WO2013145923A1 - Élément électroluminescent organique - Google Patents

Élément électroluminescent organique Download PDF

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WO2013145923A1
WO2013145923A1 PCT/JP2013/053767 JP2013053767W WO2013145923A1 WO 2013145923 A1 WO2013145923 A1 WO 2013145923A1 JP 2013053767 W JP2013053767 W JP 2013053767W WO 2013145923 A1 WO2013145923 A1 WO 2013145923A1
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group
substituted
carbon atoms
unsubstituted
ring
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Japanese (ja)
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由美子 水木
光則 伊藤
井上　哲也
茎子 日比野
西村　和樹
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出光興産株式会社
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Priority claimed from PCT/JP2012/081382 external-priority patent/WO2013084885A1/fr
Priority claimed from US13/760,928 external-priority patent/US9530969B2/en
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Publication of WO2013145923A1 publication Critical patent/WO2013145923A1/fr

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    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H05B33/00—Electroluminescent light sources
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Definitions

  • the present invention relates to an organic electroluminescence element.
  • an organic electroluminescence element (hereinafter also referred to as an organic EL element)
  • holes from the anode and electrons from the cathode are injected into the light emitting layer.
  • the injected holes and electrons are recombined to form excitons.
  • singlet excitons and triplet excitons are generated at a ratio of 25%: 75% according to the statistical rule of electron spin.
  • the fluorescence type uses light emitted from singlet excitons, and therefore the internal quantum efficiency of the organic EL element is said to be limited to 25%.
  • the phosphorescent type since light emission by triplet excitons is used, it is known that the internal quantum efficiency can be increased to 100% when intersystem crossing is efficiently performed from singlet excitons.
  • an optimal element design has been made according to a light emission mechanism of a fluorescent type and a phosphorescent type.
  • phosphorescent organic EL elements cannot obtain high-performance elements by simple diversion of fluorescent element technology because of their light emission characteristics.
  • the reason is generally considered as follows.
  • phosphorescence emission is emission using triplet excitons
  • the energy gap of the compound used for the light emitting layer must be large. This is because the value of the singlet energy of a compound (the energy difference between the lowest excited singlet state and the ground state) is usually the triplet energy of the compound (the energy between the lowest excited triplet state and the ground state). This is because it is larger than the value of the difference.
  • a host material having a triplet energy larger than the triplet energy of the phosphorescent dopant material must be used for the light emitting layer. I must.
  • a compound having a triplet energy larger than that of the phosphorescent dopant material must be used for the electron transport layer and the hole transport layer.
  • hydrocarbon compounds having high oxidation resistance and reduction resistance useful for fluorescent elements have a large energy gap due to the large spread of ⁇ electron clouds. Therefore, in the phosphorescent organic EL element, such a hydrocarbon compound is difficult to select, and an organic compound containing a hetero atom such as oxygen or nitrogen is selected. As a result, the phosphorescent organic EL element is There is a problem that the lifetime is shorter than that of a fluorescent organic EL element.
  • the exciton relaxation rate of the triplet exciton of the phosphorescent dopant material is much longer than that of the singlet exciton also greatly affects the device performance. That is, since light emitted from singlet excitons has a high relaxation rate that leads to light emission, the diffusion of excitons to the peripheral layers of the light-emitting layer (for example, a hole transport layer or an electron transport layer) hardly occurs and is efficient. Light emission is expected. On the other hand, light emission from triplet excitons is spin-forbidden and has a slow relaxation rate, so that excitons are likely to diffuse to the peripheral layer, and thermal energy deactivation occurs from other than specific phosphorescent compounds. End up.
  • control of the recombination region of electrons and holes is more important than the fluorescent organic EL element.
  • material selection and element design different from those of fluorescent organic EL elements are required.
  • Patent Documents 1 and 2 describe that a compound in which a nitrogen-containing heterocyclic group is introduced into a biscarbazole skeleton in which two carbazoles are linked is used as a host material in a light emitting layer of a phosphorescent organic EL element. .
  • the compounds described in Patent Documents 1 and 2 have a molecular design that balances charge transport by introducing an electron-deficient nitrogen-containing heterocyclic group into a hole-transporting carbazole skeleton.
  • Patent Document 3 discloses that a longer lifetime can be obtained by mixing a plurality of host materials in the light emitting layer. Examination of combinations of various host materials to be mixed Has been made. However, the organic EL element is desired to have a longer lifetime.
  • An object of the present invention is to provide a long-life organic electroluminescence element.
  • An organic electroluminescence device comprising at least a light emitting layer between an anode and a cathode, wherein the light emitting layer is represented by a first host material represented by the following general formula (A) and the following general formula (1):
  • An organic electroluminescence device comprising: a second host material; and a light emitting material.
  • a 1 and A 2 each independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • a 3 represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
  • m represents an integer of 0 to 3.
  • X 1 to X 8 and Y 1 to Y 8 each independently represent N or CR a .
  • R a is independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, substituted or unsubstituted It represents a substituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted silyl group, a halogen atom or a cyano group. When a plurality of R a are present, the plurality of R a may be the same or different. One of X 5 to X 8 and one of Y 1 to Y 4 are bonded via A 3 .
  • At least one of A 1 and A 2 is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with a cyano group, or a hetero ring having 5 to 30 ring atoms substituted with a cyano group. It is a cyclic group.
  • At least one of X 1 to X 4 and Y 5 to Y 8 is CR a , and at least one of R a in X 1 to X 4 and Y 5 to Y 8 is substituted with a cyano group It is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a heterocyclic group having 5 to 30 ring atoms substituted with a cyano group.
  • m is an integer of 1 to 3, and at least one of A 3 is substituted with a divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with a cyano group, or a cyano group And a divalent heterocyclic group having 5 to 30 ring atoms.
  • At least one of X 5 to X 8 and Y 1 to Y 4 is CR a , and at least one of R a in X 5 to X 8 and Y 1 to Y 8 is substituted with a cyano group It is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a heterocyclic group having 5 to 30 ring atoms substituted with a cyano group.
  • At least one of X 1 to X 8 and Y 1 to Y 8 is C—CN.
  • Z 1 represents a ring structure represented by the following general formula (1-1) or (1-2) condensed in a.
  • Z 2 represents a ring structure represented by the following general formula (1-1) or (1-2) condensed at b. However, at least one of Z 1 and Z 2 is represented by the following general formula (1-1).
  • M 1 is a substituted or unsubstituted nitrogen-containing heteroaromatic ring having 5 to 30 ring atoms
  • L 1 represents a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, a ring It represents a cycloalkylene group having 5 to 30 carbon atoms formed or a group in which these are linked.
  • k represents 1 or 2.
  • c represents condensation in a or b in the general formula (1).
  • any one of d, e and f represents condensation in a or b in the general formula (1).
  • X 11 represents a sulfur atom, an oxygen atom, N—R 19 , or C (R 20 ) (R 21 ).
  • R 11 to R 21 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted ring formation.
  • Adjacent R 11 to R 21 may be bonded to each other to form a ring.
  • a 3 represents a substituted or unsubstituted divalent monocyclic hydrocarbon group having 6 or less ring carbon atoms, or a substituted or unsubstituted divalent monocyclic hydrocarbon group having 6 or less ring atoms.
  • Z 1 represents a ring structure represented by the general formula (1-1) or (1-2) condensed in a.
  • Z 2 represents a ring structure represented by the general formula (1-1) or (1-2) condensed at b.
  • at least one of Z 1 and Z 2 is represented by the general formula (1-1).
  • L 1 has the same meaning as L 1 in Formula (1).
  • X 12 to X 14 are each independently a nitrogen atom, CH, or a carbon atom bonded to R 31 or L 1, and at least one of X 12 to X 14 is a nitrogen atom.
  • Y 11 to Y 13 each independently represent CH or a carbon atom bonded to R 31 or L 1 .
  • R 31 each independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 3 30 to 30 alkylsilyl groups, substituted or unsubstituted arylsilyl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 30 carbon atoms Or a substituted or unsubstituted
  • R 31 there are a plurality a plurality of R 31 may be the same or different from each other and, R 31 may be bonded to each other to form a ring adjacent.
  • k represents 1 or 2
  • n represents an integer of 0 to 4.
  • C in the general formula (1-1) is condensed in a or b in the general formula (2); Any one of d, e and f in the general formula (1-2) is condensed in a or b in the general formula (2).
  • [Formula (3) Medium L 1 has the same meaning as L 1 in Formula (1).
  • X 12 to X 14 are each independently a nitrogen atom, CH, or a carbon atom bonded to R 31 or L 1, and at least one of X 12 to X 14 is a nitrogen atom.
  • Y 11 to Y 13 each independently represent CH or a carbon atom bonded to R 31 or L 1 .
  • R 31 each independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 3 30 to 30 alkylsilyl groups, substituted or unsubstituted arylsilyl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 30 carbon atoms Or a substituted or unsubstituted
  • R 31 there are a plurality a plurality of R 31 may be the same or different from each other and, R 31 may be bonded to each other to form a ring adjacent.
