US20080079354A1 - Quinoxaline Derivative, And Light Emitting Element, Light Emitting Device, And Electronic Device Using the Quinoxaline Derivative - Google Patents

Quinoxaline Derivative, And Light Emitting Element, Light Emitting Device, And Electronic Device Using the Quinoxaline Derivative Download PDF

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US20080079354A1
US20080079354A1 US11/859,422 US85942207A US2008079354A1 US 20080079354 A1 US20080079354 A1 US 20080079354A1 US 85942207 A US85942207 A US 85942207A US 2008079354 A1 US2008079354 A1 US 2008079354A1
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light emitting
emitting element
quinoxaline derivative
emitting layer
electrodes
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Masakazu Egawa
Satoshi Seo
Nobuharu Ohsawa
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Semiconductor Energy Laboratory Co Ltd
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Semiconductor Energy Laboratory Co Ltd
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Assigned to SEMICONDUCTOR ENERGY LABORATORY CO., LTD. reassignment SEMICONDUCTOR ENERGY LABORATORY CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: OHSAWA, NOBUHARU, SEO, SATOSHI, EGAWA, MASAKAZU
Publication of US20080079354A1 publication Critical patent/US20080079354A1/en
Priority to US13/459,981 priority Critical patent/US8703305B2/en
Priority to US14/257,241 priority patent/US9062036B2/en
Priority to US14/746,187 priority patent/US9328098B2/en
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    • H10K85/30—Coordination compounds
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    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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Definitions

  • the present invention relates to a quinoxaline derivative, and a light emitting element, a light emitting device, and an electronic device each of which uses the quinoxaline derivative.
  • An organic compound has various material systems compared with an inorganic compound, and has possibility to synthesize materials having various functions depending on the molecular design. Owing to these advantages, photo electronics and electronics which use a functional organic material have been attracting attention in recent years.
  • a solar cell, a light emitting element, an organic transistor, and the like can be given as examples of an electronic device using an organic compound as a functional organic material. These are devices that take advantage of electric properties and optical properties of the organic compound. Of these, a light emitting element has, in particular, shown remarkable development.
  • a light emission mechanism of a light emitting element is as follows: by applying a voltage between a pair of electrodes which interpose a light emitting layer, electrons injected from a cathode and holes injected from an anode are recombined in the luminescent center of the light emitting layer so as to form molecular excitons, and energy is released to emit light when the molecular excitons return to a ground state.
  • excitation states a singlet excitation state and a triplet excitation state are known, and it is thought that light emission can be obtained through either of these excitation states.
  • Such a light emitting element has a lot of problems depending on its material in the case where an element property thereof is improved.
  • improvement of element structure, development of materials, and the like have been carried out.
  • Non-Patent Document 1 C. W. Tang and one other, Applied Physics Letters, vol. 51, No. 12, 913-915 (1987)).
  • Non-Patent Document 1 By applying a voltage to the light emitting element described in Non-Patent Document 1, light emission can be obtained from an organic compound having a light emitting property and an electron transporting property.
  • Non-Patent Document 1 functional separation is carried out; that is, a hole transporting layer transports holes, and an electron transporting layer transports electrons and emits light.
  • various interactions e.g., formation of exciplexes
  • a change in the light emission spectrum or a decline in light emission efficiency may occur.
  • Non-Patent Document 2 Chihaya Adachi and three others, Japanese Journal of Applied Physics, vol. 27, No. 2, L269-L271 (1988)).
  • the light emitting layer is preferably formed by using a bipolar organic compound which has both an electron transporting property and a hole transporting property, in order to further suppress the interaction occurring at the interface.
  • organic compounds are, however, monopolar materials in which either a hole transporting property or an electron transporting property is more pronounced than the other one.
  • Patent Document 1 PCT International Publication No. 2004/094389
  • a bipolar quinoxaline derivative has been described.
  • characteristics such as heat resistance are not high enough yet, development of more varied bipolar organic compounds has been required.
  • an object of the present invention is to provide a new bipolar organic compound.
  • an object of the present invention is to provide a bipolar organic compound having excellent heat resistance and to provide a bipolar organic compound which is electrochemically stable.
  • another object is to provide a light emitting element and a light emitting device of which a driving voltage and power consumption are reduced by using the bipolar organic compound of the present invention. Further, another object is to provide a light emitting element and a light emitting device which have excellent heat resistance by using the bipolar organic compound of the present invention. Further, another object is to provide a light emitting element and a light emitting device which have a long life by using the bipolar organic compound of the present invention.
  • Still another object is to provide an electronic device in which power consumption is reduced by using the bipolar organic compound of the present invention. Further, another object is to provide an electronic device having excellent heat resistance. Further, another object is to provide a long-life electronic device.
  • One mode of the present invention is a quinoxaline derivative represented by the general formula (1).
  • R 1 to R 4 may be the same or different and each represent any one of a hydrogen atom, an alkyl group of carbon number 1 to 4, and an aryl group of carbon number 6 to 25.
  • R 1 , R 2 , and R 3 may bond to R 2 , R 3 , and R 4 , respectively, to form a condensed ring.
  • Ar 1 represents an arylene group of carbon number 6 to 25.
  • Ar 2 and Ar 3 may be the same or different and each represent an arylene group of carbon number 6 to 25.
  • Ar 1 and Ar 2 may bond to Ar 2 and Ar 3 , respectively.
  • Another mode of the present invention is a quinoxaline derivative represented by the general formula (2).
  • R 5 to R 18 may be the same or different and each represent any one of a hydrogen atom, an alkyl group of carbon number 1 to 4, and an aryl group of carbon number 6 to 15.8 R 5 , R 6 , R 7 , R 8 , R 10 , R 11 , R 12 , R 13 , R 15 , and R 17 may bond to R 6 , R 7 , R 8 , R 9 , R 11 , R 12 , R 13 , R 14 , R 16 , and R 18 , respectively, to form a condensed ring.
  • Another mode of the present invention is a quinoxaline derivative represented by the general formula (3).
  • R 19 to R 24 may be the same or different and each represent any one of a hydrogen atom, an alkyl group of carbon number 1 to 4, and an aryl group of car bon number 6 to 15.
  • R 19 , R 20 , R 21 , and R 22 may bond to R 20 , R 21 , R 22 , and R 23 , respectively, to form a condensed ring.
  • Another mode of the present invention is a quinoxaline derivative represented by the general formula (4).
  • R 25 to R 30 may be the same or different and each represent any one of a hydrogen atom, an alkyl group of carbon number 1 to 4, and an aryl group of carbon number 6 to 15.
  • R 25 and R 27 may bond to R 26 and R 28 , respectively, to form a condensed ring.
  • Another mode of the present invention is a quinoxaline derivative represented by the structural formula (11).
  • Another mode of the present invention is a quinoxaline derivative represented by the structural formula (12).
  • Another mode of the present invention is a quinoxaline derivative represented by the structural formula (13).
  • Another mode of the present invention is a light emitting element using the aforementioned quinoxaline derivative; specifically, a light emitting element in which the aforementioned quinoxaline derivative is provided between a pair of electrodes.
  • Another mode of the present invention is a light emitting element in which a light emitting layer is provided between a pair of electrodes and the light emitting layer contains the aforementioned quinoxaline derivative.
  • Another mode of the present invention is a light emitting element in which a light emitting layer is provided between a pair of electrodes and the light emitting layer contains the aforementioned quinoxaline derivative and a fluorescent material.
  • Another mode of the present invention is a light emitting element in which a light emitting layer is provided between a pair of electrodes and the light emitting layer contains the quinoxaline derivative and a phosphorescent material.
  • a light emission spectrum of the phosphorescent material have a peak at 560 nm to 700 nm (both inclusive).
  • the light emitting device of the present invention includes: between a pair of electrodes, a light emitting element containing the above-described quinoxaline derivative and a control means for controlling light emission of the light emitting element.
  • a “light emitting device” in this specification includes in its category, an image displaying device, a light emitting device, or a light source (including a lighting device).
  • a connector such as an FPC (Flexible Printed Circuit), a TAB (Tape Automated Bonding) tape, or a TCP (Tape Carrier Package) is attached to a panel
  • a module in which a printed wiring board is mounted on the tip of a TAB tape or a TCP and a module in which an IC (integrated circuit) is directly mounted on a light emitting element by COG (Chip On Glass).
  • COG Chip On Glass
  • the electronic device of the present invention includes a display portion provided with the aforementioned light emitting element and control means for controlling light emission of the light emitting element.
  • the quinoxaline derivative of the present invention is bipolar and excellent in both electron transporting property and hole transporting property. Further, the quinoxaline derivative of the present invention has a high glass transition point and excellent heat resistance. Further, the quinoxaline derivative of the present invention is stable with respect to electrochemical oxidation or reduction.
  • the quinoxaline derivative of the present invention which is bipolar, a light emitting element and a light emitting device in which a driving voltage is low and power consumption is low can be obtained.
  • the quinoxaline derivative of the present invention which has a high glass transition point, a light emitting element and a light emitting device which have high heat resistance can be obtained.
  • the quinoxaline derivative of the present invention which is stable with respect to electrochemical oxidation or reduction, a long-life light emitting element and a long-life light emitting device can be obtained.
  • the quinoxaline derivative of the present invention by using the quinoxaline derivative of the present invention, an electronic device in which power consumption is low. Further, an electronic device which has high heat resistance can be obtained. Further, a long-life electronic device can be obtained.
  • FIGS. 1A to 1C are diagrams each showing a light emitting element of the present invention.
  • FIG. 2 is a diagram showing a light emitting element of the present invention.
  • FIG. 3 is a diagram showing a light emitting element of the present invention.
  • FIGS. 4A and 4B are diagrams showing a light emitting device of the present invention.
  • FIGS. 5A and 5B are diagrams showing a light emitting device of the present invention.
  • FIGS. 6A to 6D are diagrams each showing an electronic device of the present invention.
  • FIG. 7 is a diagram showing an electronic device of the present invention.
  • FIG. 8 is a diagram showing a lighting device of the present invention.
  • FIG. 9 is a diagram showing a lighting device of the present invention.
  • FIG. 10 is a cross-sectional diagram of an organic semiconductor element of the present invention.
  • FIGS. 11A and 11B are 1 H NMR charts of 2,3-bis[4-(4-diphenylaminophenyl)phenyl]quinoxaline (abbrev.: TPAPQ), which is a quinoxaline derivative of the present invention.
  • TPAPQ 2,3-bis[4-(4-diphenylaminophenyl)phenyl]quinoxaline
  • FIG. 12 is a DSC chart of 2,3-bis[4-(4-diphenylaminophenyl)phenyl]quinoxaline (abbrev.: TPAPQ), which is a quinoxaline derivative of the present invention.
