US 10,892,420 B2
Organic electroluminescent device
Shuichi Hayashi, Tokyo (JP); Naoaki Kabasawa, Tokyo (JP); Soon-wook Cha, Cheongju-si (KR); Sang-woo Park, Cheongju-si (KR); Ju-man Song, Cheongju-si (KR); and Kyung-seok Jeon, Cheongju-si (KR)
Assigned to Hodogaya Chemical Co., Ltd., Tokyo (JP); and SFC Co., Ltd., Cheongju-si (KR)
Appl. No. 15/525,134
Filed by Hodogaya Chemical Co., Ltd., Tokyo (JP); and SFC Co., Ltd., Cheongju-si (KR)
PCT Filed Nov. 6, 2015, PCT No. PCT/JP2015/005572
§ 371(c)(1), (2) Date May 8, 2017,
PCT Pub. No. WO2016/079944, PCT Pub. Date May 26, 2016.
Claims priority of application No. 2014-233722 (JP), filed on Nov. 18, 2014.
Prior Publication US 2018/0277761 A1, Sep. 27, 2018
Int. Cl. H01L 51/00 (2006.01); H01L 51/50 (2006.01); C07C 211/54 (2006.01); C07C 211/58 (2006.01); C07C 211/61 (2006.01); C07D 493/10 (2006.01); C07D 307/77 (2006.01); C09K 11/06 (2006.01); C09B 57/00 (2006.01); C07D 209/14 (2006.01); C07D 209/96 (2006.01); C07D 495/10 (2006.01); C07F 7/08 (2006.01); C07D 495/04 (2006.01); C07D 209/80 (2006.01)
CPC H01L 51/006 (2013.01) [C07C 211/54 (2013.01); C07C 211/58 (2013.01); C07C 211/61 (2013.01); C07D 209/14 (2013.01); C07D 209/96 (2013.01); C07D 307/77 (2013.01); C07D 493/10 (2013.01); C07D 495/10 (2013.01); C07F 7/0812 (2013.01); C09B 57/008 (2013.01); C09K 11/06 (2013.01); H01L 51/0052 (2013.01); H01L 51/0059 (2013.01); H01L 51/0061 (2013.01); H01L 51/0071 (2013.01); H01L 51/0072 (2013.01); H01L 51/0094 (2013.01); H01L 51/50 (2013.01); C07C 2603/18 (2017.05); C07C 2603/42 (2017.05); C07C 2603/97 (2017.05); C07D 209/80 (2013.01); C07D 495/04 (2013.01); C09K 2211/1007 (2013.01); C09K 2211/1011 (2013.01); C09K 2211/1014 (2013.01); C09K 2211/1018 (2013.01); H01L 51/0054 (2013.01); H01L 51/0058 (2013.01); H01L 51/0073 (2013.01); H01L 51/0085 (2013.01); H01L 51/5012 (2013.01); H01L 51/5016 (2013.01); H01L 51/5056 (2013.01); H01L 51/5064 (2013.01); H01L 51/5072 (2013.01)] 14 Claims
 
1. An organic electroluminescent 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 has a two-layer structure of a first hole transport layer and a second hole transport layer, and the second hole transport layer comprises an arylamine compound of general formula (1):

OG Complex Work Unit Drawing
wherein Ar1 to Ar4 may be the same or different, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group;
and the light emitting layer comprises an amine derivative of general formula (2a-a), (2a-b), (2b-a), (2b-b), (2b-c), (2b-d), (2c-a) or (2c-b), having a condensed ring structure:

OG Complex Work Unit Drawing

OG Complex Work Unit Drawing
wherein A1 represents a divalent group of a substituted or unsubstituted aromatic hydrocarbon, a divalent group of a substituted or unsubstituted aromatic heterocyclic ring, a divalent group of substituted or unsubstituted condensed polycyclic aromatics, or a single bond;
Ar5 and Ar6 may be the same or different, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, where Ar5 and Ar6 may bind to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring;
X and Y may be the same or different, each representing an oxygen atom or a sulfur atom;
R1 to R4 may be the same or different, and represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano, nitro, linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkenyl of 2 to 6 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy 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, substituted or unsubstituted aryloxy, or a disubstituted amino group substituted with a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group, and a condensed polycyclic aromatic group, where R1 to R4 may bind to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring, and R1 to R4 and the benzene ring binding with R1 to R4 may bind to each other via substituted or unsubstituted methylene, an oxygen atom, a sulfur atom, or a mono-substituted amino group;
R5 to R7 may be the same or different, represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano, nitro, linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkenyl of 2 to 6 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy 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 substituted or unsubstituted aryloxy, wherein at least one of R5 to R7 is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, and where R5 to R7 may bind to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring, and R5 to R7 and the benzene ring binding with R5 to R7 may bind to each other via substituted or unsubstituted methylene, an oxygen atom, a sulfur atom, or a mono-substituted amino group; and
R8 and R9 may be the same or different, linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkenyl of 2 to 6 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 substituted or unsubstituted aryloxy, where R8 and R9 may bind to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, a sulfur atom, or a mono-substituted amino group to form a ring.