  • n represents an integer of 0 to 4.
  • R 41 to R 48 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted ring formation.
  • Adjacent R 41 to R 48 may be bonded to each other to form a ring. ] 6). 6. The organic electroluminescence device according to any one of 1 to 5, wherein the first host material satisfies only the item (i). 7). 7. The organic electroluminescence device according to any one of 1 to 6, wherein the second host material is represented by the following general formula (4).
  • L 1 has the same meaning as L 1 in Formula (1).
  • X 12 to X 14 are each independently a nitrogen atom, CH, or a carbon atom bonded to R 31 or L 1, and at least one of X 12 to X 14 is a nitrogen atom.
  • Y 11 to Y 13 each independently represent CH or a carbon atom bonded to R 31 or L 1 .
  • R 31 each independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 3 30 to 30 alkylsilyl groups, substituted or unsubstituted arylsilyl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 30 carbon atoms Or a substituted or unsubstituted
  • R 31 there are a plurality a plurality of R 31 may be the same or different from each other and, R 31 may be bonded to each other to form a ring adjacent.
  • n represents an integer of 0 to 4.
  • L 2 and L 3 each independently represent a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted 2 to 5 ring atom having 2 to 30 ring atoms.
  • a valent heterocyclic group, a cycloalkylene group having 5 to 30 ring carbon atoms, or a group in which these are connected is represented.
  • R 51 to R 54 each independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • R 51 there are a plurality a plurality of R 51 may be the same or different, and, R 51 may be bonded to each other to form a ring adjacent.
  • R 52 there are a plurality a plurality of R 52 may be the same or different, and, R 52 may be bonded to each other to form a ring adjacent.
  • R 53 there are a plurality a plurality of R 53 may be the same or different, and, R 53 may be bonded to each other to form a ring adjacent.
  • R 54 there are a plurality the plurality of R 54 may be the same or different from each other and, R 54 may be bonded to each other to form a ring adjacent.
  • M 2 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • p and s each independently represent an integer of 0 to 4, and q and r each independently represents an integer of 0 to 3. ] 8).
  • at least one of A 1 and A 2 is substituted with a phenyl group substituted with a cyano group, a naphthyl group substituted with a cyano group, a phenanthryl group substituted with a cyano group, or a cyano group.
  • the organic electroluminescence device according to any one of 1 to 7 above. 9. 9.
  • the organic electro luminescence according to any one of 1 to 8 above, wherein the luminescent material contains a phosphorescent luminescent material which is an orthometalated complex of a metal atom selected from iridium (Ir), osmium (Os) and platinum (Pt). Luminescence element. 10. 10. The organic electroluminescence device as described in 9 above, wherein the phosphorescent material has an emission peak wavelength of 490 nm to 700 nm.
  • a long-life organic electroluminescence device can be provided.
  • FIG. 1 is a schematic cross-sectional view showing an example of the organic EL element of the present invention.
  • organic electroluminescence device of the present invention includes at least a light emitting layer between an anode and a cathode, and the light emitting layer is represented by the following general formula (A). It contains a first host material represented, a second host material represented by the following general formula (1), and a light emitting material.
  • a 1 and A 2 each independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • a 3 represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
  • m represents an integer of 0 to 3.
  • X 1 to X 8 and Y 1 to Y 8 each independently represent N or CR a .
  • R a is independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, substituted or unsubstituted It represents a substituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted silyl group, a halogen atom or a cyano group. When a plurality of R a are present, the plurality of R a may be the same or different. One of X 5 to X 8 and one of Y 1 to Y 4 are bonded via A 3 .
  • At least one of A 1 and A 2 is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with a cyano group, or a hetero ring having 5 to 30 ring atoms substituted with a cyano group. It is a cyclic group.
  • At least one of X 1 to X 4 and Y 5 to Y 8 is CR a , and at least one of R a in X 1 to X 4 and Y 5 to Y 8 is substituted with a cyano group It is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a heterocyclic group having 5 to 30 ring atoms substituted with a cyano group.
  • m is an integer of 1 to 3, and at least one of A 3 is substituted with a divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with a cyano group, or a cyano group And a divalent heterocyclic group having 5 to 30 ring atoms.
  • At least one of X 5 to X 8 and Y 1 to Y 4 is CR a , and at least one of R a in X 5 to X 8 and Y 1 to Y 8 is substituted with a cyano group It is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a heterocyclic group having 5 to 30 ring atoms substituted with a cyano group.
  • At least one of X 1 to X 8 and Y 1 to Y 8 is C—CN.
  • an aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with a cyano group, or a heterocyclic group having 5 to 30 ring atoms substituted with a cyano group is further represented by cyano You may have substituents other than group.
  • the m is preferably 0 to 2, more preferably 0 or 1. When m is 0, one of X 5 to X 8 and one of Y 1 to Y 4 are bonded through a single bond.
  • Examples of the aromatic hydrocarbon group having 6 to 30 ring carbon atoms represented by A 1 , A 2 and R a include a non-condensed aromatic hydrocarbon group and a condensed aromatic hydrocarbon group, and more specifically, , Phenyl group, naphthyl group, phenanthryl group, biphenyl group, terphenyl group, quarterphenyl group, fluoranthenyl group, triphenylenyl group, phenanthrenyl group, fluorenyl group, spirofluorenyl group, 9,9-diphenylfluorenyl group 9,9′-spirobi [9H-fluoren] -2-yl group, 9,9-dimethylfluorenyl group, benzo [c] phenanthrenyl group, benzo [a] triphenylenyl group, naphtho [1,2-c] Phenanthrenyl group, naphtho [1,2-a] triphenylenyl group, dibenzo [
  • Examples of the heterocyclic group having 5 to 30 ring atoms represented by A 1 , A 2 and R a include a non-condensed heterocyclic group and a condensed heterocyclic group, and more specifically, a pyrrole ring, an isoindole Ring, benzofuran ring, isobenzofuran ring, dibenzothiophene ring, isoquinoline ring, quinoxaline ring, phenanthridine ring, phenanthroline ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring , Pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan ring, thiophene ring, oxazole ring, ox
  • Examples of the divalent heterocyclic group having 5 to 30 ring atoms represented by A 3 include a divalent group described above for the heterocyclic group having 5 to 30 ring atoms.
  • Examples of the alkyl group having 1 to 30 carbon atoms represented by Ra include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, cyclopropyl group, cyclobuty
  • Examples of the substituted or unsubstituted silyl group represented by Ra include trimethylsilyl group, triethylsilyl group, tributylsilyl group, dimethylethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, Dimethylisopropylsilyl group, dimethylpropylsilyl group, dimethylbutylsilyl group, dimethyltertiarybutylsilyl group, diethylisopropylsilyl group, phenyldimethylsilyl group, diphenylmethylsilyl group, diphenyltertiarybutylsilyl group, triphenylsilyl group, etc.
  • a trimethylsilyl group a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, and a propyldimethylsilyl group are preferable.
  • halogen atom represented by Ra examples include fluorine, chlorine, bromine, iodine and the like, and fluorine is preferred.
  • R a is preferably a hydrogen atom or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
  • a halogen atom fluorine, chlorine, bromine, iodine
  • a cyano group a carbon number of 1
  • An alkyl group having 20 to 20 preferably 1 to 6
  • a cycloalkyl group having 3 to 20 carbon atoms preferably 5 to 12
  • an alkoxy group having 1 to 20 carbon atoms preferably 1 to 5
  • 1 to 20 preferably 1 to 5)
  • haloalkyl group 1 to 20 carbon atom (preferably 1 to 5) haloalkoxy group, 1 to 10 carbon atom (preferably 1 to 5) alkylsilyl group, ring-forming carbon number
  • Aromatic hydrocarbon group having 6 to 30 preferably 6 to 18
  • aryloxy group having 6 to 30 ring carbon atoms preferably 6 to 18
  • aryl having 6 to 30 carbon atoms preferably 6 to 18 carbon atoms
  • alkyl group having 1 to 20 carbon atoms used as the optional substituent include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t -Butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n -Tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group and the like.
  • cycloalkyl group having 3 to 20 carbon atoms used as the optional substituent include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclooctyl group, adamantyl group and the like.
  • alkoxy group having 1 to 20 carbon atoms used as the optional substituent include groups in which the alkyl moiety is the alkyl group.
  • haloalkyl group having 1 to 20 carbon atoms used as the optional substituent include groups in which part or all of the hydrogen atoms of the alkyl group are substituted with halogen atoms.
  • haloalkoxy group having 1 to 20 carbon atoms used as the optional substituent include groups in which part or all of the above-described alkoxy groups are substituted with halogen atoms.
  • alkylsilyl group having 1 to 10 carbon atoms used as the optional substituent include trimethylsilyl group, triethylsilyl group, tributylsilyl group, dimethylethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group.
