US 11,925,107 B2
Organic electroluminescent device
Kazuyuki Suruga, Tokyo (JP); Shuichi Hayashi, Tokyo (JP); Takeshi Yamamoto, Tokyo (JP); Kouki Kase, Tokyo (JP); and Shunji Mochizuki, Tokyo (JP)
Assigned to Hodogaya Chemical Co., Ltd., Tokyo (JP)
Appl. No. 16/495,523
Filed by Hodogaya Chemical Co., Ltd., Tokyo (JP)
PCT Filed Mar. 2, 2018, PCT No. PCT/JP2018/008131
§ 371(c)(1), (2) Date Sep. 19, 2019,
PCT Pub. No. WO2018/180215, PCT Pub. Date Oct. 4, 2018.
Claims priority of application No. 2017-063510 (JP), filed on Mar. 28, 2017.
Prior Publication US 2020/0013958 A1, Jan. 9, 2020
Int. Cl. H01L 51/00 (2006.01); C07C 211/54 (2006.01); C07C 211/61 (2006.01); C09K 11/06 (2006.01); H10K 85/60 (2023.01); H10K 50/15 (2023.01); H10K 50/17 (2023.01)
CPC H10K 85/631 (2023.02) [C07C 211/54 (2013.01); C07C 211/61 (2013.01); C09K 11/06 (2013.01); H10K 85/633 (2023.02); C07C 2603/18 (2017.05); C09K 2211/1007 (2013.01); C09K 2211/1011 (2013.01); C09K 2211/1014 (2013.01); H10K 50/15 (2023.02); H10K 50/17 (2023.02); H10K 85/615 (2023.02); H10K 85/626 (2023.02)] 3 Claims
 
1. An organic electroluminescent device comprising at least an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode, in this order, wherein the hole injection layer includes an arylamine compound represented by the following general formula (1) and a radialene derivative represented by the following general formula (2):

OG Complex Work Unit Chemistry
wherein R1 represents 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; R2 and R3 represent 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; r1 to r3 may be the same or different, r1 representing 0 to 5, and r2 and r3 representing 0 to 4, where when r1 is 2 to 5, or when r2 and r3 are 2 to 4, R1 to R3, a plurality of which bind to the same benzene ring, may be the same or different and may bind to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring; Ar1 to Ar3 may be the same or different, and represent a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenylyl, a substituted or unsubstituted terphenylyl, a substituted naphthyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted indenyl, a substituted or unsubstituted pyrenyl, a substituted or unsubstituted perylenyl, a substituted or unsubstituted fluoranthenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted furyl, a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothienyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted benzoxazolyl, a substituted or unsubstituted benzothiazolyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoimidazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothienyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted phenanthrolinyl, a substituted or unsubstituted acridinyl, or a substituted or unsubstituted carbolinyl, and wherein, when Ar1 to Ar3 in the general formula (1) have the substituents, the substituents of Ar1 to Ar3 in the general formula (1) are one or more of cyano; nitro; a halogen atoms; a linear or a branched alkyloxy of 1 to 6 carbon atoms; an aryloxy; an arylalkyloxy; an aromatic hydrocarbon group, a condensed polycyclic aromatic group, or an aromatic heterocyclic group;

OG Complex Work Unit Chemistry
wherein Ar4 to Ar6 may be the same or different, and represent an aromatic hydrocarbon group, an aromatic heterocyclic group, or a condensed polycyclic aromatic group, having an electron acceptor group as a substituent;
and wherein the hole transport layer includes an arylamine compound represented by the general formula (1).