Organic light emitting device

Abstract

An organic light-emitting device, including a first electrode; a second electrode facing the first electrode; an emission layer between the first electrode and the second electrode; a hole transport region between the first electrode and the emission layer; and an electron transport region between the second electrode and the emission layer, the hole transport region including a compound represented by Formula 1 below and a compound represented by Formula 2 below:

1 .- 20 . (canceled) 
     
     
         21 . An organic light-emitting device, comprising:
 a first electrode;   a second electrode facing the first electrode; and   an organic layer between the first electrode and the second electrode,   the organic layer including one emission layer and a compound represented by Formula 1 below and a compound represented by Formula 2 below:   
       
         
           
           
               
               
           
         
         wherein in Formula 1, 
         Y 1  to Y 5  are each independently a nitrogen (N) atom or —CR 21 , and each R 21  is the same or different from each other; 
         C 1  and C 2  are each a carbon (C) atom; 
         Ring A is an aromatic ring represented by Formula 1a below, and Ring B is an aromatic ring represented by Formula 1b below and condensed with Ring A; 
       
       
         
           
           
               
               
           
         
         wherein the bond between 7 and 8 in Ring B represented by Formula 1b is condensed with the bond between 3 and 4, the bond between 4 and 5, or the bond between 5 and 6 in Ring A represented by Formula 1a, 
         X in Formula 1b is selected from —CR 28 R 29 , —NR 30 , and an —O— atom, 
         wherein in Formula 1, Formula 2, Formula 1a, and Formula 1 b, 
         L 1  and L 2  are each independently selected from a direct bond, a C 6 -C 40  arylene group, and a C 2 -C 40  heteroarylene group; and a C 6 -C 40  arylene group and a C 2 -C 40  heteroarylene group, each substituted with one or more of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20  alkyl group, a C 2 -C 20  alkenyl group, a C 2 -C 20  alkynyl group, a C 1 -C 20  alkoxy group, a C 3 -C 10  cycloalkyl group, a C 3 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 3 -C 10  heterocycloalkenyl group, a C 6 -C 40  aryl group, a C 2 -C 40  heteroaryl group, a C 6 -C 40  aryloxy group, or a C 6 -C 40  arylthio group; 
         R 1  to R 30  are each independently selected from a hydrogen, a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20  alkyl group, a C 2 -C 20  alkenyl group, a C 2 -C 20  alkynyl group, a C 1 -C 20  alkoxy group, a C 3 -C 10  cycloalkyl group, a C 3 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 3 -C 10  heterocycloalkenyl group, a C 6 -C 40  aryl group, a C 2 -C 40  heteroaryl group, a C 6 -C 40  aryloxy group, and a C 6 -C 40  arylthio group; 
         a C 1 -C 40  alkyl group, a C 2 -C 40  alkenyl group, a C 2 -C 40  alkynyl group, and a C 1 -C 40  alkoxy group, each substituted with one or more of a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 3 -C 10  cycloalkyl group, a C 3 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 3 -C 10  heterocycloalkenyl group, a C 6 -C 40  aryl group, a C 2 -C 40  heteroaryl group, a C 6 -C 40  aryloxy group, or a C 6 -C 40  arylthio group; and 
         a C 3 -C 10  cycloalkyl group, a C 3 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 3 -C 10  heterocycloalkenyl group, a C 6 -C 40  aryl group, a C 2 -C 40  heteroaryl group, a C 6 -C 40  aryloxy group, and C 6 -C 40  arylthio group, each substituted with one or more of a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20  alkyl group, a C 2 -C 20  alkenyl group, a C 2 -C 20  alkynyl group, a C 1 -C 20  alkoxy group, a C 3 -C 10  cycloalkyl group, a C 3 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 3 -C 10  heterocycloalkenyl group, a C 6 -C 40  aryl group, a C 2 -C 40  heteroaryl group, a C 6 -C 40  aryloxy group, or a C 6 -C 40  arylthio group, 
         wherein respective portions of R 1  to R 4  may be bound to one other so as to be condensed to the ring to which the substituents R 1  to R 4  are attached. 
       
     
     
         22 . The organic light-emitting device of  claim 21 , wherein
 the organic layer includes a hole transport region between the first electrode and the emission layer and an electron transport region between the second electrode and the emission layer.   
     
     
         23 . The organic light-emitting device as claimed in  claim 22 , wherein the hole transport region includes one or more of a hole transport layer, a hole injection layer, a hole injection transport layer, or an auxiliary layer. 
     
     
         24 . The organic light-emitting device as claimed in  claim 21 , wherein the electron transport region includes one or more of a hole blocking layer, an electron transport layer, an electron injection layer, or an electron injection transport layer. 
     
     
         25 . The organic light-emitting device as claimed in  claim 21 , wherein green light is emitted from the emission layer. 
     