  • Propyldimethylsilyl group dimethylisopropylsilyl group, dimethylpropylsilyl group, dimethylbutylsilyl group, dimethyltertiarybutylsilyl group, diethylisopropylsilyl group and the like.
  • aromatic hydrocarbon group having ring carbon atoms of 6 to 30 for use as the optional substituents may be the same as those aromatic hydrocarbon group indicated by the A 1, A 2 and R a.
  • aryloxy group having 6 to 30 ring carbon atoms used as the optional substituent include groups in which the aryl moiety is the aromatic hydrocarbon group.
  • arylsilyl group having 6 to 30 carbon atoms used as the optional substituent include a phenyldimethylsilyl group, a diphenylmethylsilyl group, a diphenyl tertiary butylsilyl group, and a triphenylsilyl group.
  • aralkyl group having 7 to 30 carbon atoms used as the optional substituent include benzyl group, 2-phenylpropan-2-yl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenyl.
  • the optional substituent is preferably a fluorine atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a heteroaryl group having 5 to 30 ring atoms.
  • the above arbitrary substituents may further have a substituent, and specific examples thereof are the same as the above arbitrary substituents.
  • carbon number ab in the expression “substituted or unsubstituted X group having carbon number ab” represents the number of carbons when X group is unsubstituted. The carbon number of the substituent when the X group is substituted is not included.
  • the hydrogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (protium), deuterium (triuterium), and tritium.
  • the groups represented by the above formulas (a) and (b) are X 6- (A 3 ) m -Y 3 , X 6- (A 3 ).
  • m -Y 2, X 7 - ( a 3) is preferably attached at either the binding position of m -Y 3. That is, a compound represented by any one of the following formulas (II), (III), and (IV) is more preferable.
  • X 1 to X 8 , Y 1 to Y 8 , A 1 to A 3 and m are X 1 to X 8 and Y 1 to Y in the formula (A), respectively. 8 , the same as A 1 to A 3 and m.
  • the formulas (II), (III), and (IV) are the same as the conditions (i) to (v) in the formula (A). Meet)
  • the first host material represented by the above formula (A) satisfies at least one of the above (i) to (v). That is, a cyano group is introduced into a biscarbazole derivative to which groups represented by the above formulas (a) and (b) are linked.
  • the first host material has improved hole resistance by introducing an electron injection / transport cyano group. Therefore, the organic EL device of the present invention containing the first host material having a cyano group has an effect of extending the life as compared with the conventional organic EL device using a host material having no cyano group.
  • a 3 in the general formula (A) is a single bond, a substituted or unsubstituted divalent monocyclic hydrocarbon group having 6 or less ring carbon atoms, or a substituted or unsubstituted divalent hydrocarbon group having 6 or less ring atoms. It is preferable to represent the monocyclic heterocyclic group. Examples of the monocyclic hydrocarbon group having 6 or less ring carbon atoms represented by A 3 include a phenylene group, a cyclopentenylene group, a cyclopentadienylene group, a cyclohexylene group, a cyclopentylene group, and the like. A phenylene group is preferred.
  • Examples of the monocyclic heterocyclic group having 6 or less ring atoms represented by A 3 include a pyrrolylene group, a pyrazinylene group, a pyridinylene group, a furylene group, and a thiophenylene group.
  • a 3 is preferably a substituted or unsubstituted monocyclic hydrocarbon group having 6 or less ring-forming carbon atoms, or a substituted or unsubstituted monocyclic heterocyclic group having 6 or less ring-forming atoms.
  • HOMO the highest occupied molecular orbital
  • m is 0 and one of X 5 to X 8 and one of Y 1 to Y 4 are bonded via a single bond, or A 3 is a substituted or unsubstituted phenylene group. Is preferred.
  • the first host material preferably satisfies at least one of the following (i) and the following (ii).
  • the first host material preferably corresponds to one of the following (1) to (3). (1) The above (i) is satisfied, and the above (ii) to (v) are not satisfied. (2) The above (ii) is satisfied, and the above (i) and (iii) to (v) are not satisfied. (3) Both the above (i) and (ii) are satisfied, and the above (iii) to (v) are not satisfied.
  • the first host material satisfying the above (i) and / or (ii) has a cyano group on the terminal side of the central skeleton with respect to the central skeleton having the group represented by the above formulas (a) and (b). It is a structure in which a heterocyclic group having an aromatic hydrocarbon group or a cyano group is introduced.
  • the central skeleton having a group represented by the above formulas (a) and (b) functions as a hole injection / transport unit, and an aromatic hydrocarbon group having a cyano group or a heterocyclic group having a cyano group is Functions as an electron injection / transport unit.
  • a group having a cyano group functioning as an electron injecting / transporting unit is introduced outside the central skeleton. While maintaining the spread of the electron cloud of the occupied molecular orbital) and maintaining good hole injection / transport properties, it also has the function of electron injection / transport properties by the group having a cyano group.
  • fills said (i) or (ii) becomes favorable in the carrier balance in a molecule
  • the organic EL device of the present invention including a light emitting layer containing a first host material satisfying at least one of the above (i) and (ii) and a second host material represented by the formula (1).
  • the luminous efficiency of the organic EL element is improved.
  • At least one of A 1 and A 2 is substituted with a phenyl group substituted with a cyano group, a naphthyl group substituted with a cyano group, or a cyano group
  • a phenanthryl group dibenzofuranyl group substituted with cyano group, dibenzothiophenyl group substituted with cyano group, biphenyl group substituted with cyano group, terphenyl group substituted with cyano group, substituted with cyano group 9,9-diphenylfluorenyl group, 9,9′-spirobi [9H-fluoren] -2-yl group substituted with a cyano group, 9,9′-dimethylfluorenyl substituted with a cyano group Or a triphenylenyl group substituted with a cyano group, preferably a 3′-cyanobiphenyl-2-yl group, a
  • a -2-yl group and a 7-cyanotriphenylene-2-yl group are more preferable.
  • a 1 is preferably substituted with a cyano group
  • a 2 is preferably
  • the first host material if the condition is satisfied in the (ii), at least one of X 1 ⁇ X 4 and Y 5 ⁇ Y 8 is CR a, X 1 ⁇ X 4 and Y 5 ⁇ Y 8 At least one of R a is a phenyl group substituted with a cyano group, a naphthyl group substituted with a cyano group, a phenanthryl group substituted with a cyano group, a dibenzofuranyl group substituted with a cyano group, or a cyano group Substituted dibenzothiophenyl group, biphenyl group substituted with cyano group, terphenyl group substituted with cyano group, 9,9-diphenylfluorenyl group substituted with cyano group, 9 substituted with cyano group , 9′-spirobi [9H-fluoren] -2-yl group, 9,9′-dimethylfluorenyl group
  • the A 1 and the A 2 are preferably different from each other. Among them, it is more preferable that the group A 1 is substituted with a cyano group and the group A 2 is not substituted with a cyano group. That is, the first host material preferably has an asymmetric structure, and the first host material has good crystallinity and non-crystallinity due to such a structure. Therefore, since the organic EL element using the first host material has excellent film quality, for example, high performance can be achieved in organic EL characteristics such as current efficiency.
  • the method for producing the first host material is not particularly limited and may be produced by a known method. For example, it is described in Tetrahedron 40 (1984) 1435-1456 for carbazole derivatives and aromatic halogenated compounds. It can be produced by a coupling reaction using a copper catalyst or a palladium catalyst described in Journal of American Chemical Society 123 (2001) 7727-7729.
  • the second host material contained in the light emitting layer of the organic EL device of the present embodiment is a compound represented by the following general formula (1).
  • Z 1 represents a ring structure represented by the following general formula (1-1) or (1-2) condensed in a.
  • Z 2 represents a ring structure represented by the following general formula (1-1) or (1-2) condensed at b.
  • at least one of Z 1 and Z 2 is represented by the following general formula (1-1).
  • M 1 is a substituted or unsubstituted nitrogen-containing heteroaromatic ring having 5 to 30 ring atoms
  • L 1 represents a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, a ring It represents a cycloalkylene group having 5 to 30 carbon atoms formed or a group in which these are linked.
  • k represents 1 or 2.
  • c represents condensation in a or b in the general formula (1).
  • Any one of d, e and f represents condensation in a or b in the general formula (1).
  • X 11 represents a sulfur atom, an oxygen atom, N—R 19 , or C (R 20 ) (R 21 ).
  • R 11 to R 21 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted ring formation.
  • Adjacent R 11 to R 21 may be bonded to each other to form a ring.
  • the “nitrogen-containing heteroaromatic ring” represented by M 1 in the general formula (1) includes an azine ring.
  • Examples of the nitrogen-containing heteroaromatic ring represented by M 1 in the general formula (1) include pyridine, pyrimidine, pyrazine, triazine, aziridine, azaindolizine, indolizine, imidazole, indole, isoindole, indazole, purine, Examples include pteridine, ⁇ -carboline, naphthyridine, quinoxaline, terpyridine, bipyridine, acridine, phenanthroline, phenazine, and imidazopyridine.
