WO2008072538A1

WO2008072538A1 - Organic electroluminescent device

Info

Publication number: WO2008072538A1
Application number: PCT/JP2007/073561
Authority: WO
Inventors: Toshihiro Iwakuma; Kazuki Nishimura; Chishio Hosokawa
Original assignee: Idemitsu Kosan Co., Ltd.
Priority date: 2006-12-08
Filing date: 2007-12-06
Publication date: 2008-06-19
Also published as: TW200845452A; JP2008147354A

Abstract

Disclosed is an organic electroluminescent device wherein an organic thin film composed of one or more layers is interposed between a cathode and an anode. In this organic EL device, a light-emitting layer contains a compound having a specific structure as a host material, while containing a metal complex compound having a specific structure including a central metal atom and a corresponding ligand as a dopant. This organic electroluminescent device is free from pixel defects, while having high luminance, high luminous efficiency and long life.

Description

Specification

Organic electoluminescence device

Technical field

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent device, and more particularly, to an organic electroluminescent device having no emission defects and high emission efficiency and a long lifetime. Background art

[0002] Organic electoluminescence (EL) elements utilize the principle that a fluorescent substance emits light by the recombination energy of holes injected from the anode and electrons injected from the cathode by applying an electric field. Self-luminous element.

As light emitting materials for organic EL devices, light emitting materials such as chelate complexes such as tris (8-quinolinolato) aluminum complex, coumarin derivatives, tetraphenylbutadiene derivatives, distyrylarylene derivatives, oxadiazole derivatives and the like are known. Have been reported that light emission in the visible region from blue to red is obtained, and realization of a color display element is expected (see, for example, Patent Documents 1 to 3).

In recent years, it has also been proposed to use an organic phosphorescent material in addition to the light-emitting material for the light-emitting layer of the organic EL element (see, for example, non-patent documents;! To 2).

In this way, high emission efficiency is achieved by utilizing the excited singlet state and triplet state of the organic phosphorescent material in the light emitting layer of the organic EL element. When electrons and holes recombine in an organic EL element, it is thought that singlet excitons and triplet excitons are generated at a ratio of 1: 3 due to the difference in spin multiplicity. If phosphorescent luminescent materials are used, it is conceivable that light emission efficiency of 3 to 4 times that of devices using only fluorescence will be achieved.

In such an organic EL element, an anode, a hole transport layer, an organic light emitting layer, an electron transport layer (a hole blocking layer), in order so that a triplet excited state or a triplet exciton is not quenched. A structure in which layers are stacked such as an electron injection layer and a cathode has been used, and a host compound and a phosphorescent compound have been used for an organic light emitting layer (see, for example, Patent Documents 4 to 5). In these patent documents, 4, 4-N, N dicarbazole biphenyl has been used as a host compound, but this compound has a glass transition temperature of 110 ° C or lower and is too symmetric. For this reason, there is a problem that a short circuit or a pixel defect occurs when the element is subjected to a heat resistance test immediately after crystallization. Further, as phosphorescent complexes, azol complexes are disclosed in Patent Documents 6 to 14;

It was also found that during the deposition, crystal growth occurred in places where foreign matter or electrode protrusions existed, and defects were generated from the initial state before the heat resistance test. In addition, force rubazole derivatives that maintain three-fold symmetry are also used as hosts. However, due to the good symmetry, crystal growth occurs at the locations where foreign matter and electrode protrusions exist when vapor deposition is performed, and it is possible to avoid defects from the initial state before the heat resistance test! .

Patent Document 1: JP-A-8-239655

Patent Document 2: JP-A-7-138561

Patent Document 3: JP-A-3-200889

Patent Document 4: U.S. Pat.No. 6,097,147

Patent Document 5: International Publication WO01 / 41512

Patent Document 6: International Publication WO2004 / 085450

Patent Document 7: WO2005 / 007767

Patent Document 8: JP 2005-53912 A

Patent Document 9: JP-A-2005-68110

Patent Document 10: International Publication WO2006 / 009024

Patent Document 11: JP-A-2006-120762

Patent Document 12: JP-A-2006-120905

Patent Document 13: International Publication WO2006 / 013738

Patent Document 14: International Publication WO2006 / 008976

Non-patent literature: L.F.O'Brien and M.A.Baldo et al improved energy transfenn electro phosphorescent devices "Applied Physics letters Vol. 74 No.3, pp442 ~ 444, January 18, 1999

Non-Patent Document 2: MABaldo et al Very high—efficiencygreen organic lignt-emitting dev ices based on electrophosphorescence ”Applied Physics letters Vol.75 No. l, pp4 ~ 6, July 5, 1999 Disclosure of the invention

Problems to be solved by the invention

[0004] The present invention has been made to solve the above-described problems, and an object thereof is to provide an organic electoluminescence device having a long lifetime and a high luminance and luminous efficiency free from pixel defects. To do.

Means for solving the problem

[0005] As a result of intensive studies to achieve the above object, the present inventors have used a specific host material and a dopant shown below in combination in the light emitting layer of the organic EL element. The present inventors have found that the above problems can be solved and have completed the present invention.

[0006] That is, the present invention relates to an organic EL device in which a single organic layer or a plurality of organic thin film layers are sandwiched between a cathode and an anode, and the light emitting layer hosts a compound represented by the following general formula (1). The present invention provides an organic EL device containing, as a material, a metal complex compound represented by the following general formula ω as a dopant.

[0007] [Chemical 1]

[[00000088]] ((In the formula, CCzz is a carcarrubabazozolyryl group, a carbon number of 1188 to 6600 allylic lucacarrubabazosol ruyl group) , Azaazacarlubabasazolyryl group, an arylene group having a carbon number of 1188 to 6600, and an atalyridininyl group. Fuenoenoxoxasadininyl group or didibebenzozezepipininyl group, which may be substituted !! //! ! //, AArr ^{11 and} AArr ^{22 are} independent carbon numbers, respectively, with or without substitution. 66 to 6600 arylene groups or substitutional or non-substituted carbon number of carbon atoms of 33 to 6600 AArr ^{33 is a} fragrant aromatic carbon-carbonized hydrocarbon group having 66 to 6600 carbon atoms or a substituted group. It is a non-substituted non-substituted polyheterocyclic ring group having a carbon number of 33 to 6600. AArr ⁴⁴ is also capable of substitution. Is a non-substituted non-substituted bevenzensen residue group, or a non-substituted non-substituted thiophene residue residue group. Or a non-substituted non-substituted tritazolazole residue, or a non-substituted non-substituted furfurooleenne residue group or May also be replaced

aa is an integer number of 00 to ~ ;; !!, bb is an integer number of 00 to ~ 44, cc is an integer number of ;; !! ~~ 33 When there are multiple CCzz and AArr ⁴⁴ May be the same as or different from each other.

However, & = 0. When = 1, Ar ³ and Ar ⁴ are benzene residues, and Ar ^{2 is a} phenylcarbazolyl group or carbazolyl group. When _a = l, b = 0 and c = 1, Ar ³ is a benzene residue, and Ar ¹ and Ar ² are phenylcarbazolyl groups. Furthermore, when b = 0 and c = 1, Ar ³ is a benzene residue, and Ar ¹ , Ar ² and Cz are each a carbazolyl group or a phenylcarbazolyl group. )

[0009] [Chemical 2]

(In the general formulas (a) and (b), R to R each independently represent a hydrogen atom, a cyano group,

1 7

Toro group, halogen atom, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted amino group, substituted or unsubstituted alkoxyl group having 1 to 20 carbon atoms, substituted or unsubstituted ! ~ 20 alkylsilyl group, substituted or unsubstituted carbon number;! ~ 20 acyl group, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or substituted or unsubstituted Represents an aromatic heterocyclic group having 3 to 30 carbon atoms. Also, next to R ~ R

1 7 Those in contact with each other are bonded to each other to form a ring structure! /.

M is a metal atom of iridium (Ir), rhodium (Rh), platinum (Pt) or palladium (Pd).

n is an integer from!

However, when M is Ir, n = 3. )

The invention's effect

[0011] The organic EL device of the present invention has a long lifetime with high luminance and luminous efficiency without pixel defects. BEST MODE FOR CARRYING OUT THE INVENTION

The present invention is an organic EL device in which an organic thin film layer comprising at least one light emitting layer or a plurality of layers is sandwiched between a cathode and an anode.

The host material used for the light emitting layer of the organic EL device of the present invention comprises a compound represented by the following general formula (1).

[Chemical 3]

In the general formula (1), Cz represents a carbazolyl group, an 18 to 60 carbon carbazolinolinore group, an azacarbazolyl group, an allylazacarbazolyl group having 18 to 60 carbon atoms, an atalidinyl group, a phenoxazinyl group, or a dibenzo group. It is a zepinyl group and may be substituted.

Examples of the aryl moiety in the allylcarbazolyl group and the allylazacarbazolyl group include, for example, a phenyl group, a 1 naphthyl group, a 2-naphthyl group, a 1 anthrinol group, a 2 ntrinol group, a 9 ntrinol group, 1- F: Nantolinol group, 2 F: Nantolinol group, 3 Phenanthrinol group, 4 Phenanthrinol group, 9 Phenanthrinol group, 1-Naphthenyl group, 2 Naphthacenyl group, 9 Naphthenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2 Biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenylolate 4-inole group, p-terfenolate 3-inole group, p-terfeninole 2-inole group, m-terphenylolate 4-inole group, m-terphenylolate 3-inolele group, m—ter phenolic 1—inole group, o tri Rhe group, m-trinole group, p-trinole group, p-t-butynolephenyl group, P- (2 phenylpropyl) phenyl group, 3 methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1 anthryl group, 4 Examples include a '-methylbiphenyl group, a 4 "-tert-butyl-p-terfenyl group, and a phenyl group, a biphenyl group, a trinole group, an isopropylphenyl group, and a t-butylphenyl group.