  • TPAPQ 2,3-bis[4-(4-diphenylaminophenyl)phenyl]quinoxaline
  • FIG. 13 is a graph showing an absorption spectrum of 2,3-bis[4-(4-diphenylaminophenyl)phenyl]quinoxaline (abbrev.: TPAPQ), which is the quinoxaline derivative of the present invention, in a toluene solution.
  • TPAPQ 2,3-bis[4-(4-diphenylaminophenyl)phenyl]quinoxaline
  • FIG. 14 is a graph showing an absorption spectrum of a thin film of 2,3-bis[4-(4-diphenylaminophenyl)phenyl]quinoxaline (abbrev.: TPAPQ), which is a quinoxaline derivative of the present invention.
  • TPAPQ 2,3-bis[4-(4-diphenylaminophenyl)phenyl]quinoxaline
  • FIG. 15 is a graph showing a light emission spectrum of 2,3-bis[4-(4-diphenylaminophenyl)phenyl]quinoxaline (abbrev.: TPAPQ), which is a quinoxaline derivative of the present invention, in a toluene solution.
  • TPAPQ 2,3-bis[4-(4-diphenylaminophenyl)phenyl]quinoxaline
  • FIGS. 16A and 16B are graphs showing results of CV measurement, in the case of oxidation, of 2,3-bis[4-(4-diphenylaminophenyl)phenyl]quinoxaline (abbrev.: TPAPQ), which is a quinoxaline derivative of the present invention.
  • TPAPQ 2,3-bis[4-(4-diphenylaminophenyl)phenyl]quinoxaline
  • FIGS. 17A and 17B are graphs showing results of CV measurement, in the case of reduction, of 2,3-bis[4-(4-diphenylaminophenyl)phenyl]quinoxaline (abbrev.: TPAPQ), which is a quinoxaline derivative of the present invention.
  • TPAPQ 2,3-bis[4-(4-diphenylaminophenyl)phenyl]quinoxaline
  • FIGS. 18A and 18B are 1 H NMR charts of 2,3-bis[4-(9-phenylcarbazol-3-yl)phenyl]quinoxaline (abbrev.: PCPQ), which is a quinoxaline derivative of the present invention.
  • PCPQ 2,3-bis[4-(9-phenylcarbazol-3-yl)phenyl]quinoxaline
  • FIG. 19 is a DSC chart of 2,3-bis[4-(9-phenylcarbazol-3-yl)phenyl]quinoxaline (abbrev.: PCPQ), which is a quinoxaline derivative of the present invention.
  • PCPQ 2,3-bis[4-(9-phenylcarbazol-3-yl)phenyl]quinoxaline
  • FIG. 20 is a graph showing an absorption spectrum of 2,3-bis[4-(9-phenylcarbazol-3-yl)phenyl]quinoxaline (abbrev.: PCPQ), which is a quinoxaline derivative of the present invention, in a toluene solution.
  • PCPQ 2,3-bis[4-(9-phenylcarbazol-3-yl)phenyl]quinoxaline
  • FIG. 21 is a graph showing an absorption spectrum of a thin film of 2,3-bis[4-(9-phenylcarbazol-3-yl)phenyl]quinoxaline (abbrev.: PCPQ), which is a quinoxaline derivative of the present invention.
  • PCPQ 2,3-bis[4-(9-phenylcarbazol-3-yl)phenyl]quinoxaline
  • FIG. 22 is a graph showing a light emission spectrum of 2,3-bis[4-(9-phenylcarbazol-3-yl)phenyl]quinoxaline (abbrev.: PCPQ), which is a quinoxaline derivative of the present invention, in a toluene solution.
  • PCPQ 2,3-bis[4-(9-phenylcarbazol-3-yl)phenyl]quinoxaline
  • FIG. 23 is a graph showing a light emission spectrum of a thin film of 2,3-bis[4-(9-phenylcarbazol-3-yl)phenyl]quinoxaline (abbrev.: PCPQ), which is a quinoxaline derivative of the present invention.
  • PCPQ 2,3-bis[4-(9-phenylcarbazol-3-yl)phenyl]quinoxaline
  • FIGS. 24A and 24B are graphs showing results of CV measurement, in the case of oxidation, of 2,3-bis[4-(9-phenylcarbazol-3-yl)phenyl]quinoxaline (abbrev.: PCPQ), which is a quinoxaline derivative of the present invention.
  • PCPQ 2,3-bis[4-(9-phenylcarbazol-3-yl)phenyl]quinoxaline
  • FIGS. 25A and 25B are graphs showing results of CV measurement, in the case of reduction, of 2,3-bis[4-(9-phenylcarbazol-3-yl)phenyl]quinoxaline (abbrev.: PCPQ), which is a quinoxaline derivative of the present invention.
  • PCPQ 2,3-bis[4-(9-phenylcarbazol-3-yl)phenyl]quinoxaline
  • FIG. 26 is a diagram showing a light emitting element of an embodiment.
  • FIG. 27 is a graph showing current density versus luminance characteristics of a light emitting element manufactured in Embodiment 3.
  • FIG. 28 is a graph showing voltage versus luminance characteristics of the light emitting element manufactured in Embodiment 3.
  • FIG. 29 is a graph showing luminance versus current efficiency characteristics of the light emitting element manufactured in Embodiment 3.
  • FIG. 30 is a graph showing a light emission spectrum of the light emitting element manufactured in Embodiment 3.
  • FIG. 31 is a graph showing current density versus luminance characteristics of a light emitting element manufactured in Embodiment 4.
  • FIG. 32 is a graph showing voltage versus luminance characteristics of the light emitting element manufactured in Embodiment 4.
  • FIG. 33 is a graph showing luminance versus current efficiency characteristics of the light emitting element manufactured in Embodiment 4.
  • FIG. 34 is a graph showing a light emission spectrum of the light emitting element manufactured in Embodiment 4.
  • FIG. 35 is a graph showing current density versus luminance characteristics of a light emitting element manufactured in Embodiment 5.
  • FIG. 36 is a graph showing voltage versus luminance characteristics of the light emitting element manufactured in Embodiment 5.
  • FIG. 37 is a graph showing luminance versus current efficiency characteristics of the light emitting element manufactured in Embodiment 5.
  • FIG. 38 is a graph showing a light emission spectrum of the light emitting element manufactured in Embodiment 5.
  • FIGS. 39A and 39B are 1 H NMR charts of 2,3-bis ⁇ 4-[4-(carbazole-9-yl)phenyl]phenyl ⁇ quinoxaline (abbrev.: CzPPQ), which is a quinoxaline derivative of the present invention.
  • FIG. 40 is a graph showing an absorption spectrum of 2,3-bis ⁇ 4-[4-(carbazole-9-yl)phenyl]phenyl ⁇ quinoxaline (abbrev.: CzPPQ), which is a quinoxaline derivative of the present invention, in a toluene solution.
  • CzPPQ 2,3-bis ⁇ 4-[4-(carbazole-9-yl)phenyl]phenyl ⁇ quinoxaline
  • FIG. 41 is a graph showing a light emission spectrum of 2,3-bis ⁇ 4-[4-(carbazole-9-yl)phenyl]phenyl ⁇ quinoxaline (abbrev.: CzPPQ), which is a quinoxaline derivative of the present invention, in a toluene solution.
  • CzPPQ 2,3-bis ⁇ 4-[4-(carbazole-9-yl)phenyl]phenyl ⁇ quinoxaline
  • a quinoxaline derivative of the present invention is represented by the general formula (1).
  • R 1 to R 4 may be the same or different and each represent any one of a hydrogen atom, an alkyl group of carbon number 1 to 4, and an aryl group of carbon number 6 to 25.
  • R 1 , R 2 , and R 3 may bond to R 2 , R 3 , and R 4 , respectively, to form a condensed ring.
  • Ar 1 represents an arylene group of carbon number 6 to 25.
  • Ar 2 and Ar 3 may be the same or different and each represent an arylene group of carbon number 6 to 25.
  • Ar 1 and Ar 2 may bond to Ar 2 and Ar 3 , respectively.
  • Ar 1 which is connected to a phenyl group may bond in any one of the ortho position, meta position, and para position on a quinoxaline skeleton.
  • the present invention is preferably a quinoxaline derivative represented by the general formula (2).
  • R 5 to R 18 may be the same or different and each represent any one of a hydrogen atom, an alkyl group of carbon number 1 to 4, and an aryl group of carbon number 6 to 15.
  • R 5 , R 6 , R 7 , R 8 , R 10 , R 11 , R 12 , R 13 , R 15 , and R 17 may bond to R 6 , R 7 , R 8 , R 9 , R 11 , R 12 , R 13 , R 14 , R 16 and R 18 , respectively, to form a condensed ring.
  • the present invention is preferably a quinoxaline derivative represented by the general formula (3).
  • R 19 to R 24 may be the same or different and each represent any one of a hydrogen atom, an alkyl group of carbon number 1 to 4, and an aryl group of carbon number 6 to 15.
  • R 19 , R 20 , R 21 , and R 22 may bond to R 20 , R 21 , R 22 , and R 23 , respectively, to form a condensed ring.
  • the present invention is preferably a quinoxaline derivative represented by the general formula (4).
  • R 25 to R 30 may be the same or different and each represent any one of a hydrogen atom, an alkyl group of carbon number 1 to 4, and an aryl group of carbon number 6 to 15.
  • R 25 and R 27 may bond to R 26 and R 28 , respectively, to form a condensed ring.
  • quinoxaline derivatives represented by the structural formulae (11) to (117) can be given; however, the present invention is not limited thereto.
  • the quinoxaline derivative can be made by a synthetic reaction shown in the synthetic schemes (A-1) to (A-4).
  • a quinoxaline skeleton is formed by a condensation reaction between benzil substituted with halogen atoms X 1 and X 2 (a compound B) and a 1,2-diamino benzene derivative (a compound A).
  • halogen atom bromine, iodine, and chlorine can be given. Considering ease in handling and reactivity, bromine or iodine is preferable.
  • X 1 and X 2 may be the same or different and each represent a hydrogen atom.
  • R 1 to R 4 may be the same or different and each represent any one of a hydrogen atom, an alkyl group of carbon number 1 to 4, and an aryl group of carbon number 6 to 25.
  • R 1 , R 2 , and R 3 may bond to R 2 , R 3 , and R 4 , respectively, to form a condensed ring.
  • organolithium is added to the halogen-substituted quinoxaline thus obtained (a compound C) to perform lithiation of the compound C and is reacted with a boron reagent such as trimethyl borate, triisopropyl borate, or the like, so that boronic acid of a quinoxaline derivative (a compound D) can be obtained.
  • a boron reagent such as trimethyl borate, triisopropyl borate, or the like
  • X 1 and X 2 may be the same or different and each represent a hydrogen atom.
  • the halogen atom bromine, iodine, and chlorine can be given. Considering ease in handling and reactivity, bromine or iodine is preferable.
