446A4/en
Priority to CN201580017400.6A priority patent/CN106133113A/en
Publication of WO2015156587A1 publication Critical patent/WO2015156587A1/en
Priority to US17/526,112 priority patent/US20220077405A1/en
Priority to US18/416,245 priority patent/US20240206333A1/en

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    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • the present invention relates to a multi-component host material and an organic electroluminescent device comprising the same.
  • An electroluminescent (EL) device is a self-light-emitting device with the advantage of providing a wider viewing angle, a greater contrast ratio, and a faster response time.
  • An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer (see Appl. Phys. Lett. 51, 913, 1987).
  • the organic EL device changes electric energy into light by the injection of a charge into an organic light-emitting material and commonly comprises an anode, a cathode, and an organic layer formed between the two electrodes.
  • the organic layer of the organic EL device may be composed of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), a light-emitting layer (EML) (containing host and dopant materials), an electron buffer layer, a hole blocking layer (HBL), an electron transport layer (ETL), an electron injection layer (EIL), etc.; the materials used in the organic layer can be classified into a hole injection material, a hole transport material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc., depending on functions.
  • the organic EL device In the organic EL device, holes from an anode and electrons from a cathode are injected into a light-emitting layer by the injection of a charge, and an exciton having high energy is produced by the recombination of holes and electrons.
  • the organic light-emitting compound moves into an excited state by the energy and emits light which changes from energy when the organic light-emitting compound returns to the ground state from the excited state.
  • the most important factor determining luminescent efficiency in an organic EL device is the light-emitting material.
  • the light-emitting material is required to have the following features: high quantum efficiency, high movement degree of an electron and a hole, formability of a uniform layer, and stability.
  • the light-emitting material is classified into blue light-emitting materials, green light-emitting materials, and red light-emitting materials according to the light-emitting color, and further includes yellow light-emitting materials or orange light-emitting materials.
  • the light-emitting material is classified into a host material and a dopant material in the functional aspect. Recently, an urgent task is the development of an organic EL device having high efficacy and long operating lifespan.
  • a host material should have high purity and suitable molecular weight in order to be deposited under vacuum. Furthermore, a host material is required to have high glass transition temperature and pyrolysis temperature to guarantee thermal stability, high electrochemical stability to provide long lifespan, easy formability of an amorphous thin film, good adhesion with adjacent layers, and no movement between layers.
  • a mixed system of a dopant/host material can be used as a light-emitting material to improve color purity, luminescent efficiency, and stability.
  • the device having the most excellent EL properties comprises the light-emitting layer, wherein a dopant is doped onto a host. If the dopant/host material system is used, the selection of the host material is important since the host material greatly influences on efficiency and performance of a light-emitting device.
  • WO 2013/168688 A1 Japanese Patent No. 3139321, Korean Patent No. 10-1170666, Korean Patent Application Laying-open No. 10-2012-0013173, and WO 2013/112557 A1 disclose organic EL devices comprising a dopant/host material system.
  • the above literature use one host component having a carbazole-carbazole skeleton or exclude a host having a cabazole skeleton from second and third hosts.
  • an organic EL device using a multi-component host compounds having a specific bicarbazole derivative which contains an aryl group and a specific carbazole derivative which includes a nitrogen-containing heteroaryl group has high efficiency and long lifespan, compared with using one component host compound in a light-emitting layer.
  • the object of the present invention is to provide an organic EL device having high efficiency and long lifespan.
  • an organic electroluminescent device comprising at least one light-emitting layer between an anode and a cathode, wherein the light-emitting layer comprises a host and a phosphorescent dopant; the host consists of multi-component host compounds; at least a first host compound of the multi-component host compounds is represented by the following formula 1 which is a specific bicarbazole derivative containing an aryl group, and a second host compound is represented by the following formula 2 which is a specific carbazole derivative including a nitrogen-containing heteroaryl group:
  • a 1 and A 2 each independently represent a substituted or unsubstituted (C6-C30)aryl 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
  • Ma represents a substituted or unsubstituted nitrogen-containing 5- to 30-membered heteroaryl group
  • La represents a single bond, or a substituted or unsubstituted (C6-C30)arylene group
  • Xa to Xh 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
  • the fused aromatic or heteroaromatic ring is selected from the group consisting of benzene, indole, indene, benzofuran and benzothiophene, which may be further substituted with a (C1-C10)alkyl group or a (C6-C15)aryl group; and
  • the organic EL device having high efficiency and long lifespan is provided and the production of a display device or a lighting device is possible by using the organic EL device.
  • the compound of formula 1 is represented by the following formula 3, 4, 5, or 6:
  • a 1 , A 2 and X 1 to X 16 are as defined in formula 1.
  • a 1 and A 2 each independently represent a substituted or unsubstituted (C6-C30)aryl group; preferably, a substituted or unsubstituted (C6-C18)aryl group; more preferably, a (C6-C18)aryl group which is unsubstituted or substituted with a (C1-C6)alkyl group, a (C6-C12)aryl group, or a tri(C6-C12)arylsilyl group ; and even more preferably, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, or fluoranthenyl.
  • 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
  • the compound of formula 2 is represented by the following formula 7, 8, or 9:
  • V and W each independently represent a single bond, NR 15 , CR 16 R 17 , S, or O, provided that both V and W neither represent a single bond nor represent NR 15 ;
  • a 2 represents a substituted or unsubstituted (C6-C30)aryl group and may be bonded to Xn or Xo;
  • L 3 and L 4 each independently represent a single bond, or a substituted or unsubstituted (C6-C60)arylene group;
  • Xi represents 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, or a
  • Xj to Xz each independently represent hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, -NR 5 R 6 , or -SiR 7 R 8 R 9 ; or are linked between adjacent substituents to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or
  • Ma, La, Xa, Xb, and Xe to Xh are as defined in formula 2;
  • R 5 to R 9 each independently represent hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group; or are linked between adjacent substituents to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring whose carbon atom(s) ring may be replaced with at least one hetero
  • R 16 and R 17 each independently represent hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group; and
  • R 15 represents hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group; preferably, a substituted or unsubstituted (C6-C30)aryl group; and more preferably, a substituted or unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted
  • La represents a single bond, or a substituted or unsubstituted (C6-C30)arylene group; preferably, a single bond, or a substituted or unsubstituted (C6-C12)arylene group; and more preferably, a single bond, a (C6-C12)arylene group which is unsubstituted or substituted with a tri(C6-C10)arylsilyl group or a (C6-C12)aryl group.
  • La represents a single bond, or is represented by one selected from the following formulas 10 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
  • Ma represents a substituted or unsubstituted nitrogen-containing 5- to 11-membered heteroaryl group; preferably, a substituted or unsubstituted nitrogen-containing 6- to 10-membered heteroaryl group; and more preferably, a nitrogen-containing 6- to 10-membered heteroaryl group which is substituted with a substituents(s) selected from the group consisting of an unsubstituted (C6-C18)aryl group, a (C6-C12)aryl group substituted with a cyano group, a (C6-C12)aryl group substituted with a (C1-C6)alkyl group, a (C6-C12)aryl group substituted with a tri(C6-C12)arylsilyl group, and a 6- to 15-membered heteroaryl group.
  • a substituents(s) selected from the group consisting of an unsubstituted (C6-C18)aryl group, a (C6-C12
  • Ma represents a monocyclic-based heteroaryl group selected from the group consisting of pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., or a fused ring-based heteroaryl group selected from the group consisting of benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, naphthyridinyl, quinoxalinyl, carbazolyl, phenanthridinyl, etc.; preferably, triazinyl, pyrimidinyl, pyridyl, quinolyl, isoquinolyl, quinazolin
  • (C1-C30)alkyl(ene) is meant to be a linear or branched alkyl(ene) having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
  • (C2-C30)alkenyl is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • (C2-C30)alkynyl is a linear or branched alkynyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
  • (C3-C30)cycloalkyl is a mono- or polycyclic hydrocarbon having 3 to 30 carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • (C6-C30)aryl(ene) is a monocyclic or fused ring derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, in which the number of carbon atoms is preferably 6 to 20, more preferably 6 to 15, and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.
  • “Nitrogen-containing 5- to 30-membered heteroaryl(ene) group” is an aryl(ene) group having at least one heteroatom N and 5 to 30 ring backbone atoms. 5 to 20 ring backbone atoms and 1 to 4 heteroatom are preferable, and 5 to 15 ring backbone atoms are more preferable.