In General Formula (1), Ar ¹ and Ar ² are each independently substituted or unsubstituted carbon. A prime group having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon group having 6 to 20 carbon atoms, or a substituted or unsubstituted carbon group having 3 to 20 carbon atoms. A heterocyclic group, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidinyl group, and a triazinyl group are more preferable.

Examples of the aryl group include a phenyl group, a 1 naphthyl group, a 2-naphthyl group, a 1 entrinol group, a 2 entrinol group, a 9 entrinol group, a 1 phenanthrinol group, a 2 phenanthrinol group, a 3 phenanthrinol group, a 4 phenanthrinol group, and 9 Phenanthrinol group, 1-naphthacenyl group, 2 naphthacenyl group, 9 naphthacenyl group, 1-pyrenyl group, 2 pyrenyl group, 4-pyrenyl group, 2 biphenylyl group, 3 biphenylyl group, 4-biphenylinole group, p Terfeninore 4-inore group, p terfeninore 3-inole group, p terfeninole 2-inole group, m terfeninore 4-inole group, m terfeninole 3-inole group, m-terpheninole 2-inore group, o-trinore group, p-trinore group Group, p—t butylphenyl group, p— (2 phenyl Propyl) phenyl group, 3 methyl-2-naphthyl group, 4-methyl-1 naphthyl group, 4-methyl-1 anthryl group, 4'-methylbiphenyl group, 4 "t-butyl-p tert-phenyl group, etc. A naphthyl group, a pyrenyl group, a biphenyl group, a terphenyl group, a tolyl group, an isopropylphenyl group, and the like are preferable.

Examples of the heterocyclic group include 1 pyrrolyl group, 2 pyrrolyl group, 3 pyrrolyl group, pyradyl group, 2-pyridinyl group, 3-pyridinyl group, 4 pyridinyl group, 1 indolyl group, 2 indolinole group, and 3 indolinole group. , 4 Indolinol group, 5 Indolinol group, 6 Indolinol group, 7 Indolinol group, 1 Isoindolyl group, 2 Isoindolyl group, 3-Isoindolyl group, 4 Isoindolyl group, 5-Isoindolyl group, 6-Isoindolyl group, 7-Isoindryl group , 2 frinole group, 3 frinole group, 2 benzofuranyl group, 3 benzofuranyl group, 4 benzofuraninole group, 5-benzofuraninole group, 6-benzofuraninole group, 7-benzofuraninole group, 1 isobenzofuranyl group, 3—Isobenzofuranyl group, 4 Isobenzofuranyl group, 5 Isobenzofuranyl group, 6 Isobenzofuranyl group, 7 Isobenzofuranyl group, 2-quinolinole group, 3-quinolinole group, 4-quinolinole group, 5-quinolinole group, 6-quinolinole group, 7-quinolinol group, 8-quinolinole group, 1 isoquinolinole group, 3-isoquinolyl group, 4-isoquinolinol group, 5- Isoquinolyl group, 6 Isoquinolyl group, 7 Isoquinolyl group, 8 Isoquinolyl group, 2 Quinoxalinyl group, 5 Quinoxalinyl group, 6 Quinoxalinyl group, 1 One strength rubazolyl group, 2 Strength Noreno zolinole group, 3 Strength rubazolyl group, 4 One strength rubazolyl Group, 9 rubazolyl group, 1-phenanthridinyl group, 2 phenanthridinyl group, 3 phenanthridinyl group, 4 phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group, 8 —Phenanthrinidinyl group, 9 Phenanthridinyl group, 10 Phenanthridinyl group, 1 Ataridinyl group, 2 Ataridininole group, 3 Ataridininole group, 4 Ataridininole group, 9 Ataridininole group, 1, 7 Phenothroline-2 Inole group 1, 7 phenanthroline 3-ynole group, 1, 7 phenanthroline 4-yl group, 1, 7 phen Nansuloline 5-yl group, 1, 7 phenoline 6-inole group, 1, 7 phenanthroline 8-inole group, 1, 7 phenanthroline 9 — inole group, 1, 7 phenanthroline 1- 10 inole group, 1,8-Phenanthhroline 2-inole group, 1,8-Phenanthhroline-3-inole group, 1,8-Phenanthuroline-4-inole group, 1,8 Phenanthroline-5-inole group, 1,8 —Phenanthuroline—6-Inole group, 1,8—Phenanthhroline 7—yl group, 1,8—Phenanthhroline 9—yl group, 1,8—Phenanthroline —10—Inole group, 1,9 Phenanthroline 1-Inole group, 1, 9 phenanthroline 1- 3-inole group, 1, 9-phenanthroline 1- 4-inole group, 1, 9-phenanthroline 1-5-inole group, 1, 9 phenanthroline-6-inole group, 1, 9 phenanthroline 7— Nore group, 1,9-phenanthroline 1-8-yl group, 1,9 phenanthroline 1-10 yl group, 1,10 phenanthroline 1-inole group, 1,10 phenanthroline 1-inole group, 1,10 phenanthroline 4-yl group, 1, 10 phenanthroline 5-yl group, 2, 9 phenanthroline 1--yl group, 2, 9 phenanthroline 3-yl group, 2, 9 phenanthroline 4-yl group, 2, 9 Phenylanthroline 5—inore group, 2, 9 Phenylanthroline 6—inore group, 2, 9—Phenanthroline 7 inole group, 2, 9 Phenothroline 8 inole group, 2, 9 Phenothroline 1 10 yl group, 2, 8 Phenothroline 1— Group, 2, 8 phenanthroline — 3 group, 2, 8 phenanthroline 1 4 yl group, 2, 8 phenanthroline 1 -5 group, 2, 8 phenanthroline 1 -6 group, 2, 8 phenanthroline 1 7 Group, 2, 8 phenanthroline 9-yl group, 2, 8 phenanthroline 10-yl group, 2, 7 phenanthroline 1-yl group, 2, 7 phenanthroline 3-yl group, 2, 7 Phenanthro Phosphoric 4-yl group, 2, 7-phenanthroline 5-yl group, 2, 7-phenanthrolin 6-yl group, 2, 7-phenanthroline 8-yl group, 2, 7-phenanthroline 9-yl group, 2, 7 phenanthroline 10-yl group, 1 phenazinyl group, 2 phenazinyl group, 1-phenothiazinyl group, 2 phenothiazinyl group, 3 phenothiazinyl group, 4-phenothiazinyl group, 10-phenothiazinyl group, 1 phenoxazinyl group, 2-phenoxazinyl group, 3 phenoxazinyl group, 4 phenoxazinyl group, 10 phenoxazinyl group, 2 oxazolyl group, 4-oxazolyl group, 5 oxazolyl group, 2 oxadiazolyl group, 5 oxadiazolyl group, 3 flazanyl group, 2 enyl group 2 methyl pyrrole 1-yl group, 2 methyl pyrrole 3-yl group, 2 methyl pyrrole 1 Nore group, 2-methyl pyrrole 5-yl group, 3-methyl pyrrole 1-yl group, 3-methyl pyrrole 2-yl group, 3-methyl pyrrole 4-yl group, 3-methyl pyrrole Nore 5-inole group, 2-t-butyl pyrrole one 4-yl group, 3- (2-phenylpropynole) pyrrole 1-yl group, 2-methyl-1 indolyl group, 4-methyl-1 indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t Butyl 1 Indolyl group, 4 t Butyl 1 indolyl group, 2-t Butyl 3 indolyl group, 4 t Butyl 3 indolyl group, Arylcarbazolyl group, Azacarbazolyl group, Arylazacarbazolyl group, Phenoxazinyl group, Dibenzozepinyl group Carbazolyl group, allylcarbazolyl group, azacarbazolyl group, allylazaca Ba Zoruiru group, Atarijiniru group, Fuenokisajiniru group, dibenzo § benzindolyl group, Benzoi imidazole group, a benzothiazole group, Renzo N § Lil imidazole group and the like

Yes

In the general formula (1), Ar ³ is an aromatic hydrocarbon group having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 60 carbon atoms, and a substituted or unsubstituted carbon group having 6 to 20 carbon atoms. More preferred are benzene, biphenyl, naphthalene, phenanthrene, pyridine, pyrimidine, and triazine residues, and benzene residues, which are preferably aromatic hydrocarbon groups or substituted or unsubstituted heterocyclic groups having 3 to 20 carbon atoms. The group is most preferred.

Specific examples of the aromatic hydrocarbon group include those obtained by removing hydrogen from the specific examples of the Ar ¹ and Ar ² aryl groups, and preferred examples are also the same. Examples of the heterocyclic group include those obtained by removing hydrogen from the specific examples of the heterocyclic group of Ar ¹ and Ar ² and excluding hydrogen, and preferred examples are also the same.

In the general formula (1), Ar ⁴ represents a substituted or unsubstituted benzene residue, a substituted or unsubstituted thiophene residue, a substituted or unsubstituted triazole residue, a substituted or unsubstituted fluorene residue, or a substituted or unsubstituted group. Substituted spirobifluorene residue. In addition, when a phenolene residue, a thiophene residue, or a spirobifluorene residue has a plurality of substituents, the substituents are bonded to each other to form a ring structure! /, May! / .