  • R 1 to R 4 may be the same or different and each represent any one of a hydrogen atom, an alkyl group of carbon number 1 to 4, and an aryl group of carbon number 6 to 25.
  • R 1 , R 2 , and R 3 may bond to R 2 , R 3 , and R 4 , respectively, to form a condensed ring.
  • R 31 to R 33 may be the same or different and each represent any one of a hydrogen atom and an alkyl group of carbon number 1 to 10.
  • the quinoxaline derivative of the present invention can be synthesized by coupling the obtained boronic acid of a quinoxaline derivative (compound D) with a halogenated amine derivative (a compound E) by using a palladium catalyst or monovalent copper in the presence of a base.
  • a base an inorganic base such as potassium carbonate or sodium carbonate, an organic base such as a metal alkoxide, or the like can be used.
  • the palladium catalyst palladium acetate, palladium chloride, bis(dibenzylidineacetone)palladium, or the like can be used.
  • R 1 to R 4 may be the same or different and each represent any one of a hydrogen atom, an alkyl group of carbon number 1 to 4, and an aryl group of carbon number 6 to 25.
  • R 1 , R 2 , and R 3 may bond to R 2 , R 3 , and R 4 , respectively, to form a condensed ring.
  • Ar 1 represents an arylene group of carbon number 6 to 25.
  • Ar 2 and Ar 4 may be the same or different and each represent an arylene group of carbon number 6 to 25.
  • Ar 1 and Ar 2 may bond to Ar 2 and Ar 3 , respectively.
  • X 3 represents a halogen atom.
  • bromine, iodine, and chlorine can be given. Considering ease in handling and reactivity, bromine or iodine is preferable.
  • the quinoxaline derivative of the present invention can be synthesized by coupling the halogen-substituted quinoxaline (compound C) with boronic acid of an amine derivative or an organoboron compound of an amine derivative (a compound F) by using a palladium catalyst or monovalent copper in the presence of a base.
  • a base an inorganic base such as potassium carbonate or sodium carbonate, an organic base such as a metal alkoxide, or the like can be used.
  • the palladium catalyst palladium (II) acetate, tetrakis(triphenylphosphine)palladium (0), or the like can be used.
  • R 1 to R 4 may be the same or different and each represent any one of a hydrogen atom, an alkyl group of carbon number 1 to 4, and an aryl group of carbon number 6 to 25.
  • R 1 , R 2 , and R 3 may bond to R 2 , R 3 , and R 4 , respectively, to form a condensed ring.
  • Ar 1 represents an arylene group of carbon number 6 to 25.
  • Ar 2 and Ar 3 may be the same or different and each represent an arylene group of carbon number 6 to 25.
  • Ar 1 and Ar 2 may bond to Ar 2 and Ar 3 , respectively.
  • R 34 and R 35 may be the same or different and each represent any one of a hydrogen atom and an alkyl group of carbon number 1 to 10.
  • R 34 and R 35 may bond to each other to form a condensed ring.
  • X 1 and X 2 may be the same or different and each represent a halogen atom.
  • the halogen atom bromine, iodine, and chlorine can be given. Considering ease in handling and reactivity, bromine or iodine is preferable.
  • the quinoxaline derivative of the present invention is bipolar and excellent in both electron transporting property and hole transporting property. Therefore, by using the quinoxaline derivative of the present invention for an electronic device, good electric characteristics can be obtained. Further, the quinoxaline derivative of the present invention has a high glass transition point and excellent heat resistance; therefore, by using the quinoxaline derivative of the present invention for an electronic device, an electronic device which has excellent heat resistance can be obtained. Furthermore, the quinoxaline derivative of the present invention is stable with respect to electrochemical oxidation or reduction; therefore, by using the quinoxaline derivative of the present invention for an electronic device, a long-life electronic device can be obtained.
  • a light emitting element of the present invention includes a plurality of layers interposed between a pair of electrodes.
  • the plurality of layers are stacked in which layers each containing a material having a high carrier injecting property or a material having a high carrier transporting property are combined so that a light emitting region is formed apart from the electrodes, that is, so that carriers are recombined at a portion away from the electrodes.
  • the plurality of layers formed between the pair of electrodes is hereinafter referred to as an EL layer.
  • the light emitting element includes a first electrode 102 ; a first layer 103 , a second layer 104 , a third layer 105 , and a fourth layer 106 which are stacked in this order over the first electrode 102 ; and a second electrode 107 provided over the fourth layer 106 .
  • the following description is made assuming that the first electrode 102 functions as an anode and the second electrode 107 functions as a cathode.
  • a substrate 101 is used to support the light emitting element.
  • the substrate 101 for example, glass, plastic, or the like can be used. Any other material may also be used as long as the light emitting element can be supported during a manufacturing process.
  • the first electrode 102 the following is preferably used: a metal, an alloy, a conductive compound, or a mixture thereof, having a high work function (specifically, 4.0 eV or higher).
  • a metal an alloy, a conductive compound, or a mixture thereof, having a high work function (specifically, 4.0 eV or higher).
  • the following can be given: indium tin oxide (ITO); indium tin oxide containing silicon or silicon oxide; indium zinc oxide (IZO); indium oxide containing tungsten oxide and zinc oxide (IWZO); and the like.
  • ITO indium tin oxide
  • IZO indium zinc oxide
  • IWZO indium oxide containing tungsten oxide and zinc oxide
  • a conductive metal oxide film is generally formed by sputtering, it may also be formed by a sol-gel method or the like.
  • indium zinc oxide can be formed by sputtering using a target in which zinc oxide is mixed at 1 wt % to 20 wt % in indium oxide; and indium oxide containing tungsten oxide and zinc oxide (IWZO) can be formed by sputtering using a target in which tungsten oxide at 0.5 wt % to 5 wt % and zinc oxide at 0.1 wt % to 1 wt % are contained in indium oxide.
  • IWZO indium oxide containing tungsten oxide and zinc oxide
  • gold Au
  • platinum Pt
  • nickel Ni
  • tungsten W
  • Cr chromium
  • Mo molybdenum
  • iron Fe
  • Co cobalt
  • Cu copper
  • palladium Pd
  • a nitride of a metal material e.g., titanium nitride
  • the first layer 103 contains a material having a high hole injecting property. Molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, or the like can be used. Further, the first layer 103 can also be formed of a phthalocyanine-based compound such as phthalocyanine (abbrev.: H 2 Pc) or copper phthalocyanine (abbrev.: CuPc); an aromatic amine compound such as 4,4′-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbrev.: DPAB) or 4,4′-bis(N- ⁇ 4-[N-(3-methylphenyl)-N-phenylamino]phenyl ⁇ -N-phenylamino)biphenyl (abbrev.: DNTPD); a high molecule such as poly(ethylene dioxythiophene)/poly(styrenesulfonic acid) (
  • a composite material including an organic compound and an inorganic compound can be used as the first layer 103 .
  • a composite material including an organic compound and an inorganic compound showing an electron-accepting property with respect to the organic compound is excellent in hole injecting property and hole transporting property since electrons are transferred between the organic compound and the inorganic compound and carrier density is increased.
  • the first layer 103 can form an ohmic contact with the first electrode 102 ; therefore, a material of the first electrode can be selected, regardless of work function.
  • an oxide of a transition metal is preferably used.
  • an oxide of a metal in Groups 4 to 8 of the Periodic Table of the Elements can be used as well.
  • the following are preferable because the electron-accepting property is high: vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide.
  • molybdenum oxide is particularly preferable because it is stable in the atmosphere, low in hygroscopicity, and is easy to handle.
  • organic compound used for the composite material various compounds can be used, such as an aromatic amine compound, a carbazole derivative, aromatic amine hydrocarbon, a high molecular weight compound (e.g., an oligomer, a dendrimer, or a polymer).
  • organic compound used for the composite material it is preferable that it is an organic compound having a high hole transporting property. Specifically, it is preferable that it is a material having a hole mobility of 10 ⁇ 6 cm 2 /Vs or more. Further, other materials than these may also be used as long as they are materials in which a hole transporting property is higher than an electron transporting property. Examples of the organic compound which can be used for the composite material are specifically listed below.
  • the aromatic amine compound N,N′-di(p-tolyl)-N,N′-diphenyl-p-phenylenediamine (abbrev.: DTDPPA); 4,4′-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbrev.: DPAB); 4,4′-bis(N- ⁇ 4-[N-(3-methylphenyl)-N-phenylamino]phenyl ⁇ -N-phenylamino)biphenyl (abbrev.: DNTPD); 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbrev.: DPA3B); and the like.
  • DTDPPA 4,4′-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl
  • DPAB 4,4′-bis(
  • carbazole derivative which can be used for the composite material
  • the following can be given: 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbrev.: PCzPCA1); 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbrev.: PCzPCA2); 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbrev.: PCzPCN1); and the like.
  • CBP 4,4′-di(N-carbazolyl)biphenyl
  • TCPB 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene
  • CzPA 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene
  • aromatic hydrocarbon which can be used for the composite material
  • the following can be given: 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbrev.: t-BuDNA); 2-tert-butyl-9,10-di(1-naphthyl)anthracene; 9,10-bis(3,5-diphenylphenyl)anthracene (abbrev.: DPPA); 2-tert-butyl-9,10-bis(4-phenylphenyl)anthracene (abbrev.: t-BuDBA); 9,10-di(2-naphthyl)anthracene (abbrev.: DNA); 9,10-diphenylanthracene (abbrev.: DPAnth); 2-tert-butylanthracene (abbrev.: t-BuAnth); 9,10-bis(4-methyl-1-naphth
  • pentacene, coronene, or the like can also be used.
  • an aromatic hydrocarbon which has a hole mobility of 1 ⁇ 10 ⁇ 6 cm 2 /Vs or more and of which the carbon number is 14 to 42 is more preferable.
  • the aromatic hydrocarbon which can be used for the composite material may have a vinyl skeleton.
  • the aromatic hydrocarbon having a vinyl group 4,4′-bis(2,2-diphenylvinyl)biphenyl (abbrev.: DPVBi), 9,10-bis[4-(2,2-diphenylvinyl)phenyl]anthracene (abbrev.: DPVPA), and the like can be given, for example.
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • a material having a high hole transporting property specifically, an aromatic amine compound (that is; a compound having a benzene ring-nitrogen bond) is preferable.
  • an aromatic amine compound that is; a compound having a benzene ring-nitrogen bond
  • the following can be given: 4,4′-bis[N-(3-methylphenyl)-N-phenylamino]biphenyl; a derivative thereof such as 4,4′-bis[N-(1-napthyl)-N-phenylamino]biphenyl (hereinafter referred to as NPB); and a starburst aromatic amine compound such as 4,4′,4′′-tris(N,N-diphenyl-amino)triphenylamine and 4,4′,4′′-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine.