     
         26 . The organic light-emitting device as claimed in  claim 21 , wherein
 L 1  and L 2  are each independently selected from a direct bond, a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, an indacenylene group, an acenaphthylene group, a phenalenylene group, a fluorenylene group, a phenanthrenylene group, an anthrylene group, a fluoranthenylene group, a pyrenylene group, a naphthacenylene group, a chrysenylene group, a triphenylenylene group, a pyrrolylene group, an imidazolylene group, a pyrazolylene group, a pyridylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolylene group, a quinazolinylene group, a carbazolylene group, a dibenzofuranylene group, and a dibenzothiophenylene group; and   a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, an indacenylene group, an acenaphthylene group, a biphenylene group, a phenalenylene group, a fluorenylene group, a phenanthrenylene group, an anthrylene group, a fluoranthenylene group, a pyrenylene group, a benzofluorenylene group, a naphthacenylene group, a chrysenylene group, a triphenylenyl group, a pyrrolylene group, an imidazolylene group, a pyrazolylene group, a pyridylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolylene group, a carbazolylene group, a dibenzofuranylene group, and a dibenzothiophenylene group, each substituted with one or more of a deuterium, a halogen atom, a hydroxyl group, a cyano group, an amino group, a C 1 -C 20  alkyl group, a C 2 -C 20  alkenyl group, a C 2 -C 20  alkynyl group, a C 1 -C 20  alkoxy group, a C 3 -C 10  cycloalkyl group, a C 3 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 3 -C 10  heterocycloalkenyl group, a C 6 -C 40  aryl group, a C 2 -C 40  heteroaryl group, a C 6 -C 40  aryloxy group, or a C 6 -C 40  arylthio group.   
     
     
         27 . The organic light-emitting device as claimed in  claim 21 , wherein L 1  and L 2  are each independently selected from a direct bond and groups represented by Formulae 3A and 3B: 
       
         
           
           
               
               
           
         
         wherein * indicates a binding site. 
       
     
     
         28 . The organic light-emitting device as claimed in  claim 21 , wherein
 R 1  to R 30  are each independently selected from a hydrogen, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a biphenyl group, a heptalenyl group, a phenalenyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a fluoranthenyl group, a pyrenyl group, a pyrrolyl group, a furyl group, a pyrazolyl group, an imidazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a benzofuryl group, an isobenzofuryl group, an indazolyl group, a benzimidazolyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a carbazolyl group, a benzocarbazolyl group, and a pyridoindolyl group; and   a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a biphenyl group, a heptalenyl group, a phenalenyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a fluoranthenyl group, a pyrenyl group, a pyrrolyl group, a furyl group, a pyrazolyl group, an imidazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a benzofuryl group, an isobenzofuryl group, an indazolyl group, a benzimidazolyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a carbazolyl group, a benzocarbazolyl group, and a pyridoindolyl group, each substituted with one or more of a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20  alkyl group, a C 2 -C 20  alkenyl group, a C 2 -C 20  alkynyl group, a C 1 -C 20  alkoxy group, a C 3 -C 10  cycloalkyl group, a C 3 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 3 -C 10  heterocycloalkenyl group, a C 6 -C 40  aryl group, a C 2 -C 40  heteroaryl group, a C 6 -C 40  aryloxy group, or a C 6 -C 40  arylthio group.   
     
     
         29 . The organic light-emitting device as claimed in  claim 21 , wherein
 R 1  to R 30  are each independently selected from a hydrogen atom, a methyl group, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinazolinyl group; and   a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, and a quinazolinyl group, each substituted with one or more of a methyl group, an ethyl group, a butyl group, a phenyl group, a biphenyl group, a pyridyl group, a quinolyl group, or a carbazolyl group.   
     
     
         30 . The organic light-emitting device as claimed in  claim 21 , wherein
 R 1  to R 30  are each independently selected from a hydrogen atom and groups represented by Formulae 4A to 4F below:   
       
         
           
           
               
               
           
         
         wherein in Formulae 4A to 4F, 
         Z 11  to Z 16  are each independently selected from a deuterium atom, a halogen atom, a C 1 -C 20  alkyl group, a C 1 -C 20  alkoxy group, a C 6 -C 40  aryl group, and a C 2 -C 40  heteroaryl group; 
         a C 1 -C 20  alkyl group and a C 1 -C 20  alkoxy group, each substituted with one or more of a deuterium atom or a halogen atom; and 
         a C 6 -C 40  aryl group and a C 2 -C 40  heteroaryl group, each substituted with one or more of a deuterium atom, a halogen atom, a C 1 -C 20  alkyl group, a C 1 -C 20  alkoxy group, a C 6 -C 20  aryl group, or a C 2 -C 20  heteroaryl group; 
         p1 is an integer selected from 1 to 5, 
         p2 is an integer selected from 1 to 4, 
         p3 is an integer selected from 1 to 3, 
         p4 is an integer selected from 1 to 2, 
         p5 is an integer selected from 1 to 6, 
         p6 is an integer selected from 1 to 5, and 
         * indicates a binding site. 
       
     
     
         31 . The organic light-emitting device as claimed in  claim 30 , wherein
 Z 11  to Z 16  are each independently selected from groups represented by Formulae 5A to 5D:   
       
         
           
           
               
               
           
         
         wherein in Formulae 5A to 5D, k indicates a binding site. 
       
