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US 2016/0322587 A1Published application
Condensed fluoranthene compound, material for organic electroluminescent element using this compound, organic electroluminescent element using this material, and electronic device
AssigneeIdemitsu Kosan Co., Ltd.
InventorsMasahiro KAWAMURA, Kazuki NISHIMURA
Life of this patent
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Abstract
A fused fluoranthene compound which includes an indeno[3,2-b]fluoranthene skeleton having a hetero atom is a novel compound, which is useful as a material for organic electroluminescence devices for use in an organic electroluminescence device and an electronic equipment.
Claims24
1:
- An organic electroluminescence device, comprising:
- a cathode;
- an anode;
- and
- an organic thin film layer comprising one or more layers disposed between the cathode and the anode,
- wherein the organic thin film layer comprises a light emitting layer and at least one layer of the organic thin film layer comprises a fused fluoranthene compound represented by formula (a):
- wherein:
- Xa represents Si(R13)(R14), a sulfur atom, or an oxygen atom;
- and
- each of R1a to R14a independently represents a hydrogen atom or a substituent, and adjacent groups of R1a to R14a may be bonded to each other to form a saturated or unsaturated ring structure.
7 more elements
2:
- The organic electroluminescence device according to claim 1, wherein the fused fluoranthene compound is represented by formula (b):
- wherein:
- Xb represents Si(R3b)(R14b), a sulfur atom, or an oxygen atom;
- each of R1b to R14b independently represents, a hydrogen atom, a substituent, or a bond to Lb, and adjacent groups of R1b to R14b may be bonded to each other to form a saturated or unsaturated ring structure;
- and
- Lb represents a single bond or a divalent linking group.
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3:
- The organic electroluminescence device according to claim 1, wherein the fused fluoranthene compound is represented by formula (c):
- wherein:
- Xc represents Si(R13c)(R14c), a sulfur atom, or an oxygen atom;
- each of R1c to R14c independently represents a hydrogen atom, a substituent, or a bond to Lc, and adjacent groups of R1c to R14c may be bonded to each other to form a saturated or unsaturated ring structure;
- Yc represents a substituted or unsubstituted p-valent aromatic hydrocarbon group having 6 to 60 ring carbon atoms or a substituted or unsubstituted p-valent heterocyclic group having 3 to 60 ring atoms;
- Lc represents a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 3 to 60 ring atoms, or a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms;
- and
- p represents an integer of 1 to 6.
5 more elements
4:
- The organic electroluminescence device according to claim 1, wherein the fused fluoranthene compound is represented by formula (d):
- wherein:
- Xd represents Si(R13d)(R14d), a sulfur atom, or an oxygen atom;
- each of R1d to R14d independently represents a hydrogen atom, a substituent, or a bond to Ld, and adjacent groups of R1d to R14d may be bonded to each other to form a saturated or unsaturated ring structure;
- and
- Ld represents a trivalent organic group.
3 more elements
5:
- The organic electroluminescence device according to claim 1, wherein at least one of R1a to R14a of formula (a) represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, an amino group, a mono- or disubstituted amino group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
6:
- The organic electroluminescence device according to claim 5, wherein the aryl group having 6 to 50 ring carbon atoms is a phenyl group, a naphthyl group, a naphthylphenyl group, a biphenylyl group, a terphenylyl group, an acenaphthylenyl group, an anthryl group, a benzanthryl group, an aceanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a fluorenyl group, a 9,9′-spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a picenyl group, a pentaphenyl group, a pentacenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a s-indacenyl group, an as-indacenyl group, a fluoranthenyl group, a benzofluoranthenyl group, a tetracenyl group, a triphenylenyl group, a benzotriphenylenyl group, a perylenyl group, a coronyl group, or a dibenzanthryl group.
7:
- The organic electroluminescence device according to claim 5, wherein the heteroaryl group having 5 to 50 ring atoms is a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group, an isooxazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a tetrazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, an isobenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, an indolizinyl group, a quinolizinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, an indazolyl group, a benzisoxazolyl group, a benzisothiazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a phenothiazinyl group, a phenoxazinyl group, an azatriphenylenyl group, a diazatriphenylenyl group, a xanthenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, a benzofuranobenzothiophenyl group, a benzothienobenzothiophenyl group, a dibenzofuranonaphthyl group, a dibenzothienonaphthyl group, or a dinaphthothienothiophenyl group.
8:
- The organic electroluminescence device according to claim 5, wherein the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms is a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, or an octadecyl group.
9:
- The organic electroluminescence device according to claim 5, wherein the mono- or di-substituted amino group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms has the alkyl and aryl substituents which are selected from the alkyl groups and the aryl groups described in claims 6 and 8.
10:
- The organic electroluminescence device according to claim 1, wherein each of R1a to R14a of formula (a) independently represents a hydrogen atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a s-butyl group, a t-butyl group, a phenyl group, a naphthyl group, a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.
11:
- The organic electroluminescence device according to claim 1, wherein Xa of formula (a) represents an oxygen atom.
12:
- The organic electroluminescence device according to claim 1, wherein Xa of formula (a) represents a sulfur atom.
13:
- The organic electroluminescence device according to claim 5, wherein R3a of formula (a) has the substituent, and each of R1a, R2a, R4a, R5a, R6a, R7a, R8a, R9a, R10a, R11a and R12a of formula (a) is a hydrogen atom.
14:
- The organic electroluminescence device according to claim 5, wherein R1a and R2a of formula (a) are bonded to each other to form a benzene ring.
15:
- The organic electroluminescence device according to claim 5, wherein R3a and R4a of formula (a) are bonded to each other to form a benzofuran or a benzothiophene.
16:
- The organic electroluminescence device according to claim 5, wherein R1a and R2a are bonded to each other to form a benzene ring, and R3a and R4a are bonded to each other to form a benzofuran or a benzothiophene.
17:
- The organic electroluminescence device according to claim 1, wherein the light emitting layer comprises the fused fluoranthene compound.
18:
- The organic electroluminescence device according to claim 1, wherein the organic electroluminescence device comprises an anode-side organic thin film layer between the anode and the light emitting layer, and the anode-side organic thin film layer comprises the fused fluoranthene compound.
19:
- The organic electroluminescence device according to claim 1, wherein the organic electroluminescence device comprises a cathode-side organic thin film layer between the cathode and the light emitting layer, and the cathode-side organic thin film layer comprises the fused fluoranthene compound.
20:
- The organic electroluminescence device according to claim 1, wherein the light emitting layer comprises a phosphorescent material.
21:
- The organic electroluminescence device according to claim 1, wherein the light emitting layer comprises a fluorescent material.
22:
- The organic electroluminescence device according to claim 20, wherein the phosphorescent material is an ortho-metallated complex comprising a metal atom selected from iridium (Ir), osmium (Os), and platinum (Pt).
23:
- An electronic equipment comprising the organic electroluminescence device according to claim 1.
24:
- An organic electroluminescence device, comprising:
- a cathode;
- an anode;
- and
- an organic thin film layer comprising one or more layers disposed between the cathode and the anode,
- wherein the organic thin film layer comprises a light emitting layer and at least one layer of the organic thin film layer comprises a fused fluoranthene compound which is selected from the following compounds 1 to 26:
3 more elements