WO2005057987A1 - 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 - Google Patents
有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 Download PDFInfo
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- WO2005057987A1 WO2005057987A1 PCT/JP2004/018960 JP2004018960W WO2005057987A1 WO 2005057987 A1 WO2005057987 A1 WO 2005057987A1 JP 2004018960 W JP2004018960 W JP 2004018960W WO 2005057987 A1 WO2005057987 A1 WO 2005057987A1
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- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical group C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical group C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
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Definitions
- the present invention relates to an organic electroluminescent element material and an organic electroluminescent element using the same, and in particular, has high luminous efficiency, has no pixel defects, has excellent heat resistance, and has a long life.
- the present invention relates to a material for an organic electroluminescence device and an organic electroluminescence device. Background art
- An organic electroluminescence element (hereinafter sometimes abbreviated as EL) may be formed by applying an electric field to the hole injected from the anode and the hole injected from the cathode.
- EL organic electroluminescence element
- This is a self-luminous element that uses the principle that a fluorescent substance emits light by the recombination energy of the electrons.
- Eastman's Kodak C.W.Tang et al. Report on low-voltage driven organic EL devices using stacked devices (C.W.
- the device structure of the organic EL device as shown in this example is a two-layer type of a hole transport (injection) layer and an electron transport / emission layer, or a hole transport (Note: T layer, emission layer, electron transport (injection)
- T layer, emission layer, electron transport (injection) The three-layer structure is well known, etc.
- the device structure and the forming method are devised in order to increase the recombination efficiency of injected holes and electrons.
- Light emitting materials for organic EL devices include chelate complexes such as tris (8-quinolinolato) aluminum complex, coumarin derivatives, terephthaline butadiene derivatives, distyryl arylene derivatives, and oxaziazoles.
- Light emitting materials such as derivatives are known, and it has been reported that they can emit light in the visible region from blue to red, and it is expected that a color display element will be realized (for example, see Patent Reference 1, Patent Document 2, Patent Document 3, etc.).
- Non-Patent Documents 1 and 2 it has been proposed to use a phosphorescent material in addition to a fluorescent material in the light emitting layer of an organic EL device (for example, see Non-Patent Documents 1 and 2).
- high luminous efficiency is achieved by utilizing the singlet state and triplet state of the excited state of the organic phosphor material in the light emitting layer of the organic EL device.
- electrons and holes recombine in the organic EL device, it is thought that singlet excitons and triplet excitons are produced in a ratio of 1: 3 due to the difference in spin multiplicity.
- the use of fluorescent light-emitting materials can achieve luminous efficiency 3 to 4 times that of devices using only fluorescence.
- an anode, a hole transport layer, an organic light emitting layer, and an electron transport layer (hole blocking layer) are sequentially arranged so that a triplet excited state or a triplet exciton is not quenched.
- Electron transport layer, cathode A configuration in which layers are stacked has been used, and a host compound and a phosphorescent compound have been used for the organic light emitting layer (for example, see Patent Documents 4 and 5).
- 4,4-N, N-dicarnozone rebiphenyl is used as a host compound, but this compound has a glass transition temperature of 1 ⁇ ⁇ 3 ⁇ 4 ′ or less and is roughly symmetric. There is a problem that crystallization is easy due to too good a property, and a short circuit or pixel defect occurs when a heat resistance test of the device is performed.
- Patent Document 6 Patent Document 7, Patent Document 8, etc.
- Patent Document 7 discloses a host material in which a heterocyclic skeleton such as a triazine skeleton is introduced in addition to a carpazole skeleton.
- Patent Document 9 discloses a compound in which a group having five or more benzene rings is bonded to a carbazole skeleton. However, this compound has high skeleton symmetry, is easily crystallized, and has five benzene rings. Because of the high linearity of the group having a benzene ring, there is a problem that the energy of the triplet excited state is reduced.
- Patent Document 1 Japanese Patent Application Laid-Open No. H8-2396955
- Patent Document 2 Japanese Unexamined Patent Application Publication No. Hei 7-138585
- Patent Document 3 Japanese Unexamined Patent Application Publication No. Hei 3-20289
- Patent Document 4 U.S. Patent No. 6,097,14 No. 7
- Patent Document 5 International Publication WO 0 1/4 15 12 No. '[Patent Document 6] Japanese Patent Application Laid-Open No. 2000-313131
- Patent Document 7 Japanese Patent Application Laid-Open No. 2 0 0 2 — 1 9 3 9 5 2 Publication
- Patent Document 8 EP 1 2 0 2.6 08 Specification
- Patent Document 9 Japanese Patent Laid-Open No. 2001-3113179
- Non-Patent Document 1 D.F.O'Brien and M.A.Baldo et al "
- Non-Patent Document 2 M. A. Baldo et al "Very high-efficiency green organic light-emitting devices based on electr o hosphorescence Applied Physics letters Vol. 75 No. 1, pp4-6, July 5, 1999 Disclosure of the invention
- An object of the present invention is to provide a material for an organic EL device having high luminous efficiency, no pixel defects, excellent heat resistance, and long life, and an organic EL device using the same. To provide With the goal.
- the present inventors have conducted intensive studies to achieve the above object, and as a result, by using a compound having a large molecular weight and low symmetry as a host material, high efficiency and high heat resistance have been achieved. They found that an organic EL device having a long service life could be obtained, and the present invention was solved.
- the present invention provides a material for an organic EL device comprising a compound represented by any of the following general formulas (1) to (3).
- R to R 3 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 40 carbon atoms which may have a substituent, or a carbon atom which may have a substituent.
- X is a group represented by any of the following general formulas (4) to (9).
- R 4 to R 13 ′ each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 40 carbon atoms which may have a substituent, or a substituent.
- Y i to Y 3 are each independently 7 to 2 CR (R is a hydrogen atom, a group bonded to X in the above general formulas (1) to (3), or R 4 , R 5 , R 6 , R 8, R 9 ,.) Or a nitrogen atom, and when it is a nitrogen atom, the number is at least two in the same ring.
- C z is the same as below.
- t is an integer of 0 to 1.
- C z is a group represented by the following general formula (10) or (11).
- R 4 ⁇ R 2. are their respective Independently has a hydrogen atom, a halogen atom, an alkyl group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group having 3 to 30 carbon atoms which may have a substituent, and a substituent.
- Z represents an alkyl group having 1 to 20 carbon atoms which may be substituted, an aryl group having 6 to 18 carbon atoms which may be substituted, or an aryl group having 7 to 40 carbon atoms which may have a substituent. Represents an aralkyl group.
