US20170117488A1 - 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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US20170117488A1
US20170117488A1 US15/301,978 US201515301978A US2017117488A1 US 20170117488 A1 US20170117488 A1 US 20170117488A1 US 201515301978 A US201515301978 A US 201515301978A US 2017117488 A1 US2017117488 A1 US 2017117488A1
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substituted
unsubstituted
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alkyl
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Hee-Choon Ahn
Young-Kwan 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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Rohm and Haas Electronic Materials Korea Ltd
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Priority claimed from PCT/KR2015/003485 external-priority patent/WO2015156587A1/en
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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 heteroaryl group contains at least one hetero atom selected from B, N, O, S, P( ⁇ O), Si and P.
  • 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.
  • “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, tetraziny
  • “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.
  • At least one 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.
  • 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 n/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 1,000 nit, luminescent efficiency, CIE color coordinate, and the lifespan taken to be reduced from 100% to 90% of the constant current at a luminance of 5,000 nit 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.
  • 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 15 wt % 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 15,000 nit 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 15,000 nit 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-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.
  • 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.
  • 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 5,000 nit 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.
  • 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 15,000 nit 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.

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

    TECHNICAL FIELD
  • The present invention relates to a multi-component host material and an organic electroluminescent device comprising the same.
    • BACKGROUND ART
  • 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.
    • DISCLOSURE OF THE INVENTION Problems to be Solved
  • The object of the present invention is to provide an organic EL device having high efficiency and long lifespan.
    • Solution to Problems
  • 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 US20170117488A1-20170427-C00001
  • 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.
    • Effects of the Invention
  • 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.
    • EMBODIMENTS OF THE INVENTION
  • 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 US20170117488A1-20170427-C00002
  • 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 US20170117488A1-20170427-C00003
  • 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 US20170117488A1-20170427-C00004
    Figure US20170117488A1-20170427-C00005
  • 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, C1, 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 US20170117488A1-20170427-C00006
    Figure US20170117488A1-20170427-C00007
    Figure US20170117488A1-20170427-C00008
    Figure US20170117488A1-20170427-C00009
    Figure US20170117488A1-20170427-C00010
    Figure US20170117488A1-20170427-C00011
    Figure US20170117488A1-20170427-C00012
    Figure US20170117488A1-20170427-C00013
    Figure US20170117488A1-20170427-C00014
    Figure US20170117488A1-20170427-C00015
    Figure US20170117488A1-20170427-C00016
    Figure US20170117488A1-20170427-C00017
    Figure US20170117488A1-20170427-C00018
    Figure US20170117488A1-20170427-C00019
    Figure US20170117488A1-20170427-C00020
    Figure US20170117488A1-20170427-C00021
    Figure US20170117488A1-20170427-C00022
    Figure US20170117488A1-20170427-C00023
    Figure US20170117488A1-20170427-C00024
    Figure US20170117488A1-20170427-C00025
    Figure US20170117488A1-20170427-C00026
    Figure US20170117488A1-20170427-C00027
    Figure US20170117488A1-20170427-C00028
    Figure US20170117488A1-20170427-C00029
    Figure US20170117488A1-20170427-C00030
    Figure US20170117488A1-20170427-C00031
    Figure US20170117488A1-20170427-C00032
    Figure US20170117488A1-20170427-C00033
    Figure US20170117488A1-20170427-C00034
    Figure US20170117488A1-20170427-C00035
    Figure US20170117488A1-20170427-C00036
    Figure US20170117488A1-20170427-C00037
    Figure US20170117488A1-20170427-C00038
    Figure US20170117488A1-20170427-C00039
    Figure US20170117488A1-20170427-C00040
    Figure US20170117488A1-20170427-C00041
    Figure US20170117488A1-20170427-C00042
    Figure US20170117488A1-20170427-C00043
    Figure US20170117488A1-20170427-C00044
    Figure US20170117488A1-20170427-C00045
    Figure US20170117488A1-20170427-C00046