  • pyridine, pyrimidine, and triazine are preferable, and represented by the following general formula (2) Those are also preferred.
  • Z 1 represents a ring structure represented by the general formula (1-1) or (1-2) condensed in a.
  • Z 2 represents a ring structure represented by the general formula (1-1) or (1-2) condensed at b.
  • at least one of Z 1 and Z 2 is represented by the general formula (1-1).
  • L 1 has the same meaning as L 1 in Formula (1).
  • X 12 to X 14 are each independently a nitrogen atom, CH, or a carbon atom bonded to R 31 or L 1, and at least one of X 12 to X 14 is a nitrogen atom.
  • Y 11 to Y 13 each independently represent CH or a carbon atom bonded to R 31 or L 1 .
  • R 31 each independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 3 30 to 30 alkylsilyl groups, substituted or unsubstituted arylsilyl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 30 carbon atoms Or a substituted or unsubstituted
  • R 31 there are a plurality a plurality of R 31 may be the same or different from each other and, R 31 may be bonded to each other to form a ring adjacent.
  • k represents 1 or 2
  • n represents an integer of 0 to 4.
  • C in the general formula (1-1) is condensed in a or b in the general formula (2); Any one of d, e and f in the general formula (1-2) is condensed in a or b in the general formula (2).
  • examples of the compound in which the general formulas (1-1) and (2-2) are condensed in a and b in the general formula (2) include those represented by the following general formula.
  • the compound represented by the general formulas (1) and (2) is more preferably represented by the following general formula (3), and particularly preferably represented by the following general formula (4).
  • L 1 has the same meaning as L 1 in Formula (1).
  • X 12 to X 14 are each independently a nitrogen atom, CH, or a carbon atom bonded to R 31 or L 1, and at least one of X 12 to X 14 is a nitrogen atom.
  • Y 11 to Y 13 each independently represent CH or a carbon atom bonded to R 31 or L 1 .
  • R 31 each independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 3 30 to 30 alkylsilyl groups, substituted or unsubstituted arylsilyl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 30 carbon atoms Or a substituted or unsubstituted
  • R 31 there are a plurality a plurality of R 31 may be the same or different from each other and, R 31 may be bonded to each other to form a ring adjacent.
  • n represents an integer of 0 to 4.
  • R 41 to R 48 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted ring formation.
  • Adjacent R 41 to R 48 may be bonded to each other to form a ring.
  • L 1 has the same meaning as L 1 in Formula (1).
  • X 12 to X 14 are each independently a nitrogen atom, CH, or a carbon atom bonded to R 31 or L 1, and at least one of X 12 to X 14 is a nitrogen atom.
  • Y 11 to Y 13 each independently represent CH or a carbon atom bonded to R 31 or L 1 .
  • R 31 each independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 3 30 to 30 alkylsilyl groups, substituted or unsubstituted arylsilyl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 30 carbon atoms Or a substituted or unsubstituted
  • R 31 may be bonded to each other to form a ring.
  • n represents an integer of 0 to 4.
  • L 2 and L 3 each independently represent a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted 2 to 5 ring atom having 2 to 30 ring atoms.
  • a valent heterocyclic group, a cycloalkylene group having 5 to 30 ring carbon atoms, or a group in which these are connected is represented.
  • R 51 to R 54 each independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • R 51 there are a plurality a plurality of R 51 may be the same or different, and, R 51 may be bonded to each other to form a ring adjacent.
  • R 52 there are a plurality a plurality of R 52 may be the same or different, and, R 52 may be bonded to each other to form a ring adjacent.
  • R 53 there are a plurality a plurality of R 53 may be the same or different, and, R 53 may be bonded to each other to form a ring adjacent.
  • R 54 there are a plurality the plurality of R 54 may be the same or different from each other and, R 54 may be bonded to each other to form a ring adjacent.
  • M 2 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • p and s each independently represent an integer of 0 to 4
  • q and r each independently represents an integer of 0 to 3.
  • each group represented by R 11 to R 21 , R 31 , R 41 to R 48 and R 51 to R 54 Is a group described in the compound represented by the general formula (A).
  • Examples of the group include a group corresponding to the divalent group described for the compound represented by the general formula (A).
  • Examples of the compound represented by any one of the above general formulas (1) to (4) include the following.
  • a bond having no chemical formula (CN, benzene ring, or the like) at its end represents a methyl group.
  • the organic EL device of the present invention may have a hole transport layer, a light emitting layer, a space layer, a barrier layer, and the like, and these include the same compounds as the first host material and the second host material described above. You may go out.
  • Examples of the light emitting material contained in the light emitting layer include a fluorescent light emitting material and a phosphorescent light emitting material, and a phosphorescent light emitting material is preferable.
  • the organic EL element of the present invention may be a fluorescent or phosphorescent monochromatic light emitting element, a fluorescent / phosphorescent hybrid white light emitting element, or a simple type having a single light emitting unit.
  • a tandem type having a plurality of light emitting units may be used, and among them, a phosphorescent type is preferable.
  • the “light emitting unit” refers to a minimum unit that includes one or more organic layers, one of which is a light emitting layer, and can emit light by recombination of injected holes and electrons.
  • typical element configurations of simple organic EL elements include the following element configurations.
  • Anode / light emitting unit / cathode The above light emitting unit may be a laminated type having a plurality of phosphorescent light emitting layers and fluorescent light emitting layers. In that case, the light emitting unit is generated by a phosphorescent light emitting layer between the light emitting layers. In order to prevent the excitons from diffusing into the fluorescent light emitting layer, a space layer may be provided. A typical layer structure of the light emitting unit is shown below.
  • A Hole transport layer / light emitting layer (/ electron transport layer)
  • B Hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer (/ electron transport layer)
  • C Hole transport layer / phosphorescent layer / space layer / fluorescent layer (/ electron transport layer)
  • D Hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer / space layer / fluorescent light emitting layer (/ electron transport layer)
  • E Hole transport layer / first phosphorescent light emitting layer / space layer / second phosphorescent light emitting layer / space layer / fluorescent light emitting layer (/ electron transport layer)
  • F Hole transport layer / phosphorescent layer / space layer / first fluorescent layer / second fluorescent layer (/ electron transport layer)
  • G Hole transport layer / electron barrier layer / light emitting layer (/ electron transport layer)
  • H Hole transport layer / light emitting layer / hole barrier layer (
  • Each phosphorescent or fluorescent light-emitting layer may have a different emission color.
  • hole transport layer / first phosphorescent light emitting layer (red light emitting) / second phosphorescent light emitting layer (green light emitting) / space layer / fluorescent light emitting layer (blue light emitting) / Examples include a layer configuration such as an electron transport layer.
  • An electron barrier layer may be appropriately provided between each light emitting layer and the hole transport layer or space layer.
  • a hole blocking layer may be appropriately provided between each light emitting layer and the electron transport layer.
  • the following element structure can be mentioned as a typical element structure of a tandem type organic EL element.
  • the intermediate layer is generally called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, or an intermediate insulating layer, and has electrons in the first light emitting unit and holes in the second light emitting unit.
  • a known material structure to be supplied can be used.
  • FIG. 1 shows a schematic configuration of an example of the organic EL element of the present invention.
  • the organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and a light emitting unit 10 disposed between the anode 3 and the cathode 4.
  • the light emitting unit 10 includes a light emitting layer 5 including at least one layer including the first host material, the second host material, and the light emitting material.
  • a hole injection / transport layer 6 or the like may be formed between the light emitting layer 5 and the anode 3, and an electron injection / transport layer 7 or the like may be formed between the light emitting layer 5 and the cathode 4.
  • an electron barrier layer may be provided on the anode 3 side of the light emitting layer 5, and a hole barrier layer may be provided on the cathode 4 side of the light emitting layer 5.
  • a host combined with a fluorescent dopant is referred to as a fluorescent host
  • a host combined with a phosphorescent dopant is referred to as a phosphorescent host.
  • the fluorescent host and the phosphorescent host are not distinguished only by the molecular structure. That is, the phosphorescent host means a material constituting a phosphorescent light emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material constituting a fluorescent light emitting layer. The same applies to the fluorescent host.
  • the organic EL element of the present invention is produced on a translucent substrate.
  • the light-transmitting substrate is a substrate that supports the organic EL element, and is preferably a smooth substrate having a light transmittance in the visible region of 400 nm to 700 nm of 50% or more.
  • a glass plate, a polymer plate, etc. are mentioned.
  • the glass plate include those using soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz and the like as raw materials.
  • the polymer plate include those using polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, polysulfone and the like as raw materials.
  • the anode of the organic EL element plays a role of injecting holes into the hole transport layer or the light emitting layer, and it is effective to use a material having a work function of 4.5 eV or more.
  • Specific examples of the anode material include indium tin oxide alloy (ITO), tin oxide (NESA), indium zinc oxide, gold, silver, platinum, copper, and the like.