- the present invention provides an organic EL device having at least one organic thin film layer having at least a light emitting layer sandwiched between a cathode and an anode, wherein at least one of the organic thin film layers is
- An object of the present invention is to provide an organic EL device containing a material for an organic EL device.
- an organic electroluminescent device comprising a compound represented by any of the general formulas (1) to (3) of the present invention provides high luminous efficiency, no pixel defects, and heat resistance.
- An organic electroluminescent element having excellent durability and a long life can be obtained.
- the organic electroluminescent device of the present invention is extremely useful as a light source for various electronic devices.
- the material for an organic EL device of the present invention comprises a compound represented by any one of the following general formulas (1) to (3).
- R! Rs each independently represents a hydrogen atom, a halogen atom, or a carbon atom having 1 to 40 carbon atoms (preferably having 1 to 40 carbon atoms).
- R! R! R! R! Rs each independently represents a hydrogen atom, a halogen atom, or a carbon atom having 1 to 40 carbon atoms (preferably having 1 to 40 carbon atoms).
- An alkoxy group having 40 (preferably 1 to 30 carbon atoms), an aryl group having 6 to 40 (preferably 6 to 30 carbon atoms) which may have a substituent, an aryloxy group having 6 to 40 carbon atoms (preferably 6 to 30 carbon atoms) which may have a group, or 7 to 40 carbon atoms (preferably having 6 to 30 carbon atoms) An aralkyl group having 7 to 30 carbon atoms, an alkenyl group having 2 to 40 carbon atoms (preferably having 2 to 30 carbon atoms) which may have a substituent, and a carbon atom optionally having a substituent.
- Numbers 1 to 80 (preferably carbon An alkylamino group having 1 to 60) or an arylamino group having 6 to 80 carbon atoms (preferably having 6 to 60 carbon atoms) which may have a substituent; Aralkylamino group having a good carbon number of 7 to 80 (preferably 7 to 60), and a carbon number of 3 to 10 (preferably 3 to 9) which may have a substituent. Or an arylsilyl group having 6 to 30 carbon atoms (preferably having 8 to 20 carbon atoms) or a cyano group which may have a substituent.
- R and R 3 may each be plural, and adjacent ones may form a saturated or unsaturated cyclic structure.
- halogen atoms for R 1 to R 3 include fluorine, chlorine, bromine, and iodine.
- Examples of the optionally substituted alkyl group having 1 to 40 carbon atoms for R i R s include a methyl group, an ethyl group, a propyl group, and an isoprene group. Mouth pill group, n-butyl group, s_butyl group, isobutyl group, butylinole group, n—pentynole group, n—hexynole group, n—heptinole group, n-octynole group, n—noninole group, n —Desinole group, n —Pindecinole group, n —Dodecyl group, n—Tridecyl group, n —Tetradecyl group, n —Pentadecyl group, n —Hexadecyl, n —Heptadecyl group, n-octadecinole group, Neopen
- ⁇ Dibu ⁇ -moethyl group 1,3-dibromoisopropyl group, 2,3-dibromo-t-butynole group, 1,2,3-tribromopropyl group, a-methinole group, 1-iodoethyl group , 2 — iodoethyl group, 2
- 2,3-tri-dope pill group aminomethyl group, 1-aminoethyl group 2-aminoethyl group, 2-aminobutyl group, 1,2-diamine, , Noethyl group, 1,3-diamino isopropyl group, 2, 3-diazine, no-t -butyl group, 1, 2, 3-triaminopropyl group, cyanomethyl group, 1- Cyanoethyl, 2 — cyanoethyl, 2 —Cyanisobutyl group, 1, 2 —Dicyanoethyl group, 1,3 —Dicyanoisopropyl group, 2,3 —Dicyano-t-butyl group, 1,2,3 — Tricyanopropyl group, nitrome Tyl, 1-nitroethyl, 2-diethyl, 1,2-dinitroethyl, 2,3—dinitro-t-butyl, 1, '2,3—trini Examples thereof include
- methyl, ethyl, propyl, isopropynole, n-butyl, s-butyl, isoptinole, t-butynole, n-pentyl, n-hexyl are preferred.
- N heptinole group, n — octyl group, n — noninole group, n — decyl group, 'n — pendyl group, n — dodecyl group, n — tridecyl group, n — tetradecinole group, 11 _ Pentadecyl group, n—hexadecyl group, n—heptadecinole group, n—octadecinole group, neopentyl group, 1—methinolepentinole group, 1-pentinolehexynole group, 1-pentynolepentynole group, 1-one Heptinoloctynole group, cyclohexanol group, cyclooctyl group, 3,5-tetramethylcyclohexyl group and the like.
- heterocyclic group having 3 to 30 carbon atoms which may have a substituent of R i Ra include, for example, 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group , Virazinyl group, 2-pyridinyl group, 1-imidazolyl group, 2-imidazolyl group, 1-birazolyl group, 1-indridinyl group, 2-indridinyl group, 3-a Pyridine, 5 pyridine, 6 pyridine, 7 pyridine, 8 phenyl, 2 imidazopyridinyl, 3 imi Dazopyridyl group, 5—imidazopyridinyl group, 6—imidazopyridinyl group, 7—imidazopyridinyl group, 8—imidazopyridinyl group, 3-monopyridinyl group, 4—pyridinyl group, 1—In drill base, 2—A Indolyl group, 3—indrill group, 41-indrill group,
- 3 Cheul group, 2 —Methylpyrroyl-1-yl group, 2 —Methylpyrroyl group 3 —Hyno group, 2 —Methynolepyrroyl / Lyi group, 2 —Methylnopyrroyl group 5 — A Nore group, 3 —methylpyrrole 1-inole group 3 1-Methylpyrroyl 1 2 —yl group, 3 —methylpyrrole 1 4 —yinole group, 3 —Methylpyrroyl 5 —yl group, 2 — t —Butylpyrroyl-1-yl group, 3- (2-phenyl-2-propyl) pyrrole-111-inole group, 2-methyl-1-indolinolate group, 4-methyl-11-indoleyl group, 2 —Methyl-3 —indole group, 4 —Methyl-3 —indolinole group, 2 — t —butyno
- the alkoxy group having 1 to 40 carbon atoms which may have a substituent of R i R a is a group represented by OY, and specific examples of Y are described in the above alkyl group. Similar ones are mentioned, as are the preferred examples.
