Organic electroluminescent device

Patent metadata

Field	Value
Publication number	US-9812661-B2
Application number	US-201313909138-A
Country	US
Kind code	B2
Filing date	Jun 4, 2013
Priority date	May 22, 2009
Publication date	Nov 7, 2017
Grant date	Nov 7, 2017

Abstract

An organic electroluminescence device including at least an anode, an emitting layer, an electron-transporting region and a cathode in sequential order, wherein the emitting layer contains a host and a dopant which gives fluorescent emission of which the main peak wavelength is 550 nm or less; the affinity Ad of the dopant is equal to or larger than the affinity Ah of the host; the triplet energy E T d of the dopant is larger than the triplet energy E T h of the host; and a blocking layer is provided within the electron-transporting region such that it is adjacent to the emitting layer, and the triplet energy E T b of the blocking layer is larger than E T h .

First claim

The invention claimed is:

1. An organic electroluminescence device comprising at least an anode, an emitting layer, an electron-transporting region and a cathode in sequential order, wherein
the emitting layer contains a host represented by the following formula (10) and a dopant which gives fluorescent emission of which the main peak wavelength is 550 nm or less;
the affinity Ad of the dopant is equal to or larger than the affinity Ah of the host;
the triplet energy E T d of the dopant is larger than the triplet energy E T h of the host; and
a blocking layer is provided within the electron-transporting region such that it is adjacent to the emitting layer,
the blocking layer comprises a polycyclic aromatic compound having a skeleton part selected from the group consisting of compounds shown by the following formulas (1), (3), and (4) optionally comprising a substituent selected from the group consisting of a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group or a carboxyl group; and a polycyclic aromatic compound represented by the following formula (10A); and
the triplet energy E T b of the polycyclic aromatic compound is larger than E T h :

wherein in formula (10), Ar 11 and Ar 12 are independently a substituted or unsubstituted aryl group having 6 to 50 carbon atoms that form a ring or a substituted or unsubstituted hetrocyclic group having 5 to 50 ring atoms, and
R 1 to R 8 are independently a group selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted hetrocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group and a hydroxyl group

wherein in formulas (1), (3), and (4), Ar 1 , and Ar 3 to Ar 5 are a substituted or unsubstituted condensed ring structure having 4 to 16 ring carbon atom,

wherein in formula (10A), X 13 to X 18 , X 20 and X 21 are independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aryl group, and X 12 and X 19 are independently a hydrogen atom, a halogen atom, a linear, branched, or cyclic alkyl group, a liner, branched or cyclic alkoxy group.

2. The organic electroluminescence device according to claim 1 , wherein the dopant is a compound selected from fluoranthene derivatives and boron complexes.

3. The organic electroluminescence device according to claim 1 further comprising a hole-transporting region between the anode and the emitting layer, wherein a hole-transporting layer is provided in the hole-transporting region such that it is adjacent to the emitting layer, and the triplet energy E T ho of the hole-transporting layer is larger than E T h .

4. The organic electroluminescence device according to claim 1 , wherein the electron-transporting region is a multilayer stack of the blocking layer and an electron-injecting layer, and the affinity Ab of the blocking layer and the affinity Ae of the electron-injecting layer satisfy the relationship shown by Ae-Ab<0.2 eV.

5. The organic electroluminescence device according to claim 1 , wherein the electron-transporting region is a single blocking layer.

6. The organic electroluminescence device according to claim 1 , wherein the electron-transporting region is a single blocking layer which is doped with a donor.

7. The organic electroluminescence device according to claim 1 , wherein the host is a compound which does not contain a double bond in other parts than a ring structure.

8. The organic electroluminescence device according to claim 1 , wherein the dopant is a compound which does not contain a double bond in other parts than a ring structure.

9. The organic electroluminescence device according to claim 1 , which comprises at least two emitting layers between the anode and the cathode and an intermediate layer between two emitting layers.

10. The organic electroluminescence device according to claim 1 , which comprises a plurality of emitting layers between the anode and the cathode and a carrier-blocking layer between a first emitting layer and a second emitting layer.

11. The organic electroluminescence device according to claim 1 , wherein in the formula (10), Ar 11 and Ar 12 are independently phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-naphthacenyl, 2-naphthacenyl, 9-naphthacenyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 6-chrysenyl, 1-benzo[c]phenanthryl, 2-benzo[c]phenanthryl, 3-benzo[c]phenanthryl, 4-benzo[c]phenanthryl, 5-benzo[c]phenanthryl, 6-benzo[c]phenanthryl, 1-benzo[g]chrysenyl, 2-benzo[g]chrysenyl, 3-benzo[g]chrysenyl, 4-benzo[g]chrysenyl, 5-benzo[g]chrysenyl, 6-benzo[g]chrysenyl, 7-benzo[g]chrysenyl, 8-benzo[g]chrysenyl, 9-benzo[g]chrysenyl, 10-benzo[g]chrysenyl, 11-benzo[g]chrysenyl, 12-benzo[g]chrysenyl, 13-benzo[g]chrysenyl, 14-benzo[g]chrysenyl, 1-triphenyl, 2-triphenyl, 2-fluorenyl, 9,9-dimethylfluorene-2-yl, benzofluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-t-butylphenyl, p-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl, 4-methyl-1-anthryl, 4′-methylbiphenylyl, 4″-t-butyl-p-terphenyl-4-yl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, 1-phenantridin

Assignees

• Idemitsu Kosan Co

Inventors

• Kuma Hitoshi
• Kawamura Yuichiro
• Jinde Yukitoshi
• Ogiwara Toshinari
• Hosokawa Chishio

Classifications

• B82Y10/00 Primary

  Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic · CPC title

• H01L51/5016

  Electricity · mapped topic

• H01L51/0048

  Electricity · mapped topic

• C09B57/00 Primary

  Other synthetic dyes of known constitution · CPC title

• H01L51/0072

  Electricity · mapped topic