    Figure US20170117488A1-20170427-C00047
    Figure US20170117488A1-20170427-C00048
    Figure US20170117488A1-20170427-C00049
    Figure US20170117488A1-20170427-C00050
    Figure US20170117488A1-20170427-C00051
    Figure US20170117488A1-20170427-C00052
    Figure US20170117488A1-20170427-C00053
    Figure US20170117488A1-20170427-C00054
    Figure US20170117488A1-20170427-C00055
    Figure US20170117488A1-20170427-C00056
    Figure US20170117488A1-20170427-C00057
    Figure US20170117488A1-20170427-C00058
    Figure US20170117488A1-20170427-C00059
    Figure US20170117488A1-20170427-C00060
    Figure US20170117488A1-20170427-C00061
    Figure US20170117488A1-20170427-C00062
    Figure US20170117488A1-20170427-C00063
    Figure US20170117488A1-20170427-C00064
    Figure US20170117488A1-20170427-C00065
    Figure US20170117488A1-20170427-C00066
    Figure US20170117488A1-20170427-C00067
    Figure US20170117488A1-20170427-C00068
    Figure US20170117488A1-20170427-C00069
    Figure US20170117488A1-20170427-C00070
    Figure US20170117488A1-20170427-C00071
    Figure US20170117488A1-20170427-C00072
    Figure US20170117488A1-20170427-C00073
    Figure US20170117488A1-20170427-C00074
    Figure US20170117488A1-20170427-C00075
    Figure US20170117488A1-20170427-C00076
    Figure US20170117488A1-20170427-C00077
    Figure US20170117488A1-20170427-C00078
    Figure US20170117488A1-20170427-C00079
    Figure US20170117488A1-20170427-C00080
    Figure US20170117488A1-20170427-C00081
    Figure US20170117488A1-20170427-C00082
    Figure US20170117488A1-20170427-C00083
    Figure US20170117488A1-20170427-C00084
    Figure US20170117488A1-20170427-C00085
    Figure US20170117488A1-20170427-C00086
    Figure US20170117488A1-20170427-C00087
    Figure US20170117488A1-20170427-C00088
    Figure US20170117488A1-20170427-C00089
    Figure US20170117488A1-20170427-C00090
    Figure US20170117488A1-20170427-C00091
    Figure US20170117488A1-20170427-C00092
    Figure US20170117488A1-20170427-C00093
    Figure US20170117488A1-20170427-C00094
    Figure US20170117488A1-20170427-C00095
    Figure US20170117488A1-20170427-C00096
    Figure US20170117488A1-20170427-C00097
    Figure US20170117488A1-20170427-C00098
    Figure US20170117488A1-20170427-C00099
    Figure US20170117488A1-20170427-C00100
    Figure US20170117488A1-20170427-C00101
    Figure US20170117488A1-20170427-C00102
    Figure US20170117488A1-20170427-C00103
    Figure US20170117488A1-20170427-C00104
    Figure US20170117488A1-20170427-C00105
    Figure US20170117488A1-20170427-C00106
    Figure US20170117488A1-20170427-C00107
    Figure US20170117488A1-20170427-C00108
    Figure US20170117488A1-20170427-C00109
    Figure US20170117488A1-20170427-C00110
    Figure US20170117488A1-20170427-C00111
    Figure US20170117488A1-20170427-C00112
    Figure US20170117488A1-20170427-C00113
    Figure US20170117488A1-20170427-C00114
    Figure US20170117488A1-20170427-C00115
    Figure US20170117488A1-20170427-C00116
    Figure US20170117488A1-20170427-C00117
    Figure US20170117488A1-20170427-C00118
    Figure US20170117488A1-20170427-C00119
    Figure US20170117488A1-20170427-C00120
    Figure US20170117488A1-20170427-C00121
    Figure US20170117488A1-20170427-C00122
    Figure US20170117488A1-20170427-C00123
    Figure US20170117488A1-20170427-C00124
    Figure US20170117488A1-20170427-C00125
  • 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 US20170117488A1-20170427-C00126
    Figure US20170117488A1-20170427-C00127
    Figure US20170117488A1-20170427-C00128
    Figure US20170117488A1-20170427-C00129
    Figure US20170117488A1-20170427-C00130
    Figure US20170117488A1-20170427-C00131
    Figure US20170117488A1-20170427-C00132
    Figure US20170117488A1-20170427-C00133
    Figure US20170117488A1-20170427-C00134
    Figure US20170117488A1-20170427-C00135
    Figure US20170117488A1-20170427-C00136
    Figure US20170117488A1-20170427-C00137
    Figure US20170117488A1-20170427-C00138
    Figure US20170117488A1-20170427-C00139
    Figure US20170117488A1-20170427-C00140
    Figure US20170117488A1-20170427-C00141
    Figure US20170117488A1-20170427-C00142
    Figure US20170117488A1-20170427-C00143
    Figure US20170117488A1-20170427-C00144
    Figure US20170117488A1-20170427-C00145
    Figure US20170117488A1-20170427-C00146
    Figure US20170117488A1-20170427-C00147
    Figure US20170117488A1-20170427-C00148
    Figure US20170117488A1-20170427-C00149
    Figure US20170117488A1-20170427-C00150
    Figure US20170117488A1-20170427-C00151
    Figure US20170117488A1-20170427-C00152
    Figure US20170117488A1-20170427-C00153
    Figure US20170117488A1-20170427-C00154
    Figure US20170117488A1-20170427-C00155
    Figure US20170117488A1-20170427-C00156
    Figure US20170117488A1-20170427-C00157
    Figure US20170117488A1-20170427-C00158
    Figure US20170117488A1-20170427-C00159
    Figure US20170117488A1-20170427-C00160
    Figure US20170117488A1-20170427-C00161
    Figure US20170117488A1-20170427-C00162
    Figure US20170117488A1-20170427-C00163
    Figure US20170117488A1-20170427-C00164
    Figure US20170117488A1-20170427-C00165
    Figure US20170117488A1-20170427-C00166