     
     
         32 . The organic light-emitting device as claimed in  claim 21 , wherein
 R 1  to R 30  are each independently selected from groups represented by Formulae 6A to 6L below:   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         33 . The organic light-emitting devices as claimed in  claim 21 , wherein
 R 1  to R 10 , R 12  to R 17 , R 19  to R 21 , R 24  to R 27 , and R 30  are each independently selected from groups represented by Formulae 6A to 6L below:   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         34 . The organic light-emitting device as claimed in  claim 21 , wherein
 the compound represented by Formula 1 includes one or more of the compounds below:   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       and
 the compound represented by Formula 2 includes one or more of the compounds below: 
 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         35 . The organic light-emitting device as claimed in  claim 23 , wherein
 the hole transport layer includes compounds represented by Formulae 201A and 202A below.   
       
         
           
           
               
               
           
         
         wherein in Formulae 201A and 202A, 
         L 201  to L 203  is selected from a substituted or unsubstituted C 3 -C 10  cycloalkylene group, a substituted or unsubstituted C 3 -C 10  heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10  cycloalkenylene group, a substituted or unsubstituted C 3 -C 10  heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60  arylene group, a substituted or unsubstituted C 2 -C 60  heteroarylene group, and a substituted or unsubstituted divalent C 6 -C 60  non-aromatic condensed polycyclic group, 
         xa1 to xa3 is selected from 0, 1, 2, and 3, and xa5 is selected from 1,2, 3, 4, and 5, 
         R 202  to R 204 , R 211 , and R 212  are each independently selected from a substituted or unsubstituted C 3 -C 1I  cycloalkyl group, a substituted or unsubstituted C 3 -C 10  heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10  cycloalkenyl group, a substituted or unsubstituted C 3 -C 10  heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60  aryl group, a substituted or unsubstituted C 2 -C 60  heteroaryl group, and a substituted or unsubstituted monovalent C 6 -C 30  non-aromatic condensed polycyclic group, and 
         R 213  to R 216  are each independently selected from a hydrogen, a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 60  alkyl group, a C 2 -C 60  alkenyl group, a C 2 -C 60  alkynyl group, a C 1 -C 60  alkoxy group, a C 3 -C 10  cycloalkyl group, a C 3 -C 1I  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 3 -C 10  heterocycloalkenyl group, a C 6 -C 60  aryl group, a C 6 -C 60  aryloxy group, a C 6 -C 60  arylthio group, a C 2 -C 60  heteroaryl group, and a C 6 -C 60  non-aromatic condensed polycyclic group. 
       
     
     
         36 . The organic light-emitting device as claimed in  claim 35 , wherein
 the compound represented by Formula 201A includes one or more of Compounds HT1 to HT12, and the compound represented by Formula 202A includes one or more of Compounds 301 to 308:   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         37 . The organic light-emitting device as claimed in  claim 35 , wherein green light is emitted from the emission layer. 
     
     
         38 . An organic light-emitting device, comprising:
 a first electrode;   a second electrode facing the first electrode; and   an organic layer between the first electrode and the second electrode,   the organic layer comprising an emission layer and a compound represented by one of Formulae 1-1 to 1-11 below and a compound represented by Formula 2-1 below:   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein in Formulae 1-1 to 1-11 and 2-1, 
         Y 1  to Y 5  are each independently a nitrogen (N) atom or —CR 21 , and each R 21  is the same or different from each other; 
         L 1  and L 2  are selected from a direct bond and a C 6 -C 40  arylene group; 
         R 1  to R 10 , R 12  to R 17 , R 19  to R 21 , R 24  to R 27 , and R 30  are each independently selected from a hydrogen, a C 6 -C 40  aryl group, and a C 2 -C 40  heteroaryl group; and a C 6 -C 40  aryl group and a C 2 -C 40  heteroaryl group, each substituted with one or more of a C 1 -C 20  alkyl group, a C 6 -C 40  aryl group, or a C 2 -C 40  heteroaryl group. 
       
     
     
         39 . The organic light-emitting device as claimed in  claim 38 , wherein
 L 1  and L 2  are each independently selected from a direct bond and groups represented by Formulae 3A and 3B:   
       
         
           
           
               
               
           
         
         wherein * indicates a binding site. 
       
     
     
         40 . The organic light-emitting device as claimed in  claim 38 , wherein
 R 1  to R 10 , R 12  to R 17 , R 19  to R 21 , R 24  to R 27 , and R 30  are each independently selected from a hydrogen atom and groups represented by Formulae 4A to 4F below:   
       
         
           
           
               
               
           
         
         Z 11  to Z 16  are each independently selected from a C 1 -C 20  alkyl group, a C 6 -C 40  aryl group, and a C 2 -C 40  heteroaryl group; 
         p1 is an integer selected from 1 to 5, 
         p2 is an integer selected from 1 to 4, 
         p3 is an integer selected from 1 to 3, 
         p4 is an integer selected from 1 to 2, 
         p5 is an integer selected from 1 to 6, 
         p6 is an integer selected from 1 to 5, and 
         * indicates a binding site.