  • the anode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. When light emitted from the light emitting layer is extracted from the anode, it is preferable that the transmittance of light in the visible region of the anode is greater than 10%.
  • the sheet resistance of the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness of the anode depends on the material, but is usually selected in the range of 10 nm to 1 ⁇ m, preferably 10 nm to 200 nm.
  • the cathode plays a role of injecting electrons into the electron injection layer, the electron transport layer or the light emitting layer, and is preferably formed of a material having a small work function.
  • the cathode material is not particularly limited, and specifically, indium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-lithium alloy, aluminum-scandium-lithium alloy, magnesium-silver alloy and the like can be used.
  • the cathode can be produced by forming a thin film by a method such as vapor deposition or sputtering. Moreover, you may take out light emission from the cathode side as needed.
  • the light emitting layer is an organic layer having a light emitting function and is formed of one layer or a plurality of layers, and one of them contains the first host material, the second host material, and the light emitting material as described above.
  • the light emitting layer other than the above includes a host material and a dopant material when a doping system is employed.
  • the host material mainly has a function of encouraging recombination of electrons and holes and confining excitons in the light emitting layer, and the dopant material efficiently emits excitons obtained by recombination. It has a function.
  • the host material mainly has a function of confining excitons generated by the dopant in the light emitting layer.
  • the above light emitting layer may adopt a double dopant in which each dopant emits light by adding two or more kinds of dopant materials having a high quantum yield. Specifically, a mode in which yellow light emission is realized by co-evaporating a host, a red dopant, and a green dopant to make the light emitting layer common.
  • the above light-emitting layer is a laminate in which a plurality of light-emitting layers are stacked, so that electrons and holes are accumulated at the light-emitting layer interface, and the recombination region is concentrated at the light-emitting layer interface to improve quantum efficiency. Can do.
  • the ease of injecting holes into the light emitting layer may be different from the ease of injecting electrons, and the hole transport ability and electron transport ability expressed by the mobility of holes and electrons in the light emitting layer may be different. May be different.
  • a light emitting layer can be formed by well-known methods, such as a vapor deposition method, a spin coat method, LB method, for example.
  • the light emitting layer can also be formed by thinning a solution obtained by dissolving a binder such as a resin and a material compound in a solvent by a spin coating method or the like.
  • the light emitting layer is preferably a molecular deposited film.
  • the molecular deposited film is a thin film formed by deposition from a material compound in a gas phase state or a film formed by solidifying from a material compound in a solution state or a liquid phase state.
  • the thin film (molecular accumulation film) formed by the LB method can be classified by the difference in the aggregation structure and the higher-order structure, and the functional difference resulting therefrom.
  • the content ratio of the first host material and the second host material in the light emitting layer is not particularly limited and can be adjusted as appropriate.
  • the mass ratio of the first host material: second host material 1: 99 to 99: 1 Within the range, more preferably within the range of 10:90 to 90:10.
  • the phosphorescent dopant (phosphorescent material) that forms the light emitting layer is a compound that can emit light from the triplet excited state, and is not particularly limited as long as it emits light from the triplet excited state, but Ir, Pt, Os, Au, Cu, An organometallic complex containing at least one metal selected from Re and Ru and a ligand is preferable.
  • the ligand preferably has an ortho metal bond.
  • a metal complex containing a metal atom selected from Ir, Os and Pt is preferred in that the phosphorescent quantum yield is high and the external quantum efficiency of the light emitting device can be further improved.
  • iridium complexes and platinum complexes are more preferable, and orthometalated iridium complexes are particularly preferable.
  • the content of the phosphorescent dopant in the light emitting layer is not particularly limited and may be appropriately selected depending on the intended purpose. For example, it is preferably 0.1 to 70% by mass, more preferably 1 to 30% by mass. If the phosphorescent dopant content is 0.1% by mass or more, sufficient light emission can be obtained, and if it is 70% by mass or less, concentration quenching can be avoided.
  • a phosphorescent dopant material may be used independently and may use 2 or more types together.
  • the emission wavelength of the phosphorescent dopant material contained in the light emitting layer is not particularly limited, but at least one of the phosphorescent dopant materials contained in the light emitting layer preferably has a peak emission wavelength of 490 nm to 700 nm. More preferably, it is 650 nm or less.
  • the phosphorescent host is a compound having a function of efficiently emitting the phosphorescent dopant by efficiently confining the triplet energy of the phosphorescent dopant in the light emitting layer.
  • compounds other than the first host material and the second host material can be appropriately selected as a phosphorescent host according to the purpose.
  • the first host material and the second host material and other compounds may be used in combination as a phosphorescent host material in the same light emitting layer.
  • the first host material and the second host material may be used as the phosphorescent host material, and a compound other than the first host material or the second host material may be used as the phosphorescent host material of another light emitting layer.
  • the first host material and the second host material can also be used for organic layers other than the light emitting layer.
  • compounds other than the first host material and the second host material and suitable as a phosphorescent host include carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline.
  • pyrazolone derivatives phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidene compounds , Porphyrin compounds, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluoresceins Represented by metal complexes of redenemethane derivatives, distyrylpyrazine derivatives, heterocyclic tetracarboxylic anhydrides such as naphthaleneperylene, phthalocyanine derivatives, 8-quinolinol derivatives, metal phthalocyanines, metal complexes with benzo
  • the thickness of the light emitting layer is preferably 5 to 50 nm, more preferably 7 to 50 nm, and still more preferably 10 to 50 nm.
  • the thickness is 5 nm or more, it is easy to form a light emitting layer, and when the thickness is 50 nm or less, an increase in driving voltage can be avoided.
  • the organic EL device of the present invention preferably has an electron donating dopant in the interface region between the cathode and the light emitting unit. According to such a configuration, it is possible to improve the light emission luminance and extend the life of the organic EL element.
  • the electron donating dopant means a material containing a metal having a work function of 3.8 eV or less, and specific examples thereof include alkali metals, alkali metal complexes, alkali metal compounds, alkaline earth metals, alkaline earths. Examples thereof include at least one selected from metal complexes, alkaline earth metal compounds, rare earth metals, rare earth metal complexes, rare earth metal compounds, and the like.
  • alkali metal examples include Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV), Cs (work function: 1.95 eV), and the like.
  • a function of 2.9 eV or less is particularly preferable. Of these, K, Rb, and Cs are preferred, Rb and Cs are more preferred, and Cs is most preferred.
  • alkaline earth metals include Ca (work function: 2.9 eV), Sr (work function: 2.0 eV to 2.5 eV), Ba (work function: 2.52 eV), and the like. The thing below 9 eV is especially preferable.
  • rare earth metals examples include Sc, Y, Ce, Tb, Yb, and the like, and those having a work function of 2.9 eV or less are particularly preferable.
  • alkali metal compound examples include alkali oxides such as Li 2 O, Cs 2 O, and K 2 O, and alkali halides such as LiF, NaF, CsF, and KF, and LiF, Li 2 O, and NaF are preferable.
  • alkaline earth metal compound examples include BaO, SrO, CaO, and Ba x Sr 1-x O (0 ⁇ x ⁇ 1), Ba x Ca 1-x O (0 ⁇ x ⁇ 1) mixed with these. BaO, SrO, and CaO are preferable.
  • the rare earth metal compound, YbF 3, ScF 3, ScO 3, Y 2 O 3, Ce 2 O 3, GdF 3, TbF 3 and the like, YbF 3, ScF 3, TbF 3 are preferable.
  • the alkali metal complex, alkaline earth metal complex, and rare earth metal complex are not particularly limited as long as each metal ion contains at least one of an alkali metal ion, an alkaline earth metal ion, and a rare earth metal ion.
  • the ligand includes quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxydiaryl oxadiazole, hydroxydiaryl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxybenzotriazole, Hydroxyfulborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, ⁇ -diketones, azomethines, and derivatives thereof are preferred, but not limited thereto.
  • the electron donating dopant it is preferable to form a layered or island shape in the interface region.
  • a forming method while depositing an electron donating dopant by resistance heating vapor deposition, an organic compound (light emitting material or electron injecting material) that forms an interface region is simultaneously deposited, and the electron donating dopant is dispersed in the organic compound.
  • the electron donating dopant is formed in a layered form
  • the reducing dopant is vapor-deposited by a resistance heating vapor deposition method. .1 nm to 15 nm.
  • the electron donating dopant is formed in an island shape
  • the electron donating dopant is deposited by resistance heating vapor deposition alone, preferably The island is formed with a thickness of 0.05 nm to 1 nm.
  • the electron transport layer is an organic layer formed between the light emitting layer and the cathode, and has a function of transporting electrons from the cathode to the light emitting layer.
  • an organic layer close to the cathode may be defined as an electron injection layer.
  • the electron injection layer has a function of efficiently injecting electrons from the cathode into the organic layer unit.
  • an aromatic heterocyclic compound containing one or more heteroatoms in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferable.