  • the second layer 104 is not limited to being a single layer and may be a mixed layer of any of the aforementioned materials or a stacked layer which includes two or more layers each containing the aforementioned material.
  • the third layer 105 is a layer containing a light emitting material.
  • the third layer 105 contains the quinoxaline derivative of the present invention described in Embodiment Mode 1.
  • the quinoxaline derivative of the present invention which emits light in blue to blue-green color region, can favorably be applied to a light emitting element as a light emitting material.
  • a material having a high electron transporting property can be used.
  • a layer containing a metal complex or the like including a quinoline or benzoquinoline skeleton such as tris(8-quinolinolato)aluminum (abbrev.: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbrev.: Almq 3 ), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbrev.: BeBq 2 ), or bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum (abbrev.: BAlq) can be used.
  • a metal complex or the like including a quinoline or benzoquinoline skeleton such as tris(8-quinolinolato)aluminum (abbrev.: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbrev.: Almq 3 ),
  • a metal complex or the like including an oxazole-based or thiazole-based ligand such as bis[2-(2-hydroxyphenyl)benzoxazolato]zinc (abbrev.: Zn(BOX) 2 ) or bis[2-(2-hydroxyphenyl)-benzothiazolato]zinc (abbrev.: Zn(BTZ) 2 ) can be used.
  • 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbrev.: PBD); 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbrev.: OXD-7); 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbrev.: TAZ), bathophenanthroline (abbrev.: BPhen); bathocuproine (abbrev.: BCP); or the like.
  • PBD 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole
  • OXD-7 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl
  • the electron transporting layer is not limited to being a single layer and may be a stacked layer which includes two or more layers each containing the aforementioned material.
  • the second electrode 107 the following can be used: a metal, an alloy, a conductive compound, or a mixture thereof, having a low work function (specifically, 3.8 eV or lower).
  • a cathode material the following can be given: an element in Group 1 or 2 of the Periodic Table of the Elements, that is, an alkali metal such as lithium (Li) or cesium (Cs), an alkaline earth metal such as magnesium (Mg), calcium (Ca), or strontium (Sr), and an alloy containing these metals (e.g., MgAg or AlLi).
  • a rare earth metal such as europium (Eu) or ytterbium (Yb), an alloy containing these rare earth metals, and the like can be given.
  • various conductive materials such as Al, Ag, ITO, or ITO containing silicon or silicon oxide can be used as the second electrode 107 , regardless of the value of the work function.
  • an alkali metal, an alkaline earth metal, or a compound thereof such as lithium fluoride (LiF), cesium fluoride (CsF), or calcium fluoride (CaF 2 ) can be used.
  • a layer made of a material having an electron transporting property, which contains an alkali metal, an alkaline earth metal, or a compound thereof e.g., a layer of Alq containing magnesium (Mg)
  • Mg Alq containing magnesium
  • first layer 103 the second layer 104 , the third layer 105 , and the fourth layer 106 .
  • a evaporation method for forming the first layer 103 , the second layer 104 , the third layer 105 , and the fourth layer 106 .
  • an evaporation method for forming the first layer 103 , the second layer 104 , the third layer 105 , and the fourth layer 106 .
  • an evaporation method, an ink-jet method, a spin coating method, or the like can be used.
  • each electrode or each layer may be formed by a different film formation method.
  • the light emitting element of the present invention having the structure as set forth above, current flows due to potential difference between the first electrode 102 and the second electrode 107 and holes and electrons are recombined in the third layer 105 containing the material having a high light emitting property, whereby light emission is performed. That is, a light emitting region is formed in the third layer 105 .
  • either one or both of the first electrode 102 and the second electrode 107 is/are formed using an electrode having a light transmitting property.
  • first electrode 102 has a light transmitting property
  • second electrode 107 is formed using an electrode having a light transmitting property
  • light emission is extracted from the side opposite to the substrate side through the second electrode 107 as shown in FIG. 1B .
  • both of the first electrode 102 and the second electrode 107 are each an electrode having a light transmitting property
  • light emission is extracted from both the substrate side and the side opposite to the substrate side through the first electrode 102 and the second electrode 107 , as shown in FIG. 1C .
  • a layer structure provided between the first electrode 102 and the second electrode 107 is not limited to the above-described one. Any layer structure can be employed as long as a light emitting region, in which holes and electrons are recombined, is provided away from the first electrode 102 and the second electrode 107 , so as to prevent a quenching phenomenon caused by the light emitting region and a metal being located close to each other.
  • a stacked-layer structure of the layers is not particularly limited, and layers formed of a material having a high electron transporting property, a material having a high hole transporting property, a material having a high electron injecting property, a material having a high hole injecting property, a bipolar material (a material having a high electron transporting property and a high hole transporting property), a hole blocking material, or the like may be freely combined with the quinoxaline derivative of the present invention.
  • a light emitting element shown in FIG. 2 has a structure in which a first electrode 302 functioning as a cathode, a first layer 303 formed of a material having a high electron transporting property, a second layer 304 containing a light emitting material, a third layer 305 formed of a material having a high hole transporting property, a fourth layer 306 formed of a material having a high hole injecting property, and a second electrode 307 functioning as an anode are sequentially stacked over a substrate 301 .
  • a light emitting element is manufactured over a substrate made of glass, plastic, or the like.
  • a passive matrix light emitting device can be manufactured.
  • a thin film transistor (TFT) may be formed over a substrate made of glass, plastic, or the like, and a light emitting element electrically connected to the TFT may be manufactured. Accordingly, an active matrix light emitting device in which driving of the light emitting element is controlled by the TFT can be manufactured.
  • the structure of the TFT is not particularly limited, and a staggered TFT or an inverted staggered TFT may be employed.
  • Crystallinity of a semiconductor used for the TFT is also not particularly limited, and an amorphous semiconductor or a crystalline semiconductor may be used.
  • a driving circuit formed over a TFT substrate may include an N-channel TFT and a P-channel TFT or may include either an N-channel TFT or a P-channel TFT.
  • the quinoxaline derivative of the present invention can be used for a light emitting layer without including any other light emitting material since the quinoxaline derivative is bipolar and has a light emitting property.
  • the quinoxaline derivative of the present invention is bipolar, a light emitting element in which a light emitting region is rarely located at an interface of stacked films and which shows favorable characteristics with few changes in the light emission spectrum and little decrease in light emission efficiency due to an interaction such as an exciplex can be manufactured.
  • an amorphous film can be obtained, in which the amount of microcrystalline components included during film formation is very small and that included in the film formed is small. That is, the film quality is good; therefore, a light emitting element with few element defects such as dielectric breakdown due to electric field concentration can be manufactured.
  • the quinoxaline derivative of the present invention which is a material which is bipolar and excellent in carrier transporting property (electron transporting property and hole transporting property), for a light emitting element, a driving voltage of the light emitting element can be reduced and thus the power consumption can be reduced.
  • the quinoxaline derivative of the present invention which has a high glass transition point, a light emitting element having high heat resistance can be obtained.
  • the quinoxaline derivative of the present invention is stable even when an oxidation reaction and a reduction reaction are repeated alternatingly. That is, the quinoxaline derivative is electrochemically stable. Therefore, by using the quinoxaline derivative of the present invention, a long-life light emitting element can be obtained.
  • Embodiment Mode 2 a light emitting element having a different structure from Embodiment Mode 2 is described.
  • various materials can be used as the material in which the quinoxaline derivative of the present invention is dispersed.
  • the materials having a high hole transporting property and the materials having a high electron transporting property which are described in Embodiment Mode 2, the following can be given: 4,4′-di(N-carbazolyl)-biphenyl (abbrev.: CBP); 2,2′,2′′-(1,3,5-benzenetri-yl)-tris[1-phenyl-1H-benzimidazole] (abbrev.: TPBI); 9,10-di(2-naphthyl)anthracene (abbrev.: DNA); 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbrev.: t-BuDNA); and the like.
  • CBP 4,4′-di(N-carbazolyl)-biphenyl
  • TPBI 2,2′,2′′-(1,3,
  • the quinoxaline derivative of the present invention which is a material which is bipolar and excellent in carrier transporting property (electron transporting property and hole transporting property), for a light emitting element, a driving voltage of the light emitting element can be reduced and thus the power consumption can be reduced.
  • the quinoxaline derivative of the present invention which has a high glass transition point, a light emitting element having high heat resistance can be obtained.
  • the quinoxaline derivative of the present invention is stable even when an oxidation reaction and a reduction reaction are repeated alternatingly. That is, the quinoxaline derivative is electrochemically stable. Therefore, by using the quinoxaline derivative of the present invention, a long-life light emitting element can be obtained.
  • Embodiment Mode 2 can be used as appropriate for layers other than the third layer 105 .
  • Embodiment Modes 2 and 3 a light emitting element having a different structure from Embodiment Modes 2 and 3 is described.
  • the quinoxaline derivative of the present invention which is bipolar and has favorable film quality since the amount of microcrystalline components contained during film formation is very small, can be preferably used as the material in which another light emitting material is dispersed.
  • the quinoxaline derivative of the present invention is used as the material in which another light emitting material is dispersed, a light emission color depending on the light emitting material can be obtained. Further, a mixed color of a light emission color depending on the quinoxaline derivative of the present invention and a light emission color depending on the light emitting material dispersed in the quinoxaline derivative can also be obtained.
  • a fluorescent material can be used such as 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran (abbrev.: DCM1), 4-(dicyanomethylene)-2-methyl-6-(julolidine-4-yl-vinyl)-4H-pyran (abbrev.: DCM2), N,N-dimethylquinacridone (abbrev.: DMQd), 9,10-diphenylanthracene (abbrev.: DPA), 5,12-diphenyltetracene (abbrev.: DPT), coumarin 6, perylene, or rubrene.
  • DCM1 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran
  • DCM2 4-(dicyanomethylene)-2-methyl-6-(julolidine-4-yl-vinyl)-4H-pyran
  • DMQd N,N-dimethyl
  • a phosphorescent material can also be used such as bis(2-phenylbenzothiazolato-N,C 2 ′]iridium(III)acetylacetonato (abbrev.: Ir(bt) 2 (acac)), tris(2-phenylquinolinolato-N,C 2 ′]iridium(III) (abbrev.: Ir(pq) 3 ), bis(2-phenylquinolinolato-N,C 2 ′]iridium(III)acetylacetonato (abbrev.: Ir(pq) 2 (acac)), bis[2-(2′-benzo[4,5-a]thienyl)pyridinato-N,C 3 ′]iridium(III)acetylacetonato (abbrev.: Ir(btp) 2 (acac)), bis(1-phenylisoquinolinolato-N,C 2 ′]iridium
  • a light emission spectrum of the phosphorescent material it is preferable that a light emission spectrum of the phosphorescent material have a peak at 560 nm to 700 nm (both inclusive).