- Examples of the aryl group having 6 to 40 carbon atoms which may have a substituent of R.iRs include, for example, phenyl group, 1.1-naphthyl group, 2-naphthyl group, and Entryl group, 2—anthrinole group, 9—anthryl group, 1 1 phenanthryl group, 2—phenanthryl group, 3—phenanthryl group, 4 1 Phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2 — Biphenyl group, 3 — biphenyl group, 4-biphenyl group, p — phenol group, p — terninol group 3 — p, terphenyl 2-noryl, m-terphenyl 4-yl,
- phenyl, 1-naphthyl, 2-naphthyl, 9_phenanthryl, 2—biphenylyl, 3—biphenylyl, and 4—biphenylylole are preferred.
- P-trinole group, 3,4-xylyl group and the like are preferred.
- the aryloxy group having 6 to 40 carbon atoms which may have a substituent of R i ⁇ R 3 is a group represented by 1 O a r, and specific examples of A r are as described above. Examples are the same as those described for the aryl group, and preferred examples are also the same.
- Examples of the aralkyl group having 7 to 40 carbon atoms which may have a substituent of R i R s include, for example, benzyl group, 1-phenylethyl group, 2-phenylethynole group, and 1-phenyl Norei sopro pinole group, 2 — phenyl isopropyl group, phenyl tert-butyl group, ⁇ — naphthylmethyl group, 1 — ⁇ — naphthylethyl group, 2 _ 1-naphthylechinole group,
- benzyl group p-cyanobenzyl group, m-cyanobenzyl group, o_cyanobenzyl group, 1-phenylenoletinol group, 2-phenylenoletinol group, 1-phenylinolepropynole group, 2-phenylphenyl isopropyl group and the like.
- alkenyl group having 2 to 40 carbon atoms which may have a substituent of R i R s include a vinyl group, an aryl group, a 1-butenyl group, a 2-butynole group, and a 3 —Buteninole, 1,3 —butanenyl, 1-methylvinyl, styryl, '2,2—diphen-rubyl, 1,2 —dipheninole vinylinole, 1 —methinorea Linole group, 1,1-dimethylaryl group, 2-methylaryl group, 1-phenylenole group, 2-phenylenyl group, 3-phenylenole group, 3,3-diphenylene Lyl, 1,2—dimethylaryl, 1-phenyl-1—ptenyl, 3—funy1peptenyl, and the like, preferably l-noryl, 2,2 —Diphenylvinyl group, 1, 2 —diphenylvinyl group
- R! R s alkylamino group having 1 to 80 carbon atoms which may have a substituent, arylamino group having 6 to 80 carbon atoms which may have a substituent, substituent Aralkyl amino having 7 to 80 carbon atoms which may have Is a group represented as one NQ i Q s, Q i, is a specific example of Q 2, each independently, said alkyl group, said ⁇ Li Lumpur groups, described in the Araru Kill group The same ones are mentioned, as are the preferred examples.
- Examples of good alkylsilyl groups having 3 to 10 carbon atoms having a substituent of R 1 to R 3 include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, and butyldimethylsilyl group. And a propyldimethylsilyl group.
- Examples of the aryl silyl group having 6 to 30 carbon atoms which may have a substituent of R i to R 3 include triphenylsilyl group, phenyldimethylsilyl group, and t-butyldiphenyl. An enylsilyl group is exemplified.
- the cyclic structure formed when there are a plurality of R i to R 3 includes an unsaturated 6-membered ring such as a benzene ring, and a saturated or unsaturated 5- or 7-membered ring. And the like.
- X is a group represented by any of the following general formulas (4) to (9).
- R 4 to R 13 each independently represent a hydrogen atom, a halogen atom, or an optionally substituted carbon atom having 1 to 40 carbon atoms (preferably having 1 to 40 carbon atoms).
- An alkoxy group having 0 (preferably 1 to 30 carbon atoms), an aryl group having 6 to 40 (preferably 6 to 30 carbon atoms) which may have a substituent, a substituent An aryloxy group having 6 to 40 carbon atoms (preferably 6 to 30 carbon atoms), and 7 to 4.0 carbon atoms (preferably 7 to 40 carbon atoms) 30) an aralkyl group, an optionally substituted alkenyl group having 2 to 40 carbon atoms (preferably 2 to 30 carbon atoms), and an optionally substituted alkenyl group having 1 to 80 carbon atoms.
- R 4 to R 13 may each be plural, and adjacent ones may form a saturated or unsaturated cyclic structure. Specific examples of each group represented by R 4 R 13 include the same as those described for R and R 3 above, and preferred examples are also the same.
- Y i Y a are each independently one CR (R is a hydrogen atom, a group bonded to X in the general formulas (1) and (3) or f R — 4 R ⁇ RR ⁇ R ⁇ R i) or if it is an elementary S atom and a nitrogen atom, the number is at least two in the same ring.
- the group represented by the general formula (4) has any one of the following structures.
- the group represented by the general formula (5) preferably has any one of the following structures.
- the group represented by the general formula (6) includes any of the following structures
- the group represented by the general formula (7) includes any of the following structures
- the group represented by the general formula (8) preferably has any one of the following structures.
- cz represents a group represented by the following general formula (10) or (11).
- A is a single bond, one R 14 R 15 ) n — ( n is an integer of l to 3), one Si R, fi R, 7 — Represents NR 18 —, 10 — or 1 S —, and R 14 and R 15 , R 16 and R 17 may combine with each other to form a saturated or unsaturated cyclic structure .
- R 1 4 ⁇ R 2. Are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 30 carbon atoms which may have a substituent, or a carbon atom having 3 to 20 carbon atoms which may have a substituent.
- Alkenyl group Alkylamino group having 1 to 80 carbon atoms which may have a substituent, arylamino group having 6 to 80 carbon atoms which may have a substituent, having a substituent
- Aralkylamino groups having 7 to 80 carbon atoms alkyl silyl groups having 3 to 10 carbon atoms which may have a substituent, and aryl groups having 6 to 30 carbon atoms which may have a substituent Rusilyl group Is a Shiano group.
- Specific examples of the groups represented by are the same as those described for R 1 to R 3 , and preferred examples are also the same.
- Z is an alkyl group having 1 to 20 carbon atoms which may be substituted, an aryl group having 6 to 18 carbon atoms which may be substituted, or 7 to 4 carbon atoms which may have a substituent Represents an aralkyl group of 0.
- Examples of the alkyl group having 1 to 20 carbon atoms for Z include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isoptyl 'group, and a t-group.