  • the nitrogen-containing ring derivative is preferably an aromatic ring having a nitrogen-containing 6-membered ring or 5-membered ring skeleton, or a condensed aromatic ring compound having a nitrogen-containing 6-membered ring or 5-membered ring skeleton.
  • a nitrogen-containing ring metal chelate complex represented by the following formula (AA) is preferable.
  • R 2 to R 7 in formula (AA) are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, an amino group, a hydrocarbon group having 1 to 40 carbon atoms, or an alkoxy group having 1 to 40 carbon atoms.
  • Examples of the halogen atom include fluorine, chlorine, bromine, iodine and the like.
  • the amino group which may be substituted include an alkylamino group, an arylamino group and an aralkylamino group.
  • the alkylamino group and the aralkylamino group are represented as —NQ 1 Q 2 .
  • Q 1 and Q 2 each independently represents an alkyl group having 1 to 20 carbon atoms or an aralkyl group having 1 to 20 carbon atoms.
  • One of Q 1 and Q 2 may be a hydrogen atom or a deuterium atom.
  • the arylamino group is represented as —NAr 1 Ar 2, and Ar 1 and Ar 2 each independently represents a non-condensed aromatic hydrocarbon group or a condensed aromatic hydrocarbon group having 6 to 50 carbon atoms.
  • Ar 1 and Ar 2 may be a hydrogen atom or a deuterium atom.
  • the hydrocarbon group having 1 to 40 carbon atoms includes an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, and an aralkyl group.
  • the alkoxycarbonyl group is represented as —COOY ′, and Y ′ represents an alkyl group having 1 to 20 carbon atoms.
  • M in the formula (AA) is aluminum (Al), gallium (Ga), or indium (In), and is preferably In.
  • L in the formula (AA) is a group represented by the following formula (A ′) or (A ′′).
  • R 8 to R 12 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other are cyclic structures May be formed.
  • R 13 to R 27 are each independently a hydrogen atom, a deuterium atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other are An annular structure may be formed.
  • the hydrocarbon group having 1 to 40 carbon atoms represented by R 8 to R 12 and R 13 to R 27 in the formula (A ′) and the formula (A ′′) is represented by R 2 to R 7 in the formula (A).
  • the divalent group in the case where the adjacent groups of R 8 to R 12 and R 13 to R 27 form a cyclic structure includes a tetramethylene group, a pentamethylene group, a hexamethylene group, and the like. Examples include a methylene group, diphenylmethane-2,2′-diyl group, diphenylethane-3,3′-diyl group, and diphenylpropane-4,4′-diyl group.
  • 8-hydroxyquinoline or a metal complex of its derivative, an oxadiazole derivative, or a nitrogen-containing heterocyclic derivative is preferable.
  • a metal chelate oxinoid compound containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline) such as tris (8-quinolinol) aluminum is used.
  • 8-quinolinol or 8-hydroxyquinoline such as tris (8-quinolinol
  • oxadiazole derivative the following can be mentioned.
  • Ar 17 , Ar 18 , Ar 19 , Ar 21 , Ar 22 and Ar 25 each represent a substituted or unsubstituted aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 50 carbon atoms
  • Ar 17 and Ar 18 , Ar 19 and Ar 21 , Ar 22 and Ar 25 may be the same or different.
  • the aromatic hydrocarbon group or the condensed aromatic hydrocarbon group include a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a perylenyl group, and a pyrenyl group.
  • substituents include alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, and cyano groups.
  • Ar 20 , Ar 23, and Ar 24 each represent a substituted or unsubstituted divalent aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 50 carbon atoms, and Ar 23 and Ar 24 are identical to each other. But it can be different.
  • the divalent aromatic hydrocarbon group or condensed aromatic hydrocarbon group include a phenylene group, a naphthylene group, a biphenylene group, an anthranylene group, a peryleneylene group, and a pyrenylene group.
  • substituents include alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, and cyano groups.
  • electron transfer compounds those having good thin film forming properties are preferably used.
  • Specific examples of these electron transfer compounds include the following.
  • the nitrogen-containing heterocyclic derivative as the electron transfer compound is a nitrogen-containing heterocyclic derivative composed of an organic compound having the following formula, and includes a nitrogen-containing compound that is not a metal complex. Examples thereof include a 5-membered ring or 6-membered ring containing a skeleton represented by the following formula (B) and a structure represented by the following formula (C).
  • X represents a carbon atom or a nitrogen atom.
  • Z 1 and Z 2 each independently represents an atomic group capable of forming a nitrogen-containing heterocycle.
  • the nitrogen-containing heterocyclic derivative is more preferably an organic compound having a nitrogen-containing aromatic polycyclic group consisting of a 5-membered ring or a 6-membered ring. Further, in the case of such a nitrogen-containing aromatic polycyclic group having a plurality of nitrogen atoms, the nitrogen-containing compound having a skeleton in which the above formulas (B) and (C) or the above formula (B) and the following formula (D) are combined. Aromatic polycyclic organic compounds are preferred.
  • the nitrogen-containing group of the nitrogen-containing aromatic polycyclic organic compound is selected from, for example, nitrogen-containing heterocyclic groups represented by the following formulae.
  • R is an aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 40 carbon atoms, an aromatic heterocyclic group or condensed aromatic heterocyclic group having 3 to 40 carbon atoms, 1 to 20 is an alkyl group or an alkoxy group having 1 to 20 carbon atoms, n is an integer of 0 to 5, and when n is an integer of 2 or more, a plurality of R may be the same or different from each other.
  • preferred specific compounds include nitrogen-containing heterocyclic derivatives represented by the following formula (D1). HAr-L 1 -Ar 1 -Ar 2 (D1)
  • HAr is a substituted or unsubstituted nitrogen-containing heterocyclic group having 3 to 40 carbon atoms
  • L 1 is a single bond, substituted or unsubstituted aromatic hydrocarbon having 6 to 40 carbon atoms.
  • Ar 1 is a substituted or unsubstituted 2 to 6 carbon atom having 2 to 6 carbon atoms.
  • Ar 2 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 carbon atoms, a condensed aromatic hydrocarbon group, or a substituted or unsubstituted aromatic group having 3 to 40 carbon atoms. It is a heterocyclic group or a condensed aromatic heterocyclic group.
  • HAr in the formula (D1) is selected from the following group, for example.
  • L 1 in the formula (D1) is selected from the following group, for example.
  • Ar 1 in the formula (D1) is selected from, for example, arylanthranyl groups of the following formulas (D2) and (D3).
  • R 1 to R 14 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, or an alkoxy having 1 to 20 carbon atoms.
  • R 1 to R 8 may be nitrogen-containing heterocyclic derivatives each of which is a hydrogen atom or a deuterium atom.
  • Ar 2 in the formula (D1) is selected from the following group, for example.
  • the following compounds are also preferably used as the nitrogen-containing aromatic polycyclic organic compound as the electron transporting compound.
  • R 1 to R 4 each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted aliphatic group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon number of 3 to 20
  • X 1 and X 2 are each independently Represents an oxygen atom, a sulfur atom, or a dicyanomethylene group.
  • the following compounds are also preferably used as the electron transfer compound.
  • R 1 , R 2 , R 3 and R 4 are the same or different groups, and are an aromatic hydrocarbon group or a condensed aromatic hydrocarbon group represented by the following formula (D6) It is.
  • R 5 , R 6 , R 7 , R 8 and R 9 are the same or different from each other, and are a hydrogen atom, a deuterium atom, a saturated or unsaturated alkoxy group having 1 to 20 carbon atoms.
  • At least one of R 5 , R 6 , R 7 , R 8 and R 9 is a group other than a hydrogen atom or a deuterium atom.
  • the electron transfer compound may be a polymer compound containing the nitrogen-containing heterocyclic group or the nitrogen-containing heterocyclic derivative.
  • the electron transport layer of the organic EL device of the present invention particularly preferably contains at least one nitrogen-containing heterocyclic derivative represented by the following formulas (E) to (G).
  • Z 1 , Z 2, and Z 3 are each independently a nitrogen atom or a carbon atom.
  • R 1 and R 2 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, substituted or unsubstituted carbon An alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
  • n is an integer of 0 to 5, and when n is an integer of 2 or more, the plurality of R 1 may be the same or different from each other. Further, two adjacent R 1 's may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring.
  • Ar 1 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
  • Ar 2 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted Alternatively, it is an unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
  • Ar 1 or Ar 2 is a substituted or unsubstituted condensed aromatic hydrocarbon ring group having 10 to 50 ring carbon atoms or a substituted or unsubstituted condensed aromatic group having 9 to 50 ring atoms. It is a heterocyclic group.
  • Ar 3 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 50 ring atoms.
  • L 1 , L 2 and L 3 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a divalent or substituted or unsubstituted divalent atom having 9 to 50 ring atoms.
  • aryl group having 6 to 50 ring carbon atoms examples include phenyl group, naphthyl group, anthryl group, phenanthryl group, naphthacenyl group, chrysenyl group, pyrenyl group, biphenyl group, terphenyl group, tolyl group, fluoranthenyl group, fluorenyl Groups and the like.