  • 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.
  • Substituents of the substituted alkyl(ene) group, the substituted alkenyl group, the substituted alkynyl group, the substituted cycloalkyl group, the substituted aryl(ene) group, the substituted heteroaryl(ene) group, the substituted trialkylsilyl group, the substituted triarylsilyl group, the substituted dialkylarylsilyl group, the substituted mono- or di-arylamino group, or the substituted mono- or polycyclic, (C3-C30) 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
  • the substituents are each independently at least one selected from the group consisting of a (C1-C6)alkyl group; a 5- to 15-membered heteroaryl group; a (C6-C18)aryl group which is unsubstituted or substituted with a cyano group or a tri(C6-C12)arylsilyl group; a tri(C6-C12)arylsilyl group; and a (C1-C6)alkyl(C6-C12)aryl group.
  • the compound of formula 1 as a first host compound may be selected from the group consisting of following compounds, but is not limited thereto:
  • the compound of formula 2 as a second host compound may be selected from the group consisting of following compounds, but is not limited thereto:
  • the organic EL device may comprise an anode, a cathode, and at least one organic layer between the two electrodes, wherein the organic layer comprises a light-emitting layer, the light-emitting layer comprises a host and a phosphorescent dopant; the host consists of multi-component host compounds; at least a first host compound of the multi-component host compounds is represented by formula 1 which is a specific bicarbazole derivative containing an aryl group, and a second host compound is represented by formula 2 which is a specific carbazole derivative including a nitrogen-containing heteroaryl group.
  • the light-emitting layer means a layer emitting light and may be a single layer or multi-layers consisting of two or more layers.
  • the doping concentration of dopant compounds to host compounds in the light-emitting layer is preferably less than 20 wt%.
  • the dopants included in the organic EL device of the present invention are preferably one or more phosphorescent dopants.
  • the phosphorescent dopant material applied to the organic electroluminescent device of the present invention is not specifically limited, but preferably may be selected from complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably ortho metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho metallated iridium complex compounds.
  • the phosphorescent dopants may be selected from the group consisting of the compounds represented by the following formulae 101 to 103:
  • L is selected from the following structures:
  • R 100 represents hydrogen, or a substituted or unsubstituted (C1-C30)alkyl 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 halogen(s); a cyano group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group;
  • R 120 to R 123 are linked to an adjacent substituent(s) to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, for example, quinoline;
  • R 124 to R 127 each independently represent hydrogen, deuterium, a halogen, a substitute
  • the phosphorescent dopant material includes the following:
  • the organic EL device of the present invention may further include at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds in the organic layer.
  • the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides, and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
  • a surface layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on an inner surface(s) of one or both electrode(s).
  • a chalcogenide (including oxides) layer of silicon or aluminum is placed on an anode surface of a light-emitting medium layer, and a metal halide layer or metal oxide layer is placed on a cathode surface of an electroluminescent medium layer.
  • the surface layer provides operating 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 their combinations can be used between an anode and a light-emitting layer.
  • the hole injection layer may be multi-layers in order to lower a hole injection barrier (or hole injection voltage) from an anode to a hole transport layer or an electron blocking layer, wherein each of the multi-layers simultaneously uses two compounds.
  • the hole transport layer or the electron blocking layer may also be multi-layers.
  • An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or their combinations can be used between a light-emitting layer and a cathode.
  • the electron buffer layer may be multi-layers in order to control the injection of an electron and improve interface properties between the light-emitting layer and the electron injection layer, wherein each of the multi-layers simultaneously uses two compounds.
  • the hole blocking layer or the electron transport layer may also be multi-layers, wherein each of the multi-layers may use a multi-component of 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 a light-emitting 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 a light-emitting medium.
  • the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • a reductive dopant layer may be employed as a charge-generating layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.
  • each layer constituting the organic electroluminescent device of the present invention dry film-forming methods, such as vacuum deposition, sputtering, plasma, ion plating methods, etc., or wet film-forming methods, such as spin coating, dip coating, flow coating methods, etc., can be used.
  • dry film-forming methods such as vacuum deposition, sputtering, plasma, ion plating methods, etc.
  • wet film-forming methods such as spin coating, dip coating, flow coating methods, etc.
  • co-deposition or mixed-deposition may be used.
  • a thin film is formed by dissolving or dispersing the material constituting each layer in suitable solvents, such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • suitable solvents such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvents are not specifically limited as long as the material constituting each layer is soluble or dispersible in the solvents, which do not cause any problems in forming a layer.
  • a display device or a light device can be produced by using the organic EL device of the present invention.
  • Example 1-1 Production of an OLED device by co-deposition of the first host compound and the second host compound according to the present invention as a host
  • An OLED device comprising the organic electroluminescent compound of the present invention was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and was then stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • ITO indium tin oxide
  • N 4 ,N 4’ -diphenyl-N 4 ,N 4 ’-bis(9-phenyl-9H-carbazole-3-yl)-[1,1’-biphenyl]-4,4’-diamine as HI-1 was introduced into a cell of the vacuum vapor depositing apparatus, and the pressure in the chamber of the apparatus was then controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming a hole injection layer 1 having a thickness of 80 nm on the ITO substrate.
  • 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile as HI-2 was then introduced into another cell of the vacuum vapor depositing apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming a hole injection layer 2 having a thickness of 5 nm on hole injection layer 1.
  • N-([1,1’-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine as HT-1 was introduced into one cell of the vacuum vapor depositing apparatus.
  • compounds H1-1 and H2-2 as hosts were respectively introduced into two cells of the vacuum vapor depositing apparatus and compound D-96 as a dopant was introduced into another cell.
  • the two host materials were evaporated at the same rates of 1:1, and the dopant was evaporated at a different rate and deposited in a doping amount of 3 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 40 nm on the hole transport layer.
  • the produced OLED device showed the driving voltage at a luminance of 1,000nit, luminescent efficiency, CIE color coordinate, and the lifespan taken to be reduced from 100% to 90% of the constant current at a luminance of 5,000nit as provided in Table 1 below.
  • Comparative Example 1-1 Production of an OLED device by using only the second host compound according to the present invention as a host
  • An OLED device was produced in the same manner as in Device Example 1-1, except that only the second host compound was used as a host in a light-emitting layer.
  • the luminescent properties of the OLED devices produced in Device Example 1-1 and Comparative Example 1-1 are provided in Table 1 below.
  • Device Examples 2-1 to 2-13 Production of an OLED device by co -deposition of the first host compound and the second host compound according to the present invention as a host
  • An OLED device was produced in the same manner as in Device Example 1-1, except that hole injection layer 2 has a thickness of 3 nm, hole transport layer 1 has a thickness of 40 nm, hole transport layer 2 is not present, D-25 as a dopant was deposited in a doping amount on 15wt% in a light-emitting layer, the electron transport layer having a thickness of 35 nm was deposited via the evaporation rate of 4:6, the combinations of the first host compound and the second host compound used as hosts in a light-emitting layer are based on Device Examples 2-1 to 2-13 as provided in Table 2 below, and the lifespan taken to be reduced from 100% to 90% of the constant current at a luminance of 15,000nit as provided in Table 2 below.
  • An OLED device was produced in the same manner as in Device Examples 2-1 to 2-13, except that hole injection layer 2 has a thickness of 3 nm, hole transport layer 1 has a thickness of 40 nm, hole transport layer 2 is not present, D-1 as a dopant was used in a light-emitting layer, the electron transport layer having a thickness of 35 nm was deposited via the evaporation rate of 4:6, the combinations of the first host compound and the second host compound used as hosts in a light-emitting layer are based on Device Examples 2-14 to 2-18 as provided in Table 2 below, and the lifespan taken to be reduced from 100% to 90% of the constant current at a luminance of 15,000nit as provided in Table 2 below.
  • Device Examples 3-1 to 3-8 Production of an OLED device by co -deposition of the first host compound and the second host compound according to the present invention as a host
  • An OLED device was produced in the same manner as in Device Examples 2-1 to 2-13, except that hole transport layer 1 has a thickness of 10 nm, hole transport layer 2 of HT-3 has a thickness of 30 nm, D-136 as a dopant was used in a light-emitting layer, and the combinations of the first host compound and the second host compound used as hosts in a light-emitting layer are based on Device Examples 3-1 to 3-8 as provided in Table 2 below.