- n one-butyl radical, n - pentyl radical, n - to Kishinore radical, n - to Puchinore group, eta 'Okuchinore group, over Bruno Ninore radical, n one decyl radical, n - Undeshiru radical, n - dodecyl radical, n - Application Benefits Decyl group, n—tetradecyl group, n-pentadecyl group, n—hexadecyl group, n—heptadecyl group, n—octadecyl group, neopentic And a 1-methylpentynole group, a 2-methylpentyl group, a 1-pentynolehexyl group, a 1-butylpentyl group, a 1-heptinoleoctynole group, and a 3-methylpentyl group. And methyl, e
- aryl group for Z examples include a phenyl group, a naphthyl group, a tolyl group, a biphenyl group, a terphenyl group and the like, and preferably a phenyl group, a biphenyl group And a tolyl group.
- Examples of the aralkyl group of Z include a ct-naphthylmethyl group,
- C z is a carbazolyl group which may have a substituent or an arylcarbazolyl group which may have a substituent. Especially preferred.
- Examples of the substituent of each group exemplified in the general formulas (1) to (3) include a nitrogen atom, a hydroxyl group, an amino group, a nitro group, a cyano group, an alkyl group, and an alkenyl group.
- the material for an organic EL device of the present invention is preferably a host material for an organic EL device.
- the organic EL device of the present invention in an organic EL device in which one or more organic thin film layers having at least a light emitting layer are sandwiched between a cathode and an anode, at least one of the organic thin film layers is The material for an organic EL device of the present invention is contained.
- Examples of the structure of the multilayer organic EL device include: anode / hole transport layer (hole injection layer) / light emitting layer / cathode; anode / light emitting layer / electron transport layer (electron injection layer) / cathode , Anode / hole transport layer (hole injection layer) / light-emitting layer / electron transport layer (electron injection layer) / cathode, anode / hole transport layer (hole injection layer) / luminous layer Z hole barrier layer / electron Examples include those stacked in a multilayer structure such as a transport layer (electron injection layer) / a cathode. ''
- the light emitting layer is preferably composed of a host material and a phosphorescent light emitting material, and the host material is preferably composed of the material for an organic EL device.
- phosphorescent quantum yield is high, and the external quantum efficiency of the light-emitting element can be further improved.
- Metal complexes such as platinum complexes and platinum complexes are preferred, iridium complexes and platinum complexes are more preferred, and orthometallated iridium complexes are most preferred.
- orthometalated metal complex the following complex is preferred.
- a reducing dopant is added to an interface region between the cathode and the organic thin film layer.
- Examples of the reducing dopant include an alkali metal, an alkali metal complex, an alkaline metal compound, an alkaline earth metal, an alkaline earth metal complex, an alkaline earth metal compound, and a rare earth metal. And at least one selected from rare earth metal complexes, rare earth metal compounds, and the like.
- the alkali metals include Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV), C s (work function: 1.95 eV), and the work function is 2. Those with 9 eV or less are particularly preferred. Of these, preferably K, Rb, Gs, more preferably Rb or Cs, and most preferably Cs.
- the alkaline earth metals include Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV), and Ba (work function: 2.5 eV). 2 e V), and those having a work function of 2.9 eV or less are particularly preferable.
- rare earth metal examples include Sc, Y, Ce, Tb, and Yb, and those having a work function of 2.9 eV or less are particularly preferable.
- preferred metals have particularly high reducing ability, and the addition of a relatively small amount to the electron injection region can improve the emission luminance and extend the life of the organic EL device.
- B a O, S r O , C a O ⁇ Pico were mixed these (0 ⁇ x ⁇ 1) and, B a x C a! - x O (0 ⁇ x ⁇ 1) , and the like, B a O, S r O , C a O is preferred arbitrariness.
- the alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex each include at least one of an alkali metal ion, an alkaline earth metal ion, and a rare earth metal ion as metal ions. There is no particular limitation as long as it contains one.
- the ligand is quinoline Benzoquinolinolone, ataridinore, phenanthrinorenole, hydroxyf-norexoxazole, hydroxyfenixolenozole, hydroxyzirino roxazinazole, hydroxyzinolinorezinole, hydrazinoxylenozole Ninorepyridin, Hydroxypheninolebenzomi Dazonore, Drooxybenzotriazole, Hydroxyphnorevolan, Bibilygil, Phanant Mouth Lin, Phthalocyanine, Ponolefinelin, Cyclopentagen, ⁇ -Dike Preferred are, but not limited to, tones, azomethines, and derivatives thereof.
- reducing dopant As a form of addition of the reducing dopant, it is preferable to form a layer-like or island-like in the interface region.
- a reducing dopant As a forming method, a reducing dopant is deposited by a resistance heating evaporation method, and at the same time, an organic substance which is a luminescent material and an electron injection material which forms an interface region is simultaneously deposited, and the reduced dopant is dispersed in the organic substance. Is preferred.
- reducing dopant 100: 1 to 1: 100 in a molar ratio, preferably 5 ::! ⁇ 1: 5.
- a light emitting material or an electron injecting material which is an organic layer at the interface is formed in a layer, and then the reducing dopant is independently deposited by a resistance heating evaporation method.
- the layer is formed with a thickness of 0.1 to 15 nm. .
- the reducing dopant is formed in the shape of an island
- the light emitting material or the electron injecting material which is the organic layer at the interface
- the reduced dopant is independently deposited by resistance heating evaporation.
- the island thickness is from 0.05 to: L nm.
- the organic EL device of the present invention has an electron injection layer between the light emitting layer and the cathode, and the electron injection layer contains a nitrogen-containing ring derivative as a main component.
- an aromatic heterocyclic compound containing at least one heteroatom atom in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferable.
- nitrogen-containing ring derivative for example, a derivative represented by the general formula (A) is preferable.
- R 2 to R 7 are each independently a hydrogen atom, a halogen atom, an oxy group, an amino group, or a hydrocarbon group having 1 to 40 carbon atoms, and these may be substituted.
- Examples of the halogen atom include the same as those described above.
- Examples of the amino group which may be substituted include those similar to the aforementioned alkylamino group, arylamino group, and aralkylamino group.
- hydrocarbon group having 1 to 40 carbon atoms examples include a substituted or unsubstituted alkyl group, alkenyl group, cycloalkyl group, alkoxy group, aryl group, heterocyclic group, aralkyl group, aryloxy group, and alkoxy group. And a cicarbonyl group.