    Figure US20170117488A1-20170427-C00167
    Figure US20170117488A1-20170427-C00168
    Figure US20170117488A1-20170427-C00169
    Figure US20170117488A1-20170427-C00170
    Figure US20170117488A1-20170427-C00171
    Figure US20170117488A1-20170427-C00172
    Figure US20170117488A1-20170427-C00173
    Figure US20170117488A1-20170427-C00174
    Figure US20170117488A1-20170427-C00175
    Figure US20170117488A1-20170427-C00176
    Figure US20170117488A1-20170427-C00177
    Figure US20170117488A1-20170427-C00178
    Figure US20170117488A1-20170427-C00179
    Figure US20170117488A1-20170427-C00180
    Figure US20170117488A1-20170427-C00181
    Figure US20170117488A1-20170427-C00182
    Figure US20170117488A1-20170427-C00183
    Figure US20170117488A1-20170427-C00184
    Figure US20170117488A1-20170427-C00185
    Figure US20170117488A1-20170427-C00186
    Figure US20170117488A1-20170427-C00187
    Figure US20170117488A1-20170427-C00188
    Figure US20170117488A1-20170427-C00189
    Figure US20170117488A1-20170427-C00190
    Figure US20170117488A1-20170427-C00191
    Figure US20170117488A1-20170427-C00192
    Figure US20170117488A1-20170427-C00193
    Figure US20170117488A1-20170427-C00194
    Figure US20170117488A1-20170427-C00195
    Figure US20170117488A1-20170427-C00196
    Figure US20170117488A1-20170427-C00197
    Figure US20170117488A1-20170427-C00198
    Figure US20170117488A1-20170427-C00199
    Figure US20170117488A1-20170427-C00200
    Figure US20170117488A1-20170427-C00201
    Figure US20170117488A1-20170427-C00202
    Figure US20170117488A1-20170427-C00203
    Figure US20170117488A1-20170427-C00204
    Figure US20170117488A1-20170427-C00205
    Figure US20170117488A1-20170427-C00206
    Figure US20170117488A1-20170427-C00207
    Figure US20170117488A1-20170427-C00208
    Figure US20170117488A1-20170427-C00209
  • Figure US20170117488A1-20170427-C00210
    Figure US20170117488A1-20170427-C00211
    Figure US20170117488A1-20170427-C00212
    Figure US20170117488A1-20170427-C00213
    Figure US20170117488A1-20170427-C00214
    Figure US20170117488A1-20170427-C00215
    Figure US20170117488A1-20170427-C00216
    Figure US20170117488A1-20170427-C00217
    Figure US20170117488A1-20170427-C00218
    Figure US20170117488A1-20170427-C00219
    Figure US20170117488A1-20170427-C00220
    Figure US20170117488A1-20170427-C00221
    Figure US20170117488A1-20170427-C00222
    Figure US20170117488A1-20170427-C00223
    Figure US20170117488A1-20170427-C00224
    Figure US20170117488A1-20170427-C00225
    Figure US20170117488A1-20170427-C00226
    Figure US20170117488A1-20170427-C00227
    Figure US20170117488A1-20170427-C00228
    Figure US20170117488A1-20170427-C00229
    Figure US20170117488A1-20170427-C00230
    Figure US20170117488A1-20170427-C00231
    Figure US20170117488A1-20170427-C00232
    Figure US20170117488A1-20170427-C00233
    Figure US20170117488A1-20170427-C00234
    Figure US20170117488A1-20170427-C00235
    Figure US20170117488A1-20170427-C00236
    Figure US20170117488A1-20170427-C00237
    Figure US20170117488A1-20170427-C00238
    Figure US20170117488A1-20170427-C00239
    Figure US20170117488A1-20170427-C00240
    Figure US20170117488A1-20170427-C00241
    Figure US20170117488A1-20170427-C00242
    Figure US20170117488A1-20170427-C00243
    Figure US20170117488A1-20170427-C00244
    Figure US20170117488A1-20170427-C00245
    Figure US20170117488A1-20170427-C00246
    Figure US20170117488A1-20170427-C00247
    Figure US20170117488A1-20170427-C00248
    Figure US20170117488A1-20170427-C00249
    Figure US20170117488A1-20170427-C00250
    Figure US20170117488A1-20170427-C00251
    Figure US20170117488A1-20170427-C00252
    Figure US20170117488A1-20170427-C00253
    Figure US20170117488A1-20170427-C00254
    Figure US20170117488A1-20170427-C00255
    Figure US20170117488A1-20170427-C00256
    Figure US20170117488A1-20170427-C00257
    Figure US20170117488A1-20170427-C00258
    Figure US20170117488A1-20170427-C00259
    Figure US20170117488A1-20170427-C00260
    Figure US20170117488A1-20170427-C00261
    Figure US20170117488A1-20170427-C00262
    Figure US20170117488A1-20170427-C00263
    Figure US20170117488A1-20170427-C00264
    Figure US20170117488A1-20170427-C00265
    Figure US20170117488A1-20170427-C00266
    Figure US20170117488A1-20170427-C00267
    Figure US20170117488A1-20170427-C00268
    Figure US20170117488A1-20170427-C00269
    Figure US20170117488A1-20170427-C00270
    Figure US20170117488A1-20170427-C00271
    Figure US20170117488A1-20170427-C00272
    Figure US20170117488A1-20170427-C00273
    Figure US20170117488A1-20170427-C00274
    Figure US20170117488A1-20170427-C00275
    Figure US20170117488A1-20170427-C00276
    Figure US20170117488A1-20170427-C00277
    Figure US20170117488A1-20170427-C00278
    Figure US20170117488A1-20170427-C00279
    Figure US20170117488A1-20170427-C00280
    Figure US20170117488A1-20170427-C00281
    Figure US20170117488A1-20170427-C00282
    Figure US20170117488A1-20170427-C00283
    Figure US20170117488A1-20170427-C00284
    Figure US20170117488A1-20170427-C00285
    Figure US20170117488A1-20170427-C00286
    Figure US20170117488A1-20170427-C00287
    Figure US20170117488A1-20170427-C00288