In addition, examples of — (Ar ⁴ ) b— include the following structures.

[0015] [Chemical 4]

Or

(In the formula, A and Ar ⁶ are each independently the same as Ar ⁴ , and d is an integer of 0 to 3.

When there are a plurality of Ar ^{5 s} , they may be the same or different. )

In general formula (1), a is an integer of 0 to;!, B is an integer of 0 to 4, c is an integer of !! to 3, and when Cz and Ar ⁴ are plural, they are the same or different from each other /!

However, in the general formula (1), when a = 0 and c = 1, Ar ³ and Ar ⁴ are benzene residues, and Ar ² is a phenylcarbazolyl group or carbazolyl group. And a = l, = 0. When = 1, Ar ³ is a benzene residue, and Ar ¹ and Ar ² are phenylcarbazolyl groups. Further, when b = 0 and c = 1, Ar ^{3 is a} benzene residue, and Ar ¹ , Ar ^2, and Cz are carbazolyl groups or phenylcarbazolinole groups.

[0017] In the general formula (1), Α ~Α Γ _⁴ are preferably each an aromatic hydrocarbon group.

In the general formula (1), & = = 1. = 2 where 8 and 8 are phenyl Preferably, the group Ar ³ is a phenyl tolyl group and Ar ⁴ is a phenylene group.

Furthermore, in the general formula (1), a = 0 is preferable, a = 0 force, b = 0, or a = 0 and b = 0, and c = 2 to 3 is preferably an integer. .

The substituents for Cz and Α to Α are each independently a halogen atom, a hydroxyl group, an amino group, a nitro group, a cyano group, an alkyl group, an alkenyl group, a cycloalkyl group, an alkoxy group, or an aromatic hydrocarbon group. An aromatic heterocyclic group, an aralkyl group, an aryloxy group, an alkoxycarbonyl group, a fluorinated alkyl group, a fluorinated aryl group or a carboxyl group.

Examples of the halogen atom include fluorine, chlorine, bromine and iodine.

The amino group is represented as NX ² and X ¹ and X ² are each independently, for example, a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, t butyl group, n pentyl group, n hexyl group, n heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1, 2 —Dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3 dihydroxy-tbutyl group, 1,2,3 trihydroxypropyl group, chloromethyl group, 1 chloroethyl group, 2 chloroethyl group 2-chloro-isobutyl, 1,2-dichloro-ethyl, 1,3-dichloro-isopropyl, 2,3-dichloro-t-butyl, 1,2,3 tri-chloro-propyl, bromomethyl, 1 bromoethyl Group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromot-butyl group, 1,2,3-tribromopropyl group, Iodomethyl, 1-odoethyl, 2-iodoethyl, 2-iodoisobutyl, 1,2-jode yutinole, 1,3 jodoisopropinore, 2, 3 jordio toff "chinole, 1, 2, 3 to Rhodopropinole group, aminomethyl group, 1 aminoethinole group, 2-aminoethinole group, 2-minoisof, chinole group, 1,2-diminoethinole group, 1,3-diminoisopropinole group, 2,3-diamino 1 t-butyl group, 1, 2, 3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicanoethyl group, 1,3 Bruno isopropyl, 2, 3 Jishiano t-butyl group, 1, 2, 3 tricyanopropene pro Pinore group, nitromethyl group, 1 twelve Toroechiru group, 2-two Toroechiru group, 2- two Toroisobuchi Nore group, 1,2-dinitroethinole group, 1,3-dinitroisopropinole group, 2,3-dinitro t-futinore group, 1,2,3 卜 lini port propinole group, Hueninore group, 1 naphthinore group, 2 Naphthino group, 1-linole group, 2- linole group, 9-lin linole group, 1-ph: nan linole group, 2-phenanthrinol group, 3 phenanthrinol group, 4 phenanthrinol group, 9 phenanthrinol group, 1 naphthacenyl Group, 2 naphthacenyl group, 9 naphthacenyl group, 4 styrylphenyl group, 1-pyrenyl group, 2 pyrenyl group, 4-pyrenyl group, 2 biphenylylyl group, 3 biphenylenoreinore group, 4-biphenylenoreinore group, p Terfeninore 4-inore group, p terfeninore 3 inore group, p terfeninore 2 inore group, m terfeninore 4-inore group, m terfeninore 3 Nore group, m-terfeninore 2-inore group, o-trinole group, m-tolyl group, p-trinole group, p-t-butylphenyl group, p- (2-phenylpropynole) phenyl group, 3 methyl-2-naphthyl group, 4 -Methyl-1 naphthyl group, 4-methyl-1 anthrinole group, 4, 1-methylbiphenylyl group, 4 "— t butynole p terfeninore 4-yl group, 2 pyrrolyl group, 3 pyrrolyl group, pyrajuryl group, 2 pyridinyl group Group, 3 pyridinyl group, ₄ pyridinyl group, ₂ indolinole group, ₃ indolinole group, 4 indolyl group, 5-indolyl group, 6 indolinole group, 7 indolinole group, 1 isoindolyl group, 3—isoindoleyl group, 4 isoindolyl group , 5-isoindolyl group, 6-isoindolyl group, 7-isoindolinole group, 2 frinole group, 3 frinole group, 2 benzo'furani Group, 3 benzo'furanino group, 4 benzofuranino group, 5-benzofuranino group, 6-benzofuranole group, 7-benzofuranyl group, 1 isobenzofuranyl group, 3-isobenzofuranyl group, 4 Isobenzofuranyl group, 5-Isobenzofuranyl group, 6-Isobenzofuranyl group, 7-Isobenzofuranyl group, 2 quinolinole group, 3 quinolinole group, 4-quinolinole group, 5 quinolinole group, 6 quinolinole group, 7 quinolyl group , 8-quinolinole group, 1 isoquinolinole group, 3-isoquinolyl group, 4 isoquinolinole group, 5 isoquinolinole group, 6 isoquinolinole group, 7 isoquinolinole group, 8 isoquinolinole group, 2 quinoxalinyl group, 5 quinoxalinyl group, 6 quinoxalinyl group, 6 quinoxalinyl group Force rubazolyl group, 2 force rubazolyl group, 3—force rubazolyl group, 4 force rubazolyl group, 1 force Nansurijiniru 2-Nore group, 3-Atharidinole group, 4-Atharidinole group, 9-Ataridinole group, 1,7-Phenanthrolin 2-yl group, 1,7 Phenanthrolin 3-3-yl group, 1,7 Phenanthroline 4-inole group, 1,7 phenanthroline-5-inol group, 1,7 phenanthroline-6-yl group, 1,7 phenanthroline-1-8-yl group, 1,7 phenanthroline-9-yl group, 1,7 phenanthroline-10-inol group 1,8-phenanthroline 2-inole group, 1,8-phenanthrolin 3-yl group, 1,8-phenanthroline 4-yl group, 1,8-phenanthroline 5-yl group, 1, 8—Phenanthuroline 6-yl group, 1, 8—Phenanthhroline 1—7-Inole group, 1,8 Phenanthroline 1—9-Inole group, 1, 8 Phenanthroline 1—10-Inole group, 1, 9 Phenanthroline 2-—Inole 1, 9 fenance Lorin-3—inore group, 1,9 phenanthroline-4-inole group, 1,9 phenanthroline-5-inole group, 1,9 phenanthroline 6-yl group, 1,9 phenanthroline 1-7-yl group 1, 9 phenanthroline —8—inole group, 1,9 phenanthroline 1 10 inole group, 1,10 phenanthroline 1—2—inole group, 1, 10-phenanthroline 1—3 group, 1, 10—phenanthroline 1— Inole group, 1, 10 phenanthroline 5-yl group, 2, 9 phenanthroline 1-yl group, 2, 9 phenanthroline 3-inole group, 2, 9 phenanthroline 4-inole group, 2, 9 phenanthroline 1-yl group Group, 2, 9 phenanthroline 1-6 yl group, 2, 9 phenanthroline 1 -7 yl group, 2, 9 phenanthroline 1 -8 yl group, 2, 9 phenanthroline 1 -10 yl group, 2, 8 phenanthroline 1 1 —Yil group, 2,8 phenanthroline 3-yl group, 2,8 phenanthroline 4-inole group, 2,8 phenanthroline 5-inole group, 2,8-phenanthroline 6-inole group, 2,8 phenanthroline 7-inole group, 2,8 phenanthroline 9 Group, 2, 8 phenanthroline 10-yl group, 2, 7 phenanthroline — 1-yl group, 2, 7 phenanthroline 3-yl group, 2, 7 phenanthroline 4-yl group, 2, 7 phenanthroline 1 5-yl group, 2, 7 phenanthroline 6-yl group, 2, 7 phenanthroline-8-inore group, 2,7 phenanthroline-9-inore group, 2,7 phenanthroline 10-yl group, 1 phenazinyl Group, 2-phenazinyl group, 1-phenothiazinyl group, 2 phenothiazinyl group, 3 phenothiazinyl group, 4 phenothiazinyl group, 1 phenoxazinyl group, 2 phenoxazinyl group, 3 Enokisajiniru group, 4 Hue Nokisajiniru group, 2 Okisazoriru group, 4 Okisazoriru group, 5 Okisazoriru group, 2- Oxadiazolyl group, 5 Oxadiazolyl group, 3 Frazanyl group, 2 Chenyl group, 3 Chenyl group, 2 Methyl pyrrole 1 yl group, 2 Methyl pyrrole 1 yl 3 yl group, 2 Methyl pyrrole 1 ue 4 yl group, 2 Methyl pyrrole 1 5 Group, 3 methyl pyrrole 1-l-inole group, 3 methyl pyrrole 1- 2 yl group, 3 methyl pyrrole 1- 4 yl group, 3 methyl pyrrole 1- 5 yl group, 2-t-butyl pyrrole 1- 4-yl group, 3-( 2-phenylpropynole) pyrrole 1-yl group, 2-methyl-1 indolyl group, 4-methyl-1 indolyl group, 2 methyl-3 indolyl group, 4-methyl-3 indolyl group, 2-tert-butyl 1 indolinole group, 4 t-butyl 1 Indolyl group, 2-t-butyl 3 indolyl group t-butyl 3-indolyl group and the like can be mentioned.