- This alkyl group, alkenyl Examples of the alkyl group, the cycloalkyl group, the alkoxy group, the aryl group, the heterocyclic group, the aralkyl group and the aryloxy group include the same as those described above.
- Examples of Y ′ include the same as the above-mentioned alkyl group.
- M is aluminum (A 1) ⁇ dium (G a) or indium (In), and is preferably I 11.
- L in the general formula (A) is a group represented by the following general formula (A ′) or (A ′ ′).
- R 8 to R 12 are each independently a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and adjacent groups form a cyclic structure.
- R 13 to R 27 are each independently a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and a group which is adjacent to each other is preferred. It may form a ring structure.
- the divalent group may be a tetramethylene group, a pentamethylene group, or a hexamethylene group.
- a nitrogen-containing five-membered ring derivative is also preferable, and the nitrogen-containing five-membered ring is preferably an imidazole ring, a triazole ring, or tetrazole. Ring, oxadiazole ring, thiadiazole ring, oxatriazole ring, thiatriazole ring, and the like.
- the nitrogen-containing 5-membered ring derivative include a benzoimidazole ring, a benzotriazole ring, and a pyridinoimidazole ring.
- Pirimi It is a diinomidazole ring or a pyridazinomidazole ring, and particularly preferably a ring represented by the following general formula (B).
- L B represents a divalent or higher linking group, for example, carbon, Keimoto, nitrogen, boron, oxygen, sulfur, metals (e.g., burrs ⁇ beam, Beri Li ⁇ beam), aromatic Examples thereof include a hydrocarbon ring and an aromatic heterocyclic ring. Of these, a carbon atom, a nitrogen atom, a silicon atom, a boron atom, an oxygen atom, a sulfur atom, an aryl group, and an aromatic heterocyclic group are preferable. A carbon atom, a silicon atom, an aryl group and an aromatic heterocyclic group are more preferred.
- the aryl group and the aromatic heterocyclic group of LB may have a substituent, and the substituent is preferably an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or an amino group.
- the substituent is preferably an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or an amino group.
- L B As an example of L B include those shown below:.
- Aliphatic hydrocarbon group RB 2 is a linear, branched or cyclic alkyl group (preferred properly 1-2 0 carbon atoms, yo Ri favored properly having 1 to 1 2 carbon atoms, especially preferred properly is a C1- 8 alkyl groups such as, for example, methyl, ethyl, is 0—propinole, tert-butyl, tinole, n—octinole, n—desinole, n—hexadecinole, cyclopropinole, cyclopentyl, Cyclohexyl, etc.), alkenyl group (preferably having 2 to 20 carbon atoms, more preferably having 2 to 12 carbon atoms, and particularly preferably having 2 to 8 carbon atoms).
- alkenyl group preferably having 2 to 20 carbon atoms, more preferably having 2 to 12 carbon atoms, and particularly preferably having 2 to 8 carbon atoms.
- alkynyl group preferably having 2 to 20 carbon atoms, more preferably having 2 to 1 carbon atoms.
- C2 -C8 Alkylsulfonyl groups der is, for example, propargyl, 3 -. Penchuru etc.) der is, arbitrary preferable that the alkyl group.
- Li Lumpur groups RB 2 is' Ri monocyclic or condensed der, favored properly the carbon number of 6-3 0, yo Ri favored properly having a carbon number of 6 to 2 0, is properly favored by al carbon atoms 6 to 12 aryl groups, for example, phenyl, 2-methylinoline, 3—methylphenoline, 4—methinoleline, 2—methoxynoline, 3 — Tri-funolelo-methinolefeninole, pentafluorophenyl, 1-naphthyl, 2-naphthyl and the like.
- the heterocyclic group of R B2 is a monocyclic or condensed ring, preferably has 1 to 20 carbon atoms, more preferably has 1 to 12 carbon atoms, and further preferably has 2 to 2 carbon atoms. It is a heterocyclic group of 10 and is preferably an aromatic heterocyclic group containing at least one of a nitrogen atom, an oxygen atom, a sulfur atom and a selenium atom.
- heterocyclic group examples include, for example, pyrrolidine, Piperidin, piperazine, morpholine, thiophene, serenophen, furan, pyrrole, imidazonole, pyrazole, pyridine, pyrazine, pyridazine, pyrimidine, triazole, triazine , Indonele, indazole, purine, thiazoline, thiazoline, thiadiazole, thixazoline, oxazole, oxazinezil, quinoline, isoquinolin, phthalazine, naphthyridine, quinoxaline, quinazoline , Cinnoline, pteridine, acridine, phenanthine linole, phenazine, tetrazonole, benzimidazo mono, benzoxazole, benzothiazo mono, benzotriazole, tetra Lazydenden, phorbazo
- Aliphatic hydrocarbon group represented by R B 2 ⁇ Li Lumpur group ⁇ Pi heterocyclic group rather it may also have a substituent, is a substituent group which you express in the L B It is the same as the substituent described above, and the same applies to a preferable substituent.
- RB 2 is preferably an aliphatic hydrocarbon group, an aryl group or a complex ring group, more preferably an aliphatic hydrocarbon group (preferably having 6 to 30 carbon atoms, More preferably a group having 6 to 20 carbon atoms, more preferably a group having 6 to 12 carbon atoms) or an aryl group, and further preferably an aliphatic hydrocarbon group (preferably an aliphatic hydrocarbon group). Or more preferably 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and still more preferably 2 to 10 carbon atoms).
- Z B 2 represents an atom group necessary for forming an aromatic ring.
- the aromatic ring formed by Z B 2 is an aromatic hydrocarbon ring, rather good is neither an aromatic heterocyclic ring, and as a specific example, for example, benzene ring, pyridinium Jin ring, pyrazine ring, pyrimidone Gin Ring, pyridazine ring, triazine ring, pyrrole ring, franne ring, thiophene ring, serenophene ring, teropene phen ring, imidazole ring, thiazole ring, selenazole ring, terrazole ring, thiadiazole Ring, oxazidazole ring, virazole ring, etc., preferably a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, and more
- the aromatic ring formed by Z B 2 is rather good also form a condensed ring with other ring to be al may have a substituent.
- the substituent is the same as the above-mentioned substituent of the group represented by LB, and is preferably an alkyl group, an alkenyl group, an alkyl group, an aryl group or an aryl group.
- an aryl, alkoxy, aryloxy and aromatic heterocyclic group particularly preferably an alkyl group, an aryl group or
- n B 2 is an integer of 1 to 4, and preferably 2 to 3.