  • An OLED device was produced in the same manner as in Device Examples 2-1 to 2-13, except that hole transport layer 1 has a thickness of 10 nm, hole transport layer 2 of HT-3 has a thickness of 30 nm, D-164 as a dopant was used in a light-emitting layer, and the combinations of the first host compound and the second host compound used as hosts in a light-emitting layer are based on Device Example 3-9 as provided in Table 2 below.
  • An OLED device was produced in the same manner as in Device Examples 2-1 to 2-13, except that hole transport layer 1 has a thickness of 10 nm, hole transport layer 2 of HT-3 has a thickness of 30 nm, D-168 as a dopant was used in a light-emitting layer, and the combinations of the first host compound and the second host compound used as hosts in a light-emitting layer are based on Device Examples 3-10 to 3-12 as provided in Table 2 below.
  • Example 3-13 Production of an OLED device by co-deposition of the first host compound and the second host compound according to the present invention as a host
  • An OLED device was produced in the same manner as in Device Examples 2-1 to 2-13, except that hole transport layer 1 has a thickness of 10 nm, hole transport layer 2 of HT-3 has a thickness of 30 nm, D-180 as a dopant was used in a light-emitting layer, and the combinations of the first host compound and the second host compound used as hosts in a light-emitting layer are based on Device Example 3-13 as provided in Table 2 below.
  • Comparative Examples 2-1 to 2-3 Production of an OLED device by using only the first host compound according to the present invention as a host
  • An OLED device was produced in the same manner as in Device Examples 2-1 to 2-13, except that the first host compound used as hosts in a light-emitting layer is based on Comparative Examples 2-1 to 2-3 as provided in Table 2 below.
  • Comparative Examples 3-1 to 3-9 Production of an OLED device by using only the second host compound according to the present invention as a host
  • An OLED device was produced in the same manner as in Device Examples 2-1 to 2-13, except that the second host compound used as hosts in a light-emitting layer is based on Comparative Examples 3-1 to 3-9 as provided in Table 2 below.
  • Comparative Example 4-1 Production of an OLED device by using only the second host compound according to the present invention as a hos t
  • An OLED device was produced in the same manner as in Device Examples 3-1 to 3-8, except that the second host compound used as hosts in a light-emitting layer is based on Comparative Example 4-1 as provided in Table 2 below.
  • Device Examples 4-1 to 4-7 Production of an OLED device by co -deposition of the first host compound and the second host compound according to the present invention as a host
  • An OLED device was produced in the same manner as in Device Example 1-1, except that HT-4 was used as a hole transport layer 2, the combinations of the first host compound and the second host compound used as hosts in a light-emitting layer are based on Device Examples 4-1 to 4-7 as provided in Table 3 below, and the lifespan taken to be reduced from 100% to 95% of the constant current at a luminance of 5,000nit as provided in Table 3 below.
  • Comparative Examples 5-1 and 5-2 Production of an OLED device by using only the second host compound according to the present invention as a host
  • An OLED device was produced in the same manner as in Device Examples 4-1 to 4-7, except that the second host compound used as hosts in a light-emitting layer is based on Comparative Examples 5-1 and 5-2 as provided in Table 3 below.
  • Device Examples 5-1 and 5-2 Production of an OLED device by co -deposition of the first host compound and the second host compound according to the present invention as a host
  • An OLED device was produced in the same manner as in Device Examples 3-1 to 3-11, except that D-134 was used as a dopant in a light-emitting layer, the combinations of the first host compound and the second host compound used as hosts in a light-emitting layer are based on Device Examples 5-1 and 5-2 as provided in Table 4 below, and the lifespan taken to be reduced from 100% to 97% of the constant current at a luminance of 15,000nit as provided in Table 4 below.
  • Comparative Examples 6-1 and 6-2 Production of an OLED device by using only the first host compound according to the present invention as a host
  • An OLED device was produced in the same manner as in Device Examples 5-1 and 5-2, except that the first host compound used as hosts in a light-emitting layer is based on Comparative Examples 6-1 and 6-2 as provided in Table 4 below.
  • Comparative Example 7-1 Production of an OLED device by using only the second host compound according to the present invention as a host
  • An OLED device was produced in the same manner as in Device Examples 5-1 and 5-2, except that the second host compound used as hosts in a light-emitting layer is based on Comparative Example 7-1 as provided in Table 4 below.
  • the organic electroluminescent device of the present invention provides longer lifespan compared with conventional devices by comprising a light-emitting layer containing a host and a phosphorescent dopant, wherein the host consists of multi-component host compounds, at least a first host compound of the multi-component host compounds has a specific bicarbazole derivative containing an aryl group, and a second host compound has a specific carbazole derivative including a nitrogen-containing heteroaryl group.

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Abstract

The present invention relates to an organic electroluminescent device comprising at least one light-emitting layer between an anode and a cathode, wherein the light-emitting layer comprises a host and a phosphorescent dopant; the host consists of multi-component host compounds; at least a first host compound of the multi-component host compounds is a specific bicarbazole derivative containing an aryl group, and a second host compound is a specific carbazole derivative including a nitrogen-containing heteroaryl group. According to the present invention, the organic electroluminescent device using the multi-component host compounds has a high efficiency and long lifespan compared with the conventional device using one component host compound.

Description

MULTI-COMPONENT HOST MATERIAL AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
The present invention relates to a multi-component host material and an organic electroluminescent device comprising the same.
An electroluminescent (EL) device is a self-light-emitting device with the advantage of providing a wider viewing angle, a greater contrast ratio, and a faster response time. An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer (see Appl. Phys. Lett. 51, 913, 1987).
The organic EL device changes electric energy into light by the injection of a charge into an organic light-emitting material and commonly comprises an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer of the organic EL device may be composed of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), a light-emitting layer (EML) (containing host and dopant materials), an electron buffer layer, a hole blocking layer (HBL), an electron transport layer (ETL), an electron injection layer (EIL), etc.; the materials used in the organic layer can be classified into a hole injection material, a hole transport material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc., depending on functions. In the organic EL device, holes from an anode and electrons from a cathode are injected into a light-emitting layer by the injection of a charge, and an exciton having high energy is produced by the recombination of holes and electrons. The organic light-emitting compound moves into an excited state by the energy and emits light which changes from energy when the organic light-emitting compound returns to the ground state from the excited state.
The most important factor determining luminescent efficiency in an organic EL device is the light-emitting material. The light-emitting material is required to have the following features: high quantum efficiency, high movement degree of an electron and a hole, formability of a uniform layer, and stability. The light-emitting material is classified into blue light-emitting materials, green light-emitting materials, and red light-emitting materials according to the light-emitting color, and further includes yellow light-emitting materials or orange light-emitting materials. Furthermore, the light-emitting material is classified into a host material and a dopant material in the functional aspect. Recently, an urgent task is the development of an organic EL device having high efficacy and long operating lifespan. In particular, the development of highly excellent light-emitting material over conventional light-emitting materials is urgent considering EL properties required in medium- and large-sized OLED panels. For this, preferably, as a solvent in a solid state and energy transmitter, a host material should have high purity and suitable molecular weight in order to be deposited under vacuum. Furthermore, a host material is required to have high glass transition temperature and pyrolysis temperature to guarantee thermal stability, high electrochemical stability to provide long lifespan, easy formability of an amorphous thin film, good adhesion with adjacent layers, and no movement between layers.
A mixed system of a dopant/host material can be used as a light-emitting material to improve color purity, luminescent efficiency, and stability. Generally, the device having the most excellent EL properties comprises the light-emitting layer, wherein a dopant is doped onto a host. If the dopant/host material system is used, the selection of the host material is important since the host material greatly influences on efficiency and performance of a light-emitting device.
WO 2013/168688 A1, Japanese Patent No. 3139321, Korean Patent No. 10-1170666, Korean Patent Application Laying-open No. 10-2012-0013173, and WO 2013/112557 A1 disclose organic EL devices comprising a dopant/host material system. The above literature use one host component having a carbazole-carbazole skeleton or exclude a host having a cabazole skeleton from second and third hosts.
The present inventors have found that an organic EL device using a multi-component host compounds having a specific bicarbazole derivative which contains an aryl group and a specific carbazole derivative which includes a nitrogen-containing heteroaryl group has high efficiency and long lifespan, compared with using one component host compound in a light-emitting layer.