Examples of the alkyl group include methyl group, ethyl group, 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, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3 dihydroxyisopropyl group, 2,3 dihydroxy-tbutyl Group, 1, 2, 3 trihydroxypropyl group, chloromethyl group, 1-cyclodiethyl group, 2-cyclodiethyl group, 2-cyclodiethyl isobutyl group, 1,2-dicyclodiethyl group, 1,3-dicyclodiethyl isopropyl group 2,3 dichloro-t-butyl group, 1,2,3 trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2- Bromoethyl group, 1,3-Dibromoisopropinole group, 2,3-Dibu-Mouto Motobutinole group, 1,2,3-Tribromopropinore group, Eodomethinole group, 1-Edoethinore group, 2-Edoethinore group, 2-Edoisof, , Tinole group, 1,2—Jodoethinole group, 1,3—Jodoisopropinole group, 2,3-Jododotyl butyl group, 1,2,3-Triodopropyl group, Aminomethyl group, 1 Aminoethyl Group, 2-mininotinole group, 2-mininoisof, tinole group, 1,2-diminoethinole group, 1,3-diminoisopropinole group, 2,3 diminotof, tinole group, 1,2, 3 Triminopropinole group, Cyanomethinole group, 1-Cyanoethyl group, 2-Cyanoethyl group, 2-Cyanoisobutyl group, 1,2-Dicanoethynole group, 1,3-Dicanoisopropinole group, 2,3-disi Annot tert-Butinore group, 1, 2, 3— 卜 Licyanopropinole group, 2 卜 Lomethinole group, 1 1 卜 2 Loetinore group, 2—2 卜 Loetyl group, 2—2 Troisobutyl group, 1, 2— Dinitroethyl group, 1,3-dinitroisopropyl Group, 2,3 dinitro-t-butyl group, 1,2,3 trinitropropyl group, etc.

Yes

[0020] Examples of the alkenyl group include a vinylol group, a linole group, a 1-butur group, a 2-butur group, a 3- group, a teninole group, a 1, 3-group, a tangeninore group, a 1-methino levinore group, a styrinole group, 2,2-diphenylvinyl group, 1,2-diphenylvinyl group, 1-methylallyl group, 1,1-dimethinoreazinole group, 2-methinorea !; no group, 1 phenylenorea !; no group, 2 phenyleno !! Group, 3 phenylaryl group, 3,3 diphenylaryl group, 1,2 dimethylaryl group, 1 phenyl 1-butur group, 3-phenyl 1-butur group and the like.

[0021] Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a 4-methylcyclohexyl group.

The alkoxy group is a group represented by OY, and Y includes, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a tert-butylene group, an n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2 dihydroxyethynole group, 1, 3 Dihydroxyisopropinole group, 2, 3 dihydroxy t-butyl group, 1, 2, 3 trihydroxypropyl group, chloromethyl group, 1 chloroethyl group, 2 chloroethyl group, 2 chloroethyl isobutyl group, 1, 2 dichroic group Ethyl group, 1,3-dichloro isopropyl group, 2,3 dichloro-t butyl group, 1,2,3 trichloro propylene group, bromomethyl group, 1 bromoethyl group, 2-bromo group Tyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromot-butyl group, 1,2,3-tribromopropyl group, odomethyl group, 1-odoethyl group , 2-odoethyl group, 2-odoisobutyl group, 1, 2-jordoethyl group, 1, 3-iodoisopropinole group, 2, 3 jordo toff, chinole group, 1, 2, 3 triode Propinole group, aminomethyl group, 1 aminoethynole group, 2-aminoethinole group, 2-aminoaminobutyl group, 1,2 diaminoethyl group, 1,3 diaminoisopropyl group, 2,3 diamino-tbutyl group, 1, 2,3-triaminopropyl group, cyanomethylol group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicianoethyl group, 1,3-discyanoisopropyl group, 2 , 3 Dicyano t-butyl group, 1, 2, 3 tricyanopropyl group, nitromethyl group 1, 1 2 troethyl group, 2-2 troethyl group, 2-2 troisobutyl group, 1, 2-dinitroethyl group, 1, 3 dinitroisopropyl group, 2, 3 dinitro tert butyl group, 1, 2, 3 trinitro A propyl group etc. are mentioned.

As the aromatic hydrocarbon group, for example, a phenyl group, a 1 naphthyl group, a 2-naphthyl group, a 17 ”entrinole group, a 2-7” entolinole group, a 9 7 ”entolinole group, a 1 phenanthrinol group, 2— Phenanthrinol group, 3-phenanthrinol group, 4 phenanthrinol group, 9 phenanthrinol group, 1-naphthacenyl group, 2 naphthacenyl group, 9 naphthacenyl group, 1-pyrenyl group, 2 pyreninol group, 4 pyrenyl group, 2 biphenylyl group, 3-biphenylyl group, 4-biphenylenoleole group, p terfeninore 4-inore group, p terfeninore 3-inole group, p terfenenore 2-inole group, m-terfeninore 4-inore group, m-terfeninore 3-inore group —Inole group, o Trinole group, m-Trinole group, p Trinole group, p—t Butylhue P- (2 phenylpropyl) phenyl group, 3 methyl-2 naphthyl group, 4-methyl-1 naphthyl group, 4-methinoleyl 1 antolinole group, 4'-methylbiphenylinole group, 4 "—t-butyl-p-terfenyl And the like.

[0023] The aromatic heterocyclic group includes, for example, 1 pyrrolyl group, 2-pyrrolyl group, 3 pyrrolyl group, pyradyl group, 2 pyridinyl group, 3 pyridinyl group, 4 pyridinyl group, 1 indolyl group, 2 indolinole group, 3 Indolinol group, 4 Indolinole group, 5 Indolinole group, 6 Indolinol group, 7 Indolinole group, 1 Isoindolyl group, 2 Isoindolyl group, 3 Isoindolyl group, 4 Isoindolyl group, 5—Isoindolyl group, 6—Isoindolyl group, 7—Isoindol group Linole group, 2-Frinole group, 3-Frinole group, 2-Benzo'furaninole group, 3-Benzo'furaninole group, 4 Benzofuranino group, 5-Benzofuranore group, 6-Benzofuranore group, 7-Benzofuranore group Group, 1 isobenzofuranyl group, 3-isobenzofuranyl group, 4 isobenzofuranyl group, 5-isobenzofuran group Furanyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2 quinolinole group, 3 quinolinole group, 4-quinolinole group, 5 quinolinole group, 6 quinolinole group, 7 quinolyl group, 8-quinolinole group, 1 isoquinolinole group , 3-isoquinolyl group, 4 isoquinolinol group, 5 isoquinolinole group, 6 isoquinolinole group, 7 isoquinolinole group, 8 isoquinolinole group, 2 quinoxalinyl group, 5 quinoxalinyl group, 6 quinoxalinyl group, 1 one-strand rubazolyl group , 3-force rubazolyl group, 4 force rubazolyl group, 9 force rubazolyl group, 1 2-Nole group, 2-Atalidinyl group, 3-Atalidinyl group, 4-Ataridinyl group, 9-Atalidinyl group, 1,7 Phenanthroline 2-yl group, 1,7 Phenanthroline 3-3-yl group, 1, 7 Phenol Nanthroline 4-inole group, 1, 7 Phenylanthroline 5-inole group, 1, 7 Phenylthroline 6-yl group, 1, 7 Phenothroline 8-Inyl group, 1, 7 Phenothroline 9-Inole group, 1,7 phenanthroline 10-inole group, 1,8-phenanthroline-2 —yl group, 1,8-phenanthroline 3-yl group, 1,8-phenanthroline 4-yl group, 1,8- Phenanthroline-5-inore group, 1,8-phenanthroline-6-inore group, 1,8-phenanthroline-7-inore group, 1,8-phenanthroline-9-inore group, 1,8 — 10 phenanthroline, 1, 9 phenanthroline 1, 9 phenanthroline 3-ynole group, 1, 9 phenanthroline 4-inole group, 1, 9 phenanthroline-5-yl group, 1, 9 phenanthroline 1-6-yl group, 1, 9 7-yl group of phenanthroline, 1,9 phenanthroline-8-inore group, 1,9 phenanthroline 10-inole group, 1,10 phenanthroline 2-yl group, 1,10-phenanthroline 1-3 1, 10-phenanthroline 4-yl group, 1,10 phenanthroline 5-yl group, 2, 9 phenanthroline — 1-yl group, 2, 9 phenanthroline 3-yl group, 2, 9 phenanthroline 1 4-yl group, 2, 9 phenanthroline 5-yl group, 2, 9 phenanthroline 6-yl group, 2, 9 phenanthroline 7-inore group, 2, 9 phenanthroline 8-inole group, 2, 9 phenanthroline group 10 yl groups, 2, 8 phenanthroline 1 Group, 2, 8 phenanthrene 3 yl group, 2, 8 phenanthroline 4 yl group, 2, 8 phenanthroline 1 -5 yl group, 2, 8 phenanthroline 1 -6 yl group, 2, 8 Phenanthroline 7-yl group, 2, 8 Phenanthroline 1- 9 group, 2, 8 Phenanthroline 1- 10 group, 2, 7 Phenanthroline 1-inole group, 2, 7 Phenanthroline 3-inole group, 2, 7 4-phenyl group, 2,7-phenanthroline 5-yl group, 2,7-phenanthrolin--6-yl group, 2,7-phenanthroline 8-yl group, 2,7-phenanthroline-one 9-yl group, 2, 7 Phenanthroline 10-yl group, 1 Phenazinyl group, 2 Phenazinyl group Group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 10-phenothiazinyl group, 1 phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group , 4 phenoxazinyl group, 10-phenoxazinyl group, 2 oxazolyl group, 4 oxazolyl group, 5 oxazolyl group, 2 oxadiazolyl group, 5 oxadiazolyl group, 3 flazanyl group, 2 enyl group, 3 enyl group,