  • heteroaryl groups having 5 to 50 ring atoms include pyrrolyl, furyl, thienyl, silolyl, pyridyl, quinolyl, isoquinolyl, benzofuryl, imidazolyl, pyrimidyl, carbazolyl, selenophenyl Group, oxadiazolyl group, triazolyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinoxalinyl group, acridinyl group, imidazo [1,2-a] pyridinyl group, imidazo [1,2-a] pyrimidinyl group and the like.
  • Examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group.
  • Examples of the haloalkyl group having 1 to 20 carbon atoms include groups obtained by substituting one or more hydrogen atoms of the alkyl group with at least one halogen atom selected from fluorine, chlorine, iodine and bromine.
  • Examples of the alkoxy group having 1 to 20 carbon atoms include groups having the above alkyl group as an alkyl moiety.
  • Examples of the arylene group having 6 to 50 ring carbon atoms include groups obtained by removing one hydrogen atom from the aryl group.
  • Examples of the divalent condensed aromatic heterocyclic group having 9 to 50 ring atoms include groups obtained by removing one hydrogen atom from the condensed aromatic heterocyclic group described as the heteroaryl group.
  • the thickness of the electron transport layer is not particularly limited, but is preferably 1 nm to 100 nm. Moreover, it is preferable to use an insulator or a semiconductor as an inorganic compound in addition to the nitrogen-containing ring derivative as a component of the electron injection layer that can be provided adjacent to the electron transport layer. If the electron injection layer is made of an insulator or a semiconductor, current leakage can be effectively prevented and the electron injection property can be improved.
  • an insulator it is preferable to use at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides. If the electron injection layer is composed of these alkali metal chalcogenides or the like, it is preferable in that the electron injection property can be further improved.
  • preferable alkali metal chalcogenides include, for example, Li 2 O, K 2 O, Na 2 S, Na 2 Se, and Na 2 O
  • preferable alkaline earth metal chalcogenides include, for example, CaO, BaO. , SrO, BeO, BaS and CaSe.
  • preferable alkali metal halides include, for example, LiF, NaF, KF, LiCl, KCl, and NaCl.
  • preferable alkaline earth metal halides include fluorides such as CaF 2 , BaF 2 , SrF 2 , MgF 2 and BeF 2 , and halides other than fluorides.
  • the inorganic compound constituting the electron injection layer is preferably a microcrystalline or amorphous insulating thin film. If the electron injection layer is composed of these insulating thin films, a more uniform thin film is formed, and pixel defects such as dark spots can be reduced. Examples of such inorganic compounds include alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides.
  • the preferred thickness of the layer is about 0.1 nm to 15 nm.
  • the electron injection layer in the present invention is preferable even if it contains the above-mentioned electron donating dopant.
  • an organic layer close to the anode may be defined as a hole injection layer.
  • the hole injection layer has a function of efficiently injecting holes from the anode into the organic layer unit.
  • an aromatic amine compound for example, an aromatic amine derivative represented by the following formula (H) is preferably used.
  • Ar 1 to Ar 4 represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a condensed aromatic hydrocarbon group, a substituted or unsubstituted ring forming atom number of 5 to 50 aromatic heterocyclic groups or condensed aromatic heterocyclic groups, or a group in which these aromatic hydrocarbon groups or condensed aromatic hydrocarbon groups and aromatic heterocyclic groups or condensed aromatic heterocyclic groups are bonded.
  • L represents a substituted or unsubstituted aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring forming atom number of 5 to 50. Represents an aromatic heterocyclic group or a condensed aromatic heterocyclic group.
  • An aromatic amine represented by the following formula (J) is also preferably used for forming the hole transport layer.
  • the hole transport layer of the organic EL device of the present invention may have a two-layer structure of a first hole transport layer (anode side) and a second hole transport layer (cathode side).
  • the thickness of the hole transport layer is not particularly limited, but is preferably 10 to 200 nm.
  • a layer containing an acceptor material may be bonded to the anode side of the hole transport layer or the first hole transport layer. This is expected to reduce drive voltage and manufacturing costs.
  • the acceptor material a compound represented by the following formula (K) is preferable.
  • R 21 to R 26 may be the same as or different from each other, and are each independently a cyano group, —CONH 2 , carboxyl group, or —COOR 27 (R 27 is a group having 1 to 20 carbon atoms) Represents an alkyl group or a cycloalkyl group having 3 to 20 carbon atoms, provided that one or more pairs of R 21 and R 22 , R 23 and R 24 , and R 25 and R 26 are combined together.
  • a group represented by —CO—O—CO— may be formed.
  • R 27 examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.
  • the thickness of the layer containing the acceptor material is not particularly limited, but is preferably 5 to 20 nm.
  • n doping is a method of doping a metal such as Li or Cs into an electron transport material
  • p doping is F 4 TCNQ (2, 3, 5, 6) as a hole transport material.
  • the space layer is a fluorescent layer for the purpose of adjusting the carrier balance so that excitons generated in the phosphorescent layer are not diffused into the fluorescent layer. It is a layer provided between the layer and the phosphorescent light emitting layer.
  • the space layer can be provided between the plurality of phosphorescent light emitting layers. Since the space layer is provided between the light emitting layers, a material having both electron transport properties and hole transport properties is preferable. In order to prevent diffusion of triplet energy in the adjacent phosphorescent light emitting layer, the triplet energy is preferably 2.6 eV or more. Examples of the material used for the space layer include the same materials as those used for the above-described hole transport layer.
  • the organic EL device of the present invention preferably has a barrier layer such as an electron barrier layer, a hole barrier layer, or a triplet barrier layer in a portion adjacent to the light emitting layer.
  • the electron barrier layer is a layer that prevents electrons from leaking from the light emitting layer to the hole transport layer
  • the hole barrier layer is a layer that prevents holes from leaking from the light emitting layer to the electron transport layer. is there.
  • the triplet barrier layer prevents the triplet excitons generated in the light emitting layer from diffusing into the surrounding layers, and confins the triplet excitons in the light emitting layer, thereby transporting electrons other than the light emitting dopant of the triplet excitons.
  • the energy difference ⁇ E T is preferably as large as possible relative to the thermal energy at room temperature, more preferably 0.1 eV or more, and particularly preferably 0.2 eV or more.
  • the electron mobility of the material constituting the triplet barrier layer is preferably 10 ⁇ 6 cm 2 / Vs or more in the range of the electric field strength of 0.04 to 0.5 MV / cm.
  • the electron mobility is determined by impedance spectroscopy.
  • the electron injection layer is desirably 10 ⁇ 6 cm 2 / Vs or more in the range of electric field strength of 0.04 to 0.5 MV / cm. This facilitates the injection of electrons from the cathode into the electron transport layer, and also promotes the injection of electrons into the adjacent barrier layer and the light emitting layer, thereby enabling driving at a lower voltage.
  • intermediate 1 (6.6 g, 23.7 mmol), triphenylphosphine (15.6 g, 59.3 mmol), and o-dichlorobenzene (24 mL) were sequentially added and heated at 180 ° C. for 8 hours.
  • the reaction solution was cooled to room temperature and then purified by silica gel column chromatography to obtain Intermediate 2 (4 g, yield 68%).
  • the intermediate body 2 was identified by analysis of FD-MS (field desorption mass spectrum).
  • Intermediate 1 In the synthesis of Intermediate 1, intermediate 2 was used instead of 2-nitro-1,4-dibromobenzene, and 9-phenylcarbazol-3-ylboronic acid was used instead of phenylboronic acid. .
  • the powder was identified as Intermediate 3 by FD-MS (field desorption mass spectrum) analysis.
  • intermediate 3 (1.6 g, 3.9 mmol), 4-bromobenzonitrile (0.71 g, 3.9 mmol), tris (dibenzylideneacetone) dipalladium (0.071 g, 0.078 mmol), Tri-t-butylphosphonium tetrafluoroborate (0.091 g, 0.31 mmol), t-butoxy sodium (0.53 g, 5.5 mmol), and anhydrous toluene (20 mL) were sequentially added, and the mixture was heated to reflux for 8 hours. After cooling the reaction solution to room temperature, the organic layer was separated, and the organic solvent was distilled off under reduced pressure.
  • the compound H1 was synthesized in the same manner using 4′-bromobiphenyl-3-carbonitrile instead of 4-bromobenzonitrile.
  • FD-MS field desorption mass spectrum
  • UV ultraviolet absorption maximum wavelength
  • FL fluorescence emission maximum wavelength
  • the compound H1 was synthesized in the same manner using 4′-bromobiphenyl-4-carbonitrile instead of 4-bromobenzonitrile.
  • FD-MS field desorption mass spectrum
  • UV (PhMe) ultraviolet absorption maximum wavelength
  • ⁇ max ultraviolet absorption maximum wavelength
  • UV (PhMe) fluorescence emission maximum wavelength
  • ⁇ max UV absorption maximum wavelength
  • the compound H1 was synthesized in the same manner using 3′-bromobiphenyl-4-carbonitrile instead of 4-bromobenzonitrile.