    Figure US20170117488A1-20170427-C00289
    Figure US20170117488A1-20170427-C00290
    Figure US20170117488A1-20170427-C00291
  • Figure US20170117488A1-20170427-C00292
    Figure US20170117488A1-20170427-C00293
    Figure US20170117488A1-20170427-C00294
    Figure US20170117488A1-20170427-C00295
    Figure US20170117488A1-20170427-C00296
    Figure US20170117488A1-20170427-C00297
    Figure US20170117488A1-20170427-C00298
    Figure US20170117488A1-20170427-C00299
    Figure US20170117488A1-20170427-C00300
    Figure US20170117488A1-20170427-C00301
    Figure US20170117488A1-20170427-C00302
    Figure US20170117488A1-20170427-C00303
    Figure US20170117488A1-20170427-C00304
    Figure US20170117488A1-20170427-C00305
    Figure US20170117488A1-20170427-C00306
    Figure US20170117488A1-20170427-C00307
    Figure US20170117488A1-20170427-C00308
    Figure US20170117488A1-20170427-C00309
    Figure US20170117488A1-20170427-C00310
    Figure US20170117488A1-20170427-C00311
    Figure US20170117488A1-20170427-C00312
    Figure US20170117488A1-20170427-C00313
    Figure US20170117488A1-20170427-C00314
    Figure US20170117488A1-20170427-C00315
    Figure US20170117488A1-20170427-C00316
    Figure US20170117488A1-20170427-C00317
    Figure US20170117488A1-20170427-C00318
    Figure US20170117488A1-20170427-C00319
    Figure US20170117488A1-20170427-C00320
    Figure US20170117488A1-20170427-C00321
    Figure US20170117488A1-20170427-C00322
    Figure US20170117488A1-20170427-C00323
    Figure US20170117488A1-20170427-C00324
    Figure US20170117488A1-20170427-C00325
    Figure US20170117488A1-20170427-C00326
    Figure US20170117488A1-20170427-C00327
    Figure US20170117488A1-20170427-C00328
    Figure US20170117488A1-20170427-C00329
    Figure US20170117488A1-20170427-C00330
    Figure US20170117488A1-20170427-C00331
    Figure US20170117488A1-20170427-C00332
    Figure US20170117488A1-20170427-C00333
    Figure US20170117488A1-20170427-C00334
    Figure US20170117488A1-20170427-C00335
    Figure US20170117488A1-20170427-C00336
    Figure US20170117488A1-20170427-C00337
    Figure US20170117488A1-20170427-C00338
    Figure US20170117488A1-20170427-C00339
    Figure US20170117488A1-20170427-C00340
    Figure US20170117488A1-20170427-C00341
    Figure US20170117488A1-20170427-C00342
    Figure US20170117488A1-20170427-C00343
    Figure US20170117488A1-20170427-C00344
  • 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 US20170117488A1-20170427-C00345
  • wherein
  • L is selected from the following structures:
  • Figure US20170117488A1-20170427-C00346
  • 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 US20170117488A1-20170427-C00347
    Figure US20170117488A1-20170427-C00348
    Figure US20170117488A1-20170427-C00349
    Figure US20170117488A1-20170427-C00350
    Figure US20170117488A1-20170427-C00351
    Figure US20170117488A1-20170427-C00352
    Figure US20170117488A1-20170427-C00353
    Figure US20170117488A1-20170427-C00354
    Figure US20170117488A1-20170427-C00355
    Figure US20170117488A1-20170427-C00356
    Figure US20170117488A1-20170427-C00357
    Figure US20170117488A1-20170427-C00358
    Figure US20170117488A1-20170427-C00359
    Figure US20170117488A1-20170427-C00360
    Figure US20170117488A1-20170427-C00361
    Figure US20170117488A1-20170427-C00362
    Figure US20170117488A1-20170427-C00363
    Figure US20170117488A1-20170427-C00364
    Figure US20170117488A1-20170427-C00365
    Figure US20170117488A1-20170427-C00366
    Figure US20170117488A1-20170427-C00367
    Figure US20170117488A1-20170427-C00368
    Figure US20170117488A1-20170427-C00369
    Figure US20170117488A1-20170427-C00370
    Figure US20170117488A1-20170427-C00371
    Figure US20170117488A1-20170427-C00372
    Figure US20170117488A1-20170427-C00373
    Figure US20170117488A1-20170427-C00374
    Figure US20170117488A1-20170427-C00375
    Figure US20170117488A1-20170427-C00376
    Figure US20170117488A1-20170427-C00377
    Figure US20170117488A1-20170427-C00378
    Figure US20170117488A1-20170427-C00379
    Figure US20170117488A1-20170427-C00380
    Figure US20170117488A1-20170427-C00381
    Figure US20170117488A1-20170427-C00382
    Figure US20170117488A1-20170427-C00383
    Figure US20170117488A1-20170427-C00384
    Figure US20170117488A1-20170427-C00385
    Figure US20170117488A1-20170427-C00386
    Figure US20170117488A1-20170427-C00387
    Figure US20170117488A1-20170427-C00388
    Figure US20170117488A1-20170427-C00389
    Figure US20170117488A1-20170427-C00390
    Figure US20170117488A1-20170427-C00391
    Figure US20170117488A1-20170427-C00392
    Figure US20170117488A1-20170427-C00393
    Figure US20170117488A1-20170427-C00394
    Figure US20170117488A1-20170427-C00395
    Figure US20170117488A1-20170427-C00396
    Figure US20170117488A1-20170427-C00397
    Figure US20170117488A1-20170427-C00398
  • 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 n/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 1,000 nit, luminescent efficiency, CIE color coordinate, and the lifespan taken to be reduced from 100% to 90% of the constant current at a luminance of 5,000 nit as provided in Table 1 below.