The object of the present invention is to provide an organic EL device having high efficiency and long lifespan.
The above objective can be achieved by an organic electroluminescent device comprising at least one light-emitting layer between an anode and a cathode, wherein the light-emitting layer comprises a host and a phosphorescent dopant; the host consists of multi-component host compounds; at least a first host compound of the multi-component host compounds is represented by the following formula 1 which is a specific bicarbazole derivative containing an aryl group, and a second host compound is represented by the following formula 2 which is a specific carbazole derivative including a nitrogen-containing heteroaryl group:
Figure PCTKR2015003485-appb-I000001
Figure PCTKR2015003485-appb-I000002
wherein
A1 and A2 each independently represent a substituted or unsubstituted (C6-C30)aryl 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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino group; or are linked between adjacent substituents 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;
Ma represents a substituted or unsubstituted nitrogen-containing 5- to 30-membered heteroaryl group;
La represents a single bond, or a substituted or unsubstituted (C6-C30)arylene group;
Xa to Xh 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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino group; or are linked between adjacent substituents to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring whose carbon atom(s) ring may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
the fused aromatic or heteroaromatic ring is selected from the group consisting of benzene, indole, indene, benzofuran and benzothiophene, which may be further substituted with a (C1-C10)alkyl group or a (C6-C15)aryl group; and
the heteroaryl group contains at least one hetero atom selected from B, N, O, S, P(=O), Si and P.
According to the present invention, the organic EL device having high efficiency and long lifespan is provided and the production of a display device or a lighting device is possible by using the organic EL device.
Hereinafter, the present invention 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 compound of formula 1 is represented by the following formula 3, 4, 5, or 6:
Figure PCTKR2015003485-appb-I000003
Figure PCTKR2015003485-appb-I000004
Figure PCTKR2015003485-appb-I000005
Figure PCTKR2015003485-appb-I000006
wherein
A1, A2 and X1 to X16 are as defined in formula 1.
In formula 1, A1 and A2 each independently represent a substituted or unsubstituted (C6-C30)aryl group; preferably, a substituted or unsubstituted (C6-C18)aryl group; more preferably, a (C6-C18)aryl group which is unsubstituted or substituted with a (C1-C6)alkyl group, a (C6-C12)aryl group, or a tri(C6-C12)arylsilyl group ; and even more preferably, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, or fluoranthenyl.
In formula 1, 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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino group; or are linked between adjacent substituents to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring whose carbon atom(s) ring may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur; preferably, hydrogen, a substituted or unsubstituted (C6-C20)aryl group, a substituted or unsubstituted tri(C6-C12)arylsilyl group, or a substituted or unsubstituted 3- to 15-membered heteroaryl group; and more preferably, hydrogen, a substituted or unsubstituted (C6-C18)aryl group, an unsubstituted triphenylsilyl group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted dibenzofuran group.
The compound of formula 2 is represented by the following formula 7, 8, or 9:
Figure PCTKR2015003485-appb-I000007
Figure PCTKR2015003485-appb-I000008
Figure PCTKR2015003485-appb-I000009
wherein
V and W each independently represent a single bond, NR15, CR16R17, S, or O, provided that both V and W neither represent a single bond nor represent NR15;
A2 represents a substituted or unsubstituted (C6-C30)aryl group and may be bonded to Xn or Xo;
L3 and L4 each independently represent a single bond, or a substituted or unsubstituted (C6-C60)arylene group;
Xi represents 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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino group; or are linked between adjacent substituents to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring whose carbon atom(s) ring may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
Xj to Xz each independently represent hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, -NR5R6, or -SiR7R8R9; or are linked between adjacent substituents to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring whose carbon atom(s) ring may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
Ma, La, Xa, Xb, and Xe to Xh are as defined in formula 2;
R5 to R9 each independently represent hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group; or are linked between adjacent substituents to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring whose carbon atom(s) ring may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur; preferably, hydrogen, or a substituted or unsubstituted (C6-C25)aryl group; more preferably, hydrogen or an unsubstituted (C6-C18)aryl group; and specifically, hydrogen, an unsubstituted phenyl group, a biphenyl group, or a fluorenyl group;
R16 and R17 each independently represent hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group; and
R15 represents hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group; preferably, a substituted or unsubstituted (C6-C30)aryl group; and more preferably, a substituted or unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, or a substituted fluorenyl group.
In formula 2, La represents a single bond, or a substituted or unsubstituted (C6-C30)arylene group; preferably, a single bond, or a substituted or unsubstituted (C6-C12)arylene group; and more preferably, a single bond, a (C6-C12)arylene group which is unsubstituted or substituted with a tri(C6-C10)arylsilyl group or a (C6-C12)aryl group.
Furthermore, La represents a single bond, or is represented by one selected from the following formulas 10 to 19:
Figure PCTKR2015003485-appb-I000010
Figure PCTKR2015003485-appb-I000011
Figure PCTKR2015003485-appb-I000012
Figure PCTKR2015003485-appb-I000013
Figure PCTKR2015003485-appb-I000014
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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino group; or are linked between adjacent substituents to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring whose carbon atom(s) ring may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur; preferably, hydrogen, a cyano group, a substituted or unsubstituted (C6-C15)aryl group, a substituted or unsubstituted 10- to 20-membered heteroaryl group, or a substituted or unsubstituted tri(C6-C10)arylsilyl group; more preferably, hydrogen, a cyano group, a (C6-C15)aryl group which is unsubstituted or substituted with a tri(C6-C10)arylsilyl group, or a 10- to 20-membered heteroaryl group which is unsubstituted or substituted with a (C6-C15)aryl group.
In formula 2, Ma represents a substituted or unsubstituted nitrogen-containing 5- to 11-membered heteroaryl group; preferably, a substituted or unsubstituted nitrogen-containing 6- to 10-membered heteroaryl group; and more preferably, a nitrogen-containing 6- to 10-membered heteroaryl group which is substituted with a substituents(s) selected from the group consisting of an unsubstituted (C6-C18)aryl group, a (C6-C12)aryl group substituted with a cyano group, a (C6-C12)aryl group substituted with a (C1-C6)alkyl group, a (C6-C12)aryl group substituted with a tri(C6-C12)arylsilyl group, and a 6- to 15-membered heteroaryl group.
Furthermore, Ma represents a monocyclic-based heteroaryl group selected from the group consisting of pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., or a fused ring-based heteroaryl group selected from the group consisting of benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, naphthyridinyl, quinoxalinyl, carbazolyl, phenanthridinyl, etc.; preferably, triazinyl, pyrimidinyl, pyridyl, quinolyl, isoquinolyl, quinazolinyl, naphthyridinyl, or quinoxalinyl.
Herein, “(C1-C30)alkyl(ene)” is meant to be a linear or branched alkyl(ene) having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. “(C2-C30)alkenyl” is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. “(C2-C30)alkynyl” is a linear or branched alkynyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc. “(C3-C30)cycloalkyl” is a mono- or polycyclic hydrocarbon having 3 to 30 carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. “3- to 7-membered heterocycloalkyl” is a cycloalkyl having at least one heteroatom selected from the group consisting of B, N, O, S, P(=O), Si and P, preferably O, S and N, and 3 to 7, preferably 5 to 7 ring backbone atoms, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. “(C6-C30)aryl(ene)” is a monocyclic or fused ring derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, in which the number of carbon atoms is preferably 6 to 20, more preferably 6 to 15, and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc. “3- to 30-membered heteroaryl(ene)” is an aryl group having at least one, preferably 1 to 4 heteroatom selected from the group consisting of B, N, O, S, P(=O), Si and P, and 3 to 30 ring backbone atoms; is a monocyclic ring, or a fused ring condensed with at least one benzene ring; has preferably 3 to 20, more preferably 3 to 15 ring backbone atoms; 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 including 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 including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, etc. “Nitrogen-containing 5- to 30-membered heteroaryl(ene) group” is an aryl(ene) group having at least one heteroatom N and 5 to 30 ring backbone atoms. 5 to 20 ring backbone atoms and 1 to 4 heteroatom are preferable, and 5 to 15 ring backbone atoms are more preferable. It 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 including pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl including benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, etc. “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. Substituents of the substituted alkyl(ene) group, the substituted alkenyl group, the substituted alkynyl group, the substituted cycloalkyl group, the substituted aryl(ene) group, the substituted heteroaryl(ene) group, the substituted trialkylsilyl group, the substituted triarylsilyl group, the substituted dialkylarylsilyl group, the substituted mono- or di-arylamino group, or the substituted mono- or polycyclic, (C3-C30) 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 which is unsubstituted or substituted with a (C6-C30)aryl group; a (C6-C30)aryl group which is 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. Preferably, the substituents are each independently at least one selected from the group consisting of a (C1-C6)alkyl group; a 5- to 15-membered heteroaryl group; a (C6-C18)aryl group which is unsubstituted or substituted with a cyano group or a tri(C6-C12)arylsilyl group; a tri(C6-C12)arylsilyl group; and a (C1-C6)alkyl(C6-C12)aryl group.