  • FD-MS field desorption mass spectrum
  • UV ultraviolet absorption maximum wavelength
  • FL fluorescence emission maximum wavelength
  • Synthesis Example 15 Synthesis of Compound H15
  • the compound H1 was synthesized in the same manner using 2-bromo-8-cyanodibenzofuran instead of 4-bromobenzonitrile.
  • FD-MS field desorption mass spectrum of the obtained compound is shown below.
  • Example 1 Manufacture of organic EL elements
  • a glass substrate with an ITO transparent electrode of 25 mm ⁇ 75 mm ⁇ thickness 1.1 mm (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes.
  • the glass substrate with the transparent electrode line after washing is mounted on the substrate holder of the vacuum deposition apparatus, and the following electron-accepting (acceptor) compound is first formed so as to cover the transparent electrode on the surface on which the transparent electrode line is formed.
  • C-1 was vapor-deposited to form a compound C-1 film having a thickness of 5 nm.
  • the following aromatic amine derivative (Compound X1) was deposited as a first hole transport material to form a first hole transport layer having a thickness of 65 nm.
  • the following aromatic amine derivative (Compound X2) was deposited as a second hole transport material to form a second hole transport layer having a thickness of 10 nm.
  • the host material 1 and the host material 2 described in Table 1 below as the host material and the following compound Ir (bzq) 3 as the phosphorescent material are co-evaporated, and the film thickness is 25 nm.
  • a phosphorescent light emitting layer was formed.
  • the concentration of the compound Ir (bzq) 3 in the light emitting layer was 10.0% by mass, the concentration of the host material 1 was 45.0% by mass, and the concentration of the host material 2 was 45.0% by mass.
  • This co-deposited film functions as a light emitting layer.
  • the following compound ET was formed to a thickness of 35 nm.
  • This compound ET film functions as an electron transport layer.
  • LiF was used as an electron injecting electrode (cathode), and the film thickness was set to 1 nm at a film forming rate of 0.1 angstrom / min.
  • Metal Al was vapor-deposited on this LiF film, and a metal cathode was formed with a film thickness of 80 nm to produce an organic EL device.
  • the compounds used in Examples and Comparative Examples are shown below.
  • Luminous efficiency of the obtained organic EL device was measured at room temperature and DC constant current drive (current density 1 mA / cm 2 ). Further, an 80% lifetime (time until the luminance is reduced to 80% of the initial luminance by constant current driving) at an initial luminance of 10,000 cd / m 2 was obtained. The results are shown in Table 1.
  • Examples 2 to 5 and Comparative Example 1 An organic EL element was produced in the same manner as in Example 1 except that the light emitting layer was formed using the host material 1 and the host material 2 shown in Table 2 as the host material of the light emitting layer. Table 1 shows the results of luminous efficiency and 80% lifetime of the obtained organic EL device.
  • the light emitting layer is obtained by combining the compounds H1 and H3 to H5 which are the first host materials represented by the formula (A) and the compound F2 or F3 which is the second host material represented by the formula (1).
  • the organic EL elements of Examples 1 to 5 used as the host material (cohost) of Example 1 had good luminous efficiency. Furthermore, the organic EL devices of Examples 1 to 5 have a longer lifetime than the organic EL devices of Comparative Example 1 using the same central skeleton but the compound F1 and the compound F3, which are not substituted with cyano groups at the ends, as cohosts. It was converted.
  • Example 6 Manufacture of organic EL elements
  • a glass substrate manufactured by Geomatic Co., Ltd.
  • a transparent electrode anode, 70 nm
  • the cleaned glass substrate with a transparent electrode line is mounted on a substrate holder of a vacuum deposition apparatus, and the compound electrode C is formed by resistance heating vapor deposition so as to cover the transparent electrode on the surface on which the transparent electrode line is formed. -1 was laminated.
  • a hole injection layer adjacent to the anode having a thickness of 10 nm was formed.
  • compound X4 was laminated by resistance heating vapor deposition. This formed the 65-nm-thick 1st positive hole transport layer.
  • the compound X3 was laminated
  • a second hole transport layer having a thickness of 10 nm was formed.
  • compound H5 as the first host material, compound F2 as the second host material, and Ir (bzq) 3 as the phosphorescent dopant were co-evaporated by resistance heating. This formed the 25-nm-thick light emitting layer which shows yellow light emission.
  • concentration of the 1st host material in the light emitting layer, the 2nd host material, and the luminescent dopant was 45 mass%, 45 mass%, and 10 mass%, respectively.
  • the compound ET was laminated
  • Examples 7 to 17 and Comparative Examples 3 and 6 to 7 An organic EL device was produced in the same manner as in Example 6 except that the light emitting layer was formed using the host material 1 and the host material 2 shown in Table 2 as the host material of the light emitting layer. Table 2 shows the results of the voltage, luminous efficiency, and 90% lifetime of the obtained organic EL device.
  • Comparative Examples 2, 4 and 5 An organic EL device was produced in the same manner as in Example 6 except that the light emitting layer was formed using the host material 2 (90% by mass) shown in Table 2 as the host material of the light emitting layer. Table 2 shows the results of the voltage, luminous efficiency, and 90% lifetime of the obtained organic EL device.
  • Example 18 Manufacture of organic EL elements
  • a glass substrate manufactured by Geomatic Co., Ltd.
  • a transparent ITO electrode anode, 130 nm
  • UV ozone cleaning for 30 minutes. It was.
  • the cleaned glass substrate with a transparent electrode line is mounted on a substrate holder of a vacuum deposition apparatus, and the compound electrode C is formed by resistance heating vapor deposition so as to cover the transparent electrode on the surface on which the transparent electrode line is formed.
  • -1 was laminated. This formed a hole injection layer adjacent to the 5 nm thick anode.
  • compound X1 was laminated by resistance heating vapor deposition.
  • a first hole transport layer having a thickness of 160 nm was formed.
  • the compound X3 was laminated
  • a second hole transport layer having a thickness of 10 nm was formed.
  • compound H5 as the first host material, compound F2 as the second host material, and Ir (ppy) 3 as the phosphorescent dopant were co-deposited by resistance heating.
  • a light emitting layer having a thickness of 25 nm and emitting green light was formed.
  • concentration of the 1st host material in the light emitting layer, the 2nd host material, and the luminescent dopant was 45 mass%, 45 mass%, and 10 mass%, respectively.
  • the compound ET was laminated
  • Examples 19 to 20 and Comparative Example 8 An organic EL device was produced in the same manner as in Example 18 except that the light emitting layer was formed using the host material 1 and the host material 2 shown in Table 3 as the host material of the light emitting layer. Table 3 shows the results of the voltage, external quantum efficiency, and 95% lifetime of the obtained organic EL device.
  • the organic EL elements of Examples 18 to 20 using the compound represented by the formula (A) as the first host material and the compound represented by the formula (1) as the second host material are the organic EL elements of Comparative Example 8.
  • the lifetime is longer than that of the EL element.
  • Examples 21 to 28 and Comparative Examples 9 to 11 An organic EL device was produced in the same manner as in Example 1 except that the light emitting layer was formed using the host material 1 and the host material 2 shown in Table 4 as the host material of the light emitting layer. Table 4 shows the results of the luminous efficiency and 90% lifetime of the obtained organic EL device.
  • Examples 29 to 35 and Comparative Examples 12 to 14 An organic EL device was produced in the same manner as in Example 18 except that the light emitting layer was formed using the host material 1 and the host material 2 shown in Table 5 as the host material of the light emitting layer. Table 5 shows the results of the voltage, external quantum efficiency, and 95% lifetime of the obtained organic EL device.
  • the organic EL device of the present invention has a good long-life performance.

Abstract

L'invention concerne un élément électroluminescent organique qui est caractérisé par : l'utilisation, comme premier hôte, d'un dérivé biscarbazole qui a une structure spécifique ayant un groupe cyano ; et l'utilisation, comme second hôte, d'un composé qui a à la fois une structure de dérivé carbazole et un noyau hétéroaromatique contenant de l'azote. Cet élément électroluminescent organique a une longue durée de vie de service.
PCT/JP2013/053767 2012-03-30 2013-02-15 Élément électroluminescent organique WO2013145923A1 (fr)

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JP2012-083145 2012-03-30
JP2012083145 2012-03-30
JPPCT/JP2012/081382 2012-12-04
PCT/JP2012/081382 WO2013084885A1 (fr) 2011-12-05 2012-12-04 Élément électroluminescent organique
US13/760,928 US9530969B2 (en) 2011-12-05 2013-02-06 Material for organic electroluminescence device and organic electroluminescence device
US13/760,928 2013-02-06

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WO2015060352A1 (fr) * 2013-10-24 2015-04-30 出光興産株式会社 Élément électroluminescent organique et dispositif électronique
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