  • a light emission spectrum of the fluorescent material it is preferable that a light emission spectrum of the fluorescent material have a peak at 500 nm to 700 nm (both inclusive), and more preferably a peak at 500 nm to 600 nm (both inclusive).
  • the quinoxaline derivative of the present invention which is a material which is bipolar and excellent in carrier transporting property (electron transporting property and hole transporting property), for a light emitting element, a driving voltage of the light emitting element can be reduced.
  • the quinoxaline derivative of the present invention which has a high glass transition point, a light emitting element having high heat resistance can be obtained.
  • the quinoxaline derivative of the present invention is stable even when an oxidation reaction and a reduction reaction are repeated alternatingly. That is, the quinoxaline derivative is electrochemically stable. Therefore, by using the quinoxaline derivative of the present invention, a long-life light emitting element can be obtained.
  • Embodiment Mode 2 can be used as appropriate for layers other than the third layer 105 .
  • This light emitting element is a light emitting element that includes a plurality of light emitting units between a first electrode and a second electrode.
  • a first light emitting unit 511 and a second light emitting unit 512 are stacked between a first electrode 501 and a second electrode 502 . Electrodes similar to those described in Embodiment Mode 2 can be applied to the first electrode 501 and the second electrode 502 .
  • the first light emitting unit 511 and the second light emitting unit 512 may have the same structure or different structures, and a structure similar to any of those described in Embodiment Modes 2 to 4 can be applied.
  • a charge generation layer 513 contains a composite material of an organic compound and a metal oxide.
  • the composite material of an organic compound and a metal oxide is described in Embodiment Mode 2, and contains an organic compound and a metal oxide such as V 2 O 5 , MoO 3 , or WO 3 .
  • the organic compound various compounds such as an aromatic amine compound, a carbazole derivative, an aromatic hydrocarbon, and a high molecular compound (e.g., an oligomer, a dendrimer, or a polymer) can be used. Note that it is preferable that an organic compound having a hole mobility of 10 ⁇ 6 cm 2 /Vs or more be applied as the hole-transporting organic compound.
  • the composite material of an organic compound and a metal oxide is excellent in carrier injecting property and carrier transporting property, and accordingly, low-voltage driving and low-current driving can be realized.
  • the charge generation layer 513 may also be formed of a combination of a composite material of an organic compound and a metal oxide and another material.
  • the charge generation layer 513 may be formed of a combination of a layer containing the composite material of an organic compound and a metal oxide and a layer containing a compound selected from electron donating materials and a compound having a high electron transporting property.
  • the charge generation layer 513 may also be formed of a combination of a layer containing the composite material of an organic compound and a metal oxide and a transparent conductive film.
  • the charge generation layer 513 interposed between the first light emitting unit 511 and the second light emitting unit 512 inject electrons to one light emitting unit and inject holes to the other light emitting unit when a voltage is applied between the first electrode 501 and the second electrode 502 .
  • the light emitting element having two light emitting units is explained; however, the present invention can also be applied to a light emitting element in which three or more light emitting units are stacked together.
  • a long-life light emitting element by which high luminance emission can be realized at a low current density can be realized.
  • the present invention when the present invention is applied to lighting, voltage drop due to resistance of an electrode material can be reduced, and therefore, uniform light emission in a large area can be realized.
  • a light emitting device capable of low-voltage driving and with low power consumption can be realized.
  • This embodiment mode can be combined as appropriate with another embodiment mode.
  • FIG. 4A is a top-view diagram showing the light emitting device
  • FIG. 4B is a cross-sectional diagram of FIG. 4A taken along lines A-A′ and B-B′.
  • a driver circuit portion (a source side driver circuit), a pixel portion, and a driver circuit portion (a gate side driver circuit) are denoted by reference numerals 601 , 602 , and 603 , respectively, and are indicated by using a dotted line.
  • a sealing substrate and a sealing material are denoted by reference numerals 604 and 605 , respectively, and a portion enclosed by the sealing material 605 corresponds to a space 607 .
  • a leading wiring 608 is a wiring for transmitting signals to be input to the source side driver circuit 601 and the gate side driver circuit 603 , and this wiring 608 receives a video signal, a clock signal, a start signal, a reset signal, and the like from an FPC (flexible printed circuit) 609 that is an external input terminal.
  • FPC flexible printed circuit
  • the light emitting device in this specification includes not only a main body of a light emitting device but also a light emitting device provided with an FPC or a PWB.
  • the driver circuit portions and the pixel portion are formed over an element substrate 610 .
  • the source side driver circuit 601 which is one driver circuit portion, and one pixel in the pixel portion 602 are shown.
  • a CMOS circuit which is a combination of an N-channel TFT 623 and a P-channel TFT 624 , is formed as the source side driver circuit 601 .
  • the driver circuit may be formed of any of various CMOS circuits, PMOS circuits, and NMOS circuits. Although a driver-integration type device, in which a driver circuit is formed over a substrate, is described in this embodiment mode, a driver circuit is not necessarily formed over a substrate and can be formed externally as well. Further, the crystallinity of a semiconductor used for the TFT is not particularly limited, and either an amorphous semiconductor or a crystalline semiconductor may be used.
  • the pixel portion 602 includes a plurality of pixels each including a switching TFT 611 , a current controlling TFT 612 , and a first electrode 613 which is electrically connected to a drain of the current controlling TFT 612 .
  • an insulator 614 is formed so as to cover an edge portion of the first electrode 613 .
  • a positive photosensitive acrylic resin film is used for the insulator 614 .
  • the insulator 614 is formed so as to have a curved surface having curvature at an upper end portion or a lower end portion thereof in order to obtain favorable coverage.
  • the insulator 614 is preferably formed so as to have a curved surface with a curvature radius (0.2-3 ⁇ m) only at the upper end portion thereof.
  • a negative type resin which becomes insoluble in an etchant by light irradiation or a positive type resin which becomes soluble in an etchant by light irradiation can be used for the insulator 614 .
  • the first electrode 613 can be formed of, as well as a single-layer film such as an ITO film, an indium tin oxide film containing silicon, an indium oxide film containing zinc oxide at 2 wt % to 20 wt %, a titanium nitride film, a chromium film, a tungsten film, a Zn film, or a Pt film; a stacked layer of a titanium nitride film and a film containing aluminum as its main component; a three-layer film of a titanium nitride film, a film containing aluminum as its main component, and a titanium nitride film; or the like. Note that when a stacked-layer structure is employed for the first electrode 613 , the first electrode 613 is low
  • the EL layer 616 is formed by various methods such as an evaporation method using an evaporation mask, an ink-jet method, and a spin coating method.
  • the EL layer 616 contains the quinoxaline derivative of the present invention described in Embodiment Mode 1 .
  • a low molecular weight compound or a high molecular weight compound e.g., an oligomer or a dendrimer may be used.
  • a material used for the second electrode 617 which is formed over the EL layer 616 and serves as a cathode
  • a material having a small work function e.g., Al, Mg, Li, Ca, or an alloy or a compound thereof such as MgAg, MgIn, AlLi, LiF, or CaF 2
  • a material having a small work function e.g., Al, Mg, Li, Ca, or an alloy or a compound thereof such as MgAg, MgIn, AlLi, LiF, or CaF 2 .
  • a stacked layer of a metal thin film and a transparent conductive film (which is made of ITO, indium oxide containing zinc oxide at 2 wt % to 20 wt %, indium oxide-tin oxide containing silicon or silicon oxide, zinc oxide (ZnO), or the like) is preferably used as the second electrode 617 .
  • a light emitting element 618 is provided in the space 607 enclosed by the element substrate 610 , the sealing substrate 604 , and the sealing material 605 .
  • the space 607 is filled with a filling material; alternatively, it may be filled with an inert gas (e.g., nitrogen or argon) or may be filled with the sealing material 605 .
  • an epoxy-based resin is preferably used as the sealing material 605 . Further, it is preferable that the material transmit as little moisture and oxygen as possible.
  • a plastic substrate made of FRP (Fiberglass-Reinforced Plastics), PVF (polyvinyl fluoride), polyester, an acrylic resin, or the like can be used as well as a glass substrate or a quartz substrate.
  • the quinoxaline derivative of the present invention is electrochemically stabile, a long-life light emitting device can be obtained.
  • the quinoxaline derivative of the present invention is bipolar and is superior in carrier transporting property (electron transporting property and hole transporting property), a driving voltage of a light emitting element and power consumption of a light emitting device can be reduced by use of the quinoxaline derivative of the present invention.
  • a phosphorescent material is used as a light emitting material, a light emitting device with high light emission efficiency and further reduced power consumption can be obtained.
  • FIGS. 5A and 5B are perspective diagrams of a passive matrix light emitting device which is manufactured by applying the present invention.
  • an EL layer 955 is provided between electrodes 952 and 956 over a substrate 951 .
  • An edge of the electrode 952 is covered with an insulating layer 953 .
  • a partition layer 954 is provided over the insulating layer 953 .
  • a side wall of the partition layer 954 slopes so that a distance between one side wall and the other side wall is narrower toward a substrate surface.
  • a cross section of the partition layer 954 in the direction of a short side is trapezoidal, and a base (a side extending in a similar direction as a plane direction of the insulating layer 953 and in contact with the insulating layer 953 ) is shorter than an upper side (a side extending in a similar direction as the plane direction of the insulating layer 953 and not in contact with the insulating layer 953 ).
  • an electronic device of the present invention including the light emitting device described in Embodiment Mode 6 is described.
  • the electronic device of the present invention contains the quinoxaline derivative described in Embodiment Mode 1 and has a display portion that has high heat resistance. Further, a long-life display portion is provided. Further, a display portion with reduced power consumption is provided.
  • an electronic device including a light emitting element manufactured using the quinoxaline derivative of the present invention
  • a camera such as a video camera or a digital camera, a goggle type display, a navigation system, an audio reproducing device (e.g., a car audio system or an audio component system), a computer, a game machine, a portable information terminal (e.g., a mobile computer, a mobile phone, a portable game machine, or an electronic book), an image reproducing device provided with a recording medium (specifically, a device capable of reproducing a recording medium such as a Digital Versatile Disc (DVD) and provided with a display device that can display the image), and the like are given. Specific examples of these electronic devices are shown in FIGS. 6A to 6D .
  • FIG. 6A shows a television device according to the present invention, which includes a housing 9101 , a supporting base 9102 , a display portion 9103 , a speaker portion 9104 , a video input terminal 9105 , and the like.
  • the display portion 9103 includes light emitting elements similar to any of those described in Embodiment Modes 2 to 5, arranged in matrix.
  • the light emitting element has features in that low voltage driving can be performed and the life is long. Further, there is also a feature in that the heat resistance is high.
  • the display portion 9103 including the light emitting elements has similar features. Therefore, in the television device, image degradation is suppressed and low power consumption is achieved.
  • a deterioration compensation function and a power supply circuit can be significantly reduced or downsized in the television device, which enables reduction in size and weight of the housing 9101 and the supporting base 9102 .
