Bis-carbazole derivative and organic electroluminescent element using same

Patent metadata

Field	Value
Publication number	US-9564595-B2
Application number	US-201214006514-A
Country	US
Kind code	B2
Filing date	Mar 21, 2012
Priority date	Mar 24, 2011
Publication date	Feb 7, 2017
Grant date	Feb 7, 2017

Abstract

A biscarbazole derivative represented by formula (1):

wherein A 1 , A 2 , L 1 , L 2 , R 1 to R 4 , and a to d are as defined in the specification, is useful as a material for forming organic EL devices and the organic EL devices including the derivative is capable of driving at a low voltage and has a long lifetime.

First claim

What is claimed is:

1. A biscarbazole derivative represented by formula (1):

wherein:
L 1 and L 2 are identical or different and each independently represents a linker that is a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms;
R 1 to R 4 are identical or different and each independently represents a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, wherein the heteroaryl group is selected from the group consisting of 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 isoxazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, an isobenzofuranyl group, a benzothiophenyl group, an indolizinyl group, a quinolizinyl group, a quinolyl group, an isoquinolinyl group, a cinnolinyl 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a phenothiazinyl group, a phenoxazinyl group, and a xanthenyl group;
adjacent R 1 groups, adjacent R 2 groups, adjacent R 3 groups, and adjacent R 4 groups may be bonded to each other to form a saturated or unsaturated, substituted or unsubstituted divalent group which completes a ring structure;
each of a and d independently represents an integer of 0 to 4;
each of b and c independently represents an integer of 0 to 3;
A 1 represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, wherein the heteroaryl group is selected from the group consisting of 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 isoxazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, an isobenzofuranyl group, a benzothiophenyl group, an indolizinyl group, a quinolizinyl group, a quinolyl group, an isoquinolinyl group, a cinnolinyl 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a phenothiazinyl group, a phenoxazinyl group, and a xanthenyl group;
A 2 represents a group represented by formula (2-1) or (2-2):

wherein:
Ar 1 represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms;
R 5 to R 8 are identical or different and each independently represents a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, or a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms;
adjacent R 5 groups and adjacent R 6 groups may be bonded to each other to form a saturated or unsaturated, substituted or unsubstituted divalent group which completes a ring structure;
f represents an integer of 0 to 4;
g and h are 0;
e represents an integer of 0 to 3; and
L 2 represents a single bond if A 2 is a group represented by formula (2-1), and L 2 represents a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms if A 2 is a group represented by formula (2-2).

2. The biscarbazole derivative according to claim 1 , wherein the biscarbazole derivative is represented by formula (3-1), (3-2), or (3-3):

3. The biscarbazole derivative according to claim 1 , wherein the biscarbazole derivative is represented by formula (3-4):

4. The biscarbazole derivative according to claim 1 , wherein A 2 is represented by formula (2-3) or (2-4):

5. The biscarbazole derivative according to claim 1 , wherein L 2 represents an arylene group having 6 to 30 ring carbon atoms, wherein the arylene group is a divalent residue of an aromatic compound selected from the group consisting of benzene, biphenyl, naphthalene, phenanthrene, fluorene, and 9,9-dimethylfluorene.

6. The biscarbazole derivative according to claim 1 , wherein L 2 represents a substituted or unsubstituted 1,4-phenylene group.

7. The biscarbazole derivative according to claim 1 , wherein L 2 represents a substituted or unsubstituted 1,3-phenylene group.

8. The biscarbazole derivative according to claim 1 , wherein L 2 represents a substituted or unsubstituted 9,9-dimethylfluorene-2,7-diyl group.

9. The biscarbazole derivative according to claim 1 , wherein the heteroaryl group having 5 to 30 ring atoms for R 1 to R 4 and A 1 is selected from the group consisting of a furyl group, a thienyl group, a benzofuranyl group, a benzothiophenyl group, dibenzofuranyl group, and a dibenzothiophenyl group.

10. A material suitable for an organic electroluminescence device, the material comprising the biscarbazole derivative according to claim 1 .

11. A hole transporting material comprising the biscarbazole derivative according to claim 1 .

Assignees

• Kato Tomoki
• Yabunouchi Nobuhiro
• Fujiyama Takahiro
• Idemitsu Kosan Co

Inventors

• Kato Tomoki
• Yabunouchi Nobuhiro
• Fujiyama Takahiro

Classifications

• H01L51/0087

  Electricity · mapped topic

• H01L51/0072

  Electricity · mapped topic

• H01L51/0085

  Electricity · mapped topic

• C07D209/88

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system · CPC title

• C07D209/86 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title