2 methyl pyrrole 1-yl group, 2 methyl pyrrole 1-yl group, 2 methyl pyrrole 1- 4-yl group, 2-methyl pyrrole 1-yl group, 2-methyl pyrrole 5-l group, 3-methyl pyrrole 1-yl group,

3 methyl pyrrole 2-yl group, 3 methyl pyrrole 4-yl group, 3 methyl pyrrole 5-nor group, 2-t-butyl pyrrole 4- 4-yl group, 3- (2 phenylpropynole) pyrrole 1-yl group, 2-methyl-1 indolyl group, 4-methyl-1 indolyl group, 2-methyl-3 indolyl group, 4-methyl-3 indolyl group, 2-t-butyl 1 indolyl group, 4 t-butyl 1 indolyl group, 2-t-butyl 3 indolyl group, 4 t Examples include butyl 3-indolyl group.

Examples of the aralkyl group include benzyl group, 1 phenylethyl group, 2-phenylchinole group, 1 phenylisopropyl group, 2-phenylisopropyl group, phenylol tertbutyl group, α naphthylmethyl group, 1 α naphthylethyl group, 2-α-naphthylethyl group, 1- / 3 naphthylethyl group, 2 / 3-naphthylethyl group, 1 β-naphthylisopropyl group, 2 βnaphthylisopropyl group, 1 pyrrolinoremethinole group, 2- (1 pyrrolyl) ethyl Group, ρ-methylbenzyl group, m-methylbenzyl group, o-methylbenzenole group, p-clobendinole group, m-clobendinole group, o-clobendinole group, p-bromobenzinole group, m-bromobenzenole group, o Bromobenzinole group, p-Chodobenzyl group, m-Chodobenzyl group, o-Codobenzyl group, p-Hydro Cybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzene Examples thereof include a benzyl group, a p-cyanobenzyl group, an m-cyanobenzyl group, an o-cyanobenzyl group, a 1-hydroxy-1-2-phenolinoisopropinole group, and a 1-chloro-1-2-phenolinoisopropinole group. The aryloxy group is represented as OZ, and examples of Z include phenyl group, 1 naphthanol group, 2 naphthino group, 1 linolinole group, 2 linolinole group, 9 nin linole group, 1 phenanthrinol group, 2 phenanthrinol group, 3 phenanthrinol group, 4 phenanthrinol group, 9 phenanthryl group, 1 naphthacenyl group, 2 naphthacenyl group, 9 naphthacenyl group, 1 —pyrenolinole group, 2 pyreninole group, 4 pyreninore group, 2 biphenylenoleore group, 3 Bifeninoreinore group, 4-Bifeninoreinore group, p-Terfeninole group 4-Inore group, p-Terfeninole group 3-inole group, p-Turpheninole group 2-inole group, m-Terfeninore 4-inole group, m-ter Pheninole 3inole group, m terfeninore 2inole group, o trinole group, m-trinole group, p trinole group, p-t Butylphenyl group, p- (2 phenylpropynole) phenyl group, 3 methyl-2-naphthyl group, 4-methyl-1 naphthyl group, 4-methinoleyl 1 antrinole group, 4'-methylbiphenylyl group, 4 "-tert-butyl-p-terphe 2-ruyl 4-yl group, 2-pyrrolyl group, 3 pyrrolyl group, pyradyl group, 2 pyridinyl group, 3 pyridinyl group, 4 pyridinyl group, 2 indolinole group, 3 indolinole group, 4 indolinole group, 5 indolinole group, 6 indolyl group, 7 indolyl group, 1 isoindolyl group, 3 isoindolyl group, 4-soindolyl group, 5 isoindolyl group, 6 isoindolyl group, 7 isoindolyl group, 2—furinole group, 3 frinole group, 2 benzofuranyl group, 3 benzofuranyl group, 4 Benzofuran group, 5 benzofuranyl group, 6 benzofuranyl group, 7 Zofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group, 4 isobenzofuranyl group, 5-isobenzazofuranyl group, 6 isobenzofuranyl group, 7 isobenzofuranyl group, 2 quinolyl group, 3-quinolinole group, 4-quinolinole group, 5-quinolinole group, 6-quinolinole group, 7-quinolinole group, 8-quinolinole group, 1 isoquinolinole group, 3-isoquinolyl group, 4 isoquinolinole group, 5-isoquinolyl group, 6 isoquinolyl group, 7 isoquinolyl group , 8 Isoquinolyl group, 2 Quinoxalinyl group, 5 Quinoxalinyl group, 6 Quinoxalinyl group, 1 Force rubazolyl group, 2 Force rubazolinole group, 3 Force rubazolyl group, 4 Force rubazolyl group, 1 Phenylanthridinyl group, 2 Phenylanthridinyl Group, 3-phenanthridinyl group, 4 phenanthridinyl group, 6-phenance Lysinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1 attaridinyl group, 2-atalidinyl group, 3--ataridinyl group, 4-atalidinyl group Group, 9-Ataridinyl group, 1, 7 phenanthroline-2 —Yl group, 1, 7 phenanthroline 1 3-yl group, 1, 7 phenanthroline 1 4-yl group, 1, 7 phenanthroline-5-inore group, 1, 7 phenanthroline-6-inore group, 1, 7 — Phenylanthroline-8-inore group, 1, 7 Phenothroline-9-inore group, 1,7 Phenothroline 1-10-yl group, 1,8 Phenothroline 1-2-yl group, 1,8 Phenothroline 3-inole group 1,8-phenanthroline-4-ynole group, 1,8-phenanthroline-5-yl group, 1,8-phenanthroline-6-yl group, 1,8-phenanthroline-1-yl group, 1,8-Phenanthhroline-9-inole group, 1,8-Phenanthroline 10--inole group, 1,9 Phenanthroline 1- 2-yl group, 1,9 Phenanthroline 3-3-yl group, 1,9 Phenanthroline 1 4-yl group, 1, 9-phenanthroline 1-5-yl group, 1, 9-hue 1-Nylthroline 6—yl group, 1,9 Phenylthroline 1-7-yl group, 1,9 Phenylthroline 1-8-yl group, 1,9 Phenylthroline 10-inole group, 1,10 Phenylthroline 2-inole group, 1, 1 0 Phenanthroline-3, 1-group, 1, 10 Phenanthroline, 1-yl group, 2, 9 Phenanthroline, 1- 10 groups Group, 2, 9 phenanthroline 1 4 yl group, 2, 9 phenanthroline 1 -5 group, 2, 9 phenanthroline 1 6 yl group, 2, 9 phenanthroline 1 -7 yl group, 2, 9 phenanthroline 1 -8 —Yl group, 2, 9 phenanthroline 1-10—yl group, 2,8 phenanthroline 1-inole group, 2,8 phenanthroline 3-inole group, 2,8 phenanthroline 4-yl group, 2,8 phenanthroline 1-5 Group, 2, 8 Hue Nthroline 6—yl group, 2, 8 phenanthroline 7—yl group, 2, 8 phenanthroline 9—yl group, 2, 8—phenanthroline 10 yl group, 2, 7 phenanthroline 1—yl 2, 7 phenanthroline 3-yl group, 2, 7 phenanthroline 4-yl group, 2, 7 phenanthroline 5-yl group, 2, 7 phenanthroline 6-yl group, 2, 7 phenanthroline 8-inole Group, 2, 7 phenanthroline 9-yl group, 2, 7 phenanthroline 1- 10 yl group, 1 phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 1 phenoxazinyl group, 2 phenoxazinyl group, 3 phenoxazinyl group, 4 phenoxazinyl group, 2 oxazolyl group, 4-oxazolyl group, 5 oxazolyl group, 2 Kisajiazoriru group, 5 Okisajiazoriru group, 3 furazanyl, 2-thienyl group, 3-thienyl group, 2 1-methyl group, 2-methylpyrrole 3-yl group, 2-methylpyrrole 4-reinyl group, 2-methylpyrrole 5-yl group, 3 methyl-pyrrole 1-yl group, 3 methyl-pyrrole 2-yl group 4-methyl group, 3-methylpyrrole 4-yl group, 3-methylpyrrole-noryl 5-inol group, 2-t-butyl pyrrole 4-yl group, 3-(2 phenylpropinole) pyrrole 1-yl group, 2-methyl-1-indolyl group, 4-methyl-1 indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl 1 indolyl group, 4 t-butyl 1 indolyl group, 2-t-butyl 3-indolyl group, 4 t-butyl 3-indolyl group Groups and the like.