  • the television device according to the present invention low power consumption, high image quality, and small size and lightweight are achieved; therefore, a product which is suitable for living environment can be provided.
  • FIG. 6B shows a computer according to the present invention, which includes a main body 9201 , a housing 9202 , a display portion 9203 , a keyboard 9204 , an external connection port 9205 , a pointing device 9206 , and the like.
  • the display portion 9203 includes light emitting elements similar to any of those described in Embodiment Modes 2 to 5, arranged in matrix.
  • the light emitting element has features in that low voltage driving can be performed and the life is long. Further, there is also a feature in that the heat resistance is high.
  • the display portion 9203 including the light emitting elements has similar features. Therefore, in the computer, image degradation is suppressed and low power consumption is achieved.
  • a deterioration compensation function and a power supply circuit can be significantly reduced or downsized in the computer, which enables reduction in size and weight of the main body 9201 and the housing 9202 .
  • the computer according to the present invention low power consumption, high image quality, and small size and lightweight are achieved; therefore, a product which is suitable for environment can be provided.
  • FIG. 6C shows a mobile phone according to the present invention, which includes a main body 9401 , a housing 9402 , a display portion 9403 , an audio input portion 9404 , an audio output portion 9405 , an operation key 9406 , an external connection port 9407 , an antenna 9408 , and the like.
  • the display portion 9403 includes light emitting elements similar to any of those described in Embodiment Modes 2 to 5, arranged in matrix.
  • the light emitting element has features in that low voltage driving can be performed and the life is long. Further, there is also a feature in that the heat resistance is high.
  • the display portion 9403 including the light emitting elements has similar features.
  • a deterioration compensation function and a power supply circuit can be significantly reduced or downsized in the mobile phone, which enables reduction in size and weight of the main body 9401 and the housing 9402 .
  • low power consumption, high image quality, and small size and lightweight are achieved; therefore, a product which is suitable for mobile use can be provided.
  • FIG. 6D shows a camera according to the present invention, which includes a main body 9501 , a display portion 9502 , a housing 9503 , an external connection port 9504 , a remote control receiving portion 9505 , an image receiving portion 9506 , a battery 9507 , an audio input portion 9508 , operation keys 9509 , an eye piece portion 9510 , and the like.
  • the display portion 9502 includes light emitting elements similar to any of those described in Embodiment Modes 2 to 5 , arranged in matrix.
  • the light emitting element has features in that low voltage driving can be performed and the life is long. Further, there is also a feature in that the heat resistance is high.
  • the display portion 9502 including the light emitting elements has similar features.
  • a deterioration compensation function and a power supply circuit can be significantly reduced or downsized in the camera, which enables reduction in size and weight of the main body 9501 .
  • low power consumption, high image quality, and small size and lightweight are achieved; therefore, a product which is suitable for mobile use can be provided.
  • the applicable range of the light emitting device of the present invention is so wide that the light emitting device can be applied to electronic devices in various fields.
  • an electronic device which has a display portion with low power consumption, a long life, and high heat resistance can be provided.
  • the light-emitting device of the present invention can also be used as a lighting device.
  • One mode where the light emitting element of the present invention is used as a lighting device is described with reference to FIG. 7 .
  • FIG. 7 shows an example of a liquid crystal display device using the light emitting device of the present invention as a backlight.
  • the liquid crystal display device shown in FIG. 7 includes a housing 901 , a liquid crystal layer 902 , a backlight 903 , and a housing 904 , and the liquid crystal layer 902 is connected to a driver IC 905 .
  • the light emitting device of the present invention is used for the backlight 903 , and current is supplied through a terminal 906 .
  • the backlight with reduced power consumption can be obtained.
  • the light emitting device of the present invention is a lighting device with plane light emission and can have a large area
  • the backlight can have a large area, and a liquid crystal display device having a large area can be obtained.
  • the light emitting device of the present invention is thin and the power consumption is low, reduction in thickness and power consumption of a display device can also be achieved.
  • the light emitting device of the present invention has a long life and high heat resistance
  • a liquid crystal display device using the light emitting device of the present invention also has a long life and high heat resistance.
  • FIG. 8 shows an example where the light emitting device to which the present invention is applied is used as a table lamp that is a lighting device.
  • a table lamp shown in FIG. 8 includes a housing 2001 and a light source 2002 , and the light emitting device of the present invention is used as the light source 2002 . Since the light emitting device of the present invention has high light emission efficiency and a long life, the table lamp also has high light emission efficiency and a long life.
  • FIG. 9 shows an example where a light emitting device to which the present invention is applied is used as an indoor lighting device 3001 .
  • the light emitting device of the present invention which can also have a large area can be used as a lighting device having a large area. Further, the light emitting device of the present invention which is thin and of which power consumption is low can be used as a lighting device which is thin and of which power consumption is low.
  • a television device 3002 according to the present invention like that shown in FIG. 6A , is placed in a room where the light emitting device to which the present invention is applied is used as the indoor lighting device 3001 , and public broadcasting and movies can be enjoyed. In such a case, since power consumption of both devices is small, dynamic images can be enjoyed in a bright room without any concern about an electricity bill.
  • the element has a structure in which a thin-film active layer 1202 containing the quinoxaline derivative of the present invention is interposed between a source electrode 1201 and a drain electrode 1203 , and a gate electrode 1204 is embedded in the active layer 1202 , as shown in FIG. 10 .
  • the gate electrode 1204 is electrically connected to a means for applying a gate voltage
  • the source electrode 1201 and the drain electrode 1203 are electrically connected to a means for controlling the source-drain voltage.
  • the element when a voltage is applied between source and drain under the condition where a gate voltage is not applied, a current flows (the state is an ON state). When a gate voltage is applied in this state, a depletion layer is generated in the periphery of the gate electrode 1204 , whereby a current does not flow (the state is an OFF state). With the aforementioned mechanism, the element operates as a transistor.
  • a material which has both a carrier transporting property and an excellent film quality is required for an active layer.
  • the quinoxaline derivative of the present invention is useful since it sufficiently meets this requirement.
  • TPAPQ 2,3-bis[4-(4-diphenylaminophenyl)phenyl]quinoxaline
  • the obtained solid was dissolved in toluene, and the resulting solution was subjected to suction filtration with florisil, celite, and alumina.
  • the filtrate was enriched, whereby 30.0 g of a white powder solid of 2,3-bis(4-bromophenyl)quinoxaline that was a subject matter was obtained at a yield of 99%.
  • a synthesis method of 4-bromotriphenylamine is described.
  • a synthesis scheme of 4-bromotriphenylamine is shown in (B-3).
  • TPAPQ 2,3-bis[4-(4-diphenylaminophenyl)phenyl]quinoxaline
  • FIGS. 11A and 11B An 1 H NMR chart is shown in FIGS. 11A and 11B .
  • FIG 11 B is an enlarged chart of FIG. 11A in the range of 6.0 ppm to 9.0 ppm.
  • TG-DTA Thermogravimetry-Differential Thermal Analysis
  • a Thermo-Gravimetric/Differential Thermal Analyzer (TG/-DTA-320, manufactured by SII NanoTechnology Inc.) was used, and thermophysical properties were evaluated under a nitrogen atmosphere with a rising temperature of 10° C./min. Consequently, from the gravity-temperature relationship (thermogravimetric measurement), the temperature at which the gravity was 95% or less of the gravity at the starting point of the measurement was, under normal pressure, 460° C. Thus, high heat resistance was exhibited.
  • a glass transition point of TPAPQ was measured with a differential scanning calorimeter (DSC; Pyris 1, manufactured by Perkin Elmer Co., Ltd.). First, a sample thereof was heated to 300° C. at 40° C./min to dissolve the test sample and then cooled to room temperature at 40° C./min. After that, the temperature was increased to 300° C. at 10° C./min. In this manner, a DSC chart shown in FIG. 12 was obtained. From this chart, it was found that a glass transition point (Tg) and a melting point of TPAPQ were 121° C. and 235° C. respectively. Accordingly, it was found that TPAPQ has a high glass transition point.
  • DSC differential scanning calorimeter
  • an absorption spectrum of toluene solution of TPAPQ is shown in FIG. 13 .
  • an absorption spectrum of thin film of TPAPQ is shown in FIG. 14 .
  • An ultraviolet-visible spectrophotometer (type V550, manufactured by Japan Spectroscopy Corporation) was used for the measurement.
  • the solution was contained in a quartz cell, and the thin film was deposited over a quartz substrate.
  • Each absorption spectrum of the solution and the thin film shown in FIGS. 13 and 14 was obtained by subtracting the spectrum of the quartz.
  • a horizontal axis indicates wavelength (nm) and a vertical axis indicates absorption intensity (unit is arbitrary).
  • FIG. 15 An emission spectrum of the toluene solution of TPAPQ (excitation wavelength: 375 nm) is shown in FIG. 15 .
  • a horizontal axis indicates wavelength (nm) and a vertical axis indicates emission intensity (unit is arbitrary).
  • the maximum emission wavelength was 475 nm (excitation wavelength: 375 nm).
  • an ionization potential of TPAPQ in the state of thin film which was measured with a photoelectron spectroscopy device (AC-2, manufactured by Riken Keiki Co., Ltd.) in the atmosphere, was 5.44 eV. Accordingly, it was found that the HOMO level thereof was ⁇ 5.44 eV. Further, using data from FIG. 14 on the absorption spectrum of thin film of TPAPQ, an absorption edge was found from a Tauc plot for direct transition assumed, and the absorption edge was estimated as an optical energy gap; the energy gap was 2.83 eV. The LUMO level which was found from the resulting energy gap value and the HOMO level was ⁇ 2.61 eV.
  • TPAPQ electrochemical stability of TPAPQ was evaluated by cyclic voltammetry (CV).
  • An electrochemical analyzer (ALS model 600A, manufactured by BAS, Inc.) was used as the measuring device.
  • the solution for the CV measurement was prepared by using dehydrated dimethylformamide (DMF) as a solvent, dissolving tetra-n-butylammonium perchlorate (n-Bu 4 NClO 4 ), which is a supporting electrolyte, to a concentration of 100 mM and dissolving TPAPQ, which is an object of the measurement, to a concentration of 1 mM.
  • DMF dehydrated dimethylformamide
  • n-Bu 4 NClO 4 tetra-n-butylammonium perchlorate
  • a platinum electrode (PTE platinum electrode, manufactured by BAS, Inc.) was used as a working electrode
  • another platinum electrode (Pt counter electrode (5 cm) for VC-3, manufactured by BAS, Inc.) was used as an auxiliary electrode
  • an Ag/Ag + electrode (RE5 non-aqueous solvent reference electrode, manufactured by BAS, Inc.) was used as a reference electrode.