The compound of formula 1 as a first host compound may be selected from the group consisting of following compounds, but is not limited thereto:
Figure PCTKR2015003485-appb-I000015
Figure PCTKR2015003485-appb-I000016
Figure PCTKR2015003485-appb-I000017
Figure PCTKR2015003485-appb-I000018
Figure PCTKR2015003485-appb-I000019
Figure PCTKR2015003485-appb-I000020
Figure PCTKR2015003485-appb-I000021
Figure PCTKR2015003485-appb-I000022
Figure PCTKR2015003485-appb-I000023
Figure PCTKR2015003485-appb-I000024
Figure PCTKR2015003485-appb-I000025
Figure PCTKR2015003485-appb-I000026
Figure PCTKR2015003485-appb-I000027
Figure PCTKR2015003485-appb-I000028
Figure PCTKR2015003485-appb-I000029
Figure PCTKR2015003485-appb-I000030
Figure PCTKR2015003485-appb-I000031
Figure PCTKR2015003485-appb-I000032
Figure PCTKR2015003485-appb-I000033
Figure PCTKR2015003485-appb-I000034
Figure PCTKR2015003485-appb-I000035
Figure PCTKR2015003485-appb-I000036
Figure PCTKR2015003485-appb-I000037
Figure PCTKR2015003485-appb-I000038
Figure PCTKR2015003485-appb-I000039
Figure PCTKR2015003485-appb-I000040
Figure PCTKR2015003485-appb-I000041
Figure PCTKR2015003485-appb-I000042
Figure PCTKR2015003485-appb-I000043
Figure PCTKR2015003485-appb-I000044
Figure PCTKR2015003485-appb-I000045
Figure PCTKR2015003485-appb-I000046
Figure PCTKR2015003485-appb-I000047
Figure PCTKR2015003485-appb-I000048
Figure PCTKR2015003485-appb-I000049
Figure PCTKR2015003485-appb-I000050
Figure PCTKR2015003485-appb-I000051
The compound of formula 2 as a second host compound may be selected from the group consisting of following compounds, but is not limited thereto:
Figure PCTKR2015003485-appb-I000052
Figure PCTKR2015003485-appb-I000053
Figure PCTKR2015003485-appb-I000054
Figure PCTKR2015003485-appb-I000055
Figure PCTKR2015003485-appb-I000056
Figure PCTKR2015003485-appb-I000057
Figure PCTKR2015003485-appb-I000058
Figure PCTKR2015003485-appb-I000059
Figure PCTKR2015003485-appb-I000060
Figure PCTKR2015003485-appb-I000061
Figure PCTKR2015003485-appb-I000062
Figure PCTKR2015003485-appb-I000063
Figure PCTKR2015003485-appb-I000064
Figure PCTKR2015003485-appb-I000065
Figure PCTKR2015003485-appb-I000066
Figure PCTKR2015003485-appb-I000067
Figure PCTKR2015003485-appb-I000068
Figure PCTKR2015003485-appb-I000069
Figure PCTKR2015003485-appb-I000070
Figure PCTKR2015003485-appb-I000071
Figure PCTKR2015003485-appb-I000072
Figure PCTKR2015003485-appb-I000073
Figure PCTKR2015003485-appb-I000074
Figure PCTKR2015003485-appb-I000075
Figure PCTKR2015003485-appb-I000076
Figure PCTKR2015003485-appb-I000077
Figure PCTKR2015003485-appb-I000078
Figure PCTKR2015003485-appb-I000079
Figure PCTKR2015003485-appb-I000080
Figure PCTKR2015003485-appb-I000081
Figure PCTKR2015003485-appb-I000082
Figure PCTKR2015003485-appb-I000083
Figure PCTKR2015003485-appb-I000084
Figure PCTKR2015003485-appb-I000085
Figure PCTKR2015003485-appb-I000086
Figure PCTKR2015003485-appb-I000087
Figure PCTKR2015003485-appb-I000088
Figure PCTKR2015003485-appb-I000089
Figure PCTKR2015003485-appb-I000090
Figure PCTKR2015003485-appb-I000091
Figure PCTKR2015003485-appb-I000092
Figure PCTKR2015003485-appb-I000093
Figure PCTKR2015003485-appb-I000094
Figure PCTKR2015003485-appb-I000095
Figure PCTKR2015003485-appb-I000096
Figure PCTKR2015003485-appb-I000097
Figure PCTKR2015003485-appb-I000098
Figure PCTKR2015003485-appb-I000099
Figure PCTKR2015003485-appb-I000100
Figure PCTKR2015003485-appb-I000101
Figure PCTKR2015003485-appb-I000102
Figure PCTKR2015003485-appb-I000103
Figure PCTKR2015003485-appb-I000104
Figure PCTKR2015003485-appb-I000105
Figure PCTKR2015003485-appb-I000106
Figure PCTKR2015003485-appb-I000107
Figure PCTKR2015003485-appb-I000108
Figure PCTKR2015003485-appb-I000109
Figure PCTKR2015003485-appb-I000110
Figure PCTKR2015003485-appb-I000111
Figure PCTKR2015003485-appb-I000112
Figure PCTKR2015003485-appb-I000113
Figure PCTKR2015003485-appb-I000114
Figure PCTKR2015003485-appb-I000115
Figure PCTKR2015003485-appb-I000116
Figure PCTKR2015003485-appb-I000117
Figure PCTKR2015003485-appb-I000118
Figure PCTKR2015003485-appb-I000119
Figure PCTKR2015003485-appb-I000120
Figure PCTKR2015003485-appb-I000121
Figure PCTKR2015003485-appb-I000122
Figure PCTKR2015003485-appb-I000123
Figure PCTKR2015003485-appb-I000124
Figure PCTKR2015003485-appb-I000125
Figure PCTKR2015003485-appb-I000126
Figure PCTKR2015003485-appb-I000127
Figure PCTKR2015003485-appb-I000128
Figure PCTKR2015003485-appb-I000129
Figure PCTKR2015003485-appb-I000130
Figure PCTKR2015003485-appb-I000131
Figure PCTKR2015003485-appb-I000132
Figure PCTKR2015003485-appb-I000133
Figure PCTKR2015003485-appb-I000134
Figure PCTKR2015003485-appb-I000135
Figure PCTKR2015003485-appb-I000136
Figure PCTKR2015003485-appb-I000137
Figure PCTKR2015003485-appb-I000138
Figure PCTKR2015003485-appb-I000139
Figure PCTKR2015003485-appb-I000140
Figure PCTKR2015003485-appb-I000141
Figure PCTKR2015003485-appb-I000142
Figure PCTKR2015003485-appb-I000143
Figure PCTKR2015003485-appb-I000144
The organic EL device according to the present invention may comprise an anode, a cathode, and at least one organic layer between the two electrodes, wherein the organic layer comprises a light-emitting layer, the light-emitting layer comprises a host and a phosphorescent dopant; the host consists of multi-component host compounds; at least a first host compound of the multi-component host compounds is represented by formula 1 which is a specific bicarbazole derivative containing an aryl group, and a second host compound is represented by formula 2 which is a specific carbazole derivative including a nitrogen-containing heteroaryl group.
The light-emitting layer means a layer emitting light and may be a single layer or multi-layers consisting of two or more layers. The doping concentration of dopant compounds to host compounds in the light-emitting layer is preferably less than 20 wt%.
The dopants included in the organic EL device of the present invention are preferably one or more phosphorescent dopants. The phosphorescent dopant material applied to the organic electroluminescent device of the present invention is not specifically limited, but preferably may be selected from complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably ortho metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho metallated iridium complex compounds.