- n B 2 is an integer of 1 to 4, and preferably 2 to 3.
- those represented by the following general formula '(B') are more preferable.
- R B 7 1, R B 7 2 and R B 73 are each Ri similar der and RB 2 in the general formula (B), also preferred correct ranges are also the same.
- Z B 7 1, ZB 72 and Z B 7 3 are the same as Z B 2 in the general formula (B), respectively, also preferred correct ranges are also the same.
- L B 7 1, L B 7 2 and L B 7 3 each represent a linking group
- the general formula (B) are exemplified those divalent examples of L B in, is favored properly, single bond, a And a linking group comprising a divalent aromatic hydrocarbon ring group, a divalent aromatic heterocyclic group, and a combination thereof, and more preferably a single bond.
- L B 7 1, L B 7 2 and L B 7 3 may have a substituent, is a substituent represented by L B in the general formula (B)
- the substituents are the same as those described above, and the preferred substituents are also the same.
- Y represents a nitrogen atom, a 1,3,5-benzenetrilyl group or a 2,4,6-triazinetrilyl group.
- the 1,3,5-benzenetrilyl group may have a substituent at the 2,4,6-position.
- substituents include an alkyl group, an aromatic hydrocarbon ring group, Halogen atom and the like.
- 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. If the electron injection layer is composed of an insulator or a semiconductor, current leakage can be effectively prevented, and the electron injection property can be improved.
- Such an insulator is selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, halides of alkaline metal and halides of alkaline earth metal. It is preferred to use at least one metal compound. It is preferable that the electron injection layer is made of such an alkali metal chalcogenide because the electron injection property can be further improved.
- L i 2 ⁇ , L i ⁇ , N a 2 S, N a 2 S e and N a ⁇ is exemplified et al is, preferred correct
- the earth metal chalcogenide include CaO, BaO, SrO, BeO, BaS, and CaSe.
- Preferred alkali metal halides include, for example, LiF, NaF, KF, LiCl, KCl and NaCl.
- alkaline earth metal halides e.g., fluorides and the like C a F 2, B a F 2, S r F 2, M g F 2 and B e F 2, fluoride Halides other than halides.
- Semiconductors include B a, C a, S r, Y b, A l, G a, I 1, L i, N a, C d, M g, S i, T a, S b and An oxide, a nitride, an oxynitride or the like containing at least one element of Zn may be used alone or in combination of two or more. Further, it is preferable that the inorganic compound constituting the electron injection layer is a microcrystalline or amorphous insulating thin film. The electron injection layer is composed of these insulating thin films If so, a more uniform thin film is formed, so that pixel defects such as dark spots can be reduced. Examples of the organic compound include the above-mentioned alkaline metal chalcogenide, alkaline earth metal chalcogenide, halide of alkaline metal and halo of alkaline earth metal. Genides and the like.
- the electron injection layer in the present invention may preferably contain the above-mentioned reducing donor.
- the organic EL device of the present invention preferably has a hole transport layer between the light emitting layer and the anode, and the hole transport layer preferably contains an arylamine derivative as a main component.
- the hole transporting material contained in the hole transporting layer preferably has a triplet energy of 2.5-3.7 eV, more preferably 2.8-3.7 eV. V is even more preferred.
- Ar 7 is an aromatic group having 6 to 40 carbon atoms
- Ar 8 and Ar 9 are each a hydrogen atom or an aromatic group having 6 to 40 carbon atoms.
- m is an integer from 1 to 6.
- a r 1. And A r 1 6 is an aromatic group having 6-4 0 carbon atoms, A r 1 1 ⁇ A r 1 5 is a hydrogen atom or a carbon atoms respectively 6-4 0 is an aromatic group, and the condensed numbers p, q, r, and s are each 0 or 1.) '
- a preferable aryl group having 5 to 40 nuclear atoms is phenylene.
- Examples of the preferred arylene group having 5 to 40 nuclear atoms include phenylene, naphthylene, anthranylene, phenanthylene, pyrenylene, colorylene, biphenylene, and terfene.
- the aromatic group having 6 to 40 carbon atoms may be further substituted by a substituent.
- Preferred examples of the substituent include an alkyl group having 1 to 6 carbon atoms (ethyl group, Methyl group, i-propyl group, n-propynole group, s-butyl group, t-butyl group, pentyl group, hexyl group, cyclopentyl group, cyclohexyl group, etc.), having 1 to 6 carbon atoms Alkoxy groups (ethoxy, methoxy, i-propoxy, n-butoxy, s-butoxy, t-butoxy, pentoxy, hexyloxy, cyclopentoxy, cycloalkyl A hexyloxy group), an aryl group having 5 to 40 nuclear atoms, and an aromatic group having 5 to 40 nuclear atoms.
- alkyl group having 1 to 6 carbon atoms ethyl group, Methyl group, i-propyl group, n-propynole group, s-but
- An amino group substituted with a real group an ester group having an aryl group having 5 to 40 nuclear atoms, an ester group having an alkyl group having 1 to 6 carbon atoms, a cyano group, a nitro group, A halogen atom.
- the anode of the organic EL device plays a role of injecting holes into the hole transport layer or the light emitting layer, and it is effective that the anode has a work function of 4.5 eV or more. It is.
- Specific examples of the anode material used in the present invention include indium tin oxide alloy (ITO), tin oxide
- the cathode a material having a small work function is preferable for the purpose of injecting electrons into the electron injection layer or the light emitting layer.
- the material of the cathode is not particularly limited, but specifically, indium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-metal, aluminum-scandium-lithium alloy, magnesium-silver alloy Etc. can be used.
- the method for forming each layer of the organic EL device of the present invention is not particularly limited. Conventionally known formation methods such as a vacuum deposition method and a spin coating method can be used.
- the organic thin film layer containing the compound represented by any one of the general formulas (1) to (3) used in the organic EL device of the present invention may be formed by vacuum evaporation, molecular beam evaporation (MBE), or a solvent.
- the solution can be formed by a known method such as a coating method such as a diving method, a spin coating method, a casting method, a bar coating method, a roll coating method, or the like.
- each organic layer of the organic EL device of the present invention is not particularly limited. However, in general, if the thickness is too small, defects such as pinholes are likely to occur. Therefore, the range of several nm to 1 ⁇ m is usually preferable.