  • the scanning speed was set at 0.1 V/sec, and a 100-cycle CV measurement was conducted for each of an oxidation case and a reduction case.
  • FIGS. 16A and 16B show the results of CV measurement in the oxidation case of TPAPQ
  • FIGS. 17A and 17B show the results of CV measurement in the reduction case of TPAPQ
  • FIG. 16A shows the measurement result at the beginning of the measurement
  • FIG. 16B shows the measurement result after 100 cycles
  • FIG. 17A shows the measurement result at the beginning of the measurement
  • FIG. 17B shows the measurement result after 100 cycles. It was found that a reversible peak is obtained in either of the oxidation case and the reduction case. In addition, even if oxidation or reduction is repeated 100 times, each peak position hardly changes. This means that TPAPQ is stable with respect to oxidation and reduction, that is, it is electrochemically stable.
  • PCPQ 2,3-bis[4-(9-phenylcarbazol-3-yl)phenyl]quinoxaline
  • PCPQ 2,3-bis[4-(9-phenylcarbazol-3-yl)phenyl]quinoxaline
  • FIGS. 18A and 18B An 1 H NMR chart is shown in FIGS. 18A and 18B .
  • FIG. 18B is an enlarged chart of FIG. 18A in the range of 7.0 ppm to 9.0 ppm.
  • TG-DTA Thermogravimetry-Differential Thermal Analysis
  • a Thermo-Gravimetric/Differential Thermal Analyzer (TG/-DTA-320, manufactured by SII NanoTechnology Inc.) was used, and thermophysical properties were evaluated under a nitrogen atmosphere with a rising temperature of 10° C./min. Consequently, from the gravity-temperature relationship (thermogravimetric measurement), the temperature at which the gravity was 95% or less of the gravity at the starting point of the measurement was, under normal pressure, 425° C. Thus, high heat resistance was exhibited.
  • a glass transition point of PCPQ was measured with a differential scanning calorimeter (DSC; Pyris 1, manufactured by Perkin Elmer Co., Ltd.). First, a sample thereof was heated to 380° C. at 40° C./min and then cooled to room temperature at 40° C./min. After that, the temperature was increased to 380° C. at 10° C./min. In this manner, a DSC chart shown in FIG. 19 was obtained. From this chart, it was found that the glass transition point (Tg) was 154° C. Accordingly, it was found that PCPQ has a high glass transition point. Note that because of a high amorphous nature of PCPQ, a peak indicating a melting point was not observed.
  • DSC differential scanning calorimeter
  • FIG. 20 an absorption spectrum of toluene solution of PCPQ is shown in FIG. 20 .
  • an absorption spectrum of thin film of PCPQ is shown in FIG. 21 .
  • An ultraviolet-visible spectrophotometer (type V550, manufactured by Japan Spectroscopy Corporation) was used for the measurement.
  • the solution was contained in a quartz cell, and the thin film was deposited over a quartz substrate.
  • Each absorption spectrum of the solution and the thin film shown in FIGS. 20 and 21 was obtained by subtracting the spectrum of the quartz.
  • a horizontal axis indicates wavelength (nm) and a vertical axis indicates absorption intensity (unit is arbitrary).
  • FIG. 22 An emission spectrum of the toluene solution of PCPQ (excitation wavelength: 298 nm) is shown in FIG. 22 .
  • FIG. 23 an emission spectrum of the thin film of PCPQ (excitation wavelength: 400 nm) is shown in FIG. 23 .
  • a horizontal axis indicates wavelength (nm) and a vertical axis indicates emission intensity (unit is arbitrary).
  • the maximum emission wavelength was 441 nm (excitation wavelength: 298 nm) for the toluene solution, and was 495 nm (excitation wavelength: 400 nm) for the thin film.
  • an ionization potential of PCPQ in the state of thin film which was measured with a photoelectron spectroscopy device (AC-2, manufactured by Riken Keiki Co.,Ltd.) in the atmosphere, was 5.57 eV. Accordingly, it was found that the HOMO level thereof was ⁇ 5.57 eV. Further, using data on the absorption spectrum of thin film of PCPQ, an absorption edge was found from a Tauc plot for direct transition assumed, and the absorption edge was estimated as an optical energy gap; the energy gap was 2.94 eV. The LUMO level which was found from the resulting energy gap value and the HOMO level was ⁇ 2.63 eV.
  • the electrochemical stability of PCPQ was evaluated by cyclic voltammetry (CV).
  • An electrochemical analyzer (ALS model 600A, manufactured by BAS, Inc.) was used as the measuring device.
  • the solution for the CV measurement was prepared by using dehydrated dimethylformamide (DMF) as a solvent, dissolving tetra-n-butylammonium perchlorate (n-Bu 4 NClO 4 ), which is a supporting electrolyte, to a concentration of 100 mM and dissolving PCPQ, which is an object of the measurement, to a concentration of 1 mM.
  • DMF dehydrated dimethylformamide
  • n-Bu 4 NClO 4 tetra-n-butylammonium perchlorate
  • PCPQ which is an object of the measurement
  • a platinum electrode (PTE platinum electrode, manufactured by BAS, Inc.) was used as a working electrode
  • another platinum electrode (Pt counter electrode (5 cm) for VC-3, manufactured by BAS, Inc.) was used as an auxiliary electrode
  • an Ag/Ag + electrode (RE5 non-aqueous solvent reference electrode, manufactured by BAS, Inc.) was used as a reference electrode.
  • the scanning speed was set at 0.1 V/sec, and a 100-cycle CV measurement was conducted for each of an oxidation case and a reduction case.
  • FIGS. 24A and 24B show the results of CV measurement in the oxidation case of PCPQ
  • FIGS. 25A and 25B show the results of CV measurement in the reduction case of PCPQ
  • FIG. 24A shows the measurement result at the beginning of the measurement
  • FIG. 24B shows the measurement result after 100 cycles
  • FIG. 25A shows the measurement result at the beginning of the measurement
  • FIG. 25B shows the measurement result after 100 cycles.
  • the light emitting element of the present invention is described with reference to FIG. 26 .
  • the chemical formula of a material used in this embodiment is shown below.
  • indium tin oxide containing silicon oxide (ITSO) was formed over a glass substrate 2101 by sputtering to form a first electrode 2102 .
  • a thickness thereof was set to 110 nm and an electrode area was set to 2 mm ⁇ 2 mm.
  • the co-evaporation method means an evaporation method by which evaporation is concurrently conducted from a plurality of evaporation sources in one treatment chamber.
  • NPB 4,4′-bis[N-(1-napthyl)-N-phenylamino]biphenyl
  • a light emitting layer 2105 having a thickness of 30 nm was formed over the hole transporting layer 2104 by co-evaporation of 2,3-bis[4-(4-diphenylaminophenyl)phenyl]quinoxaline (abbrev.: TPAPQ), which is the quinoxaline derivative of the present invention represented by the structural formula (11), and (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]jiridium(III) (abbrev.: Ir(Fdpq) 2 (acac)).
  • TPAPQ 2,3-bis[4-(4-diphenylaminophenyl)phenyl]quinoxaline
  • Ir(Fdpq) 2 (acac) acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]jiridium(III)
  • tris(8-quinolinolato)aluminum (abbrev.: Alq) was deposited to have a film thickness of 10 nm over the light emitting layer 2105 by an evaporation method using resistance heating, whereby an electron transporting layer 2106 was formed.
  • an electron injecting layer 2107 having a thickness of 50 nm was formed over the electron transporting layer 2106 by co-evaporation of tris(8-quinolinolato)aluminum (abbrev.: Alq) and lithium.
  • Alq tris(8-quinolinolato)aluminum
  • Comparative Light Emitting Element 1 was manufactured similarly to Light Emitting Element 1 except for a light emitting layer, and the light emitting layer was formed by co-evaporation of NPB and Ir(Fdpq) 2 (acac).
  • FIG. 27 shows current density versus luminance characteristics of Light Emitting Element 1 and Comparative Light Emitting Element 1. Further, FIG. 28 shows voltage versus luminance characteristics of the same. Further, FIG. 29 shows luminance versus current efficiency characteristics of the same. Further, FIG. 30 shows a light emission spectrum when a current of 1 mA is supplied.
  • the current efficiency was 2.0 cd/A
  • the voltage was 6.8 V
  • the current density was 46.6 mA/cm 2
  • the power efficiency was 0.931 m/W.
  • the maximum emission wavelength when the current of 1 mA was supplied was 648 nm.
  • the current efficiency was 2.8 cd/A
  • the voltage was 6.4 V
  • the current density was 33.1 mA/cm 2
  • the power efficiency was 1.41 m/W.
  • the maximum emission wavelength when the current of 1 mA was supplied was 649 nm.
  • the quinoxaline derivative of the present invention which is bipolar, a light emitting element in which a driving voltage is reduced can be obtained. Further, by using the quinoxaline derivative of the present invention, a light emitting element in which the light emission efficiency is high can be obtained. Further, by using the quinoxaline derivative of the present invention, a light emitting element in which the power efficiency is high, that is, the power consumption is low, can be obtained.
  • the light emitting element of the present invention is described with reference to FIG. 26 .
  • a method for manufacturing a light emitting element of this embodiment is described below.
  • indium tin oxide containing silicon oxide (ITSO) containing silicon oxide was formed over the glass substrate 2101 by sputtering to form the first electrode 2102 .
  • a thickness thereof was set to 110 nm and an electrode area was set to 2 mm ⁇ 2 mm.
  • the co-evaporation method means an evaporation method by which evaporation is concurrently conducted from a plurality of evaporation sources in one treatment chamber.
  • NPB 4,4′-bis[N-(1-napthyl)-N-phenylamino]biphenyl
  • the light emitting layer 2105 having a thickness of 30 nm was formed over the hole transporting layer 2104 by co-evaporation of 2,3-bis[4-(9-phenylcarbazol-3-yl)phenyl]quinoxaline (abbrev.: PCPQ), which is the quinoxaline derivative of the present invention represented by the structural formula (12), and (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbrev.: Ir(Fdpq) 2 (acac)).
  • tris(8-quinolinolato)aluminum (abbrev.: Alq) was deposited to have a film thickness of 10 nm over the light emitting layer 2105 by an evaporation method using resistance heating, whereby the electron transporting layer 2106 was formed.
  • the electron injecting layer 2107 having a thickness of 50 nm was formed over the electron transporting layer 2106 by co-evaporation of tris(8-quinolinolato)aluminum (abbrev.: Alq) and lithium.
  • Alq tris(8-quinolinolato)aluminum
  • FIG. 31 shows current density versus luminance characteristics of Light Emitting Element 2. Further, FIG. 32 shows voltage versus luminance characteristics of the same. Further, FIG. 33 shows luminance versus current efficiency characteristics of the same. Further, FIG. 34 shows a light emission spectrum when a current of 1 mA is supplied.