The phosphorescent dopants may be selected from the group consisting of the compounds represented by the following formulae 101 to 103:
Figure PCTKR2015003485-appb-I000145
Figure PCTKR2015003485-appb-I000146
Figure PCTKR2015003485-appb-I000147
wherein
L is selected from the following structures:
Figure PCTKR2015003485-appb-I000148
R100 represents hydrogen, or a substituted or unsubstituted (C1-C30)alkyl group; R101 to R109 and R111 to R123 each independently represent hydrogen, deuterium, a halogen; a (C1-C30)alkyl group unsubstituted or substituted with halogen(s); a cyano group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group; R120 to R123 are linked to an adjacent substituent(s) to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, for example, quinoline; 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; when R124 to R127 are aryl groups, they are linked to an adjacent substituent(s) to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, or a heteroaromatic ring, for example, fluorene, dibenzothiophene, or dibenzofuran; R201 to R211 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), or a substituted or unsubstituted (C6-C30)aryl group; R208 to R211 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, or a heteroaromatic ring, for example, fluorene, dibenzothiophene, or dibenzofuran; r and s each independently represent an integer of 1 to 3; where 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.
The phosphorescent dopant material includes the following:
Figure PCTKR2015003485-appb-I000149
Figure PCTKR2015003485-appb-I000150
Figure PCTKR2015003485-appb-I000151
Figure PCTKR2015003485-appb-I000152
Figure PCTKR2015003485-appb-I000153
Figure PCTKR2015003485-appb-I000154
Figure PCTKR2015003485-appb-I000155
Figure PCTKR2015003485-appb-I000156
Figure PCTKR2015003485-appb-I000157
Figure PCTKR2015003485-appb-I000158
Figure PCTKR2015003485-appb-I000159
Figure PCTKR2015003485-appb-I000160
Figure PCTKR2015003485-appb-I000161
Figure PCTKR2015003485-appb-I000162
Figure PCTKR2015003485-appb-I000163
Figure PCTKR2015003485-appb-I000164
Figure PCTKR2015003485-appb-I000165
Figure PCTKR2015003485-appb-I000166
Figure PCTKR2015003485-appb-I000167
Figure PCTKR2015003485-appb-I000168
Figure PCTKR2015003485-appb-I000169
Figure PCTKR2015003485-appb-I000170
Figure PCTKR2015003485-appb-I000171
Figure PCTKR2015003485-appb-I000172
Figure PCTKR2015003485-appb-I000173
Figure PCTKR2015003485-appb-I000174
Figure PCTKR2015003485-appb-I000175
The organic EL device of the present invention may further include at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds in the organic layer.
In the organic EL device of the present invention, 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 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 invention, at least one layer (hereinafter, "a surface layer”) selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on an inner surface(s) of one or both electrode(s). Specifically, it is preferred that a chalcogenide (including oxides) layer of silicon or aluminum is placed on an anode surface of a light-emitting medium layer, and a metal halide layer or metal oxide layer is placed on a cathode surface of an electroluminescent medium layer. The surface layer provides operating 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 their combinations can be used between an anode and a light-emitting layer. The hole injection layer may be multi-layers in order to lower a hole injection barrier (or hole injection voltage) from an anode to a hole transport layer or an electron blocking layer, wherein each of the multi-layers simultaneously uses two compounds. The hole transport layer or the electron blocking layer may also be multi-layers.
An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or their combinations can be used between a light-emitting layer and a cathode. The electron buffer layer may be multi-layers in order to control the injection of an electron and improve interface properties between the light-emitting layer and the electron injection layer, wherein each of the multi-layers simultaneously uses two compounds. The hole blocking layer or the electron transport layer may also be multi-layers, wherein each of the multi-layers may use a multi-component of compounds.
Preferably, in the organic electroluminescent device of the present invention, 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 a light-emitting medium. Further, the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to a light-emitting 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 organic electroluminescent device having two or more light-emitting layers and emitting white light.
In order to form each layer constituting the organic electroluminescent device of the present invention, dry film-forming methods, such as vacuum deposition, sputtering, plasma, ion plating methods, etc., or wet film-forming methods, such as spin coating, dip coating, flow coating methods, etc., can be used. When forming a layer by using a first host and a second host according to the present invention, co-deposition or mixed-deposition may be used.
When using a wet film-forming method, a thin film is formed by dissolving or dispersing the material constituting each layer in suitable solvents, such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvents are not specifically limited as long as the material constituting each layer is soluble or dispersible in the solvents, which do not cause any problems in forming a layer.
Furthermore, a display device or a light device can be produced by using the organic EL device of the present invention.
Hereinafter, the preparation methods of devices by using host compounds and dopant compounds of the present invention will be explained in detail with reference to the following examples:
Device Example 1-1: Production of an OLED device by co-deposition of the first host compound and the second host compound according to the present invention as a host
An OLED device comprising the organic electroluminescent compound of the present invention was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (10 Ω/sq) on a glass substrate for an OLED device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and was then stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus. N4,N4’-diphenyl-N4,N4’-bis(9-phenyl-9H-carbazole-3-yl)-[1,1’-biphenyl]-4,4’-diamine as HI-1 was introduced into a cell of the vacuum vapor depositing apparatus, and the pressure in the chamber of the apparatus was then controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming a hole injection layer 1 having a thickness of 80 nm on the ITO substrate. 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile as HI-2 was then introduced into another cell of the vacuum vapor depositing apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming a hole injection layer 2 having a thickness of 5 nm on hole injection layer 1. N-([1,1’-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine as HT-1 was introduced into one cell of the vacuum vapor depositing apparatus. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming a hole transport layer 1 having a thickness of 10 nm on hole injection layer 2. N,N-di([1,1’-biphenyl]-4-yl)-4’-(9H-carbazole-9-yl)-[1,1’-biphenyl]-4-amine as HT-2 was then introduced into another cell of the vacuum vapor depositing apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming a hole transport layer 2 having a thickness of 60 nm on hole transport layer 1. Thereafter, compounds H1-1 and H2-2 as hosts were respectively introduced into two cells of the vacuum vapor depositing apparatus and compound D-96 as a dopant was introduced into another cell. The two host materials were evaporated at the same rates of 1:1, and the dopant was evaporated at a different rate and deposited in a doping amount of 3 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 40 nm on the hole transport layer. Next, 2,4-bis(9,9-dimethyl-9H-fluorene-2yl)-6-(naphthalene-2-yl)-1,3,5-triazine as ET-1 and lithium quinolate as EI-1 were evaporated at the same rates of 1:1 on another two cells to form an electron transport layer having a thickness of 30 nm on the light-emitting layer. After depositing lithium quinolate of 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 device was produced.
The produced OLED device showed the driving voltage at a luminance of 1,000nit, luminescent efficiency, CIE color coordinate, and the lifespan taken to be reduced from 100% to 90% of the constant current at a luminance of 5,000nit as provided in Table 1 below.
Figure PCTKR2015003485-appb-I000176
Comparative Example 1-1: Production of an OLED device by using only the second host compound according to the present invention as a host
An OLED device was produced in the same manner as in Device Example 1-1, except that only the second host compound was used as a host in a light-emitting layer.
The luminescent properties of the OLED devices produced in Device Example 1-1 and Comparative Example 1-1 are provided in Table 1 below.
Table 1
Figure PCTKR2015003485-appb-I000177
Device Examples 2-1 to 2-13: Production of an OLED device by co -deposition of the first host compound and the second host compound according to the present invention as a host
An OLED device was produced in the same manner as in Device Example 1-1, except that hole injection layer 2 has a thickness of 3 nm, hole transport layer 1 has a thickness of 40 nm, hole transport layer 2 is not present, D-25 as a dopant was deposited in a doping amount on 15wt% in a light-emitting layer, the electron transport layer having a thickness of 35 nm was deposited via the evaporation rate of 4:6, the combinations of the first host compound and the second host compound used as hosts in a light-emitting layer are based on Device Examples 2-1 to 2-13 as provided in Table 2 below, and the lifespan taken to be reduced from 100% to 90% of the constant current at a luminance of 15,000nit as provided in Table 2 below.