  • Figure US20170117488A1-20170427-C00399
    Figure US20170117488A1-20170427-C00400
    • 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
    Hole Color T90
    Transport Voltage Efficiency Coordinate lifespan
    Layer Host Dopant (V) (cd/A) (x, y) (hr)
    Device Example HT- H1-1:H2-2 D-96 4.3 25.5 0.663, 0.336 360
    1-1 1/HT-2
    Comparative HT- H2-2 D-96 4.1 28.2 0.662, 0.337 100
    Example 1-1 1/HT-2
    • 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 15 wt % 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 15,000 nit 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 15,000 nit 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
    Hole Color T90
    Transport Voltage Efficiency Coordinate lifespan
    Layer Host Dopant [V] [cd/A] (x, y) [hr]
    Device HT-1 H1-1:H2-25 D-25 3.3 43.2 0.297, 100
    Example 2-1 0.660
    Device HT-1 H1-1:H2-31 D-25 3 58.8 0.303, 143
    Example 2-2 0.657
    Device HT-1 H1-1:H2-48 D-25 2.8 55.3 0.302, 124
    Example 2-3 0.657
    Device HT-1 H1-1:H2-34 D-25 3 55.7 0.302, 127
    Example 2-4 0.657
    Device HT-1 H1-11:H2- D-25 2.9 56.9 0.306, 147
    Example 2-5 31 0.656
    Device HT-1 H1-12:H2- D-25 2.9 54.5 0.304, 206
    Example 2-6 31 0.657
    Device HT-1 H1-14:H2- D-25 3.1 49.1 0.306, 124
    Example 2-7 31 0.655
    Device HT-1 H1-4:H2-31 D-25 2.9 55.2 0.300, 131
    Example 2-8 0.657
    Device HT-1 H1-35:H2- D-25 2.9 55.6 0.303, 161
    Example 2-9 31 0.656
    Device HT-1 H1-1:H2- D-25 3 55.6 0.303, 124
    Example 101 0.656
    2-10
    Device HT-1 H1-9:H2-31 D-25 2.9 56 0.301, 203
    Example 0.657
    2-11
    Device HT-1 H1-2:H2-31 D-25 2.8 54.9 0.307, 116
    Example 2- 0.656
    12
    Device HT-1 H1-34:H2- D-25 3 52.5 0.303, 160
    Example 31 0.657
    2-13
    Device HT-1 H1-1:H2-31 D-1 2.8 57.8 0.315, 254
    Example 0.658
    2-14
    Device HT-1 H1-1:H2-48 D-1 2.8 60.2 0.316, 240
    Example 0.659
    2-15
    Device HT-1 H1-11:H2- D-1 2.8 52.4 0.317, 274
    Example 31 0.658
    2-16
    Device HT-1 H1-11:H2- D-1 2.7 54.3 0.316, 272
    Example 48 0.659
    2-17
    Device HT-1 H1-11:H2- D-1 2.9 51.9 0.319, 240
    Example 87 0.655
    2-18
    Device HT- H1-1:H2-30 D-136 3.3 63.9 0.324, 240
    Example 3-1 1/HT-3 0.660
    Device HT- H1-1:H2-31 D-136 3.2 71.2 0.326, 265
    Example 3-2 1/HT-3 0.659
    Device HT- H1-1:H2-48 D-136 3.1 68 0.325, 265
    Example 3-3 1/HT-3 0.659
    Device HT- H1-1:H2-87 D-136 3.3 67.4 0.327, 290
    Example 3-4 1/HT-3 0.658
    Device HT- H1-11:H2- D-136 3.1 69.2 0.327, 292
    Example 3-5 1/HT-3 31 0.658
    Device HT- H1-11:H2- D-136 3.2 64 0.326, 322
    Example 3-6 1/HT-3 48 0.658
    Device HT- H1-11:H2- D-136 3.1 65.2 0.327, 367
    Example 3-7 1/HT-3 87 0.657
    Device HT- H1-35:H2- D-136 3.1 65.2 0.330, 408
    Example 3-8 1/HT-3 125 0.655
    Device HT- H1-35:H2- D-164 3.2 61.5 0.316, 241
    Example 3-9 1/HT-3 31 0.656
    Device HT- H1-1:H2-31 D-168 3.2 62.1 0.281, 148
    Example 1/HT-3 0.665
    3-10
    Device HT- H1-35:H2- D-168 3.2 59.4 0.278, 162
    Example 1/HT-3 31 0.668
    3-11
    Device HT- H1-12:H2- D-168 3.1 56.6 0.288, 164
    Example 1/HT-3 125 0.665
    3-12
    Device HT- H1-12:H2- D-180 3.1 49.7 0.291, 240
    Example 1/HT-3 125 0.664
    3-13
    Comparative HT-1 H1-12 D-25 5.9 3.1 0.299, x
    Example 0.656
    2-1
    Comparative HT-1 H1-4 D-25 6.7 3 0.289, x
    Example 0.658
    2-2
    Comparative HT-1 H1-35 D-25 6.6 3.9 0.395, x
    Example 0.658
    2-3
    Comparative HT-1 H2-25 D-25 3.1 54.2 0.308, 45
    Example 0.655
    3-1
    Comparative HT-1 H2-31 D-25 2.9 42.8 0.314, 39
    Example 0.652
    3-2
    Comparative HT-1 H2-48 D-25 2.6 49.6 0.314, 67
    Example 0.652
    3-3
    Comparative HT-1 H2-101 D-25 2.8 50.3 0.315, 24
    Example 0.651
    3-4
    Comparative HT-1 H2-34 D-25 2.7 49.2 0.312, 38
    Example 0.652
    3-5
    Comparative HT-1 H2-30 D-25 2.8 55.3 0.314, 70
    Example 0.652
    3-6
    Comparative HT-1 H2-31 D-1 2.9 33.5 0.323, 130
    Example 0.653
    3-7
    Comparative HT-1 H2-48 D-1 2.6 41.2 0.325, 124
    Example 0.653
    3-8
    Comparative HT-1 H2-87 D-1 2.8 37.9 0.323, 146
    Example 0.653
    3-9
    Comparative HT- H2-125 D-136 3.0 64.9 0.337, 124
    Example 1/HT-3 0.649
    4-1
    • 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 5,000 nit as provided in Table 3 below.