- the mixture was stirred at 0 ° C for 1 hour. Thereafter, the temperature was raised to room temperature, followed by stirring for 6 hours. Further, 35 milliliters of 5% hydrochloric acid was added to the reaction solution, and the mixture was stirred at room temperature for 40 minutes. After separating the reaction solution into two layers, the organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. 5 minutes of organic solvent
- reaction solution was cooled to 170 ° C, and trisopropyl borate 4.2 milliliters (18 mmo1) was diluted to 6 milliliters of ether.
- the solution was added dropwise over 20 minutes and stirred at 70 ° C. for 1 hour. Thereafter, the temperature was raised to room temperature, followed by stirring for 6 hours. Further, 15 milliliters of 5% hydrochloric acid was added to the reaction solution, and the mixture was stirred at room temperature for 30 minutes.
- the organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. After evaporating the organic solvent under reduced pressure to about 1/5, the precipitated crystals were filtered, washed successively with a mixed solvent of toluene and normal hexane and normal hexane, and
- the mixture was cooled to room temperature, and the precipitated crystals were separated by filtration.
- the obtained crystals were washed with water, methanol and hexane in that order to obtain 3.9 g of crystals.
- the compound was dissolved by heating in toluene and left at room temperature for recrystallization to obtain 2.7 g of a compound (C14) (3.4 mmo1, yield 63%).
- the target compound was identified by 90 MHz NMR and mass spectrometry. The results of FD-MS measurement are shown below.
- the resultant was cooled to room temperature, and the precipitated crystals were separated by filtration.
- the obtained crystals were washed sequentially with water, methanol and hexane to obtain 2.8 g of crystals.
- the compound was dissolved by heating in toluene and left at room temperature for recrystallization to obtain 1.8 g of compound (C22) (2.3 mmol, yield: 48%).
- the target compound was identified by 90 MHz NMR and mass spectrometry. The measurement results of FD-MS are shown below.
- the mixture was cooled to 0 ° C., and diluted hydrochloric acid obtained by diluting 4 milliliters of concentrated hydrochloric acid with 100 milliliters of water was added to make the solution acidic.
- diluted hydrochloric acid obtained by diluting 4 milliliters of concentrated hydrochloric acid with 100 milliliters of water was added to make the solution acidic.
- the organic layer is washed with 70 milliliters of water and saturated saline in this order, and the organic layer is separated again and dried over anhydrous magnesium sulfate. did.
- the solution was filtered, the solution was concentrated under reduced pressure, and the obtained viscous solid was dissolved in TH20 milliliter, hexane 70 milliliter was added, and the precipitated crystal was filtered under reduced pressure.
- the obtained crystals were washed with water, methanol and hexane in that order to obtain 2.5 g of crystals. Further, the compound was dissolved by heating in toluene and left to stand at room temperature for recrystallization to obtain 2.0 g of compound (C66) (1.9 mm 01, yield: 71%).
- the target compound was identified by 90 MHz NMR and mass spectrometry. The measurement results of FD-MS are shown below.
- the resultant was cooled to room temperature, and the precipitated crystals were separated by filtration.
- the obtained crystals were washed with water, methanol and hexane in that order to obtain 1.9 g of crystals.
- the compound was dissolved by heating in toluene and left to stand at room temperature for recrystallization to obtain 1.4 g of a compound (C26) (1.6 mmo1, yield 53%).
- the product was identified as the target by 90 MHz NMR and mass spectrometry. FD-MS measurement results are shown below.
- the obtained crystals were washed with water, methanol and hexane in that order to obtain 2.7 g of crystals. Further, the compound was dissolved by heating in toluene and left to stand at room temperature for recrystallization to obtain '2.1 g of compound (C33) (2.0 mmo1, yield 68%). The product was identified as the target by 90 MHz NMR and mass spectrometry. The results of FD-MS measurement are shown below.
- the mixture was added dropwise over 20 minutes and stirred at 120 ° C for 1 hour. Thereafter, the temperature was raised to room temperature, and the mixture was stirred for 8 hours.
- the reaction solution was further acidified by adding 4% hydrochloric acid, and stirred at room temperature for 40 minutes. After separating the reaction solution into two layers, the organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. After evaporating the organic solvent under reduced pressure to about 1/5, the precipitated crystals were filtered, washed successively with a mixed solvent of toluene-normal hexane and normal hexane, and 2.4 g of the intermediate (IM16) was obtained. (5.5 mm 01, yield 65%). The FD-MS measurement results of the obtained compound are shown below.
- the glass substrate with the ITO transparent electrode having a thickness of 25 mm ⁇ 75 mm ⁇ 0.7 mm was subjected to ultrasonic cleaning for 5 minutes in isopropyl alcohol, followed by UV ozone cleaning for 30 minutes.
- the glass substrate with the transparent electrode after cleaning is mounted on a substrate holder of a vacuum deposition apparatus.
- TPD 2 32 was deposited.
- This TPD232 film functions as a hole injection layer.
- the following TBDB was formed in a thickness of 30 nm on the TPD232 film.
- This TBDB film functions as a hole transport layer.
- the compound (C5) having a thickness of 30 ⁇ m was deposited on the TBDB film as a host material to form a light emitting layer.
- the above (K13) was added as a phosphorescent Ir metal complex dopant.
- the concentration of (K-13) in the light emitting layer was 5% by weight.
- This film functions as a light emitting layer.
- the above (A-7) having a thickness of 1 O nm was formed on this film.
- This (A-7) film functions as a hole barrier layer.
- an aluminum complex of the following 8-hydroxyquinoline (Alq film) having a thickness of 40 nm was formed on this film.
- This A1q film functions as an electron injection layer.
- a halogenated alkali metal was deposited to a thickness of 0.2 nm, and then aluminum was deposited to a thickness of 1501111.
- This 1 / LiF acts as a cathode.
- an organic EL device was manufactured.
- This device was subjected to a current test, the voltage 5. 5 V, at a current density 0. 2 3 mA / cm 2 , green light emission with an emission luminance of 1 0 2 cd / m 2 was obtained, the chromaticity coordinates (0.30, 0.63), and the luminous efficiency was 44.3 cd ZA.
- the device was driven at a constant current at an initial luminance of 500 cd Zm 2 , and the time required for halving the luminance to 250 cd / m 2 was 8 21 hours. Table 1 shows the results.
- An organic EL device was prepared in the same manner as in Example 1, except that the compound shown in Table 1 was used in place of the compound (C5) as the host material of the light emitting layer. Current density, brightness, luminous efficiency, The chromaticity and luminance half-life were measured and are shown in Table 1.