Device Examples 2-14 to 2-18: Production of an OLED device by co-deposition of the first host compound and the second host compound according to the present invention as a host
An OLED device was produced in the same manner as in Device Examples 2-1 to 2-13, except that hole injection layer 2 has a thickness of 3 nm, hole transport layer 1 has a thickness of 40 nm, hole transport layer 2 is not present, D-1 as a dopant was used in a light-emitting layer, the electron transport layer having a thickness of 35 nm was deposited via the evaporation rate of 4:6, the combinations of the first host compound and the second host compound used as hosts in a light-emitting layer are based on Device Examples 2-14 to 2-18 as provided in Table 2 below, and the lifespan taken to be reduced from 100% to 90% of the constant current at a luminance of 15,000nit as provided in Table 2 below.
Device Examples 3-1 to 3-8: Production of an OLED device by co -deposition of the first host compound and the second host compound according to the present invention as a host
An OLED device was produced in the same manner as in Device Examples 2-1 to 2-13, except that hole transport layer 1 has a thickness of 10 nm, hole transport layer 2 of HT-3 has a thickness of 30 nm, D-136 as a dopant was used in a light-emitting layer, and the combinations of the first host compound and the second host compound used as hosts in a light-emitting layer are based on Device Examples 3-1 to 3-8 as provided in Table 2 below.
Device Example 3-9: Production of an OLED device by co-deposition of the first host compound and the second host compound according to the present invention as a host
An OLED device was produced in the same manner as in Device Examples 2-1 to 2-13, except that hole transport layer 1 has a thickness of 10 nm, hole transport layer 2 of HT-3 has a thickness of 30 nm, D-164 as a dopant was used in a light-emitting layer, and the combinations of the first host compound and the second host compound used as hosts in a light-emitting layer are based on Device Example 3-9 as provided in Table 2 below.
Device Examples 3-10 to 3-12: Production of an OLED device by co-deposition of the first host compound and the second host compound according to the present invention as a host
An OLED device was produced in the same manner as in Device Examples 2-1 to 2-13, except that hole transport layer 1 has a thickness of 10 nm, hole transport layer 2 of HT-3 has a thickness of 30 nm, D-168 as a dopant was used in a light-emitting layer, and the combinations of the first host compound and the second host compound used as hosts in a light-emitting layer are based on Device Examples 3-10 to 3-12 as provided in Table 2 below.
Device Example 3-13: Production of an OLED device by co-deposition of the first host compound and the second host compound according to the present invention as a host
An OLED device was produced in the same manner as in Device Examples 2-1 to 2-13, except that hole transport layer 1 has a thickness of 10 nm, hole transport layer 2 of HT-3 has a thickness of 30 nm, D-180 as a dopant was used in a light-emitting layer, and the combinations of the first host compound and the second host compound used as hosts in a light-emitting layer are based on Device Example 3-13 as provided in Table 2 below.
Comparative Examples 2-1 to 2-3: Production of an OLED device by using only the first host compound according to the present invention as a host
An OLED device was produced in the same manner as in Device Examples 2-1 to 2-13, except that the first host compound used as hosts in a light-emitting layer is based on Comparative Examples 2-1 to 2-3 as provided in Table 2 below.
Comparative Examples 3-1 to 3-9: Production of an OLED device by using only the second host compound according to the present invention as a host
An OLED device was produced in the same manner as in Device Examples 2-1 to 2-13, except that the second host compound used as hosts in a light-emitting layer is based on Comparative Examples 3-1 to 3-9 as provided in Table 2 below.
Comparative Example 4-1: Production of an OLED device by using only the second host compound according to the present invention as a host
An OLED device was produced in the same manner as in Device Examples 3-1 to 3-8, except that the second host compound used as hosts in a light-emitting layer is based on Comparative Example 4-1 as provided in Table 2 below.
The luminescent properties of the OLED devices produced in the above Device Examples and Comparative Examples are provided in Table 2 below.
Table 2
Figure PCTKR2015003485-appb-I000178
Figure PCTKR2015003485-appb-I000179
Figure PCTKR2015003485-appb-I000180
Figure PCTKR2015003485-appb-I000181
Device Examples 4-1 to 4-7: Production of an OLED device by co -deposition of the first host compound and the second host compound according to the present invention as a host
An OLED device was produced in the same manner as in Device Example 1-1, except that HT-4 was used as a hole transport layer 2, the combinations of the first host compound and the second host compound used as hosts in a light-emitting layer are based on Device Examples 4-1 to 4-7 as provided in Table 3 below, and the lifespan taken to be reduced from 100% to 95% of the constant current at a luminance of 5,000nit as provided in Table 3 below.
Figure PCTKR2015003485-appb-I000182
Comparative Examples 5-1 and 5-2: Production of an OLED device by using only the second host compound according to the present invention as a host
An OLED device was produced in the same manner as in Device Examples 4-1 to 4-7, except that the second host compound used as hosts in a light-emitting layer is based on Comparative Examples 5-1 and 5-2 as provided in Table 3 below.
The luminescent properties of the OLED devices produced in Device Examples 4-1 to 4-7, and Comparative Examples 5-1 and 5-2 are provided in Table 3 below.
Table 3
Figure PCTKR2015003485-appb-I000183
Device Examples 5-1 and 5-2: Production of an OLED device by co -deposition of the first host compound and the second host compound according to the present invention as a host
An OLED device was produced in the same manner as in Device Examples 3-1 to 3-11, except that D-134 was used as a dopant in a light-emitting layer, the combinations of the first host compound and the second host compound used as hosts in a light-emitting layer are based on Device Examples 5-1 and 5-2 as provided in Table 4 below, and the lifespan taken to be reduced from 100% to 97% of the constant current at a luminance of 15,000nit as provided in Table 4 below.
Comparative Examples 6-1 and 6-2: Production of an OLED device by using only the first host compound according to the present invention as a host
An OLED device was produced in the same manner as in Device Examples 5-1 and 5-2, except that the first host compound used as hosts in a light-emitting layer is based on Comparative Examples 6-1 and 6-2 as provided in Table 4 below.
Comparative Example 7-1: Production of an OLED device by using only the second host compound according to the present invention as a host
An OLED device was produced in the same manner as in Device Examples 5-1 and 5-2, except that the second host compound used as hosts in a light-emitting layer is based on Comparative Example 7-1 as provided in Table 4 below.
The luminescent properties of the OLED devices produced in Device Examples 5-1 and 5-2, Comparative Examples 6-1 and 6-2, and Comparative Example 7-1 are provided in Table 4 below.
Table 4
Figure PCTKR2015003485-appb-I000184
The organic electroluminescent device of the present invention provides longer lifespan compared with conventional devices by comprising a light-emitting layer containing a host and a phosphorescent dopant, wherein the host consists of multi-component host compounds, at least a first host compound of the multi-component host compounds has a specific bicarbazole derivative containing an aryl group, and a second host compound has a specific carbazole derivative including a nitrogen-containing heteroaryl group.

Claims (10)

  1. An organic electroluminescent device comprising at least one light-emitting layer between an anode and a cathode, wherein the light-emitting layer comprises a host and a phosphorescent dopant; the host consists of multi-component host compounds; at least a first host compound of the multi-component host compounds is represented by the following formula 1 which is a bicarbazole derivative containing an aryl group, and a second host compound is represented by the following formula 2 which is a carbazole derivative including a nitrogen-containing heteroaryl group:
    Figure PCTKR2015003485-appb-I000185
    Figure PCTKR2015003485-appb-I000186
    wherein
    A1 and A2 each independently represent a substituted or unsubstituted (C6-C30)aryl 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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino group; or are linked between adjacent substituents 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;
    Ma represents a substituted or unsubstituted nitrogen-containing 5- to 30-membered heteroaryl group;
    La represents a single bond, or a substituted or unsubstituted (C6-C30)arylene group;
    Xa to Xh 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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino group; or are linked between adjacent substituents to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring whose carbon atom(s) ring may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
    the fused aromatic or heteroaromatic ring is selected from the group consisting of benzene, indole, indene, benzofuran and benzothiophene, which may be further substituted with a (C1-C10)alkyl group or a (C6-C15)aryl group; and
    the heteroaryl group contains at least one hetero atom selected from B, N, O, S, P(=O), Si and P.
  2. The organic electroluminescent device according to claim 1, wherein the compound of formula 1 is represented by the following formula 3, 4, 5, or 6:
    Figure PCTKR2015003485-appb-I000187
    Figure PCTKR2015003485-appb-I000188
    Figure PCTKR2015003485-appb-I000189
    Figure PCTKR2015003485-appb-I000190
    wherein
    A1 and A2 each independently represent a substituted or unsubstituted (C6-C30)aryl group; and
    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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino group; or are linked between adjacent substituents to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring whose carbon atom(s) ring may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur.