The alkoxy carbonyl group is expressed as COOY, and Y is, for example, methyl group, ethyl group, 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, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutynole group, 1,2-dihydroxyethyl group, 1 , 3-Dihydroxyisopropyl group, 2,3-dihydroxyt-butyl group, 1,2,3 trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chlorodiethyl group, 2-cyclodiethyl Isobutyl group, 1,2-dichlorodiethyl group, 1,3-dichlorodiethyl group, 2,3-dichloro-butyl group, 1,2,3 trichloropropyl group, bromomethyl group, 1 bromoethyl group, 2-bromo group Tyl group, 2-bromoisobutyl group, 1,2 dibromoethyl group, 1,3 dibromoisopropyl group, 2,3 dib mouth tert-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl, 2-iodoisobutyl, 1,2-jodoethyl, 1,3-jodoisopropinole, 2,3 joad toff, chinole, 1,2,3 triode Propinole group, aminomethyl group, 1 aminoethynole group, 2-aminoethynole group, 2-aminoisobutyl group, 1,2 diaminoethyl group, 1,3 diaminoisopropyl group, 2,3 diamino-tbutyl group, 1, 2,3-triaminopropyl group, cyanomethylol group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-discyanoethyl group, 1,3-discyanoisopropyl group, 2, 3 disianol t-butyl group, 1, 2, 3 tricyanopropyl group, nitromethyl group, 1-12 troethyl group, 2-ditroethyl group, 2-ditroisobutyl group, 1,2-dinitrobutynole group, 1, 3- Ginny mouth isopropinole group, 2, 3—Ginny low toff “Tinole group, 1, 2, 3— A trinitropropyl group etc. are mentioned.

In addition, the above substituents may be bonded to each other to form a ring. Examples of the divalent group that forms a ring include a tetramethylene group, a pentamethylene group, a hexamethylene group, and a diphenylmethane. 2, 2 'diyl group, diphenylethane 3, 3' diyl group, diphenyl pour pan 4, 4 'diyl group and the like.

[0025] Specific structures of the compound represented by the general formula (1) of the present invention include the following structures. This is because forces Ar ¹ and Ar ² that have a structure with Cz in the part corresponding to ΑΛ Ar ² contain Cz. In the following structure, the phenyl moiety and the thiophene moiety may be substituted with an alkyl group or an aryl group having 6 to 10 carbon atoms.

[0026] [Chemical 5]

1

Specific examples of the compound represented by the general formula (1) in the present invention are shown below, but are not limited to these exemplified compounds.

[Chemical 6] / v: / O I9sp0 / -00ifcl £ 8ε / -0800ίAV

Star s

/ v: / O I9sp0 / -00ifcl £ 8 £ si / -0800iAV ^

[0030] [Chemical 9] / v: / O I9sp0 / -00ifcl £ 8ε / -0800ίAV 93

§Ϊ́0ε

The dopant used in the light emitting layer of the organic EL device of the present invention is composed of a metal complex compound represented by the following general formula (a) and / or (b).

[Chemical 11]

In the general formulas (a) and (b), R to R each independently represent a hydrogen atom, a cyan group,

1 7

Nitro group, halogen atom, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted amino group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted An alkylsilyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon number;! To a 20 acyl group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted carbon number Represents 3 to 30 aromatic heterocyclic groups. Also, among R ~ R

1 7 Adjacent ones are bonded together to form a ring structure.

Examples of the halogen atom include fluorine, chlorine, bromine and iodine power. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, and an isopropylene group. Group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group and the like.

The alkoxyl group is represented as OY, and Y includes the same as those mentioned for the alkyl group.

Examples of the alkylsilyl group include a trimethylsilyl group and a t-butyldimethylsilyl group.

Examples of the acyl group include an acetyl group, a propionyl group, a butyryl group, and an isobutyryl group.

Examples of the aromatic hydrocarbon group and the aromatic heterocyclic group include benzene, naphthalene, anthracene, phenanthrene, pyrene, coronene, biphenyl, terphenyl, pyromonore, furan, thiophene, benzothiophene, oxadiazoline, and diene. Examples thereof include residues such as phenylenoanthracene, indoline, carbazole, pyridine, benzoquinone, fluoranthene, and isenaftfluoranthene.

[0034] The substituents of these groups include cyano group, hydroxyl group, nitro group, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted amino group, substituted or unsubstituted alkoxyl group. Substituted or unsubstituted alkylsilyl group, substituted or unsubstituted acyl group, substituted or unsubstituted aromatic group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted A heterocyclic group, a substituted or unsubstituted aryloyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, a carboxyl group, and the like.

Examples of the ring structure formed by bonding adjacent R to R include, for example, ben

1 7

Zen, pyridine, naphthalene, benzothiazole, quinoline and the like.

More specific ring structures include R and R, R and R, or R and R, and R

1 2 2 3 3 4 1 ~ R is

4 As R to R in the ring structure formed with the bonded benzene ring,

14

The divalent group represented by these is mentioned, BL, MES1, MES2, PS1, and PS2 are preferable.

[0035] [Chemical 12] CH2CH2CH2CH2-- CH5CH9CH2 --- CH2OCH2CH2 ---- CH ₂ CH ₂ OCH _2-

B L P L MEE 1 MEE 2

^ OCH ₂ CH ₂ CH ₂ — — CH ₂ CH ₂ CH ₂ 0— ~ OCH ₂ CH ₂ — — CH ₂ CH ₂ 0- PA 1 P A2 EA 1 KA 2

—— CH ₂ OCH ₂ — ~~ OCH ₂ 0— — CH ₂ SCH ₂ CH ₂ — — CH ₂ CH ₂ SCH ₂ —

ME AT ME S 1 ME S 2

― CCH ₂ CH ₂ CH ₂ —— —— CH ₂ CH ₂ CH ₂ C—

— SCHsCn CH— — CH2CH2CH2S—

0 O

P S 1 P S 2 BAL I BAL 2

-CH2CCH2CH2——-C H2C H2C CH 2— —— CCH ₂ CH ₂ --CH2CH2C- 0 OOO

MEK 1 MEK 2 PAL PAL 2

-CH2CCH2- -COCH2CH2- — CH ₂ CH ₂ OC- -CCH ₂ CH ₂ 0- O o OO

MMK EE S EE S 2 P AE

_{_{_{^ OCH 2 CH 2 C- -CH 2}}} COCH 2 - - CH 2 OCCH 2 - - CCH2OCH2 one

O O O

P AE 2 AME AME 2 E AE

-CH2OCH2C- -CH ₂ CCH ₂ 0- — OCH ₂ CCH ₂ — -CH2CH2CO- OOOO

E AE 2 AAE 1 AAE 2 PME 1

_{_{^ OCCH 2 CH 2 - - COCH2-}} ~ CH 2 co- CCH 2 o- II II

O o 0 0

PME 2 ME S 1 ME S 2 EE

OCCH ₂ --CH ₂ OC—— ~ OCH ₂ C—

II

o O o

EE 2 MS MS 2 In general formulas (a) to (b), R to R and R are hydrogen atoms, and R, R, and R are each independently substituted or unsubstituted carbon atoms of 6 to 6 30 aromatic hydrocarbon groups or substitutions Alternatively, it is preferably an unsubstituted aromatic heterocyclic group having 6 to 30 carbon atoms.

In the general formulas (a) to (b), R to R and R are hydrogen atoms, and R and R 1 respectively

Independently, it is preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms or a substituted or unsubstituted aromatic heterocyclic group having 6 to 30 carbon atoms.

In general formulas (a) to (b), R 1, R and R are

1 to R and R are hydrogen atoms

4 7 5 6 Each independently is preferably a substituted or unsubstituted phenyl group, naphthyl group, biphenyl group, tertphenyl group, quarterphenyl group, phenanthrenyl group or triphenylenyl group.

Further, in general formula (a), R

1 to R is a hydrogen atom, R is unsubstituted or has 1 carbon

4 5

A phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a phenanthrenyl group, or a triphenylenyl group having -30 substituents, and R

It is preferable that each of 6 to R is independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms or an alkyl group having 1 to 10 carbon atoms or an aromatic hydrocarbon group having 10 to 10 carbon atoms.

In general formulas (a) and (b), M is a metal atom of iridium (Ir), rhodium (Rh), platinum (Pt) or palladium (Pd), and Ir and Pt are preferred. Ir is more preferred. .

In the general formulas (a) and (b),! /, N is an integer of! ~ 3, preferably 2 ~ 3! /.

In general formulas (a) and (b), n = 3 when M is Ir.

Specific examples of the compound represented by the general formula (a) are shown below, but are not limited to these exemplified compounds.

[Chemical 13]

Specific examples of the compound represented by the general formula (b) are shown below, but are not limited to these exemplified compounds.

[Chemical 14]

Hereinafter, the organic EL device of the present invention will be described.