- An organic EL device was prepared in the same manner as in Example 1, except that the following known compound (CBP) was used instead of the compound (C5) as the host material of the light emitting layer.
- CBP the following known compound
- the current density, luminance, luminous efficiency, chromaticity, and luminance half-life were measured and are shown in Table 1.
- An organic EL device was prepared in the same manner as in Example 1 except that the following known compound (CMTTP) was used instead of the compound (C5) as the host material of the light emitting layer.
- Table 1 shows the measured values of voltage, current density, luminance, luminous efficiency, chromaticity, and luminance half-life.
- the organic EL device using the material for an organic EL device of the present invention can emit green light with high efficiency and long life.
- the glass substrate with the ITO transparent electrode having a thickness of 25 mm ⁇ 75 mm ⁇ 0.7 mm was subjected to ultrasonic cleaning for 5 minutes in isopropyl alcohol, followed by UV ozone cleaning for 30 minutes.
- the glass substrate with the transparent electrode after cleaning is mounted on a substrate holder of a vacuum evaporation apparatus.
- TPD 2 32 was deposited. This TPD 2 The 32 film functions as a hole injection layer.
- the following TCTA was formed into a film having a thickness of 10 nm on the TPD232 film.
- This TCTA film functions as a hole transport layer.
- the above compound (C 8) having a thickness of 3 O nm was deposited on the TCTA film to form a light emitting layer.
- the above (K_10) was added as a fluorescent Ir metal complex dopant.
- the concentration of (K-10) in the light emitting layer was 7.5% by weight.
- This film functions as a light emitting layer.
- the above (A-7) having a thickness of 30 nm was formed on this film.
- This Alq film functions as an electron injection layer.
- a halogenated alkali metal LiF was deposited to a thickness of 0.2 nm, and then aluminum was deposited to a thickness of 150 nm.
- This AlZLiF works as a cathode. In this way, an organic EL device was manufactured.
- This device time current test row of ivy and, voltage 6. 8 V, at a current density 0. 3 7 m A / cm 2, a luminance of emitted light 1 0 3 cd / m 2 was obtained, the chromaticity The coordinates were (0.18, 0.38) and the luminous efficiency was 27.8 cd / A.
- the device was driven at a constant current with an initial luminance of 500 cd / m 2 , and the time required for halving the luminance to 250 cd Zm 2 was 235 hours. Table 2 shows the results.
- Example 9 was repeated in the same manner as in Example 9 except that the compounds shown in Table 2 were used instead of the compound (C8) as the host material of the light emitting layer.
- An EL device was fabricated, and the voltage, current density, luminance, luminous efficiency, chromaticity, and luminance half-life were measured in the same manner, and the results are shown in Table 1.
- An organic EL device was prepared in the same manner as in Example 9 except that the above-mentioned compound (CBP) was used in place of the compound (C8) as the host material of the light-emitting layer.
- CBP compound
- the density, luminance, luminous efficiency, chromaticity, and luminance half-life were measured and are shown in Table 2.
- An organic EL device was prepared in the same manner as in Example 9 except that the known compound (CMTTP) was used in place of the compound (C8) as the host material of the light emitting layer.
- Table 2 shows the measured voltage, current density, luminance, luminous efficiency, chromaticity, and luminance half-life.
- An organic EL device was prepared in the same manner as in Example 9 except that a known compound (CTP) shown below was used instead of the compound (C8) as the host material of the light emitting layer.
- CTP a known compound shown below was used instead of the compound (C8) as the host material of the light emitting layer.
- the density, luminance, luminous efficiency, chromaticity, and luminance half-life were measured and are shown in Table 2.
- the organic EL device using the material for an organic EL device of the present invention can emit green light with high efficiency and long life.
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
Description
Claims
Priority Applications (4)
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US10/582,963 US7829204B2 (en) | 2003-12-15 | 2004-12-13 | Material for organic electroluminescent device and organic electroluminescent device using same |
JP2005516257A JP4490923B2 (ja) | 2003-12-15 | 2004-12-13 | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクロルミネッセンス素子 |
EP04807317A EP1696708A4 (en) | 2003-12-15 | 2004-12-13 | MATERIAL FOR ORGANIC ELECTROLUMINESCENCE DEVICE AND ORGANIC ELECTROLUMINESCENCE DEVICE USING THE SAME |
KR1020067011728A KR101158144B1 (ko) | 2003-12-15 | 2004-12-13 | 유기 전기 발광 소자용 재료 및 이를 이용한 유기 전기발광 소자 |
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JP2003-417066 | 2003-12-15 | ||
JP2003417066 | 2003-12-15 |
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US (1) | US7829204B2 (ja) |
EP (1) | EP1696708A4 (ja) |
JP (1) | JP4490923B2 (ja) |
KR (1) | KR101158144B1 (ja) |
CN (1) | CN1895004A (ja) |
TW (1) | TW200524464A (ja) |
WO (1) | WO2005057987A1 (ja) |
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US8735878B2 (en) | 2010-01-15 | 2014-05-27 | Udc Ireland Limited | Charge transporting material and organic electroluminescence device |
KR20130009972A (ko) | 2010-02-26 | 2013-01-24 | 신닛테츠 수미킨 가가쿠 가부시키가이샤 | 유기 전계 발광 소자 |
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US9537111B2 (en) | 2011-05-11 | 2017-01-03 | Idemitsu Kosan Co., Ltd. | Compound, material for organic electroluminescence device, and organic electroluminescence device |
KR20140074936A (ko) | 2011-09-12 | 2014-06-18 | 신닛테츠 수미킨 가가쿠 가부시키가이샤 | 유기 전계 발광 소자 |
WO2013038843A1 (ja) | 2011-09-12 | 2013-03-21 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
US20160149140A1 (en) * | 2013-06-13 | 2016-05-26 | Sk Chemicals Co., Ltd. | Compound for organic electroluminescent device and organic electroluminescent device including the same |
Also Published As
Publication number | Publication date |
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US7829204B2 (en) | 2010-11-09 |
EP1696708A1 (en) | 2006-08-30 |
JPWO2005057987A1 (ja) | 2007-07-19 |
CN1895004A (zh) | 2007-01-10 |
KR101158144B1 (ko) | 2012-06-19 |
JP4490923B2 (ja) | 2010-06-30 |
KR20060121191A (ko) | 2006-11-28 |
US20070104976A1 (en) | 2007-05-10 |
TWI364235B (ja) | 2012-05-11 |
TW200524464A (en) | 2005-07-16 |
EP1696708A4 (en) | 2008-04-23 |
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