  • Figure US20170117488A1-20170427-C00401
    • 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
    Hole Color
    Transport Voltage Efficiency Coordinate T95 lifespan
    Layer Host Dopant [V] [cd/A] (x, y) [hr]
    Device HT-1/ H1-287:H2-496 D-96 3.8 30.8 0.667, 310
    Example HT-4 0.333
    4-1
    Device HT-1/ H1-12:H2-504 D-96 3.5 30.7 0.667, 390
    Example HT-4 0.333
    4-2
    Device HT-1/ H1-9:H2-496 D-96 3.9 31.1 0.665, 130
    Example HT-4 0.335
    4-3
    Device HT-1/ H1-35:H2-496 D-96 3.8 31.1 0.665, 200
    Example 4-4 HT-4 0.334
    Device HT-1/ H1-287:H2-504 D-96 3.7 31.3 0.666, 200
    Example 4-5 HT-4 0.333
    Device HT-1/ H1-282:H2-504 D-96 3.7 31.4 0.666, 120
    Example 4-6 HT-4 0.334
    Device HT-1/ H1-12:H2-496 D-96 3.6 29.2 0.667, 150
    Example 4-7 HT-4 0.333
    Comparative HT-1/ H2-496 D-96 3.7 31.0 0.665, 90
    Example 5-1 HT-4 0.334
    Comparative HT-1/ H2-504 D-96 3.7 31 0.667, 70
    Example 5-2 HT-4 0.333
    • 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 15,000 nit 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
    Hole Color T97
    Transport Voltage Efficiency Coordinate lifespan
    Layer Host Dopant [V] [cd/A] (x, y) [hr]
    Device HT-1/HT-3 H1-12: D-134 3.1 63.2 0.313, 39
    Example H2-660 0.665
    5-1
    Device HT-1/HT-3 H1-35: D-134 3.2 64.8 0.312, 56
    Example H2-660 0.665
    5-2
    Comparative HT-1/HT-3 H1-12 D-134 6.4 2.9 0.305, x
    Example 0.660
    6-1
    Comparative HT-1/HT-3 H1-35 D-134 7.2 3.5 0.302, x
    Example 0.664
    6-2
    Comparative HT-1/HT-3 H2-660 D-134 3.0 55.4 0.321,  5
    Example 0.659
    7-1
  • 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 US20170117488A1-20170427-C00402
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 US20170117488A1-20170427-C00403
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 US20170117488A1-20170427-C00404
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 US20170117488A1-20170427-C00405
Figure US20170117488A1-20170427-C00406
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 US20170117488A1-20170427-C00407
Figure US20170117488A1-20170427-C00408
Figure US20170117488A1-20170427-C00409
Figure US20170117488A1-20170427-C00410
Figure US20170117488A1-20170427-C00411
Figure US20170117488A1-20170427-C00412
Figure US20170117488A1-20170427-C00413
Figure US20170117488A1-20170427-C00414
Figure US20170117488A1-20170427-C00415
Figure US20170117488A1-20170427-C00416
Figure US20170117488A1-20170427-C00417
Figure US20170117488A1-20170427-C00418
Figure US20170117488A1-20170427-C00419
Figure US20170117488A1-20170427-C00420
Figure US20170117488A1-20170427-C00421
Figure US20170117488A1-20170427-C00422
Figure US20170117488A1-20170427-C00423
Figure US20170117488A1-20170427-C00424
Figure US20170117488A1-20170427-C00425
Figure US20170117488A1-20170427-C00426
Figure US20170117488A1-20170427-C00427
Figure US20170117488A1-20170427-C00428
Figure US20170117488A1-20170427-C00429
Figure US20170117488A1-20170427-C00430
Figure US20170117488A1-20170427-C00431
Figure US20170117488A1-20170427-C00432
Figure US20170117488A1-20170427-C00433
Figure US20170117488A1-20170427-C00434
Figure US20170117488A1-20170427-C00435
Figure US20170117488A1-20170427-C00436
Figure US20170117488A1-20170427-C00437
Figure US20170117488A1-20170427-C00438
Figure US20170117488A1-20170427-C00439
Figure US20170117488A1-20170427-C00440
Figure US20170117488A1-20170427-C00441
Figure US20170117488A1-20170427-C00442
Figure US20170117488A1-20170427-C00443
Figure US20170117488A1-20170427-C00444
Figure US20170117488A1-20170427-C00445
Figure US20170117488A1-20170427-C00446
Figure US20170117488A1-20170427-C00447
Figure US20170117488A1-20170427-C00448
Figure US20170117488A1-20170427-C00449
Figure US20170117488A1-20170427-C00450
Figure US20170117488A1-20170427-C00451
Figure US20170117488A1-20170427-C00452
Figure US20170117488A1-20170427-C00453
Figure US20170117488A1-20170427-C00454
Figure US20170117488A1-20170427-C00455
Figure US20170117488A1-20170427-C00456
Figure US20170117488A1-20170427-C00457
Figure US20170117488A1-20170427-C00458
Figure US20170117488A1-20170427-C00459
Figure US20170117488A1-20170427-C00460
Figure US20170117488A1-20170427-C00461
Figure US20170117488A1-20170427-C00462
Figure US20170117488A1-20170427-C00463
Figure US20170117488A1-20170427-C00464
Figure US20170117488A1-20170427-C00465
Figure US20170117488A1-20170427-C00466
Figure US20170117488A1-20170427-C00467
Figure US20170117488A1-20170427-C00468
Figure US20170117488A1-20170427-C00469
Figure US20170117488A1-20170427-C00470
Figure US20170117488A1-20170427-C00471
Figure US20170117488A1-20170427-C00472
Figure US20170117488A1-20170427-C00473
Figure US20170117488A1-20170427-C00474
Figure US20170117488A1-20170427-C00475
Figure US20170117488A1-20170427-C00476
Figure US20170117488A1-20170427-C00477
Figure US20170117488A1-20170427-C00478
Figure US20170117488A1-20170427-C00479
Figure US20170117488A1-20170427-C00480
Figure US20170117488A1-20170427-C00481
Figure US20170117488A1-20170427-C00482
Figure US20170117488A1-20170427-C00483
Figure US20170117488A1-20170427-C00484
Figure US20170117488A1-20170427-C00485
Figure US20170117488A1-20170427-C00486
Figure US20170117488A1-20170427-C00487