The organic EL device of the present invention is a device in which one or more organic thin film layers are formed between the anode and the cathode as described above. In the case of a single layer type, a light emitting layer is provided between the anode and the cathode. The light emitting layer contains a light emitting material, and in addition, may contain a hole injecting material or an electron injecting material in order to transport holes injected from the anode or electrons injected from the cathode to the light emitting material. . In addition, the light emitting material preferably has a very high fluorescence quantum efficiency, a high hole transport capability and an electron transport capability, and forms a uniform thin film. Multi-layer type organic EL devices include (Anode / Hole injection layer / Light emitting layer / Cathode), (Anode / Light emitting layer / Electron injection layer / Cathode), (Anode / Hole injection layer / Light emitting layer / Electron injection layer) / Cathode) etc. are stacked in a multilayer structure.

[0040] In addition to the host material of the general formula (1) of the present invention and the dopant of the general formula (a) and / or (b), the light emitting layer may further include a known host material, a light emitting material, A doping material, a hole injection material, or an electron injection material may be used and used in combination. The organic EL element has a multi-layer structure, which can prevent the brightness and lifetime from decreasing due to quenching, improve the light emission brightness and light emission efficiency, and use it in combination with other doping materials that contribute to phosphorescence emission. Therefore, the power S can be improved by improving the conventional luminance and luminous efficiency.

In addition, the hole injection layer, the light emitting layer, and the electron injection layer in the organic EL device of the present invention may each be formed with a layer structure of two or more layers. At that time, in the case of the hole injection layer, the layer that injects holes from the electrode is called the hole injection layer, and the layer that receives holes from the hole injection layer and transports the holes to the light emitting layer is called the hole transport layer. . Similarly, in the case of an electron injection layer, a layer for injecting electrons from an electrode is called an electron injection layer, and a layer for receiving electrons from the electron injection layer and transporting electrons to a light emitting layer is called an electron transport layer. Each of these layers is selected and used depending on factors such as the energy level of the material, heat resistance, adhesion with the organic thin film layer or the metal electrode.

[0041] Examples of the luminescent material or host material that can be used in the organic thin film layer together with the compound represented by the general formula (1) and the general formula (a) and / or (b) used in the present invention include anthracene, naphthalene, phenanthrene, and pyrene. , Tetracene, Coronene, Talycene, Funoleic Recein, Perylene, Perforated Perylene, Naphtal Perylene, Perinone, Perforated Perinone, Naphtal Perylene, Diphenylbutadiene, Tetraphenylbutadiene, Coumarin, Metaphenylene Compound, Benzofuran Derivative Benzothiophene derivatives, arylene silane compounds, pyridine ring-containing compounds, pyrimidine ring-containing compounds, triazine ring-containing compounds, triphenylene compounds, quinoxaline compounds, oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine, cyclopentadiene Quinoline metal complex, aminoquinoline metal complex, benzoquinoline metal complex, imine, diphenylethylene, buranthracene, diaminoanthracene, diaminocarbazole, pyran, thiopyran, polymethine, merocyanine, imidazole chelated oxinoid compound, quinacridone, Forces including rubrene, stilbene derivatives and fluorescent dyes, but are not limited thereto. In addition, as a light emitting material, a metal atom of an organometallic complex which is preferably a phosphorescent organometallic complex in that the external quantum efficiency of the element can be further improved is ruthenium, rhodium, palladium, silver, rhenium. , Osmium, iridium, platinum, gold, copper and the like.

[0042] As a hole injection material, it has the ability to transport holes, the effect of hole injection from the anode, A compound having an excellent hole injection effect for the light emitting layer or the light emitting material, preventing the excitons generated in the light emitting layer from moving to the electron injection layer or the electron injecting material, and having an excellent thin film forming ability is preferable. . Specifically, phthalocyanine derivatives, naphthalocyanine derivatives, phenolephrine derivatives, oxazonole, oxadiazole, triazonole, imidazolone, imidazolone, imidazoline, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole, hydrazone, and acylhydrazone , Polyarylalkanes, stilbenes, butadienes, benzidine type triphenylamines, starburst type amines, triarylamines, and their derivatives, hexaazatriphenylene derivatives, styrylamine type triphenylamines, diamine type triphenylamines. And the like, and derivatives thereof, and polymer materials such as polycarbcarbazole, polysilane, and conductive polymer, but are not limited thereto. There.

[0043] Among these hole injection materials, more effective hole injection materials are aromatic tertiary amine derivatives or phthalocyanine derivatives. Specific examples of aromatic tertiary amine derivatives include triphenylenoamine, tritrinoleamine, tolyldiphenylamine, N, N, one diphenylamine, N, N, one (3-methylphenyl) one. 1, 1, 1 biphenyl 1, 4, 1 diamine, N, N, Ν ', 1, 1 (4-methylphenyl) 1 1, 1, 1 phenenole 1, 4, 1 diamine,, Ν, Ν,, Ν, One (4-methylphenyl) 1, 1, 1, One biphenyl 1, 4, 4, One Diamine, 4, 4,, 4 "—Tri (Ν-carbazolyl) Triphenylamine, Ν , Ν, 1 Diphenyl 1 Ν, Ν'—Dinaphthyl 1, 1 '— Biphenyl 2 4, 4, 1 Diamine, Ν, Ν,-(Methylphenyl) Ν, Ν,-(4— η Butylphenyl) 1 Phenanthrene 9, 10 Diamine, Ν, Ν Bis (4 Di-4-Trirylaminophenyl) -4 Phenylcyclohexane etc., or aromatics thereof Is not limited that the force to these oligomers or polymers having a tertiary amine bone skeleton. Examples of full Taroshianin (p _c) derivatives, H Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, CllnPc, ClSnPc, CI SiPc, (HO) AlPc, (H ○) Phthalocyanine derivatives such as GaPc, VOPc, TiOPc, MoOPc, GaPc—O—GaPc, and force S that are naphthalocyanine derivatives. It is not limited.

[0044] The electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect on the light emitting layer or light emitting material, and excitation generated in the light emitting layer. A compound that prevents migration of the child to the hole injection layer and has an excellent thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, triphenylene, polyphenylene, oxazole, oxaziazole, triazonole, imidazole, perylenetetracarboxylic acid, quinoxaline, fluorenylidenemethane, anthraquinodimethane, anthrone, etc. And the powers of their derivatives are not limited to these.

Among these electron injection materials, more effective electron injection materials are metal complex compounds or nitrogen-containing five-membered ring derivatives. Specific examples of metal complex compounds include lithium 8-hydroxyquinolinate, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] quinolinato) beryllium, bis (10 hydroxy Benzo [h] quinolinato) zinc, bis (2-methyl-8 quinolinato) chlorogallium, bis (2-methyl-8 quinolinato) (o cresolate) gallium, bis (2-methyl-8 quinolinato) (1 naphtholato) aluminum, bis (2 —Methyl-8 quinolinate) (2-naphtholato) gallium, etc. Including but not name limited thereto.

Further, the nitrogen-containing five-membered derivative is preferably an oxazole, thiazole, oxadiazole, thiadiazole or triazole derivative. Specifically, 2,5 bis (1-phenyl) -1,3,4-oxazole, dimethyl POPOP, 2,5-bis (1-phenyl) 1,3,4, thiazole, 2, 5 Bis (1-phenyl) 1, 3, 4 oxadiazole, 2- (4'-tert butylphenyl) -5- (4 "-biphenyl) 1, 3, 4 oxadiazole, 2, 5 Bis (1-naphthyl) 1,3,4 oxadiazole, 1,4 bis [2— (5 phenoxadiazolyl)] benzene, 1,4 bis [2— (5 phenyloxadiazolyl) 4 — tert butyl Benzene], 2-(4'- tertbutylphenyl) 1-5- (4 "biphenyl)-1, 3, 4 thiadiazole, 2,5 bis (1 naphthyl) 1, 3, 4 thiadiazone, 1, 4 Bis [2— (5 phenylthiazolyl)] benzene, 2— (4,1 tert-butylphenol) 1-5— (4,1, biphenyl) 1,3,4 Triazolene, 2,5 Bis (1 —Naph Chill) 1,3,4-triazolene, 1,4-bis [2- (5-phenyltriazolyl)] benzene, and the like.

The charge injection property can also be improved by adding an electron accepting material to the hole injecting material and an electron donating material to the electron injecting material.

[0046] As the conductive material used for the anode of the organic EL device of the present invention, a material having a work function larger than 4 eV is suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, Silver, gold, platinum, palladium and the like and alloys thereof, metal oxides such as tin oxide and indium oxide used for ITO substrates and NES A substrates, and organic conductive resins such as polythiophene and polypyrrole are used. As the conductive material used for the cathode, those having a work function smaller than 4 eV are suitable. Magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, etc. and their alloys The force used is not limited to these. Alloys include, but are not limited to, forces S, such as magnesium / silver, magnesium / indium, lithium / aluminum, and the like. The ratio of the alloy is controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, etc., and is selected to an appropriate ratio. The anode and cathode may be formed with a layer structure of two or more layers if necessary! /!

[0047] The organic EL device of the present invention has an inorganic compound layer between at least one of the electrodes and the organic thin film layer. Preferred for use in inorganic compound layers! /, Inorganic compounds include alkali metal oxides, alkaline earth oxides, rare earth oxides, alkali metal halides, alkaline earth halides, rare earth halides, SiO, AIO , SiN, SiON

X X X

A10N, GeO, LiO, LiON, TiO, TiON, TaO, TaON, TaN, C, etc.

X X X X X

Oxides, nitrides, and oxynitrides. In particular, as the component of the layer in contact with the anode, SiO, A

X

lO, SiN, SiON, A10N, GeO, and C are preferable because they form a stable injection interface layer. Ma

X X X

In particular, LiF, MgF, CaF, MgF, and NaF are preferred as the components of the layer in contact with the cathode.