  • the current efficiency was 3.1 cd/A
  • the voltage was 7.4 V
  • the current density was 37.2 mA/cm 2
  • the power efficiency was 1.31 m/W.
  • the external quantum efficiency was 6.9%.
  • the maximum emission wavelength when the current of 1 mA was supplied was 652 nm.
  • the quinoxaline derivative of the present invention which is bipolar, a light emitting element in which a driving voltage is reduced can be obtained. Further, by using the quinoxaline derivative of the present invention, a light emitting element in which the light emission efficiency is high can be obtained. Further, by using the quinoxaline derivative of the present invention, a light emitting element in which the external quantum efficiency is high can be obtained. Further, by using the quinoxaline derivative of the present invention, a light emitting element in which the power efficiency is high, that is, the power consumption is low, can be obtained.
  • the light emitting element of the present invention is described with reference to FIG. 26 .
  • a method for manufacturing a light emitting element of this embodiment is described below.
  • indium tin oxide containing silicon oxide (ITSO) containing silicon oxide was formed over the glass substrate 2101 by sputtering to form the first electrode 2102 .
  • a thickness thereof was set to 110 nm and an electrode area was set to 2 mm ⁇ 2 mm.
  • the co-evaporation method means an evaporation method by which evaporation is concurrently conducted from a plurality of evaporation sources in one treatment chamber.
  • NPB 4,4′-bis[N-(1-napthyl)-N-phenylamino]biphenyl
  • the light emitting layer 2105 having a thickness of 30 nm was formed over the hole transporting layer 2104 by co-evaporation of 2,3-bis[4-(9-phenylcarbazol-3-yl)phenyl]quinoxaline (abbrev.: PCPQ), which is the quinoxaline derivative of the present invention represented by the structural formula (12), and (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbrev.: Ir(Fdpq) 2 (acac)).
  • 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (bathocuproin, abbrev.: BCP) was deposited to have a film thickness of 10 nm over the light emitting layer 2105 by an evaporation method using resistance heating, whereby the electron transporting layer 2106 was formed.
  • the electron injecting layer 2107 having a thickness of 50 nm was formed over the electron transporting layer 2106 by co-evaporation of tris(8-quinolinolato)aluminum (abbrev.: Alq) and lithium.
  • Alq tris(8-quinolinolato)aluminum
  • FIG. 35 shows current density versus luminance characteristics of Light Emitting Element 3. Further, FIG. 36 shows voltage versus luminance characteristics of the same. Further, FIG. 37 shows luminance versus current efficiency characteristics of the same. Further, FIG. 38 shows a light emission spectrum when a current of 1 mA is supplied.
  • the current efficiency was 3.4 cd/A
  • the voltage was 8.4 V
  • the current density was 27.2 mA/cm 2
  • the power efficiency was 1.31 m/W.
  • the external quantum efficiency was 8.5%.
  • the maximum emission wavelength when the current of 1 mA was supplied was 650 nm.
  • a light emitting element in which the light emission efficiency is further increased can be obtained. Further, a light emitting element in which external quantum efficiency is high can be obtained. Further, a light emitting element in which the power efficiency is high, that is, the power consumption is low, can be obtained.
  • FIGS. 39A and 39B An 1 H NMR chart is shown in FIGS. 39A and 39B .
  • FIG. 39B is an enlarged chart of FIG. 39A in the range of 7.0 ppm to 10.0 ppm.
  • TG-DTA Thermogravimetry-Differential Thermal Analysis
  • a Thermo-Gravimetric/Differential Thermal Analyzer (TG/-DTA-320, manufactured by SII NanoTechnology Inc.) was used, and thermophysical properties were evaluated under a nitrogen atmosphere with a rising temperature of 10° C./min. Consequently, from the gravity-temperature relationship (thermogravimetric measurement), the temperature at which the gravity was 95% or less of the gravity at the starting point of the measurement was, under normal pressure, 500° C. or higher. Thus, high heat resistance was exhibited.
  • FIG. 40 An absorption spectrum of toluene solution of CzPPQ is shown in FIG. 40 .
  • An ultraviolet-visible spectrophotometer (type V550, manufactured by Japan Spectroscopy Corporation) was used for the measurement.
  • the solution was contained in a quartz cell, and the thin film was deposited over a quartz substrate.
  • the absorption spectrum of the solution shown in FIG. 40 was obtained by subtracting the spectrum of the quartz.
  • a horizontal axis indicates wavelength (nm) and a vertical axis indicates absorption intensity (unit is arbitrary).
  • absorption was observed at around 280 nm, 290 nm, and 340 nm.
  • an emission spectrum of the toluene solution of CzPPQ (excitation wavelength: 340 nm) is shown in FIG. 41 .
  • a horizontal axis indicates wavelength (nm) and a vertical axis indicates emission intensity (unit is arbitrary).
  • the maximum emission wavelength was 420 nm (excitation wavelength: 340 nm) for the toluene solution.

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US20080122350A1 (en) * 2006-11-29 2008-05-29 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light emitting device, electronic appliance, and method of manufacturing the same
US20090072718A1 (en) * 2007-02-28 2009-03-19 Semiconductor Energy Laboratory Co., Ltd. Quinoxaline derivative, and light-emitting element, light-emitting device, and electronic device including quinoxaline derivative
US7931974B2 (en) 2006-09-29 2011-04-26 Semiconductor Energy Laboratory Co., Ltd. Quinoxaline derivative, and light-emitting device, electronic device using the quinoxaline derivative
US20120242936A1 (en) * 2006-09-29 2012-09-27 Semiconductor Energy Laboratory Co., Ltd. Quinoxaline Derivative, and Light Emitting Element, Light Emitting Device, and Electronic Device Using the Quinoxaline Derivative
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US9741969B2 (en) 2015-08-24 2017-08-22 National Tsing Hua University Carrier generation material and organic light-emitting diode
US9899608B2 (en) 2010-03-01 2018-02-20 Semiconductor Energy Laboratory Co., Ltd. Heterocyclic compound, light-emitting element, light-emitting device, electronic device, and lighting device
US10424755B2 (en) 2012-04-06 2019-09-24 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, electronic device, and lighting device each comprising light-emitting layer with mixed organic compounds capable of forming exciplex
CN114621151A (zh) * 2022-03-25 2022-06-14 南京邮电大学 热活化延迟荧光半导体材料及其制备方法与应用
US11674082B2 (en) 2018-05-03 2023-06-13 Lg Chem, Ltd. Polymerizable liquid crystal compound, liquid crystal composition for optical element, polymer, optically anisotropic body, and optical element for display device

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US7696348B2 (en) 2006-03-21 2010-04-13 Semiconductor Energy Laboratories Co., Ltd. Quinoxaline derivative, and light-emitting element, light-emitting device, electronic device using the quinoxaline derivative
US20100141130A1 (en) * 2006-03-21 2010-06-10 Semiconductor Energy Laboratory Co., Ltd. Quinoxaline derivative, and light-emitting element, light-emitting device, electronic device using the quinoxaline derivative
US8471017B2 (en) 2006-03-21 2013-06-25 Semiconductor Energy Laboratory Co. Ltd. Quinoxaline derivative, and light-emitting element, light-emitting device, electronic device using the quinoxaline derivative
US8008489B2 (en) 2006-03-21 2011-08-30 Semiconductor Energy Laboratory Co., Ltd. Quinoxaline derivative, and light-emitting element, light-emitting device, electronic device using the quinoxaline derivative
US20070222374A1 (en) * 2006-03-21 2007-09-27 Masakazu Egawa Quinoxaline derivative, and light-emitting element, light-emitting device, electronic device using the quinoxaline derivative
US8252433B2 (en) 2006-09-29 2012-08-28 Semiconductor Energy Laboratory Co., Ltd. Quinoxaline derivative, and light-emitting device, electronic device using the quinoxaline derivative
US9062036B2 (en) 2006-09-29 2015-06-23 Semiconductor Energy Laboratory Co., Ltd. Quinoxaline derivative, and light emitting element, light emitting device, and electronic device using the quinoxaline derivative
US8703305B2 (en) * 2006-09-29 2014-04-22 Semiconductor Energy Laboratory Co., Ltd. Quinoxaline derivative, and light emitting element, light emitting device, and electronic device using the quinoxaline derivative
US9328098B2 (en) 2006-09-29 2016-05-03 Semiconductor Energy Laboratory Co., Ltd. Quinoxaline derivative, and light emitting element, light emitting device, and electronic device using the quinoxaline derivative
US7931974B2 (en) 2006-09-29 2011-04-26 Semiconductor Energy Laboratory Co., Ltd. Quinoxaline derivative, and light-emitting device, electronic device using the quinoxaline derivative
US20110198574A1 (en) * 2006-09-29 2011-08-18 Semiconductor Energy Laboratory Co., Ltd. Quinoxaline Derivative, and Light-Emitting Device, Electronic Device Using the Quinoxaline Derivative
US20120242936A1 (en) * 2006-09-29 2012-09-27 Semiconductor Energy Laboratory Co., Ltd. Quinoxaline Derivative, and Light Emitting Element, Light Emitting Device, and Electronic Device Using the Quinoxaline Derivative
US7911135B2 (en) * 2006-11-29 2011-03-22 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light emitting device, electronic appliance, and method of manufacturing the same
US8231424B2 (en) 2006-11-29 2012-07-31 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, electronic appliance, and method of manufacturing the same
US20110143474A1 (en) * 2006-11-29 2011-06-16 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, electronic appliance, and method of manufacturing the same
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US20080122350A1 (en) * 2006-11-29 2008-05-29 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light emitting device, electronic appliance, and method of manufacturing the same
US8178216B2 (en) * 2007-02-28 2012-05-15 Semiconductor Energy Laboratory Co., Ltd. Quinoxaline derivative, and light-emitting element, light-emitting device, and electronic device including quinoxaline derivative
US20090072718A1 (en) * 2007-02-28 2009-03-19 Semiconductor Energy Laboratory Co., Ltd. Quinoxaline derivative, and light-emitting element, light-emitting device, and electronic device including quinoxaline derivative
CN102725268A (zh) * 2010-01-25 2012-10-10 默克专利有限公司 用于电子器件的化合物
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US9899608B2 (en) 2010-03-01 2018-02-20 Semiconductor Energy Laboratory Co., Ltd. Heterocyclic compound, light-emitting element, light-emitting device, electronic device, and lighting device
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US10424755B2 (en) 2012-04-06 2019-09-24 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, electronic device, and lighting device each comprising light-emitting layer with mixed organic compounds capable of forming exciplex
US9741969B2 (en) 2015-08-24 2017-08-22 National Tsing Hua University Carrier generation material and organic light-emitting diode
US11674082B2 (en) 2018-05-03 2023-06-13 Lg Chem, Ltd. Polymerizable liquid crystal compound, liquid crystal composition for optical element, polymer, optically anisotropic body, and optical element for display device
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