  3. The organic electroluminescent device according to claim 1, wherein the compound of formula 2 is represented by the following formula 7, 8, or 9:
    Figure PCTKR2015003485-appb-I000191
    Figure PCTKR2015003485-appb-I000192
    Figure PCTKR2015003485-appb-I000193
    wherein
    V and W each independently represent a single bond, NR15, CR16R17, S, or O, provided that both V and W neither represent a single bond nor represent NR15;
    A2 represents a substituted or unsubstituted (C6-C30)aryl group and may be bonded to Xn or Xo;
    L3 and L4 each independently represent a single bond, or a substituted or unsubstituted (C6-C60)arylene group;
    Xi represents 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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino group; or are linked between adjacent substituents to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring whose carbon atom(s) ring may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
    Xj to Xz each independently represent hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, -NR5R6, or -SiR7R8R9; or are linked between adjacent substituents to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring whose carbon atom(s) ring may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
    Ma, La, Xa, Xb, and Xe to Xh are as defined in formula 2;
    R5 to R9 each independently represent hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group; or are linked between adjacent substituents to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring whose carbon atom(s) ring may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
    R16 and R17 each independently represent hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group; and
    R15 represents hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C60)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group.
  4. The organic electroluminescent device according to claim 1, wherein La in formula 2 represents a single bond, or is represented by one selected from the following formulas 10 to 19:
    Figure PCTKR2015003485-appb-I000194
    Figure PCTKR2015003485-appb-I000195
    Figure PCTKR2015003485-appb-I000196
    Figure PCTKR2015003485-appb-I000197
    Figure PCTKR2015003485-appb-I000198
    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, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino group; or are linked between adjacent substituents to form a substituted or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring whose carbon atom(s) ring may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur.
  5. The organic electroluminescent device according to claim 1, wherein Ma in formula 2 is a monocyclic-based heteroaryl group selected from the group consisting of pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, or a fused ring-based heteroaryl group selected from the group consisting of benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, naphthyridinyl, quinoxalinyl, carbazolyl and phenanthridinyl.
  6. The organic electroluminescent device according to claim 1, wherein A1 and A2 in formula 1 each independently represent phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, or fluoranthenyl.
  7. The organic electroluminescent device according to claim 1, wherein Xa to Xh in formula 2 each independently represent hydrogen; a cyano group; a (C6-C15)aryl group which is unsubstituted or substituted with a tri(C6-C10)arylsilyl group, or a 10- to 20-membered heteroaryl group which is unsubstituted or substituted with a (C6-C12)aryl group; or are linked between adjacent substituents to form a substituted or unsubstituted benzene, a substituted or unsubstituted indole, a substituted or unsubstituted indene, a substituted or unsubstituted benzofuran, or a substituted or unsubstituted benzothiophene.
  8. The organic electroluminescent device according to claim 1, wherein the triarylsilyl as X1 to X16 in formula 1 is triphenylsilyl.
  9. The organic electroluminescent device according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of the following compounds:
    Figure PCTKR2015003485-appb-I000199
    Figure PCTKR2015003485-appb-I000200
    Figure PCTKR2015003485-appb-I000201
    Figure PCTKR2015003485-appb-I000202
    Figure PCTKR2015003485-appb-I000203
    Figure PCTKR2015003485-appb-I000204
    Figure PCTKR2015003485-appb-I000205
    Figure PCTKR2015003485-appb-I000206
    Figure PCTKR2015003485-appb-I000207
    Figure PCTKR2015003485-appb-I000208
    Figure PCTKR2015003485-appb-I000209
    Figure PCTKR2015003485-appb-I000210
    Figure PCTKR2015003485-appb-I000211
    Figure PCTKR2015003485-appb-I000212
    Figure PCTKR2015003485-appb-I000213
    Figure PCTKR2015003485-appb-I000214
    Figure PCTKR2015003485-appb-I000215
    Figure PCTKR2015003485-appb-I000216
    Figure PCTKR2015003485-appb-I000217
    Figure PCTKR2015003485-appb-I000218
    Figure PCTKR2015003485-appb-I000219
    Figure PCTKR2015003485-appb-I000220
    Figure PCTKR2015003485-appb-I000221
    Figure PCTKR2015003485-appb-I000222
    Figure PCTKR2015003485-appb-I000223
    Figure PCTKR2015003485-appb-I000224
    Figure PCTKR2015003485-appb-I000225
    Figure PCTKR2015003485-appb-I000226
    Figure PCTKR2015003485-appb-I000227
    Figure PCTKR2015003485-appb-I000228
    Figure PCTKR2015003485-appb-I000229
    Figure PCTKR2015003485-appb-I000230
    Figure PCTKR2015003485-appb-I000231
    Figure PCTKR2015003485-appb-I000232
    Figure PCTKR2015003485-appb-I000233
    Figure PCTKR2015003485-appb-I000234
    Figure PCTKR2015003485-appb-I000235
  10. The organic electroluminescent device according to claim 1, wherein the compound represented by formula 2 is selected from the group consisting of the following compounds:
    Figure PCTKR2015003485-appb-I000236
    Figure PCTKR2015003485-appb-I000237
    Figure PCTKR2015003485-appb-I000238
    Figure PCTKR2015003485-appb-I000239
    Figure PCTKR2015003485-appb-I000240
    Figure PCTKR2015003485-appb-I000241
    Figure PCTKR2015003485-appb-I000242
    Figure PCTKR2015003485-appb-I000243
    Figure PCTKR2015003485-appb-I000244
    Figure PCTKR2015003485-appb-I000245
    Figure PCTKR2015003485-appb-I000246
    Figure PCTKR2015003485-appb-I000247
    Figure PCTKR2015003485-appb-I000248
    Figure PCTKR2015003485-appb-I000249
    Figure PCTKR2015003485-appb-I000250
    Figure PCTKR2015003485-appb-I000251
    Figure PCTKR2015003485-appb-I000252
    Figure PCTKR2015003485-appb-I000253
    Figure PCTKR2015003485-appb-I000254
    Figure PCTKR2015003485-appb-I000255
    Figure PCTKR2015003485-appb-I000256
    Figure PCTKR2015003485-appb-I000257
    Figure PCTKR2015003485-appb-I000258
    Figure PCTKR2015003485-appb-I000259
    Figure PCTKR2015003485-appb-I000260
    Figure PCTKR2015003485-appb-I000261
    Figure PCTKR2015003485-appb-I000262
    Figure PCTKR2015003485-appb-I000263
    Figure PCTKR2015003485-appb-I000264
    Figure PCTKR2015003485-appb-I000265
    Figure PCTKR2015003485-appb-I000266
    Figure PCTKR2015003485-appb-I000267
    Figure PCTKR2015003485-appb-I000268
    Figure PCTKR2015003485-appb-I000269
    Figure PCTKR2015003485-appb-I000270
    Figure PCTKR2015003485-appb-I000271
    Figure PCTKR2015003485-appb-I000272
    Figure PCTKR2015003485-appb-I000273
    Figure PCTKR2015003485-appb-I000274
    Figure PCTKR2015003485-appb-I000275
    Figure PCTKR2015003485-appb-I000276
    Figure PCTKR2015003485-appb-I000277
    Figure PCTKR2015003485-appb-I000278
    Figure PCTKR2015003485-appb-I000279
    Figure PCTKR2015003485-appb-I000280
    Figure PCTKR2015003485-appb-I000281
    Figure PCTKR2015003485-appb-I000282
    Figure PCTKR2015003485-appb-I000283
    Figure PCTKR2015003485-appb-I000284
    Figure PCTKR2015003485-appb-I000285
    Figure PCTKR2015003485-appb-I000286
    Figure PCTKR2015003485-appb-I000287
    Figure PCTKR2015003485-appb-I000288
    Figure PCTKR2015003485-appb-I000289
    Figure PCTKR2015003485-appb-I000290
    Figure PCTKR2015003485-appb-I000291
    Figure PCTKR2015003485-appb-I000292
    Figure PCTKR2015003485-appb-I000293
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    Figure PCTKR2015003485-appb-I000312
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    Figure PCTKR2015003485-appb-I000319
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    Figure PCTKR2015003485-appb-I000328
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