[0048] In order for the organic EL device of the present invention to emit light efficiently, it is desirable that at least one surface be sufficiently transparent in the light emission wavelength region of the device. It is also desirable that the substrate be transparent. The transparent electrode is set so that a predetermined translucency is secured by a method such as vapor deposition or sputtering using the above conductive material. The electrode on the light emitting surface is desirable to have a light transmittance of 10% or more. The substrate is not limited as long as it has mechanical and thermal strength and has transparency, and examples thereof include a glass substrate and a transparent resin film. Examples of the transparent resin film include polyethylene, ethylene acetate butyl copolymer, ethylene-butyl alcohol copolymer, polypropylene, polystyrene, polymethyl methacrylate, polychlorinated butyl, polybutyl alcohol, polybutyl butyral, nylon, Polyetheretherketone, Polysulfone, Polyethersulfone, Tetrafluoroethylene perfluoroalkyl butyl ether copolymer, Poly fluoride, Tetrafluoroethylene ethylene copolymer, Tetrafluoroethylene xafluoropropi Examples include lene copolymer, polychloroethylene, polyvinylidene fluoride, polyester, polycarbonate, polyurethane, polyimide, polyetherimide, polyimide, and polypropylene. .

The organic EL device of the present invention can be provided with a protective layer on the surface of the device or to protect the entire device with silicon oil, resin, etc. in order to improve stability against temperature, humidity, atmosphere, etc. is there.

For the formation of each layer of the organic EL device of the present invention, any of dry film forming methods such as vacuum deposition, sputtering, plasma, ion plating, etc. and wet film forming methods such as spin coating, dating, and floating are applied. can do. The thickness of each layer is not particularly limited, but should be set to an appropriate thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor luminous efficiency. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied. The normal film thickness is in the range of 51 111 10 111. The force in the range of 10 nm to 0.2 111. Force S is more preferable.

In the case of the wet film forming method, the material for forming each layer is dissolved or dispersed in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane or the like to form a thin film, but any solvent may be used. . In any layer, an appropriate resin or additive may be used to improve film formability and prevent pinholes in the film. As usable resin Insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyuretan, polysulfone, polymethylmetatalylate, polymethyl acrylate, and cellulose, and their copolymers, poly N-butylcarbazole, polysilane And photoconductive resins such as polythiophene and polypyrrole. Examples of the additive include an antioxidant, an ultraviolet absorber, and a plasticizer.

Example

Hereinafter, the present invention will be described in more detail with reference to examples. However, the present invention is not limited to the following examples as long as the gist thereof is not exceeded.

Example 1 (Production of organic EL device)

A glass substrate (manufactured by Zomatic Co., Ltd.) having a thickness of 25 mm × 75 mm × l. 1 mm with an ITO transparent electrode 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 cleaning is mounted on the substrate holder of the vacuum evaporation system. First, an HTM with a film thickness of 95 nm is placed on the surface where the transparent electrode line is formed so as to cover the transparent electrode. (See the structural formula below). The HTM film functions as a hole injection transport layer. Further, following the formation of the hole injecting and transporting layer, (43) as a host compound and complex (A4) as a dopant were co-deposited by resistance heating on the film with a thickness of 30 nm. The concentration of complex (A4) was 7.5 wt%. This host compound: (43) film functions as a light emitting layer. Subsequent to the formation of the light emitting layer, the following material ETM1 was deposited to a thickness of 25 nm, and the following material ETM2 was deposited to a thickness of 5 nm on the ETM1. The ETM1 layer and ETM2 layer function as an electron transport layer and an electron injection layer. Thereafter, Li F was used as an electron injecting electrode (cathode) to form a film thickness of 0.1 nm at a film forming speed of 1 A / min. Metal A1 was vapor-deposited on this LiF layer, and a metal cathode was formed to a thickness of 150 nm to form an organic EL device.

(Emission performance evaluation of organic EL elements)

The organic EL device fabricated as described above is caused to emit light by direct current drive (current density = ImA / cm ² ), and the external quantum efficiency (%) and luminance (U are measured, and the luminous efficiency (L / J) is determined. The results are shown in the following Table 1. The half-life measured at an initial luminance of 1500 cd / m ² is also shown. [0051] [Chemical 15]

[0052] Examples 2-8

In Example 1, the same procedure was used except that the combinations of the compounds described in the host compound column and dopant column of Table 1 were used instead of the combination of host compound (43) and complex (A4). Machine EL device was manufactured. Table 1 shows the results of evaluating each organic EL element obtained in the same manner as in Example 1.

[0053] Comparative Example;! ~ 5

[Chemical 16]

HostQ

[0054] [Table 1] table 1

Industrial applicability

As described above in detail, the organic EL device of the present invention has high emission luminance and light emission efficiency free from pixel defects, and has a long lifetime. This organic EL device is, for example, an electrophotographic photosensitive member, a flat light emitter such as a flat panel display for a wall-mounted television, a light source such as a copying machine, a printer, a backlight of a liquid crystal display or an instrument, a display board, a marker lamp, and an accessory. Etc. are preferably used.

Claims

Claims In an organic electroluminescence device in which an organic thin film layer composed of one layer or a plurality of layers is sandwiched between a cathode and an anode, the compound represented by the following general formula (1) is used as a host material, and the following general An organic electoluminescence device containing a metal complex compound represented by the formula ω and / or (b) as a dopant.

[Chemical 1]

(In the formula, Cz is a carbazolyl group, an 18 to 60 carbonyl carbazolyl group, an azacarbazolyl group, an allylazazacarbazol group having 18 to 60 carbon atoms, an atalidinyl group, a phenoxazinyl group, or a dibenzozepinyl group. Ar ¹ and Ar ² are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted carbon atom having 3 to 60 carbon atoms. Ar ³ is an aromatic hydrocarbon group having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 60 carbon atoms Ar ⁴ is a substituted or unsubstituted heterocyclic group. A benzene residue, a substituted or unsubstituted thiophene residue, a substituted or unsubstituted triazole residue, a substituted or unsubstituted fluorene residue, or a substituted or unsubstituted spirobifluorene residue.

a is 0 ;! integer, b is an integer of 0 to 4, c is !; an integer of 1-3, when Cz and Ar ⁴ is more may respectively be the same or different from each other.

However, & = 0. When = 1, Ar ³ and Ar ⁴ are benzene residues, and Ar ^{2 is a} phenylcarbazolyl group or carbazolyl group. In addition, when _a = l, b = 0 and c = 1, Ar "is a benzene residue and Ar ¹ and Ar ² are phenylcarbazolyl groups. Further, b = 0 and c = When l = Ar ³ is a benzene residue and Ar ¹ , Ar ² and Cz are carbazolyl groups or phenylcarbazolyl groups)

[Chemical 2]

(In the general formulas (a) and (b), R to R each independently represent a hydrogen atom, a cyan group,

1 7

n is an integer from!

However, when M is Ir, n = 3. )

The organic electroluminescent element according to claim 1, wherein (Ar ⁴ ) b is represented by the following formula in the general formula (1).

[Chemical 3]

Or

(In the formula, Ar ⁵ and Ar ⁶ are each independently the same as Ar ⁴ , and d is an integer of 0 to 3.

When there are a plurality of Ar ^{5 s} , they may be the same or different. )

[3] The organic electroluminescence device according to claim 1, wherein a = 0 in the general formula (1).

[4] The organic electroluminescent device according to claim 1, wherein a = 0 and b = 0 in the general formula (1).

[5] In the general formula (1), Α ~Α Γ _⁴ An organic elect opening device according to claim 1 respectively an aromatic hydrocarbon group.

[6] In general formula (1), when a = b = l and c = 2, Ar ¹ and Ar ² are each a phenyl group, Ar

2. The organic electroluminescent element according to claim 1, wherein ³ is a phenyltolyl group, and Ar ⁴ is a phenylene group.

[7] The organic electoluminescence device according to [1], wherein in the general formula (1), a = 0, b = 0, and c = 2 to 3.

8. The organic electroluminescent device according to claim 1, wherein in the general formulas (a) to (b), M is iridium (Ir) or platinum (Pt).

[9] In the general formulas (a) to (b), R to R and R are hydrogen atoms, and R, R and R forces

1 3 7 4 5 6 Each independently is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms or a substituted or unsubstituted aromatic heterocyclic group having 6 to 30 carbon atoms. The organic electroluminescent element described in 1.

[10] In the general formulas (a) to (b), R to R and R are hydrogen atoms, and R and R 1 respectively

1 4 7 5 6 is independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms or a substituted or unsubstituted aromatic heterocyclic group having 6 to 30 carbon atoms. The organic elect mouth luminescence element of description.

[11] In the general formulas (a) to (b), R to R and R are hydrogen atoms, and R and R 1 respectively

14. The method according to claim 1, which is independently a substituted or unsubstituted phenyl group, naphthyl group, biphenyl group, terphenyl group, quarterphenyl group, phenanthrenyl group or triphenylenyl group. Organic electoluminescence element.

[12] In general formula (a), R to R are hydrogen atoms, R is unsubstituted or has carbon number; A substituted phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a phenanthrenyl group, or a triphenylenyl group, and R to R each independently represent a hydrogen atom or a carbon number of 1 to; 2. The organic electoluminescence device according to claim 1, which is an alkyl group having 10 carbon atoms or an aromatic hydrocarbon group having 1 to 10 carbon atoms.