Organic electroluminescent device
The present inventors have focused the fact that an arylamine material having a specific structure is excellent in hole injection/transport ability, thin film stability and durability. The arylamine compound of the above can be selected as a material for the hole transport layer, holes injected from the anode side can be efficiently transported. Furthermore, various organic EL devices combining electron transport materials having a specific structure and the like were manufactured, and the characteristics of the devices were evaluated diligently.
1 . An organic electroluminescence device comprising at least an anode, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode in this order, wherein the hole transport layer comprises an arylamine compound of the following general formula (1):
wherein R 1 and R 2 represent a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group of 1 to 6 carbon atoms that may have a substituent, a cycloalkyl group of 5 to 10 carbon atoms that may have a substituent, a linear or branched alkenyl group of 2 to 6 carbon atoms that may have a substituent, a linear or branched alkyloxy group of 1 to 6 carbon atoms that may have a substituent, a cycloalkyloxy group of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group; R 3 represents a hydrogen atom; A 1 represents a divalent group of a substituted or unsubstituted aromatic hydrocarbon, a divalent group of a substituted or unsubstituted aromatic heterocyclic ring, or a divalent group of substituted or unsubstituted condensed polycyclic aromatics; Ar 1 to Ar 2 represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; Ar 3 represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted indoyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzooxazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted phenanthrolinyl, acridinyl group, or a substituted or unsubstituted carbolinyl group; r 1 and r 2 represent integers from 0 to 4; and
wherein the light emitting layer includes a blue light emitting dopant, and wherein the blue light emitting dopant is a compound represented by the following general formula (2) or general formula (3):
wherein, Q 1 to Q 3 may be the same or different, and represent a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted condensed polycyclic aromatics, or a substituted or unsubstituted aromatic heterocyclic ring; X represents B, P, P═O, or P═S; Y 1 to Y 3 may be the same or different, and represent one of selected from N—R 4 , CR 5 R 6 , O, S, Se and SiR 7 R 8 ; R 4 to R 8 may be the same or different, and represent hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group of 1 to 6 carbon atoms that may have a substituent, a cycloalkyl group of 5 to 10 carbon atoms that may have a substituent, a linear or branched alkenyl group of 2 to 6 carbon atoms that may have a substituent, a linear or branched alkyloxy group of 1 to 6 carbon atoms that may have a substituent, a cycloalkyloxy group of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group; R 5 and R 6 , and R 7 and R 8 may bind to each other to form a ring via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom; when Y 1 to Y 3 are N—R 4 , CR 5 R 6 , or SiR 7 R 8 , R 4 to R 8 may bind to Q 1 , Q 2 , or Q 3 , which adjacent to R 4 to R 8 respectively, to form a ring via a linking group, such as substituted or unsubstituted methylene, an oxygen atom, a sulfur atom, or a monosubstituted amino group.
2 . The organic electroluminescent device according to claim 1 , wherein the hole transport layer has a two-layer structure of a first hole transport layer and a second hole transport layer, and the second hole transport layer includes the arylamine compound of the general formula (1).
3 . The organic electroluminescent device according to claim 1 , wherein the arylamine compound represented by the general formula (1) is an arylamine compound represented by the following general formula (1a):
wherein A 1 and Ar 1 to Ar 3 are as defined by the general formula (1).
4 . The organic electroluminescent device according to claim 1 , wherein Ar 3 in the general formula (1) or the general formula (1a) represents a substituted or unsubstituted phenyl group.
5 . The organic electroluminescent device according to claim 1 , wherein A 1 in the general formula (1) or the general formula (1a) represents a divalent group that results from the removal of two hydrogen atoms from substituted or unsubstituted benzene.
6 . The organic electroluminescent device according to claim 1 , wherein the light emitting layer includes an anthracene derivative having an anthracene skeleton in the molecule.
7 . The organic electroluminescent device according to claim 6 , wherein the light emitting layer includes a host material that is an anthracene derivative having an anthracene skeleton in the molecule.
8 . The organic electroluminescent device according to claim 2 , wherein the arylamine compound represented by the general formula (1) is an arylamine compound represented by the following general formula (1a);
wherein A 1 and Ar 1 to Ar 3 are as defined by the general formula (1).
9 . The organic electroluminescent device according to claim 2 , wherein Ar 3 in the general formula (1) or the general formula (1a) represents a substituted or unsubstituted phenyl group.
10 . The organic electroluminescent device according to claim 3 , wherein Ar 3 in the general formula (1) or the general formula (1a) represents a substituted or unsubstituted phenyl group.
11 . The organic electroluminescent device according to claim 2 , wherein A 1 in the general formula (1) or the general formula (1a) represents a divalent group that results from the removal of two hydrogen atoms from substituted or unsubstituted benzene.
12 . The organic electroluminescent device according to claim 3 , wherein A 1 in the general formula (1) or the general formula (1a) represents a divalent group that results from the removal of two hydrogen atoms from substituted or unsubstituted benzene.
13 . The organic electroluminescent device according to claim 4 , wherein A 1 in the general formula (1) or the general formula (1a) represents a divalent group that results from the removal of two hydrogen atoms from substituted or unsubstituted benzene.