Figure US20170117488A1-20170427-C00488
Figure US20170117488A1-20170427-C00489
Figure US20170117488A1-20170427-C00490
Figure US20170117488A1-20170427-C00491
Figure US20170117488A1-20170427-C00492
Figure US20170117488A1-20170427-C00493
Figure US20170117488A1-20170427-C00494
Figure US20170117488A1-20170427-C00495
Figure US20170117488A1-20170427-C00496
Figure US20170117488A1-20170427-C00497
Figure US20170117488A1-20170427-C00498
Figure US20170117488A1-20170427-C00499
Figure US20170117488A1-20170427-C00500
Figure US20170117488A1-20170427-C00501
Figure US20170117488A1-20170427-C00502
Figure US20170117488A1-20170427-C00503
Figure US20170117488A1-20170427-C00504
Figure US20170117488A1-20170427-C00505
Figure US20170117488A1-20170427-C00506
Figure US20170117488A1-20170427-C00507
Figure US20170117488A1-20170427-C00508
Figure US20170117488A1-20170427-C00509
Figure US20170117488A1-20170427-C00510
Figure US20170117488A1-20170427-C00511
Figure US20170117488A1-20170427-C00512
Figure US20170117488A1-20170427-C00513
Figure US20170117488A1-20170427-C00514
Figure US20170117488A1-20170427-C00515
Figure US20170117488A1-20170427-C00516
Figure US20170117488A1-20170427-C00517
Figure US20170117488A1-20170427-C00518
Figure US20170117488A1-20170427-C00519
Figure US20170117488A1-20170427-C00520
Figure US20170117488A1-20170427-C00521
Figure US20170117488A1-20170427-C00522
Figure US20170117488A1-20170427-C00523
Figure US20170117488A1-20170427-C00524
Figure US20170117488A1-20170427-C00525
Figure US20170117488A1-20170427-C00526
Figure US20170117488A1-20170427-C00527
Figure US20170117488A1-20170427-C00528
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 US20170117488A1-20170427-C00529
Figure US20170117488A1-20170427-C00530
Figure US20170117488A1-20170427-C00531
Figure US20170117488A1-20170427-C00532
Figure US20170117488A1-20170427-C00533
Figure US20170117488A1-20170427-C00534
Figure US20170117488A1-20170427-C00535
Figure US20170117488A1-20170427-C00536
Figure US20170117488A1-20170427-C00537
Figure US20170117488A1-20170427-C00538
Figure US20170117488A1-20170427-C00539
Figure US20170117488A1-20170427-C00540
Figure US20170117488A1-20170427-C00541
Figure US20170117488A1-20170427-C00542
Figure US20170117488A1-20170427-C00543
Figure US20170117488A1-20170427-C00544
Figure US20170117488A1-20170427-C00545
Figure US20170117488A1-20170427-C00546
Figure US20170117488A1-20170427-C00547
Figure US20170117488A1-20170427-C00548
Figure US20170117488A1-20170427-C00549
Figure US20170117488A1-20170427-C00550
Figure US20170117488A1-20170427-C00551
Figure US20170117488A1-20170427-C00552
Figure US20170117488A1-20170427-C00553
Figure US20170117488A1-20170427-C00554
Figure US20170117488A1-20170427-C00555
Figure US20170117488A1-20170427-C00556
Figure US20170117488A1-20170427-C00557
Figure US20170117488A1-20170427-C00558
Figure US20170117488A1-20170427-C00559
Figure US20170117488A1-20170427-C00560
Figure US20170117488A1-20170427-C00561
Figure US20170117488A1-20170427-C00562
Figure US20170117488A1-20170427-C00563
Figure US20170117488A1-20170427-C00564
Figure US20170117488A1-20170427-C00565
Figure US20170117488A1-20170427-C00566
Figure US20170117488A1-20170427-C00567
Figure US20170117488A1-20170427-C00568
Figure US20170117488A1-20170427-C00569
Figure US20170117488A1-20170427-C00570
Figure US20170117488A1-20170427-C00571
Figure US20170117488A1-20170427-C00572
Figure US20170117488A1-20170427-C00573
Figure US20170117488A1-20170427-C00574
Figure US20170117488A1-20170427-C00575
Figure US20170117488A1-20170427-C00576
Figure US20170117488A1-20170427-C00577
Figure US20170117488A1-20170427-C00578
Figure US20170117488A1-20170427-C00579
Figure US20170117488A1-20170427-C00580
Figure US20170117488A1-20170427-C00581
Figure US20170117488A1-20170427-C00582
Figure US20170117488A1-20170427-C00583
Figure US20170117488A1-20170427-C00584
Figure US20170117488A1-20170427-C00585
Figure US20170117488A1-20170427-C00586
Figure US20170117488A1-20170427-C00587
Figure US20170117488A1-20170427-C00588
Figure US20170117488A1-20170427-C00589
Figure US20170117488A1-20170427-C00590
Figure US20170117488A1-20170427-C00591
Figure US20170117488A1-20170427-C00592
Figure US20170117488A1-20170427-C00593
Figure US20170117488A1-20170427-C00594
Figure US20170117488A1-20170427-C00595
Figure US20170117488A1-20170427-C00596
Figure US20170117488A1-20170427-C00597
Figure US20170117488A1-20170427-C00598
Figure US20170117488A1-20170427-C00599
Figure US20170117488A1-20170427-C00600
Figure US20170117488A1-20170427-C00601
Figure US20170117488A1-20170427-C00602
Figure US20170117488A1-20170427-C00603
Figure US20170117488A1-20170427-C00604
Figure US20170117488A1-20170427-C00605
Figure US20170117488A1-20170427-C00606
Figure US20170117488A1-20170427-C00607
Figure US20170117488A1-20170427-C00608
Figure US20170117488A1-20170427-C00609
Figure US20170117488A1-20170427-C00610
Figure US20170117488A1-20170427-C00611
Figure US20170117488A1-20170427-C00612
Figure US20170117488A1-20170427-C00613
Figure US20170117488A1-20170427-C00614
Figure US20170117488A1-20170427-C00615
Figure US20170117488A1-20170427-C00616
Figure US20170117488A1-20170427-C00617
Figure US20170117488A1-20170427-C00618
Figure US20170117488A1-20170427-C00619
Figure US20170117488A1-20170427-C00620
Figure US20170117488A1-20170427-C00621
Figure US20170117488A1-20170427-C00622
Figure US20170117488A1-20170427-C00623
Figure US20170117488A1-20170427-C00624
Figure US20170117488A1-20170427-C00625
Figure US20170117488A1-20170427-C00626
Figure US20170117488A1-20170427-C00627
Figure US20170117488A1-20170427-C00628
Figure US20170117488A1-20170427-C00629
Figure US20170117488A1-20170427-C00630
Figure US20170117488A1-20170427-C00631
Figure US20170117488A1-20170427-C00632
Figure US20170117488A1-20170427-C00633
Figure US20170117488A1-20170427-C00634
Figure US20170117488A1-20170427-C00635
Figure US20170117488A1-20170427-C00636
Figure US20170117488A1-20170427-C00637
Figure US20170117488A1-20170427-C00638
Figure US20170117488A1-20170427-C00639
Figure US20170117488A1-20170427-C00640
Figure US20170117488A1-20170427-C00641
Figure US20170117488A1-20170427-C00642
Figure US20170117488A1-20170427-C00643
Figure US20170117488A1-20170427-C00644
Figure US20170117488A1-20170427-C00645
Figure US20170117488A1-20170427-C00646
Figure US20170117488A1-20170427-C00647
Figure US20170117488A1-20170427-C00648
Figure US20170117488A1-20170427-C00649
Figure US20170117488A1-20170427-C00650
Figure US20170117488A1-20170427-C00651
Figure US20170117488A1-20170427-C00652
Figure US20170117488A1-20170427-C00653
Figure US20170117488A1-20170427-C00654
Figure US20170117488A1-20170427-C00655
Figure US20170117488A1-20170427-C00656
Figure US20170117488A1-20170427-C00657
Figure US20170117488A1-20170427-C00658
Figure US20170117488A1-20170427-C00659
Figure US20170117488A1-20170427-C00660
Figure US20170117488A1-20170427-C00661
Figure US20170117488A1-20170427-C00662
Figure US20170117488A1-20170427-C00663
Figure US20170117488A1-20170427-C00664
Figure US20170117488A1-20170427-C00665
Figure US20170117488A1-20170427-C00666
Figure US20170117488A1-20170427-C00667
Figure US20170117488A1-20170427-C00668
Figure US20170117488A1-20170427-C00669
Figure US20170117488A1-20170427-C00670
Figure US20170117488A1-20170427-C00671
Figure US20170117488A1-20170427-C00672
Figure US20170117488A1-20170427-C00673
Figure US20170117488A1-20170427-C00674
Figure US20170117488A1-20170427-C00675
Figure US20170117488A1-20170427-C00676
Figure US20170117488A1-20170427-C00677
Figure US20170117488A1-20170427-C00678
Figure US20170117488A1-20170427-C00679
Figure US20170117488A1-20170427-C00680
Figure US20170117488A1-20170427-C00681
Figure US20170117488A1-20170427-C00682
Figure US20170117488A1-20170427-C00683
Figure US20170117488A1-20170427-C00684
Figure US20170117488A1-20170427-C00685
Figure US20170117488A1-20170427-C00686
Figure US20170117488A1-20170427-C00687
Figure US20170117488A1-20170427-C00688
Figure US20170117488A1-20170427-C00689
Figure US20170117488A1-20170427-C00690
Figure US20170117488A1-20170427-C00691
Figure US20170117488A1-20170427-C00692
Figure US20170117488A1-20170427-C00693
Figure US20170117488A1-20170427-C00694
Figure US20170117488A1-20170427-C00695
Figure US20170117488A1-20170427-C00696
Figure US20170117488A1-20170427-C00697
Figure US20170117488A1-20170427-C00698
Figure US20170117488A1-20170427-C00699
Figure US20170117488A1-20170427-C00700
Figure US20170117488A1-20170427-C00701
Figure US20170117488A1-20170427-C00702
Figure US20170117488A1-20170427-C00703
Figure US20170117488A1-20170427-C00704
Figure US20170117488A1-20170427-C00705
Figure US20170117488A1-20170427-C00706
Figure US20170117488A1-20170427-C00707
Figure US20170117488A1-20170427-C00708
Figure US20170117488A1-20170427-C00709
Figure US20170117488A1-20170427-C00710
Figure US20170117488A1-20170427-C00711
Figure US20170117488A1-20170427-C00712
Figure US20170117488A1-20170427-C00713
Figure US20170117488A1-20170427-C00714
Figure US20170117488A1-20170427-C00715
Figure US20170117488A1-20170427-C00716
Figure US20170117488A1-20170427-C00717
Figure US20170117488A1-20170427-C00718
Figure US20170117488A1-20170427-C00719
Figure US20170117488A1-20170427-C00720
Figure US20170117488A1-20170427-C00721
Figure US20170117488A1-20170427-C00722
Figure US20170117488A1-20170427-C00723
Figure US20170117488A1-20170427-C00724
Figure US20170117488A1-20170427-C00725
Figure US20170117488A1-20170427-C00726
Figure US20170117488A1-20170427-C00727
Figure US20170117488A1-20170427-C00728
Figure US20170117488A1-20170427-C00729
Figure US20170117488A1-20170427-C00730
Figure US20170117488A1-20170427-C00731
Figure US20170117488A1-20170427-C00732
Figure US20170117488A1-20170427-C00733
Figure US20170117488A1-20170427-C00734
Figure US20170117488A1-20170427-C00735
Figure US20170117488A1-20170427-C00736
Figure US20170117488A1-20170427-C00737
Figure US20170117488A1-20170427-C00738
Figure US20170117488A1-20170427-C00739
Figure US20170117488A1-20170427-C00740
Figure US20170117488A1-20170427-C00741
Figure US20170117488A1-20170427-C00742
Figure US20170117488A1-20170427-C00743
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Figure US20170117488A1-20170427-C00745
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Figure US20170117488A1-20170427-C00747
Figure US20170117488A1-20170427-C00748
Figure US20170117488A1-20170427-C00749
Figure US20170117488A1-20170427-C00750
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